Gemini Surfactants Research Articles

Ct-DNA compaction by nanoparticles formed by silica and gemini surfactants having hydroxyl group substituted spacers: In vitro, in vivo, and ex vivo gene uptake to cancer cells

ct-DNA compaction by nanoparticles formed by silica and gemini surfactants having hydroxyl group substituted spacers: In vitro, in vivo, and ex vivo gene uptake to cancer cells

Synthesis and surfactant properties of sulfonate Gemini surfactants

Abstract In this study, a novel high salinity resistant, high temperature tolerant sulfonate Gemini surfactant (CK-3) for enhanced oil recovery was synthesized and is described. The critical micelle concentration (CMC) of CK-3 is 7.3 × 10−5 mol L−1 with a surface tension at CMC, γ CMC , of 30.88 mN m−1, and a pC20 value of 4.80. Moreover, increasing temperature led to delayed micellization, indicating the superior surface activity inherent in Gemini surfactants. When CK-3 was evaluated as an imbibing agent, an interfacial tension of 8.3 × 10−2 mN m−1 was observed between a 0.3 wt% CK-3 solution and crude oil, facilitated by hydrophobic group interactions which allow crude oil detachment. Finally, CK-3 molecules exhibited stable adsorption on rock walls, influencing wetting reversal. Zeta potential measurements exceeding 30 mV indicated stability. In aged capillary tubes, a 0.3 wt% CK-3 solution exhibited a rise height of 2.9 cm. Imbibition experiments on natural core samples showed a water imbibition efficiency of 8.73 %, compared to a significantly improved efficiency of 50.78 % with a 0.3 wt% CK-3 solution. This study also demonstrated the imbibition process and mechanisms of the CK-3, providing novel insights for the efficient development of unconventional oil reservoirs and the enhancement of crude oil recovery rates.

Distinct Solubilization Mechanisms of Medroxyprogesterone in Gemini Surfactant Micelles: A Comparative Study with Progesterone

The solubilization behavior of medroxyprogesterone (MP) within gemini surfactant micelles (14-6-14,2Br−) was investigated and compared with that of progesterone to uncover distinct solubilization mechanisms. We employed 1H-NMR and 2D ROESY spectroscopy to elucidate the spatial positioning of MP within the micelle, revealing that MP integrates more deeply into the micellar core. This behavior is linked to the unique structural features of MP, particularly its 17β-acetyl group, which promotes enhanced interactions with the hydrophobic regions of the micelle, while the 6α-methyl group interacts with the hydrophilic regions of the micelle. The 2D ROESY correlations specifically highlighted interactions between the hydrophobic chains of the surfactant and two protons of MP, H22 and H19. Complementary machine learning and electron density analyses supported these spectroscopic findings, underscoring the pivotal role of the molecular characteristics of MP in its solubilization behavior. These insights into the solubilization dynamics of MP not only advance our understanding of hydrophobic compound incorporation in gemini surfactant micelles but also indicate the potential of 14-6-14,2Br− micelles for diverse drug delivery applications.

Liposomes in Anticancer Strategies

Chemotherapy drugs are not fully selective for cancer cells - they can also destroy healthy cells. Recent advances in nanotechnology have offered hope to overcome this problem. Liposome carriers are widely studied for their use to deliver drugs and genes inside cancer cells. Gemini quaternary ammonium salts (QAS) show great application potential among lipid carriers. Structures made of Gemini surfactants are characterized by a lower critical micelle concentration (CMC) and higher effectiveness in lowering the surface tension compared to monomeric forms of this type of compound. Encapsulation of a drug or genetic material is one of the critical steps in the formation of liposomal carriers. This efficient process allows one to minimize the number of necessary liposomes capable of delivering a certain amount of active substance. Delivery of a liposome to a solid tumor depends on the physiological factors of the tumor - vascularity, lymphatic drainage, interstitial fluid pressure – and on the physicochemical properties of the carrier. Many nanoparticles for targeted drug delivery have been tested in animal studies but have not achieved satisfactory clinical success. Promising preclinical research results are not always reflected in the treatment of patients. Therefore, understanding the relationships governing the transport of the drug and the carrier to the cancer cell seems to be a key challenge in modern nanotechnology.

