Divanillates and polymerizable vanillates as ingredients of dental cements

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.