Patent GB-738647-A (GB)
Title: Manufacture and use of new condensation products from aldehydes and nitrogenous bases and their use for improving the properties of dyeings
IPC: C08G12/10
Filed: 1951-08-03
Abstract: Condensation products of a salt of a polyamine with an inorganic acid, a non-cyclic compound containing the grouping <FORM:0738647/IV (c)/1> and an aldehyde (see Group IV (a)) are used in aqueous solution, if desired as their salts, for improving the wet fastness of dyeings or prints from water-soluble direct-dyeing dyestuffs containing sulphonic or carboxylic acid groups, or for rendering fabrics crease-resistant.  After-treatment preferably takes place at 70-75 DEG  C. and the bath may contain soluble copper salts, e.g. the sulphate, formate or acetate, or complex copper compounds, or the copper compounds may be applied in a separate bath following the treatment with the condensation product.  The copper treatment is particularly desirable with dyes containing at least once the grouping <FORM:0738647/IV (c)/2> in which X=OH or COOH and the pair of carbon atoms to which X is bound belong to the residue of a cyclic diazo component while the other pair belong to the residue of a coupling component.  In examples: (10) and (11) cotton fabric dyed with a dyestuff from diazotized dehydrothiotoluidine disulphonic acid and acetoacetic acid orthoanisidide or from diazotized 4-amino-azobenzene-41-sulphonic acid and 2-(31 - acetylamino) - benzoylamino - 5 - oxynaphthalene - 7 - sulphonic acid is treated with an aqueous solution of a condensation product of diethylene triamine hydrochloride, dicyandiamide and formaldehyde.  The wet fastness of the dyeings is improved.  In example (12) dyed regenerated cellulose staple fibre fabric is treated with an aqueous solution of methylol urea, ammonium chloride, copper acetate and the condensation product from diethylene triamine hydrochloride, dicyandiamide and formaldehyde.  The fabric is rinsed and dried and is crease-resistant, the dyeing is fast to washing.  A number of other similar examples are given.  Specification 467,166 is referred to.ALSO:A non-cyclic compound containing at least once the grouping <FORM:0738647/IV (a)/1> is condensed with an aldehyde and a water-soluble salt of an inorganic acid and an aliphatic polyamine containing at least two primary or secondary amino groups at a temperature above 100 DEG  C. The product so obtained may be further condensed with aldehyde. Non-cyclic compounds mentioned are dicyandiamide, dicyandiamidine, guanidine, acetoguanidine, biguanide, alkyl- or aryl-biguanides.  Aldehydes mentioned are formaldehyde, acetaldehyde and acrolein.  Preferably paraformaldehyde is used in the main reaction and formalin in the second aldehyde condensation (if any).  Amines mentioned are alkylene diamines, their N-alkyl or N-oxyalkyl substitution products, polyalkylene polyamines or products obtained by reacting ethylene dihalide or glycerol dichlorhydrin with ammonia or an amine, e.g. monoethanolamine. The salts may be chlorides or sulphates and all the amino groups are neutralized by the acid.  The initial reaction may be performed in an inert solvent, e.g. butanol, amyl alcohol, 2-ethyl butanol, or 2-ethyl hexanol, if desired in a closed vessel.  If desired the non-cyclic nitrogen compound is first reacted with the amine salt (ammonia usually being evolved) and the product then reacted with the aldehyde.  This procedure is especially favourable with dicyandiamide and ethylene diamine hydrochloride, the reaction with the aldehyde being carried out, if desired, in presence of a solvent or diluent, e.g. glacial acetic acid or tetrahydrofurfuryl alcohol.  The second condensation with aldehyde may be carried out at a temperature above 70 DEG  C., e.g. 90-100 DEG  C., in the presence of acids, e.g. HCl, H2SO4, formic or acetic acid, or of alkali, e.g. alkali hydroxides or alkali carbonates, and if desired, under pressure.  The products, if desired as salts, are used in aqueous solution, e.g. with addition of a water-soluble copper compound in dyeing or for crease-resisting textiles (see Group IV (c)).  In example (1) diethylene triamine hydrochloride, dicyandiamide and paraformaldehyde are condensed by boiling in n-butanol, the solid product then condensed with aqueous formaldehyde, the pH adjusted to 9 and the product dried.  Example (2) is similar, the final product giving a water-soluble acetate. (3) Ethylene diamine hydrochloride and dicyandiamide are heated together and then reacted with paraformaldehyde.  The product is reacted with aqueous formaldehyde and the pH adjusted to 9.  Several similar examples are given and a number of examples relating to the use of the products for treating textiles is also given. Specification 467,166 is referred to.