JP2014136758A - Tread rubber composition and pneumatic tire - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a tread rubber composition capable of achieving a well balanced improvement in low fuel consumption, wet grip performance and wear resistance, and to provide a pneumatic tire using the same.SOLUTION: The present invention relates to a tread rubber composition containing rubber constituent, silica and conductive carbon black, in which the content of a particular conjugated diene-based polymer in 100 mass% of the rubber constituent is 5 mass% or more, the content of the silica for 100 pts.mass of the rubber constituent is 5 to 150 pts.mass, and the content of the conductive carbon black for 100 pts.mass of the rubber constituent is 3 to 30 pts.mass.

Description

The present invention relates to a rubber composition for a tread and a pneumatic tire produced using the rubber composition.

As a rubber composition for an automobile tire, a rubber composition containing a conjugated diene polymer such as polybutadiene or butadiene-styrene copolymer and a filler such as carbon black or silica is used. In recent years, due to increasing interest in environmental issues, there has been a strong demand for lower fuel consumption for automobiles, and rubber compositions used for automobile tires are also required to have excellent fuel efficiency. .

As a method for improving fuel economy, for example, Patent Document 1 proposes a method using a diene rubber (modified rubber) modified with an organosilicon compound containing an amino group and an alkoxy group. However, in recent years, further improvement in fuel economy has been demanded due to an increase in interest in environmental problems. In addition, the performance required for rubber compositions for automobile tires includes wet grip performance and wear resistance, but these performances are generally in contradiction to low fuel consumption. It was difficult to obtain a high dimension and good balance.

Patent Document 2 discloses a rubber composition using conductive carbon black as a technique for increasing the volume resistivity that is likely to occur when carbon black as a reinforcing agent is replaced with silica. Conductive carbon black has a relatively low particle density, and the volume resistivity can be reduced even with the same amount of addition as general-purpose carbon black. This is presumably because a high-order network structure is easily formed due to the low particle density. However, the use of conductive carbon black has not been sufficient in terms of improving fuel efficiency, wet grip performance and wear resistance.

JP 2000-344955 A Japanese Patent No. 3841524

An object of the present invention is to solve the above problems and provide a rubber composition for a tread that can improve fuel economy, wet grip performance, and wear resistance in a well-balanced manner, and a pneumatic tire using the same.

（式中、Ｒ^１１１は水素原子又はヒドロカルビル基を表し、ｍ^１は０又は１であり、Ｒ^１１２はヒドロカルビレン基を表し、Ｘ^１０１、Ｘ^１０２及びＸ^１０３は、それぞれ独立に、置換アミノ基、又は、置換基を有していてもよいヒドロカルビル基を表し、Ｘ^１０１、Ｘ^１０２及びＸ^１０３の少なくとも１つが置換アミノ基である。）

（式中、Ｒ^１２１は水素原子又はヒドロカルビル基を表し、ｎ^１は０又は１であり、Ｒ^１２２はヒドロカルビレン基を表し、Ａ^１０１は置換アミノ基、又は、含窒素複素環基を表す。） 1st this invention contains a rubber component, a silica, and conductive carbon black, the monomer unit based on a conjugated diene in 100 mass% of said rubber components, The compound represented by following formula (11) The content of the conjugated diene polymer (A) having a monomer unit based on the above and a monomer unit based on the compound represented by the following formula (12) is 5% by mass or more, and the rubber component 100 It is related with the rubber composition for treads whose content of the said silica is 5-150 mass parts with respect to a mass part, and whose content of the said conductive carbon black is 3-30 mass parts.

(Wherein R ¹¹¹ represents a hydrogen atom or a hydrocarbyl group, m ¹ is 0 or 1, R ¹¹² represents a hydrocarbylene group, and X ¹⁰¹ , X ¹⁰² and X ¹⁰³ are each independently substituted amino A hydrocarbyl group which may have a group or a substituent, and at least one of X ¹⁰¹ , X ¹⁰² and X ¹⁰³ is a substituted amino group.)

(In the formula, R ¹²¹ represents a hydrogen atom or a hydrocarbyl group, n ¹ is 0 or 1, R ¹²² represents a hydrocarbylene group, and A ¹⁰¹ represents a substituted amino group or a nitrogen-containing heterocyclic group. .)

In the formula (11), R ¹¹¹ is preferably a hydrogen atom, and m ¹ is preferably 0.

（式中、ｒ^１は０〜５の整数を表し、ｒ^１が１から５の整数である場合、（ＣＨ_２）_ｒ１はベンゼン環上の置換基であり、（ＣＨ_２）_ｒ１がＡ^１０１と結合し、ｒ^１が０である場合、（ＣＨ_２）_ｒ１はベンゼン環とＡ^１０１との結合を表す。） In formula (12), R ¹²¹ is a hydrogen atom, n ¹ is 1, R ¹²² is a group represented by the following formula (12-Y), and A ¹⁰¹ is preferably a substituted amino group. .

(Wherein, ^{r 1} represents an integer of 0 to 5, when ^{r 1} is an integer of from 5 to _{1, (CH 2) r1} is a substituent on the benzene _{ring, (CH 2) r1} is ^{A 101} And when r ¹ is 0, (CH ₂ ) _r1 represents a bond between the benzene ring and A ^101. )

The vinyl bond content of the conjugated diene polymer (A) is preferably 20 mol% or more and 70 mol% or less, with the content of the structural unit based on the conjugated diene being 100 mol%.

（式中、Ｖ^２０１は重合性炭素−炭素二重結合を有するヒドロカルビル基を表し、Ｓ^２０１は置換シリル基を表す。）

（式中、Ｖ^２０２は重合性炭素−炭素二重結合を有するヒドロカルビル基を表し、Ａ^２０２は置換アミノ基、又は、含窒素複素環基を表す。） 2nd this invention contains a rubber component, a silica, and electroconductive carbon black, the monomer unit based on a conjugated diene in 100 mass% of said rubber components, The compound represented by following formula (21) A conjugated diene polymer (B) obtained by reacting an alkoxysilane compound with one end of a copolymer having a monomer unit based on the above and a monomer unit based on a compound represented by the following formula (22) ) Is 5 mass% or more, the silica content is 5 to 150 parts by mass, and the conductive carbon black content is 3 to 30 parts by mass with respect to 100 parts by mass of the rubber component. The present invention relates to a rubber composition for treads.

(In the formula, V ²⁰¹ represents a hydrocarbyl group having a polymerizable carbon-carbon double bond, and S ²⁰¹ represents a substituted silyl group.)

(In the formula, V ²⁰² represents a hydrocarbyl group having a polymerizable carbon-carbon double bond, and A ²⁰² represents a substituted amino group or a nitrogen-containing heterocyclic group.)

（式中、ｐ^２は１〜１０の整数を表し、Ｒ^２３１、Ｒ^２３２及びＲ^２３３は、それぞれ独立にアルキル基又はアルコキシ基を表し、Ｒ^２３１、Ｒ^２３２及びＲ^２３３の少なくとも１つがアルコキシ基であり、Ａ^２０３は置換アミノ基を表す。） The alkoxysilane compound is preferably a compound represented by the following formula (23).

(In the formula, p ² represents an integer of 1 to 10, R ²³¹ , R ²³² and R ²³³ each independently represents an alkyl group or an alkoxy group, and at least one of R ²³¹ , R ²³² and R ²³³ is an alkoxy group. And A ²⁰³ represents a substituted amino group.)

（式中、Ｒ^２１１は水素原子又はヒドロカルビル基を表し、ｎ^２は０又は１であり、Ｒ^２１２はヒドロカルビレン基を表す。）

（式中、Ｘ^２０１、Ｘ^２０２及びＸ^２０３は、それぞれ独立に、置換アミノ基、又は、置換基を有していてもよいヒドロカルビル基を表し、Ｘ^２０１、Ｘ^２０２及びＸ^２０３の少なくとも１つが置換アミノ基である。） The group represented by V ²⁰¹ in the formula (21) is a group represented by the following formula (21-V1), and the group represented by S ²⁰¹ in the formula (21) is represented by the following formula (21-S It is preferable that it is group represented by.

(Wherein R ²¹¹ represents a hydrogen atom or a hydrocarbyl group, n ² is 0 or 1, and R ²¹² represents a hydrocarbylene group.)

(Wherein, X ²⁰¹ , X ²⁰² and X ²⁰³ each independently represent a substituted amino group or a hydrocarbyl group which may have a substituent, wherein at least one of X ²⁰¹ , X ²⁰² and X ²⁰³ is A substituted amino group.)

In the formula (21-V1), R ²¹¹ is preferably a hydrogen atom and n ² is preferably 0.

（式中、Ｒ^２２１は水素原子又はヒドロカルビル基を表し、ｍ^２は０又は１であり、Ｒ^２２２はヒドロカルビレン基を表す。） The group represented by V ²⁰² in the formula (22) is preferably a group represented by the following formula (2-V1).

(Wherein R ²²¹ represents a hydrogen atom or a hydrocarbyl group, m ² represents 0 or 1, and R ²²² represents a hydrocarbylene group.)

（式中、Ｒ^２２５及びＲ^２２６は、それぞれ、ヒドロカルビル基、又は、トリヒドロカルビルシリル基、あるいは、Ｒ^２２５とＲ^２２６とが結合して、窒素原子及び／又は酸素原子をヘテロ原子として有していてもよいヒドロカルビレン基、又は、Ｒ^２２５とＲ^２２６は１つの基であって、窒素原子に二重結合で結合する基を表す。） It is preferable that the substituted amino group of A ^{202 in} the formula (22) is a group represented by the following formula (22-A).

(In the formula, each of R ²²⁵ and R ²²⁶ has a hydrocarbyl group, a trihydrocarbyl silyl group, or R ²²⁵ and R ²²⁶ bonded to each other, and has a nitrogen atom and / or an oxygen atom as a hetero atom. The hydrocarbylene group that may be substituted, or R ²²⁵ and R ²²⁶ are one group and represent a group bonded to the nitrogen atom with a double bond.)

The vinyl bond content of the conjugated diene polymer (B) is preferably 20 mol% or more and 70 mol% or less, with the content of the structural unit based on the conjugated diene being 100 mol%.

（式中、Ｖ^３０１は重合性炭素−炭素二重結合を有するヒドロカルビル基を表し、Ｓ^３０１は置換シリル基を表す。）

（式中、Ｖ^３０２は重合性炭素−炭素二重結合を有するヒドロカルビル基を表し、Ａ^３０２は置換アミノ基、又は、含窒素複素環基を表す。）
化合物（Ｇ）：置換基を有していてもよいアミノ基及びカルボニル基を有する化合物、並びに置換基を有していてもよいアミノ基及びチオカルボニル基を有する化合物からなる化合物群から選ばれる少なくとも１種の化合物。 3rd this invention contains a rubber component, a silica, and electroconductive carbon black, The monomer unit based on a conjugated diene in 100 mass% of said rubber components, The compound represented by following formula (31) And a monomer unit based on the compound represented by the following formula (32), wherein at least one end of the copolymer is modified by the following compound (G). The content of the coalesced (C) is 5% by mass or more, the content of the silica is 5 to 150 parts by mass, and the content of the conductive carbon black is 3 to 30% by mass with respect to 100 parts by mass of the rubber component. It is related with the rubber composition for treads which is a part.

(In the formula, V ³⁰¹ represents a hydrocarbyl group having a polymerizable carbon-carbon double bond, and S ³⁰¹ represents a substituted silyl group.)

(In the formula, V ³⁰² represents a hydrocarbyl group having a polymerizable carbon-carbon double bond, and A ³⁰² represents a substituted amino group or a nitrogen-containing heterocyclic group.)
Compound (G): at least selected from the group consisting of a compound having an amino group and a carbonyl group which may have a substituent, and a compound having an amino group and a thiocarbonyl group which may have a substituent One compound.

（式中、Ｒ^３２１は水素原子又はヒドロカルビル基を表し、ｍ^３は０又は１であり、Ｒ^３２２はヒドロカルビレン基を表す。） The group represented by V ³⁰² in the formula (32) is preferably a group represented by the following formula (32-V1).

(Wherein R ³²¹ represents a hydrogen atom or a hydrocarbyl group, m ³ represents 0 or 1, and R ³²² represents a hydrocarbylene group.)

（式中、Ｒ^３２５及びＲ^３２６は、それぞれ、ヒドロカルビル基、又は、トリヒドロカルビルシリル基、あるいは、Ｒ^３２５とＲ^３２６とが結合して、窒素原子及び／又は酸素原子をヘテロ原子として有していてもよいヒドロカルビレン基、又は、Ｒ^３２５とＲ^３２６は１つの基であって、窒素原子に二重結合で結合する基を表す。） The substituted amino group of A ³⁰² in the formula (32) is preferably a group represented by the following formula (32-A).

(In the formula, R ³²⁵ and R ³²⁶ each have a hydrocarbyl group, a trihydrocarbyl silyl group, or R ³²⁵ and R ³²⁶ bonded to each other and have a nitrogen atom and / or an oxygen atom as a hetero atom. The hydrocarbylene group which may be substituted, or R ³²⁵ and R ³²⁶ are one group and represent a group bonded to the nitrogen atom with a double bond.)

（式中、Ｅは、酸素原子又は硫黄原子を表し、Ｚ^３０１及びＺ^３０２は、置換アミノ基、水素原子、置換基を有していてもよいヒドロカルビル基、又は、置換基を有していてもよいヒドロカルビルオキシ基を表し、Ｚ^３０１及びＺ^３０２の少なくとも１つが置換アミノ基を有する基であるか、あるいは、Ｚ^３０１とＺ^３０２とが結合して、置換アミノ基を有する環構造をＺ^３０１とＺ^３０２とカルボニル炭素とで形成する基を表す。） The compound (G) is preferably a compound represented by the following formula (33).

(In the formula, E represents an oxygen atom or a sulfur atom, and Z ³⁰¹ and Z ³⁰² have a substituted amino group, a hydrogen atom, a hydrocarbyl group which may have a substituent, or a substituent. represents also good hydrocarbyloxy ^group, or a group having at least one substituted amino group of ^{Z 301} and ^{Z 302, or} by bonding with ^{Z 301} and ^{Z 302,} a ring structure having a substituted amino group ^{Z 301} And represents a group formed by Z ³⁰² and a carbonyl carbon.)

（式中、ｐ^３は０又は１であり、Ｔ^３０１は炭素原子数１〜１０のヒドロカルビレン基、下記式（３３−Ｔａ）で表される基、又は、下記式（３３−Ｔｂ）で表される基を表し、Ａ^３０３は置換アミノ基を表し、式（３３）のＺ^３０２がヒドロカルビル基である場合、Ｚ^３０１のＡ^３０３とＺ^３０２のヒドロカルビル基とは結合していてもよく、式（３３）のＺ^３０２が式（３３−Ｚ）で表される基である場合、Ｚ^３０１のＡ^３０３とＺ^３０２のＡ^３０３とは結合していてもよい。）

（式中、Ｒ^３３１は炭素原子数１〜１０のヒドロカルビレン基を表し、Ｒ^３３１がＡ^３０３と結合する。）

（式中、Ｒ^３３２は炭素原子数１〜１０のヒドロカルビレン基を表し、Ｒ^３３３は水素原子又は炭素原子数１〜１０のヒドロカルビル基を表し、Ｒ^３３２がＡ^３０３と結合する。） In the formula (33), E is an oxygen atom, Z ³⁰¹ is a group represented by the following formula (33-Z), and Z ³⁰² is a hydrocarbyl group or a group represented by the following formula (33-Z). It is preferable that

(In the formula, p ³ is 0 or 1, and T ³⁰¹ is a hydrocarbylene group having 1 to 10 carbon atoms, a group represented by the following formula (33-Ta), or a following formula (33-Tb). A ³⁰³ represents a substituted amino group, and when Z ^{302 in} Formula (33) is a hydrocarbyl group, A ³⁰³ in Z ³⁰¹ and the hydrocarbyl group in Z ³⁰² may be bonded to each other. when ^{Z 302} of formula (33) is a group represented by the formula ^(33-Z), may be bonded to the ^{a 303} of the ^{a 303} and ^{Z 302} for ^{Z 301.)}

^{(Wherein, R 331} represents a hydrocarbylene group having 1 to 10 carbon ^{atoms, R 331} is bonded to ^{A 303.)}

(Wherein R ³³² represents a hydrocarbylene group having 1 to 10 carbon atoms, R ³³³ represents a hydrogen atom or a hydrocarbyl group having 1 to 10 carbon atoms, and R ³³² is bonded to A ^303. )

（式中、Ｒ^３１１は水素原子又はヒドロカルビル基を表し、ｎ^３は０又は１であり、Ｒ^３１２はヒドロカルビレン基を表す。）

（式中、Ｘ^３０１、Ｘ^３０２及びＸ^３０３は、それぞれ独立に、置換アミノ基、又は、置換基を有していてもよいヒドロカルビル基を表し、Ｘ^３０１、Ｘ^３０２及びＸ^３０３の少なくとも１つが置換アミノ基である。） The group represented by V ³⁰¹ in the formula (31) is a group represented by the following formula (31-V1), and the group represented by S ³⁰¹ in the formula (31) is represented by the following formula (31-S It is preferable that it is group represented by.

(Wherein R ³¹¹ represents a hydrogen atom or a hydrocarbyl group, n ³ represents 0 or 1, and R ³¹² represents a hydrocarbylene group.)

( ^Wherein X ³⁰¹ , X ³⁰² and X ³⁰³ each independently represent a substituted amino group or a hydrocarbyl group which may have a substituent, wherein at least one of X ³⁰¹ , X ³⁰² and X ³⁰³ is A substituted amino group.)

In Formula (31-V1), R ³¹¹ is preferably a hydrogen atom, and n ³ is preferably 0.

The vinyl bond content of the conjugated diene polymer (C) is preferably 20 mol% or more and 70 mol% or less, with the content of the structural unit based on the conjugated diene being 100 mol%.

（式中、ｍ^４は１〜３の整数を表し、Ｒ^４０１は重合性炭素−炭素二重結合を有するヒドロカルビル基を表し、Ｒ^４０２はヒドロカルビレン基を表し、Ｒ^４０２が複数ある場合、複数あるＲ^４０２は同一でも異なっていてもよく、Ａ^４０１は置換アミノ基を表し、Ａ^４０１が複数ある場合、複数あるＡ^４０１は同一でも異なっていてもよく、Ｒ^４０３はヒドロカルビル基、置換ヒドロカルビル基又は置換アミノ基を表し、Ｒ^４０３が複数ある場合、複数あるＲ^４０３は同一でも異なっていてもよい。） 4th this invention contains a rubber component, a silica, and electroconductive carbon black, and is based on the structural unit based on a conjugated diene, and the compound represented by following formula (41) in 100 mass% of said rubber components. The content of the conjugated diene polymer (D) having a structural unit is 5% by mass or more, and the content of the silica is 5 to 150 parts by mass with respect to 100 parts by mass of the rubber component. The conductive carbon black It is related with the rubber composition for treads whose content is 3-30 mass parts.

(In the formula, m ⁴ represents an integer of 1 to 3, R ⁴⁰¹ represents a hydrocarbyl group having a polymerizable carbon-carbon double bond, R ⁴⁰² represents a hydrocarbylene group, and when there are a plurality of R ⁴⁰² , plural ^{R 402} may be the same or ^{different, a 401} represents a substituted amino ^{group, if a 401} there is a plurality, a plurality of ^{a 401} may be the same or ^{different, R 403} is a hydrocarbyl group, substituted hydrocarbyl represents a group or a substituted amino group, if R ⁴⁰³ is more, plural R ⁴⁰³ may be the same or different.)

（式中、ｎ^４は０〜２の整数を表し、Ｒ^４２１、Ｒ^４２２及びＲ^４２３は、それぞれ独立に、水素原子又はヒドロカルビル基を表す。） In the formula (41), it is preferable that m ⁴ is 1, R ⁴⁰¹ is a group represented by the following formula (42), R ⁴⁰² is an alkylene group, and R ⁴⁰³ is an alkyl group.

(In the formula, n ⁴ represents an integer of 0 to 2, and R ⁴²¹ , R ⁴²² and R ⁴²³ each independently represents a hydrogen atom or a hydrocarbyl group.)

In the formula (42), R ⁴²¹ , R ⁴²² and R ⁴²³ are preferably hydrogen atoms, and n ⁴ is preferably 0.

It is preferable that the molecular weight distribution represented by the ratio (Mw / Mn) of the weight average molecular weight (Mw) and the number average molecular weight (Mn) of the conjugated diene polymer (D) is 1 to 3.

The vinyl bond content of the conjugated diene polymer (D) is preferably 20 mol% or more and 70 mol% or less, with the content of the structural unit based on diene being 100 mol%.

（式中、ｍ^５は１又は２を表し、ｎ^５は１又は２を表し、ｍ^５＋ｎ^５は２又は３であり、Ｒ^５０１は重合性炭素−炭素二重結合を有するヒドロカルビル基を表し、Ｒ^５０２はヒドロカルビル基を表し、Ｒ^５０２が複数ある場合、複数あるＲ^５０２は同一でも異なっていてもよく、Ｒ^５０３は含酸素置換基を有していてもよいアリール基を表し、Ｒ^５０３が複数ある場合、複数あるＲ^５０３は同一でも異なっていてもよく、Ｒ^５０４はアルキル基、又は置換アミノ基を表す。） 5th this invention contains a rubber component, a silica, and electroconductive carbon black, and is based on the structural unit based on a conjugated diene, and the compound represented by following formula (51) in 100 mass% of said rubber components. The content of the conjugated diene polymer (E) having a structural unit is 5% by mass or more, and the content of the silica is 5 to 150 parts by mass with respect to 100 parts by mass of the rubber component. The conductive carbon black It is related with the rubber composition for treads whose content is 3-30 mass parts.

(In the formula, m ⁵ represents 1 or 2, n ⁵ represents 1 or 2, m ⁵ + n ⁵ represents 2 or 3, and R ⁵⁰¹ represents a hydrocarbyl group having a polymerizable carbon-carbon double bond. , ^{R 502} represents a hydrocarbyl ^{group, if R 502} is more, a plurality of ^{R 502} may be the same or ^{different, R 503} represents an aryl group which may have an oxygen-containing ^{substituent, R 503} When there are a plurality of R ^503s , the plurality of R ^503s may be the same or different, and R ⁵⁰⁴ represents an alkyl group or a substituted amino group.)

（式中、ｐ^５は０又は１であり、Ｒ^５０５は水素原子又はヒドロカルビル基を表し、Ｔ^５０１はヒドロカルビレン基を表す。） In the formula (51), m ⁵ + n ⁵ is 3, R ⁵⁰¹ is a group represented by the following formula (52), R ⁵⁰² is a tertiary alkyl group, and R ⁵⁰³ has an alkyl group. It is preferably an optionally substituted phenyl group.

(In the formula, p ⁵ is 0 or 1, R ⁵⁰⁵ represents a hydrogen atom or a hydrocarbyl group, and T ⁵⁰¹ represents a hydrocarbylene group.)

In the formula (51), R ⁵⁰¹ is preferably a vinyl group.

It is preferable that the molecular weight distribution represented by the ratio (Mw / Mn) of the weight average molecular weight (Mw) and the number average molecular weight (Mn) of the conjugated diene polymer (E) is 1.0 to 1.5. .

The vinyl bond content of the conjugated diene polymer (E) is preferably 20 mol% or more and 70 mol% or less, with the content of structural units based on diene being 100 mol%.

（式中、ｌ^６〜ｎ^６は、独立に、１〜８の整数を表す。） The sixth aspect of the present invention contains a rubber component, silica, and conductive carbon black. In 100% by mass of the rubber component, in a hydrocarbon solvent, in the presence of a Lewis basic compound, A compound represented by the following formula (61) is reacted with an active conjugated diene polymer having an alkali metal terminal obtained by polymerizing a conjugated diene monomer and an aromatic vinyl monomer using an alkali metal catalyst. The content of the conjugated diene polymer (F) is 5% by mass or more, the content of the silica is 5 to 150 parts by mass, and the content of the conductive carbon black is 100 parts by mass of the rubber component. It is related with the rubber composition for treads whose is 3-30 mass parts.

(Wherein l ^{6 to} n ⁶ independently represent an integer of 1 to 8)

It is preferable that the molecular weight distribution represented by ratio (Mw / Mn) of the weight average molecular weight (Mw) and the number average molecular weight (Mn) of the conjugated diene polymer (F) is 1.0 to 1.5. .

The vinyl bond content of the conjugated diene polymer (F) is preferably 10 to 70 mol%, where the content of conjugated diene units is 100 mol%.

（式中、Ｒ^７１１は水素原子又は炭素原子数１〜５のヒドロカルビル基を表し、ｍ^７は０又は１であり、Ｒ^７１２はヒドロカルビレン基を表し、Ｒ^７１３及びＲ^７１４は、それぞれ、ヒドロカルビル基、又は、トリヒドロカルビルシリル基、あるいは、Ｒ^７１３とＲ^７１４とが結合して、窒素原子及び／又は酸素原子を有していてもよいヒドロカルビレン基、又は、Ｒ^７１３とＲ^７１４は１つの基であって、窒素原子に二重結合で結合する基を表す。）

（式中、ｎ^７は１〜１０の整数を表し、Ｒ^７２１、Ｒ^７２２及びＲ^７２３は、それぞれ、ヒドロカルビル基又はヒドロカルビルオキシ基を表し、Ｒ^７２１、Ｒ^７２２及びＲ^７２３の少なくとも１つがヒドロカルビルオキシ基であり、Ｒ^７２４及びＲ^７２５は、それぞれ、水素原子、窒素原子及び／又は酸素原子を有していてもよいヒドロカルビル基、あるいは、Ｒ^７２４とＲ^７２５とが結合して、窒素原子及び／又は酸素原子を有していてもよいヒドロカルビレン基、又は、Ｒ^７２４とＲ^７２５は１つの基であって、窒素原子に二重結合で結合する基を表す。） 7th this invention contains a rubber component, a silica, and electroconductive carbon black, and is based on the structural unit based on a conjugated diene, and the compound represented by following formula (71) in 100 mass% of said rubber components. Content of conjugated diene polymer (G) obtained by making the compound represented by following formula (72) react with one end of the conjugated diene polymer which has a structural unit is 5 mass% or more, The said rubber component It is related with the rubber composition for treads whose content of the said silica is 5-150 mass parts and whose content of the said conductive carbon black is 3-30 mass parts with respect to 100 mass parts.

Wherein R ⁷¹¹ represents a hydrogen atom or a hydrocarbyl group having 1 to 5 carbon atoms, m ⁷ is 0 or 1, R ⁷¹² represents a hydrocarbylene group, and R ⁷¹³ and R ⁷¹⁴ are respectively Hydrocarbyl group, trihydrocarbyl silyl group, R ⁷¹³ and R ⁷¹⁴ are bonded to each other, and hydrocarbylene group optionally having nitrogen and / or oxygen atoms, or R ⁷¹³ and R ⁷¹⁴ are 1 group representing a group bonded to a nitrogen atom with a double bond.)

(In the formula, n ⁷ represents an integer of 1 to 10, R ⁷²¹ , R ⁷²² and R ⁷²³ each represents a hydrocarbyl group or a hydrocarbyloxy group, and at least one of R ⁷²¹ , R ⁷²² and R ⁷²³ is hydrocarbyloxy. Each of R ⁷²⁴ and R ⁷²⁵ is a hydrogen carbyl group which may have a hydrogen atom, a nitrogen atom and / or an oxygen atom, or R ⁷²⁴ and R ⁷²⁵ are bonded to each other to form a nitrogen atom and / Or a hydrocarbylene group which may have an oxygen atom, or R ⁷²⁴ and R ⁷²⁵ represent one group which represents a group bonded to a nitrogen atom with a double bond.

（式中、（ＣＨ_２）_ｐ７はベンゼン環上の置換基であり、ｐ^７は０〜５の整数を表し、ｐ^７が１〜５の整数である場合、（ＣＨ_２）_ｐ７が式（７１）の窒素原子と結合する。） In the formula (71), R ⁷¹¹ is preferably a hydrogen atom, m ⁷ is 1, and R ⁷¹² is preferably a group represented by the following formula (73).

_{(Wherein, (CH 2) p7} is a substituent on the benzene ring, ^{p 7} represents an integer of 0 to 5, when ^{p 7} is an integer of 1 to _{5, (CH 2) p7} Formula ( 71) to the nitrogen atom.)

In the formula (72), R ⁷²¹ , R ⁷²² and R ⁷²³ are preferably hydrocarbyloxy groups, and R ⁷²⁴ and R ⁷²⁵ are preferably hydrocarbyl groups.

The content of monomer units based on the compound represented by the formula (71) is 0.01 to 20% by mass, where the total amount of monomer units in the conjugated diene polymer (G) is 100% by mass. It is preferable that

The vinyl bond content of the conjugated diene polymer (G) is preferably 20 mol% or more and 70 mol% or less, where the content of monomer units based on the conjugated diene is 100 mol%.

（式中、Ｒ^８１１は水素原子又はヒドロカルビル基を表し、ｍ^８は０又は１であり、Ｒ^８１２はヒドロカルビレン基を表し、Ｔ^８０１は含窒素複素環基を表す。）

（式中、ｎ^８は１〜１０の整数を表し、Ｒ^８２１、Ｒ^８２２及びＲ^８２３は、それぞれ、ヒドロカルビル基又はヒドロカルビルオキシ基を表し、Ｒ^８２１、Ｒ^８２２及びＲ^８２３の少なくとも１つがヒドロカルビルオキシ基であり、Ｒ^８２４及びＲ^８２５は、それぞれ、水素原子、窒素原子及び／又は酸素原子を有していてもよいヒドロカルビル基、あるいは、Ｒ^８２４とＲ^８２５とが結合して、窒素原子及び／又は酸素原子を有していてもよいヒドロカルビレン基、又は、Ｒ^８２４とＲ^８２５は１つの基であって、窒素原子に二重結合で結合する基を表す。） The eighth present invention contains a rubber component, silica, and conductive carbon black, and is based on a structural unit based on a conjugated diene and a compound represented by the following formula (81) in 100% by mass of the rubber component. The content of the monomer unit based on the compound represented by the following formula (81) obtained by reacting the compound represented by the following formula (82) with one end of the conjugated diene polymer having a structural unit, The total amount of monomer units in the conjugated diene polymer is 100% by mass, and the content of the conjugated diene polymer (H) that is 0.01 to 20% by mass is 5% by mass or more, and the rubber component It is related with the rubber composition for treads whose content of the said silica is 5-150 mass parts and whose content of the said conductive carbon black is 3-30 mass parts with respect to 100 mass parts.

(In the formula, R ⁸¹¹ represents a hydrogen atom or a hydrocarbyl group, m ⁸ is 0 or 1, R ⁸¹² represents a hydrocarbylene group, and T ⁸⁰¹ represents a nitrogen-containing heterocyclic group.)

(In the formula, n ⁸ represents an integer of 1 to 10, R ⁸²¹ , R ⁸²² and R ⁸²³ each represents a hydrocarbyl group or a hydrocarbyloxy group, and at least one of R ⁸²¹ , R ⁸²² and R ⁸²³ is hydrocarbyloxy. Each of R ⁸²⁴ and R ⁸²⁵ is a hydrocarbyl group optionally having a hydrogen atom, a nitrogen atom and / or an oxygen atom, or a combination of R ⁸²⁴ and R ⁸²⁵ to form a nitrogen atom and / Or a hydrocarbylene group which may have an oxygen atom, or R ⁸²⁴ and R ⁸²⁵ are one group and represent a group bonded to a nitrogen atom by a double bond.)

In the formula (82), it is preferable that R ⁸²¹ , R ⁸²² and R ⁸²³ are hydrocarbyloxy groups, and R ⁸²⁴ and R ⁸²⁵ are hydrocarbyl groups.

In the formula (81), it is preferable that R ⁸¹¹ is a hydrogen atom and T ⁸⁰¹ is a pyridyl group.

The vinyl bond content of the conjugated diene polymer (H) is preferably 20 mol% or more and 70 mol% or less, where the content of monomer units based on the conjugated diene is 100 mol%.

The conductive carbon black is preferably a nitrogen adsorption specific surface area of 40 to 80 m ² / g, a dibutyl phthalate absorption is 110~230cm ³ / 100g.

The present invention also relates to a pneumatic tire produced using the rubber composition.

According to the present invention, since it is a rubber composition containing a predetermined amount of at least one of the conjugated diene polymers (A) to (H), silica, and conductive carbon black, low fuel consumption, wet grip A pneumatic tire with improved performance and wear resistance in a well-balanced manner can be provided.

（式中、Ｒ^１１１は水素原子又はヒドロカルビル基を表し、ｍ^１は０又は１であり、Ｒ^１１２はヒドロカルビレン基を表し、Ｘ^１０１、Ｘ^１０２及びＸ^１０３は、それぞれ独立に、置換アミノ基、又は、置換基を有していてもよいヒドロカルビル基を表し、Ｘ^１０１、Ｘ^１０２及びＸ^１０３の少なくとも１つが置換アミノ基である。）

（式中、Ｒ^１２１は水素原子又はヒドロカルビル基を表し、ｎ^１は０又は１であり、Ｒ^１２２はヒドロカルビレン基を表し、Ａ^１０１は置換アミノ基、又は、含窒素複素環基を表す。） The conjugated diene polymer (A) according to the first aspect of the present invention includes a monomer unit based on a conjugated diene, a monomer unit based on a compound represented by the following formula (11), and a formula (12) below. Monomer units based on the compounds represented.

(Wherein R ¹¹¹ represents a hydrogen atom or a hydrocarbyl group, m ¹ is 0 or 1, R ¹¹² represents a hydrocarbylene group, and X ¹⁰¹ , X ¹⁰² and X ¹⁰³ are each independently substituted amino A hydrocarbyl group which may have a group or a substituent, and at least one of X ¹⁰¹ , X ¹⁰² and X ¹⁰³ is a substituted amino group.)

(In the formula, R ¹²¹ represents a hydrogen atom or a hydrocarbyl group, n ¹ is 0 or 1, R ¹²² represents a hydrocarbylene group, and A ¹⁰¹ represents a substituted amino group or a nitrogen-containing heterocyclic group. .)

As used herein, a hydrocarbyl group represents a hydrocarbon residue. The hydrocarbylene group represents a divalent hydrocarbon residue. The nitrogen-containing heterocyclic group represents a group obtained by removing one hydrogen atom from the carbon atom of a heterocyclic ring of a compound having a nitrogen-containing heterocyclic ring. The nitrogen-containing heterocyclic ring is a heterocyclic group having a nitrogen atom as a hetero atom constituting the ring. Represents a ring.

Examples of the conjugated diene include 1,3-butadiene, isoprene, 1,3-pentadiene, 2,3-dimethyl-1,3-butadiene, 1,3-hexadiene and the like, and one or more of these are used. . The conjugated diene is preferably 1,3-butadiene or isoprene.

R ^{111 in the} formula (11) represents a hydrogen atom or a hydrocarbyl group.

^Examples of the hydrocarbyl group for R ¹¹¹ include an alkyl group and an alkenyl group.
Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, and a tert-butyl group, and a methyl group is preferable. Examples of the alkenyl group include a vinyl group, an allyl group, a 1-propenyl group, and a 1-methylethenyl group, and a vinyl group is preferable.

R ¹¹¹ is preferably a hydrogen atom, a methyl group, or a vinyl group.

^Examples of the hydrocarbylene group for R ¹¹² include an alkylene group, an arylene group, and a group in which an arylene group and an alkylene group are bonded.

Examples of the alkylene group include a methylene group, an ethylene group, and a trimethylene group. Preferably, it is a methylene group or an ethylene group.

Examples of the arylene group include a phenylene group, a naphthylene group, and a biphenylene group. A phenylene group is preferred.

Examples of the group in which an arylene group and an alkylene group are bonded include a group in which a phenylene group and an alkylene group are bonded, a group in which a naphthylene group and an alkylene group are bonded, and a group in which a biphenylene group and an alkylene group are bonded. .

Moreover, it is preferable that the carbon atom of the alkylene group couple | bonds the group which the arylene group and the alkylene group couple | bonded with the silicon atom of Formula (11).

（式中、ｑ^１は、１〜１０の整数を表す。） In a group in which a phenylene group and an alkylene group are bonded (phenylene-alkylene group), depending on the position of the carbon atom on the benzene ring from which a hydrogen atom is removed and the phenylene group to which the alkylene group is bonded, a para-phenylene-alkylene group ( For example, a group represented by the following formula (11a)), a meta-phenylene-alkylene group (for example, a group represented by the following formula (11b)), an ortho-phenylene-alkylene group (for example, the following formula (11c) )))).

(Wherein, ^{q 1} represents an integer of 1 to 10.)

The group in which an arylene group and an alkylene group are bonded is preferably a group in which a phenylene group and an alkylene group are bonded, and more preferably a group represented by the above formula (11a) or the above formula (11b). And more preferably a para-phenylene-methylene group (a group represented by the formula (11a) in which q ¹ = 1) and a meta-phenylene-methylene group (a formula in which q ¹ = 1 ( Group represented by formula (11b)), para-phenylene-ethylene group (group represented by formula (11a) where q ¹ = 2), meta-phenylene-ethylene group (formula (11b) where q ¹ = 2) A group represented by:

When R ¹¹¹ is a hydrogen atom or a methyl group and m ¹ is 1, R ¹¹² is preferably a group in which an arylene group and an alkylene group are bonded or an arylene group, more preferably a phenylene group and an alkylene. And a phenylene group, more preferably a phenylene group.

When R ¹¹¹ is a vinyl group and m ¹ is 1, R ¹¹² is preferably an alkylene group, more preferably a methylene group or an ethylene group.

In Formula (11), R ¹¹¹ is preferably a hydrogen atom and m ¹ is 0.

The hydrocarbyl group which may have a substituent of X ¹⁰¹ , X ¹⁰² and X ¹⁰³ is a hydrocarbyl group which may have at least one selected from the group consisting of an oxygen atom, a nitrogen atom and a silicon atom Can give.

Examples of the hydrocarbyl group of X ¹⁰¹ , X ¹⁰² and X ¹⁰³ include an alkyl group, an alkenyl group, an alkynyl group, an aryl group and an aralkyl group. Examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, and tert-butyl group. Examples of the alkenyl group include a vinyl group, an allyl group, a 1-propenyl group, and a 1-methylethenyl group. Examples of the alkynyl group include an ethynyl group and a propargyl group. Examples of the aryl group include a phenyl group, a tolyl group, and a xylyl group. Examples of the aralkyl group include a benzyl group. The hydrocarbyl group is preferably an alkyl group.

Examples of the hydrocarbyl group having an oxygen atom of X ¹⁰¹ , X ¹⁰² and X ¹⁰³ include alkoxyalkyl groups such as a methoxymethyl group, a methoxyethyl group, an ethoxymethyl group and an ethoxyethyl group.

Examples of the hydrocarbyl group having a nitrogen atom of X ¹⁰¹ , X ¹⁰² and X ¹⁰³ include dialkylaminoalkyl groups such as dimethylaminomethyl group, dimethylaminoethyl group, diethylaminomethyl group and diethylaminoethyl group.

Examples of the hydrocarbyl group having a silicon atom of X ¹⁰¹ , X ¹⁰² and X ¹⁰³ include trialkylsilylalkyl groups such as trimethylsilylmethyl group, trimethylsilylethyl group, triethylsilylmethyl group and triethylsilylethyl group.

The number of carbon atoms of the hydrocarbyl group which may have a substituent of X ¹⁰¹ , X ¹⁰² and X ¹⁰³ is preferably 1 to 10, more preferably 1 to 4.

The hydrocarbyl group which may have a substituent of X ¹⁰¹ , X ¹⁰² and X ¹⁰³ is preferably an alkyl group or an alkoxyalkyl group. The alkyl group is preferably an alkyl group having 1 to 4 carbon atoms, more preferably a methyl group or an ethyl group. The alkoxyalkyl group is preferably an alkoxyalkyl group having 2 to 4 carbon atoms.

（式中、Ｒ^１１３及びＲ^１１４は、それぞれ、ヒドロカルビル基、又は、トリヒドロカルビルシリル基、あるいは、Ｒ^１１３とＲ^１１４とが結合して、窒素原子及び／又は酸素原子をヘテロ原子として有していてもよいヒドロカルビレン基、又は、Ｒ^１１３とＲ^１１４は１つの基であって、窒素原子に二重結合で結合する基を表す。） The substituted amino group for X ¹⁰¹ , X ¹⁰² and X ¹⁰³ is preferably a group represented by the following formula (11-X).

(Wherein R ¹¹³ and R ¹¹⁴ each have a hydrocarbyl group, a trihydrocarbyl silyl group, or R ¹¹³ and R ¹¹⁴ bonded to each other and have a nitrogen atom and / or an oxygen atom as a hetero atom. The hydrocarbylene group which may be substituted, or R ¹¹³ and R ¹¹⁴ are one group and represent a group bonded to the nitrogen atom by a double bond.)

^Examples of the hydrocarbyl group of R ¹¹³ and R ¹¹⁴ include an alkyl group, an alkenyl group, an alkynyl group, an aryl group, and an aralkyl group. Examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, and tert-butyl group. Examples of the alkenyl group include a vinyl group, an allyl group, a 1-propenyl group, and a 1-methylethenyl group. Examples of the alkynyl group include an ethynyl group and a propargyl group. Examples of the aryl group include a phenyl group, a tolyl group, and a xylyl group. Examples of the aralkyl group include a benzyl group.

The number of carbon atoms of the hydrocarbyl group of R ¹¹³ and R ¹¹⁴ is preferably 1 to 10, more preferably 1 to 4, and still more preferably 1 to 2.

The hydrocarbyl group of R ¹¹³ and R ¹¹⁴ is preferably an alkyl group, more preferably a linear alkyl group.

The trihydrocarbyl silyl group R ¹¹³ and R ^114, may be mentioned trimethylsilyl group, triethylsilyl group, triisopropylsilyl group, a trialkylsilyl group such as tert- butyldimethylsilyl group.

The trihydrocarbyl silyl group R ¹¹³ and R ^114, preferably a trialkylsilyl group having a carbon number of 3 to 9, more preferably an alkyl group bonded to the silicon atoms of 1 to 3 carbon atoms A trialkylsilyl group which is an alkyl group, and more preferably a trimethylsilyl group.

The hydrocarbylene group optionally having a nitrogen atom and / or an oxygen atom to which R ¹¹³ and R ¹¹⁴ are bonded as a hetero atom includes a hydrocarbylene group, a hydrocarbylene group having a nitrogen atom, and an oxygen atom. And hydrocarbylene groups. Examples of the hydrocarbylene group include an alkylene group such as an ethylene group, a trimethylene group, a tetramethylene group, a pentamethylene group, and a hexamethylene group. As the hydrocarbylene group having a nitrogen atom, a group represented by —CH ₂ CH ₂ —NH—CH ₂ —, a group represented by —CH ₂ CH ₂ —N═CH—, —CH═CH—N A group represented by ═CH— and a group represented by —CH ₂ CH ₂ —NH—CH ₂ CH ₂ — can be exemplified. Examples of the hydrocarbylene group having an oxygen atom include a group represented by —CH ₂ CH ₂ —O—CH ₂ CH ₂ —.

The number of carbon atoms of the hydrocarbylene group which may have a nitrogen atom and / or oxygen atom to which R ¹¹³ and R ¹¹⁴ are bonded as a hetero atom is preferably 2 to 20, more preferably 2 to 7. Yes, more preferably 4-6.

The hydrocarbylene group which may have a nitrogen atom and / or oxygen atom to which R ¹¹³ and R ¹¹⁴ are bonded as a hetero atom is preferably a hydrocarbylene group, more preferably an alkylene group, A polymethylene group is preferred.

Examples of one group in which R ¹¹³ and R ¹¹⁴ are bonded to the nitrogen atom by a double bond include ethylidene group, propylidene group, butylidene group, 1-methylethylidene group, 1-methylpropylidene group, 1,3-dimethylbutylidene And hydrocarbylidene groups such as groups.

The number of carbon atoms of one group in which R ¹¹³ and R ¹¹⁴ are bonded to the nitrogen atom with a double bond is preferably 2 to 20, and more preferably 2 to 6.

R ¹¹³ and R ¹¹⁴ are preferably an alkyl group, a trialkylsilyl group, an alkylene group in which R ¹¹³ and R ¹¹⁴ are bonded, and more preferably an alkyl group.

Examples of the group represented by the formula (11-X) include an acyclic amino group and a cyclic amino group.

Examples of the acyclic amino group include a dialkylamino group and a bis (trialkylsilyl) amino group. Dialkylamino groups include dimethylamino, diethylamino, di (n-propyl) amino, di (isopropyl) amino, di (n-butyl) amino, di (sec-butyl) amino, di (tert -Butyl) amino group and ethylmethylamino group can be mentioned. Examples of the bis (trialkylsilyl) amino group include a bis (trimethylsilyl) amino group and a bis (t-butyldimethylsilyl) amino group.

Examples of the acyclic amino group include an ethylideneamino group, a 1-methylpropylideneamino group, a 1,3-dimethylbutylideneamino group, a 1-methylethylideneamino group, and a 4-N, N-dimethylaminobenzylideneamino group. Can do.

Examples of the cyclic amino group include 1-aziridinyl group, 1-azetidinyl group, 1-pyrrolidinyl group, 1-piperidinyl group, 1-hexamethyleneimino group, 1-heptamethyleneimino group, 1-octamethyleneimino group, 1-decamidine group. Examples thereof include 1-polymethyleneimino groups such as a methyleneimino group and 1-dodecamethyleneimino group. Moreover, 1-pyrrolyl group, 1-pyrazolidinyl group, 1-imidazolidinyl group, 1-pyrazolyl group, 1-imidazolyl group, 4,5-dihydro-1-imidazolyl group, 1-piperazinyl group and morpholino group are exemplified.

The group represented by the formula (11-X) is preferably an acyclic amino group, and more preferably a dialkylamino group. The dialkylamino group is preferably a dimethylamino group, a diethylamino group, a di (n-propyl) amino group, or a di (n-butyl) amino group, and more preferably a dimethylamino group or a diethylamino group.

In formula (11), at least one of X ¹⁰¹ , X ¹⁰² and X ¹⁰³ is a substituted amino group, preferably two or more of X ¹⁰¹ , X ¹⁰² and X ¹⁰³ are substituted amino groups, more preferably, Two of X ¹⁰¹ , X ¹⁰² and X ¹⁰³ are substituted amino groups.

Examples of the compound represented by the formula (11) include the following compounds as compounds in which R ¹¹¹ is a hydrogen atom and one of X ¹⁰¹ , X ¹⁰² and X ¹⁰³ is a dialkylamino group.

Compound in which m ¹ is 0:
(Dimethylamino) dimethylvinylsilane,
(Diethylamino) dimethylvinylsilane,
(Di-n-propylamino) dimethylvinylsilane,
(Di-n-butylamino) dimethylvinylsilane,
(Dimethylamino) diethylvinylsilane,
(Diethylamino) diethylvinylsilane,
(Di-n-propylamino) diethylvinylsilane,
(Di-n-butylamino) diethylvinylsilane.

Compound in which m ¹ is 1:
(Dimethylamino) dimethyl-4-vinylphenylsilane,
(Dimethylamino) dimethyl-3-vinylphenylsilane,
(Diethylamino) dimethyl-4-vinylphenylsilane,
(Diethylamino) dimethyl-3-vinylphenylsilane,
(Di-n-propylamino) dimethyl-4-vinylphenylsilane,
(Di-n-propylamino) dimethyl-3-vinylphenylsilane,
(Di-n-butylamino) dimethyl-4-vinylphenylsilane,
(Di-n-butylamino) dimethyl-3-vinylphenylsilane,
(Dimethylamino) diethyl-4-vinylphenylsilane,
(Dimethylamino) diethyl-3-vinylphenylsilane,
(Diethylamino) diethyl-4-vinylphenylsilane,
(Diethylamino) diethyl-3-vinylphenylsilane,
(Di-n-propylamino) diethyl-4-vinylphenylsilane,
(Di-n-propylamino) diethyl-3-vinylphenylsilane,
(Di-n-butylamino) diethyl-4-vinylphenylsilane,
(Di-n-butylamino) diethyl-3-vinylphenylsilane.

Examples of the compound represented by the formula (11) include the following compounds as compounds in which R ¹¹¹ is a hydrogen atom and two of X ¹⁰¹ , X ¹⁰² and X ¹⁰³ are dialkylamino groups.

Compound in which m ¹ is 0:
Bis (dimethylamino) methylvinylsilane,
Bis (diethylamino) methylvinylsilane,
Bis (di-n-propylamino) methylvinylsilane,
Bis (di-n-butylamino) methylvinylsilane,
Bis (dimethylamino) ethylvinylsilane,
Bis (diethylamino) ethylvinylsilane,
Bis (di-n-propylamino) ethylvinylsilane,
Bis (di-n-butylamino) ethylvinylsilane.

Compound in which m ¹ is 1:
Bis (dimethylamino) methyl-4-vinylphenylsilane,
Bis (dimethylamino) methyl-3-vinylphenylsilane,
Bis (diethylamino) methyl-4-vinylphenylsilane,
Bis (diethylamino) methyl-3-vinylphenylsilane,
Bis (di-n-propylamino) methyl-4-vinylphenylsilane,
Bis (di-n-propylamino) methyl-3-vinylphenylsilane,
Bis (di-n-butylamino) methyl-4-vinylphenylsilane,
Bis (di-n-butylamino) methyl-3-vinylphenylsilane,
Bis (dimethylamino) ethyl-4-vinylphenylsilane,
Bis (dimethylamino) ethyl-3-vinylphenylsilane,
Bis (diethylamino) ethyl-4-vinylphenylsilane,
Bis (diethylamino) ethyl-3-vinylphenylsilane,
Bis (di-n-propylamino) ethyl-4-vinylphenylsilane,
Bis (di-n-propylamino) ethyl-3-vinylphenylsilane,
Bis (di-n-butylamino) ethyl-4-vinylphenylsilane,
Bis (di-n-butylamino) ethyl-3-vinylphenylsilane.

Examples of the compound represented by formula (11) include the following compounds as compounds in which R ¹¹¹ is a methyl group and two of X ¹⁰¹ , X ¹⁰² and X ¹⁰³ are dialkylamino groups.

Compound in which m ¹ is 1:
Bis (dimethylamino) methyl-4-isopropenylphenylsilane,
Bis (dimethylamino) methyl-3-isopropenylphenylsilane,
Bis (diethylamino) methyl-4-isopropenylphenylsilane,
Bis (diethylamino) methyl-3-isopropenylphenylsilane,
Bis (di-n-propylamino) methyl-4-isopropenylphenylsilane,
Bis (di-n-propylamino) methyl-3-isopropenylphenylsilane,
Bis (di-n-butylamino) methyl-4-isopropenylphenylsilane,
Bis (di-n-butylamino) methyl-3-isopropenylphenylsilane,
Bis (dimethylamino) ethyl-4-isopropenylphenylsilane,
Bis (dimethylamino) ethyl-3-isopropenylphenylsilane,
Bis (diethylamino) ethyl-4-isopropenylphenylsilane,
Bis (diethylamino) ethyl-3-isopropenylphenylsilane,
Bis (di-n-propylamino) ethyl-4-isopropenylphenylsilane,
Bis (di-n-propylamino) ethyl-3-isopropenylphenylsilane,
Bis (di-n-butylamino) ethyl-4-isopropenylphenylsilane,
Bis (di-n-butylamino) ethyl-3-isopropenylphenylsilane.

Examples of the compound represented by formula (11) include the following compounds as compounds in which R ¹¹¹ is a vinyl group and two of X ¹⁰¹ , X ¹⁰² and X ¹⁰³ are dialkylamino groups.

Compound in which m ¹ is 0:
Bis (dimethylamino) methyl (1-methylene-2-propenyl) silane,
Bis (diethylamino) methyl (1-methylene-2-propenyl) silane,
Bis (di-n-propylamino) methyl (1-methylene-2-propenyl) silane,
Bis (di-n-butylamino) methyl (1-methylene-2-propenyl) silane,
Bis (dimethylamino) ethyl (1-methylene-2-propenyl) silane,
Bis (diethylamino) ethyl (1-methylene-2-propenyl) silane,
Bis (di-n-propylamino) ethyl (1-methylene-2-propenyl) silane,
Bis (di-n-butylamino) ethyl (1-methylene-2-propenyl) silane.

Examples of the compound represented by the formula (11) include the following compounds as compounds in which R ¹¹¹ is a hydrogen atom and three of X ¹⁰¹ , X ¹⁰² and X ¹⁰³ are dialkylamino groups.

Compound in which m ¹ is 0:
Tris (dimethylamino) vinylsilane,
Tris (diethylamino) vinylsilane,
Tris (di-n-propylamino) vinylsilane,
Tris (di-n-butylamino) vinylsilane.

Compound in which m ¹ is 1:
Tris (dimethylamino) -4-vinylphenylsilane,
Tris (dimethylamino) -3-vinylphenylsilane,
Tris (diethylamino) -4-vinylphenylsilane,
Tris (diethylamino) -3-vinylphenylsilane,
Tris (di-n-propylamino) -4-vinylphenylsilane,
Tris (di-n-propylamino) -3-vinylphenylsilane,
Tris (di-n-butylamino) -4-vinylphenylsilane,
Tris (di-n-butylamino) -3-vinylphenylsilane.

Examples of the compound represented by the formula (11) include the following compounds as compounds in which R ¹¹¹ is a methyl group and three of X ¹⁰¹ , X ¹⁰² and X ¹⁰³ are dialkylamino groups.

Compound in which m ¹ is 1:
Tris (dimethylamino) -4-isopropenylphenylsilane,
Tris (dimethylamino) -3-isopropenylphenylsilane,
Tris (diethylamino) -4-isopropenylphenylsilane,
Tris (diethylamino) -3-isopropenylphenylsilane,
Tris (di-n-propylamino) -4-isopropenylphenylsilane,
Tris (di-n-propylamino) -3-isopropenylphenylsilane,
Tris (di-n-butylamino) -4-isopropenylphenylsilane,
Tris (di-n-butylamino) -3-isopropenylphenylsilane.

Examples of the compound represented by formula (11) include the following compounds as compounds in which R ¹¹¹ is a vinyl group and three of X ¹⁰¹ , X ¹⁰² and X ¹⁰³ are dialkylamino groups.

Compound in which m ¹ is 0:
Tris (dimethylamino) (1-methylene-2-propenyl) silane,
Tris (diethylamino) (1-methylene-2-propenyl) silane,
Tris (di-n-propylamino) (1-methylene-2-propenyl) silane,
Tris (di-n-butylamino) (1-methylene-2-propenyl) silane.

The compound represented by the formula (11) is preferably a compound in which two of X ¹⁰¹ , X ¹⁰² and X ¹⁰³ are dialkylamino groups, more preferably R ¹¹¹ is a hydrogen atom, m ¹ = 0. More preferably, it is a compound in which the remaining one of X ¹⁰¹ , X ¹⁰² and X ¹⁰³ is an alkyl group or an alkoxyalkyl group. Particularly preferably,
Bis (dimethylamino) methylvinylsilane,
Bis (diethylamino) methylvinylsilane,
Bis (di-n-propylamino) methylvinylsilane,
Bis (di-n-butylamino) methylvinylsilane,
Bis (dimethylamino) ethylvinylsilane,
Bis (diethylamino) ethylvinylsilane,
Bis (di-n-propylamino) ethylvinylsilane,
Bis (di-n-butylamino) ethylvinylsilane.

R ^{121 in the} above formula (12) represents a hydrogen atom or a hydrocarbyl group.

^Examples of the hydrocarbyl group of R ¹²¹ include an alkyl group and an alkenyl group.
Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, and a tert-butyl group, and a methyl group is preferable. Examples of the alkenyl group include a vinyl group, an allyl group, a 1-propenyl group, and a 1-methylethenyl group, and a vinyl group is preferable.

R ¹²¹ is preferably a hydrogen atom, a methyl group, or a vinyl group.

^Examples of the hydrocarbylene group for R ¹²² include an alkylene group, an arylene group, and a group in which an arylene group and an alkylene group are bonded.

Examples of the alkylene group include a methylene group, an ethylene group, and a trimethylene group. Preferably, it is a methylene group or an ethylene group.

Examples of the arylene group include a phenylene group, a naphthylene group, and a biphenylene group. A phenylene group is preferred.

Examples of the group in which an arylene group and an alkylene group are bonded include a group in which a phenylene group and an alkylene group are bonded, a group in which a naphthylene group and an alkylene group are bonded, and a group in which a biphenylene group and an alkylene group are bonded. A group in which a phenylene group and an alkylene group are bonded is preferable.

In the group in which the arylene group and the alkylene group are bonded, the carbon atom of the arylene group is preferably bonded to the carbon atom to which R ¹²¹ of the formula (12) is bonded.

（式中、ｓ^１は１〜１０の整数を表す。） In a group in which a phenylene group and an alkylene group are bonded (phenylene-alkylene group), depending on the position of the carbon atom on the benzene ring from which a hydrogen atom is removed and the phenylene group to which the alkylene group is bonded, a para-phenylene-alkylene group ( For example, a group represented by the following formula (12a)), a meta-phenylene-alkylene group (for example, a group represented by the following formula (12b)), an ortho-phenylene-alkylene group (for example, the following formula (12c )))).

(Wherein s ¹ represents an integer of ¹ to 10)

The group in which an arylene group and an alkylene group are bonded is preferably a group in which a phenylene group and an alkylene group are bonded, and more preferably a group represented by the above formula (12a) or the above formula (12b). And more preferably a para-phenylene-methylene group (a group represented by the formula (12a) in which s ¹ = 1) and a meta-phenylene-methylene group (a formula in which s ¹ = 1 ( Group represented by formula (12b)), para-phenylene-ethylene group (group represented by formula (12a) where s ¹ = 2), meta-phenylene-ethylene group (formula (12b) where s ¹ = 2) A group represented by:

（式中、ｒ^１は０〜５の整数を表し、ｒ^１が１から５の整数である場合、（ＣＨ_２）_ｒ１はベンゼン環上の置換基であり、（ＣＨ_２）_ｒ１がＡ^１０１と結合し、ｒ^１が０である場合、（ＣＨ_２）_ｒ１はベンゼン環とＡ^１０１との結合を表す。）

（式中、ｒ^１は０〜５の整数を表し、ｒ^１が１から５の整数である場合、（ＣＨ_２）_ｒ１がＡ^１０１と結合し、ｒ^１が０である場合、（ＣＨ_２）_ｒ１はベンゼン環とＡ^１０１との結合を表す。） When R ¹²¹ is a hydrogen atom or a methyl group, and n ¹ is 1, R ¹²² is preferably a group in which an arylene group and an alkylene group are bonded or an arylene group, more preferably a phenylene group and an alkylene. A group bonded to a group or a phenylene group, more preferably a group represented by the following formula (12-Y), particularly preferably a group represented by the following formula (12-Ya) or the following formula: It is a group represented by (12-Yb). Further, wherein ^{r 1} is 0-5, preferably 0-2.

(Wherein, ^{r 1} represents an integer of 0 to 5, when ^{r 1} is an integer of from 5 to _{1, (CH 2) r1} is a substituent on the benzene _{ring, (CH 2) r1} is ^{A 101} And when r ¹ is 0, (CH ₂ ) _r1 represents a bond between the benzene ring and A ^101. )

(Wherein, ^{r 1} represents an integer of 0 to 5, when ^{r 1} is an integer from 1 to _5, combined with _{(CH 2) r1} is ^{A 101,} if ^{r 1} is 0, (CH ₂ ) _R1 represents a bond between the benzene ring and A ^101. )

When R ¹²¹ is a vinyl group and n ¹ is 1, R ¹²² is preferably an alkylene group, more preferably a methylene group or an ethylene group.

A ¹⁰¹ represents a substituted amino group or a nitrogen-containing heterocyclic group.

（式中、Ｒ^１２３及びＲ^１２４は、それぞれ、ヒドロカルビル基、又は、トリヒドロカルビルシリル基、あるいは、Ｒ^１２３とＲ^１２４とが結合して、窒素原子及び／又は酸素原子をヘテロ原子として有していてもよいヒドロカルビレン基、又は、Ｒ^１２３とＲ^１２４は１つの基であって、窒素原子に二重結合で結合する基を表す。） The substituted amino group for A ¹⁰¹ is preferably a group represented by the following formula (12-X).

(Wherein R ¹²³ and R ¹²⁴ each have a hydrocarbyl group, a trihydrocarbyl silyl group, or R ¹²³ and R ¹²⁴ bonded to each other to have a nitrogen atom and / or an oxygen atom as a hetero atom. The hydrocarbylene group, or R ¹²³ and R ¹²⁴ may be one group and represents a group bonded to the nitrogen atom with a double bond.)

^Examples of the hydrocarbyl group of R ¹²³ and R ¹²⁴ include an alkyl group, an alkenyl group, an alkynyl group, an aryl group, and an aralkyl group. Examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, and tert-butyl group. Examples of the alkenyl group include a vinyl group, an allyl group, a 1-propenyl group, and a 1-methylethenyl group. Examples of the alkynyl group include an ethynyl group and a propargyl group. Examples of the aryl group include a phenyl group, a tolyl group, and a xylyl group. Examples of the aralkyl group include a benzyl group.

The number of carbon atoms of the hydrocarbyl group of R ¹²³ and R ¹²⁴ is preferably 1 to 10, more preferably 1 to 4, and still more preferably 1 to 2.

The hydrocarbyl group for R ¹²³ and R ¹²⁴ is preferably an alkyl group or an alkenyl group, more preferably an alkyl group, and still more preferably a linear alkyl group.

The trihydrocarbyl silyl group R ¹²³ and R ^124, may be mentioned trimethylsilyl group, triethylsilyl group, triisopropylsilyl group, a trialkylsilyl group such as tert- butyldimethylsilyl group.

The trihydrocarbyl silyl group R ¹²³ and R ^124, preferably a trialkylsilyl group having a carbon number of 3 to 9, more preferably an alkyl group bonded to the silicon atoms of 1 to 4 carbon atoms A trialkylsilyl group which is an alkyl group, and more preferably a trimethylsilyl group.

The hydrocarbylene group optionally having a nitrogen atom and / or oxygen atom to which R ¹²³ and R ¹²⁴ are bonded as a hetero atom includes a hydrocarbylene group, a hydrocarbylene group having a nitrogen atom, and an oxygen atom. And hydrocarbylene groups. Examples of the hydrocarbylene group include an alkylene group such as an ethylene group, a trimethylene group, a tetramethylene group, a pentamethylene group, and a hexamethylene group. As the hydrocarbylene group having a nitrogen atom, a group represented by —CH ₂ CH ₂ —NH—CH ₂ —, a group represented by —CH ₂ CH ₂ —N═CH—, —CH═CH—N A group represented by ═CH— and a group represented by —CH ₂ CH ₂ —NH—CH ₂ CH ₂ — can be exemplified. Examples of the hydrocarbylene group having an oxygen atom include a group represented by —CH ₂ CH ₂ —O—CH ₂ CH ₂ —.

The number of carbon atoms of the hydrocarbylene group which may have a nitrogen atom and / or an oxygen atom to which R ¹²³ and R ¹²⁴ are bonded as a hetero atom is preferably 2 to 20, more preferably 2 to 7. Yes, more preferably 4-6.

The hydrocarbylene group which may have a nitrogen atom and / or oxygen atom to which R ¹²³ and R ¹²⁴ are bonded as a hetero atom is preferably a hydrocarbylene group, more preferably an alkylene group, A polymethylene group is preferred.

Examples of one group in which R ¹²³ and R ¹²⁴ are bonded to the nitrogen atom by a double bond include ethylidene group, propylidene group, butylidene group, 1-methylethylidene group, 1-methylpropylidene group, 1,3-dimethylbutylidene And hydrocarbylidene groups such as groups.

The number of carbon atoms of one group in which R ¹²³ and R ¹²⁴ are bonded to the nitrogen atom with a double bond is preferably 2 to 20, and more preferably 2 to 6.

R ¹²³ and R ¹²⁴ are preferably a hydrocarbyl group, a trihydrocarbyl silyl group, or a hydrocarbylene group in which R ¹²³ and R ¹²⁴ are bonded.

Examples of the group represented by the formula (12-X) include an acyclic amino group and a cyclic amino group.

Examples of the acyclic amino group include a dialkylamino group and a bis (trialkylsilyl) amino group. Dialkylamino groups include dimethylamino, diethylamino, di (n-propyl) amino, di (isopropyl) amino, di (n-butyl) amino, di (sec-butyl) amino, di (tert -Butyl) amino group and ethylmethylamino group can be mentioned. Examples of the bis (trialkylsilyl) amino group include a bis (trimethylsilyl) amino group and a bis (tert-butyldimethylsilyl) amino group.

The acyclic amino group further includes an ethylideneamino group, a 1-methylpropylideneamino group, a 1,3-dimethylbutylideneamino group, a 1-methylethylideneamino group, and a 4-N, N-dimethylaminobenzylideneamino group. You can also give it.

Examples of the cyclic amino group include 1-aziridinyl group, 1-azetidinyl group, 1-pyrrolidinyl group, 1-piperidinyl group, 1-hexamethyleneimino group, 1-imidazolyl group, 4,5-dihydro-1-imidazolyl group, 1 Examples include -pyrrolyl group, 1-pyrazolyl group, 1-imidazolidinyl group, 1-piperazinyl group, and morpholino group.

The group represented by the formula (12-X) is preferably a group in which R ¹²³ and R ¹²⁴ are hydrocarbyl groups, a group in which R ¹²³ and R ¹²⁴ are trihydrocarbylsilyl groups, and R ¹²³ and R ¹²⁴ are bonded. Group which is a hydrocarbylene group. More preferably, R ¹²³ and R ¹²⁴ are a group that is a linear alkyl group, R ¹²³ and R ¹²⁴ are a group that is a trialkylsilyl group, and a group that is a polymethylene group to which R ¹²³ and R ¹²⁴ are bonded.

As the group represented by the formula (12-X), more preferably, a dimethylamino group, a diethylamino group, a di (n-propyl) amino group, a di (n-butyl) amino group, a bis (trimethylsilyl) amino group, A bis (tert-butyldimethylsilyl) amino group, a 1-pyrrolidinyl group, a 1-piperidinyl group, and a 1-hexamethyleneimino group, particularly preferably a 1-pyrrolidinyl group.

^Examples of the nitrogen-containing heterocyclic group represented by A ¹⁰¹ include a nitrogen-containing aliphatic heterocyclic group and a nitrogen-containing aromatic heterocyclic group. In the present specification, a nitrogen-containing aliphatic heterocyclic group represents a group obtained by removing one hydrogen atom from a carbon atom of a heterocyclic ring of a compound having a nitrogen-containing aliphatic heterocyclic ring. Represents an aliphatic heterocycle having a nitrogen atom as a heteroatom. The nitrogen-containing aromatic heterocyclic group represents a group obtained by removing one hydrogen atom from a carbon atom of a heterocyclic ring of a compound having a nitrogen-containing aromatic heterocyclic ring, and the nitrogen-containing aromatic heterocyclic ring constitutes a ring. An aromatic heterocyclic ring having a nitrogen atom as a hetero atom is represented.

The nitrogen-containing aliphatic heterocyclic group represented by A ¹⁰¹ includes a group having only a nitrogen atom as a hetero atom constituting a ring, a group having a nitrogen atom and an oxygen atom as a hetero atom constituting a ring, and a hetero atom constituting a ring. Examples thereof include a group having a nitrogen atom and a sulfur atom.

The nitrogen-containing aliphatic heterocyclic group having only a nitrogen atom as a hetero atom constituting the ring includes a group having an aziridine ring, a group having an azetidine ring, a group having a pyrrolidine ring, a group having a piperidine ring, a hexamethyleneimine ring , A group having an imidazolidine ring, a group having a piperazine ring, a group having a pyrazolidine ring, and the like.

Examples of the group having an aziridine ring include an N-alkyl-2-aziridinyl group.
Examples of the group having an azetidine ring include an N-alkyl-2-azetidinyl group and an N-alkyl-3-azetidinyl group.
Examples of the group having a pyrrolidine ring include an N-alkyl-2-pyrrolidinyl group and an N-alkyl-3-pyrrolidinyl group.
Examples of the group having a piperidine ring include an N-alkyl-2-piperidinyl group, an N-alkyl-3-piperidinyl group, and an N-alkyl-4-piperidinyl group.
Examples of the group having a hexamethyleneimine ring include an N-alkyl-2-hexamethyleneimino group, an N-alkyl-3-hexamethyleneimino group, and an N-alkyl-4-hexamethyleneimino group.
Examples of the group having an imidazolidine ring include a 1,3-dialkyl-2-imidazolidyl group and a 1,3-dialkyl-4-imidazolidyl group.
Examples of the group having a piperazine ring include a 1,4-dialkyl-2-piperazinyl group.
Examples of the group having a pyrazolidine ring include a 1,2-dialkyl-3-pyrazolidyl group and a 1,2-dialkyl-4-pyrazolidyl group.

Examples of the nitrogen-containing aliphatic heterocyclic group having a nitrogen atom and an oxygen atom as a hetero atom constituting the ring include a group having a morpholine ring and a group having an isoxazolidine ring.

Examples of the group having a morpholine ring include an N-alkyl-2-morpholino group and an N-alkyl-3-morpholino group.
Examples of the group having an isoxazolidine ring include an N-alkyl-3-isoxazolidinyl group, an N-alkyl-4-isoxazolidinyl group, and an N-alkyl-5-isoxazolidinyl group. Can do.

Examples of the nitrogen-containing aliphatic heterocyclic group having a nitrogen atom and a sulfur atom as hetero atoms constituting the ring include a group having a thiomorpholine ring and a group having an isothiazolidine ring.

Examples of the group having a thiomorpholine ring include an N-alkyl-2-thiomorpholino group and an N-alkyl-3-thiomorpholino group.
Examples of the group having an isothiazolidine ring include an N-alkyl-3-isothiazolidinyl group, an N-alkyl-4-isothiazolidinyl group, and an N-alkyl-5-isothiazolidinyl group.

The nitrogen-containing aliphatic heterocyclic group represented by A ¹⁰¹ is preferably a group having only a nitrogen atom as a hetero atom constituting the ring. The number of carbon atoms in the nitrogen-containing aliphatic heterocyclic group is preferably 4-10.

^Examples of the nitrogen-containing aromatic heterocyclic group represented by A ¹⁰¹ include a group having only a nitrogen atom as a hetero atom constituting a ring, a group having a nitrogen atom and an oxygen atom as a hetero atom constituting a ring, and a hetero atom constituting a ring. Examples thereof include a group having a nitrogen atom and a sulfur atom.

The nitrogen-containing aromatic heterocyclic group having only a nitrogen atom as a hetero atom constituting the ring includes a group having a pyrrole ring, a group having an imidazole ring, a group having a pyrazole ring, a group having a pyridine ring, and a pyridazine ring. A group having a pyrimidine ring, a group having a pyrazine ring, a group having a quinoline ring, a group having an isoquinoline ring, a group having a cinnoline ring, a group having a quinazoline ring, a group having a phthalazine ring, and the like.

Examples of the group having a pyrrole ring include a 2-pyrrolyl group, a 3-pyrrolyl group, a 2- (N-methylpyrrolyl) group, and a 3- (N-methylpyrrolyl) group.
Examples of the group having an imidazole ring include 2-imidazolyl group, 4-imidazolyl group, 5-imidazolyl group, 2- (N-methylimidazolyl) group, 4- (N-methylimidazolyl) group, and 5- (N-methylimidazolyl). ) Group.
Examples of the group having a pyrazole ring include 3-pyrazolyl group, 4-pyrazolyl group, 5-pyrazolyl group, 3- (N-methylpyrazolyl) group, 4- (N-methylpyrazolyl) group, and 5- (N-methylpyrazolyl). ) Group.
Examples of the group having a pyridine ring include a 2-pyridyl group, a 3-pyridyl group, and a 4-pyridyl group.
Examples of the group having a pyridazine ring include a 3-pyridazyl group and a 4-pyridazyl group.
Examples of the group having a pyrimidine ring include a 2-pyrimidyl group, a 4-pyrimidyl group, and a 5-pyrimidyl group.
Examples of the group having a pyrazine ring include a 2-pyrazyl group.
Examples of the group having a quinoline ring include a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 5-quinolyl group, a 6-quinolyl group, a 7-quinolyl group, and an 8-quinolyl group.
Examples of the group having an isoquinoline ring include a 1-isoquinolyl group, a 3-isoquinolyl group, a 4-isoquinolyl group, a 5-isoquinolyl group, a 6-isoquinolyl group, a 7-isoquinolyl group, and an 8-isoquinolyl group.
Examples of the group having a cinnoline ring include a 3-cinnolinyl group, a 4-cinnolinyl group, a 5-cinnolinyl group, a 6-cinnolinyl group, a 7-cinnolinyl group, and an 8-cinnolinyl group.
Examples of the group having a quinazoline ring include a 2-quinazolinyl group, a 4-quinazolinyl group, a 5-quinazolinyl group, a 6-quinazolinyl group, a 7-quinazolinyl group, and an 8-quinazolinyl group.
Examples of the group having a phthalazine ring include a 1-phthalazinyl group, a 5-phthalazinyl group, and a 6-phthalazinyl group.
The nitrogen-containing aromatic heterocyclic group having only a nitrogen atom as a hetero atom constituting the ring is preferably a group having an imidazole ring, a group having a pyridine ring, or a group having a quinoline ring.

Examples of the nitrogen-containing aromatic heterocyclic group having a nitrogen atom and an oxygen atom as hetero atoms constituting the ring include a group having an oxazole ring and a group having an isoxazole ring.

Examples of the group having an oxazole ring include a 2-oxazolyl group, a 4-oxazolyl group, and a 5-oxazolyl group.
Examples of the group having an isoxazole ring include a 3-isoxazolyl group, a 4-isoxazolyl group, and a 5-isoxazolyl group.
The nitrogen-containing aromatic heterocyclic group having a nitrogen atom and an oxygen atom as hetero atoms constituting the ring is preferably a group having an oxazole ring.

Examples of the nitrogen-containing aromatic heterocyclic group having a nitrogen atom and a sulfur atom as the hetero atoms constituting the ring include a group having a thiazole ring, a group having an isothiazole ring, and the like.

Examples of the group having a thiazole ring include a 2-thiazolyl group, a 4-thiazolyl group, and a 5-thiazolyl group.
Examples of the group having an isothiazole ring include a 3-isothiazolyl group, a 4-isothiazolyl group, and a 5-isothiazolyl group.
The nitrogen-containing aromatic heterocyclic group having a nitrogen atom and a sulfur atom as a hetero atom constituting the ring is preferably a group having a thiazole ring.

The nitrogen-containing heterocyclic group represented by A ¹⁰¹ is preferably a nitrogen-containing aromatic heterocyclic group, more preferably a nitrogen-containing aromatic heterocyclic group having only a nitrogen atom as a hetero atom constituting the ring, More preferred are a group having an imidazole ring, a group having a pyridine ring, and a group having a quinoline ring, and particularly preferred is a group having a pyridine ring.

Examples of the compound represented by formula (12) include the following compounds as compounds in which R ¹²¹ is a hydrogen atom, n ¹ is 0, and A ¹⁰¹ is a substituted amino group.

1-vinylpyrrolidine,
1-vinyl piperidine,
1-vinylhexamethyleneimine,
1-vinyl piperazine,
1-vinyl pyrrole,
1-vinylimidazole,
1-vinylpyrazole,
Vinyl quinoline.

As the compound represented by the formula (12), R ¹²¹ is a hydrogen atom, n ¹ is 1, R ¹²² is a group represented by the formula (12-Y), and A ¹⁰¹ is a substituted amino group. The following compounds can be mentioned as the compounds.

Compound in which r ^{1 in} formula (12-Y) is 0:
4-N, N-dimethylaminostyrene,
3-N, N-dimethylaminostyrene,
4-N, N-diethylaminostyrene,
3-N, N-diethylaminostyrene,
4-N, N-di-n-propylaminostyrene,
3-N, N-di-n-propylaminostyrene,
4-N, N-di-n-butylaminostyrene,
3-N, N-di-n-butylaminostyrene,
4-N, N-diallylaminostyrene,
3-N, N-diallylaminostyrene,
4-N, N-bis (trimethylsilyl) aminostyrene,
3-N, N-bis (trimethylsilyl) aminostyrene,
4-N, N-bis (tert-butyldimethylsilyl) aminostyrene,
3-N, N-bis (tert-butyldimethylsilyl) aminostyrene,
4- (1-aziridinyl) styrene,
3- (1-aziridinyl) styrene,
4- (1-pyrrolidinyl) styrene,
3- (1-pyrrolidinyl) styrene,
4- (1-piperidinyl) styrene,
3- (1-piperidinyl) styrene,
4- (1-hexamethyleneimino) styrene,
3- (1-Hexamethyleneimino) styrene.

Compound in which r ^{1 in} formula (12-Y) is 1:
4-N, N-dimethylaminomethylstyrene,
3-N, N-dimethylaminomethylstyrene,
4-N, N-diethylaminomethylstyrene,
3-N, N-diethylaminomethylstyrene,
4-N, N-di-n-propylaminomethylstyrene,
3-N, N-di-n-propylaminomethylstyrene,
4-N, N-di-n-butylaminomethylstyrene,
3-N, N-di-n-butylaminomethylstyrene,
4-N, N-diallylaminomethylstyrene,
3-N, N-diallylaminomethylstyrene,
4-N, N-bis (trimethylsilyl) aminomethylstyrene,
3-N, N-bis (trimethylsilyl) aminomethylstyrene,
4-N, N-bis (tert-butyldimethylsilyl) aminomethylstyrene,
3-N, N-bis (tert-butyldimethylsilyl) aminomethylstyrene,
4- (1-aziridinyl) methylstyrene,
3- (1-aziridinyl) methylstyrene,
4- (1-pyrrolidinyl) methylstyrene,
3- (1-pyrrolidinyl) methylstyrene,
4- (1-piperidinyl) methylstyrene,
3- (1-piperidinyl) methylstyrene,
4- (1-hexamethyleneimino) methylstyrene,
3- (1-Hexamethyleneimino) methylstyrene.

Compound in which r ^{1 in} formula (12-Y) is 2:
4-N, N-dimethylaminoethylstyrene,
3-N, N-dimethylaminoethylstyrene,
4-N, N-diethylaminoethylstyrene,
3-N, N-diethylaminoethylstyrene,
4-N, N-di-n-propylaminoethylstyrene,
3-N, N-di-n-propylaminoethylstyrene,
4-N, N-di-n-butylaminoethylstyrene,
3-N, N-di-n-butylaminoethylstyrene,
4-N, N-diallylaminoethylstyrene,
3-N, N-diallylaminoethylstyrene,
4-N, N-bis (trimethylsilyl) aminoethylstyrene,
3-N, N-bis (trimethylsilyl) aminoethylstyrene,
4-N, N-bis (tert-butyldimethylsilyl) aminoethylstyrene,
3-N, N-bis (tert-butyldimethylsilyl) aminoethylstyrene,
4- (1-aziridinyl) ethylstyrene,
3- (1-aziridinyl) ethylstyrene,
4- (1-pyrrolidinyl) ethylstyrene,
3- (1-pyrrolidinyl) ethylstyrene,
4- (1-piperidinyl) ethylstyrene,
3- (1-piperidinyl) ethylstyrene,
4- (1-hexamethyleneimino) ethylstyrene,
3- (1-Hexamethyleneimino) ethylstyrene.

Examples of the compound represented by formula (12) include the following compounds as compounds in which R ¹²¹ is a methyl group, n ¹ is 0, and A ¹⁰¹ is a substituted amino group.

1-isopropenylpyrrolidine,
1-isopropenyl piperidine,
1-isopropenyl hexamethyleneimine,
1-isopropenyl piperazine,
1-isopropenyl pyrrole,
1-isopropenylimidazole,
1-isopropenylpyrazole,
Isopropenyl quinoline.

As the compound represented by the formula (12), R ¹²¹ is a methyl group, n ¹ is 1, R ¹²² is a group represented by the formula (12-Y), and A ¹⁰¹ is a substituted amino group. The following compounds can be mentioned as the compounds.

Compound in which r ^{1 in} formula (12-Y) is 0:
4-N, N-dimethylaminoisopropenylbenzene,
3-N, N-dimethylaminoisopropenylbenzene,
4-N, N-diethylaminoisopropenylbenzene,
3-N, N-diethylaminoisopropenylbenzene,
4-N, N-di-n-propylaminoisopropenylbenzene,
3-N, N-di-n-propylaminoisopropenylbenzene,
4-N, N-di-n-butylaminoisopropenylbenzene,
3-N, N-di-n-butylaminoisopropenylbenzene,
4-N, N-diallylaminoisopropenylbenzene,
3-N, N-diallylaminoisopropenylbenzene,
4-N, N-bis (trimethylsilyl) aminoisopropenylbenzene,
3-N, N-bis (trimethylsilyl) aminoisopropenylbenzene,
4-N, N-bis (tert-butyldimethylsilyl) aminoisopropenylbenzene, 3-N, N-bis (tert-butyldimethylsilyl) aminoisopropenylbenzene, 4- (1-aziridinyl) isopropenylbenzene,
3- (1-aziridinyl) isopropenylbenzene,
4- (1-pyrrolidinyl) isopropenylbenzene,
3- (1-pyrrolidinyl) isopropenylbenzene,
4- (1-piperidinyl) isopropenylbenzene,
3- (1-piperidinyl) isopropenylbenzene,
4- (1-hexamethyleneimino) isopropenylbenzene,
3- (1-Hexamethyleneimino) isopropenylbenzene.

Compound in which r ^{1 in} formula (12-Y) is 1:
4-N, N-dimethylaminomethylisopropenylbenzene,
3-N, N-dimethylaminomethylisopropenylbenzene,
4-N, N-diethylaminomethylisopropenylbenzene,
3-N, N-diethylaminomethylisopropenylbenzene,
4-N, N-di-n-propylaminomethylisopropenylbenzene,
3-N, N-di-n-propylaminomethylisopropenylbenzene,
4-N, N-di-n-butylaminomethylisopropenylbenzene,
3-N, N-di-n-butylaminomethylisopropenylbenzene,
4-N, N-diallylaminomethylisopropenylbenzene,
3-N, N-diallylaminomethylisopropenylbenzene,
4-N, N-bis (trimethylsilyl) aminomethylisopropenylbenzene,
3-N, N-bis (trimethylsilyl) aminomethylisopropenylbenzene,
4-N, N-bis (tert-butyldimethylsilyl) aminomethylisopropenylbenzene,
3-N, N-bis (tert-butyldimethylsilyl) aminomethylisopropenylbenzene,
4- (1-aziridinyl) methylisopropenylbenzene,
3- (1-aziridinyl) methyl isopropenylbenzene,
4- (1-pyrrolidinyl) methylisopropenylbenzene,
3- (1-pyrrolidinyl) methylisopropenylbenzene,
4- (1-piperidinyl) methyl isopropenylbenzene,
3- (1-piperidinyl) methylisopropenylbenzene,
4- (1-hexamethyleneimino) methylisopropenylbenzene,
3- (1-Hexamethyleneimino) methylisopropenylbenzene.

Compound in which r ^{1 in} formula (12-Y) is 2:
4-N, N-dimethylaminoethylisopropenylbenzene,
3-N, N-dimethylaminoethylisopropenylbenzene,
4-N, N-diethylaminoethylisopropenylbenzene,
3-N, N-diethylaminoethylisopropenylbenzene,
4-N, N-di-n-propylaminoethylisopropenylbenzene,
3-N, N-di-n-propylaminoethylisopropenylbenzene,
4-N, N-di-n-butylaminoethylisopropenylbenzene,
3-N, N-di-n-butylaminoethyl isopropenylbenzene,
4-N, N-diallylaminoethyl isopropenylbenzene,
3-N, N-diallylaminoethylisopropenylbenzene,
4-N, N-bis (trimethylsilyl) aminoethylisopropenylbenzene,
3-N, N-bis (trimethylsilyl) aminoethylisopropenylbenzene,
4-N, N-bis (tert-butyldimethylsilyl) aminoethylisopropenylbenzene,
3-N, N-bis (tert-butyldimethylsilyl) aminoethylisopropenylbenzene,
4- (1-aziridinyl) ethyl isopropenylbenzene,
3- (1-aziridinyl) ethyl isopropenylbenzene,
4- (1-pyrrolidinyl) ethyl isopropenylbenzene,
3- (1-pyrrolidinyl) ethyl isopropenylbenzene,
4- (1-piperidinyl) ethyl isopropenylbenzene,
3- (1-piperidinyl) ethyl isopropenylbenzene,
4- (1-hexamethyleneimino) ethyl isopropenylbenzene,
3- (1-Hexamethyleneimino) ethyl isopropenylbenzene.

Examples of the compound represented by formula (12) include the following compounds as compounds in which R ¹²¹ is a vinyl group, n ¹ is 0, and A ¹⁰¹ is a substituted amino group.

2-N, N-dimethylamino-1,3-butadiene,
2-N, N-diethylamino-1,3-butadiene,
2-N, N-di-n-propylamino-1,3-butadiene,
2-N, N-di-n-butylamino-1,3-butadiene,
2-N, N-diallylamino-1,3-butadiene,
2-N, N-bis (trimethylsilyl) amino-1,3-butadiene,
2-N, N-bis (tert-butyldimethylsilyl) amino-1,3-butadiene,
2- (1-aziridinyl) -1,3-butadiene,
2- (1-pyrrolidinyl) -1,3-butadiene,
2- (1-piperidinyl) -1,3-butadiene,
2- (1-hexamethyleneimino) -1,3-butadiene,
2- (1-pyrrolyl) -1,3-butadiene,
2- (1-imidazolyl) -1,3-butadiene,
2- (1-Pyrazolyl) -1,3-butadiene.

As a compound represented by the formula (12), R ¹²¹ is a vinyl group, n ¹ is 1, R ¹²² is an alkylene group, and A ¹⁰¹ is a substituted amino group. I can give you.

Compound in which R ¹²² is a methylene group:
2-N, N-dimethylaminomethyl-1,3-butadiene,
2-N, N-diethylaminomethyl-1,3-butadiene,
2-N, N-di-n-propylaminomethyl-1,3-butadiene,
2-N, N-di-n-butylaminomethyl-1,3-butadiene,
2-N, N-diallylaminomethyl-1,3-butadiene,
2-N, N-bis (trimethylsilyl) aminomethyl-1,3-butadiene,
2-N, N-bis (tert-butyldimethylsilyl) aminomethyl-1,3-butadiene,
2- (1-aziridinyl) methyl-1,3-butadiene,
2- (1-pyrrolidinyl) methyl-1,3-butadiene,
2- (1-piperidinyl) methyl-1,3-butadiene,
2- (1-hexamethyleneimino) methyl-1,3-butadiene,
1- (2-methylene-3-butenyl) pyrrole,
1- (2-methylene-3-butenyl) imidazole,
1- (2-Methylene-3-butenyl) pyrazole.

Compounds in which R ¹²² is an ethylene group:
5-N, N-dimethylamino-3-methylene-1-pentene,
5-N, N-diethylamino-3-methylene-1-pentene,
5-N, N-di-n-propylamino-3-methylene-1-pentene,
5-N, N-di-n-butylamino-3-methylene-1-pentene,
5-N, N-diallylamino-3-methylene-1-pentene,
5-N, N-bis (trimethylsilyl) amino-3-methylene-1-pentene,
5-N, N-bis (tert-butyldimethylsilyl) amino-3-methylene-1-pentene,
5- (1-aziridinyl) -3-methylene-1-pentene,
5- (1-pyrrolidinyl) -3-methylene-1-pentene,
5- (1-piperidinyl) -3-methylene-1-pentene,
5- (1-hexamethyleneimino) -3-methylene-1-pentene,
1- (3-methylene-4-pentenyl) pyrrole,
1- (3-methylene-4-pentenyl) imidazole,
1- (3-methylene-4-pentenyl) pyrazole.

As the compound represented by the formula (12), R ¹²¹ is a hydrogen atom, n ¹ is 1, R ¹²² is a group represented by the formula (12-Y), and A ¹⁰¹ is a nitrogen-containing fat. Examples of the compound which is a group heterocyclic group include the following compounds.

Compound in which r ^{1 in} formula (12-Y) is 0:
4-N-methyl-2-aziridinylstyrene,
4-N-methyl-2-pyrrolidinylstyrene,
4-N-methyl-3-pyrrolidinylstyrene,
4-N-methyl-2-hexamethyleneiminostyrene,
4-N-methyl-3-hexamethyleneiminostyrene,
4-N-methyl-4-hexamethyleneiminostyrene.

Compound in which r ^{1 in} formula (12-Y) is 1:
4-N-methyl-2-aziridinylmethylstyrene,
4-N-methyl-2-pyrrolidinylmethylstyrene,
4-N-methyl-3-pyrrolidinylmethylstyrene,
4-N-methyl-2-hexamethyleneiminomethylstyrene,
4-N-methyl-3-hexamethyleneiminomethylstyrene,
4-N-methyl-4-hexamethyleneiminomethylstyrene.

