JP2022038140A - Method for producing organosilicon compound - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a method for efficiently producing an organosilicon compound, particularly an organoamid-1-ethyl group- or organoimide-1-ethyl group-containing organosilicon compound.
SOLUTION: An organic silicon compound, particularly an organic silicon compound, in which (a) a predetermined alkenylamide compound or an alkenylimide compound and (b) a predetermined silane compound or a siloxane compound are reacted in the presence of (c) a hydrosilylation reaction catalyst. , A method for producing an organic silicon compound containing an organoamide-1-ethyl group or an organoimide-1-ethyl group.
[Selection diagram] None

Description

The present invention relates to a method for producing an organosilicon compound, and more particularly to a method for producing an organosilicon compound containing an organoamide-1-ethyl group or an organoimide-1-ethyl group.

Silane compounds and siloxane compounds having an amino group utilize the adsorptivity and reactivity of the amino group to modify the surface of fillers, modify resins, modify fiber treatment agents and paint additives, raw materials for cosmetics, etc. It is also used as a synthetic raw material for functional products and is widely used.
However, among the silane compounds and siloxane compounds having a primary amino group, particularly reported examples of the primary aminomethylsilane compound and the siloxane compound in which the carbon chain which is the linking group between the silicon atom and the amino group is 1. And there are few synthetic examples.

For example, Patent Document 1 reports a primary aminomethyl functional polysiloxane and a method for producing the same. Specifically, there is a method for synthesizing a primary aminomethyl-modified polysiloxane at both ends by reacting a polysiloxane having a hydroxyl group at the end of the molecular chain with a monoalkoxysilane having a primary aminomethyl group. It has been reported that the obtained primary aminomethyl-modified polysiloxane at both ends can be used as a raw material for a siloxane-modified polyimide.

Patent Document 2 proposes a siloxane mixture containing a siloxane compound having a primary aminomethyl group and a method for producing the same, but no example of carrying out these is reported, and the production method of Patent Document 2 is used. It is unclear whether it can actually be manufactured.

Patent Document 3 describes a side chain primary aminomethyl-modified polysiloxane in which substituents on the D unit (R ² SiO _2/2 ) and T unit (RSiO _3/2 ), which are structural units of siloxane, are modified. Compounds and branched primary aminomethyl-modified polysiloxane compounds have been reported. Specifically, a dialkoxysilane or trialkoxysilane having a primary aminomethyl group can be used as a raw material, and this can be reacted with a polysiloxane compound having a hydroxyl group at the end of the molecular chain to obtain a target compound. It has been reported that it can be done.

As described in Non-Patent Document 1, the alkoxysilane having a primary aminomethyl group used in Patent Documents 1 to 3 generally contains ammonia in an alkoxysilane having a chloromethyl group at a high temperature and high pressure. It is known to be obtained by reacting below.
However, Non-Patent Document 1 states that a pressure-resistant container must be used when reacting an alkoxysilane having a chloromethyl group with ammonia under high temperature and high pressure, and further, in the alkylation reaction of ammonia. It has been described that not only mono-substituted compounds but also di-substituted compounds are by-produced, and it cannot be said that the reaction method is efficient.

Patent Document 4 reports a method for synthesizing a disiloxane having a primary aminomethyl group. Specifically, disiloxane having a chloromethyl group is reacted with sodium azide to azide, and then hydrogenation is performed for synthesis.
However, it has been difficult to mass-produce azide compounds because of the potential risk of explosion and the like.

Further, Non-Patent Documents 2 and 3 report hydrosilylation reactions of phenyldimethylsilane, enamide and N-vinylurea using rhodium acetate. According to these non-patent documents, it has been reported that a compound in which a silicon atom is added on an adjacent carbon atom of a nitrogen atom of an amide group can be obtained, specifically, 1- (dimethylphenylsilyl) alkylamine. The synthesis method of is reported.
However, dimethylphenylsilane is the only silane compound studied in Non-Patent Documents 2 and 3. Further, Non-Patent Document 2 describes that trichlorosilane and triethoxysilane did not react and the raw materials were recovered. In the method of Non-Patent Document 2, alkoxysilane and low-polarity (poly) siloxane were used. It was unclear if it could be applied to the compound. Furthermore, Non-Patent Document 3 uses hydrazine, which is toxic and explosive, and by the method described in Non-Patent Document 3, an alkoxysilane having a primary aminomethyl group or a low-polarity (poly) siloxane can be used. It was unclear if the compound could be synthesized.

Special Table 2005-517949 Special Table 2007-503455 Gazette U.S. Patent Application Publication No. 2006/0122413 Special Table 2018-528156

Journal of the American Chemical Society, 1955, 77, 3493 Journal of Chemical Society, Chemistry Communications, 1994, 2143 Organometallics, 1998, 17, 926

The present inventor has already used a primary amine to deprotect a silane compound or a siloxane compound having an imide methylene skeleton as a method for producing a silane compound or a siloxane compound having a primary aminomethyl group. It has been found that the desired product can be obtained safely, easily and efficiently by carrying out the reaction (Japanese Patent Application No. 2019-147285).
However, in this method, it is necessary to newly synthesize and use a siloxane compound having a chloromethyl group for producing a compound as a raw material. In addition, a large amount of salt is produced during production. Therefore, it is desired to develop a method for efficiently producing a hydrogen siloxane compound which is widely used.

The present invention has been made in view of such circumstances, and is an organic silicon compound useful as a raw material for a silane compound or a siloxane compound having a primary aminomethyl group, particularly an organoamide-1-ethyl group or an organo. It is an object of the present invention to provide a method for efficiently producing an imide-1-ethyl group-containing organic silicon compound.

As a result of diligent studies to achieve the above object, the present inventor has combined the N-alkenylamide compound or N-alkenylimide compound described later with a hydrosilicon compound or a hydrogensiloxane compound as a hydrosilylation reaction catalyst, particularly. , By carrying out a hydrosilylation reaction using a rhodium-based catalyst, selectively, an organic silicon compound represented by the formula (1), (2) or (3) described later, particularly organoamide-1-ethyl. It has been found that a silane compound or a siloxane compound having a group or an organoimide-1-ethyl group can be obtained, and the present invention has been made.

