Synthesis of water-soluble and water-insoluble amphiphilic derivatives of dextran in organic medium

Hydrophobically modified dextrans were prepared by reacting native polysaccharide with 1,2-epoxydodecane in dimethylsulfoxide. Epoxide oligomerization was shown to occur as a secondary reaction when hydroxide ions were used as base catalysts. By adjusting the amount of epoxide in the feed, dextran derivatives with degrees of substitution (DS) between 0% and 164% were obtained. Polymers with DS above 100% were readily soluble in organic solvents like tetrahydrofuran, dioxane and water-saturated chloroform and dichloromethane. Their solution properties in organic solvent were characterized by capillary viscometry. Water-soluble derivatives were compared to other amphiphilic dextrans obtained using a heterogeneous modification in aqueous medium. The effect of modification conditions on substitution pattern was evidenced.