Commercial Cationic Surfactant Research Articles

New aqueous two-phase system formed by piperazinium-based surface-active ionic liquid for extraction of dyes

Aqueous two-phase systems (ATPSs) as alternatives to traditional liquid–liquid extraction systems have been used intensively in recent years. In this work, a new ATPS composed of a piperazinium-based surface-active ionic liquid (SAIL), 1-(2-hydroxyethyl)piperazinium laurate ([HEP][C11CO2]), and a commercial cationic surfactant, dodecyldimethylbenzylammonium chloride (DDBAC) was prepared. The phase diagram for the ternary system DDBAC + [HEP][C11CO2] + H2O was determined, and the effects of composition and temperature on phase behaviors and properties were investigated. Phase separation was found spontaneous and thermodynamically favored when the mass fraction of water (w3) exceeded 0.60, primarily due to the salting-out of the hydrophilic ions [HEP]+ and Cl− in the bottom phase. Micelles were observed in the top phase where high concentrations of the hydrophobic ions [DDBA]+ and [C11CO2]− were present. Increasing the water content at a fixed surfactant-to-SAIL molar ratio resulted in a decreased top phase volume, while the extraction efficiency (EE) and the distribution coefficient (D) were both increased for extractions of Basic Blue 7 and Allura Red AC. When w3 reached 0.96 and the initial concentration of dye was below 1 × 10−4 mol·L−1, the EE values exceeded 98 % with all the D values surpassing 100, indicating the promising potential for SAIL-ATPS applications.

A win-win scenario for antibacterial activity and skin mildness of cationic surfactants based on the modulation of host-guest supramolecular conformation

The commercial cationic surfactants (CSAa) with quaternary ammonium (QA) groups have proved to be broad-spectrum bactericide against bacteria, fungi, and viruses. Nevertheless, they inevitably exhibit potent irritation on the skin. In this work, we systematically investigated the regulatory mechanism of the host-guest supramolecular conformation with β-cyclodextrin (β-CD) on the bactericidal performance and skin irritation of CSAa with different head groups and chain lengths. When the ratio of incorporated β-CD is not greater than 1:1, the bactericidal efficiency of CSAa@β-CD (n > 12) remained above 90 % due to the free QA groups and hydrophobic fraction that can act on negatively charged bacterial membranes. And once the ratio of β-CD exceeded 1:1, the β-CD attracted to the bacterial surface by hydrogen bonding might prevent CSAa@β-CD from acting on bacteria, resulting in a decrement in antibacterial performance. Even so, the antibacterial activity of CSAa with long alkyl chains (n = 16, 18) was independent from the complexation of β-CD. Accordingly, both the zein solubilization assay and the neutrophil migration assay on zebrafish skin evidenced that β-CD attenuated the interaction of surfactant with skin model proteins and the inflammatory effect on zebrafish, thereby enhancing skin mildness. In this way, we hope to create a simple but effective brainpower using the host-guest approach to guarantee both bactericidal efficiency and skin mildness without modifying the chemical structure of these commercial biocides.

Designing of quaternized hyperbranched polyamidoamines dendrimers: Surface activity, pharmaceutical efficacy, and safety approach

The low solubility of the drug considers a major challenge for pharmaceutical formulation of both oral and parenteral products. In this work various generations of cationic hyperbranched polyamidoamine (PAMAM) quaternary ammonium salt dendrimers terminated with amine end groups were synthesized. The pharmaceutical application of these quaternized cationic surfactants ended with amine end groups and those ended with ester end groups which prepared in an earlier study were investigated. These dendrimers were compared as solubilizing agents for coenzyme Q10 (poorly soluble drug) and the dendrimers that showed high solubilizing potential (G2.5 C8, G2.5 C12) were selected to be evaluated as a dendrimer in dissolution study for coenzyme Q10 or Ledipasvir drug. In our investigation a comparison between four dissolution media with different surfactants namely, G2.5 C8, G2.5 C12, CTAB and Labrasol used for the dissolution test of Q10 was carried out. The results revealed that % Q10 released after 4 h was 86.7, 70.5, 43 and 10.5% for these dissolution media, respectively. These results indicated the priority of the synthesized cationic surfactants than the known commercial cationic surfactant (CTAB) or than Labrasol as recommended surfactant in previous lectures. Therefore, the profiles of the ledipasvir dissolution in the three-dissolution media (G2.5 C8, G2.5 C12 and FDA surfactant (1.5% tween 80 and 0.0075 mg/ml Butylated Hydroxytoluene (BHT)) are similar. The obtained results emphasized that the new surfactants can be used as alternative to FDA surfactant in the dissolution media of Ledipasvir.Eventually, the toxicity study was performed for two selected compounds from the prepared dendrimers, and these compounds were proved to be safe.

