EP0247501A2
Expired / Lapsed
EP
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Method for preparing methacryloxy and acryloxy containing organosilanes and organosilicones
Assignee: OSI Specialties Inc
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Filing: 1987-05-19
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Granted: —
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Expires: 2007-05-19
Abstract
Abstract This invention relates to an improved process for preparing, purifying and/or storing methacryloxy or acryloxy containing organosilicon compounds without the undesirable polymerization normally associated with the methacrylate bonds. In an alternative embodiment, the process is even further improved with the addition of certain stabilizers, and in particular diketone or ketoester stabilizers.
Inventors
- 👤 Nan Shieh Chu
- 👤 Bernard Kanner
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-10-31 00:59
CPC Classifications
C; C08; C08G; C08G77/00; C08G77/04; C08G77/38; C07; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/18; C07F7/1804; C07F7/1872; C07F7/1876
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
204 words
A process for preparing methacryloxy or acryloxy containing organosilicon compounds without undesirable polymerization which process comprises: (a) charging a first reservoir with (i) 2-10% molar excess, preferably 3-5 molar excess of a methacryloxy or acryloxy functional containing compound over a stochiometric amount of alkoxysilane or Si-H containing silicone which would be needed to form a complete reaction between said functional containing compound and said organosilane or silicone; and (ii) 0.2 to 5.0% of an inhibitor by weight based on the amount of methacryloxy or acryloxy used; (b) charging a second reservoir with (i) a stochiometric amount of alkoxysilane or Si-H containing silicone needed to form a complete reaction with the methacryloxy or acryloxy containing compound employed in (a); and (ii) a catalytic amount of platinum-containing hydrosilation catalyst, preferably 2 - 100 ppm or 2 - 20 ppm; (c) combining the contents of the two reservoirs in a reactor vessel at 80-120°C or 90-120°C; (d) post treating the crude reaction product with 1-5%, preferably 1-3% alcohol by weight based on weight of product or post heating the reaction product for 5-40 minutes, preferably 20-30 minutes at 100-140°C or 110-130°C, and (e) vacuum distilling the post-treated product in the presence of inhibitors and under reduced pressure.
Claim 2
Dependent Claim
204 words
A process for preparing methacryloxy or acryloxy containing organosilicon compounds without undesirable polymerization which process comprises: (a) charging a first reservoir with (i) 2-10% molar excess, preferably 3-5 molar excess of a methacryloxy or acryloxy functional containing compound over a stochiometric amount of alkoxysilane or Si-H containing silicone which would be needed to form a complete reaction between said functional containing compound and said organosilane or silicone; and (ii) 0.2 to 5.0% of an inhibitor by weight based on the amount of methacryloxy or acryloxy used; (b) charging a second reservoir with (i) a stochiometric amount of alkoxysilane or Si-H containing silicone needed to form a complete reaction with the methacryloxy or acryloxy containing compound employed in (a); and (ii) a catalytic amount of platinum-containing hydrosilation catalyst, preferably 2 - 100 ppm or 2 - 20 ppm; (c) combining the contents of the two reservoirs in a reactor vessel at 80-120°C or 90-120°C; (d) post treating the crude reaction product with 1-5%, preferably 1-3% alcohol by weight based on weight of product or post heating the reaction product for 5-40 minutes, preferably 20-30 minutes at 100-140°C or 110-130°C, and (e) vacuum distilling the post-treated product in the presence of inhibitors and under reduced pressure.
Claim 3
Dependent Claim
41 words
The process of claim 1, characterized by charging the first reservoir with a stabilizer, vacuum distilling the product in the presence of inhibitors and under reduced pressure after combining the contents of the two reservoirs in a reactor vessel at 80-120°C.
Claim 4
Dependent Claim
39 words
The process of claim 1 or 2 wherein the alkoxysilane is represented by the general formula: Rʹ i(OR) 3-n wherein R and Rʹ are lower alkyl moiety containing 1-20 carbon atoms, preferably 1-4 carbon atoms and n is 0-1.
Claim 5
Dependent Claim
59 words
The process of claim 1 or 2 wherein the Si-H containing silicone is a polysiloxane polymer with the general formula: where Rʺ is a lower alkyl group having 1 to 8 carbons or an aryl group having 6 to 10 carbons, preferably a methyl group and x ranges from 0 to 100 and y ranges from 1 to 30.
Claim 6
Dependent Claim
67 words
The process of claims 1 to 4 wherein the methacryloxy or acryloxy functional containing compound is represented by the general formula: wherein R² is hydrogen, a lower alkyl group having 2 to 8 carbons or an aryl group having 6 to 10 carbons, X is CH₂CH₂O or a CH₂ or a combination of the two group, and m equals 0 to 10, preferably equals 0 to 5.
Claim 7
Dependent Claim
23 words
The process of claims 1 to 5 wherein the inhibitor is selected from phenolic inhibitors, aromatic amines, aromatic sulfur compounds and combinations thereof.
Claim 8
Dependent Claim
21 words
The process of claim 6 wherein the inhibitor is monomethyl ether of hydroquinone, Isonox™ 129 or Ionol or diphenylendiamine or phenothiazine.
Claim 9
Dependent Claim
16 words
The process of claims 1 to 7 wherein an inhibitor is used in the post-treatment step.
Claim 10
Dependent Claim
23 words
The process of claims 1 to 8 wherein the platinum-containing hydrosilation catalyst is selected from supported platinum catalysts and homogeneous soluble platinum complexes.
Claim 11
Dependent Claim
36 words
The process of claim 9 wherein the supported platinum catalyst is platinum on γ-alumina or charcoal and the homogenous soluble platinum complex is selected from chloroplatinic acid, bis-(ethylene platinous)chloride, dichlorobis(acetonitrile)platinum (II), cis-dichlorobis(triphenylphosphine)platinum (II) and tetrakis(tetraphenylphosphine)platinum (O).
Claim 12
Dependent Claim
21 words
The process of claim 10 wherein the soluble platinum complexes are used as solution in solvents, preferably isopropanol, acetonitrile or 1,2-dimethoxyethane.
Claim 13
Dependent Claim
23 words
The process of claims 2 to 11 wherein the stabilizer is selected from diketones and ketoesters, preferably pentadione-2,4 or hexadione-2,5 or methyl acetoacetate.
Claim 14
Dependent Claim
24 words
The process of claim 12 wherein the stabilizer is additionally a mono keto or ester containing compound, preferably mesityl oxide, pentanone-2 or methyl propionate.
References Cited (Backward Citations)
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