Abstract
Gemini quaternary ammonium salts are synthesized by the one-step method which are GC-BA with a counterion of benzene sulfonate and GC-MA with a counterion of methanesulfonate. Then, the expected structure is proved by FT-IR, ESI-MS, 1H NMR, and 1H-1H COSY. Most importantly, the adsorption behavior at various interfaces and the aggregation properties in aqueous solutions are investigated. The adsorption circumstances when the equilibrium is reached at the gas/liquid interface are evaluated by surface tension (ST) tests, while the short-term kinetic process is assessed by dynamic surface tension (DST) measurements. The adsorption at the gas/liquid/solid triple-phase is characterized by the contact angle, and the adsorption at the oil/water interface is expressed by oil/water interfacial tension (ITF). Finally, the aggregation properties are illustrated by conductivity measurements. In summary, some basic theoretical data for the new Gemini quaternary ammonium salts with organic counterions can be provided.
Similar content being viewed by others
Data availability
The data that support the findings of this study are available from the corresponding author upon reasonable request.
References
Xu HJ, Wang C, Lin LL, Xu J (2019) Synthesis and properties of novel phenylenediamine Gemini surfactants. J Surfactants Deterg 22:683–690
Druvari D, Koromilas ND, Lainioti GC, Bokias G, Vasilopoulos G, Vantarakis A, Baras I, Dourala N, Kallitsis JK (2016) Polymeric quaternary ammonium-containing coatings with potential dual contact-based and release-based antimicrobial activity. ACS Appl Mater Interfaces 8:35593–35605
Wang Y, Jiang Y, Geng T, Ju H, Duan S (2019) Synthesis, surface/interfacial properties, and biological activity of amide-based Gemini cationic surfactants with hydroxyl in the spacer group. Colloids Surf A 563:1–10
Pakiet M, Kowalczyk IH, Leiva Garcia R, Akid R, Brycki BE (2018) Influence of different counterions on Gemini surfactants with polyamine platform as corrosion inhibitors for stainless steel AISI 304 in 3 M HCl. J Mol Liq 268:824–831
Lu T, Lan YR, Liu CJ, Huang JB, Wang YL (2012) Surface properties, aggregation behavior and micellization thermodynamics of a class of Gemini surfactants with ethyl ammonium headgroups. J Colloid Interface Sci 377:222–230
Zhu HL, Hu ZY, Ma XM, Wang JL, Cao DL (2016) Synthesis, surface and antimicrobial activities of cationic Gemini surfactants with semi-rigid spacers. J Surfactants Deterg 19:265–274
Wang C (2014) Different distributions of counterions in the surface layer of cationic surfactant solutions. J Dispersion Sci Technol 35:734–738
Wei X, Geng P, Han C, Guo Y, Chen X, Zhang J, Zhang Y, Sun D, Zhou S (2016) Rheological properties of viscoelastic solutions in a cationic surfactant–organic salts–water system. Ind Eng Chem Res 55:5556–5564
Yu D, Huang X, Deng M, Lin Y, Jiang L, Huang J, Wang Y (2010) Effects of inorganic and organic salts on aggregation behavior of cationic Gemini surfactants. J Phys Chem B 114:14955–14964
Wang R, Yan H, Ma W, Li Y (2016) Complex formation between cationic Gemini surfactant and sodium carboxymethylcellulose in the absence and presence of organic salt. Colloids Surf A 509:293–300
Yan HC, Li QX, Geng T, Jiang YJ (2012) Properties of the quaternary ammonium salts with novel counterions. J Surfactants Deterg 15:593–599
Ding H, Jiang Y, Wang Y, Ju H, Geng T (2021) Distributions of counterions on adsorption and aggregation behavior of Gemini quaternary ammonium salt. J Mol Liq 342:117495
Wang W, Li J, Yang X, Li P, Guo C, Li Q (2015) Synthesis and properties of a branched short-alkyl polyoxyethylene ether alcohol sulfate surfactant. J Mol Liq 212:597–604
Zhang R, Cai Y, Wang J, Zhao Z, Mao X, Peng Z (2017) A star-shaped anionic surfactant: synthesis, alkalinity resistance, interfacial tension and emulsification properties at the crude oil–water interface. J Surfactants Deterg 20:1027–1035
Ju H, Jiang Y, Geng T, Wang Y (2018) A green and easy synthesis method of catanionic surfactant ammonium benzenesulfonate and its surface properties and aggregation behaviors. J Mol Liq 264:306–313
Cao YP, Yang WG, Jiang YJ, Wang YK, Ju HB, Geng T (2021) Studies on physicochemical properties of three Gemini surfactants with different spacer groups. J Mol Liq 325:115039
Hussain SMS, Kamal MS, Murtaza M (2019) Synthesis of novel ethoxylated quaternary ammonium Gemini surfactants for enhanced oil recovery application. Energies 12
