JP5532471B2 - Method for producing cyclic sulfite ester - Google Patents

Description

  The present invention relates to a method for producing a cyclic sulfite ester useful for an electrolytic solution for a lithium battery or the like. More specifically, the present invention relates to a method for producing a cyclic sulfite ester using epoxide and sulfur dioxide as raw materials.

  Cyclic sulfites are compounds that are used in a wide range of applications such as acid generators, alkylating agents, and alkanesulfonic acid synthesis intermediates, and are particularly promising as electrolyte additives for lithium batteries and capacitors. Is being viewed.

  Traditionally, these cyclic sulfites have been produced by reacting the corresponding diol with thionyl chloride in the presence of a suitable base, but generally the yield is low and the salt of hydrogen chloride and base is large. By-products, and in some cases, a problematic method in that the product or the surrounding environment is contaminated with chlorine.

  As another method for obtaining a cyclic sulfite ester, a method is also known in which a corresponding epoxide and sulfur dioxide are reacted in the presence of a suitable homogeneous catalyst under suitable pressure conditions. Specifically, for example, a method using tetraethylammonium bromide as a homogeneous catalyst (for example, Patent Document 1, Non-Patent Document 1, etc.), tertiary amines such as tripropylamine and pyridine, tributylphosphine, triphenylphosphine, etc. A method using a phosphine catalyst (for example, Non-Patent Document 2) is known.

German Patent No. 1886610 J.Gen.Chem.USSR.31,1230 (1961) Makromol. Chem. 194, 2605 (1993)

  On the other hand, the present inventors have studied the production method of cyclic sulfites using epoxide and sulfur dioxide as raw materials as described above from the viewpoint of industrial scale production. In the conventional method using a homogeneous catalyst, if the reaction is carried out for a long time (when left), the yield of the cyclic sulfite ester, which is the target product, is significantly reduced due to decomposition of the product and the like. In order to suppress the decrease in the temperature, strict management of the reaction time is required, and it has been clarified that it has a problem that it is not suitable for industrial scale production. The present invention has been made in view of the above-described circumstances, and provides a cyclic sulfite ester that gives a cyclic sulfite ester with high yield and high selectivity and is advantageous for industrial-scale production that does not require strict time control. It is to provide a manufacturing method.

  That is, the industrial scale does not have the above-described problems, in other words, even if the reaction is carried out for a long time (even if left), the yield of the target cyclic sulfite ester is significantly reduced. As a result of extensive research on a method for producing a cyclic sulfite ester advantageous for production of the present invention, the present inventors have found that the above problems can be solved by performing a reaction using a catalyst supported on silica. It came to complete.

（式中、Ｒ^１及びＲ^２は夫々独立して、水素原子、ハロゲン原子が置換していてもよい炭素数１〜１０の直鎖状、分枝状若しくは環状のアルキル基又はハロゲン原子が置換していてもよいフェニル基を表すか、或いはＲ^１及びＲ^２はこれらが結合している炭素原子と共に、ハロゲン原子を置換基として有していてもよい炭素数５〜１０の環を形成するものを表す。）で示されるエポキシドと二酸化硫黄とを、第三級アミン性基又は第四級アンモニウムイオン性基で表面修飾されたシリカ触媒の存在下で反応させることを特徴とする、一般式（２）

（式中、Ｒ^１及びＲ^２は上記に同じ。）で示される環状亜硫酸エステルの製造方法の発明である。 The present invention relates to a general formula (1)

(Wherein R ¹ and R ² are each independently a hydrogen atom, a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms which may be substituted by a halogen atom, or a halogen atom. R ¹ and R ² together with the carbon atom to which they are bonded form a ring having 5 to 10 carbon atoms which may have a halogen atom as a substituent. The epoxide represented by formula (II) and sulfur dioxide are reacted in the presence of a silica catalyst surface-modified with a tertiary amine group or a quaternary ammonium ionic group. (2)

(Wherein R ¹ and R ² are the same as above).

  Moreover, the present invention comprises a silica surface-modified with a tertiary amine group or a quaternary ammonium ionic group, by reacting the epoxide represented by the general formula (1) with sulfur dioxide, It is an invention of a catalyst used when synthesizing the cyclic sulfite represented by the general formula (2).

  According to the production method of the present invention, when a cyclic sulfite is produced from epoxide and sulfur dioxide as raw materials, a catalyst supported on silica can be used to generate a reaction even if the reaction is carried out for a long time (even if left standing). The production of by-products due to decomposition of the product can be suppressed, and as a result, the yield can be increased at a high yield without causing a significant decrease in yield due to excessive reaction time or extreme variation in yield due to differences in reaction efficiency. It is possible to produce a cyclic sulfite ester. Furthermore, the present invention is an advantageous production method for industrial scale production from the viewpoint that a catalyst supported on silica is easier to recover and reuse than a homogeneous catalyst.

“In the linear, branched or cyclic alkyl group having 1 to 10 carbon atoms that may be substituted by a halogen atom” represented by R ¹ and R ² in the general formulas (1) and (2) Specific examples of the “halogen atom” include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and among them, a chlorine atom and a bromine atom are preferable.

“In the linear, branched or cyclic alkyl group having 1 to 10 carbon atoms that may be substituted by a halogen atom” represented by R ¹ and R ² in the general formulas (1) and (2) The “C1-C10 linear, branched or cyclic alkyl group” is not particularly limited as long as it is a C1-C10 linear, branched or cyclic alkyl group. For example, methyl group, ethyl group, n-propyl group, isopropyl group, cyclopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, cyclobutyl group, n-pentyl group, isopentyl group , Sec-pentyl group, tert-pentyl group, neopentyl group, 2-methylbutyl group, 1,2-dimethylpropyl group, 1-ethylpropyl group, cyclopentyl group, n-hexyl group, iso Xyl group, sec-hexyl group, tert-hexyl group, neohexyl group, 2-methylpentyl group, 1,2-dimethylbutyl group, 2,3-dimethylbutyl group, 1-ethylbutyl group, cyclohexyl group, n-heptyl group , Isoheptyl group, cycloheptyl group, n-octyl group, isooctyl group, sec-octyl group, tert-octyl group, cyclooctyl group, n-nonyl group, isononyl group, cyclononyl group, n-decyl group, isodecyl group, neodecyl group Group, cyclodecyl group, etc., among which a C1-C6 alkyl group is preferable, specifically, for example, methyl group, ethyl group, n-propyl group, isopropyl group, cyclopropyl group, n-butyl group, Isobutyl, sec-butyl, tert-butyl, cyclobutyl, n-pentyl, Sopentyl group, sec-pentyl group, tert-pentyl group, neopentyl group, 2-methylbutyl group, 1,2-dimethylpropyl group, 1-ethylpropyl group, cyclopentyl group, n-hexyl group, isohexyl group, sec-hexyl group , Tert-hexyl group, neohexyl group, 2-methylpentyl group, 1,2-dimethylbutyl group, 2,3-dimethylbutyl group, 1-ethylbutyl group, cyclohexyl group are preferable. A methyl group and an ethyl group which are alkyl groups are more preferable.

Specific examples of the “halogen atom” in the “phenyl group optionally substituted by a halogen atom” represented by R ¹ and R ² in the general formulas (1) and (2) include, for example, a fluorine atom, chlorine An atom, a bromine atom, an iodine atom, etc. are mentioned, A chlorine atom and a bromine atom are especially preferable.

In the general formulas (1) and (2), represented by R ¹ and R ² , together with the carbon atom to which they are bonded, forms a ring having 5 to 10 carbon atoms which may have a halogen atom as a substituent Specific examples of the “halogen atom” in “What to do” include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, and the like, and among them, a chlorine atom and a bromine atom are preferable.

In the general formulas (1) and (2), represented by R ¹ and R ² , together with the carbon atom to which they are bonded, forms a ring having 5 to 10 carbon atoms which may have a halogen atom as a substituent The “ring having 5 to 10 carbon atoms” is not particularly limited as long as it forms a cyclic structure having 5 to 10 carbon atoms. Specific examples include cyclopentane, cyclohexane, and cycloheptane. And cycloalkanes having 5 to 10 carbon atoms such as cyclooctane, cyclononane, and cyclodecane, cycloalkenes having 5 to 10 carbon atoms such as cyclopentene, cyclohexene, cycloheptene, cyclooctene, cyclononene, and cyclodecene. , Cycloheptane, cyclooctane, cyclononane, cyclodecane, etc. Cycloalkanes are preferred, among which even cyclopentane, cyclohexane, cycloheptane, cyclo alkanes having a carbon number of 5-8 cyclooctane and the like are more preferable.

As R ¹ and R ² in the general formulas (1) and (2), a hydrogen atom, a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms which may be substituted with a halogen atom is more preferable. preferable.

  Next, the production method of the present invention will be specifically described. In the present invention, the cyclic sulfite ester represented by the general formula (2), which is the target compound, comprises an epoxide represented by the general formula (1) and a predetermined amount of sulfur dioxide with respect to the epoxide. It can be produced by reacting in a solvent if necessary in the presence of a silica catalyst surface-modified with an amine group or a quaternary ammonium ionic group. In addition, the cyclic sulfite obtained here may be isolated and purified by a post-treatment operation described later after removing the silica catalyst.

（式中、Ｒ１’は水素原子又はメチル基を表す。）で示されるもの、すなわち、エチレンオキシド、プロピレンオキシドが好ましい。 As the epoxide represented by the general formula (1) used in the present invention, a commercially available product or a compound synthesized by a conventional method may be used as appropriate. Specifically, for example, ethylene oxide, propylene oxide, chloromethyl may be used. Ethylene oxide, butylene oxide, isobutylene oxide, pentylene oxide, hexylene oxide, heptylene oxide, octylene oxide, nonylene oxide, decylene oxide, undecylene oxide, dodecylene oxide, styrene oxide, chlorostyrene oxide, bromostyrene Oxides, cyclopentene oxides, cyclohexene oxides, chlorocyclohexene oxides, cyclohexadiene monooxides, and the like. However, the present invention is not limited to the compounds exemplified here, and is represented by the general formula (1). No problem if that epoxide. From the viewpoint of obtaining advantageous effects different from the effects of the present invention, such as easy isolation and purification of the cyclic sulfite ester, among the epoxides represented by the general formula (1), General formula (18) which can produce a cyclic sulfite which can be easily separated and purified

(Wherein R1 ′ represents a hydrogen atom or a methyl group), that is, ethylene oxide and propylene oxide are preferred.

（式中、Ｒ１’は上記に同じ。）で示されるもの、すなわち、エチレンスルフィット、プロピレンスルフィットが好ましい。 Specific examples of the cyclic sulfite ester represented by the general formula (2) produced in the present invention include, for example, ethylene sulfite, propylene sulfite, chloromethylethylene sulfite, butylenesulfite, isobutylenesulfite, and pentylenesulfite. , Hexylene sulfite, heptylene sulfite, octyl lenthru fit, nonirence sphere fit, decience sphere fit, undecyl sulfite, dodecyl sulfite, styrene sulfite, chlorostyrene sulfite, bromostyrene sulfite , Cyclopentene sulfite, cyclohexene sulfite, chlorocyclohexene sulfite, cyclohexadiene monosulfite, etc., but the present invention is limited to the compounds exemplified herein. , No problem if the cyclic sulfite of the formula (2). From the standpoint of obtaining advantageous effects different from the effects of the present invention, such as easy isolation and purification of cyclic sulfites, among the cyclic sulfites represented by the general formula (2). And general formula (19)

(Wherein R1 ′ is the same as above), that is, ethylene sulfite and propylene sulfite are preferable.

  The sulfur dioxide used in the present invention can be used without any problem as long as it is ordinary sulfur dioxide. The sulfur dioxide may be supplied as a gas by directly blowing it into the reaction system, or may be dissolved in a suitable solvent in advance. Any supply form of sulfur dioxide may be used, for example, by supplying the sulfur dioxide together with the solvent into the reaction system. The amount of sulfur dioxide used is not particularly limited, but is usually 0.5 molar equivalent to 10 molar equivalents, preferably 0.8 molar equivalents to 4 moles, relative to the number of moles of the epoxide represented by the general formula (1). Molar equivalent.

  The silica catalyst surface-modified with a tertiary amine group or quaternary ammonium ionic group used in the present invention has a tertiary amine group or quaternary ammonium ion as part of the silanol group in silica. Specifically, a halogen atom, a hydroxyl group, or an alkoxy group bonded to a silicon atom in a silicon-containing compound having a group derived from a tertiary amine or a group derived from a quaternary ammonium ion. Is obtained by reacting at least one reactive group such as a surface silanol group in silica with a condensation reaction such as dehydrohalogenation, dehydration, or dealcoholization. The silica catalyst usually has a tertiary amine group or a quaternary ammonium ionic group derived from the silicon-containing compound bonded to the silica by a chemical bond. .

｛式中、Ｒ^３は結合手、炭素数１〜８のアルキレン基、炭素数６〜１２のアリーレン基又は炭素数７〜１２のアラルキレン基を表し、Ｒ^４は夫々独立して、炭素数１〜８の直鎖状、分枝状若しくは環状のアルキル基、ハロゲン原子、水酸基、炭素数１〜８の直鎖状、分枝状若しくは環状のアルコキシ基又はアリル基を表し、Ｙは第三級アミン由来の基又は第四級アンモニウムイオン由来の基を表し、Ｚはハロゲン原子、水酸基、炭素数１〜８の直鎖状、分枝状若しくは環状のアルコキシ基、アリル基又は一般式（Ａ）

（式中、Ｒ^３、Ｒ^４及びＹは上記に同じ。）で示されるシラザン基を表す。｝で示される含ケイ素化合物とシリカとを反応させることにより得られるもので、シリカ中の表面シラノール基が、一般式（４）

（式中、Ｒ^３、Ｒ^４及びＹは上記に同じ。）で示される基、一般式（５）

（式中、Ｒ^３、Ｒ^４及びＹは上記に同じ。）で示される基、又は一般式（６）

（式中、Ｒ^３及びＹは上記に同じ。）で示される基で化学修飾されたもの、すなわち、シリカの表面に上記一般式（４）、（５）又は（６）で示されるものとなっている構成単位を有するものをいう。なお、ここでいう第四級アンモニウムイオン性基及び第四級アンモニウムイオン由来の基は、カウンターアニオンを有する第四級アンモニウム基を意味する。 More specifically, the silica catalyst surface-modified with the tertiary amine group or the quaternary ammonium ionic group has the general formula (3)

{In the formula, R ³ represents a bond, an alkylene group having 1 to 8 carbon atoms, an arylene group having 6 to 12 carbon atoms or an aralkylene group having 7 to 12 carbon atoms, and R ⁴ each independently represents 1 carbon atom. Represents a linear, branched or cyclic alkyl group of ˜8, a halogen atom, a hydroxyl group, a linear, branched or cyclic alkoxy group having 1 to 8 carbon atoms, or an allyl group, and Y is a tertiary group. Represents a group derived from an amine or a group derived from a quaternary ammonium ion, and Z represents a halogen atom, a hydroxyl group, a linear, branched or cyclic alkoxy group having 1 to 8 carbon atoms, an allyl group, or a general formula (A).

(Wherein R ³ , R ⁴ and Y are the same as above), a silazane group represented by } Is obtained by reacting a silicon-containing compound represented by the formula (4) with a surface silanol group in silica.

(Wherein R ³ , R ⁴ and Y are the same as above), a group represented by the general formula (5)

(Wherein R ³ , R ⁴ and Y are the same as above), or a group represented by the general formula (6)

(Wherein R ³ and Y are the same as above), ie, those chemically modified with a group represented by the above formula (4), (5) or (6) on the surface of silica Which has a structural unit. In addition, the quaternary ammonium ion group and the group derived from the quaternary ammonium ion mentioned here mean a quaternary ammonium group having a counter anion.

In the general formulas (3), (4), (5), (6) and (A), the alkylene group having 1 to 8 carbon atoms represented by R ³ is a linear or branched chain having 1 to 8 carbon atoms. The alkylene group is not particularly limited as long as it is a cyclic or cyclic alkylene group. Specifically, for example, a methylene group, a dimethylene group (ethylene group), a trimethylene group, a tetramethylene group, a pentamethylene group, a hexamethylene group, a heptamethylene group, an octane group, Methylene group, methylmethylene group, methyldimethylene group (methylethylene group), methyltrimethylene group, methyltetramethylene group, methylpentamethylene group, methylhexamethylene group, methylheptamethylene group, ethylmethylene group, ethyldimethylene group (Ethylethylene group), ethyltrimethylene group, ethyltetramethylene group, ethylpentamethylene group, ethylhexa Methylene group, propylmethylene group, propyldimethylene group (propylethylene group), propyltrimethylene group, propyltetramethylene group, propylpentamethylene group, butylmethylene group, butyldimethylene group (butylethylene group), butyltrimethylene group Butyltetramethylene group, pentylmethylene group, pentyldimethylene group (pentylethylene group), pentyltrimethylene group, hexylmethylene group, hexyldimethylene group (hexylethylene group), etc. A dimethylene group (ethylene group), trimethylene group and tetramethylene group which are linear alkylene groups are preferred. In addition, an alkyl group such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, or a hexyl group substituted on the alkylene chain may be bonded to any carbon of the alkylene chain, and these alkyl groups Is not limited to a linear n-form, and may be branched or cyclic such as an iso-form, a sec-form, and a tert-form.

In the general formulas (3), (4), (5), (6) and (A), the arylene group having 6 to 12 carbon atoms represented by R ³ may be monocyclic, condensed polycyclic, or ring assembly. Specifically, for example, a phenylene group, a naphthylene group, an azulylene group, a biphenylene group, and the like can be given.

In the general formulas (3), (4), (5), (6) and (A), the aralkylene group having 7 to 12 carbon atoms represented by R ³ includes a benzylene group, a phenethylene group and an α-methylbenzylene group. 3-phenylpropylene group, 1-methyl-1-phenylethylene group, 4-phenylbutylene group, 2-methyl-2-phenylpropylene group, 1,2,3,4-tetrahydronaphthylene group, naphthylmethylene group, Examples include 2-naphthylethylene group.

R ³ in general formulas (3), (4), (5), (6) and (A) is more preferably a bond or an alkylene group having 1 to 8 carbon atoms.

Specific examples of the linear, branched or cyclic alkyl group having 1 to 8 carbon atoms represented by R ⁴ in the general formulas (3), (4), (5) and (A) include, for example, Methyl group, ethyl group, n-propyl group, isopropyl group, cyclopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, cyclobutyl group, n-pentyl group, isopentyl group, sec-pentyl Group, tert-pentyl group, neopentyl group, 2-methylbutyl group, 1,2-dimethylpropyl group, 1-ethylpropyl group, cyclopentyl group, n-hexyl group, isohexyl group, sec-hexyl group, tert-hexyl group, Neohexyl group, 2-methylpentyl group, 1,2-dimethylbutyl group, 2,3-dimethylbutyl group, 1-ethylbutyl group, cyclohexyl Group, n-heptyl group, isoheptyl group, cycloheptyl group, n-octyl group, isooctyl group, sec-octyl group, tert-octyl group, cyclooctyl group and the like. Among them, an alkyl group having 1 to 6 carbon atoms. Specifically, for example, methyl group, ethyl group, n-propyl group, isopropyl group, cyclopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, cyclobutyl group, n- Pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, neopentyl group, 2-methylbutyl group, 1,2-dimethylpropyl group, 1-ethylpropyl group, cyclopentyl group, n-hexyl group, isohexyl group, sec -Hexyl group, tert-hexyl group, neohexyl group, 2-methylpentyl group, 1, - dimethylbutyl group, 2,3-dimethylbutyl group, 1-ethylbutyl group, a cyclohexyl group are preferably exemplified, and among them methyl group which is an alkyl group having 1 to 2 carbon atoms, an ethyl group are more preferable.

Specific examples of the halogen atom represented by R ⁴ in the general formulas (3), (4), (5) and (A) and Z in the general formula (3) include, for example, a fluorine atom, a chlorine atom, bromine An atom, an iodine atom, etc. are mentioned, A chlorine atom, a bromine atom, and an iodine atom are especially preferable.

A linear, branched or cyclic alkoxy group having 1 to 8 carbon atoms represented by R ⁴ in the general formulas (3), (4), (5) and (A) and Z in the general formula (3). Specifically, for example, methoxy group, ethoxy group, n-propoxy group, isopropoxy group, cyclopropoxy group, n-butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, cyclobutoxy group, n-pentyloxy group, isopentyloxy group, sec-pentyloxy group, tert-pentyloxy group, neopentyloxy group, 2-methylbutoxy group, 1,2-dimethylpropoxy group, 1-ethylpropoxy group, cyclopentyloxy Group, n-hexyloxy group, isohexyloxy group, sec-hexyloxy group, tert-hexyloxy group, ne Hexyloxy group, 2-methylpentyloxy group, 1,2-dimethylbutoxy group, 2,3-dimethylbutoxy group, 1-ethylbutoxy group, cyclohexyloxy group, n-heptyloxy group, isoheptyloxy group, cycloheptyl An oxy group, an n-octyloxy group, an isooctyloxy group, a sec-octyloxy group, a tert-octyloxy group, a cyclooctyloxy group, and the like. Among them, an alkoxy group having 1 to 6 carbon atoms is preferable. For example, methoxy group, ethoxy group, n-propoxy group, isopropoxy group, cyclopropoxy group, n-butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, cyclobutoxy group, n-pentyloxy group, Isopentyloxy group, sec-pentyloxy group, tert-pe Nyloxy group, neopentyloxy group, 2-methylbutoxy group, 1,2-dimethylpropoxy group, 1-ethylpropoxy group, cyclopentyloxy group, n-hexyloxy group, isohexyloxy group, sec-hexyloxy group, tert -Hexyloxy group, neohexyloxy group, 2-methylpentyloxy group, 1,2-dimethylbutoxy group, 2,3-dimethylbutoxy group, 1-ethylbutoxy group, cyclohexyloxy group are preferable, among which carbon A methoxy group and an ethoxy group that are alkoxy groups of 1 or 2 are more preferable.

R ⁴ in the general formulas (3), (4) and (5) is a linear, branched or cyclic alkyl group having 1 to 8 carbon atoms, a halogen atom, or a linear chain having 1 to 8 carbon atoms. A branched or cyclic alkoxy group is more preferable, and a linear, branched or cyclic alkoxy group having 1 to 8 carbon atoms is more preferable.

  Z in the general formula (3) is more preferably a halogen atom, a linear, branched or cyclic alkoxy group having 1 to 8 carbon atoms, or a silazane group represented by the above general formula (A). 1-8 linear, branched or cyclic alkoxy groups are more preferred.

（式中、Ｒ^５及びＲ^６は夫々独立して、炭素数１〜８の直鎖状、分枝状若しくは環状のアルキル基、炭素数６〜１０のアリール基又は炭素数７〜１２のアラルキル基を表す。）で示される非環式第三級アミノ基、一般式（８）

（式中、Ｒ^７は二重結合を有していてもよい炭素数４〜５のアルキレン基を表す。）で示される複素環式非芳香族第三級アミノ基、一般式（９）

（式中、Ｒ^８は二重結合を有する炭素数５〜９の４価の基を表す。）で示される複素環式芳香族第三級アミン由来の基、一般式（１０）

（式中、Ｒ^９は二重結合を有していてもよい炭素数４〜５の３価の基を表し、Ｒ^１０は炭素数１〜８の直鎖状、分枝状若しくは環状のアルキル基を表す。）で示される複素環式非芳香族第三級アミン由来の基等が挙げられ、また、第四級アンモニウムイオン由来の基の具体例としては、例えば一般式（１１）

（式中、Ｒ^１１、Ｒ^１２及びＲ^１３は夫々独立して、炭素数１〜８の直鎖状、分枝状若しくは環状のアルキル基、炭素数６〜１０のアリール基又は炭素数７〜１２のアラルキル基を表し、Ｘ⁻はカウンターアニオンを表す。）で示される非環式第四級アンモニオ基、一般式（１２）

（式中、Ｒ^１４は二重結合を有していてもよい炭素数４〜５のアルキレン基を表し、Ｒ^１５は炭素数１〜８の直鎖状、分枝状若しくは環状のアルキル基を表し、Ｘ⁻は上記に同じ。）で示される複素環式非芳香族第四級アンモニオ基、一般式（１３）

（式中、Ｒ^１６は二重結合を有する炭素数５〜９の３価の基を表し、Ｘ⁻は上記に同じ。）で示される複素環式芳香族第四級アンモニオ基、一般式（１４）

（式中、Ｒ^１７は二重結合を有していてもよい炭素数４〜５の３価の基を表し、Ｒ^１８及びＲ^１９は夫々独立して、炭素数１〜８の直鎖状、分枝状若しくは環状のアルキル基を表し、Ｘ⁻は上記に同じ。）で示される複素環式非芳香族第四級アンモニウムイオン由来の基、一般式（１５）

（式中、Ｒ^２０は二重結合を有する炭素数５〜９の４価の基を表し、Ｒ^２１は炭素数１〜８の直鎖状、分枝状若しくは環状のアルキル基を表し、Ｘ⁻は上記に同じ。）で示される複素環式芳香族第四級アンモニウムイオン由来の基等が挙げられる。 In the general formulas (3), (4), (5), (6) and (A), the group derived from the tertiary amine or the group derived from the quaternary ammonium ion represented by Y is the third in the formula. A monovalent group having a quaternary amine structure or a quaternary ammonium ion structure is represented. Specific examples of the tertiary amine-derived group include, for example, the general formula (7)

(In the formula, R ⁵ and R ⁶ are each independently a linear, branched or cyclic alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, or an aralkyl having 7 to 12 carbon atoms. Acyclic tertiary amino group represented by the general formula (8):

(Wherein R ⁷ represents an alkylene group having 4 to 5 carbon atoms which may have a double bond), a heterocyclic non-aromatic tertiary amino group represented by the general formula (9)

(Wherein R ⁸ represents a C 5-9 tetravalent group having a double bond), a group derived from a heterocyclic aromatic tertiary amine represented by the general formula (10)

(In the formula, R ⁹ represents a trivalent group having 4 to 5 carbon atoms which may have a double bond, and R ¹⁰ is a linear, branched or cyclic alkyl having 1 to 8 carbon atoms. A group derived from a heterocyclic non-aromatic tertiary amine represented by formula (11)), and specific examples of the group derived from a quaternary ammonium ion include, for example, the general formula (11)

(In the formula, R ¹¹ , R ¹² and R ¹³ are each independently a linear, branched or cyclic alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, or 7 to 7 carbon atoms. It represents a 12 aralkyl group, X ^-. acyclic quaternary ammonio group represented by representing a counter anion), the general formula (12)

(In the formula, R ¹⁴ represents an alkylene group having 4 to 5 carbon atoms which may have a double bond, and R ¹⁵ represents a linear, branched or cyclic alkyl group having 1 to 8 carbon atoms. It represents, X ^-. heterocyclic aromatic quaternary ammonio group represented by the same) in the general formula (13)

(Wherein R ¹⁶ represents a trivalent group having 5 to 9 carbon atoms having a double bond, and X ⁻ is the same as above), a heterocyclic aromatic quaternary ammonio group represented by the general formula ( 14)

(In the formula, R ¹⁷ represents a trivalent group having 4 to 5 carbon atoms which may have a double bond, and R ¹⁸ and R ¹⁹ are each independently a straight chain having 1 to 8 carbon atoms. Represents a branched or cyclic alkyl group, and X ⁻ is the same as defined above), a group derived from a heterocyclic non-aromatic quaternary ammonium ion represented by the general formula (15):

(Wherein R ²⁰ represents a tetravalent group having 5 to 9 carbon atoms having a double bond, R ²¹ represents a linear, branched or cyclic alkyl group having 1 to 8 carbon atoms; ^-. it is the same as that described above) heteroaromatic quaternary ammonium ions derived from group represented by may be mentioned.

R ⁵ , R ⁶ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ , R ¹⁵ , R ¹⁸ in the general formulas (7), (10), (11), (12), (14) and (15), Specific examples of the linear, branched or cyclic alkyl group having 1 to 8 carbon atoms represented by R ¹⁹ and R ²¹ include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a cyclo group. Propyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, cyclobutyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, neopentyl group, 2-methylbutyl group, 1,2-dimethylpropyl group, 1-ethylpropyl group, cyclopentyl group, n-hexyl group, isohexyl group, sec-hexyl group, tert-hexyl group, neohexyl 2-methylpentyl group, 1,2-dimethylbutyl group, 2,3-dimethylbutyl group, 1-ethylbutyl group, cyclohexyl group, n-heptyl group, isoheptyl group, cycloheptyl group, n-octyl group, isooctyl group , Sec-octyl group, tert-octyl group, cyclooctyl group, etc. Among them, an alkyl group having 1 to 6 carbon atoms is preferable, and specifically, for example, methyl group, ethyl group, n-propyl group, isopropyl group , Cyclopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, cyclobutyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, neopentyl group, 2-methylbutyl Group, 1,2-dimethylpropyl group, 1-ethylpropyl group, cyclopentyl group, n-he Sil group, isohexyl group, sec-hexyl group, tert-hexyl group, neohexyl group, 2-methylpentyl group, 1,2-dimethylbutyl group, 2,3-dimethylbutyl group, 1-ethylbutyl group, cyclohexyl group are preferable. Among them, an alkyl group having 1 to 4 carbon atoms is more preferable, and specifically, for example, methyl group, ethyl group, n-propyl group, isopropyl group, cyclopropyl group, n-butyl group, isobutyl group, sec -Butyl group, tert-butyl group, cyclobutyl group and the like are more preferable, among which a methyl group and an ethyl group which are alkyl groups having 1 to 2 carbon atoms are more preferable.

The aryl group having 6 to 10 carbon atoms represented by R ⁵ , R ⁶ , R ¹¹ , R ¹² and R ¹³ in the general formulas (7) and (11) may be either monocyclic or condensed polycyclic. Specific examples include a phenyl group, a naphthyl group, and an azulenyl group.

The aralkyl group having 7 to 12 carbon atoms represented by R ⁵ , R ⁶ , R ¹¹ , R ¹² and R ¹³ in the general formulas (7) and (11) may be monocyclic or condensed polycyclic. Specifically, for example, benzyl group, phenethyl group, α-methylbenzyl group, 3-phenylpropyl group, 1-methyl-1-phenylethyl group, 4-phenylbutyl group, 2-methyl-2- Examples include phenylpropyl group, 1,2,3,4-tetrahydronaphthyl group, naphthylmethyl group, 2-naphthylethyl group and the like.

As R < ⁵ >, R < ⁶ >, R <^11> , R < ¹² > and R < ¹³ > in General formula (7) and (11), a C1-C8 linear, branched or cyclic alkyl group is more preferable.

Specific examples of the alkylene group having 4 to 5 carbon atoms which may have a double bond represented by R ⁷ and R ¹⁴ in the general formulas (8) and (12) include, for example, a tetramethylene group and a pentane group. An alkylene group having 4 to 5 carbon atoms having no double bond such as a methylene group, but-1-ene-1,4-diyl group, but-2-ene-1,4-diyl group, buta-1, 3-diene-1,4-diyl group, penta-1-ene-1,5-diyl group, penta-2-ene-1,5-diyl group, penta-1,3-diene-1,5-diyl Group, an alkylene group having 4 to 5 carbon atoms (alkenylene group) having a double bond such as a penta-1,4-diene-1,5-diyl group.

Examples of the tetravalent group having 5 to 9 carbon atoms having a double bond represented by R ⁸ and R ²⁰ in the general formulas (9) and (15) include 3 to the nitrogen atom in the general formulas (9) and (15). Among the two bonds, as a name when the carbon atom substituted with a bond that forms a double bond with a nitrogen atom is defined as the 1st position, specifically, for example, penta-1,2,4-triene- 1,1,1,5-tetrayl group, penta-1,2,4-triene-1,1,2,5-tetrayl group, penta-1,2,4-triene-1,1,3,5- Tetravalent group having 5 carbon atoms such as tetrayl group, benzo [b] penta-1,2,4-triene-1,1,1,5-tetrayl group, benzo [b] penta-1,2,4- Triene-1,1,4,5-tetrayl group, benzo [b] penta-1,2,4-triene- , 1,5,5-tetrayl group, benzo [b] penta-1,2,4-triene-1,1,1 ′, 5-tetrayl group, benzo [b] penta-1,2,4-triene- 1,1,2 ′, 5-tetrayl group, benzo [b] penta-1,2,4-triene-1,1,3 ′, 5-tetrayl group, benzo [b] penta-1,2,4- Triene-1,1,4 ′, 5-tetrayl group, benzo [d] penta-1,2,4-triene-1,1,1,5-tetrayl group, benzo [d] penta-1,2,4 -Triene-1,1,2,5-tetrayl group, benzo [d] penta-1,2,4-triene-1,1,3,5-tetrayl group, benzo [d] penta-1,2,4 -Triene-1,1,1 ', 5-tetrayl group, benzo [d] penta-1,2,4-triene-1,1,2', 5- Tetrayl group, benzo [d] penta-1,2,4-triene-1,1,3 ′, 5-tetrayl group, benzo [d] penta-1,2,4-triene-1,1,4 ′, Examples thereof include a tetravalent group having 9 carbon atoms such as a 5-tetrayl group.

Examples of the trivalent group having 4 to 5 carbon atoms which may have a double bond represented by R ⁹ and R ¹⁷ in general formulas (10) and (14) include general formulas (10) and (14) As the nomenclature when the carbon atom substituted by any one of the two bonds to the nitrogen atom in 1 is taken as the 1st position, specifically, for example, tetramethyl-1,1,4-triyl Double group such as tetramethyl-1,2,4-triyl group, pentamethyl-1,1,5-triyl group, pentamethyl-1,2,5-triyl group, pentamethyl-1,3,5-triyl group A trivalent group having 4 to 5 carbon atoms having no bond, but-1-ene-1,1,4-triyl group, but-1-ene-1,2,4-triyl group, but-1- Ene-1,3,4-triyl group, but-1-ene-1,4,4-triyl , But-2-ene-1,1,4-triyl group, but-2-ene-1,2,4-triyl group, buta-1,3-diene-1,1,4-triyl group, butane 1,3-diene-1,2,4-triyl group, penta-1-ene-1,1,5-triyl group, penta-1-ene-1,2,5-triyl group, penta-1-ene -1,3,5-triyl group, penta-1-ene-1,4,5-triyl group, penta-1-ene-1,5,5-triyl group, penta-2-ene-1,1, 5-triyl group, penta-2-ene-1,2,5-triyl group, penta-2-ene-1,3,5-triyl group, penta-2-ene-1,4,5-triyl group, Penta-2-ene-1,5,5-triyl group, penta-1,3-diene-1,1,5-triyl group, penta-1,3-diene- 1,2,5-triyl group, penta-1,3-diene-1,3,5-triyl group, penta-1,3-diene-1,4,5-triyl group, penta-1,3-diene -1,5,5-triyl group, penta-1,4-diene-1,1,5-triyl group, penta-1,4-diene-1,2,5-triyl group, penta-1,4- Examples thereof include a trivalent group having 4 to 5 carbon atoms having a double bond such as a diene-1,3,5-triyl group.

The trivalent group having 5 to 9 carbon atoms having a double bond represented by R ¹⁶ in the general formula (13) includes a nitrogen atom and a double bond among the three bonds to the nitrogen atom in the general formula (13). As the nomenclature when the carbon atom substituted with the bond forming the bond is defined as the 1st position, specifically, for example, carbon such as penta-1,2,4-triene-1,1,5-triyl group A trivalent group of formula 5, benzo [b] penta-1,2,4-triene-1,1,5-triyl group, benzo [d] penta-1,2,4-triene-1,1,5 -A trivalent group having 9 carbon atoms, such as a triyl group.

Examples of the counter anion represented by X ⁻ in the general formulas (11), (12), (13), (14) and (15) include halide ions, carbonate ions, nitrate ions, sulfate ions, phosphate ions, Carboxylate ions such as borate ion, formate ion, acetate ion, organic acid ions such as sulfonate ion such as trifluoromethanesulfonate ion, p-toluenesulfonate ion, mono- or dialkylphosphate ion, mono- or dialkylborate Among these counter anions, halide ions are preferred, and specific examples of the halide ions include fluoride ions, chloride ions, bromide ions, iodide ions and the like. Of these, chloride ions, bromide ions, and iodide ions are preferred. Yes.

  Specific examples of the acyclic tertiary amino group represented by the general formula (7) include, for example, a dimethylamino group, a diethylamino group, an ethylmethylamino group, a methylpropylamino group, an ethylpropylamino group, a dipropylamino group, Butylmethylamino, butylethylamino, butylpropylamino, dibutylamino, methylpentylamino, ethylpentylamino, pentylpropylamino, butylpentylamino, dipentylamino, hexylmethylamino, ethylhexylamino Group, hexylpropylamino group, butylhexylamino group, hexylpentylamino group, dihexylamino group, diheptylamino group, dioctylamino group, methylphenylamino group, ethylphenylamino group, diphenylamino group, methylnaphthylamino Group, ethylnaphthylamino group, naphthylphenylamino group, dinaphthylamino group, benzylmethylamino group, benzylethylamino group, phenylbenzylamino group, dibenzylamino group, methylphenethylamino group, ethylphenethylamino group, phenylphenethylamino group Group, benzylphenethylamino group, diphenethylamino group and the like, but are not necessarily limited to the groups exemplified here, and any non-cyclic tertiary amino group represented by the general formula (7) may be used. . The alkyl groups such as propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group and the like exemplified here are not limited to linear n-forms, but are isoforms, sec-forms, tert-forms. It may be branched or cyclic like a body.

  Specific examples of the heterocyclic non-aromatic tertiary amino group represented by the general formula (8) include, for example, 1-pyrrolidino group, 1-piperidino group, 1-pyrrolyl group, 2,3-dihydro-1H-1 -Pyrrolyl group, 2,5-dihydro-1H-1-pyrrolyl group, 1,2,3,4-tetrahydro-1-pyridyl group, 1,2,5,6-tetrahydro-1-pyridyl group, 1,2 -Dihydro-1-pyridyl group, 1H, 3H-1-pyridyl group and the like can be mentioned.

  Specific examples of the group derived from the heterocyclic aromatic tertiary amine represented by the general formula (9) include, for example, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 2-quinolyl group, and 3-quinolyl. Group, 4-quinolyl group, 5-quinolyl group, 6-quinolyl group, 7-quinolyl group, 8-quinolyl group, 1-isoquinolyl group, 3-isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group Group, 7-isoquinolyl group, 8-isoquinolyl group and the like, but is not necessarily limited to the groups exemplified here, and is a group derived from a heterocyclic aromatic tertiary amine represented by the general formula (9). There is no problem if there is.

  Specific examples of the group derived from the heterocyclic non-aromatic tertiary amine represented by the general formula (10) include N-methyl-2-pyrrolidinyl group, N-ethyl-2-pyrrolidinyl group, N-propyl- 2-pyrrolidinyl group, N-butyl-2-pyrrolidinyl group, N-pentyl-2-pyrrolidinyl group, N-hexyl-2-pyrrolidinyl group, N-heptyl-2-pyrrolidinyl group, N-octyl-2-pyrrolidinyl group, N-methyl-3-pyrrolidinyl group, N-ethyl-3-pyrrolidinyl group, N-propyl-3-pyrrolidinyl group, N-butyl-3-pyrrolidinyl group, N-pentyl-3-pyrrolidinyl group, N-hexyl-3 -Pyrrolidinyl group, N-heptyl-3-pyrrolidinyl group, N-octyl-3-pyrrolidinyl group, N-methyl-2-piperidyl group, N-ethyl-2-pipe Zyl group, N-propyl-2-piperidyl group, N-butyl-2-piperidyl group, N-pentyl-2-piperidyl group, N-hexyl-2-piperidyl group, N-heptyl-2-piperidyl group, N- Octyl-2-piperidyl group, N-methyl-3-piperidyl group, N-ethyl-3-piperidyl group, N-propyl-3-piperidyl group, N-butyl-3-piperidyl group, N-pentyl-3-piperidyl group Group, N-hexyl-3-piperidyl group, N-heptyl-3-piperidyl group, N-octyl-3-piperidyl group, N-methyl-4-piperidyl group, N-ethyl-4-piperidyl group, N-propyl -4-piperidyl group, N-butyl-4-piperidyl group, N-pentyl-4-piperidyl group, N-hexyl-4-piperidyl group, N-heptyl-4-piperidyl group N-octyl-4-piperidyl group, N-methyl-2-pyrrolyl group, N-ethyl-2-pyrrolyl group, N-propyl-2-pyrrolyl group, N-butyl-2-pyrrolyl group, N-pentyl-2 -Pyrrolyl group, N-hexyl-2-pyrrolyl group, N-heptyl-2-pyrrolyl group, N-octyl-2-pyrrolyl group, N-methyl-3-pyrrolyl group, N-ethyl-3-pyrrolyl group, N -Propyl-3-pyrrolyl group, N-butyl-3-pyrrolyl group, N-pentyl-3-pyrrolyl group, N-hexyl-3-pyrrolyl group, N-heptyl-3-pyrrolyl group, N-octyl-3- Pyrrolyl group, N-methyl-2,3-dihydro-1H-2-pyrrolyl group, N-ethyl-2,3-dihydro-1H-2-pyrrolyl group, N-methyl-2,3-dihydro-1H-3 -Pyrrolyl group, N-ethyl -2,3-dihydro-1H-3-pyrrolyl group, N-methyl-2,3-dihydro-1H-4-pyrrolyl group, N-ethyl-2,3-dihydro-1H-4-pyrrolyl group, N- Methyl-2,3-dihydro-1H-5-pyrrolyl group, N-ethyl-2,3-dihydro-1H-5-pyrrolyl group, N-methyl-2,5-dihydro-1H-2-pyrrolyl group, N -Ethyl-2,5-dihydro-1H-2-pyrrolyl group, N-methyl-2,5-dihydro-1H-3-pyrrolyl group, N-ethyl-2,5-dihydro-1H-3-pyrrolyl group, N-methyl-1,2,3,4-tetrahydro-2-pyridyl group, N-methyl-1,2,3,4-tetrahydro-3-pyridyl group, N-methyl-1,2,3,4- Tetrahydro-4-pyridyl group, N-methyl-1,2,3,4-tetra Dro-5-pyridyl group, N-methyl-1,2,3,4-tetrahydro-6-pyridyl group, N-methyl-1,2,5,6-tetrahydro-2-pyridyl group, N-methyl-1 , 2,5,6-tetrahydro-3-pyridyl group, N-methyl-1,2,5,6-tetrahydro-4-pyridyl group, N-methyl-1,2,5,6-tetrahydro-5-pyridyl group Group, N-methyl-1,2,5,6-tetrahydro-6-pyridyl group, N-methyl-1,2-dihydro-2-pyridyl group, N-methyl-1,2-dihydro-3-pyridyl group N-methyl-1,2-dihydro-4-pyridyl group, N-methyl-1,2-dihydro-5-pyridyl group, N-methyl-1,2-dihydro-6-pyridyl group, N-methyl- 1H, 3H-2-pyridyl group, N-methyl-1H, 3H- -Pyridyl group, N-methyl-1H, 3H-4-pyridyl group, and the like, but are not necessarily limited to the groups exemplified here, and the heterocyclic non-aromatic third represented by the general formula (10) A group derived from a secondary amine may be used. The alkyl groups such as propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group and the like exemplified here are not limited to linear n-forms, but are isoforms, sec-forms, tert-forms. It may be branched or cyclic like a body.

