# US 10,246,525 B2 · Process for producing conjugated diene polymer

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- Number: US 10,246,525 B2
- Document ID: US10246525B2
- Status: Granted
- Kind: B2
- Application number: 15/506,495
- Filed: 2015-09-07
- Published: 2017-09-14
- Granted: 2019-04-02
- Earliest claimed: 2014-09-09
- Assignees: Asahi Kasei Kabushiki Kaisha
- Applicants: Asahi Kasei Kabushiki Kaisha
- Inventors: Tetsuji Tokiwa
- Web page: https://patentgrep.com/patent/US10246525B2

## CPC

- C08C 2/02: Purification
- B29B 7/48: with intermeshing devices, e.g. screws
- B29B 13/00: Conditioning or physical treatment of the material to be shaped (chemical aspects C08J3/00 {; heating, cooling or curing during shaping B29C35/00; thermal after-treatment B29C71/02})
- B29B 13/06: by drying (B29B13/08 takes precedence {; drying moulded articles or half products B29C37/0092})
- C08C 19/22: Incorporating nitrogen atoms into the molecule
- C08C 19/25: Incorporating silicon atoms into the molecule
- C08F 6/10: Removal of volatile materials, e.g. solvents {(C08F6/001, C08F6/003, C08F6/005, C08F6/006, C08F6/008, C08F6/02, C08F6/04 take precedence)}
- C08F 8/00: Chemical modification by after-treatment (graft polymers, block polymers, crosslinking with unsaturated monomers or with polymers C08F251/00 - C08F299/00; of conjugated diene rubbers C08C)
- C08F 36/00: Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds (C08F32/00 takes precedence)
- C08J 3/005: {Processes for mixing polymers}
- B29B 2013/002: {Extracting undesirable residual components, e.g. solvents, unreacted monomers, from material to be moulded}
- B29K 2009/00: Use of rubber derived from conjugated dienes, as moulding material
- C08F 8/42: Introducing metal atoms or metal-containing groups
- C08J 2309/06: Copolymers with styrene
- C08C: TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- B29B: PREPARATION OR PRETREATMENT OF THE MATERIAL TO BE SHAPED; MAKING GRANULES OR PREFORMS; RECOVERY OF PLASTICS OR OTHER CONSTITUENTS OF WASTE MATERIAL CONTAINING PLASTICS
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)
- B29K: INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR {MOULDS, } REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS

## Abstract

The present invention provides a process for producing a conjugated diene polymer, the process including a production step of producing a conjugated diene polymer solution containing a conjugated diene polymer and a solvent, and a devolatilization step of heating the conjugated diene polymer solution while conveying the conjugated diene polymer solution with an apparatus having rotary twin screws, thereby devolatilizing the solvent, in which a motor current value of the screw in the devolatilization step and a motor current value of the screw under no load satisfy a predetermined relational expression.

## Claims

### Claim 1

A process for producing a conjugated diene polymer, the process comprising:
a production step of producing a conjugated diene polymer solution comprising a conjugated diene polymer and a solvent; and
a devolatilization step of heating the conjugated diene polymer solution while conveying the conjugated diene polymer solution with an apparatus comprising rotary twin screws, thereby devolatilizing the solvent,
wherein a motor current value of the screw in the devolatilization step and a motor current value of the screw under no load satisfy following relational expression (1):
1.05≤((I1)/(I0))≤2.00 (1)
wherein I1 represents the motor current value [A] of the screw in the devolatilization step and I0 represents the motor current value [A] of the screw under no load,
wherein:
a ratio of a screw length to a screw diameter in the apparatus is 4.0 or more and 12 or less; and,
in the devolatilization step, an inner volume of the apparatus and an amount of the solvent volatilizing per unit time satisfy following relational expression (2):
1.0≤((VA)/(V0))≤50 (2)
wherein (V0) represents the inner volume [L] of the apparatus and (VA) represents the amount [L] of the solvent volatilizing per unit time [h].

### Claim 2 (depends on 1)

The process for producing the conjugated diene polymer according to claim 1, wherein the conjugated diene polymer has a weight average molecular weight of 100,000 or higher and 2,000,000 or lower.

### Claim 3 (depends on 1)

The process for producing the conjugated diene polymer according to claim 1, wherein the conjugated diene polymer solution comprises 5.0% by mass or more and 95% by mass or less of the conjugated diene polymer based on the total amount of the conjugated diene polymer solution.

