Gc. Eastmond et J. Paprotny, SYNTHESIS OF BIS(ETHER ANHYDRIDE)S FOR POLY(ETHER IMIDE)S HAVING 1,2-LINKED UNITS BY NITRODISPLACEMENT WITH CATECHOL DERIVATIVES, Macromolecules, 28(7), 1995, pp. 2140-2146
This paper extends a recent announcement that catechol will undergo ni
trodisplacement with 4-nitrophthalonitrile to form a bis(ether dinitri
le) to a series of substituted catechols and to reaction with 3-nitrop
hthalonitrile. For all catechols studied the bis(ether dinitrile)s wer
e readily hydrolyzed to bis(ether diacid)s and converted to bis(ether
anhydride)s. The bis(ether anhydride)s were converted to high-molecula
r-weight polymers with bis(4-aminophenyl) ether in solution polymeriza
tion with chemical imidization. The polymers formed have lower glass t
ransition temperatures than polymers based on the hydroquinone-based b
is(ether anhydride) and have far greater solubilities and processabili
ty than corresponding polymers based on hydroquinone and resorcinol-ba
sed bis(ether anhydride)s.