Synthesis, Photopolymerization, and Adhesive Properties of Hydrolytically Stable Phosphonic Acid-Containing (Meth)acrylamides

Three novel dental monomers containing phosphonic acid groups (1a and 2a, based on diethyl amino(phenyl)methylphosphonate and 3a based on diethyl 1-aminoheptylphosphonate) were synthesized in two steps: the reaction of -aminophosphonates with acryloyl chloride (for monomers 1a and 3a) or methacryloyl chloride (for 2a) to give monomers with phosphonate groups, and the hydrolysis of phosphonate groups by using trimethyl silylbromide. Their (and the intermediates') structures were confirmed by FTIR, H-1, C-13, and P-31 NMR spectroscopy. All the monomers dissolve well in water (1