IP Library Granted Patent US 9,566,828
Granted Patent B2
US 9,566,828 · App. 13/383,179 · Granted Feb 14, 2017

Composition based on natural rubber and a polyimine compound

Inventors: José Carlos Araujo Da Silva (Pont du Chateau, FR); Justin Belz (Riom, FR)
Assignees: MICHELIN RECHERCHE ET TECHNIQUE S.A.; COMPAGNIE GENERALE DES ETABLISSEMENTS MICHELIN
B60C1/0016C08K5/29C08L21/00
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Quick Facts
Patent No.
US 9,566,828
App. No.
13/383,179
Granted
Feb 14, 2017
Kind
B2
Abstract

Reinforced rubber composition based on, exhibiting a lesser hysteresis degradation over time, based on at least (a) an elastomeric matrix predominantly based on natural rubber, (b) a reinforcing filler and (c) a specific polyimine compound in a content of between 6 and 20 mmol per 100 g of elastomer. This rubber composition is intended, for example, for the manufacture of a semi-finished rubber product intended for the tyres of motor vehicles.

Claims (21)

1. A rubber composition based at least:

(a) on an elastomeric matrix comprising non-halogenated natural rubber, wherein the weight fraction of natural rubber in the elastomeric matrix is greater than or equal to 50% by weight of the total weight of the matrix,

(b) on a reinforcing filler, and

(c) on a polyimine compound, in a proportion ranging from 6 to 20 mmol per 100 g of elastomer, wherein the polyimine compound is selected from the group consisting of N,N′-bis(4-methylpentan -2-ylidene)hexane-1,6-diamine, N,N′-bis(2,6-dimethylheptan-4-ylidene)hexane-1,6-diamine, N,N′-bis(2,4-dimethylpentan-3-ylidene)hexane-1,6-diamine, N,N′-bis(4-methylpentan-2-ylidene)octane-1,8-diamine, N,N′-bis(2,6-dimethylheptan-4-ylidene)octane-1,8-diamine, N,N′-bis(2,4-dimethylpentan-3-ylidene)octane-1,8-diamine, N,N′-dicyclopentylidenehexane-1,6-diamine, N,N′-dicyclopentylideneoctane-1,8-diamine, N,N′-dicyclohexylidenehexane -1,6-diamine, N,N′-dicyclohexylideneoctane-1,8-diamine, N,N′-bis(4-methylpentan-2-ylidene)cyclohexane-1,4-diamine, N,N′-bis(4-methylpentan-2-ylidene)cyclohexane-1,2-diamine, N,N′-bis(2,6-dimethylheptan-4-ylidene)cyclohexane-1,4-diamine, N,N′-bis(2,6-dimethylheptan-4-ylidene)cyclohexane-1,2-diamine, N,N′-dicyclohexylidenecyclohexane-1,4-diamine, N,N′-dicyclohexylidenecyclohexane-1,2-diamine, N-(4-methylpentan-2-ylidene)-,N′,N′-bis((4-methylpentan-2-ylideneamino)ethyl)ethane-1,2-diamine and N-(2,6-dimethylheptan-4-ylidene)-N′,N′-bis(2-(2,6-dimethylheptan-4-ylideneamino) ethyl)ethane-1,2-diamine.

2. A rubber composition according to claim 1 , wherein the elastomeric matrix consists of 100% natural rubber.

3. A rubber composition according to claim 1 , wherein the reinforcing filler comprises an organic filler in a proportion of 100% by weight of the total weight of the filler.

4. A rubber composition according to claim 3 , wherein the organic filler is carbon black.

5. A rubber composition according to claim 1 , wherein the reinforcing filler comprises an inorganic filler and wherein it also comprises a coupling agent.

6. A rubber composition according to claim 5 , wherein the inorganic filler is a reinforcing silica.

7. A rubber composition according to claim 1 , wherein the reinforcing filler comprises a reinforcing inorganic filler in proportions ranging from 55% to 100% by weight of the total weight of the filler.

8. A rubber composition according to claim 1 , wherein the polyimine compound is present in a proportion ranging from 6 to 16 mmol per 100 g of elastomer.

9. A rubber composition according to claim 1 , wherein the polyimine compound is selected from the group consisting of N,N′-bis(4-methylpentan-2-ylidene)hexane-1,6-diamine; N,N′-bis(4-methylpentan-2-ylidene)cyclohexane-1,4-diamine; and N,N′-bis(4-methylpentan-2-ylidene)cyclohexane-1,2-diamine.

10. A rubber composition according to claim 1 , wherein the rubber composition includes a crosslinking system.

11. A process for the preparation of a reinforced rubber composition as described in claim 1 , comprising the following stages:

(i) carrying out, at a maximum temperature of between 130° C. and 200° C., a first step of thermomechanical working of at least the elastomeric matrix and the reinforcing filler of the rubber composition, with the exception of a crosslinking system, by incorporating, ingredients of the composition in the elastomeric matrix based on natural rubber, then

(ii) carrying out, at a temperature lower than said maximum temperature of said first step, a second step of mechanical working during which said crosslinking system is incorporated, wherein the addition of the polyimine compound is carried out during the abovementioned stage (ii).

12. A preparation process according to claim 11 , wherein the polyimine compound is added in a high content ranging from 6 to 20 mmol per 100 g of elastomer.

13. A preparation process according to claim 12 , wherein the polyimine compound is added in a proportion ranging from 6 to 16 mmol per 100 g of elastomer.

14. A process for improving, over time, the hysteresis properties of a tire, comprising the incorporation, during the manufacture of this tire, of a reinforced rubber composition prepared in accordance with claim 11 .

15. A tire semi-finished rubber product, comprising a crosslinkable or crosslinked rubber composition according to claim 1 .

16. A tire comprising a semi-finished product according to claim 15 .

Assignments (3)
MERGER Recorded Sep 27, 2012
From: SOCIETE DE TECHNOLOGIE MICHELIN
To: COMPAGNIE GENERALE DES ETABLISSEMENTS MICHELIN
Reel/Frame 029040/0860 →
CORRECTIVE ASSIGNMENT TO CORRECT THE NAME OF THE FIRST ASSIGNOR FROM "ARAUJO DA SILVA, JOSE CARLOW" TO --ARAUJO DA SILVA, JOSE CARLOS PREVIOUSLY RECORDED ON REEL 027884 FRAME 0970. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded May 24, 2012
From: ARAUJO DA SILVA, JOSE CARLOS; BELZ, JUSTIN
To: SOCIETE DE TECHNOLOGIE MICHELIN; MICHELIN RECHERCHE ET TECHNIQUE S.A.
Reel/Frame 028274/0618 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 19, 2012
From: ARAUJO DA SILVA, JOSE CARLOW; BELZ, JUSTIN
To: SOCIETE DE TECHNOLOGIE MICHELIN; MICHELIN RECHERCHE ET TECHNIQUE S.A.
Reel/Frame 027884/0970 →
Priority Claims (1)
FR 09/03436 · Jul 10, 2009 · national
Continuity (1)
Related Publication 20120165449A1 · Jun 28, 2012