QSPR study of critical micelle concentrations of nonionic surfactants

Industrial and Engineering Chemistry Research

Volumn 47, Issue 23, 2008, Pages 9687-9695

  Katritzky, Alan R ^a   Pacureanu, Liliana M ^a,b   Slavov, Svetoslav H ^a   Dobchev, Dimitar A ^a,c,d   Karelson, Mati ^c  

^a University of Florida ^*  (United States)

^b ACADEMY OF ROMANIAN SCIENTISTS   (Romania)

^c TALLINN UNIVERSITY OF TECHNOLOGY   (Estonia)

^d MolCode Ltd   (Estonia)

Author keywords

[No Author keywords available]

Indexed keywords

DATA SETS; DESCRIPTORS; DIPOLE INTERACTIONS; HETERO ATOMS; MOLECULAR SHAPES; NONLINEAR PREDICTIVE MODELS; QSPR MODELS; STERIC HINDRANCES;

CHEMICAL REACTIONS; COLLOIDS; CRITICAL MICELLE CONCENTRATION; MICELLES; SURFACE ACTIVE AGENTS;

NONIONIC SURFACTANTS;

EID: 57949097315     PISSN: 08885885     EISSN: None     Source Type: Journal    
DOI: 10.1021/ie800954k     Document Type: Article

References (56)

