Soluble high-Tg polyetherimides with good flame retardancy based on an asymmetric phosphinated etherdiamine

• Published in: Journal of polymer science. Part A, Polymer chemistry Polymer chemistry, 2011-03, Vol.49 (6), p.1331-1340
• Main Authors: Lin, Ching Hsuan, Chang, Sheng Lung, Cheng, Po Wen
• Format: Article
• Language: English
• Subjects: Aminophenol; Applied sciences; asymmetric; Asymmetry; Condensing; Dianhydrides; Exact sciences and technology; Hydrogenation; Organic polymers; phosphinate; Physicochemistry of polymers; Polyetherimides; Polyimide resins; polyimides; Polymers with particular properties; Preparation, kinetics, thermodynamics, mechanism and catalysts; Reproduction; solubility; structure-property relationship
• ISSN: 0887-624X; 1099-0518; 1099-0518
• DOI: 10.1002/pola.24552

This study focuses on preparing soluble, high-Tg 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.