Branched fluorinated amphiphiles based on carbohydrates

Branched fluorinated amphiphiles containing carbohydrate-based hydrophilic groups are presented and compared with traditional poly(ethylene glycol)-based amphiphiles. The carbohydrate and poly(ethylene glycol) groups are grafted onto a hydrophobic block having two or three short, non-bioaccumulative perfluoroalkyl chains by Click Chemistry. The presented amphiphiles containing two perfluoroalkyl chains and 1-desoxy-lactose moiety decrease the static surface tension to below 20 mN/m in water, which is significantly lower than other reported carbohydrate derivatives. Static surface tension is measured by Wilhelmy plate method in aqueous solutions and used to calculate the interfacial packing density. The use of multiple shorter fluorophilic chains into the same surfactant molecule provides comparable surface activity to and circumvents the need for longer fluorinated chains which are banned in several industrial countries for environmental reasons by the year 2015. Hence, the presented amphiphiles are potential alternatives for utilization in e.g. wetting or coating applications. (C) 2013 Elsevier B.V. All rights reserved.