Patent GB-465484-A (GB)
Title: Manufacture of diazoamino-compounds soluble in water
Filed: 1935-11-07
Abstract: Diazoamino compounds of aminoazo compounds, of the general formula <FORM:0465484/IV/1> where R<111> is an aromatic or heterocyclic radicle, R<11> is the radicle of an amine capable of being coupled, R<1> is hydrogen, alkyl, oxyalkyl, aralkyl, aryl or hydroaryl, and R is an aliphatic, araliphatic, aromatic, hydroaromatic or heterocyclic radicle containing solubilizing groups, e.g. carboxylic, sulphonic or hydroxy groups, or R and R<1> jointly denote the radicle of a heterocyclic ring of which the nitrogen is the hetero-atom and which contains solubilizing groups, are manufactured by combining a diazo-compound with a diazoamino compound <FORM:0465484/IV/2> obtained from the diazo compound of an amine which, in its non-diazotized form is capable of being coupled with diazo compounds to form aminoazo compounds, and a nitrogen base soluble in water. The products are intermediates for the manufacture of dyestuffs.  In examples: (1) 1-amino-2 : 5-dimethoxybenzene is diazotized and combined with sarcosine, and diazoamino compound is coupled with diazotized p-nitraniline; (2) 1-amino-3-methoxy-4-methylbenzene is diazotized and combined with methyltaurine, and the diazoamino compound is dispersed in water with the aid of the condensation product of octodecyl alcohol with ethylene oxide and is coupled with diazotized 1-amino-2-chloro-4-nitrobenzene; (3) the diazoamino compound from diazotized a -naphthylamine and 1-methylaminobenzene - 2 - carboxylic - 4-sulphonic acid is coupled with diazotized 1-amino - 2 - ethoxybenzene; (4) the diazo amino compound from diazotized 1-amino-2-methoxy-5-methylbenzene and sarcosine is coupled with diazotized 1-amino-2-nitro-4-methylbenzene.  A table gives the properties of further diazoamino compounds, the following additional components being specified: diazo components R<111>NH2: 1-amino-2 : 6-dichloro-4-nitrobenzene, 1-amino-2-methyl-3, 4- and 5-chlorobenzene, 1-amino-4-chloronaphthalene, o- and m-nitraniline, 1-amino-2 : 5-dichlorobenzene, 1-amino-2-chloro-5-trifluoromethyl - benzene, 1-amino-2-nitro-4-methoxybenzene, 1-amino - 2 : 4 - dichloro - 6 - nitrobenzene, 1 - amino - 3 - trifluoromethylbenzene, 1-amino - 2 - nitro - 4 - trifluoromethylbenzene, 2 - amino - 1 - nitronaphthalene, 1 - amino-4-methoxybenzene, 1 - amino - 2 - methoxy - 4-and 5 - nitrobenzene, 1 - amino - 2 - methoxy-4- and 5-chlorobenzene, 1 - amino - 2 - and 3-chlorobenzene, 1 - amino - 5 - trifluoromethylphenyl - 2 - ethylsulphone, 1 - amino - 2-methyl - 4 - nitrobenzene, 1 - amino - 3 : 5-bis - trifluoromethylbenzene, 1 - amino - 2-methoxybenzene - 5 - sulphonic acid diethylamide, 1 - amino - 3 - methyl - 4 : 6 - dichlorobenzene, 1 - amino - 2 - trifluoromethyl - 5-chlorobenzene, 1 - amino - 3 - benzoylamino-4 : 6 - dimethylbenzene, 2 : 4 and 2 : 5-dichloraniline, 1 - amino - 2 - methyl - 4 : 5-dichlorobenzene, 2-amino-diphenyl sulphone, 1 - amino - 4 - benzoylamino - 2 - methoxy - 5-methylbenzene, 1 - amino - 2 - nitro - 4-methoxybenzene, 1 - amino - 4 - benzoylamino-2 - chloro - 5 - methoxybenzene, 1 - amino - 4-benzoylamino - 2 : 5 - dimethoxybenzene, 1 - amino - 4 - chloro - 2 - nitrobenzene, 1-amino - 2 : 4 - dinitrobenzene; amines R<11> NH2 : 1 - amino - 3 - methoxy - 4- and 6-chlorobenzene, 1 - amino - 3 - methoxy - 5-bromobenzene, 1 - amino - 3 : 4 - dimethoxybenzene, 1-amino-2- and 5-methoxynaphthalene, 1 - amino - 2 - methylnaphthalene, 1-amino - 2 - methyl - 5 - methoxybenzene, 1 - amino - 3 - methoxybenzene, 1 - amino-2 : 5 - diethoxybenzene, 1 - amino - 3 - ethoxy-4 - methylbenzene, 1 - amino - 4 - methyl-2 : 5 - dimethoxybenzene, 1 - amino - 4-chloro - 2 : 5 - dimethoxybenzene, 1 - amino-4 - bromo - 2 : 5 - diethoxybenzene, 1 - amino-2 : 4 : 5 - trimethoxybenzene, 2 - amino - 4-methoxynaphthalene, 1 - amino - 3 - ethoxybenzene, 1 - amino - 4 - benzoylamino - 2 : 5-dimethoxy- and diethoxybenzene; nitrogen bases NHRR<1>: proline, 1-methylamino and ethylamino - 2 - hydroxypropane - 3 - sulphonic acid, 1 - aminobenzene - 2 - carboxylic acid 4- and 5 - sulphonamide, hydroxyethylaminoacetic acid, pipecolinic acid, 1 - methylaminobenzene - 2 - carboxylic - 5 - sulphonic acid, cyanamide, piperidine - a  - and b  - sulphonic acid, n - butylaminoacetic acid, 1 - aminobenzene - 2 - carboxylic - 4- and 5 - sulphonic acid, aniline - 2 : 5 - disulphonic acid, methylglucamine, piperazinoacetic acid, hydroxyethyltaurine, pyrollidine - a  - sulphonic acid, ethylenediaminediacetic acid, piperidine-b -carboxylic acid, phenyglycine-3 - sulphonamide, 5 - aminofurane - 2 - carboxylic acid, cyclohexylaminoacetic acid, 1-methylaminohexahydrobenzene - 3 - sulphonic acid, 1-aminonaphthalene - 2 : 4 - disulphonic acid, b -g -dihydroxypropylaminoacetic acid.