Nonionic reactive surfactants. I. Synthesis and characterization

A procedure to prepare nonionic reactive surfactants with different polymerizable groups is described. The synthesis involves the initiation of living anionic ring-opening polymerization of ethylene oxide and propylene oxide (for the hydrophilic part and the hydrophobic part, respectively) by a potassium salt prepared from the stoichiometric reaction of potassium hydride and diethylene glycol monomethyl ether. The resulting anion is reacted with chloride compounds (methacryloyl, allyl, vinylacetoyl) and maleic anhydride, as well as with isobutanoyl chloride, leading to a nonpolymerizable compound having a similar structure. Then, it was possible to produce a range of reactive surfactants more or less reactive with the monomers. These surfactants are expected to be used further in emulsion polymerization processes (styrene and butyl acrylate). This procedure gives good control of both hydrophobic and hydrophilic parts, and the end reaction for the different functionality of surfmers is quite quantitative. All the surfactants were characterized by size-exclusion chromatography and 1H NMR. Physicochemical properties, such as the critical micellar concentration and the specific area, were also measured.