1. Fuguet, E.; Ràfols, C.; Rosés, B. Critical micelle concentration of surfactants in aqueous buffered and unbuffered systems. Anal. Chim. Acta 2005, 548, 95.
2. Arai, T.; Takasugi, K.; Esumi, K. Micellar properties of nonionic saccharide surfactants with amide linkage in aqueous solution. Colloids Surf. 1996, 119, 81.
3. Paxton, T. R. Adsorbtion of emulsifier on polystyrene and poly(methyl methacrylate) latex particles. J. Colloid Interface Sci. 1969, 31, 19.
4. Perkowski, J.; Mayer, J.; Ledakowicz, S. Determination of critical micelle concentration of non-ionic surfactanys using kinetic approach. Colloids Surf. 1995, 101, 103.
5. Kato, T.; Iwai, M.; Seimiya, T. Micellar growth in mixed anionic/ cationic surfactant solutions: Sodium dodecyl sulfate/octyltrimethylammonium bromide. J. Colloid Interface Sci. 1989, 130, 439.
6. Ray, G. B.; Chakraborty, I.; Moulik, S. P. Pyrene absorbtion can be a convenient method for probing critical micellar concentration (CMC) and indexing micellar polarity. J. Colloid Interface Sci. 2006, 294, 248.
7. Kumar, G.; Kanti, K.; Chandra, B. Physicochemical characteristics of reverse micelles of polyoxyethylene nonyl phenol in different organic solvents. J. Colloid Interface Sci. 2004, 279, 523.
8. Thies, M.; Poschmann, M.; Hinze, U.; Paradies, H. H. Light scattering on micellar solutions of N,N′-butyl-n-alkyl-1,4-diazabicyclo-[2,2,2]-octane derivatives of 3′-O-acylthymidine-5′-phosphates. Colloids Surf. 1995, 101, 159.
9. Huibers, P. D. T.; Lobanov, V. S.; Katritzky, A. R.; Shah, O. D.; Karelson, M. Prediction of critical micelle concentration using a quantitative structure-property relationship approach. 1. Nonionic surfactants. Langmuir 1996, 12, 1462.
10. Huibers, P. D. T.; Lobanov, V. S.; Katritzky, A. R.; Shah, O. D.; Karelson, M. Prediction of critical micelle concentration using a quantitative structure-property relationship approach. 2. Anionic surfactants. J. Colloid Interface Sci. 1997, 187, 113.
11. Li, X.-S.; Lu, J.-E; Liu, J.-C. Studies on UNIQUAC and SAFT equations for nonionic surfactant solutions. Fluid Phase Equilib. 1998, 153, 215.
12. Cheng, J.-S.; Chen, Y.-P. Correlation of critical micelle concentration for aqueous solutions of nonionic surfactants. Fluid Phase Equilib. 2005, 232, 37.
13. Puvada, S.; Blankschtein, D. Thermodynamic description of micellization, phase behavior, and phase separation of aqueous solutions of surfactant mixtures. J. Phys. Chem. 1992, 96, 5567.
14. van Lent, B.; Scheutjens, J. M. H. M. Influence of association on adsorbtion properties of block copolymers. Macromolecules 1989, 22, 1931.
15. Becker, P. Hydrophile-Lipophile Balance: History and recent Developments. J. Dispersion Sci. Technol. 1984, 5, 81.
16. Ravey, J. C.; Gerbi, A.; Stebe, M. J. Comparative study of fluorinated and hydrogenated nonionic surfactants. I. Surface activity properties and critical concentrations. Prog. Colloid Polym. Sci. 1988, 76, 234.
17. Chen, C. C. Molecular thermodynamic model for Gibbs energy of mixing of nonionic surfactant solutions. AIChE J. 1996, 42, 3231.
18. Saunders, R. A.; Platts, J. A. Correlation and prediction of critical micelle concentration using polar surface area and LFER methods. J. Phys. Org. Chem. 2004, 17, 431-138.
19. Yuan, S.; Cai, Z.; Xu, G.; Jiang, Y. Quantitative structure-property relationships of surfactants: prediction of the critical micelle concentration of nonionic surfactants. Colloid Polym. Sci. 2002, 280, 630.
20. Wang, Z.; Li, G.; Zhang, X.; Wang, R.; Lou, A. A quantitative structure-property relationship study for the prediction of critical micelle concentration of nonionic surfactants. Colloids Surf. 2002, 197, 37.
21. Chen, L.-J.; Lin, S.-Y.; Huang, C.-C.; Chen, E.-M. Temperature dependence of critical micelle concentration of polyoxyethylenated nonionic surfactants. Colloids Surf. 1998, 135, 175.
22. Koga, K.; Ohyashiki, T.; Murakami, M.; Kawashima, S. Modification of Ceftibuten transport by the addition of nonionic surfactants. Eur. J. Pharm. Biopharm. 2000, 49, 17.
23. Nakahara, Y.; Kida, T.; Nakatsuji, Y.; Akashi, M. New fluorescence method for determination of the critical micelle concentration by photosensitive monoazacryptand derivatives. Langmuir 2005, 21, 6688.
24. Paddon-Jones, G.; Regismond, S.; Kwetkat, K.; Zana, R. Micellization of nonionic surfactant dimmers and of the corresponding surfactant monomers in aqueous solutions. J. Colloid Interface Sci. 2001, 243, 496.
25. Komorek, U.; Wilk, K. A. Surface and micellar properties of new nonionic Gemini aldonamide-type surfactants. J. Colloid Interface Sci. 2004, 271, 206.
26. Molina-Bolivar, J. A.; Aguiar, J.; Peula-Garcia, J. M.; Ruiz, C. Surface activity, micelle formation, and growth of n-octyl-β-thioglucopyranoside in aqueous solutions at different temperatures. J. Phys. Chem. B 2004, 108, 12813.
27. Mureau, N.; Trabelsi, H.; Guittard, F.; Geribaldi, S. Preparation and evaluation of monodisperse nonionic surfactants based on fluorine-containning dicarbamates. J. Colloid Interface Sci. 2000, 229, 440.
