Modified conjugated diene-based polymer and rubber composition including the same

Patent metadata

Field	Value
Publication number	US-11414510-B2
Application number	US-201816753106-A
Country	US
Kind code	B2
Filing date	Nov 30, 2018
Priority date	Dec 5, 2017
Publication date	Aug 16, 2022
Grant date	Aug 16, 2022

Abstract

The present invention relates to a modified conjugated diene-based polymer, and more particularly, to a modified conjugated diene-based polymer prepared by continuous polymerization and having a specific polymer structure and molecular weight distribution degree and shape, and thus, having remarkable processability and narrow molecular weight distribution, and thus, having excellent physical properties, and a rubber composition including the same.

First claim

The invention claimed is:

1. A modified conjugated diene-based polymer, having a unimodal shape molecular weight distribution curve by gel permeation chromatography (GPC), and
molecular weight distribution (PDI; MWD) of 1.0 to less than 1.7, and
comprising a functional group derived from a modification initiator at one terminal and a functional group derived from a modifier represented by any one selected from the following Formula 2 to Formula 4 at the other terminal,
wherein the modification initiator is a reaction product of a compound represented by the following Formula 1 and an organometal compound,

in Formula 1,
R 1 to R 3 are each independently hydrogen; an alkyl group of 1 to 30 carbon atoms; an alkenyl group of 2 to 30 carbon atoms; an alkynyl group of 2 to 30 carbon atoms; a heteroalkyl group of 1 to 30 carbon atoms; a heteroalkenyl group of 2 to 30 carbon atoms; a heteroalkynyl group of 2 to 30 carbon atoms; a cycloalkyl group of 5 to 30 carbon atoms; an aryl group of 6 to 30 carbon atoms; or a heterocyclic group of 3 to 30 carbon atoms,
R 4 is a single bond; an alkylene group of 1 to 20 carbon atoms unsubstituted or substituted with a substituent; a cycloalkylene group of 5 to 20 carbon atoms unsubstituted or substituted with a substituent; or an arylene group of 6 to 20 carbon atoms unsubstituted or substituted with a substituent, wherein the substituent is an alkyl group of 1 to 10 carbon atoms, a cycloalkyl group of 5 to 10 carbon atoms, or an aryl group of 6 to 20 carbon atoms,
R 5 is each independently an alkyl group of 1 to 30 carbon atoms; an alkenyl group of 2 to 30 carbon atoms; an alkynyl group of 2 to 30 carbon atoms; a heteroalkyl group of 1 to 30 carbon atoms; a heteroalkenyl group of 2 to 30 carbon atoms; a heteroalkynyl group of 2 to 30 carbon atoms; a cycloalkyl group of 5 to 30 carbon atoms; an aryl group of 6 to 30 carbon atoms; a heterocyclic group of 3 to 30 carbon atoms; or a functional group represented by the following Formula 1a or Formula 1b, and
n is an integer of 1 to 5, and at least one of R 5 groups is a functional group represented by the following Formula 1a or Formula 1b, and when n is an integer of 2 to 5, R 5 S are the same or different,

in Formula 1a,
R 6 is an alkylene group of 1 to 20 carbon atoms unsubstituted or substituted with a substituent; a cycloalkylene group of 5 to 20 carbon atoms unsubstituted or substituted with a substituent; or an arylene group of 6 to 20 carbon atoms unsubstituted or substituted with a substituent, wherein the substituent is an alkyl group of 1 to 10 carbon atoms, a cycloalkyl group of 5 to 10 carbon atoms, or an aryl group of 6 to 20 carbon atoms,
R 7 and R 8 are each independently an alkyl group of 1 to 10 carbon atoms; a cycloalkyl group of 5 to 10 carbon atoms; or an alkylene group of 1 to 20 carbon atoms unsubstituted or substituted with an aryl group of 6 to 20 carbon atoms,
R 9 is hydrogen; an alkyl group of 1 to 30 carbon atoms; an alkenyl group of 2 to 30 carbon atoms; an alkynyl group of 2 to 30 carbon atoms; a heteroalkyl group of 1 to 30 carbon atoms; a heteroalkenyl group of 2 to 30 carbon atoms; a heteroalkynyl group of 2 to 30 carbon atoms; a cycloalkyl group of 5 to 30 carbon atoms; an aryl group of 6 to 30 carbon atoms; or a heterocyclic group of 3 to 30 carbon atoms, and
X is an N, O or S atom, and when X is O or S, R 9 is not present,

