IP Library › Granted Patent US 10,906,995
Granted Patent B2
US 10,906,995 · App. 15/569,524 · Granted Feb 2, 2021

Modifier and modified and conjugated diene-based polymer prepared using the same

Inventors: Ho Young Lee (Daejeon, KR); No Ma Kim (Daejeon, KR); Ki Seok Son (Daejeon, KR); Min Sik Mun (Daejeon, KR)
C08C19/25B60C1/00C07F7/1804C08C19/22C08C19/44C08F8/00C08K3/36C08K5/544C08K5/5415C08L51/08
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Quick Facts
Patent No.
US 10,906,995
App. No.
15/569,524
Granted
Feb 2, 2021
Kind
B2
Abstract

The present invention provides a modifier including a silane-based compound of Formula 1, which may prevent the agglomeration of a filler in a rubber composition and increase the dispersibility of a filler, thereby improving the processability of a rubber composition, by easily introducing a functional group having affinity with a filler into a conjugated diene-based polymer chain, and a modified and conjugated diene-based polymer prepared using the same.

Claims (42)

1. A modified and conjugated diene-based polymer comprising a functional group which is derived from a silane-based compound of the following Formula 1:

in Formula 1,

A 1 and A 2 are each independently a divalent hydrocarbon group of 1 to 10 carbon atoms, which is unsubstituted or substituted with at least one selected from the group consisting of an alkyl group of 1 to 10 carbon atoms, a cycloalkyl group of 3 to 10 carbon atoms, an alkoxy group of 1 to 10 carbon atoms, a cycloalkoxy group of 4 to 10 carbon atoms, an aryl group of 6 to 12 carbon atoms, an aryloxy group of 6 to 12 carbon atoms, an alkanoyloxy group of 2 to 12 carbon atoms, an arylalkyloxy group of 7 to 13 carbon atoms, an arylalkyl group of 7 to 13 carbon atoms, and an alkylaryl group of 7 to 13 carbon atoms,

R 1 to R 4 are each independently a halogen group or an alkoxy group of 1 to 6 carbon atoms,

X 1 and X 2 are each independently a nitrogen-containing heterocyclic group which is unsubstituted or substituted with at least one alkyl group of 1 to 6 carbon atoms, and

n is an integer of 1 to 5.

2. The modified and conjugated diene-based polymer of claim 1 , wherein in Formula 1, X 1 and X 2 are each independently a five-member to eight-member heterocyclic group containing 1 to 3 nitrogen atoms, which is unsubstituted or substituted with at least one alkyl group of 1 to 3 carbon atoms.

3. The modified and conjugated diene-based polymer of claim 1 , wherein in Formula 1, A 1 and A 2 are each independently an alkylene group of 1 to 6 carbon atoms which is unsubstituted or substituted with at least one alkyl group of 1 to 4 carbon atoms, R 1 to R 4 are each independently a halogen group or an alkoxy group of 1 to 6 carbon atoms, and X 1 and X 2 are each independently a five-member or six-member heterocycloalkyl group or heteroaryl group containing 1 to 3 nitrogen atoms, which is unsubstituted or substituted with at least one alkyl group of 1 to 3 carbon atoms.

4. The modified and conjugated diene-based polymer of claim 1 , wherein the silane-based compound of Formula 1 is a compound of the following Formula 1a:

in Formula 1a,

A 1 and A 2 are each independently an alkylene group of 1 to 6 carbon atoms, which is unsubstituted or substituted with at least one of an alkyl group of 1 to 4 carbon atoms,

R 1 to R 4 are each independently a halogen group or an alkoxy group of 1 to 6 carbon atoms,

R a to R d are each independently an alkyl group of 1 to 3 carbon atoms,

n is an integer of 1 to 5, and p and p′ are each independently an integer of 0 to 4.

5. The modified and conjugated diene-based polymer of claim 1 , wherein the silane-based compound of Formula 1 is a compound of the following Formula 1b:

in Formula 1b,

A 1 and A 2 are each independently an alkylene group of 1 to 6 carbon atoms, which is unsubstituted or substituted with at least one of an alkyl group of 1 to 4 carbon atoms,

R 1 to R 4 are each independently a halogen group or an alkoxy group of 1 to 6 carbon atoms,

R e and R f are each independently an alkyl group of 1 to 3 carbon atoms,

n is an integer of 1 to 5, and q and q′ are each independently an integer of 0 to 3.

