Formation of Mixed Micelles of the Environmentally Acceptable Oxy-Diester-Linked Gemini Surfactants with Brij 58
-
Manorama Panda
and Mohammad Kamil
Abstract
Three oxy-diester-linked cationic gemini surfactants (2,2′-[(oxybis(ethane-1,2-diyl))bis(oxy)]bis(N-alkyl-N,N-dimethyl-2-oxoethanaminium) dichloride, Cm-DEG-Cm (m = 12, 14, 16), were synthesized. The physicochemical properties of the gemini surfactants and their mixtures with Brij 58 were studied by surface tension measurements at various mole fractions and 30°C. The critical micelle concentration (CMC) of the gemini surfactants are smaller than that of their corresponding single-chain counterparts having the same number of carbon atoms in the hydrophobic tail versus polar head. At all investigated compositions, the experimentally obtained CMC values of the surfactant mixtures are smaller than the CMCideal (ideal CMC – CMC of the solution at ideal state); the lower CMC of the mixed systems compared to those the individual surfactants and the negative β values (for both the mixed micelles and monolayers) indicate a synergistic interaction among both the surfactant components. The interaction parameters (βm and βσ) of the mixed surfactant systems were evaluated by using theoretical models. Negative values of β imply an overall attractive force in the mixed state. Also, the free excess energy of mixing was found to be negative for all the systems.
Kurzfassung
Es wurden drei kationische, mit Oxy-Diester verknüpfte Gemini-Tenside (2,2′-[(Oxybis-(ethan-1,2-diyl))-bis-(oxy)]-bis-(N-alkyl-N,N-dimethyl-2-oxoethanaminium)dichlorid, Cm-DEG-Cm (m = 12, 14, 16) synthetisiert. Die physikalisch-chemischen Eigenschaften der Gemini-Tenside und ihrer Mischungen mit Brij 58 wurden mittels Oberflächenspannungsmessungen bei verschiedenen Molenbrüchen und bei 30°C untersucht. Die kritische Mizellenbildungskonzentration (CMC) der Gemini-Tenside ist geringer als die der Tenside, die eine gleiche Anzahl an Kohlenstoffatomen im hydrophoben Teil gegenüber dem polaren Kopf besitzen. Die experimentell erhaltenen CMC-Werte der Tensidmischungen sind für alle untersuchten Zusammensetzungen kleiner als die ideale CMC (CMCideal = CMC der Lösung im idealen Zustand); die im Vergleich zu den einzelnen Tensiden niedrigeren CMC der gemischten Systeme und die negativen β-Werte (sowohl für die gemischten Mizellen als auch für die Monoschichten) deuten auf synergistische Wechselwirkungen zwischen den beiden Tensidkomponenten hin. Die Wechselwirkungsparameter βm und βσ der Mischtensidsysteme wurden unter Verwendung theoretischer Modelle bewertet. Die negativen Werte von β implizieren insgesamt eine Anziehungskraft im gemischten Zustand. Außerdem wurde gefunden, dass die freie Überschussenergie des Mischens für alle Systeme negativ ist.
