IP Library › Patent Application 13224065
Patent Application
App. No. 13/224,065

MODIFIED HYDROCARBYLPHENOL-ALDEHYDE RESINS FOR USE AS TACKIFIERS AND RUBBER COMPOSITIONS CONTAINING THEM

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Patent No.
US None
App. No.
13/224,065
Abstract

The invention relates to a modified hydrocarbylphenol-aldehyde resin prepared by reacting a hydrocarbylphenol-aldehyde resin with a primary or secondary amine and further with an epoxide. The invention also provides a process for preparing a modified, hydrocarbylphenol-aldehyde resin and a rubber composition containing such resin.

Claims (52)

1 . A modified, hydrocarbylphenol-aldehyde resin prepared by reacting an epoxide with a resin of Formula (I) in the presence of a basic catalyst and at a basic pH,

wherein

R 1 is a straight or branched C 1 -C 30 alkyl;

R 2 is —CH 2 R 5 ,

wherein R 5 is an amine of formula (i)

wherein R′ and R″ are independently H, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, aryl, or wherein R′ and R″, together with the N carrying them, form a 5-7 membered heterocyclic ring;

R 3 is R 2 or —CH(R 5 )OH;

R 4 is H or C 1 -C 4 alkyl; and

m plus n is at least 1.

2 . The modified, hydrocarbylphenol-aldehyde resin of claim 1 , wherein said resin is prepared by reacting about 1 to about 25 weight percent the epoxide with the resin of Formula (I).

3 . The modified, hydrocarbylphenol-aldehyde resin of claim 1 , wherein R 5 is morpholinyl.

4 . The modified, hydrocarbylphenol-aldehyde resin of claim 1 , wherein R 1 is a straight or branched C 1 -C 15 alkyl.

5 . The modified, hydrocarbylphenol-aldehyde resin of claim 4 , wherein R 1 is tertiary butyl or tertiary octyl.

6 . A process for preparing a modified, hydrocarbylphenol-aldehyde resin comprising the step of:

(a) reacting an epoxide with a resin of Formula (I) in the presence of a basic catalyst and at a basic pH,

wherein

R 1 is a straight or branched C 1 -C 30 alkyl;

R 2 is —CH 2 R 5 ,

wherein R 5 is an amine of formula (i)

wherein R′ and R″ are independently H, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, aryl, or wherein R′ and R″, together with the N carrying them, form a 5-7 membered heterocyclic ring;

R 3 is R 2 or —CHR 5 OH;

R 4 is H or C 1 -C 4 alkyl; and

m plus n is at least 1.

7 . The process for preparing a modified, hydrocarbylphenol-aldehyde resin according to claim 6 , wherein step (a) comprises reacting about 1 to about 25 weight percent of the epoxide.

8 . The process for preparing a modified, hydrocarbylphenol-aldehyde resin of claim 6 , wherein R 5 is morpholinyl.

9 . The process for preparing a modified, hydrocarbylphenol-aldehyde resin of claim 6 , wherein R 1 is a straight or branched C 1 -C 15 alkyl.

10 . The process for preparing a modified, hydrocarbylphenol-aldehyde resin of claim 9 , wherein R 1 is tertiary butyl or tertiary octyl.

11 . A rubber composition having improved tack, comprising a rubber or mixtures of rubbers, and 0.5 to 7 phr of a modified, hydrocarbylphenol-aldehyde resin of claim 1 .

12 . The rubber composition of claim 11 , wherein R 5 is morpholinyl.

13 . The rubber composition of claim 11 , wherein R 1 is a straight or branched C 1 -C 15 alkyl.

14 . The rubber composition of claim 13 , wherein R 1 is tertiary butyl or tertiary octyl.

15 . The rubber composition of claim 11 , wherein said rubber composition is a 30/70 natural rubber/butadiene rubber composition, a 70/30 styrene butadiene rubber/butadiene rubber composition, or a natural rubber composition.

16 . A modified, hydrocarbylphenol-aldehyde resin prepared by reacting a C 16 alkyl epoxide with a resin of Formula (I) in the presence of a basic catalyst and at a basic pH,

wherein

R 1 is a straight or branched C 1 -C 30 alkyl;

R 2 is —CH 2 R 5 , wherein R 5 is a morpholinyl group;

R 3 is R 2 or —CH(R 5 )OH;

R 4 is H or C 1 -C 4 alkyl; and

m plus n is at least 1.

17 . The modified, hydrocarbylphenol-aldehyde resin of claim 16 , wherein R 1 is tertiary butyl or tertiary octyl.

18 . A rubber composition having improved tack, comprising

a rubber or mixtures of rubbers, and

0.5 to 7 phr of a modified, hydrocarbylphenol-aldehyde resin of claim 16 .

19 . A process for preparing a modified, hydrocarbylphenol-aldehyde resin comprising the step of:

(a) reacting a C 16 alkyl epoxide with a resin of Formula (I) in the presence of a basic catalyst and at a basic pH,

wherein

R 1 is a straight or branched C 1 -C 30 alkyl;

R 2 is —CH 2 R 5 , wherein R 5 is a morpholinyl group;

R 3 is R 2 or —CHR 5 OH;

R 4 is H or C 1 -C 4 alkyl; and

m plus n is at least 1.

20 . The process preparing a modified, hydrocarbylphenol-aldehyde resin of claim 19 , wherein R 1 is tertiary butyl or tertiary octyl.