Synthesis and Characterization of Organosoluble, Thermal Stable and Hydrophobic Polyimides Derived from 4-(4-(1-Pyrrolidinyl)phenyl)-2,6-bis(4-(4-aminophenoxy)phenyl)pyridine

Abstract

A novel aromatic diamine monomer, 4-(4-(1-pyrrolidinyl)phenyl)-2,6-bis(4-(4-aminophenoxy)phenyl)pyridine (PPAPP) containing pyridine rings, pyrrolidine groups, and ether linkages, was successfully synthesized using 4-hydroxyacetophenone and 1-chloro-4-nitrobenzene as starting materials by three-step reactions, and then used to synthesize a series of polyimides by polycondensation with various aromatic dianhydrides via a two-step method. The structure of PPAPP was characterized by NMR, FT-IR, and mass spectrometry analysis methods. These polymers showed good solubility in common organic solvents (e.g., NMP, DMF, DMSO, and DMAc) at room temperature or on heating. Moreover, they presented a high thermal stability with the glass transition temperature ( T _gs) exceeding 316 °C, as well as the temperature of 10% weight loss ranged from 552 to 580 °C with more than 67% residue at 800 °C under nitrogen. Furthermore, they also exhibited excellent hydrophobicity with a contact angle in the range of 85.6° to 97.7°, and the results of Wide-Angle X-ray Diffraction (WAXD) indicated that all of the polymers revealed an amorphous structure.