Accessible Requires Authentication Published by De Gruyter September 9, 2013

Novel Diphenyl Methane Based Quaternary Ammonium Surfactants: Synthesis, Surface Properties and Antimicrobial Activity

Neuartige quaternäre Diphenylmethanammoniumtenside: Synthese, Oberflächeneigenschaften und antimikrobielle Aktivitäten
Tawfik M. Kassem, Abdallah A. El-Sawy, Ammona S. Mohamed, Dalia E. Mohamed and Fatma M. Abdelhafiz

Abstract

A homologous series of cationic gemini diphenyl methane quaternary ammonium salts have been synthesized via chloromethylation of diphenyl methane followed by quaternization using tertiary amines with different chain length. The chemical structures of the prepared surfactants were confirmed using different spectroscopic techniques including, FTIR and 1H-NMR spectra. Surface activity of these compounds have been thoroughly studied and their surface properties including surface and interfacial tension, emulsification power, critical micelle concentration, effectiveness, efficiency, maximum surface excess and minimum surface area were determined. The new synthesized surfactants were screened as antimicrobial agents against different strains of bacteria, yeast and fungi.

Kurzfassung

Eine homologe Reihe kationischer, quaternärer Diphenylmethanammoniumtenside wurde über die Chlormethylierung von Diphenylmethan und nachfolgender Quaternierung mit tertären Aminen unterschiedlicher Kettenlänge synthetisiert. Die chemischen Strukturen der synthetisierten Geminitenside wurden mit Hilfe verschiedener spektroskopischer Verfahren wie FTIR und 1H-NMR bestätigt. Die Oberflächenaktivität dieser Verbindungen wurde sorgfältig untersucht und die Oberflächeneigenschaften dieser Tenside wie die Oberflächen- und Grenzflächenspannung, das Emulgiervermögen, die kritische Mizellbildungskonzentration, die Wirkung und Leistungsfähigkeit, der maximale Oberflächenüberschuss und der minimale Platzbedarf an der Oberfläche wurden bestimmt. Die antimikrobielle Wirkung der synthetisierten Tenside gegen verschiedene Bakterienstämme, Hefen und Pilze wurde getestet.


1 Dr. Dalia Emam Mohamed, Surface Active Agents Lab. Egyptian Petroleum Research Institute (EPRI)1 Ahmed El-Zomor Street El-Zohour Region Nasr City – Cairo Egypt, E-Mail:

Tawfik M. Kassem was received his B.Sc. from Ain Shams University (1964), M.Sc. from Cairo University (1968) and Ph.D. from Ain Shams University (1973). He is Professor of Petrochemicals in the Petrochemicals Department (Egyptian Petroleum Research Institute, EPRI). His interests are focused on the synthesis and evaluations of surfactants in several fields including, biocidal application and solubilization.

Abdallah A. El-Sawy has a Ph.D. in Organic Chemistry, and is currently Professor of Organic Chemistry at Benha University, Benha City, Egypt. His research interests are in surfactants science and applications.

Ammona S. Mohamed was received her B.Sc. and M.Sc. from the Suez Canal University and her Ph.D. from Ain Shams University (2000). She is presently Professor of Applied Surfactants in the Petrochemicals Department (Egyptian Petroleum Research Institute, EPRI). Her interests are focused on the synthesis and evaluations of surfactants in several fields including, biocidal application, solubilization, and antitumor activity.

Dalia E. Mohamed was received her B.Sc. and M.Sc. from Cairo University and Ph.D. from Ain Shams University. She is currently researcher at the Egyptian Petroleum Research Institute (Surfactants Laboratory). Her research interests are in synthesis, properties and applications of new surfactants.

Fatma M. Abdelhafiz was received her B.Sc. from Ain Shams University (2006). She is currently specialist at the Egyptian Petroleum Research Institute (Surfactants Laboratory). Her interests are focused on synthesis, properties and applications of new surfactants in several fields.


References

1. Rist, Ø., Rike, A., Ljones, L. and Carlsen, P. H. J.: Molecules6 (2001) 979987. Search in Google Scholar

2. Menger, F. M. and Littau, C. A.: J. Am. Chem. Soc.113 (1991) 1451. Search in Google Scholar

3. Menger, F. M. and Keiper, J. S.: Angew. Chem., Int. Ed.39 (2000) 1906. Search in Google Scholar

4. Zana, R.: Adv. Colloid Interface Sci.97 (2002) 205. Search in Google Scholar

5. Pisarčik, M., Rosen, M. J., Polakovičova, M., Devinsky, F. and Lacko, I.: J. Colloid. Interface Sci.289 (2005) 560. Search in Google Scholar

6. Wang, Y. X., Han, Y. C., Huang, X., Cao, M. W. and Wang, Y. L.: J. Colloid. Interface Sci.319 (2008) 534. Search in Google Scholar

7. Oda, R., Huc, I. and Candau, S. J.: Chem. Commun. (1997) 2105. Search in Google Scholar

8. Duivenvoorde, F. L., Feiters, M. C., van der Gaast, S. J. and Engberts, J. B. F. N.: Langmuir13 (1997) 3737. Search in Google Scholar

