Diol-derived organofunctional silane and compositions containing same
View Patent ↗Described are diol-derived organofunctional silanes in which the silanes contain cyclic and bridged alkoxy groups derived from hydrocarbon-based diols and methods for the preparation of the silanes. Also described are rubber compositions containing the diol-derived organofunctional silanes, methods for the preparation of the rubber compositions and articles of manufacture containing the rubber compositions, in particular, automotive tires and components thereof.
1. A silane of the general formula:
wherein
each occurrence of G is independently a polyvalent group derived from an alkyl, alkenyl, aryl or aralkyl group, with G containing from 1 to 30 carbon atoms;
each occurrence of X is independently selected from the group consisting of R 1 O—, R 1 C(═O)O— and —R 1 , wherein each occurrence of R 1 is independently an alkyl group, an alkenyl group, an aryl group or and aralkyl group containing from 1 to 20 carbon atoms or a hydrogen;
each R 10 and R 11 is independently an alkyl group, an alkenyl group, an aryl group, or an aralkyl group containing 1 to 20 carbon atoms or a hydrogen;
each occurrence of Y is independently a monovalent organofunctional group selected from the group consisting of:
—O—CH 2 —C 2 H 3 O, —C 6 H 9 O, —CR 6 (—O—)CR 4 R 5 , —NR 4 C(═O)OR 5 , —OC(═O)NR 4 R 5 , —NR 4 C(═O)SR 5 , —SC(═O)NR 4 R 5 , —NR 4 C(═S)OR 5 , —OC(═S)NR 4 R 5 , —NR 4 C(═S)SR 5 , —SC(═S)NR 4 R 5 , maleimide, maleate, substituted maleate, fumurate, substituted fumurate, —CN, citraconimide, —OCN, —N═C═O, —SCN, —N═C═S, —SC(═S)OR 4 , —SC(═S)SR 4 , —SC(═O)SR 4 , —NR 4 C(═O)NR 5 R 6 , —NR 4 C(═S)NR 5 R 6 , R 4 C(═O)NR 5 —, —C(═O)NR 4 R 5 —, and R 4 C(═S)NR 4 —; —OH, —OR 4 , —SR 4 , —S—SR 4 , —S—S—SR 4 , —S—S—S—SR 4 , melamine and cyanurato wherein each occurrence of R 4 , R 5 and R 6 is independently an alkyl group, an alkenyl group, an aryl group, or an aralkyl group containing 1 to 20 carbon atoms or a hydrogen; and
each occurrence of the subscript f is independently an integer from 1 to 15.
2. The silane of claim 1 wherein each occurrence of Y is —O—CH 2 —C 2 H 3 O, —C 6 H 9 O, —NR 4 C(═O)NR 5 R 6 or —N═C═O group, wherein each R 4 , R 5 and R 6 is independently an alkyl group, an alkenyl group, an aryl group, or an aralkyl group containing from 1 to 20 carbon atoms or a hydrogen.
3. The silane of claim 1 wherein G is —(CH 2 ) m — wherein m is 1 to 12.
4. The silane of claim 1 wherein X is methoxy, ethoxy, propoxy, isopropoxy or isobutoxy.
5. The silane of claim 1 wherein X is R 1 —.
6. The silane of claim 5 wherein —R 1 is methyl, ethyl or propyl.
7. The silane of claim 1 wherein —O(R 10 CR 11 ) f O— is independently selected from divalent alkoxy groups derived from 1,3-propanediol, 2-methyl-1,3-propanediol, 1,3-butanediol and 2-methyl-2,4-pentanediol.
8. A sizing for fiberglass comprising the silane of claim 1 .
9. A sizing for fiberglass comprising the silane of claim 4 .
10. A sizing for fiberglass comprising the silane of claim 5 .
11. A sizing for fiberglass comprising the silane of claim 6 .
12. A sizing for fiberglass comprising the silane of claim 7 .
13. A rubber composition comprising
(a) at least one sulfur vulcanizable rubber selected from the group consisting of a conjugated diene homopolymer and a copolymer, a copolymer of at least one conjugated diene and aromatic vinyl compound, and mixtures thereof;
(b) at least one particulate filler;
(c) at least one silane of claim 1 ; and, optionally,
(d) at least one curing agent.
14. A rubber composition comprising
(a) at least one sulfur vulcanizable rubber selected from the group consisting of a conjugated diene homopolymer and a copolymer, a copolymer of at least one conjugated diene and aromatic vinyl compound, and mixtures thereof;
(b) at least one particulate filler;
(c) least one silane of claim 5 ; and, optionally,
(d) at least one curing agent.
15. A rubber composition comprising
(a) at least one sulfur vulcanizable rubber selected from the group consisting of a conjugated diene homopolymer and a copolymer, a copolymer of at least one conjugated diene and aromatic vinyl compound, and mixtures thereof;
(b) at least one particulate filler;
(c) least one silane of claim 6 ; and, optionally,
(d) at least one curing agent.
16. A rubber composition comprising
(a) at least one sulfur vulcanizable rubber selected from the group consisting of a conjugated diene homopolymer and a copolymer, a copolymer of at least one conjugated diene and aromatic vinyl compound, and mixtures thereof;
(b) at least one particulate filler;
(c) least one silane of claim 6 ; and, optionally,
(d) least one curing agent.
17. A rubber composition comprising
(a) at least one sulfur vulcanizable rubber selected from the group consisting of a conjugated diene homopolymer and a copolymer, a copolymer of at least one conjugated diene and aromatic vinyl compound, and mixtures thereof;
(b) at least one particulate filler;
(c) least one silane of claim 7 ; and, optionally,
(d) least one curing agent.
18. The cured rubber composition of claim 3 .
19. The cured rubber composition of claim 5 .
20. The cured rubber composition of claim 7 .