N. Moszner et al., Monomers for adhesive polymers, 3 - Synthesis, radical polymerization and adhesive properties of hydrolytically stable phosphonic acid monomers, MACRO MAT E, 286(4), 2001, pp. 225-231
2-(Dihydroxyphosphoryl)ethyloxy-alpha -methyl-substituted methacrylic acids
were synthesized by hydrolyzing ethyl 2-[4-(dihydroxyphosphoryl)-2-oxa-but
yl]-acrylate. Methacrylonitrilo- or N,N-diethylmethacrylamido-phosphonic ac
ids were obtained by ether formation of alpha -chloromethacrylonitrile with
hydroxyalkyl phosphonates or aminolysis of 2-[4-(dimethoxyphosphoryl)-2-ox
a-butyl]acrylic acid and subsequent hydrolysis to produce the corresponding
phosphonic acid. The structure of the new monomers was characterized by IR
and by H-1, C-13 and P-31 NMR spectroscopy. The monomers dissolve well in
water and are hydrolytically stable. They demonstrate a different behavior
during radical polymerization in water with 2,2'-azo(2-methylpropionamidine
) dihydrochloride (AMPAHC). This behavior may be attributed to the differen
t reactivity of the starting radicals. Furthermore, adhesive properties of
the phosphonic acid monomers were measured.