Gemini Quaternary Ammonium Research Articles

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.

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 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.

Application Properties of Gemini Quaternary Ammonium Salt with Quadra‐cationic Sites and Sodium Fatty Alcohol Polyoxyethylene Ether Carboxylate Mixed Systems

AbstractThe application properties such as foam property, electrolyte tolerance, antibacterial activity and antistatic performance of the mixed systems of a novel Gemini quaternary ammonium salt with quadra‐cationic sites (TC‐GS) and sodium fatty alcohol polyoxyethylene ether carboxylate (AE9CNa) at various molar fraction of TC‐GS (αTC‐GS), were investigated systematically. Results show that TC‐GS/AE9CNa mixed systems with different ratios form a homogeneous and transparent solution, which exhibits excellent foam stability and antibacterial activity. The foam volume of the mixed system remains nearly constant from 400 s to 1000 s, and even when TC‐GS is 10 mg/L in the mixed systems, the antibacterial rates against Escherichia coli (E. coli) and Staphylococcus aureus (S. aureus) for 2 min. are all exceeded 99 %. The mixed systems of TC‐GS/AE9CNa at various αTC‐GS also demonstrate the superior electrolyte tolerance, their maximum tolerance of NaCl, CaCl2 and MgCl2 is severally beyond 270 g/L, 180 g/L and 180 g/L. In addition, both TC‐GS solution and the mixed systems have good antistatic properties, which can reduce the surface resistance of polyester fabric to ≤1010 Ω.

Anti-adhesive, anti-biofilm and fungicidal action of newly synthesized gemini quaternary ammonium salts

Newly synthesized gemini quaternary ammonium salts (QAS) with different counterions (bromide, hydrogen chloride, methylcarbonate, acetate, lactate), chain lengths (C12, C14, C16) and methylene linker (3xCH2) were tested. Dihydrochlorides and dibromides with 12 carbon atoms in hydrophobic chains were characterized by the highest biological activity against planktonic forms of yeast and yeast-like fungi. The tested gemini surfactants also inhibited the production of filaments by C. albicans. Moreover, they reduced the adhesion of C. albicans cells to the surfaces of stainless steel, silicone and glass, and slightly to polystyrene. In particular, the gemini compounds with 16-carbon alkyl chains were most effective against biofilms. It was also found that the tested surfactants were not cytotoxic to yeast cells. Moreover, dimethylcarbonate (2xC12MeCO3G3) did not cause hemolysis of sheep erythrocytes. Dihydrochlorides, dilactate and diacetate showed no mutagenic potential.

Real-time monitoring of bacterial inactivating process of tailored bactericidal and antifouling cotton fabric with preserving its physicochemical properties and biocompatibility

Microorganisms present on cotton fabric (CF) significantly affect its wearing comfort and pose potential threats to human health. This is mainly attributed to the porous and hygroscopic nature of CF, which easily adsorbs proteins, oily substances, and mineral salts, creating a favorable environment for microorganism proliferations. The bacteria firmly adhered to CF are difficult to remove by conventional washing, resulting in persistent stains. Furthermore, the mechanisms underlying bacterial interaction with fibers and bacterial inactivation remain to be fully understood. Herein, we synthetized reactive Gemini quaternary ammonium salt (CGQ) and sulfopropylbetaine (CGB) to covalently bind onto CF, thereby engineering a customized antimicrobial and antifouling CF while preserving its physicochemical properties. Real-time monitoring of the bacterial inactivation process was also performed. The antimicrobial efficacy of CF finished with CGQ and CGQ/CGB, employing only 5.0 mg/mL antimicrobial concentration, surpassed 95 % against Escherichia coli and 99 % against Staphylococcus aureus after 50 washes. The loosely adhered bacteria on CGQ/CGB-finished CF can be easily eliminated through conventional washing, resulting in an enduring antimicrobial and antifouling surface. Consequently, we have developed a straightforward strategy for the large-scale production of superior antimicrobial and antifouling CF, presenting a versatile solution with wide applications. Additionally, this method offers an efficient strategy for real-time monitoring of the microorganism inactivation process.

Interaction, Surface Activity, and Application of Mixed Systems of Alcohol Ether Sulfate Anionic Surfactants with Multiple Ethylene Oxide Groups and Gemini Quaternary Ammonium Surfactant.

