Synthesis of fluorinated polypropylene using CuAAC click chemistry

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.

Polypropylene microfibers via solution electrospinning under ambient conditions

“…The SEM images of some resulted fibers at 250 and 1000× magnifications and the photographs of the water droplets on the fiber surfaces have presented in Figures (a–e) to provide an assessment of the surface properties (Table ). In our recent study, contact angle value of the water was measured as 102° ± 2.0 on flat PP‐Cl film prepared by simple dipping method . Electrospinning process is known as an incentive technique in order to enhance hydrophobicity of the surfaces with low surface energies .…”

Synthesis, properties and enzymatic biodegradation behavior of fluorinated poly(ε-caprolactone)s

“…In this figure, the peaks at 2935, 1725, and 1175 cm -1 have been associated with the -CH stretching, >C=O stretching and etheric C-O stretching vibrations, respectively. Meanwhile, in the zoomed image of this figure, one may notice that -CF 2 stretching vibration peaks at 1145 and 1110 cm -1 [9]. These findings from FT-IR analysis indicate that the success of ring-opening polymerizations by using OFP.…”

“…In the 1 H-NMR spectra of F-PCLs, the characteristic methylene protons of -CH 2 -CH 2 -CH 2 -O-, (C=O)-CH 2 -CH 2 , -CH 2 -CH 2 -O-and (C=O)-CH 2 groups detected at 1.36 ppm (e), 1.63 ppm (d+f), 2.28 ppm (c) and 4.04 ppm (g) were corresponded to the PCL repeating unit in F-PCLs. Furthermore, methylene protons of CH 2 -C=O group and methine proton of CH-F 2 group appeared at 4.57 ppm (b), and 5.93-6.15 ppm (a) were attributed to OFP moieties [9,21]. On the other hand, as can be seen in 19 F-NMR spectra of F-PCLs, the peaks of CHF 2 , CHF 2 -CF 2 , CHF 2 -CF 2 -CF 2 , CHF 2 -CF 2 -CF 2 -CF 2 groups seemed at -137,28 ppm (w), -130.02 ppm (x), -125,37 ppm (y) and -119,74 ppm (z), respectively, coming from OFP moieties supported the formation of targeted fluorinated polymers [26].…”

“…The synthesis of fluorinated polymers is a topic of great interest in the biomaterial industry due to their distinctive characteristics such as water and oil repellency, high thermal, weather and chemical stability, low dielectric constant, low coefficient of friction, flame retardancy, and low surface energy [8]. Basically, there are two ways in the literature for the synthesis of fluorinated polymers; either direct polymerization of fluorinated monomers or introducing fluorinated moieties into the polymer chain using well-known chemical reactions [9]. Due to those of afore-mentioned reasons, they have been widely utilized in diverse applications, including chemistry [10], textiles [11], automotive [12], energy [13], bacterial coatings [14], and biomedical [15] fields.…”

A Brief Minireview of poly-triazole: Alkyne and Azide Substrate Selective, Metal-catalyst Design

“…11,12 Along with high regioselectivity, carbon atoms are coordinated on the electron cloud density change without end group of copper ion catalytic acetylene and azide. 13,14 In most cases, the 3-dipole ring addition reaction is not regionally selective and the reaction is slow. 15,16 Biomolecules have hardly reacted with azide and alkyne group, due to the weak polarity of the latter two ones.…”