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

具有优异可见光聚合能力的新型单体的合成及其在牙科领域的应用

基本信息

批准号：
01550711
负责人：
NAKABAYASHI Nobuo
金额：
$ 1.15万
依托单位：
Tokyo Medical and Dental University
依托单位国家：
日本
项目类别：
Grant-in-Aid for General Scientific Research (C)
财政年份：
1989
资助国家：
日本
起止时间：
1989 至 1990
项目状态：
已结题

项目摘要

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.

为了提高光固化丙烯酸酯树脂在吸湿条件下的力学强度，合成了一种分子中同时含有丙烯酰基和甲基丙烯酰基的新型单体--丙烯酸-甲基丙烯酸三乙二醇酯（TEGAMA）。比较了TEGAMA与三甘醇的二甲基丙烯酸酯（TEGDMA）和二丙烯酸酯（TEGDA）的光聚合能力和力学性能（抗压强度）。用可见光（λ>400 nm）照射含有0.5重量%的樟脑醌和N，N-二甲基氨基苯甲酸乙酯作为光引发剂的可光固化单体。当进行30秒的光照射时，侧链中的残留单体和未反应双键的量均高于TEGDMA树脂。但是，从60秒照射开始，TEGAMA树脂的这些值小于TEGDMA树脂的这些值。在整个光照过程中，TEGAMA树脂侧链中丙烯酰基的残留量高于甲基丙烯酰基的残留量。从上述结果可以推测TEGAMA的光聚合机理是甲基丙烯酰基在一定程度上相互反应，然后由于侧链上残留的丙烯酸酯基团比甲基丙烯酰基具有更高的反应活性而进行进一步的高交联反应。评价了干燥和吸湿条件下的吸水量和抗压强度。TEGAMA树脂的吸水量和干压强度与TEGDMA树脂相差不大。在吸湿条件下，TEGAMA树脂的抗压强度下降幅度小于TEGDA树脂。因此，丙烯酸酯-甲基丙烯酸酯单体能够提高二甲基丙烯酸酯的光聚合能力，光固化丙烯酸酯-甲基丙烯酸酯树脂的力学性能优于光固化丙烯酸酯树脂的上级性能。