Micellar and Surface Properties of Cationic-Cationic Binary Surfactant Mixtures: Synergistic Interactions and Solubility Enhancement of Anthracene

Micellar and Surface Properties of Cationic-Cationic Binary Surfactant Mixtures: Synergistic Interactions and Solubility Enhancement of Anthracene

The micellar and surface behaviors of decylammonium chloride (DACl) in presence of L-alanine hydrochloride decylester (L-ADE) and L-alanine hydrochloride dodecylester (L-ADDE) at various mole fractions were investigated by conductivity and surface tension measurements. From the conductivity measurements, the critical micelle concentration (CMC), the degree of counter-ion ionization (α) and standard Gibbs energy of micellization (ΔG°mic) were investigated for both pure and binary mixtures. The molecular interaction parameter (β) and the micellar mole fraction (XmDACl) for mixed micelle formation by DACl/L-ADE (C10-C10) and DACl/L-ADDE (C10-C12) were calculated using the regular solution equation proposed by Rubingh. The ideal values of CMC (CMCideal) and the micellar mole fraction (XmDACl(ideal)) were also obtained for mixed micelle according to the pseudo phase theoretical models. The negative β values showed that there were synergistic interactions for all compositions of DACl/L-ADE and DACl/L-ADDE mixed systems. From the surface tension measurements, adsorption parameters such as the surface excess concentration (Γmax), minimum surface tension at the CMC, efficiency in the surface tension reduction (pC20), standard Gibbs energy of adsorption (ΔG°ads), and minimum area per head group of a molecule (Amin) in pure, mixed and their ideal values were also determined. The results indicated that the synergism and attractive interactions in the studied binary mixtures depend on the chain length of the cationic L-alanine ester and their mole fractions in the mixed system. The solubilization capacity of pure DACl and its mixed system with L-ADE and L-ADDE towards anthracene were determined and discussed in terms of molar solubilization ratio (MSR). Based on the MSR values, the solubility enhancement was found for anthracene in DACl/L-ADE and DACl/L-ADDE mixed systems.

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  • [1] M.J. Rosen, Surfactants and Interfacial Phenomena, John Wiley & Sons Ltd., New Jersey, pp. 1–30, 400, 44, 83, 121, 2004.
  • [2] K. Holmberg, D. O. Shah, M. J. Schwuger, Handbook of Applied Surface and Colloid Chemistry, John Wiley & Sons Ltd., England, pp.509–512, pp. 55, 2002.
  • [3] T. Geng, C. Zhang, Y. Jiang, H. Ju, Y. Wang, “Synergistic effect of binary mixtures contained newly cationic surfactant: Interaction, aggregation behaviors and application properties,” Journal of Molecular Liquids, vol. 232, pp. 36–44, 2017.
  • [4] S. Singh, K. Parikh, S. Kumar, V.K. Aswal, S. Kumar, “Spacer nature and composition as key factors for structural tailoring of anionic/cationic mixed gemini micelles: Interaction and solubilization studies,” Journal of Molecular Liquids, vol. 279, pp. 108–119, 2019.
  • [5] A. Bera, K. Ojha, A. Mandal, “Synergistic Effect of Mixed Surfactant Systems on Foam Behavior and Surface Tension,” Journal of Surfactants and Detergents, vol. 16, pp. 621–630, 2013.
  • [6] K. Singh, D. G. Marangoni, “Synergistic interactions in the mixed micelles of cationic gemini with zwitterionic surfactants: The pH and spacer effect,” Journal of Colloid and Interface Science, vol. 315, pp. 620–626, 2007.
  • [7] D. Calvo, J. L. Ruiz, M. Valiente, “Phase equilibria of mixtures of surfactants and viscoelastic properties of the liquid crystal phases,” Fluid Phase Equilibria, vol. 425, pp. 358–364, 2016.
  • [8] T. Cosgrove, “Colloid Science Principles, Methods and Applications,” John Wiley &Sons Ltd, U.K., pp. 65, 71, 2010.
  • [9] T. Morisue, Y. Moroi, O. Shibata, “Solubilization of Benzene, Naphthalene, Anthracene, and Pyrene in Dodecyl ammonium Trifluoroacetate Micelles,” Journal of Physical Chemistry, vol. 98, pp. 12995–13000, 1994.
  • [10] P. A. Bhat, A. A. Dar, and G. M. Rather, “Solubilization Capabilities of Some Cationic, Anionic, and Nonionic Surfactants toward the Poorly Water-Soluble Antibiotic Drug Erythromycin,” Journal of Chemical Engineering and Data, vol. 53, pp. 1271–1277, 2008.
  • [11] J. Lakra, D. Tikariha, T. Yadav, M. L. Satnami, K. K. Ghosh, “Study of Solubility Efficiency of Polycyclic Aromatic Hydrocarbons in Single Surfactant Systems,” Journal of Surfactants and Detergents, vol. 16, pp. 957–966, 2013.
