Synthesis, characterization, and cure reaction of methacrylate-based multifunctional monomers for dental composites

The synthesis of 2,2-bis[(4-(2-hydroxy-3-methacryloxyethoxy)phenyl]propane (BHEP) and (1-methacryloxy-3-ethoxymethacryloxy-2-hydroxy)propane (MEHP) for use as the monomer phase in dental composites are reported. The monomers were prepared by the reaction of 2-hydroxyethyl methacrylate (HEMA) with diglycidyl-ether of bisphenol A (DGEBA) and with glycidyl methacrylate (GMA), respectively. The progress of the reaction was followed by measuring the disappearance of the epoxide group peak using FTIR and the structure of the monomers was characterized by ¹H-NMR. BHEP and MEHP have lower viscosity because of the presence of long aliphatic spacer on both sides of the aromatic ring in BHEP and the absence of aromatic rings and the presence of only one hydroxyl group in each molecule of MEHP. Thermal curing of the monomers was conducted in a DSC using benzoyl peroxide as an initiator. Photopolymerization of the monomers was also conducted with the visible light using camphorquinone and N,N-dimethylaminoethyl methacrylate as the photoinitiating system. © 2007 Wiley Periodicals, Inc. J Appl Polym Sci, 2007