Method for producing organosilicon compounds having (meth)acryloxy groups

Abstract

To provide a method for producing an organosilicon compound having a (meth)acryloxy group, which can suppress a reaction in which a (meth) acrylate compound, which is a raw material, self-polymerizes when producing an organosilicon compound having a (meth)acryloyloxy group on an industrial scale and the like.SOLUTION: There is provided a method for producing an organosilicon compound of the general formula (3) by subjecting a hydrosilane compound represented by the general formula (1) (R1 is a hydrocarbon group having 1 to 10 carbon atoms and X is a halogen atom) and a (meth)acrylate compound having an alkenyl group represented by the general formula (2) (R2 is H or a methyl group and R3 is a divalent hydrocarbon group having 1 to 18 carbon atoms) to hydrosilylation reaction using a platinum catalyst in the presence of an acid amide compound.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a method for producing an organosilicon compound having a (meth)acryloxy group. [Background technology]

[0002] In an organosilicon compound having a hydrolyzable silyl group and an organic group, a silanol group generated by hydrolysis of the hydrolyzable silyl group forms a covalent bond with a hydroxyl group on the surface of an inorganic material, and the organic group further reacts with the organic material, thereby making it possible to bond an organic material and an inorganic material that are normally difficult to bond together. This makes it possible to impart properties such as heat resistance, water resistance, weather resistance, improved mechanical strength, adhesion, dispersibility, hydrophobicity, and rust resistance to the organic-inorganic composite material. Taking advantage of these properties, the above organosilicon compounds are used in a wide range of fields and applications, such as silane coupling agents, resin additives, surface treatment agents, fiber treatment agents, adhesives, paint additives, and polymer modifiers.

[0003] Among the above-mentioned organosilicon compounds, organosilicon compounds having an acryloyloxy group or a methacryloyloxy group (hereinafter, both are collectively referred to as "(meth)acryloyloxy group") are useful compounds as radical polymerizable monomers for obtaining silicon-containing polymers, since the (meth)acryloyloxy group, which is a polymerizable functional group, copolymerizes with various radical polymerizable monomers. Examples of such organosilicon compounds having a (meth)acryloyloxy group include 3-acryloyloxypropyltrichlorosilane and 3-methacryloyloxypropyltrichlorosilane (Patent Document 1).

[0004] The organosilicon compound having the above-mentioned (meth)acryloyloxy group is generally synthesized by subjecting a hydrohalosilane compound and an acrylate compound or methacrylate compound having an alkenyl group (hereinafter, both are collectively referred to as "(meth)acrylate compound") to a hydrosilylation reaction in the presence of a platinum catalyst. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Japanese Patent Application Publication No. 11-29583 Summary of the Invention [Problem to be solved by the invention]

[0006] However, the organosilicon compound having a (meth)acryloyloxy group described in Patent Document 1 is prone to self-polymerization of its characteristic polymerizable functional group, and various problems arise when it is produced on an industrial scale. Specifically, the polymerizable functional group reacts with a radical species generated by heat during production to form a new radical species (initiation reaction). The reaction between the polymerizable functional group and the radical species is an exothermic reaction, and when the temperature rises due to the reaction, another polymerizable functional group reacts with the new radical species in a chain and accelerated manner, resulting in self-polymerization (growth reaction). When the temperature rises rapidly due to self-polymerization and it becomes impossible to control the reaction, the reaction liquid vaporizes or pyrolyzes, etc., generating flammable gases, and in the worst case, there is a risk of causing accidents such as fires and explosions (runaway reaction). In addition, there is also a problem that the polymerized product clogs the inside of the equipment or piping, causing great damage to the production process. For these reasons, in order to easily produce the above organosilicon compounds on an industrial scale, it is extremely important to establish a method for suppressing self-polymerization.

[0007] The reactivity of a radical polymerizable monomer with a radical species is greatly affected by the structure of the radical polymerizable monomer. In the production of the above-mentioned organosilicon compound having a (meth)acryloyloxy group, the raw material (meth)acrylate compound and the product organosilicon compound having a (meth)acryloyloxy group have (meth)acryloyloxy groups with extremely large propagation rate constants of radical species, and the initiation reaction proceeds rapidly. However, in the product, an organosilicon compound having a (meth)acryloyloxy group, the radical species is stabilized by the substituent effect of the silyl group, which has a large steric hindrance, so the propagation reaction is slow and it does not directly cause self-polymerization.On the other hand, in the raw material (meth)acrylate compound, the steric hindrance of the alkenyl group is small, so the propagation reaction proceeds quickly, and it directly causes self-polymerization. For the above reasons, in order to easily produce organosilicon compounds having (meth)acryloyloxy groups on an industrial scale, it is extremely important to establish a method for suppressing the self-polymerization of polymerizable functional groups. Specifically, it is extremely important to establish a method for suppressing the propagation reaction of the raw material (meth)acrylate compound.

[0008] As a method for suppressing the self-polymerization of the polymerizable functional group, the addition of various polymerization inhibitors is known. Among the polymerization inhibitors, for example, phenol-based polymerization inhibitors are known as those capable of suppressing the growth reaction of the raw material (meth)acrylate compound. For example, phenol-based polymerization inhibitors, hindered phenol-based polymerization inhibitors, etc. are known as those capable of suppressing the growth reaction of the product (meth)acryloyloxy group-containing organosilicon compound. In the production of organosilicon compounds having (meth)acryloyloxy groups, phenol-based polymerization inhibitors such as 4-methoxyphenol having a hydroxyl group have the highest reactivity with radical species in the reaction system, and therefore can suppress both the initiation reaction and the propagation reaction by quickly capturing the generated radical species. However, in the presence of a halosilane compound, the hydroxyl group gradually reacts with the halosilane compound, causing the hydroxyl group to lose its radical capturing ability, and it no longer acts as a polymerization inhibitor. In the case of a hindered phenol-based polymerization inhibitor such as 2,6-di-tert-butyl-4-methylphenol having a substituent with large steric hindrance around the hydroxyl group, the hydroxyl group hardly reacts with the halosilane compound due to the influence of the substituent with large steric hindrance. However, this hindered phenol-based polymerization inhibitor has a moderate reactivity with radical species, so it cannot quickly capture the generated radical species and cannot suppress the initiation reaction. In addition, once the initiation reaction begins, the radical species react in a chain and accelerated manner. At this time, the reactivity of the hindered phenol-based polymerization inhibitor with the radical species is higher than the reactivity of the product organosilicon compound with the radical species, but is lower than the reactivity of the raw material (meth)acrylate compound with the radical species, so it cannot suppress the growth reaction of the raw material (meth)acrylate compound. For the reasons described above, the above-mentioned various polymerization inhibitors were insufficient in their effect of suppressing the propagation reaction of the raw material (meth)acrylate compound in the presence of a halosilane compound.

[0009] Therefore, when producing an organosilicon compound having a (meth)acryloyloxy group on an industrial scale, it has been desired to develop a method capable of suppressing the propagation reaction of the raw material (meth)acrylate compound.

[0010] The present invention has been made in view of the above circumstances, and has an object to provide a method for producing an organosilicon compound having a (meth)acryloyloxy group, which can suppress the propagation reaction in which the raw material (meth)acrylate compound self-polymerizes when producing an organosilicon compound having a (meth)acryloyloxy group on an industrial scale or the like. [Means for solving the problem]

[0011] Means for Solving the Problems The present inventors have conducted extensive research in order to achieve the above-mentioned object, and as a result have discovered that the propagation reaction of the raw material (meth)acrylate compound can be suppressed by subjecting a hydrohalosilane compound and a (meth)acrylate compound having an alkenyl group to a hydrosilylation reaction in the presence of an acid amide compound using a platinum catalyst, thereby completing the present invention.

[0012] That is, the present invention provides 1. The following general formula (1) [ka] (In the formula, R 1 represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, X represents a halogen atom, and n represents an integer of 1 to 3. and a hydrohalosilane compound represented by the following general formula (2): [ka] (In the formula, R 2 represents a hydrogen atom or a methyl group, and R 3 represents an unsubstituted divalent hydrocarbon group having 1 to 18 carbon atoms. and a (meth)acrylate compound having an alkenyl group represented by the following general formula (3): [ka] (In the formula, R 1 , R 2 , R 3 , X and n have the same meanings as above. A method for producing an organosilicon compound having an acryloxy group or a methacryloxy group, 2. The acid amide compound is represented by the following general formula (4): [ka] (In the formula, R 4 represents a hydrogen atom or a substituted or unsubstituted k-valent hydrocarbon group having 1 to 30 carbon atoms; R 5 each independently represents a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 30 carbon atoms, and k represents an integer of 1 or 2. or an acid amide compound represented by the following general formula (5): [ka] (In the formula, R 6 represents a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 30 carbon atoms. A method for producing an organosilicon compound having an acryloxy group or a methacryloxy group, which is a primary acid amide compound represented by the formula (1): 3. A method for producing an organosilicon compound having one or two acryloxy or methacryloxy groups, wherein the acid amide compound is one or more selected from the group consisting of acetamide, N-methylacetamide, N,N-dimethylacetamide, malonamide, succinamide, maleamide, fumaramide, benzamide, propionamide, butyramide, palmitamide, stearamide, oleamide, and erucamide; 4. A method for producing an organosilicon compound having an acryloxy group or a methacryloxy group according to any one of 1 to 3, wherein the hydrosilylation reaction is carried out in the presence of a polymerization inhibitor. 5. The method for producing an organosilicon compound having an acryloxy group or a methacryloxy group according to 4, wherein the polymerization inhibitor is a phenol-based polymerization inhibitor or a hindered phenol-based polymerization inhibitor. 6. A method for producing an organosilicon compound having an acryloxy group or a methacryloxy group as described in 5, wherein the phenol-based polymerization inhibitor is one or more selected from the group consisting of 4-methoxyphenol, 2-methyl-4-methoxyphenol, 2-tert-butyl-4-methoxyphenol, and 4-hydroxyphenol. 7. The method for producing an organosilicon compound having an acryloxy group or methacryloxy group according to claim 5, wherein the hindered phenol-based polymerization inhibitor is one or more selected from the group consisting of 2,6-di-tert-butyl-4-methylphenol, 4,4-methylenebis(2,6-di-tert-butylphenol), 2,2-methylenebis(6-tert-butyl-4-methylphenol), 2,6-di-tert-butyl-4-dimethylaminomethylphenol, 2,6-di-tert-butyl-4-methoxyphenol, 2,6-di-tert-butyl-4-hydroxyphenol, and 3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-2H-1-benzopyran-6-ol. to provide. Effect of the Invention

[0013] According to the production method of the present invention, the use of an acid amide compound can suppress the propagation reaction of the raw material (meth)acrylate compound in the presence of a hydrohalosilane compound. Furthermore, when a hydrosilylation reaction is carried out in the presence of a polymerization inhibitor, the mutual effect of the acid amide compound and the polymerization inhibitor can enhance the effect compared to the use of each compound alone. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0014] The present invention will be specifically described below. In the present invention, a hydrohalosilane compound represented by the following general formula (1) (hereinafter referred to as "compound (1)") and a (meth)acrylate compound having an alkenyl group represented by the following general formula (2) (hereinafter referred to as "compound (2)") are subjected to a hydrosilylation reaction using a platinum catalyst in the presence of an acid amide compound to produce an organosilicon compound having a (meth)acryloxy group represented by the general formula (3) (hereinafter referred to as "compound (3)").

