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    Synthesis of fluorinated polypropylene using CuAAC click chemistry

    Year: 2019

    Journal: J. Appl. Polym. Sci., Volume 136, FEB 15

    Authors: Acik, G.; Cansoy, C. Elif; Tasdelen, M. A.

    Organizations: Turkish Scientific and Technical Research Council (TUBITAK) [216Z060]; 1002-Short Term R&D Funding Program

    Keywords: functionalization of polymers; polyolefins; surfaces and interfaces

    Synthesis of fluorine containing polypropylene (PP Symbol of the Klingon Empire F) from chlorinated polypropylene (PP Symbol of the Klingon Empire Cl) via Cu(I) catalyzed Huisgen type 1,3-dipolar cycloaddition (CuAAC) and its water repellency properties are demonstrated. Initially, clickable azido-functional polypropylene (PP Symbol of the Klingon Empire N-3) and alkyne-functionalized fluorine compound (F Symbol of the Klingon Empire Al) are independently prepared by nucleophilic substitution of PP Symbol of the Klingon Empire Cl with azidotrimethylsilane-tetrabutylammonium fluoride and esterification reactions of 2,2,3,3,4,4,5,5-octafluoro-1-pentanol with 4-pentyonic acid. The CuAAC reaction between PP Symbol of the Klingon Empire N-3 and F Symbol of the Klingon Empire Al leads to corresponding PP Symbol of the Klingon Empire F under mild conditions. The chemical structures and surface properties of desired PP Symbol of the Klingon Empire F are characterized by Fourier transform infrared, H-1-NMR, differential scanning calorimetry, scanning electron microscopy, atomic force microscope, and contact angle analyses. Based on water contact angle (WCA) measurement, it is found that both PP Symbol of the Klingon Empire Cl and PP Symbol of the Klingon Empire N-3 films have shown similar hydrophobicity, whereas the WCA of PP Symbol of the Klingon Empire F is surprisingly decreased due to the presence of ester and triazole groups coming from F Symbol of the Klingon Empire Al compound and the clicked product. This facile modification procedure could be utilized in order to alter the wetting or thermal properties of the commercial polymers for potential applications. (c) 2018 Wiley Periodicals, Inc.
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