Synthesis of non-ionic water-soluble cellulose derivatives with low degrees of substitution via the Michael addition reaction

Abstract This study investigates the Michael addition of cotton cellulose to N-(2-hydroxyethyl)acrylamide (HEAA) as an electrophile in the presence of LiOH in ionic liquid (1-butyl-2,3-dimethylimidazolium chloride)/DMF solvents at 40 to 60 oC for 12 or 24 h to synthesize new non-ionic cellulose derivatives; that is, cellulosic Michael adducts with N-(2-hydroxyethyl)propionamido substituents. As the products were totally or even partly soluble in water, depending on the reaction conditions, the 1H NMR analysis was conducted in a D2O solvent to suggest their low degrees of substitution (0.58 to 0.91).