[0015] [ka]

[0016] In the above general formula (1), R 1 represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms, and even more preferably 1 or 2 carbon atoms. The monovalent hydrocarbon group may be linear, branched or cyclic, and specific examples thereof include linear alkyl groups such as methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl and n-decyl groups; branched alkyl groups such as sec-propyl, sec-butyl, tert-butyl, sec-pentyl, tert-pentyl, sec-hexyl, tert-hexyl, sec-heptyl, tert-heptyl, sec-octyl, tert-octyl, sec-nonyl, tert-nonyl, sec-decyl and tert-decyl groups; cyclic alkyl groups such as cyclopentyl and cyclohexyl groups; alkenyl groups such as vinyl, allyl, butenyl and methallyl groups; aryl groups such as phenyl, tolyl and xylyl groups; and aralkyl groups such as benzyl and phenethyl groups. Among these, R 1 As the alkyl group, an unsubstituted linear alkyl group having 1 to 3 carbon atoms is preferable, and from the viewpoint of availability in particular, a methyl group or an ethyl group is more preferable.

[0017] In addition, some or all of the hydrogen atoms of these monovalent hydrocarbon groups may be substituted with other substituents, and specific examples of the substituents include alkoxy groups having 1 to 3 carbon atoms such as methoxy, ethoxy, and (iso)propoxy groups; halogen atoms such as fluorine, chlorine, and bromine; aromatic hydrocarbon groups such as phenyl groups; cyano groups, amino groups, ester groups, ether groups, carbonyl groups, acyl groups, and sulfide groups, and one or more of these substituents may be used in combination. The substitution positions of these substituents are not particularly limited, and the number of substituents is also not limited.

[0018] In the above general formula (1), X represents a halogen atom. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. From the viewpoint of availability, a chlorine atom and a bromine atom are preferred. Furthermore, n is an integer of 1 to 3, and is preferably 2 or 3 from the viewpoint of increasing adhesion by reacting with multiple hydroxyl groups on the surface of a substrate, particularly when used as a silane coupling agent.

[0019] Specific examples of compound (1) include fluorosilane compounds such as trifluorosilane, difluoromethylsilane, fluorodimethylsilane, difluoroethylsilane, fluorodiethylsilane, difluoropropylsilane, fluorodipropylsilane, difluorophenylsilane, and fluorodiphenylsilane; chlorosilane compounds such as trichlorosilane, dichloromethylsilane, chlorodimethylsilane, dichloroethylsilane, chlorodiethylsilane, dichloropropylsilane, chlorodipropylsilane, dichlorophenylsilane, and chlorodiphenylsilane; Bromosilane compounds such as tribromosilane, dibromomethylsilane, bromodimethylsilane, dibromoethylsilane, bromodiethylsilane, dibromopropylsilane, bromodipropylsilane, dibromophenylsilane, and bromodiphenylsilane; Examples of the iodosilane include iodosilane compounds such as triiodosilane, diiodomethylsilane, iododimethylsilane, diiodoethylsilane, iododiethylsilane, diiodopropylsilane, iododipropylsilane, diiodophenylsilane, and iododiphenylsilane. Among these, trichlorosilane, dichloromethylsilane, chlorodimethylsilane, dichloroethylsilane, and chlorodiethylsilane are preferred from the viewpoint of availability.

[0020] In the above general formula (2), R 2 represents a hydrogen atom or a methyl group, and R 3 represents an unsubstituted divalent hydrocarbon group having 1 to 18 carbon atoms, preferably 1 to 14 carbon atoms, more preferably 1 to 8 carbon atoms, and even more preferably 1 to 6 carbon atoms.

[0021] The divalent hydrocarbon group may be linear, branched or cyclic, and specific examples thereof include linear alkylene groups such as methylene, ethylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, heptamethylene, octamethylene, nonamethylene, decylene, undecylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecylene and octadecylene; sec-propylene, sec-butylene, tert-butylene, sec-pentylene, tert-pentylene, sec-hexylene, tert-hexylene, sec-heptylene, tert-heptylene, sec-octylene and tert-octylene; branched alkylene groups such as octylene, sec-nonylene, tert-nonylene, sec-decylene, tert-decylene, sec-undecylene, tert-undecylene, sec-dodecylene, tert-dodecylene, sec-tridecylene, tert-tridecylene, sec-tetradecylene, tert-tetradecylene, sec-pentadecylene, tert-pentadecylene, sec-hexadecylene, tert-hexadecylene, sec-heptadecylene, tert-heptadecylene, sec-octadecylene, and tert-octadecylene; and cyclic alkylene groups such as cyclopropylene, cyclopentylene, and cyclohexylene. Among these, R 2 As the alkyl group, an unsubstituted linear alkylene group having 1 to 8 carbon atoms is preferable, and from the viewpoint of easy availability, an unsubstituted linear alkylene group having 1 to 6 carbon atoms such as a methylene group or an ethylene group is more preferable.

[0022] Specific examples of the compound (2) include allyl (meth)acrylate, 3-butenyl (meth)acrylate, 4-pentenyl (meth)acrylate, 5-hexenyl (meth)acrylate, 6-heptenyl (meth)acrylate, 7-octenyl (meth)acrylate, 8-nonenyl (meth)acrylate, 9-decenyl (meth)acrylate, 10-undecenyl (meth)acrylate, and 11-dodecenyl (meth)acrylate. and (meth)acrylate compounds such as 12-tridecenyl (meth)acrylate, 13-tetradecenyl (meth)acrylate, 14-pentadecenyl (meth)acrylate, 15-hexadecenyl (meth)acrylate, 16-heptadecenyl (meth)acrylate, 17-octadecenyl (meth)acrylate, 18-nonadecenyl (meth)acrylate, and 19-icosenyl (meth)acrylate. Among these, allyl (meth)acrylate, 3-butenyl (meth)acrylate, 4-pentenyl (meth)acrylate, 5-hexenyl (meth)acrylate, 6-heptenyl (meth)acrylate, and 7-octenyl (meth)acrylate are preferred, particularly from the viewpoint of availability.

[0023] In the above general formula (3), R 1 , R 2 , R 3 , X and n are the same as in general formula (1) and general formula (2).

