US4709067A
Expired / Lapsed
US
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Method for preparing methacryloxy and acryloxy containing organosilanes and organosilicones
Assignee: General Electric Co
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Filing: 1986-05-20
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Granted: 1987-11-24
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Expires: 2006-05-20
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 S. Chu
- 👤 Bernard Kanner
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 14:10
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: 79
Claim 1
Independent Claim
183 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 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; (c) combining the contents of the two reservoirs in a reactor vessel at 80°-120° centigrade. (d) post treating the crude reaction product with 1-5% alcohol by weight based on weight of product or post heating the reaction product for 5-40 minutes at 100°-140° C.; and (e) vacuum distilling the post-treated product in the presence of inhibitors and under reduced pressure.
Claim 2
Dependent Claim
183 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 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; (c) combining the contents of the two reservoirs in a reactor vessel at 80°-120° centigrade. (d) post treating the crude reaction product with 1-5% alcohol by weight based on weight of product or post heating the reaction product for 5-40 minutes at 100°-140° C.; and (e) vacuum distilling the post-treated product in the presence of inhibitors and under reduced pressure.
Claim 3
Dependent Claim
161 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 to 10% 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; (ii) 0.2 to 5.0% of an inhibitor by weight based on the amount of methacryloxy or acryloxy used; and (iii) a stabilizer; (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; (c) combining the contents of the two reservoirs in a reactor vessel at 80° to 120° centigrade; and (d) vacuum distilling the product in the presence of inhibitors and under reduced pressure.
Claim 4
Dependent Claim
161 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 to 10% 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; (ii) 0.2 to 5.0% of an inhibitor by weight based on the amount of methacryloxy or acryloxy used; and (iii) a stabilizer; (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; (c) combining the contents of the two reservoirs in a reactor vessel at 80° to 120° centigrade; and (d) vacuum distilling the product in the presence of inhibitors and under reduced pressure.
Claim 5
Dependent Claim
31 words
The process of claim 1 wherein the alkoxysilane is represented by the general formula: ##STR4## wherein R and R' are lower alkyl moiety containing 1-20 carbon atoms and n is 0-1.
Claim 6
Dependent Claim
14 words
The process of claim 3 where the lower alkyl moiety contains 1-4 carbon atom.
Claim 7
Dependent Claim
53 words
The process of claim 1 wherein the Si--H containing silicone is a polysiloxane polymer with the general formula: ##STR5## where R is a lower alkyl group having 1 to 8 carbons or an aryl group having 6 to 10 carbons, x ranges from 0 to 100 and y ranges from 1 to 30.
Claim 8
Dependent Claim
9 words
The process of claim 5 wherein R is methyl.
Claim 9
Dependent Claim
67 words
The process of claim 1 wherein the methacryloxy or acryloxy functional containing compound is represented by the general formula: ##STR6## wherein R 2 is hydrogen, a lower alkyl group having 2 to 8 carbons or an aryl group having 6 to 10 carbons, X is CH 2 CH 2 O or a CH 2 or a combination of the two groups, and m equals 0 to 10.
Claim 10
Dependent Claim
11 words
The process of claim 7 wherein m eguals 0 to 5.
Claim 11
Dependent Claim
25 words
The process of claim 1 wherein the inhibitor is selected from the group consisting of phenolic inhibitors, aromatic amines, aromatic sulfur compounds and combinations thereof.
Claim 12
Dependent Claim
18 words
The process of claim 9 wherein the phenolic inhibitor is monomethyl ether of hydroquinone, Isonox™ 129 or Ionol.
Claim 13
Dependent Claim
11 words
The process of claim 9 wherein the aromatic amine is diphenylenediamine.
Claim 14
Dependent Claim
13 words
The process of claim 9 wherein the aroma is sulfur compound is phenothiazine.
Claim 15
Dependent Claim
15 words
The process of claim 1 wherein an inhibitor is used in the post treatment step.