  Specific examples of the acyclic quaternary ammonio group represented by the general formula (11) include, for example, a fluorinated trimethylammonio group, a trimethylammonio chloride group, a trimethylammonio bromide group, a trimethylammonio iodide group, Fluorinated triethylammonio group, triethylammoniochloride group, triethylammoniobromide group, triethylammonioiodide group, tripropylammoniofluoride group, tripropylammoniochloride group, tripropylammoniobromide group, Tripropylammonio iodide, tributylammoniofluoride, tributylammoniochloride, tributylammoniobromide, tributylammonioiodide, tripentylammoniochloride, tripentylammoniobromide, Tripentylammonio iodide, trihexylammonio chloride, Trihexyl ammonio group, trihexyl ammonio iodide, triheptyl ammonio chloride, triheptyl ammonio bromide, triheptyl ammonio iodide, trioctyl ammonio chloride, trioctyl ammonio bromide Group, trioctylammonio iodide, ethyldimethylammoniochloride, ethyldimethylammoniobromide, ethyldimethylammonioiodide, propyldimethylammoniochloride, propyldimethylammoniobromide, iodine Propyldimethylammonio group, butyldimethylammonio chloride, butyldimethylammoniobromide, butyldimethylammonioiodide, butyldimethylammoniochloride, butyldimethylammoniobromide, butyldimethylammonioiodide O group, propyldiethyl chloride Monio group, propyldiethylammonio group, propyldiethylammonio group, butyldiethylammoniochloride, butyldiethylammoniobromide group, butyldiethylammonioiodide group, triphenylammoniofluoride group, Triphenylammonio chloride, triphenylammoniobromide, triphenylammonioiodide, trinaphthylammoniofluoride, trinaphthylammoniochloride, trinaphthylammoniobromide, trinaphthyliodide Ammonio group, Dimethylphenylammonio group, Dimethylphenylammonio bromide, Dimethylphenylammonio iodide, Diethylphenylammonio chloride, Diethylphenylammonio bromide, Diethylphenylammonio iodide, Phenyldipropylammonio chloride Group, phenyldipropylammonio bromide group, phenyldipropylammonioiodide group, dibutylphenylammonio chloride, dibutylphenylammoniobromide, dibutylphenylammonioiodide, dimethylnaphthylammoniochloride, Dimethylnaphthylammonio bromide, dimethylnaphthylammonioiodide, diethylnaphthylammoniochloride, diethylnaphthylammoniobromide, diethylnaphthylammoniobromide, methyldiphenylammoniochloride, methyldiphenylammoniochloride, methyldiphenylbromide Ammonio group, methyldiphenylammonio iodide, ethyldiphenylammoniochloride, ethyldiphenylammoniobromide, ethyldiphenylammonioiodide, methyldinaphthylammoniochloride, methyldinaphthylammoniobromide Group, Methyl dinaphthyl ammonio group, ethyl dinaphthyl ammonio chloride, ethyl dinaphthyl ammonio bromide, ethyl dinaphthyl ammonio iodide, tribenzyl ammonio fluoride, tribenzyl ammonio chloride, Tribenzylammonio bromide, tribenzylammonio iodide, triphenethylammonio fluoride, triphenethylammonio chloride, triphenethylammonio bromide, triphenethylammonio iodide, benzyldimethyl chloride Ammonio group, benzyldimethylammonio bromide group, benzyldimethylammonio iodide group, benzyldiethylammonio chloride group, benzyldiethylammonio bromide group, benzyldiethylammonio iodide group, benzyldipropylammonio chloride group , Benzyldipropylan bromide Nio group, benzyldipropylammonio iodide, benzyldibutylammoniochloride, benzyldibutylammoniobromide, benzyldibutylammonioiodide, phenethyldimethylammoniochloride, phenethyldimethylammoniobromide, Phenethyldimethylammonio iodide, diethylphenethylammoniochloride, diethylphenethylammoniobromide, diethylphenethylammonioiodide, dibenzylmethylammoniochloride, dibenzylmethylammoniobromide, iodide Dibenzylmethylammonio group, dibenzylethylammonio chloride, dibenzylethylammoniobromide, dibenzylethylammonioiodide, diphenethylmethylammoniochloride, diphenethylmethylammoniobromide, Diphenetic iodide Rumethylammonio group, ethyl chloride diphenethyl ammonio group, ethyl diphenethyl ammonio bromide group, ethyl diphenethyl ammonio iodide group and the like, but not necessarily limited to the groups exemplified here, Any non-cyclic quaternary ammonio group represented by formula (11) can be used. The alkyl groups such as propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group and the like exemplified here are not limited to linear n-forms, but are isoforms, sec-forms, tert-forms. It may be branched or cyclic like a body.

  Specific examples of the heterocyclic non-aromatic quaternary ammonio group represented by the general formula (12) include, for example, a fluorinated N-methyl-1-pyrrolidinio group, a N-methyl-1-pyrrolidinio chloride group, and a bromide N -Methyl-1-pyrrolidinio group, iodide N-methyl-1-pyrrolidinio group, fluorinated N-ethyl-1-pyrrolidinio group, N-ethyl-1-pyrrolidinio chloride group, N-ethyl-1-pyrrolidinio bromide group N-ethyl-1-pyrrolidinio group, fluorinated N-propyl-1-pyrrolidinio group, N-propyl-1-pyrrolidinio chloride group, N-propyl-1-pyrrolidinio bromide group, N-propyl iodide 1-pyrrolidinio group, fluorinated N-butyl-1-pyrrolidinio group, N-butyl-1-pyrrolidinio chloride group, N-butyl-1-pyrrolidinio bromide group, N-butyl-1-iodide Loridinio group, N-pentyl-1-pyrrolidinio chloride group, N-pentyl-1-pyrrolidinio bromide group, N-pentyl-1-pyrrolidinio iodide group, N-hexyl-1-pyrrolidinio chloride group, N-hexyl bromide -1-pyrrolidinio group, iodide N-hexyl-1-pyrrolidinio group, chloride N-heptyl-1-pyrrolidinio group, bromide N-heptyl-1-pyrrolidinio group, iodide N-heptyl-1-pyrrolidinio group, chloride N-octyl-1-pyrrolidinio group, N-octyl-1-pyrrolidinio bromide group, Iodinated N-octyl-1-pyrrolidinio group, Fluorinated N-methyl-1-piperidinio group, N-methyl-1-piperidinio chloride Group, N-methyl-1-piperidinio bromide group, N-methyl-1-piperidinio iodide group, fluorinated N-ethyl-1-piperidinio group, N-ethyl-1-piperidinio group, brominated N-ethyl-1-piperidinio group, iodinated N-ethyl-1-piperidinio group, fluorinated N-propyl-1-piperidinio group, N-propyl-1-chloride Piperidinio group, N-propyl-1-piperidinio bromide group, N-propyl-1-piperidinio iodide, N-butyl-1-piperidinio fluoride group, N-butyl-1-piperidinio chloride group, N-bromide group Butyl-1-piperidinio group, iodinated N-butyl-1-piperidinio group, N-pentyl-1-piperidinio chloride group, N-pentyl-1-piperidinio bromide group, iodinated N-pentyl-1-piperidinio group, N-hexyl chloride-1-piperidinio group, N-hexyl bromide-1-piperidinio group, N-hexyl-1-piperidinio iodide group, N-heptyl chloride-1- Piperidinio group, N-heptyl-1-piperidinio bromide group, N-heptyl-1-piperidinio group iodide, N-octyl-1-piperidinio chloride group, N-octyl-1-piperidinio bromide group, N-iodide group Octyl-1-piperidinio group, fluorinated N-methyl-1-pyrrolinio group, N-methyl-1-pyrrolinio chloride group, N-methyl-1-pyrrolinio bromide group, N-methyl-1-pyrrolinio iodide group, Fluorinated N-ethyl-1-pyrrolinio group, N-ethyl-1-pyrrolinio chloride group, N-ethyl-1-pyrrolinio bromide group, N-ethyl-1-pyrrolinio iodide group, N-propyl-1 fluoride -Pyrrolinio group, N-propyl-1-pyrrolinio chloride group, N-propyl-1-pyrrolinio bromide group, N-propyl-1-pyrrolinio iodide group, N-butyl-1-pyrrole fluoride O group, N-butyl-1-pyrrolinio chloride group, N-butyl-1-pyrrolinio bromide group, N-butyl-1-pyrrolinio iodide group, N-pentyl-1-pyrrolinio chloride group, N-pentyl bromide group -1-pyrrolinio group, iodide N-pentyl-1-pyrrolinio group, N-hexyl chloride-1-pyrrolinio group, N-hexyl-1-pyrrolinio bromide group, iodide N-hexyl-1-pyrrolinio group, chloride N-heptyl-1-pyrrolinio group, N-heptyl-1-pyrrolinio bromide group, N-heptyl-1-pyrrolinio iodide group, N-octyl-1-pyrrolinio chloride group, N-octyl-1-pyrrolinio bromide group Group, iodinated N-octyl-1-pyrrolinio group, N-methyl-2,3-dihydro-1H-1-pyrrolinio chloride group, N-methyl-2,3-dihydro-1H-1-pyrrolinio group bromide Iodinated N-methyl-2,3-dihydro-1H-1-pyrrolinio group, N-ethyl-2,3-dihydro-1H-1-pyrrolinio chloride group, N-ethyl-2,3-dihydro-1H bromide -1-pyrrolinio group, iodinated N-ethyl-2,3-dihydro-1H-1-pyrrolinio group, N-methyl-2,5-dihydro-1H-1-pyrrolinio chloride group, N-methyl-2 bromide , 5-dihydro-1H-1-pyrrolinio group, iodide N-methyl-2,5-dihydro-1H-1-pyrrolinio group, N-ethyl-2,5-dihydro-1H-1-pyrrolinio group, odor N-ethyl-2,5-dihydro-1H-1-pyrrolinio group, iodinated N-ethyl-2,5-dihydro-1H-1-pyrrolinio group, N-methyl-1,2,3,4-iodine group Tetrahydro-1-pyridinio group, N-methyl bromide -1,2,3,4-tetrahydro-1-pyridinio group, N-methyl-1,2,3,4-tetrahydro-1-pyridinio iodide, N-ethyl-1,2,3,4- Tetrahydro-1-pyridinio group, N-ethyl-1,2,3,4-tetrahydro-1-pyridinio bromide group, N-ethyl-1,2,3,4-tetrahydro-1-pyridinio group iodide, chloride N-methyl-1,2,5,6-tetrahydro-1-pyridinio group, N-methyl-1,2,5,6-tetrahydro-1-pyridinio group bromide, iodide N-methyl-1,2, 5,6-tetrahydro-1-pyridinio group, N-ethyl-1,2,5,6-tetrahydro-1-pyridinio group, N-ethyl-1,2,5,6-tetrahydro-1-pyridinio bromide Group, N-ethyl iodide-1,2,5,6- Torahydro-1-pyridinio group, N-methyl-1,2-dihydro-1-pyridinio chloride, N-methyl-1,2-dihydro-1-pyridinio bromide, N-methyl-1,2-iodide Dihydro-1-pyridinio group, N-ethyl-1,2-dihydro-1-pyridinio chloride, N-ethyl-1,2-dihydro-1-pyridinio bromide, N-ethyl-1,2-iodide Dihydro-1-pyridinio group, chloride N-methyl-1H, 3H-1-pyridinio group, bromide N-methyl-1H, 3H-1-pyridinio group, iodide N-methyl-1H, 3H-1-pyridinio group N-ethyl-1H, 3H-1-pyridinio chloride, N-ethyl-1H, 3H-1-pyridinio bromide, N-ethyl-1H, 3H-1-pyridinio iodide, and the like. Not necessarily illustrated here Is not limited to groups, if heterocyclic aromatic quaternary ammonio group represented by the general formula (12) no problem. The alkyl groups such as propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group and the like exemplified here are not limited to linear n-forms, but are isoforms, sec-forms, tert-forms. It may be branched or cyclic like a body.

  Specific examples of the heterocyclic aromatic quaternary ammonio group represented by the general formula (13) include, for example, a fluorinated 1-pyridinio group, a 1-pyridinio chloride group, a 1-pyridinio bromide group, and a 1-pyridinio iodide. Group, 1-quinolinio fluoride group, 1-quinolinio chloride group, 1-quinolinio bromide group, 1-quinolinio iodide group, 2-isoquinolinio fluoride group, 2-isoquinolinio chloride group, 2-isoquinolinio bromide group, iodine group 2-isoquinolinio group etc. are mentioned.

Specific examples of the group derived from the heterocyclic non-aromatic quaternary ammonium ion represented by the general formula (14) include, for example, a fluorinated N, N-dimethylpyrrolidinium-2-yl group, N, N-chloride. Dimethylpyrrolidinium-2-yl group, N, N-dimethylpyrrolidinium-2-yl bromide group, N, N-dimethylpyrrolidinium-2-yl iodide group, N, N-diethylpyrrole fluoride Dinium-2-yl group, N, N-diethylpyrrolidinium-2-yl chloride group, N, N-diethylpyrrolidinium-2-yl bromide group, N, N-diethylpyrrolidinium iodide- 2-yl group, N, N-dipropylpyrrolidinium-2-yl fluoride, N, N-dipropylpyrrolidinium-2-yl chloride, N, N-dipropylpyrrolidinium bromide- 2-yl group, iodide N, N-dipropylpi Lidinium-2-yl group, fluorinated N, N-dibutylpyrrolidinium-2-yl group, N, N-dibutylpyrrolidinium-2-yl chloride group, N, N-dibutylpyrrolidinium-2 bromide -Yl group, iodide N, N-dibutylpyrrolidinium-2-yl group, N, N-dipentylpyrrolidinium-2-yl chloride group, N, N-dipentylpyrrolidinium-2-yl bromide group N, N-dipentylpyrrolidinium-2-yl iodide, N, N-dihexylpyrrolidinium-2-yl chloride, N, N-dihexylpyrrolidinium-2-yl bromide, iodide N, N-dihexylpyrrolidinium-2-yl group, N, N-diheptylpyrrolidinium-2-yl chloride, N, N-diheptylpyrrolidinium-2-yl bromide, N-iodide , N-diheptylpyrrolidinium- -Yl group, N, N-dioctylpyrrolidinium-2-yl chloride group, N, N-dioctylpyrrolidinium-2-yl bromide group, N, N-dioctylpyrrolidinium-2-yl iodide group N, N-ethylmethylpyrrolidinium-2-yl chloride group, N, N-ethylmethylpyrrolidinium-2-yl bromide group, N, N-ethylmethylpyrrolidinium-2-yl iodide group N, N-methylpropylpyrrolidinium-2-yl chloride group, N, N-methylpropylpyrrolidinium-2-yl bromide group, N, N-methylpropylpyrrolidinium-2-yl iodide group N, N-butylmethylpyrrolidinium-2-yl chloride, N, N-butylmethylpyrrolidinium-2-yl bromide, N, N-butylmethylpyrrolidinium-2-yl iodide N, N-ethylpropyl chloride Rupyrrolidinium-2-yl group, N, N-ethylpropylpyrrolidinium-2-yl bromide group, N, N-ethylpropylpyrrolidinium-2-yl iodide group, N, N-butylethylpyrrolidichloride Ni-2-yl group, N, N-butylethylpyrrolidinium-2-yl bromide group, N, N-butylethylpyrrolidinium-2-yl iodide group, N, N-butylpropylpyrrolidichloride Ni-2-yl group, N, N-butylpropylpyrrolidinium-2-yl bromide group, N, N-butylpropylpyrrolidinium-2-yl iodide group, N, N-dimethylpyrrolidifluoride group Ni-3-yl group, N, N-dimethylpyrrolidinium-3-yl chloride, N, N-dimethylpyrrolidinium-3-yl bromide, N, N-dimethylpyrrolidinium iodide-3 -Yl group, fluoride N N-diethylpyrrolidinium-3-yl group, N, N-diethylpyrrolidinium-3-yl chloride, N, N-diethylpyrrolidinium-3-yl bromide, N, N-diethyl iodide Pyrrolidinium-3-yl group, fluorinated N, N-dipropylpyrrolidinium-3-yl group, N, N-dipropylpyrrolidinium-3-yl chloride chloride, N, N-dipropyl bromide Pyrrolidinium-3-yl group, N, N-dipropylpyrrolidinium-3-yl iodide, N, N-dibutylpyrrolidinium-3-yl fluoride, N, N-dibutylpyrrolidichloride Ni-3-yl group, N, N-dibutylpyrrolidinium-3-yl bromide, N, N-dibutylpyrrolidinium-3-yl iodide, N, N-dipentylpyrrolidinium-3 chloride -Yl group, N, N-dipentylpyrrole bromide Ni-3-yl group, N, N-dipentylpyrrolidinium-3-yl iodide, N, N-dihexylpyrrolidinium-3-yl chloride, N, N-dihexylpyrrolidinium-3 bromide -Yl group, N, N-dihexylpyrrolidinium-3-yl iodide, N, N-diheptylpyrrolidinium-3-yl chloride, N, N-diheptylpyrrolidinium bromide-3- Yl group, iodide N, N-diheptylpyrrolidinium-3-yl group, N, N-dioctylpyrrolidinium-3-yl chloride, N, N-dioctylpyrrolidinium-3-yl bromide group N, N-dioctylpyrrolidinium-3-yl iodide, N, N-ethylmethylpyrrolidinium-3-yl chloride, N, N-ethylmethylpyrrolidinium-3-yl bromide, N, N-ethylmethylpyrrolidiiodide Ni-3-yl group, N, N-methylpropylpyrrolidinium-3-yl chloride, N, N-methylpropylpyrrolidinium-3-yl bromide, N, N-methylpropylpyrrolidi iodide Ni-3-yl group, N, N-butylmethylpyrrolidinium-3-yl chloride, N, N-butylmethylpyrrolidinium-3-yl bromide, N, N-butylmethylpyrrolidi iodide Ni-3-yl group, N, N-ethylpropylpyrrolidinium-3-yl chloride, N, N-ethylpropylpyrrolidinium-3-yl bromide, N, N-ethylpropylpyrrolidi iodide Ni-3-yl group, N, N-butylethylpyrrolidinium-3-yl chloride, N, N-butylethylpyrrolidinium-3-yl bromide, N, N-butylethylpyrrolidi iodide Ni-3-yl group, salt N, N-butylpropylpyrrolidinium-3-yl group, N, N-butylpropylpyrrolidinium-3-yl bromide group, N, N-butylpropylpyrrolidinium-3-yl iodide group, N, N-dimethylpiperidinium-2-yl group, N, N-dimethylpiperidinium-2-yl chloride group, N, N-dimethylpiperidinium-2-yl bromide group, N-iodide group, N-dimethylpiperidinium-2-yl group, fluorinated N, N-diethylpiperidinium-2-yl group, N, N-diethylpiperidinium-2-yl chloride group, N, N-diethyl bromide Piperidinium-2-yl group, iodide N, N-diethylpiperidinium-2-yl group, fluoride N, N-dipropylpiperidinium-2-yl group, N, N-dipropylpi Peridinium-2-yl group, N, N bromide Dipropylpiperidinium-2-yl group, iodide N, N-dipropylpiperidinium-2-yl group, fluorinated N, N-dibutylpiperidinium-2-yl group, N, N-dibutyl chloride Piperidinium-2-yl group, N, N-dibutylpiperidinium-2-yl bromide group, N, N-dibutylpiperidinium-2-yl iodide, N, N-dipentylpiperidinium chloride 2-yl group, N, N-dipentylpiperidinium-2-yl bromide group, iodide N, N-dipentylpiperidinium-2-yl group, N, N-dihexylpiperidinium-2-chloride Yl group, N, N-dihexylpiperidinium-2-yl bromide group, iodide N, N-dihexylpiperidinium-2-yl group, N, N-diheptylpiperidinium-2-yl chloride group N, N-diheptyl pipette bromide Lidinium-2-yl group, N, N-diheptylpiperidinium-2-yl iodide, N, N-dioctylpiperidinium-2-yl chloride group, N, N-dioctylpiperidinium bromide- 2-yl group, N, N-dioctylpiperidinium-2-yl iodide, N, N-ethylmethylpiperidinium-2-yl chloride, N, N-ethylmethylpiperidinium-2 bromide -Yl group, N, N-ethylmethylpiperidinium-2-yl iodide, N, N-methylpropylpiperidinium-2-yl chloride, N, N-methylpropylpiperidinium-2 bromide -Yl group, N, N-methylpropylpiperidinium-2-yl iodide, N, N-butylmethylpiperidinium-2-yl chloride, N, N-butylmethylpiperidinium-2 bromide-2 -Yl group, iodide N, N Butylmethylpiperidinium-2-yl group, N, N-ethylpropylpiperidinium-2-yl chloride, N, N-ethylpropylpiperidinium-2-yl bromide, N, N-iodide Ethylpropylpiperidinium-2-yl group, N, N-butylethylpiperidinium-2-yl chloride, N, N-butylethylpiperidinium-2-yl bromide, N, N-iodide Butylethylpiperidinium-2-yl group, N, N-butylpropylpiperidinium-2-yl chloride, N, N-butylpropylpiperidinium-2-yl bromide, N, N-iodide Butylpropylpiperidinium-2-yl group, fluorinated N, N-dimethylpiperidinium-3-yl group, N, N-dimethylpiperidinium-3-yl chloride group, N, N-dimethylpimide bromide Peridinium-3- Group, iodinated N, N-dimethylpiperidinium-3-yl group, fluorinated N, N-diethylpiperidinium-3-yl group, N, N-diethylpiperidinium-3-yl chloride group, N, N-diethylpiperidinium-3-yl bromide, N, N-diethylpiperidinium-3-yl iodide, N, N-dipropylpiperidinium-3-yl fluoride, chloride N, N-dipropylpiperidinium-3-yl group, brominated N, N-dipropylpiperidinium-3-yl group, iodide N, N-dipropylpiperidinium-3-yl group, fluorine N, N-dibutylpiperidinium-3-yl group, N, N-dibutylpiperidinium-3-yl chloride, N, N-dibutylpiperidinium-3-yl bromide, N-iodide, N-dibutylpiperidinium-3-yl group, N, N-dichloride Pentylpiperidinium-3-yl group, N, N-dipentylpiperidinium-3-yl bromide group, N, N-dipentylpiperidinium-3-yl iodide group, N, N-dihexylpiperidi chloride Nitro-3-yl group, N, N-dihexylpiperidinium-3-yl bromide group,
N, N-dihexylpiperidinium-3-yl iodide, N, N-diheptylpiperidinium-3-yl chloride, N, N-diheptylpiperidinium-3-yl bromide, iodine N, N-diheptylpiperidinium-3-yl group, N, N-dioctylpiperidinium-3-yl chloride group, N, N-dioctylpiperidinium-3-yl bromide group, N-iodide group N-dioctylpiperidinium-3-yl group, N, N-ethylmethylpiperidinium-3-yl chloride, N, N-ethylmethylpiperidinium-3-yl bromide, N-iodide, N-ethylmethylpiperidinium-3-yl group, N, N-methylpropylpiperidinium-3-yl chloride, N, N-methylpropylpiperidinium-3-yl bromide, N-iodide, N-methylpropylpiperidinium- -Yl group, N, N-butylmethylpiperidinium-3-yl chloride, N, N-butylmethylpiperidinium-3-yl bromide, N, N-butylmethylpiperidinium-3 iodide -Yl group, N, N-ethylpropylpiperidinium-3-yl chloride, N, N-ethylpropylpiperidinium-3-yl bromide, N, N-ethylpropylpiperidinium-3 iodide -Yl group, N, N-butylethylpiperidinium-3-yl chloride, N, N-butylethylpiperidinium-3-yl bromide, N, N-butylethylpiperidinium-3 iodide -Yl group, N, N-butylpropylpiperidinium-3-yl group, N, N-butylpropylpiperidinium-3-yl bromide group, N, N-butylpropylpiperidinium-3 iodide -Yl group, fluoride N, -Dimethylpiperidinium-4-yl group, N, N-dimethylpiperidinium-4-yl chloride, N, N-dimethylpiperidinium-4-yl bromide, N, N-dimethylpiido iodide Peridinium-4-yl group, fluorinated N, N-diethylpiperidinium-4-yl group, N, N-diethylpiperidinium-4-yl chloride, N, N-diethylpiperidinium bromide- 4-yl group, iodide N, N-diethylpiperidinium-4-yl group, fluorinated N, N-dipropylpiperidinium-4-yl group, N, N-dipropylpiperidinium chloride-4 -Yl group, N, N-dipropylpiperidinium-4-yl bromide group, N, N-dipropylpiperidinium-4-yl iodide, N, N-dibutylpiperidinium fluoride-4 -Yl group, N, N-dibutylpiperidinium chloride Mu-4-yl group, N, N-dibutylpiperidinium-4-yl bromide group, N, N-dibutylpiperidinium-4-yl iodide, N, N-dipentylpiperidinium chloride-4 -Yl group, N, N-dipentylpiperidinium-4-yl bromide group, N, N-dipentylpiperidinium-4-yl iodide group, N, N-dihexylpiperidinium-4-yl chloride group N, N-dihexylpiperidinium-4-yl bromide, N, N-dihexylpiperidinium-4-yl iodide, N, N-diheptylpiperidinium-4-yl chloride, odor N, N-diheptylpiperidinium-4-yl group, iodide N, N-diheptylpiperidinium-4-yl group, N, N-dioctylpiperidinium-4-yl chloride, bromide N, N-Dioctylpiperidinium-4-yl N, N-dioctylpiperidinium-4-yl iodide, N, N-ethylmethylpiperidinium-4-yl chloride, N, N-ethylmethylpiperidinium-4-yl bromide, N, N-ethylmethylpiperidinium-4-yl group iodide, N, N-methylpropylpiperidinium-4-yl chloride group, N, N-methylpropylpiperidinium-4-yl bromide group, N, N-methylpropylpiperidinium-4-yl group iodide, N, N-butylmethylpiperidinium-4-yl chloride group, N, N-butylmethylpiperidinium-4-yl bromide group, N, N-butylmethylpiperidinium-4-yl group, N, N-ethylpropylpiperidinium-4-yl chloride group, N, N-ethylpropylpiperidinium-4-yl bromide group, N, N-ethyl iodide Pyrpiperidinium-4-yl group, N, N-butylethylpiperidinium-4-yl group chloride, N, N-butylethylpiperidinium-4-yl bromide group, N, N-butyl iodide Ethylpiperidinium-4-yl group, N, N-butylpropylpiperidinium-4-yl chloride, N, N-butylpropylpiperidinium-4-yl bromide, N, N-butyl iodide Propylpiperidinium-4-yl group, Fluorinated N, N-dimethylpyrrolin-2-yl group, N, N-dimethylpyrrolinium-2-yl chloride, N, N-dimethylpyrrolinium-2 bromide -Yl group, N, N-dimethylpyrrolinium-2-yl iodide, N, N-diethylpyrrolinium-2-yl fluoride, N, N-diethylpyrrolin-2-yl chloride, bromide N, N-diethylpyrrolinium Mu-2-yl group, N, N-diethylpyrrolinium-2-yl iodide, N, N-dipropylpyrrolin-2-yl fluoride, N, N-dipropylpyrrolinium-2-chloride Yl, N, N-dipropylpyrrolin-2-yl bromide, N, N-dipropylpyrrolin-2-yl iodide, N, N-dibutylpyrrolin-2-yl fluoride, N, N-dibutylpyrrolin-2-yl chloride group, N, N-dibutylpyrrolin-2-yl bromide group,
N, N-dibutylpyrrolin-2-yl iodide, N, N-dipentylpyrrolin-2-yl chloride, N, N-dipentylpyrrolin-2-yl bromide, N, N-iodide Dipentylpyrrolinium-2-yl group, N, N-dihexylpyrrolin-2-yl chloride group, N, N-dihexylpyrrolin-2-yl bromide group, N, N-dihexylpyrrolinium-2-iodide group Yl group, N, N-diheptylpyrrolin-2-yl chloride, N, N-diheptylpyrrolin-2-yl bromide, N, N-diheptylpyrrolin-2-yl iodide, N, N-dioctylpyrrolin-2-yl chloride, N, N-dioctylpyrrolin-2-yl bromide, N, N-dioctylpyrrolin-2-yl iodide, N, N-ethyl chloride Methylpyrrolinium 2-yl group, N, N-ethylmethylpyrrolinium-2-yl bromide group, N, N-ethylmethylpyrrolinium-2-yl iodide group, N, N-methylpropylpyrrolinium-2-chloride group Yl, N, N-methylpropylpyrrolin-2-yl bromide, N, N-methylpropylpyrrolin-2-yl iodide, N, N-butylmethylpyrrolin-2-yl chloride, N, N-butylmethylpyrrolin-2-yl bromide, N, N-butylmethylpyrrolin-2-yl iodide, N, N-ethylpropylpyrrolin-2-yl chloride, N bromide , N-ethylpropylpyrrolin-2-yl group, iodide N, N-ethylpropylpyrrolin-2-yl group, N, N-butylethylpyrrolin-2-yl chloride, N, N-bromide Butylethyl pylori Um-2-yl group, N, N-butylethylpyrrolin-2-yl iodide group, N, N-butylpropylpyrrolin-2-yl chloride group, N, N-butylpropylpyrrolinium-2 bromide -Yl group, iodide N, N-butylpropylpyrrolin-2-yl group, fluoride N, N-dimethylpyrrolin-3-yl group, N, N-dimethylpyrrolin-3-yl chloride, odor N, N-dimethylpyrrolin-3-yl group, N, N-dimethylpyrrolin-3-yl iodide, N, N-diethylpyrrolin-3-yl group, N, N-diethyl chloride Pyrrolium-3-yl group, N, N-diethylpyrrolium-3-yl bromide group, N, N-diethylpyrrolium-3-yl iodide, N, N-dipropylpyrrolium-3 fluoride -Yl group, N, N- chloride Dipropylpyrrolin-3-yl group, N, N-dipropylpyrrolinium-3-yl bromide group, N, N-dipropylpyrrolinium-3-yl iodide, N, N-dibutylpyrrole fluoride Ni-3-yl group, N, N-dibutylpyrrolin-3-yl chloride, N, N-dibutylpyrrolin-3-yl bromide, N, N-dibutylpyrrolin-3-yl iodide group N, N-dipentylpyrrolin-3-yl chloride, N, N-dipentylpyrrolin-3-yl bromide, N, N-dipentylpyrrolin-3-yl iodide, N, N-chloride Dihexylpyrrolin-3-yl group, N, N-dihexylpyrrolin-3-yl bromide, N, N-dihexylpyrrolin-3-yl iodide, N, N-diheptylpyrrolinium-3 chloride -Yl group, bromide N, N-diheptylpyrrolin-3-yl group, iodide N, N-diheptylpyrrolin-3-yl group, N, N-dioctylpyrrolin-3-yl chloride, N, N-dioctyl bromide Pyrrolin-3-yl group, iodide N, N-dioctylpyrrolin-3-yl group, N, N-ethylmethylpyrrolin-3-yl chloride, N, N-ethylmethylpyrrolinium-3 bromide -Yl group, iodide N, N-ethylmethylpyrrolin-3-yl group, N, N-methylpropylpyrrolin-3-yl chloride, N, N-methylpropylpyrrolin-3-yl bromide group N, N-methylpropylpyrrolin-3-yl group iodide, N, N-butylmethylpyrrolin-3-yl chloride group, N, N-butylmethylpyrrolin-3-yl bromide group, iodide N, N-B Rumethylpyrrolin-3-yl group, N, N-ethylpropylpyrrolin-3-yl chloride, N, N-ethylpropylpyrrolin-3-yl bromide, N, N-ethylpropylpyrrole iodide Ni-3-yl group, N, N-butylethylpyrrolin-3-yl chloride, N, N-butylethylpyrrolin-3-yl bromide, N, N-butylethylpyrrolinium iodide-3 -Yl group, N, N-butylpropylpyrrolin-3-yl chloride, N, N-butylpropylpyrrolin-3-yl bromide, N, N-butylpropylpyrrolin-3-yl iodide N, N-dimethyl-2,3-dihydro-1H-pyrrolin-2-yl chloride, N, N-dimethyl-2,3-dihydro-1H-pyrrolin-2-yl bromide, N-iodide, N-dimethyl Lu-2,3-dihydro-1H-pyrrolin-2-yl group, N, N-diethyl-2,3-dihydro-1H-pyrrolin-2-yl chloride, N, N-diethyl-2,3 bromide -Dihydro-1H-pyrrolin-2-yl group, iodide N, N-diethyl-2,3-dihydro-1H-pyrrolin-2-yl group, N, N-dimethyl-2,3-dihydro-1H- chloride Pyrrolium-3-yl group, N, N-dimethyl-2,3-dihydro-1H-pyrrolinium-3-yl bromide group, N, N-dimethyl-2,3-dihydro-1H-pyrrolium-3-iodide group Yl group, N, N-diethyl-2,3-dihydro-1H-pyrrolin-3-yl group, N, N-diethyl-2,3-dihydro-1H-pyrrolin-3-yl group, iodide N, N-diethyl-2,3- Hydro-1H-pyrrolin-3-yl group, N, N-dimethyl-2,3-dihydro-1H-pyrrolin-4-yl group, N, N-dimethyl-2,3-dihydro-1H-pyrrolinium bromide -4-yl group, iodide N, N-dimethyl-2,3-dihydro-1H-pyrrolin-4-yl group, N, N-diethyl-2,3-dihydro-1H-pyrrolin-4-yl group N, N-diethyl-2,3-dihydro-1H-pyrrolin-4-yl group bromide, N, N-diethyl-2,3-dihydro-1H-pyrrolin-4-yl group iodide, N, chloride N-dimethyl-2,3-dihydro-1H-pyrrolin-5-yl group, N, N-dimethyl-2,3-dihydro-1H-pyrrolinium-5-yl bromide group, iodide N, N-dimethyl- 2,3-dihydro-1 -Pyrrolonium-5-yl group, N, N-diethyl-2,3-dihydro-1H-pyrrolium-5-yl group, N, N-diethyl-2,3-dihydro-1H-pyrrolinium-5-bromide Yl group, iodide N, N-diethyl-2,3-dihydro-1H-pyrrolin-5-yl group, N, N-dimethyl-2,5-dihydro-1H-pyrrolin-2-yl chloride, bromide N, N-dimethyl-2,5-dihydro-1H-pyrrolin-2-yl group, iodide N, N-dimethyl-2,5-dihydro-1H-pyrrolin-2-yl group, N, N-diethyl chloride -2,5-dihydro-1H-pyrrolin-2-yl group, N, N-diethyl-2,5-dihydro-1H-pyrrolin-2-yl group, N, N-diethyl-2,5 iodide -Dihydro-1H-pyrrolinium Mu-2-yl group, N, N-dimethyl-2,5-dihydro-1H-pyrrolin-3-yl group, N, N-dimethyl-2,5-dihydro-1H-pyrrolin-3-yl bromide Group,
N, N-dimethyl-2,5-dihydro-1H-pyrrolin-3-yl group, iodide N, N-diethyl-2,5-dihydro-1H-pyrrolin-3-yl group, N, N bromide -Diethyl-2,5-dihydro-1H-pyrrolin-3-yl group, iodide N, N-diethyl-2,5-dihydro-1H-pyrrolin-3-yl group, N, N-dimethyl-1, chloride 2,3,4-tetrahydropyridinium-2-yl group, N, N-dimethyl-1,2,3,4-tetrahydropyridinium-2-yl bromide group, N, N-dimethyl-1,2, iodide group 3,4-tetrahydropyridinium-2-yl group, N, N-dimethyl-1,2,3,4-tetrahydropyridinium-3-yl chloride, N, N-dimethyl-1,2,3,4 -Tetrahydropyridinium-3- N, N-dimethyl-1,2,3,4-tetrahydropyridinium-3-yl group, N, N-dimethyl-1,2,3,4-tetrahydropyridinium-4-yl chloride group, N, N-dimethyl-1,2,3,4-tetrahydropyridinium-4-yl group, bromide N, N-dimethyl-1,2,3,4-tetrahydropyridinium-4-yl group, N chloride , N-dimethyl-1,2,3,4-tetrahydropyridinium-5-yl group, N, N-dimethyl-1,2,3,4-tetrahydropyridinium-5-yl bromide group, iodide N, N -Dimethyl-1,2,3,4-tetrahydropyridinium-5-yl group, N, N-dimethyl-1,2,3,4-tetrahydropyridinium-6-yl chloride group, N, N-dimethylbromide 1,2,3,4-tetra Dropyridinium-6-yl group, iodide N, N-dimethyl-1,2,3,4-tetrahydropyridinium-6-yl group, N, N-dimethyl-1,2,5,6-tetrahydropyridinium chloride- 2-yl group, N, N-dimethyl-1,2,5,6-tetrahydropyridinium-2-yl bromide group, N, N-dimethyl-1,2,5,6-tetrahydropyridinium-2-iodide Yl group, N, N-dimethyl-1,2,5,6-tetrahydropyridinium-3-yl group, N, N-dimethyl-1,2,5,6-tetrahydropyridinium-3-yl bromide group, N, N-dimethyl-1,2,5,6-tetrahydropyridinium-3-yl iodide, N, N-dimethyl-1,2,5,6-tetrahydropyridinium-4-yl chloride, N-bromide , N-dimethyl- 1,2,5,6-tetrahydropyridinium-4-yl group, iodide N, N-dimethyl-1,2,5,6-tetrahydropyridinium-4-yl group, N, N-dimethyl-1,2 chloride , 5,6-Tetrahydropyridinium-5-yl group, N, N-dimethyl-1,2,5,6-tetrahydropyridinium-5-yl bromide group, N, N-dimethyl-1,2,5 iodide , 6-Tetrahydropyridinium-5-yl group, N, N-dimethyl-1,2,5,6-tetrahydropyridinium-6-yl chloride, N, N-dimethyl-1,2,5,6-bromide group Tetrahydropyridinium-6-yl group, iodide N, N-dimethyl-1,2,5,6-tetrahydropyridinium-6-yl group, N, N-dimethyl-1,2-dihydropyridinium-2-yl chloride group , N, N bromide Dimethyl-1,2-dihydropyridinium-2-yl group, iodide N, N-dimethyl-1,2-dihydropyridinium-2-yl group, N, N-dimethyl-1,2-dihydropyridinium-3-chloride Yl group, N, N-dimethyl-1,2-dihydropyridinium-3-yl bromide group, N, N-dimethyl-1,2-dihydropyridinium-3-yl iodide group, N, N-dimethyl chloride 1,2-dihydropyridinium-4-yl group, N, N-dimethyl-1,2-dihydropyridinium-4-yl bromide group, N, N-dimethyl-1,2-dihydropyridinium-4-yl iodide Group, N, N-dimethyl-1,2-dihydropyridinium-5-yl chloride, N, N-dimethyl-1,2-dihydropyridinium-5-yl bromide, N, N-dimethyl-1 iodide , 2 Dihydropyridinium-5-yl group, N, N-dimethyl-1,2-dihydropyridinium-6-yl chloride, N, N-dimethyl-1,2-dihydropyridinium-6-yl bromide, N-iodide , N-dimethyl-1,2-dihydropyridinium-6-yl group, N, N-dimethyl-1H, 3H-pyridinium-2-yl chloride group, N, N-dimethyl-1H, 3H-pyridinium-2 bromide -Yl group, iodinated N, N-dimethyl-1H, 3H-pyridinium-2-yl group, N, N-dimethyl-1H, 3H-pyridinium-3-yl chloride, N, N-dimethyl-1H bromide , 3H-pyridinium-3-yl group, N, N-dimethyl-1H, 3H-pyridinium-3-yl iodide, N, N-dimethyl-1H, 3H-pyridinium-4-yl group, bromide N , N-di Examples thereof include a methyl-1H, 3H-pyridinium-4-yl group and an iodide N, N-dimethyl-1H, 3H-pyridinium-4-yl group, but are not necessarily limited to the groups exemplified here. Any group derived from a heterocyclic non-aromatic quaternary ammonium ion represented by the formula (14) may be used. The alkyl groups such as propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group and the like exemplified here are not limited to linear n-forms, but are isoforms, sec-forms, tert-forms. It may be branched or cyclic like a body.

