Solubilization of n -alkylbenzenes into gemini surfactant micelles in aqueous medium

Langmuir

Volumn 30, Issue 20, 2014, Pages 5771-5779

  Nakahara, Hiromichi ^a   Kojima, Yui ^a   Moroi, Yoshikiyo ^a   Shibata, Osamu ^a  

^a NAGASAKI INTERNATIONAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CRITICAL MICELLE CONCENTRATION; ENTROPY; FOURIER TRANSFORM INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SOLUBILITY;

CRITICAL MICELLE CONCENTRATION (CMC); EQUILIBRIUM CONCENTRATION; FOURIER TRANSFORM INFRARED; GIBBS ENERGY CHANGE; HYDRODYNAMIC DIAMETER; NUCLEAR OVERHAUSER EFFECT SPECTROSCOPY; TEMPERATURE DEPENDENCE; THERMODYNAMIC PARAMETER;

MICELLES;

BENZENE DERIVATIVE; DECANEDIYL-1,10-BIS(DIMETHYLTETRADECYLAMMONIUM); MICELLE; QUATERNARY AMMONIUM DERIVATIVE; SURFACTANT; WATER;

CHEMISTRY; INFRARED SPECTROSCOPY; MICELLE; SOLUBILITY;

BENZENE DERIVATIVES; MICELLES; QUATERNARY AMMONIUM COMPOUNDS; SOLUBILITY; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; SURFACE-ACTIVE AGENTS; WATER;

EID: 84901427798     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la501519a     Document Type: Article

References (54)

