Patent GB-423864-A (GB)
Title: The manufacture of new nitrogenous condensation products
IPC: C07D251/70
Filed: 1933-08-02
Abstract: A mixture of polyethylenepolyamines of the formula H2N(C2H4NH)nC2H4NH 2 (obtainable from dihalogenethanes and aqueous ammonia) is condensed (a) with a compound containing at least two acylating groups, or (b) with a compound containing at least one acylating and one alkylating group, the proportions of the reagents being such that basic products are obtained.  Suitable reagents of type (a) are cyanuric halides such as cyanuric chloride, cyanuric acid dichloride, and 1-methylamino (or 1-amino)-3 : 5-dichlorotriazine, and also cyanuric acid, oxalic acid, oxalyl chloride, maleic anhydride, fumaric esters, terephthaloyl chloride, and benzene or naphthalene disulphochlorides. Suitable reagents of type (b) are compounds containing a halogenalkyl, sulphoalkyl or arylsulphonic ester group, and also a carboxylic acid or ester group or a carboxylic or sulphonic acid halide group; specified reagents of type (b) are chloracetyl chloride, chlorethanesulphochloride, chloromethylbenzenesulphochlorides, and dihalogenadipic acids and their homologues.  A modification of the process consists in condensing the polyamine mixture with a compound containing at least two organic acid amide groups or one organic acid amide group and another acylating or an alkylating group; in this modification, the polyamine mixture may react with the amide groups with liberation of ammonia.  Specified reagents for use in this modification are oxamide; nitrogenous derivatives of carbonic acid such as urea and its alkyl and aryl derivatives, biuret, semicarbazide, guanylurea, allantoin and pyruvil; uric acid and its esters; ureides; allophanic acid chloride; biuretcarbonic acid chloride; and chloracetamide.  The products and their salts are generally soluble in water, but may be after-treated with an alkylene oxide, to improve their solubility. Most of the products form lakes with soluble dyes, and can be used for after-treating cellulosic materials dyed with substantive dyes, to improve the fastness of the dyeings.  In the examples: (1) a polyethylenepolyamine mixture is treated with cyanuric chloride in trichlorethylene solution, or with an aqueous suspension of cyanuric chloride, to yield a product containing chlorine; if the reaction is effected in the presence of soda solution, a product free from chlorine is obtained; similar products are obtained if cyanuric acid dichloride or cyanuric acid amide dichloride is used in place of cyanuric chloride; details are given of the treatment of the first product of the example with ethylene oxide, instead of which propylene oxide, butylene oxide or glycide may also be used; (2) a polyethylenepolyamine mixture is treated with cyanuric chloride in trichlorethylene or chloroform solution to yield a product of unspecified constitution; a similar product is obtained by treating the polyamine mixture with a condensation product from one mol. of cyanuric chloride and two mols. of monoethanolamine; (3) a polyethylenepolyamine mixture is treated with oxalyl chloride in trichlorethylene solution to yield a product of unspecified constitution; (4) a polyethylenepolyamine mixture is heated with biuret, which may be taken as a crude product obtained by treating fused urea with chlorine; a product of unspecified constitution is obtained, with evolution of ammonia.  Samples have been furnished under Sect. 2 (5) of products obtained from a polyethylenepolyamine mixture and (1) terephthaloyl chloride; (2) naphthalene - 2 : 7 - disulphochloride ; (3) chloracetyl chloride; (4) p-chloromethylbenzenesulphochloride; (5) hydantoic acid ethyl ester; (6) allophanic acid chloride.