28. 2 - terminal groups: adsorbtion at the surface of aqueous solutions. Langmuir 2001, 17, 7873.
29. Kjellin, U. R. M.; Reimer, J.; Hanson, P. An investigation of dynamic surface tension, critical micelle concentration, and aggregation number of three nonionic surfactants using NMR, time-resolved fluorescence quenching, and maximum bubble pressure tensiometry. J. Colloid Interface Sci. 2003, 262, 506.
30. Castro, M.; Kovensky, J.; Fernandez-Cirelli, A. New family of nonionic Gemini surfactants, determination and analysis of interfacial properties. Langmuir 2002, 18, 2477.
31. Ortona, O.; Vitagliano, V.; Paduano, L.; Costantino, L. Microcalorimetric study of some short-chain nonionic surfactants. J. Colloid Interface Sci. 1998, 203, 477.
32. Gosh, S. K.; Khatua, P. K.; Battacharya, S. C. Characterization of micelles of polyoxyethylene nonylphenol (Igepal) and its complexation with 3,7-diamino-2,8-dimethyl-5-phenylphenazinium chloride. J. Colloid Interface Sci. 2004, 275, 623.
33. Drummond, C. J.; Wells, D. Nonionic lactose and lactitol based surfactants: comparison of some physico-chemical properties. Colloids Surf. 1998, 141, 131.
34. Savelli, M. P.; Van Roekeghem, P.; Douillet, O.; Cavé, G.; Godé, P.; Ronco, G.; Villa, P. Effects of tail alkyl chain length (n), head group structure and junction (Z) on amphiphilic properties of 1-Z-R-D,L-xylitol compounds (R=C n H 2n+l). Int. J. Pharm. 1999, 182, 221.
35. www.hyper.com.
36. Dewar, J. S. M.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. AM1: A new general purpose quantum mechanical molecular model. J. Am. Chem. Soc. 1985, 107, 3902.
37. www.codessa-pro.com.
38. http://www.epa.gov/opptintr/exposure/pubs/episuite.htm.
39. Katritzky, A. R.; Mu, L.; Lobanov, V.; Karelson, M. Correlation of boiling points with molecular structure. 1. A traninig set of 298 diverse organics and a test set of 9 simple inorganics. J. Phys. Chem. 1996, 100, 10400.
40. Katritzky, A. R.; Tamm, K.; Kuanar, M.; Fara, D. C.; Oliferenko, A.; Oliferenko, P.; Huddleston, J. G.; Rogers, R. D. Aqueous biphasic systems. Partitioning of organic molecules: a QSPR treatment. J. Chem. Inf. Comput. Sci. 2004, 44, 136.
41. Katritzky, A. R.; Kuanar, M.; Fara, D. C.; Hur, E.; Karelson, M. The classification of solvents by combining classical QSPR methodology with principal component analysis. J. Phys. Chem. A 2005, 109, 10323.
42. Luèiæ, B.; Bašic, I.; Nadramija, D.; Trinajstiæc, N.; Takahiro, S.; Petrukin, R.; Karelson, M.; Katritzky, A. Correlation of liquid viscosity with molecular structure for organic compounds using different variable selection methods. ARKIVOC 2002, 4, 45.
43. Katritzky, A. R.; Fara, D. C.; Yang, H.; Karelson, M.; Suzuki, T.; Solov'ev, V. P.; Varnek, A. QSPR Modeling of beta-Cyclodextrin Complexation Free Energies. J. Chem. Inf. Comp. Sci. 2004, 44, 529.
44. Katritzky, A. R.; Fara, D. C.; Karelson, M. QSPR of 3-aryloxazolidin-2- one antibacterials. Bioorg. Med. Chem. 2004, 12, 3027.
45. Katritzky, A.; Dobchev, D.; Fara, D.; Karelson, M. QSAR treatment of drugs transfer into human breast milk. Bioorg. Med. Chem. 2005, 13, 1623.
46. Katritzky, A. R.; Oliferenko, A.; Lomaka, A.; Karelson, M. Six membred cyclic ureas as HIV-1 protease inhibitors: a QSAR study based on CODESSA PRO approach. Bioorg. Med. Chem. Lett. 2002, 12, 3453.
47. Beteringhe, A.; Balaban, A. T. QSAR for toxicities of polychlorodibenzofurans, polychlorodibenzo-1,4-dioxins, and polychlorobiphenyls. ARKIVOC 2004, 1, 163.
48. Zefirov, N.; Palyulin, A. Fragmental approach in QSPR. J. Chem. Inf. Comput. Sci. 2002, 42, 1112.
49. Klopman, G.; Zhu, H. Estimation of the aqueous solubility of organic molecules by the group contribution approach. J. Chem. Inf. Comput. Sci. 2001, 41, 439.
50. Trepalin, S. V.; Gerasimenko, V. A.; Kozyukov, A. V.; Savchuk, N. P.; Ivaschenko, A. A. New Diversity Calculations Algorihms Used for Compound Selection. J. Chem. Inf. Comput. Sci. 2002, 42, 249.
51. Bawden, D. Computerized chemical structure handling techniques in structure - activity studies and molecular property prediction. J. Chem. Inf. Comput. Sci. 1983, 23, 14.
52. Karelson, M. In Molecular Descriptors in QSAR/QSPR; J. Wiley & Sons: New York, 2000.
53. Kubinyi, H. QSAR in Drug Design. In Handbook of Chemoinformatics; Gasteiger, J., Ed.; Wiley-VCH: Weinheim, 2003; Vol. 4, pp 1532-1554.
54. Katritzky, A. R.; Kuanar, M.; Dobchev, D.; Vanhoecke, B.; Karelson, M.; Parmar, V.; Stevens, C.; Bracke, M. QSAR modeling of anti - invasive activity of organic compounds using structural descriptors. Bioorg. Med. Chem. 2006, 14, 6933.
55. Katritzky, A. R.; Slavov, S.; Dobchev, D.; Karelson, M. QSAR modeling of the antifungal activity against Candida albicans for a diverse set of organic compounds. Bioorg. Med. Chem., 2008, 16, 7055.
56. Rohrbaugh, R. H.; Jurs, P. C. Descriptions of molecular shape applied in studies of structure/activity and structure/property relationships. Anal. Chim. Acta 1987, 199, 99.