JP2010270051A - Organosilicon compound, and rubber composition, tire, primer composition, coating composition and adhesive, each using the same - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a new compound which can largely reduce the hysteresis loss of a rubber composition and can greatly improve the abrasion resistance, to provide a rubber composition containing the compound, to provide a tire using the rubber composition, and to provide a primer composition, a coating composition, and an adhesive composition, containing the compound. <P>SOLUTION: The organosilicon compound includes a silicon atom bound to at least one substituent reacting with silica, and a sulfur atom bound to a substituent containing an electron-attractive group, in the molecule. The substituent reacting with silica may be a group containing an oxygen atom directly bound to the silicon atom. <P>COPYRIGHT: (C)2011,JPO&INPIT

Description

  The present invention relates to an organosilicon compound, a rubber composition containing the organosilicon compound, a tire using the rubber composition, and a primer composition, a coating composition and an adhesive composition containing the organosilicon compound, The present invention relates to an organosilicon compound capable of reducing hysteresis loss of a rubber composition and improving wear resistance.

  Recently, from the viewpoint of vehicle safety, it is required to improve the safety of tires on wet road surfaces. In addition, from the viewpoint of reducing carbon dioxide emissions due to increased interest in environmental issues, it is also required to further reduce fuel consumption of vehicles.

  In response to these demands, conventionally, as a technique for achieving both improvement in performance on a wet road surface of a tire and reduction in rolling resistance, a technique of using an inorganic filler such as silica as a filler of a rubber composition used for a tire tread is known. It is known to be effective. However, the rubber composition containing an inorganic filler such as silica reduces the rolling resistance of the tire, improves the braking performance on the wet road surface, and improves the handling stability, but has a high unvulcanized viscosity and multistage kneading. Therefore, there is a problem in workability. Therefore, in a rubber composition containing an inorganic filler such as silica, the breaking strength and wear resistance are greatly reduced, and problems such as vulcanization delay and poor filler dispersion occur. Therefore, when an inorganic filler such as silica is blended with the rubber composition for tread, the unvulcanized viscosity of the rubber composition is reduced, the modulus and wear resistance are ensured, and the hysteresis loss is further reduced. It is essential to add a silane coupling agent.

U.S. Pat. No. 3,842,111 US Pat. No. 3,873,489

  However, since the silane coupling agent is expensive, the blending cost increases due to the blending of the silane coupling agent. Also, the addition of a dispersion improver decreases the unvulcanized viscosity of the rubber composition and improves workability, but also decreases the wear resistance. Furthermore, when the dispersion improver is a highly ionic compound, a decrease in workability such as roll adhesion is also observed. Furthermore, as a result of investigation by the present inventor, even when an inorganic filler such as silica is blended as a filler, even when a conventional silane coupling agent is added, the hysteresis loss of the rubber composition is reduced and the wear resistance is reduced. It was found that the level of improvement could not be sufficiently satisfied and there was still room for improvement.

  Accordingly, an object of the present invention is to solve the above-mentioned problems of the prior art, and to provide a novel compound capable of greatly reducing the hysteresis loss of the rubber composition and greatly improving the wear resistance. . Another object of the present invention is to provide a rubber composition containing such a compound, a tire using the rubber composition, a primer composition containing the compound, a coating composition, and an adhesive composition. .

  As a result of intensive studies to achieve the above object, the present inventors have found that an organosilicon compound containing a silicon atom and a sulfur atom bonded to a specific group has a reaction rate with an inorganic filler such as silica. Because it is high, blending the organosilicon compound with a rubber component together with an inorganic filler improves the efficiency of the coupling reaction, greatly reducing the hysteresis loss of the rubber composition and greatly improving the wear resistance. As a result, the present invention has been completed.

The organosilicon compound of the present invention is
The molecule has a silicon atom to which at least one substituent that reacts with silica is bonded and a sulfur atom to which a substituent including an electron withdrawing group is bonded.
The substituent that reacts with silica may be a group containing an oxygen atom directly bonded to a silicon atom.
The organosilicon compound has the following general formula (I):

［式（Ｉ）中、Ｒ¹、Ｒ²及びＲ³は、少なくとも一つが下記一般式（II）又は式（III）：

[In the formula (I), at least one of R ¹ , R ² and R ³ is the following general formula (II) or formula (III):

(In Formula (II) and Formula (III), M is —O— or —CH ₂ —, X and Y are each independently —O—, —NR ⁸ — or —CH ₂ —, and R ⁶ is -OR ^8, in -NR ⁸ R ⁹ or -R ^8, R ⁷ is ^{-NR 8 R 9, -NR 8 -NR} 8 R 9, in -N = NR ⁸ or H, provided that, R ⁸ is -C _n H _{2n + 1} , R ⁹ is —C _q H _{2q + 1} , and each of l, m, n and q is independently 0 to 20).
Others -M-C _l H _{2l + 1} or _{-M-C l H 2l-1} ( where, M and l have the same meanings as mentioned above), or _{- (M-C l H 2l} ) y C s H _{2s + 1} (M and l are as defined above, y and s are each independently 1 to 20), provided that one or more of R ¹ , R ² and R ³ is M − O-
R ⁴ represents the following general formula (IV) or formula (V):

(In formula (IV) and formula (V), M, X, Y, R ⁶ , l and m are as defined above, and R ¹⁰ is —NR ⁸ —, —NR ⁸ —NR ⁸ — or —N═. N-, wherein R ⁸ is as defined above) or -M-C ₁ H _2l — (wherein M and l are as defined above),
A ¹ represents the following general formula (VI) or formula (VII):

(In the formula (VI) and formula (VII), R ⁵ is the general formula (II) or Formula (III) or -C _l H _2l -R ¹¹ (wherein, R ¹¹ is -NR ⁸ R ^9, -NR ⁸ —NR ⁸ R ⁹ , —N═NR ⁸ , —M—C _m H _{2m + 1} or —M—C _m H _2m−1 , or a hydrocarbon group having an aromatic ring having 6 to 20 carbon atoms. Wherein R ⁸ , R ⁹ , M, l and m are as defined above), and R ¹⁶ is _a saturated or unsaturated group represented by —C _a H _{2a + 1} or —C _a H _2a-1. A saturated hydrocarbon group, and R ¹⁷ is a saturated or unsaturated hydrocarbon group represented by —C _b C _{2b + 1} or —C _b H _2b-1 (provided that a and b are each independently 0-20),
In formula (VII), Z and Q are each independently O, S or NR ⁵ , where R ⁵ is as defined above.

  The organosilicon compound is represented by the following general formula (VIII):

[In the formula (VIII), W is —NR ⁸ —, —O— or —CR ⁸ R ¹⁵ — (wherein R ¹⁵ is —R ⁹ or —C _m H _2m —R ⁷ , provided that R ⁷ Is —NR ⁸ R ⁹ , —NR ⁸ —NR ⁸ R ⁹ , —N═NR ⁸ or H, R ⁸ is —C _n H _{2n + 1} , R ⁹ is —C _q H _{2q + 1} , m, n and q are each independently 0 to 20),
R ¹² and R ¹³ are each independently represented by —M—C ₁ H _{2 1} — (wherein M is —O— or —CH ₂ —, and 1 is 0 to 20),
R ¹⁴ is _{-M-C l H 2l + 1} , -M-C l H 2l -R 7 ( wherein, M, R ⁷ and l have the same meanings as mentioned above), or _{- (M-C l H 2l} ) _y C _s H _{2s + 1} (M and l are as defined above, y and s are each independently 1 to 20), provided that one or more of R ¹² , R ¹³ and R ¹⁴ M is -O-
R ⁴ represents the following general formula (IV) or formula (V):

（式（IV）及び式（Ｖ）中、Ｍ、ｌ及びｍは上記と同義であり、Ｘ及びＹはそれぞれ独立して−Ｏ−、−ＮＲ⁸−又は−ＣＨ₂−で、Ｒ⁶は−ＯＲ⁸、−ＮＲ⁸Ｒ⁹又は−Ｒ⁸で、Ｒ¹⁰は−ＮＲ⁸−、−ＮＲ⁸−ＮＲ⁸−又は−Ｎ＝Ｎ−で、但し、Ｒ⁸及びＲ⁹は上記と同義である）或いは−Ｍ−Ｃ_lＨ_2l−（ここで、Ｍ及びｌは上記と同義である）で表され、
Ａ¹は下記一般式（VI）又は式（VII）：

(In formula (IV) and formula (V), M, l and m are as defined above, X and Y are each independently —O—, —NR ⁸ — or —CH ₂ —, and R ⁶ is in -OR ^8, -NR ⁸ R ⁹ or -R ^8, R ¹⁰ is ^{-NR 8 -, - NR 8 -NR} 8 - or -N = N-a, provided that, R ⁸ and R ⁹ is as defined above Or -M-C _l H _2l- (wherein M and l are as defined above),
A ¹ represents the following general formula (VI) or formula (VII):

(In the formula (VI) and formula (VII), R ⁵ is the general formula (II) or Formula (III) or -C _l H _2l -R ¹¹ (wherein, R ¹¹ is -NR ⁸ R ^9, -NR ⁸ —NR ⁸ R ⁹ , —N═NR ⁸ , —M—C _m H _{2m + 1} or —M—C _m H _2m−1 , or a hydrocarbon group having an aromatic ring having 6 to 20 carbon atoms. Wherein R ⁸ , R ⁹ , M, l and m are as defined above), and R ¹⁶ is _a saturated or unsaturated group represented by —C _a H _{2a + 1} or —C _a H _2a-1. A saturated hydrocarbon group, and R ¹⁷ is a saturated or unsaturated hydrocarbon group represented by —C _b C _{2b + 1} or —C _b H _2b-1 (provided that a and b are each independently 0-20),
In the formula (VII), Z and Q are each independently O, S or NR ⁵ (wherein R ⁵ is as defined above).

Further, the M is preferably —O—.
In addition, at least one of R ¹ , R ² and R ³ is represented by —O— _Cl H _2l —R ⁷ (wherein R ⁷ and l are as defined above), and the others are —O—. C _l H _{2l + 1} (where l is as defined above),
R ⁴ is represented by —C ₁ H _2l — (wherein l is as defined above),
R ⁵ may be represented by —C ₁ H _2l —R ¹¹ (where R ¹¹ and l are as defined above).
Further, at least one of R ¹ , R ² and R ³ is represented by —O—C ₁ H _{2 1} —NR ⁸ R ⁹ (where R ⁸ , R ⁹ and 1 are as defined above),
R ⁵ may be —C _l H _{2l + 1} (where l is as defined above) or a hydrocarbon group having an aromatic ring having 6 to 20 carbon atoms.

The W is represented by —NR ⁸ — (wherein R ⁸ is as defined above),
R ¹² and R ¹³ are each independently represented by —O—C ₁ H _2l — (wherein l is as defined above),
R ¹⁴ is represented by —O—C ₁ H _2l —R ⁷ (wherein R ⁷ and l are as defined above),
R ⁴ is represented by —C ₁ H _2l — (wherein l is as defined above),
R ⁵ may be —C _l H _{2l + 1} (where l is as defined above) or a hydrocarbon group having an aromatic ring having 6 to 20 carbon atoms.

Further, the W is represented by —O— or —CR ⁸ R ⁹ — (wherein R ⁸ and R ⁹ are as defined above),
R ¹² and R ¹³ are each independently represented by —O—C ₁ H _2l — (wherein l is as defined above),
R ¹⁴ is represented by —O—C ₁ H _{2 1} —NR ⁸ R ⁹ (where R ⁸ , R ⁹ and l are as defined above),
R ⁴ is represented by —C ₁ H _2l — (wherein l is as defined above),
R ⁵ may be represented by —C ₁ H _{2l + 1} (where l is as defined above).

The rubber composition of the present invention is obtained by blending an inorganic filler (B) and the organosilicon compound (C) with a rubber component (A) made of natural rubber and / or a diene synthetic rubber. Features.
The rubber composition is formed by blending 5 to 140 parts by mass of the inorganic filler (B) with respect to 100 parts by mass of the rubber component (A) composed of the natural rubber and / or the diene synthetic rubber.
Further, the organosilicon compound (C) may be contained in an amount of 1 to 20% by mass based on the amount of the inorganic filler (B), and the inorganic filler (B) is silica or aluminum hydroxide. Desirably, the silica has a BET surface area of 40 to 350 m ² / g.
The tire of the present invention is characterized by using the above rubber composition.
Moreover, the primer composition, coating composition, and adhesive composition of the present invention are characterized by containing the organosilicon compound.

  According to the present invention, it has a specific molecular structure having a silicon atom to which at least one substituent that reacts with silica is bonded, and a sulfur atom to which a substituent containing an electron withdrawing group is bonded, It is possible to provide an organosilicon compound capable of greatly reducing the hysteresis loss of the rubber composition and capable of greatly improving the wear resistance. Moreover, the rubber composition containing this organosilicon compound, the tire using this rubber composition, a primer composition, a coating composition, and an adhesive composition can be provided.

Hereinafter, the present invention will be described in detail.
<Organic silicon compound>
The organosilicon compound of the present invention is
The molecule has a silicon atom to which at least one substituent that reacts with silica is bonded and a sulfur atom to which a substituent including an electron withdrawing group is bonded. The substituent that reacts with silica means a group exhibiting good reactivity capable of sufficiently causing a hydrolysis reaction or a condensation reaction at the interface with silica, and preferably a group containing an oxygen atom directly bonded to a silicon atom. And can greatly contribute to the improvement of the dispersibility of each component in the composition containing the organosilicon compound. In addition, the substituent containing an electron withdrawing group means a group that easily attracts electrons from the sulfur atom side that is a bonding atom, promotes the hydrolysis reaction on the side of the sulfur atom from which electrons have been separated, or other atoms. In addition, dispersibility can be improved by forming a chelate. That is, the organosilicon compound of the present invention has the greatest feature in that it has a sulfur atom to which a substituent containing an electron withdrawing group is bonded, and if the coupling agent can connect a polymer and silica, Since it can be said that the function can be sufficiently achieved, as described above, the substituent bonded to the silicon atom can be widely selected as long as it can bond to silica, and sufficiently exhibits the intended effect of the present invention. It functions effectively as a coupling agent to be obtained.

  More specifically, the organosilicon compound of the present invention is preferably a compound represented by the following general formula (I) and a compound represented by the following general formula (VIII). These organosilicon compounds may be used individually by 1 type, and may be used in combination of 2 or more type.

上記式（Ｉ）及び（VIII）中、Ａ¹は下記一般式（VI）または（VII）で表される。

In the above formulas (I) and (VIII), A ¹ is represented by the following general formula (VI) or (VII).

以下、上記式（Ｉ）及び（VIII）中のＡ¹が上記式（VI）で表される本発明の第一態様における有機ケイ素化合物、上記式（Ｉ）及び（VIII）中のＡ¹が上記式（VII）で表される本発明の第二態様における有機ケイ素化合物に分けて詳述する。

Hereinafter, the organosilicon compound in the first embodiment of the present invention in which A ¹ in the above formulas (I) and (VIII) is represented by the above formula (VI), and A ¹ in the above formulas (I) and (VIII) is The organic silicon compound in the second embodiment of the present invention represented by the above formula (VII) will be described in detail.

[Organic silicon compound in the first embodiment of the present invention (A ^{1 in} formula (I) and formula (VIII) is a compound of formula (VI))]
When A ^{1 in} Formula (I) and Formula (VIII) is represented by Formula (VI), in Formula (VI), the oxygen atom on the C═O group directly bonded to the sulfur atom in the organosilicon compound is In addition to having an electron withdrawing property, -OR ⁵ has a particularly strong electron withdrawing property, and therefore, it can sufficiently exert the effect of promoting the hydrolysis of the organosilicon compound. Hereinafter, the compound of the formula (I) and the compound of the formula (VIII) will be described.

<< Compound of Formula (I) >>
In the first embodiment of the present invention, the compound in which A ¹ in the formula (I) is the formula (VI) is represented by the following formula.

In the above formula (I), R ¹ , R ² and R ³ are all —M—C ₁ H _{2 1 + 1} (where M is —O— or —CH ₂ —, and 1 is 0 to 20 represented by a is), or at least one is represented by the general formula (II) or formula (III), others _{-M-C l H 2l + 1} ( wherein, M is -O- or -CH _2- , l is 0-20, or -M-C ₁ H _2l-1 (where M is -O- or -CH _2- , l is 0-20), or _{- (M-C l H 2l} ) y C s H 2s + 1 (M and l are as defined above, y and s are 1 to 20 independently) represented by. Provided that M is —O— in one or more of R ¹ , R ² and R ³ . In addition, since l is 0 to 20, -C _l H _{2l + 1} is hydrogen or an alkyl group having 1 to 20 carbon atoms. -C _l H _2l-1 is a hydrocarbon group containing hydrogen or an unsaturated bond (double bond) having 1 to 20 carbon atoms, since l is 0 to 20. Here, examples of the alkyl group having 1 to 20 carbon atoms include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, and a decyl group. It may be linear or branched. Examples of the hydrocarbon group containing an unsaturated bond having 1 to 20 carbon atoms include ethenyl group, propenyl group, butenyl group, pentenyl group, hexenyl group, heptenyl group, octenyl group and the like.

In the above formulas (II) and (III), M is —O— or —CH ₂ —, and 1 is 0-20. Moreover, in said formula (II), m is 0-20.

In the above formula (II), X and Y are each independently —O—, —NR ⁸ — or —CH ₂ —. Wherein, R ⁸ is -C _n H _{2n + 1, n} is 0 to 20. Note that -C _n H _{2n + 1} is hydrogen or an alkyl group having 1 to 20 carbon atoms because n is 0 to 20. Here, examples of the alkyl group having 1 to 20 carbon atoms include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, and a decyl group. It may be linear or branched.

In the above formula (II), R ⁶ is —OR ⁸ , —NR ⁸ R ⁹ or —R ⁸ . Wherein, R ⁸ is _{-C n H 2n + 1, R} 9 is -C _q H _{2q + 1,} n and q are 0 to 20 independently. Note that the -C _n H _{2n + 1,} are as described above, -C _q H _{2q + 1,} since q is 0 to 20, hydrogen or an alkyl group having 1 to 20 carbon atoms. Here, examples of the alkyl group having 1 to 20 carbon atoms include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, and a decyl group. It may be linear or branched.

In the above formula (III), R ⁷ is —NR ⁸ R ⁹ , —NR ⁸ —NR ⁸ R ⁹ , —N═NR ⁸ or H. Wherein, R ⁸ is _{-C n H 2n + 1, R} 9 is -C _q H _{2q + 1,} n and q are 0 to 20 independently. Note that the -C _n H _{2n + 1} and -C _q H _{2q + 1,} is as described above.

Further, in the above formula (I), R ⁴ is represented by the above general formula (IV) or (V), or —M—C ₁ H _2l —, and in particular, —C ₁ H _2l —. Where M is —O— or —CH ₂ — and l is 0-20. In addition, since l is 0 to 20, —C ₁ H _2l — is a single bond or an alkylene group having 1 to 20 carbon atoms. Here, as a C1-C20 alkylene group, a methylene group, ethylene group, trimethylene group, a propylene group, etc. are mentioned, This alkylene group may be linear or branched.

In the above formulas (IV) and (V), M is —O— or —CH ₂ —, and l and m are 0-20. In the formula (IV), X and Y are each independently —O—, —NR ⁸ — or —CH ₂ —, and R ⁶ is —OR ⁸ , —NR ⁸ R ⁹ or —R ⁸ . is there. R ⁸ and R ⁹ are as described above. Furthermore, in the above formula (V), R ¹⁰ is —NR ⁸ —, —NR ⁸ —NR ⁸ —, or —N═N—, where R ⁸ is —C _n H _{2n + 1} , the -C _n H _{2n + 1,} as described above.

