Method for producing (meth)acryloxy group-containing organosilicon compounds

Patent metadata

Field	Value
Publication number	US-12371447-B2
Application number	US-202217963549-A
Country	US
Kind code	B2
Filing date	Oct 11, 2022
Priority date	Oct 28, 2021
Publication date	Jul 29, 2025
Grant date	Jul 29, 2025

Abstract

An acryloxy or methacryloxy group-containing organosilicon compound of the formula

(wherein R 1 is a substituted or unsubstituted monovalent hydrocarbon group of 1 to 10 carbon atoms, R 2 is a hydrogen atom or a methyl group, R 3 is an unsubstituted divalent hydrocarbon group of 1 to 18 carbon atoms, X is a halogen atom and n is an integer of 1, 2 or 3) is to prepared by subjecting a hydrohalosilane compound of the formula

HSiX n R 1 3-n   ( 1 )

and an alkenyl group-containing (meth)acrylate compound of the formula

to a hydrosilylation reaction in the presence of an acid amide compound and a platinum catalyst. This method is able to suppress, in the industrial scale production of (meth)acryloyloxy group-containing organosilicon compounds, propagation reactions by which the starting (meth)acrylate compound self-polymerizes.

First claim

The invention claimed is:

1. A method for preparing an acryloxy or methacryloxy group-containing organosilicon compound of general formula (3) below

wherein R 1 is a substituted or unsubstituted monovalent hydrocarbon group of 1 to 10 carbon atoms, R 2 is a hydrogen atom or a methyl group, R 3 is an unsubstituted divalent hydrocarbon group of 1 to 18 carbon atoms, X is a halogen atom and n is an integer of 1, 2 or 3, which method comprises the step of subjecting a hydrohalosilane compound of general formula (1) below
HSiX n R 1 3-n   (1)

wherein R 1 , X and n are as defined above and an alkenyl group-containing (meth)acrylate compound of general formula (2) below

wherein R 2 and R 3 are as defined above to a hydrosilylation reaction in the presence of an acid amide compound and a platinum catalyst.

2. The method of claim 1 , wherein the acid amide compound is an acid amide compound of general formula (4) below
R 4 —[C(═O)—NR 5 2 ] k   (4)

wherein R 4 is a hydrogen atom or a substituted or unsubstituted k-valent hydrocarbon group of 1 to 30 carbon atoms, each R 5 is independently a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group of 1 to 30 carbon atoms, and k is the integer 1 or 2, with the proviso that the acid amide compound of general formula (4) does not contain a primary acid amide compound of general formula (5) below
R 6 —C(═O)—NH 2   (5)

wherein R 6 is a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group of 1 to 30 carbon atoms.

3. The method of 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.

4. The method of claim 1 , wherein the hydrosilylation reaction is carried out in the presence of a polymerization inhibitor.

5. The method of claim 4 , wherein the polymerization inhibitor is a phenolic polymerization inhibitor or a hindered phenolic polymerization inhibitor.

6. The method of claim 5 . wherein the phenolic 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 of claim 5 , wherein the hindered phenolic 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 benzopyran-6-ol.

Assignees

• Shinetsu Chemical Co

Inventors

• Nyuugaku Takeshi

Classifications

• C07F7/122

  by reactions involving the formation of Si-C linkages (hydrosilylation reactions C07F7/14; direct synthesis C07F7/16) · CPC title

• C07F7/14 Primary

  Preparation thereof from {optionally substituted} halogenated silanes and hydrocarbons {hydrosilylation reactions} · CPC title