IP Library Granted Patent US 8,481,657
Granted Patent B2
US 8,481,657 · App. 13/143,867 · Granted Jul 9, 2013

Increased monomer conversion in emulsion polymerization

Inventors: Hans A. Edel (Erdeborn, DE); Hagen Bartossek (Sachsen-anhalt, DE); Doris R. Marx (Merseburg, DE)
Assignee: Styron Europe GmbH
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 8,481,657
App. No.
13/143,867
Granted
Jul 9, 2013
Kind
B2
Abstract

A method for increasing the monomer conversion in a redox initiated emulsion polymerization has been discovered. The method comprises adding a composition comprising an effective amount of a substituted phenol to the polymerization medium. In this manner, high monomer conversion is obtained and the product has low gel contents and a low amount or no crosslinking.

Claims (16)

1. A method for increasing the monomer conversion in a redox initiated emulsion polymerization wherein said method comprises adding a composition comprising an effective amount of a substituted phenol to the polymerization medium, wherein the substituted phenol is selected from the group consisting of 2-6-di-t-butyl para-cresol; 2,6-bis(1,1-dimethylethyl)-4-methylphenol; octadecyl-3-(3,5-di-t-butyl-4-hydroxyphenyl)proprionate; benzenepropionic acid, 3,5-bis((1,1-dimethylphenyl)-4hydroxyphenyl-C 13 -C 15 alkyl ester; IRGANOX 1520 (2,4-Bis[(octyl-thio)methyl]-o-cresol); IRGANOX 1010 (Pentaerythrittetrakis[3-(3,5-ditert-butyl-4-hydroxyphenyl)-propionate); IRGANOX 1076 (Octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionate]); and mixtures thereof.

2. The method of claim 1 , wherein said emulsion polymerization comprises polymerizing a styrene monomer and a butadiene monomer to form an emulsified styrene butadiene rubber.

3. The method of claim 1 , wherein the substituted phenol is capable of binding with a free radical and is added prior to or during the polymerization prior to the addition of a shortstopping agent.

4. The method of claim 1 , wherein the effective amount of a substituted phenol is from 0.01 to 5 parts per 100 parts monomer.

5. The method of claim 1 , wherein the polymerization results in a monomer conversion of greater than 85 weight percent.

6. The method of claim 1 , wherein the polymerization results in at least substantially gel-free emulsion polymer with less than 0.1% by weight gel.

7. The method of claim 1 , wherein the polymerization results in a polymer that is free of crosslinking.

8. The method of claim 1 , wherein the polymerization medium comprises a soap, water, modifier, and an activating agent.

9. The method of claim 1 , wherein the polymerization is conducted at a temperature of from 0 to 50° C.

10. The method of claim 1 , wherein the polymerization is conducted for from 4 to 20 hours.

11. The method of claim 1 , wherein the total monomer conversion is at least 5 percent higher based on total monomer conversion as compared to the same process conducted without adding a composition comprising an effective amount of a substituted phenol to the emulsion during the polymerization.

12. A process for making an emulsified rubber comprising:

(1) reacting styrene and butadiene in the presence of a soap, water, modifying agent, and an activating agent; and

(2) optionally terminating said reaction with a shortstopping agent; wherein an effective amount of a substituted phenol is added to the reaction mixture of step (1) to form an emulsified styrene-butadiene polymer having a low gel content and high monomer conversion and wherein the substituted phenol is selected from the group consisting of 2-6-di-t-butyl para-cresol; 2,6-bis(1,1-dimethylethyl)-4-methylphenol; octadecyl-3-(3,5-di-t-butyl-4-hydroxyphenyl)proprionate; benzenepropionic acid, 3,5-bis((1,1-dimethylphenyl)-4-hydroxyphenyl-C 13 -C 15 alkyl ester; IRGANOX 1520(2,4-Bis[(octyl-thio)methyl]-o-cresol); IRGANOX 1010 (Pentaerythrit-tetrakis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propionate]); IRGANOX 1076 (Octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionate); and mixtures thereof.

13. The process of claim 12 wherein the polymerization results in a monomer conversion of greater than 90 weight percent.

14. The process of claim 12 wherein the polymerization results in a monomer conversion of greater than 95 weight percent.

Assignments (10)
PATENT SECURITY AGREEMENT Recorded Sep 6, 2017
From: TRINSEO EUROPE GMBH
To: DEUTSCHE BANK AG NEW YORK BRANCH, AS COLLATERAL AGENT
Reel/Frame 043773/0138 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS RECORDED AT REEL 036303, FRAME 0749 Recorded Sep 6, 2017
From: DEUTSCHE BANK AG NEW YORK BRANCH
To: TRINSEO EUROPE GMBH
Reel/Frame 043773/0059 →
PATENT SECURITY AGREEMENT Recorded Aug 6, 2015
From: TRINSEO EUROPE GMBH
To: DEUTSCHE BANK AG NEW YORK BRANCH, AS COLLATERAL AGENT
Reel/Frame 036303/0749 →
CHANGE OF NAME Recorded Jun 25, 2015
From: STYRON EUROPE GMBH
To: TRINSEO EUROPE GMBH
Reel/Frame 036024/0806 →
CHANGE OF NAME Recorded Jun 12, 2015
From: STYRON EUROPE GMBH
To: TRINSEO EUROPE GMBH
Reel/Frame 036007/0670 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 12, 2011
From: STYRON LLC
To: STYRON EUROPE GMBH
Reel/Frame 026576/0053 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 12, 2011
From: EDEL, HANS; BARTOSSEK, HAGEN; MARX, DORIS R.
To: DOW OLEFINVERBUND GMBH
Reel/Frame 026576/0020 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 12, 2011
From: DOW OLEFINVERBUND GMBH
To: THE DOW CHEMICAL COMPANY
Reel/Frame 026576/0026 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 12, 2011
From: THE DOW CHEMICAL COMPANY
To: DOW GLOBAL TECHNOLOGIES INC.
Reel/Frame 026576/0030 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 12, 2011
From: DOW GLOBAL TECHNOLOGIES INC.
To: STYRON LLC
Reel/Frame 026576/0049 →
Continuity (2)
Provisional Application 61144633 · Jan 14, 2009
Related Publication 20110269930A1 · Nov 3, 2011