Rubber composition comprising a 1,3-dipolar compound additive bearing an imidazole functional group

Patent metadata

Field	Value
Publication number	US-10137734-B2
Application number	US-201415031407-A
Country	US
Kind code	B2
Filing date	Oct 24, 2014
Priority date	Oct 25, 2013
Publication date	Nov 27, 2018
Grant date	Nov 27, 2018

Abstract

A rubber composition is based on at least one diene elastomer, a reinforcing filler and a 1,3-dipolar compound bearing an imidazole functional group. Such a composition exhibits an improved compromise in certain properties such as stiffness in the cured state and hysteresis.

First claim

The invention claimed is:

1. A rubber composition based on:
at least one diene elastomer;
a reinforcing filler; and
a 1,3-dipolar compound of formula (I):
Q-A-B  (I)

wherein Q comprises a dipole containing at least one nitrogen atom,
wherein A is an atom or a group of atoms connecting Q to B,
wherein B comprises a ring of formula (II):

 and
wherein three of the four symbols Z, Y, R and R′, which are identical or different, each represent an atom or a group of atoms, it being possible for Z and Y to form, together with the carbon atoms to which they are attached, a ring, and the fourth symbol Z, Y, R or R′ denotes a direct attachment to A.

2. The rubber composition according to claim 1 , wherein R′ denotes a direct attachment to A.

3. The rubber composition according to claim 2 , wherein Z and Y are each a hydrogen atom.

4. The rubber composition according to claim 2 , wherein Z and Y form, together with the carbon atoms to which they are attached, a ring.

5. The rubber composition according to claim 1 , wherein R represents a hydrogen atom or a carbon-based group which can contain at least one heteroatom.

6. The rubber composition according to claim 5 , wherein R is an alkyl group that contains from 1 to 12 carbon atoms.

7. The rubber composition according to claim 1 , wherein A is an aliphatic group or an aromatic group.

8. The rubber composition according to claim 7 , wherein A is an alkylene group containing from 1 to 20 carbon atoms or an arylene group.

9. The rubber composition according to claim 1 , wherein the 1,3-dipolar compound is selected from the group consisting of nitrile oxides, nitrile imines and nitrones.

10. The rubber composition according to claim 9 , wherein Q contains a —C≡N→O unit.

11. The rubber composition according to claim 10 , wherein Q comprises a unit of formula (III):

wherein four of the five symbols R 1 to R 5 , which are identical or different, are each an atom or a group of atoms, and the fifth symbol denotes a direct attachment to A, and
wherein R 1 and R 5 are not H.

12. The rubber composition according to claim 11 , wherein R 1 , R 3 and R 5 are each an alkyl group of 1 to 6 carbon atoms.

13. The rubber composition according to claim 12 , wherein the 1,3-dipolar compound is 2,4,6-trimethyl-3 -((2-methyl-1H-imidazol-1-yl)methyl)benzonitrile oxide or 2,4,6-triethyl-3-((2-methyl-1H-imidazol-1-yl)methyl)benzonitrile oxide.

14. The rubber composition according to claim 9 , wherein Q contains a —C═N(→O)— unit.

15. The rubber composition according to claim 14 , wherein Q comprises a unit of formula (IV) or (V):

wherein Y 1 is an aliphatic group or an aromatic group containing from 6 to 20 carbon atoms, and
wherein Y 2 , comprising a direct attachment to A, is an aliphatic group or an aromatic group comprising, on its benzene nucleus, the direct attachment to A.

16. The rubber composition according to claim 15 , wherein the 1,3-dipolar compound is of formula (IVa), (IVb), (Va) or (Vb):

17. The rubber composition according to claim 1 , wherein an amount of 1,3-dipolar compound is between 0 and 3 molar equivalents of imidazole ring per 100 moles of monomer units constituting the diene elastomer.

18. The rubber composition according to claim 1 , wherein the diene elastomer is an essentially unsaturated elastomer selected from the group consisting of polybutadienes, polyisoprenes, butadiene copolymers, isoprene copolymers and mixtures thereof.

19. The rubber composition according to claim 1 , wherein the reinforcing filler comprises an organic filler.

20. The rubber composition according to claim 1 , wherein the reinforcing filler comprises a reinforcing inorganic filler.

21. The rubber composition according to claim 20 , wherein the reinforcing inorganic filler is a silica.

22. The rubber composition according to claim 20 , wherein the rubber composition further comprises a silane coupling agent for bonding the reinforcing inorganic filler to the diene elastomer.

23. The rubber composition according to claim 1 , wherein the rubber composition further comprises a crosslinking system.

24. A tread which comprises a rubber composition according to claim 1 .

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

26. A process for preparing a rubber composition according to claim 23 , said process comprising the steps of:
adding, during a first non-productive stage, to the diene elastomer, the 1,3-dipolar compound, the reinforcing filler and, if appropriate, a coupling agent, by kneading thermomechanically until a maximum temperature of between 130° C. and 200° C. is reached;
cooling the combined mixture to a temperature of less than 100° C.;
subsequently incorporating the crosslinking system; and
kneading up to a maximum temperature of less than 120° C.

Assignees

• Michelin & Cie
• Michelin Rech Tech

Inventors

• Gander Sophie
• Salit Anne-Frédérique
• Seeboth Nicolas

Classifications

• C08K3/36

  Silica · CPC title

• B60C1/0016 Primary

  Compositions of the tread · CPC title

• B60C1/00

  Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition · CPC title

• B60C11/0008

  characterised by the tread rubber · CPC title

• C08C19/22

  Incorporating nitrogen atoms into the molecule · CPC title