ISSN:
0025-116X
Keywords:
Chemistry
;
Polymer and Materials Science
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
,
Physics
Notes:
Three active p-aminobenzenesulfonic acid derivatives, 1-(p-aminobenzenesulfonyl)imidazole (4a), 1-(p-aminobenzenesulfonyloxy)benzotriazole (4b), and 2-phenyl-4-(p-aminobenzenesulfonyl)-1,3,4-oxadiazoline-5-thione (4c) were synthesized by reacting p-isocyanatobenzenesulfonyl chloride (1) with stoichiometrical quantities of water in the presence of dibutyltin didodecanoate and subsequently with imidazole, 1-hydroxybenzotriazole and 2-phenyl-1,3,4-oxadiazoline-5-thione, respectively. The self-polycondensation of 4a-c, leading to poly(p-benzenesulfonamide) (7), was carried out in solution using polar aprotic solvents, N-methyl-2-pyrrolidone (NMP) and hexamethylphosphoric triamide (HMPA), and acidic media, dimethyl sulfoxide (DMSO) and m-cresol, with or without an appropriate acid catalyst or acid acceptor under mild conditions. Poly(p-benzenesulfonamide) having the highest reduced viscosity of 0,14 dl·-1 was obtained almost quantitatively from 4c by using m-cresol as a solvent without any acid catalyst and acid acceptor at 25°C. The polymers are soluble in polar aprotic solvents such as NMP, HMPA and DMSO and in aqueous sodium hydroxide. These poly(p-benzenesulfonamide)s are less thermally stable than completely aromatic polyamides, because the initial weight-loss started at 250-350°C. Aminolysis of three benzenesulfonic acid derivatives, 1-benzenesulfonylimidazole (5a), 1-benzenesulfonyloxybenzotriazole (5b), and 2-phenyl-4-benzenesulfonyl-1,3,4-oxadiazoline-5-thione (5c), with the same leaving groups was also carried out as a model reaction of self-polycondensation to determine the reaction conditions.
Additional Material:
2 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/macp.1987.021881206
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