Synthesis of a liquid-crystalline resin monomer with the property of low shrinkage polymerization

Abstract

To reduce the polymerization shrinkage of the dental resin composites, a new liquid-crystalline resin monomer was developed. The acrylate liquid crystalline resin monomer (ALCRM), (4-3-(acryloyloxy)-2-hydroxypropoxy) phenyl 4-(3-(acryloyloxy)-2-hydroxypropoxy) benzoate, was synthesized by a three-step method. Using the ALCRM as the main monomer, the degree of conversion (DC) and the volume shrinkage of the resin matrix were compared with the traditional composite resin monomer (Bis-GMA), 2,2-bis[4-(2-hydroxy-3-methacryloyloxy-propoxy)-phenyl] propane. The new monomer showed liquid crystalline characteristics with a mesomorphic phase- transition temperature between 18°C and 42°C. When copolymerized with triethylene glycol dimethacrylate (TEGDMA) at a weight ratio of 7:3, the DC of ALCRM was higher and the volume shrinkage was 3.62±0.26%, which was less than that of the Bis-GMA. The ALCRM exhibits promising potential for the development of superior dental resins with low volume shrinkage.