Soluble high‐<i>T</i>_g polyetherimides with good flame retardancy based on an asymmetric phosphinated etherdiamine

Abstract

Abstract This study focuses on preparing soluble, high‐ T g polyetherimides (PEIs) with good flame retardancy. To achieve this goal, a phosphinated aminophenol, 1‐(4‐hydroxyphenyl)‐1‐(4‐aminophenyl)‐1‐(6‐oxido‐6H‐dibenz〈c,e〉〈1,2〉oxaphosphorin‐6‐yl)ethane ( 1 ), was prepared. Then, an asymmetric etherdiamine, 1‐(4‐(4‐aminophenoxy)phenyl)‐1‐(4‐aminophenyl)‐1‐(6‐oxido‐6H‐dibenz〈c,e〉〈1,2〉oxaphosphorin‐6‐yl)ethane ( 3 ), was prepared from the nucleophilic substitution of ( 1 ) with 4‐chloronitrobenzene, followed by catalytic hydrogenation. Light colored, tough, and foldable PEIs ( 5 ) with good thermal stability, organo‐solubility, and good flame retardancy were synthesized from the condensation of ( 3 ) with various aromatic dianhydrides in N , N ‐dimethylacetamide, followed by thermal imidization. Properties of the resulting PEIs were evaluated and compared with those of symmetric PEIs ( 5 ′) and polyimides ( 5 ″). The structure–property relationships were discussed. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011