Monomers for Adhesive Polymers, 3. Synthesis, Radical Polymerization and Adhesive Properties of Hydrolytically Stable Phosphonic Acid Monomers

2-(Dihydroxyphosphoryl)ethyloxy-α-methyl-substituted methacrylic acids were synthesized by hydrolyzing ethyl 2-[4-(dihydroxyphosphoryl)-2-oxa-butyl]-acrylate. Methacrylonitrilo- or N,N-diethylmethacrylamido-phosphonic acids were obtained by ether formation of α-chloromethacrylonitrile with hydroxyalkyl phosphonates or aminolysis of 2-[4-(dimethoxyphosphoryl)-2-oxa-butyl]acrylic acid and subsequent hydrolysis to produce the corresponding phosphonic acid. The structure of the new monomers was characterized by IR and by 1H, 13C and 31P 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 different reactivity of the starting radicals. Furthermore, adhesive properties of the phosphonic acid monomers were measured.