Abstract

The synthesis and characterization of new amphiphilic copolymers derived from copolymerization of hydrophobically modified so-called vinyl saccharides with 1-vinyl-2-pyrrolidone are described. The vinyl saccharides were prepared in a two-step synthesis. In the first step hydrophobically modified saccharide derivatives were synthesized without protecting procedures by direct reductive amination of the reducing keto-disaccharide isomaltulose (Palatinose®) with n-dodecylamine. In the second step the resulting N-dodecylaminopolyols were coupled with allyl glycidyl ether to give polymerizable amphiphilic vinyl saccharides. The copolymerizations with 1-vinyl-2-pyrrolidone were performed as free radical aqueous solution polymerizations. The characterization of the copolymers was carried out by measuring the viscosity and light scattering in water as well as in trichloromethane, in addition to surface tension measurements and solubilization studies. The solution properties of the copolymers in water and trichloromethane differ remarkably. While the values for the intrinsic viscosities in both solvents are comparable, the weight-average molecular weights in water are much higher than those in trichloromethane, indicating the formation of aggregates in aqueous solution. The vinyl pyrrolidone copolymers are also very surface active, lowering the surface tension of water to as low as 30 mN/m. The combination of measurements of surface tensions and solubilization studies indicates that their hydrophobic association behaviour is formally comparable to those of low molecular weight surfactants. Keywords: vinyl saccharides, isomaltulose, hydrophobic association, amphiphilic polymers.

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