Synthesis, Characterization and Photopolymerization of a New Dimethacrylate Monomer Based on (α-Methyl-benzylidene)bisphenol Used as Root Canal Sealer

Abstract

Methacrylate resin-based sealers have attracted wide attention because of their easy handling, superior aesthetic qualities, good mechanical properties and excellent adhesive ability with dentin. 2,2-Bis[4-(2′-hydroxy-3′-methacryloyloxypropoxy)-phenyl]-propane (Bis-GMA) is the main component of the newly developed commercial root canal sealer 'Epiphany', which is one of the methacrylate resin-based sealers. In order to further reduce the polymerization volume shrinkage of Bis-GMA, 4,4′-(α-methylbenzylidene)-bis(2′-hydroxy-3′-methacryloyloxy-propoxy)benzene (4,4′-AMBHMB) with higher molecular weight and larger molecular volume was synthesized to replace Bis-GMA as one of the components of the root canal sealer used in this study. The structure of monomer 4,4′-AMBHMB was confirmed by FT-IR, 1H-NMR, mass spectrum and elemental analysis. The photopolymerization behavior of mixture of 4,4′-AMBHMB and triethylene glycol dimethacrylate (TEGDMA) was investigated by FT-IR. Degree of double bond conversion, volume shrinkage, water sorption and solubility, diffusion coefficient value, flexure strength and glass transition temperature of 4,4′-AMBHMB/TEGDMA system with a mass ratio of 50:50 were measured. A 50:50 Bis-GMA/TEGDMA formulation was used as reference. The results illustrated that 4,4′-AMBHMB/TEGDMA system had the same double bond conversion and water sorption with Bis-GMA/TEGDMA system. Polymerization shrinkage, water solubility and diffusion coefficient of 4,4′-AMBHMB/TEGDMA system were lower than that of the Bis-GMA/TEGDMA system, whereas the flexural strength and glass-transition temperature of 4,4′-AMBHMB/TEGDMA system were higher than that of the Bis-GMA/TEGDMA system.