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

Rudy Covis (1) , Catherine Ladavière (2) , Jacques Desbrieres (3) , Emmanuelle Marie (1) , Alain Durand (1)

1 LCPM - Laboratoire de Chimie Physique Macromoléculaire
2 IMP - Ingénierie des Matériaux Polymères
3 UPPA - Université de Pau et des Pays de l'Adour

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.

Mots clés: Dextran; Amphiphilic polysaccharide; Epoxide; Viscometry

Domaines: Polymères; Matériaux

Rudy Covis, Catherine Ladavière, Jacques Desbrieres, Emmanuelle Marie, Alain Durand. Synthesis of water-soluble and water-insoluble amphiphilic derivatives of dextran in organic medium. Carbohydrate Polymers, 2013, 95 (1), pp.360-365. ⟨10.1016/j.carbpol.2013.03.010⟩. ⟨hal-00867906⟩