Objectives: The currently available commercial dental resin composites have limitations in use owing to the high viscosity and water sorption of Bisphenol A glycidyl methacrylate (BisGMA). The objective of this study was to obtain a BisGMA analog with reduced viscosity and hydrophilicity for potential use as an alternative to BisGMA in dental resin composites.
Methods: The targeted chlorinated BisGMA (Cl-BisGMA) monomer was synthesized via the Appel reaction. The structural modification was confirmed via H- and C nuclear magnetic resonance spectroscopy, Fourier transform infrared spectroscopy, and mass spectrometry. Five resin mixtures (70:30wt.%: F1=BisGMA/TEGDMA; F2=Cl-BisGMA/TEGDMA; F3=Cl-BisGMA only; F4=Cl-BisGMA/BisGMA; F5 contained 15% TEGDMA with equal amounts of BisGMA and Cl-BisGMA) were prepared. The viscosity, degree of double-bond conversion (DC), water sorption (W), and solubility (W) were tested. Cell viability and live/dead assays, as well as cell attachment and morphology assessments, were applied for cytotoxicity evaluation.
Results: Cl-BisGMA was successfully synthesized with the viscosity reduced to 7.22 (Pas) compared to BisGMA (909.93,Pas). Interestingly, the DC of the F2 resin was the highest (70.6%). By the addition of equivalence concentration of Cl-BisGMA instead of BisGMA, the W was decreased from 2.95% (F1) to 0.41% (F2) with no significant change in W. However, the W increased with high Cl-BisGMA content. Biological tests revealed that all the resins were biocompatible during CL1 incubation.
Significance: The experimental resins based on Cl-BisGMA exhibited improved properties compared with the control samples, e.g., biocompatibility and lower viscosity, indicating that Cl-BisGMA can be considered as a potential monomer for application in dental resin composites.
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| http://dx.doi.org/10.1016/j.dental.2019.07.013 | DOI Listing |
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