Compound in which r ^{1 in} formula (12-Y) is 2:
4-N-methyl-2-aziridinylethylstyrene,
4-N-methyl-2-pyrrolidinylethylstyrene,
4-N-methyl-3-pyrrolidinylethylstyrene,
4-N-methyl-2-hexamethyleneiminoethylstyrene,
4-N-methyl-3-hexamethyleneiminoethylstyrene,
4-N-methyl-4-hexamethyleneiminoethylstyrene.

As the compound represented by the formula (12), R ¹²¹ is a methyl group, n ¹ is 1, R ¹²² is a group represented by the formula (12-Y), and A ¹⁰¹ is a nitrogen-containing fat. Examples of the compound which is a group heterocyclic group include the following compounds.

Compound in which r ^{1 in} formula (12-Y) is 0:
4-N-methyl-2-aziridinylisopropenylbenzene,
4-N-methyl-2-pyrrolidinylisopropenylbenzene,
4-N-methyl-3-pyrrolidinylisopropenylbenzene,
4-N-methyl-2-hexamethyleneiminoisopropenylbenzene,
4-N-methyl-3-hexamethyleneiminoisopropenylbenzene,
4-N-methyl-4-hexamethyleneiminoisopropenylbenzene.

Compound in which r ^{1 in} formula (12-Y) is 1:
4-N-methyl-2-aziridinylmethyl isopropenylbenzene,
4-N-methyl-2-pyrrolidinylmethylisopropenylbenzene,
4-N-methyl-3-pyrrolidinylmethylisopropenylbenzene,
4-N-methyl-2-hexamethyleneiminomethylisopropenylbenzene,
4-N-methyl-3-hexamethyleneiminomethylisopropenylbenzene,
4-N-methyl-4-hexamethyleneiminomethylisopropenylbenzene.

Compound in which r ^{1 in} formula (12-Y) is 2:
4-N-methyl-2-aziridinylethyl isopropenylbenzene,
4-N-methyl-2-pyrrolidinylethyl isopropenylbenzene,
4-N-methyl-3-pyrrolidinylethyl isopropenylbenzene,
4-N-methyl-2-hexamethyleneiminoethylisopropenylbenzene,
4-N-methyl-3-hexamethyleneiminoethyl isopropenylbenzene,
4-N-methyl-4-hexamethyleneiminoethylisopropenylbenzene.

Examples of the compound represented by the formula (12) include the following compounds as compounds in which R ¹²¹ is a vinyl group, n ¹ is 0, and A ¹⁰¹ is a nitrogen-containing aliphatic heterocyclic group. .

N-methyl-2- (1-methylene-2-propenyl) aziridine,
N-methyl-2- (1-methylene-2-propenyl) pyrrolidine,
N-methyl-3- (1-methylene-2-propenyl) pyrrolidine,
N-methyl-2- (1-methylene-2-propenyl) hexamethyleneimine,
N-methyl-3- (1-methylene-2-propenyl) hexamethyleneimine,
N-methyl-4- (1-methylene-2-propenyl) hexamethyleneimine.

As a compound represented by the formula (12), R ¹²¹ is a vinyl group, n ¹ is 1, R ¹²² is an alkylene group, and A ¹⁰¹ is a nitrogen-containing aliphatic heterocyclic group. The following compounds can be mentioned.

Compound in which R ¹²² is a methylene group:
N-methyl-2- (2-methylene-3-butenyl) aziridine,
N-methyl-2- (2-methylene-3-butenyl) pyrrolidine,
N-methyl-3- (2-methylene-3-butenyl) pyrrolidine,
N-methyl-2- (2-methylene-3-butenyl) hexamethyleneimine,
N-methyl-3- (2-methylene-3-butenyl) hexamethyleneimine,
N-methyl-4- (2-methylene-3-butenyl) hexamethyleneimine.

Compounds in which R ¹²² is an ethylene group:
N-methyl-2- (3-methylene-4-pentenyl) aziridine,
N-methyl-2- (3-methylene-4-pentenyl) pyrrolidine,
N-methyl-3- (3-methylene-4-pentenyl) pyrrolidine,
N-methyl-2- (3-methylene-4-pentenyl) hexamethyleneimine,
N-methyl-3- (3-methylene-4-pentenyl) hexamethyleneimine,
N-methyl-4- (3-methylene-4-pentenyl) hexamethyleneimine.

Examples of the compound represented by formula (12) include the following compounds as compounds in which R ¹²¹ is a hydrogen atom, n ¹ is 0, and A ¹⁰¹ is a nitrogen-containing aromatic heterocyclic group. .

N-methyl-2-vinylimidazole,
N-methyl-4-vinylimidazole,
N-methyl-5-vinylimidazole,
2-vinylpyridine,
3-vinylpyridine,
4-vinylpyridine,
2-vinylquinoline,
3-vinyl quinoline,
4-Vinylquinoline.

Examples of the compound represented by formula (12) include the following compounds as compounds in which R ¹²¹ is a methyl group, n ¹ is 0, and A ¹⁰¹ is a nitrogen-containing aromatic heterocyclic group. .

N-methyl-2-isopropenylimidazole,
N-methyl-4-isopropenylimidazole,
N-methyl-5-isopropenylimidazole,
2-isopropenyl pyridine,
3-isopropenyl pyridine,
4-isopropenyl pyridine,
2-isopropenyl quinoline,
3-isopropenyl quinoline,
4-Isopropenylquinoline.

Examples of the compound represented by formula (12) include the following compounds as compounds in which R ¹²¹ is a vinyl group, n ¹ is 0, and A ¹⁰¹ is a nitrogen-containing aromatic heterocyclic group. .

N-methyl-2- (1-methylene-2-propenyl) imidazole,
N-methyl-4- (1-methylene-2-propenyl) imidazole,
N-methyl-5- (1-methylene-2-propenyl) imidazole,
2- (1-methylene-2-propenyl) pyridine,
3- (1-methylene-2-propenyl) pyridine,
4- (1-methylene-2-propenyl) pyridine,
2- (1-methylene-2-propenyl) quinoline,
3- (1-methylene-2-propenyl) quinoline,
4- (1-methylene-2-propenyl) quinoline.

As the compound represented by the formula (12), R ¹²¹ is a vinyl group, n ¹ is 1, R ¹²² is an alkylene group, and A ¹⁰¹ is a nitrogen-containing aromatic heterocyclic group. The following compounds can be mentioned.

Compound in which R ¹²² is a methylene group:
N-methyl-2- (2-methylene-3-butenyl) imidazole,
N-methyl-4- (2-methylene-3-butenyl) imidazole,
N-methyl-5- (2-methylene-3-butenyl) imidazole,
2- (2-methylene-3-butenyl) pyridine,
3- (2-methylene-3-butenyl) pyridine,
4- (2-methylene-3-butenyl) pyridine,
2- (2-methylene-3-butenyl) quinoline,
3- (2-methylene-3-butenyl) quinoline,
4- (2-Methylene-3-butenyl) quinoline.

Compounds in which R ¹²² is an ethylene group:
N-methyl-2- (3-methylene-4-pentenyl) imidazole,
N-methyl-4- (3-methylene-4-pentenyl) imidazole,
N-methyl-5- (3-methylene-4-pentenyl) imidazole,
2- (3-methylene-4-pentenyl) pyridine,
3- (3-methylene-4-pentenyl) pyridine,
4- (3-methylene-4-pentenyl) pyridine,
2- (3-methylene-4-pentenyl) quinoline,
3- (3-methylene-4-pentenyl) quinoline,
4- (3-Methylene-4-pentenyl) quinoline.

As the compound represented by the formula (12), preferably, R ¹²¹ is a hydrogen atom, n is 1, R ¹²² is a group represented by the formula (12-Y), and A is a substituted amino group. It is a compound that is a group. More preferably, R ¹²¹ is a hydrogen atom, n ¹ is 1, R ¹²² is a group represented by the formula (12-Y), and A ¹⁰¹ is a group represented by the formula (12-X). It is a compound which is. More preferably, the compound ^{R 123} and ^{R 124} is a straight-chain alkyl group having a carbon number of 1-2 of the formula (12-X), compound ^{R 123} and ^{R 124} is a trimethylsilyl group of the formula (12-X) And R ¹²³ and R ¹²⁴ in formula (12-X) are bonded to each other, and the group is a polymethylene group having 4 to 6 carbon atoms.

The compound represented by the formula (12) is particularly preferably
4-N, N-bis (trimethylsilyl) aminostyrene,
3-N, N-bis (trimethylsilyl) aminostyrene,
4-N, N-dimethylaminomethylstyrene,
3-N, N-dimethylaminomethylstyrene,
4- (1-pyrrolidinyl) ethylstyrene,
3- (1-pyrrolidinyl) ethylstyrene.

The content of the monomer unit based on the compound represented by the formula (11) is preferably 0.01% by mass or more per 100% by mass of the conjugated diene polymer in order to improve fuel efficiency. Preferably it is 0.02 mass% or more, More preferably, it is 0.05 mass% or more. In order to improve economy and wear resistance, the content is preferably 20% by mass or less, more preferably 2% by mass or less, still more preferably 1% by mass or less, and particularly preferably 0.5% by mass or less.

In the monomer unit based on the compound represented by the formula (11), the groups represented by X ¹⁰¹ , X ¹⁰² and X ¹⁰³ may be a hydroxyl group by hydrolysis or the like.

The content of the monomer unit based on the compound represented by the formula (12) is preferably 0.01% by mass or more per 100% by mass of the conjugated diene polymer in order to improve fuel efficiency and wear resistance. More preferably, it is 0.02 mass% or more, More preferably, it is 0.05 mass% or more. In order to improve economy and wear resistance, the content is preferably 20% by mass or less, more preferably 2% by mass or less, still more preferably 1% by mass or less, and particularly preferably 0.5% by mass or less.

The conjugated diene polymer (A) according to the first aspect of the present invention may have a structural unit (vinyl aromatic hydrocarbon unit) based on a vinyl aromatic hydrocarbon in order to improve wear resistance. Examples of the vinyl aromatic hydrocarbon include styrene, α-methylstyrene, vinyl toluene, vinyl naphthalene, divinyl benzene, trivinyl benzene, and divinyl naphthalene. Styrene is preferable.

The content of the vinyl aromatic hydrocarbon unit is 0% by mass or more (the content of the conjugated diene unit is 100% by mass or less), where the total amount of the conjugated diene unit and the vinyl aromatic hydrocarbon unit is 100% by mass. The content is preferably 10% by mass or more (the content of the conjugated diene unit is 90% by mass or less), and more preferably 15% by mass or more (the content of the conjugated diene unit is 85% by mass or less). In order to improve fuel economy, the content of vinyl aromatic hydrocarbon units is preferably 50% by mass or less (the content of conjugated diene units is 50% by mass or more), more preferably 45% by mass or less. (The content of the conjugated diene unit is 55% by mass or more).

The Mooney viscosity (ML _{1 + 4} ) of the conjugated diene polymer (A) is preferably 10 or more, more preferably 20 or more, in order to increase the wear resistance. Moreover, in order to improve workability, Preferably it is 200 or less, More preferably, it is 150 or less. The Mooney viscosity (ML _{1 + 4} ) is measured at 100 ° C. according to JIS K 6300 (1994).

The vinyl bond content of the conjugated diene polymer (A) is preferably 80 mol% or less, more preferably 70 mol% or less, in order to improve fuel efficiency, with the content of the conjugated diene unit being 100 mol%. It is. Moreover, in order to improve wet grip property, Preferably it is 10 mol% or more, More preferably, it is 15 mol% or more, More preferably, it is 20 mol% or more, Most preferably, it is 40 mol% or more. The vinyl bond amount is determined from the absorption intensity in the vicinity of 910 cm ^−1, which is the absorption peak of the vinyl group, by infrared spectroscopy.

The molecular weight distribution of the conjugated diene polymer (A) is preferably 1 to 5 and more preferably 1 to 2 in order to improve fuel efficiency. The molecular weight distribution is obtained by measuring the number average molecular weight (Mn) and the weight average molecular weight (Mw) by gel permeation chromatography (GPC) method and dividing Mw by Mn.

As a preferred method for producing the conjugated diene polymer (A), a conjugated diene, a monomer represented by the above formula (11), and the above formula (12) are represented by an alkali metal catalyst in a hydrocarbon solvent. A method of polymerizing a monomer component containing the monomer to be produced can be mentioned.

Examples of the alkali metal catalyst include alkali metals, organic alkali metal compounds, complexes of alkali metals and polar compounds, oligomers having alkali metals, and the like. Examples of the alkali metal include lithium, sodium, potassium, rubidium, cesium and the like. Examples of the organic alkali metal compound include ethyl lithium, n-propyl lithium, iso-propyl lithium, n-butyl lithium, sec-butyl lithium, t-octyl lithium, n-decyl lithium, phenyl lithium, 2-naphthyl lithium, 2 -Butylphenyllithium, 4-phenylbutyllithium, cyclohexyllithium, 4-cyclopentyllithium, dimethylaminopropyllithium, diethylaminopropyllithium, t-butyldimethylsiloxypropyllithium, N-morpholinopropyllithium, lithium hexamethyleneimide, lithium pyrrole Zido, lithium piperidide, lithium heptamethylene imide, lithium dodecamethylene imide, 1,4-dilithio-2-butene, sodium naphthalenide, sodium Bifenirido, such as potassium napthalenide can be mentioned. Examples of the complex of the alkali metal and the polar compound include potassium-tetrahydrofuran complex and potassium-diethoxyethane complex, and the oligomer having the alkali metal includes sodium salt of α-methylstyrene tetramer. I can give you. An organic lithium compound or an organic sodium compound is preferable, and an organic lithium compound having 2 to 20 carbon atoms or an organic sodium compound having 2 to 20 carbon atoms is more preferable.

The hydrocarbon solvent is a solvent that does not deactivate the organic alkali metal compound catalyst, and examples thereof include aliphatic hydrocarbons, aromatic hydrocarbons, and alicyclic hydrocarbons.
Examples of the aliphatic hydrocarbon include propane, n-butane, iso-butane, n-pentane, iso-pentane, n-hexane, propene, 1-butene, iso-butene, trans-2-butene, cis-2- Examples include butene, 1-pentene, 2-pentene, 1-hexene, 2-hexene and the like. Examples of the aromatic hydrocarbon include benzene, toluene, xylene, and ethylbenzene. Examples of the alicyclic hydrocarbon include cyclopentane and cyclohexane. One or more of these may be used, and the hydrocarbon solvent may be a mixture of various components such as industrial hexane. Preferably, it is a hydrocarbon having 2 to 12 carbon atoms.

A monomer component containing a conjugated diene, a compound represented by the above formula (11) and a compound represented by the above formula (12) is polymerized with an alkali metal catalyst in a hydrocarbon solvent, and a monomer based on the conjugated diene is obtained. A polymer having a monomer unit, a monomer unit based on the compound represented by the formula (11) and a monomer unit based on the compound represented by the formula (12) is produced. Examples of the conjugated diene include 1,3-butadiene, isoprene, 1,3-pentadiene, 2,3-dimethyl-1,3-butadiene, and 1,3-hexadiene. One or more of these are used. 1,3-butadiene and isoprene are preferred.

The amount of the compound represented by the formula (11) is preferably 0.01% by mass or more in order to improve the fuel efficiency by setting the total amount of the monomer components used in the polymerization to 100% by mass. More preferably, it is 0.02 mass% or more, More preferably, it is 0.05 mass% or more. In order to improve economic efficiency and wear resistance, it is preferably 20% by mass or less, more preferably 2% by mass or less, still more preferably 1% by mass or less, and particularly preferably 0.5% by mass or less. is there.

The amount of the compound represented by the formula (12) is preferably 0.01% by mass, in order to improve the fuel efficiency and wear resistance, with the total amount of monomer components used in the polymerization being 100% by mass. % Or more, more preferably 0.02 mass% or more, still more preferably 0.05 mass% or more. In order to improve economic efficiency and wear resistance, it is preferably 20% by mass or less, more preferably 2% by mass or less, still more preferably 1% by mass or less, and particularly preferably 0.5% by mass or less. is there.

Polymerization may be carried out by combining a conjugated diene, a compound represented by the formula (11) and a compound represented by the formula (12) with a vinyl aromatic hydrocarbon. Examples of the vinyl aromatic hydrocarbon include styrene, α -Methylstyrene, vinyltoluene, vinylnaphthalene, divinylbenzene, trivinylbenzene, divinylnaphthalene and the like can be mentioned. Styrene is preferable.

The amount of vinyl aromatic hydrocarbon used is preferably 10% by mass or more (the amount of conjugated diene used) in order to increase the strength with the total amount of conjugated diene and vinyl aromatic hydrocarbon being 100% by mass. Is 90% by mass or less), more preferably 15% by mass or more (the amount of conjugated diene used is 85% by mass or less). In order to improve fuel efficiency, the amount of vinyl aromatic hydrocarbon used is preferably 50% by mass or less (the amount of conjugated diene used is 50% by mass or more), more preferably 45% by mass or less (conjugated). The amount of diene used is 55% by mass or more).

Further, in the polymerization reaction, the total amount of the conjugated diene, the compound represented by the formula (11), the compound represented by the formula (12) and the vinyl aromatic hydrocarbon is 100%. In order to increase the strength, it is preferably 99.9% by mass or more, more preferably 99.95% by mass or more, and still more preferably 100% by mass.

Polymerization reaction is an agent that adjusts the amount of vinyl bonds of conjugated diene units, an agent that adjusts the distribution of monomer units based on monomers other than conjugated diene units and conjugated dienes in the conjugated diene polymer chain , And collectively referred to as “regulators”). Examples of such agents include ether compounds, tertiary amines, and phosphine compounds. Examples of the ether compound include cyclic ethers such as tetrahydrofuran, tetrahydropyran, and 1,4-dioxane; aliphatic monoethers such as diethyl ether and dibutyl ether; ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, and diethylene glycol diethyl ether. And aliphatic diethers such as diethylene glycol dibutyl ether; aromatic ethers such as diphenyl ether and anisole. Examples of the tertiary amine include triethylamine, tripropylamine, tributylamine, N, N, N ′, N′-tetramethylethylenediamine, N, N-diethylaniline, pyridine, quinoline and the like. Examples of the phosphine compound include trimethylphosphine, triethylphosphine, triphenylphosphine, and the like. One or more of these are used.

The polymerization temperature is usually 25 to 100 ° C, preferably 35 to 90 ° C.
More preferably, it is 50-80 degreeC. The polymerization time is usually 10 minutes to 5 hours.

（式中、Ｖ^２０１は重合性炭素−炭素二重結合を有するヒドロカルビル基を表し、Ｓ^２０１は置換シリル基を表す。）

（式中、Ｖ^２０２は重合性炭素−炭素二重結合を有するヒドロカルビル基を表し、Ａ^２０２は置換アミノ基、又は、含窒素複素環基を表す。） The conjugated diene polymer (B) according to the second present invention includes a monomer unit based on a conjugated diene, a monomer unit based on a compound represented by the following formula (21), and the following formula (22). It is obtained by reacting an alkoxysilane compound with one end of a copolymer having a monomer unit based on the compound represented by the formula:

(In the formula, V ²⁰¹ represents a hydrocarbyl group having a polymerizable carbon-carbon double bond, and S ²⁰¹ represents a substituted silyl group.)

(In the formula, V ²⁰² represents a hydrocarbyl group having a polymerizable carbon-carbon double bond, and A ²⁰² represents a substituted amino group or a nitrogen-containing heterocyclic group.)

As used herein, a hydrocarbyl group represents a hydrocarbon residue. The hydrocarbylene group represents a divalent hydrocarbon residue. A nitrogen-containing heterocyclic group represents a group obtained by removing one hydrogen atom from a carbon atom of a heterocyclic ring of a compound having a nitrogen-containing heterocyclic ring, and the nitrogen-containing heterocyclic ring is an aromatic having a nitrogen atom as a hetero atom constituting the ring. Represents a family heterocycle.

Examples of the conjugated diene include 1,3-butadiene, isoprene, 1,3-pentadiene, 2,3-dimethyl-1,3-butadiene, 1,3-hexadiene and the like, and one or more of these are used. . The conjugated diene is preferably 1,3-butadiene or isoprene.

V ²⁰¹ in the formula (21) represents a hydrocarbyl group having a polymerizable carbon-carbon double bond.

V ²⁰¹ is preferably a group represented by the following formula (21-V).

（式中、ｎ^２は０又は１であり、Ｒ^２１１、Ｒ^２１３及びＲ^２１４は、それぞれ独立に水素原子又はヒドロカルビル基を表し、Ｒ^２１２はヒドロカルビレン基を表す。）

(In the formula, n ² is 0 or 1, R ²¹¹ , R ²¹³ and R ²¹⁴ each independently represent a hydrogen atom or a hydrocarbyl group, and R ²¹² represents a hydrocarbylene group.)

In the formula (21-V), n ² represents 0 or 1.

^Examples of the hydrocarbyl group of R ²¹¹ , R ²¹³ and R ²¹⁴ include an alkyl group, an alkenyl group, and an aryl group. Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, and a tert-butyl group, and a methyl group is preferable. Examples of the alkenyl group include a vinyl group, an allyl group, a 1-propenyl group, and a 1-methylethenyl group, and a vinyl group is preferable. Examples of the aryl group include a phenyl group, a methylphenyl group, and an ethylphenyl group, and a phenyl group is preferable.

R ²¹¹ , R ²¹³ and R ²¹⁴ are preferably a hydrogen atom, a methyl group, a vinyl group, or a phenyl group, and more preferably a hydrogen atom.

^Examples of the hydrocarbylene group for R ²¹² include an alkylene group, an arylene group, and a group in which an arylene group and an alkylene group are bonded.

Examples of the alkylene group include a methylene group, an ethylene group, and a trimethylene group. Preferably, it is a methylene group or an ethylene group. Examples of the arylene group include a phenylene group, a naphthylene group, and a biphenylene group. A phenylene group is preferred.

Examples of the group in which an arylene group and an alkylene group are bonded include a group in which a phenylene group and an alkylene group are bonded, a group in which a naphthylene group and an alkylene group are bonded, and a group in which a biphenylene group and an alkylene group are bonded. .
Moreover, as the group in which the arylene group and the alkylene group are bonded, it is preferable that the carbon atom of the arylene group of the group is bonded to the carbon atom to which R ²¹¹ of the formula (21-V) is bonded.

In a group in which a phenylene group and an alkylene group are bonded (phenylene-alkylene group (for example, a group represented by the following formula (21-R))), the position of a carbon atom on the benzene ring from which a hydrogen atom has been removed; Depending on the position of the carbon atom on the benzene ring to which the alkylene group is bonded, a para-phenylene-alkylene group (for example, a group represented by the following formula (21-Ra)), a meta-phenylene-alkylene group (for example, A group represented by the following formula (21-Rb)), and an ortho-phenylene-alkylene group (for example, a group represented by the following formula (21-Rc)).

（式中、ｄ^２は１〜１０の整数を表し、（ＣＨ_２）_ｄ２はベンゼン環上の置換基である。）

(In the formula, d ² represents an integer of 1 to 10, and (CH ₂ ) _{d 2} is a substituent on the benzene ring.)

（式中、ｅ^２、ｆ^２、ｇ^２は、それぞれ、１〜１０の整数を表す。）

(Wherein e ² , f ² and g ² each represents an integer of 1 to 10)

The group in which an arylene group and an alkylene group are bonded is preferably a group in which a phenylene group and an alkylene group are bonded, and more preferably a group represented by the above formula (21-Ra) or the above formula (21 -Rb), more preferably a para-phenylene-methylene group (a group represented by the formula (21-Ra) where e ² = 1), a meta-phenylene-methylene group (f ^2). = 1 group represented by formula (21-Rb)), para-phenylene-ethylene group (group represented by formula (21-Ra) where e ² = 2), meta-phenylene-ethylene group ( group represented by the formula (21-Rb) where f ² = 2.

Examples of the group represented by the formula (21-V) include the following groups.

As a group in which R ²¹¹ , R ²¹³ and R ²¹⁴ are hydrogen atoms, a vinyl group, a vinylmethyl group, a vinylethyl group, a 4-vinylphenyl group, a 3-vinylphenyl group, a (4-vinylphenyl) methyl group, 2- ( 4-vinylphenyl) ethyl group, (3-vinylphenyl) methyl group, 2- (3-vinylphenyl) ethyl group and the like can be mentioned.

R ²¹¹ is a methyl group, and R ²¹³ and R ²¹⁴ are hydrogen atoms, such as an isopropenyl group, a methallyl group, a 4-isopropenylphenyl group, a 3-isopropenylphenyl group, and (4-isopropenylphenyl) methyl. Group, 2- (4-isopropenylphenyl) ethyl group, (3-isopropenylphenyl) methyl group, 2- (3-isopropenylphenyl) ethyl group and the like.

^Examples of the group in which R ²¹¹ is a vinyl group and R ²¹³ and R ²¹⁴ are hydrogen atoms include a 1-methylene-2-propenyl group and a 2-methylene-3-butenyl group.

^Examples of the group in which R ²¹¹ is a phenyl group and R ²¹³ and R ²¹⁴ are hydrogen atoms include 4- (1-phenylvinyl) phenyl group, 3- (1-phenylvinyl) phenyl group, and 2- (1-phenylvinyl). ) A phenyl group can be mentioned.

^Examples of the group in which R ²¹¹ is a hydrogen atom, R ²¹³ is a methyl group, and R ²¹⁴ is a hydrogen atom include a 1-propenyl group, a crotyl group, a 4- (1-propenyl) phenyl group, and a 4- (1-propenyl group). ) Phenylmethyl group, 2- {4- (1-propenyl) phenyl} ethyl group, 3- (1-propenyl) phenyl group, 3- (1-propenyl) phenylmethyl group, 2- {3- (1-propenyl) ) Phenyl} ethyl group and the like.

（式中、Ｒ^２１１は水素原子又はヒドロカルビル基を表し、ｎ^２は０又は１であり、Ｒ^２１２はヒドロカルビレン基を表す。） The group represented by the formula (21-V) is preferably a group represented by the following formula (21-V1).

(Wherein R ²¹¹ represents a hydrogen atom or a hydrocarbyl group, n ² is 0 or 1, and R ²¹² represents a hydrocarbylene group.)

The group represented by the formula (21-V1) is preferably a group in which ^R211 is a hydrogen atom, such as vinyl group, 4-vinylphenyl group, 3-vinylphenyl group, (4-vinylphenyl) methyl group, 2 -(4-vinylphenyl) ethyl group, (3-vinylphenyl) methyl group, 2- (3-vinylphenyl) ethyl group; ^R211 is a methyl group as 4-isopropenylphenyl group, 3-iso A propenylphenyl group, (4-isopropenylphenyl) methyl group, 2- (4-isopropenylphenyl) ethyl group, (3-isopropenylphenyl) methyl group, 2- (3-isopropenylphenyl) ethyl group; R ²¹¹ As a group in which is a vinyl group, a 1-methylene-2-propenyl group, a 2-methylene-3-butenyl group; a group in which R ²¹¹ is a phenyl group, 4- (1-Phenylvinyl) phenyl group.

The group represented by the formula (21-V1) is more preferably a vinyl group.

S ²⁰¹ in formula (21) represents a substituted silyl group.

^Examples of the substituted silyl group represented by S ²⁰¹ include a silyl group in which a hydrogen atom bonded to a silicon atom is substituted with a substituent such as an optionally substituted hydrocarbyl group, hydrocarbyloxy group, or substituted amino group. be able to. The substituents bonded to the silicon atom may be the same or different.

（式中、Ｘ^２０１、Ｘ^２０２及びＸ^２０３は、それぞれ独立に、置換アミノ基、又は、置換基を有していてもよいヒドロカルビル基を表し、Ｘ^２０１、Ｘ^２０２及びＸ^２０３の少なくとも１つが置換アミノ基である。） The substituted silyl group represented by S ^201, is preferably a group represented by the following formula (21-S).

(Wherein, X ²⁰¹ , X ²⁰² and X ²⁰³ each independently represent a substituted amino group or a hydrocarbyl group which may have a substituent, wherein at least one of X ²⁰¹ , X ²⁰² and X ²⁰³ is A substituted amino group.)

The hydrocarbyl group which may have a substituent of X ²⁰¹ , X ²⁰² and X ²⁰³ is a hydrocarbyl group which may have at least one selected from the group consisting of an oxygen atom, a nitrogen atom and a silicon atom Can give.

^Examples of the hydrocarbyl group of X ²⁰¹ , X ²⁰² and X ²⁰³ include an alkyl group, an alkenyl group, an alkynyl group, an aryl group and an aralkyl group. Examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, and tert-butyl group. Examples of the alkenyl group include a vinyl group, an allyl group, a 1-propenyl group, and a 1-methylethenyl group. Examples of the alkynyl group include an ethynyl group and a propargyl group. Examples of the aryl group include a phenyl group, a tolyl group, and a xylyl group. Examples of the aralkyl group include a benzyl group. The hydrocarbyl group is preferably an alkyl group.

Examples of the hydrocarbyl group having an oxygen atom of X ²⁰¹ , X ²⁰² and X ²⁰³ include alkoxyalkyl groups such as a methoxymethyl group, a methoxyethyl group, an ethoxymethyl group and an ethoxyethyl group.

Examples of the hydrocarbyl group having a nitrogen atom of X ²⁰¹ , X ²⁰² and X ²⁰³ include dialkylaminoalkyl groups such as dimethylaminomethyl group, dimethylaminoethyl group, diethylaminomethyl group and diethylaminoethyl group.

Examples of the hydrocarbyl group having a silicon atom of X ²⁰¹ , X ²⁰² and X ²⁰³ include trialkylsilylalkyl groups such as a trimethylsilylmethyl group, a trimethylsilylethyl group, a triethylsilylmethyl group, and a triethylsilylethyl group.

The number of carbon atoms of the hydrocarbyl group which may have a substituent of X ²⁰¹ , X ²⁰² and X ²⁰³ is preferably 1 to 10, more preferably 1 to 4.

The hydrocarbyl group which may have a substituent of X ²⁰¹ , X ²⁰² and X ²⁰³ is preferably an alkyl group or an alkoxyalkyl group. The alkyl group is preferably an alkyl group having 1 to 4 carbon atoms, more preferably a methyl group or an ethyl group. The alkoxyalkyl group is preferably an alkoxyalkyl group having 2 to 4 carbon atoms.

（式中、Ｒ^２１５及びＲ^２１６は、それぞれ、ヒドロカルビル基、又は、トリヒドロカルビルシリル基、あるいは、Ｒ^２１５とＲ^２１６とが結合して、窒素原子及び／又は酸素原子をヘテロ原子として有していてもよいヒドロカルビレン基、又は、Ｒ^２１５とＲ^２１６は１つの基であって、窒素原子に二重結合で結合する基を表す。） The substituted amino group for X ²⁰¹ , X ²⁰² and X ²⁰³ is preferably a group represented by the following formula (21-X).

(In the formula, each of R ²¹⁵ and R ²¹⁶ has a hydrocarbyl group, a trihydrocarbyl silyl group, or R ²¹⁵ and R ²¹⁶ bonded to each other, and has a nitrogen atom and / or an oxygen atom as a hetero atom. The hydrocarbylene group, or R ²¹⁵ and R ²¹⁶ may be one group and represents a group bonded to the nitrogen atom with a double bond.

^Examples of the hydrocarbyl group of R ²¹⁵ and R ²¹⁶ include an alkyl group, an alkenyl group, an alkynyl group, an aryl group, and an aralkyl group. Examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, and tert-butyl group. Examples of the alkenyl group include a vinyl group, an allyl group, a 1-propenyl group, and a 1-methylethenyl group. Examples of the alkynyl group include an ethynyl group and a propargyl group. Examples of the aryl group include a phenyl group, a tolyl group, and a xylyl group. Examples of the aralkyl group include a benzyl group.

The number of carbon atoms of the hydrocarbyl group of R ²¹⁵ and R ²¹⁶ is preferably 1 to 10, more preferably 1 to 4, and still more preferably 1 to 2.

The hydrocarbyl group of R ²¹⁵ and R ²¹⁶ is preferably an alkyl group, more preferably a linear alkyl group.

The trihydrocarbyl silyl group R ²¹⁵ and R ^216, may be mentioned trimethylsilyl group, triethylsilyl group, triisopropylsilyl group, a trialkylsilyl group such as tert- butyldimethylsilyl group.

The trihydrocarbyl silyl group R ²¹⁵ and R ^216, preferably a trialkylsilyl group having a carbon number of 3 to 9, more preferably an alkyl group bonded to the silicon atoms of 1 to 3 carbon atoms A trialkylsilyl group which is an alkyl group, and more preferably a trimethylsilyl group.

The hydrocarbylene group optionally having a nitrogen atom and / or an oxygen atom to which R ²¹⁵ and R ²¹⁶ are bonded as a hetero atom includes a hydrocarbylene group, a hydrocarbylene group having a nitrogen atom, and an oxygen atom. And hydrocarbylene groups. Examples of the hydrocarbylene group include an alkylene group such as an ethylene group, a trimethylene group, a tetramethylene group, a pentamethylene group, and a hexamethylene group. As the hydrocarbylene group having a nitrogen atom, a group represented by —CH ₂ CH ₂ —NH—CH ₂ —, a group represented by —CH ₂ CH ₂ —N═CH—, —CH═CH—N A group represented by ═CH— and a group represented by —CH ₂ CH ₂ —NH—CH ₂ CH ₂ — can be exemplified. Examples of the hydrocarbylene group having an oxygen atom include a group represented by —CH ₂ CH ₂ —O—CH ₂ CH ₂ —.

The number of carbon atoms of the hydrocarbylene group which may have a nitrogen atom and / or oxygen atom to which R ²¹⁵ and R ²¹⁶ are bonded as a hetero atom is preferably 2 to 20, more preferably 2 to 7. Yes, more preferably 4-6.

The hydrocarbylene group which may have a nitrogen atom and / or an oxygen atom to which R ²¹⁵ and R ²¹⁶ are bonded as a hetero atom is preferably a hydrocarbylene group, more preferably an alkylene group, A polymethylene group is preferred.

Examples of one group in which R ²¹⁵ and R ²¹⁶ are bonded to the nitrogen atom with a double bond include ethylidene group, propylidene group, butylidene group, 1-methylethylidene group, 1-methylpropylidene group, 1,3-dimethylbutylidene And hydrocarbylidene groups such as groups.

The number of carbon atoms of one group in which R ²¹⁵ and R ²¹⁶ are bonded to the nitrogen atom with a double bond is preferably 2 to 20, and more preferably 2 to 6.

R ²¹⁵ and R ²¹⁶ are preferably an alkyl group, a trialkylsilyl group, an alkylene group in which R ²¹⁵ and R ²¹⁶ are bonded, and more preferably an alkyl group.

Examples of the group represented by the formula (21-X) include an acyclic amino group and a cyclic amino group.

Examples of the acyclic amino group include a dialkylamino group and a bis (trialkylsilyl) amino group. Dialkylamino groups include dimethylamino, diethylamino, di (n-propyl) amino, di (isopropyl) amino, di (n-butyl) amino, di (sec-butyl) amino, di (tert -Butyl) amino group and ethylmethylamino group can be mentioned. Examples of the bis (trialkylsilyl) amino group include a bis (trimethylsilyl) amino group and a bis (t-butyldimethylsilyl) amino group.

Examples of the acyclic amino group include an ethylideneamino group, a 1-methylpropylideneamino group, a 1,3-dimethylbutylideneamino group, a 1-methylethylideneamino group, and a 4-N, N-dimethylaminobenzylideneamino group. You can also give it.

Examples of the cyclic amino group include 1-aziridinyl group, 1-azetidinyl group, 1-pyrrolidinyl group, 1-piperidinyl group, 1-hexamethyleneimino group, 1-heptamethyleneimino group, 1-octamethyleneimino group, 1-decamidine group. Examples thereof include 1-polymethyleneimino groups such as a methyleneimino group and 1-dodecamethyleneimino group. Moreover, 1-pyrrolyl group, 1-pyrazolidinyl group, 1-imidazolidinyl group, 1-pyrazolyl group, 1-imidazolyl group, 4,5-dihydro-1-imidazolyl group, 1-piperazinyl group and morpholino group are exemplified.

The group represented by the formula (21-X) is preferably an acyclic amino group, and more preferably a dialkylamino group. The dialkylamino group is preferably a dimethylamino group, a diethylamino group, a di (n-propyl) amino group, or a di (n-butyl) amino group, and more preferably a dimethylamino group or a diethylamino group.

In formula (21-S), at least one of X ²⁰¹ , X ²⁰² and X ²⁰³ is a substituted amino group, preferably two or more of X ²⁰¹ , X ²⁰² and X ²⁰³ are substituted amino groups, and more Preferably, two of X ²⁰¹ , X ²⁰² and X ²⁰³ are substituted amino groups.

Examples of the compound represented by the formula ^(21), a ^{group V 201} is represented by the formula ^(21-V1), a ^{group S 201} is represented by the formula (21-S), equation (21 V1) ^{R 211} in is a hydrogen atom, a compound which is one of dialkylamino group of ^{X 201, X 202} and ^{X 203} in formula (21-S), it may be mentioned the following compounds.

Compound in which n ^{2 in} formula (21-V1) is 0:
(Dimethylamino) dimethylvinylsilane,
(Diethylamino) dimethylvinylsilane,
(Di-n-propylamino) dimethylvinylsilane,
(Di-n-butylamino) dimethylvinylsilane,
(Dimethylamino) diethylvinylsilane,
(Diethylamino) diethylvinylsilane,
(Di-n-propylamino) diethylvinylsilane,
(Di-n-butylamino) diethylvinylsilane.

Compound in which n ^{2 in} formula (21-V1) is 1:
(Dimethylamino) dimethyl-4-vinylphenylsilane,
(Dimethylamino) dimethyl-3-vinylphenylsilane,
(Diethylamino) dimethyl-4-vinylphenylsilane,
(Diethylamino) dimethyl-3-vinylphenylsilane,
(Di-n-propylamino) dimethyl-4-vinylphenylsilane,
(Di-n-propylamino) dimethyl-3-vinylphenylsilane,
(Di-n-butylamino) dimethyl-4-vinylphenylsilane,
(Di-n-butylamino) dimethyl-3-vinylphenylsilane,
(Dimethylamino) diethyl-4-vinylphenylsilane,
(Dimethylamino) diethyl-3-vinylphenylsilane,
(Diethylamino) diethyl-4-vinylphenylsilane,
(Diethylamino) diethyl-3-vinylphenylsilane,
(Di-n-propylamino) diethyl-4-vinylphenylsilane,
(Di-n-propylamino) diethyl-3-vinylphenylsilane,
(Di-n-butylamino) diethyl-4-vinylphenylsilane,
(Di-n-butylamino) diethyl-3-vinylphenylsilane.

Examples of the compound represented by the formula ^(21), a ^{group V 201} is represented by the formula ^(21-V1), a ^{group S 201} is represented by the formula (21-S), equation (21 V1) ^{R 211} in is a hydrogen atom, a two are dialkylamino group compounds of ^{X 201, X 202} and ^{X 203} in formula (21-S), may be mentioned the following compounds.

Compound in which n ^{2 in} formula (21-V1) is 0:
Bis (dimethylamino) methylvinylsilane,
Bis (diethylamino) methylvinylsilane,
Bis (di-n-propylamino) methylvinylsilane,
Bis (di-n-butylamino) methylvinylsilane,
Bis (dimethylamino) ethylvinylsilane,
Bis (diethylamino) ethylvinylsilane,
Bis (di-n-propylamino) ethylvinylsilane,
Bis (di-n-butylamino) ethylvinylsilane.

Compound in which n ^{2 in} formula (21-V1) is 1:
Bis (dimethylamino) methyl-4-vinylphenylsilane,
Bis (dimethylamino) methyl-3-vinylphenylsilane,
Bis (diethylamino) methyl-4-vinylphenylsilane,
Bis (diethylamino) methyl-3-vinylphenylsilane,
Bis (di-n-propylamino) methyl-4-vinylphenylsilane,
Bis (di-n-propylamino) methyl-3-vinylphenylsilane,
Bis (di-n-butylamino) methyl-4-vinylphenylsilane,
Bis (di-n-butylamino) methyl-3-vinylphenylsilane,
Bis (dimethylamino) ethyl-4-vinylphenylsilane,
Bis (dimethylamino) ethyl-3-vinylphenylsilane,
Bis (diethylamino) ethyl-4-vinylphenylsilane,
Bis (diethylamino) ethyl-3-vinylphenylsilane,
Bis (di-n-propylamino) ethyl-4-vinylphenylsilane,
Bis (di-n-propylamino) ethyl-3-vinylphenylsilane,
Bis (di-n-butylamino) ethyl-4-vinylphenylsilane,
Bis (di-n-butylamino) ethyl-3-vinylphenylsilane.

Examples of the compound represented by the formula ^(21), a ^{group V 201} is represented by the formula ^(21-V1), a ^{group S 201} is represented by the formula (21-S), equation (21 V1) ^{R 211} in is a methyl group, as two are dialkylamino group compounds of ^{X 201, X 202} and ^{X 203} in formula (21-S), it may be mentioned the following compounds.

Compound in which n ^{2 in} formula (21-V1) is 1:
Bis (dimethylamino) methyl-4-isopropenylphenylsilane,
Bis (dimethylamino) methyl-3-isopropenylphenylsilane,
Bis (diethylamino) methyl-4-isopropenylphenylsilane,
Bis (diethylamino) methyl-3-isopropenylphenylsilane,
Bis (di-n-propylamino) methyl-4-isopropenylphenylsilane,
Bis (di-n-propylamino) methyl-3-isopropenylphenylsilane,
Bis (di-n-butylamino) methyl-4-isopropenylphenylsilane,
Bis (di-n-butylamino) methyl-3-isopropenylphenylsilane,
Bis (dimethylamino) ethyl-4-isopropenylphenylsilane,
Bis (dimethylamino) ethyl-3-isopropenylphenylsilane,
Bis (diethylamino) ethyl-4-isopropenylphenylsilane,
Bis (diethylamino) ethyl-3-isopropenylphenylsilane,
Bis (di-n-propylamino) ethyl-4-isopropenylphenylsilane,
Bis (di-n-propylamino) ethyl-3-isopropenylphenylsilane,
Bis (di-n-butylamino) ethyl-4-isopropenylphenylsilane,
Bis (di-n-butylamino) ethyl-3-isopropenylphenylsilane.

Examples of the compound represented by the formula ^(21), a ^{group V 201} is represented by the formula ^(21-V1), a ^{group S 201} is represented by the formula (21-S), equation (21 V1) ^{R 211} in is a vinyl group, as two are dialkylamino group compounds of ^{X 201, X 202} and ^{X 203} in formula (21-S), it may be mentioned the following compounds.

Compound in which n ^{2 in} formula (21-V1) is 0:
Bis (dimethylamino) methyl (1-methylene-2-propenyl) silane,
Bis (diethylamino) methyl (1-methylene-2-propenyl) silane,
Bis (di-n-propylamino) methyl (1-methylene-2-propenyl) silane,
Bis (di-n-butylamino) methyl (1-methylene-2-propenyl) silane,
Bis (dimethylamino) ethyl (1-methylene-2-propenyl) silane,
Bis (diethylamino) ethyl (1-methylene-2-propenyl) silane,
Bis (di-n-propylamino) ethyl (1-methylene-2-propenyl) silane,
Bis (di-n-butylamino) ethyl (1-methylene-2-propenyl) silane.

Examples of the compound represented by the formula ^(21), a ^{group V 201} is represented by the formula ^(21-V1), a ^{group S 201} is represented by the formula (21-S), equation (21 V1) ^{R 211} in is a phenyl group, a 2 is a dialkylamino group compounds of ^{X 201, X 202} and ^{X 203} in formula (21-S), it may be mentioned the following compounds.

Compound in which n ^{2 in} formula (21-V1) is 1:
1- (4-bis (dimethylamino) methylsilyl) -1-phenylethylene,
1- (4-bis (diethylamino) methylsilyl) -1-phenylethylene,
1- (4-bis (di-n-propylamino) methylsilyl) -1-phenylethylene,
1- (4-bis (di-n-butylamino) methylsilyl) -1-phenylethylene,
1- (4-bis (dimethylamino) ethylsilyl) -1-phenylethylene,
1- (4-bis (diethylamino) ethylsilyl) -1-phenylethylene,
1- (4-bis (di-n-propylamino) ethylsilyl) -1-phenylethylene,
1- (4-Bis (di-n-butylamino) ethylsilyl) -1-phenylethylene.

Examples of the compound represented by the formula ^(21), a ^{group V 201} is represented by the formula ^(21-V1), a ^{group S 201} is represented by the formula (21-S), equation (21 V1) ^{R 211} in is a hydrogen atom, a three being dialkylamino group compound of ^{X 201, X 202} and ^{X 203} in formula (21-S), it may be mentioned the following compounds.

Compound in which n ^{2 in} formula (21-V1) is 0:
Tris (dimethylamino) vinylsilane,
Tris (diethylamino) vinylsilane,
Tris (di-n-propylamino) vinylsilane,
Tris (di-n-butylamino) vinylsilane.

Compound in which n ^{2 in} formula (21-V1) is 1:
Tris (dimethylamino) -4-vinylphenylsilane,
Tris (dimethylamino) -3-vinylphenylsilane,
Tris (diethylamino) -4-vinylphenylsilane,
Tris (diethylamino) -3-vinylphenylsilane,
Tris (di-n-propylamino) -4-vinylphenylsilane,
Tris (di-n-propylamino) -3-vinylphenylsilane,
Tris (di-n-butylamino) -4-vinylphenylsilane,
Tris (di-n-butylamino) -3-vinylphenylsilane.

Examples of the compound represented by the formula ^(21), a ^{group V 201} is represented by the formula ^(21-V1), a ^{group S 201} is represented by the formula (21-S), equation (21 V1) ^{R 211} in is a methyl group, a three being dialkylamino group compound of ^{X 201, X 202} and ^{X 203} in formula (21-S), it may be mentioned the following compounds.

Compound in which n ^{2 in} formula (21-V1) is 1:
Tris (dimethylamino) -4-isopropenylphenylsilane,
Tris (dimethylamino) -3-isopropenylphenylsilane,
Tris (diethylamino) -4-isopropenylphenylsilane,
Tris (diethylamino) -3-isopropenylphenylsilane,
Tris (di-n-propylamino) -4-isopropenylphenylsilane,
Tris (di-n-propylamino) -3-isopropenylphenylsilane,
Tris (di-n-butylamino) -4-isopropenylphenylsilane,
Tris (di-n-butylamino) -3-isopropenylphenylsilane.

Examples of the compound represented by the formula ^(21), a ^{group V 201} is represented by the formula ^(21-V1), a ^{group S 201} is represented by the formula (21-S), equation (21 Examples of the compound in which R ^{211 in} V1) is a vinyl group and three of X ²⁰¹ , X ²⁰² and X ²⁰³ in formula (21-S) are dialkylamino groups include the following compounds.

Compound in which n ^{2 in} formula (21-V1) is 0:
Tris (dimethylamino) (1-methylene-2-propenyl) silane,
Tris (diethylamino) (1-methylene-2-propenyl) silane,
Tris (di-n-propylamino) (1-methylene-2-propenyl) silane,
Tris (di-n-butylamino) (1-methylene-2-propenyl) silane.

Examples of the compound represented by the formula ^(21), a ^{group V 201} is represented by the formula ^(21-V1), a ^{group S 201} is represented by the formula (21-S), equation (21 Examples of the compound in which R ^{211 in} V1) is a phenyl group and three of X ²⁰¹ , X ²⁰² and X ²⁰³ in formula (21-S) are dialkylamino groups include the following compounds.

Compound in which n ^{2 in} formula (21-V1) is 1:
1- (4-tris (dimethylamino) silyl) -1-phenylethylene,
1- (4-tris (diethylamino) silyl) -1-phenylethylene,
1- (4-Tris (di-n-propylamino) methylsilyl) -1-phenylethylene, 1- (4-tris (di-n-butylamino) methylsilyl) -1-phenylethylene.

The compound represented by the formula (21) is preferably a compound in which V ²⁰¹ is a group represented by the formula (21-V1) and S ²⁰¹ is a group represented by the formula (21-S). More preferably, a compound in which two of X ²⁰¹ , X ²⁰² and X ²⁰³ in formula (21-S) are dialkylamino groups, and more preferably, R ²¹¹ in formula (21-V1) is is a hydrogen atom, a compound ^{n 2} is 0 in the formula (21-V1). Particularly preferred is a compound in which the remaining one of X ²⁰¹ , X ²⁰² and X ²⁰³ is an alkyl group or an alkoxyalkyl group. Most preferably,
Bis (dimethylamino) methylvinylsilane,
Bis (diethylamino) methylvinylsilane,
Bis (di-n-propylamino) methylvinylsilane,
Bis (di-n-butylamino) methylvinylsilane,
Bis (dimethylamino) ethylvinylsilane,
Bis (diethylamino) ethylvinylsilane,
Bis (di-n-propylamino) ethylvinylsilane,
Bis (di-n-butylamino) ethylvinylsilane.

V ²⁰² in the formula (22) represents a hydrocarbyl group having a polymerizable carbon-carbon double bond.

V ²⁰² is preferably a group represented by the following formula (22-V).

（式中、ｍ^２は０又は１であり、Ｒ^２２１、Ｒ^２２３及びＲ^２２４は、それぞれ独立に水素原子又はヒドロカルビル基を表し、Ｒ^２２２はヒドロカルビレン基を表す。）

(In the formula, m ² is 0 or 1, R ²²¹ , R ²²³ and R ²²⁴ each independently represent a hydrogen atom or a hydrocarbyl group, and R ²²² represents a hydrocarbylene group.)

In the formula (22-V), m ² represents 0 or 1.

^Examples of the hydrocarbyl group of R ²²¹ , R ²²³ and R ²²⁴ include an alkyl group, an alkenyl group, and an aryl group. Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, and a tert-butyl group, and a methyl group is preferable. Examples of the alkenyl group include a vinyl group, an allyl group, a 1-propenyl group, and a 1-methylethenyl group, and a vinyl group is preferable. Examples of the aryl group include a phenyl group, a methylphenyl group, and an ethylphenyl group, and a phenyl group is preferable.

R ²²¹ , R ²²³ and R ²²⁴ are preferably a hydrogen atom, a methyl group, a vinyl group or a phenyl group, more preferably a hydrogen atom.

^Examples of the hydrocarbylene group for R ²²² include an alkylene group, an arylene group, and a group in which an arylene group and an alkylene group are bonded.

Examples of the alkylene group include a methylene group, an ethylene group, and a trimethylene group. Preferably, it is a methylene group or an ethylene group. Examples of the arylene group include a phenylene group, a naphthylene group, and a biphenylene group. A phenylene group is preferred. More preferred are a para-phenylene group and a meta-phenylene group.

Examples of the group in which an arylene group and an alkylene group are bonded include a group in which a phenylene group and an alkylene group are bonded, a group in which a naphthylene group and an alkylene group are bonded, and a group in which a biphenylene group and an alkylene group are bonded. .
Examples of a group and arylene group and an alkylene group is bonded, the carbon atom to which R ²²¹ in the formula (2-V) is attached, it is preferable that the carbon atoms of the arylene group in the group is attached.

In a group in which a phenylene group and an alkylene group are bonded (phenylene-alkylene group (for example, a group represented by the following formula (22-R))), the position of a carbon atom on a benzene ring from which a hydrogen atom is removed and Depending on the position of the carbon atom on the benzene ring to which the alkylene group is bonded, a para-phenylene-alkylene group (for example, a group represented by the following formula (22-Ra)), a meta-phenylene-alkylene group (for example, A group represented by the following formula (22-Rb)), and an ortho-phenylene-alkylene group (for example, a group represented by the following formula (22-Rc)).

（式中、ｈ^２は１〜１０の整数を表し、（ＣＨ_２）_ｈ２はベンゼン環上の置換基である。）

(In the formula, h ² represents an integer of 1 to 10, and (CH ₂ ) _{h 2} is a substituent on the benzene ring.)

（式中、ｉ^２、ｊ^２、ｋ^２は、それぞれ、１〜１０の整数を表す。）

^{(Wherein, i 2, j 2, k} 2 each represent an integer of 1 to 10.)

^{K 2} of the formula ^{h 2} of (22-R), ^{i 2} of the formula (22-Ra), ^{j 2} of the formula (22-Rb), formula (22-Rc) is preferably 1 to 5, more Preferably it is 1-2, More preferably, it is 1.

The group in which an arylene group and an alkylene group are bonded is preferably a group in which a phenylene group and an alkylene group are bonded, and more preferably a group represented by the above formula (22-Ra) or the above formula (22 -Rb), more preferably a para-phenylene-methylene group (a group represented by the formula (22-Ra) where i ² = 1), a meta-phenylene-methylene group (j ² = 1, a group represented by the formula (22-Rb)), a para-phenylene-ethylene group (a group represented by the formula (22-Ra) where i ² = 2), a meta-phenylene-ethylene group ( a group represented by formula (22-Rb) in which j ² = 2), and particularly preferably a para-phenylene-methylene group (a group represented by formula (22-Ra) in which i ² = 1)). , meta - methylene group ^(j 2 = 1 - phenylene That is a radical represented by (22-Rb)).

Examples of the group represented by the formula (22-V) include the following groups.

Examples of the group in which R ²²¹ , R ^223, and R ²²⁴ are hydrogen atoms include a vinyl group, vinylmethyl group, vinylethyl group, 4-vinylphenyl group, 3-vinylphenyl group, (4-vinylphenyl) methyl group, 2- ( 4-vinylphenyl) ethyl group, (3-vinylphenyl) methyl group, 2- (3-vinylphenyl) ethyl group and the like can be mentioned.

^Examples of the group in which R ²²¹ is a methyl group and R ²²³ and R ²²⁴ are hydrogen atoms include an isopropenyl group, a methallyl group, a 4-isopropenylphenyl group, a 3-isopropenylphenyl group, and (4-isopropenylphenyl) methyl. Group, 2- (4-isopropenylphenyl) ethyl group, (3-isopropenylphenyl) methyl group, 2- (3-isopropenylphenyl) ethyl group and the like.

^Examples of the group in which R ²²¹ is a vinyl group and R ²³ and R ²⁴ are hydrogen atoms include a 1-methylene-2-propenyl group and a 2-methylene-3-butenyl group.

^Examples of the group in which R ²²¹ is a phenyl group and R ²³ and R ²⁴ are hydrogen atoms include 4- (1-phenylvinyl) phenyl group, 3- (1-phenylvinyl) phenyl group, and 2- (1-phenylvinyl). ) A phenyl group can be mentioned.

^Examples of the group in which R ²²¹ is a hydrogen atom, R ²²³ is a methyl group, and R ²²⁴ is a hydrogen atom include a 1-propenyl group, a crotyl group, a 4- (1-propenyl) phenyl group, and a 4- (1-propenyl group). ) Phenylmethyl group, 2- {4- (1-propenyl) phenyl} ethyl group, 3- (1-propenyl) phenyl group, 3- (1-propenyl) phenylmethyl group, 2- {3- (1-propenyl) ) Phenyl} ethyl group and the like.

（式中、Ｒ^２２１は水素原子又はヒドロカルビル基を表し、ｍ^２は０又は１であり、Ｒ^２２２はヒドロカルビレン基を表す。） The group represented by the formula (22-V) is preferably a group represented by the following formula (22-V1).

(Wherein R ²²¹ represents a hydrogen atom or a hydrocarbyl group, m ² represents 0 or 1, and R ²²² represents a hydrocarbylene group.)

The group represented by the formula (22-V1) is preferably a group in which R ²²¹ is a hydrogen atom, such as a vinyl group, 4-vinylphenyl group, 3-vinylphenyl group, (4-vinylphenyl) methyl group, 2 -(4-vinylphenyl) ethyl group, (3-vinylphenyl) methyl group, 2- (3-vinylphenyl) ethyl group; R ²²¹ is a methyl group, such as 4-isopropenylphenyl group, 3-iso Propenylphenyl group, (4-isopropenylphenyl) methyl group, 2- (4-isopropenylphenyl) ethyl group, (3-isopropenylphenyl) methyl group, 2- (3-isopropenylphenyl) ethyl group; R ²²¹ As a group in which R is a vinyl group, a 1-methylene-2-propenyl group, a 2-methylene-3-butenyl group; a group in which R ²²¹ is a phenyl group, 4- (1-Phenylvinyl) phenyl group.

The group represented by the formula (22-V1) is more preferably a vinyl group, (4-vinylphenyl) ethyl group, or (3-vinylphenyl) ethyl group in which ^R221 is a hydrogen atom.

In formula (22), A ²⁰² represents a substituted amino group or a nitrogen-containing heterocyclic group.

（式中、Ｒ^２２５及びＲ^２２６は、それぞれ、ヒドロカルビル基、又は、トリヒドロカルビルシリル基、あるいは、Ｒ^２２５とＲ^２２６とが結合して、窒素原子及び／又は酸素原子をヘテロ原子として有していてもよいヒドロカルビレン基、又は、Ｒ^２２５とＲ^２２６は１つの基であって、窒素原子に二重結合で結合する基を表す。） The substituted amino group for A ²⁰² is preferably a group represented by the following formula (22-A).

(In the formula, each of R ²²⁵ and R ²²⁶ has a hydrocarbyl group, a trihydrocarbyl silyl group, or R ²²⁵ and R ²²⁶ bonded to each other, and has a nitrogen atom and / or an oxygen atom as a hetero atom. The hydrocarbylene group that may be substituted, or R ²²⁵ and R ²²⁶ are one group and represent a group bonded to the nitrogen atom with a double bond.)

^Examples of the hydrocarbyl group of R ²²⁵ and R ²²⁶ include an alkyl group, an alkenyl group, an alkynyl group, an aryl group, and an aralkyl group. Examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, and tert-butyl group. Examples of the alkenyl group include a vinyl group, an allyl group, a 1-propenyl group, and a 1-methylethenyl group. Examples of the alkynyl group include an ethynyl group and a propargyl group. Examples of the aryl group include a phenyl group, a tolyl group, and a xylyl group. Examples of the aralkyl group include a benzyl group.

The number of carbon atoms of the hydrocarbyl group of R ²²⁵ and R ²²⁶ is preferably 1 to 10, more preferably 1 to 4, and still more preferably 1 to 2.

The hydrocarbyl group of R ²²⁵ and R ²²⁶ is preferably an alkyl group or an alkenyl group, more preferably an alkyl group, and still more preferably a linear alkyl group.

The trihydrocarbyl silyl group R ²²⁵ and R ^226, may be mentioned trimethylsilyl group, triethylsilyl group, triisopropylsilyl group, a trialkylsilyl group such as tert- butyldimethylsilyl group.

The trihydrocarbyl silyl group R ²²⁵ and R ^226, preferably a trialkylsilyl group having a carbon number of 3 to 9, more preferably an alkyl group bonded to the silicon atoms of 1 to 4 carbon atoms A trialkylsilyl group which is an alkyl group, and more preferably a trimethylsilyl group.

The hydrocarbylene group optionally having a nitrogen atom and / or an oxygen atom to which R ²²⁵ and R ²²⁶ are bonded as a hetero atom includes a hydrocarbylene group, a hydrocarbylene group having a nitrogen atom, and an oxygen atom. And hydrocarbylene groups. Examples of the hydrocarbylene group include an alkylene group such as an ethylene group, a trimethylene group, a tetramethylene group, a pentamethylene group, and a hexamethylene group. As the hydrocarbylene group having a nitrogen atom, a group represented by —CH ₂ CH ₂ —NH—CH ₂ —, a group represented by —CH ₂ CH ₂ —N═CH—, —CH═CH—N A group represented by ═CH— and a group represented by —CH ₂ CH ₂ —NH—CH ₂ CH ₂ — can be exemplified. Examples of the hydrocarbylene group having an oxygen atom include a group represented by —CH ₂ CH ₂ —O—CH ₂ CH ₂ —.

The number of carbon atoms of the hydrocarbylene group which may have a nitrogen atom and / or oxygen atom to which R ²²⁵ and R ²²⁶ are bonded as a hetero atom is preferably 2 to 20, more preferably 2 to 7. Yes, more preferably 4-6.

The hydrocarbylene group which may have a nitrogen atom and / or an oxygen atom to which R ²²⁵ and R ²²⁶ are bonded as a hetero atom is preferably a hydrocarbylene group, more preferably an alkylene group, A polymethylene group is preferred.

Examples of one group in which R ²²⁵ and R ²²⁶ are bonded to the nitrogen atom with a double bond include ethylidene group, propylidene group, butylidene group, 1-methylethylidene group, 1-methylpropylidene group, 1,3-dimethylbutylidene And hydrocarbylidene groups such as groups.

The number of carbon atoms of one group in which R ²²⁵ and R ²²⁶ are bonded to the nitrogen atom with a double bond is preferably 2 to 20, and more preferably 2 to 6.

R ²²⁵ and R ²²⁶ are preferably a hydrocarbyl group, a trihydrocarbyl silyl group, and a hydrocarbylene group in which R ²²⁵ and R ²²⁶ are bonded.

Examples of the group represented by the formula (22-A) include an acyclic amino group and a cyclic amino group.

Examples of the acyclic amino group include a dialkylamino group and a bis (trialkylsilyl) amino group. Dialkylamino groups include dimethylamino, diethylamino, di (n-propyl) amino, di (isopropyl) amino, di (n-butyl) amino, di (sec-butyl) amino, di (tert -Butyl) amino group and ethylmethylamino group can be mentioned. Examples of the bis (trialkylsilyl) amino group include a bis (trimethylsilyl) amino group and a bis (tert-butyldimethylsilyl) amino group.

Examples of the acyclic amino group include an ethylideneamino group, a 1-methylpropylideneamino group, a 1,3-dimethylbutylideneamino group, a 1-methylethylideneamino group, and a 4-N, N-dimethylaminobenzylideneamino group. Can do.

Examples of the cyclic amino group include 1-aziridinyl group, 1-azetidinyl group, 1-pyrrolidinyl group, 1-piperidinyl group, 1-hexamethyleneimino group, 1-imidazolyl group, 4,5-dihydro-1-imidazolyl group, 1 Examples include -pyrrolyl group, 1-pyrazolyl group, 1-imidazolidinyl group, 1-piperazinyl group, and morpholino group.

The group represented by the formula (22-A) is preferably a group in which R ²²⁵ and R ²²⁶ are hydrocarbyl groups, a group in which R ²²⁵ and R ²²⁶ are trihydrocarbyl silyl groups, and R ²²⁵ and R ²²⁶ are bonded. Group which is a hydrocarbylene group. More preferably, R ²²⁵ and R ²²⁶ are a group that is a linear alkyl group, R ²²⁵ and R ²²⁶ are a group that is a trialkylsilyl group, and a group that is a polymethylene group to which R ²²⁵ and R ²²⁶ are bonded.

The group represented by the formula (22-A) is more preferably a dimethylamino group, a diethylamino group, a di (n-propyl) amino group, a di (n-butyl) amino group, a bis (trimethylsilyl) amino group, A bis (tert-butyldimethylsilyl) amino group, a 1-pyrrolidinyl group, a 1-piperidinyl group, and a 1-hexamethyleneimino group, particularly preferably a 1-pyrrolidinyl group.

^Examples of the nitrogen-containing heterocyclic group represented by A ²⁰² include a nitrogen-containing aliphatic heterocyclic group and a nitrogen-containing aromatic heterocyclic group. In the present specification, a nitrogen-containing aliphatic heterocyclic group represents a group obtained by removing one hydrogen atom from a carbon atom of a heterocyclic ring of a compound having a nitrogen-containing aliphatic heterocyclic ring. Represents an aliphatic heterocycle having a nitrogen atom as a heteroatom. The nitrogen-containing aromatic heterocyclic group represents a group obtained by removing one hydrogen atom from a carbon atom of a heterocyclic ring of a compound having a nitrogen-containing aromatic heterocyclic ring, and the nitrogen-containing aromatic heterocyclic ring constitutes a ring. An aromatic heterocyclic ring having a nitrogen atom as a hetero atom is represented.

^Examples of the nitrogen-containing aliphatic heterocyclic group represented by A ²⁰² include a group having only a nitrogen atom as a hetero atom constituting a ring, a group having a nitrogen atom and an oxygen atom as a hetero atom constituting a ring, and a hetero atom constituting a ring. Examples thereof include a group having a nitrogen atom and a sulfur atom.

The nitrogen-containing aliphatic heterocyclic group having only a nitrogen atom as a hetero atom constituting the ring includes a group having an aziridine ring, a group having an azetidine ring, a group having a pyrrolidine ring, a group having a piperidine ring, a hexamethyleneimine ring , A group having an imidazolidine ring, a group having a piperazine ring, a group having a pyrazolidine ring, and the like.

Examples of the group having an aziridine ring include an N-alkyl-2-aziridinyl group.
Examples of the group having an azetidine ring include an N-alkyl-2-azetidinyl group and an N-alkyl-3-azetidinyl group.
Examples of the group having a pyrrolidine ring include an N-alkyl-2-pyrrolidinyl group and an N-alkyl-3-pyrrolidinyl group.
Examples of the group having a piperidine ring include an N-alkyl-2-piperidinyl group, an N-alkyl-3-piperidinyl group, and an N-alkyl-4-piperidinyl group.
Examples of the group having a hexamethyleneimine ring include an N-alkyl-2-hexamethyleneimino group, an N-alkyl-3-hexamethyleneimino group, and an N-alkyl-4-hexamethyleneimino group.
Examples of the group having an imidazolidine ring include a 1,3-dialkyl-2-imidazolidyl group and a 1,3-dialkyl-4-imidazolidyl group.
Examples of the group having a piperazine ring include a 1,4-dialkyl-2-piperazinyl group.
Examples of the group having a pyrazolidine ring include a 1,2-dialkyl-3-pyrazolidyl group and a 1,2-dialkyl-4-pyrazolidyl group.

Examples of the nitrogen-containing aliphatic heterocyclic group having a nitrogen atom and an oxygen atom as a hetero atom constituting the ring include a group having a morpholine ring and a group having an isoxazolidine ring.

Examples of the group having a morpholine ring include an N-alkyl-2-morpholino group and an N-alkyl-3-morpholino group.
Examples of the group having an isoxazolidine ring include an N-alkyl-3-isoxazolidinyl group, an N-alkyl-4-isoxazolidinyl group, and an N-alkyl-5-isoxazolidinyl group. Can do.

Examples of the nitrogen-containing aliphatic heterocyclic group having a nitrogen atom and a sulfur atom as hetero atoms constituting the ring include a group having a thiomorpholine ring and a group having an isothiazolidine ring.

Examples of the group having a thiomorpholine ring include an N-alkyl-2-thiomorpholino group and an N-alkyl-3-thiomorpholino group.
Examples of the group having an isothiazolidine ring include an N-alkyl-3-isothiazolidinyl group, an N-alkyl-4-isothiazolidinyl group, and an N-alkyl-5-isothiazolidinyl group.

The nitrogen-containing aliphatic heterocyclic group represented by A ²⁰² is preferably a group having only a nitrogen atom as a hetero atom constituting the ring. The number of carbon atoms in the nitrogen-containing aliphatic heterocyclic group is preferably 4-10.

As the nitrogen-containing aromatic heterocyclic group represented by A ²⁰² , a group having only a nitrogen atom as a hetero atom constituting a ring, a group having a nitrogen atom and an oxygen atom as a hetero atom constituting a ring, and a hetero atom constituting a ring Examples thereof include a group having a nitrogen atom and a sulfur atom.

The nitrogen-containing aromatic heterocyclic group having only a nitrogen atom as a hetero atom constituting the ring includes a group having a pyrrole ring, a group having an imidazole ring, a group having a pyrazole ring, a group having a pyridine ring, and a pyridazine ring. A group having a pyrimidine ring, a group having a pyrazine ring, a group having a quinoline ring, a group having an isoquinoline ring, a group having a cinnoline ring, a group having a quinazoline ring, a group having a phthalazine ring, and the like.

Examples of the group having a pyrrole ring include a 2-pyrrolyl group, a 3-pyrrolyl group, a 2- (N-methylpyrrolyl) group, and a 3- (N-methylpyrrolyl) group.
Examples of the group having an imidazole ring include 2-imidazolyl group, 4-imidazolyl group, 5-imidazolyl group, 2- (N-methylimidazolyl) group, 4- (N-methylimidazolyl) group, and 5- (N-methylimidazolyl). ) Group.
Examples of the group having a pyrazole ring include 3-pyrazolyl group, 4-pyrazolyl group, 5-pyrazolyl group, 3- (N-methylpyrazolyl) group, 4- (N-methylpyrazolyl) group, and 5- (N-methylpyrazolyl). ) Group.
Examples of the group having a pyridine ring include a 2-pyridyl group, a 3-pyridyl group, and a 4-pyridyl group.
Examples of the group having a pyridazine ring include a 3-pyridazyl group and a 4-pyridazyl group.
Examples of the group having a pyrimidine ring include a 2-pyrimidyl group, a 4-pyrimidyl group, and a 5-pyrimidyl group.
Examples of the group having a pyrazine ring include a 2-pyrazyl group.
Examples of the group having a quinoline ring include a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 5-quinolyl group, a 6-quinolyl group, a 7-quinolyl group, and an 8-quinolyl group.
Examples of the group having an isoquinoline ring include a 1-isoquinolyl group, a 3-isoquinolyl group, a 4-isoquinolyl group, a 5-isoquinolyl group, a 6-isoquinolyl group, a 7-isoquinolyl group, and an 8-isoquinolyl group.
Examples of the group having a cinnoline ring include a 3-cinnolinyl group, a 4-cinnolinyl group, a 5-cinnolinyl group, a 6-cinnolinyl group, a 7-cinnolinyl group, and an 8-cinnolinyl group.
Examples of the group having a quinazoline ring include a 2-quinazolinyl group, a 4-quinazolinyl group, a 5-quinazolinyl group, a 6-quinazolinyl group, a 7-quinazolinyl group, and an 8-quinazolinyl group.
Examples of the group having a phthalazine ring include a 1-phthalazinyl group, a 5-phthalazinyl group, and a 6-phthalazinyl group.
The nitrogen-containing aromatic heterocyclic group having only a nitrogen atom as a hetero atom constituting the ring is preferably a group having an imidazole ring, a group having a pyridine ring, or a group having a quinoline ring.

Examples of the nitrogen-containing aromatic heterocyclic group having a nitrogen atom and an oxygen atom as hetero atoms constituting the ring include a group having an oxazole ring and a group having an isoxazole ring.

Examples of the group having an oxazole ring include a 2-oxazolyl group, a 4-oxazolyl group, and a 5-oxazolyl group.
Examples of the group having an isoxazole ring include a 3-isoxazolyl group, a 4-isoxazolyl group, and a 5-isoxazolyl group.
The nitrogen-containing aromatic heterocyclic group having a nitrogen atom and an oxygen atom as hetero atoms constituting the ring is preferably a group having an oxazole ring.

Examples of the nitrogen-containing aromatic heterocyclic group having a nitrogen atom and a sulfur atom as the hetero atoms constituting the ring include a group having a thiazole ring, a group having an isothiazole ring, and the like.

Examples of the group having a thiazole ring include a 2-thiazolyl group, a 4-thiazolyl group, and a 5-thiazolyl group.
Examples of the group having an isothiazole ring include a 3-isothiazolyl group, a 4-isothiazolyl group, and a 5-isothiazolyl group.
The nitrogen-containing aromatic heterocyclic group having a nitrogen atom and a sulfur atom as a hetero atom constituting the ring is preferably a group having a thiazole ring.

The nitrogen-containing aromatic heterocyclic group represented by A ²⁰² is preferably a nitrogen-containing aromatic heterocyclic group having only a nitrogen atom as a hetero atom constituting the ring, more preferably a group having an imidazole ring or a pyridine ring. And a group having a quinoline ring, more preferably a group having a pyridine ring.

As a compound represented by the formula (22), V ²⁰² is a group represented by the formula (22-V1), R ²²¹ in the formula (22-V1) is a hydrogen atom, and m ² is 0. In addition, examples of the compound in which A ²⁰² is a substituted amino group include the following compounds.

1-vinylpyrrolidine,
1-vinyl piperidine,
1-vinylhexamethyleneimine,
1-vinyl piperazine,
1-vinyl pyrrole,
1-vinylimidazole,
1-vinylpyrazole,
1-Vinylquinoline.

As a compound represented by the formula (22), V ²⁰² is a group represented by the formula (22-V1), R ²²¹ in the formula (22-V1) is a hydrogen atom, and m ² is 1. In addition, examples of the compound in which R ²²² is a phenylene group and A ²⁰² is a substituted amino group include the following compounds.

4-N, N-dimethylaminostyrene,
4-N, N-diethylaminostyrene,
4-N, N-di-n-propylaminostyrene,
4-N, N-di-n-butylaminostyrene,
4-N, N-diallylaminostyrene,
4-N, N-bis (trimethylsilyl) aminostyrene,
4-N, N-bis (tert-butyldimethylsilyl) aminostyrene,
4- (1-aziridinyl) styrene,
4- (1-pyrrolidinyl) styrene,
4- (1-piperidinyl) styrene,
4- (1-hexamethyleneimino) styrene,
3-N, N-dimethylaminostyrene,
3-N, N-diethylaminostyrene,
3-N, N-di-n-propylaminostyrene,
3-N, N-di-n-butylaminostyrene,
3-N, N-diallylaminostyrene,
3-N, N-bis (trimethylsilyl) aminostyrene,
3-N, N-bis (tert-butyldimethylsilyl) aminostyrene,
3- (1-aziridinyl) styrene,
3- (1-pyrrolidinyl) styrene,
3- (1-piperidinyl) styrene,
3- (1-Hexamethyleneimino) styrene.

As a compound represented by the formula (22), V ²⁰² is a group represented by the formula (22-V1), R ²²¹ in the formula (22-V1) is a hydrogen atom, and m ² is 1. In addition, examples of the compound in which R ²²² is a group represented by the formula (22-Ra) and A ²⁰² is a substituted amino group include the following compounds.

Compound ^{i 2} of the formula (22-Ra) is 1:
4-N, N-dimethylaminomethylstyrene,
4-N, N-diethylaminomethylstyrene,
4-N, N-di-n-propylaminomethylstyrene,
4-N, N-di-n-butylaminomethylstyrene,
4-N, N-diallylaminomethylstyrene,
4-N, N-bis (trimethylsilyl) aminomethylstyrene,
4-N, N-bis (tert-butyldimethylsilyl) aminomethylstyrene,
4- (1-aziridinyl) methylstyrene,
4- (1-pyrrolidinyl) methylstyrene,
4- (1-piperidinyl) methylstyrene,
4- (1-Hexamethyleneimino) methylstyrene.

Compound ^{i 2} of the formula (22-Ra) is 2:
4-N, N-dimethylaminoethylstyrene,
4-N, N-diethylaminoethylstyrene,
4-N, N-di-n-propylaminoethylstyrene,
4-N, N-di-n-butylaminoethylstyrene,
4-N, N-diallylaminoethylstyrene,
4-N, N-bis (trimethylsilyl) aminoethylstyrene,
4-N, N-bis (tert-butyldimethylsilyl) aminoethylstyrene,
4- (1-aziridinyl) ethylstyrene,
4- (1-piperidinyl) ethylstyrene,
4- (1-pyrrolidinyl) ethylstyrene,
4- (1-Hexamethyleneimino) ethylstyrene.

As a compound represented by the formula (22), V ²⁰² is a group represented by the formula (22-V1), R ²²¹ in the formula (22-V1) is a hydrogen atom, and m ² is 1. In addition, examples of the compound in which R ²²² is a group represented by the formula (22-Rb) and A ²⁰² is a substituted amino group include the following compounds.

A compound in which j ^{2 of} formula (22-Rb) is 1:
3-N, N-dimethylaminomethylstyrene,
3-N, N-diethylaminomethylstyrene,
3-N, N-di-n-propylaminomethylstyrene,
3-N, N-di-n-butylaminomethylstyrene,
3-N, N-diallylaminomethylstyrene,
3-N, N-bis (trimethylsilyl) aminomethylstyrene,
3-N, N-bis (tert-butyldimethylsilyl) aminomethylstyrene,
3- (1-aziridinyl) methylstyrene,
3- (1-pyrrolidinyl) methylstyrene,
3- (1-piperidinyl) methylstyrene,
3- (1-Hexamethyleneimino) methylstyrene.

Compound ^{j 2} of the formula (22-Rb) is 2:
3-N, N-dimethylaminoethylstyrene,
3-N, N-diethylaminoethylstyrene,
3-N, N-di-n-propylaminoethylstyrene,
3-N, N-di-n-butylaminoethylstyrene,
3-N, N-diallylaminoethylstyrene,
3-N, N-bis (trimethylsilyl) aminoethylstyrene,
3-N, N-bis (tert-butyldimethylsilyl) aminoethylstyrene,
3- (1-aziridinyl) ethylstyrene,
3- (1-piperidinyl) ethylstyrene,
3- (1-pyrrolidinyl) ethylstyrene,
3- (1-Hexamethyleneimino) ethylstyrene.

As a compound represented by the formula (22), V ²⁰² is a group represented by the formula (22-V1), R ²²¹ in the formula (22-V1) is a methyl group, and m ² is 0. In addition, examples of the compound in which A ²⁰² is a substituted amino group include the following compounds.

1-isopropenylpyrrolidine,
1-isopropenyl piperidine,
1-isopropenyl hexamethyleneimine,
1-isopropenyl piperazine,
1-isopropenyl pyrrole,
1-isopropenylimidazole,
1-isopropenylpyrazole,
Isopropenyl quinoline.

As a compound represented by the formula (22), V ²⁰² is a group represented by the formula (22-V1), R ²²¹ in the formula (22-V1) is a methyl group, and m ² is 1. In addition, examples of the compound in which R ²²² is a phenylene group and A ²⁰² is a substituted amino group include the following compounds.

4-N, N-dimethylaminoisopropenylbenzene,
4-N, N-diethylaminoisopropenylbenzene,
4-N, N-di-n-propylaminoisopropenylbenzene,
4-N, N-di-n-butylaminoisopropenylbenzene,
4-N, N-diallylaminoisopropenylbenzene,
4-N, N-bis (trimethylsilyl) aminoisopropenylbenzene,
4-N, N-bis (tert-butyldimethylsilyl) aminoisopropenylbenzene, 4- (1-aziridinyl) isopropenylbenzene,
4- (1-pyrrolidinyl) isopropenylbenzene,
4- (1-piperidinyl) isopropenylbenzene,
4- (1-hexamethyleneimino) isopropenylbenzene,
3-N, N-dimethylaminoisopropenylbenzene,
3-N, N-diethylaminoisopropenylbenzene,
3-N, N-di-n-propylaminoisopropenylbenzene,
3-N, N-di-n-butylaminoisopropenylbenzene,
3-N, N-diallylaminoisopropenylbenzene,
3-N, N-bis (trimethylsilyl) aminoisopropenylbenzene,
3-N, N-bis (tert-butyldimethylsilyl) aminoisopropenylbenzene, 3- (1-aziridinyl) isopropenylbenzene,
3- (1-pyrrolidinyl) isopropenylbenzene,
3- (1-piperidinyl) isopropenylbenzene,
3- (1-Hexamethyleneimino) isopropenylbenzene.

As a compound represented by the formula (22), V ²⁰² is a group represented by the formula (22-V1), R ²²¹ in the formula (22-V1) is a methyl group, and m ² is 1. In addition, examples of the compound in which R ²²² is a group represented by the formula (22-Ra) and A ²⁰² is a substituted amino group include the following compounds.

Compound ^{i 2} of the formula (22-Ra) is 1:
4-N, N-dimethylaminomethylisopropenylbenzene,
4-N, N-diethylaminomethylisopropenylbenzene,
4-N, N-di-n-propylaminomethylisopropenylbenzene,
4-N, N-di-n-butylaminomethylisopropenylbenzene,
4-N, N-diallylaminomethylisopropenylbenzene,
4-N, N-bis (trimethylsilyl) aminomethylisopropenylbenzene,
4-N, N-bis (tert-butyldimethylsilyl) aminomethylisopropenylbenzene,
4- (1-aziridinyl) methylisopropenylbenzene,
4- (1-pyrrolidinyl) methylisopropenylbenzene,
4- (1-piperidinyl) methyl isopropenylbenzene,
4- (1-Hexamethyleneimino) methylisopropenylbenzene.

Compound ^{i 2} of the formula (22-Ra) is 2:
4-N, N-dimethylaminoethylisopropenylbenzene,
4-N, N-diethylaminoethylisopropenylbenzene,
4-N, N-di-n-propylaminoethylisopropenylbenzene,
4-N, N-di-n-butylaminoethylisopropenylbenzene,
4-N, N-diallylaminoethyl isopropenylbenzene,
4-N, N-bis (trimethylsilyl) aminoethylisopropenylbenzene,
4-N, N-bis (tert-butyldimethylsilyl) aminoethylisopropenylbenzene,
4- (1-aziridinyl) ethyl isopropenylbenzene,
4- (1-pyrrolidinyl) ethyl isopropenylbenzene,
4- (1-piperidinyl) ethyl isopropenylbenzene,
4- (1-Hexamethyleneimino) ethyl isopropenylbenzene.

As a compound represented by the formula (22), V ²⁰² is a group represented by the formula (22-V1), R ²²¹ in the formula (22-V1) is a methyl group, and m ² is 1. In addition, examples of the compound in which R ²²² is a group represented by the formula (22-Rb) and A ²⁰² is a substituted amino group include the following compounds.

A compound in which j ^{2 of} formula (22-Rb) is 1:
3-N, N-dimethylaminomethylisopropenylbenzene,
3-N, N-diethylaminomethylisopropenylbenzene,
3-N, N-di-n-propylaminomethylisopropenylbenzene,
3-N, N-di-n-butylaminomethylisopropenylbenzene,
3-N, N-diallylaminomethylisopropenylbenzene,
3-N, N-bis (trimethylsilyl) aminomethylisopropenylbenzene,
3-N, N-bis (tert-butyldimethylsilyl) aminomethylisopropenylbenzene,
3- (1-aziridinyl) methyl isopropenylbenzene,
3- (1-pyrrolidinyl) methylisopropenylbenzene,
3- (1-piperidinyl) methylisopropenylbenzene,
3- (1-Hexamethyleneimino) methylisopropenylbenzene.

Compound ^{j 2} of the formula (22-Rb) is 2:
3-N, N-dimethylaminoethylisopropenylbenzene,
3-N, N-diethylaminoethylisopropenylbenzene,
3-N, N-di-n-propylaminoethylisopropenylbenzene,
3-N, N-di-n-butylaminoethyl isopropenylbenzene,
3-N, N-diallylaminoethylisopropenylbenzene,
3-N, N-bis (trimethylsilyl) aminoethylisopropenylbenzene,
3-N, N-bis (tert-butyldimethylsilyl) aminoethylisopropenylbenzene,
3- (1-aziridinyl) ethyl isopropenylbenzene,
3- (1-pyrrolidinyl) ethyl isopropenylbenzene,
3- (1-piperidinyl) ethyl isopropenylbenzene,
3- (1-Hexamethyleneimino) ethyl isopropenylbenzene.

As a compound represented by the formula (22), V ²⁰² is a group represented by the formula (22-V1), R ²²¹ in the formula (22-V1) is a vinyl group, and m ² is 0. In addition, examples of the compound in which A ²⁰² is a substituted amino group include the following compounds.

2-N, N-dimethylamino-1,3-butadiene,
2-N, N-diethylamino-1,3-butadiene,
2-N, N-di-n-propylamino-1,3-butadiene,
2-N, N-di-n-butylamino-1,3-butadiene,
2-N, N-diallylamino-1,3-butadiene,
2-N, N-bis (trimethylsilyl) amino-1,3-butadiene,
2-N, N-bis (tert-butyldimethylsilyl) amino-1,3-butadiene,
2- (1-aziridinyl) -1,3-butadiene,
2- (1-pyrrolidinyl) -1,3-butadiene,
2- (1-piperidinyl) -1,3-butadiene,
2- (1-hexamethyleneimino) -1,3-butadiene,
2- (1-pyrrolyl) -1,3-butadiene,
2- (1-imidazolyl) -1,3-butadiene,
2- (1-Pyrazolyl) -1,3-butadiene.

As a compound represented by the formula (22), V ²⁰² is a group represented by the formula (22-V1), R ²²¹ in the formula (22-V1) is a vinyl group, and m ² is 1. In addition, examples of the compound in which R ²²² is an alkylene group and A ²⁰² is a substituted amino group include the following compounds.

Compound in which R ²²² is a methylene group:
2-N, N-dimethylaminomethyl-1,3-butadiene,
2-N, N-diethylaminomethyl-1,3-butadiene,
2-N, N-di-n-propylaminomethyl-1,3-butadiene,
2-N, N-di-n-butylaminomethyl-1,3-butadiene,
2-N, N-diallylaminomethyl-1,3-butadiene,
2-N, N-bis (trimethylsilyl) aminomethyl-1,3-butadiene,
2-N, N-bis (tert-butyldimethylsilyl) aminomethyl-1,3-butadiene,
2- (1-aziridinyl) methyl-1,3-butadiene,
2- (1-pyrrolidinyl) methyl-1,3-butadiene,
2- (1-piperidinyl) methyl-1,3-butadiene,
2- (1-hexamethyleneimino) methyl-1,3-butadiene,
1- (2-methylene-3-butenyl) pyrrole,
1- (2-methylene-3-butenyl) imidazole,
1- (2-Methylene-3-butenyl) pyrazole.

Compound in which R ²²² is an ethylene group:
5-N, N-dimethylamino-3-methylene-1-pentene,
5-N, N-diethylamino-3-methylene-1-pentene,
5-N, N-di-n-propylamino-3-methylene-1-pentene,
5-N, N-di-n-butylamino-3-methylene-1-pentene,
5-N, N-diallylamino-3-methylene-1-pentene,
5-N, N-bis (trimethylsilyl) amino-3-methylene-1-pentene,
5-N, N-bis (tert-butyldimethylsilyl) amino-3-methylene-1-pentene,
5- (1-aziridinyl) -3-methylene-1-pentene,
5- (1-pyrrolidinyl) -3-methylene-1-pentene,
5- (1-piperidinyl) -3-methylene-1-pentene,
5- (1-hexamethyleneimino) -3-methylene-1-pentene,
1- (3-methylene-4-pentenyl) pyrrole,
1- (3-methylene-4-pentenyl) imidazole,
1- (3-methylene-4-pentenyl) pyrazole.

As a compound represented by the formula (22), V ²⁰² is a group represented by the formula (22-V1), R ²²¹ in the formula (22-V1) is a phenyl group, and m ² is 1. In addition, examples of the compound in which R ²²² is a phenylene group and A ²⁰² is a substituted amino group include the following compounds.

1- (4-N, N-dimethylaminophenyl) -1-phenylethylene,
1- (4-N, N-diethylaminophenyl) -1-phenylethylene,
1- (4-N, N-dipropylaminophenyl) -1-phenylethylene,
1- (4-N, N-diisopropylaminophenyl) -1-phenylethylene,
1- (4-N, N-dibutylaminophenyl) -1-phenylethylene,
1- (4-N, N-diisobutylaminophenyl) -1-phenylethylene,
1- (4-N, N-di (tert-butyl) aminophenyl) -1-phenylethylene, 1- (4-N, N-diphenylaminophenyl) -1-phenylethylene,
1- (4- (1-aziridinyl) phenyl) -1-phenylethylene,
1- (4- (1-pyrrolidinyl) phenyl) -1-phenylethylene,
1- (4- (1-piperidinyl) phenyl) -1-phenylethylene,
1- (4-hexamethyleneiminophenyl) -1-phenylethylene,
1- (4-morpholinophenyl) -1-phenylethylene,
1- (4- (N, N-bis (trimethylsilyl) amino) phenyl) -1-phenylethylene,
1- (4- (N, N-bis (tert-butyldimethylsilyl) amino) phenyl) -1-phenylethylene,
1- (4- (N, N-bis (triisopropylsilyl) amino) phenyl) -1-phenylethylene,
1- (3-N, N-dimethylaminophenyl) -1-phenylethylene,
1- (3-N, N-diethylaminophenyl) -1-phenylethylene,
1- (3-N, N-dipropylaminophenyl) -1-phenylethylene,
1- (3-N, N-diisopropylaminophenyl) -1-phenylethylene,
1- (3-N, N-dibutylaminophenyl) -1-phenylethylene,
1- (3-N, N-diisobutylaminophenyl) -1-phenylethylene,
1- (3-N, N-di (tert-butyl) aminophenyl) -1-phenylethylene, 1- (3-N, N-diphenylaminophenyl) -1-phenylethylene,
1- (3- (1-aziridinyl) phenyl) -1-phenylethylene,
1- (3- (1-pyrrolidinyl) phenyl) -1-phenylethylene,
1- (3- (1-piperidinyl) phenyl) -1-phenylethylene,
1- (3-hexamethyleneiminophenyl) -1-phenylethylene,
1- (3-morpholinophenyl) -1-phenylethylene,
1- (3- (N, N-bis (trimethylsilyl) amino) phenyl) -1-phenylethylene,
1- (3- (N, N-bis (tert-butyldimethylsilyl) amino) phenyl) -1-phenylethylene,
1- (3- (N, N-bis (triisopropylsilyl) amino) phenyl) -1-phenylethylene.

