• Picton, Luc
• Catel, Yohann
• Degrange, Michel
• Pluart, Loïc Le
• Pham, Thinhàn
• Madec, Pierrejean

Abstract

<jats:title>Abstract</jats:title><jats:p>Novel monomers 2‐(<jats:italic>N</jats:italic>‐methylacrylamido)ethylphosphonic acid, 6‐(<jats:italic>N</jats:italic>‐methylacrylamido)hexylphosphonic acid, 10‐(<jats:italic>N</jats:italic>‐methylacrylamido)decylphosphonic acid, and 4‐(<jats:italic>N</jats:italic>‐methylacrylamidomethyl)benzylphosphonic acid have been prepared in good yields for use in dental adhesives. They have been fully characterized by <jats:sup>1</jats:sup>H‐NMR, <jats:sup>13</jats:sup>C‐NMR, <jats:sup>31</jats:sup>P<jats:bold>‐</jats:bold>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 <jats:sup>1</jats:sup>H‐NMR spectra. The photopolymerization behavior of the synthesized monomers with <jats:italic>N,N</jats:italic>′‐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 (<jats:italic>N</jats:italic>‐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</jats:p>

Topics

• strength
• composite
• differential scanning calorimetry
• size-exclusion chromatography
• homopolymer
• Nuclear Magnetic Resonance spectroscopy