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Novel poly(arylene ether ketone ketone)s synthesized by Friedel‐Crafts acylation
Author(s) -
Özarslan Özdemir,
Yildiz Emel,
Yilmaz Tülay,
Güngör Attila,
Kuyulu Abdülkadir
Publication year - 1998
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/(sici)1521-3935(19980901)199:9<1887::aid-macp1887>3.0.co;2-n
Subject(s) - arylene , ketone , friedel–crafts reaction , ether , chemistry , polymer chemistry , acylation , dimethylformamide , polymerization , condensation polymer , organic chemistry , polymer , catalysis , solvent , alkyl , aryl
A series of novel poly(arylene ether ketone ketone)s were prepared from two novel oligomers and three different diacid chlorides via Friedel‐Crafts polymerization. The oligomers 2,6‐bis(4‐phenoxybenzoyl)naphthalene and 5‐ tert ‐butyl‐1,3‐bis(4‐phenoxybenzoyl)benzene were synthesized by Friedel‐Crafts acylation of diphenyl ether with 2,6‐naphthalenedicarbonyl dichloride and 5‐ tert ‐butylisophthaloyl dichloride, respectively, in the presence of AlCl 3 as catalyst. Friedel‐Crafts polymerization 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°C, but only the naphthalene‐based PEKKs displayed T m 's between 130 and 345°C. PEKK's containing the 5‐ tert ‐butylisophthaloyl group are soluble in polar solvents such as N , N ‐dimethylacetamide, N ‐methyl‐2‐pyrrolidone, N , N ‐dimethylformamide, THF, chloroform etc. Polymer PA 1 , which has a fully unsubstituted aromatic chain structure, is insoluble in common organic solvents and, moreover, shows polymorphism. Intrinsic viscosities and adhesion behavior of soluble PEKKs were also determined.