Surface activity, salt and pH tolerance, and wettability of novel nonionic fluorinated surfactants with a short fluorocarbon chain

References

• Zaggia, A. ; Ameduri, B. Recent Advances on Synthesis of Potentially Non-Bioaccumulable Fluorinated Surfactants. Curr. Opin. Colloid. In. 2012, 17 , 188–195. DOI: 10.1016/j.cocis.2012.04.001.
   Web of Science ®Google Scholar
• Zhang, L. ; Geng, B. ; Lu, Q. ; Xu, A. ; Zhang, S. Synthesis and Surface Activities of Novel Succinic Acid Double-Tailed Sulfonate Fluorinated Surfactants. J. Surfact. Deterg. 2016, 19 , 559–565. DOI: 10.1007/s11743-016-1802-2.
   Web of Science ®Google Scholar
• Shinoda, K. ; Hato, M. ; Hayashi, T. The Physicochemical Properties of Aqueous Solutions of Fluorinated Surfactants. J. Phys. Chem. 1972, 76 , 909–914. DOI: 10.1021/j100650a021.
   Web of Science ®Google Scholar
• Song, A. ; Dong, S. ; Hao, J. ; Liu, W. ; Xu, G. ; Wang, H. Functions of Fluorosurfactants 1: Surface Activities-Improved and Vesicle Formation of The Short-Tailed Chain Sulfonate Salt Mixed with a Fluorosurfactant. J. Fluorine Chem. 2005, 126 , 1266–1273. DOI: 10.1016/j.jfluchem.2005.06.005.
   Web of Science ®Google Scholar
• Fisicaro, E. ; Contardi, L. ; Compari, C. ; Bacciottini, F. ; Pongiluppi, E. ; Viscardi, G. ; Barbero, N. ; Quagliotto, P. ; Różycka-Roszak, B. Solution Thermodynamics of Highly Fluorinated Gemini Bispyridinium Surfactants for Biomedical Applications. Colloids Surf. A 2016, 507 , 236–242. DOI: 10.1016/j.colsurfa.2016.07.051.
   Google Scholar
• Peng, Y-y. ; Lu, F. ; Tong, Q.-X. One-Step Synthesis, Wettability and Foaming Properties of High-Performance Non-Ionic Hydro-Fluorocarbon Hybrid Surfactants. Appl. Surf. Sci. 2018, 433 , 264–270. DOI: 10.1016/j.apsusc.2017.10.012.
   Web of Science ®Google Scholar
• Zhao, M. ; Yu, Y. ; Han, Z. ; Li, H. Preparation of a Fluorocarbon Polymerizable Surfactant and Its Application in Emulsion Polymerization of Fluorine-Containing Acrylate. Polymers 2017, 9 , 606. DOI: 10.3390/polym9110606.
   Web of Science ®Google Scholar
• Wang, J. ; Wang, S. ; Lin, W. ; Kang, Z. ; You, Q. Formula Optimization and Rheology Study of Clean Fracturing Fluid. J. Mol. Liq. 2017, 241 , 563–569. DOI: 10.1016/j.molliq.2017.06.050.
   Web of Science ®Google Scholar
• Song, Y. ; Wu, S. ; Yang, Q. ; Liu, H. ; Zeng, Y. ; Shi, B. Factors Affecting Mass Transfer of Protease in Pelt during Enzymatic Bating Process. J. Leather Sci. Eng. 2019, 1 , 4. DOI: 10.1186/s42825-019-0007-7.
   Google Scholar
• Krafft, M. P. ; Riess, J. G. Per- and Polyfluorinated Substances (PFASs): Environmental Challenges. Curr. Opin. Colloid. In. 2015, 20 , 192–212. DOI: 10.1016/j.cocis.2015.07.004.
   Web of Science ®Google Scholar
• Kann, K. ; Corsolini, S. ; Falandysz, J. ; Oehme, G. ; Focardi, S. ; Giesy, J. Perfluorooctanesulfonate and Related Fluorinated Hydrocarbons in Marine Mammals, Fishes, and Birds from Coasts of the Baltic and the Mediterranean Seas. Environ. Sci. Technol. 2002, 36 , 3210–3216. DOI: 10.1021/es020519q.
   PubMed Web of Science ®Google Scholar
• Wang, T. ; Wang, Y. ; Liao, C. ; Cai, Y. Q. ; Jiang, G. B. Perspectives on the Inclusion of Perfluorooctane Sulfonate into the Stockholm Convention on Persistent Organic Pollutants. Environ. Sci. Technol. 2009, 43 , 5171–5175. DOI: 10.1021/es900464a.
   PubMed Web of Science ®Google Scholar
• Sha, M. ; Xing, P. ; Jiang, B. Strategies for Synthesizing Non-Bioaccumulable Alternatives to PFOA and PFOS. Chinese Chem. Lett. 2015, 26 , 491–498. DOI: 10.1016/j.cclet.2015.03.038.