Gemini Surfactant as a Template Agent for the Synthesis of More Eco-Friendly Silica Nanocapsules

Silica mesoporous nanocapsules are a class of “smart” engineered nanomaterials (ENMs) applied in several fields. Recent studies have highlighted that they can exert deleterious effects into marine organisms, attributed to the use of the toxic cationic surfactant N-hexadecyl-N,N,N-trimethylammonium bromide (CTAB) during the synthesis of ENMs. The present study reports the successful synthesis and characterization of novel gemini surfactant-based silica nanocapsules. The gemini surfactant 1,4-bis-[N-(1-dodecyl)-N,N-dimethylammoniummethyl]benzene dibromide (QSB2-12) was chosen as a more environmentally-friendly replacement of CTAB. Nanocapsules were characterized by scanning electron microscopy (SEM), Fourier-transformed infrared spectroscopy (FTIR), dynamic light scattering (DLS), thermogravimetric analysis (TGA) and N2 adsorption-desorption isotherms. Short-term exposure effects of new ENMs were evaluated in four marine species (Nannochloropsis gaditana, Tetraselmis chuii and Phaeodactylum tricornutum) and the microcrustacean (Artemia salina). The replacement of the commercial cationic surfactant by the gemini surfactant does not change the structure nor the environmental behaviour in seawater of the newly synthesised silica nanocontainers. Additionally, it is demonstrated that using gemini surfactants can reduce the toxicity of novel silica nanocapsules towards the tested marine species. As a result, environmentally-friendly ENMs can be obtained based on a safe-by-design approach, thereby fitting the concept of Green Chemistry.

Environmental behaviour and ecotoxicity of cationic surfactants towards marine organisms

Cationic surfactants are surface-active compounds that can be found in many products, including household and cleaning agents. As a consequence, they tend to be discarded into water streams, ultimately ending up in the aquatic environment. In spite of this environmental issue, studies describing their effects towards marine species are lacking. The aim of this study was therefore to evaluate the short-term exposure effects of two commercial cationic surfactants and three novel gemini surfactants on four marine species, the green microalgae Nannochloropsis gaditana and Tetraselmis chuii, the diatom Phaeodactylum tricornutum, and the crustacean Artemia salina. Furthermore, biodegradation and size distribution of the cationic surfactants in artificial seawater were also studied by UV–vis spectrophotometry and dynamic light scattering, respectively.Ecotoxicity tests revealed that the commercial cationic surfactant N-cetyl-N,N,N-trimethylammonium bromide is toxic to all tested marine species while N-dodecyl-N,N,N-trimethylammonium chloride and 1,4-bis-[N-(1-dodecyl)-N,N-dimethylammoniummethyl]benzene dibromide showed the lowest toxicity among the tested cationic surfactants. Besides the novel insights regarding the effects caused by these five cationic surfactants, this work opens prospects for the replacement of commercially available surfactants by more environmentally friendly alternatives.

Unique Interfacial Phenomena on Macroscopic and Colloidal Scales Induced by Two-Dimensional Phase Transitions.

This feature article addresses a variety of unique macroscopic-scale and colloidal-scale interfacial phenomena, such as wetting transitions of oil droplets into molecularly thin films, spontaneous merging and splitting of oil droplets at air-water interfaces, solid monolayer and bilayer formation in mixed cationic surfactant/alkane adsorbed films, switching of foam-film thickness, and oil-in-water emulsion stability. All of these phenomena can be observed using commercial cationic surfactants, liquid alkanes, and water.

