Abstract
Gemini surfactants are most exciting new types of surfactants. They have two hydrophilic head groups and two hydrophobic groups in a molecule separated by a spacer group. Nowadays different types of geminis have been synthesized. Geminis show some characteristic features like low cmc, high surface activity, high solubility in water, good foaming and wetting properties, as well as low Krafft temperature. Geminis imply low eye and skin irritation. These surfactants are widely used as antifoaming and antimicrobial agents. This review paper deals with synthesis, properties and applications of various gemini surfactants.
Kurzfassung
Gemini-Tenside sind hochinteressante neue Tensidtypen. Sie besitzen, getrennt durch ein Spacer-Gruppe, zwei hydrophile Kopfgruppen und zwei hydrophobe Gruppen innerhalb eines Moleküls. Heutzutage werden verschiedene Typen an Gemini-Tensiden synthetisiert, die einige charakteristische Eigenschaften wie niedrige cmc, hohe Oberflächenaktivität, hohe Wasserlöslichkeit, gute Schaum- und Benetzungseigenschaften sowie eine niedrige Krafft-Temperatur aufweisen. Gemini-Tenside implizieren geringe Augen- und Hautirritationen und werden häufig als Entschäumer und antimikrobielles Hilfsmittel eingesetzt. Dieser Übersichtsartikel behandelt Synthese, Eigenschaften und Applikationen verschiedener Gemini-Tenside.
References
1. Moulik, S. P.: Curr. Sci.71 (1996) 368–376.Search in Google Scholar
2. Paul, B. K. and Moulik, S. P.: Ibid.80 (2001) 990–1001.Search in Google Scholar
3. Niedral, J. B. and Lanzilotti, A. E.: J. Am. Chem. Soc.66 (1944) 844–852.Search in Google Scholar
4. Bunton, C. A., Robinson, L., Sehaak, J. and Stern, M. F.: J. Org. Chem.36 (1971) 2346–2350.10.1021/jo00815a033Search in Google Scholar
5. Devinsky, F., Masarova, L. and Lacko, I.: J. Colloid Interface Sci.105 (1985) 235–239.10.1016/0021-9797(85)90363-7Search in Google Scholar
6. Zhu, Y. P., MasuyanaA. and Okahara, M.: J. Am. Oil Chem. Soc.67 (1990) 459–463.10.1007/BF02638962Search in Google Scholar
7. Menger, F. M. and Keiper, J. S.: Angew Chem Int. Ed. Engl.39 (2000) 1906–1920.10.1002/1521-3773(20000602)39:11<1906::AID-ANIE1906>3.0.CO;2-QSearch in Google Scholar
8. Hait, S. K. and Moulik, S. P.: Curr. Sci.82 (2002) 101–111.Search in Google Scholar
9. Renouf, P., Mioskowski, C., Leabeau, I., Hebrault, D. and Desmurs, J.-R.: Tetrahedron Lett.39 (1998) 1357–1360.10.1016/S0040-4039(97)10835-8Search in Google Scholar
10. Oda, R., Huc, J. and Canadeu, S. J.: J. Chem. Commun. (1997) 2105–2106.10.1039/a704069eSearch in Google Scholar
11. Shula, D. and Tyagi, V.: J. Oleo. Sci.55 (2006) 381–390.10.5650/jos.55.381Search in Google Scholar
12. Shula, D. and Tyagi, V.: J. Oleo. Sci.55 (2006) 215–226.10.5650/jos.55.215Search in Google Scholar
13. Zana, R. and Xia, J.: (2003) 331.Search in Google Scholar
14. Moulik, S. P. and Mukherjee, K.: Proc. Indian. Natl. Sci. acad. Part A62 (1996) 215–232.Search in Google Scholar