in Formula 1b,
R 10 is an alkylene group of 1 to 20 carbon atoms unsubstituted or substituted with a substituent; a cycloalkylene group of 5 to 20 carbon atoms unsubstituted or substituted with a substituent; or an arylene group of 6 to 20 carbon atoms unsubstituted or substituted with a substituent, wherein the substituent is an alkyl group of 1 to 10 carbon atoms, a cycloalkyl group of 5 to 10 carbon atoms, or an aryl group of 6 to 20 carbon atoms, and
R 11 and R 12 are each independently an alkyl group of 1 to 30 carbon atoms; an alkenyl group of 2 to 30 carbon atoms; an alkynyl group of 2 to 30 carbon atoms; a heteroalkyl group of 1 to 30 carbon atoms; a heteroalkenyl group of 2 to 30 carbon atoms; a heteroalkynyl group of 2 to 30 carbon atoms; a cycloalkyl group of 5 to 30 carbon atoms; an aryl group of 6 to 30 carbon atoms; or a heterocyclic group of 3 to 30 carbon atoms,

in Formula 2,
R a1 and R a4 are each independently a single bond, or an alkylene group of 1 to 10 carbon atoms,
R a2 and R a3 are each independently an alkyl group of 1 to 10 carbon atoms,
R a5 is a five-member heterocyclic group of 2 to 4 carbon atoms comprising one or more heteroatoms selected from the group consisting of N, O and S,
n 1 is an integer of 1 to 3, and
n 2 is an integer of 0 to 2,

in Formula 3,
A 1 and A 2 are each independently an alkylene group of 1 to 20 carbon atoms,
R b1 to R b4 are each independently an alkyl group of 1 to 20 carbon atoms,
R b5 and R b6 are each independently hydrogen or an alkyl group of 1 to 10 carbon atoms, and
A 3 and A 4 are each independently

where R b7 to R b10 are each independently hydrogen or an alkyl group of 1 to 10 carbon atoms,

in Formula 4,
R c1 is hydrogen or an alkyl group of 1 to 10 carbon atoms,
R c2 to R c4 are each independently an alkylene group of 1 to 10 carbon atoms,
R c5 to R c8 are each independently an alkyl group of 1 to 10 carbon atoms,
A 5 is

where R c9 to R c12 are each independently hydrogen or an alkyl group of 1 to 10 carbon atoms, and
m 1 and m 2 are each independently an integer of 0 to 3, where an equation of m 1 +m 2 ≥1 is satisfied.

2. The modified conjugated diene-based polymer according to claim 1 , wherein
in Formula 1,
R 1 to R 3 are each independently hydrogen; an alkyl group of 1 to 10 carbon atoms; an alkenyl group of 2 to 10 carbon atoms; or an alkynyl group of 2 to 10 carbon atoms,
R 4 is a single bond; or an unsubstituted alkylene group of 1 to 10 carbon atoms, and
R 5 is an alkyl group of 1 to 10 carbon atoms; an alkenyl group of 2 to 10 carbon atoms; an alkynyl group of 2 to 10 carbon atoms; or a functional group represented by the following Formula 1a or Formula 1b,
in Formula 1a, R 6 is an unsubstituted alkylene group of 1 to 10 carbon atoms, R 7 and R 8 are each independently an unsubstituted alkylene group of 1 to 10 carbon atoms, and R 9 is an alkyl group of 1 to 10 carbon atoms; a cycloalkyl group of 5 to 20 carbon atoms; an aryl group of 6 to 20 carbon atoms; or a heterocyclic group of 3 to 20 carbon atoms, and
in Formula 1b, R 10 is an unsubstituted alkylene group of 1 to 10 carbon atoms, R 11 and R 12 are each independently an alkyl group of 1 to 10 carbon atoms; a cycloalkyl group of 5 to 20 carbon atoms; an aryl group of 6 to 20 carbon atoms; or a heterocyclic group of 3 to 20 carbon atoms.

3. The modif

Assignees

• Lg Chemical Ltd

Inventors

• Oh Jung Hwan
• Seo You Seok
• Choe Jae Hoon
• Kim Min Soo
• Kim No Ma

Classifications

• Y02T10/86

  Optimisation of rolling resistance, e.g. weight reduction · CPC title

• C08K3/36

  Silica · CPC title

• C08K3/04

  Carbon · CPC title

• C08C19/26

  Incorporating metal atoms into the molecule · CPC title

• C08L9/00

  Compositions of homopolymers or copolymers of conjugated diene hydrocarbons · CPC title