Preparation of low shrinkage stress Bis-GMA free dental resin composites with a synthesized urethane dimethacrylate monomer

Abstract

A new urethane dimethacrylate TMA was synthesized through a typical urethane reaction. TMA was used to replace 1,6-bis(methacryloxy-2-ethoxycarbonyl- amino)-2,4,4- trimethylhexane (UDMA) in UDMA based composite partially or totally to prepare TMA containing composites. Critical properties of TMA containing composites were investigated. 2,2-bis[4(2-hydroxy-3-methacryloy- propyloy)phenyl]propane (Bis-GMA) based and UDMA based composites were used as references. FT-IR and ¹H-NMR confirmed the structure of TMA. All of experimental dental resin composites had the similar double bond conversion (p > 0.05). With a certain amount of TMA, TMA containing composites could have lower volumetric shrinkage (p < 0.05) and shrinkage stress (p < 0.05) than control groups. Water sorption, solubility, flexural strength and modulus of TMA containing composites were not worse than those of control groups. All of TMA containing composites and UDMA based composite had the same fracture toughness (p > 0.05), which was higher than that of Bis-GMA based composite (p < 0.05). TMA has potential as Bis-GMA substitute to prepare Bis-GMA free dental resin composites with low shrinkage stress.