IP Library Granted Patent US 9,663,633
Granted Patent B2
US 9,663,633 · App. 14/377,023 · Granted May 30, 2017

Composition based on natural rubber and on a polyaldimine compound

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Quick Facts
Patent No.
US 9,663,633
App. No.
14/377,023
Granted
May 30, 2017
Kind
B2
Abstract

A reinforced rubber composition based at least on an elastomeric matrix comprising natural rubber, on a reinforcing filler and on a polyaldimine compound of general formula (I), in which the R 1 , R 2 and A elements are variable groups. This composition is intended in particular for the manufacture of semi-finished products for tires.

Claims (32)

1. A reinforced rubber composition based at least on an elastomeric matrix comprising natural rubber, said natural rubber present in said elastomeric matrix in an amount of from over 50 phr to 100 phr, a reinforcing filler present in an amount of from 35 to 200 phr in said elastomeric matrix and a polyaldimine compound of general formula (I):

wherein:

R 1 and R 2 independently represent identical or different groups chosen from alkyl groups having from 1 to 20 carbon atoms, cycloalkyl groups having from 5 to 24 carbon atoms, aryl groups having from 6 to 30 carbon atoms or aralkyl groups having from 7 to 25 carbon atoms; which groups can optionally be interrupted by heteroatoms and/or substituted,

A represents a hydrocarbon group comprising at least 3 carbon atoms, optionally interrupted by heteroatoms and optionally substituted, wherein the A group does not represent an aromatic nucleus directly bonded to the structure of the compound of general formula (I),

wherein the polyaldimine compound is chosen from the following compounds:

N,N′-bis[phenylmethylene]hexane-1,6-diamine,

N,N′-bis[phenylmethylene]octane-1,8-diamine,

N,N′-bis[phenylmethylene]cyclohexane-1,4-diamine,

N,N′-bis[phenylmethylene]cyclohexane-1,2-diamine,

N,N,N-tris(2-{[phenylmethylene]amino}ethyl)amine,

N,N′-bis[(4-diethylaminophenyl)methylene]hexane-1,6-diamine,

N,N′-bis[(4-methoxyphenyl)methylene]hexane-1,6-diamine,

N,N′-bis[(2-diethylaminophenyl)methylene]hexane-1,6-diamine,

N,N′-bis[(2-methoxyphenyl)methylene]hexane-1,6-diamine,

N,N′-bis[mesitylmethylene]hexane-1,6-diamine,

N,N′-bis[(4-methylphenyl)methylene]hexane-1,6-diamine,

N,N′-bis[(2,4,6-triisopropylphenyl)methylene]hexane-1,6-diamine,

N,N′-bis[(2,4,6-tri {tert-butyl}phenyl)methylene]hexane-1,6-diamine,

N,N′-bis[(2,4,6-tricyclohexylphenyl)methylene]hexane-1,6-diamine,

N,N′-bis[(2,6-diisopropyl-4-methylphenyl)methylene]hexane-1,6-diamine,

N,N′-bis[(2,6-di{tert-butyl}-4-methylphenyl)methylene]hexane-1,6-diamine,

N,N′-bis[(2,6-dicyclohexyl-4-methylphenyl)methylene]hexane-1,6-diamine,

N,N′-bis[(4-diethylaminophenyl)methylene]octane-1,8-diamine,

N,N′-bis[mesitylmethylene]octane-1,8-diamine, and

N,N′-bis[(4-methylphenyl)methylene]octane-1,8-diamine, and

wherein said polyaldimine compound is present at a level of from 0.1 to 20 millimoles per 100 grams of elastomeric matrix and said reinforcing filler comprises at least one inorganic reinforcing filler and a coupling agent, said inorganic reinforcing filler having hydroxyl groups, said coupling agent comprising at least one functional group that bonds to said hydroxyl groups of said inorganic reinforcing filler and at least one functional group that bonds to said natural rubber.

2. The rubber composition according to claim 1 , wherein the natural rubber content is 100 phr.

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

4. The rubber composition according to claim 1 , wherein the coupling agent is present in an amount of less than 20 phr.

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

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

7. A tire, comprising a semi-finished product according to claim 6 .

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 8, 2020
From: MICHELIN RECHERCHE ET TECHNIQUE S.A.
To: COMPAGNIE GENERALE DES ETABLISSEMENTS MICHELIN
Reel/Frame 052863/0624 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 29, 2014
From: MOUGIN, CATHERINE; BELZ, JUSTIN; ARAUJO DA SILVA, JOSE CARLOS
To: COMPAGNIE GENERALE DES ETABLISSEMENTS MICHELIN; MICHELIN RECHERCHE ET TECHNIQUE S.A.
Reel/Frame 033839/0248 →