Synthesis, characterization, and thermal degradation of novel poly(2‐(5‐bromo benzofuran‐2‐yl)‐2‐oxoethyl methacrylate)

Abstract

A novel methacrylate monomer containing benzofuran side group, 2‐(5‐bromo benzofuran‐2‐yl)‐2‐oxoethyl methacrylate (BOEMA), was synthesized from esterification reaction of 2‐bromo‐1‐(5‐bromo benzofuran‐2‐yl) ethanone with sodium methacrylate at 85°C in the presence of 1,4‐dioxane solvent. After characterization with Fourier transform infrared spectrophotometer, nuclear magnetic resonance (1H‐NMR and 13C‐NMR), its homopolymerization was carried out by free radical polymerization at 60°C in the presence of benzoyl peroxide initiator and 1,4‐dioxane solvent. The glass transition temperature (Tg) of the synthesized novel polymer, poly(2‐(5‐bromo benzofuran‐2‐yl)‐2‐oxoethyl methacrylate) [poly(BOEMA)], was determined to be 137°C with differential scanning calorimetry technique. Thermal degradation kinetics of poly(BOEMA) was investigated by thermogravimetric analysis method at different heating rates with 5°C/min intervals between measurements. From dynamic measurements, the analysis of each process mechanism of Coats–Redfern and Van Krevelen methods showed that the most probable model for the decomposition process of poly(BOEMA) homopolymer agrees with the random nucleation, F1 mechanism. The apparent decomposition activation energies of poly(BOEMA) by Kissinger's and Flynn–Wall–Ozawa methods in the studied conversion range were 188.47 and 180.13 kJ/mol, respectively. POLYM. ENG. SCI., 2012. © 2011 Society of Plastics Engineers

Synthesis, Characterization and Thermal Decomposition Kinetics of a Novel Benzofuran Ketoxime Derived Polymer

“…The weight loss curves showed that decomposition of poly(BMKMA) took place in one stage in the 30% weight loss area attributed to the formation of volatile hydrocarbons in the first decomposition temperature range up to approximately 270 °C. 13 TGA curves and peak temperatures shift to higher values with an increase in the heating rate. This alteration has been recorded in the a) b) case of thermal degradation of different types of polymers.…”

“…13 In order to estimate the thermal degradation mechanism, these functions can be applied to thermogravimetry. 23 …”

“…[10][11][12] Some different benzofuran derivative polymers have been successfully synthesized in recent years. [13][14][15][16] In one of our previous studies, we synthesized and characterized a polymer containing benzofuran side group, poly(2-(5-bromo benzofuran-2-yl)-2-oxoethyl methacrylate), and we also investigated its thermal degradation kinetics. 13 In another study, Yonezumi and coworkers 14 studied the living cationic polymerization of benzofuran and some dihydrofurans using base-stabilized initiating systems with various Lewis acids.…”

“…[13][14][15][16] In one of our previous studies, we synthesized and characterized a polymer containing benzofuran side group, poly(2-(5-bromo benzofuran-2-yl)-2-oxoethyl methacrylate), and we also investigated its thermal degradation kinetics. 13 In another study, Yonezumi and coworkers 14 studied the living cationic polymerization of benzofuran and some dihydrofurans using base-stabilized initiating systems with various Lewis acids. Xu and coworkers 15 reported the electro-syntheses of poly(2,3-benzofuran) films in boron trifluoride diethyl etherate containing poly(ethylene glycol) oligomers and some properties.…”

Optical Properties of Poly(2-(5-bromo benzofuran-2-yl)-2-oxoethyl methacrylate)/Organoclay Nanocomposites

“…Pristine montmorillonite clay, Na-MMT, (cation exchange capacity, CEC = 119 meq/100 g) was purchased from Sigma-Aldrich. Poly(2-(5-bromo benzofuran-2-yl)-2-oxoethyl methacrylate), poly(BOEMA), was synthesized by free radical polymerization at 60 • C in the presence of benzoyl peroxide initiator and 1,4-dioxane solvent and characterized according to reference [36] as seen in Scheme 1.…”