2‐(4′‐Hydroxyphenylbenzoyl)benzoic acid is readily available from phenolphthalein by reaction with hydroxylamine. On treatment with hydrazine, 4‐(4‐hydroxyphenyl)phthalazin‐1‐one is formed in high yield. Under conditions conventionally used for the synthesis of poly(aryl ether)s the phthalazinone reacts with 4,4‐difluorobenzophenone or 4,4′‐difluorodiphenyl sulfone to yield high molecular weight linear polymers which are thermooxidatively stable and have Tg's approaching 300°C. The phthalazinone NH groups behave like phenolic OH groups and the resulting polymers contain O‐C and N‐C linkages. Phenyl‐substituted phenolphthaleins have also been synthesized and converted to the corresponding phthalazinone polymers.
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A linear, high molecular weight polyformal is readily synthesized by direct transformation of commercially available polycarbonate. The reaction is best carried out in dibromomethane with 8.0 equiv. of potassium hydroxide pellets in the presence of a phase‐transfer catalyst at 90–95°C. A random copoly(carbonate formal) can also be obtained simply by reducing the amount of potassium hydroxide used in the reaction. The molecular weight of the resulting polymer is governed by the starting polycarbonate.
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