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

Patent metadata

Field	Value
Publication number	US-12460033-B2
Application number	US-202017606848-A
Country	US
Kind code	B2
Filing date	Sep 11, 2020
Priority date	Sep 11, 2019
Publication date	Nov 4, 2025
Grant date	Nov 4, 2025

Abstract

A modified conjugated diene-based polymer and a rubber composition including the same are disclosed herein. The modified conjugated diene-based polymer has excellent processability and good tensile strength and viscoelasticity. In some embodiments, a modified conjugated diene-based polymer includes a derived unit from a modifier, the modifier including three or more alkoxy groups bonded to silicon; a non-functional chain forming a silicon-carbon bond at one side of the derived unit from a modifier and including a repeating unit derived from a conjugated diene-based monomer; and a functional chain forming a silicon-carbon bond at the other side of the derived unit from a modifier and including two or more derived units from an N-functional group-containing monomer.

First claim

The invention claimed is:

1 . A modified conjugated diene-based polymer, comprising:
a derived unit from a modifier, wherein the modifier comprising three or more alkoxy groups bonded to silicon; a non-functional chain forming a silicon-carbon bond at one side of the derived unit from a modifier, wherein the non-functional chain comprising a repeating unit derived from a conjugated diene-based monomer; a functional chain forming a silicon-carbon bond at the other side of the derived unit from a modifier, wherein the functional chain comprising two or more derived units from an N-functional group-containing monomer; and wherein the non-functional chain further comprises a repeating unit derived from an aromatic vinyl-based monomer, wherein the modified conjugated diene-based polymer has a nitrogen (N) content, based on weight, of 150 ppm or more, wherein the N-functional group containing monomer is selected from:

