Journal of Surfactants and Detergents

, Volume 7, Issue 2, pp 187–193

Glucamine-based gemini surfactants II: Gemini surfactants from long-chain N-alkyl glucamines and epoxy resins


DOI: 10.1007/s11743-004-0303-0

Cite this article as:
Warwel, S. & Brüse, F. J Surfact Deterg (2004) 7: 187. doi:10.1007/s11743-004-0303-0


Gemini surfactants were synthesized by reaction of long-chain N-alkyl glucamines with epoxy resins. Analogous to the synthesis of gemini surfactns from long-chain N-alkyl glucamines and α, ω-diepoxides (1), the reaction in methanol at 70°C could be used to convert the starting materials selectively and almost quantitatively. N-Octyl glucamine, N-decyl glucamine, and N-dodecyl glucamine were combined with several epoxy resins, mainly technical glycidyl ethers of diols. Syntheses involving equimolar amounts of amine resulted in quantitative conversion of the epoxy resins, and epoxide and products could be isolated quantitatively by removing the solvent. Gemini surfactants having hydrophobic or hydrophilic spacers were preparared according to their structures and the hydrophilic properties of the epoxy resin. Surface tensions were measured, and foaming propertiers were examined to characterize surface-active properties of these surfactants. The more hydrophilic products were of particularly high surface activity. Tensiometric studies showed a reduction of surface tension to 30–34 mN/m and critical micelle concentrations in the range of 2–35 mg/L. Comparison of gemini surfactants from long-chain N-alkyl glucamines and diepoxides of α,ω-diolefins (chain lengths: C8, C9, C10, and C14) with those based on epoxy resins showed similar or lower surface activities using hydrophobic epoxy resins and much better surface-active properties using hydrophilic epoxy resins (e.g., based on glycerol). This, together with the easier availability, makes the epoxy resin-based products interesting surfactants. Products having very good surface-active properties are available, especially using glycidyl ether of aliphatic diols or glycerol.

Key Words

Epoxy resinsgemini 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


size-exclusion chromatography

Copyright information

© AOCS Press 2004

Authors and Affiliations

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