   Web of Science ®Google Scholar
• Pearlson, W. H. The Simons Electrochemical Fluorination Process (Commercial Development at 3M). J. Fluorine Chem. 1986, 32 , 29–40. DOI: 10.1016/S00221139(00)80505-9.
   Web of Science ®Google Scholar
• Yang, M. ; Hao, J. ; Li, H. Syntheses and Aggregation Behavior of Pyridine-Based CH–CF Hybrid Surfactants. J. Fluorine Chem. 2014, 165 , 81–90. DOI: 10.1016/j.jfluchem.2014.06.001.
   Web of Science ®Google Scholar
• Paria, S. ; Khilar, K. C . A Review on Experimental Studies of Surfactant Adsorption at the Hydrophilic Solid-Water Interface. Adv. Colloid Interface Sci. 2004, 110 , 75–95. DOI: 10.1016/j.cis.2004.03.001.
   PubMed Web of Science ®Google Scholar
• Kiani, M. ; SaadatAbadi, A. R. ; Behbahani, T. J. Wettability Alteration of Carbonate Rock by Nonionic Surfactants in Water-Based Drilling Fluid. Int. J. Environ. Sci. Technol. 2019, 16 , 6547–6556. DOI: 10.1007/s13762-018-1932-3.
   Web of Science ®Google Scholar
• Boussambe, G. N. M. ; Guillet, P. ; Mahler, F. ; Marconnet, A. ; Vargas, C. ; Cornut, D. ; Soulié, M. ; Ebel, C. ; Le Roy, A. ; Jawhari, A. ; et al. Fluorinated Diglucose Detergents for Membrane-Protein Extraction. Methods 2018, 147 , 84–94. DOI: 10.1016/j.ymeth.2018.05.025.
   PubMed Web of Science ®Google Scholar
• Bongartz, N. ; Patil, S. R. ; Stubenrauch, C. ; Blunk, D. A New Fluorinated Inositol-Based Surfactant. Colloids Surf. A 2012, 414 , 320–326. DOI: 10.1016/j.colsurfa.2012.08.053.
   Google Scholar
• Fei, L. ; Ge, F. ; Yin, Y. ; Wang, C. Photo-Responsive Foam Control Base on Nonionic Azobenzene Surfactant as Stabilizer. Colloids Surf. A 2019, 560 , 366–375. DOI: 10.1016/j.colsurfa.2018.10.038.
   Google Scholar
• Calvo, E. ; Bravo, R. ; Amigo, A. ; Gracia, F. J. Dynamic Surface Tension, Critical Micelle Concentration, and Activity Coefficients of Aqueous Solutions of Nonyl Phenol Ethoxylates. Fluid Phase Equilibria 2009, 282 , 14–19. DOI: 10.1016/j.fluid.2009.04.016.
   Web of Science ®Google Scholar
• Sis, H. ; Chander, G. ; Chander, S. Synergism in Sodium Oleate/Ethoxylated Nonylphenol Mixtures. J. Disper. Sci. Technol. 2005, 26 , 605–614. DOI: 10.1081/DIS-200057666.
   Web of Science ®Google Scholar
• Yin, Q. ; Xue, W. ; Bai, Y. ; Wang, W. ; Ma, X. ; Du, Z. ; Wang, G. Micellization and Aggregation Properties of Sodium Perfluoropolyether Carboxylate in Aqueous Solution. J. Ind. Eng. Chem. 2016, 42 , 63–68. DOI: 10.1016/j.jiec.2016.07.026.
   Web of Science ®Google Scholar
• Sagisaka, M. ; Iwama, S. ; Hasegawa, S. ; Yoshizawa, A. ; Mohamed, A. ; Cummings, A. ; Rogers, S. E. ; Heenan, R. K. ; Eastoe, J. Super-Efficient Surfactant for Stabilizing Water-in-Carbon Dioxide Microemulsions. Langmuir 2011, 27 , 5772–5780. DOI: 10.1021/la104990c.
   PubMed Web of Science ®Google Scholar
• Liu, B. ; Tang, X. ; Fang, W. ; Li, X. ; Zhang, J. ; Zhang, Z. ; Shen, Y. ; Yan, Y. ; Sun, X. ; He, J. Molecular Dynamics Study of di-CF4 Based Reverse Micelles in Supercritical CO2 . Phys. Chem. Chem. Phys. 2016, 18 , 29156–29163. DOI: 10.1039/c6cp04253h.
   PubMedGoogle Scholar
• Kang, E-k. ; Sohn, E.-H. ; Jung, G. Y. ; Jung, S. H. ; Ha, J.-W. ; Lee, S.-B. ; Park, I. J. ; Lee, B. M. Synthesis, Interfacial Property, and Application of New Hybrid Anion Surfactant Containing Fluorocarbon and Hydrocarbon Chains. J. Ind. Eng. Chem. 2018, 67 , 72–79. DOI: 10.1016/j.jiec.2018.06.016.
