N-phenyliminodiacetic acid as an etchant/primer for dentin bonding

J Dent Res. 1997 Jan;76(1):602-9. doi: 10.1177/00220345970760011201.

Abstract

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 HNO3 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, 2(3) factorial design was used to study the effects of 3 factors on tensile bond strength (TBS): conditioner (HNO3 vs. no HNO3), primer (N-phenylglycine vs. N-phenyliminodiacetic acid), and primer solvent (acetone vs. acetone:H2O). 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 HNO3 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.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Acid Etching, Dental / methods*
  • Analysis of Variance
  • Dentin / ultrastructure
  • Dentin-Bonding Agents / chemistry*
  • Glycine / analogs & derivatives
  • Glycine / chemistry
  • Humans
  • Imino Acids / chemistry*
  • Materials Testing
  • Microscopy, Electron, Scanning
  • Statistics, Nonparametric
  • Surface Properties
  • Tensile Strength

Substances

  • Dentin-Bonding Agents
  • Imino Acids
  • N-phenyliminodiacetic acid
  • N-phenylglycine
  • Glycine
  • iminodiacetic acid