Specific examples of the group derived from the heterocyclic aromatic quaternary ammonium ion represented by the general formula (15) include, for example, a fluorinated N-methylpyridinium-2-yl group and an N-methylpyridinium-2-yl chloride group. N-methylpyridinium-2-yl bromide group, N-methylpyridinium-2-yl iodide group, N-ethylpyridinium-2-yl fluoride group, N-ethylpyridinium-2-yl chloride group, bromide N-ethylpyridinium-2-yl group, N-ethylpyridinium-2-yl iodide group, N-propylpyridinium-2-yl fluoride group, N-propylpyridinium-2-yl chloride group, N-propyl bromide Pyridinium-2-yl group, iodide N-propylpyridinium-2-yl group, fluorinated N-butylpyridinium-2-yl group, N-butylpyridinium chloride-2 Yl group, N-butylpyridinium-2-yl bromide group, N-butylpyridinium-2-yl iodide group, N-pentylpyridinium-2-yl fluoride group, N-pentylpyridinium-2-yl chloride group, N-pentylpyridinium-2-yl bromide group, N-pentylpyridinium-2-yl iodide group, N-hexylpyridinium-2-yl fluoride group, N-hexylpyridinium-2-yl chloride group, bromide N -Hexylpyridinium-2-yl group, N-hexylpyridinium-2-yl iodide, N-heptylpyridinium-2-yl fluoride, N-heptylpyridinium-2-yl chloride, N-heptylpyridinium bromide 2-yl group, iodinated N-heptylpyridinium-2-yl group, fluorinated N-octylpyridinium-2-yl group, N-octyl chloride Pyridinium-2-yl group, N-octylpyridinium-2-yl bromide group, N-octylpyridinium-2-yl iodide, N-methylpyridinium-3-yl fluoride group, N-methylpyridinium chloride-3 -Yl group, N-methylpyridinium-3-yl bromide group, N-methylpyridinium-3-yl iodide, N-ethylpyridinium-3-yl fluoride group, N-ethylpyridinium-3-yl chloride group N-ethylpyridinium-3-yl bromide, N-ethylpyridinium-3-yl iodide, N-propylpyridinium-3-yl fluoride, N-propylpyridinium-3-yl chloride, bromide N-propylpyridinium-3-yl group, iodide N-propylpyridinium-3-yl group, fluorinated N-butylpyridinium-3-yl group, N-butyl chloride Rupyridinium-3-yl group, N-butylpyridinium-3-yl bromide group, N-butylpyridinium-3-yl iodide, N-pentylpyridinium-3-yl fluoride group, N-pentylpyridinium chloride- 3-yl group, N-pentylpyridinium-3-yl bromide group, N-pentylpyridinium-3-yl iodide, N-hexylpyridinium-3-yl fluoride group, N-hexylpyridinium-3-yl chloride Group, N-hexylpyridinium-3-yl bromide group, N-hexylpyridinium-3-yl iodide, N-heptylpyridinium-3-yl fluoride group, N-heptylpyridinium-3-yl chloride group, odor N-heptylpyridinium-3-yl group, N-heptylpyridinium-3-yl iodide, N-octylpyridinium-3-yl fluoride N-octylpyridinium-3-yl chloride, N-octylpyridinium-3-yl bromide, N-octylpyridinium-3-yl iodide, N-methylpyridinium-4-yl fluoride, N chloride -Methylpyridinium-4-yl group, N-methylpyridinium-4-yl bromide group, N-methylpyridinium-4-yl iodide, N-ethylpyridinium-4-yl fluoride group, N-ethylpyridinium chloride -4-yl group, N-ethylpyridinium-4-yl bromide group, N-ethylpyridinium-4-yl iodide, N-propylpyridinium-4-yl fluoride group, N-propylpyridinium chloride-4- Yl group, N-propylpyridinium-4-yl bromide group, N-propylpyridinium-4-yl iodide group, N-butylpyridinium fluoride-4- Group, N-butylpyridinium-4-yl chloride group, N-butylpyridinium-4-yl bromide group, N-butylpyridinium-4-yl iodide group, N-pentylpyridinium-4-yl fluoride group, N-pentylpyridinium-4-yl chloride, N-pentylpyridinium-4-yl bromide, N-pentylpyridinium-4-yl iodide, N-hexylpyridinium-4-yl fluoride, N-chloride Hexylpyridinium-4-yl group, N-hexylpyridinium-4-yl bromide group, N-hexylpyridinium-4-yl iodide, N-heptylpyridinium-4-yl fluoride group, N-heptylpyridinium chloride- 4-yl group, N-heptylpyridinium-4-yl bromide group, N-heptylpyridinium-4-yl iodide, N-octylpyrifluoride group Dinium-4-yl group, N-octylpyridinium-4-yl group chloride, N-octylpyridinium-4-yl bromide group, N-octylpyridinium-4-yl iodide group, N-methylquinolinium chloride- 2-yl group, N-methylquinolinium-2-yl bromide group, N-methylquinolinium-2-yl iodide group, N-ethylquinolinium-2-yl chloride group, N-bromide group Ethylquinolinium-2-yl group, N-ethylquinolinium-2-yl iodide group, N-propylquinolinium-2-yl chloride group, N-propylquinolinium-2-yl bromide group N-propylquinolinium-2-yl iodide, N-butylquinolinium-2-yl chloride, N-butylquinolinium-2-yl bromide, N-butylquinolinium iodide 2-yl group, N-methylquinolini chloride Mu-3-yl group, N-methylquinolinium-3-yl bromide group, N-methylquinolinium-3-yl iodide, N-ethylquinolinium-3-yl chloride group, bromide N-ethylquinolinium-3-yl group, N-ethylquinolinium-3-yl iodide, N-propylquinolinium-3-yl chloride group, N-propylquinolinium bromide-3- Yl group, N-propylquinolinium-3-yl iodide, N-butylquinolinium-3-yl chloride, N-butylquinolinium-3-yl bromide, N-butyl iodide Norinium-3-yl group, N-methylquinolinium-4-yl chloride, N-methylquinolinium-4-yl bromide, N-methylquinolinium-4-yl iodide, chloride N-ethylquinolinium-4-yl group, N-ethylquinolinium-4-bromide Group, N-ethylquinolinium-4-yl iodide, N-propylquinolinium-4-yl chloride, N-propylquinolinium-4-yl bromide, N-propyl iodide Norinium-4-yl group, N-butylquinolinium-4-yl chloride, N-butylquinolinium-4-yl bromide, N-butylquinolinium-4-yl iodide, chloride N-methylquinolinium-5-yl group, N-methylquinolinium-5-yl group bromide, N-methylquinolinium-5-yl iodide, N-ethylquinolinium chloride-5- Yl group, N-ethylquinolinium-5-yl group bromide, N-ethylquinolinium-5-yl group iodide, N-propylquinolinium-5-yl chloride group, N-propyl group bromide Norinium-5-yl group, N-propylquinolinium-5-yl iodide Group, N-butylquinolinium-5-yl chloride, N-butylquinolinium-5-yl bromide, N-butylquinolinium-5-yl iodide, N-methylquinolinium chloride -6-yl, N-methylquinolinium-6-yl bromide, N-methylquinolinium-6-yl iodide, N-ethylquinolinium-6-yl chloride, N-bromide -Ethylquinolinium-6-yl group, N-ethylquinolinium-6-yl iodide, N-propylquinolinium-6-yl chloride, N-propylquinolinium-6-yl bromide Group, N-propylquinolinium-6-yl iodide, N-butylquinolinium-6-yl chloride, N-butylquinolinium-6-yl bromide, N-butylquinol iodide Nitro-6-yl group, N-methylquinolinium-7-yl chloride, N-bromide Methylquinolinium-7-yl group, N-methylquinolinium-7-yl iodide, N-ethylquinolinium-7-yl chloride, N-ethylquinolinium-7-yl bromide group N-ethylquinolinium-7-yl iodide, N-propylquinolinium-7-yl chloride, N-propylquinolinium-7-yl bromide, N-propylquinolinium iodide -7-yl group, N-butylquinolinium chloride-7-yl group, N-butylquinolinium bromide-7-yl bromide group, N-butyl quinolinium-7-yl iodide group, N-chloride chloride Methylquinolinium-8-yl group, N-methylquinolinium-8-yl bromide group, N-methylquinolinium-8-yl iodide group, N-ethylquinolinium-8-yl group chloride N-ethylquinolinium-8-yl bromide, N-ethyl iodide Noriniumu 8-yl group,
N-propylquinolinium-8-yl chloride group, N-propylquinolinium-8-yl bromide group, N-propylquinolinium-8-yl iodide group, N-butylquinolinium chloride-8 -Yl group, N-butylquinolinium-2-yl bromide group, N-butylquinolinium-8-yl iodide, N-methylisoquinolinium-1-yl chloride group, N-bromide Methylisoquinolinium-1-yl group, N-methylisoquinolinium-1-yl iodide, N-ethylisoquinolinium-1-yl chloride, N-ethylisoquinolinium bromide- 1-yl group, N-ethylisoquinolinium-1-yl iodide, N-propylisoquinolinium-1-yl chloride, N-propylisoquinolinium-1-yl bromide, iodine N-propylisoquinolinium-1-yl group, chloride N- Tylisoquinolinium-1-yl group, N-butylisoquinolinium-1-yl bromide group, N-butylisoquinolinium-1-yl iodide group, N-methylisoquinolinium chloride 3-yl group, N-methylisoquinolinium-3-yl bromide group, N-methylisoquinolinium-3-yl iodide, N-ethylisoquinolinium-3-yl chloride group, odor N-ethylisoquinolinium-3-yl iodide, N-ethylisoquinolinium-3-yl iodide, N-propylisoquinolinium-3-yl chloride, N-propylisoquinone bromide Norinium-3-yl group, N-propylisoquinolinium-3-yl iodide, N-butylisoquinolinium-3-yl chloride group, N-butylisoquinolinium-3-yl bromide Group, N-butylisoquinolinium-3-yl iodide group N-methylisoquinolinium-4-yl chloride, N-methylisoquinolinium-4-yl bromide, N-methylisoquinolinium-4-yl iodide, N-ethylisoquinone chloride Norinium-4-yl group, N-ethylisoquinolinium-4-yl bromide group, N-ethylisoquinolinium-4-yl iodide, N-propylisoquinolinium-4-yl chloride Group, N-propylisoquinolinium-4-yl bromide group, N-propylisoquinolinium-4-yl iodide group, N-butylisoquinolinium-4-yl chloride group, N-bromide group Butylisoquinolinium-4-yl group, N-butylisoquinolinium-4-yl iodide, N-methylisoquinolinium-5-yl chloride, N-methylisoquinolinium bromide 5-yl group, N-methylisoquinolinium-5 iodide -Yl group, N-ethylisoquinolinium-5-yl chloride, N-ethylisoquinolinium-5-yl bromide, N-ethylisoquinolinium-5-yl iodide, N chloride -Propylisoquinolinium-5-yl group, N-propylisoquinolinium-5-yl group bromide, N-propylisoquinolinium-5-yl iodide, N-butylisoquinolinium chloride -5-yl group, N-butylisoquinolinium-5-yl bromide group, N-butylisoquinolinium-5-yl iodide, N-methylisoquinolinium-6-yl chloride group, N-methylisoquinolinium-6-yl bromide, N-methylisoquinolinium-6-yl iodide, N-ethylisoquinolinium-6-yl chloride, N-ethylisobromide Quinolinium-6-yl group, N-ethylisoquinoyl iodide Um-6-yl group, N-propylisoquinolinium-6-yl chloride, N-propylisoquinolinium-6-yl bromide, N-propylisoquinolinium-6-yl iodide N-butylisoquinolinium-6-yl chloride, N-butylisoquinolinium-6-yl bromide, N-butylisoquinolinium-6-yl iodide, N-methylisochloride Quinolinium-7-yl group, N-methylisoquinolinium-7-yl bromide group, N-methylisoquinolinium-7-yl iodide group, N-ethylisoquinolinium chloride-7- Yl group, N-ethylisoquinolinium-7-yl bromide, N-ethylisoquinolinium-7-yl iodide, N-propylisoquinolinium-7-yl chloride, N-bromide -Propylisoquinolinium-7-yl group, N-iodide Pyrisoquinolinium-7-yl group, N-butylisoquinolinium-7-yl group chloride, N-butylisoquinolinium-7-yl bromide group, N-butylisoquinolinium iodide- 7-yl group, N-methylisoquinolinium-8-yl chloride, N-methylisoquinolinium-8-yl bromide, N-methylisoquinolinium-8-yl iodide, chloride N-ethylisoquinolinium-8-yl group, N-ethylisoquinolinium-8-yl bromide group, N-ethylisoquinolinium-8-yl iodide group, N-propylisoquinolyl chloride Ni-8-yl group, N-propylisoquinolinium-8-yl bromide group, N-propylisoquinolinium-8-yl iodide group, N-butylisoquinolinium-8-yl chloride group N-butylisoquinolinium-8-yl bromide group, Examples thereof include N-butylisoquinolinium-8-yl group, but are not necessarily limited to the groups exemplified here, and the heterocyclic aromatic quaternary ammonium ion represented by the general formula (15) If it is a group derived from it, there is no problem. The alkyl groups such as propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group and the like exemplified here are not limited to linear n-forms, but are isoforms, sec-forms, tert-forms. It may be branched or cyclic like a body.

  Further, in the groups derived from the quaternary ammonium ions represented by the general formulas (11) to (15), various halide ions which are counter anions of the various groups described above include, for example, carbonate ions, nitrate ions, sulfuric acid, and the like. Ion, phosphate ion, borate ion, formate ion, carboxylate ion such as acetate ion, organic acid ion such as sulfonate ion such as trifluoromethanesulfonate ion, p-toluenesulfonate ion, mono or dialkyl phosphate ion Also included are those in which counter anions such as mono or dialkyl borate ions are replaced.

  There is no limitation on the synthesis method of the silica catalyst surface-modified with a tertiary amine group or a quaternary ammonium ionic group used in the present invention. For example, J. Am. Chem. Soc. 127, 530 (2005) document What is necessary is just to synthesize | combine suitably by conventional methods, such as the method described. More specifically, for example, the silicon-containing compound represented by the above general formula (3) and silica are refluxed in a solvent that does not adversely influence the reaction of raw materials and products such as benzene, toluene, dichloromethane, and chloroform. The reaction solution is filtered and the silica is collected by filtration, and the resulting silica is washed with a suitable solvent and dried to give a tertiary amine group or a second group. Silica catalysts surface modified with quaternary ammonium ionic groups can be synthesized.

  As the silicon-containing compound represented by the general formula (3), a commercially available compound or a compound synthesized by a conventional method may be appropriately used. Specifically, for example, when synthesizing a silicon-containing compound in which Y in the general formula (3) is a tertiary amine-derived group, for example, commercially available acetoxyalkyltrimethoxysilane, halogenated alkyltrimethoxysilane, halogen An acyclic tertiary amino group represented by the general formula (7) or a general formula (7) for a compound having a leaving group such as a halogenated aryltrimethoxysilane, acetoxyaralkyltrimethoxysilane, or a halogenated aralkyltrimethoxysilane. The amine corresponding to the heterocyclic non-aromatic tertiary amino group represented by 8) may be appropriately carried out by a conventional method such as reacting in the presence of a palladium catalyst or the like if necessary. When synthesizing a silicon-containing compound in which Y in (3) is a group derived from a quaternary ammonium ion, for example, a commercially available dialkyl amine is used. Alkyl halides are allowed to react with silicon-containing compounds containing groups derived from tertiary amines such as noalkyltrimethoxysilane and silicon-containing compounds obtained by the above synthesis methods (for example, Organometallics 17,3670 (1998)). Or the like).

The silicon-containing compound represented by the general formula (3) thus obtained is at least one reactive group capable of reacting with silica, that is, a group represented by Z in the general formula (3) or Z And a group represented by R ⁴ , the group represented by Z is a reactive group as used herein, and the two groups represented by R ⁴ are each independently a reactive group as used herein. It may mean that it may be a reactive group.

  As a main example of such a silicon-containing compound represented by the general formula (3), as a specific example in the case where Y in the general formula (3) is an acyclic tertiary amino group represented by the general formula (7) For example, dimethylaminomethyltrimethoxysilane, dimethylaminomethyltriethoxysilane, dimethylaminomethyltripropoxysilane, dimethylaminomethyltrichlorosilane, dimethylaminomethyltribromosilane, dimethylaminomethyltriiodosilane, dimethylaminoethyltrimethoxysilane , Dimethylaminopropyltrimethoxysilane, dimethylaminobutyltrimethoxysilane, dimethylaminopentyltrimethoxysilane, dimethylaminohexyltrimethoxysilane, dimethylaminoheptyltrimethoxysilane, dimethylaminooctyl Methoxysilane, diethylaminomethyltrimethoxysilane, diethylaminoethyltrimethoxysilane, diethylaminopropyltrimethoxysilane, diethylaminobutyltrimethoxysilane, diethylaminopentyltrimethoxysilane, diethylaminohexyltrimethoxysilane, diethylaminoheptyltrimethoxysilane, diethylaminooctyltrimethoxysilane , Dipropylaminomethyltrimethoxysilane, dipropylaminoethyltrimethoxysilane, dipropylaminopropyltrimethoxysilane, dipropylaminobutyltrimethoxysilane, dipropylaminopentyltrimethoxysilane, dipropylaminohexyltrimethoxysilane, di Propylaminoheptyltrimethoxysilane, dipropylamino Cutyltrimethoxysilane, dibutylaminomethyltrimethoxysilane, dibutylaminoethyltrimethoxysilane, dibutylaminopropyltrimethoxysilane, dibutylaminobutyltrimethoxysilane, dibutylaminopentyltrimethoxysilane, dibutylaminohexyltrimethoxysilane, dibutylaminoheptyl Trimethoxysilane, dibutylaminooctyltrimethoxysilane, ethylmethylaminomethyltrimethoxysilane, ethylmethylaminoethyltrimethoxysilane, ethylmethylaminopropyltrimethoxysilane, ethylmethylaminobutyltrimethoxysilane, methylpropylaminomethyltrimethoxysilane , Methylpropylaminoethyltrimethoxysilane, methylpropylaminopropyltrimethoxy Silane, methylpropylaminobutyltrimethoxysilane, butylmethylaminomethyltrimethoxysilane, butylmethylaminoethyltrimethoxysilane, butylmethylaminopropyltrimethoxysilane, butylmethylaminobutyltrimethoxysilane, ethylpropylaminomethyltrimethoxysilane, Ethylpropylaminoethyltrimethoxysilane, ethylpropylaminopropyltrimethoxysilane, ethylpropylaminobutyltrimethoxysilane, butylethylaminomethyltrimethoxysilane, butylethylaminoethyltrimethoxysilane, butylethylaminopropyltrimethoxysilane, butylethyl Aminobutyltrimethoxysilane, butylpropylaminomethyltrimethoxysilane, butylpropylaminoethyl Trimethoxysilane, butylpropylaminopropyltrimethoxysilane, butylpropylaminobutyltrimethoxysilane, methylphenylaminomethyltrimethoxysilane, methylphenylaminoethyltrimethoxysilane, methylphenylaminopropyltrimethoxysilane, methylphenylaminobutyltrimethoxy Silane, ethylphenylaminomethyltrimethoxysilane, ethylphenylaminoethyltrimethoxysilane, ethylphenylaminopropyltrimethoxysilane, ethylphenylaminobutyltrimethoxysilane, diphenylaminomethyltrimethoxysilane, diphenylaminoethyltrimethoxysilane, diphenylamino Propyltrimethoxysilane, diphenylaminobutyltrimethoxysilane, dinaphthy Aminomethyltrimethoxysilane, dinaphthylaminoethyltrimethoxysilane, dinaphthylaminopropyltrimethoxysilane, dinaphthylaminobutyltrimethoxysilane, benzylmethylaminomethyltrimethoxysilane, benzylmethylaminoethyltrimethoxysilane, benzylmethylaminopropyl Trimethoxysilane, benzylmethylaminobutyltrimethoxysilane, benzylethylaminomethyltrimethoxysilane, benzylethylaminoethyltrimethoxysilane, benzylethylaminopropyltrimethoxysilane, benzylethylaminobutyltrimethoxysilane, dibenzylaminomethyltrimethoxy Silane, dibenzylaminoethyltrimethoxysilane, dibenzylaminopropyltrimethoxysilane, diben Dilaminobutyltrimethoxysilane, diphenethylaminomethyltrimethoxysilane, diphenethylaminoethyltrimethoxysilane, diphenethylaminopropyltrimethoxysilane, diphenethylaminobutyltrimethoxysilane, dimethylaminophenyltrimethoxysilane, diethylaminophenyltrimethoxy Silane, dipropylaminophenyltrimethoxysilane, dibutylaminophenyltrimethoxysilane, ethylmethylaminophenyltrimethoxysilane, methylpropylaminophenyltrimethoxysilane, butylmethylaminophenyltrimethoxysilane, ethylpropylaminophenyltrimethoxysilane, butyl Ethylaminophenyltrimethoxysilane, butylpropylaminophenyltrimethoxysilane, Phenylaminophenyltrimethoxysilane, dinaphthylaminophenyltrimethoxysilane, dibenzylaminophenyltrimethoxysilane, diphenethylaminophenyltrimethoxysilane, dimethylaminobenzyltrimethoxysilane, diethylaminobenzyltrimethoxysilane, dipropylaminobenzyltrimethoxy Silane, dibutylaminobenzyltrimethoxysilane, ethylmethylaminobenzyltrimethoxysilane, methylpropylaminobenzyltrimethoxysilane, butylmethylaminobenzyltrimethoxysilane, ethylpropylaminobenzyltrimethoxysilane, butylethylaminobenzyltrimethoxysilane, butyl Propylaminobenzyltrimethoxysilane, diphenylaminobenzyltrimethoxy Orchid, dinaphthylaminobenzyltrimethoxysilane, dibenzylaminobenzyltrimethoxysilane, diphenethylaminobenzyltrimethoxysilane, and the like, but are not necessarily limited to the silicon-containing compounds exemplified here, and the general formula (3) If Y in is an acyclic tertiary amino group represented by the general formula (7), there is no problem. The alkyl groups such as propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group and the like exemplified here are not limited to linear n-forms, but are isoforms, sec-forms, tert-forms. It may be branched or cyclic like a body.

  Specific examples of the silicon-containing compound when Y in the general formula (3) is a heterocyclic non-aromatic tertiary amino group represented by the general formula (8) include, for example, 1-pyrrolidinomethyltrimethoxysilane 1-pyrrolidinomethyltriethoxysilane, 1-pyrrolidinomethyltripropoxysilane, 1-pyrrolidinomethyltrichlorosilane, 1-pyrrolidinomethyltribromosilane, 1-pyrrolidinomethyltriiodosilane, 1-pyrrolidinoethyl Trimethoxysilane, 1-pyrrolidinopropyltrimethoxysilane, 1-pyrrolidinobutyltrimethoxysilane, 1-pyrrolidinopentyltrimethoxysilane, 1-pyrrolidinohexyltrimethoxysilane, 1-pyrrolidinoheptyltrimethoxysilane, 1 -Pyrrolidinooctyltrimethoxysilane, 1-piperidi Methyltrimethoxysilane, 1-piperidinoethyltrimethoxysilane, 1-piperidinopropyltrimethoxysilane, 1-piperidinobutyltrimethoxysilane, 1-piperidinopentyltrimethoxysilane, 1-piperidino Hexyltrimethoxysilane, 1-piperidinoheptyltrimethoxysilane, 1-piperidinooctyltrimethoxysilane, 1-pyrrolylmethyltrimethoxysilane, 1-pyrrolylethyltrimethoxysilane, 1-pyrrolylpropyltrimethoxy Silane, 1-pyrrolylbutyltrimethoxysilane, 1-pyrrolylpentyltrimethoxysilane, 1-pyrrolylhexyltrimethoxysilane, 1-pyrrolylheptyltrimethoxysilane, 1-pyrrolyloctyltrimethoxysilane, 2,3- Dihydro-1H-1-pyrrole Methyltrimethoxysilane, 2,3-dihydro-1H-1-pyrrolylethyltrimethoxysilane, 2,3-dihydro-1H-1-pyrrolylpropyltrimethoxysilane, 2,3-dihydro-1H-1-pyrrole Rubutyltrimethoxysilane, 2,5-dihydro-1H-1-pyrrolylmethyltrimethoxysilane, 2,5-dihydro-1H-1-pyrrolylethyltrimethoxysilane, 2,5-dihydro-1H-1- Pyrrolylpropyltrimethoxysilane, 2,5-dihydro-1H-1-pyrrolylbutyltrimethoxysilane, 1,2,3,4-tetrahydro-1-pyridylmethyltrimethoxysilane, 1,2,3,4 Tetrahydro-1-pyridylethyltrimethoxysilane, 1,2,3,4-tetrahydro-1-pyridylpropyltrimethoxysila 1,2,3,4-tetrahydro-1-pyridylbutyltrimethoxysilane, 1,2,5,6-tetrahydro-1-pyridylmethyltrimethoxysilane, 1,2,5,6-tetrahydro-1- Pyridylethyltrimethoxysilane, 1,2,5,6-tetrahydro-1-pyridylpropyltrimethoxysilane, 1,2,5,6-tetrahydro-1-pyridylbutyltrimethoxysilane, 1,2-dihydro-1- Pyridylmethyltrimethoxysilane, 1,2-dihydro-1-pyridylethyltrimethoxysilane, 1,2-dihydro-1-pyridylpropyltrimethoxysilane, 1,2-dihydro-1-pyridylbutyltrimethoxysilane, 1H, 3H-1-pyridylmethyltrimethoxysilane, 1H, 3H-1-pyridylethyltrimethoxysilane 1H, 3H-1-pyridylpropyltrimethoxysilane, 1H, 3H-1-pyridylbutyltrimethoxysilane, 1-pyrrolidinophenyltrimethoxysilane, 1-piperidinophenyltrimethoxysilane, 1-pyrrolylphenyl Trimethoxysilane, 2,3-dihydro-1H-1-pyrrolylphenyltrimethoxysilane, 2,5-dihydro-1H-1-pyrrolylphenyltrimethoxysilane, 1,2,3,4-tetrahydro-1- Pyridylphenyltrimethoxysilane, 1,2,5,6-tetrahydro-1-pyridylphenyltrimethoxysilane, 1,2-dihydro-1-pyridylphenyltrimethoxysilane, 1H, 3H-1-pyridylphenyltrimethoxysilane, 1-pyrrolidinobenzyltrimethoxysilane, 1-piperidino Benzyltrimethoxysilane, 1-pyrrolylbenzyltrimethoxysilane, 2,3-dihydro-1H-1-pyrrolylbenzyltrimethoxysilane, 2,5-dihydro-1H-1-pyrrolylbenzyltrimethoxysilane, 1 , 2,3,4-tetrahydro-1-pyridylbenzyltrimethoxysilane, 1,2,5,6-tetrahydro-1-pyridylbenzyltrimethoxysilane, 1,2-dihydro-1-pyridylbenzyltrimethoxysilane, 1H , 3H-1-pyridylbenzyltrimethoxysilane and the like, but are not necessarily limited to the silicon-containing compounds exemplified here, and Y in the general formula (3) is a heterocyclic non-cyclic compound represented by the general formula (8). Any aromatic tertiary amino group can be used. The alkyl groups such as propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group and the like exemplified here are not limited to linear n-forms, but are isoforms, sec-forms, tert-forms. It may be branched or cyclic like a body.

  Furthermore, specific examples of the silicon-containing compound when Y in the general formula (3) is a group derived from a heterocyclic aromatic tertiary amine represented by the general formula (9) include, for example, 2-pyridyltrimethoxysilane, 2-pyridyltriethoxysilane, 2-pyridyltripropoxysilane, 2-pyridyltrichlorosilane, 2-pyridyltribromosilane, 2-pyridyltriiodosilane, 2-pyridylmethyltrimethoxysilane, 2-pyridylethyltrimethoxysilane, 2-pyridylpropyltrimethoxysilane, 2-pyridylbutyltrimethoxysilane, 2-pyridylpentyltrimethoxysilane, 2-pyridylhexyltrimethoxysilane, 2-pyridylheptyltrimethoxysilane, 2-pyridyloctyltrimethoxysilane, 3- Pyridyltrimethoxysilane 3-pyridylmethyltrimethoxysilane, 3-pyridylethyltrimethoxysilane, 3-pyridylpropyltrimethoxysilane, 3-pyridylbutyltrimethoxysilane, 3-pyridylpentyltrimethoxysilane, 3-pyridylhexyltrimethoxysilane, 3- Pyridylheptyltrimethoxysilane, 3-pyridyloctyltrimethoxysilane, 4-pyridyltrimethoxysilane, 4-pyridylmethyltrimethoxysilane, 4-pyridylethyltrimethoxysilane, 4-pyridylpropyltrimethoxysilane, 4-pyridylbutyltri Methoxysilane, 4-pyridylpentyltrimethoxysilane, 4-pyridylhexyltrimethoxysilane, 4-pyridylheptyltrimethoxysilane, 4-pyridyloctyltrimethoxysilane, 2- Noryltrimethoxysilane, 2-quinolylmethyltrimethoxysilane, 2-quinolylethyltrimethoxysilane, 2-quinolylpropyltrimethoxysilane, 2-quinolylbutyltrimethoxysilane, 2-quinolylpentyltrimethoxysilane, 2-quinolylhexyltrimethoxysilane, 2-quinolylheptyltrimethoxysilane, 2-quinolyloctyltrimethoxysilane, 3-quinolyltrimethoxysilane, 3-quinolylmethyltrimethoxysilane, 3-quinolylethyltri Methoxysilane, 3-quinolylpropyltrimethoxysilane, 3-quinolylbutyltrimethoxysilane, 3-quinolylpentyltrimethoxysilane, 3-quinolylhexyltrimethoxysilane, 3-quinolylheptyltrimethoxysilane, 3- Quinolyl Octyl Trimethoxysilane, 4-quinolyltrimethoxysilane, 4-quinolylmethyltrimethoxysilane, 4-quinolylethyltrimethoxysilane, 4-quinolylpropyltrimethoxysilane, 4-quinolylbutyltrimethoxysilane, 4- Quinolylpentyltrimethoxysilane, 4-quinolylhexyltrimethoxysilane, 4-quinolylheptyltrimethoxysilane, 4-quinolyloctyltrimethoxysilane, 5-quinolyltrimethoxysilane, 5-quinolylmethyltrimethoxysilane 5-quinolylethyltrimethoxysilane, 5-quinolylpropyltrimethoxysilane, 5-quinolylbutyltrimethoxysilane, 5-quinolylpentyltrimethoxysilane, 5-quinolylhexyltrimethoxysilane, 5-quinolyl Heptyltrimethoxy , 5-quinolyloctyltrimethoxysilane, 6-quinolyltrimethoxysilane, 6-quinolylmethyltrimethoxysilane, 6-quinolylethyltrimethoxysilane, 6-quinolylpropyltrimethoxysilane, 6-quinolyl Butyltrimethoxysilane, 6-quinolylpentyltrimethoxysilane, 6-quinolylhexyltrimethoxysilane, 6-quinolylheptyltrimethoxysilane, 6-quinolyloctyltrimethoxysilane, 7-quinolyltrimethoxysilane, 7 -Quinolylmethyltrimethoxysilane, 7-quinolylethyltrimethoxysilane, 7-quinolylpropyltrimethoxysilane, 7-quinolylbutyltrimethoxysilane, 7-quinolylpentyltrimethoxysilane, 7-quinolylhexyltri Methoxysilane, 7-quino Ruheptyltrimethoxysilane, 7-quinolyloctyltrimethoxysilane, 8-quinolyltrimethoxysilane, 8-quinolylmethyltrimethoxysilane, 8-quinolylethyltrimethoxysilane, 8-quinolylpropyltrimethoxysilane, 8-quinolylbutyltrimethoxysilane, 8-quinolylpentyltrimethoxysilane, 8-quinolylhexyltrimethoxysilane, 8-quinolylheptyltrimethoxysilane, 8-quinolyloctyltrimethoxysilane, 1-isoquinolyl Trimethoxysilane, 1-isoquinolylmethyltrimethoxysilane, 1-isoquinolylethyltrimethoxysilane, 1-isoquinolylpropyltrimethoxysilane, 1-isoquinolylbutyltrimethoxysilane, 1-isoquinolylpentyl Trimethoxysilane, 1-isoquinolylhexyltrimethoxysilane, 1-isoquinolylheptyltrimethoxysilane, 1-isoquinolyloctyltrimethoxysilane, 3-isoquinolyltrimethoxysilane, 3-isoquinolylmethyltrimethoxysilane, 3 -Isoquinolylethyltrimethoxysilane, 3-isoquinolylpropyltrimethoxysilane, 3-isoquinolylbutyltrimethoxysilane, 3-isoquinolylpentyltrimethoxysilane, 3-isoquinolylhexyltrimethoxysilane, 3 -Isoquinolyl heptyltrimethoxysilane, 3-isoquinolyloctyltrimethoxysilane, 4-isoquinolyltrimethoxysilane, 4-isoquinolylmethyltrimethoxysilane, 4-isoquinolylethyltrimethoxysilane, 4- Isoquinolylpropyltrimeth Sisilane, 4-isoquinolylbutyltrimethoxysilane, 4-isoquinolylpentyltrimethoxysilane, 4-isoquinolylhexyltrimethoxysilane, 4-isoquinolylheptyltrimethoxysilane, 4-isoquinolyloctyltrimethoxy Silane, 5-isoquinolyltrimethoxysilane, 5-isoquinolylmethyltrimethoxysilane, 5-isoquinolylethyltrimethoxysilane, 5-isoquinolylpropyltrimethoxysilane, 5-isoquinolylbutyltrimethoxysilane 5-isoquinolylpentyltrimethoxysilane, 5-isoquinolylhexyltrimethoxysilane, 5-isoquinolylheptyltrimethoxysilane, 5-isoquinolyloctyltrimethoxysilane, 6-isoquinolyltrimethoxysilane, 6-Isoquinolylme Rutrimethoxysilane, 6-isoquinolylethyltrimethoxysilane, 6-isoquinolylpropyltrimethoxysilane, 6-isoquinolylbutyltrimethoxysilane, 6-isoquinolylpentyltrimethoxysilane, 6-isoquinolylhexyl Trimethoxysilane, 6-isoquinolylheptyltrimethoxysilane, 6-isoquinolyloctyltrimethoxysilane, 7-isoquinolyltrimethoxysilane, 7-isoquinolylmethyltrimethoxysilane, 7-isoquinolylethyltri Methoxysilane, 7-isoquinolylpropyltrimethoxysilane, 7-isoquinolylbutyltrimethoxysilane, 7-isoquinolylpentyltrimethoxysilane, 7-isoquinolylhexyltrimethoxysilane, 7-isoquinolylheptyltri Methoxysilane, 7 -Isoquinolyloctyltrimethoxysilane, 8-isoquinolyltrimethoxysilane, 8-isoquinolylmethyltrimethoxysilane, 8-isoquinolylethyltrimethoxysilane, 8-isoquinolylpropyltrimethoxysilane, 8- Isoquinolylbutyltrimethoxysilane, 8-isoquinolylpentyltrimethoxysilane, 8-isoquinolylhexyltrimethoxysilane, 8-isoquinolylheptyltrimethoxysilane, 8-isoquinolyloctyltrimethoxysilane, 2- Pyridylphenyltrimethoxysilane, 3-pyridylphenyltrimethoxysilane, 4-pyridylphenyltrimethoxysilane, 2-quinolylphenyltrimethoxysilane, 3-quinolylphenyltrimethoxysilane, 4-quinolylphenyltrimethoxysilane, 5 Quinolylphenyltrimethoxysilane, 6-quinolylphenyltrimethoxysilane, 7-quinolylphenyltrimethoxysilane, 8-quinolylphenyltrimethoxysilane, 1-isoquinolylphenyltrimethoxysilane, 3-isoquinolylphenyl Trimethoxysilane, 4-isoquinolylphenyltrimethoxysilane, 5-isoquinolylphenyltrimethoxysilane, 6-isoquinolylphenyltrimethoxysilane, 7-isoquinolylphenyltrimethoxysilane, 8-isoquinolylphenyl Trimethoxysilane, 2-pyridylbenzyltrimethoxysilane, 3-pyridylbenzyltrimethoxysilane, 4-pyridylbenzyltrimethoxysilane, 2-quinolylbenzyltrimethoxysilane, 3-quinolylbenzyltrimethoxysilane, -Quinolylbenzyltrimethoxysilane, 5-quinolylbenzyltrimethoxysilane, 6-quinolylbenzyltrimethoxysilane, 7-quinolylbenzyltrimethoxysilane, 8-quinolylbenzyltrimethoxysilane, 1-isoquinolylbenzyl Trimethoxysilane, 3-isoquinolylbenzyltrimethoxysilane, 4-isoquinolylbenzyltrimethoxysilane, 5-isoquinolylbenzyltrimethoxysilane, 6-isoquinolylbenzyltrimethoxysilane, 7-isoquinolylbenzyl Examples include trimethoxysilane, 8-isoquinolylbenzyltrimethoxysilane, and the like, but are not necessarily limited to the silicon-containing compounds exemplified here. Y in the general formula (3) is a complex represented by the general formula (9). In the case of radicals derived from cyclic aromatic tertiary amines If so, there is no problem. The alkyl groups such as propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group and the like exemplified here are not limited to linear n-forms, but are isoforms, sec-forms, tert-forms. It may be branched or cyclic like a body.

