Rubber compositions
View Patent ↗A rubber composition is disclosed wherein the rubber composition contains at least an effective amount of at least one substituted or unsubstituted diaryl amine-containing compound having at least one substituted or unsubstituted, saturated or partially saturated C 5 -C 30 ring structure optionally containing one or more heteroatoms fused to at least one of the aryl rings.
1. A tire having at least one component with a visually observable outer surface, the at least one component comprising a first rubber composition comprising (a) one or more of a first rubber component; and (b) an effective amount of one or more of a first diaryl amine-containing compound represented by the general formula:
wherein n is from 0 to 3; m is from 0 to 3; each R and R 3 substituent is independently hydrogen, a straight or branched C 1 -C 32 alkyl group or alkenyl group, substituted or unsubstituted C 3 -C 12 group, substituted or unsubstituted C 5 -C 12 aryl group, hydroxyl-containing group, halogen group, substituted or unsubstituted C 1 -C 20 alkoxy group, ester-containing group, ether-containing group, polyether-containing group, amide-containing group, or amine-containing group or two R substituents and/or two R 3 substituents together with the carbon atom to which they are bonded are joined together to form a substituted or unsubstituted, saturated, partially saturated or unsaturated C 5 -C 30 ring structure optionally containing one or more heteroatoms;
R 1 and R 2 together with the carbon atom to which they are bonded are joined together to form a substituted or unsubstituted ring, and
R 4 and R 5 together with the carbon atom to which they are bonded are pined together to form a substituted or unsubstituted C 5 -C 30 cycloalkyl or cycloalkenyl ring.
2. The tire of claim 1 , wherein the first rubber component is selected from the group consisting of a natural rubber, homopolymer of a conjugated diolefin, copolymer of a conjugated diolefin and an ethylenically unsaturated monomer and mixtures thereof.
3. The tire of claim 1 , wherein the first rubber component is selected from the group consisting of a natural rubber, polyisoprene, polybutadiene, polystyrene-butadiene), styrene-isoprene copolymer, isoprene-butadiene copolymer, styrene-isoprene-butadiene terpolymer, polychloroprene, chloro-isobutene-isoprene, nitrile-chloroprene, styrene-chloroprene, poly (acrylonitrile-butadiene), ethylene-propylene-diene terpolymer and mixtures thereof.
4. The tire of claim 1 , where in the first diaryl amine-containing compound, R 1 and R 2 together with the carbon atom to which they are bonded are joined together to form a substituted or unsubstituted, 5 , 6- or 7-membered cycloalkyl or cycloalkenyl ring.
5. The tire of claim 4 , where in the first diaryl amine-containing compound, R and R 3 are hydrogen.
6. The tire of claim 1 , where in the first diaryl amine-containing compound, R 1 and R 2 together with the carbon atom to which they are bonded are joined together to form a substituted or unsubstituted 5 , 6- or 7-membered cycloalkyl or cycloalkenyl ring and R 4 and R 5 together with the carbon atom to which they are bonded are joined together to form a substituted or unsubstituted 5-, 6- or 7-membered cycloalkyl or cycloalkenyl ring.
7. The tire of claim 6 , wherein the first rubber component is a natural rubber.
8. The tire of claim 1 , wherein the first diaryl amine-containing compound of component (b) is present in the rubber composition in an amount of about 0.5 to about 8.0 parts per hundred parts by weight of rubber (phr).
9. The tire of claim 1 , wherein the first rubber composition further comprises at least one reinforcing filler.
10. The tire of claim 9 , wherein the reinforcing filler is carbon black, silica or both.
11. The tire of claim 10 , wherein the reinforcing filler is silica and the rubber composition further comprises at least one coupling agent.
12. The tire of claim 1 , wherein the first rubber composition further comprises one or more of a first antidegradant.
13. The tire of claim 1 , wherein the first rubber composition further comprises at least one compound selected from the group consisting of a phenol, hindered phenol, alkylated diphenylamine, 1,2-dihydro-2,2,4-trimethylquinoline, alkylated hydroquinone, N,N′-bis(alkyl)-para-phenylenediamine, N,N′-bis(aryl)-para-phenylenediamine, N-(alkyl)-N′-(aryl)-para-phenylenediamine, quinonediimine, thioester, phosphite, imidazole, naphthylamine, alkylated naphthylamine, triazine and combinations thereof.
14. The tire of claim 1 , wherein the at least one component is selected from at least a portion of a tire tread, tire sidewall or tire chafer or combination thereof.
15. The tire of claim 1 , wherein the at least one component is at least a portion of a tire sidewall to the exclusion of a tire tread.
16. The tire of claim 7 , wherein the at least one component is at least a portion of a tire sidewall to the exclusion of a tire tread.
17. The tire of claim 13 , wherein the at least one component is at least a portion of a tire sidewall to the exclusion of a tire tread.
18. The tire of claim 1 , further comprising a carcass, the carcass comprising a second rubber composition comprising (a) one or more of a second rubber component; and (b) an effective amount of one or more of a second substituted or unsubstituted diaryl amine-containing compound represented by the general formula:
wherein n is from 0 to 3; m is from 0 to 3; each R and R 3 substituent is independently hydrogen, a straight branched C 1 -C 32 alkyl group or alkenyl group, substituted or unsubstituted C 3 -C 12 cycloalkyl group, substituted or unsubstituted C 5 -C 12 aryl group, hydroxyl-containing group, halogen group, substituted or unsubstituted C 1 -C 20 alkoxy group, ester-containing group, ether-containing group, polyether-containing group, amide-containing group, or amine-containing group or two R substituents and/or two R 3 substituents together with the carbon atom to which they are bonded are joined together to form a substituted or unsubstituted, saturated, partially saturated or unsaturated C 5 -C 30 ring structure optionally containing one or more heteroatoms;
R 1 and R 2 together with the carbon atom to which they are bonded are joined together to form a substituted or unsubstituted C 5 -C 30 cycloalkyl or cycloalkenyl ring, and
R 4 and R 5 together with the carbon atom to which they are bonded are joined together to form a substituted or unsubstituted C 5 -C 30 cycloalkyl or cycloalkenyl ring.
