Synthesis, Surface and Antimicrobial Properties of Fatty Morpholide and Piperidide Derivatives

Abstract

Unsaturated fatty N-acyl morpholide and piperidide derivatives were prepared by the reaction of the acid chloride of oleic and linoleic acids as well as the mixed fatty acid chlorides of olive, linseed and castor oils with morpholine and piperidine. The sodium bisulfite and mercapto acetic acid were added to the prepared unsaturated fatty amides to give sulfonated and methylthiocarboxylate morpholide and piperidide derivatives.These derivatives were characterized using infrared (IR), 1 H nuclear magnetic resonance (NMR) and mass spectroscopy (MS), they showed excellent lowering power of surface tension, foaming stability and emulsifying property. On the other hand, these derivatives showed a broad antimicrobial spectra as high as chloramphenicol against all the tested microorganisms. It was found that compounds containing a carboxylate hydrophilic group were less efficient than those with a suflonate group with respect to foaming power, foam stability, emulsification and antimicrobial effect.

Synthesis, Antimicrobial Activity and Micellization of Gemini Anionic Surfactants in a Pure State as Well as Mixed With a Conventional Nonionic Surfactant

“…The The CMC values in Tables 2, 3 and 4 reveal that the NI product has a higher CMC value than that of surfactants GA 12 , GA 16 and GA 18 . This result may be due the solubility of NI being completely controlled by solvation, whereas the solubility occurs by an ionization-solvation mixed process with GA 12 , GA 16 and GA 18 .…”

“…This result may be due the solubility of NI being completely controlled by solvation, whereas the solubility occurs by an ionization-solvation mixed process with GA 12 , GA 16 and GA 18 . These results were observed in an earlier study [17,18] and were attributed to the stronger repulsive electrostatic nature of the polar group in an gemini anionic, with respect to the static hydration requirement of the O-CH 2 CH 2 -O group in NI.…”

“…Pure nonionic (y 1 ) 3. The micellar mole fraction of gemini anionic surfactant moieties GA 12 , GA 16 and GA 18 in a mixed surfactant solution may be expressed by the following equation suggested by Rubingh [7]:…”

“…The surfactants GA 12 , GA 16 and GA 18 in this study were assayed against different microbes. The organisms used in the assay were Gram-positive bacteria such as S. aureus (ATCC 25923) and S. pyogenes (ATCC 19615), and Gramnegative bacteria such as P. phaseolicola (GSPB 2828) and P. fluorescens (597).…”

“…Variation of surface tension vs. log C of single GA 12 , single NI product and the mixed GA 12 with NI at different mole Variation of surface tension vs. log C of single GA 16 , single NI product and the mixed GA16 with NI at different mole…”