Furthermore, specific examples of the silicon-containing compound when Y in the general formula (3) is a group derived from a heterocyclic non-aromatic tertiary amine represented by the general formula (10) include, for example, N-methyl-2 -Pyrrolidinyltrimethoxysilane, N-methyl-2-pyrrolidinyltriethoxysilane, N-methyl-2-pyrrolidinyltripropoxysilane, N-methyl-2-pyrrolidinyltrichlorosilane, N-methyl-2-pyrrolidini Rutribromosilane, N-methyl-2-pyrrolidinyltriiodosilane, N-methyl-2-pyrrolidinylmethyltrimethoxysilane, N-methyl-2-pyrrolidinylethyltrimethoxysilane, N-methyl-2- Pyrrolidinylpropyltrimethoxysilane, N-methyl-2-pyrrolidinylbutyltrimethoxysilane, N-methyl-2-pyrrole Nylpentyltrimethoxysilane, N-methyl-2-pyrrolidinylhexyltrimethoxysilane, N-methyl-2-pyrrolidinylheptyltrimethoxysilane, N-methyl-2-pyrrolidinyloctyltrimethoxysilane, N-ethyl 2-pyrrolidinyltrimethoxysilane, N-ethyl-2-pyrrolidinylmethyltrimethoxysilane, N-ethyl-2-pyrrolidinylethyltrimethoxysilane, N-ethyl-2-pyrrolidinylpropyltrimethoxysilane N-ethyl-2-pyrrolidinylbutyltrimethoxysilane, N-propyl-2-pyrrolidinyltrimethoxysilane, N-propyl-2-pyrrolidinylmethyltrimethoxysilane, N-propyl-2-pyrrolidinyl Ethyltrimethoxysilane, N-propyl-2-pyrrolidinylpropylene Trimethoxysilane, N-propyl-2-pyrrolidinylbutyltrimethoxysilane, N-butyl-2-pyrrolidinyltrimethoxysilane, N-butyl-2-pyrrolidinylmethyltrimethoxysilane, N-butyl-2- Pyrrolidinylethyltrimethoxysilane, N-butyl-2-pyrrolidinylpropyltrimethoxysilane, N-butyl-2-pyrrolidinylbutyltrimethoxysilane, N-pentyl-2-pyrrolidinyltrimethoxysilane, N- Pentyl-2-pyrrolidinylmethyltrimethoxysilane, N-pentyl-2-pyrrolidinylethyltrimethoxysilane, N-pentyl-2-pyrrolidinylpropyltrimethoxysilane, N-pentyl-2-pyrrolidinylbutyl Trimethoxysilane, N-hexyl-2-pyrrolidinyltrimethoxysilane N-hexyl-2-pyrrolidinylmethyltrimethoxysilane, N-hexyl-2-pyrrolidinylethyltrimethoxysilane, N-hexyl-2-pyrrolidinylpropyltrimethoxysilane, N-hexyl-2-pyrrole Dinylbutyltrimethoxysilane, N-heptyl-2-pyrrolidinyltrimethoxysilane, N-heptyl-2-pyrrolidinylmethyltrimethoxysilane, N-heptyl-2-pyrrolidinylethyltrimethoxysilane, N-heptyl 2-pyrrolidinylpropyltrimethoxysilane, N-heptyl-2-pyrrolidinylbutyltrimethoxysilane, N-octyl-2-pyrrolidinyltrimethoxysilane, N-octyl-2-pyrrolidinylmethyltrimethoxysilane N-octyl-2-pyrrolidinylethyltrimethoxysilane, -Octyl-2-pyrrolidinylpropyltrimethoxysilane, N-octyl-2-pyrrolidinylbutyltrimethoxysilane, N-methyl-3-pyrrolidinyltrimethoxysilane, N-methyl-3-pyrrolidinylmethyltri Methoxysilane, N-methyl-3-pyrrolidinylethyltrimethoxysilane, N-methyl-3-pyrrolidinylpropyltrimethoxysilane, N-methyl-3-pyrrolidinylbutyltrimethoxysilane, N-ethyl-3 -Pyrrolidinyltrimethoxysilane, N-ethyl-3-pyrrolidinylmethyltrimethoxysilane, N-ethyl-3-pyrrolidinylethyltrimethoxysilane, N-ethyl-3-pyrrolidinylpropyltrimethoxysilane, N -Ethyl-3-pyrrolidinylbutyltrimethoxysilane, N-methyl-2-pipe Diltrimethoxysilane, N-methyl-2-piperidylmethyltrimethoxysilane, N-methyl-2-piperidylethyltrimethoxysilane, N-methyl-2-piperidylpropyltrimethoxysilane, N-methyl-2-piperidylbutyltri Methoxysilane, N-ethyl-2-piperidyltrimethoxysilane, N-ethyl-2-piperidylmethyltrimethoxysilane, N-ethyl-2-piperidylethyltrimethoxysilane, N-ethyl-2-piperidylpropyltrimethoxysilane, N-ethyl-2-piperidylbutyltrimethoxysilane, N-methyl-3-piperidyltrimethoxysilane, N-methyl-3-piperidylmethyltrimethoxysilane, N-methyl-3-piperidylethyltrimethoxysilane, N-methyl -3-piperidyl Propyltrimethoxysilane, N-methyl-3-piperidylbutyltrimethoxysilane, N-ethyl-3-piperidyltrimethoxysilane, N-ethyl-3-piperidylmethyltrimethoxysilane, N-ethyl-3-piperidylethyltrimethoxy Silane, N-ethyl-3-piperidylpropyltrimethoxysilane, N-ethyl-3-piperidylbutyltrimethoxysilane, N-methyl-4-piperidyltrimethoxysilane, N-methyl-4-piperidylmethyltrimethoxysilane, N -Methyl-4-piperidylethyltrimethoxysilane, N-methyl-4-piperidylpropyltrimethoxysilane, N-methyl-4-piperidylbutyltrimethoxysilane, N-ethyl-4-piperidyltrimethoxysilane, N-ethyl- 4-piperidylme Rutrimethoxysilane, N-ethyl-4-piperidylethyltrimethoxysilane, N-ethyl-4-piperidylpropyltrimethoxysilane, N-ethyl-4-piperidylbutyltrimethoxysilane, N-methyl-2-pyrrolyltrimethoxysilane N-methyl-2-pyrrolylmethyltrimethoxysilane, N-methyl-2-pyrrolylethyltrimethoxysilane, N-methyl-2-pyrrolylpropyltrimethoxysilane, N-methyl-2-pyrrolylbutyltrimethoxysilane Methoxysilane, N-ethyl-2-pyrrolyltrimethoxysilane, N-ethyl-2-pyrrolylmethyltrimethoxysilane, N-ethyl-2-pyrrolylethyltrimethoxysilane, N-ethyl-2-pyrrolylpropyltri Methoxysilane, N-ethyl-2-pyrrolylbutyltrimethoxy Lan, N-methyl-3-pyrrolyltrimethoxysilane, N-methyl-3-pyrrolylmethyltrimethoxysilane, N-methyl-3-pyrrolylethyltrimethoxysilane, N-methyl-3-pyrrolylpropyltrimethoxy Silane, N-methyl-3-pyrrolylbutyltrimethoxysilane, N-ethyl-3-pyrrolyltrimethoxysilane, N-ethyl-3-pyrrolylmethyltrimethoxysilane, N-ethyl-3-pyrrolylethyltrimethoxy Silane, N-ethyl-3-pyrrolylpropyltrimethoxysilane, N-ethyl-3-pyrrolylbutyltrimethoxysilane, N-methyl-2,3-dihydro-1H-2-pyrrolyltrimethoxysilane, N-methyl -2,3-dihydro-1H-2-pyrrolylmethyltrimethoxysilane, N-methyl-2,3-dihydride B-1H-3-pyrrolyltrimethoxysilane, N-methyl-2,3-dihydro-1H-3-pyrrolylmethyltrimethoxysilane, N-methyl-2,3-dihydro-1H-4-pyrrolyltrimethoxysilane N-methyl-2,3-dihydro-1H-4-pyrrolylmethyltrimethoxysilane, N-methyl-2,3-dihydro-1H-5-pyrrolyltrimethoxysilane, N-methyl-2,3-dihydro -1H-5-pyrrolylmethyltrimethoxysilane, N-methyl-2,5-dihydro-1H-2-pyrrolyltrimethoxysilane, N-methyl-2,5-dihydro-1H-2-pyrrolylmethyltrimethoxy Silane, N-methyl-2,5-dihydro-1H-3-pyrrolyltrimethoxysilane, N-methyl-2,5-dihydro-1H-3-pyrrolylmethyl Methoxysilane, N-methyl-1,2,3,4-tetrahydro-2-pyridyltrimethoxysilane, N-methyl-1,2,3,4-tetrahydro-2-pyridylmethyltrimethoxysilane, N-methyl- 1,2,3,4-tetrahydro-3-pyridylpyridyltrimethoxysilane, N-methyl-1,2,3,4-tetrahydro-3-pyridylmethyltrimethoxysilane, N-methyl-1,2,3 4-tetrahydro-4-pyridyltrimethoxysilane, N-methyl-1,2,3,4-tetrahydro-4-pyridylmethyltrimethoxysilane, N-methyl-1,2,3,4-tetrahydro-5-pyridyl Trimethoxysilane, N-methyl-1,2,3,4-tetrahydro-5-pyridylmethyltrimethoxysilane, N-methyl-1,2,3 -Tetrahydro-6-pyridyltrimethoxysilane, N-methyl-1,2,3,4-tetrahydro-6-pyridylmethyltrimethoxysilane, N-methyl-1,2,5,6-tetrahydro-2-pyridyltri Methoxysilane, N-methyl-1,2,5,6-tetrahydro-2-pyridylmethyltrimethoxysilane, N-methyl-1,2,5,6-tetrahydro-3-pyridyltrimethoxysilane, N-methyl- 1,2,5,6-tetrahydro-3-pyridylmethyltrimethoxysilane, N-methyl-1,2,5,6-tetrahydro-4-pyridyltrimethoxysilane, N-methyl-1,2,5,6 -Tetrahydro-4-pyridylmethyltrimethoxysilane, N-methyl-1,2,5,6-tetrahydro-5-pyridyltrimethoxysilane, N -Methyl-1,2,5,6-tetrahydro-5-pyridylmethyltrimethoxysilane,
N-methyl-1,2,5,6-tetrahydro-6-pyridyltrimethoxysilane, N-methyl-1,2,5,6-tetrahydro-6-pyridylmethyltrimethoxysilane, N-methyl-1,2 -Dihydro-2-pyridyltrimethoxysilane, N-methyl-1,2-dihydro-2-pyridylmethyltrimethoxysilane, N-methyl-1,2-dihydro-3-pyridyltrimethoxysilane, N-methyl-1 , 2-dihydro-3-pyridylmethyltrimethoxysilane, N-methyl-1,2-dihydro-4-pyridyltrimethoxysilane, N-methyl-1,2-dihydro-4-pyridylmethyltrimethoxysilane, N- Methyl-1,2-dihydro-5-pyridyltrimethoxysilane, N-methyl-1,2-dihydro-5-pyridylmethyltrimethoxy Lan, N-methyl-1,2-dihydro-6-pyridyltrimethoxysilane, N-methyl-1,2-dihydro-6-pyridylmethyltrimethoxysilane, N-methyl-1H, 3H-2-pyridyltrimethoxy Silane, N-methyl-1H, 3H-2-pyridylmethyltrimethoxysilane, N-methyl-1H, 3H-3-pyridyltrimethoxysilane, N-methyl-1H, 3H-3-pyridylmethyltrimethoxysilane, N -Methyl-1H, 3H-4-pyridyltrimethoxysilane, N-methyl-1H, 3H-4-pyridylmethyltrimethoxysilane, N-methyl-2-pyrrolidinylphenyltrimethoxysilane, N-ethyl-2- Pyrrolidinylphenyltrimethoxysilane, N-propyl-2-pyrrolidinylphenyltrimethoxysilane, N- Tyl-2-pyrrolidinylphenyltrimethoxysilane, N-pentyl-2-pyrrolidinylphenyltrimethoxysilane, N-hexyl-2-pyrrolidinylphenyltrimethoxysilane, N-heptyl-2-pyrrolidinylphenyl Trimethoxysilane, N-octyl-2-pyrrolidinylphenyltrimethoxysilane, N-methyl-3-pyrrolidinylphenyltrimethoxysilane, N-ethyl-3-pyrrolidinylphenyltrimethoxysilane, N-propyl- 3-pyrrolidinylphenyltrimethoxysilane, N-butyl-3-pyrrolidinylphenyltrimethoxysilane, N-methyl-2-piperidylphenyltrimethoxysilane, N-ethyl-2-piperidylphenyltrimethoxysilane, N- Propyl-2-piperidylphenyl trimethoxy Orchid, N-butyl-2-piperidylphenyltrimethoxysilane, N-methyl-3-piperidylphenyltrimethoxysilane, N-ethyl-3-piperidylphenyltrimethoxysilane, N-propyl-3-piperidylphenyltrimethoxysilane, N-butyl-3-piperidylphenyltrimethoxysilane, N-methyl-4-piperidylphenyltrimethoxysilane, N-ethyl-4-piperidylphenyltrimethoxysilane, N-propyl-4-piperidylphenyltrimethoxysilane, N- Butyl-4-piperidylphenyltrimethoxysilane, N-methyl-2-pyrrolylphenyltrimethoxysilane, N-ethyl-2-pyrrolylphenyltrimethoxysilane, N-propyl-2-pyrrolylphenyltrimethoxysilane, N -Butyl- -Pyrrolylphenyltrimethoxysilane, N-methyl-3-pyrrolylphenyltrimethoxysilane, N-ethyl-3-pyrrolylphenyltrimethoxysilane, N-propyl-3-pyrrolylphenyltrimethoxysilane, N-butyl -3-pyrrolylphenyltrimethoxysilane, N-methyl-2-pyrrolidinylbenzyltrimethoxysilane, N-ethyl-2-pyrrolidinylbenzyltrimethoxysilane, N-propyl-2-pyrrolidinylbenzyltrimethoxy Silane, N-butyl-2-pyrrolidinylbenzyltrimethoxysilane, N-pentyl-2-pyrrolidinylbenzyltrimethoxysilane, N-hexyl-2-pyrrolidinylbenzyltrimethoxysilane, N-heptyl-2- Pyrrolidinylbenzyltrimethoxysilane, N-octyl-2 Pyrrolidinylbenzyltrimethoxysilane, N-methyl-3-pyrrolidinylbenzyltrimethoxysilane, N-ethyl-3-pyrrolidinylbenzyltrimethoxysilane, N-propyl-3-pyrrolidinylbenzyltrimethoxysilane, N-butyl-3-pyrrolidinylbenzyltrimethoxysilane, N-methyl-2-piperidylbenzyltrimethoxysilane, N-ethyl-2-piperidylbenzyltrimethoxysilane, N-propyl-2-piperidylbenzyltrimethoxysilane, N-butyl-2-piperidylbenzyltrimethoxysilane, N-methyl-3-piperidylbenzyltrimethoxysilane, N-ethyl-3-piperidylbenzyltrimethoxysilane, N-propyl-3-piperidylbenzyltrimethoxysilane, N- Butyl-3-pi Peridylbenzyltrimethoxysilane, N-methyl-4-piperidylbenzyltrimethoxysilane, N-ethyl-4-piperidylbenzyltrimethoxysilane, N-propyl-4-piperidylbenzyltrimethoxysilane, N-butyl-4-piperidyl Benzyltrimethoxysilane, N-methyl-2-pyrrolylbenzyltrimethoxysilane, N-ethyl-2-pyrrolylbenzyltrimethoxysilane, N-propyl-2-pyrrolylbenzyltrimethoxysilane, N-butyl-2- Pyrrolylbenzyltrimethoxysilane, N-methyl-3-pyrrolylbenzyltrimethoxysilane, N-ethyl-3-pyrrolylbenzyltrimethoxysilane, N-propyl-3-pyrrolylbenzyltrimethoxysilane, N-butyl- 3-pyrrolylbenzyltrimethoxy Or the like, but is not necessarily limited to the silicon-containing compounds exemplified here, Y in the general formula (3) is a group derived from a heterocyclic non-aromatic tertiary amine represented by the general formula (10) If this is the case, it does not matter. The alkyl groups such as propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group and the like exemplified here are not limited to linear n-forms, but are isoforms, sec-forms, tert-forms. It may be branched or cyclic like a body.

Specific examples of the silicon-containing compound when Y in the general formula (3) is an acyclic quaternary ammonio group represented by the general formula (11) include, for example, tetramethylammonium trimethoxysilane fluoride, tetrachloride chloride Methylammonium trimethoxysilane, tetramethylammonium trimethoxysilane bromide, tetramethylammonium trimethoxysilane iodide, tetramethylammonium triethoxysilane fluoride, tetramethylammonium triethoxysilane chloride, tetramethylammonium triethoxysilane bromide, Tetramethylammonium triethoxysilane, tetramethylammonium tripropoxysilane fluoride, tetramethylammonium tripropoxysilane chloride, tetramethylammonium tripropoxysilane bromide Tetramethylammonium tripropoxysilane, tetramethylammonium trichlorosilane fluoride, tetramethylammonium trichlorosilane chloride, tetramethylammonium trichlorosilane bromide, tetramethylammonium trichlorosilane iodide, tetramethylammonium tribromosilane fluoride, chloride Tetramethylammonium tribromosilane, tetramethylammonium tribromosilane, tetramethylammonium tribromosilane iodide, tetramethylammonium triiodosilane fluoride, tetramethylammonium triiodosilane chloride, tetramethylammonium triiodosilane bromide , Tetramethylammonium triiodosilane iodide, tetraethylammonium trimethoxysilane chloride, Tetraethylammonium trimethoxysilane, tetraethylammonium trimethoxysilane iodide, tetrapropylammonium trimethoxysilane chloride, tetrapropylammonium trimethoxysilane bromide, tetrapropylammonium trimethoxysilane iodide, tetrabutylammonium trimethoxysilane chloride, odor Tetrabutylammonium trimethoxysilane, tetrabutylammonium trimethoxysilane iodide, tetrapentylammonium trimethoxysilane chloride, tetrapentylammonium trimethoxysilane bromide, tetrapentylammonium trimethoxysilane iodide, tetrahexylammonium trimethoxysilane chloride , Tetrahexylammonium bromide trimethoxysilane, tetrahexyl iodide Ammonium trimethoxysilane, tetraheptylammonium chloride trimethoxysilane, tetraheptylammonium trimethoxysilane bromide, tetraheptylammonium trimethoxysilane iodide, tetraoctylammonium trimethoxysilane chloride, tetraoctylammonium trimethoxysilane bromide, iodide Tetraoctylammonium trimethoxysilane, trimethylethylammonium trimethoxysilane chloride, trimethylethylammonium trimethoxysilane bromide, trimethylethylammonium trimethoxysilane iodide, trimethylpropylammonium trimethoxysilane chloride, trimethylpropylammonium trimethoxysilane bromide, Trimethylpropylammonium trimethoxysilane, trichloride chloride Tylbutylammonium trimethoxysilane, trimethylbutylammonium trimethoxysilane bromide, trimethylbutylammonium trimethoxysilane iodide, trimethylpentylammonium trimethoxysilane chloride, trimethylpentylammonium bromide trimethoxysilane, trimethylpentylammonium trimethoxysilane iodide , Trimethylhexylammonium trimethoxysilane chloride, trimethylhexylammonium bromide trimethoxysilane, trimethylhexylammonium trimethoxysilane iodide, trimethylheptylammonium trimethoxysilane chloride, trimethylheptylammonium trimethoxysilane bromide, trimethylheptylammonium iodide trimethylsilane Methoxysilane, trimethyloctyl chloride Monium trimethoxysilane, trimethyloctylammonium bromide trimethoxysilane, trimethyloctylammonium iodide trimethoxysilane, triethylmethylammonium trimethoxysilane chloride, triethylmethylammonium trimethoxysilane bromide, triethylmethylammonium trimethoxysilane iodide, chloride Triethylpropylammonium trimethoxysilane, triethylpropylammonium trimethoxysilane bromide, triethylpropylammonium trimethoxysilane iodide, triethylbutylammonium trimethoxysilane chloride, triethylbutylammonium bromide trimethoxysilane, triethylbutylammonium trimethoxysilane iodide , Triethylpentylammonium chloride trimethoxysilane Run, triethylpentylammonium bromide trimethoxysilane, triethylpentylammonium iodide trimethoxysilane, triethylhexylammonium chloride trimethoxysilane, triethylhexylammonium bromide trimethoxysilane, triethylhexylammonium bromide trimethoxysilane, triethylheptylammonium chloride Trimethoxysilane, triethylheptylammonium bromide trimethoxysilane, triethylheptylammonium iodide trimethoxysilane, triethyloctylammonium trimethoxysilane chloride, triethyloctylammonium bromide trimethoxysilane, triethyloctylammonium iodide trimethoxysilane, diethyl chloride Dimethylammonium trimethoxysilane, dibromide Tildimethylammonium trimethoxysilane, diethyldimethylammonium trimethoxysilane, ethyldimethylpropylammonium trimethoxysilane, ethyldimethylpropylammonium trimethoxysilane, ethyldimethylpropylammonium trimethoxysilane, ethyldimethylbutylammonium chloride Trimethoxysilane, ethyl dimethyl butyl ammonium bromide trimethoxy silane, ethyl dimethyl butyl ammonium trimethoxy silane, ethyl dimethyl pentyl ammonium trimethoxy silane, ethyl dimethyl pentyl ammonium bromide trimethoxy silane, ethyl dimethyl pentyl ammonium trichloride Methoxysilane, ethyldimethylhexylammonium chloride trim Xylonsilane, ethyldimethylhexylammonium trimethoxysilane, ethyldimethylhexylammonium trimethoxysilane iodide, ethyldimethylheptylammonium trimethoxysilane chloride, ethyldimethylheptylammonium trimethoxysilane bromide, ethyldimethylheptylammonium trimethoxysilane iodide Ethyl dimethyl octyl ammonium trimethoxysilane, ethyl dimethyl octyl ammonium trimethoxy silane, ethyl dimethyl octyl ammonium trimethoxy silane iodide, diethyl methyl propyl ammonium trimethoxy silane chloride, diethyl methyl propyl ammonium trimethoxy silane, iodine Diethylmethylpropylammonium trimethoxysilane, dichloride chloride Tilmethylbutylammonium trimethoxysilane, diethylmethylbutylammonium trimethoxysilane bromide, diethylmethylbutylammonium trimethoxysilane iodide, diethylmethylpentylammonium trimethoxysilane chloride, diethylmethylpentylammonium trimethoxysilane bromide, diethyl iodide Methylpentylammonium trimethoxysilane, diethylmethylhexylammonium trimethoxysilane chloride, diethylmethylhexylammonium trimethoxysilane bromide, diethylmethylhexylammonium trimethoxysilane iodide, diethylmethylheptylammonium trimethoxysilane chloride, diethylmethylheptyl bromide Ammonium trimethoxysilane, diethylmethylheptylammonide iodide Mutrimethoxysilane, diethylmethyloctylammonium trimethoxysilane, diethylmethyloctylammonium trimethoxysilane bromide, diethylmethyloctylammonium trimethoxysilane iodide, tripropylmethylammonium trimethoxysilane chloride, tripropylmethylammonium trimethoxy bromide Silane, tripropylmethylammonium trimethoxysilane, tripropylethylammonium trimethoxysilane chloride, tripropylethylammonium trimethoxysilane bromide, tripropylethylammonium trimethoxysilane iodide, tripropylbutylammonium trimethoxysilane chloride, Tripropylbutylammonium trimethoxysilane, tripropylbutylammonium iodide Umtrimethoxysilane, tripropylpentylammonium chloride trimethoxysilane, tripropylpentylammonium bromide trimethoxysilane, tripropylpentylammonium iodide trimethoxysilane, tripropylhexylammonium chloride trimethoxysilane, tripropylhexylammonium trichloride Methoxysilane, tripropylhexylammonium iodide trimethoxysilane, tripropylheptylammonium trimethoxysilane chloride, tripropylheptylammonium trimethoxysilane bromide, tripropylheptylammonium iodide trimethoxysilane, tripropyloctylammonium trimethoxysilane chloride , Tripropyloctylammonium bromide trimethoxysilane, tripropyliodide iodide Cutylammonium trimethoxysilane, tributylmethylammonium trimethoxysilane, tributylmethylammonium trimethoxysilane, tributylmethylammonium trimethoxysilane iodide, tributylethylammonium trimethoxysilane, tributylethylammonium trimethoxysilane, iodine Tributylethylammonium trimethoxysilane, tributylpropylammonium trimethoxysilane chloride, tributylpropylammonium trimethoxysilane bromide, tributylpropylammonium trimethoxysilane iodide, tributylpentylammonium chloride trimethoxysilane, tributylpentylammonium trimethoxysilane bromide , Tributylpentylammonium iodide tri Toxisilane, tributylhexylammonium chloride trimethoxysilane, tributylhexylammonium bromide trimethoxysilane, tributylhexylammonium iodide trimethoxysilane, tributylheptylammonium chloride trimethoxysilane, tributylheptylammonium trimethoxysilane bromide, tributylheptylammonium iodide Trimethoxysilane, tributyloctylammonium chloride trimethoxysilane, tributyloctylammonium bromidetrimethoxysilane,
Tributyloctylammonium trimethoxysilane iodide, triphenylmethylammonium trimethoxysilane chloride, triphenylmethylammonium trimethoxysilane bromide, triphenylmethylammonium trimethoxysilane iodide, triphenylethylammonium trimethoxysilane chloride, tribromide tribromide Phenylethylammonium trimethoxysilane, triphenylethylammonium trimethoxysilane iodide, triphenylpropylammonium trimethoxysilane chloride, triphenylpropylammonium trimethoxysilane bromide, triphenylpropylammonium trimethoxysilane iodide, triphenylbutyl chloride Ammonium trimethoxysilane, triphenylbutylammonium bromide trimethoxysilane, iodine Triphenylbutylammonium trimethoxysilane, diphenyldimethylammonium trimethoxysilane, diphenyldimethylammonium trimethoxysilane, diphenyldimethylammonium trimethoxysilane iodide, diphenylmethylethylammonium trimethoxysilane, diphenylmethylethylammonium trichloride Methoxysilane, diphenylmethylethylammonium trimethoxysilane, diphenylmethylpropylammonium trimethoxysilane, diphenylmethylpropylammonium trimethoxysilane bromide, diphenylmethylpropylammonium trimethoxysilane iodide, diphenylmethylbutylammonium trimethoxysilane Diphenylmethylbutylammonium bromide Mutrimethoxysilane, diphenylmethylbutylammonium iodide trimethoxysilane, phenyltrimethylammonium trimethoxysilane chloride, phenyltrimethylammonium trimethoxysilane bromide, phenyltrimethylammonium trimethoxysilane iodide, phenyldimethylethylammonium trimethoxysilane, odor Phenyldimethylethylammonium trimethoxysilane, phenyldimethylethylammonium trimethoxysilane iodide, phenyldimethylpropylammonium trimethoxysilane chloride, phenyldimethylpropylammonium trimethoxysilane bromide, phenyldimethylpropylammonium trimethoxysilane iodide, phenyl chloride Dimethylbutylammonium trimethoxysilane, bromide Phenyldimethylbutylammonium trimethoxysilane, phenyldimethylbutylammonium trimethoxysilane iodide, diphenyldiethylammonium trimethoxysilane chloride, diphenyldiethylammonium trimethoxysilane bromide, diphenyldiethylammonium trimethoxysilane iodide, diphenylethylpropylammonium trichloride Methoxysilane, diphenylethylpropylammonium trimethoxysilane, diphenylethylpropylammonium trimethoxysilane iodide, diphenylethylbutylammonium trimethoxysilane, diphenylethylbutylammonium trimethoxysilane bromide, diphenylethylbutylammonium trimethoxy iodide Silane, phenyldiethylmethylan chloride Nitrotrimethoxysilane, phenyldiethylmethylammonium trimethoxysilane bromide, phenyldiethylmethylammonium trimethoxysilane iodide, phenyltriethylammonium trimethoxysilane chloride, phenyltriethylammonium bromide trimethoxysilane, phenyltriethylammonium trimethoxysilane iodide , Phenyldiethylpropylammonium trimethoxysilane bromide, phenyldiethylpropylammonium trimethoxysilane bromide, phenyldiethylpropylammonium trimethoxysilane iodide, phenyldiethylbutylammonium trimethoxysilane chloride, phenyldiethylbutylammonium trimethoxysilane bromide, iodine Phenyldiethylbutylammonium trimethoxysilane Trinaphthylmethylammonium trimethoxysilane chloride, trinaphthylmethylammonium trimethoxysilane bromide, trinaphthylmethylammonium trimethoxysilane iodide, trinaphthylethylammonium trimethoxysilane chloride, trinaphthylethylammonium trimethoxysilane bromide, iodide Trinaphthylethylammonium trimethoxysilane, trinaphthylpropylammonium trimethoxysilane chloride, trinaphthylpropylammonium trimethoxysilane bromide, trinaphthylpropylammonium trimethoxysilane iodide, trinaphthylbutylammonium trimethoxysilane chloride, trinaphthyl bromide Butylammonium trimethoxysilane, trinaphthylbutyl iodide trimethoxysilane, chloride Tribenzylmethylammonium trimethoxysilane, tribenzylmethylammonium trimethoxysilane bromide, tribenzylmethylammonium trimethoxysilane iodide, tribenzylethylammonium trimethoxysilane chloride, tribenzylethylammonium trimethoxysilane bromide, triiodide iodide Benzylethylammonium trimethoxysilane, tribenzylpropylammonium trimethoxysilane chloride, tribenzylpropylammonium trimethoxysilane bromide, tribenzylpropylammonium trimethoxysilane iodide, tribenzylbutylammonium trimethoxysilane chloride, tribenzylbutyl bromide Ammonium trimethoxysilane, tribenzylbutylammonium iodide trimethoxysilane, dichloride chloride Dildimethylammonium trimethoxysilane, dibenzyldimethylammonium trimethoxysilane bromide, dibenzyldimethylammonium trimethoxysilane iodide, dibenzylmethylethylammonium trimethoxysilane chloride, dibenzylmethylethylammonium trimethoxysilane bromide, iodide Dibenzylmethylethylammonium trimethoxysilane, dibenzylmethylpropylammonium trimethoxysilane, dibenzylmethylpropylammonium trimethoxysilane bromide, dibenzylmethylpropylammonium trimethoxysilane iodide, dibenzylmethylbutylammonium trimethoxysilane , Dibenzylmethylbutylammonium bromide trimethoxysilane, dibenzylmethylbutylammonium iodide Mutrimethoxysilane, benzyltrimethylammonium trimethoxysilane, benzyltrimethylammonium trimethoxysilane bromide, benzyltrimethylammonium trimethoxysilane iodide, benzyldimethylethylammonium trimethoxysilane chloride, benzyldimethylethylammonium trimethoxysilane bromide, iodine Benzyldimethylethylammonium trimethoxysilane, benzyldimethylpropylammonium trimethoxysilane, benzyldimethylpropylammonium trimethoxysilane bromide, benzyldimethylpropylammonium trimethoxysilane iodide, benzyldimethylbutylammonium trimethoxysilane, benzyl bromide Dimethylbutylammonium trimethoxysilane, iodide Benzyldimethylbutylammonium trimethoxysilane, dibenzyldiethylammonium trimethoxysilane chloride, dibenzyldiethylammonium trimethoxysilane bromide, dibenzyldiethylammonium trimethoxysilane iodide, dibenzylethylpropylammonium trimethoxysilane chloride, dibromide dibromide Benzylethylpropylammonium trimethoxysilane, dibenzylethylpropylammonium trimethoxysilane iodide,
Dibenzylethylbutylammonium trimethoxysilane chloride, dibenzylethylbutylammonium trimethoxysilane bromide, dibenzylethylbutylammonium trimethoxysilane iodide, benzyldiethylmethylammonium trimethoxysilane chloride, benzyldiethylmethylammonium trimethoxysilane bromide , Benzyldiethylmethylammonium trimethoxysilane iodide, benzyltriethylammonium trimethoxysilane chloride, benzyltriethylammonium trimethoxysilane bromide, benzyltriethylammonium trimethoxysilane iodide, benzyldiethylpropylammonium trimethoxysilane chloride, benzyldiethyl bromide Propylammonium trimethoxysilane, benzyldiethylpropyl iodide Ammonium trimethoxysilane, benzyldiethylbutylammonium trimethoxysilane, benzyldiethylbutylammonium trimethoxysilane, benzyldiethylbutylammonium trimethoxysilane iodide, triphenethylmethylammonium trimethoxysilane chloride, triphenethylmethylammonium trichloride Methoxysilane, triphenethylmethylammonium trimethoxysilane iodide, triphenethylethylammonium trimethoxysilane chloride, triphenethylethylammonium trimethoxysilane bromide, triphenethylethylammonium iodide trimethoxysilane, triphenethylpropylammonium trimethoxysilane chloride Triphenethylpropylammonium bromide trimethoxysilane, Triphenethylpropylammonium trimethoxysilane, triphenethylbutylammonium trimethoxysilane chloride, triphenethylbutylammonium trimethoxysilane bromide, triphenethylbutylammonium trimethoxysilane iodide, tetraphenylammonium trimethoxysilane chloride, tetraphenyl bromide Ammonium trimethoxysilane, tetraphenylammonium trimethoxysilane iodide, trimethylphenylammonium trimethoxysilane chloride, trimethylphenylammonium trimethoxysilane bromide, trimethylphenylammonium trimethoxysilane iodide, triethylphenylammonium trimethoxysilane chloride, bromide Triethylphenylammonium trimethoxysilane, triethyl iodide Phenylammonium trimethoxysilane, tripropylphenylammonium trimethoxysilane chloride, tripropylphenylammonium trimethoxysilane bromide, tripropylphenylammonium trimethoxysilane iodide, tributylphenylammonium trimethoxysilane chloride, tributylphenylammonium trimethoxy bromide Silane, tributylphenylammonium iodide trimethoxysilane, tetrabenzylammonium trimethoxysilane chloride, tetrabenzylammonium trimethoxysilane bromide, tetrabenzylammonium trimethoxysilane iodide, trimethylbenzylammonium trimethoxysilane chloride, trimethylbenzylammonium bromide Trimethoxysilane, trimethylbenzylammonium iodide Mutrimethoxysilane, triethylbenzylammonium trimethoxysilane, triethylbenzylammonium trimethoxysilane bromide, triethylbenzylammonium trimethoxysilane iodide, tripropylbenzylammonium trimethoxysilane chloride, tripropylbenzylammonium trimethoxysilane bromide, iodine Tripropylbenzylammonium trimethoxysilane, tributylbenzylammonium trimethoxysilane chloride, tributylbenzylammonium bromide trimethoxysilane, tributylbenzylammonium iodide trimethoxysilane, and the like. Without limitation, when Y in the general formula (3) is a field of an acyclic quaternary ammonio group represented by the general formula (11) No problem so long as it is. From the viewpoint of obtaining advantageous effects different from the effects of the present invention, such as the availability and synthesis of these silicon-containing compounds, Y in the general formula (3) is represented by the general formula ( Among the silicon-containing compounds in the case of the acyclic quaternary ammonio group represented by 11), tetramethylammonium trimethoxysilane chloride, tetramethylammonium trimethoxysilane bromide, tetramethylammonium trimethoxysilane iodide, tetraethyl chloride Ammonium trimethoxysilane, tetraethylammonium bromide trimethoxysilane, tetraethylammonium trimethoxysilane iodide, trimethylethylammonium trimethoxysilane chloride, trimethylethylammonium trimethoxysilane bromide, trimethylethylammonium iodide trimethylsilane Xylsilane, trimethylpropylammonium trimethoxysilane, trimethylpropylammonium trimethoxysilane bromide, trimethylpropylammonium trimethoxysilane iodide, trimethylbutylammonium trimethoxysilane chloride, trimethylbutylammonium bromide trimethoxysilane, trimethylbutylammonium iodide Trimethoxysilane, triethylmethylammonium chloride trimethoxysilane, triethylmethylammonium trimethoxysilane bromide, triethylmethylammonium trimethoxysilane iodide, triethylpropylammonium trimethoxysilane chloride, triethylpropylammonium trimethoxysilane bromide, triethyl iodide Propyl ammonium trimethoxysilane, trichloride Tilbutylammonium trimethoxysilane, triethylbutylammonium bromide trimethoxysilane, triethylbutylammonium iodide trimethoxysilane, diethyldimethylammonium trimethoxysilane chloride, diethyldimethylammonium trimethoxysilane, diethyldimethylammonium trimethoxysilane iodide , Ethyldimethylpropylammonium trimethoxysilane, ethyldimethylpropylammonium trimethoxysilane bromide, ethyldimethylpropylammonium trimethoxysilane iodide, ethyldimethylbutylammonium trimethoxysilane chloride, ethyldimethylbutylammonium trimethoxysilane, iodine Ethyldimethylbutylammonium trimethoxysilane, diethyl chloride Tylpropylammonium trimethoxysilane, diethylmethylpropylammonium trimethoxysilane bromide, diethylmethylpropylammonium trimethoxysilane iodide, diethylmethylbutylammonium trimethoxysilane chloride, diethylmethylbutylammonium trimethoxysilane bromide, diethylmethyl iodide Butyl ammonium trimethoxysilane and the like are preferable. In addition, alkyl groups such as propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group and the like exemplified here are not limited to linear n-forms, but are isoforms, sec-forms, tert-forms. It may be branched or cyclic like a body.

Furthermore, specific examples of the silicon-containing compound in the case where Y in the general formula (3) is a heterocyclic non-aromatic quaternary ammonio group represented by the general formula (12) include, for example, fluorinated N-methyl-1 -Pyrrolidinium methyltrimethoxysilane, N-methyl-1-pyrrolidinium methyltrimethoxysilane chloride, N-methyl-1-pyrrolidinium methyltrimethoxysilane bromide, N-methyl-1-pyrrolidiiodide N-methyltrimethoxysilane, N-methyl-1-pyrrolidinium methyltriethoxysilane fluoride, N-methyl-1-pyrrolidinium methyltriethoxysilane chloride, N-methyl-1-pyrrolidinium methyltribromide Ethoxysilane, N-methyl-1-pyrrolidinium iodide methyltriethoxysilane, N-methyl-1-pyrrolidinium fluoride Rutripropoxysilane, N-methyl-1-pyrrolidinium methyltripropoxysilane chloride, N-methyl-1-pyrrolidinium methyltripropoxysilane bromide, N-methyl-1-pyrrolidinium methyltripropoxysilane iodide N-methyl-1-pyrrolidinium methyltrichlorosilane fluoride, N-methyl-1-pyrrolidinium methyltrichlorosilane chloride, N-methyl-1-pyrrolidinium methyltrichlorosilane bromide, N-methyl iodide -1-pyrrolidinium methyltrichlorosilane, N-methyl-1-pyrrolidinium methyltribromosilane fluoride, N-methyl-1-pyrrolidinium methyltribromosilane chloride, N-methyl-1-pyrrole bromide Dinium methyltribromosilane, N-methyl-1-pyrrolidinium methyl iodide Tribromosilane, N-methyl-1-pyrrolidinium methyltriiodosilane fluoride, N-methyl-1-pyrrolidinium methyltriiodosilane chloride, N-methyl-1-pyrrolidinium methyltriiodosilane bromide N-methyl-1-pyrrolidinium methyltriiodosilane iodide, N-methyl-1-pyrrolidinium ethyltrimethoxysilane chloride, N-methyl-1-pyrrolidinium ethyltrimethoxysilane bromide, iodide N-methyl-1-pyrrolidinium ethyltrimethoxysilane, N-methyl-1-pyrrolidinium propyltrimethoxysilane chloride, N-methyl-1-pyrrolidinium propyltrimethoxysilane bromide, N-methyl iodide -1-pyrrolidinium propyltrimethoxysilane, N-methyl-1-pyrrolidinium butyl chloride Limethoxysilane, N-methyl-1-pyrrolidinium butyltrimethoxysilane bromide, N-methyl-1-pyrrolidinium butyltrimethoxysilane iodide, N-methyl-1-pyrrolidinium pentyltrimethoxysilane chloride N-methyl-1-pyrrolidinium pentyltrimethoxysilane bromide, N-methyl-1-pyrrolidinium pentyltrimethoxysilane iodide, N-methyl-1-pyrrolidinium hexyltrimethoxysilane chloride, bromide N-methyl-1-pyrrolidinium hexyltrimethoxysilane, N-methyl-1-pyrrolidinium hexyltrimethoxysilane iodide, N-methyl-1-pyrrolidinium heptyltrimethoxysilane chloride, N-methyl bromide -1-pyrrolidinium heptyltrimethoxysilane, N-methyl-1-pyroiodide Dinium heptyltrimethoxysilane, N-methyl-1-pyrrolidinium octyltrimethoxysilane chloride, N-methyl-1-pyrrolidinium octyltrimethoxysilane bromide, N-methyl-1-pyrrolidinium octyl iodide Trimethoxysilane, N-ethyl-1-pyrrolidinium methyltrimethoxysilane chloride, N-ethyl-1-pyrrolidinium methyltrimethoxysilane bromide, N-ethyl-1-pyrrolidinium methyltrimethoxysilane iodide N-ethyl-1-pyrrolidinium ethyltrimethoxysilane chloride, N-ethyl-1-pyrrolidinium ethyltrimethoxysilane bromide, N-ethyl-1-pyrrolidinium ethyltrimethoxysilane iodide, N chloride -Ethyl-1-pyrrolidinium propyltrimethoxysilane, N-ethyl bromide 1-pyrrolidinium propyltrimethoxysilane, N-ethyl-1-pyrrolidinium propyltrimethoxysilane iodide, N-ethyl-1-pyrrolidinium butyltrimethoxysilane chloride, N-ethyl-1-pyrrole bromide Dinium butyltrimethoxysilane, N-ethyl-1-pyrrolidinium butyltrimethoxysilane iodide, N-propyl-1-pyrrolidinium methyltrimethoxysilane chloride, N-propyl-1-pyrrolidinium methyl bromide Trimethoxysilane, N-propyl-1-pyrrolidinium methyltrimethoxysilane iodide, N-propyl-1-pyrrolidinium ethyltrimethoxysilane chloride, N-propyl-1-pyrrolidinium ethyltrimethoxysilane bromide N-propyl-1-pyrrolidinium ethyltrimethoxysilane iodide N-propyl-1-pyrrolidinium propyltrimethoxysilane chloride, N-propyl-1-pyrrolidinium propyltrimethoxysilane bromide, N-propyl-1-pyrrolidinium propyltrimethoxysilane iodide, N chloride -Propyl-1-pyrrolidinium butyltrimethoxysilane, N-propyl-1-pyrrolidinium butyltrimethoxysilane bromide, N-propyl-1-pyrrolidinium butyltrimethoxysilane iodide, N-butyl chloride 1-pyrrolidinium methyltrimethoxysilane, N-butyl-1-pyrrolidinium methyltrimethoxysilane bromide, N-butyl-1-pyrrolidinium methyltrimethoxysilane iodide, N-butyl-1-pyrrole chloride Dinium ethyl trimethoxysilane, N-butyl-1-pyrrolidinium ethyl bromide Limethoxysilane, N-butyl-1-pyrrolidinium ethyltrimethoxysilane iodide, N-butyl-1-pyrrolidiniumpropyltrimethoxysilane chloride, N-butyl-1-pyrrolidiniumpropyltrimethoxysilane bromide N-butyl-1-pyrrolidinium propyltrimethoxysilane iodide, N-butyl-1-pyrrolidinium butyltrimethoxysilane chloride, N-butyl-1-pyrrolidinium butyltrimethoxysilane bromide, iodide N-butyl-1-pyrrolidinium butyltrimethoxysilane, N-pentyl-1-pyrrolidinium methyltrimethoxysilane, N-pentyl-1-pyrrolidinium methyltrimethoxysilane bromide, N-pentyl iodide -1-pyrrolidinium methyltrimethoxysilane, N-pentyl-1-pyrochloride Dinium ethyltrimethoxysilane, N-pentyl-1-pyrrolidinium ethyltrimethoxysilane bromide, N-pentyl-1-pyrrolidinium ethyltrimethoxysilane iodide, N-pentyl-1-pyrrolidinium propyl chloride Trimethoxysilane, N-pentyl-1-pyrrolidinium propyltrimethoxysilane bromide, N-pentyl-1-pyrrolidinium propyltrimethoxysilane iodide, N-pentyl-1-pyrrolidinium butyltrimethoxysilane chloride N-pentyl-1-pyrrolidinium butyltrimethoxysilane bromide, N-pentyl-1-pyrrolidinium butyltrimethoxysilane iodide, N-hexyl-1-pyrrolidinium methyltrimethoxysilane chloride, bromide N-hexyl-1-pyrrolidinium methyltrimethoxysilane, N-hexyl iodide-1-pyrrolidinium methyltrimethoxysilane, N-hexyl-1-pyrrolidinium ethyltrimethoxysilane chloride, N-hexyl-1-pyrrolidinium ethyltrimethoxysilane bromide, N iodide -Hexyl-1-pyrrolidinium ethyltrimethoxysilane, N-hexyl-1-pyrrolidiniumpropyltrimethoxysilane chloride, N-hexyl-1-pyrrolidiniumpropyltrimethoxysilane bromide, N-hexyl iodide- 1-pyrrolidinium propyltrimethoxysilane, N-hexyl-1-pyrrolidinium butyltrimethoxysilane chloride, N-hexyl-1-pyrrolidinium butyltrimethoxysilane bromide, N-hexyl-1-pyrrole iodide Dinium butyltrimethoxysilane, N-heptyl-1-pyrrolidinyl chloride Mumethyltrimethoxysilane, N-heptyl-1-pyrrolidinium bromide methyltrimethoxysilane, N-heptyl-1-pyrrolidinium methyltrimethoxysilane iodide, N-heptyl-1-pyrrolidinium ethyltrichloride Methoxysilane, N-heptyl-1-pyrrolidinium ethyltrimethoxysilane bromide, N-heptyl-1-pyrrolidinium ethyltrimethoxysilane iodide, N-heptyl-1-pyrrolidiniumpropyltrimethoxysilane chloride, N-heptyl-1-pyrrolidinium propyltrimethoxysilane bromide, N-heptyl-1-pyrrolidinium propyltrimethoxysilane iodide, N-heptyl-1-pyrrolidinium butyltrimethoxysilane chloride, N-bromide -Heptyl-1-pyrrolidinium butyltrimethoxysilane, iodine N-heptyl-1-pyrrolidinium butyltrimethoxysilane, N-octyl-1-pyrrolidinium methyltrimethoxysilane, N-octyl-1-pyrrolidinium methyltrimethoxysilane bromide, N-octyl iodide -1-pyrrolidinium methyltrimethoxysilane, N-octyl-1-pyrrolidinium ethyltrimethoxysilane, N-octyl-1-pyrrolidinium ethyltrimethoxysilane bromide, N-octyl-1-iodide Pyrrolidinium ethyltrimethoxysilane, N-octyl-1-pyrrolidinium propyltrimethoxysilane chloride, N-octyl-1-pyrrolidinium propyltrimethoxysilane bromide, N-octyl-1-pyrrolidinium iodide Propyltrimethoxysilane, N-octyl-1-pyrrolidinium chloride Tiltrimethoxysilane, N-octyl-1-pyrrolidinium butyltrimethoxysilane bromide, N-octyl-1-pyrrolidinium butyltrimethoxysilane iodide, N-methyl-1-piperidinium methyltrimethoxy chloride Silane, N-methyl-1-piperidinium methyltrimethoxysilane bromide, N-methyl-1-piperidinium methyltrimethoxysilane iodide, N-methyl-1-piperidinium ethyltrimethoxysilane chloride, odor N-methyl-1-piperidinium ethyltrimethoxysilane, N-methyl-1-piperidinium ethyltrimethoxysilane iodide, N-methyl-1-piperidiniumpropyltrimethoxysilane chloride, N-bromide Methyl-1-piperidiniumpropyltrimethoxysilane,
N-methyl-1-piperidinium propyltrimethoxysilane iodide, N-methyl-1-piperidinium butyltrimethoxysilane chloride, N-methyl-1-piperidinium butyltrimethoxysilane bromide, N iodide -Methyl-1-piperidinium butyltrimethoxysilane, N-ethyl-1-piperidinium methyltrimethoxysilane chloride, N-ethyl-1-piperidinium methyltrimethoxysilane bromide, N-ethyl iodide- 1-piperidinium methyltrimethoxysilane, N-ethyl-1-piperidinium ethyltrimethoxysilane chloride, N-ethyl-1-piperidinium ethyltrimethoxysilane bromide, N-ethyl-1-pidium iodide Peridinium ethyltrimethoxysilane, N-ethyl-1-piperidiniumpropyltrimethoxysilane chloride N-ethyl-1-piperidinium propyltrimethoxysilane bromide, N-ethyl-1-piperidinium propyltrimethoxysilane iodide, N-ethyl-1-piperidinium butyltrimethoxysilane chloride, odor N-ethyl-1-piperidinium butyltrimethoxysilane, N-ethyl-1-piperidinium butyltrimethoxysilane iodide, N-methyl-1-pyrroliummethyltrimethoxysilane chloride, N-methyl bromide -1-pyrroliummethyltrimethoxysilane, N-methyl-1-pyrroliummethyltrimethoxysilane iodide, N-methyl-1-pyrroliumethyltrimethoxysilane chloride, N-methyl-1-pyrroliumethyl bromide Trimethoxysilane, N-methyl-1-pyrrolium iodide trimethoxysilane, N-methyl-1-pyrroliumpropyltrimethoxysilane, N-methyl-1-pyrroliumpropyltrimethoxysilane bromide, N-methyl-1-pyrroliumpropyltrimethoxysilane iodide, N-methyl-1 chloride -Pyrrolonium butyltrimethoxysilane, N-methyl-1-pyrrolium butyltrimethoxysilane bromide, N-methyl-1-pyrrolium butyltrimethoxysilane iodide, N-ethyl-1-pyrrolium methyltrimethoxy chloride Silane, N-ethyl-1-pyrrolium methyltrimethoxysilane bromide, N-ethyl-1-pyrrolium methyltrimethoxysilane iodide, N-ethyl-1-pyrrolium ethyltrimethoxysilane chloride, N-bromide Ethyl-1-pyrrolium ethyltrimethoxysilane, N-ethyl iodide 1-pyrroliniumethyltrimethoxysilane, N-ethyl-1-pyrroliumpropyltrimethoxysilane chloride, N-ethyl-1-pyrroliumpropyltrimethoxysilane bromide, N-ethyl-1-pyrroliumpropyltriiodide Methoxysilane, N-ethyl-1-pyrroliumbutyltrimethoxysilane chloride, N-ethyl-1-pyrroliumbutyltrimethoxysilane bromide, N-ethyl-1-pyrroliumbutyltrimethoxysilane iodide, N-chloride Methyl-2,3-dihydro-1H-1-pyrroliummethyltrimethoxysilane, N-methyl-2,3-dihydro-1H-1-pyrroliummethyltrimethoxysilane bromide, N-methyl-2 iodide, 3-dihydro-1H-1-pyrroliniummethyltrimethoxysilane, N-methyl-2 chloride 5-dihydro-1H-1-pyrroliniummethyltrimethoxysilane, N-methyl-2,5-dihydro-1H-1-pyrroliummethyltrimethoxysilane bromide, N-methyl-2,5-dihydro-iodide 1H-1-pyrroliniummethyltrimethoxysilane, N-methyl-1,2,3,4-tetrahydro-1-pyridiniummethyltrimethoxysilane chloride, N-methyl-1,2,3,4-tetrahydro-bromide 1-pyridinium methyltrimethoxysilane, N-methyl-1,2,3,4-tetrahydro-1-pyridiniummethyltrimethoxysilane iodide, N-methyl-1,2,5,6-tetrahydro-1-pyridinium chloride Methyltrimethoxysilane, N-methyl-1,2,5,6-tetrahydro-1-pyridinium methyltrimethoxysilane bromide N-methyl-1,2,5,6-tetrahydro-1-pyridinium methyltrimethoxysilane, N-methyl-1,2-dihydro-1-pyridiniummethyltrimethoxysilane chloride, N-methyl bromide -1,2-dihydro-1-pyridinium methyltrimethoxysilane, iodide N-methyl-1,2-dihydro-1-pyridiniummethyltrimethoxysilane, N-methyl-1H, 3H-1-pyridiniummethyltrimethoxy chloride Silane, N-methyl-1H, 3H-1-pyridiniummethyltrimethoxysilane bromide, N-methyl-1H, 3H-1-pyridiniummethyltrimethoxysilane iodide, N-methyl-1-pyrrolidinium phenyltrichloride Methoxysilane, N-methyl-1-pyrrolidinium bromide phenyltrimethoxysilane, iodide N-methyl-1-pyrrolidinium phenyltrimethoxysilane, N-ethyl-1-pyrrolidinium phenyltrimethoxysilane, N-ethyl-1-pyrrolidinium phenyltrimethoxysilane bromide, N-ethyl iodide -1-pyrrolidinium phenyltrimethoxysilane, N-propyl-1-pyrrolidinium phenyltrimethoxysilane, N-propyl-1-pyrrolidinium phenyltrimethoxysilane bromide, N-propyl-1-iodide Pyrrolidinium phenyltrimethoxysilane, N-butyl-1-pyrrolidinium chloride trimethoxysilane, N-butyl-1-pyrrolidinium phenyltrimethoxysilane bromide, N-butyl-1-pyrrolidinium iodide Phenyltrimethoxysilane, N-pentyl-1-pyrrolidinium chloride Nyltrimethoxysilane, N-pentyl-1-pyrrolidinium phenyltrimethoxysilane bromide, N-pentyl-1-pyrrolidinium phenyltrimethoxysilane iodide, N-hexyl-1-pyrrolidinium phenyltrimethoxy chloride Silane, N-hexyl bromide-1-pyrrolidinium phenyltrimethoxysilane, N-hexyl-1-pyrrolidinium phenyltrimethoxysilane iodide, N-heptyl-1-pyrrolidinium phenyltrimethoxysilane chloride, odor N-heptyl-1-pyrrolidinium phenyltrimethoxysilane, N-heptyl-1-pyrrolidinium phenyltrimethoxysilane iodide, N-octyl-1-pyrrolidinium phenyltrimethoxysilane chloride, N-bromide Octyl-1-pyrrolidinium phenyltrimethoxy N-octyl-1-pyrrolidinium phenyltrimethoxysilane, N-methyl-1-piperidinium phenyltrimethoxysilane chloride, N-methyl-1-piperidinium phenyltrimethoxysilane bromide, iodine N-methyl-1-piperidinium phenyltrimethoxysilane, N-ethyl-1-piperidinium phenyltrimethoxysilane chloride, N-ethyl-1-piperidinium phenyltrimethoxysilane bromide, N-iodide Ethyl-1-piperidinium phenyltrimethoxysilane, N-methyl-1-pyrrolium phenyltrimethoxysilane chloride, N-methyl-1-pyrrolium phenyltrimethoxysilane bromide, N-methyl-1-pyrrole iodide Nitrophenyltrimethoxysilane, N-ethyl-1-pyrrolinium chloride Rutrimethoxysilane, N-ethyl-1-pyrrolinium phenyltrimethoxysilane bromide, N-ethyl-1-pyrrolinium phenyltrimethoxysilane iodide, N-methyl-2,3-dihydro-1H-1-pyrrole chloride Nitrophenyltrimethoxysilane, N-methyl-2,3-dihydro-1H-1-pyrrolinium bromide trimethoxysilane, N-methyl-2,3-dihydro-1H-1-pyrrolinium phenyltrimethoxy iodide Silane, N-methyl-2,5-dihydro-1H-1-pyrroliumphenyltrimethoxysilane chloride, N-methyl-2,5-dihydro-1H-1-pyrroliumphenyltrimethoxysilane bromide, N-iodide -Methyl-2,5-dihydro-1H-1-pyrrolium phenyltrimethoxysilane, N-methyl chloride 1,2,3,4-tetrahydro-1-pyridinium phenyltrimethoxysilane, N-methyl-1,2,3,4-tetrahydro-1-pyridiniumphenyltrimethoxysilane bromide, N-methyl-1, iodide 2,3,4-tetrahydro-1-pyridinium phenyltrimethoxysilane, N-methyl-1,2,5,6-tetrahydro-1-pyridinium phenyltrimethoxysilane, N-methyl-1,2,5 bromide , 6-Tetrahydro-1-pyridiniumphenyltrimethoxysilane, N-methyl-1,2,5,6-tetrahydro-1-pyridiniumphenyltrimethoxysilane iodide, N-methyl-1,2-dihydro-1-chloride Pyridinium phenyltrimethoxysilane, N-methyl-1,2-dihydro-1-pyridinium phenyl bromide Limethoxysilane, iodinated N-methyl-1,2-dihydro-1-pyridiniumphenyltrimethoxysilane, N-methyl-1H, 3H-1-pyridiniumphenyltrimethoxysilane chloride, N-methyl-1H, 3H bromide -1-pyridinium phenyltrimethoxysilane, iodide N-methyl-1H, 3H-1-pyridiniumphenyltrimethoxysilane, N-methyl-1-pyrrolidinium benzyltrimethoxysilane chloride, N-methyl-1-bromide Pyrrolidinium benzyltrimethoxysilane, N-methyl-1-pyrrolidinium benzyltrimethoxysilane iodide, N-ethyl-1-pyrrolidinium benzyltrimethoxysilane chloride, N-ethyl-1-pyrrolidinium bromide Benzyltrimethoxysilane, N-ethyl-1-pyrrolidinium iodide N-propyl-1-pyrrolidinium benzyltrimethoxysilane, N-propyl-1-pyrrolidinium benzyltrimethoxysilane bromide, N-propyl-1-pyrrolidinium benzyltriiodide Methoxysilane, N-butyl-1-pyrrolidinium benzyltrimethoxysilane chloride, N-butyl-1-pyrrolidinium benzyltrimethoxysilane bromide, N-butyl-1-pyrrolidinium benzyltrimethoxysilane iodide, N-pentyl-1-pyrrolidinium benzyltrimethoxysilane chloride, N-pentyl-1-pyrrolidinium benzyltrimethoxysilane bromide, N-pentyl-1-pyrrolidinium benzyltrimethoxysilane iodide, N-chloride Hexyl-1-pyrrolidinium benzyltrimethoxysilane, N-hexyl-1-pyrrolidinium benzyltrimethoxysilane, N-hexyl-1-pyrrolidinium benzyltrimethoxysilane iodide, N-heptyl-1-pyrrolidinium benzyltrimethoxysilane chloride, N-bromide Heptyl-1-pyrrolidinium benzyltrimethoxysilane, N-heptyl-1-pyrrolidinium benzyltrimethoxysilane iodide, N-octyl-1-pyrrolidinium benzyltrimethoxysilane chloride, N-octyl-1 bromide -Pyrrolidinium benzyltrimethoxysilane, N-octyl-1-pyrrolidinium benzyltrimethoxysilane iodide, N-methyl-1-piperidinium benzyltrimethoxysilane chloride, N-methyl-1-piperidibromide Ni-benzyltrimethoxysilane, N-methyl-1-pi iodide Lizinium benzyltrimethoxysilane, N-ethyl-1-piperidinium benzyltrimethoxysilane chloride, N-ethyl-1-piperidinium benzyltrimethoxysilane bromide, N-ethyl-1-piperidinium benzyl iodide Trimethoxysilane, N-methyl-1-pyrroliumbenzyltrimethoxysilane chloride, N-methyl-1-pyrroliumbenzyltrimethoxysilane bromide,
N-methyl-1-pyrrolium benzyltrimethoxysilane iodide, N-ethyl-1-pyrrolium benzyltrimethoxysilane chloride, N-ethyl-1-pyrrolium benzyltrimethoxysilane bromide, N-ethyl iodide 1-pyrroliumbenzyltrimethoxysilane, N-methyl-2,3-dihydro-1H-1-pyrroliumbenzyltrimethoxysilane chloride, N-methyl-2,3-dihydro-1H-1-pyrrolinium benzyl bromide Trimethoxysilane, N-methyl-2,3-dihydro-1H-1-pyrroliumbenzyltrimethoxysilane iodide, N-methyl-2,5-dihydro-1H-1-pyrroliumbenzyltrimethoxysilane chloride, odor N-methyl-2,5-dihydro-1H-1-pyrroliumbenzyltrimethoxysilane, N-methyl-2,5-dihydro-1H-1-pyrrolium benzyltrimethoxysilane uride, N-methyl-1,2,3,4-tetrahydro-1-pyridinium benzyltrimethoxysilane chloride, N-bromide Methyl-1,2,3,4-tetrahydro-1-pyridinium benzyltrimethoxysilane, N-methyl-1,2,3,4-tetrahydro-1-pyridiniumbenzyltrimethoxysilane iodide, N-methyl-1 chloride , 2,5,6-tetrahydro-1-pyridinium benzyltrimethoxysilane, N-methyl-1,2,5,6-tetrahydro-1-pyridinium benzyltrimethoxysilane, N-methyl-1,2 iodide , 5,6-tetrahydro-1-pyridinium benzyltrimethoxysilane, N-methyl-1,2-dihydro-1 chloride Pyridinium benzyltrimethoxysilane, N-methyl-1,2-dihydro-1-pyridiniumbenzyltrimethoxysilane bromide, N-methyl-1,2-dihydro-1-pyridiniumbenzyltrimethoxysilane iodide, N-methyl chloride -1H, 3H-1-pyridinium benzyltrimethoxysilane, N-methyl-1H, 3H-1-pyridinium benzyltrimethoxysilane bromide, N-methyl-1H, 3H-1-pyridinium benzyltrimethoxysilane iodide, etc. Although not necessarily limited to the silicon-containing compounds exemplified here, Y in the general formula (3) is a heterocyclic non-aromatic quaternary ammonio group represented by the general formula (12). There is no problem if there is. The alkyl groups such as propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group and the like exemplified here are not limited to linear n-forms, but are isoforms, sec-forms, tert-forms. It may be branched or cyclic like a body.

