Polymers functionalized with protected oxime compounds containing a cyano group

Patent metadata

Field	Value
Publication number	US-10030083-B2
Application number	US-201514704318-A
Country	US
Kind code	B2
Filing date	May 5, 2015
Priority date	May 15, 2014
Publication date	Jul 24, 2018
Grant date	Jul 24, 2018

Abstract

A method for preparing a functionalized polymer, the method comprising the steps of: (i) polymerizing monomer to form a reactive polymer, and (ii) reacting the reactive polymer with a protected oxime compound containing a cyano group.

First claim

What is claimed is:

1. A method for preparing a functionalized polymer, the method comprising the steps of:
(i) polymerizing monomer to form a reactive polymer, and
(ii) reacting the reactive polymer with a protected oxime compound containing a cyano group.

2. The method of claim 1 , where the protected oxime compound containing a cyano group is defined by the formula I:

where R 1 is a hydrogen atom or monovalent organic group, R 2 is a monovalent organic group, and R 3 is a bond or a divalent organic group, or where R 1 and R 3 join to form a trivalent organic group.

3. The method of claim 2 , where the protected oxime compound containing a cyano group is defined by the formula II:

where R 2 is a monovalent organic group and R 4 is a trivalent organic group.

4. The method of claim 1 , where the protected oxime compound containing a cyano group is selected from the group consisting of cyano O-hydrocarbyloximes, cyano O-silyloximes, cyano O-sulfonyloximes, and cyano O-acyloximes.

