Synthesis and characterization of the dental adhesive monomer 10-MDP

Abstract

Many studies have demonstrated the excellent performance of 10-MDP (10-methacryloyloxydecyl dihydrogen phosphate) as a functional monomer for dental adhesive materials and as a primer for ceramic surfaces. Although adhesive performance is affected by the purity level of 10-MDP, this parameter is rarely described, and possible byproducts have been suggested in the literature, but have not been identified to date. The present study aims to present an accessible 10-MDP synthesis strategy with easily handled reagents and address the characterization challenges, especially in identifying byproducts. 10-MDP was synthesized from 10-hydroxydecyl methacrylate and phosphorus pentoxide in acetone. The final product was characterized by nuclear magnetic resonance (NMR), infrared spectroscopy (FTIR) and mass spectrometry MALDITOF/TOF. The main chemical groups associated with 10-MDP were identified by ¹H, ³¹P, and ¹³C NMR analyses. Only mass spectrometry analyses (MALDITOF/TOF) could identify the presence of dimers as byproducts. Its proposed chemical structure indicates that the dimers were formed by the reaction between the phosphate ester groups and others formed by the reaction of the methacrylic group of 10-MDP molecules. Careful adjustment of the synthesis conditions to reduce the formation of these byproducts is also described. The results indicate that the characterization of 10-MDP batches as raw materials is an important task because, depending on the byproduct present, its ability to polymerize or acid etching capacity may be compromised.