（式（７）中、Ｒ’は、水素原子、非置換または置換の、炭素数１～２０のアルキル基、炭素数６～２０のアリール基および炭素数７～２０のアラルキル基から選ばれる基であり、式（７）および（８）中、Ｒ”は、それぞれ独立して、水素原子または炭素数１～６の１価炭化水素基であり、式（８）中、Ｘは、非置換または置換の炭素数２～２０の２価炭化水素基である。式（７）および（８）中、ｓは、それぞれ独立して０または１である。）
で表される化合物と、
（ｂ）下記（ｂ－１）または（ｂ－２）
（ｂ－１）下記式（４）で表されるシラン化合物

（式中、Ｒ²は、炭素数１～２０のアルキル基、炭素数６～２０のアリール基および炭素数７～２０のアラルキル基から選ばれる基であり、Ｒ³は、炭素数１～６の１価炭化水素基である。ａは、１～３の整数である。）
（ｂ－２）下記式（５）または（６）で表されるシロキサン化合物

（式（５）および（６）中、Ｒ⁵は、それぞれ独立して、水素原子、Ｒ²および－ＯＲ³基（Ｒ²およびＲ³は前記と同じである。）から選ばれる基であるが、式（５）および（６）のそれぞれにおいて、Ｒ⁵のうち１個以上が水素原子である。式（５）中、ｍは、０～１，０００の数、ｎは、０～２００の数であり、ｍ＋ｎは、０～１，２００の数であり、ｍ＋ｎで括られた繰り返し単位の配置は、ブロックでもランダムでもよい。式（６）中、ｙは、１～８の正数、ｚは、０～７の数であって、かつｙ＋ｚは、３～８の正数であり、ｙ＋ｚで括られた繰り返し単位の配置は、ブロックでもランダムでもよい。）
で示される１分子中に１個以上のヒドロシリル基を有する有機ケイ素化合物とを
（ｃ）ヒドロシリル化反応触媒の存在下で反応させて、式（７）または（８）と式（４）とに対応して下記式（１）で表される化合物、式（７）または（８）と式（５）とに対応して下記式（２）で表される化合物、式（７）または（８）と式（６）とに対応して下記式（３）で表される化合物

［式（１）および（２）中、Ｒ¹は、下記式（７’）または（８’）

（式中、Ｒ’、Ｒ”、Ｘおよびｓは、前記と同じである。破線は、ケイ素原子との結合手を示す。）
で表される基であり、式（２）および（３）中、Ｒ⁴は、それぞれ独立して、Ｒ¹、Ｒ²および－ＯＲ³基（Ｒ¹～Ｒ³は前記と同じである。以下同じ。）から選ばれる基であり、Ｒ^5’は、それぞれ独立して、水素原子、Ｒ¹、Ｒ²および－ＯＲ³基から選ばれる基であり、式（１）中のＲ²、Ｒ³およびａ、式（２）中のｍおよびｎ、式（３）中のｙおよびｚは前記と同じであるが、式（２）および（３）は、それぞれ１個以上のＲ¹を有する。］
を得る有機ケイ素化合物の製造方法、
２． （ｃ）成分のヒドロシリル化反応触媒が、ロジウム化合物である１記載の有機ケイ素化合物の製造方法、
３． （ｃ）成分のヒドロシリル化反応触媒が、カルボン酸ロジウム、シクロオクタジエンロジウムクロリドダイマーおよびシクロオクタジエンロジウムメトキシドダイマーから選ばれるロジウム化合物である１または２記載の有機ケイ素化合物の製造方法、
４． さらに、１～３のいずれかに記載の方法によって製造された式（１）、（２）または（３）で表される有機ケイ素化合物を用いて重合反応する工程を含む１～３のいずれかに記載の有機ケイ素化合物の製造方法、
５． 前記重合反応において、重合触媒を添加する４記載の有機ケイ素化合物の製造方法
を提供する。 That is, the present invention
1. 1. (A) The following formula (7) or (8)

(In formula (7), R'is a hydrogen atom, an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms and an aralkyl group having 7 to 20 carbon atoms. In the formulas (7) and (8), R "is independently a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms, and in the formula (8), X is unsubstituted. Alternatively, it is a divalent hydrocarbon group having 2 to 20 carbon atoms. In the formulas (7) and (8), s is 0 or 1 independently.)
And the compound represented by
(B) The following (b-1) or (b-2)
(B-1) Silane compound represented by the following formula (4)

(In the formula, R ² is a group selected from an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms and an aralkyl group having 7 to 20 carbon atoms, and R ³ is a group having 1 to 6 carbon atoms. It is a monovalent hydrocarbon group of. A is an integer of 1 to 3.)
(B-2) A siloxane compound represented by the following formula (5) or (6)

(In formulas (5) and (6), R ⁵ is a group independently selected from a hydrogen atom, R ² and −OR ³ groups (R ² and R ³ are the same as described above). However, in each of the formulas (5) and (6), one or more of R ⁵ is a hydrogen atom. In the formula (5), m is a number of 0 to 1,000 and n is 0 to 200. M + n is a number from 0 to 1,200, and the arrangement of repeating units enclosed by m + n may be block or random. In equation (6), y is a positive number from 1 to 8. , Z is a number from 0 to 7, and y + z is a positive number from 3 to 8, and the arrangement of the repeating units enclosed by y + z may be block or random.)
An organosilicon compound having one or more hydrosilyl groups in one molecule represented by (c) is reacted in the presence of (c) a hydrosilylation reaction catalyst to form the formula (7) or (8) and the formula (4). Correspondingly, the compound represented by the following formula (1), the compound represented by the following formula (2) corresponding to the formula (7) or (8) and the formula (5), the formula (7) or (8). ) And the compound represented by the following formula (3) corresponding to the formula (6).

[In the equations (1) and (2), R ¹ is the following equation (7') or (8').

