Synthèse et copolymérisation d'acrylamides comportant le groupement dihydroxyphosphoryloxyalkyle†

ω-Aminoalkyl dihydrogen phosphates 5a–c, 7 and 9 were obtained in a simple and reproducible fashion by O-phosphorylation of the corresponding aminoalcohols with ClPO3H2 generated in situ by controlled hydrolysis of POCl3. Reaction of these phosphates with acrylic or methacrylic anhydride in water/THF mixture afforded a series of new acrylic monomers (11a–h) bearing a phosphoryl group. Inverted emulsion copolymerization of the latter with the hydrophilic comonomers N-[1,1-bis(hydroxymethyl)-2-hydroxyethyl]acryl- or methacrylamide (12a or 12b) and with the cross-linker N,N′-methylenediacrylamide (13) afforded various gels in the form of spherical beads. Preliminary experiments showed that some of these copolymers could be efficiently used as stationary phases for the separation of proteins by ion-exchange chromatography.