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CF3CF2CF2C(CF3)2-based fluorinated surfactants with high surface activity

  • Ding Zhang
  • Min Sha
  • Renming Pan
  • Xiangyang LinEmail author
  • Ping XingEmail author
  • Biao JiangEmail author
Original Paper
  • 23 Downloads

Abstract

The ever-increasing environmental and toxicity concerns have resulted in the widespread development of fluorosurfactants without long perfluorinated chain (≥ C8). The surveys have reported that perfluoroether chains are easier to degrade than fluorinated chains due to the better flexibility of ether bond. Herein, four novel kinds of fluorosurfactants with a perfluorinated branched ether chain were reported, which can be synthesized via a simple and economical route. These surfactants all exhibited extremely high surface activity. The effect of salt and pH on the surface activities of the newly prepared surfactants were studied. The results showed that these surfactants possessed excellent acid and alkali resistance except that the anionic surfactant was slightly sensitive to acid. Interfacial tension of oil/water and thermodynamic properties of the surfactants were further investigated for the purpose of special applications. This series of surfactants had great thermal stability and the fluorinated cationic surfactant can spread on the oil surface under the condition of low concentration. These excellent properties indicate that these surfactants possess good prospect for industrial applications.

Keywords

Fluorinated surfactant Perfluoroether chain Surface activity Salt effect pH influence Thermodynamic property 

Notes

Acknowledgements

This project was financially supported by the National Natural Science Foundation of China (NSFC2167020782).

Supplementary material

11696_2019_701_MOESM1_ESM.doc (1.1 mb)
Supplementary material 1 (DOC 1166 kb) 1H NMR, 19F NMR, 13C NMR for the novel compounds fluorinated surfactants and all the intermediates are provided

