Modification initiator and modified conjugated diene-based polymer including the same

Patent metadata

Field	Value
Publication number	US-10995157-B2
Application number	US-201716083730-A
Country	US
Kind code	B2
Filing date	Sep 29, 2017
Priority date	Oct 4, 2016
Publication date	May 4, 2021
Grant date	May 4, 2021

Abstract

The present invention relates to a modification initiator and a modified conjugated diene-based polymer including the same, and more particularly, the present invention provides a modification initiator including a compound represented by Formula 1, a modified conjugated diene-based polymer including the same, and a method of preparing a modified conjugated diene-based polymer.

First claim

The invention claimed is:

1. A modified conjugated diene-based polymer comprising a conjugated diene-based monomer-derived repeating unit, and a modification initiator-derived function group including a compound represented by Formula 1 at one end,

wherein, in Formula 1,
Y 1 and Y 2 are each independently M or R 15 , wherein Y 2 is R 15 when Y 1 is M, and Y 2 is M when Y 1 is R 15 ,
M is an alkali metal,
R 1 , R 2 and R 15 are each independently hydrogen; an alkyl group having 1 to 30 carbon atoms; an alkenyl group having 2 to 30 carbon atoms; an alkynyl group having 2 to 30 carbon atoms; a heteroalkyl group having 1 to 30 carbon atoms which includes a nitrogen (N), oxygen (O), or sulfur (S) atom; a heteroalkenyl group having 2 to 30 carbon atoms which includes an N, O, or S atom; a heteroalkynyl group having 2 to 30 carbon atoms which includes an N, O, or S atom; a cycloalkyl group having 5 to 30 carbon atoms; an aryl group having 5 to 30 carbon atoms; or a heterocyclic group having 3 to 30 carbon atoms which includes at least one of N, O, and S atoms,
R 3 is hydrogen,
R 4 is a single bond; an alkylene group having 1 to 20 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, or an aryl group having 5 to 20 carbon atoms; a cycloalkylene group having 5 to 20 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, or an aryl group having 5 to 20 carbon atoms; or an arylene group having 5 to 20 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, or an aryl group having 5 to 20 carbon atoms,
R 5 is an alkyl group having 1 to 30 carbon atoms; an alkenyl group having 2 to 30 carbon atoms; an alkynyl group having 2 to 30 carbon atoms; a heteroalkyl group having 1 to 30 carbon atoms which includes an N, O, or S atom; a heteroalkenyl group having 2 to 30 carbon atoms which includes an N, O, or S atom; a heteroalkynyl group having 2 to 30 carbon atoms which includes an N, O, or S atom; a cycloalkyl group having 5 to 30 carbon atoms; an aryl group having 5 to 30 carbon atoms; a heterocyclic group having 3 to 30 carbon atoms which includes at least one of N, O, and S atoms; a functional group represented by Formula 2; or a functional group represented by Formula 3,
n is an integer selected from 1 to 5, at least one of R 5 is the functional group represented by Formula 2 or 3, and a plurality of R 5 are the same or different from each other when n is an integer selected from 2 to 5,

