Search Results (92)

Cationic surfactants, accounting for approximately 7% of the global surfactant market, are widely used in applications such as fabric softeners, biocides, and corrosion inhibitors. Recently, gemini surfactants—comprising two amphiphilic units linked by a spacer—have attracted significant interest due to their superior surface activity, lower critical micelle concentrations, and strong antimicrobial properties. However, their poor biodegradability, resulting from their complex molecular structure, has raised environmental concerns. To address this, researchers have developed ester-based gemini surfactants incorporating biodegradable bonds. This study aimed to investigate the relationship between the structure of ester-based gemini surfactants (hydrophobic chain length and spacer type) and their antimicrobial activity against bacteria and fungi. Three series of compounds featuring different functional groups in the spacer were synthesized, along with a trimeric surfactant for comparative purposes. The results demonstrated that both the hydrophobic chain length and the presence of additional cationic groups significantly influence the CMC and antimicrobial performance. Quantum mechanical calculations were also performed to search for correlations between electronic properties and chemical reactivity of compounds. These findings highlight that ester-based gemini surfactants combine high surface and antimicrobial activity with the potential for improved biodegradability, making them promising candidates for use in environmentally friendly applications. Full article

To investigate the specific performance enhancement of oilfield surfactants by using sodium p-aminobenzenesulfonate as a connecting group, cationic surfactant N,N-dimethyl-N-(oxiran-2-ylmethyl)dodecan-1-aminium (DDPA) and zwitterionic gemini surfactant sodium 4-[bis(3-(dodecyldimethylamino)-2-hydroxypropyl)amino]benzenesulfonate (DDBS) were synthesized. The oil recovery performance of these surfactants was compared, revealing that DDBS outperforms DDPA in thermal stability, wettability, adsorption, and resistance to temperature and salinity variations, as well as surface/interface activity, except for emulsification. Core flooding experiments, simulating the conditions of the Xinjiang oilfield, demonstrated that DDBS can achieve the same enhanced oil recovery effect at a concentration that is 1/15 of that of DDPA. Compared with water, DDBS and DDPA can incrementally enhance recovery rates by 7.9% and 8.5%. Furthermore, the synergistic formulation of DDBS with sodium dodecylbenzenesulfonate (SDS) significantly optimized performance, achieving a reduction in interfacial tension to 0.0301 mN m⁻¹. This study provides a research and data foundation for the application of new surfactants in petroleum extraction. Full article

Background/Objectives: Mixed bloodstream infections associated with central venous catheter (CVC) use are a growing problem. The aim of this study was to evaluate the activity of a cationic arginine-based gemini surfactant, C₉(LA)₂, against mixed biofilms of fluconazole-resistant Candida albicans and extended-spectrum beta-lactamase (ESBL)-producing E. coli, and the preventive effect of this surfactant impregnated in CVCs on the formation of inter-kingdom biofilms. Methods: Broth microdilution assays were performed along with evaluation of the effect against mixed biofilms in formation. The impregnation of CVCs with the surfactant and with a hydrogel containing the cationic surfactant was investigated to assess their potential to prevent the formation of mixed biofilms. Scanning electron microscopy (SEM) was also utilized. Results: Minimum inhibitory concentrations (MICs) for resistant C. albicans ranged from 4–5.3 µg/mL, while for E. coli, the MICs varied from 85.3 to 298.7 µg/mL. Fungicidal and bactericidal action patterns were obtained. In mixed biofilm formation in 96-well plates, there was a significant reduction in the colony-forming unit (CFU) count. The impregnation of the CVC with C₉(LA)₂ alone resulted in a biofilm reduction of 62% versus C. albicans and 48.7% against E. coli in terms of CFUs. When the CVC was impregnated with the surfactant hydrogel, the effect was improved with an inhibition of 71.7% for C. albicans and 86.7% for E. coli. The images obtained by SEM corroborated the results. Conclusions: C₉(LA)₂ has potential for use in CVC impregnation to prevent the formation of mixed biofilms of fluconazole-resistant C. albicans and ESBL-producing E. coli. Full article

