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Synthesis and Characterization of a Novel Class of Zwitterionic Fluorocarbon Surfactants Based on Perfluorobutyl

Synthese und Charakterisierung einer neuen Klasse von zwitterionischen Fluorkohlenstoff-Tensiden auf Basis von Perfluorbutyl.
  • Xuhong Jia

    Xuhong Jia, Academic staff (associate professor) at College of Civil Aviation Safety Engineering, Civil Aviation Flight University of China, Guanghan, China. Research area is organic synthesis in novel surfactants development.

         , Rui Huang

    Rui Huang, Graduate student of College of Civil Aviation Safety Engineering, Civil Aviation Flight University of China.

         , Xiaoguang Yang

    Xiaoguang Yang, Graduate student of College of Civil Aviation Safety Engineering, Civil Aviation Flight University of China.

         , Wan Tao

    Wan Tao, Graduate student of College of Civil Aviation Safety Engineering, Civil Aviation Flight University of China.

         and Xinhua Zhu

    Xinhua Zhu, Academic staff (lecturer) at College of Civil Aviation Safety Engineering, Civil Aviation Flight University of China, Guanghan, China. Research area is organic synthesis in novel surfactants development.

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Published/Copyright: March 13, 2021
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Tenside Surfactants Detergents
From the journal Tenside Surfactants Detergents Volume 58 Issue 2

Abstract

Perfluorooctane sulfonate (PFOS) and its derivatives had been banned due to their potential environmental hazards, although they possessed excellent surface activity. An effective method to solve this problem was to shorten the fluorocarbon chain of these surfactants from C°H17 to C4F9. As previous studies had shown, zwitterionic surfactants possess higher surface activity but have lower toxicity compared to other types of surfactants. In view of this, a class of novel zwitterionic fluorocarbon surfactants (n-CFNA-Br) with perfluorobutyl moiety was synthesized in this work. Their structures were characterized by FTIR, 1H NMR, 13C NMR, 19F NMR and MS. The results showed that all synthesized n-CFNA-Br had almost the same minimum surface tension, but their critical micelle concentration (CMC) decreased with increasing length of hydrophobic carbon chain. In pure water, the surface tension at the CMC (γCMC) of the four n-CFNA-Br were about 20 mN/m, and the CMC values were 7.73 mmol/L for 1-CFNA-Br, 4.70 mmol/L for 2-CFNA-Br, 4.13 mmol/L for 3-CFNA-Br, and 3.36 mmol/L for 4-CFNA-Br, indicating high efficiency and effectiveness. In 0.1 mol/L NaCl, the CMC values reduced to less than half of the CMC values measured in the pure aqueous surfactant solution, while the surface tensions γCMC remained almost unchanged, indicating good salinity tolerance of the synthesized surfactants. The acidic surfactant solutions exhibited similar CMC values to the saline solutions, but the surface tension γCMC increased slightly to 25 mN/m. However, further investigation showed that the n-CFNA-Br surfactants exhibited poor surface activity in alkaline solution (0.1 mol/L NaOH). In the pH range of 6.6 to 10.4, white precipitates appeared in the surfactant solutions after some time, indicating that the n-CFNA-Br are not suitable for use in alkaline systems with pH greater than 6.6.

