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US5789485A Expired / Lapsed US ⏱️ 0.0 years remaining

Curable silicone compositions

Assignee: DuPont Toray Specialty Materials KK
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Filing: 1996-12-24
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Granted: 1998-08-04
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Expires: 2016-12-24
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Abstract

Abstract The present invention relates to a curable silicone composition comprising (A) an alkenyl-functional organopolysiloxane, (B) a siloxane-modified acrylic polymer, (C) an organohydrogenpolysiloxane, and (D) a hydrosilylation reaction catalyst. The curable silicone compositions of this invention cure into a highly oil-resistant and highly wear-resistant coating and are useful as base compositions for inks for silicone moldings, and are also useful for imparting release against pressure sensitive adhesives while maintaining a degree of printability.

Inventors

  • 👤 Akihiko Kobayashi
  • 👤 Takayoshi Otomo
  • 👤 Hiroaki Yoshida

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-09 16:24
CPC Classifications
C; C09; C09D; C09D183/00; C09D183/04; C09D183/10

Claims Analysis

Total Claims: 26
Claim 1
Independent Claim 194 words
A curable silicone composition comprising: (A) 100 weight parts of an organopolysiloxane having at least 2 silicon-bonded alkenyl groups per molecule and having a viscosity of 100 to 100,000 centistokes; (B) 1 to 150 weight parts of an acrylic polymer having the formula ##STR6## wherein R 1 is hydrogen or methyl, R 2 is a monovalent hydrocarbon group, R 3 is an alkylene group, R 4 is an alkyl group or an aryl group, R 5 is an alkenyl group, n is an integer having a value from 1 to 200, m is an integer having a value from 1 to 50, and p is an integer having a value from 1 to 200; (C) an organohydrogenpolysiloxane having at least 2 silicon-bonded hydrogen atoms per molecule in an amount sufficient to provide a ratio of 1:0.4 to 1:50 moles of alkenyl groups in component (A) to moles of silicon-bonded hydrogen atoms in Component (C) with the proviso that when component (A) is an organopolysiloxane having 2 silicon-bonded alkenyl groups per molecule then component (C) must have at least 3 silicon-bonded hydrogen groups per molecule; and (D) a catalytic quantity of a hydrosilylation reaction catalyst.
Claim 2
Dependent Claim 194 words
A curable silicone composition comprising: (A) 100 weight parts of an organopolysiloxane having at least 2 silicon-bonded alkenyl groups per molecule and having a viscosity of 100 to 100,000 centistokes; (B) 1 to 150 weight parts of an acrylic polymer having the formula ##STR6## wherein R 1 is hydrogen or methyl, R 2 is a monovalent hydrocarbon group, R 3 is an alkylene group, R 4 is an alkyl group or an aryl group, R 5 is an alkenyl group, n is an integer having a value from 1 to 200, m is an integer having a value from 1 to 50, and p is an integer having a value from 1 to 200; (C) an organohydrogenpolysiloxane having at least 2 silicon-bonded hydrogen atoms per molecule in an amount sufficient to provide a ratio of 1:0.4 to 1:50 moles of alkenyl groups in component (A) to moles of silicon-bonded hydrogen atoms in Component (C) with the proviso that when component (A) is an organopolysiloxane having 2 silicon-bonded alkenyl groups per molecule then component (C) must have at least 3 silicon-bonded hydrogen groups per molecule; and (D) a catalytic quantity of a hydrosilylation reaction catalyst.
Claim 3
Dependent Claim 45 words
A composition according to claim 1, wherein (A) is selected from the group consisting of dimethylvinylsiloxy-endblocked dimethylpolysiloxanes, dimethylvinylsiloxy-endblocked methylvinylpolysiloxanes, dimethylvinylsiloxy-endblocked methylphenylpolysiloxanes, dimethylvinylsiloxy-endblocked dimethylsiloxane-methylvinylsiloxane copolymers, dimethylvinylsiloxy-endblocked dimethylsiloxane-methylphenylsiloxane copolymers, dimethylvinylsiloxy-endblocked dimethylsiloxane-methylvinylsiloxane-methylphenylsiloxane copolymers, trimethylsiloxy-endblocked dimethylsiloxane-methylvinylsiloxane copolymers, trimethylsiloxy-endblocked dimethylsiloxane-methylvinylsiloxane-methylphenylsiloxane copolymers, dimethylhydroxysiloxy-endblocked methylvinylpolysiloxanes, dimethylhydroxysiloxy-endblocked dimethylsiloxane-methylvinylsiloxane copolymers, and dimethylhydroxysiloxy-endblocked dimethylsiloxane-methylvinylsiloxane-methylphenylsiloxane copolymers.
