This Article Abstract Full Text (PDF) Alert me when this article is cited Alert me if a correction is posted Citation Map Services Email this article to a friend Similar articles in this journal Similar articles in PubMed Alert me to new issues of the journal Add to Saved Citations Download to citation manager Request Permissions Request Reprints Add to My Marked Citations Citing Articles Citing Articles via Google Scholar Citing Articles via Scopus Google Scholar Articles by Schumacher, G.E. Articles by Code, J.E. Search for Related Content PubMed PubMed Citation Articles by Schumacher, G.E. Articles by Code, J.E. Social Bookmarking                         What's this?

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.

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.[Medline] [Order article via Infotrieve]
• 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.[Medline] [Order article via Infotrieve]
• 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.
• Chen R.-S, Bowen RL (1989). The use of N-phenylglycine in a dental adhesive system. J Adhesion Sci Technol 3:49-54.
• 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.
• Code JE, Antonucci JM, Bennett PS (1994). Photoactivated dentin bonding with N-phenyliminodiacetic acid (abstract). J Dent Res 73:223.
• Duncan DB (1955). Multiple range and multiple F tests. Biometrics 11:1-45.[Medline] [Order article via Infotrieve]
• 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.
• 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.[Medline] [Order article via Infotrieve]
• 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.[Medline] [Order article via Infotrieve]
• Johnston AD, Asmussen E., Bowen RL (1989). Substitutes for N-phenylglycine in adhesive bonding to dentin. J Dent Res 68:1337-1344.
• Miniotis NJ, Bennett PS, Johnston AD (1993). Molar efficiency study of chlorinated NPG substitutes in dentin bonding. J Dent Res 72:1045-1049.
• Nakabayashi N. (1992). Adhesive bonding with 4-META. Oper Dent (Suppl 5):125-130.
• 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.
• SAS Institute, Inc. (1987). SAS/STAT software and user's guide. Release 6.03ed. Cary, NC: SAS Institute, Inc.
• Schumacher GE, Eichmiller FC, Antonucci JM (1992). Effects of surface-active resins on dentin/composite bonds. Dent Mater 8:278-282.[Medline] [Order article via Infotrieve]
• Tichane RM, Bennett WE (1957). Coordination compounds of metal ions with derivatives and analogs of ammoniadiacetic acid. J Am Chem Soc 79:1293-1296.
• 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.
• 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.

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


CiteULike    Complore    Connotea    Del.icio.us    Digg    Reddit    Technorati    Twitter    What's this?

This Article Abstract Full Text (PDF) Alert me when this article is cited Alert me if a correction is posted Citation Map Services Email this article to a friend Similar articles in this journal Similar articles in PubMed Alert me to new issues of the journal Add to Saved Citations Download to citation manager Request Permissions Request Reprints Add to My Marked Citations Citing Articles Citing Articles via Google Scholar Citing Articles via Scopus Google Scholar Articles by Schumacher, G.E. Articles by Code, J.E. Search for Related Content PubMed PubMed Citation Articles by Schumacher, G.E. Articles by Code, J.E. Social Bookmarking                         What's this?