Patent GB-489429-A (GB)
Title: Improvements in producing fast dyeings
IPC: C09B39/00
Filed: 1936-12-24
Abstract: Cellulosic material and regenerated cellulose or mixtures containing them are dyed by treating the goods with a solution of a diazo compound having affinity to the goods to be dyed as defined below, and with a coupling component.  The diazo compound must have at least one of the following characteristics: a group consisting of 3 or more nuclei which consists of aromatic or heterocyclic rings having from 5 to 6 members, the said rings being connected so that the molecule contains a continuous chain of conjugated double bonds: the grouping-NHCONH-; two or more carboylamino groups or two or more <FORM:0489429/IV/1> groups (as in cyanuric ring compounds); a group R-N = N-R1, R-CH = CH-R1 or R-N = CH-R1, wherein R and R1 are aromatic radicles.  Furthermore, they must contain at least one aza nitrogen atom in a 6-membered ring or a quaternary nitrogen atom, or a polyglycol ether radicle. Diazonium double salts, anti-diazotates, nitrosamines, diazosulphonic acids, diazo anhydrides and diazoamino compounds may be used and may be applied simultaneously with the coupling component.  Agents promoting coupling may also be used. Multicolour designs may be produced by allowing two or more coupling components to act at different times and places and such components may be applied in a printing process.  The dyeings may be after-treated in any desired manner.  In examples: (1) cotton is treated with a solution of diazotized 3-amino-7 : 8-benzacridine or 2-methyl-3-amino-7 : 8-benzacridine and introduced into a solution of 1-phenyl-3-methyl-5-pyrazolone (yellow), using diazotized aminobenzphenazine (formula given) an orange-yellow is obtained; in a similar manner the following dyes are made on cotton; (2) diaminodiquinolinonaphthalene \sQ 1-(41-sulphophenyl)-3-carboxy-5-pyrazolone (yellow); 2 : 6-diamino-9 : 10-dichlorodiphendioxazine--> b -naphthol (violet); (3) 2 - N - methyl - N - o  - hydroxyethoxyethoxyethoxyethyl - 4 - aminoanthrapyrimidine (from 2 - bromo - 4 - aminoanthrapyrimidine and methylaminoethyltriglycol) --> b -naphthol (red); (4) 1-aza-2-(41-aminophenyl)-phenanthrene (from b -naphisatin and p-aminoacetophenone and splitting off the COOH group) --> b -naphthol (red) or 1-phenyl-3-methyl-5-pyrazolone (orange yellow); 1-aza-2-(41-aminophenyl-4-carboxy-9-chloranthracene (from 1-chlor-2(N)-3-naphthisatin and p-aminoacetophenone) and its methyl ester, 1-aza-2-(41-aminophenyl) - 9 - chloranthracene (obtained by decarboxylating the above 4-carboxy compound), 2 - (41-aminophenyl) - quinoline and its 4 - carboxymethyl ester, 9 - (41 - aminophenyl)-phenanthridine, 4 : 41 - diaminodiazaterphenyl (from 4 - amino - o  - chloracetophenone and ammonia), 3 : 41-diamino-9-phenylacridine and 2 : 7 - dimethyl - 9 - (41 - aminophenyl) - acridine may be also used as diazo component; (5) 9 : 10 - (41 - aminophenyltriazolo) - 4 - azaphenanthrene (by oxidizing p-nitroaniline --> 9-aminoazaphenanthrene and reducing) --> 2-chloracetyl J-acid (red on viscose artificial silk), b -naphthol, 1- or 2-ethylaminonaphthalene, m-phenylene diamine, 1 : 3 - diamino - 4 - chlorobenzene, resorcinol, 1-methyl-2 : 4-diaminobenzene, phenol, 2-aminonaphthalene-5- or 6-sulphonic acid, N-benzoyl K-acid, 1-phenylaminonaphthalene - 8 - sulphonic acid, g  - acid, the anilide or b -naphthylamide of 2 : 3-oxynaphthoic acid or diacetoacetyltolidine; other diazo components specified are 7 : 8-(41-aminophenyltriazolo)-4-azaphenanthrene (by oxidizing p-nitroaniline --> 7-amino-4-azaphenanthrene and reducing the nitro group), 5 : 6-(41-aminophenyltriazolo) - quinoline (by oxidizing p-nitroaniline --> 6-aminoquinoline and reducing), and 9 : 10 - (41 - aminophenylthiazolo) - 4-azaphenanthrene (by converting 10-amino-4-azaphenanthrene into 10-amino-9-mercapto-4-azaphenanthrene and then into the 9 : 10-(41-nitrophenylthiazolo) - 4 - azaphenanthrene and reducing; (6) the quaternary salt from 9 : 10-(41 - aminophenyltriazolo) - 4 - azaphenanthrene and dimethyl sulphate --> 2-chloracetyl J-acid or 2-isobutylaminonaphthalene-7-sulphonic acid (red); (7) 5 : 51-diamino-8 : 81-diquinonyl urea (from 8-aminoquinoline and phosgene, nitration and reduction \sQ b -naphthol (violet on regenerated cellulose); other diazo components specified are 6 - aminobenzoylaminobenzoylaminoquinoline (from 6-aminoquinoline and p-nitrobenzoylchloride), 411 - aminobenzoyl - 41-aminophenyl - 6 - carboylaminoquinoline (by condensing quinoline-6-carboxylic acid chloride with p-nitroaniline, reducing, condensing with p-nitrobenzoyl chloride and again reducing) and 9 - (41 - aminobenzoylamino) - 4 - azaphenanthrene (from 9-amino-4-azaphenanthrene and p-nitrobenzoyl chloride); (8) the reduced condensation product from cyanuric chloride (1 mol.), 8-aminoquinoline (2 mols.) and p-nitroaniline (1 mol.), the reduced condensation product from cyanuric chloride (1 mol.), p - nitroaniline (2 mols.) and 8-aminoquinoline (1 mol.) and the condensation product from 2-(41-nitrophenyl)-4 : 6 - dichloro - 1 : 3 : 5 - triazine (1 mol.) and 8-aminoquinoline (2 mols.) may be used as diazo component in the foregoing examples; (9) cotton is treated with diazotized 6-aminoquinoline --> aminohydroquinone dimethyl ether and developed with b -ethylnaphthylamine; a -4-aminophenyl-b -6-quinolyl-ethylene (from quinoline-6-aldehyde and p-nitrophenylacetic acid and reduction) is also specified; (10) a mixed fabric of cellulose hydrate and wool is treated in a solution of the benzene sulphonate of diazotized 9 : 10-(41-aminophenyltriazolo)-4-azaphenanthrene and introduced into a bath containing the sodium salt of 2-isobutylaminonaphthalene-7-sulphonic acid and anthosine BN (level red).  Aminopyridinopyrenes are also specified as diazo components.