R ⁵ in the above formula (VI) is represented by the above general formula (II) or (III), or —C ₁ H _2l —R ¹¹ , where R ¹¹ is —NR ⁸ R ⁹ , —NR ⁸ —NR ⁸ R ⁹ , —N═NR ⁸ , —M—C _m H _{2m + 1} or —M—C _m H _2m−1 , or carbonization having an aromatic ring having 6 to 20 carbon atoms. A hydrogen group, wherein R ⁸ , R ⁹ , M, l and m are as defined above. Incidentally, -C _l H _2l - is as described above for and -C _l H _{2l + 1,} also, -C _m H _{2m + 1,} since m is 0-20, hydrogen or carbon atoms 1 20 alkyl groups, and examples of the alkyl group having 1 to 20 carbon atoms include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, and decyl group. The alkyl group may be linear or branched. Examples of the hydrocarbon group having an aromatic ring having 6 to 20 carbon atoms include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a benzyl group, and a phenylethyl group. Among these, R ⁵ is preferably —C ₁ H _2l —R ¹¹ , particularly preferably —C ₁ H _{2l + 1} or a hydrocarbon group having an aromatic ring having 6 to 20 carbon atoms. .

R ¹⁶ in the above formula (VI) is a saturated or unsaturated hydrocarbon group represented by —C _a H _{2a + 1} or —C _a H _2a-1 , and R ¹⁷ is —C _b C _{2b + 1.} or -C a _b hydrocarbon group represented by saturated or unsaturated H _2b-1 (where, a and b are 0 to 20 independently). Since -C _a H _{2a + 1} is a is 0 to 20, a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, the methyl group as the alkyl group having 1 to 20 carbon atoms, an ethyl group, Examples thereof include a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, and a decyl group. The alkyl group may be linear or branched. -C _a H _2a-1 is also a hydrocarbon group containing hydrogen or an alkenyl group having 1 to 20 carbon atoms or an aromatic ring because a is 0 to 20. Here, examples of the alkenyl group having 1 to 20 carbon atoms include an ethenyl group, a propenyl group, a butenyl group, a hexenyl group, an octenyl group, and the like, and the alkenyl group may be linear or branched. Examples of the hydrocarbon group having an aromatic ring include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a benzyl group, and a phenylethyl group.

Further, since _-C b C _{2b + 1} is b is 0 to 20, a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, the methyl group as the alkyl group having 1 to 20 carbon atoms, an ethyl group, Examples thereof include a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, and a decyl group. The alkyl group may be linear or branched. Similarly, since b is 0 to 20, —C _b H _2b-1 is hydrogen or a hydrocarbon group containing an alkenyl group having 1 to 20 carbon atoms or an aromatic ring. Here, examples of the alkenyl group having 1 to 20 carbon atoms include an ethenyl group, a propenyl group, a butenyl group, a hexenyl group, an octenyl group, and the like, and the alkenyl group may be linear or branched. Examples of the hydrocarbon group having an aromatic ring include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a benzyl group, and a phenylethyl group.

In the compound of the above formula (I), M is preferably —O— (oxygen). In this case, M is -CH ₂ - are highly reactive with an inorganic filler such as silica as compared to compounds wherein.

In the compound of the above formula (I), at least one of R ¹ , R ² and R ³ is represented by —O—C ₁ H _{2 1} —R ⁷ , and the other is —O—C ₁ H _{2 1 +.} is preferably represented by _1, the R ⁴ is -C _l H _2l - is preferably represented by the above R ⁵ is preferably represented by -C _l H _2l -R ^11.

Furthermore, in the compound of the above formula (I), it is more preferable that at least one of R ¹ , R ² and R ³ is represented by —O—C ₁ H _{2 1} —NR ⁸ R ⁹ , and R ⁴ is — It is preferably represented by C ₁ H _2l- , and R ⁵ is more preferably -C ₁ H _{2l + 1} or a hydrocarbon group having an aromatic ring having 6 to 20 carbon atoms.

<< Compound of Formula (VIII) >>
In the first embodiment of the present invention, the compound in which A ¹ in the formula (VIII) is the formula (VI) is represented by the following formula.

In the above formula (VIII), W is represented by —NR ⁸ —, —O— or —CR ⁸ R ¹⁵ —, where R ¹⁵ is —R ⁹ or —C _m H _2m —R ⁷ . , provided that, R ⁷ is ^{-NR 8 R 9, -NR 8 -NR} 8 R 9, a -N = NR ⁸ or H, R ⁸ is _{-C n H 2n + 1, R} 9 is -C _q H _{In 2q + 1} , m, n, and q are each independently 0-20. Incidentally, -C _m H _2m -, since m is 0-20, a single bond or an alkylene group with 1 to 20 carbon atoms. Here, as a C1-C20 alkylene group, a methylene group, ethylene group, trimethylene group, a propylene group, etc. are mentioned, This alkylene group may be linear or branched. Moreover, -C _n H _{2n + 1} and -C _q H _{2q + 1,} since n and q are 0 to 20, hydrogen or an alkyl group having 1 to 20 carbon atoms. Here, examples of the alkyl group having 1 to 20 carbon atoms include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, and a decyl group. It may be linear or branched.

In the above formula (VIII), R ¹² and R ¹³ are each independently -M-C _l H _2l - is represented by, R ¹⁴ is -M-C _l H _{2l + 1} or -M-C _l H _2l represented by -R ^7, wherein, M is -O- or -CH ₂ -, R ⁷ is ^{-NR 8 R 9, -NR 8 -NR} 8 R 9, in -N = NR ⁸ or H R ⁸ is —C _n H _{2n + 1} , R ⁹ is —C _q H _{2q + 1} , and l, n, and q are each independently 0-20. However, in one or more of R ¹² , R ¹³ and R ¹⁴ , M is —O—. Note that -C _l H _2l -is a single bond or an alkylene group having 1 to 20 carbon atoms because l is 0 to 20, where the alkylene group having 1 to 20 carbon atoms includes a methylene group, Examples thereof include an ethylene group, a trimethylene group, and a propylene group. The alkylene group may be linear or branched. -C _l H _{2l + 1} is hydrogen or an alkyl group having 1 to 20 carbon atoms because l is 0 to 20, where the alkyl group having 1 to 20 carbon atoms is a methyl group, Examples thereof include an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, and a decyl group. The alkyl group may be linear or branched. Note that the -C _n H _{2n + 1} and -C _q H _{2q + 1,} is as described above.

In the above formula (VIII), R ⁴ is represented by the above general formula (IV) or formula (V), or —M—C ₁ H _2l —, and in particular, —C ₁ H _2l —. Wherein M is —O— or —CH ₂ — and l is 0-20. In addition, -C _l H _2l- is as described above.

In the above formulas (IV) and (V), M is —O— or —CH ₂ —, and l and m are 0-20. In the above formula (VI), X and Y are each independently —O—, —NR ⁸ — or —CH ₂ —, and R ⁶ is —OR ⁸ , —NR ⁸ R ⁹ or —R ⁸ . Yes, where R ⁸ is —C _n H _{2n + 1} and R ⁹ is —C _q H _{2q + 1} . Further, in the above formula (V), R ¹⁰ is —NR ⁸ —, —NR ⁸ —NR ⁸ —, or —N═N—, where R ⁸ is —C _n H _{2n + 1} . Note that the -C _n H _{2n + 1} and -C _q H _{2q + 1,} is as described above.

R ⁵ in the above formula (VI) is represented by the above general formula (II) or (III), or —C ₁ H _2l —R ¹¹ , where R ¹¹ is —NR ⁸ R ⁹ , —NR ⁸ —NR ⁸ R ⁹ , —N═NR ⁸ , —M—C _m H _{2m + 1} or —M—C _m H _2m−1 , or carbonization having an aromatic ring having 6 to 20 carbon atoms. A hydrogen group, wherein R ⁸ , R ⁹ , M, l and m are as defined above. In addition, -C _l H _2l -and -C _l H _{2l + 1} are as described above, and -C _m H _{2m + 1} is hydrogen or carbon number 1 because m is 0-20. Wherein the alkyl group having 1 to 20 carbon atoms includes a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, and a decyl group. And the alkyl group may be linear or branched. Examples of the hydrocarbon group having an aromatic ring having 6 to 20 carbon atoms include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a benzyl group, and a phenylethyl group. Among these, it is preferable R ⁵ is a hydrocarbon group having an aromatic ring -C _l H _{2l + 1} or 6 to 20 carbon atoms, particularly preferably -C _l H _{2l + 1.}
R ¹⁶ and R ¹⁷ in the above formula (VI) are as described above.

In the compound of the above formula (VIII), M is preferably —O— (oxygen). In this case, M is -CH ₂ - are highly reactive with an inorganic filler such as silica as compared to compounds wherein.

When W is represented by —NR ⁸ —, R ¹² and R ¹³ are preferably each independently represented by —O—C ₁ H _2l —, and R ¹⁴ is represented by —O—C ₁ H. is preferably represented by _2l -R ^7, said R ⁴ is -C _l H _2l - is preferably represented by the above R ⁵ is -C _l H _{2l + 1,} or an aromatic ring having 6 to 20 carbon atoms It is preferably a hydrocarbon group having

On the other hand, when the W is represented by —O— or —CR ⁸ R ⁹ —, the R ¹² and R ¹³ are preferably each independently represented by —O—C ₁ H _2l —, and the R ¹⁴ is It is preferably represented by —O—C ₁ H _2l —NR ⁸ R ⁹ , R ⁴ is preferably represented by —C ₁ H _2l —, and R ⁵ is represented by —C ₁ H _{2l + 1.} It is preferable.

<< Specific Example of Organosilicon Compound (A ¹ is a Compound of Formula (VI)) in the First Aspect of the Present Invention >>
Specifically, the organosilicon compound in the first aspect of the present invention is 3-methoxyethanoylthio-propyltriethoxysilane, 3-ethoxyethanoylthio-propyltriethoxysilane, 3-propoxyethanoylthio-propyltriethoxy. Silane, 3-butoxyethanoylthio-propyltriethoxysilane, 3-decanoxyethanoylthio-propyltriethoxysilane, 3-dodecanoxyethanoylthio-propyltriethoxysilane, 3-stearyloxyethanoylthio-propyltri Ethoxysilane, 3-methoxyethanoylthio-butyltriethoxysilane, 3-methoxyethanoylthio-pentyltriethoxysilane, 3-methoxyethanoylthio-octyltriethoxysilane, 3-methoxyethanoylthio-decyltriethoxysilane 3-methoxy Tanoylthio-dodecyltriethoxysilane, 3-methoxyethanoylthio-propyltrimethoxysilane, 3-methoxyethanoylthio-propyltributoxysilane, 3-methoxyethanoylthio-propyltridecanoxysilane, 3-methoxyethanoylthio 3-propyltridodecanoxysilane, 3-methoxyethanoylthio-propyltristearyloxysilane, 3-methoxyethanoylthio-propylmonomethyldiethoxysilane, 3-methoxyethanoylthio-propyldimethylmonoethoxysilane, 3-methoxy Ethanoylthio-propylmonoethyldiethoxysilane, 3-methoxyethanoylthio-propyldiethylmonoethoxysilane, 3-methoxyethanoylthio-propylmonodecyldiethoxysilane, 3-methoxyethanoylthio-propyldidecyl Mono silane,

  3-methoxyethanoylthio-propylmonomethoxydiethoxysilane, 3-methoxyethanoylthio-propyldimethoxymonoethoxysilane, 3-methoxyethanoylthio-propylmonobutoxydiethoxysilane, 3-methoxyethanoylthio-propyldi Butoxymonoethoxysilane, 3-methoxyethanoylthio-propylmonodecanoxydiethoxysilane, 3-methoxyethanoylthio-propyldidecanoxymonoethoxysilane, 3-methoxyethanoylthio-propylmono-2-ethylhexoxy Diethoxysilane, 3-methoxyethanoylthio-propyldi-2-ethylhexoxymonoethoxysilane, 3-methoxyethanoylthio-propyldi (2- (butoxyethoxy) ethoxy) monoethoxysilane, 3-methoxyethanoylthio-propyl 2- Butoxyethoxy) ethoxy diethoxy silane,

  3-phenoxyethanoylthio-propyltriethoxysilane, 3-crezzoxyethanoylthio-propyltriethoxysilane, 3-ethylphenoxyethanoylthio-propyltriethoxysilane, 3-butylphenoxyethanoylthio-propyltriethoxysilane, 3 -Phenoxyethanoylthio-butyltriethoxysilane, 3-phenoxyethanoylthio-pentyltriethoxysilane, 3-phenoxyethanoylthio-octyltriethoxysilane, 3-phenoxyethanoylthio-decyltriethoxysilane, 3-phenoxyethanoylthio-dodecyl Triethoxysilane, 3-phenoxyethanoylthio-propyltrimethoxysilane, 3-methoxyethanoylthio-propyltributoxysilane, 3-phenoxyethanoylthio-propyltridecanoxy Down, 3-diphenoxyethane data Neu thio - propyltrimethoxysilane dodecanoate silane, 3-diphenoxyethane data Neu thio - propyl tristearate Lilo silane, 3-diphenoxyethane data Neu thio - propyl tri (2- (butoxyethoxy) ethoxy) silane,

  3-phenoxyethanoylthio-propylmonomethyldiethoxysilane, 3-phenoxyethanoylthio-propyldimethylmonoethoxysilane, 3-phenoxyethanoylthio-propylmonoethyldiethoxysilane, 3-phenoxyethanoylthio-propyldiethylmonoethoxysilane, 3 -Phenoxyethanoylthio-propyl monodecyldiethoxysilane, 3-phenoxyethanoylthio-propyldidecylmonoethoxysilane, 3-phenoxyethanoylthio-propylmonomethoxydiethoxysilane, 3-phenoxyethanoylthio-propyldimethoxymonoethoxysilane, 3-phenoxyethanoylthio-propyl monobutoxydiethoxysilane, 3-phenoxyethanoylthio-propyldibutoxymonoethoxysilane, 3-phenoxyethanoylchi -Propyl monodecanoxydiethoxysilane, 3-phenoxyethanoylthio-propyldidecanoxymonoethoxysilane, 3-phenoxyethanoylthio-propylmono-2-ethylhexoxydiethoxysilane, 3-phenoxyethanoylthio-propyldi-2 -Ethylhexoxymonoethoxysilane, 3-phenoxyethanoylthio-propyldi (2- (butoxyethoxy) ethoxy) monoethoxysilane, 3-phenoxyethanoylthio-propyl2- (butoxyethoxy) ethoxydiethoxysilane,

  3-methoxyethanoylthio-propyl (ethoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-ethoxyethanoylthio-propyl (ethoxy) 1,3-dioxa-6-methylaza-2- Silacyclooctane, 3-propoxyethanoylthio-propyl (ethoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-butoxyethanoylthio-propyl (ethoxy) 1,3-dioxa-6- Methylaza-2-silacyclooctane, 3-pentoxyethanoylthio-propyl (ethoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-decanoxyethanoylthio-propyl (ethoxy) 1, 3-Dioxa-6-methylaza-2-silacyclooctane, 3-dodecanoxyethanoylthio-propyl (ethoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3- Enoxyethanoylthio-propyl (ethoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-crezzoxyethanoylthio-propyl (ethoxy) 1,3-dioxa-6-methylaza-2 -Silacyclooctane, 3-butylphenoxyethanoylthio-propyl (ethoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-methoxyethanoylthio-propyl (methyl) 1,3-dioxa-6 -Methylaza-2-silacyclooctane, 3-methoxyethanoylthio-propyl (ethyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-methoxyethanoylthio-propyl (butyl) 1,3 -Dioxa-6-methylaza-2-silacyclooctane, 3-methoxyethanoylthio-propyl (octyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-methoxy Ethanoylthio-propyl (decyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-methoxyethanoylthio-propyl (dodecyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3 -Methoxyethanoylthio-propyl (stearyl) 1,3-dioxa-6-methylaza-2-silacyclooctane,

  3-phenoxyethanoylthio-propyl (methyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-phenoxyethanoylthio-propyl (ethyl) 1,3-dioxa-6-methylaza-2-silacyclo Octane, 3-phenoxyethanoylthio-propyl (butyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-phenoxyethanoylthio-propyl (octyl) 1,3-dioxa-6-methylaza-2- Silacyclooctane, 3-phenoxyethanoylthio-propyl (decyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-phenoxyethanoylthio-propyl (dodecyl) 1,3-dioxa-6-methylaza- 2-Silacyclooctane, 3-phenoxyethanoylthio-propyl (stearyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-me Xylethanoylthio-propyl (methoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-methoxyethanoylthio-propyl (butoxy) 1,3-dioxa-6-methylaza-2-silacyclo Octane, 3-methoxyethanoylthio-propyl (octanoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-methoxyethanoylthio-propyl (decanoxy) 1,3-dioxa-6-methylaza- 2-Silacyclooctane, 3-methoxyethanoylthio-propyl (dodecanoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-methoxyethanoylthio-propyl (stearyloxy) 1,3-dioxa- 6-Methylaza-2-silacyclooctane, 3-methoxyethanoylthio-propyl (2- (butoxyethoxy) ethoxy) 1,3-dioxa-6-methylaza- - silacyclooctane,

  3-Phenoxyethanoylthio-propyl (methoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-phenoxyethanoylthio-propyl (butanoxy) 1,3-dioxa-6-methylaza-2-silacyclo Octane, 3-phenoxyethanoylthio-propyl (octanoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-phenoxyethanoylthio-propyl (decanoxy) 1,3-dioxa-6-methylaza-2- Silacyclooctane, 3-phenoxyethanoylthio-propyl (dodecanoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-phenoxyethanoylthio-propyl (stearyloxy) 1,3-dioxa-6-methylaza- 2-silacyclooctane,

  3-Phenoxyethanoylthio-propyl (2- (butoxyethoxy) ethoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-methoxyethanoylthio-propyl (methyl) 1,3-dioxa-6 -Ethylaza-2-silacyclooctane, 3-methoxyethanoylthio-propyl (methyl) 1,3-dioxa-6-propylaza-2-silacyclooctane, 3-methoxyethanoylthio-propyl (methyl) 1,3 -Dioxa-6-butylaza-2-silacyclooctane, 3-methoxyethanoylthio-propyl (methyl) 1,3-dioxa-6-hexylaza-2-silacyclooctane, 3-methoxyethanoylthio-propyl (methyl) ) 1,3-Dioxa-6-octylaza-2-silacyclooctane, 3-methoxyethanoylthio-propyl (methyl) 1,3-dioxa-6-decylaza-2-silacycloo Tan, 3-methoxyethanoylthio-propyl (methyl) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-methoxyethanoylthio-propyl (methyl) 1,3-dioxa-6-stearylaza -2 -silacyclooctane,

  3-Phenoxyethanoylthio-propyl (methyl) 1,3-dioxa-6-ethylaza-2-silacyclooctane, 3-phenoxyethanoylthio-propyl (methyl) 1,3-dioxa-6-propylaza-2-silacyclo Octane, 3-phenoxyethanoylthio-propyl (methyl) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-phenoxyethanoylthio-propyl (methyl) 1,3-dioxa-6-hexylaza-2- Silacyclooctane, 3-phenoxyethanoylthio-propyl (methyl) 1,3-dioxa-6-octylaza-2-silacyclooctane, 3-phenoxyethanoylthio-propyl (methyl) 1,3-dioxa-6-decylaza- 2-Silacyclooctane, 3-Phenoxyethanoylthio-propyl (methyl) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-F Roh carboxymethyl eth- Neu thio - propyl (methyl) 1,3-dioxa-6-Suteariruaza 2-silacyclooctane,

