Generic placeholder image

Letters in Organic Chemistry

Author(s): Nirmal Singh* and Lalit Sharma

DOI: 10.2174/1570178616666190123124727

DownloadDownload PDF Flyer Cite As
Synthesis of Carbohydrate Derived Non-ionic Gemini Surfactants and Study of Their Micellar and Reverse Micellar Behavior - A Review

Page: [607 - 614] Pages: 8

  • * (Excluding Mailing and Handling)

Abstract

Gemini surfactants (gemini) are a distinct class of amphiphiles having more than one hydrophobic tail and hydrophilic head group connected via a spacer. These surfactants usually have better surface active properties than corresponding conventional surfactant of equal chain length. Depending upon the nature of charge on head group, these geminis may be cationic or anionic. If there is no charge on head group, the geminis are termed as non-ionic. Carbohydrate derived gemini surfactants carry sugar moiety linked with each of the conventional surfactants, which are further connected by spacer. The sugar moiety was found to enhance the aggregation tendencies. Moreover, due to the presence of sugar moiety, these surfactants are non-toxic and biodegradable. Due to chiral nature of sugar moiety, these surfactants can be used for chiral recognition of some chiral drugs in order to improve their aqueous solubility. Non-ionic surfactants are more important than ionic surfactants as in the latter case, due to repulsion among the same charged head group, aggregation does not take place readily. However, in case of non-ionic surfactants, the head group carries no charge, so there is no repulsion, thus micelle forms easily and at low concentration. The only repulsive forces among head groups are due to hydration shell formed by solvent molecules.

Keywords: Non-ionic gemini surfactants, carbohydrate, micellization, reverse micellization, aggregation, carbohydrate.

