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Synthesis of new alicyclic polyimides by Diels‐Alder polymerization
Author(s) -
Chi Jun Ho,
Shin Gyo Jic,
Kim Yong Seok,
Jung Jin Chul
Publication year - 2007
Publication title -
journal of applied polymer science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.575
H-Index - 166
eISSN - 1097-4628
pISSN - 0021-8995
DOI - 10.1002/app.26169
Subject(s) - alicyclic compound , arylene , polymerization , spectroscopy , polymer chemistry , nuclear magnetic resonance spectroscopy , materials science , solubility , amorphous solid , chemistry , polymer , organic chemistry , alkyl , physics , quantum mechanics , aryl
Abstract Four new alicyclic poly{arylene‐9,10‐di[4‐(methyloxy)phenyloxy]‐1,2,3,4,5,6,7,8‐octahydroanthracene‐2,3,6,7‐tetracarboxdiimide}s (APIs) were prepared at 80°C in the presence of NaI in DMSO by the in situ Diels‐Alder polymerization of 1,4‐bis[4‐(methyloxy)phenyloxy]‐2,3,6,7‐tetrakis(bromomethyl)benzene (MPBB) with four arylenebismaleimides (AMIs). The stereochemical isomerisms measured for the model compound DPAI and MDA‐PI by HETCOR spectroscopy and 1 H‐NMR spectroscopy, respectively, revealed that DPAI and APIs presumably have only one trans‐bis‐endo ‐configuration. Inherent viscosities of APIs varied in the 0.20–0.41 dL/g range. Solubility tests revealed that in spite of the alicyclic units incorporated the APIs were only marginally soluble in polar organic solvents. In TGA in N 2 the APIs began to decompose at temperatures higher than 380°C, revealing two‐step pyrolysis behavior. 4‐(Methyloxy)phenyloxy side groups were believed to degrade in the lower temperature range. In DSC and wide‐angle X‐ray diffractometry APIs all appeared completely amorphous and in UV‐Vis spectroscopy both DPAI and APIs were transparent at wavelengths longer than 375 nm. © 2007 Wiley Periodicals, Inc. J Appl Polym Sci 2007