Monomers for adhesive polymers, 3 - Synthesis, radical polymerization and adhesive properties of hydrolytically stable phosphonic acid monomers

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.