Claim 16
Dependent Claim
25 words
The process of claim 13 wherein the inhibitor is selected from the group consisting of phenolic inhibitors, aromatic amines, aromatic sulfur compounds and combinations thereof.
Claim 17
Dependent Claim
18 words
The process of claim 14 wherein the phenolic inhibitor is monomethyl ether of hydroquinone, Isonox™ 129 or Ionol.
Claim 18
Dependent Claim
11 words
The process of claim 14 wherein the aromatic amine is diphenylenediamine.
Claim 19
Dependent Claim
12 words
The process of claim 14 wherein the aromatic sulfur compound is phenothiazine.
Claim 20
Dependent Claim
26 words
The process of claim 1 wherein the platinum containing hydrosilation catalyst is selected from the group consisting of supported platinum catalysts and homogeneous soluble platinum complexes.
Claim 21
Dependent Claim
16 words
The process of claim 11 wherein the supported platinum catalyst is platinum on γ-alumina or charcoal.
Claim 22
Dependent Claim
30 words
The process of claim 18 wherein the homogenous soluble platinum complex is selected from the group consisting of chloroplatinic acid, bis-(ethylene platinous)chloride, dichlorobis(acetonitrile)platinum (II), cis-dichlorobis(triphenylphosphine) platinum (II) and tetrakis(tetraphenylphosphine)platinum (O).
Claim 23
Dependent Claim
16 words
The process of claim 20 wherein the soluble platinum complexes are used as solutions in solvents.
Claim 24
Dependent Claim
14 words
The process of claim 21 wherein the solvents are isopropanol, acetonitrile or 1,2 dimethoxyethane.
Claim 25
Dependent Claim
15 words
The process of claim 1 wherein the first reservoir is additionally charged with a stabilizer.
Claim 26
Dependent Claim
31 words
The process of claim 2 wherein the alkoxysilane is represented by the general formula: ##STR7## wherein R and R' are lower alkyl moiety containing 1-20 carbon atoms and n is 0-1.
Claim 27
Dependent Claim
14 words
The process of claim 24 where the lower alkyl moiety contains 1-4 carbon atom.
Claim 28
Dependent Claim
53 words
The process of claim 2 wherein the Si--H containing silicone is a polysiloxane polymer with the general formula: ##STR8## where R is a lower alkyl group having 1 to 8 carbons or an aryl group having 6 to 10 carbons, x ranges from 0 to 100 and y ranges from 1 to 30.
Claim 29
Dependent Claim
9 words
The process of claim 26 where R is methyl.
Claim 30
Dependent Claim
67 words
The process of claim 2 wherein the methacryloxy or acryloxy functional containing compound is represented by the general formula: ##STR9## wherein R 2 is hydrogen, a lower alkyl group having 2 to 8 carbons or an aryl group having 6 to 10 carbons, X is CH 2 CH 2 O or a CH 2 or a combination of the two groups, and m equals 0 to 10.
Claim 31
Dependent Claim
11 words
The process of claim 28 wherein m equals 0 to 5.
Claim 32
Dependent Claim
25 words
The process of claim 2 wherein the inhibitor is selected from the group consisting of phenolic inhibitors, aromatic amines, aromatic sulfur compounds and combinations thereof.
Claim 33
Dependent Claim
18 words
The process of claim 30 wherein the phenolic inhibitor is monomethyl ether of hydroquinone, Isonox™ 129 or Ionol.
Claim 34
Dependent Claim
11 words
The process of claim 30 wherein the aromatic amine is diphenylenediamine.
Claim 35
Dependent Claim
12 words
The process of claim 30 wherein the aromatic sulfur compound is phenothiazine.
Claim 36
Dependent Claim
15 words
The process of claim 2 wherein a inhibitor is used in the post treatment step.
Claim 37
Dependent Claim
25 words
The process of claim 34 wherein the inhibitor is selected from the group consisting of phenolic inhibitors, aromatic amines, aromatic sulfur compounds and combinations thereof.
