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Synthesis and photopolymerizations of new phosphonated monomers for dental applications



Three novel phosphonated methacrylate monomers have been synthesized and studied for use in dental applications. Two of the monomers were synthesized from the reactions of glycidyl methacrylate (GMA) with (diethoxy-phosphoryl)-acetic acid (monomer 1) and (2-hydroxy-ethyl)-phosphonic acid dimethyl ester (monomer 2). These monomers showed high crosslinking tendencies during thermal bulk and solution polymerizations. The third monomer (monomer 3) was prepared by the reaction of bisphenol A diglycidylether (DER) with (diethoxy-phosphoryl)-acetic acid and subsequent conversion of the resulting diol to the methacrylate with methacryloyl chloride. The homopolymerization and copolymerization behaviors of the synthesized monomers were also investigated with glycerol dimethacrylate (GDMA), triethylene glycol dimethacrylate (TEGDMA), and 2,2-bis[4-(2-hydroxy-3-methacryloyloxy propyloxy) phenyl] propane (bis-GMA) using photodifferential scanning calorimetry at 40 °C using 2,2′-dimethoxy-2-phenyl acetophenone (DMPA) as photoinitiator. Monomer 1 showed polymerization rate similar or greater than dimethacrylates studied here but with higher conversion. The maximum rate of polymerizations decreased in the following order: 1∼TEGDMA>GDMA∼bis-GMA∼3>2. A synergistic effect in the rate of polymerization was observed during copolymerizations. © 2008 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 46: 2290–2299, 2008