(In the formula, R', R ", X and s are the same as described above. The broken line indicates a bond with a silicon atom.)
In the formulas (2) and (3), R ⁴ is independently represented by R ¹ , R ² and −OR ³ groups (R ¹ to R ³ are the same as described above). The same applies hereinafter.), And R ^5'is a group independently selected from hydrogen atom, R ¹ , R ² and −OR ³ groups, respectively, and R ² in the formula (1), R ³ and a, m and n in formula (2), y and z in formula (3) are the same as above, but formulas (2) and (3) each have one or more R ^1s . Have. ]
How to make organosilicon compounds,
2. 2. (C) The method for producing an organosilicon compound according to 1, wherein the hydrosilylation reaction catalyst of the component is a rhodium compound.
3. 3. (C) The method for producing an organic silicon compound according to 1 or 2, wherein the hydrosilylation reaction catalyst of the component is a rhodium compound selected from rhodium carboxylate, cyclooctadiene rhodium chloride dimer and cyclooctadiene rhodium methoxydo dimer.
4. Further, any one of 1 to 3 including a step of polymerizing using the organosilicon compound represented by the formula (1), (2) or (3) produced by the method according to any one of 1 to 3. The method for producing an organosilicon compound described in 1.
5. The method for producing an organosilicon compound according to 4 in which a polymerization catalyst is added in the polymerization reaction is provided.

According to the production method of the present invention, various raw materials used for producing a silane compound or a siloxane compound having a primary aminomethyl group can be provided. Amino group-containing organic silicon compounds (particularly, silane compounds having a primary aminomethyl group) obtained based on these can be used for surface modification of fillers, resin modification, fiber treatment agents, paint additives, cosmetic raw materials, etc. In addition, it is highly useful because it can be used as a raw material for synthesizing a modified polysiloxane compound having a primary aminomethyl group.
Further, in the silane compound or siloxane compound obtained by the production method of the present invention, the amide group also acts as a hydrophilic group depending on the number of carbon atoms, and particularly when it is bonded to a silicon atom via one carbon atom. It is highly useful because it is considered to be electronically affected by the adjacent silicon atom and can be expected to have properties as a modifier and an additive.

It is a figure which shows the ¹ H-NMR measurement result of the compound obtained in Example 1. FIG. It is a figure which shows the ¹ H-NMR measurement result of the compound obtained in Example 3. FIG. It is a figure which shows the ¹ H-NMR measurement result of the compound obtained in Example 4. It is a figure which shows the ¹ H-NMR measurement result of the other compound obtained in Example 4. It is a figure which shows the ¹ H-NMR measurement result of the compound obtained in Example 5. It is a figure which shows the ¹ H-NMR measurement result of the compound obtained in Application Example 1. FIG.

Hereinafter, the present invention will be described in more detail.
[Manufacturing method of organosilicon compound]
The method for producing an organosilicon compound of the present invention comprises (a) an amide or imide compound containing an alkenyl group, (b) an organosilicon compound having one or more hydrosilyl groups in one molecule, and (c) a hydrosilyl. The reaction is carried out in the presence of a chemical reaction catalyst.

[(A) Alkenyl group-containing amide or imide compound]
The component (a) is an alkenyl group-containing amide compound represented by the following formula (7) or an alkenyl group-containing imide compound represented by the following formula (8), and (b) an organic silicon compound having a hydrosilyl group. (C) The addition reaction in the presence of a hydrosilylation reaction catalyst gives an organic silicon compound represented by the formulas (1), (2) or (3) described later.

In formula (7), R'is a hydrogen atom, an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms and an aralkyl group having 7 to 20 carbon atoms. be.
The alkyl group may be linear, branched or cyclic, preferably having 1 to 10 carbon atoms, more preferably 1 to 8 carbon atoms, and further preferably 1 to 6 carbon atoms. .. Specific examples thereof include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, and the like. Linear or linear such as n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosanyl group. Branched chain alkyl groups; cyclic alkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, norbornyl, adamantyl groups and the like can be mentioned.

The aryl group preferably has 6 to 10 carbon atoms, more preferably 6 to 8 carbon atoms, and specific examples thereof include phenyl, 1-naphthyl, 2-naphthyl, anthryl, phenanthryl, o-biphenylyl, and m-. Examples thereof include biphenylyl, p-biphenylyl group and the like.

The aralkyl group preferably has 7 to 12 carbon atoms, more preferably 7 to 10 carbon atoms, and specific examples thereof include benzyl, phenylethyl, phenylpropyl, naphthylmethyl, naphthylethyl, and naphthylpropyl groups. Be done.

Among these, a hydrogen atom, a linear alkyl group and an aryl group are preferable, an alkyl group having 1 to 3 carbon atoms and a phenyl group are more preferable, and a methyl, ethyl, n-propyl, isopropyl and phenyl groups are more preferable. Therefore, a methyl group and a phenyl group are particularly preferable.
In the alkyl group, aryl group and aralkyl group, a part or all of the hydrogen atom bonded to the carbon atom of these groups may be substituted with a halogen atom such as a fluorine atom or a chlorine atom.

In the formulas (7) and (8), R "is independently a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms. Examples of the monovalent hydrocarbon group include an alkyl group and an aryl. Group etc. can be mentioned.
The alkyl group may be linear, branched or cyclic, and specific examples thereof include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl and n. -Linear or branched alkyl groups such as pentyl and n-hexyl groups; cyclic alkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl groups can be mentioned.
Examples of the aryl group include a phenyl group.
Among these, a hydrogen atom, a methyl group, an ethyl group and a phenyl group are preferable, and a hydrogen atom is more preferable.

In the formula (8), X is an unsubstituted or substituted divalent hydrocarbon group having 2 to 20 carbon atoms, and examples thereof include an alkylene group, an alkenylene group, an arylene group, and an aralkylene group.
The alkylene group may be linear, branched or cyclic, and is preferably an alkylene group having 2 to 14 carbon atoms, more preferably 2 to 10 carbon atoms. Specific examples thereof include ethylene, propylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, heptamethylene, octamethylene, nonamethylene, decamethylene, undecamethylene, dodecamethylene, tridecamethylene, tetradecamethylene, pentadecamethylene, and the like. Linear or branched alkylene groups such as hexadecamethylene, heptadecamethylene, octadecamethylene, nonadecamethylene, eikosadesilene groups; 1,2-cyclohexylene group, 1,4-cyclohexylene group, etc. Cyclic alkylene group and the like can be mentioned.

The alkenylene group may be linear, branched or cyclic, preferably an alkenylene group having 2 to 10 carbon atoms, more preferably an alkenylene group having 2 to 6 carbon atoms, and specific examples thereof include ethenylene and propenylene. , Butenylene, linear or branched chain alkenylene groups such as 1-methyl-1-butenylene groups and the like.

