Micellar Encapsulation of Some Polycyclic Aromatic Hydrocarbons by Glucose Derived Non-Ionic Gemini Surfactants in Aqueous Medium
-
Lalit Sharma
Abstract
Novel glucose-based non-ionic gemini surfactants consisting of two sugar head groups, two hydrophobic tails having chain length of C8, C10, C12, C14, C16, C18 and –CH2-C6H4-CH2– as a rigid spacer were synthesized and investigated for their micellar encapsulation properties. The head groups of the geminis consist of glucose entities (with reducing function blocked in cyclic acetal group) connected through C-6 to tertiary amines. These surfactants were explored for micellar encapsulation of some polynuclear aromatic hydrocarbons (PAHs) viz. fluorene, anthracene, triptycene and pyrene in 20% ethanol–water mixture. Micellar studies revealed that PAHs were encapsulated in the sequence fluorene > anthracene > triptycene > pyrene and the better efficiency of gemini surfactant was dependent on longer alkyl tail but lesser HLB value.
Kurzfassung
Neue, auf Glukose basierende, nichtionische Gemini-Tenside wurden synthetisiert und hinsichtlich ihrer mizellaren Verkapselung untersucht. Die neuen Gemini-Tenside bestehen aus zwei Zucker-Kopfgruppen und zwei hydrophoben Alkylketten der Längen C8, C10, C12, C14, C16, C18, die über einen –CH2-C6H4-CH2– -Spacer verbunden sind. Die Kopfgruppen der Gemini-Tenside bestehen aus Glucose-Einheiten (mit reduzierter Funktion blockiert in der cyclischen Acetal-Gruppe), die über C-6 an die tertiären Amine gebunden sind. Diese Tenside wurden untersucht hinsichtlich der Verkapselung von bestimmten polyzyklischen aromatischen Kohlenwasserstoffen [PAKs] (Fluoren, Anthracen, Triptycen und Pyren) in Mizellen aus einer wässrigen Lösung mit 20% Ethanol. Die PAKs ließen sich in der Reihenfolge Fluoren > Anthracen > Triptycen > Pyren verkapseln. Die höhere Wirksamkeit der Gemini-Tenside hing mehr von der Länge der Alkylketten ab als von dem geringeren HLB-Wert.
References
1. Bunton, C. A., Robinson, L. B., Schaak, J. and Stam, M. F.: J. Org. Chem.36 (1971) 2346. DOI: 10.1021/jo00806a006Search in Google Scholar
2. Menger, M. F. and Littau, C. A.: J. Am. Chem. Soc.115 (1993) 10083. DOI: 10.1021/ja00062a086Search in Google Scholar
3. Zana, R. and Talmon, Y.: Nature362 (1993) 228. DOI: 10.1038/362228a0Search in Google Scholar
4. Zana, R.: Specialist surfactants. in: Robb, I. D., (Ed.): Chapman Hall Ltd., London (1996) 81.10.1007/978-94-009-1557-2_4Search in Google Scholar
5. Rosen, M. J.: Chemtech23 (1993) 30.Search in Google Scholar
6. Menger, F. M. and Keiper, J. S.: Angew. Chem. Int. Ed. Engl.39 (2000) 1906. DOI: 10.1002/1521-3773(20000602)39:11<1906::AID-ANIE1906>3.0.CO;2-QSearch in Google Scholar
7. Bombelli, C., Giansanti, L., Luciani, P. and Mancini, G.: Curr. Med. Chem.16 (2009) 171. DOI: 10.2174/092986709787002808Search in Google Scholar
8. Mbadugha, B. N. A. and Keiper, J. S.: In: Handbook of detergents/part F: Production. Taylor & Francis Group LLC, Philadelphia. (2009) 561.10.1201/9781420014655.ch29Search in Google Scholar
9. Han, Y. and Wang, Y.: Phys. Chem. Chem. Phys.13 (2011) 1939. DOI: 10.1039/c0cp01196gSearch in Google Scholar
10. Sakai, K., Sakai, H. and Abe, M.: J. Oleo Sci.60 (2011) 159. DOI: 10.5650/jos.60.159Search in Google Scholar
11. Sharma, V. D. and Llies, M. A.: Med. Res. Revs. (2012). DOI: 10.1002/med.21272Search in Google Scholar
12. Sharma, L. and Singh, S.: Carbohydr. Res.270 (1995).Search in Google Scholar
13. Castro, M. J. L., Kovensky, J. and Cirelli, A. F.: Tet. Lett.38 (1997) 3995. DOI: 10.1016/S0040-4039(97)00817-4Search in Google Scholar
14. Castro, M. J. L., Kovensky, J. and Cirelli, A. F.: Tetrahedron55 (1997) 12711. DOI: 10.1016/S0040-4020(99)00786-3Search in Google Scholar