Claim 4
Dependent Claim 43 words
A composition according to claim 1, wherein R 1 , R 2 , and R 4 are methyl, R 3 is propylene, R 5 is vinyl, m is an integer from 1 to 20, and p is an integer from 1 to 10.
Claim 5
Dependent Claim 45 words
A composition according to claim 1, wherein (C) is selected from the group consisting of dimethylhydrogensiloxy-endblocked dimethylpolysiloxanes, dimethylhydrogensiloxy-endblocked methylhydrogenpolysiloxanes, dimethylhydrogensiloxy-endblocked methylphenylpolysiloxanes, dimethylhydrogensiloxy-endblocked dimethylsiloxane-methylhydrogensiloxane copolymers, dimethylhydrogensiloxy-endblocked dimethylsiloxane-methylphenylsiloxane copolymers, dimethylhydrogensiloxy-endblocked dimethylsiloxane-methylhydrogensiloxane-methylphenylsiloxane copolymers, trimethylsiloxy-endblocked dimethylsiloxane-methylhydrogensiloxane copolymers, trimethylsiloxy-endblocked dimethylsiloxane-methylhydrogensiloxane-methylphenylsiloxane copolymers, dimethylhydroxysiloxy-endblocked methylhydrogenpolysiloxanes, dimethylhydroxysiloxy-endblocked dimethylsiloxane-methylhydrogensiloxane copolymers, and dimethylhydroxysiloxy-endblocked dimethylsiloxane-methylhydrogensiloxane-methylphenylsiloxane copolymers.
Claim 6
Dependent Claim 50 words
A composition according to claim 1, wherein (D) is selected from the group consisting of chloroplatinic acid, alcohol-modified chloroplatinic acid, chloroplatinic acid-olefin complexes, divinyltetramethyldisiloxane complexes of platinum and chloroplatinic acid, platinum supported on alumina, platinum supported on silica, platinum supported on carbon black, platinum black, palladium catalysts, and rhodium catalysts.
Claim 7
Dependent Claim 31 words
A composition according to claim 1, wherein the composition further comprises at least one ingredient selected from the group consisting of silica, water, solvents, storage stabilizers, heat stabilizers, and flame retardents.
Claim 8
Dependent Claim 27 words
A composition according to claim 6, wherein the storage stabilizer is selected from the group consisting of acetylenic alcohols, unsaturated carboxylic esters, conjugated ene-ynes, and triallyl isocyanurate.
Claim 9
Dependent Claim 13 words
A composition according to claim 1, wherein the composition further comprises a pigment.
Claim 10
Dependent Claim 27 words
A composition according to claim 8, wherein the pigment is selected from the group consisting of microparticulate carbon black, microparticulate titanium oxide, and microparticulate iron oxide red.
Claim 11
Dependent Claim 200 words
A curable silicone composition obtained by a method comprising (I) mixing: (A) 100 weight parts of an organopolysiloxane having at least 2 silicon-bonded alkenyl groups per molecule and having a viscosity of 100 to 100,000 centistokes; (B) 1 to 150 weight parts of an acrylic polymer having the formula ##STR7## wherein R 1 is hydrogen or methyl, R 2 is a monovalent hydrocarbon group, R 3 is an alkylene group, R 4 is an alkyl group or an aryl group, R 5 is an alkenyl group, n is an integer having a value from 1 to 200, m is an integer having a value from 1 to 50, and p is an integer having a value from 1 to 200; (C) an organohydrogenpolysiloxane having at least 2 silicon-bonded hydrogen atoms per molecule in an amount sufficient to provide a ratio of 1:0.4 to 1:50 moles of alkenyl groups in component (A) to moles of silicon-bonded hydrogen atoms in Component (C) with the proviso that when component (A) is an organopolysiloxane having 2 silicon-bonded alkenyl groups per molecule then component (C) must have at least 3 silicon-bonded hydrogen groups per molecule; and (D) a catalytic quantity of a hydrosilylation reaction catalyst.