As a compound represented by the formula (22), V ²⁰² is a group represented by the formula (22-V1), R ²²¹ in the formula (22-V1) is a phenyl group, and m ² is 1. In addition, examples of the compound in which R ²²² is a group represented by the formula (22-Ra) and A ²⁰² is a substituted amino group include the following compounds.

Compound ^{i 2} of the formula (22-Ra) is 1:
1- (4-N, N-dimethylaminomethylphenyl) -1-phenylethylene,
1- (4-N, N-diethylaminomethylphenyl) -1-phenylethylene,
1- (4-N, N-dipropylaminomethylphenyl) -1-phenylethylene,
1- (4-N, N-diisopropylaminomethylphenyl) -1-phenylethylene,
1- (4-N, N-dibutylaminomethylphenyl) -1-phenylethylene,
1- (4-N, N-diisobutylaminomethylphenyl) -1-phenylethylene,
1- (4-N, N-di (tert-butyl) aminomethylphenyl) -1-phenylethylene,
1- (4-N, N-diphenylaminomethylphenyl) -1-phenylethylene,
1- (4- (1-aziridinylmethyl) phenyl) -1-phenylethylene,
1- (4- (1-pyrrolidinylmethyl) phenyl) -1-phenylethylene,
1- (4- (1-piperidinylmethyl) phenyl) -1-phenylethylene,
1- (4-hexamethyleneiminomethylphenyl) -1-phenylethylene,
1- (4-morpholinomethylphenyl) -1-phenylethylene,
1- (4- (N, N-bis (trimethylsilyl) aminomethyl) phenyl) -1-phenylethylene,
1- (4- (N, N-bis (tert-butyldimethylsilyl) amino) methylphenyl) -1-phenylethylene,
1- (4- (N, N-bis (triisopropylsilyl) amino) methylphenyl) -1-phenylethylene.

As a compound represented by the formula (22), V ²⁰² is a group represented by the formula (22-V1), R ²²¹ in the formula (22-V1) is a phenyl group, and m ² is 1. In addition, examples of the compound in which R ²²² is a group represented by the formula (22-Rb) and A ²⁰² is a substituted amino group include the following compounds.

A compound in which j ^{2 of} formula (22-Rb) is 1:
1- (3-N, N-dimethylaminomethylphenyl) -1-phenylethylene,
1- (3-N, N-diethylaminomethylphenyl) -1-phenylethylene,
1- (3-N, N-dipropylaminomethylphenyl) -1-phenylethylene,
1- (3-N, N-diisopropylaminomethylphenyl) -1-phenylethylene,
1- (3-N, N-dibutylaminomethylphenyl) -1-phenylethylene,
1- (3-N, N-diisobutylaminomethylphenyl) -1-phenylethylene,
1- (3-N, N-di (tert-butyl) aminomethylphenyl) -1-phenylethylene,
1- (3-N, N-diphenylaminomethylphenyl) -1-phenylethylene,
1- (3- (1-aziridinylmethyl) phenyl) -1-phenylethylene,
1- (3- (1-pyrrolidinylmethyl) phenyl) -1-phenylethylene,
1- (3- (1-piperidinylmethyl) phenyl) -1-phenylethylene,
1- (3-hexamethyleneiminomethylphenyl) -1-phenylethylene,
1- (3-morpholinomethylphenyl) -1-phenylethylene,
1- (3- (N, N-bis (trimethylsilyl) aminomethyl) phenyl) -1-phenylethylene,
1- (3- (N, N-bis (tert-butyldimethylsilyl) aminomethyl) phenyl) -1-phenylethylene,
1- (3- (N, N-bis (triisopropylsilyl) amino) methylphenyl) -1-phenylethylene.

As a compound represented by the formula (22), V ²⁰² is a group represented by the formula (22-V1), R ²²¹ in the formula (22-V1) is a hydrogen atom, and m ² is 0. In addition, examples of the compound in which A ²⁰² is a nitrogen-containing aliphatic heterocyclic group include the following compounds.

N-methyl-3-vinylpyrrolidine,
N-methyl-4-vinylpiperidine,
N-methyl-3-vinylhexamethyleneimine,
N-methyl-4-vinylhexamethyleneimine.

As a compound represented by the formula (22), V ²⁰² is a group represented by the formula (22-V1), R ²²¹ in the formula (22-V1) is a hydrogen atom, and m ² is 1. In addition, examples of the compound in which R ²²² is a phenylene group and A ²⁰² is a nitrogen-containing aliphatic heterocyclic group include the following compounds.

N-methyl-3- (4-vinylphenyl) pyrrolidine,
N-methyl-4- (4-vinylphenyl) piperidine,
N-methyl-3- (4-vinylphenyl) hexamethyleneimine,
N-methyl-4- (4-vinylphenyl) hexamethyleneimine,
N-methyl-3- (3-vinylphenyl) pyrrolidine,
N-methyl-4- (3-vinylphenyl) piperidine,
N-methyl-3- (3-vinylphenyl) hexamethyleneimine,
N-methyl-4- (3-vinylphenyl) hexamethyleneimine.

As a compound represented by the formula (22), V ²⁰² is a group represented by the formula (22-V1), R ²²¹ in the formula (22-V1) is a hydrogen atom, and m ² is 1. In addition, examples of the compound in which R ²²² is a group represented by the formula (22-Ra) and A ²⁰² is a nitrogen-containing aliphatic heterocyclic group include the following compounds.

Compound ^{i 2} of the formula (22-Ra) is 1:
N-methyl-3- (4-vinylphenylmethyl) pyrrolidine,
N-methyl-4- (4-vinylphenylmethyl) piperidine,
N-methyl-3- (4-vinylphenylmethyl) hexamethyleneimine,
N-methyl-4- (4-vinylphenylmethyl) hexamethyleneimine.

Compound ^{i 2} of the formula (22-Ra) is 2:
N-methyl-3- (4-vinylphenylethyl) pyrrolidine,
N-methyl-4- (4-vinylphenylethyl) piperidine,
N-methyl-3- (4-vinylphenylethyl) hexamethyleneimine,
N-methyl-4- (4-vinylphenylethyl) hexamethyleneimine.

As a compound represented by the formula (22), V ²⁰² is a group represented by the formula (22-V1), R ²²¹ in the formula (22-V1) is a hydrogen atom, and m ² is 1. In addition, examples of the compound in which R ²²² is a group represented by the formula (22-Rb) and A ²⁰² is a nitrogen-containing aliphatic heterocyclic group include the following compounds.

A compound in which j ^{2 of} formula (22-Rb) is 1:
N-methyl-3- (3-vinylphenylmethyl) pyrrolidine,
N-methyl-4- (3-vinylphenylmethyl) piperidine,
N-methyl-3- (3-vinylphenylmethyl) hexamethyleneimine,
N-methyl-4- (3-vinylphenylmethyl) hexamethyleneimine.

Compound ^{j 2} of the formula (22-Rb) is 2:
N-methyl-3- (3-vinylphenylethyl) pyrrolidine,
N-methyl-4- (3-vinylphenylethyl) piperidine,
N-methyl-3- (3-vinylphenylethyl) hexamethyleneimine,
N-methyl-4- (3-vinylphenylethyl) hexamethyleneimine.

As a compound represented by the formula (22), V ²⁰² is a group represented by the formula (22-V1), R ²²¹ in the formula (22-V1) is a methyl group, and m ² is 0. In addition, examples of the compound in which A ²⁰² is a nitrogen-containing aliphatic heterocyclic group include the following compounds.

N-methyl-3-isopropenylpyrrolidine,
N-methyl-4-isopropenylpiperidine,
N-methyl-3-isopropenylhexamethyleneimine,
N-methyl-4-isopropenylhexamethyleneimine.

As a compound represented by the formula (22), V ²⁰² is a group represented by the formula (22-V1), R ²²¹ in the formula (22-V1) is a methyl group, and m ² is 1. In addition, examples of the compound in which R ²²² is a phenylene group and A ²⁰² is a nitrogen-containing aliphatic heterocyclic group include the following compounds.

N-methyl-3- (4-isopropenylphenyl) pyrrolidine,
N-methyl-4- (4-isopropenylphenyl) piperidine,
N-methyl-3- (4-isopropenylphenyl) hexamethyleneimine,
N-methyl-4- (4-isopropenylphenyl) hexamethyleneimine.

As a compound represented by the formula (22), V ²⁰² is a group represented by the formula (22-V1), R ²²¹ in the formula (22-V1) is a methyl group, and m ² is 1. In addition, examples of the compound in which R ²²² is a group represented by the formula (22-Ra) and A ²⁰² is a nitrogen-containing aliphatic heterocyclic group include the following compounds.

Compound ^{i 2} of the formula (22-Ra) is 1:
N-methyl-3- (4-isopropenylphenylmethyl) pyrrolidine,
N-methyl-4- (4-isopropenylphenylmethyl) piperidine,
N-methyl-3- (4-isopropenylphenylmethyl) hexamethyleneimine,
N-methyl-4- (4-isopropenylphenylmethyl) hexamethyleneimine.

Compound ^{i 2} of the formula (22-Ra) is 2:
N-methyl-3- (4-isopropenylphenylethyl) pyrrolidine,
N-methyl-4- (4-isopropenylphenylethyl) piperidine,
N-methyl-3- (4-isopropenylphenylethyl) hexamethyleneimine,
N-methyl-4- (4-isopropenylphenylethyl) hexamethyleneimine.

As a compound represented by the formula (22), V ²⁰² is a group represented by the formula (22-V1), R ²²¹ in the formula (22-V1) is a vinyl group, and m ² is 0. In addition, examples of the compound in which A ²⁰² is a nitrogen-containing aliphatic heterocyclic group include the following compounds.

N-methyl-3- (1-methylene-2-propenyl) pyrrolidine,
N-methyl-4- (1-methylene-2-propenyl) piperidine,
N-methyl-3- (1-methylene-2-propenyl) hexamethyleneimine,
N-methyl-4- (1-methylene-2-propenyl) hexamethyleneimine.

As a compound represented by the formula (22), V ²⁰² is a group represented by the formula (22-V1), R ²²¹ in the formula (22-V1) is a vinyl group, and m ² is 1. In addition, examples of the compound in which R ²²² is an alkylene group and A ²⁰² is a nitrogen-containing aliphatic heterocyclic group include the following compounds.

Compound in which R ²²² is a methylene group:
N-methyl-3- (2-methylene-3-butenyl) pyrrolidine,
N-methyl-4- (2-methylene-3-butenyl) piperidine,
N-methyl-3- (2-methylene-3-butenyl) hexamethyleneimine,
N-methyl-4- (2-methylene-3-butenyl) hexamethyleneimine.

Compound in which R ²²² is an ethylene group:
N-methyl-3- (3-methylene-4-pentenyl) pyrrolidine,
N-methyl-4- (3-methylene-4-pentenyl) piperidine,
N-methyl-3- (3-methylene-4-pentenyl) hexamethyleneimine,
N-methyl-4- (3-methylene-4-pentenyl) hexamethyleneimine.

As a compound represented by the formula (22), V ²⁰² is a group represented by the formula (22-V1), R ²²¹ in the formula (22-V1) is a phenyl group, and m ² is 1. In addition, examples of the compound in which R ²²² is a phenylene group and A ²⁰² is a nitrogen-containing aliphatic heterocyclic group include the following compounds.

1- (4-N-methyl-3-pyrrolidinophenyl) -1-phenylethylene,
1- (4-N-methyl-3-piperidinophenyl) -1-phenylethylene,
1- (4-N-methyl-4-piperidinophenyl) -1-phenylethylene,
1- (4-N-methyl-3-hexamethyleneiminophenyl) -1-phenylethylene,
1- (4-N-methyl-4-hexamethyleneiminophenyl) -1-phenylethylene,
1- (3-N-methyl-3-pyrrolidinophenyl) -1-phenylethylene,
1- (3-N-methyl-3-piperidinophenyl) -1-phenylethylene,
1- (3-N-methyl-4-piperidinophenyl) -1-phenylethylene,
1- (3-N-methyl-3-hexamethyleneiminophenyl) -1-phenylethylene,
1- (3-N-methyl-4-hexamethyleneiminophenyl) -1-phenylethylene.

As a compound represented by the formula (22), V ²⁰² is a group represented by the formula (22-V1), R ²²¹ in the formula (22-V1) is a phenyl group, and m ² is 1. In addition, examples of the compound in which R ²²² is a group represented by the formula (22-Ra) and A ²⁰² is a nitrogen-containing aliphatic heterocyclic group include the following compounds.

Compound ^{i 2} of the formula (22-Ra) is 1:
1- (4-N-methyl-3-pyrrolidinomethylphenyl) -1-phenylethylene,
1- (4-N-methyl-3-piperidinomethylphenyl) -1-phenylethylene,
1- (4-N-methyl-4-piperidinomethylphenyl) -1-phenylethylene,
1- (4-N-methyl-3-hexamethyleneiminomethylphenyl) -1-phenylethylene.

As a compound represented by the formula (22), V ²⁰² is a group represented by the formula (22-V1), R ²²¹ in the formula (22-V1) is a phenyl group, and m ² is 1. In addition, examples of the compound in which R ²²² is a group represented by the formula (22-Rb) and A ²⁰² is a nitrogen-containing aliphatic heterocyclic group include the following compounds.

A compound in which j ^{2 of} formula (22-Rb) is 1:
1- (3-N, N-dimethylaminomethylphenyl) -1-phenylethylene,
1- (3-N, N-diethylaminomethylphenyl) -1-phenylethylene,
1- (3-N, N-dipropylaminomethylphenyl) -1-phenylethylene,
1- (3-N, N-diisopropylaminomethylphenyl) -1-phenylethylene.

As a compound represented by the formula (22), V ²⁰² is a group represented by the formula (22-V1), R ²²¹ in the formula (22-V1) is a hydrogen atom, and m ² is 0. The following compounds can be given as compounds in which A ²⁰² is a nitrogen-containing aromatic heterocyclic group.

N-methyl-2-vinylimidazole,
N-methyl-4-vinylimidazole,
N-methyl-5-vinylimidazole,
2-vinylpyridine,
3-vinylpyridine,
4-vinylpyridine,
2-vinylquinoline,
3-vinyl quinoline,
4-Vinylquinoline.

As a compound represented by the formula (22), V ²⁰² is a group represented by the formula (22-V1), R ²²¹ in the formula (22-V1) is a methyl group, and m ² is 0. The following compounds can be given as compounds in which A ²⁰² is a nitrogen-containing aromatic heterocyclic group.

N-methyl-2-isopropenylimidazole,
N-methyl-4-isopropenylimidazole,
N-methyl-5-isopropenylimidazole,
2-isopropenyl pyridine,
3-isopropenyl pyridine,
4-isopropenyl pyridine,
2-isopropenyl quinoline,
3-isopropenyl quinoline,
4-Isopropenylquinoline.

As a compound represented by the formula (22), V ²⁰² is a group represented by the formula (22-V1), R ²²¹ in the formula (22-V1) is a vinyl group, and m ² is 0. The following compounds can be given as compounds in which A ²⁰² is a nitrogen-containing aromatic heterocyclic group.

N-methyl-2- (1-methylene-2-propenyl) imidazole,
N-methyl-4- (1-methylene-2-propenyl) imidazole,
N-methyl-5- (1-methylene-2-propenyl) imidazole,
2- (1-methylene-2-propenyl) pyridine,
3- (1-methylene-2-propenyl) pyridine,
4- (1-methylene-2-propenyl) pyridine,
2- (1-methylene-2-propenyl) quinoline,
3- (1-methylene-2-propenyl) quinoline,
4- (1-methylene-2-propenyl) quinoline.

As a compound represented by the formula (22), V ²⁰² is a group represented by the formula (22-V1), R ²²¹ in the formula (22-V1) is a vinyl group, and m ² is 1. Yes, examples of the compound in which R ²²² is an alkylene group and A ²⁰² is a nitrogen-containing aromatic heterocyclic group include the following compounds.

Compound in which R ²²² is a methylene group:
N-methyl-2- (2-methylene-3-butenyl) imidazole,
N-methyl-4- (2-methylene-3-butenyl) imidazole,
N-methyl-5- (2-methylene-3-butenyl) imidazole,
2- (2-methylene-3-butenyl) pyridine,
3- (2-methylene-3-butenyl) pyridine,
4- (2-methylene-3-butenyl) pyridine,
2- (2-methylene-3-butenyl) quinoline,
3- (2-methylene-3-butenyl) quinoline,
4- (2-Methylene-3-butenyl) quinoline.

Compound in which R ²²² is an ethylene group:
N-methyl-2- (3-methylene-4-pentenyl) imidazole,
N-methyl-4- (3-methylene-4-pentenyl) imidazole,
N-methyl-5- (3-methylene-4-pentenyl) imidazole,
2- (3-methylene-4-pentenyl) pyridine,
3- (3-methylene-4-pentenyl) pyridine,
4- (3-methylene-4-pentenyl) pyridine,
2- (3-methylene-4-pentenyl) quinoline,
3- (3-methylene-4-pentenyl) quinoline,
4- (3-Methylene-4-pentenyl) quinoline.

The compound represented by formula (22) is preferably a compound in which the group represented by V ²⁰² is represented by formula (22-V1), and R ²²¹ in formula (22-V1) is a hydrogen atom. is there.
More ^preferably at ^{R 221} is a hydrogen atom, ^{m 2} is ^{1, R 222} is a phenylene ^group, Compound ^{A 202} is a substituted amino group represented by the formula ^{(22-A); R 221} is A compound which is a hydrogen atom, m ² is 1, R ²²² is a group represented by formula (22-R), and A ²⁰² is a substituted amino group represented by formula (22-A); R ^In this compound, ²²¹ is a hydrogen atom, m ² is 0, and A ²⁰² is a nitrogen-containing aromatic heterocyclic group.
More preferably, R ²²¹ is a hydrogen atom, m ² is 1, R ²²² is a para-phenylene group or a meta-phenylene group, and A ²⁰² is R ²²⁵ and R ^{226 in} formula (22-A). Is a polymethylene group to which R is bonded; R ²²¹ is a hydrogen atom, m ² is 1, R ²²² is a group represented by the formula (22-Ra) or (22-Rb), and A ²⁰² is A compound in which R ²²⁵ and R ^{226 in} formula (22-A) are a polymethylene group bonded thereto; R ²²¹ is a hydrogen atom, m ² is 0, and A ²⁰² is a pyridyl group.

The compound represented by the formula (22) is particularly preferably
3- (1-pyrrolidinyl) ethylstyrene,
4- (1-pyrrolidinyl) ethylstyrene,
4-vinylpyridine,
2-vinylpyridine.

Examples of the alkoxysilane compound include a tetraalkoxysilane compound, an alkoxysilane compound having an alkyl group, an alkoxysilane compound having a halogen atom, an alkoxysilane compound having an epoxy group, an alkoxysilane compound having a mercapto group, and an alkoxysilane having a substituted amino group. Compound etc. can be mentioned.

Examples of the tetraalkoxysilane compound include tetramethoxysilane, tetraethoxysilane, tetra-n-propoxysilane, tetraisopropoxysilane, tetra-n-butoxysilane, tetraisobutoxysilane, tetra-tert-butoxysilane, tetra- (2 -Ethylhexanoxy) silane and the like.

Examples of the alkoxysilane compound having an alkyl group include methyltrimethoxysilane, methyltriethoxysilane, methyltri-n-propoxysilane, methyltriisopropoxysilane, methyltri-n-butoxysilane, methyltriisobutoxysilane, methyltri-tert- Butoxysilane, methyltri- (2-ethylhexanoxy) silane, dimethyldimethoxysilane, dimethyldiethoxysilane, dimethyldi-n-propoxysilane, dimethyldiisopropoxysilane, dimethyldi-n-butoxysilane, dimethyldiisobutoxysilane, dimethyldi -Tert-butoxysilane, dimethyldi- (2-ethylhexanoxy) silane, etc. can be mentioned.

Examples of the alkoxysilane compound having a halogen atom include trimethoxychlorosilane, triethoxychlorosilane, tri-n-propoxychlorosilane, triisopropoxychlorosilane, tri-n-butoxychlorosilane, triisobutoxychlorosilane, tri-tert-butoxychlorosilane, tri -(2-ethylhexanoxy) chlorosilane, dimethoxydichlorosilane, diethoxydichlorosilane, di-n-propoxydichlorosilane, diisopropoxydichlorosilane, di-n-butoxydichlorosilane, diisobutoxydichlorosilane, di-tert -Butoxydichlorosilane, di- (2-ethylhexanoxy) dichlorosilane, methoxytrichlorosilane, ethoxytrichlorosilane, trimethoxybromosilane, trieth Sibromosilane, tri-n-propoxybromosilane, triisopropoxybromosilane, tri-n-butoxybromosilane, dimethoxydibromosilane, diethoxydibromosilane, di-n-propoxydibromosilane, diisopropoxydibromosilane, di-n -Butoxydibromosilane, methoxytribromosilane, ethoxytribromosilane, trimethoxyiodosilane, triethoxyiodosilane, tri-n-propoxyiodosilane, triisopropoxyiodosilane, tri-n-butoxyiodosilane, dimethoxydiiodo Silane, diethoxydiiodosilane, di-n-propoxydiiodosilane, diisopropoxydiiodosilane, di-n-butoxydiiodosilane, methoxytriiodosilane, ethoxytriiodosila , And the like.

Examples of the alkoxysilane compound having an epoxy group include 2-glycidoxyethyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 4-glycidoxybutyltrimethoxysilane, 2-glycidoxyethyltriethoxysilane, 3-glycidoxypropyltriethoxysilane, 4-glycidoxybutyltriethoxysilane, 2-glycidoxyethyltripropoxysilane, 3-glycidoxypropyltripropoxysilane, 4-glycidoxybutyltripropoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 3-glycidoxypropylethyldimethoxysilane, 3-glycidoxypropylethyldiethoxysilane, 3-glycidoxypropyldimethylmethyl Xysilane, 3-glycidoxypropyldimethylethoxysilane, 3-glycidoxypropyldiethylmethoxysilane, 3-glycidoxypropyldiethylethoxysilane, bis (3-glycidoxypropyl) dimethoxysilane, bis (3-glycid Xylpropyl) diethoxysilane, bis (3-glycidoxypropyl) dipropoxysilane, bis (3-glycidoxypropyl) methylmethoxysilane, bis (3-glycidoxypropyl) methylethoxysilane, bis (3- Glycidoxypropyl) ethylmethoxysilane, bis (3-glycidoxypropyl) ethylethoxysilane, tris (3-glycidoxypropyl) methoxysilane, tris (3-glycidoxypropyl) ethoxysilane, tris (3- Glycidoxypropyl) dipro Xysilane, β- (3,4-epoxycyclohexyl) ethyl-trimethoxysilane, β- (3,4-epoxycyclohexyl) ethyl-triethoxysilane, β- (3,4-epoxycyclohexyl) ethyl-tripropoxysilane, β- (3,4-epoxycyclohexyl) propyl-trimethoxysilane, β- (3,4-epoxycyclohexyl) propyl-triethoxysilane, β- (3,4-epoxycyclohexyl) propyl-tripropoxysilane, β- (3,4-epoxycyclohexyl) ethyl-methyldimethoxysilane, β- (3,4-epoxycyclohexyl) ethyl-methyldiethoxysilane, β- (3,4-epoxycyclohexyl) propyl-methyldimethoxysilane, β- ( 3,4-epoxycyclohexyl) pro Ru-methyldiethoxysilane, β- (3,4-epoxycyclohexyl) ethyl-dimethylmethoxysilane, β- (3,4-epoxycyclohexyl) ethyl-dimethylethoxysilane, β- (3,4-epoxycyclohexyl) propyl -Dimethylmethoxysilane, β- (3,4-epoxycyclohexyl) propyl-dimethylethoxysilane, and the like.

Examples of the alkoxysilane compound having a mercapto group include 2-mercaptoethyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 4-mercaptobutyltrimethoxysilane, 2-mercaptoethyltriethoxysilane, 3-mercaptopropyltriethoxysilane, 4-mercaptobutyltriethoxysilane, 2-mercaptoethyltripropoxysilane, 3-mercaptopropyltripropoxysilane, 4-mercaptobutyltripropoxysilane, 2-mercaptoethylmethyldimethoxysilane, 3-mercaptopropylmethyldimethoxysilane, 4- Mercaptobutylmethyldimethoxysilane, 2-mercaptoethylmethyldiethoxysilane, 3-mercaptopropylmethyldiethoxysilane, 4-mercaptobuty It may be mentioned methyl diethoxy silane, and the like.

（式中、ｐ^２は１〜１０の整数を表し、Ｒ^２３１、Ｒ^２３２及びＲ^２３３は、それぞれ独立にアルキル基又はアルコキシ基を表し、Ｒ^２３１、Ｒ^２３２及びＲ^２３３の少なくとも１つがアルコキシ基であり、Ａ^２０３は置換アミノ基を表す。） Examples of the alkoxysilane compound having a substituted amino group include a compound represented by the following formula (23).

(In the formula, p ² represents an integer of 1 to 10, R ²³¹ , R ²³² and R ²³³ each independently represents an alkyl group or an alkoxy group, and at least one of R ²³¹ , R ²³² and R ²³³ is an alkoxy group. And A ²⁰³ represents a substituted amino group.)

R ²³¹ , R ²³² and R ²³³ each represents an alkyl group or an alkoxy group.

^Examples of the alkyl group of R ²³¹ , R ²³² , and R ²³³ include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, and a tert-butyl group. The alkyl group is preferably an alkyl group having 1 to 10 carbon atoms, more preferably an alkyl group having 1 to 3 carbon atoms, still more preferably a methyl group or an ethyl group.

^Examples of the alkoxy group of R ²³¹ , R ²³² , and R ²³³ include methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, sec-butoxy group, tert-butoxy group, 2-ethylhexano group Kishi can be given. The alkoxy group is preferably an alkoxy group having 1 to 10 carbon atoms, more preferably an alkoxy group having 1 to 3 carbon atoms, and further preferably a methoxy group or an ethoxy group.

At least one of R ²³¹ , R ²³² , and R ²³³ is an alkoxy group, and in order to improve fuel economy, preferably at least two of R ²³¹ , R ²³² , and R ²³³ are alkoxy groups, and more preferably In the ^formula , three of R ²³¹ , R ²³² , and R ²³³ are alkoxy groups.

（式中、Ｒ^２３４及びＲ^２３５は、それぞれ、水素原子、窒素原子及び／又は酸素原子を有していてもよいヒドロカルビル基、あるいは、Ｒ^２３４とＲ^２３５とが結合して、窒素原子及び／又は酸素原子をヘテロ原子として有していてもよいヒドロカルビレン基、又は、Ｒ^２３４とＲ^２３５は１つの基であって、窒素原子に二重結合で結合する基を表す。） In formula (23), A ²⁰³ represents a substituted amino group. The substituted amino group for A ²⁰³ is preferably a group represented by the following formula (23-A).

(Wherein R ²³⁴ and R ²³⁵ are each a hydrogen atom, a nitrogen atom and / or a hydrocarbyl group optionally having an oxygen atom, or R ²³⁴ and R ²³⁵ are bonded to form a nitrogen atom and / Alternatively, a hydrocarbylene group which may have an oxygen atom as a hetero atom, or R ²³⁴ and R ²³⁵ are one group and represent a group bonded to a nitrogen atom with a double bond.)

R ²³⁴ and R ²³⁵ are each a hydrocarbyl group optionally having a hydrogen atom, a nitrogen atom and / or an oxygen atom, or R ²³⁴ and R ²³⁵ are bonded to form a nitrogen atom and / or an oxygen atom. The hydrocarbylene group which may have, or ^R234 and ^R235 are one group, Comprising: The group couple | bonded with a nitrogen atom with a double bond is represented.

^Examples of the hydrocarbyl group of R ²³⁴ and R ²³⁵ include alkyl groups such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, and tert-butyl group; vinyl group, allyl group, Examples thereof include alkenyl groups such as 1-propenyl group and 1-methylethenyl group; alkynyl groups such as ethynyl group and propargyl group; aryl groups such as phenyl group, tolyl group and xylyl group; and aralkyl groups such as benzyl group.

Examples of the hydrocarbyl group having a nitrogen atom of R ²³⁴ and R ²³⁵ include dialkylaminoalkyl groups such as a dimethylaminomethyl group, a dimethylaminoethyl group, a dimethylaminopropyl group, a diethylaminomethyl group, a diethylaminoethyl group, and a diethylaminopropyl group. Can do.

Examples of the hydrocarbyl group having an oxygen atom of R ²³⁴ and R ²³⁵ include an alkoxyalkyl group such as a methoxymethyl group, a methoxyethyl group, a methoxypropyl group, an ethoxymethyl group, an ethoxyethyl group, and an ethoxypropyl group; a 2-oxiranyl group, 2 A monooxacycloalkyl group such as an oxetanyl group or 2-tetrahydrofuranyl group; a dioxacycloalkyl group such as a 2-dioxolanyl group; an alkyl group substituted with a monooxacycloalkyl group such as a glycidyl group or a tetrahydrofurfuryl group; A 3,4-epoxycyclohexyl group can be mentioned.

In this specification, the monooxacycloalkyl group represents a group in which one CH ₂ of the cycloalkyl group is replaced with an oxygen atom. The dioxacycloalkyl group represents a group in which _two CH ₂ of the cycloalkyl group are replaced with an oxygen atom.

The number of carbon atoms of the hydrocarbyl group which may have a nitrogen atom and / or an oxygen atom of R ²³⁴ and R ²³⁵ is preferably 1 to 10, and more preferably 1 to 6.

^Examples of the group to which R ²³⁴ and R ²³⁵ are bonded include a hydrocarbylene group, a hydrocarbylene group having a nitrogen atom, and a hydrocarbylene group having an oxygen atom. Examples of the hydrocarbylene group include alkylene groups such as trimethylene group, tetramethylene group, pentamethylene group, and hexamethylene group. As the hydrocarbylene group having a nitrogen atom, a group represented by —CH ₂ CH ₂ —NH—CH ₂ —, a group represented by —CH ₂ CH ₂ —N═CH—, —CH═CH—N A group represented by ═CH— and a group represented by —CH ₂ CH ₂ —NH—CH ₂ CH ₂ — can be exemplified. Examples of the hydrocarbylene group having an oxygen atom include a group represented by —CH ₂ CH ₂ —O—CH ₂ CH ₂ —.

The number of carbon atoms of the group to which R ²³⁴ and R ²³⁵ are bonded is preferably 2 to 20, and more preferably 2 to 12.

One group in which R ²³⁴ and R ²³⁵ are bonded to the nitrogen atom with a double bond is ethylidene group, propylidene group, butylidene group, 1-methylethylidene group, 1-methylpropylidene group, 1,3-dimethylbutylidene. A hydrocarbylidene group such as a group; 4-N, N-dimethylaminobenzylidene group and the like.

The number of carbon atoms of one group in which R ²³⁴ and R ²³⁵ are bonded to the nitrogen atom with a double bond is preferably 2 to 20, and more preferably 2 to 12.

R ²³⁴ and R ²³⁵ are preferably a hydrocarbyl group, a hydrocarbylene group in which R ²³⁴ and R ²³⁵ are bonded, or R ²³⁴ and R ²³⁵ are one group, and a nitrogen atom Is a hydrocarbylidene group which is a group bonded by a double bond, more preferably a hydrocarbyl group, and still more preferably an alkyl group. The alkyl group is preferably a methyl group or an ethyl group.

p ² is an integer of 1 to 10, preferably 2 to 4, more preferably 3.

As a compound represented by Formula (23), as a compound in which R ²³⁴ and R ²³⁵ are alkyl groups,
[3- (dimethylamino) propyl] trimethoxysilane,
[3- (diethylamino) propyl] trimethoxysilane,
[3- (ethylmethylamino) propyl] trimethoxysilane,
[3- (dimethylamino) propyl] triethoxysilane,
[3- (diethylamino) propyl] triethoxysilane,
[3- (dialkylamino) propyl] trialkoxysilanes such as [3- (ethylmethylamino) propyl] triethoxysilane;

[3- (dimethylamino) propyl] methyldimethoxysilane,
[3- (diethylamino) propyl] methyldimethoxysilane,
[3- (ethylmethylamino) propyl] methyldimethoxysilane,
[3- (dimethylamino) propyl] ethyldimethoxysilane,
[3- (diethylamino) propyl] ethyldimethoxysilane,
[3- (ethylmethylamino) propyl] ethyldimethoxysilane,
[3- (dimethylamino) propyl] methyldiethoxysilane,
[3- (diethylamino) propyl] methyldiethoxysilane,
[3- (ethylmethylamino) propyl] methyldiethoxysilane,
[3- (dimethylamino) propyl] ethyldiethoxysilane,
[3- (diethylamino) propyl] ethyldiethoxysilane,
[3- (dialkylamino) propyl] alkyl dialkoxysilanes such as [3- (ethylmethylamino) propyl] ethyldiethoxysilane;

[3- (dimethylamino) propyl] dimethylmethoxysilane,
[3- (diethylamino) propyl] dimethylmethoxysilane,
[3- (dimethylamino) propyl] diethylmethoxysilane,
[3- (diethylamino) propyl] diethylmethoxysilane,
[3- (dimethylamino) propyl] dimethylethoxysilane,
[3- (diethylamino) propyl] dimethylethoxysilane,
[3- (dimethylamino) propyl] diethylethoxysilane,
[3- (Dialkylamino) propyl] dialkylalkoxysilanes such as [3- (diethylamino) propyl] diethylethoxysilane can be mentioned.

As a compound represented by Formula (23), as a compound in which R ²³⁴ and R ²³⁵ are alkoxyalkyl groups,
{3- [bis (methoxymethyl) amino] propyl} trimethoxysilane,
{3- [bis (ethoxymethyl) amino] propyl} trimethoxysilane,
{3- [bis (methoxyethyl) amino] propyl} trimethoxysilane,
{3- [bis (ethoxyethyl) amino] propyl} trimethoxysilane,
{3- [bis (methoxymethyl) amino] propyl} triethoxysilane,
{3- [bis (ethoxymethyl) amino] propyl} triethoxysilane,
{3- [bis (methoxyethyl) amino] propyl} triethoxysilane,
{3- [bis (alkoxyalkyl) amino] propyl} trialkoxysilanes such as {3- [bis (ethoxyethyl) amino] propyl} triethoxysilane;

{3- [bis (methoxymethyl) amino] propyl} methyldimethoxysilane,
{3- [bis (ethoxymethyl) amino] propyl} methyldimethoxysilane,
{3- [bis (methoxyethyl) amino] propyl} methyldimethoxysilane,
{3- [bis (ethoxyethyl) amino] propyl} methyldimethoxysilane,
{3- [bis (methoxymethyl) amino] propyl} ethyldimethoxysilane,
{3- [bis (ethoxymethyl) amino] propyl} ethyldimethoxysilane,
{3- [bis (methoxyethyl) amino] propyl} ethyldimethoxysilane,
{3- [bis (ethoxyethyl) amino] propyl} ethyldimethoxysilane,
{3- [bis (methoxymethyl) amino] propyl} methyldiethoxysilane,
{3- [bis (ethoxymethyl) amino] propyl} methyldiethoxysilane,
{3- [bis (methoxyethyl) amino] propyl} methyldiethoxysilane,
{3- [bis (ethoxyethyl) amino] propyl} methyldiethoxysilane,
{3- [bis (methoxymethyl) amino] propyl} ethyldiethoxysilane,
{3- [bis (ethoxymethyl) amino] propyl} ethyldiethoxysilane,
{3- [bis (methoxyethyl) amino] propyl} ethyldiethoxysilane,
{3- [bis (alkoxyalkyl) amino] propyl} alkyl dialkoxysilanes such as {3- [bis (ethoxyethyl) amino] propyl} ethyldiethoxysilane;

{3- [bis (methoxymethyl) amino] propyl} dimethylmethoxysilane,
{3- [bis (ethoxymethyl) amino] propyl} dimethylmethoxysilane,
{3- [bis (methoxyethyl) amino] propyl} dimethylmethoxysilane,
{3- [bis (ethoxyethyl) amino] propyl} dimethylmethoxysilane,
{3- [bis (methoxymethyl) amino] propyl} diethylmethoxysilane,
{3- [bis (ethoxymethyl) amino] propyl} diethylmethoxysilane,
{3- [bis (methoxyethyl) amino] propyl} diethylmethoxysilane,
{3- [bis (ethoxyethyl) amino] propyl} diethylmethoxysilane,
{3- [bis (methoxymethyl) amino] propyl} dimethylethoxysilane,
{3- [bis (ethoxymethyl) amino] propyl} dimethylethoxysilane,
{3- [bis (methoxyethyl) amino] propyl} dimethylethoxysilane,
{3- [bis (ethoxyethyl) amino] propyl} dimethylethoxysilane,
{3- [bis (methoxymethyl) amino] propyl} diethylethoxysilane,
{3- [bis (ethoxymethyl) amino] propyl} diethylethoxysilane,
{3- [bis (methoxyethyl) amino] propyl} diethylethoxysilane,
Mention may be made of {3- [bis (alkoxyalkyl) amino] propyl} dialkylalkoxysilanes such as {3- [bis (ethoxyethyl) amino] propyl} diethylethoxysilane.

As a compound represented by Formula (23), as a compound in which R ²³⁴ and R ²³⁵ are oxiranyl groups,
{3- [di (oxiranyl) amino] propyl} trimethoxysilane,
{3- [di (oxiranyl) amino] propyl} triethoxysilane,
{3- [di (oxiranyl) amino] propyl} methyldimethoxysilane,
{3- [di (oxiranyl) amino] propyl} ethyldimethoxysilane,
{3- [di (oxiranyl) amino] propyl} methyldiethoxysilane,
{3- [di (oxiranyl) amino] propyl} ethyldiethoxysilane,
{3- [di (oxiranyl) amino] propyl} dimethylmethoxysilane,
{3- [di (oxiranyl) amino] propyl} diethylmethoxysilane,
{3- [di (oxiranyl) amino] propyl} dimethylethoxysilane,
Examples include {3- [di (oxiranyl) amino] propyl} diethylethoxysilane.

As the compound represented by the formula (23), as a compound in which R ²³⁴ and R ²³⁵ are tetrahydrofuranyl groups,
{3- [di (tetrahydrofuranyl) amino] propyl} trimethoxysilane,
{3- [di (tetrahydrofuranyl) amino] propyl} triethoxysilane,
{3- [di (tetrahydrofuranyl) amino] propyl} methyldimethoxysilane,
{3- [di (tetrahydrofuranyl) amino] propyl} ethyldimethoxysilane,
{3- [di (tetrahydrofuranyl) amino] propyl} methyldiethoxysilane,
{3- [di (tetrahydrofuranyl) amino] propyl} ethyldiethoxysilane,
{3- [di (tetrahydrofuranyl) amino] propyl} dimethylmethoxysilane,
{3- [di (tetrahydrofuranyl) amino] propyl} diethylmethoxysilane,
{3- [di (tetrahydrofuranyl) amino] propyl} dimethylethoxysilane,
Examples include {3- [di (tetrahydrofuranyl) amino] propyl} diethylethoxysilane.

As a compound represented by Formula (23), as a compound in which R ²³⁴ and R ²³⁵ are glycidyl groups,
{3- [di (glycidyl) amino] propyl} trimethoxysilane,
{3- [di (glycidyl) amino] propyl} triethoxysilane,
{3- [di (glycidyl) amino] propyl} methyldimethoxysilane,
{3- [di (glycidyl) amino] propyl} ethyldimethoxysilane,
{3- [di (glycidyl) amino] propyl} methyldiethoxysilane,
{3- [di (glycidyl) amino] propyl} ethyldiethoxysilane,
{3- [di (glycidyl) amino] propyl} dimethylmethoxysilane,
{3- [di (glycidyl) amino] propyl} diethylmethoxysilane,
{3- [di (glycidyl) amino] propyl} dimethylethoxysilane,
Examples include {3- [di (glycidyl) amino] propyl} diethylethoxysilane.

As the compound represented by the formula (23), as a compound in which R ²³⁴ and R ²³⁵ are tetrahydrofurfuryl groups,
{3- [di (tetrahydrofurfuryl) amino] propyl} trimethoxysilane,
{3- [di (tetrahydrofurfuryl) amino] propyl} triethoxysilane,
{3- [di (tetrahydrofurfuryl) amino] propyl} methyldimethoxysilane,
{3- [di (tetrahydrofurfuryl) amino] propyl} ethyldimethoxysilane,
{3- [di (tetrahydrofurfuryl) amino] propyl} methyldiethoxysilane,
{3- [di (tetrahydrofurfuryl) amino] propyl} ethyldiethoxysilane,
{3- [di (tetrahydrofurfuryl) amino] propyl} dimethylmethoxysilane,
{3- [di (tetrahydrofurfuryl) amino] propyl} diethylmethoxysilane,
{3- [di (tetrahydrofurfuryl) amino] propyl} dimethylethoxysilane,
Examples include {3- [di (tetrahydrofurfuryl) amino] propyl} diethylethoxysilane.

As the compound represented by the formula (23), as a compound in which R ²³⁴ and R ²³⁵ are bonded,
3- (1-piperidinyl) propyltrimethoxysilane,
3- (1-piperidinyl) propyltriethoxysilane,
3- (1-piperidinyl) propylmethyldimethoxysilane,
3- (1-piperidinyl) propylethyldimethoxysilane,
3- (1-piperidinyl) propylmethyldiethoxysilane,
3- (1-piperidinyl) propylethyldiethoxysilane,
3- (1-hexamethyleneimino) propyltrimethoxysilane,
3- (1-hexamethyleneimino) propyltriethoxysilane,
3- (1-hexamethyleneimino) propylmethyldimethoxysilane,
3- (1-hexamethyleneimino) propylethyldimethoxysilane,
3- (1-hexamethyleneimino) propylmethyldiethoxysilane,
3- (1-hexamethyleneimino) propylethyldiethoxysilane,
3-morpholinopropyltrimethoxysilane,
3-morpholinopropyltriethoxysilane,
3-morpholinopropylmethyldimethoxysilane,
3-morpholinopropylethyldimethoxysilane,
3-morpholinopropylmethyldiethoxysilane,
There may be mentioned 3-morpholinopropylethyldiethoxysilane.

As the compound represented by the formula (23), as a compound in which R ²³⁴ and R ²³⁵ are one group bonded to a nitrogen atom by a double bond,
N- (1,3-dimethylbutylidene) -3- (trimethoxysilyl) -1-propanamine,
N- (1,3-dimethylbutylidene) -3- (triethoxysilyl) -1-propanamine can be mentioned.

As the compound represented by the formula (23),
Preferably,
[3- (dialkylamino) propyl] trialkoxysilane,
More preferably,
[3- (dimethylamino) propyl] trimethoxysilane,
[3- (diethylamino) propyl] trimethoxysilane,
[3- (dimethylamino) propyl] triethoxysilane,
[3- (diethylamino) propyl] triethoxysilane,
More preferably,
[3- (Diethylamino) propyl] trimethoxysilane.

The content of the monomer unit based on the compound represented by the formula (21) is preferably 0.01% by mass or more per 100% by mass of the conjugated diene polymer in order to improve fuel efficiency. Preferably it is 0.02 mass% or more, More preferably, it is 0.05 mass% or more. In order to improve economic efficiency and wear resistance, the content is preferably 20% by mass or less, more preferably 2% by mass or less, and still more preferably 1% by mass or less.

In the monomer unit based on the compound represented by the formula (21), the groups represented by X ²⁰¹ , X ²⁰² and X ²⁰³ may be a hydroxyl group by hydrolysis or the like.

The content of the monomer unit based on the compound represented by the formula (22) is preferably 0.01% by mass or more per 100% by mass of the conjugated diene polymer in order to improve fuel efficiency and wear resistance. More preferably, it is 0.02 mass% or more, More preferably, it is 0.05 mass% or more. In order to improve economic efficiency and wear resistance, the content is preferably 20% by mass or less, more preferably 2% by mass or less, and still more preferably 1% by mass or less.

The conjugated diene polymer (B) may have a structural unit (vinyl aromatic hydrocarbon unit) based on a vinyl aromatic hydrocarbon in order to improve wear resistance. Examples of the vinyl aromatic hydrocarbon include styrene, α-methylstyrene, vinyl toluene, vinyl naphthalene, divinyl benzene, trivinyl benzene, and divinyl naphthalene. Styrene is preferable.

The content of the vinyl aromatic hydrocarbon unit is 0% by mass or more (the content of the conjugated diene unit is 100% by mass or less), where the total amount of the conjugated diene unit and the vinyl aromatic hydrocarbon unit is 100% by mass. The content is preferably 10% by mass or more (the content of the conjugated diene unit is 90% by mass or less), and more preferably 15% by mass or more (the content of the conjugated diene unit is 85% by mass or less). In order to improve fuel economy, the content of vinyl aromatic hydrocarbon units is preferably 50% by mass or less (the content of conjugated diene units is 50% by mass or more), more preferably 45% by mass or less. (The content of the conjugated diene unit is 55% by mass or more).

The Mooney viscosity (ML _{1 + 4} ) of the conjugated diene polymer (B) is preferably 10 or more, more preferably 20 or more, in order to increase the wear resistance. Moreover, in order to improve workability, Preferably it is 200 or less, More preferably, it is 150 or less. The Mooney viscosity (ML _{1 + 4} ) is measured at 100 ° C. according to JIS K6300 (1994).

The vinyl bond content of the conjugated diene polymer (B) is preferably 70 mol% or less, more preferably 60 mol% or less, in order to improve fuel efficiency, with the content of the conjugated diene unit being 100 mol%. It is. Moreover, in order to improve wet grip property, Preferably it is 20 mol% or more, More preferably, it is 40 mol% or more, More preferably, it is 50 mol% or more. The vinyl bond amount is determined from the absorption intensity in the vicinity of 910 cm ^−1, which is the absorption peak of the vinyl group, by infrared spectroscopy.

The molecular weight distribution of the conjugated diene polymer (B) is preferably 1 to 5 and more preferably 1 to 2 in order to improve fuel economy. The molecular weight distribution is obtained by measuring the number average molecular weight (Mn) and the weight average molecular weight (Mw) by gel permeation chromatography (GPC) method and dividing Mw by Mn.

Suitable method for producing a conjugated diene polymer (B), it is possible to increase the manufacturing method having the following steps A ² and Step B ^2.
(Step A ² ): In a hydrocarbon solvent, a monomer component containing a conjugated diene, a compound represented by the above formula (21) and a compound represented by the above formula (22) is polymerized with an alkali metal catalyst. A polymer unit having a monomer unit based on a conjugated diene, a monomer unit based on a compound represented by the formula (21), and a monomer unit based on a compound represented by the formula (22). A step of obtaining a polymer having an alkali metal derived from an alkali metal catalyst at least at one end.
(Step B ² ): A step of reacting the polymer obtained in Step A ² with an alkoxysilane compound.

The alkali metal catalyst used in step A ^2, may be mentioned alkali metal, organic alkali metal compound, a complex of an alkali metal and a polar compound, such as an oligomer having an alkali metal. Examples of the alkali metal include lithium, sodium, potassium, rubidium, cesium and the like. Examples of the organic alkali metal compound include ethyl lithium, n-propyl lithium, iso-propyl lithium, n-butyl lithium, sec-butyl lithium, t-octyl lithium, n-decyl lithium, phenyl lithium, 2-naphthyl lithium, 2 -Butylphenyllithium, 4-phenylbutyllithium, cyclohexyllithium, 4-cyclopentyllithium, dimethylaminopropyllithium, diethylaminopropyllithium, t-butyldimethylsiloxypropyllithium, N-morpholinopropyllithium, lithium hexamethyleneimide, lithium pyrrole Zido, lithium piperidide, lithium heptamethylene imide, lithium dodecamethylene imide, 1,4-dilithio-2-butene, sodium naphthalenide, sodium Bifenirido, such as potassium napthalenide can be mentioned. Examples of the complex of the alkali metal and the polar compound include potassium-tetrahydrofuran complex and potassium-diethoxyethane complex, and the oligomer having the alkali metal includes sodium salt of α-methylstyrene tetramer. I can give you. An organic lithium compound or an organic sodium compound is preferable, and an organic lithium compound having 2 to 20 carbon atoms or an organic sodium compound having 2 to 20 carbon atoms is more preferable.

Hydrocarbon solvents used in step A ² is a solvent that does not deactivate the organic alkali metal compound catalyst may be mentioned aliphatic hydrocarbons, aromatic hydrocarbons, and alicyclic hydrocarbons.
Examples of the aliphatic hydrocarbon include propane, n-butane, iso-butane, n-pentane, iso-pentane, n-hexane, propene, 1-butene, iso-butene, trans-2-butene, cis-2- Examples include butene, 1-pentene, 2-pentene, 1-hexene, 2-hexene and the like. Examples of the aromatic hydrocarbon include benzene, toluene, xylene, and ethylbenzene. Examples of the alicyclic hydrocarbon include cyclopentane and cyclohexane. One or more of these may be used, and the hydrocarbon solvent may be a mixture of various components such as industrial hexane. Preferably, it is a hydrocarbon having 2 to 12 carbon atoms.

In step A ^2, a hydrocarbon solvent, the alkali metal catalyst, a conjugated diene, by polymerizing a monomer component including the above formulas (21) and the compound represented by the compound represented by the above formula (22), A polymer having a monomer unit based on a conjugated diene, a monomer unit based on a compound represented by the above formula (21), and a monomer unit based on a compound represented by the above formula (22) is produced. Examples of the conjugated diene include 1,3-butadiene, isoprene, 1,3-pentadiene, 2,3-dimethyl-1,3-butadiene, and 1,3-hexadiene. One or more of these are used. 1,3-butadiene and isoprene are preferred.

The amount of the compound represented by the formula (21) is preferably 0.01% by mass or more in order to improve the fuel efficiency by setting the total amount of the monomer components used in the polymerization to 100% by mass. More preferably, it is 0.02 mass% or more, More preferably, it is 0.05 mass% or more. In order to improve economic efficiency and wear resistance, it is preferably 20% by mass or less, more preferably 2% by mass or less, still more preferably 1% by mass or less, and particularly preferably 0.5% by mass or less. is there.

The amount of the compound represented by the formula (22) is preferably 0.01% by mass in order to increase the fuel efficiency and wear resistance, with the total amount of the monomer components used in the polymerization being 100% by mass. % Or more, more preferably 0.02 mass% or more, still more preferably 0.05 mass% or more. In order to improve economic efficiency and wear resistance, it is preferably 20% by mass or less, more preferably 2% by mass or less, still more preferably 1% by mass or less, and particularly preferably 0.5% by mass or less. is there.

In the polymerization reaction, the total amount of the conjugated diene, the compound represented by the formula (21), the compound represented by the formula (22) and the vinyl aromatic hydrocarbon is determined by the amount of the monomer component used in the polymerization. In order to increase the wear resistance when the total use amount is 100% by mass, it is preferably 99.9% by mass or more, more preferably 99.95% by mass or more, and further preferably 100% by mass.

In step A ^2, conjugated diene, the compound represented by the formula (21) and the compound represented by the formula in (22) may be carried out polymerization by combining vinyl aromatic hydrocarbon, vinyl aromatic hydrocarbons Examples thereof include styrene, α-methylstyrene, vinyl toluene, vinyl naphthalene, divinyl benzene, trivinyl benzene, divinyl naphthalene and the like. Styrene is preferable.

The amount of vinyl aromatic hydrocarbon used is preferably 10% by mass or more (the amount of conjugated diene used) in order to increase the strength with the total amount of conjugated diene and vinyl aromatic hydrocarbon being 100% by mass. Is 90% by mass or less), more preferably 15% by mass or more (the amount of conjugated diene used is 85% by mass or less). In order to improve fuel efficiency, the amount of vinyl aromatic hydrocarbon used is preferably 50% by mass or less (the amount of conjugated diene used is 50% by mass or more), more preferably 45% by mass or less (conjugated). The amount of diene used is 55% by mass or more).

In the polymerization reaction, the total amount of the conjugated diene, the compound represented by the formula (21), the compound represented by the formula (22) and the vinyl aromatic hydrocarbon is 100. In order to increase the strength, it is preferably 99.9% by mass or more, more preferably 99.95% by mass or more, and still more preferably 100% by mass.

Polymerization reaction is an agent that adjusts the amount of vinyl bonds of conjugated diene units, an agent that adjusts the distribution of monomer units based on monomers other than conjugated diene units and conjugated dienes in the conjugated diene polymer chain , And collectively referred to as “regulators”). Examples of such agents include ether compounds, tertiary amines, and phosphine compounds. Examples of the ether compound include cyclic ethers such as tetrahydrofuran, tetrahydropyran, and 1,4-dioxane; aliphatic monoethers such as diethyl ether and dibutyl ether; ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, and diethylene glycol diethyl ether. And aliphatic diethers such as diethylene glycol dibutyl ether; aromatic ethers such as diphenyl ether and anisole. Examples of the tertiary amine include triethylamine, tripropylamine, tributylamine, N, N, N ′, N′-tetramethylethylenediamine, N, N-diethylaniline, pyridine, quinoline and the like. Examples of the phosphine compound include trimethylphosphine, triethylphosphine, triphenylphosphine, and the like. One or more of these are used.

The polymerization temperature in step ^{A 2} is usually 25 to 100 ° C., preferably from 35 to 90 ° C..
More preferably, it is 50-80 degreeC. The polymerization time is usually 10 minutes to 5 hours.

Step A ² may be a multi-stage process. For example, it may be a step having the following steps a1-2, a2-2, and a3-2.
(Step a1-2): A conjugated diene, a compound represented by the formula (21) and a vinyl aromatic hydrocarbon are polymerized with an alkali metal catalyst in a hydrocarbon solvent, and the alkali metal derived from the catalyst is polymerized into a polymer chain. Step of obtaining a conjugated diene polymer at the terminal (step a2-2): The compound represented by formula (22) is added to the hydrocarbon solution obtained in step a1-2, and the formula (22) Is reacted with the polymer chain end of the conjugated diene polymer obtained in the step a1, and the alkali metal derived from the alkali metal catalyst is added to the monomer unit based on the compound represented by the formula (22). Step of obtaining a conjugated diene polymer having a bonded structure at the end of the polymer chain (step a3-2): adding conjugated diene and vinyl aromatic hydrocarbon to the hydrocarbon solution obtained in step a2-2 , Conjugated dienes and vinyl aromatics Step of polymerizing a hydride polymer chain end of the obtained conjugated diene polymer in the step a2

In Step B ^2, the amount of the alkoxysilane compound to be reacted with the polymer prepared in step A ² is an alkali metal per mole derived from the organic alkali metal catalyst, usually from 0.1 to 3 mol, preferably, It is 0.5-2 mol, More preferably, it is 0.7-1.5 mol.

（式中、Ｖ^３０１は重合性炭素−炭素二重結合を有するヒドロカルビル基を表し、Ｓ^３０１は置換シリル基を表す。）

（式中、Ｖ^３０２は重合性炭素−炭素二重結合を有するヒドロカルビル基を表し、Ａ^３０２は置換アミノ基、又は、含窒素複素環基を表す。）
化合物（Ｇ）：置換基を有していてもよいアミノ基及びカルボニル基を有する化合物、並びに置換基を有していてもよいアミノ基及びチオカルボニル基を有する化合物からなる化合物群から選ばれる少なくとも１種の化合物。 The conjugated diene polymer (C) according to the third aspect of the present invention includes a monomer unit based on a conjugated diene, a monomer unit based on a compound represented by the following formula (31), and the following formula (32). And at least one end of the copolymer is modified with the following compound (G).

(In the formula, V ³⁰¹ represents a hydrocarbyl group having a polymerizable carbon-carbon double bond, and S ³⁰¹ represents a substituted silyl group.)

(In the formula, V ³⁰² represents a hydrocarbyl group having a polymerizable carbon-carbon double bond, and A ³⁰² represents a substituted amino group or a nitrogen-containing heterocyclic group.)
Compound (G): at least selected from the group consisting of a compound having an amino group and a carbonyl group which may have a substituent, and a compound having an amino group and a thiocarbonyl group which may have a substituent One compound.

As used herein, a hydrocarbyl group represents a hydrocarbon residue. The hydrocarbylene group represents a divalent hydrocarbon residue. A nitrogen-containing heterocyclic group represents a group obtained by removing one hydrogen atom from a carbon atom of a heterocyclic ring of a compound having a nitrogen-containing heterocyclic ring, and the nitrogen-containing heterocyclic ring is an aromatic having a nitrogen atom as a hetero atom constituting the ring. Represents a family heterocycle.

Examples of the conjugated diene include 1,3-butadiene, isoprene, 1,3-pentadiene, 2,3-dimethyl-1,3-butadiene, 1,3-hexadiene and the like, and one or more of these are used. . The conjugated diene is preferably 1,3-butadiene or isoprene.

V ³⁰¹ in the formula (31) represents a hydrocarbyl group having a polymerizable carbon-carbon double bond.

V ³⁰¹ is preferably a group represented by the following formula (31-V).

（式中、ｎ^３は０又は１であり、Ｒ^３１１、Ｒ^３１３及びＲ^３１４は、それぞれ独立に水素原子又はヒドロカルビル基を表し、Ｒ^３１２はヒドロカルビレン基を表す。）

(In the formula, n ³ is 0 or 1, R ³¹¹ , R ³¹³ and R ³¹⁴ each independently represent a hydrogen atom or a hydrocarbyl group, and R ³¹² represents a hydrocarbylene group.)

In the formula (31-V), n ³ represents 0 or 1.

^Examples of the hydrocarbyl group of R ³¹¹ , R ³¹³ and R ³¹⁴ include an alkyl group, an alkenyl group, and an aryl group. Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, and a tert-butyl group, and a methyl group is preferable. Examples of the alkenyl group include a vinyl group, an allyl group, a 1-propenyl group, and a 1-methylethenyl group, and a vinyl group is preferable. Examples of the aryl group include a phenyl group, a methylphenyl group, and an ethylphenyl group, and a phenyl group is preferable.

R ³¹¹ , R ³¹³ and R ³¹⁴ are preferably a hydrogen atom, a methyl group, a vinyl group or a phenyl group, and more preferably a hydrogen atom.

^Examples of the hydrocarbylene group for R ³¹² include an alkylene group, an arylene group, and a group in which an arylene group and an alkylene group are bonded.

Examples of the alkylene group include a methylene group, an ethylene group, and a trimethylene group. Preferably, it is a methylene group or an ethylene group. Examples of the arylene group include a phenylene group, a naphthylene group, and a biphenylene group. A phenylene group is preferred.

Examples of the group in which an arylene group and an alkylene group are bonded include a group in which a phenylene group and an alkylene group are bonded, a group in which a naphthylene group and an alkylene group are bonded, and a group in which a biphenylene group and an alkylene group are bonded. .
In addition, as the group in which the arylene group and the alkylene group are bonded, it is preferable that the carbon atom of the arylene group of the group is bonded to the carbon atom to which R ³¹¹ of the formula (31-V) is bonded.

In a group in which a phenylene group and an alkylene group are bonded (phenylene-alkylene group (for example, a group represented by the following formula (31-R))), the position of a carbon atom on the benzene ring from which a hydrogen atom is removed Depending on the position of the carbon atom on the benzene ring to which the alkylene group is bonded, a para-phenylene-alkylene group (for example, a group represented by the following formula (31-Ra)), a meta-phenylene-alkylene group (for example, A group represented by the following formula (31-Rb)), and an ortho-phenylene-alkylene group (for example, a group represented by the following formula (31-Rc)).

（式中、ｄ^３は１〜１０の整数を表し、（ＣＨ_２）_ｄ３はベンゼン環上の置換基である。）

(Wherein, ^{d 3} represents an integer of 1 to _{10, (CH 2) d3} is a substituent on the benzene ring.)

（式中、ｅ^３、ｆ^３、ｇ^３は、それぞれ、１〜１０の整数を表す。）

^{(Wherein, e 3, f 3, g} 3 , respectively integer of 1 to 10.)

The group in which an arylene group and an alkylene group are bonded is preferably a group in which a phenylene group and an alkylene group are bonded, and more preferably a group represented by the above formula (31-Ra) or the above formula (31 -Rb), more preferably a para-phenylene-methylene group (a group represented by the formula (31-Ra) where e ³ = 1), a meta-phenylene-methylene group (f ³ = 1 group represented by the formula (31-Rb)), para-phenylene-ethylene group (group represented by the formula (31-Ra) where e ³ = 2), meta-phenylene-ethylene group ( f ³ = 2 and a group represented by the formula (31-Rb)).

Examples of the group represented by the formula (31-V) include the following groups.

As the group in which R ³¹¹ , R ³¹³ and R ³¹⁴ are hydrogen atoms, a vinyl group, a vinylmethyl group, a vinylethyl group, a 4-vinylphenyl group, a 3-vinylphenyl group, a (4-vinylphenyl) methyl group, 2- ( 4-vinylphenyl) ethyl group, (3-vinylphenyl) methyl group, 2- (3-vinylphenyl) ethyl group and the like can be mentioned.

^Examples of the group in which R ³¹¹ is a methyl group and R ³¹³ and R ³¹⁴ are hydrogen atoms include an isopropenyl group, a methallyl group, a 4-isopropenylphenyl group, a 3-isopropenylphenyl group, and (4-isopropenylphenyl) methyl. Group, 2- (4-isopropenylphenyl) ethyl group, (3-isopropenylphenyl) methyl group, 2- (3-isopropenylphenyl) ethyl group and the like.

^Examples of the group in which R ³¹¹ is a vinyl group and R ³¹³ and R ^{314 are} hydrogen atoms include a 1-methylene-2-propenyl group and a 2-methylene-3-butenyl group.

R ³¹¹ is a phenyl group, and R ³¹³ and R ^{314 are} hydrogen atoms such as 4- (1-phenylvinyl) phenyl group, 3- (1-phenylvinyl) phenyl group, 2- (1-phenylvinyl) A phenyl group etc. can be mention | raise | lifted.

^Examples of the group in which R ³¹¹ is a hydrogen atom, R ¹³ is a methyl group, and R ¹⁴ is a hydrogen atom include a 1-propenyl group, a crotyl group, a 4- (1-propenyl) phenyl group, and 4- (1-propenyl). ) Phenylmethyl group, 2- {4- (1-propenyl) phenyl} ethyl group, 3- (1-propenyl) phenyl group, 3- (1-propenyl) phenylmethyl group, 2- {3- (1-propenyl) ) Phenyl} ethyl group and the like.

（式中、Ｒ^３１１は水素原子又はヒドロカルビル基を表し、ｎ^３は０又は１であり、Ｒ^３１２はヒドロカルビレン基を表す。） The group represented by the formula (31-V) is preferably a group represented by the following formula (31-V1).

(Wherein R ³¹¹ represents a hydrogen atom or a hydrocarbyl group, n ³ represents 0 or 1, and R ³¹² represents a hydrocarbylene group.)

The group represented by the formula (31-V1) is preferably a group in which R ³¹¹ is a hydrogen atom, such as vinyl group, 4-vinylphenyl group, 3-vinylphenyl group, (4-vinylphenyl) methyl group, 2 -(4-vinylphenyl) ethyl group, (3-vinylphenyl) methyl group, 2- (3-vinylphenyl) ethyl group; R ³¹¹ is a methyl group, such as 4-isopropenylphenyl group, 3-iso A propenylphenyl group, a (4-isopropenylphenyl) methyl group, a 2- (4-isopropenylphenyl) ethyl group, a (3-isopropenylphenyl) methyl group, a 2- (3-isopropenylphenyl) ethyl group; R ³¹¹ As a group in which is a vinyl group, a 1-methylene-2-propenyl group, a 2-methylene-3-butenyl group; a group in which R ³¹¹ is a phenyl group, 4- (1-Phenylvinyl) phenyl group.

The group represented by the formula (31-V1) is more preferably a vinyl group.

S ³⁰¹ in the formula (31) represents a substituted silyl group.

^Examples of the substituted silyl group represented by S ³⁰¹ include a silyl group in which a hydrogen atom bonded to a silicon atom is substituted with a substituent such as an optionally substituted hydrocarbyl group, hydrocarbyloxy group, or substituted amino group. be able to. The substituents bonded to the silicon atom may be the same or different.

（式中、Ｘ^３０１、Ｘ^３０２及びＸ^３０３は、それぞれ独立に、置換アミノ基、又は、置換基を有していてもよいヒドロカルビル基を表し、Ｘ^３０１、Ｘ^３０２及びＸ^３０３の少なくとも１つが置換アミノ基である。） The substituted silyl group represented by S ³⁰¹ is preferably a group represented by the following formula (31-S).

( ^Wherein X ³⁰¹ , X ³⁰² and X ³⁰³ each independently represent a substituted amino group or a hydrocarbyl group which may have a substituent, wherein at least one of X ³⁰¹ , X ³⁰² and X ³⁰³ is A substituted amino group.)

The hydrocarbyl group optionally having a substituent of X ³⁰¹ , X ³⁰² and X ³⁰³ is a hydrocarbyl group optionally having at least one selected from the group consisting of an oxygen atom, a nitrogen atom and a silicon atom Can give.

^Examples of the hydrocarbyl group of X ³⁰¹ , X ³⁰² and X ³⁰³ include an alkyl group, an alkenyl group, an alkynyl group, an aryl group and an aralkyl group. Examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, and tert-butyl group. Examples of the alkenyl group include a vinyl group, an allyl group, a 1-propenyl group, and a 1-methylethenyl group. Examples of the alkynyl group include an ethynyl group and a propargyl group. Examples of the aryl group include a phenyl group, a tolyl group, and a xylyl group. Examples of the aralkyl group include a benzyl group. The hydrocarbyl group is preferably an alkyl group.

Examples of the hydrocarbyl group having an oxygen atom of X ³⁰¹ , X ³⁰² and X ³⁰³ include alkoxyalkyl groups such as a methoxymethyl group, a methoxyethyl group, an ethoxymethyl group and an ethoxyethyl group.

Examples of the hydrocarbyl group having a nitrogen atom of X ³⁰¹ , X ³⁰² and X ³⁰³ include dialkylaminoalkyl groups such as dimethylaminomethyl group, dimethylaminoethyl group, diethylaminomethyl group and diethylaminoethyl group.

Examples of the hydrocarbyl group having a silicon atom of X ³⁰¹ , X ³⁰² and X ³⁰³ include trialkylsilylalkyl groups such as trimethylsilylmethyl group, trimethylsilylethyl group, triethylsilylmethyl group and triethylsilylethyl group.

The number of carbon atoms of the hydrocarbyl group which may have a substituent of X ³⁰¹ , X ³⁰² and X ³⁰³ is preferably 1 to 10, more preferably 1 to 4.

The hydrocarbyl group which may have a substituent of X ³⁰¹ , X ³⁰² and X ³⁰³ is preferably an alkyl group or an alkoxyalkyl group. The alkyl group is preferably an alkyl group having 1 to 4 carbon atoms, more preferably a methyl group or an ethyl group. The alkoxyalkyl group is preferably an alkoxyalkyl group having 2 to 4 carbon atoms.

（式中、Ｒ^３１５及びＲ^３１６は、それぞれ、ヒドロカルビル基、又は、トリヒドロカルビルシリル基、あるいは、Ｒ^３１５とＲ^３１６とが結合して、窒素原子及び／又は酸素原子をヘテロ原子として有していてもよいヒドロカルビレン基、又は、Ｒ^３１５とＲ^３１６は１つの基であって、窒素原子に二重結合で結合する基を表す。） The substituted amino group for X ³⁰¹ , X ³⁰² and X ³⁰³ is preferably a group represented by the following formula (31-X).

(In the formula, each of R ³¹⁵ and R ³¹⁶ has a hydrocarbyl group, a trihydrocarbyl silyl group, or R ³¹⁵ and R ³¹⁶ bonded to each other, and has a nitrogen atom and / or an oxygen atom as a hetero atom. The hydrocarbylene group which may be substituted, or R ³¹⁵ and R ³¹⁶ are one group and represent a group bonded to the nitrogen atom with a double bond.)

^Examples of the hydrocarbyl group of R ³¹⁵ and R ³¹⁶ include an alkyl group, an alkenyl group, an alkynyl group, an aryl group, and an aralkyl group. Examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, and tert-butyl group. Examples of the alkenyl group include a vinyl group, an allyl group, a 1-propenyl group, and a 1-methylethenyl group. Examples of the alkynyl group include an ethynyl group and a propargyl group. Examples of the aryl group include a phenyl group, a tolyl group, and a xylyl group. Examples of the aralkyl group include a benzyl group.

The number of carbon atoms of the hydrocarbyl group of R ³¹⁵ and R ³¹⁶ is preferably 1 to 10, more preferably 1 to 4, and still more preferably 1 to 2.

The hydrocarbyl group of R ³¹⁵ and R ³¹⁶ is preferably an alkyl group, more preferably a linear alkyl group.

The trihydrocarbyl silyl group R ³¹⁵ and R ^316, may be mentioned trimethylsilyl group, triethylsilyl group, triisopropylsilyl group, a trialkylsilyl group such as tert- butyldimethylsilyl group.

The trihydrocarbyl silyl group R ³¹⁵ and R ^316, preferably a trialkylsilyl group having a carbon number of 3 to 9, more preferably an alkyl group bonded to the silicon atoms of 1 to 3 carbon atoms A trialkylsilyl group which is an alkyl group, and more preferably a trimethylsilyl group.

The hydrocarbylene group optionally having a nitrogen atom and / or an oxygen atom to which R ³¹⁵ and R ³¹⁶ are bonded as a hetero atom includes a hydrocarbylene group, a hydrocarbylene group having a nitrogen atom, and an oxygen atom. And hydrocarbylene groups. Examples of the hydrocarbylene group include an alkylene group such as an ethylene group, a trimethylene group, a tetramethylene group, a pentamethylene group, and a hexamethylene group. As the hydrocarbylene group having a nitrogen atom, a group represented by —CH ₂ CH ₂ —NH—CH ₂ —, a group represented by —CH ₂ CH ₂ —N═CH—, —CH═CH—N A group represented by ═CH— and a group represented by —CH ₂ CH ₂ —NH—CH ₂ CH ₂ — can be exemplified. Examples of the hydrocarbylene group having an oxygen atom include a group represented by —CH ₂ CH ₂ —O—CH ₂ CH ₂ —.

The number of carbon atoms of the hydrocarbylene group which may have a nitrogen atom and / or an oxygen atom to which R ³¹⁵ and R ³¹⁶ are bonded as a hetero atom is preferably 2 to 20, more preferably 2 to 7. Yes, more preferably 4-6.

The hydrocarbylene group which may have a nitrogen atom and / or oxygen atom to which R ³¹⁵ and R ³¹⁶ are bonded as a hetero atom is preferably a hydrocarbylene group, more preferably an alkylene group, A polymethylene group is preferred.

Examples of one group in which R ³¹⁵ and R ³¹⁶ are bonded to the nitrogen atom with a double bond include ethylidene group, propylidene group, butylidene group, 1-methylethylidene group, 1-methylpropylidene group, 1,3-dimethylbutylidene And hydrocarbylidene groups such as groups.

The number of carbon atoms of one group in which R ³¹⁵ and R ³¹⁶ are bonded to the nitrogen atom with a double bond is preferably 2 to 20, and more preferably 2 to 6.

R ³¹⁵ and R ³¹⁶ are preferably an alkyl group, a trialkylsilyl group, an alkylene group in which R ³¹⁵ and R ³¹⁶ are bonded, and more preferably an alkyl group.

Examples of the group represented by the formula (31-X) include an acyclic amino group and a cyclic amino group.

Examples of the acyclic amino group include a dialkylamino group and a bis (trialkylsilyl) amino group. Dialkylamino groups include dimethylamino, diethylamino, di (n-propyl) amino, di (isopropyl) amino, di (n-butyl) amino, di (sec-butyl) amino, di (tert -Butyl) amino group and ethylmethylamino group can be mentioned. Examples of the bis (trialkylsilyl) amino group include a bis (trimethylsilyl) amino group and a bis (t-butyldimethylsilyl) amino group.

Examples of the acyclic amino group include an ethylideneamino group, a 1-methylpropylideneamino group, a 1,3-dimethylbutylideneamino group, a 1-methylethylideneamino group, and a 4-N, N-dimethylaminobenzylideneamino group. You can also give it.

Examples of the cyclic amino group include 1-aziridinyl group, 1-azetidinyl group, 1-pyrrolidinyl group, 1-piperidinyl group, 1-hexamethyleneimino group, 1-heptamethyleneimino group, 1-octamethyleneimino group, 1-decamidine group. Examples thereof include 1-polymethyleneimino groups such as a methyleneimino group and 1-dodecamethyleneimino group. Moreover, 1-pyrrolyl group, 1-pyrazolidinyl group, 1-imidazolidinyl group, 1-pyrazolyl group, 1-imidazolyl group, 4,5-dihydro-1-imidazolyl group, 1-piperazinyl group and morpholino group are exemplified.

The group represented by the formula (31-X) is preferably an acyclic amino group, and more preferably a dialkylamino group. The dialkylamino group is preferably a dimethylamino group, a diethylamino group, a di (n-propyl) amino group, or a di (n-butyl) amino group, and more preferably a dimethylamino group or a diethylamino group.

In formula (31-S), at least one of X ³⁰¹ , X ³⁰² and X ³⁰³ is a substituted amino group, preferably two or more of X ³⁰¹ , X ³⁰² and X ³⁰³ are substituted amino groups, and more Preferably, two of X ³⁰¹ , X ³⁰² and X ³⁰³ are substituted amino groups.

As a compound represented by Formula (31), V ³⁰¹ is a group represented by Formula (31-V1), S ³⁰¹ is a group represented by Formula (31-S), and Formula (31- Examples of the compound in which R ^{311 in} V1) is a hydrogen atom and one of X ³⁰¹ , X ³⁰² and X ³⁰³ in formula (31-S) is a dialkylamino group include the following compounds.

Compound in which n ^{3 in} formula (31-V1) is 0:
(Dimethylamino) dimethylvinylsilane,
(Diethylamino) dimethylvinylsilane,
(Di-n-propylamino) dimethylvinylsilane,
(Di-n-butylamino) dimethylvinylsilane,
(Dimethylamino) diethylvinylsilane,
(Diethylamino) diethylvinylsilane,
(Di-n-propylamino) diethylvinylsilane,
(Di-n-butylamino) diethylvinylsilane.

Compound in which n ^{3 in} formula (31-V1) is 1:
(Dimethylamino) dimethyl-4-vinylphenylsilane,
(Dimethylamino) dimethyl-3-vinylphenylsilane,
(Diethylamino) dimethyl-4-vinylphenylsilane,
(Diethylamino) dimethyl-3-vinylphenylsilane,
(Di-n-propylamino) dimethyl-4-vinylphenylsilane,
(Di-n-propylamino) dimethyl-3-vinylphenylsilane,
(Di-n-butylamino) dimethyl-4-vinylphenylsilane,
(Di-n-butylamino) dimethyl-3-vinylphenylsilane,
(Dimethylamino) diethyl-4-vinylphenylsilane,
(Dimethylamino) diethyl-3-vinylphenylsilane,
(Diethylamino) diethyl-4-vinylphenylsilane,
(Diethylamino) diethyl-3-vinylphenylsilane,
(Di-n-propylamino) diethyl-4-vinylphenylsilane,
(Di-n-propylamino) diethyl-3-vinylphenylsilane,
(Di-n-butylamino) diethyl-4-vinylphenylsilane,
(Di-n-butylamino) diethyl-3-vinylphenylsilane.

As a compound represented by Formula (31), V ³⁰¹ is a group represented by Formula (31-V1), S ³⁰¹ is a group represented by Formula (31-S), and Formula (31- Examples of the compound in which R ^{311 in} V1) is a hydrogen atom and two of X ³⁰¹ , X ³⁰² and X ³⁰³ in formula (31-S) are dialkylamino groups include the following compounds.

Compound in which n ^{3 in} formula (31-V1) is 0:
Bis (dimethylamino) methylvinylsilane,
Bis (diethylamino) methylvinylsilane,
Bis (di-n-propylamino) methylvinylsilane,
Bis (di-n-butylamino) methylvinylsilane,
Bis (dimethylamino) ethylvinylsilane,
Bis (diethylamino) ethylvinylsilane,
Bis (di-n-propylamino) ethylvinylsilane,
Bis (di-n-butylamino) ethylvinylsilane.

Compound in which n ^{3 in} formula (31-V1) is 1:
Bis (dimethylamino) methyl-4-vinylphenylsilane,
Bis (dimethylamino) methyl-3-vinylphenylsilane,
Bis (diethylamino) methyl-4-vinylphenylsilane,
Bis (diethylamino) methyl-3-vinylphenylsilane,
Bis (di-n-propylamino) methyl-4-vinylphenylsilane,
Bis (di-n-propylamino) methyl-3-vinylphenylsilane,
Bis (di-n-butylamino) methyl-4-vinylphenylsilane,
Bis (di-n-butylamino) methyl-3-vinylphenylsilane,
Bis (dimethylamino) ethyl-4-vinylphenylsilane,
Bis (dimethylamino) ethyl-3-vinylphenylsilane,
Bis (diethylamino) ethyl-4-vinylphenylsilane,
Bis (diethylamino) ethyl-3-vinylphenylsilane,
Bis (di-n-propylamino) ethyl-4-vinylphenylsilane,
Bis (di-n-propylamino) ethyl-3-vinylphenylsilane,
Bis (di-n-butylamino) ethyl-4-vinylphenylsilane,
Bis (di-n-butylamino) ethyl-3-vinylphenylsilane.

As a compound represented by Formula (31), V ³⁰¹ is a group represented by Formula (31-V1), S ³⁰¹ is a group represented by Formula (31-S), and Formula (31- Examples of the compound in which R ^{311 in} V1) is a methyl group and two of X ³⁰¹ , X ³⁰² and X ³⁰³ in formula (31-S) are dialkylamino groups include the following compounds.

Compound in which n ^{3 in} formula (31-V1) is 1:
Bis (dimethylamino) methyl-4-isopropenylphenylsilane,
Bis (dimethylamino) methyl-3-isopropenylphenylsilane,
Bis (diethylamino) methyl-4-isopropenylphenylsilane,
Bis (diethylamino) methyl-3-isopropenylphenylsilane,
Bis (di-n-propylamino) methyl-4-isopropenylphenylsilane,
Bis (di-n-propylamino) methyl-3-isopropenylphenylsilane,
Bis (di-n-butylamino) methyl-4-isopropenylphenylsilane,
Bis (di-n-butylamino) methyl-3-isopropenylphenylsilane,
Bis (dimethylamino) ethyl-4-isopropenylphenylsilane,
Bis (dimethylamino) ethyl-3-isopropenylphenylsilane,
Bis (diethylamino) ethyl-4-isopropenylphenylsilane,
Bis (diethylamino) ethyl-3-isopropenylphenylsilane,
Bis (di-n-propylamino) ethyl-4-isopropenylphenylsilane,
Bis (di-n-propylamino) ethyl-3-isopropenylphenylsilane,
Bis (di-n-butylamino) ethyl-4-isopropenylphenylsilane,
Bis (di-n-butylamino) ethyl-3-isopropenylphenylsilane.

As a compound represented by Formula (31), V ³⁰¹ is a group represented by Formula (31-V1), S ³⁰¹ is a group represented by Formula (31-S), and Formula (31- Examples of the compound in which R ^{311 in} V1) is a vinyl group and two of X ³⁰¹ , X ^302, and X ³⁰³ in formula (31-S) are dialkylamino groups include the following compounds.

Compound in which n ^{3 in} formula (31-V1) is 0:
Bis (dimethylamino) methyl (1-methylene-2-propenyl) silane,
Bis (diethylamino) methyl (1-methylene-2-propenyl) silane,
Bis (di-n-propylamino) methyl (1-methylene-2-propenyl) silane,
Bis (di-n-butylamino) methyl (1-methylene-2-propenyl) silane,
Bis (dimethylamino) ethyl (1-methylene-2-propenyl) silane,
Bis (diethylamino) ethyl (1-methylene-2-propenyl) silane,
Bis (di-n-propylamino) ethyl (1-methylene-2-propenyl) silane,
Bis (di-n-butylamino) ethyl (1-methylene-2-propenyl) silane.

As a compound represented by Formula (31), V ³⁰¹ is a group represented by Formula (31-V1), S ³⁰¹ is a group represented by Formula (31-S), and Formula (31- Examples of the compound in which R ^{311 in} V1) is a phenyl group and two of X ³⁰¹ , X ³⁰² and X ³⁰³ in formula (31-S) are dialkylamino groups include the following compounds.

Compound in which n ^{3 in} formula (31-V1) is 1:
1- (4-bis (dimethylamino) methylsilyl) -1-phenylethylene,
1- (4-bis (diethylamino) methylsilyl) -1-phenylethylene,
1- (4-bis (di-n-propylamino) methylsilyl) -1-phenylethylene,
1- (4-bis (di-n-butylamino) methylsilyl) -1-phenylethylene,
1- (4-bis (dimethylamino) ethylsilyl) -1-phenylethylene,
1- (4-bis (diethylamino) ethylsilyl) -1-phenylethylene,
1- (4-bis (di-n-propylamino) ethylsilyl) -1-phenylethylene,
1- (4-Bis (di-n-butylamino) ethylsilyl) -1-phenylethylene.

As a compound represented by Formula (31), V ³⁰¹ is a group represented by Formula (31-V1), S ³⁰¹ is a group represented by Formula (31-S), and Formula (31- Examples of the compound in which R ^{311 in} V1) is a hydrogen atom and three of X ³⁰¹ , X ³⁰² and X ³⁰³ in formula (31-S) are dialkylamino groups include the following compounds.

Compound in which n ^{3 in} formula (31-V1) is 0:
Tris (dimethylamino) vinylsilane,
Tris (diethylamino) vinylsilane,
Tris (di-n-propylamino) vinylsilane,
Tris (di-n-butylamino) vinylsilane.

Compound in which n ^{3 in} formula (31-V1) is 1:
Tris (dimethylamino) -4-vinylphenylsilane,
Tris (dimethylamino) -3-vinylphenylsilane,
Tris (diethylamino) -4-vinylphenylsilane,
Tris (diethylamino) -3-vinylphenylsilane,
Tris (di-n-propylamino) -4-vinylphenylsilane,
Tris (di-n-propylamino) -3-vinylphenylsilane,
Tris (di-n-butylamino) -4-vinylphenylsilane,
Tris (di-n-butylamino) -3-vinylphenylsilane.

As a compound represented by Formula (31), V ³⁰¹ is a group represented by Formula (31-V1), S ³⁰¹ is a group represented by Formula (31-S), and Formula (31- Examples of the compound in which R ^{311 in} V1) is a methyl group and three of X ³⁰¹ , X ³⁰² and X ³⁰³ in formula (31-S) are dialkylamino groups include the following compounds.

Compound in which n ^{3 in} formula (31-V1) is 1:
Tris (dimethylamino) -4-isopropenylphenylsilane,
Tris (dimethylamino) -3-isopropenylphenylsilane,
Tris (diethylamino) -4-isopropenylphenylsilane,
Tris (diethylamino) -3-isopropenylphenylsilane,
Tris (di-n-propylamino) -4-isopropenylphenylsilane,
Tris (di-n-propylamino) -3-isopropenylphenylsilane,
Tris (di-n-butylamino) -4-isopropenylphenylsilane,
Tris (di-n-butylamino) -3-isopropenylphenylsilane.

As a compound represented by Formula (31), V ³⁰¹ is a group represented by Formula (31-V1), S ³⁰¹ is a group represented by Formula (31-S), and Formula (31- As the compound in which R ^{311 in} V1) is a vinyl group and three of X ³⁰¹ , X ³⁰² and X ³⁰³ in formula (31-S) are dialkylamino groups, the following compounds can be exemplified.

Compound in which n ^{3 in} formula (31-V1) is 0:
Tris (dimethylamino) (1-methylene-2-propenyl) silane,
Tris (diethylamino) (1-methylene-2-propenyl) silane,
Tris (di-n-propylamino) (1-methylene-2-propenyl) silane,
Tris (di-n-butylamino) (1-methylene-2-propenyl) silane.

As a compound represented by Formula (31), V ³⁰¹ is a group represented by Formula (31-V1), S ³⁰¹ is a group represented by Formula (31-S), and Formula (31- Examples of the compound in which R ^{311 in} V1) is a phenyl group and three of X ³⁰¹ , X ³⁰² and X ³⁰³ in formula (31-S) are dialkylamino groups include the following compounds.

Compound in which n ^{3 in} formula (31-V1) is 1:
1- (4-tris (dimethylamino) silyl) -1-phenylethylene,
1- (4-tris (diethylamino) silyl) -1-phenylethylene,
1- (4-Tris (di-n-propylamino) methylsilyl) -1-phenylethylene, 1- (4-tris (di-n-butylamino) methylsilyl) -1-phenylethylene.

The compound represented by formula (31) is preferably a compound in which V ³⁰¹ is a group represented by formula (31-V1) and S ³⁰¹ is a group represented by formula (31-S). More preferably, a compound in which two of X ³⁰¹ , X ³⁰² and X ³⁰³ in formula (31-S) are dialkylamino groups, and more preferably, R ³¹¹ in formula (31-V1) is A compound which is a hydrogen atom and n ³ in the formula (31-V1) is 0. Particularly preferred is a compound in which the remaining one of X ³⁰¹ , X ³⁰² and X ³⁰³ is an alkyl group or an alkoxyalkyl group. Most preferably,
Bis (dimethylamino) methylvinylsilane,
Bis (diethylamino) methylvinylsilane,
Bis (di-n-propylamino) methylvinylsilane,
Bis (di-n-butylamino) methylvinylsilane,
Bis (dimethylamino) ethylvinylsilane,
Bis (diethylamino) ethylvinylsilane,
Bis (di-n-propylamino) ethylvinylsilane,
Bis (di-n-butylamino) ethylvinylsilane.

V ³⁰² in the formula (32) represents a hydrocarbyl group having a polymerizable carbon-carbon double bond.

V ³⁰² is preferably a group represented by the following formula (32-V).

（式中、ｍ^３は０又は１であり、Ｒ^３２１、Ｒ^３２３及びＲ^３２４は、それぞれ独立に水素原子又はヒドロカルビル基を表し、Ｒ^３２２はヒドロカルビレン基を表す。）

(In the formula, m ³ is 0 or 1, R ³²¹ , R ³²³ and R ³²⁴ each independently represent a hydrogen atom or a hydrocarbyl group, and R ³²² represents a hydrocarbylene group.)

In the formula (32-V), m ³ represents 0 or 1.

^Examples of the hydrocarbyl group of R ³²¹ , R ³²³ and R ³²⁴ include an alkyl group, an alkenyl group, and an aryl group. Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, and a tert-butyl group, and a methyl group is preferable. Examples of the alkenyl group include a vinyl group, an allyl group, a 1-propenyl group, and a 1-methylethenyl group, and a vinyl group is preferable. Examples of the aryl group include a phenyl group, a methylphenyl group, and an ethylphenyl group, and a phenyl group is preferable.

R ³²¹ , R ³²³ and R ³²⁴ are preferably a hydrogen atom, a methyl group, a vinyl group or a phenyl group, more preferably a hydrogen atom.

^Examples of the hydrocarbylene group for R ³²² include an alkylene group, an arylene group, and a group in which an arylene group and an alkylene group are bonded.

Examples of the alkylene group include a methylene group, an ethylene group, and a trimethylene group. Preferably, it is a methylene group or an ethylene group. Examples of the arylene group include a phenylene group, a naphthylene group, and a biphenylene group. A phenylene group is preferred. More preferred are a para-phenylene group and a meta-phenylene group.

Examples of the group in which an arylene group and an alkylene group are bonded include a group in which a phenylene group and an alkylene group are bonded, a group in which a naphthylene group and an alkylene group are bonded, and a group in which a biphenylene group and an alkylene group are bonded. .
Moreover, as the group in which the arylene group and the alkylene group are bonded, it is preferable that the carbon atom of the arylene group of the group is bonded to the carbon atom to which R ³²¹ of the formula (32-V) is bonded.

In a group in which a phenylene group and an alkylene group are bonded (phenylene-alkylene group (for example, a group represented by the following formula (32-R))), the position of a carbon atom on the benzene ring from which a hydrogen atom has been removed; Depending on the position of the carbon atom on the benzene ring to which the alkylene group is bonded, a para-phenylene-alkylene group (for example, a group represented by the following formula (32-Ra)), a meta-phenylene-alkylene group (for example, A group represented by the following formula (32-Rb)), and an ortho-phenylene-alkylene group (for example, a group represented by the following formula (32-Rc)).

