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Solubilization of Hydrophobic Dyes in Surfactant Solutions

Tehrani-Bagha, Ali, Holmberg, Krister·2013·Materials
DOI 10.3390/ma6020580PMC PMC5452102
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Abstract

In this paper, the use of surfactants for solubilization of hydrophobic organic dyes (mainly solvent and disperse dyes) has been reviewed. The effect of parameters such as the chemical structures of the surfactant and the dye, addition of salt and of polyelectrolytes, pH, and temperature on dye solubilization has been discussed. Surfactant self-assemble into micelles in aqueous solution and below the concentration where this occurs—the critical micelle concentration (CMC)—there is no solubilization. Above the CMC, the amount of solubilized dye increases linearly with the increase in surfactant concentration. It is demonstrated that different surfactants work best for different dyes. In general, nonionic surfactants have higher solubilization power than anionic and cationic surfactants. It is likely that the reason for the good performance of nonionic surfactants is that they allow dyes to be accommodated not only in the inner, hydrocarbon part of the micelle but also in the headgroup shell. It is demonstrated that the location of a dye in a surfactant micelle can be assessed from the absorption spectrum of the dye-containing micellar solution.

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Research works printed but not linked: 95

  1. Mcbain, 1944, Solubilization and the colloidal micelles in soap solution, J. Am. Chem. Soc., 66, 9, 10.1021/ja01229a004 · DOI
  2. McBain, 1941, The solubilization of water-insoluble dye in dilute solutions of aqueous detergents, J. Am. Chem. Soc., 63, 670, 10.1021/ja01848a011 · DOI
  3. Merrill, 1942, Studies on solubilization, J. Phys. Chem., 46, 10, 10.1021/j150415a002 · DOI
  4. Green, 1947, Solubilization of water-insoluble dye by pure soaps and detergents of different types, J. Phys. Chem., 51, 286, 10.1021/j150451a022 · DOI
  5. Kolthoff, 1948, Solubilization of dimethylaminoazobenzene in solutions of detergents. I: The effect of temperature on the solubilization and upon the critical concentration, J. Phys. Colloid Chem., 52, 915, 10.1021/j150462a001 · DOI
  6. McBain, 1948, Solubilization of water-insoluble dye by colloidal electrolytes and non-ionizing detergents, J. Phys. Colloid Chem., 52, 12, 10.1021/j150457a002 · DOI
  7. Rosen, M.J. (2004). Surfactants and Interfacial Phenomena, Wiley. [3rd ed.]. · DOI
  8. Holmberg, K., Jonsson, B., Kronberg, B., and Lindman, B. (2003). Surfactant and Polymers in Aqueous Solution, John Wiley & Sons Ltd.. [2nd ed.]. · DOI
  9. Oakes, 2004, Physical interactions of dyes in solution—Influence of dye structure on aggregation and binding to surfactants/polymers, Rev. Prog. Coloration, 34, 110, 10.1111/j.1478-4408.2004.tb00156.x · DOI
  10. Oakes, 2003, Solubilisation of dyes by surfactant micelles. Part 2: Molecular interactions of azo dyes with cationic and zwitterionic surfactants, Color. Technol., 119, 100, 10.1111/j.1478-4408.2003.tb00157.x · DOI
  11. Oakes, 2003, Solubilisation of dyes by surfactant micelles. Part 1: Molecular interactions of azo dyes with nonionic and anionic surfactants, Color. Technol., 119, 91, 10.1111/j.1478-4408.2003.tb00156.x · DOI
  12. Oakes, 2003, Solubilisation of dyes by surfactant micelles. Part 3: A spectroscopic study of azo dyes in surfactant solutions, Color. Technol., 119, 301, 10.1111/j.1478-4408.2003.tb00188.x · DOI
  13. Tavares, 2005, Micellar solubilization of drugs, J. Pharm. Sci., 8, 147
  14. Kumar, 2010, Review of solubilization techniques for a poorly water-soluble drug: Carbamazepine, PDA J. Pharm. Sci. Technol., 64, 264
  15. Bhat, 2008, Solubilization capabilities of some cationic, anionic, and nonionic surfactants toward the poorly water-soluble antibiotic drug erythromycin, J. Chem. Eng. Data, 53, 1271, 10.1021/je700659g · DOI
  16. Liu, R. (2008). Water-Insoluble Drug Formulation, CRC Press. · DOI
  17. Torchilin, 2001, Structure and design of polymeric surfactant-based drug delivery systems, J. Control. Release, 73, 137, 10.1016/S0168-3659(01)00299-1 · DOI
  18. Banat, 1996, Microbial decolorization of textile-dye-containing effluents: A review, Bioresour. Technol., 58, 217, 10.1016/S0960-8524(96)00113-7 · DOI · Paper page
  19. Kant, 2012, Textile dyeing industry and environmental hazard, Nat. Sci., 4, 22
  20. Leube, H., Ruttiger, W., Kuhnel, G., Wolff, J., Ruppert, G.N., Schmit, M., Heid, C., Huckel, M., Flath, H.-J., Beckmann, W., Brossmann, R., Soll, M., and Sewekow, U. (2000). Ullmanns’ Encyclopedia of Industrial Chemistry, Wiley-VCH. [6th ed.].
