Poly(ether ether sulfone)s and sulfonated poly(ether ether sulfone)s derived from functionalized 1,1‐diphenylethylene derivatives

Abstract

The preparation of a series of thermally stable poly(ether ether sulfone) derivatives from functionalized 1,1‐diphenylethylene derivatives, with the random introduction of the 1,1‐diphenylethylene unit along the polymer backbone, is reported. The post‐polymerization thiol‐ene addition reaction of the 1,1‐diphenylethylene unit of the poly(ether ether sulfone) precursor with sodium 3‐mercapto‐1‐propane sulfonate affords a new, well‐defined sulfonated poly(ether ether sulfone) derivative, with the alkyl sulfonate group introduced pendant to the polymer backbone.

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

“…The preparation of sulfonated polyimide derivatives via post‐polymerization sulfonation reactions has been reported in the literature . In addition, the post‐polymerization sulfonation reactions of engineering polymers mediated by the thiol‐ene reaction with sites of unsaturation along the polymer backbone or pendant to the backbone affords sulfonated polymers with the introduction of the functional group along the polymer backbone. However, the preparation of sulfonated polyimides with the alkyl sulfonate group pendant to the polymer backbone by post‐polymerization reaction mediated by the thiol‐ene reaction of thiols with appropriate polyimides derivatives has not been reported in the literature.…”

“…2,2‐Bis[4‐(4‐aminophenoxy)phenyl]propane ( 2 ) was dried in the oven at 60 °C for 12 hours to give 2,2‐bis[4‐(4‐aminophenoxy)phenyl]propane ( 2 ) as white solid with a melting point of 127–130 °C . AIBN (Eastman Chemical Company, Johannesburg, South Africa) was purified by recrystallization from ethanol at 50 °C …”

“…A new sulfonated polyimide derivative SPI‐2 , with the alkyl sulfonic acid group introduced pendant to the polymer chain, was prepared by the general procedure for the thiol‐ene reaction as outlined by Summers and coworkers and Guan and coworkers . In a typical procedure, sulfonated polyimide, SPI‐2 was prepared according to the following method.…”

“…Moreover, functionalized 1,1‐diphenylethylene derivatives have been employed as functionalizing agents in anionic polymerization reactions, atom transfer radical polymerization processes for the synthesis of functionalized polymers. In addition, the symmetrically functionalized 1,1‐diphenylethylene derivatives have been used as monomers in step growth polymerization methods for the preparation of engineering polymers with the 1,1‐diphenylethylene unit along the polymer backbone . The 1,1‐diphenylethylene based polymeric derivatives can be employed as substrates for post‐polymerization modification reactions via UV reactions for the improvement of the mechanical properties of the engineering polymers or the introduction of functional groups pendant to the polymer chain by standard organic reactions …”

“…The poly(amic acid) intermediates were produced at room temperature after 24 hours and were cast on a glass plate and then subjected to a thermal imidization process for 3 hours to produce the corresponding polyimides films. The 1,1‐diphenylethylene based polyimide derivatives were employed as substrates for the introduction of the alkyl sulfonic acid group along the polymer chain via the thiol‐ene reaction . Treatment of the appropriate polyimide derivative with sodium 3‐mercapto‐1‐propane sulfonate and AIBN via the thiol‐ene reaction outlines a new synthesis method for the preparation of new sulfonated polyimide derivatives, with the introduction of the alkyl sulfonic acid group pendant to the polymer backbone.…”