The arylene group is preferably an arylene group having 6 to 12 carbon atoms, more preferably 6 to 10 carbon atoms, and specific examples thereof include o-phenylene, m-phenylene, p-phenylene and 1,2-naphthylene. , 1,8-naphthylene, 2,3-naphthylene, 4,4'-biphenylene group and the like.

The aralkylene group is preferably an aralkylene group having 7 to 16 carbon atoms, more preferably 7 to 12 carbon atoms, and specific examples thereof include-(CH ₂ ) _k -Ar- (Ar has 6 to 6 carbon atoms). It represents 19 arylene groups, and the same examples as above may be mentioned as specific examples thereof. K represents an integer of 1 to 10. The same shall apply hereinafter), -Ar- (CH ₂ ) _k -,-(CH ₂ ). Examples thereof include _j -Ar- (CH ₂ ) _j- (j represents an integer of 1 to 10 independently of each other).

Among these, as the divalent hydrocarbon group having 2 to 20 carbon atoms of X, an alkylene group having 2 to 6 carbon atoms, an alkenylene group having 2 to 5 carbon atoms, and an arylene group having 6 to 8 carbon atoms are preferable. It is preferably an ethylene group, an ethenylene group, or an o-phenylene group.
In the alkylene group, alkenylene group, arylene group and aralkylene group, a part or all of the hydrogen atom bonded to the carbon atom of these groups may be substituted with a halogen atom such as a fluorine atom or a chlorine atom. ..

In formulas (7) and (8), s is independently 0 or 1, preferably 0.

Specific examples of the compound represented by the formula (7) include, but are not limited to, the following. These may be used alone or in combination of two or more.

Specific examples of the compound represented by the formula (8) include, but are not limited to, the following. These may be used alone or in combination of two or more.

[(B) Organosilicon compound having a hydrosilyl group]
The component (b) is an organosilicon compound having one or more hydrosilyl groups in one molecule represented by the following (b-1) or (b-2). The addition reaction with the component (a) gives an organosilicon compound represented by the formula (1), (2) or (3) described later.

(B-1) Silane compound having a hydrosilyl group and a hydrolyzable group The component (b-1) is represented by the following formula (4) and has one hydrosilyl group and one or more hydrolyzable groups in one molecule. It is a silane compound having a sex group.

In formula (4), R ² is a group selected from an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, and an aralkyl group having 7 to 20 carbon atoms.
Specific examples of the alkyl group, aryl group and aralkyl group include groups similar to those exemplified for R'in the formula (7).
R ³ is a monovalent hydrocarbon group having 1 to 6 carbon atoms, and specific examples of the monovalent hydrocarbon group include the same groups as those exemplified for R "in the formulas (7) and (8). be able to.
a is an integer of 1 to 3, preferably 2.

Specific examples of the compound represented by the formula (4) include trimethoxysilane, triethoxysilane, triisopropoxysilane, dimethoxymethylsilane, diethoxymethylsilane, dimethoxyphenylsilane, and diethoxyphenylsilane. Examples thereof include methoxydimethylsilane, ethoxydimethylsilane, diphenylmethoxysilane, and diphenylethoxysilane. These may be used alone or in combination of two or more.

(B-2) Siloxane compound having a hydrosilyl group (b-2) The component (b-2) is a siloxane compound having one or more hydrosilyl groups in one molecule represented by the following formula (5) or (6).

In the formula (5) or (6), R ⁵ is independently a hydrogen atom, R ² and −OR ³ (R ² and R ³ are the same as those described in the formula (4). It is a group selected from.), And is preferably R ² . However, in each of the compounds of the formulas (5) and (6), one or more, particularly two or more, of all R ⁵ are hydrogen atoms.
In the formula (5), m is a number of 0 to 1,000, preferably a number of 0 to 100, and n is a number of 0 to 200, preferably a number of 0 to 50. m + n is a number from 0 to 1,200. Further, the arrangement of repeating units enclosed by m + n may be block or random.
In the formula (6), y is a positive number from 1 to 8, preferably a positive number from 1 to 5, and z is a number from 0 to 7, preferably a number from 0 to 4. , And y + z is a positive number of 3 to 8, preferably a positive number of 3 to 6. Further, the arrangement of the repeating unit enclosed by y + z may be block or random.
In the formulas (5) and (6), the degree of polymerization reflecting the number of repetitions of the siloxane unit can be determined by, for example, ²⁹ Si-NMR analysis.

Specific examples of the compound represented by the formula (5) include pentamethyldisiloxane, tetramethyldisiloxane, hexamethyltrisiloxane, heptamethyltrisiloxane, octamethyltetrasiloxane, and dimethylhydrogensiloxy group-terminated blocking dimethyl. Polysiloxane, dimethylhydrogensiloxy group-terminated blockage, methylhydrogenpolysiloxane, dimethylhydrogensiloxy group-terminated blockade (dimethylsiloxane / methylphenylsiloxane) copolymer, dimethylhydrogensiloxy group-terminated blockade (dimethylsiloxane / methylhydrogensiloxane) ) Copolymer, dimethylhydrogensiloxy group-terminated block (dimethylsiloxane, methylhydrogensiloxane, methylphenylsiloxane) copolymer, trimethylsiloxy group-terminated blocker, methylhydrogenpolysiloxane, trimethylsiloxy group-terminated blocker (dimethylsiloxane, methyl) Hydrosiloxane) copolymer, trimethylsiloxy group-terminated blockade (dimethylsiloxane, methylphenylsiloxane, methylhydrogensiloxane) copolymer, terminal hydroxygroup blockade (dimethylsiloxane, methylhydrogensiloxane) copolymer, one-ended dimethylhydro Examples thereof include dimethylpolysiloxane, which is a genciloxy group-blocking dimethylpolysiloxane. These may be used alone or in combination of two or more.

Specific examples of the compound represented by the formula (6) include trimethylcyclotrisiloxane, tetramethylcyclotrisiloxane, pentamethylcyclotrisiloxane, tetramethyltetrasiloxane, pentamethylcyclotetrasiloxane, and hexamethylcyclotetrasiloxane. , Propyltetramethylcyclotetrasiloxane, dipropyltetramethylcyclotetrasiloxane, pentamethylcyclopentasiloxane, heptamethylcyclopentasiloxane, octamethylcyclopentasiloxane and the like. These may be used alone or in combination of two or more.