Graphical Abstract

[1]
Bunton, C.A.; Robinson, L.B.; Schaak, J.; Stam, M.F. J. Org. Chem., 1971, 36(16), 2346-2350.
[2]
Zana, R.; Talmon, Y. Nature, 1993, 362, 228-230.
[3]
Menger, F.M.; Littau, C.A. J. Am. Chem. Soc., 1993, 115(22), 10083-10090.
[4]
Zana, R. Specialist surfactants.in: Robb, I.D. (ed.) Champman Hall Ltd. London, 1996.
[5]
Sharma, L.; Singh, S. Carbohydr. Res., 1995, 270, 43-49.
[6]
Sakai, K.; Tamura, M.; Umezawa, S.; Takamatsu, Y.; Torigue, K.; Yoshimura, T.; Esumi, K.; Sakai, H.; Abe, M. Colloids Surf. A., 2008, 328, 100-106.
[7]
Sakai, K.; Umezawa, S.; Tamura, M.; Takamatsu, Y.; Tsuchiya, K.; Torigoe, K.; Ohkubo, T.; Yoshimura, T.; Esumi, K.; Sakai, H.; Abe, M.J. Colloid Interf. Sci, 2008, 318, 440-448.
[8]
Wilk, K.A.; Laska, U.; Zielinski, K.; Olszowski, A. J. Photochem. Photobiol. Chem., 2011, 219, 204-210.
[9]
Deng, W.; Zhang, Y.; Zhong, Y.; Peng, J. J. Surfact Deterg., 2014, 17, 453-458.
[10]
Elworthy, P.H.; Florence, A.T.; MacFarlane, C.B. Solubilization by Surface-Active Agents; Chapman and Hall: London, 1968.
[11]
Sant, V.P.; Smith, D.; Leroux, J-C. J. Contr. Rel, 2005, 104, 289-300.
[12]
Bromberg, L. J. Contr. Rel, 2008, 128, 99-112.
[13]
Gaucher, G.; Satturwar, P.; Jones, M-C.; Furtos, A.; Lerous, J-C. J. Phama. Bipharm., 2010, 76, 147-158.
[14]
Dembitsky, V. Lipids, 2004, 39, 933-953.
[15]
Queneau, Y.; Chambert, S.; Besset, C.; Cheaib, R. Carbo. Res., 2008, 343, 1999-2009.
[16]
Ruiz, C. Sugar-Based Surfactants Fundamentals and Applications; CRC Press, 2009.
[17]
Razafindralambo, H.; Blecker, C.; Paquot, M. Screening of Basic Properties of Amphiphilic Molecular Structures for Colloidal System Formation and Stability: The Case of Carbohydrate-Based Surfactants. In: Amphiphiles: Molecular Assembly and Applications; ACS: Washington, 2011.
[18]
Hill, K.; LeHen-Ferrenbach, C. Sugar-based surfactants fundamentals and Applications; CRC Press, 2009.
[19]
Kitamoto, D.; Morita, T.; Fukuoka, T.; Konishi, M.; Imura, T. Curr. Opin. Colloid Interf Sci., 2009, 14, 315-328.
[20]
Razafindralambo, H.; Blecker, C.; Paquot, M. Amphiphiles: Molecular Assembly and Applications; ACS: Washington, 2011.
[21]
Eastoe, J.; Rogueda, P.; Harrison, B.J.; Howe, A.M.; Pitt, A.R. Langmuir, 1994, 10, 4429-4433.
[22]
Eastoe, J.; Rogueda, P.; Howe, A.M.; Pitt, A.R.; Heenan, R.K. Langmuir, 1996, 12, 2701-2705.
[23]
Sharma, L. J. Incl. Phenom. Mol. Recogn. Chem., 1998, 31, 161-167.
[24]
Castro, M.J.L.; Kovensky, J.; Cirelli, A.F. Tetrahedron Lett., 1997, 38, 3995-3998.
[25]
Castro, M.J.L.; Kovensky, J.; Cirelli, A.F. Tetrahedron, 1999, 55, 12711-12722.
[26]
Singh, N.; Sharma, L. Tenside Surfact. Det, 2018, 55, 220-225.
[27]
Sharma, L.; Singh, S. Carbo. Res, 1995, 270, 43-49.
[28]
Pestman, J.M.; Terpstra, R.; Stuart, M.C.A.; van Doren, H.A.; Brisson, A.; Kellogg, R.M.; Engberts, J.B.F.N. Langmuir, 1997, 25, 6857-6860.
[29]
Castro, M.J.L.; Kovensky, J.; Cirelli, A.F. Tetrahedron, 1999, 55, 12711-12722.
[30]
Rose, J.D.; Maddry, J.A.; Comber, R.N.; Suling, W.J.; Wilson, L.N.; Reynolds, R.C. Carbohydr. Res., 2002, 337, 105-120.
[31]
Wilk, K.A.; Syper, L.; Domagalska, B.W.; Komorek, U.; Maliszewska, I.; Gancarz, R. J. Surfact. Det, 2002, 5, 235-244.
