New soluble, thermally stable poly(amide–imide)s containing cardo anthraquinone unit

Abstract

Preparation of new types of polyimides with high thermal stability and improved solubility was considered. In this way, two new amide diamines containing bulky pendant units were prepared in two steps: nucleophilic substitution reactions of 1- and 2-aminoanthraquinone with 3,5-dinitrobenzoyl chloride to form amide containing dinitro compounds, and then reduction of resulted dinitro compounds with hydrazine monohydrate in the presence of palladium/activated carbon. Two series of new poly(amide–imide)s were prepared from the reactions of these two diamines with various dianhydrides by one step polyimidation process. All poly(amide–imide)s were characterized by FTIR and 1H-NMR spectroscopies and elemental analysis. The polymers were obtained in high yields with inherent viscosities of 0.54–0.69 dl g −1. X-ray diffraction patterns (XRD) showed that all the polymers were amorphous and therefore this factor in addition to the introduction of bulky anthraquinone group led to good solubility of the polymers in most common organic solvents especially in N-methyl-2-pyrrolidone (NMP), N, N-dimethylacetamide (DMAc), N, N-dimethylformamide (DMF), and dimethylsulfoxide (DMSO). Thermal analysis showed glass transition temperature between 204 and 226 °C. Decomposition temperatures were more than 293 °C, also 10% weight loss were in the range of 387–419 °C in air.