Synthesis and evaluation of new imidazolium‐based aromatic ether functionalized cationic mono and gemini surfactants

作者: Sadula Sunitha , Paidimarla S. Reddy , Rachapudi B. N. Prasad , Sanjit Kanjilal

DOI: 10.1002/EJLT.201000437

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摘要: Synthesis of a novel series imidazolium-based surfactants, [(ROArCH 2 MIm)Br] with aromatic ether functionalized hydrophobic tail varying chain lengths and also their gemini counterparts were conducted in the present work. involves initial conversion 4-hydroxy benzoic acid to its methyl ester followed by O-alkylation long fatty alcohols, which was subsequently reduced brominated get 4-alkyloxy benzyl bromide. For synthesis monocationic surfactant, bromide is quaternized N-methylimidazole. Gemini surfactants are synthesized coupling imidazole quaternization dibromoalkane. The surface properties all determined using tensiometry. Within same homologous series, expected decrease critical micelle concentration (cmc) increase hydrophobicity observed for shorter homologs. However, deviation cmc value from regularity when number carbon atoms exceeded certain number. values geminis found be remarkably low compared monomeric counterparts.

参考文章(21)
A. Modaressi, H. Sifaoui, M. Mielcarz, U. Domańska, M. Rogalski, Influence of the molecular structure on the aggregation of imidazolium ionic liquids in aqueous solutions Colloids and Surfaces A: Physicochemical and Engineering Aspects. ,vol. 302, pp. 181- 185 ,(2007) , 10.1016/J.COLSURFA.2007.02.020
Limei Zhou, Xiaohui Jiang, Yintao Li, Zhi Chen, Xingqi Hu, Synthesis and properties of a novel class of gemini pyridinium surfactants. Langmuir. ,vol. 23, pp. 11404- 11408 ,(2007) , 10.1021/LA701154W
Caroline McGregor, Christele Perrin, Myrna Monck, Patrick Camilleri, Anthony J. Kirby, Rational approaches to the design of cationic gemini surfactants for gene delivery. Journal of the American Chemical Society. ,vol. 123, pp. 6215- 6220 ,(2001) , 10.1021/JA005681C
Pasupati Mukerjee, The nature of the association equilibria and hydrophobic bonding in aqueous solutions of association colloids Advances in Colloid and Interface Science. ,vol. 1, pp. 242- 275 ,(1967) , 10.1016/0001-8686(67)80005-8
André Laschewsky, Laurent Wattebled, Michel Arotçaréna, Jean-Louis Habib-Jiwan, Rivo H. Rakotoaly, Synthesis and Properties of Cationic Oligomeric Surfactants Langmuir. ,vol. 21, pp. 7170- 7179 ,(2005) , 10.1021/LA050952O
S. Khabnadideh, Z. Rezaei, A. Khalafi-Nezhad, R. Bahrinajafi, R. Mohamadi, A.A. Farrokhroz, Synthesis of N-alkylated derivatives of imidazole as antibacterial agents. Bioorganic & Medicinal Chemistry Letters. ,vol. 13, pp. 2863- 2865 ,(2003) , 10.1016/S0960-894X(03)00591-2
Mariano J. L. Castro, José Kovensky, Alicia Fernández Cirelli, New Family of Nonionic Gemini Surfactants. Determination and Analysis of Interfacial Properties Langmuir. ,vol. 18, pp. 2477- 2482 ,(2002) , 10.1021/LA001549E
Omar A. El Seoud, Paulo Augusto R. Pires, Thanaa Abdel-Moghny, Erick L. Bastos, Synthesis and micellar properties of surface-active ionic liquids: 1-Alkyl-3-methylimidazolium chlorides Journal of Colloid and Interface Science. ,vol. 313, pp. 296- 304 ,(2007) , 10.1016/J.JCIS.2007.04.028