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

Abstract

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 1 H‐NMR, 13 C‐NMR, 31 P ‐ 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 1 H‐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