Sugar-based surfactants via click chemistry

Abstract

Two new surfactants were synthesized from renewable materials via click chemistry. The starting materials are carbohydrates (e.g. methyl glycoside) and fatty acid derivatives based on both saturated and unsaturated fatty acids with a total chain length of C12 and C18. Target applications of these surfactants focus on the stabilization or emulsions, in particular water-in-oil emulsions. The synthetic scheme applied a multi-step methodology, including activation, functionalization and finally coupling with fatty acids derivatives by using click chemistry technique. Surfactants were identified and their purity confirmed by NMR type 1H and 13C in addition to high resolution mass spectroscopy. Physical properties were studied by optical polarizing microscopy (OPM), differential scanning calorimetry (DSC) and surface tension measurements. Lyotropic phases were investigated by contact penetration with water under the OPM, while surface tension measurements used the DuNouy ring approach. The latter enables the determination of critical micelle concentrations