C-M Chung1, J-G Kim, M-S Kim, K-M Kim, K-N Kim. 1. Department of Chemistry, Yonsei University, Wonju, Kangwon-do 220-710, South Korea. cmchung@dragon.yonsei.ac.kr
Abstract
OBJECTIVE: This study was conducted to evaluate the potential of a novel trifunctional methacrylate as a component of a photocurable composite resin with reduced curing shrinkage. METHODS: Tris[4-(2'-hydroxy-3'-methacryloyloxypropoxy)phenyl]methane (TTEMA) was synthesized by reacting triphenylolmethane triglycidyl ether (TTE) with methacrylic acid in the presence of 4-(dimethylamino)pyridine. Photopolymerization reactivity and volumetric shrinkage of unfilled resins based on TTEMA were investigated by Fourier transform infrared spectroscopy and density measurements, respectively, and the results were compared with those for conventional dental monomers. A three-point bending test of the TTEMA-containing composite resin was carried out. RESULTS: TTEMA was easily prepared in a good yield of 89%. Unfilled resins of TTEMA and bis-GMA, each containing 40% TEGDMA, showed similar photopolymerization reactivity. TTEMA exhibited a very low photopolymerization shrinkage of 2.09%, and 3:2 TTEMA-TEGDMA unfilled resin revealed 10% lower shrinkage than a conventional bis-GMA system containing the same amount of TEGDMA. The flexural strength of a light-activated composite resin formulated with TTEMA is comparable to that of a bis-GMA composite resin under the same conditions. SIGNIFICANCE: TTEMA is promising for application as a photocurable dental monomer due to ease of synthesis, good polymerization reactivity, and relatively low curing shrinkage.
OBJECTIVE: This study was conducted to evaluate the potential of a novel trifunctional methacrylate as a component of a photocurable composite resin with reduced curing shrinkage. METHODS:Tris[4-(2'-hydroxy-3'-methacryloyloxypropoxy)phenyl]methane (TTEMA) was synthesized by reacting triphenylolmethane triglycidyl ether (TTE) with methacrylic acid in the presence of 4-(dimethylamino)pyridine. Photopolymerization reactivity and volumetric shrinkage of unfilled resins based on TTEMA were investigated by Fourier transform infrared spectroscopy and density measurements, respectively, and the results were compared with those for conventional dental monomers. A three-point bending test of the TTEMA-containing composite resin was carried out. RESULTS:TTEMA was easily prepared in a good yield of 89%. Unfilled resins of TTEMA and bis-GMA, each containing 40% TEGDMA, showed similar photopolymerization reactivity. TTEMA exhibited a very low photopolymerization shrinkage of 2.09%, and 3:2 TTEMA-TEGDMA unfilled resin revealed 10% lower shrinkage than a conventional bis-GMA system containing the same amount of TEGDMA. The flexural strength of a light-activated composite resin formulated with TTEMA is comparable to that of a bis-GMA composite resin under the same conditions. SIGNIFICANCE: TTEMA is promising for application as a photocurable dental monomer due to ease of synthesis, good polymerization reactivity, and relatively low curing shrinkage.