IP Library Granted Patent US 7,009,000
Granted Patent B2
US 7,009,000 · App. 10/618,394 · Granted Mar 7, 2006

Coupled styrenic block copolymers and process for preparing same

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Quick Facts
Patent No.
US 7,009,000
App. No.
10/618,394
Granted
Mar 7, 2006
Kind
B2
Abstract

Disclosed is an improvement to a process for preparing coupled styrenic block copolymers wherein adding from about 0.01 to about 1.5 equivalents of a metal alkyl compound per equivalent of living polymer chain ends to the cement, during or after polymerization, improves coupling efficiencies. The resultant radial styrenic block copolymers have reduced amounts of 5+ arm oligomers which can be very desirable is certain applications, such as the modification of bitumen.

Claims (42)

1. A method for preparing a radial styrenic block copolymer having a general formulas:

(AB) n X

wherein:

(i) A is a styrenic block,

(ii) B is a dienic block,

(iii) X is a residue of a diester coupling agent,

(iv) n is the number styrenic block copolymer arms bonded to the residue of a diester coupling agent,

(v) the molecular weight of the styreniec block copolymer arm (AB) is from about 2000 dalton to about 300,000 daltons, and

(vi) the weight percentage of the polymer wherein n is at least 5 is less than about 8 percent, comprising:

(a) contacting styrenic and dienic monomers with an anionic polymerization initiator which is an organo-substituted alkali metal compound in a suitable solvent to form a living polymer cement;

(b) adding from about 0.01 to about 1.5 equivalents of a metal alkyl compound per equivalent of living polymer chain ends to the cement, during or after polymerization, wherein the alkyl groups of the metal alkyl compound are chosen so that they will not exchange with the living polymer chain ends and the metal alkyl compound is selected from the group consisting of aluminum, zinc and magnesium alkyls having from 1 to 20 carbon atoms per alkyl substituent; and

(c) adding a diester coupling agent to the cement under reaction conditions sufficient to couple the living polymer; and

wherein the weight percentage of the polymer so formed having n=5 + is less than about 8 percent.

2. The method of claim 1 wherein 0.9:1 to 1.1:1 equivalents of a metal alkyl compound per equivalent of living polymer chain ends is added to the cement.

3. The method of claim 1 wherein the metal alkyl compound is a trialkyl aluminum compound.

4. The method of claim 3 wherein the trialkyl aluminum compound is triethyl aluminum.

5. The method of claim 1 wherein the molar ratio of diester to living polymer chains is from about 0.2:1 to about 0.3:1.

6. The method of claim 1 wherein the molar ratio of diester to living polymer chains is about 0.25:1.

7. The method of claim 1 wherein the metal alkyl compound is added in step (b) at or after 70 weight percent conversion of the monomers.

8. The method of claim 7 wherein the metal alkyl compound is added in step (b) at or after 90 weight conversion of the monomers.

9. A radial styrenic block copolymer having a general formula:

(AB) n X

wherein:

(i) A is a styrenic block,

(ii) B is a dienic block,

(iii) X is a residue of a diester coupling agent,

(iv) n is the number styrenic block copolymer arms bonded to the residue of a diester coupling agent,

(v) the molecular weight of the styrenic block copolymer arm (AB) is from about 2000 daltons to about 300,000 daltons, and

(vi) the weight percentage of the polymer wherein n=5 + is less than about 8 percent, and

wherein said copolymer is produced byte method of claim 1 .

10. The radial styrenic block copolymer of claim 9 wherein the weight percentage of the polymer wherein n=5 + is less than about 6 percent.

11. The radial styrenic block copolymer of claim 10 wherein the weight percentage of the polymer wherein n=5 + is less than about 5 percent.

12. The radial styrenic block copolymer of claim 9 wherein the weight percentage of the polymer wherein n=2 is less than about 5 percent.

13. The radial styrenic block copolymer of claim 12 wherein the weight percentage of the polymer wherein n=2 and n=5 + is less than about 12 percent.

14. The radial styrenic block copolymer of claim 9 wherein the styrenic block (A) is polystyrene.

15. The radial styrenic block copolymer of claim 9 wherein the dienic block (B) is selected from the group consisting of polybutadiene, polyisoprene and mixtures thereof.

16. The radial styrenic block copolymer of claim 9 wherein the molecular weight of the styrenic block copolymer arm (AB) is from about 3,000 daltons to about 150,000 daltons.

17. The radial styrenic block copolymer of claim 13 wherein the molecular weight of the styrenic block copolymer arm (AD) is from about 30,000 daltons to about 100,000 daltons.