15. Castro, M. J. L., Kovensky, J. and Cirelli, A. F.: Molecules5 (2000) 608. DOI: 10.3390/50300424Search in Google Scholar
16. Castro, M. J. L., Kovensky, J. and Cirelli, A. F.: Langmuir18 (2002) 2477. DOI: 10.1021/la001549eSearch in Google Scholar
17. Castro, M. J. L., Kovensky, J. and Cirelli, A. F.: Arkivoc12 (2005) 252.Search in Google Scholar
18. Gao, C., Millqvist-Fureby, A., Whitcombe, M. J. and Vulfson, E. N.: J. Surf. Deterg.2 (1999) 293. DOI: 10.1007/s11743-999-0080-9Search in Google Scholar
19. Gao, C., Millqvist-Fureby, A., Whitcombe, M. J. and Vulfson, E. N.: Enzym. Microb. Technol.25 (1999) 264. DOI: 10.1016/S0141-0229(99)00038-1Search in Google Scholar
20. Menger, F. M. and Mbadugha, B. N. A.: J. Am. Chem. Soc.123 (2001) 875. DOI: 10.1021/ja0033178Search in Google Scholar PubMed
21. Pestman, J. M., Terpstra, R., Stuart, M. C. A., van Doren, H. A., Brisson, A., Kellogg, R. M. and Engberts, J. B. F. N.: Langmuir13 (1997) 6857. DOI: 10.1021/la970681kSearch in Google Scholar
22. Fielden, M. L., Perrin, C., Kremer, A., BergsmaM., Stuart, M. C., Camilleri, P. and Engberts, J. B. F. N.: Eur J. Biochem.268 (2001) 1269. DOI: 10.1046/j.1432-1327.2001.01995.xSearch in Google Scholar PubMed
23. Wilk, K. A., Syper, L., Domagalska, B. W., Laska, U., Maliszewska, I. and Gancarz, R.: J. Surf. Deterg.5 (2002) 235. DOI: 10.1007/s11743-002-0223-zSearch in Google Scholar
24. Komorek, U. and WilkK.A.: J. Colloid Interface Sci.271 (2004) 206. DOI: 10.1016/j.jcis.2003.09.020Search in Google Scholar PubMed
25. Warwel, S., Brüse, F. and Schier, H.: J. Surf. Deterg.7 (2004) 181. DOI: 10.1007/s11743-004-0302-1Search in Google Scholar
26. Warwel, S., Brüse, F. and Schier, H.: J. Surf. Deterg.7 (2004) 187. DOI: 10.1007/s11743-004-0302-1Search in Google Scholar
27. Han, F. and Zhang, G.: J. Surf. Deterg.7 (2004) 175. DOI: 10.1007/s11743-004-0301-2Search in Google Scholar
28. Mine, Y., Fukunaga, K., Samejima, K., Yoshimoto, M., Nakao, K. and Sugimura, Y.: Carbohydr. Res.339 (2004) 493. DOI: 10.1016/j.carres.2003.12.006Search in Google Scholar PubMed
29. Yoshimura, T., Ishihara, K. and Esumi, K.: Langmuir21 (2005) 10409. DOI: 10.1021/la047773bSearch in Google Scholar PubMed
30. Laska, U., Wilk, K. A., Maliszewska, I. and Syper, L.: J. Surf. Deterg.9 (2006) 115. DOI: 10.1007/s11743-006-0380-0Search in Google Scholar
31. Wagenaar, A. and Engberts, J. B. F. N.: Tetrahdron63 (2007) 10622. DOI: 10.1016/j.tet.2007.08.023Search in Google Scholar
32. Takamatsu, Y., Torigue, K., Yoshimura, T., Esumi, K., Sakai, H. and Abe, M.: Colloids Surface A328 (2008) 100. DOI: 10.1016/j.colsurfa.2008.06.033Search in Google Scholar
33. Sakai, K., Umezawa, S., Tamura, M., Takamatsu, Y., Tsuchiya, K., Torigoe, K., Ohkubo, T., Yoshimura, T., Tsumi, K., Sakai, H. and Abe, M.: J. Colloid Interface Sci.318 (2008) 440. DOI: 10.1016/j.jcis.2007.10.039Search in Google Scholar PubMed
34. Jahan, N., Paul, N., Petropolis, C. J., Marangoni, D. G. and Grindley, T. B.: J. Org. Chem.74 (2009) 7762. DOI: 10.1021/jo9018107Search in Google Scholar PubMed
35. Wilk, K. A., Laska, U., Zieliński, K. and Olszowski, A.: Photochem. Photobiol. A. Chem.219 (2011) 204. DOI: 10.1016/j.jphotochem.2011.02.011Search in Google Scholar
36. Mohammed, A. I., Abboud, Z. H. and Alghanimi, A. H. O.: Tet. Lett.53 (2012) 5081. DOI: 10.1016/j.tetlet.2012.07.014Search in Google Scholar
37. Sharma, L. and Saroj: J. Incl. Phenom. Macrocycl. Chem.74 (2012) 251. DOI: 10.1007/s10847-012-0107-ySearch in Google Scholar
38. Laher, J. M. and Barrowman, J. A.: Lipids18 (1983) 218. DOI: 10.1007/BF02534551Search in Google Scholar PubMed
