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 mixture of cyclophosphazene compounds that each comprise 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 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,
the mixture comprising 3 cyclophosphazene compounds containing, respectively, 3, 4, and 5 constituent units represented by formula (I) linked to each other
wherein
(1) the cyclophosphazene compound in which 3 constituent units represented by formula (I) are linked to each other is 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 mixture of cyclophosphazene compounds according to claim 1 , which has an acid value of 0.5 mgKOH/g or less.
3. A mixture of 13 cyclophosphazene compounds containing, 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).
4. The mixture of cyclophosphazene compounds according to claim 3 , wherein cyclophosphazene compound (I-A2) and cyclophosphazene compound (I-A3) are present in an amount of 85 wt % or more in total in cyclophosphazene compound (I-A).
5. The mixture of cyclophosphazene compounds according to claim 3 , wherein
(1) the mixture of cyclophosphazene compounds comprises cyclophosphazene compound (I-B) represented by formula (I-B):
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 3-9 cycloalkyl, C 3-8 cycloalkoxy, nitro, and cyano,
(2) cyclophosphazene compound (I-B) comprises
cyclophosphazene compound (I-B3), wherein of 4 groups R 1 and 4 groups R 2 , 3 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,
cyclophosphazene compound (I-B4), wherein of 4 groups R 1 and 4 groups R 2 , 4 groups are allylphenyl represented by group (II), and
cyclophosphazene compound (I-B5), wherein of 4 groups R 1 and 4 groups R 2 , 5 groups are allylphenyl represented by group (II), and
(3) cyclophosphazene compound (I-B3), cyclophosphazene compound (I-B4), and cyclophosphazene compound (I-B5) are present in an amount of 80 wt % or more in total in cyclophosphazene compound (I-B).
6. The mixture of cyclophosphazene compounds according to claim 3 , which has an acid value of 0.5 mgKOH/g or less.
7. A flame retardant comprising the mixture of cyclophosphazene compounds according to claim 1 .
8. A flame-retardant resin composition comprising the mixture of cyclophosphazene compounds according to claim 1 and a resin.
9. The flame-retardant resin composition according to claim 8 , wherein the mixture of cyclophosphazene compounds is present in an amount of 0.1 to 100 parts by weight per 100 parts by weight of the resin.
10. A molded article obtained by molding the flame-retardant resin composition according to claim 8 .
11. A thermosetting resin composition comprising the mixture of cyclophosphazene compounds according to claim 1 and a dienophile compound.
12. A molded article obtained by molding the thermosetting resin composition according to claim 11 .
13. A low-dielectric circuit board material obtained from the thermosetting resin composition according to claim 11 .
14. A flame retardant comprising the mixture of cyclophosphazene compounds according to claim 3 .
15. A flame-retardant resin composition comprising the mixture of cyclophosphazene compounds according to claim 3 and a resin.
16. The flame-retardant resin composition according to claim 15 , wherein the mixture of cyclophosphazene compounds is present in an amount of 0.1 to 100 parts by weight per 100 parts by weight of the resin.
17. A molded article obtained by molding the flame-retardant resin composition according to claim 15 .
18. A thermosetting resin composition comprising the mixture of cyclophosphazene compounds according to claim 3 and a dienophile compound.
19. A molded article obtained by molding the thermosetting resin composition according to claim 18 .
20. A low-dielectric circuit board material obtained from the thermosetting resin composition according to claim 18 .