The ratio of the component (a) to the component (b) used in the production method of the present invention is not particularly limited, but the molar ratio of the alkenyl group in the component (a) / the hydrosilyl group in the component (b) is , 1/10 to 10/1, more preferably 1/5 to 5/1, and even more preferably 1/3 to 3/1.

[(C) Hydrosilylation reaction catalyst]
The component (c) is a hydrosilylation reaction catalyst. It is used to promote the hydrosilylation reaction between the component (a) and the component (b).
Examples of the hydrosilylation reaction catalyst include platinum-based catalysts such as platinum compounds such as Karstedt's catalyst and Spieer's catalyst; Wilkinson complex, cyclooctadiene rhodium chloride dimer, cyclooctadiene rhodium methoxydo dimer, and rhodium (III) acetylacetate. Compounds such as nat, rhodium acetate (rhodium (II) acetate), rhodium 2-ethylhexanoate (rhodium (II) 2-ethylhexanoate), rhodium octanate (rhodium (II) octanoate) and dimers thereof. Rhodium-based catalysts such as rhodium compounds such as rhodium acid and rhodium chloride; compounds of various metals such as Pd, Ru, Fe, Co and Ni can be mentioned. These may be used alone or in combination of two or more.
Among these, rhodium compounds are preferable in terms of catalytic activity and selectivity, and more preferably rhodium acetate, rhodium 2-ethylhexanoate, rhodium octanate, rhodium carboxylates such as these dimers, cyclooctadiene rhodium chloride dimer, and the like. Cyclooctadiene rhodium methoxyd dimer is more preferred.

The amount of the catalyst is not particularly limited, but from the viewpoint of economy and reactivity, the amount of metal in the catalyst is 0. It is preferably 0.001 to 10 parts by mass, and more preferably 0.0001 to 1 part by mass.

The hydrosilylation reaction can be carried out without a solvent, but an organic solvent may be used as the solvent as long as the reaction is not inhibited. Examples of the organic solvent include aliphatic hydrocarbon compounds such as hexane, heptane and cyclohexane, aromatic hydrocarbon compounds such as toluene and xylene, and ether compounds such as ethylene glycol dimethyl ether, diethylene glycol dimethyl ether and tetrahydrofuran.

When using an organic solvent, it is not preferable to use too much in consideration of catalytic activity and economy. Specifically, 0.1 to 500 parts by mass is preferable with respect to 100 parts by mass of the total solid content containing the components (a) to (c) to be solutes.

Further, in the hydrosilylation reaction, a ligand may be added as long as the reaction is not inhibited. Examples of the ligand include cyclic olefins such as norbornene, norbornadiene and 1,5-cyclooctadiene, phosphine compounds such as triphenylphosphine, and amine compounds such as triethylamine. Since it becomes a catalytic poison of the catalyst, it is preferable to react without adding it.

In the production method of the present invention, the components (a) to (c) and other components used as necessary may be added all at once, or may be added separately in several components. good.
The reaction conditions for the hydrosilylation reaction are not particularly limited, but the reaction temperature is preferably room temperature (20 ± 5 ° C.) to 150 ° C., more preferably 50 to 120 ° C. The reaction time is preferably 0.5 to 48 hours.
After the reaction, the obtained reaction product may be used as it is, or the solvent and volatile components may be distilled off under reduced pressure. Further, the residual catalyst may be adsorbed and purified using activated carbon or the like.

The organosilicon compound obtained by the production method of the present invention is represented by the following formulas (1), (2) or (3).

In formulas (1) and (2), R ¹ is a group represented by the following formula (7') or (8').

（式中、Ｒ’、Ｒ”、Ｘおよびｓは、前記と同じである。破線は、ケイ素原子との結合手を示す。）

(In the formula, R', R ", X and s are the same as described above. The broken line indicates a bond with a silicon atom.)

In formulas (2) and (3), R ⁴ is a group independently selected from R ¹ , R ² and −OR ³ groups (R ¹ to R ³ are the same as described above).
R ^5'is a group independently selected from a hydrogen atom, R ¹ , R ² and -OR ³ groups (R ¹ to R ³ are the same as described above).
Specific examples of the —OR ³ group include methoxy, ethoxy, propoxy group and the like.
The a in the formula (1), m and n in the formula (2), and y and z in the formula (3) are the same as described above. However, each of the organosilicon compounds represented by the formulas (2) and (3) has one or more, particularly two or more R ^1s (groups represented by the formula (7) or (8)) in one molecule. Have.
In the formulas (2) and (3), the degree of polymerization reflecting the number of repetitions of the siloxane unit can be determined by, for example, ²⁹ Si-NMR analysis.
The above-mentioned compound obtained by the production method of the present invention is represented by the corresponding formula (1) from the compound represented by the formula (7) or (8) and the compound represented by the formula (4), respectively. A compound can be obtained, and a compound represented by the corresponding formula (2) can be obtained from the compound represented by the formula (7) or (8) and the compound represented by the formula (5). From the compound represented by (7) or (8) and the compound represented by the formula (6), the corresponding compound represented by the formula (3) can be obtained.

Specific examples of the organosilicon compound represented by the formula (1) include, but are not limited to, the following.

Specific examples of the organosilicon compound represented by the formula (2) include, but are not limited to, the following.

（式中、ｍおよびｎは、前記と同じである。）

(In the formula, m and n are the same as described above.)

Specific examples of the organosilicon compound represented by the formula (3) include, but are not limited to, the following.

In the present invention, further, a part of the organosilicon compound produced by the production method of the present invention, for example, an alkoxysilane compound represented by the formula (1) is used in the presence or absence of a base or an acidic catalyst. By carrying out the polymerization reaction below, the organosilicon compound represented by the formula (2) in the present invention can be produced.
By this polymerization step, the degree of polymerization represented by m and n of the amino group-containing organosilicon compound represented by the formula (2) can be increased. The polymerization reaction can be carried out by a known method.

Further, for example, a base catalyst is used as a catalyst, and the compound of m = 0 and n = 0 in the formula (2) is used as a terminal source, and this is used as a cyclic siloxane (for example, 1,1,3,3,5,5-). By reacting with hexamethylcyclotrisiloxane, 1,1,3,3,5,5,7,7-octamethylcyclotetrasiloxane, etc.), the formula (7') or (8') is applied to one end or both ends. ) Can be obtained as a polydimethylsiloxane compound having a group represented by (2) (when m ≧ 1 and n = 0 in the formula (2)). Further, by adding a terminal source compound such as 1,1,1,3,3,3-hexamethyldisiloxane and reacting with the cyclic siloxane and the compound represented by the formula (3), the formula is added to the side chain. A polysiloxane compound having a group represented by (7') or (8') (in the case of formula (2), where m ≧ 0 and n ≧ 1) can be obtained.