1. Moroi, Y. Micelles: Theoretical and Applied Aspects; Plenum Press: New York, 1992; Chapter 9, p 252.
2. Elworthy, P. H.; Florence, A. T.; Macfarlane, C. B. Solubilization by surface active agents and its application in chemistry and biological sciences; Chapman & Hall: London, 1968.
3. McBain, M. L. E.; Hutchinson, E. Solubilization and related phenomena; Academic Press: New York, 1955.
4. Mitra, S.; Dungan, S. R. Cholesterol solubilization in aqueous micellar solutions of quillaja saponin, bile salts, or nonionic surfactants J. Agric. Food Chem. 2000, 49, 384-394
5. Xiarchos, I.; Doulia, D. Effect of nonionic surfactants on the solubilization of alachlor J. Hazard. Mater. 2006, 136, 882-888
6. 8) micelles Langmuir 2007, 23, 7505-7509
7. Nakamura, S.; Kobayashi, L.; Tanaka, R.; Isoda-Yamashita, T.; Lee, J.; Moroi, Y. Solubilization of n -alkylbenzenes into decanoyl-N-methylglucamide (Mega-10) solution; temperature dependence Colloids Surf., B 2009, 69, 135-140
8. Zheng, G.; Selvam, A.; Wong, J. W. C. Enhanced solubilization and desorption of organochlorine pesticides (OCPs) from soil by oil-swollen micelles formed with a nonionic surfactant Environ. Sci. Technol. 2012, 46, 12062-12068
9. Alamiry, M. A. H.; Benniston, A. C.; Harriman, A. Effect of pressure on the solubilization of a fluorescent merocyanine dye by a nonionic surfactant J. Phys. Chem. B 2012, 116, 253-260
10. Lee, J.; Moroi, Y. Solubilization of n -alkylbenzenes in aggregates of sodium dodecyl sulfate and a cationic polymer of high charge density (II) Langmuir 2004, 20, 6116-6119
11. Mehta, S. K.; Bhawna Significant effect of polar head group of surfactants on the solubilization of Zein in mixed micellar (SDS-DDAB) media Colloids Surf., B 2010, 81, 74-80
12. Mehta, S. K.; Chaudhary, S. Micropartioning and solubilization enhancement of 1,2-bis(bis(4-chlorophenyl) methyl)diselane in mixed micelles of binary and ternary cationic-nonionic surfactant mixtures Colloids Surf., B 2011, 83, 139-147
13. Mehta, S. K.; Chaudhary, S.; Kumar, R.; Bhasin, K. K. Facile solubilization of organochalcogen compounds in mixed micelle formation of binary and ternary cationic-nonionic surfactant mixtures J. Phys. Chem. B 2009, 113, 7188-7193
14. Rao, K. J.; Paria, S. Solubilization of naphthalene in the presence of plant-synthetic mixed surfactant systems J. Phys. Chem. B 2008, 113, 474-481
15. Mehling, T.; Kloss, L.; Ingram, T.; Smirnova, I. Partition coefficients of ionizable solutes in mixed nonionic/ionic micellar systems Langmuir 2013, 29, 1035-1044
16. Menger, F. M.; Littau, C. A. Gemini surfactants: a new class of self-assembling molecules J. Am. Chem. Soc. 1993, 115, 10083-10090
17. Menger, F. M.; Littau, C. A. Gemini-surfactants: synthesis and properties J. Am. Chem. Soc. 1991, 113, 1451-1452
18. Zana, R. Gemini (dimeric) surfactants Curr. Opin. Colloid Interface Sci. 1996, 1, 566-571
19. Alami, E.; Levy, H.; Zana, R.; Skoulios, A. Alkanediyl-,ω- bis(dimethylalkylammonium bromide) surfactants. 2. Structure of the lyotropic mesophases in the presence of water Langmuir 1993, 9, 940-944
20. Alami, E.; Beinert, G.; Marie, P.; Zana, R. Alkanediyl-,ω- bis(dimethylalkylammonium bromide) surfactants. 3. Behavior at the air-water interface Langmuir 1993, 9, 1465-1467
21. Zana, R.; Benrraou, M.; Rueff, R. Alkanediyl-,ω- bis(dimethylalkylammonium bromide) surfactants. 1. Effect of the spacer chain length on the critical micelle concentration and micelle ionization degree Langmuir 1991, 7, 1072-1075
22. Badea, I.; Verrall, R.; Baca-Estrada, M.; Tikoo, S.; Rosenberg, A.; Kumar, P.; Foldvari, M. In vivo cutaneous interferon-gene delivery using novel dicationic (gemini) surfactant-plasmid complexes J. Gene Med. 2005, 7, 1200-1214
23. Chevalier, Y. New surfactants: new chemical functions and molecular architectures Curr. Opin. Colloid Interface Sci. 2002, 7, 3-11
24. Kirby, A. J.; Camilleri, P.; Engberts, J. B. F. N.; Feiters, M. C.; Nolte, R. J. M.; Söderman, O.; Bergsma, M.; Bell, P. C.; Fielden, M. L.; García Rodríguez, C. L.; Guédat, P.; Kremer, A.; McGregor, C.; Perrin, C.; Ronsin, G.; van Eijk, M. C. P. Gemini surfactants: new synthetic vectors for gene transfection Angew. Chem., Int. Ed. 2003, 42, 1448-1457
25. Rosenzweig, H. S.; Rakhmanova, V. A.; MacDonald, R. C. Diquaternary ammonium compounds as transfection agents Bioconjugate Chem. 2001, 12, 258-263
26. Zana, R. Dimeric and oligomeric surfactants. Behavior at interfaces and in aqueous solution: a review Adv. Colloid Interface Sci. 2002, 97, 205-253
