Advertisement

Research on Chemical Intermediates

, Volume 42, Issue 3, pp 1913–1928 | Cite as

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

  • Monohar Hossain Mondal
  • Ankit Roy
  • Susanta Malik
  • Aniruddha Ghosh
  • Bidyut Saha
Review Paper

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.

Keywords

Cationic gemini Dimeric surfactants Green chemistry Catalysis 

References

  1. 1.
    F.M. Menger, C.A. Littau, J. Am. Chem. Soc. 115, 10083–10090 (1993)CrossRefGoogle Scholar
  2. 2.
    D. Chowdhury, P.K. Maiti, S. Sabhapandit, P. Taneja, Phys. Rev. E 56, 667–679 (1997)CrossRefGoogle Scholar
  3. 3.
    M. Rosen, ChemTech 23, 30–33 (1993)Google Scholar
  4. 4.
    R. Zana, M. Benrraou, R. Rueff, Langmuir 7, 1072–1075 (1991)CrossRefGoogle Scholar
  5. 5.
    D. Chowdhury, Langmuir 12, 1098–1103 (1996)CrossRefGoogle Scholar
  6. 6.
    F.M. Menger, J.S. Keiper, V. Azov, Langmuir 16, 2062–2067 (2000)CrossRefGoogle Scholar
  7. 7.
    M.J. Rosen, D.J. Tracy, J. Surfactants Deterg. 1, 547–554 (1998)CrossRefGoogle Scholar
  8. 8.
    Y.X. Ding, M. Zha, J. Zhang, S.S. Wang, Colloids Surf. A 298, 201–205 (2007)CrossRefGoogle Scholar
  9. 9.
    X. Huang, Y.C. Han, Y.X. Wang, Y. Wang, J. Phys. Chem. B 111, 12439–12446 (2007)CrossRefGoogle Scholar
  10. 10.
    D. Danino, Y. Talmon, R. Zana, Langmuir 14, 5412 (1998)CrossRefGoogle Scholar
  11. 11.
    L. Han, H. Chen, P. Luo, Viscosity behavior of cationic gemini surfactants with long alkyl chains. Surf. Sci. Ser. 564, 141–148 (2004)CrossRefGoogle Scholar
  12. 12.
    H. Chen, L. Han, P. Xu, Acta Phys. Chim. Sin. 19, 1020–1024 (2003)Google Scholar
  13. 13.
    Z. Ye, F. Zhang, L. Han, Colloids Surf. A 322, 138–141 (2008)CrossRefGoogle Scholar
  14. 14.
    W.H. Jia, X.P. Rao, Z.Q. Song, S.B. Shang, J. Surfactants Deterg. 12, 261–267 (2009)CrossRefGoogle Scholar
  15. 15.
    L.Y. Chen, G.Z. Fang, K. Liu, X. Hu, Chem. Ind. For. Prod. 27, 66–85 (2007)Google Scholar
  16. 16.
    X. Hu, H.C. Li, L.Y. Chen, Chin. J. Appl. Chem. 24, 1439–1442 (2007)Google Scholar
  17. 17.
    X.H. Wei, D.R. Cao, S.F. Dong, Guangzhou Chem. 3(1), 22–27 (2003)Google Scholar
  18. 18.
    C. Villa, S. Baldassari, D.F.C. Martino, A. Spinella, E. Caponetti, Materials 6, 150–157 (2013)Google Scholar
  19. 19.
    L.J. Chen, C.D. Chiu, F.S. Shau, J. Phys. Chem. B 106, 12782–12786 (2002)CrossRefGoogle Scholar
  20. 20.
    M. Gradzielski, Langmuir 14, 6037–6044 (1998)CrossRefGoogle Scholar
  21. 21.
    R. Aveyard, B.P. Binks, J. Chen, Langmuir 14, 4699–4709 (1998)CrossRefGoogle Scholar
  22. 22.
    K. Kalyanasundaram, J.K. Thomas, J. Am. Chem. Soc. 99, 2039 (1977)CrossRefGoogle Scholar
  23. 23.
    L. Han, Z. Ye, H. Chen, P. Luo, J. Surfactants Deterg. 12, 185–190 (2009)CrossRefGoogle Scholar
  24. 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)CrossRefGoogle Scholar
  25. 25.
    C.A. Bunton, L.B. Robinson, J. Schaak, M.F. Stam, J. Org. Chem. 36, 2346 (1971)CrossRefGoogle Scholar
  26. 26.
