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Synthesis and Surface Activities of Novel Succinic Acid Monofluoroalkyl Sulfonate Surfactants

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Journal of Surfactants and Detergents

Abstract

Two environmentally friendly succinic acid monofluoroalkyl sulfonate surfactants were synthesized from maleic anhydride and polyethylene glycol mono (1H,1H,7H-dodecafluoroheptyl) ether, i.e. H(CF2)6CH2OCH2CH2OCOCH(SO3Na)CH2COOH (FEOS-1) and H(CF2)6CH2(OCH2CH2)3OCOCH(SO3Na)CH2COOH (FEOS-3). The obtained surfactants were characterized by FT-IR, 1H NMR, 13C NMR and 19F NMR in detail. The synthesized fluorinated surfactants have a high thermal stability on the basis of thermogravimetric analysis. Their surface properties were examined and the results show that FEOS-1 and FEOS-3 surfactants can reduce the surface tension of water to 25.55 mN m−1 at 10.25 mmol L−1 and 21.63 mN m−1 at 8.33 mmol L−1, respectively; meanwhile, the introduction of oxyethylene groups enhances the hydrophilicity and micellar forming ability and the longer oxyethylene chains the better surface properties. The Krafft points (K p) of FEOS-1 and FEOS-3 were both below 0 °C, which was lower than perfluoro-n-heptanesulfonic acid sodium salt (n-C7F15SO3Na, K p = 56.5 °C) at a similar length of fluorocarbon chains. Comparison studies on two surfactants above and the conventional fluorocarbon surfactants, perfluorooctanoate of ammonium (PFOA) show that the surfactants have comparable properties to PFOA, thus offering an environmentally friendly synthesizing alternatives to PFOA.

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Acknowledgments

This project was financially supported by the National Natural Science Foundation of China (No. 20774037).

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Authors and Affiliations

  1. Shandong Provincial Key Laboratory of Fluorine Chemistry and Chemical Materials, Jinan, 250022, China

    Luqing Zhang, Jinhui Shi, Anhou Xu, Bing Geng & Shuxiang Zhang

  2. School of Chemistry and Chemical Engineering, University of Jinan, Jinan, 250022, China

    Luqing Zhang, Jinhui Shi, Anhou Xu, Bing Geng & Shuxiang Zhang

  3. Shandong Engineering Research Center for Fluorinated Material, Jinan, 250022, China

    Luqing Zhang, Jinhui Shi, Anhou Xu, Bing Geng & Shuxiang Zhang

Authors
  1. Luqing Zhang
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  2. Jinhui Shi
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  3. Anhou Xu
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  4. Bing Geng
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  5. Shuxiang Zhang
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Correspondence to Shuxiang Zhang.

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Zhang, L., Shi, J., Xu, A. et al. Synthesis and Surface Activities of Novel Succinic Acid Monofluoroalkyl Sulfonate Surfactants. J Surfact Deterg 16, 183–190 (2013). https://doi.org/10.1007/s11743-012-1366-8

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  • DOI: https://doi.org/10.1007/s11743-012-1366-8

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