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Synthesis of fluorinated polypropylene using CuAAC click chemistry
Author(s) -
Acik G.,
Cansoy C. Elif,
Tasdelen M. A.
Publication year - 2019
Publication title -
journal of applied polymer science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.575
H-Index - 166
eISSN - 1097-4628
pISSN - 0021-8995
DOI - 10.1002/app.47072
Subject(s) - contact angle , polypropylene , click chemistry , differential scanning calorimetry , wetting , polymer chemistry , cycloaddition , nucleophile , materials science , fourier transform infrared spectroscopy , nucleophilic substitution , polymer , chemistry , chemical engineering , organic chemistry , catalysis , composite material , physics , engineering , thermodynamics
Synthesis of fluorine containing polypropylene (PPF) from chlorinated polypropylene (PPCl) via Cu(I) catalyzed Huisgen type 1,3‐dipolar cycloaddition (CuAAC) and its water repellency properties are demonstrated. Initially, clickable azido‐functional polypropylene (PPN 3 ) and alkyne‐functionalized fluorine compound (FAl) are independently prepared by nucleophilic substitution of PPCl 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 PPN 3 and FAl leads to corresponding PPF under mild conditions. The chemical structures and surface properties of desired PPF are characterized by Fourier transform infrared, 1 H‐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 PPCl and PPN 3 films have shown similar hydrophobicity, whereas the WCA of PPF is surprisingly decreased due to the presence of ester and triazole groups coming from FAl 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. © 2018 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2019 , 136 , 47072.