Synthesis, photopolymerization, and adhesive properties of new bisphosphonic acid monomers for dental application

Abstract

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 1 H, 13 C, 31 P 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