[0024] Specific examples of the compound (3) include 3-(meth)acryloxypropyltrifluorosilane, 3-(meth)acryloxypropyldifluoromethylsilane, 3-(meth)acryloxypropylfluorodimethylsilane, 4-(meth)acryloxybutyltrifluorosilane, 4-(meth)acryloxybutyldifluoromethylsilane, 4-(meth)acryloxybutylfluorodimethylsilane, 5-(meth)acryloxypentyltrifluorosilane, 5-(meth)acryloxypentyldifluoromethylsilane, 5-(meth)acryloxypentyldifluoromethylsilane, and 5-(meth)acryloxypentylfluorodimethylsilane. ethylfluorodimethylsilane, 6-(meth)acryloxyhexyltrifluorosilane, 6-(meth)acryloxyhexyldifluoromethylsilane, 6-(meth)acryloxyhexylfluorodimethylsilane, 7-(meth)acryloxyheptyltrifluorosilane, 7-(meth)acryloxyheptyldifluoromethylsilane, 7-acryloxyheptylfluorodimethylsilane, 8-(meth)acryloxyoctyltrifluorosilane, 8-(meth)acryloxyoctyldifluoromethylsilane, 8-(meth)acryloxyoctylfluoro dimethylsilane, 9-(meth)acryloxynonyltrifluorosilane, 9-(meth)acryloxynonyldifluoromethylsilane, 9-(meth)acryloxynonylfluorodimethylsilane, 10-(meth)acryloxydecyltrifluorosilane, 10-(meth)acryloxydecyldifluoromethylsilane, 10-(meth)acryloxydecylfluorodimethylsilane, 11-(meth)acryloxyundecyltrifluorosilane, 11-(meth)acryloxyundecyldifluoromethylsilane, 11-(meth)acryloxyundecyl fluorodimethylsilane, 12-(meth)acryloxydodecyltrifluorosilane, 12-(meth)acryloxydodecyldifluoromethylsilane, 12-(meth)acryloxydodecylfluorodimethylsilane, 13-(meth)acryloxytridecyltrifluorosilane, 13-(meth)acryloxytridecyldifluoromethylsilane, 13-(meth)acryloxytridecylfluorodimethylsilane, 14-(meth)acryloxytetradecyltrifluorosilane, 14-(meth)acryloxytetradecyldifluoromethylsilane,14-(meth)acryloxytetradecylfluorodimethylsilane, 15-(meth)acryloxypentadecyltrifluorosilane, 15-(meth)acryloxypentadecyldifluoromethylsilane, 15-(meth)acryloxypentadecylfluorodimethylsilane, 16-(meth)acryloxyhexadecyltrifluorosilane, 16-(meth)acryloxyhexadecyldifluoromethylsilane, 16-(meth)acryloxyhexadecylfluorodimethylsilane, 17 ... 17-(meth)acryloxyheptadecyltrifluorosilane, 17-(meth)acryloxyheptadecyldifluoromethylsilane, 17-(meth)acryloxyheptadecylfluorodimethylsilane, 18-(meth)acryloxyoctadecyltrifluorosilane, 18-(meth)acryloxyoctadecyldifluoromethylsilane, 18-(meth)acryloxyoctadecylfluorodimethylsilane, 19-(meth)acryloxynonadecyltrifluorosilane, 19-(meth)acryloxynonadecyldifluoromethylsilane Fluorosilane compounds such as ethylsilane, 19-(meth)acryloxynonadecylfluorodimethylsilane, 20-(meth)acryloxyicosyltrifluorosilane, 20-(meth)acryloxyicosyldifluoromethylsilane, 20-(meth)acryloxyicosylfluorodimethylsilane, 3-(meth)methacryloxypropyltrifluorosilane, and 3-(meth)methacryloxypropyldifluoromethylsilane; 3-(meth)acryloxypropyltrichlorosilane, 3-(meth)acryloyloxypropyldifluoromethylsilane, and the like. dimethylsilane, 3-(meth)acryloxypropyl chlorodimethylsilane, 4-(meth)acryloxybutyl trichlorosilane, 4-(meth)acryloxybutyl dichloromethylsilane, 4-(meth)acryloxybutyl chlorodimethylsilane, 5-(meth)acryloxypentyl trichlorosilane, 5-(meth)acryloxypentyl dichloromethylsilane, 5-(meth)acryloxypentyl chlorodimethylsilane, 6-(meth)acryloxyhexyl trichlorosilane, 6-(meth)acryloxyhexyl dichloromethylsilane, 6-(meth)acryloxyhexyl chlorodimethylsilane, 7-(meth)acryloxyheptyl trichlorosilane, 7-(meth)acryloxyheptyl dichloromethylsilane, 7-(meth)acryloxyheptyl chlorodimethylsilane, 8-(meth)acryloxyoctyl trichlorosilane, 8-(meth)acryloxyoctyl dichloromethylsilane, 8-(meth)acryloxyoctyl chlorodimethylsilane, 9-(meth)acryloxynonyl trichlorosilane, 9-(meth)acryloxy Nonyldichloromethylsilane, 9-(meth)acryloxynonylchlorodimethylsilane, 10-(meth)acryloxydecyltrichlorosilane, 10-(meth)acryloxydecyldichloromethylsilane, 10-acryloxydecylchlorodimethylsilane, 11-(meth)acryloxyundecyltrichlorosilane, 11-(meth)acryloxyundecyldichloromethylsilane, 11-(meth)acryloxyundecylchlorodimethylsilane, 12-(meth)acryloxydodecyltrichlorosilane, 12-(meth)acryloxydodecyldichloromethylsilane Lusilane, 12-(meth)acryloxydodecylchlorodimethylsilane, 13-(meth)acryloxytridecyltrichlorosilane, 13-(meth)acryloxytridecyldichloromethylsilane, 13-(meth)acryloxytridecylchlorodimethylsilane, 14-(meth)acryloxytetradecyltrichlorosilane, 14-(meth)acryloxytetradecyldichloromethylsilane, 14-(meth)acryloxytetradecylchlorodimethylsilane, 15-(meth)acryloxypentadecyltrichlorosilane, 15-(meth)acryloxypentadecyltrichlorosilane, 15-(meth)acryloxypentadecyltrichlorosilane Tadecyldichloromethylsilane, 15-(meth)acryloxypentadecylchlorodimethylsilane, 16-(meth)acryloxyhexadecyltrichlorosilane, 16-(meth)acryloxyhexadecyldichloromethylsilane, 16-(meth)acryloxyhexadecylchlorodimethylsilane, 17-(meth)acryloxyheptadecyltrichlorosilane, 17-(meth)acryloxyheptadecyldichloromethylsilane, 17-(meth)acryloxyheptadecylchlorodimethylsilane, 18-(meth)acryloxyoctadecyltrichlorosilane,18-(meth)acryloxyoctadecyldichloromethylsilane, 18-(meth)acryloxyoctadecylchlorodimethylsilane, 19-(meth)acryloxynonadecyltrichlorosilane, 19-(meth)acryloxynonadecyldichloromethylsilane, 19-(meth)acryloxynonadecylchlorodimethylsilane, 20-(meth)acryloxyicosyltrichlorosilane, 20-(meth)acryloxyicosyldichloromethylsilane, 20-(meth)acryloxyicosylchlorodimethylsilane chlorosilane compounds such as silane; 3-(meth)acryloxypropyltribromosilane, 3-(meth)acryloxypropyldibromomethylsilane, 3-(meth)acryloxypropylbromodimethylsilane, 4-(meth)acryloxybutyltribromosilane, 4-(meth)acryloxybutyldibromomethylsilane, 4-(meth)acryloxybutylbromodimethylsilane, 5-(meth)acryloxypentyltribromosilane, 5-(meth)acryloxypentyldibromomethylsilane, 5-(meth)acryloxypentylbromodimethylsilane, 6-(meth)acryloxyhexyltribromosilane, 6-(meth)acryloxyhexyldibromomethylsilane, 6-(meth)acryloxyhexylbromodimethylsilane, 7-(meth)acryloxyheptyltribromosilane, 7-(meth)acryloxyheptyldibromomethylsilane, 7-(meth)acryloxyheptylbromodimethylsilane, 8-(meth)acryloxyoctyltribromosilane, 8-(meth)acryloxyoctyldibromomethylsilane, 8-(meth)acrylo 9-(meth)acryloxynonyltribromosilane, 9-(meth)acryloxynonyldibromomethylsilane, 9-(meth)acryloxynonylbromodimethylsilane, 10-(meth)acryloxydecyltribromosilane, 10-(meth)acryloxydecyldibromomethylsilane, 10-(meth)acryloxydecylbromodimethylsilane, 11-(meth)acryloxyundecyltribromosilane, 11-(meth)acryloxyundecyldibromomethylsilane, 11-(meth)acryloxyundecylbromodimethylsilane Bromodimethylsilane, 12-(meth)acryloxydodecyltribromosilane, 12-(meth)acryloxydodecyldibromomethylsilane, 12-(meth)acryloxydodecylbromodimethylsilane, 13-(meth)acryloxytridecyltribromosilane, 13-(meth)acryloxytridecyldibromomethylsilane, 13-(meth)acryloxytridecylbromodimethylsilane, 14-(meth)acryloxytetradecyltribromosilane, 14-(meth)acryloxytetradecyldibromomethylsilane, 14-(meth)acryloxytetradecyldibromomethylsilane, cytetradecylbromodimethylsilane, 15-(meth)acryloxypentadecyltribromosilane, 15-acryloxypentadecyldibromomethylsilane, 15-(meth)acryloxypentadecylbromodimethylsilane, 16-(meth)acryloxyhexadecyltribromosilane, 16-(meth)acryloxyhexadecyldibromomethylsilane, 16-(meth)acryloxyhexadecylbromodimethylsilane, 17-(meth)acryloxyheptadecyltribromosilane, 17-(meth)acryloxyheptadecyldibromomethylsilane,17-(meth)acryloxyheptadecylbromodimethylsilane, 18-(meth)acryloxyoctadecyltribromosilane, 18-(meth)acryloxyoctadecyldibromomethylsilane, 18-(meth)acryloxyoctadecylbromodimethylsilane, 19-(meth)acryloxynonadecyltribromosilane, 19-(meth)acryloxynonadecyldibromomethylsilane, 19-(meth)acryloxynonadecylbromodimethylsilane, 20-(meth)acryloxyicosyltribromo Silane, bromosilane compounds such as 20-(meth)acryloxyicosyldibromomethylsilane and 20-(meth)acryloxyicosylbromodimethylsilane; 3-(meth)acryloxypropyltriiodosilane, 3-(meth)acryloxypropyldiiodomethylsilane, 3-(meth)acryloxypropyliododimethylsilane, 4-(meth)acryloxybutyltriiodosilane, 4-(meth)acryloxybutyldiiodomethylsilane, 4-(meth)acryloxybutyliododimethylsilane, 5-(meth)acryloxypentyl triiodosilane, 5-(meth)acryloxypentyl diiodomethylsilane, 5-(meth)acryloxypentyl iododimethylsilane, 6-(meth)acryloxyhexyl triiodosilane, 6-(meth)acryloxyhexyl diiodomethylsilane, 6-(meth)acryloxyhexyl iododimethylsilane, 7-(meth)acryloxyheptyl triiodosilane, 7-(meth)acryloxyheptyl diiodomethylsilane, 7-(meth)acryloxyheptyl iododimethylsilane, 8-(meth)acryloxyheptyl , 8-(meth)acryloxyoctyldiiodomethylsilane, 8-(meth)acryloxyoctyliododimethylsilane, 9-(meth)acryloxynonyltriiodosilane, 9-(meth)acryloxynonyldiiodomethylsilane, 9-(meth)acryloxynonyliododimethylsilane, 10-(meth)acryloxydecyltriiodosilane, 10-(meth)acryloxydecyldiiodomethylsilane, 10-(meth)acryloxydecyldiiododimethylsilane, 11-(meth)acryloxyundecyltriiodosilane Dosilane, 11-(meth)acryloxyundecyldiiodomethylsilane, 11-(meth)acryloxyundecyliododimethylsilane, 12-(meth)acryloxydodecyltriiodosilane, 12-(meth)acryloxydodecyldiiodomethylsilane, 12-(meth)acryloxydodecyldiiododimethylsilane, 13-(meth)acryloxytridecyltriiodosilane, 13-(meth)acryloxytridecyldiiodomethylsilane, 13-(meth)acryloxytridecyldiiododimethylsilane, 14-(meth)acryloxytetradecyl Siltriiodosilane, 14-(meth)acryloxytetradecyldiiodomethylsilane, 14-(meth)acryloxytetradecyliododimethylsilane, 15-(meth)acryloxypentadecyltriiodosilane, 15-(meth)acryloxypentadecyldiiodomethylsilane, 15-(meth)acryloxypentadecyliododimethylsilane, 16-(meth)acryloxyhexadecyltriiodosilane, 16-(meth)acryloxyhexadecyldiiodomethylsilane, 16-(meth)acryloxyhexadecyliododimethylsilane,17-(meth)acryloxyheptadecyltriiodosilane, 17-(meth)acryloxyheptadecyldiiodomethylsilane, 17-acryloxyheptadecyliododimethylsilane, 18-(meth)acryloxyoctadecyltriiodosilane, 18-(meth)acryloxyoctadecyldiiodomethylsilane, 18-(meth)acryloxyoctadecyliododimethylsilane, 19-(meth)acryloxyoctadecyltriiodosilane, ) iodosilane compounds such as acryloxynonadecyltriiodosilane, 19-(meth)acryloxynonadecyldiiodomethylsilane, 19-(meth)acryloxynonadecyliododimethylsilane, 20-(meth)acryloxyicosyltriiodosilane, 20-(meth)acryloxyicosyldiiodomethylsilane, and 20-(meth)acryloxyicosyliododimethylsilane.