  21. Holme, 2002, Recent developments in colorants for textile applications, Surf. Coat. Int. B, 85, 243, 10.1007/BF02699548 · DOI
  22. Rouette, H.K. (2001). Encyclopedia of Textile Finishing, Springer. · DOI
  23. Fourness, 1956, The disperse dyes—Their development and application, J. Soc. Dye. Colour., 72, 513, 10.1111/j.1478-4408.1956.tb02113.x · DOI
  24. Giles, 1971, The coloration of synthetic polymers: A review of the chemistry of dyeing of hydrophobic fibres, Br. Polym. J., 3, 279, 10.1002/pi.4980030607 · DOI
  25. Burkinshaw, S.M. (1995). Chemical Principles of Synthetic Fibre Dyeing, Blackie Academic & Professional, an Imprint of Chapman & Hall. · DOI
  26. Steingruber, E. (2000). Ullmann’s Encyclopedia of Industrial Chemistry, Wiley-VCH.
  27. Muthyala, R. (2002). Chemistry and Applications of Leuco Dyes, Kluwer Academic Publishers. · DOI
  28. Chao, 1998, Dyeing of cotton-polyester blends with anthraquinonoid vat dyes, Dye. Pigment., 40, 59, 10.1016/S0143-7208(98)00033-3 · DOI
  29. Nagl, G. (2000). Ullmann’s Encyclopedia of Industrial Chemistry, Wiley-VCH.
  30. Wood, 1976, Sulphur dyes 1966–1976, Rev. Prog. Coloration, 7, 80, 10.1111/j.1478-4408.1976.tb00236.x · DOI
  31. Guest, 1989, Sulphur dyes, Rev. Prog. Coloration, 19, 63, 10.1111/j.1478-4408.1989.tb03762.x · DOI
  32. Senior, J., Guest, R.A., and Wood, W.E. (2000). Kirk-Othmer Encyclopedia of Chemical Technology, John Wiley and Sons, Inc.
  33. Myers, D. (2006). Surfactant Science and Technology, John Wiley and Sons, Inc.. [3rd ed.].
  34. Edser, 2008, Status of global surfactant markets, Focus Surfactant, 2008, 1
  35. Reznik, 2010, Use of sustainable chemistry to produce an acyl amino acid surfactant, Appl. Microbiol. Biotechnol., 86, 1387, 10.1007/s00253-009-2431-8 · DOI
  36. Zemb, T., and Testard, F. (2002). Solubilization, John Wiley & Sons, Inc.
  37. Schott, 1967, Solubilization of a water-insoluble dye, J. Phys. Chem., 71, 3611, 10.1021/j100870a041 · DOI
  38. Choi, 2000, Solubilization of disperse dyes in cationic gemini surfactant micelles, Dye. Pigment., 45, 145, 10.1016/S0143-7208(00)00015-2 · DOI
  39. Singh, 2012, Solubilization of two organic dyes by cationic ester-containing gemini surfactants, J. Colloid Interf. Sci., 376, 112, 10.1016/j.jcis.2012.02.016 · DOI
  40. Singh, 2013, Solubilization of two organic water-insoluble dyes by anionic, cationic and nonionic surfactants, Colloid Surf. A, 417, 133, 10.1016/j.colsurfa.2012.10.006 · DOI
  41. Skoog, D.A., West, D.M., and Holler, F.J. (2000). Analytical Chemistry: An Introduction, Saunders College Pub.. [7th ed.].
