Isocyanato urethane methacrylates were synthesized from five diisocyanates and hydroxyethyl methacrylate. They may be homopolymerized or copolymerized with other methacrylates by the usual free radical methods of initiation and have potential as adhesion-promoting agents for dentin.
Get full access to this article
View all access options for this article.
References
1.
Buonocore, M.G. : A Simple Method of Increasing the Adhesion of Acrylic Filling Materials to Enamel Surfaces, J Dent Res34:849-853,1955.
2.
Buonocore, M.G. : "Bonding to Hard Dental Tissues," Adhesion in Biological Systems, Manly, R. S. (ed.), New York: Academic Press, 1970, pp. 225-254.
3.
Kopel, H.M.: Pretreating Enamel to Increase Adhesion of Plastic Restorative Materials - The Etch Technic, J S Calif Dent Assoc39:752-755, 1971.
4.
Lee, B.D. ; Phillips, R.W.; and Swartz, M.L.: The Influence of Phosphoric Acid Etching on the Retention of Acrylic Resin to Bovine Enamel, JADA82:1381-1386, 1971.
5.
Sharp, E.C. and Grenoble, D.E.: Dental Resin Penetration into Acid Etched Subsurfaces of Enamel, J S Calif Dent Assoc39:741-746,1971.
6.
Brauer, G.M. and Termini, D.J.: Bonding of Bovine Enamel to Restorative Resin: Effects of Pretreatment of Enamel, J Dent Res50:151-160,1972.
7.
Bowen, R.L.: Surface Active Comonomer and Method of Preparation. U S Patent 3,200,142 (Aug. 10, 1965).
8.
Bowen, R.L.: Adhesive Bonding of Various Materials to Hard Tooth Tissues. II. Bonding to Dentin Promoted by a Surface-Active Comonomer, J Dent Res44:895-902, 1965.
9.
Bowen, R.L.: Adhesive Bonding of Various Materials to Hard Tooth Tissues. III. Bonding to Dentin Improved by Pretreatment and the Use of a Surface-Active Comonomer , J Dent Res44:903-905, 1965.
10.
Bowen, R.L.: Adhesive Bonding of Various Materials to Hard Tooth Tissues. IV. Bonding to Dentin, Enamel, and Fluorapatite Improved by the Use of a Surface-Active Comonomer, J Dent Res44:906-911, 1965.
11.
Bowen, R.L.: Adhesive Bonding of Various Materials to Hard Tooth Tissues. V. The Effect of a Surface-Active Comonomer on Adhesion to Diverse Substrates, J Dent Res44:1369-1373,1965.
12.
Chandler, H.H. ; Bowen, R.L.; Paf-Fenbarger , G.C.; and Mullineaux, A.L.: Clinical Evaluation of a Radiopaque Composite Restorative Material After Three and One-Half Years, J Dent Res52 :1128-1137, 1973.
13.
Retief, D.H.: Laboratory Evaluation of the Tensile Adhesive Bond Strength of a Composite Dental Restorative System Containing a Surface-Active Comonomer to Enamel and Dentine, J Dent Assn S Afr30: 595-601, 1975.
14.
Misra, D.N. and Bowen, R.L.: Adhesive Bonding of Various Materials to Hard Tooth Tissues. XI. Chemisorption of the Adduct of Diglycidyl Ether of Bisphenol A with N-Phenylglycine on Hydroxyapatite, J Phys Chem80:842-846, 1977.
15.
Misra, D.N. and Bowen, R.L.: Adhesive Bonding of Various Materials to Hard Tooth Tissues. XII. Adsorption of N-(2-Hydroxy-3-methacryloxypropyl)N-Phenylglycine (NPG-GMA) on Hydroxyapatite, J Colloid Interface Sci61:14-20, 1977.
16.
Buonocore, M.G.: "The Challenge of Bonding to Dentin, The Acid Etch Technique," Proceedings of an International Symposium held at the Suvretta House Hotel, St. Moritz, Switzerland Dec. 16-18, 1974, North Central Pub. Co., St. Paul, Minn., pp. 139-156.
17.
Lee, H.L. : Adhesion Between Living Tissues and Plastics. I. Adhesion of Epoxy and Polyurethane Resins to Dentin and Enamel, J Biomed Mater Res3:349-367, 1969.
18.
Lee, H.L., JR and Swartz, M.L.: "Surface Preparation and Various Adhesive Resins," Adhesion in Biological Systems, Manly, R. S. (ed), New York: Academic Press, 1970, pp. 269-289.
19.
Fookson, A. : IADR Prog & Abst49: No. 403, 1970.
20.
Brauer, G.M. and Huget, E.F.: "Dental Adhesives," The Chemistry of Biosurfaces, Vol. 2, Hair, M. L. (ed.), New York: Marcel Dekker, Inc., 1972 , pp. 731-800.
21.
Brauer, G.M.: "Adhesion and Adhesives," Scientific Aspects of Dental Materials, von Fraunhofer, J. A. (ed.), London and Boston: Butterworths, 1975, pp. 49-96.
22.
Bowen, R.L. : Adhesive Bonding of Various Materials to Hard Tooth Tissue. IX. The Concept of Polyfunctional Surface-Active Comonomers , Presented at the 7th National Bureau of Standards In-Action Seminar, "Health Related Activities,"Gaithersburg , Maryland, December 14, 1973. J Biomed Mater Res 9:501-510, 1975.
23.
Bowen, R.L.: Adhesive Bonding of Various Materials to Hard Tooth Tissue. VII. Metal Salts as Mordants for Coupling Agents, in Dental Adhesive Materials , Moskowitz, H. D.: Ward, G. T.; and Woolridge, E. D. (eds.), Proceedings from the Symposium held Nov. 8-9, 1973, at the Hunter-Bellevue School of Nursing, New York City , Prestige Graphic Services, 1974 , pp. 205-221.
Sanders, J.H. ; and Slocombe, R.J.: The Chemistry of Organic Isocyanates, Chem Rev43:203-218, 1948.
26.
Arnold, R.G. ; Nelson, J.A.; and Ver-Banc , J.J.: Recent Advances in Isocyanate Chemistry, Chem Rev57:47-76, 1957.
27.
Eastoe, J.E.: "Intact Collagen," Treatise on Collagen, Vol. I, Composition of Collagen and Allied Proteins, Ramachandran, G. N. (ed.), London and New York: Academic Press, 1967, Chap. I, pp. 1-72.
28.
Zemskova, Z.G. ; Matveyeva, N.G.; and Berlin, A.A.: The Synthesis and Some Properties of Oligo(oxyethylene-urethane methacrylates), Polymer Sci USSR15:814-822, 1973.
29.
David, D.J. and Stanley, H.B.: Analytical Chemistry of the Polyurethanes, Vol. XVI, Part III, New York, London, Sydney and Toronto: Wiley-Interscience, 1969, Chap. III, pp. 86-90.
30.
Frisch, K.C. ; Klempner, D.; and Mig-Dal , S.: Polyurethane-Polyacrylate Interpenetrating Networks II, J Appl Polym Sci19:1893-1904 (1975).
