Synthesis Of Light-Cured Acrylate Functional Monomers And Their Polymer Properties

In recent years, bonding of composite resin to dental alloys is being widely employed in restorative dentistry. Adhesive agents that could promote chemical integration between composite resin and dental alloys and significantly elevate the bond strengths of the composite resin joined to dental alloy. Acrylate and their derivatives are usually used as adhesive agents in dentistry because not only they have fine biological compatibility, good physicomechanical property, but also they have well bonding property on composite resin.In this thesis, the experiments include three parts: firstly, active monomers and adhesive monomers are synthesized;secondly, polymer are prepared under UV irradiation and testing bond strengths;thirdly, self-assembled monolayer-protected gold nanoparticles are obtained.Firstly, three active monomers are synthesized. Pentaerythritol triacrylate and pentaerythritol tetraacrylate are synthesized from the reaction of pentaerythritol with acrylic acid by direct esterification. Triethylene glycol diacrylate is synthesized from triethylene glycol, acrylic acid and thionyl chloride using the method of acyl chloride. Secondly, six adhesive monomers are prepared. 10-methacryloyloxydecyl dihydrogen phosphate and 10-methacryloyloxydecyl thiophosphoric acid dichloride are respectively prepared by the reaction of 10-hydroxy-decyl-methacrylate with phosphoryl chloride or thiophosphoryl chloride. 5-carboxy-2-thiouracil is synthesized from thiouracil and diethyl ethoxymethylene malonate via combination, hydrolysis reaction. 10-methacryloyloxydecyl-2-thiouracil-5-carboxylate is prepared by 5-carboxy-2-thiouracil and 10-hydroxy-decyl-methacrylate as raw materials using DCC as dehydrating agent. Using the same method the other three adhesive monomers are synthesized. The structure of products are characterized by ¹H-NMR, ³¹P-NMR, FT-IR and MS. Finally, adhesive and active monomers could polymerize under the UV exposure by using camphorquinone as photoinitiator and the effect of different adhesive agents on the bond durability of composite resin joined to dental alloy are investigated in this paper. Representative debonded specimens are characterized by scanning electron micrographs. A water-soluble gold nanoparticle is prepared with trisodium citrate and hydrogen tetrachloroaurate by reduction method. Using thiotic acid-6-methacryloyloxyhexyl ester as a self-assembled molecule, self-assembled monolayer-protected gold nanoparticles are obtained.The experimental results indicate that 10-methacryloyloxydecyl dihydrogen phosphate and 10-methacryloyloxydecyl thiophosphoric acid dichloride could significantly elevate thebond strengths of the composite resin joined to Ti and Co-Cr alloy;the most durable bond are obtained between composite resin and Au alloy by using 10-methacryloyloxydecyl-2-thiouracil-5-carboxylate or thiotic acid-6-methacryloyloxyhexyl ester as adhesive agents. The Au-S chemical bond is formed between thiotic acid-6-methacryloyloxyhexyl ester and gold nanoparticle.