Patent GB-812151-A (GB)
Title: Improvements relating to metal-containing tricyclic chelating monoazo dyestuffs and their use
IPC: C09B45/14
Filed: 1955-10-06
Abstract: The invention comprises metal compounds which contain one atom of chromium or cobalt in complex union with one molecule of a dyestuff of formula X1-A-N = N-B-X2 where A is a benzene residue with X1 oto the azo group, B is a naphthalene or pyrazolone residue with X2 in a neighbouring position to the azo group, one X is a metallizable group and the other is the residue -(SO2)n-NH-D where D is an organic residue containing a group taking part in the complex formation and n is 0 or 1 and with one molecule of a coordinative divalent complex former.  The complexes are readily water-soluble and the dyestuffs occupy 4 co-ordination positions at the complex metal atom whilst forming three 5- or 6-membered chelate rings.  The dyestuffs are made by treating a dyestuff of the above formula with an agent yielding chromium or cobalt in the presence of a co-ordinative divalent complex former, by reacting a 1,1-metal complex of a dyestuff of the above formula with the divalent complex former or by reacting the dyestuff with a metal complex of a divalent complex former. Specified values for one X are OH, COOH and alkoxy and the other X may be b -aminopropionic acid, o-carboxy and -hydroxy-phenyl-amino, quinolinyl-8-amino, sulphonic acid glycinide, sulphonic acid amide-b -propionic acid and sulphonic acid-o-carboxy-and -hydroxy phenylamide radicles. Indicated as diazo components are 2-aminobenzenesulphonic acid amides which contain a propionic, o-carboxy or -hydroxy-phenyl residue as substituents at the N atom of the amide group and 2-amino-phenols, -alkoxyphenols and -1-carboxylic acids. Coupling components mentioned are 5-pyrazolones, naphthols, 2-naphthyl - b  - aminopropionic acid and 2-(o-carboxy- and -hydroxy - phenylamino) - naphthalenes.  Divalent complex formers mentioned are a -hydroxy- and -amino-carboxylic acids, vicinol dihydroxyaryls, o - amino - hydroxyaryls, 8-hydroxy-quinolines or benzoquinolines, o-hydroxy-aldehydes and -ketones, o-hydroxy-azo and -benzene - azo - methenes, 1,2 - diaminoalkanes, pyridine, benzopyridine - 2 - carboxylic acids and o-nitrosonaphthols and they may contain halogen, sulphonic acid and sulphonamide substituents.  The dyestuffs dye polypeptide fibres such as wool and superpolyamides and -urethanes. In examples and a table which illustrate the preparation of the dyestuffs and their use in dyeing wool in yellow or green shades, the diazo components are 2-aniline - 1 - sulphonic acid glycinide and 21-carboxyphenylamide, 5-nitro-2-aminophenol- and 2 - aminophenol - 4 - methyl and -ethylsulphones, 3 - amino - 4 - hydroxy - 31 - sulphonamido - diphenyl sulphone, 5 - nitro - 4 - chloro- and 5 - nitro - 2 - aminophenol, 5 - nitro - 2 - and 5 - nitro - 2 - aminophenols, 5 - nitro - 2 - aminobenzoic acid and 2-aminobenzoic acid, the coupling components being 1-(31-chlorophenyl)- and 1 - phenyl - 3 - methyl - 5 - pyrazolones, 2 - (21 - carboxyphenyl)-, -(51 - chloro - 21-carboxyphenyl)-and -b -carboxyethyl - naphthylamines, 2-naphthol and 7-methoxy-2-naphthol and the complex formers are 8-hydroxy- and 5 - chloro - 8 - hydroxy - quino - lines, picolinic, quinaldic and salicylic acids, salicylaldehyde, o - hydroxyacetophenone, the reaction products of salicylaldehyde with aniline and methyl and butylamines, 5-hydroxy-aza-(4)-phenanthrene and ammonium chromosalicylate. Specification 560,787, [Group IV], is referred to.  Reference has been directed by the Comptroller to Specifications 778,262 and 790,904.