Amido-Amine-Based Cationic Gemini Surfactants: Thermal and Interfacial Properties and Interactions with Cationic Polyacrylamide

Experimental studies were conducted to investigate thermal and interfacial properties of two in‐house synthesized amido‐amine‐based cationic gemini surfactants namely: dodecanoic acid [3‐({4‐[(3‐dodecanoylamino‐propyl)‐dimethyl‐amino]‐butyl}‐dimethyl‐amino)‐propyl]‐amide dibromide ( 12‐4‐12 ) and dodecanoic acid [3‐({6‐[(3‐dodecanoylamino‐propyl)‐dimethyl‐amino]‐hexyl}‐dimethyl‐amino)‐propyl]‐amide dibromide ( 12‐6‐12 ). Thermogravimetric analysis showed the excellent thermal stability of surfactants and no structural degradation was observed at temperatures up to 250 °C. The long‐term thermal stability of the surfactants was investigated with the aid of spectroscopic techniques such as nuclear magnetic resonance (NMR (¹H and ¹³C) and Fourier transform infrared (FTIR) spectroscopy. Both surfactants were found to be thermally stable, and no changes in structure were observed after aging for 10 days at 90 °C. The interfacial tension of the surfactants was measured at three different temperatures (30, 60, and 80 °C), and the results showed a decrease in interfacial tension with increasing temperature and increasing spacer length of the surfactants. Rheological measurements were used to assess the interactions between the cationic gemini surfactant and cationic polyacrylamide. The addition of cationic surfactant reduced the viscosity and storage modulus of the polymer at low shear rate and frequency due to surfactant–polymer interactions and charge screening. The investigated surfactant–polymer system has great potential in high‐temperature carbonate reservoirs, where conventional anionic surfactants are not recommended due to high adsorption.     

The Effects of Amide Bonds and Aromatic Rings on the Surface Properties and Antimicrobial Activity of Cationic Surfactants

The cationic surfactants containing aromatic rings and amide bonds, N,N-dimethyl-N-dodecyl-2-pyrimidinylcarbamoylmethyl ammonium chloride ( a ), N,N-dimethyl-N-dodecyl-2-thiazolylcarbamoylmethyl ammonium chloride ( b ), and N,N-dimethyl-N-dodecyl-phenylcarbamoylmethyl ammonium chloride ( c ), were synthesized and characterized. The surface tension and conductivity values were employed to investigate the absorption and micellization behavior of the three cationic surfactants. The results showed that the synthesized surfactants have shown a low critical micelle concentration (CMC) and a high adsorption efficiency (pC₂₀) compared with the traditional cationic surfactant of N,N-dimethyl-N-dodecyl-N-benzyl ammonium chloride ( BAC-12 ). The aromatic rings of the a , b , and c molecular structures were analyzed using the ¹H NMR spectra for electrostatic repulsion effects between hydrophilic headgroups. The size distribution of the micelles was derived using dynamic light scattering (DLS) techniques. In addition, the foaming ability of a , b , c , and BAC-12 was investigated and the antimicrobial activity of a , b , c , and BAC-12 against Escherichia coli, Staphylococcus aureus, and Bacillus subtilis was examined. The effects of amide bonds and aromatic rings on the surface properties and antimicrobial activity of a , b , and c were analyzed and compared with BAC-12 of the same alkyl chain length. The synthesized surfactants exhibited a high surface ability and better antibacterial activity compared with BAC-12 .     

Synthesis,Characterization, and Micellization Behavior of Cationic Surfactants: n-Alkyl-3-Methylpyridinium Bromides and Their Drug Interaction Study by UV–Visible Spectroscopy and Conductometry

The synthesis of new cationic surfactants i.e., n-hexyl-3-methylpyridium bromide ( a ) and n-octyl-3-methylpyridium bromide ( b ), and their characterization using multinuclear nuclear magnetic resonance spectroscopy (NMR) (¹H, ¹³C) and Fourier-transform infrared spectroscopy (FT-IR) spectroscopic techniques were reported. The micellization behavior of the synthesized surfactants was studied using conductometry and ultraviolet–Visible spectroscopy. The critical micelle concentration (CMC) of compounds a and b was found to be 0.41 and 0.35 m mol L⁻¹, respectively. The effect of temperature on the CMC of these compounds was examined in the range of 298–318 K and thermodynamic parameters (ΔG, ΔH, and ΔS) of the micellization process were calculated. The antibacterial study of the synthesized surfactants revealed their strong activity against different bacterial strains. Moreover, the interaction of drugs i.e., flurbiprofen and ketoprofen, with the synthesized surfactants was investigated for gaining insights into the role of micelles as drug-delivery devices. Drug–surfactant interactions were also confirmed via a conductometric method.     

