Synthesis of glycerol-based pyridinium surfactants and appraisal of their properties

Industrial and Engineering Chemistry Research

Volumn 48, Issue 3, 2009, Pages 1673-1677

  Singh, Sukhprit ^a   Bhadani, Avinash ^a   Kataria, Hardeep ^a   Kaur, Gurcharan ^a   Kamboj, Raman ^a  

^a GURU NANAK DEV UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIUM COMPOUNDS; BIOCOMPATIBILITY; DYES; GLYCEROL; PARAFFINS; SURFACE PROPERTIES;

PYRIDINIUM; TETRADECYL TRIMETHYL AMMONIUM BROMIDES;

CATIONIC SURFACTANTS;

EID: 61549128154     PISSN: 08885885     EISSN: None     Source Type: Journal    
DOI: 10.1021/ie801737m     Document Type: Article

References (30)

1. Bartuška, W. R.; Silverman, P. Henna hair coloring and/or conditioning compositions, U.S. Patent 4,183,366, January 15, 1980.
2. Hatanaka, K.; Hirayama, T. Liquid cleansing cosmetics containing carboxyl group-containing acidic polymers and nitrogen heterocyclic cationic surfactants.Jàpanese Patent JP 2005187338, July 14, 2005.
3. Kenji, N.; Nakamura, K. Antimicrobial and deodorant cosmetic brush and method of producing the same.U.S. Patent 6,604,531, August 12, 2003.
4. Free, M. L. Understanding the effect of surfactant aggregation on corrosion inhibition of mild steel in acidic medium. Corros. Sci. 2002, 44, 2865-2870.
5. Shah, S. S.; Fahey, W. F.; Oude, B. A. Corrosion inhibitors, for distribution of petroleum and petroleum products, consisting of a pyridinium compound and a quaternary ammonium salt, U.S. Patent 5,336,441, August 9, 1994.
6. Chigwada, G.; Wang, D.; Wilkie, C. A. Polystyrene nanocomposites based on quinolinium and pyridinium surfactants. Polym. Degrad. Stab. 2006, 91, 848-855.
7. Zaragoza-Contreras, E. A.; Rodriguez-Gonzalez, R. J.; Navoarro-Rodriguez, D. Emulsion polymerization of styrene using a new series of rigid rodlike cationic surfactants. Macromol. Chem. Phys. 1999, 200, 828-833.
8. Koopal, L. K.; Goloub, T.; Keizer, A.; De Marianna, P. The effect of cationic surfactants on wetting colloid stability and flotation of silica. Colloids Surf. A 1999, 151, 15-25,
9. Prince, A. K.; Sukonick, B. Polyfluoroisoalkoxyalkyl pyridinium salts, U.S. Patent 3,674,798, July 4, 1972.
10. 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.
11. Pernak, J.; Branicka, M. The properties of 1-alkoxymethyl-3- hydroxypyridinium and 1-alkoxymethyl-3-dimethylaminopyridinium chlorides. J. Surfactants Deterg. 2003, 6, 119-123.
12. Haider, J.; Kondaiah, P.; Bhattacharya, S. Synthesis and Antibacterial Properties of Novel Hydrolyzable Cationic Amphiphiles. Incorporation of Multiple Head Groups Leads to Impressive Antibacterial Activity. J. Med. Chem. 2005, 48, 3823-3831.
13. Zhao, T.; Sun, G. Synthesis and characterization of antimicrobial cationic surfactants: aminopyridinium salts. J. Surfactants Deterg. 2006, 9, 325-330.
14. Karande, P.; Mitragotri, S. High Throughput Screening of Transdermal Formulations. Pharm. Res. 2002, 19, 665-660.
15. Pop, E. Targeting penicillins to the central nervous system: chemical delivery systems and redox analogs. Adv. Drug Delivery Rev. 1994, 14, 211-226.
16. Hies, M. A.; Seitz, W. A.; Ghiviriga, I.; Johnson, B. H.; Miller, A.; Thompson, E. B.; Balaban, A. T. Pyridinium cationic lipids in gene delivery: a structure-activity correlation study. J. Med Chem. 2004, 47, 3744-3754.
17. van der Woude, I.; Wagenaar, A.; Meekel, A. A. P.; ter Beest, M. B. A.; Rutters, M. H. J.; Engberts, J. B. F. N.; Hoekstra, D. Novel pyridinium surfactants for efficient, nontoxic in vitro gene delivery. Proc. Natl. Acad. Sci., U.S.A. 1997, 94, 1160-1165.
18. Goto, M.; Momota, A.; Ono, T. DNA extraction by cationic reverse micelles. J. Chem. Eng. Jpn. 2004, 37 (5), 662-668.
19. Rai, H.; Ohtsuka, S.; Nishiyama, M.; Senoo, K. Optimizing bead-beating DNA extraction protocol from environmental samples with use of surfactant and heat treatment,PCT Int. Appl. WO 2005073377, August 11, 2005.
20. Suzuki, M.; Ishida, Y.; Komatsubara, S.; Kamakami, F.; Kamamura, Y. Extraction method for plant DNA,Japanese Patent JP 11169170, June 29, 1999.
21. Gunstone, F. D.; Padley, F. B. Lipid Technologies and Application; Marcel Dekker: New York, 1997.
22. Karsa, D. R.; Porter, M. R. Biodegradability of Surfactants; Blackie Academic & Professional Publishers: London, 1995.
23. Pagliaro, M.; Rossi, M. The Future of Glycerol: New Uses of a Versatile Raw Material; RSC Green Chemistry Series; Royal Society for Chemistry; Cambridge, U.K., 2008.
24. Zhou, C.-H.; Beltramini, J. N.; Fan, Y.-X.; Lu, G. Q. Chemoselective catalytic conversion of glycerol as a biorenewable source to value commodity chemicals. Chem. Soc. Rev. 2008, 37, 527-549.
25. Singh, S.; Bhadani, A.; Kamboj, R. Syntiiesis of β-Bromoglycerol monoethers from α-olefins. Ind. Eng. Chem. Res. 2008, 47, 8090-8094.
26. Bakshi, M. S. Cetylpyridinium chloride-tetradecylammonium bromide mixed micelles in ethylene glycol-water and diethylene glycol-water mitures. J. Chem. Soc., Faraday Trans. 1997, 93 (22), 4004-4008.
27. Madaan, P.; Tyagi, V. K. Quaternary Pyridinium Salts: A Review. J. Oleo Sci. 2008, 57 (4), 197-215.
28. Vyas, S. M.; Turánek, J.; Knötigová, P.; Kan̂á, A.; Kvardová, V.; Koganti, V.; Rankin, S. E.; Knutsonc, B. L.; Lehmler, H.-J. Synthesis and biocompatibility evaluation of partially fluorinated pyridinium bromides. New J. Chem. 2006, 30, 944-951.
29. Zhao, X.; Zhang, Z.; Pan, F.; Waigh, T. A.; Lu, J. R. Plasmid DNA complexation with phosphorylcholine diblock copolymers and its effect on cell transfection. Langmuir 2008, 24, 6681-6888.
30. Paria, S.; Yuet, P. K. Effects of Chain Length and Electrolyte on Adsorption of n-Alkyl Pyridinium Bromide Surfactants at Sand-Water Interfaces. Ind. Eng. Chem. Res. 2006, 45, 712-718.