The surface activities and application properties for the mixtures of cationic surfactants tetramethylene-1,4-bis[N,N-bis(hydroxypropyl)-hexa/decyloxypropylammonium] bromide (GC10-P) and tetramethylene-1,4-bis[N,N-bis(hydroxyethyl)-hexa/decyloxypropylammonium] bromide (GC10-E) and anionic surfactant isomeric sodium fatty alcohol ether sulfates (iso-AE9S) were investigated using both the tensiometry and the conductometry. The interaction parameters and thermodynamic micellization parameters of GC10-P/iso-AE9S and GC10-E/iso-AE9S mixtures were evaluated by Clint-Rubingh and Motomura theoretical models. When the mole fraction of α1 for GC10-P/iso-AE9S mixed system was 0.2, the critical micelle concentration (CMC) reached a minimum of 1.61 × 10-4 mol/L, and the minimum critical micelle concentration of the GC10-E/iso-AE9S mixed system is 2.67 × 10-5 mol/L at α1 = 0.6. The CMC value of the mixed system is 1-2 orders of magnitude lower than that of any single component. The results indicate that the synergistic effects of the investigated mixed systems (evaluated by βm) are in order of GC10-P/iso-AE9S < GC10-E/iso-AE9S, with maximum βm values of -17.98 and -9.78, respectively. The change in zeta potential indicates that the poly(ethylene oxide) chain has weakened the charge density of the hydrophilic headgroup of the anionic surfactant. The interfacial tension at the oil-water interface in the mixed system of anionic/cationic surfactants is lower than that of any single component, exhibiting a higher interfacial activity. The mixed system exhibits a decreased contact angle and superior wetting ability over any single component, and it also enhances foam performance, emulsification performance, and degreasing performance.

Investigation on foam properties of Gemini quaternary ammonium salt containing hydroxyl hydrophilic headgroup

Four Gemini quaternary ammonium salts, tetramethylene-1,4- bis [N, N-bis(hydroxypropyl)-hexa/decyloxypropylammonium] bromide (GC6/10-P) and tetramethylene-1,4-bis [N, N-bis(hydroxyethyl)-hexa/decyloxypropylammonium] bromide (GC6/10-E) were synthesized by two-step reactions. This study analyzes the foam properties, including foamability, foam stability, and foam size distribution, of GC6/10-P and GC6/10-E using the Foamscan method. The influence of surfactant concentration and gas flow rate on the properties of Gemini quaternary ammonium salt foam was also studied. Additionally, the relationship between surfactant structure and foam morphology in aqueous solutions was discussed. The results show that all four types of Gemini quaternary ammonium salt surfactants are low-foaming surfactants. The foam capacity (FC) sequence is as follows: GC10-E > GC10-P > GC6-E > GC6-P. The foamability and foam stability are enhanced with increasing surfactant concentration, which increases the adsorbed quantity of surfactant molecules at the air-water interface. The foam produced by GC6-P/E systems is the most unstable; the foam behaviors show faster Ostwald ripening and drainage process in aqueous system. It seems that 150–200 mL/min is an ideal air intake speed. The presence of hydroxyl in the molecular structure enhances the formation of hydrogen bonding between surfactants and water molecules, leading to greater molecular compactness. The results indicate that the foaming behavior of hydroxyl Gemini quaternary ammonium salts can be correlated with concentration and alkyl chains. Foamscan are proposed to research the foaming and foam stability behavior and provide a useful guide for evaluating the foamability of cationic surfactants-based systems, especially in the development of environmentally friendly foam systems suitable for low-foaming products.

Quaternary ammonium salts for water treatment with balanced rate of sterilization and degradation

The growing number of infections caused by drug-resistant bacteria which arise from the overuse of antibiotics has severely affected the normal operation of human society. The high antibacterial activity of QAS makes it promising as an alternative to antibiotics, but it suffers from secondary pollution due to its non-degradation. Here we have synthesized a class of gemini quaternary ammonium salts (GQAS) with different carbon chain lengths containing ester groups by using facile methylation reaction. Quaternary ammonium groups contribute to insert negatively charged bacterial membranes, resulting in membrane damage and bacteria death. Compared with conventional single-chain QAS, except for the more efficient antibacterial efficiency attribute to the presence of the second carbon chain, GQAS with alterable antibacterial properties can minimize the possibility of bacterial resistance and reduce the accumulation of GQAS in the environment through the introduction of degradable ester groups. GQAS is completely superior to the commercial bactericide benzalkonium chloride (BAC) in both antibacterial activity and degrade performance, which can be used as a more environmentally friendly bactericide.