  • [12] S. Padasala, K. Kuperkarb, P. Bahadura, “Solubilisation study of water-insoluble dye in cationic single/dimeric surfactant micelles: effect of headgroup, non-polar tail, and spacer chain in aqueous and salt solution,” Coloration Technology, vol. 132, pp. 217–221, 2016.
  • [13] Y. Moroi, K. Mitsunobu, T. Morisue, Y. Kadobayashi, M. Sakai, “Solubilization of Benzene, Naphthalene, Anthracene, and Pyrene in 1-Dodecanesulfonic Acid Micelle,” Journal of Physical Chemistry, vol. 99, pp. 2372–2376, 1995.
  • [14] J. Wei, G. Huang, L. Zhu, S. Zhao, C. An a, Y. Fan, “Enhanced aqueous solubility of naphthalene and pyrene by binary and ternary Gemini cationic and conventional nonionic surfactants,” Chemosphere, vol. 89, pp. 1347–1353, 2012.
  • [15] M. Panda, K.-Din, “Solubilization of polycyclic aromatic hydrocarbons by gemini–conventional mixed surfactant systems,” Journal of Molecular Liquids, vol. 187, pp. 106–113, 2013.
  • [16] N. Fatma, M. Panda, W. H. Ansari, K.-Din “Solubility enhancement of anthracene and pyrene in the mixtures of acleavable cationic gemini surfactant with conventional surfactants of different polarities,” Colloids and Surfaces A: Physicochemical and Engineering Aspects, vol. 467, pp. 9–17, 2015.
  • [17] Y. Liang, S. Zhang, H. Li, X. Mao, Y. Li, X. Xie, J. Ren, G. Li, R. Lian, “Solubilization of polycyclic aromatic hydrocarbons by novel ester-bonded Gemini prolinol-based surfactant and its binary mixtures with conventional surfactants,” Journal of Dispersion Science and Technology, vol. 41, pp. 1–10, 2019.
  • [18] P. S. Sales, R. H. de Rossi, M. A. Fernández, “Different behaviours in the solubilization of polycyclic aromatic hydrocarbons in water induced by mixed surfactant solutions,” Chemosphere, vol. 84, pp. 1700–1707, 2011.
  • [19] J. Weia, G. Huanga, H. Yua, C. An, “Efficiency of single and mixed Gemini/conventional micelles on solubilization of phenanthrene,” Chemical Engineering Journal, vol. 168, pp. 201–207, 2011.
  • [20] K.-Dina, M. Shafia, P. A. Bhat, A. A. Dar, “Solubilization capabilities of mixtures of cationic Gemini surfactant with conventional cationic, nonionic and anionic surfactants towards polycyclic aromatic hydrocarbons,” Journal of Hazardous Materials, vol. 167, pp. 575–581, 2009.
  • [21] L. Zhu, S. Feng, “Synergistic solubilization of polycyclic aromatic hydrocarbons by mixed anionic–nonionic surfactants,” Chemosphere, vol. 53, pp. 459–467, 2003.
  • [22] M. Acimis, C. Ocak, S. Ozacar and K. Gocmen, “Effect of the thickness of the hydrophobic bilayer on the helical twisting power in micellar nematic liquid crystals,” New Journal of Chemistry, vol. 26, pp. 427–432, 2002.
  • [23] M. Acimis, “A type II aqueous cholesteric lyomesophase,” Canadian Journal of Chemistry, vol. 58, pp. 1533–1541, 1980.
  • [24] A. A. Dar, G. M. Rather, and A. R. Das, “Mixed Micelle Formation and Solubilization Behavior toward Polycyclic Aromatic Hydrocarbons of Binary and Ternary Cationic-Nonionic Surfactant Mixtures,” J. Phys. Chem. B, vol. 111, pp. 3122–3132, 2007.
  • [25] T.-S. Choi, Y. Shimizu, H. Shirai, K. Hamada, “Solubilization of disperse dyes in cationic gemini surfactant micelles,” Dyes and Pigments, vol. 45, pp. 145–152, 2000.
  • [26] J. Weia, G. Huanga, H. Yua, C. An, “Efficiency of single and mixed Gemini/conventional micelles on solubilization of phenanthrene,” Chemical Engineering Journal, vol. 168, pp. 201–207, 2011.
  • [27] K. D. Danov, P. A. Kralchevsky, K. P. Ananthapadmanabhan, “Micelle–monomer equilibria in solutions of ionic surfactants and in ionic–nonionic mixtures:A generalized phase separation model,” Advances in Colloid and Interface Science, vol. 206, pp. 17–45, 2014.
  • [28] E. B. Olutas, T. Taskesen, N. B. Kartal, “Double-Tailed Single-Head Amino Acid-Based Chiral Cationic Amphiphilic Molecules: Synthesis, Characterization, and Physicochemical Properties,” Journal of Surfactants and Detergents, vol. 23, pp. 153–168, 2020.