[32]
Castro, M.J.L.; Kovensky, J.; Cirelli, A.F. Molecules, 2000, 5, 608-609.
[33]
Castro, M.J.L.; Kovenskyl, J.; Cirelli, A.F. Langmuir, 2002, 18, 2477-2482.
[34]
Castro, M.J.L.; Kovensky, J.; Cirelli, A.F. Arkivoc, 2005, 12, 252-267.
[35]
Castro, M.J.L.; Cirelli, A.F.; Kovensky, J. J. Surf. Deterg, 2006, 9, 279-286.
[36]
Han, F.; Zhang, G. J. Surf. Deterg, 2004, 7, 175-180.
[37]
Warwel, S.; Briise, F. J. Surf. Deterg., 2004, 7, 187-193.
[38]
Warwel, S.; Briise, F.; Schier, H. J. Surf. Deterg., 2004, 7, 181-186. b
[39]
Yoshimura, T.; Ishihara, K.; Esumi, K. Langmuir, 2005, 21, 10409-10415.
[40]
Sakai, K.; Umezawa, S.; Tamura, M.; Takamatsu, Y.; Tsuchiya, K.; Torigoe, K.; Ohkubo, T.; Yoshimura, T.; Esumi, K.; Sakai, H.; Abe, M. J. Colloid Interf Sci., 2008, 318, 440-448.
[41]
Lakhrissi, L.; Hassan, N.; Lakhrissi, B.; Massoui, M.; Essassi, E.M.; Ruso, J.M.; Solans, C.; Rodriguez-Abreu, C. J. Surfact Deterg., 2011, 14, 487-495.
[42]
Yoshimura, T.; Umezawa, S.; Fujino, A.; Toriogoe, K.; Esumi, K.; Sakai, K.; Sakai, H.; Abe, M. J. Oleo Sci., 2013, 62, 353-362.
[43]
Liu, S.; Sang, R.; Hong, S.; Cai, Y.; Wang, H. Langmuir, 2013, 29, 8511-8516.
[44]
Zeng, X.; Wang, H.; Chen, Y.; Wang, L. Tenside Surfact Deterg., 2014, 51, 427-431.
[45]
Sharma, L.; Singh, N. Tenside Surfactants Deterg., 2014, 51, 441-444.
[46]
Sharma, L.; Singh, N. J. Surfact Deterg., 2015, 18, 33-39.
[47]
Fielden, M.L.; Perrin, C.; Kermer, A.; Bergsma, M.; Stuart, M.C.; Engerts, J.B.F.N. Eur. J. Biochem., 2001, 268, 1269-1279.
[48]
Johnsson, M.; Engberts, J.B.F.N. J. Phys. Org. Chem., 2004, 17, 934-944.
[49]
Johnsson, M.; Wagenaar, A.; Stuart, M.C.; Engberts, J.B.F.N. Langmuir, 2003, 19, 4609-4618.
[50]
Klijn, J.E.; Marc, C.A.; Scarzello, M.; Wagenaar, A.; Engberts, J.B.F.N. J. Phys. Chem. B, 2007, 111, 5204-5211.
[51]
Klijn, J.E.; Stuart, M.C.A.; Scarzello, M.; Wagenaar, A.; Engberts, J.B.F.N. J. Phys. Chem. B, 2006, 110, 21694-21700.
[52]
Sakai, K.; Umezawa, S.; Tamura, M.; Takamatsu, Y.; Tsuchiya, K.; Torigoe, K.; Ohkubo, T.; Yoshimura, T.; Esumi, K.; Sakai, H.; Abe, M. J. Colloid Interf Sci., 2008, 318, 440-448.
[53]
Kielec, J.M.; Valentine, K.G.; Babu, C.R.; Wand, A.J. Structure, 2009, 17, 346-351.
[54]
Sharma, L.; Singh, S. Carb. Res, 1995, 270, 43-49.
[55]
Lakhrissi, L.; Hassan, N.; Lakhrissi, B.; Massoui, M.; Essassi, E.M.; Ruso, J.M.; Solans, C.; Rodriguez-Abreu, C.J. Surfact. Deterg, 2011, 14, 487-495.
[56]
Guyong, W.; Wenshan, Q.; Zhiping, D.; Wanxu, W.; Qiuxiao, L. J. Phys. Chem. B, 2013, 117, 3154-3160.
[57]
Van Doren, H.A.; Smits, E.; Pestman, J.M.; Engberts, J.B.F.N.; Kellogg, R.M. Chem. Soc. Rev., 2000, 29, 183-199.
[58]
Yoshimura, T.; Ishihara, K.; Esumi, K. Langmuir, 2005, 21, 10409-10415.
[59]
Sakai, K.; Umezawa, S.; Tamura, M.; Takamatsu, Y.; Tsuchiya, K.; Torigoe, K.; Ohkubo, T.; Yoshimura, T.; Esumi, K.; Sakai, H.; Abe, M. J. Colloid Interf Sci., 2008, 318, 440-448.
[60]
Castro, M.J.L.; Cirelli, A.F.; Kovensky, J. J. Surf. Deterg, 2006, 9, 279-286.
[61]
Matsubara, H.; Takumi, H.; Takamatsu, T.; Takiue, T.; Aratono, M. Colloid Polym. Sci., 2009, 287, 1077-1082.