Evaluation of monomers derived from resorcinol as eluents of bisphenol A glycidyl dimethacrylate for the formulation of dental composite resins

Abstract

ABSTRACTThe objective of this work was to synthesize two bio‐based monomers, using the resorcinol as raw material, and its effect as bisphenol A glycidyl dimethacrylate (Bis‐GMA) eluents on different chemical–physical and biological properties of experimental photopolymerizable composite resins. The acrylic 1,3‐phenylen diacrylic (1,3‐FDA) and methacrylic 1,3‐phenylen dimethacrylic (1,3‐FDMA) monomers were synthesized and fully characterized through FTIR and 1H‐NMR spectroscopies. Experimental photopolimerizable composites were formulated using Bis‐GMA/1,3‐FDA or Bis‐GMA/1,3‐FDMA as organic matrix. The materials were compared with a Bis‐GMA/TEGDMA resin‐based composite used as control. Polymerization kinetics was evaluated by means of FTIR spectroscopy. Polymerization stress was directly measured through a polymerization stress tester. The cell viability of the composites was evaluated using the MTT assay. One‐way analysis of variance and Tukey's test were used for statistical analysis. The materials formulated with the 1,3‐FDA monomer showed higher Rpmax values and lower polymerization stress values (p < 0.05), while the flexural strength, water sorption, and solubility remained similar to the TEGDMA composite. Conversely, the materials formulated with the 1,3‐FDMA monomer showed a lower degree of conversion and statistically lower flexural strength (p < 0.05). All materials exhibited a cellular viability close to 100%. Concerning the study conditions, the acrylic 1,3‐FDA monomer could be considered an alternative to TEGDMA in the formulation of photopolymerizable dental composite resins. © 2019 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2020, 137, 48576.