Synthesis of fluorinated polypropylene using CuAAC click chemistry

Abstract

ABSTRACT Synthesis of fluorine containing polypropylene (PPF) from chlorinated polypropylene (PP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N 3 ) and alkyne‐functionalized fluorine compound (FAl) are independently prepared by nucleophilic substitution of PP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N 3 and FAl leads to corresponding PPF under mild conditions. The chemical structures and surface properties of desired PPF 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 PPCl and PPN 3 films have shown similar hydrophobicity, whereas the WCA of PPF is surprisingly decreased due to the presence of ester and triazole groups coming from F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. © 2018 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2019 , 136 , 47072.