SYNTHESIS OF BIS(ETHER ANHYDRIDE)S FOR POLY(ETHER IMIDE)S HAVING 1,2-LINKED UNITS BY NITRODISPLACEMENT WITH CATECHOL DERIVATIVES

This paper extends a recent announcement that catechol will undergo nitrodisplacement with 4-nitrophthalonitrile to form a bis(ether dinitrile) to a series of substituted catechols and to reaction with 3-nitrophthalonitrile. For all catechols studied the bis(ether dinitrile)s were readily hydrolyzed to bis(ether diacid)s and converted to bis(ether anhydride)s. The bis(ether anhydride)s were converted to high-molecular-weight polymers with bis(4-aminophenyl) ether in solution polymerization with chemical imidization. The polymers formed have lower glass transition temperatures than polymers based on the hydroquinone-based bis(ether anhydride) and have far greater solubilities and processability than corresponding polymers based on hydroquinone and resorcinol-based bis(ether anhydride)s.