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Synthesis And Characterization Of Polytriazole Containing 2,6-diphenylpyridine And Trifluoromethyl Groups

Posted on:2016-08-29Degree:MasterType:Thesis
Country:ChinaCandidate:C FangFull Text:PDF
GTID:2271330470460023Subject:Polymer Chemistry and Physics
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As a high yield, mild processing and high selectivity method in polymer chemistry, click polymerization has been greatly developed and widely used in nanoparticles,photoelectric materials, bio-materials and some novel fields. Linear poly(triazole)s(PTAs), due to its worse solubility and melt, it is difficult for researcher to characterize, process and even to apply for industry. In my dissertation, I focus to design a new monomer, which contained 2,6–diphenylpyridine groups in the main chain and trifluoromethyl in the side chain, to synthesis three kinds of novel polymers.Then we have some characterizations. The main works include the following three parts:1. The 2,6-Bis-(4-phenol)-4-(4-trifluoromethyl-phenyl)-pyridine(MPHPP), was success-fully prepared from a modified Chichibabin reaction of4-Trifluoromethyl-benzaldehyde and 1-(4-trifluoromethyl-phenyl)-ethanone,and then reacted with 3-bromo-propyne. And the 2,6-Bis-(4-prop-2-ynyloxyphenyl)-4-(4-trifluoromethyl-phenyl)-pyridine(PYOPMPP) was obtained. By this routine, we get a excellent yield. The Ar(N3)2 was obtained by the reaction of aromatic diamine and Na N3. Furthermore, the polymerization of Ar(N3)2 and PYOPMPP was happened in the solvent of dry DMAc in 90°C. A series of PTAs obtained were soluble in dipolar solvent such as DMSO, DMAc, NMP. The inherent viscosities of the PTA ranged from 0.45–0.67 d L/g. The glass transition temperature of those ranged from 182 to 223°C and the decomposition temperature at 5% weight ranged from 285 to 307°C. Furthermore, PTAs exhibited outstanding solubility and thermal stability. In addition, the PTAs films exhibited good optical transparency and low moisture uptakes of 0.94–1.01 %.However, it showed not the great mechanical properties.2. Similarly, the symmetric of Ar(NH2)2 was obtained by the reaction of the symmetric Ar(OH)2 and 2-chloro-5-nitro-benzotrifluoride and the reduction of the resulting dinitro compound. And then, The Ar(N3)2 was obtained by the reaction of aromatic diamine and Na N3. Furthermore, the polymerization of Ar(N3)2 and PYOPMPP was happened in the solvent of dry DMAc, A series of PTAs obtained were soluble in dipolar solvent such as DMSO, DMAc, NMP,and also in a less efficient solvent such as THF and pyridine.The inherent viscosities of the PTAs ranged from 0.54 to 0.66 d L/g. The glass transition temperature of those ranged from 200 to 219°C and the decomposition temperature at 5% weight ranged from 283 to 311°C. Furthermore, PTAsexhibited outstanding solubility and thermal stability. In addition, the PTAs films exhibited good optical transparency and low moisture uptakes.3. The ryridine-based dinitro compound, 4-(4-tifluomethylphenyl)-2,6-bis(4-nitrophenyl) pyridine(MPNPP), was successfully prepared from a modified Chichibabin reaction of 4-nitroacetophenone and 4-trifluoromethyl benzaldehyde.1,4-bis(4-amino-2-trifluoro methylphenoxy)benzene(MPAPP), was synthesized by a nitro reduction of 1,4-bis(4- nitro-2-trifluoromethylphenoxy), which was acquired by reacting hydroquinone with 2-chloro-5-nitrobenzotrifluoride. The2,6-Bis-(4-azido-phenyl)-4-(4-trifluoromethyl-phenyl)-pyridine(APMPP) was obtained by the reaction of MPAPP and Na N3. The aromatic diynes was obtained by the reaction of aromatic diphenols and 3-bromo-propyne.Furthermore, the polymerization of aromatic diynes and APMPP was happened in the solvent of dry DMAc. A series of PTAs obtained were soluble in dipolar solvent such as DMSO, DMAc, NMP. The glass transition temperature of those ranged from 192 to 225°C and the decomposition temperature at 5% weight ranged from 303 to 324°C. Furthermore, PTAs exhibited outstanding solubility and thermal stability. In addition, the PTAs films exhibited good optical transparency and low moisture uptakes.
Keywords/Search Tags:poly(triazole)s, 2,6–diphenylpyridine groups, trifluoromethyl, 2,6-Bis-(4-prop-2-ynyloxy-phenyl)-4-(4-trifluoromethyl-phenyl)-pyridine, 2,6-Bis-(4-azido-phenyl)-4-(4-trifluoromethyl-phenyl)-pyridine, synthesis and characterization
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