Patent GB-191009968-A (GB)
Title: Manufacture of Yellow to Orange Red Azo-dyestuffs.
Inventor: IMRAY OLIVER
IPC: C09B39/00
Filed: 1910-04-23
Granted: 1911-04-20
Abstract: 9968. Imray, O., [Society of Chemical Industry in Basle]. April 23. Samples furnished. Monoazo and disazo dyes are obtained by combining the diazo compounds of sulphonated or non-sulphonated monamines or diamines of the types NH2-Aryl.X.Aryl<1> and NH2-Aryl.X.Aryl<1>NH2, (where Aryl and Aryl<1> = O6H5- or C6H4- or alkyl, alkyloxy, halogen, or nitro derivatives thereof, and where in the case of monoamines X = S -S.CH2-, -S.CO-, -SO,-, -CH2-, -CO-, -OCH2-, -NH-CH2-, -NH.CO-, -NH.CO.NH-, and in the case of diamines X = S, SO2-, -CH2-, -OCH2-, -NH.CH,-, -NH.CO-, -NH.CO.NH-) with a 1-sulphophenyl-3-methyl-5-pyrazolone, or a 1-sulphophenyl-5-pyrazolone-3-carboxylic acid, or a homologue or halogen or nitro derivative thereof, or by combining the diazo compounds of sulphonated amines or diamines of the above type with the corresponding non-sulphonated pyrazolones. The products dye animal fibres yellow to orange-red shades. The following components are specified :- 2- or 4-aminodiphenylthioether, 2-amino-4-sulpho-, 4-amino-2-sulpho-, 2-amino-4<1>-sulpho-, or 4-amino- 4<1>-sulpho-phenylbenzylether, 2- or 4-aminophenylbenzylether, 2- or 4-aminophenylbenzylthioether, 2- or 4-aminophenylbenzoylthioester, 2- or 4-aminodiphenylmethane, 2- or 4-aminobenzophenone, 4- aminophenylbenzylamine, 4-aminophenylbenzoylamine, 3 : 3'- or 4<1>-4<1>-diaminodiphenylsulphone, 2 : 2<1>- or 4 : 4<1> - diaminodiphenothioether, 4 : 4<1>- diaminodiphenylmethane, 3 : 3<1>-dimethyl-4<1>-4<1>-diaminodiphenylmethane, 4 - aminophenyl-3'-aminobenzoylamine, 4 : 4<1> - diaminodipbenylurea ; 1-psulphophenyl-3-methyl-5-pyrazolone, 1-p-sulphophenyl-5-pyrazolone-3-carboxylic acid, 1-p-sulphoo-tolyl- 5-pyrazolone-3-carboxylic acid, 1-phenyl-3- methyl-5-pyrazolone, 1-phenyl-5-pyrazolone-3-carboxylic acid, 1-o-, -m-, or -p-nitrophenyl-3-methyl- 5-pyrazolone, 1-o-, -m-, or -p-nitrophenyl-5-pyrazoloneÀ3-carboxylic acid. o-Aminophenylbenzylether is obtained by condensing o-nitrophenol with benzyl chloride, and reducing the product. 2-Amino-4-sulpho- or 4-amino-2-sulphophenylbenzylether are obtained by condensing o-nitrophenol-p-sulphonic acid or p - nitrophenol-o-sulphonic acid with benzyl chloride and reducing the products. 2- or 4 - Aminophenyl-4<1>-sulphobenzylether are obtained by condensing o- or p-nitrophenol with benzyl chloride, sulphonating, and reducing. 2- or 4-Aminophenylbenzylthioether are obtained by condensing o- or p-nitrothiophenol with benzyl chloride, and reducing. 2- or 4-Aminophenylbenzoylthioester are obtained by condensing o- or p-nitrothiophenol with benzoyl chloride and reducing. 4 Aminophenyl-3<1>-aminobenzoylamine is obtained by condensing p-nitraniline with m-nitrobenzoyl chloride and reducing. 31 : 3<1>-diaminodiphenylsulphone is obtained by treating nitrobenzene with concentrated fuming sulphonic acid, and reducing. 1-o-, -m-, or p - NitrophenylÀ5-pyrazolone-3-carboxylic acid are obtained by condensing o-, m-, or p-nitrophenylhydrazine with ethyl oxalacetate and hydrolyzing. 1-p-Sulpho-o-tolyl-5-pyrazolone-3-carboxylic acid is obtained by condensed o-tolylhydrazine-p-sulphonic acid with ethyl oxalacetate and hydrolyzing.