Use of an esterified aromatic polyphenol derivative for the production of a phenol-aldehyde resin for reinforcement of a rubber composition

Patent metadata

Field	Value
Publication number	US-10711132-B2
Application number	US-201615762759-A
Country	US
Kind code	B2
Filing date	Sep 23, 2016
Priority date	Sep 25, 2015
Publication date	Jul 14, 2020
Grant date	Jul 14, 2020

Abstract

An aromatic polyphenol derivative which comprises at least one aromatic ring bearing at least two —O—Z groups in the meta position relative to one another, the two positions ortho to at least one of the —O—Z groups being unsubstituted, is used for the manufacture of a phenol-aldehyde resin for reinforcing a rubber composition. Each —O—Z group represents an —O—((C═O)(R1)) group with R1 representing a hydrocarbon-based radical or a substituted hydrocarbon-based radical.

First claim

The invention claimed is:

1. A method for the manufacture of a phenol-aldehyde resin for reinforcing a rubber composition comprising the steps of:
mixing at least one aldehyde and an aromatic polyphenol derivative, wherein the aromatic polyphenol derivative is selected from the group consisting of the aromatic polyphenol derivatives (IV), (V), and mixtures thereof, the aromatic rings bearing at least two —O—Z groups in the meta position relative to one another, the two positions ortho to at least one of the —O—Z groups being unsubstituted, and each —O—Z group representing an —O—((C═O)(R 1 )) group with R 1 representing a hydrocarbon-based radical or a substituted hydrocarbon-based radical,

and
crosslinking the aromatic polyphenol derivative and the at least one aldehyde to produce the phenol-aldehyde resin.

2. The method according to claim 1 , wherein the crosslinking step occurs after a delay phase generated by the aromatic polyphenol.

3. The method according to claim 1 , wherein using the aromatic polyphenol derivative in a phenol-aldehyde resin maintains stiffness of a rubber composition with an increase in temperature.

4. The method according to claim 1 , wherein the aromatic aldehyde is selected from the group consisting of 1,3-benzenedicarboxaldehyde, 1,4-benzenedicarboxaldehyde and an aldehyde of formula

in which X comprises N, S or O; R represents —H or —CHO, and mixtures thereof.

5. The method according to claim 1 , wherein the aromatic aldehyde is selected from the group consisting of 1,4-benzenedicarboxaldehyde, furfuraldehyde, 2,5-furandicarboxaldehyde and mixtures thereof.

6. The method according to claim 1 , wherein R 1 represents a radical selected from the group consisting of alkyl, aryl, arylalkyl, alkylaryl, cycloalkyl and alkenyl radicals.

7. The method according to claim 1 , wherein R 1 represents a radical comprising a single carbon atom.

8. The method according to claim 1 , wherein R 1 represents a methyl radical.

9. The method according to claim 1 , wherein R 1 comprises at least two carbon atoms.

10. The method according to claim 1 , wherein R 1 represents an alkyl radical.

11. The method according to claim 1 , wherein R 1 comprises at most four carbon atoms.

12. The method according to claim 1 , wherein R 1 comprises at least five carbon atoms.

13. The method according to claim 1 , wherein R 1 comprises at least 10 carbon atoms.

14. The method according to claim 1 , wherein R 1 comprises at least 15 carbon atoms.

15. The method according to claim 1 , wherein R 1 comprises at most 30 carbon atoms.

16. The method according to claim 1 , wherein R 1 comprises at most 25 carbon atoms.

17. The method according to claim 1 , wherein R 1 comprises at most 20 carbon atoms.

Assignees

• Michelin & Cie

Inventors

• Thuilliez Anne-Lise
• Gavard-Lonchay Odile
• Loubat Cedric
• Boutevin Gilles
• Crouzet Quentin

Classifications

• C08G8/06

  of furfural · CPC title

• C08G8/32

  by organic acids or derivatives thereof, e.g. fatty oils · CPC title

• B60C1/0041

  Compositions of the carcass layers · CPC title

• C08L7/00

  Compositions of natural rubber · CPC title

• C08G8/04

  of aldehydes · CPC title