9. Zana, R.: J. Colloid. Interface Sci.248 (2002) 203. Search in Google Scholar

10. Zana, R. and Xia, J. D.: Gemini Surfactants, Dekker, New York2004. Search in Google Scholar

11. Lu, T., Han, F., Mao, G. R., Lin, G. F., Huang, J. B., Huang, X., Wang, Y. L. and Fu, H. L.: Langmuir23 (2007) 2932. Search in Google Scholar

12. Huo, Q., Leon, R., Petroff, P. M. and Stucky, G. D.: Nature268 (1995) 1324. Search in Google Scholar

13. Oda, R., Huc, I. and Candau, S. J.: Angew. Chem., Int. Ed.37 (1998) 2689. Search in Google Scholar

14. Coi, T. S., Shimizu, G., Shirai, M. and Hamada, K.: Dyes Pigments45 (2000) 145. Search in Google Scholar

15. Han, S. H., Xu, J., Hou, W. G., Yu, X. M. and Wang, Y. S.: J. Phys. Chem.B108 (2004) 15043. Search in Google Scholar

16. Gaël, R., Anthony, J., Kirby, S. R., Gary, W. and Patrick, C.: J. Chem. Soc., Perkin Trans.2 (2002) 13021306. Search in Google Scholar

17. Brannon, D. K.: Cosmetic Microbiology: a practical handbook. CRC Press, Inc., Boca Raton, Fla. (1997). Search in Google Scholar

18. Cole, E. C., Addison, R. M., Rubino, J. R., Leese, K. E., Dulaney, P. D., Newell, M. S., Wilkins, J., Gaber, D. J., Wineinger, T. and Criger, D. A.: J. Applied Microbiol.95 (2003) 664. Search in Google Scholar

19. Lu, T., Lan, Y., Liu, C., Huang, J. and Wang, Y.: J. Colloid. Interface Sci.377 (2012) 222230. Search in Google Scholar

20. Kosdapoff, G. M.: J. Am. Chem. Soc.68 (1946) 1670. Search in Google Scholar

21. Negm, N. A.: Egypt. J. Chem.45 (3) (2002) 483499. Search in Google Scholar

22. Mohamed, M. Z., Ismail, D. A. and Mohamed, A. S.: J. Surf. Det.8 (2) (2005) 175180. Search in Google Scholar

23. Laurier, L. S.: Advances in Chem. Series99 (1992) 231. Search in Google Scholar

24. Sjoblom, J.: Surfactant Science Series61 (2005) 237. Search in Google Scholar

25. Hikota, T. and Meguro, K.: J. Am. Oil Chem. Soc.47(007A) (1970) 158. Search in Google Scholar

26. Morsy, S. M. I.: Egypt. J. Petrol.1 (4) (2005) 918. Search in Google Scholar

27. Takeshita, T., Shimohara, T. and Maeda, S.: J. Am. Oil Chem. Soc.59 (1982) 104107. Search in Google Scholar

28. Sherman, J. H. and Taylor, R. T.: US. Pat. 6(007) (1999) 701. Search in Google Scholar

29. Al-Sabagh, A. M.: J. Poly. Adv. Technol.11 (2000) 465. Search in Google Scholar

30. Shuichi, M., Kazayasu, I., Sadao, Y., Kazuo, K. and Tsuyoshi, Y.: J. Am. Oil Chem. Soc.67 (1990) 996100. Search in Google Scholar

31. Rosen, M. J.: Surfactants and interfacial phenomena. Wiley, New York (1987) p 72. Search in Google Scholar

32. Rosen, M. J.: Surfactants and interfacial phenomena, 2nd edn.Wiley, New York (1989). Search in Google Scholar

33. Rosen, M. J. and Liu, L.: J. Am. Oil Chem. Soc.73 (1996) 885890. Search in Google Scholar

34. Hafiz, A. A., Negm, N. A. and Elawady, M. Y.: Egypt. J. Chem.47 (2004) 369383. Search in Google Scholar

35. Clape, S. P. and Infante, M. R.: Biocatal. Biotransfor.20 (4) (2002) 215233. Search in Google Scholar

36. El-Sukkary, M. M. A., Shaker, N. O., Ismail, D. A., Ahmed, S. M., Zaki, M. F. and Awad, A. I.: Egypt. J. Petrol. Vol. 21 (1) (2012) 3743. Search in Google Scholar

37. Badawi, A. M., Mohamed, D. E., Hafiz, A. A., Ahmed, S. M., Gohar, Y. M., üSoliman, E. A. and Said, M. S.: Mans. J. of Chem.37 (2) (2010) 230243. Search in Google Scholar

38. Negm, N. A., Zaki, M. F. and Salem, M. A. I.: Colloids Surf. B Biointerfaces77 (2010) 96. Search in Google Scholar

Received: 2013-2-26
Revised: 2013-3-21
Published Online: 2013-09-09
Published in Print: 2013-07-15

© 2013, Carl Hanser Publisher, Munich