Low-Foaming Nonionic Gemini Surfactants Containing Hydrophilic Poly(oxyethylene) Chain and Hydrophobic Di-tert-pentylbenzenes Groups.

Low-foaming nonionic gemini surfactants have a wide range of applications in industrial cleaning and photoresist development. In this study, three low-foaming nonionic gemini surfactants (S1, S2, and S3) with different poly(oxyethylene) chain lengths have been synthesized by using methoxy poly(ethylene glycol) and 2,5-di-tert-pentylhydroquinone. The chemical structures of the novel surfactants are confirmed by 1H NMR, Fourier transform infrared, and gel permeation chromatography (GPC), and their properties such as surface tension, wetting properties, emulsifying properties, and foaming properties are investigated. The surface tension values of S1, S2, and S3 at the critical micelle concentration are 40.29, 37.14, and 41.64 mN/m, exhibiting good surface activity. When the surfactant concentration is higher than 2 mM, the contact angles of S1 and S2 no longer change and can maintain 62 and 64°, showing good wetting properties. In addition, S3 can keep an emulsion state for 2 months at high concentrations, exhibiting good emulsion stability. Furthermore, all the prepared surfactants show good low-foaming properties. The initial foaming volumes of S1 are very low, less than 0.1 mL at various concentrations, less than 2% of the conventional surfactant sodium dodecyl sulfate. For S2, the initial foaming volumes at the concentration of 0.1, 1, 2, and 3 g/L are 1, 0.5, 0.55, and 0.45 mL, respectively. For S3, the initial foaming volumes show a general trend of increasing with concentration. The surfactants with longer poly(oxyethylene) chains possess more initial foaming volumes at the same concentration, which is because the greater cohesion between the surfactant molecules can increase the elasticity of the bubble film. Our study enriches the design rationales for low-foaming surfactants and motivates researchers to develop more advanced surfactants for industrial cleaning and photoresist development.

HYGIENIC PAPERS MODIFIED BY FUNCTIONAL BIOPOLYMER-BIOCIDE COMPOSITIONS IN A PILOT RESEARCH INSTALLATION

The aim of this work was to demonstrate the process of manufacturing and applying functionalising additives using a pilot research installation. As part of the optimisation evaluation, hygienic papers functionalised with biopolymer-biocide compositions based on chitosan, starch and Gemini surfactants were prepared. The microbiological properties and susceptibility to biodegradation of prototype hygienic papers (prepared in EPICOM) were assessed. In particular, the minimum amount of biopolymer and bioactive agent were determined to ensure the finished product exerted antibacterial activity against Staphylococcus aureus, Bacillus subtilis and Escherichia coli and was more than 90% biodegradable in a compost environment. Under optimal conditions, the hygienic paper exerted excellent antibacterial activity against S. aureus and E. coli as well as good activity against B. subtilis. Moreover, the hygienic paper showed more than 90% biodegradability in compost conditions within 8 weeks.

Micellar mediated preparation of cadmium sulfide (CdS) nanoparticles: Influence of cleavable spacer based cationic gemini surfactant

