The pKa effects of the carboxylic acid in N-methacryloyl-omega-amino acid on the demineralization and bond strengths to the teeth.

It is understood that the application of a self-etching primer to the tooth enhances the bonding of the resin to the tooth. In this study, we designed a self-etching primer consisting of a series of three N-methacryloyl-omega-amino acids (NMomegaA) with different methylene chain lengths. The demineralization aspect of the teeth components by the carboxylic acid in the NMomegaA and its effects on the bond strength of the resin to the tooth were examined. The amount of decalcification of the hydroxyapatite or dentin by the carboxylic acid in the NMomegaA was strongly dependent on the carboxylic acid's pKa value in the NMomegaA. However, the bond strength's mean values for both the enamel and dentin were not influenced by the degree of demineralization by the carboxylic acid in the NMomegaA. The greater mean value of the dentin's bond strength than with the enamel's was due to differences in the adhesion mechanism types, since the NMomegaA not only exhibited an etching efficacy but also a priming efficacy to the collagen that had been exposed by the NMomegaA conditioning. Copyright 2003 Elsevier Ltd.