Rubber composition comprising a thiazoline derivative

Patent metadata

Field	Value
Publication number	US-9550891-B2
Application number	US-201214111606-A
Country	US
Kind code	B2
Filing date	Apr 16, 2012
Priority date	Apr 14, 2011
Publication date	Jan 24, 2017
Grant date	Jan 24, 2017

Abstract

A rubber composition for manufacturing tyres includes one or more diene elastomers, one or more reinforcing fillers, and a vulcanization system. The vulcanization system includes one or more thiazoline compounds chosen from compounds of formula I and compounds of formula II:

Certain specific thiazoline derivatives are described.

First claim

The invention claimed is:

1. 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,
wherein said vulcanization system comprises one or more thiazoline compounds chosen from the compounds of formula

where:
R 1 , R 2 , R′ 1 and R′ 2 independently represent H or a C 1 -C 25 hydrocarbon group chosen from linear, branched or cyclic alkyl groups, aralkyl groups, alkylaryl groups and aryl groups,
R 1 can be combined with R 2 or R′ 2 to form a non-aromatic ring,
R 2 can be combined with R 1 or R′ 1 to form a non-aromatic ring,
A is chosen from H,

where in R 1b is identical to R 1 , R 2b is identical to R 2 , R′ 1b is identical to R′ 1 and R′ 2b is identical to R′ 2 , and x is an integer greater than or equal to 1,

wherein R 3 , R 4 and R 5 independently represent a C 1 -C 18 hydrocarbon group which does not comprise a heteroatom, and y is an integer greater than or equal to 1,

wherein R 6 is a C 1 -C 18 hydrocarbon group, provided that R 1 , R 2 , R′ 1 and R′ 2 do not simultaneously represent H,

wherein R 7 is a C 1 -C 18 hydrocarbon group,

wherein Y is a C 1 -C 18 hydrocarbon chain, and R 8 is a C 1 -C 18 hydrocarbon group,

wherein X is a C 1 -C 18 hydrocarbon chain, and R 9 and R 10 independently represent a C 1 -C 18 hydrocarbon group, and

wherein R 11 is H or a C 1 -C 18 hydrocarbon group,

M n+ represents a metal or non-metal cation, and
n represents an integer varying between 1 and 4.

2. The composition according to claim 1 , wherein R 1 , R 2 , R′ 1 and R′ 2 independently represent H or a methyl group.

3. The composition according to claim 2 , wherein R 1 , R 2 , R′ 1 and R′ 2 each represent H.

4. The composition according to claim 2 , wherein two radicals chosen from R 1 , R 2 , R′ 1 and R′ 2 represent a methyl group, the other two representing H.

5. The composition according to claim 1 , wherein A is

6. The composition according to claim 1 , wherein the R 3 to R 11 groups are independently chosen from linear, branched or cyclic alkyl groups, aryl groups, aralkyl groups and alkylaryl groups.

7. The composition according to claim 1 , wherein the X and Y groups are independently chosen from linear, branched or cyclic alkylene groups, arylene groups and alkylarylene groups.

8. The composition according to claim 1 , wherein M n+ is a metal cation chosen from Zn 2+ , Cu 2+ , Na + , K + and Li + .

9. The composition according to claim 1 , wherein M n+ is a non-metal cation.

10. The composition according to claim 1 , wherein the said thiazoline compound or compounds represent from 0.1 to 7 phr (parts by weight per hundred of diene elastomer).

11. The composition according to claim 1 , wherein the diene elastomer or elastomers are selected from the group consisting of polybutadienes, natural rubber, synthetic polyisoprenes, butadiene copolymers, isoprene copolymers and the mixtures of these elastomers.

12. The composition according to claim 1 , wherein the reinforcing filler or fillers are chosen from silica, carbon black and their mixtures.

13. The composition according to claim 1 , wherein the reinforcing filler or fillers are present at a content of between 20 and 200 phr.

14. A process for preparing a rubber composition for the manufacture of tires according to claim 1 , said process comprising the steps of:
incorporating the reinforcing filler or fillers in the said diene elastomer or elastomers during a first stage, the composition being kneaded thermomechanically, in one or more goes, until a maximum temperature of between 110° C. and 190° C. is reached; and
subsequently incorporating, during a second stage, the crosslinking system and kneading the composition up to a maximum temperature of less than 110° C.

15. The process according to claim 14 , wherein, between the steps, the composition is cooled to a temperature of less than or equal to 100° C.

16. A process of manufacturing a finished article or a semi-finished product comprising the step of:
incorporating a composition according to claim 1 in the finished article or semi-finished product.

17. A finished article or semi-finished product comprising a composition according to claim 1 .

18. A tire comprising a rubber composition according to claim 1 .

19. A tread comprising a rubber composition according to claim 1 .

20. A thiazoline of formula

where:
R 1a , R 2a , R′ 1a and R′ 2a represent H or a C 1 -C 25 hydrocarbon group chosen from linear, branched or cyclic alkyl groups, aralkyl groups, alkylaryl groups and aryl groups,
R 1a can be combined with R 2a , or R′ 2a to form a non-aromatic ring,
R 2a can be combined with R 1a or R′ 1a to form a non-aromatic ring and
A a is chosen from

wherein R 3a , R 4a and R 5a independently represent a C 1 -C 18 hydrocarbon group, and ya is an integer greater than or equal to 1,

wherein R 7a is a C 1 -C 18 hydrocarbon group,

wherein Y a is a C 1 -C 18 hydrocarbon chain, and R 8a is a C 1 -C 18 hydrocarbon group, provided that, if R 1a , R 2a , R′ 1a and R′ 2a simultaneously represent H, Y a is an C 1 -C 10 alkylene chain and R 8a is a C 1 -C 10 alkyl group,

wherein 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, and

wherein R 11a is H or a C 1 -C 18 hydrocarbon group, provided that R 1a , R 2a , R′ 1a and R′ 2a represent a C 1 -C 18 alkyl on a C 3 -C 18 cycloalkyl group.

21. A process of manufacturing a rubber composition based

Assignees

• Veyland Anne
• Seeboth Nicolas
• Michelin & Cie
• Michelin Rech Tech

Inventors

• Veyland Anne
• Seeboth Nicolas

Classifications

• C08K5/0025

  Crosslinking or vulcanising agents; including accelerators · CPC title

• B60C1/0016 Primary

  Compositions of the tread · CPC title

• C08L21/00

  Compositions of unspecified rubbers · CPC title

• C08K5/47

  Thiazoles · CPC title

• C07D277/16

  Sulfur atoms · CPC title