Surface, thermodynamic and biological activities of some synthesized Gemini quaternary ammonium salts based on polyethylene glycol

Tawfik, Salah M.; Abd-Elaal, Ali A.; Shaban, Samy M.; Roshdy, A.A.

doi:10.1016/j.jiec.2015.05.011

Cited by 57 publications

(31 citation statements)

References 30 publications

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“…As suggested by the structural descriptors predicting antiseptic efficacy summarized in Cronin et al’s () work, hydrogen bonds help to strengthen the interaction between antibacterial compounds and the outer cell membrane, further contributing to enhanced antibacterial efficacy. QAC with polyethylene glycol chains synthesized by Abd‐Elaal and colleagues exhibited improved antibacterial efficacy owing to the presence of strong hydrogen‐bond interaction (Tawfik et al, ), in accordance with the finding of our work.…”

Section: Resultssupporting

confidence: 92%

“…In the field of antimicrobial agents, QAC with various structures have been developed and thoroughly investigated (Aiad, Tawfik, El-Shafie, & Rhman, 2017;Massi, Guittard, Géribaldi, Levy, & Duccini, 2003;Massi, Guittard, Levy, & Geribaldi, 2009;Negm, Aiad, & Tawfik, 2010;Tawfik, Abd-Elaal, Shaban, & Roshdy, 2015). However, besides the positively charged nitrogen atom, other cation-containing antiseptics remain comparatively obscure.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Surface Activity, and Antimicrobial Efficacy of Diaryliodonium Salt‐Derived Amphiphiles

Huang

et al. 2018

J Surfact & Detergents

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Two sets of 19 amphiphiles derived from diaryliodonium salt in the form of 4‐methylbenzenesulfonate salts and trifluoromethanesulfonate salts were synthesized in good yields through the oxidation of 17 different aryl iodides using oxone (potassium peroxymonosulfate) as the oxidation agent in Route I and meta‐chloroperoxybenzoic acid as the oxidation agent in Routes II and III, followed by Friedel–Crafts reaction with (2‐(2‐(2‐methoxyethoxy)ethoxy)ethoxy)benzene to obtain the target compounds (1–19). Their structures were characterized by 1H nuclear magnetic resonance (NMR), 13C NMR, and high‐resolution mass spectrometry studies. Their surface activities were evaluated on the basis of surface tension and critical micelle concentration measurements by the Wilhelmy plate method at 25 °C. With their good water solubility, diaryliodonium salts (1–19) have excellent short‐term bactericidal efficacy against Bacillus cereus in the concentration of 600 ppm at 20 °C. After compounding 1 or 18 with the broad‐spectrum but skin‐irritating antibacterial agent Kathon CG (methylchloroisothiazolinone in combination with methylisothiazolinone) in the ratio of 1:1 by mass, both formulations maintained lethality rate of >90% after 48 h.

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Section: Resultssupporting

confidence: 92%

Section: Introductionmentioning

confidence: 99%

Synthesis, Surface Activity, and Antimicrobial Efficacy of Diaryliodonium Salt‐Derived Amphiphiles

Huang

et al. 2018

J Surfact & Detergents

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“…Notably, these γ CAC values were significantly lower than those of hydrocarbon-based surfactants (30-40 mN/m) [31] and were similar to those reported for other trisiloxane surfactants (20-25 mN/m) [7,8] and fluorosurfactants (18-28 mN/m) [9], which might be attributed to the two hydrophobic trisiloxane groups of the gemini surfactant molecules better facilitating the self assembly into aggregates and more efficiently decreasing the surface tension than the corresponding monomeric surfactants. Moreover, other physicochemical parameters (Γ CAC , A CAC , △G θ mic , and △G θ ads ) related to surface activity were calculated according to previous studies [32][33][34][35]. The variables Г max and A CAC are also related to m and n, and an increase in the spacer group (CH 2 ) resulted in a slight decrease in Г max and an increase in A CAC .…”

Section: Surface Activities and Aggregation Properties Of Surfactantsmentioning

confidence: 99%

A gemini-type superspreader: Synthesis, spreading behavior and superspreading mechanism

