N. Moszner, F. Zeuner, Steffen Pfeiffer
Apr 1, 2001
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0
Influential Citations
44
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Journal
Macromolecular Materials and Engineering
Abstract
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-(dimethoxyphophoryl)-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 1 H, 13 C and 31 P 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.