Reducing nitrogen loss by application of natural clinoptilolite modified with quaternary N-Alkyl agent as controlled-release fertilizer in two species of beans (P. Vulgaris and Vigna Unguiculata)

ABSTRACTIn this work, a novel controlled-release fertilizer (CRF) was designed by using new quaternary N-alkyl as an innovative surface modifier for clinoptilolite in order to adsorb the nitrate anion. So far, a few number of commercial cationic surfactants have been introduced for engineered zeolites to adsorb and slow release anions. Therefore, an organic ligand was synthesized for the first time and was applied for modification of clinoptilolite. Investigating the effect of pH and adsorbent dosage showed that the experimental adsorption data were fitted well with the Langmuir and Freundlich isotherm models. Moreover, nitrate leaching tests were performed and the results confirmed that nitrate concentration of the leachate from the soil amended with novel fertilizer was 42% lower than that of the urea fertilizer. The growth parameters including were studied and the results showed that the red beans planted in the soil amended with modified fertilizer had the best results.

Spectroscopically probing the effects of Holmium(III) based complex counterion on the dye-cationic surfactant interactions

Interactions between dyes and surfactants is a well-established research area. It is important to interpret the missing links related to the differences between the relatively newer surfactant entrants with respect to their modified counterions and their conventional counterparts. In this research, we explored and compared the interactions of a commercial cationic surfactant dodecyltrimethylammonium bromide (DTAB) and a modified surfactant having optically active counterion, trichlromonobromoholminate, with model dyes methyl orange (MO) and eriochrome black T (EBT). The effect of a cationic surfactant DTAB and the same surfactant with modified counterion dodecyltrimethylammonium tricholomonobromoholminate (DTAH) on the electronic properties of model azo dyes MO and EBT were studied in the premicellar and postmicellar concentrations of surfactants. UV–Visible (UV–Vis) and steady state fluorescence spectroscopies (SSF) were employed to probe the interactions between dyes and surfactants. The binary associations were rationalized by quantitative mathematical models including benesi-hildebrand and stern volmer equations. The variations in the dye electronic properties caused by the two counterions were estimated by various parameters including, binding constants, ka and kb, binding affinity ‘a’ and Gibbs free energy of binding ΔGb. The results show that extent of binding of modified surfactant DTAH with dye is reduced when compared to conventional cationic surfactant DTAB. Moreover, the study sheds light on the impact of inorganic counterion on solubilization of dyes and possible locus of dye as well as counterion in the modified micellar and pre-miceller systems. [HoCl3Br]−1 counterion clearly alter the optical response of MO and EBT dyes in the presence of surfactant system due to the formation of complex by Holmium(III) and azo dyes.

Successful application of a commercial cationic surfactant mixture (benzalkonium chloride) as porosity stabilizer in porous carbons fabrication

Porous carbons (BSPCs) were obtained by carbonization of resorcinol-formaldehyde gels in the presence of cationic surfactants mixture (benzalkonium chloride) which act as porosity stabilizer. The application of an inexpensive industrial grade surfactant mixture as porosity stabilizer permits obtaining porous carbons with well-developed micro and mesoporosity at low cost. The stabilizing effect on the sol–gel nanostructure allows maintaining the gels porosity during conventional air drying, simplifying the production of porous carbon by making unnecessary complex drying procedures (e.g. supercritical drying), cumbersome solvent exchanges, and long curing times. The carbonization process of BSPCs studied by TGA shows that the stabilizer and non-carbon elements (hydrogen and oxygen) are only eliminated during pyrolysis at temperature above 600°C. The BSPCs morphological and textural properties were studied by scanning electron microscopy and nitrogen physisorption isotherms. The BSPCs present large specific surface areas (up to 645m2/g) containing mesopores and micropores. Furthermore, the pore distribution and morphology depend on the monomer (resorcinol) to stabilizer (benzalkonium chloride) ratio. Cyclic voltammetry and electrochemical impedance spectroscopy were employed to study the electrochemical properties of the carbon materials. The BSPCs exhibit a large specific capacitance (up to 179F/g at 2.8mHz in 1M H2SO4) The results suggest that porosity stabilization of resorcinol/formaldehyde gels could be performed using different cationic surfactants, even commercial mixtures like benzalkonium chloride.