Synthesis, Surface Active Properties of Novel Gemini Surfactants with Amide Groups and Rigid Spacers

A series of novel cationic gemini surfactants, bis-(N-(3-alkylamido-propyl)-N,N-dimethyl)-p-phenylenediammonium dichloride, were synthesized. The structures of the gemini surfactants were characterized by IR, ¹H NMR and ¹³C NMR. The Krafft temperatures of surfactants were determined through conductivity, the surface active properties in aqueous solution were studied at various temperatures by surface tension and conductivity. The thermodynamic functions of micellization process of the surfactants were also calculated by conductivity. The Krafft temperatures of the surfactants were 12, 13 and 28 °C. The values of CMC and Γ _max decreased with increasing the length of hydrophobic chains, but the values of CMC and α increased with increasing temperature. The process of micellization is a spontaneous, exothermic and entropy-driven process.     

Surface Parameters and Biological Activity of <Emphasis Type="Italic">N</Emphasis>-(3-(Dimethyl Benzyl Ammonio) Propyl) Alkanamide Chloride Cationic Surfactants

Three cationic surfactants containing amide groups were prepared by quaternization of dimethylaminopropylamine with benzyl chloride. FTIR and ¹H-NMR spectroscopy were used to confirm the chemical structure of the prepared cationic surfactants. The surface parameters were estimated using surface tension measurements at three different temperatures. The prepared cationic surfactant showed a lower CMC than conventional cationic surfactants. Thermodynamic parameters of adsorption and micellization depend mainly of alkyl chain length and temperature. The adsorption process is more favorable than micellization. The biological activity of the three surfactants was estimated using inhibition zone showing that amidoamine cationic surfactants have good activity and the surfactants C12Bn is the most effective one.     

Friction dynamics of human hair treated with water or cationic surfactant aqueous solution

Cationic surfactants are adsorbed on the surface of human hair and exhibit a lubricating effect. Here, we evaluated the friction when the hair treated with water or 1 wt% cationic surfactant (cetyltrimethylammonium bromide) aqueous solution was rubbed by a contact probe equipped in a sinusoidal motion friction evaluation system. Because of the rough structure of the cuticle on the human hair surface, an oscillatory phenomenon with a frequency of 50–70 Hz was observed when untreated hair was rubbed with a contact probe. On the other hand, the oscillatory phenomenon was not observed when the hair contained a large amount of water because stick–slip phenomena were inhibited on the soft, swollen hair surface. Furthermore, the change in kinetic friction coefficient and delay time, which is a normalized value of the time difference between the reaction of the friction force to accelerated motion, from untreated hair, Δμ_k and Δδ, was almost zero. However, we found a large difference in Δμ_k and Δδ for the hair treated with cationic surfactant aqueous solution. The treatment with cationic surfactant reduced both friction parameters, Δμ_k and Δδ, indicating that the treatment induced not only the frictional force but also the profile at the beginning of frictional sliding. The significant lubrication is due to cationic surfactant adsorption on the hair surface. These data imply that the smoothness of hair treated with a cationic surfactant is related to a reduction in friction coefficient and delay time δ.     

Synthesis and antimicrobial properties of a guanidine‐based oligomer grafted with a reactive cationic surfactant through Michael addition

A guanidine‐based oligomer grafted with a reactive cationic surfactant was designed and synthesized through Michael addition in an attempt to combine its antibacterial and emulsification properties. This was also an excellent and efficient strategy for preparing more kinds of guanidine derivatives. Fourier transform infrared spectroscopy, ¹H‐NMR, and ¹³C‐NMR showed that the guanidine‐based oligomer grafted with reactive cationic surfactant was synthesized successfully. The antimicrobial activity and antimicrobial mechanism were investigated with several approaches. The antimicrobial activity results indicated that the introduction of a cationic surfactant into the guanidine‐based oligomer effectively raised the antimicrobial activity and showed a synergistic effect. The UV absorption at 260 nm was used to detect the dynamic antimicrobial process of the modified guanidine oligomer. Further, the results of scanning electron microscopy and atomic force microscopy implied that the antimicrobial mechanism of the modified guanidine oligomer changed the permeability of the cell membrane of the bacteria and caused the leakage of intracellular components of the Escherichia coli cells. © 2013 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 130: 3489–3497, 2013     