[0025] Among these, particularly from the viewpoint of the ease of availability of precursor raw materials, 3-(meth)acryloxypropyltrichlorosilane, 3-(meth)acryloxypropyldichloromethylsilane, 3-(meth)acryloxypropylchlorodimethylsilane, 4-(meth)acryloxybutyltrichlorosilane, 4-(meth)acryloxybutyldichloromethylsilane, 4-(meth)acryloxybutylchlorodimethylsilane, 5-(meth)acryloxypentyltrichlorosilane, 5-(meth)acryloxypentyldichloromethylsilane, 5-(meth)acryloxypentylchlorodimethylsilane, 5-(meth)acryloxypentyltrichlorosilane, 5-(meth)acryloxypentyldichloromethylsilane, 5-(meth)acryloxypentylchlorodimethylsilane, 5-(meth)acryloxypentylchlorodimethylsilane, 5-(meth)acryloxypentylchlorodimethylsilane, 5-(meth)acryloxypentylchlorodimethylsilane, 5-(meth)acryloxypentylchlorodimethylsilane, 5-(meth)acryloxypentylchlorodimethylsilane, 5-(meth)acryloxypentylchloromethyl ... Preferred are 6-(meth)acryloxyhexyltrichlorosilane, 6-(meth)acryloxyhexyldichloromethylsilane, 6-(meth)acryloxyhexylchlorodimethylsilane, 7-(meth)acryloxyheptyltrichlorosilane, 7-(meth)acryloxyheptyldichloromethylsilane, 7-(meth)acryloxyheptylchlorodimethylsilane, 8-(meth)acryloxyoctyltrichlorosilane, 8-(meth)acryloxyoctyldichloromethylsilane, and 8-(meth)acryloxyoctylchlorodimethylsilane.

[0026] In the production method of the present invention, the mixing ratio of compound (1) and compound (2) is not particularly limited, but from the viewpoints of reactivity and productivity, it is preferably in the range of 1 to 20 moles, more preferably 1 to 10 moles, and even more preferably 1 to 5 moles of compound (1) per mole of compound (2).

[0027] The method for confirming the contents of the compounds (1) to (3) in the reaction system is not particularly limited, and analytical means such as gas chromatography, high performance liquid chromatography, thin layer chromatography, nuclear magnetic resonance spectroscopy (NMR), infrared spectroscopy (IR), and near infrared spectroscopy (NIR) can be used.

[0028] In the present invention, the hydrosilylation reaction is carried out in the presence of an acid amide compound, thereby making it possible to suppress the propagation reaction of the raw material (meth)acrylate compound. As the acid amide compound, for example, an acid amide compound represented by the following general formula (4) (hereinafter referred to as "compound (4)") or a primary acid amide compound represented by the following general formula (5) (hereinafter referred to as "compound (5)") is preferable.

[0029] [ka]

[0030] In the above general formula (4), R 4 represents a hydrogen atom or an unsubstituted k-valent hydrocarbon group having 1 to 30 carbon atoms, preferably 1 to 25 carbon atoms, more preferably 1 to 20 carbon atoms, and even more preferably 1 to 10 carbon atoms, where k represents an integer of 1 or 2.

[0031] When k is 1, the monovalent hydrocarbon group may be linear, branched or cyclic, and specific examples thereof include linear alkyl groups such as methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl and n-decyl groups; branched alkyl groups such as sec-propyl, sec-butyl, tert-butyl, sec-pentyl, tert-pentyl, sec-hexyl, tert-hexyl, sec-heptyl, tert-heptyl, sec-octyl, tert-octyl, sec-nonyl, tert-nonyl, sec-decyl and tert-decyl groups; cyclic alkyl groups such as cyclopentyl and cyclohexyl groups; alkenyl groups such as vinyl, allyl, butenyl and methallyl groups; aryl groups such as phenyl, tolyl and xylyl groups; and aralkyl groups such as benzyl and phenethyl groups.

[0032] When k is 2, the divalent hydrocarbon group may be linear, branched or cyclic. Specific examples thereof include linear alkylene groups such as methylene, ethylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, heptamethylene, octamethylene, nonamethylene, decylene, undecylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecylene and octadecylene; sec-propylene, sec-butylene, tert-butylene, sec-pentylene, tert-pentylene, sec-hexylene, tert-hexylene, sec-heptylene, tert-heptylene, sec-octylene and tert-hexylene. branched alkylene groups such as sec-octylene, sec-nonylene, tert-nonylene, sec-decylene, tert-decylene, sec-undecylene, tert-undecylene, sec-dodecylene, tert-dodecylene, sec-tridecylene, tert-tridecylene, sec-tetradecylene, tert-tetradecylene, sec-pentadecylene, tert-pentadecylene, sec-hexadecylene, tert-hexadecylene, sec-heptadecylene, tert-heptadecylene, sec-octadecylene, and tert-octadecylene groups; and cyclic alkylene groups such as cyclopropylene, cyclopentylene, and cyclohexylene groups.

[0033] Among these, R 4 As the alkyl group, a hydrogen atom, a linear alkyl group having 1 to 20 carbon atoms, or a linear alkenyl group having 2 to 20 carbon atoms is preferable, and from the viewpoint of easy availability, a hydrogen atom, a linear alkyl group having 1 to 10 carbon atoms, or a linear alkenyl group having 2 to 10 carbon atoms is more preferable.

[0034] Some or all of the hydrogen atoms of these monovalent and divalent hydrocarbon groups may be substituted with other substituents. Specific examples of such substituents include R 1 is the same as the substituent with which some or all of the hydrogen atoms of the monovalent hydrocarbon group may be substituted.

[0035] In the above general formula (4), R 5 each independently represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 30 carbon atoms, preferably 1 to 25 carbon atoms, more preferably 1 to 20 carbon atoms, and even more preferably 1 to 10 carbon atoms. As the monovalent hydrocarbon group, R 4 The same substituents as those mentioned above can be mentioned. Among these, R 5 As the alkyl group, a hydrogen atom, a linear alkyl group having 1 to 20 carbon atoms, or a linear alkenyl group having 2 to 10 carbon atoms is preferable, and from the viewpoint of easy availability, a hydrogen atom, a linear alkyl group having 1 to 10 carbon atoms, or a linear alkenyl group having 2 to 10 carbon atoms is more preferable.

[0036] Specific examples of compound (4) include N-methylacetamide, N,N-dimethylacetamide, malonamide, succinamide, maleamide, fumaramide, phthalamide, isophthalamide, terephthalamide, N-methylformamide, N,N-dimethylformamide, octanediamide, oxamide, glutaramide, and adipamide.

[0037] In the above general formula (5), R 6represents a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 30 carbon atoms, preferably 1 to 25 carbon atoms, more preferably 1 to 20 carbon atoms, and even more preferably 1 to 10 carbon atoms. As the monovalent hydrocarbon group, R 4 The same substituents as those mentioned above can be mentioned. Among these, R 6 As the alkyl group, a hydrogen atom, a linear alkyl group having 1 to 20 carbon atoms, or a linear alkenyl group having 2 to 10 carbon atoms is preferable, and from the viewpoint of easy availability, a hydrogen atom, a linear alkyl group having 1 to 10 carbon atoms, or a linear alkenyl group having 2 to 10 carbon atoms is more preferable.

[0038] Some or all of the hydrogen atoms of these monovalent and divalent hydrocarbon groups may be substituted with other substituents. Specific examples of such substituents include R 1 is the same as the substituent with which some or all of the hydrogen atoms of the monovalent hydrocarbon group may be substituted.

[0039] Specific examples of compound (5) include acetamide, acrylamide, benzamide, 2-naphthamide, nicotinamide, isonicotinamide, 2-furamide, formamide, propionamide, propiolamide, butyramide, isobutyramide, hexanamide, cyclohexanecarboxamide, methacrylamide, palmitamide, stearamide, oleamide, erucamide, and cinnamamide. These are commercially available as reagents, and from the viewpoints of easy availability and auxiliary effect, acetamide, N-methylacetamide, N,N-dimethylacetamide, malonamide, succinamide, maleamide, fumaramide, benzamide, propionamide, butyramide, palmitamide, stearamide, oleamide, and erucamide are preferred.

[0040] The amount of the acid amide compound used is not particularly limited as long as it is an amount that is effective against compound (2) and compound (3) and suppresses the growth reaction. From the viewpoint of productivity, the amount is preferably in the range of 0.0001 to 10% by mass, more preferably 0.001 to 5% by mass, and even more preferably 0.01 to 1% by mass, relative to compound (2).

