Photopolymerizable bisallylcarbonate and bisacrylic monomers useful in the formulation of dental composite resins and in the crosslinking of methyl methacrylate

Two new bisallylic monomers [allyl p-allyl carbonate benzoate (ApACBz) and 1,4-phenylenbis(methylene) diallyl carbonate (1,4-FMDAC)] and one bisacrylic monomer [1,4-bis(acryloyloxymethyl)benzene (1,4-BAMB)] were synthesized and used as cross-linking agents of methyl methacrylate (MMA) at different mass ratios (10, 20, 40, and 50%). All of the obtained copolymers showed improved thermal stability in comparison with that of the MMA homopolymer. Also, ApACBz and 1,4-FMDAC were used as bisphenol A glycidyl methacrylate (Bis-GMA) eluents to prepare dental resin composites. When compared to the control, the Bis-GMA-new eluent composites had a higher double-bond conversion, a higher solubility (p<0.05) and a lower flexural strength (p<0.05), whereas the elastic modulus and water sorption values were not statistically different (p>0.05). The 1,4-FMDAC and ApACBz monomers are promising eluents of Bis-GMA for the preparation of dental composites with high degrees of conversion. In addition, the ApACBz, 1,4-FMDAC, and 1,4-BAMB monomers are potentially useful crosslinking agents when polymer networks of poly(methyl methacrylate) with a high thermal stability are desired. The application-oriented tests of the monomers in dental composite formulations showed a sufficient storage stability, high photocuring activity, excellent crosslinking of MMA, and good thermal and mechanical properties.(C) 2015 Wiley Periodicals, Inc.