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Synthesis, photopolymerization and adhesive properties of new hydrolytically stable phosphonic acids for dental applications

Authors

  • Yohann Catel,

    1. Laboratoire de Chimie Moléculaire et Thio-organique, ENSICAEN, Université de Caen Basse-Normandie, CNRS; 6 boulevard du Maréchal Juin, 14050 Caen, France
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  • Michel Degrange,

    1. Unité de Recherche Biomatériaux et Interfaces, Faculté de Chirurgie Dentaire. Université Paris Descartes, 1 rue Maurice Arnoux, 92120 Montrouge, France
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  • Loïc Le Pluart,

    Corresponding author
    1. Laboratoire de Chimie Moléculaire et Thio-organique, ENSICAEN, Université de Caen Basse-Normandie, CNRS; 6 boulevard du Maréchal Juin, 14050 Caen, France
    • Laboratoire de Chimie Moléculaire et Thio-organique, ENSICAEN, Université de Caen Basse-Normandie, CNRS; 6 boulevard du Maréchal Juin, 14050 Caen, France
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  • Pierre-Jean Madec,

    1. Laboratoire de Chimie Moléculaire et Thio-organique, ENSICAEN, Université de Caen Basse-Normandie, CNRS; 6 boulevard du Maréchal Juin, 14050 Caen, France
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  • Thi-Nhàn Pham,

    1. Laboratoire de Chimie Moléculaire et Thio-organique, ENSICAEN, Université de Caen Basse-Normandie, CNRS; 6 boulevard du Maréchal Juin, 14050 Caen, France
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  • Luc Picton

    1. Polymères, Biopolymères, Membranes UMR 6522 CNRS-Université de Rouen, 76821 Mont Saint Aignan, France
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Abstract

Novel monomers 2-(N-methylacrylamido)ethylphosphonic acid, 6-(N-methylacrylamido)hexylphosphonic acid, 10-(N-methylacrylamido)decylphosphonic acid, and 4-(N-methylacrylamidomethyl)benzylphosphonic acid have been prepared in good yields for use in dental adhesives. They have been fully characterized by 1H-NMR, 13C-NMR, 31P-NMR, and by HRMS. All monomers are hydrolytically stable in aqueous solution. Free radical homopolymerizations of these monomers have been carried out in solution of ethanol/water (2.5/1:v/v), using 2,2′-azo(2-methylpropionamidine) dihydrochloride (AMPAHC) as initiator. They lead to homopolymers in moderate to excellent yields. Structure of the polymers has been confirmed by SEC/MALLS and 1H-NMR spectra. The photopolymerization behavior of the synthesized monomers with N,N′-diethyl-1,3-bis(acrylamido)propane has been investigated by DSC. New self-etch primers, based on these acrylamide monomers, have been formulated. Dentin shear bond strength measurements have shown that primers based on (N-methylacrylamido)alkylphosphonic acids assure a strong bond between the tooth substance and a dental composite. Moreover, the monomer with the longest spacer group provides the highest shear bond strength. © Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 46: 7074–7090, 2008

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