Abstract
Syntheses of eight novel methacrylates bearing phosphonic acid groups were synthesized in three to five steps. The interaction of these monomers with hydroxyapatite was investigated using 13C-NMR spectroscopy. Free radical homopolymerizations were carried out in a mixture ethanol/water (2.5/1, v/v) using 2,2′azo(2-methylpropionamidine) dihydrochloride as initiator. The copolymerization of these monomers with a mixture HEMA/GDMA (5/3, mol/mol) was investigated by photo-DSC. Dentin shear bond strength measurements showed that 2-methacryloyloxy-3-(1,1,2,2-tetrafluoroethoxy)propylphosphonic acid 4b, 2,3-dimethacryloyloxypropylphosphonic acid 18 and 3-(methacryloyloxy)-2,2-(di[(dihydroxyphosphoryl)methyl])propyl methacrylate 23 are promising candidates for dental adhesives.
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