  3-phenoxyethanoylthio-propyl (didimethylaminoethoxy) methylsilane, 3-phenoxyethanoylthio-propyl (didiethylaminoethoxy) methylsilane, 3-phenoxyethanoylthio-propyl (didibutylaminoethoxy) methylsilane, 3-phenoxyethanoylthio- Propyl (didihexylaminoethoxy) methylsilane, 3-phenoxyethanoylthio-propyl (didi2-ethylhexylaminoethoxy) methylsilane, 3-phenoxyethanoylthio-propyl (didioctylaminoethoxy) methylsilane, 3-phenoxyethanoylthio-propyl (didi) (Decylaminoethoxy) methylsilane,

  3-methoxyethanoylthio-propyl (didimethylaminoethoxy) methylsilane, 3-methoxyethanoylthio-propyl (didiethylaminoethoxy) methylsilane, 3-methoxyethanoylthio-propyl (didibutylaminoethoxy) methylsilane, 3-methoxy Ethanoylthio-propyl (didihexylaminoethoxy) methylsilane, 3-methoxyethanoylthio-propyl (didi-2-ethylhexylaminoethoxy) methylsilane, 3-methoxyethanoylthio-propyl (didioctylaminoethoxy) methylsilane, 3-methoxy Ethanoylthio-propyl (dididecylaminoethoxy) methylsilane,

  3-Phenoxyethanoylthio-propyl (ethoxy) 1,3-dioxa-5-methylaza-2-silacyclooctane, 3-phenoxyethanoylthio-propyl (ethoxy) 1,3-dioxa-5-methylaza-2-silacyclono Nan, 3-phenoxyethanoylthio-propyl (ethoxy) 1,3-dioxa-6-methylaza-2-silacyclononane, 3-phenoxyethanoylthio-propyl (ethoxy) 1,3-dioxa-5-methylaza-2- Silacyclodecane, 3-phenoxyethanoylthio-propyl (ethoxy) 1,3-dioxa-6-methylaza-2-silacyclodecane, 3-phenoxyethanoylthio-propyl (ethoxy) 1,3-dioxa-7-methylaza- 2-silacyclodecane,

  3-Methoxyethanoylthio-pentyl (methoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-methoxyethanoylthio-pentyl (butoxy) 1,3-dioxa-6-methylaza-2- Silacyclooctane, 3-methoxyethanoylthio-pentyl (decanoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-methoxyethanoylthio-pentyl (dodecanoxy) 1,3-dioxa-6- Methylaza-2-silacyclooctane, 3-methoxyethanoylthio-pentyl (stearyloxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-methoxyethanoylthio-pentyl (2- (butoxyethoxy) Ethoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-methoxyethanoylthio-pentyl (ethyl) 1,3-dioxa-6-methylaza-2 -Silacyclooctane, 3-methoxyethanoylthio-pentyl (butyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-methoxyethanoylthio-pentyl (decyl) 1,3-dioxa-6 -Methylaza-2-silacyclooctane, 3-methoxyethanoylthio-pentyl (dodecyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-methoxyethanoylthio-pentyl (stearyl) 1,3 -Dioxa-6-methylaza-2-silacyclooctane,

  3-methoxyethanoylthio-octyl (methoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-methoxyethanoylthio-octyl (butoxy) 1,3-dioxa-6-methylaza-2- Silacyclooctane, 3-methoxyethanoylthio-octyl (decanoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-methoxyethanoylthio-octyl (dodecanoxy) 1,3-dioxa-6- Methylaza-2-silacyclooctane, 3-methoxyethanoylthio-octyl (stearyloxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-methoxyethanoylthio-octyl (2- (butoxyethoxy) Ethoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-methoxyethanoylthio-octyl (ethyl) 1,3-dioxa-6-methylaza-2 -Silacyclooctane, 3-methoxyethanoylthio-octyl (butyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-methoxyethanoylthio-octyl (decyl) 1,3-dioxa-6 -Methylaza-2-silacyclooctane, 3-methoxyethanoylthio-octyl (dodecyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-methoxyethanoylthio-octyl (stearyl) 1,3 -Dioxa-6-methylaza-2-silacyclooctane,

  3-Methoxyethanoylthio-decyl (methoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-methoxyethanoylthio-decyl (butoxy) 1,3-dioxa-6-methylaza-2- Silacyclooctane, 3-methoxyethanoylthio-decyl (decanoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-methoxyethanoylthio-decyl (dodecanoxy) 1,3-dioxa-6- Methylaza-2-silacyclooctane, 3-methoxyethanoylthio-decyl (stearyloxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-methoxyethanoylthio-decyl (2- (butoxyethoxy)) Ethoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-methoxyethanoylthio-decyl (ethyl) 1,3-dioxa-6-methylaza-2-silacyclooct Tan, 3-methoxyethanoylthio-decyl (butyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-methoxyethanoylthio-decyl (decyl) 1,3-dioxa-6-methylaza- 2-Silacyclooctane, 3-methoxyethanoylthio-decyl (dodecyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-methoxyethanoylthio-decyl (stearyl) 1,3-dioxa- 6-methylaza-2-silacyclooctane,

  3-Phenoxyethanoylthio-pentyl (methoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-phenoxyethanoylthio-pentyl (butoxy) 1,3-dioxa-6-methylaza-2-silacyclo Octane, 3-phenoxyethanoylthio-pentyl (decanoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-phenoxyethanoylthio-pentyl (dodecanoxy) 1,3-dioxa-6-methylaza-2- Silacyclooctane, 3-phenoxyethanoylthio-pentyl (stearyloxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-phenoxyethanoylthio-pentyl (2- (butoxyethoxy) ethoxy) 1,3- Dioxa-6-methylaza-2-silacyclooctane, 3-phenoxyethanoylthio-pentyl (ethyl) 1,3-dioxa- -Methylaza-2-silacyclooctane, 3-phenoxyethanoylthio-pentyl (butyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-phenoxyethanoylthio-pentyl (decyl) 1,3-dioxa -6-Methylaza-2-silacyclooctane, 3-phenoxyethanoylthio-pentyl (dodecyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-phenoxyethanoylthio-pentyl (stearyl) 1,3 -Dioxa-6-methylaza-2-silacyclooctane,

  3-Phenoxyethanoylthio-octyl (methoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-phenoxyethanoylthio-octyl (butoxy) 1,3-dioxa-6-methylaza-2-silacyclo Octane, 3-phenoxyethanoylthio-octyl (decanoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-phenoxyethanoylthio-octyl (dodecanoxy) 1,3-dioxa-6-methylaza-2- Silacyclooctane, 3-phenoxyethanoylthio-octyl (stearyloxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-phenoxyethanoylthio-octyl (2- (butoxyethoxy) ethoxy) 1,3- Dioxa-6-methylaza-2-silacyclooctane, 3-phenoxyethanoylthio-octyl (ethyl) 1,3-dioxa- -Methylaza-2-silacyclooctane, 3-phenoxyethanoylthio-octyl (butyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-phenoxyethanoylthio-octyl (decyl) 1,3-dioxa -6-methylaza-2-silacyclooctane, 3-phenoxyethanoylthio-octyl (dodecyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-phenoxyethanoylthio-octyl (stearyl) 1,3 -Dioxa-6-methylaza-2-silacyclooctane,

  3-Phenoxyethanoylthio-decyl (methoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-phenoxyethanoylthio-decyl (butoxy) 1,3-dioxa-6-methylaza-2-silacyclo Octane, 3-phenoxyethanoylthio-decyl (decanoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-phenoxyethanoylthio-decyl (dodecanoxy) 1,3-dioxa-6-methylaza-2- Silacyclooctane, 3-phenoxyethanoylthio-decyl (stearyloxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-phenoxyethanoylthio-decyl (2- (butoxyethoxy) ethoxy) 1,3- Dioxa-6-methylaza-2-silacyclooctane, 3-phenoxyethanoylthio-decyl (ethyl) 1,3-dioxa-6-methylaza-2- Silacyclooctane, 3-phenoxyethanoylthio-decyl (butyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-phenoxyethanoylthio-decyl (decyl) 1,3-dioxa-6-methylaza- 2-Silacyclooctane, 3-phenoxyethanoylthio-decyl (dodecyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-phenoxyethanoylthio-decyl (stearyl) 1,3-dioxa-6- Methylaza-2-silacyclooctane,

  3-Phenoxyethanoylthio-pentyl (methoxy) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-phenoxyethanoylthio-pentyl (butoxy) 1,3-dioxa-6-butylaza-2-silacyclo Octane, 3-phenoxyethanoylthio-pentyl (decanoxy) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-phenoxyethanoylthio-pentyl (dodecanoxy) 1,3-dioxa-6-butylaza-2- Silacyclooctane, 3-phenoxyethanoylthio-pentyl (stearyloxy) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-phenoxyethanoylthio-pentyl (2- (butoxyethoxy) ethoxy) 1,3- Dioxa-6-butylaza-2-silacyclooctane, 3-phenoxyethanoylthio-pentyl (ethyl) 1,3-dioxa- -Butylaza-2-silacyclooctane, 3-phenoxyethanoylthio-pentyl (butyl) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-phenoxyethanoylthio-pentyl (decyl) 1,3-dioxa -6-Butylaza-2-silacyclooctane, 3-phenoxyethanoylthio-pentyl (dodecyl) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-phenoxyethanoylthio-pentyl (stearyl) 1,3 -Dioxa-6-butylaza-2-silacyclooctane,

  3-Phenoxyethanoylthio-octyl (methoxy) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-phenoxyethanoylthio-octyl (butoxy) 1,3-dioxa-6-butylaza-2-silacyclo Octane, 3-phenoxyethanoylthio-octyl (decanoxy) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-phenoxyethanoylthio-octyl (dodecanoxy) 1,3-dioxa-6-butylaza-2- Silacyclooctane, 3-phenoxyethanoylthio-octyl (stearyloxy) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-phenoxyethanoylthio-octyl (2- (butoxyethoxy) ethoxy) 1,3- Dioxa-6-butylaza-2-silacyclooctane, 3-phenoxyethanoylthio-octyl (ethyl) 1,3-dioxa- -Butylaza-2-silacyclooctane, 3-phenoxyethanoylthio-octyl (butyl) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-phenoxyethanoylthio-octyl (decyl) 1,3-dioxa -6-Butylaza-2-silacyclooctane, 3-phenoxyethanoylthio-octyl (dodecyl) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-phenoxyethanoylthio-octyl (stearyl) 1,3 -Dioxa-6-butylaza-2-silacyclooctane,

  3-Phenoxyethanoylthio-decyl (methoxy) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-phenoxyethanoylthio-decyl (butoxy) 1,3-dioxa-6-butylaza-2-silacyclo Octane, 3-phenoxyethanoylthio-decyl (decanoxy) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-phenoxyethanoylthio-decyl (dodecanoxy) 1,3-dioxa-6-butylaza-2- Silacyclooctane, 3-phenoxyethanoylthio-decyl (stearyloxy) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-phenoxyethanoylthio-decyl (2- (butoxyethoxy) ethoxy) 1,3- Dioxa-6-butylaza-2-silacyclooctane, 3-phenoxyethanoylthio-decyl (ethyl) 1,3-dioxa-6-butylaza-2- Silacyclooctane, 3-phenoxyethanoylthio-decyl (butyl) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-phenoxyethanoylthio-decyl (decyl) 1,3-dioxa-6-butylaza- 2-Silacyclooctane, 3-phenoxyethanoylthio-decyl (dodecyl) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-phenoxyethanoylthio-decyl (stearyl) 1,3-dioxa-6- Butylaza-2-silacyclooctane,

  3-Phenoxyethanoylthio-pentyl (methoxy) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-phenoxyethanoylthio-pentyl (butoxy) 1,3-dioxa-6-dodecylaza-2-silacyclo Octane, 3-phenoxyethanoylthio-pentyl (decanoxy) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-phenoxyethanoylthio-pentyl (dodecanoxy) 1,3-dioxa-6-dodecylaza-2- Silacyclooctane, 3-phenoxyethanoylthio-pentyl (stearyloxy) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-phenoxyethanoylthio-pentyl (2- (butoxyethoxy) ethoxy) 1,3- Dioxa-6-dodecylaza-2-silacyclooctane, 3-phenoxyethanoylthio-pentyl (ethyl) 1, -Dioxa-6-dodecylaza-2-silacyclooctane, 3-phenoxyethanoylthio-pentyl (butyl) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-phenoxyethanoylthio-pentyl (decyl) 1 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-phenoxyethanoylthio-pentyl (dodecyl) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-phenoxyethanoylthio-pentyl (stearyl) ) 1,3-dioxa-6-dodecylaza-2-silacyclooctane,

  3-Phenoxyethanoylthio-octyl (methoxy) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-phenoxyethanoylthio-octyl (butoxy) 1,3-dioxa-6-dodecylaza-2-silacyclo Octane, 3-phenoxyethanoylthio-octyl (decanoxy) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-phenoxyethanoylthio-octyl (dodecanoxy) 1,3-dioxa-6-dodecylaza-2- Silacyclooctane, 3-phenoxyethanoylthio-octyl (stearyloxy) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-phenoxyethanoylthio-octyl (2- (butoxyethoxy) ethoxy) 1,3- Dioxa-6-dodecylaza-2-silacyclooctane, 3-phenoxyethanoylthio-octyl (ethyl) 1, -Dioxa-6-dodecylaza-2-silacyclooctane, 3-phenoxyethanoylthio-octyl (butyl) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-phenoxyethanoylthio-octyl (decyl) 1 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-phenoxyethanoylthio-octyl (dodecyl) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-phenoxyethanoylthio-octyl (stearyl) ) 1,3-dioxa-6-dodecylaza-2-silacyclooctane,

  3-phenoxyethanoylthio-decyl (methoxy) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-phenoxyethanoylthio-decyl (butoxy) 1,3-dioxa-6-dodecylaza-2-silacyclo Octane, 3-phenoxyethanoylthio-decyl (decanoxy) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-phenoxyethanoylthio-decyl (dodecanoxy) 1,3-dioxa-6 dodecylaza-2-sila Cyclooctane, 3-phenoxyethanoylthio-decyl (stearyloxy) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-phenoxyethanoylthio-decyl (2- (butoxyethoxy) ethoxy) 1,3-dioxa -6-dodecylaza-2-silacyclooctane, 3-phenoxyethanoylthio-decyl (ethyl) 1,3-dioxa-6-do Decylaza-2-silacyclooctane, 3-phenoxyethanoylthio-decyl (butyl) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-phenoxyethanoylthio-decyl (decyl) 1,3-dioxa- 6-dodecylaza-2-silacyclooctane, 3-phenoxyethanoylthio-decyl (dodecyl) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-phenoxyethanoylthio-decyl (stearyl) 1,3- Dioxa-6-dodecylaza-2-silacyclooctane,

  3-Butylphenoxyethanoylthio-propyl (methoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-butylphenoxyethanoylthio-propyl (butoxy) 1,3-dioxa-6-methylaza-2- Silacyclooctane, 3-butylphenoxyethanoylthio-propyl (decanoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-butylphenoxyethanoylthio-propyl (dodecanoxy) 1,3-dioxa-6- Methylaza-2-silacyclooctane, 3-butylphenoxyethanoylthio-propyl (stearyloxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-butylphenoxyethanoylthio-propyl (2- (butoxyethoxy) Ethoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane,

  3-Butylphenoxyethanoylthio-propyl (methyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-butylphenoxyethanoylthio-propyl (ethyl) 1,3-dioxa-6-methylaza-2- Silacyclooctane, 3-butylphenoxyethanoylthio-propyl (decyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-butylphenoxyethanoylthio-propyl (dodecyl) 1,3-dioxa-6- Methylaza-2-silacyclooctane, 3-butylphenoxyethanoylthio-propyl (stearyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-butylphenoxyethanoylthio-propyl (methoxy) 1,3- Dioxa-6-butylaza-2-silacyclooctane, 3-butylphenoxyethanoylthio-propyl (butoxy) 1,3-dioxy 6-Butylaza-2-silacyclooctane, 3-butylphenoxyethanoylthio-propyl (decanoxy) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-butylphenoxyethanoylthio-propyl (dodecanoxy) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-butylphenoxyethanoylthio-propyl (stearyloxy) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-butylphenoxyethanoylthio- Propyl (2- (butoxyethoxy) ethoxy) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-butylphenoxyethanoylthio-propyl (methyl) 1,3-dioxa-6-butylaza-2-sila Cyclooctane, 3-butylphenoxyethanoylthio-propyl (ethyl) 1,3-dioxa-6-butylaza-2-silacy Looctane, 3-butylphenoxyethanoylthio-propyl (decyl) 1,3-dioxa-6-butylaza-2-silacyclooctane,

  3-Butylphenoxyethanoylthio-propyl (dodecyl) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-butylphenoxyethanoylthio-propyl (stearyl) 1,3-dioxa-6-butylaza-2- Silacyclooctane, 3-butylphenoxyethanoylthio-propyl (methoxy) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-butylphenoxyethanoylthio-propyl (butoxy) 1,3-dioxa-6- Dodecylaza-2-silacyclooctane, 3-butylphenoxyethanoylthio-propyl (decanoxy) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-butylphenoxyethanoylthio-propyl (dodecanoxy) 1,3- Dioxa-6-dodecylaza-2-silacyclooctane, 3-butylphenoxyethanoylthio-propyl ( Stearyloxy) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-butylphenoxyethanoylthio-propyl (2- (butoxyethoxy) ethoxy) 1,3-dioxa-6-dodecylaza-2-silacyclooctane ,

  3-Butylphenoxyethanoylthio-propyl (methyl) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-butylphenoxyethanoylthio-propyl (ethyl) 1,3-dioxa-6-dodecylaza-2- Silacyclooctane, 3-butylphenoxyethanoylthio-propyl (decyl) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-butylphenoxyethanoylthio-propyl (dodecyl) 1,3-dioxa-6- Dodecylaza-2-silacyclooctane, 3-butylphenoxyethanoylthio-propyl (stearyl) 1,3-dioxa-6-dodecylaza-2-silacyclooctane.

[The organosilicon compound in the second embodiment of the present invention (A ¹ in the formula (I) and the formula (VIII) is a compound of the formula (VII))]
When A ^{1 in} formula (I) and formula (VIII) is represented by formula (VII), Z and Q in formula (VII) have electron withdrawing properties, so that at least a part of them is a coordination atom. Thus, a chelate can be formed with zinc oxide or the like, and the effect of improving the dispersibility of the organosilicon compound can be sufficiently exerted. Hereinafter, the compound of the formula (I) and the compound of the formula (VIII) will be described.

<< Compound of Formula (I) >>
In the first embodiment of the present invention, the compound in which A ¹ in formula (I) is formula (VII) is represented by the following formula.

In the above formula (I), R ¹ , R ² and R ³ are all —M—C ₁ H _{2 1 + 1} (where M is —O— or —CH ₂ —, and 1 is 0 to 20 represented by a is), or at least one is represented by the general formula (II) or formula (III), others _{-M-C l H 2l + 1} ( wherein, M is -O- or -CH _2- , l is 0-20, or -M-C ₁ H _2l-1 (where M is -O- or -CH _2- , l is 0-20), or _{- (M-C l H 2l} ) y C s H 2s + 1 (M and l are as defined above, y and s are 1 to 20 independently) represented by. Provided that M is —O— in one or more of R ¹ , R ² and R ³ . In addition, since l is 0 to 20, -C _l H _{2l + 1} is hydrogen or an alkyl group having 1 to 20 carbon atoms. -C _l H _2l-1 is a hydrocarbon group containing hydrogen or an unsaturated bond (double bond) having 1 to 20 carbon atoms, since l is 0 to 20. Here, examples of the alkyl group having 1 to 20 carbon atoms include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, and a decyl group. It may be linear or branched. Examples of the hydrocarbon group containing an unsaturated bond having 1 to 20 carbon atoms include ethenyl group, propenyl group, butenyl group, pentenyl group, hexenyl group, heptenyl group, octenyl group and the like.

