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N-phenyliminodiacetic Acid as an Etchant/Primer for Dentin Bonding

Clinical Center/CODC, National Institutes of Health, Bethesda, Maryland 20892

J.M. Antonucci

Dental and Medical Materials Group, Polymers Division, National Institute of Standards and Technology, Gaithersburg, Maryland 20899

P.S. Bennett

American Dental Association Health Foundation, Paffenbarger Research Center, National Institute of Standards and Technology, Gaithersburg, Maryland 20899

J.E. Code

Clinical Center/CODC, National Institutes of Health, Bethesda, Maryland 20892

Effective composite-to-dentin bonding has been achieved by the sequential use of dilute aqueous nitric acid (HNO₃) and acetone solutions of N-phenylglycine and a carboxylic acid monomer, e.g., p-PMDM. Both the HN03 pre-treatment and the surface-initiated polymerization that results from reaction of infused N-phenylglycine and PMDM have been identified as key elements of this bonding system. In this study, N-phenyliminodiacetic acid, a unique imino acid derivative with acidic and chelating potential, was evaluated as a dual etchant/primer for dentin bonding. A randomized, 23 factorial design was used to study the effects of 3 factors on tensile bond strength (TBS): conditioner (HN03 vs. no HNO₃), primer (N-phenylglycine vs. N-phenyliminodiacetic acid), and primer solvent (acetone vs. acetone:H20). The three-step protocol consisting of HNO₃, N- phenylglycine in acetone, and PMDM in acetone served as the control. The hypothesis tested was that N-phenyliminodiacetic acid could act as both an effective conditioner (i.e., etchant) and as a primer. Two-step protocols that included only N-phenyliminodiacetic acid and PMDM were compared with the control. TBS (n = 10 per group) were determined after 24-hour storage in H₂O and analyzed by ANOVA and Duncan's Multiple Range test. Primer solvent was critical for obtaining significant bonding to dentin when HNO₃ was omitted. N-phenyliminodiacetic acid in acetone without prior HNO₃ etching gave the lowest ranking mean TBS (95% CI, 3.8 ± 1.9 MPa). In contrast, the mean TBS obtained from samples treated with N-phenyliminodiacetic acid in acetone:H₂O without prior HN03 etching was not statistically different (p > 0.05) from the mean TBS for the control (95% CI, 9.3 ± 1.8 and 9.8 ± 1.9 MPa, respectively). Due to its dual function as etchant and primer, N-phenyliminodiacetic acid in acetone:H₂O provides for a simplified bonding technique that yields strong, PMDM-mediated adhesion to dentin.

Key Words: acid etching • adhesion • dental bonding • dentin-bonding agents • self-etching primer.

Journal of Dental Research, Vol. 76, No. 1, 602-609 (1997)
DOI: 10.1177/00220345970760011201


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