Bondable microcapsules and surface functionalized fillers

1. A composition comprising a monomer, an initiator, and a nonbiodegradable microcapsule encapsulating an aqueous solution of a salt wherein said microcapsule has a surface functionalized with a polymerizable methacrylate functional group capable of polymerizing with said monomer by covalently bonding the polymerizable acrylate functional group with the monomer.

2. The composition of claim 1 wherein the aqueous solution of a salt contains ions selected from the group consisting of: fluoride, calcium, phosphate, and combinations thereof.

3. The composition of claim 1 comprising a combination of salt ions wherein the combination of salt ions is achieved by using a plurality of microcapsules that contain either fluoride ions, calcium ions, or phosphate ions, wherein each microcapsule contains only one of the fluoride ions, calcium ions, or phosphate ions.

4. The composition of claim 1 wherein the aqueous solution of a salt contains benzalkonium ions or cetylpyridinium ions.

5. The composition of claim 1 wherein the aqueous solution of a salt is specifically a combination of salts that result in a buffered solution.

6. The composition of claim 5 wherein the buffered solution contains a therapeutic agent.

7. The composition of claim 1 further comprising a photoinitiator.

8. A composition comprising a polymeric continuous phase and a discontinuous phase wherein the continuous phase comprises a polymeric material and the discontinuous phase comprised a microcapsule encapsulating an aqueous solution, wherein said microcapsule has a surface functionalized with a polymerizable methacrylate functional group and is covalently bonded to the polymeric continuous phase.

9. The composition of claim 8 wherein the aqueous solution is an aqueous solution of a salt that contains ions selected from the group consisting of: fluoride, calcium, phosphate, and combinations thereof.

10. The composition of claim 8 wherein the aqueous solution is an aqueous buffered therapeutic solution comprising benzalkonium ions, cetylpyridinium ions, or combinations thereof.

11. The composition of claim 8 comprising a plurality of microcapsules that contain either fluoride ions, calcium ions, phosphate ions, benzalkonium ions, cetylpyridinium ions, or iodide ions wherein each microcapsule contains only one of the ions.

12. The composition of claim 8 wherein said aqueous solution comprises a silicone or rubber-based material.

13. The composition of claim 8 wherein said polymeric continuous phase comprises at least one monomer and a photoinitiator in the continuous phase and a microcapsule and an inhibitor in the discontinuous phase and wherein a light source activates the photoinitiator, which allows the monomers in the continuous phase to polymerize and bind with the acrylate functional group on the microcapsule.

14. The composition of claim 13 wherein the at least one monomer comprises TEGDMA and bisGMA monomers.

15. The composition of claim 14 wherein the microcapsule is between 2% w/w and 5% w/w of the composition and wherein said acrylate functional group is a methacrylate functional group on the surface, and wherein the methacrylate functional group is capable of reacting with a methacrylate group positioned on the TEGDMA and bisGMA monomers in the continuous phase.

16. A method for manufacturing a composition having a microcapsule and a continuous phase wherein said microcapsule comprises a methacrylate functionalized surface capable of covalently bonding to the continuous phase comprising:

a. mixing an oligomeric urethane by reaction of a diol and diisocyanate, in which the diisocyanate is used in molar excess, and reacting for about 1 hour;

b. adding 2-hydroxyethylmethacrylate to the oligomeric urethane mixture to terminate chain ends with methacrylate functional groups to create a functionalized urethane;

c. isolating the functionalized urethane;

d. adding the isolated functionalized urethane to an oil phase comprising an emulsifying agent and an organic solvent wherein a surfactant free inverse emulsion is formed with addition of an aqueous phase that may contain a salt;

e. adding diol to the surfactant free inverse emulsion to polymerize the urethane oligomers and encapsulate the aqueous phase; and

f. isolating the microcapsules by centrifugation.

17. The method of claim 16 wherein the continuous phase comprises monomers selected from the group consisting of: TEGDMA, bisGMA, and combinations thereof.

18. The method of claim 16 wherein the aqueous phase comprises fluoride ions, calcium ions, phosphate ions, benzalkonium ions, cetylpyridinium ions, iodide ions, or combinations thereof.

19. The method of claim 16 wherein the aqueous phase comprises a silicone or rubber-based material.