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 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.

Keywords

acid etching adhesion dental bonding dentin-bonding agents self-etching primer.

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References

Antonucci JM , Venz S. ( 1987). Tertiary amine salts and complexes as chemical and photochemical accelerators (abstract). J Dent Res 66:128.

Antonucci JM , Stansbury JW , Farahani M. (1992). Polymerization of dental resins via acid-amine interactions (abstract). J Dent Res 71:239.

Antonucci JM , Bennett PS , Code JE ( 1994). Effect of redox metals on dentin bonding with PMDM/Nphenyliminodiacetic acid (abstract). J Dent Res 73:277.

Blosser RL , Bowen RL (1988). Effects of purified ferric oxalate/nitric acid solutions as a pretreatment for the NTG-GMA and PMDM bonding system. Dent Mater 4:225-231.

Bowen RL (1965). Adhesive bonding of various materials to hard tooth tissue. I. Method of determining bond strength. J Dent Res 44:690-695.

Bowen RL , Cobb EN , Rapson JE (1982). Adhesive bonding of various materials to hard tooth tissues: Improvement in bond strength to dentin. J Dent Res 61:1070-1076.

Bowen RL , Tung MS , Blosser RL , Asmussen E. (1987). Dentine and enamel bonding agents. Int Dent J 37:158-161.

Bryson A. , Davies NR , Serjeant EP (1963). The ionization constants of N-(substituted-phenyl)-glycines . J Am Chem Soc 85:1933-1938.

Budavari S , editor (1989). The Merck Index. 11th ed. Rahway, NJ: Merck & Co., Inc., p. 1158.

10.

Chen R. -S, Bowen RL (1989). The use of N-phenylglycine in a dental adhesive system. J Adhesion Sci Technol 3:49-54.

11.

Cobb EN , Blosser RL , Bowen RL , Johnston AD (1989). Ferric oxalate with nitric acid as a conditioner in an adhesive bonding system. J Adhesion 28:41-49.

12.

Code JE , Antonucci JM , Bennett PS (1994). Photoactivated dentin bonding with N-phenyliminodiacetic acid (abstract). J Dent Res 73:223.

13.

Duncan DB (1955). Multiple range and multiple F tests. Biometrics 11:1-45.

14.

Farahani MF , Johnston AD , Bowen RL (1991). The effect of catalyst structure on the synthesis of a dental restorative monomer. J Dent Res 70:67-71.

15.

Harnirattisai C. , Inokoshi S. , Shimada Y. , Hosoda H. (1993). Adhesive interface between resin and etched dentin of cervical erosion/abrasion lesions. Oper Dent 18:138-143.

16.

Inokoshi S. , Hosoda H. , Harnirattisai C. , Shimada Y. (1993). Interfacial structure between dentin and seven dentin bonding systems revealed using argon ion beam etching. Oper Dent 18:8-16.

17.

Johnston AD , Asmussen E. , Bowen RL (1989). Substitutes for N-phenylglycine in adhesive bonding to dentin. J Dent Res 68:1337-1344.

18.

Miniotis NJ , Bennett PS , Johnston AD (1993). Molar efficiency study of chlorinated NPG substitutes in dentin bonding. J Dent Res 72:1045-1049.

19.

Nakabayashi N. (1992). Adhesive bonding with 4-META. Oper Dent (Suppl 5):125-130.

20.

Neter J. , Wasserman W. , Kutner MH (1990). Multifactor analysis of variance. In: Applied linear statistical models. 3rd ed. Homewood, IL: Richard D. Irwin, Inc., pp. 686-687.

21.

SAS Institute, Inc. (1987). SAS/STAT software and user's guide. Release 6.0 3ed. Cary, NC: SAS Institute, Inc .

22.

Schumacher GE , Eichmiller FC , Antonucci JM (1992). Effects of surface-active resins on dentin/composite bonds. Dent Mater 8:278-282.

23.

Tichane RM , Bennett WE (1957). Coordination compounds of metal ions with derivatives and analogs of ammoniadiacetic acid. J Am Chem Soc 79:1293-1296.

24.

Van Meerbeek B. , Inokoshi S. , Braem M. , Lambrechts P. , Vanherle G. (1992). Morphological aspects of the resin-dentin interdiffusion zone with different dentin adhesive systems. J Dent Res 71:1530-1540.

25.

Wall FJ ( 1986). Duncan's multiple comparisons test. In: Statistical data analysis handbook. New York: McGraw-Hill, Inc., pp. 4.10-4.11, 15.3.