Synthesis of novel prepolymers containing no bisphenol A and preparation of organic matrices for dental applications

Abstract

Two kinds of novel bifunctional methacrylated prepolymers (170-2MA and 631-2MA) which have similar structure with 2,2-bis [4- (2'-hydroxy-3'-methacryloyloxypropoxy)phenyl] propane (Bis-GMA) was synthesized for dental applications as an alternative to Bis-GMA containing bisphenol A that is doubtful as an endocrine disrupter. The organic matrices were prepared by mixing a diluent and/or a monomer with the synthesized methacrylated prepolymers. The yield, viscosity, and chemical structures of the prepolymers and the physical and mechanical properties of the organic matrices were evaluated. The yields of the prepolymers synthesized through a ring-opening reaction of epoxy compound and methacrylic acid were above 90% and the viscosities of the prepolymers were much lower than that of the Bis-GMA control. From the results of H-1-NMR and FTIR analyses, the chemical structures of the prepolymers were similar to that of Bis-GMA. In addition, the curing time, polymerization shrinkage, photoconversion, polymerization depth, and compressive strength of the organic matrices formulated with 170-2MA and 631-2MA prepolymers exhibited comparable to or better than those of the existing Bis-GMA-based one. These results suggest that the novel methacrylated prepolymers which have no endocrine disrupter can be an alternative to Bis-GMA and be applicable to dental polymer materials.