wherein, X is N or CH, R8a to R8c are each independently a hydrogen atom; an alkyl group of 1 to 20 carbon atoms; an alkenyl group of 2 to 20 carbon atoms; an alkynyl group of 2 to 20 carbon atoms; a heteroalkyl group of 1 to 20 carbon atoms, a heteroalkenyl group of 2 to 20 carbon atoms; a heteroalkynyl group of 2 to 15 20 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, R8d is a single bond, a substituted with a substituent or unsubstituted alkylene group of 1 to 20 carbon 20 atoms; a substituted with a substituent or unsubstituted cycloalkylene group of 5 to 20 carbon atoms; or a substituted with a substituent or unsubstituted arylene group of 6 to 20 carbon atoms, 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, R8e is an alkyl group of 1 to 20 carbon atoms; an alkenyl group of 2 to 20 carbon atoms; an alkynyl group of 2 to 20 carbon atoms; a heteroalkyl group of 1 to 20 carbon atoms; a heteroalkenyl group of 2 to 20 carbon atoms; a heteroalkynyl group of 2 to 20 carbon atoms; a cycloalkyl 10 group of 5 to 20 carbon atoms; an aryl group of 6 to 20 carbon atoms; a heterocyclic group of 3 to 20 carbon atoms; or a functional group represented by Formula 1a, and O is an integer of 0 to 5, at least one R8e is a functional group represented by Formula 1a, and if o is 15 an integer of 2 to 5, multiple R8e groups may be the same or different, in Formula 1a, R8f is a single bond, a substituted with a substituent or unsubstituted alkylene group of 1 to 20 carbon atoms; a substituted with a substituent or unsubstituted cycloalkylene group of 5 to 20 carbon atoms; or a substituted with a substituent or unsubstituted arylene group of 6 to 20 carbon atoms, 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 R8g and R8h are each independently an alkyl group of 1 to 20 carbon atoms; an alkenyl group of 2 to 20 carbon atoms; an alkynyl group of 2 to 20 carbon atoms; a heteroalkyl group of 1 to 20 carbon atoms; a heteroalkenyl group of 2 to 20 carbon atoms; a heteroalkynyl group of 2 to 20 carbon atoms; a cycloalkyl group of 5 to 20 carbon atoms; an aryl group of 6 to 20 carbon atoms; a heterocyclic group of 3 to 20 carbon atoms or a mono-substituted, di-substituted or trisubstituted alkylsilyl group with alkyl groups of 1 to 10 carbon atoms, or R8g and R8h are connected with each other to form a heterocyclic group of 2 to 10 carbon atoms together with N; in Formula 2, X1-X2 is CH2-CH2 or CH═CH, and X3-X4 is CH2-CH2, CH═N or N═N; in Formula 3, R11a and R11b are each independently an alkyl group of 1 to 20 carbon atoms; an alkenyl group of 2 to 20 carbon atoms; an alkynyl group of 2 to 20 carbon atoms; a heteroalkyl group of 1 to 20 carbon atoms; a heteroalkenyl group of 2 to 20 carbon atoms; a heteroalkynyl group of 2 to 10 20 carbon atoms; a cycloalkyl group of 5 to 20 carbon atoms; an aryl group of 6 to 20 carbon atoms; a heterocyclic group of 3 to 20 carbon atoms; or a functional group represented by Formula 3a below, R11c is an alkyl group of 1 to 20 carbon atoms; an alkenyl group of 2 to 20 carbon atoms; an alkynyl group of 2 to 20 carbon atoms; a heteroalkyl group of 1 to 20 carbon atoms, a heteroalkenyl group of 2 to 20 carbon atoms; a heteroalkynyl group of 2 to 20 carbon atoms; a cycloalkyl group of 5 to 20 carbon atoms; an aryl group of 6 to 20 carbon atoms; a heterocyclic group of 3 to 20 carbon atoms; or a functional group represented by Formula 3a and at least one of R11a, R11b and R11c is a functional group represented by Formula 3a below; in Formula 3a, R11d is a single bond, a substituted with a substituent or unsubstituted alkylene group of 1 to 20 carbon atoms; a substituted with a substituent or unsubstituted cycloalkylene group of 5 to 20 carbon atoms; or a substituted with a substituent or unsubstituted arylene group of 6 to 20 carbon atoms, 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 R11e and R11f are each independently an alkyl group of 1 to 20 carbon atoms; an alkenyl group of 2 to 20 carbon 15 atoms; an alkynyl group of 2 to 20 carbon atoms; a heteroalkyl group of 1 to 20 carbon atoms; a heteroalkenyl group of 2 to 20 carbon atoms; a heteroalkynyl group of 2 to 20 carbon atoms; a cycloalkyl group of 5 to 20 carbon atoms; an aryl group of 6 to 20 carbon atoms; a heterocyclic group 20 of 3 to 20 carbon atoms; or a mono-substituted, disubstituted or tri-substituted alkylsilyl group with alkyl groups of 1 to 10 carbon atoms; in Formula 4, R12a is a single bond or a substituted with a substituent or unsubstituted alkylene group of 1 to 20 carbon atoms; a substituted with a substituent or unsubstituted cycloalkylene group of 5 to 20 carbon atoms; or a substituted with a substituent or unsubstituted arylene group of 6 to 20 carbon atoms, wherein the substituent is an alkyl group of 1 to 10 carbon atoms, a cycloalkyl group of to 10 carbon atoms, or an aryl group of 6 to 20 carbon atoms, and R12b and R12c are each independently an alkyl group of 1 to 20 carbon atoms; an alkenyl group of 2 to 20 carbon 15 atoms; an alkynyl group of 2 to 20 carbon atoms; a heteroalkyl group of 1 to 20 carbon atoms; a heteroalkenyl group of 2 to 20 carbon atoms; a heteroalkynyl group of 2 to 20 carbon atoms; a cycloalkyl group of 5 to 20 carbon atoms; an aryl group of 6 to 20 carbon atoms; a heterocyclic group of 3 to 20 carbon atoms; or a mono-substituted, disubstituted or tri-substituted alkylsilyl group with alkyl groups of 1 to 10 carbon atoms.

2 . The modified conjugated diene-based polymer according to claim 1 , wherein one or more of the functional chain are bonded to the derived unit from a modifier.

3 . The modified conjugated diene-based polymer according to claim 1 , wherein the functional chain further comprises a derived unit from a conjugated diene-based monomer.

4 . The modified conjugated diene-based polymer according to claim 1 , wherein the functional chain comprises 2 to 80 units of the derived unit from an N-functional group-containing monomer.

5 . The modified conjugated diene-based polymer according to claim 1 , wherein the modifier is an amine-containing alkoxysilane-based compound or a non-amine-containing alkoxysilane-based compound, and the modifier comprises three or more alkoxysilane groups.

6 . The modified conjugated diene-based polymer according to claim 1 , wherein the modified conjugated diene-based polymer has a number average molecular weight (Mn) of 1,000 g/m

Assignees

• Lg Chemical Ltd

Inventors

• Kim Yu Jin
• Yoo Suk Joon
• Baek Geun Seung
• Kim Hyun Jun

Classifications

• C08L9/06

  Copolymers with styrene · CPC title

• C08F226/06

  by a heterocyclic ring containing nitrogen · CPC title

• C08F2/06

  Organic solvent · CPC title

• C08C19/25

  Incorporating silicon atoms into the molecule · CPC title

• C08C19/22

  Incorporating nitrogen atoms into the molecule · CPC title