IP Library › Granted Patent US 9,315,608
Granted Patent B2
US 9,315,608 · App. 14/219,540 · Granted Apr 19, 2016

Conjugated diene polymer rubber, and conjugated diene polymer rubber composition

Inventors: Toru Fujii (Singapore, SG); Takuya Sudo (Chiba, JP); Mayumi Oshima (Tokyo, JP); Katsunari Inagaki (Chiba, JP)
Assignee: SUMITOMO CHEMICAL COMPANY, LIMITED
C08F279/02C08C19/44C08F236/04C08L15/00C08L19/006C08K3/36C08K5/548
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Quick Facts
Patent No.
US 9,315,608
App. No.
14/219,540
Granted
Apr 19, 2016
Kind
B2
Abstract

A conjugated diene polymer rubber is provided that includes component (A) and component (B) below, component (A) having a content, with the total amount of component (A) and component (B) as 100% by weight, of from 5% to 90% by weight, and component (B) having a content of from 95% to 10% by weight, Component (A): a conjugated diene polymer rubber component modified with a carbonyl group- and substituted amino group-containing compound Component (B): a conjugated diene polymer rubber component modified with a compound represented by formula (IIa) below (R 21 O) m Si(R 22 A) n R 23 4-m-n   (IIa) wherein m denotes a number from 1 to 3, n denotes a number from 1 to 3, m+n is from 2 to 4, R 21 and R 23 denote a hydrocarbyl group, R 22 denotes a hydrocarbylene group, A denotes a substituted amino group or an optionally substituted hydrocarbyloxy group, when there are a plurality of R 21 s the plurality of R 21 s may be identical to or different from each other, when there are a plurality of R 22 s the plurality of R 22 s may be identical to or different from each other, when there are a plurality of R 23 s the plurality of R 23 s may be identical to or different from each other, and when there are a plurality of As the plurality of As may be identical to or different from each other.

Claims (22)

1. A method for producing a conjugated diene polymer rubber,

the conjugated diene polymer rubber comprising component (A) and component (B) below, the component (A) having a content, with the total amount of the component (A) and the component (B) as 100% by weight, of from 5 to 90% by weight, and the component (B) having a content of from 95 to 10% by weight,

wherein the component (A) is produced by a process comprising steps A and B:

step A: copolymerizing a monomer component including a conjugated diene and a vinyl monomer represented by formula (X) below in a hydrocarbon solvent in the presence of an alkali metal catalyst,

wherein X 1 , X 2 , and X 3 denote an optionally substituted hydrocarbyl group or a group represented by formula (Xa) below, and at least one of X 1 , X 2 , and X 3 is a group represented by formula (Xa) below,

wherein R′ and R″ denote a hydrocarbyl group having 1 to 6 carbon atoms that may contain at least one atom selected from the group consisting of a nitrogen atom, an oxygen atom, and a silicon atom, a silyl group, a substituted silyl group, or a divalent group having 2 to 12 carbon atoms in which R′ and R″ are bonded to each other, and * represents a bonding position, and

step B: reacting the resulting polymer in step A with a carbonyl group- and substituted amino group-containing compound, and

wherein the component (B) is produced by a process comprising steps C and D:

step C: copolymerizing a monomer component including a conjugated diene and a vinyl monomer represented by formula (X) above in a hydrocarbon solvent in the presence of an alkali metal catalyst, and

step D: reacting the resulting polymer in step C with a compound represented by formula (IIa) below,

(R 21 O) m Si(R 22 A) n R 23 4-m-n   (IIa)

wherein m denotes a number from 1 to 3, n denotes a number from 1 to 3, m+n is from 2 to 4, R 21 and R 23 denote a hydrocarbyl group, R 22 denotes a hydrocarbylene group, A denotes a substituted amino group or an optionally substituted hydrocarbyloxy group, when there are a plurality of R 21 s the plurality of R 21 s may be identical to or different from each other, when there are a plurality of R 22 s the plurality of R 22 s may be identical to or different from each other, when there are a plurality of R 23 s the plurality of R 23 s may be identical to or different from each other, and when there are a plurality of As the plurality of As may be identical to or different from each other.

2. The method according to claim 1 , wherein the carbonyl group- and substituted amino group-containing compound is a compound represented by formula (Ia) below,

wherein Z 1 and Z 2 denote a substituted amino group-containing group, a hydrogen atom, an optionally substituted hydrocarbyl group, or an optionally substituted hydrocarbyloxy group, at least one of Z 1 and Z 2 is a substituted amino group-containing group, or Z 1 and Z 2 are bonded to each other and denote a group in which a substituted amino group-containing ring structure is formed by Z 1 , Z 2 , and the carbonyl carbon.

3. The method according to claim 2 , wherein at least one of Z 1 and Z 2 of formula (Ia) is a group represented by formula (Ib) below,

wherein p denotes 0 or 1, T denotes an oxygen atom or —NR 6 —, R 6 denotes a hydrocarbyl group or a hydrogen atom, R 4 denotes a hydrocarbylene group, R 5 denotes a hydrocarbyl group that may contain a nitrogen atom and/or an oxygen atom, the two R 5 s may be identical to or different from each other, a group having 2 to 20 carbon atoms in which the two R 6 s form a single group and are bonded to the nitrogen atom via a double bond, or a divalent group having 2 to 20 carbon atoms in which the two R 5 s are bonded to each other, and * represents a bonding position.

4. The method according to claim 1 , wherein the carbonyl group- and substituted amino group-containing compound is a compound represented by formula (1-3) below,

wherein R 5 denotes a hydrocarbyl group that may contain a nitrogen atom and/or an oxygen atom, the two R 5 s may be identical to or different from each other, a group having 2 to 20 carbon atoms in which the two R 5 s form a single group and are bonded to the nitrogen atom via a double bond, or a divalent group having 2 to 20 carbon atoms in which the two R 5 s are bonded to each other, q denotes an integer from 1 to 10, T denotes an oxygen atom or —NR 6 —, R 6 denotes a hydrocarbyl group or a hydrogen atom, and R 8 denotes an optionally substituted hydrocarbyl group or a hydrogen atom.

5. The method according to claim 1 , wherein the compound represented by formula (IIa) is a [3-(dialkylamino)propyl]trialkoxysilane.

6. The method according to claim 1 , wherein the conjugated diene polymer rubber has a vinyl bond content, with the conjugated diene-based constituent unit content as 100% by mole, of not less than 20% by mole and not more than 70% by mole.

7. A method for producing a conjugated diene polymer rubber composition,

the method comprising a step of mixing 100 parts by weight of the conjugated diene polymer rubber producing by the method according to claim 1 , and 10 to 150 parts by weight of a filler.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 12, 2025
From: SUMITOMO CHEMICAL COMPANY, LIMITED
To: ZEON CORPORATION
Reel/Frame 070481/0713 →
Priority Claims (2)
JP 2010-041901 · Feb 26, 2010 · national
JP 2010-041902 · Feb 26, 2010 · national
Continuity (2)
Division 13034067 · Feb 24, 2011
Related Publication 20140206811A1 · Jul 24, 2014