References
1. Rosen, M. J. and Tracy, D. J.: Gemini surfactants, J. Surf. Detergents1 (1998) 547–554. 10.1007/s11743-998-0057-8Search in Google Scholar
2. Kabir-ud-Din, Rub, M. A. and Naqvi, A. Z.: Mixed micelle formation between amphiphilic drug amitriptyline hydrochloride and surfactants (conventional and gemini) at 293.15–308.15 K, J. Phys. Chem. B114 (2010) 6354–6364. 20423055 10.1021/jp100123rSearch in Google Scholar PubMed
3. Siddiqui, H., Kamil, M., Panda, M. and Kabir-ud-Din: Solubilization of phenanthrene and fluorene in equimolar binary mixtures of gemini/conventional surfactants, Chin. J. Chem. Eng.22 (2014) 1009–1015. 10.1016/j.cjche.2014.06.028Search in Google Scholar
4. Kralova, K., Sersen, F., Devinsky, F. and Lacko, I.: Photosynthesis-inhibiting effects of cationic biodegradable gemini surfactants, Tenside Surf. Detergents47 (2010) 288–293. 10.3139/113.110079Search in Google Scholar
5. Ansari, W. H., Fatma, N., Panda, M. and Kabir-ud-Din: Solubilization of polycyclic aromatic hydrocarbons by novel biodegradable cationic gemini surfactant ethane-1,2-diyl bis(N N-dimethyl-N-hexadecylammoniumacetoxy) dichloride and its binary mixtures with conventional surfactants, Soft Matter9 (2013) 1478–1487. 10.1039/C2SM26926KSearch in Google Scholar
6. Fatma, N., Panda, M., Ansari, W. H. and Kabir-ud-Din: Environment-friendly ester bonded gemini surfactant: Mixed micellization of 14-E2-14 with ionic and nonionic conventional surfactants, J. Mol. Liq.211 (2015) 247–255. 10.1016/j.molliq.2015.06.064Search in Google Scholar
7. Gao, Z., Tai, S., Zhang, Q., Zhao, Y., Lu, B., Ge, Y., Huang, L. and Tang, X.: Synthesis and surface activity of biquaternary ammonium salt gemini surfactants with ester bond, Wuhan Univ. J. Natural Sci.13 (2008) 227–231. 10.1007/s11859-008-0219-9Search in Google Scholar
8. Banno, T., Kawada, K. and Matsumura, S.: Creation of novel green and sustainable gemini-type cationics containing carbonate linkages, J. Surfactants Deterg.13 (2010) 387–398. 10.1007/s11743-010-1224-5Search in Google Scholar
9. Shukla, D. and Tyagi, V. K.: Development of cleavable surfactants, Tenside Surf. Detergents47 (2010) 7–12. 10.3139/113.110046Search in Google Scholar
10. Kuo, C.-F. J., Lin, L.-H., Dong, M.-Y., Chang, W.-S. and Chen, K.-M.: Preparation and properties of new ester-linked cleavable gemini surfactants, J. Surfactants Deterg.14 (2011) 195–201. 10.1007/s11743-010-1232-5Search in Google Scholar
11. Lundberg, D., Stjerndahl, M. and Holmberg, K.: Mixed micellar systems of cleavable surfactants, Langmuir21 (2005) 8658–8663. 16142944 10.1021/la051162hSearch in Google Scholar PubMed
12. Fatma, N., Ansari, W. H., Panda, M. and Kabir-ud-Din: Mixed micellization behavior of gemini (cationic ester-bonded) surfactants with conventional (cationic, anionic and nonionic) surfactants in aqueous medium, Z. Phys. Chem.227 (2013) 133–149. 10.1524/zpch.2013.0288Search in Google Scholar
13. Bhadani, A., Endo, T., Sakai, K., Sakai, H. and Abe, M.: Synthesis and dilute aqueous solution properties of ester functionalized cationic gemini surfactants having different ethylene oxide units as spacer, Colloid Polym. Sci.292 (2014) 1685–1692. 10.1007/s00396-014-3233-9Search in Google Scholar
14. Wu, Y., Iglauer, S., Shuler, P., Tang, Y. and GoddardW. A.: Alkyl polyglycoside-sorbitan ester formulations for improved oil recovery, Tenside Surf. Detergents, 47 (2010) 280–287. 10.3139/113.110078Search in Google Scholar
15. Wang, X., Wang, J., Wang, Y., Ye, J., Yan, H. and Thomas, R. K.: Properties of mixed micelles of cationic gemini surfactants and nonionic surfactant triton X-100: Effects of the surfactant composition and the spacer length, J. Colloid Interface Sci.286 (2005) 739–746. 15897092 10.1016/j.jcis.2005.01.084Search in Google Scholar PubMed
