Synthesis and properties of stellate lactosamide quaternary ammonium surfactants

Liu, Zhi; Shi, Xiufang; Zhang, Erzhuang; Pan, Yi‐Lun; Li, Xiaoming; Wang, Hui; Liu, Wen

doi:10.1016/j.colsurfa.2021.127317

Cited by 13 publications

(14 citation statements)

References 34 publications

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“…The TEM images displayed in Figure 9 show that all the C n DDGPB surfactants formed spherical micelles in aqueous solution at a concentration of 5.0 mmol/L. As can be seen from Figure 10 , as the concentration of the C n DDGPB surfactant increased, the aggregate size first increased, then decreased, and then increased again, as was previously observed for the stellate lactose amide quaternary ammonium surfactants (C n DBLB) [ 35 ].…”

Section: Resultssupporting

confidence: 69%

Synthesis and Performance of Double-Chain Quaternary Ammonium Salt Glucosamide Surfactants

et al. 2022

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A series of double-chain quaternary ammonium salt surfactants N-[N′[3-(gluconamide)] propyl-N′-alkyl]propyl-N, N-dimethyl-N-alkyl ammonium bromide (CnDDGPB, where n represents a hydrocarbon chain length of 8, 10, 12, 14 and 16) were successfully synthesized from D (+)-glucose δ-lactone, N, N-dimethyldipropylenetriamine, and bromoalkane using a two-step method consisting of a proamine-ester reaction and postquaternization. Their surface activity, adsorption, and aggregation behavior in aqueous solution were investigated via measurements of dynamic/static surface tension, contact angle, dynamic light scattering, and transmission electron microscopy. An analysis of their application performance in terms of wettability, emulsifying properties, toxicity, and antibacterial properties was conducted. The results show that with increasing the carbon chain length of the CnDDGPB surfactants, their critical micelle concentration (CMC) increased and the pC20 and efficiency in the interface adsorption of the target product gradually decreased. Moreover, the influence of the hydrophobic carbon chain length on the surface of polytetrafluoroethylene (PTFE) was even greater for the wetting effect, reducing the contact angle to 32° within the length range of C8–C14. The results of the contact angle change and the wettability experiments proved that C10DDGPB exhibited the best wettability. The liquid paraffin and soybean oil emulsification ability of CnDDGPB showed an upward trend followed by a downward trend with the growth of the carbon chain, with C12DDGPB exhibiting the best emulsification performance. The Dlong/Dshort ratio was far lower than 1, which indicates mixed-kinetic adsorption. The surfactants formed spherical micelles and showed a unique aggregation behavior in aqueous solution, which showed an increase–decrease–increase trend with the change in concentration. A cell toxicity and acute oral toxicity experiment showed that the CnDDGPB surfactants were less toxic than the commonly used surfactant dodecyldimethylbenzyl ammonium chloride (1227). In addition, at a concentration of 150 ppm, CnDDGPB exhibited the same bacteriostatic effect as 1227 at a concentration of 100 ppm. The results demonstrate that sugar-based amide cationic surfactants are promising as environmentally friendly disinfection products.

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Section: Resultssupporting

confidence: 69%

Synthesis and Performance of Double-Chain Quaternary Ammonium Salt Glucosamide Surfactants

et al. 2022

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“…Synthesis and Characterization. These synthesized amide quaternary ammonium surfactants were characterized by their MS, 1 H NMR, 13 C NMR, and FTIR spectra. For the details of these spectral characterizations, see the Supporting Information.…”

Section: Resultsmentioning

confidence: 99%

“…The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acsomega.2c06353. Details of the spectral characterizations of compounds a−d; MS, 1 H NMR, 13 C NMR, and FTIR spectra of compounds a−d; plots of conductivity (κ) against temperature; explanation of eqs 1 and 2; fluorescence spectra; polydispersity parameters; plots of foam height against time (PDF)…”

Section: * Sı Supporting Informationmentioning

confidence: 99%

“…Mass spectrometry (MS) analysis was performed using an AB SCIEX API3200 liquid chromatography tandem mass spectrometer. 1 H NMR and 13 C NMR spectra were obtained on a Bruker AVANCEIII HD proton nuclear magnetic resonance spectrometer with CD 3 OD and DMSO-d 6 as solvents. Fourier transform infrared (FTIR) spectra were recorded on a Nicolet is 10 infrared spectrometer.…”

Section: Synthesis Of Alkyl Amidementioning

confidence: 99%

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Green Synthesis, Surface Activity, Micellar Aggregation, and Foam Properties of Amide Quaternary Ammonium Surfactants

Jia

Wei

et al. 2022

ACS Omega

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A series of amide quaternary ammonium surfactants with the formula 9,11,13,15) were synthesized using a fatty acid, N,Ndimethylethylenediamine, and a green reagent dimethyl carbonate. A comparative study of the four surfactants in terms of surface activity, aggregation characteristics, and foam properties was conducted. The results show that these amide quaternary ammonium surfactants reduce the surface tension of water to a minimum value of 23.69 mN•m −1 at a concentration of 1.55 × 10 −4 mol•L −1 and self-assemble spontaneously into aggregates, which are mostly vesicles. Furthermore, with increasing the alkyl chain length, their critical micelle concentration (CMC) values and surface tension values at the CMC (γ CMC ) decrease and then increase, and the degree of counterion binding (β) decreases. It is also found that these amide quaternary ammonium surfactants exhibit excellent foam ability and foam stability.

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Adsorption and aggregation behavior of Gemini surfactants with organic counterions

et al. 2023

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Synthesis and properties of stellate lactosamide quaternary ammonium surfactants

Cited by 13 publications

References 34 publications

Synthesis and Performance of Double-Chain Quaternary Ammonium Salt Glucosamide Surfactants

Synthesis and Performance of Double-Chain Quaternary Ammonium Salt Glucosamide Surfactants

Green Synthesis, Surface Activity, Micellar Aggregation, and Foam Properties of Amide Quaternary Ammonium Surfactants

Adsorption and aggregation behavior of Gemini surfactants with organic counterions

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