Cleavable spacer (s = diamido) based cationic gemini surfactant (with different alkyl tail lengths (m) abbreviated as g1; m = 12, g2; m = 14 or g3; m = 16), in aqueous micellar solution, was used to control the size and morphology of cadmium sulfide (CdS) nanoparticles (NPs), via modified chemical precipitation technique. The purity and stability of all CdS NPs were characterized by EDAX, FT-IR, TGA and zeta potential (ζ). By varying the geminis, significant size reduction (2–6 nm), enhanced capping capacity, and higher energy band gap (∼4.1 eV) have been found in CdS-g1 compared to other NPs, by using Dynamic Light Scattering (DLS), TEM, XRD and UV–visible spectroscopy. Photoluminescence (PL) spectra revealed an emission at 525 and 630 nm, showing the effect of geminis m concerning surface states of NP. Additionally, antioxidant and antimicrobial (on Gram-negative (E. coli and P. aeruginosa) and Gram-positive (S. aureus and B. subtilis) strains) activities of CdS NPs were examined by DPPH radical scavenging and agar plating-spot disc inoculation method, respectively. The results recommended a significant antioxidant activity in CdS-g1 with 45.6 %, while, selective antimicrobial activity was obtained on E. coli and S. aureus in all NP systems.

The Corrosion Inhibition Study of The Heat Exchanger Components in Chemical Cleaning Process Using the Synthesized new Cationic Gemini Surfactant

The Corrosion Inhibition Study of The Heat Exchanger Components in Chemical Cleaning Process Using the Synthesized new Cationic Gemini Surfactant

Synergistic effect of curcumin and tamoxifen loaded in pH-responsive gemini surfactant nanoparticles on breast cancer cells

BackgroundDrug combination therapy is preferred over monotherapy in clinical research to improve therapeutic effects. Developing a new nanodelivery system for cancer drugs can reduce side effects and provide several advantages, including matched pharmacokinetics and potential synergistic activity. This study aimed to examine and determine the efficiency of the gemini surfactants (GSs) as a pH-sensitive polymeric carrier and cell-penetrating agent in cancer cells to achieve dual drug delivery and synergistic effects of curcumin (Cur) combined with tamoxifen citrate (TMX) in the treatment of MCF-7 and MDA-MB-231 human BC cell lines.MethodsThe synthesized NPs were self-assembled using a modified nanoprecipitation method. The functional groups and crystalline form of the nanoformulation were examined by Fourier-transform infrared spectroscopy (FTIR), X-ray diffraction (XRD), differential scanning calorimetry (DSC), and dynamic light scattering (DLS) used to assess zeta potential and particle size, and the morphological analysis determined by transmission electron microscopy (TEM). The anticancer effect was evaluated through an in vitro cytotoxicity MTT assay, flow cytometry analysis, and apoptosis analysis performed for mechanism investigation.ResultsThe tailored NPs were developed with a size of 252.3 ± 24.6 nm and zeta potential of 18.2 ± 4.4 mV capable of crossing the membrane of cancer cells. The drug loading and release efficacy assessment showed that the loading of TMX and Cur were 93.84% ± 1.95% and 90.18% ± 0.56%, respectively. In addition, the drug release was more controlled and slower than the free state. Polymeric nanocarriers improved controlled drug release 72.19 ± 2.72% of Tmx and 55.50 ± 2.86% of Cur were released from the Tmx-Cur-Gs NPs after 72 h at pH = 5.5. This confirms the positive effect of polymeric nanocarriers on the controlled drug release mechanism. moreover, the toxicity test showed that combination-drug delivery was much more greater than single-drug delivery in MCF-7 and MDA-MB-231 cell lines. Cellular imaging showed excellent internalization of TMX-Cur-GS NPs in both MCF-7 and MDA-MB-231 cells and synergistic anticancer effects, with combination indices of 0.561 and 0.353, respectively.ConclusionThe combined drug delivery system had a greater toxic effect on cell lines than single-drug delivery. The synergistic effect of TMX and Cur with decreasing inhibitory concentrations could be a more promising system for BC-targeted therapy using GS NPs.