wherein, in Formulae 2 and 3,
R 6 and R 10 are each independently an alkylene group having 1 to 20 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, or an aryl group having 5 to 20 carbon atoms; a cycloalkylene group having 5 to 20 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, or an aryl group having 5 to 20 carbon atoms; or an arylene group having 5 to 20 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, or an aryl group having 5 to 20 carbon atoms,
R 7 , R 8 , and R 12 are each independently an alkylene group having 1 to 20 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, or an aryl group having 5 to 20 carbon atoms,
R 9 is an alkyl group having 1 to 30 carbon atoms; an alkenyl group having 2 to 30 carbon atoms; an alkynyl group having 2 to 30 carbon atoms; a heteroalkyl group having 1 to 30 carbon atoms which includes an N, O, or S atom; a heteroalkenyl group having 2 to 30 carbon atoms which includes an N, O, or S atom; a heteroalkynyl group having 2 to 30 carbon atoms which includes an N, O, or S atom; a cycloalkyl group having 5 to 30 carbon atoms; an aryl group having 5 to 30 carbon atoms; a heterocyclic group having 3 to 30 carbon atoms which includes at least one of N, O, and S atoms; an alkenyl group having 2 to 30 carbon atoms which is substituted with an alkyl group having 1 to 10 carbon atoms which includes an alkali metal; or an aryl group having 6 to 30 carbon atoms which is substituted with an alkyl group having 1 to 10 carbon atoms which includes an alkali metal,
R 11 , R 13 , and R 14 are each independently hydrogen; an alkyl group having 1 to 30 carbon atoms; an alkenyl group having 2 to 30 carbon atoms; an alkynyl group having 2 to 30 carbon atoms; a heteroalkyl group having 1 to 30 carbon atoms which includes an N, O, or S atom; a heteroalkenyl group having 2 to 30 carbon atoms which includes an N, O, or S atom; a heteroalkynyl group having 2 to 30 carbon atoms which includes an N, O, or S atom; a cycloalkyl group having 5 to 30 carbon atoms; an aryl group having 5 to 30 carbon atoms; a heterocyclic group having 3 to 30 carbon atoms which includes at least one of N, O, and S atoms; an alkenyl group having 2 to 30 carbon atoms which is substituted with an alkyl group having 1 to 10 carbon atoms which includes an alkali metal; or an aryl group having 6 to 30 carbon atoms which is substituted with an alkyl group having 1 to 10 carbon atoms which includes an alkali metal,
X 1 and X 2 are each independently one selected from N, O, and S atoms, R 9 is not present when X 1 is an O or S atom, R 14 is not present when X 2 is an O or S atom, and
m is an integer of 1 or 2.

2. The modified conjugated diene-based polymer of claim 1 , further comprising an aromatic vinyl monomer-derived repeating unit.

3. The modified conjugated diene-based polymer of claim 1 , wherein the modified conjugated diene-based polymer has a number-average molecular weight of 10,000 g/mol to 2,000,000 g/mol, a weight-average molecular weight of 10,000 g/mol to 3,000,000 g/mol, and a molecular weight distribution of 1.0 to 5.0.

4. The modified conjugated diene-based polymer of claim 1 , wherein the modified conjugated diene-based polymer has a Mooney viscosity of 10 to 180.

5. The modified conjugated diene-based polymer of claim 1 , wherein the modified conjugated diene-based polymer has a vinyl bond content in the conjugated diene-based monomer-derived repeating unit of 5 wt % to 50 wt % based on the modified conjugated diene-based polymer.

6. The modified conjugated diene-based polymer of claim 1 , wherein the compound represented by Formula 1 comprises one selected from the group consisting of compounds represented by Formulae 1-1 to 1-13:

wherein, in Formulae 1-1 to 1-13,
M is an alkali metal,
R 15 is hydrogen; an alkyl group having 1 to 30 carbon atoms; an alkenyl group having 2 to 30 carbon atoms; and an alkynyl group having 2 to 30 carbon atoms, and
R 24 is hydrogen or an alkyl group having 1 to 8 carbon atoms.

7. The modified conjugated diene-based polymer of claim 1 , further comprising a modifier-derived functional group, which includes a compound represented by Formula 4, at the o

Assignees

• Lg Chemical Ltd

Inventors

• Kim Min Soo
• Lee Soo Yong
• Choi Won Mun

Classifications

• C08F236/10

  with vinyl-aromatic monomers · CPC title

• C08F8/42

  Introducing metal atoms or metal-containing groups · CPC title

• C08C19/25 Primary

  Incorporating silicon atoms into the molecule · CPC title

• C07F7/0834 Primary

  Compounds having one or more O-Si linkage (for compounds with C-O-Si linkages see C07F7/18) · CPC title

• C08F2/44

  Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers · CPC title