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Synthesis and evaluation of micellar properties and antimicrobial activities of imidazole‐based surfactants
Author(s) -
Kanjilal Sanjit,
Sunitha Sadula,
Reddy Paidimarla S.,
Kumar Koochana P.,
Murty Upadyayula S. N.,
Prasad Rachapudi B. N.
Publication year - 2009
Publication title -
european journal of lipid science and technology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.614
H-Index - 94
eISSN - 1438-9312
pISSN - 1438-7697
DOI - 10.1002/ejlt.200800292
Subject(s) - imidazole , cationic polymerization , chemistry , alkyl , pulmonary surfactant , amide , micelle , critical micelle concentration , organic chemistry , antimicrobial , micellar solutions , homologous series , polymer chemistry , aqueous solution , biochemistry
The synthesis of two types of imidazole‐based surfactants, [(ROCOCH 2 MIm)Br] and [(RNHCOCH 2 MIm)Br], of varying chain lengths (C 10 , C 12 and C 16 ), was conducted in the present work. The synthesis involves an initial reaction of bromoacetic acid with fatty alcohols or fatty amines, followed by quaternization with N ‐methyl imidazole. The micellar properties of all the synthesized compounds were determined using surface tensiometry and compared with [(RMIm)Br], a well‐studied alkyl‐substituted imidazole‐based surfactant. Within the same homologous series, a decrease in critical micelle concentration (cmc) was observed with increasing alkyl chain length in all three types of cationic surfactants. Introduction of an ester [(ROCOCH 2 MIm)Br] or an amide group [(RNHCOCH 2 MIm)Br] in the alkyl chain lowers the cmc when compared to a cationic surfactant without functional group, [(RMIm)Br]. The synthesized surfactants were also assayed for antimicrobial activities and found to possess good activities against selected strains.