Rubber composition including a 1,2,4-triazine derivative
View Patent ↗A rubber composition for manufacturing tyres is based on one or more diene elastomers, one or more reinforcing fillers, and a vulcanization system. The vulcanization system includes one or more 1,2,4-triazine compounds chosen from compounds of formula I and compounds of formula II: Certain specific 1,2,4-triazine derivatives are described.
1. A rubber composition used in manufacturing tyres the composition comprising:
one or more diene elastomers;
one or more reinforcing fillers; and
a vulcanization system, wherein the vulcanization system includes one or more 1,2,4-triazine compounds selected from compounds of formula
where:
R 1 and R 2 independently represent H, a halogen, a group selected from alkoxy and (C1-C10)alkylthio groups, or a C 1 -C 25 hydrocarbon group selected from a group consisting of linear, branched, or cyclic alkyl groups, aralkyl groups, alkylaryl groups, and aryl groups, R 1 and R 2 being formable in a ring,
A is selected from
—H,
a group
where:
R′ 1 is same as R 1 ,
R′ 2 is same as R 2 ,
x is an integer greater than or equal to 1,
a group
←S y —R 3
where
R 3 represents a C 1 -C 18 hydrocarbon group,
y is an integer greater than or equal to 1,
a group
where R 6 is a C 1 -C 18 hydrocarbon group,
a group
where R 7 is a C 1 -C 18 hydrocarbon group,
a group
where
Y is a C 1 -C 18 hydrocarbon chain;
R 8 is a C 1 -C 18 hydrocarbon group,
a group
where
X is a C 1 -C 18 hydrocarbon chain;
R 9 and R 10 independently represent a C 1 -C 18 hydrocarbon group, and
a group
where
R 11 is H or a C 1 -C 18 hydrocarbon group,
M n+ represents a metal or non-metal cation,
n represents an integer between 1 and 4.
2. The composition according to claim 1 , wherein R 1 and R 2 independently represent H or a phenyl group.
3. The composition according to claim 2 , wherein R 2 represents a phenyl group and R 1 represents H.
4. The composition according to claim 1 , wherein A is selected from
the group
the group
←S y —R 3
the group
the group
where x, R′ 1 , R′ 2 , y, R 3 , X, R 9 , R 10 and R 11 are as defined in claim 1 .
5. The composition according to claim 1 , wherein the R 3 and R 6 to R 11 groups are independently selected from a group consisting of linear, branched, or cyclic alkyl groups, aryl groups, aralkyl groups, and alkylaryl groups.
6. The composition according to claim 1 , wherein the X and Y groups are independently selected from a group consisting of linear, branched, or cyclic alkylene groups, arylene groups, and alkylarylene groups.
7. The composition according to claim 1 , wherein the the M n+ is a metal cation selected from a group consisting of Zn 2+ , Cu 2+ , Na + , K + , and Li + .
8. The composition according to claim 1 , wherein M n+ is a non-metal cation.
9. The composition according to claim 1 , wherein the 1,2,4-triazine compound or compounds represent from 0.1 to 7 phr (parts by weight per hundred parts of diene elastomer).
10. The composition according to claim 1 , wherein the diene elastomer or elastomers are selected from a group of elastomers consisting of polybutadienes, natural rubber, synthetic polyisoprenes, butadiene copolymers, isoprene copolymers, and mixtures of these elastomers.
11. The composition according to claim 1 , wherein the reinforcing filler or fillers are selected from a group consisting of silica, carbon black, and their mixtures.
12. The composition according to claim 1 , wherein the reinforcing filler or fillers are present at a content of between 20 and 200 phr.
13. A process for preparing a rubber composition as defined in claim 1 , used in manufacturing tyres, the process comprising steps of:
incorporating the reinforcing filler or fillers in the diene elastomer or elastomers during a first stage and kneading thermomechanically, in one or more goes, until a maximum temperature of between 110° C. and 190° C. is reached;
subsequently incorporating, during a second stage, the vulcanization system and kneading up to a maximum temperature of less than 110° C.
14. The process according to claim 13 , wherein, between the kneading thermomechanically and the incorporating of the vulcanization system, a combined product of the kneading thermomechanically is cooled to a temperature of less than or equal to 100° C.
15. The composition according to claim 1 , wherein the composition is used in manufacturing a finished article or a semi-finished product intended for a motor vehicle ground-contact system.
16. A tyre comprising the rubber composition as defined in claim 1 .
17. A tread comprising the rubber composition as defined in claim 1 .
18. A 1,2,4-triazine of formula
where:
R 1a and R 2a independently represent H, a halogen, a group selected from alkoxy and (C 1 -C 10 )alkylthio groups, or a C 1 -C 25 hydrocarbon group selected from a group consisting of linear, branched, or cyclic alkyl groups, aralkyl groups, alkylaryl groups, and aryl groups, R 1a and R 2a being formable in a ring,
A a is selected from
a group
←S ya —R 3a
where
R 3a represents a C 1 -C 18 hydrocarbon group that does not include 1,2,4-triazine, wherein a compound of the formula (I′) is not of formula
y a is an integer greater than or equal to 1,
a group
where R 6a is a C 1 -C 18 hydrocarbon group other than a substituted phenyl group, wherein, if R 6a represents a methyl group, R 1a and R 2a do not form a ring and R 1a and R 2a respectively do not represent a methyl and a hydroxyl,
group
where R 7a is a C 1 -C 18 hydrocarbon group, wherein, if R 7a represents an ethyl group, R 1a and R 2a do not form a ring,
a group
where
X a is a C 1 -C 18 hydrocarbon chain, and
R 9a and R 10a independently represent a C 1 -C 18 hydrocarbon group.
19. The 1,2,4-triazine according to claim 18 , wherein R 1a and R 2a independently represent H or a phenyl group.
20. The 1,2,4-triazine according to claim 19 , wherein R 2a represents a phenyl group and R 1a represents H.
21. The 1,2,4-triazine according to claim 18 , wherein A a is selected from:
the group
←S ya —R 3a
and
the group
wherein y a , R 3a , X a , R 9a , and R 10a are as defined in claim 18 .
22. The 1,2,4-triazine according to claim 18 , wherein the R 3a , R 6a , R 7a , and R 9a to R 10a groups are independently selected from a group consisting of linear, branched, or cyclic alkyl groups, aryl groups, aralkyl groups, and alkylaryl groups.
23. The 1,2,4-triazine according to claim 18 , wherein the X a group is selected from a group consisting of linear, branched, or cyclic alkylene groups, arylene groups, and alkylarylene groups.