  42. Tokiwa, 1968, Solubilization behavior of sodium dodecylpolyoxyethylene sulfates in relation to their polyoxyethylene chain lengths, J. Phys. Chem., 72, 1214, 10.1021/j100850a024 · DOI
  43. Schott, 1966, Solubilization of a water-insoluble dye as a method for determining micellar molecular weights, J. Phys. Chem., 70, 2966, 10.1021/j100881a041 · DOI
  44. Anacker, 1968, Comments on the paper “Solubilization of a water-insoluble dye as a method for determining micellar molecular weights” by hans schott, J. Phys. Chem., 72, 379, 10.1021/j100847a086 · DOI
  45. Herzog, 1994, Characterization of worm-like micelles containing solubilized dye-molecules by light scattering techniques, J. Colloid Interf. Sci., 164, 370, 10.1006/jcis.1994.1179 · DOI
  46. Birdi, 1976, Thermodynamics of mieellar solubilization of various water-insoluble dyes, Colloid Polym. Sci., 254, 1059, 10.1007/BF01602637 · DOI
  47. Hartley, 1938, The solvent properties of aqueous solutions of paraffin-chain salts. Part I. The solubility of trans-azobenzene in solutions of cetylpyridinium salts, J. Chem. Soc., 370, 1968, 10.1039/jr9380001968 · DOI
  48. Mata, 2005, Aggregation behavior of quaternary salt based cationic surfactants, Thermochim. Acta, 428, 147, 10.1016/j.tca.2004.11.009 · DOI
  49. Abe, 1987, Solubilization properties of aqueous solutions of alkyltrimethylammonium halides toward a water-insoluble dye, Colloid Polym. Sci., 265, 637, 10.1007/BF01412780 · DOI
  50. Fujio, 2004, Solubilization of a water-insoluble dye in aqueous NaBr solutions of alkylpyridinium bromides and its relation to micellar size and shape, Colloid Polym. Sci, 282, 223, 10.1007/s00396-003-0896-z · DOI
  51. Jacobs, 1972, A comparison of micellar aggregation numbers as determined by dye solubilization and light scattering, J. Colloid Interf. Sci., 89, 611, 10.1016/0021-9797(72)90069-0 · DOI
  52. McBain, 1946, Solubilization of water-insoluble dye in soap solutions: Effects of added salts, J. Am. Chem. Soc., 68, 1731, 10.1021/ja01213a016 · DOI
  53. Gerry, 1977, The effect of fluorination on surfactant aggregation number and dye solubilization efficiency, J. Colloid Interf. Sci., 62, 556, 10.1016/0021-9797(77)90106-0 · DOI
  54. Nishikido, 1977, Mixed micelles of polyoxyethylene-type nonionic and anionic surfactants in aqueous solutions, J. Colloid Interf. Sci., 60, 242, 10.1016/0021-9797(77)90284-3 · DOI
  55. Tokiwa, 1968, Solubilization behavior of a polyoxyethylene sulfate type of surfactant in connection with the micellar charge, J. Phys. Chem., 72, 4331, 10.1021/j100858a075 · DOI
  56. Murphy, 2004, Surfactant-facilitated crystallization of dihydrate carbamazepine during dissolution of anhydrous polymorph, J. Pharm. Sci., 93, 449, 10.1002/jps.10496 · DOI
  57. Zana, R., and Xia, J. (2004). Gemini Surfactants, Marcel Dekker. · DOI
  58. Menger, 2000, Gemini surfactants, Angew. Chem. Int. Ed., 39, 1906, 10.1002/1521-3773(20000602)39:11<1906::AID-ANIE1906>3.0.CO;2-Q · DOI
  59. Gharanjig, 2011, Solubility of two disperse dyes derived from n-alkyl and n-carboxylic acid naphthalimides in the presence of gemini cationic surfactants, J. Surfactants Deterg., 14, 381, 10.1007/s11743-011-1253-8 · DOI
  60. Bahrami, 2007, Dynamic adsorption of gemini and conventional cationic surfactants onto polyacrylonitrile, Colloids Surf. A., 307, 121, 10.1016/j.colsurfa.2007.05.011 · DOI