Claim 38
Dependent Claim
17 words
The process of claim 35 wherein the phenolic inhibitor is monomethyl of hydroquinone, Isonox™ 129 or Ionol.
Claim 39
Dependent Claim
11 words
The process of claim 35 wherein the aromatic amine is diphenylenediamine.
Claim 40
Dependent Claim
12 words
The process of claim 35 wherein the aromatic sulfur compound is phenothiazine.
Claim 41
Dependent Claim
26 words
The process of claim 2 wherein the platinum containing hydrosilation catalyst is selected from the group consisting of supported platinum catalysts and homogeneous soluble platinum complexes.
Claim 42
Dependent Claim
16 words
The process of claim 39 wherein the supported platinum catalyst is platinum on γ-alumina or charcoal.
Claim 43
Dependent Claim
30 words
The process of claim 39 wherein the homogeneous soluble platinum complex is selected from the group consisting of chloroplatinic acid, bis-(ethylene platinous)chloride, dichlorobis(acetonitrile)platinum (II), cis-dichlorobis(triphenylphosphine) platinum (II) and tetrakis(tetraphenylphosphine)platinum (O).
Claim 44
Dependent Claim
16 words
The process of claim 41 wherein the soluble platinum complexes are used as solution in solvents.
Claim 45
Dependent Claim
14 words
The process of claim 42 wherein the solvents are isopropanol, acetonitrile or 1,2 dimethoxyethane.
Claim 46
Dependent Claim
18 words
The process of claim 2 wherein the stabilizer is selected from the group consisting of diketones and ketoesters.
Claim 47
Dependent Claim
14 words
The process of claim 44 wherein the diketone is pentadione- 2,4 or hexadione- 2,5.
Claim 48
Dependent Claim
11 words
The process of claim 44 wherein the ketoester is methyl acetoacetate.
Claim 49
Dependent Claim
17 words
The process of claim 44 wherein the stabilizer is additionally a mono keto or ester containing compound.
Claim 50
Dependent Claim
20 words
The process of claim 47 wherein the mono keto or ester containing compound is mesityl oxide, pentanone-2 or methyl proprionate.
Claim 51
Dependent Claim
326 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 of a methacryloxy or acryloxy functional containing compound ##STR10## wherein R 2 is hydrogen, a lower alkyl group having 2 to 8 carbons or an aryl group having 6 to 10 carbons, X is CH 2 CH 2 O or a CH 2 or a combination of the two groups, and m is egual to 0 to 10 which excess is 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% monomethyl ether of hydroquinone, Isonox™ 129 or Ionol by weight based on the amount of methacryloxy or acryloxy used; (b) charging a second reservoir with (i) a stochiometric amount of an alkoxysilane ##STR11## where R and R' are lower alkyl moiety containing 1 to 20 carbon atoms and n is 0 to 1 or a stochiometric amount of an Si--H containing silicone ##STR12## where R is a lower alkyl group having 1 to 8 carbons or an aryl group having 6 to 10 carbons, x ranges from 0 to 100 and y ranges from 1 to 30 which alkoxysilane or Si--H containing silicone is 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 selected from the group consisting of supported platinum catalysts and soluble platinum complexes; (c) combining the contents of the two reservoirs in a reactor vessel at 80°-120° centigrade; (d) post treating the crude reaction product with 1-5% alcohol by weight based on weight of product or post heating the reaction product for 5-40 minutes at 100°-140° C.; and (e) vacuum distilling the post treated product in the presence of phenolic or nonphenolic inhibitors under reduced pressure.
