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Oligo(ether‐sulfones), 2 . Synthesis of a novel macrocyclic aromatic ether sulfone bearing two carboxylic groups and the corresponding polyamide via direct condensation of the macrocycle with 4,4′‐diaminodiphenylmethane
Author(s) -
Rodewald Barbara,
Ritter Helmut
Publication year - 1997
Publication title -
macromolecular rapid communications
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.348
H-Index - 154
eISSN - 1521-3927
pISSN - 1022-1336
DOI - 10.1002/marc.1997.030180910
Subject(s) - sulfone , ether , carboxylic acid , polymer chemistry , polyamide , chemistry , diamine , arylene , organic chemistry , aryl , alkyl
A new macrocyclic arylene ether sulfone bearing two carboxylic groups, 4 , was prepared by use of pseudo high dilution techniques. In a first step, 4,4‐bis[4‐(4‐(4‐chlorophenylsulfonyl)phenoxy)phenyl]pentanoic acid ( 3 ) was prepared from bis(4‐chlorophenyl)sulfone ( 1 ) and an excess of 4,4‐bis(4‐hydroxyphenyl)pentanoic acid ( 2 ). Then, the purified trimer 3 was cyclocondensed with 4,4‐bis(4‐hydroxyphenyl)pentanoic acid ( 2 ), yielding the bifunctionalized macrocycle 4 . The existence of the ring‐shaped molecule was proved by use of MALDI‐TOF, NMR‐ and IR‐spectroscopy. The free carboxylic groups of 4 were used to build up polyamides that contain the macrocycle in the main chain and 4,4′‐diaminodiphenylmethane ( 5 ) as an aromatic diamine.