Allyl-phenoxy-cyclophosphazene compound, and production method therefor

Patent metadata

Field	Value
Publication number	US-10435422-B2
Application number	US-201615575491-A
Country	US
Kind code	B2
Filing date	May 25, 2016
Priority date	May 28, 2015
Publication date	Oct 8, 2019
Grant date	Oct 8, 2019

Abstract

An object of the present invention is to provide a mixture of cyclophosphazenes suitably substituted with phenoxy having a polymerizable functional group, such as allyl, on the phenyl ring and a production method for the mixture. The invention relates to a mixture of cyclophosphazene compounds that each contain a plurality of constituent units linked to each other, each constituent unit being represented by formula (I):

wherein R 1 and R 2 are identical or different and represent C 1-4 alkyl or the like, the mixture containing cyclophosphazene compounds in which 3, 4, and 5 constituent units represented by formula (I) are linked, wherein the cyclophosphazene compound containing 3 linked constituent units is cyclophosphazene compound (I-A) with a specific structure, compound (I-A) includes cyclophosphazene compounds (I-A2) and (I-A3) having a specific structure, and compounds (I-A2) and (I-A3) are present in an amount of 80 wt % or more in total in cyclophosphazene compound (I-A).

First claim

The invention claimed is:

1. A method for producing a mixture of cyclophosphazene compounds, the method comprising
a first step of reacting a mixture comprising 13 halocyclophosphazene compounds containing, respectively, 3 to 15 constituent units linked to each other, each unit being represented by formula (III):

wherein X represents a halogen atom, with an allylphenolate compound, and
a second step of reacting the compound obtained in the first step with a phenolate compound,

wherein the allylphenolate compound is represented by formula (IV):

wherein R 3 represents a hydrogen atom or C 1-4 alkyl,
R 4 represents C 1-4 alkyl or C 1-4 alkoxy,
m represents an integer of 0 to 4,
when m represents an integer of 2 or more, the 2 or more groups R 4 may be identical or different, and
M represents an alkali metal, and
the phenolate compound is represented by formula (V):

wherein M represents an alkali metal,
R 5 represents C 1-4 alkyl, C 1-4 alkoxy, C 2-7 alkenyl, C 2-7 alkenyloxy, C 3-8 cycloalkyl, C 3-8 cycloalkoxy, nitro, or cyano,
n represents an integer of 0 to 5, and
when n represents an integer of 2 or more, the 2 or more groups R 5 may be identical or different, and
the mixture of cyclophosphazene compounds that each comprise, respectively, 3 to 15 constituent units linked to each other, each constituent unit being represented by formula (I):

wherein R 1 and R 2 are identical or different, and each represents phenyl that is optionally substituted with at least one member selected from the group consisting of C 1-4 alkyl, C 1-4 alkoxy, C 2-7 alkenyl, C 2-7 alkenyloxy, C 3-8 cycloalkyl, C 3-8 cycloalkoxy, nitro, and cyano, wherein
(1) the mixture of cyclophosphazene compounds comprises cyclophosphazene compound (I-A) represented by formula (I-A):

wherein R 1 and R 2 are as defined above,
(2) cyclophosphazene compound (I-A) comprises cyclophosphazene compound (I-A2), wherein of 3 groups R 1 and 3 groups R 2 , 2 groups are the following group (II):

wherein R 3 represents a hydrogen atom or C 1-4 alkyl,
R 4 represents C 1-4 alkyl or C 1-4 alkoxy,
m represents an integer of 0 to 4, and
when m represents an integer of 2 or more, the 2 or more groups R 4 may be identical or different, and cyclophosphazene compound (I-A3), wherein of 3 groups R 1 and 3 groups R 2 , 3 groups are group (II), and
(3) cyclophosphazene compound (I-A2) and cyclophosphazene compound (I-A3) are present in an amount of 80 wt % or more in total in cyclophosphazene compound (I-A).

2. The method for producing a mixture of cyclophosphazene compounds according to claim 1 , wherein the first step comprises step (1-1A) of adding the mixture comprising 13 halocyclophosphazene compounds to a slurry of the allylphenolate compound.

3. The method for producing a mixture of cyclophosphazene compounds according to claim 1 , wherein the first step comprises step (1-1B) of adding the allylphenolate compound to the mixture comprising 13 halocyclophosphazene compounds.

Assignees

• Otsuka Chemical Co Ltd

Inventors

• Hayashi Masatoshi
• Suzuki Daisuke

Classifications

• C08F287/00

  Macromolecular compounds obtained by polymerising monomers on to block polymers · CPC title

• C08F290/062

  Polyethers · CPC title

• C07F9/65815 Primary

  n = 3 · CPC title

• C07F9/65818

  n > 4 · CPC title

• C09K21/12 Primary

  containing phosphorus · CPC title