15. Barres, C. S., Dupuich, C. M. and Lattes, I. R.: New. J. Chem.19 (1995) 345–347.Search in Google Scholar
16. Zana, R., Benrroau, M. and Rueff, R.: Langmuir7 (1991) 1072–1075.10.1021/la00054a008Search in Google Scholar
17. De, S., Aswal, V. K., Goyal, P. S. and Bhattacharya, S.: J. Phy. Chem. B102 (1998) 6125–6160.10.1021/jp980836cSearch in Google Scholar
18. Kim, T. S., Kida, T., Nakatsuji, Y., Hirao, T. and Ikeda, I.: J. Am. Oil Chem. Soc.73 (1996) 907–911.10.1007/BF02517994Search in Google Scholar
19. Menger, F. M. and Littau, C. A.:. J. Am. Chem. Soc.113 (1991) 1451–1452.10.1021/ja00004a077Search in Google Scholar
20. Esumi, K., Goino, M. and Koide, Y.: J. Colloid Interface Sci.183 (1996) 539–545.10.1006/jcis.1996.0577Search in Google Scholar
21. Menger, F. M. and Littau, C. A.: J. Am. Chem. Soc.115 (1993) 10083–10090.10.1021/ja00075a025Search in Google Scholar
22. Duienvoorde, F. L., Feiters, M. C., Jvan, D., Gaast, S. and Engberts, J. B. F. N.: Langmuir13 (1997) 3737–3743.10.1021/la9620420Search in Google Scholar
23. Eastoe, J., Rogueda, P., Howe, A. M., Pitt, A. R. and Heenan, R. K.: Langmuir12 (1996) 2701–2705.10.1021/la950827kSearch in Google Scholar
24. Pestman, J. M., Terpstra, K. R., Stuart, M. C. A., VanDoren, H. A., Brission, A., Kellogg, R. M. and Engberts, J. B. F. N.: Langmuir13 (1997) 6857–6870.10.1021/la970681kSearch in Google Scholar
25. Menger, F. M., Keiper, J. S., Mbadugha, B. N. A.: J. Am. Chem. Soc.123 (2001) 875–885.10.1021/ja0033178Search in Google Scholar
26. Castro, M. J. L., Kovensky, J. and Fernandez, A. C.: Tetrahedron Lett.38 (1997) 3995–3998.10.1016/S0040-4039(97)00817-4Search in Google Scholar
27. Sommerdijk, N. J. M., Hoeks, T. H. L., Synak, M., Fieters, M. C., Nolte, R. J. M. and Zwanenburg, B.: J. Am. Chem. Soc.119 (1997) 4338–4344.10.1021/ja962303sSearch in Google Scholar
28. Baumann, T. F.: J. Am. Chem. Soc.118 (1996) 10479–10486.10.1021/ja9619115Search in Google Scholar
29. Sibert, J. W., Baumann, T. F., Williams, D. J., White, A. J. P., Barrett, A. G. M. and Hoffman, B. M.: Ibid.118 (1996) 10487–10493.Search in Google Scholar
30. Michel, S. L. J., Goldberg, D. P., Stern, C., Barrett, A. G. M. and Hoffman, B. M.: Ibid.123 (2001) 4741–4748.Search in Google Scholar
31. Sekhon, B. S.: Resonance (2004) 42–49.10.1007/BF02834987Search in Google Scholar
32. Reiss-Husson, F. and Luzzati, V.: J. Phys. Chem.68 (1964) 3504–3511.10.1021/j100794a011Search in Google Scholar
33. Aswal, V. K., De Goyal, P. S., Bhattacharya, S. and Heenan, R. K.: J. Chem. Soc, Faraday Trans.94 (1998) 2965–2967.10.1039/a805307cSearch in Google Scholar
34. Menger, F. M. and Littau, C. A.: J. Am. Chem. Soc.115 (1993) 10083–10090.10.1021/ja00075a025Search in Google Scholar
35. Rosen, M. J.: Surfactants and Interfacial Phenomena, Wiley, New York, 1989, 2nd edn. 84–90.Search in Google Scholar
36. Parez, L., Pinazo, A., Rosen, M. J. and Infante, M. R.: Langmuir14 (1998) 2307–2315.10.1021/la971135uSearch in Google Scholar
