Polymer, Vol.46, No.25, 11986-11993, 2005
Synthesis and properties of novel polyimides derived from 2,6-bis(4-aminophenoxy-4'-benzoyl)pyridine with some of dianhydride monomers
A new kind of aromatic diamine monomer containing pyridine unit, 2,6-bis(4-aminophenoxy-4 '-benzoyl)pyridine (BABP), was synthesized successfully. The Friedel-Crafts acylation of phenyl ethyl ether with 2,6-pyridinedicarbonyl chloride formed 2,6-bis(4,4 '-dihydroxybenzoyl)-pyridine (BHBP), BHBP was changed into 2,6-bis(4-nitrophenoxy-4'-benzoyl)-pyridine (BNBP) by the nucleophilic substitution reaction of it and p-chloronitrobenzene, and BNBP was reduced with SnCl, and HCl in ethanol to form the diamine monomer BABP finally, the diamine monomer BABP could be obtained in quantitative yield. A series of novel polyimides were prepared by polycondensation of BABP with various aromatic dianhydrides in N-methy-2-pyrrolidone (NMP) via the conventional two-step method. Experimental results indicated that some of the polyimides were soluble both in strong dipolar solvents (N-methy-2-pyrrolidone or N,N-dimethylacetamide) and in common organic solvents tetrahydrofuran. The resulting polyimides showed exceptional thermal and thermooxidative stability, no weight loss was detected before a temperature of 450 degrees C in nitrogen, and the values of glass-transition temperature of them were in the range of 208-324 degrees C. Wide-angle X-ray diffraction measurements revealed that these polyimides were predominantly amorphous. (c) 2005 Elsevier Ltd. All rights reserved.