  Specific examples of the silicon-containing compound in the case where Y in the general formula (3) is a heterocyclic aromatic quaternary ammonio group represented by the general formula (13) include, for example, 1-pyridinium methyltrimethoxysilane fluoride. 1-pyridinium methyltrimethoxysilane chloride, 1-pyridinium methyltrimethoxysilane bromide, 1-pyridinium methyltrimethoxysilane iodide, 1-pyridinium methyltriethoxysilane fluoride, 1-pyridiniummethyltriethoxysilane chloride, odor 1-pyridinium methyltriethoxysilane, 1-pyridiniummethyltriethoxysilane iodide, 1-pyridiniummethyltripropoxysilane fluoride, 1-pyridiniummethyltripropoxysilane chloride, 1-pyridiniummethyltripropoxysilane bromide, iodide 1-pi Diniummethyltripropoxysilane, 1-pyridiniummethyltrichlorosilane fluoride, 1-pyridiniummethyltrichlorosilane chloride, 1-pyridiniummethyltrichlorosilane bromide, 1-pyridiniummethyltrichlorosilane iodide, 1-pyridiniummethyltribromofluoride Silane, 1-pyridinium methyltribromosilane chloride, 1-pyridinium methyltribromosilane bromide, 1-pyridinium methyltribromosilane iodide, 1-pyridinium methyltriiodosilane fluoride, 1-pyridiniummethyltriiodosilane chloride, 1-pyridinium methyltriiodosilane bromide, 1-pyridinium methyltriiodosilane iodide, 1-pyridinium ethyltrimethoxysilane chloride, 1-pyridiniumethyltrimethoxysilane bromide 1-pyridinium ethyltrimethoxysilane iodide, 1-pyridiniumpropyltrimethoxysilane chloride, 1-pyridiniumpropyltrimethoxysilane bromide, 1-pyridiniumpropyltrimethoxysilane iodide, 1-pyridiniumbutyltrimethoxysilane chloride, odor 1-pyridinium butyltrimethoxysilane, 1-pyridiniumbutyltrimethoxysilane iodide, 1-pyridiniumpentyltrimethoxysilane chloride, 1-pyridiniumpentyltrimethoxysilane bromide, 1-pyridiniumpentyltrimethoxysilane iodide, 1 chloride -Pyridinium hexyltrimethoxysilane, 1-pyridinium hexyltrimethoxysilane bromide, 1-pyridinium hexyltrimethoxysilane iodide, 1-pyridinium heptyltrimethoxy chloride Sisilane, 1-pyridinium heptyltrimethoxysilane bromide, 1-pyridinium heptyltrimethoxysilane iodide, 1-pyridinium octyltrimethoxysilane chloride, 1-pyridinium octyltrimethoxysilane bromide, 1-pyridinium octyltrimethoxysilane iodide 1-quinolinium methyltrimethoxysilane chloride, 1-quinolinium methyltrimethoxysilane bromide, 1-quinolinium methyltrimethoxysilane iodide, 1-quinolinium ethyltrimethoxysilane chloride, 1 bromide -Quinolinium ethyltrimethoxysilane, 1-quinolinium ethyltrimethoxysilane iodide, 1-quinoliniumpropyltrimethoxysilane chloride, 1-quinoliniumpropyltrimethoxysilane bromide, 1-quinolinyl iodide Nitropropyltrime 1-quinolinium butyltrimethoxysilane chloride, 1-quinolinium butyltrimethoxysilane bromide, 1-quinolinium butyltrimethoxysilane iodide, 1-quinolinium pentyltrimethoxysilane chloride, bromide 1-quinolinium pentyltrimethoxysilane, 1-quinolinium pentyltrimethoxysilane iodide, 1-quinolinium hexyltrimethoxysilane chloride, 1-quinolinium hexyltrimethoxysilane bromide, 1-quinone iodide Norinium hexyltrimethoxysilane, 1-quinolinium heptyltrimethoxysilane chloride, 1-quinolinium heptyltrimethoxysilane bromide, 1-quinolinium heptyltrimethoxysilane iodide, 1-quinolinium octyltrichloride Methoxysilane, 1-quinolinium octyl bromide Trimethoxysilane, 1-quinolinium octyltrimethoxysilane iodide, 2-isoquinolinium methyltrimethoxysilane chloride, 2-isoquinolinium methyltrimethoxysilane bromide, 2-isoquinolinium methyl iodide Trimethoxysilane, 2-isoquinolinium ethyltrimethoxysilane chloride, 2-isoquinolinium ethyltrimethoxysilane bromide, 2-isoquinolinium ethyltrimethoxysilane iodide, 2-isoquinoliniumpropyl chloride Trimethoxysilane, 2-isoquinoliniumpropyltrimethoxysilane bromide, 2-isoquinoliniumpropyltrimethoxysilane iodide, 2-isoquinoliniumbutyltrimethoxysilane chloride, 2-isoquinolinium bromide Butyltrimethoxysilane, 2-isoquinolinium butyl iodide Limethoxysilane, 2-isoquinolinium chloride tiltrimethoxysilane, 2-isoquinolinium pentyltrimethoxysilane bromide, 2-isoquinolinium pentyltrimethoxysilane iodide, 2-isoquinolinium hexyl chloride Trimethoxysilane, 2-isoquinolinium hexyltrimethoxysilane bromide, 2-isoquinolinium hexyltrimethoxysilane iodide, 2-isoquinolinium heptyltrimethoxysilane chloride, 2-isoquinolinium bromide Heptyltrimethoxysilane, 2-isoquinolinium iodide heptyltrimethoxysilane, 2-isoquinolinium octyltrimethoxysilane chloride, 2-isoquinolinium octyltrimethoxysilane bromide, 2-isoquinolyl iodide Nitrooctyltrimethoxysilane, 1-pyridinyl chloride Mphenyltrimethoxysilane, 1-pyridinium phenyltrimethoxysilane bromide, 1-pyridinium phenyltrimethoxysilane iodide, 1-quinolinium phenyltrimethoxysilane chloride, 1-quinolinium phenyltrimethoxysilane bromide, iodine 1-quinolinium phenyltrimethoxysilane, 2-isoquinolinium phenyltrimethoxysilane chloride, 2-isoquinolinium phenyltrimethoxysilane bromide, 2-isoquinolinium phenyltrimethoxysilane iodide, chloride 1-pyridinium benzyltrimethoxysilane, 1-pyridinium benzyltrimethoxysilane bromide, 1-pyridinium benzyltrimethoxysilane iodide, 1-quinolinium benzyltrimethoxysilane chloride, 1-quinolinium benzyltrimethoxy bromide Silane, 1-quinolinium benzyltrimethoxysilane iodide, 2-isoquinolinium benzyltrimethoxysilane chloride, 2-isoquinolinium benzyltrimethoxysilane bromide, 2-isoquinolinium benzyltrimethoxy iodide Although silane etc. are mentioned, it is not necessarily limited to the silicon-containing compound illustrated here, Y in General formula (3) is a heterocyclic aromatic quaternary ammonio group shown by General formula (13). Anything is acceptable. The alkyl groups such as propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group and the like exemplified here are not limited to linear n-forms, but are isoforms, sec-forms, tert-forms. It may be branched or cyclic like a body.

