Aqueous Solution Properties of Disulfide Linked Gemini and Cleaved Monomeric Thiol Surfactants

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  • Asakawa Tsuyoshi
    Division of Material Sciences, Graduate School of Natural Science & Technology, Kanazawa University
  • Shimizu Yasuhiro
    Division of Material Sciences, Graduate School of Natural Science & Technology, Kanazawa University
  • Ozawa Tadahiro
    Division of Material Sciences, Graduate School of Natural Science & Technology, Kanazawa University
  • Ohta Akio
    Division of Material Sciences, Graduate School of Natural Science & Technology, Kanazawa University
  • Miyagishi Shigeyoshi
    Division of Material Sciences, Graduate School of Natural Science & Technology, Kanazawa University

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Abstract

Monomeric thiol surfactants, [CnH2n+1N(CH3)2CH2CH2SH]Br, were produced by the cleavage of gemini surfactant containing a disulfide bond in the spacer chain, [CnH2n+1N(CH3)2CH2CH2SSCH2CH2N(CH3)2CnH2n+1]2Br. The disulfide bond was completely reduced by the addition of four times moles of dithiothreitol in water at room temperature. The critical micelle concentrations of monomeric surfactants were significantly increased in comparison with original gemini surfactants. The monomeric thiol surfactants were stable in the presence of dithiothreitol, whereas they returned gradually to their original gemini surfactants within several days due to air oxidation in water without dithiothreitol. The micelle formation induced by the disulfide linkage formation was suggested by the fluorescence intensity ratio of pyrene. The time course of decrease in thiol concentration associated with the recovery of gemini surfactants was confirmed by the absorption spectra utilizing the reactions with 4,4’-dithiopyridine.<br>

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