Synthesis and radical polymerisation of 1,3-bis(methacrylamido)propane-2-yl dihydrogen phosphate

1,3-Bis(methacrylamido)propane-2-yl dihydrogen phosphate (1) was synthesised by phosphorylation of 1,3-bis(methacrylamido)-2-hydroxypropane (2) with phosphorus oxychloride in tetrahydrofuran (THF) in the presence of triethylamine (TEA). The structure of the new monomer 1 was characterised by IR, H-1 NMR, C-13 NMR and P-31 NMR spectroscopies, elemental analysis and mass spectrometry. The monomer dissolves well in water, ethanol or aqueous THF and shows an improved hydrolytic stability compared to the corresponding methacrylate based dihydrogen phosphates. 1 was homopolymerised in ethanol with 2,2'-azoisobutyronitrile (AIBN) as the initiator at 55-75 degrees C under the formation of an insoluble, cross-linked product. Aqueous solutions of 1 are strongly acidic and enable to etch enamel and dentin. Nevertheless, 1 did not show any cytotoxic effect. Furthermore, the adhesive properties of 1 were measured.