5. The method of claim 4 , where the protected oxime compound containing a cyano group is a cyano O-hydrocarbyloxime selected from the group consisting of cyanoformaldehyde O-methyloxime, 2-cyanoacetaldehyde O-methyloxime, 2-cyanopropionaldehyde O-methyloxime, 3-cyanobutyraldehyde O-methyloxime, 3-cyanopentanaldehyde O-methyloxime, 2-cyanocyclopentanecarboxaldehyde O-methyloxime, 6-cyanohexanaldehyde O-methyloxime, 3-cyanocyclohexanecarboxaldehyde O-methyloxime, 6-cyanoheptanaldehyde O-methyloxime, 4-cyanocycloheptanecarboxaldehyde O-methyloxime, 6-cyanooctanaldehyde O-methyloxime, 4-cyanocyclooctanecarboxaldehyde O-methyloxime, 9-cyanononanaldehyde O-methyloxime, 3-cyanocyclononanecarboxaldehyde O-methyloxime, 2-cyanobenzaldehyde O-methyloxime, 3-cyanobenzaldehyde O-methyloxime, 4-cyanobenzaldehyde O-methyloxime, 4-cyano-trans-cinnamaldehyde O-methyloxime, 4-cyano-2-pyridinecarboxaldehyde O-methyloxime, 4-cyanotetrahydrofuran-3-carboxaldehyde O-methyloxime, 4-cyano-2-furancarboxaldehyde O-methyloxime, 2-cyano-3-furancarboxaldehyde O-methyloxime, 3-cyano-N-methyl-4-pyrazolecarboxaldehyde O-methyloxime, 4-cyano-N-methyl-2-pyrrolecarboxaldehyde O-methyloxime, 4-cyano-N-methyl-2-imidazolecarboxaldehyde O-methyloxime, 5-cyano-N-methyl-indole-3-carboxaldehyde O-methyloxime, 5-cyano-N-methyl-1,2,3-triazole-4-carboxaldehyde O-methyloxime, 5-cyano-N-methyl-1,2,4-triazole-3-carboxaldehyde O-methyloxime, 3-cyanopyrazinecarboxaldehyde O-methyloxime, 4-cyano-2-thiazolecarboxaldehyde O-methyloxime, 4-cyano-2-thiophenecarboxaldehyde O-methyloxime, cyanoformaldehyde O-benzyloxime, 2-cyanoacetaldehyde O-benzyloxime, 2-cyanopropionaldehyde O-benzyloxime, 3-cyanobutyraldehyde O-benzyloxime, 3-cyanopentanaldehyde O-benzyloxime, 2-cyanocyclopentanecarboxaldehyde O-benzyloxime, 6-cyanohexanaldehyde O-benzyloxime, 3-cyanocyclohexanecarboxaldehyde O-benzyloxime, 6-cyanoheptanaldehyde O-benzyloxime, 4-cyanocycloheptanecarboxaldehyde O-benzyloxime, 6-cyanooctanaldehyde O-benzyloxime, 4-cyanocyclooctanecarboxaldehyde O-benzyloxime, 9-cyanononanaldehyde O-benzyloxime, 3-cyanocyclononanecarboxaldehyde O-benzyloxime, 2-cyanobenzaldehyde O-benzyloxime, 3-cyanobenzaldehyde O-benzyloxime, 4-cyanobenzaldehyde O-benzyloxime, 4-cyano-trans-cinnamaldehyde O-benzyloxime, 4-cyano-2-pyridinecarboxaldehyde O-benzyloxime, 4-cyanotetrahydrofuran-3-carboxaldehyde O-benzyloxime, 4-cyano-2-furancarboxaldehyde O-benzyloxime, 2-cyano-3-furancarboxaldehyde O-benzyloxime, 3-cyano-N-methyl-4-pyrazolecarboxaldehyde O-benzyloxime, 4-cyano-N-methyl-2-pyrrolecarboxaldehyde O-benzyloxime, 4-cyano-N-methyl-2-imidazolecarboxaldehyde O-benzyloxime, 5-cyano-N-methyl-indole-3-carboxaldehyde O-benzyloxime, 5-cyano-N-methyl-1,2,3-triazole-4-carboxaldehyde O-benzyloxime, 5-cyano-N-methyl-1,2,4-triazole-3-carboxaldehyde O-benzyloxime, 3-cyanopyrazinecarboxaldehyde O-benzyloxime, 4-cyano-2-thiazolecarboxaldehyde O-benzyloxime, 4-cyano-2-thiophenecarboxaldehyde O-benzyloxime, 1-cyano-2-propanone O-methyloxime, 4-cyano-2-butanone O-methyloxime, 3-cyano-2-pentanone O-methyloxime, 1-cyano-3-pentanone O-methyloxime, 4-cyano-2-hexanone O-methyloxime, 1-cyano-3-hexanone O-methyloxime, 4-cyano-2-heptanone O-methyloxime, 1-cyano-3-heptanone O-methyloxime, 1-cyano-4-heptanone O-methyloxime, 5-cyano-2-octanone O-methyloxime, 5-cyano-3-octanone O-methyloxime, 9-cyano-2-nonanone O-methyloxime, 6-cyano-3-nonanone O-methyloxime, 1-cyano-5-nonanone O-methyloxime, 1-(2-cyanophenyl)ethan-1-one O-methyloxime, 1-(3-cyanophenyl)ethan-1-one O-methyloxime, 1-(4-cyanophenyl)ethan-1-one O-methyloxime, 1-(2-cyanocyclohexyl)ethan-1-one