Synthesis and Characteristics of Dental Composites with Novel Bis-GMA Derivate as a Resin Base

Abstract

2,2-bis [4-(2-hydroxy-3-methacryloyloxypropoxy) pheny propane (Bis-GMA) and triethylene glycol dimethacrylate (TEGDMA) have been commonly used as a viscous monomer and a reactive diluent in the organic phase of dental restorative composites, respectively. The purpose of addition of TEGDMA is mainly to decrease the high viscosity of Bis-GMA caused by hydrogen bonding between hydroxyl groups. However, some adverse effects will accompany with increased amounts of the TEGDMA, such as higher values of polymerization shrinkage, which is not undesirable for the clinical application. Therefore, substituting hydroxyl groups of Bis-GMA might be an appropriate and effective way to reduce the amount of diluents and weaken the accompanied adverse effects. This work focuses on the synthesis of a novel Bis-GMA derivate, substituting acetyl groups for hydroxyl groups in Bis-GMA. The viscosity of Bis-GMA characterized with rotational rheometer was significantly decreased from 820 Pa.s to 11 Pa.s by substitution of acetyl group, leading to the low amount of TEGDMA in resin matrix. Differential Scanning Calorimeter (DSC) was used for investigating the reaction kinetics of this novel monomer with different mass ratios of TEGDMA. The results suggested that the maximum conversion of the Ac-Bis-GMA can reach 88% while the corresponding value for Bis-GMA is 75%. Dental composites were prepared from 2,2-bis [4-(2-acetyl-3-methacryloyloxypropoxy) pheny propane (Ac-Bis-GMA) or Bis-GMA resin mixtures with TEGDMA filled with 70 wt% silica co-fillers. The results presented that dental composites prepared from new resin matrixes exhibited adequate mechanical properties.