Stansbury J W, Brauer G M
J Biomed Mater Res. 1985 Jul-Aug;19(6):715-25. doi: 10.1002/jbm.820190610.
Vanillate esters with multifunctional groups the react with metal oxides to give chain-extended molecules have been synthesized. Divanillates were obtained from vanillic acid and the corresponding polymethylenediols. Methacryloylethyl vanillate (MEV) and vanillyl methacrylates were prepared respectively from hydroxyethyl vanillate or vanillyl alcohol and methacryloyl chloride. The properties of cements prepared with liquids incorporating these compounds were determined. Liquids containing divanillates dissolved in the reactive chelating agent o-ethoxybenzoic acid (EBA) when mixed with zinc oxide powders harden within a few minutes. The resulting cements have a tensile strength much higher than the commonly used zinc oxide-eugenol cements, have low solubility, do not inhibit polymerization, and adhere well to metallic substrates. Similarly, liquids with MEV as an ingredient yield cements with excellent strength and good adhesion to stainless steel and composites. Their brittleness can be overcome by addition of an oligomeric methacryloylethyl vanillate to the liquid or silanized glass to the powder ingredient. These cements, subject to their biocompatibility to oral tissues, could be most useful for a number of dental applications.
已合成了带有多官能团的香草酸酯，它们能与金属氧化物反应生成链增长分子。双香草酸酯由香草酸和相应的聚亚甲基二醇制得。甲基丙烯酰基乙基香草酸酯（MEV）和甲基丙烯酸香草酯分别由香草酸羟乙酯或香草醇与甲基丙烯酰氯制备。测定了用含有这些化合物的液体配制的粘固剂的性能。含有双香草酸酯的液体溶解在反应性螯合剂邻乙氧基苯甲酸（EBA）中，当与氧化锌粉末混合时，几分钟内就会硬化。所得的粘固剂的拉伸强度远高于常用的氧化锌丁香酚粘固剂，溶解度低，不抑制聚合反应，并且与金属基材有良好的粘附性。同样，以MEV为成分的液体能制得强度优异且对不锈钢和复合材料有良好粘附性的粘固剂。通过向液体中添加甲基丙烯酰基乙基香草酸酯低聚物或向粉末成分中添加硅烷化玻璃，可以克服它们的脆性。考虑到这些粘固剂对口腔组织的生物相容性，它们在许多牙科应用中可能非常有用。
