Skip to main content
SpringerLink
Log in

Review on chemically bonded geminis with cationic heads: second-generation interfactants

  • Review Paper
  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

Cationic gemini surfactants are a special class of second-generation smart surfactants. Since Menger first named them, gemini surfactants have drawn a wide and immense attraction from scientists throughout the whole world. These dimeric surfactants possess two or more hydrophilic with two or more hydrophobic head groups, chemically bonded with a linker, called the spacer group. These kinds of surfactants are used mainly in homogeneous catalytic reactions, as well as for solubilisation, emulsification, and many more technical applications. They are used in industries for electro-decoating, stabilization of adhesive polymer latex, anti-friction agents, mining, paper manufacturing, preparation of surfactants including softeners, cosmetics, and most importantly, recent advancement in drug designing, synthesis, and application in medicine. The aim of this paper is to bring attention to the high performance second generation interfactants, with a focus on their synthesis, structure, types, and greener industrial application with high possibility of future prospect.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Scheme 1
Scheme 2
Scheme 3
Scheme 4
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. F.M. Menger, C.A. Littau, J. Am. Chem. Soc. 115, 10083–10090 (1993)

    Article  CAS  Google Scholar 

  2. D. Chowdhury, P.K. Maiti, S. Sabhapandit, P. Taneja, Phys. Rev. E 56, 667–679 (1997)

    Article  CAS  Google Scholar 

  3. M. Rosen, ChemTech 23, 30–33 (1993)

    CAS  Google Scholar 

  4. R. Zana, M. Benrraou, R. Rueff, Langmuir 7, 1072–1075 (1991)

    Article  CAS  Google Scholar 

  5. D. Chowdhury, Langmuir 12, 1098–1103 (1996)

    Article  CAS  Google Scholar 

  6. F.M. Menger, J.S. Keiper, V. Azov, Langmuir 16, 2062–2067 (2000)

    Article  CAS  Google Scholar 

  7. M.J. Rosen, D.J. Tracy, J. Surfactants Deterg. 1, 547–554 (1998)

    Article  CAS  Google Scholar 

  8. Y.X. Ding, M. Zha, J. Zhang, S.S. Wang, Colloids Surf. A 298, 201–205 (2007)

    Article  CAS  Google Scholar 

  9. X. Huang, Y.C. Han, Y.X. Wang, Y. Wang, J. Phys. Chem. B 111, 12439–12446 (2007)

    Article  CAS  Google Scholar 

  10. D. Danino, Y. Talmon, R. Zana, Langmuir 14, 5412 (1998)

    Article  Google Scholar 

  11. L. Han, H. Chen, P. Luo, Viscosity behavior of cationic gemini surfactants with long alkyl chains. Surf. Sci. Ser. 564, 141–148 (2004)

    Article  CAS  Google Scholar 

  12. H. Chen, L. Han, P. Xu, Acta Phys. Chim. Sin. 19, 1020–1024 (2003)

    CAS  Google Scholar 

  13. Z. Ye, F. Zhang, L. Han, Colloids Surf. A 322, 138–141 (2008)

    Article  CAS  Google Scholar 

  14. W.H. Jia, X.P. Rao, Z.Q. Song, S.B. Shang, J. Surfactants Deterg. 12, 261–267 (2009)

    Article  CAS  Google Scholar 

  15. L.Y. Chen, G.Z. Fang, K. Liu, X. Hu, Chem. Ind. For. Prod. 27, 66–85 (2007)

    Google Scholar 

  16. X. Hu, H.C. Li, L.Y. Chen, Chin. J. Appl. Chem. 24, 1439–1442 (2007)

    CAS  Google Scholar 

  17. X.H. Wei, D.R. Cao, S.F. Dong, Guangzhou Chem. 3(1), 22–27 (2003)

    Google Scholar 

  18. C. Villa, S. Baldassari, D.F.C. Martino, A. Spinella, E. Caponetti, Materials 6, 150–157 (2013)

    Google Scholar 

  19. L.J. Chen, C.D. Chiu, F.S. Shau, J. Phys. Chem. B 106, 12782–12786 (2002)

    Article  CAS  Google Scholar 

  20. M. Gradzielski, Langmuir 14, 6037–6044 (1998)

    Article  CAS  Google Scholar 

  21. R. Aveyard, B.P. Binks, J. Chen, Langmuir 14, 4699–4709 (1998)

    Article  CAS  Google Scholar 

  22. K. Kalyanasundaram, J.K. Thomas, J. Am. Chem. Soc. 99, 2039 (1977)

    Article  CAS  Google Scholar 

  23. L. Han, Z. Ye, H. Chen, P. Luo, J. Surfactants Deterg. 12, 185–190 (2009)

    Article  CAS  Google Scholar 

  24. M. Damen, J. Aarbiou, S.F.M. van Dongen, R.M. Buijs-Offerman, P.P. Spijkers, M. van den Heuvel, K. Kvashnina, R.J.M. Nolte, B.J. Scholte, M.C. Feiters, J. Control. Release 145, 33–39 (2010)

