Bisphenol A polycarbonate (BPA-PC) is a remarkable high-performance
engineering polymer, although it is susceptible to photo-Fries and
hydrolytic degradation. New poly(aryl ether carbonates) were synthesized
to address these limitations by replacing the chain backbone carbonate
ester functionality with aryl ether functionality. The monomers for
these new polymers were synthesized by a variation of the Ullmann
condensation accelerated by 2,2,6,6-tetramethylheptane-3,5-dione and
promoted by Cs2CO3 and 1-methyl-2-pyrrolidinone
under mild conditions. Four such bisphenol A-based diarylether monomers
containing different mass ratios of carbonate ester groups were prepared
and polymerized with phosgene gas to give novel poly(aryl ether carbonates).
Polymers were named as di-o-BPA-PC 9′, tri-o-BPA-PC 11′, tetra-o-BPA-PC 13′, and penta-o-BPA-PC 15′ where di-, tri-, tetra-, and penta-
reflect the number of diphenylisopropylidene units in each of the
respective polymers. The molecular weights of the resulting four poly(aryl
ether carbonates) were measured by gel permeation chromatography.
Differential scanning calorimetry was used to measure glass transition
temperature (Tg). The polymers exhibited
weight-average molecular weights up to 4.09 × 105 g/mol
and Tg in the range of 136 to 149 °C
with no melting temperature peak, indicative of their amorphous character.
The new polymers formed transparent and flexible films by solution
casting from chloroform solution.
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