Synthesis and preliminary assessments of hybrid hydrocarbon–fluorocarbon anionic and non-ionic surfactants

We describe the synthesis and preliminary physico-chemical assessments of ionic and non-ionic hybrid hydrofluorocarbon amphiphiles. Monoreduction reaction of the symmetrical starting material 1,10-diiodo-3,3,4,4,5,5,6,6,7,7,8,8-dodecafluorodecane provides the ethyl terminated fluorocarbon chains. These non-symmetrical hydrofluorocarbon surfactants contain an ethyl segment, a fluorocarbon core and either nonionic or anionic polar heads (sulfate, sulfonate, phosphate, carboxylate or glycosidic groups). The lactobionolactone can be reacted with hydrofluorocarbon amines to obtain the non-ionic hydrophilic moiety whereas the anionic heads come from monoiodo and/or hydroxyl hydrofluorocarbon substrates. The critical micellar concentration (CMC) values of these novel surfactants were determined by surface tension and conductivity measurements. The results are compared to those measured with fluorinated homologues previously described.