Studies on Adhesion to Tooth Substrate

II. Synthesis and Adhesiveness of Monomers that have Amide Groups

Abstract

The synthesis and adhesiveness of monomers that have amide groups as hydrophilic groups, i.e. 4-methacryloxybenzamide (MBA) and 4-methacyloylphenylpropionamide (MPPA) are reported.
MBA was prepared from the reaction of p-hydroxybenzamide with methacryloyl chloride in an alkaline solution. MPPA was prepared from the reaction of p-hydroxyphenylpropionamide with methacryloyl chloride in trifluoroacetic acid.
The bovine enamel and dentin were etched by a 10% citric acid -3% FeCl₃ (10-3) solution. The monomers were dissolved in MMA, and the adhesiveness of MMA and O-methacryloyl tyrosine amide (MTYA) were also tested. The tensile bond strengths (MPa) after 1 day at 37°C water were measured. They were MMA: 11.1±5.3 (enamel), 5.7±2.8 (dentin); MBA/MMA: 12.1±6.0 (enamel), 12.3±4.0 (dentin); MPPA/MMA: 11.8±2.5 (enamel), 12.1±3.5 (dentin); and MTYA/MMA: 11.8±3.5 (enamel), 14.1±6.1 (dentin).