Synthesis and characterization of (co)polymers containing a phosphonate function for use in dental composites

Novel monomers 1a, 1b, in which a phosphonate function is incorporated in both aromatic rings, were synthesized from the addition reaction of tetraisopropyl [2,2′-disulfanyl-5,5′-thiodiphenyl]-1,1′-diphosphonate and diisopropyl (2-sulfanylphenyl)-1-phosphonate with the glycidylmethacrylate. Free radical homo- and copolymerizations of phosphonate monomers containing methacrylate groups were first carried out in bulk and in THF solution. They offered (co)polymers for potential use in dental resins, in high yields and moderate to high inherent viscosities. The components and structure of the (co)polymers were confirmed by FTIR, SEC, 1H, 31P NMR spectra. l analysis by using differential scanning calorimetry indicated an amorphous structure of the (co)polymers obtained by polymerization in solution. Upon UV-radiation the composite resins have been synthesized by cross-linking reaction.