Examples of the base catalyst include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide and silanolate salts of these compounds, quaternary ammonium hydroxides such as hydroxytetramethylammonium, and silanolate salts of these compounds, hydroxy. A quaternary phosphonium hydroxide such as tetrabutylphosphonium and a silanolate salt of these compounds can be used.
As the acid catalyst, hydrochloric acid, sulfuric acid, p-toluenesulfonic acid, acetic acid, trifluoroacetic acid, trifluoromethanesulfonic acid and the like can be used.
When a catalyst is used, the blending amount is 0.001 to 10 parts by mass, preferably 0.01 to 1 part by mass, based on 100 parts by mass of the obtained compound of the formula (2).

[Applied reaction: Deprotection of the silane compound of the formula (1) or the siloxane compound of the formula (2) or (3)]
The organosilicon compound represented by the formula (1), (2) or (3) in the present invention is deprotected by adding a deprotecting agent when s in the formula (7') or (8') is 0. By reacting, an organosilicon compound having 1 carbon number in the linking group of the silicon atom and the amino group can be produced.

As the deprotecting agent used in the deprotection reaction, the amide group of the formula (7') or the imide group of the formula (8') in the compounds represented by the formulas (1) to (3) is converted into an amino group. It is not particularly limited as long as it can be used, and for example, Greens's Protective Groups in Organic Synthesis, 5th edition, pp. 1012-1014, 2014, John. Those described by John Wiley & Sons, INC. Can be used. Among these, it is preferable to use a primary amine compound.

The primary amine compound is not particularly limited as long as the reaction proceeds, and specific examples thereof include alkylamines such as methylamine, n-butylamine, hexylamine and octylamine, ethylenediamine, propylenediamine, diethylenetriamine and tri. Examples thereof include ethylene tetraamine and tetraethylene hexaamine.

The blending amount of the deprotecting agent is about 1 to 100 mol with respect to 1 mol of the amide group of the formula (7') or the imide group of the formula (8') in the compounds of the formulas (1) to (3). The amount may be any amount, preferably 1 to 50 mol, more preferably 1 to 20 mol.

As described above, according to the production method in the present invention, from the general-purpose silane compound represented by the formula (4) or the siloxane compound represented by the formula (5) or (6), the formulas (1) to (3). ) Can be efficiently and easily obtained.
The obtained organosilicon compounds represented by the formulas (1) to (3) have a carbon number of 1 in the linking group between the silicon atom and the amino group by performing a deprotection reaction using a primary amine. Certain organosilicon compounds can be provided.
The silane compound and siloxane compound thus obtained in which the linking group of the silicon atom and the amino group has one carbon atom utilize the high reactivity of the amino group due to the electronic effect of the adjacent silicon and the adsorptivity of the amino group. It is extremely useful because it can be suitably used for surface modification of fillers, resin modification, fiber treatment agents, paint additives, cosmetic raw materials, and the like.

Hereinafter, the present invention will be described in more detail with reference to Examples and Application Examples, but the present invention is not limited to the following Examples. Further, in the examples, unless otherwise specified, the reaction and storage of the product were carried out in a nitrogen atmosphere.
The NMR measurement was performed using Avance III 400 (manufactured by Brucker).
The GC measurement was performed using a 7890B (column: HP-5) (manufactured by Agilent) at 10 ° C./min from 80 ° C.
The average degree of polymerization was measured by ²⁹ Si-NMR analysis using ECX-500II (manufactured by JEOL Ltd.).

[Example 1] Production of both-terminal N-phthalimide-1-ethyl-modified dimethylpolysiloxane In a 100 mL separable flask containing a magnetic stirrer chip, a rhodium (II) octanoate dimer (manufactured by Tokyo Kasei Kogyo Co., Ltd.) 7. 6 mg, 20.01 g of dimethylpolysiloxane (average degree of polymerization 38) closed at both ends, and 5.01 g of toluene were added, a stirring blade and a cooler were attached, and the temperature was raised to 120 ° C. under a nitrogen atmosphere. Aged for time. The color of the solution changed from pale green to pale yellow. Next, a solution prepared by dissolving 2.49 g of N-vinylphthalimide (manufactured by Tokyo Chemical Industry Co., Ltd.) in 4.92 g of toluene was prepared in a dropping funnel and attached to the above reaction vessel. After cooling the reaction solution to 90 ° C., the reaction solution was added dropwise over 1.5 hours, and after the addition was completed, the reaction solution was aged at 90 ° C. for 3.5 hours.
A part of the sample was taken and ¹ H-NMR measurement was carried out, and it was confirmed that the signal of the hydrosilyl group had disappeared. Toluene was distilled off from the obtained solution with an evaporator (100 ° C., 10 torr or less), activated carbon (2.00 g) was added, the mixture was stirred at room temperature for 2 hours, and then pressure-filtered to obtain 14.73 g of pale yellow color. Obtained clear oil.

The ¹ H-NMR measurement result of the obtained compound is shown in FIG. From the quadruple wire at 3.73 ppm and the double wire at 1.37 ppm, it was suggested that the compound had the following structure added to the α-position of the vinyl group of N-vinylphthalimide.
^{1 1} H-NMR (CDCl ₃ , 400 MHz) δ: 7.81-7.75 (m, 4H), 7.68-7.63 (m, 4H), 3.73 (q, J = 7.7 Hz) , 2H), 1.37 (d, J = 7.7 Hz, 6H), 0.07.

