GB1158606A - New Polyglycidylethers, their preparation and their use - Google Patents

Abstract

1,158,606. Phthalimidines and polyglycidylethers of phthalimidines and oxindoles. CIBA Ltd. 22 Feb., 1967 [10 March, 1966], No. 8517/67. Heading C2C. [Also in Division C3] Novel compounds of the Formulµ I, II and III where Ri and R 1 <SP>1</SP> are hydrogen or C 1-4 alkyl, especially methyl, and R 2 represents, for Formula I, hydrogen, aliphatic, cycloaliphatic, araliphatic or aromatic hydrocarbons which may be substituted with hydroxy, ether, halo, epoxy, carboxy or ester substituents and for Formula III, C >2 alkyl, cycloalkyl, alkenyl, cycloalkenyl, aralkyl, epoxyalkyl, glycidyloxyalkyl, hydroxyalkyl, alkoxyalkyl, polyalkoxyalkyl, hydroxypolyalkoxyalkyl, cycloalkoxyalkyl, aryloxyalkyl, carboxyalkyl, alkoxycarbonylalkyl, cycloalkoxycarbonylalkyl, hydroxyalkoxycarbonylalkyl or aryloxycarbonylalkyl, are prepared by reacting suitably substituted phenolphthaleins with a primary amine of the formula R 2 -NH 2 , suitably at an elevated temperature, to give phthalimidines of Formula III and these phthalimidines or a corresponding isomeric oxindoles are reacted with epichlorohydrin or a glycerol dihalohydrin either in the presence of an alkali, suitably caustic soda or potash, or with LiCl, NaCl, a tertiary amine or a quaternary ammonium compound followed by a strong alkali, to give a compound of the Formula I or of the Formula II respectively. Under forcing conditions, see Example 12, phenolphthalimidine (III, R 1 , R 1 <SP>1</SP> and R 2 = H) reacts with epichlorohydrin to give N- glycidylphenolphthalimidine diglycidyl ether (I, R 1 , R 1 1 and R 2 = -O-CH 2 -CH-CH 2 -O).