Claim 52
Dependent Claim
326 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 of a methacryloxy or acryloxy functional containing compound ##STR10## wherein R 2 is hydrogen, a lower alkyl group having 2 to 8 carbons or an aryl group having 6 to 10 carbons, X is CH 2 CH 2 O or a CH 2 or a combination of the two groups, and m is egual to 0 to 10 which excess is 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% monomethyl ether of hydroquinone, Isonox™ 129 or Ionol by weight based on the amount of methacryloxy or acryloxy used; (b) charging a second reservoir with (i) a stochiometric amount of an alkoxysilane ##STR11## where R and R' are lower alkyl moiety containing 1 to 20 carbon atoms and n is 0 to 1 or a stochiometric amount of an Si--H containing silicone ##STR12## where R is a lower alkyl group having 1 to 8 carbons or an aryl group having 6 to 10 carbons, x ranges from 0 to 100 and y ranges from 1 to 30 which alkoxysilane or Si--H containing silicone is 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 selected from the group consisting of supported platinum catalysts and soluble platinum complexes; (c) combining the contents of the two reservoirs in a reactor vessel at 80°-120° centigrade; (d) post treating the crude reaction product with 1-5% alcohol by weight based on weight of product or post heating the reaction product for 5-40 minutes at 100°-140° C.; and (e) vacuum distilling the post treated product in the presence of phenolic or nonphenolic inhibitors under reduced pressure.
Claim 53
Dependent Claim
295 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 of a methacryloxy or acryloxy functional containing compound ##STR13## wherein R 2 is hydrogen, a lower alkyl group having 2 to 8 carbons or an aryl group having 6 to 10 carbons, X is CH 2 CH 2 O or a CH 2 or a combination of the two groups, and m is egual to 0 to 10 which excess is 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; (ii) 0.2 to 5.0% monomethyl ether of hydroquinone, Isonox 129 or Ionol by weight based on the amount of methacryloxy or acryloxy used; and (iii) stabilizer; (b) charging a second reservoir with (i) a stochiometric amount of an alkoxysilane ##STR14## wherein R and R' are lower alkyl moiety containing 1 to 20 carbon atoms and n is 0 to 1 or a stochiometric amount of Si--H containing silicone ##STR15## where R is a lower alkyl group having 1 to 8 carbons or an aryl group having 6 to 10 carbons, x ranges from 0 to 100 and y ranges 1 to 30 which alkoxysilane or Si--H containing silicone is 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 selected from the group consisting of supported platinum catalysts and soluble platinum complexes; (c) combining the contents of the two reservoirs in a reactor vessel at 80°-120° centigrade; and (d) vacuum distilling the product in the presence of phenolic or nonphenolic inhibitors under reduced pressure.
Claim 54
Dependent Claim
295 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 of a methacryloxy or acryloxy functional containing compound ##STR13## wherein R 2 is hydrogen, a lower alkyl group having 2 to 8 carbons or an aryl group having 6 to 10 carbons, X is CH 2 CH 2 O or a CH 2 or a combination of the two groups, and m is egual to 0 to 10 which excess is 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; (ii) 0.2 to 5.0% monomethyl ether of hydroquinone, Isonox 129 or Ionol by weight based on the amount of methacryloxy or acryloxy used; and (iii) stabilizer; (b) charging a second reservoir with (i) a stochiometric amount of an alkoxysilane ##STR14## wherein R and R' are lower alkyl moiety containing 1 to 20 carbon atoms and n is 0 to 1 or a stochiometric amount of Si--H containing silicone ##STR15## where R is a lower alkyl group having 1 to 8 carbons or an aryl group having 6 to 10 carbons, x ranges from 0 to 100 and y ranges 1 to 30 which alkoxysilane or Si--H containing silicone is 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 selected from the group consisting of supported platinum catalysts and soluble platinum complexes; (c) combining the contents of the two reservoirs in a reactor vessel at 80°-120° centigrade; and (d) vacuum distilling the product in the presence of phenolic or nonphenolic inhibitors under reduced pressure.
Claim 55
Dependent Claim
18 words
The process of claim 50 wherein the stabilizer is selected from the group consisting of diketones and ketoesters.
Claim 56
Dependent Claim
13 words
The process of claim 50 wherein the diketone is pentadione- 2,4 or hexadione-2,5.
Claim 57
Dependent Claim
11 words
The process of claim 50 wherein the ketoester is methyl acetoacetate.
