Oleic Acid-Based Gemini Surfactants with Carboxylic Acid Headgroups

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  • Sakai Kenichi
    Department of Pure and Applied Chemistry, Faculty of Science and Technology, Tokyo University of Science
  • Umemoto Naoki
    Department of Pure and Applied Chemistry, Faculty of Science and Technology, Tokyo University of Science
  • Matsuda Wataru
    Department of Pure and Applied Chemistry, Faculty of Science and Technology, Tokyo University of Science
  • Takamatsu Yuichiro
    Miyoshi Oil & Fat Co., Ltd.
  • Matsumoto Mutsuyoshi
    Department of Materials Science and Engineering, Faculty of Industrial Science and Technology, Tokyo University of Science
  • Sakai Hideki
    Department of Pure and Applied Chemistry, Faculty of Science and Technology, Tokyo University of Science
  • Abe Masahiko
    Department of Pure and Applied Chemistry, Faculty of Science and Technology, Tokyo University of Science

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Anionic gemini surfactants with carboxylic acid headgroups have been synthesized from oleic acid. The hydrocarbon chain is covalently bound to the terminal carbonyl group of oleic acid via an ester bond, and the carboxylic acid headgroups are introduced to the cis double bond of oleic acid via disuccinyl units. The surfactants exhibit pH-dependent protonation–deprotonation behavior in aqueous solutions. In alkaline solutions (pH 9 in the presence of 10 mmol dm–3 NaCl as the background electrolyte), the surfactants can lower the surface tension as well as form molecular assemblies, even in the region of low surfactant concentrations. Under acidic (pH 3) or neutral (pH 6–7) conditions, the surfactants are intrinsically insoluble in aqueous media and form a monolayer at the air/water interface. In this study, we have investigated physicochemical properties such as the function of the hydrocarbon chain length by means of static surface tension, pyrene fluorescence, dynamic light scattering, surface pressure–area isotherms, and infrared external reflection measurements.

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