Claim 12
Dependent Claim 200 words
A curable silicone composition obtained by a method comprising (I) mixing: (A) 100 weight parts of an organopolysiloxane having at least 2 silicon-bonded alkenyl groups per molecule and having a viscosity of 100 to 100,000 centistokes; (B) 1 to 150 weight parts of an acrylic polymer having the formula ##STR7## wherein R 1 is hydrogen or methyl, R 2 is a monovalent hydrocarbon group, R 3 is an alkylene group, R 4 is an alkyl group or an aryl group, R 5 is an alkenyl group, n is an integer having a value from 1 to 200, m is an integer having a value from 1 to 50, and p is an integer having a value from 1 to 200; (C) an organohydrogenpolysiloxane having at least 2 silicon-bonded hydrogen atoms per molecule in an amount sufficient to provide a ratio of 1:0.4 to 1:50 moles of alkenyl groups in component (A) to moles of silicon-bonded hydrogen atoms in Component (C) with the proviso that when component (A) is an organopolysiloxane having 2 silicon-bonded alkenyl groups per molecule then component (C) must have at least 3 silicon-bonded hydrogen groups per molecule; and (D) a catalytic quantity of a hydrosilylation reaction catalyst.
Claim 13
Dependent Claim 45 words
A composition according to claim 10, wherein (A) is selected from the group consisting of dimethylvinylsiloxy-endblocked dimethylpolysiloxanes, dimethylvinylsiloxy-endblocked methylvinylpolysiloxanes, dimethylvinylsiloxy-endblocked methylphenylpolysiloxanes, dimethylvinylsiloxy-endblocked dimethylsiloxane-methylvinylsiloxane copolymers, dimethylvinylsiloxy-endblocked dimethylsiloxane-methylphenylsiloxane copolymers, dimethylvinylsiloxy-endblocked dimethylsiloxane-methylvinylsiloxane-methylphenylsiloxane copolymers, trimethylsiloxy-endblocked dimethylsiloxane-methylvinylsiloxane copolymers, trimethylsiloxy-endblocked dimethylsiloxane-methylvinylsiloxane-methylphenylsiloxane copolymers, dimethylhydroxysiloxy-endblocked methylvinylpolysiloxanes, dimethylhydroxysiloxy-endblocked dimethylsiloxane-methylvinylsiloxane copolymers, and dimethylhydroxysiloxy-endblocked dimethylsiloxane-methylvinylsiloxane-methylphenylsiloxane copolymers.
Claim 14
Dependent Claim 43 words
A composition according to claim 10, wherein R 1 , R 2 , and R 4 are methyl, R 3 is propylene, R 5 is vinyl, m is an integer from 1 to 20, and p is an integer from 1 to 10.
Claim 15
Dependent Claim 45 words
A composition according to claim 10, wherein (C) is selected from the group consisting of dimethylhydrogensiloxy-endblocked dimethylpolysiloxanes, dimethylhydrogensiloxy-endblocked methylhydrogenpolysiloxanes, dimethylhydrogensiloxy-endblocked methylphenylpolysiloxanes, dimethylhydrogensiloxy-endblocked dimethylsiloxane-methylhydrogensiloxane copolymers, dimethylhydrogensiloxy-endblocked dimethylsiloxane-methylphenylsiloxane copolymers, dimethylhydrogensiloxy-endblocked dimethylsiloxane-methylhydrogensiloxane-methylphenylsiloxane copolymers, trimethylsiloxy-endblocked dimethylsiloxane-methylhydrogensiloxane copolymers, trimethylsiloxy-endblocked dimethylsiloxane-methylhydrogensiloxane-methylphenylsiloxane copolymers, dimethylhydroxysiloxy-endblocked methylhydrogenpolysiloxanes, dimethylhydroxysiloxy-endblocked dimethylsiloxane-methylhydrogensiloxane copolymers, and dimethylhydroxysiloxy-endblocked dimethylsiloxane-methylhydrogensiloxane-methylphenylsiloxane copolymers.
Claim 16
Dependent Claim 50 words
A composition according to claim 10, wherein (D) is selected from the group consisting of chloroplatinic acid, alcohol-modified chloroplatinic acid, chloroplatinic acid-olefin complexes, divinyltetramethyldisiloxane complexes of platinum and chloroplatinic acid, platinum supported on alumina, platinum supported on silica, platinum supported on carbon black, platinum black, palladium catalysts, and rhodium catalysts.
Claim 17
Dependent Claim 35 words
A composition according to claim 10, wherein the method further comprises adding at least one ingredient selected from the group consisting of silica, water, solvents, storage stabilizers, heat stabilizers, and flame retardents during step (I).
