Benzene ring containing cationic gemini surfactants: Synthesis, surface properties and antibacterial activity

Taleb, Khadidja; Mohamed-Benkada, Mustapha; Benhamed, Nadjia; Saïdi-Besbes, Salima; Grohens, Yves; Derdour, Aïcha

doi:10.1016/j.molliq.2017.06.008

Cited by 89 publications

(42 citation statements)

References 50 publications

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“…The negative values of

normalΔ G_{m}^{o}

and

normalΔ H_{m}^{o}

at different temperatures indicate that micellization is spontaneous and exothermic (Taleb et al, ; Zhao et al, ). It was noticed in Table that

normalΔ G_{m}^{o}

were closely related to the alkyl carbon number, where the C 16 member has the smallest values.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Properties of Novel Phenylenediamine Gemini Surfactants

Wang

Lin

et al. 2019

J Surfact & Detergents

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In the present work, a two‐step method was adopted to synthesize a series of novel Gemini surfactants using N,N‐dimethylalkyl amines (alkyl length = C12, C16 and C18), epichlorohydrin, and n‐phenyllenediamine as starting materials. The products were characterized using mass spectroscopy (MS) and nuclear magnetic resonance spectroscopy (1H NMR). Systematic experiments were conducted to evaluate their surface activity, foaming properties, and antibacterial performance. Results showed the critical micelle concentrations (CMC) of the C12‐based, C16‐based, and C18‐based phenylenediamine surfactants were 3.295 × 10−3, 2.532 × 10−4, and 3.140 × 10−4 mol L−1 at 298 K, respectively, with corresponding surface tension (γcmc) values of 28.24, 31.95, and 35.06 mN m−1 under the same conditions. The Gemini surfactants showed not only good surface activity and foaming properties, but also demonstrated good antimicrobial performance against Gram‐positive and Gram‐negative bacteria and fungi.

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“…The negative values of

normalΔ G_{m}^{o}

and

normalΔ H_{m}^{o}

at different temperatures indicate that micellization is spontaneous and exothermic (Taleb et al, ; Zhao et al, ). It was noticed in Table that

normalΔ G_{m}^{o}

were closely related to the alkyl carbon number, where the C 16 member has the smallest values.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Properties of Novel Phenylenediamine Gemini Surfactants

Wang

Lin

et al. 2019

J Surfact & Detergents

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“…The cmc dataset of gemini cationic surfactant were collected from multiple publications 20,21,22,23,24,25 . This dataset containing 231 compounds of gemini cationic surfactants including with their cmc value.…”

Section: Experimental Materials and Methods Data Preparationmentioning

confidence: 99%

QSPR Models for Predicting Critical Micelle Concentration of Gemini Cationic Surfactants Combining Machine-Learning Methods and Molecular Descriptors

Setiawan¹,

Mudasir²,

Wijaya³

2020

Preprint

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A data set of 231 diverse gemini cationic surfactants has been developed to correlate the logarithm of critical micelle concentration (cmc) with the molecular structure using a quantitative structure-property relationship (QSPR) methods. The QSPR models were developed using the Online CHEmical Modeling environment (OCHEM). It provides several machine learning methods and molecular descriptors sets as a tool to build QSPR models. Molecular descriptors were calculated by eight different software packages including Dragon v6, OEstate and ALogPS, CDK, ISIDA Fragment, Chemaxon, Inductive Descriptor, SIRMS, and PyDescriptor. A total of 64 QSPR models were generated, and one consensus model developed by using a simple average of 13 top-ranked individual models. Based on the statistical coefficient of QSPR models, a consensus model was the best QSPR models. The model provided the highest R 2 = 0.95, q 2 = 0.95, RMSE = 0.16 and MAE = 0.11 for training set, and R 2 = 0.87, q 2 = 0.87, RMSE = 0.35 and MAE = 0.21 for test set. The model was freely available at https://ochem.eu/model/8425670 and can be used for estimation of cmc of new gemini cationic surfactants compound at the early steps of gemini cationic surfactants development.

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“…Increasing hydrocarbon chain length destroys the water structure; consequently, the aqueous system free energy increases. Basically this is sufficient to force the FHPAO, FHPAD, and FHPAH unimers to migrate to the aqueous phase interface and/or aggregate in clusters to decrease that unfavorable increase in the solution free energy (El-Sukkary et al, 2010;Taleb et al, 2017;Xu et al, 2017). In addition, by raising the solution temperature, the hydration around the FHPAO, FHPAD, and FHPAH hydrophilic head decreased, which led to an increase in system free energy, promoting unimer migration to the solution interface and/or aggregation in micelles (Badr et al, 2020;Bao et al, 2017;.…”

Section: Surfactant Behavior: Thermodynamic Viewmentioning

confidence: 99%

Novel Gemini Cationic Surfactants: Thermodynamic, Antimicrobial Susceptibility, and Corrosion Inhibition Behavior against Acidithiobacillus ferrooxidans

Labena

Hamed

Ismael

et al. 2020

J Surfact & Detergents

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The Egyptian oil and gas industry is suffering from severe metal corrosion problems, particularly microbial‐induced corrosion. There is limited knowledge on the corrosion inhibition of carbon steels in the presence of an acidophilic, iron‐oxidizing bacterial species Acidithiobacillus ferrooxidans. Therefore, in this study, novel Gemini cationic surfactants, in three forms depending on variation in alkyl chains of 8, 12, and 16 carbon atoms named FHPAO, FHPAD, and FHPAH, respectively, were synthesized and characterized by Fourier transform infrared and nuclear magnetic resonance spectroscopy. The surface parameters and the thermodynamic of the synthesized surfactants were evaluated at three different temperatures, 20, 40, and 60 °C. The synthesized Gemini cationic surfactants were tested as broad‐spectrum antimicrobial, antibacterial and anticandida agents. They evaluated as biocides and corrosion inhibitors against Acidithiobacillus ferrooxidans. FHPAD showed higher adsorption ability at the solution interface and higher affinity to construct micelles than FHPAO and FHPAH. Both adsorption and micellization processes were hydrophobic and temperature dependent. FHPAO, FHPAD and FHPAH exhibited wide‐spectrum antimicrobial activities, and the highest activity and the lowest minimum bactericidal/fungicidal inhibitory concentrations were attributed to FHPAD. Furthermore, synthesized FHPAD demonstrated the highest metal corrosion inhibition efficiency of 95.5% at 5 mM in comparison to 87.5% and 81.7% for FHPAO and FHPAH, respectively. In conclusion, this study provides novel synthesized cationic surfactants with many applications in the oil and gas industry, such as broad‐spectrum antimicrobial, biocides, and corrosion inhibitors for acidophilic, iron‐oxidizing bacterial species Acidithiobacillus ferrooxidans.

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Benzene ring containing cationic gemini surfactants: Synthesis, surface properties and antibacterial activity

Cited by 89 publications

References 50 publications

Synthesis and Properties of Novel Phenylenediamine Gemini Surfactants

Synthesis and Properties of Novel Phenylenediamine Gemini Surfactants

QSPR Models for Predicting Critical Micelle Concentration of Gemini Cationic Surfactants Combining Machine-Learning Methods and Molecular Descriptors

Novel Gemini Cationic Surfactants: Thermodynamic, Antimicrobial Susceptibility, and Corrosion Inhibition Behavior against Acidithiobacillus ferrooxidans

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