Mesoporous silica sieves have been prepared through sol–gel synthesis using diester gemini surfactants as pore templates, aiming to obtain new materials with potential use for water remediation. A series of mesoporous spherical silica particles of submicron size have been prepared in an alkali-catalyzed reaction, using a tetraethyl orthosilicate precursor and bis-quaternary ammonium gemini surfactants with diester spacers of varied lengths as pore-forming agents. The effect of the spacer length on the particle morphology was studied using nitrogen porosimetry, small-angle X-ray scattering (SAXS), ultra-small-angle neutron scattering, scanning, and transmission electron microscopy (SEM, TEM). The results revealed that for all spacer lengths, a long-range hexagonal pore ordering developed in the materials. The silica particles were nearly spherical, with sizes below 1 micrometer, and a weak dependence of the mean particle size on the spacer length could be observed. The template removal procedure had a strong influence on the porosity: calcination caused a moderate shrinkage of the pores while retaining the hexagonal structure, whereas treatment with acidified ethanol resulted in only partial removal of the surfactants; however, the hexagonal structure was severely destroyed. The applicability of the obtained calcined materials as adsorbents for heavy metal ions from water was studied with the example of Pb(II). A high sorption capacity of 110 mg/g was obtained in batch experiments, at pH 5 and 4 h contact time. Full article

Cationic gemini surfactants are used due to their broad spectrum of activity, especially surface, anticorrosive and antimicrobial properties. Mixtures of cationic and anionic surfactants are also increasingly described. In order to investigate the effect of anionic additive on antimicrobial activity, experimental studies were carried out to obtain MIC (minimal inhibitory concentration) against E. coli and S. aureus bacteria. Two gemini surfactants (12-6-12 and 12-O-12) and two single quaternary ammonium salts (DTAB and DDAC) were analyzed. The most commonly used commercial compounds of this class, i.e., SDS and SL, were used as anionic additives. In addition, computer quantum mechanical studies were also carried out to confirm the relationship between the structure of the mixture and the activity. The obtained results of microbiological tests and quantum mechanical calculations are in agreement with each other and show the lack of synergism in catanionic mixtures in the case of antibacterial activity. Full article

The present work is devoted to the synthesis and analysis of the physicochemical properties of new functionalized asymmetric Gemini surfactants. Herein, alkyl- and azide-substituted surfactants with symmetric and asymmetric substituents were synthesized by using the click-reaction method. The critical aggregation concentration values of Gemini surfactants were determined. The binding processes of functionalized Gemini surfactants with bovine serum albumin were evaluated by fluorescence spectroscopy. Also, using the temperature dependences of the binding constants, the mechanism of Gemini surfactants binding with bovine serum albumin was studied. The hydrodynamic diameters of the formed bovine serum albumin/surfactant aggregates were analyzed. Based on electrophoretic light scattering, the ability of the synthesized Gemini surfactants to form associates was analyzed. The possibility of changing the mechanism of interaction in the 15c/bovine serum albumin system was shown. Based on the results obtained using different light scattering techniques and fluorescence spectroscopy, the mechanisms of interaction between bovine serum albumin and surfactants were determined. Full article

Three types of coatings (contact-based, release-based, and combined coatings with both contact-based and release-based actions) were prepared and tested for the ability to inactivate SARS-CoV-2. In these coatings, quaternary ammonium surfactants were used as active agents since quaternary ammonium compounds are some of the most commonly used disinfectants. To provide contact-based action, the glass and silicon surfaces with covalently attached quaternary ammonium cationic surfactant were prepared using a dimethyloctadecyl[3-(trimethoxysilyl)propyl]ammonium chloride modifier. Surface modification was confirmed by attenuated total reflection infrared spectroscopy, X-ray photoelectron spectroscopy (XPS), scanning electron microscopy, and contact angle measurements. The grafting density of the modifier was estimated by XPS and elemental analysis. To provide release-based action, the widely used quaternary ammonium cationic disinfectant, benzalkonium chloride (BAC), and a newly synthesized cationic gemini surfactant, C18-4-C18, were bound non-covalently to the surface either through hydrophobic or electrostatic interactions. Virus titration revealed that the surfaces with combined contact-based and release-based action and the surfaces with only release-based action completely inactivate SARS-CoV-2. Coatings containing only covalently bound disinfectant are much less effective; they only provide up to 1.25 log10 reduction in the virus titer, probably because of the low disinfectant content in the surface monolayer. No pronounced differences in the activity between the flat and structured surfaces were observed for any of the coatings under study. Comparative studies of free and electrostatically bound disinfectants show that binding to the surface of nanoparticles diminishes the activity. These data indicate that SARS-CoV-2 is more sensitive to the free disinfectants. Full article

