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Hydrolysis of Functional Monomers in a Single-bottle Self-etching Primer—Correlation of ¹³C NMR and TEM Findings

¹ Department of Dental Materials and
⁴ Department of Operative Dentistry, Nihon University School of Dentistry at Matsudo, Chiba, Japan;
² Department of Oral Biology and Maxillofacial Pathology, School of Dentistry, Medical College of Georgia, Augusta, GA, USA;
³ Paediatric Dentistry and Orthodontics, Faculty of Dentistry, The University of Hong Kong, Prince Philip Dental Hospital, 34 Hospital Road, Hong Kong SAR, China; and
⁵ Department of Research and Development, Shofu Inc., Kyoto, Japan

Correspondence: ^* corresponding author, Franklintay{at}gmail.com

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.

Key Words: hydrolysis • single-bottle • 4-MET • self-etching • nuclear magnetic resonance

Journal of Dental Research, Vol. 85, No. 5, 422-426 (2006)
DOI: 10.1177/154405910608500505


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