Patent GB-543092-A (GB)
Title: New nitrogen compounds, process for their preparation and their industrial application
IPC: C07G99/00
Filed: 1940-07-06
Abstract: 543,092. Resinous condensation products ; organic nitrogen compounds ; dyeing. textiles tanning. COMPAGNIE NATIONAL DE MATIERES COLORANTES ET MANUFACTURES<SP> </SP>DE<SP> </SP>PRODUITS CHIMIQUES DU NORD REUNIES ETABLISSEMENTS KUHLMANN. July 6, 1940. No. 11326. Convention date, July 8, 1939. [Class 2 (iii) and 15 (ii),] [Also in Group VIII] Nitrogen compounds are prepared by heating together urea and an alkylolamine, and treating the product at ordinary or elevated temperatures with an ester of an inorganic acid. Alternatively, the alkylolamine may be treated with the ester at ordinary or elevated temperature, and the product heated with urea. The product of either of these processes may be treated with an aldehyde, or compounds which give rise to aldehydes, such as trioxymethylene, at ordinary or elevated temperature. Modifications comprise (a) heating the urea with the alkylolamine, heating the product with the aldehyde, and then treating the product with the ester at normal or elevated temperature and (b) heating together the urea, alkylolamine and aldehyde, and treating the product with the ester at ordinary or elevated temperature. Specified alkylolamines are mono-, di-, and tri-ethanolamine, N - #-hydroxyethyldiethylamine, N- methyl-diethanolamine, di - #-hydroxyethylaniline, #-γ-dihydroxypropylethylaniline, tri-γ-hydroxypropylamine, and N-#-γ- dihydroxypropyl - diethanolamine. Specified inorganic esters are methyl sulphate, ethyl chloride, amyl chloride, dodecyl chloride, benzyl chloride, and ethylene chloride or bromide. The nitrogen compounds produced are fairly soluble in water and may be used as glues, for the agglomeration in the cold and under pressure of pulverulent substances such as active carbons or building materials of crushed stone and the like, and in the paper, leather, textile or dyestuff industries, e.g. for improving the fastness to water of direct dyes, for increasing the affinity of cellulosic fibres for acid dyestuffs, for the fixation in paper pulp of dyestuffs containing acid groups by formation of insoluble salts of these dyestuffs, and for the precipitation or fixation in leather of natural or synthetic tannins by formation of an insoluble salt between the tannin and the condensation product. In examples, (1) triethanolamine is heated with urea, ethyl alcohol is added followed by methyl sulphate, and the alcohol is distilled off. When a cotton fabric dyed by a direct dyestuff is treated with an aqueous solution of the product, the dyeing becomes fast to water; (2) the product of example (1) is heated with formaldehyde ; (3) triethanolamine is mixed with methyl sulphate, urea is added and the mixture heated ; (4) triethanolamine is heated with urea, trioxymethylene is added and the product heated with benzaldehyde; (5) triethanolamine is heated with urea and the product treated with amyl chloride under heat and pressure. An aqueous solution of the product, which may be treated with formaldehyde, precipitates substantive dyestuffs; (6) triethanolamine is heated with urea and the product heated with ethylene bromide; (7) triethanolamine is heated with ethylene chloride and the product is heated with urea followed or not by treatment in the cold with formaldehyde. Aqueous solutions of the products improve the fastness of direct dyestuffs ; (8) diethanolamine is heated with urea and methyl sulphate added ; the product is dissolved in water, neutralized, if necessary with sodium carbonate, and heated with formaldehyde ; (9) di-#-hydroxyethyl aniline is heated with urea and methyl sulphate added. The product precipitates substantive dyestuffs from aqueous solutions; (10) N-#- hydroxyethyldiethylamine is heated with urea and methyl sulphate added ; (11) #-γ-dihydroxy-propyl-ethylaniline is heated with urea and ethyl alcohol is added, followed by methyl sulphate ; the alcohol is distilled off, and the product heated with formaldehyde ; (12) monoethanolamine is heated with urea and methyl sulphate or a mixture of methyl sulphate and benzyl chloride added; (13) triethanolamine is heated with urea and trioxymethylene, and benzyl chloride added. An aqueous solution of the product increases the fastness of direct dyestuffs on cotton ; (14) and (15) triethanolamine is treated. with methyl sulphate, the product is heated with urea and crotonaldehyde or furfural added. Aqueous solutions of the products fix direct dyestuffs on cotton fibre ; (16) a cotton fabric is impregnated with a solution of the product described in example (2), and dried. The treated fabric fixes acid dyestuffs in neutral or weak acetic acid baths; (17) hides which have undergone a preliminary treatment with vegetable tannins are treated with an aqueous solution of the product of example (2) and, after drying, are treated with a dilute solution of synthetic tannin.