Synthesis and properties of quaternary ammonium surfactants containing a methoxy benzyl substitute

Zhao, Zhenlong; Guo, Xiangfeng; Jia, Lei; Liu, Yanyan

doi:10.1039/c4ra07363k

Cited by 18 publications

(6 citation statements)

References 40 publications

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“…Benzalkonium chloride ( BAC‐12 ) is a typical cationic surfactant found in bactericidal agents (Ford et al, ). The surface activity and antimicrobial activity of BAC‐12 were enhanced by introducing an m‐methoxy group (Zhao et al, ). However, the influence of inserting an amide bond into the molecular structure on the performance of BAC‐12 was not reported.…”

Section: Introductionmentioning

confidence: 99%

The Effects of Amide Bonds and Aromatic Rings on the Surface Properties and Antimicrobial Activity of Cationic Surfactants

Wang

et al. 2018

J Surfact & Detergents

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The cationic surfactants containing aromatic rings and amide bonds, N,N-dimethyl-N-dodecyl-2-pyrimidinylcarbamoylmethyl ammonium chloride (a), N,N-dimethyl-N-dodecyl-2-thiazolylcarbamoylmethyl ammonium chloride (b), and N,N-dimethyl-N-dodecylphenylcarbamoylmethyl ammonium chloride (c), were synthesized and characterized. The surface tension and conductivity values were employed to investigate the absorption and micellization behavior of the three cationic surfactants. The results showed that the synthesized surfactants have shown a low critical micelle concentration (CMC) and a high adsorption efficiency (pC 20 ) compared with the traditional cationic surfactant of N,N-dimethyl-Ndodecyl-N-benzyl ammonium chloride (BAC-12). The aromatic rings of the a, b, and c molecular structures were analyzed using the 1 H NMR spectra for electrostatic repulsion effects between hydrophilic headgroups. The size distribution of the micelles was derived using dynamic light scattering (DLS) techniques. In addition, the foaming ability of a, b, c, and BAC-12 was investigated and the antimicrobial activity of a, b, c, and BAC-12 against Escherichia coli, Staphylococcus aureus, and Bacillus subtilis was examined. The effects of amide bonds and aromatic rings on the surface properties and antimicrobial activity of a, b, and c were analyzed and compared with BAC-12 of the same alkyl chain length. The synthesized surfactants exhibited a high surface ability and better antibacterial activity compared with BAC-12.

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Section: Introductionmentioning

confidence: 99%

The Effects of Amide Bonds and Aromatic Rings on the Surface Properties and Antimicrobial Activity of Cationic Surfactants

Wang

et al. 2018

J Surfact & Detergents

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“…The reduction resulted in an O-to N-acyl migration to yield a monoamide ( Figure 9). Chiral C4 compounds are synthetic units useful for the production of various pharmaceuticals and chiral polymers [116]. As an example, S-CHBN is used as a precursor of atorvastatin, a cholesterol-lowering drug [114].…”

Section: Synthesis Of Mononoamide Derivativesmentioning

confidence: 99%

“…Gemini compounds have high surface activity and low critical micelle concentration (CMC). These properties enhance their water-solubility and confer a better viscosity than single-chain surfactants at equal molar mass concentration [116,[225][226][227][228][229][230][231]. Consequently, their efficiency is improved [232], allowing them to be used in smaller quantities compared to conventional surfactants [232].…”

Section: Synthesis Of Ionic Compounds Based On Quaternary Bis-ammoniumentioning

confidence: 99%

Preparation and Uses of Chlorinated Glycerol Derivatives

et al. 2020

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Crude glycerol (C3H8O3) is a major by-product of biodiesel production from vegetable oils and animal fats. The increased biodiesel production in the last two decades has forced glycerol production up and prices down. However, crude glycerol from biodiesel production is not of adequate purity for industrial uses, including food, cosmetics and pharmaceuticals. The purification process of crude glycerol to reach the quality standards required by industry is expensive and dificult. Novel uses for crude glycerol can reduce the price of biodiesel and make it an economical alternative to diesel. Moreover, novel uses may improve environmental impact, since crude glycerol disposal is expensive and dificult. Glycerol is a versatile molecule with many potential applications in fermentation processes and synthetic chemistry. It serves as a glucose substitute in microbial growth media and as a precursor in the synthesis of a number of commercial intermediates or fine chemicals. Chlorinated derivatives of glycerol are an important class of such chemicals. The main focus of this review is the conversion of glycerol to chlorinated derivatives, such as epichlorohydrin and chlorohydrins, and their further use in the synthesis of additional downstream products. Downstream products include non-cyclic compounds with allyl, nitrile, azide and other functional groups, as well as oxazolidinones and triazoles, which are cyclic compounds derived from ephichlorohydrin and chlorohydrins. The polymers and ionic liquids, which use glycerol as an initial building block, are highlighted, as well.

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“…Cationic surfactants are widely applied in germicides, [1][2][3] emul-sication, 4 foaming, 5 detergent, 6 drug delivery 7,8 and materials synthesis, 9,10 et al Recently, quaternary ammonium surfactants containing amide, ether, or other functional groups have been extensively studied due to several interesting properties such as low-toxicity or biodegradability. [11][12][13] It was found that the surfactants with amide functionalization could enhance the aggregation ability compared with those without an amide group, and the aggregation properties depend strongly on the position and number of amide bonds.…”

Section: Introductionmentioning

confidence: 99%

Aggregation behaviours and bactericidal activities of novel cationic surfactants functionalized with amides and ether groups

et al. 2015

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Synthesis and properties of quaternary ammonium surfactants containing a methoxy benzyl substitute

Abstract: m-MDRA-n exhibit high surface activity, excellent adsorptive and bacterial properties, thermodynamic functions of micellization for m-MDRA-n were researched.

Cited by 18 publications

References 40 publications

The Effects of Amide Bonds and Aromatic Rings on the Surface Properties and Antimicrobial Activity of Cationic Surfactants

The Effects of Amide Bonds and Aromatic Rings on the Surface Properties and Antimicrobial Activity of Cationic Surfactants

Preparation and Uses of Chlorinated Glycerol Derivatives

Aggregation behaviours and bactericidal activities of novel cationic surfactants functionalized with amides and ether groups

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