    S. Matsumura, Macromol. Biosci. 2(3), 105–126 (2002)CrossRefGoogle Scholar
  27. 27.
    N.V. Tsarevsky, K. Matyjaszewski, Chem. Rev. 107(6), 2270–2299 (2007)CrossRefGoogle Scholar
  28. 28.
    S. Kobayashi, A. Makino, Chem. Rev. 109(11), 5288–5353 (2009)CrossRefGoogle Scholar
  29. 29.
    R. Akiyama, S. Kobayashi, Chem. Rev. 109(2), 594–642 (2009)CrossRefGoogle Scholar
  30. 30.
    C.J. Li, L. Chen, Chem. Soc. Rev. 35(1), 68–82 (2006)CrossRefGoogle Scholar
  31. 31.
    J.J. Bozell, G.R. Petersen, Green Chem. 12(4), 539–554 (2010)CrossRefGoogle Scholar
  32. 32.
    P. Foley, A. Kermanshahi, E.S. Beach, J.B. Zimmerman, Chem. Soc. Rev. 41(4), 1499–1518 (2012)CrossRefGoogle Scholar
  33. 33.
    P.T. Anastas, J.C. Warner, Green chemistry: theory and practice (Oxford Science Publications, Oxford, 1998)Google Scholar
  34. 34.
    R. Zana, J. Colloid Interface Sci. 248, 203–220 (2002)CrossRefGoogle Scholar
  35. 35.
    R. Zana, Adv. Colloid Interface Sci. 97, 205–253 (2002)CrossRefGoogle Scholar
  36. 36.
    V.D. Sharma, M.A. Ilies, Med. Res. Rev. 34(1), 45–76 (2014)CrossRefGoogle Scholar
  37. 37.
    A. Rodriguez, M.M. Graciani, A.J. Moreno-Vargas, M.L. Moya, J. Phys. Chem. B 112, 11942–11949 (2008)CrossRefGoogle Scholar
  38. 38.
    J. Xia, R. Zana, Synthesis, Interfacial and Solution Phase Behaviour and Applications, Surfactant Science Series (Marcel Dekker, New York, 2004), pp. 301–319Google Scholar
  39. 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)Google Scholar
  40. 40.
    S.K. Hait, S.P. Moulik, J. Oleo Sci. 276, 231–238 (2004)Google Scholar
  41. 41.
    J. Feng, X. Liu, L. Zhang, S. Zhao, J. Yu, Langmuir 26, 11907–11914 (2010)CrossRefGoogle Scholar
  42. 42.
    B. Kumar, D. Tikariha, K.K. Ghosh, N. Barbero, P. Quagliotto, J. Phys. Org. Chem. 26(8), 626–631 (2013)CrossRefGoogle Scholar
  43. 43.
    W. Jiang, B. Xu, Q. Lin et al., J. Colloid Interface Sci. 311(2), 530–536 (2007)CrossRefGoogle Scholar
  44. 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. 129–192Google Scholar
  45. 45.
    I. Maliszewska, K.A. Wilk, B. Burczyk, L. Syper, Prog. Colloid Polym. Sci. 118, 172–177 (2001)CrossRefGoogle Scholar
  46. 46.
    K.A. Wilk, L. Syper, B. Burczyk, I. Maliszewska, M. Jon, B.W. Domagalska, J. Surfactants Deterg. 4, 155–163 (2001)CrossRefGoogle Scholar
  47. 47.
    L. Syper, K.A. Wilk, A. SokoÁowski, B. Burczyk, Prog. Colloid Polym. Sci. 110, 199–211 (1998)CrossRefGoogle Scholar
  48. 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. 49.
    M. Johnsson, A. Wagenaar, J.B.F.N. Engberts, J. Am. Chem. Soc. 125, 757–760 (2003)Google Scholar
  50. 50.
    K.A. Wilk, L. Syper, B. Burczyk, A. SokoÁowski, B.W. Domagalska, J. Surfactants Deterg.3(185), 552–558 (2000) Google Scholar
  51. 51.
    J. Eastoe, P. Rogueda, B.J. Harrison, A.M. Howe, A.R. Pitt, Langmuir 10, 4429–4443 (1994)CrossRefGoogle Scholar
  52. 52.
    J. Eastoe, P. Rogueda, A.M. Howe, A.R. Pitt, R.K. Heenan, Langmuir 12, 2701–2705 (1996)CrossRefGoogle Scholar
