Functionalized elastomer containing a sulfur group

Patent metadata

Field	Value
Publication number	US-2016177010-A1
Application number	US-201514973772-A
Country	US
Kind code	A1
Filing date	Dec 18, 2015
Priority date	Dec 19, 2014
Publication date	Jun 23, 2016
Grant date	—

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 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.

2 . The copolymer of claim 1 , wherein sentence not finished

3 . The copolymer of claim 1 , wherein greater than 80 percent by weight of cis 1,4 microstructure content.

4 . The copolymer of claim 1 , comprising at least 95 percent by weight of cis 1,4 microstructure content.

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

6 . The copolymer of claim 1 , comprising from 0.5 to 20 percent by weight of units derived from the monomer of formula I.

7 . The copolymer of claim 1 , comprising from 1 to 5 percent by weight of units derived from the monomer of formula I.

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

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

11 . A pneumatic tire comprising the rubber composition of claim 10 .

12 . 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.

13 . The method of claim 10 , wherein the monomer of formula I is selected from the group consisting of the following structures

14 . The method of claim 12 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

• C08L47/00

  Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds; Compositions of derivatives of such polymers (C08L45/00 takes precedence; of conjugated diene rubbers C08L9/00 - C08L21/00) · CPC title

• C08F36/04

  conjugated · CPC title

• C08F236/14

  containing elements other than carbon and hydrogen · CPC title

• B60C1/0016

  Compositions of the tread · CPC title

• C08F4/619

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