Biocatalytic synthesis, antimicrobial properties and toxicity studies of arginine derivative surfactants.

Two novel arginine-based cationic surfactants were synthesized using as biocatalyst papain, an endopeptidase from Carica papaya latex, adsorbed onto polyamide. The classical substrate N (α)-benzoyl-arginine ethyl ester hydrochloride for the determination of cysteine and serine proteases activity was used as the arginine donor, whereas decyl- and dodecylamine were used as nucleophiles for the condensation reaction. Yields higher than 90 and 80% were achieved for the synthesis of N (α)-benzoyl-arginine decyl amide (Bz-Arg-NHC10) and N (α)-benzoyl-arginine dodecyl amide (Bz-Arg-NHC12), respectively. The purification process was developed in order to make it more sustainable, by using water and ethanol as the main separation solvents in a single cationic exchange chromatographic separation step. Bz-Arg-NHC10 and Bz-Arg-NHC12 proved antimicrobial activity against both Gram-positive and Gram-negative bacteria, revealing their potential use as effective disinfectants as they reduced 99% the initial bacterial population after only 1h of contact. The cytotoxic effect towards different cell types of both arginine derivatives was also measured. Bz-Arg-NHCn demonstrated lower haemolytic activity and were less eye-irritating than the commercial cationic surfactant cetrimide. A similar trend could also be observed when cytotoxicity was tested on hepatocytes and fibroblast cell lines: both arginine derivatives were less toxic than cetrimide. All these properties would make the two novel arginine compounds a promising alternative to commercial cationic surfactants, especially for their use as additives in topical formulations.

Self-assembled switching gels with multiresponsivity and chirality.

A multiresponsive hydrogel material consisting of a commercial cationic surfactant and an azobenzene derivative functionalized with four carboxylic acid groups was constructed. The achiral azobenzene molecule as a gelator produces chirality at the supramolecular level in the presence of H(+). The acid-induced gelation and morphology change of supramolecular gels were investigated in detail by cryogenic transmission electron microscopy (cryo-TEM), rheological measurements, circular dichroism (CD), and (1)H NMR spectra. Based on the results, a mechanism of the intermolecular H-bond-directed gelation and supramolecular chirality was proposed. Other than the pH sensitivity, the microstructure and the chirality of the hydrogel demonstrate reversible switching behavior in response to photoirradiation, on account of the photoisomerization of the azobenzene derivative. Accordingly, a chiroptical switch comprising four different states in response to pH and light stimuli is strategically constructed. Not only does the present system provide a good opportunity for investigating the gelation-induced supramolecular chirality by symmetry breaking totally based on achiral molecules, but it also proposes a new strategy to build multiresponsive supramolecular switches as particularly attractive for the future development of functional materials.

Physicochemical Characterization and Self-Assembly Studies on Cationic Surfactants Bearing mPEG Tail

Poly(ethylene glycol), PEG, is normally coupled to hydrophobic molecules to produce nonionic surfactants. However, there is no report so far on cationic surfactants in which PEG chain acts as a hydrophobic tail. In this work, two novel cationic amphiphiles containing a poly(ethylene glycol) monomethyl ether (mPEG) tail of different lengths linked to a cationic headgroup were synthesized to investigate their surface activity and self-assembling properties. The amphiphiles were shown to be surface-active with low critical micelle concentration (cmc). It has been found that although mPEG chain is hydrophilic as compared to hydrocarbon chain of equivalent length, the cmc values are lower than that of cetyltrimethylammonium chloride, a commercial cationic surfactant. The cationic surfactants have been shown to have antimicrobial activity. The fluorescence probe studies and the thermodynamic data have shown that the self-assembly is due to strong van der Waals interaction between mPEG chains as well as hydrophobic effect. The single-tailed cationic surfactants spontaneously self-assembled to form small unilamellar vesicles with hydrodynamic diameter in the range of 20-50 nm. The vesicles were characterized by fluorescence probe technique, dynamic light scattering, transmission electron microscopy, and confocal fluorescence microscopy. We have also studied encapsulation of model drugs by the vesicles and pH-triggered release kinetics.