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. Full article

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. Full article

Cationic gemini surfactants have emerged as potential gene delivery agents as they can co-assemble with DNA due to a strong electrostatic association. Commonly, DNA complexation is enhanced by the inclusion of a helper lipid (HL), which also plays a key role in transfection efficiency. The formation of lipoplexes, used as non-viral vectors for transfection, through electrostatic and hydrophobic interactions is affected by various physicochemical parameters, such as cationic surfactant:HL molar ratio, (+/−) charge ratio, and the morphological structure of the lipoplexes. Herein, we investigated the DNA complexation ability of mixtures of serine-based gemini surfactants, (nSer)₂N5, and monoolein (MO) as a helper lipid. The micelle-forming serine surfactants contain long lipophilic chains (12 to 18 C atoms) and a five CH₂ spacer, both linked to the nitrogen atoms of the serine residues by amine linkages. The (nSer)₂N5:MO aggregates are non-cytotoxic up to 35–90 µM, depending on surfactant and surfactant/MO mixing ratio, and in general, higher MO content and longer surfactant chain length tend to promote higher cell viability. All systems efficaciously complex DNA, but the (18Ser)₂N5:MO one clearly stands as the best-performing one. Incorporating MO into the serine surfactant system affects the morphology and size distribution of the formed mixed aggregates. In the low concentration regime, gemini–MO systems aggregate in the form of vesicles, while at high concentrations the formation of a lamellar liquid crystalline phase is observed. This suggests that lipoplexes might share a similar bilayer-based structure. Full article

In this study, we present a comprehensive first-principles computational investigation focused on the structural characteristics, electronic properties, and coupling integrations of three cationic Gemini surfactants: 12-4-12, 12-3-12, and 12-2-12 ((CH₃(CH₂)₁₁)(CH₃)₂-N⁺-(CH₂)_n-N⁺(CH₃(CH₂)₁₁)(CH₃)₂, where n = 2, 3, or 4). By employing Density Functional Theory (DFT) computations, we aimed to gain insights into the fundamental aspects of these surfactant molecules, and the intermolecular interactions among these surfactant molecules. We examined different conformers of each surfactant, including parallel, wing, and bent conformers, and compared their relative stability and properties. We elucidated that the complex structural characteristics, electronic properties, and molecular arrangements of the surfactants vary according to the number of carbon atoms in the central spacer. We also conducted experimental Raman spectroscopy on the three surfactants to compare the results with our computational findings. Furthermore, we computed the coupling behaviors of different conformers of 12-4-12 surfactants in order to gain insights into their coupling mechanism. Full article

The rapid industrial development of civilization has led to the need for the development of new materials to clean up chemically contaminated wastewater and soils. Organoclays, based on smectite minerals and various types of surfactants, are one of the most effective sorbents for adsorbing organic and inorganic pollutants. Organoclays are clay minerals that have been modified by the intercalation or grafting of organic molecules. The main mechanism of interaction between organic substances and organoclays involves the adsorption of the substances onto the surface of the clay mineral, which has an expanded structural cell. Various types of surfactants can be used to synthesize organoclays, including cationic, anionic, and amphoteric surfactants. Each type of surfactant has different properties that affect the clay’s ability to sorb. Cationic forms of trace elements, such as heavy metals, can also be adsorbed by organoclays. Data on the adsorption of these substances by organoclays are provided, along with information on how to synthesize them using various surfactants. This review also discusses the main mechanisms of interaction between these substances and clays and the various methods used to create organoclays. It is clear that the adsorption of heavy metals by organoclays is not influenced by their structure or properties, as they belong to the category of surfactant, but rather by their overall chemical structure and characteristics. The wide variety of surfactant types leads to different effects on the adsorption properties of trace elements. Full article

