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US 5,399,651 AGranted
Adhesion promoting additives and low temperature curing organosiloxane compositions containing same
AssigneeDow Corning Corporation
InventorsTheresa E. Gentle, Michael A. Lutz
Life of this patent
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Abstract
Adhesion additives for curable organosiloxane compositions comprise (I) a silane containing at least one alkoxy or enoloxy group, the remaining valences of the silicon atom being satisfied by groups bonded to silicon through oxygen and containing at least one H.sub.2 C.dbd.CR-- radical, where R is hydrogen or monovalent hydrocarbon, and (II) at least one organosilicon compound comprising (a) at least one group capable of participating in a hydrosilation reaction, and (b) at least one silicon-bonded alkoxy, enoloxy or silanol group.
Claims13
A curable organosiloxane composition comprising
- (A) a curable polyorganosiloxane;
- (B) an amount sufficient to cure said composition of a curing agent;
- (C) an amount sufficient to promote curing of said composition of a curing catalyst;
- and
- (D) an adhesion promoting additive in an amount sufficient to develop adhesion between said composition and a substrate in contact with said composition during curing thereof at temperatures below 100.degree. C., said additive comprising (I) a first liquid organosilicon compound of a formula selected from the group consisting of (R.sup.1 O).sub.a Si(OR.sup.2).sub.4-a and R.sup.3 [OSi(OR.sup.2).sub.3 ].sub.2, and (II) a second liquid organosilicon compound selected from the group consisting of
- (1):
- organosilanes wherein the silicon atom is bonded to (a) at least one alkoxy, enoloxy or silanol group and (b) at least one silicon-bonded hydrogen atom or ethylenically unsaturated group bonded to silicon through carbon that will participate in a hydrosilation reaction;
- and
- (2) organosiloxanes comprising (a) units of the formula R.sup.11.sub.d R.sup.12.sub.e SiO.sub.(4-d-e)/2, and (b) units containing at least one silicon-bonded alkoxy, enoloxy or silanol group,
- wherein
- said alkoxy groups contain from 1 to 4 carbon atoms;
- said enoloxy groups contain from 3 to 8 carbon atoms;
- R.sup.1 represents a radical selected from the group consisting of
- CH.sub.2 .dbd.C(R.sup.4)CH.sub.2 R.sup.8 --;
- CH.sub.2 .dbd.C(R.sup.4)R.sup.5 OR.sup.6 --;
- [CH.sub.2 .dbd.C(R.sup.4)R.sup.5 O].sub.b R.sup.9 --;
- [CH.sub.2 .dbd.C(R.sup.4)].sub.b R.sup.9 --;
- CH.sub.2 .dbd.C(R.sup.4)R.sup.8 C(O)OR.sup.6 --;
- CH.sub.2 .dbd.C(R.sup.4)R.sup.8 OC(O)OR.sup.6 -- and
- CH.sub.2 .dbd.C(R.sup.4)R.sup.5 OC(O)R.sup.7 --;
- each R.sup.2 is individually selected from the group consisting of alkyl radicals containing from 1 to 4 carbon atoms, 1-alkenyl and 1-cycloalkenyl radicals;
- R.sup.3 represents a divalent radical selected from the group consisting of
- CH.sub.2 .dbd.C(R.sup.4)R.sup.10 .dbd.;
- CH.sub.2 .dbd.C(R.sup.4)R.sup.5 OR.sup.10 .dbd.;
- CH.sub.2 .dbd.C(R.sup.4)R.sup.8 C(O)OR.sup.10 .dbd.;
- CH.sub.2 .dbd.C(R.sup.4)R.sup.8 OC(O)OR.sup.10 .dbd.;
- and
- CH.sub.2 .dbd.C(R.sup.4)R.sup.5 OC(O)R.sup.10 .dbd.;
- wherein
- R.sup.4 represents a hydrogen atom or an alkyl radical;
- R.sup.5 represents a hydrocarbylene or substituted hydrocarbylene radical;
- R.sup.6 is selected from the same group as R.sup.5, with the proviso that R.sup.6 contains at least two carbon atoms;
- R.sup.7 is selected from the same group as R.sup.5 ;
- R.sup.8 is selected from the group consisting of single bonds and R.sup.5 ;
- R.sup.9 is selected from the group consisting of unsubstituted and substituted hydrocarbon radicals with a valence of b+1;
- R.sup.10 is a trivalent hydrocarbon radical;
- R.sup.11 is selected from the group consisting of hydrogen and unsaturated groups bonded to silicon through carbon and capable of undergoing hydrosilation;
- R.sup.12 is selected from monovalent unsubstituted or substituted hydrocarbon radical;
- a is 1, 2 or 3;
- b is 2 or 3
- d is 0, 1, 2 or 3;
- and
- e is 0, 1 or 2;
- with the proviso that the sum of d and e does not exceed 3, and
- wherein said composition is cured using a reaction selected from the group consisting of hydrosilation reactions catalyzed by platinum group metals and compounds thereof;
- reactions of silicon-bonded hydrogen atoms with silanol groups;
- and, free radical reactions initiated by the decomposition of a photolyrically unstable compound.