Study on the synthesis of nanosheets petal-shaped ZSM-5 Zeolites

In this work, a novel strategy for hydrothermal synthesis of nanosheets petal-shaped ZSM-5 zeolites was introduced. The experimental results indicated that the nanosheets petal-shaped ZSM-5 zeolites exhibited a higher specific surface area and more abundant acid sites. Under the synergistic crystallization effect of ethanol and seeds, the addition of CTAB promoted the growth of the layered structure, and the introduction of trace amounts of seeds effectively inhibited the growth of mordenite in a high alkalinity environment, reducing the crystallization time to 48 hours. More importantly, the petal-shaped ZSM-5 zeolites exhibited excellent MTP (Methanol-to-Propylene) catalytic performance, with methanol conversion maintained above 97.8 % for 80 hours and a maximum propylene selectivity of 49.1 %. This paper proposes an Ethanol-Seed-CTAB synthesis method for producing petal-shaped ZSM-5 zeolite with a unique morphology. This approach does not require the use of complex gemini quaternary ammonium surfactants in the synthesis process, greatly promoting the application and dissemination of nanosheets zeolites.

Surface engineered novel cationic surfactants with enhanced surface adsorption for environmental applications

Gemini Cationic Surfactants (GCS) have garnered significant attention due to their distinctive molecular structure, featuring two hydrophilic head groups associated with a hydrophobic spacer. This distinctive configuration enables diverse applications across various fields. Hence, the current study introduces a novel series of GCSs, ethanediyl-1,2-bis[di(2-hydroxypropyl) alkylammonium] dibromide (Cn-C2-Cn[IsoPr(OH)2; n = 9, 12 and 14) and comprehensively explore their properties, highlighting their promising antimicrobial activity. The synthesis of GCSs was validated using 1H NMR and IR spectroscopy. Dynamic Light Scattering was employed to determine the dimensions of Gemini surfactant aggregates in aqueous solutions. Surface tension analysis determined critical concentrations of micelle (CMC), minimum surface area (Amin) and concentration of surface excess (Γmax). Physicochemical properties were assessed through conductivity and surface tension analyses in aqueous solutions. The CMC, Amin and Γmax values decrease as alkyl chain length extends. Surface tension data revealed strong adsorption of GCSs at interfaces. π values (mN/m) ranged from 36.7 (C14C2C14[Iso-Pr(OH)]2) to 45.3 (C9C2C9[Iso-Pr(OH)]2). Conductivity and surface tension measurements further characterized Gemini surfactants in aqueous environments at 298 K. The size of the micelle aggregates varied between C9C2C9[Iso-Pr(OH)]2 (1.2885 nm) and C14C2C14[Iso-Pr(OH)]2 (1.9210 nm), highlighting the impact of chain length on micelle size. Hence, the study highlights significant effect of the chain lengths on Gemini cationic surfactants’ self-assembly in dilute aqueous environments. Antimicrobial tests demonstrated significant activity of Cn-C2-Cn[IsoPr(OH)]2 GCSs at varying concentrations. Antimicrobial tests showed the significant antimicrobial potential of these GCS compounds, suggesting their potential and promising applications in medical, hygiene, environmental sanitation and advanced materials sectors.

Impact of organic acid molecular length and structure on rock oil-wetting rapidity and stability

The oil-wetting properties of organic acids play a crucial role in various industrial applications, including enhanced oil recovery, oil spill remediation, surface modification, and so on. This study investigated the impact of organic acid molecular length and structure on oil-wetting rapidity and stability on sandstone and carbonate. Model oils prepared by dissolving organic acids in n-decane, and crude oil, were used as the oil phase. Their oil-wetting behavior was evaluated by contact angle values. The maximum molecular length of each organic acid was approximated based on its molecular structure. Our results indicate that organic acids change wettability much faster in carbonate rock than in sandstone. Longer organic acid molecules exhibit enhanced oil-wetting potential due to increased hydrophobic interactions with oil phases. Water film does not have a long-term impact on the oil-wetting process by organic acid on Indiana limestone. However, the existence of a water film largely inhibited the oil-wetting process for Indiana limestone in crude oil, and for Berea sandstone in crude and model oil. Furthermore, molecular structure, such as the presence of functional groups, significantly influences oil-wetting properties. Organic acids with an aromatic ring demonstrated a more stable oil-wetness against wettability alteration induced by surfactant treatment. Gemini surfactants with benzene ring(s) in the spacer removed aromatic organic acid more efficiently than surfactants without benzene ring. Overall, this study provides insights into the design and optimization of organic acids for applications requiring effective oil-wetting and oil-wetness stability, as well as the designing of surfactant structures with higher oil removal efficiency.

