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Synthesis and properties of novel soluble polyimides having an unsymmetric spiro tricyclic dianhydride unit
Author(s) -
Li Jun,
Kato Jun,
Kudo Kazuaki,
Shiraishi Shinsaku
Publication year - 2000
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 - 10.1002/1521-3935(20001101)201:17<2289::aid-macp2289>3.0.co;2-f
Subject(s) - alicyclic compound , polymer chemistry , pyromellitic dianhydride , polymerization , glass transition , tetrahydrofuran , chemistry , acetic anhydride , materials science , organic chemistry , polymer , polyimide , catalysis , layer (electronics) , solvent
Abstract A novel spiro trialicyclic dianhydride, rel [1 S ,5 R ,6 R ]‐3‐oxabicyclo[3.2.1]octane‐2,4‐dione‐6‐spiro‐3′‐(tetrahydrofuran‐2′,5′‐dione) ( DAn ) was synthesized from itaconic anhydride ( 1 ) and cyclopentadiene via a Diels‐Alder reaction, nitric acid oxidation, and the subsequent dehydration with acetic anhydride. The structure of DAn was determined by NMR spectra and single crystal X‐ray diffraction. A series of soluble polyimides ( PI s) having a spiro alicyclic unit in the main chain were prepared by the reactions of DAn with several diamines through a general two‐step polymerization method. Polymerization temperature affected inherent viscosities of poly(amic acid)s. Chemically imidized PI s had the inherent viscosities in the range of 0.10–0.49 dL/g. Due to the unsymmetric spiro alicyclic structure, the PI s showed excellent solubility in many organic solvents. Glass transition temperatures of PI s ranged from 215 to 279°C and some of them showed no glass transition temperature. The 10% weight loss temperatures under nitrogen were in a range of 355–430°C. Films of PI s obtained by the thermal imidization were wholly transparent and colorless.