IP Library Granted Patent US 11,976,190
Granted Patent B2
US 11,976,190 · App. 17/040,829 · Granted May 7, 2024

Block copolymer, method for producing same, rubber composition using said block copolymer, and tire

Inventor: Daisuke Koda (Kamisu, JP)
Assignees: KURARAY CO., LTD.; AMYRIS, INC.
C08L53/02B60C1/00C08F212/08C08F236/06C08F236/22C08K3/04C08K3/36C08K5/5419C08F2438/00
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Quick Facts
Patent No.
US 11,976,190
App. No.
17/040,829
Granted
May 7, 2024
Kind
B2
Abstract

The present invention relates to a block copolymer that contains a polymer block A containing a farnesene-derived monomer unit (a1) and a random copolymer block B containing a C12 or lower conjugated diene-derived monomer unit (b1) and an aromatic vinyl compound-derived monomer unit (b2), the block copolymer having a ratio by mass of the polymer block A to the random copolymer block B (A/B) of 30/70 to 0.5/99.5, a content of the aromatic vinyl compound-derived monomer unit (b2) in the random copolymer block B of 1 to 50% by mass, and a weight average molecular weight (Mw) of 100,000 to 5,000,000.

Claims (45)

1. A block copolymer, comprising:

a polymer block A comprising a farnesene-derived monomer unit (a1); and

a random copolymer block comprising a C12 or lower conjugated diene-derived monomer unit (b1) and an aromatic vinyl compound-derived monomer unit (b2),

wherein the block copolymer has an A/B mass ratio of the polymer block A to the random copolymer block B in a range of from 30170 to 0.5/99.5,

wherein the block copolymer has a content of the aromatic vinyl compound-derived monomer unit (b2) in the random copolymer block B in a range of from 1 to 50% by mass,

wherein the block copolymer has a weight average molecular weight as determined by gel permeation chromatography based on polystyrene in a range of from 100,000 to 5,000,000,

wherein at least a part of the block copolymer is a block copolymer in which terminals of linear block copolymer chains are bonded to one another via a coupling agent, and

wherein the coupling ratio is 40% by mass or less.

2. The block copolymer of claim 1 , having a content of the farnesene-derived monomer unit (a1) in the polymer block A of 60% by mass or more.

3. The block copolymer of claim 1 , having a total content of the C12 or lower conjugated diene-derived monomer unit (b1) and the aromatic vinyl compound-derived monomer unit (b2) in the random copolymer block B of 60% by mass or more.

4. The block copolymer of claim 1 , wherein

the coupling ratio is in a range of from 1 to 40% by mass.

5. The block copolymer of claim 1 , wherein at least a part of the block copolymer is a branched block copolymer in which terminals of linear block copolymer chains are bonded to one another via a coupling agent.

6. The block copolymer of claim 1 , wherein the block copolymer has the polymer block A at a terminus of a molecular chain of the block copolymer.

7. A method for producing a block copolymer, the method comprising:

polymerizing a monomer comprising farnesene in the presence of an organic metal initiator to produce a living polymer comprising the polymer block A; and

polymerizing monomers comprising a C12 or lower conjugated diene and an aromatic vinyl compound in the presence of the living polymer comprising the polymer block A to produce a living block copolymer comprising the polymer block A and a random copolymer block B,

wherein the block copolymer comprises a polymer block A comprising a farnesene-derived monomer unit (a1) and the random copolymer block B comprising a C12 or lower conjugated diene-derived monomer unit (b1) and an aromatic vinyl compound-derived monomer unit (b2),

wherein at least a part of the block copolymer is a block copolymer in which terminals of linear block copolymer chains are bonded to one another via a coupling agent, and

wherein the coupling ratio is 40% by mass or less.

8. The method of claim 7 , further comprising:

coupling at least a part of the living block copolymer comprising the polymer block A and the random copolymer block B with a coupling, agent.

9. A method for producing a block copolymer, the method comprising:

polymerizing monomers comprising a C12 or lower conjugated diene and an aromatic vinyl compound in the presence am organic metal initiator to produce a living polymer comprising a random copolymer block B; and

polymerizing a monomer comprising farnesene in the presence of the living polymer comprising the random copolymer block B to produce a living block copolymer comprising a polymer block A and the random copolymer block B,

wherein the block copolymer comprises the polymer block A comprising a farnesene-derived monomer unit (a1) and the random copolymer block B comprising a C12 or lower conjugated diene-derived monomer unit (b1) and an aromatic vinyl compound-derived monomer unit (b2),

wherein at least a part of the block copolymer is a block copolymer in which terminals of linear block copolymer chains are bonded to one another via a coupling agent, and

wherein the coupling, ratio is 40% by mass or less.

