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Synthesis, characterization, and properties of semifluorinated organo‐soluble new aromatic polyamides
Author(s) -
Bera Debaditya,
Dasgupta Barnali,
Chatterjee Shyambo,
Maji Samarendra,
Banerjee Susanta
Publication year - 2012
Publication title -
polymers for advanced technologies
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.61
H-Index - 90
eISSN - 1099-1581
pISSN - 1042-7147
DOI - 10.1002/pat.1825
Subject(s) - isophthalic acid , trifluoromethyl , polymer chemistry , glass transition , tetrahydrofuran , differential scanning calorimetry , materials science , condensation polymer , dimethylformamide , polyamide , ether , thermal stability , organic chemistry , polymer , chemistry , polyester , terephthalic acid , solvent , alkyl , physics , thermodynamics
A series of organo‐soluble new polyamides were synthesized by the direct polycondensation of different semifluorinated aromatic diamines, namely 4,4‐bis[3'‐trifluoromethyl‐4'(4“‐amino benzoxy)benzyl]biphenyl; 4,4”‐bis(aminophenoxy)‐3'3“‐trifluoromethyl terphenyl; 1,3‐bis[3'‐trifluoromethyl‐4'(4”‐amino benzoxy)benzyl]benzene; 2,6‐bis(3'‐trifluoromethyl‐ p ‐aminobiphenyl ether)pyridine; and 2,5‐bis(3'‐trifluoromethyl‐ p ‐aminobiphenyl ether)thiophene with 5‐ t ‐butyl‐isophthalic acid. The polymers were fully characterized by elemental analysis and IR, NMR spectroscopies. The synthesized polyamides were soluble in several organic solvents such as 1‐methyl‐2‐pyrrolidone, N,N ‐dimethylformamide, N,N ‐dimethylacetamide, tetrahydrofuran, and dimethyl sulfoxide at room temperature. They showed inherent viscosities of 0.42–0.63 dl/g. The polyamides exhibited weight‐average molecular weights of up to 233,000, which depended on the exact repeating unit structure. The polyamides synthesized from 4,4‐bis[3'‐trifluoromethyl‐4'(4”‐amino benzoxy)benzyl]biphenyl and 5‐ t ‐butyl isophthalic acid exhibited highest glass‐transition temperatures 261°C (evaluated by differential scanning calorimetry) in nitrogen. These polyamides showed good thermal stability up to 475°C for a 10% weight loss in air. The polyamides films were clear and flexible in nature with tensile strengths of up to 88 MPa, modulus of elasticity of up to 1.81 GPa, and elongations at break of up to 25%, which depended on the exact repeating unit structure. X‐ray diffraction measurements indicated that these polyamides were amorphous in nature. Copyright © 2010 John Wiley & Sons, Ltd.