Synthesis and characterization of a novel dimethacrylate based on adamantane as possible dental resins

In this study a novel dimethacrylate based on adamantine (AB-GMA) was synthesized and proposed as possible dental monomers for dental resin mixtures. The monomer was prepared by the reaction of glycidyl methacrylate with dicarboxylic acid ester obtained from adamantanediol and maleic anhydride. The addition reaction of glycidyl methacrylate and the acidic compound was carried out in the presence of basic catalyst tetraethylammonium bromide. AB-GMA was copolymerized with TEGDMA by varying the curing conditions: monomer composition, photoinitiator concentration and light intensity. A Real-time FTIR technique was employed to monitor the double bond conversion and the rate of polymerization. The prepared polymers were also subjected to dynamic mechanical studies (DMA). AB-GMA exhibited high degree of double bond conversion (up to 77%) and its thermo-mechanical properties were better than those of the commonly known dimethacrylates. AB-GMA showed no cytotoxicity toward growth of L929 cells and had good in vitro biocompatibility. (C) 2012 Elsevier B.V. All rights reserved.