Synthesis of Novel Maleicamido Saccharides and Their Copolymerization with Vinylamides

A new synthesis for anionic unsaturated saccharide monomers from maleic anhydride with amino carbohydrates is described. Various primary and secondary amines with mono and disaccharide moieties were used. The reactions were performed in water at 0°C in the presence of a mineral base, and high yields were achieved. These monomers were found not to be homopolymerizable, but free radical copolymerizations with several N-vinylamides were successfully carried out in water to form a new class of anionic poly(maleicamido saccharide)s (PMAS). As comonomers, N-vinylacetamide (VAA), N-methylvinylacetamide (MVAA) and N-vinylformamide (VFA) were used. In this way linear polyelectrolytes with high average molecular weight could be obtained. The copolymers were characterized by NMR-spectroscopy, IR-spectroscopy, elementary analysis, light scattering, and viscosimetry.