In the above formulas (II) and (III), M is —O— or —CH ₂ —, and 1 is 0-20. Moreover, in said formula (II), m is 0-20.

In the above formula (II), X and Y are each independently —O—, —NR ⁸ — or —CH ₂ —. Wherein, R ⁸ is -C _n H _{2n + 1, n} is 0 to 20. Note that -C _n H _{2n + 1} is hydrogen or an alkyl group having 1 to 20 carbon atoms because n is 0 to 20. Here, examples of the alkyl group having 1 to 20 carbon atoms include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, and a decyl group. It may be linear or branched.

In the above formula (II), R ⁶ is —OR ⁸ , —NR ⁸ R ⁹ or —R ⁸ . Wherein, R ⁸ is _{-C n H 2n + 1, R} 9 is -C _q H _{2q + 1,} n and q are 0 to 20 independently. Note that the -C _n H _{2n + 1,} are as described above, -C _q H _{2q + 1,} since q is 0 to 20, hydrogen or an alkyl group having 1 to 20 carbon atoms. Here, examples of the alkyl group having 1 to 20 carbon atoms include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, and a decyl group. It may be linear or branched.

In the above formula (III), R ⁷ is —NR ⁸ R ⁹ , —NR ⁸ —NR ⁸ R ⁹ , —N═NR ⁸ or H. Wherein, R ⁸ is _{-C n H 2n + 1, R} 9 is -C _q H _{2q + 1,} n and q are 0 to 20 independently. Note that the -C _n H _{2n + 1} and -C _q H _{2q + 1,} is as described above.

Further, in the above formula (I), R ⁴ is represented by the above general formula (IV) or (V), or —M—C ₁ H _2l —, and in particular, —C ₁ H _2l —. Where M is —O— or —CH ₂ — and l is 0-20. In addition, since l is 0 to 20, —C ₁ H _2l — is a single bond or an alkylene group having 1 to 20 carbon atoms. Here, as a C1-C20 alkylene group, a methylene group, ethylene group, trimethylene group, a propylene group, etc. are mentioned, This alkylene group may be linear or branched.

In the above formulas (IV) and (V), M is —O— or —CH ₂ —, and l and m are 0-20. In the above formula (VI), X and Y are each independently —O—, —NR ⁸ — or —CH ₂ —, and R ⁶ is —OR ⁸ , —NR ⁸ R ⁹ or —R ⁸ . is there. R ⁸ and R ⁹ are as described above. Furthermore, in the above formula (V), R ¹⁰ is —NR ⁸ —, —NR ⁸ —NR ⁸ —, or —N═N—, where R ⁸ is —C _n H _{2n + 1} , the -C _n H _{2n + 1,} as described above.

R ⁵ in the above formula (VII) is represented by the above general formula (II) or (III), or —C ₁ H _2l —R ¹¹ , where R ¹¹ is —NR ⁸ R ⁹ , —NR ⁸ —NR ⁸ R ⁹ , —N═NR ⁸ , —M—C _m H _{2m + 1} or —M—C _m H _2m−1 , or carbonization having an aromatic ring having 6 to 20 carbon atoms. A hydrogen group, wherein R ⁸ , R ⁹ , M, l and m are as defined above. Incidentally, -C _l H _2l - is as described above for and -C _l H _{2l + 1,} also, -C _m H _{2m + 1,} since m is 0-20, hydrogen or carbon atoms 1 20 alkyl groups, and examples of the alkyl group having 1 to 20 carbon atoms include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, and decyl group. The alkyl group may be linear or branched. Examples of the hydrocarbon group having an aromatic ring having 6 to 20 carbon atoms include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a benzyl group, and a phenylethyl group. Among these, R ⁵ is preferably —C ₁ H _2l —R ¹¹ , particularly preferably —C ₁ H _{2l + 1} or a hydrocarbon group having an aromatic ring having 6 to 20 carbon atoms. .

Z and Q in the formula (VII) are each independently O, S or NR ⁵ , and it is particularly preferable that both Z and Q are O. R ⁵ is as described above.

In the compound of the above formula (I), M is preferably —O— (oxygen). In this case, M is -CH ₂ - are highly reactive with an inorganic filler such as silica as compared to compounds wherein.

In the compound of the above formula (I), at least one of R ¹ , R ² and R ³ is represented by —O—C ₁ H _{2 1} —R ⁷ , and the other is —O—C ₁ H _{2 1 +.} is preferably represented by _1, the R ⁴ is -C _l H _2l - is preferably represented by the above R ⁵ is preferably represented by -C _l H _2l -R ^11.

Furthermore, in the compound of the above formula (I), it is more preferable that at least one of R ¹ , R ² and R ³ is represented by —O—C ₁ H _{2 1} —NR ⁸ R ⁹ , and R ⁴ is — It is preferably represented by C ₁ H _2l- , and R ⁵ is more preferably -C ₁ H _{2l + 1} or a hydrocarbon group having an aromatic ring having 6 to 20 carbon atoms.

<< Compound of Formula (VIII) >>
In the first embodiment of the present invention, the compound in which A ¹ in formula (VIII) is formula (VII) is represented by the following formula.

In the above formula (VIII), W is represented by —NR ⁸ —, —O— or —CR ⁸ R ¹⁵ —, where R ¹⁵ is —R ⁹ or —C _m H _2m —R ⁷ . , provided that, R ⁷ is ^{-NR 8 R 9, -NR 8 -NR} 8 R 9, a -N = NR ⁸ or H, R ⁸ is _{-C n H 2n + 1, R} 9 is -C _q H _{In 2q + 1} , m, n, and q are each independently 0-20. Incidentally, -C _m H _2m -, since m is 0-20, a single bond or an alkylene group with 1 to 20 carbon atoms. Here, as a C1-C20 alkylene group, a methylene group, ethylene group, trimethylene group, a propylene group, etc. are mentioned, This alkylene group may be linear or branched. Moreover, -C _n H _{2n + 1} and -C _q H _{2q + 1,} since n and q are 0 to 20, hydrogen or an alkyl group having 1 to 20 carbon atoms. Here, examples of the alkyl group having 1 to 20 carbon atoms include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, and a decyl group. It may be linear or branched.

In the above formula (VIII), R ¹² and R ¹³ are each independently -M-C _l H _2l - is represented by, R ¹⁴ is -M-C _l H _{2l + 1} or -M-C _l H _2l represented by -R ^7, wherein, M is -O- or -CH ₂ -, R ⁷ is ^{-NR 8 R 9, -NR 8 -NR} 8 R 9, in -N = NR ⁸ or H R ⁸ is —C _n H _{2n + 1} , R ⁹ is —C _q H _{2q + 1} , and l, n, and q are each independently 0-20. However, in one or more of R ¹² , R ¹³ and R ¹⁴ , M is —O—. Note that -C _l H _2l -is a single bond or an alkylene group having 1 to 20 carbon atoms because l is 0 to 20, where the alkylene group having 1 to 20 carbon atoms includes a methylene group, Examples thereof include an ethylene group, a trimethylene group, and a propylene group. The alkylene group may be linear or branched. -C _l H _{2l + 1} is hydrogen or an alkyl group having 1 to 20 carbon atoms because l is 0 to 20, where the alkyl group having 1 to 20 carbon atoms is a methyl group, Examples thereof include an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, and a decyl group. The alkyl group may be linear or branched. Note that the -C _n H _{2n + 1} and -C _q H _{2q + 1,} is as described above.

In the above formula (VIII), R ⁴ is represented by the above general formula (IV) or formula (V), or —M—C ₁ H _2l —, and in particular, —C ₁ H _2l —. Wherein M is —O— or —CH ₂ — and l is 0-20. In addition, -C _l H _2l- is as described above.

In the above formulas (IV) and (V), M is —O— or —CH ₂ —, and l and m are 0-20. In the above formula (VI), X and Y are each independently —O—, —NR ⁸ — or —CH ₂ —, and R ⁶ is —OR ⁸ , —NR ⁸ R ⁹ or —R ⁸ . Yes, where R ⁸ is —C _n H _{2n + 1} and R ⁹ is —C _q H _{2q + 1} . Further, in the above formula (V), R ¹⁰ is —NR ⁸ —, —NR ⁸ —NR ⁸ —, or —N═N—, where R ⁸ is —C _n H _{2n + 1} . Note that the -C _n H _{2n + 1} and -C _q H _{2q + 1,} is as described above.

R ⁵ in the above formula (VII) is represented by the above general formula (II) or (III), or —C ₁ H _2l —R ¹¹ , where R ¹¹ is —NR ⁸ R ⁹ , —NR ⁸ —NR ⁸ R ⁹ , —N═NR ⁸ , —M—C _m H _{2m + 1} or —M—C _m H _2m−1 , or carbonization having an aromatic ring having 6 to 20 carbon atoms. A hydrogen group, wherein R ⁸ , R ⁹ , M, l and m are as defined above. In addition, -C _l H _2l -and -C _l H _{2l + 1} are as described above, and -C _m H _{2m + 1} is hydrogen or carbon number 1 because m is 0-20. Wherein the alkyl group having 1 to 20 carbon atoms includes a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, and a decyl group. And the alkyl group may be linear or branched. Examples of the hydrocarbon group having an aromatic ring having 6 to 20 carbon atoms include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a benzyl group, and a phenylethyl group. Among these, it is preferable R ⁵ is a hydrocarbon group having an aromatic ring -C _l H _{2l + 1} or 6 to 20 carbon atoms, particularly preferably -C _l H _{2l + 1.}

Z and Q in the formula (VII) are each independently O, S or NR ⁵ , and it is particularly preferable that both Z and Q are O. R ⁵ is as described above.

In the compound of the above formula (VIII), M is preferably —O— (oxygen). In this case, M is -CH ₂ - are highly reactive with an inorganic filler such as silica as compared to compounds wherein.

When W is represented by —NR ⁸ —, R ¹² and R ¹³ are preferably each independently represented by —O—C ₁ H _2l —, and R ¹⁴ is represented by —O—C ₁ H. is preferably represented by _2l -R ^7, said R ⁴ is -C _l H _2l - is preferably represented by the above R ⁵ is -C _l H _{2l + 1,} or an aromatic ring having 6 to 20 carbon atoms It is preferably a hydrocarbon group having

On the other hand, when the W is represented by —O— or —CR ⁸ R ⁹ —, the R ¹² and R ¹³ are preferably each independently represented by —O—C ₁ H _2l —, and the R ¹⁴ is It is preferably represented by —O—C ₁ H _2l —NR ⁸ R ⁹ , R ⁴ is preferably represented by —C ₁ H _2l —, and R ⁵ is represented by —C ₁ H _{2l + 1.} It is preferable.

<< Specific Example of Organosilicon Compound (A ¹ is a Compound of Formula (VII)) in the Second Aspect of the Present Invention >>
Specifically, as the organosilicon compound in the second embodiment of the present invention, 3-methyloxalylthio-propyltriethoxysilane, 3-ethylmethyloxalylthio-propyltriethoxysilane, 3-propyloxalylthio-propyltriethoxysilane, 3-pentyloxalylthio-propyltriethoxysilane, 3-octyloxalylthio-propyltriethoxysilane, 3-decyloxalylthio-propyltriethoxysilane, 3-dodecyloxalylthio-propyltriethoxysilane,

  3-methyloxalylthio-pentyltriethoxysilane, 3-ethylmethyloxalylthio-pentyltriethoxysilane, 3-propyloxalylthio-pentyltriethoxysilane, 3-pentyloxalylthio-pentyltriethoxysilane, 3-octyloxalylthio -Pentyltriethoxysilane, 3-decyloxalylthio-pentyltriethoxysilane, 3-dodecyloxalylthio-pentyltriethoxysilane,

  3-methyloxalylthio-decyltriethoxysilane, 3-ethylmethyloxalylthio-decyltriethoxysilane, 3-propyloxalylthio-decyltriethoxysilane, 3-decyloxalylthio-pentyltriethoxysilane, 3-octyloxalylthio -Decyltriethoxysilane, 3-decyloxalylthio-decyltriethoxysilane, 3-dodecyloxalylthio-decyltriethoxysilane,

  3-methyloxalylthio-propyltrimethoxysilane, 3-ethylmethyloxalylthio-propyltrimethoxysilane, 3-propyloxalylthio-propyltrimethoxysilane, 3-pentyloxalylthio-propyltrimethoxysilane, 3-octyloxalylthio -Propyltrimethoxysilane, 3-decyloxalylthio-propyltrimethoxysilane, 3-dodecyloxalylthio-propyltrimethoxysilane,

  3-methyloxalylthio-pentyltrimethoxysilane, 3-ethylmethyloxalylthio-pentyltrimethoxysilane, 3-propyloxalylthio-pentyltrimethoxysilane, 3-pentyloxalylthio-pentyltrimethoxysilane, 3-octyloxalylthio -Pentyltrimethoxysilane, 3-decyloxalylthio-pentyltrimethoxysilane, 3-dodecyloxalylthio-pentyltrimethoxysilane,

  3-methyloxalylthio-decyltrimethoxysilane, 3-ethylmethyloxalylthio-decyltrimethoxysilane, 3-propyloxalylthio-decyltrimethoxysilane, 3-decyloxalylthio-pentyltrimethoxysilane, 3-octyloxalylthio -Decyltrimethoxysilane, 3-decyloxalylthio-decyltrimethoxysilane, 3-dodecyloxalylthio-decyltrimethoxysilane,

  3-methyloxalylthio-propyltributoxysilane, 3-ethylmethyloxalylthio-propyltributoxysilane, 3-propyloxalylthio-propyltributoxysilane, 3-pentyloxalylthio-propyltributoxysilane, 3-octyloxalylthio -Propyltributoxysilane, 3-decyloxalylthio-propyltributoxysilane, 3-dodecyloxalylthio-propyltributoxysilane,

  3-methyloxalylthio-pentylriboxysilane, 3-ethylmethyloxalylthio-pentylriboxysilane, 3-propyloxalylthio-pentylriboxysilane, 3-pentyloxalylthio-pentylriboxysilane, 3-octyloxalylthio -Pentylriboxysilane, 3-decyloxalylthio-pentylriboxysilane, 3-dodecyloxalylthio-pentylriboxysilane,

  3-methyloxalylthio-decyltributoxysilane, 3-ethylmethyloxalylthio-decyltributoxysilane, 3-propyloxalylthio-decyltributoxysilane, 3-decyloxalylthio-pentylriboxysilane, 3-octyloxalylthio -Decyltributoxysilane, 3-decyloxalylthio-decyltributoxysilane, 3-dodecyloxalylthio-decyltributoxysilane,

  3-methyloxalylthio-propyltridecanoxysilane, 3-ethylmethyloxalylthio-propyltridecanoxysilane, 3-propyloxalylthio-propyltridecanoxysilane, 3-pentyloxalylthio-propyltridecanoxysilane, 3 -Octyloxalylthio-propyltridecanoxysilane, 3-decyloxalylthio-propyltridecanoxysilane, 3-dodecyloxalylthio-propyltridecanoxysilane,

  3-methyloxalylthio-pentyltridecanoxysilane, 3-ethylmethyloxalylthio-pentyltridecanoxysilane, 3-propyloxalylthio-pentyltridecanoxysilane, 3-pentyloxalylthio-pentyltridecanoxysilane, 3 -Octyloxalylthio-pentyltridecanoxysilane, 3-decyloxalylthio-pentyltridecanoxysilane, 3-dodecyloxalylthio-pentyltridecanoxysilane,

  3-methyloxalylthio-decyltridecanoxysilane, 3-ethylmethyloxalylthio-decyltridecanoxysilane, 3-propyloxalylthio-decyltridecanoxysilane, 3-decyloxalylthio-pentyltridecanoxysilane, 3 -Octyloxalylthio-decyltridecanoxysilane, 3-decyloxalylthio-decyltridecanoxysilane, 3-dodecyloxalylthio-decyltridecanoxysilane,

  3-methyloxalylthio-propylmethyldiethoxysilane, 3-ethylmethyloxalylthio-propylmethyldiethoxysilane, 3-propyloxalylthio-propylmethyldiethoxysilane, 3-pentyloxalylthio-propylmethyldiethoxysilane, 3 -Octyloxalylthio-propylmethyldiethoxysilane, 3-decyloxalylthio-propylmethyldiethoxysilane, 3-dodecyloxalylthio-propylmethyldiethoxysilane,

  3-methyloxalylthio-pentylmethyldiethoxysilane, 3-ethylmethyloxalylthio-pentylmethyldiethoxysilane, 3-propyloxalylthio-pentylmethyldiethoxysilane, 3-pentyloxalylthio-pentylmethyldiethoxysilane, 3 -Octyloxalylthio-pentylmethyldiethoxysilane, 3-decyloxalylthio-pentylmethyldiethoxysilane, 3-dodecyloxalylthio-pentylmethyldiethoxysilane,

  3-methyloxalylthio-decylmethyldiethoxysilane, 3-ethylmethyloxalylthio-decylmethyldiethoxysilane, 3-propyloxalylthio-decylmethyldiethoxysilane, 3-decyloxalylthio-pentylmethyldiethoxysilane, 3 -Octyloxalylthio-decylmethyldiethoxysilane, 3-decyloxalylthio-decylmethyldiethoxysilane, 3-dodecyloxalylthio-decylmethyldiethoxysilane,

  3-methyloxalylthio-propyldimethylethoxysilane, 3-ethylmethyloxalylthio-propyldimethylethoxysilane, 3-propyloxalylthio-propyldimethylethoxysilane, 3-pentyloxalylthio-propyldimethylethoxysilane, 3-octyloxalylthio -Propyldimethylethoxysilane, 3-decyloxalylthio-propyldimethylethoxysilane, 3-dodecyloxalylthio-propyldimethylethoxysilane,

  3-methyloxalylthio-propylmonodecanoxydiethoxysilane, 3-ethylmethyloxalylthio-propylmonodecanoxydiethoxysilane, 3-propyloxalylthio-propylmonodecanoxydiethoxysilane, 3-pentyloxalylthio-propyl Monodecanoxydiethoxysilane, 3-octyloxalylthio-propylmonodecanoxydiethoxysilane, 3-decyloxalylthio-propylmonodecanoxydiethoxysilane, 3-dodecyloxalylthio-propylmonodecanoxydiethoxysilane,

  3-methyloxalylthio-propyldidecanoxymonoethoxysilane, 3-ethylmethyloxalylthio-propyldidecanoxymonoethoxysilane, 3-propyloxalylthio-propyldidecanoxymonoethoxysilane, 3-pentyloxalylthio-propyl Didecanoxymonoethoxysilane, 3-octyloxalylthio-propyldidecanoxymonoethoxysilane, 3-decyloxalylthio-propyldidecanoxymonoethoxysilane, 3-dodecyloxalylthio-propyldidecanoxymonoethoxysilane,

  3-methyloxalylthio-propylmono (2-butoxyethoxy) ethoxydiethoxysilane, 3-ethylmethyloxalylthio-propylmono (2-butoxyethoxy) ethoxydiethoxysilane, 3-propyloxalylthio-propylmono (2- Butoxyethoxy) ethoxydiethoxysilane, 3-pentyloxalylthio-propylmono (2-butoxyethoxy) ethoxydiethoxysilane, 3-octyloxalylthio-propylmono (2-butoxyethoxy) ethoxydiethoxysilane, 3-decyloxalyl Thio-propylmono (2-butoxyethoxy) ethoxydiethoxysilane, 3-dodecyloxalylthio-propylmono (2-butoxyethoxy) ethoxydiethoxysilane,

