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Synthesis and Characterization of New Methacrylic Phosphonated Surface Active Monomer
Author(s) -
Senhaji O.,
Robin J. J.,
Achchoubi M.,
Boutevin B.
Publication year - 2004
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/macp.200400011
Subject(s) - phosphonate , chemistry , polymer chemistry , monomer , alkyl , methyl iodide , organic chemistry , iodide , hydrolysis , alcohol , polymer
Summary: The synthesis of novel methacrylic phosphonated surface‐active monomer by an original method is described. The crucial stage is the telomerization of undec‐10‐enyl acetate with dialkyl (alkyl = methyl or ethyl) hydrogenphosphonate. The phosphonated acetate obtained is selectively hydrolysed to give dialkyl(11‐hydroxyundecyl)phosphonate as a precursor. The alcohol function allows setting of methacrylic side, which is highly reactive in radical polymerization. Particularly, by mono‐dealkylation of dimethyl phosphonate in a selective and quantitative way, the potassium iodide permits to get, at one stage, the expected salt of sodium methyl phosphonate. The new surface‐active sodium methyl(11‐methacryloyloxyundecyl)phosphonate is characterized by 1 H and 31 P NMR. Its critical micelle concentration evaluated by conductometry is 2.4 × 10 −2 mol · l −1 .Synthesis of dialkyl(11‐methacryloyloxyundecyl)phosphonate (DAHP) without protection of alcohol function.