Furthermore, specific examples of the silicon-containing compound when Y in the general formula (3) is a group derived from a heterocyclic non-aromatic quaternary ammonium ion represented by the general formula (14) include, for example, fluoride N, N-dimethyl-2-pyrrolidinium trimethoxysilane, N, N-dimethyl-2-pyrrolidinium trimethoxysilane chloride, N, N-dimethyl-2-pyrrolidinium trimethoxysilane bromide, N-iodide, N-dimethyl-2-pyrrolidinium trimethoxysilane, fluorinated N, N-dimethyl-2-pyrrolidinium triethoxysilane, N, N-dimethyl-2-pyrrolidinium triethoxysilane chloride, N, bromide N-dimethyl-2-pyrrolidinium triethoxysilane, iodide N, N-dimethyl-2-pyrrolidinium triethoxysilane, fluoride N, N-dimethyl- -Pyrrolidinium tripropoxysilane, N, N-dimethyl-2-pyrrolidinium tripropoxysilane chloride, N, N-dimethyl-2-pyrrolidinium tripropoxysilane bromide, N, N-dimethyl-2 iodide -Pyrrolidinium tripropoxysilane, N, N-dimethyl-2-pyrrolidinium trichlorosilane fluoride, N, N-dimethyl-2-pyrrolidinium trichlorosilane chloride, N, N-dimethyl-2-pyrrole bromide Dinium trichlorosilane, N, N-dimethyl-2-pyrrolidinium iodide trichlorosilane, N, N-dimethyl-2-pyrrolidinium fluoride tribromosilane, N, N-dimethyl-2-pyrrolidinium chloride Tribromosilane, N, N-dimethyl-2-pyrrolidinium bromide tribromosilane, N, N-dimethyl-2 iodide Pyrrolidinium tribromosilane, fluorinated N, N-dimethyl-2-pyrrolidinium triiodosilane, N, N-dimethyl-2-pyrrolidinium triiodosilane chloride, N, N-dimethyl-2-bromide Pyrrolidinium triiodosilane, N, N-dimethyl-2-pyrrolidinium triiodosilane iodide, N, N-dimethyl-2-pyrrolidinium methyltrimethoxysilane chloride, N, N-dimethyl-2 bromide -Pyrrolidinium methyltrimethoxysilane, N, N-dimethyl-2-pyrrolidinium methyltrimethoxysilane iodide, N, N-dimethyl-2-pyrrolidinium ethyltrimethoxysilane chloride, N, N- bromide Dimethyl-2-pyrrolidinium ethyltrimethoxysilane, N, N-dimethyl-2-pyrrolidinium ethyltrimethoxysilane iodide N, N-dimethyl-2-pyrrolidinium propyltrimethoxysilane chloride, N, N-dimethyl-2-pyrrolidinium propyltrimethoxysilane bromide, N, N-dimethyl-2-pyrrolidinium propyl iodide Trimethoxysilane, N, N-dimethyl-2-pyrrolidinium butyltrimethoxysilane chloride, N, N-dimethyl-2-pyrrolidinium butyltrimethoxysilane bromide, N, N-dimethyl-2-pyrrole iodide Dinium butyltrimethoxysilane, N, N-dimethyl-2-pyrrolidinium pentyltrimethoxysilane chloride, N, N-dimethyl-2-pyrrolidinium pentyltrimethoxysilane bromide, N, N-dimethyl iodide 2-pyrrolidinium pentyltrimethoxysilane, N, N-dimethyl-2-pyrrolidinium hexyltrichloride Toxisilane, N, N-dimethyl-2-pyrrolidinium hexyltrimethoxysilane bromide, N, N-dimethyl-2-pyrrolidinium hexyltrimethoxysilane iodide, N, N-dimethyl-2-pyrrolidinium chloride Heptyltrimethoxysilane, N, N-dimethyl-2-pyrrolidinium bromide heptyltrimethoxysilane, N, N-dimethyl-2-pyrrolidinium heptyltrimethoxysilane iodide, N, N-dimethyl-2-chloride Pyrrolidinium octyltrimethoxysilane, N, N-dimethyl-2-pyrrolidinium octyltrimethoxysilane bromide, N, N-dimethyl-2-pyrrolidinium octyltrimethoxysilane iodide, N, N-diethyl chloride 2-pyrrolidinium trimethoxysilane, N, N-diethyl-2-pyrrolidinium bromide Limethoxysilane, N, N-diethyl-2-pyrrolidinium trimethoxysilane iodide, N, N-diethyl-2-pyrrolidinium methyltrimethoxysilane chloride, N, N-diethyl-2-pyrrolidibromide Nitromethyltrimethoxysilane, N, N-diethyl-2-pyrrolidinium methyltrimethoxysilane iodide, N, N-diethyl-2-pyrrolidinium ethyltrimethoxysilane chloride, N, N-diethyl-2 bromide -Pyrrolidinium ethyltrimethoxysilane, N, N-diethyl-2-pyrrolidinium ethyltrimethoxysilane iodide, N, N-diethyl-2-pyrrolidiniumpropyltrimethoxysilane chloride, N, N- bromide Diethyl-2-pyrrolidinium propyl trimethoxysilane, N, N-diethyl-2-pyrrolidinium propyl iodide Trimethoxysilane, N, N-diethyl-2-pyrrolidinium butyltrimethoxysilane chloride, N, N-diethyl-2-pyrrolidinium butyltrimethoxysilane bromide, N, N-diethyl-2-pyrrole iodide Dinium butyltrimethoxysilane, N, N-dipropyl-2-pyrrolidinium trimethoxysilane chloride, N, N-dipropyl-2-pyrrolidinium trimethoxysilane bromide, N, N-dipropyl-2-iodide Pyrrolidinium trimethoxysilane, N, N-dipropyl-2-pyrrolidinium methyltrimethoxysilane chloride, N, N-dipropyl-2-pyrrolidinium methyltrimethoxysilane bromide, N, N-dipropyl iodide 2-pyrrolidinium methyltrimethoxysilane, N, N-dipropyl-2-pyrrolidinium ethyltrichloride chloride Toxisilane, N, N-dipropyl-2-pyrrolidinium ethyltrimethoxysilane bromide, N, N-dipropyl-2-pyrrolidinium ethyltrimethoxysilane iodide, N, N-dipropyl-2-pyrrolidinium chloride Propyltrimethoxysilane, N, N-dipropyl-2-pyrrolidinium propyltrimethoxysilane bromide, N, N-dipropyl-2-pyrrolidinium propyltrimethoxysilane iodide, N, N-dipropyl-2-chloride Pyrrolidinium butyltrimethoxysilane, N, N-dipropyl-2-pyrrolidinium butyltrimethoxysilane bromide, N, N-dipropyl-2-pyrrolidinium butyltrimethoxysilane iodide, N, N-dibutyl chloride -2-pyrrolidinium trimethoxysilane, N, N-dibutyl-2-pyrrolidibromide Umtrimethoxysilane, N, N-dibutyl-2-pyrrolidinium iodide trimethoxysilane, N, N-dibutyl-2-pyrrolidinium methyltrimethoxysilane chloride, N, N-dibutyl-2-pyrrole bromide Dinium methyltrimethoxysilane, N, N-dibutyl-2-pyrrolidinium methyltrimethoxysilane iodide, N, N-dibutyl-2-pyrrolidinium ethyltrimethoxysilane chloride, N, N-dibutyl bromide 2-pyrrolidinium ethyltrimethoxysilane, N, N-dibutyl-2-pyrrolidinium ethyltrimethoxysilane iodide, N, N-dibutyl-2-pyrrolidiniumpropyltrimethoxysilane chloride, N, N bromide -Dibutyl-2-pyrrolidinium propyltrimethoxysilane, N, N-dibutyl-2-pyrrolidinium iodide Propyltrimethoxysilane, N, N-dibutyl-2-pyrrolidinium butyltrimethoxysilane chloride, N, N-dibutyl-2-pyrrolidinium butyltrimethoxysilane bromide, N, N-dibutyl-2 iodide -Pyrrolidinium butyltrimethoxysilane, N, N-dipentyl-2-pyrrolidinium trimethoxysilane chloride, N, N-dipentyl-2-pyrrolidinium trimethoxysilane bromide, N, N-dipentyl iodide- 2-pyrrolidinium trimethoxysilane, N, N-dipentyl-2-pyrrolidinium methyltrimethoxysilane chloride, N, N-dipentyl-2-pyrrolidinium methyltrimethoxysilane bromide, N, N-iodide Dipentyl-2-pyrrolidinium methyltrimethoxysilane, N, N-dipentyl-2-pyrrolidinium chloride Trimethoxysilane, N, N-dipentyl-2-pyrrolidinium bromide ethyltrimethoxysilane, N, N-dipentyl-2-pyrrolidinium ethyltrimethoxysilane iodide, N, N-dipentyl-2-pyrrole chloride Diniumpropyltrimethoxysilane, N, N-dipentyl-2-pyrrolidiniumpropyltrimethoxysilane bromide, N, N-dipentyl-2-pyrrolidiniumpropyltrimethoxysilane iodide,
N, N-dipentyl-2-pyrrolidinium butyltrimethoxysilane chloride, N, N-dipentyl-2-pyrrolidinium butyltrimethoxysilane bromide, N, N-dipentyl-2-pyrrolidinium butyltriiodide Methoxysilane, N, N-dihexyl-2-pyrrolidinium chloride trimethoxysilane, N, N-dihexyl-2-pyrrolidinium trimethoxysilane bromide, N, N-dihexyl-2-pyrrolidinium triiodide Methoxysilane, N, N-dihexyl-2-pyrrolidinium chloride methyltrimethoxysilane, N, N-dihexyl-2-pyrrolidinium methyltrimethoxysilane bromide, iodide N, N-dihexyl-2-pyrrolidi Nitromethyltrimethoxysilane, N, N-dihexyl-2-pyrrolidinium ethyltrimethoxysilane chloride N, N-dihexyl-2-pyrrolidinium ethyltrimethoxysilane bromide, N, N-dihexyl-2-pyrrolidinium ethyltrimethoxysilane iodide, N, N-dihexyl-2-pyrrolidinium propyltrichloride Methoxysilane, N, N-dihexyl-2-pyrrolidinium propyltrimethoxysilane bromide, N, N-dihexyl-2-pyrrolidinium propyltrimethoxysilane iodide, N, N-dihexyl-2-pyrrolidichloride Nitrobutyltrimethoxysilane, N, N-dihexyl-2-pyrrolidinium butyltrimethoxysilane bromide, N, N-dihexyl-2-pyrrolidinium butyltrimethoxysilane iodide, N, N-diheptyl-2 chloride -Pyrrolidinium trimethoxysilane, N, N-diheptyl-2-pyrrolidinium bromide tribromide Toxisilane, N, N-diheptyl-2-pyrrolidinium trimethoxysilane iodide, N, N-diheptyl-2-pyrrolidinium methyltrimethoxysilane chloride, N, N-diheptyl-2-pyrrolidinium methyl bromide Trimethoxysilane, N, N-diheptyl-2-pyrrolidinium methyltrimethoxysilane iodide, N, N-diheptyl-2-pyrrolidinium ethyltrimethoxysilane chloride, N, N-diheptyl-2-pyrrole bromide Dinium ethyltrimethoxysilane, N, N-diheptyl-2-pyrrolidinium ethyltrimethoxysilane iodide, N, N-diheptyl-2-pyrrolidiniumpropyltrimethoxysilane chloride, N, N-diheptyl bromide- 2-pyrrolidiniumpropyltrimethoxysilane, N, N-diheptyl-2-pyrrole iodide Diniumpropyltrimethoxysilane, N, N-diheptyl-2-pyrrolidinium butyltrimethoxysilane chloride, N, N-diheptyl-2-pyrrolidinium butyltrimethoxysilane bromide, N, N-diheptyl iodide 2-pyrrolidinium butyltrimethoxysilane, N, N-dioctyl-2-pyrrolidinium trimethoxysilane chloride, N, N-dioctyl-2-pyrrolidinium trimethoxysilane bromide, N, N-dioctyl iodide 2-pyrrolidinium trimethoxysilane, N, N-dioctyl chloride-2-pyrrolidinium methyltrimethoxysilane, N, N-dioctyl-2-pyrrolidinium methyltrimethoxysilane bromide, N, N iodide -Dioctyl-2-pyrrolidinium methyltrimethoxysilane, N, N-dioctyl-2-pi Lidinium ethyltrimethoxysilane, N, N-dioctyl-2-pyrrolidinium ethyltrimethoxysilane bromide, N, N-dioctyl-2-pyrrolidinium ethyltrimethoxysilane iodide, N, N-dioctyl chloride 2-pyrrolidiniumpropyltrimethoxysilane, N, N-dioctyl-2-pyrrolidiniumpropyltrimethoxysilane bromide, N, N-dioctyl-2-pyrrolidiniumpropyltrimethoxysilane iodide, N, N chloride -Dioctyl-2-pyrrolidinium butyltrimethoxysilane, N, N-dioctyl-2-pyrrolidinium butyltrimethoxysilane bromide, N, N-dioctyl-2-pyrrolidinium butyltrimethoxysilane iodide, chloride N, N-ethylmethyl-2-pyrrolidinium trimethoxysilane, N, bromide -Ethylmethyl-2-pyrrolidinium trimethoxysilane, N, N-ethylmethyl-2-pyrrolidinium trimethoxysilane iodide, N, N-ethylmethyl-2-pyrrolidinium methyltrimethoxysilane chloride, odor N, N-ethylmethyl-2-pyrrolidinium methyltrimethoxysilane, N, N-ethylmethyl-2-pyrrolidinium methyltrimethoxysilane iodide, N, N-ethylmethyl-2-pyrrolidinium chloride Ethyltrimethoxysilane, N, N-ethylmethyl-2-pyrrolidinium bromide ethyltrimethoxysilane, N, N-ethylmethyl-2-pyrrolidinium ethyltrimethoxysilane iodide, N, N-ethylmethyl chloride 2-pyrrolidinium propyl trimethoxysilane, N, N-ethylmethyl-2-pyrrolidinium propylene bromide Rutrimethoxysilane, N, N-ethylmethyl-2-pyrrolidinium propyltrimethoxysilane iodide, N, N-ethylmethyl-2-pyrrolidinium butyltrimethoxysilane chloride, N, N-ethylmethyl bromide 2-pyrrolidinium butyltrimethoxysilane, iodide N, N-ethylmethyl-2-pyrrolidinium butyltrimethoxysilane, N, N-methylpropyl-2-pyrrolidinium trimethoxysilane chloride, bromide N, N-methylpropyl-2-pyrrolidinium trimethoxysilane, iodide N, N-methylpropyl-2-pyrrolidinium trimethoxysilane, N, N-methylpropyl-2-pyrrolidinium methyltrimethoxysilane chloride, N, N-methylpropyl-2-pyrrolidinium methyltrimethoxysilane bromide, N, N-iodide Tylpropyl-2-pyrrolidinium methyltrimethoxysilane, N, N-methylpropyl-2-pyrrolidinium ethyltrimethoxysilane chloride, N, N-methylpropyl-2-pyrrolidinium ethyltrimethoxysilane bromide, iodine N, N-methylpropyl-2-pyrrolidinium ethyltrimethoxysilane, N, N-methylpropyl-2-pyrrolidinium propyltrimethoxysilane chloride, N, N-methylpropyl-2-pyrrolidinium bromide Propyltrimethoxysilane, N, N-methylpropyl-2-pyrrolidinium propyltrimethoxysilane iodide, N, N-methylpropyl-2-pyrrolidinium butyltrimethoxysilane chloride, N, N-methylpropyl bromide -2-pyrrolidinium butyltrimethoxysilane, N, N-methyl iodide Lopyl-2-pyrrolidinium butyltrimethoxysilane, N, N-butylmethyl-2-pyrrolidinium trimethoxysilane chloride, N, N-butylmethyl-2-pyrrolidinium trimethoxysilane bromide, N, N iodide -Butylmethyl-2-pyrrolidinium trimethoxysilane, N, N-butylmethyl-2-pyrrolidinium methyltrimethoxysilane chloride, N, N-butylmethyl-2-pyrrolidinium methyltrimethoxysilane bromide, N iodide , N-butylmethyl-2-pyrrolidinium methyltrimethoxysilane, N, N-butylmethyl-2-pyrrolidinium ethyltrimethoxysilane chloride, N, N-butylmethyl-2-pyrrolidinium ethyltrimethoxysilane bromide, N, N-butylmethyl-2-pyrrolidinium ethyltrimethoxysila iodide N, N-butylmethyl-2-pyrrolidinium propyltrimethoxysilane, N, N-butylmethyl-2-pyrrolidinium propyltrimethoxysilane bromide, N, N-butylmethyl-2-pyrrolidinium iodide Propyltrimethoxysilane, N, N-butylmethyl-2-pyrrolidinium butyltrimethoxysilane chloride, N, N-butylmethyl-2-pyrrolidinium butyltrimethoxysilane bromide, N, N-butylmethyl-2-iodide Pyrrolidinium butyltrimethoxysilane, N, N-ethylpropyl-2-pyrrolidinium trimethoxysilane chloride, N, N-ethylpropyl-2-pyrrolidinium trimethoxysilane bromide, N, N-ethyl iodide Propyl-2-pyrrolidinium trimethoxysilane, N, N-ethylpropyl-2-chloride Loridinium methyltrimethoxysilane, N, N-ethylpropyl-2-pyrrolidinium methyltrimethoxysilane bromide, N, N-ethylpropyl-2-pyrrolidinium methyltrimethoxysilane iodide, N, N chloride -Ethylpropyl-2-pyrrolidinium ethyltrimethoxysilane, N, N-ethylpropyl-2-pyrrolidinium ethyltrimethoxysilane bromide, N, N-ethylpropyl-2-pyrrolidinium ethyltrimethoxy iodide Silane, N, N-ethylpropyl-2-pyrrolidinium propyltrimethoxysilane chloride, N, N-ethylpropyl-2-pyrrolidinium propyltrimethoxysilane bromide, N, N-ethylpropyl-2-iodide Pyrrolidinium propyl trimethoxysilane, N, N-ethylpropyl-2-pyrrole chloride Nitrobutyltrimethoxysilane, N, N-ethylpropyl-2-pyrrolidinium butyltrimethoxysilane bromide, N, N-ethylpropyl-2-pyrrolidinium butyltrimethoxysilane iodide, N, N-butylethyl chloride -2-pyrrolidinium trimethoxysilane, N, N-butylethyl bromide-2-pyrrolidinium trimethoxysilane, N, N-butylethyl iodide-2-pyrrolidinium trimethoxysilane, N, N-butylethyl chloride 2-pyrrolidinium methyltrimethoxysilane, N, N-butylethyl-2-pyrrolidinium methyltrimethoxysilane bromide, N, N-butylethyl-2-pyrrolidinium methyltrimethoxysilane iodide, N, chloride N-butylethyl-2-pyrrolidinium ethyltrimethoxysilane, N, N-bromide Butylethyl-2-pyrrolidinium ethyltrimethoxysilane, iodide N, N-butylethyl-2-pyrrolidinium ethyltrimethoxysilane, N, N-butylethyl-2-pyrrolidiniumpropyltrimethoxysilane chloride, bromide N , N-butylethyl-2-pyrrolidinium propyltrimethoxysilane, N, N-butylethyl-2-pyrrolidinium propyltrimethoxysilane iodide, N, N-butylethyl-2-pyrrolidinium butyltrimethoxysilane chloride, N, N-butylethyl-2-pyrrolidinium butyltrimethoxysilane bromide, N, N-butylethyl-2-pyrrolidinium butyltrimethoxysilane iodide,
N, N-butylpropyl-2-pyrrolidinium trimethoxysilane chloride, N, N-butylpropyl-2-pyrrolidinium trimethoxysilane bromide, N, N-butylpropyl-2-pyrrolidinium iodide iodide Methoxysilane, N, N-butylpropyl-2-pyrrolidinium methyltrimethoxysilane chloride, N, N-butylpropyl-2-pyrrolidinium methyltrimethoxysilane bromide, N, N-butylpropyl-2 iodide -Pyrrolidinium methyltrimethoxysilane, N, N-butylpropyl-2-pyrrolidinium ethyltrimethoxysilane chloride, N, N-butylpropyl-2-pyrrolidinium ethyltrimethoxysilane bromide, N-iodide, N-butylpropyl-2-pyrrolidinium ethyltrimethoxysilane, N, N-butylpropyl-2 chloride Pyrrolidinium propyltrimethoxysilane, N, N-butylpropyl-2-pyrrolidinium propyltrimethoxysilane bromide, N, N-butylpropyl-2-pyrrolidinium propyltrimethoxysilane iodide, N, N chloride -Butylpropyl-2-pyrrolidinium butyltrimethoxysilane, N, N-butylpropyl-2-pyrrolidinium butyltrimethoxysilane bromide, N, N-butylpropyl-2-pyrrolidinium butyltrimethoxy iodide Silane, N, N-dimethyl-3-pyrrolidinium trimethoxysilane chloride, N, N-dimethyl-3-pyrrolidinium trimethoxysilane bromide, N, N-dimethyl-3-pyrrolidinium trimethoxy iodide Silane, N, N-dimethyl-3-pyrrolidinium methyltrimethoxysilane chloride, N-bromide N-dimethyl-3-pyrrolidinium methyltrimethoxysilane, iodide N, N-dimethyl-3-pyrrolidinium methyltrimethoxysilane, N, N-dimethyl-3-pyrrolidinium ethyltrimethoxysilane chloride, odor N, N-dimethyl-3-pyrrolidinium ethyltrimethoxysilane, N, N-dimethyl-3-pyrrolidinium ethyltrimethoxysilane iodide, N, N-dimethyl-3-pyrrolidiniumpropyltrimethoxy chloride Silane, N, N-dimethyl-3-pyrrolidinium propyltrimethoxysilane bromide, N, N-dimethyl-3-pyrrolidinium propyltrimethoxysilane iodide, N, N-dimethyl-3-pyrrolidinium chloride Butyltrimethoxysilane, N, N-dimethyl-3-pyrrolidinium butyltrimethoxysilane bromide, N, N-dimethyl-3-pyrrolidinium butyltrimethoxysilane, N, N-diethyl-3-pyrrolidinium trimethoxysilane chloride, N, N-diethyl-3-pyrrolidinium trimethoxysilane bromide N, N-diethyl-3-pyrrolidinium trimethoxysilane iodide, N, N-diethyl-3-pyrrolidinium methyltrimethoxysilane chloride, N, N-diethyl-3-pyrrolidinium methyltribromide bromide Methoxysilane, N, N-diethyl-3-pyrrolidinium methyltrimethoxysilane iodide, N, N-diethyl-3-pyrrolidinium ethyltrimethoxysilane chloride, N, N-diethyl-3-pyrrolidibromide Nitroethyltrimethoxysilane, N, N-diethyl-3-pyrrolidinium ethyltrimethoxysilane iodide, N, N-diethyl chloride -3-pyrrolidinium propyltrimethoxysilane, N, N-diethyl-3-pyrrolidinium propyltrimethoxysilane bromide, iodide N, N-diethyl-3-pyrrolidinium propyltrimethoxysilane, N, chloride N-diethyl-3-pyrrolidinium butyltrimethoxysilane, N, N-diethyl-3-pyrrolidinium butyltrimethoxysilane bromide, N, N-diethyl-3-pyrrolidinium butyltrimethoxysilane iodide, N, N-ethylmethyl-3-pyrrolidinium trimethoxysilane chloride, N, N-ethylmethyl-3-pyrrolidinium trimethoxysilane bromide, N, N-ethylmethyl-3-pyrrolidinium iodide iodide Methoxysilane, N, N-ethylmethyl-3-pyrrolidinium chloride methyltrimethoxysilane, N, N-bromide Rumethyl-3-pyrrolidinium methyltrimethoxysilane, N, N-ethylmethyl-3-pyrrolidinium methyltrimethoxysilane iodide, N, N-ethylmethyl-3-pyrrolidinium ethyltrimethoxysilane chloride, odor N, N-ethylmethyl-3-pyrrolidinium ethyltrimethoxysilane, N, N-ethylmethyl-3-pyrrolidinium ethyltrimethoxysilane iodide, N, N-ethylmethyl-3-pyrrolidinium chloride Propyltrimethoxysilane, N, N-ethylmethyl-3-pyrrolidinium propyltrimethoxysilane bromide, N, N-ethylmethyl-3-pyrrolidinium propyltrimethoxysilane iodide, N, N-ethylmethyl chloride -3-pyrrolidinium butyltrimethoxysilane, N, N-ethylmethyl bromide-3-pyrrolidinyl bromide Umbutyltrimethoxysilane, N, N-ethylmethyl-3-pyrrolidinium butyltrimethoxysilane iodide, N, N-dimethyl-2-piperidiniumtrimethoxysilane chloride, N, N-dimethyl-2 bromide -Piperidinium trimethoxysilane, N, N-dimethyl-2-piperidinium trimethoxysilane iodide, N, N-dimethyl-2-piperidinium methyltrimethoxysilane chloride, N, N-dimethyl bromide 2-piperidinium methyltrimethoxysilane, iodide N, N-dimethyl-2-piperidinium methyltrimethoxysilane, N, N-dimethyl-2-piperidinium ethyltrimethoxysilane chloride, bromide N, N -Dimethyl-2-piperidinium ethyltrimethoxysilane, N, N-dimethyl-2-piperidinium ethyl iodide Methoxysilane, N, N-dimethyl-2-piperidiniumpropyltrimethoxysilane chloride, N, N-dimethyl-2-piperidiniumpropyltrimethoxysilane bromide, iodide N, N-dimethyl-2-piperidi N-propyltrimethoxysilane, N, N-dimethyl-2-piperidinium butyltrimethoxysilane chloride, N, N-dimethyl-2-piperidinium butyltrimethoxysilane bromide, N, N-dimethyl-2 iodide -Piperidinium butyltrimethoxysilane, N, N-diethyl-2-piperidinium trimethoxysilane chloride, N, N-diethyl-2-piperidinium trimethoxysilane bromide, N, N-diethyl iodide 2-piperidinium trimethoxysilane, N, N-diethyl-2-piperidinium methyltrimethoxysilane chloride N, N-diethyl-2-piperidinium methyltrimethoxysilane bromide, N, N-diethyl-2-piperidinium methyltrimethoxysilane iodide, N, N-diethyl-2-piperidinium chloride Ethyltrimethoxysilane, N, N-diethyl-2-piperidinium bromide ethyltrimethoxysilane, N, N-diethyl-2-piperidinium ethyltrimethoxysilane iodide, N, N-diethyl-2-chloride Piperidiniumpropyltrimethoxysilane, N, N-diethyl-2-piperidiniumpropyltrimethoxysilane bromide, N, N-diethyl-2-piperidiniumpropyltrimethoxysilane iodide, N, N-diethyl chloride 2-piperidinium butyltrimethoxysilane, N, N-diethyl-2-piperidinium butyltrimethoxy bromide Sisilane, N, N-diethyl-2-piperidinium butyltrimethoxysilane iodide, N, N-ethylmethyl-2-piperidinium trimethoxysilane chloride, N, N-ethylmethyl-2-piperidibromide Nitrimethoxysilane, N, N-ethylmethyl-2-piperidinium trimethoxysilane iodide, N, N-ethylmethyl-2-piperidinium methyltrimethoxysilane chloride, N, N-ethylmethyl bromide 2-piperidinium methyltrimethoxysilane, iodide N, N-ethylmethyl-2-piperidinium methyltrimethoxysilane, N, N-ethylmethyl-2-piperidinium ethyltrimethoxysilane chloride, bromide N , N-ethylmethyl-2-piperidinium ethyltrimethoxysilane, iodide N, N-ethylmethyl-2-piperidini Methyltrimethoxysilane, N, N-ethylmethyl-2-piperidiniumpropyltrimethoxysilane chloride, N, N-ethylmethyl-2-piperidiniumpropyltrimethoxysilane bromide, N, N-ethyl iodide Methyl-2-piperidiniumpropyltrimethoxysilane, N, N-ethylmethyl-2-piperidinium butyltrimethoxysilane chloride, N, N-ethylmethyl-2-piperidinium butyltrimethoxysilane bromide, iodine N, N-ethylmethyl-2-piperidinium butyltrimethoxysilane, N, N-dimethyl-3-piperidinium trimethoxysilane chloride, N, N-dimethyl-3-piperidinium trimethoxysilane bromide N, N-dimethyl-3-piperidinium trimethoxysilane iodide, N, N-dimethyl-3 chloride Piperidinium methyltrimethoxysilane, bromide N, N-dimethyl-3-piperidinium methyltrimethoxysilane,
N, N-dimethyl-3-piperidinium methyltrimethoxysilane iodide, N, N-dimethyl-3-piperidinium ethyltrimethoxysilane chloride, N, N-dimethyl-3-piperidinium ethyltribromide Methoxysilane, N, N-dimethyl-3-piperidinium ethyltrimethoxysilane iodide, N, N-dimethyl-3-piperidiniumpropyltrimethoxysilane chloride, N, N-dimethyl-3-piperidibromide Ni-propyltrimethoxysilane, N, N-dimethyl-3-piperidiniumpropyltrimethoxysilane iodide, N, N-dimethyl-3-piperidiniumbutyltrimethoxysilane chloride, N, N-dimethyl-3 bromide -Piperidinium butyltrimethoxysilane, N, N-dimethyl-3-piperidinium butyltrimethoxy iodide Orchid, N, N-diethyl-3-piperidinium trimethoxysilane chloride, N, N-diethyl-3-piperidinium trimethoxysilane bromide, N, N-diethyl-3-piperidinium trimethoxy iodide Silane, N, N-diethyl-3-piperidinium methyltrimethoxysilane chloride, N, N-diethyl-3-piperidinium methyltrimethoxysilane bromide, N, N-diethyl-3-piperidinium iodide Methyltrimethoxysilane, N, N-diethyl-3-piperidinium ethyltrimethoxysilane chloride, N, N-diethyl-3-piperidinium ethyltrimethoxysilane bromide, N, N-diethyl-3-iodide Piperidinium ethyltrimethoxysilane, N, N-diethyl-3-piperidiniumpropyltrimethoxysilane chloride, N, bromide -Diethyl-3-piperidiniumpropyltrimethoxysilane, iodide N, N-diethyl-3-piperidiniumpropyltrimethoxysilane, N, N-diethyl-3-piperidiniumbutyltrimethoxysilane chloride, bromide N, N-diethyl-3-piperidinium butyltrimethoxysilane, iodide N, N-diethyl-3-piperidiniumbutyltrimethoxysilane, N, N-ethylmethyl-3-piperidiniumtrimethoxysilane chloride N, N-ethylmethyl-3-piperidinium trimethoxysilane bromide, N, N-ethylmethyl-3-piperidinium trimethoxysilane iodide, N, N-ethylmethyl-3-piperidinium chloride Methyltrimethoxysilane, N, N-ethylmethyl-3-piperidinium bromide methyltrimethoxysilane, iodine N, N-ethylmethyl-3-piperidinium methyltrimethoxysilane, N, N-ethylmethyl-3-piperidinium ethyltrimethoxysilane, N, N-ethylmethyl-3-piperidinium bromide Ethyltrimethoxysilane, N, N-ethylmethyl-3-piperidinium ethyltrimethoxysilane iodide, N, N-ethylmethyl-3-piperidiniumpropyltrimethoxysilane chloride, N, N-ethylmethyl bromide -3-piperidiniumpropyltrimethoxysilane, iodide N, N-ethylmethyl-3-piperidiniumpropyltrimethoxysilane, N, N-ethylmethyl-3-piperidiniumbutyltrimethoxysilane chloride, bromide N, N-ethylmethyl-3-piperidinium butyltrimethoxysilane, N, N-ethylmethyl iodide- Piperidinium butyltrimethoxysilane, N, N-dimethyl-4-piperidinium trimethoxysilane chloride, N, N-dimethyl-4-piperidinium trimethoxysilane bromide, N, N-dimethyl iodide 4-piperidinium trimethoxysilane, N, N-dimethyl-4-piperidinium methyltrimethoxysilane chloride, N, N-dimethyl-4-piperidinium methyltrimethoxysilane bromide, N, N-iodide Dimethyl-4-piperidinium methyltrimethoxysilane, N, N-dimethyl-4-piperidinium ethyltrimethoxysilane chloride, N, N-dimethyl-4-piperidinium ethyltrimethoxysilane bromide, N iodide , N-dimethyl-4-piperidinium ethyltrimethoxysilane, N, N-dimethyl-4-piperidinium chloride Propyltrimethoxysilane, N, N-dimethyl-4-piperidiniumpropyltrimethoxysilane bromide, N, N-dimethyl-4-piperidiniumpropyltrimethoxysilane iodide, N, N-dimethyl-4 chloride -Piperidinium butyltrimethoxysilane, N, N-dimethyl-4-piperidinium butyltrimethoxysilane bromide, N, N-dimethyl-4-piperidinium butyltrimethoxysilane iodide, N, N- Diethyl-4-piperidinium trimethoxysilane, N, N-diethyl-4-piperidinium trimethoxysilane bromide, N, N-diethyl-4-piperidinium trimethoxysilane iodide, N, N-chloride Diethyl-4-piperidinium methyltrimethoxysilane, N, N-diethyl-4-piperidinium methyltrimethobromide Xisilane, N, N-diethyl-4-piperidinium methyltrimethoxysilane iodide, N, N-diethyl-4-piperidinium ethyltrimethoxysilane chloride, N, N-diethyl-4-piperidinium bromide Ethyltrimethoxysilane, N, N-diethyl-4-piperidinium iodide, ethyltrimethoxysilane, N, N-diethyl-4-piperidiniumpropyltrimethoxysilane chloride, N, N-diethyl-4-bromide Piperidiniumpropyltrimethoxysilane, N, N-diethyl-4-piperidiniumpropyltrimethoxysilane iodide, N, N-diethyl-4-piperidiniumbutyltrimethoxysilane chloride, N, N-diethyl bromide -4-piperidinium butyltrimethoxysilane, N, N-diethyl-4-piperidinium butyl iodide Rimethoxysilane, N, N-ethylmethyl-4-piperidinium trimethoxysilane chloride, N, N-ethylmethyl-4-piperidinium trimethoxysilane bromide, N, N-ethylmethyl-4-iodide Piperidinium trimethoxysilane,
N, N-ethylmethyl-4-piperidinium methyltrimethoxysilane chloride, N, N-ethylmethyl-4-piperidinium methyltrimethoxysilane bromide, iodide N, N-ethylmethyl-4-piperidi Niummethyltrimethoxysilane, N, N-ethylmethyl-4-piperidinium ethyltrimethoxysilane chloride, N, N-ethylmethyl-4-piperidinium ethyltrimethoxysilane bromide, N, N-ethyl iodide Methyl-4-piperidinium ethyltrimethoxysilane, N, N-ethylmethyl-4-piperidiniumpropyltrimethoxysilane chloride, N, N-ethylmethyl-4-piperidiniumpropyltrimethoxysilane bromide, iodine N, N-ethylmethyl-4-piperidiniumpropyltrimethoxysilane, N, N-ethylmethyl chloride 4-piperidinium butyltrimethoxysilane, N, N-ethylmethyl bromide-4-piperidinium butyltrimethoxysilane, N, N-ethylmethyl-4-piperidinium butyltrimethoxysilane iodide, N chloride N, N-dimethyl-2-pyrrolinium trimethoxysilane, N, N-dimethyl-2-pyrrolium trimethoxysilane bromide, N, N-dimethyl-2-pyrrolium trimethoxysilane iodide, N, N-chloride Dimethyl-2-pyrroliniummethyltrimethoxysilane, N, N-dimethyl-2-pyrroliniummethyltrimethoxysilane bromide, N, N-dimethyl-2-pyrroliummethyltrimethoxysilane iodide, N, N-chloride Dimethyl-2-pyrroliniumethyltrimethoxysilane, N, N-dimethyl-2-pyrroliniumethyl bromide Limethoxysilane, N, N-dimethyl-2-pyrrolium ethyltrimethoxysilane iodide, N, N-dimethyl-2-pyrroliumpropyltrimethoxysilane chloride, N, N-dimethyl-2-pyrroliumpropyl bromide Trimethoxysilane, N, N-dimethyl-2-pyrroliumpropyltrimethoxysilane iodide, N, N-dimethyl-2-pyrroliumbutyltrimethoxysilane chloride, N, N-dimethyl-2-pyrroliumbutyl bromide Trimethoxysilane, N, N-dimethyl-2-pyrrolinium butyltrimethoxysilane iodide, N, N-diethyl-2-pyrrolium trimethoxysilane chloride, N, N-diethyl-2-pyrrolinium trimethoxy bromide Silane, N, N-diethyl-2-pyrrolium trimethoxysilane iodide, N, N-chloride Diethyl-2-pyrroliniummethyltrimethoxysilane, N, N-diethyl-2-pyrroliummethyltrimethoxysilane bromide, N, N-diethyl-2-pyrroliummethyltrimethoxysilane iodide, N, N-chloride Diethyl-2-pyrroliniumethyltrimethoxysilane, N, N-diethyl-2-pyrroliumethyltrimethoxysilane bromide, N, N-diethyl-2-pyrroliumethyltrimethoxysilane iodide, N, N-chloride Diethyl-2-pyrroliumpropyltrimethoxysilane, N, N-diethyl-2-pyrroliumpropyltrimethoxysilane bromide, N, N-diethyl-2-pyrroliumpropyltrimethoxysilane iodide, N, N-chloride Diethyl-2-pyrrolium butyltrimethoxysilane, N, N-diethyl-2-bromide Rolinium butyltrimethoxysilane, N, N-diethyl-2-pyrroliumbutyltrimethoxysilane iodide, N, N-ethylmethyl-2-pyrroliumtrimethoxysilane chloride, N, N-ethylmethyl-2 bromide -Pyrrolium trimethoxysilane, N, N-ethylmethyl-2-pyrrolium trimethoxysilane iodide, N, N-ethylmethyl-2-pyrrolium methyltrimethoxysilane chloride, N, N-ethylmethyl bromide- 2-pyrroliniummethyltrimethoxysilane, N, N-ethylmethyl-2-pyrroliummethyltrimethoxysilane iodide, N, N-ethylmethyl-2-pyrroliumethyltrimethoxysilane chloride, N, N-bromide Ethylmethyl-2-pyrroliniumethyltrimethoxysilane, N, N-ethylmethyl-2-iodide Lori bromide ethyltrimethoxysilane, chloride N, N-ethylmethyl-2-pyrrolidone hexafluorophosphate trimethoxysilane,
N, N-ethylmethyl-2-pyrroliumpropyltrimethoxysilane bromide, N, N-ethylmethyl-2-pyrroliumpropyltrimethoxysilane iodide, N, N-ethylmethyl-2-pyrroliumbutyltrichloride Methoxysilane, N, N-ethylmethyl-2-pyrrolium butyltrimethoxysilane bromide, N, N-ethylmethyl-2-pyrrolium butyltrimethoxysilane iodide, N, N-dimethyl-3-pyrrolium chloride Trimethoxysilane, N, N-dimethyl-3-pyrrolium trimethoxysilane bromide, N, N-dimethyl-3-pyrrolium trimethoxysilane iodide, N, N-dimethyl-3-pyrrolium methyltrimethoxy chloride Silane, N, N-dimethyl-3-pyrroliniummethyltrimethoxysilane bromide, N, N-iodide Methyl-3-pyrroliniummethyltrimethoxysilane, N, N-dimethyl-3-pyrroliumethyltrimethoxysilane chloride, N, N-dimethyl-3-pyrroliumethyltrimethoxysilane bromide, N, N-iodide Dimethyl-3-pyrroliniumethyltrimethoxysilane, N, N-dimethyl-3-pyrroliumpropyltrimethoxysilane chloride, N, N-dimethyl-3-pyrroliumpropyltrimethoxysilane bromide, N, N-iodide Dimethyl-3-pyrrolinylpropyltrimethoxysilane, N, N-dimethyl-3-pyrroliumbutyltrimethoxysilane chloride, N, N-dimethyl-3-pyrroliumbutyltrimethoxysilane bromide, N, N-iodide Dimethyl-3-pyrrolium butyltrimethoxysilane, N, N-diethyl-3-chloride Rolinium trimethoxysilane, N, N-diethyl-3-pyrrolium trimethoxysilane bromide, N, N-diethyl-3-pyrrolium trimethoxysilane iodide, N, N-diethyl-3-pyrrolium methyl chloride Trimethoxysilane, N, N-diethyl-3-pyrroliummethyltrimethoxysilane bromide, N, N-diethyl-3-pyrroliummethyltrimethoxysilane iodide, N, N-diethyl-3-pyrroliumethyl chloride Trimethoxysilane, N, N-diethyl-3-pyrrolium ethyltrimethoxysilane bromide, N, N-diethyl-3-pyrrolium ethyltrimethoxysilane iodide, N, N-diethyl-3-pyrroliumpropyl chloride Trimethoxysilane, N, N-diethyl-3-pyrroliumpropyltrimethoxysilane bromide N, N-diethyl-3-pyrroliumpropyltrimethoxysilane iodide, N, N-diethyl-3-pyrroliumbutyltrimethoxysilane chloride, N, N-diethyl-3-pyrroliumbutyltrimethoxysilane bromide N, N-diethyl-3-pyrroliumbutyltrimethoxysilane iodide, N, N-ethylmethyl-3-pyrroliumtrimethoxysilane chloride, N, N-ethylmethyl-3-pyrroliumtrimethoxysilane bromide N, N-ethylmethyl-3-pyrroliumtrimethoxysilane iodide, N, N-ethylmethyl-3-pyrroliummethyltrimethoxysilane chloride, N, N-ethylmethyl-3-pyrroliummethyltribromide bromide Methoxysilane, N, N-ethylmethyl-3-pyrrolium iodide, trimethoxysilane iodide, N, chloride -Ethylmethyl-3-pyrroliniumethyltrimethoxysilane, N, N-ethylmethyl-3-pyrroliumethyltrimethoxysilane bromide, N, N-ethylmethyl-3-pyrroliumethyltrimethoxysilane iodide, chloride N, N-ethylmethyl-3-pyrroliumpropyltrimethoxysilane, N, N-ethylmethyl-3-pyrroliumpropyltrimethoxysilane bromide, N, N-ethylmethyl-3-pyrroliumpropyltrimethoxy iodide Silane, N, N-ethylmethyl-3-pyrroliumbutyltrimethoxysilane chloride, N, N-ethylmethyl-3-pyrroliumbutyltrimethoxysilane bromide, N, N-ethylmethyl-3-pyrrolinium iodide Butyltrimethoxysilane, N, N-dimethyl-2,3-dihydro-1H-2-chloride Rolinium trimethoxysilane, N, N-dimethyl-2,3-dihydro-1H-2-pyrrolinium bromide trimethoxysilane, N, N-dimethyl-2,3-dihydro-1H-2-pyrrolinium iodide Trimethoxysilane, N, N-dimethyl-2,3-dihydro-1H-2-pyrroliummethyltrimethoxysilane chloride, N, N-dimethyl-2,3-dihydro-1H-2-pyrroliniummethyltribromide Methoxysilane, N, N-dimethyl-2,3-dihydro-1H-2-pyrroliummethyltrimethoxysilane iodide, N, N-dimethyl-2,3-dihydro-1H-3-pyrroliumtrimethoxysilane chloride N, N-dimethyl-2,3-dihydro-1H-3-pyrrolinium trimethoxysilane bromide, N, N-dimethyl-2,3-dihydroiodide -1H-3-pyrrolinium trimethoxysilane, N, N-dimethyl-2,3-dihydro-1 chloride-1H-3-pyrrolium methyltrimethoxysilane, N, N-dimethyl-2,3-dihydro-1H bromide -3-pyrroliniummethyltrimethoxysilane, N, N-dimethyl-2,3-dihydro-1H iodide, N-N-dimethyl-2,3-dihydro-1H- chloride 4-pyrrolinium trimethoxysilane, N, N-dimethyl-2,3-dihydro-1H-4-bromonium trimethoxysilane bromide, N, N-dimethyl-2,3-dihydro-1H-4-iodide iodide Pyrrolium trimethoxysilane, N, N-dimethyl-2,3-dihydro-1H-4-pyrroliummethyltrimethoxysilane chloride, N, N-dimethyl bromide 2,3-dihydro-1H-4-pyrroliummethyltrimethoxysilane, iodide N, N-dimethyl-2,3-dihydro-1H-4-pyrroliummethyltrimethoxysilane, N, N-dimethyl-2 chloride , 3-Dihydro-1H-5-pyrroliumtrimethoxysilane, N, N-dimethyl-2,3-dihydro-1H-5-pyrroliumtrimethoxysilane bromide, N, N-dimethyl-2,3 iodide -Dihydro-1H-5-pyrrolinium trimethoxysilane, N, N-dimethyl-2,3-dihydro-1H-1 -pyrroliummethyltrimethoxysilane chloride, N, N-dimethyl-2,3-dihydrobromide -1H-5-pyrroliniummethyltrimethoxysilane, N, N-dimethyl-2,3-dihydro-1iodo-1H-5-pyrroliniummethyltrimethoxysilane N, N-dimethyl-2,5-dihydro-1H-2-pyrrolinium trimethoxysilane, N, N-dimethyl-2,5-dihydro-1H-2-pyrrolinium trimethoxysilane bromide, iodine N, N-dimethyl-2,5-dihydro-1H-2-pyrrolinium trimethoxysilane, N, N-dimethyl-2,5-dihydro-1H-2-pyrroliummethyltrimethoxysilane chloride, N-bromide , N-dimethyl-2,5-dihydro-1H-2-pyrroliummethyltrimethoxysilane, N, N-dimethyl-2,5-dihydro-1H-2-pyrroliummethyltrimethoxysilane iodide, N, chloride N-dimethyl-2,5-dihydro-1H-3-pyrrolinium trimethoxysilane, N, N-dimethyl-2,5-dihydro-1H-3-pyrrolinium tribromide Methoxysilane, N, N-dimethyl-2,5-dihydro-1H-3-pyrroliumtrimethoxysilane iodide, N, N-dimethyl-2,5-dihydro-1H-3-pyrroliummethyltrimethoxysilane chloride N, N-dimethyl-2,5-dihydro-1H-3-pyrroliummethyltrimethoxysilane bromide, N, N-dimethyl-2,5-dihydro-1H-3-pyrroliummethyltrimethoxysilane iodide N, N-dimethyl-1,2,3,4-tetrahydro-2-pyridinium trimethoxysilane chloride, N, N-dimethyl-1,2,3,4-tetrahydro-2-pyridinium trimethoxysilane bromide, N, N-dimethyl-1,2,3,4-tetrahydro-2-pyridinium trimethoxysilane iodide, N, N-dimethyl-1,2,3, chloride -Tetrahydro-2-pyridinium methyltrimethoxysilane, N, N-dimethyl-1,2,3,4-tetrahydro-2-pyridiniummethyltrimethoxysilane bromide, N, N-dimethyl-1,2,3 iodide , 4-Tetrahydro-2-pyridinium methyltrimethoxysilane, N, N-dimethyl-1,2,3,4-tetrahydro-3-pyridiniumtrimethoxysilane chloride, N, N-dimethyl-1,2,3 bromide , 4-Tetrahydro-3-pyridinium trimethoxysilane, N, N-dimethyl-1,2,3,4-tetrahydro-3-pyridinium trimethoxysilane iodide, N, N-dimethyl-1,2,3 chloride 4-tetrahydro-3-pyridinium methyltrimethoxysilane, N, N-dimethyl-1,2,3,4-tetrahydro-3-bromide Lizinium methyltrimethoxysilane, N, N-dimethyl-1,2,3,4-tetrahydro-3-pyridiniummethyltrimethoxysilane iodide, N, N-dimethyl-1,2,3,4-tetrahydro-chloride 4-pyridinium trimethoxysilane, brominated N, N-dimethyl-1,2,3,4-tetrahydro-4-pyridinium trimethoxysilane, iodide N, N-dimethyl-1,2,3,4-tetrahydro- 4-pyridinium trimethoxysilane, N, N-dimethyl-1,2,3,4-tetrahydrochloride-4-pyridinium methyltrimethoxysilane chloride, N, N-dimethyl-1,2,3,4-tetrahydro-bromide 4-pyridinium methyltrimethoxysilane,
N, N-dimethyl-1,2,3,4-tetrahydro-4-pyridiniummethyltrimethoxysilane iodide, N, N-dimethyl-1,2,3,4-tetrahydro-5-pyridiniumtrimethoxysilane chloride, N, N-dimethyl-1,2,3,4-tetrahydro-5-pyridinium trimethoxysilane bromide, N, N-dimethyl-1,2,3,4-tetrahydro-5-pyridinium trimethoxysilane iodide, N, N-dimethyl-1,2,3,4-tetrahydro-5-pyridinium methyltrimethoxysilane chloride, N, N-dimethyl-1,2,3,4-tetrahydro-5-pyridiniummethyltrimethoxysilane bromide N, N-dimethyl-1,2,3,4-tetrahydro-5-pyridiniummethyltrimethoxysilane iodide, N, N-dimethyl chloride 1,2,3,4-tetrahydro-6-pyridinium trimethoxysilane, N, N-dimethyl-1,2,3,4-tetrahydro-6-pyridinium trimethoxysilane bromide, N, N-dimethyl iodide 1,2,3,4-tetrahydro-6-pyridinium trimethoxysilane, N, N-dimethyl-1,2,3,4-tetrahydro-6-pyridiniummethyltrimethoxysilane chloride, N, N-dimethyl-bromide 1,2,3,4-tetrahydro-6-pyridinium methyltrimethoxysilane, iodide N, N-dimethyl-1,2,3,4-tetrahydro-6-pyridiniummethyltrimethoxysilane, N, N-dimethyl chloride -1,2,5,6-tetrahydro-2-pyridinium trimethoxysilane, N, N-dimethyl-1,2,5,6-tetrahydride bromide 2-pyridinium trimethoxysilane, iodide N, N-dimethyl-1,2,5,6-tetrahydro-2-pyridinium trimethoxysilane, chloride N, N-dimethyl-1,2,5,6-tetrahydro- 2-pyridiniummethyltrimethoxysilane, N, N-dimethyl-1,2,5,6-tetrahydro-2-pyridiniummethyltrimethoxysilane bromide, iodide N, N-dimethyl-1,2,5,6- Tetrahydro-2-pyridinium methyltrimethoxysilane, N, N-dimethyl-1,2,5,6-tetrahydro-3-pyridiniumtrimethoxysilane, N, N-dimethyl-1,2,5,6-bromide Tetrahydro-3-pyridinium trimethoxysilane, iodide N, N-dimethyl-1,2,5,6-tetrahydro-3-pyridinium trimeth Xylsilane, N, N-dimethyl-1,2,5,6-tetrahydro-3-pyridiniummethyltrimethoxysilane chloride, N, N-dimethyl-1,2,5,6-tetrahydro-3-pyridiniummethyltribromide bromide Methoxysilane, iodide N, N-dimethyl-1,2,5,6-tetrahydro-3-pyridiniummethyltrimethoxysilane, N, N-dimethyl-1,2,5,6-tetrahydro-4-pyridinium trichloride Methoxysilane, N, N-dimethyl-1,2,5,6-tetrahydro-4-pyridinium trimethoxybromide, N, N-dimethyl-1,2,5,6-tetrahydro-4-pyridinium triiodide Methoxysilane, N, N-dimethyl-1,2,5,6-tetrahydro-4-pyridiniummethyltrimethoxysilane chloride, N, N bromide Dimethyl-1,2,5,6-tetrahydro-4-pyridinium methyltrimethoxysilane, iodinated N, N-dimethyl-1,2,5,6-tetrahydro-4-pyridiniummethyltrimethoxysilane, N, N chloride -Dimethyl-1,2,5,6-tetrahydro-5-pyridinium trimethoxysilane, N, N-dimethyl-1,2,5,6-tetrahydro-5-pyridinium trimethoxysilane bromide, N, N iodide -Dimethyl-1,2,5,6-tetrahydro-5-pyridinium trimethoxysilane, N, N-dimethyl-1,2,5,6-tetrahydro-5-pyridiniummethyltrimethoxysilane chloride, N, N bromide -Dimethyl-1,2,5,6-tetrahydro-5-pyridiniummethyltrimethoxysilane, iodide N, N-dimethyl-1,2, , 6-Tetrahydro-5-pyridinium methyltrimethoxysilane, N, N-dimethyl-1,2,5,6-tetrahydro-6-pyridiniumtrimethoxysilane chloride, N, N-dimethyl-1,2,5 bromide , 6-Tetrahydro-6-pyridinium trimethoxysilane, N, N-dimethyl-1,2,5,6-tetrahydro-6-pyridinium trimethoxysilane iodide, N, N-dimethyl-1,2,5, chloride 6-tetrahydro-6-pyridinium methyltrimethoxysilane, N, N-dimethyl-1,2,5,6-tetrahydro-6-pyridiniummethyltrimethoxysilane bromide, iodide N, N-dimethyl-1,2, 5,6-tetrahydro-6-pyridinium methyltrimethoxysilane, N, N-dimethyl-1,2-dihydro-2-pyridinium chloride Mutrimethoxysilane, N, N-dimethyl-1,2-dihydro-2-pyridinium trimethoxysilane bromide, N, N-dimethyl-1,2-dihydro-2-pyridinium trimethoxysilane iodide, N, N chloride -Dimethyl-1,2-dihydro-2-pyridiniummethyltrimethoxysilane, N, N-dimethyl-1,2-dihydro-2-pyridiniummethyltrimethoxysilane bromide, N, N-dimethyl-1, iodide -Dihydro-2-pyridinium methyltrimethoxysilane, N, N-dimethyl-1,2-dihydro-3-pyridiniumtrimethoxysilane chloride, N, N-dimethyl-1,2-dihydro-3-pyridinium trimethoxy bromide Silane, N, N-dimethyl-1,2-dihydro-3-pyridinium trimethoxysilane iodide, N, N-chloride Methyl-1,2-dihydro-3-pyridiniummethyltrimethoxysilane, N, N-dimethyl-1,2-dihydro-3-pyridiniummethyltrimethoxysilane bromide, N, N-dimethyl-1,2-iodide Dihydro-3-pyridinium methyltrimethoxysilane, N, N-dimethyl-1,2-dihydro-4-pyridiniumtrimethoxysilane chloride, N, N-dimethyl-1,2-dihydro-4-pyridiniumtrimethoxysilane bromide N, N-dimethyl-1,2-dihydro-4-pyridinium trimethoxysilane iodide, N, N-dimethyl-1,2-dihydro-4-pyridiniummethyltrimethoxysilane chloride, N, N-dimethyl bromide -1,2-dihydro-4-pyridinium methyltrimethoxysilane, iodide N, N-dimethyl-1,2-dihy Rho-4-pyridinium methyltrimethoxysilane, N, N-dimethyl-1,2-dihydro-5-pyridiniumtrimethoxysilane chloride, N, N-dimethyl-1,2-dihydro-5-pyridiniumtrimethoxysilane bromide N, N-dimethyl-1,2-dihydro-5-pyridinium trimethoxysilane iodide, N, N-dimethyl-1,2-dihydro-5-pyridiniummethyltrimethoxysilane chloride, N, N-dimethyl bromide -1,2-dihydro-5-pyridinium methyltrimethoxysilane, iodide N, N-dimethyl-1,2-dihydro-5-pyridinium) methyltrimethoxysilane, N, N-dimethyl-1,2-dihydrochloride -6-pyridinium trimethoxysilane, N, N-dimethyl-1,2-dihydro-6-pyridinium trimethobromide Xisilane, N, N-dimethyl-1,2-dihydro-6-pyridinium trimethoxysilane iodide, N, N-dimethyl-1,2-dihydro-6-pyridiniummethyltrimethoxysilane chloride, N, N-bromide Dimethyl-1,2-dihydro-6-pyridinium methyltrimethoxysilane, N, N-dimethyl-1,2-dihydro-6-pyridiniummethyltrimethoxysilane iodide, N, N-dimethyl-1H, 3H-2 chloride -Pyridinium trimethoxysilane, N, N-dimethyl-1H, 3H-2-pyridinium trimethoxysilane bromide, N, N-dimethyl-1H, 3H-2-pyridinium trimethoxysilane iodide, N, N-dimethyl chloride -1H, 3H-2-pyridinium methyltrimethoxysilane, N, N-dimethyl-1H, 3H-2-pi Diniummethyltrimethoxysilane, N, N-dimethyl-1H, 3H-2-pyridiniummethyltrimethoxysilane iodide, N, N-dimethyl-1H, 3H-3-pyridiniumtrimethoxysilane chloride, N, N bromide -Dimethyl-1H, 3H-3-pyridinium trimethoxysilane, N, N-dimethyl-1H, 3H-3-pyridinium trimethoxysilane iodide, N, N-dimethyl-1H, 3H-3-pyridinium methyltrimethoxy chloride Silane, N, N-dimethyl-1H, 3H-3-pyridiniummethyltrimethoxysilane bromide, N, N-dimethyl-1H, 3H-3-pyridiniummethyltrimethoxysilane iodide, N, N-dimethyl-1H chloride , 3H-4-pyridinium trimethoxysilane, N, N-dimethyl-1H, 3H-4-pibromide Diniumtrimethoxysilane, N, N-dimethyl-1H, 3H-4-pyridiniumtrimethoxysilane iodide, N, N-dimethyl-1H, 3H-4-pyridiniummethyltrimethoxysilane chloride, N, N-bromide Dimethyl-1H, 3H-4-pyridinium methyltrimethoxysilane, N, N-dimethyl-1H, 3H-4-pyridiniummethyltrimethoxysilane iodide, N, N-dimethyl-2-pyrrolidinium phenyltrimethoxysilane chloride N, N-dimethyl-2-pyrrolidinium phenyltrimethoxysilane bromide, N, N-dimethyl-2-pyrrolidinium phenyltrimethoxysilane iodide, N, N-diethyl-2-pyrrolidinium phenyl chloride Trimethoxysilane, N, N-diethyl-2-pyrrolidinium bromide phenyltrimethoxysilane Run, N, N-diethyl-2-pyrrolidinium phenyltrimethoxysilane iodide, N, N-ethylmethyl-2-pyrrolidinium phenyltrimethoxysilane chloride, N, N-ethylmethyl-2-pyrrole bromide Dinium phenyltrimethoxysilane, N, N-ethylmethyl-2-pyrrolidinium phenyltrimethoxysilane iodide, N, N-dimethyl-3-pyrrolidinium phenyltrimethoxysilane chloride, N, N-dimethyl bromide -3-pyrrolidinium phenyltrimethoxysilane, iodide N, N-dimethyl-3-pyrrolidinium phenyltrimethoxysilane, N, N-diethyl-3-pyrrolidinium phenyltrimethoxysilane chloride, bromide N, N-diethyl-3-pyrrolidinium phenyltrimethoxysilane, iodide N, N-diethyl-3-pi Lizinium phenyltrimethoxysilane, N, N-ethylmethyl-3-pyrrolidinium phenyltrimethoxysilane chloride, N, N-ethylmethyl-3-pyrrolidinium phenyltrimethoxysilane bromide, N, N-iodide Ethylmethyl-3-pyrrolidinium phenyltrimethoxysilane, N, N-dimethyl-2-piperidinium phenyltrimethoxysilane chloride, N, N-dimethyl-2-piperidinium phenyltrimethoxysilane bromide, iodide N, N-dimethyl-2-piperidinium phenyltrimethoxysilane, N, N-diethyl-2-piperidinium phenyltrimethoxysilane chloride, N, N-diethyl-2-piperidinium phenyltrimethoxysilane bromide N, N-diethyl-2-piperidinium phenyltrimethoxysila iodide N, N-ethylmethyl-2-piperidinium phenyltrimethoxysilane chloride, N, N-ethylmethyl-2-piperidinium phenyltrimethoxysilane bromide, N, N-ethylmethyl-2-pidium iodide Peridinium phenyltrimethoxysilane, N, N-dimethyl-3-piperidinium phenyltrimethoxysilane chloride, N, N-dimethyl-3-piperidinium phenyltrimethoxysilane bromide, N, N-dimethyl iodide 3-piperidinium phenyltrimethoxysilane,
N, N-diethyl-3-piperidinium phenyltrimethoxysilane chloride, N, N-diethyl-3-piperidinium phenyltrimethoxysilane bromide, N, N-diethyl-3-piperidinium phenyltriiodide Methoxysilane, N, N-ethylmethyl-3-piperidinium phenyltrimethoxysilane chloride, N, N-ethylmethyl-3-piperidinium phenyltrimethoxysilane bromide, N, N-ethylmethyl-3 iodide -Piperidinium phenyltrimethoxysilane, N, N-dimethyl-4-piperidinium phenyltrimethoxysilane chloride, N, N-dimethyl-4-piperidinium phenyltrimethoxysilane bromide, N, N-iodide Dimethyl-4-piperidinium phenyltrimethoxysilane, N, N-diethyl-4-piperidinyl chloride Muphenyltrimethoxysilane, N, N-diethyl-4-piperidinium phenyltrimethoxysilane bromide, N, N-diethyl-4-piperidinium phenyltrimethoxysilane iodide, N, N-ethylmethyl chloride 4-piperidinium phenyltrimethoxysilane, N, N-ethylmethyl bromide-4-piperidinium phenyltrimethoxysilane, N, N-ethylmethyl-4-piperidinium phenyltrimethoxysilane iodide, N chloride N, N-dimethyl-2-pyrrolinium phenyltrimethoxysilane, N, N-dimethyl-2-pyrrolinium phenyltrimethoxysilane bromide, N, N-dimethyl-2-pyrrolium phenyltrimethoxysilane iodide, N chloride , N-diethyl-2-pyrroliniumphenyltrimethoxysilane, N, N-bromide Ethyl-2-pyrrolinium phenyltrimethoxysilane, N, N-diethyl-2-pyrroliumphenyltrimethoxysilane iodide, N, N-ethylmethyl-2-pyrroliumphenyltrimethoxysilane chloride, N, N bromide -Ethylmethyl-2-pyrroliniumphenyltrimethoxysilane, N, N-ethylmethyl-2-pyrroliniumphenyltrimethoxysilane iodide, N, N-dimethyl-3-pyrroliumphenyltrimethoxysilane chloride, N-bromide , N-dimethyl-3-pyrrolinium phenyltrimethoxysilane, N, N-dimethyl-3-pyrroliumphenyltrimethoxysilane iodide, N, N-diethyl-3-pyrroliumphenyltrimethoxysilane chloride, N-bromide , N-diethyl-3-pyrroliumphenyltrimethoxysilane, N, N-diethyl-3-pyrrolium phenyltrimethoxysilane, N, N-ethylmethyl-3-pyrroliumphenyltrimethoxysilane chloride, N, N-ethylmethyl-3-pyrroliumphenyltrimethoxy bromide Silane, N, N-ethylmethyl-3-pyrrolinium phenyltrimethoxysilane iodide, N, N-dimethyl-2-pyrrolidinium benzyltrimethoxysilane chloride, N, N-dimethyl-2-pyrrolidinium bromide Benzyltrimethoxysilane, N, N-dimethyl-2-pyrrolidinium iodide benzyltrimethoxysilane, N, N-diethyl-2-pyrrolidinium benzyltrimethoxysilane chloride, N, N-diethyl-2-bromide Pyrrolidinium benzyltrimethoxysilane, N, N-diethyl-2-pyrrolidinium benzene iodide Rutrimethoxysilane, N, N-ethylmethyl-2-pyrrolidinium benzyltrimethoxysilane chloride, N, N-ethylmethyl-2-pyrrolidinium benzyltrimethoxysilane bromide, N, N-ethylmethyl iodide 2-pyrrolidinium benzyltrimethoxysilane, N, N-dimethyl-3-pyrrolidinium benzyltrimethoxysilane chloride, N, N-dimethyl-3-pyrrolidinium benzyltrimethoxysilane bromide, N, N iodide -Dimethyl-3-pyrrolidinium benzyltrimethoxysilane, N, N-diethyl-3-pyrrolidinium benzyltrimethoxysilane chloride, N, N-diethyl-3-pyrrolidinium benzyltrimethoxysilane bromide, iodide N, N-diethyl-3-pyrrolidinium benzyltrimethoxysilane, N, N-chloride Tilmethyl-3-pyrrolidinium benzyltrimethoxysilane, N, N-ethylmethyl-3-pyrrolidinium benzyltrimethoxysilane bromide, N, N-ethylmethyl-3-pyrrolidinium benzyltrimethoxysilane iodide, N, N-dimethyl-2-piperidinium benzyltrimethoxysilane chloride, N, N-dimethyl-2-piperidinium benzyltrimethoxysilane bromide, N, N-dimethyl-2-piperidinium benzyltriiodide Methoxysilane, N, N-diethyl-2-piperidinium benzyltrimethoxysilane chloride, N, N-diethyl-2-piperidinium benzyltrimethoxysilane bromide, iodide N, N-diethyl-2-piperidi Nitrobenzyltrimethoxysilane, N, N-ethylmethyl-2-piperidinium chloride Rutrimethoxysilane, N, N-ethylmethyl-2-piperidinium benzyltrimethoxysilane bromide, N, N-ethylmethyl-2-piperidinium benzyltrimethoxysilane iodide, N, N-dimethyl-3 chloride -Piperidinium benzyltrimethoxysilane, N, N-dimethyl-3-piperidinium benzyltrimethoxysilane bromide, N, N-dimethyl-3-piperidinium benzyltrimethoxysilane iodide, N, N- chloride Diethyl-3-piperidinium benzyltrimethoxysilane, N, N-diethyl-3-piperidinium benzyltrimethoxysilane bromide, N, N-diethyl-3-piperidinium benzyltrimethoxysilane iodide, N chloride , N-ethylmethyl-3-piperidinium benzyltrimethoxysilane, N, N-benzene bromide Rumethyl-3-piperidinium benzyltrimethoxysilane, N, N-ethylmethyl-3-piperidinium benzyltrimethoxysilane iodide, N, N-dimethyl-4-piperidinium benzyltrimethoxysilane chloride, bromide N, N-dimethyl-4-piperidinium benzyltrimethoxysilane, iodide N, N-dimethyl-4-piperidinium benzyltrimethoxysilane, N, N-diethyl-4-piperidinium benzyltrimethoxysilane chloride N, N-diethyl-4-piperidinium benzyltrimethoxysilane bromide, N, N-diethyl-4-piperidinium benzyltrimethoxysilane iodide, N, N-ethylmethyl-4-piperidinium chloride Benzyltrimethoxysilane, N, N-ethylmethyl-4-piperidinium benzyl bromide Trimethoxysilane, N, N-ethylmethyl-4-piperidinium benzyltrimethoxysilane iodide, N, N-dimethyl-2-pyrrolonium benzyltrimethoxysilane chloride, N, N-dimethyl-2-pyrrole bromide Ni-benzyltrimethoxysilane, N, N-dimethyl-2-pyrroliniumbenzyltrimethoxysilane iodide, N, N-diethyl-2-pyrrolinylbenzyltrimethoxysilane chloride, N, N-diethyl-2-pyrrole bromide Ni-benzyltrimethoxysilane, N, N-diethyl-2-pyrroliniumbenzyltrimethoxysilane iodide, N, N-ethylmethyl-2-pyrroliumbenzyltrimethoxysilane chloride, N, N-ethylmethyl-2 bromide -Pyrrolium benzyltrimethoxysilane, iodide N, N-ethylmethyl-2- Pyrrolium benzyltrimethoxysilane, N, N-dimethyl-3-pyrroliumbenzyltrimethoxysilane chloride, N, N-dimethyl-3-pyrroliumbenzyltrimethoxysilane bromide, N, N-dimethyl-3-iodide Pyrrolium benzyltrimethoxysilane, N, N-diethyl-3-pyrroliumbenzyltrimethoxysilane chloride, N, N-diethyl-3-pyrroliumbenzyltrimethoxysilane bromide, N, N-diethyl-3-iodide Pyrrolium benzyltrimethoxysilane, N, N-ethylmethyl-3-pyrroliumbenzyltrimethoxysilane chloride, N, N-ethylmethyl-3-pyrroliumbenzyltrimethoxysilane bromide, N, N-ethylmethyl iodide -3-pyrrolinylbenzyltrimethoxysilane, etc. It is not necessarily limited to the silicon-containing compounds exemplified here, and Y in general formula (3) may be a group derived from a heterocyclic non-aromatic quaternary ammonium ion represented by general formula (14). It does not matter. The alkyl groups such as propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group and the like exemplified here are not limited to linear n-forms, but are isoforms, sec-forms, tert-forms. It may be branched or cyclic like a body.

