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Synthesis and characterization of new diphenylfluorene‐based aromatic polyamides derived from 9,9‐bis[4‐(4‐carboxy‐phenoxy)phenyl]fluorene
Author(s) -
Hsiao ShengHuei,
Yang ChinPing,
Lin WeiLi
Publication year - 1999
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/(sici)1521-3935(19990601)200:6<1428::aid-macp1428>3.0.co;2-j
Subject(s) - fluorene , polymer chemistry , chemistry , ether , condensation polymer , pyridine , solvent , diphenyl ether , polyamide , dimethylformamide , nitrile , organic chemistry , alkaline hydrolysis , dimethylacetamide , hydrolysis , polymer
A new bis(ether‐carboxylic acid), 9,9‐bis[4‐(4‐carboxyphenoxy)phenyl]fluorene ( 3 ), was synthesized from the nucleophilic fluorodisplacement of p ‐fluorobenzonitrile with the dipotassium bisphenolate of 9,9‐bis(4‐hydroxyphenyl)fluorene, followed by alkaline hydrolysis of the intermediate bis(ether nitrile). A novel series of aromatic polyamides containing ether and bulky fluorenylidene groups were prepared by the direct polycondensation of the diacid 3 with various aromatic diamines in N ‐methyl‐2‐pyrrolidone (NMP) solution containing dissolved CaCl 2 using triphenyl phosphite and pyridine as condensing agents. The obtained polyamides have inherent viscosities in the range of 0.50–1.75 dL/g. All the polymers are readily soluble in a variety of organic solvents, such as NMP, N,N ‐dimethylacetamide (DMAc), N,N ‐dimethylformamide (DMF), and m ‐cresol, and afford transparent, flexible, and tough films by solvent casting. These polyamides have glass transition temperatures ranging from 200 to 303°C and show no significant weight loss up to 450°C, with 10% weight loss being recorded above 511°C in nitrogen or air.