  3-methyloxalylthio-propyldi (2-butoxyethoxy) ethoxymonoethoxysilane, 3-ethylmethyloxalylthio-propyldi (2-butoxyethoxy) ethoxymonoethoxysilane, 3-propyloxalylthio-propyldi (2-butoxyethoxy) Ethoxymonoethoxysilane, 3-pentyloxalylthio-propyldi (2-butoxyethoxy) ethoxymonoethoxysilane, 3-octyloxalylthio-propyldi (2-butoxyethoxy) ethoxymonoethoxysilane, 3-decyloxalylthio-propyldi (2 -Butoxyethoxy) ethoxymonoethoxysilane, 3-dodecyloxalylthio-propyldi (2-butoxyethoxy) ethoxymonoethoxysilane,

  3-methyloxalylthio-propyl (ethoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-ethyloxalylthio-propyl (ethoxy) 1,3-dioxa-6-methylaza-2-silacyclo Octane, 3-pentyloxalylthio-propyl (ethoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-octyloxalylthio-propyl (ethoxy) 1,3-dioxa-6-methylaza-2- Silacyclooctane, 3-decyloxalylthio-propyl (ethoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-dodecyloxalylthio-propyl (ethoxy) 1,3-dioxa-6-methylaza- 2-silacyclooctane,

  3-methyloxalylthio-propyl (methoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-ethyloxalylthio-propyl (methoxy) 1,3-dioxa-6-methylaza-2-silacyclo Octane, 3-pentyloxalylthio-propyl (methoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-octyloxalylthio-propyl (methoxy) 1,3-dioxa-6-methylaza-2- Silacyclooctane, 3-decyloxalylthio-propyl (methoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-dodecyloxalylthio-propyl (methoxy) 1,3-dioxa-6-methylaza- 2-silacyclooctane,

  3-Methyloxalylthio-propyl (butoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-ethyloxalylthio-propyl (butoxy) 1,3-dioxa-6-methylaza-2-silacyclo Octane, 3-pentyloxalylthio-propyl (butoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-octyloxalylthio-propyl (butoxy) 1,3-dioxa-6-methylaza-2- Silacyclooctane, 3-decyloxalylthio-propyl (butoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-dodecyloxalylthio-propyl (butoxy) 1,3-dioxa-6-methylaza- 2-silacyclooctane,

  3-Methyloxalylthio-propyl (decanoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-ethyloxalylthio-propyl (decanoxy) 1,3-dioxa-6-methylaza-2-silacyclo Octane, 3-pentyloxalylthio-propyl (decanoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-octyloxalylthio-propyl (decanoxy) 1,3-dioxa-6-methylaza-2- Silacyclooctane, 3-decyloxalylthio-propyl (decanoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-dodecyloxalylthio-propyl (decanoxy) 1,3-dioxa-6-methylaza- 2-silacyclooctane,

  3-Methyloxalylthio-propyl (2- (butoxyethoxy) ethoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-ethyloxalylthio-propyl (2- (butoxyethoxy) ethoxy) 1, 3-Dioxa-6-methylaza-2-silacyclooctane, 3-pentyloxalylthio-propyl (2- (butoxyethoxy) ethoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-octyloxalyl Thio-propyl (2- (butoxyethoxy) ethoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-decyloxalylthio-propyl (2- (butoxyethoxy) ethoxy) 1,3-dioxa- 6-Methylaza-2-silacyclooctane, 3-dodecyloxalylthio-propyl (2- (butoxyethoxy) ethoxy) 1,3-dioxa-6-me Tilaza-2-silacyclooctane,

  3-methyloxalylthio-propyl (methyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-ethyloxalylthio-propyl (methyl) 1,3-dioxa-6-methylaza-2-silacyclo Octane, 3-pentyloxalylthio-propyl (methyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-octyloxalylthio-propyl (methyl) 1,3-dioxa-6-methylaza-2- Silacyclooctane, 3-decyloxalylthio-propyl (methyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-dodecyloxalylthio-propyl (methyl) 1,3-dioxa-6-methylaza- 2-silacyclooctane,

  3-Methyloxalylthio-propyl (ethyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-ethyloxalylthio-propyl (ethyl) 1,3-dioxa-6-methylaza-2-silacyclo Octane, 3-pentyloxalylthio-propyl (ethyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-octyloxalylthio-propyl (ethyl) 1,3-dioxa-6-methylaza-2- Silacyclooctane, 3-decyloxalylthio-propyl (ethyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-dodecyloxalylthio-propyl (ethyl) 1,3-dioxa-6-methylaza- 2-silacyclooctane,

  3-Methyloxalylthio-propyl (decyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-ethyloxalylthio-propyl (decyl) 1,3-dioxa-6-methylaza-2-silacyclo Octane, 3-pentyloxalylthio-propyl (decyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-octyloxalylthio-propyl (decyl) 1,3-dioxa-6-methylaza-2- Silacyclooctane, 3-decyloxalylthio-propyl (decyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-dodecyloxalylthio-propyl (decyl) 1,3-dioxa-6-methylaza- 2-silacyclooctane,

  3-Methyloxalylthio-propyl (ethoxy) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-ethyloxalylthio-propyl (ethoxy) 1,3-dioxa-6-butylaza-2-silacyclo Octane, 3-pentyloxalylthio-propyl (ethoxy) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-octyloxalylthio-propyl (ethoxy) 1,3-dioxa-6-butylaza-2- Silacyclooctane, 3-decyloxalylthio-propyl (ethoxy) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-dodecyloxalylthio-propyl (ethoxy) 1,3-dioxa-6-butylaza- 2-silacyclooctane,

  3-Methyloxalylthio-propyl (methoxy) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-ethyloxalylthio-propyl (methoxy) 1,3-dioxa-6-butylaza-2-silacyclo Octane, 3-pentyloxalylthio-propyl (methoxy) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-octyloxalylthio-propyl (methoxy) 1,3-dioxa-6-butylaza-2- Silacyclooctane, 3-decyloxalylthio-propyl (methoxy) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-dodecyloxalylthio-propyl (methoxy) 1,3-dioxa-6-butylaza- 2-silacyclooctane,

  3-Methyloxalylthio-propyl (butoxy) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-ethyloxalylthio-propyl (butoxy) 1,3-dioxa-6-butylaza-2-silacyclo Octane, 3-pentyloxalylthio-propyl (butoxy) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-octyloxalylthio-propyl (butoxy) 1,3-dioxa-6-butylaza-2- Silacyclooctane, 3-decyloxalylthio-propyl (butoxy) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-dodecyloxalylthio-propyl (butoxy) 1,3-dioxa-6-butylaza- 2-silacyclooctane,

  3-methyloxalylthio-propyl (decanoxy) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-ethyloxalylthio-propyl (decanoxy) 1,3-dioxa-6-butylaza-2-silacyclo Octane, 3-pentyloxalylthio-propyl (decanoxy) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-octyloxalylthio-propyl (decanoxy) 1,3-dioxa-6-butylaza-2- Silacyclooctane, 3-decyloxalylthio-propyl (decanoxy) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-dodecyloxalylthio-propyl (decanoxy) 1,3-dioxa-6-butylaza- 2-silacyclooctane,

  3-methyloxalylthio-propyl (2- (butoxyethoxy) ethoxy) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-ethyloxalylthio-propyl (2- (butoxyethoxy) ethoxy) 1, 3-Dioxa-6-butylaza-2-silacyclooctane, 3-pentyloxalylthio-propyl (2- (butoxyethoxy) ethoxy) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-octyloxalyl Thio-propyl (2- (butoxyethoxy) ethoxy) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-decyloxalylthio-propyl (2- (butoxyethoxy) ethoxy) 1,3-dioxa- 6-Butylaza-2-silacyclooctane, 3-dodecyloxalylthio-propyl (2- (butoxyethoxy) ethoxy) 1,3-dioxa-6-butyl Tilaza-2-silacyclooctane,

  3-Methyloxalylthio-propyl (methyl) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-ethyloxalylthio-propyl (methyl) 1,3-dioxa-6-butylaza-2-silacyclo Octane, 3-pentyloxalylthio-propyl (methyl) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-octyloxalylthio-propyl (methyl) 1,3-dioxa-6-butylaza-2- Silacyclooctane, 3-decyloxalylthio-propyl (methyl) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-dodecyloxalylthio-propyl (methyl) 1,3-dioxa-6-butylaza- 2-silacyclooctane,

  3-methyloxalylthio-propyl (ethyl) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-ethyloxalylthio-propyl (ethyl) 1,3-dioxa-6-butylaza-2-silacyclo Octane, 3-pentyloxalylthio-propyl (ethyl) 1,3-dioxa-6 butylaza-2-silacyclooctane, 3-octyloxalylthio-propyl (ethyl) 1,3-dioxa-6-butylaza-2-sila Cyclooctane, 3-decyloxalylthio-propyl (ethyl) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-dodecyloxalylthio-propyl (ethyl) 1,3-dioxa-6-butylaza-2 -Silacyclooctane,

  3-Methyloxalylthio-propyl (decyl) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-ethyloxalylthio-propyl (decyl) 1,3-dioxa-6-butylaza-2-silacyclo Octane, 3-pentyloxalylthio-propyl (decyl) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-octyloxalylthio-propyl (decyl) 1,3-dioxa-6-butylaza-2- Silacyclooctane, 3-decyloxalylthio-propyl (decyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-dodecyloxalylthio-propyl (decyl) 1,3-dioxa-6-butylaza- 2-silacyclooctane,

  3-Methyloxalylthio-propyl (ethoxy) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-ethyloxalylthio-propyl (ethoxy) 1,3-dioxa-6-dodecylaza-2-silacyclo Octane, 3-pentyloxalylthio-propyl (ethoxy) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-octyloxalylthio-propyl (ethoxy) 1,3-dioxa-6-dodecylaza-2- Silacyclooctane, 3-decyloxalylthio-propyl (ethoxy) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-dodecyloxalylthio-propyl (ethoxy) 1,3-dioxa-6-dodecylaza- 2-silacyclooctane,

  3-Methyloxalylthio-propyl (methoxy) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-ethyloxalylthio-propyl (methoxy) 1,3-dioxa-6-dodecylaza-2-silacyclo Octane, 3-pentyloxalylthio-propyl (methoxy) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-octyloxalylthio-propyl (methoxy) 1,3-dioxa-6-dodecylaza-2- Silacyclooctane, 3-decyloxalylthio-propyl (methoxy) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-dodecyloxalylthio-propyl (methoxy) 1,3-dioxa-6-dodecylaza- 2-silacyclooctane,

  3-Methyloxalylthio-propyl (butoxy) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-ethyloxalylthio-propyl (butoxy) 1,3-dioxa-6-dodecylaza-2-silacyclo Octane, 3-pentyloxalylthio-propyl (butoxy) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-octyloxalylthio-propyl (butoxy) 1,3-dioxa-6-dodecylaza-2- Silacyclooctane, 3-decyloxalylthio-propyl (butoxy) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-dodecyloxalylthio-propyl (butoxy) 1,3-dioxa-6-butylaza- 2-silacyclooctane,

  3-Methyloxalylthio-propyl (decanoxy) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-ethyloxalylthio-propyl (decanoxy) 1,3-dioxa-6-dodecylaza-2-silacyclo Octane, 3-pentyloxalylthio-propyl (decanoxy) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-octyloxalylthio-propyl (decanoxy) 1,3-dioxa-6-dodecylaza-2- Silacyclooctane, 3-decyloxalylthio-propyl (decanoxy) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-dodecyloxalylthio-propyl (decanoxy) 1,3-dioxa-6-dodecylaza- 2-silacyclooctane,

  3-methyloxalylthio-propyl (2- (butoxyethoxy) ethoxy) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-ethyloxalylthio-propyl (2- (butoxyethoxy) ethoxy) 1, 3-Dioxa-6-dodecylaza-2-silacyclooctane, 3-pentyloxalylthio-propyl (2- (butoxyethoxy) ethoxy) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-octyloxalyl Thio-propyl (2- (butoxyethoxy) ethoxy) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-decyloxalylthio-propyl (2- (butoxyethoxy) ethoxy) 1,3-dioxa- 6-dodecylaza-2-silacyclooctane, 3-dodecyloxalylthio-propyl (2- (butoxyethoxy) ethoxy) 1,3-di Kisa -6 dodecylaza-2-silacyclooctane,

  3-Methyloxalylthio-propyl (methyl) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-ethyloxalylthio-propyl (methyl) 1,3-dioxa-6-dodecylaza-2-silacyclo Octane, 3-pentyloxalylthio-propyl (methyl) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-octyloxalylthio-propyl (methyl) 1,3-dioxa-6-dodecylaza-2- Silacyclooctane, 3-decyloxalylthio-propyl (methyl) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-dodecyloxalylthio-propyl (methyl) 1,3-dioxa-6-dodecylaza- 2-silacyclooctane,

  3-Methyloxalylthio-propyl (ethyl) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-ethyloxalylthio-propyl (ethyl) 1,3-dioxa-6-dodecylaza-2-silacyclo Octane, 3-pentyloxalylthio-propyl (ethyl) 1,3-dioxa-6 dodecylaza-2-silacyclooctane, 3-octyloxalylthio-propyl (ethyl) 1,3-dioxa-6-dodecylaza-2-sila Cyclooctane, 3-decyloxalylthio-propyl (ethyl) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-dodecyloxalylthio-propyl (ethyl) 1,3-dodecyl-6-dodecylaza-2 -Silacyclooctane,

  3-Methyloxalylthio-propyl (decyl) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-ethyloxalylthio-propyl (decyl) 1,3-dioxa-6-dodecylaza-2-silacyclo Octane, 3-pentyloxalylthio-propyl (decyl) 1,3-dioxa-6 dodecylaza-2-silacyclooctane, 3-octyloxalylthio-propyl (decyl) 1,3-dioxa-6 dodecylaza-2-silacyclo Octane, 3-decyloxalylthio-propyl (decyl) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-dodecyloxalylthio-propyl (decyl) 1,3-dioxa-6-dodecylaza-2- Silacyclooctane,

  3-methyloxalylthio-propyl (didimethylaminoethoxy) ethoxysilane, 3-ethyloxalylthio-propyl (didimethylaminoethoxy) ethoxysilane, 3-pentyloxalylthio-propyl (didimethylaminoethoxy) ethoxysilane, 3- Octyloxalylthio-propyl (didimethylaminoethoxy) ethoxysilane, 3-decyloxalylthio-propyl (didimethylaminoethoxy) ethoxysilane, 3-dodecyloxalylthio-propyl (didimethylaminoethoxy) ethoxysilane,

  3-methyloxalylthio-propyl (dimethylaminoethoxy) diethoxysilane, 3-ethyloxalylthio-propyl (dimethylaminoethoxy) diethoxysilane, 3-pentyloxalylthio-propyl (dimethylaminoethoxy) diethoxysilane, 3- Octyloxalylthio-propyl (dimethylaminoethoxy) diethoxysilane, 3-decyloxalylthio-propyl (dimethylaminoethoxy) diethoxysilane, 3-dodecyloxalylthio-propyl (dimethylaminoethoxy) diethoxysilane,

  3-methyloxalylthio-propyl (didiethylaminoethoxy) ethoxysilane, 3-ethyloxalylthio-propyl (didiethylaminoethoxy) ethoxysilane, 3-pentyloxalylthio-propyl (didiethylaminoethoxy) ethoxysilane, 3-octyloxalylthio -Propyl (didiethylaminoethoxy) ethoxysilane, 3-decyloxalylthio-propyl (didiethylaminoethoxy) ethoxysilane, 3-dodecyloxalylthio-propyl (didiethylaminoethoxy) ethoxysilane,

  3-methyloxalylthio-propyl (diethylaminoethoxy) diethoxysilane, 3-ethyloxalylthio-propyl (diethylaminoethoxy) diethoxysilane, 3-pentyloxalylthio-propyl (diethylaminoethoxy) diethoxysilane, 3-octyloxalylthio -Propyl (diethylaminoethoxy) diethoxysilane, 3-decyloxalylthio-propyl (diethylaminoethoxy) diethoxysilane, 3-dodecyloxalylthio-propyl (diethylaminoethoxy) diethoxysilane,

  3-methyloxalylthio-propyl (didibutylaminoethoxy) ethoxysilane, 3-ethyloxalylthio-propyl (didibutylaminoethoxy) ethoxysilane, 3-pentyloxalylthio-propyl (didibutylaminoethoxy) ethoxysilane, 3- Octyloxalylthio-propyl (didibutylaminoethoxy) ethoxysilane, 3-decyloxalylthio-propyl (didibutylaminoethoxy) ethoxysilane, 3-dodecyloxalylthio-propyl (didibutylaminoethoxy) ethoxysilane,

  3-methyloxalylthio-propyl (dibutylaminoethoxy) diethoxysilane, 3-ethyloxalylthio-propyl (dibutylaminoethoxy) diethoxysilane, 3-pentyloxalylthio-propyl (dibutylaminoethoxy) diethoxysilane, 3- Octyloxalylthio-propyl (dibutylaminoethoxy) diethoxysilane, 3-decyloxalylthio-propyl (dibutylaminoethoxy) diethoxysilane, 3-dodecyloxalylthio-propyl (dibutylaminoethoxy) diethoxysilane,

  3-methyloxalylthio-propyl (dididecylaminoethoxy) ethoxysilane, 3-ethyloxalylthio-propyl (dididecylaminoethoxy) ethoxysilane, 3-pentyloxalylthio-propyl (dididecylaminoethoxy) ethoxysilane, 3- Octyloxalylthio-propyl (dididecylaminoethoxy) ethoxysilane, 3-decyloxalylthio-propyl (dididecylaminoethoxy) ethoxysilane, 3-dodecyloxalylthio-propyl (dididecylaminoethoxy) ethoxysilane,

  3-Methyloxalylthio-propyl (didecylaminoethoxy) diethoxysilane, 3-ethyloxalylthio-propyl (didecylaminoethoxy) diethoxysilane, 3-pentyloxalylthio-propyl (didecylaminoethoxy) diethoxysilane 3-octyloxalylthio-propyl (didecylaminoethoxy) diethoxysilane, 3-decyloxalylthio-propyl (didecylaminoethoxy) diethoxysilane, 3-dodecyloxalylthio-propyl (didecylaminoethoxy) diethoxy Silane,

  3-methyloxalylthio-propyl (dididodecylaminoethoxy) ethoxysilane, 3-ethyloxalylthio-propyl (dididodecylaminoethoxy) ethoxysilane, 3-pentyloxalylthio-propyl (dididodecylaminoethoxy) ethoxysilane, 3- Octyloxalylthio-propyl (dididodecylaminoethoxy) ethoxysilane, 3-decyloxalylthio-propyl (dididodecylaminoethoxy) ethoxysilane, 3-dodecyloxalylthio-propyl (dididodecylaminoethoxy) ethoxysilane,

  3-Methyloxalylthio-propyl (didodecylaminoethoxy) diethoxysilane, 3-ethyloxalylthio-propyl (didodecylaminoethoxy) diethoxysilane, 3-pentyloxalylthio-propyl (didodecylaminoethoxy) diethoxysilane 3-octyloxalylthio-propyl (didodecylaminoethoxy) diethoxysilane, 3-decyloxalylthio-propyl (didodecylaminoethoxy) diethoxysilane, 3-dodecyloxalylthio-propyl (didodecylaminoethoxy) diethoxy Silane,