[0041] The platinum catalyst used in the present invention can be appropriately selected from known platinum (Pt) and complex compounds having platinum as the central metal. Specific examples include alcohol solutions of chloroplatinic acid, such as a solution of chloroplatinic acid (IV) acid in 2-ethylhexanol; a toluene or xylene solution of a platinum-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex; dichlorobisacetonitrile platinum, dichlorobisbenzonitrile platinum; and dichlorocyclooctadiene platinum. It is also possible to use a catalyst in which platinum black or the like is supported on a carrier such as alumina, silica, or carbon. In particular, from the viewpoint of high reactivity, an alcohol solution of chloroplatinic acid such as a 2-ethylhexanol solution of chloroplatinic (IV) acid, and a toluene or xylene solution of a platinum-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex are preferred.

[0042] The amount of the platinum catalyst used is not particularly limited as long as it is an amount that exerts a catalytic effect in the hydrosilylation reaction. From the viewpoints of reactivity and productivity, the amount of platinum metal used is preferably in the range of 0.0000001 to 1 mol, more preferably 0.000001 to 0.1 mol, and even more preferably 0.00001 to 0.01 mol, per 1 mol of compound (2).

[0043] The reaction temperature in the hydrosilylation reaction is not particularly limited, but from the viewpoints of reactivity and productivity, it is preferably in the range of 50 to 200°C, more preferably 50 to 150°C, and even more preferably 50 to 100°C. The reaction time is not particularly limited, but is preferably in the range of 1 to 30 hours, more preferably 1 to 20 hours, and even more preferably 1 to 10 hours.

[0044] The hydrosilylation reaction proceeds without a solvent, but a solvent can also be used. Examples of the solvent include hydrocarbon solvents such as pentane, hexane, cyclohexane, heptane, isooctane, benzene, toluene, and xylene; ether solvents such as diethyl ether, tetrahydrofuran, and dioxane; ester solvents such as ethyl acetate and butyl acetate; aprotic polar solvents such as acetonitrile and N,N-dimethylformamide; and chlorinated hydrocarbon solvents such as dichloromethane and chloroform. These solvents may be used alone or in combination of two or more.

[0045] In the production method of the present invention, a polymerization inhibitor can be used in addition to the acid amide compound. When an acid amide compound and a polymerization inhibitor are used in combination, the effect of the acid amide compound suppressing the growth reaction of the raw material (meth)acrylate compound and the effect of the polymerization inhibitor suppressing the growth reaction of the raw material (meth)acrylate compound and the product, an organosilicon compound having a (meth)acryloyloxy group, have a mutual effect, and therefore the effect can be enhanced compared to when each is used alone.

[0046] The polymerization inhibitor used in the present invention includes a phenol-based polymerization inhibitor and a hindered phenol-based polymerization inhibitor.

[0047] Examples of phenol-based polymerization inhibitors include methoxyphenol compounds such as 4-methoxyphenol, 2-methyl-4-methoxyphenol, 3-methyl-4-methoxyphenol, 2,3-dimethyl-4-methoxyphenol, 2,5-dimethyl-4-methoxyphenol, 2,6-dimethyl-4-methoxyphenol, 3,5-dimethyl-4-methoxyphenol, 2-tert-butyl-4-methoxyphenol, 3-tert-butyl-4-methoxyphenol, 2-methyl-3-tert-butyl-4-methoxyphenol, 3-tert-butyl-5-methyl-4-methoxyphenol, 2,3-di-tert-butyl-4-methoxyphenol, and 2,5-di-tert-butyl-4-methoxyphenol; Examples of hydroxyphenol compounds include hydroxyphenol, 2-methyl-4-hydroxyphenol, 3-methyl-4-hydroxyphenol, 2,3-dimethyl-4-hydroxyphenol, 2,5-dimethyl-4-hydroxyphenol, 2,6-dimethyl-4-hydroxyphenol, 3,5-dimethyl-4-hydroxyphenol, 2-tert-butyl-4-hydroxyphenol, 3-tert-butyl-4-hydroxyphenol, 2-methyl-3-tert-butyl-4-hydroxyphenol, 3-tert-butyl-5-methyl-4-hydroxyphenol, and 3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-2H-1-benzopyran-6-ol. Among these, 4-methoxyphenol, 2-methyl-4-methoxyphenol, 2-tert-butyl-4-methoxyphenol, and 4-hydroxyphenol are preferred from the viewpoint of availability.

[0048] The amount of the phenol-based polymerization inhibitor used is not particularly limited as long as it is an amount that is effective against compound (2) and compound (3) and suppresses the initiation reaction and the propagation reaction. From the viewpoint of productivity, the amount is preferably in the range of 0.0001 to 10% by mass, more preferably 0.001 to 5% by mass, and even more preferably 0.01 to 1% by mass, relative to compound (2).

[0049] Examples of the hindered phenol polymerization inhibitor include 2,6-di-tert-butyl-4-methylphenol, 2,6-di-tert-butyl-4-ethylphenol, 4,4-methylenebis(2,6-di-tert-butylphenol), 2,2-methylenebis(6-tert-butyl-4-methylphenol), 2,2-methylenebis(6-tert-butyl-4-ethylphenol), 2,6-di-tert-butyl-4-dimethylaminomethylphenol, 2,6-di-tert-butyl-4-methoxyphenol, 2,6-di-tert-butyl-4-hydroxyphenol, pentaerythritol tetrakis[3-(3,5-di-tert-butyl di-tert-butylphenol compounds such as N,N-hexamethylenebis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], 2,2-thiodiethylenebis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, N,N-hexamethylenebis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionamide, 2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)mesitylene, and hexamethylenebis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate]. Among these, di-tert-butylphenol compounds such as 2,6-di-tert-butyl-4-methylphenol, 4,4-methylenebis(2,6-di-tert-butylphenol), 2,2-methylenebis(6-tert-butyl-4-methylphenol), 2,6-di-tert-butyl-4-dimethylaminomethylphenol, 2,6-di-tert-butyl-4-methoxyphenol, and 2,6-di-tert-butyl-4-hydroxyphenol are preferred, particularly from the viewpoint of availability.

[0050] The amount of the hindered phenol-based polymerization inhibitor used is not particularly limited as long as it is an amount that, in combination with the phenol-based polymerization inhibitor, is effective against compound (2) and compound (3) and suppresses the initiation reaction and the propagation reaction. From the viewpoint of productivity, the amount is preferably in the range of 0.0001 to 10% by mass, more preferably 0.001 to 5% by mass, and even more preferably 0.01 to 1% by mass, relative to compound (2).

[0051] In the production method of the present invention, the acid amide compound, the phenol-based polymerization inhibitor, and the hindered phenol-based polymerization inhibitor may be used either alone or as a mixture of two or more kinds from each compound group.

[0052] In the production method of the present invention, in addition to the acid amide compound, the phenol-based polymerization inhibitor, and the hindered phenol-based polymerization inhibitor, a polymerization inhibitor appropriately selected from known polymerization inhibitors effective in radical polymerization can be used, provided that the reactivity of the hydrosilylation reaction is not reduced and no quality problems are caused in the final product, Compound (3). Specific examples thereof include quinone compounds such as p-benzoquinone, methyl-p-benzoquinone, tert-butyl-p-benzoquinone, and 2,5-diphenyl-p-benzoquinone; copper compounds such as cuprous chloride, cupric chloride, cuprous oxide, cupric oxide, copper sulfate, and copper dimethyldithiocarbamate; phenothiazine, diphenylamine, alkylated diphenylamine, phenylenediamine, N,N-diphenyl-p-phenylenediamine, N,N-dinaphthyl-p-phenylenediamine, 4-hydroxy-2,2,6,6-tetramethylpiperidine, 4-benzoyloxy-2,2,6,6-tetramethylpiperidine, 1,4-dihydroxy-2,2,6,6-tetramethylpiperidine, 1-hydroxy-4-benzoyloxy ... Examples of the polymerization inhibitor include nitrogen-containing compounds such as 2,2,6,6-tetramethylpiperidine, tri-n-hexylphosphine, tri-n-octylphosphine, triphenylphosphine, tris(2-methylphenyl)phosphine, tris(4-methylphenyl)phosphine, tris(6-methylphenyl)phosphine, tris(2,4-di-tert-butylphenyl)phosphine, triphenyl phosphine, dialkyldithiophosphate zinc, and diallyldithiophosphate zinc. Examples of the polymerization inhibitor include sulfur-containing compounds such as butyl sulfide, didodecyl 3,3'-thiodipropionate, and tetramethylthiuram disulfide. Examples of the polymerization inhibitor include aliphatic conjugated unsaturated bond-containing compounds such as tung oil, dehydrated castor oil, and conjugated linoleic oil. These polymerization inhibitors can be used alone or in combination of two or more.