   Web of Science ®Google Scholar
• Wang, Z. ; Li, P. ; Ma, K. ; Chen, Y. ; Campana, M. ; Penfold, J. ; Thomas, P. K. ; Roberts, D. W. ; Xu, H. ; Petkov, J. T. ; Yan, Z. Impact of Molecular Structure, Headgroup and Alkyl Chain Geometry, on the Adsorption of the Anionic Ester Sulfonate Surfactants at The Air-Solution Interface, in the Presence and Absence of Electrolyte. J. Colloid Interface Sci. 2019, 544 , 293–302. DOI: 10.1016/j.jcis.2019.03.011.
   PubMed Web of Science ®Google Scholar
• Crook, E. H. ; Fordyce, D. B. ; Trebbi, G. F. Molecular Weight Distribution of Nonionic Surfactants. I. Surface and Interfacial Tension of Normal Distribution and Homogeneous p, t-Octylphenoxyethoxyethanols (OPE’S). J. Phys. Chem. 1963, 67 , 1987–1994. DOI: 10.1021/j100804a010.
   Web of Science ®Google Scholar
• Li, C. ; Yu, H. ; Li, F. ; Zhang, Z. ; Huang, J. ; Wang, J. Physicochemical Properties of Series of Cardanol Polyoxyethylene Ether Carboxylates with Different Ethoxylation Unit at the Interface. J. Disper. Sci. Technol. 2019, 40 , 9–16. DOI: 10.1080/01932691.2018.1462711.
   Web of Science ®Google Scholar
• Lyu, Y. ; Brusseau, M. L. ; Chen, W. ; Yan, N. ; Fu, X. ; Lin, X. Adsorption of PFOA at the Air-Water Interface during Transport in Unsaturated Porous Media. Environ. Sci. Technol. 2018, 52 , 7745–7753. DOI: 10.1021/acs.est.8b02348.
   PubMed Web of Science ®Google Scholar
• Czajka, A. ; Hazell, G. ; Eastoe, J. Surfactants at the Design Limit. Langmuir 2015, 31 , 8205–8217. DOI: 10.1021/acs.langmuir.5b00336.
   PubMed Web of Science ®Google Scholar
• Tang, J. ; Liu, Y. ; Wang, C. ; Niu, X. ; Tan, B. ; Gao, B. Application of Surfactant for Facilitating Benzotriazole Removal and Inhibiting Copper Corrosion during Post-CMP Cleaning. Microelectron. Eng. 2018, 202 , 1–8. DOI: 10.1016/j.mee.2018.09.005.
   Web of Science ®Google Scholar
• Armstrong, J. K. ; Leharne, S. A. ; Stuart, B. H. ; Martin, J. S. ; Chowdhry, B. Z. Phase Transition Properties of Poly(Ethylene Oxide) in Aqueous Solutions of Sodium Chloride. Langmuir 2001, 17 , 4482–4485. DOI: 10.1021/la010339e.
   Web of Science ®Google Scholar
• Zhang, L. ; Zhang, X. ; Zhang, P. ; Zhang, Z. ; Liu, S. ; Han, B. Efficient Emulsifying Properties of Glycerol-Based Surfactant. Colloids Surf. A 2018, 553 , 225–229. DOI: 10.1016/j.colsurfa.2018.05.055.
   Google Scholar
• Brusseau, M. L. ; Glubt, V. S. The Influence of Surfactant and Solution Composition on PFAS Adsorption at Fluid-Fluid Interfaces. Water Res. 2019, 161 , 17–26. DOI: 10.1016/j.watres.2019.05.095.
   PubMed Web of Science ®Google Scholar
• Wang, H. ; Wei, X. ; Du, Y. ; Wang, D. Effect of Water-Soluble Polymers on the Performance of Dust-Suppression Foams: Wettability, Surface Viscosity and Stability. Colloids Surf. A 2019, 568 , 92–98. DOI: 10.1016/j.colsurfa.2019.01.062.
   Google Scholar
• Rosen, M. J. The Relationship of Structure to Properties in Surfactants. J. Am. Oil Chem. Soc. 1972, 49 , 293–297. DOI: 10.1007/BF02637577.
   Web of Science ®Google Scholar
• Thakkar, K. ; Bharatiya, B. ; Ray, D. ; Aswal, V. K. ; Bahadur, P. Molecular Interactions Involving Aqueous Triton X-100 Micelles and Anionic Surfactants: Investigations on Surface Activity and Morphological Transitions. J. Mol. Liq. 2016, 223 , 611–620. DOI: 10.1016/j.molliq.2016.08.086.
   Web of Science ®Google Scholar
• Chen, C.-P. ; Lu, F. ; Tong, Q.-X. Three Tetrasiloxane-Tailed Cationic Gemini Surfactants: The Effect of Different Spacer Rigidity on Surface Properties and Aggregation Behaviors. J. Mol. Liq. 2018, 266 , 504–513. DOI: 10.1016/j.molliq.2018.06.112.
   Web of Science ®Google Scholar