Synthesis,photopolymerization, and adhesive properties of new bisphosphonic acid monomers for dental application |
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| Authors: | Yohann Catel Michel Degrange Loïc Le Pluart Pierre‐Jean Madec Thi‐Nhàn Pham Fei Chen Wayne D Cook |
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| Institution: | 1. Laboratoire de Chimie Moléculaire et Thio‐organique, ENSICAEN, Université de Caen Basse‐Normandie, CNRS;2. 6 boulevard du Maréchal Juin, 14050 Caen, France;3. Unité de Recherche Biomatériaux et Interfaces, Faculté de Chirurgie Dentaire, Université Paris Descartes, 1 rue Maurice Arnoux, 92120 Montrouge, France;4. Department of Materials Engineering, Monash University, Clayton, Victoria 3800, Australia |
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| Abstract: | Four new monomers, 3‐(N‐methylacrylamido)propylidenebisphosphonic acid, 3‐(N‐propyl‐acrylamido)propylidenebisphosphonic acid, 3‐(N‐hexylacrylamido)propylidenebisphosphonic acid, and 3‐(N‐octylacrylamido)propylidenebisphosphonic acid, have been synthesized in good yields and fully characterized by 1H, 13C, 31P NMR, and HRMS. The copolymerization of these monomers with N,N′‐diethyl‐1,3‐bis(acrylamido)propane (DEBAAP) has been investigated with differential scanning calorimetry. These mixtures show a higher reactivity than DEBAAP. New self‐etch dental primers, based on these acrylamide monomers, have been formulated. Dentin shear bond strength measurements have shown that primers based on these bisphosphonic acids assure a strong bond between the tooth substance and a dental composite. © 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 47: 5258–5271, 2009 |
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| Keywords: | acrylamide adhesives bisphosphonic acid dental polymers photopolymerization synthesis |
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