（式中、ｈ^３は１〜１０の整数を表し、（ＣＨ_２）_ｈ３はベンゼン環上の置換基である。）

(In the formula, h ³ represents an integer of 1 to 10, and (CH ₂ ) _{h 3} is a substituent on the benzene ring.)

（式中、ｉ^３、ｊ^３、ｋ^３は、それぞれ、１〜１０の整数を表す。）

(Wherein i ³ , j ³ and k ³ each represents an integer of 1 to 10)

^{H 3} of the formula (32-R), ^{i 3} of the formula (32-Ra), ^{j 3} of the formula (32-Rb), ^{k 3} of the formula (32-Rc) is preferably 1 to 5, more Preferably it is 1-2, More preferably, it is 1.

The group in which an arylene group and an alkylene group are bonded is preferably a group in which a phenylene group and an alkylene group are bonded, and more preferably a group represented by the above formula (32-Ra) or the above formula (32 -Rb), more preferably a para-phenylene-methylene group (a group represented by the formula (32-Ra) where i ³ = 1), a meta-phenylene-methylene group (j ³ = A group represented by the formula (32-Rb) in which = 1, para-phenylene-ethylene group (a group represented by the formula (32-Ra) in which i ³ = 2), a meta-phenylene-ethylene group ( a group represented by the formula (32-Rb) in which j ³ = 2), particularly preferably a para-phenylene-methylene group (a group represented by the formula (32-Ra) in which i ³ = 1). , meta - methylene group ^(j 3 = 1 - phenylene That is a formula (32-Rb) a group represented by).

Examples of the group represented by the formula (32-V) include the following groups.

As the group in which R ³²¹ , R ³²³ and R ³²⁴ are hydrogen atoms, a vinyl group, a vinylmethyl group, a vinylethyl group, a 4-vinylphenyl group, a 3-vinylphenyl group, a (4-vinylphenyl) methyl group, 2- ( 4-vinylphenyl) ethyl group, (3-vinylphenyl) methyl group, 2- (3-vinylphenyl) ethyl group and the like can be mentioned.

^Examples of the group in which R ³²¹ is a methyl group and R ³²³ and R ³²⁴ are hydrogen atoms include an isopropenyl group, a methallyl group, a 4-isopropenylphenyl group, a 3-isopropenylphenyl group, and (4-isopropenylphenyl) methyl. Group, 2- (4-isopropenylphenyl) ethyl group, (3-isopropenylphenyl) methyl group, 2- (3-isopropenylphenyl) ethyl group and the like.

^Examples of the group in which R ³²¹ is a vinyl group and R ³²³ and R ³²⁴ are hydrogen atoms include a 1-methylene-2-propenyl group and a 2-methylene-3-butenyl group.

^Examples of groups in which R ³²¹ is a phenyl group and R ³²³ and R ³²⁴ are hydrogen atoms include 4- (1-phenylvinyl) phenyl group, 3- (1-phenylvinyl) phenyl group, and 2- (1-phenylvinyl). ) A phenyl group can be mentioned.

^Examples of the group in which R ³²¹ is a hydrogen atom, R ³²³ is a methyl group, and R ³²⁴ is a hydrogen atom include 1-propenyl group, crotyl group, 4- (1-propenyl) phenyl group, 4- (1-propenyl group) ) Phenylmethyl group, 2- {4- (1-propenyl) phenyl} ethyl group, 3- (1-propenyl) phenyl group, 3- (1-propenyl) phenylmethyl group, 2- {3- (1-propenyl) ) Phenyl} ethyl group and the like.

（式中、Ｒ^３２１は水素原子又はヒドロカルビル基を表し、ｍ^３は０又は１であり、Ｒ^３２２はヒドロカルビレン基を表す。） The group represented by the formula (32-V) is preferably a group represented by the following formula (32-V1).

(Wherein R ³²¹ represents a hydrogen atom or a hydrocarbyl group, m ³ represents 0 or 1, and R ³²² represents a hydrocarbylene group.)

As the group represented by the formula (32-V1), a group in which R ³²¹ is a hydrogen atom is preferably a vinyl group, a 4-vinylphenyl group, a 3-vinylphenyl group, a (4-vinylphenyl) methyl group, 2 -(4-vinylphenyl) ethyl group, (3-vinylphenyl) methyl group, 2- (3-vinylphenyl) ethyl group; R ³²¹ is a methyl group, such as 4-isopropenylphenyl group, 3-iso Propenylphenyl, (4-isopropenylphenyl) methyl, 2- (4-isopropenylphenyl) ethyl, (3-isopropenylphenyl) methyl, 2- (3-isopropenylphenyl) ethyl; R ³²¹ As a group in which is a vinyl group, a 1-methylene-2-propenyl group, a 2-methylene-3-butenyl group; a group in which R ³²¹ is a phenyl group, 4- (1-Phenylvinyl) phenyl group.

The group represented by the formula (32-V1) is more preferably a vinyl group, (4-vinylphenyl) ethyl group, or (3-vinylphenyl) ethyl group in which ^R321 is a hydrogen atom.

In formula (32), A ³⁰² represents a substituted amino group or a nitrogen-containing heterocyclic group.

（式中、Ｒ^３２５及びＲ^３２６は、それぞれ、ヒドロカルビル基、又は、トリヒドロカルビルシリル基、あるいは、Ｒ^３２５とＲ^３２６とが結合して、窒素原子及び／又は酸素原子をヘテロ原子として有していてもよいヒドロカルビレン基、又は、Ｒ^３２５とＲ^３２６は１つの基であって、窒素原子に二重結合で結合する基を表す。） The substituted amino group for A ³⁰² is preferably a group represented by the following formula (32-A).

(In the formula, R ³²⁵ and R ³²⁶ each have a hydrocarbyl group, a trihydrocarbyl silyl group, or R ³²⁵ and R ³²⁶ bonded to each other and have a nitrogen atom and / or an oxygen atom as a hetero atom. The hydrocarbylene group which may be substituted, or R ³²⁵ and R ³²⁶ are one group and represent a group bonded to the nitrogen atom with a double bond.)

^Examples of the hydrocarbyl group of R ³²⁵ and R ³²⁶ include an alkyl group, an alkenyl group, an alkynyl group, an aryl group, and an aralkyl group. Examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, and tert-butyl group. Examples of the alkenyl group include a vinyl group, an allyl group, a 1-propenyl group, and a 1-methylethenyl group. Examples of the alkynyl group include an ethynyl group and a propargyl group. Examples of the aryl group include a phenyl group, a tolyl group, and a xylyl group. Examples of the aralkyl group include a benzyl group.

The number of carbon atoms of the hydrocarbyl group of R ³²⁵ and R ³²⁶ is preferably 1 to 10, more preferably 1 to 4, and still more preferably 1 to 2.

The hydrocarbyl group of R ³²⁵ and R ³²⁶ is preferably an alkyl group or an alkenyl group, more preferably an alkyl group, and still more preferably a linear alkyl group.

The trihydrocarbyl silyl group R ³²⁵ and R ^326, may be mentioned trimethylsilyl group, triethylsilyl group, triisopropylsilyl group, a trialkylsilyl group such as tert- butyldimethylsilyl group.

The trihydrocarbylsilyl group of R ³²⁵ and R ³²⁶ is preferably a trialkylsilyl group having 3 to 9 carbon atoms, more preferably an alkyl group bonded to a silicon atom having 1 to 4 carbon atoms. A trialkylsilyl group which is an alkyl group, and more preferably a trimethylsilyl group.

The hydrocarbylene group optionally having a nitrogen atom and / or an oxygen atom to which R ³²⁵ and R ³²⁶ are bonded as a hetero atom includes a hydrocarbylene group, a hydrocarbylene group having a nitrogen atom, and an oxygen atom. And hydrocarbylene groups. Examples of the hydrocarbylene group include an alkylene group such as an ethylene group, a trimethylene group, a tetramethylene group, a pentamethylene group, and a hexamethylene group. As the hydrocarbylene group having a nitrogen atom, a group represented by —CH ₂ CH ₂ —NH—CH ₂ —, a group represented by —CH ₂ CH ₂ —N═CH—, —CH═CH—N A group represented by ═CH— and a group represented by —CH ₂ CH ₂ —NH—CH ₂ CH ₂ — can be exemplified. Examples of the hydrocarbylene group having an oxygen atom include a group represented by —CH ₂ CH ₂ —O—CH ₂ CH ₂ —.

The number of carbon atoms of the hydrocarbylene group which may have a nitrogen atom and / or an oxygen atom to which R ³²⁵ and R ³²⁶ are bonded as a hetero atom is preferably 2 to 20, more preferably 2 to 7. Yes, more preferably 4-6.

The hydrocarbylene group which may have a nitrogen atom and / or oxygen atom to which R ³²⁵ and R ³²⁶ are bonded as a hetero atom is preferably a hydrocarbylene group, more preferably an alkylene group, A polymethylene group is preferred.

One group in which R ³²⁵ and R ³²⁶ are bonded to the nitrogen atom with a double bond is ethylidene group, propylidene group, butylidene group, 1-methylethylidene group, 1-methylpropylidene group, 1,3-dimethylbutylidene. And hydrocarbylidene groups such as groups.

The number of carbon atoms of one group in which R ³²⁵ and R ³²⁶ are bonded to the nitrogen atom with a double bond is preferably 2 to 20, and more preferably 2 to 6.

R ³²⁵ and R ³²⁶ are preferably a hydrocarbyl group, a trihydrocarbyl silyl group, and a hydrocarbylene group to which R ³²⁵ and R ³²⁶ are bonded.

Examples of the group represented by the formula (32-A) include an acyclic amino group and a cyclic amino group.

Examples of the acyclic amino group include a dialkylamino group and a bis (trialkylsilyl) amino group. Dialkylamino groups include dimethylamino, diethylamino, di (n-propyl) amino, di (isopropyl) amino, di (n-butyl) amino, di (sec-butyl) amino, di (tert -Butyl) amino group and ethylmethylamino group can be mentioned. Examples of the bis (trialkylsilyl) amino group include a bis (trimethylsilyl) amino group and a bis (tert-butyldimethylsilyl) amino group.

The acyclic amino group further includes an ethylideneamino group, a 1-methylpropylideneamino group, a 1,3-dimethylbutylideneamino group, a 1-methylethylideneamino group, and a 4-N, N-dimethylaminobenzylideneamino group. You can also give it.

Examples of the cyclic amino group include 1-aziridinyl group, 1-azetidinyl group, 1-pyrrolidinyl group, 1-piperidinyl group, 1-hexamethyleneimino group, 1-imidazolyl group, 4,5-dihydro-1-imidazolyl group, 1 Examples include -pyrrolyl group, 1-pyrazolyl group, 1-imidazolidinyl group, 1-piperazinyl group, and morpholino group.

The group represented by the formula (32-A) is preferably a group in which R ³²⁵ and R ³²⁶ are hydrocarbyl groups, a group in which R ³²⁵ and R ³²⁶ are trihydrocarbyl silyl groups, and R ³²⁵ and R ³²⁶ are bonded. Group which is a hydrocarbylene group. More preferably, R ³²⁵ and R ³²⁶ are a group that is a linear alkyl group, R ³²⁵ and R ³²⁶ are a trialkylsilyl group, and a group that is a polymethylene group to which R ³²⁵ and R ³²⁶ are bonded.

More preferably, the group represented by the formula (32-A) is a dimethylamino group, a diethylamino group, a di (n-propyl) amino group, a di (n-butyl) amino group, a bis (trimethylsilyl) amino group, A bis (tert-butyldimethylsilyl) amino group, a 1-pyrrolidinyl group, a 1-piperidinyl group, and a 1-hexamethyleneimino group, particularly preferably a 1-pyrrolidinyl group.

^Examples of the nitrogen-containing heterocyclic group represented by A ³⁰² include a nitrogen-containing aliphatic heterocyclic group and a nitrogen-containing aromatic heterocyclic group. In the present specification, a nitrogen-containing aliphatic heterocyclic group represents a group obtained by removing one hydrogen atom from a carbon atom of a heterocyclic ring of a compound having a nitrogen-containing aliphatic heterocyclic ring. Represents an aliphatic heterocycle having a nitrogen atom as a heteroatom. The nitrogen-containing aromatic heterocyclic group represents a group obtained by removing one hydrogen atom from a carbon atom of a heterocyclic ring of a compound having a nitrogen-containing aromatic heterocyclic ring, and the nitrogen-containing aromatic heterocyclic ring constitutes a ring. An aromatic heterocyclic ring having a nitrogen atom as a hetero atom is represented.

As the nitrogen-containing aliphatic heterocyclic group represented by A ³⁰² , a group having only a nitrogen atom as a hetero atom constituting a ring, a group having a nitrogen atom and an oxygen atom as a hetero atom constituting a ring, and a hetero atom constituting a ring Examples thereof include a group having a nitrogen atom and a sulfur atom.

The nitrogen-containing aliphatic heterocyclic group having only a nitrogen atom as a hetero atom constituting the ring includes a group having an aziridine ring, a group having an azetidine ring, a group having a pyrrolidine ring, a group having a piperidine ring, a hexamethyleneimine ring , A group having an imidazolidine ring, a group having a piperazine ring, a group having a pyrazolidine ring, and the like.

Examples of the group having an aziridine ring include an N-alkyl-2-aziridinyl group.
Examples of the group having an azetidine ring include an N-alkyl-2-azetidinyl group and an N-alkyl-3-azetidinyl group.
Examples of the group having a pyrrolidine ring include an N-alkyl-2-pyrrolidinyl group and an N-alkyl-3-pyrrolidinyl group.
Examples of the group having a piperidine ring include an N-alkyl-2-piperidinyl group, an N-alkyl-3-piperidinyl group, and an N-alkyl-4-piperidinyl group.
Examples of the group having a hexamethyleneimine ring include an N-alkyl-2-hexamethyleneimino group, an N-alkyl-3-hexamethyleneimino group, and an N-alkyl-4-hexamethyleneimino group.
Examples of the group having an imidazolidine ring include a 1,3-dialkyl-2-imidazolidyl group and a 1,3-dialkyl-4-imidazolidyl group.
Examples of the group having a piperazine ring include a 1,4-dialkyl-2-piperazinyl group.
Examples of the group having a pyrazolidine ring include a 1,2-dialkyl-3-pyrazolidyl group and a 1,2-dialkyl-4-pyrazolidyl group.

Examples of the nitrogen-containing aliphatic heterocyclic group having a nitrogen atom and an oxygen atom as a hetero atom constituting the ring include a group having a morpholine ring and a group having an isoxazolidine ring.

Examples of the group having a morpholine ring include an N-alkyl-2-morpholino group and an N-alkyl-3-morpholino group.
Examples of the group having an isoxazolidine ring include an N-alkyl-3-isoxazolidinyl group, an N-alkyl-4-isoxazolidinyl group, and an N-alkyl-5-isoxazolidinyl group. Can do.

Examples of the nitrogen-containing aliphatic heterocyclic group having a nitrogen atom and a sulfur atom as hetero atoms constituting the ring include a group having a thiomorpholine ring and a group having an isothiazolidine ring.

Examples of the group having a thiomorpholine ring include an N-alkyl-2-thiomorpholino group and an N-alkyl-3-thiomorpholino group.
Examples of the group having an isothiazolidine ring include an N-alkyl-3-isothiazolidinyl group, an N-alkyl-4-isothiazolidinyl group, and an N-alkyl-5-isothiazolidinyl group.

The nitrogen-containing aliphatic heterocyclic group represented by A ³⁰² is preferably a group having only a nitrogen atom as a hetero atom constituting the ring. The number of carbon atoms in the nitrogen-containing aliphatic heterocyclic group is preferably 4-10.

As the nitrogen-containing aromatic heterocyclic group of A ³⁰² , a group having only a nitrogen atom as a hetero atom constituting a ring, a group having a nitrogen atom and an oxygen atom as a hetero atom constituting a ring, and a hetero atom constituting a ring Examples thereof include a group having a nitrogen atom and a sulfur atom.

The nitrogen-containing aromatic heterocyclic group having only a nitrogen atom as a hetero atom constituting the ring includes a group having a pyrrole ring, a group having an imidazole ring, a group having a pyrazole ring, a group having a pyridine ring, and a pyridazine ring. A group having a pyrimidine ring, a group having a pyrazine ring, a group having a quinoline ring, a group having an isoquinoline ring, a group having a cinnoline ring, a group having a quinazoline ring, a group having a phthalazine ring, and the like.

Examples of the group having a pyrrole ring include a 2-pyrrolyl group, a 3-pyrrolyl group, a 2- (N-methylpyrrolyl) group, and a 3- (N-methylpyrrolyl) group.
Examples of the group having an imidazole ring include 2-imidazolyl group, 4-imidazolyl group, 5-imidazolyl group, 2- (N-methylimidazolyl) group, 4- (N-methylimidazolyl) group, and 5- (N-methylimidazolyl). ) Group.
Examples of the group having a pyrazole ring include 3-pyrazolyl group, 4-pyrazolyl group, 5-pyrazolyl group, 3- (N-methylpyrazolyl) group, 4- (N-methylpyrazolyl) group, and 5- (N-methylpyrazolyl). ) Group.
Examples of the group having a pyridine ring include a 2-pyridyl group, a 3-pyridyl group, and a 4-pyridyl group.
Examples of the group having a pyridazine ring include a 3-pyridazyl group and a 4-pyridazyl group.
Examples of the group having a pyrimidine ring include a 2-pyrimidyl group, a 4-pyrimidyl group, and a 5-pyrimidyl group.
Examples of the group having a pyrazine ring include a 2-pyrazyl group.
Examples of the group having a quinoline ring include a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 5-quinolyl group, a 6-quinolyl group, a 7-quinolyl group, and an 8-quinolyl group.
Examples of the group having an isoquinoline ring include a 1-isoquinolyl group, a 3-isoquinolyl group, a 4-isoquinolyl group, a 5-isoquinolyl group, a 6-isoquinolyl group, a 7-isoquinolyl group, and an 8-isoquinolyl group.
Examples of the group having a cinnoline ring include a 3-cinnolinyl group, a 4-cinnolinyl group, a 5-cinnolinyl group, a 6-cinnolinyl group, a 7-cinnolinyl group, and an 8-cinnolinyl group.
Examples of the group having a quinazoline ring include a 2-quinazolinyl group, a 4-quinazolinyl group, a 5-quinazolinyl group, a 6-quinazolinyl group, a 7-quinazolinyl group, and an 8-quinazolinyl group.
Examples of the group having a phthalazine ring include a 1-phthalazinyl group, a 5-phthalazinyl group, and a 6-phthalazinyl group.
The nitrogen-containing aromatic heterocyclic group having only a nitrogen atom as a hetero atom constituting the ring is preferably a group having an imidazole ring, a group having a pyridine ring, or a group having a quinoline ring.

Examples of the nitrogen-containing aromatic heterocyclic group having a nitrogen atom and an oxygen atom as hetero atoms constituting the ring include a group having an oxazole ring and a group having an isoxazole ring.

Examples of the group having an oxazole ring include a 2-oxazolyl group, a 4-oxazolyl group, and a 5-oxazolyl group.
Examples of the group having an isoxazole ring include a 3-isoxazolyl group, a 4-isoxazolyl group, and a 5-isoxazolyl group.
The nitrogen-containing aromatic heterocyclic group having a nitrogen atom and an oxygen atom as hetero atoms constituting the ring is preferably a group having an oxazole ring.

Examples of the nitrogen-containing aromatic heterocyclic group having a nitrogen atom and a sulfur atom as the hetero atoms constituting the ring include a group having a thiazole ring, a group having an isothiazole ring, and the like.

Examples of the group having a thiazole ring include a 2-thiazolyl group, a 4-thiazolyl group, and a 5-thiazolyl group.
Examples of the group having an isothiazole ring include a 3-isothiazolyl group, a 4-isothiazolyl group, and a 5-isothiazolyl group.
The nitrogen-containing aromatic heterocyclic group having a nitrogen atom and a sulfur atom as a hetero atom constituting the ring is preferably a group having a thiazole ring.

The nitrogen-containing aromatic heterocyclic group represented by A ³⁰² is preferably a nitrogen-containing aromatic heterocyclic group having only a nitrogen atom as a hetero atom constituting the ring, more preferably a group having an imidazole ring or a pyridine ring. And a group having a quinoline ring, more preferably a group having a pyridine ring.

As a compound represented by the formula (32), V ³⁰² is a group represented by the formula (32-V1), R ³²¹ in the formula (32-V1) is a hydrogen atom, and m ³ is 0. As examples of the compound in which A ³⁰² is a substituted amino group, the following compounds can be given.

1-vinylpyrrolidine,
1-vinyl piperidine,
1-vinylhexamethyleneimine,
1-vinyl piperazine,
1-vinyl pyrrole,
1-vinylimidazole,
1-vinylpyrazole,
1-Vinylquinoline.

As a compound represented by the formula (32), V ³⁰² is a group represented by the formula (32-V1), R ³²¹ in the formula (32-V1) is a hydrogen atom, and m ³ is 1. In addition, examples of the compound in which R ³²² is a phenylene group and A ³⁰² is a substituted amino group include the following compounds.

4-N, N-dimethylaminostyrene,
4-N, N-diethylaminostyrene,
4-N, N-di-n-propylaminostyrene,
4-N, N-di-n-butylaminostyrene,
4-N, N-diallylaminostyrene,
4-N, N-bis (trimethylsilyl) aminostyrene,
4-N, N-bis (tert-butyldimethylsilyl) aminostyrene,
4- (1-aziridinyl) styrene,
4- (1-pyrrolidinyl) styrene,
4- (1-piperidinyl) styrene,
4- (1-hexamethyleneimino) styrene,
3-N, N-dimethylaminostyrene,
3-N, N-diethylaminostyrene,
3-N, N-di-n-propylaminostyrene,
3-N, N-di-n-butylaminostyrene,
3-N, N-diallylaminostyrene,
3-N, N-bis (trimethylsilyl) aminostyrene,
3-N, N-bis (tert-butyldimethylsilyl) aminostyrene,
3- (1-aziridinyl) styrene,
3- (1-pyrrolidinyl) styrene,
3- (1-piperidinyl) styrene,
3- (1-Hexamethyleneimino) styrene.

As a compound represented by the formula (32), V ³⁰² is a group represented by the formula (32-V1), R ³²¹ in the formula (32-V1) is a hydrogen atom, and m ³ is 1. In addition, examples of the compound in which R ³²² is a group represented by the formula (32-Ra) and A ³⁰² is a substituted amino group include the following compounds.

A compound in which i ^{3 of} formula (32-Ra) is 1:
4-N, N-dimethylaminomethylstyrene,
4-N, N-diethylaminomethylstyrene,
4-N, N-di-n-propylaminomethylstyrene,
4-N, N-di-n-butylaminomethylstyrene,
4-N, N-diallylaminomethylstyrene,
4-N, N-bis (trimethylsilyl) aminomethylstyrene,
4-N, N-bis (tert-butyldimethylsilyl) aminomethylstyrene,
4- (1-aziridinyl) methylstyrene,
4- (1-pyrrolidinyl) methylstyrene,
4- (1-piperidinyl) methylstyrene,
4- (1-Hexamethyleneimino) methylstyrene.

A compound in which i ^{3 of} formula (32-Ra) is 2:
4-N, N-dimethylaminoethylstyrene,
4-N, N-diethylaminoethylstyrene,
4-N, N-di-n-propylaminoethylstyrene,
4-N, N-di-n-butylaminoethylstyrene,
4-N, N-diallylaminoethylstyrene,
4-N, N-bis (trimethylsilyl) aminoethylstyrene,
4-N, N-bis (tert-butyldimethylsilyl) aminoethylstyrene,
4- (1-aziridinyl) ethylstyrene,
4- (1-piperidinyl) ethylstyrene,
4- (1-Hexamethyleneimino) ethylstyrene.

As a compound represented by the formula (32), V ³⁰² is a group represented by the formula (32-V1), R ³²¹ in the formula (32-V1) is a hydrogen atom, and m ³ is 1. In addition, examples of the compound in which R ³²² is a group represented by the formula (32-Rb) and A ³⁰² is a substituted amino group include the following compounds.

A compound in which j ^{3 of} formula (32-Rb) is 1:
3-N, N-dimethylaminomethylstyrene,
3-N, N-diethylaminomethylstyrene,
3-N, N-di-n-propylaminomethylstyrene,
3-N, N-di-n-butylaminomethylstyrene,
3-N, N-diallylaminomethylstyrene,
3-N, N-bis (trimethylsilyl) aminomethylstyrene,
3-N, N-bis (tert-butyldimethylsilyl) aminomethylstyrene,
3- (1-aziridinyl) methylstyrene,
3- (1-pyrrolidinyl) methylstyrene,
3- (1-piperidinyl) methylstyrene,
3- (1-Hexamethyleneimino) methylstyrene.

A compound in which j ^{3 of} formula (32-Rb) is 2:
3-N, N-dimethylaminoethylstyrene,
3-N, N-diethylaminoethylstyrene,
3-N, N-di-n-propylaminoethylstyrene,
3-N, N-di-n-butylaminoethylstyrene,
3-N, N-diallylaminoethylstyrene,
3-N, N-bis (trimethylsilyl) aminoethylstyrene,
3-N, N-bis (tert-butyldimethylsilyl) aminoethylstyrene,
3- (1-aziridinyl) ethylstyrene,
3- (1-piperidinyl) ethylstyrene,
3- (1-Hexamethyleneimino) ethylstyrene.

As a compound represented by Formula (32), V ³⁰² is a group represented by Formula (32-V1), R ³²¹ in Formula (32-V1) is a methyl group, and m ³ is 0. As examples of the compound in which A ³⁰² is a substituted amino group, the following compounds can be given.

1-isopropenylpyrrolidine,
1-isopropenyl piperidine,
1-isopropenyl hexamethyleneimine,
1-isopropenyl piperazine,
1-isopropenyl pyrrole,
1-isopropenylimidazole,
1-isopropenylpyrazole,
Isopropenyl quinoline.

As a compound represented by the formula (32), V ³⁰² is a group represented by the formula (32-V1), R ³²¹ in the formula (32-V1) is a methyl group, and m ³ is 1. In addition, examples of the compound in which R ³²² is a phenylene group and A ³⁰² is a substituted amino group include the following compounds.

4-N, N-dimethylaminoisopropenylbenzene,
4-N, N-diethylaminoisopropenylbenzene,
4-N, N-di-n-propylaminoisopropenylbenzene,
4-N, N-di-n-butylaminoisopropenylbenzene,
4-N, N-diallylaminoisopropenylbenzene,
4-N, N-bis (trimethylsilyl) aminoisopropenylbenzene,
4-N, N-bis (tert-butyldimethylsilyl) aminoisopropenylbenzene, 4- (1-aziridinyl) isopropenylbenzene,
4- (1-pyrrolidinyl) isopropenylbenzene,
4- (1-piperidinyl) isopropenylbenzene,
4- (1-hexamethyleneimino) isopropenylbenzene,
3-N, N-dimethylaminoisopropenylbenzene,
3-N, N-diethylaminoisopropenylbenzene,
3-N, N-di-n-propylaminoisopropenylbenzene,
3-N, N-di-n-butylaminoisopropenylbenzene,
3-N, N-diallylaminoisopropenylbenzene,
3-N, N-bis (trimethylsilyl) aminoisopropenylbenzene,
3-N, N-bis (tert-butyldimethylsilyl) aminoisopropenylbenzene, 3- (1-aziridinyl) isopropenylbenzene,
3- (1-pyrrolidinyl) isopropenylbenzene,
3- (1-piperidinyl) isopropenylbenzene,
3- (1-Hexamethyleneimino) isopropenylbenzene.

As a compound represented by the formula (32), V ³⁰² is a group represented by the formula (32-V1), R ³²¹ in the formula (32-V1) is a methyl group, and m ³ is 1. In addition, examples of the compound in which R ³²² is a group represented by the formula (32-Ra) and A ³⁰² is a substituted amino group include the following compounds.

A compound in which i ^{3 of} formula (32-Ra) is 1:
4-N, N-dimethylaminomethylisopropenylbenzene,
4-N, N-diethylaminomethylisopropenylbenzene,
4-N, N-di-n-propylaminomethylisopropenylbenzene,
4-N, N-di-n-butylaminomethylisopropenylbenzene,
4-N, N-diallylaminomethylisopropenylbenzene,
4-N, N-bis (trimethylsilyl) aminomethylisopropenylbenzene,
4-N, N-bis (tert-butyldimethylsilyl) aminomethylisopropenylbenzene,
4- (1-aziridinyl) methylisopropenylbenzene,
4- (1-pyrrolidinyl) methylisopropenylbenzene,
4- (1-piperidinyl) methyl isopropenylbenzene,
4- (1-Hexamethyleneimino) methylisopropenylbenzene.

A compound in which i ^{3 of} formula (32-Ra) is 2:
4-N, N-dimethylaminoethylisopropenylbenzene,
4-N, N-diethylaminoethylisopropenylbenzene,
4-N, N-di-n-propylaminoethylisopropenylbenzene,
4-N, N-di-n-butylaminoethylisopropenylbenzene,
4-N, N-diallylaminoethyl isopropenylbenzene,
4-N, N-bis (trimethylsilyl) aminoethylisopropenylbenzene,
4-N, N-bis (tert-butyldimethylsilyl) aminoethylisopropenylbenzene,
4- (1-aziridinyl) ethyl isopropenylbenzene,
4- (1-pyrrolidinyl) ethyl isopropenylbenzene,
4- (1-piperidinyl) ethyl isopropenylbenzene,
4- (1-Hexamethyleneimino) ethyl isopropenylbenzene.

As a compound represented by the formula (32), V ³⁰² is a group represented by the formula (32-V1), R ³²¹ in the formula (32-V1) is a methyl group, and m ³ is 1. In addition, examples of the compound in which R ³²² is a group represented by the formula (32-Rb) and A ³⁰² is a substituted amino group include the following compounds.

A compound in which j ^{3 of} formula (32-Rb) is 1:
3-N, N-dimethylaminomethylisopropenylbenzene,
3-N, N-diethylaminomethylisopropenylbenzene,
3-N, N-di-n-propylaminomethylisopropenylbenzene,
3-N, N-di-n-butylaminomethylisopropenylbenzene,
3-N, N-diallylaminomethylisopropenylbenzene,
3-N, N-bis (trimethylsilyl) aminomethylisopropenylbenzene,
3-N, N-bis (tert-butyldimethylsilyl) aminomethylisopropenylbenzene,
3- (1-aziridinyl) methyl isopropenylbenzene,
3- (1-pyrrolidinyl) methylisopropenylbenzene,
3- (1-piperidinyl) methylisopropenylbenzene,
3- (1-Hexamethyleneimino) methylisopropenylbenzene.

A compound in which j ^{3 of} formula (32-Rb) is 2:
3-N, N-dimethylaminoethylisopropenylbenzene,
3-N, N-diethylaminoethylisopropenylbenzene,
3-N, N-di-n-propylaminoethylisopropenylbenzene,
3-N, N-di-n-butylaminoethyl isopropenylbenzene,
3-N, N-diallylaminoethylisopropenylbenzene,
3-N, N-bis (trimethylsilyl) aminoethylisopropenylbenzene,
3-N, N-bis (tert-butyldimethylsilyl) aminoethylisopropenylbenzene,
3- (1-aziridinyl) ethyl isopropenylbenzene,
3- (1-pyrrolidinyl) ethyl isopropenylbenzene,
3- (1-piperidinyl) ethyl isopropenylbenzene,
3- (1-Hexamethyleneimino) ethyl isopropenylbenzene.

As a compound represented by Formula (32), V ³⁰² is a group represented by Formula (32-V1), R ³²¹ in Formula (32-V1) is a vinyl group, and m ³ is 0. As examples of the compound in which A ³⁰² is a substituted amino group, the following compounds can be given.

2-N, N-dimethylamino-1,3-butadiene,
2-N, N-diethylamino-1,3-butadiene,
2-N, N-di-n-propylamino-1,3-butadiene,
2-N, N-di-n-butylamino-1,3-butadiene,
2-N, N-diallylamino-1,3-butadiene,
2-N, N-bis (trimethylsilyl) amino-1,3-butadiene,
2-N, N-bis (tert-butyldimethylsilyl) amino-1,3-butadiene,
2- (1-aziridinyl) -1,3-butadiene,
2- (1-pyrrolidinyl) -1,3-butadiene,
2- (1-piperidinyl) -1,3-butadiene,
2- (1-hexamethyleneimino) -1,3-butadiene,
2- (1-pyrrolyl) -1,3-butadiene,
2- (1-imidazolyl) -1,3-butadiene,
2- (1-Pyrazolyl) -1,3-butadiene.

As a compound represented by the formula (32), V ³⁰² is a group represented by the formula (32-V1), R ³²¹ in the formula (32-V1) is a vinyl group, and m ³ is 1. In addition, examples of the compound in which R ³²² is an alkylene group and A ³⁰² is a substituted amino group include the following compounds.

Compound wherein R ³²² is a methylene group:
2-N, N-dimethylaminomethyl-1,3-butadiene,
2-N, N-diethylaminomethyl-1,3-butadiene,
2-N, N-di-n-propylaminomethyl-1,3-butadiene,
2-N, N-di-n-butylaminomethyl-1,3-butadiene,
2-N, N-diallylaminomethyl-1,3-butadiene,
2-N, N-bis (trimethylsilyl) aminomethyl-1,3-butadiene,
2-N, N-bis (tert-butyldimethylsilyl) aminomethyl-1,3-butadiene,
2- (1-aziridinyl) methyl-1,3-butadiene,
2- (1-pyrrolidinyl) methyl-1,3-butadiene,
2- (1-piperidinyl) methyl-1,3-butadiene,
2- (1-hexamethyleneimino) methyl-1,3-butadiene,
1- (2-methylene-3-butenyl) pyrrole,
1- (2-methylene-3-butenyl) imidazole,
1- (2-Methylene-3-butenyl) pyrazole.

A compound in which R ³²² is an ethylene group:
5-N, N-dimethylamino-3-methylene-1-pentene,
5-N, N-diethylamino-3-methylene-1-pentene,
5-N, N-di-n-propylamino-3-methylene-1-pentene,
5-N, N-di-n-butylamino-3-methylene-1-pentene,
5-N, N-diallylamino-3-methylene-1-pentene,
5-N, N-bis (trimethylsilyl) amino-3-methylene-1-pentene,
5-N, N-bis (tert-butyldimethylsilyl) amino-3-methylene-1-pentene,
5- (1-aziridinyl) -3-methylene-1-pentene,
5- (1-pyrrolidinyl) -3-methylene-1-pentene,
5- (1-piperidinyl) -3-methylene-1-pentene,
5- (1-hexamethyleneimino) -3-methylene-1-pentene,
1- (3-methylene-4-pentenyl) pyrrole,
1- (3-methylene-4-pentenyl) imidazole,
1- (3-methylene-4-pentenyl) pyrazole.

As a compound represented by the formula (32), V ³⁰² is a group represented by the formula (32-V1), R ³²¹ in the formula (32-V1) is a phenyl group, and m ³ is 1. In addition, examples of the compound in which R ³²² is a phenylene group and A ³⁰² is a substituted amino group include the following compounds.

1- (4-N, N-dimethylaminophenyl) -1-phenylethylene,
1- (4-N, N-diethylaminophenyl) -1-phenylethylene,
1- (4-N, N-dipropylaminophenyl) -1-phenylethylene,
1- (4-N, N-diisopropylaminophenyl) -1-phenylethylene,
1- (4-N, N-dibutylaminophenyl) -1-phenylethylene,
1- (4-N, N-diisobutylaminophenyl) -1-phenylethylene,
1- (4-N, N-di (tert-butyl) aminophenyl) -1-phenylethylene, 1- (4-N, N-diphenylaminophenyl) -1-phenylethylene,
1- (4- (1-aziridinyl) phenyl) -1-phenylethylene,
1- (4- (1-pyrrolidinyl) phenyl) -1-phenylethylene,
1- (4- (1-piperidinyl) phenyl) -1-phenylethylene,
1- (4-hexamethyleneiminophenyl) -1-phenylethylene,
1- (4-morpholinophenyl) -1-phenylethylene,
1- (4- (N, N-bis (trimethylsilyl) amino) phenyl) -1-phenylethylene,
1- (4- (N, N-bis (tert-butyldimethylsilyl) amino) phenyl) -1-phenylethylene,
1- (4- (N, N-bis (triisopropylsilyl) amino) phenyl) -1-phenylethylene,
1- (3-N, N-dimethylaminophenyl) -1-phenylethylene,
1- (3-N, N-diethylaminophenyl) -1-phenylethylene,
1- (3-N, N-dipropylaminophenyl) -1-phenylethylene,
1- (3-N, N-diisopropylaminophenyl) -1-phenylethylene,
1- (3-N, N-dibutylaminophenyl) -1-phenylethylene,
1- (3-N, N-diisobutylaminophenyl) -1-phenylethylene,
1- (3-N, N-di (tert-butyl) aminophenyl) -1-phenylethylene, 1- (3-N, N-diphenylaminophenyl) -1-phenylethylene,
1- (3- (1-aziridinyl) phenyl) -1-phenylethylene,
1- (3- (1-pyrrolidinyl) phenyl) -1-phenylethylene,
1- (3- (1-piperidinyl) phenyl) -1-phenylethylene,
1- (3-hexamethyleneiminophenyl) -1-phenylethylene,
1- (3-morpholinophenyl) -1-phenylethylene,
1- (3- (N, N-bis (trimethylsilyl) amino) phenyl) -1-phenylethylene,
1- (3- (N, N-bis (tert-butyldimethylsilyl) amino) phenyl) -1-phenylethylene,
1- (3- (N, N-bis (triisopropylsilyl) amino) phenyl) -1-phenylethylene.

As a compound represented by the formula (32), V ³⁰² is a group represented by the formula (32-V1), R ³²¹ in the formula (32-V1) is a phenyl group, and m ³ is 1. In addition, examples of the compound in which R ³²² is a group represented by the formula (32-Ra) and A ³⁰² is a substituted amino group include the following compounds.

A compound in which i ^{3 of} formula (32-Ra) is 1:
1- (4-N, N-dimethylaminomethylphenyl) -1-phenylethylene,
1- (4-N, N-diethylaminomethylphenyl) -1-phenylethylene,
1- (4-N, N-dipropylaminomethylphenyl) -1-phenylethylene,
1- (4-N, N-diisopropylaminomethylphenyl) -1-phenylethylene,
1- (4-N, N-dibutylaminomethylphenyl) -1-phenylethylene,
1- (4-N, N-diisobutylaminomethylphenyl) -1-phenylethylene,
1- (4-N, N-di (tert-butyl) aminomethylphenyl) -1-phenylethylene,
1- (4-N, N-diphenylaminomethylphenyl) -1-phenylethylene,
1- (4- (1-aziridinylmethyl) phenyl) -1-phenylethylene,
1- (4- (1-pyrrolidinylmethyl) phenyl) -1-phenylethylene,
1- (4- (1-piperidinylmethyl) phenyl) -1-phenylethylene,
1- (4-hexamethyleneiminomethylphenyl) -1-phenylethylene,
1- (4-morpholinomethylphenyl) -1-phenylethylene,
1- (4- (N, N-bis (trimethylsilyl) aminomethyl) phenyl) -1-phenylethylene,
1- (4- (N, N-bis (tert-butyldimethylsilyl) amino) methylphenyl) -1-phenylethylene,
1- (4- (N, N-bis (triisopropylsilyl) amino) methylphenyl) -1-phenylethylene.

As a compound represented by the formula (32), V ³⁰² is a group represented by the formula (32-V1), R ³²¹ in the formula (32-V1) is a phenyl group, and m ³ is 1. In addition, examples of the compound in which R ³²² is a group represented by the formula (32-Rb) and A ³⁰² is a substituted amino group include the following compounds.

A compound in which j ^{3 of} formula (32-Rb) is 1:
1- (3-N, N-dimethylaminomethylphenyl) -1-phenylethylene,
1- (3-N, N-diethylaminomethylphenyl) -1-phenylethylene,
1- (3-N, N-dipropylaminomethylphenyl) -1-phenylethylene,
1- (3-N, N-diisopropylaminomethylphenyl) -1-phenylethylene,
1- (3-N, N-dibutylaminomethylphenyl) -1-phenylethylene,
1- (3-N, N-diisobutylaminomethylphenyl) -1-phenylethylene,
1- (3-N, N-di (tert-butyl) aminomethylphenyl) -1-phenylethylene,
1- (3-N, N-diphenylaminomethylphenyl) -1-phenylethylene,
1- (3- (1-aziridinylmethyl) phenyl) -1-phenylethylene,
1- (3- (1-pyrrolidinylmethyl) phenyl) -1-phenylethylene,
1- (3- (1-piperidinylmethyl) phenyl) -1-phenylethylene,
1- (3-hexamethyleneiminomethylphenyl) -1-phenylethylene,
1- (3-morpholinomethylphenyl) -1-phenylethylene,
1- (3- (N, N-bis (trimethylsilyl) aminomethyl) phenyl) -1-phenylethylene,
1- (3- (N, N-bis (tert-butyldimethylsilyl) amino) methylphenyl) -1-phenylethylene,
1- (3- (N, N-bis (triisopropylsilyl) amino) methylphenyl) -1-phenylethylene.

As a compound represented by the formula (32), V ³⁰² is a group represented by the formula (32-V1), R ³²¹ in the formula (32-V1) is a hydrogen atom, and m ³ is 0. As examples of the compound wherein A ³⁰² is a nitrogen-containing aliphatic heterocyclic group, the following compounds can be given.

N-methyl-3-vinylpyrrolidine,
N-methyl-4-vinylpiperidine,
N-methyl-3-vinylhexamethyleneimine,
N-methyl-4-vinylhexamethyleneimine.

As a compound represented by the formula (32), V ³⁰² is a group represented by the formula (32-V1), R ³²¹ in the formula (32-V1) is a hydrogen atom, and m ³ is 1. In addition, examples of the compound in which R ³²² is a phenylene group and A ³⁰² is a nitrogen-containing aliphatic heterocyclic group include the following compounds.

N-methyl-3- (4-vinylphenyl) pyrrolidine,
N-methyl-4- (4-vinylphenyl) piperidine,
N-methyl-3- (4-vinylphenyl) hexamethyleneimine,
N-methyl-4- (4-vinylphenyl) hexamethyleneimine,
N-methyl-3- (3-vinylphenyl) pyrrolidine,
N-methyl-4- (3-vinylphenyl) piperidine,
N-methyl-3- (3-vinylphenyl) hexamethyleneimine,
N-methyl-4- (3-vinylphenyl) hexamethyleneimine.

As a compound represented by the formula (32), V ³⁰² is a group represented by the formula (32-V1), R ³²¹ in the formula (32-V1) is a hydrogen atom, and m ³ is 1. In addition, examples of the compound in which R ³²² is a group represented by the formula (32-Ra) and A ³⁰² is a nitrogen-containing aliphatic heterocyclic group include the following compounds.

A compound in which i ^{3 of} formula (32-Ra) is 1:
N-methyl-3- (4-vinylphenylmethyl) pyrrolidine,
N-methyl-4- (4-vinylphenylmethyl) piperidine,
N-methyl-3- (4-vinylphenylmethyl) hexamethyleneimine,
N-methyl-4- (4-vinylphenylmethyl) hexamethyleneimine.

A compound in which i ^{3 of} formula (32-Ra) is 2:
N-methyl-3- (4-vinylphenylethyl) pyrrolidine,
N-methyl-4- (4-vinylphenylethyl) piperidine,
N-methyl-3- (4-vinylphenylethyl) hexamethyleneimine,
N-methyl-4- (4-vinylphenylethyl) hexamethyleneimine.

As a compound represented by the formula (32), V ³⁰² is a group represented by the formula (32-V1), R ³²¹ in the formula (32-V1) is a hydrogen atom, and m ³ is 1. In addition, examples of the compound in which R ³²² is a group represented by the formula (32-Rb) and A ³⁰² is a nitrogen-containing aliphatic heterocyclic group include the following compounds.

A compound in which j ^{3 of} formula (32-Rb) is 1:
N-methyl-3- (3-vinylphenylmethyl) pyrrolidine,
N-methyl-4- (3-vinylphenylmethyl) piperidine,
N-methyl-3- (3-vinylphenylmethyl) hexamethyleneimine,
N-methyl-4- (3-vinylphenylmethyl) hexamethyleneimine.

A compound in which j ^{3 of} formula (32-Rb) is 2:
N-methyl-3- (3-vinylphenylethyl) pyrrolidine,
N-methyl-4- (3-vinylphenylethyl) piperidine,
N-methyl-3- (3-vinylphenylethyl) hexamethyleneimine,
N-methyl-4- (3-vinylphenylethyl) hexamethyleneimine.

As a compound represented by Formula (32), V ³⁰² is a group represented by Formula (32-V1), R ³²¹ in Formula (32-V1) is a methyl group, and m ³ is 0. As examples of the compound wherein A ³⁰² is a nitrogen-containing aliphatic heterocyclic group, the following compounds can be given.

N-methyl-3-isopropenylpyrrolidine,
N-methyl-4-isopropenylpiperidine,
N-methyl-3-isopropenylhexamethyleneimine,
N-methyl-4-isopropenylhexamethyleneimine.

As a compound represented by the formula (32), V ³⁰² is a group represented by the formula (32-V1), R ³²¹ in the formula (32-V1) is a methyl group, and m ³ is 1. In addition, examples of the compound in which R ³²² is a phenylene group and A ³⁰² is a nitrogen-containing aliphatic heterocyclic group include the following compounds.

N-methyl-3- (4-isopropenylphenyl) pyrrolidine,
N-methyl-4- (4-isopropenylphenyl) piperidine,
N-methyl-3- (4-isopropenylphenyl) hexamethyleneimine,
N-methyl-4- (4-isopropenylphenyl) hexamethyleneimine.

As a compound represented by the formula (32), V ³⁰² is a group represented by the formula (32-V1), R ³²¹ in the formula (32-V1) is a methyl group, and m ³ is 1. In addition, examples of the compound in which R ³²² is a group represented by the formula (32-Ra) and A ³⁰² is a nitrogen-containing aliphatic heterocyclic group include the following compounds.

A compound in which i ^{3 of} formula (32-Ra) is 1:
N-methyl-3- (4-isopropenylphenylmethyl) pyrrolidine,
N-methyl-4- (4-isopropenylphenylmethyl) piperidine,
N-methyl-3- (4-isopropenylphenylmethyl) hexamethyleneimine,
N-methyl-4- (4-isopropenylphenylmethyl) hexamethyleneimine.

A compound in which i ^{3 of} formula (32-Ra) is 2:
N-methyl-3- (4-isopropenylphenylethyl) pyrrolidine,
N-methyl-4- (4-isopropenylphenylethyl) piperidine,
N-methyl-3- (4-isopropenylphenylethyl) hexamethyleneimine,
N-methyl-4- (4-isopropenylphenylethyl) hexamethyleneimine.

As a compound represented by Formula (32), V ³⁰² is a group represented by Formula (32-V1), R ³²¹ in Formula (32-V1) is a vinyl group, and m ³ is 0. As examples of the compound wherein A ³⁰² is a nitrogen-containing aliphatic heterocyclic group, the following compounds can be given.

N-methyl-3- (1-methylene-2-propenyl) pyrrolidine,
N-methyl-4- (1-methylene-2-propenyl) piperidine,
N-methyl-3- (1-methylene-2-propenyl) hexamethyleneimine,
N-methyl-4- (1-methylene-2-propenyl) hexamethyleneimine.

As a compound represented by Formula (32), V ³⁰² is a group represented by Formula (32-V1), R ³²¹ in Formula (32-V1) is a vinyl group, and m ³ is 1. Yes, examples of the compound in which R ³²² is an alkylene group and A ³⁰² is a nitrogen-containing aliphatic heterocyclic group include the following compounds.

Compound wherein R ³²² is a methylene group:
N-methyl-3- (2-methylene-3-butenyl) pyrrolidine,
N-methyl-4- (2-methylene-3-butenyl) piperidine,
N-methyl-3- (2-methylene-3-butenyl) hexamethyleneimine,
N-methyl-4- (2-methylene-3-butenyl) hexamethyleneimine.

A compound in which R ³²² is an ethylene group:
N-methyl-3- (3-methylene-4-pentenyl) pyrrolidine,
N-methyl-4- (3-methylene-4-pentenyl) piperidine,
N-methyl-3- (3-methylene-4-pentenyl) hexamethyleneimine,
N-methyl-4- (3-methylene-4-pentenyl) hexamethyleneimine.

As a compound represented by the formula (32), V ³⁰² is a group represented by the formula (32-V1), R ³²¹ in the formula (32-V1) is a phenyl group, and m ³ is 1. In addition, examples of the compound in which R ³²² is a phenylene group and A ³⁰² is a nitrogen-containing aliphatic heterocyclic group include the following compounds.

1- (4-N-methyl-3-pyrrolidinophenyl) -1-phenylethylene,
1- (4-N-methyl-3-piperidinophenyl) -1-phenylethylene,
1- (4-N-methyl-4-piperidinophenyl) -1-phenylethylene,
1- (4-N-methyl-3-hexamethyleneiminophenyl) -1-phenylethylene,
1- (4-N-methyl-4-hexamethyleneiminophenyl) -1-phenylethylene,
1- (3-N-methyl-3-pyrrolidinophenyl) -1-phenylethylene,
1- (3-N-methyl-3-piperidinophenyl) -1-phenylethylene,
1- (3-N-methyl-4-piperidinophenyl) -1-phenylethylene,
1- (3-N-methyl-3-hexamethyleneiminophenyl) -1-phenylethylene,
1- (3-N-methyl-4-hexamethyleneiminophenyl) -1-phenylethylene.

As a compound represented by the formula (32), V ³⁰² is a group represented by the formula (32-V1), R ³²¹ in the formula (32-V1) is a phenyl group, and m ³ is 1. In addition, examples of the compound in which R ³²² is a group represented by the formula (32-Ra) and A ³⁰² is a nitrogen-containing aliphatic heterocyclic group include the following compounds.

A compound in which i ^{3 of} formula (32-Ra) is 1:
1- (4-N-methyl-3-pyrrolidinomethylphenyl) -1-phenylethylene,
1- (4-N-methyl-3-piperidinomethylphenyl) -1-phenylethylene,
1- (4-N-methyl-4-piperidinomethylphenyl) -1-phenylethylene,
1- (4-N-methyl-3-hexamethyleneiminomethylphenyl) -1-phenylethylene.

As a compound represented by the formula (32), V ³⁰² is a group represented by the formula (32-V1), R ³²¹ in the formula (32-V1) is a phenyl group, and m ³ is 1. In addition, examples of the compound in which R ³²² is a group represented by the formula (32-Rb) and A ³⁰² is a nitrogen-containing aliphatic heterocyclic group include the following compounds.

A compound in which j ^{3 of} formula (32-Rb) is 1:
1- (3-N, N-dimethylaminomethylphenyl) -1-phenylethylene,
1- (3-N, N-diethylaminomethylphenyl) -1-phenylethylene,
1- (3-N, N-dipropylaminomethylphenyl) -1-phenylethylene,
1- (3-N, N-diisopropylaminomethylphenyl) -1-phenylethylene.

As a compound represented by the formula (32), V ³⁰² is a group represented by the formula (32-V1), R ³²¹ in the formula (32-V1) is a hydrogen atom, and m ³ is 0. As examples of the compound in which A ³⁰² is a nitrogen-containing aromatic heterocyclic group, the following compounds can be given.

N-methyl-2-vinylimidazole,
N-methyl-4-vinylimidazole,
N-methyl-5-vinylimidazole,
2-vinylpyridine,
3-vinylpyridine,
4-vinylpyridine,
2-vinylquinoline,
3-vinyl quinoline,
4-Vinylquinoline.

As a compound represented by Formula (32), V ³⁰² is a group represented by Formula (32-V1), R ³²¹ in Formula (32-V1) is a methyl group, and m ³ is 0. As examples of the compound in which A ³⁰² is a nitrogen-containing aromatic heterocyclic group, the following compounds can be given.

N-methyl-2-isopropenylimidazole,
N-methyl-4-isopropenylimidazole,
N-methyl-5-isopropenylimidazole,
2-isopropenyl pyridine,
3-isopropenyl pyridine,
4-isopropenyl pyridine,
2-isopropenyl quinoline,
3-isopropenyl quinoline,
4-Isopropenylquinoline.

As a compound represented by Formula (32), V ³⁰² is a group represented by Formula (32-V1), R ³²¹ in Formula (32-V1) is a vinyl group, and m ³ is 0. As examples of the compound in which A ³⁰² is a nitrogen-containing aromatic heterocyclic group, the following compounds can be given.

N-methyl-2- (1-methylene-2-propenyl) imidazole,
N-methyl-4- (1-methylene-2-propenyl) imidazole,
N-methyl-5- (1-methylene-2-propenyl) imidazole,
2- (1-methylene-2-propenyl) pyridine,
3- (1-methylene-2-propenyl) pyridine,
4- (1-methylene-2-propenyl) pyridine,
2- (1-methylene-2-propenyl) quinoline,
3- (1-methylene-2-propenyl) quinoline,
4- (1-methylene-2-propenyl) quinoline.

As a compound represented by the formula (32), V ³⁰² is a group represented by the formula (32-V1), R ³²¹ in the formula (32-V1) is a vinyl group, and m ³ is 1. As examples of the compound in which R ³²² is an alkylene group and A ³⁰² is a nitrogen-containing aromatic heterocyclic group, the following compounds can be given.

Compound wherein R ³²² is a methylene group:
N-methyl-2- (2-methylene-3-butenyl) imidazole,
N-methyl-4- (2-methylene-3-butenyl) imidazole,
N-methyl-5- (2-methylene-3-butenyl) imidazole,
2- (2-methylene-3-butenyl) pyridine,
3- (2-methylene-3-butenyl) pyridine,
4- (2-methylene-3-butenyl) pyridine,
2- (2-methylene-3-butenyl) quinoline,
3- (2-methylene-3-butenyl) quinoline,
4- (2-Methylene-3-butenyl) quinoline.

A compound in which R ³²² is an ethylene group:
N-methyl-2- (3-methylene-4-pentenyl) imidazole,
N-methyl-4- (3-methylene-4-pentenyl) imidazole,
N-methyl-5- (3-methylene-4-pentenyl) imidazole,
2- (3-methylene-4-pentenyl) pyridine,
3- (3-methylene-4-pentenyl) pyridine,
4- (3-methylene-4-pentenyl) pyridine,
2- (3-methylene-4-pentenyl) quinoline,
3- (3-methylene-4-pentenyl) quinoline,
4- (3-Methylene-4-pentenyl) quinoline.

The compound represented by the formula (32) is preferably a compound in which the group represented by V ³⁰² is represented by the formula (32-V1), and R ³²¹ in the formula (32-V1) is a hydrogen atom. is there.
More preferably, R ³²¹ is a hydrogen atom, m ³ is 1, R ³²² is a group represented by the formula (32-Ra), and A ³⁰² is a substituted amino group.
More preferably, R ³²¹ is a hydrogen atom, m ³ is 1, R ³²² is a group represented by the formula (32-Ra), and i ^{3 in the} formula (32-Ra) is 1. A ³⁰² is a compound in which a substituted amino group is present.

The compound represented by the formula (32) is particularly preferably
4-N, N-dimethylaminomethylstyrene,
4-N, N-bis (trimethylsilyl) aminostyrene,
4-N, N-bis (trimethylsilyl) aminomethylstyrene,
It is.

（式中、Ｅは、酸素原子又は硫黄原子を表し、Ｚ^３０１及びＺ^３０２は、置換アミノ基、水素原子、置換基を有していてもよいヒドロカルビル基、又は、置換基を有していてもよいヒドロカルビルオキシ基を表し、Ｚ^３０１及びＺ^３０２の少なくとも１つが置換アミノ基を有する基であるか、あるいは、Ｚ^３０１とＺ^３０２とが結合して、置換アミノ基を有する環構造をＺ^３０１とＺ^３０２とカルボニル炭素とで形成する基を表す。） As the compound (G), a compound represented by the following formula (33) can be exemplified.

(In the formula, E represents an oxygen atom or a sulfur atom, and Z ³⁰¹ and Z ³⁰² have a substituted amino group, a hydrogen atom, a hydrocarbyl group which may have a substituent, or a substituent. represents also good hydrocarbyloxy ^group, or a group having at least one substituted amino group of ^{Z 301} and ^{Z 302, or} by bonding with ^{Z 301} and ^{Z 302,} a ring structure having a substituted amino group ^{Z 301} And represents a group formed by Z ³⁰² and a carbonyl carbon.)

In formula (33), E represents an oxygen atom or a sulfur atom. Preferably, it is an oxygen atom.

In formula (33), the substituted amino group of Z ³⁰¹ and Z ³⁰² is substituted with an amino group having a hydrocarbyl group as a substituent, an amino group having a group having a substituted amino group as a substituent, or a group having a hydrocarbyloxy group Examples thereof include an amino group as a group.

Examples of the amino group having a hydrocarbyl group as a substituent include dialkylamino groups such as a dimethylamino group, a diethylamino group, and a dipropylamino group.

Examples of the amino group having a substituted amino group as a substituent include (dimethylaminomethyl) amino group, (dimethylaminoethyl) amino group, (dimethylaminopropyl) amino group, (diethylaminopropyl) amino group, (dipropyl) (Dialkylaminoalkyl) amino groups such as aminopropyl) amino group; bis (dialkylaminoalkyl) amino groups such as bis (dimethylaminoethyl) amino group and bis (dimethylaminopropyl) amino group.

The amino group having a hydrocarbyloxy group-containing group as a substituent includes (alkoxyalkyl) amino such as (methoxymethyl) amino group, (methoxyethyl) amino group, (methoxypropyl) amino group, and (ethoxymethyl) amino group. (Aryloxyalkyl) amino groups such as (phenoxymethyl) amino group and (phenoxyethyl) amino group; (aralkyloxyalkyl) amino groups such as (benzyloxymethyl) amino group and (benzyloxyethyl) amino group can give.

Examples of the hydrocarbyl group optionally having a substituent of Z ³⁰¹ and Z ³⁰² include a hydrocarbyl group, a hydrocarbyl group having a substituted amino group as a substituent, and a hydrocarbyl group having a hydrocarbyloxy group as a substituent.

Examples of the hydrocarbyl group include alkyl groups such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, and an n-butyl group; a cycloalkyl group such as a cyclohexyl group; an aryl group such as a phenyl group, a methylphenyl group, and an ethylphenyl group An aralkyl group such as a benzyl group; an alkenyl group such as a vinyl group, a 1-propenyl group, an allyl group, an isopropenyl group, a crotyl group, an isocrotyl group, and a methallyl group; and an alkynyl group such as a propargyl group.

Examples of the hydrocarbyl group having a substituted amino group as a substituent include a hydrocarbyl group having a hydrocarbyl-substituted amino group as a substituent. Examples of the hydrocarbyl group having a hydrocarbyl-substituted amino group as a substituent include dialkylaminoalkyl groups such as dimethylaminomethyl group, dimethylaminoethyl group, and dimethylaminopropyl group; dialkylaminoaryl groups such as dimethylaminophenyl group and diethylaminophenyl group. can give.

Examples of the hydrocarbyl group having a hydrocarbyloxy group as a substituent include alkoxyalkyl groups such as methoxymethyl group, methoxyethyl group, methoxypropyl group, and ethoxymethyl group; aryloxyalkyl groups such as phenoxymethyl group and phenoxyethyl group; benzyloxy And aralkyloxyalkyl groups such as a methyl group and a benzyloxyethyl group.

Examples of the hydrocarbyloxy group optionally having a substituent of Z ³⁰¹ and Z ³⁰² include a hydrocarbyloxy group, a hydrocarbyloxy group having a hydrocarbyloxy group as a substituent, and a hydrocarbyloxy group having a substituted amino group as a substituent. It is done.

Hydrocarbyloxy groups include alkoxy groups such as methoxy, ethoxy, n-propoxy, isopropoxy and butoxy; aryloxy groups such as phenoxy, methylphenoxy and ethylphenoxy; aralkyl such as benzyloxy An oxy group etc. are mention | raise | lifted.

Examples of the hydrocarbyloxy group having a hydrocarbyloxy group as a substituent include an alkoxyalkoxy group such as a methoxymethoxy group, a methoxyethoxy group, a methoxypropoxy group, and an ethoxymethoxy group; an aryloxyalkoxy group such as a phenoxymethoxy group and a phenoxyethoxy group; Examples thereof include aralkyloxyalkoxy groups such as oxymethoxy group and benzyloxyethoxy group.

Examples of the hydrocarbyloxy group having a substituted amino group as a substituent include a hydrocarbyloxy group having a hydrocarbyl-substituted amino group as a substituent. Examples of the hydrocarbyloxy group having a hydrocarbyl-substituted amino group as a substituent include dialkylaminoalkoxy groups such as a dimethylaminomethoxy group, a dimethylaminoethoxy group, and a dimethylaminopropoxy group.

（式中、ｐ^３は０又は１であり、Ｔ^３０１は炭素原子数１〜１０のヒドロカルビレン基、下記式（３３−Ｔａ）で表される基、又は、下記式（３３−Ｔｂ）で表される基を表し、Ａ^３０３は置換アミノ基を表す。）

（式中、Ｒ^３３１は炭素原子数１〜１０のヒドロカルビレン基を表し、Ｒ^３３１がＡ^３０３と結合する。）

（式中、Ｒ^３３２は炭素原子数１〜１０のヒドロカルビレン基を表し、Ｒ^３３３は水素原子又は炭素原子数１〜１０のヒドロカルビル基を表し、Ｒ^３３２がＡ^３０３と結合する。） The group having a substituted amino group is preferably a group represented by the following formula (33-Z).

(In the formula, p ³ is 0 or 1, and T ³⁰¹ is a hydrocarbylene group having 1 to 10 carbon atoms, a group represented by the following formula (33-Ta), or a following formula (33-Tb). And A ³⁰³ represents a substituted amino group.)

^{(Wherein, R 331} represents a hydrocarbylene group having 1 to 10 carbon ^{atoms, R 331} is bonded to ^{A 303.)}

(Wherein R ³³² represents a hydrocarbylene group having 1 to 10 carbon atoms, R ³³³ represents a hydrogen atom or a hydrocarbyl group having 1 to 10 carbon atoms, and R ³³² is bonded to A ^303. )

When Z ³⁰¹ in formula (33) is a group represented by formula (33-Z) and Z ³⁰² is a hydrocarbyl group, A ³⁰³ in Z ³⁰¹ and the hydrocarbyl group in Z ³⁰² may be bonded to each other. . Also, if ^{Z 301} and ^{Z 302} of formula (33) is a group represented by the formula ^(33-Z), it may be bonded to the ^{A 303} of the ^{A 303} and ^{Z 302} for ^{Z 301.}

In Formula (33-Z), p ³ represents 0 or 1.

In Formula (33-Z), T ³⁰¹ represents a hydrocarbylene group having 1 to 10 carbon atoms, a group represented by Formula (33-Ta), or a group represented by Formula (33-Tb). Represent.

Examples of the hydrocarbylene group having 1 to 10 carbon atoms of T ³⁰¹ include alkylene groups such as methylene group, ethylene group, trimethylene group, tetramethylene group, pentamethylene group, hexamethylene group; and arylene groups such as phenylene group and naphthylene group Group.

In formula (33-Ta), R ³³¹ represents a hydrocarbylene group having 1 to 10 carbon atoms, and in formula (33-Tb), R ³³² represents a hydrocarbylene group having 1 to 10 carbon atoms, R ³³³ represents a hydrogen atom or a hydrocarbyl group having 1 to 10 carbon atoms.

Examples of the hydrocarbylene group having 1 to 10 carbon atoms of R ³³¹ and R ³³² include alkylene groups such as methylene group, ethylene group, trimethylene group, tetramethylene group, pentamethylene group, hexamethylene group; phenylene group, naphthylene group An arylene group such as Preferably, they are an ethylene group and a trimethylene group.

Examples of the hydrocarbyl group having 1 to 10 carbon atoms of R ³³³ include an alkyl group, an aralkyl group, and an aryl group. Examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, and tert-butyl group. Examples of the aralkyl group include a benzyl group. A phenyl group etc. can be mention | raise | lifted as an aryl group. An alkyl group having 1 to 10 carbon atoms is preferable, and a methyl group or an ethyl group is more preferable. R ³³³ is preferably a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and more preferably a hydrogen atom, a methyl group, or an ethyl group.

Examples of the group represented by the formula (33-Ta) include a group represented by —O—CH ₂ CH ₂ — and a group represented by —O—CH ₂ CH ₂ CH ₂ —.

Examples of the group represented by the formula (33-Tb) include a group represented by —NH—CH ₂ CH ₂ — and a group represented by —NH—CH ₂ CH ₂ CH ₂ —.

（式中、Ｒ^３３４及びＲ^３３５は、それぞれ、窒素原子及び／又は酸素原子を有していてもよいヒドロカルビル基、又は、トリヒドロカルビルシリル基、あるいは、Ｒ^３３４とＲ^３３５とが結合して、窒素原子及び／又は酸素原子をヘテロ原子として有していてもよいヒドロカルビレン基、又は、Ｒ^３３４とＲ^３３５は１つの基であって、窒素原子に二重結合で結合する基を表す。） The group represented by A ³⁰³ in formula (33-Z) is preferably a group represented by the following formula (33-A).

(In the formula, R ³³⁴ and R ³³⁵ are each a hydrocarbyl group or a trihydrocarbylsilyl group optionally having a nitrogen atom and / or an oxygen atom, or R ³³⁴ and R ³³⁵ are bonded, A hydrocarbylene group which may have a nitrogen atom and / or an oxygen atom as a hetero atom, or R ³³⁴ and R ³³⁵ are one group and represent a group bonded to the nitrogen atom with a double bond. )

^Examples of the hydrocarbyl group of R ³³⁴ and R ³³⁵ include an alkyl group, an alkenyl group, an alkynyl group, an aryl group, and an aralkyl group. Examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, and tert-butyl group. Examples of the alkenyl group include a vinyl group, an allyl group, a 1-propenyl group, and a 1-methylethenyl group. Examples of the alkynyl group include an ethynyl group and a propargyl group. Examples of the aryl group include a phenyl group, a tolyl group, and a xylyl group. Examples of the aralkyl group include a benzyl group.

The number of carbon atoms of the hydrocarbyl group of R ³³⁴ and R ³³⁵ is preferably 1 to 10, more preferably 1 to 4, and still more preferably 1 to 2.

The hydrocarbyl group of R ³³⁴ and R ³³⁵ is preferably an alkyl group or an alkenyl group, more preferably an alkyl group, and still more preferably a linear alkyl group.

^Examples of the hydrocarbyl group having a nitrogen atom of R ³³⁴ and R ³³⁵ include dialkylaminoalkyl groups such as a dimethylaminomethyl group, a dimethylaminoethyl group, a dimethylaminopropyl group, and a diethylaminoethyl group. The number of carbon atoms of the hydrocarbyl group having a nitrogen atom of R ³³⁴ and R ³³⁵ is preferably 3 to 10, more preferably 3 to 6, and further preferably 3 to 4.

^Examples of the hydrocarbyl group having an oxygen atom of R ³³⁴ and R ³³⁵ include an alkoxyalkyl group such as a methoxymethyl group, a methoxyethyl group, a methoxypropyl group, an ethoxymethyl group, and an ethoxyethyl group; an oxacyclo group such as an oxiranyl group and a tetrahydrofuranyl group. An alkyl group; an oxacycloalkylalkyl group such as a glycidyl group and a tetrahydrofurfuryl group. The number of carbon atoms of the hydrocarbyl group having an oxygen atom of R ³³⁴ and R ³³⁵ is preferably 2 to 10, more preferably 2 to 6, and further preferably 2 to 4.

In this specification, the oxacycloalkyl group represents a group in which CH ₂ on the alicyclic ring of the cycloalkyl group is replaced with an oxygen atom, and the oxacycloalkylalkyl group is a group in which a hydrogen atom of the alkyl group is replaced with an oxacycloalkyl group. Represents a group.

The trihydrocarbyl silyl group R ³³⁴ and R ^335, may be mentioned trimethylsilyl group, triethylsilyl group, triisopropylsilyl group, a trialkylsilyl group such as tert- butyldimethylsilyl group.

The trihydrocarbylsilyl group of R ³³⁴ and R ³³⁵ is preferably a trialkylsilyl group having 3 to 9 carbon atoms, more preferably an alkyl group bonded to a silicon atom having 1 to 4 carbon atoms. A trialkylsilyl group which is an alkyl group, and more preferably a trimethylsilyl group.

The hydrocarbylene group optionally having a nitrogen atom and / or an oxygen atom to which R ³³⁴ and R ³³⁵ are bonded as a hetero atom includes a hydrocarbylene group, a hydrocarbylene group having a nitrogen atom, and an oxygen atom. And hydrocarbylene groups. Examples of the hydrocarbylene group include an alkylene group such as an ethylene group, a trimethylene group, a tetramethylene group, a pentamethylene group, and a hexamethylene group. As the hydrocarbylene group having a nitrogen atom, a group represented by —CH ₂ CH ₂ —NH—CH ₂ —, a group represented by —CH ₂ CH ₂ —N═CH—, —CH═CH—N A group represented by ═CH— and a group represented by —CH ₂ CH ₂ —NH—CH ₂ CH ₂ — can be exemplified. Examples of the hydrocarbylene group having an oxygen atom include a group represented by —CH ₂ CH ₂ —O—CH ₂ CH ₂ —.

The number of carbon atoms of the group to which R ³³⁴ and R ³³⁵ are bonded is preferably 2 to 20, more preferably 2 to 7, and still more preferably 4 to 6.

The hydrocarbylene group which may have a nitrogen atom and / or oxygen atom to which R ³³⁴ and R ³³⁵ are bonded as a hetero atom is preferably a hydrocarbylene group, more preferably an alkylene group, A polymethylene group is preferred.

Examples of one group in which R ³³⁴ and R ³³⁵ are bonded to the nitrogen atom by a double bond include ethylidene group, propylidene group, butylidene group, 1-methylethylidene group, 1-methylpropylidene group, 1,3-dimethylbutylidene And hydrocarbylidene groups such as groups.

The number of carbon atoms of one group in which R ³³⁴ and R ³³⁵ are bonded to the nitrogen atom with a double bond is preferably 2 to 20, and more preferably 2 to 6.

R ³³⁴ and R ³³⁵ are preferably a hydrocarbyl group, a trihydrocarbyl silyl group, or a hydrocarbylene group in which R ³³⁴ and R ³³⁵ are bonded.

Examples of the group represented by the formula (33-A) include an acyclic amino group and a cyclic amino group.

Examples of the acyclic amino group include a dialkylamino group and a bis (trialkylsilyl) amino group. Dialkylamino groups include dimethylamino, diethylamino, di (n-propyl) amino, di (isopropyl) amino, di (n-butyl) amino, di (sec-butyl) amino, di (tert -Butyl) amino group and ethylmethylamino group can be mentioned. Examples of the bis (trialkylsilyl) amino group include a bis (trimethylsilyl) amino group and a bis (tert-butyldimethylsilyl) amino group.

The acyclic amino group further includes an ethylideneamino group, a 1-methylpropylideneamino group, a 1,3-dimethylbutylideneamino group, a 1-methylethylideneamino group, and a 4-N, N-dimethylaminobenzylideneamino group. You can also give it.

Examples of the cyclic amino group include 1-aziridinyl group, 1-azetidinyl group, 1-pyrrolidinyl group, 1-piperidinyl group, 1-hexamethyleneimino group, 1-imidazolyl group, 4,5-dihydro-1-imidazolyl group, 1 Examples include -pyrrolyl group, 1-pyrazolyl group, 1-imidazolidinyl group, 1-piperazinyl group, and morpholino group.

The group represented by the formula (33-A) is preferably a group in which R ³³⁴ and R ³³⁵ are hydrocarbyl groups, a group in which R ³³⁴ and R ³³⁵ are trihydrocarbyl silyl groups, and R ³³⁴ and R ³³⁵ are oxa groups. A group that is a cycloalkylalkyl group, and a group that is a hydrocarbylene group to which R ³³⁴ and R ³³⁵ are bonded. More preferably, R ³³⁴ and R ³³⁵ are groups that are linear alkyl groups, R ³³⁴ and R ³³⁵ are groups that are trialkylsilyl groups, and R ³³⁴ and R ³³⁵ are groups that are polymethylene groups bonded to each other.

The group represented by formula (33-A) is more preferably a dialkylamino group.

Examples of the group represented by the formula (33-Z) in which p ³ = 0 include dihydrocarbylamino groups such as dimethylamino group and diethylamino group; 1-aziridinyl group, 1-pyrrolidinyl group, 1-piperidinyl group, 1- Cyclic amino groups such as hexamethyleneimino, 1-imidazolyl, 4,5-dihydro-1-imidazolyl, 1-imidazolidinyl, 1-piperazinyl, morpholino; di (glycidyl) amino, di (tetrahydrofur Di (oxacycloalkylalkyl) amino group such as furyl) amino group; bis (trimethylsilyl) amino group, bis (triethylsilyl) amino group, bis (t-butyldimethylsilyl) amino group, bis (triisopropylsilyl) amino group And bis (trialkylsilyl) amino group.

Examples of the group represented by the formula (33-Z) in which p ³ = 1 and T ³⁰¹ is a hydrocarbylene group include dihydrocarbylamino such as dimethylaminoethyl group, diethylaminoethyl group, dimethylaminopropyl group, and diethylaminopropyl group. An alkyl group; a dihydrocarbylaminoaryl group such as a dimethylaminophenyl group and a diethylaminophenyl group.

The group represented by the formula (33-Z) in which p ³ = 1 and T ³⁰¹ is a group represented by the formula (33-Ta) is —O—CH ₂ CH ₂ —N (CH ₃ ) ₂ . a group represented _{by, -O-CH 2 CH 2 -N} (CH 2 CH 3) 2 _, a group represented by _the group represented by _{-O-CH 2 CH 2 CH 2} -N (CH 3) 2, - A group represented by O—CH ₂ CH ₂ CH ₂ —N (CH ₂ CH ₃ ) ₂ can be given.

The group represented by the formula (33-Z) in which p ³ = 1 and T ³⁰¹ is a group represented by the formula (33-Tb) is —NH—CH ₂ CH ₂ —N (CH ₃ ) ₂ a group represented _{by, -NH-CH 2 CH 2 -N} (CH 2 CH 3) 2 _, a group represented by _the group represented by _{-NH-CH 2 CH 2 CH 2} -N (CH 3) 2 -NH A group represented by —CH ₂ CH ₂ CH ₂ —N (CH ₂ CH ₃ ) ₂ can be given.

Examples of the compound represented by the formula (33) include a carboxylic acid amide compound, a thiocarboxylic acid amide compound, a carboxylic acid ester compound, and a thiocarboxylic acid ester compound.

As a carboxylic acid amide compound,
Formamide compounds such as N, N-dimethylformamide, N, N-diethylformamide;
N, N-dimethylacetamide, N, N-diethylacetamide, aminoacetamide, N, N-dimethyl-N ′, N′-dimethylaminoacetamide, N, N-dimethylaminoacetamide, N, N-dimethyl-N′- Acetamide compounds such as ethylaminoacetamide, N, N-dimethylaminoacetamide, N-phenyldiacetamide;
Propionamide compounds such as N, N-dimethylpropionamide;
N, N-dimethylbenzamide, N ′, N ′-(p-dimethylamino) benzamide, N ′, N ′-(p-diethylamino) benzamide, N, N-dimethyl-N ′, N ′-(p-dimethyl) Benzamide compounds such as amino) benzamide, N, N-dimethyl-N ′, N ′-(p-diethylamino) benzamide;
Pyridylamide compounds such as N, N-dimethyl-4-pyridylamide;
Examples thereof include phthalamide compounds such as N, N, N ′, N′-tetramethylphthalamide and N, N, N ′, N′-tetraethylphthalamide.

As the thiocarboxylic acid amide compound,
Thioformamide compounds such as N, N-dimethylthioformamide, N, N-diethylthioformamide;
N, N-dimethylthioacetamide, N, N-diethylthioacetamide, aminothioacetamide, N, N-dimethyl-N ′, N′-dimethylaminothioacetamide, N, N-dimethylaminothioacetamide, N, N— Thioacetamide compounds such as dimethyl-N′-ethylaminothioacetamide, N, N-dimethylaminothioacetamide, N-phenyldithioacetamide;
Thiopropionamide compounds such as N, N-dimethylthiopropionamide;
N, N-dimethylthiobenzamide, N ′, N ′-(p-dimethylamino) thiobenzamide, N ′, N ′-(p-diethylamino) thiobenzamide, N, N-dimethyl-N ′, N ′-( thiobenzamide compounds such as p-dimethylaminothiobenzamide, N, N-dimethyl-N ′, N ′-(p-diethylamino) thiobenzamide;
Pyridylthioamide compounds such as N, N-dimethyl-4-pyridylthioamide;
Examples thereof include thiophthalamide compounds such as N, N, N ′, N′-tetramethylthiophthalamide and N, N, N ′, N′-tetraethylthiophthalamide.

As the carboxylic acid ester compound,
N, N-dialkylaminomethyl acetate such as N, N-dimethylaminomethyl acetate, N, N-diethylaminomethyl acetate;
N, N-dialkylaminoethyl acetate such as N, N-dimethylaminoethyl acetate, N, N-diethylaminoethyl acetate;
N, N-dialkylaminopropyl acetate such as N, N-dimethylaminopropyl acetate, N, N-diethylaminopropyl acetate;
N, N-dialkylaminoethyl benzoate such as N, N-dimethylaminoethyl benzoate and N, N-diethylaminoethyl benzoate can be used.

As the thiocarboxylic acid ester compound,
N, N-dialkylaminomethylthioacetate such as N, N-dimethylaminomethylthioacetate, N, N-diethylaminomethylthioacetate;
N, N-dialkylaminoethyl thioacetate such as N, N-dimethylaminoethyl thioacetate, N, N-diethylaminoethyl thioacetate;
N, N-dialkylaminopropylthioacetate such as N, N-dimethylaminopropylthioacetate, N, N-diethylaminopropylthioacetate;
N, N-dialkylaminoethylthiobenzoate such as N, N-dimethylaminoethylthiobenzoate, N, N-diethylaminoethylthiobenzoate and the like can be mentioned.

（式中、Ｅは、酸素原子、又は、硫黄原子を表し、Ｒ^３３４Ｒ^３３５Ｎ−はベンゼン環上の置換基であり、Ｒ^３３４及びＲ^３３５は、それぞれ、窒素原子及び／又は酸素原子を有していてもよいヒドロカルビル基、又は、トリヒドロカルビルシリル基、あるいは、Ｒ^３３４とＲ^３３５とが結合して、窒素原子及び／又は酸素原子をヘテロ原子として有していてもよいヒドロカルビレン基、又は、Ｒ^３３４とＲ^３３５は１つの基であって、窒素原子に二重結合で結合する基を表し、Ｒ^３３６は、ヒドロカルビル基、又は、水素原子を表す。）

（式中、Ｅは、酸素原子、又は、硫黄原子を表し、ｒ^３は０〜２の整数を表し、Ｒ^３３４Ｒ^３３５Ｎ−はベンゼン環上の置換基であり、Ｒ^３３４及びＲ^３３５は、それぞれ、窒素原子及び／又は酸素原子を有していてもよいヒドロカルビル基、又は、トリヒドロカルビルシリル基、あるいは、Ｒ^３３４とＲ^３３５とが結合して、窒素原子及び／又は酸素原子をヘテロ原子として有していてもよいヒドロカルビレン基、又は、Ｒ^３３４とＲ^３３５は１つの基であって、窒素原子に二重結合で結合する基を表す。） As a preferable compound represented by the formula (33), a compound in which Z ³⁰¹ is a group represented by the formula (33-Z) and Z ³⁰² is a hydrocarbyl group or a hydrogen atom which may have a substituent. Is given.
Examples of the compound include a compound represented by the following formula (33-1) in which p ³ in the formula (33-Z) is 1 and T ³⁰¹ is a phenylene group, and a compound represented by the following formula (33-2). Compounds.

(In the formula, E represents an oxygen atom or a sulfur atom, R ³³⁴ R ³³⁵ N- represents a substituent on the benzene ring, and R ³³⁴ and R ³³⁵ represent a nitrogen atom and / or an oxygen atom, respectively. Hydrocarbyl group which may have, or trihydrocarbylsilyl group, or hydrocarbylene group which R ³³⁴ and R ³³⁵ may combine to have a nitrogen atom and / or an oxygen atom as a hetero atom Or R ³³⁴ and R ³³⁵ are one group and represent a group bonded to a nitrogen atom by a double bond, and R ³³⁶ represents a hydrocarbyl group or a hydrogen atom.)

(In the formula, E represents an oxygen atom or a sulfur atom, r ³ represents an integer of 0 to 2, R ³³⁴ R ³³⁵ N- is a substituent on the benzene ring, and R ³³⁴ and R ³³⁵ are , A hydrocarbyl group which may have a nitrogen atom and / or an oxygen atom, or a trihydrocarbylsilyl group, or R ³³⁴ and R ³³⁵ are bonded to form a hetero atom for the nitrogen atom and / or the oxygen atom. Or R ³³⁴ and R ³³⁵ are one group and represent a group bonded to a nitrogen atom with a double bond.

E in Formula (33-1) and Formula (33-2) represents an oxygen atom or a sulfur atom, and preferably an oxygen atom.

R ^{3 in} formula (33-2) represents an integer of 0 to 2.

R ³³⁴ R ³³⁵ N- in formula (33-1) and formula (33-2) is a substituent on the benzene ring. R ³³⁴ and ^the definition of ^{R 335,} exemplary and preferred groups, ^{R 334} of formula (33-A), and ^the definitions described in ^{R 335,} is the same as the illustrative and preferred groups.

R ³³⁴ R ³³⁵ N— in formula (33-1) and formula (33-2) is preferably a dialkylamino group. The alkyl group of the dialkylamino group is preferably an alkyl group having 1 to 4 carbon atoms.

R ^{336 in} formula (33-1) represents a hydrogen atom or a hydrocarbyl group. Examples of the hydrocarbyl group include methyl groups, ethyl groups, n-propyl groups, isopropyl groups, n-butyl groups, sec-butyl groups, tert-butyl groups and other alkyl groups; phenyl groups, methylphenyl groups, ethylphenyl groups, and the like. An aralkyl group such as a benzyl group.

As a compound represented by Formula (33-1),
Dialkylamino-substituted benzaldehyde compounds such as 4-dimethylaminobenzaldehyde and 4-diethylaminobenzaldehyde;
Dialkylamino-substituted acetophenone compounds such as 4-dimethylaminoacetophenone and 4-diethylaminoacetophenone;
Heterocyclic group-substituted acetophenone compounds such as 4′-imidazol-1-yl-acetophenone, 4 ′-(1-pyrazolyl) acetophenone, 4-morpholinoacetophenone;
Dialkylamino-substituted thiobenzaldehyde compounds such as 4-dimethylaminothiobenzaldehyde and 4-diethylaminothiobenzaldehyde;
Dialkylamino-substituted thioacetophenone compounds such as 4-dimethylaminothioacetophenone and 4-diethylaminothioacetophenone;
Examples include heterocyclic group-substituted thioacetophenone compounds such as 4′-imidazol-1-yl-thioacetophenone, 4 ′-(1-pyrazolyl) thioacetophenone, 4-morpholinothioacetophenone.

As a compound represented by Formula (33-2),
Dialkylamino such as 3-dimethylaminobenzophenone, 3-diethylaminobenzophenone, 4-dimethylaminobenzophenone, 4-diethylaminobenzophenone, 4,4′-bis (dimethylamino) -benzophenone, 4,4′-bis (diethylamino) -benzophenone Substituted benzophenone compounds;
Heterocyclic group-substituted benzophenone compounds such as 4 ′-(imidazol-1-yl) -benzophenone, 4 ′-(1-pyrazolyl) benzophenone, 4-morpholinobenzophenone;
3-dimethylaminothiobenzophenone, 3-diethylaminothiobenzophenone, 4-dimethylaminothiobenzophenone, 4-diethylaminothiobenzophenone, 4,4'-bis (dimethylamino) -thiobenzophenone, 4,4'-bis (diethylamino)- Dialkylamino-substituted thiobenzophenone compounds such as thiobenzophenone;
Examples include heterocyclic group-substituted thiobenzophenone compounds such as 4 ′-(imidazol-1-yl) -thiobenzophenone, 4 ′-(1-pyrazolyl) thiobenzophenone and 4-morpholinothiobenzophenone.

（式中、ｓ^３は０又は１であり、Ｔ^３０１は炭素原子数１〜１０のヒドロカルビレン基、式（３３−Ｔａ）で表される基、又は、式（３３−Ｔｂ）で表される基を表し、Ｒ^３３５は、窒素原子及び／又は酸素原子を有していてもよいヒドロカルビル基、又は、トリヒドロカルビルシリル基を表し、Ｒ^３３７は、水素原子、又は、ヒドロカルビル基を表す。） As a preferable compound represented by the formula (33), E is an oxygen atom, Z ³⁰¹ is a group represented by the formula (33-Z), and Z ³⁰² is a hydrocarbyl group. ).

(In the formula, s ³ is 0 or 1, and T ³⁰¹ is a hydrocarbylene group having 1 to 10 carbon atoms, a group represented by the formula (33-Ta), or a formula (33-Tb). R ³³⁵ represents a hydrocarbyl group or trihydrocarbylsilyl group optionally having a nitrogen atom and / or an oxygen atom, and R ³³⁷ represents a hydrogen atom or a hydrocarbyl group. )

The definition, illustration and preferred group of T ^{301 in} formula (33-3) are the same as the definition, illustration and preferred group described in formula (33-Z).

The definition, illustration and preferred group of R ^{335 in} formula (33-3) are the same as the definition, illustration and preferred group described in formula (33-A).

^Examples of the hydrocarbyl group for R ³³⁷ include an alkyl group, an alkenyl group, and an aryl group. Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, and a tert-butyl group, and a methyl group is preferable. Examples of the alkenyl group include a vinyl group, an allyl group, a 1-propenyl group, and a 1-methylethenyl group, and a vinyl group is preferable. Examples of the aryl group include a phenyl group, a methylphenyl group, and an ethylphenyl group, and a phenyl group is preferable.

R ³³⁷ is preferably a hydrogen atom, a methyl group, a vinyl group or a phenyl group, more preferably a hydrogen atom or a methyl group.

Examples of the compound represented by the formula (33-3) include the following acrylamide compounds in which s ³ is 0 and R ³³⁷ is a hydrogen atom.
N, N-dimethylacrylamide,
N, N-diethylacrylamide,
N, N-bistrimethylsilylacrylamide,
N, N-di (glycidyl) acrylamide,
N, N-di (tetrahydrofurfuryl) acrylamide,
Morpholinoacrylamide.

As a compound represented by the formula (33-3), the following acrylamide compound, in which s ³ is 1, T ³⁰¹ is a group represented by the formula (33-Tb), and R ³³⁷ is a hydrogen atom, It can be illustrated.
N- (2-dimethylaminoethyl) acrylamide,
N- (3-dimethylaminopropyl) acrylamide,
N- (4-dimethylaminobutyl) acrylamide,
N- (2-diethylaminoethyl) acrylamide,
N- (3-diethylaminopropyl) acrylamide,
N- (4-diethylaminobutyl) acrylamide,
N- (3-bistrimethylsilylaminopropyl) acrylamide,
N- (3-di (glycidyl) aminopropyl) acrylamide,
N- (3-di (tetrahydrofurfuryl) aminopropyl) acrylamide,
N- (3-morpholinopropyl) acrylamide.

Examples of the compound represented by the formula (33-3) include the following methacrylamide compounds in which s ³ is 0 and R ³³⁷ is a methyl group.
N, N-dimethylmethacrylamide,
N, N-diethylmethacrylamide,
N, N-bistrimethylsilylmethacrylamide,
N, N-di (glycidyl) methacrylamide,
N, N-di (tetrahydrofurfuryl) methacrylamide,
Morpholino methacrylamide.

The compound represented by formula (33-3), ^{s 3} is ^1, a ^{group T 301} is represented by the formula ^(33-Tb), next methacrylic ^{R 337} is a methyl group Amide compounds can be exemplified.
N- (2-dimethylaminoethyl) methacrylamide,
N- (3-dimethylaminopropyl) methacrylamide,
N- (4-dimethylaminobutyl) methacrylamide,
N- (2-diethylaminoethyl) methacrylamide,
N- (3-diethylaminopropyl) methacrylamide,
N- (4-diethylaminobutyl) methacrylamide,
N- (3-bistrimethylsilylaminopropyl) methacrylamide,
N- (3-di (glycidyl) aminopropyl) methacrylamide,
N- (3-di (tetrahydrofurfuryl) aminopropyl) methacrylamide,
N- (3-morpholinopropyl) methacrylamide.

