Polyimides and Sulfonated Polyimides Derived from Functionalized 1,1‐Diphenylethylene Derivatives

Abstract

1,1‐Bis(4‐aminophenyl)ethylene was employed as a symmetrically disubstituted 1,1‐diphenylethylene monomer in the preparation of new polyimide derivatives by step growth polymerization methods with the introduction of the 1,1‐diphenylethylene unit along the polymer backbone. A series of 1,1‐diphenylethylene based polyimides were prepared via a two‐step polyimide synthesis process by the polycondensation reactions of 4,4′‐oxydiphthalic anhydride with different mole percentage ratios of 2,2‐bis[4‐(4‐aminophenoxy)phenyl]propane and 1,1‐bis(4‐aminophenyl)ethylene. Subsequent treatment of the appropriate polyimide derivative with sodium 3‐mercapto‐1‐propane sulfonate and AIBN via the thiol‐ene reaction outlines a new method for the synthesis of new sulfonated polyimide derivatives, with the alkyl sulfonate group introduced pendant to the polymer backbone. The organic compounds and the different polymer derivatives were characterized by dilute solution viscometry, 1H NMR and 13C NMR spectrometry, FTIR spectroscopy, thermogravimetric analysis, differential scanning calorimetry, atomic force microscopy and x‐ray diffraction measurements.