  53. 53.
    C.B.A. Briggs, I.M. Newington, A.R. Pitt, J. Chem. Soc., Chem. Commun. 3, 379–382 (1995)CrossRefGoogle Scholar
  54. 54.
    U.R.M. Kjellin, P.M. Claesson, E.N. Vulfson, Langmuir 17, 1941–1949 (2001)CrossRefGoogle Scholar
  55. 55.
    U. Laska, K.A. Wilk, I. Maliszewsk, L. Syper, J. Surfactants Deterg. 9(2), 68–82 (2006)CrossRefGoogle Scholar
  56. 56.
    T. Banno, T. Toyota and S. Matsumura. doi: 10.5772/56163
  57. 57.
    A.R. Tehrani-Bagha, H. Oskarsson, C.G. Ginkel, K. Holmberg, J. Colloid Interface Sci. 312(2), 444–452 (2007)CrossRefGoogle Scholar
  58. 58.
    A.R. Tehrani-Bagha, K. Holmberg, 26(12), 9276–9282 (2010)Google Scholar
  59. 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)CrossRefGoogle Scholar
  60. 60.
    J. Haldar, P. Kondaiah, S. Bhattacharya, J. Med. Chem. 48(11), 3823–3831 (2005)CrossRefGoogle Scholar
  61. 61.
    M.M.L. Chan, J.B. Robinson, J. Med. Chem. 17(10), 1057–1060 (1974)CrossRefGoogle Scholar
  62. 62.
    J.D. Hull, F. Scheinmann, N.J. Turner, Tetrahedron Asymmetry 14(5), 567–576 (2003)CrossRefGoogle Scholar
  63. 63.
    R.J. Kazlauskas, A.N.E. Weissfloch, J. Mol. Cat. B 3(1), 65–72 (1997)CrossRefGoogle Scholar
  64. 64.
    C. Larpent, X. Chasseray, Tetrahedron 48(19), 3903–3914 (1992)CrossRefGoogle Scholar
  65. 65.
    R.A. Moss, W.L. Sunshine, J. Org. Chem. 39(8), 1083–1089 (1974)CrossRefGoogle Scholar
  66. 66.
    V. Cherezov, M. Caffrey, Faraday Discuss. 136, 195–208 (2007)CrossRefGoogle Scholar
  67. 67.
    T.C.G. Kibbey, K.F. Hayes, Environ. Sci. Technol. 3, 1171–1187 (1997)CrossRefGoogle Scholar
  68. 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)CrossRefGoogle Scholar
  69. 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)CrossRefGoogle Scholar
  70. 70.
    G. Ronsin, C. Perrin, P. Guedat, A. Kremer, P. Camilleri, A. Kirby, J. Chem. Commun. (21), 2234–2235 (2001)Google Scholar
  71. 71.
    H.S. Rosenzweig, V.A. Rakhmanova, R.C. MacDonald, Bioconjugate Chem. 21, 258–263 (2001)CrossRefGoogle Scholar
  72. 72.
    I. Badea, R. Verrall, M. Baca-Estrada, S. Tikoo, A. Rosenberg, P. Kumar, M. Foldvari, J. Gene Med. 7, 1200–1214 (2005)CrossRefGoogle Scholar
  73. 73.
    L. Jing, W. Qiao. doi: 10.1039/c5sm00041f
  74. 74.
    W. Wang, Y. Han, M. Gao, Y. Wang, J. Nanopart. Res. 15, 1380–1383 (2013)CrossRefGoogle Scholar
  75. 75.
    T. Lu, F. Han, G. Mao, G. Lin, J. Huang, X. Huang, Y. Wang, H. Fu, Langmuir 23, 2932–2936 (2007)CrossRefGoogle Scholar
  76. 76.
    M. El. Achouri, M. R. Infante, F. Izquierdo, S. Kertit, H.M. Gouttaya, B. Nciri, Corros. Sci.43(1), 19–35(2001)Google Scholar

Copyright information

© Springer Science+Business Media Dordrecht 2015

Authors and Affiliations

  • Monohar Hossain Mondal
    • 1
  • Ankit Roy
    • 1
  • Susanta Malik
    • 1
  • Aniruddha Ghosh
    • 1
  • Bidyut Saha
    • 1
  1. 1.Homogeneous Catalysis Laboratory, Department of ChemistryThe University of BurdwanBurdwanIndia

Personalised recommendations