Allyl-phenoxy-cyclophosphazene compound, and production method therefor
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).
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.