Specific examples of the silicon-containing compound in the case where Y in the general formula (3) is a group derived from a heterocyclic aromatic quaternary ammonium ion represented by the general formula (15) include, for example, N-methyl fluoride. 2-pyridinium trimethoxysilane, N-methyl-2-pyridinium trimethoxysilane chloride, N-methyl-2-pyridinium trimethoxysilane bromide, N-methyl-2-pyridinium trimethoxysilane iodide, N-methyl fluoride 2-pyridinium triethoxysilane, N-methyl-2-pyridinium triethoxysilane chloride, N-methyl-2-pyridinium triethoxysilane bromide, N-methyl-2-pyridinium triethoxysilane iodide, N-fluoride Methyl-2-pyridinium tripropoxysilane, N-methyl-2-pyridinium chloride triprochloride Xisilane, N-methyl-2-pyridinium tripropoxysilane bromide, N-methyl-2-pyridinium tripropoxysilane iodide, N-methyl-2-pyridinium trichlorosilane fluoride, N-methyl-2-pyridinium trichlorosilane chloride N-methyl-2-pyridinium trichlorosilane bromide, N-methyl-2-pyridinium trichlorosilane iodide, N-methyl-2-pyridinium tribromosilane fluoride, N-methyl-2-pyridinium tribromosilane chloride, N-methyl-2-pyridinium tribromosilane bromide, N-methyl-2-pyridinium tribromosilane iodide, N-methyl-2-pyridinium triiodosilane fluoride, N-methyl-2-pyridinium triiodosilane chloride N-methyl-2-pyridinium bromide Liiodosilane, N-methyl-2-pyridinium triiodosilane iodide, N-methyl-2-pyridinium methyltrimethoxysilane chloride, N-methyl-2-pyridinium methyltrimethoxysilane bromide, N-methyl-2-iodide Pyridinium methyltrimethoxysilane, N-methyl-2-pyridinium ethyltrimethoxysilane chloride, N-methyl-2-pyridinium ethyltrimethoxysilane bromide, N-methyl-2-pyridinium ethyltrimethoxysilane iodide, N-chloride Methyl-2-pyridiniumpropyltrimethoxysilane, N-methyl-2-pyridiniumpropyltrimethoxysilane bromide, N-methyl-2-pyridiniumpropyltrimethoxysilane iodide, N-methyl-2-pyridiniumbutyltrimethoxysilane chloride , N bromide -Methyl-2-pyridinium butyltrimethoxysilane, N-methyl-2-pyridinium butyltrimethoxysilane iodide, N-methyl-2-pyridinium pentyltrimethoxysilane chloride, N-methyl-2-pyridinium pentyltrimethoxy bromide Silane, N-methyl-2-pyridinium pentyltrimethoxysilane iodide, N-methyl-2-pyridinium hexyltrimethoxysilane chloride, N-methyl-2-pyridinium hexyltrimethoxysilane bromide, N-methyl-2 iodide -Pyridinium hexyltrimethoxysilane, N-methyl-2-pyridinium heptyltrimethoxysilane chloride, N-methyl-2-pyridinium heptyltrimethoxysilane bromide, N-methyl-2-pyridinium heptyltrimethoxysilane iodide, N chloride − Til-2-pyridinium octyltrimethoxysilane, N-methyl-2-pyridinium octyltrimethoxysilane bromide, N-methyl-2-pyridinium octyltrimethoxysilane iodide, N-ethyl-2-pyridinium trimethoxysilane chloride, N-ethyl-2-pyridinium trimethoxysilane bromide, N-ethyl-2-pyridinium trimethoxysilane iodide, N-ethyl-2-pyridinium methyltrimethoxysilane chloride, N-ethyl-2-pyridinium methyltribromide Methoxysilane, N-ethyl-2-pyridinium methyltrimethoxysilane iodide, N-ethyl-2-pyridinium ethyltrimethoxysilane chloride, N-ethyl-2-pyridiniumethyltrimethoxysilane bromide, N-ethyl iodide 2-pyridinium ethyl Methoxysilane, N-ethyl-2-pyridiniumpropyltrimethoxysilane chloride, N-ethyl-2-pyridiniumpropyltrimethoxysilane bromide, N-ethyl-2-pyridiniumpropyltrimethoxysilane iodide, N-ethyl-2 chloride -Pyridinium butyltrimethoxysilane, N-ethyl-2-pyridinium butyltrimethoxysilane bromide, N-ethyl-2-pyridinium butyltrimethoxysilane iodide, N-propyl-2-pyridinium trimethoxysilane chloride, N bromide -Propyl-2-pyridinium trimethoxysilane, N-propyl-2-pyridinium trimethoxysilane iodide, N-propyl-2-pyridinium methyltrimethoxysilane chloride, N-propyl-2-pyridinium methyltrimethoxysilane bromide, Iodide N -Propyl-2-pyridinium methyltrimethoxysilane, N-propyl-2-pyridinium ethyltrimethoxysilane chloride, N-propyl-2-pyridinium ethyltrimethoxysilane bromide, N-propyl-2-pyridinium ethyltrimethoxy iodide Silane, N-propyl-2-pyridiniumpropyltrimethoxysilane chloride, N-propyl-2-pyridiniumpropyltrimethoxysilane bromide, N-propyl-2-pyridiniumpropyltrimethoxysilane iodide, N-propyl-2-chloride Pyridinium butyltrimethoxysilane, N-propyl-2-pyridiniumbutyltrimethoxysilane bromide, N-propyl-2-pyridiniumbutyltrimethoxysilane iodide, N-butyl-2-pyridiniumtrimethoxysilane chloride, N-bromide Tyl-2-pyridinium trimethoxysilane, N-butyl-2-pyridinium trimethoxysilane iodide, N-butyl-2-pyridinium methyltrimethoxysilane chloride, N-butyl-2-pyridinium methyltrimethoxysilane bromide, iodine N-butyl-2-pyridinium methyltrimethoxysilane, N-butyl-2-pyridiniumethyltrimethoxysilane chloride, N-butyl-2-pyridiniumethyltrimethoxysilane bromide, N-butyl-2-pyridiniumethyl iodide Trimethoxysilane, N-butyl-2-pyridiniumpropyltrimethoxysilane chloride, N-butyl-2-pyridiniumpropyltrimethoxysilane bromide, N-butyl-2-pyridiniumpropyltrimethoxysilane iodide, N-butyl chloride 2-pyridinium bu Rutrimethoxysilane, N-butyl-2-pyridinium butyltrimethoxysilane bromide, N-butyl-2-pyridinium butyltrimethoxysilane iodide, N-pentyl-2-pyridinium trimethoxysilane chloride, N-pentyl bromide 2-pyridinium trimethoxysilane, N-pentyl-2-pyridinium trimethoxysilane iodide, N-pentyl-2-pyridinium methyltrimethoxysilane chloride, N-pentyl-2-pyridinium methyltrimethoxysilane bromide, N iodide -Pentyl-2-pyridinium methyltrimethoxysilane, N-pentyl-2-pyridiniumethyltrimethoxysilane chloride, N-pentyl-2-pyridiniumethyltrimethoxysilane bromide, N-pentyl-2-pyridiniumethyltrimethoxy iodide Silane N-pentyl-2-pyridiniumpropyltrimethoxysilane chloride, N-pentyl-2-pyridiniumpropyltrimethoxysilane bromide, N-pentyl-2-pyridiniumpropyltrimethoxysilane iodide, N-pentyl-2-pyridinium chloride Butyltrimethoxysilane, N-pentyl-2-pyridiniumbutyltrimethoxysilane bromide, N-pentyl-2-pyridiniumbutyltrimethoxysilane iodide, N-hexyl-2-pyridiniumtrimethoxysilane chloride, N-hexyl bromide -2-pyridinium trimethoxysilane, N-hexyl-2-pyridinium trimethoxysilane iodide, N-hexyl-2-pyridinium methyltrimethoxysilane chloride, N-hexyl-2-pyridinium methyltrimethoxysilane bromide, iodide N- Xyl-2-pyridinium methyltrimethoxysilane, N-hexyl-2-pyridiniumethyltrimethoxysilane chloride, N-hexyl-2-pyridiniumethyltrimethoxysilane bromide, N-hexyl-2-pyridiniumethyltrimethoxysilane iodide N-hexyl-2-pyridiniumpropyltrimethoxysilane chloride, N-hexyl-2-pyridiniumpropyltrimethoxysilane bromide, N-hexyl-2-pyridiniumpropyltrimethoxysilane iodide, N-hexyl-2-pyridinium chloride Butyltrimethoxysilane, N-hexyl-2-pyridiniumbutyltrimethoxysilane bromide, N-hexyl-2-pyridiniumbutyltrimethoxysilane iodide, N-heptyl-2-pyridiniumtrimethoxysilane chloride, N-bromide Ptyl-2-pyridinium trimethoxysilane, N-heptyl-2-pyridinium trimethoxysilane iodide, N-heptyl-2-pyridinium methyltrimethoxysilane chloride, N-heptyl-2-pyridinium methyltrimethoxysilane bromide, iodine N-heptyl-2-pyridinium methyltrimethoxysilane, N-heptyl-2-pyridiniumethyltrimethoxysilane chloride, N-heptyl-2-pyridiniumethyltrimethoxysilane bromide, N-heptyl-2-pyridiniumethyl iodide Trimethoxysilane, N-heptyl-2-pyridiniumpropyltrimethoxysilane chloride, N-heptyl-2-pyridiniumpropyltrimethoxysilane bromide, N-heptyl-2-pyridiniumpropyltrimethoxysilane iodide, N-heptyl chloride Ru-2-pyridinium butyltrimethoxysilane, N-heptyl-2-pyridiniumbutyltrimethoxysilane bromide, N-heptyl-2-pyridiniumbutyltrimethoxysilane iodide, N-octyl-2-pyridiniumtrimethoxysilane chloride, N-octyl-2-pyridinium trimethoxysilane bromide, N-octyl-2-pyridinium trimethoxysilane iodide, N-octyl-2-pyridinium methyltrimethoxysilane chloride, N-octyl-2-pyridinium methyltribromide Methoxysilane, N-octyl-2-pyridinium methyltrimethoxysilane iodide, N-octyl-2-pyridiniumethyltrimethoxysilane chloride, N-octyl-2-pyridiniumethyltrimethoxysilane bromide, N-octyl iodide 2-pyridini Methyltrimethoxysilane, N-octyl-2-pyridiniumpropyltrimethoxysilane chloride, N-octyl-2-pyridiniumpropyltrimethoxysilane bromide, N-octyl-2-pyridiniumpropyltrimethoxysilane iodide, N-chloride Octyl-2-pyridinium butyltrimethoxysilane, N-octyl-2-pyridiniumbutyltrimethoxysilane bromide, N-octyl-2-pyridiniumbutyltrimethoxysilane iodide, N-methyl-3-pyridiniumtrimethoxysilane chloride, N-methyl-3-pyridinium trimethoxysilane bromide, N-methyl-3-pyridinium trimethoxysilane iodide, N-methyl-3-pyridinium methyltrimethoxysilane chloride, N-methyl-3-pyridinium methyltribromide Methoxy Orchid, N-methyl-3-pyridinium methyltrimethoxysilane iodide, N-methyl-3-pyridiniumethyltrimethoxysilane chloride, N-methyl-3-pyridiniumethyltrimethoxysilane bromide, N-methyl-3 iodide -Pyridinium ethyltrimethoxysilane, N-methyl-3-pyridiniumpropyltrimethoxysilane chloride, N-methyl-3-pyridiniumpropyltrimethoxysilane bromide, N-methyl-3-pyridiniumpropyltrimethoxysilane iodide,
N-methyl-3-pyridinium butyltrimethoxysilane chloride, N-methyl-3-pyridiniumbutyltrimethoxysilane bromide, N-methyl-3-pyridiniumbutyltrimethoxysilane iodide, N-ethyl-3-pyridinium chloride Methoxysilane, N-ethyl-3-pyridinium trimethoxysilane bromide, N-ethyl-3-pyridinium trimethoxysilane iodide, N-ethyl-3-pyridinium methyltrimethoxysilane chloride, N-ethyl-3-bromide Pyridinium methyltrimethoxysilane, N-ethyl-3-pyridiniummethyltrimethoxysilane iodide, N-ethyl-3-pyridiniumethyltrimethoxysilane chloride, N-ethyl-3-pyridiniumethyltrimethoxysilane bromide, N iodide -Ethyl-3-pyridinium ethyl Limethoxysilane, N-ethyl-3-pyridiniumpropyltrimethoxysilane chloride, N-ethyl-3-pyridiniumpropyltrimethoxysilane bromide, N-ethyl-3-pyridiniumpropyltrimethoxysilane iodide, N-ethyl chloride 3-pyridinium butyltrimethoxysilane, N-ethyl-3-pyridiniumbutyltrimethoxysilane bromide, N-ethyl-3-pyridiniumbutyltrimethoxysilane iodide, N-propyl-3-pyridiniumtrimethoxysilane chloride, bromide N-propyl-3-pyridinium trimethoxysilane, N-propyl-3-pyridinium trimethoxysilane iodide, N-propyl-3-pyridinium methyltrimethoxysilane chloride, N-propyl-3-pyridinium methyltrimethoxysilane bromide , You N-propyl-3-pyridinium methyltrimethoxysilane, N-propyl-3-pyridiniumethyltrimethoxysilane chloride, N-propyl-3-pyridiniumethyltrimethoxysilane bromide, N-propyl-3-pyridiniumethyltriiodide iodide Methoxysilane, N-propyl-3-pyridiniumpropyltrimethoxysilane chloride, N-propyl-3-pyridiniumpropyltrimethoxysilane bromide, N-propyl-3-pyridiniumpropyltrimethoxysilane iodide, N-propyl-3 chloride -Pyridinium butyltrimethoxysilane, N-propyl-3-pyridiniumbutyltrimethoxysilane bromide, N-propyl-3-pyridiniumbutyltrimethoxysilane iodide, N-butyl-3-pyridiniumtrimethoxysilane chloride, N-bromide -Butyl-3-pyridinium trimethoxysilane, N-butyl-3-pyridinium trimethoxysilane iodide, N-butyl-3-pyridinium methyltrimethoxysilane chloride, N-butyl-3-pyridiniummethyltrimethoxysilane bromide, N-butyl-3-pyridinium methyltrimethoxysilane iodide, N-butyl-3-pyridiniumethyltrimethoxysilane chloride, N-butyl-3-pyridiniumethyltrimethoxysilane bromide, N-butyl-3-pyridinium iodide Ethyltrimethoxysilane, N-butyl-3-pyridiniumpropyltrimethoxysilane chloride, N-butyl-3-pyridiniumpropyltrimethoxysilane bromide, N-butyl-3-pyridiniumpropyltrimethoxysilane iodide, N-butyl chloride -3-pyridinium Tiltrimethoxysilane, N-butyl-3-pyridiniumbutyltrimethoxysilane bromide, N-butyl-3-pyridiniumbutyltrimethoxysilane iodide, N-methyl-4-pyridiniumtrimethoxysilane chloride, N-methyl bromide -4-pyridinium trimethoxysilane, N-methyl-4-pyridinium trimethoxysilane iodide, N-methyl-4-pyridinium methyltrimethoxysilane chloride, N-methyl-4-pyridinium methyltrimethoxysilane bromide, iodide N-methyl-4-pyridinium methyltrimethoxysilane, N-methyl-4-pyridiniumethyltrimethoxysilane chloride, N-methyl-4-pyridiniumethyltrimethoxysilane bromide, N-methyl-4-pyridiniumethyltriiodide iodide Methoxysilane, N-methyl chloride -4-pyridiniumpropyltrimethoxysilane, N-methyl-4-pyridiniumpropyltrimethoxysilane bromide, N-methyl-4-pyridiniumpropyltrimethoxysilane iodide, N-methyl-4-pyridiniumbutyltrimethoxysilane chloride, N-methyl-4-pyridinium butyltrimethoxysilane bromide, N-methyl-4-pyridinium butyltrimethoxysilane iodide, N-ethyl-4-pyridinium trimethoxysilane chloride, N-ethyl-4-pyridinium tribromide Methoxysilane, N-ethyl-4-pyridinium trimethoxysilane iodide, N-ethyl-4-pyridinium methyltrimethoxysilane chloride, N-ethyl-4-pyridiniummethyltrimethoxysilane bromide, N-ethyl-4 iodide -Pyridinium methyltrimeth Xisilane, N-ethyl-4-pyridinium ethyltrimethoxysilane chloride, N-ethyl-4-pyridiniumethyltrimethoxysilane bromide, N-ethyl-4-pyridinium ethyltrimethoxysilane iodide, N-ethyl-4-chloride Pyridiniumpropyltrimethoxysilane, N-ethyl-4-pyridiniumpropyltrimethoxysilane bromide, N-ethyl-4-pyridiniumpropyltrimethoxysilane iodide, N-ethyl-4-pyridiniumbutyltrimethoxysilane chloride, N-bromide -Ethyl-4-pyridinium butyltrimethoxysilane, N-ethyl-4-pyridiniumbutyltrimethoxysilane iodide, N-propyl-4-pyridiniumtrimethoxysilane chloride, N-propyl-4-pyridiniumtrimethoxysilane bromide, N-iodide Pyr-4-pyridinium trimethoxysilane, N-propyl-4-pyridiniummethyltrimethoxysilane chloride, N-propyl-4-pyridiniummethyltrimethoxysilane bromide, N-propyl-4-pyridiniummethyltrimethoxysilane iodide, N-propyl-4-pyridinium ethyltrimethoxysilane chloride, N-propyl-4-pyridiniumethyltrimethoxysilane bromide, N-propyl-4-pyridiniumethyltrimethoxysilane iodide, N-propyl-4-pyridiniumpropyl chloride Trimethoxysilane, N-propyl-4-pyridiniumpropyltrimethoxysilane bromide, N-propyl-4-pyridiniumpropyltrimethoxysilane iodide, N-propyl-4-pyridiniumbutyltrimethoxysilane chloride, N-propyl bromide Pyr-4-pyridinium butyltrimethoxysilane, N-propyl-4-pyridiniumbutyltrimethoxysilane iodide, N-butyl-4-pyridiniumtrimethoxysilane chloride, N-butyl-4-pyridiniumtrimethoxysilane bromide, iodine N-butyl-4-pyridinium trimethoxysilane, N-butyl-4-pyridiniummethyltrimethoxysilane chloride, N-butyl-4-pyridiniummethyltrimethoxysilane bromide, N-butyl-4-pyridiniummethyltriiodide Methoxysilane, N-butyl-4-pyridiniumethyltrimethoxysilane chloride, N-butyl-4-pyridiniumethyltrimethoxysilane bromide, N-butyl-4-pyridiniumethyltrimethoxysilane iodide, N-butyl-4 chloride -Pyridinium propyltrime Toxisilane, N-butyl-4-pyridiniumpropyltrimethoxysilane bromide, N-butyl-4-pyridiniumpropyltrimethoxysilane iodide, N-butyl-4-pyridiniumbutyltrimethoxysilane chloride, N-butyl-4 bromide -Pyridinium butyltrimethoxysilane, N-butyl-4-pyridiniumbutyltrimethoxysilane iodide, N-methyl-2-quinolinium trimethoxysilane chloride, N-methyl-2-quinolinium trimethoxysilane bromide, N-methyl-2-quinolinium trimethoxysilane iodide, N-methyl-2-quinolinium methyltrimethoxysilane chloride, N-methyl-2-quinolinium methyltrimethoxysilane bromide, N-iodide Methyl-2-quinolinium methyltrimethoxysilane, N-methyl-2-chloride Norinium ethyltrimethoxysilane, N-methyl-2-quinolinium ethyltrimethoxysilane bromide, N-methyl-2-quinolinium ethyltrimethoxysilane iodide, N-ethyl-2-quinolinium chloride Methoxysilane, N-ethyl-2-quinolinium trimethoxysilane bromide, N-ethyl-2-quinolinium trimethoxysilane iodide, N-ethyl-2-quinolinium methyltrimethoxysilane chloride, bromide N-ethyl-2-quinolinium methyltrimethoxysilane, N-ethyl-2-quinolinium methyltrimethoxysilane iodide, N-ethyl-2-quinolinium ethyltrimethoxysilane chloride, N-ethyl bromide 2-quinolinium ethyltrimethoxysilane, N-ethyl-2-quinolinium ethyltrimethoxysilane iodide, N-methyl-3-quinolinium trimethoxysilane, N-methyl-3-quinolinium trimethoxysilane bromide, N-methyl-3-quinolinium trimethoxysilane iodide, N-methyl-3 chloride -Quinolinium methyltrimethoxysilane, N-methyl-3-quinolinium methyltrimethoxysilane bromide, N-methyl-3-quinolinium methyltrimethoxysilane iodide, N-methyl-3-quinori chloride N-ethyltrimethoxysilane, N-methyl-3-quinolinium ethyltrimethoxysilane bromide, N-methyl-3-quinolinium ethyltrimethoxysilane iodide, N-ethyl-3-quinolinium trimethoxy chloride Silane, N-ethyl-3-quinolinium trimethoxysilane bromide, N-ethyl-3-quinolinium trimethoxysilane iodide,
N-ethyl-3-quinolinium methyltrimethoxysilane chloride, N-ethyl-3-quinolinium methyltrimethoxysilane bromide, N-ethyl-3-quinolinium methyltrimethoxysilane iodide, N-chloride Ethyl-3-quinolinium ethyltrimethoxysilane, N-ethyl-3-quinolinium ethyltrimethoxysilane bromide, N-ethyl-3-quinolinium ethyltrimethoxysilane iodide, N-methyl-4 chloride -Quinolinium trimethoxysilane, N-methyl-4-quinolinium trimethoxysilane bromide, N-methyl-4-quinolinium trimethoxysilane iodide, N-methyl-4-quinolinium methyltrichloride Methoxysilane, N-methyl-4-quinolinium methyltrimethoxysilane bromide, N-methyl-4-quinolinium methyl iodide Limethoxysilane, N-methyl-4-quinolinium ethyltrimethoxysilane chloride, N-methyl-4-quinolinium ethyltrimethoxysilane bromide, N-methyl-4-quinolinium ethyltrimethoxysilane iodide N-ethyl-4-quinolinium trimethoxysilane chloride, N-ethyl-4-quinolinium trimethoxysilane bromide, N-ethyl-4-quinolinium trimethoxysilane iodide, N-ethyl chloride 4-quinolinium methyltrimethoxysilane, N-ethyl-4-quinolinium methyltrimethoxysilane bromide, N-ethyl-4-quinolinium methyltrimethoxysilane iodide, N-ethyl-4-ki chloride Norinium ethyltrimethoxysilane, N-ethyl-4-quinolinium ethyltrimethoxysilane bromide, N-ethyl-4 iodide Quinolinium ethyltrimethoxysilane, N-methyl-5-quinolinium trimethoxysilane chloride, N-methyl-5-quinolinium trimethoxysilane bromide, N-methyl-5-quinolinium trimethoxy iodide Silane, N-methyl-5-quinolinium methyltrimethoxysilane chloride, N-methyl-5-quinolinium methyltrimethoxysilane bromide, N-methyl-5-quinolinium methyltrimethoxysilane iodide, chloride N-methyl-5-quinolinium ethyltrimethoxysilane, N-methyl-5-quinolinium ethyltrimethoxysilane bromide, N-methyl-5-quinolinium ethyltrimethoxysilane iodide, N-ethyl chloride -5-quinolinium trimethoxysilane, N-ethyl-5-quinolinium trimethoxysilane, N-ethyl iodide Ru-5-quinolinium trimethoxysilane, N-ethyl-5-quinolinium methyltrimethoxysilane chloride, N-ethyl-5-quinolinium methyltrimethoxysilane bromide, N-ethyl-5-iodide Quinolinium methyltrimethoxysilane, N-ethyl-5-quinolinium ethyltrimethoxysilane, N-ethyl-5-quinolinium ethyltrimethoxysilane bromide, N-ethyl-5-quinolinium iodide Ethyltrimethoxysilane, N-methyl-6-quinolinium trimethoxysilane chloride, N-methyl-6-quinolinium trimethoxysilane bromide, N-methyl-6-quinolinium trimethoxysilane iodide, chloride N-methyl-6-quinolinium methyltrimethoxysilane, N-methyl-6-quinolinium methyltrimethoxysilane bromide, N-methyl-6-quinolinium methyltrimethoxysilane, N-methyl-6-quinolinium ethyltrimethoxysilane chloride, N-methyl-6-quinoliniumethyltrimethoxysilane bromide, N-iodide -Methyl-6-quinolinium ethyltrimethoxysilane, N-ethyl-6-quinolinium trimethoxysilane chloride, N-ethyl-6-quinolinium trimethoxysilane bromide, N-ethyl-6-iodide Quinolinium trimethoxysilane, N-ethyl-6-quinolinium methyltrimethoxysilane chloride, N-ethyl-6-quinoliniummethyltrimethoxysilane bromide, N-ethyl-6-quinolinium methyl iodide Trimethoxysilane, N-ethyl-6-quinolinium ethyl chloride trimethoxysilane, N-ethyl-6-quinolinium ethyl bromide Limethoxysilane, N-ethyl-6-quinolinium ethyltrimethoxysilane iodide, N-methyl-7-quinolinium trimethoxysilane chloride, N-methyl-7-quinolinium trimethoxysilane bromide, iodine N-methyl-7-quinolinium trimethoxysilane, N-methyl-7-quinolinium methyltrimethoxysilane, N-methyl-7-quinolinium methyltrimethoxysilane bromide, N-methyl iodide -7-quinolinium methyltrimethoxysilane, N-methyl-7-quinoliniumethyltrimethoxysilane chloride, N-methyl-7-quinoliniumethyltrimethoxysilane bromide, N-methyl-7-iodide Quinolinium ethyltrimethoxysilane, N-ethyl-7-quinolinium trimethoxysilane chloride, N-ethyl-7-quinori bromide Nitrimethoxysilane, N-ethyl-7-quinolinium trimethoxysilane iodide, N-ethyl-7-quinolinium methyltrimethoxysilane chloride, N-ethyl-7-quinolinium methyltrimethoxysilane bromide N-ethyl-7-quinolinium methyltrimethoxysilane iodide, N-ethyl-7-quinolinium ethyltrimethoxysilane chloride, N-ethyl-7-quinolinium ethyltrimethoxysilane bromide, iodide N-ethyl-7-quinolinium ethyltrimethoxysilane, N-methyl-8-quinolinium trimethoxysilane, N-methyl-8-quinolinium trimethoxysilane bromide, N-methyl-8 iodide -Quinolinium trimethoxysilane, N-methyl-8-quinolinium methyltrimethoxysilane chloride, N-methyl-8 bromide Quinolinium methyltrimethoxysilane, N-methyl-8-quinoliniummethyltrimethoxysilane iodide, N-methyl-8-quinoliniumethyltrimethoxysilane chloride, N-methyl-8-quinolinium bromide Ethyltrimethoxysilane, N-methyl-8-quinolinium ethyltrimethoxysilane iodide, N-ethyl-8-quinoliniumtrimethoxysilane chloride, N-ethyl-8-quinoliniumtrimethoxysilane bromide, N-ethyl-8-quinolinium trimethoxysilane iodide, N-ethyl-8-quinolinium methyltrimethoxysilane chloride, N-ethyl-8-quinolinium methyltrimethoxysilane bromide, N-iodide iodide Ethyl-8-quinolinium methyltrimethoxysilane, N-ethyl-8-quinolinium ethyltrimethoxysilane chloride N-ethyl-8-quinolinium ethyltrimethoxysilane bromide, N-ethyl-8-quinolinium ethyltrimethoxysilane iodide, N-methyl-1-isoquinolinium trimethoxysilane chloride, bromide N -Methyl-1-isoquinolinium trimethoxysilane, N-methyl-1-isoquinolinium trimethoxysilane iodide, N-methyl-1-isoquinolinium methyltrimethoxysilane chloride, N-methyl bromide -1-Isoquinolinium methyltrimethoxysilane, N-methyl-1-isoquinolinium methyltrimethoxysilane iodide, N-methyl-1-isoquinolinium ethyltrimethoxysilane chloride, N-methyl bromide -1-Isoquinolinium ethyltrimethoxysilane, N-methyl-1-isoquinolinium ethyltrimethoxysilane, salt N-ethyl-1-isoquinolinium trimethoxysilane, N-ethyl-1-isoquinolinium trimethoxysilane bromide, N-ethyl-1-isoquinolinium trimethoxysilane iodide, N-chloride Ethyl-1-isoquinolinium methyltrimethoxysilane, N-ethyl-1-isoquinolinium methyltrimethoxysilane bromide, N-ethyl-1-isoquinolinium methyltrimethoxysilane iodide, N-chloride Ethyl-1-isoquinolinium ethyltrimethoxysilane, N-ethyl-1-isoquinolinium ethyltrimethoxysilane bromide, N-ethyl-1-isoquinolinium ethyltrimethoxysilane iodide, N-chloride Methyl-3-isoquinolinium trimethoxysilane, N-methyl-3-isoquinolinium trimethoxysilane bromide, N-iodide Tyl-3-isoquinolinium trimethoxysilane, N-methyl-3-isoquinolinium methyltrimethoxysilane, N-methyl-3-isoquinolinium methyltrimethoxysilane bromide, N-methyl iodide -3-Isoquinolinium methyltrimethoxysilane, N-methyl-3-isoquinolinium ethyltrimethoxysilane, N-methyl-3-isoquinolinium ethyltrimethoxysilane bromide, N-methyl iodide -3-Isoquinolinium ethyltrimethoxysilane, N-ethyl-3-isoquinolinium trimethoxysilane chloride, N-ethyl-3-isoquinolinium trimethoxysilane bromide, N-ethyl-3 iodide -Isoquinolinium trimethoxysilane, N-ethyl-3-isoquinolinium methyltrimethoxysilane chloride, N-ethyl bromide Ru-3-isoquinolinium methyltrimethoxysilane, iodide N-ethyl-3-isoquinoliniummethyltrimethoxysilane, N-ethyl-3-isoquinolinium ethyltrimethoxysilane chloride, N-bromide Ethyl-3-isoquinolinium ethyltrimethoxysilane, iodide N-ethyl-3-isoquinolinium ethyltrimethoxysilane, N-methyl-4-isoquinolinium trimethoxysilane chloride, N-methyl bromide -4-isoquinolinium trimethoxysilane, iodide N-methyl-4-isoquinolinium trimethoxysilane, N-methyl-4-isoquinolinium methyltrimethoxysilane chloride, N-methyl-4 bromide -Isoquinolinium methyltrimethoxysilane, N-methyl-4-isoquinolinium methyltrimethoxysilane iodide, N chloride -Methyl-4-isoquinolinium ethyltrimethoxysilane, N-methyl-4-isoquinolinium ethyltrimethoxysilane bromide, N-methyl-4-isoquinolinium ethyltrimethoxysilane iodide, N chloride -Ethyl-4-isoquinolinium trimethoxysilane, N-ethyl-4-isoquinolinium trimethoxysilane bromide, N-ethyl-4-isoquinolinium trimethoxysilane iodide, N-ethyl chloride- 4-isoquinolinium methyltrimethoxysilane, N-ethyl-4-isoquinolinium methyltrimethoxysilane bromide, N-ethyl-4-isoquinolinium methyltrimethoxysilane iodide, N-ethyl chloride 4-isoquinolinium ethyltrimethoxysilane, N-ethyl-4-isoquinolinium ethyltrimethoxysilane bromide, N-ethyl-4-isoquinolinium ethyltrimethoxysilane, N-methyl-5-isoquinolinium trimethoxysilane, N-methyl-5-isoquinolinium trimethoxysilane bromide, N iodide -Methyl-5-isoquinolinium trimethoxysilane, N-methyl-5-isoquinolinium methyltrimethoxysilane chloride,
N-methyl-5-isoquinolinium methyltrimethoxysilane bromide, N-methyl-5-isoquinolinium methyltrimethoxysilane iodide, N-methyl-5-isoquinolinium ethyltrimethoxysilane chloride, N-methyl-5-isoquinolinium ethyltrimethoxysilane bromide, N-methyl-5-isoquinolinium ethyltrimethoxysilane iodide, N-ethyl-5-isoquinolinium trimethoxysilane chloride, odor N-ethyl-5-isoquinolinium trimethoxysilane, N-ethyl-5-isoquinolinium trimethoxysilane iodide, N-ethyl-5-isoquinolinium methyltrimethoxysilane chloride, bromide N -Ethyl-5-isoquinolinium methyltrimethoxysilane, N-ethyl-5-isoquinolinium methyltrimethoxysilane iodide N-ethyl-5-isoquinolinium ethyltrimethoxysilane, N-ethyl-5-isoquinolinium ethyltrimethoxysilane bromide, N-ethyl-5-isoquinolinium ethyltrimethoxy iodide Silane, N-methyl-6-isoquinolinium trimethoxysilane chloride, N-methyl-6-isoquinolinium trimethoxysilane bromide, N-methyl-6-isoquinolinium trimethoxysilane iodide, chloride N-methyl-6-isoquinolinium methyltrimethoxysilane, N-methyl-6-isoquinolinium methyltrimethoxysilane bromide, N-methyl-6-isoquinolinium methyltrimethoxysilane iodide, chloride N-methyl-6-isoquinolinium ethyltrimethoxysilane, N-methyl-6-isoquinolinium ethyltrimethoxy bromide Silane, N-methyl-6-isoquinolinium ethyltrimethoxysilane iodide, N-ethyl-6-isoquinolinium trimethoxysilane chloride, N-ethyl-6-isoquinolinium trimethoxysilane bromide, N-ethyl-6-isoquinolinium trimethoxysilane iodide, N-ethyl-6-isoquinolinium methyltrimethoxysilane chloride, N-ethyl-6-isoquinolinium methyltrimethoxysilane bromide, iodine N-ethyl-6-isoquinolinium methyltrimethoxysilane, N-ethyl-6-isoquinolinium ethyltrimethoxysilane chloride, N-ethyl-6-isoquinolinium ethyltrimethoxysilane bromide, iodine N-ethyl-6-isoquinolinium ethyltrimethoxysilane, N-methyl-7-isoquinolinium trimethoxy chloride Silane, N-methyl-7-isoquinolinium trimethoxysilane bromide, N-methyl-7-isoquinolinium trimethoxysilane iodide, N-methyl-7-isoquinolinium methyltrimethoxysilane chloride, N-methyl-7-isoquinolinium methyltrimethoxysilane bromide, N-methyl-7-isoquinolinium methyltrimethoxysilane iodide, N-methyl-7-isoquinolinium ethyltrimethoxysilane chloride, N-methyl-7-isoquinolinium ethyltrimethoxysilane bromide, iodide N-methyl-7-isoquinolinium ethyltrimethoxysilane, N-ethyl-7-isoquinolinium trimethoxysilane chloride, odor N-ethyl-7-isoquinolinium trimethoxysilane, N-ethyl-7-isoquinolinium trimethoxysilane iodide N-ethyl-7-isoquinolinium methyltrimethoxysilane chloride, N-ethyl-7-isoquinolinium methyltrimethoxysilane bromide, N-ethyl-7-isoquinolinium methyltrimethoxysilane iodide, N-ethyl-7-isoquinolinium ethyltrimethoxysilane chloride, N-ethyl-7-isoquinolinium ethyltrimethoxysilane bromide, N-ethyl-7-isoquinolinium ethyltrimethoxysilane iodide, N-methyl-8-isoquinolinium trimethoxysilane chloride, N-methyl-8-isoquinolinium trimethoxysilane bromide, N-methyl-8-isoquinolinium trimethoxysilane iodide, N-chloride Methyl-8-isoquinolinium methyltrimethoxysilane, N-methyl-8-isoquinolinium methyltrimethoxysilane bromide N-methyl-8-isoquinolinium methyltrimethoxysilane, N-methyl-8-isoquinolinium ethyltrimethoxysilane chloride, N-methyl-8-isoquinolinium ethyltrimethoxy bromide Silane, N-methyl-8-isoquinolinium ethyltrimethoxysilane iodide, N-ethyl-8-isoquinolinium trimethoxysilane chloride, N-ethyl-8-isoquinolinium trimethoxysilane bromide, N-ethyl-8-isoquinolinium trimethoxysilane iodide, N-ethyl-8-isoquinolinium methyltrimethoxysilane chloride, N-ethyl-8-isoquinolinium methyltrimethoxysilane bromide, iodine N-ethyl-8-isoquinolinium methyltrimethoxysilane, N-ethyl-8-isoquinolinium ethyltrimethoxy chloride Sisilane, N-ethyl-8-isoquinolinium ethyltrimethoxysilane bromide, N-ethyl-8-isoquinolinium ethyltrimethoxysilane iodide, N-methyl-2-pyridinium phenyltrimethoxysilane chloride, odor N-methyl-2-pyridinium phenyltrimethoxysilane, N-methyl-2-pyridinium phenyltrimethoxysilane iodide, N-ethyl-2-pyridinium phenyltrimethoxysilane chloride, N-ethyl-2-pyridinium phenyl bromide Trimethoxysilane, N-ethyl-2-pyridinium phenyltrimethoxysilane iodide, N-propyl-2-pyridinium phenyltrimethoxysilane chloride, N-propyl-2-pyridinium phenyltrimethoxysilane bromide, N-propyl iodide -2-pyridinium pheny Trimethoxysilane, N-butyl-2-pyridinium phenyltrimethoxysilane chloride, N-butyl-2-pyridinium phenyltrimethoxysilane bromide, N-butyl-2-pyridinium phenyltrimethoxysilane iodide, N-methyl chloride 3-pyridinium phenyltrimethoxysilane, N-methyl-3-pyridiniumphenyltrimethoxysilane bromide, N-methyl-3-pyridiniumphenyltrimethoxysilane iodide, N-ethyl-3-pyridiniumphenyltrimethoxysilane chloride, odor N-ethyl-3-pyridinium phenyltrimethoxysilane, N-ethyl-3-pyridinium phenyltrimethoxysilane iodide, N-propyl-3-pyridiniumphenyltrimethoxysilane chloride, N-propyl-3-pyridinium bromide N-trimethoxysilane, N-propyl-3-pyridiniumphenyltrimethoxysilane iodide, N-butyl-3-pyridiniumphenyltrimethoxysilane chloride, N-butyl-3-pyridiniumphenyltrimethoxysilane bromide, N-iodide Butyl-3-pyridinium phenyltrimethoxysilane, N-methyl-4-pyridiniumphenyltrimethoxysilane chloride, N-methyl-4-pyridiniumphenyltrimethoxysilane bromide, N-methyl-4-pyridiniumphenyltrimethoxysilane iodide N-ethyl-4-pyridinium phenyltrimethoxysilane chloride, N-ethyl-4-pyridinium phenyltrimethoxysilane bromide, N-ethyl-4-pyridinium phenyltrimethoxysilane iodide, N-propyl-4-pyridinium chloride Muphenyltrimethoxysilane, N-propyl-4-pyridiniumphenyltrimethoxysilane bromide, N-propyl-4-pyridiniumphenyltrimethoxysilane iodide, N-butyl-4-pyridiniumphenyltrimethoxysilane chloride, N-bromide -Butyl-4-pyridinium phenyltrimethoxysilane, N-butyl-4-pyridinium phenyltrimethoxysilane iodide, N-methyl-2-quinolinium phenyltrimethoxysilane chloride, N-methyl-2-quinori bromide N-phenyltrimethoxysilane, N-methyl-2-quinolinium phenyltrimethoxysilane iodide, N-ethyl-2-quinolinium phenyltrimethoxysilane chloride, N-ethyl-2-quinolinium phenyltribromide Methoxysilane, N-ethyl-2-quinoiodide Ni-phenyltrimethoxysilane, N-methyl-3-quinoliniumphenyltrimethoxysilane chloride, N-methyl-3-quinoliniumphenyltrimethoxysilane bromide, N-methyl-3-quinoliniumphenyltriiodide Methoxysilane, N-ethyl-3-quinolinium phenyltrimethoxysilane chloride, N-ethyl-3-quinolinium phenyltrimethoxysilane bromide, N-ethyl-3-quinolinium phenyltrimethoxysilane iodide, N-methyl-4-quinolinium phenyltrimethoxysilane chloride, N-methyl-4-quinolinium phenyltrimethoxysilane bromide, N-methyl-4-quinolinium phenyltrimethoxysilane iodide, N-chloride Ethyl-4-quinolinium phenyltrimethoxysilane, N-ethyl-4-quinobromide N-phenyltrimethoxysilane, N-ethyl-4-quinoliniumphenyltrimethoxysilane iodide, N-methyl-5-quinoliniumphenyltrimethoxysilane chloride, N-methyl-5-quinoliniumphenyltribromide Methoxysilane, N-methyl-5-quinolinium phenyltrimethoxysilane iodide, N-ethyl-5-quinolinium phenyltrimethoxysilane chloride, N-ethyl-5-quinolinium phenyltrimethoxysilane bromide, N-ethyl-5-quinolinium phenyltrimethoxysilane iodide, N-methyl-6-quinolinium phenyltrimethoxysilane chloride, N-methyl-6-quinolinium phenyltrimethoxysilane bromide, N iodide -Methyl-6-quinolinium phenyltrimethoxysilane, N-ethyl-6-quinochloride Liniumphenyltrimethoxysilane, N-ethyl-6-quinoliniumphenyltrimethoxysilane bromide, N-ethyl-6-quinoliniumphenyltrimethoxysilane iodide, N-methyl-7-quinoliniumphenyl chloride Trimethoxysilane, N-methyl-7-quinolinium phenyltrimethoxysilane bromide, N-methyl-7-quinolinium phenyltrimethoxysilane iodide, N-ethyl-7-quinolinium phenyltrimethoxysilane chloride ,
N-ethyl-7-quinolinium phenyltrimethoxysilane bromide, N-ethyl-7-quinolinium phenyltrimethoxysilane iodide, N-methyl-8-quinolinium phenyltrimethoxysilane chloride, N-bromide -Methyl-8-quinolinium phenyltrimethoxysilane, iodide N-methyl-8-quinoliniumphenyltrimethoxysilane, N-ethyl-8-quinoliniumphenyltrimethoxysilane, N-ethylbromide- 8-quinolinium phenyltrimethoxysilane, iodide N-ethyl-8-quinoliniumphenyltrimethoxysilane, N-methyl-1-isoquinolinium phenyltrimethoxysilane chloride, N-methyl-1-bromide Isoquinolinium phenyltrimethoxysilane, N-methyl-1-isoquinolinium phenyltrimethyl iodide Xylsilane, N-ethyl-1-isoquinolinium phenyltrimethoxysilane chloride, N-ethyl-1-isoquinolinium phenyltrimethoxysilane bromide, N-ethyl-1-isoquinolinium phenyltrimethoxy iodide Silane, N-methyl-3-isoquinolinium phenyltrimethoxysilane chloride, N-methyl-3-isoquinolinium phenyltrimethoxysilane bromide, N-methyl-3-isoquinolinium phenyltrimethoxy iodide Silane, N-ethyl-3-isoquinolinium phenyltrimethoxysilane chloride, N-ethyl-3-isoquinolinium phenyltrimethoxysilane bromide, N-ethyl-3-isoquinolinium phenyltrimethoxy iodide Silane, N-methyl-4-isoquinolinium phenyltrimethoxysilane chloride, N-bromide Methyl-4-isoquinolinium phenyltrimethoxysilane, iodide N-methyl-4-isoquinoliniumphenyltrimethoxysilane, N-ethyl-4-isoquinoliniumphenyltrimethoxysilane chloride, N-bromide Ethyl-4-isoquinolinium phenyltrimethoxysilane, iodide N-ethyl-4-isoquinolinium phenyltrimethoxysilane, N-methyl-5-isoquinolinium phenyltrimethoxysilane, N-bromide Methyl-5-isoquinolinium phenyltrimethoxysilane, iodide N-methyl-5-isoquinolinium phenyltrimethoxysilane, N-ethyl-5-isoquinolinium phenyltrimethoxysilane, N-bromide Ethyl-5-isoquinolinium phenyltrimethoxysilane, iodide N-ethyl-5-isoxy Norinium phenyltrimethoxysilane, N-methyl-6-isoquinolinium phenyltrimethoxysilane chloride, N-methyl-6-isoquinolinium phenyltrimethoxysilane bromide, N-methyl-6-isooxy iodide Norinium phenyltrimethoxysilane, N-ethyl-6-isoquinolinium phenyltrimethoxysilane chloride, N-ethyl-6-isoquinolinium phenyltrimethoxysilane bromide, N-ethyl-6-isooxyiodide Norinium phenyltrimethoxysilane, N-methyl-7-isoquinolinium phenyltrimethoxysilane chloride, N-methyl-7-isoquinolinium phenyltrimethoxysilane bromide, N-methyl-7-isoxyiodide Norinium phenyltrimethoxysilane, N-ethyl-7-isoquinolinium phenyl chloride Methoxysilane, N-ethyl-7-isoquinoliniumphenyltrimethoxysilane bromide, N-ethyl-7-isoquinoliniumphenyltrimethoxysilane iodide, N-methyl-8-isoquinoliniumphenyltrichloride Methoxysilane, N-methyl-8-isoquinolinium phenyltrimethoxysilane bromide, N-methyl-8-isoquinolinium phenyltrimethoxysilane iodide, N-ethyl-8-isoquinolinium phenyltrichloride Methoxysilane, N-ethyl-8-isoquinolinium phenyltrimethoxysilane bromide, N-ethyl-8-isoquinolinium phenyltrimethoxysilane iodide, N-methyl-2-pyridinium benzyltrimethoxysilane chloride, N-methyl-2-pyridinium benzyltrimethoxysilane bromide, N-iodide Tyl-2-pyridinium benzyltrimethoxysilane, N-ethyl-2-pyridinium benzyltrimethoxysilane chloride, N-ethyl-2-pyridinium benzyltrimethoxysilane bromide, N-ethyl-2-pyridinium benzyltrimethoxysilane iodide N-propyl-2-pyridinium benzyltrimethoxysilane chloride, N-propyl-2-pyridinium benzyltrimethoxysilane bromide, N-propyl-2-pyridinium benzyltrimethoxysilane iodide, N-butyl-2-pyridinium chloride Benzyltrimethoxysilane, N-butyl-2-pyridinium benzyltrimethoxysilane bromide, N-butyl-2-pyridinium benzyltrimethoxysilane iodide, N-methyl-3-pyridinium benzyltrimethoxysilane chloride, bromide N-methyl-3-pyridinium benzyltrimethoxysilane, N-methyl-3-pyridinium benzyltrimethoxysilane iodide, N-ethyl-3-pyridinium benzyltrimethoxysilane chloride, N-ethyl-3-pyridinium benzyltribromide Methoxysilane, N-ethyl-3-pyridinium benzyltrimethoxysilane iodide, N-propyl-3-pyridinium benzyltrimethoxysilane chloride, N-propyl-3-pyridinium benzyltrimethoxysilane bromide, N-propyl iodide 3-pyridinium benzyltrimethoxysilane, N-butyl-3-pyridinium benzyltrimethoxysilane chloride, N-butyl-3-pyridinium benzyltrimethoxysilane bromide, N-butyl-3-pyridinium benzyltrimethoxysilane iodide N-methyl-4-pyridinium benzyltrimethoxysilane chloride, N-methyl-4-pyridinium benzyltrimethoxysilane bromide, N-methyl-4-pyridinium benzyltrimethoxysilane iodide, N-ethyl-4-pyridinium chloride Benzyltrimethoxysilane, N-ethyl-4-pyridinium benzyltrimethoxysilane bromide, N-ethyl-4-pyridinium benzyltrimethoxysilane iodide, N-propyl-4-pyridinium benzyltrimethoxysilane chloride, N-bromide Propyl-4-pyridinium benzyltrimethoxysilane, N-propyl-4-pyridinium benzyltrimethoxysilane iodide, N-butyl-4-pyridinium benzyltrimethoxysilane chloride, N-butyl-4-pyridinium benzyltrimethoxy bromide Silane, N-butyl-4-pyridinium benzyltrimethoxysilane iodide, N-methyl-2-quinolinium benzyltrimethoxysilane chloride, N-methyl-2-quinolinium benzyltrimethoxysilane bromide, N iodide -Methyl-2-quinolinium benzyltrimethoxysilane, N-ethyl-2-quinolinium benzyltrimethoxysilane chloride, N-ethyl-2-quinolinium benzyltrimethoxysilane bromide, N-ethyl iodide- 2-quinolinium benzyltrimethoxysilane, N-methyl-3-quinolinium benzyltrimethoxysilane chloride, N-methyl-3-quinolinium benzyltrimethoxysilane bromide, N-methyl-3-iodide iodide Norinium benzyltrimethoxysilane, N-ethyl-3-quinolinium benzyltrimethoxy chloride Sisilane, N-ethyl-3-quinolinium benzyltrimethoxysilane bromide, N-ethyl-3-quinolinium benzyltrimethoxysilane iodide, N-methyl-4-quinolinium benzyltrimethoxysilane chloride, odor N-methyl-4-quinolinium benzyltrimethoxysilane, N-methyl-4-quinolinium benzyltrimethoxysilane iodide, N-ethyl-4-quinolinium benzyltrimethoxysilane chloride, N-bromide Ethyl-4-quinolinium benzyltrimethoxysilane, N-ethyl-4-quinolinium benzyltrimethoxysilane iodide, N-methyl-5-quinolinium benzyltrimethoxysilane chloride, N-methyl-5 bromide -Quinolinium benzyltrimethoxysilane, N-methyl-5-quinolinium benzyltrimet iodide Sisilane, N-ethyl-5-quinolinium benzyltrimethoxysilane chloride, N-ethyl-5-quinolinium benzyltrimethoxysilane bromide, N-ethyl-5-quinolinium benzyltrimethoxysilane iodide, chloride N-methyl-6-quinolinium benzyltrimethoxysilane, N-methyl-6-quinolinium benzyltrimethoxysilane bromide, N-methyl-6-quinolinium benzyltrimethoxysilane iodide, N-ethyl chloride -6-quinolinium benzyltrimethoxysilane, N-ethyl-6-quinolinium benzyltrimethoxysilane bromide, N-ethyl-6-quinolinium benzyltrimethoxysilane iodide, N-methyl-7- chloride Quinolinium benzyltrimethoxysilane, N-methyl-7-quinolinium benzyltrimet bromide Sisilane, N-methyl-7-quinolinium benzyltrimethoxysilane iodide, N-ethyl-7-quinolinium benzyltrimethoxysilane chloride, N-ethyl-7-quinolinium benzyltrimethoxysilane bromide, iodine N-ethyl-7-quinolinium benzyltrimethoxysilane, N-methyl-8-quinolinium benzyltrimethoxysilane chloride, N-methyl-8-quinolinium benzyltrimethoxysilane bromide, N-iodide Methyl-8-quinolinium benzyltrimethoxysilane, N-ethyl-8-quinolinium benzyltrimethoxysilane chloride, N-ethyl-8-quinolinium benzyltrimethoxysilane bromide, N-ethyl-8 iodide -Quinolinium benzyltrimethoxysilane, N-methyl-1-isoquinolinium benzyltrichloride Methoxysilane, N-methyl-1-isoquinolinium benzyltrimethoxysilane bromide,
N-methyl-1-isoquinolinium benzyltrimethoxysilane iodide, N-ethyl-1-isoquinolinium benzyltrimethoxysilane chloride, N-ethyl-1-isoquinolinium benzyltrimethoxysilane bromide, N-ethyl-1-isoquinolinium benzyltrimethoxysilane iodide, N-methyl-3-isoquinolinium benzyltrimethoxysilane chloride, N-methyl-3-isoquinolinium benzyltrimethoxysilane bromide, N-methyl-3-isoquinolinium benzyltrimethoxysilane iodide, N-ethyl-3-isoquinolinium benzyltrimethoxysilane chloride, N-ethyl-3-isoquinolinium benzyltrimethoxysilane bromide, N-ethyl-3-isoquinolinium benzyltrimethoxysilane iodide, N-methyl-4 chloride Isoquinolinium benzyltrimethoxysilane, N-methyl-4-isoquinolinium benzyltrimethoxysilane bromide, N-methyl-4-isoquinolinium benzyltrimethoxysilane iodide, N-ethyl-4-chloride Isoquinolinium benzyltrimethoxysilane, N-ethyl-4-isoquinolinium benzyltrimethoxysilane bromide, N-ethyl-4-isoquinolinium benzyltrimethoxysilane iodide, N-methyl-5-chloride Isoquinolinium benzyltrimethoxysilane, N-methyl-5-isoquinolinium benzyltrimethoxysilane bromide, N-methyl-5-isoquinolinium benzyltrimethoxysilane iodide, N-ethyl-5-chloride Isoquinolinium benzyltrimethoxysilane, N-ethyl-5-isoquinolinium bromide Diltrimethoxysilane, N-ethyl-5-isoquinolinium benzyltrimethoxysilane iodide, N-methyl-6-isoquinolinium benzyltrimethoxysilane chloride, N-methyl-6-isoquinolinium bromide Benzyltrimethoxysilane, N-methyl-6-isoquinolinium benzyltrimethoxysilane iodide, N-ethyl-6-isoquinolinium benzyltrimethoxysilane chloride, N-ethyl-6-isoquinolinium bromide Benzyltrimethoxysilane, N-ethyl-6-isoquinolinium iodide benzyltrimethoxysilane, N-methyl-7-isoquinolinium chloride benzyltrimethoxysilane, N-methyl-7-isoquinolinium bromide Benzyltrimethoxysilane, N-methyl-7-isoquinolinium benzyltrimethoxysilane iodide Run, N-ethyl-7-isoquinolinium benzyltrimethoxysilane chloride, N-ethyl-7-isoquinolinium benzyltrimethoxysilane bromide, N-ethyl-7-isoquinolinium benzyltrimethoxy iodide Silane, N-methyl-8-isoquinolinium benzyltrimethoxysilane chloride, N-methyl-8-isoquinolinium benzyltrimethoxysilane bromide, N-methyl-8-isoquinolinium benzyltrimethoxy iodide Silane, N-ethyl-8-isoquinolinium benzyltrimethoxysilane chloride, N-ethyl-8-isoquinolinium benzyltrimethoxysilane bromide, N-ethyl-8-isoquinolinium benzyltrimethoxy iodide Although silane etc. are mentioned, it is not necessarily limited to the silicon-containing compound illustrated here, General formula (3 No problem as long as the case where Y is a heterocyclic aromatic quaternary ammonium ion derived from the group represented by the general formula (15) in the. The alkyl groups such as propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group and the like exemplified here are not limited to linear n-forms, but are isoforms, sec-forms, tert-forms. It may be branched or cyclic like a body.