Claim 58
Dependent Claim
17 words
The process of claim 51 wherein the stabilizer is additionally a mono keto or ester containing compound.
Claim 59
Dependent Claim
21 words
The process of claim 54 wherein the mono keto or ester containing compound is mesityl oxide, pentanone- 2 or methyl proprionate.
Claim 60
Dependent Claim
285 words
A process for preparin methacryloxy or acryloxy containin organosilicon compounds without undesirable polymerization which process comprises: (a) charging a first reservoir with (i) 3-5% molar excess of a methacryloxy or acryloxy functional containing compound ##STR16## wherein R" is hydrogen, a lower alkyl group having 2 to 8 carbons or an aryl group having 6 to 10 carbons, X is CH 2 CH 2 O or a CH 2 or a combination of the two groups, 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) 0.5 to 2.0% monomethyl ether of hydroguinone, phenothiazine, or diphenylenediamine inhibitor by weight based on the amount of methacryloxy or acryloxy used; (b) charging a second reservoir with (i) a stochiometric amount of alkoxysilane ##STR17## wherein R and R' are lower alkyl moiety containing 1 to 4 carbons and n is 0 to 1 or a stochiometric amount of an Si--H containing silicone ##STR18## where x ranges from 0 to 100 and y ranges from 1 to 30 which alkoxysilane or Si--H containing silicone is needed to form a complete reaction with a given methacryloxy or acryloxy containing compound and (ii) 2 to 20 parts per million of platinum on Y-alumina or charcoal; (c) combining the contents of the two reservoirs in a reactor vessel at 80°-120° centigrade; (d) post treating the crude reaction product with 1-3% alcohol by weight based on weight of product or post heating the reaction product for 20-30 minutes at 100°-140° C.; and (e) vacuum distilling the post treated product in the presence of phenolic or nonphenolic inhibitors or diphenylenediamine and under reduced pressure.
Claim 61
Dependent Claim
285 words
A process for preparin methacryloxy or acryloxy containin organosilicon compounds without undesirable polymerization which process comprises: (a) charging a first reservoir with (i) 3-5% molar excess of a methacryloxy or acryloxy functional containing compound ##STR16## wherein R" is hydrogen, a lower alkyl group having 2 to 8 carbons or an aryl group having 6 to 10 carbons, X is CH 2 CH 2 O or a CH 2 or a combination of the two groups, 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) 0.5 to 2.0% monomethyl ether of hydroguinone, phenothiazine, or diphenylenediamine inhibitor by weight based on the amount of methacryloxy or acryloxy used; (b) charging a second reservoir with (i) a stochiometric amount of alkoxysilane ##STR17## wherein R and R' are lower alkyl moiety containing 1 to 4 carbons and n is 0 to 1 or a stochiometric amount of an Si--H containing silicone ##STR18## where x ranges from 0 to 100 and y ranges from 1 to 30 which alkoxysilane or Si--H containing silicone is needed to form a complete reaction with a given methacryloxy or acryloxy containing compound and (ii) 2 to 20 parts per million of platinum on Y-alumina or charcoal; (c) combining the contents of the two reservoirs in a reactor vessel at 80°-120° centigrade; (d) post treating the crude reaction product with 1-3% alcohol by weight based on weight of product or post heating the reaction product for 20-30 minutes at 100°-140° C.; and (e) vacuum distilling the post treated product in the presence of phenolic or nonphenolic inhibitors or diphenylenediamine and under reduced pressure.
