Synthesis and Properties of a Novel Fluorinated Surfactant via “Thiol-ene” Click Reaction

Shuyan Liu, Yabin Zhang, Congcong Zhai, Luqing Zhang, Chuanyong Zong, Jiachen Ma, Zhiyuan Huo, Shuxiang Zhang

2018

Abstract

To meet the urgent requirment for the green fluorinated surfactants in practical applications, a novel fluorinated surfactant was synthesized in a facile two-step procedure. Firstly, (1,1,2-trifluoro-2-heptafluoropropyloxy-ethylsulfanyl)-acetic acid (THEA), i.e. F(CF2)3OCFHCF2SCH2COOH, was prepared via “thiol-ene” click reaction between heptafluoropropyl trifluorovinyl ether (PPVE) and 2-mercaptoacetic acid (TGA), and then THEA was neutralized with sodium hydroxide to obtain the targeted surfactant (1,1,2-trifluoro-2-heptafluoropropyloxy-ethylsulfanyl)-sodium acetate (THESA), i.e. F(CF2)3OCFHCF2SCH2COONa. The structure of this surfactant was characterized by 1H NMR, 19F NMR and FT-IR in detail. The surface properties of THESA were measured by the ring method, and the results demonstrated that the novel fluorinated surfactant exhibited lower surface tension (15.86 mN·m-1) and critical micelle concentration (CMC, 20 mmol·L-1), compared with the conventional fluorocarbon surfactant, ammonium perfluorooctanoate (PFOA). The results presented in this work indicated that this novel fluorinated surfactant with excellent surface properties via versatile synthetic strategy, could be a promising candidate to overcome the limitations of the traditional fluorinated surfactant, such as PFOA.

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Paper Citation


in Harvard Style

Liu S., Zhang Y., Zhai C., Zhang L., Zong C., Ma J., Huo Z. and Zhang S. (2018). Synthesis and Properties of a Novel Fluorinated Surfactant via “Thiol-ene” Click Reaction.In The Second International Conference on Materials Chemistry and Environmental Protection - MEEP, ISBN 978-989-758-360-5, pages 55-58. DOI: 10.5220/0008185400550058


in Bibtex Style

@conference{meep18,
author={Shuyan Liu and Yabin Zhang and Congcong Zhai and Luqing Zhang and Chuanyong Zong and Jiachen Ma and Zhiyuan Huo and Shuxiang Zhang},
title={Synthesis and Properties of a Novel Fluorinated Surfactant via “Thiol-ene” Click Reaction},
booktitle={The Second International Conference on Materials Chemistry and Environmental Protection - MEEP,},
year={2018},
pages={55-58},
publisher={SciTePress},
organization={INSTICC},
doi={10.5220/0008185400550058},
isbn={978-989-758-360-5},
}


in EndNote Style

TY - CONF

JO - The Second International Conference on Materials Chemistry and Environmental Protection - MEEP,
TI - Synthesis and Properties of a Novel Fluorinated Surfactant via “Thiol-ene” Click Reaction
SN - 978-989-758-360-5
AU - Liu S.
AU - Zhang Y.
AU - Zhai C.
AU - Zhang L.
AU - Zong C.
AU - Ma J.
AU - Huo Z.
AU - Zhang S.
PY - 2018
SP - 55
EP - 58
DO - 10.5220/0008185400550058