Polymerizable 4,4′-spirobi[chromane]-2,2′-diones and curable compositions including the same
A polymerizable compound is represented by the formula (I). Each R 1 independently represents a monovalent group having from 3 to 12 carbon atoms that comprises at least one of an epoxy group, an acryl group, or a methacryl group. Each R 2 independently represents H, F, Cl, Br, C 1 -C 12 alkyl, C 2 -C 3 carbonylalkyl, or C 2 -C 5 carboalkoxy. Each R 3 independently represents H, F, Cl, Br, C 1 -C 12 alkyl, C 2 -C 3 carbonylalkyl, or C 2 -C 5 carboalkoxy. Each n is independently 0, 1, 2, 3, or 4. Curable compositions including the polymerizable compound are also disclosed.
1. A polymerizable compound represented by the formula
wherein
each R 1 independently represents a monovalent group having from 3 to 12 carbon atoms that comprises at least one of an epoxy group, an acryl group, or a methacryl group;
each R 2 independently represents H, F, Cl, Br, C 1 -C 12 alkyl, C 2 -C 3 carbonylalkyl, or C 2 -C 5 carboalkoxy;
each R 3 independently represents H, F, Cl, Br, C 1 -C 12 alkyl, C 2 -C 3 carbonylalkyl, or C 2 -C 5 carboalkoxy; and
each n is independently 0, 1, 2, 3, or 4.
2. The polymerizable compound of claim 1 , wherein at least one of R 2 and R 3 is chlorine or bromine.
3. The polymerizable compound of claim 1 , wherein each n is 0 or 1.
4. The polymerizable compound of claim 1 , wherein at least one R 1 is represented by
wherein R 4 is H or methyl, wherein x is 1 or 2.
5. The polymerizable compound of claim 1 , wherein at least one R 1 is represented by
wherein R 4 is H or methyl.
6. The polymerizable compound of claim 1 , wherein at least one R 1 is represented by
wherein R 4 is H or methyl.
7. The polymerizable compound of claim 1 , wherein at least one R 1 is represented by
wherein R 4 is H or methyl.
8. The polymerizable compound of claim 1 , wherein both R 3 are H.
9. The polymerizable compound of claim 1 , wherein at least one R 3 is OH.
10. The polymerizable compound of claim 1 , wherein at least one R 3 is C 1 -C 6 alkyl.
11. A curable composition comprising:
a polymerizable compound according to claim 1 ; and
a free radical initiator.
12. The curable composition of claim 11 , wherein the free radical initiator comprises a free radical photoinitiator.
13. The curable composition of claim 11 , further comprising free radically polymerizable monomer.
14. The curable composition of claim 11 , further comprising filler.
15. The polymerizable compound of claim 1 , wherein at least one R 1 comprises an epoxy group.
16. The polymerizable compound of claim 1 , wherein at least one R 1 comprises a glycidyl group.
17. A curable composition comprising:
a polymerizable compound according to claim 15 ; and
a curative for the polymerizable compound.
18. The curable composition of claim 17 , further comprising additional epoxy monomer.
19. The curable composition of claim 17 , further comprising filler.
20. The curable composition of claim 11 , wherein the curable composition is a curable dental restorative composition.