[0053] In the production method of the present invention, in addition to the above-mentioned polymerization inhibitor, additives such as antioxidants, vulcanization accelerators, metal deactivators, ultraviolet absorbers, and light stabilizers can be used in combination, provided that they do not decrease the reactivity of the hydrosilylation reaction and do not cause any quality problems in the final product, compound (3). EXAMPLES

[0054] The present invention will be described in more detail below with reference to examples and comparative examples, but the present invention is not limited to the following examples. The ratios of the reaction mixtures shown below were determined by gas chromatography under the following conditions. [Gas chromatography measurement conditions] Gas chromatograph: GC-2014 (Shimadzu Corporation) Packed column: Silicone SE-30 (GL Sciences, Inc.) Detector:TCD Detector temperature: 300℃ Inlet temperature: 300℃ Heating program: 70℃ (0 min) → 10℃ / min → 300℃ (10 min) Carrier gas: Helium (50ml / min) Injection volume: 1μl

[0055] [Example 1] Synthesis of 3-acryloxypropyltrichlorosilane In a flask equipped with a stirrer, reflux condenser, dropping funnel and thermometer, 112.1g (1.000 mol) of allyl acrylate, 0.1g of acetamide (equivalent to 0.1% by mass relative to allyl acrylate), and a 2-ethylhexanol solution of chloroplatinic (IV) acid (0.00001 mol as platinum atoms) were charged at room temperature and heated for 2 hours until the temperature reached 80°C. After the internal temperature stabilized, 135.5g (1.000 mol) of trichlorosilane was added dropwise at 80-100°C over 10 hours, and the mixture was stirred at that temperature for 10 hours. The resulting reaction mixture was analyzed by gas chromatography, and it was confirmed that the area percentage ratio of the raw materials allyl acrylate and trichlorosilane to the product 3-acryloxypropyltrichlorosilane was 6:0:94. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube, which had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 5 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0056] [Example 2] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 1, except that 67.8 g (0.500 mol) of trichlorosilane was added dropwise at 80 to 100° C. over a period of 5 hours. The resulting reaction mixture was analyzed by gas chromatography, and it was confirmed that the area percentage ratio of the raw materials allyl acrylate and trichlorosilane to the product 3-acryloxypropyltrichlorosilane was 46:0:54. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube, which had been thoroughly purged with nitrogen, sealed, and heated to 135° C. to confirm its thermal stability. After 5 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0057] [Example 3] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 1, except that 33.9 g (0.250 mol) of trichlorosilane was added dropwise at 80 to 100° C. over a period of 2.5 hours. The reaction mixture was analyzed by gas chromatography, and it was confirmed that the area percentage ratio of the raw materials allyl acrylate and trichlorosilane to the product 3-acryloxypropyltrichlorosilane was 72:0:28. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube, which had been thoroughly purged with nitrogen, sealed, and heated to 125° C. to confirm its thermal stability. After 5 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0058] [Example 4] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 1, except that 4.1 g (0.030 mol) of trichlorosilane was added dropwise at 80 to 100° C. over 0.3 hours. The reaction mixture was analyzed by gas chromatography, and it was confirmed that the area percentage ratio of the raw materials allyl acrylate and trichlorosilane to the product 3-acryloxypropyltrichlorosilane was 98:0:2. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube, which had been thoroughly purged with nitrogen, sealed, and heated to 115° C. to confirm its thermal stability. After 5 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0059] [Example 5] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 1, except that 0.1 g (corresponding to 0.1% by mass based on allyl acrylate) of benzamide was used instead of acetamide. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube, which had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 5 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0060] [Example 6] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 2, except that 0.1 g (corresponding to 0.1% by mass based on allyl acrylate) of benzamide was used instead of acetamide. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube, which had been thoroughly purged with nitrogen, sealed, and heated to 135° C. to confirm its thermal stability. After 5 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0061] [Example 7] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 3, except that 0.1 g (corresponding to 0.1% by mass based on allyl acrylate) of benzamide was used instead of acetamide. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube, which had been thoroughly purged with nitrogen, sealed, and heated to 125° C. to confirm its thermal stability. After 5 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0062] [Example 8] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 4, except that 0.1 g (corresponding to 0.1% by mass based on allyl acrylate) of benzamide was used instead of acetamide. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube, which had been thoroughly purged with nitrogen, sealed, and heated to 115° C. to confirm its thermal stability. After 5 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0063] [Example 9] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 1, except that 0.1 g of oleamide (corresponding to 0.1% by mass based on allyl acrylate) was used instead of acetamide. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube, which had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 5 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0064] [Example 10] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 2, except that 0.1 g of oleamide (corresponding to 0.1% by mass based on allyl acrylate) was used instead of acetamide. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube, which had been thoroughly purged with nitrogen, sealed, and heated to 135° C. to confirm its thermal stability. After 5 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0065] [Example 11] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 3, except that 0.1 g of oleamide (corresponding to 0.1% by mass based on allyl acrylate) was used instead of acetamide. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube, which had been thoroughly purged with nitrogen, sealed, and heated to 125° C. to confirm its thermal stability. After 5 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0066] [Example 12] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 4, except that 0.1 g of oleamide (corresponding to 0.1% by mass based on allyl acrylate) was used instead of acetamide. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube, which had been thoroughly purged with nitrogen, sealed, and heated to 115° C. to confirm its thermal stability. After 5 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0067] [Example 13] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 1, except that 0.1 g (corresponding to 0.1% by mass based on allyl acrylate) of N-methylacetamide was used instead of acetamide. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube, which had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 5 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0068] [Example 14] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 1, except that 0.1 g (corresponding to 0.1% by mass based on allyl acrylate) of N,N-dimethylacetamide was used instead of acetamide. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube, which had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 5 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0069] [Example 15] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 1, except that 0.1 g (corresponding to 0.1% by mass based on allyl acrylate) of malonamide was used instead of acetamide. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube, which had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 5 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0070] [Example 16] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 1, except that 0.1 g of succinamide (corresponding to 0.1% by mass based on allyl acrylate) was used instead of acetamide. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube, which had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 5 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0071] [Example 17] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 1, except that 0.1 g (corresponding to 0.1% by mass based on allyl acrylate) of maleamide was used instead of acetamide. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube, which had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 5 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0072] [Example 18] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 1, except that 0.1 g of fumaramide (corresponding to 0.1% by mass based on allyl acrylate) was used instead of acetamide. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube, which had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 5 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0073] [Example 19] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 1, except that 0.1 g of propionamide (corresponding to 0.1% by mass based on allyl acrylate) was used instead of acetamide. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube, which had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 5 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0074] [Example 20] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 1, except that 0.1 g (corresponding to 0.1% by mass based on allyl acrylate) of butyramide was used instead of acetamide. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube, which had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 5 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0075] [Example 21] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 1, except that 0.1 g of palmitamide (corresponding to 0.1% by mass based on allyl acrylate) was used instead of acetamide. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube, which had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 5 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0076] [Example 22] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 1, except that 0.1 g of stearamide (corresponding to 0.1% by mass based on allyl acrylate) was used instead of acetamide. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube, which had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 5 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0077] [Example 23] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 1, except that 0.1 g of erucamide (corresponding to 0.1% by mass based on allyl acrylate) was used instead of acetamide. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube, which had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 5 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0078] [Example 24] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 1, except that 0.1 g of 4-methoxyphenol (corresponding to 0.1% by mass based on allyl acrylate) was added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube, which had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 6 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0079] [Example 25] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 1, except that 0.1 g of 2-methyl-4-methoxyphenol (corresponding to 0.1% by mass based on allyl acrylate) was added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube, which had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 6 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0080] [Example 26] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 1, except that 0.1 g of 2-tert-butyl-4-methoxyphenol (corresponding to 0.1% by mass based on allyl acrylate) was added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube, which had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 6 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0081] [Example 27] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 1, except that 0.1 g of 4-hydroxyphenol (corresponding to 0.1% by mass based on allyl acrylate) was added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube, which had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 6 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0082] [Example 28] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 5, except that 0.1 g of 4-methoxyphenol (corresponding to 0.1% by mass based on allyl acrylate) was added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube, which had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 6 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0083] [Example 29] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 5, except that 0.1 g of 2-methyl-4-methoxyphenol (corresponding to 0.1% by mass based on allyl acrylate) was added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube, which had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 6 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0084] [Example 30] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 5, except that 0.1 g (corresponding to 0.1% by mass based on allyl acrylate) of 2-tert-butyl-4-methoxyphenol was added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube, which had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 6 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0085] [Example 31] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 5, except that 0.1 g of 4-hydroxyphenol (corresponding to 0.1% by mass based on allyl acrylate) was added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube, which had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 6 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0086] [Example 32] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 9, except that 0.1 g of 4-methoxyphenol (corresponding to 0.1% by mass based on allyl acrylate) was added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube, which had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 6 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0087] [Example 33] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 9, except that 0.1 g (corresponding to 0.1% by mass based on allyl acrylate) of 2-methyl-4-methoxyphenol was added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube, which had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 6 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0088] [Example 34] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 9, except that 0.1 g (corresponding to 0.1% by mass based on allyl acrylate) of 2-tert-butyl-4-methoxyphenol was added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube, which had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 6 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0089] [Example 35] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 9, except that 0.1 g of 4-hydroxyphenol (corresponding to 0.1% by mass based on allyl acrylate) was added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube, which had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 6 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0090] [Example 36] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 1, except that 0.1 g of 2,6-di-tert-butyl-4-methylphenol (corresponding to 0.1% by mass based on allyl acrylate) was added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube that had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 20 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0091] [Example 37] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 1, except that 0.1 g (corresponding to 0.1% by mass based on allyl acrylate) of 4,4-methylenebis(2,6-di-tert-butylphenol) was added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube that had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 20 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0092] [Example 38] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 1, except that 0.1 g (corresponding to 0.1% by mass based on allyl acrylate) of 2,2-methylenebis(6-tert-butyl-4-methylphenol) was added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube that had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 20 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0093] [Example 39] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 1, except that 0.1 g (corresponding to 0.1% by mass based on allyl acrylate) of 2,6-di-tert-butyl-4-dimethylaminomethylphenol was added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube that had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 20 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0094] [Example 40] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 1, except that 0.1 g (corresponding to 0.1% by mass based on allyl acrylate) of 2,6-di-tert-butyl-4-methoxyphenol was added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube that had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 20 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0095] [Example 41] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 1, except that 0.1 g (corresponding to 0.1% by mass based on allyl acrylate) of 2,6-di-tert-butyl-4-hydroxyphenol was added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube that had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 20 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0096] [Example 42] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 1, except that 0.1 g (corresponding to 0.1% by mass based on allyl acrylate) of 3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-2H-1-benzopyran-6-ol was added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube that had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 20 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0097] [Example 43] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 5, except that 0.1 g (corresponding to 0.1% by mass based on allyl acrylate) of 2,6-di-tert-butyl-4-methylphenol was added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube that had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 20 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0098] [Example 44] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 5, except that 0.1 g (corresponding to 0.1% by mass based on allyl acrylate) of 4,4-methylenebis(2,6-di-tert-butylphenol) was added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube that had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 20 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0099] [Example 45] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 5, except that 0.1 g (corresponding to 0.1% by mass based on allyl acrylate) of 2,2-methylenebis(6-tert-butyl-4-methylphenol) was added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube that had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 20 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0100] [Example 46] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 5, except that 0.1 g (corresponding to 0.1% by mass based on allyl acrylate) of 2,6-di-tert-butyl-4-dimethylaminomethylphenol was added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube that had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 20 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0101] [Example 47] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 5, except that 0.1 g (corresponding to 0.1% by mass based on allyl acrylate) of 2,6-di-tert-butyl-4-methoxyphenol was added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube that had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 20 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0102] [Example 48] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 5, except that 0.1 g (corresponding to 0.1% by mass based on allyl acrylate) of 2,6-di-tert-butyl-4-hydroxyphenol was added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube that had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 20 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0103] [Example 49] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 5, except that 0.1 g (corresponding to 0.1% by mass based on allyl acrylate) of 3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-2H-1-benzopyran-6-ol was added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube that had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 20 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0104] [Example 50] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 9, except that 0.1 g (corresponding to 0.1% by mass based on allyl acrylate) of 2,6-di-tert-butyl-4-methylphenol was added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube that had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 20 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0105] [Example 51] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 9, except that 0.1 g (corresponding to 0.1% by mass based on allyl acrylate) of 4,4-methylenebis(2,6-di-tert-butylphenol) was added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube that had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 20 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0106] [Example 52] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 9, except that 0.1 g (corresponding to 0.1% by mass based on allyl acrylate) of 2,2-methylenebis(6-tert-butyl-4-methylphenol) was added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube that had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 20 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0107] [Example 53] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 9, except that 0.1 g (corresponding to 0.1% by mass based on allyl acrylate) of 2,6-di-tert-butyl-4-dimethylaminomethylphenol was added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube that had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 20 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0108] [Example 54] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 9, except that 0.1 g (corresponding to 0.1% by mass based on allyl acrylate) of 2,6-di-tert-butyl-4-methoxyphenol was added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube that had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 20 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0109] [Example 55] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 9, except that 0.1 g (corresponding to 0.1% by mass based on allyl acrylate) of 2,6-di-tert-butyl-4-hydroxyphenol was added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube that had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 20 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0110] [Example 56] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 9, except that 0.1 g (corresponding to 0.1% by mass based on allyl acrylate) of 3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-2H-1-benzopyran-6-ol was added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube that had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 20 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0111] [Example 57] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 1, except that 0.1 g of 4-methoxyphenol (corresponding to 0.1% by mass relative to allyl acrylate) and 0.1 g of 2,6-di-tert-butyl-4-methylphenol (corresponding to 0.1% by mass relative to allyl acrylate) were added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube that had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 50 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0112] [Example 58] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 1, except that 0.1 g of 4-methoxyphenol (corresponding to 0.1% by mass relative to allyl acrylate) and 0.1 g of 2,2-methylenebis(6-tert-butyl-4-methylphenol) (corresponding to 0.1% by mass relative to allyl acrylate) were added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube that had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 50 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0113] [Example 59] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 1, except that 0.1 g of 4-methoxyphenol (corresponding to 0.1% by mass relative to allyl acrylate) and 0.1 g of 2,6-di-tert-butyl-4-dimethylaminomethylphenol (corresponding to 0.1% by mass relative to allyl acrylate) were added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube that had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 50 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0114] [Example 60] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 1, except that 0.1 g of 4-hydroxyphenol (corresponding to 0.1% by mass relative to allyl acrylate) and 0.1 g of 2,6-di-tert-butyl-4-methylphenol (corresponding to 0.1% by mass relative to allyl acrylate) were added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube that had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 50 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0115] [Example 61] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 1, except that 0.1 g of 4-hydroxyphenol (corresponding to 0.1% by mass relative to allyl acrylate) and 0.1 g of 2,2-methylenebis(6-tert-butyl-4-methylphenol) (corresponding to 0.1% by mass relative to allyl acrylate) were added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube that had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 50 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0116] [Example 62] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 1, except that 0.1 g of 4-hydroxyphenol (corresponding to 0.1% by mass relative to allyl acrylate) and 0.1 g of 2,6-di-tert-butyl-4-dimethylaminomethylphenol (corresponding to 0.1% by mass relative to allyl acrylate) were added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube that had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 50 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0117] [Example 63] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 5, except that 0.1 g of 4-methoxyphenol (corresponding to 0.1% by mass relative to allyl acrylate) and 0.1 g of 2,6-di-tert-butyl-4-methylphenol (corresponding to 0.1% by mass relative to allyl acrylate) were added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube that had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 50 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0118] [Example 64] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 5, except that 0.1 g of 4-methoxyphenol (corresponding to 0.1% by mass relative to allyl acrylate) and 0.1 g of 2,2-methylenebis(6-tert-butyl-4-methylphenol) (corresponding to 0.1% by mass relative to allyl acrylate) were added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube that had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 50 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0119] [Example 65] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 5, except that 0.1 g of 4-methoxyphenol (corresponding to 0.1% by mass relative to allyl acrylate) and 0.1 g of 2,6-di-tert-butyl-4-dimethylaminomethylphenol (corresponding to 0.1% by mass relative to allyl acrylate) were added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube that had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 50 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0120] [Example 66] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 5, except that 0.1 g of 4-hydroxyphenol (corresponding to 0.1% by mass relative to allyl acrylate) and 0.1 g of 2,6-di-tert-butyl-4-methylphenol (corresponding to 0.1% by mass relative to allyl acrylate) were added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube that had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 50 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0121] [Example 67] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 5, except that 0.1 g of 4-hydroxyphenol (corresponding to 0.1% by mass relative to allyl acrylate) and 0.1 g of 2,2-methylenebis(6-tert-butyl-4-methylphenol) (corresponding to 0.1% by mass relative to allyl acrylate) were added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube that had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 50 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0122] [Example 68] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 5, except that 0.1 g of 4-hydroxyphenol (corresponding to 0.1% by mass relative to allyl acrylate) and 0.1 g of 2,6-di-tert-butyl-4-dimethylaminomethylphenol (corresponding to 0.1% by mass relative to allyl acrylate) were added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube that had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 50 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0123] [Example 69] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 9, except that 0.1 g of 4-methoxyphenol (corresponding to 0.1% by mass relative to allyl acrylate) and 0.1 g of 2,6-di-tert-butyl-4-methylphenol (corresponding to 0.1% by mass relative to allyl acrylate) were added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube that had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 50 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0124] [Example 70] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 9, except that 0.1 g of 4-methoxyphenol (corresponding to 0.1% by mass relative to allyl acrylate) and 0.1 g of 2,2-methylenebis(6-tert-butyl-4-methylphenol) (corresponding to 0.1% by mass relative to allyl acrylate) were added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube that had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 50 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0125] [Example 71] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 9, except that 0.1 g of 4-methoxyphenol (corresponding to 0.1% by mass relative to allyl acrylate) and 0.1 g of 2,6-di-tert-butyl-4-dimethylaminomethylphenol (corresponding to 0.1% by mass relative to allyl acrylate) were added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube that had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 50 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0126] [Example 72] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 9, except that 0.1 g of 4-hydroxyphenol (corresponding to 0.1% by mass relative to allyl acrylate) and 0.1 g of 2,6-di-tert-butyl-4-methylphenol (corresponding to 0.1% by mass relative to allyl acrylate) were added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube that had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 50 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0127] [Example 73] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 9, except that 0.1 g of 4-hydroxyphenol (corresponding to 0.1% by mass relative to allyl acrylate) and 0.1 g of 2,2-methylenebis(6-tert-butyl-4-methylphenol) (corresponding to 0.1% by mass relative to allyl acrylate) were added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube that had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 50 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0128] [Example 74] Synthesis of 3-acryloxypropyltrichlorosilane The reaction was carried out in the same manner as in Example 9, except that 0.1 g of 4-hydroxyphenol (corresponding to 0.1% by mass relative to allyl acrylate) and 0.1 g of 2,6-di-tert-butyl-4-dimethylaminomethylphenol (corresponding to 0.1% by mass relative to allyl acrylate) were added. The reaction mixture (10 g) was placed in a 20 ml screw-top test tube that had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 50 hours, the reaction mixture remained fluid and showed no tendency to self-polymerize.