Claim 62
Dependent Claim
300 words
A process for preparing methacryloxy or acryloxy containing organosilicon compounds without undesirable polymerization which process comprises: (a) charging a first reservoir with (i) 3-5% molar excess of a methacryloxy or acryloxy functional containing compound ##STR19## wherein R" is hydrogen, a lower alkyl group having 2 to 8 carbons or an aryl group having 6 to 10 carbons, X is CH 2 CH 2 O or CH 2 or a combination of the two groups, 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) 0.5 to 2.0% monomethyl ether of hydroquinone, Isonox™ 129 or Ionol inhibitor by weight based on the amount of methacryloxy or acryloxy used; (b) charging a second reservoir with (i) a stochiometric amount of alkoxysilane ##STR20## wherein R and R' are lower alkyl moiety containing 1 to 4 carbons and n is 0 to 1 or a stochiometric amount of an Si--H containing silicone ##STR21## where x ranges from 0 to 100 and y ranges from 1 to 30 which alkoxysilane or Si--H containing silicone is needed to form a complete reaction with the methacryloxy or acryloxy containing compound employed in (a); and (ii) 2 to 100 parts per million of homogeneous soluble platinum complex selected from the group consisting of chloroplatinic acid, bis-(ethyleneplatinous)chloride, dichlorobis(acetonitrile)platinum (II), cis-dichlorobis(triphenylphosphine) platinum (II) and tetrakis(tetraphenyl phosphine)platinum (O); (c) combining the contents of the two reservoirs in a reactor vessel at 90°-120° centigrade; (d) post treating the crude reaction product with 1-3% alcohol by weight based on weight of product or post heating the reaction product for 20-30 minutes at 110°-130° C.; and (e) vacuum distilling the post-treated product in the presence of phenolic or nonphenolic inhibitors under reduced pressure.
Claim 63
Dependent Claim
300 words
A process for preparing methacryloxy or acryloxy containing organosilicon compounds without undesirable polymerization which process comprises: (a) charging a first reservoir with (i) 3-5% molar excess of a methacryloxy or acryloxy functional containing compound ##STR19## wherein R" is hydrogen, a lower alkyl group having 2 to 8 carbons or an aryl group having 6 to 10 carbons, X is CH 2 CH 2 O or CH 2 or a combination of the two groups, 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) 0.5 to 2.0% monomethyl ether of hydroquinone, Isonox™ 129 or Ionol inhibitor by weight based on the amount of methacryloxy or acryloxy used; (b) charging a second reservoir with (i) a stochiometric amount of alkoxysilane ##STR20## wherein R and R' are lower alkyl moiety containing 1 to 4 carbons and n is 0 to 1 or a stochiometric amount of an Si--H containing silicone ##STR21## where x ranges from 0 to 100 and y ranges from 1 to 30 which alkoxysilane or Si--H containing silicone is needed to form a complete reaction with the methacryloxy or acryloxy containing compound employed in (a); and (ii) 2 to 100 parts per million of homogeneous soluble platinum complex selected from the group consisting of chloroplatinic acid, bis-(ethyleneplatinous)chloride, dichlorobis(acetonitrile)platinum (II), cis-dichlorobis(triphenylphosphine) platinum (II) and tetrakis(tetraphenyl phosphine)platinum (O); (c) combining the contents of the two reservoirs in a reactor vessel at 90°-120° centigrade; (d) post treating the crude reaction product with 1-3% alcohol by weight based on weight of product or post heating the reaction product for 20-30 minutes at 110°-130° C.; and (e) vacuum distilling the post-treated product in the presence of phenolic or nonphenolic inhibitors under reduced pressure.
Claim 64
Dependent Claim
17 words
The process of claim 57 wherein the homogeneous soluble platinum complex is used as solution in solvents.
Claim 65
Dependent Claim
14 words
The process of claim 58 wherein the solvent is isopropanol, acetonitrile or 1,2 dimexhoxyethane.