Ellipsoidal micelle formation of quaternary ammonium salt-based gemini surfactants: structural analysis through small-angle X-ray scattering.

Gemini surfactants exhibit better adsorption and aggregation properties than those of monomeric surfactants. However, to enhance the functional properties of gemini surfactants, the effect of spacer structures on their aggregation behavior must be elucidated. Small-angle X-ray scattering (SAXS) has been performed to study the aggregate structures of monomeric surfactants, but its application has not been expanded to the analysis of gemini surfactants. Therefore, in this study, we performed a structural analysis of aggregates formed by quaternary ammonium salt-based gemini surfactants with different spacer structures in aqueous solutions through viscosity, dynamic light scattering (DLS), and SAXS measurements. We also investigated the effects of the spacer structure and surfactant concentration on the aggregation behavior. The DLS results indicated that gemini surfactants with spacers containing cyclic structures, such as diethylene and triethylene chains, formed small micelles (several nanometers in size) at the limiting concentration for dissolution in water. In contrast, gemini surfactants with nitrogen and oxygen atoms at the center of the spacer formed ellipsoidal micelles at low concentrations, as shown by SAXS results. The core and overall radii of the minor and major axes of the ellipsoidal micelles decreased with increasing surfactant concentration and were larger for spacers with two ethylene chains connected to central nitrogen and oxygen atoms than for spacers with rigid diethylene and ethylene chains connected to a central nitrogen atom.

Antimicrobial and aggregation properties of asymmetric gemini surfactants based on 1-(2-hydroxypropyl)-4-ethyl piperazine and alkyl bromides

Asymmetric gemini surfactants were synthesized by the quaternization reaction of 1-(2-hydroxypropyl)-4-ethyl piperazine with (C9, C10, C12, and C14) alkyl bromides. The surface tension of their aqueous solutions was determined by the Du Nouy ring method and the conductometric method of specific electrical conductivity. According to the concentration dependence graphs of surface tension and specific electrical conductivity, critical micelle concentration – CMC, degree of association of the counterion – β, surface area occupied by the head group of the surfactant – Amin, maximum surface excess concentration – Γmax, effectiveness or surface pressure –πCMC, adsorption efficiency – pC20 were calculated, and the change of these parameters depending on the length of the alkyl chain was determined. Simultaneously, variations in Gibbs free energies of micellization and adsorption processes were computed. The diameters of aggregates formed by asymmetric gemini surfactants in water were determined by the DLS method. Antimicrobial abilities of asymmetric gemini surfactants against gram positive and gram negative bacteria and fungi were defined by the disk diffusion method.

Role of gemini surfactants with biodegradable spacer as efficient capping agents of silver nanoparticles

Since the last decade, silver nanoparticles (AgNPs) continue to attract interest of both academia and industry due to their peculiar physical, chemical, and optical properties. In the field of pharmaceutical applications, they are efficient carriers in the processes of controlled drug release, improve the drug's bioavailability, act as efficient antimicrobial agents and provide other biological functions conveyed at the nanometric scale. The known issue hampering further development of applications of AgNPs is their instability in aqueous environment. The present study utilizes two series of cationic bisammonium gemini surfactants with two dodecyl chains and a biodegradable spacer containing two amide or ester groups for the stabilization of AgNPs. The presence of nanosilver in the dispersions was confirmed by UV–VIS plasmon resonance spectra. Stability of AgNPs was characterized by zeta potential measurements proving that amide and ester gemini surfactant series are able to effectively stabilize AgNPs. The particles size analysis utilizing dynamic light scattering and scanning electron microscopy showed that AgNPs stabilized with flexible ester-based gemini surfactants have their size smaller than those capped with amide-containing gemini surfactants. Antimicrobial and anti-inflammatory activity determination as well as cytotoxicity experiments with gemini surfactant stabilized AgNPs showed a complex dependence of biological activity of AgNPs on the molecular structure of stabilizing agents.