References

  1. Abe M (1999) Synthesis and applications of surfactants containing fluorine. Curr Opin Colloid in 4:354–356CrossRefGoogle Scholar
  2. Dichiarante V, Milani R, Metrangolo P (2018) Natural surfactants towards a more sustainable fluorine chemistry. Green Chem 20:13–27.  https://doi.org/10.1039/c7gc03081a CrossRefGoogle Scholar
  3. Fanga C, Megharaj M, Naidu R (2016) Electrochemical detection of thioether-based fluorosurfactants in aqueous film-forming foam (AFFF). Electroanalysis 29:1095–1102.  https://doi.org/10.1002/elan.201600724 CrossRefGoogle Scholar
  4. Gardiner J (2015) Fluoropolymers: origin, production, and industrial and commercial applications. Aust J Chem 68:13–22.  https://doi.org/10.1071/CH14165 CrossRefGoogle Scholar
  5. Griffiths PC, Cheung AYF, Jenkins RL, Howe AM, Pitt AR, Heenan RK, King SM (2004) Interaction between a partially fluorinated alkyl sulfate and gelatin in aqueous solution. Langmuir 20:1161–1167.  https://doi.org/10.1021/la035956c CrossRefGoogle Scholar
  6. Harkins WD, Feldman A (1922) Films. The spreading of liquids and the spreading coefficient. J Am Chem Soc 44:2665–2685CrossRefGoogle Scholar
  7. Huo T, Huang Y, Meng WD (2014) Preparation of perfluoropolyether-containing poly-methacrylate emulsion and their application on cotton fabrics. J Donghua Univ 40:90–98.  https://doi.org/10.3969/j.issn.1671-0444.2014.01.016 Google Scholar
  8. Kissa E (2001) Fluorinated surfactants and repellents. Marcel Dekker Inc, New YorkGoogle Scholar
  9. Kostov G, Boschet F, Ameduri B (2009) Original fluorinated surfactants potentially non-bioaccumulable. J Fluorine Chem 130:1192–1199.  https://doi.org/10.1016/j.jfluchem.2009.08.002 CrossRefGoogle Scholar
  10. Lin C, Pan RM, Xin P, Jiang B (2018a) Synthesis and combined properties of novel fluorinated cationic surfactants with CF3CF2CF2C(CF3)2- group. Chin Chem Lett.  https://doi.org/10.1016/j.cclet.2018.04.017 in press Google Scholar
  11. Lin C, Pan RM, Xin P, Jiang B (2018b) Synthesis and surface activity study of novel branched zwitterionic heterogemini fluorosurfactants with CF3CF2CF2C(CF3)2 group. J Fluorine Chem 214:35–41.  https://doi.org/10.1016/j.jfluchem.2018.07.015 CrossRefGoogle Scholar
  12. Malinverno G, Colombo I, Visca M (2005) Toxicological profile of hydrofluoropolyethers. Regul Toxicol Pharm 41:228–239CrossRefGoogle Scholar
  13. Munoz G, Desrosiers M, Duy SV, Labadie P, Budzinski H, Liu J, Sauvé S (2017) Environmental occurrence of perfluoroalkyl acids and novel fluorotelomer surfactants in the freshwater fish catostomus commersonii and sediments following firefighting foam deployment at the Lac-Mégantic railway accident. Enviro Sci Technol 51:1231–1240.  https://doi.org/10.1021/acs.est.6b05432 CrossRefGoogle Scholar
  14. Pierozan P, Karlsson O (2018) PFOS induces proliferation, cell-cycle progression, and malignant phenotype in human breast epithelial cells. Arch Toxicol 92:705–716.  https://doi.org/10.1007/s00204-017-2077-8 CrossRefGoogle Scholar
  15. Rosen MJ, Kunjappu JT (2012) Surfactants and interfacial phenomena, 4th edn. JohnWiley & Son, NewYorkCrossRefGoogle Scholar
  16. Scherer KV Jr, Terranova TF (1981) F-2-methyl-2-pentanol. An easily prepared perfluorinated tertiary alcohol. J Org Chem 46:2379–2381CrossRefGoogle Scholar
  17. Sha M, Pan RM, Jiang B (2013) One-Pot catalytic epoxidation reaction of perfluoro-2-methyl-2-pentene with tri-n-butylamine N-oxide or N, N-dimethylcyclohexylamine N-oxide. Adv Mater Res 685:357–361.  https://doi.org/10.4028/www.scientific.net/AMR.685.357 CrossRefGoogle Scholar
  18. Sha M, Pan R, Zhan L, Xing P, Jiang B (2014) Synthesis and surface activity study of a novel branched fluorinated anion surfactant with CF3CF2CF2C(CF3)2 group. Chin J Org Chem 32:995–998.  https://doi.org/10.1002/cjoc.201400377 CrossRefGoogle Scholar
  19. Sha M, Pan R, Xing P, Jiang B (2015a) Synthesis and surface activity study of branched fluorinated cationic (FCS), gemini (FGS) and amphoteric (FAS) surfactants with CF3CF2CF2C(CF3)2 group. J Fluorine Chem 169:61–65.  https://doi.org/10.1016/j.jfluchem.2014.11.005 CrossRefGoogle Scholar
  20. Sha M, Xing P, Jiang B (2015b) Strategies for synthesizing non-bioaccumulable alternatives to PFOA and PFOS. Chin Chem Lett 26:491–498.  https://doi.org/10.1016/j.cclet.2015.03.038 CrossRefGoogle Scholar
  21. Sha M, Zhang D, Pan RM, Xin P, Jiang B (2015c) Synthesis and properties study of novel branched fluorinated surfactants with CF3CF2CF2C(CF3)2 group. Acta Chim Sinica 73:395–402.  https://doi.org/10.6023/a15030174 CrossRefGoogle Scholar
  22. Shi HX, Zhao LJ, Xiang JP, Gao LD, Shen HM (2009) Application of fluorinated surfactants in oil field. Fine Chem 26:331–335 (in Chinese) Google Scholar
  23. Yang BQ, Xing H, Xiao JX (2009) Perfluorobutyl-based fluorinated surfactant with high surface activity. Acta Phys Chim Sin 25:2409–2412.  https://doi.org/10.3866/PKU.WHXB20091204 Google Scholar
  24. Zhang Q, Luo Z, Curran DP (2000) Separation of “Light Fluorous” reagents and catalysts by fluorous solid-phase extraction: synthesis and study of a family of triarylphosphines bearing linear and branched fluorous tags. J Org Chem 65:8866–8873.  https://doi.org/10.1021/jo000464f CrossRefGoogle Scholar
  25. Zhang D, Sha M, Pan RM, Lin XY, Xing P, Jiang B (2018a) Design and synthesis of the novel branched fluorinated surfactant intermediates with CF3CF2CF2C(CF3)2 group. Chin Chem Lett.  https://doi.org/10.1016/j.cclet.2018.11.014 (in press) Google Scholar
  26. Zhang D, Sha M, Pan RM, Lin XY, Xing P, Jiang B (2018b) Synthesis and properties study of novel fluorinated surfactants with perfluorinated branched ether chain. J Fluorine Chem.  https://doi.org/10.1016/j.jfluchem.2018.11.001 (in press) Google Scholar

Copyright information

© Institute of Chemistry, Slovak Academy of Sciences 2019

Authors and Affiliations

  1. 1.School of Chemical EngineeringNanjing University of Science and TechnologyNanjingPeople’s Republic of China
  2. 2.CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic ChemistryChinese Academy of SciencesShanghaiPeople’s Republic of China
  3. 3.School of Management Science & EngineeringNanjing University of Finance & EconomicsNanjingPeople’s Republic of China

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