IP Library Granted Patent US 7,294,684
Granted Patent B2
US 7,294,684 · App. 11/558,902 · Granted Nov 13, 2007

Dimeric and polymeric alkylphenol polysulfides

Assignee: Dover Chemical Corporation
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Quick Facts
Patent No.
US 7,294,684
App. No.
11/558,902
Granted
Nov 13, 2007
Kind
B2
Abstract

The invention relates to a process and composition-of-matter for the preparation of dimeric and polymeric alkylphenol polysulfides based on paracumyl phenol for use in vulcanizable rubbers in which the additive is a dimeric or polymeric alkylphenol polysulfide non-nitrosamine-releasing additive based on paracumyl phenol.

Claims (28)

1. A process for maintaining or improving physical properties of a vulcanizable rubber by the incorporation of a non-nitrosamine-releasing compound comprising a di- and poly- sulfide having a composition illustrated by formula (I)

wherein

R is a independently selected from the group consisting of H, C 1-9 alkyls, C 1-9 aryls, C 1-14 alkylaryls, C 1-14 arylalkyls, and halogens,

n is an integral value from 0 to 10;

a is an integral value from 0 to 3 inclusive;

b is an integral value from 0 to 5 inclusive;

y is an integral value from 0 to 2; and

z is an integral value from 0 to 5.

2. The process of claim 1 wherein said non-nitrosamine releasing compound is added at 0.5 to 20 phr inclusive.

3. The process of claim 2 wherein said non-nitrosamine releasing compound is added at 1 to 10 phr inclusive.

4. The process of claim 3 wherein said non-nitrosamine releasing compound is added at 2 phr.

5. The process of claim 1 wherein said maintaining or improving in physical properties of said rubber is selected from the group consisting of reduction in premature vulcanization, lower tack, lower volatility, lower volatile degradation, improved heat aging properties, increase in green tack, improved additive dispersability over said rubber which does not include said non-nitrosamine-releasing compound.

6. The process of claim 5 wherein said maintaining or improving in physical properties is a reduction in premature vulcanization or scorching.

7. A process for synthesizing alkylarylphenol polysulfides comprising the steps of:

(a) adding p-cumylphenol to a solvent;

(b) adding sulfur monochloride to said solvent;

(c) heating said p-cumylphenol and sulfur monochloride and solvent; and

(d) removing at least some of said solvent.

8. The process of claim 7 which further comprises the step of adding elemental sulfur during said reaction of p-cumylphenol and sulfur monochloride.

9. The process of claim 8 which further comprises the step of adding stearic acid.

10. The process of claim 7 wherein said solvent is selected from the group consisting of toluene, xylene and benzene.

11. The process of claim 7 wherein said solvent is selected from the group consisting of toluene and xylene.

12. A process for maintaining or improving physical properties of a vulcanizable rubber by the incorporation of a non-nitrosamine-releasing compound comprising a di-sulfide having a composition illustrated by formula (II)

13. The process of claim 12 wherein said non-nitrosamine releasing compound is added at 05 to 20 phr inclusive.

14. The process of claim 13 wherein said non-nitrosamine releasing compound is added at 1 to 10 phr inclusive.

15. The process of claim 14 wherein said non-nitrosamine releasing compound is added at 2 phr.

16. The process of claim 12 wherein said maintaining or improving in physical properties of said rubber is selected from the group consisting of reduction in premature vulcanization, lower tack, lower volatility, lower volatile degradation, improved heat aging properties, increase in green tack, improved additive dispersability over said rubber which does not include said non-nitrosamine-releasing compound.

17. The process of claim 16 wherein said maintaining or improving in physical properties is a reduction in premature vulcanization or scorching.

Assignments (3)
SECURITY INTEREST Recorded Jan 19, 2017
From: DOVER CHEMICAL CORPORATION
To: WELLS FARGO BANK, NATIONAL ASSOCIATION
Reel/Frame 041021/0849 →
SECURITY AGREEMENT Recorded Mar 10, 2011
From: DOVER CHEMICAL CORPORATION; KEIL CHEMICAL CORPORATION
To: THE HUNTINGTON NATIONAL BANK
Reel/Frame 025921/0382 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 1, 2007
From: STEVENSON, DONALD R., MR.; KODALI, SATYAN, MR.; NGUYEN, DUONG N., MR.
To: DOVER CHEMICAL CORPORATION
Reel/Frame 018838/0566 →
Continuity (2)
Provisional Application 6059712400 · Nov 11, 2005
Related Publication 20070093613A1 · Apr 26, 2007