Effect of Carboxyl Group in O-Methacryloyl-N-Acyl Tyrosines on Adhesiveness to Unetched Human Dentin

Jiro Tanaka, Kunio Ishikawa, Hirofumi Yatani, Atsushi Yamashita, Kazuomi Suzuki

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We have reported that the carboxylic group plays an important role in the adhesion of methacryloyl amino acid - 2-hydroxyethyl methacrylate type restorative resin to dentin surfaces. However, our study so far has been limited to the methacryloyl amino acid that has only one carboxylic acid. In this investigation, three new O-methacryloyl-N-acyl tyrosines (MAATY) that have one or two carboxylic groups in the acyl group, and thus two or three carboxylic groups in MAATY, were prepared and evaluated for their bond strength to unetched dentine. Higher bond strength was observed when the MAATY contained larger number of carboxylic acid groups. Factor analysis of the bonding strength revealed that the hydrogen bond ability of the carboxylic acid and the hydrophile-lipophile balance (HLB) affected the bond strength.

Original languageEnglish
Pages (from-to)87-95
Number of pages9
JournalDental materials journal
Issue number1
Publication statusPublished - Jan 1 1999



  • Amino acid
  • HLB value
  • Hydrogen bond

ASJC Scopus subject areas

  • Ceramics and Composites
  • Dentistry(all)

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