37. Song, L. D. and Rosen, M. J.: Langmuir12 (1996) 1149–1153.10.1021/la950508tSearch in Google Scholar
38. Rosen, M. J.: J. Am. Chem. Soc.73 (1996) 885–890.Search in Google Scholar
39. Moulik, S. P., Haque, Md. E., Janan, P. K. and Das, A. R.: J. Phys. Chem.100 (1996) 701–708.10.1021/jp9506494Search in Google Scholar
40. Yekta, A., Aikawa, M. and Turro, N. J.: Chem. Phys. Lett.63 (1979) 543–552.10.1016/0009-2614(79)80710-1Search in Google Scholar
41. Turro, N. J., Gratzel, M. and Braum, A. M.: Angew. Chem. Inted. Engl.19 (1980) 675–682.10.1002/anie.198006751Search in Google Scholar
42. Menger, F. M., Keiper, J. S., Mbadugha, B. N. A., Caran, K. L. and Romsted, L. S.: Langmuir16 (2000) 9095–9078.10.1021/la0003692Search in Google Scholar
43. Manne, S., Schaffer, T. E., Huo, Q., Hausma, P., Morse, D. E., Stucky, G. D. and Axayla, I. A.: Langmuir13 (1997) 6382–6387.10.1021/la970070sSearch in Google Scholar
44. De, S., Aswal, V. K., Goyal, P. S. and Battacharaya, S.: Chem. Phys. Lett.303 (1999) 295–303.10.1016/S0009-2614(99)00207-9Search in Google Scholar
45. McBain, J. W. and Richards, P. H.: Ind. Eng. Chem.38 (1946) 642–646.10.1021/ie50438a029Search in Google Scholar
46. Kelvens, H. B.: Chem. Rev.47 (1950).10.1021/cr60146a001Search in Google Scholar
47. Engbert, J. B. F. N., Dam, T., Karthauser, J., Karborni, S. and Van Oo, N. M.: J. Colloid. Surf. A118 (1996) 41–49.10.1016/0927-7757(95)03383-1Search in Google Scholar
48. Satio, S.: J. Phys. Chem.89 (1985) 2110–2113.10.1021/j100256a061Search in Google Scholar
49. Dam, T., Engberts, J. B. F. N., Karthauser, J. S., Naraborni, N. M. and Vano, S.: J. Colloid. Surf. A118 (1996) 41–49.10.1016/0927-7757(95)03383-1Search in Google Scholar
50. Mecozzi, S., West, A. P. and Dougnerty, D.: J. Am. Chem. Soc.118 (1996) 2307–2308.10.1021/ja9539608Search in Google Scholar
51. Zhu, Y., Masuyama, A., Kirito, Y., Okahara, M. and Rosen, M. J.: J. Am. Oil Chem. Soc.69 (1992) 626–632.10.1007/BF02635800Search in Google Scholar
52. Rosen, M. J., Zhu, Z. H. and Hua, X. Y.: J. Am. Chem. Soc.69 (1992) 30–38.Search in Google Scholar
53. Rosen, M. J. and Zhu, Z. H.: J. Am. Chem. Soc.70 (1993) 65–72.Search in Google Scholar
54. Kwetkat, K. (HULSAG): Chem Abs.127 (1997) 249754.Search in Google Scholar
55. Diz, M., Manresa, A., Pinazo, A., Erra, P. and Infante, M. R.: J. Chem. Soc. Perkin Trans2 (1994) 1871–1879.10.1039/p29940001871Search in Google Scholar
56. Macian, M., Seguer, J., Infante, M. R., Selve, C. and Vindardell, M. P.: Toxicology106 (1996) 1–9.10.1016/0300-483X(95)03131-XSearch in Google Scholar
57. Castro, M. J. L., Kovensky, J. and Fernandez, A. C.: ARKIVOC.12 (2005) 253–267.Search in Google Scholar
58. Tehrani-Bagha, A. R., Oskarsson, H., van Ginkel, C. G. and Holmberg, K.: J. Colloid and Interface.312 (2007) 444–452.10.1016/j.jcis.2007.03.044Search in Google Scholar PubMed
59. TomokazuYoshimura, KanaIshihara and KunioEsumi: Langmuir21 (2005) 10409–10415.10.1021/la051614qSearch in Google Scholar PubMed
© 2009, Carl Hanser Publisher, Munich