Claim 66
Dependent Claim
264 words
A process for preparing, purifying and/or storing methacryloxy or acryloxy containing organosilicon compounds without undesirable polymerization which process comprises: (a) charging a first reservoir with (i) 3-5% molar excess of a methacryloxy or acryloxy functional containing compound ##STR22## wherein R" is hydrogen, a lower alkyl group having 2 to 8 carbons or an aryl group having 6 to 10 carbons, X is CH 2 CH 2 O or a CH 2 or a combination of the two groups, over a stochiometric amount of alkoxysilane or Si--H containing compound which would be needed to form a complete reaction between said functional containing compound and said organosilane or silicone; and (ii) 0.5 to 2.0% monomethyl ether of hydroquinone, Isonox™ 129, or Ionol inhibitor by weight based on the amount of methacryloxy or acryloxy used; and (iii) stabilizer; (b) charging a second reservoir with (i) a stochiometric amount of alkoxysilane ##STR23## wherein R and R' are lower alkyl moiety containing 1-4 carbons and n is 0 to 1 or a stochiometric amount of an Si--H containing silicone ##STR24## where x ranges from 0 to 100 and y ranges from 1 to 30 which alkoxysilane or Si--H containing silicone is needed to form a complete reaction with the methacryloxy or acryloxy containing compound employed in (a); and (ii) 20-100 parts per million of platinum on Y-alumina or charcoal; (c) combining the contents of the two reservoirs in a reactor vessel at 80-120° centigrade; and (d) vacuum distilling the product in the presence of phenolic or nonphenolic inhibitors monomethyl ether of hydroquinone, phenothiazine or diphenylenediamine and under reduced pressure.
Claim 67
Dependent Claim
264 words
A process for preparing, purifying and/or storing methacryloxy or acryloxy containing organosilicon compounds without undesirable polymerization which process comprises: (a) charging a first reservoir with (i) 3-5% molar excess of a methacryloxy or acryloxy functional containing compound ##STR22## wherein R" is hydrogen, a lower alkyl group having 2 to 8 carbons or an aryl group having 6 to 10 carbons, X is CH 2 CH 2 O or a CH 2 or a combination of the two groups, over a stochiometric amount of alkoxysilane or Si--H containing compound which would be needed to form a complete reaction between said functional containing compound and said organosilane or silicone; and (ii) 0.5 to 2.0% monomethyl ether of hydroquinone, Isonox™ 129, or Ionol inhibitor by weight based on the amount of methacryloxy or acryloxy used; and (iii) stabilizer; (b) charging a second reservoir with (i) a stochiometric amount of alkoxysilane ##STR23## wherein R and R' are lower alkyl moiety containing 1-4 carbons and n is 0 to 1 or a stochiometric amount of an Si--H containing silicone ##STR24## where x ranges from 0 to 100 and y ranges from 1 to 30 which alkoxysilane or Si--H containing silicone is needed to form a complete reaction with the methacryloxy or acryloxy containing compound employed in (a); and (ii) 20-100 parts per million of platinum on Y-alumina or charcoal; (c) combining the contents of the two reservoirs in a reactor vessel at 80-120° centigrade; and (d) vacuum distilling the product in the presence of phenolic or nonphenolic inhibitors monomethyl ether of hydroquinone, phenothiazine or diphenylenediamine and under reduced pressure.
Claim 68
Dependent Claim
18 words
The process of claim 60 wherein the stabilizers is selected from the group consisting of diketones and ketoesters.
Claim 69
Dependent Claim
14 words
The process of claim 61 wherein the diketone is pentadione- 2,4 or hexadione 2,5.
Claim 70
Dependent Claim
11 words
The process of claim 61 wherein the ketoester is methyl acetoacetate.
Claim 71
Dependent Claim
16 words
The process of claim 61 wherein the stabilizer is additionally mono keto or ester containing compound.
Claim 72
Dependent Claim
21 words
The process of claim 64 wherein the mono keto or ester containing compound is mesityl oxide, pentanone- 2 or methyl proprionate.
