Modifier, method of preparing the same, and modified conjugated diene-based polymer including the same

Patent metadata

Field	Value
Publication number	US-10745423-B2
Application number	US-201715754464-A
Country	US
Kind code	B2
Filing date	Sep 5, 2017
Priority date	Nov 21, 2016
Publication date	Aug 18, 2020
Grant date	Aug 18, 2020

Abstract

The present disclosure relates to a modifier, and more particularly, to a modifier including a compound represented by Formula 1, and a method of preparing the same. Such modifier exhibits excellent dispersibility via hydrogen bonding with an inorganic filler when mixed therewith. The present disclosure also relates to a modified conjugated diene-based polymer modified using the modifier and thus exhibiting excellent processability, high tensile strength, high wear resistance, low rolling resistance, and high wet skid resistance, and a method of preparing the modified conjugated diene-based polymer.

First claim

The invention claimed is:

1. A modifier comprising a compound represented by Formula 1:

wherein, in Formula 1, R 1 is deuterium, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 2 -C 30 alkenyl group, a substituted or unsubstituted C 2 -C 30 alkynyl group, a substituted or unsubstituted C 1 -C 30 heteroalkyl group, a substituted or unsubstituted C 5 -C 30 cycloalkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, or a substituted or unsubstituted C 3 -C 30 heterocyclic group,
R 2 is deuterium, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 1 -C 30 alkylsilyl group, a substituted or unsubstituted C 2 -C 30 alkenyl group, a substituted or unsubstituted C 2 -C 30 alkynyl group, a substituted or unsubstituted C 1 -C 30 alkoxy group, a substituted or unsubstituted C 1 -C 30 heteroalkyl group, a substituted or unsubstituted C 5 -C 30 cycloalkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 3 -C 30 heterocyclic group, or a functional group represented by Formula 1a below,
R 3 is deuterium, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 1 -C 30 alkylsilyl group, a substituted or unsubstituted C 2 -C 30 alkenyl group, a substituted or unsubstituted C 2 -C 30 alkynyl group, a substituted or unsubstituted C 1 -C 30 alkoxy group, a substituted or unsubstituted C 1 -C 30 heteroalkyl group, a substituted or unsubstituted C 5 -C 30 cycloalkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 3 -C 30 heterocyclic group, or a functional group represented by Formula 1b below,
wherein, when R 1 , R 2 , and R 3 are the substituted alkyl group, the substituted alkylsilyl group, the substituted alkenyl group, the substituted alkynyl group, the substituted alkoxy group, the substituted heteroalkyl group, the substituted cycloalkyl group, the substituted aryl group, or the substituted heterocyclic group, a substituent of the substituted alkyl group, the substituted alkylsilyl group, the substituted alkenyl group, the substituted alkynyl group, the substituted alkoxy group, the substituted heteroalkyl group, the substituted cycloalkyl group, the substituted aryl group, or the substituted heterocyclic group comprises one or more selected from the group consisting of deuterium, a halogen, a hydroxyl group, a nitro group, a cyano group, a C 1 -C 30 alkyl group, a C 1 -C 30 alkylsilyl group, a C 2 -C 30 alkenyl group, a C 2 -C 30 alkynyl group, a C 1 -C 30 alkoxy group, a substituted or unsubstituted C 1 -C 30 heteroalkyl group, a C 5 -C 30 cycloalkyl group, a C 6 -C 30 aryl group, and a C 3 -C 30 heterocyclic group, and
X is one heteroatom selected from the group consisting of nitrogen (N), oxygen (O), and sulfur (S),
wherein, when X is N, at least one of R 2 and R 3 is necessarily the functional group of Formula 1a or 1b, and
when X is O or S, only one of the R 2 and R 3 functional groups is present, wherein, when R 2 is present, R 2 is the functional group of Formula 1a, and, when R 3 is present, R 3 is the functional group of Formula 1b,

wherein, in Formulae 1a and 1b, R 4 and R 7 are each independently a C 1 -C 10 alkylene group,
R 5 , R 6 , R 8 , and R 9 are each independently a C 1 -C 30 alkyl group, a C 5 -C 30 cycloalkyl group, or a C 6 -C 30 aryl group,
m and n are each independently an integer selected from 0, 1, 2, and 3, wherein m+n≥1, and
when only one of the functional groups of Formulae 1a and 1b is present, m or n is each independently an integer selected from 1, 2, and 3, and
when X is S and R 1 is C 6 aryl group, R 4 and R 7 are each independently a C 5 -C 10 alkylene group.

