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US5371262A Expired / Lapsed US ⏱️ 0.0 years remaining

Hydroxymethyltrialkoxysilanes and methods of making and using the same

Assignee: Gelest Inc
•
Filing: 1993-03-10
•
Granted: 1994-12-06
•
Expires: 2013-03-10
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Abstract

Abstract Novel hydroxymethyltrialkoxysilanes of the formula: <IMAGE> (I) are produced by transesterifying a carboxylic acid ester of hydroxymethyltrialkoxysilane with an alcohol, and distilling the reaction mixture to remove the carboxylate of the alcohol. The carboxylic acid ester of hydroxymethyltrialkoxysilane is prepared by the reaction of an alkali metal carboxylate with chloromethyltrialkoxysilane, which in turn is prepared by the reaction of a trialkylorthoester with chloromethyltrichlorosilane by heating to reflux with removal of alkylchloride, followed by distillation to remove alkyl ester. The hydroxymethyltrialkoxysilanes and carboxylic acid esters thereof, as well as carboxymethyltrialkoxysilanes, are particularly useful in sol-gel processing by undergoing hydrolysis to yield hydroxymethylsilanetriol, and subsequent hydrolysis and polycondensation products.

Inventors

  • 👤 Barry C. Arkles

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-04 19:34
CPC Classifications
C; C08; C08G; C08G77/00; C08G77/60; C03; C03C; C03C1/00; C03C1/006; C03C1/008; C07; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/18; C07F7/1804; C08G77/48; C08G77/50; C09; C09D; C09D183/00; C09D183/14

Claims Analysis

Total Claims: 13
Claim 1
Independent Claim 18 words
A hydroxymethyltrialkoxysilane of the formula: ##STR15## where R is an alkyl group and n is at least one.
Claim 2
Dependent Claim 18 words
A hydroxymethyltrialkoxysilane of the formula: ##STR15## where R is an alkyl group and n is at least one.
Claim 3
Dependent Claim 21 words
A hydroxymethyltrialkoxysilane according to claim 1 where R is a C 1 to C 3 alkyl group and n=1 to 100.
Claim 4
Dependent Claim 12 words
A hydroxymethyltrialkoxysilane according to claim 1 where R is a methyl group.
Claim 5
Dependent Claim 12 words
A hydroxymethyltrialkoxysilane according to claim 1 where R is an ethyl group.
Claim 6
Dependent Claim 12 words
A hydrolysis reaction product of a hydroxymethyltrialkoxysilane wherein said product comprises hydroxymethylsilanetriol.
Claim 7
Dependent Claim 12 words
A hydrolysis reaction product of a hydroxymethyltrialkoxysilane wherein said product comprises hydroxymethylsilanetriol.
Claim 8
Independent Claim 29 words
A method of producing a hydroxymethyltrialkoxysilane comprising transesterifying a carboxylic acid ester of hydroxymethyltrialkoxysilane with an alcohol, and distilling the reaction mixture to remove the carboxylate of the alcohol.
Claim 9
Independent Claim 29 words
A method of producing a hydroxymethyltrialkoxysilane comprising transesterifying a carboxylic acid ester of hydroxymethyltrialkoxysilane with an alcohol, and distilling the reaction mixture to remove the carboxylate of the alcohol.
Claim 10
Dependent Claim 37 words
A method according to claim 6 wherein said transesterification is carried out in the presence of sulfuric acid, and said alcohol has the same alkyl radical as the alkoxy group of said carboxylic acid ester of hydroxymethyltrialkoxysilane.
Claim 11
Dependent Claim 24 words
A method according to claim 6 wherein said carboxylic acid ester of hydroxymethyltrialkoxysilane is prepared by reaction of an alkali metal carboxylate with chloromethyltrialkoxysilane.
Claim 12
Dependent Claim 23 words
A method according to claim 8 wherein said carboxylate reaction is carried out in the presence of an acetonitrile solvent and 18-crown-6 catalyst.
Claim 13
Dependent Claim 35 words
A method according to claim 8 wherein said chloromethyltrialkoxysilane is prepared by reaction of an alcohol or trialkylorthoester with chloromethyltrichlorosilane by heating to reflux with removal of alkyl chloride, followed by distillation to remove alkylester.

References Cited (Backward Citations)

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