Methacrylated calix[4]arene phosphonic acids as functionalized crosslinker for radical polymerization



We describe the synthesis of 5,11,17,23-tetra-tert-butyl-25,27-dioxypropylphosphonic acid-26,28-dimethacryloyloxy-calix [4]arene and 5,11,17,23-tetra-tert-butyl-25-oxypropylphosphonic acid-27-hydroxy-26,28-dimethacryloyloxy-calix[4]arene starting from para-tert-butyl-calix[4]arene. The complete reaction was proved by matrix-assisted laser desorption ionization time of flight mass spectrometry and nuclear magnetic resonance spectroscopy. The influence of these compounds on the kinetics of the radical polymerization of methyl methacrylate was shown by dilatometry. Furthermore, the adhesive properties of dental adhesives containing these calix[4]arene derivatives were investigated. Copyright © 2012 Society of Chemical Industry