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Addition-curable silicone adhesive compositions and N-heterocyclic silane adhesion promoters

Assignee: General Electric Co
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Filing: 1993-12-13
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Granted: 1994-11-08
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Expires: 2013-12-13
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Abstract

Abstract Addition-curable platinum group metal catalyzed silicone compositions are provided which utilize an N-heterocyclic adhesion promoter, such as bis(trimethoxysilyltrimethylene) 2,6 pyridine dicarboxylate. Cohesive bonding is effected on both plastic and metal substrates at temperatures of less than 100° C. and in less than 1 hour.

Inventors

  • 👤 Judith Stein

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-09 07:11
CPC Classifications
C; C08; C08L; C08L83/00; C08L83/04; C08K; C08K5/00; C08K5/54; C08K5/544; C08K5/5477; C09; C09J; C09J183/00; C09J183/04; C08L2666/00; C08L2666/28; C08L2666/44

Claims Analysis

Total Claims: 6
Claim 1
Independent Claim 359 words
An addition-curable composition, comprising by weight, (A) 100 parts of a vinyl-containing polydiorganosiloxane composition comprising: (1) about 50 to about 100 parts of an essentially cyclic-free vinyl-terminated polydiorganosiloxane having the general formula, (R).sub.2 V.sub.i SiO[(R).sub.2 SiO].sub.m [RV.sub.i SiO].sub.n S.sub.i (R).sub.2 V.sub.i, where Vi is a vinyl radical, R is selected from the class consisting of alkyl radicals having 1 to 8 carbon atoms, phenyl radicals, fluoroalkyl radicals having 3 to 10 carbon atoms and mixtures thereof, "m+n" has a value sufficient to provide a polydiorganosiloxane viscosity of 100 to about 100,000 centipoise at 25° C. and a polydiorganosiloxane vinyl content of from about 0.02 to about 2.0 weight %, and (2) from about 0 to about 50 parts of a solid, benzene-soluble vinyl-containing resin copolymer comprising, (R.sup.1).sub.3 SiO.sub.1/2 units and SiO.sub.4/2 units, where R 1 is a vinyl radical, or a monovalent hydrocarbon radical free of aliphatic unsaturation and containing no more than six carbon atoms, the ratio of (R 1 ) 3 SiO 1/2 units to SiO 4/2 units being from about 0.5:1 to about 1.5:1, and the resin having a vinyl content of from about 1.5 to about 3.5% by weight, (B) from about 1 to about 20 parts of a hydrogen-containing polysiloxane having an average unit formula, R.sup.2.sub.a H.sub.b SiO.sub.(4-a-b)/2, where R 2 is a monovalent hydrocarbon radical, or halogenated monovalent hydrocarbon radical having from 1 to about 10 carbon atoms and free of aliphatic unsaturation, "a" has a value of from about 0 to about 3, "b" has a value of from about 0 to about 3, and the sum of "a"+"b" has a value of from 0 to 3, (C) a catalytic amount of a hydrosilylation catalyst, (D) an amount of a bis[trialkyloxysilylalkenyl]pyridine dicarboxylate having the formula, [(R.sup.3 O).sub.3 S.sub.i R.sup.4 OOC].sub.2 C.sub.5 H.sub.3 N which is effective as an adhesion promoter, wherein R 3 is a C.sub.(1-4) alkyl radical and R 4 is a C.sub.(2-8) alkylene radical, (E) from about 0 to about 200 parts of an extending filler, and (F) from about 0 to about 50 parts of a reinforcing filler, and in the absence of (A)(2), an amount effective for reinforcement.
Claim 2
Dependent Claim 359 words
An addition-curable composition, comprising by weight, (A) 100 parts of a vinyl-containing polydiorganosiloxane composition comprising: (1) about 50 to about 100 parts of an essentially cyclic-free vinyl-terminated polydiorganosiloxane having the general formula, (R).sub.2 V.sub.i SiO[(R).sub.2 SiO].sub.m [RV.sub.i SiO].sub.n S.sub.i (R).sub.2 V.sub.i, where Vi is a vinyl radical, R is selected from the class consisting of alkyl radicals having 1 to 8 carbon atoms, phenyl radicals, fluoroalkyl radicals having 3 to 10 carbon atoms and mixtures thereof, "m+n" has a value sufficient to provide a polydiorganosiloxane viscosity of 100 to about 100,000 centipoise at 25° C. and a polydiorganosiloxane vinyl content of from about 0.02 to about 2.0 weight %, and (2) from about 0 to about 50 parts of a solid, benzene-soluble vinyl-containing resin copolymer comprising, (R.sup.1).sub.3 SiO.sub.1/2 units and SiO.sub.4/2 units, where R 1 is a vinyl radical, or a monovalent hydrocarbon radical free of aliphatic unsaturation and containing no more than six carbon atoms, the ratio of (R 1 ) 3 SiO 1/2 units to SiO 4/2 units being from about 0.5:1 to about 1.5:1, and the resin having a vinyl content of from about 1.5 to about 3.5% by weight, (B) from about 1 to about 20 parts of a hydrogen-containing polysiloxane having an average unit formula, R.sup.2.sub.a H.sub.b SiO.sub.(4-a-b)/2, where R 2 is a monovalent hydrocarbon radical, or halogenated monovalent hydrocarbon radical having from 1 to about 10 carbon atoms and free of aliphatic unsaturation, "a" has a value of from about 0 to about 3, "b" has a value of from about 0 to about 3, and the sum of "a"+"b" has a value of from 0 to 3, (C) a catalytic amount of a hydrosilylation catalyst, (D) an amount of a bis[trialkyloxysilylalkenyl]pyridine dicarboxylate having the formula, [(R.sup.3 O).sub.3 S.sub.i R.sup.4 OOC].sub.2 C.sub.5 H.sub.3 N which is effective as an adhesion promoter, wherein R 3 is a C.sub.(1-4) alkyl radical and R 4 is a C.sub.(2-8) alkylene radical, (E) from about 0 to about 200 parts of an extending filler, and (F) from about 0 to about 50 parts of a reinforcing filler, and in the absence of (A)(2), an amount effective for reinforcement.
Claim 3
Dependent Claim 16 words
An addition-curable composition in accordance with claim 1, where the vinyl-containing polydiorganopolysiloxane is a vinyl-containing polydimethylsiloxane.
Claim 4
Dependent Claim 37 words
An addition-curable composition in accordance with claim 1, where the solid, benzene-soluble vinyl-containing resin comprises a mixture of (CH 3 ) 3 SiO 1/2 units and Vi(CH 3 ) 2 SiO 1/2 units and SiO 2 units.
Claim 5
Dependent Claim 16 words
An addition-curable composition in accordance with claim 1, where the hydrosilylation catalyst is a platinum catalyst.
Claim 6
Dependent Claim 16 words
An addition-curable composition in accordance with claim 1, where the adhesion promoter is 2,6 bis(trimethoxysilyltrimethylene)pyridine dicarboxylate.

References Cited (Backward Citations)

US4087585A Cited
US4332844A Cited
US4980413A Cited
US5173529A Cited
US5164461A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1997-11-07 1998-05-09 1998-11-08 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 2001-11-07 2002-05-09 2002-11-08 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2005-11-07 2006-05-09 2006-11-08 $7700.00 Window Closed / Lapsed

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