Synthesis and evaluation of new phosphonic,bisphosphonic and difluoromethylphosphonic acid monomers for dental application |
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Authors: | Yohann Catel Vincent Besse Anaïs Zulauf David Marchat Emmanuel Pfund Thi-Nhàn Pham Didier Bernache-Assolant Michel Degrange Thierry Lequeux Pierre-Jean Madec Loïc Le Pluart |
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Institution: | 1. Laboratoire de Chimie Moléculaire et Thioorganique, UMR CNRS 6507, INC3M, FR 3038, ENSICAEN & Université de Caen, 14050 Caen, France;2. Unité de Recherche Biomatériaux et Interfaces, Faculté de Chirurgie Dentaire, Université Paris Descartes, 1 rue Maurice Arnoux, 92120 Montrouge, France;3. Centre Ingénierie et Santé, Ecole Nationale Supérieure des Mines de Saint-Etienne, 158 cours Fauriel, 42023 Saint-Etienne Cedex 2, France |
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Abstract: | Syntheses of novel 5-(methacryloyloxy)pentylphosphonic acid 1, 5-(methacryloyloxy)pentylidenebisphosphonic acid 2 and 1,1-difluoro-5-(methacryloyloxy)pentylphosphonic acid 3 are described. The ability of these monomers to adhere to hydroxyapatite was demonstrated using 31P CP-MAS NMR spectroscopy. Their copolymerization with N,N′-diethyl-1,3-bis(acrylamido)propane (DEBAAP) was investigated with photo differential scanning calorimetry. These mixtures exhibit a significantly higher reactivity than DEBAAP alone. Bisphosphonic acid 2 was shown to be significantly more reactive than monomers 1 and 3. Adhesive properties of these monomers were also studied. Adhesives based on bisphosphonic acid 2 and difluoromethylphosphonic acid 3 provide significantly higher dentin shear bond strength than the one based on phosphonic acid 1. |
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