Oligomers with Pendant Isocyanate Groups as Adhesives for Dentin and Other Tissues

Abstract

Oligomers containing pendant isocyanate groups were synthesized from various vinyl monomers, m-isopropenyldimethylbenzyl isocyanate (TMI), and 2-isocyanatoethyl methacrylate (IEM). The liquids were characterized by their refractive indices, infrared spectra, and percentage of isocyanate groups in the molecule. Adhesive properties of these compounds were compared with those of oligomers prepared from methacrylate esters, IEM, and/or TMI which had been synthesized previously. Bond strengths of the sodium salt of ethylenediaminetetraacetic acid (Na₂EDTA adjusted to pH 7.4) and glutaraldehyde-treated dentin cemented to composite resin with dilute solutions of the oligomers and then stored in water were determined by the procedure of Kemper and Kilian (1975). These adhesive compositions, especially formulations synthesized from vinyl monomers, adhered at least as well to dentin as did other dentin bonding agents. Oligomers synthesized with methacrylate esters bonded more strongly to bone than did other hard-tissue adhesives. These oligomeric compositions are also excellent soft-tissue adhesives. For example, they provide a strong bond between a collagenous substrate (such as calfskin) and cured denture-base resin. Provided that their biological properties prove satisfactory, these compositions could find many applications as hard-and soft-tissue adhesives in clinical dentistry.

Get full access to this article

View all access options for this article.

References

Asmussen, E. and Munksgaard, E.C. (1986): Adhesion Promoting Agent and its Use on Collagenous Material, U.S. Patent 4,593, 054, Assigned to Bayer, A.G., Leverkusen, West Germany.

Bowen, R.L. (1965): Adhesive Bonding of Various Materials to Hard Tissues I. Method of Determining Bond Strength, J Dent Res 44:690-695.

Bowen, R.L. (1985): Method for Obtaining Strong Adhesive Bonding of Composites to Dentin, Enamel and Other Substrates, U.S. Patent 4,514, 527, April 30; U.S. Patent 4, 521, 550, June 4.

Bowen, R.L. (1987): Simplified Method for Obtaining Strong Adhesive Bonding of Composites to Dentin, Enamel and other Substrates, U.S. Patent 4, 659, 751, April 21.

Bowen, R.L. and Cobb, E.N. (1983): A Method of Bonding to Dentin and Enamel, J Am Dent Assoc 107:734-736.

Brauer, G.M. ; Kumpula, J. ; Termini, D.J. ; and David-Son, K.M. (1979): Durability of the Bond Between Bone and Various 2-Cyanoacrylates in an Aqueous Environment, J Biomed Mater Res 13:593-606.

Brauer, G.M. and Lee, C.H. (1989a): Oligomers with Pendant Isocyanate Groups as Tissue Adhesives, I. Synthesis and Characterization, J Biomed Mater Res (in press).

Brauer, G.M. and Lee, C.H. (1989b): Oligomers with Pendant Isocyanate Groups as Tissue Adhesives, II. Adhesion to Bone and Other Tissues, J Biomed Mater Res (in press).

Cranley, P.E. (1984): Isocyanatoethyl Methacrylate: A Latent Crosslinker for Coating or Adhesive Resins. In: Adhesive Chemistry, C.H. Lee , Ed., New York, NY: Plenum Publishing Co., pp. 765-784.

10.

Dexter, R.W. ; Saxon, R. ; and Fiori, D.E. (1985): mTMI- a Novel Unsaturated Isocyanate, Polym Mat Science and Eng 53 :534-539.

11.

Kemper, R. and Kilian, R. (1975): New Test System for Tensile Bond Strength Testing , IADR Prog & Abst 55: No. 308.

12.

Lacefield, W.R. ; Reindl, M.C. ; and Retief, D.H. (1985): Tensile Bond Strength of a Glass Ionomer Cement , J Prosthet Dent 53:194-198.

13.

Munksgaard, E.C. and Asmussen, E. (1984): Bone Strength Between Dentin and Restorative Resins Mediated by Mixtures of HEMA and Glutaraldehyde, J Dent Res 63:1087-1089.

14.

Munksgaard, E.C. ; Irie, M. ; and Asmussen, E. (1985): Dentin-polymer Bond Promoted by Gluma and Various Resins, J Dent Res 64:1409-1411.

15.

Snell, F.D. and Ettre, L.S. , Eds. (1974): Encyclopedia of Industrial Chemical Analysis, Vol. 19, New York: Interscience, p. 272.

16.

Thomas, M.R. (1982): Isocyanatoethyl Methacrylate: A Heterofunctional Monomer for Polyurethane and Vinyl Polymer Systems, Org Coatings and Polymer Sci Proc 46:506-513.

17.

Tukey, J.W. (1949): Comparing Individual Means in the Analysis of Variance, Biometrics 5:99-114.