Claim 73
Dependent Claim
276 words
A process for preparing, purifying and/or storing methacryloxy or acryloxy containing organosilicon compounds without undesirable polymerization which process comprises: (a) charging a first reservoir with (i) 3-5% molar excess of a methacryloxy or acryloxy functional containing compound ##STR25## wherein R" is hydrogen, a lower alkyl group having 2 to 8 carbons or an aryl group having 6 to 10 carbons, X is CH 2 CH 2 O or a CH 2 or a combination of the two groups, 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; (ii) 0.5 to 2.0% monomethyl ether of hydroquinone, Isonox™ 129 or Ionol inhibitor by weight based on the amount of methacryloxy or acryloxy used; and (b) charging a second reservoir with (i) a stochiometric amount of alkoxysilane ##STR26## wherein R and R' are lower alkyl moiety 30 containing 1 to 4 carbons and n is 0 to 1 or a stochiometric amount of Si--H containing silicone ##STR27## where x ranges from 0 to 100 and y ranges from 1 to 30 which alkoxysilane or Si--H containing silicone is needed to form a complete reaction with the methacryloxy or acryloxy containing compound employed in (a); and (ii) 2 to 100 parts per million of homogeneous soluble platinum complex selected from the group consisting of chloroplatinic acid, bis-(ethyleneplatinous)chloride, dichlorobis(acetonitrile)platinum (II), cis-dichlorobis(triphenylphosphine) platinum (II) and tetrakis(tetraphenyl phosphine) platinum (O); (c) combining the contents of the two reservoirs in a reactor vessel at 90°-120° centigrade; and (d) vacuum distilling the product in the presence of phenolic and nonphenolic inhibitors and under reduced pressure.
Claim 74
Dependent Claim
276 words
A process for preparing, purifying and/or storing methacryloxy or acryloxy containing organosilicon compounds without undesirable polymerization which process comprises: (a) charging a first reservoir with (i) 3-5% molar excess of a methacryloxy or acryloxy functional containing compound ##STR25## wherein R" is hydrogen, a lower alkyl group having 2 to 8 carbons or an aryl group having 6 to 10 carbons, X is CH 2 CH 2 O or a CH 2 or a combination of the two groups, 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; (ii) 0.5 to 2.0% monomethyl ether of hydroquinone, Isonox™ 129 or Ionol inhibitor by weight based on the amount of methacryloxy or acryloxy used; and (b) charging a second reservoir with (i) a stochiometric amount of alkoxysilane ##STR26## wherein R and R' are lower alkyl moiety 30 containing 1 to 4 carbons and n is 0 to 1 or a stochiometric amount of Si--H containing silicone ##STR27## where x ranges from 0 to 100 and y ranges from 1 to 30 which alkoxysilane or Si--H containing silicone is needed to form a complete reaction with the methacryloxy or acryloxy containing compound employed in (a); and (ii) 2 to 100 parts per million of homogeneous soluble platinum complex selected from the group consisting of chloroplatinic acid, bis-(ethyleneplatinous)chloride, dichlorobis(acetonitrile)platinum (II), cis-dichlorobis(triphenylphosphine) platinum (II) and tetrakis(tetraphenyl phosphine) platinum (O); (c) combining the contents of the two reservoirs in a reactor vessel at 90°-120° centigrade; and (d) vacuum distilling the product in the presence of phenolic and nonphenolic inhibitors and under reduced pressure.
Claim 75
Dependent Claim
18 words
The process of claim 66 wherein the stabilizer is selected from the group consisting of diketones and ketoesters.
Claim 76
Dependent Claim
14 words
The process of claim 67 wherein the diketone is pentadione- 2,4 or hexadione- 2,5.
Claim 77
Dependent Claim
11 words
The process of claim 67 wherein the ketoester ss methyl acetoacetate.
Claim 78
Dependent Claim
17 words
The process of claim 67 wherein the stabilizer is additionally a mono keto or ester containing compound.
Claim 79
Dependent Claim
21 words
The process of claim 70 wherein the mono keto or ester containing compound is mesityl oxide, pentanone- 2 or methyl proprionate.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1990-11-23 | 1991-05-25 | 1991-11-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-11-23 | 1995-05-25 | 1995-11-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-11-23 | 1999-05-25 | 1999-11-24 | $7700.00 | Window Closed / Lapsed |