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

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.

Ethyl‐4‐(Dimethylamino) benzoate initiation of the spontaneous polymerization of aqueous acidic adhesive formulations in the presence of a base

“…With regard to the second question of why such a dependency of the polymerization behavior on pH was not noticed before for systems similar to ours, we could find the answer in the proposed mechanism (Scheme ) as well. Our aromatic amine (4E) was distinctively different from the aromatic amines that were reported to trigger the spontaneous polymerization without additional activators. That is, those amines [including NPG, N ‐ p ‐tolyl glycine, and N ‐phenyl iminodiacetic acid (PIDDA)] all bore carboxylic acid functional groups themselves, whereas 4E did not.…”

Light-Cured Self-Etch Adhesives Undergo Hydroxyapatite-Triggered Self-Cure

“…Despite the long span of publication (Uehara 1958(Uehara , 1960Kotal et al 2010;Sato et al 1981), this initiation did not garner much attention in the dental field. To our knowledge, only in the 1990s were there investigations of carboxyl-bearing secondary/ tertiary amines (e.g., N-phenylglycine, N-phenyliminodiacetic acid) in dentin bonding (Antonucci et al 1992;Farahani et al 1997;Schumacher et al 1997). However, these amines share the same drawback of regular chemical initiators in spontaneity possibly due to the coexistence of acid and amine on the same molecule so that the acid-amine balance is always maintained (Bai et al 2013).…”

Indentation Damage and Mechanical Properties of Human Enamel and Dentin

“…After being polished, the teeth were stored in distilled water. To reveal the enamel structure, two teeth of occlusal section were etched with 10% H3P04 gel (Bisco, Itasca, IL) for 10 sec, and two teeth of axial section were etched with 2.5% HNO3 and 6.3% N-phenyliminodiacetic acid for 30 sec (Schumacher and Antonucci, 1997).…”