39. Ohle, H. and Vargha, L. v.: Berichte62 (1929) 2435.Search in Google Scholar
40. Gratzer, W. B. and Beaven, G. H.: J. Phys. Chem.73 (1969) 2270. DOI: 10.1021/j100727a028Search in Google Scholar PubMed
41. Parker, R. E. and Issacs, N. S.: Chem. Rev.59 (1959) 737. DOI: 10.1021/cr50028a003Search in Google Scholar
42. Hall, L. D., Black, S. A., Seessor, K. N. and Tracey, A. S.: Can. J. Chem.50 (1972) 1912. DOI: 10.1139/v72-307Search in Google Scholar
43. Vyas, D. M., Jarrell, H. C. and Szarek, W. A.: Can. J. Chem.53 (1975) 2748. DOI: 10.1139/v75-188Search in Google Scholar
44. Griffin, W. C.: J. Soc. Cosmet. Chemists5 (1954) 249.Search in Google Scholar
© 2014, Carl Hanser Publisher, Munich
Articles in the same Issue
- Contents/Inhalt
- Contents
- Abstracts
- Abstracts
- Special Theme: Green Surfactants – Synthesis, Properties, Performance and Application
- Novel Cationic Gemini Surfactants and Methods for Determination of Their Antimicrobial Activity – Review
- Sophorolipids Synthesized Using Non-Traditional Oils with Glycerol and Studies on Their Surfactant Properties with Synthetic Surfactant
- Rhamnolipids Production by a Pseudomonas eruginosa LBI Mutant: Solutions and Homologs Characterization
- Application of Biosurfactant Surfactin on Copper Ion Removal from Sand Surfaces with Continuous Flushing Technique
- Synthesis and Properties of a Series of CO2 Switchable Gemini Imidazolium Surfactants
- Phase Behavior and Solubilization of Microemulsion Systems Containing Imidazolium Type Surfactant CnmimBr and Butyric Acid as Cosurfactant
- Synthesis and Solution Properties of New Polysiloxane Bola Surfactants Containing Carbohydrate
- Syntheses and Properties of Novel Ionic Twin-tail Trisiloxane Surfactants
- Micellar Encapsulation of Some Polycyclic Aromatic Hydrocarbons by Glucose Derived Non-Ionic Gemini Surfactants in Aqueous Medium
- Environmental Chemistry
- Removal of Non-Ionic Surfactants in an Activated Sludge Sewage Treatment Plant
- Cleaning Technology
- Impact of Artificial UV-Light on Optical and Protective Effects of Cotton After Washing with Detergent Containing Fluorescent Compounds
- Simulating Consumer-Like Air Drying of Dishes via Thermal Drying Process
Articles in the same Issue
- Contents/Inhalt
- Contents
- Abstracts
- Abstracts
- Special Theme: Green Surfactants – Synthesis, Properties, Performance and Application
- Novel Cationic Gemini Surfactants and Methods for Determination of Their Antimicrobial Activity – Review
- Sophorolipids Synthesized Using Non-Traditional Oils with Glycerol and Studies on Their Surfactant Properties with Synthetic Surfactant
- Rhamnolipids Production by a Pseudomonas eruginosa LBI Mutant: Solutions and Homologs Characterization
- Application of Biosurfactant Surfactin on Copper Ion Removal from Sand Surfaces with Continuous Flushing Technique
- Synthesis and Properties of a Series of CO2 Switchable Gemini Imidazolium Surfactants
- Phase Behavior and Solubilization of Microemulsion Systems Containing Imidazolium Type Surfactant CnmimBr and Butyric Acid as Cosurfactant
- Synthesis and Solution Properties of New Polysiloxane Bola Surfactants Containing Carbohydrate
- Syntheses and Properties of Novel Ionic Twin-tail Trisiloxane Surfactants
- Micellar Encapsulation of Some Polycyclic Aromatic Hydrocarbons by Glucose Derived Non-Ionic Gemini Surfactants in Aqueous Medium
- Environmental Chemistry
- Removal of Non-Ionic Surfactants in an Activated Sludge Sewage Treatment Plant
- Cleaning Technology
- Impact of Artificial UV-Light on Optical and Protective Effects of Cotton After Washing with Detergent Containing Fluorescent Compounds
- Simulating Consumer-Like Air Drying of Dishes via Thermal Drying Process
