Polymer Bulletin

, Volume 67, Issue 5, pp 805–814 | Cite as

Novel polystyrene bearing highly branched hexafluoropropene trimer pendants

Original Article
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Abstract

A novel styrenic monomer having hexafluoropropene trimer on the benzene ring was prepared. The highly fluorinated monomer was polymerized to yield a white powdery polymer, which was soluble in fluorinated solvents and had resistance to usual organic solvents, good water repellency, and low refractivity. In contrast to common fluoropolymers having linear-fluorinated side-chains, the polymer has a characteristic high glass transition temperature. Thus, the fluorinated polymer and copolymer with styrene are suitable for applications at elevated temperature. The polymers can replace the conventional fluorinated polyacrylates, which are used in large quantity as repellents with potentially generating perfluorooctanoic acid in the environment.

Keywords

Fluoropolymers Polystyrene Glass transition PFOA Fluorinated polymers 
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References

  1. 1.
    Guo J, Resnick P, Efimenko K, Genzer J, Desimone JM (2008) Alternative fluoropolymers to avoid the challenges associated with perfluorooctanoic acid. Ind Eng Chem Res 47:502–508CrossRefGoogle Scholar
  2. 2.
    Huang J, Meng W, Qing F (2007) Synthesis and repellent properties of vinylidene fluoride-containing polyacrylates. J Fluor Chem 128:1469–1477CrossRefGoogle Scholar
  3. 3.
    Ahlbrecht AH, Reid TS, Husted DR (1953) Fluorinated acrylates and polymers. US Patent 2,642,416Google Scholar
  4. 4.
    Bovey FA, Abere JF, Rathmann GB, Sandberg CL (1955) Fluorine-containing polymers. III. Polymers and copolymers of 1,1-dihydroperfluoroalkyl acrylates. J Polym Sci 15:520–536CrossRefGoogle Scholar
  5. 5.
    Fram P (1964) Acrylic elastomers. In: Mark HF, Gaylord NG, Bikales NM (eds) Encyclopedia of polymer science and technology, vol 1. Interscience, New York, pp 226–246Google Scholar
  6. 6.
    Hayakawa Y, Ono T (2006) Facile synthesis of polystyrene bearing highly branched perfluorinated groups. Eur Polym J 42:1357–1361CrossRefGoogle Scholar
  7. 7.
    Dmowski W, Flowers WT, Haszeldine RN (1977) The use of crown ethers in the synthesis of hexafluoropropene and tetrafluoroethylene oligomers. J Fluor Chem 9:94–96CrossRefGoogle Scholar
  8. 8.
    Nishida M, Fukaya H, Ono T (2003) Synthesis and conformational studies of methylated, highly branched fluoroolefins: gear-meshed conformational isomers. Eur J Org Chem 2003:3648–3658CrossRefGoogle Scholar
  9. 9.
    Fox HW, Zisman WA (1950) The spreading of liquids on low energy surfaces. I. Polytetrafluoroethylene. J Colloid Sci 5:514–531CrossRefGoogle Scholar
  10. 10.
    Zisman WA (1965) Improving the performance of reinforced plastics. Ind Eng Chem 57:26–34CrossRefGoogle Scholar
  11. 11.
    Tüdős F, Kelen T, Földes-Berezsnich T, Turcsányi B (1976) Analysis of linear methods for determining copolymerization reactivity ratios. III. Linear graphic method for evaluating data obtained at high conversion levels. J Macromol Sci Chem A10:1513–1540CrossRefGoogle Scholar
  12. 12.
    Ishihara K, Kogure R, Matsui K (1988) Polymerization ability of perfluoroalkyloxy group substituted styrene derivatives and their surface characteristics. Kobunshi Ronbunshu 45:653–659 (in Japanese)Google Scholar
  13. 13.
    Höpken J, Möller M (1922) Low surface energy polystyrene. Macromolecules 25:1461–1467CrossRefGoogle Scholar
  14. 14.
    Bouteiller V, Garnault AM, Teyssié D, Boileau S, Möller M (1999) Synthesis, thermal and surface characterization of fluorinated polystyrenes. Polym Int 48:765–772CrossRefGoogle Scholar
  15. 15.
    Boemer B, Sueling C, Koenig J, Hespe H, Heynemann K, Weber R (1979) Styrene polymers containing at least 3 fluorine atoms per molecule and their use. Ger Offen DE 2,936,131Google Scholar
  16. 16.
    Andrews RJ, Grulke EA (1999) Glass transition temperatures of polymers. In: Brandrup J, Immergut EH, Grulke EA (eds) Polymer handbook, 4th edn. Wiley, New York, p VI/193Google Scholar

Copyright information

© Springer-Verlag 2010

Authors and Affiliations

  1. 1.National Institute of Advanced Industrial Science and Technology (AIST)NagoyaJapan

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