Enhanced oil recovery from high‐salinity reservoirs by cationic gemini surfactants

In order to enhance oil recovery from high‐salinity reservoirs, a series of cationic gemini surfactants with different hydrophobic tails were synthesized. The surfactants were characterized by elemental analysis, infrared spectroscopy, mass spectrometry, and ¹H‐NMR. According to the requirements of surfactants used in enhanced oil recovery technology, physicochemical properties including surface tension, critical micelle concentration (CMC), contact angle, oil/water interfacial tension, and compatibility with formation water were fully studied. All cationic gemini surfactants have significant impact on the wettability of the oil‐wet surface, and the contact angle decreased remarkably from 98° to 33° after adding the gemini surfactant BA‐14. Under the condition of solution salinity of 65,430 mg/L, the cationic gemini surfactant BA‐14 reduces the interfacial tension to 10^?3 mN/m. Other related tests, including salt tolerance, adsorption, and flooding experiments, have been done. The concentration of 0.1% BA‐14 remains transparent with 120 g/L salinity at 50 °C. The adsorption capacity of BA‐14 is 6.3–11.5 mg/g. The gemini surfactant BA‐14 can improve the oil displacement efficiency by 11.09%. © 2017 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2018 , 135, 46086.     

Synthesis,Characterization, Surface and Biological Activity of Diquaternary Cationic Surfactants Containing Ester Linkage

Two series of diquaternary cationic surfactants designated as E9Nm and E11Nm having two different alkyl chains in their chemical structure were synthesized. The chemical structures of these surfactants were confirmed using elemental analysis, FTIR and ¹H‐NMR spectra. The surface activities of the different surfactants were determined using surface and interfacial tension at 25 °C. The surface parameters including: critical micelle concentration, effectiveness, efficiency, maximum surface excess and minimum surface area were determined. The surface activities of the cationic surfactants were correlated with their chemical structure. The surface activities of the surfactants increased with increasing the hydrophobic chain length. The adsorption and micellization tendencies of the surfactants in solution were determined using the free energies of adsorption and micellization. The synthesized surfactants were evaluated as biocides against bacteria and fungi. Biocidal activity data showed that a gradual increase in the hydrophobic chain length of the surfactant molecules gradually increases the efficiency of these surfactants as biocides.     

Synthesis and Evaluation of Novel Amido-Amine Cationic Gemini Surfactants Containing Flexible and Rigid Spacers

New amido‐amine‐based cationic gemini surfactants with flexible and rigid spacers and different hydrophobic tails were synthesized and characterized. These gemini surfactants were prepared by a modified procedure through amidation of long chain carboxylic acids using 3‐(dimethylamino)‐1‐propylamine followed by treatment with halohydrocarbons. The effect of the trans and cis conformation of the spacer double bond was investigated by means of critical micelle concentration, surface tension reduction, and thermal stability. The short‐term thermal stability of the gemini surfactants was assessed using thermogravimetric analysis (TGA) and the long‐term thermal stability was examined by a unique approach based on structure characterization techniques including NMR (¹H and ¹³C) and FTIR analysis. TGA results demonstrated excellent short‐term thermal stability since no structure degradation was observed up to 200 °C. Structural characterization revealed impressive long‐term thermal stability of the gemini surfactants with no structure decomposition after exposing them to 90 °C for 10 days. The critical micelle concentration of gemini surfactants was found to be in the range of 0.77 × 10^?4–3.61 × 10^?4 mol L^?1 and corresponding surface tension (γ_CMC) ranged from 30.34 to 38.12 mN m^?1. The surfactant with the trans conformation of spacer double bond showed better surface properties compared to the surfactant with the cis conformation of spacer double bond. Similarly, increasing surfactant tail length and spacer length resulted in decreasing CMC values. Moreover, bromide counterion showed improved surface properties compared to chloride counterion.     