  61. Holmberg, 2012, Cationic ester-containing gemini surfactants: Determination of aggregation numbers by time-resolved fluorescence quenching, J. Colloid Interf. Sci., 376, 126, 10.1016/j.jcis.2012.02.053 · DOI
  62. Holmberg, 2008, Cationic ester-containing gemini surfactants: Adsorption at tailor-made surfaces monitored by SPR and QCM, Langmuir, 24, 6140, 10.1021/la800009b · DOI
  63. Holmberg, 2010, Cationic ester-containing gemini surfactants: Physical—Chemical properties, Langmuir, 26, 9276, 10.1021/la1001336 · DOI
  64. Jacobs, 1973, The role of polar head structure in dye solubilization by cationic surfactants, J. Colloid Interf. Sci., 43, 105, 10.1016/0021-9797(73)90353-6 · DOI
  65. Jacobs, 1976, The effect of hydroxyl functionality in the polar head on surfactant aggregation number and dyesolubilization efficiency, J. Colloid Interf. Sci., 56, 255, 10.1016/0021-9797(76)90251-4 · DOI
  66. Anacker, 1977, Group VA effects on surfactant aggregation number and dye solubilization efficiency, J. Colloid Interf. Sci., 60, 514, 10.1016/0021-9797(77)90316-2 · DOI
  67. Anton, 1994, Solubilization by polysoaps, Colloid Polym. Sci., 272, 1118, 10.1007/BF00652381 · DOI
  68. Hinchliffe, 2004, Density functional studies of the dipole polarizabilities of substituted stilbene, azoarene and related push-pull molecules, Int. J. Mol. Sci., 5, 224, 10.3390/i5050224 · DOI
  69. Ikeda, 1989, Physicochemical properties of α, ω-type bolaform surfactant in aqueous solution. Eicosane-1,20-bis(triethylammonium bromide), Colloid Polym. Sci., 267, 825, 10.1007/BF01410122 · DOI
  70. Imae, 1986, Solubilization of a water-insoluble dye in aqueous solutions of dodecyltrimethylammonium halides, and its relation to micelle size and shape, J. Colloid Interf. Sci., 109, 567, 10.1016/0021-9797(86)90338-3 · DOI
  71. Ozeki, 1985, The difference in solubilization power between spherical and rodlike micelles of dodecyldimethylammonlum chloride in aqueous solutions, J. Phys. Chem., 89, 5088, 10.1021/j100269a040 · DOI
  72. Datyner, 1978, The solubilization of disperse dyes by dispersing agents at 127 °C, J. Soc. Dye. Colour., 94, 256, 10.1111/j.1478-4408.1978.tb03417.x · DOI
  73. Swe, 2006, Solubilization of selected polycyclic aromatic compounds by nonionic surfactants, J. Surfactant Deterg., 9, 237, 10.1007/s11743-006-5003-2 · DOI
  74. Ikeda, 1980, Micelle molecular weight of dodecyldimethylammonium chloride in aqueous solutions, and the transition of micelle shape in concentrated NaCl solutions, J. Colloid Interf. Sci., 73, 27, 10.1016/0021-9797(80)90117-4 · DOI
  75. Ozeki, 1980, The viscosity behavior of aqueous NaCl solutions of dodecyldimethylammonium chloride and the flexibility of its rod-like micelle, J. Colloid Interf. Sci., 77, 219, 10.1016/0021-9797(80)90434-8 · DOI
  76. Goddard, 2002, Polymer/surfactant interaction: Interfacial aspects, J. Colloid Interf. Sci., 256, 228, 10.1006/jcis.2001.8066 · DOI
  77. Hansson, 1996, Surfactant-polymer interactions, Curr. Opin. Colloid Interf. Sci., 1, 604, 10.1016/S1359-0294(96)80098-7 · DOI
  78. Nizri, 2005, Solubilization of hydrophobic molecules in nanoparticles formed by polymer—Surfactant interactions, J. Colloid Interf. Sci., 291, 169, 10.1016/j.jcis.2005.04.109 · DOI
  79. Ridell, 2002, Influence of counterion on the interaction of dodecyl sulfates and cellulose ethers, J. Colloid Interf. Sci., 247, 381, 10.1006/jcis.2001.8151 · DOI