16. Kabir-ud-Din, Sheikh, M. S., Bhat, P. A. and Dar, A. A.: Solubilization capabilities of mixtures of cationic gemini surfactant with conventional cationic, nonionic and anionic surfactants towards polycyclic aromatic hydrocarbons, J. Hazard. Mater.167 (2009) 575–581. 19232468 10.1016/j.jhazmat.2009.01.022Search in Google Scholar PubMed
17. Panda, M. and Kabir-ud-Din: Study of surface and solution properties of gemini-conventional surfactant mixtures and their effects on solubilization of polycyclic aromatic hydrocarbons, J. Mol. Liq.163 (2011) 93–98. 10.1016/j.molliq.2011.08.002Search in Google Scholar
18. Fatma, N., Ansari, W. H., Panda, M. and Kabir-ud-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, J. Surf. Detergents16 (2013) 609–620. 10.1007/s11743-013-1448-2Search in Google Scholar
19. Bhadani, A., Shrestha, R. G., Koura, S., Endo, T., Sakai, K., Abe, M. and Sakai, H.: Self-aggregation properties of new ester-based gemini surfactants and their rheological behavior in the presence of cosurfactant – monolaurin, Colloids Surf. A, Physicochem. Eng. Aspects461 (2014) 258–266. 10.1016/j.colsurfa.2014.08.001Search in Google Scholar
20. Siddiqui, H., Kamil, M. and Fatima, N.: Surface and solution properties of single and mixed gemini/conventional micelles on solubilization of polycyclic aromatic hydrocarbons, Ind. J. Chem. Technol.22 (2015) 194–200.Search in Google Scholar
21. Panda, M. and Kabir-ud-Din: Solubilization of polycyclic aromatic hydrocarbons by gemini–conventional mixed surfactant systems, J. Mol. Liq.187 (2013) 106–113. 10.1016/j.molliq.2013.06.008Search in Google Scholar
22. SchulzP. C., Rodríguez, J. L., MinardiR. M., SierraM. B., MoriniM. A., Are the mixtures of homologous surfactants ideal?J. Colloid Interface Sci.303 (2006) 264–271. 16887137 10.1016/j.jcis.2006.07.012Search in Google Scholar
23. Panda, M. and Kamil, M.: Interaction of oxy-diester-linked cationic gemini surfactants with nonionic amphiphiles in aqueous medium Colloid Polym. Sci.295 (2017) 2363–2371. 10.1007/s00396-017-4203-9Search in Google Scholar
24. Clint, J. H.: Micellization of mixed nonionic surface active agents, J. Chem. Soc. Faraday Trans. 1, 71 (1975) 1327–1334. 10.1039/F19757101327Search in Google Scholar
25. Rubingh, D. N. in: K.L.Mittal (Ed.), Mixed Micelle Solutions; Solution Chemistry of Surfactants, vol. 1, Plenum Press, New York, 1979, p. 337. 10.1007/978-1-4615-7880-2Search in Google Scholar
26. Holland, P. M. and Rubingh, D. N.: Nonideal multicomponent mixed micelle model, J. Phys. Chem.87 (1983) 1984–1990. 10.1021/j100234a030Search in Google Scholar
27. MotomuraK., YamanakaM., AratonoM., Thermodynamic consideration of the mixed micelle of surfactants, Colloid Polym. Sci.262 (1984) 948–955. 10.1007/BF01490027Search in Google Scholar
28. Bakshi, M. S. and Singh, K.: Synergistic interactions in the mixed micelles of cationic gemini with zwitterionic surfactants: Fluorescence and Krafft temperature studies, J. Colloid Interface Sci.287 (2005) 288–297. 15914176 10.1016/j.jcis.2005.01.099Search in Google Scholar
29. Singh, K. and Marangoni, D. G.: Synergistic interactions in the mixed micelles of cationic gemini with zwitterionic surfactants: The pH and spacer effect, J. Colloid Interface Sci.315 (2007) 620–626. 17761190 10.1016/j.jcis.2007.06.062Search in Google Scholar
30. Gu, B. and Rosen, M. J.: Surface concentrations and molecule interactions in cationic-anionic mixed monolayers at various interfaces, J. Colloid Interface Sci.129 (1989) 537–553. 10.1016/0021-9797(89)90468-2Search in Google Scholar
