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Synthesis and properties of polyimides derived from 1,4‐bis(4‐aminophenoxy)‐2‐(6‐oxido‐6 H ‐dibenz[ c,e ] [1,2]oxaphosphorin‐6‐yl) phenylene

2007; Wiley; Volume: 45; Issue: 14 Linguagem: Inglês

10.1002/pola.22046

1099-0518

Ching Hsuan Lin, Chun Hung Lin,

Silicone and Siloxane Chemistry

Abstract A new phosphorus‐containing aromatic diamine, 1,4‐bis(4‐aminophenoxy)‐2‐(6‐oxido‐6 H ‐dibenz[ c,e ] [1,2]oxaphosphorin‐6‐yl) phenylene ( 3 ) was synthesized by the nucleophilic aromatic substitution of 2‐(6‐oxido‐6 H ‐dibenz[ c,e ] [1,2]oxaphosphorin‐6‐yl)‐1,4‐dihydroxy phenylene ( 1 ) with 4‐fluoronitrobenzene, followed by catalytic hydrogenation. Light color, flexible, and creasable polyimides with high molecular weight, high glass transition, high thermal stability, improved organosolubility, and good oxygen plasma resistance were synthesized from the condensation of ( 3 ) with various aromatic dianhydrides in N , N ‐dimethylacetamide, followed by thermal imidization. The number‐average molecular weights of polyimides are in the range of 7.0–8.3 × 10 4 g/mol, and the weight‐average molecular weights are in the range of 12.5–16.5 × 10 4 g/mol. The T g s of these polyimides range from 230 to 304 °C by differential scanning calorimetry and from 228 to 305 °C by DMA. These polyimides are tough and flexible, with tensile strength at around 100 MPa. The degradation temperatures ( T d 5%) and char yields at 800 °C in nitrogen range from 544 to 597 °C and 59–65 wt %, respectively. Polyimides 5c and 5e , derived from OPDA and 6FDA, respectively, with the cutoff wavelength of 347 and 342 μm, respectively, show very light color. These polyimides also exhibit good oxygen plasma resistance. © 2007 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 45: 2897–2912, 2007