Premium
Monomers for Adhesive Polymers, 3. Synthesis, Radical Polymerization and Adhesive Properties of Hydrolytically Stable Phosphonic Acid Monomers
Author(s) -
Moszner Norbert,
Zeuner Frank,
Pfeiffer Steffen,
Schurte Ivan,
Rheinberger Volker,
Drache Marco
Publication year - 2001
Publication title -
macromolecular materials and engineering
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.913
H-Index - 96
eISSN - 1439-2054
pISSN - 1438-7492
DOI - 10.1002/1439-2054(20010401)286:4<225::aid-mame225>3.0.co;2-t
Subject(s) - monomer , aminolysis , polymer chemistry , polymerization , reactivity (psychology) , materials science , hydrolysis , radical polymerization , methacrylic acid , adhesive , polymer , acrylate , acrylic acid , ether , organic chemistry , chemistry , catalysis , layer (electronics) , medicine , alternative medicine , pathology
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 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.