# US 10,118,974 B2 · Modified conjugated diene polymer, a modified rubber composition containing same, and method for preparing modified conjugated diene polymer

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- Number: US 10,118,974 B2
- Document ID: US10118974B2
- Status: Granted
- Kind: B2
- Application number: 15/121,804
- Filed: 2015-11-03
- Published: 2017-01-26
- Granted: 2018-11-06
- Earliest claimed: 2014-12-11
- Assignees: LG Chem, Ltd.
- Applicants: LG Chem, Ltd.
- Inventors: Hae-Sung Sohn; No-Ma Kim; He-Seung Lee
- Web page: https://patentgrep.com/patent/US10118974B2

## CPC

- C08C 19/44: of polymers containing metal atoms exclusively at one or both ends of the skeleton
- B60C 1/0016: {Compositions of the tread}
- C07F 7/1804: {Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896)}
- C08C 19/22: Incorporating nitrogen atoms into the molecule
- C08C 19/25: Incorporating silicon atoms into the molecule
- C08C 19/26: Incorporating metal atoms into the molecule
- C08F 36/04: conjugated
- C08K 3/36: Silica
- C08L 15/00: Compositions of rubber derivatives (C08L11/00, C08L13/00 take precedence)
- Y02T 10/86: Optimisation of rolling resistance, e.g. weight reduction
- C08C: TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- B60C: VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- Y02T: CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO TRANSPORTATION

## Abstract

Disclosed are a modified conjugated diene-based polymer represented by a specific Chemical Formula and a method of preparing the same.

## Claims

### Claim 1

A modified conjugated diene-based polymer, which is a compound represented by Chemical Formula 2 below:
wherein R2 is
or a C1-C50 alkyl group, Pn and Pm are polymers comprising a conjugated diene monomer and a conjugated aromatic monomer as main components, with a number average molecular weight of 1,000 to 10,000,000 g/mol, and including an acryl, amine, ether or thioether monomer, Pn and Pm are identical to or different from each other, a is 1 to 3, b is 0 to 3, n is 1 to 20, and m is 0 to 20.

### Claim 2 (depends on 1)

The modified conjugated diene-based polymer of claim 1, wherein the compound represented by Chemical Formula 2 is a compound represented by Chemical Formula 2a below:
wherein a1 to a8 each range from 10 to 100,000.

### Claim 3

A method of preparing a modified conjugated diene-based polymer, comprising:
a) polymerizing a conjugated diene monomer or a conjugated diene monomer and an aromatic vinyl monomer using a hydrocarbon solvent in presence of an organo-alkali metal compound, thus forming an active polymer having an alkali metal end; and
b) coupling or linking the active polymer having the alkali metal end with a compound represented by Chemical Formula 1 below, yielding a modified conjugated diene-based polymer, which is a compound represented by Chemical Formula 2 below:
wherein R1 is
or a C1-C50 alkyl group, n is 1 to 20, and m is 0 to 20; and
wherein R2 is
or a C1-C50 alkyl group, Pn and Pm are polymers comprising a conjugated diene monomer and a conjugated aromatic monomer as main components, with a number average molecular weight of 1,000 to 10,000,000 g/mol, and including an acryl, amine, ether or thioether monomer, Pn and Pm are identical to or different from each other, a is 1 to 3, b is 0 to 3, n is 1 to 20, and m is 0 to 20.

### Claim 4 (depends on 3)

The method of claim 3, wherein the compound represented by Chemical Formula 1 is a compound represented by Chemical Formula 1a below

### Claim 5 (depends on 3)

The method of claim 3, wherein the compound represented by Chemical Formula 2 is a compound represented by Chemical Formula 2a below:
wherein a1 to a8 each range from 10 to 100,000.

### Claim 6 (depends on 3)

The method of claim 3, wherein the organo-alkali metal compound is used in an amount of 0.01 to 10 mmol based on 100 g in total of the monomer.

### Claim 7 (depends on 3)

The method of claim 3, wherein a molar ratio of the organo-alkali metal compound and the compound represented by Chemical Formula 1 is 1:0.1 to 1:10.

### Claim 8 (depends on 3)

The method of claim 3, wherein the polymerizing in a) is performed with additional use of a polar additive.

### Claim 9 (depends on 8)

The method of claim 8, wherein the polar additive is added in an amount of 0.001 to 50 g based on 1 mmol in total of the compound represented by Chemical Formula 1.

### Claim 10

A modifier, which is a compound represented by Chemical Formula 1 below:
wherein R1 is
or a C1-C50 alkyl group, n is 1 to 20, and m is 0 to 20.

### Claim 11 (depends on 10)

The modifier of claim 10, wherein the compound represented by Chemical Formula 1 is a compound represented by Chemical Formula 1a below

### Claim 12 (depends on 0, 1)

A modified conjugated diene-based polymer rubber composition, comprising 10 to 100 parts by weight of the modified conjugated diene-based polymer of claim 1 and 0.1 to 200 parts by weight of an inorganic filler based on 100 parts by weight of the modified conjugated diene-based polymer.

### Claim 13 (depends on 12)

The modified conjugated diene-based polymer rubber composition of claim 12, wherein the inorganic filler comprises at least one of carbon black and silica.

### Claim 14

A tire or tire tread, comprising the modified conjugated diene-based polymer rubber composition of claimed 12.
