# US 2019/0315899 A1 · Copolymer of 1,3,7-octatriene and isoprene, hydride thereof, and method for producing said copolymer

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- Number: US 2019/0315899 A1
- Document ID: US20190315899A1
- Status: Published application
- Kind: A1
- Application number: 16/472,510
- Filed: 2017-12-28
- Published: 2019-10-17
- Earliest claimed: 2016-12-28
- Assignees: Kuraray Co., Ltd.
- Applicants: Kuraray Co., Ltd.
- Inventors: Shuichi SUNAGA; Tomoaki TSUJI; Takashi HORI; Yasutaka INUBUSHI
- Web page: https://patentgrep.com/patent/US20190315899A1

## CPC

- C08F 236/22: the radical having three or more carbon-to-carbon double bonds
- C08F 2/38: Polymerisation using regulators, e.g. chain terminating agents {, e.g. telomerisation}
- C08F 8/04: Reduction, e.g. hydrogenation
- C08F 236/08: Isoprene
- C08F 2800/10: as molar percentages
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS

## Abstract

The present invention provides a copolymer of 1,3,7-octatriene and isoprene having a narrow molecular weight distribution (Mw/Mn) and a hydride thereof. Furthermore, in a production method of a copolymer containing a structural unit derived from 1,3,7-octatriene and a structural unit derived from isoprene, high raw material conversions are achieved for a short polymerization time. Specifically, the copolymer is a copolymer containing a structural unit derived from 1,3,7-octatriene and a structural unit derived from isoprene and is a copolymer having a molecular weight distribution (Mw/Mn) of less than 1.44, or the like.

## Claims

### Claim at position 1

1: A copolymer comprising a structural unit derived from 1,3,7-octatriene and a structural unit derived from isoprene, the copolymer having a molecular weight distribution (Mw/Mn) of less than 1.44.

### Claim at position 2

2: A copolymer comprising a structural unit derived from 1,3,7-octatriene and a structural unit derived from isoprene, the copolymer having a molecular weight distribution (Mw/Mn) smaller than a value determined according to the following formula (i):
3.1569×10−6×[Weight average molecular weight (Mw)]+1.1945 (i).

### Claim at position 3

3: A copolymer comprising a structural unit derived from 1,3,7-octatriene and a structural unit derived from isoprene, the copolymer having not only a content of the structural unit derived from 1,3,7-octatriene of more than 21.0 mol % relative to a total amount of the structural unit derived from 1,3,7-octatriene and the structural unit derived from isoprene, but also a molecular weight distribution (Mw/Mn) thereof of less than 2.06.

### Claim at position 4 (depends on 1)

4: The copolymer according to claim 1, having a weight average molecular weight (Mw) of 5,000 to 500,000.

### Claim at position 5 (depends on 1)

5: The copolymer according to claim 1, having a weight average molecular weight (Mw) of 20,000 to 500,000.

### Claim at position 6 (depends on 1)

6: The copolymer according to claim 1, having a weight average molecular weight (Mw) of 50,000 to 500,000.

### Claim at position 7 (depends on 1)

7: The copolymer according to claim 1, having a weight average molecular weight (Mw) of 210,000 to 500,000.

### Claim at position 8 (depends on 1)

8: The copolymer according to claim 1, not having a living anionic active species at a molecular end thereof.

### Claim at position 9 (depends on 1)

9: The copolymer according to claim 1, having a living anionic active species at a molecular end thereof.

### Claim at position 10

10: A copolymer comprising a structural unit derived from 1,3,7-octatriene and a structural unit derived from isoprene, the copolymer having a living anionic active species at a molecular end thereof and having a molecular weight distribution (Mw/Mn) of 2.50 or less.

### Claim at position 11 (depends on 10)

11: The copolymer according to claim 10, having a weight average molecular weight (Mw) of 5,000 to 500,000.

### Claim at position 12 (depends on 1)

12: The copolymer according to claim 1, further comprising a structural unit derived from a conjugated diene compound having 6 or more carbon atoms.

