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Addition-curable silicone adhesive compositions, and bis(trialkoxysilylalkyleneoxy-carbonylalkylene) amine adhesion promoters

Assignee: General Electric Co
•
Filing: 1993-12-15
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Granted: 1994-08-30
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Expires: 2013-12-15
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Abstract

Abstract Addition-curable platinum group metal catalyzed silicone compositions are provided which utilize a bis(trialkoxysilylalkyleneoxycarbonylalkylene)amine adhesion promoter, such as NH[CH2CH2C(O)OCH2CH2CH2Si(OCH3)3]2. Cohesive bonding is effected on both plastic and metal substrates at temperatures of 100 DEG C. or less and in 1 hour or less.

Inventors

  • 👤 Judith Stein
  • 👤 Joseph A. King, Jr.
  • 👤 Andrew J. Caruso

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-28 21:05
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/54; C08K5/544; C07; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/18; C07F7/1804; C08K3/00; C08K3/34; C08K3/36; C08L; C08L83/00; C08L83/04; C08G; C08G77/00; C08G77/04; C08G77/12; C08G77/20; C08G77/22; C08G77/24; C08G77/42; C08G77/44; C08G77/70

Claims Analysis

Total Claims: 10
Claim 1
Independent Claim 364 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]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(trialkoxysilylalkyleneoxycarbonylalkylene)amine having the formula, NH[R.sup.3 C(O)OR.sup.4 Si(OR.sup.5).sub.3]2, which is effective as an adhesion promoter, where R 3 and R 4 are selected from the same or different C.sub.(2-8) alkylene radicals,and R 5 is selected from the same or different C.sub.(1-4) alkyl radicals, (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 364 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]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(trialkoxysilylalkyleneoxycarbonylalkylene)amine having the formula, NH[R.sup.3 C(O)OR.sup.4 Si(OR.sup.5).sub.3]2, which is effective as an adhesion promoter, where R 3 and R 4 are selected from the same or different C.sub.(2-8) alkylene radicals,and R 5 is selected from the same or different C.sub.(1-4) alkyl radicals, (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 17 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 28 words
An addition-curable composition in accordance with claim 1, where the adhesion promoter is NH[CH 2 CH 2 C(O)OCH 2 CH 2 CH 2 Si(OCH 3 ) 3]2 .
Claim 7
Dependent Claim 37 words
A bis(trialkoxysilylalkyleneoxycarbonylalkylene)amine having the formula, NH[R.sup.3 C(O)OR.sup.4 Si(OR.sup.5).sub.3]2 where R 3 and R 4 are selected from the same or different C.sub.(2-8) alkylene radicals, and R 5 is selected from the same or different C.sub.(1-4) alkyl radicals.
Claim 8
Dependent Claim 37 words
A bis(trialkoxysilylalkyleneoxycarbonylalkylene)amine having the formula, NH[R.sup.3 C(O)OR.sup.4 Si(OR.sup.5).sub.3]2 where R 3 and R 4 are selected from the same or different C.sub.(2-8) alkylene radicals, and R 5 is selected from the same or different C.sub.(1-4) alkyl radicals.
Claim 9
Dependent Claim 17 words
The compound, NH[CH 2 CH 2 C(O)OCH 2 CH 2 CH 2 Si(OCH 3 ) 3]2 .
Claim 10
Dependent Claim 17 words
The compound, NH[CH 2 CH 2 C(O)OCH 2 CH 2 CH 2 Si(OCH 3 ) 3]2 .

References Cited (Backward Citations)

US4087585A Cited
US4332844A Cited
GB2116575A Cited
US4753978A 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) 1997-08-29 1998-02-28 1998-08-30 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 2001-08-29 2002-02-28 2002-08-30 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2005-08-29 2006-02-28 2006-08-30 $7700.00 Window Closed / Lapsed

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