Bis(benzoxazinyl)phthalimidine and associated curable composition and composite
A bis(benzoxazinyl)phthalimidine has the structure wherein R 1 , R 2 , R 3 , R 4 , j, and k are defined herein. The bis(benzoxazinyl)phthalimidine is useful as a component of a curable composition. It exhibits a high melting temperature and a high exotherm onset temperature. Also described is a composite that includes a reinforcing filler and the curing product of the bis(benzoxazinyl)phthalimidine.
1. A bis(benzoxazinyl)phthalimidine having the structure
wherein
R 1 is hydrogen, C 1 -C 6 alkyl, phenyl, or phenyl substituted with up to five substituents independently selected from halogen and C 1 -C 6 alkyl;
each occurrence of R 2 is independently selected from the group consisting of unsubstituted or substituted C 1 -C 30 hydrocarbyl;
each occurrence of R 3 is independently C 1 -C 6 alkyl;
j is 0, 1, 2, 3, or 4;
each occurrence of R 4 is independently selected from the group consisting of C 1 -C 12 alkyl, C 2 -C 12 alkenyl, and C 1 -C 12 alkoxyl; and
each occurrence of k is independently 0, 1, 2, or 3.
2. The bis(benzoxazinyl)phthalimidine of claim 1 , wherein R 1 is phenyl, or phenyl substituted with 1, 2, 3, 4, or 5 substituents independently selected from halogen and C 1 -C 6 alkyl.
3. The bis(benzoxazinyl)phthalimidine of claim 1 , wherein R 1 is phenyl.
4. The bis(benzoxazinyl)phthalimidine of claim 1 , wherein each occurrence of R 2 is independently selected from the group consisting of C 1 -C 12 alkyl, anthracenyl, biphenyl, cyclohexenyl, cyclopentenyl, indanyl, naphthyl, and phenyl.
5. The bis(benzoxazinyl)phthalimidine of claim 1 , wherein each occurrence of R 2 is C 1 -C 12 alkyl or phenyl.
6. The bis(benzoxazinyl)phthalimidine of claim 1 , wherein j is 0, and each occurrence of k is 0.
7. The bis(benzoxazinyl)phthalimidine of claim 1 , wherein R 1 is phenyl, each occurrence of R 2 is phenyl, j is 0, and each occurrence of k is 0.
8. A curable composition comprising the bis(benzoxazinyl)phthalimidine of claim 1 .
9. The curable composition of claim 8 , further comprising an epoxy resin selected from the group consisting of aliphatic epoxy resins, cycloaliphatic epoxy resins, aromatic epoxy resins, dicyclopentadiene-type (DCPD-type) epoxy resins, and combinations thereof.
10. The curable composition of claim 9 , wherein the epoxy resin is selected from the group consisting of bisphenol-A diglycidyl ether, bisphenol-F diglycidyl ether, neopentylglycol diglycidyl ether, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexane carboxylate, N,N-diglycidyl-4-glycidyloxyaniline, N,N,N′,N′-tetraglycidyl-4,4′-diaminodiphenylmethane, 2-phenyl-3,3-bis(4-glycidyloxyphenyl)phthalimidine, and combinations thereof.
11. The curable composition of claim 9 , wherein the epoxy resin is a diglycidyl ether compound having the structure
wherein
R 1 is hydrogen, C 1 -C 6 alkyl, phenyl, or phenyl substituted with up to five substituents independently selected from halogen and C 1 -C 6 alkyl;
each occurrence of R 3 is independently C 1 -C 6 alkyl;
j is 0, 1, 2, 3, or 4;
each occurrence of R 4 is independently selected from the group consisting of C 1 -C 12 alkyl, C 2 -C 12 alkenyl, and C 1 -C 12 alkoxyl; and
each occurrence of m is independently 0, 1, 2, 3, or 4.
12. The curable composition of claim 7 , comprising the bis(benzoxazinyl)phthalimidine of claim 7 .
13. A composite comprising a reinforcing filler and a curing product of the bis(benzoxazinyl)phthalimidine of claim 1 .
14. The composite of claim 13 , comprising a reinforcing filler and a curing product of the bis(benzoxazinyl)phthalimidine of claim 7 .