US4946977A
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US
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Method for the preparation of organosilanes containing methacryloxy or acryloxy groups
Assignee: Evonik Operations GmbH
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Filing: 1988-09-19
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Granted: 1990-08-07
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Expires: 2008-09-19
Abstract
Abstract The present invention is in the preparation of methacrylic or acryloxyalkylalkoxysilanes by the reaction at a temperature of from 80° and 130° C. of an alkali (meth) acrylate with a halogen alkylalkoxysilane in the presence of a quaternary ammonium salt which has long-chin alkyl moieties, in which the sum of all carbon atoms is between 10 and 40 as a phase-transfer catalyst. In the new procedure no solvents need to be used. The yields are better than 95%.
Inventors
- 👤 Gunther Bernhardt
- 👤 Jurgen Amort
- 👤 Margret Haas
- 👤 Horst Hanisch
- 👤 Heinz Kragl
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 23:20
CPC Classifications
C; C07; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/18; C07F7/1804; C07F7/1872; C07F7/1892
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
193 words
A method for the preparation of an organosilane containing a methacryloxy or an acryloxy group, of the general Formula I ##STR6## in which R 1 is a hydrogen atom or a methyl group, R 2 an alkyl moiety of 1 to 4 carbon atoms, R 3 an alkyl group with to 4 carbon atoms, or an alkoxyalkyl group with a total of 2 to 4 carbon atoms, m represents 0 or 1 or 2, and n represents 1, 3 or 4, comprising: reacting at a temperature of from 80 to 130° C. an alkali methacrylate or acrylate with a halogen alkylsilane of the general Formula II ##STR7## in which R 2 , R 3 , m and n are as defined above and Hal represents, chlorine or bromine, in the presence of a catalyst being a quaternary ammonium salt of the general Formula III ##STR8## in which Y.sup.(-) is a halide ion, sulfate ion or phosphate ion and R 4 , R 5 , R 6 and R 7 are identical or different alkyl groups with 1 to 37 carbon atoms, the sum of all carbon atoms amounting to between 10 and 40.
Claim 2
Independent Claim
193 words
A method for the preparation of an organosilane containing a methacryloxy or an acryloxy group, of the general Formula I ##STR6## in which R 1 is a hydrogen atom or a methyl group, R 2 an alkyl moiety of 1 to 4 carbon atoms, R 3 an alkyl group with to 4 carbon atoms, or an alkoxyalkyl group with a total of 2 to 4 carbon atoms, m represents 0 or 1 or 2, and n represents 1, 3 or 4, comprising: reacting at a temperature of from 80 to 130° C. an alkali methacrylate or acrylate with a halogen alkylsilane of the general Formula II ##STR7## in which R 2 , R 3 , m and n are as defined above and Hal represents, chlorine or bromine, in the presence of a catalyst being a quaternary ammonium salt of the general Formula III ##STR8## in which Y.sup.(-) is a halide ion, sulfate ion or phosphate ion and R 4 , R 5 , R 6 and R 7 are identical or different alkyl groups with 1 to 37 carbon atoms, the sum of all carbon atoms amounting to between 10 and 40.
Claim 3
Dependent Claim
18 words
The method of claim 1 wherein the quaternary ammonium salt is tris(n-C 8 -and C 10 -alkyl)methylammonium chloride.
Claim 4
Dependent Claim
17 words
The method of claim 1 wherein the reaction is performed in the absence of an additional solvent.
Claim 5
Dependent Claim
28 words
The method of claim 1 wherein the molar ratio of the input alkali methacrylate or acrylate to the halogen alkylsilane of Formula II is between 1.2:1 and 1:1.2.
Claim 6
Dependent Claim
19 words
The method of claim 1 wherein the reaction is conducted at a temperature of from 100 to 120° C.
Claim 7
Dependent Claim
25 words
The method of claim 1 wherein the catalyst is used in an amount of 0.001 to 0.05 mole per mole of alkali methacrylate or acrylate.
Claim 8
Dependent Claim
25 words
The method to claim 1 wherein the catalyst is used in an amount of 0.005 to 0.03 moles per mole of alkali methacrylate or acrylate.
Claim 9
Dependent Claim
58 words
The method of claim 1 wherein the catalyst is selected from one or more of the group consisting of tributyl methyl ammonium chloride, triethylcetyl ammonium bromide, didodecyl dimethyl ammonium chloride, distearyl dimethyl ammonium chloride, tricaprylmethyl ammonium chloride, ALIQUAT.sup.(R) 336 (tris(n-C 8 -and C 10 -alkyl)methyl ammonium chloride), trioctyl methyl ammonium chloride, tetrabutyl ammonium chloride or tetrabutyl ammonium bromide.
Claim 10
Dependent Claim
19 words
The method of claim 1 wherein the alkali methacrylate or alkali acrylate is a salt of sodium or potassium.
Claim 11
Dependent Claim
27 words
The method of claim 1 wherein the halogen alkylsilane is selected from the group consisting of chloromethyldimethylmethoxysilane, γ-chloropropyltrimethoxysilane; γ-chloropropyltriethoxysilane; γ-chloropropyltris(methoxyethoxy)silane; γ-chloropropylmethyldimethoxysilane; γ-chloropropylbutyldimethoxysilane; δ-chlorobutyltrimethoxysilane; δ-chlorobutylmethyldimethoxysilane; δ-chlorobutyltris(methoxyethoxy)silane; and γ-bromopropyltrimethoxysilane.
Claim 12
Dependent Claim
16 words
The method of claim 1 wherein polymerization is inhibited by the addition of a polymerization inhibitor.
Claim 13
Dependent Claim
23 words
The method of claim 11 wherein the polymerization inhibitor is selected from the group consisting of hydroquinone, hydroquinone monomethyl ether, N,N'-diphenyl-p-phenylenediamine, and phenyl-α-naphthylamine.
Claim 14
Dependent Claim
26 words
The method of claim 11 wherein the polymerization inhibitor is used in an amount of 0.001 to 1 wt.-% of the organosilane of the Formula I.
Claim 15
Dependent Claim
18 words
The method of claim 1 wherein the methacrylate or acrylate is used in the form of a solution.
Claim 16
Dependent Claim
18 words
The method of claim 1 wherein the methacrylate or acrylate is used in the form of a dispersion.
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1993-08-06 | 1994-02-05 | 1994-08-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-08-06 | 1998-02-05 | 1998-08-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-08-06 | 2002-02-05 | 2002-08-07 | $7700.00 | Window Closed / Lapsed |