# US 10,118,973 B2 · Modified conjugated diene polymer, and polymer composition containing said polymer

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- Number: US 10,118,973 B2
- Document ID: US10118973B2
- Status: Granted
- Kind: B2
- Application number: 15/539,011
- Filed: 2015-12-24
- Published: 2017-12-28
- Granted: 2018-11-06
- Earliest claimed: 2014-12-25
- Assignees: Sumitomo Chemical Company, Limited
- Applicants: Sumitomo Chemical Company, Limited
- Inventors: Koichiro Tajima
- Web page: https://patentgrep.com/patent/US10118973B2

## CPC

- C08C 19/25: Incorporating silicon atoms into the molecule
- B60C 1/00: Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
- C08C 19/22: Incorporating nitrogen atoms into the molecule
- C08C 19/42: reacting with metals or metal-containing groups
- C08C 19/44: of polymers containing metal atoms exclusively at one or both ends of the skeleton
- 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)
- C08F 36/02: the radical having only two carbon-to-carbon double bonds
- C08L 15/00: Compositions of rubber derivatives (C08L11/00, C08L13/00 take precedence)
- C08K 3/36: Silica
- 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
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- Y02T: CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO TRANSPORTATION

## Abstract

There is disclosed a modified conjugated diene polymer including a structural unit derived from a compound represented by formula (1), and a structural unit derived from a conjugated diene. When n is 0, at least two of R11, R12, R13, R16, R17 and R18 are substituted amino groups, and at least one is a hydroxy group or hydrocarbyloxy group.

## Claims

### Claim 1

A modified conjugated diene polymer including a structural unit derived from a compound represented by formula (1) and a structural unit derived from a conjugated diene
wherein in formula (1),
α and β represent integers such that 1≤α≤5, 1≤β≤5 and 2≤α+β≤6 are satisfied,
n represents 0 or 1,
(i) when n is 0,
R11, R12, R13, R16, R17 and R18 each independently represent a hydrocarbyl group, substituted amino group, hydroxy group or hydrocarbyloxy group,
from among R11, R12, R13, R16, R17 and R18, at least two are substituted amino groups and at least one is a hydroxy group or hydrocarbyloxy group,
two groups selected from among R11, R12, R13, R16, R17 and R18 are optionally bonded either directly or indirectly at positions where a hydrogen atom has been removed from each group,
R15 represents an (α+β)-valent group resulting from removal of (α+β) hydrogen atoms from a hydrocarbon,
(ii) when n is 1,
R11, R12, R13, R16, R17 and R18 each independently represent a hydrocarbyl group, substituted amino group, hydroxy group or hydrocarbyloxy group,
R14 represents:
(a) a group resulting from removal of two hydrogen atoms from a hydrocarbon with an amino group or substituted amino group,
(b) a group resulting from removal of two hydrogen atoms from a hydrocarbon with a substituent including a heteroatom other than a nitrogen atom, or
(c) a hydrocarbylene group,
when R14 is (a) a group resulting from removal of two hydrogen atoms from a hydrocarbon with an amino group or substituted amino group, from among R11, R12, R13, R16, R17 and R18, at least one is a substituted amino group and at least one is a hydroxy group or hydrocarbyloxy group,
when R14 is (b) a group resulting from removal of two hydrogen atoms from a hydrocarbon with a substituent including a heteroatom other than a nitrogen atom, or (c) a hydrocarbylene group, from among R11, R12, R13, R16, R17 and R18, at least two are substituted amino groups and at least one is a hydroxy group or hydrocarbyloxy group,
at least two groups from among R11, R12, R13, R14, R16, R17 and R18 are optionally bonded either directly or indirectly at positions where a hydrogen atom has been removed from each group, and
R15 represents an (α+β)-valent group resulting from removal of (α+β) hydrogen atoms from a hydrocarbon,
wherein the modified conjugated diene polymer has a molecular chain which is a conjugated diene polymer including a structural unit derived from the conjugated diene, and the structural unit derived from the compound represented by formula (1) is chemically bound to one or both ends of the molecular chain of the modified conjugated diene polymer or is chemically bound as a side chain on the molecular chain of the modified conjugated diene polymer.

### Claim 2 (depends on 1)

The modified conjugated diene polymer according to claim 1, wherein in formula (1), n is 0, α is 1, β is 1 and R15 is a hydrocarbylene group of 1 to 20 carbon atoms.

### Claim 3 (depends on 1)

A modified conjugated diene polymer according to claim 1, wherein the compound represented by formula (1) is at least one kind of compound selected from the group consisting of 2-(bis(diethylamino)methylsilyl)-1-(dimethoxymethylsilyl)ethane and 2-(bis(diethylamino)methylsilyl)-1-(trimethoxysilyl)ethane, respectively.

### Claim 4 (depends on 1)

A modified conjugated diene polymer composition containing the modified conjugated diene polymer according to claim 1 and a reinforcing agent, wherein the content of the reinforcing agent is 10 parts by mass or greater and 150 parts by mass or lower, with respect to 100 parts by mass of the modified conjugated diene polymer.

### Claim 5 (depends on 4)

A tire including the modified conjugated diene polymer composition according to claim 4, or its vulcanizate.
