Patent GB-523892-A (GB)
Title: Improvements in the manufacture and production of meta-diaza compounds
IPC: C09B5/16
Filed: 1938-09-09
Abstract: 523,892. Meta-diaza compounds; dyes. JOHNSON, G. W. (I. G. Farbenindustrie Akt.-Ges.). Sept. 9, 1938, No. 36404. [Classes 2 (iii) and 15 (ii)] Meta-diaza compounds (pyrimidines) are made by heating α-amino compounds of the anthraquinone series or of higher condensed ring compounds derived from anthraquinone, or o-aminoalkyl- or o-aminoaryl-ketones of the anthraquinone series, with ammonia or aldehydes, or compounds splitting off aldehydes. The aldehydes may be of the aliphatic, aromatic or heterccyclic series, and the reaction is preferable carried out in the presence of water, an alcohol or other diluent, and in the presence of an oxidizing agent, e.g. a nitro compound or sulphonic acid thereof, such as sodium mnitrobenzenesulphonate, arsenic and a cupric salt, ammonium vanadate, oxygen, or air. The products are in part dyestuffs, and in part dye intermediates. In examples (1) Bz1:Bz3- diazabenzanthrone and its Bz2-phenyl derivative are obtained from 1-aminoanthraquinone and formaldehyde or benzaldehyde, (2) 2-, 3-, 4-, or 8-amino-Bz1:Bz3-diazabenzanthrone from 1:2-, 1:3-, 1:4-, or 1:8-diaminoanthraquinone and formaldehyde. (acetaldehyde gives the 2-methyl derivative), (3) 3:5:8:10-tetraazapyrene and 1:3:7:9-tetraazaperylene from 1:4- or 1:5-diaminoanthraquinone and formaldehyde, (4) 4-amino-nitro-Bz1:Bz3-diazabenzanthrone from 1-amino-2-hydroxy-anthraquinone and formaldehyde or hexamethylenetetramine, (5) 2-hydroxy-Bz1:Bz3-diazabenzanthrone and its Bz2-propyl, -pentyl, -hexyl, -phenyl, and furfuryl derivatives from 1-amino-2-hydroxyanthraquinone and formaldehyde, butyraldehyde, hexoic aldehyde, heptoic aldehyde, benzaldehyde or furfural, (6) #-methoxy-4- amino-Bz1:Bz3-diazabenzanthrone, which dyes acetate artificial silk in yellow shades with a greenish fluorescence, from 1:4-diamino-2-methoxyanthraquinone and formaldehyde, (7) 2- hydroxy-Bz2 - phenyl - Bz1:Bz3 - diazabenzanthrone-21-sulphonic- or -carboxylic acids, which dye wool in yellow shades, from 1-amino-2- hydroxyanthraquinone and benzaldehyde-o-sulphonic or carboxylic acids, (8) Bz1:Bz3-diazabenznathrone and its 2-amino- or 2-sulphonic derivatives from 1-aminoanthraquinone-2-sulphonic acid and formaldehyde, (9) 1:3:7:9- tetraazaperylene-4-sulphonic acid from 1:5- diaminoanthraquinone-2-sulphonic acid and formaldehyde, (10) 4-amino-Bz1:Bz3-diazabenzanthrone-2-sulphonic acid (which dyes wool yellow) from 1:4-diaminoanthraquinone-2-sulphonic acid and formaldehyde, (11) 4-anilino- or -p-toluidino-Bz1:Bz3-diazabenzanthrone-2- sulphonic acid from 1-amino-4-anilino (or p-toluidino) -anthraquinone-2-sulphonic acid and hexamethylenetetramine, (12) Bz2-(2<SP>1</SP>- hydroxy) phenyl-Bz1:Bz3-diazabenzanthrone-2- sulphonic acid, which dyes wool yellow shades, from 1-aminoanthraquinone-2-sulphonic acid and salicylaldehyde, (13) Bz1:Bz3-diazabenzanthrone-2-, 3-, or 6-carboxylic acids from 1- aminoanthraquinone-2-, 3- or 6-carboxylic acids and formaldehyde, acetaldehyde gives the corresponding Bz2-methyl derivatives, and corresponding anthraquinone compounds substituted by nitro or hydroxy in the 4- positions give the 4-amino- and 4-hydroxy derivatives, (14) diazaperylene (Example 1 of Specification 479,407) and 6:7-benzo-8:10-diazapyrene from 5- or 4-aminobenzanthrone and formaldehyde, (15) 4- or 5- benzoylamino-Bz1:Bz3-diazabenzanthrone and the Bz2-phenyl derivatives (yellow vat dyes for cotton) from 1-amino-4- or 5- benzoylamino-anthraquinone and formaldehyde or benzaldehyde, (16) 2-methyl-Bz2-phenyl- Bz1:Bz3-diazabenzanthrone from 1-amino-2- methylanthraquinone and benzaldehyde, (17) 1-aminoanthraquinone-2-aldehyde gives with ammonia a vat dye dyeing cotton in violet shades, (18) diphenyltetraazaperylene from 1:5-diaminoanthraquinone and benzaldehyde, (19) 4-amino-Bz2-phenyl-Bz1:Bz3-diazabenzanthrone-2-sulphonic acid from 1-amino-4-bromanthraquinone-2-sulphonic acid and benzaldehyde, (20) products from 4-amino-3<SP>1</SP>-5<SP>1</SP>-dichloranthraquinone-1(N.2:2<SP>1</SP>(N))-1<SP>1</SP>-benzacridone and other 4-aminoanthraquinone benz-and naphthacridones and benzaldehyde, (21) Bz4-methyl or phenyl- or Bz2:Bz4-dimethyl-Bz1:Bz3-diaza- 2:3-benzanthraquinones from 2-amino-3-acetyl- orbenzoyl-anthraquinones and formaldehyde or acetaldehyde ; the corresponding products from propionaldehyde, butyraldehyde, benzaldehyde, anisaldehyde, 1-naphthaldehyde anthraquinone-2-aldehyde and benzanthrone-2- aldehyde are also described, (22) a product from 1:4-diamino-1:1<SP>1</SP>-dianthraquinonylamine and benzaldehyde, (23) the products from 1:4- diamino-2-anthraquinonyl-2<SP>1</SP>:3<SP>1</SP>-anthraquinonethiazole (or oxazole) and p-chlorbenzaldehyde dye cotton in reddish-blue shades from the vat, (24) products from 4- or 5-amino-Py-C-3-carbethoxy-1:9-anthrapyridone, 5-amino-1:9 - (Py- C-phenyl) - anthrapyridazine, 5-amino -1:9 - anthrapyrimidone,1-amino-2-phenylazomethine-C- anthraquinone and formaldehyde or benzaldehyde, (25) 5-amino-Bz2-methyl-Bz1:Bz3-diazabenzanthrone-2-sulphonic acid from 1:5-diaminoanthraquinone-2-sulphonic acid and acetaldehyde, (26) Bz2-phenyl-Bz1:Bz3-diazabenzanthrone-2:2<SP>1</SP> or 2:3<SP>1</SP> or 2:4<SP>1</SP>-dicarboxylic acids from 1-aminoanthraquinone-2-carboxylic acid and benzaldehyde-o, m and p-carboxylic acids, and (27) Bz2-methyl-Bz1:Bz3-diazabenzan throne-2-carboxylic acid from 1-aminoanthraquinone-2-carboxylic acid and acetaldehyde. Specifications 385,295, 429,187, 436,951 and 440,263 also are referred to.