Monomers for Adhesive Polymers, 6 : Synthesis and Radical Polymerisation of 1,3-Bis(methacrylamido)propane-2-yl Dihydrogen Phosphate

✍ Scribed by Norbert Moszner; Juraj Pavlinec; Iris Lamparth; Frank Zeuner; Jörg Angermann

• Book ID: 102492543
• Publisher: John Wiley and Sons
• Year: 2006
• Tongue: English
• Weight: 256 KB
• Volume: 27
• Category: Article
• ISSN: 1022-1336
• DOI: 10.1002/marc.200600209

✦ Synopsis

Abstract

Summary: 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.

1,3‐Bis(methacrylamido)propane‐2‐yl dihydrogen phosphate.

magnified image1,3‐Bis(methacrylamido)propane‐2‐yl dihydrogen phosphate.