Hydroxyapatite grafted fumarate based macromers for biodegradable composites
View Patent ↗A composition is disclosed which comprises (i) a macromer prepared by reacting an unsaturated diacid having a carbon-carbon double bond and a saturated diacid, and (ii) a bioactive ceramic grafted to the macromer. In one embodiment, the unsaturated diacid having a carbon-carbon double bond is fumaric acid, the saturated diacid is compatible with fumaric acid and poly(propylene fumarate) such as succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid and mixtures thereof, and the bioactive ceramic is hydroxyapatite. In another embodiment, hydroxyapatite is grafted with a biodegradable and crosslinkable macromer comprising silane units alternating with furnarate and adipate units.
1. A composition comprising:
a macromer prepared by reacting an unsaturated diacid having a carbon-carbon double bond and a saturated diacid, wherein the unsaturated diacid having a carbon-carbon double bond is fumaric acid; and
a bioactive ceramic grafted to the macromer, wherein the bioactive ceramic is hydroxyapatite grafted to the macromer by way of silicate groups.
2. A biodegradable composite comprising:
(a) a polymeric matrix; and
(b) the composition of claim 1 crosslinked to the matrix.
3. The composite of claim 2 wherein:
the matrix has a carbon-carbon double bond.
4. The composite of claim 3 wherein:
the matrix comprises poly(propylene fumarate).
5. The composite of claim 2 wherein:
the composite is suitable as a scaffold for tissue regeneration.
6. The composite of claim 5 wherein:
the tissue is bone.
7. A crosslinkable, biodegradable material comprising:
a polymer having a carbon-carbon double bond;
the composition of claim 1 , and
a crosslinking agent for crosslinking the polymer and the composition.
8. The material of claim 7 wherein:
the polymer comprises poly(propylene fumarate).
9. The material of claim 8 wherein:
the crosslinking agent is a free radical initiator.
10. The composition of claim 1 wherein:
the saturated diacid is selected from diacids compatible with fumaric acid and poly(propylene fumarate).
11. The composition of claim 10 wherein:
the saturated diacid is selected from succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid and mixtures thereof.
12. A composition comprising:
a macromer prepared by reacting an unsaturated diacid having a carbon-carbon double bond, a saturated diacid and a silane coupling agent; and
a bioactive ceramic grafted to the macromer.
13. The composition of claim 12 wherein:
the unsaturated diacid having a carbon-carbon double bond is fumaric acid, the saturated diacid is selected from diacids compatible with fumaric acid and poly(propylene fumarate), and the silane coupling agent is a dihalodialkylsilane.
14. The composition of claim 13 wherein:
the saturated diacid is selected from succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid and mixtures thereof.
15. The composition of claim 12 wherein:
the macromer is prepared by reacting the unsaturated diacid having a carbon-carbon double bond, the saturated diacid, the silane coupling agent, and an ester of the saturated diacid.
16. The composition of claim 15 wherein:
the saturated diacid is adipic acid,
the silane coupling agent is a dichlorodimethylsilane, and
the ester is a monomethyl ester of adipic acid.
17. The composition of claim 15 wherein:
the bioactive ceramic comprises hydroxyapatite particles having a particle size of less than 10,000 nanometers.
18. A composition comprising:
a macromer including silane units, units derived from an unsaturated diacid having a carbon-carbon double bond, and units derived from a saturated diacid; and
a bioactive ceramic grafted to the macromer.
19. The composition of claim 18 wherein:
the macromer includes silane units, fumarate units, and units derived from a saturated diacid, and
the bioactive ceramic is hydroxyapatite.
20. The composition of claim 18 wherein:
the macromer includes silane units, fumarate units, and adipate units, and the bioactive ceramic is hydroxyapatite.
21. The composition of claim 18 wherein:
the bioactive ceramic is hydroxyapatite.
22. The composition of claim 21 wherein:
the hydroxyapatite is grafted to the macromer by way of silicate groups.