  3-methyloxalylthio-propyl (didimethylaminoethoxy) methylsilane, 3-ethyloxalylthio-propyl (didimethylaminoethoxy) methylsilane, 3-pentyloxalylthio-propyl (didimethylaminoethoxy) methylsilane, 3-octyloxalylthio -Propyl (didimethylaminoethoxy) methylsilane, 3-decyloxalylthio-propyl (didimethylaminoethoxy) methylsilane, 3-dodecyloxalylthio-propyl (didimethylaminoethoxy) methylsilane,

  3-methyloxalylthio-propyl (didiethylaminoethoxy) methylsilane, 3-ethyloxalylthio-propyl (didiethylaminoethoxy) methylsilane, 3-pentyloxalylthio-propyl (didiethylaminoethoxy) methylsilane, 3-octyloxalylthio-propyl ( Didiethylaminoethoxy) methylsilane, 3-decyloxalylthio-propyl (didiethylaminoethoxy) methylsilane, 3-dodecyloxalylthio-propyl (didiethylaminoethoxy) methylsilane,

  3-methyloxalylthio-propyl (didibutylaminoethoxy) methylsilane, 3-ethyloxalylthio-propyl (didibutylaminoethoxy) methylsilane, 3-pentyloxalylthio-propyl (didibutylaminoethoxy) methylsilane, 3-octyloxalylthio -Propyl (didibutylaminoethoxy) methylsilane, 3-decyloxalylthio-propyl (didibutylaminoethoxy) methylsilane, 3-dodecyloxalylthio-propyl (didibutylaminoethoxy) methylsilane,

  3-methyloxalylthio-propyl (dididecylaminoethoxy) methylsilane, 3-ethyloxalylthio-propyl (dididecylaminoethoxy) methylsilane, 3-pentyloxalylthio-propyl (dididecylaminoethoxy) methylsilane, 3-octyloxalylthio -Propyl (dididecylaminoethoxy) methylsilane, 3-decyloxalylthio-propyl (dididecylaminoethoxy) methylsilane, 3-dodecyloxalylthio-propyl (dididecylaminoethoxy) methylsilane,

  3-methyloxalylthio-propyl (dididodecylaminoethoxy) methylsilane, 3-ethyloxalylthio-propyl (dididodecylaminoethoxy) methylsilane, 3-pentyloxalylthio-propyl (dididodecylaminoethoxy) methylsilane, 3-octyloxalylthio -Propyl (dididodecylaminoethoxy) methylsilane, 3-decyloxalylthio-propyl (dididodecylaminoethoxy) methylsilane, 3-dodecyloxalylthio-propyl (dididodecylaminoethoxy) methylsilane,

  3-methyloxalylthio-propyl (didimethylaminoethoxy) decanoxysilane, 3-ethyloxalylthio-propyl (didimethylaminoethoxy) decanoxysilane, 3-pentyloxalylthio-propyl (didimethylaminoethoxy) decanoxysilane, 3-octyloxalylthio -Propyl (didimethylaminoethoxy) decanoxysilane, 3-decyloxalylthio-propyl (didimethylaminoethoxy) decanoxysilane, 3-dodecyloxalylthio-propyl (didimethylaminoethoxy) decanoxysilane,

  3-Methyloxalylthio-propyl (dimethylaminoethoxy) didecanoxysilane, 3-ethyloxalylthio-propyl (dimethylaminoethoxy) didecanoxysilane, 3-pentyloxalylthio-propyl (dimethylaminoethoxy) didecanoxysilane 3-octyloxalylthio-propyl (dimethylaminoethoxy) didecanoxysilane, 3-decyloxalylthio-propyl (dimethylaminoethoxy) didecanoxysilane, 3-dodecyloxalylthio-propyl (dimethylaminoethoxy) didecanoxy Silane,

  3-methyloxalylthio-propyl (didiethylaminoethoxy) decanoxysilane, 3-ethyloxalylthio-propyl (didiethylaminoethoxy) decanoxysilane, 3-pentyloxalylthio-propyl (didiethylaminoethoxy) decanoxysilane, 3-octyloxalylthio-propyl ( Didiethylaminoethoxy) decanoxysilane, 3-decyloxalylthio-propyl (didiethylaminoethoxy) decanoxysilane, 3-dodecyloxalylthio-propyl (didiethylaminoethoxy) decanoxysilane,

  3-methyloxalylthio-propyl (diethylaminoethoxy) didecanoxysilane, 3-ethyloxalylthio-propyl (diethylaminoethoxy) didecanoxysilane, 3-pentyloxalylthio-propyl (diethylaminoethoxy) didecanoxysilane, 3- Octyloxalylthio-propyl (diethylaminoethoxy) didecanoxysilane, 3-decyloxalylthio-propyl (diethylaminoethoxy) didecanoxysilane, 3-dodecyloxalylthio-propyl (diethylaminoethoxy) didecanoxysilane,

  3-methyloxalylthio-propyl (didibutylaminoethoxy) decanoxysilane, 3-ethyloxalylthio-propyl (didibutylaminoethoxy) decanoxysilane, 3-pentyloxalylthio-propyl (didibutylaminoethoxy) decanoxysilane, 3-octyloxalylthio -Propyl (didibutylaminoethoxy) decanoxysilane, 3-decyloxalylthio-propyl (didibutylaminoethoxy) decanoxysilane, 3-dodecyloxalylthio-propyl (didibutylaminoethoxy) decanoxysilane,

  3-methyloxalylthio-propyl (dibutylaminoethoxy) didecanoxysilane, 3-ethyloxalylthio-propyl (dibutylaminoethoxy) didecanoxysilane, 3-pentyloxalylthio-propyl (dibutylaminoethoxy) didecanoxysilane 3-octyloxalylthio-propyl (dibutylaminoethoxy) didecanoxysilane, 3-decyloxalylthio-propyl (dibutylaminoethoxy) didecanoxysilane, 3-dodecyloxalylthio-propyl (dibutylaminoethoxy) didecanoxy Silane,

  3-methyloxalylthio-propyl (dididecylaminoethoxy) decanoxysilane, 3-ethyloxalylthio-propyl (dididecylaminoethoxy) decanoxysilane, 3-pentyloxalylthio-propyl (dididecylaminoethoxy) decanoxysilane, 3-octyloxalylthio -Propyl (dididecylaminoethoxy) decanoxysilane, 3-decyloxalylthio-propyl (dididecylaminoethoxy) decanoxysilane, 3-dodecyloxalylthio-propyl (dididecylaminoethoxy) decanoxysilane,

  3-Methyloxalylthio-propyl (didecylaminoethoxy) didecanoxysilane, 3-ethyloxalylthio-propyl (didecylaminoethoxy) didecanoxysilane, 3-pentyloxalylthio-propyl (didecylaminoethoxy) dide Canoxysilane, 3-octyloxalylthio-propyl (didecylaminoethoxy) didecanoxysilane, 3-decyloxalylthio-propyl (didecylaminoethoxy) didecanoxysilane, 3-dodecyloxalylthio-propyl (didecyl) Aminoethoxy) didecanoxysilane,

  3-methyloxalylthio-propyl (dididodecylaminoethoxy) decanoxysilane, 3-ethyloxalylthio-propyl (dididodecylaminoethoxy) decanoxysilane, 3-pentyloxalylthio-propyl (dididodecylaminoethoxy) decanoxysilane, 3-octyloxalylthio -Propyl (dididodecylaminoethoxy) decanoxysilane, 3-decyloxalylthio-propyl (dididodecylaminoethoxy) decanoxysilane, 3-dodecyloxalylthio-propyl (dididodecylaminoethoxy) decanoxysilane,

  3-methyloxalylthio-propyl (didodecylaminoethoxy) didecanoxysilane, 3-ethyloxalylthio-propyl (didodecylaminoethoxy) didecanoxysilane, 3-pentyloxalylthio-propyl (didodecylaminoethoxy) dide Canoxysilane, 3-octyloxalylthio-propyl (didodecylaminoethoxy) didecanoxysilane, 3-decyloxalylthio-propyl (didodecylaminoethoxy) didecanoxysilane, 3-dodecyloxalylthio-propyl (didodecyl) Aminoethoxy) didecanoxysilane,

  3-methyloxalylthio-propyl (didimethylaminoethoxy) -2- (butoxyethoxy) ethoxysilane, 3-ethyloxalylthio-propyl (didimethylaminoethoxy) -2- (butoxyethoxy) ethoxysilane, 3-pentyloxalyl Thio-propyl (didimethylaminoethoxy) -2- (butoxyethoxy) ethoxysilane, 3-octyloxalylthio-propyl (didimethylaminoethoxy) -2- (butoxyethoxy) ethoxysilane, 3-decyloxalylthio-propyl ( Didimethylaminoethoxy) -2- (butoxyethoxy) ethoxysilane, 3-dodecyloxalylthio-propyl (didimethylaminoethoxy) -2- (butoxyethoxy) ethoxysilane,

  3-methyloxalylthio-propyl (didiethylaminoethoxy) -2- (butoxyethoxy) ethoxysilane, 3-ethyloxalylthio-propyl (didiethylaminoethoxy) -2- (butoxyethoxy) ethoxysilane, 3-pentyloxalylthio- Propyl (didiethylaminoethoxy) -2- (butoxyethoxy) ethoxysilane, 3-octyloxalylthio-propyl (didiethylaminoethoxy) -2- (butoxyethoxy) ethoxysilane, 3-decyloxalylthio-propyl (didiethylaminoethoxy) 2- (butoxyethoxy) ethoxysilane, 3-dodecyloxalylthio-propyl (didiethylaminoethoxy) -2- (butoxyethoxy) ethoxysilane,

  3-methyloxalylthio-propyl (didibutylaminoethoxy) -2- (butoxyethoxy) ethoxysilane, 3-ethyloxalylthio-propyl (didibutylaminoethoxy) -2- (butoxyethoxy) ethoxysilane, 3-pentyloxalyl Thio-propyl (didibutylaminoethoxy) -2- (butoxyethoxy) ethoxysilane, 3-octyloxalylthio-propyl (didibutylaminoethoxy) -2- (butoxyethoxy) ethoxysilane, 3-decyloxalylthio-propyl ( Didibutylaminoethoxy) -2- (butoxyethoxy) ethoxysilane, 3-dodecyloxalylthio-propyl (didibutylaminoethoxy) -2- (butoxyethoxy) ethoxysilane,

  3-methyloxalylthio-propyl (dididecylaminoethoxy) -2- (butoxyethoxy) ethoxysilane, 3-ethyloxalylthio-propyl (dididecylaminoethoxy) -2- (butoxyethoxy) ethoxysilane, 3-pentyloxalyl Thio-propyl (dididecylaminoethoxy) -2- (butoxyethoxy) ethoxysilane, 3-octyloxalylthio-propyl (dididecylaminoethoxy) -2- (butoxyethoxy) ethoxysilane, 3-decyloxalylthio-propyl ( Dididecylaminoethoxy) -2- (butoxyethoxy) ethoxysilane, 3-dodecyloxalylthio-propyl (dididecylaminoethoxy) -2- (butoxyethoxy) ethoxysilane,

  3-methyloxalylthio-propyl (dididodecylaminoethoxy) -2- (butoxyethoxy) ethoxysilane, 3-ethyloxalylthio-propyl (dididodecylaminoethoxy) -2- (butoxyethoxy) ethoxysilane, 3-pentyloxalyl Thio-propyl (dididodecylaminoethoxy) -2- (butoxyethoxy) ethoxysilane, 3-octyloxalylthio-propyl (dididodecylaminoethoxy) -2- (butoxyethoxy) ethoxysilane, 3-decyloxalylthio-propyl ( Dididodecylaminoethoxy) -2- (butoxyethoxy) ethoxysilane, 3-dodecyloxalylthio-propyl (dididodecylaminoethoxy) -2- (butoxyethoxy) ethoxysilane.

<< Method for Synthesizing Organosilicon Compound of the Present Invention >>
The organosilicon compound of the present invention is represented by, for example, the above general formula (I), R ¹ , R ^2, and R ³ are represented by —M—C ₁ H _{2 l + 1} , and R ¹ , R ² And a compound in which one or more of M in R ³ is —O—, 2- (dimethylamino) ethanol, 2- (diethylamino) ethanol, 2- (dimethylamino) propanol, 2- (diethylamino) propanol, An amine compound such as N-methyldiethanolamine is added, and an acid such as p-toluenesulfonic acid and hydrochloric acid as a catalyst, and a titanium alkoxide such as titanium tetra-n-butoxide are added and heated, and R ¹ , R ² and R ^{3 are} heated. One or more of them are substituted with a monovalent nitrogen-containing group represented by formula (II) or formula (III), or R ¹ and R ² are divalent nitrogen-containing represented by —R ¹² —W—R ¹³ — It can be synthesized by substituting with a group.

[Rubber composition]
The rubber composition of the present invention is obtained by blending an inorganic filler (B) and the above-mentioned organosilicon compound (C) with a rubber component (A) made of natural rubber and / or a diene synthetic rubber. Preferably, the rubber component (A) composed of natural rubber and / or diene synthetic rubber is blended with 5 to 140 parts by weight of the inorganic filler (B), and the above organic The silicon compound (C) is blended in an amount of 1 to 20% by mass based on the blending amount of the inorganic filler (B).

Here, when the content of the organosilicon compound (C) is less than 1% by mass of the blending amount of the inorganic filler (B), the effect of reducing the hysteresis loss of the rubber composition and the effect of improving the wear resistance are ineffective. On the other hand, if it exceeds 20% by mass, the effect is saturated.

The rubber component (A) of the rubber composition of the present invention comprises natural rubber and / or a diene synthetic rubber. Here, as the diene-based synthetic rubber, styrene-butadiene copolymer rubber (SBR)
, Polybutadiene rubber (BR), polyisoprene rubber (IR), butyl rubber (IIR), ethylene-propylene copolymer, and the like. These rubber components (A) may be used alone or in a blend of two or more.

  Examples of the inorganic filler (B) used in the rubber composition of the present invention include silica, aluminum hydroxide, alumina, clay, calcium carbonate, etc. Among these, silica and aluminum hydroxide are preferable from the viewpoint of reinforcement. Silica is preferred and particularly preferred. When the inorganic filler (B) is silica, the organosilicon compound (C) has a functional group having a high affinity for the silanol group on the silica surface and / or a functional group having a high affinity for the silicon atom (Si). For this reason, the coupling efficiency is greatly improved, the hysteresis loss of the rubber composition is reduced, and the effect of improving the wear resistance becomes more remarkable. In addition, there is no restriction | limiting in particular as silica, Wet silica (hydrous silicic acid), dry-type silica (anhydrous silicic acid), etc. can be used, On the other hand, as aluminum hydroxide, Heidilite (registered trademark, Showa Denko) Are preferably used.

The silica is preferably BET surface area of 40~350 m ² / g. When the BET surface area of silica is less than 40 m ² / g, the wear resistance is greatly reduced because the particle diameter of the silica is too large, and when the BET surface area of silica exceeds 350 m ² / g, Since the particle diameter of the silica is too small, hysteresis loss is greatly increased.

  The compounding quantity of the said inorganic filler (B) is the range of 5-140 mass parts with respect to 100 mass parts of said rubber components (A). If the blending amount of the inorganic filler (B) is less than 5 parts by mass with respect to 100 parts by mass of the rubber component (A), the effect of reducing the hysteresis is insufficient, while if it exceeds 140 parts by mass, the workability is increased. This is because of the remarkable deterioration.

  In addition to the rubber component (A), inorganic filler (B), and organosilicon compound (C), the rubber composition of the present invention contains compounding agents commonly used in the rubber industry, such as carbon black, softeners. Vulcanizing agents, vulcanization accelerators, anti-aging agents, zinc white, stearic acid and the like can be appropriately blended depending on the purpose. As these compounding agents, commercially available products can be suitably used. In addition, the rubber composition of the present invention is blended with the rubber component (A), together with the inorganic filler (B) and the organosilicon compound (C), and various compounding agents appropriately selected as necessary. It can be produced by hot-pressing, extruding or the like.

[tire]
The tire of the present invention is characterized by using the above rubber composition, and the above rubber composition is preferably used for the tread. In the tire of the present invention, the rolling resistance is greatly reduced, and the wear resistance is also greatly improved. The tire of the present invention has a conventionally known structure and is not particularly limited, and can be produced by a normal method. In addition, when the tire of the present invention is a pneumatic tire, the gas filled in the tire may be normal or air with adjusted oxygen partial pressure, or an inert gas such as nitrogen, argon, or helium. .

[Primer composition, coating composition and adhesive composition]
Furthermore, the primer composition, the coating composition and the adhesive composition of the present invention are characterized by containing the above-mentioned organosilicon compound, and for various work members such as glass, various painted surfaces, and porous surfaces. Good undercoat characteristics, coating properties, and adhesiveness can be sufficiently exhibited.

  Hereinafter, the present invention will be described in more detail with reference to examples. However, the present invention is not limited to the following examples.

