Functionalized elastomer containing a sulfur group

Patent metadata

Field	Value
Publication number	US-9994663-B2
Application number	US-201514973772-A
Country	US
Kind code	B2
Filing date	Dec 18, 2015
Priority date	Dec 19, 2014
Publication date	Jun 12, 2018
Grant date	Jun 12, 2018

Abstract

The present invention is directed to a copolymer of a monomer selected from the group consisting of 1,3-butadiene and isoprene, and a monomer of formula I

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; and R 2 is hydrogen or a linear or branched alkyl group containing 1 to 10 carbon atoms; and X is a sulfur atom or a structure of formula II or III, wherein when X is of formula III, the S atom of formula III is adjacent to the phenyl ring of formula I and the N atom of formula III is adjacent to R1

First claim

What is claimed is:

1. A copolymer of a first monomer selected from the group consisting of 1,3-butadiene and isoprene, and a second monomer of formula I

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; and R 2 is hydrogen or a linear or branched alkyl group containing 1 to 10 carbon atoms; and X is a sulfur atom or a structure of formula II or III, wherein when X is of formula III, the S atom of formula III is adjacent to the phenyl ring of formula I and the N atom of formula III is adjacent to R1

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

5. The copolymer of claim 1 , wherein the monomer of formula I is selected from the group consisting of the following structures:

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

7. A pneumatic tire comprising the rubber composition of claim 6 .

8. A method of making a copolymer, comprising the step of polymerizing a monomer selected from the group consisting of 1,3-butadiene and isoprene and a monomer of formula I in the presence of an (allyl)(arene)Ni(II) polymerization catalyst

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; and R 2 is hydrogen or a linear or branched alkyl group containing 1 to 10 carbon atoms; and X is a sulfur atom or a structure of formula II or III, wherein when X is of formula III, the S atom of formula III is adjacent to the phenyl ring of formula I and the N atom of formula III is adjacent to R1

9. The method of claim 8 , wherein the monomer of formula I is selected from the group consisting of the following structures:

10. The method of claim 8 wherein the polymerization catalyst is of formula IV

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

Assignees

• Goodyear Tire & Rubber

Inventors

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

Classifications

• C08F236/08

  Isoprene · CPC title

• C08F36/06

  Butadiene · CPC title

• B60C1/00

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

• C08F36/08

  Isoprene · CPC title

• C08F36/14 Primary

  containing elements other than carbon and hydrogen · CPC title