  80. Bahadur, 1988, Interaction studies of styrene-ethylene oxide block copolymers with ionic surfactants in aqueous solution, Colloid Surf., 29, 343, 10.1016/0166-6622(88)80146-X · DOI
  81. Ananthapadmanabhan, 1985, Fluorescence and solubilization studies of polymer-surfactant systems, Colloid Surf., 13, 63, 10.1016/0166-6622(85)80006-8 · DOI
  82. Sudbeck, 1991, Dye solubilization in polyelectrolyte-micelle complexes, J. Colloid Interf. Sci., 142, 512, 10.1016/0021-9797(91)90081-I · DOI
  83. Anghel, 2007, The aggregation of nonionic surfactants in the presence of poly(methacrylic acid), Colloid Polym. Sci., 285, 771, 10.1007/s00396-006-1617-1 · DOI
  84. Leung, 1985, A study of polycation-anionic surfactant systems, Colloid Surf., 13, 47, 10.1016/0166-6622(85)80005-6 · DOI
  85. Saito, 1971, Interactions of anionic surfactants with nonionic polymers. comparison of guanidinium, tetraalkylammonium, and alkali metal ions as counterions, J. Colloid Interf. Sci., 37, 154, 10.1016/0021-9797(71)90275-X · DOI
  86. Holmberg, 1996, Phase conditions, hydrodynamic features and salt influence in the polymer-amphiphile interaction for the EHEC/SDS/water system, Colloid Polym. Sci., 274, 836, 10.1007/BF00654741 · DOI
  87. Persson, 1996, On the characterization principles of some technically important water-soluble nonionic cellulose derivatives. Part II: Surface tension and interaction with a surfactant, Carbohydr. Polym., 29, 119, 10.1016/0144-8617(96)00010-0 · DOI
  88. Winnik, 1996, Fluorescence methods in the study of the interactions of surfactants with polymers, Colloid Surf. A, 118, 1, 10.1016/0927-7757(96)03733-8 · DOI
  89. Barbero, 2009, Characterization of monomeric and gemini cationic amphiphilic molecules by fluorescence intensity and anisotropy, Dye. Pigment., 83, 396, 10.1016/j.dyepig.2009.06.013 · DOI
  90. Edwards, 1991, Solubilization of polycyclic aromatic hydrocarbons in micellar nonionic surfactant solutions, Environ. Sci. Technol., 25, 127, 10.1021/es00013a014 · DOI
  91. Dar, 2007, Mixed micelle formation and solubilization behavior toward polycyclic aromatic hydrocarbons of binary and ternary cationic-nonionic surfactant mixtures, J. Phys. Chem. B, 111, 3122, 10.1021/jp066926w · DOI
  92. Barry, 1976, Solubilization of hydrocortisone, dexamethasone, testosterone and progesterone by long-chain polyoxyethylene surfactants, J. Pharm. Pharmaceut., 28, 210, 10.1111/j.2042-7158.1976.tb04133.x · DOI
  93. Tornblom, 1997, Effect of solubilization of aliphatic hydrocarbons on size and shape of rodlike C16TABr micelles studied by 2H NMR relaxation, J. Phys. Chem. B, 101, 6028, 10.1021/jp970899f · DOI
  94. Halle, 1989, The state of water in nonionic surfactant solutions and lyotropic phases, J. Chem. Soc. Faraday Trans. 1, 85, 1049, 10.1039/f19898501049 · DOI
  95. Muto, 1988, The efficiency of solubilization in mixed micelles of nonionic and anionic surfactants, J. Colloid Interf. Sci., 124, 632, 10.1016/0021-9797(88)90200-7 · DOI

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Metadata

Authors
Tehrani-Bagha, A., & Holmberg, K.
Venue
Materials
Publisher
MDPI AG
Published
2013-02-21
Volume
6
Issue
2
Pages
580-608
ISSN
1996-1944
DOI
10.3390/ma6020580
PMC
PMC5452102
Cited by
287
References
0
Language
en
Licence
creativecommons.org/licenses/by/3.0/ (vor)

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