Functionalized elastomer containing a boron group

Patent metadata

Field	Value
Publication number	US-10081694-B2
Application number	US-201615205116-A
Country	US
Kind code	B2
Filing date	Jul 8, 2016
Priority date	Dec 19, 2014
Publication date	Sep 25, 2018
Grant date	Sep 25, 2018

Abstract

The present invention is directed to a copolymer of a first monomer and a second monomer, wherein the first monomer is selected from the group consisting of 1,3-butadiene, isoprene, and styrene; and the second monomer is of formula I or V

wherein R 1 is a covalent bond, phenylene, a linear or branched alkane diyl group containing 1 to 10 carbon atoms, or a combination of one or more phenylene groups and one or more linear or branched alkane diyl groups containing 1 to 10 carbon atoms; R 2 and R 3 are independently linear or branched alkyl groups containing 1 to 10 carbon atoms; R 4 is hydrogen or a linear or branched alkyl group containing 1 to 10 carbon atoms; and R 5 is a linear or branched alkane diyl group containing 1 to 20 carbon atoms, or a bridging aromatic group. The invention is further directed to a rubber composition including the copolymer, and a pneumatic tire containing the rubber composition. The invention is further directed to a method of making such a copolymer.

First claim

What is claimed is:

1. A copolymer of a first monomer and a second monomer, wherein the first monomer is selected from the group consisting of 1,3-butadiene, isoprene, and styrene; and the second monomer is of formula I or V

wherein R 1 is a covalent bond, phenylene, a linear or branched alkane diyl group containing 1 to 10 carbon atoms, or a combination of one or more phenylene groups and one or more linear or branched alkane diyl groups containing 1 to 10 carbon atoms; R 2 and R 3 are independently linear or branched alkyl groups containing 1 to 10 carbon atoms; R 4 is hydrogen or a linear or branched alkyl group containing 1 to 10 carbon atoms; and R 5 is a linear or branched alkane diyl group containing 1 to 20 carbon atoms, or a bridging aromatic group.

2. The copolymer of claim 1 , comprising from 0.1 to 40 percent by weight of units derived from the second monomer based on the weight of the copolymer.

3. The copolymer of claim 1 , comprising from 0.5 to 20 percent by weight of units derived from the second monomer of based on the weight of the copolymer.

4. The copolymer of claim 1 , comprising from 1 to 5 percent by weight of units derived from the second monomer based on the weight of the copolymer.

5. The copolymer of claim 1 , where R 1 is a covalent bond and the second monomer is a monomer of formula Ia or Va

R 2 and R 3 are independently linear or branched alkyl groups containing 1 to 10 carbon atoms; R 4 is hydrogen or a linear or branched alkyl group containing 1 to 10 carbon atoms; and R 5 is a linear or branched alkane diyl group containing 1 to 20 carbon atoms, or a bridging aromatic group.

6. The copolymer of claim 1 , wherein the second monomer has the structure:

7. A rubber composition comprising the copolymer of claim 1 .

8. A pneumatic tire comprising the rubber composition of claim 7 .

9. A method of making a copolymer of a first monomer and a second monomer, wherein the first monomer is selected from the group consisting of 1,3-butadiene, isoprene, and styrene; and the second monomer is of formula I or V

wherein R 1 is a covalent bond, phenylene, a linear or branched alkane diyl group containing 1 to 10 carbon atoms, or a combination of one or more phenylene groups and one or more linear or branched alkane diyl groups containing 1 to 10 carbon atoms; R 2 and R 3 are independently linear or branched alkyl groups containing 1 to 10 carbon atoms; R 4 is hydrogen or a linear or branched alkyl group containing 1 to 10 carbon atoms; and R 5 is a linear or branched alkane diyl group containing 1 to 20 carbon atoms, or a bridging aromatic group.

10. The method of claim 9 , where the monomer of formula V has the structure:

11. The method of claim 9 , where R 1 is a covalent bond and the second monomer is a monomer of formula Ia or Va

R 2 and R 3 are independently linear or branched alkyl groups containing 1 to 10 carbon atoms; R 4 is hydrogen or a linear or branched alkyl group containing 1 to 10 carbon atoms; and R 5 is a linear or branched alkane diyl group containing 1 to 20 carbon atoms, or a bridging aromatic group.

12. The method of claim 9 wherein the polymerization is done in the present of a catalyst is of formula II

where BAr F 4 — is tetrakis(3,5-bis(trifluoromethyl)phenyl) borate.

13. The method of claim 9 , wherein the bridging aromatic group is selected from the group consisting of the following structures:

Assignees

• Goodyear Tire & Rubber

Inventors

• Flook Margaret Mcguigan
• Schnetmann Inigo Gottker Genannt
• Leicht Hannes
• Mecking Stefan

Classifications

• C08F236/08

  Isoprene · CPC title

• C08F236/06 Primary

  Butadiene · CPC title

• C08F4/619

  Component covered by group C08F4/60 containing a transition metal-carbon bond {(C08F4/60003 - C08F4/60196 take precedence)} · CPC title

• C08F4/7004

  Neutral ligand · CPC title

• B60C1/00

  Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition · CPC title