    Article  CAS  Google Scholar 

  25. C.A. Bunton, L.B. Robinson, J. Schaak, M.F. Stam, J. Org. Chem. 36, 2346 (1971)

    Article  CAS  Google Scholar 

  26. S. Matsumura, Macromol. Biosci. 2(3), 105–126 (2002)

    Article  CAS  Google Scholar 

  27. N.V. Tsarevsky, K. Matyjaszewski, Chem. Rev. 107(6), 2270–2299 (2007)

    Article  CAS  Google Scholar 

  28. S. Kobayashi, A. Makino, Chem. Rev. 109(11), 5288–5353 (2009)

    Article  CAS  Google Scholar 

  29. R. Akiyama, S. Kobayashi, Chem. Rev. 109(2), 594–642 (2009)

    Article  CAS  Google Scholar 

  30. C.J. Li, L. Chen, Chem. Soc. Rev. 35(1), 68–82 (2006)

    Article  Google Scholar 

  31. J.J. Bozell, G.R. Petersen, Green Chem. 12(4), 539–554 (2010)

    Article  CAS  Google Scholar 

  32. P. Foley, A. Kermanshahi, E.S. Beach, J.B. Zimmerman, Chem. Soc. Rev. 41(4), 1499–1518 (2012)

    Article  CAS  Google Scholar 

  33. P.T. Anastas, J.C. Warner, Green chemistry: theory and practice (Oxford Science Publications, Oxford, 1998)

    Google Scholar 

  34. R. Zana, J. Colloid Interface Sci. 248, 203–220 (2002)

    Article  CAS  Google Scholar 

  35. R. Zana, Adv. Colloid Interface Sci. 97, 205–253 (2002)

    Article  CAS  Google Scholar 

  36. V.D. Sharma, M.A. Ilies, Med. Res. Rev. 34(1), 45–76 (2014)

    Article  Google Scholar 

  37. A. Rodriguez, M.M. Graciani, A.J. Moreno-Vargas, M.L. Moya, J. Phys. Chem. B 112, 11942–11949 (2008)

    Article  CAS  Google Scholar 

  38. J. Xia, R. Zana, Synthesis, Interfacial and Solution Phase Behaviour and Applications, Surfactant Science Series (Marcel Dekker, New York, 2004), pp. 301–319

    Google Scholar 

  39. M. Mishra, P. Muthuprasanna, P.S. Rani, I.A.S. Babu, I.S. Chandiran, G. Arunachalam, S. Shalini, Int. J. PharmTech Res. 1, 1354–1356 (2009)

    CAS  Google Scholar 

  40. S.K. Hait, S.P. Moulik, J. Oleo Sci. 276, 231–238 (2004)

    Google Scholar 

  41. J. Feng, X. Liu, L. Zhang, S. Zhao, J. Yu, Langmuir 26, 11907–11914 (2010)

    Article  CAS  Google Scholar 

  42. B. Kumar, D. Tikariha, K.K. Ghosh, N. Barbero, P. Quagliotto, J. Phys. Org. Chem. 26(8), 626–631 (2013)

    Article  CAS  Google Scholar 

  43. W. Jiang, B. Xu, Q. Lin et al., J. Colloid Interface Sci. 311(2), 530–536 (2007)

    Article  CAS  Google Scholar 

  44. B. Burczyk, Novel saccharide-based surfactants, in Novel Surfactants. Preparation, Applications, and Biodegradability, 2nd edn., ed. by K. Holmberg (Marcel Dekker, New York, 2003), pp. 129–192

    Google Scholar 

  45. I. Maliszewska, K.A. Wilk, B. Burczyk, L. Syper, Prog. Colloid Polym. Sci. 118, 172–177 (2001)

    Article  CAS  Google Scholar 

  46. K.A. Wilk, L. Syper, B. Burczyk, I. Maliszewska, M. Jon, B.W. Domagalska, J. Surfactants Deterg. 4, 155–163 (2001)

    Article  CAS  Google Scholar 

  47. L. Syper, K.A. Wilk, A. SokoÁowski, B. Burczyk, Prog. Colloid Polym. Sci. 110, 199–211 (1998)

    Article  CAS  Google Scholar 

  48. B. Burczyk, L. Syper, K.A. Wilk, New surface active aldonamides and their preparation. Pol. Pat. Appl. 33, 1294–1298 (1999)

