Patent GB-298494-A (GB)
Title: Manufacture and application of dyestuffs containing metal
IPC: C09B43/16
Filed: 1928-10-08
Abstract: 298,494. Soc. of Chemical Industry in Basle. Oct. 8, 1927, [Convention date]. Azo dyes, soluble metal compounds of.-Azo dyestuffs containing metal, with or without other compounds containing a suitable group or groups, are condensed with cyanuric halides. The products may be subjected to further treatment, such as coupling with a diazo compound or diazotization ,and further coupling in substance or on the fibre, reduction, condensation, acidylation (including treatment with phosgene), alkylation, aralkylation, or ablation. The following examples are specified. (1) 1 Mol. of the copper compound of the dyestuff 2-aminophenol-4-sulphonic acid # (alkaline) 2 : 5 : 7-acid is condensed with 1 mol. of cyanuric chloride; the product dyes cotton, wool, and silk bluish red. (2) 1 Mol. of the chromium compound of the dyestuff 1 : 2 - aminonaphthol-4-sulphonic acid # anaphthol is subjected to nitrosation and reduction and condensed with 1 mol. of cyanuric chloride and 1 mol. of aniline; the product dyes cotton, wool, and silk blue-grey. (3) 2 Mols. of the chromium compound of the dyestuff 1 : 2-aminonaphthol-4-sulphonic acid # 3-aminophenol are condensed with 1 mol. of cyanuric chloride; the product, which dyes cotton, wool, and silk greyviolet, may be further condensed with 1 mol. of a compound containing an -OH, -SH or -NH2 group; the product so obtained with 1 mol. of aniline dyes cotton, wool, and silk blue-violet; the corresponding product from 2 mols. of the chromium compound of the dyestuff obtained by reduction of the product from the nitrated diazo compound of 1 : 2-aminonaphthol-4-sulphonic acid and 1-phenyl-3-methyl-5-pyrazolone (cf Specification 295,594), 1 mol. of cyanuric chloride, and 1. mol of aniline gives red dyeings; if the pyrazolone is replaced by 1-oxynaphthalene-8-sulphamide the dyeings are blue-green; if, in addition, the aniline is replaced by 1-chloro-2 : 4- phenylenediamine, the dyeings ma.y be diazotized on the fibre and developed with #-naphthol; the corresponding product from 2 mols. of the copper compound of the dyestuff 2-aminophenol-4-sulphonic acid # (alkaline) 2 : 8 : 6-acid, 1 mol. of cyanuric chloride, and 1 mol. of aniline gives 'blue-red dyeings. (4) 3 Mols. of the chromium compound of the dyestuff obtained by reduction of the product from the nitrated diazo compound of 1: 2-aminonaphthol-4-sulphonic acid and anaphthol are condensed with 1 mol. of cyanuric chloride; the product dyes cotton, wool, and silk grey. (5) The condensation product from 1 mol. of 2 : 5 : 7-acid and 1 mol. of cyanuric chloride is condensed with the product obtained by simultaneous chroming and reduction of the dyestuff 6-nitro-2-aminophenol-4-sulphonic acid # #- naphthol; the product, which dyes cotton, wool, and silk violet, may be further condensed with 1-chlor-2 : 4 - phenylenediamine, whereupon the product may be diazotized and coupled with #- naphthol in substance or on the fibre, the final dyeings being brown-red, or the product may be coupled in substance or on the fibre with diazo compounds, the final dyeings using the diazo compounds of p-nitraniline and of aniline being red-violet and brown-red respectively. (6) 2 Mols. of the copper compound of the dyestuff 2- aminophenol-4-sulphonic acid # (alkaline) 2 : 8 : 6-acid are condensed with 1 mol. of cyanuric chloride and 1 mol. of 1-chloro-2 :4-phenylenediamine; the product, which dyes cotton, wool, and silk bluish red, may be diazotized on the fibre and developed with #-naphthol. (7) 1 Mol. of the dyestuff 2-aminonaphthalene-4 : 8-disulphonic acid # cresidine and 1 mol. of the copper compound of the dyestuff 2-aminophenol- 4-sulphonic acid # (alkaline) 2: 5 :7-acid are condensed with 1 mol. of cyanuric chloride; the product, which dyes cotton, wool, and silk brown, may be further condensed with 1 mol. of aniline. (8) 1 Mol. of the chromium compound of the dyestuff 1 : 2-aminonaphthol-4-sulphonic acid # 1 : 5-aminonaphthol, 1 mol. of the copper compound of the dyestuff 1 : 2-aminonaphthol-4-sulphonic acid # 3-aminophenol, and 1 mol. of aniline are condensed with 1 mol. of cyanuric chloride : the product dyes cotton, wool, and silk violet; if the aniline is replaced by 1-chlor-2 : 4- phenylenediamine., the dyeings, may be diazotized and developed with #-naphthol, resorcinol, or 1- phenyl-3-methyl-5-pyrazolone. (9) 1 Mol. of the chromium compound of the dyestuff 1 : 2-aminonaphthol-4-sulphonic acid # a-naphthol is subjected to nitrosation and reduction and condensed with 1 mol. of cyanuric chloride, 1 mol. of paminoacetanilide, and 1 mol. of aniline, and the condensation product is saponified and treated with phosgene; the disazo product dyes cotton, wool, and silk blue. (10) 1 Mol. of the product obtained by simultaneous chroming and reduction of the dyestuff 6-nitro-2-aminophenol- 4-sulphonic acid # #-naphthol is condensed with 1-mol. of cyanuric chloride, 1 mol. of pphenylenediamine, and 1 mol. of aniline; the product dyes cotton, wool, and silk violet. A table is also given showing the colours of the dyeings obtained on cotton, wool, and silk with the products of condensation of 1 mol. of cyanuric chloride with the following components :-2 mols. of the copper compound of the dyestuff 3- amino-5-sulphosalicylic acid # alpha-naphthylamine; 2-mols. of the same copper compound and 1 mol. of aniline; 2 mols. of the copper compound of the dyestuff 3-amino-5-sulphosalicylic acid # 3-amninophenol; 2 mols. of the same copper compound and 1 mol. of aniline; 2 mols. of the copper compound of the dyestuff 2-aminobenzoic acid # (alkaline) 2 : 5 : 7-acid; 2 mols. of the same copper compound and 1 mol. of p-toluidine; 2 mols. of the chromium compound of the dyestuff 5-aminosalicylic acid # (alkaline) 2:5:7- acid and 1 mol. of ammonia; 2 mols. of the chromium compound of the dyestuff 2-aminobenzoic acid # (alkaline) 2:5: 7-acid and 1 mol. of monomethylamine; 2 mols. of the chromium compound of the dvestuff p-aminobenzeneazosalicylic acid and 1 mol. of aniline; 2 mols. of the cobalt compound of the product of reduction of the dyestuff from the nitrated diazo compound of 1 : 2-aminonaphthol-4-sulphonic acid and #-naphthol, and 1 mol. of 1-chlor-2: 4- phenylenediamine; 2 mols. of the nickel compound of the product of reduction of the dyestuff from the nitrated diazo compound of 1 : 2-aminonaphthol-4-sulphonic acid and alpha-naphthol, and 1 mol. of aniline; 1 mol. of the chromium compound of the dyestuff 4-nitro-2-aminophenol # (alkaline) 1:2- aminonaphthol - 3 : 6-disulphonic acid, 1 mol. of p-aminobenzeneazosalicylic acid, and 1 mol. of aniline ; 1 mol. of the dyestuff 2- aminonaphthalene - 4 : 8 - disulphonic acid # cresidine, 1 mol. of the chromium compound of the product of reduction of the dyestuff from the nitrated diazo compound of 1 : 2-aminonaphthol- 4-sulphonic acid and 5 : 8-dichlor-1-naphthol, and 1 mol. of aniline; 1 mol. of the chromium compound of the product of saponification of the dyestuff 4-acetylamino - 2 - aminophenol-6-sulphonic acid # pyrogallol, and 2 mols. of aniline. Specification 209,723 also is referred to. The Specification as open to inspection under Sect. 91 (3) (a) comprises also a reference to a dyestuff obtained by condensation of 1 mol. of cyanuric chloride with 1 mol. of the chromium salt of p-aminosalicylic acid and 1 mol. of the dyestuff p-aminobenzeneazosalicylic acid. This subject matter does not appear in the Specification as accepted.