NMR characterization of dihydrosterculic acid and its methyl ester

Cyclopropane FA occur in nature in the phosphoplipids of bacterial membranes, in oils containing cyclopropene FA, and in Litchi sinensis oil. Dihydrosterculic acid (2-octyl cyclopropaneoctanoic acid) and its methyl ester were selected for ¹H and ¹³C NMR analysis as compounds representative of cyclopropane FA. The 500 MHz ¹H NMR spectra acquired with CDCl₃ as solvent show two individual peaks at −0.30 and 0.60 ppm for the methylene protons of the cyclopropane ring. Assignments were made with the aid of 2D correlations. In accordance with previous literature, the upfield signal is assigned to the cis proton and the downfield signal to the trans proton. This signal of the trans proton is resolved from the peak of the two methine protons of the cyclopropane ring, which is located at 0.68 ppm. The four protons attached to the two methylene carbons α to the cyclopropane ring also show a split signal. Two of these protons, one from each methylene moiety, display a distinct shift at 1.17 ppm, and the signal of the other two protons is observed at 1.40 ppm, within the broad methylene peak. The characteristic peaks in the ¹³C spectra are also assigned.     

Retracted: Synthesis,Characterization, and Surface Activities of Polymeric Cationic Thiol Surfactants in Aqueous Medium

A series of cationic polyurethane surfactants [PQ_8-18] were synthesized by the reaction of alkyl bromoacetate (namely: octyl-, decyl-, dodecyl-, tetradecyl-, hexadecyl-, and octadecyl bromoacetate) as quaternizing agents and modified polyurethane contains tertiary amine species. Modified polyurethane was prepared by the reaction of toluene diisocyanate (TDI) and triethanol amine monomercaptoacetate. The chemical structures of the prepared surfactants were confirmed using elemental analysis, Fourier transform infrared spectroscopy (FTIR), and Proton nuclear magnetic resonance (¹H NMR) spectroscopy. The molecular weight measurements of the prepared polymers showed that the segments of each polymer contain average 10 units of the urethane-triethanol amine mercaptoacetate. The surface activities of the prepared surfactants including: surface tension (γ), effectiveness ( π_cmc), concentration at micelle formation (CMC), efficiency (Pc₂₀), maximum concentration at the interface (Γ_max), and the average area occupied by each surfactant molecule at the interface at equilibrium ( A _min) of surfactants solutions were established at 25°C. The surface tension and the critical micelle concentration values of the prepared surfactants were gradually decreased by the gradual increase of their alkyl chain length. The prepared cationic surfactants showed efficient activity as inhibitors for dissolution of carbon steel in an acidic medium and also as a biocide against the growth of bacteria, fungi, and yeast.     

Extraction of Rare Earth Metals Using Liquid Surfactant Membranes Prepared by a Synthesized Surfactant

Abstract

Three surfactants, l-glutamic acid dioleyl ester ribitol (nonionic, 2C ₁₈Δ⁹ GE), l-glutamic acid dioleyl ester quaternary ammonium chloride (cationic, 2C ₁₈Δ⁹ GEC ₂ QA), and dioleyl dimethyl quaternary ammonium chloride (cationic, 2C ₁₈Δ⁹ QA) were synthesized for potential use in liquid membrane operations. These surfactants have strongly hydrophobic, twin oleyl chains as the hydrophobic moiety. Using the synthesized surfactants, extraction of rare earth metals was carried out by liquid surfactant membranes in a stirred tank. The extraction behavior of 12 kinds of rare earth metals was systematically studied with 2-ethylhexyl phosphoric acid mono-2-ethylhexyl ester (commercial name: PC-88A) as a carrier. Different surfactants having an identical hydrophobic moiety can have significantly different behaviors in rare earth extractions by liquid surfactant membranes, where extraction efficiency appears to be governed by the nature of the interfacial microenvironment between oil and water. An interfacial reaction model which takes into account the adsorption of a surfactant at the interface has been proposed to evaluate the permeation rate of rare earth metals by liquid surfactant membranes. It was found that a cationic surfactant strongly enhances the extraction rate of rare earth metals compared with the conventional surfactant, Span 80. The cationic surfactant 2C ₁₈Δ⁹ GEC ₂ QA appears to be one of the best surfactants currently available for rare earth extraction by liquid surfactant membranes.     

