Monomers for adhesive polymers: 11. Structure-adhesive properties relationships of new hydrolytically stable acidic monomers

摘要

The synthesis of six new hydrolytically stable acidic monomers is described. Those monomers are AUV-disubstituted acrylamides bearing either a phosphonic acid group or a diphosphonic acid group. They were fully characterized using~1H NMR, ~(13)C NMR and ~(31)P NMR spectroscopy and high-resolution mass spectrometry. The copolymerization of each acidic monomer with N,N'-diethyl-1,3-bis(acrylamido)propane was investigated using photo-differential scanning calorimetry. Self-etching enamel-dentin adhesives were formulated and evaluated in terms of both dentin and enamel adhesion. The influence of the monomer structure (nature of either the spacer or the acidic group, nature of the acrylamide substitution) on the adhesive properties is discussed. The adhesives based on 10-(N-ethylacrylamido)decylphosphonic acid and 10-(N-methylacrylamido)decylbisphosphonic acid are able to achieve a strong bond between a dental composite and both dentin and enamel.