### Claim 4 (depends on 1)

The process for producing the conjugated diene polymer according to claim 1, wherein the conjugated diene polymer solution comprises 5.0 parts by mass or more and 100 parts by mass or less of oil based on 100 parts by mass of the conjugated diene polymer.

### Claim 5 (depends on 1)

The process for producing the conjugated diene polymer according to claim 1, wherein two or more of apparatuses each comprising twin screws are used in the devolatilization step.

### Claim 6 (depends on 1)

The process for producing the conjugated diene polymer according to claim 1, wherein the conjugated diene polymer comprises 1.0% by mass or more and 99% by mass or less of a component having a molecular weight of 1000000 or higher based on the total amount of the conjugated diene polymer.

### Claim 7 (depends on 1)

The process for producing the conjugated diene polymer according to claim 1, wherein an average residence time in the devolatilization step is 10 seconds or longer and 300 seconds or shorter.

### Claim 8 (depends on 1)

The process for producing the conjugated diene polymer according to claim 1, wherein the devolatilization step is a step of devolatilizing the solvent until the content of the solvent reaches 5.0% by mass or less based on the total amount of the conjugated diene polymer obtained.

### Claim 9 (depends on 1)

The process for producing the conjugated diene polymer according claim 1, wherein the conjugated diene polymer is modified with a compound having at least one functional group selected from the group consisting of epoxy groups and alkoxysilyl groups.

### Claim 10 (depends on 9)

The process for producing the conjugated diene polymer according to claim 9, wherein the compound is at least one compound selected from the group consisting of compounds represented by following general formula (3) and compounds represented by following general formula (4):
wherein R1 and R2 each independently represent an alkyl group having 1 to 10 carbon atoms or an alkyl group having 1 to 10 carbon atoms and having at least one functional group selected from the group consisting of ether groups and tertiary amine groups, R3 and R4 each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or an alkyl group having 1 to 20 carbon atoms and having at least one functional group selected from the group consisting of ether groups and tertiary amine groups, R5 represents an alkyl group having 1 to 20 carbon atoms or an alky group having 1 to 20 carbon atoms and having at least one functional group selected from the group consisting of ether groups, tertiary amine groups, epoxy groups, carbonyl groups and halogens, and n represents an integer of 1 to 6; and
wherein R1 and R2 each independently represent an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 20 carbon atoms, R3 and R4 each independently represent an alkyl group having 1 to 20 carbon atoms, R5 represents an alkyl group having 1 to 6 carbon atoms and forms a five or more-membered cyclic structure with an adjacent nitrogen atom and an adjacent silicon atom, R6 represents an alkyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, not having an active hydrogen atom, and substituted with a heteroatom, or an organosubstituted silyl group, m represents an integer of 1 or 2, and n represents an integer of 2 or 3.

### Claim 11 (depends on 1)

The process for producing the conjugated diene polymer according to claim 1, wherein
the conjugated diene polymer has a weight average molecular weight of 100,000 or higher and 2,000,000 or lower,
the conjugated diene polymer solution comprises 5.0% by mass or more and 95% by mass or less of the conjugated diene polymer based on the total amount of the conjugated diene polymer solution,
the conjugated diene polymer solution comprises 5.0 parts by mass or more and 100 parts by mass or less of oil based on 100 parts by mass of the conjugated diene polymer,
two or more of apparatuses each comprising twin screws are used in the devolatilization step,
the conjugated diene polymer comprises 1.0% by mass or more and 99% by mass or less of a component having a molecular weight of 1000000 or higher based on the total amount of the conjugated diene polymer,
an average residence time in the devolatilization step is 10 seconds or longer and 300 seconds or shorter,
the devolatilization step is a step of devolatilizing the solvent until the content of the solvent reaches 5.0% by mass or less based on the total amount of the conjugated diene polymer obtained, and
the conjugated diene polymer is modified with a compound having at least one functional group selected from the group consisting of epoxy groups and alkoxysilyl groups.

### Claim 12 (depends on 2)

The process for producing the conjugated diene polymer according to claim 2, wherein the conjugated diene polymer solution comprises 5.0 parts by mass or more and 100 parts by mass or less of oil based on 100 parts by mass of the conjugated diene polymer.

### Claim 13 (depends on 2)

The process for producing the conjugated diene polymer according to claim 2, wherein two or more of apparatuses each comprising twin screws are used in the devolatilization step.

### Claim 14 (depends on 3)

The process for producing the conjugated diene polymer according to claim 3, wherein two or more of apparatuses each comprising twin screws are used in the devolatilization step.