Development and characterization of nanocapsules comprising dodecyltrimethylammonium chloride and κ-carrageenan

The aim of this work was to develop and characterize a new type of nanocapsules. To this end, a nanoemulsion bearing an oily core (Miglyol 812) was obtained by spontaneous emulsification and stabilized by dodecyl-trimethylammonium chloride (DTAC), a commercial cationic surfactant; this nanoemulsion was coated with proportionally very small amounts of κ-carrageenan (at molar charge ratios of Z ≤ 0.0045) that interact predominantly by an electrostatic mechanism with the positively charged sites at the polar heads of DTAC at the nanoemulsion's surface to harness nanocapsules of average size ~250-330 nm and zeta potential (ζ) ranging from ~+80 to +7 mV. The potential application of the new type of developed nanosystems as drug delivery vehicles has yet to be investigated and fully realized.

Dynamic Properties of Cationic Diacyl-Glycerol-Arginine-Based Surfactant/Phospholipid Mixtures at the Air/Water Interface

In this Article, we study the binary surface interactions of 1,2-dimyristoyl-rac-glycero-3-O-(N(alpha)-acetyl-L-arginine) hydrochloride (1414RAc) with 1,2-dipalmitoyl-sn-glycero-3-phosphatidylcholine (DPPC) on 0.1 M sodium chloride solutions. 1414RAc is a novel monocationic surfactant that has potential applications as an antimicrobial agent, is biodegradable, and shows a toxicity activity smaller than that of other commercial cationic surfactants. DPPC phospholipid was used as a model membrane component. The dynamic surface tension of 1414RAc/DPPC aqueous dispersions injected into the saline subphase was followed by tensiometry. The layer formation for the mixtures is always accelerated with respect to DPPC, and surprisingly, the surface tension reduction is faster and reaches lower surface tension values at surfactant concentration below its critical micellar concentration (cmc). Interfacial dilational rheology properties of mixed films spread on the air/water interface were determined by the dynamic oscillation method using a Langmuir trough. The effect of surfactant mole fraction on the rheological parameters of 1414RAc/DPPC mixed monolayers was studied at a relative amplitude of area deformation of 5% and a frequency of 50 mHz. The monolayer viscoelasticity shows a nonideal mixing behavior with predominance of the surfactant properties. This nonideal behavior has been attributed to the prevalence of electrostatic interactions.

Reduction and turbulence characteristics in sub-zero temperature range of cationic and zwitterionic surfactants in EG/water solvent

The addition of small amounts of surfactant to a solvent in turbulent flow can reduce friction drag greatly. A new approach to energy savings in district cooling systems is to use surfactant solutions at subzero temperatures as the cooling fluids. In this paper, experiments were conducted to study the drag-reduction performances of a commercial cationic surfactant solution (oleylmethylbiss-hydroxyethyl ammonium chloride) and a newly synthesized zwitterionic surfactant solution (oleyl trimethylaminimide) in a two-dimensional channel. For testing the drag reduction at subzero temperatures, for which little data have been reported and none in channel flow, a 20% ethylene glycol aqueous solution (EG/W) was used as a solvent. The surfactant concentration ranged from 50 to 1000 ppm and the temperatures were –5 and 25°C. The turbulence features of the surfactant drag-reducing flow were measured by using the PIV (particle image velocimetry) technique. It was found that both surfactant solutions showed drag-reducing characteristics, which were affected by concentration and temperature. The maximum drag reduction was 83% at 25°C for the 200 ppm zwitterionic surfactant solution. Compared with EG/W turbulent flow, the addition of surfactant suppressed the turbulent intensities and vortex fluctuations and the Reynolds stresses were zero. The effects of addition of NaNO2 to the surfactant solutions were also investigated.