    Google Scholar 

  49. M. Johnsson, A. Wagenaar, J.B.F.N. Engberts, J. Am. Chem. Soc. 125, 757–760 (2003)

  50. K.A. Wilk, L. Syper, B. Burczyk, A. SokoÁowski, B.W. Domagalska, J. Surfactants Deterg.3(185), 552–558 (2000)

  51. J. Eastoe, P. Rogueda, B.J. Harrison, A.M. Howe, A.R. Pitt, Langmuir 10, 4429–4443 (1994)

    Article  CAS  Google Scholar 

  52. J. Eastoe, P. Rogueda, A.M. Howe, A.R. Pitt, R.K. Heenan, Langmuir 12, 2701–2705 (1996)

    Article  CAS  Google Scholar 

  53. C.B.A. Briggs, I.M. Newington, A.R. Pitt, J. Chem. Soc., Chem. Commun. 3, 379–382 (1995)

    Article  Google Scholar 

  54. U.R.M. Kjellin, P.M. Claesson, E.N. Vulfson, Langmuir 17, 1941–1949 (2001)

    Article  CAS  Google Scholar 

  55. U. Laska, K.A. Wilk, I. Maliszewsk, L. Syper, J. Surfactants Deterg. 9(2), 68–82 (2006)

    Article  Google Scholar 

  56. T. Banno, T. Toyota and S. Matsumura. doi:10.5772/56163

  57. A.R. Tehrani-Bagha, H. Oskarsson, C.G. Ginkel, K. Holmberg, J. Colloid Interface Sci. 312(2), 444–452 (2007)

    Article  CAS  Google Scholar 

  58. A.R. Tehrani-Bagha, K. Holmberg, 26(12), 9276–9282 (2010)

  59. H.M. Willemen, L.C.P.M. de Smet, A. Koudijs, M.C.A. Stuart, I.G.A.M. Heikamp-de Jong, A.T.M. Marcelis, E.J.R. Sudhölter, Angew. Chem. Int. Ed. Engl. 41(22), 4275–4277 (2002)

    Article  CAS  Google Scholar 

  60. J. Haldar, P. Kondaiah, S. Bhattacharya, J. Med. Chem. 48(11), 3823–3831 (2005)

    Article  CAS  Google Scholar 

  61. M.M.L. Chan, J.B. Robinson, J. Med. Chem. 17(10), 1057–1060 (1974)

    Article  CAS  Google Scholar 

  62. J.D. Hull, F. Scheinmann, N.J. Turner, Tetrahedron Asymmetry 14(5), 567–576 (2003)

    Article  CAS  Google Scholar 

  63. R.J. Kazlauskas, A.N.E. Weissfloch, J. Mol. Cat. B 3(1), 65–72 (1997)

    Article  CAS  Google Scholar 

  64. C. Larpent, X. Chasseray, Tetrahedron 48(19), 3903–3914 (1992)

    Article  CAS  Google Scholar 

  65. R.A. Moss, W.L. Sunshine, J. Org. Chem. 39(8), 1083–1089 (1974)

    Article  CAS  Google Scholar 

  66. V. Cherezov, M. Caffrey, Faraday Discuss. 136, 195–208 (2007)

    Article  CAS  Google Scholar 

  67. T.C.G. Kibbey, K.F. Hayes, Environ. Sci. Technol. 3, 1171–1187 (1997)

    Article  Google Scholar 

  68. A.J. Kirby, 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.G. Rodriguez, P. Gudat, A. Kremer, C. McGregor, C. Perrin, G. Ronsin, M.C.P. van Eijk, Angew. Chem. Int. Ed. 42, 1448–1457 (2003)

    Article  CAS  Google Scholar 

  69. M.L. Fielden, C. Perrin, A. Kremer, M. Bergsma, M.C. Stuart, P. Camilleri, J.B.F.N. Engberts, Eur. J. Biochem. 268, 1269–1279 (2001)

    Article  CAS  Google Scholar 

  70. G. Ronsin, C. Perrin, P. Guedat, A. Kremer, P. Camilleri, A. Kirby, J. Chem. Commun. (21), 2234–2235 (2001)

  71. H.S. Rosenzweig, V.A. Rakhmanova, R.C. MacDonald, Bioconjugate Chem. 21, 258–263 (2001)

    Article  CAS  Google Scholar 

  72. I. Badea, R. Verrall, M. Baca-Estrada, S. Tikoo, A. Rosenberg, P. Kumar, M. Foldvari, J. Gene Med. 7, 1200–1214 (2005)

    Article  CAS  Google Scholar 

  73. L. Jing, W. Qiao. doi:10.1039/c5sm00041f

  74. W. Wang, Y. Han, M. Gao, Y. Wang, J. Nanopart. Res. 15, 1380–1383 (2013)

    Article  Google Scholar 

  75. T. Lu, F. Han, G. Mao, G. Lin, J. Huang, X. Huang, Y. Wang, H. Fu, Langmuir 23, 2932–2936 (2007)

    Article  CAS  Google Scholar 

  76. M. El. Achouri, M. R. Infante, F. Izquierdo, S. Kertit, H.M. Gouttaya, B. Nciri, Corros. Sci.43(1), 19–35(2001)

Download references

Author information

Authors and Affiliations

  1. Homogeneous Catalysis Laboratory, Department of Chemistry, The University of Burdwan, Burdwan, 713104, WB, India

    Monohar Hossain Mondal, Ankit Roy, Susanta Malik, Aniruddha Ghosh & Bidyut Saha

Authors
  1. Monohar Hossain Mondal
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ankit Roy
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Susanta Malik
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Aniruddha Ghosh
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Bidyut Saha
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Bidyut Saha.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Mondal, M.H., Roy, A., Malik, S. et al. Review on chemically bonded geminis with cationic heads: second-generation interfactants. Res Chem Intermed 42, 1913–1928 (2016). https://doi.org/10.1007/s11164-015-2125-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-015-2125-z

Keywords

Search

Navigation