Journal of Surfactants and Detergents

, Volume 7, Issue 2, pp 181–186

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


DOI: 10.1007/s11743-004-0302-1

Cite this article as:
Warwel, S., Brüse, F. & Schier, H. J Surfact Deterg (2004) 7: 181. doi:10.1007/s11743-004-0302-1


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

Diepoxidesepoxide ring-opening reactionsgemini surfactantsglucaminessugar-based surfactants



efficiency=surfactant concentration corresponding to a reduction in surface tension of 20 mN/m in comparison with pure water


critical micelle concentration


matrix-assisted laser/desorption ionization time-of-flight mass spectrometry


1,8-bis(N-dodecyl glucamino-2,7-octanediol


nuclear magnetic resonance


Rheinisch-Westfälische Technische Hochschule


sizeexclusion chromatography



Copyright information

© AOCS Press 2004

Authors and Affiliations

  1. 1.Institute for Lipid ResearchFederal Centre for Cereal Potato and Lipid ResearchMünsterGermany