Thiadiazole which can be used as a vulcanization accelerator and method for obtaining same
View Patent ↗A thiadiazole of formula (I):
1. A thiadiazole of formula (I):
where
R 1 represents H or a C 1 -C 25 hydrocarbon group chosen from linear, branched or cyclic alkyl groups and aryl groups which are optionally interrupted by one or more heteroatoms,
R 2 represents:
a cyclic C 3 -C 10 alkyl group which is optionally interrupted by one or more heteroatoms and which is optionally substituted by one or more linear, branched or cyclic C 1 -C 25 alkyl or C 6 -C 12 aryl groups which are optionally interrupted by one or more heteroatoms.
2. The thiadiazole according to claim 1 , wherein R 1 represents H.
3. The thiadiazole according to claim 2 , wherein R 1 represents a methyl group.
4. The thiadiazole according to claim 1 , wherein R 2 represents a cyclohexyl group.
5. A process for the preparation of a thiadiazole as defined in claim 1 , comprising the steps of:
the starting compound is compound (A) of following formula:
where R 1 is as defined in claim 1 ,
compound (A) is reacted with a compound of formula R 2 NH 2 , where R 2 is as defined in claim 1 , in the presence of a base, then
an oxidizing composition comprising at least one oxidizing agent is added to the reaction medium, in order to obtain the thiadiazole of formula (I).
6. The process according to claim 5 , wherein the base is sodium hydroxide.
7. The process according to claim 5 , wherein the oxidizing agent is selected from the group consisting of iodine and sodium hypochlorite.
8. A process comprising a step of incorporating as a vulcanization accelerator, a thiadiazole of formula (I) as defined below, into a rubber composition for the manufacture of tires, based on one or more diene elastomers, on one or more reinforcing fillers, and on a vulcanization system:
where
R 1 represents H or a C 1 -C 25 hydrocarbon group selected from linear, branched or cyclic alkyl groups and aryl groups which are optionally interrupted by one or more heteroatoms,
R 2 represents:
a linear C 2 -C 25 or branched C 3 or C 5 -C 25 alkyl group which is optionally interrupted by one or more heteroatoms and which is optionally substituted by one or more cyclic C 3 -C 10 alkyl or C 6 -C 12 aryl groups, or
a cyclic C 3 -C 10 alkyl group which is optionally interrupted by one or more heteroatoms and which is optionally substituted by one or more linear, branched or cyclic C 1 -C 25 alkyl or C 6 -C 12 aryl groups which are optionally interrupted by one or more heteroatoms.
9. The process according to claim 5 , wherein the oxidizing composition is an aqueous sodium hypochlorite solution.
10. A thiadiazole of formula (I):
where
R 1 represents H,
R 2 represents:
a linear C 2 -C 25 or branched C 3 or C 5 -C 25 alkyl group which is optionally interrupted by one or more heteroatoms and which is optionally substituted by one or more cyclic C 3 -C 10 alkyl or C 6 -C 12 aryl groups, or
a cyclic C 3 -C 10 alkyl group which is optionally interrupted by one or more heteroatoms and which is optionally substituted by one or more linear, branched or cyclic C 1 -C 25 alkyl or C 6 -C 12 aryl groups which are optionally interrupted by one or more heteroatoms.