IP Library Granted Patent US 9,000,109
Granted Patent B2
US 9,000,109 · App. 14/001,612 · Granted Apr 7, 2015

High styrene high vinyl styrene-butadiene rubber and methods for preparation thereof

Inventors: Evemarie Hamann (Halle, DE); Silvia Valenti (Halle, DE); Karin Schmiedel (Halle, DE)
Assignee: Styron Europe GmbH
C08F236/10C08F212/08C08L9/06
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Quick Facts
Patent No.
US 9,000,109
App. No.
14/001,612
Granted
Apr 7, 2015
Kind
B2
Abstract

A process for polymerization of a polymer containing monomeric units derived from a styrene monomer and a 1,3-butadiene monomer includes polymerizing the monomeric units in the presence of an initiator, a first polar agent, and a second polar agent. The first polar agent includes a structure (I): R 1′ R 2′ N-Q-NR 3′ R 4′ ; and the second polar agent comprises a structure (II): R 1′ , R 2 ′, R 3′ , and R 4′ are each independently selected from the group consisting of an alkyl group and hydrogen; Q contains an alkylene group; R 1 and R 2 are each independently an alkyl group; and R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are each independently selected from the group consisting of an alkyl group and hydrogen. Polymers prepared by the above process are described, as are compositions containing such a polymer, and articles containing at least one component formed from such a composition.

Claims (26)

1. A process for polymerization of a polymer comprising monomeric units derived from a styrene monomer and a 1,3-butadiene monomer, the process comprising:

polymerizing the monomers in the presence of an initiator, a first polar agent, and a second polar agent;

wherein the first polar agent comprises a structure (I):

R 1′ R 2′ N-Q-NR 3′ R 4′   (I);

wherein the second polar agent comprises a structure (II):

wherein R 1′ , R 2′ , R 3′ , and R 4′ are each independently selected from the group consisting of an alkyl group and hydrogen;

wherein Q comprises an alkylene group;

wherein R 1 and R 2 are each independently an alkyl group;

wherein R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are each independently selected from the group consisting of an alkyl group and hydrogen; and wherein the polymer comprises a vinyl content from greater than 30 to about 80 weight percent, based on toatle amount of polymerized 1, 3-butadiene.

2. The process as in claim 1 wherein R 1′ , R 2′ , R 3′ , and R 4′ are each independently selected from the group consisting of hydrogen and a C 1 -C 4 alkyl group.

3. The process of claim 1 wherein the alkylene group comprises a structure —(CH 2 ) n —, wherein n is an integer equal to or greater than 2.

4. The process of claim 1 wherein R 1 and R 2 are each independently a C 1 -C 4 alkyl group.

5. The process of claim 1 wherein R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are each independently selected from the group consisting of hydrogen and a C i -C 4 alkyl group.

6. The process of claim 1 wherein a molar ratio of the second polar agent to the first polar agent is between about 0.01 and about 10.

7. The process of claim 1 wherein the first polar agent comprises tetramethylethylenediamine.

8. The process of claim 1 wherein the second polar agent comprises ditetrahydrofurylpropane.

9. The process of claim 1 wherein the polymer comprises a styrene content from about 20 to about 80 weight percent.

10. The process of claim 1 wherein the polymer has a molecular weight distribution from about 1.05 to about 1.8.

11. The process of claim 1 wherein the polymer has a number-average molecular weight greater than or equal to about 100,000 g/mole.

12. The process of claim 1 wherein the polymer has a weight-average molecular weight greater than or equal to about 180,000 g/mole.

13. The process of claim 1 wherein the polymer has only one glass transition temperature (Tg), which is about −50° C. to about 20° C.

14. The process of claim 1 wherein a molar ratio of the first polar agent to active initiator is greater than about 0.3.

15. The process of claim 1 wherein a molar ratio of the second polar agent to active initiator is greater than about 0.3.

16. The process of claim 1 wherein the polymerization is run at a temperature of between about 10° C. and about 80° C.

17. The process of claim 1 wherein the initiator comprises n-butyl lithium.

18. The process of claim 1 wherein the polymerizing takes place in a hydrocarbon solvent.

Assignments (6)
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 Sep 6, 2017
From: TRINSEO EUROPE GMBH
To: DEUTSCHE BANK AG NEW YORK BRANCH, AS COLLATERAL AGENT
Reel/Frame 043773/0138 →
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 May 12, 2014
From: HAMANN, EVEMARIE; VALENTI, SILVIA; SCHMIEDEL, KARIN
To: STYRON EUROPE GMBH
Reel/Frame 032869/0090 →
Priority Claims (1)
EP 11156988 · Mar 4, 2011 · regional
Continuity (1)
Related Publication 20130345379A1 · Dec 26, 2013