Patent GB-326791-A (GB)
Title: Process for the manufacture of dis- and polyazo dyestuffs
IPC: C09B43/16
Filed: 1928-11-17
Abstract: 326,791. Carpmael, A., (I. G. Farbenindustrie Akt.-Ges.). Nov. 17, 1928. Azo dyes.-Disazo dyes of the type A # M # X and trisazo dyes of the type A # M # M<1> # X in which A represents 1 : 8-aminonaphthol or a derivative thereof, M and M<1> represent the same or different middle components of the benzene or naphthalene series, and X represents a 1-(N-acyl)amino-8-naphthol or a derivative thereof or a 1-(N-heterocyclic)amino-8-naphthol or a derivative thereof, are obtained by effecting the final coupling in presence of pyridine or a derivative thereof. The products give fast blue, bluish-green, grey, and green shades on vegetable fibres and in some cases are suitable for dyeing viscose in even shades. When the acyl or heterocyclic residue of the end component contains a diazotizable amino group the product may be diazotized and coupled with components in substance or on the fibre or may be treated with acid chlorides or anhydrides, such as phosgene, thiophosgene, acetic anhydride, benzoyl chloride, or a nitrobenzoyl chloride or with heterocyclic ccmpounds containing labile halogen atoms, such as chloroquinazolines, chlorophthalazines, 2- halogenbenzothiazoles, or cyanuryl chloride. The following examples are specified :-(1) The dyestuff H-acid # cresidine # 1-(4'-methoxybenzoyl)amino-8-naphthol-6-sulphonic acid gives blue dyeing fast to light on cotton and dark blue dyeings of good fastness and evenness on knitted viscose; the dyestuff 1 : 8-aminonaphthol # cresidine # acetyl-H-acid is a fast bluish-grey; 1 : 8 : 4 : 6 and 1: 8 : 4 : 7-aminonaphtholdisulphonic acids may also be used as first components, aminohydroquinonedimethylether, m - toluidine, and a-naphthylamine as second components, and the following as end components, 1-benzoylamino- 8-naphthol-4-sulphonic acid, the condensation product from 4-chloroquinazoline and 1 : 8 : 4-aminonaphtholsulphonic acid (cf. Specification 310,076) (which yields greenish-blue dyestuffs), the condensation products from 1 mol. of 2 : 4-dichloroquinazoline or a similar heterocyclic compound with two labile halogen atoms, 2 mol. of H-acid, and 1 mol. of aniline or other aromatic amine( cf Specification 309,102), condensation products containing at least one 1 : 8-aminonaphtholsulphonic acid residue attached through the nitrogen atom to the 1 : 3 : 5-triazine ring (of Specification 209,723); these condensation products may be further substituted, e.g. by the residue of 4-amino-4<1>-oxyazobenzene-3<1>-carboxylic acid or of dehydrothiotoluidinesulphonic acid. (2) The dyestuff H-acid # cresidine # 1-(4'-aminobenzoyl)-amino-8-naphthol-6-sulphonic acid gives on cotton powerful blue dyeings which become clear full green, readily dischargeable and fast to washing, light, and over-dyeing, on diazotization on the fibre and development with 1-phenyl-3- methyl-5-pyrazolone; the dyestuff H-acid # cresidine # 1 : 6 - aminonaphthalenesulphonic acid # 1-(3<1>-amino-4<1>-methoxybenzoyl)amino-8- naphthol-6-sulphonic acid gives on cotton blue dyeings which become green and fast to light and washing on diazotization on the fibre and development with 1-phenyl-3-methyl-5-pyrazolone; if the end component of the trisazo product is replaced by a reduced condensation product from Bz-nitrochloro-quinazoline and a 1: 8-aminonaphtholsulphonic acid, the resulting dyestuff is faster to over-dyeing; according to the Provisional Specification the reduced condensation product from 1 mol. of cyanuryl chloride, 1 mol. of 1 : 8 : 6-acid, and 1 mol. of 