Abstract

Perfluoroctansulfonat (PFOS) und seine Derivate waren aufgrund ihrer potentiellen Umweltschädlichkeit verboten worden, obwohl sie eine ausgezeichnete Oberflächenaktivität besaßen. Eine effektive Methode zur Lösung dieses Problems war die Verkürzung der Fluorkohlenstoffkette dieser Tenside von C°H17 auf C4F9. Wie frühere Studien gezeigt hatten, besitzen zwitterionische Tenside eine höhere Oberflächenaktivität, haben aber eine geringere Toxizität im Vergleich zu anderen Arten von Tensiden. In Anbetracht dessen wurde in dieser Arbeit eine Klasse neuartiger zwitterionischer Fluorkohlenstoff-Tenside (n-CFNA-Br) mit Perfluorbutyl-Teil synthetisiert. Ihre Strukturen wurden mittels FTIR, 1H NMR, 13C NMR, 19F NMR und MS charakterisiert. Die Ergebnisse zeigten, dass alle synthetisierten n-CFNA-Br fast die gleiche minimale Oberflächenspannung (γCMC) haben, ihre kritische Mizellenkonzentration (CMC) nahm aber mit zunehmender Länge der hydrophoben Kohlenstoffkette ab. Im reinen Wasser lagen die γCMC der vier n-CFNA-Br bei etwa 20 mN/m und die CMC-Werte betrugen 7,73 mmol/L für 1-CFNA-Br, 4,70 mmol/L für 2-CFNA-Br, 4,13 mmol/L für 3-CFNA-Br und 3,36 mmol/L für 4-CFNA-Br, was auf eine hohe Effizienz und Effektivität der Tenside hinweist. In der NaCl-Lösung (0.1 mol/L) reduzierten sich die CMC-Werte auf weniger als die Hälfte der CMC-Werte, die in reiner wässriger Tensidlösung gemessen wurden, während die Oberflächenspannung γCMC fast unverändert blieb, was auf eine gute Salzgehaltstoleranz der synthetisierten Tenside hindeutete. Die sauren Tensidlösungen wiesen ähnliche CMC-Werte wie die salzhaltigen Lösungen auf, aber die Oberflächenspannung γCMC stieg leicht auf 25 mN/m an. Die weiteren Untersuchungen zeigten jedoch, dass die n-CFNA-Br-Tenside in alkalischer Lösung (0,1 mol/L NaOH) eine schlechte Oberflächenaktivität aufwiesen. Im pH-Bereich von 6,6 bis 10,4 traten nach einiger Zeit weiße Ausfällungen in den Tensidlösungen auf, was darauf hindeutet, dass die n-CFNA-Br nicht für die Verwendung in alkalischen Systemen mit einem pH-Wert größer als 6,6 geeignet sind.

Key words: Zwitterionic; surfactants; perfluorobutyl; synthesis; characterization; surface activity
Stichwörter: Zwitterionische Tenside; Perfluorobutyl; Synthese; Charakterisierung; Oberflächenaktivität
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About the authors

Xuhong Jia

Xuhong Jia, Academic staff (associate professor) at College of Civil Aviation Safety Engineering, Civil Aviation Flight University of China, Guanghan, China. Research area is organic synthesis in novel surfactants development.

Rui Huang

Rui Huang, Graduate student of College of Civil Aviation Safety Engineering, Civil Aviation Flight University of China.

Xiaoguang Yang

Xiaoguang Yang, Graduate student of College of Civil Aviation Safety Engineering, Civil Aviation Flight University of China.

Wan Tao

Wan Tao, Graduate student of College of Civil Aviation Safety Engineering, Civil Aviation Flight University of China.

Dr. Xinhua Zhu

Xinhua Zhu, Academic staff (lecturer) at College of Civil Aviation Safety Engineering, Civil Aviation Flight University of China, Guanghan, China. Research area is organic synthesis in novel surfactants development.

Acknowledgements

This work was supported by National Key R&D Program of China (No. 2018YFC0809500) and Security Capacity Building Project of the Civil Aviation Administration of China (No. 0241930).

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Received: 2020-08-13
Accepted: 2020-12-27
Published Online: 2021-03-13

© 2021 Walter de Gruyter GmbH, Berlin/Boston

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https://doi.org/10.1515/tsd-2020-2302
Keywords for this article
Zwitterionic; surfactants; perfluorobutyl; synthesis; characterization; surface activity

Articles in the same Issue

  1. Contents
  2. Environmental Chemistry
  3. Biodegradability of Polyvinyl Alcohol Based Film Used for Liquid Detergent Capsules
  4. Application
  5. Effects of Laundering on Moisture Management and Air Permeability of Different Chitosan Treated Nylon 6,6 Elastane Fabrics Using EDTA and Triton X-100
  6. Application of Newly Synthesized Sulfobetaine Based on Sweet Almond Oil in Bath Liquids for Sensitive Skin
  7. Preparation of Silicone Emulsion Defoamer with Easy Separation of Magnetic Hydrophobic Nanoparticles
  8. Bentonite Suspension Filtration and its Electro-Kinetics in the Presence of Additives
  9. Novel surfactants
  10. Synthesis and Properties of Alkyl Bis-Guanidinium Acetates Surfactants
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  12. Physical Chemistry
  13. Interfacial Behaviour of Saponin Based Surfactant for Potential Application in Cleaning
  14. Synthesis
  15. Preparation and the Foaming Activity Study of Hydroxymethyl Cetyltrimethyl Ammonium Chloride
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