The use of surfactants in oil recovery can effectively improve crude oil recovery rate. Due to the enhanced salt and temperature resistance of surfactant molecules by non-ionic chain segments, anionic groups have good emulsifying stability. Currently, there are many studies on anionic non-ionic surfactants for oil recovery in China, but there is relatively little systematic research on introducing EOs into hydrophobic alkyl chains, especially on their self-assembly behavior. This article proposes a simple and effective synthesis method, using 3-aminopropane sulfonic acid, fatty alcohol polyoxyethylene ether, and epichlorohydrin as raw materials, to insert EO into hydrophobic alkyl chains and synthesize a series of new anionic non-ionic Gemini surfactants (CnEO-5, n = 8, 12, 16). The surface activity, thermodynamic properties, and self-assembly behavior of these surfactants were systematically studied through surface tension, conductivity, steady-state fluorescence probes, transmission electron microscopy, and molecular dynamics simulations. The surface tension test results show that CnEO-5 has high surface activity and is higher than traditional single chain surfactants and structurally similar anionic non-ionic Gemini surfactants. Additionally, thermodynamic parameters (e.g., ΔG°_mic ΔH°_mic ΔS°_mic et al. indicate that CnEO-5 molecules are exothermic and spontaneous during the micellization process. DLS, p-values, and TEM results indicate that anionic non-ionic Gemini surfactants with shorter hydrophobic chains (such as C8EO-5) tend to form larger vesicles in aqueous solutions, which are formed in a tail to tail and staggered manner; Negative non-ionic Gemini surfactants with longer hydrophobic chains (such as C12EO-5, C16EO-5) tend to form small micelles. The test results indicate that CnEO-5 anionic non-ionic Gemini surfactants have certain application prospects in improving crude oil recovery. Full article

Drug delivery vehicles composed of lipids and gemini surfactants (GS) are promising in gene therapy. Tuning the composition and properties of the delivery vehicle is important for the efficient load and delivery of DNA fragments (genes). In this paper, we studied novel gene delivery systems composed of 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC), 1,2-dipalmitoyl-sn-3-phosphocholine (DPPC), and GS of the type N,N-bis(dimethylalkyl)-$\alpha ,\omega$-alkanediammonium dibromide at different ratios. The nanoscale properties of the mixed DOPC–DPPC–GS monolayers on the surface of the gene delivery system were studied using atomic force microscopy (AFM) and Kelvin probe force microscopy (KPFM). We demonstrate that lipid–GS mixed monolayers result in the formation of nanoscale domains that vary in size, height, and electrical surface potential. We show that the presence of GS can impart significant changes to the domain topography and electrical surface potential compared to monolayers composed of lipids alone. Full article

In the last decade, hydrogels for hydraulic fracturing based on viscoelastic surfactants have been actively studied. Interest in these systems is justified by their unique qualities: good viscoelasticity and the ability to form stable suspensions of proppant or sand, destruction without the formation of bridging agents, hydrophobization of the rock surface and metal of technological equipment, as well as oil-cleaning properties. These qualities are most often provided by a minimum set of components—a surfactant and an electrolyte. However, the absence of a polymer limits the use of these gels in formations where fluid leakoff is possible. In this article, a liquid was studied, based on a pseudo gemini surfactant (PGVES) with the addition of a water-soluble polysaccharide. The objects of study were selected based on the assumption of interactions between PGVES and the polymer; interactions which favorably influence the technological characteristics of the fracturing fluid. To confirm the hypothesis, rheological studies were carried out. These included rotational viscometry and oscillatory studies at various temperatures. The settling velocity of particles of various proppant fractions was studied and tests were carried out to assess fluid leakoff. The performed experiments show an improvement in the characteristics of the PGVES-based gel under the influence of the polysaccharide. In particular, the rheological properties increase significantly, the stability of proppant suspensions improves, and the fluid leakoff of systems decreases, all of which expands the possibility of using these fracturing fluids and makes this area of experimentation promising. Full article