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Abstract

In order to shed light on the relationship of monomer structure and adhesiveness to tooth enamel, methacrylamides having various substituents were synthesized and evaluated as dental adhesives. Among 17 methacrylamides synthesized here, those having N-m- and N-p-carbethoxyphenyl, N-p-fluorophenyl, and N-3-carboxycyclohexyl groups showed adhesive tensile strength of more than 100 kg/cm2 with minimal drops in strength on standing, indicating high potentials as novel adhesives. It was also confirmed that a carboxyl group enhances adhesive tensile strength peculiarly regardless of skeletal structures.