Lin

Wang

Bai

et al. 2017

Chemical Engineering Journal

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Please cite this article as: A gemini-type superspreader: synthesis, spreading behavior and superspreading mechanism, Chemical Engineering Journal (2016), doi: http://dx.doi.org/10. 1016/j.cej.2016.12.132 This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. ABSTRACTThis paper describes the facile microwave-assisted synthesis of a series of trisiloxane gemini superspreaders, as well as their surface and aggregation properties and superspreading behavior on plant leaf surfaces. The molecular structures of the trisiloxane gemini surfactants were characterized by Fourier transform infrared spectroscopy (FTIR) and 1 H nuclear magnetic resonance spectroscopy ( 1 H NMR). The obtained thermodynamic parameters showed that an increase in the spacer group (CH 2 ) resulted in decreases in the critical aggregation concentration (CAC), corresponding surface tension (γ CAC ), and surface excess concentration (Γ max ) but increases in the occupied area per surfactant molecule (A CAC ) and absolute values of the standard free energies of aggregation (△G θ mic ) and adsorption (△G θ ads ). An increase in ethoxy units (CH 2 -CH 2 -O-) resulted in increases in the CAC, γ CAC , and A CAC but decreases in Г max and the absolute values of △G θ mic and △G θ ads . The transmission electron microscopy and dynamic light scattering results showed that the average sizes of the aggregates of superspreader solutions increased with an increasing number of spacer units (CH 2 ) but decreased with an increasing number of ethoxy units (CH 2 -CH 2 -O-). The dynamic spreading behavior results demonstrated that the average spreading velocity increased with increasing spacer chain length, and the dependence of the maximum spreading velocity on the ethoxy chain length was nonmonotonous with a maximum at n(EO) = 8.68. The optimal HLB value was essential to obtaining good superspreading behavior, and the substrate wettability (hydrophobic rice plant and hydrophilic mango plant surfaces) greatly influenced the superspreading. The synergistic effects from the precursor film and Marangoni effect existed in the proposed superspreading model.

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“…Measurements of foam power were done after shaking 100 mL of 0.1% concentration of the synthesized cationic surfactant solution vigorously in a closed, graduated, 250-mL cylinder at 30°C. Foam formation was measured by the foam height (in ml) initially produced, and foam stability was recorded by the time [28]. The biodegradability was measured according to the previous work [29].…”

Section: Foaming Power and Biodegradabilitymentioning

confidence: 99%

Novel Quaternary Ammonium‐Based Cationic Surfactants: Synthesis, Surface Activity and Evaluation as Corrosion Inhibitors for C1018 Carbon Steel in Acidic Chloride Solution

El‐Lateef

Tantawy

Abdelhamid

2017

J Surfact & Detergents

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A novel class of quaternary ammonium-based cationic surfactants is synthesized and characterized via spectroscopic methods (FTIR, 1 H NMR and 13 C NMR). The surface properties, foaming power and biodegradability of the synthesized cationic surfactants are determined using the surface tension technique. The protection performance with their adsorption mechanisms for carbon steel is evaluated in a 15% HCl solution by a series of techniques including electrochemical impedance spectroscopy, potentiodynamic polarization curves, scanning electron microscopy (SEM), X-ray spectroscopy, and UV-visible spectroscopy. The surfactants are found to be excellent corrosion inhibitors for carbon steel. The results show that the inhibition efficiencies are increased by increasing the concentration and the hydrophobic chain length of the tested compounds reaching the maximum at 250 ppm. The potentiodynamic polarization curves suggested that the inhibitors behave as a mixed type with predominant cathodic inhibition and the corrosion behavior can be explained by the adsorption film mechanism. Moreover, the mode of adsorption obeys the Langmuir adsorption isotherm; also, the adsorbed layer on the surface of the metal is approved by using SEM. . As a researcher, he is currently interested in synthesis of organic compounds and their applications. J Surfact Deterg (2017) 20:735-753 753

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Surface, thermodynamic and biological activities of some synthesized Gemini quaternary ammonium salts based on polyethylene glycol

Cited by 57 publications

References 30 publications

Synthesis, Surface Activity, and Antimicrobial Efficacy of Diaryliodonium Salt‐Derived Amphiphiles

Synthesis, Surface Activity, and Antimicrobial Efficacy of Diaryliodonium Salt‐Derived Amphiphiles

A gemini-type superspreader: Synthesis, spreading behavior and superspreading mechanism

Novel Quaternary Ammonium‐Based Cationic Surfactants: Synthesis, Surface Activity and Evaluation as Corrosion Inhibitors for C1018 Carbon Steel in Acidic Chloride Solution

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