Patent GB-110066-A (GB)
Title: Manufacture of New Azo-dyestuffs and Metal Compounds thereof and Application of the said Dyestuffs and Compounds in Dyeing.
Inventor: IMRAY OLIVER
IPC: C09B45/14
Filed: 1916-12-19
Abstract: 110,066. Imray, O., (Soc. of Chemical Industry in Basle). Dec. 19, 1916. Azo dyes are obtained by coupling diazo compounds of the benzene or naphthalene series with the condensation products (coumarin derivatives) from phenols or naphthols and acetoacetic or oxaiacetic ester, or the coumaric acids obtained by treating these coumarin derivatives by caustic alkali. The products obtained by the use of ooxydiazo compounds, diazocarboxylic acids, or diazosalicylic acids, are mordant wool dyes and may be dyed with chromium, copper, &c. mordants by the usual methods; they may also be converted into water-soluble metal (copper, chromium, aluminium, iron, nickel, cobalt, zinc, uranium, vanadium, cerium, &c.) compounds by the methods described in Specifications 26460/12, 1611/15, 12:349/15, 16803/15, and 16916/15. The copper compounds may also be made by the process described in Specification 15127/15; the chromium compounds may also be made by the process described in Specification 15456/15. The metal compounds dye wool in acid baths; the dyeings may, when the parent dyes are derived from diazocarboxylic acids or diazosalicylic acids, be subsequently chromed as described in Specification 13204/15. Examples of the production of the dyes and of their copper, chromium, and iron compounds are given. A table is given of the shades produced by the dyes, and copper and chromium compounds thereof, from the following pairs of components : - 7 - oxy - 4 - methyl - 1 : 2 - benzpyrone (the condensation product from resorcin and acetoacetic ester) and diazotized 2 - aminophenol - 4 - sulphonic acid, 4 - sulpho - 2 - aminophenol - 6 - carboxylic acid, 4-methyl - 2 - aminophenol - 6 - sulphonic acid, 4-acetamino - 2 - aminophenol - 6 - sulphonic acid, picramic acid, 4 - chlor - 2 - aminophenol - 6 - sulphonic acid, 1 : 2: 4-aminonaphthol sulphonic acid, 4- chlor - 2 - aminophenol, 4 - nitro - 2 - aminophenol, 6 - nitro - 4 - methyl - 2 - aminophenol, m-aminobenzoic acid, 4 - aminophenol - 2 - carboxylic acid, 4 - nitro - 2 - aminophenol - 6 - carboxylic acid, 6- nitro - 2 - aminophenol - 4 - sulphonic acid, or 4 - chlor - 2 - aminophenol - 6 - carboxylic acid: 7 - oxy - 4 - carboxy - 1 : 2 - benzpyrone (the condensation product from resorcin and oxalacetic ester) and diazotized 2 - aminophenol - 4 - sulphonic acid, 4 - sulpho - 2 - aminophenol - 6 - carboxylic acid, 4 - methyl - 2 - aminophenol - 6 - sulphonic acid, 4 - acetamino - 2 - aminophenol - 6 - sulphonic acid, picramic acid, 4 - chlor - 2 - aminophenol - 6-sulphonic acid, or 1 : 2 : 4-aminonaphthol sulphonic acid; the condensation product from 1: 6- dioxynaphthalene and acetoacetic ester, and diazotized 2 - aminophenol - 4 - sulphonic acid, 4- sulpho - 2 - aminophenol - 6 - carboxylic acid, or 4 - chlor - 2 - aminophenol - 6 - carboxylic acid; the condensation product from 2 : 7 - dioxynaphthalene and acetoacetic ester. and diazotized 2 - aminophenol - 4 - sulphonic acid, 4 - sulpho - 2 - aminophenol - 6 - carboxylic acid, or 4 - chlor - 2 - aminophenol-6-carboxylic acid; the condensation product from p-cresol and acetoacetic ester, and diazotized 6 - nitro - 2 - aminophenol - 4 - sulphonic acid; the condensation product from alpha -naphthol and acetoacetic ester, and diazotized 4 - chlor - 2 - aminophenol-6-carboxylic acid. A table is also given of the shades obtained by aftertreating with the following metallic salts the dyeings of the dye from diazotized 4 - chlor - 2 - aminophenol - 6 - sulphonic acid and 7 - oxy - 4 - methyl - 1 : 2 - benzpyrone :-sodium bichromate, copper sulphate, cobalt nitrate, nickel sulphate, ferrous sulphate, zinc sulphate, aluminium sulphate, ammonium uranate, ammonium vanadate, and cerium acetate. Coumarin derivatives; coumaric acids.-The condensation of phenols or naphthols (e.g. resorcin, p-cresol, hydroquinone, or a naphthol) with acetoacetic or oxalacetic ester to produce coumarin derivatives is known; the condensation products from dioxynaphthalenes are obtained similarly; examples are given of the condensation of 2 : 7 - or 1: 6 - dioxynaphthalene with acetoacetic ester; the products may be sulphonated. The coumarin derivatives on heating with caustic soda lye give the sodium salts of the corresponding coumaric acids. o-Aminophenol derivatives. - The following nitro bodies : 5 - nitro - 2 - aminophenol - 4 - sulphonic acid, 5 - nitro - 6 - methyl - 2 - aminophenol - 4 - sulphonic acid, 5 - nitro - 4 - chlor - 2 - aminophenol - 6 - sulphonic acid, 5 nitro - 6 - chlor - 2 - aminophenol - 4 - sulphonic acid, 5 - nitro - 4 - chlor - 2 - aminophenol - 6 - carboxylic acid, are obtained by nitrating the acidyl or urca derivatives of the parent aminophenols and saponifying the products. o-Aminophenol derivatives are also obtained by partial reduction of 2 : 4 : 6 - trinitro - m-cresol, 2 : 4 : 6 - trinitro -m-chlorphenol, 2 : 4: 6 - trinitrophenol - m-sulphonic acid, 2 : 4: 6- trinitrophenol - m-carboxylic acid, or 2 : 3 : 4 : 6- tetranitrophenol. These o-aminophenol derivatives may be used as parent materials in the production of the dyes described above.