27. Bernheim-Groswasser, A.; Zana, R.; Talmon, Y. Sphere-to-cylinder transition in aqueous micellar solution of a dimeric (gemini) surfactant J. Phys. Chem. B 2000, 104, 4005-4009
28. Danino, D.; Talmon, Y.; Zana, R. Alkanediyl-,ω- bis(dimethylalkylammonium bromide) surfactants (dimeric surfactants). 5. Aggregation and microstructure in aqueous solutions Langmuir 1995, 11, 1448-1456
29. Viscardi, G.; Quagliotto, P.; Barolo, C.; Savarino, P.; Barni, E.; Fisicaro, E. Synthesis and surface and antimicrobial properties of novel cationic surfactants J. Org. Chem. 2000, 65, 8197-8203
30. Zana, R.; Talmon, Y. Dependence of aggregate morphology on structure of dimeric surfactants Nature 1993, 362, 228-230
31. 122Br J. Colloid Interface Sci. 2006, 300, 749-754
32. Tehrani-Bagha, A. R.; Singh, R. G.; Holmberg, K. Solubilization of two organic dyes by cationic ester-containing gemini surfactants J. Colloid Interface Sci. 2012, 376, 112-118
33. Matsuoka, K.; Takeuchi, E.; Takahashi, M.; Kitsugi, S.; Honda, C.; Endo, K. Solubilization of n -alkylbenzene and n -perfluoroalkylbenzene in hydrogenated and fluorinated surfactants micelles J. Colloid Interface Sci. 2009, 333, 641-645
34. Nakahara, H.; Hasegawa, A.; Uehara, S.; Akisada, H.; Shibata, O. Solution properties of gemini surfactant of decanediyl-1-10-bis (dimethyltetradecylammonium bromide) in aqueous medium J. Oleo. Sci. 2013, 62, 905-912
35. Chen, J.; Xue, H.; Yao, Y.; Yang, H.; Li, A.; Xu, M.; Chen, Q.; Cheng, R. Effect of surfactant concentration on the complex structure of poly(N -isopropylacrylamide)/sodium n -dodecyl sulfate in aqueous solutions Macromolecules 2012, 45, 5524-5529
36. m surfactant micelles J. Phys. Chem. B 2014, 118, 179-188
37. Nakamura, S.; Kobayashi, L.; Tanaka, R.; Isoda-Yamashita, T.; Motomura, K.; Moroi, Y. Solubilization of n -alkylbenzenes into decanoyl- N -methylglucamide (Mega-10) solution Langmuir 2008, 24, 15-18
38. Eastman, J. W.; Rehfeld, S. J. Interaction of the benzene molecule with liquid solvents. Fluorescence quenching parallels (0-0) ultraviolet absorption intensity J. Phys. Chem. 1970, 74, 1438-1443
39. Takeuchi, M.; Moroi, Y. Solubilization of n -alkylbenzenes into 1-dodecanesulfonic acid micelles Langmuir 1995, 11, 4719-4723
40. Takeuchi, M.; Moroi, Y. Solubilization of n -alkylbenzenes into lithium 1-perfluoroundecanoate micelles J. Colloid Interface Sci. 1998, 197, 230-235
41. Tewari, Y. B.; Miller, M. M.; Wasik, S. P.; Martire, D. E. Aqueous solubility and octanol/water partition coefficient of organic compounds at 25.0°C J. Chem. Eng. Data 1982, 27, 451-454
42. Sanemasa, I.; Araki, M.; Deguchi, T.; Nagai, H. Solubility measurements of benzene and the alkylbenzenes in water by making use of solute vapor Bull. Chem. Soc. Jpn. 1982, 55, 1054-1062
43. Myrdal, P.; Ward, G. H.; Dannenfelser, R.-M.; Mishra, D.; Yalkowsky, S. H. AQUAFAC 1: Aqueous functional group activity coefficients; application to hydrocarbons Chemosphere 1992, 24, 1047-1061
44. Doi, Y.; Kawashima, Y.; Matsuoka, K.; Moroi, Y. O/W Emulsion of n -alkylbenzene/ionic surfactant/water systems J. Phys. Chem. B 2004, 108, 2594-2599
45. Haynes, W. M. CRC Handbook of Chemistry and Physics, 91 st ed.; CRC Press: Boca Raton, 2010; p 2610.
46. 13C chemical shift measurements and 2D NOESY spectroscopy Colloid Polym. Sci. 2010, 288, 653-663
47. Aguiar, J.; J.A, M.-B.; Peula-García, J. M.; Carnero Ruiz, C. Thermodynamics and micellar properties of tetradecyltrimethylammonium bromide in formamide-water mixtures J. Colloid Interface Sci. 2002, 255, 382-390
48. Ozeki, S.; Ikeda, S. The difference in solubilization power between spherical and rodlike micelles of dodecyldimethylammonium chloride in aqueous solutions J. Phys. Chem. 1985, 89, 5088-5093
49. Ikeda, S.; Maruyama, Y. Solubilization of a water-insoluble dye in aqueous sodium halide solutions of dodecylpyridinium halides: effects of counterion species of ionic micelles J. Colloid Interface Sci. 1994, 166, 1-5
50. Kim, J.-H.; Domach, M. M.; Tilton, R. D. Effect of electrolytes on the pyrene solubilization capacity of dodecyl sulfate micelles Langmuir 2000, 16, 10037-10043
51. Kahlweit, M.; Busse, G.; Winkler, J. Electric conductivity in microemulsions J. Chem. Phys. 1993, 99, 5605-5614
52. 2 mixtures J. Chem. Phys. 2001, 115, 8575-8582
53. Tamura, T.; Takeuchi, Y.; Kaneko, Y. Influence of surfactant structure on the drainage of nonionic surfactant foam films J. Colloid Interface Sci. 1998, 206, 112-121
54. 8) Bull. Chem. Soc. Jpn. 2005, 78, 604-610