GB1032884A - Epoxide adducts of phenyl-arylamine-aldehyde condensation products - Google Patents

Abstract

The invention relates to vicinal epoxide adducts of uncatalysed condensation products produced from a phenol, an aromatic amine and an aldehyde. Specified phenols from which the condensation products may be derived are phenol, alkylphenols having alkyl groups of 1-18 carbon atoms, halophenols, alkoxy- and dialkylamino-phenols and dihydroxybenzenes. Specified aromatic amines are aniline, benzene-diamines, alkyl-substituted anilines and benzenediamines having alkyl groups of 1-4 carbon atoms and N-alkylaminoanilines. Specified aldehydes are formaldehyde, acetaldehyde, propionaldehyde and chloral. The molar proportion of phenol to aromatic amine may range from 15: 1 to 1: 15, and the molar proportion of phenol and aromatic amine to aldehyde may range from 6: 1 to 1.2: 1. Specified epoxides for use in the addition reaction are alkylene oxides of 2-10 carbon atoms and their halogen substitution products, aryl glycidyl ethers, aryl-substituted alkylene oxides and cycloalkylene oxides. The proportion of epoxide reacted may range from 0.25 to 30 mols. per equivalent of reactive hydrogen atoms in the condensation product. Up to 1 mol. of epoxide per equivalent of phenolic hydroxy groups in the condensation product may be caused to react without the use of a catalyst, but the addition of further epoxide groups requires the use of a catalyst, e.g. an alkali or alkaline-earth metal hydroxide or alkoxide, a tertiary aliphatic amine, a quaternary ammonium or phosphonium hydroxide or alkoxide, a proton acid or a Lewis acid. The addition reaction may be effected at 100-220 DEG C. and atmospheric, reduced or raised pressure. The products may be used (1) as hardeners for polyepoxide resins, (2) in the manufacture of reaction products with polyethers such as polyoxyethylene, (3) as surfactants, ion-exchange resins and chelating agents and (4) in the manufacture of esters, useful as surface coatings, with drying-oil acids. Examples are given of the manufacture of condensation products from several phenols and aromatic amines and formaldehyde, and of the reaction of these products with propylene oxide. A further example is given also in which a phenol-aniline-formaldehyde condensation product is treated with ethylene oxide in the absence of a catalyst, and the product is then further treated with propylene oxide in the presence of potassium hydroxide as a catalyst.