Method of preparing rubber composition including syndiotactic 1,2-polybutadiene

Patent metadata

Field	Value
Publication number	US-10745549-B2
Application number	US-201816012123-A
Country	US
Kind code	B2
Filing date	Jun 19, 2018
Priority date	Jun 19, 2017
Publication date	Aug 18, 2020
Grant date	Aug 18, 2020

Abstract

According to an embodiment of the present invention, there is provided a method of preparing a rubber composition, which includes (a) synthesizing a living polymer by solution polymerization of a monomer mixture including a conjugated diene-based monomer in the presence of a first catalyst; (b) reacting some ends of the living polymer with a coupling agent; (c) reacting the remaining ends of the living polymer with an organotin halide compound to prepare an end-modified conjugated diene-based polymer solution; and (d) adding a second catalyst and a conjugated diene-based monomer to the end-modified conjugated diene-based polymer solution to induce solution polymerization.

First claim

What is claimed is:

1. A method of preparing a rubber composition, comprising:
(a) synthesizing a living polymer by solution polymerization of a monomer mixture including a conjugated diene-based monomer in the presence of a first catalyst;
(b) reacting some ends of the living polymer with a coupling agent;
(c) reacting the remaining ends of the living polymer with an organotin halide compound to prepare an end-modified conjugated diene-based polymer solution; and
(d) adding a second catalyst and a conjugated diene-based monomer to the end-modified conjugated diene-based polymer solution to induce solution polymerization.

2. The method of claim 1 , wherein the conjugated diene-based monomer is one or more selected from the group consisting of 1,3-butadiene, 2,3-dimethyl-1,3-butadiene, piperylene, 3-butyl-1,3-octadiene, isoprene, and 2-phenyl-1,3-butadiene.

3. The method of claim 1 , wherein the monomer mixture further includes an aromatic vinyl monomer.

4. The method of claim 3 , wherein the aromatic vinyl monomer is one or more selected from the group consisting of styrene, α-methylstyrene, 3-methylstyrene, 4-methylstyrene, 2,4-dimethylstyrene, 2,4-diisopropylstyrene, 4-propylstyrene, 1-vinylnaphthalene, 4-cyclohexylstyrene, 4-(p-methylphenyl)styrene, N,N-dimethylaminoethylstyrene, and 1-vinyl-5-hexylnaphthalene.

5. The method of claim 1 , wherein the first catalyst is one or more selected from the group consisting of an organolithium compound, an organosodium compound, an organopotassium compound, an organorubidium compound, and an organocesium compound.

6. The method of claim 1 , wherein, in the step (b), 10 to 40% of the ends of the living polymer are reacted with the coupling agent.

7. The method of claim 1 , wherein the coupling agent is one or more selected from the group consisting of tin tetrachloride, silicon tetrachloride, and a silicon alkoxide.

8. The method of claim 1 , wherein the organotin halide compound is one or more selected from the group consisting of trimethyltin chloride, dibutyltin dichloride, tributyltin chloride, and phenyltin trichloride.

9. The method of claim 1 , wherein the second catalyst includes an organoaluminum compound, a phosphorus compound, and a transition metal complex.

10. The method of claim 9 , wherein the second catalyst includes 15 to 40 equivalents of the organoaluminum compound and 1 to 15 equivalents of the phosphorus compound with respect to 1 equivalent of the transition metal complex.

11. The method of claim 9 , wherein the organoaluminum compound is one or more selected from the group consisting of trimethylaluminum, triethylaluminum, tripropylaluminum, tributylaluminum, triisobutylaluminum, trihexylaluminum, and diisobutylaluminum hydride.

12. The method of claim 9 , wherein the phosphorus compound is a phosphite, a phosphate, or a mixture thereof.

13. The method of claim 9 , wherein the transition metal complex is an iron carboxylate or iron acetylacetonate.

14. The method of claim 1 , wherein the steps (a) to (d) are carried out in situ.

15. The method of claim 1 , wherein a product of the step (d) includes 60 to 90 wt % of an end-modified conjugated diene-based polymer and 10 to 40 wt % of syndiotactic 1,2-polybutadiene.

Assignees

• Korea Kumho Petrochemical Co Ltd

Inventors

• Kim Jae Yun
• Jung Yeong Min

Classifications

• B60C1/0016 Primary

  Compositions of the tread · CPC title

• C08C19/24

  Incorporating phosphorus atoms into the molecule · CPC title

• C08C19/26

  Incorporating metal atoms into the molecule · CPC title

• C08F136/06

  Butadiene · CPC title

• C08L7/00

  Compositions of natural rubber · CPC title