Patent GB-324041-A (GB)
Abstract: 324,041. Carpmael, A., (I. G. Farbenindustrie Akt.-Ges.). Oct. 15, 1928. Diazoamino compounds are made (1) by causing any diazo compound to interact with a primary amine of the benzene series containing a sulphonic and a carboxylic group or two or more carboxylic groups, (2) by coupling a diazo compound containing at least one negative substituent with a water soluble polylnuclear primary amine which does not form azo-dyestuffs (e.g. 1-naphthylamine-2 : 4-disulphonic acid), (3) by causing any diazo compound to react with an aromatic mono- or polynuclear primary amine containing one or more sulphamino groups (not forming azodyestuffs), (4) by causing an energetically coupling negatively substituted diazo compound to interact with a primary amine of the benzene series containing two or more sulphonic acid groups. On treatment with acid they are reconverted into the diazo compounds and are useful in dyeing, printing and also for combating insect pests. In examples diazoamino compounds from the following reagents are described : (1) diazotized m-chloraniline, sulphanilic acid or 4-chlor- 2-toluidine and 2-amino-4-sulphobenzoic acid, (2) diazotized 4-chlor-2-toluidine and 3-amino-5-sulphobenzoic acid or 3-amino-5-sulpho-4-hydroxybenzoic acid or 5-amino-3-sulpho-2-hydroxybenzoic acid or their alkyl ethers, (3) diazotized 4-chlor- 2-toluidine and 2-amino-5-sulphobenzoic acid or sulphonic acids of 4-aminobenzoic acid, e.g. 4- amino-3-sulphobenzoic acid, or 5-sulpho-4-msthyl- 3-aminobenzoic acid, or 4-amino-2-sulpho-oxanilic acid, (4) diazotized o-chloraniline and 1-amino benzene-3 : 5-dicarboxylic acid or 3-(or 4)- aminobenzene-1 : 2-dicarboxylic acid, (5) diazotized 4- chlor-2-anisidine, 4-(or 5)-nitro-2-toluidine, 3- nitro-4-toluidine, 3-, 5-, or 6-chloro-2-toluidine, 3-chloro-4-toluidine, 4 :5- or 4 :6-dichloro-2- toluidine, 3 : 6-dichloro-4-toluidine, 6-nitro-4- methoxy-3-toluidine, 6-benzoylamino-4-chloro-3- amino-1-methoxybenzene or 2 :5-dichloroaniline and 2-amino-4-sulphobenzoic acid; as diazo components other amines of the benzene, naphthalene, diphenyl or heterocyclic series e.g. aminocarbazoles, aminoanthraquinones e.g. 1-amino- or 1-amino-4-benzoylaminoanthraquinone or aminoazo compounds, e.g. p-aminoazotoluene may be used (6) diazotized 5-chloro-2-toluidine or 4-nitro- 1-naphthylamine and 2-amino-5-sulphobenzoic acid, (7) diazotized 5-nitro-2-toluidine and aniline- 2 : 5- or 2 : 4-disulphonic acid, (8) diazotized 3- nitro-4-toluidine or 2 :4-dinitroaniline and aniline- 2:5- or 3 :5-disulphuric acid, (9) diazotized 2- aminocarbazole or 1-aminoanthraquinone and 4- sulpho-2-aminobenzoic acid, (10) diazotized 3- nitro-4-toluidine and 1-naphthylamine-2 : 4-disulphonic acid, (11) diazotized 2 : 5-dichloraniline or 1-chlor-2-naphthylamine and 2-napht-hylamine- 4 : 6 : 8-trisulphonic acid, (12) diazotized mchloraniline and 2-naphthylamine-6 : 8-disulphonic acid or 2-naphthylamine-8-sulphonic acid, (13) diazotized m-chloraniline or 2 :5-dichloraniline and 4-toluidine-2-sulphanilide, (14) diazotized pnitraniline and the 5<1>-amino-2<1>-methylanilide of benzenesulphonic acid. Sulphamino compounds are made by reducing the condensation products from nitroamino compounds and aromatic sulphochlorides e.g. that from 4-nitro-2-toluidine and benzene sulphochloride. Aminosulphohydroxybenzoic acids and alkyl ethers thereof.-3-amino-5-sulpho-4-hydroxybenzoic acid is made by sulphonating p-hydroxybenzoic acid, nitrating and reducing to 5-amino-3- sulphosalicyclic acid similarly from salicylic acid. The alkyl ethers are made by treating the sodium salt of the acid with an alkylating agent. 5-Sulpho-4-methyl-3-aminobenzoic acid is made by sulphonating p-toluic acid, nitrating and reducing. 6-Benzoylamino-4-chlor-3-amino-1-methoxybenzene is made by benzoylating 5-nitro-4-chlor-2- amino-1-methoxybenzene and reducing. 4-Amino-2-sulphooxanilic acid is made by sulphonating p-nitraniline-oxamic acid and reducing.