（ｐ＝５２）

(P = 52)

[Example 2] Production of both-terminal N-phthalimide-1-ethyl-modified dimethylpolysiloxane In a 100 mL separable flask containing a magnetic stirrer chip, a rhodium (II) octanoate dimer (manufactured by Tokyo Kasei Kogyo Co., Ltd.) 7. Add 8 mg, 20.05 g of dimethylpolysiloxane (average degree of polymerization 8) with both ends dimethylhydrogensilyl group closed, and 5.00 g of toluene, attach a stirring blade and a cooler, raise the temperature to 120 ° C. in a nitrogen atmosphere, and 1 Aged for time. The color of the solution changed from pale green to pale yellow. Next, a solution prepared by dissolving 10.58 g of N-vinylphthalimide (manufactured by Tokyo Chemical Industry Co., Ltd.) in 22.43 g of toluene was prepared in a dropping funnel and attached to the above reaction vessel. After cooling the reaction solution to 100 ° C., the reaction solution was added dropwise over 3 hours, and after the addition was completed, the reaction solution was aged at 100 ° C. for 2 hours.
A part of the sample was taken and ¹ H-NMR measurement was carried out, and it was confirmed that the signal of the hydrosilyl group had disappeared. Toluene was distilled off from the obtained solution with an evaporator (100 ° C., 10 torr or less), activated carbon (2.00 g) was added, the mixture was stirred at room temperature for 2 hours, and then pressure-filtered to obtain 20.87 g of pale yellow. Obtained clear oil.

As a result of ¹ H-NMR measurement of the obtained compound, it was suggested from the quadruple wire of 3.73 ppm and the double wire of 1.37 ppm that the compound had the following structure added to the 1-position.
^{1 1} H-NMR (CDCl ₃ , 400 MHz) δ: 7.81-7.75 (m, 4H), 7.68-7.63 (m, 4H), 3.73 (q, J = 7.7 Hz) , 2H), 1.37 (d, J = 7.7 Hz, 6H), 0.07.

（ｐ＝１５）

(P = 15)

[Example 3] Production of 1,3-bis (N-acetamide-1-ethyl) -1,1,3,3-tetramethyldisiloxane In a 100 mL separable flask containing a magnetic stirrer chip and equipped with a cooler. , Octamate rhodium (II) dimer (manufactured by Tokyo Kasei Kogyo Co., Ltd.) 3.9 mg, 1,1,3,3-tetramethyldisiloxane 10.00 g, toluene 23.31 g, and 90 ° C. under a nitrogen atmosphere. The temperature was raised to. A solution prepared by dissolving 13.31 g of N-vinylacetamide (manufactured by Tokyo Chemical Industry Co., Ltd.) in 26.61 g of toluene was added dropwise thereto over 30 minutes, and then aged for 3 hours. A part of the sample was taken and GC measurement and ¹ H-NMR measurement were carried out, and it was confirmed that the signal of the raw material and the hydrosilyl group disappeared. Activated carbon (2.00 g) was added to the obtained solution, stirred at room temperature for 1 hour, pressure-filtered, and toluene was distilled off with an evaporator (80 ° C., 10 torr or less) to obtain 19.45 g of light. A yellow solid was obtained (yield 86%).

The ¹ H-NMR measurement result of the obtained compound is shown in FIG. From the integral ratio of the signals of 3.41 ppm and 1.13 ppm, it was shown that the following compound added to the α-position of the vinyl group of N-vinylacetamide was obtained. In addition, from the ¹³ C-NMR measurement results, two related peaks were confirmed by amide resonance. This suggests that the compound has the following structure.
^{1 1} H-NMR (CDCl ₃ , 400 MHz) δ: 6.19 (br, 2H), 3.46-3.35 (m, 2H), 2.00 (s, 6H), 1.14-1.08 (M, 6H), 0.08 (s, 12H).
¹³ C-NMR (CDCl ₃ , 100 MHz) δ: 169.9, 169.8, 36.3, 36.223.22, 23.1, 15.6, -1.3, -1.4, -1.9, -2.1.

[Example 4] Production of N-acetamide-1-ethyl-diethoxymethylsilane and poly (N-acetamido-1-ethyl) methylsiloxane Octane in a 100 mL separable flask containing a magnetic stirrer chip and equipped with a cooler. 7.8 mg of rhodium (II) acid dimer (manufactured by Tokyo Kasei Kogyo Co., Ltd.), 20.00 g of diethoxymethylsilane and 10.00 g of toluene were added, and the temperature was raised to 95 ° C. under a nitrogen atmosphere. A solution prepared by dissolving 13.31 g of N-vinylacetamide (manufactured by Tokyo Chemical Industry Co., Ltd.) in 26.61 g of toluene was added dropwise thereto over 30 minutes, and then aged for 3 hours. A part of the sample was taken and GC measurement was carried out, and it was confirmed that the signal of the hydrosilyl group of the raw material diethoxymethylsilane had disappeared. Then, distillation purification (boiling point: 122 ° C./2 to 3 mmHg) was carried out to obtain 9.00 g of a transparent liquid (yield 28%, GC purity> 99%).

The ¹ H-NMR measurement result of the obtained compound is shown in FIG. From the NMR measurement results, it was suggested that the compound had the following structure.
^{1 1} H-NMR (CDCl ₃ , 400 MHz) δ: 5.51 (br, 1H), 3.83-3.75 (m, 4H), 3.58-3.49 (m, 1H), 1.97 (S, 3H), 1.25-1.15 (m, 9H), 0.16 (s, 3H).
¹³ C-NMR (CDCl ₃ , 100 MHz) δ: 169.5,58.6, 33.5, 23.5, 18.3, 16.2, -6.5.

Next, put 7.69 g of the compound obtained above in a 100 mL three-necked flask equipped with a magnetic stirrer chip and a Dean-stark tube, slowly add 1.89 g of ion-exchanged water, and age for 2 hours. did. Then, 30.02 g of toluene was added, and the mixture was heated at 100 ° C. for 2 hours and dried at the same temperature under reduced pressure for 1 hour to obtain 4.38 g of a pale yellow solid product.

The ¹ H-NMR measurement result of the obtained compound is shown in FIG. In the above compound, the signals observed at 3.83-3.75 ppm and 1.25-1.21 ppm disappeared, suggesting that the compound is a linear compound having the following repeating units.
^{1 1} H-NMR (CDCl ₃ , 400 MHz) δ: 3.70-2.86 (br, 1H), 2.23-1.64 (br, 3H), 1.39-0.73 (br, 3H) , 0.37-0.16 (br, 3H).

