Patent GB-523547-A (GB)
Title: Production of new azo dyestuffs on cellulose materials and of intermediates therefor
IPC: C09B29/20
Filed: 1939-01-03
Abstract: 523,547. Dyeing textiles ; arylamides of 2:3- hydroxynaphthoic acid. MARRIOTT, G. J., SAUNDERS, K. H., and IMPERIAL CHEMICAL INDUSTRIES, Ltd. Jan. 3, 1939, No. 200. [Classes 2 (iii) and 15 (ii)] 41-Benzoylamino- or 4<SP>1</SP>-phenoxyacetylamino- 2<SP>1</SP>-5<SP>1</SP>-di (#-hydroxyethoxy)-anilides of 2:3- hydroxynaphthoic acid, in which the nuclei of the benzoyl or phenoxyacetyl residues may be substituted, e.g., by alkoxy or halogen, are obtained by condensing the 4-amino-2:5-di- (#-acetoxyethoxy)-anilide of the benzoic or phenoxyacetic acid (obtained by reaction of 2:5- di-(#-acetoxyethoxy)-aniline (cf. Specification 422,417), with the corresponding acid halide, nitrating and reducing the nitro group) with 2:3-hydroxynaphthoic acid, or an ester or the chloride thereof, and hydrolyzing. The products may be applied to cellulosic fibre and coupled on the fibre with diazo compounds free from sulphonic, carboxylic or like solubilizing groups to obtain readily dischargeable brownish dyeings. In examples (1) 2:5-di-(#-acetoxyethoxy)-aniline is condensed with benzoyl chloride in benzene in presence of potassium acetate, the condensation product is nitrated and the nitro group reduced and the resulting amine is treated with 2:3-hydroxynaphthoic acid in toluene at 60‹ C. with slow addition of phosphorus trichloride followed by boiling under reflux. pouring into water, making alkaline with sodium carbonate, distilling off the toluene in steam, filtering off the insoluble material, dissolving the precipitate in boiling dilute sodium hydroxide and precipitating the free anilide by addition of acid; (2) cotton yarn is impregnated with an aqueous solution containing the anilide of (1). sodium hydroxide and Turkey red oil neutralized with sodium carbonate, and treated with a solution of diazotized 4-chloro- 2-nitraniline. squeezed, rinsed and treated with a boiling aqueous solution of sodium carbonate and soap to obtain a dull reddish brown dyeing, fast to light; a table is given showing the shades obtainable with the use, as diazo components, of 3-chloraniline, 2:5-dichloraniline, 1-aminoanthraquinone, 5-chloro-2-aminotoluene and 4- and 5-nitro-2-aminoanisoles ; the Provisional Specification refers also to the use of the corresponding o-chlorobenzoyl, p-anisoyl and mbromobenzoyl in place of the benzoyl derivative; (3) 2:5-di-(#-acetoxyethoxy)-aniline is condensed with phenoxyacetyl chloride in benzene in presence of sodium acetate, the condensation product is nitrated and the nitro group reduced, and the product is condensed with 2:3-hydroxynaphthoic acid and hydrolysed ; (4) cotton yarn impregnated with the anilide of (3) is developed with diazotized 4-chloro-2-nitraniline to a dull reddish brown, fast to light ; a table is given showing the shades obtainable with the use of other diazo components, including 2- nitraniline and others referred to in (2) ; (5) 2:5-di-(#-acetoxyethoxy)-aniline is condensed with 4-anisoyl chloride in benzene in presence of potassium acetate, the condensation product is nitrated and the nitro group reduced, and the product is condensed with 2:3-hydroxynaphthoic acid and hydrolysed ; (6) cotton cloth impregnated with the anilide of (5) is printed with an aqueous paste containing the double salt of zinc chloride and anthraquinone-1-diazonium chloride, wheat starch-tragacanth mucilage and acetic acid, dried, immersed in sodium bisulphite solution, rinsed and treated with a boiling aqueous solution containing sodium carbonate and soap to obtain a fast reddish brown print; (7) 2:5-di-(#-acetoxyethoxy)- aniline is condensed with 3-bromobenzoyl chloride in benzene in presence of potassium acetate, the condensation product is nitrated and the nitro group reduced, and the product is condensed with 2:3-hydroxynaphthoic acid and hydrolyzed ; (8) cotton yarn impregnated with the anilide of (7) is developed with diazotized 5-chloro-2-aminoanisole to a bluish red, fast to light ; the shades similarly obtainable with the use, as diazo components, of 4-chloro-2-aminoanisole, 4-chloro-2-nitraniline and 1-aminoanthraquinone are specified. Specification 489,934 also is referred to.