Polymer compound, method for preparing modified and conjugated diene-based polymer using the same, and modified and conjugated diene-based polymer

Patent metadata

Field	Value
Publication number	US-10829627-B2
Application number	US-201615749195-A
Country	US
Kind code	B2
Filing date	Dec 22, 2016
Priority date	Dec 24, 2015
Publication date	Nov 10, 2020
Grant date	Nov 10, 2020

Abstract

The present invention relates to a polymer compound used as a polymer modifier, a conjugated diene-based polymer including a functional group derived therefrom, and a method for preparing a modified and conjugated diene-based polymer using the polymer compound. A rubber modifier compound obtained therefrom is used as a modifier for rubber, particularly, as a modifier of a conjugated diene-based polymer and is bonded to a chain of the conjugated diene-based polymer to easily introduce a functional group having affinity with a filler.

First claim

The invention claimed is:

1. A polymer compound comprising a constituent unit represented by the following Formula 1:

in Formula 1,
X 1 and X 2 are each independently a derived substituent from a compound containing C 1-10 alkyl, amine, ester, nitrile, benzophenone, acryl, vinyl, styrene, styrenacryl, or aryl, which is unsubstituted or substituted with at least one substituent selected from the group consisting of halogen, C 1-20 alkyl, C 3-20 cycloalkyl, and C 6-30 aryl, wherein the C 1-20 alkyl, C 3-20 cycloalkyl, and C 6-30 aryl is optionally substituted with a halogen,
X 3 is represented by the following Formula 2:

in Formula 2,
R 1 is ester,
R 2 is C 1-20 alkyl, and
a is an integer of 1 to 10,
X 4 is represented by the following Formula 3:

in Formula 3,
R 3 is C 1-6 alkylene, ester, or C 6-10 arylene,
R 4 and R 5 are each independently C 1-10 alkyl, or are combined with each other to form a C 3-10 ring structure, and
b is an integer of 1 to 8,
m, n, o and p represent a molar ratio of each repeating unit, where m+n+o+p is 100,
m is 1 to 50,
n is 0 to 50,
o is 1 to 50,
p is 1 to 70, and
A 1 to A 4 are each independently a hydrogen atom, or C 1-3 alkyl,
wherein X 1 to X 4 are different from each other.

2. The polymer compound of claim 1 , wherein in Formula 1, X 1 is C 1-10 alkyl, ester or alkylaryl substituted with halogen.

3. The polymer compound of claim 1 , wherein in Formula 1, X 2 is C 6-10 aryl unsubstituted or substituted with C 1-3 alkyl or C 3-10 cycloalkyl.

4. The polymer compound of claim 1 , wherein the polymer compound comprising the constituent unit represented by Formula 1 comprises a constituent unit represented by the following Formula 4 or Formula 5:

in Formula 4 and Formula 5,
m, n, o and p represent a molar ratio of each repeating unit, where m+n+o+p is 100,
m is 1 to 50,
n is 0 to 50,
o is 1 to 50, and
p is 1 to 70.

5. The polymer compound of claim 1 , wherein the polymer compound is a modifier for a conjugated diene-based polymer.

6. A modified and conjugated diene-based polymer comprising a functional group derived from a polymer compound comprising a constituent unit represented by the following Formula 1:

in Formula 1,
X 1 and X 2 are each independently a derived substituent from a compound containing C 1-10 alkyl, amine, ester, nitrile, benzophenone, acryl, vinyl, styrene, styrenacryl, or aryl, which is unsubstituted or substituted with at least one substituent selected from the group consisting of halogen, C 1-20 alkyl, C 3-20 cycloalkyl, and C 6-30 aryl, wherein the C 1-20 alkyl, C 3-20 cycloalkyl, and C 6-30 aryl is optionally substituted with a halogen,
X 3 is represented by the following Formula 2:

in Formula 2,
R 1 is ester,
R 2 is C 1-20 alkyl, and
a is an integer of 0 to 10,
X 4 is represented by the following Formula 3:

