Synthesis and interfacial properties of sugar-based surfactants composed of homo- And heterodimers

Journal of Surfactants and Detergents

Volumn 9, Issue 3, 2006, Pages 279-286

  Castro, Mariano J L ^a   Cirelli, Alicia Fernández ^a   Kovensky, José ^b  

^a Universidad de Buenos Aires   (Argentina)

^b UNIVERSITÉ DE PICARDIE JULES VERNE   (France)

Author keywords

Alkyl glucosides; Dimeric amphiphiles; Gemini surfactants; Interfacial properties

Indexed keywords

AMPHIPHILES; GEMINI SURFACTANTS; HETERODIMERS;

DIMERS; INTERFACES (MATERIALS); MIXTURES; SUGARS; SYNTHESIS (CHEMICAL);

SURFACE ACTIVE AGENTS;

EID: 33749459429     PISSN: 10973958     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11743-006-5008-x     Document Type: Article

References (28)

1. Menger, F.M., and J.S. Keiper, Gemini Surfactants, Angew. Chem., Int. Ed. 39:1906 (2000).
2. Zana, R., and J. Xia, Gemini Surfactants, Surfactant Science Series, Vol. 117, Marcel Dekker, New York, 2004.
3. Kirby, A.J., P. Camilleri, J.B.F.N. Engberts, M.C. Feiters, R.J.M. Nolte, O. Söderman, M. Bergsma, P.C. Bell, M.L. Fielden, C.L. Garcia Rodriguez, P. Guédat, A. Kremer, C. McGregor, C. Perrin, G. Ronsin, and M.C.P. van Eijk, Gemini Surfactants: New Synthetic Vectors for Gene Transfection, Angew. Chem., Int. Ed. 42.1448 (2003).
4. Castro, M., D. Griffiths, A. Patel, N. Pattrick, C. Kitson, and M. Ladlow, Effect of Chain Length on Transfection Properties of Spermine-Based Gemini Surfactants, Org. Biomol. Chem. 22814 (2004).
5. Eastoe, J., P. Rogueda, B.J. Harrison, A.M. Howe, and A.R. Pitt, Properties of a Dichained "Sugar Surfactant," Langmuir 10.4429 (1994).
6. van Buuren, A.R., and H.J.C. Berendsen, Molecular Dynamics Simulations of Carbohydrate-Based Surfactants in Surfactant/Water/Oil Systems, Langmuir 10:1703 (1994).
7. Eastoe, J., P. Rogueda, A.M. Howe, A.R. Pitt, and R.K. Heenan, Properties of New Glucamide Surfactants, Langmuir 12:2701 (1996).
8. Pestman, J.M., R. Terpstra, M.C.A. Stuart, H.A. van Doren, A.Brisson, R.M. Kellogg, and J.B.F.N. Engberts, Nonionic Bolaamphiphiles and Gemini Surfactants Based on Carbohydrates, Langmuir 13:6857 (1997).
9. Bergsma, M., M.L. Fielden, and J.B.F.N. Engberts, pH-Dependent Aggregation Behavior of a Sugar-Amine Gemini Surfactant in Water: Vesicles, Micelles, and Monolayers of Hexane 1,6-bis(hexadecyl-1′- deoxyglucitylamine), J. Colloid Interface Sci. 245:491 (2001).
10. Fielden, M.L., C. Perrin, A. Kremer, M. Bergsma, M.C. Stuart, P. Camilleri, and J.B.F.N. Engberts, Sugar-Based Tertiary Amino Gemini Surfactants with a Vesicle-to-Micelle Transition in the Endosomal pH Range Mediate Efficient Transfection in vitro, Eur. J. Biochem. 268:1269 (2001).
11. Wathier, M., A. Polidori, K. Ruiz, A.S. Fabiano, and B. Pucci, Synthèse et étude du comportement en milieu aqueux de tensioactifs gémini glycosylés, New J. Chem. 25:1588 (2001).
12. Menger, F.M., and B.N.A. Nbadugha, Gemini Surfactants with a Disaccharide Spacer, J. Am. Chem. Soc. 123:875 (2001).
13. Hill, K., W. von Rybinski, and G. Stoll, Alkyl Polyglucosides: Technology, Properties and Applications, VCH, Weinheim, 1997.
14. Castro, M.J.L., J. Kovensky, and A. Fernández Cirelli, Gemini Surfactants from Alkyl Glucosides, Tetrahedron Lett. 38:3995 (1997).
15. Castro, M.J.L., J. Kovensky, and A. Fernández Cirelli, New Dimeric Surfactants from Alkyl Glucosides, Tetrahedron 55:12711 (1999).
16. Castro, M.J.L., J. Kovensky, and A. Fernândez Cirelli, Synthesis of New Dimeric Amphiphiles. Influence of Anomeric Configuration and Spacer Functionality on Interfacial Properties, J. Carbohydr. Chem. 12:1175 (2000).
17. Becher, P., Emulsions, Theory and Practice, Litton Educational Publishing, New York, 1965.
18. Fainerman, V.B., and R. Miller, The Maximum Bubble Pressure Tensiometry, in Drops and Bubbles in Interfacial Research, edited by D. Möbius and R. Miller, Elsevier Science, New York, 1998, p. 279.
19. Castro, M.J.L., J. Kovensky, and A. Fernández Cirelli, A Simplified Method for the Determination of Critical Micelle Concentration, J. Chem. Educ. 78:347 (2001).
20. Lide, D.R., CRC Handbook of Chemistry and Physics, CRC Press, Boca Raton, FL, 1997-1998, p. 6.
21. Rosen, M.J., Gemini Surfactants, in New Horizons, edited by R.T. Coffey, Princeton, NJ, 1996.
22. Castro, M.J.L., J. Kovensky, and A. Fernández Cirelli, New Family of Non-ionic Gemini Surfactants. Determination and Analysis of Interfacial Properties, Langmuir 18:2477 (2002).
23. Castro, M.J.L., J. Kovensky, and A. Fernández Cirelli, Synergistic Effects of Alkyl Glucosides and Non-ionic Sugar-Based Gemini Surfactants, Tenside Surf. Det. 39.1 (2002).
24. Rosen, M.J., Surfactants and Interfacial Phenomena, 3rd edn., John Wiley, New York, 2004.
25. Mukerjee, P., The Nature of the Association Equilibria and Hydrophobie Bonding in Aqueous Solutions of Association Colloids, Adv. Colloid Interface Sci. 1:242 (1967).
26. Menger, F.M., and C.A. Littau, Gemini Surfactants: Synthesis and Properties, J. Am. Chem. Soc. 113:1451 (1991).
27. Menger, F.M., and C.A. Littau, Gemini Surfactants: A New Class of Self-assembling Molecules, J. Am. Chem. Soc. 115:10083 (1993).
28. Evans, H.C., Alkyl Sulphates. Part 1. Critical Micelle Concentrations of the Sodium Salts, J. Chem. Soc.:579 (1956).