Hydrolysis of functional monomers in a single-bottle self-etching primer - Correlation of 13C NMR and TEM findings

N. Nishiyama, F. R. Tay, K. Fujita, D. H. Pashley, K. Ikemura, N. Hiraishi, N. M. King

Research output: Contribution to journalArticlepeer-review

53 Scopus citations


Self-etching primers/adhesives that combine acidic methacrylate monomers with water in a single bottle are hydrolytically unstable and require refrigeration to extend their shelf-lives. This study tested the null hypothesis that one year of intermittent refrigeration of a 4-MET-containing simplified self-etching primer does not result in hydrolytic changes that are identifiable by transmission electron microscopy and 13C NMR spectroscopy. Human dentin was bonded with UniFil Bond immediately after being unpacked, or after one year of intermittent refrigeration at 4°C. Fresh and aged primers were analyzed by NMR for chemical changes. Ultrastructural observations indicated that there was an augmentation in etching capacity of the aged adhesive that was not accompanied by resin infiltration or effective polymerization. New NMR peaks detected from the aged ethanol-based primer confirmed that degradation occurred initially via esterification with ethanol, followed by hydrolysis of both ester groups in the 4-MET. Hydrolysis of functional methacrylate monomers occurs despite intermittent refrigeration.

Original languageEnglish (US)
Pages (from-to)422-426
Number of pages5
JournalJournal of Dental Research
Issue number5
StatePublished - May 2006


  • 4-MET
  • Hydrolysis
  • Nuclear magnetic resonance
  • Self-etching
  • Single-bottle

ASJC Scopus subject areas

  • Dentistry(all)


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