O-methyloxime, 1-(3-cyanocyclohexyl)ethan-1-one O-methyloxime, 1-(4-cyanocyclohexyl)ethan-1-one O-methyloxime, 2-cyanoacetophenone O-methyloxime, 3-cyanobenzophenone O-methyloxime, 4-cyanobenzophenone O-methyloxime, 2-cyanocyclobutanone O-methyloxime, 3-cyanocyclopentanone O-methyloxime, 2-cyanocyclohexanone O-methyloxime, 3-cyanocycloheptanone O-methyloxime, 4-cyanocyclooctanone O-methyloxime, 3-cyanocyclononanone O-methyloxime, 2-cyanocyclodecanone O-methyloxime, 4-cyanocycloundecanone O-methyloxime, 3-cyanocyclododecanone O-methyloxime, 4-cyanocyclotridecanone O-methyloxime, 4-cyano-1,3-dimethyl-2-imidazolidinone O-methyloxime, 1-(3-cyanothiophen-2-yl)ethan-1-one O-methyloxime, 1-(4-cyanothiazol-2-yl)ethan-1-one O-methyloxime, 1-(3-cyanopyridin-2-yl)ethan-1-one O-methyloxime, 1-(4-cyanopyridin-3-yl)ethan-1-one O-methyloxime, 1-(3-cyanopyridin-4-yl)ethan-1-one O-methyloxime, 4-cyano-bis(2-pyridyl)ketone O-methyloxime, 1-(3-cyano-1-methylpyrrolyl)ethan-1-one O-methyloxime, 1-(2-cyano-1-methylpyrrolyl)ethan-1-one O-methyloxime, 1-cyano-2-propanone O-benzyloxime, 4-cyano-2-butanone O-benzyloxime, 3-cyano-2-pentanone O-benzyloxime, 1-cyano-3-pentanone O-benzyloxime, 4-cyano-2-hexanone O-benzyloxime, 1-cyano-3-hexanone O-benzyloxime, 4-cyano-2-heptanone O-benzyloxime, 1-cyano-3-heptanone O-benzyloxime, 1-cyano-4-heptanone O-benzyloxime, 5-cyano-2-octanone O-benzyloxime, 5-cyano-3-octanone O-benzyloxime, 9-cyano-2-nonanone O-benzyloxime, 6-cyano-3-nonanone O-benzyloxime, 1-cyano-5-nonanone O-benzyloxime, 1-(2-cyanophenyl)ethan-1-one O-benzyloxime, 1-(3-cyanophenyl) ethan-1-one O-benzyloxime, 1-(4-cyanophenyl)ethan-1-one O-benzyloxime, 1-(2-cyanocyclohexyl)ethan-1-one O-benzyloxime, 1-(3-cyanocyclohexyl)ethan-1-one O-benzyloxime, 1-(4-cyanocyclohexyl)ethan-1-one O-benzyloxime, 2-cyanoacetophenone O-benzyloxime, 3-cyanobenzophenone O-benzyloxime, 4-cyanobenzophenone O-benzyloxime, 2-cyanocyclobutanone O-benzyloxime, 3-cyanocyclopentanone O-benzyloxime, 2-cyanocyclohexanone O-benzyloxime, 3-cyanocycloheptanone O-benzyloxime, 4-cyanocyclooctanone O-benzyloxime, 3-cyanocyclononanone O-benzyloxime, 2-cyanocyclodecanone O-benzyloxime, 4-cyanocycloundecanone O-benzyloxime, 3-cyanocyclododecanone O-benzyloxime, 4-cyanocyclotridecanone O-benzyloxime, 4-cyano-1,3-dimethyl-2-imidazolidinone O-benzyloxime, 1-(3-cyanothiophen-2-yl)ethan-1-one O-benzyloxime, 1-(4-cyanothiazol-2-yl)ethan-1-one O-benzyloxime, 1-(3-cyanopyridin-2-yl)ethan-1-one O-benzyloxime, 1-(4-cyanopyridin-3-yl)ethan-1-one O-benzyloxime, 1-(3-cyanopyridin-4-yl)ethan-1-one O-benzyloxime, 4-cyano-bis(2-pyridyl)ketone O-benzyloxime, 1-(3-cyano-1-methylpyrrolyl)ethan-1-one O-benzyloxime, and 1-(2-cyano-1-methylpyrrolyl)ethan-1-one O-benzyloxime.

6. The method of claim 4 , where the protected oxime compound containing a cyano group is a cyano O-silyloxime selected from the group consisting of cyanoformaldehyde O-trimethylsilyloxime, 2-cyanoacetaldehyde O-trimethylsilyloxime, 2-cyanopropionaldehyde O-trimethylsilyloxime, 3-cyanobutyralde

Assignees

• Bridgestone Corp

Inventors

• Luo Steven
• Dickstein Joshua S

Classifications

• C07C255/61

  containing cyano groups and nitrogen atoms being part of imino groups bound to the same carbon skeleton · CPC title

• C08F36/00 Primary

  Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds (C08F32/00 takes precedence) · CPC title

• C08C19/22

  Incorporating nitrogen atoms into the molecule · CPC title

• C08F8/30

  Introducing nitrogen atoms or nitrogen-containing groups · CPC title

• C08C3/00

  Treatment of coagulated rubber · CPC title