Rheology of high-temperature resistant fracturing fluids formed by VES, acids and oxidants for enhancing CO2 injection in deep coal seams

To address the low efficiency of CO2 injection into deep coal seams due to coal adsorption-induced swelling and low permeability, this study proposes the use of a CO2 injection enhancement fracturing fluid (IEFF) to increase injection efficiency, which is composed of viscoelastic surfactant (quaternary ammonium Gemini surfactant, 18-3-18), organic acids (acetic acid, C2H4O2) and oxidants (hydrogen peroxide, H2O2). The rheology and micelle morphology of the IEFF were investigated in terms of temperature and substance ratios. In addition, comparative study was conducted with monomeric surfactants (STAB). The results demonstrated that compared to STAB, 18-3-18 exhibited a two orders of magnitude lower critical micelle concentration (CMC), a lower surface tension (γCMC), and formed a system with favorable rheology at lower concentrations. Moreover, the viscosity of the IEFFs increased as the substance ratio of C2H4O2 to H2O2 decreased. Inflection points in the IEFFs were observed at 313.15 K, 323.15 K, and 333.15 K, where the viscosity exceeded 25 mPa·s. At 323.15 K, a shear rate of 170 s−1, and a substance ratio of 1:1.5, the IEFF reached its maximum viscosity of 40.390 mPa·s, with a micelle size of 109.56 nm, and the intertwined wormlike micelles formed a robust network structure. The results can provide a reference for optimizing fracturing fluid and promoting the efficiency of CO2 injection into deep coal seams.

Gemini Quaternary Ammonium Surfactants with Different Counterions-modified Montmorillonite for Efficient Removal of Methyl Orange.

Organic Na-montmorillonite (OMt-12-2-12·2Y - , Y=CH 3 CO 3 - , C 6 H 5 COO - and Br - ) modified by a series of Gemini quaternary ammonium surfactants with different counterions was prepared for enhancing the adsorption capacity of methyl orange. Compared with the initial adsorption capacity of 5.251 mg/g of Na-Mt, the adsorption effect of OMts under the optimal conditions increased by about 31~34 times. The adsorption isotherms and kinetics of all adsorption processes were respectively described by Langmuir and pseudo-second-order models. The structure, hydrophobicity and hydration of the counterions, as well as the affinity of the counterions with the long aliphatic chains, had a certain influence on the adsorption performance of OMts for methyl orange.

The influence of hydrogen bonding on the structure of organic-inorganic hybrid catalysts and its application in the solvent-free epoxidation of α-olefins.

In this study, two types of catalysts were prepared by the combination of gemini quaternary ammonium salt with two distinct species of phosphotungstic acid. Catalysts prepared by the Wells-Dawson type of phosphotungstic acid and Keggin-type phosphotungstic acid both exhibited dual-phase catalytic behavior, demonstrating both heterogeneous and homogeneous catalytic activities. In comparison to the catalyst prepared by the Keggin-type phosphotungstic acid, due to the higher size of Wells-Dawson type of phosphotungstic acid, hydrogen bonding could not effectively affect the catalyst prepared by H6P2W18O62. Subsequently, the influential factors on the catalytic reaction were investigated. Through the utilization of techniques such as XPS, FT-IR, Raman spectra and other characterization methods, two distinct structure and reaction mechanisms for these catalysts were elucidated under the influence of hydrogen bonding.

Study on the epoxidation of chain olefins using biquaternary ammonium phosphotungstic acid phase transfer catalysts under no-solvent condition.

In this study, we have developed a novel catalyst synthesized by phosphotungstic acid and a gemini quaternary ammonium cation salt. This quaternary ammonium salt not only reduces the interfacial tension between olefins and hydrogen peroxide but also forms a notably stable structure with phosphotungstic acid. Dodecene was successfully epoxidized to epoxy dodecane with a selectivity of 82.9 %. The impact of initial conditions was systematically investigated such as molar ratio, temperature, reaction time, and catalyst dosage on the catalytic performance. Characterization of the catalyst morphology was performed by SEM, TEM and SAXS. Raman spectra, FT-IR and XPS spectra were employed to perform the catalyst transformation during the epoxidation reaction. This catalytic mechanism study could provide the industrial application in the epoxidation of long-chain olefins.