in Formula 3,
R 3 is C 1-6 alkylene, ester, or C 6-10 arylene,
R 4 and R 5 are each independently C 1-10 alkyl, or are combined with each other to form a C 3-10 ring structure, and
b is an integer of 1 to 8,
m, n, o and p represent a molar ratio of each repeating unit, where m+n+o+p is 100,
m is 1 to 50,
n is 0 to 50,
o is 1 to 50,
p is 1 to 70, and
A 1 to A 4 are each independently a hydrogen atom, or C 1-3 alkyl.

7. The modified and conjugated diene-based polymer of claim 6 , wherein the polymer compound comprising the constituent unit represented by Formula 1 comprises a constituent unit represented by the following Formula 4 or Formula 5:

in Formula 4 and Formula 5,
m, n, o and p represent a molar ratio of each repeating unit, where m+n+o+p is 100,
m is 1 to 50,
n is 0 to 50,
o is 1 to 50, and
p is 1 to 70.

8. The modified and conjugated diene-based polymer of claim 6 , wherein the polymer comprises from 100 ppm to 10,000 ppm of a silane group based on a total amount of the polymer.

9. The modified and conjugated diene-based polymer of claim 6 , wherein the polymer comprises 40 wt % or less of a derived unit from an aromatic vinyl-based monomer.

10. The modified and conjugated diene-based polymer of claim 6 , wherein the polymer has a number average molecular weight of 10,000 g/mol to 1,000,000 g/mol.

11. A method for preparing the modified and conjugated diene-based polymer of claim 6 , the method comprising:
1) polymerizing conjugated diene-based monomers, or an aromatic vinyl-based monomer and a conjugated diene-based monomer in the presence of an organo-alkali metal compound in a hydrocarbon solvent to prepare an active polymer in which an alkali metal is bonded to at least one terminal thereof;
2) reacting the active polymer with a polymer compound comprising a constituent unit represented by the following Formula 1 to obtain a first modified polymer; and
3) reacting the first modified polymer with a silane-based compound:

in Formula 1,
X 1 and X 2 are each independently a derived substituent from a compound containing C 1-10 alkyl, amine, ester, nitrile, benzophenone, acryl, vinyl, styrene, styrenacryl, or aryl, which is unsubstituted or substituted with at least one substituent selected from the group consisting of halogen, C 1-20 alkyl, C 3-20 cycloalkyl, and C 6-30 aryl, wherein the C 1-20 alkyl, C 3-20 cycloalkyl, and C 6-30 aryl is optionally substituted with a halogen,
X 3 is represented by the following Formula 2:

in Formula 2,
R 1 is ester,
R 2 is C 1-20 alkyl, and
a is an integer of 0 to 10,
X 4 is represented by the following Formula 3:

in Formula 3,
R 3 is C 1-6 alkylene, ester, or C 6-10 arylene,
R 4 and R 5 are each independently C 1-10 alkyl, or are combined with each other to form a C 3-10 ring structure, and
b is an integer of 1 to 8,
m, n, o and p represent a molar ratio of each repeating unit, where m+n+o+p is 100,
m is 1 to 50,
n is 0 to 50,
o is 1 to 50,
p is 1 to 70, and
A 1 to A 4 are each independently a hydrogen atom, or C 1-3 alkyl.

12. The method for preparing the modified and conjugated diene-ba

Assignees

• Lg Chemical Ltd

Inventors

• Sohn Hae Sung
• Lee He Seung
• Kim No Ma

Classifications

• C08L25/10 Primary

  with conjugated dienes · CPC title

• C08F220/281

  and containing only one oxygen, e.g. furfuryl (meth)acrylate or 2-methoxyethyl (meth)acrylate · CPC title

• C08F212/18

  Chlorine · CPC title

• C08F212/28

  Amines · CPC title

• B60C1/00 Primary

  Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition · CPC title