  The silicon-containing compound in the case where Y in the general formula (3) is a group derived from a quaternary ammonium ion represented by the general formulas (11) to (15) is a counter anion of the various compounds described above. Various halide ions include, for example, carbonate ions, nitrate ions, sulfate ions, phosphate ions, borate ions, formate ions, carboxylate ions such as acetate ions, trifluoromethanesulfonate ions, sulfones such as p-toluenesulfonate ions. Also included are organic acid ions such as acid ions, mono- or dialkyl phosphate ions, mono- or dialkyl borate ions and other counter anions.

（式中、Ｒ^３、Ｒ^４及びＹは上記に同じ。）で示されるのジシラザン構造のものである含ケイ素化合物も、一般式（３）で示される含ケイ素化合物に含まれる。 Furthermore, the silicon-containing compound represented by the above general formula (3) is exemplified by a silicon-containing compound in which both R ⁴ and Z in the general formula (3) are halogen atoms and a silicon-containing compound in which an alkoxy group is an alkoxy group. However, the present invention is not limited to these specific examples. For example, a silicon-containing compound in which two R ⁴ and Z are both hydroxyl groups, or two R ⁴ are straight-chain, A silicon-containing compound which is a branched or cyclic alkyl group and Z is an allyl group; and R ⁴ is a linear, branched or cyclic alkyl group having 1 to 8 carbon atoms, and Z is The silicon-containing compound which is a silazane group represented by the general formula (A), that is, the general formula (20)

(In the formula, R ³ , R ⁴ and Y are the same as above.) A silicon-containing compound having a disilazane structure is also included in the silicon-containing compound represented by the general formula (3).

（式中、Ｒ^３’は炭素数１〜８のアルキレン基を表し、Ｒ^２２は炭素数１〜８の直鎖状、分枝状若しくは環状のアルキル基を表し、Ｒ^１１、Ｒ^１２、Ｒ^１３及びＸ⁻は上記に同じ。）で示される含ケイ素化合物が好ましく、その中でも、式（１７）

で示される含ケイ素化合物がより好ましい。 Among the silicon-containing compounds represented by the general formula (3) described so far, from the viewpoint of obtaining advantageous effects different from the effects of the present invention, such as easy acquisition and synthesis of silicon-containing compounds. In this case, R ³ in the general formula (3) is an alkylene group having 1 to 8 carbon atoms, and two R ⁴ and Z are both linear, branched or cyclic alkoxy groups having 1 to 8 carbon atoms. And a group derived from a tertiary amine represented by Y or a group derived from a quaternary ammonium ion is an acyclic quaternary ammonio group represented by the general formula (11), Formula (16)

(In the formula, R ³ ′ represents an alkylene group having 1 to 8 carbon atoms, R ²² represents a linear, branched or cyclic alkyl group having 1 to 8 carbon atoms, and R ¹¹ , R ¹² , R ¹³ and X ⁻ are the same as above.) Are preferred, and among these, the formula (17)

The silicon-containing compound represented by is more preferable.

  The silica used for the reaction with the silicon-containing compound represented by the general formula (3) can be reacted with the silicon-containing compound represented by the general formula (3) and has a pore in its shape. There is no particular limitation, and there are usually fine particles of about 1 μm to 1000 μm, spherical particles having an average particle size of about 0.1 mm to 10 mm, cylindrical shapes, thin film shapes, etc., and silica usually used in this field is used. More specifically, easily available silica gel for separation, mesoporous silica having a relatively uniform pore size, and the like can be used.

The pore diameter of the silica is not particularly limited, but usually silica having a pore diameter of 0.5 nm to 500 nm is preferable, and among them, the cyclic sulfite ester represented by the general formula (2) is produced in a higher yield. Silica having a pore diameter of 1 nm to 100 nm is more preferable in that it can be expected. There is no particular limitation on the specific surface area of the silica, but no problem on silica with any of the specific surface area, typically a specific surface area of ^{10m 2} / g~1500m 2 / g approximately, among others 100m ² / g~1500m ² It is preferable to use the one of about / g. As for the calculation method of these numerical values, the BJT method may be applied to the pore diameter (average pore diameter), and the BET method may be applied to the specific surface area.

（式中、Ｒ^３、Ｒ^４及びＹは上記に同じ。）のような模式図で表すこともできる。 The silica catalyst surface-modified with a tertiary amine group or a quaternary ammonium ionic group obtained by the reaction of the silicon-containing compound represented by the general formula (3) with the silica is obtained by the reaction as described above. A group derived from the silicon-containing compound is supported by a chemical bonding reaction between the silicon-containing compound and a surface silanol group in silica, and specifically, the general formula (4) derived from the silicon-containing compound. , (5) or (6) having a structural unit introduced with a group. Although it is difficult to represent the structure of the silica catalyst, for example, the silica catalyst has the general formula (I), (II) or (III).

(In the formula, R ³ , R ⁴ and Y are the same as above).

  The supported amount of the structural unit derived from the silicon-containing compound represented by the general formula (3) in the silica catalyst may be arbitrary, but the amount of the silica catalyst used is derived from the silicon-containing compound in the silica catalyst as described later. Since it is determined by the total number of moles of nitrogen atoms contained in the structural unit into which the group has been introduced, if the amount is too small, problems such as an excessive amount of silica catalyst may occur. Therefore, the weight of nitrogen atoms is usually set to 0.01 wt% to 10 wt%, preferably 0.2 wt% to 4 wt% with respect to the weight of the silica catalyst. Further, the amount ratio of these components in the reaction of the silicon-containing compound represented by the general formula (3) and silica is appropriately determined so that the supported amount of the structural unit falls within the above numerical range. The weight and total number of moles of nitrogen atoms in the silica catalyst can be confirmed by a method such as elemental analysis by gas chromatography or the like.

The silica catalyst surface-modified with a tertiary amine group or a quaternary ammonium ionic group is obtained by reacting a silicon-containing compound represented by the general formula (3) with silica on the surface of silica. Since the group derived from the compound is supported, the pore diameter and specific surface area of the pores in the silica catalyst are compared with the pore diameter and specific surface area of silica (raw silica) to be reacted with the silicon-containing compound represented by the general formula (3). In this case, although there are some fluctuations, there is no limitation on the pore diameter and specific surface area of the pores in the silica catalyst, and any pore diameter or specific surface area can be used as long as it is a silica catalyst synthesized from silica usually used in this field. It can be anything. In consideration of availability, ease of handling, and improvement in yield of the cyclic sulfite represented by the general formula (2), the pore diameter of the pores in the silica catalyst is usually 0.5 nm to 500 nm, Preferably, it is 1 nm to 100 nm. The specific surface area of the silica catalyst is typically ^{10m 2} / g~1500m 2 / g approximately, among others 100m ² / g~1500m of about ² / g are preferred. Note that, as described above, the BJT method or the BET method may be applied to the calculation method of these numerical values.

  In the present invention, after introducing a group derived from a silicon-containing compound into silica, a residual silanol group to which a group derived from a silicon-containing compound could not be introduced is treated with an end capping agent such as a trimethylsilylating agent ( End-capped) can also be used, and the silica catalyst in the present invention includes a silica catalyst obtained by crushing (protecting) part of silanol groups by such end-capping treatment.

  The amount of the silica catalyst thus obtained in the present invention is such that the epoxide represented by the general formula (1) with respect to the total number of moles of nitrogen atoms contained in the structural unit derived from the silicon-containing compound in the silica catalyst. It is usually 0.01 mol% to 10 mol%, preferably 0.1 mol% to 5 mol%, more preferably 0.2 mol% to 2 mol%, based on the number of moles. In addition, when the usage-amount of a silica catalyst is very small, it exists in the tendency for the yield of the cyclic sulfite ester shown by General formula (2) to fall.

  Thus, in the present invention, since a silica catalyst surface-modified with a tertiary amine group or a quaternary ammonium ionic group is used as a catalyst, the reaction can be performed for a long time (even if left), An excellent effect that does not exist in the conventional method, that is, reduction in the yield of cyclic sulfite due to decomposition of the product or the like can be suppressed.

  In the present invention, if necessary, the solvent (reaction solvent) may be any solvent that does not adversely affect the reaction of the raw materials and products. Specifically, for example, pentane, hexane, heptane, octane, etc. Non-polar organic solvents such as aliphatic hydrocarbons, aromatic non-polar organic solvents such as benzene, toluene and xylene, aromatic and / or aliphatic hydrocarbon mixed non-polar organic solvents such as petroleum benzine and ligroin Halogen-based non-polar organic solvents such as dichloromethane and chloroform, and ether-based non-polar organic solvents such as diethyl ether and tetrahydrofuran, etc., but the cyclic sulfite ester represented by the general formula (2), which is the target product, is hydrolyzed. These solvents are preferably subjected to a dehydration treatment. These solvents may be used alone or in combination of two or more, and the amount of the solvent to be used is not particularly limited. For example, the amount of the solvent is generally 0. 1 g with respect to 1 g of the epoxide represented by the general formula (1). 1 mL to 1000 mL, preferably 1 mL to 100 mL. Here, the system using a solvent has been described, but in the present invention, from the viewpoint of easy isolation and purification of the cyclic sulfite ester represented by the general formula (2), which is the target product, When the epoxide represented by a general formula (1) is a liquid, it is more preferable to carry out the reaction without a solvent.

  The reaction temperature in the present invention may be set to a temperature at which the epoxide represented by the general formula (1) reacts with sulfur dioxide, but the epoxide and sulfur dioxide react efficiently, and the general formula (3) It is desirable to set the temperature so that the cyclic sulfite represented by can be produced with good yield. Specifically, it is 0 degreeC-200 degreeC normally, for example, Preferably it is 60 degreeC-180 degreeC.

  The pressure during the reaction in the present invention may be set to a pressure at which the epoxide represented by the general formula (1) and sulfur dioxide react, but the epoxide and sulfur dioxide react efficiently, and the general formula ( It is desirable to set the pressure so that the cyclic sulfite represented by 3) can be produced with good yield. Specifically, for example, the pressure is usually 0.1 MPa to 2 MPa, preferably 0.1 MPa to 1 MPa. The method of the present invention is an advantageous reaction in that it does not require a high-pressure device as it does not require a high pressure as required by conventional methods. In addition, what is necessary is just to perform manufacture of the cyclic sulfite ester on pressurization conditions using the pressure | voltage resistant apparatus normally used in this field | area, such as a shield tube and an autoclave.

  The reaction time in the present invention may be affected by the amount of sulfur dioxide used with respect to the epoxide represented by the general formula (1), the type and amount of silica catalyst, the presence of a solvent, the reaction temperature, the pressure during the reaction, and the like. Therefore, although it cannot be generally stated, it is usually set in the range of 1 hour to 168 hours, preferably 24 hours to 96 hours. Even if the effect of the present invention is that the reaction is carried out for a long time (even if it is allowed to stand), the above reaction time is exceeded even from the viewpoint that the production of by-products due to decomposition of the product can be suppressed. The reaction can be done (even if left unattended). Specifically, even if the reaction is continued for 170 hours or more (even if it is allowed to stand), it is represented by the general formula (3), which is the target product, without causing an extreme decrease in yield as in the conventional method. Cyclic sulfites can be produced.

  Examples of the method for isolating and purifying the cyclic sulfite represented by the general formula (3) include an isolation and purification method by a post-treatment operation usually performed in this field. Specifically, for example, after removing the silica catalyst remaining in the reaction system by filtration or the like, the solvent used in removing the silica catalyst may be distilled off. In some cases, recrystallization may be performed with an appropriate solvent. The target product may be isolated and purified. Further, for example, when the reaction is carried out without a solvent, the target product can be easily isolated and purified by distilling the reaction solution as it is. Furthermore, the reaction solution can be purified by an operation such as column chromatography.

  EXAMPLES Hereinafter, although this invention is demonstrated concretely based on an Example, this invention is not limited at all by these examples.

Synthesis Example 1 Synthesis of ethyl iodide dimethylpropylammonium trimethoxysilane To a solution obtained by adding 50 mL of acetonitrile to 9.5 g (46 mmol) of dimethylaminopropyltrimethoxysilane (manufactured by Aldrich), 8.1 g (52 mmol) of ethyl iodide was added. The solution was added dropwise and reacted for 24 hours under heating and refluxing conditions. After completion of the reaction, the reaction solution was cooled, and the reaction solution was concentrated to obtain 15.9 g (44 mmol) (yield: 95%) of ethyldimethylpropylammonium trimethoxysilane iodide as a concentrated residue. The measurement result of ¹ H-NMR is shown below.
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm): 0.71 (2H, t, SiCH ₂ ), 1.44 (3H, t, CH ₃ ), 1.84 (2H, m, CH ₂ ) , 3.34 (6H, s, 2 × NCH ₃ ), 3.52 (2H, t, CH ₂ N), 3.58 (9H, s, 3 × OCH ₃ ), 3.69 (2H, q, NCH ₂ )

Synthesis Example 2 Synthesis of silica catalyst surface-modified with ethyl dimethylpropylammonium iodide group (quaternary ammonium ionic group) 50 mL of chloroform was added to 2.0 g of mesoporous silica (TMPS-4: manufactured by Taiyo Kagaku Co., Ltd.). To the added solution, 2.9 g (8.0 mmol) of ethyldimethylpropylammonium trimethoxysilane obtained in Synthesis Example 1 was added, and reacted for 24 hours under heating and refluxing conditions. After completion of the reaction, the reaction solution is filtered and the desired silica catalyst is collected by filtration, and the silica catalyst obtained is washed with chloroform and then vacuum-dried, whereby the surface-modified silica with ethyldimethylpropylammonium iodide group is obtained. 2.8 g of catalyst was obtained. When the obtained silica catalyst was measured by elemental analysis, the content of nitrogen atoms in the silica catalyst was 1.4% by weight. Further, the pore diameter (average pore diameter) in the raw material mesoporous silica was calculated by the BJT method and the specific surface area was calculated by the BET method, and they were 3.80 nm and 1005 m ² / g, respectively. Further, the pore diameter (average pore diameter) and specific surface area of the silica catalyst surface-modified with an ethyldimethylpropylammonium iodide group were 3.28 nm and 809 m ² / g, respectively, by the same calculation method.

Synthesis Examples 3 to 8 Synthesis of Silica Catalysts Surface-Modified with Ethyldimethyldimethylammonium Iodide Group (Quaternary Ammonium Ionic Group) In Synthesis Examples 3 to 8, silica as shown in Table 1 was used as the raw material silica. A silica catalyst surface-modified with an ethyldimethylpropylammonium iodide group was obtained in the same manner as in Synthesis Example 2 except that it was used. Example of synthesis in combination with pore diameter (average pore diameter) and specific surface area of raw silica, and pore diameter (average pore diameter) and specific surface area of silica catalyst surface-modified with ethyldimethylpropylammonium iodide group The results of 2-8 are shown in Table 1.

Synthesis Examples 9 to 10 Synthesis of silica catalysts surface-modified with an ethyldimethyldimethylammonium iodide group (quaternary ammonium ionic group) In Synthesis Examples 9 to 10, the ethyldimethylpropylammonium iodide trioxide used in Synthesis Example 2 was used. The same silica as in Synthesis Example 2 was used except that the amount of methoxysilane used was changed to 0.36 g (1.0 mmol) in Synthesis Example 9 and 0.7 g (2.0 mmol) in Synthesis Example 10. By performing the operation, a silica catalyst whose surface was modified with an ethyldimethylpropylammonium iodide group was obtained. Example of synthesis in combination with pore diameter (average pore diameter) and specific surface area of raw silica, and pore diameter (average pore diameter) and specific surface area of silica catalyst surface-modified with ethyldimethylpropylammonium iodide group The results of 9-10 are shown in Table 2.

Synthesis Example 11 Synthesis of Silica Catalyst with Residual Silanol Group Capped with Trimethylsilyl Group To a solution obtained by adding 50 mL of chloroform to 1.0 g of silica catalyst surface-modified with ethyldimethylpropylammonium iodide obtained by the method of Synthesis Example 10 Then, 0.1 g (1.0 mmol) of trimethylmethoxysilane was added and reacted under heating under reflux conditions for 24 hours. After completion of the reaction, the reaction solution is filtered to collect the target silica catalyst, and the resulting silica catalyst is washed with chloroform and then vacuum-dried so that the remaining silanol groups are capped with trimethylsilyl groups. 1.0 g of silica catalyst was obtained. When the obtained silica catalyst was measured by elemental analysis, the content of nitrogen atoms in the silica catalyst was 0.72% by weight. Further, the pore diameter (average pore diameter) of the surface-modified silica catalyst in which the residual silanol groups were capped with trimethylsilyl groups was calculated by the BJT method, and the specific surface area was calculated by the BET method. It was 753 m ² / g.

Example 1 Synthesis of propylene sulfite using EtIDMAPr-TMPS-4 (mesoporous silica surface-modified with ethyldimethylpropylammonium iodide group) catalyst Silica catalyst obtained in Synthesis Example 2 (1.0 mmol / g EtIDMAPr-TMPS) -4 catalyst) 72 mg (0.07 mmol in terms of nitrogen atom weight), 829 mg (14 mmol) of propylene oxide, and 100 μL of mesitylene, which is an internal standard substance, were charged into a pressure-resistant glass container, cooled to −50 ° C., and sulfur dioxide gas was integrated. 342 mL (20 ° C., 14 mmol) was introduced with a flow meter {the relative value of the total number of moles of nitrogen atoms in the silica catalyst relative to the number of moles of propylene oxide (hereinafter referred to as catalyst relative amount) was 0.5 mol%. there were}. Subsequently, after sealing this reaction container, it was made to react at 100 degreeC for arbitrary time. The pressure during the reaction was 0.5 MPa. After completion of the reaction, the reaction solution is cooled to room temperature and returned to normal pressure, and then the reaction solution is diluted with 10 mL of chloroform, and the diluted solution is filtered with a membrane filter and 30 mL of chloroform to remove and wash the catalyst. The solution was analyzed and quantified by gas chromatography. For gas chromatography analysis and quantification, GL Sciences TC-1 (0.25 ID × 60 m) was used for the column, the temperature was raised from 40 ° C. to 300 ° C., and measured with an FID detector. Was quantified from a calibration curve of propylene sulfite prepared as a standard substance. The by-product was quantified using the same calibration curve as propylene sulfite. The results are shown in Table 3, and a graph of the change over time in the reaction situation is also shown in FIG. In the figure,-○-represents propylene oxide (PO),-□-represents propylene sulfite (PS), and -Δ- represents a by-product (by-pro) (in FIGS. 2 to 17 below). The same is true.)

Examples 2 to 8 Synthesis of propylene sulfite using the silica catalyst obtained in Synthesis Examples 2 to 8 In Examples 2 to 8, except that the amount of the silica catalyst used and / or the type of the silica catalyst was changed, it was carried out. Synthesis was carried out in the same manner as in Example 1. That is, Example 2 was carried out in the same manner as in Example 1 except that 0.098 mmol of the amount of the silica catalyst obtained in Synthesis Example 2 was used in terms of the amount of nitrogen atoms (the relative amount of the catalyst was 0.7 mol%). ) In Examples 3 to 8, propylene sulfite was obtained in the same manner as in Example 1 except that 0.07 mmol of the amount of each of the silica catalysts obtained in Synthesis Examples 3 to 8 was used in terms of the amount of nitrogen atoms. (Relative amounts of catalyst are all 0.5 mol%). While showing the result in Tables 4-10, the graph of the time-dependent change of the reaction condition is combined with FIGS. The analysis and quantification of propylene sulfite and by-products were performed according to the method of Example 1.

Example 9 Synthesis of propylene sulfite using the silica catalyst obtained in Synthesis Example 2 Example 9 was the same as Example 1 except that the amount of silica catalyst obtained in Synthesis Example 2 was changed. Synthesis was performed. That is, the same procedure as in Example 1 was carried out except that 0.14 mmol of the amount of the silica catalyst obtained in Synthesis Example 2 was used in terms of the amount of nitrogen atoms (the relative amount of the catalyst was 1.0 mol%), and propylene sulfite. Was synthesized. The results are shown in Table 11, and a graph of the change over time in the reaction situation is also shown in FIG. The analysis and quantification of propylene sulfite and by-products were performed according to the method of Example 1.

Examples 10 to 12 Synthesis of propylene sulfite using the silica catalysts obtained in Synthesis Examples 9 to 11 In Examples 10 to 12, the type of silica catalyst was changed (Example 10: obtained in Synthesis Example 9). Propylene sulfite was synthesized in the same manner as in Example 1 except for the silica catalyst, Example 11: the silica catalyst obtained in Synthesis Example 10, and Example 12: the silica catalyst obtained in Synthesis Example 11. Nitrogen atomic weight conversion: 0.07 mmol, catalyst relative amount: 0.5 mol%). The results are shown in Tables 12 to 14, and graphs of changes over time in the reaction situation are also shown in FIGS. The analysis and quantification of propylene sulfite and by-products were performed according to the method of Example 1.

Comparative Example 1 18 mg (0.07 mmol) of tetraethylammonium iodide, 829 mg (14 mmol) of propylene oxide, and 100 μL of mesitylene as an internal standard substance as a catalyst for synthesis of propylene sulfite using tetraethylammonium iodide as a catalyst in a pressure-resistant glass container After charging and cooling to −50 ° C., 342 mL (20 ° C., 14 mmol) of sulfur dioxide gas was introduced with an integrating flow meter (relative value of tetraethylammonium iodide to the number of moles of propylene oxide (hereinafter referred to as catalyst relative amount (comparison)). Example))) was 0.5 mol%). Subsequently, after sealing this reaction container, it was made to react at 100 degreeC for arbitrary time. The pressure during the reaction was 0.5 MPa. After completion of the reaction, the reaction solution was cooled to room temperature and returned to normal pressure, and then the reaction solution was diluted with 40 mL of chloroform, and this solution was analyzed and quantified by gas chromatography. The analysis and quantification by gas chromatography were performed according to the method of Example 1. The results are shown in Table 15, and a graph of the change over time in the reaction situation is also shown in FIG.

Comparative Examples 2 to 5 Synthesis of propylene sulfite using tetraethylammonium iodide or pyridine as a catalyst In Comparative Examples 2 to 3, the catalyst relative amount (comparative example) of tetraethylammonium iodide was variously changed (Comparative Example 2: 1. Except for 0 mol%, Comparative Example 3: 2.5 mol%), the same method as in Comparative Example 1 was carried out. In Comparative Example 4, the reaction temperature was changed to 150 ° C., and the same method as in Comparative Example 1 was carried out. In Comparative Example 5, propylene sulfite was synthesized in the same manner as in Comparative Example 1 except that pyridine was used as the catalyst of the conventional method (relative amount of catalyst (comparative example) 0.5 mol%). . The results are shown in Tables 16 to 19, and graphs of changes over time in the reaction situation are also shown in FIGS. The analysis and quantification of propylene sulfite and by-products were performed according to the method of Comparative Example 1.

  From the results of Examples 1 to 12 and Comparative Examples 1 to 5, (1) When the reaction was carried out for a long time using the catalyst used in the conventional method (when left), the generation of by-products was the cause. In addition, it was found that the yield of the cyclic sulfite ester was significantly reduced, and (2) the reaction was carried out for a long time by using a catalyst supported on silica instead of using the catalyst used in the conventional method. (Even if left), the formation of by-products was suppressed, and it was found that the yield was not significantly reduced. From this result, the present invention is advantageous not only in that it does not require strict time management, but also in that it is easy to recover and reuse the silica catalyst, which is advantageous for industrial scale production of cyclic sulfites. It turns out that it is a method.

  The production method of the present invention enables industrial scale production of a cyclic sulfite useful for, for example, an electrolyte for a lithium battery, and the catalyst of the present invention makes it easier to use such a cyclic sulfite. It is a catalyst that makes it possible to produce.

It is a figure which shows the time-dependent change of the reaction condition of Example 1 as a graph. It is a figure which shows the time-dependent change of the reaction condition of Example 2 as a graph. It is a figure which shows the time-dependent change of the reaction condition of Example 3 as a graph. It is a figure which shows the time-dependent change of the reaction condition of Example 4 as a graph. It is a figure which shows the time-dependent change of the reaction condition of Example 5 as a graph. It is a figure which shows the time-dependent change of the reaction condition of Example 6 as a graph. It is a figure which shows the time-dependent change of the reaction condition of Example 7 as a graph. It is a figure which shows the time-dependent change of the reaction condition of Example 8 as a graph. It is a figure which shows the time-dependent change of the reaction condition of Example 9 as a graph. It is a figure which shows the time-dependent change of the reaction condition of Example 10 as a graph. It is a figure which shows the time-dependent change of the reaction condition of Example 11 as a graph. It is a figure which shows the time-dependent change of the reaction condition of Example 12 as a graph. It is a figure which shows the time-dependent change of the reaction condition of the comparative example 1 as a graph. It is a figure which shows the time-dependent change of the reaction condition of the comparative example 2 as a graph. It is a figure which shows the time-dependent change of the reaction condition of the comparative example 3 as a graph. It is a figure which shows the time-dependent change of the reaction condition of the comparative example 4 as a graph. It is a figure which shows the time-dependent change of the reaction condition of the comparative example 5 as a graph.

Claims (8)

General formula (1)

(Wherein R ¹ and R ² are each independently a hydrogen atom, a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms which may be substituted by a halogen atom, or a halogen atom. R ¹ and R ² form a ring having 5 to 10 carbon atoms which may have a halogen atom as a substituent together with the carbon atom to which R ¹ and R ² are bonded. The epoxide and sulfur dioxide represented by quaternary ammonium ion having a structural unit represented by the following general formula (4), the following general formula (5), or the following general formula (6) Wherein the reaction is carried out in the presence of a silica catalyst surface-modified with a group.

(Wherein R ¹ and R ² are the same as described above).
General formula (4):

{Wherein R ³ represents a linear alkylene group having 2 to 4 carbon atoms, R ⁴ independently represents a linear alkoxy group having 1 to 6 carbon atoms, and Y represents Formula (11)

(In the formula, R ¹¹ , R ¹² and R ¹³ each independently represents a linear alkyl group having 1 to 4 carbon atoms, and X ⁻ is selected from a chloride ion, a bromide ion and an iodide ion. Represents a halide ion.) And represents an acyclic quaternary ammonio group. }
General formula (5):

(Wherein R ³ , R ⁴ and Y are the same as above)
General formula (6):

(In the formula, R ³ and Y are the same as above.) Surface-modified silica catalyst in the previous SL quaternary ammonium ionic group is represented by the general formula (16)

(In the formula, R ^{3 ′} represents a linear alkylene group having 2 to 4 carbon atoms, and R ¹¹ , R ¹² and R ¹³ are each independently a linear alkyl group having 1 to 4 carbon atoms. R ²² represents a linear alkyl group having 1 to 6 carbon atoms, and X ⁻ represents a halide ion selected from chloride ion, bromide ion and iodide ion. The production method according to claim 1, which is obtained by reacting a silicon compound and silica. Surface-modified silica catalyst in the previous SL quaternary ammonium ionic group is represented by the formula (17)

The manufacturing method of Claim 1 which is obtained by making the silicon-containing compound shown by and silica react. The epoxide represented by the general formula (1) is represented by the general formula (18).

(Wherein R ^{1 ′} represents a hydrogen atom or a methyl group), and the cyclic sulfite represented by the general formula (2) is represented by the general formula (19)

The manufacturing method according to claim 1, wherein R ^{1 ′} is the same as above. General formula (1) containing silica surface-modified with a quaternary ammonium ionic group having a structural unit represented by the following general formula (4), the following general formula (5), or the following general formula (6 )

(Wherein R ¹ and R ² are each independently a hydrogen atom, a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms which may be substituted by a halogen atom, or a halogen atom. R ¹ and R ² form a ring having 5 to 10 carbon atoms which may have a halogen atom as a substituent together with the carbon atom to which R ¹ and R ² are bonded. By reacting the epoxide represented by (2) with sulfur dioxide.

(Wherein R ¹ and R ² are the same as above), a catalyst used in the synthesis of the cyclic sulfite ester.
General formula (4):

{Wherein R ³ represents a linear alkylene group having 2 to 4 carbon atoms, R ⁴ independently represents a linear alkoxy group having 1 to 6 carbon atoms, and Y represents Formula (11)

(In the formula, R ¹¹ , R ¹² and R ¹³ each independently represents a linear alkyl group having 1 to 4 carbon atoms, and X ⁻ is selected from a chloride ion, a bromide ion and an iodide ion. Represents a halide ion.) And represents an acyclic quaternary ammonio group. }
General formula (5):

(Wherein R ³ , R ⁴ and Y are the same as above)
General formula (6):

(In the formula, R ³ and Y are the same as above.) The catalyst containing silica surface-modified with a quaternary ammonium ionic group is represented by the general formula (16):

(In the formula, R ^{3 ′} represents a linear alkylene group having 2 to 4 carbon atoms, and R ¹¹ , R ¹² and R ¹³ are each independently a linear alkyl group having 1 to 4 carbon atoms. R ²² represents a linear alkyl group having 1 to 6 carbon atoms, and X ⁻ represents a halide ion selected from a chloride ion, a bromide ion, and an iodide ion. The catalyst according to claim 5, which is obtained by reacting a silicon compound and silica. A catalyst containing silica surface-modified with the quaternary ammonium ionic group is represented by the formula (17):

The catalyst according to claim 5, which is obtained by reacting a silicon-containing compound represented by formula (II) with silica. The epoxide represented by the general formula (1) is represented by the general formula (18).

(Wherein R ^{1 ′} represents a hydrogen atom or a methyl group), and the cyclic sulfite represented by the general formula (2) is represented by the general formula (19)

The catalyst according to claim 5, wherein R ^{1 ′} is the same as defined above.

Images