IP Library Granted Patent US 9,359,462
Granted Patent B2
US 9,359,462 · App. 14/564,200 · Granted Jun 7, 2016

Modified high cis butadiene-isoprene copolymer, method for producing the same and tire having aforementioned polymer

Inventors: Chih-Cheng Lee (Tainan, TW); Hung-Jui Kuo (Tainan, TW)
Assignee: CHI MEI CORPORATION
C08F236/08B60C1/00C08C19/25C08C19/44C08F236/06C08F2410/01C08G2261/21C08G2261/726
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Quick Facts
Patent No.
US 9,359,462
App. No.
14/564,200
Granted
Jun 7, 2016
Kind
B2
Abstract

A modified high cis butadiene-isoprene copolymer, a method for producing the same, and a tire having the aforementioned polymer are provided. The method includes performing a polymerization step for forming a high cis butadiene-isoprene copolymer having an organometallic active site and reacting which copolymer with a modifier mixture via the organometallic active site for forming the modified high cis butadiene-isoprene copolymer. The modifier mixture comprises a first modifier and a second modifier. The first modifier has a chemical formula of X—R1-Si(R2) 3 , wherein X is an glycidoxy functional group, an isocyanate functional group, or a 2-(3,4-epoxycyclohexyl group), R1 is an alkylene group, and R2 is an alkyl group or an alkoxy group. The second modifier has a chemical formula of R3-Si(R4) 3 , wherein R3 is an alkoxy group or an aryloxy group, and R4 is an alkyl group, an alkoxy group, an aryloxy group or a cycloalkyl group.

Claims (16)

1. A method for producing a modified high cis butadiene-isoprene copolymer, comprising:

performing a polymerization step for forming a high cis butadiene-isoprene copolymer having an organometallic active site, wherein the organometallic active site is formed of an organometallic catalytic system, the organometallic catalytic system comprising:

rare earth metal-organic carboxylate;

organoaluminum compound having a formula of AlR 3 or HAlR 2 , wherein R is alkyl group with 1˜8 carbon atoms; and

halogen donor comprising alkylaluminum halide; and

reacting the high cis butadiene-isoprene copolymer having the organometallic active site with a modifier mixture via the organometallic active site;

wherein the modifier mixture comprises a first modifier and a second modifier;

the first modifier has a chemical formula of X—R1-Si(R2) 3 , wherein X is an glycidoxy functional group, an isocyanate functional group, or a 2-(3,4-epoxycyclohexyl group), R1 is an alkylene group with 2˜3 carbon atoms, and R2 is an alkyl group with 2˜3 carbon atoms or an alkoxy group with 1˜3 carbon atoms; and

the second modifier has a chemical formula of R3-Si(R4) 3 , wherein R3 is an alkoxy group or an aryloxy group with 1˜12 carbon atoms, and R4 is an alkyl group, an alkoxy group, an aryloxy group or a cycloalkyl group with 1˜12 carbon atoms; and

wherein the high cis butadiene-isoprene copolymer contains a butadiene structure unit and an isoprene structure unit, the high cis butadiene-isoprene copolymer contains the butadiene structure unit from 5% to 30%, and a mole ratio of the first modifier to the second modifier is 0.1:1 to 1:1.

2. The method for producing the modified high cis butadiene-isoprene copolymer according to claim 1 , wherein the first modifier comprises at least one selected from the group consisting of 2-glycidoxyethyltrimethoxysilane, 2-glycidoxyethyltriethoxysilane, (2-glycidoxyethyl)methyldimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, methyl(3-glycidoxypropyl)dimethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltriethoxysilane, 2-(3,4-epoxycyclohexyl)ethyl(methyl)dimethoxysilane, 3-isocyanatopropyltrimethoxysilane, 3-isocyanatopropyltriethoxysilane, 3-isocyanatopropylmethyldiethoxysilane, 3-isocyanatopropyltriisopropoxysilane, and a combination thereof.

3. The method for producing the modified high cis butadiene-isoprene copolymer according to claim 1 , wherein the second modifier comprises at least one selected from the group consisting of tetramethoxysilane, tetraethoxysilane, tetrapropoxysilane, tetrabutoxysilane, methyl(trimethoxy)silane, methyl(triethoxy)silane, methyl(tripropoxy)silane, ethyl(trimethoxy)silane, ethyl(triethoxy)silane, ethyl(tripropoxy)silane, propyl(trimethoxy)silane, propyl(triethoxy)silane, propyl(tripropoxy)silane, butyl(trimethoxy)silane, butyl(triethoxy)silane, butyl(tripropoxy)silane, phenyl(tri-methoxy)silane, phenyl(tri-ethoxy)silane, phenyl(tripropoxy)silane, phenyl(tri-n-butoxy)silane, dimethyldimethoxysilane, diethyldiethoxysilane, methylphenyl(dimethoxy)silane, methylphenyl(diethoxy)silane, dicyclohexyl(diphenoxy)silane, didecyl(didecoxy)silane, tetradodecoxysilane, tetraphenoxysilane, and a combination thereof.

4. A modified high cis butadiene-isoprene copolymer, wherein the modified high cis butadiene-isoprene copolymer is produced by the method according to claim 1 .

5. The modified high cis butadiene-isoprene copolymer according to claim 4 , wherein butadiene structure units and isoprene structure units in the modified high cis butadiene-isoprene copolymer contain more than 97% of a cis-1,4-structure, and a polydispersity index (PDI) of the modified high cis butadiene-isoprene copolymer is greater than 1.5 and less than 2.7.

6. The modified high cis butadiene-isoprene copolymer according to claim 4 , wherein in the modified high cis butadiene-isoprene copolymer, a content ratio of aluminum to neodymium is 1:1 to 5:1.

7. A tire, comprising the modified high cis butadiene-isoprene copolymer produced by the method according to claim 1 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 9, 2014
From: LEE, CHIH-CHENG; KUO, HUNG-JUI
To: CHI MEI CORPORATION
Reel/Frame 034434/0615 →
Priority Claims (1)
TW 102146284 A · Dec 13, 2013 · national
Continuity (1)
Related Publication 20150166707A1 · Jun 18, 2015