Modified conjugated diene-based polymer, method for preparing the same and rubber composition including the same

Patent metadata

Field	Value
Publication number	US-12359009-B2
Application number	US-202017424410-A
Country	US
Kind code	B2
Filing date	Sep 11, 2020
Priority date	Sep 11, 2019
Publication date	Jul 15, 2025
Grant date	Jul 15, 2025

Abstract

The present invention relates to a modified conjugated diene-based polymer having excellent processability and good tensile strength and viscoelasticity, and a rubber composition including the same, and provides a modified conjugated diene-based polymer including a first chain including a repeating unit derived from a conjugated diene-based monomer; a second chain including a repeating unit derived from a compound represented by Formula 1; and a derived unit from an alkoxysilane-based modifier, wherein the first chain and the second chain are coupled by the derived unit from the modifier.

First claim

The invention claimed is:

1. A modified conjugated diene-based polymer comprising:
a first chain consisting of a repeating unit derived from a conjugated diene-based monomer, or a repeating unit derived from a conjugated diene-based monomer and a repeating unit derived from an aromatic vinyl-based monomer; a second chain comprising a repeating unit derived from a compound represented by Formula 1; and a derived unit from an alkoxysilane-based modifier,
wherein the first chain and the second chain are coupled by the derived unit from the alkoxysilane-based modifier:

in Formula 1,
R 1a to R 1c 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 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,
R 1d is a single bond, or an alkylene group of 1 to 20 carbon atoms; a cycloalkylene group of 5 to 20 carbon atoms; or an arylene group of 6 to 20 carbon atoms, each of which is unsubstituted or substituted with 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 1e 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 substituent represented by the following Formula 1a:

in Formula 1a,
R 1f is a single bond, or an alkylene group of 1 to 20 carbon atoms; a cycloalkylene group of 5 to 20 carbon atoms; or an arylene group of 6 to 20 carbon atoms, each of which is unsubstituted or substituted with 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 1g and R 1h 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; or a heterocyclic group of 3 to 20 carbon atoms, or R 1g and R 1h are connected with each other, and together with N to which they are attached to form a heterocyclic group of 2 to 10 carbon atoms.

2. The modified conjugated diene-based polymer of claim 1 ,
wherein
in Formula 1,
R 1a to R 1c are each independently a hydrogen atom; 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; a heteroalkyl group of 1 to 10 carbon atoms, a heteroalkenyl group of 2 to 10 carbon atoms; a heteroalkynyl group of 2 to 10 carbon atoms; a cycloalkyl group of 5 to 10 carbon atoms; an aryl group of 6 to 10 carbon atoms; or a heterocyclic group of 3 to 10 carbon atoms,
R 1d is a single bond or an unsubstituted alkylene group of 1 to 10 carbon atoms, and
R 1e 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; a heteroalkyl group of 1 to 10 carbon atoms; a heteroalkenyl group of 2 to 10 carbon atoms; a heteroalkynyl group of 2 to 10 carbon atoms; a cycloalkyl group of 5 to 10 carbon atoms; an aryl group of 6 to 10 carbon atoms; a heterocyclic group of 3 to 10 carbon atoms; or a substituent represented by Formula 1a, and
in Formula 1a,
R 1f is a single bond or an unsubstituted alkylene group of 1 to 10 carbon atoms, and
R 1g and R 1h are each independently 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; a heteroalkyl group of 1 to 10 carbon atoms; a heteroalkenyl group of 2 to 10 carbon atoms; a heteroalkynyl group of 2 to 10 carbon atoms; a cycloalkyl group of 5 to 10 carbon atoms; an aryl group of 6 to 10 carbon atoms; or a heterocyclic group of 3 to 10 carbon atoms, or R 1g and R 1h are connected with each other, and together with N to which they are attached to form a heterocyclic group of 2 to 10 carbon atoms.

3. The modified conjugated diene-based polymer of claim 1 ,
wherein
in Formula 1,
R 1a to R 1c are each independently a hydrogen atom; or an alkyl group of 1 to 6 carbon atoms,
R 1a is a single bond or an unsubstituted alkylene group of 1 to 6 carbon atoms, and
R 1e is an alkyl group of 1 to 10 carbon atoms or a substituent represented by Formula 1a, and in Formula 1a,
R 1f is a single bond or an unsubstituted alkylene group of 1 to 6 carbon atoms, and
R 1g and R 1h are each independently an alkyl group of 1 to 10 carbon atoms; or R 1g and R 1h are connected with each other, and together with N to which they are attached to form a heterocyclic group of 2 to 6 carbon atoms.

4. The modified conjugated diene-based polymer of claim 1 , wherein the second chain further comprises a derived unit from a conjugated diene-based monomer.

5. The modified conjugated diene-based polymer of claim 1 , which has a number average molecular weight (Mn) of 1,000 g/mol to 2,000,000 g/mol, a weight average molecular weight (Mw) of 1,000 g/mol to 3,000,000 g/mol, and a peak average molecular weight (Mp) of 1,000 g/mol to 3,000,000 g/mol.

6. A method for preparing the modified conjugated diene-based polymer of claim 1 , the method comprising:
polymerizing the conjugated diene-based monomer, or the conjugated diene-based monomer and the aromatic vinyl-based monomer in the presence of a polymerization initiator in a carbon solvent to prepare an active first chain (S1);
reacting the active first chain with the alkoxysilane-based modifier to prepare a modified active first chain (S2);
adding a macromonomer comprising the repeating unit derived from the compound represented by Formula 1 after step (S2); and
reacting the modified active first chain and the macromonomer (S3).

7. The method for preparing the modified conjugated diene-based polymer of claim 6 , wherein the macromonomer further comprises a derived unit from a second conjugated diene-based monomer.

8. The method for preparing the modified conjugated diene-based polymer of claim 6 , wherein the macromonomer is prepared by a low-degree polymerization reaction of the compound represented by Formula 1, or the compound represented by Formula 1 and the second conjugated diene-based monomer in the presence of an organolithium compound in a hydrocarbon solvent.

9. The method for preparing the modified conjugated diene-based polymer of claim 6 , wherein the alkoxysilane-based modifier is used in 0.1 mol to 10 mol based on 1 mol of the polymerization initiator.

10. The method for preparing the modified conjugated diene-based polymer of claim 6 , wherein the macromonomer is used in 0.1 to 2.0 mol based on 1 mol of the polymerization initiator.

11. A rubber composition comprising the modified conjugated diene-based polymer of claim 1 , and a filler.

12. The rubber composition of claim 11 , wherein the filler is

Assignees

• Lg Chemical Ltd

Inventors

• Lee Ho Young
• Jun Jae Moon
• Oh Jung Hwan
• Shin Hye Jung
• Oh Kyoung Hwan
• Kim Hyun Jun
• Park Hyeon Jong

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