As the compound represented by the formula (33-3), the following acrylate compound in which s ³ is 1, T ³⁰¹ is a group represented by the formula (33-Ta), and R ³³⁷ is a hydrogen atom. It can be illustrated.
2-dimethylaminoethyl acrylate,
3-dimethylaminopropyl acrylate,
4-dimethylaminobutyl acrylate,
2-diethylaminoethyl acrylate,
3-diethylaminopropyl acrylate,
4-diethylaminobutyl acrylate,
3-bistrimethylsilylaminopropyl acrylate,
3-di (glycidyl) aminopropyl acrylate,
3-di (tetrahydrofurfuryl) aminopropyl acrylate,
3-morpholinopropyl acrylate.

As a compound represented by the formula (33-3), the following methacrylate compound in which s ³ is 1, T ³⁰¹ is a group represented by the formula (33-Ta), and R ³³⁷ is a methyl group is used. It can be illustrated.
2-dimethylaminoethyl methacrylate,
3-dimethylaminopropyl methacrylate,
4-dimethylaminobutyl methacrylate,
2-diethylaminoethyl methacrylate,
3-diethylaminopropyl methacrylate,
4-diethylaminobutyl methacrylate,
3-bistrimethylsilylaminopropyl methacrylate,
3-di (glycidyl) aminopropyl methacrylate,
3-di (tetrahydrofurfuryl) aminopropyl methacrylate,
3-morpholinopropyl methacrylate.

The compound represented by the formula (33) is preferably a compound represented by the formula (33-3), more preferably s ³ is 1, T ³⁰¹ is the formula (33-Tb), R ³³⁷ is an acrylamide compound or a methacrylamide compound in which a hydrogen atom or a methyl group is present.

More preferably,
N- (3-dimethylaminopropyl) acrylamide,
N- (3-diethylaminopropyl) acrylamide,
N- (3-dimethylaminopropyl) methacrylamide,
N- (3-diethylaminopropyl) methacrylamide.

（式中、ｔ^３は０〜１０の整数を表し、Ｒ^３３４は窒素原子及び／又は酸素原子を有していてもよいヒドロカルビル基、又は、トリヒドロカルビルシリル基を表す。）

（式中、ｕ^３は０〜１０の整数を表し、Ｒ^３３４は窒素原子及び／又は酸素原子を有していてもよいヒドロカルビル基、又は、トリヒドロカルビルシリル基を表す。） Preferred compounds of formula ^(33), a ^{group Z 301} is represented by the formula ^{(33-Z), Z 302} is a hydrocarbylene ^group, hydro of ^{A 303} and ^{Z 302} for ^{Z 301} compound Karubiren group is ^bonded, is a ^{group Z 301} and ^{Z 302} is represented by the formula ^{(33-Z), compound a 303} of ^{a 303} and ^{Z 302} for ^{Z 301} is attached and the like . As the compounds, E is an oxygen atom, a compound represented by the following formula p ³ is 0 (33-4), and a compound represented by the following formula (33-5) below.

(Wherein, t ³ represents an integer of 0, R ³³⁴ is a nitrogen atom and / or hydrocarbyl group optionally having an oxygen atom, or represents a trihydrocarbylsilyl group.)

(Wherein, u ³ is an integer of 0, R ³³⁴ is a nitrogen atom and / or hydrocarbyl group optionally having an oxygen atom, or represents a trihydrocarbylsilyl group.)

Wherein, ^{t 3} and ^{u 3} each represent an integer of 0. From the viewpoint of improving fuel economy, it is preferably 2 or more, and from the viewpoint of improving economy during production, it is preferably 7 or less.

^Wherein the definition of ^{R 334,} exemplary and preferred groups are defined written in ^{R 334} of formula (33-A), the same as examples.

R ³³⁴ is preferably a hydrocarbyl group, more preferably an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 10 carbon atoms.

Examples of the compound represented by the formula (33-4) include β such as N-methyl-β-propiolactam, N- (t-butyl) -β-propiolactam, N-phenyl-β-propiolactam. A propiolactam compound;
1-methyl-2-pyrrolidone, 1- (t-butyl) -2-pyrrolidone, 1-phenyl-2-pyrrolidone, 1- (p-methylphenyl) -2-pyrrolidone, 1- (p-methoxyphenyl)- 2-pyrrolidone, 1-benzyl-2-pyrrolidone, 1-naphthyl-2-pyrrolidone, 1-phenyl-5-methyl-2-pyrrolidone, 1- (t-butyl) -5-methyl-2-pyrrolidone, 1- 2-pyrrolidone compounds such as (t-butyl) -1,3-dimethyl-2-pyrrolidone;
1- (t-butyl) -2-piperidone, 1-phenyl-2-piperidone, 1- (p-methylphenyl) -2-piperidone, 1- (p-methoxyphenyl) -2-piperidone, 1-naphthyl- 2-piperidone compounds such as 2-piperidone;
N-methyl-ε-caprolactam, N-ethyl-ε-caprolactam, N- (n-propyl) -ε-caprolactam, N-phenyl-ε-caprolactam, N- (p-methoxyphenyl) -ε-caprolactam, N An ε-caprolactam compound such as benzyl-ε-caprolactam;
Mention may be made of ω-laurylactam compounds such as N-phenyl-ω-laurylactam.

The compound represented by the formula (33-4) is preferably a 2-pyrrolidone compound or an ε-caprolactam compound, and more preferably 1-hydrocarbyl substituted-2-pyrrolidone or N-hydrocarbyl substituted-ε-caprolactam. More preferred are 1-alkyl substituted-2-pyrrolidone, 1-aryl substituted-2-pyrrolidone, N-alkyl substituted-ε-caprolactam, N-aryl substituted-ε-caprolactam, particularly preferably 1- Phenyl-2-pyrrolidone, N-methyl-ε-caprolactam.

Examples of the compound represented by the formula (33-5) include 1,3-dimethyl-2-imidazolidinone, 1,3-diethyl-2-imidazolidinone, 1,3-di (n-propyl) -2. -Mentioning 1,3-hydrocarbyl-substituted-2-imidazolidinones such as imidazolidinone, 1,3-di (t-butyl) -2-imidazolidinone, 1,3-diphenyl-2-imidazolidinone Can do.

The compound represented by the formula (33-5) is preferably 1,3-substituted-2-imidazolidinone, more preferably 1,3-hydrocarbyl-substituted-2-imidazolidinone, More preferred is 1,3-dialkyl-2-imidazolidinone. The 1,3-dialkyl-2-imidazolidinone is preferably 1,3-dimethyl-2-imidazolidinone, 1,3-diethyl-2-imidazolidinone, 1,3-di (n-propyl). ) -2-imidazolidinone, more preferably 1,3-dimethyl-2-imidazolidinone.

The content of the monomer unit based on the compound represented by the formula (31) is preferably 0.01% by mass or more in order to improve fuel economy per 100% by mass of the conjugated diene polymer. Preferably it is 0.02 mass% or more, More preferably, it is 0.05 mass% or more. In order to improve economic efficiency and wear resistance, the content is preferably 20% by mass or less, more preferably 2% by mass or less, and still more preferably 1% by mass or less.

In the monomer unit based on the compound represented by the formula (31), the groups represented by X ³⁰¹ , X ³⁰² and X ³⁰³ may be a hydroxyl group by hydrolysis or the like.

The content of the monomer unit based on the compound represented by the formula (32) is preferably 0.01% by mass or more per 100% by mass of the conjugated diene polymer in order to improve fuel efficiency and wear resistance. More preferably, it is 0.02 mass% or more, More preferably, it is 0.05 mass% or more. In order to improve economic efficiency and wear resistance, the content is preferably 20% by mass or less, more preferably 2% by mass or less, and still more preferably 1% by mass or less.

The conjugated diene polymer (C) may have a structural unit (vinyl aromatic hydrocarbon unit) based on a vinyl aromatic hydrocarbon in order to improve wear resistance. Examples of the vinyl aromatic hydrocarbon include styrene, α-methylstyrene, vinyl toluene, vinyl naphthalene, divinyl benzene, trivinyl benzene, and divinyl naphthalene. Styrene is preferable.

The content of the vinyl aromatic hydrocarbon unit is 0% by mass or more (the content of the conjugated diene unit is 100% by mass or less), where the total amount of the conjugated diene unit and the vinyl aromatic hydrocarbon unit is 100% by mass. The content is preferably 10% by mass or more (the content of the conjugated diene unit is 90% by mass or less), and more preferably 15% by mass or more (the content of the conjugated diene unit is 85% by mass or less). In order to improve fuel economy, the content of vinyl aromatic hydrocarbon units is preferably 50% by mass or less (the content of conjugated diene units is 50% by mass or more), more preferably 45% by mass or less. (The content of the conjugated diene unit is 55% by mass or more).

The Mooney viscosity (ML _{1 + 4} ) of the conjugated diene polymer (C) is preferably 10 or more, more preferably 20 or more, in order to increase the wear resistance. Moreover, in order to improve workability, Preferably it is 200 or less, More preferably, it is 150 or less. The Mooney viscosity (ML _{1 + 4} ) is measured at 100 ° C. according to JIS K6300 (1994).

The vinyl bond content of the conjugated diene polymer (C) is preferably 70 mol% or less, more preferably 60 mol% or less, in order to improve fuel efficiency by setting the content of the conjugated diene unit to 100 mol%. It is. Moreover, in order to improve wet grip property, Preferably it is 20 mol% or more, More preferably, it is 40 mol% or more, More preferably, it is 50 mol% or more. The vinyl bond amount is determined from the absorption intensity in the vicinity of 910 cm ^−1, which is the absorption peak of the vinyl group, by infrared spectroscopy.

The molecular weight distribution of the conjugated diene polymer (C) is preferably 1 to 5 and more preferably 1 to 2 in order to improve fuel efficiency. The molecular weight distribution is obtained by measuring the number average molecular weight (Mn) and the weight average molecular weight (Mw) by gel permeation chromatography (GPC) method and dividing Mw by Mn.

Suitable method for producing a conjugated diene polymer (C), it is possible to increase the manufacturing method having the following steps A ³ and Step B ^3.
(Step A ³ ): In a hydrocarbon solvent, a monomer component containing a conjugated diene, a compound represented by the above formula (31) and a compound represented by the above formula (32) is polymerized with an alkali metal catalyst. A polymer unit having a monomer unit based on a conjugated diene, a monomer unit based on a compound represented by the above formula (31), and a monomer unit based on a compound represented by the above formula (32). A step of obtaining a polymer having an alkali metal derived from an alkali metal catalyst at least at one end.
(Step B ³ ): A step of reacting the polymer obtained in Step A ³ with the compound (G).

The alkali metal catalyst used in step A ^3, may be mentioned alkali metal, organic alkali metal compound, a complex of an alkali metal and a polar compound, such as an oligomer having an alkali metal. Examples of the alkali metal include lithium, sodium, potassium, rubidium, cesium and the like. Examples of the organic alkali metal compound include ethyl lithium, n-propyl lithium, iso-propyl lithium, n-butyl lithium, sec-butyl lithium, t-octyl lithium, n-decyl lithium, phenyl lithium, 2-naphthyl lithium, 2 -Butylphenyllithium, 4-phenylbutyllithium, cyclohexyllithium, 4-cyclopentyllithium, dimethylaminopropyllithium, diethylaminopropyllithium, t-butyldimethylsiloxypropyllithium, N-morpholinopropyllithium, lithium hexamethyleneimide, lithium pyrrole Zido, lithium piperidide, lithium heptamethylene imide, lithium dodecamethylene imide, 1,4-dilithio-2-butene, sodium naphthalenide, sodium Bifenirido, such as potassium napthalenide can be mentioned. Examples of the complex of the alkali metal and the polar compound include potassium-tetrahydrofuran complex and potassium-diethoxyethane complex, and the oligomer having the alkali metal includes sodium salt of α-methylstyrene tetramer. I can give you. An organic lithium compound or an organic sodium compound is preferable, and an organic lithium compound having 2 to 20 carbon atoms or an organic sodium compound having 2 to 20 carbon atoms is more preferable.

Hydrocarbon solvent used in Step A ³ is a solvent that does not deactivate the organic alkali metal compound catalyst may be mentioned aliphatic hydrocarbons, aromatic hydrocarbons, and alicyclic hydrocarbons. Examples of the aliphatic hydrocarbon include propane, n-butane, iso-butane, n-pentane, iso-pentane, n-hexane, propene, 1-butene, iso-butene, trans-2-butene, cis-2- Examples include butene, 1-pentene, 2-pentene, 1-hexene, 2-hexene and the like. Examples of the aromatic hydrocarbon include benzene, toluene, xylene, and ethylbenzene. Examples of the alicyclic hydrocarbon include cyclopentane and cyclohexane. One or more of these may be used, and the hydrocarbon solvent may be a mixture of various components such as industrial hexane. Preferably, it is a hydrocarbon having 2 to 12 carbon atoms.

In Step A ^3, in a hydrocarbon solvent, the alkali metal catalyst, a conjugated diene, by polymerizing a monomer component including the above formulas (31) and the compound represented by the compound represented by the above formula (32), A polymer having a monomer unit based on a conjugated diene, a monomer unit based on a compound represented by the above formula (31), and a monomer unit based on a compound represented by the above formula (32) is produced. Examples of the conjugated diene include 1,3-butadiene, isoprene, 1,3-pentadiene, 2,3-dimethyl-1,3-butadiene, and 1,3-hexadiene. One or more of these are used. 1,3-butadiene and isoprene are preferred.

The amount of the compound represented by the formula (31) is preferably 0.01% by mass or more in order to improve the fuel efficiency by setting the total amount of the monomer components used in the polymerization to 100% by mass. More preferably, it is 0.02 mass% or more, More preferably, it is 0.05 mass% or more. In order to improve economic efficiency and wear resistance, it is preferably 20% by mass or less, more preferably 2% by mass or less, still more preferably 1% by mass or less, and particularly preferably 0.5% by mass or less. is there.

The amount of the compound represented by the formula (32) is preferably 0.01% by mass in order to improve the fuel efficiency and wear resistance by setting the total amount of the monomer components used in the polymerization to 100% by mass. % Or more, more preferably 0.02 mass% or more, still more preferably 0.05 mass% or more. In order to improve economic efficiency and wear resistance, it is preferably 20% by mass or less, more preferably 2% by mass or less, still more preferably 1% by mass or less, and particularly preferably 0.5% by mass or less. is there.

In Step A ^3, conjugated diene, the compound represented by the formula (31) and the compound represented by the formula in (32) may be carried out polymerization by combining vinyl aromatic hydrocarbon, vinyl aromatic hydrocarbons Examples thereof include styrene, α-methylstyrene, vinyl toluene, vinyl naphthalene, divinyl benzene, trivinyl benzene, divinyl naphthalene and the like. Styrene is preferable.

The amount of vinyl aromatic hydrocarbon used is preferably 10% by mass or more (the amount of conjugated diene used) in order to increase the strength with the total amount of conjugated diene and vinyl aromatic hydrocarbon being 100% by mass. Is 90% by mass or less), more preferably 15% by mass or more (the amount of conjugated diene used is 85% by mass or less). In order to improve fuel efficiency, the amount of vinyl aromatic hydrocarbon used is preferably 50% by mass or less (the amount of conjugated diene used is 50% by mass or more), more preferably 45% by mass or less (conjugated). The amount of diene used is 55% by mass or more).

In the polymerization reaction, the total amount of the conjugated diene, the compound represented by the formula (31), the compound represented by the formula (32) and the vinyl aromatic hydrocarbon is the total amount of the monomer components. In order to increase the strength as 100% by mass, it is preferably 99.9% by mass or more, more preferably 99.95% by mass or more, and still more preferably 100% by mass.

Polymerization reaction is an agent that adjusts the amount of vinyl bonds of conjugated diene units, an agent that adjusts the distribution of monomer units based on monomers other than conjugated diene units and conjugated dienes in the conjugated diene polymer chain , And collectively referred to as “regulators”). Examples of such agents include ether compounds, tertiary amines, and phosphine compounds. Examples of the ether compound include cyclic ethers such as tetrahydrofuran, tetrahydropyran, and 1,4-dioxane; aliphatic monoethers such as diethyl ether and dibutyl ether; ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, and diethylene glycol diethyl ether. And aliphatic diethers such as diethylene glycol dibutyl ether; aromatic ethers such as diphenyl ether and anisole. Examples of the tertiary amine include triethylamine, tripropylamine, tributylamine, N, N, N ′, N′-tetramethylethylenediamine, N, N-diethylaniline, pyridine, quinoline and the like. Examples of the phosphine compound include trimethylphosphine, triethylphosphine, triphenylphosphine, and the like. One or more of these are used.

The polymerization temperature in step ^{A 3} is usually 25 to 100 ° C., preferably from 35 to 90 ° C..
More preferably, it is 50-80 degreeC. The polymerization time is usually 10 minutes to 5 hours.

Step A ³ may be a multi-stage process. For example, it may be a step having the following steps a1, a2, and a3.
(Step a1): In a hydrocarbon solvent, a conjugated diene, a compound represented by the formula (31) and a vinyl aromatic hydrocarbon are polymerized with an alkali metal catalyst, and the alkali metal derived from the catalyst is used as a polymer chain end. Step of obtaining a conjugated diene-based polymer (step a2): adding the compound represented by formula (32) to the hydrocarbon solution obtained in step a1, and converting the compound represented by formula (32) into the step A polymer having a structure in which an alkali metal derived from an alkali metal catalyst is bonded to a monomer unit based on the compound represented by the formula (32) by reacting with a polymer chain end of the conjugated diene polymer obtained in a1. Step of obtaining a conjugated diene polymer having a chain end (step a3): adding the conjugated diene and vinyl aromatic hydrocarbon to the hydrocarbon solution obtained in step a2, Step a2 Step of polymerizing the polymer chain end of the obtained conjugated diene polymer

In Step B ^3, the amount of the compound to be reacted with the polymer prepared in Step A ³ (G) is an alkali metal per mole derived from the organic alkali metal catalyst, usually from 0.1 to 3 mol, preferably 0.5 to 2 mol, and more preferably 0.7 to 1.5 mol.

The conjugated diene polymer (D) according to the fourth aspect of the present invention has a structural unit based on a conjugated diene and a structural unit based on a compound represented by the following formula (41).

（式中、ｍ^４は１〜３の整数を表し、Ｒ^４０１は重合性炭素−炭素二重結合を有するヒドロカルビル基を表し、Ｒ^４０２はヒドロカルビレン基を表し、Ｒ^４０２が複数ある場合、複数あるＲ^４０２は同一でも異なっていてもよく、Ａ^４０１は置換アミノ基を表し、Ａ^４０１が複数ある場合、複数あるＡ^４０１は同一でも異なっていてもよく、Ｒ^４０３はヒドロカルビル基、置換ヒドロカルビル基又は置換アミノ基を表し、Ｒ^４０３が複数ある場合、複数あるＲ^４０３は同一でも異なっていてもよい。）

(In the formula, m ⁴ represents an integer of 1 to 3, R ⁴⁰¹ represents a hydrocarbyl group having a polymerizable carbon-carbon double bond, R ⁴⁰² represents a hydrocarbylene group, and when there are a plurality of R ⁴⁰² , plural ^{R 402} may be the same or ^{different, a 401} represents a substituted amino ^{group, if a 401} there is a plurality, a plurality of ^{a 401} may be the same or ^{different, R 403} is a hydrocarbyl group, substituted hydrocarbyl represents a group or a substituted amino group, if R ⁴⁰³ is more, plural R ⁴⁰³ may be the same or different.)

The conjugated diene polymer (D) according to the fourth aspect of the present invention has a structural unit (conjugated diene unit) based on a conjugated diene. Examples of the conjugated diene include 1,3-butadiene, isoprene, 1,3-pentadiene, 2,3-dimethyl-1,3-butadiene, and 1,3-hexadiene. One or more of these are used. The conjugated diene is preferably 1,3-butadiene or isoprene.

M ^{4 in the} formula (41) is an integer of 1 to 3, and preferably 1 or 2.

^{R 401} of Formula (41) is polymerizable carbon - represents a hydrocarbyl group having a carbon double ^{bond, R 402} represents a hydrocarbylene ^{group, if R 402} is more, plural ^{R 402} is be the same or different at ^{best, a 401} represents a substituted amino ^{group, if a 401} there is a plurality, a plurality of ^{a 401} may be the same or ^{different, R 403} represents a hydrocarbyl group, substituted hydrocarbyl group or a substituted amino ^{group, R 403} When there are a plurality of R ^{403 s} , the plurality of R ^403s may be the same or different.

As used herein, a hydrocarbyl group represents a hydrocarbon residue. A substituted hydrocarbyl group (hydrocarbyl group having a substituent) represents a group in which one or more hydrogen atoms of a hydrocarbon residue are substituted with a substituent, and a hydrocarbylene group represents a divalent hydrocarbon residue. The substituted amino group represents a group in which one or more hydrogen atoms of the amino group are substituted with a substituent.

（式中、ｎ^４は０〜２の整数を表し、Ｒ^４２１、Ｒ^４２２及びＲ^４２３は、それぞれ独立に、水素原子又はヒドロカルビル基を表す。） ^Examples of R ^{401 in the} formula (41) include a group represented by the following formula (42).

(In the formula, n ⁴ represents an integer of 0 to 2, and R ⁴²¹ , R ⁴²² and R ⁴²³ each independently represents a hydrogen atom or a hydrocarbyl group.)

^Examples of the hydrocarbyl group of R ⁴²¹ , R ⁴²² and R ⁴²³ include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, and a neopentyl group. Alkyl groups such as isopentyl group and n-hexyl group; cycloalkyl groups such as cyclohexyl group; aryl groups such as methylphenyl group and ethylphenyl group.

Examples of the group represented by the formula (42) include vinyl groups (R ⁴²¹ , R ⁴²² and R ⁴²³ are hydrogen atoms, n = 0), allyl groups (R ⁴²¹ , R ⁴²² and R ⁴²³ are hydrogen atoms, n = 1 ), 1-propenyl group (R ⁴²¹ is a methyl group, R ⁴²² and R ⁴²³ are hydrogen atoms, n = 0), isopropenyl group (R ⁴²¹ and R ⁴²² are hydrogen atoms, R ⁴²³ is a methyl group, n = 0) A crotyl group (R ⁴²¹ is a methyl group, R ⁴²² and R ⁴²³ are hydrogen atoms, n = 1), and a methallyl group (R ⁴²¹ and R ⁴²² are hydrogen atoms, R ⁴²³ is a methyl group, n = 1).

R ⁴²¹ and R ⁴²² are preferably a hydrogen atom or a methyl group, and more preferably a hydrogen atom.

R ⁴²³ is preferably a hydrogen atom or an alkyl group, more preferably a hydrogen atom or a methyl group.

^{N 4} of the formula (42) represents an integer of 0 to 2. Preferably it is 0 or 1, more preferably 0.

As the formula (42), a vinyl group (R ⁴²¹ , R ⁴²² and R ⁴²³ are hydrogen atoms, n ⁴ = 0) and an allyl group (R ⁴²¹ , R ⁴²² and R ⁴²³ are hydrogen atoms, n ⁴ = 1) are preferable. And more preferably a vinyl group (R ⁴²¹ , R ⁴²² and R ⁴²³ are hydrogen atoms, n ⁴ = 0).

^Examples of the hydrocarbylene group of R ^{402 in} the formula (41) include alkylene groups such as a methylene group, an ethylene group, a trimethylene group, a tetramethylene group, a pentamethylene group, and a hexamethylene group; a phenylene group, a tolylene group, and a xylylene group. An arylene group; and an aralkylene group.

The carbon atom number of the hydrocarbylene group of R ⁴⁰² is preferably 1 to 10, and more preferably 1 to 4.

The hydrocarbylene group for R ⁴⁰² is preferably an alkylene group, more preferably an alkylene group having 1 to 4 carbon atoms, and still more preferably a methylene group or an ethylene group.

（式中、Ｒ^４３１及びＲ^４３２は、窒素原子、酸素原子及びケイ素原子からなる群から選ばれる少なくとも１種の原子を有していてもよい炭素原子数が１〜１０のヒドロカルビル基、シリル基、置換シリル基、あるいは、Ｒ^４３１とＲ^４３２とが結合した炭素原子数が２〜２０の２価基、又は、Ｒ^４３１とＲ^４３２は１つの基であって、窒素原子に二重結合で結合する炭素原子数が２〜２０の基を表す。） ^Examples of the substituted amino group of A ^{401 in} the formula (41) include a group represented by the following formula (43).

(In the formula, R ⁴³¹ and R ⁴³² are a hydrocarbyl group having 1 to 10 carbon atoms and a silyl group, which may have at least one atom selected from the group consisting of a nitrogen atom, an oxygen atom and a silicon atom. , A substituted silyl group, or a divalent group having 2 to 20 carbon atoms in which R ⁴³¹ and R ⁴³² are bonded, or R ⁴³¹ and R ⁴³² are one group, and a double bond to a nitrogen atom Represents a group having 2 to 20 carbon atoms to be bonded.)

^Examples of the hydrocarbyl group of R ⁴³¹ and R ⁴³² include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, n-pentyl group, neopentyl group, isopentyl group. And alkyl groups such as n-hexyl group; cycloalkyl groups such as cyclohexyl group; aryl groups such as phenyl group, methylphenyl group and ethylphenyl group; and aralkyl groups such as benzyl group. Preferably, it is an alkyl group.

The number of carbon atoms of the hydrocarbyl group of R ⁴³¹ and R ⁴³² is preferably 6 or less, more preferably 4 or less, and even more preferably 1 or 2.

^Examples of the hydrocarbyl group having a nitrogen atom of R ⁴³¹ and R ⁴³² include dialkylaminoalkyl groups such as a dimethylaminomethyl group, a dimethylaminoethyl group, a dimethylaminopropyl group, and a diethylaminoethyl group.

The number of carbon atoms of the hydrocarbyl group having a nitrogen atom of R ⁴³¹ and R ⁴³² is preferably 6 or less, more preferably 4 or less. The number of carbon atoms is preferably 3 or more.

^Examples of the hydrocarbyl group having an oxygen atom of R ⁴³¹ and R ⁴³² include an alkoxyalkyl group such as a methoxymethyl group, a methoxyethyl group, a methoxypropyl group, an ethoxymethyl group, and an ethoxyethyl group; an oxacyclo group such as an oxiranyl group and a tetrahydrofuranyl group. An alkyl group; an oxacycloalkylalkyl group such as a glycidyl group and a tetrahydrofurfuryl group. Of these, an oxacycloalkyl group and an oxacycloalkylalkyl group are preferable.

In this specification, the oxacycloalkyl group represents a group in which CH ₂ on the alicyclic ring of the cycloalkyl group is replaced with an oxygen atom, and the oxacycloalkylalkyl group is a group in which a hydrogen atom of the alkyl group is replaced with an oxacycloalkyl group. Represents a group.

The number of carbon atoms of the hydrocarbyl group having an oxygen atom of R ⁴³¹ and R ⁴³² is preferably 6 or less, more preferably 4 or less. The number of carbon atoms is preferably 2 or more.

^Examples of the hydrocarbyl group having a silicon atom of R ⁴³¹ and R ⁴³² include a trialkylsilylalkyl group such as a trimethylsilylmethyl group.

The number of carbon atoms of the hydrocarbyl group having a silicon atom of R ⁴³¹ and R ⁴³² is preferably 6 or less, more preferably 4 or less. The number of carbon atoms is preferably 4 or more.

^Examples of the substituted silyl group for R ⁴³¹ and R ⁴³² include a trialkylsilyl group such as a trimethylsilyl group, a triethylsilyl group, and a t-butyldimethylsilyl group; a trialkoxysilyl group such as a trimethoxysilyl group. Preferably, it is a trialkylsilyl group.

The number of carbon atoms of the substituted silyl group of R ⁴³¹ and R ⁴³² is preferably 3 to 10, more preferably 3 to 6, and further preferably 3.

Examples of the divalent group having 2 to 20 carbon atoms to which R ⁴³¹ and R ⁴³² are bonded include a methylene group, an ethylene group, a trimethylene group, a tetramethylene group, a pentamethylene group, a hexamethylene group, a heptamethylene group, and an octamethylene group. An alkylene group such as a decamethylene group or a dodecamethylene group; an alkenylene group such as a group represented by —CH═CH—CH═CH—; a group represented by —CH ₂ CH ₂ —NH—CH ₂ —, = CH-N = CH- group represented _by, -CH ₂ CH ₂ -N = CH- group represented _by, -CH ₂ CH ₂ CH ₂ -NH- group represented by, -CH = CHCH = A nitrogen-containing group such as a group represented by N—, a group represented by —CH ₂ CH ₂ —NH—CH ₂ CH ₂ —;
Examples thereof include oxygen-containing groups such as a group represented by —CH ₂ CH ₂ —O—CH ₂ CH ₂ — and a group represented by —CH ₂ CH ₂ CH ₂ —O—CH ₂ CH ₂ CH ₂ —.

The number of carbon atoms of the divalent group to which R ⁴³¹ and R ⁴³² are bonded is preferably 2 to 12, and more preferably 2 to 8.

The group having 2 to 20 carbon atoms bonded to the nitrogen atom of R ⁴³¹ and R ^{432 by} a double bond may have at least one atom selected from the group consisting of a nitrogen atom and an oxygen atom. Good group. Examples thereof include an ethylidene group, a propylidene group, a butylidene group, a 1-methylethylidene group, a 1-methylpropylidene group, a 1,3-dimethylbutylidene group, a benzylidene group, and a 4-N, N-dimethylaminobenzylidene group.

The number of carbon atoms of the group bonded to the nitrogen atom of R ⁴³¹ and R ^{432 by} a double bond is preferably 2 to 12, and more preferably 2 to 8.

Examples of the group represented by the formula (43) include an acyclic amino group and a cyclic amino group.

Examples of the acyclic amino group include dimethylamino group, diethylamino group, di (n-propyl) amino group, di (isopropyl) amino group, di (n-butyl) amino group, di (sec-butyl) amino group, di ( dialkylamino groups such as tert-butyl) amino group, di (neopentyl) amino group, ethylmethylamino group;
Di (alkoxyalkyl) amino groups such as di (methoxymethyl) amino group, di (methoxyethyl) amino group, di (ethoxymethyl) amino group, di (ethoxyethyl) amino group;
Examples thereof include di (trialkylsilyl) amino groups such as di (trimethylsilyl) amino group and di (t-butyldimethylsilyl) amino group.
In addition, di (oxacycloalkyl) amino groups such as di (oxiranyl) amino group and di (tetrahydrofuranyl) amino group; di (oxacycloalkylalkyl) such as di (glycidyl) amino group and di (tetrahydrofurfuryl) amino group ) Amino group.
Furthermore, an ethylideneamino group, 1-methylpropylideneamino group, 1,3-dimethylbutylideneamino group, 1-methylethylideneamino group, 4-N, N-dimethylaminobenzylideneamino group can be mentioned.

Examples of the cyclic amino group include 1-aziridinyl group, 1-azetidinyl group, 1-pyrrolidinyl group, 1-piperidinyl group, 1-hexamethyleneimino group, 1-heptamethyleneimino group, 1-octamethyleneimino group, 1- Examples thereof include 1-polymethyleneimino group such as decamethyleneimino group and 1-dodecamethyleneimino group. Moreover, 1-pyrrolyl group, 1-imidazolidinyl group, 1-imidazolyl group, 4,5-dihydro-1-imidazolyl group, 1-pyrazolidinyl group, 1-pyrazolyl group, 1-piperazinyl group, morpholino group and the like can be mentioned.

The substituted amino group represented by the formula (43) is preferably a dialkylamino group or a 1-polymethyleneimino group, and more preferably a 1-polymethyleneimino group.

R ^{403 in the} formula (41) represents a hydrocarbyl group, a substituted hydrocarbyl group or a substituted amino group.

^Examples of the hydrocarbyl group of R ⁴⁰³ include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, n-pentyl group, neopentyl group, isopentyl group, n- Examples thereof include alkyl groups such as hexyl group; cycloalkyl groups such as cyclohexyl group; aryl groups such as phenyl group, methylphenyl group and ethylphenyl group; and aralkyl groups such as benzyl group. The hydrocarbyl group is preferably an alkyl group.

The number of carbon atoms of the hydrocarbyl group of R ⁴⁰³ is preferably 1 to 4, more preferably 1 or 2.

^Examples of the substituted hydrocarbyl group of R ⁴⁰³ include alkoxyalkyl groups such as a methoxymethyl group, a methoxyethyl group, an ethoxymethyl group, and an ethoxyethyl group. The substituted hydrocarbyl group is preferably an alkoxyalkyl group, and more preferably an alkoxyalkyl group having 2 to 4 carbon atoms.

The number of carbon atoms of the substituted hydrocarbyl group of R ⁴⁰³ is preferably 1 to 4.

^Examples of the substituted amino group for R ⁴⁰³ include a dimethylamino group, a diethylamino group, a di (n-propyl) amino group, a di (isopropyl) amino group, a di (n-butyl) amino group, a di (sec-butyl) amino group, Dialkylamino groups such as di (tert-butyl) amino group, di (neopentyl) amino group, ethylmethylamino group; aralkylamino groups such as benzylamino group; arylamino groups such as phenylamino group; diaryls such as diphenylamino group Amino group; alkylideneamino group such as ethylideneamino group, 1-methylethylideneamino group, 2-methylpropylideneamino group, 1,3-dimethylbutylideneamino group; 1-aziridinyl group, 1-azetidinyl group, 1-pyrrolidinyl Group, 1-piperidinyl group, 1-hexamethyleneimino group, 1-heptame Cyclic amino such as thylene imino group, 1-pyrrolyl group, 1-imidazolidinyl group, 1-imidazolyl group, 4,5-dihydro-1-imidazolyl group, 1-pyrazolidinyl group, 1-pyrazolyl group, 1-piperazinyl group, morpholino group Group.

The substituted amino group for R ⁴⁰³ is preferably an acyclic amino group, and more preferably a dialkylamino group.

R ⁴⁰³ is preferably a hydrocarbyl group or a substituted hydrocarbyl group, and more preferably a hydrocarbyl group.

As the compound represented by the formula (41), R ⁴⁰¹ is a group represented by the formula (42), m ⁴ is 1, and A ⁴⁰¹ is an acyclic amino group represented by the formula (43). There are certain compounds.
As the compound,
(Dialkylamino) alkyldialkylvinylsilane,
(Dialkylamino) alkyldialkylallylsilane,
(Dialkylamino) alkyldialkyl-1-propenylsilane,
(Dialkylamino) alkyldialkylisopropenylsilane,
(Dialkylamino) alkyldialkylcrotylsilane,
(Dialkylamino) alkyldialkylmethallylsilane.
Specific compounds will be exemplified in the following paragraphs.

[1] (Dialkylamino) alkyldialkylvinylsilane:
(Dimethylamino) methyldimethylvinylsilane, (diethylamino) methyldimethylvinylsilane, (di-n-propylamino) methyldimethylvinylsilane, (di-n-butylamino) methyldimethylvinylsilane, (di-t-butylamino) methyldimethylvinylsilane ,
(Methylethylamino) methyldimethylvinylsilane, (methyl-n-propylamino) methyldimethylvinylsilane, (ethyl-n-propylamino) methyldimethylvinylsilane,
(Dimethylamino) methylmethylethylvinylsilane, (dimethylamino) methylmethyl-n-propylvinylsilane, (dimethylamino) methylethyl-n-propylvinylsilane,

2- (dimethylamino) ethyldimethylvinylsilane, 2- (diethylamino) ethyldimethylvinylsilane, 2- (di-n-propylamino) ethyldimethylvinylsilane, 2- (di-n-butylamino) ethyldimethylvinylsilane, 2- ( Di-t-butylamino) ethyldimethylvinylsilane,
2- (methylethylamino) ethyldimethylvinylsilane, 2- (methyln-propylamino) ethyldimethylvinylsilane, 2- (ethyl-n-propylamino) ethyldimethylvinylsilane,
(Dimethylamino) ethylmethylethylvinylsilane, (dimethylamino) ethylmethyl-n-propylvinylsilane, dimethylamino) ethylethyl-n-propylvinylsilane,

3- (dimethylamino) -n-propyldimethylvinylsilane, 3- (diethylamino) -n-propyldimethylvinylsilane, 3- (di-n-propylamino) -n-propyldimethylvinylsilane, 3- (di-n-butyl) Amino) -n-propyldimethylvinylsilane, 3- (di-t-butylamino) -n-propyldimethylvinylsilane,
3- (methylethylamino) -n-propyldimethylvinylsilane, 3- (methyln-propylamino) -n-propyldimethylvinylsilane, 3- (ethyl-n-propylamino) -n-propyldimethylvinylsilane,
(Dimethylamino) -n-propylmethylethylvinylsilane, (dimethylamino) -n-propylmethyl-n-propylvinylsilane, (dimethylamino) -n-propylethyl-n-propylvinylsilane.

[2] (Dialkylamino) alkyldialkylallylsilane:
(Dimethylamino) methyldimethylallylsilane, (diethylamino) methyldimethylallylsilane, (di-n-propylamino) methyldimethylallylsilane, (di-n-butyl) aminomethyldimethylallylsilane, (di-t-butyl) aminomethyldimethylallylsilane ,
(Methylethylamino) methyldimethylallylsilane, (methyl-n-propylamino) methyldimethylallylsilane, (ethyl-n-propylamino) methyldimethylallylsilane,
(Dimethylamino) methylmethylethylallylsilane, (dimethylamino) methylmethyl-n-propylallylsilane, (dimethylamino) methylethyl-n-propylallylsilane,

2- (dimethylamino) ethyldimethylallylsilane, 2- (diethylamino) ethyldimethylallylsilane, 2- (di-n-propylamino) ethyldimethylallylsilane, 2- (di-n-butylamino) ethyldimethylallylsilane, 2- ( Di-t-butylamino) ethyldimethylallylsilane,
2- (methylethylamino) ethyldimethylallylsilane, 2- (methyln-propylamino) ethyldimethylallylsilane, 2- (ethyl-n-propylamino) ethyldimethylallylsilane,
(Dimethylamino) ethylmethylethylallylsilane, (dimethylamino) ethylmethyl-n-propylallylsilane, (dimethylamino) ethylethyl-n-propylallylsilane,

3- (dimethylamino) -n-propyldimethylallylsilane, 3- (diethylamino) -n-propyldimethylallylsilane, 3- (di-n-propylamino) -n-propyldimethylallylsilane, 3- (di-n-butyl) Amino) -n-propyldimethylallylsilane, 3- (di-t-butylamino) -n-propyldimethylallylsilane,
3- (methylethylamino) -n-propyldimethylallylsilane, 3- (methyln-propylamino) -n-propyldimethylallylsilane, 3- (ethyl-n-propylamino) -n-propyldimethylallylsilane,
(Dimethylamino) -n-propylmethylethylallylsilane, (dimethylamino) -n-propylmethyl-n-propylallylsilane, (dimethylamino) -n-propylethyl-n-propylallylsilane.

[3] (Dialkylamino) alkyldialkyl-1-propenylsilane:
(Dimethylamino) methyldimethyl-1-propenylsilane, (diethylamino) methyldimethyl-1-propenylsilane, (di-n-propylamino) methyldimethyl-1-propenylsilane, (di-n-butyl) aminomethyldimethyl- 1-propenylsilane, (di-t-butyl) aminomethyldimethyl-1-propenylsilane,
(Methylethylamino) methyldimethyl-1-propenylsilane, (methyl-n-propylamino) methyldimethyl-1-propenylsilane, (ethyl-n-propylamino) methyldimethyl-1-propenylsilane,
(Dimethylamino) methylmethylethyl-1-propenylsilane, (dimethylamino) methylmethyl-n-propyl1-propenylsilane, (dimethylamino) methylethyl-n-propyl1-propenylsilane,

2- (dimethylamino) ethyldimethyl-1-propenylsilane, 2- (diethylamino) ethyldimethyl-1-propenylsilane, 2- (di-n-propylamino) ethyldimethyl-1-propenylsilane, 2- (di- n-butylamino) ethyldimethyl-1-propenylsilane, 2- (di-t-butylamino) ethyldimethyl-1-propenylsilane,
2- (methylethylamino) ethyldimethyl-1-propenylsilane, 2- (methyln-propylamino) ethyldimethyl-1-propenylsilane, 2- (ethyl-n-propylamino) ethyldimethyl-1-propenylsilane,
(Dimethylamino) ethylmethylethyl-1-propenylsilane, (dimethylamino) ethylmethyl-n-propyl1-propenylsilane, (dimethylamino) ethylethyl-n-propyl1-propenylsilane,

3- (dimethylamino) -n-propyldimethyl-1-propenylsilane, 3- (diethylamino) -n-propyldimethyl-1-propenylsilane, 3- (di-n-propylamino) -n-propyldimethyl-1 -Propenylsilane, 3- (di-n-butylamino) -n-propyldimethyl-1-propenylsilane, 3- (di-t-butylamino) -n-propyldimethyl-1-propenylsilane,
3- (methylethylamino) -n-propyldimethyl-1-propenylsilane, 3- (methyl-n-propylamino) -n-propyldimethyl-1-propenylsilane, 3- (ethyl-n-propylamino)- n-propyldimethyl-1-propenylsilane,
(Dimethylamino) -n-propylmethylethyl-1-propenylsilane, (dimethylamino) -n-propylmethyl-n-propyl1-propenylsilane, (dimethylamino) -n-propylethyl-n-propyl1-propenyl Silane.

[4] (Dialkylamino) alkyldialkylisopropenylsilane:
(Dimethylamino) methyldimethylisopropenylsilane, (diethylamino) methyldimethylisopropenylsilane, (di-n-propylamino) methyldimethylisopropenylsilane, (di-n-butyl) aminomethyldimethylisopropenylsilane, (di- t-butyl) aminomethyldimethylisopropenylsilane,
(Methylethylamino) methyldimethylisopropenylsilane, (methyl-n-propylamino) methyldimethylisopropenylsilane, (ethyl-n-propylamino) methyldimethylisopropenylsilane,
(Dimethylamino) methylmethylethylisopropenylsilane, (dimethylamino) methylmethyl-n-propylisopropenylsilane, (dimethylamino) methylethyl-n-propylisopropenylsilane,

2- (dimethylamino) ethyldimethylisopropenylsilane, 2- (diethylamino) ethyldimethylisopropenylsilane, 2- (di-n-propylamino) ethyldimethylisopropenylsilane, 2- (di-n-butylamino) ethyl Dimethyl isopropenyl silane, 2- (di-t-butylamino) ethyl dimethyl isopropenyl silane,
2- (methylethylamino) ethyldimethylisopropenylsilane, 2- (methyln-propylamino) ethyldimethylisopropenylsilane, 2- (ethyl-n-propylamino) ethyldimethylisopropenylsilane,
(Dimethylamino) ethylmethylethylisopropenylsilane, (dimethylamino) ethylmethyl-n-propylisopropenylsilane, (dimethylamino) ethylethyl-n-propylisopropenylsilane,

3- (dimethylamino) -n-propyldimethylisopropenylsilane, 3- (diethylamino) -n-propyldimethylisopropenylsilane, 3- (di-n-propylamino) -n-propyldimethylisopropenylsilane, 3- (Di-n-butylamino) -n-propyldimethylisopropenylsilane, 3- (di-t-butylamino) -n-propyldimethylisopropenylsilane,
3- (methylethylamino) -n-propyldimethylisopropenylsilane, 3- (methyln-propylamino) -n-propyldimethylisopropenylsilane, 3- (ethyl-n-propylamino) -n-propyldimethyliso Propenylsilane,
(Dimethylamino) -n-propylmethylethylisopropenylsilane, (dimethylamino) -n-propylmethyl-n-propylisopropenylsilane, (dimethylamino) -n-propylethyl-n-propylisopropenylsilane.

[5] (Dialkylamino) alkyldialkylcrotylsilane:
(Dimethylamino) methyldimethylcrotylsilane, (diethylamino) methyldimethylcrotylsilane, (di-n-propylamino) methyldimethylcrotylsilane, (di-n-butyl) aminomethyldimethylcrotylsilane, (di- t-butyl) aminomethyldimethylcrotylsilane,
(Methylethylamino) methyldimethylcrotylsilane, (methyl-n-propylamino) methyldimethylcrotylsilane, (ethyl-n-propylamino) methyldimethylcrotylsilane,
(Dimethylamino) methylmethylethylcrotylsilane, (dimethylamino) methylmethyl-n-propylcrotylsilane, (dimethylamino) methylethyl-n-propylcrotylsilane,

2- (dimethylamino) ethyldimethylcrotylsilane, 2- (diethylamino) ethyldimethylcrotylsilane, 2- (di-n-propylamino) ethyldimethylcrotylsilane, 2- (di-n-butylamino) ethyl Dimethylcrotylsilane, 2- (di-t-butylamino) ethyldimethylcrotylsilane,
2- (methylethylamino) ethyldimethylcrotylsilane, 2- (methyln-propylamino) ethyldimethylcrotylsilane, 2- (ethyl-n-propylamino) ethyldimethylcrotylsilane,
(Dimethylamino) ethylmethylethylcrotylsilane, (dimethylamino) ethylmethyl-n-propylcrotylsilane, (dimethylamino) ethylethyl-n-propylcrotylsilane,

3- (dimethylamino) -n-propyldimethylcrotylsilane, 3- (diethylamino) -n-propyldimethylcrotylsilane, 3- (di-n-propylamino) -n-propyldimethylcrotylsilane, 3- (Di-n-butylamino) -n-propyldimethylcrotylsilane, 3- (di-t-butylamino) -n-propyldimethylcrotylsilane,
3- (methylethylamino) -n-propyldimethylcrotylsilane, 3- (methyl-n-propylamino) -n-propyldimethylcrotylsilane, 3- (ethyl-n-propylamino) -n-propyldimethyl Crotylsilane,
(Dimethylamino) -n-propylmethylethylcrotylsilane, (dimethylamino) -n-propylmethyl-n-propylcrotylsilane, (dimethylamino) -n-propylethyl-n-propylcrotylsilane.

[6] (Dialkylamino) alkyldialkylmethallylsilane:
(Dimethylamino) methyldimethylmethallylsilane, (diethylamino) methyldimethylmethallylsilane, (di-n-propylamino) methyldimethylmethallylsilane, (di-n-butyl) aminomethyldimethylmethallylsilane, (di- t-butyl) aminomethyldimethylmethallylsilane,
(Methylethylamino) methyldimethylmethallylsilane, (methyl-n-propylamino) methyldimethylmethallylsilane, (ethyl-n-propylamino) methyldimethylmethallylsilane,
(Dimethylamino) methylmethylethylmethallylsilane, (dimethylamino) methylmethyl-n-propylmethallylsilane, (dimethylamino) methylethyl-n-propylmethallylsilane,

2- (dimethylamino) ethyldimethylmethallylsilane, 2- (diethylamino) ethyldimethylmethallylsilane, 2- (diethylamino) ethyldimethylmethallylsilane, 2- (di-n-propylamino) ethyldimethylmethallylsilane, 2- (di-n-butylamino) ethyldimethylmethallylsilane, 2- (di-t-butylamino) ethyldimethylmethallylsilane,
2- (methylethylamino) ethyldimethylmethallylsilane, 2- (methyln-propylamino) ethyldimethylmethallylsilane, 2- (ethyl-n-propylamino) ethyldimethylmethallylsilane,
(Dimethylamino) ethylmethylethylmethallylsilane, (dimethylamino) ethylmethyl-n-propylmethallylsilane, (dimethylamino) ethylethyl-n-propylmethallylsilane,

3- (dimethylamino) -n-propyldimethylmethallylsilane, 3- (diethylamino) -n-propyldimethylmethallylsilane, 3- (di-n-propylamino) -n-propyldimethylmethallylsilane, 3- (Di-n-butylamino) -n-propyldimethylmethallylsilane, 3- (di-t-butylamino) -n-propyldimethylmethallylsilane,
3- (methylethylamino) -n-propyldimethylmethallylsilane, 3- (methyl-n-propylamino) -n-propyldimethylmethallylsilane, 3- (ethyl-n-propylamino) -n-propyldimethyl Methallylsilane,
(Dimethylamino) -n-propylmethylethylmethallylsilane, (dimethylamino) -n-propylmethyl-n-propylmethallylsilane, (dimethylamino) -n-propylethyl-n-propylmethallylsilane.

As the compound represented by the formula (41), R ⁴⁰¹ is a group represented by the formula (42), m ⁴ is 1, and A ⁴⁰¹ is a cyclic amino group represented by the formula (43). Compounds.
As the compound,
1-polymethyleneiminoalkyldialkylvinylsilane,
1-polymethyleneiminoalkyldialkylallylsilane,
1-polymethyleneiminoalkyldialkyl-1-propenylsilane,
1-polymethyleneiminoalkyldialkylisopropenylsilane,
1-polymethyleneiminoalkyldialkylcrotylsilane,
An example is 1-polymethyleneiminoalkyldialkylmethallylsilane.
Specific compounds will be exemplified in the following paragraphs.

[7] 1-polymethyleneiminoalkyldialkylvinylsilane:
1-aziridinylmethyldimethylvinylsilane, 2- (1-aziridinyl) ethyldimethylvinylsilane, 3- (1-aziridinyl) -n-propyldimethylvinylsilane,
1-aziridinylmethyldiethylvinylsilane,
1-aziridinylmethyldi-n-propylvinylsilane,
2- (1-aziridinyl) ethyldiethylvinylsilane,
2- (1-aziridinyl) ethyldi-n-propylvinylsilane,
3- (1-aziridinyl) -n-propyldiethylvinylsilane,
3- (1-aziridinyl) -n-propyldi-n-propylvinylsilane,

1-azeridinylmethyldimethylvinylsilane, 2- (1-azelidinyl) ethyldimethylvinylsilane, 3- (1-azeridinyl) -n-propyldimethylvinylsilane,
1-azeridinylmethyldiethylvinylsilane,
1-azeridinylmethyldi-n-propylvinylsilane,
2- (1-azeridinyl) ethyldiethylvinylsilane,
2- (1-azeridinyl) ethyldi-n-propylvinylsilane,
3- (1-azeridinyl) -n-propyldiethylvinylsilane,
3- (1-azeridinyl) -n-propyldi-n-propylvinylsilane,

Dimethyl-1-pyrrolidinylmethylvinylsilane, dimethyl-2- (1-pyrrolidinyl) ethylvinylsilane, 3dimethyl- (1-pyrrolidinyl) -n-propylvinylsilane,
Diethyl-1-pyrrolidinylmethylvinylsilane,
1-pyrrolidinylmethyldi-n-propylvinylsilane,
Diethyl-2- (1-pyrrolidinyl) ethylvinylsilane,
2- (1-pyrrolidinyl) ethyldi-n-propylvinylsilane,
Diethyl-3- (1-pyrrolidinyl) -n-propylvinylsilane,
3- (1-pyrrolidinyl) -n-propyldi-n-propylvinylsilane,

Dimethyl-1-piperidinylmethylvinylsilane, dimethyl-2- (1-piperidinyl) ethylvinylsilane, dimethyl-3- (1-piperidinyl) -n-propylvinylsilane,
Diethyl-1-piperidinylmethylvinylsilane,
1-piperidinylmethyldi-n-propylvinylsilane,
2- (1-piperidinyl) ethyldiethylvinylsilane,
2- (1-piperidinyl) ethyldi-n-propylvinylsilane,
Diethyl-3- (1-piperidinyl) -n-propylvinylsilane,
3- (1-piperidinyl) -n-propyldi-n-propylvinylsilane,

1-hexamethyleneiminomethyldimethylvinylsilane, 2- (1-hexamethyleneimino) ethyldimethylvinylsilane, 3- (1-hexamethyleneimino) -n-propyldimethylvinylsilane,
Diethyl-1-hexamethyleneiminomethylvinylsilane,
1-hexamethyleneiminomethyldi-n-propylvinylsilane,
Diethyl-2- (1-hexamethyleneimino) ethylvinylsilane,
2- (1-hexamethyleneimino) ethyldi-n-propylvinylsilane,
Diethyl-3- (1-hexamethyleneimino) -n-propylvinylsilane,
3- (1-hexamethyleneimino) -n-propyldi-n-propylvinylsilane,

1-heptamethyleneiminomethyldimethylvinylsilane, 2- (1-heptamethyleneimino) ethyldimethylvinylsilane, 3- (1-heptamethyleneimino) -n-propyldimethylvinylsilane,
Diethyl-1-heptamethyleneiminomethylvinylsilane,
1-heptamethyleneiminomethyldi-n-propylvinylsilane,
Diethyl-2- (1-heptamethyleneimino) ethylvinylsilane,
2- (1-heptamethyleneimino) ethyldi-n-propylvinylsilane,
Diethyl-3- (1-heptamethyleneimino) -n-propylvinylsilane,
3- (1-heptamethyleneimino) -n-propyldi-n-propylvinylsilane,

Dimethyl-1-octamethyleneiminomethylvinylsilane, dimethyl-2- (1-octamethyleneimino) ethylvinylsilane, dimethyl-3- (1-octamethyleneimino) -n-propylvinylsilane,
Diethyl-1-octamethyleneiminomethylvinylsilane,
1-octamethyleneiminomethyldi-n-propylvinylsilane,
Diethyl-2- (1-octamethyleneimino) ethylvinylsilane,
2- (1-octamethyleneimino) ethyldi-n-propylvinylsilane,
Diethyl-3- (1-octamethyleneimino) -n-propylvinylsilane,
3- (1-octamethyleneimino) -n-propyldi-n-propylvinylsilane,

1-decamethyleneiminomethyldimethylvinylsilane, 2- (1-decamethyleneimino) ethyldimethylvinylsilane, 3- (1-decamethyleneimino) -n-propyldimethylvinylsilane,
1-decamethyleneiminomethyldiethylvinylsilane,
1-decamethyleneiminomethyldi-n-propylvinylsilane,
2- (1-decamethyleneimino) ethyldiethylvinylsilane,
2- (1-decamethyleneimino) ethyldi-n-propylvinylsilane,
3- (1-Decamethyleneimino) -n-propyldiethylvinylsilane,
3- (1-decamethyleneimino) -n-propyldi-n-propylvinylsilane,

1-dodecamethyleneiminomethyldimethylvinylsilane, 2- (1-dodecamethyleneimino) ethyldimethylvinylsilane, 3- (1-dodecamethyleneimino) -n-propyldimethylvinylsilane,
1-dodecamethyleneiminomethyldiethylvinylsilane,
1-dodecamethyleneiminomethyldi-n-propylvinylsilane,
2- (1-dodecamethyleneimino) ethyldiethylvinylsilane,
2- (1-dodecamethyleneimino) ethyldi-n-propylvinylsilane,
3- (1-dodecamethyleneimino) -n-propyldiethylvinylsilane,
3- (1-dodecamethyleneimino) -n-propyldi-n-propylvinylsilane.

[8] 1-polymethyleneiminoalkyldialkylallylsilane:
1-aziridinylmethyldimethylallylsilane, 2- (1-aziridinyl) ethyldimethylallylsilane, 3- (1-aziridinyl) -n-propyldimethylallylsilane,
1-aziridinylmethyldiethylallylsilane,
1-aziridinylmethyldi-n-propylallylsilane,
2- (1-aziridinyl) ethyldiethylallylsilane,
2- (1-aziridinyl) ethyldi-n-propylallylsilane,
3- (1-aziridinyl) -n-propyldiethylallylsilane,
3- (1-aziridinyl) -n-propyldi-n-propylallylsilane,

1-azeridinylmethyldimethylallylsilane, 2- (1-azeridinyl) ethyldimethylallylsilane, 3- (1-azeridinyl) -n-propyldimethylallylsilane,
1-azeridinylmethyldiethylallylsilane,
1-azeridinylmethyldi-n-propylallylsilane,
2- (1-azelidinyl) ethyldiethylallylsilane,
2- (1-azeridinyl) ethyldi-n-propylallylsilane,
3- (1-azelidinyl) -n-propyldiethylallylsilane,
3- (1-azelidinyl) -n-propyldi-n-propylallylsilane,

Dimethyl-1-pyrrolidinylmethylallylsilane, dimethyl-2- (1-pyrrolidinyl) ethylallylsilane, 3dimethyl- (1-pyrrolidinyl) -n-propylallylsilane,
Diethyl-1-pyrrolidinylmethylallylsilane,
1-pyrrolidinylmethyldi-n-propylallylsilane,
Diethyl-2- (1-pyrrolidinyl) ethylallylsilane,
2- (1-pyrrolidinyl) ethyldi-n-propylallylsilane,
Diethyl-3- (1-pyrrolidinyl) -n-propylallylsilane,
3- (1-pyrrolidinyl) -n-propyldi-n-propylallylsilane,

Dimethyl-1-piperidinylmethylallylsilane, dimethyl-2- (1-piperidinyl) ethylallylsilane, dimethyl-3- (1-piperidinyl) -n-propylallylsilane,
Diethyl-1-piperidinylmethylallylsilane,
1-piperidinylmethyldi-n-propylallylsilane,
2- (1-piperidinyl) ethyldiethylallylsilane,
2- (1-piperidinyl) ethyldi-n-propylallylsilane,
Diethyl-3- (1-piperidinyl) -n-propylallylsilane,
3- (1-piperidinyl) -n-propyldi-n-propylallylsilane,

1-hexamethyleneiminomethyldimethylallylsilane, 2- (1-hexamethyleneimino) ethyldimethylallylsilane, 3- (1-hexamethyleneimino) -n-propyldimethylallylsilane,
Diethyl-1-hexamethyleneiminomethylallylsilane,
1-hexamethyleneiminomethyldi-n-propylallylsilane,
Diethyl-2- (1-hexamethyleneimino) ethylallylsilane,
2- (1-hexamethyleneimino) ethyldi-n-propylallylsilane,
Diethyl-3- (1-hexamethyleneimino) -n-propylallylsilane,
3- (1-hexamethyleneimino) -n-propyldi-n-propylallylsilane,

1-heptamethyleneiminomethyldimethylallylsilane, 2- (1-heptamethyleneimino) ethyldimethylallylsilane, 3- (1-heptamethyleneimino) -n-propyldimethylallylsilane,
Diethyl-1-heptamethyleneiminomethylallylsilane,
1-heptamethyleneiminomethyldi-n-propylallylsilane,
Diethyl-2- (1-heptamethyleneimino) ethylallylsilane,
2- (1-heptamethyleneimino) ethyldi-n-propylallylsilane,
Diethyl-3- (1-heptamethyleneimino) -n-propylallylsilane,
3- (1-heptamethyleneimino) -n-propyldi-n-propylallylsilane,

Dimethyl-1-octamethyleneiminomethylallylsilane, dimethyl-2- (1-octamethyleneimino) ethylallylsilane, dimethyl-3- (1-octamethyleneimino) -n-propylallylsilane,
Diethyl-1-octamethyleneiminomethylallylsilane,
1-octamethyleneiminomethyldi-n-propylallylsilane,
Diethyl-2- (1-octamethyleneimino) ethylallylsilane,
2- (1-octamethyleneimino) ethyldi-n-propylallylsilane,
Diethyl-3- (1-octamethyleneimino) -n-propylallylsilane,
3- (1-octamethyleneimino) -n-propyldi-n-propylallylsilane,

1-decamethyleneiminomethyldimethylallylsilane, 2- (1-decamethyleneimino) ethyldimethylallylsilane, 3- (1-decamethyleneimino) -n-propyldimethylallylsilane,
1-decamethyleneiminomethyldiethylallylsilane,
1-decamethyleneiminomethyldi-n-propylallylsilane,
2- (1-decamethyleneimino) ethyldiethylallylsilane,
2- (1-decamethyleneimino) ethyldi-n-propylallylsilane,
3- (1-decamethyleneimino) -n-propyldiethylallylsilane,
3- (1-decamethyleneimino) -n-propyldi-n-propylallylsilane,

1-dodecamethyleneiminomethyldimethylallylsilane, 2- (1-dodecamethyleneimino) ethyldimethylallylsilane, 3- (1-dodecamethyleneimino) -n-propyldimethylallylsilane,
1-dodecamethyleneiminomethyldiethylallylsilane,
1-dodecamethyleneiminomethyldi-n-propylallylsilane,
2- (1-dodecamethyleneimino) ethyldiethylallylsilane,
2- (1-dodecamethyleneimino) ethyldi-n-propylallylsilane,
3- (1-dodecamethyleneimino) -n-propyldiethylallylsilane,
3- (1-dodecamethyleneimino) -n-propyldi-n-propylallylsilane.

[9] 1-polymethyleneiminoalkyldialkyl-1-propenylsilane:
1-aziridinylmethyldimethyl-1-propenylsilane, 2- (1-aziridinyl) ethyldimethyl-1-propenylsilane, 3- (1-aziridinyl) -n-propyldimethyl-1-propenylsilane,
1-aziridinylmethyldiethyl-1-propenylsilane,
1-aziridinylmethyldi-n-propyl 1-propenylsilane,
2- (1-aziridinyl) ethyldiethyl-1-propenylsilane,
2- (1-aziridinyl) ethyldi-n-propyl 1-propenylsilane,
3- (1-aziridinyl) -n-propyldiethyl-1-propenylsilane,
3- (1-aziridinyl) -n-propyldi-n-propyl 1-propenylsilane,

1-azeridinylmethyldimethyl-1-propenylsilane, 2- (1-azeridinyl) ethyldimethyl-1-propenylsilane, 3- (1-azeridinyl) -n-propyldimethyl-1-propenylsilane,
1-azeridinylmethyldiethyl-1-propenylsilane,
1-azeridinylmethyldi-n-propyl 1-propenylsilane,
2- (1-azelidinyl) ethyldiethyl-1-propenylsilane,
2- (1-azeridinyl) ethyldi-n-propyl 1-propenylsilane,
3- (1-azelidinyl) -n-propyldiethyl-1-propenylsilane,
3- (1-azelidinyl) -n-propyldi-n-propyl 1-propenylsilane,

Dimethyl-1-pyrrolidinylmethyl-1-propenylsilane, dimethyl-2- (1-pyrrolidinyl) ethyl-1-propenylsilane, 3dimethyl- (1-pyrrolidinyl) -n-propyl 1-propenylsilane,
Diethyl-1-pyrrolidinylmethyl-1-propenylsilane,
1-pyrrolidinylmethyldi-n-propyl 1-propenylsilane,
Diethyl-2- (1-pyrrolidinyl) ethyl-1-propenylsilane,
2- (1-pyrrolidinyl) ethyldi-n-propyl 1-propenylsilane,
Diethyl-3- (1-pyrrolidinyl) -n-propyl 1-propenylsilane,
3- (1-pyrrolidinyl) -n-propyldi-n-propyl 1-propenylsilane,

Dimethyl-1-piperidinylmethyl-1-propenylsilane, dimethyl-2- (1-piperidinyl) ethyl-1-propenylsilane, dimethyl-3- (1-piperidinyl) -n-propyl 1-propenylsilane,
Diethyl-1-piperidinylmethyl-1-propenylsilane,
1-piperidinylmethyldi-n-propyl 1-propenylsilane,
2- (1-piperidinyl) ethyldiethyl-1-propenylsilane,
2- (1-piperidinyl) ethyldi-n-propyl 1-propenylsilane,
Diethyl-3- (1-piperidinyl) -n-propyl 1-propenylsilane,
3- (1-piperidinyl) -n-propyldi-n-propyl 1-propenylsilane,

1-hexamethyleneiminomethyldimethyl-1-propenylsilane, 2- (1-hexamethyleneimino) ethyldimethyl-1-propenylsilane, 3- (1-hexamethyleneimino) -n-propyldimethyl-1-propenylsilane,
Diethyl-1-hexamethyleneiminomethyl-1-propenylsilane,
1-hexamethyleneiminomethyldi-n-propyl 1-propenylsilane,
Diethyl-2- (1-hexamethyleneimino) ethyl-1-propenylsilane,
2- (1-hexamethyleneimino) ethyldi-n-propyl 1-propenylsilane,
Diethyl-3- (1-hexamethyleneimino) -n-propyl 1-propenylsilane,
3- (1-hexamethyleneimino) -n-propyldi-n-propyl1-propenylsilane,

1-heptamethyleneiminomethyldimethyl-1-propenylsilane, 2- (1-heptamethyleneimino) ethyldimethyl-1-propenylsilane, 3- (1-heptamethyleneimino) -n-propyldimethyl-1-propenylsilane,
Diethyl-1-heptamethyleneiminomethyl-1-propenylsilane,
1-heptamethyleneiminomethyldi-n-propyl 1-propenylsilane,
Diethyl-2- (1-heptamethyleneimino) ethyl-1-propenylsilane,
2- (1-heptamethyleneimino) ethyldi-n-propyl 1-propenylsilane,
Diethyl-3- (1-heptamethyleneimino) -n-propyl 1-propenylsilane,
3- (1-heptamethyleneimino) -n-propyldi-n-propyl1-propenylsilane,

Dimethyl-1-octamethyleneiminomethyl-1-propenylsilane, dimethyl-2- (1-octamethyleneimino) ethyl-1-propenylsilane, dimethyl-3- (1-octamethyleneimino) -n-propyl-1-propenyl Silane,
Diethyl-1-octamethyleneiminomethyl-1-propenylsilane,
1-octamethyleneiminomethyldi-n-propyl 1-propenylsilane,
Diethyl-2- (1-octamethyleneimino) ethyl-1-propenylsilane,
2- (1-octamethyleneimino) ethyldi-n-propyl 1-propenylsilane,
Diethyl-3- (1-octamethyleneimino) -n-propyl 1-propenylsilane,
3- (1-octamethyleneimino) -n-propyldi-n-propyl1-propenylsilane,

1-decamethyleneiminomethyldimethyl-1-propenylsilane, 2- (1-decamethyleneimino) ethyldimethyl-1-propenylsilane, 3- (1-decamethyleneimino) -n-propyldimethyl-1-propenylsilane,
1-decamethyleneiminomethyldiethyl-1-propenylsilane,
1-decamethyleneiminomethyldi-n-propyl 1-propenylsilane,
2- (1-decamethyleneimino) ethyldiethyl-1-propenylsilane,
2- (1-decamethyleneimino) ethyldi-n-propyl 1-propenylsilane,
3- (1-decamethyleneimino) -n-propyldiethyl-1-propenylsilane,
3- (1-Decamethyleneimino) -n-propyldi-n-propyl1-propenylsilane,

1-dodecamethyleneiminomethyldimethyl-1-propenylsilane, 2- (1-dodecamethyleneimino) ethyldimethyl-1-propenylsilane, 3- (1-dodecamethyleneimino) -n-propyldimethyl-1-propenylsilane,
1-dodecamethyleneiminomethyldiethyl-1-propenylsilane,
1-dodecamethyleneiminomethyldi-n-propyl 1-propenylsilane,
2- (1-dodecamethyleneimino) ethyldiethyl-1-propenylsilane,
2- (1-dodecamethyleneimino) ethyldi-n-propyl 1-propenylsilane,
3- (1-dodecamethyleneimino) -n-propyldiethyl-1-propenylsilane,
3- (1-dodecamethyleneimino) -n-propyldi-n-propyl 1-propenylsilane.

[10] 1-polymethyleneiminoalkyldialkylisopropenylsilane:
1-aziridinylmethyldimethylisopropenylsilane, 2- (1-aziridinyl) ethyldimethylisopropenylsilane, 3- (1-aziridinyl) -n-propyldimethylisopropenylsilane,
1-aziridinylmethyldiethylisopropenylsilane,
1-aziridinylmethyldi-n-propylisopropenylsilane,
2- (1-aziridinyl) ethyldiethylisopropenylsilane,
2- (1-aziridinyl) ethyldi-n-propylisopropenylsilane,
3- (1-aziridinyl) -n-propyldiethylisopropenylsilane,
3- (1-aziridinyl) -n-propyldi-n-propylisopropenylsilane,

1-azeridinylmethyldimethylisopropenylsilane, 2- (1-azeridinyl) ethyldimethylisopropenylsilane, 3- (1-azeridinyl) -n-propyldimethylisopropenylsilane,
1-azeridinylmethyldiethylisopropenylsilane,
1-azeridinylmethyldi-n-propylisopropenylsilane,
2- (1-azeridinyl) ethyldiethylisopropenylsilane,
2- (1-azelidinyl) ethyldi-n-propylisopropenylsilane,
3- (1-azelidinyl) -n-propyldiethylisopropenylsilane,
3- (1-azelidinyl) -n-propyldi-n-propylisopropenylsilane,

Dimethyl-1-pyrrolidinylmethylisopropenylsilane, dimethyl-2- (1-pyrrolidinyl) ethylisopropenylsilane, 3dimethyl- (1-pyrrolidinyl) -n-propylisopropenylsilane,
Diethyl-1-pyrrolidinylmethylisopropenylsilane,
1-pyrrolidinylmethyldi-n-propylisopropenylsilane,
Diethyl-2- (1-pyrrolidinyl) ethylisopropenylsilane,
2- (1-pyrrolidinyl) ethyldi-n-propylisopropenylsilane,
Diethyl-3- (1-pyrrolidinyl) -n-propylisopropenylsilane,
3- (1-pyrrolidinyl) -n-propyldi-n-propylisopropenylsilane,

Dimethyl-1-piperidinylmethylisopropenylsilane, dimethyl-2- (1-piperidinyl) ethylisopropenylsilane, dimethyl-3- (1-piperidinyl) -n-propylisopropenylsilane,
Diethyl-1-piperidinylmethylisopropenylsilane,
1-piperidinylmethyldi-n-propylisopropenylsilane,
2- (1-piperidinyl) ethyldiethylisopropenylsilane,
2- (1-piperidinyl) ethyldi-n-propylisopropenylsilane,
Diethyl-3- (1-piperidinyl) -n-propylisopropenylsilane,
3- (1-piperidinyl) -n-propyldi-n-propylisopropenylsilane,

1-hexamethyleneiminomethyldimethylisopropenylsilane, 2- (1-hexamethyleneimino) ethyldimethylisopropenylsilane, 3- (1-hexamethyleneimino) -n-propyldimethylisopropenylsilane,
Diethyl-1-hexamethyleneiminomethylisopropenylsilane,
1-hexamethyleneiminomethyldi-n-propylisopropenylsilane,
Diethyl-2- (1-hexamethyleneimino) ethylisopropenylsilane,
2- (1-hexamethyleneimino) ethyldi-n-propylisopropenylsilane,
Diethyl-3- (1-hexamethyleneimino) -n-propylisopropenylsilane,
3- (1-hexamethyleneimino) -n-propyldi-n-propylisopropenylsilane,

1-heptamethyleneiminomethyldimethylisopropenylsilane, 2- (1-heptamethyleneimino) ethyldimethylisopropenylsilane, 3- (1-heptamethyleneimino) -n-propyldimethylisopropenylsilane,
Diethyl-1-heptamethyleneiminomethylisopropenylsilane,
1-heptamethyleneiminomethyldi-n-propylisopropenylsilane,
Diethyl-2- (1-heptamethyleneimino) ethylisopropenylsilane,
2- (1-heptamethyleneimino) ethyldi-n-propylisopropenylsilane,
Diethyl-3- (1-heptamethyleneimino) -n-propylisopropenylsilane,
3- (1-heptamethyleneimino) -n-propyldi-n-propylisopropenylsilane,

Dimethyl-1-octamethyleneiminomethylisopropenylsilane, dimethyl-2- (1-octamethyleneimino) ethylisopropenylsilane, dimethyl-3- (1-octamethyleneimino) -n-propylisopropenylsilane,
Diethyl-1-octamethyleneiminomethylisopropenylsilane,
1-octamethyleneiminomethyldi-n-propylisopropenylsilane,
Diethyl-2- (1-octamethyleneimino) ethylisopropenylsilane,
2- (1-octamethyleneimino) ethyldi-n-propylisopropenylsilane,
Diethyl-3- (1-octamethyleneimino) -n-propylisopropenylsilane,
3- (1-octamethyleneimino) -n-propyldi-n-propylisopropenylsilane,

1-decamethyleneiminomethyldimethylisopropenylsilane, 2- (1-decamethyleneimino) ethyldimethylisopropenylsilane, 3- (1-decamethyleneimino) -n-propyldimethylisopropenylsilane,
1-decamethyleneiminomethyldiethylisopropenylsilane,
1-decamethyleneiminomethyldi-n-propylisopropenylsilane,
2- (1-decamethyleneimino) ethyldiethylisopropenylsilane,
2- (1-decamethyleneimino) ethyldi-n-propylisopropenylsilane,
3- (1-decamethyleneimino) -n-propyldiethylisopropenylsilane,
3- (1-decamethyleneimino) -n-propyldi-n-propylisopropenylsilane,

1-dodecamethyleneiminomethyldimethylisopropenylsilane, 2- (1-dodecamethyleneimino) ethyldimethylisopropenylsilane, 3- (1-dodecamethyleneimino) -n-propyldimethylisopropenylsilane,
1-dodecamethyleneiminomethyldiethylisopropenylsilane,
1-dodecamethyleneiminomethyldi-n-propylisopropenylsilane,
2- (1-dodecamethyleneimino) ethyldiethylisopropenylsilane,
2- (1-dodecamethyleneimino) ethyldi-n-propylisopropenylsilane,
3- (1-dodecamethyleneimino) -n-propyldiethylisopropenylsilane,
3- (1-dodecamethyleneimino) -n-propyldi-n-propylisopropenylsilane.

[11] 1-polymethyleneiminoalkyldialkylcrotylsilane:
1-aziridinylmethyldimethylcrotylsilane, 2- (1-aziridinyl) ethyldimethylcrotylsilane, 3- (1-aziridinyl) -n-propyldimethylcrotylsilane,
1-aziridinylmethyldiethylcrotylsilane,
1-aziridinylmethyldi-n-propylcrotylsilane,
2- (1-aziridinyl) ethyldiethylcrotylsilane,
2- (1-aziridinyl) ethyldi-n-propylcrotylsilane,
3- (1-aziridinyl) -n-propyldiethylcrotylsilane,
3- (1-aziridinyl) -n-propyldi-n-propylcrotylsilane,

1-azeridinylmethyldimethylcrotylsilane, 2- (1-azelidinyl) ethyldimethylcrotylsilane, 3- (1-azelidinyl) -n-propyldimethylcrotylsilane,
1-azeridinylmethyldiethylcrotylsilane,
1-azeridinylmethyldi-n-propylcrotylsilane,
2- (1-azeridinyl) ethyldiethylcrotylsilane,
2- (1-azeridinyl) ethyldi-n-propylcrotylsilane,
3- (1-azelidinyl) -n-propyldiethylcrotylsilane,
3- (1-azelidinyl) -n-propyldi-n-propylcrotylsilane,

Dimethyl-1-pyrrolidinylmethylcrotylsilane, dimethyl-2- (1-pyrrolidinyl) ethylcrotylsilane, 3dimethyl- (1-pyrrolidinyl) -n-propylcrotylsilane,
Diethyl-1-pyrrolidinylmethylcrotylsilane,
1-pyrrolidinylmethyldi-n-propylcrotylsilane,
Diethyl-2- (1-pyrrolidinyl) ethylcrotylsilane,
2- (1-pyrrolidinyl) ethyldi-n-propylcrotylsilane,
Diethyl-3- (1-pyrrolidinyl) -n-propylcrotylsilane,
3- (1-pyrrolidinyl) -n-propyldi-n-propylcrotylsilane,

Dimethyl-1-piperidinylmethylcrotylsilane, dimethyl-2- (1-piperidinyl) ethylcrotylsilane, dimethyl-3- (1-piperidinyl) -n-propylcrotylsilane,
Diethyl-1-piperidinylmethylcrotylsilane,
1-piperidinylmethyldi-n-propylcrotylsilane,
2- (1-piperidinyl) ethyldiethylcrotylsilane,
2- (1-piperidinyl) ethyldi-n-propylcrotylsilane,
Diethyl-3- (1-piperidinyl) -n-propylcrotylsilane,
3- (1-piperidinyl) -n-propyldi-n-propylcrotylsilane,

1-hexamethyleneiminomethyldimethylcrotylsilane, 2- (1-hexamethyleneimino) ethyldimethylcrotylsilane, 3- (1-hexamethyleneimino) -n-propyldimethylcrotylsilane,
Diethyl-1-hexamethyleneiminomethylcrotylsilane,
1-hexamethyleneiminomethyldi-n-propylcrotylsilane,
Diethyl-2- (1-hexamethyleneimino) ethylcrotylsilane,
2- (1-hexamethyleneimino) ethyldi-n-propylcrotylsilane,
Diethyl-3- (1-hexamethyleneimino) -n-propylcrotylsilane,
3- (1-hexamethyleneimino) -n-propyldi-n-propylcrotylsilane,

1-heptamethyleneiminomethyldimethylcrotylsilane, 2- (1-heptamethyleneimino) ethyldimethylcrotylsilane, 3- (1-heptamethyleneimino) -n-propyldimethylcrotylsilane,
Diethyl-1-heptamethyleneiminomethylcrotylsilane,
1-heptamethyleneiminomethyldi-n-propylcrotylsilane,
Diethyl-2- (1-heptamethyleneimino) ethylcrotylsilane,
2- (1-heptamethyleneimino) ethyldi-n-propylcrotylsilane,
Diethyl-3- (1-heptamethyleneimino) -n-propylcrotylsilane,
3- (1-heptamethyleneimino) -n-propyldi-n-propylcrotylsilane,

Dimethyl-1-octamethyleneiminomethylcrotylsilane, dimethyl-2- (1-octamethyleneimino) ethylcrotylsilane, dimethyl-3- (1-octamethyleneimino) -n-propylcrotylsilane,
Diethyl-1-octamethyleneiminomethylcrotylsilane,
1-octamethyleneiminomethyldi-n-propylcrotylsilane,
Diethyl-2- (1-octamethyleneimino) ethylcrotylsilane,
2- (1-octamethyleneimino) ethyldi-n-propylcrotylsilane,
Diethyl-3- (1-octamethyleneimino) -n-propylcrotylsilane,
3- (1-octamethyleneimino) -n-propyldi-n-propylcrotylsilane,

1-decamethyleneiminomethyldimethylcrotylsilane, 2- (1-decamethyleneimino) ethyldimethylcrotylsilane, 3- (1-decamethyleneimino) -n-propyldimethylcrotylsilane,
1-decamethyleneiminomethyldiethylcrotylsilane,
1-decamethyleneiminomethyldi-n-propylcrotylsilane,
2- (1-decamethyleneimino) ethyldiethylcrotylsilane,
2- (1-decamethyleneimino) ethyldi-n-propylcrotylsilane,
3- (1-decamethyleneimino) -n-propyldiethylcrotylsilane,
3- (1-Decamethyleneimino) -n-propyldi-n-propylcrotylsilane,

1-dodecamethyleneiminomethyldimethylcrotylsilane, 2- (1-dodecamethyleneimino) ethyldimethylcrotylsilane, 3- (1-dodecamethyleneimino) -n-propyldimethylcrotylsilane,
1-dodecamethyleneiminomethyldiethylcrotylsilane,
1-dodecamethyleneiminomethyldi-n-propylcrotylsilane,
2- (1-dodecamethyleneimino) ethyldiethylcrotylsilane,
2- (1-dodecamethyleneimino) ethyldi-n-propylcrotylsilane,
3- (1-dodecamethyleneimino) -n-propyldiethylcrotylsilane,
3- (1-dodecamethyleneimino) -n-propyldi-n-propylcrotylsilane.

[12] 1-polymethyleneiminoalkyldialkylmethallylsilane:
1-aziridinylmethyldimethylmethallylsilane, 2- (1-aziridinyl) ethyldimethylmethallylsilane, 3- (1-aziridinyl) -n-propyldimethylmethallylsilane,
1-aziridinylmethyldiethylmethallylsilane,
1-aziridinylmethyldi-n-propylmethallylsilane,
2- (1-aziridinyl) ethyldiethylmethallylsilane,
2- (1-aziridinyl) ethyldi-n-propylmethallylsilane,
3- (1-aziridinyl) -n-propyldiethylmethallylsilane,
3- (1-aziridinyl) -n-propyldi-n-propylmethallylsilane,

1-azeridinylmethyldimethylmethallylsilane, 2- (1-azeridinyl) ethyldimethylmethallylsilane, 3- (1-azeridinyl) -n-propyldimethylmethallylsilane,
1-azeridinylmethyldiethylmethallylsilane,
1-azeridinylmethyldi-n-propylmethallylsilane,
2- (1-azelidinyl) ethyldiethylmethallylsilane,
2- (1-azeridinyl) ethyldi-n-propylmethallylsilane,
3- (1-azeridinyl) -n-propyldiethylmethallylsilane,
3- (1-azelidinyl) -n-propyldi-n-propylmethallylsilane,

Dimethyl-1-pyrrolidinylmethylmethallylsilane, dimethyl-2- (1-pyrrolidinyl) ethylmethallylsilane, 3dimethyl- (1-pyrrolidinyl) -n-propylmethallylsilane,
Diethyl-1-pyrrolidinylmethylmethallylsilane,
1-pyrrolidinylmethyldi-n-propylmethallylsilane,
Diethyl-2- (1-pyrrolidinyl) ethylmethallylsilane,
2- (1-pyrrolidinyl) ethyldi-n-propylmethallylsilane,
Diethyl-3- (1-pyrrolidinyl) -n-propylmethallylsilane,
3- (1-pyrrolidinyl) -n-propyldi-n-propylmethallylsilane,

Dimethyl-1-piperidinylmethylmethallylsilane, dimethyl-2- (1-piperidinyl) ethylmethallylsilane, dimethyl-3- (1-piperidinyl) -n-propylmethallylsilane,
Diethyl-1-piperidinylmethylmethallylsilane,
1-piperidinylmethyldi-n-propylmethallylsilane,
2- (1-piperidinyl) ethyldiethylmethallylsilane,
2- (1-piperidinyl) ethyldi-n-propylmethallylsilane,
Diethyl-3- (1-piperidinyl) -n-propylmethallylsilane,
3- (1-piperidinyl) -n-propyldi-n-propylmethallylsilane,

1-hexamethyleneiminomethyldimethylmethallylsilane, 2- (1-hexamethyleneimino) ethyldimethylmethallylsilane, 3- (1-hexamethyleneimino) -n-propyldimethylmethallylsilane,
Diethyl-1-hexamethyleneiminomethylmethallylsilane,
1-hexamethyleneiminomethyldi-n-propylmethallylsilane,
Diethyl-2- (1-hexamethyleneimino) ethylmethallylsilane,
2- (1-hexamethyleneimino) ethyldi-n-propylmethallylsilane,
Diethyl-3- (1-hexamethyleneimino) -n-propylmethallylsilane,
3- (1-hexamethyleneimino) -n-propyldi-n-propylmethallylsilane,

1-heptamethyleneiminomethyldimethylmethallylsilane, 2- (1-heptamethyleneimino) ethyldimethylmethallylsilane, 3- (1-heptamethyleneimino) -n-propyldimethylmethallylsilane,
Diethyl-1-heptamethyleneiminomethylmethallylsilane,
1-heptamethyleneiminomethyldi-n-propylmethallylsilane,
Diethyl-2- (1-heptamethyleneimino) ethylmethallylsilane,
2- (1-heptamethyleneimino) ethyldi-n-propylmethallylsilane,
Diethyl-3- (1-heptamethyleneimino) -n-propylmethallylsilane,
3- (1-heptamethyleneimino) -n-propyldi-n-propylmethallylsilane,

Dimethyl-1-octamethyleneiminomethylmethallylsilane, dimethyl-2- (1-octamethyleneimino) ethylmethallylsilane, dimethyl-3- (1-octamethyleneimino) -n-propylmethallylsilane,
Diethyl-1-octamethyleneiminomethylmethallylsilane,
1-octamethyleneiminomethyldi-n-propylmethallylsilane,
Diethyl-2- (1-octamethyleneimino) ethylmethallylsilane,
2- (1-octamethyleneimino) ethyldi-n-propylmethallylsilane,
Diethyl-3- (1-octamethyleneimino) -n-propylmethallylsilane,
3- (1-octamethyleneimino) -n-propyldi-n-propylmethallylsilane,

1-decamethyleneiminomethyldimethylmethallylsilane, 2- (1-decamethyleneimino) ethyldimethylmethallylsilane, 3- (1-decamethyleneimino) -n-propyldimethylmethallylsilane,
1-decamethyleneiminomethyldiethylmethallylsilane,
1-decamethyleneiminomethyldi-n-propylmethallylsilane,
2- (1-decamethyleneimino) ethyldiethylmethallylsilane,
2- (1-decamethyleneimino) ethyldi-n-propylmethallylsilane,
3- (1-decamethyleneimino) -n-propyldiethylmethallylsilane,
3- (1-Decamethyleneimino) -n-propyldi-n-propylmethallylsilane,

1-dodecamethyleneiminomethyldimethylmethallylsilane, 2- (1-dodecamethyleneimino) ethyldimethylmethallylsilane, 3- (1-dodecamethyleneimino) -n-propyldimethylmethallylsilane,
1-dodecamethyleneiminomethyldiethylmethallylsilane,
1-dodecamethyleneiminomethyldi-n-propylmethallylsilane,
2- (1-dodecamethyleneimino) ethyldiethylmethallylsilane,
2- (1-dodecamethyleneimino) ethyldi-n-propylmethallylsilane,
3- (1-dodecamethyleneimino) -n-propyldiethylmethallylsilane,
3- (1-dodecamethyleneimino) -n-propyldi-n-propylmethallylsilane.

As the compound represented by the formula (41), R ⁴⁰¹ is a group represented by the formula (42), m ⁴ is 2, and A ⁴⁰¹ is a non-cyclic amino group represented by the formula (43). There are certain compounds.
As the compound,
Bis (dialkylamino) alkylalkylvinylsilane,
Bis (dialkylamino) alkylalkylallylsilane,
Bis (dialkylamino) alkylalkyl-1-propenylsilane,
Bis (dialkylamino) alkylalkylisopropenylsilane.
Specific compounds will be exemplified in the following paragraphs.

[13] Bis (dialkylamino) alkylalkylvinylsilane:
Bis (dimethylamino) methylmethylvinylsilane, bis (diethylamino) methylmethylvinylsilane, bis (di-n-propylamino) methylmethylvinylsilane, bis (dimethylamino) methylethylvinylsilane, bis (diethylamino) methylethylvinylsilane, bis (di -N-propylamino) methylethylvinylsilane,

2-bis (dimethylamino) ethylmethylvinylsilane, 2-bis (diethylamino) ethylmethylvinylsilane, 2-bis (di-n-propylamino) ethylmethylvinylsilane, 2-bis (dimethylamino) ethylethylvinylsilane, 2-bis (Diethylamino) ethylethylvinylsilane, 2-bis (di-n-propylamino) ethylethylvinylsilane,

3-bis (dimethylamino) -n-propylmethylvinylsilane, 3-bis (diethylamino) -n-propylmethylvinylsilane, 3-bis (di-n-propylamino) -n-propylmethylvinylsilane, 3-bis (dimethyl) Amino) -n-propylethylvinylsilane, 3-bis (diethylamino) -n-propylethylvinylsilane, 3-bis (di-n-propylamino) -n-propylethylvinylsilane.

[14] Bis (dialkylamino) alkylalkylallylsilane:
Bis (dimethylamino) methylmethylallylsilane, bis (diethylamino) methylmethylallylsilane, bis (di-n-propylamino) methylmethylallylsilane, bis (dimethylamino) methylethylallylsilane, bis (diethylamino) methylethylallylsilane, bis (di -N-propylamino) methylethylallylsilane,

2-bis (dimethylamino) ethylmethylallylsilane, 2-bis (diethylamino) ethylmethylallylsilane, 2-bis (di-n-propylamino) ethylmethylallylsilane, 2-bis (dimethylamino) ethylethylallylsilane, 2-bis (Diethylamino) ethylethylallylsilane, 2-bis (di-n-propylamino) ethylethylallylsilane,

3-bis (dimethylamino) -n-propylmethylallylsilane, 3-bis (diethylamino) -n-propylmethylallylsilane, 3-bis (di-n-propylamino) -n-propylmethylallylsilane, 3-bis (dimethyl) Amino) -n-propylethylallylsilane, 3-bis (diethylamino) -n-propylethylallylsilane, 3-bis (di-n-propylamino) -n-propylethylallylsilane.

[15] Bis (dialkylamino) alkylalkyl-1-propenylsilane:
Bis (dimethylamino) methylmethyl-1-propenylsilane, bis (diethylamino) methylmethyl-1-propenylsilane, bis (di-n-propylamino) methylmethyl-1-propenylsilane, bis (dimethylamino) methylethyl- 1-propenylsilane, bis (diethylamino) methylethyl-1-propenylsilane, bis (di-n-propylamino) methylethyl-1-propenylsilane,

2-bis (dimethylamino) ethylmethyl-1-propenylsilane, 2-bis (diethylamino) ethylmethyl-1-propenylsilane, 2-bis (di-n-propylamino) ethylmethyl-1-propenylsilane, 2- Bis (dimethylamino) ethylethyl-1-propenylsilane, 2-bis (diethylamino) ethylethyl-1-propenylsilane, 2-bis (di-n-propylamino) ethylethyl-1-propenylsilane,

3-bis (dimethylamino) -n-propylmethyl-1-propenylsilane, 3-bis (diethylamino) -n-propylmethyl-1-propenylsilane, 3-bis (di-n-propylamino) -n-propyl Methyl-1-propenylsilane, 3-bis (dimethylamino) -n-propylethyl-1-propenylsilane, 3-bis (diethylamino) -n-propylethyl-1-propenylsilane, 3-bis (di-n- Propylamino) -n-propylethyl-1-propenylsilane.