Separation of avibactam by gemini quaternary ammonium salt: Extraction, precipitation, and application in large-scale production

β-lactamase inhibitors have important clinical significance to restore the antibacterial effect of antibiotics. Non-β-lactam β-lactamase inhibitor represented by avibactam contained a sulfonic acid group, which posed a considerable challenge to separation and purification. To separate avibactam, eight gemini quaternary ammonium salts were developed for extraction, and the extraction conditions were investigated and optimized. Notably, some gemini quaternary ammonium salts can directly precipitate avibactam in aqueous solution with the excellent yield and purity. The probable mechanism of precipitation was studied by critical micelle concentration, transmission electron microscopy, and nuclear magnetic resonance assays. The precipitation process of gemini quaternary ammonium salt N,N,N,N′,N′,N′-hexabutylbutanediammonium dibromide was successfully applied in separation and purification of a 2 kg avibactam production, showing unique efficient and green advantages. Our research offered an effective and scale-up approach to separation and purification of β-lactamase inhibitor containing sulfonic acid group.

Effect of Quaternary Ammonium Gemini Surfactant Solution on the Rate Constant of the Ninhydrin–Lysine Reaction

Effect of Quaternary Ammonium Gemini Surfactant Solution on the Rate Constant of the Ninhydrin–Lysine Reaction

Preparation and characterization of a self-matting waterborne polyurethane with antibacterial function

Self-matting waterborne polyurethane (WPU) with rough surface is often accompanied by poor antibacterial property, which greatly limits its service life. Here, a gemini quaternary ammonium (GQM) with hydrophilic and antimicrobial properties was designed and synthesized. 1,3,5-tris (2-hydroxyethyl) hexahydro-1,3,5-Triazine (TNO) was used as a crosslinking agent, and GQM was selected as chain extender to prepare antibacterial and self-matting WPU resin. The effects of TNO and GQM on the morphology, particle size, gloss, antibacterial rate, and hydrophilicity of WPU were investigated. The results showed that the introduction of TNO and GQM significantly enhanced the self-matting effect and antibacterial activity of WPU. When the contents of TNO and GQM were 1.2 wt% and 4 wt%, the average particle size of emulsion was 6.53 μm, the gloss of coating was 11.05 GU. It is also significant to be noted that the antibacterial rates of S. aureus and E. coli were 95.69 % and 95.18 %, respectively. This prepared WPU was endowed with self-matting and antibacterial properties simultaneously. This finding can provide a novel insight into the research of antibacterial polymers and antiglare coatings.

Self-Aggregation, Antimicrobial Activity and Cytotoxicity of Ester-Bonded Gemini Quaternary Ammonium Salts: The Role of the Spacer.

Five ester-bonded gemini quaternary ammonium surfactants C12-En-C12 (n = 2, 4, 6), with a flexible spacer group, and C12-Bm-C12 (m = 1, 2), with rigid benzene spacers, were synthesized via a two-step reaction and analyzed. Furthermore, the effects of the spacer structure, spacer length and polymerization degree on the self-aggregation, antimicrobial activity and cytotoxicity of C12-En-C12 and C12-Bm-C12 and their corresponding monomer N-dodecyl-N,N,N-trimethyl ammonium chloride DTAC were investigated. The results showed that C12-En-C12 and C12-Bm-C12 had markedly lower critical micellar concentration (CMC) values and lower surface tension than DTAC. Moreover, the CMC values of C12-En-C12 and C12-Bm-C12 decreased with increasing spacer length. In the case of equivalent chain length, the rigidity and steric hindrance of phenylene and 1,4-benzenediyl resulted in larger CMC values for C12-Bm-C12 than for C12-En-C12. The antibacterial ability of C12-En-C12 and C12-Bm-C12 was assessed using Escherichia coli (E. coli) and Staphylococcus albus (S. aureus) based on minimum inhibitory concentrations (MICs). Furthermore, C12-En-C12 and C12-Bm-C12 exhibited higher antimicrobial activity than DTAC and had stronger function toward S. aureus than E. coli. The antimicrobial activity was enhanced by increasing the spacer chain length and decreased with the increased rigidity of the spacers. The cytotoxic effects of C12-En-C12 and C12-Bm-C12 in cultured Hela cells were evaluated by the standard CCK8 method based on half-maximal inhibitory concentration (IC50). The cytotoxicity of C12-En-C12 and C12-Bm-C12 was significantly lower than alkanediyl-α,ω-bis(dimethyldodecylammonium) bromide surfactants and DTAC. The spacer structure and the spacer length could induce significant cytotoxic effects on Hela cells. These findings indicate that the five ester-bonded GQASs have stronger antibacterial activity and lower toxicity profile, and thus can be used in the pharmaceutical industry.

