Characterization, surface properties and biological activity of new prepared cationic surfactants

Ismail Aiad; Mohamed M. El-Sukkary; E.A. Soliman; Moshira Y. El-Awady; Samy M. Shaban

Journal of Industrial and Engineering Chemistry, Vol.20, No.4, 1633-1640, July, 2014

DOI10.1016/j.jiec.2013.08.010 Export Citation

Characterization, surface properties and biological activity of new prepared cationic surfactants

Ismail Aiad, Mohamed M. El-Sukkary, E.A. Soliman¹, Moshira Y. El-Awady, and Samy M. Shaban^†

Petrochemical Department, Egyptian Petroleum Research Institute, Ain Shams University, Cairo, Egypt
¹Faculty of Science, Ain Shams University, Cairo, Egypt

E-mail:

Three cationic surfactants were prepared. A condensation reaction between dimethylaminopropylamine(DMAPA) and benzaldehyde was performed. The produced Schiff base was quaternization with three fatty alkyl bromide with different carbon chain length separately to form the desired cationic surfactants. The chemical structure of synthesized cationic surfactants was confirmed by FTIR, 1H NMR and mass spectroscopy. It was found that the chemical structure of prepared compounds has an effect on surface properties, where increasing the hydrophobic chain length decrease the values of CMC, Tmax while Amin value was increased. The thermodynamic parameters showed that adsorption and micellization processes are spontaneous. It is clear that the prepared cationic surfactants at first tend to adsorb at surface, then it aggregate to form micelle. The prepared surfactants showed good biological activity against gram positive and negative bacteria and fungi in the following order of II (C12) > I (C10) > III (C16). The serial dilution method was used to evaluate the inhibiting effect of these compounds on the sulfate reducing bacteria growth.

Keywords:Cationic surfactants;Quaternary ammonium salts;Surface parameters;Thermodynamic parameters;Biological activity

[References]

Rafiquee MZA, Saxena N, Khan S, Quraishi MA, Mater. Chem. Phys., 107(2-3), 528 (2008)
Jarudilokkul S, Paulsen E, Stuckey DC, Bioseparation, 9(2), 81 (2000)
Pernaka J, Kalewskaa J, Ksycin’skab H, Cybulskib J, Eur. J. Med. Chem., 36, 899 (2001)
Serres E, Vicendo P, Perez E, Noel T, Rico-Lattes I, Langmuir, 15(20), 6956 (1999)
Huntsman, Dimethylaminopropylamine. Technical Bulletin. www.huntsman.-com/performance_chemicals/media/DMAPA.pdf, 1995 (searched 3.05.04).
Speight EL, Beck MH, Lawrence CM, Contact Dermatitis, 28, 49 (1993)
Brubaker RE, Muranko HJ, Smith DB, Beck GJ, Scovel G, J. Occup. Med., 21(10), 688 (1979)
Erskine PT, Newbold R, Roper J, Coker A, Protein Sci., 8, 1250 (1999)
Rashad AE, Ali MA, Nucleotides, 25, 17 (2006)
Young ME, Alakomi HL, Fortune I, Gorbushina AA, Krumbein WE, Maxwell I, McCullagh C, Robertson P, Saarela M, Valero J, Vendrell M, Environ. Geol., 56, 631 (2008)
Cerchiaro G, Ferreira AM, Teixeira AB, Magalhaes HM, Polyhedron, 25, 2055 (2006)
Erk B, Dilmac A, Baran Y, Balaban A, Synth. React. Inorg. Met. Org. Chem., 10, 30 (2000)
El-Sukkary MMA, Aiad I, Syed NA, El-Azab WIM, J. Surfact. Deterg., 11, 129 (2008)
Chatterjee A, Maiti S, Sanyal SK, Moulik SP, Langmuir, 18(8), 2998 (2002)
El-sukkary MMA, Aiad I, Deeb A, El-awady MY, Ahmed HM, Shaban SM, Pet. Sci. Technol., 28, 1158 (2010)
Mousli R, Tazerouti A, J. Surfact. Deterg., 14, 65 (2011)
Shuichi M, Kazayasu I, Sadao Y, Kazuo K, Tsuyoshi Y, J. Am. Oil Chem. Soc., 67(12), 996 (1991)
Rosen MJ, Zhu ZH, J. Am. Oil Chem. Soc., 65, 663 (1987)
Aiad I, EL-Sukkary MM, El-Deeb A, El-Awady MY, Shaban SM, J. Surfact. Deterg., 16, 243 (2013)
Mahmoud SA, Ismail DA, Ghazy EA, J. Surfact. Deterg., 10, 191 (2007)
Aiad I, EL-Sukkary MM, El-Deeb A, El-Awady MY, Shaban SM, J. Surfact. Deterg., 15, 359 (2012)
Nagamune H, Maeda T, Ohkura K, Yamamoto K, Nakajima M, Kourai H, Toxicol. In Vitro, 14, 139 (2000)
Viscardi G, Quagliotto P, Barolo C, Savarino P, Barni E, Fisciaro E, J. Org. Chem., 65(24), 8197 (2000)
Pernak J, Kalewska J, Ksycinska H, Cybulski J, Eur. J. Med. Chem., 36, 899 (2001)
Birnie CR, Malamud D, Schnaare RL, Antimicrob. Agents Chemother., 44, 2514 (2000)
Campanac C, Pineau L, Payard A, Baziard-Mouysset G, Roques C, Antimicrob. Agents Chemother., 46, 1469 (2002)
Koch A, Clin. Microbiol. Rev., 16(4), 673 (2003)
Walsh F, Amyes S, Curr. Opin. Microbiol., 7(5), 439 (2004)
Chernomordik I, Kozlov MM, Zimmerberg J, J. Membr. Biol., 146, 1 (1995)
Saier MH, Enzymes in Metabolic Pathways. A Comparative Study of Mechanism, Structure, Evolution, and Control, Harper & Row, New York, 1987.