19. The tire of claim 18 , wherein the second rubber component is a natural rubber.
20. The tire of claim 18 , wherein the second rubber composition further comprises one or more of a second antidegradant.
21. The tire of claim 18 , wherein the second rubber composition further comprises at least one compound selected from the group consisting of a phenol, hindered phenol, alkylated diphenylamine, 1,2-dihydro-2,2,4-trimethylquinoline, alkylated hydroquinone, N,N′-bis(alkyl)-para-phenylenediamine, N,N′-bis(aryl)-para-phenylenediamine, N-(alkyl)-N′-(aryl)-para-phenylenediamine, quinonediimine, thioester, phosphite, imidazole, naphthylamine, alkylated naphthylamine, triazine and combinations thereof.
22. A tire having a carcass, the carcass comprising a rubber composition comprising (a) at least one rubber component; and (b) an effective amount of at least one substituted or unsubstituted diaryl amine-containing compound represented by the general formula:
wherein n is from 0 to 3; m is from 0 to 3; each R and R 3 substituent is independently hydrogen, a straight or branched C 5 -C 32 alkyl group or alkenyl group, substituted or unsubstituted C 3 -C 12 cycloalkyl group, substituted or unsubstituted C 5 -C 12 aryl group, hydroxyl-containing group, halogen group, substituted or unsubstituted C 1 -C 20 alkoxy group, ester-containing group, ether-containing group, polyether-containing group, amide-containing group, or amine-containing group or two R substituents and/or two R 3 substituents together with the carbon atom to which they are bonded are joined together to form a substituted or unsubstituted saturated partially saturated or unsaturated C 5 -C 30 ring structure optionally containing one or more heteroatoms;
R 1 and R 2 together with the carbon atom to which they are bonded are joined together to form a substituted or unsubstituted C 5 -C 30 cycloalkyl or cycloalkenyl ring, and
R 4 and R 5 together with the carbon atom to which they are bonded are joined together to form a substituted or unsubstituted C 5 -C 30 cycloalkyl or cycloalkenyl ring.
23. The tire of claim 22 , wherein the rubber component is selected from the group consisting of a natural rubber, homopolymer of a conjugated diolefin, copolymer of a conjugated diolefin and an ethylenically unsaturated monomer and mixtures thereof.
24. The tire of claim 22 , where in the diaryl amine-containing compound, R 1 and R 2 together with the carbon atom to which they are bonded are joined together to form a substituted or unsubstituted 5-, 6- or 7-membered cylcoalkyl or cycloalkenyl ring.
25. The tire of claim 24 , where in the diaryl amine-containing compound, R, and R 3 are hydrogen.
26. The tire of claim 22 , where in the diaryl amine-containing compound, R 1 and R 2 together with the carbon atom to which they are bonded are joined together to form a substituted or unsubstituted 5-, 6- or 7-membered cycloalkyl or cycloalkenyl ring and R 4 and R 5 together with the carbon atom to which they are bonded are joined together to form a substituted or unsubstituted 5 , 6- or 7-membered cycloalkyl or cycloalkenyl ring.
27. The tire of claim 26 , wherein the rubber component is a natural rubber.
28. The tire of claim 22 , wherein the rubber composition further comprises at least one antidegradant.
29. The tire of claim 22 , wherein the rubber composition further comprises at least one compound selected from the group consisting of a phenol, hindered phenol, alkylated diphenylamine, 1,2-dihydro-2,2,4-trimethylquinoline, alkylated hydroquinone, N,N′-bis(alkyl)-para-phenylenediamine, N,N′-bis(aryl)-para-phenylenediamine, N-(alkyl)-N′-(aryl)-para-phenylenediamine, quinonediimine, thioester, phosphite, imidazole, naphthylamine, alkylated naphthylamine, triazine and combinations thereof.
30. A rubber composition comprising a diaryl amine-containing compound represented by the general formula:
wherein n is from 0 to 3; m is from 0 to 3; each R and R 3 substituent is independently hydrogen, a straight branched C 1 -C 32 alkyl group or alkenyl group, substituted or unsubstituted C 3 -C 12 group, substituted or unsubstituted C 5 -C 12 aryl group, hydroxyl-containing group, halogen group, substituted or unsubstituted C 1 -C 20 alkoxy group, ester-containing group, ether-containing group, polyether-containing group, amide-containing group, or amine-containing group or two R substituents and/or two R 3 substituents together with the carbon atom to which they are bonded are joined together to form a substituted or unsubstituted saturated partially saturated or unsaturated C 5 -C 30 ring structure optionally containing one or more heteroatoms;
R 1 and R 2 together with the carbon atom to which they are bonded are joined together to form a substituted or unsubstituted C 5 -C 30 cycloalkyl or cycloalkenyl ring, and
R 4 and R 5 together with the carbon atom to which they are bonded are joined together to form a substituted or unsubstituted C 5 -C 30 cycloalkyl or cycloalkenyl ring, having a rating of about 7.5 according to the Dynamic Ozone Belt Test (ASTM D3395 Method B) and a substantially non-discolored surface after about 394 hours.