Synthesis and properties of novel polyarylates and poly(ether ether ketone)s derived from 2,7-triptycenediol

Novel polyarylates are obtained by interfacial polycondensations of 9,10-dihydro-9,10-o-benzenoanthracene-1,5-diol (2,7-triptycenediol; TRIDO) with aromatic diacyl chlorides using benzyltriethylammonium chloride as a phase transfer catalyst. Inherent viscosity ranged from 0.29 to 0.51 dlg(-1). The glass transition temperatures (T(g)s) were 243-249 degrees C, and temperatures at 5% weight loss (T(d)s) were above 488 degrees C. These polyarylates were amorphous. The polyarylate derived from TRIDO and isophthaloyl dichloride showed good solubility in several organic solvents. Novel poly(ether ether ketone)s are prepared by nucleophilic displacement reaction of TRIDO with activated aromatic difluorides, such as 4,4'-difluorobenzophenone (DFBP) and 1,4-bis(4-fluorobenzoyl)benzene (BFBB), using potassium carbonate and toluene. Inherent viscosity ranged between 0.30-0.47 dig(-1). T(g)s were about 230 degrees C, and T(d)s from 544 to 568 degrees C. The poly(ether ether ketone) derived from TRIDO and DFBP (2c) possessed high solubility, and that from TRIDO and BFBB (2d) had poor solubility. X-Ray diffraction patterns suggested that 2e was amorphous and 2d was semi-crystalline. 2d melting point was 301 degrees C. A characteristic semi-crystalline nature was found only in poly(ether ether ketone) 2d even though aromatic polyamides, polyimides, and polyarylates containing 2,7-triptycenediyl structure were all amorphous.