Straightforward Method for the Preparation of Lysine-Based Double-Chained Anionic Surfactants

Double-chained surfactants with potential biocompatibility have been prepared in high yields by lysine acylation with four natural saturated fatty acids (C6 to C12) and with cis-undec-5-enoic acid. The surfactants were found to assemble into nanotubules in aqueous medium and, when mixed with a commercial cationic surfactant, to spontaneously form liposomes.

Synthesis and rheological properties of polystyrene/layered silicate nanocomposite

Exfoliated polystyrene (PS)/organo-modified montmorillonite (MMT) nanocomposites were synthesized through in situ free radical bulk polymerization by dispersing a modified reactive organophilic MMT layered silicate in styrene monomer. The original MMT was modified by a mixture of two commercial cationic surfactants, [2-(acryloyloxy)ethyl](4-benzoylbenzyl)dimethylammonium bromide (ADAB) and cetyltrimethylammonium bromide (CTAB), with the former containing a polymerizable vinyl group. The exfoliating and intercalating structures were probed by X-ray diffraction (XRD) and transmission electron microscopy (TEM). Comparing with pure PS, the nanocomposites show much higher decomposition temperature, higher dynamic modulus, stronger shear thinning behavior and a smaller die swell ratio. The leveling-off of the storage modulus at low frequencies in the oscillatory shear measurements, as well as the observed yield like behavior, implies that the formation of a percolating nanoclay network is the origin of the enhanced viscoelasticity in these composites.

SYNTHESIS OF POLY(METHYL METHACRYLATE)—CLAY NANOCOMPOSITES

Poly(methyl methacrylate)/clay nanocomposites were synthesized via in situ free radical polymerization of methyl methacrylate (MMA) in the presence of functionalized clay. Montmoril-lonite (MMT), a smectic type of clay, was treated with a commercial cationic surfactant, benzalkonium chloride (BAC), and a synthesized zwitterionic surfactant, octadecyldimethyl betaine (CI8DMB) Functionalized MMT was prepared via an ion exchange between Na,ions in the clay and the surfactant cations in aqueous medium. The intercalation of the surfactant in the clay galleries was determined using X-ray diffraction (XRD). The interlayer spacing for C18DMB was 2.03nm, higher than 1.86nm observed for BAC. This is due to longer chain length of C18DMB. Both organophilic clays formed a viscous gel when dispersed in the monomer, MMA. Poly(methyl methacrylate) (PMMA) nanocomposites were obtained by polymerizing the dispersions. XRD and transmission electron microscopy (TEM) indicate predominant exfoliation of the silicate layers in the polymer matrix for MMT treated with C18DMB, and partial exfoliation for MMT treated with BAC

Anaerobic degradation and toxicity of commercial cationic surfactants in anaerobic screening tests

Anaerobic biodegradability and toxicity on anaerobic bacteria of di(hydrogenated tallow) dimethyl ammonium chloride (DHTDMAC) and two esterquats have been investigated. A batch test system containing municipal digester solids as a source of anaerobic bacteria, based on the method proposed by the ECETOC, has been applied. To evaluate the potential toxicity of such surfactants on anaerobic sludge, a co-substrate, an easily biodegradable compound in anaerobic conditions, has been added to the samples to test and the effects on biogas production have been determined. For the esterquats studied high biodegradation levels were obtained and no toxic effects on anaerobic bacteria were observed even at the highest concentrations tested, 100 and 200 mg C/l, respectively. On the contrary, DHTDMAC was not degradated at the same test conditions. However, no inhibitory effects on the biogas production were detected for this surfactant at concentrations <100 mg C/l.

Micellar size of drag reducing cationic surfactants

Dynamic light scattering was employed to determine the effects of surfactant nature, concentration and counterion ratios, and shear on the hydrodynamic radii of micelles of commercial cationic surfactants which are powerful drag reducers in turbulent flow at high temperatures. Such surfactants are potentially useful for reducing pumping energy losses in district heating and cooling systems.