A Zwitterionic Surfactant Bearing Unsaturated Tail for Enhanced Oil Recovery in High‐Temperature High‐Salinity Reservoirs

High‐temperature/high‐salinity (HTHS) reservoirs contain a significant fraction of the world's remaining oil in place and are potential candidates for enhanced oil recovery (EOR). Selection of suitable surfactants for such reservoirs is a challenging task. In this work, two synthesized zwitterionic surfactants bearing a saturated and an unsaturated tail, namely 3‐(N‐stearamidopropyl‐N,N‐dimethyl ammonium) propanesulfonate and 3‐(N‐oleamidopropyl‐N,N‐dimethyl ammonium) propanesulfonate, respectively, were evaluated. The surfactant with the unsaturated tail showed excellent solubility in synthetic seawater (57,643 ppm) and in formation brine (213,734 ppm). However, the unsaturated surfactant with a saturated tail showed poor solubility, and therefore it was not evaluated further. The thermal stability of the synthesized unsaturated surfactant solution in seawater was evaluated by heating the solution at 90 °C in a sealed aging tube for 2 weeks. The thermal stability of the unsaturated surfactant was confirmed by FTIR and NMR analysis of the aged samples at such harsh conditions. The critical micelle concentration (CMC) of the synthesized unsaturated surfactant in seawater was 1.02 × 10^?4 mol L^?1, while the surface tension at CMC was 30 mN m^?1. The synthesized unsaturated surfactant was able to reduce the oil–water interfacial tension to ~10^?1 mN m^?1 at different conditions. A commercial copolymer of acrylamide and 2‐acrylamido‐2‐methylpropane sulfonic acid (AM‐AMPS) was tested for EOR applications in HTHS conditions. The addition of the synthesized unsaturated surfactant to the AM‐AMPS copolymer increased the viscosity of the system. The increase in oil recovery by injecting the unsaturated surfactant solution and the surfactant–polymer mixture in solution was 8 and 21%, respectively. The excellent properties of the synthesized unsaturated surfactant show that surfactants with an unsaturated tail can be an excellent choice for HTHS reservoirs.     

Microwave-Assisted Synthesis and Properties of a Novel Cationic Gemini Surfactant with the Hydrophenanthrene Structure

A novel cationic gemini surfactant with the hydrophenanthrene structure has been synthesized from dehydroabietic acid by use of conventional thermal conditions and microwave irradiation. Its structure was confirmed by IR, ¹H NMR, and ¹³C NMR spectroscopy. It was found that microwave-assisted synthesis is an efficient means of preparation of this cationic gemini surfactant, with shorter reaction times and higher yields. The title compound had high surface activity. The CMC was 3.1 × 10⁻⁵ mol L⁻¹, γ _CMC was 26.3 mN m⁻¹, and emulsifying power (with benzene) reached five days. Comparison of this gemini surfactant and its monomeric counterpart proved the gemini surfactant was more surface active.

Biological Behaviors of Guanidine-Based Cationic Surfactants

The biological properties of novel guanidine‐based cationic surfactant including mono‐alkylguanidine (CnG), N,N,N′‐dimethyl alkylguanidine (CnMG), dicephalic guanidine surfactant (CnGQ), heterogemini guanidine surfactant (diCnGQ) were investigated. Antimicrobial activity was determined via the inhibition of cell viability of the prepared compounds, which was measured against three strains of a representative group of microorganisms. The inhibitions of cell viability were basically about 90 % at the concentration of 25 mg L^?1 to alkyl guanidium salts (CnG, CnMG), and higher than 95 % at a concentration of 10 mg L^?1 to dicephalic guanidine surfactants (CnGQ) and heterogemini guanidine surfactants (diCnGQ). The interactions of bovine serum albumin (BSA) with guanidine surfactants were investigated by fluorescence technology and the effect on BSA conformation follow the order: diC12GQ > C12GQ > C12G > C12MG. At any particular concentration, the biological activity depends on the alkyl chain length to any series of guanidine‐based cationic surfactants.     

Synthesis and Surface Properties of Polyether-Based Silicone Surfactants with Different Siloxane Groups

A series of polyether-based silicone surfactants with different hydrophobic chains (trimethylsiloxy, triethylsiloxy, and triisopropylsiloxy) were synthesized. The molecular structures were confirmed using ¹H nuclear magnetic resonance (NMR), ¹³C NMR, ²⁹Si NMR, and fourier transform infrared spectroscopy (FT-IR). The effect of the siloxane groups on the physicochemical properties, surface tension (γ), critical micelle concentration (CMC), surface tension at the CMC (γ_CMC ), adsorption efficiency (pC₂₀), surface pressure at the CMC (π_CMC ), maximum surface excess (Γ_max ), single silicone surfactant molecule at the air/water interface (A_min ), and the standard free energy of adsorption (), of the polyether-based silicone surfactants was investigated. Results indicate that the polyether-based silicone surfactants can reduce the surface tension of water to approximately 25–31 mN m⁻¹ and the surface activity of silicone surfactants is enhanced with increasing branched trimethylsiloxyl and sterically hindered siloxane groups.     

