IP Library Granted Patent US 8,030,418
Granted Patent B2
US 8,030,418 · App. 11/849,753 · Granted Oct 4, 2011

Modified hydrocarbylphenol-aldehyde resins for use as tackifiers and rubber compositions containing them

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Quick Facts
Patent No.
US 8,030,418
App. No.
11/849,753
Granted
Oct 4, 2011
Kind
B2
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 (39)

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 the 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 wherein the epoxide is an epoxide prepared from a C 4 -C 60 α-olefin.

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

3. The modified, hydrocarbylphenol-aldehyde resin of claim 1 , wherein the epoxide is a straight-chain C 4 -C 22 alkyl epoxide.

4. The modified, hydrocarbylphenol-aldehyde resin of claim 3 , wherein the epoxide is a straight-chain C 6 -C 16 alkyl epoxide.

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

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

7. The modified, hydrocarbylphenol-aldehyde resin of claim 6 , wherein R 1 is tertiary butyl or tertiary octyl.

8. 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 the 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 wherein the epoxide is an epoxide prepared from a C 4 -C 60 α-olefin.

9. A process for preparing a modified, hydrocarbylphenol-aldehyde resin according to claim 8 , wherein step (a) comprises reacting about 1 to about 25 weight percent of the epoxide.

10. 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 .

11. The rubber composition of claim 10 , wherein said hydrocarbylphenol-aldehyde resin ranges from 1 to 4 phr.

12. The rubber composition of claim 10 , wherein said hydrocarbylphenol-aldehyde resin is prepared by reacting about 1 to about 25 weight percent of an epoxide with a resin of Formula (I).

13. The rubber composition of claim 10 , wherein said epoxide is a straight-chain C 4 -C 22 alkyl epoxide.

14. The rubber composition of claim 13 , wherein said epoxide is a straight-chain C 6 -C 16 alkyl epoxide.

15. The rubber composition of claim 10 , wherein the epoxide is a C 16 alkyl epoxide.

16. The modified, hydrocarbylphenol-aldehyde resin of claim 1 , wherein the epoxide is a C 16 alkyl epoxide.

17. The rubber composition of claim 10 , wherein R 5 is morpholinyl.

18. The rubber composition of claim 10 , wherein R 1 is a straight or branched C 1 -C 15 alkyl.

19. The rubber composition of claim 18 , wherein R 1 is tertiary butyl or tertiary octyl.

20. The rubber composition of claim 10 , 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.

Assignments (3)
RELEASE OF SECURITY INTEREST Recorded Nov 1, 2024
From: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: SI GROUP, INC.; ADDIVANT USA, LLC; SI GROUP USA (USAA), LLC (F/K/A ADDIVANT USA, LLC)
Reel/Frame 069290/0057 →
SECURITY INTEREST Recorded Nov 16, 2018
From: SI GROUP, INC.; ADDIVANT USA, LLC
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 048822/0965 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 14, 2008
From: BANACH, TIMOTHY E.; HOWARD, L. SCOTT; MAKENZIE, TODD SCOTT; SMITH, RONALD K.
To: SI GROUP, INC.
Reel/Frame 020361/0468 →