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

Article

Abstract

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 

Abbreviations

C20

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

CMC

critical micelle concentration

MALDI-TOF-MS

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

NDoGI C8Di

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

NMR

nuclear magnetic resonance

RWTH

Rheinisch-Westfälische Technische Hochschule

SEC

sizeexclusion chromatography

TMS

tetramethylsilane

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Kelkenberg, H., Detergentien auf Zuckerbasis, Tenside Surfact. Deterg. 25:8 (1988).Google Scholar
  2. 2.
    van Doren, H.A., Tailor-made Carbohydrate Surfactants? Systematic Investigation into Structure-Property Relationship of N-Acyl N-Alkyl 1-Amino-1-deoxy-d-glucitols, in Carbohydrates as Organic Raw Materials III, edited by H. van Bekkum, H. Röper, and F. Voragen, VCH, Weinheim, 1996, p. 255.Google Scholar
  3. 3.
    Calcott, W.S., and R.G. Clarkson, Chemical Compounds, U.S. Patent 2,060,851 (1935).Google Scholar
  4. 4.
    Kelkenberg, H., Neue N-Alkylglykaminoverbindungen sowie ein Verfahren zur Herstellung und ihre Verwendung, European Patent 0396871 A2 (1990).Google Scholar
  5. 5.
    Warwel, S., F. Brüse, and B. Wiege, Surfactants from Long-Chain N-Alkyl Glucamines and ω-Epoxy Fatty Acid Esters, in Proceedings of Narossa 2002 Magdeburg, published as CD-ROM.Google Scholar
  6. 6.
    Warwel, S., and F. Brüse, Wasserlösliche Tenside auf Basis langkettiger N-Alkylglucamine, in Schriftenreihe “Nachwachsende Rohstoffe,” Nachwachsende Rohstoffe für die Chemie, 8. Symposium 2003 edited by Fachagentur Nachwachsende Rohstoffe, Landwirtschaftsverlag, Münster, 2003, p. 500.Google Scholar
  7. 7.
    Zana, R., Dimeric (gemini) Surfactants, in Novel Surfactants, Preparation, Application, Biodegradability, edited by K. Holmberg, Marcel Dekker, New York, 1998, p. 241.Google Scholar
  8. 8.
    Menger, F.M., and J.S. Keiper, Gemini-Surfactants, Angew. Chem. Int. Ed. Engl. 39:1906 (2000).CrossRefGoogle Scholar
  9. 9.
    Rosen, M.J., and D.J. Tracy, Gemini Surfactants, J. Surfact. Deterg. 1:547 (1998).Google Scholar
  10. 10.
    Krier, V., C. Bassilana, B. Martin, and A. Cambon, Synthesis and Comparison of Highly Fluorinated, Nonionic Surfactants, Tenside Surfact. Deterg. 35:160 (1998).Google Scholar
  11. 11.
    Warwel, S., M. Rüsch gen. Klaas, H. Schier, F. Brüse, and B. Wiege, Surfactants from Glucamines and α-Epoxides, Tenside Surfact. Deterg. 38:7 (2002).Google Scholar
  12. 12.
    Warwel, S., M. Rüsch gen. Klaas, H. Schier, F. Brüse, and B. Wiege, Surfactants from Glucamines and α-Epoxy Fatty Acid Esters, Eur. J. Lipid Sci. Technol. 103:133 (2001).CrossRefGoogle Scholar
  13. 13.
    Warwel, S., F. Brüse, H. Schier, M. Rüsch gen. Klaas, and B. Wiege, Syntheses of Surfactants from Oleochemical Epoxides Oléagineux Corps gras Lipides 8:57 (2001).Google Scholar
  14. 14.
    Warwel, S., and F. Brüse, Sugar-based Surfactants and Functional Sugar Derivatives from Epoxide Ring Opening Reactions with Polyolamines, Fresenius Environ. Bull. 12:540 (2003).Google Scholar
  15. 15.
    Warwel, S., F. Brüse, and B. Wiege, Surfactants from Epoxides and Polyolamines Based on Disaccharides, Tenside Surfact. Deterg. 40:327 (2003).Google Scholar
  16. 16.
    Brüse, F., Tenside Polymerbausteine und Polymere aus Nachwachsenden Rohstoffen Durch Epoxidringöffnungen mit Aminen und enzymatische Polykondensationen, Ph.D. Thesis, Rheinisch-Westfälische Technische Hochschule (RWTH) Aachen, Germany, 2003.Google Scholar
  17. 17.
    Rüsch gen. Klaas, M. and S. Warwel, Lipase-Catalyzed Peroxy Fatty Acid Generation and Lipid Oxidation Properties, in Enzyme in Lipid Modification, edited by U.T. Bornscheuer, Wiley-VCH, Weinheim, 2000, p. 116.CrossRefGoogle Scholar
  18. 18.
    Warwel, S., and M. Rüsch gen. Klaas, New Peroxy-Carboxylic Acids by Lipase Catalysis: Preparation and Oxidation Properties, in Peroxide Chemistry—Mechanistic and Preparative Aspects in Oxygen Transfer, edited by W. Adams, Wiley-VCH, Weinheim, 2000, p. 209.Google Scholar
  19. 19.
    Warwel, S., H. Bachem, A. Deckers, N. Döring, H. Kätker, and E. Rose, Synthesen von Moschus-Riechstoffen Durch Olefin-Metathese, Seifen Öle Fette Wachse 115:538 (1989).Google Scholar
  20. 20.
    Biermanns, F.-J., Metathetische Ethenolyse olefinischer Verbindungen an Re2O7/Al2O3, Ph.D. Thesis, RWTH, Aachen, 1984.Google Scholar
  21. 21.
    Warwel, S., H.G. Jägers, and S. Thomas, Metathese ungesättigter Fettsäureester—Ein einfacher Zugang zu langkettigen Dicarbonsäuren, Fat Sci. Technol. 94:323 (1992).Google Scholar
  22. 22.
    Warwel, S., F. Brüse, C. Demes, M. Kunz, and M. Rüsch gen. Klaas, Polymers and Surfactants on the Basis of Renewable Resources, Chemosphere 43:39 (2001).CrossRefGoogle Scholar
  23. 23.
    Bestimmung der Grenzflächenspannung, Bügel-oder Ringmethode, DIN (German Institute for Norms) 53993 (1984).Google Scholar
  24. 24.
    Bestimmung des Schäumvermögens, DIN (Germany Institute for Norms) 53902-1 (1997).Google Scholar
  25. 25.
    Warwel, S., and F. Brüse, Glucamine-Based Gemini Surfactants II: Gemini Surfactants from Long-Chain N-Alkyl Glucamines and Epoxy Resins, J. Surfact. Deterg. 7, 187–193 (2004).Google Scholar

Copyright information

© AOCS Press 2004

Authors and Affiliations

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

Personalised recommendations