Abstract
Two series of quaternary cationic surfactant were synthesized by reaction of 8-hydroxyquinoline and 2-hydroxypyridine with long chain alkyl halides (dodecyl, tetradecyl- and hexadecyl-bromide). Surface tension was measured in aqueous solution for different concentrations at 25 °C. Various surface properties of the synthesized surfactants were evaluated, particularly critical micelle concentration (CMC), efficiency (ΠCMC) as well as maximum surface excess (Γmax) and minimum surface area (A min). Micellization and adsorption in liquid/air interfaces thermodynamics were investigated. The synthesized cationic surfactants were evaluated for their biocidal activity. All compounds prepared showed good antibacterial and antifungal activities.
Similar content being viewed by others
References
Badawi AM, Marzibani MM, Haroun B, Soliman H (1983) Quaternary ammonium salts of potential biological activity. Curr Sci 52(24):1169–1171
Andrew J, Mc B, Ruth GL, Louiss EM, Carl C, Peter Gt (2004) Effects of quaternary-ammonium based formulation on bacterial community dynamics and antimicrobial susceptibility. Appl Environ Microbiol 70(6):3449–3456
Mahmud SA, Ismail DA, Ghazy EA (2007) Surface properties and biological activity of select cationic surfactants. J Surfactants Detergents 10(4):191–194
Shen AY, Chen CP, Roffler S (1999) A chelating agent possessing cytotoxicity and antimicrobial activity: 7-morpholinomethyl-8-hydroxyquinoline. Life Sci 64(9):813–825
Bych JS, Middlesev NJ (1975) Antimicrobial hydroxyquinoline, ethylene-acrylic polymer composition. U.S. Patent 3,872,128
Eric F, Scriven V, Murugan R (2005) Pyridine and pyridine derivatives, Kirk-Othmer encyclopedia of chemical technology
Soldatenkov AT, Levov AN, Mobio IG, Polyakova EV, Kutyakov SV, Le Tuan An AI, Komarova KB, Polyanskii EI, Andreeva L (2004) Synthesis and biological activity of N- and O-acyl derivatives of 2,6-diphenyl-4-hydroxypiperidines and tetrahydropyridines. Heterocycl comp 35(10)
Ismail DA, Mohamed AS, Mohamed MZ (2004) Synthesis of some new quaternary ammonium compounds: evaluation of their surface properties and solubilization activity. Trans Egypt Soc Chem Eng 30(2):1503–1511
Cooper RE (1972) In: Kavanagen FW (ed) Analytical microbiology, vols I, II. Academic press, New York
Gad EAM, El-Sukkary MMA, Ismail DA (1997) Surface and thermodynamic parameters of sodium N-acyl sarcosinate solutions. J Am Oil Chem Soc 74:34
El-Sukary MMA, Ismail DA, Morsy SMI (2001) Preparation of some tourine derivatives from alkylhalo esters and evaluating them as surface active agents. Egypt J Petroleum 11(5):51–66
Mohamed AS, Mohamed MZ, Ismail DA (2004) Alanine-based surfactants: synthesis and some surface properties. J Surfactants Detergents 7(4):415–419
Mohamed MZ, Ismail DA, Mohamed AS (2005) Synthesis and evaluation of new amphiphilic polyethylene glycol-based triblock copolymer surfactants. J Surfactants Detergents 8(4):175–180
Augusta S, Gruber HF, Streichsbier F (2003) Synthesis and antibacterial activity of immobilized quaternary ammonium salts. J Appl Polymer Sci 53(9):1149–1163
Negm NA, Morsy SMI, Said MM (2005) Biological activity of some Mannich base cationic derivatives. Bioorg Med Chem 13:5921–5926
Badawi AM, Mekawi MA, Mohamed AS, Mohamed MZ, Khowdairy MM (2007) Surface and biological activity of some novel cationic surfactants. J Surfactants Detergents 10(4):243–25
Author information
Authors and Affiliations
Corresponding author
About this article
Cite this article
Ahmed, S.M., Ismail, D.A. Synthesis and Biological Activity of 8-Hydroxyquinoline and 2-Hydroxypyridine Quaternary Ammonium Salts. J Surfact Deterg 11, 231–235 (2008). https://doi.org/10.1007/s11743-008-1078-2
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11743-008-1078-2