Synthesis of Novel Monomer with Excellent Visible-Light Polymerization Ability and its Application to Dental Field

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To improve mecchanical strength under the hygroscopic condition of light-cured acrylate resins, a new monomer having both acryloyl and methacryloyl groups in one molecule, Triethyl-Ene-Glycol Acrylate-Meth-Acrylate (TEGAMA) was synthesized. Photopolymerization ability and mechanical properity (compressive strength) of TEGAMA were compared with dimethacrylate (TEGDMA) and diacrylate (TEGDA) of triethylenglycol. Photocurable monomers containing 0.5 wt% of comphorquinone and ethyl N, N-dimethylaminobenzoate as photoinitiators were irradiated with visible light (lambda>400 nm). When photo irradiation was carried out for the 30 seconds, both the amount of residual monomers and unreacted double bonds in the side chain were higher than these of TEGDMA resin. But ever since the 60 seconds irradiation, these values of TEGAMA resins were smaller than these of TEGDMA resins. The amount of residual acryloyl groups in the side chain of TEGAMA resins higher than that of methacryloyl groups throughout photoirradiation. From above mentioned results, photopolymerization mechanism of TEGAMA could be presumed that methacryloyl groups reacted with each others in some extent and after that, futhermore high cross-linking reaction was proceeded due to the residual acrylate groups in the side chain with higher reactivity more than methacryloyl groups. Amount of water adsorbed and compressive strength under dry and hygroscopic conditions were evaluated. The amount of water absorbed and compressive strength under dry condition of TEGAMA resin indicated almost same value of TEGDMA resin. The degree of the decrease of compressive strength under hygroscopic condition of TEGAMA resin was smaller than that of TEGDA resin. Therefore, it is concluded that the acrylate-methacrylate monomer is able to improve the photopolymerization ability of dimethacrylate and mechanical properities of the photocured acrylate-methacrylate resin is superior to the light-cured acrylate resin.