Synthesis, characterization, and curing of a new acrylate-based dental restorative resin

The synthesis of monomer1.3-bis[(2-hydroxy-3-acrylate) proppyloxy]2-hydroxy propane (BHAPP) is reported for the possible use in dental restoratives. The monomer was prepared by the reaction of acrylic acid with diglycerol diglycidyl ether (DGE) in the presence of triethyl amine as a catalyst. The progress of the reaction at 60 C followed by measuring the intensity of the epoxide absorption peak at 915 cm, which has reached to its minimum value after 5 h. The structure of the monomer was characterized by FTIR and 1H-NMR. The monomer was a moderately viscous light yellow color liquid having a refractive index of 1.544. Thermal curing of the monomer is DSC in the presence of benzoyl peroxide showed exothermic peak with maximum temeperature (Tp) varied from 89 to 107 C depending on the heating rate and activation energy of 83 kJ/mol. Photopolymerization of the monomer by visible light in the presence of camphorquinone and N,N-dimehtylaminoethyl methacrylate as the photoinitiating system showed maximum 60% conversion after 40 s exposure. (c) 2008 Wiley Periodicals, Inc.