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Received May 13, 2018
Accepted July 26, 2018
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Synthesis, interfacial properties, and antimicrobial activity of a new cationic gemini surfactant
School of Chemical Engineering, Institute of Engineering, Suranaree University of Techno, Nakhon Ratchasima 30000, Thailand 1Faculty of Medical Science, Nakhon Ratchasima College, Nakhon Ratchasima 30000, Thailand 2School of Preclinical Sciences, Institute of Science, Suranaree University of Technology, Nakhon Ratchasima 30000, Thailand
atthaphon@sut.ac.th
Korean Journal of Chemical Engineering, November 2018, 35(11), 2313-2320(8), 10.1007/s11814-018-0133-6
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Abstract
Tetramethylene-1,4-bis(N,N-dodecylammonium bromide), cationic gemini surfactant, (12-4-12) was first synthesized with an one-step and shortened procedure and its interfacial and antimicrobial properties were compared with a conventional single-chain cationic surfactant, cetyltrimethylammonium bromide (CTAB). The interfacial and thermodynamic properties of both surfactants reveal that critical micelle concentration (CMC) of this novel synthetic cationic dimeric surfactant is lower than that of cationic monomeric surfactant at almost 15 times of its magnitude, which is due to the increase in hydrophobicity of the surfactant molecules by having dual hydrocarbon chains. In comparison with CTAB, the produced compound 12-4-12 yields much better interfacial and thermodynamic properties. The antimicrobial activities of the synthesized gemini surfactant were tested against eight strains of bacteria, as well as two strains of fungi. The results showed that both 12-4-12 compound and CTAB exhibited higher inhibitory effects on the growth of Gram-positive bacteria and fungi than that of Gram-negative bacteria. The minimum inhibitory concentrations in molar of 12-4-12 against all tested Gram-negative bacteria were lower than those of CTAB, which is hypothetically due to the lower HLB together with smaller CMC values of our gemini surfactant.
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Lechuga M, Fernandez-Serrano M, Jurado E, Nunez-Olea J, Rios F, Ecotoxicol. Environ. Saf., 125, 1 (2016)
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Davies JT, in Proceedings of 2nd International Congress Surface Activity Vol. Butterworths (1957).
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Manko D, Zdziennicka A, Janczuk B, Colloids Surf. B: Biointerfaces, 114, 170 (2014)
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Wang XY, Wang JB, Wang YL, Ye JP, Yan HK, Thomas RK, J. Phys. Chem. B, 107(41), 11428 (2003)
Borse MS, Devi S, Adv. Colloid Interface Sci., 123, 387 (2006)
Ghosh K, Quagliotto P, Indian J. Chem., Sect. A: Inorg., Bioinorg. Phys., Theor. Anal. Chem., 48, 1522 (2009)
Tsuchido T, Svarachorn A, Soga H, Takano M, Antimicrob. Agents Chemother., 34, 78 (1990)
Wu G, Yang Q, Long M, Guo L, Li B, Meng Y, Zhang A, Wang H, Liu S, Zou L, J. Antibiot., 68, 661 (2015)
Ishikawa S, Matsumura Y, Yoshizako F, Tsuchido T, J. Appl. Microbiol., 92(2), 261 (2002)
Vaara M, Antimicrob. Agents Chemother., 37, 2255 (1993)
Fatma N, Panda M, Kabir-ud-Din, Beg M, J. Mol. Liq., 222, 390 (2016)
Migahed MA, Negm NA, Shaban MM, Ali TA, Fadda AA, J. Surfactants Deterg., 19, 119 (2015)
Cornellas A, Perez L, Comelles F, Ribosa I, Manresa A, Garcia MT, J. Colloid Interface Sci., 355(1), 164 (2011)
Kuperkar K, Modi J, Patel K, J. Surfactants Deterg., 15, 107 (2011)
McDonnell G, Russell AD, Clin. Microbiol. Rev., 12, 147 (1999)
Harkes G, Van der Mei H, Rouxhet P, Dankert J, Busscher H, Feijen J, Cell. Biochem. Biophys., 20, 17 (1992)
Vaara M, Microbiol. Rev., 56, 395 (1992)
Diz M, Manresa A, Pinazo A, Erra P, Infante M, J. Chem. Soc.-Perkin Trans., 2, 1871 (1994)
