N. Moszner, J. Pavlinec, Iris Lamparth
Jul 24, 2006
Citations
0
Influential Citations
28
Citations
Journal
Macromolecular Rapid Communications
Abstract
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, 1 H NMR, 13 C NMR and 31 P 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 °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.