  • [29] B. Janczuk, J. A. M. Sierra, M. L. Gonzalez-Martin, J.M. Bruque, W. Wojcik, “Properties of Decylammonium Chloride and Cesium Perfluorooctanoate at Interfaces and Standard Free Energy of Their Adsorption,” Journal of Colloid and Interface Science, vol. 192, pp. 408–414, 1997.
  • [30] M. L. Gonzalez-Martin, B. Janczuk, J.A. Me´ndez-Sierra, J.M. Bruque, “Volumetric properties of the decylammonium chloride and cesium perfluorooctanoate from density measurements,” Colloids and Surfaces A: Physicochemical and Engineering Aspects, vol. 148, pp. 213–221, 1999.
  • [31] N. Azum, A. Z. Naqvi, M. Akram, K.-Din, “Properties of Mixed Aqueous Micellar Solutions Formed by Cationic Alkanediyl-r,ω-bis(tetradecyldimethylammonium bromide) and Alkyltrimethylammonium Bromides: Fluorescence and Conductivity Studies,” Journal of Chemical Engineering and Data, vol. 54, pp. 1518–1523, 2009.
  • [32] Z.-X. Chen, S.-P. Deng, X.-K. Li, “Micellization and synergistic interaction of binary surfactant mixtures based on sodium nonylphenol polyoxyethylene ether sulfate,” Journal of Colloid and Interface Science, vol. 318, pp. 389–396, 2008.
  • [33] S. P. Moulik, Md. E. Haque, P. K. Jana, A. R. Das, “Micellar Properties of Cationic Surfactants in Pure and Mixed States,” Journal of Physical Chemistry, vol. 100, pp. 701–708, 1996.
  • [34] K.-Din, M. A. Rub, A. Z. Naqvi, “Mixed Micelle Formation between Amphiphilic Drug Amitriptyline Hydrochloride and Surfactants (Conventional and Gemini) at 293.15-308.15 K,” Journal of Physical Chemistry, vol. 114, pp. 6354–6364, 2010.
  • [35] E. B. Olutas “Interactions in mixed micellar systems comprising chiral cationic amino acid based and conventional anionic surfactants,” Journal of Molecular Liquids vol. 275, pp. 126–135, 2019.
  • [36] P. M. Holland, D. N. Rubingh, “Nonideal multicomponent mixed micelle model,” Journal of Physical Chemistry, vol. 84, pp. 1984–1990, 1983.
  • [37] S.K. Mehta, Bhawna, “Significant effect of polar head group of surfactants on the solubilization of Zein in mixed micellar (SDS–DDAB) media,” Colloids and Surfaces B: Biointerfaces, vol. 81, pp. 74–80, 2010.
  • [38] R. Kakehashi, M. Shizuma, S. Yamamura, T. Takeda, “Mixed micelles containing sodium oleate: the effect of the chain length and the polar head group,” Journal of Colloid and Interface Science, vol. 279, pp. 253–258, 2004.
  • [39] A. Ali, U. Farooq, S. Uzair, R. Patel, “Conductometric and tensiometric studies on the mixed micellar systems of surface-active ionic liquid and cationic surfactants in aqueous medium,” Journal of Molecular Liquids, vol. 223, pp. 589–602, 2016.
  • [40] E. B. Olutas, M. Acimis, “Thermodynamic parameters of some partially fluorinated and hydrogenated amphiphilic enantiomers and their racemates in aqueous solution,” Journal of Chemical Thermodynamics, vol. 47, pp. 144–153, 2012.
  • [41] C. M. C. Faustino, A. R Calado, L. B. Garcia−Rio, “Gemini Surfactants−Protein Interactions: Effect of pH, Temperature, and Surfactant Stereochemistry,” Biomacromolecules, vol. 10, pp. 2508–2514, 2009.
  • [42] S. Javadian, H. Gharibi, Z. Bromand, B. Sohrabi, “Electrolyte effect on mixed micelle and interfacial properties of binary mixtures of cationic and nonionic surfactants,” Journal of Colloid and Interface Science, vol. 318, pp. 449–456, 2008.
  • [43] N. A. Negma, M. R. Mishrif, D. E. Mohamed, “Vanillin based cationic surfactants mixed systems: Micellization and interfacial interaction behaviors in presence of nonionic conventional surfactant,” Colloids and Surfaces A: Physicochemical and Engineering Aspects, vol. 480, pp. 122–129, 2015.
  • [44] N. Fatma, W. H. Ansari, M. Panda, K.-Din, “A Systematic Study of Mixed Surfactant Solutions of a Cationic Ester-Bonded Dimeric Surfactant with Cationic, Anionic and Nonionic Monomeric Surfactants in Aqueous Media,” Journal of Surfactants and Detergents, vol. 16, pp. 609–620, 2013.
  • [45] M. Yang, J. Ke, Q. Zhang, X. He “Effects of Mixed Surfactant on Enhancing High Concentration Anthracene and Pyrene Removal from Contaminated Soil,” Water Air Soil Pollut., vol. 230: 121, pp. 1–12, 2019.