Radical polymerization initiator and method for producing polymers

Patent metadata

Field	Value
Publication number	US-10689336-B2
Application number	US-201916439109-A
Country	US
Kind code	B2
Filing date	Jun 12, 2019
Priority date	Nov 27, 2013
Publication date	Jun 23, 2020
Grant date	Jun 23, 2020

Abstract

The present invention involves a radical polymerization initiator comprising an organotellurium compound represented by a formula (1), wherein R 1 represents an alkyl group or the like, each of R 2 and R 3 independently represents a hydrogen atom or the like, and each of R 4 , R 5 , and R 6 independently represents a hydrogen atom or the like. The present invention provides: a radical polymerization initiator that is useful for producing a polymer that includes a double bond at the molecular terminal; and a method for producing a polymer that utilizes the radical polymerization initiator.

First claim

The invention claimed is:

1. A method for producing a polymer comprising subjecting a radically polymerizable monomer to radical polymerization in a state in which a radical polymerization initiator is present in a polymerization system,
wherein the radical polymerization initiator is an organotellurium compound represented by the following formula (1),

wherein R 1 represents a group selected from:
an alkyl group having 1 to 10 carbon atoms;
a cycloalkyl group having 3 to 10 carbon atoms which is unsubstituted, or substituted with a substituent selected from a halogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an amino group, a nitro group, a cyano group, and —CORa (wherein Ra represents an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, or a haloalkyl group having 1 to 8 carbon atoms);
an aryl group having 6 to 20 carbon atoms which is unsubstituted, or substituted with a substituent selected from a halogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an amino group, a nitro group, a cyano group, and —CORa (wherein Ra represents an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, or a haloalkyl group having 1 to 8 carbon atoms); and
an aromatic heterocyclic group which is unsubstituted, or substituted with a substituent selected from a halogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an amino group, a nitro group, a cyano group, and —CORa (wherein Ra represents an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, an aryl group having 6 to 20 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, or a haloalkyl group having 1 to 8 carbon atoms),
each of R 2 and R 3 independently represents a group selected from:
a hydrogen atom;
an aliphatic hydrocarbon group having 1 to 10 carbon atoms;
an aryl group having 6 to 20 carbon atoms which is unsubstituted, or substituted with a substituent selected from a halogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an amino group, a nitro group, a cyano group, and —CORa (wherein Ra represents an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, or a haloalkyl group having 1 to 8 carbon atoms);
an aromatic heterocyclic group which is unsubstituted, or substituted with a substituent selected from a halogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an amino group, a nitro group, a cyano group, and —CORa (wherein Ra represents an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an aryloxy group having 6 to 10 carbon atoms or a haloalkyl group having 1 to 8 carbon atoms);
a halogen atom;
a carboxyl group;
a hydrocarbyl oxycarbonyl group having 2 to 10 carbon atoms;
a cyano group; and
an amide group,
and each of R 4 , R 5 and R 6 independently represents a group selected from:
a hydrogen atom;
an aliphatic hydrocarbon group having 1 to 10 carbon atoms;
an aryl group having 6 to 20 carbon atoms which is unsubstituted, or substituted with a substituent selected from a halogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an amino group, a nitro group, a cyano group, and —CORa (wherein Ra represents an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, or a haloalkyl group having 1 to 8 carbon atoms);
an aromatic heterocyclic group which is unsubstituted, or substituted with a substituent selected from a halogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an amino group, a nitro group, a cyano group, and —CORa (wherein Ra represents an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, or a haloalkyl group having 1 to 8 carbon atoms);
a halogen atom;
a carboxyl group;
a hydrocarbyl oxycarbonyl group having 2 to 10 carbon atoms;
a cyano group; and
an amide group, and
a group represented by the following formula (2),
wherein 2 groups selected from R 2 to R 6 may bond together to form a ring other than an aromatic ring,

wherein R 7 represents a group selected from:
an alkyl group having 1 to 10 carbon atoms;
a cycloalkyl group having 3 to 10 carbon atoms which is unsubstituted, or substituted with a substituent selected from a halogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an amino group, a nitro group, a cyano group, and —CORa (wherein Ra represents an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, or a haloalkyl group having 1 to 8 carbon atoms);
an aryl group having 6 to 20 carbon atoms which is unsubstituted, or substituted with a substituent selected from a halogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an amino group, a nitro group, a cyano group, and —CORa (wherein Ra represents an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, or a haloalkyl group having 1 to 8 carbon atoms); and
an aromatic heterocyclic group which is unsubstituted, or substituted with a substituent selected from a halogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an amino group, a nitro group, a cyano group, and —CORa (wherein Ra represents an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, an aryl group having 6 to 20 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, or a haloalkyl group having 1 to 8 carbon atoms),
and each of R 8 and R 9 independently represents a group selected from:
a hydrogen atom;
an aliphatic hydrocarbon group having 1 to 10 carbon atoms;
an aryl group having 6 to 20 carbon atoms which is unsubstituted, or substituted with a substituent selected from a halogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an amino group, a nitro group, a cyano group, and —CORa (wherein Ra represents an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, or a haloalkyl group having 1 to 8 ca

Assignees

• Univ Kyoto
• Zeon Corp

Inventors

• Bando Fumiaki
• Yamago Shigeru

Classifications

• C08F212/08

  Styrene · CPC title

• C07C395/00 Primary

  Compounds containing tellurium · CPC title

• C08F236/08

  Isoprene · CPC title

• C08F4/00

  Polymerisation catalysts · CPC title

• C08F2/48

  by ultraviolet or visible light · CPC title