O. Ozarslan et al., NOVEL POLY(ARYLENE ETHER KETONE KETONE)S SYNTHESIZED BY FRIEDEL-CRAFTS ACYLATION, Macromolecular chemistry and physics, 199(9), 1998, pp. 1887-1893
A series of novel poly(arylene ether ketone ketone)s were prepared fro
m two novel oligomers and three different diacid chlorides via Friedel
-Crafts polymerization. The oligomers 2,6-bis(4-phenoxybenzoyl)naphtha
lene and 5-tert-butyl-1,3-bis(4-phenoxybenzoyl)benzene were synthesize
d by Friedel-Crafts acylation of diphenyl ether with 2,6-naphthalenedi
carbonyl dichloride and 5-tert-butylisophthaloyl dichloride, respectiv
ely, in the presence of AlCl3 as catalyst. Friedel-Crafts polymerizati
on of either of these two novel oligomers with tert-butylisophthaloyl
dichloride, isophthaloyl dichloride or 1,6-hexanedioyl dichloride gave
six novel PEKK's, having T-g's in the range of 135-180 degrees C, but
only the naphthalene-based PEKKs displayed T-m's between 130 and 345
degrees C. PEKK's containing the 5-tert-butylisophthaloyl group are so
luble in polar solvents such as N,N-dimethylacetamide, N-methyl-2-pyrr
olidone, N,N-dimethylformamide, THF, chloroform etc. Polymer PA(1), wh
ich has a fully unsubstituted aromatic chain structure, is insoluble i
n common organic solvents and, moreover, shows polymorphism. Intrinsic
viscosities and adhesion behavior of soluble PEKKs were also determin
ed.