Surface activity, aggregation behaviour and wettability of mixtures of perfluorobranched short-chain gemini quaternary ammonium surfactant and hydrocarbon anionic surfactants in dilute solution

The hydrophobic and oleophobic properties of perfluorobranched short chains are similar to those long chain fluorocarbons (fluorocarbon chain length ≥ 7), and their environmentally friendly properties make them good alternatives to traditional perfluorooctyl derivatives. For this purpose, a novel perfluorinated branched short chain quaternary ammonium gemini surfactant (PBFS) with high surface activity was synthesized, and the surface properties, aggregation behavior, wetting performance and adsorption performance of the complex system of PBFS and sodium octyl sulfate (SOS) were systematically studied. PBFS exhibited superior surface activity in aqueous solution with the critical micelle concentration (CMC) of 0.1667 mmol/L and the corresponding surface tension (γCMC) of 20.17 mN/m. Moreover, despite the fact that the mixing of PBFS and SOS was not ideal, the two still had the good synergistic effect: the CMC of the compounding solution was reduced to 0.0072 mmol/L and γCMC was 16.01 mN/m when the compounding ratio (CF: CH) was 1:8. And the composite solution could completely wet low surface energy polytetrafluoroethylene (PTFE) plates at 1 mmol/L, and could also wet PTFE plates at extremely low concentrations (0.0625 mmol/L), showing good wetting performance.

Cationic Gemini surfactants: a review on synthesis and their applications

Abstract The molecules of Gemini surfactants are dimeric and consist of two monomeric surfactant units linked by a spacer. Among them, cationic Gemini surfactants have a wide range of application in various industrial sectors such as pharmaceuticals, home and personal care, corrosion inhibition, etc. Various methods of synthesis have been investigated and tested for the synthesis of cationic Gemini surfactants. The surface properties of Gemini surfactants are highly dependent on various factors like spacer, headgroups, counterions, etc. The cationic Gemini surfactants have lower CMC values as compared to their monomeric analogues. This review highlights the different methods for the synthesis of cationic Gemini surfactants and the applications of these surfactants in different fields are presented.

Synthesis and Kinetics of CO2-Responsive Gemini Surfactants.

Surfactants are hailed as "industrial monosodium glutamate", and are widely used as emulsifiers, demulsifiers, water treatment agents, etc., in the petroleum industry. However, due to the unidirectivity of conventional surfactants, the difficulty in demulsifying petroleum emulsions generated after emulsification with such surfactants increases sharply. Therefore, it is of great significance and application value to design and develop a novel switchable surfactant for oil exploitation. In this study, a CO2-switchable Gemini surfactant of N,N'-dimethyl-N,N'-didodecyl butylene diamine (DMDBA) was synthesized from 1, 4-dibromobutane, dodecylamine, formic acid, and formaldehyde. Then, the synthesized surfactant was structurally characterized by infrared (IR) spectroscopy, hydrogen nuclear magnetic resonance (1H NMR) spectroscopy, and electrospray ionization mass spectrometry (ESI-MS); the changes in conductivity and Zeta potential of DMDBA before and after CO2/N2 injection were also studied. The results show that DMDBA had a good CO2 response and cycle reversibility. The critical micelle concentration (CMC) of cationic surfactant obtained from DMDBA by injecting CO2 was 1.45 × 10-4 mol/L, the surface tension at CMC was 33.4 mN·m-1, and the contact angle with paraffin was less than 90°, indicating that it had a good surface activity and wettability. In addition, the kinetic law of the process of producing surfactant by injecting CO2 was studied, and it was found that the process was a second-order reaction. The influence of temperature and gas velocity on the reaction dynamics was explored. The calculated values from the equation were in good agreement with the measured values, with a correlation coefficient greater than 0.9950. The activation energy measured during the formation of surfactant was Ea = 91.16 kJ/mol.