Synthesis,Surface Properties,and Antibacterial Activity of Novel Ester-Containing Cationic Silicone Surfactants and Their Utilization as Fabric-Finishing Agents

In this study, a series of cationic silicone surfactants SiQC_nCl containing ester groups and double long-chain alkyls (n = 9, 11, 13, 15, and 17) were synthesized by microwave irradiation and characterized using infrared Fourier transform (FTIR), ¹H nuclear magnetic resonance (¹H NMR), and thermogravimetric analysis (TGA). Surface activity and adsorption of these surfactants were investigated by measuring the equilibrium surface tension. The critical micelle concentration (CMC) decreased with increasing alkyl length of SiQC_nCl at 25 °C and so did the corresponding surface tension at the CMC (γ_CMC ). The aggregation behavior in aqueous solutions was also investigated systemically through transmission electron microscopy (TEM) and dynamic light scattering (DLS). Spherical or ellipsoidal-like aggregates with diameters ranging from 300 to 900 nm were observed. It is also shown that the cationic silicone surfactants exhibit certain antibacterial properties against Staphylococcus aureus but slightly poor to Escherichia coli. The morphological structure of SiQC₁₅Cl-treated cotton fabrics was observed using scanning electron microscopy (SEM), which showed that the surface became neat and smooth. What is more, the finished cotton fabrics maintained some antibacterial properties with improved softness, which may provide a more comfortable and healthy lifestyle. This work may also be helpful to the design and application of functional cationic silicone surfactants.     

Solubility of Two Disperse Dyes Derived from <Emphasis Type="Italic">N</Emphasis>-Alkyl and <Emphasis Type="Italic">N</Emphasis>-Carboxylic Acid Naphthalimides in the Presence of Gemini Cationic Surfactants

The solubility of naphthalimide-based monoazo dyes containing N-ethyl and N-ethanoic acid groups was investigated in the presence of a conventional monomeric counterpart (DTAB) and two cationic gemini surfactants (12-4-12 or 14-4-14) individually. The effective parameters on dye solubility such as temperature, time and concentration of surfactants were investigated by UV–Visible spectrophotometry. The results demonstrate that the solubility of both dyes was considerably increased at concentrations above the surfactant CMC. The wavelength for the maximum absorbance of dyes in the aqueous solution shifts toward longer wavelengths with changes in the concentration of the cationic surfactants. A kinetic study of solubilization of dyes in cationic surfactants solution showed that the rate of solubilization follows the pseudo-first-order reactions. Rates of solubilization were in the range of 0.5 × 10⁻³ to 6.8 × 10⁻³ min⁻¹ for both dyes. The disperse dye containing a carboxylic acid group (dye 2) has a higher solubility rate than the dye containing an alkyl group (dye 1). The type of surfactant has a very low effect on adsorption of dye 1 onto the polyester fibers, whereas changing the surfactant type from DTAB to 12-4-12 or 14-4-14 causes adsorption of dye 2 on polyester to decrease.     

The Impact of In‐situ Fabric Surface Energy on Dehydration of Fabrics

Reducing liquid surface tension is widely used to increase the efficiency of the centrifugal dehydration in textile wet processing. However, increasing the dehydration efficiency by decreasing fabric surface energy is seldom studied. In this work, the impact of in situ fabric surface energy on residual moisture content (RMC) of fabrics in the dehydration processes was investigated. Different types of fluorocarbon surfactants including cationic, anionic, nonionic and amphoteric were adopted as additives in this study. The liquid surface tension and RMC were efficiently decreased when fluorocarbon surfactants were used. Notably, a cationic fluorocarbon surfactant displays similar surface tension but distinct dehydration efficiency. The in situ fabric surface energy was evaluated by measuring the n‐octane contact angle on the cotton fabric surface under the surfactant solution using the captive bubble method. It was found that the cationic fluorocarbon surfactant system gave the lowest fabric surface energy, which was probably because cationic fluorocarbon surfactants are easier to adsorb onto the surface of cotton fabric to form a fluorocarbon layer. The chemical composition (¹⁹F, ¹²C and ¹⁶O) analysis of the cotton fabric surface by X‐ray photoelectron spectroscopy confirms the hypothesis.