Blocked mercaptosilane coupling agents for filled rubbers
View Patent ↗A blocked mercaptosilane of the structure: G-C(═O)—S—CH 2 CH 2 CH 2 SiX 3 is disclosed wherein each X is an independently selected RO— group or R— group wherein each R is independently selected from the group consisting of hydrogen, alkyl that may or may not contain unsaturation, alkenyl groups, aryl groups, and aralkyl groups, such moieties other than hydrogen having from 1 to 18 carbon atoms, at least one X is RO—, and G is a monovalent alkyl group.
1. A blocked mercaptosilane of the structure:
G-C(═O)—S—CH 2 CH 2 CH 2 SiX 3
wherein
each X is an independently selected RO— or R— group wherein each R is independently selected from the group consisting of hydrogen, alkyl that may or may not contain unsaturation, alkenyl groups, aryl groups, and aralkyl groups, such moieties other than hydrogen having from 1 to 18 carbon atoms, at least one X is RO—, and
G is a monovalent alkyl of from 9 to 18 carbon atoms.
2. The blocked mercaptosilane of claim 1 wherein G is a monovalent alkyl of from 9 to 14 carbon atoms.
3. The blocked mercaptosilane of claim 1 wherein R is selected from the group consisting of methyl, ethyl, propyl, isobutyl, phenyl, tolyl, phenethyl, norbornyl, norbornenyl, ethylnorbornyl, ethylnorbornenyl, ethylcyclohexyl, ethylcyclohexenyl, and cyclohexylcyclohexyl.
4. The blocked mercaptosilane of claim 3 wherein R is methyl or ethyl.
5. The blocked mercaptosilane of claim 3 wherein each X in SiX 3 is selected from the group consisting of methyl and ethoxy.
6. A composition comprising a filler in combination with a blocked mercaptosilane of the structure:
G-C(═O)—S—CH 2 CH 2 CH 2 SiX 3
wherein
each X is an independently selected RO— or R— group wherein each R is independently selected from the group consisting of hydrogen, alkyl that may or may not contain unsaturation, alkenyl groups, aryl groups, and aralkyl groups, such moieties other than hydrogen having from 1 to 18 carbon atoms, at least one X is RO—, and
G is a monovalent alkyl of from 9 to 18 carbon atoms.
7. The composition of claim 6 wherein G is a monovalent alkyl of from 9 to 14 carbon atoms.
8. The composition of claim 6 wherein R is selected from the group consisting of methyl, ethyl, propyl, isobutyl, phenyl, tolyl, phenethyl, norbornyl, norbornenyl, ethylnorbornyl, ethylnorbornenyl, ethylcyclohexyl, ethylcyclohexenyl, and cyclohexylcyclohexyl.
9. The composition of claim 8 wherein R is methyl or ethyl.
10. The composition of claim 8 wherein each X in SiX 3 is selected from the group consisting of methyl and ethoxy.
11. The composition of claim 6 wherein the filler is silica.
12. A composition comprising an organic polymer in combination with a blocked mercaptosilane of the structure:
G-C(═O)—S—CH 2 CH 2 CH 2 SiX 3
wherein
each X is an independently selected RO— or R— group wherein each R is independently selected from the group consisting of hydrogen, alkyl that may or may not contain unsaturation, alkenyl groups, aryl groups, and aralkyl groups, such moieties other than hydrogen having from 1 to 18 carbon atoms, at least one X is RO—, and
G is a monovalent alkyl of from 9 to 18 carbon atoms.
13. The composition of claim 12 wherein G is a monovalent alkyl of from 9 to 14 carbon atoms.
14. The composition of claim 12 wherein the organic polymer is selected from the group consisting of solution styrene-butadiene rubber, styrene-butadiene rubber, natural rubber, polybutadiene, ethylene-propylene co- and ter-polymers, and acrylonitrile-butadiene rubber.
15. A rubber composition comprising:
a) a blocked mercaptosilane of the structure:
G-C(═O)—S—CH 2 CH 2 CH 2 SiX 3
wherein
each X is an independently selected RO— or R— group wherein each R is independently selected from the group consisting of hydrogen, alkyl that may or may not contain unsaturation, alkenyl groups, aryl groups, and aralkyl groups, such moieties other than hydrogen having from 1 to 18 carbon atoms, at least one X is RO—, and
G is a monovalent alkyl of from 9 to 18 carbon atoms;
b) an organic polymer; and
c) a filler.
16. The rubber composition of claim 15 wherein R is selected from the group consisting of methyl, ethyl, propyl, isobutyl, phenyl, tolyl, phenethyl, norbornyl, norbornenyl, ethylnorbornyl, ethylnorbornenyl, ethylcyclohexyl, ethylcyclohexenyl, and cyclohexylcyclohexyl.
17. The rubber composition of claim 16 wherein R is methyl or ethyl.
18. The rubber composition of claim 16 wherein each X in SiX 3 is selected from the group consisting of methyl and ethoxy.
19. An article of manufacture comprising a rubber composition comprising:
a) a blocked mercaptosilane of the structure:
G-C(═O)—S—CH 2 CH 2 CH 2 SiX 3
wherein
each X is an independently selected RO— or R— group wherein each R is independently selected from the group consisting of hydrogen, alkyl that may or may not contain unsaturation, alkenyl groups, aryl groups, and aralkyl groups, such moieties other than hydrogen having from 1 to 18 carbon atoms, at least one X is RO—, and
G is a monovalent alkyl of from 9 to 18 carbon atoms;
b) an organic polymer; and
c) a filler.
20. The article of claim 19 wherein G is a monovalent alkyl of from 9 to 14 carbon atoms.
21. The article of claim 19 wherein said article is a tire.
22. The tire of claim 21 wherein R is selected from the group consisting of methyl, ethyl, propyl, isobutyl, phenyl, tolyl, phenethyl, norbornyl, norbornenyl, ethylnorbornyl, ethylnorbornenyl, ethylcyclohexyl, ethylcyclohexenyl, and cyclohexylcyclohexyl.
23. The tire of claim 22 wherein R is methyl or ethyl.
24. The tire of claim 22 wherein each X in SiX 3 is selected from the group consisting of methyl and ethoxy.
25. A composition consisting essentially of a carrier and a blocked mercaptosilane of the structure:
G-C(═O)—S—CH 2 CH 2 CH 2 SiX 3
wherein
each X is an independently selected RO— or R— group wherein each R is independently selected from the group consisting of hydrogen, alkyl that may or may not contain unsaturation, alkenyl groups, aryl groups, and aralkyl groups, such moieties other than hydrogen having from 1 to 18 carbon atoms, at least one X is RO—, and
G is a monovalent alkyl of from 9 to 18 carbon atoms.
26. The blocked mercaptosilane of claim 25 wherein G is a monovalent alkyl of from 9 to 14 carbon atoms.
27. The composition of claim 25 wherein the carrier is a filler.
28. The composition of claim 27 wherein the filler is selected from the group consisting of silica and carbon black.
29. The composition of claim 27 which is the reaction product of the filler and the blocked mercaptosilane.
30. The composition of claim 29 wherein the filler and blocked mercaptosilane are reacted through the SiX 3 group of the blocked mercaptosilane.
31. The composition of claim 25 wherein the carrier is a porous polymer.