Aggregation behavior of newly synthesized Gemini cationic surfactants in absence and in presence of different inorganic salts in 15% DMSO–water solvent

In this study, three Gemini cationic surfactants related to thiazol-2-amine with three hydrocarbon chain lengths including 3-hexylthiazol-3-ium (TAC6), 3-dodecylthiazol-3-ium (TAC12) and octadecylthiazol3-ium (TAC18) were prepared. Surfactant structures were confirmed with IR and 1HNMR Spectroscopies. Critical micelle concentrations for all surfactants in 15% DMSO-Water solvent were measured using conductometric, refractometric, and densitometric techniques. Thermodynamics parameters were computed and explained. Also, enhancing properties of all surfactants were indicated under the effect of two concentrations, 0.001 M and 0.01 M, of six inorganic salts including Cl−, Br−, I−, Co+2, Cu+2, and Mn+2 radicals using conductivity and refractive index measurements. All techniques used to measure critical micelles concentration showed a good convergence in measuring CMC values and the behavior of all surfactants in 15% DMSO-water solvent. Increasing the binding constant of the counter ion and association constant reflects the effect of hydrocarbon chain length increment on enhancing micelle formation, where TAC 18 was shown as the lowest CMC in all applied measurements. Modeling the density of all surfactant solutions under study indicates an increase in hydrophobic polarizability with an increase in the molecular weight of the surfactant. Inorganic salts decreased the CMC of all surfactants with the increase in Gibbs free energy of micellization which ensures easier formation of more stable micelles in the presence of a salt solution. The effect of salts on decreasing CMC for all surfactants under study was arranged in the following order: Mn+2 < Cu+2 < Co+2 for cationic radicals and I− < Br− < Cl− for anionic radicals.

Synthesis of Newly Ester Type Gemini Cationic Surfactants: Surface Properties, Fabric Softness and Antibacterial Properties

AbstractFour ester cationic Gemini surfactants (EDQ‐n, n represents the carbon number in the raw fatty acid of 12, 14, 16 and 18) were synthesized from fatty acid, N, N‐dimethylethanolamine and 1, 4‐dibromobutane by two‐step reaction of esterification and quaternization. Their surface activities at air/water interface were investigated. The application performance such as water solubility, antistatic property, fabric softness, fabric whiteness, biodegradability, and antibacterial activities were tested and compared with traditional quaternary ammonium salt. The results showed that the γcmc increases with increasing the hydrophobic chain length and EDQ‐12 presented the highest surface activity. The diffusion coefficients calculated from the Ward‐Tordai equation indicates the adsorption process is a mixed‐diffusion kinetic adsorption mechanism. The water solubility of EDQ‐n is higher than dioctadecyl dimethyl ammonium chloride (D1821) and ester quaternary ammonium salt (Esterquats). The fabric softness and whiteness properties of EDQ‐16 and EDQ‐18 are similar to D1821 and Esterquats, which can significantly reduce the cotton fabric softness and have no significant difference in whiteness retention. EDQ‐n demonstrated more readily biodegradation(&gt;90 %) than D1821(0 %) after seven days. In addition, EDQ‐12 and EDQ‐14 show excellent antibacterial activities against Staphylococcus aureus and Escherichia coli in comparison with conventional bacteriostatic agent didecyl dimethyl ammonium chloride (DDAC).