[16] Bis (dialkylamino) alkylalkylisopropenylsilane:
Bis (dimethylamino) methylmethylisopropenylsilane, bis (diethylamino) methylmethylisopropenylsilane, bis (di-n-propylamino) methylmethylisopropenylsilane, bis (dimethylamino) methylethylisopropenylsilane, bis (diethylamino) ) Methyl ethyl isopropenyl silane, bis (di-n-propylamino) methyl ethyl isopropenyl silane,

2-bis (dimethylamino) ethylmethylisopropenylsilane, 2-bis (diethylamino) ethylmethylisopropenylsilane, 2-bis (di-n-propylamino) ethylmethylisopropenylsilane, 2-bis (dimethylamino) ethyl Ethylisopropenylsilane, 2-bis (diethylamino) ethylethylisopropenylsilane, 2-bis (di-n-propylamino) ethylethylisopropenylsilane,

3-bis (dimethylamino) -n-propylmethylisopropenylsilane, 3-bis (diethylamino) -n-propylmethylisopropenylsilane, 3-bis (di-n-propylamino) -n-propylmethylisopropenylsilane 3-bis (dimethylamino) -n-propylethylisopropenylsilane, 3-bis (diethylamino) -n-propylethylisopropenylsilane, 3-bis (di-n-propylamino) -n-propylethylisopropenyl Silane.

As a compound represented by the formula (41), R ⁴⁰¹ is a group represented by the formula (42), m ⁴ is 2, and A ⁴⁰¹ is a cyclic amino group represented by the formula (43). Compounds.
As the compound,
Di (1-polymethyleneimino) alkylalkylvinylsilane,
Di (1-polymethyleneimino) alkylalkylallylsilane,
Di (1-polymethyleneimino) alkylalkyl-1-propenylsilane,
Examples include di (1-polymethyleneimino) alkylalkylisopropenylsilane.
Specific compounds will be exemplified in the following paragraphs.

[17] Di (1-polymethyleneimino) alkylalkylvinylsilane:
Di (1-pyrrolidinyl) methylmethylvinylsilane, 2,2′-di (1-pyrrolidinyl) ethylmethylvinylsilane, 3,3′-di (1-pyrrolidinyl) -n-propylmethylvinylsilane,
2-di (1-pyrrolidinyl) ethylethylvinylsilane,
2-di (1-pyrrolidinyl) ethyl-n-propylvinylsilane,
3-di (1-pyrrolidinyl) -n-propylethylvinylsilane,
3-di (1-pyrrolidinyl) -n-propyl n-propylvinylsilane,

Di (1-piperidinyl) methylmethylvinylsilane, 2,2′-di (1-piperidinyl) ethylmethylvinylsilane, 3,3′-di (1-piperidinyl) -n-propylmethylvinylsilane,
2-di (1-piperidinyl) ethylethylvinylsilane,
2-di (1-piperidinyl) ethyl-n-propylvinylsilane,
3-di (1-piperidinyl) -n-propylethylvinylsilane,
3-di (1-piperidinyl) -n-propyl n-propylvinylsilane,

Di (1-hexamethyleneimino) methylmethylvinylsilane, 2,2′-di (1-hexamethyleneimino) ethylmethylvinylsilane, 3,3′-di (1-hexamethyleneimino) -n-propylmethylvinylsilane,
2-di (1-hexamethyleneimino) ethylethylvinylsilane,
2-di (1-hexamethyleneimino) ethyl-n-propylvinylsilane,
3-di (1-hexamethyleneimino) -n-propylethylvinylsilane,
3-di (1-hexamethyleneimino) -n-propyl n-propylvinylsilane,

Di (1-heptamethyleneimino) methylmethylvinylsilane, 2,2′-di (1-heptamethyleneimino) ethylmethylvinylsilane, 3,3′-di (1-heptamethyleneimino) -n-propylmethylvinylsilane,
2-di (1-heptamethyleneimino) ethylethylvinylsilane,
2-di (1-heptamethyleneimino) ethyl-n-propylvinylsilane,
3-di (1-heptamethyleneimino) -n-propylethylvinylsilane,
3-di (1-heptamethyleneimino) -n-propyl n-propylvinylsilane.

[18] Di (1-polymethyleneimino) alkylalkylallylsilane:
Di (1-pyrrolidinyl) methylmethylallylsilane, 2,2′-di (1-pyrrolidinyl) ethylmethylallylsilane, 3,3′-di (1-pyrrolidinyl) -n-propylmethylallylsilane,
2-di (1-pyrrolidinyl) ethylethylallylsilane,
2-di (1-pyrrolidinyl) ethyl-n-propylallylsilane,
3-di (1-pyrrolidinyl) -n-propylethylallylsilane,
3-di (1-pyrrolidinyl) -n-propyl n-propylallylsilane,

Di (1-piperidinyl) methylmethylallylsilane, 2,2′-di (1-piperidinyl) ethylmethylallylsilane, 3,3′-di (1-piperidinyl) -n-propylmethylallylsilane,
2-di (1-piperidinyl) ethylethylallylsilane,
2-di (1-piperidinyl) ethyl-n-propylallylsilane,
3-di (1-piperidinyl) -n-propylethylallylsilane,
3-di (1-piperidinyl) -n-propyl n-propylallylsilane,

Di (1-hexamethyleneimino) methylmethylallylsilane, 2,2′-di (1-hexamethyleneimino) ethylmethylallylsilane, 3,3′-di (1-hexamethyleneimino) -n-propylmethylallylsilane,
2-di (1-hexamethyleneimino) ethylethylallylsilane,
2-di (1-hexamethyleneimino) ethyl-n-propylallylsilane,
3-di (1-hexamethyleneimino) -n-propylethylallylsilane,
3-di (1-hexamethyleneimino) -n-propyl n-propylallylsilane,

Di (1-heptamethyleneimino) methylmethylallylsilane, 2,2′-di (1-heptamethyleneimino) ethylmethylallylsilane, 3,3′-di (1-heptamethyleneimino) -n-propylmethylallylsilane,
2-di (1-heptamethyleneimino) ethylethylallylsilane,
2-di (1-heptamethyleneimino) ethyl-n-propylallylsilane,
3-di (1-heptamethyleneimino) -n-propylethylallylsilane,
3-di (1-heptamethyleneimino) -n-propyl n-propylallylsilane.

[19] Di (1-polymethyleneimino) alkylalkyl-1-propenylsilane:
Di (1-pyrrolidinyl) methylmethyl-1-propenylsilane, 2,2′-di (1-pyrrolidinyl) ethylmethyl-1-propenylsilane, 3,3′-di (1-pyrrolidinyl) -n-propylmethyl- 1-propenylsilane,
2-di (1-pyrrolidinyl) ethylethyl-1-propenylsilane,
2-di (1-pyrrolidinyl) ethyl-n-propyl 1-propenylsilane,
3-di (1-pyrrolidinyl) -n-propylethyl-1-propenylsilane,
3-di (1-pyrrolidinyl) -n-propyl n-propyl 1-propenylsilane,

Di (1-piperidinyl) methylmethyl-1-propenylsilane, 2,2′-di (1-piperidinyl) ethylmethyl-1-propenylsilane, 3,3′-di (1-piperidinyl) -n-propylmethyl- 1-propenylsilane,
2-di (1-piperidinyl) ethylethyl-1-propenylsilane,
2-di (1-piperidinyl) ethyl-n-propyl 1-propenylsilane,
3-di (1-piperidinyl) -n-propylethyl-1-propenylsilane,
3-di (1-piperidinyl) -n-propyl n-propyl 1-propenylsilane,

Di (1-hexamethyleneimino) methylmethyl-1-propenylsilane, 2,2′-di (1-hexamethyleneimino) ethylmethyl-1-propenylsilane, 3,3′-di (1-hexamethyleneimino) -N-propylmethyl-1-propenylsilane,
2-di (1-hexamethyleneimino) ethylethyl-1-propenylsilane,
2-di (1-hexamethyleneimino) ethyl-n-propyl 1-propenylsilane,
3-di (1-hexamethyleneimino) -n-propylethyl-1-propenylsilane,
3-di (1-hexamethyleneimino) -n-propyl n-propyl 1-propenylsilane,

Di (1-heptamethyleneimino) methylmethyl-1-propenylsilane, 2,2′-di (1-heptamethyleneimino) ethylmethyl-1-propenylsilane, 3,3′-di (1-heptamethyleneimino) -N-propylmethyl-1-propenylsilane,
2-di (1-heptamethyleneimino) ethylethyl-1-propenylsilane,
2-di (1-heptamethyleneimino) ethyl-n-propyl 1-propenylsilane,
3-di (1-heptamethyleneimino) -n-propylethyl-1-propenylsilane,
3-di (1-heptamethyleneimino) -n-propyl n-propyl 1-propenylsilane.

[20] Di (1-polymethyleneimino) alkylalkylisopropenylsilane:
Di (1-pyrrolidinyl) methylmethylisopropenylsilane, 2,2′-di (1-pyrrolidinyl) ethylmethylisopropenylsilane, 3,3′-di (1-pyrrolidinyl) -n-propylmethylisopropenylsilane,
2-di (1-pyrrolidinyl) ethylethylisopropenylsilane,
2-di (1-pyrrolidinyl) ethyl-n-propylisopropenylsilane,
3-di (1-pyrrolidinyl) -n-propylethylisopropenylsilane,
3-di (1-pyrrolidinyl) -n-propyl n-propylisopropenylsilane,

Di (1-piperidinyl) methylmethylisopropenylsilane, 2,2′-di (1-piperidinyl) ethylmethylisopropenylsilane, 3,3′-di (1-piperidinyl) -n-propylmethylisopropenylsilane,
2-di (1-piperidinyl) ethylethylisopropenylsilane,
2-di (1-piperidinyl) ethyl-n-propylisopropenylsilane,
3-di (1-piperidinyl) -n-propylethylisopropenylsilane,
3-di (1-piperidinyl) -n-propyl n-propylisopropenylsilane,

Di (1-hexamethyleneimino) methylmethylisopropenylsilane, 2,2′-di (1-hexamethyleneimino) ethylmethylisopropenylsilane, 3,3′-di (1-hexamethyleneimino) -n-propyl Methyl isopropenyl silane,
2-di (1-hexamethyleneimino) ethylethylisopropenylsilane,
2-di (1-hexamethyleneimino) ethyl-n-propylisopropenylsilane,
3-di (1-hexamethyleneimino) -n-propylethylisopropenylsilane,
3-di (1-hexamethyleneimino) -n-propyl n-propylisopropenylsilane,

Di (1-heptamethyleneimino) methylmethylisopropenylsilane, 2,2′-di (1-heptamethyleneimino) ethylmethylisopropenylsilane, 3,3′-di (1-heptamethyleneimino) -n-propyl Methyl isopropenyl silane,
2-di (1-heptamethyleneimino) ethylethylisopropenylsilane,
2-di (1-heptamethyleneimino) ethyl-n-propylisopropenylsilane,
3-di (1-heptamethyleneimino) -n-propylethylisopropenylsilane,
3-di (1-heptamethyleneimino) -n-propyl n-propylisopropenylsilane.

As a compound represented by the formula (41), R ⁴⁰¹ is a group represented by the formula (42), m ⁴ is 3, and A ⁴⁰¹ is a substituted amino group represented by the formula (43). Compounds.
As the compound,
Tri (dialkylamino) alkylvinylsilane,
Examples include tri (1-polymethyleneimino) alkylvinylsilane.

[21] Tri (dialkylamino) alkylvinylsilane:
Tri (dimethylamino) methylvinylsilane, tri (diethylamino) methylvinylsilane, 2,2 ′, 2 ″ -tri (dimethylamino) ethylvinylsilane, 2,2 ′, 2 ″ -tri (diethylamino) ethylvinylsilane.

[22] Tri (1-polymethyleneimino) alkylvinylsilane:
Tri (1-pyrrolidinyl) methylvinylsilane, tri (1-pyrrolidinyl) methylvinylsilane, 2,2 ′, 2 ″ -tri (1-pyrrolidinyl) ethylvinylsilane, 2,2 ′, 2 ″ -tri (1-pyrrolidinyl) ) Ethyl vinyl silane.

As the compound represented by the formula (41), m ⁴ is preferably 1, R ⁴⁰¹ is a group represented by the formula (42), R ⁴⁰² is an alkylene group, and R ⁴⁰³ is an alkyl group. More preferably, m ⁴ is 1, R ⁴⁰¹ is a group represented by the formula (42), R ⁴⁰² is an alkylene group, R ⁴⁰³ is an alkyl group, and A ⁴⁰¹ Is a compound represented by the formula (43), and (dialkylamino) alkyldialkylvinylsilane and 1-polymethyleneiminoalkyldialkylvinylsilane are more preferable. (Dialkylamino) alkyldialkylvinylsilane is preferably dimethyl (dimethylaminomethyl) vinylsilane, and 1-polymethyleneiminoalkyldialkylvinylsilane is dimethyl-1-piperidinylmethylvinylsilane.

The compound represented by the formula (41) is particularly preferably 1-polymethyleneiminoalkyldialkylvinylsilane.

The content of the structural unit based on the monomer represented by the formula (41) in the conjugated diene polymer (D) is preferably 0.001 mmol per unit weight of the polymer in order to increase the wear resistance. / G polymer or more, more preferably 0.002 mmol / g polymer or more, and still more preferably 0.003 mmol / g polymer or more. Moreover, it is preferably 0.1 mmol / g polymer or less, more preferably 0.07 mmol / g polymer or less, and still more preferably 0.05 mmol / g polymer or less.

The conjugated diene polymer (D) preferably has an aromatic vinyl unit in order to increase the strength. As the content of the aromatic vinyl unit, the total amount of the conjugated diene unit and the aromatic vinyl unit is 100% by mass, preferably 10% by mass or more (the content of the conjugated diene unit is 90% by mass or less), and more Preferably it is 15 mass% or more (content of a conjugated diene unit is 85 mass% or less). In order to improve fuel economy, the content of the aromatic vinyl unit is preferably 50% by mass or less (the content of the conjugated diene unit is 50% by mass or more), more preferably 45% by mass or less (conjugated). The diene unit content is 55% by mass or more).

The vinyl bond content of the conjugated diene polymer (D) is preferably 80 mol% or less, more preferably 70 mol% or less in order to improve fuel efficiency, with the content of the conjugated diene unit being 100 mol%. It is. Moreover, in order to improve grip property, Preferably it is 10 mol% or more, More preferably, it is 15 mol% or more, More preferably, it is 20 mol% or more, Most preferably, it is 40 mol% or more. The vinyl bond amount is determined from the absorption intensity in the vicinity of 910 cm ^−1, which is the absorption peak of the vinyl group, by infrared spectroscopy.

The Mooney viscosity (ML _{1 + 4} ) of the conjugated diene polymer (D) is preferably 10 or more, more preferably 20 or more, in order to increase the strength. Moreover, in order to improve workability, Preferably it is 200 or less, More preferably, it is 150 or less. The Mooney viscosity (ML _{1 + 4} ) is measured at 100 ° C. according to JIS K6300 (1994).

The molecular weight distribution of the conjugated diene polymer (D) is preferably 1 to 5 and more preferably 1 to 3 in order to improve fuel efficiency. The molecular weight distribution is obtained by measuring the number average molecular weight (Mn) and the weight average molecular weight (Mw) by gel permeation chromatography (GPC) method and dividing Mw by Mn.

[Production Method of Conjugated Diene Polymer (D)]
A suitable method for producing the conjugated diene polymer (D) is a method in which a monomer containing a conjugated diene and a compound represented by the formula (41) is polymerized with an alkali metal catalyst in a hydrocarbon solvent. . For example, the following method A ⁴ , method B ⁴ and method C ⁴ can be mentioned.

<Method A ⁴ >
The manufacturing method which has the following process (a1-4) and (a2-4).
Step (a1-4): A step of preparing a reaction product of the alkali metal catalyst and the compound by bringing the alkali metal catalyst and the compound represented by the formula (41) into contact with each other in a hydrocarbon solvent.
Step (a2-4): A step of polymerizing a monomer containing a conjugated diene in a hydrocarbon solvent using the reaction product prepared in step (a1-4) as a polymerization initiator.

<Method B ⁴ >
The manufacturing method which has the following process (b1-4).
Step (b1-4): A step of copolymerizing a monomer containing a conjugated diene and a compound represented by the formula (41) with an alkali metal catalyst in a hydrocarbon solvent.

<Method C ⁴ >
The manufacturing method which has the following process (c1-4) and (c2-4).
Step (c1-4): In a hydrocarbon solvent, a monomer containing a conjugated diene is polymerized with an alkali metal catalyst, and at least one terminal of a polymer chain having a monomer unit based on the conjugated diene, A step of obtaining a polymer having an alkali metal derived from a catalyst.
Step (c2-4): A step of reacting the compound represented by the formula (41) with the polymer terminal having an alkali metal of the polymer obtained in the step (c1-4).

In the method A ^4, as a monomer of step (a2-4), in addition to the conjugated diene, may be used a compound represented by the formula (41), also with other monomers described later Good. Moreover, you may provide the process (process (a3-4)) with which the compound represented by Formula (41) is made to react with the polymer terminal which has the alkali metal of the polymer obtained at the process (a2-4). .

In the method B ^4, as a monomer in step (b1-4), in addition to the compound represented by the conjugated diene and (41) may be used other monomers described later. Moreover, you may provide the process (process (b2-4)) with which the compound represented by Formula (41) is made to react with the polymer terminal which has the alkali metal of the polymer obtained at the process (b1-4). .

In the method C ^4, as a monomer of step (C1-4), in addition to the conjugated diene, it may be used a compound represented by the formula (41), also with other monomers described later Good.

Examples of the alkali metal catalyst include alkali metals, organic alkali metal compounds, complexes of alkali metals and polar compounds, and oligomers having alkali metals.

Examples of the alkali metal include lithium, sodium, potassium, rubidium, and cesium.

Examples of the organic alkali metal compound include ethyl lithium, n-propyl lithium, iso-propyl lithium, n-butyl lithium, sec-butyl lithium, t-octyl lithium, n-decyl lithium, phenyl lithium, 2-naphthyl lithium, 2- Butylphenyllithium, 4-phenylbutyllithium, cyclohexyllithium, 4-cyclopentyllithium, dimethylaminopropyllithium, diethylaminopropyllithium, t-butyldimethylsiloxypropyllithium, N-morpholinopropyllithium, lithium hexamethyleneimide, lithium pyrrolidide , Lithium piperidide, lithium heptamethylene imide, lithium dodecamethylene imide, 1,4-dilithio-2-butene, sodium naphthalenide, sodium Fenirido, potassium naphthalenide the like.

Examples of the complex of an alkali metal and a polar compound include a potassium-tetrahydrofuran complex and a potassium-diethoxyethane complex.

Examples of the oligomer having an alkali metal include sodium salt of α-methylstyrene tetramer.

The alkali metal catalyst is preferably an organic lithium compound or an organic sodium compound, and more preferably an organic lithium compound or an organic sodium compound having 2 to 20 carbon atoms.

The hydrocarbon solvent used in the above production method is a solvent that does not deactivate the organic alkali metal compound catalyst, and examples thereof include aliphatic hydrocarbons, aromatic hydrocarbons, and alicyclic hydrocarbons. Aliphatic hydrocarbons include propane, n-butane, iso-butane, n-pentane, iso-pentane, n-hexane, propene, 1-butene, iso-butene, trans-2-butene, cis-2-butene 1-pentene, 2-pentene, 1-hexene and 2-hexene. Aromatic hydrocarbons include benzene, toluene, xylene, and ethylbenzene. Examples of the alicyclic hydrocarbon include cyclopentane and cyclohexane. One or more of these may be used, and the hydrocarbon solvent may be a mixture of various components such as industrial hexane. The hydrocarbon solvent is preferably a hydrocarbon having 2 to 12 carbon atoms.

Examples of the conjugated diene used in the above production method include 1,3-butadiene, isoprene, 1,3-pentadiene, 2,3-dimethyl-1,3-butadiene, and 1,3-hexadiene. One or more of these are used. The conjugated diene is preferably 1,3-butadiene or isoprene.

Examples of the other monomer used in the step (a2-4), the step (b1-4) and the step (c1-4) include aromatic vinyl, vinyl nitrile, and unsaturated carboxylic acid ester. Examples of the aromatic vinyl include styrene, α-methylstyrene, vinyl toluene, vinyl naphthalene, divinyl benzene, trivinyl benzene, and divinyl naphthalene. Examples of the vinyl nitrile include acrylonitrile, and examples of the unsaturated carboxylic acid ester include methyl acrylate, ethyl acrylate, methyl methacrylate, and ethyl methacrylate. Aromatic vinyl is preferable, and styrene is more preferable.

In the polymerization step of the above production method, an agent for adjusting the vinyl bond amount of the conjugated diene unit and / or a distribution of constituent units based on monomers other than the conjugated diene unit and the conjugated diene in the conjugated diene polymer chain May be carried out in the presence of an agent that adjusts (hereinafter collectively referred to as “regulator”). Examples of such a regulator include ether compounds, tertiary amines, and phosphine compounds. Examples of ether compounds include cyclic ethers such as tetrahydrofuran, tetrahydropyran, and 1,4-dioxane; aliphatic monoethers such as diethyl ether and dibutyl ether; ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, Aliphatic ethers such as diethylene glycol dibutyl ether; aromatic ethers such as diphenyl ether and anisole. Tertiary amines include triethylamine, tripropylamine, tributylamine, N, N, N ′, N′-tetramethylethylenediamine, N, N-diethylaniline, pyridine, and quinoline. Examples of the phosphine compound include trimethylphosphine, triethylphosphine, and triphenylphosphine. One or more of these are used.

The polymerization temperature in the polymerization step of the above production method is usually 25 to 100 ° C, preferably 35 to 90 ° C. More preferably, it is 50-80 degreeC. The polymerization time is usually 10 minutes to 5 hours.

（式中、ｍ^５は１又は２を表し、ｎ^５は１又は２を表し、ｍ^５＋ｎ^５は２又は３であり、Ｒ^５０１は重合性炭素−炭素二重結合を有するヒドロカルビル基を表し、Ｒ^５０２はヒドロカルビル基を表し、Ｒ^５０２が複数ある場合、複数あるＲ^５０２は同一でも異なっていてもよく、Ｒ^５０３は含酸素置換基を有していてもよいアリール基を表し、Ｒ^５０３が複数ある場合、複数あるＲ^５０３は同一でも異なっていてもよく、Ｒ^５０４はアルキル基、又は置換アミノ基を表す。） The conjugated diene polymer (E) according to the fifth aspect of the present invention has a monomer unit based on a conjugated diene and a monomer unit based on a monomer represented by the following formula (51).

(In the formula, m ⁵ represents 1 or 2, n ⁵ represents 1 or 2, m ⁵ + n ⁵ represents 2 or 3, and R ⁵⁰¹ represents a hydrocarbyl group having a polymerizable carbon-carbon double bond. , ^{R 502} represents a hydrocarbyl ^{group, if R 502} is more, a plurality of ^{R 502} may be the same or ^{different, R 503} represents an aryl group which may have an oxygen-containing ^{substituent, R 503} When there are a plurality of R ^503s , the plurality of R ^503s may be the same or different, and R ⁵⁰⁴ represents an alkyl group or a substituted amino group.)

As used herein, a hydrocarbyl group represents a hydrocarbon residue. The hydrocarbyloxy group represents a group in which a hydrogen atom of a hydroxyl group is substituted with a hydrocarbyl group. The hydrocarbylene group represents a divalent hydrocarbon residue.

Examples of the conjugated diene include 1,3-butadiene, isoprene, 1,3-pentadiene, 2,3-dimethyl-1,3-butadiene, 1,3-hexadiene and the like, and one or more of these are used. . The conjugated diene is preferably 1,3-butadiene or isoprene.

R ⁵⁰¹ is a hydrocarbyl group having a polymerizable carbon-carbon double bond, and R ⁵⁰¹ is preferably a group represented by the following formula (52).

（式中、ｐ^５は０又は１であり、Ｒ^５０５は水素原子又はヒドロカルビル基を表し、Ｔ^５０１はヒドロカルビレン基を表す。）

(In the formula, p ⁵ is 0 or 1, R ⁵⁰⁵ represents a hydrogen atom or a hydrocarbyl group, and T ⁵⁰¹ represents a hydrocarbylene group.)

In the formula (52), p ⁵ represents 0 or 1.

^Examples of the hydrocarbyl group for R ⁵⁰⁵ include an alkyl group and an alkenyl group. Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, and a tert-butyl group, and a methyl group is preferable. Examples of the alkenyl group include a vinyl group, an allyl group, a 1-propenyl group, and a 1-methylethenyl group, and a vinyl group is preferable.

R ⁵⁰⁵ is preferably a hydrogen atom, a methyl group, or a vinyl group, and more preferably a hydrogen atom.

^Examples of the hydrocarbylene group for T ⁵⁰¹ include an alkylene group, an arylene group, and a group in which an arylene group and an alkylene group are bonded.

Examples of the alkylene group include a methylene group, an ethylene group, and a trimethylene group. Preferably, it is a methylene group or an ethylene group. Examples of the arylene group include a phenylene group, a naphthylene group, and a biphenylene group. A phenylene group is preferred.

Examples of the group in which an arylene group and an alkylene group are bonded include a group in which a phenylene group and an alkylene group are bonded, a group in which a naphthylene group and an alkylene group are bonded, and a group in which a biphenylene group and an alkylene group are bonded. . In a group in which a phenylene group and an alkylene group are bonded (phenylene-alkylene group), depending on the position of the carbon atom on the benzene ring from which the hydrogen atom is removed and the position of the carbon atom on the benzene ring to which the alkylene group is bonded, A para-phenylene-alkylene group (for example, a group represented by the following formula (52a)), a meta-phenylene-alkylene group (for example, a group represented by the following formula (52b)), an ortho-phenylene-alkylene group. (For example, a group represented by the following formula (52c)).

Moreover, as the group in which the arylene group and the alkylene group are bonded, it is preferable that the carbon atom of the arylene group of the group is bonded to the carbon atom to which R ⁵⁰⁵ of the formula (52) is bonded.

（式中、ｒ^５、ｓ^５、ｔ^５は、夫々、１〜１０の整数を表す。）

(Wherein, r ⁵ , s ⁵ and t ⁵ each represents an integer of 1 to 10)

The group in which an arylene group and an alkylene group are bonded (phenylene-alkylene group) is preferably a group in which a phenylene group and an alkylene group are bonded, more preferably a group represented by the above formula (52a), A group represented by the above formula (52b), more preferably a para-phenylene-methylene group (a group represented by the formula (52a) where r ⁵ = 1), a meta-phenylene-methylene group (s ⁵ = 1 group represented by formula (52b)), para-phenylene-ethylene group (group represented by formula (52a) where r ⁵ = 2), meta-phenylene-ethylene group (s ⁵ = 2). A group represented by the formula (52b).

When R ⁵⁰⁵ is a methyl group, p ⁵ is preferably 1, and T ⁵⁰¹ is preferably a group in which an arylene group and an alkylene group are bonded or an arylene group, more preferably a phenylene group and an alkylene group. And a phenylene group, more preferably a phenylene group, para-phenylene-methylene group, meta-phenylene-methylene group, para-phenylene-ethylene group, meta-phenylene-ethylene. It is a group.

When R ⁵⁰⁵ is a vinyl group and p ⁵ is 1, T ⁵⁰¹ is preferably an alkylene group, more preferably a methylene group or an ethylene group.

The group represented by the formula (52) is preferably a group in which R ⁵⁰⁵ is a hydrogen atom, such as vinyl group, vinylmethyl group, vinylethyl group, 4-vinylphenyl group, 3-vinylphenyl group, (4- Vinylphenyl) methyl group, 2- (4-vinylphenyl) ethyl group, (3-vinylphenyl) methyl group, 2- (3-vinylphenyl) ethyl group, and R ⁵⁰⁵ is a methyl group, 4-isopropenylphenyl group, 3-isopropenylphenyl group, (4-isopropenylphenyl) methyl group, 2- (4-isopropenylphenyl) ethyl group, (3-isopropenylphenyl) methyl group, 2- (3 - isopropenyl phenyl) ethyl group and the ^like, as a base ^{R 505} is a vinyl group, 1-methylene-2-propenyl group, 2-methylene-3 Butenyl group and the like.

R ⁵⁰¹ is preferably a vinyl group, a 4-vinylphenyl group, or a 3-vinylphenyl group, and more preferably a vinyl group.

^Examples of the hydrocarbyl group of R ⁵⁰² include an alkyl group and an aryl group.

^Examples of the alkyl group for R ⁵⁰² include a methyl group; a primary alkyl group such as an ethyl group, an n-propyl group, and an n-pentyl group (an alkyl group in which a carbon atom from which a hydrogen atom has been removed is a primary carbon atom); Secondary alkyl groups such as isopropyl group, sec-butyl group and 2-ethylhexyl group (alkyl groups in which a carbon atom from which a hydrogen atom has been removed is a secondary carbon atom); tert-butyl group, tert-pentyl group and the like A tertiary alkyl group (an alkyl group in which a carbon atom from which a hydrogen atom has been removed is a tertiary carbon atom) can be mentioned.

^Examples of the aryl group of R ⁵⁰² include a phenyl group, a tolyl group, and a xylyl group.

The number of carbon atoms of the hydrocarbyl group of R ⁵⁰² is preferably 3 to 10, more preferably 4 to 8.

The hydrocarbyl group for R ⁵⁰² is preferably a secondary alkyl group or a tertiary alkyl group, more preferably a tertiary alkyl group, and still more preferably a tert-butyl group.

R ⁵⁰³ is an aryl group which may have an oxygen-containing substituent. Here, the aryl group having an oxygen-containing substituent represents a group in which a hydrogen atom of the aryl group is substituted with an oxygen-containing substituent.

The aryl group of R ⁵⁰³ includes a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a phenyl group substituted with an alkyl group, a 1-naphthyl group substituted with an alkyl group, and a 2-naphthyl substituted with an alkyl group. You can raise a group.

Examples of the alkyl group include: methyl group; primary alkyl group such as ethyl group, n-propyl group and n-butyl group; secondary alkyl group such as isopropyl group, sec-butyl group and 2-ethylhexyl group; And tertiary alkyl groups such as a tert-pentyl group.

Examples of the phenyl group substituted with an alkyl group include methylphenyl group, ethylphenyl group, n-propylphenyl group, isopropylphenyl group, n-butylphenyl group, sec-butylphenyl group, tert-butylphenyl group, and tert-pentyl. A phenyl group, a (2-ethylhexyl) phenyl group, etc. can be mentioned.

Examples of 1-naphthyl group substituted with an alkyl group include methyl-1-naphthyl group, ethyl-1-naphthyl group, n-propyl-1-naphthyl group, isopropyl-1-naphthyl group, and n-butyl-1-naphthyl group. Group, sec-butyl-1-naphthyl group, tert-butyl-1-naphthyl group, tert-pentyl-1-naphthyl group, (2-ethylhexyl) -1-naphthyl group, and the like.

Examples of the 2-naphthyl group substituted with an alkyl group include methyl-2-naphthyl group, ethyl-2-naphthyl group, n-propyl-2-naphthyl group, isopropyl-2-naphthyl group, and n-butyl-2-naphthyl group. Group, sec-butyl-2-naphthyl group, tert-butyl-2-naphthyl group, tert-pentyl-2-naphthyl group, (2-ethylhexyl) -2-naphthyl group and the like.

The aryl group having an oxygen-containing substituent is an alkoxy group such as a methoxy group, an ethoxy group, an isopropoxy group or a tert-butoxy group; an alkoxyalkyl group such as a methoxymethyl group, an ethoxymethyl group, a methoxyethyl group or an ethoxyethyl group An aryl group having an alkoxyalkoxy group such as a methoxymethoxy group, an ethoxymethoxy group, a methoxyethoxy group, or an ethoxyethoxy group.

Examples of the phenyl group having an alkoxy group include a methoxyphenyl group, an ethoxyphenyl group, an isopropoxyphenyl group, and a tert-butoxyphenyl group. Examples of the phenyl group having an alkoxyalkyl group include (methoxymethyl) phenyl group, (ethoxymethyl) phenyl group, (methoxyethyl) phenyl group, and (ethoxyethyl) phenyl group. Examples of the phenyl group having an alkoxyalkoxy group include (methoxymethoxy) phenyl group, (ethoxymethoxy) phenyl group, (methoxyethoxy) phenyl group, and (ethoxyethoxy) phenyl group.

Examples of the 1-naphthyl group having an alkoxy group include a methoxy-1-naphthyl group, an ethoxy-1-naphthyl group, an isopropoxy-1-naphthyl group, and a tert-butoxy-1-naphthyl group. Examples of the 1-naphthyl group having an alkoxyalkyl group include (methoxymethyl) -1-naphthyl group, (ethoxymethyl) -1-naphthyl group, (methoxyethyl) -1-naphthyl group, and (ethoxyethyl) -1-naphthyl. You can raise a group. Examples of the 1-naphthyl group having an alkoxyalkoxy group include (methoxymethoxy) -1-naphthyl group, (ethoxymethoxy) -1-naphthyl group, (methoxyethoxy) -1-naphthyl group, and (ethoxyethoxy) -1-naphthyl. You can raise a group.

Examples of the 2-naphthyl group having an alkoxy group include a methoxy-2-naphthyl group, an ethoxy-2-naphthyl group, an isopropoxy-2-naphthyl group, and a tert-butoxy-2-naphthyl group. Examples of the 2-naphthyl group having an alkoxyalkyl group include (methoxymethyl) -2-naphthyl group, (ethoxymethyl) -2-naphthyl group, (methoxyethyl) -2-naphthyl group, and (ethoxyethyl) -2-naphthyl. You can raise a group. Examples of the 2-naphthyl group having an alkoxyalkoxy group include (methoxymethoxy) -2-naphthyl group, (ethoxymethoxy) -2-naphthyl group, (methoxyethoxy) -2-naphthyl group, and (ethoxyethoxy) -2-naphthyl. You can raise a group.

Examples of the mono-substituted phenyl group include a 2-substituted phenyl group, a 3-substituted phenyl group, and a 4-substituted phenyl group depending on the substitution position. The phenyl group substituted with the above alkyl group or oxygen-containing substituent may be a disubstituted or trisubstituted product, and depending on the substitution position and the number of substitutions, a 2,3-disubstituted phenyl group, 2, 4-disubstituted phenyl group, 2,5-disubstituted phenyl group, 2,6-disubstituted phenyl group, 3,4-disubstituted phenyl group, 3,5-disubstituted phenyl group, 2,3,4-tri Substituted phenyl group, 2,3,5-trisubstituted phenyl group, 2,4,5-trisubstituted phenyl group, 2,4,6-trisubstituted phenyl group, 3,4,5-trisubstituted phenyl group, etc. It is done.

The mono-substituted 1-naphthyl group may be a 2-substituted 1-naphthyl group, a 3-substituted 1-naphthyl group, a 4-substituted 1-naphthyl group, a 5-substituted 1-naphthyl group, or a 6-substituted, depending on the substitution position. A 1-naphthyl group can be mentioned. Further, the 1-naphthyl group substituted with the above alkyl group or oxygen-containing substituent may be a di- or 3-substituent, and may be a 4,5-disubstituted 1-naphthyl group, 4,8-di- Substituted 1-naphthyl group, 5,8-disubstituted 1-naphthyl group, 6,7-disubstituted 1-naphthyl group, 3,8-disubstituted 1-naphthyl group, 6,8-disubstituted 1-naphthyl group, 4,5,8-trisubstituted 1-naphthyl group and the like.

The mono-substituted 2-naphthyl group may be a 1-substituted 2-naphthyl group, a 3-substituted 2-naphthyl group, a 4-substituted 2-naphthyl group, a 5-substituted 2-naphthyl group, or a 6-substituted, depending on the substitution position. A 2-naphthyl group can be mentioned. Further, the 1-naphthyl group substituted with the above alkyl group or oxygen-containing substituent may be a di- or 3-substituent, such as a 3,5-disubstituted 2-naphthyl group, 3,8-di- Examples thereof include a substituted 2-naphthyl group, a 4,5-disubstituted 2-naphthyl group, and a 1,4,5-trisubstituted 2-naphthyl group.

R ⁵⁰³ preferably has 6 to 10 carbon atoms, more preferably 6 to 8 carbon atoms.

R ⁵⁰³ is preferably a phenyl group or a phenyl group substituted with an alkyl group. The phenyl group substituted with an alkyl group is preferably a 4-alkylphenyl group, more preferably a 4-methylphenyl group, a 4-ethylphenyl group, a 4-n-propylphenyl group, a 4-n- It is a butylphenyl group.

R ⁵⁰³ is more preferably a phenyl group, a 4-methylphenyl group, or a 4-ethylphenyl group, and even more preferably a phenyl group.

^Examples of the alkyl group for R ⁵⁰⁴ include a methyl group and an ethyl group.

（式中、Ｒ^５０６及びＲ^５０７は、それぞれ、ヒドロカルビル基、又は、トリヒドロカルビルシリル基を表し、あるいは、Ｒ^５０６とＲ^５０７は結合して、窒素原子及び／又は酸素原子をヘテロ原子として有していてもよいヒドロカルビレン基、又は、Ｒ^５０６とＲ^５０７は１つの基であって、窒素原子に二重結合で結合する基を表す。） ^Examples of the substituted amino group for R ⁵⁰⁴ include a group represented by the following formula (53).

(Wherein R ⁵⁰⁶ and R ⁵⁰⁷ each represent a hydrocarbyl group or a trihydrocarbyl silyl group, or R ⁵⁰⁶ and R ⁵⁰⁷ are bonded to each other and have a nitrogen atom and / or an oxygen atom as a hetero atom. And an optional hydrocarbylene group, or R ⁵⁰⁶ and R ⁵⁰⁷ are one group and represent a group bonded to a nitrogen atom by a double bond.)

^Examples of the hydrocarbyl group of R ⁵⁰⁶ and R ⁵⁰⁷ include an alkyl group and an aryl group. Examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, and tert-butyl group. A phenyl group etc. can be mention | raise | lifted as an aryl group. Preferably it is an alkyl group, More preferably, it is a C1-C4 alkyl group.

The trihydrocarbyl silyl group R ⁵⁰⁶ and R ^507, may be mentioned trimethylsilyl group, triethylsilyl group, triisopropylsilyl group, a trialkylsilyl group such as tert- butyldimethylsilyl group. A trialkylsilyl group having 3 to 9 carbon atoms is preferable, and a trialkylsilyl group in which an alkyl group bonded to a silicon atom is an alkyl group having 1 to 3 carbon atoms is more preferable.

^{Examples of the} hydrocarbylene group optionally having a nitrogen atom and / or oxygen atom bonded to R ⁵⁰⁶ and R ⁵⁰⁷ as a hetero atom include an ethylene group, a trimethylene group, a tetramethylene group, a pentamethylene group, a hexamethylene group, and the like. An alkylene group; a group represented by —CH ₂ CH ₂ —NH—CH ₂ —, a group represented by —CH ₂ CH ₂ —N═CH—, and a group represented by —CH═CH—N═CH—. Group, a hydrocarbylene group having a nitrogen atom such as a group represented by —CH ₂ CH ₂ —NH—CH ₂ CH ₂ —; a group represented by —CH ₂ CH ₂ —O—CH ₂ CH ₂ —, etc. And a hydrocarbylene group having an oxygen atom.

In the present specification, the hydrocarbylene group having an X atom as a hetero atom represents a group having a structure in which a hydrogen atom and / or a carbon atom of the hydrocarbylene group is replaced with an X atom. For example, examples of the hydrocarbylene group having a nitrogen atom as a hetero atom include a group having a structure in which CH in the hydrocarbylene group is replaced with N. Examples of the hydrocarbylene group having an oxygen atom as a hetero atom include a group having a structure in which CH ₂ is replaced with O and a group having a structure in which two hydrogen atoms are replaced with O.

Examples of one group in which R ⁵⁰⁶ and R ⁵⁰⁷ are bonded to the nitrogen atom with a double bond include ethylidene group, propylidene group, butylidene group, 1-methylethylidene group, 1-methylpropylidene group, 1,3-dimethylbutylidene Group.

R ⁵⁰⁴ is preferably an alkyl group such as a methyl group or an ethyl group, or a dialkylamino group such as a dimethylamino group, a diethylamino group, a di (n-propyl) amino group, or a di (n-butyl) amino group.

In Formula (51), n ⁵ represents 1 or 2, and m ⁵ + n ⁵ is 2 or 3. Preferably, m ⁵ + n ⁵ is 3. More preferably, m ⁵ is 1 and n ⁵ is 2.

As the compound represented by the formula (51), as a compound in which R ⁵⁰⁵ is a hydrogen atom and p ⁵ = 0,
tert-butoxydiphenylvinylsilane,
tert-pentoxydiphenylvinylsilane,
Di (tert-butoxy) phenylvinylsilane,
Di (tert-pentoxy) phenylvinylsilane,
tert-butoxymethylphenylvinylsilane,
tert-butoxyethylphenylvinylsilane,
Dimethylamino tert-butoxyphenylvinylsilane,
Examples thereof include diethylamino tert-butoxyphenylvinylsilane.

In addition, as a compound represented by the formula (51), as a compound in which R ⁵⁰⁵ is a hydrogen atom and p ⁵ = 1,
tert-butoxydiphenyl-4-vinylphenylsilane,
tert-butoxydiphenyl-3-vinylphenylsilane,
Di (tert-butoxy) phenyl-4-vinylphenylsilane,
Di (tert-butoxy) phenyl-3-vinylphenylsilane,
tert-butoxymethylphenyl-4-vinylphenylsilane,
tert-butoxymethylphenyl-3-vinylphenylsilane,
tert-butoxyethylphenyl-4-vinylphenylsilane,
tert-butoxyethylphenyl-3-vinylphenylsilane,
Dimethylamino tert-butoxyphenyl-4-vinylphenylsilane,
Dimethylamino tert-butoxyphenyl-3-vinylphenylsilane,
Diethylamino tert-butoxyphenyl-4-vinylphenylsilane,
Diethylamino tert-butoxyphenyl-3-vinylphenylsilane,
Etc.

As the compound represented by the formula (51), as a compound in which R ⁵⁰⁵ is a methyl group and p ⁵ = 1,
tert-butoxydiphenyl-4-isopropenylphenylsilane,
tert-butoxydiphenyl-3-isopropenylphenylsilane,
Di (tert-butoxy) phenyl-4-isopropenylphenylsilane,
Di (tert-butoxy) phenyl-3-isopropenylphenylsilane,
tert-butoxymethylphenyl-4-isopropenylphenylsilane,
tert-butoxymethylphenyl-3-isopropenylphenylsilane,
tert-butoxyethylphenyl-4-isopropenylphenylsilane,
tert-butoxyethylphenyl-3-isopropenylphenylsilane,
Dimethylamino tert-butoxyphenyl-4-isopropenylphenylsilane,
Dimethylamino tert-butoxyphenyl-3-isopropenylphenylsilane,
Diethylamino tert-butoxyphenyl-4-isopropenylphenylsilane,
Diethylamino tert-butoxyphenyl-3-isopropenylphenylsilane,
Etc.

The compound represented by the formula (51) is preferably a compound in which R ⁵⁰⁵ is a hydrogen atom and p ⁵ = 0.
More preferably,
tert-butoxydiphenylvinylsilane,
Di (tert-butoxy) phenylvinylsilane,
tert-butoxymethylphenylvinylsilane,
Dimethylamino-tert-butoxyphenylvinylsilane,
Diethylamino-tert-butoxyphenylvinylsilane;
More preferably, tert-butoxydiphenylvinylsilane,
Di (tert-butoxy) phenylvinylsilane,
Particularly preferred is tert-butoxydiphenylvinylsilane.

The content of the monomer unit based on the compound represented by the formula (51) is preferably 0.01% by mass or more, more preferably, per 100% by mass of the conjugated diene polymer in order to increase the strength. It is 0.02 mass% or more. Moreover, in order to improve economical efficiency, Preferably it is 2 mass% or less, More preferably, it is 1 mass% or less.

In the conjugated diene polymer (E), a monomer unit based on the monomer represented by the formula (51) is present in the chain, that is, a partial chain having a monomer unit based on the conjugated diene ( The partial chain does not have a monomer unit based on the monomer represented by the formula (51).) And a partial chain having a monomer unit based on a conjugated diene (the partial chain includes The monomer unit based on the monomer represented by the formula (51) or the formula (51). It is preferable to have a partial chain consisting of monomer units based on the monomer represented by 51).

The conjugated diene polymer (E) preferably has monomer units (vinyl aromatic hydrocarbon units) based on vinyl aromatic hydrocarbons in order to increase strength. Examples of the vinyl aromatic hydrocarbon include styrene, α-methylstyrene, vinyl toluene, vinyl naphthalene, divinyl benzene, trivinyl benzene, and divinyl naphthalene. Styrene is preferable.

As the content of the vinyl aromatic hydrocarbon unit, the total amount of the conjugated diene unit and the vinyl aromatic hydrocarbon unit is 100% by mass, preferably 10% by mass or more (the content of the conjugated diene unit is 90% by mass or less). More preferably, it is 15% by mass or more (the content of the conjugated diene unit is 85% by mass or less). In order to improve fuel economy, the content of vinyl aromatic hydrocarbon units is preferably 50% by mass or less (the content of conjugated diene units is 50% by mass or more), more preferably 45% by mass or less. (The content of the conjugated diene unit is 55% by mass or more).

The Mooney viscosity (ML _{1 + 4} ) of the conjugated diene polymer (E) is preferably 10 or more, more preferably 20 or more, in order to increase the strength. Moreover, in order to improve workability, Preferably it is 200 or less, More preferably, it is 150 or less. The Mooney viscosity (ML _{1 + 4} ) is measured at 100 ° C. according to JIS K6300 (1994).

The vinyl bond amount of the conjugated diene polymer (E) is preferably 80 mol% or less, more preferably 70 mol% or less, in order to improve fuel efficiency, with the content of the conjugated diene unit being 100 mol%. It is. Moreover, in order to improve grip property, Preferably it is 10 mol% or more, More preferably, it is 15 mol% or more, More preferably, it is 20 mol% or more, Most preferably, it is 40 mol% or more. The vinyl bond amount is determined from the absorption intensity in the vicinity of 910 cm ^−1, which is the absorption peak of the vinyl group, by infrared spectroscopy.

The molecular weight distribution of the conjugated diene polymer (E) is preferably 1.0 to 5.0, more preferably 1.0 to 1.5, in order to improve fuel efficiency. The molecular weight distribution is determined by measuring the number average molecular weight (Mn) and the weight average molecular weight (Mw) by gel permeation chromatography (GPC) method and dividing Mw by Mn.

As a preferred method for producing the conjugated diene polymer (E), a monomer component containing the conjugated diene and the compound represented by the above formula (51) is polymerized with an alkali metal catalyst in a hydrocarbon solvent. I can give you a way.

Examples of the alkali metal catalyst include alkali metals, organic alkali metal compounds, complexes of alkali metals and polar compounds, oligomers having alkali metals, and the like. Examples of the alkali metal include lithium, sodium, potassium, rubidium, cesium and the like. Examples of the organic alkali metal compound include ethyl lithium, n-propyl lithium, iso-propyl lithium, n-butyl lithium, sec-butyl lithium, t-octyl lithium, n-decyl lithium, phenyl lithium, 2-naphthyl lithium, 2 -Butylphenyllithium, 4-phenylbutyllithium, cyclohexyllithium, 4-cyclopentyllithium, dimethylaminopropyllithium, diethylaminopropyllithium, t-butyldimethylsiloxypropyllithium, N-morpholinopropyllithium, lithium hexamethyleneimide, lithium pyrrole Zido, lithium piperidide, lithium heptamethylene imide, lithium dodecamethylene imide, 1,4-dilithio-2-butene, sodium naphthalenide, sodium Bifenirido, such as potassium napthalenide can be mentioned. Examples of the complex of the alkali metal and the polar compound include potassium-tetrahydrofuran complex and potassium-diethoxyethane complex, and the oligomer having the alkali metal includes sodium salt of α-methylstyrene tetramer. I can give you. An organic lithium compound or an organic sodium compound is preferable, and an organic lithium compound having 2 to 20 carbon atoms or an organic sodium compound having 2 to 20 carbon atoms is more preferable.

The hydrocarbon solvent is a solvent that does not deactivate the organic alkali metal compound catalyst, and examples thereof include aliphatic hydrocarbons, aromatic hydrocarbons, and alicyclic hydrocarbons. Examples of the aliphatic hydrocarbon include propane, n-butane, iso-butane, n-pentane, iso-pentane, n-hexane, propene, 1-butene, iso-butene, trans-2-butene, cis-2- Examples include butene, 1-pentene, 2-pentene, 1-hexene, 2-hexene and the like. Examples of the aromatic hydrocarbon include benzene, toluene, xylene, and ethylbenzene. Examples of the alicyclic hydrocarbon include cyclopentane and cyclohexane. One or more of these may be used, and the hydrocarbon solvent may be a mixture of various components such as industrial hexane. Preferably, it is a hydrocarbon having 2 to 12 carbon atoms.

In a hydrocarbon solvent, a monomer component containing a conjugated diene and a compound represented by the above formula (51) is polymerized with an alkali metal catalyst, and the monomer unit based on the conjugated diene and the above formula (51) A polymer having a monomer unit based on the represented compound is produced. Examples of the conjugated diene include 1,3-butadiene, isoprene, 1,3-pentadiene, 2,3-dimethyl-1,3-butadiene, and 1,3-hexadiene. One or more of these are used. 1,3-butadiene and isoprene are preferred.

The amount of the compound represented by the formula (51) is preferably 0.01% by mass or more in order to increase the strength, with the total amount of monomer components used in the polymerization being 100% by mass. Preferably it is 0.02 mass% or more. Moreover, in order to improve economical efficiency, Preferably it is 2 mass% or less, More preferably, it is 1 mass% or less.

As a monomer, a conjugated diene and a compound represented by the formula (51) may be combined with a vinyl aromatic hydrocarbon to perform polymerization. Examples of the vinyl aromatic hydrocarbon include styrene, α-methylstyrene, Examples thereof include vinyl toluene, vinyl naphthalene, divinyl benzene, trivinyl benzene, divinyl naphthalene and the like. Styrene is preferable.

The amount of vinyl aromatic hydrocarbon used is 0% by mass or more (the amount of conjugated diene used is 100% by mass or less), where the total amount of conjugated diene and vinyl aromatic hydrocarbon is 100% by mass. In order to increase it, it is preferably 10% by mass or more (the amount of conjugated diene used is 90% by mass or less), more preferably 15% by mass or more (the amount of conjugated diene used is 85% by mass or less). In order to improve fuel efficiency, the amount of vinyl aromatic hydrocarbon used is preferably 50% by mass or less (the amount of conjugated diene used is 50% by mass or more), more preferably 45% by mass or less (conjugated). The amount of diene used is 55% by mass or more).

Polymerization reaction is an agent that adjusts the amount of vinyl bonds of conjugated diene units, an agent that adjusts the distribution of monomer units based on monomers other than conjugated diene units and conjugated dienes in the conjugated diene polymer chain , Generally referred to as “regulators”). Examples of such agents include ether compounds, tertiary amines, and phosphine compounds. Examples of the ether compound include cyclic ethers such as tetrahydrofuran, tetrahydropyran, and 1,4-dioxane; aliphatic monoethers such as diethyl ether and dibutyl ether; ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, and diethylene glycol diethyl ether. And aliphatic ethers such as diethylene glycol dibutyl ether; aromatic ethers such as diphenyl ether and anisole. Examples of the tertiary amine include triethylamine, tripropylamine, tributylamine, N, N, N ′, N′-tetramethylethylenediamine, N, N-diethylaniline, pyridine, quinoline and the like. Examples of the phosphine compound include trimethylphosphine, triethylphosphine, triphenylphosphine, and the like. One or more of these are used.

The polymerization temperature is usually 25 to 100 ° C, preferably 35 to 90 ° C, more preferably 50 to 80 ° C. The polymerization time is usually 10 minutes to 5 hours.

（式中、ｌ^６〜ｎ^６は、独立に、１〜８の整数を表す。） The conjugated diene polymer (F) according to the sixth aspect of the present invention is an alkali metal catalyst comprising a conjugated diene monomer or a conjugated diene monomer and an aromatic vinyl monomer in a hydrocarbon solvent in the presence of a Lewis basic compound. It can be obtained by reacting a compound represented by the following formula (61) with an active conjugated diene polymer having an alkali metal terminal obtained by polymerization.

(Wherein l ^{6 to} n ⁶ independently represent an integer of 1 to 8)

Examples of the conjugated diene monomer include 1,3-butadiene, isoprene, 1,3-pentadiene (piperine), 2,3-dimethyl-1,3-butadiene, 1,3-hexadiene, and the like. Then, 1,3-butadiene and isoprene are preferred from the viewpoint of the physical properties of the resulting polymer and the availability for industrial implementation.

Examples of the aromatic vinyl monomer include styrene, α-methylstyrene, vinyl toluene, vinyl naphthalene, divinyl benzene, trivinyl benzene, divinyl naphthalene and the like. Among these, the physical properties of the resulting polymer, industrial Styrene is preferable from the viewpoint of availability in carrying out.

The hydrocarbon solvent is one that does not deactivate the alkali metal catalyst, and the suitable hydrocarbon solvent is selected from aliphatic hydrocarbons, aromatic hydrocarbons, and alicyclic hydrocarbons, particularly having 3 to 12 carbon atoms. Propane, n-butane, iso-butane, n-pentane, iso-pentane, n-hexane, cyclohexane, propene, 1-butene, iso-butene, trans-2-butene, cis-2-butene, 1 -Pentene, 2-pentene, 1-hexene, 2-hexene, benzene, toluene, xylene, ethylbenzene and the like. Moreover, these hydrocarbon solvents can be used in mixture of 2 or more types.

Examples of the alkali metal catalyst include metals such as lithium, sodium, potassium, rubidium, and cesium, hydrocarbon compounds containing these metals, and complexes of the metals with polar compounds. Preferred examples of the alkali metal catalyst include lithium or sodium compounds having 2 to 20 carbon atoms. Specific examples thereof include ethyl lithium, n-propyl lithium, and iso-propyl lithium. N-butyl lithium, sec-butyl lithium, t-octyl lithium, n-decyl lithium, phenyl lithium, 2-naphthyl lithium, 2-butyl-phenyl lithium, 4-phenyl-butyl lithium, cyclohexyl lithium 4-cyclopentyl lithium, Examples include 1,4-dilithio-butene-2, sodium naphthalene, sodium biphenyl, potassium-tetrahydrofuran complex, potassium diethoxyethane complex, and sodium salt of α-methylstyrene tetramer.

As the modified compound to be reacted with the active diene polymer rubber used in the present invention, a compound represented by the above formula (61) is used, and l ^{6 to} n ⁶ are independently preferably integers of 1 to 8, In order to improve fuel efficiency, triglycidyl isocyanurate, in which l ^{6 to} n ⁶ are all 1, is most preferable.

As the polymerization monomer, only a conjugated diene monomer may be used, or a conjugated diene monomer and an aromatic vinyl monomer may be used in combination. When the conjugated diene monomer and the aromatic vinyl monomer are used in combination, the weight ratio of conjugated diene monomer / aromatic vinyl monomer is preferably 50/50 to 90/10, more preferably 55/45 to 85/15. It is. If the ratio is too small, the polymer rubber becomes insoluble in the hydrocarbon solvent, and uniform polymerization may not be possible. On the other hand, if the ratio is too large, the strength of the polymer rubber may decrease.

In the polymerization, it is possible to use commonly used materials such as an alkali metal catalyst, a hydrocarbon solvent, a reagent for improving random polymerizability, and a vinyl bond content regulator for conjugated diene units. The polymerization temperature in the production of the copolymer is not particularly limited, but is usually −80 ° C. to 150 ° C., and preferably 20 to 110 ° C. from the viewpoint of the reaction rate and the stability of the alkali metal catalyst. The polymerization time is not particularly limited, but the alkali metal catalyst is completed within at least 24 hours.

In order to adjust the vinyl bond content of the conjugated diene part, various compounds can be used as the Lewis basic compound. However, ether compounds or tertiary amines are easily available in industrial implementation. preferable. Examples of ether compounds include cyclic ethers such as tetrahydrofuran, tetrahydropyran, and 1,4-dioxane; aliphatic monoethers such as diethyl ether and dibutyl ether; ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, Examples thereof include aliphatic ethers such as diethylene glycol dibutyl ether; aromatic ethers such as diphenyl ether and anisole. Examples of tertiary amines include triethylamine, tripropylamine, tributylamine, N, N, N ′, N′-tetramethylethylenediamine, N-diethylaniline, pyridine, quinoline, and the like. Can do.

The amount used when the modified compound represented by the formula (61) is added to the active conjugated diene polymer having an alkali metal terminal to produce is per mol of the alkali metal catalyst used when adding the alkali metal. Usually, it is 0.06-10 mol, Preferably it is 0.1-5 mol, More preferably, it is 0.2-2 mol. If the amount used is too small, the effect of improving fuel economy is small, and if it is too large, it remains in the polymerization solvent. Therefore, when the solvent is recycled, a separation step from the solvent is required. Etc., not economically desirable.

Since the reaction between the modifying compound and the active conjugated diene polymer having an alkali metal terminal occurs rapidly, the reaction temperature and reaction time can be selected in a wide range, but generally room temperature to 100 ° C., several seconds to A few hours. The reaction may be performed by bringing the alkali metal-containing diene polymer and the modified compound into contact with each other. For example, an alkali metal catalyst is used to polymerize the diene polymer, and the modified compound is placed in the polymer solution. Although the method of adding quantitatively can be illustrated as a preferred embodiment, it is not limited to this method.

The conjugated diene polymer (F) obtained by reacting the modified compound represented by the formula (61) with an active conjugated diene polymer having an alkali metal terminal is prepared by adding a coagulant or steam from the reaction solvent. The coagulation method used in the production of rubber by ordinary solution polymerization such as coagulation is used as it is, and the coagulation temperature is not limited at all.

For drying the crumb separated from the reaction system, a band drier, an extrusion drier or the like used in the production of ordinary synthetic rubber can be used, and the drying temperature is not limited at all.

The Mooney viscosity (ML _{1 + 4} ) of the conjugated diene polymer (F) is preferably 10 to 200, more preferably 20 to 150. If the Mooney viscosity is too low, mechanical properties such as the tensile strength of the vulcanizate may be reduced. On the other hand, if the viscosity is too high, the miscibility is poor when used in combination with other rubbers, and the processing operability is difficult. Thus, the mechanical properties of the vulcanizate of the obtained rubber composition may be deteriorated.

The vinyl bond content of the conjugated diene part of the conjugated diene polymer (F) is preferably 20 to 70 mol%, more preferably 25 to 65 mol%, with the content of the conjugated diene unit being 100 mol%. is there. If it is less than 20 mol%, the grip performance may be inferior, and if it exceeds 70 mol%, the fuel efficiency may be inferior.

The molecular weight distribution of the conjugated diene polymer (F) is preferably 1.0 to 5.0, more preferably 1.0 to 1.5, in order to improve fuel efficiency. The molecular weight distribution is determined by measuring the number average molecular weight (Mn) and the weight average molecular weight (Mw) by gel permeation chromatography (GPC) method and dividing Mw by Mn.

（式中、Ｒ^７１１は水素原子又は炭素原子数１〜５のヒドロカルビル基を表し、ｍ^７は０又は１であり、Ｒ^７１２はヒドロカルビレン基を表し、Ｒ^７１３及びＲ^７１４は、それぞれ、ヒドロカルビル基、又は、トリヒドロカルビルシリル基、あるいは、Ｒ^７１３とＲ^７１４とが結合して、窒素原子及び／又は酸素原子を有していてもよいヒドロカルビレン基、又は、Ｒ^７１３とＲ^７１４は１つの基であって、窒素原子に二重結合で結合する基を表す。）

（式中、ｎ^７は１〜１０の整数を表し、Ｒ^７２１、Ｒ^７２２及びＲ^７２３は、それぞれ、ヒドロカルビル基又はヒドロカルビルオキシ基を表し、Ｒ^７２１、Ｒ^７２２及びＲ^７２３の少なくとも１つがヒドロカルビルオキシ基であり、Ｒ^７２４及びＲ^７２５は、それぞれ、水素原子、窒素原子及び／又は酸素原子を有していてもよいヒドロカルビル基、あるいは、Ｒ^７２４とＲ^７２５とが結合して、窒素原子及び／又は酸素原子を有していてもよいヒドロカルビレン基、又は、Ｒ^７２４とＲ^７２５は１つの基であって、窒素原子に二重結合で結合する基を表す。） The conjugated diene polymer (G) according to the seventh aspect of the present invention is a conjugated diene system having a monomer unit based on a conjugated diene and a monomer unit based on a monomer represented by the following formula (71) It is obtained by reacting one end of the polymer with a compound represented by the following formula (72).

Wherein R ⁷¹¹ represents a hydrogen atom or a hydrocarbyl group having 1 to 5 carbon atoms, m ⁷ is 0 or 1, R ⁷¹² represents a hydrocarbylene group, and R ⁷¹³ and R ⁷¹⁴ are respectively Hydrocarbyl group, trihydrocarbyl silyl group, R ⁷¹³ and R ⁷¹⁴ are bonded to each other, and hydrocarbylene group optionally having nitrogen and / or oxygen atoms, or R ⁷¹³ and R ⁷¹⁴ are 1 group representing a group bonded to a nitrogen atom with a double bond.)

(In the formula, n ⁷ represents an integer of 1 to 10, R ⁷²¹ , R ⁷²² and R ⁷²³ each represents a hydrocarbyl group or a hydrocarbyloxy group, and at least one of R ⁷²¹ , R ⁷²² and R ⁷²³ is hydrocarbyloxy. Each of R ⁷²⁴ and R ⁷²⁵ is a hydrogen carbyl group which may have a hydrogen atom, a nitrogen atom and / or an oxygen atom, or R ⁷²⁴ and R ⁷²⁵ are bonded to each other to form a nitrogen atom and / Or a hydrocarbylene group which may have an oxygen atom, or R ⁷²⁴ and R ⁷²⁵ represent one group which represents a group bonded to a nitrogen atom with a double bond.

As used herein, a hydrocarbyl group represents a hydrocarbon residue. The hydrocarbyloxy group represents a group in which a hydrogen atom of a hydroxyl group is substituted with a hydrocarbyl group. The hydrocarbylene group represents a divalent hydrocarbon residue. Moreover, the hydrocarbyl group having an X atom represents a group having a structure in which a hydrogen atom and / or a carbon atom of the hydrocarbyl group is replaced with an X atom, and the hydrocarbylene group having an X atom is a hydrocarbylene group This represents a group having a structure in which a hydrogen atom and / or a carbon atom is replaced with an X atom. For example, examples of the group having a nitrogen atom include a group having a structure in which CH is replaced by N. Examples of the group having an oxygen atom include a group having a structure in which CH ₂ is replaced with O, and a group having a structure in which two hydrogen atoms are replaced with O.

Examples of the conjugated diene include 1,3-butadiene, isoprene, 1,3-pentadiene, 2,3-dimethyl-1,3-butadiene, 1,3-hexadiene and the like, and one or more of these are used. . The conjugated diene is preferably 1,3-butadiene or isoprene.

R ⁷¹¹ represents a hydrogen atom or a hydrocarbyl group having 1 to 5 carbon atoms.

^Examples of the hydrocarbyl group for R ⁷¹¹ include an alkyl group and an alkenyl group. Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, and a tert-butyl group, and a methyl group is preferable. Examples of the alkenyl group include a vinyl group, an allyl group, a 1-propenyl group, and a 1-methylethenyl group, and a vinyl group is preferable.

R ⁷¹¹ is preferably a hydrogen atom, a methyl group, or a vinyl group.

^Examples of the hydrocarbylene group for R ⁷¹² include an alkylene group, an arylene group, and a group in which an arylene group and an alkylene group are bonded.

Examples of the alkylene group include a methylene group, an ethylene group, and a trimethylene group. Preferably, it is a methylene group or an ethylene group.

Examples of the arylene group include a phenylene group, a naphthylene group, and a biphenylene group. A phenylene group is preferred.

Examples of the group in which an arylene group and an alkylene group are bonded include a group in which a phenylene group and an alkylene group are bonded, a group in which a naphthylene group and an alkylene group are bonded, and a group in which a biphenylene group and an alkylene group are bonded. . A group in which a phenylene group and an alkylene group are bonded is preferable.

Further, as the group in which the arylene group and the alkylene group are bonded, it is preferable that the carbon atom of the arylene group of the group is bonded to the carbon atom to which R ⁷¹¹ of the formula (71) is bonded.

In a group in which a phenylene group and an alkylene group are bonded (phenylene-alkylene group), depending on the position of the carbon atom on the benzene ring from which the hydrogen atom is removed and the position of the carbon atom on the benzene ring to which the alkylene group is bonded, A para-phenylene-alkylene group (for example, a group represented by the following formula (71a)), a meta-phenylene-alkylene group (for example, a group represented by the following formula (71b)), an ortho-phenylene-alkylene group. (For example, a group represented by the following formula (71c)).

（式中、ｒ^７は１〜５の整数を表す。）

(Wherein r ⁷ represents an integer of 1 to 5)

The group in which an arylene group and an alkylene group are bonded is preferably a group in which a phenylene group and an alkylene group are bonded (phenylene-alkylene group), more preferably a group represented by the above formula (71a), A group represented by the above formula (71b) and a group represented by the above formula (71c), more preferably a group represented by the above formula (71a) and a group represented by the above formula (71b). And particularly preferably a para-phenylene-methylene group (a group represented by the formula (71a) in which r ⁷ = 1) and a meta-phenylene-methylene group (a group represented by the formula (71b) in which r ⁷ = 1). Group, para-phenylene-ethylene group (group represented by formula (71a) where r ⁷ = 2), meta-phenylene-ethylene group (group represented by formula (71b) where r ⁷ = 2) ).

When R ⁷¹¹ is a hydrogen atom or an alkyl group, preferably m ⁷ = 1. The hydrocarbylene group for R ⁷¹² is preferably a group represented by the following formula (73), more preferably a group represented by the following formula (73a) or a group represented by the following formula (73b). Group. In the formula, ^{p 7} is an integer from 0 to 5, preferably 0 to 2 integer.

（式中、（ＣＨ_２）_ｐ７はベンゼン環上の置換基であり、ｐ^７は０〜５の整数を表し、ｐ^７が１〜５の整数である場合、（ＣＨ_２）_ｐ７が式（７１）の窒素原子と結合する。）

（式中、ｐ^７は０〜５の整数を表し、ｐ^７が１〜５の整数である場合、（ＣＨ_２）_ｐ７が式（７１）の窒素原子と結合する。）

（式中、ｐ^７は０〜５の整数を表し、ｐ^７が１〜５の整数である場合、（ＣＨ_２）_ｐ７が式（７１）の窒素原子と結合する。）

_{(Wherein, (CH 2) p7} is a substituent on the benzene ring, ^{p 7} represents an integer of 0 to 5, when ^{p 7} is an integer of 1 to _{5, (CH 2) p7} Formula ( 71) to the nitrogen atom.)

(Wherein, ^{p 7} represents an integer of 0 to 5, when ^{p 7} is an integer of 1 to _5, it is _{(CH 2) p7} binds to the nitrogen atom of formula (71).)

(Wherein, ^{p 7} represents an integer of 0 to 5, when ^{p 7} is an integer of 1 to _5, it is _{(CH 2) p7} binds to the nitrogen atom of formula (71).)

When R ⁷¹¹ is an alkenyl group and m ⁷ = 1, the hydrocarbylene group of R ⁷¹² is preferably an alkylene group, more preferably a methylene group or an ethylene group.

R ⁷¹³ and R ⁷¹⁴ are each a hydrocarbyl group, a trihydrocarbyl silyl group, or a hydrocarbylene group in which R ⁷¹³ and R ⁷¹⁴ are bonded to each other and may have a nitrogen atom and / or an oxygen atom. Alternatively, R ⁷¹³ and R ⁷¹⁴ are one group and represent a group bonded to a nitrogen atom with a double bond.

^Examples of the hydrocarbyl group for R ⁷¹³ and R ⁷¹⁴ include an alkyl group, an alkenyl group, an alkynyl group, an aryl group, and an aralkyl group. Examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, and tert-butyl group. Examples of the alkenyl group include a vinyl group, an allyl group, a 1-propenyl group, and a 1-methylethenyl group. Examples of the alkynyl group include an ethynyl group and a propargyl group. Examples of the aryl group include a phenyl group, a tolyl group, and a xylyl group. Examples of the aralkyl group include a benzyl group.

The number of carbon atoms of the hydrocarbyl group of R ⁷¹³ and R ⁷¹⁴ is preferably 1 to 10, more preferably 1 to 4.

The hydrocarbyl group of R ⁷¹³ and R ⁷¹⁴ is preferably an alkyl group or an alkenyl group, more preferably a linear alkyl group having 1 to 4 carbon atoms or an alkenyl group having 2 to 4 carbon atoms. More preferably, they are a methyl group, an ethyl group, and an allyl group.

^Examples of the trihydrocarbylsilyl group of ^R713 and ^R714 include trialkylsilyl groups such as a trimethylsilyl group, a triethylsilyl group, a triisopropylsilyl group, and a tert-butyldimethylsilyl group.

The trihydrocarbyl silyl group R ⁷¹³ and R ^714, preferably a trialkylsilyl group having a carbon number of 3 to 9, more preferably an alkyl group bonded to the silicon atoms of 1 to 3 carbon atoms It is a trialkylsilyl group which is an alkyl group.

^Examples of the hydrocarbylene group optionally having a nitrogen atom and / or an oxygen atom to which R ⁷¹³ and R ⁷¹⁴ are bonded include a hydrocarbylene group, a hydrocarbylene group having a nitrogen atom, and a hydrocarbylene having an oxygen atom. Group. Examples of the hydrocarbylene group include an alkylene group such as an ethylene group, a trimethylene group, a tetramethylene group, a pentamethylene group, and a hexamethylene group. As the hydrocarbylene group having a nitrogen atom, a group represented by —CH ₂ CH ₂ —NH—CH ₂ —, a group represented by —CH ₂ CH ₂ —N═CH—, —CH═CH—N A group represented by ═CH— and a group represented by —CH ₂ CH ₂ —NH—CH ₂ CH ₂ — can be exemplified. Examples of the hydrocarbylene group having an oxygen atom include a group represented by —CH ₂ CH ₂ —O—CH ₂ CH ₂ —.

The number of carbon atoms of the group to which R ⁷¹³ and R ⁷¹⁴ are bonded is preferably 2 to 20, more preferably 2 to 7, and still more preferably 4 to 6.

The hydrocarbylene group which may have a nitrogen atom and / or oxygen atom to which R ⁷¹³ and R ⁷¹⁴ are bonded as a hetero atom is preferably a hydrocarbylene group, more preferably an alkylene group, A polymethylene group is preferred.

Examples of one group in which R ⁷¹³ and R ⁷¹⁴ are bonded to the nitrogen atom with a double bond include ethylidene group, propylidene group, butylidene group, 1-methylethylidene group, 1-methylpropylidene group, 1,3-dimethylbutylidene And hydrocarbylidene groups such as groups.

The number of carbon atoms of one group in which R ⁷¹³ and R ⁷¹⁴ are bonded to the nitrogen atom with a double bond is preferably 2 to 20, and more preferably 2 to 6.

R ⁷¹³ and R ⁷¹⁴ are preferably a hydrocarbyl group, a trihydrocarbyl silyl group, or a hydrocarbylene group in which R ⁷¹³ and R ⁷¹⁴ are bonded, and more preferably 4 carbon atoms in which R ⁷¹³ and R ⁷¹⁴ are bonded. -6 polymethylene groups.

Examples of the compound represented by the formula (71) include the following compounds in which R ⁷¹¹ is a hydrogen atom and m ⁷ = 1.

Compound in which R ⁷¹² is a group represented by formula (73) and p ⁷ = 0:
4-N, N-dimethylaminostyrene,
3-N, N-dimethylaminostyrene,
4-N, N-diethylaminostyrene,
3-N, N-diethylaminostyrene,
4-N, N-di-n-propylaminostyrene,
3-N, N-di-n-propylaminostyrene,
4-N, N-di-n-butylaminostyrene,
3-N, N-di-n-butylaminostyrene,
4-N, N-diallylaminostyrene,
3-N, N-diallylaminostyrene,
4-N, N-bis (trimethylsilyl) aminostyrene,
3-N, N-bis (trimethylsilyl) aminostyrene,
4-N, N-bis (tert-butyldimethylsilyl) aminostyrene,
3-N, N-bis (tert-butyldimethylsilyl) aminostyrene,
4-aziridinyl styrene,
3-aziridinyl styrene,
4-pyrrolidinylstyrene,
3-pyrrolidinylstyrene,
4-piperidinylstyrene,
3-piperidinylstyrene,
4-hexamethyleneiminostyrene,
3-hexamethyleneiminostyrene.

Compound in which R ⁷¹² is a group represented by formula (73) and p ⁷ = 1:
4-N, N-dimethylaminomethylstyrene,
3-N, N-dimethylaminomethylstyrene,
4-N, N-diethylaminomethylstyrene,
3-N, N-diethylaminomethylstyrene,
4-N, N-di-n-propylaminomethylstyrene,
3-N, N-di-n-propylaminomethylstyrene,
4-N, N-di-n-butylaminomethylstyrene,
3-N, N-di-n-butylaminomethylstyrene,
4-N, N-diallylaminomethylstyrene,
3-N, N-diallylaminomethylstyrene,
4-N, N-bis (trimethylsilyl) aminomethylstyrene,
3-N, N-bis (trimethylsilyl) aminomethylstyrene,
4-N, N-bis (tert-butyldimethylsilyl) aminomethylstyrene,
3-N, N-bis (tert-butyldimethylsilyl) aminomethylstyrene,
4-aziridinylmethylstyrene,
3-aziridinylmethylstyrene,
4-pyrrolidinylmethylstyrene,
3-pyrrolidinylmethylstyrene,
4-piperidinylmethylstyrene,
3-piperidinylmethylstyrene,
4-hexamethyleneiminomethylstyrene,
3-hexamethyleneiminomethylstyrene.

Compound wherein R ⁷¹² is a group represented by formula (73) and p ⁷ = 2:
4-N, N-dimethylaminoethylstyrene,
3-N, N-dimethylaminoethylstyrene,
4-N, N-diethylaminoethylstyrene,
3-N, N-diethylaminoethylstyrene,
4-N, N-di-n-propylaminoethylstyrene,
3-N, N-di-n-propylaminoethylstyrene,
4-N, N-di-n-butylaminoethylstyrene,
3-N, N-di-n-butylaminoethylstyrene,
4-N, N-diallylaminoethylstyrene,
3-N, N-diallylaminoethylstyrene,
4-N, N-bis (trimethylsilyl) aminoethylstyrene,
3-N, N-bis (trimethylsilyl) aminoethylstyrene,
4-N, N-bis (tert-butyldimethylsilyl) aminoethylstyrene,
3-N, N-bis (tert-butyldimethylsilyl) aminoethylstyrene,
4-aziridinylethylstyrene,
3-aziridinylethylstyrene,
4-pyrrolidinylethylstyrene,
3-pyrrolidinylethylstyrene,
4-piperidinylethylstyrene,
3-piperidinylethylstyrene,
4-hexamethyleneiminoethylstyrene,
3-hexamethyleneiminoethylstyrene.

Examples of the compound represented by the formula (71) include the following compounds in which R ⁷¹¹ is a methyl group and m ⁷ = 1.

Compound in which R ⁷¹² is a group represented by formula (73) and p ⁷ = 0:
4-N, N-dimethylaminoisopropenylbenzene,
3-N, N-dimethylaminoisopropenylbenzene,
4-N, N-diethylaminoisopropenylbenzene,
3-N, N-diethylaminoisopropenylbenzene,
4-N, N-di-n-propylaminoisopropenylbenzene,
3-N, N-di-n-propylaminoisopropenylbenzene,
4-N, N-di-n-butylaminoisopropenylbenzene,
3-N, N-di-n-butylaminoisopropenylbenzene,
4-N, N-diallylaminoisopropenylbenzene,
3-N, N-diallylaminoisopropenylbenzene,
4-N, N-bis (trimethylsilyl) aminoisopropenylbenzene,
3-N, N-bis (trimethylsilyl) aminoisopropenylbenzene,
4-N, N-bis (tert-butyldimethylsilyl) aminoisopropenylbenzene,
3-N, N-bis (tert-butyldimethylsilyl) aminoisopropenylbenzene,
4-aziridinyl isopropenylbenzene,
3-aziridinyl isopropenylbenzene,
4-pyrrolidinylisopropenylbenzene,
3-pyrrolidinylisopropenylbenzene,
4-piperidinylisopropenylbenzene,
3-piperidinylisopropenylbenzene,
4-hexamethyleneiminoisopropenylbenzene,
3-hexamethyleneiminoisopropenylbenzene.

Compound in which R ⁷¹² is a group represented by formula (73) and p ⁷ = 1:
4-N, N-dimethylaminomethylisopropenylbenzene,
3-N, N-dimethylaminomethylisopropenylbenzene,
4-N, N-diethylaminomethylisopropenylbenzene,
3-N, N-diethylaminomethylisopropenylbenzene,
4-N, N-di-n-propylaminomethylisopropenylbenzene,
3-N, N-di-n-propylaminomethylisopropenylbenzene,
4-N, N-di-n-butylaminomethylisopropenylbenzene,
3-N, N-di-n-butylaminomethylisopropenylbenzene,
4-N, N-diallylaminomethylisopropenylbenzene,
3-N, N-diallylaminomethylisopropenylbenzene,
4-N, N-bis (trimethylsilyl) aminomethylisopropenylbenzene,
3-N, N-bis (trimethylsilyl) aminomethylisopropenylbenzene,
4-N, N-bis (tert-butyldimethylsilyl) aminomethylisopropenylbenzene,
3-N, N-bis (tert-butyldimethylsilyl) aminomethylisopropenylbenzene,
4-aziridinylmethyl isopropenylbenzene,
3-aziridinylmethyl isopropenylbenzene,
4-pyrrolidinylmethylisopropenylbenzene,
3-pyrrolidinylmethylisopropenylbenzene,
4-piperidinylmethylisopropenylbenzene,
3-piperidinylmethyl isopropenylbenzene,
4-hexamethyleneiminomethylisopropenylbenzene,
3-hexamethyleneiminomethylisopropenylbenzene.

Compound wherein R ⁷¹² is a group represented by formula (73) and p ⁷ = 2:
4-N, N-dimethylaminoethylisopropenylbenzene,
3-N, N-dimethylaminoethylisopropenylbenzene,
4-N, N-diethylaminoethylisopropenylbenzene,
3-N, N-diethylaminoethylisopropenylbenzene,
4-N, N-di-n-propylaminoethylisopropenylbenzene,
3-N, N-di-n-propylaminoethylisopropenylbenzene,
4-N, N-di-n-butylaminoethylisopropenylbenzene,
3-N, N-di-n-butylaminoethyl isopropenylbenzene,
4-N, N-diallylaminoethyl isopropenylbenzene,
3-N, N-diallylaminoethylisopropenylbenzene,
4-N, N-bis (trimethylsilyl) aminoethylisopropenylbenzene,
3-N, N-bis (trimethylsilyl) aminoethylisopropenylbenzene,
4-N, N-bis (tert-butyldimethylsilyl) aminoethylisopropenylbenzene,
3-N, N-bis (tert-butyldimethylsilyl) aminoethylisopropenylbenzene,
4-aziridinylethyl isopropenylbenzene,
3-aziridinylethyl isopropenylbenzene,
4-pyrrolidinylethyl isopropenylbenzene,
3-pyrrolidinylethyl isopropenylbenzene,
4-piperidinylethyl isopropenylbenzene,
3-piperidinylethyl isopropenylbenzene,
4-hexamethyleneiminoethyl isopropenylbenzene,
3-hexamethyleneiminoethyl isopropenylbenzene.

Examples of the compound represented by the formula (71) include the following compounds in which R ⁷¹¹ is a vinyl group and m ⁷ = 0.
2-N, N-dimethylamino-1,3-butadiene,
2-N, N-diethylamino-1,3-butadiene,
2-N, N-di-n-propylamino-1,3-butadiene,
2-N, N-di-n-butylamino-1,3-butadiene,
2-N, N-diallylamino-1,3-butadiene,
2-N, N-bis (trimethylsilyl) amino-1,3-butadiene,
2-N, N-bis (tert-butyldimethylsilyl) amino-1,3-butadiene,
2-aziridinyl-1,3-butadiene,
2-pyrrolidinyl-1,3-butadiene,
2-piperidinyl-1,3-butadiene,
2-Hexamethyleneimino-1,3-butadiene.

Examples of the compound represented by the formula (71) include the following compounds in which R ⁷¹¹ is a vinyl group and m ⁷ = 1.
2-N, N-dimethylaminomethyl-1,3-butadiene,
2-N, N-diethylaminomethyl-1,3-butadiene,
2-N, N-di-n-propylaminomethyl-1,3-butadiene,
2-N, N-di-n-butylaminomethyl-1,3-butadiene,
2-N, N-diallylaminomethyl-1,3-butadiene,
2-N, N-bis (trimethylsilyl) aminomethyl-1,3-butadiene,
2-N, N-bis (tert-butyldimethylsilyl) aminomethyl-1,3-butadiene,
2-aziridinylmethyl-1,3-butadiene,
2-pyrrolidinylmethyl-1,3-butadiene,
2-piperidinylmethyl-1,3-butadiene,
2-hexamethyleneiminomethyl-1,3-butadiene,
5-N, N-dimethylamino-3-methylene-1-pentene,
5-N, N-diethylamino-3-methylene-1-pentene,
5-N, N-di-n-propylamino-3-methylene-1-pentene,
5-N, N-di-n-butylamino-3-methylene-1-pentene,
5-N, N-diallylamino-3-methylene-1-pentene,
5-N, N-bis (trimethylsilyl) amino-3-methylene-1-pentene,
5-N, N-bis (tert-butyldimethylsilyl) amino-3-methylene-1-pentene,
5-aziridinyl-3-methylene-1-pentene,
5-pyrrolidinyl-3-methylene-1-pentene,
5-piperidinyl-3-methylene-1-pentene,
5-Hexamethyleneimino-3-methylene-1-pentene.

The compound represented by formula (71) is preferably a compound in which R ⁷¹¹ is a hydrogen atom and m ⁷ is 1. More ^{preferably, R 713} and ^{R 714} are each a methyl group or an ethyl group ^{compound, R 713} and ^{R 714} are compounds trimethylsilyl ^group, is bonded to the ^{R 713} and ^{R 714, R 713} and R ^In this compound, the group to which ⁷¹⁴ is bonded is a polymethylene group having 4 to 6 carbon atoms.

Compounds in which R ⁷¹³ and R ⁷¹⁴ are each a methyl group or an ethyl group:
4-N, N-dimethylaminostyrene,
3-N, N-dimethylaminostyrene,
4-N, N-diethylaminostyrene,
3-N, N-diethylaminostyrene,
4-N, N-dimethylaminomethylstyrene,
3-N, N-dimethylaminomethylstyrene,
4-N, N-diethylaminomethylstyrene,
3-N, N-diethylaminomethylstyrene,
4-N, N-dimethylaminoethylstyrene,
3-N, N-dimethylaminoethylstyrene,
4-N, N-diethylaminoethylstyrene,
3-N, N-diethylaminoethylstyrene.

Compounds in which R ⁷¹³ and R ⁷¹⁴ are trimethylsilyl groups:
4-N, N-bis (trimethylsilyl) aminostyrene,
3-N, N-bis (trimethylsilyl) aminostyrene,
4-N, N-bis (trimethylsilyl) aminomethylstyrene,
3-N, N-bis (trimethylsilyl) aminomethylstyrene,
4-N, N-bis (trimethylsilyl) aminoethylstyrene,
3-N, N-bis (trimethylsilyl) aminoethylstyrene.

The R ⁷¹³ and ^{R 714} are ^bonded, compound group and ^{R 713} and ^{R 714} are bonded is a polymethylene group of 4 to 6 carbon atoms:
4-pyrrolidinylstyrene,
3-pyrrolidinylstyrene,
4-piperidinylstyrene,
3-piperidinylstyrene,
4-hexamethyleneiminostyrene,
3-hexamethyleneiminostyrene,
4-pyrrolidinylmethylstyrene,
3-pyrrolidinylmethylstyrene,
4-piperidinylmethylstyrene,
3-piperidinylmethylstyrene,
4-hexamethyleneiminomethylstyrene,
3-hexamethyleneiminomethylstyrene,
4-pyrrolidinylethylstyrene,
3-pyrrolidinylethylstyrene,
4-piperidinylethylstyrene,
3-piperidinylethylstyrene,
4-hexamethyleneiminoethylstyrene,
3-hexamethyleneiminoethylstyrene.

The compound represented by formula (71), more ^preferably, the ^{R 713} and ^{R 714} are ^bonded, compound group and ^{R 713} and ^{R 714} are bonded is a polymethylene group of 4 to 6 carbon atoms It is.

As the compound represented by the formula (71), 4-pyrrolidinylethylstyrene and 3-pyrrolidinylethylstyrene are particularly preferable.

R ⁷²¹ , R ⁷²² and R ⁷²³ each represent a hydrocarbyl group or a hydrocarbyloxy group.

^Examples of the hydrocarbyl group for R ⁷²¹ , R ⁷²² , and R ⁷²³ include alkyl groups such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, and a tert-butyl group. be able to. The number of carbon atoms of the hydrocarbyl group is preferably 1 to 10, more preferably 1 to 3.

The hydrocarbyl group for R ⁷²¹ , R ⁷²² , and R ⁷²³ is preferably an alkyl group, more preferably an alkyl group having 1 to 10 carbon atoms, and still more preferably 1 to 3 carbon atoms. And particularly preferably a methyl group or an ethyl group.

^Examples of the hydrocarbyloxy group for R ⁷²¹ , R ⁷²² , and R ⁷²³ include alkoxy groups such as a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, a sec-butoxy group, and a tert-butoxy group; An aryloxy group such as a phenoxy group can be exemplified. The number of carbon atoms of the hydrocarbyloxy group is preferably 1 to 10, more preferably 1 to 3.

The hydrocarbyloxy group for R ⁷²¹ , R ⁷²² , and R ⁷²³ is preferably an alkoxy group, more preferably an alkoxy group having 1 to 10 carbon atoms, and still more preferably 1 to 1 carbon atom. 3 is particularly preferably a methoxy group or an ethoxy group.

At least one of R ⁷²¹ , R ⁷²² , and R ⁷²³ is a hydrocarbyloxy group, and in order to improve fuel economy, preferably at least two of R ⁷²¹ , R ⁷²² , and R ⁷²³ are hydrocarbyloxy groups, More preferably, three of R ⁷²¹ , R ⁷²² and R ⁷²³ are hydrocarbyloxy groups.

R ⁷²⁴ and R ⁷²⁵ are each a hydrocarbyl group optionally having a hydrogen atom, a nitrogen atom and / or an oxygen atom, or R ⁷²⁴ and R ⁷²⁵ are bonded to form a nitrogen atom and / or an oxygen atom. The hydrocarbylene group which may have, or ^R724 and ^R725 are one group, ^Comprising : The group couple | bonded with a nitrogen atom with a double bond is represented.

^Examples of the hydrocarbyl group of R ⁷²⁴ and R ⁷²⁵ include an alkyl group such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group; vinyl group, allyl group, Examples thereof include alkenyl groups such as 1-propenyl group and 1-methylethenyl group; alkynyl groups such as ethynyl group and propargyl group; aryl groups such as phenyl group, tolyl group and xylyl group; and aralkyl groups such as benzyl group.

^Examples of the hydrocarbyl group having a nitrogen atom of R ⁷²⁴ and R ⁷²⁵ include a dialkylaminoalkyl group such as a dimethylaminomethyl group, a dimethylaminoethyl group, a dimethylaminopropyl group, a diethylaminomethyl group, a diethylaminoethyl group, and a diethylaminopropyl group. Can do.

^Examples of the hydrocarbyl group having an oxygen atom for R ⁷²⁴ and R ⁷²⁵ include an alkoxyalkyl group such as a methoxymethyl group, a methoxyethyl group, a methoxypropyl group, an ethoxymethyl group, an ethoxyethyl group, and an ethoxypropyl group; A monooxacycloalkyl group such as an oxetanyl group or 2-tetrahydrofuranyl group; a dioxacycloalkyl group such as a 2-dioxolanyl group; an alkyl group substituted with a monooxacycloalkyl group such as a glycidyl group or a tetrahydrofurfuryl group; A 3,4-epoxycyclohexyl group can be mentioned.

