Journal of Surfactants and Detergents

, Volume 7, Issue 2, pp 181-186

First online:

Glucamine-based gemini surfactants I: Gemini surfactants from long-chain N-alkyl glucamines and α,ω-diepoxides

  • S. WarwelAffiliated withInstitute for Lipid Research, Federal Centre for Cereal Potato and Lipid Research Email author 
  • , F. Brüse
  • , H. SchierAffiliated withInstitute for Lipid Research, Federal Centre for Cereal Potato and Lipid Research

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N-Alkyl glucamines can be reacted with α,ω-diepoxides to yield gemini (dimeric) surfactants similarly to the reaction of glucamine with terminal epoxides. Under the conditions chosen for this work, epoxides were quantitatively converted in the presence of an equimolar amount of amine to gemini surfactants. Reactions could be carried out under mild conditions (70°C) in methanol, and products were obtained quantitatively by removing the solvent. The combination of N-octyl glucamine, N-decyl glucamine, or N-dodecyl glucamine with diepoxides of α,ω-diolefins having chain lengths of C8, C9, C10, or C14 resulted in gemini surfactants differing in spacer length and length of hydrophobic alkyl chains. Surface-active properties were studied by measuring surface tension and evaluating foaming properties. Tensiometric studies showed the reduction of surface tension down to 29–33 mN/m and critical micelle concentrations often in the range of 3–150 mg/L. Comparison of a selected gemini surfactant [1,8-bis(N-dodecyl glucamino-2,7-octane diol] with its corresponding “single surfactant” demonstrated the enhancement of surface-active properties afforded by the gemini structure.

Key words

Diepoxides epoxide ring-opening reactions gemini surfactants glucamines sugar-based surfactants