[0129] [Comparative Example 1] Stability test of allyl acrylate 10 g of allyl acrylate was placed in a 20 ml screw-top test tube that had been thoroughly purged with nitrogen, sealed, and heated to 115° C. to confirm its thermal stability. After 0.1 hours, the allyl acrylate lost its fluidity and self-polymerized to solidify.

[0130] [Comparative Example 2] Stability test of allyl acrylate 10 g of allyl acrylate and 0.0025 g of 4-methoxyphenol (corresponding to 0.025% by mass of allyl acrylate) were placed in a 20 ml screw-top test tube that had been thoroughly substituted with nitrogen, sealed, and heated to 115° C. to confirm thermal stability. After 7 hours, the allyl acrylate lost its fluidity and self-polymerized to solidify.

[0131] [Comparative Example 3] Stability test of allyl acrylate 10 g of allyl acrylate and 0.0025 g of 2,6-di-tert-butyl-4-methylphenol (corresponding to 0.025% by mass of allyl acrylate) were placed in a 20 ml screw-top test tube that had been thoroughly substituted with nitrogen, sealed, and heated to 115° C. to confirm thermal stability. After 0.1 hours, the allyl acrylate lost its fluidity and self-polymerized to solidify.

[0132] [Reference Example 1] Stability test of allyl acrylate 10 g of allyl acrylate and 0.0025 g of acetamide (corresponding to 0.025% by mass of allyl acrylate) were placed in a 20 ml screw-top test tube that had been thoroughly substituted with nitrogen, sealed, and heated to 115° C. to confirm thermal stability. After 30 hours, the allyl acrylate maintained its fluidity and showed no tendency to self-polymerize.