In this specification, the monooxacycloalkyl group represents a group in which one CH ₂ of the cycloalkyl group is replaced with an oxygen atom. The dioxacycloalkyl group represents a group in which _two CH ₂ of the cycloalkyl group are replaced with an oxygen atom.

The number of carbon atoms of the hydrocarbyl group which may have a nitrogen atom and / or an oxygen atom of R ⁷²⁴ and R ⁷²⁵ is preferably 1 to 10, and more preferably 1 to 6.

^{Examples of} the group in which R ⁷²⁴ and R ⁷²⁵ are bonded include a hydrocarbylene group, a hydrocarbylene group having a nitrogen atom, and a hydrocarbylene group having an oxygen atom. Examples of the hydrocarbylene group include alkylene groups such as trimethylene group, tetramethylene group, pentamethylene group, and hexamethylene group. As the hydrocarbylene group having a nitrogen atom, a group represented by —CH ₂ CH ₂ —NH—CH ₂ —, a group represented by —CH ₂ CH ₂ —N═CH—, —CH═CH—N A group represented by ═CH— and a group represented by —CH ₂ CH ₂ —NH—CH ₂ CH ₂ — can be exemplified. Examples of the hydrocarbylene group having an oxygen atom include a group represented by —CH ₂ CH ₂ —O—CH ₂ CH ₂ —.

The number of carbon atoms of the group to which R ⁷²⁴ and R ⁷²⁵ are bonded is preferably 2 to 20, and more preferably 2 to 12.

Examples of one group in which R ⁷²⁴ and R ⁷²⁵ are bonded to the nitrogen atom with a double bond include ethylidene group, propylidene group, butylidene group, 1-methylethylidene group, 1-methylpropylidene group, 1,3-dimethylbutylidene A hydrocarbylidene group such as a group; 4-N, N-dimethylaminobenzylidene group and the like.

The number of carbon atoms of one group in which R ⁷²⁴ and R ⁷²⁵ are bonded to the nitrogen atom with a double bond is preferably 2 to 20, and more preferably 2 to 12.

R ⁷²⁴ and R ⁷²⁵ are preferably a hydrocarbyl group, or a hydrocarbylene group in which R ⁷²⁴ and R ⁷²⁵ are bonded, or R ⁷²⁴ and R ⁷²⁵ are one group, and a nitrogen atom Is a hydrocarbylidene group which is a group bonded by a double bond, more preferably a hydrocarbyl group, and still more preferably an alkyl group. The alkyl group is preferably a methyl group or an ethyl group.

n ⁷ is an integer of 1 to 10, preferably 2 to 4, and more preferably 3.

As a compound represented by Formula (72), as a compound in which R ⁷²⁴ and R ⁷²⁵ are alkyl groups,
[3- (dimethylamino) propyl] trimethoxysilane,
[3- (diethylamino) propyl] trimethoxysilane,
[3- (ethylmethylamino) propyl] trimethoxysilane,
[3- (dimethylamino) propyl] triethoxysilane,
[3- (diethylamino) propyl] triethoxysilane,
[3- (dialkylamino) propyl] trialkoxysilanes such as [3- (ethylmethylamino) propyl] triethoxysilane;

[3- (dimethylamino) propyl] methyldimethoxysilane,
[3- (diethylamino) propyl] methyldimethoxysilane,
[3- (ethylmethylamino) propyl] methyldimethoxysilane,
[3- (dimethylamino) propyl] ethyldimethoxysilane,
[3- (diethylamino) propyl] ethyldimethoxysilane,
[3- (ethylmethylamino) propyl] ethyldimethoxysilane,
[3- (dimethylamino) propyl] methyldiethoxysilane,
[3- (diethylamino) propyl] methyldiethoxysilane,
[3- (ethylmethylamino) propyl] methyldiethoxysilane,
[3- (dimethylamino) propyl] ethyldiethoxysilane,
[3- (diethylamino) propyl] ethyldiethoxysilane,
[3- (dialkylamino) propyl] alkyl dialkoxysilanes such as [3- (ethylmethylamino) propyl] ethyldiethoxysilane;

[3- (dimethylamino) propyl] dimethylmethoxysilane,
[3- (diethylamino) propyl] dimethylmethoxysilane,
[3- (dimethylamino) propyl] diethylmethoxysilane,
[3- (diethylamino) propyl] diethylmethoxysilane,
[3- (dimethylamino) propyl] dimethylethoxysilane,
[3- (diethylamino) propyl] dimethylethoxysilane,
[3- (dimethylamino) propyl] diethylethoxysilane,
[3- (Dialkylamino) propyl] dialkylalkoxysilanes such as [3- (diethylamino) propyl] diethylethoxysilane can be mentioned.

As the compound represented by the formula (72), as a compound in which R ⁷²⁴ and R ⁷²⁵ are alkoxyalkyl groups,
{3- [bis (methoxymethyl) amino] propyl} trimethoxysilane,
{3- [bis (ethoxymethyl) amino] propyl} trimethoxysilane,
{3- [bis (methoxyethyl) amino] propyl} trimethoxysilane,
{3- [bis (ethoxyethyl) amino] propyl} trimethoxysilane,
{3- [bis (methoxymethyl) amino] propyl} triethoxysilane,
{3- [bis (ethoxymethyl) amino] propyl} triethoxysilane,
{3- [bis (methoxyethyl) amino] propyl} triethoxysilane,
{3- [bis (alkoxyalkyl) amino] propyl} trialkoxysilanes such as {3- [bis (ethoxyethyl) amino] propyl} triethoxysilane;

{3- [bis (methoxymethyl) amino] propyl} methyldimethoxysilane,
{3- [bis (ethoxymethyl) amino] propyl} methyldimethoxysilane,
{3- [bis (methoxyethyl) amino] propyl} methyldimethoxysilane,
{3- [bis (ethoxyethyl) amino] propyl} methyldimethoxysilane,
{3- [bis (methoxymethyl) amino] propyl} ethyldimethoxysilane,
{3- [bis (ethoxymethyl) amino] propyl} ethyldimethoxysilane,
{3- [bis (methoxyethyl) amino] propyl} ethyldimethoxysilane,
{3- [bis (ethoxyethyl) amino] propyl} ethyldimethoxysilane,
{3- [bis (methoxymethyl) amino] propyl} methyldiethoxysilane,
{3- [bis (ethoxymethyl) amino] propyl} methyldiethoxysilane,
{3- [bis (methoxyethyl) amino] propyl} methyldiethoxysilane,
{3- [bis (ethoxyethyl) amino] propyl} methyldiethoxysilane,
{3- [bis (methoxymethyl) amino] propyl} ethyldiethoxysilane,
{3- [bis (ethoxymethyl) amino] propyl} ethyldiethoxysilane,
{3- [bis (methoxyethyl) amino] propyl} ethyldiethoxysilane,
{3- [bis (alkoxyalkyl) amino] propyl} alkyl dialkoxysilanes such as {3- [bis (ethoxyethyl) amino] propyl} ethyldiethoxysilane;

{3- [bis (methoxymethyl) amino] propyl} dimethylmethoxysilane,
{3- [bis (ethoxymethyl) amino] propyl} dimethylmethoxysilane,
{3- [bis (methoxyethyl) amino] propyl} dimethylmethoxysilane,
{3- [bis (ethoxyethyl) amino] propyl} dimethylmethoxysilane,
{3- [bis (methoxymethyl) amino] propyl} diethylmethoxysilane,
{3- [bis (ethoxymethyl) amino] propyl} diethylmethoxysilane,
{3- [bis (methoxyethyl) amino] propyl} diethylmethoxysilane,
{3- [bis (ethoxyethyl) amino] propyl} diethylmethoxysilane,
{3- [bis (methoxymethyl) amino] propyl} dimethylethoxysilane,
{3- [bis (ethoxymethyl) amino] propyl} dimethylethoxysilane,
{3- [bis (methoxyethyl) amino] propyl} dimethylethoxysilane,
{3- [bis (ethoxyethyl) amino] propyl} dimethylethoxysilane,
{3- [bis (methoxymethyl) amino] propyl} diethylethoxysilane,
{3- [bis (ethoxymethyl) amino] propyl} diethylethoxysilane,
{3- [bis (methoxyethyl) amino] propyl} diethylethoxysilane,
Mention may be made of {3- [bis (alkoxyalkyl) amino] propyl} dialkylalkoxysilanes such as {3- [bis (ethoxyethyl) amino] propyl} diethylethoxysilane.

As the compound represented by the formula (72), as compounds in which R ⁷²⁴ and R ⁷²⁵ are oxiranyl groups,
{3- [di (oxiranyl) amino] propyl} trimethoxysilane,
{3- [di (oxiranyl) amino] propyl} triethoxysilane,
{3- [di (oxiranyl) amino] propyl} methyldimethoxysilane,
{3- [di (oxiranyl) amino] propyl} ethyldimethoxysilane,
{3- [di (oxiranyl) amino] propyl} methyldiethoxysilane,
{3- [di (oxiranyl) amino] propyl} ethyldiethoxysilane,
{3- [di (oxiranyl) amino] propyl} dimethylmethoxysilane,
{3- [di (oxiranyl) amino] propyl} diethylmethoxysilane,
{3- [di (oxiranyl) amino] propyl} dimethylethoxysilane,
Examples include {3- [di (oxiranyl) amino] propyl} diethylethoxysilane.

As a compound represented by Formula (72), as a compound in which R ⁷²⁴ and R ⁷²⁵ are tetrahydrofuranyl groups,
{3- [di (tetrahydrofuranyl) amino] propyl} trimethoxysilane,
{3- [di (tetrahydrofuranyl) amino] propyl} triethoxysilane,
{3- [di (tetrahydrofuranyl) amino] propyl} methyldimethoxysilane,
{3- [di (tetrahydrofuranyl) amino] propyl} ethyldimethoxysilane,
{3- [di (tetrahydrofuranyl) amino] propyl} methyldiethoxysilane,
{3- [di (tetrahydrofuranyl) amino] propyl} ethyldiethoxysilane,
{3- [di (tetrahydrofuranyl) amino] propyl} dimethylmethoxysilane,
{3- [di (tetrahydrofuranyl) amino] propyl} diethylmethoxysilane,
{3- [di (tetrahydrofuranyl) amino] propyl} dimethylethoxysilane,
Examples include {3- [di (tetrahydrofuranyl) amino] propyl} diethylethoxysilane.

As a compound represented by the formula (72), as a compound in which R ⁷²⁴ and R ⁷²⁵ are glycidyl groups,
{3- [di (glycidyl) amino] propyl} trimethoxysilane,
{3- [di (glycidyl) amino] propyl} triethoxysilane,
{3- [di (glycidyl) amino] propyl} methyldimethoxysilane,
{3- [di (glycidyl) amino] propyl} ethyldimethoxysilane,
{3- [di (glycidyl) amino] propyl} methyldiethoxysilane,
{3- [di (glycidyl) amino] propyl} ethyldiethoxysilane,
{3- [di (glycidyl) amino] propyl} dimethylmethoxysilane,
{3- [di (glycidyl) amino] propyl} diethylmethoxysilane,
{3- [di (glycidyl) amino] propyl} dimethylethoxysilane,
Examples include {3- [di (glycidyl) amino] propyl} diethylethoxysilane.

As the compound represented by the formula (72), as compounds in which R ⁷²⁴ and R ⁷²⁵ are tetrahydrofurfuryl groups,
{3- [di (tetrahydrofurfuryl) amino] propyl} trimethoxysilane,
{3- [di (tetrahydrofurfuryl) amino] propyl} triethoxysilane,
{3- [di (tetrahydrofurfuryl) amino] propyl} methyldimethoxysilane,
{3- [di (tetrahydrofurfuryl) amino] propyl} ethyldimethoxysilane,
{3- [di (tetrahydrofurfuryl) amino] propyl} methyldiethoxysilane,
{3- [di (tetrahydrofurfuryl) amino] propyl} ethyldiethoxysilane,
{3- [di (tetrahydrofurfuryl) amino] propyl} dimethylmethoxysilane,
{3- [di (tetrahydrofurfuryl) amino] propyl} diethylmethoxysilane,
{3- [di (tetrahydrofurfuryl) amino] propyl} dimethylethoxysilane,
Examples include {3- [di (tetrahydrofurfuryl) amino] propyl} diethylethoxysilane.

As the compound represented by the formula (72), as a compound in which R ⁷²⁴ and R ⁷²⁵ are bonded,
3- (1-piperidinyl) propyltrimethoxysilane,
3- (1-piperidinyl) propyltriethoxysilane,
3- (1-piperidinyl) propylmethyldimethoxysilane,
3- (1-piperidinyl) propylethyldimethoxysilane,
3- (1-piperidinyl) propylmethyldiethoxysilane,
3- (1-piperidinyl) propylethyldiethoxysilane,
3- (1-hexamethyleneimino) propyltrimethoxysilane,
3- (1-hexamethyleneimino) propyltriethoxysilane,
3- (1-hexamethyleneimino) propylmethyldimethoxysilane,
3- (1-hexamethyleneimino) propylethyldimethoxysilane,
3- (1-hexamethyleneimino) propylmethyldiethoxysilane,
3- (1-hexamethyleneimino) propylethyldiethoxysilane,
3-morpholinopropyltrimethoxysilane,
3-morpholinopropyltriethoxysilane,
3-morpholinopropylmethyldimethoxysilane,
3-morpholinopropylethyldimethoxysilane,
3-morpholinopropylmethyldiethoxysilane,
There may be mentioned 3-morpholinopropylethyldiethoxysilane.

As the compound represented by the formula (72), as a compound in which R ⁷²⁴ and R ⁷²⁵ are one group bonded to a nitrogen atom by a double bond,
N- (1,3-dimethylbutylidene) -3- (trimethoxysilyl) -1-propanamine,
N- (1,3-dimethylbutylidene) -3- (triethoxysilyl) -1-propanamine can be mentioned.

The compound represented by the formula (72) is preferably [3- (dialkylamino) propyl] trialkoxysilane.
More preferably,
[3- (dimethylamino) propyl] trimethoxysilane,
[3- (diethylamino) propyl] trimethoxysilane,
[3- (dimethylamino) propyl] triethoxysilane,
[3- (diethylamino) propyl] triethoxysilane,
More preferably,
[3- (Diethylamino) propyl] trimethoxysilane.

The content of the monomer unit based on the compound represented by the formula (71) is preferably 0.01% by mass or more, based on 100% by mass of the total amount of the monomer units in the conjugated diene polymer. More preferably, it is 0.02 mass% or more, More preferably, it is 0.05 mass% or more. Moreover, in order to raise intensity | strength, Preferably it is 20 mass% or less, More preferably, it is 2 mass% or less, More preferably, it is 1 mass% or less.

The conjugated diene polymer (G) preferably has monomer units (vinyl aromatic hydrocarbon units) based on vinyl aromatic hydrocarbons in order to increase strength. Examples of the vinyl aromatic hydrocarbon include styrene, α-methylstyrene, vinyl toluene, vinyl naphthalene, divinyl benzene, trivinyl benzene, and divinyl naphthalene. Styrene is preferable.

The content of the vinyl aromatic hydrocarbon unit is 0% by mass or more (the content of the conjugated diene unit is 100% by mass or less), where the total amount of the conjugated diene unit and the vinyl aromatic hydrocarbon unit is 100% by mass. In order to increase the strength, it is preferably 10% by mass or more (the content of the conjugated diene unit is 90% by mass or less), more preferably 15% by mass or more (the content of the conjugated diene unit is 85% by mass or less). is there. In order to improve fuel economy, the content of vinyl aromatic hydrocarbon units is preferably 50% by mass or less (the content of conjugated diene units is 50% by mass or more), more preferably 45% by mass or less. (The content of the conjugated diene unit is 55% by mass or more).

The total amount of monomer units and vinyl aromatic hydrocarbon units based on the conjugated diene unit and the compound represented by the formula (71) is 100% by mass based on the total amount of monomer units in the conjugated diene polymer. In order to improve the wear resistance, the content is preferably 99.9% by mass or more, more preferably 99.95% by mass or more, and still more preferably 100% by mass.

The Mooney viscosity (ML _{1 + 4} ) of the conjugated diene polymer (G) is preferably 10 or more, more preferably 20 or more, in order to increase the strength. Moreover, in order to improve workability, Preferably it is 200 or less, More preferably, it is 150 or less. The Mooney viscosity (ML _{1 + 4} ) is measured at 100 ° C. according to JIS K6300 (1994).

The vinyl bond content of the conjugated diene polymer (G) is preferably 80 mol% or less, more preferably 70 mol% or less, in order to improve fuel efficiency, with the content of the conjugated diene unit being 100 mol%. It is. Moreover, in order to improve grip property, Preferably it is 10 mol% or more, More preferably, it is 15 mol% or more, More preferably, it is 20 mol% or more, Most preferably, it is 40 mol% or more. The vinyl bond amount is determined from the absorption intensity in the vicinity of 910 cm ^−1, which is the absorption peak of the vinyl group, by infrared spectroscopy.

The molecular weight distribution of the conjugated diene polymer (G) is preferably 1 to 5 and more preferably 1 to 2 in order to improve fuel efficiency. The molecular weight distribution is determined by measuring the number average molecular weight (Mn) and the weight average molecular weight (Mw) by gel permeation chromatography (GPC) method and dividing Mw by Mn.

Suitable method for producing a conjugated diene polymer (G), can be mentioned a production method having the following steps A ⁷ and B ^7.
(Step A ⁷ ): A monomer unit containing a conjugated diene and a compound represented by the above formula (71) is polymerized with an alkali metal catalyst in a hydrocarbon solvent, and a monomer unit based on the conjugated diene. And a step of obtaining a polymer having an alkali metal derived from an alkali metal catalyst at at least one end of a polymer chain having a monomer unit based on the compound represented by formula (71).
(Step B ⁷ ): A step of reacting the polymer obtained in Step A ⁷ with the compound represented by the above formula (72).

The alkali metal catalyst used in step A ^7, may be mentioned alkali metal, organic alkali metal compound, a complex of an alkali metal and a polar compound, such as an oligomer having an alkali metal. Examples of the alkali metal include lithium, sodium, potassium, rubidium, cesium and the like. Examples of the organic alkali metal compound include ethyl lithium, n-propyl lithium, iso-propyl lithium, n-butyl lithium, sec-butyl lithium, t-octyl lithium, n-decyl lithium, phenyl lithium, 2-naphthyl lithium, 2 -Butylphenyllithium, 4-phenylbutyllithium, cyclohexyllithium, 4-cyclopentyllithium, dimethylaminopropyllithium, diethylaminopropyllithium, t-butyldimethylsiloxypropyllithium, N-morpholinopropyllithium, lithium hexamethyleneimide, lithium pyrrole Zido, lithium piperidide, lithium heptamethylene imide, lithium dodecamethylene imide, 1,4-dilithio-2-butene, sodium naphthalenide, sodium Bifenirido, such as potassium napthalenide can be mentioned. Examples of the complex of the alkali metal and the polar compound include potassium-tetrahydrofuran complex and potassium-diethoxyethane complex, and the oligomer having the alkali metal includes sodium salt of α-methylstyrene tetramer. I can give you. An organic lithium compound or an organic sodium compound is preferable, and an organic lithium compound having 2 to 20 carbon atoms or an organic sodium compound having 2 to 20 carbon atoms is more preferable.

Hydrocarbon solvents used in step A ⁷ is a solvent that does not deactivate the organic alkali metal compound catalyst may be mentioned aliphatic hydrocarbons, aromatic hydrocarbons, and alicyclic hydrocarbons. Examples of the aliphatic hydrocarbon include propane, n-butane, iso-butane, n-pentane, iso-pentane, n-hexane, propene, 1-butene, iso-butene, trans-2-butene, cis-2- Examples include butene, 1-pentene, 2-pentene, 1-hexene, 2-hexene and the like. Examples of the aromatic hydrocarbon include benzene, toluene, xylene, and ethylbenzene. Examples of the alicyclic hydrocarbon include cyclopentane and cyclohexane. One or more of these may be used, and the hydrocarbon solvent may be a mixture of various components such as industrial hexane. Preferably, it is a hydrocarbon having 2 to 12 carbon atoms.

In Step A ^7, a hydrocarbon solvent, an alkali with a metal catalyst, a conjugated diene, by polymerizing a monomer component containing a compound represented by the formula (71), a monomer unit derived from the conjugated diene, the A polymer having a monomer unit based on the compound represented by the formula (71) is produced. Examples of the conjugated diene include 1,3-butadiene, isoprene, 1,3-pentadiene, 2,3-dimethyl-1,3-butadiene, and 1,3-hexadiene. One or more of these are used. 1,3-butadiene and isoprene are preferred.

The amount of the compound represented by the formula (71) is preferably 0.01% by mass or more in order to improve the fuel efficiency by setting the total amount of the monomer components used in the polymerization to 100% by mass. More preferably, it is 0.02 mass% or more, More preferably, it is 0.05 mass% or more. In order to increase the strength, it is preferably 20% by mass or less, more preferably 2% by mass or less, still more preferably 1% by mass or less, and particularly preferably 0.5% by mass or less.

In Step A ^7, as a monomer, a compound represented by the conjugated diene of formula (71) may be carried out polymerization by combining vinyl aromatic hydrocarbon, the vinyl aromatic hydrocarbon include styrene, α-methylstyrene, vinyltoluene, vinylnaphthalene, divinylbenzene, trivinylbenzene, divinylnaphthalene and the like can be mentioned. Styrene is preferable.

The amount of vinyl aromatic hydrocarbon used is 0% by mass or more (the amount of conjugated diene used is 100% by mass or less), where the total amount of conjugated diene and vinyl aromatic hydrocarbon is 100% by mass. In order to increase it, it is preferably 10% by mass or more (the amount of conjugated diene used is 90% by mass or less), more preferably 15% by mass or more (the amount of conjugated diene used is 85% by mass or less). In order to improve fuel efficiency, the amount of vinyl aromatic hydrocarbon used is preferably 50% by mass or less (the amount of conjugated diene used is 50% by mass or more), more preferably 45% by mass or less (conjugated). The amount of diene used is 55% by mass or more).

In the polymerization, the total amount of the conjugated diene, the compound represented by the formula (71), and the vinyl aromatic hydrocarbon is preferably set so that the total amount of the monomers used is 100% by mass and the strength is increased. Is 99.9% by mass or more, more preferably 99.95% by mass or more, and still more preferably 100% by mass.

Polymerization step A ⁷ is agent for adjusting the vinyl bond content of the conjugated diene unit, to adjust the distribution of the monomer unit based on a monomer other than the conjugated diene unit and a conjugated diene in the conjugated diene polymer chains in It may be carried out in the presence of an agent (hereinafter collectively referred to as “regulator”). Examples of such a regulator include ether compounds, tertiary amines, and phosphine compounds. Examples of the ether compound include cyclic ethers such as tetrahydrofuran, tetrahydropyran, and 1,4-dioxane; aliphatic monoethers such as diethyl ether and dibutyl ether; ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, and diethylene glycol diethyl ether. And aliphatic ethers such as diethylene glycol dibutyl ether; aromatic ethers such as diphenyl ether and anisole. Examples of the tertiary amine include triethylamine, tripropylamine, tributylamine, N, N, N ′, N′-tetramethylethylenediamine, N, N-diethylaniline, pyridine, quinoline and the like. Examples of the phosphine compound include trimethylphosphine, triethylphosphine, triphenylphosphine, and the like. One or more of these are used.

The polymerization temperature in step ^{A 7} is usually 25 to 100 ° C., preferably from 35 to 90 ° C., more preferably from 50 to 80 ° C.. The polymerization time is usually 10 minutes to 5 hours.

In Step B ^7, the amount of the compound represented by formula to be reacted with the polymer prepared in Step A ⁷ (72) is an alkali metal per mole derived from the organic alkali metal catalyst, usually 0.1 to 3 moles Preferably, it is 0.5-2 mol, More preferably, it is 0.7-1.5 mol.

In Step ^{B 7,} the temperature of reacting the compound represented by the polymer and Formula prepared in Step ^{A 7} (72) is usually 25 to 100 ° C., preferably from 35 to 90 ° C., and more preferably Is 50-80 ° C. The reaction time is usually 60 seconds to 5 hours, preferably 5 minutes to 1 hour, more preferably 15 minutes to 1 hour.

（式中、Ｒ^８１１は水素原子又はヒドロカルビル基を表し、ｍ^８は０又は１であり、Ｒ^８１２はヒドロカルビレン基を表し、Ｔ^８０１は含窒素複素環基を表す。）

（式中、ｎ^８は１〜１０の整数を表し、Ｒ^８２１、Ｒ^８２２及びＲ^８２３は、それぞれ、ヒドロカルビル基又はヒドロカルビルオキシ基を表し、Ｒ^８２１、Ｒ^８２２及びＲ^８２３の少なくとも１つがヒドロカルビルオキシ基であり、Ｒ^８２４及びＲ^８２５は、それぞれ、水素原子、窒素原子及び／又は酸素原子を有していてもよいヒドロカルビル基、あるいは、Ｒ^８２４とＲ^８２５とが結合して、窒素原子及び／又は酸素原子を有していてもよいヒドロカルビレン基、又は、Ｒ^８２４とＲ^８２５は１つの基であって、窒素原子に二重結合で結合する基を表す。） The conjugated diene polymer (H) according to the eighth aspect of the present invention is a conjugated diene polymer having a monomer unit based on a conjugated diene and a monomer unit based on a compound represented by the following formula (81). It is obtained by reacting one end of the compound represented by the following formula (82).

(In the formula, R ⁸¹¹ represents a hydrogen atom or a hydrocarbyl group, m ⁸ is 0 or 1, R ⁸¹² represents a hydrocarbylene group, and T ⁸⁰¹ represents a nitrogen-containing heterocyclic group.)

(In the formula, n ⁸ represents an integer of 1 to 10, R ⁸²¹ , R ⁸²² and R ⁸²³ each represents a hydrocarbyl group or a hydrocarbyloxy group, and at least one of R ⁸²¹ , R ⁸²² and R ⁸²³ is hydrocarbyloxy. Each of R ⁸²⁴ and R ⁸²⁵ is a hydrocarbyl group optionally having a hydrogen atom, a nitrogen atom and / or an oxygen atom, or a combination of R ⁸²⁴ and R ⁸²⁵ to form a nitrogen atom and / Or a hydrocarbylene group which may have an oxygen atom, or R ⁸²⁴ and R ⁸²⁵ are one group and represent a group bonded to a nitrogen atom by a double bond.)

As used herein, a hydrocarbyl group represents a hydrocarbon residue. The hydrocarbyloxy group represents a group in which a hydrogen atom of a hydroxyl group is substituted with a hydrocarbyl group. The hydrocarbylene group represents a divalent hydrocarbon residue. The nitrogen-containing heterocyclic group represents a group obtained by removing one hydrogen atom from a carbon atom of a heterocyclic ring of a compound having a nitrogen-containing heterocyclic ring. In addition, a nitrogen-containing heterocyclic ring represents the heterocyclic ring which has a nitrogen atom as a hetero atom which comprises a ring.

Examples of the conjugated diene include 1,3-butadiene, isoprene, 1,3-pentadiene, 2,3-dimethyl-1,3-butadiene, 1,3-hexadiene and the like, and one or more of these are used. . The conjugated diene is preferably 1,3-butadiene or isoprene.

R ⁸¹¹ represents a hydrogen atom or a hydrocarbyl group.

^Examples of the hydrocarbyl group for R ⁸¹¹ include an alkyl group and an alkenyl group. Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, and a tert-butyl group, and a methyl group is preferable. Examples of the alkenyl group include a vinyl group, an allyl group, a 1-propenyl group, and a 1-methylethenyl group, and a vinyl group is preferable.

R ⁸¹¹ is preferably a hydrogen atom, a methyl group, or a vinyl group.

^Examples of the hydrocarbylene group for R812 include an alkylene group, an arylene group, and a group in which an arylene group and an alkylene group are bonded.

Examples of the alkylene group include a methylene group, an ethylene group, and a trimethylene group. Preferably, it is a methylene group or an ethylene group.

Examples of the arylene group include a phenylene group, a naphthylene group, and a biphenylene group. A phenylene group is preferred.

Examples of the group in which an arylene group and an alkylene group are bonded include a group in which a phenylene group and an alkylene group are bonded, a group in which a naphthylene group and an alkylene group are bonded, and a group in which a biphenylene group and an alkylene group are bonded. . A group in which a phenylene group and an alkylene group are bonded is preferable.

In addition, as the group in which the arylene group and the alkylene group are bonded, it is preferable that the carbon atom of the arylene group of the group is bonded to the carbon atom to which R ⁸¹¹ of the formula (81) is bonded.

In a group in which a phenylene group and an alkylene group are bonded (phenylene-alkylene group), depending on the position of the carbon atom on the benzene ring from which the hydrogen atom is removed and the position of the carbon atom on the benzene ring to which the alkylene group is bonded, A para-phenylene-alkylene group (for example, a group represented by the following formula (81a)), a meta-phenylene-alkylene group (for example, a group represented by the following formula (81b)), an ortho-phenylene-alkylene group. (For example, a group represented by the following formula (81c)).

（式中、ｒ^８は１〜５の整数を表す。）

(Wherein r ⁸ represents an integer of 1 to 5)

The group in which an arylene group and an alkylene group are bonded is preferably a group in which a phenylene group and an alkylene group are bonded (phenylene-alkylene group), more preferably a group represented by the above formula (81a), A group represented by the above formula (81b), a group represented by the above formula (81c), more preferably a group represented by the above formula (81a) and a group represented by the above formula (81b). And particularly preferably a para-phenylene-methylene group (a group represented by the formula (81a) in which r ⁸ = 1) and a meta-phenylene-methylene group (a group represented by the formula (81b) in which r ⁸ = 1). Group), para-phenylene-ethylene group (group represented by formula (81a) where r ⁸ = 2), meta-phenylene-ethylene group (group represented by formula (81b) where r ⁸ = 2) ).

Examples of the nitrogen-containing heterocyclic group T ^801, may be mentioned nitrogen-containing alicyclic heterocyclic group, a nitrogen-containing aromatic heterocyclic group.

The nitrogen-containing alicyclic heterocyclic group of T ⁸⁰¹ includes a group having only a nitrogen atom as a hetero atom constituting the ring, a group having a nitrogen atom and an oxygen atom as the hetero atom constituting the ring, and a hetero atom constituting the ring Examples thereof include a group having a nitrogen atom and a sulfur atom.

The nitrogen-containing alicyclic heterocyclic group having only a nitrogen atom as a hetero atom constituting the ring includes a group having an aziridine ring, a group having an azetidine ring, a group having a pyrrolidine ring, a group having a piperidine ring, hexamethyleneimine Examples thereof include a group having a ring, a group having an imidazolidine ring, a group having a piperazine ring, and a group having a pyrazolidine ring.

Examples of the group having an aziridine ring include an N-alkyl-2-aziridinyl group.
Examples of the group having an azetidine ring include an N-alkyl-2-azetidinyl group and an N-alkyl-3-azetidinyl group.
Examples of the group having a pyrrolidine ring include an N-alkyl-2-pyrrolidinyl group and an N-alkyl-3-pyrrolidinyl group.
Examples of the group having a piperidine ring include an N-alkyl-2-piperidinyl group, an N-alkyl-3-piperidinyl group, and an N-alkyl-4-piperidinyl group.
Examples of the group having a hexamethyleneimine ring include an N-alkyl-2-hexamethyleneimino group, an N-alkyl-3-hexamethyleneimino group, and an N-alkyl-4-hexamethyleneimino group.
Examples of the group having an imidazolidine ring include a 1,3-dialkyl-2-imidazolidyl group and a 1,3-dialkyl-4-imidazolidyl group.
Examples of the group having a piperazine ring include a 1,4-dialkyl-2-piperazinyl group.
Examples of the group having a pyrazolidine ring include a 1,2-dialkyl-3-pyrazolidyl group and a 1,2-dialkyl-4-pyrazolidyl group.

Examples of the nitrogen-containing alicyclic heterocyclic group having a nitrogen atom and an oxygen atom as a hetero atom constituting the ring include a group having a morpholine ring and a group having an isoxazolidine ring.

Examples of the group having a morpholine ring include an N-alkyl-2-morpholino group and an N-alkyl-3-morpholino group.
Examples of the group having an isoxazolidine ring include an N-alkyl-3-isoxazolidinyl group, an N-alkyl-4-isoxazolidinyl group, and an N-alkyl-5-isoxazolidinyl group. Can do.

Examples of the nitrogen-containing alicyclic heterocyclic group having a nitrogen atom and a sulfur atom as hetero atoms constituting the ring include a group having a thiomorpholine ring and a group having an isothiazolidine ring.

Examples of the group having a thiomorpholine ring include an N-alkyl-2-thiomorpholino group and an N-alkyl-3-thiomorpholino group.
Examples of the group having an isothiazolidine ring include an N-alkyl-3-isothiazolidinyl group, an N-alkyl-4-isothiazolidinyl group, and an N-alkyl-5-isothiazolidinyl group.

As the nitrogen-containing aromatic heterocyclic group of T ⁸⁰¹ , a group having only a nitrogen atom as a hetero atom constituting a ring, a group having a nitrogen atom and an oxygen atom as a hetero atom constituting a ring, and a hetero atom constituting a ring Examples thereof include a group having a nitrogen atom and a sulfur atom.

The nitrogen-containing aromatic heterocyclic group having only a nitrogen atom as a hetero atom constituting the ring includes a group having a pyrrole ring, a group having an imidazole ring, a group having a pyrazole ring, a group having a pyridine ring, and a pyridazine ring. A group having a pyrimidine ring, a group having a pyrazine ring, a group having a quinoline ring, a group having an isoquinoline ring, a group having a cinnoline ring, a group having a quinazoline ring, a group having a phthalazine ring, and the like.

Examples of the group having a pyrrole ring include a 2-pyrrolyl group, a 3-pyrrolyl group, a 2- (N-methylpyrrolyl) group, and a 3- (N-methylpyrrolyl) group.
Examples of the group having an imidazole ring include 2-imidazolyl group, 4-imidazolyl group, 5-imidazolyl group, 2- (N-methylimidazolyl) group, 4- (N-methylimidazolyl) group, and 5- (N-methylimidazolyl). ) Group.
Examples of the group having a pyrazole ring include 3-pyrazolyl group, 4-pyrazolyl group, 5-pyrazolyl group, 3- (N-methylpyrazolyl) group, 4- (N-methylpyrazolyl) group, and 5- (N-methylpyrazolyl). ) Group.
Examples of the group having a pyridine ring include a 2-pyridyl group, a 3-pyridyl group, and a 4-pyridyl group.
Examples of the group having a pyridazine ring include a 3-pyridazyl group and a 4-pyridazyl group.
Examples of the group having a pyrimidine ring include a 2-pyrimidyl group, a 4-pyrimidyl group, and a 5-pyrimidyl group.
Examples of the group having a pyrazine ring include a 2-pyrazyl group.
Examples of the group having a quinoline ring include a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 5-quinolyl group, a 6-quinolyl group, a 7-quinolyl group, and an 8-quinolyl group.
Examples of the group having an isoquinoline ring include a 1-isoquinolyl group, a 3-isoquinolyl group, a 4-isoquinolyl group, a 5-isoquinolyl group, a 6-isoquinolyl group, a 7-isoquinolyl group, and an 8-isoquinolyl group.
Examples of the group having a cinnoline ring include a 3-cinnolinyl group, a 4-cinnolinyl group, a 5-cinnolinyl group, a 6-cinnolinyl group, a 7-cinnolinyl group, and an 8-cinnolinyl group.
Examples of the group having a quinazoline ring include a 2-quinazolinyl group, a 4-quinazolinyl group, a 5-quinazolinyl group, a 6-quinazolinyl group, a 7-quinazolinyl group, and an 8-quinazolinyl group.
Examples of the group having a phthalazine ring include a 1-phthalazinyl group, a 5-phthalazinyl group, and a 6-phthalazinyl group.
The nitrogen-containing aromatic heterocyclic group having only a nitrogen atom as a hetero atom constituting the ring is preferably a group having an imidazole ring, a group having a pyridine ring, or a group having a quinoline ring.

Examples of the nitrogen-containing aromatic heterocyclic group having a nitrogen atom and an oxygen atom as a hetero atom constituting the ring include a group having an oxazole ring and a group having an isoxazole ring.

Examples of the group having an oxazole ring include a 2-oxazolyl group, a 4-oxazolyl group, and a 5-oxazolyl group.
Examples of the group having an isoxazole ring include a 3-isoxazolyl group, a 4-isoxazolyl group, and a 5-isoxazolyl group.
The nitrogen-containing aromatic heterocyclic group having a nitrogen atom and an oxygen atom as hetero atoms constituting the ring is preferably a group having an oxazole ring.

Examples of the nitrogen-containing aromatic heterocyclic group having a nitrogen atom and a sulfur atom as the hetero atoms constituting the ring include a group having a thiazole ring, a group having an isothiazole ring, and the like.

Examples of the group having a thiazole ring include a 2-thiazolyl group, a 4-thiazolyl group, and a 5-thiazolyl group.
Examples of the group having an isothiazole ring include a 3-isothiazolyl group, a 4-isothiazolyl group, and a 5-isothiazolyl group.
The nitrogen-containing aromatic heterocyclic group having a nitrogen atom and a sulfur atom as a hetero atom constituting the ring is preferably a group having a thiazole ring.

The nitrogen-containing heterocyclic group represented by T ⁸⁰¹ is preferably a nitrogen-containing aromatic heterocyclic group, more preferably a nitrogen-containing aromatic heterocyclic group having only a nitrogen atom as a hetero atom constituting the ring, More preferred are a group having an imidazole ring, a group having a pyridine ring, and a group having a quinoline ring, and particularly preferred is a group having a pyridine ring.

As the compound represented by the formula (81), a compound in which R ⁸¹¹ is a hydrogen atom,
1-vinylimidazole,
N-methyl-2-vinylimidazole,
N-methyl-4-vinylimidazole,
N-methyl-5-vinylimidazole,
2-vinylpyridine,
3-vinylpyridine,
4-vinylpyridine,
2-vinylquinoline,
3-vinyl quinoline,
4-vinylquinoline can be mentioned.

As the compound represented by the formula (81), a compound in which R ⁸¹¹ is a methyl group,
1-isopropenylimidazole,
N-methyl-2-isopropenylimidazole,
N-methyl-4-isopropenylimidazole,
N-methyl-5-isopropenylimidazole,
2-isopropenyl pyridine,
3-isopropenyl pyridine,
4-isopropenyl pyridine,
2-isopropenyl quinoline,
3-isopropenyl quinoline,
4-Isopropenylquinoline can be mentioned.

As the compound represented by the formula (81), as a compound in which R ⁸¹¹ is a vinyl group,
N-methyl-2- (1-methylene-2-propenyl) aziridine,
N-methyl-2- (1-methylene-2-propenyl) pyrrolidine,
N-methyl-3- (1-methylene-2-propenyl) pyrrolidine,
N-methyl-2- (1-methylene-2-propenyl) hexamethyleneimine,
N-methyl-3- (1-methylene-2-propenyl) hexamethyleneimine,
N-methyl-4- (1-methylene-2-propenyl) hexamethyleneimine,
1- (1-methylene-2-propenyl) imidazole,
N-methyl-2- (1-methylene-2-propenyl) imidazole,
N-methyl-4- (1-methylene-2-propenyl) imidazole,
N-methyl-5- (1-methylene-2-propenyl) imidazole,
2- (1-methylene-2-propenyl) pyridine,
3- (1-methylene-2-propenyl) pyridine,
4- (1-methylene-2-propenyl) pyridine,
2- (1-methylene-2-propenyl) quinoline,
3- (1-methylene-2-propenyl) quinoline,
4- (1-methylene-2-propenyl) quinoline can be mentioned.

The compound represented by the formula (81) is preferably a compound in which R ⁸¹¹ is a hydrogen atom and T ⁸⁰¹ is a group having a pyridine ring, and more preferably, R ⁸¹¹ is a hydrogen atom. ^A compound in which ⁸⁰¹ is a pyridyl group, more preferably 4-vinylpyridine.

R ⁸²¹ , R ⁸²² and R ⁸²³ each represent a hydrocarbyl group or a hydrocarbyloxy group.

^Examples of the hydrocarbyl group of R ⁸²¹ , R ⁸²² and R ⁸²³ include alkyl groups such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group and a tert-butyl group. Can do. The number of carbon atoms of the hydrocarbyl group is preferably 1 to 10, more preferably 1 to 3.

The hydrocarbyl group of R ⁸²¹ , R ⁸²² and R ⁸²³ is preferably an alkyl group, more preferably an alkyl group having 1 to 10 carbon atoms, and still more preferably 1 to 3 carbon atoms. An alkyl group, particularly preferably a methyl group or an ethyl group.

^Examples of the hydrocarbyloxy group of R ⁸²¹ , R ⁸²² and R ⁸²³ include alkoxy groups such as methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, sec-butoxy group and tert-butoxy group; An aryloxy group such as a group can be mentioned. The number of carbon atoms of the hydrocarbyloxy group is preferably 1 to 10, more preferably 1 to 3.

The hydrocarbyloxy group for R ⁸²¹ , R ⁸²² and R ⁸²³ is preferably an alkoxy group, more preferably an alkoxy group having 1 to 10 carbon atoms, and still more preferably 1 to 3 carbon atoms. And particularly preferably a methoxy group or an ethoxy group.

At least one of R ⁸²¹ , R ⁸²² and R ⁸²³ is a hydrocarbyloxy group, and in order to improve fuel efficiency, preferably at least two of R ⁸²¹ , R ⁸²² and R ⁸²³ are hydrocarbyloxy groups, more preferably In the ^formula , three of R ⁸²¹ , R ⁸²² and R ⁸²³ are hydrocarbyloxy groups.

R ⁸²⁴ and R ⁸²⁵ each have a hydrogen atom, a nitrogen atom and / or an oxygen atom, or a hydrocarbyl group which may have a hydrogen atom, or R ⁸²⁴ and R ⁸²⁵ are bonded to each other to form a nitrogen atom and / or an oxygen atom. The hydrocarbylene group which may have, or ^R824 and ^R825 are one group, ^Comprising : The group couple | bonded with a nitrogen atom with a double bond is represented.

In this specification, the hydrocarbyl group having an X atom represents a group having a structure in which a hydrogen atom and / or a carbon atom of the hydrocarbyl group is replaced with an X atom, and the hydrocarbylene group having an X atom is a hydrocarbyl group. This represents a group having a structure in which a hydrogen atom and / or a carbon atom of a len group is replaced with an X atom. For example, examples of the group having a nitrogen atom include a group having a structure in which CH is replaced by N. Examples of the group having an oxygen atom include a group having a structure in which CH ₂ is replaced with O, and a group having a structure in which two hydrogen atoms are replaced with O.

^Examples of the hydrocarbyl group of R ⁸²⁴ and R ⁸²⁵ include alkyl groups such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group; vinyl group, allyl group, Examples thereof include alkenyl groups such as 1-propenyl group and 1-methylethenyl group; alkynyl groups such as ethynyl group and propargyl group; aryl groups such as phenyl group, tolyl group and xylyl group; and aralkyl groups such as benzyl group.

Examples of the hydrocarbyl group having a nitrogen atom of R ⁸²⁴ and R ^825, dimethylaminomethyl group, dimethylaminoethyl group, dimethylaminopropyl group, diethylaminomethyl group, diethylaminoethyl group, be mentioned dialkylaminoalkyl groups such as diethylaminopropyl group Can do.

^Examples of the hydrocarbyl group having an oxygen atom of R ⁸²⁴ and R ⁸²⁵ include alkoxyalkyl groups such as a methoxymethyl group, a methoxyethyl group, a methoxypropyl group, an ethoxymethyl group, an ethoxyethyl group, and an ethoxypropyl group; a 2-oxiranyl group, 2 A monooxacycloalkyl group such as an oxetanyl group or 2-tetrahydrofuranyl group; a dioxacycloalkyl group such as a 2-dioxolanyl group; an alkyl group substituted with a monooxacycloalkyl group such as a glycidyl group or a tetrahydrofurfuryl group; A 3,4-epoxycyclohexyl group can be mentioned.

In this specification, the monooxacycloalkyl group represents a group in which one CH ₂ of the cycloalkyl group is replaced with an oxygen atom. The dioxacycloalkyl group represents a group in which _two CH ₂ of the cycloalkyl group are replaced with an oxygen atom.

The number of carbon atoms of the hydrocarbyl group which may have a nitrogen atom and / or an oxygen atom of R ⁸²⁴ and R ⁸²⁵ is preferably 1 to 10, more preferably 1 to 6.

^{Examples of} the group in which R ⁸²⁴ and R ⁸²⁵ are bonded include a hydrocarbylene group, a hydrocarbylene group having a nitrogen atom, and a hydrocarbylene group having an oxygen atom. Examples of the hydrocarbylene group include alkylene groups such as trimethylene group, tetramethylene group, pentamethylene group, and hexamethylene group. As the hydrocarbylene group having a nitrogen atom, a group represented by —CH ₂ CH ₂ —NH—CH ₂ —, a group represented by —CH ₂ CH ₂ —N═CH—, —CH═CH—N A group represented by ═CH— and a group represented by —CH ₂ CH ₂ —NH—CH ₂ CH ₂ — can be exemplified. Examples of the hydrocarbylene group having an oxygen atom include a group represented by —CH ₂ CH ₂ —O—CH ₂ CH ₂ —.

The number of carbon atoms of the group to which R ⁸²⁴ and R ⁸²⁵ are bonded is preferably 2 to 20, and more preferably 2 to 12.

One group in which R ⁸²⁴ and R ⁸²⁵ are bonded to the nitrogen atom with a double bond is an ethylidene group, a propylidene group, a butylidene group, a 1-methylethylidene group, a 1-methylpropylidene group, or 1,3-dimethylbutylidene. A hydrocarbylidene group such as a group; 4-N, N-dimethylaminobenzylidene group and the like.

The number of carbon atoms of one group in which R ⁸²⁴ and R ⁸²⁵ are bonded to the nitrogen atom with a double bond is preferably 2 to 20, and more preferably 2 to 12.

R ⁸²⁴ and R ⁸²⁵ are preferably a hydrocarbyl group, or a hydrocarbylene group in which R ⁸²⁴ and R ⁸²⁵ are bonded, or R ⁸²⁴ and R ⁸²⁵ are one group, and a nitrogen atom Is a hydrocarbylidene group which is a group bonded by a double bond, more preferably a hydrocarbyl group, and still more preferably an alkyl group. The alkyl group is preferably a methyl group or an ethyl group.

n ⁸ is an integer of from 1 to 10, preferably 2 to 4, more preferably 3.

As the compound represented by the formula (82), as compounds in which R ⁸²⁴ and R ⁸²⁵ are alkyl groups,
[3- (dimethylamino) propyl] trimethoxysilane,
[3- (diethylamino) propyl] trimethoxysilane,
[3- (ethylmethylamino) propyl] trimethoxysilane,
[3- (dimethylamino) propyl] triethoxysilane,
[3- (diethylamino) propyl] triethoxysilane,
[3- (dialkylamino) propyl] trialkoxysilanes such as [3- (ethylmethylamino) propyl] triethoxysilane;

[3- (dimethylamino) propyl] methyldimethoxysilane,
[3- (diethylamino) propyl] methyldimethoxysilane,
[3- (ethylmethylamino) propyl] methyldimethoxysilane,
[3- (dimethylamino) propyl] ethyldimethoxysilane,
[3- (diethylamino) propyl] ethyldimethoxysilane,
[3- (ethylmethylamino) propyl] ethyldimethoxysilane,
[3- (dimethylamino) propyl] methyldiethoxysilane,
[3- (diethylamino) propyl] methyldiethoxysilane,
[3- (ethylmethylamino) propyl] methyldiethoxysilane,
[3- (dimethylamino) propyl] ethyldiethoxysilane,
[3- (diethylamino) propyl] ethyldiethoxysilane,
[3- (dialkylamino) propyl] alkyl dialkoxysilanes such as [3- (ethylmethylamino) propyl] ethyldiethoxysilane;

[3- (dimethylamino) propyl] dimethylmethoxysilane,
[3- (diethylamino) propyl] dimethylmethoxysilane,
[3- (dimethylamino) propyl] diethylmethoxysilane,
[3- (diethylamino) propyl] diethylmethoxysilane,
[3- (dimethylamino) propyl] dimethylethoxysilane,
[3- (diethylamino) propyl] dimethylethoxysilane,
[3- (dimethylamino) propyl] diethylethoxysilane,
[3- (Dialkylamino) propyl] dialkylalkoxysilanes such as [3- (diethylamino) propyl] diethylethoxysilane can be mentioned.

As the compound represented by the formula (82), as a compound in which R ⁸²⁴ and R ⁸²⁵ are alkoxyalkyl groups,
{3- [bis (methoxymethyl) amino] propyl} trimethoxysilane,
{3- [bis (ethoxymethyl) amino] propyl} trimethoxysilane,
{3- [bis (methoxyethyl) amino] propyl} trimethoxysilane,
{3- [bis (ethoxyethyl) amino] propyl} trimethoxysilane,
{3- [bis (methoxymethyl) amino] propyl} triethoxysilane,
{3- [bis (ethoxymethyl) amino] propyl} triethoxysilane,
{3- [bis (methoxyethyl) amino] propyl} triethoxysilane,
{3- [bis (alkoxyalkyl) amino] propyl} trialkoxysilanes such as {3- [bis (ethoxyethyl) amino] propyl} triethoxysilane;

{3- [bis (methoxymethyl) amino] propyl} methyldimethoxysilane,
{3- [bis (ethoxymethyl) amino] propyl} methyldimethoxysilane,
{3- [bis (methoxyethyl) amino] propyl} methyldimethoxysilane,
{3- [bis (ethoxyethyl) amino] propyl} methyldimethoxysilane,
{3- [bis (methoxymethyl) amino] propyl} ethyldimethoxysilane,
{3- [bis (ethoxymethyl) amino] propyl} ethyldimethoxysilane,
{3- [bis (methoxyethyl) amino] propyl} ethyldimethoxysilane,
{3- [bis (ethoxyethyl) amino] propyl} ethyldimethoxysilane,
{3- [bis (methoxymethyl) amino] propyl} methyldiethoxysilane,
{3- [bis (ethoxymethyl) amino] propyl} methyldiethoxysilane,
{3- [bis (methoxyethyl) amino] propyl} methyldiethoxysilane,
{3- [bis (ethoxyethyl) amino] propyl} methyldiethoxysilane,
{3- [bis (methoxymethyl) amino] propyl} ethyldiethoxysilane,
{3- [bis (ethoxymethyl) amino] propyl} ethyldiethoxysilane,
{3- [bis (methoxyethyl) amino] propyl} ethyldiethoxysilane,
{3- [bis (alkoxyalkyl) amino] propyl} alkyl dialkoxysilanes such as {3- [bis (ethoxyethyl) amino] propyl} ethyldiethoxysilane;

{3- [bis (methoxymethyl) amino] propyl} dimethylmethoxysilane,
{3- [bis (ethoxymethyl) amino] propyl} dimethylmethoxysilane,
{3- [bis (methoxyethyl) amino] propyl} dimethylmethoxysilane,
{3- [bis (ethoxyethyl) amino] propyl} dimethylmethoxysilane,
{3- [bis (methoxymethyl) amino] propyl} diethylmethoxysilane,
{3- [bis (ethoxymethyl) amino] propyl} diethylmethoxysilane,
{3- [bis (methoxyethyl) amino] propyl} diethylmethoxysilane,
{3- [bis (ethoxyethyl) amino] propyl} diethylmethoxysilane,
{3- [bis (methoxymethyl) amino] propyl} dimethylethoxysilane,
{3- [bis (ethoxymethyl) amino] propyl} dimethylethoxysilane,
{3- [bis (methoxyethyl) amino] propyl} dimethylethoxysilane,
{3- [bis (ethoxyethyl) amino] propyl} dimethylethoxysilane,
{3- [bis (methoxymethyl) amino] propyl} diethylethoxysilane,
{3- [bis (ethoxymethyl) amino] propyl} diethylethoxysilane,
{3- [bis (methoxyethyl) amino] propyl} diethylethoxysilane,
Mention may be made of {3- [bis (alkoxyalkyl) amino] propyl} dialkylalkoxysilanes such as {3- [bis (ethoxyethyl) amino] propyl} diethylethoxysilane.

As the compound represented by the formula (82), as compounds in which R ⁸²⁴ and R ⁸²⁵ are oxiranyl groups,
{3- [di (oxiranyl) amino] propyl} trimethoxysilane,
{3- [di (oxiranyl) amino] propyl} triethoxysilane,
{3- [di (oxiranyl) amino] propyl} methyldimethoxysilane,
{3- [di (oxiranyl) amino] propyl} ethyldimethoxysilane,
{3- [di (oxiranyl) amino] propyl} methyldiethoxysilane,
{3- [di (oxiranyl) amino] propyl} ethyldiethoxysilane,
{3- [di (oxiranyl) amino] propyl} dimethylmethoxysilane,
{3- [di (oxiranyl) amino] propyl} diethylmethoxysilane,
{3- [di (oxiranyl) amino] propyl} dimethylethoxysilane,
Examples include {3- [di (oxiranyl) amino] propyl} diethylethoxysilane.

As the compound represented by the formula (82), as compounds in which R ⁸²⁴ and R ⁸²⁵ are tetrahydrofuranyl groups,
{3- [di (tetrahydrofuranyl) amino] propyl} trimethoxysilane,
{3- [di (tetrahydrofuranyl) amino] propyl} triethoxysilane,
{3- [di (tetrahydrofuranyl) amino] propyl} methyldimethoxysilane,
{3- [di (tetrahydrofuranyl) amino] propyl} ethyldimethoxysilane,
{3- [di (tetrahydrofuranyl) amino] propyl} methyldiethoxysilane,
{3- [di (tetrahydrofuranyl) amino] propyl} ethyldiethoxysilane,
{3- [di (tetrahydrofuranyl) amino] propyl} dimethylmethoxysilane,
{3- [di (tetrahydrofuranyl) amino] propyl} diethylmethoxysilane,
{3- [di (tetrahydrofuranyl) amino] propyl} dimethylethoxysilane,
Examples include {3- [di (tetrahydrofuranyl) amino] propyl} diethylethoxysilane.

As the compound represented by the formula (82), as compounds in which R ⁸²⁴ and R ⁸²⁵ are glycidyl groups,
{3- [di (glycidyl) amino] propyl} trimethoxysilane,
{3- [di (glycidyl) amino] propyl} triethoxysilane,
{3- [di (glycidyl) amino] propyl} methyldimethoxysilane,
{3- [di (glycidyl) amino] propyl} ethyldimethoxysilane,
{3- [di (glycidyl) amino] propyl} methyldiethoxysilane,
{3- [di (glycidyl) amino] propyl} ethyldiethoxysilane,
{3- [di (glycidyl) amino] propyl} dimethylmethoxysilane,
{3- [di (glycidyl) amino] propyl} diethylmethoxysilane,
{3- [di (glycidyl) amino] propyl} dimethylethoxysilane,
Examples include {3- [di (glycidyl) amino] propyl} diethylethoxysilane.

As the compound represented by the formula (82), as a compound in which R ⁸²⁴ and R ⁸²⁵ are tetrahydrofurfuryl groups,
{3- [di (tetrahydrofurfuryl) amino] propyl} trimethoxysilane,
{3- [di (tetrahydrofurfuryl) amino] propyl} triethoxysilane,
{3- [di (tetrahydrofurfuryl) amino] propyl} methyldimethoxysilane,
{3- [di (tetrahydrofurfuryl) amino] propyl} ethyldimethoxysilane,
{3- [di (tetrahydrofurfuryl) amino] propyl} methyldiethoxysilane,
{3- [di (tetrahydrofurfuryl) amino] propyl} ethyldiethoxysilane,
{3- [di (tetrahydrofurfuryl) amino] propyl} dimethylmethoxysilane,
{3- [di (tetrahydrofurfuryl) amino] propyl} diethylmethoxysilane,
{3- [di (tetrahydrofurfuryl) amino] propyl} dimethylethoxysilane,
Examples include {3- [di (tetrahydrofurfuryl) amino] propyl} diethylethoxysilane.

As the compound represented by the formula (82), as a compound in which R ⁸²⁴ and R ⁸²⁵ are bonded,
3- (1-piperidinyl) propyltrimethoxysilane,
3- (1-piperidinyl) propyltriethoxysilane,
3- (1-piperidinyl) propylmethyldimethoxysilane,
3- (1-piperidinyl) propylethyldimethoxysilane,
3- (1-piperidinyl) propylmethyldiethoxysilane,
3- (1-piperidinyl) propylethyldiethoxysilane,
3- (1-hexamethyleneimino) propyltrimethoxysilane,
3- (1-hexamethyleneimino) propyltriethoxysilane,
3- (1-hexamethyleneimino) propylmethyldimethoxysilane,
3- (1-hexamethyleneimino) propylethyldimethoxysilane,
3- (1-hexamethyleneimino) propylmethyldiethoxysilane,
3- (1-hexamethyleneimino) propylethyldiethoxysilane,
3-morpholinopropyltrimethoxysilane,
3-morpholinopropyltriethoxysilane,
3-morpholinopropylmethyldimethoxysilane,
3-morpholinopropylethyldimethoxysilane,
3-morpholinopropylmethyldiethoxysilane,
There may be mentioned 3-morpholinopropylethyldiethoxysilane.

As the compound represented by the formula (82), as a compound in which R ⁸²⁴ and R ⁸²⁵ are one group bonded to the nitrogen atom by a double bond,
N- (1,3-dimethylbutylidene) -3- (trimethoxysilyl) -1-propanamine,
N- (1,3-dimethylbutylidene) -3- (triethoxysilyl) -1-propanamine can be mentioned.

The compound represented by the formula (82) is preferably [3- (dialkylamino) propyl] trialkoxysilane.
More preferably,
[3- (dimethylamino) propyl] trimethoxysilane,
[3- (diethylamino) propyl] trimethoxysilane,
[3- (dimethylamino) propyl] triethoxysilane,
[3- (diethylamino) propyl] triethoxysilane,
More preferably,
[3- (Diethylamino) propyl] trimethoxysilane.

Content of the monomer unit based on the compound represented by Formula (81) is 0.01 to 20% by mass, where the total amount of the monomer units in the conjugated diene polymer is 100% by mass. The content is preferably 0.02% by mass or more, more preferably 0.05% by mass or more, in order to increase the wear resistance. Moreover, in order to improve low fuel consumption, Preferably it is 2 mass% or less, More preferably, it is 1 mass% or less, More preferably, it is 0.5 mass% or less.

The conjugated diene polymer (H) preferably has monomer units (vinyl aromatic hydrocarbon units) based on vinyl aromatic hydrocarbons in order to increase strength. Examples of the vinyl aromatic hydrocarbon include styrene, α-methylstyrene, vinyl toluene, vinyl naphthalene, divinyl benzene, trivinyl benzene, and divinyl naphthalene. Styrene is preferable.

The content of the vinyl aromatic hydrocarbon unit is 0% by mass or more (the content of the conjugated diene unit is 100% by mass or less), where the total amount of the conjugated diene unit and the vinyl aromatic hydrocarbon unit is 100% by mass. In order to increase the strength, it is preferably 10% by mass or more (the content of the conjugated diene unit is 90% by mass or less), more preferably 15% by mass or more (the content of the conjugated diene unit is 85% by mass or less). is there. In order to improve fuel economy, the content of vinyl aromatic hydrocarbon units is preferably 50% by mass or less (the content of conjugated diene units is 50% by mass or more), more preferably 45% by mass or less. (The content of the conjugated diene unit is 55% by mass or more).

The total amount of monomer units and vinyl aromatic hydrocarbon units based on the conjugated diene unit and the compound represented by the formula (81) is 100% by mass based on the total amount of monomer units in the conjugated diene polymer. In order to improve the wear resistance, the content is preferably 99.9% by mass or more, more preferably 99.95% by mass or more, and still more preferably 100% by mass.

The Mooney viscosity (ML _{1 + 4} ) of the conjugated diene polymer (H) is preferably 10 or more, more preferably 20 or more, in order to increase the strength. Moreover, in order to improve workability, Preferably it is 200 or less, More preferably, it is 150 or less. The Mooney viscosity (ML _{1 + 4} ) is measured at 100 ° C. according to JIS K6300 (1994).

The vinyl bond amount of the conjugated diene polymer (H) is preferably 80 mol% or less, more preferably 70 mol% or less, in order to improve fuel efficiency, with the content of the conjugated diene unit being 100 mol%. It is. Moreover, in order to improve grip property, Preferably it is 10 mol% or more, More preferably, it is 15 mol% or more, More preferably, it is 20 mol% or more, Most preferably, it is 40 mol% or more. The vinyl bond amount is determined from the absorption intensity in the vicinity of 910 cm ^−1, which is the absorption peak of the vinyl group, by infrared spectroscopy.

The molecular weight distribution of the conjugated diene polymer (H) is preferably 1 to 5 and more preferably 1 to 2 in order to improve fuel efficiency. The molecular weight distribution is obtained by measuring the number average molecular weight (Mn) and the weight average molecular weight (Mw) by gel permeation chromatography (GPC) method and dividing Mw by Mn.

Suitable method for producing a conjugated diene polymer (H), can be mentioned a production method having the following steps A ⁸ and B ^8.
(Step A ⁸ ): In a hydrocarbon solvent, a monomer component containing a conjugated diene and a compound represented by the above formula (81) is converted into a compound represented by the above formula (81) with an alkali metal catalyst. The amount used is 0.01 to 20% by mass (provided that the total amount of monomer components used is 100% by mass), and the monomer unit based on the conjugated diene is represented by the above formula (81). A step of obtaining a polymer having an alkali metal derived from an alkali metal catalyst at least at one end of a polymer chain having a monomer unit based on the compound to be produced.
(Step B ⁸ ): A step of reacting the polymer obtained in Step A ⁸ with the compound represented by the above formula (82).

The alkali metal catalyst used in step A ^8, may be mentioned alkali metal, organic alkali metal compound, a complex of an alkali metal and a polar compound, such as an oligomer having an alkali metal. Examples of the alkali metal include lithium, sodium, potassium, rubidium, cesium and the like. Examples of the organic alkali metal compound include ethyl lithium, n-propyl lithium, iso-propyl lithium, n-butyl lithium, sec-butyl lithium, t-octyl lithium, n-decyl lithium, phenyl lithium, 2-naphthyl lithium, 2 -Butylphenyllithium, 4-phenylbutyllithium, cyclohexyllithium, 4-cyclopentyllithium, dimethylaminopropyllithium, diethylaminopropyllithium, t-butyldimethylsiloxypropyllithium, N-morpholinopropyllithium, lithium hexamethyleneimide, lithium pyrrole Zido, lithium piperidide, lithium heptamethylene imide, lithium dodecamethylene imide, 1,4-dilithio-2-butene, sodium naphthalenide, sodium Bifenirido, such as potassium napthalenide can be mentioned. Examples of the complex of the alkali metal and the polar compound include potassium-tetrahydrofuran complex and potassium-diethoxyethane complex, and the oligomer having the alkali metal includes sodium salt of α-methylstyrene tetramer. I can give you. An organic lithium compound or an organic sodium compound is preferable, and an organic lithium compound having 2 to 20 carbon atoms or an organic sodium compound having 2 to 20 carbon atoms is more preferable.

Hydrocarbon solvents used in step A ⁸ is a solvent that does not deactivate the organic alkali metal compound catalyst may be mentioned aliphatic hydrocarbons, aromatic hydrocarbons, and alicyclic hydrocarbons. Aliphatic hydrocarbons include propane, n-butane, iso-butane, n-pentane, iso-pentane, n-hexane, propene, 1-butene, iso-butene, trans-2-butene, cis-2-butene 1-pentene, 2-pentene, 1-hexene, 2-hexene and the like. In addition, examples of the aromatic hydrocarbon include benzene, toluene, xylene, and ethylbenzene. Examples of the alicyclic hydrocarbon include cyclopentane and cyclohexane. One or more of these may be used, and the hydrocarbon solvent may be a mixture of various components such as industrial hexane. Preferably, it is a hydrocarbon having 2 to 12 carbon atoms.

In step A ^8, a hydrocarbon solvent, the alkali metal catalyst, a conjugated diene and polymerizing the monomer component containing a compound represented by the formula (81), a monomer unit derived from the conjugated diene, the A polymer having a monomer unit based on the compound represented by the formula (81) is produced. Examples of the conjugated diene include 1,3-butadiene, isoprene, 1,3-pentadiene, 2,3-dimethyl-1,3-butadiene, and 1,3-hexadiene. One or more of these are used. 1,3-butadiene and isoprene are preferred.

The amount of the compound represented by the formula (81) is preferably 0.01% by mass or more in order to increase the wear resistance when the total amount of the monomer components used in the polymerization is 100% by mass. More preferably, it is 0.02 mass% or more, More preferably, it is 0.05 mass% or more. In order to improve fuel efficiency, it is preferably 20% by mass or less, more preferably 2% by mass or less, still more preferably 1% by mass or less, and particularly preferably 0.5% by mass or less. .

In step A ^8, as a monomer, a compound represented by the conjugated diene of formula (81) may be carried out polymerization by combining vinyl aromatic hydrocarbon, the vinyl aromatic hydrocarbon include styrene, α-methylstyrene, vinyltoluene, vinylnaphthalene, divinylbenzene, trivinylbenzene, divinylnaphthalene and the like can be mentioned. Styrene is preferable.

The amount of vinyl aromatic hydrocarbon used is 0% by mass or more (the amount of conjugated diene used is 100% by mass or less), where the total amount of conjugated diene and vinyl aromatic hydrocarbon is 100% by mass. In order to increase it, it is preferably 10% by mass or more (the amount of conjugated diene used is 90% by mass or less), more preferably 15% by mass or more (the amount of conjugated diene used is 85% by mass or less). In order to improve fuel efficiency, the amount of vinyl aromatic hydrocarbon used is preferably 50% by mass or less (the amount of conjugated diene used is 50% by mass or more), more preferably 45% by mass or less (conjugated). The amount of diene used is 55% by mass or more).

In the polymerization, the total amount of the conjugated diene, the compound represented by the formula (81), and the vinyl aromatic hydrocarbon is set so that the total amount of the monomer used is 100% by mass and the wear resistance is increased. , Preferably it is 99.9 mass% or more, More preferably, it is 99.95 mass% or more, More preferably, it is 100 mass%.

Polymerization step A ⁸ is agent for adjusting the vinyl bond content of the conjugated diene unit, to adjust the distribution of the monomer unit based on a monomer other than the conjugated diene unit and a conjugated diene in the conjugated diene polymer chains in It may be carried out in the presence of an agent (hereinafter collectively referred to as “regulator”). Examples of such a regulator include ether compounds, tertiary amines, and phosphine compounds. Examples of the ether compound include cyclic ethers such as tetrahydrofuran, tetrahydropyran, and 1,4-dioxane; aliphatic monoethers such as diethyl ether and dibutyl ether; ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, and diethylene glycol diethyl ether. And aliphatic ethers such as diethylene glycol dibutyl ether; aromatic ethers such as diphenyl ether and anisole. Examples of the tertiary amine include triethylamine, tripropylamine, tributylamine, N, N, N ′, N′-tetramethylethylenediamine, N, N-diethylaniline, pyridine, quinoline and the like. Examples of the phosphine compound include trimethylphosphine, triethylphosphine, triphenylphosphine, and the like. One or more of these are used.

The polymerization temperature in step ^{A 8} is usually 25 to 100 ° C., preferably from 35 to 90 ° C.. More preferably, it is 50-80 degreeC. The polymerization time is usually 10 minutes to 5 hours.

In step B ^8, the amount of the compound represented by formula to be reacted with the polymer prepared in Step A ⁸ (82), the alkali metal per mole derived from the organic alkali metal catalyst, usually 0.1 to 3 moles Preferably, it is 0.5-2 mol, More preferably, it is 0.7-1.5 mol.

In step ^{B 8,} the temperature of reacting the compound represented by the polymer and the formula prepared in step ^{A 8} (82) is usually 25 to 100 ° C., preferably from 35 to 90 ° C.. More preferably, it is 50-80 degreeC. The reaction time is usually 60 seconds to 5 hours, preferably 5 minutes to 1 hour, more preferably 15 minutes to 1 hour.

In the production method of the conjugated diene polymer (A) to (H), if necessary, the conjugated diene polymer is added to the hydrocarbon solution of the conjugated diene polymer from the start of polymerization of the monomer using an alkali metal catalyst to the termination of polymerization. A ring agent may be added. Examples of the coupling agent include compounds represented by the following formula (X).

R _a ML _4-a (X)
(In the formula, R represents an alkyl group, an alkenyl group, a cycloalkenyl group or an aryl group, M represents a silicon atom or a tin atom, L represents a halogen atom or a hydrocarbyloxy group, and a represents an integer of 0 to 2. Represents.)

As the coupling agent represented by the formula (X), silicon tetrachloride, methyltrichlorosilane, dimethyldichlorosilane, trimethylchlorosilane, tin tetrachloride, methyltrichlorotin, dimethyldichlorotin, trimethylchlorotin, tetramethoxysilane, methyl Examples include trimethoxysilane, dimethoxydimethylsilane, methyltriethoxysilane, ethyltrimethoxysilane, dimethoxydiethylsilane, diethoxydimethylsilane, tetraethoxysilane, ethyltriethoxysilane, and diethoxydiethylsilane.

The addition amount of the coupling agent is preferably 0.03 mol or more, more preferably 0.05 mol or more, per 1 mol of alkali metal derived from the alkali metal catalyst in order to improve the processability of the conjugated diene polymer. It is. Moreover, in order to improve low-fuel-consumption property, Preferably it is 0.4 mol or less, More preferably, it is 0.3 mol or less.

Conjugated diene polymers (A) to (H) can be obtained by a known recovery method, for example, (1) a method of adding a coagulant to a hydrocarbon solution of a conjugated diene polymer, or (2) a conjugated diene polymer. It can be recovered from the hydrocarbon solution of the conjugated diene polymer by the method of adding steam to the hydrocarbon solution. The recovered conjugated diene polymer may be dried by a known dryer such as a band dryer or an extrusion dryer.

Conjugated diene polymers (A) to (H) can be used as rubber components, and other rubber components and additives such as silica can be blended to obtain the rubber composition of the present invention. .

The content of the conjugated diene polymers (A) to (H) in 100% by mass of the rubber component is 5% by mass or more, preferably 20% by mass or more, more preferably 40% by mass or more. If the amount is less than 5% by mass, the effect of improving fuel economy tends to be difficult to obtain. Further, the content of the conjugated diene polymer is preferably 90% by mass or less, more preferably 80% by mass or less. When it exceeds 90% by mass, the wear resistance is lowered and the cost tends to be high.

The rubber component that can be used in addition to the conjugated diene polymers (A) to (H) is not limited. For example, natural rubber (NR), isoprene rubber (IR), butadiene rubber (BR), and styrene butadiene rubber (SBR). , Acrylonitrile butadiene rubber (NBR), chloroprene rubber (CR), butyl rubber (IIR) and the like. These rubber components may be used alone or in combination of two or more. Of these, NR and BR are preferred because they exhibit a good balance between low fuel consumption, wet grip performance and wear resistance.
These rubber components are not particularly limited, and those generally used in the tire industry can be used.

The content of NR in 100% by mass of the rubber component is preferably 5% by mass or more, more preferably 15% by mass or more. If the amount is less than 5% by mass, sufficient fuel economy tends not to be obtained. The NR content is preferably 60% by mass or less, more preferably 40% by mass or less. When it exceeds 60 mass%, workability tends to deteriorate.

The content of BR in 100% by mass of the rubber component is preferably 5% by mass or more, more preferably 15% by mass or more. When it is less than 5% by mass, sufficient wear resistance tends to be not obtained. Further, the BR content is preferably 60% by mass or less, more preferably 40% by mass or less. When it exceeds 60% by mass, fuel efficiency tends to deteriorate.

The rubber composition of the present invention contains conductive carbon black. By blending the conductive carbon black together with the conjugated diene polymers (A) to (H) and silica, the fuel economy, wet grip performance and wear resistance can be improved in a well-balanced manner.

The nitrogen adsorption specific surface area (N ₂ SA) of the conductive carbon black is preferably 40 m ² / g or more, more preferably 60 m ² / g or more, and further preferably 65 m ² / g or more. If it is less than 40 m < ² > / g, there exists a tendency for favorable electroconductivity not to be obtained. Also, _N 2 SA of the conductive carbon black is preferably ^{80 m} 2 / g or less, and more preferably not more than ^70m 2 / g. When it exceeds 80 m ² / g, there is a tendency that sufficient dispersion cannot be obtained and good performance cannot be exhibited.
Incidentally, _N 2 SA of the conductive carbon black is a value measured in accordance with ASTM D4820-93.

Dibutyl phthalate oil absorption of the conductive carbon black (DBP oil absorption) is preferably 110 cm ^3/100 g or more, more preferably 150 ml / 100 g or more, further preferably 170 ml / 100 g or more. 110 cm ³ is less than / 100 g, it tends not sufficient conductivity can be obtained. Further, DBP oil absorption of the conductive carbon black is preferably 230 cm ^3/100 g or less, and more preferably not more than 220 cm ^3/100 g. Exceeds 230 cm ^3/100 _g, similar to the _N 2 SA, there is a tendency that the dispersion is not obtained sufficient carbon black.
The DBP oil absorption of conductive carbon black is a value measured according to ASTM D2414-93.

Conductive carbon black has a colloidal property, and its particle density is lower than that of general-purpose carbon black. Therefore, it has a three-dimensionally connected network structure compared to the case where the same mass part of general-purpose carbon black is added. It is considered that an improvement effect such as wear resistance appears.

Specific examples of the conductive carbon black include those exhibiting excellent conductivity such as acetylene black, ketjen black, and graphitized carbon black, and acetylene black can be suitably used. These may be used alone or in combination of two or more.

Content of electroconductive carbon black is 3 mass parts or more with respect to 100 weight part of rubber components, and it is preferable that it is 10 mass parts or more. When the amount is less than 3 parts by mass, there is a tendency that an improvement effect such as wear resistance is not observed. This is considered because the effect of conductive carbon black is diluted. Moreover, content of electroconductive carbon black is 30 mass parts or less, and it is preferable that it is 20 mass parts or less. When it exceeds 30 parts by mass, the wear resistance tends to deteriorate. This is presumably because the elongation of the rubber composition decreases due to excessive formation of the conductive carbon black structure.

In the production of the rubber composition, the introduction of conductive carbon black is confirmed to be effective at any stage of kneading, re-kneading, and finishing kneading, but it needs to be appropriately distributed in the rubber matrix. It is preferable to be introduced in the first half of the kneading process as much as possible.

In addition, when blended with oil, wax, a resin whose melting point melts with the heat history during the kneading process, and a low molecular component that flows, a master batch process for premixing the rubber component and conductive carbon black is performed. It is preferable to provide it. This is because the above components easily penetrate into the voids inside the aggregate due to the low particle density of the conductive carbon black, improving the dispersion and distribution of the conductive carbon black in the rubber component and the wear resistance. This is considered to be because the wettability and the degree of interaction with the polymer necessary for the decrease.

Furthermore, in order to promote the penetration of the polymer into the fine internal voids of the conductive carbon black, after the temperature rise due to mastication, it is better to cool again as much as possible at a temperature higher than the temperature at which the rubber becomes brittle, and then kneaded again. . As a result, the polymer penetrates into the inside of the conductive carbon black, and the power of the mixer is transmitted through the wet polymer, thereby promoting the dispersion by applying the largest shear stress to the aggregate of the conductive carbon black. In addition, since the polymer wets and spreads on the surface of the conductive carbon black without any gap, the interaction at the interface between the conductive carbon black and the polymer becomes the strongest, and the reinforcement can be maximized.

The rubber composition of the present invention contains silica. By blending silica together with the conjugated diene polymers (A) to (H) and conductive carbon black, fuel economy, wet grip performance and wear resistance can be improved in a well-balanced manner. The silica is not particularly limited, and for example, those commonly used in the tire industry such as dry method silica (anhydrous silica) and wet method silica (hydrous silica) can be used. Silica may be used alone or in combination of two or more.

The BET specific surface area of silica is preferably 50 to 250 m ² / g. The BET specific surface area is measured according to ASTM D1993-03. As a commercial product of silica, the product name Ultrasil VN3-G manufactured by Degussa, the product name VN3, AQ, ER, RS-150 manufactured by Tosoh Silica Co., Ltd., and the product names Zeosil 1115MP, 1165MP manufactured by Rhodia can be used. .

The content of silica is 5 to 150 parts by mass with respect to 100 parts by mass of the rubber component. The content is preferably 30 parts by mass or more, more preferably 50 parts by mass or more, in order to improve fuel efficiency. Moreover, in order to improve abrasion resistance and intensity | strength, Preferably it is 120 mass parts or less, More preferably, it is 100 mass parts or less.

The rubber composition of the present invention may contain additives other than the above-mentioned chemicals. Known additives can be used, such as sulfur vulcanizing agents; thiazole vulcanization accelerators, thiuram vulcanization accelerators, sulfenamide vulcanization accelerators, guanidine vulcanization accelerators. Vulcanization accelerators such as stearic acid and zinc oxide; organic peroxides such as dicumyl peroxide and ditertiary butyl peroxide; reinforcing agents; calcium carbonate, talc, alumina, clay, water Examples include fillers such as aluminum oxide and mica; silane coupling agents; extension oils; processing aids; anti-aging agents;

Examples of the sulfur include powdered sulfur, precipitated sulfur, colloidal sulfur, insoluble sulfur, and highly dispersible sulfur. The sulfur content is preferably 0.1 parts by mass or more, more preferably 0.3 parts by mass or more, still more preferably 0.5 parts by mass or more, and preferably 100 parts by mass or more, more preferably 0.5 parts by mass or more. 15 parts by mass or less, more preferably 10 parts by mass or less, and still more preferably 5 parts by mass or less.

Examples of the vulcanization accelerator include 2-mercaptobenzothiazole, dibenzothiazyl disulfide, and thiazole vulcanization accelerators such as N-cyclohexyl-2-benzothiazylsulfenamide; tetramethylthiuram monosulfide, tetramethylthiuram. Thiuram vulcanization accelerators such as disulfides; N-cyclohexyl-2-benzothiazole sulfenamide, Nt-butyl-2-benzothiazole sulfenamide, N-oxyethylene-2-benzothiazole sulfenamide, N -Sulfenamide vulcanization accelerators such as oxyethylene-2-benzothiazole sulfenamide and N, N'-diisopropyl-2-benzothiazole sulfenamide; diphenylguanidine, diortolylguanidine, orthotolylbiguanidine What guanidine-based vulcanization accelerator and the like. The content of the vulcanization accelerator is preferably 0.1 to 5 parts by mass, more preferably 0.2 to 3 parts by mass with respect to 100 parts by mass of the rubber component.

A general general-purpose carbon black can be used as the reinforcing agent, and examples of the general-purpose carbon black include SAF, ISAF, HAF, MAF, FEF, SRF, GPF, APF, FF, CF, SCF, and ECF. Furnace black such as; acetylene black; thermal black such as FT and MT; channel black such as EPC, MPC and CC; graphite and the like. One or more of these can be used.

The nitrogen adsorption specific surface area (N ₂ SA) of general-purpose carbon black is usually 5 to 200 m ² / g, preferably 75 to ²⁰⁰ m ² / g, and more preferably 85 to ²⁰⁰ m ² / g. Further, general-purpose carbon black dibutyl phthalate (DBP) absorption is usually 5~300cm ³ / 100g. The nitrogen adsorption specific surface area is measured according to ASTM D4820-93, and the DBP absorption is measured according to ASTM D2414-93.

The content of the reinforcing agent is preferably 10 to 150 parts by mass with respect to 100 parts by mass of the rubber component. Further, the content is more preferably 20 parts by mass or more, and still more preferably 30 parts by mass or more, in order to increase wear resistance and strength. Moreover, in order to improve low fuel consumption, More preferably, it is 120 mass parts or less, More preferably, it is 100 mass parts or less.

Moreover, as mass ratio (content of a silica: content of conductive carbon black) of content of the silica used as a reinforcing agent, and content of conductive carbon black, it is 1: 1-50: 1. preferable. The mass ratio is more preferably 5: 1 to 20: 1 in order to increase fuel efficiency and enhance reinforcement.

Examples of the silane coupling agent include vinyltrichlorosilane, vinyltriethoxysilane, vinyltris (β-methoxyethoxy) silane, β- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, and γ-glycidoxypropyltrimethoxysilane. , Γ-methacryloxypropyltrimethoxysilane, N- (β-aminoethyl) -γ-aminopropyltrimethoxysilane, N- (β-aminoethyl) -γ-aminopropylmethyldimethoxysilane, N-phenyl-γ- Aminopropyltrimethoxysilane, γ-chloropropyltrimethoxysilane, γ-mercaptopropyltrimethoxysilane, γ-aminopropyltriethoxysilane, bis (3- (triethoxysilyl) propyl) disulfide, bis (3- (triethoxy Cyril) Pills) tetrasulfide, .gamma.-trimethoxysilylpropyl dimethylthiocarbamoyl tetrasulfide, and the like .gamma.-trimethoxysilylpropyl benzothiazyl tetrasulfide. One or more of these are used. As commercial products, trade names Si69, Si75, etc., manufactured by Degussa Corporation can be used.

The content of the silane coupling agent is preferably 1 to 20 parts by mass, more preferably 2 to 15 parts by mass, and further preferably 5 to 10 parts by mass with respect to 100 parts by mass of silica.

Examples of the extending oil include aromatic mineral oil (viscosity specific gravity constant (VGC value) 0.900 to 1.049), naphthenic mineral oil (VGC value 0.850 to 0.899), paraffinic mineral oil (VGC value 0.790 to 0.849), and the like. The polycyclic aromatic content of the extender oil is preferably less than 3% by mass, more preferably less than 1% by mass. The polycyclic aromatic content is measured according to the British Petroleum Institute 346/92 method. Moreover, the aromatic compound content (CA) of the extending oil is preferably 20% by mass or more. One or more of these extending oils are used.

As a method for producing the rubber composition of the present invention, a known method, for example, a method of kneading each component with a known mixer such as a roll or Banbury can be used.

As kneading conditions, when additives other than the vulcanizing agent and the vulcanization accelerator are blended, the kneading temperature is usually 50 to 200 ° C., preferably 80 to 190 ° C., and the kneading time is usually 30 seconds. -30 minutes, preferably 1-30 minutes. When blending a vulcanizing agent and a vulcanization accelerator, the kneading temperature is usually 100 ° C. or lower, preferably room temperature to 80 ° C. A composition containing a vulcanizing agent and a vulcanization accelerator is usually used after vulcanization treatment such as press vulcanization. The vulcanization temperature is usually 120 to 200 ° C, preferably 140 to 180 ° C.

The rubber composition of the present invention has a high level of good balance between low fuel consumption, wet grip performance and wear resistance.

The rubber composition of the present invention is used for tire treads (cap treads).

The pneumatic tire of the present invention is produced by a usual method using the rubber composition. That is, a rubber composition containing various additives as necessary is extruded in accordance with the shape of the tread of the tire at an unvulcanized stage, molded by a normal method on a tire molding machine, etc. The tire members are bonded together to form an unvulcanized tire. This unvulcanized tire can be heated and pressurized in a vulcanizer to produce the pneumatic tire of the present invention.

The pneumatic tire of the present invention can be suitably used as a tire for passenger cars.

The present invention will be specifically described based on examples, but the present invention is not limited to these examples.

(Polymer production example 1)
The inside of the stainless steel polymerization reactor with an internal volume of 5 liters equipped with a stirrer was washed, dried and replaced with dry nitrogen. Next, 2.55 kg of industrial hexane (density 680 kg / m ³ ), 137 g of 1,3-butadiene, 43 g of styrene, a mixture of 3- (1-pyrrolidinyl) ethylstyrene and 4- (1-pyrrolidinyl) ethylstyrene. 53 g, 1.52 ml of tetrahydrofuran, and 1.18 ml of ethylene glycol diethyl ether were charged into the polymerization reactor. Next, 0.64 g of bis (diethylamino) methylvinylsilane and an n-hexane solution of n-butyllithium (content of n-butyllithium 3.98 mmol) were charged into the polymerization reactor to initiate the polymerization reaction. .

1,3-butadiene, styrene, bis (diethylamino) methylvinylsilane while stirring rate is 130 rpm, polymerization reactor temperature is 65 ° C., and 1,3-butadiene and styrene are continuously fed into the polymerization reactor. Copolymerization reaction of 3- (1-pyrrolidinyl) ethylstyrene and 4- (1-pyrrolidinyl) ethylstyrene was performed for 2 hours. The supply amount of 1,3-butadiene was 205 g, and the supply amount of styrene was 65 g. Of the total amount of monomers charged / supplied to the polymerization reactor, the amount of the mixture of 3- (1-pyrrolidinyl) ethylstyrene and 4- (1-pyrrolidinyl) ethylstyrene was 0.12% by mass, bis (diethylamino) methyl The amount of vinylsilane charged was 0.14% by mass.

10 ml of hexane solution containing 0.5 ml of methanol was added to the polymer solution, and the polymer solution was stirred for 5 minutes. Next, 2-tert-butyl-6- (3-tert-butyl-2-hydroxy-5-methylbenzyl) -4-methylphenyl acrylate (manufactured by Sumitomo Chemical Co., Ltd., trade name: Sumilizer GM) was added to the polymer solution. ) 1.8 g, pentaerythrityltetrakis (3-laurylthiopropionate) (Sumitomo Chemical Co., Ltd., trade name: Sumilizer TP-D) 0.9 g was added, and then the polymer solution was cooled to room temperature. Evaporation was performed in 24 hours, and the resultant was further dried under reduced pressure at 55 ° C. for 12 hours to obtain a polymer 1.

(Polymer production example 2)
The inside of the stainless steel polymerization reactor with an internal volume of 5 liters equipped with a stirrer was washed, dried and replaced with dry nitrogen. Next, 2.55 kg of industrial hexane (density 680 kg / m ³ ), 137 g of 1,3-butadiene, 43 g of styrene, a mixture of 3- (1-pyrrolidinyl) ethylstyrene and 4- (1-pyrrolidinyl) ethylstyrene 81 g, 1.52 ml of tetrahydrofuran and 1.18 ml of ethylene glycol diethyl ether were charged into the polymerization reactor. Next, 3.81 mmol of n-butyllithium was charged into the polymerization reactor as an n-hexane solution to initiate the polymerization reaction.

The stirring speed was 130 rpm, the temperature in the polymerization reactor was 65 ° C., and 1,3-butadiene and styrene, 3- (1-pyrrolidinyl) were continuously fed into the polymerization reactor. ) Ethylene styrene and 4- (1-pyrrolidinyl) ethyl styrene were copolymerized for 2 hours. The supply amount of 1,3-butadiene was 205 g, and the supply amount of styrene was 65 g. In the total amount of monomers charged / supplied to the polymerization reactor, the charged amount of the mixture of 3- (1-pyrrolidinyl) ethylstyrene and 4- (1-pyrrolidinyl) ethylstyrene was 0.40% by mass.

10 ml of hexane solution containing 0.5 ml of methanol was added to the polymer solution, and the polymer solution was stirred for 5 minutes. Next, 2-tert-butyl-6- (3-tert-butyl-2-hydroxy-5-methylbenzyl) -4-methylphenyl acrylate (manufactured by Sumitomo Chemical Co., Ltd., trade name: Sumilizer GM) was added to the polymer solution. ) 1.8 g, pentaerythrityltetrakis (3-laurylthiopropionate) (Sumitomo Chemical Co., Ltd., trade name: Sumilizer TP-D) 0.9 g was added, and then the polymer solution was cooled to room temperature. Evaporation was performed in 24 hours, and the resultant was further dried under reduced pressure at 55 ° C. for 12 hours to obtain a polymer 2.

(Polymer production example 3)
The inside of the stainless steel polymerization reactor with an internal volume of 5 liters equipped with a stirrer was washed, dried and replaced with dry nitrogen. Next, 2.55 kg of industrial hexane (density 680 kg / m ³ ), 137 g of 1,3-butadiene, 43 g of styrene, a mixture of 3- (1-pyrrolidinyl) ethylstyrene and 4- (1-pyrrolidinyl) ethylstyrene. 53 g, 1.52 ml of tetrahydrofuran, and 1.18 ml of ethylene glycol diethyl ether were charged into the polymerization reactor. Next, 3.73 mmol of n-butyllithium was charged into the polymerization reactor as an n-hexane solution to initiate the polymerization reaction.