44 more elements
A composition according to claim ;
- wherein said first liquid organosilicon compound is C11H.sub.21 OSi(OC.sub.2 H.sub.5).sub.3 and said second liquid organosilicon compound is the reaction product of an organohydrogensiloxane with less than a stoichiometric amount, based on the number of silicon-bonded hydrogen atoms in said organohydrogensiloxane, of a mixture of allylglycidyl ether and hexenyltrimethoxysilane.
An adhesion promoting composition for use with curable organosiloxane compositions, said adhesion promoting composition comprising:
- (I) a first liquid organosilicon compound of a formula selected. from the group consisting of (R.sup.1 O).sub.a Si(OR.sup.2).sub.4-a and R.sup.3 [OSi(OR.sup.2).sub.3 ].sub.2, and
- (II) a second liquid organosilicon compound selected from the group consisting of
- (1) organosilanes wherein the silicon atom is bonded to (a) at least one alkoxy, enoloxy or silanol group and (b) at least one silicon-bonded hydrogen atom or ethylenically unsaturated group bonded to silicon through carbon that will participate in a hydrosilation reaction;
- and
- (2) organosiloxanes comprising (a) units of the formula R.sup.11.sub.d R.sup.12.sub.e SiO.sub.(4-d-e)/2, and (b) units containing at least one silicon-bonded alkoxy, enoloxy or silanol group,
- wherein said alkoxy groups contain from 1 to 4 carbon atoms;
- said enoloxy groups contain from 3 to 8 carbon atoms;
- R.sup.1 represents a radical selected from the group consisting of
- CH.sub.2 .dbd.C(R.sup.4)R.sup.5 OR.sup.6 --;
- [CH.sub.2 .dbd.C(R.sup.4)R.sup.5 O].sub.b R.sup.9 --;
- [CH.sub.2 .dbd.C(R.sup.4)].sub.b R.sup.9 --;
- [CH.sub.2 .dbd.C(R.sup.4)R.sup.8 C(O)OR.sup.6 --;
- CH.sub.2 .dbd.C(R.sup.4)R.sup.8 OC(O)OR.sup.6 -- and
- CH.sub.2 .dbd.C(R.sup.4)R.sup.5 OC(O)R.sup.7 --;
- each R.sup.2 is individually selected from the group consisting of alkyl radicals containing from 1 to 4 carbon atoms,
- 1-alkenyl and 1-cycloalkenyl radicals;
- R.sup.3 represents a divalent radical selected from the group consisting of
- CH.sub.2 .dbd.C(R.sup.4)R.sup.10 .dbd.;
- CH.sub.2 .dbd.C(R.sup.4)R.sup.5 OR.sup.10 .dbd.;
- CH.sub.2 .dbd.C(R.sup.4)R.sup.8 C(O)OR.sup.10 .dbd.;
- CH.sub.2 .dbd.C(R.sup.4)RSOC(O)OR.sup.10.dbd.;
- and
- CH.sub.2 .dbd.C(R.sup.4)R.sup.5 OC(O)R.sup.10 .dbd.;
- wherein R.sup.4 is selected from the hydrogen atom or an alkyl radical;
- R.sup.5 is selected from a hydrocarbylene or substituted hydrocarbylene radical;
- R.sup.6 is selected from the same group as R.sup.5, with the proviso that R.sup.6 contains at least two carbon atoms;
- R.sup.7 is selected from the same group as R.sup.5 ;
- R.sup.8 is selected from the group consisting of single bonds and R.sup.5 ;
- R.sup.9 is selected from the group consisting of unsubstituted and substituted hydrocarbon radical with a valence of b+1;
- R.sup.10 is a trivalent hydrocarbon radical;
- R.sup.11 is selected from the group consisting of hydrogen and unsaturated groups bonded to silicon through carbon and capable of undergoing hydrosilation;
- R.sup.12 is selected from the group consisting of monovalent unsubstituted and substituted hydrocarbon radicals;
- a is 1, 2 or 3;
- b is 2 or 3
- d is 1, 2 or 3;
- and
- e is 0, 1 or 2;
- with the proviso that the sum of d and e does not exceed 3.
35 more elements
Dependencies are inferred from the claim text.