6. The modified and conjugated diene-based polymer of claim 1 , wherein the silane-based compound of Formula 1 is at least one among the following Formula 2 and Formula 3:

7. The modified and conjugated diene-based polymer of claim 1 , wherein the modified and conjugated diene-based polymer is a homopolymer of conjugated diene-based monomers, or a modified polymer of a copolymer of a conjugated diene-based monomer and an aromatic vinyl-based monomer.

8. The modified and conjugated diene-based polymer of claim 1 , wherein the modified and conjugated diene-based polymer has a mooney viscosity at 100° C. is from 40 to 90.

9. A method for preparing the modified and conjugated diene-based polymer of claim 1 , the method comprising:

preparing an active polymer of which at least one terminal is combined with an alkali metal by polymerizing conjugated diene-based monomers, or an aromatic vinyl-based monomer and a conjugated diene-based monomer in the presence of an organo-alkali metal compound in a hydrocarbon solvent; and

reacting the active polymer with a modifier comprising a silane-based compound of the following Formula 1:

in Formula 1,

A 1 and A 2 are each independently a divalent hydrocarbon group of 1 to 10 carbon atoms, which is unsubstituted or substituted with at least one selected from the group consisting of an alkyl group of 1 to 10 carbon atoms, a cycloalkyl group of 3 to 10 carbon atoms, an alkoxy group of 1 to 10 carbon atoms, a cycloalkoxy group of 4 to 10 carbon atoms, an aryl group of 6 to 12 carbon atoms, an aryloxy group of 6 to 12 carbon atoms, an alkanoyloxy group of 2 to 12 carbon atoms, an arylalkyloxy group of 7 to 13 carbon atoms, an arylalkyl group of 7 to 13 carbon atoms, and an alkylaryl group of 7 to 13 carbon atoms,

R 1 to R 4 are each independently a halogen group or an alkoxy group of 1 to 6 carbon atoms,

X 1 and X 2 are each independently a nitrogen-containing heterocyclic group which is unsubstituted or substituted with at least one alkyl group of 1 to 6 carbon atoms, and

n is an integer of 1 to 5.

10. The method for preparing the modified and conjugated diene-based polymer of claim 9 , wherein a polar additive is further added during polymerizing.

11. A modifier comprising a silane-based compound of the following Formula 1:

in Formula 1,

A 1 and A 2 are each independently a divalent hydrocarbon group of 1 to 10 carbon atoms, which is unsubstituted or substituted with at least one selected from the group consisting of an alkyl group of 1 to 10 carbon atoms, a cycloalkyl group of 3 to 10 carbon atoms, an alkoxy group of 1 to 10 carbon atoms, a cycloalkoxy group of 4 to 10 carbon atoms, an aryl group of 6 to 12 carbon atoms, an aryloxy group of 6 to 12 carbon atoms, an alkanoyloxy group of 2 to 12 carbon atoms, an arylalkyloxy group of 7 to 13 carbon atoms, an arylalkyl group of 7 to 13 carbon atoms, and an alkylaryl group of 7 to 13 carbon atoms,

R 1 to R 4 are each independently a halogen group or an alkoxy group of 1 to 6 carbon atoms,

X 1 and X 2 are each independently a nitrogen-containing heterocyclic group which is unsubstituted or substituted with at least one alkyl group of 1 to 6 carbon atoms, and

n is an integer of 1 to 5.

12. A rubber composition comprising the modified and conjugated diene-based polymer according to claim 1 .

13. The rubber composition of claim 12 , wherein the rubber composition further comprises a filler in an amount of 0.1 parts by weight to 150 parts by weight based on 100 parts by weight of the modified and conjugated diene-based polymer.

14. The rubber composition of claim 13 , wherein the filler is a silica-based filler.

15. A tire manufactured from the rubber composition of claim 12 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 1, 2017
From: LEE, HO YOUNG; KIM, NO MA; SON, KI SEOK; MUN, MIN SIK
To: LG CHEM, LTD.
Reel/Frame 044008/0147 →
Priority Claims (1)
KR 10-2016-0054884 · May 3, 2016 · national
Continuity (1)
Related Publication 20180223006A1 · Aug 9, 2018
Cited By (1)
US 12,311,701