Monomer for copolymerization with alkenes, dienes, vinyl compounds and/or vinylidene compounds, method for the synthesis of a copolymer, copolymer, rubber mixture and use thereof

Patent metadata

Field	Value
Publication number	US-10494336-B2
Application number	US-201715810639-A
Country	US
Kind code	B2
Filing date	Nov 13, 2017
Priority date	May 12, 2015
Publication date	Dec 3, 2019
Grant date	Dec 3, 2019

Abstract

Disclosed are monomers for copolymerization with alkenes, dienes, vinyl compounds, and/or vinylidene compounds, a process for preparing a copolymer, a copolymer prepared by the process, a sulfur-crosslinkable rubber mixture, and the use of the sulfur-crosslinkable rubber mixture for production of motor vehicle tires. In one embodiment, the monomer has the formula A-S—P, wherein A is a chemical group containing at least one C═C aliphatic double bond, S is a sulfur atom, and P is a protecting group.

First claim

What is claimed is:

1. A monomer of formula I):
A-S—P  I)

wherein:
A is a 4-vinylbenzyl group,
S is a sulfur atom,
P is a protecting group selected from the group consisting of: S(═O) 2 —R 1 , S—C(═S)—N—R 2 R 3 , and N—R 5 R 6 ,
R 1 =alkyl, benzyl, or phenyl,

R 2 and R 3 =alkyl, benzyl, or phenyl,
R 5 =hydrogen atom (H), alkyl, benzyl, or phenyl, and
R 6 =alkyl, benzyl or phenyl.

2. The monomer of claim 1 , wherein the monomer is 4-vinylbenzyl benzenethiosulfonate.

3. A process for preparing a copolymer, which comprises:
free-radical copolymerization of the monomer of claim 1 with at least one further monomer selected from the group consisting of: alkenes, dienes, vinyl compounds, and vinylidene compounds.

4. The process of claim 3 , wherein the alkene is selected from the group consisting of: ethene, propene, butene, pentene, and hexene, wherein the diene is selected from the group consisting of: 1,3-butadiene, 2-methylbuta-1,3-diene, 2,3-dimethyl-1,3-butadiene, 1,3-pentadiene, 2,4-hexadiene, 1,3-hexadiene, 1,3-heptadiene, 1,3-octadiene, 2-methyl-2,4-pentadiene, cyclopentadiene, 2,4-hexadiene, 1,3-cyclooctadiene, and 2-chloro-1,3-butadiene, and wherein the vinyl compound is an acrylate, methacrylates, acrylic acid, methacrylic acid, and/or acrylonitrile, or wherein the vinyl compound is styrene, 2-methylstyrene, 3-methylstyrene, 4-methylstyrene, 2,4-dimethylstyrene, 2,4,6-trimethylstyrene, alpha-methylstyrene, 2,4-diisopropylstyrene, 4-tert-butylstyrene, stilbene, vinylbenzyldimethylamine, 4-vinylbenzyl dimethylaminoethyl ether, N,N-dimethylaminoethylstyrene, tert-butoxystyrene, vinylpyridine, 1,2-divinylbenzene, 1,3-divinylbenzene, and/or 1,4-divinylbenzene.

5. A process for preparing the monomer of claim 1 , which comprises:
reacting 4-vinylbenzyl chloride with sodium benzenethiosulfonate in a polar solvent with a phase transfer catalyst.

Assignees

• Continental Reifen Deutschland Gmbh

Inventors

• Herzog Katharina
• Mueller Lena
• Recker Carla
• Pruss Noa
• Conrad Cathrin Sonja
• Vana Phillipp

Classifications

• C08F212/08

  Styrene · CPC title

• B29B7/7495

  for mixing rubber · CPC title

• C07C381/04 Primary

  Thiosulfonates · CPC title

• B60C1/0016

  Compositions of the tread · CPC title

• Y02P20/55

  Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups · CPC title