Startseite Micellar Encapsulation of Some Polycyclic Aromatic Hydrocarbons by Glucose Derived Non-Ionic Gemini Surfactants in Aqueous Medium
Artikel
Lizenziert
Nicht lizenziert Erfordert eine Authentifizierung

Micellar Encapsulation of Some Polycyclic Aromatic Hydrocarbons by Glucose Derived Non-Ionic Gemini Surfactants in Aqueous Medium

  • Lalit Sharma , Saroj und Nirmal Singh
Veröffentlicht/Copyright: 25. September 2014
Veröffentlichen auch Sie bei De Gruyter Brill

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.


* Correspondence address Dr. Lalit Sharma, Department of Applied Chemistry, SBS State Technical Campus, Ferozepur – 152004 India. E-Mail: ; ;

Lalit Sharma is an associate professor at SBS State Technical Campus, Ferozepur (India), and has been working in surfactant science on carbohydrate based surfactants and applications.

Saroj is senior research fellow at SBS State Technical Campus who is working in surfactant science.

Nirmal Singh is junior research fellow at SBS State Technical Campus who is working in surfactant science.


References

1. Bunton, C. A., Robinson, L. B., Schaak, J. and Stam, M. F.: J. Org. Chem.36 (1971) 2346. DOI: 10.1021/jo00806a006Suche in Google Scholar

2. Menger, M. F. and Littau, C. A.: J. Am. Chem. Soc.115 (1993) 10083. DOI: 10.1021/ja00062a086Suche in Google Scholar

3. Zana, R. and Talmon, Y.: Nature362 (1993) 228. DOI: 10.1038/362228a0Suche 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_4Suche in Google Scholar

5. Rosen, M. J.: Chemtech23 (1993) 30.Suche 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-QSuche in Google Scholar

7. Bombelli, C., Giansanti, L., Luciani, P. and Mancini, G.: Curr. Med. Chem.16 (2009) 171. DOI: 10.2174/092986709787002808Suche 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.ch29Suche in Google Scholar

9. Han, Y. and Wang, Y.: Phys. Chem. Chem. Phys.13 (2011) 1939. DOI: 10.1039/c0cp01196gSuche in Google Scholar

10. Sakai, K., Sakai, H. and Abe, M.: J. Oleo Sci.60 (2011) 159. DOI: 10.5650/jos.60.159Suche in Google Scholar

11. Sharma, V. D. and Llies, M. A.: Med. Res. Revs. (2012). DOI: 10.1002/med.21272Suche in Google Scholar

12. Sharma, L. and Singh, S.: Carbohydr. Res.270 (1995).Suche 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)00817-4Suche in Google Scholar

14. Castro, M. J. L., Kovensky, J. and Cirelli, A. F.: Tetrahedron55 (1997) 12711. DOI: 10.1016/S0040-4020(99)00786-3Suche in Google Scholar

15. Castro, M. J. L., Kovensky, J. and Cirelli, A. F.: Molecules5 (2000) 608. DOI: 10.3390/50300424Suche in Google Scholar

16. Castro, M. J. L., Kovensky, J. and Cirelli, A. F.: Langmuir18 (2002) 2477. DOI: 10.1021/la001549eSuche in Google Scholar

17. Castro, M. J. L., Kovensky, J. and Cirelli, A. F.: Arkivoc12 (2005) 252.Suche 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/s11743-999-0080-9Suche 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)00038-1Suche in Google Scholar

20. Menger, F. M. and Mbadugha, B. N. A.: J. Am. Chem. Soc.123 (2001) 875. DOI: 10.1021/ja0033178Suche 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/la970681kSuche 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.xSuche 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-zSuche in Google Scholar

24. Komorek, U. and WilkK.A.: J. Colloid Interface Sci.271 (2004) 206. DOI: 10.1016/j.jcis.2003.09.020Suche in Google Scholar PubMed

25. Warwel, S., Brüse, F. and Schier, H.: J. Surf. Deterg.7 (2004) 181. DOI: 10.1007/s11743-004-0302-1Suche in Google Scholar

26. Warwel, S., Brüse, F. and Schier, H.: J. Surf. Deterg.7 (2004) 187. DOI: 10.1007/s11743-004-0302-1Suche in Google Scholar

27. Han, F. and Zhang, G.: J. Surf. Deterg.7 (2004) 175. DOI: 10.1007/s11743-004-0301-2Suche 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.2003.12.006Suche in Google Scholar PubMed

29. Yoshimura, T., Ishihara, K. and Esumi, K.: Langmuir21 (2005) 10409. DOI: 10.1021/la047773bSuche in Google Scholar PubMed

30. Laska, U., Wilk, K. A., Maliszewska, I. and Syper, L.: J. Surf. Deterg.9 (2006) 115. DOI: 10.1007/s11743-006-0380-0Suche in Google Scholar

31. Wagenaar, A. and Engberts, J. B. F. N.: Tetrahdron63 (2007) 10622. DOI: 10.1016/j.tet.2007.08.023Suche 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.2008.06.033Suche 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.2007.10.039Suche 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/jo9018107Suche 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.2011.02.011Suche 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.2012.07.014Suche in Google Scholar

37. Sharma, L. and Saroj: J. Incl. Phenom. Macrocycl. Chem.74 (2012) 251. DOI: 10.1007/s10847-012-0107-ySuche in Google Scholar

38. Laher, J. M. and Barrowman, J. A.: Lipids18 (1983) 218. DOI: 10.1007/BF02534551Suche in Google Scholar PubMed

39. Ohle, H. and Vargha, L. v.: Berichte62 (1929) 2435.Suche in Google Scholar

40. Gratzer, W. B. and Beaven, G. H.: J. Phys. Chem.73 (1969) 2270. DOI: 10.1021/j100727a028Suche in Google Scholar PubMed

41. Parker, R. E. and Issacs, N. S.: Chem. Rev.59 (1959) 737. DOI: 10.1021/cr50028a003Suche 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/v72-307Suche in Google Scholar

43. Vyas, D. M., Jarrell, H. C. and Szarek, W. A.: Can. J. Chem.53 (1975) 2748. DOI: 10.1139/v75-188Suche in Google Scholar

44. Griffin, W. C.: J. Soc. Cosmet. Chemists5 (1954) 249.Suche in Google Scholar

Received: 2013-08-15
Revised: 2013-10-27
Published Online: 2014-09-25
Published in Print: 2014-09-15

© 2014, Carl Hanser Publisher, Munich

Heruntergeladen am 9.10.2025 von https://www.degruyterbrill.com/document/doi/10.3139/113.110327/html?lang=de
Button zum nach oben scrollen