Polyacrylate compositions
View Patent ↗The present invention provides curable poly(acrylate) compositions, cured reaction products of which demonstrate improved resistance to shrinkage when exposed to hydrocarbon fluids, such as transmission fluids and oil-and fuel-based fluids.
1. An uncured gasket composition curable in place on a first surface, comprising:
a (meth)acrylate component comprising a silyl-functionalized poly(acrylate); and
a diluent embraced by the following structure:
wherein Z is S, X and Y may be the same or different and may be hydroxy, alkyl, alkenyl, aryl, aralkyl, aralkenyl, alkoxy, alkenoxy and aryloxy and A is ═O, or alkoxy, alkenoxy or aryloxy.
2. The composition according to claim 1 , wherein the silyl-functionalized poly(acrylate) is
wherein R 1 is C 1 to C 6 alkyl, R 2 is C 1 to C 6 alkyl, a is integer from 0-3, q is an integer from 2 to about 1,000, and A is a hydrocarbon diradical containing at least one (meth)acrylate linkage.
3. The composition according to claim 1 , further comprising at least one of a phenylene diamine within structure I or a diphenyl amine within structure II, wherein structure I comprises:
wherein R and R 1 are each members individually selected from the group consisting of C 1-12 alkyl, C 2-12 alkenyl, C 3-12 cyclo or bicycloalkyl, C 6-18 aryl, and derivatives thereof, and x and y are each individually 0-2;
structure II comprises:
wherein R 2 and R 3 are each members individually selected from the group consisting of C 1-12 alkyl, C 2-12 alkenyl, C 3-12 cyclo or bicycloalkyl, C 6-18 aryl, and derivatives thereof, and n and m are each individually 0-5; and combinations thereof.
4. The composition according to claim 3 , wherein the phenylene diamine is represented by a member selected from the group consisting of:
(R is thus 1,3-dimethylbutyl and 4-dimethylpentyl);
5. The composition according to claim 3 , wherein the diphenyl amine is represented by a member selected from the group consisting of:
6. Reaction products of the composition according to claim 1 .
7. The composition according to claim 1 , further comprising at least one component which reduces shrinkage of the cured composition upon exposure of the cured composition to a hydrocarbon fluid, wherein the component is present in an amount sufficient to reduce shrinkage of the cured composition when exposed to a hydrocarbon fluid.
8. The composition of claim 7 , wherein the component is a polyolefin added to the composition in particulate form.
9. The composition of claim 8 , wherein the polyolefin is substantially dissolved in the composition.
10. The composition of claim 9 , wherein the polyolefin in particulate form is comprised of a polyolefin containing repeating units of at least one C 2 to C 7 alkene monomer.
11. The composition of claim 8 , wherein the component is present in an amount of about 1% to about 20% by weight of the composition.
12. The composition of claim 8 , wherein the component has an average particle size of about 0.1 to about 50 microns.
13. The composition of claim 1 , further comprising a moisture-cure catalyst.
14. The composition of claim 8 , wherein the component is polyethylene.
15. The composition of claim 1 , wherein A is ═O, or alkoxy, or alkenoxy.
16. An uncured composition for disposition and curing on a first sealing surface, comprising:
a) a curable silyl functionalized polyacrylate having the structure,
wherein each R 1 is independently selected from a C 1 to C 6 alkyl, each R 2 is independently selected from a C 1 to C 10 alkyl, a is integer from 0-3, q is an integer from 2 to about 1,000, A is a hydrocarbon diradical containing at least one (meth)acrylate linkage, and a cured product of the silyl functionalized polyacrylate shrinks upon exposure to hydrocarbon fluid;
b) a diluent embraced by the following structure:
wherein Z is S or P, X and Y may be the same or different and may be hydroxy, alkyl, alkenyl, aryl, aralkyl, aralkenyl, alkoxy, alkenoxy and aryloxy and A is ═O, or alkoxy, alkenoxy or aryloxy; and
c) a component capable of reducing shrinkage of the cured composition caused by exposure of the cured composition to a hydrocarbon fluid, wherein the component is present in an amount sufficient to reduce shrinkage of the cured composition when exposed to a hydrocarbon fluid.
17. The composition of claim 16 wherein Z is S and A is ═O, or alkoxy, or alkenoxy.