[Organic silicon compound in the first embodiment of the present invention]
<Production Example 1-1 of Organosilicon Compound>
In a 1 L four-necked eggplant flask, 23.8 g of 3-mercaptopropyltriethoxysilane and 11.1 g of triethylamine were dissolved in 300 mL of toluene under a nitrogen atmosphere. To this solution, 10.8 g of methoxyacetyl chloride was added dropwise over 30 minutes and stirred for 2 hours. Thereafter, the precipitate was filtered off and the solvent was removed by a rotary evaporator at 20 hPa / 40 ° C., and an organosilicon compound (C1-1) (C ₁₂ H ₂₆ O ₅ SSi represented by the following formula: molecular weight 310.48, 29.5 g of 3-methoxyethanoylthio-propyltriethoxysilane) was obtained.
¹ H-NMR (CDCl3, 700 MHz, δ; ppm) = 4.7 (s; 2H), 3.8 (q; 6H), 3.4 (s; 3H), 3.0 (t; 2H), 1.8 (m; 2H), 1.2 (t; 9H), 0.7 (t; 2H)

<Production Example 2-1 of Organosilicon Compound>
In a 1 L four-necked eggplant flask, 23.8 g of 3-mercaptopropyltriethoxysilane and 11.1 g of triethylamine were dissolved in 300 mL of toluene under a nitrogen atmosphere. To this solution, 17.0 g of phenoxyacetyl chloride was added dropwise over 30 minutes and stirred for 2 hours. Thereafter, the precipitate was filtered off and the solvent was removed by a rotary evaporator at 20 hPa / 40 ° C., and the organosilicon compound (C2-1) (C ₁₇ H ₂₈ O ₅ SSi, molecular weight 372.55 represented by the following formula: 35.0 g of 3-phenoxyethanoylthio-propyltriethoxysilane) was obtained.
¹ H-NMR (CDCl3, 700 MHz, δ; ppm) = 7.2 (t; 2H), 7.0 (t; 1H), 6.9 (d; 2H), 4.7 (s; 2H), 3.8 (q; 6H), 3.4 (s; 3H), 3.0 (t; 2H), 1.8 (m; 2H), 1.2 (t; 9H), 0.7 (t; 2H)

<Production Example 3-1 of Organosilicon Compound>
In a 500 mL four-necked eggplant flask, 31.0 g of 3-methoxyethanoylthio-propyltriethoxysilane, 11.9 g of N-methyldiethanolamine, and 0.05 g of titanium tetra-n-butoxide were dissolved in 200 mL of xylene under a nitrogen atmosphere. The temperature was raised to 150 ° C. and stirred for 6 hours. Then, the solvent was removed with a rotary evaporator at 20 hPa / 40 ° C, and then the remaining volatile components were removed with a rotary pump (10 Pa) and a cold trap (dry ice + ethanol). Organosilicon compound (C3-1) (C ₁₃ H ₂₇ NO ₅ SSi, molecular weight 337.51, 3-methoxyethanoylthio-propyl (ethoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane) 30.7 g Got.
¹ H-NMR (CDCl3, 700 MHz, δ; ppm) = 4.7 (s; 2H), 3.8 (m; 6H), 3.4 (s; 3H), 3.0 (t; 2H), 2.6 (t; 4H), 2.3 (s; 3H), 1.8 (m; 2H), 1.2 (t; 3H), 0.7 (t; 2H)

<Production example 4-1 of organosilicon compound>
In a 500 mL four-necked eggplant flask, 31.0 g of 3-phenoxyethanoylthio-propyltriethoxysilane, 11.9 g of N-methyldiethanolamine, and 0.05 g of titanium tetra-n-butoxide were dissolved in 200 mL of xylene under a nitrogen atmosphere. The temperature was raised to 150 ° C. and stirred for 6 hours. Then, the solvent was removed with a rotary evaporator at 20 hPa / 40 ° C, and then the remaining volatile components were removed with a rotary pump (10 Pa) and a cold trap (dry ice + ethanol). 30.7 g of an organosilicon compound (C4-1) (C ₁₈ H ₂₉ NO ₅ SSi, molecular weight 399.58, 3-phenoxyethanoylthio-propyl (ethoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane) Obtained.
¹ H-NMR (CDCl3, 700 MHz, δ; ppm) = 7.2 (t; 2H), 7.0 (t; 1H), 6.9 (d; 2H), 4.7 (s; 2H), 3.8 (q; 6H), 3.0 (t; 2H), 2.6 (t; 4H), 2.3 (s; 3H), 1.8 (m; 2H), 1.2 (t; 3H), 0.7 (t; 2H)

<Production Example 5-1 of Organosilicon Compound>
In a 1 L four-necked eggplant flask, 18.0 g of 3-mercaptopropyldimethoxymethylsilane and 11.1 g of triethylamine were dissolved in 300 mL of toluene under a nitrogen atmosphere. To this solution, 17.0 g of phenoxyacetyl chloride was added dropwise over 30 minutes and stirred for 2 hours. Thereafter, the precipitate was filtered off and the solvent was removed by a rotary evaporator at 20 hPa / 40 ° C. to obtain 29.7 g of 3-phenoxyethanoylthio-propyldimethoxymethylsilane.
¹ H-NMR (CDCl3, 700 MHz, δ; ppm) = 7.2 (t; 2H), 7.0 (t; 1H), 6.9 (d; 2H), 4.7 (s; 2H), 3.0 (t; 2H), 2.5 (s; 6H), 1.8 (m; 2H), 0.7 (t; 2H), 0.1 (s; 3H)

Subsequently, 29.7 g of 3-phenoxyethanoylthio-propyldimethoxymethylsilane, 11.2 g of N-methyldiethanolamine, and 0.05 g of titanium tetra-n-butoxide were dissolved in 200 mL of xylene in a 500 mL four-necked eggplant flask. The temperature was raised to 150 ° C. and stirred for 2 hours. Then, the solvent was removed with a rotary evaporator at 20 hPa / 40 ° C, and then the remaining volatile components were removed with a rotary pump (10 Pa) and a cold trap (dry ice + ethanol). 31.1 g of an organosilicon compound (C5-1) (C ₁₇ H ₂₇ NO ₄ SSi, molecular weight 369.55, 3-phenoxyethanoylthio-propyl (methyl) 1,3-dioxa-6-methylaza-2-silacyclooctane) Obtained.
¹ H-NMR (CDCl3, 700 MHz, δ; ppm) = 7.2 (t; 2H), 7.0 (t; 1H), 6.9 (d; 2H), 4.7 (s; 2H), 3.8 (t; 4H), 3.0 (t; 2H), 2.6 (t; 4H), 2.3 (s; 3H), 1.8 (m; 2H), 0.7 (t; 2H), 0.1 (s; 3H)

<Production Example 6-1 of organosilicon compound>
In a 500 mL four-necked eggplant flask, 31.4 g of 3-phenoxyethanoylthio-propyldimethoxymethylsilane, 17.8 g of N-dimethylaminoethanol, and 0.05 g of titanium tetra-n-butoxide were dissolved in 200 mL of xylene under a nitrogen atmosphere. The temperature was raised to 150 ° C. and stirred for 2 hours. Then, the solvent was removed with a rotary evaporator at 20 hPa / 40 ° C, and then the remaining volatile components were removed with a rotary pump (10 Pa) and a cold trap (dry ice + ethanol). that the organosilicon compound (C6-1) - was obtained _{(C 20 H 36 N 2 O} 4 SSi, molecular weight 428.66,3- diphenoxyethane data Noi thio propyl (di dimethylaminoethoxy) methylsilane) 40.0 g.
¹ H-NMR (CDCl3, 700 MHz, δ; ppm) = 4.7 (s; 2H), 3.8 (q; 6H), 3.4 (s; 3H), 3.0 (t; 2H), 1.8 (m; 2H), 1.2 (t; 9H), 0.7 (t; 2H)

<Production Example 7-1 of Organosilicon Compound>
In a 500 mL four-necked eggplant flask, 31.4 g of 3-phenoxyethanoylthio-propyldimethoxymethylsilane, 16.1 g of N-butyldiethanolamine, and 0.05 g of titanium tetra-n-butoxide were dissolved in 200 mL of xylene under a nitrogen atmosphere. The temperature was raised to 150 ° C. and stirred for 2 hours. Then, the solvent was removed with a rotary evaporator at 20 hPa / 40 ° C, and then the remaining volatile components were removed with a rotary pump (10 Pa) and a cold trap (dry ice + ethanol). 39.5 g of organosilicon compound (C7-1) (C ₂₀ H ₃₃ NO ₄ SSi, molecular weight 411.63, 3-phenoxyethanoylthio-propyl (methyl) 1,3-dioxa-6-butylaza-2-silacyclooctane) Obtained.
¹ H-NMR (CDCl3, 700 MHz, δ; ppm) = 7.2 (t; 2H), 7.0 (t; 1H), 6.9 (d; 2H), 4.7 (s; 2H), 3.8 (t; 4H), 3.0 (t; 2H), 2.6 (t; 4H), 2.3 (t; 2H), 1.8 (m; 2H), 1.4 (m; 2H), 1.3 (m; 2H), 0.9 (t; 3H), 0.7 ( t; 2H), 0.1 (s; 3H)

<Production Example 8-1 of organosilicon compound>
In a 500 mL four-necked eggplant flask, 31.4 g of 3-phenoxyethanoylthio-propyldimethoxymethylsilane, 27.3 g of N-lauryldiethanolamine, and 0.05 g of titanium tetra-n-butoxide were dissolved in 200 mL of xylene in a nitrogen atmosphere. The temperature was raised to 150 ° C. and stirred for 2 hours. Then, the solvent was removed with a rotary evaporator at 20 hPa / 40 ° C, and then the remaining volatile components were removed with a rotary pump (10 Pa) and a cold trap (dry ice + ethanol). 49.3 g of an organosilicon compound (C8-1) (C ₂₈ H ₄₉ NO ₄ SSi, molecular weight 523.84, 3-phenoxyethanoylthio-propyl (methyl) 1,3-dioxa-6-dodecylaza-2-silacyclooctane) Obtained.
¹ H-NMR (CDCl3, 700 MHz, δ; ppm) = 7.2 (t; 2H), 7.0 (t; 1H), 6.9 (d; 2H), 4.7 (s; 2H), 3.8 (t; 4H), 3.0 (t; 2H), 2.6 (t; 4H), 2.3 (t; 2H), 1.8 (m; 2H), 1.4 (m; 2H), 1.3 (m; 18H), 0.9 (t; 3H), 0.7 ( t; 2H), 0.1 (s; 3H)

<Production Example 9-1 of Organosilicon Compound>
In a 500 mL four-necked eggplant flask, 23.8 g of 3-mercapto-propyltriethoxysilane, 11.9 g of N-methyldiethanolamine, and 0.05 g of titanium tetra-n-butoxide were dissolved in 200 mL of xylene under a nitrogen atmosphere. The temperature was raised to 150 ° C. and stirred for 6 hours. Subsequently, 15.8 g of decyl alcohol was added dropwise and stirred for 2 hours. Thereafter, the solvent was removed by a rotary evaporator at 20 hPa / 40 ° C., and then the remaining volatile components were removed by a rotary pump (10 Pa) and a cold trap (dry ice + ethanol) to obtain 37.7 g of an organosilicon compound. Got.

In a 1 L four-necked eggplant flask, 37.7 g of the organosilicon compound obtained in a nitrogen atmosphere and 11.1 g of triethylamine were dissolved in 300 mL of toluene. To this solution, 17.0 g of phenoxyacetyl chloride was added dropwise over 30 minutes and stirred for 2 hours. Thereafter, the precipitate was filtered off and the solvent was removed by a rotary evaporator at 20 hPa / 40 ° C., and the organosilicon compound (C9-1) (C ₂₆ H ₄₇ NO ₅ SSi, molecular weight 513.81 represented by the following formula: 42.5 g of 3-phenoxyethanoylthio-propyl (decanoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane) was obtained.
¹ H-NMR (CDCl3, 700 MHz, δ; ppm) = 7.2 (t; 2H), 7.0 (t; 1H), 6.9 (d; 2H), 4.7 (s; 2H), 3.8 (q; 6H), 3.0 (t; 2H), 2.6 (t; 4H), 2.3 (s; 3H), 1.8 (m; 2H), 1.5 (m; 2H), 1.3 (m; 14H), 0.9 (t; 3H), 0.7 ( t; 2H)

<Production Example 10-1 of organosilicon compound>
In a 500 mL four-necked eggplant flask, 23.8 g of 3-mercapto-propyltriethoxysilane, 11.9 g of N-methyldiethanolamine, and 0.05 g of titanium tetra-n-butoxide were dissolved in 200 mL of xylene under a nitrogen atmosphere. The temperature was raised to 150 ° C. and stirred for 6 hours. Subsequently, 16.2 g of 2- (2-butoxyethoxy) ethanol was added dropwise and stirred for 2 hours. Thereafter, the solvent was removed by a rotary evaporator at 20 hPa / 40 ° C., and then the remaining volatile components were removed by a rotary pump (10 Pa) and a cold trap (dry ice + ethanol) to obtain 38.0 g of an organosilicon compound. Got.

In a 1 L four-necked eggplant flask, 38.0 g of the organosilicon compound and 11.1 g of triethylamine obtained in a nitrogen atmosphere were dissolved in 300 mL of toluene. To this solution, 17.0 g of phenoxyacetyl chloride was added dropwise over 30 minutes and stirred for 2 hours. Thereafter, the precipitate was filtered off and the solvent was removed by a rotary evaporator at 20 hPa / 40 ° C., and the organosilicon compound (C10-1) (C ₂₄ H ₄₁ NO ₇ SSi, molecular weight 515.74 represented by the following formula: 42.6 g of 3-phenoxyethanoylthio-propyl (2- (2-butoxyethoxy) ethoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane) was obtained.
¹ H-NMR (CDCl3, 700 MHz, δ; ppm) = 7.2 (t; 2H), 7.0 (t; 1H), 6.9 (d; 2H), 4.7 (s; 2H), 3.8 (m; 6H), 3.5 (m; 8H), 3.0 (t; 2H), 2.6 (t; 4H), 2.3 (s; 3H), 1.8 (m; 2H), 1.5 (m; 2H), 1.3 (m; 2H), 0.9 ( t; 3H), 0.7 (t; 2H)

<Production Example 11-1 of Organosilicon Compound>
Under a nitrogen atmosphere, 16.2 g of 2- (2-butoxyethoxy) ethanol and 0.05 g of p-toluenesulfonic acid were dissolved in 37.2 g of 3-phenoxyethanoylthio-propyltriethoxysilane in a 200 mL four-necked eggplant flask. The temperature was raised to 150 ° C. and stirred for 6 hours. Thereafter, the remaining volatile components were removed with a rotary pump (10 Pa) and a cold trap (dry ice + ethanol), and an organosilicon compound (C11-1) (C ₂₃ H ₄₀ O ₇ SSi represented by the following formula: 45.0 g of a molecular weight of 488.71, 3-phenoxyethanoylthio-propyl (2- (2-butoxyethoxy) ethoxy) diethoxysilane) was obtained.
¹ H-NMR (CDCl3, 700 MHz, δ; ppm) = 7.2 (t; 2H), 7.0 (t; 1H), 6.9 (d; 2H), 4.7 (s; 2H), 3.8 (m; 6H), 3.5 (m; 8H), 3.0 (t; 2H), 1.8 (m; 2H), 1.5 (m; 2H), 1.3 (m; 2H), 1.2 (t; 6H), 0.9 (t; 3H), 0.7 ( t; 2H)

<Preparation and evaluation of rubber composition>
The rubber composition of the mixing | blending prescription according to Tables 1-6 was knead | mixed and prepared with the Banbury mixer. Next, the vulcanization physical property of the obtained rubber composition was measured by the following method. The results are shown in Tables 1-6.

(1) Dynamic viscoelasticity Using a spectrometer (dynamic viscoelasticity measuring machine) manufactured by Ueshima Seisakusho, tan δ of vulcanized rubber at a frequency of 52 Hz, initial strain of 10%, measurement temperature of 60 ° C, and dynamic strain of 1%. In Tables 1-3, the value of tan δ of Comparative Example 1-1 was displayed as an index as 100. In Table 4, the value of tan δ of Comparative Example 6-1 was displayed as an index, and in Table 5, comparison was made. The value of tan δ in Example 8-1 was expressed as 100, and in Table 6, the value of tan δ in Comparative Example 10-1 was displayed as 100. The smaller the index value, the lower the tan δ, indicating that the rubber composition is less exothermic.

(2) Abrasion resistance test In accordance with JIS K 6264-2: 2005, a test was carried out under the conditions of room temperature and slip rate of 25% using a Lambone type abrasion tester. In Table 4, the reciprocal of the wear amount of 100 is displayed as an index. In Table 4, the reciprocal of the wear amount of Comparative Example 6-1 is displayed as an index. In Table 5, the reciprocal of the wear amount of Comparative Example 8-1 is displayed as 100. In Table 6, the reciprocal of the amount of wear in Comparative Example 10-1 is taken as 100 and displayed as an index. The larger the index value, the smaller the wear amount and the better the wear resistance.

* 1 JSR emulsion polymerization SBR, # 1500
* 2 Asahi Carbon # 80
* 3 Made by Tosoh Silica Industry Co., Ltd., nip seal AQ, BET surface area 220m ² / g
* 4 Bis (3-triethoxysilylpropyl) disulfide
* 5 Nouchi 6C, manufactured by Ouchi Shinsei Chemical Industry
* 6 Nouchi 224, manufactured by Ouchi Shinsei Chemical Industry
* 7 Sanshin Chemical Industry, Sunseller D
* 8 Sanshin Chemical Industries, Sunseller DM
* 9 Sunseller NS, manufactured by Sanshin Chemical Industry
* 11 2-Octanoylthio-propyltriethoxysilane

* 2, * 3, * 5, * 6, * 7, * 8, * 9, * 11 are the same as Tables 1-3
* 10 ESR emulsion polymerization SBR, # 1712 37.5 parts by weight of aromatic oil for 100 parts by weight of rubber component

* 1, * 3, * 4, * 5, * 6, * 7, * 8, * 11 are the same as Tables 1-4
* 12 JSR, RSS # 3
* 13 Asahi Carbon, # 78
* 14 N-cyclohexylbenzothiazole-2-sulfenamide

* 1, * 3, * 4, * 5, * 6, * 7, * 8, * 11, * 13 are the same as Tables 1-5
* 15 Made by Ouchi Shinsei Chemical Industry, Noxeller TOT-N

  According to Tables 1-6, it replaces with the conventional silane coupling agent (silane compound-1 and silane compound-2), and the organosilicon compounds (C1-1)-(C1-11) in the first aspect of the present invention. It can be seen that blending can significantly reduce the tan δ of the rubber composition, that is, significantly reduce the hysteresis loss and achieve low heat build-up, while also significantly improving the wear resistance.

[Organic silicon compound in the second embodiment of the present invention]
<Production Example 1-2 of organosilicon compound>
In a 1 L four-necked eggplant flask, 23.8 g of 3-mercaptopropyltriethoxysilane and 11.1 g of triethylamine were dissolved in 300 mL of toluene under a nitrogen atmosphere. To this solution, 12.2 g of methyl chloroglyoxylate was added dropwise over 30 minutes and stirred for 2 hours. Thereafter, the precipitate was filtered off and the solvent was removed by a rotary evaporator at 20 hPa / 40 ° C., and an organosilicon compound (C1-2) (C ₁₂ H ₂₄ O ₆ SSi, molecular weight 324.47, represented by the following formula: 30.5 g of 3-methyloxalylthio-propyltriethoxysilane) was obtained.
¹ H-NMR (CDCl3, 700 MHz, δ; ppm) = 3.8 (m; 9H), 2.8 (t; 2H), 1.6 (m; 2H), 1.2 (t; 9H), 0.6 (t; 2H)

<Production Example 2-2 of Organosilicon Compound>
In a 1 L four-necked eggplant flask, 23.8 g of 3-mercaptopropyltriethoxysilane and 11.1 g of triethylamine were dissolved in 300 mL of toluene under a nitrogen atmosphere. To this solution, 13.6 g of ethyl chloroglyoxylate was added dropwise over 30 minutes and stirred for 2 hours. Thereafter, the precipitate was filtered off and the solvent was removed by a rotary evaporator at 20 hPa / 40 ° C., and an organosilicon compound (C2-2) (C ₁₃ H ₂₆ O ₆ SSi represented by the following formula: molecular weight 338.49, 32.0 g of 3-ethyloxalylthio-propyltriethoxysilane) was obtained.
¹ H-NMR (CDCl3, 700 MHz, δ; ppm) = 4.3 (m; 2H), 3.8 (m; 6H), 2.8 (t; 2H), 1.6 (m; 2H), 1.3 (t; 3H), 1.2 (t; 9H), 0.6 (t; 2H)

<Production Example 3-2 of organosilicon compound>
In a 500 mL four-necked eggplant flask, 33.8 g of 3-ethyloxalylthio-propyltriethoxysilane, 11.9 g of N-methyldiethanolamine, and 0.05 g of titanium tetra-n-butoxide were dissolved in 200 mL of xylene under a nitrogen atmosphere. The temperature was raised to 150 ° C. and stirred for 6 hours. Then, the solvent was removed with a rotary evaporator at 20 hPa / 40 ° C, and then the remaining volatile components were removed with a rotary pump (10 Pa) and a cold trap (dry ice + ethanol). 34.0 g of an organosilicon compound (C3-2) (C ₁₄ H ₂₇ NO ₆ SSi, molecular weight 365.52, 3-ethyloxalylthio-propyl (ethoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane) Obtained.
^{1 H-NMR (CDCl3, 700MHz} , δ; ppm) = 4.3 (m; 2H), 3.8 (m; 6H), 2.8 (t; 2H), 2.5 (m; 4H), 2.4 (m; 3H), 1.6 (m; 2H), 1.3 (t; 3H), 1.2 (t; 3H), 0.6 (t; 2H)