Claim 18
Dependent Claim 27 words
A composition according to claim 15, wherein the storage stabilizer is selected from the group consisting of acetylenic alcohols, unsaturated carboxylic esters, conjugated ene-ynes, and triallyl isocyanurate.
Claim 19
Dependent Claim 17 words
A composition according to claim 10, wherein the method further comprises adding a pigment during step (I).
Claim 20
Dependent Claim 17 words
A composition according to claim 15, wherein the method further comprises adding a pigment during step (I).
Claim 21
Dependent Claim 27 words
A composition according to claim 17, wherein the pigment is selected from the group consisting of microparticulate carbon black, microparticulate titanium oxide, and microparticulate iron oxide red.
Claim 22
Dependent Claim 27 words
A composition according to claim 18, wherein the pigment is selected from the group consisting of microparticulate carbon black, microparticulate titanium oxide, and microparticulate iron oxide red.
Claim 23
Dependent Claim 218 words
A coated article obtained by a method comprising: (I) applying a curable silicone composition on the surface of a substrate wherein the curable silicone composition is obtained by mixing: (A) 100 weight parts of an organopolysiloxane having at least 2 silicon-bonded alkenyl groups per molecule and having a viscosity of 100 to 100,000 centistokes; (B) 1 to 150 weight parts of an acrylic polymer having the formula ##STR8## wherein R 1 is hydrogen or methyl, R 2 is a monovalent hydrocarbon group, R 3 is an alkylene group, R 4 is an alkyl group or an aryl group, R 5 is an alkenyl group, n is an integer having a value from 1 to 200, m is an integer having a value from 1 to 50, and p is an integer having a value from 1 to 200; (C) an organohydrogenpolysiloxane having at least 2 silicon-bonded hydrogen atoms per molecule in an amount sufficient to provide a ratio of 1:0.4 to 1:50 moles of alkenyl groups in component (A) to moles of silicon-bonded hydrogen atoms in Component (C) with the proviso that when component (A) is an organopolysiloxane having 2 silicon-bonded alkenyl groups per molecule then component (C) must have at least 3 silicon-bonded hydrogen groups per molecule; and (D) a catalytic quantity of a hydrosilylation reaction catalyst.
Claim 24
Dependent Claim 218 words
A coated article obtained by a method comprising: (I) applying a curable silicone composition on the surface of a substrate wherein the curable silicone composition is obtained by mixing: (A) 100 weight parts of an organopolysiloxane having at least 2 silicon-bonded alkenyl groups per molecule and having a viscosity of 100 to 100,000 centistokes; (B) 1 to 150 weight parts of an acrylic polymer having the formula ##STR8## wherein R 1 is hydrogen or methyl, R 2 is a monovalent hydrocarbon group, R 3 is an alkylene group, R 4 is an alkyl group or an aryl group, R 5 is an alkenyl group, n is an integer having a value from 1 to 200, m is an integer having a value from 1 to 50, and p is an integer having a value from 1 to 200; (C) an organohydrogenpolysiloxane having at least 2 silicon-bonded hydrogen atoms per molecule in an amount sufficient to provide a ratio of 1:0.4 to 1:50 moles of alkenyl groups in component (A) to moles of silicon-bonded hydrogen atoms in Component (C) with the proviso that when component (A) is an organopolysiloxane having 2 silicon-bonded alkenyl groups per molecule then component (C) must have at least 3 silicon-bonded hydrogen groups per molecule; and (D) a catalytic quantity of a hydrosilylation reaction catalyst.
Claim 25
Dependent Claim 29 words
A coated article according to claim 21, wherein the method further comprises (II) exposing the coating and the substrate to heat in an amount sufficient to cure the coating.
Claim 26
Dependent Claim 24 words
A coated article according to claim 22, wherein the method further comprises applying a pressure sensitive adhesive on the coated substrate after step (II).

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