[0133] [Reference Example 2] Stability test of allyl acrylate 10 g of allyl acrylate and 0.0025 g of benzamide (corresponding to 0.025% by mass of allyl acrylate) were placed in a 20 ml screw-top test tube that had been thoroughly substituted with nitrogen, sealed, and heated to 115° C. to confirm thermal stability. After 30 hours, the allyl acrylate maintained its fluidity and showed no tendency to self-polymerize.

[0134] [Reference Example 3] Stability test of allyl acrylate 10 g of allyl acrylate and 0.0025 g of oleamide (corresponding to 0.025% by mass of allyl acrylate) were placed in a 20 ml screw-top test tube that had been thoroughly purged with nitrogen, sealed, and heated to 115° C. to confirm thermal stability. After 30 hours, the allyl acrylate maintained its fluidity and showed no tendency to self-polymerize.

[0135] [Comparative Example 4] Synthesis of 3-acryloxypropyltrichlorosilane Except for not using acetamide, the reaction was carried out in the same manner as in Example 1. During heating until the temperature reached 80° C., the allyl acrylate lost its fluidity and self-polymerized to solidify before the reaction began.

[0136] [Comparative Example 5] Synthesis of 3-acryloxypropyltrichlorosilane Except for not using acetamide, the reaction was carried out in the same manner as in Example 24. After the start of the dropwise addition of trichlorosilane, the reaction mixture lost its fluidity and self-polymerized during the reaction, solidifying.

[0137] [Comparative Example 6] Synthesis of 3-acryloxypropyltrichlorosilane Except for not using acetamide, the reaction was carried out in the same manner as in Example 36. During heating until the temperature reached 80° C., the allyl acrylate lost its fluidity and self-polymerized to solidify before the reaction began.

[0138] [Comparative Example 7] Synthesis of 3-acryloxypropyltrichlorosilane Except for not using acetamide, the reaction was carried out in the same manner as in Example 57. After the dropwise addition of trichlorosilane was completed, the reaction mixture maintained its fluidity and showed no tendency to self-polymerize. 10 g of this reaction mixture was placed in a 20 ml screw-top test tube that had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 3 hours, the reaction mixture lost its fluidity and solidified due to self-polymerization.

[0139] [Comparative Example 8] Synthesis of 3-acryloxypropyltrichlorosilane Except for not using acetamide, the reaction was carried out in the same manner as in Example 58. After the dropwise addition of trichlorosilane was completed, the reaction mixture maintained its fluidity and showed no tendency to self-polymerize. 10 g of this reaction mixture was placed in a 20 ml screw-top test tube that had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 3 hours, the reaction mixture lost its fluidity and solidified due to self-polymerization.

[0140] [Comparative Example 9] Synthesis of 3-acryloxypropyltrichlorosilane Except for not using acetamide, the reaction was carried out in the same manner as in Example 59. After the dropwise addition of trichlorosilane was completed, the reaction mixture maintained its fluidity and showed no tendency to self-polymerize. 10 g of this reaction mixture was placed in a 20 ml screw-top test tube that had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 3 hours, the reaction mixture lost its fluidity and solidified due to self-polymerization.

[0141] [Comparative Example 10] Synthesis of 3-acryloxypropyltrichlorosilane Except for not using acetamide, the reaction was carried out in the same manner as in Example 60. After the dropwise addition of trichlorosilane was completed, the reaction mixture maintained its fluidity and showed no tendency to self-polymerize. 10 g of this reaction mixture was placed in a 20 ml screw-top test tube that had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 3 hours, the reaction mixture lost its fluidity and solidified due to self-polymerization.

[0142] [Comparative Example 11] Synthesis of 3-acryloxypropyltrichlorosilane Except for not using acetamide, the reaction was carried out in the same manner as in Example 6. After the dropwise addition of trichlorosilane was completed, the reaction mixture maintained its fluidity and showed no tendency to self-polymerize. 10 g of this reaction mixture was placed in a 20 ml screw-top test tube that had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 3 hours, the reaction mixture lost its fluidity and solidified due to self-polymerization.

[0143] [Comparative Example 12] Synthesis of 3-acryloxypropyltrichlorosilane Except for not using acetamide, the reaction was carried out in the same manner as in Example 62. After the dropwise addition of trichlorosilane was completed, the reaction mixture maintained its fluidity and showed no tendency to self-polymerize. 10 g of this reaction mixture was placed in a 20 ml screw-top test tube that had been thoroughly purged with nitrogen, sealed, and heated to 150° C. to confirm its thermal stability. After 3 hours, the reaction mixture lost its fluidity and solidified due to self-polymerization.

[0144] [Table 1]

[0145] [Table 2]

[0146] [Table 3]

[0147] [Table 4]

[0148] [Table 5]

[0149] As shown in Tables 1 to 5, in order to stably produce an organosilicon compound having a (meth)acryloyloxy group without self-polymerization, it is important to use an acid amide compound. In Examples 1 to 23, the acid amide compound inhibited the growth reaction of the (meth)acrylate compound, which is the raw material, before and during the reaction, and the organosilicon compound having a (meth)acryloyloxy group, which is the product during and after the reaction. As a result, the organosilicon compound having a (meth)acryloyloxy group could be stably produced without self-polymerization. Since the acid amide compound does not have a structure such as a hydroxyl group that captures radical species, it has not been considered to act as a polymerization inhibitor. However, the acid amide compound has tautomerism, and the acid imide compound, which is the tautomer of the acid amide compound, has a hydroxyl group. Since this acid imide compound has a sterically hindered substituent around the hydroxyl group, it is considered that the hydroxyl group does not react with the halosilane compound. As a result, it is considered that the radical species generated in the presence of the halosilane compound can be quickly captured, and the organosilicon compound having a (meth)acryloyloxy group can be stably produced without self-polymerization. Furthermore, it is clear that the combined use of an acid amide compound and a polymerization inhibitor provides a higher effect than the use of each compound alone. In Examples 24 to 56, the mutual effect of the acid amide compound and the phenol-based heavy industry inhibitor or the hindered phenol-based heavy industry inhibitor made the organosilicon compound having a (meth)acryloyloxy group more stable after the reaction was completed. In Examples 57 to 74, the mutual effect of the acid amide compound, the phenol-based heavy industry inhibitor, and the hindered phenol-based heavy industry inhibitor made the organosilicon compound having a (meth)acryloyloxy group even more stable after the reaction was completed.

[0150] On the other hand, in Comparative Examples 1 to 3, when the acid amide compound was not present, the effect of the phenol-based polymerization inhibitor or the hindered phenol-based polymerization inhibitor was insufficient, and the growth reaction of the raw material (meth)acrylate compound easily proceeded, causing self-polymerization before the start of the reaction. In contrast to the above Comparative Examples 1 to 3, in Reference Examples 1 to 3, the acid amide compound inhibited the growth reaction of the raw material (meth)acrylate compound, causing no self-polymerization. In Comparative Examples 4 to 12, when the acid amide compound was not present, the effects of the phenol-based polymerization inhibitor and the hindered phenol-based polymerization inhibitor, either alone or in combination, were insufficient, and self-polymerization occurred before the start of the reaction and after the end of the reaction.

Claims

1. The following general formula (1) 【Chemistry 1】 (In the formula, R 1 represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, X represents a halogen atom, and n represents an integer of 1 to 3. and a hydrohalosilane compound represented by the following general formula (2): 【Chemistry 2】 (In the formula, R 2 represents a hydrogen atom or a methyl group, R 3 represents an unsubstituted divalent hydrocarbon group having 1 to 18 carbon atoms. and a (meth)acrylate compound having an alkenyl group represented by the following general formula (4): 【Chemistry 3】 (In the formula, R 4 represents a hydrogen atom or a substituted or unsubstituted k-valent hydrocarbon group having 1 to 30 carbon atoms; R 5 each independently represents a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 30 carbon atoms, and k represents an integer of 1 or 2. (However, primary acid amide compounds represented by the following general formula (5) are excluded. ) or the following general formula (5): 【Chemistry 4】 (In the formula, R 6 represents a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 30 carbon atoms. The present invention relates to a method for producing a compound represented by the following general formula (3): 【Chemistry 5】 (In the formula, R 1 , R 2 , R 3 , X and n have the same meanings as above. The present invention relates to a method for producing an organosilicon compound having an acryloxy group or a methacryloxy group, the compound being represented by the formula:

2. 2. The method for producing an organosilicon compound having an acryloxy group or a methacryloxy group according to claim 1, wherein the acid amide compound is one or more selected from the group consisting of acetamide, N-methylacetamide, N,N-dimethylacetamide, malonamide, succinamide, maleamide, fumaramide, benzamide, propionamide, butyramide, palmitamide, stearamide, oleamide, and erucamide.

3. 3. The method for producing an organosilicon compound having an acryloxy group or a methacryloxy group according to claim 1, wherein the hydrosilylation reaction is carried out in the presence of a polymerization inhibitor.

4. 4. The method for producing an organosilicon compound having an acryloxy group or a methacryloxy group according to claim 3, wherein the polymerization inhibitor is a phenol-based polymerization inhibitor or a hindered phenol-based polymerization inhibitor.

5. 5. The method for producing an organosilicon compound having an acryloxy group or a methacryloxy group according to claim 4, wherein the phenol-based polymerization inhibitor is one or more selected from the group consisting of 4-methoxyphenol, 2-methyl-4-methoxyphenol, 2-tert-butyl-4-methoxyphenol, and 4-hydroxyphenol.

6. The method for producing an organosilicon compound having an acryloxy group or methacryloxy group according to claim 4, wherein the hindered phenol-based polymerization inhibitor is one or more selected from 2,6-di-tert-butyl-4-methylphenol, 4,4-methylenebis(2,6-di-tert-butylphenol), 2,2-methylenebis(6-tert-butyl-4-methylphenol), 2,6-di-tert-butyl-4-dimethylaminomethylphenol, 2,6-di-tert-butyl-4-methoxyphenol, 2,6-di-tert-butyl-4-hydroxyphenol, and 3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-2H-1-benzopyran-6-ol.

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