2. The modifier of claim 1 , wherein, in Formula 1, R 1 is a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 2 -C 20 alkenyl group, a substituted or unsubstituted C 2 -C 20 alkynyl group, a substituted or unsubstituted C 1 -C 20 heteroalkyl group, a substituted or unsubstituted C 5 -C 20 cycloalkyl group, a substituted or unsubstituted C 6 -C 20 aryl group, or a substituted or unsubstituted C 3 -C 20 heterocyclic group,
R 2 is the functional group of Formula 1a,
R 3 is the functional group of Formula 1b,
wherein, when R 1 is the substituted alkyl group, the substituted alkenyl group, the substituted alkynyl group, the substituted heteroalkyl group, the substituted cycloalkyl group, the substituted aryl group, or the substituted heterocyclic group, a substituent of the substituted alkyl group, the substituted alkenyl group, the substituted alkynyl group, the substituted heteroalkyl group, the substituted cycloalkyl group, the substituted aryl group, or the substituted heterocyclic group comprises one or more selected from the group consisting of deuterium, a halogen, a hydroxyl group, a nitro group, a cyano group, a C 1 -C 30 alkyl group, a C 1 -C 30 alkylsilyl group, a C 2 -C 30 alkenyl group, a C 2 -C 30 alkynyl group, a C 1 -C 30 alkoxy group, a substituted or unsubstituted C 1 -C 30 heteroalkyl group, a C 5 -C 30 cycloalkyl group, a C 6 -C 30 aryl group, and a C 3 -C 30 heterocyclic group, and
X is one heteroatom selected from the group consisting of N, O, and S,
wherein, when X is O or S, only one of the R 2 and R 3 functional groups is present, and, in Formulae 1a and 1b,
R 5 , R 6 , R 8 , and R 9 are each independently a C 1 -C 20 alkyl group, a C 5 -C 20 cycloalkyl group, or a C 6 -C 20 aryl group, and
m and n are each independently an integer selected from 1, 2, and 3, and
when X is S and R 1 is C 6 aryl group, R 4 and R 7 are each independently a C 5 -C 10 alkylene group.

3. The modifier of claim 1 , wherein the compound of Formula 1 is one selected from the group consisting of compounds represented by Formulae 1-1, 1-3, 1-5, 1-6, 1-7, 1-9 and 1-11 below:

wherein, in Formulae 1-1, 1-3, 1-5, 1-6, 1-7, 1-9 and 1-11, R 13 is a C 1 -C 20 alkyl group.

4. The modifier of claim 3 , wherein R 13 is an ethyl group or a methyl group.

5. A method of preparing the modifier of claim 1 , the method comprising reacting a compound represented by Formula 2 below with a compound represented by Formula 3 below:

wherein, in Formulae 2 and 3, R 1 is deuterium, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 2 -C 30 alkenyl group, a substituted or unsubstituted C 2 -C 30 alkynyl group, a substituted or unsubstituted C 1 -C 30 heteroalkyl group, a substituted or unsubstituted C 5 -C 30 cycloalkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, or a substituted or unsubstituted C 3 -C 30 heterocyclic group,
R 2 is deuterium, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 1 -C 30 alkylsilyl group, a substituted or unsubstituted C 2 -C 30 alkenyl group, a substituted or unsubstituted C 2 -C 30 alkynyl group, a substituted or unsubstituted C 1 -C 30 alkoxy group, a substituted or unsubstituted C 1 -C 30 heteroalkyl group, a su

Assignees

• Lg Chemical Ltd

Inventors

• Mun Min Sik
• Kim No Ma
• Chai Da Won
• Lee Ho Young

Classifications

• C08F236/14

  containing elements other than carbon and hydrogen · CPC title

• C08F236/10

  with vinyl-aromatic monomers · CPC title

• C08F36/14

  containing elements other than carbon and hydrogen · CPC title

• C08F8/42

  Introducing metal atoms or metal-containing groups · CPC title

• C08F8/30 Primary

  Introducing nitrogen atoms or nitrogen-containing groups · CPC title