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Specialty polyurethane soft segments. IV. Reactions of aminated poly(propylene glycols) with isatoic anhydride
Author(s) -
Harris Robert F.,
Lopez Karen M.
Publication year - 1993
Publication title -
journal of applied polymer science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.575
H-Index - 166
eISSN - 1097-4628
pISSN - 0021-8995
DOI - 10.1002/app.1993.070500401
Subject(s) - polyurethane , chemistry , amine gas treating , polymer , polymer chemistry , amide , organic chemistry , urea , propylene oxide , yield (engineering) , materials science , copolymer , ethylene oxide , metallurgy
Although it has been reported that aminated poly(propylene glycols) react with isatoic anhydride to cleanly yield the corresponding o ‐aminophenyl amide ( II ), this paper shows that a competing reaction leads to the formation of about 10% of the corresponding urea carboxylic acid ( III ). This impurity (unreactive toward polyisocyanates) limits the use‐fulness of ( II ) in urethane/urea polymers. A procedure has been developed to quantify ( II ) and ( III ). Based on the insight gained, a process has been developed to produce the corresponding o ‐aminophenyl amide derivatives of aminated poly(propylene glycols) in a state of high purity (˜100%). A given aminated poly(propylene glycol) is added dropwise to a siurry of isatoic anhydride in an inert fluid (such as toluene or a previously prepared product) at a temperature (60–100°C) at which reaction is rapid. Local excesses of unreacted amine are minimized to prevent formation of urea carboxylic acid impurities. This process has been applied to the preparation of the corresponding derivatives of a variety of aminated poly(propylene glycols). © 1993 John Wiley & Sons, Inc.