[Referenced By]

[1] Rafiquee MZA, Saxena N, Khan S, Quraishi MA, Mater. Chem. Phys., 107(2-3), 528 (2008)

[2] Jarudilokkul S, Paulsen E, Stuckey DC, Bioseparation, 9(2), 81 (2000)

[3] Pernaka J, Kalewskaa J, Ksycin’skab H, Cybulskib J, Eur. J. Med. Chem., 36, 899 (2001)

[4] Serres E, Vicendo P, Perez E, Noel T, Rico-Lattes I, Langmuir, 15(20), 6956 (1999)

[5] Huntsman, Dimethylaminopropylamine. Technical Bulletin. www.huntsman.-com/performance_chemicals/media/DMAPA.pdf, 1995 (searched 3.05.04).

[6] Speight EL, Beck MH, Lawrence CM, Contact Dermatitis, 28, 49 (1993)

[7] Brubaker RE, Muranko HJ, Smith DB, Beck GJ, Scovel G, J. Occup. Med., 21(10), 688 (1979)

[8] Erskine PT, Newbold R, Roper J, Coker A, Protein Sci., 8, 1250 (1999)

[9] Rashad AE, Ali MA, Nucleotides, 25, 17 (2006)

[10] Young ME, Alakomi HL, Fortune I, Gorbushina AA, Krumbein WE, Maxwell I, McCullagh C, Robertson P, Saarela M, Valero J, Vendrell M, Environ. Geol., 56, 631 (2008)

[11] Cerchiaro G, Ferreira AM, Teixeira AB, Magalhaes HM, Polyhedron, 25, 2055 (2006)

[12] Erk B, Dilmac A, Baran Y, Balaban A, Synth. React. Inorg. Met. Org. Chem., 10, 30 (2000)

[13] El-Sukkary MMA, Aiad I, Syed NA, El-Azab WIM, J. Surfact. Deterg., 11, 129 (2008)

[14] Chatterjee A, Maiti S, Sanyal SK, Moulik SP, Langmuir, 18(8), 2998 (2002)

[15] El-sukkary MMA, Aiad I, Deeb A, El-awady MY, Ahmed HM, Shaban SM, Pet. Sci. Technol., 28, 1158 (2010)

[16] Mousli R, Tazerouti A, J. Surfact. Deterg., 14, 65 (2011)

[17] Shuichi M, Kazayasu I, Sadao Y, Kazuo K, Tsuyoshi Y, J. Am. Oil Chem. Soc., 67(12), 996 (1991)

[18] Rosen MJ, Zhu ZH, J. Am. Oil Chem. Soc., 65, 663 (1987)

[19] Aiad I, EL-Sukkary MM, El-Deeb A, El-Awady MY, Shaban SM, J. Surfact. Deterg., 16, 243 (2013)

[20] Mahmoud SA, Ismail DA, Ghazy EA, J. Surfact. Deterg., 10, 191 (2007)

[21] Aiad I, EL-Sukkary MM, El-Deeb A, El-Awady MY, Shaban SM, J. Surfact. Deterg., 15, 359 (2012)

[22] Nagamune H, Maeda T, Ohkura K, Yamamoto K, Nakajima M, Kourai H, Toxicol. In Vitro, 14, 139 (2000)

[23] Viscardi G, Quagliotto P, Barolo C, Savarino P, Barni E, Fisciaro E, J. Org. Chem., 65(24), 8197 (2000)

[24] Pernak J, Kalewska J, Ksycinska H, Cybulski J, Eur. J. Med. Chem., 36, 899 (2001)

[25] Birnie CR, Malamud D, Schnaare RL, Antimicrob. Agents Chemother., 44, 2514 (2000)

[26] Campanac C, Pineau L, Payard A, Baziard-Mouysset G, Roques C, Antimicrob. Agents Chemother., 46, 1469 (2002)

[27] Koch A, Clin. Microbiol. Rev., 16(4), 673 (2003)

[28] Walsh F, Amyes S, Curr. Opin. Microbiol., 7(5), 439 (2004)

[29] Chernomordik I, Kozlov MM, Zimmerberg J, J. Membr. Biol., 146, 1 (1995)

[30] Saier MH, Enzymes in Metabolic Pathways. A Comparative Study of Mechanism, Structure, Evolution, and Control, Harper & Row, New York, 1987.