[Example 5] Production of 3- (N-phthalimide-1-ethyl) -1,1,1,3,5,5,5-heptamethyltrisiloxane In a 100 mL separable flask containing a magnetic stirrer chip, octane Add 1.9 mg of rhodium (II) acid dimer (manufactured by Tokyo Chemical Industry Co., Ltd.), 1,1,1,3,5,5,5-heptamethyltrisiloxane 5.00 g, attach a cooler, and create a nitrogen atmosphere. The temperature was raised to 90 ° C. below. Next, a solution prepared by dissolving 4.63 g of N-vinylphthalimide (manufactured by Tokyo Chemical Industry Co., Ltd.) in 10.00 g of toluene was prepared in a dropping funnel, attached to the above reaction vessel, dropped over 2 hours, and dropped. After completion, it was aged at 90 ° C. for 5 hours. A part of the sample was taken and GC measurement was carried out, and it was confirmed that the signal of 1,1,1,3,5,5,5-heptamethyltrisiloxane as a raw material had disappeared. The obtained solution was pressure-filtered, and toluene was distilled off with an evaporator (100 ° C., 10 torr or less) to obtain 8.72 g of a pale yellow transparent oil (yield 90%, purity 89%).

The ¹ H-NMR measurement result of the obtained compound is shown in FIG. From the quadruple wire of 3.65 ppm and the double wire of 1.34 ppm, it was suggested that the compound had the following structure added to the α-position of the vinyl group of N-vinylphthalimide. Further, the amount of the compound added to the β-position of the vinyl group of the imide was <1% or less.
^{1 1} H-NMR (CDCl ₃ , 400 MHz) δ: 7.83-7.77 (m, 2H), 7.70-7.65 (m, 2H), 3.65 (q, J = 7.7 Hz) , 1H), 1.34 (d, J = 7.7 Hz, 3H), 0.28 (s, 3H), 0.12 (s, 9H), 0.05 (s, 9H).
¹³ C-NMR (CDCl ₃ , 100 MHz) δ: 168.6, 133.6, 132.4, 122.8, 36.4, 14.1, 1.8, 1.6, -1.0.

[Application Example 1] Production of 3- (1-aminoethyl) -1,1,1,3,5,5,5-heptamethyltrisiloxane In Example 5 in a 100 mL separable flask containing a magnetic stirrer chip. 7.40 g of the produced compound, 20.00 g of hexane and 7.80 g of ethylenediamine were added, a cooler was attached, the temperature was raised to 70 ° C. under a nitrogen atmosphere, and the mixture was aged for 3 hours. Then, after the stirring was stopped and the mixture was allowed to stand still, the upper layer of the phase-separated solution was recovered and distilled off with an evaporator (80 ° C., 10 torr or less) to obtain 1.96 g of pale yellow transparent oil (yield 39). %, GC purity 96%).

The ¹ H-NMR measurement result of the obtained compound is shown in FIG. From the quadruple wire at 2.14 ppm and the double wire at 1.09 ppm, it was suggested that the compound had the following structure with an amino group added at the 1-position.
^{1 1} H-NMR (CDCl ₃ , 400 MHz) δ: 2.14 (q, J = 7.4 Hz, 1H), 1.09 (d, J = 7.4 Hz, 3H), 1.09 (br, 2H), 0.10 (s, 18H), 0.05 (s, 3H).

Claims (5)

(A) The following formula (7) or (8)

(In formula (7), R'is a hydrogen atom, an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms and an aralkyl group having 7 to 20 carbon atoms. In the formulas (7) and (8), R "is independently a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms, and in the formula (8), X is unsubstituted. Alternatively, it is a divalent hydrocarbon group having 2 to 20 carbon atoms. In the formulas (7) and (8), s is 0 or 1 independently.)
And the compound represented by
(B) The following (b-1) or (b-2)
(B-1) Silane compound represented by the following formula (4)

(In the formula, R ² is a group selected from an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms and an aralkyl group having 7 to 20 carbon atoms, and R ³ is a group having 1 to 6 carbon atoms. It is a monovalent hydrocarbon group of. A is an integer of 1 to 3).
(B-2) A siloxane compound represented by the following formula (5) or (6)

(In formulas (5) and (6), R ⁵ is a group independently selected from a hydrogen atom, R ² and −OR ³ groups (R ² and R ³ are the same as described above). However, in each of the formulas (5) and (6), one or more of R ⁵ is a hydrogen atom. In the formula (5), m is a number of 0 to 1,000 and n is 0 to 200. M + n is a number from 0 to 1,200, and the arrangement of repeating units enclosed by m + n may be block or random. In equation (6), y is a positive number from 1 to 8. , Z is a number from 0 to 7, and y + z is a positive number from 3 to 8, and the arrangement of the repeating units enclosed by y + z may be block or random.)
An organosilicon compound having one or more hydrosilyl groups in one molecule represented by (c) is reacted in the presence of (c) a hydrosilylation reaction catalyst to form the formula (7) or (8) and the formula (4). Correspondingly, the compound represented by the following formula (1), the compound represented by the following formula (2) corresponding to the formula (7) or (8) and the formula (5), the formula (7) or (8). ) And the compound represented by the following formula (3) corresponding to the formula (6).

[In the equations (1) and (2), R ¹ is the following equation (7') or (8').

(In the formula, R', R ", X and s are the same as described above. The broken line indicates a bond with a silicon atom.)
In the formulas (2) and (3), R ⁴ is independently represented by R ¹ , R ² and −OR ³ groups (R ¹ to R ³ are the same as described above). The same applies hereinafter.), And R ^5'is a group independently selected from hydrogen atom, R ¹ , R ² and −OR ³ groups, respectively, and R ² in the formula (1), R ³ and a, m and n in formula (2), y and z in formula (3) are the same as above, but formulas (2) and (3) each have one or more R ^1s . Have. ]
A method for producing an organosilicon compound. (C) The method for producing an organosilicon compound according to claim 1, wherein the hydrosilylation reaction catalyst of the component is a rhodium compound. The method for producing an organic silicon compound according to claim 1 or 2, wherein the hydrosilylation reaction catalyst of the component (c) is a rhodium compound selected from rhodium carboxylate, cyclooctadiene rhodium chloride dimer and cyclooctadiene rhodium methoxydo dimer. Further, claim 1 includes a step of performing a polymerization reaction using an organosilicon compound represented by the formula (1), (2) or (3) produced by the method according to any one of claims 1 to 3. The method for producing an organosilicon compound according to any one of 3 to 3. The method for producing an organosilicon compound according to claim 4, wherein a polymerization catalyst is added in the polymerization reaction.

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