The stirring speed was 130 rpm, the temperature in the polymerization reactor was 65 ° C., and 1,3-butadiene and styrene, 3- (1-pyrrolidinyl) were continuously fed into the polymerization reactor. ) Copolymerization reaction of ethylstyrene and 4- (1-pyrrolidinyl) ethylstyrene was carried out for 2 hours. The supply amount of 1,3-butadiene was 205 g, and the supply amount of styrene was 65 g. In the total amount of monomers charged and supplied to the polymerization reactor, the charged amount of the mixture of 3- (1-pyrrolidinyl) ethylstyrene and 4- (1-pyrrolidinyl) ethylstyrene was 0.12% by mass.

10 ml of hexane solution containing 0.5 ml of methanol was added to the polymer solution, and the polymer solution was stirred for 5 minutes. Next, 2-tert-butyl-6- (3-tert-butyl-2-hydroxy-5-methylbenzyl) -4-methylphenyl acrylate (manufactured by Sumitomo Chemical Co., Ltd., trade name: Sumilizer GM) was added to the polymer solution. ) 1.8 g, pentaerythrityltetrakis (3-laurylthiopropionate) (Sumitomo Chemical Co., Ltd., trade name: Sumilizer TP-D) 0.9 g was added, and then the polymer solution was cooled to room temperature. Evaporation was performed in 24 hours, and the resultant was further dried under reduced pressure at 55 ° C. for 12 hours to obtain a polymer 3.

(Polymer production example 4)
The inside of the stainless steel polymerization reactor with an internal volume of 20 liters equipped with a stirrer was washed, dried, and replaced with dry nitrogen. Next, 10.2 kg of industrial hexane (density 680 kg / m ³ ), 608 g of 1,3-butadiene, 192 g of styrene, 6.1 ml of tetrahydrofuran, and 4.0 ml of ethylene glycol diethyl ether were charged into the polymerization reactor. Next, 5.43 g of bis (diethylamino) methylvinylsilane and n-hexane solution of n-butyllithium (content of n-butyllithium 14.72 mmol) were charged into the polymerization reactor to initiate the polymerization reaction. .

1,3-butadiene, styrene, bis (diethylamino) methylvinylsilane while stirring rate is 130 rpm, polymerization reactor temperature is 65 ° C., and 1,3-butadiene and styrene are continuously fed into the polymerization reactor. The copolymerization reaction of was carried out for 3 hours. The amount of 1,3-butadiene supplied was 912 g, and the amount of styrene supplied was 288 g. In the total amount of monomers charged / supplied to the polymerization reactor, the charged amount of bis (diethylamino) methylvinylsilane was 0.27% by mass.

20 ml of hexane solution containing 0.8 ml of methanol was added to the polymer solution, and the polymer solution was stirred for 5 minutes. Next, 2-tert-butyl-6- (3-tert-butyl-2-hydroxy-5-methylbenzyl) -4-methylphenyl acrylate (manufactured by Sumitomo Chemical Co., Ltd., trade name: Sumilizer GM) was added to the polymer solution. ) 8.0 g, pentaerythrityltetrakis (3-laurylthiopropionate) (Sumitomo Chemical Co., Ltd., trade name: Sumilizer TP-D) 4.0 g was added, and then the polymer solution was cooled to room temperature. Evaporation was performed in 24 hours, and the resultant was further dried under reduced pressure at 55 ° C. for 12 hours to obtain a polymer 4.

(Polymer Production Example 5)
The inside of the stainless steel polymerization reactor with an internal volume of 5 liters equipped with a stirrer was washed, dried and replaced with dry nitrogen. Next, industrial hexane (density 680 kg / m ³ ) 2.55 kg, 1,3-butadiene 137 g, styrene 43 g, 4-N, N-dimethylaminomethylstyrene 0.43 g, tetrahydrofuran 1.52 ml, ethylene glycol diethyl ether 1.18 ml was charged into the polymerization reactor. Next, 0.64 g of bis (diethylamino) methylvinylsilane and an n-hexane solution of n-butyllithium (content of n-butyllithium 3.59 mmol) were charged into the polymerization reactor to initiate the polymerization reaction. .

1,3-butadiene, styrene, bis (diethylamino) methylvinylsilane while stirring rate is 130 rpm, polymerization reactor temperature is 65 ° C., and 1,3-butadiene and styrene are continuously fed into the polymerization reactor. And 4-N, N-dimethylaminomethylstyrene was copolymerized for 2 hours. The supply amount of 1,3-butadiene was 205 g, and the supply amount of styrene was 65 g. Of the total amount of monomers charged / supplied to the polymerization reactor, the amount of 4-N, N-dimethylaminomethylstyrene charged was 0.10% by mass, and the amount of bis (diethylamino) methylvinylsilane charged was 0.14% by mass. there were.

10 ml of hexane solution containing 0.5 ml of methanol was added to the polymer solution, and the polymer solution was stirred for 5 minutes. Next, 2-tert-butyl-6- (3-tert-butyl-2-hydroxy-5-methylbenzyl) -4-methylphenyl acrylate (manufactured by Sumitomo Chemical Co., Ltd., trade name: Sumilizer GM) was added to the polymer solution. ) 1.8 g, pentaerythrityltetrakis (3-laurylthiopropionate) (Sumitomo Chemical Co., Ltd., trade name: Sumilizer TP-D) 0.9 g was added, and then the polymer solution was cooled to room temperature. Evaporation was performed in 24 hours, and the resultant was further dried under reduced pressure at 55 ° C. for 12 hours to obtain a polymer 5.

(Polymer Production Example 6)
The inside of the stainless steel polymerization reactor with an internal volume of 20 liters equipped with a stirrer was washed, dried, and replaced with dry nitrogen. Next, 10.2 kg of industrial hexane (density 680 kg / m ³ ), 608 g of 1,3-butadiene, 192 g of styrene, 2.04 g of 4-N, N-dimethylaminomethylstyrene, 6.1 ml of tetrahydrofuran, ethylene glycol diethyl ether 4.0 ml was charged into the polymerization reactor. Next, 15.89 mmol of n-butyllithium was charged into the polymerization reactor as an n-hexane solution to start the polymerization reaction.

While stirring speed is 130 rpm, polymerization reactor internal temperature is 65 ° C., and 1,3-butadiene and styrene are continuously fed into the polymerization reactor, 1,3-butadiene, styrene, and 4-N, The copolymerization reaction of N-dimethylaminomethylstyrene was performed for 3 hours. The amount of 1,3-butadiene supplied was 912 g, and the amount of styrene supplied was 288 g. In the total amount of monomers charged / supplied to the polymerization reactor, the amount of 4-N, N-dimethylaminomethylstyrene charged was 0.10% by mass.

20 ml of hexane solution containing 0.8 ml of methanol was added to the polymer solution, and the polymer solution was stirred for 5 minutes. Next, 2-tert-butyl-6- (3-tert-butyl-2-hydroxy-5-methylbenzyl) -4-methylphenyl acrylate (manufactured by Sumitomo Chemical Co., Ltd., trade name: Sumilizer GM) was added to the polymer solution. ) 8.0 g, pentaerythrityltetrakis (3-laurylthiopropionate) (Sumitomo Chemical Co., Ltd., trade name: Sumilizer TP-D) 4.0 g was added, and then the polymer solution was cooled to room temperature. Evaporation was performed in 24 hours, and the resultant was further dried under reduced pressure at 55 ° C. for 12 hours to obtain a polymer 6.

(Polymer Production Example 7)
The inside of the stainless steel polymerization reactor with an internal volume of 5 liters equipped with a stirrer was washed, dried and replaced with dry nitrogen. Next, industrial hexane (density 680 kg / m ³ ) 2.55 kg, 1,3-butadiene 137 g, styrene 43 g, 4-N, N-bis (trimethylsilyl) aminostyrene 0.70 g, tetrahydrofuran 1.52 ml, ethylene glycol 1.18 ml of diethyl ether was charged into the polymerization reactor. Next, 0.64 g of bis (diethylamino) methylvinylsilane and an n-hexane solution of n-butyllithium (content of n-butyllithium 3.66 mmol) were charged into the polymerization reactor to initiate the polymerization reaction. .

1,3-butadiene, styrene, bis (diethylamino) methylvinylsilane while stirring rate is 130 rpm, polymerization reactor temperature is 65 ° C., and 1,3-butadiene and styrene are continuously fed into the polymerization reactor. And 4-N, N-bis (trimethylsilyl) aminostyrene was copolymerized for 2 hours. The supply amount of 1,3-butadiene was 205 g, and the supply amount of styrene was 65 g. Of the total amount of monomers charged / supplied to the polymerization reactor, the amount of 4-N, N-bis (trimethylsilyl) aminostyrene charged was 0.16% by mass, and the amount of bis (diethylamino) methylvinylsilane charged was 0.14%. %Met.

10 ml of hexane solution containing 0.5 ml of methanol was added to the polymer solution, and the polymer solution was stirred for 5 minutes. Next, 2-tert-butyl-6- (3-tert-butyl-2-hydroxy-5-methylbenzyl) -4-methylphenyl acrylate (manufactured by Sumitomo Chemical Co., Ltd., trade name: Sumilizer GM) was added to the polymer solution. ) 1.8 g, pentaerythrityltetrakis (3-laurylthiopropionate) (Sumitomo Chemical Co., Ltd., trade name: Sumilizer TP-D) 0.9 g was added, and then the polymer solution was cooled to room temperature. Evaporation was performed in 24 hours, and the resultant was further dried under reduced pressure at 55 ° C. for 12 hours to obtain a polymer 7.

(Polymer Production Example 8)
The inside of the stainless steel polymerization reactor with an internal volume of 5 liters equipped with a stirrer was washed, dried and replaced with dry nitrogen. Next, industrial hexane (density 680 kg / m ³ ) 2.55 kg, 1,3-butadiene 137 g, styrene 43 g, tetrahydrofuran 1.52 ml, ethylene glycol diethyl ether 1.18 ml, 4-N, N-bis (trimethylsilyl) Aminostyrene 0.70 g was charged into the polymerization reactor. Next, 3.81 mmol of n-butyllithium was charged into the polymerization reactor as an n-hexane solution to initiate the polymerization reaction.

While stirring speed is 130 rpm, polymerization reactor internal temperature is 65 ° C., and 1,3-butadiene and styrene are continuously fed into the polymerization reactor, 1,3-butadiene, styrene, and 4-N, The copolymerization reaction of N-bis (trimethylsilyl) aminostyrene was performed for 2 hours. The supply amount of 1,3-butadiene was 205 g, and the supply amount of styrene was 65 g. The total amount of 4-N, N-bis (trimethylsilyl) aminostyrene charged in the total amount of monomers charged and supplied to the polymerization reactor was 0.16% by mass.

10 ml of hexane solution containing 0.5 ml of methanol was added to the polymer solution, and the polymer solution was stirred for 5 minutes. Next, 2-tert-butyl-6- (3-tert-butyl-2-hydroxy-5-methylbenzyl) -4-methylphenyl acrylate (manufactured by Sumitomo Chemical Co., Ltd., trade name: Sumilizer GM) was added to the polymer solution. ) 1.8 g, pentaerythrityltetrakis (3-laurylthiopropionate) (Sumitomo Chemical Co., Ltd., trade name: Sumilizer TP-D) 0.9 g was added, and then the polymer solution was cooled to room temperature. Evaporation was performed in 24 hours, and the resultant was further dried under reduced pressure at 55 ° C. for 12 hours to obtain a polymer 8.

(Polymer production example 9)
A stainless polymerization reactor with an internal volume of 20 liters equipped with a stirrer was washed, dried and replaced with dry nitrogen. Next, 10.2 kg of industrial hexane (density 680 kg / m ³ ), 608 g of 1,3-butadiene, 192 g of styrene, a mixture of 3- (1-pyrrolidinyl) ethylstyrene and 4- (1-pyrrolidinyl) ethylstyrene 58 g, 6.1 ml of tetrahydrofuran, and 4.1 ml of ethylene glycol diethyl ether were charged into the polymerization reactor. Next, 2.74 g of bis (diethylamino) methylvinylsilane and n-hexane solution of n-butyllithium (n-butyllithium content 15.04 mmol) were charged into the polymerization reactor to initiate the polymerization reaction.
The stirring speed was 130 rpm, the temperature in the polymerization reactor was 65 ° C., and 1,3-butadiene and styrene, 3- (1-pyrrolidinyl) were continuously fed into the polymerization reactor. ) Ethylstyrene, 4- (1-pyrrolidinyl) ethylstyrene, and bis (diethylamino) methylvinylsilane were copolymerized for 3 hours. The amount of 1,3-butadiene supplied was 912 g, and the amount of styrene supplied was 288 g. In the total amount of monomers charged / supplied to the polymerization reactor, the amount of the mixture of 3- (1-pyrrolidinyl) ethylstyrene and 4- (1-pyrrolidinyl) ethylstyrene was 0.13% by mass, and bis (diethylamino ) The amount of methylvinylsilane charged was 0.14% by mass.
Next, the obtained polymerization reaction solution was stirred at a stirring speed of 130 rpm, 12.8 mmol of [3- (diethylamino) propyl] trimethoxysilane was added to the polymer solution, and further stirred for 15 minutes. Next, 20 ml of hexane solution containing 0.8 ml of methanol was added to the polymer solution, and the polymer solution was further stirred for 5 minutes.
7. 2-tert-butyl-6- (3-tert-butyl-2-hydroxy-5-methylbenzyl) -4-methylphenyl acrylate (manufactured by Sumitomo Chemical Co., Ltd., trade name: Sumilyzer GM) in the polymer solution 0 g, pentaerythrityltetrakis (3-laurylthiopropionate) (Sumitomo Chemical Co., Ltd., trade name: Sumilyzer TP-D) 4.0 g was added, and then the polymer solution was added at room temperature for 24 hours. Evaporated and further dried under reduced pressure at 55 ° C. for 12 hours to obtain a polymer 9.

(Polymer production example 10)
A stainless polymerization reactor with an internal volume of 20 liters equipped with a stirrer was washed, dried and replaced with dry nitrogen. Next, 10.2 kg of industrial hexane (density 680 kg / m ³ ), 547 g of 1,3-butadiene, 173 g of styrene, 6.1 ml of tetrahydrofuran, and 4.7 ml of ethylene glycol diethyl ether were charged into the polymerization reactor. Next, 15.38 mmol of n-butyllithium was charged into the polymerization reactor as an n-hexane solution to initiate the polymerization reaction.
The stirring reaction rate is 130 rpm, the temperature in the polymerization reactor is 65 ° C., and the copolymerization reaction of 1,3-butadiene and styrene is performed for 3 hours while continuously supplying 1,3-butadiene and styrene into the polymerization reactor. went. The amount of 1,3-butadiene supplied was 821 g, and the amount of styrene supplied was 259 g.
Next, the obtained polymerization reaction solution was stirred at a stirring speed of 130 rpm, and 12.80 mmol of [3- (diethylamino) propyl] trimethoxysilane was added to the polymer solution, and further stirred for 15 minutes. Next, 20 ml of hexane solution containing 0.8 ml of methanol was added to the polymer solution, and the polymer solution was further stirred for 5 minutes.
7. 2-tert-butyl-6- (3-tert-butyl-2-hydroxy-5-methylbenzyl) -4-methylphenyl acrylate (manufactured by Sumitomo Chemical Co., Ltd., trade name: Sumilyzer GM) in the polymer solution 0 g, pentaerythrityltetrakis (3-laurylthiopropionate) (Sumitomo Chemical Co., Ltd., trade name: Sumilyzer TP-D) 4.0 g was added, and then the polymer solution was added at room temperature for 24 hours. Evaporated and further dried under reduced pressure at 55 ° C. for 12 hours to obtain a polymer 10.

(Polymer Production Example 11)
A stainless polymerization reactor with an internal volume of 20 liters equipped with a stirrer was washed, dried and replaced with dry nitrogen. Next, 10.2 kg of industrial hexane (density 680 kg / m ³ ), 608 g of 1,3-butadiene, 192 g of styrene, 6.1 ml of tetrahydrofuran, and 4.4 ml of ethylene glycol diethyl ether were charged into the polymerization reactor. Next, 2.63 g of bis (diethylamino) methylvinylsilane and an n-hexane solution of n-butyllithium (n-butyllithium content 14.68 mmol) were charged into the polymerization reactor to initiate the polymerization reaction.
While stirring speed is 130 rpm, polymerization reactor internal temperature is 65 ° C. and 1,3-butadiene and styrene are continuously fed into the polymerization reactor, 1,3-butadiene, styrene and bis (diethylamino) The copolymerization reaction of methyl vinyl silane was performed for 3 hours. The amount of 1,3-butadiene supplied was 912 g, and the amount of styrene supplied was 288 g. In the total amount of monomers charged / supplied to the polymerization reactor, the charged amount of bis (diethylamino) methylvinylsilane was 0.13% by mass.
20 ml of hexane solution containing 0.8 ml of methanol was added to the polymer solution, and the polymer solution was stirred for 5 minutes. Next, 2-tert-butyl-6- (3-tert-butyl-2-hydroxy-5-methylbenzyl) -4-methylphenyl acrylate (manufactured by Sumitomo Chemical Co., Ltd., trade name: Sumilizer GM) was added to the polymer solution. ) 8.0 g, pentaerythrityltetrakis (3-laurylthiopropionate) (Sumitomo Chemical Co., Ltd., trade name: Sumilizer TP-D) 4.0 g was added, and then the polymer solution was cooled to room temperature. Evaporation was performed in 24 hours, and the resultant was further dried under reduced pressure at 55 ° C. for 12 hours to obtain a polymer 11.

(Polymer Production Example 12)
A stainless polymerization reactor with an internal volume of 5 liters equipped with a stirrer was washed, dried and replaced with dry nitrogen. Next, 2.55 kg of industrial hexane (density 680 kg / m ³ ), 137 g of 1,3-butadiene, 43 g of styrene, a mixture of 3- (1-pyrrolidinyl) ethylstyrene and 4- (1-pyrrolidinyl) ethylstyrene. 53 g, 1.52 ml of tetrahydrofuran, and 1.18 ml of ethylene glycol diethyl ether were charged into the polymerization reactor. Next, 3.73 mmol of n-butyllithium was charged into the polymerization reactor as an n-hexane solution to initiate the polymerization reaction.
The stirring speed was 130 rpm, the temperature in the polymerization reactor was 65 ° C., and 1,3-butadiene and styrene, 3- (1-pyrrolidinyl) were continuously fed into the polymerization reactor. ) Copolymerization reaction of ethylstyrene and 4- (1-pyrrolidinyl) ethylstyrene was carried out for 2 hours. The supply amount of 1,3-butadiene was 205 g, and the supply amount of styrene was 65 g. In the total amount of monomers charged and supplied to the polymerization reactor, the charged amount of the mixture of 3- (1-pyrrolidinyl) ethylstyrene and 4- (1-pyrrolidinyl) ethylstyrene was 0.12% by mass.
20 ml of hexane solution containing 0.8 ml of methanol was added to the polymer solution, and the polymer solution was stirred for 5 minutes. Next, 2-tert-butyl-6- (3-tert-butyl-2-hydroxy-5-methylbenzyl) -4-methylphenyl acrylate (manufactured by Sumitomo Chemical Co., Ltd., trade name: Sumilizer GM) was added to the polymer solution. ) 8.0 g, pentaerythrityltetrakis (3-laurylthiopropionate) (Sumitomo Chemical Co., Ltd., trade name: Sumilizer TP-D) 4.0 g was added, and then the polymer solution was cooled to room temperature. Evaporation was performed in 24 hours, and the resultant was further dried under reduced pressure at 55 ° C. for 12 hours to obtain a polymer 12.

(Polymer Production Example 13)
A stainless polymerization reactor with an internal volume of 20 liters equipped with a stirrer was washed, dried and replaced with dry nitrogen. Next, 10.2 kg of industrial hexane (density 680 kg / m ³ ), 608 g of 1,3-butadiene, 192 g of styrene, 1.41 g of 4-vinylpyridine, 6.1 ml of tetrahydrofuran, 4.0 ml of ethylene glycol diethyl ether It was put into the vessel. Next, 2.88 g of bis (diethylamino) methylvinylsilane and an n-hexane solution of n-butyllithium (n-butyllithium content 17.84 mmol) were charged into the polymerization reactor to initiate the polymerization reaction.
The stirring speed was 130 rpm, the temperature in the polymerization reactor was 65 ° C., and 1,3-butadiene, styrene, 4-vinylpyridine and bis were continuously fed while 1,3-butadiene and styrene were continuously fed into the polymerization reactor. The copolymerization reaction of (diethylamino) methylvinylsilane was carried out for 3 hours. The amount of 1,3-butadiene supplied was 912 g, and the amount of styrene supplied was 288 g. Of the total amount of monomers charged and supplied to the polymerization reactor, the amount of 4-vinylpyridine added was 0.07% by mass, and the amount of bis (diethylamino) methylvinylsilane added was 0.14% by mass.
Next, the obtained polymerization reaction solution was stirred at a stirring speed of 130 rpm, 13.4 mmol of [3- (diethylamino) propyl] trimethoxysilane was added to the polymer solution, and further stirred for 15 minutes. Next, 20 ml of hexane solution containing 0.8 ml of methanol was added to the polymer solution, and the polymer solution was further stirred for 5 minutes.
7. 2-tert-butyl-6- (3-tert-butyl-2-hydroxy-5-methylbenzyl) -4-methylphenyl acrylate (manufactured by Sumitomo Chemical Co., Ltd., trade name: Sumilyzer GM) in the polymer solution 0 g, pentaerythrityltetrakis (3-laurylthiopropionate) (Sumitomo Chemical Co., Ltd., trade name: Sumilyzer TP-D) 4.0 g was added, and then the polymer solution was added at room temperature for 24 hours. Evaporated and further dried under reduced pressure at 55 ° C. for 12 hours to obtain a polymer 13.

(Polymer Production Example 14)
A stainless polymerization reactor with an internal volume of 20 liters equipped with a stirrer was washed, dried and replaced with dry nitrogen. Next, 10.2 kg of industrial hexane (density 680 kg / m ³ ), 608 g of 1,3-butadiene, 192 g of styrene, 1.41 g of 4-vinylpyridine, 6.1 ml of tetrahydrofuran, 4.0 ml of ethylene glycol diethyl ether It was put into the vessel. Next, 18.52 mmol of n-butyllithium was charged into the polymerization reactor as an n-hexane solution to initiate the polymerization reaction.
While stirring speed is 130 rpm, polymerization reactor internal temperature is 65 ° C. and 1,3-butadiene and styrene are continuously fed into the polymerization reactor, 1,3-butadiene, styrene, and 4-vinylpyridine The copolymerization reaction of was carried out for 3 hours. The amount of 1,3-butadiene supplied was 912 g, and the amount of styrene supplied was 288 g. Of the total amount of monomers charged / supplied to the polymerization reactor, the amount of 4-vinylpyridine charged was 0.07% by mass.
20 ml of hexane solution containing 0.8 ml of methanol was added to the polymer solution, and the polymer solution was stirred for 5 minutes. Next, 2-tert-butyl-6- (3-tert-butyl-2-hydroxy-5-methylbenzyl) -4-methylphenyl acrylate (manufactured by Sumitomo Chemical Co., Ltd., trade name: Sumilizer GM) was added to the polymer solution. ) 8.0 g, pentaerythrityltetrakis (3-laurylthiopropionate) (Sumitomo Chemical Co., Ltd., trade name: Sumilizer TP-D) 4.0 g was added, and then the polymer solution was cooled to room temperature. Evaporation was performed in 24 hours, and the resultant was further dried under reduced pressure at 55 ° C. for 12 hours to obtain a polymer 14.

(Polymer Production Example 15)
A stainless polymerization reactor with an internal volume of 20 liters equipped with a stirrer was washed, dried and replaced with dry nitrogen. Next, 10.2 kg of industrial hexane (density 680 kg / m ³ ), 608 g of 1,3-butadiene, 192 g of styrene, 2.06 g of 4-N, N-dimethylaminomethylstyrene, 6.1 ml of tetrahydrofuran, ethylene glycol diethyl ether 4.0 ml was charged into the polymerization reactor. Next, 2.74 g of bis (diethylamino) methylvinylsilane and an n-hexane solution of n-butyllithium (content of n-butyllithium 15.90 mmol) were charged into the polymerization reactor to initiate the polymerization reaction. .
The stirring speed was 130 rpm, the temperature in the polymerization reactor was 65 ° C., and 1,3-butadiene, styrene, 4-N, N— were continuously fed into the polymerization reactor while 1,3-butadiene and styrene were continuously fed into the polymerization reactor. A copolymerization reaction of dimethylaminomethylstyrene and bis (diethylamino) methylvinylsilane was performed for 3 hours. The amount of 1,3-butadiene supplied was 912 g, and the amount of styrene supplied was 288 g. Of the total amount of monomers charged / supplied to the polymerization reactor, the amount of 4-N, N-dimethylaminomethylstyrene charged was 0.10% by mass and the amount of bis (diethylamino) methylvinylsilane charged was 0.14%. %Met.
Next, the obtained polymerization reaction solution was stirred at a stirring speed of 130 rpm, 12.80 mmol of N- (3-dimethylaminopropyl) acrylamide was added, and the mixture was stirred for 15 minutes.
20 ml of hexane solution containing 0.8 ml of methanol was added to the polymer solution, and the polymer solution was stirred for 5 minutes. Next, 2-tert-butyl-6- (3-tert-butyl-2-hydroxy-5-methylbenzyl) -4-methylphenyl acrylate (manufactured by Sumitomo Chemical Co., Ltd., trade name: Sumilizer GM) was added to the polymer solution. ) 8.0 g, pentaerythrityltetrakis (3-laurylthiopropionate) (Sumitomo Chemical Co., Ltd., trade name: Sumilizer TP-D) 4.0 g was added. Evaporation was performed in 24 hours, and the resultant was further dried under reduced pressure at 55 ° C. for 12 hours to obtain a polymer 15.

(Polymer Production Example 16)
A stainless polymerization reactor with an internal volume of 20 liters equipped with a stirrer was washed, dried and replaced with dry nitrogen. Next, 10.2 kg of industrial hexane (density 680 kg / m ³ ), 608 g of 1,3-butadiene, 192 g of styrene, 2.04 g of 4-N, N-dimethylaminomethylstyrene, 6.1 ml of tetrahydrofuran, ethylene glycol diethyl ether 4.1 ml was charged into the polymerization reactor. Next, 15.89 mmol of n-butyllithium was charged into the polymerization reactor as an n-hexane solution to start the polymerization reaction.
While stirring speed is 130 rpm, polymerization reactor internal temperature is 65 ° C., and 1,3-butadiene and styrene are continuously fed into the polymerization reactor, 1,3-butadiene, styrene, and 4-N, The copolymerization reaction of N-dimethylaminomethylstyrene was performed for 3 hours. The amount of 1,3-butadiene supplied was 912 g, and the amount of styrene supplied was 288 g. In the total amount of monomers charged / supplied to the polymerization reactor, the amount of 4-N, N-dimethylaminomethylstyrene charged was 0.10% by mass.
20 ml of hexane solution containing 0.8 ml of methanol was added to the polymer solution, and the polymer solution was stirred for 5 minutes. Next, 2-tert-butyl-6- (3-tert-butyl-2-hydroxy-5-methylbenzyl) -4-methylphenyl acrylate (manufactured by Sumitomo Chemical Co., Ltd., trade name: Sumilizer GM) was added to the polymer solution. ) 8.0 g, pentaerythrityltetrakis (3-laurylthiopropionate) (Sumitomo Chemical Co., Ltd., trade name: Sumilizer TP-D) 4.0 g was added, and then the polymer solution was cooled to room temperature. Evaporation was performed in 24 hours, and the resultant was further dried under reduced pressure at 55 ° C. for 12 hours to obtain a polymer 16.

(Polymer Production Example 17)
A stainless polymerization reactor with an internal volume of 20 liters equipped with a stirrer was washed, dried and replaced with dry nitrogen. Next, 10.2 kg of industrial hexane (density 680 kg / m ³ ), 608 g of 1,3-butadiene, 192 g of styrene, 6.1 ml of tetrahydrofuran, and 4.4 ml of ethylene glycol diethyl ether were charged into the polymerization reactor. Next, 2.63 g of bis (diethylamino) methylvinylsilane and an n-hexane solution of n-butyllithium (content of n-butyllithium 14.68 mmol) were charged into the polymerization reactor to initiate the polymerization reaction. .
While stirring speed is 130 rpm, polymerization reactor internal temperature is 65 ° C. and 1,3-butadiene and styrene are continuously fed into the polymerization reactor, 1,3-butadiene, styrene and bis (diethylamino) The copolymerization reaction of methyl vinyl silane was performed for 3 hours. The amount of 1,3-butadiene supplied was 912 g, and the amount of styrene supplied was 288 g. In the total amount of monomers charged / supplied to the polymerization reactor, the charged amount of bis (diethylamino) methylvinylsilane was 0.13% by mass.
20 ml of hexane solution containing 0.8 ml of methanol was added to the polymer solution, and the polymer solution was stirred for 5 minutes. Next, 2-tert-butyl-6- (3-tert-butyl-2-hydroxy-5-methylbenzyl) -4-methylphenyl acrylate (manufactured by Sumitomo Chemical Co., Ltd., trade name: Sumilizer GM) was added to the polymer solution. ) 8.0 g, pentaerythrityltetrakis (3-laurylthiopropionate) (Sumitomo Chemical Co., Ltd., trade name: Sumilizer TP-D) 4.0 g was added, and then the polymer solution was cooled to room temperature. Evaporation was performed in 24 hours, and the resultant was further dried under reduced pressure at 55 ° C. for 12 hours to obtain a polymer 17.

(Polymer Production Example 18)
The inside of the stainless steel polymerization reactor having an internal volume of 20 liters was washed, dried, and replaced with dry nitrogen, and 10.2 kg of industrial hexane (density 680 kg / m ³ ), 547 g of 1,3-butadiene, 173 g of styrene, tetrahydrofuran 6. 07 ml and ethylene glycol diethyl ether 4.12 ml were charged into the polymerization reaction vessel. Next, 13.31 mmol of n-butyllithium was charged into the polymerization reaction vessel as an n-hexane solution to start the polymerization reaction.
The stirring reaction rate is 130 rpm, the temperature in the polymerization reactor is 65 ° C., and the copolymerization reaction of 1,3-butadiene and styrene is performed for 3 hours while continuously supplying 1,3-butadiene and styrene into the polymerization reaction vessel. went. The amount of 1,3-butadiene supplied was 821 g, and the amount of styrene supplied was 259 g.
Next, the obtained polymerization reaction solution was stirred at a stirring speed of 130 rpm, 11.25 mmol of N- (3-dimethylaminopropyl) acrylamide was added, and the mixture was stirred for 15 minutes.
To the polymerization reaction solution, 20 ml of a hexane solution containing 1.12 ml of methanol was added, and the polymerization reaction solution was further stirred for 5 minutes.
7. 2-tert-butyl-6- (3-tert-butyl-2-hydroxy-5-methylbenzyl) -4-methylphenyl acrylate (manufactured by Sumitomo Chemical Co., Ltd., trade name: Sumilyzer GM) in the polymerization reaction solution 0 g, pentaerythrityltetrakis (3-lauryl thiopropionate) (Sumitomo Chemical Co., Ltd., trade name: Sumilizer TP-D) 4.0 g was added, and then the polymerization reaction solution was added at room temperature for 24 hours. Evaporated and further dried under reduced pressure at 55 ° C. for 12 hours to obtain polymer 18.

(Polymer Production Example 19)
A stainless polymerization reactor with an internal volume of 20 liters equipped with a stirrer was washed, dried and replaced with dry nitrogen. Next, 10.2 kg of industrial hexane (density 680 kg / m ³ ), 608 g of 1,3-butadiene, 192 g of styrene, 3.37 g of 4-bis (trimethylsilyl) aminostyrene, 6.1 ml of tetrahydrofuran, ethylene glycol diethyl ether 4. 0 ml was charged into the polymerization reactor. Next, 2.74 g of bis (diethylamino) methylvinylsilane and an n-hexane solution of n-butyllithium (content of n-butyllithium 15.55 mmol) were charged into the polymerization reactor to initiate the polymerization reaction. .
1,3-butadiene, styrene, 4-bis (trimethylsilyl), while stirring speed is 130 rpm, polymerization reactor temperature is 65 ° C., and 1,3-butadiene and styrene are continuously fed into the polymerization reactor. A copolymerization reaction of aminostyrene and bis (diethylamino) methylvinylsilane was carried out for 3 hours. The amount of 1,3-butadiene supplied was 912 g, and the amount of styrene supplied was 288 g. In the total amount of monomers charged / supplied to the polymerization reactor, the charged amount of 4-bis (trimethylsilyl) aminostyrene was 0.17% by mass, and the charged amount of bis (diethylamino) methylvinylsilane was 0.14% by mass. there were.
Next, the obtained polymerization reaction solution was stirred at a stirring speed of 130 rpm, 12.80 mmol of N- (3-dimethylaminopropyl) acrylamide was added, and the mixture was stirred for 15 minutes.
20 ml of hexane solution containing 0.8 ml of methanol was added to the polymer solution, and the polymer solution was stirred for 5 minutes. Next, 2-tert-butyl-6- (3-tert-butyl-2-hydroxy-5-methylbenzyl) -4-methylphenyl acrylate (manufactured by Sumitomo Chemical Co., Ltd., trade name: Sumilizer GM) was added to the polymer solution. ) 8.0 g, pentaerythrityltetrakis (3-laurylthiopropionate) (Sumitomo Chemical Co., Ltd., trade name: Sumilizer TP-D) 4.0 g was added, and then the polymer solution was cooled to room temperature. Evaporation was performed in 24 hours, and the resultant was further dried under reduced pressure at 55 ° C. for 12 hours to obtain a polymer 19.

(Polymer Production Example 20)
The inside of the stainless steel polymerization reactor with an internal volume of 5 liters equipped with a stirrer was washed, dried and replaced with dry nitrogen. Next, 2.55 kg of industrial hexane (density 680 kg / m ³ ), 137 g of 1,3-butadiene, 43 g of styrene, 0.70 g of 4-bis (trimethylsilyl) aminostyrene, 1.52 ml of tetrahydrofuran, ethylene glycol diethyl ether 18 ml was charged into the polymerization reactor. Next, 3.81 mmol of n-butyllithium was charged into the polymerization reactor as an n-hexane solution to initiate the polymerization reaction.
While the stirring speed was 130 rpm, the temperature in the polymerization reactor was 65 ° C., and 1,3-butadiene and styrene were continuously fed into the polymerization reactor, 1,3-butadiene, styrene, and 4-bis ( The copolymerization reaction of trimethylsilyl) aminostyrene was carried out for 2 hours. The supply amount of 1,3-butadiene was 205 g, and the supply amount of styrene was 65 g. In the total amount of monomers charged and supplied to the polymerization reactor, the amount of 4-bis (trimethylsilyl) aminostyrene charged was 0.16% by mass.
10 ml of hexane solution containing 0.5 ml of methanol was added to the polymer solution, and the polymer solution was stirred for 5 minutes. Next, 2-tert-butyl-6- (3-tert-butyl-2-hydroxy-5-methylbenzyl) -4-methylphenyl acrylate (manufactured by Sumitomo Chemical Co., Ltd., trade name: Sumilizer GM) was added to the polymer solution. ) 1.8 g, pentaerythrityltetrakis (3-laurylthiopropionate) (Sumitomo Chemical Co., Ltd., trade name: Sumilizer TP-D) 0.9 g was added, and then the polymer solution was cooled to room temperature. Evaporation was performed in 24 hours, and the resultant was further dried under reduced pressure at 55 ° C. for 12 hours to obtain a polymer 20.

(Polymer Production Example 21)
The inside of a stainless steel polymerization reactor having an internal volume of 20 liters was washed, dried and replaced with dry nitrogen, and 10.2 kg of industrial hexane (density 680 Kg / m ³ ), 608 g of 1,3-butadiene, 192 g of styrene, tetrahydrofuran 6. 07 ml and ethylene glycol diethyl ether 4.00 ml were charged into the polymerization reaction vessel. Next, 12.70 mmol of dimethyl-1-piperidinylmethylvinylsilane and 14.59 mmol of n-butyllithium were added as an n-hexane solution to initiate polymerization.
While stirring speed was 130 rpm, polymerization reactor internal temperature was 65 ° C., and monomers were continuously fed into the polymerization reaction vessel, 1,3-butadiene, styrene, and dimethyl-1-piperidinylmethylvinylsilane Copolymerization was carried out for 3.0 hours. The amount of 1,3-butadiene supplied during the entire polymerization was 912 g, and the amount of styrene supplied was 288 g.
Next, 20 ml of a hexane solution containing 0.77 ml of methanol was added to the obtained polymerization reaction solution, and the polymerization reaction solution was further stirred for 5 minutes.
6. 2-tert-butyl-6- (3-tert-butyl-2-hydroxy-5-methylbenzyl) -4-methylphenyl acrylate (manufactured by Sumitomo Chemical Co., Ltd., trade name: Sumilyzer GM) in the polymerization reaction solution 2 g, 3.6 g of pentaerythrityltetrakis (3-laurylthiopropionate) (manufactured by Sumitomo Chemical Co., Ltd., trade name: Sumilizer TP-D) was added, and then the polymerization reaction solution was allowed to stand at room temperature for 24 hours. Evaporated and further dried under reduced pressure at 55 ° C. for 12 hours to obtain a polymer 21.

(Polymer Production Example 22)
The inside of a stainless steel polymerization reactor having an internal volume of 5 liters was washed, dried and replaced with dry nitrogen, 2.55 kg of industrial hexane (density 680 Kg / m ³ ), 137 g of 1,3-butadiene, 43 g of styrene, tetrahydrofuran 1. 52 ml and 1.12 ml of ethylene glycol diethyl ether were charged into the polymerization reaction vessel. Next, 8.70 mmol of dimethyl-1-piperidinylmethylvinylsilane and 3.37 mmol of n-butyllithium were added as an n-hexane solution to initiate polymerization.
While stirring speed was 130 rpm, polymerization reactor internal temperature was 65 ° C., and monomers were continuously fed into the polymerization reaction vessel, 1,3-butadiene, styrene, and dimethyl-1-piperidinylmethylvinylsilane Copolymerization was carried out for 2.5 hours. The supply amount of 1,3-butadiene in the entire polymerization was 205 g, and the supply amount of styrene was 65 g. The polymerization conversion rate was almost 100%.
To the polymerization reaction solution, 10 ml of hexane solution containing 0.20 ml of methanol was added, and the polymerization reaction solution was further stirred for 5 minutes.
2-tert-butyl-6- (3-tert-butyl-2-hydroxy-5-methylbenzyl) -4-methylphenyl acrylate (manufactured by Sumitomo Chemical Co., Ltd., trade name: Sumilyzer GM) was added to the polymerization reaction solution. 8 g, 0.9 g of pentaerythrityltetrakis (3-laurylthiopropionate) (manufactured by Sumitomo Chemical Co., Ltd., trade name: Sumilizer TP-D) was added, and then the polymerization reaction solution was added at room temperature for 24 hours. Evaporated and further dried under reduced pressure at 55 ° C. for 12 hours to obtain a polymer 22.

(Polymer Production Example 23)
The inside of the stainless steel polymerization reactor having an internal volume of 20 liters was washed, dried and replaced with dry nitrogen, and 10.2 kg of industrial hexane (density 680 Kg / m ³ ), 547 g of 1,3-butadiene, 173 g of styrene, tetrahydrofuran 6. 07 ml and ethylene glycol diethyl ether 4.00 ml were charged into the polymerization reaction vessel. Next, 14.46 mmol of n-butyllithium was added as an n-hexane solution to initiate polymerization.
The stirring rate was 130 rpm, the temperature in the polymerization reactor was 65 ° C., and 1,3-butadiene and styrene were copolymerized for 3 hours while continuously supplying the monomer into the polymerization reaction vessel. The supply amount of 1,3-butadiene in the total polymerization was 821 g, and the supply amount of styrene was 259 g.
10 ml of hexane solution containing 0.75 ml of methanol was added to the polymerization reaction solution, and the polymerization reaction solution was further stirred for 5 minutes.
7. 2-tert-butyl-6- (3-tert-butyl-2-hydroxy-5-methylbenzyl) -4-methylphenyl acrylate (manufactured by Sumitomo Chemical Co., Ltd., trade name: Sumilyzer GM) in the polymerization reaction solution 0 g, pentaerythrityltetrakis (3-lauryl thiopropionate) (Sumitomo Chemical Co., Ltd., trade name: Sumilizer TP-D) 4.0 g was added, and then the polymerization reaction solution was added at room temperature for 24 hours. Evaporated and further dried under reduced pressure at 55 ° C. for 12 hours to obtain a polymer 23.

(Polymer Production Example 24)
The inside of the stainless steel polymerization reactor with an internal volume of 5 liters equipped with a stirrer was washed, dried and replaced with dry nitrogen. Next, 2.55 kg of industrial hexane (density 680 kg / m ³ ), 1,3-butadiene 137 g, styrene 43 g, tert-butoxydiphenylvinylsilane 0.81 g, tetrahydrofuran 1.52 ml, ethylene glycol diethyl ether 1.18 ml were polymerized. Charged into the reactor. Next, 2.88 mmol of n-butyllithium was charged into the polymerization reactor as an n-hexane solution to start the polymerization reaction.

While the stirring speed is 130 rpm, the temperature in the polymerization reactor is 65 ° C., and the monomer is continuously fed into the polymerization reactor, the copolymerization of 1,3-butadiene, styrene, and tert-butoxydiphenylvinylsilane is performed 2 Went for hours. The supply amount of 1,3-butadiene was 205 g, and the supply amount of styrene was 65 g. In addition, in the total amount of monomers charged / supplied to the polymerization reactor, the charged amount of tert-butoxydiphenylvinylsilane was 0.18% by weight.

10 ml of a hexane solution containing 0.2 ml of methanol was added to the polymer solution, and the polymer solution was further stirred for 5 minutes.

2-tert-butyl-6- (3-tert-butyl-2-hydroxy-5-methylbenzyl) -4-methylphenyl acrylate (manufactured by Sumitomo Chemical Co., Ltd., trade name: Sumilyzer GM) was added to the polymer solution. 8 g, 0.9 g of pentaerythrityltetrakis (3-laurylthiopropionate) (manufactured by Sumitomo Chemical Co., Ltd., trade name: Sumilizer TP-D) was added, and then the polymer solution was stirred at room temperature for 24 hours. Evaporated and further dried under reduced pressure at 55 ° C. for 12 hours to obtain a polymer 24.

(Polymer Production Example 25)
A stainless polymerization reactor with an internal volume of 20 liters equipped with a stirrer was washed, dried and replaced with dry nitrogen. Next, 10.2 kg of industrial hexane (density 680 kg / m ³ ), 608 g of 1,3-butadiene, 192 g of styrene, 6.1 ml of tetrahydrofuran, and 4.0 ml of ethylene glycol diethyl ether were charged into the polymerization reactor. Next, 12.40 mmol of n-butyllithium was charged into the polymerization reactor as an n-hexane solution to initiate the polymerization reaction.

The copolymerization reaction of 1,3-butadiene and styrene was carried out for 3 hours while the stirring speed was 130 rpm, the temperature in the polymerization reactor was 65 ° C., and the monomer was continuously fed into the polymerization reactor. The amount of 1,3-butadiene supplied was 912 g, and the amount of styrene supplied was 288 g. 20 ml of hexane solution containing 0.8 ml of methanol was added to the polymer solution, and the polymer solution was further stirred for 5 minutes.

7. 2-tert-butyl-6- (3-tert-butyl-2-hydroxy-5-methylbenzyl) -4-methylphenyl acrylate (manufactured by Sumitomo Chemical Co., Ltd., trade name: Sumilyzer GM) in the polymer solution 0 g, pentaerythrityltetrakis (3-laurylthiopropionate) (Sumitomo Chemical Co., Ltd., trade name: Sumilyzer TP-D) 4.0 g was added, and then the polymer solution was added at room temperature for 24 hours. Evaporated and further dried under reduced pressure at 55 ° C. for 12 hours to obtain a polymer 25.

(Polymer Production Example 26)
A stainless steel polymerization reactor having an internal volume of 20 liters was washed, dried, and substituted with dry nitrogen, and then 1,3-butadiene 1404 g, styrene 396 g, tetrahydrofuran 328 g, hexane 10.2 kg, n-butyllithium (n-hexane solution 15 0.0 mmol) was added and polymerization was carried out at 65 ° C. for 3 hours with stirring. After completion of the polymerization, 7.5 mmol (2.23 g) of triglycidyl isocyanurate was added. After reacting at 65 ° C. for 30 minutes with stirring, 10 ml of methanol was added, and the mixture was further stirred for 5 minutes. Thereafter, the contents of the polymerization reaction vessel are taken out, 10 g of 2,6-di-t-butyl-p-cresol (Sumitomo Chemical Co., Ltd., Sumitizer BHT: the same applies below) is added, and most of the hexane is evaporated. Then, it was dried under reduced pressure at 55 ° C. for 12 hours to obtain a polymer 26.

(Polymer Production Example 27)
A stainless steel polymerization reactor having an internal volume of 20 liters was washed, dried, and substituted with dry nitrogen, and then 1,3-butadiene 1404 g, styrene 396 g, tetrahydrofuran 328 g, hexane 10.2 kg, n-butyllithium (n-hexane solution 8 0.5 mmol) was added, and polymerization was carried out at 65 ° C. for 3 hours with stirring. After completion of the polymerization, 0.16 mmol (0.027 g) of silicon tetrachloride was added, and the mixture was reacted at 65 ° C. for 15 minutes with stirring. Further, instead of triglycidyl isocyanurate, 7.65 mmol (1.19 g) of N, N-dimethylaminopropylacrylamide was added, and the mixture was reacted at 65 ° C. for 30 minutes with stirring, and then 10 ml of methanol was added. Stir for another 5 minutes. Thereafter, the content of the polymerization reaction vessel is taken out, 10 g of 2,6-di-t-butyl-p-cresol (Sumitomo Chemical Co., Ltd., Sumitizer BHT: the same applies hereinafter) is added, and most of the hexane is evaporated. Then, it was dried under reduced pressure at 55 ° C. for 12 hours to obtain a polymer 27.

(Polymer Production Example 28)
The n-butyllithium solution in n-hexane was changed to 8.7 mmol, the silicon tetrachloride was changed to 0.17 mmol (0.029 g), and triglycidyl isocyanurate and N, N-dimethylaminopropylacrylamide were added. Except not having added, it carried out similarly to the polymer manufacture example 27, and the polymer 28 was obtained.

(Polymer Production Example 29)
A stainless polymerization reactor with an internal volume of 20 liters equipped with a stirrer was washed, dried and replaced with dry nitrogen. Next, 10.2 kg of industrial hexane (density 680 kg / m ³ ), 608 g of 1,3-butadiene, 192 g of styrene, 2.58 g of a mixture of 4-pyrrolidinoethylstyrene and 3-pyrrolidinoethylstyrene, 6.1 ml of tetrahydrofuran Then, 4.0 ml of ethylene glycol diethyl ether was charged into the polymerization reactor. Next, 15.08 mmol of n-butyllithium was charged into the polymerization reactor as an n-hexane solution to initiate the polymerization reaction.

1,3-butadiene, styrene, 4-pyrrolidinoethyl styrene while stirring speed is 130 rpm, polymerization reactor temperature is 65 ° C., and 1,3-butadiene and styrene are continuously fed into the polymerization reactor. And 3-pyrrolidinoethylstyrene copolymerization reaction was carried out for 3 hours. The amount of 1,3-butadiene supplied was 912 g, and the amount of styrene supplied was 288 g. The total amount of 4-pyrrolidinoethylstyrene and 3-pyrrolidinoethylstyrene charged in the total amount of monomers charged / supplied to the polymerization reactor was 0.13% by weight.

Next, the obtained polymer solution was stirred at a stirring speed of 130 rpm, 12.8 mmol of [3- (diethylamino) propyl] trimethoxysilane was added to the polymer solution, and further stirred for 15 minutes. Next, 20 ml of hexane solution containing 0.8 ml of methanol was added to the polymer solution, and the polymer solution was further stirred for 5 minutes.

7. 2-tert-butyl-6- (3-tert-butyl-2-hydroxy-5-methylbenzyl) -4-methylphenyl acrylate (manufactured by Sumitomo Chemical Co., Ltd., trade name: Sumilyzer GM) in the polymer solution 0 g, pentaerythrityltetrakis (3-laurylthiopropionate) (Sumitomo Chemical Co., Ltd., trade name: Sumilyzer TP-D) 4.0 g was added, and then the polymer solution was added at room temperature for 24 hours. Evaporated and further dried under reduced pressure at 55 ° C. for 12 hours to obtain a polymer 29.

(Polymer Production Example 30)
A stainless polymerization reactor with an internal volume of 20 liters equipped with a stirrer was washed, dried and replaced with dry nitrogen. Next, 10.2 kg of industrial hexane (density 680 kg / m ³ ), 608 g of 1,3-butadiene, 192 g of styrene, 7.73 g of a mixture of 4-pyrrolidinoethylstyrene and 3-pyrrolidinoethylstyrene, 6.1 ml of tetrahydrofuran Then, 4.0 ml of ethylene glycol diethyl ether was charged into the polymerization reactor. Next, 15.38 mmol of n-butyllithium was charged into the polymerization reactor as an n-hexane solution to initiate the polymerization reaction.

1,3-butadiene, styrene, 4-pyrrolidinoethyl styrene while stirring speed is 130 rpm, polymerization reactor temperature is 65 ° C., and 1,3-butadiene and styrene are continuously fed into the polymerization reactor. And 3-pyrrolidinoethylstyrene copolymerization reaction was carried out for 3 hours. The amount of 1,3-butadiene supplied was 912 g, and the amount of styrene supplied was 288 g. The total amount of 4-pyrrolidinoethylstyrene and 3-pyrrolidinoethylstyrene charged in the total amount of monomers charged / supplied to the polymerization reactor was 0.39% by weight.

Next, the obtained polymer solution was stirred at a stirring speed of 130 rpm, 12.8 mmol of [3- (diethylamino) propyl] trimethoxysilane was added to the polymer solution, and further stirred for 15 minutes. Next, 20 ml of hexane solution containing 0.8 ml of methanol was added to the polymer solution, and the polymer solution was further stirred for 5 minutes.

7. 2-tert-butyl-6- (3-tert-butyl-2-hydroxy-5-methylbenzyl) -4-methylphenyl acrylate (manufactured by Sumitomo Chemical Co., Ltd., trade name: Sumilyzer GM) in the polymer solution 0 g, pentaerythrityltetrakis (3-laurylthiopropionate) (Sumitomo Chemical Co., Ltd., trade name: Sumilyzer TP-D) 4.0 g was added, and then the polymer solution was added at room temperature for 24 hours. Evaporated and further dried under reduced pressure at 55 ° C. for 12 hours to obtain a polymer 30.

(Polymer Production Example 31)
A stainless polymerization reactor with an internal volume of 20 liters equipped with a stirrer was washed, dried, and replaced with dry nitrogen. Next, 10.2 kg of industrial hexane (density 680 kg / m ³ ), 547 g of 1,3-butadiene, 173 g of styrene, 6.1 ml of tetrahydrofuran, and 4.7 ml of ethylene glycol diethyl ether were charged into the polymerization reactor. Next, 15.38 mmol of n-butyllithium was charged into the polymerization reactor as an n-hexane solution to initiate the polymerization reaction.

The stirring reaction rate is 130 rpm, the temperature in the polymerization reactor is 65 ° C., and the copolymerization reaction of 1,3-butadiene and styrene is performed for 3 hours while continuously supplying 1,3-butadiene and styrene into the polymerization reactor. went. The amount of 1,3-butadiene supplied was 821 g, and the amount of styrene supplied was 259 g.

Next, the obtained polymer solution was stirred at a stirring speed of 130 rpm, and 12.80 mmol of [3- (diethylamino) propyl] trimethoxysilane was added and stirred for 15 minutes. 20 ml of a hexane solution containing 0.8 ml of methanol in the polymer solution was added to the polymer solution, and the polymer solution was further stirred for 5 minutes.

7. 2-tert-butyl-6- (3-tert-butyl-2-hydroxy-5-methylbenzyl) -4-methylphenyl acrylate (manufactured by Sumitomo Chemical Co., Ltd., trade name: Sumilyzer GM) in the polymer solution 0 g, pentaerythrityltetrakis (3-laurylthiopropionate) (Sumitomo Chemical Co., Ltd., trade name: Sumilyzer TP-D) 4.0 g was added, and then the polymer solution was added at room temperature for 24 hours. Evaporated and further dried under reduced pressure at 55 ° C. for 12 hours to obtain a polymer 31.

(Polymer Production Example 32)
The inside of the stainless steel polymerization reactor with an internal volume of 5 liters equipped with a stirrer was washed, dried and replaced with dry nitrogen. Next, 2.55 kg of industrial hexane (density 680 kg / m ³ ), 137 g of 1,3-butadiene, 43 g of styrene, 0.53 g of a mixture of 4-pyrrolidinoethylstyrene and 3-pyrrolidinoethylstyrene, 1.52 ml of tetrahydrofuran Then, 1.18 ml of ethylene glycol diethyl ether was charged into the polymerization reactor. Next, 3.73 mmol of n-butyllithium was charged into the polymerization reactor as an n-hexane solution to initiate the polymerization reaction.

1,3-butadiene, styrene, 4-pyrrolidinoethyl styrene while stirring speed is 130 rpm, polymerization reactor temperature is 65 ° C., and 1,3-butadiene and styrene are continuously fed into the polymerization reactor. And a copolymerization reaction with 3-pyrrolidinoethylstyrene was carried out for 2 hours. The supply amount of 1,3-butadiene was 205 g, and the supply amount of styrene was 65 g. The total amount of 4-pyrrolidinoethylstyrene and 3-pyrrolidinoethylstyrene charged in the total amount of monomers charged / supplied to the polymerization reactor was 0.12% by weight. 10 ml of a hexane solution containing 0.5 ml of methanol was added to the polymer solution, and the polymer solution was further stirred for 5 minutes.

2-tert-butyl-6- (3-tert-butyl-2-hydroxy-5-methylbenzyl) -4-methylphenyl acrylate (manufactured by Sumitomo Chemical Co., Ltd., trade name: Sumilyzer GM) was added to the polymer solution. 8 g, 0.9 g of pentaerythrityltetrakis (3-laurylthiopropionate) (manufactured by Sumitomo Chemical Co., Ltd., trade name: Sumilizer TP-D) was added, and then the polymer solution was stirred at room temperature for 24 hours. Evaporated and further dried under reduced pressure at 55 ° C. for 12 hours to obtain a polymer 32.

(Polymer Production Example 33)
A stainless polymerization reactor with an internal volume of 20 liters equipped with a stirrer was washed, dried and replaced with dry nitrogen. Next, 10.2 kg of industrial hexane (density 680 kg / m ³ ), 608 g of 1,3-butadiene, 192 g of styrene, 1.41 g of 4-vinylpyridine, 6.1 ml of tetrahydrofuran, 4.0 ml of ethylene glycol diethyl ether It was put into the vessel. Next, 18.26 mmol of n-butyllithium was charged into the polymerization reactor as an n-hexane solution to initiate the polymerization reaction.

While stirring speed is 130 rpm, polymerization reactor internal temperature is 65 ° C. and 1,3-butadiene and styrene are continuously fed into the polymerization reactor, 1,3-butadiene, styrene, and 4-vinylpyridine The copolymerization reaction of was carried out for 3 hours. The amount of 1,3-butadiene supplied was 912 g, and the amount of styrene supplied was 288 g. Of the total amount of monomers charged / supplied to the polymerization reactor, the amount of 4-vinylpyridine charged was 0.07% by mass.

Next, the obtained polymer solution was stirred at a stirring speed of 130 rpm, and 13.42 mmol of [3- (diethylamino) propyl] trimethoxysilane was added to the polymer solution, and further stirred for 15 minutes. Next, 20 ml of hexane solution containing 0.8 ml of methanol was added to the polymer solution, and the polymer solution was further stirred for 5 minutes.

7. 2-tert-butyl-6- (3-tert-butyl-2-hydroxy-5-methylbenzyl) -4-methylphenyl acrylate (manufactured by Sumitomo Chemical Co., Ltd., trade name: Sumilyzer GM) in the polymer solution 0 g, pentaerythrityltetrakis (3-laurylthiopropionate) (Sumitomo Chemical Co., Ltd., trade name: Sumilyzer TP-D) 4.0 g was added, and then the polymer solution was added at room temperature for 24 hours. Evaporated and further dried under reduced pressure at 55 ° C. for 12 hours to obtain a polymer 33.

(Polymer Production Example 34)
A stainless polymerization reactor with an internal volume of 20 liters equipped with a stirrer was washed, dried and replaced with dry nitrogen. Next, 10.2 kg of industrial hexane (density 680 kg / m ³ ), 608 g of 1,3-butadiene, 192 g of styrene, 4.18 g of 4-vinylpyridine, 6.1 ml of tetrahydrofuran, 4.0 ml of ethylene glycol diethyl ether It was put into the vessel. Next, 22.62 mmol of n-butyllithium was charged into the polymerization reactor as an n-hexane solution to start the polymerization reaction.

While stirring speed is 130 rpm, polymerization reactor internal temperature is 65 ° C. and 1,3-butadiene and styrene are continuously fed into the polymerization reactor, 1,3-butadiene, styrene, and 4-vinylpyridine The copolymerization reaction of was carried out for 3 hours. The amount of 1,3-butadiene supplied was 912 g, and the amount of styrene supplied was 288 g. Of the total amount of monomers charged / supplied to the polymerization reactor, the amount of 4-vinylpyridine charged was 0.21% by mass.

Next, the obtained polymer solution was stirred at a stirring speed of 130 rpm, 13.26 mmol of [3- (diethylamino) propyl] trimethoxysilane was added to the polymer solution, and further stirred for 15 minutes. Next, 20 ml of hexane solution containing 0.8 ml of methanol was added to the polymer solution, and the polymer solution was further stirred for 5 minutes.

7. 2-tert-butyl-6- (3-tert-butyl-2-hydroxy-5-methylbenzyl) -4-methylphenyl acrylate (manufactured by Sumitomo Chemical Co., Ltd., trade name: Sumilyzer GM) in the polymer solution 0 g, pentaerythrityltetrakis (3-laurylthiopropionate) (Sumitomo Chemical Co., Ltd., trade name: Sumilyzer TP-D) 4.0 g was added, and then the polymer solution was added at room temperature for 24 hours. Evaporated and further dried under reduced pressure at 55 ° C. for 12 hours to obtain a polymer 34.

(Polymer Production Example 35)
A stainless polymerization reactor with an internal volume of 20 liters equipped with a stirrer was washed, dried, and replaced with dry nitrogen. Next, 10.2 kg of industrial hexane (density 680 kg / m ³ ), 547 g of 1,3-butadiene, 173 g of styrene, 6.1 ml of tetrahydrofuran, and 4.7 ml of ethylene glycol diethyl ether were charged into the polymerization reactor. Next, 15.38 mmol of n-butyllithium was charged into the polymerization reactor as an n-hexane solution to initiate the polymerization reaction.

The stirring reaction rate is 130 rpm, the temperature in the polymerization reactor is 65 ° C., and the copolymerization reaction of 1,3-butadiene and styrene is performed for 3 hours while continuously supplying 1,3-butadiene and styrene into the polymerization reactor. went. The amount of 1,3-butadiene supplied was 821 g, and the amount of styrene supplied was 259 g.

Next, the obtained polymer solution was stirred at a stirring speed of 130 rpm, and 12.80 mmol of [3- (diethylamino) propyl] trimethoxysilane was added and stirred for 15 minutes. 20 ml of a hexane solution containing 0.8 ml of methanol in the polymer solution was added to the polymer solution, and the polymer solution was further stirred for 5 minutes.

7. 2-tert-butyl-6- (3-tert-butyl-2-hydroxy-5-methylbenzyl) -4-methylphenyl acrylate (manufactured by Sumitomo Chemical Co., Ltd., trade name: Sumilyzer GM) in the polymer solution 0 g, pentaerythrityltetrakis (3-laurylthiopropionate) (Sumitomo Chemical Co., Ltd., trade name: Sumilyzer TP-D) 4.0 g was added, and then the polymer solution was added at room temperature for 24 hours. Evaporated and further dried under reduced pressure at 55 ° C. for 12 hours to obtain a polymer 35.

(Polymer Production Example 36)
A stainless polymerization reactor with an internal volume of 20 liters equipped with a stirrer was washed, dried and replaced with dry nitrogen. Next, 10.2 kg of industrial hexane (density 680 kg / m ³ ), 608 g of 1,3-butadiene, 192 g of styrene, 1.41 g of 4-vinylpyridine, 6.1 ml of tetrahydrofuran, 4.0 ml of ethylene glycol diethyl ether It was put into the vessel. Next, 18.52 mmol of n-butyllithium was charged into the polymerization reactor as an n-hexane solution to initiate the polymerization reaction.

While stirring speed is 130 rpm, polymerization reactor internal temperature is 65 ° C. and 1,3-butadiene and styrene are continuously fed into the polymerization reactor, 1,3-butadiene, styrene, and 4-vinylpyridine The copolymerization reaction of was carried out for 3 hours. The amount of 1,3-butadiene supplied was 912 g, and the amount of styrene supplied was 288 g. Of the total amount of monomers charged / supplied to the polymerization reactor, the amount of 4-vinylpyridine charged was 0.07% by mass.

Next, the obtained polymer solution was stirred at a stirring speed of 130 rpm, 20 ml of a hexane solution containing 0.8 ml of methanol was added to the polymer solution, and the polymer solution was further stirred for 5 minutes.

7. 2-tert-butyl-6- (3-tert-butyl-2-hydroxy-5-methylbenzyl) -4-methylphenyl acrylate (manufactured by Sumitomo Chemical Co., Ltd., trade name: Sumilyzer GM) in the polymer solution 0 g, pentaerythrityltetrakis (3-laurylthiopropionate) (Sumitomo Chemical Co., Ltd., trade name: Sumilyzer TP-D) 4.0 g was added, and then the polymer solution was added at room temperature for 24 hours. Evaporated and further dried under reduced pressure at 55 ° C. for 12 hours to obtain a polymer 36.

The obtained polymers 1 to 36 were analyzed by the following method. The results are shown in Tables 1-8.

<Mooney viscosity (ML _{1 + 4} )>
The Mooney viscosity of the copolymer was measured at 100 ° C. according to JIS K6300 (1994).

<Amount of vinyl (unit: mol%)>
The amount of vinyl in the copolymer was determined from the absorption intensity in the vicinity of 910 cm ^−1, which is the vinyl group absorption peak, by infrared spectroscopy.

<Styrene amount (unit: mass%)>
According to JIS K6383 (1995), the styrene content of the copolymer was determined from the refractive index.

<Molecular weight distribution (Mw / Mn)>
The weight average molecular weight (Mw) and the number average molecular weight (Mn) are measured by gel permeation chromatography (GPC) method under the following conditions (1) to (8), and the molecular weight distribution (Mw) of the copolymer is measured. / Mn).
(1) Apparatus: HLC-8220 manufactured by Tosoh Corporation
(2) Separation column: HM-H manufactured by Tosoh Corporation (two in series)
(3) Measurement temperature: 40 ° C
(4) Carrier: Tetrahydrofuran (5) Flow rate: 0.6 mL / min (6) Injection volume: 5 μL
(7) Detector: Differential refraction (8) Molecular weight standard: Standard polystyrene

Below, various chemical | medical agents used by the Example and the comparative example are demonstrated.
Natural rubber (NR): RSS # 3
Butadiene rubber (BR): Ubepol BR150B manufactured by Ube Industries, Ltd.
Polymers 1-36: Synthetic conductive carbon black in Production Examples 1-36 above: Seest 50 (average particle size: 43 nm, N ₂ SA: 42 m ² / g, DBP oil absorption: 115 ml, manufactured by Tokai Carbon Co., Ltd. / 100 g, iodine adsorption amount: 44 cm ² / g)
Conductive carbon black 2: Acetylene black (N ₂ SA: 68 m ² / g, DBP oil absorption: 175 ml / 100 g) manufactured by Denki Kagaku Kogyo Co., Ltd.
Carbon black (general carbon black): Dia Black N220 (N ₂ SA: 111 m ² / g, DBP absorption: 115 ml / 100 g) manufactured by Mitsubishi Chemical Corporation
Silica: Ultrasil VN3 manufactured by Degussa (N ₂ SA: 175 m ² / g)
Silane coupling agent: Si69 (bis (3-triethoxysilylpropyl) tetrasulfide) manufactured by Degussa
Anti-aging agent: Antigen 3C manufactured by Sumitomo Chemical Co., Ltd.
Wax: Sunnock N manufactured by Ouchi Shinsei Chemical Industry Co., Ltd.
Oil: X-140 manufactured by Japan Energy Co., Ltd.
Stearic acid: Beads manufactured by NOF Corporation Zinc stearate zinc oxide: Zinc flower No. 1 manufactured by Mitsui Mining & Smelting Co., Ltd. Sulfur: Powder sulfur vulcanization accelerator manufactured by Tsurumi Chemical Co., Ltd. 1: Sumitomo Chemical ( Soxinol CZ manufactured by
Vulcanization accelerator 2: Soxinol D manufactured by Sumitomo Chemical Co., Ltd.

<Examples and Comparative Examples>
According to the blending contents shown in Tables 9 to 16, materials other than sulfur and a vulcanization accelerator were kneaded for 5 minutes at 150 ° C. using a 1.7 L Banbury mixer manufactured by Kobe Steel Co., Ltd., and mixed. A kneaded paste was obtained. Next, sulfur and a vulcanization accelerator were added to the obtained kneaded product, and kneaded for 5 minutes under the condition of 80 ° C. using an open roll to obtain an unvulcanized rubber composition. The obtained unvulcanized rubber composition was press vulcanized with a 0.5 mm thick mold at 170 ° C. for 20 minutes to obtain a vulcanized rubber composition.
Further, the obtained unvulcanized rubber composition is molded into a tread shape and bonded together with other tire members on a tire molding machine to form an unvulcanized tire, which is vulcanized at 170 ° C. for 12 minutes, and tested. Tires (size: 195 / 65R15) were manufactured.

The following evaluation was performed about the obtained vulcanized rubber composition and the tire for a test. The results are shown in Tables 9-16. In the following evaluation, the reference comparative example in Table 9 is Comparative Example 1, the reference comparative example in Table 10 is Comparative Example 16, the reference comparative example in Table 11 is Comparative Example 29, and the reference comparative example in Table 12 is Comparative Example 42. The reference comparative example in Table 13 was designated as Comparative Example 49, the reference comparative example in Table 14 as Comparative Example 55, the reference comparative example in Table 15 as Comparative Example 62, and the reference comparative example in Table 16 as Comparative Example 71.

<Evaluation items and test methods>
(Tan δ)
A strip-shaped test piece having a width of 1 mm or 2 mm and a length of 40 mm was punched out from the sheet-like vulcanized rubber composition and subjected to the test. Using a spectrometer manufactured by Ueshima Seisakusho, tan δ was measured at a dynamic strain amplitude of 1%, a frequency of 10 Hz, and a temperature of 70 ° C. The reciprocal value of tan δ was expressed as an index with the reference comparative example being 100. The larger the value, the lower the rolling resistance and the lower the fuel consumption.

(Rolling resistance)
Using a rolling resistance tester, the rolling resistance when the test tire was run at a rim (15 × 6JJ), internal pressure (230 kPa), load (3.43 kN), speed (80 km / h) was measured, and the standard The index was expressed as an index when the comparative example was 100. A larger index is better (low fuel consumption).

(Wet grip performance)
Each test tire was mounted on all wheels of a vehicle (domestic FF2000cc), and a braking distance from an initial speed of 100 km / h was determined on a wet asphalt road surface. The result is expressed as an index. The larger the number, the better the wet skid performance (wet grip performance). The index was calculated by the following formula.
Wet skid performance = (braking distance of reference comparative example) / (braking distance of each formulation) × 100

(Abrasion resistance)
Using a LAT tester (Laboratory Abrasion and Skid Tester), the volume loss of each vulcanized rubber composition was measured under the conditions of a load of 50 N, a speed of 20 km / h, and a slip angle of 5 °. The numerical values (wear resistance index) in Tables 9 to 16 are relative values when the volume loss amount of the reference comparative example is 100. The larger the value, the better the wear resistance.

As shown in Tables 9 to 16, Examples in which at least one of the conjugated diene polymers (A) to (H), silica, and conductive carbon black were blended in a predetermined amount are rubber compositions of comparative examples. Compared to the above, fuel efficiency, wet grip performance and wear resistance were synergistically improved, and these performances were obtained at a high level and well-balanced.

Claims (43)

Contains a rubber component, silica, and conductive carbon black,
In 100% by mass of the rubber component, a monomer unit based on a conjugated diene, a monomer unit based on a compound represented by the following formula (11), and a monomer based on a compound represented by the following formula (12) The content of the conjugated diene polymer (A) having a body unit is 5% by mass or more,
The rubber composition for treads whose content of the said silica is 5-150 mass parts and whose content of the said conductive carbon black is 3-30 mass parts with respect to 100 mass parts of said rubber components.

(Wherein R ¹¹¹ represents a hydrogen atom or a hydrocarbyl group, m ¹ is 0 or 1, R ¹¹² represents a hydrocarbylene group, and X ¹⁰¹ , X ¹⁰² and X ¹⁰³ are each independently substituted amino A hydrocarbyl group which may have a group or a substituent, and at least one of X ¹⁰¹ , X ¹⁰² and X ¹⁰³ is a substituted amino group.)

(In the formula, R ¹²¹ represents a hydrogen atom or a hydrocarbyl group, n ¹ is 0 or 1, R ¹²² represents a hydrocarbylene group, and A ¹⁰¹ represents a substituted amino group or a nitrogen-containing heterocyclic group. .) The rubber composition for a tread according to claim ¹ , wherein R ^{111 in the} formula (11) is a hydrogen atom, and m ¹ is 0. R ^{121 in the} formula (12) is a hydrogen atom, n ¹ is 1, R ¹²² is a group represented by the following formula (12-Y), and A ¹⁰¹ is a substituted amino group. Or the rubber composition for treads of 2.

(Wherein, ^{r 1} represents an integer of 0 to 5, when ^{r 1} is an integer of from 5 to _{1, (CH 2) r1} is a substituent on the benzene _{ring, (CH 2) r1} is ^{A 101} And when r ¹ is 0, (CH ₂ ) _r1 represents a bond between the benzene ring and A ^101. ) The vinyl bond content of the conjugated diene polymer (A) is 20 mol% or more and 70 mol% or less, where the content of the constituent unit based on the conjugated diene is 100 mol%. Rubber composition for treads. Contains a rubber component, silica, and conductive carbon black,
In 100% by mass of the rubber component, a monomer unit based on a conjugated diene, a monomer unit based on a compound represented by the following formula (21), and a single amount based on a compound represented by the following formula (22) The content of the conjugated diene polymer (B) obtained by reacting the alkoxysilane compound with one end of the copolymer having a body unit is 5% by mass or more,
The rubber composition for treads whose content of the said silica is 5-150 mass parts and whose content of the said conductive carbon black is 3-30 mass parts with respect to 100 mass parts of said rubber components.

(In the formula, V ²⁰¹ represents a hydrocarbyl group having a polymerizable carbon-carbon double bond, and S ²⁰¹ represents a substituted silyl group.)

(In the formula, V ²⁰² represents a hydrocarbyl group having a polymerizable carbon-carbon double bond, and A ²⁰² represents a substituted amino group or a nitrogen-containing heterocyclic group.) The rubber composition for a tread according to claim 5, wherein the alkoxysilane compound is a compound represented by the following formula (23).

(In the formula, p ² represents an integer of 1 to 10, R ²³¹ , R ²³² and R ²³³ each independently represents an alkyl group or an alkoxy group, and at least one of R ²³¹ , R ²³² and R ²³³ is an alkoxy group. And A ²⁰³ represents a substituted amino group.) The group represented by V ²⁰¹ in the formula (21) is a group represented by the following formula (21-V1), and the group represented by S ²⁰¹ in the formula (21) is represented by the following formula (21-S The rubber composition for a tread according to claim 5 or 6, wherein the rubber composition is a group represented by

(Wherein R ²¹¹ represents a hydrogen atom or a hydrocarbyl group, n ² is 0 or 1, and R ²¹² represents a hydrocarbylene group.)

(Wherein, X ²⁰¹ , X ²⁰² and X ²⁰³ each independently represent a substituted amino group or a hydrocarbyl group which may have a substituent, wherein at least one of X ²⁰¹ , X ²⁰² and X ²⁰³ is A substituted amino group.) The rubber composition for a tread according to claim 7, wherein R ^{211 in the} formula (21-V1) is a hydrogen atom, and n ² is 0. Formula (22) a group represented by ^{V 202} in the tread rubber composition according to any one of claims 5-8 is a group represented by the following formula (22-V1).

(Wherein R ²²¹ represents a hydrogen atom or a hydrocarbyl group, m ² represents 0 or 1, and R ²²² represents a hydrocarbylene group.) The rubber composition for a tread according to any one of claims 5 to 9, wherein the substituted amino group of A ^{202 in} the formula (22) is a group represented by the following formula (22-A).

(In the formula, each of R ²²⁵ and R ²²⁶ has a hydrocarbyl group, a trihydrocarbyl silyl group, or R ²²⁵ and R ²²⁶ bonded to each other, and has a nitrogen atom and / or an oxygen atom as a hetero atom. The hydrocarbylene group that may be substituted, or R ²²⁵ and R ²²⁶ are one group and represent a group bonded to the nitrogen atom with a double bond.) The vinyl bond content of the conjugated diene polymer (B) is 20 mol% or more and 70 mol% or less, where the content of the constituent unit based on the conjugated diene is 100 mol%. Rubber composition for treads. Contains a rubber component, silica, and conductive carbon black,
In 100% by mass of the rubber component, a monomer unit based on a conjugated diene, a monomer unit based on a compound represented by the following formula (31), and a monomer based on a compound represented by the following formula (32) The content of the conjugated diene polymer (C) having a body unit and at least one end of the copolymer modified with the following compound (G) is 5% by mass or more,
The rubber composition for treads whose content of the said silica is 5-150 mass parts and whose content of the said conductive carbon black is 3-30 mass parts with respect to 100 mass parts of said rubber components.

(In the formula, V ³⁰¹ represents a hydrocarbyl group having a polymerizable carbon-carbon double bond, and S ³⁰¹ represents a substituted silyl group.)

(In the formula, V ³⁰² represents a hydrocarbyl group having a polymerizable carbon-carbon double bond, and A ³⁰² represents a substituted amino group or a nitrogen-containing heterocyclic group.)
Compound (G): at least selected from the group consisting of a compound having an amino group and a carbonyl group which may have a substituent, and a compound having an amino group and a thiocarbonyl group which may have a substituent One compound. Formula (32) groups represented by ^{V 302} in the following formula (32-V1) according to claim 12 for tread rubber composition, wherein the group represented by.

(Wherein R ³²¹ represents a hydrogen atom or a hydrocarbyl group, m ³ represents 0 or 1, and R ³²² represents a hydrocarbylene group.) The rubber composition for a tread according to claim 12 or 13, wherein the substituted amino group of A ^{302 in} the formula (32) is a group represented by the following formula (32-A).

(In the formula, R ³²⁵ and R ³²⁶ each have a hydrocarbyl group, a trihydrocarbyl silyl group, or R ³²⁵ and R ³²⁶ bonded to each other and have a nitrogen atom and / or an oxygen atom as a hetero atom. The hydrocarbylene group which may be substituted, or R ³²⁵ and R ³²⁶ are one group and represent a group bonded to the nitrogen atom with a double bond.) The rubber composition for tread according to any one of claims 12 to 14, wherein the compound (G) is a compound represented by the following formula (33).

(In the formula, E represents an oxygen atom or a sulfur atom, and Z ³⁰¹ and Z ³⁰² have a substituted amino group, a hydrogen atom, a hydrocarbyl group which may have a substituent, or a substituent. represents also good hydrocarbyloxy ^group, or a group having at least one substituted amino group of ^{Z 301} and ^{Z 302, or} by bonding with ^{Z 301} and ^{Z 302,} a ring structure having a substituted amino group ^{Z 301} And represents a group formed by Z ³⁰² and a carbonyl carbon.) In the formula (33), E is an oxygen atom, Z ³⁰¹ is a group represented by the following formula (33-Z), and Z ³⁰² is a hydrocarbyl group or a group represented by the following formula (33-Z). The rubber composition for a tread according to claim 15.

(In the formula, p ³ is 0 or 1, and T ³⁰¹ is a hydrocarbylene group having 1 to 10 carbon atoms, a group represented by the following formula (33-Ta), or a following formula (33-Tb). A ³⁰³ represents a substituted amino group, and when Z ^{302 in} Formula (33) is a hydrocarbyl group, A ³⁰³ in Z ³⁰¹ and the hydrocarbyl group in Z ³⁰² may be bonded to each other. when ^{Z 302} of formula (33) is a group represented by the formula ^(33-Z), may be bonded to the ^{a 303} of the ^{a 303} and ^{Z 302} for ^{Z 301.)}

^{(Wherein, R 331} represents a hydrocarbylene group having 1 to 10 carbon ^{atoms, R 331} is bonded to ^{A 303.)}

(Wherein R ³³² represents a hydrocarbylene group having 1 to 10 carbon atoms, R ³³³ represents a hydrogen atom or a hydrocarbyl group having 1 to 10 carbon atoms, and R ³³² is bonded to A ^303. ) The group represented by V ³⁰¹ in the formula (31) is a group represented by the following formula (31-V1), and the group represented by S ³⁰¹ in the formula (31) is represented by the following formula (31-S The rubber composition for a tread according to any one of claims 12 to 16, wherein the rubber composition is a group represented by

(Wherein R ³¹¹ represents a hydrogen atom or a hydrocarbyl group, n ³ represents 0 or 1, and R ³¹² represents a hydrocarbylene group.)

( ^Wherein X ³⁰¹ , X ³⁰² and X ³⁰³ each independently represent a substituted amino group or a hydrocarbyl group which may have a substituent, wherein at least one of X ³⁰¹ , X ³⁰² and X ³⁰³ is A substituted amino group.) The rubber composition for a tread according to claim 17, wherein R ^{311 in the} formula (31-V1) is a hydrogen atom, and n ³ is 0. The vinyl bond content of the conjugated diene polymer (C) is 20 mol% or more and 70 mol% or less, where the content of the constituent unit based on the conjugated diene is 100 mol%. Rubber composition for treads. Contains a rubber component, silica, and conductive carbon black,
In 100% by mass of the rubber component, the content of the conjugated diene polymer (D) having a structural unit based on a conjugated diene and a structural unit based on the compound represented by the following formula (41) is 5% by mass or more,
The rubber composition for treads whose content of the said silica is 5-150 mass parts and whose content of the said conductive carbon black is 3-30 mass parts with respect to 100 mass parts of said rubber components.

(In the formula, m ⁴ represents an integer of 1 to 3, R ⁴⁰¹ represents a hydrocarbyl group having a polymerizable carbon-carbon double bond, R ⁴⁰² represents a hydrocarbylene group, and when there are a plurality of R ⁴⁰² , plural ^{R 402} may be the same or ^{different, a 401} represents a substituted amino ^{group, if a 401} there is a plurality, a plurality of ^{a 401} may be the same or ^{different, R 403} is a hydrocarbyl group, substituted hydrocarbyl represents a group or a substituted amino group, if R ⁴⁰³ is more, plural R ⁴⁰³ may be the same or different.) 21. The formula (41), wherein m ⁴ is 1, R ⁴⁰¹ is a group represented by the following formula (42), R ⁴⁰² is an alkylene group, and R ⁴⁰³ is an alkyl group. Tread rubber composition.

(In the formula, n ⁴ represents an integer of 0 to 2, and R ⁴²¹ , R ⁴²² and R ⁴²³ each independently represents a hydrogen atom or a hydrocarbyl group.) The rubber composition for a tread according to claim 21, wherein in the formula (42), R ⁴²¹ , R ⁴²² and R ⁴²³ are hydrogen atoms, and n ⁴ is 0. The molecular weight distribution represented by the ratio (Mw / Mn) of the weight average molecular weight (Mw) to the number average molecular weight (Mn) of the conjugated diene polymer (D) is 1 to 23. A rubber composition for tread according to claim 1. The vinyl bond content of the conjugated diene polymer (D) is 20 mol% or more and 70 mol% or less, with the content of the structural unit based on diene being 100 mol%. Tread rubber composition. Contains a rubber component, silica, and conductive carbon black,
In 100% by mass of the rubber component, the content of the conjugated diene polymer (E) having a structural unit based on a conjugated diene and a structural unit based on a compound represented by the following formula (51) is 5% by mass or more,
The rubber composition for treads whose content of the said silica is 5-150 mass parts and whose content of the said conductive carbon black is 3-30 mass parts with respect to 100 mass parts of said rubber components.

(In the formula, m ⁵ represents 1 or 2, n ⁵ represents 1 or 2, m ⁵ + n ⁵ represents 2 or 3, and R ⁵⁰¹ represents a hydrocarbyl group having a polymerizable carbon-carbon double bond. , ^{R 502} represents a hydrocarbyl ^{group, if R 502} is more, a plurality of ^{R 502} may be the same or ^{different, R 503} represents an aryl group which may have an oxygen-containing ^{substituent, R 503} When there are a plurality of R ^503s , the plurality of R ^503s may be the same or different, and R ⁵⁰⁴ represents an alkyl group or a substituted amino group.) In the formula (51), m ⁵ + n ⁵ is 3, R ⁵⁰¹ is a group represented by the following formula (52), R ⁵⁰² is a tertiary alkyl group, and R ⁵⁰³ has an alkyl group. The rubber composition for a tread according to claim 25, wherein the rubber composition is an optionally substituted phenyl group.

(In the formula, p ⁵ is 0 or 1, R ⁵⁰⁵ represents a hydrogen atom or a hydrocarbyl group, and T ⁵⁰¹ represents a hydrocarbylene group.) 27. The rubber composition for a tread according to claim 25 or 26, wherein in the formula (51), R ⁵⁰¹ is a vinyl group. The molecular weight distribution represented by the ratio (Mw / Mn) of the weight average molecular weight (Mw) and the number average molecular weight (Mn) of the conjugated diene polymer (E) is 1.0 to 1.5. The rubber composition for treads in any one of -27. The amount of vinyl bonds in the conjugated diene polymer (E) is 20 mol% or more and 70 mol% or less, with the content of the structural unit based on diene being 100 mol%. Tread rubber composition. Contains a rubber component, silica, and conductive carbon black,
Alkali obtained by polymerizing a conjugated diene monomer or a conjugated diene monomer and an aromatic vinyl monomer in an hydrocarbon solvent in the presence of a Lewis basic compound in 100% by mass of the rubber component. The content of the conjugated diene polymer (F) obtained by reacting the compound represented by the following formula (61) with respect to the active conjugated diene polymer having a metal terminal is 5% by mass or more,
The rubber composition for treads whose content of the said silica is 5-150 mass parts and whose content of the said conductive carbon black is 3-30 mass parts with respect to 100 mass parts of said rubber components.

(Wherein l ^{6 to} n ⁶ independently represent an integer of 1 to 8) The molecular weight distribution represented by the ratio (Mw / Mn) of the weight average molecular weight (Mw) and the number average molecular weight (Mn) of the conjugated diene polymer (F) is 1.0 to 1.5. The rubber composition for a tread as described. The rubber composition for a tread according to claim 30 or 31, wherein the vinyl bond content of the conjugated diene polymer (F) is 10 to 70 mol%, where the content of the conjugated diene unit is 100 mol%. Contains a rubber component, silica, and conductive carbon black,
In 100% by mass of the rubber component, a compound represented by the following formula (72) is attached to one end of a conjugated diene polymer having a structural unit based on a conjugated diene and a structural unit based on the compound represented by the following formula (71). The content of the conjugated diene polymer (G) obtained by the reaction is 5% by mass or more,
The rubber composition for treads whose content of the said silica is 5-150 mass parts and whose content of the said conductive carbon black is 3-30 mass parts with respect to 100 mass parts of said rubber components.

Wherein R ⁷¹¹ represents a hydrogen atom or a hydrocarbyl group having 1 to 5 carbon atoms, m ⁷ is 0 or 1, R ⁷¹² represents a hydrocarbylene group, and R ⁷¹³ and R ⁷¹⁴ are respectively Hydrocarbyl group, trihydrocarbyl silyl group, R ⁷¹³ and R ⁷¹⁴ are bonded to each other, and hydrocarbylene group optionally having nitrogen and / or oxygen atoms, or R ⁷¹³ and R ⁷¹⁴ are 1 group representing a group bonded to a nitrogen atom with a double bond.)

(In the formula, n ⁷ represents an integer of 1 to 10, R ⁷²¹ , R ⁷²² and R ⁷²³ each represents a hydrocarbyl group or a hydrocarbyloxy group, and at least one of R ⁷²¹ , R ⁷²² and R ⁷²³ is hydrocarbyloxy. Each of R ⁷²⁴ and R ⁷²⁵ is a hydrogen carbyl group which may have a hydrogen atom, a nitrogen atom and / or an oxygen atom, or R ⁷²⁴ and R ⁷²⁵ are bonded to each other to form a nitrogen atom and / Or a hydrocarbylene group which may have an oxygen atom, or R ⁷²⁴ and R ⁷²⁵ represent one group which represents a group bonded to a nitrogen atom with a double bond. The rubber composition for a tread according to claim 33, wherein, in the formula (71), R ⁷¹¹ is a hydrogen atom, m ⁷ is 1, and R ⁷¹² is a group represented by the following formula (73).

_{(Wherein, (CH 2) p7} is a substituent on the benzene ring, ^{p 7} represents an integer of 0 to 5, when ^{p 7} is an integer of 1 to _{5, (CH 2) p7} Formula ( 71) to the nitrogen atom.) The rubber composition for a tread according to claim 33 or 34, wherein, in the formula (72), R ⁷²¹ , R ⁷²² and R ⁷²³ are hydrocarbyloxy groups, and R ⁷²⁴ and R ⁷²⁵ are hydrocarbyl groups. The content of monomer units based on the compound represented by the formula (71) is 0.01 to 20% by mass, where the total amount of monomer units in the conjugated diene polymer (G) is 100% by mass. The rubber composition for tread according to any one of claims 33 to 35. The amount of vinyl bonds in the conjugated diene polymer (G) is from 20 mol% to 70 mol%, where the content of monomer units based on the conjugated diene is 100 mol%. The rubber composition for treads described in 1. Contains a rubber component, silica, and conductive carbon black,
In 100% by mass of the rubber component, a compound represented by the following formula (82) is attached to one end of a conjugated diene polymer having a structural unit based on a conjugated diene and a structural unit based on the compound represented by the following formula (81). The content of the monomer unit obtained by the reaction and based on the compound represented by the following formula (81) is 0.01 to 100% by weight based on the total amount of the monomer unit in the conjugated diene polymer. The content of the conjugated diene polymer (H) that is 20% by mass is 5% by mass or more,
The rubber composition for treads whose content of the said silica is 5-150 mass parts and whose content of the said conductive carbon black is 3-30 mass parts with respect to 100 mass parts of said rubber components.

(In the formula, R ⁸¹¹ represents a hydrogen atom or a hydrocarbyl group, m ⁸ is 0 or 1, R ⁸¹² represents a hydrocarbylene group, and T ⁸⁰¹ represents a nitrogen-containing heterocyclic group.)

(In the formula, n ⁸ represents an integer of 1 to 10, R ⁸²¹ , R ⁸²² and R ⁸²³ each represents a hydrocarbyl group or a hydrocarbyloxy group, and at least one of R ⁸²¹ , R ⁸²² and R ⁸²³ is hydrocarbyloxy. Each of R ⁸²⁴ and R ⁸²⁵ is a hydrocarbyl group optionally having a hydrogen atom, a nitrogen atom and / or an oxygen atom, or a combination of R ⁸²⁴ and R ⁸²⁵ to form a nitrogen atom and / Or a hydrocarbylene group which may have an oxygen atom, or R ⁸²⁴ and R ⁸²⁵ are one group and represent a group bonded to a nitrogen atom by a double bond.) The rubber composition for a tread according to claim 38, wherein in the formula (82), R ⁸²¹ , R ⁸²² and R ⁸²³ are hydrocarbyloxy groups, and R ⁸²⁴ and R ⁸²⁵ are hydrocarbyl groups. 40. The rubber composition for a tread according to claim 38 or 39, wherein in the formula (81), R ⁸¹¹ is a hydrogen atom, and T ⁸⁰¹ is a pyridyl group. The vinyl bond content of the conjugated diene polymer (H) is 20 mol% or more and 70 mol% or less, where the content of monomer units based on the conjugated diene is 100 mol%. The rubber composition for treads described in 1. The conductive carbon black, the nitrogen adsorption specific surface area of 40 to 80 m ² / g, a tread rubber composition according to any one of claims 1-41 dibutyl phthalate absorption is 110~230cm ³ / 100g. The pneumatic tire produced using the rubber composition in any one of Claims 1-42.