3-nitraniline is also specified as end component. (3) The dyestuff H-acid # cresidine # 1- (4<1>-acetylaminobenzoyl)amino-8- naphthol-6-sulphonic acid gives on cotton fast blue dyeings; the end component may be replaced by 3<1>-acetylaminophenyl-1 : 2-naphthimidazole-8-oxy- 3 : 6-disulphonic acid or by 1-(3<1>-aminobenzoyl)- amino-8-naphthol-6-sulphonic acid; in the latter case the product may be treated with phosgene to obtain a dyestuff giving fast blue dyeings on cotton; the dyestuff H-acid # cresidine # the condensation product from 1-(41-aminobenzoyl)amino - 8-naphthol-4 : 6-disulphonic acid and 4-chlorquinazoline is simiar. (4) The dyestuff H-acid # cresidine # the condensation product from 1 mol. of terephthaloyl chloride and 2 mols. of 1 : 8 : 6-acid # cresidine # H-acid gives bluish-green dyeings, fast to light, on cotton; the above condensation product may be replaced by condensation products from two or three similar or dissimilar 1 : 8-aminonaphtholsulphonic acids and heterocyclic compounds containing two or three successively replaceable halogen atoms such as 2 : 4-dichloroquinazoline, 1: 4-dichlorophthalazine, cyanuryl chloride, or 2 : 4 : 6-trichloropyrimidine, and 2 or 3 mols. of diazotized aminoazo compounds, at least one of which is of the type 1 : 8-aminonaphtholsulphonic acid # middle component, may be coupled with such condensation products; the 1: 8-aminonaphtholsulphonic acids, except one, in the condensation product forming the coupling component may be replaced by other radicles connected to the heterocyclic ring through N, O, or S, thus the dyestuff H-acid # cresidine # the condensation product from 1 mol. of 2 : 4 : 7-trichloroquinazoline, 1 mol. of H-acid, and 1 mol. of cyclohexylamine gives level blue dyeings on viscose, and, according to the Provisional Specification, the dyestuff H-acid # cresidine # the condensation product from 1 mol. of cyanuryl chloride, 1 mol. of H-acid, 1 mol. of 4-amino-4<1>-oxyazobenzene-3<1>-carboxylic acid, and 1 mol. of aniline gives fast green dyeings. Specifications 14248/07, 5484/08, 248,230, 300,987, 308,958, and 315,451 also are referred to. 1-(4<1>-Methoxybenzoyl)amino - 8 - naphthol-6-sulphonic acid is obtained by reaction of 4-methoxybenzoyl chloride with 1 : 8: 6-aminonaphtholsulphonic acid in presence of an acid-binding agent. 1-Benzoylamino-8-naphthol-4-sulphonic acid is obtained by reaction of benzoyl chloride with 1 : 8 : 4-aminonaphtholsulphonic acid in presence of an acid-binding agent. 1 - (3<1>-Amino-4<1>-methoxybenzoyl-amino-8-naphthol-6-sulphonic acid is obtained by reaction of 3- nitro-4-methoxybenzoyl chloride with 1 : 8 : 6- aminonaphtholsulphonic acid in presence of an acid-binding agent, followed by reduction of the nitro group. 1 - (4<1>-Acetylaminobenzoyl)amino-8-naphthol-6. sulphonic acid is obtained by reaction of 4-nitrobenzoyl chloride and 1 : 8 : 6 - aminonaphtholsulphonic acid in presence of an acid-binding agent, followed by reduction of the nitro group and acetylation of the resulting amino group. 3<1> - Acetylaminophenyl-1 : 2-naphthimidazole-8- oxy-3 : 6-disulphonic acid is obtained by acetylation with acetic anhydride of 3<1>-aminophenyl-1 : 2- naphthimidazole-8-oxy-3 : 6-disulphonic acid prepared by the process of Specification 21175/05. 1-(3<1> - Aminobenzoyl)amino - 8-naphthol-6-sulphonic acid is obtained by reaction of 3-nitrobenzoyl chloride with 1: 8 : 6-aminonaphtholsulphonic acid, followed by reduction of the nitro group. 1 : 4-Dichlorophthalazine is obtained by chlorination with phosphorus oxychloride of the 1 : 4- dihydroxyphthalazine produced by the action of hydrazine on phthalic acid.