10. The method of claim 9 , further comprising:

coupling at least a part of the living block copolymer comprising the polymer block A and the random copolymer block B with a coupling agent.

11. A rubber composition, comprising:

a rubber component (I) comprising the block copolymer of claim 1 ; and

a filler (II),

wherein the rubber composition has a content of the block copolymer in the total amount of the rubber component (I) in a range of from 0.1 to 99.9% by mass, and

wherein the rubber composition comprises the filler (II) in an amount in a range of from 20 to 150 parts by mass, relative to 100 parts by mass of the rubber component (I).

12. A tire, comprising,

the rubber composition of claim 11 .

13. The block copolymer of claim 1 , wherein the coupling ratio is in a range of from 1 to 30% by mass.

14. The block copolymer of claim 1 , wherein the coupling ratio is in a range of from 5 to 28% by mass.

15. The block copolymer of claim 1 , wherein the coup mg ratio is in a range of from 10 to 25% by mass.

16. The block copolymer of claim 1 , wherein the A/B mass ratio of the block copolymer is in a range of from 23/73 to 0.7/99.3.

17. The block copolymer of claim 1 , having a glass transition temperature in a range of from −90 to −10° C.

18. The block copolymer of claim 1 , having a total content of the C12 or lower conjugated diene-derived monomer unit (b1) and the aromatic vinyl compound-derived monomer unit (b2) in the random copolymer block B in a range of from 80 to 100% by mass.

19. The block copolymer of claim 1 , having a total content of the C12 or lower conjugated diene-derived monomer unit (b1) and the aromatic vinyl compound-derived monomer unit (b2) in the random copolymer block B in a range of from 90 to 100% by mass.

20. The block copolymer of claim 1 , having a total content of the C12 lower conjugated diene-derived monomer unit (b1) and the aromatic vinyl compound-derived monomer unit (b2) in the random copolymer block B in a range of from 98 to 100% by mass.

Assignments (6)
SECURITY INTEREST Recorded Dec 5, 2024
From: AMYRIS, INC.
To: EUAGORE, LLC
Reel/Frame 069502/0957 →
SECURITY INTEREST Recorded May 24, 2024
From: AMYRIS, INC.
To: EUAGORE, LLC
Reel/Frame 067528/0467 →
SECURITY INTEREST Recorded Aug 17, 2023
From: AMYRIS, INC.; AMYRIS CLEAN BEAUTY, INC.; AMYRIS FUELS, LLC; AB TECHNOLOGIES LLC; APRINNOVA, LLC; AMYRIS-OLINKA, LLC; ONDA BEAUTY INC.; UPLAND 1 LLC; AMYRIS ECO-FAB LLC; CLEAN BEAUTY 4U HOLDINGS, LLC; AMYRIS CLEAN BEAUTY LATAM LTDA; INTERFACES INDUSTRIA E COMERCIA DE COSMETICOS LTDA; AMYRIS BIOTECHNOLOGIA DO BRASIL LTDA; AMYRIS EUROPE TRADING B.V. (NETHERLANDS); AMYRIS BIO PRODCUTS PORTUGAL, UNIPESSOAL, LDA; BEAUTY LABS INTERNATIONAL LIMITED; AMYRIS UK TRADING LIMITED
To: EUAGORE, LLC
Reel/Frame 064619/0778 →
SECURITY INTEREST Recorded Aug 3, 2023
From: AMYRIS CLEAN BEAUTY, INC.; AMYRIS FUELS, LLC; AB TECHNOLOGIES LLC; AMYRIS, INC.
To: MUIRISC, LLC
Reel/Frame 064492/0518 →
SECURITY INTEREST Recorded Oct 18, 2022
From: AMYRIS, INC.
To: FORIS VENTURES, LLC
Reel/Frame 061703/0499 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 23, 2020
From: KODA, DAISUKE
To: KURARAY CO., LTD.; AMYRIS, INC.
Reel/Frame 053861/0514 →
Priority Claims (1)
JP 2018-066034 · Mar 29, 2018 · national
Continuity (1)
Related Publication 20210017378A1 · Jan 21, 2021