A novel synthetic procedure is described which appears to be an economically attractive route to /V-vinylacetamide (NVA), a monomer capable of yielding a water-soluble polymer of considerable commercial potential. Previously published procedures have been multistep syntheses which gave products requiring considerable purification to obtain monomer quality. The process described involves an initial interchange between acetamide and dimethyl acetal to yield an intermediate ether amide, N-(a-methoxyethylacetamide), which Is then pyrolyzed to give NVA in high yield and high purity. The same procedure was applied to the synthesis of /V-vinylproplonamide. Polymerization of the crude pyrolysate from the above route gave polymer with an inherent viscosity of 1.5 dL/g. Various polymerization conditions were evaluated for the homopolymerization. The homopolymer begins to decompose at 375 °C without melting and could be solvent cast to clear brittle films. Hydrolysis of the homopolymer gave poly(vinylamine). Co polymerization of NVA with vinyl acetate (VA) resulted in copolymers which show a higher NVA content than the monomer mixture. Copolymers with as little as 25 mol % VA had melting points below 100 °C.
r value (r^= 0.01) itself shows microblock structure of the copolymer. This is also reflected in the composition dependence of the clearing temperatures.
AcknowledgmentWe are indepted to Mr. A. Csehi (Gedeon Richter Factory) for the NMR measurements and to Dr. A. Dankovics (our Institute) for the IR measurements and calculations.
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