A new avibactam Gemini quaternary ammonium salt: synthesis, self-assembly, vibrational spectra, crystal structures and DFT calculations

Avibactam ([AV]), a non-β-lactam β-lactamase inhibitor, contains a sulfonic acid group, which making separation and purification extremely difficult. The ability of the gemini quaternary ammonium salt N,N,N,N’,N’,N’-hexabutylbutanediammonium dibromide [444][Br]2 to precipitate [AV] from aqueous solutions resulted in the successful synthesis of a new avibactam gemini quaternary ammonium salt [444][AV]2. To understand the self-assembly, the transmission electron microscope (TEM) and spectra of [444] cations and [AV] anions in aqueous solution were investigated. By using a slow evaporation technique, the [444][AV]2 complex single crystal was produced from a water solvent. The title crystal structure conformation was done by single crystal X-ray diffraction (SCXRD) technique, and its belongs to the P-1 space group with the triclinic system. The thermal stability of [444][AV]2 has been investigated by TG/DSC studies, and its experimental vibrational bands (FT-IR and Raman) have been studied and assigned. The stability test indicated that [444][AV]2 exhibits outstanding physical stability under long-term and accelerated conditions. According to DFT calculations, electrostatic potential and Mulliken charges showed that [444] cations were readily adsorbed on the negatively charged [AV] anions surface sites through electrostatic attraction, and the existence of inter-molecular interactions was assessed by Hirshfeld surface of [444][AV]2 single crystal.

O/D emulsions stabilized by quaternary ammonium gemini surfactants together with alumina nanoparticles

AbstractOil‐in‐dispersion (O/D) emulsions are the focus in many fields due to their new microstructures and new functions. Herein, O/D emulsions were successfully prepared using series of cationic gemini surfactants 12‐s‐12 (s = 2, 3, and 6) and alumina nanoparticles. The microstructures and type of emulsions were identified using optical microscopy, zeta potential and contact angle methods. Gemini surfactants with two head groups carry more charges than that of conventional surfactants when adsorbed at the oil–water interface. The O/D emulsions can be stabilized at lower surfactant concentrations compared with the conventional single‐headed surfactants. In the presence of 0.1 wt% alumina nanoparticles, gemini surfactants 12‐s‐12 (s = 2, 3, and 6) can stabilize emulsions at the concentration of 3 × 10−4 mM (1.84 × 10−5 wt%), 6 × 10−4 mM (3.76 × 10−5 wt%) and 1 × 10−3 mM (6.68 × 10−5 wt%), respectively. Addition of excessive organic salts such as sodium salicylate and sodium p‐methylbenzenesulfonate shielded the head group charges of gemini surfactants, leading to gemini surfactants to behave as nonionic surfactants Adsorption of surfactants at the alumina nanoparticles occurred, resulting in the transformation from the O/D emulsions to Pickering emulsions. This work shows the advantages of preparing O/D emulsions using gemini surfactants and also provides a new methods of emulsion type transformations by adding excessive oppositely charged organic salts.

Organo-Montmorillonite Modified by Gemini Quaternary Ammonium Surfactants with Different Counterions for Adsorption toward Phenol

The discharge of industrial phenol pollutants causes great harm to the natural environment and human health. In this study, phenol removal from water was studied via the adsorption of Na-montmorillonite (Na-Mt) modified by a series of Gemini quaternary ammonium surfactants with different counterions [(C11H23CONH(CH2)2N+ (CH3)2(CH2)2 N+(CH3)2 (CH2)2NHCOC11H23·2Y-, Y = CH3CO3-, C6H5COO- and Br-, 12-2-12·2Y-]. The results of the phenol adsorption indicated that MMt-12-2-12·2Br-, MMt-12-2-12·2CH3CO3- and MMt-12-2-12·2C6H5COO- reached the optimum adsorption capacity, which was 115.110 mg/g, 100.834 mg/g and 99.985 mg/g, respectively, under the conditions of the saturated intercalation concentration at 2.0 times that of the cation exchange capacity (CEC) of the original Na-Mt, 0.04 g of adsorbent and a pH = 10. The adsorption kinetics of all adsorption processes were in good agreement with the pseudo-second-order kinetics model, and the adsorption isotherm was better modeled by Freundlich isotherm. Thermodynamic parameters revealed that the adsorption of phenol was a physical, spontaneous and exothermic process. The results also showed that the counterions of the surfactant had a certain influence on the adsorption performance of MMt for phenol, especially the rigid structure, hydrophobicity, and hydration of the counterions.