31. Liu, L. and Rosen, M. J.: The interaction of some novel diquaternary gemini surfactants with anionic surfactants, J. Colloid Interface Sci.179 (1996) 454–459. 10.1006/jcis.1996.0237Search in Google Scholar
32. Zhou, Q. and Rosen, M. J.: Molecular interactions of surfactants in mixed monolayers at the air/aqueous solution interface and in mixed micelles in aqueous media: the regular solution approach, Langmuir, 19 (2003) 4555–4562. 10.1021/la020789mSearch in Google Scholar
33. Chattoraj, D. K. and Birdi, K. S.: Adsorption and the Gibbs surface excess, Plenum, New York, 1984. 10.1007/978-1-4615-8333-2Search in Google Scholar
34. Alami, E., Beinert, G., Marie, P. and Zana, R.: Alkanediyl-α,ω-bis(dimethylalkylammonium bromide) surfactants. 3. Behavior at the air-water interface, Langmuir, 9 (1993) 1465–1467. 10.1021/la00030a006Search in Google Scholar
35. Zana, R.: Dimeric and oligomeric surfactants. Behavior at interfaces and in aqueous solution: a review, Adv. Colloid Interface Sci.97 (2002) 205–253. 10.1016/s0001-8686(01)00069-0Search in Google Scholar
© 2018, Carl Hanser Publisher, Munich
Articles in the same Issue
- Contents/Inhalt
- Contents
- Review Article
- Synthesis, Properties and Applications of Anionic Phosphate Ester Surfactants: A Review
- Detergent Ingredients
- Biological Surfactants vs. Polysorbates: Comparison of Their Emulsifier and Surfactant Properties
- Environmental Chemistry
- Green and Efficient Reverse Micellar Extraction and Recovery of Mixed Ionic Dyes from Textile Effluent
- Physical Chemistry
- Thermodynamic and Interfacial Properties of Cationic Gemini Surfactant in the Presence of Alcohols
- Research of Binary Surfactant Mixtures Based on N-Lauroyl Sarcosinate
- Surface and Interfacial Properties of Mono and Didodecyl Diphenyl Ether Disulfonates
- Application
- Adsorption and Surface Properties of Mixtures of Fatty Acid Methyl Ester Ethoxylates and Sodium Dodecylbenzene Sulfonate
- Synthesis
- Synthesis and Interfacial Tensions of Sodium p-Dimethyl Dodecylbenzene Sulfonates
- Synthesis of 4-Hydroxy-4-(4-nitrophenyl)butan-2-one using p-Nitro Benzaldehyde and Acetone in Aqueous Micellar Media using L-Proline
- Novel Surfactants
- Foam and Rheological Properties of a Kind of Extended Surfactants
- Formation of Mixed Micelles of the Environmentally Acceptable Oxy-Diester-Linked Gemini Surfactants with Brij 58
Articles in the same Issue
- Contents/Inhalt
- Contents
- Review Article
- Synthesis, Properties and Applications of Anionic Phosphate Ester Surfactants: A Review
- Detergent Ingredients
- Biological Surfactants vs. Polysorbates: Comparison of Their Emulsifier and Surfactant Properties
- Environmental Chemistry
- Green and Efficient Reverse Micellar Extraction and Recovery of Mixed Ionic Dyes from Textile Effluent
- Physical Chemistry
- Thermodynamic and Interfacial Properties of Cationic Gemini Surfactant in the Presence of Alcohols
- Research of Binary Surfactant Mixtures Based on N-Lauroyl Sarcosinate
- Surface and Interfacial Properties of Mono and Didodecyl Diphenyl Ether Disulfonates
- Application
- Adsorption and Surface Properties of Mixtures of Fatty Acid Methyl Ester Ethoxylates and Sodium Dodecylbenzene Sulfonate
- Synthesis
- Synthesis and Interfacial Tensions of Sodium p-Dimethyl Dodecylbenzene Sulfonates
- Synthesis of 4-Hydroxy-4-(4-nitrophenyl)butan-2-one using p-Nitro Benzaldehyde and Acetone in Aqueous Micellar Media using L-Proline
- Novel Surfactants
- Foam and Rheological Properties of a Kind of Extended Surfactants
- Formation of Mixed Micelles of the Environmentally Acceptable Oxy-Diester-Linked Gemini Surfactants with Brij 58