<Production Example 4-2 of Organosilicon Compound>
In a 500 mL four-necked eggplant flask, 33.8 g of 3-ethyloxalylthio-propyltriethoxysilane, 27.3 g of N-lauryldiethanolamine, and 0.05 g of titanium tetra-n-butoxide were dissolved in 200 mL of xylene in a nitrogen atmosphere. The temperature was raised to 150 ° C. and stirred for 6 hours. Then, the solvent was removed with a rotary evaporator at 20 hPa / 40 ° C, and then the remaining volatile components were removed with a rotary pump (10 Pa) and a cold trap (dry ice + ethanol). that the organosilicon compound (C4-2) - a _{(C 25 H 49 NO 6 SSi} , molecular weight 519.81,3- ethyloxalyl thio propyl (ethoxy) 1,3-dioxa-6-dodecylaza-2-silacyclooctane) 49.1 g Obtained.
¹ H-NMR (CDCl3, 700 MHz, δ; ppm) = 4.3 (m; 2H), 3.8 (m; 6H), 2.8 (t; 2H), 2.5 (m; 4H), 2.4 (m; 2H), 1.6 (m; 2H), 1.4 (m; 2H), 1.3 (m; 21H), 1.2 (t; 3H), 0.9 (t; 3H), 0.6 (t; 2H)

<Production Example 5-2 of Organosilicon Compound>
In a 500 mL four-necked eggplant flask, 33.8 g of 3-ethyloxalylthio-propyltriethoxysilane, 11.9 g of N-methyldiethanolamine, and 0.05 g of titanium tetra-n-butoxide were dissolved in 200 mL of xylene under a nitrogen atmosphere. The temperature was raised to 150 ° C. and stirred for 6 hours. Subsequently, 15.8 g of decyl alcohol was added dropwise and stirred for 2 hours. Then, the solvent was removed with a rotary evaporator at 20 hPa / 40 ° C, and then the remaining volatile components were removed with a rotary pump (10 Pa) and a cold trap (dry ice + ethanol). 43.2 g of organic silicon compound (C5-2) (C ₂₂ H ₄₃ NO ₆ SSi, molecular weight 477.73, 3-ethyloxalylthio-propyl (decanoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane) Obtained.
¹ H-NMR (CDCl3, 700 MHz, δ; ppm) = 4.3 (m; 2H), 3.8 (m; 6H), 2.8 (t; 2H), 2.5 (m; 4H), 2.4 (m; 2H), 1.6 (m; 2H), 1.5 (m; 2H), 1.4 (m; 2H), 1.3 (m; 35H), 0.9 (t; 6H), 0.6 (t; 2H)

<Production Example 6-2 of Organosilicon Compound>
In a 500 mL four-necked eggplant flask, 33.8 g of 3-ethyloxalylthio-propyltriethoxysilane, 11.9 g of N-methyldiethanolamine, and 0.05 g of titanium tetra-n-butoxide were dissolved in 200 mL of xylene under a nitrogen atmosphere. The temperature was raised to 150 ° C. and stirred for 6 hours. Subsequently, 16.2 g of 2- (2-butoxyethoxy) ethanol was added dropwise and stirred for 2 hours. Then, the solvent was removed with a rotary evaporator at 20 hPa / 40 ° C, and then the remaining volatile components were removed with a rotary pump (10 Pa) and a cold trap (dry ice + ethanol). that the organosilicon compound _{(C6-2) (C 18 H 35} NO 8 SSi, molecular weight 453.62,3- ethyloxalyl thio - propyl (2- (2-butoxyethoxy) ethoxy) 1,3-dioxa-6-Mechiruaza -2 43.4 g of (silacyclooctane) was obtained.
^{1 H-NMR (CDCl3, 700MHz} , δ; ppm) = 4.3 (m; 2H), 3.8 (m; 6H), 3.5 (m; 8H), 2.8 (t; 2H), 2.5 (m; 4H), 2.4 (m; 2H), 1.6 (m; 2H), 1.5 (m; 2H), 1.4 (m; 2H), 1.3 (m; 23H), 0.9 (t; 6H), 0.6 (t; 2H)

<Production Example 7-2 of organosilicon compound>
In a 1 L four-necked eggplant flask, 18.0 g of 3-mercaptopropyldimethoxymethylsilane and 11.1 g of triethylamine were dissolved in 300 mL of toluene under a nitrogen atmosphere. To this solution, 13.6 g of ethyl chloroglyoxylate was added dropwise over 30 minutes and stirred for 2 hours. Thereafter, the precipitate was separated by filtration and the solvent was removed by a rotary evaporator at 20 hPa / 40 ° C. to obtain 26.2 g of 3-ethyloxalylthio-propyldimethoxymethylsilane.

Subsequently, 26.2 g of 3-ethyloxalylthio-propyldimethoxymethylsilane, 11.2 g of N-methyldiethanolamine, and 0.05 g of titanium tetra-n-butoxide were dissolved in 200 mL of xylene in a 500 mL four-necked eggplant flask. The temperature was raised to 150 ° C. and stirred for 2 hours. Then, the solvent was removed with a rotary evaporator at 20 hPa / 40 ° C, and then the remaining volatile components were removed with a rotary pump (10 Pa) and a cold trap (dry ice + ethanol). 27.5 g of an organosilicon compound (C7-2) (C ₁₃ H ₂₅ NO ₅ SSi, molecular weight 335.49, ₃ -ethyloxalylthio-propyl (methyl) 1,3-dioxa-6-methylaza-2-silacyclooctane) Obtained.
¹ H-NMR (CDCl3, 700 MHz, δ; ppm) = 4.3 (m; 2H), 3.8 (m; 4H), 2.8 (t; 2H), 2.5 (m; 4H), 2.4 (m; 3H), 1.6 (m; 2H), 1.3 (t; 3H), 0.6 (t; 2H), 0.1 (t; 3H)

<Production Example 8-2 of organosilicon compound>
In a 500 mL four-necked eggplant flask, 33.8 g of 3-ethyloxalylthio-propyltriethoxysilane, 17.8 g of dimethylethanolamine and 0.05 g of titanium tetra-n-butoxide were dissolved in 200 mL of xylene under a nitrogen atmosphere. The temperature was raised to 150 ° C. and stirred for 6 hours. Then, the solvent was removed with a rotary evaporator at 20 hPa / 40 ° C, and then the remaining volatile components were removed with a rotary pump (10 Pa) and a cold trap (dry ice + ethanol). 38.0 g of an organosilicon compound (C8-2) (C ₁₇ H ₃₆ N ₂ O ₆ SSi, molecular weight 424.63, 3-ethyloxalylthio-propyl (didimethylaminoethoxy) ethoxysilane) was obtained.
^{1 H-NMR (CDCl3, 700MHz} , δ; ppm) = 4.3 (m; 2H), 3.8 (m; 6H), 2.8 (t; 2H), 2.5 (m; 4H), 2.4 (m; 12H), 1.6 (m; 2H), 1.3 (t; 3H), 1.2 (t; 3H), 0.6 (t; 2H)

<Production Example 9-2 of organosilicon compound>
In a 500 mL four-necked eggplant flask, 33.8 g of 3-ethyloxalylthio-propyltriethoxysilane, 34.6 g of dibutylethanolamine and 0.05 g of titanium tetra-n-butoxide were dissolved in 200 mL of xylene under a nitrogen atmosphere. The temperature was raised to 150 ° C. and stirred for 6 hours. Then, the solvent was removed with a rotary evaporator at 20 hPa / 40 ° C, and then the remaining volatile components were removed with a rotary pump (10 Pa) and a cold trap (dry ice + ethanol). 50.0 g of an organosilicon compound (C9-2) (C ₂₉ H ₆₀ N ₂ O ₆ SSi, molecular weight 592.95, 3-ethyloxalylthio-propyl (didibutylaminoethoxy) ethoxysilane) was obtained.
¹ H-NMR (CDCl3, 700 MHz, δ; ppm) = 4.3 (m; 2H), 3.8 (m; 6H), 2.8 (t; 2H), 2.5 (m; 4H), 2.4 (m; 8H), 1.6 (m; 2H), 1.4 (m; 8H), 1.3 (m; 11H), 1.2 (t; 3H), 0.9 (t; 12H), 0.6 (t; 2H)

<Preparation and evaluation of rubber composition>
The rubber composition of the compounding prescription according to Tables 7-12 was knead | mixed and prepared with the Banbury mixer. Next, the vulcanization physical property of the obtained rubber composition was measured by the following method. The results are shown in Tables 7-12.

(1) Dynamic viscoelasticity Using a spectrometer (dynamic viscoelasticity measuring machine) manufactured by Ueshima Seisakusho, tan δ of vulcanized rubber at a frequency of 52 Hz, initial strain of 10%, measurement temperature of 60 ° C, and dynamic strain of 1%. In Tables 7 to 9, the value of tan δ of Comparative Example 1 is shown as an index with 100, in Table 10, the value of tan δ of Comparative Example 6-2 is shown as an index, and in Table 11, Comparative Example 8 is shown. The tan δ value of −2 is represented as an index of 100, and in Table 12, the tan δ value of Comparative Example 10-2 is represented as an index of 100. The smaller the index value, the lower the tan δ, indicating that the rubber composition is less exothermic.

(2) Abrasion resistance test In accordance with JIS K 6264-2: 2005, a test was performed at room temperature and a slip rate of 25% using a Lambourn type abrasion tester. The reciprocal of the amount of wear is shown as an index, and in Table 10, the reciprocal of the amount of wear in Comparative Example 6-2 is shown as an index, and in Table 11, the reciprocal of the amount of wear in Comparative Example 8-2 is shown as 100. In Table 12, the reciprocal of the amount of wear in Comparative Example 10-2 was taken as 100 and displayed as an index. The larger the index value, the smaller the wear amount and the better the wear resistance.

* 1 JSR emulsion polymerization SBR, # 1500
* 2 Asahi Carbon # 80
* 3 Made by Tosoh Silica Industry Co., Ltd., nip seal AQ, BET surface area 220m ² / g
* 4 Bis (3-triethoxysilylpropyl) disulfide
* 5 Nouchi 6C, manufactured by Ouchi Shinsei Chemical Industry
* 6 Nouchi 224, manufactured by Ouchi Shinsei Chemical Industry
* 7 Sanshin Chemical Industry, Sunseller D
* 8 Sanshin Chemical Industries, Sunseller DM
* 9 Sunseller NS, manufactured by Sanshin Chemical Industry
* 11 2-Octanoylthio-propyltriethoxysilane

* 2, * 3, * 5, * 6, * 7, * 8, * 9, * 11 are the same as Tables 7-9
* 10 ESR emulsion polymerization SBR, # 1712 37.5 parts by weight of aromatic oil for 100 parts by weight of rubber component

* 1, * 3, * 4, * 5, * 6, * 7, * 8, * 11 are the same as Tables 7-10
* 12 JSR, RSS # 3
* 13 Asahi Carbon, # 78
* 14 N-cyclohexylbenzothiazole-2-sulfenamide

* 1, * 3, * 4, * 5, * 6, * 7, * 8, * 11, * 13 are the same as Tables 7-11
* 15 Made by Ouchi Shinsei Chemical Industry, Noxeller TOT-N

  According to Tables 7-12, it replaces with the conventional silane coupling agent (silane compound-1 and silane compound-2), and the organosilicon compound (C2-1)-(C2-9) in the 2nd aspect of this invention. It can be seen that blending can significantly reduce the tan δ of the rubber composition, that is, significantly reduce the hysteresis loss and achieve low heat build-up, while also significantly improving the wear resistance.

Claims (17)

  An organosilicon compound having, in its molecule, a silicon atom to which at least one substituent that reacts with silica is bonded, and a sulfur atom to which a substituent including an electron withdrawing group is bonded.   The organosilicon compound according to claim 1, wherein the substituent that reacts with silica is a group containing an oxygen atom directly bonded to a silicon atom. The following general formula (I):

[In the formula (I), at least one of R ¹ , R ² and R ³ is the following general formula (II) or formula (III):

(In Formula (II) and Formula (III), M is —O— or —CH ₂ —, X and Y are each independently —O—, —NR ⁸ — or —CH ₂ —, and R ⁶ is -OR ^8, in -NR ⁸ R ⁹ or -R ^8, R ⁷ is ^{-NR 8 R 9, -NR 8 -NR} 8 R 9, in -N = NR ⁸ or H, provided that, R ⁸ is -C _n H _{2n + 1} , R ⁹ is —C _q H _{2q + 1} , and each of l, m, n and q is independently 0 to 20).
Others -M-C _l H _{2l + 1} or _{-M-C l H 2l-1} ( where, M and l have the same meanings as mentioned above), or _{- (M-C l H 2l} ) y C s H _{2s + 1} (M and l are as defined above, y and s are each independently 1 to 20), provided that one or more of R ¹ , R ² and R ³ is M − O-
R ⁴ represents the following general formula (IV) or formula (V):

(In formula (IV) and formula (V), M, X, Y, R ⁶ , l and m are as defined above, and R ¹⁰ is —NR ⁸ —, —NR ⁸ —NR ⁸ — or —N═. N-, wherein R ⁸ is as defined above) or -M-C ₁ H _2l — (wherein M and l are as defined above),
A ¹ represents the following general formula (VI) or formula (VII):

(In the formula (VI) and formula (VII), R ⁵ is the general formula (II) or Formula (III) or -C _l H _2l -R ¹¹ (wherein, R ¹¹ is -NR ⁸ R ^9, -NR ⁸ —NR ⁸ R ⁹ , —N═NR ⁸ , —M—C _m H _{2m + 1} or —M—C _m H _2m−1 , or a hydrocarbon group having an aromatic ring having 6 to 20 carbon atoms. Wherein R ⁸ , R ⁹ , M, l and m are as defined above), and R ¹⁶ is _a saturated or unsaturated group represented by —C _a H _{2a + 1} or —C _a H _2a-1. A saturated hydrocarbon group, and R ¹⁷ is a saturated or unsaturated hydrocarbon group represented by —C _b C _{2b + 1} or —C _b H _2b-1 (provided that a and b are each independently 0-20),
In formula (VII), Z and Q are each independently O, S or NR ⁵ , wherein R ⁵ is as defined above.] 3. The organosilicon compound according to 1 or 2. The following general formula (VIII):

[In the formula (VIII), W is —NR ⁸ —, —O— or —CR ⁸ R ¹⁵ — (wherein R ¹⁵ is —R ⁹ or —C _m H _2m —R ⁷ , provided that R ⁷ Is —NR ⁸ R ⁹ , —NR ⁸ —NR ⁸ R ⁹ , —N═NR ⁸ or H, R ⁸ is —C _n H _{2n + 1} , R ⁹ is —C _q H _{2q + 1} , m, n and q are each independently 0 to 20),
R ¹² and R ¹³ are each independently represented by —M—C ₁ H _{2 1} — (wherein M is —O— or —CH ₂ —, and 1 is 0 to 20),
R ¹⁴ is _{-M-C l H 2l + 1} , -M-C l H 2l -R 7 ( wherein, M, R ⁷ and l have the same meanings as mentioned above), or _{- (M-C l H 2l} ) _y C _s H _{2s + 1} (M and l are as defined above, y and s are each independently 1 to 20), provided that one or more of R ¹² , R ¹³ and R ¹⁴ M is -O-
R ⁴ represents the following general formula (IV) or formula (V):

(In formula (IV) and formula (V), M, l and m are as defined above, X and Y are each independently —O—, —NR ⁸ — or —CH ₂ —, and R ⁶ is in -OR ^8, -NR ⁸ R ⁹ or -R ^8, R ¹⁰ is ^{-NR 8 -, - NR 8 -NR} 8 - or -N = N-a, provided that, R ⁸ and R ⁹ is as defined above Or -M-C _l H _2l- (wherein M and l are as defined above),
A ¹ represents the following general formula (VI) or formula (VII):

(In the formula (VI) and formula (VII), R ⁵ is the general formula (II) or Formula (III) or -C _l H _2l -R ¹¹ (wherein, R ¹¹ is -NR ⁸ R ^9, -NR ⁸ —NR ⁸ R ⁹ , —N═NR ⁸ , —M—C _m H _{2m + 1} or —M—C _m H _2m−1 , or a hydrocarbon group having an aromatic ring having 6 to 20 carbon atoms. Wherein R ⁸ , R ⁹ , M, l and m are as defined above), and R ¹⁶ is _a saturated or unsaturated group represented by —C _a H _{2a + 1} or —C _a H _2a-1. A saturated hydrocarbon group, and R ¹⁷ is a saturated or unsaturated hydrocarbon group represented by —C _b C _{2b + 1} or —C _b H _2b-1 (provided that a and b are each independently 0-20),
In formula (VII), Z and Q are each independently O, S or NR ⁵ , wherein R ⁵ is as defined above.] 3. The organosilicon compound according to 1 or 2.   The organosilicon compound according to claim 3 or 4, wherein M is -O-. At least one of R ¹ , R ^2, and R ³ is represented by —O—C ₁ H _{2 l} —R ⁷ (where R ⁷ and l are as defined above), and the others are —O—C _1. H _{2l + 1} (where l is as defined above),
R ⁴ is represented by —C ₁ H _2l — (wherein l is as defined above),
Wherein R ⁵ (wherein, R ¹¹ and l have the same meanings as above) -C _l H _2l -R ¹¹ organosilicon compound according to claim 3, characterized by being represented by. Wherein R ^1, R ² and R ³ (wherein, R ^8, R ⁹ and l have the same meanings as mentioned above) at least one of ^{_{-O-C l H 2l -NR 8}} R 9 is represented by,
The R ⁵ is -C _l H _{2l + 1} (where l is as defined above) or a hydrocarbon group having an aromatic ring having 6 to 20 carbon atoms. The organosilicon compound described. W is represented by —NR ⁸ — (wherein R ⁸ is as defined above),
R ¹² and R ¹³ are each independently represented by —O—C ₁ H _2l — (wherein l is as defined above),
R ¹⁴ is represented by —O—C ₁ H _2l —R ⁷ (wherein R ⁷ and l are as defined above),
R ⁴ is represented by —C ₁ H _2l — (wherein l is as defined above),
The R ⁵ is —C _l H _{2l + 1} (where l is as defined above) or a hydrocarbon group having an aromatic ring having 6 to 20 carbon atoms. The organosilicon compound described. W is represented by —O— or —CR ⁸ R ⁹ — (wherein R ⁸ and R ⁹ are as defined above),
R ¹² and R ¹³ are each independently represented by —O—C ₁ H _2l — (wherein l is as defined above),
R ¹⁴ is represented by —O—C ₁ H _{2 1} —NR ⁸ R ⁹ (where R ⁸ , R ⁹ and l are as defined above),
R ⁴ is represented by —C ₁ H _2l — (wherein l is as defined above),
The organosilicon compound according to claim 4, wherein R ⁵ is represented by —C ₁ H _{2l + 1} (wherein l is as defined above).   An inorganic filler (B) and the organosilicon compound (C) according to any one of claims 1 to 9 are blended with a rubber component (A) made of natural rubber and / or a diene synthetic rubber. Rubber composition. To 100 parts by mass of the rubber component (A) composed of the natural rubber and / or diene synthetic rubber, 5 to 140 parts by mass of the inorganic filler (B)
Furthermore, 1-20 mass% of the compounding quantity of the said inorganic filler (B) is included for the said organosilicon compound (C), The rubber composition of Claim 10 characterized by the above-mentioned.   The rubber composition according to claim 10 or 11, wherein the inorganic filler (B) is silica or aluminum hydroxide. The rubber composition according to claim 12, wherein the silica has a BET surface area of 40 to 350 m ² / g.   A tire using the rubber composition according to claim 10.   The primer composition containing the organosilicon compound in any one of Claims 1-9.   The coating composition containing the organosilicon compound in any one of Claims 1-9.   The adhesive composition containing the organosilicon compound in any one of Claims 1-9.