### Claim at position 13 (depends on 12)

13: The copolymer according to claim 12, wherein the conjugated diene compound having 6 or more carbon atoms is at least one selected from the group consisting of 2,3-dimethyl-1,3-butadiene, 4,5-diethyl-1,3-butadiene, 2-phenyl-1,3-butadiene, 2-hexyl-1,3-butadiene, 2-benzyl-1,3-butadiene, 2-p-toluyl-1,3-butadiene, 2-methyl-1,3-pentadiene, 3-methyl-1,3-pentadiene, 2,3-dimethyl-1,3-pentadiene, 2,3-diethyl-1,3-pentadiene, 1,3-hexadiene, 2,3-dimethyl-1,3-hexadiene, 2,3-diethyl-1,3-heptadiene, 3-butyl-1,3-octadiene, 2,3-dimethyl-1,3-octadiene, 4,5-diethyl-1,3-octadiene, 1,3-cyclohexadiene, and myrcene.

### Claim at position 14 (depends on 1)

14: A hydride of the copolymer according to claim 1.

### Claim at position 15

15: A method of producing a copolymer containing a structural unit derived from 1,3,7-octatriene and a structural unit derived from isoprene, the method comprising subjecting 1,3,7-octatriene having a purity, as determined by gas chromatography, of more than 98.0% and isoprene to anionic polymerization, wherein
impurities which may be contained in the 1,3,7-octatriene include at least one selected from the group consisting of a peroxide and its decomposition product, and a total content of the peroxide and its decomposition product in the 1,3,7-octatriene is 0.30 mmol/kg or less; and
the copolymer satisfies at least one of the following conditions I to III:
Condition I: a molecular weight distribution (Mw/Mn) is less than 1.44;
Condition II: a molecular weight distribution (Mw/Mn) is smaller than a value determined according to the following formula (i):
3.1569×10−6×[Weight average molecular weight (Mw)]+1.1945 (i); and
Condition III: not only a content of the structural unit derived from 1,3,7-octatriene is more than 21.0 mol % relative to a total amount of the structural unit derived from 1,3,7-octatriene and the structural unit derived from isoprene, but also a molecular weight distribution (Mw/Mn) thereof is less than 2.06.

### Claim at position 16 (depends on 15)

16: The method of claim 15, wherein the 1,3,7-octatriene has a purity, as determined by gas chromatography, of 98.5% or more.

### Claim at position 17 (depends on 15)

17: The method of claim 15, wherein the anionic polymerization is carried out in the presence of a Lewis base.

### Claim at position 18 (depends on 17)

18: The method of claim 17, wherein a molar ratio of the Lewis base to a polymerization initiator used for the anionic polymerization [(Lewis base)/(polymerization initiator)] is from 0.01 to 1,000.

### Claim at position 19 (depends on 17)

19: The method of claim 17, wherein the Lewis base is a compound having at least one selected from the group consisting of an ether bond and a tertiary amino group in a molecule thereof.

### Claim at position 20 (depends on 17)

20: The method of claim 17, wherein the Lewis base is a compound having one atom having an unshared electron pair.

### Claim at position 21 (depends on 17)

21: The method of claim 17, wherein the Lewis base is a compound having two or more atoms having an unshared electron pair.

### Claim at position 22 (depends on 21)

22: The method of claim 21, wherein the Lewis base has multidentate properties.

### Claim at position 23 (depends on 15)

23: The method of claim 15, wherein a solid content concentration of a reaction liquid obtained after completion of the anionic polymerization is from 10 to 80% by mass.

### Claim at position 24 (depends on 15)

24: The method of claim 15, wherein the anionic polymerization is carried out at −50 to 200° C.

### Claim at position 25 (depends on 15)

25: The method of claim 15, wherein a conversion of the 1,3,7-octatriene after completion of the anionic polymerization, as determined by gas chromatography, is 80.0% or more.

### Claim at position 26 (depends on 15)

26: The method of claim 15, wherein a conversion of the 1,3,7-octatriene after completion of the anionic polymerization, as determined by gas chromatography, is 88.0% or more.