Kamal MS, Shakil Hussain SM, Fogang LT (2018) A zwitterionic surfactant bearing unsaturated tail for enhanced oil recovery in high-temperature high-salinity reservoirs. J Surfactants Deterg 21:165–174
Hussain SMS, Kamal MS, Sultan AS (2017) Amido-amine-based cationic Gemini surfactants: thermal and interfacial properties and interactions with cationic polyacrylamide. J Surfactants Deterg 20:47–55
Liu HQ, Zhou XQ, Zhang XX, Shi GY, Hu J, Liu CY, Xu BC (2018) Green synthesis, surface activity, micellar aggregation, and corrosion inhibition properties of new Gemini quaternary ammonium surfactants. J Chem Eng Data 63:1304–1315
Shaban SM, Aiad I, Fetouh HA, Maher A (2015) Amidoamine double tailed cationic surfactant based on dimethylaminopropylamine: synthesis, characterization and evaluation as biocide. J Mol Liq 212:699–707
Hua XY, Rosen MJ (1987) Dynamic surface tension of aqueous surfactant solutions: I. basic parameters. J Colloid Interface Sci 124:652–659
Liggieri L, Ravera F, Passerone A (1996) A diffusion-based approach to mixed adsorption kinetics. Colloids Surf, A 114:351–359
Domínguez-Arca V, Sabín J, Taboada P, García-Río L, Prieto G (2020) Micellization thermodynamic behavior of Gemini cationic surfactants. Modeling its adsorption at air/water interface. J Mol Liq 308:113100
Gao XR, Wang Y, Zhao XX, Wei WL, Chang HH (2016) Equilibrium and dynamic surface tension properties of Gemini quaternary ammonium salt surfactants with ester groups. Colloids Surf A 509:130–139
Ju H, Jiang Y, Geng T, Wang Y, Zhang C (2017) Equilibrium and dynamic surface tension of quaternary ammonium salts with different hydrocarbon chain length of counterions. J Mol Liq 225:606–612
Yang W, Cao Y, Wang Y, Ju H, Jiang Y, Geng T (2020) Effects of unsaturated double bonds on adsorption and aggregation behaviors of amide-based cationic Gemini surfactants. Colloids Surf A 611:125778
Chu YP, Gong Y, Tan XL, Zhang L, Zhao S, An JY, Yu JY (2004) Studies of synergism for lowering dynamic interfacial tension in sodium alpha-(n-alkyl) naphthalene sulfonate/alkali/acidic oil systems. J Colloid Interface Sci 276:182–187
Bera A, Mandal A, Guha BB (2014) Synergistic effect of surfactant and salt mixture on interfacial tension reduction between crude oil and water in enhanced oil recovery. J Chem Eng Data 59:89–96
He W, Zhang Y, Li J, Gao Y, Luo F, Tan H, Wang K, Fu Q (2016) A novel surface structure consisting of contact-active antibacterial upper-layer and antifouling sub-layer derived from Gemini quaternary ammonium salt polyurethanes. Sci Rep 6:32140
Zhi LF, Shi XF, Zhang EZ, Pan YL, Li XM, Wang H, Liu W (2021) Synthesis and properties of stellate lactosamide quaternary ammonium surfactants. Colloids Surf A 628:127317
Zhou X, Hu S, Wang Y, Ullah S, Hu J, Liu H, Xu B (2019) The surface adsorption, aggregate structure and antibacterial activity of Gemini quaternary ammonium surfactants with carboxylic counterions. Royal Soc Open Sci 6:190378
Mechken KA, Menouar M, Belkhodja M, Saidi-Besbes S (2021) Synthesis, surface properties and bioactivity of novel 4-substituted 1,2,3-triazole quaternary ammonium surfactants. J Mol Liq 338:116775
Kawai R, Yada S, Yoshimura T (2021) Adsorption and aggregation behavior of mixtures of quaternary-ammonium-salt-type amphiphilic compounds with fluorinated counterions and surfactants. Langmuir 37:11330–11337
Gul S, Saleem M, Munawar MA, Ahmad HA, Ahmed E, Begum R, Farooqi ZH (2020) Synthesis of novel quaternary ammonium salts from 1, 2-benzothiazine derivatives. J Sulfur Chem 42:15–28
Asadov ZH, Ahmadova GA, Rahimov RA, Abilova AZ, Zargarova SH, Zubkov FI (2018) Synthesis and properties of quaternary ammonium surfactants based on alkylamine, propylene oxide, and 2-chloroethanol. J Surfactants Deterg 21:247–254
Funding
Shanxi Province Patent Transformation Special Plan Project (202201027) and Sinolight Corporation Science and Technology Innovation Fund Project (ZQ2022YY05).
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
The authors declare no competing interests.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.
About this article
Cite this article
Ding, H., Jiang, Y., Wang, Y. et al. Adsorption and aggregation behavior of Gemini surfactants with organic counterions. Colloid Polym Sci 301, 1171–1184 (2023). https://doi.org/10.1007/s00396-023-05122-0
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00396-023-05122-0