Trace of organic sulfur compounds detected from debonded interface between transparent acrylic resin and gold alloy

The purpose of the current study was to evaluate the bonding performance of two single-liquid primers, which contained 6-(4-vinylbenzyl-n-propyl) amino-1,3,5-triazine-2,4-dithione (VTD) or 6-methac-ryloyloxyhexyl 2-thiouracil 5-carboxylate (MTU-6), used for bonding between metals and an acrylic resin. A gold alloy and high-purity titanium were used as adherend materials, and a transparent acrylic resin initiated with tri-n-butylborane derivative was selected as the luting material. Both adherends were treated with one of the primers and bonded with the luting material, after which shear bond strength was determined. Fourier transform infrared spectroscopy was used to analyze debonded resin specimens. Shear bond strength to gold alloy was significantly greater than that to titanium for both the VTD and MTU-6 primers. A trace of thiol structure, probably derived from VTD and MTU-6, was detected on resin surfaces debonded from gold alloy. These results indicate that the two organic sulfur compounds, which are stable in an atmospheric environment, are tautomerized into a thiol structure, thus allowing adsorption onto noble metals. In addition, the adsorbed thiol compounds contribute to chemical bonding between the acrylic resin and noble metal alloy, as polymerizable adhesive functional monomers.