A Low-Viscosity BisGMA Derivative for Resin Composites: Synthesis, Characterization, and Evaluation of Its Rheological Properties

Abstract

This study aimed to synthesize new bisphenol A-glycidyl methacrylate (BisGMA) derivatives, targeting a reduction in its viscosity by substituting one of its OH groups, the leading cause of its high viscosity, with a chlorine atom. Hence, this monochloro-BisGMA (mCl-BisGMA) monomer was synthesized by Appel reaction procedure, and its structure was confirmed using Fourier transform infrared spectroscopy, 1H and 13C-nuclear magnetic resonance spectroscopy, and mass spectroscopy. The viscosity of mCl-BisGMA (8.3 Pa·s) was measured under rheometry conditions, and it was found to be more than 65-fold lower than that of BisGMA (566.1 Pa·s) at 25 °C. For the assessment of the viscosity changes of model resins in the presence of mCl-BisGMA, a series of resin matrices, in which, besides BisGMA, 50 wt % was triethylene glycol dimethacrylate, were prepared and evaluated at 20, 25, and 35 °C. Thus, BisGMA was incrementally replaced by 25% mCl-BisGMA to obtain TBC0, TBC25, TBC50, TBC75, and TBC100 blends. The viscosity decreased with temperature, and the mCl-BisGMA content in the resin mixture increased. The substantial reduction in the viscosity value of mCl-BisGMA compared with that of BisGMA may imply its potential use as a dental resin matrix, either alone or in combination with traditional monomers. However, the various properties of mCl-BisGMA-containing matrices should be evaluated.