Synthesis and Characterization of Soluble and Thermally Stable Poly(ether–imide–urea)s

Two series of new modified poly(ether–imide–urea)s, POa–POc and PSa–PSc, with benzoxazole or benzothiazole pendent groups were successfully synthesized by diphenyl azidophosphate (DPAP)-activated one-pot polyaddition reaction of two bis(imide–dicarboxylic acid)s, 2-[3,5-bis(4-trimellitimidophenoxy)p...

Full description

Saved in:
Bibliographic Details
Published in:Bulletin of the Chemical Society of Japan 2014-05, Vol.87 (5), p.631-638
Main Author: Toiserkani, Hojjat
Format: Article
Language:English
Subjects:
Combustion
Diamines
Fourier transforms
Infrared spectroscopy
NMR spectroscopy
Polymers
Solubility
Thermal stability
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Two series of new modified poly(ether–imide–urea)s, POa–POc and PSa–PSc, with benzoxazole or benzothiazole pendent groups were successfully synthesized by diphenyl azidophosphate (DPAP)-activated one-pot polyaddition reaction of two bis(imide–dicarboxylic acid)s, 2-[3,5-bis(4-trimellitimidophenoxy)phenyl]benzoxazole (1O) or 2-[3,5-bis(4-trimellitimidophenoxy)phenyl]benzothiazole (1S) with various kinds of aromatic diamines a–c. In this direct method, the polymers were prepared by polyaddition reactions of the in situ-formed diisocyanate with the aromatic diamines. For comparative purposes, reference poly(ether–imide–urea)s, PRa–PRc, were also prepared by reacting a bis(imide–dicarboxylic acid) lacking pendent groups, namely, 3,5-bis(4-trimellitimidophenoxy)benzene (2) with the same diamines under similar conditions. Characterization of polymers was accomplished by inherent viscosity measurements, FTIR, 1H NMR spectroscopy and thermogravimetry. The polymers were obtained in quantitative yields with inherent viscosities between 0.19 and 0.37 dL g−1. The solubilities of modified poly(ether–imide–urea)s in common organic solvents as well as their thermal stability were enhanced compared to these of the corresponding unmodified poly(ether–imide–urea)s. The glass-transition temperature, 10% weight loss temperature, and char yields at 800 °C were, respectively, 7–28, 14–38 °C, and 3–7% higher than those of the reference polymers in nitrogen atmosphere.
ISSN:0009-2673
1348-0634
DOI:10.1246/bcsj.20130330