18. The radial styrenic block copolymer of claim 9 wherein the residue of a diester coupling agent is a residue of a diester selected from the group consisting of dimethyl adipate, diethyl adipate, dimethyl terephthalate, diethyl terephthalate, and mixtures thereof.

19. A modified bitumen comprising an admixture of a radial styrenic block copolymer of claim 9 and bitumen.

20. A hydrogenated radial styrenic block copolymer prepared by hydrogenating a radial styrenic block copolymer of claim 9 .

21. The hydrogenated radial styrenic block copolymer of claim 20 , wherein the radial styrenic block copolymer of claim 9 is hydrogenated using a selective hydrogenation process.

Assignments (12)
CORRECTIVE ASSIGNMENT TO CORRECT THE PATENT NO. 8837224 TO PATENT NO. 7737224 PREVIOUSLY RECORDED AT REEL: 037448 FRAME: 0453. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Jun 11, 2022
From: KRATON POLYMERS U.S. LLC; ARIZONA CHEMICAL COMPANY, LLC
To: BANK OF AMERICA, N.A.
Reel/Frame 060344/0919 →
RELEASE OF SECURITY INTEREST Recorded Mar 16, 2022
From: BANK OF AMERICA, N.A.
To: KRATON POLYMERS U.S. LLC; KRATON CHEMICAL, LLC F/K/A ARIZONA CHEMICAL COMPANY, LLC; KRATON POLYMERS LLC; KRATON CORPORATION; KRATON CHEMICAL B.V.
Reel/Frame 059910/0017 →
RELEASE OF SECURITY INTEREST Recorded Mar 15, 2022
From: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS COLLATERAL AGENT
To: KRATON POLYMERS U.S. LLC
Reel/Frame 059366/0611 →
SECURITY INTEREST Recorded Apr 16, 2020
From: KRATON POLYMERS U.S. LLC; KRATON CHEMICAL, LLC F/K/A ARIZONA CHEMICAL COMPANY, LLC; KRATON POLYMERS LLC; KRATON CORPORATION
To: BANK OF AMERICA, N.A.
Reel/Frame 053020/0101 →
PATENT SECURITY AGREEMENT Recorded Jan 7, 2016
From: KRATON POLYMERS U.S. LLC
To: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS COLLATERAL AGENT
Reel/Frame 037457/0843 →
CORRECTIVE ASSIGNMENT TO CORRECT THE PATENT NUMBER 8837224 TO PATENT NUMBER 7737224 PREVIOUSLY RECORDED AT REEL: 037448 FRAME: 0453. ASSIGNOR(S) HEREBY CONFIRMS THE SECURITY INTEREST. Recorded Jan 6, 2016
From: KRATON POLYMERS U.S. LLC; ARIZONA CHEMICAL COMPANY, LLC
To: BANK OF AMERICA, N.A.
Reel/Frame 037448/0453 →
CORRECTIVE ASSIGNMENT TO CORRECT THE INCORRECT PATENT NUMBER 7720798 AND REPLACE WITH PATENT NUMBER 7220798 PREVIOUSLY RECORDED ON REEL 025845 FRAME 0795. ASSIGNOR(S) HEREBY CONFIRMS THE RELEASE BY SECURED PARTY. Recorded Dec 16, 2015
From: USB AG, STAMFORD BRANCH
To: KRATON POLYMERS U.S. LLC
Reel/Frame 037312/0070 →
RELEASE OF SECURITY INTEREST Recorded Mar 28, 2013
From: BANK OF AMERICA, N.A.
To: KRATON POLYMERS U.S. LLC
Reel/Frame 030108/0288 →
NOTICE OF GRANT OF SECURITY INTEREST IN PATENTS Recorded Mar 4, 2011
From: KRATON POLYMERS U.S. LLC
To: BANK OF AMERICA N.A., AS COLLATERAL AGENT
Reel/Frame 025899/0176 →
RELEASE OF SECURITY INTEREST Recorded Feb 24, 2011
From: UBS AG, STAMFORD BRANCH
To: KRATON POLYMERS U.S. LLC
Reel/Frame 025845/0795 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 7, 2005
From: BENING, ROBERT; ATWOOD, HARVEY; VAN DIJK, MARINUS P.; ROS, ADRIANA M. P.; MOORE, BARRY; WILLIS, CARL; VAN DIJK, NIKOLAAS J.
To: KRATON POLYMER U.S. LLC
Reel/Frame 017191/0055 →
SECURITY INTEREST Recorded Jan 2, 2004
From: KRATON POLYMERS U.S. LLC
To: UBS AG, STAMFORD BRANCH
Reel/Frame 014242/0281 →