Patent GB-313636-A (GB)
Title: Manufacture of compounds having affinity for cotton
IPC: C09B39/00
Filed: 1928-02-15
Abstract: 313,636. Imray, O. Y., (I. G. Farbenindustrie Akt.-Ges.). Feb. 15, 1928. Substituted azo or azoxy compounds and amines; azo dyes.-Substances having an affinity for cotton are prepared (1) by reducing a sulphonic acid of a mononitrobenzoylated aromatic diamino compound, or a mononitrobenzoylated diamino compound in which the other amino group is substituated by a group which can easily be eliminated, to an azo- or azoxycompound; or (2) by similarly reducing a dinitrobenzoylated diamino compound and converting the nitro-substituted product into the corresponding amino compound. When starting from dinitro compounds the conversion of nitro groups into amino groups may occur during reduction to the azo- or azoxy-compound. When diazotized on the fibre and coupled with pyrazolones, fast yellow shades are obtained. According to examples (1) sodium 1-amino-4-(4<1>-nitrobenzoylamino)-benzene-2-sulphonate is reduced with caustic soda and sodium sulphide or caustic soda and glucose; the resulting yellow compound is absorbed by cotton and gives a greenish yellow when diazotized and coupled with 1-phenyl-3- methyl-5-pyrazolone; (2) sodium 1-formylamino- 4-(4<1>-nitrobenzoylamino)-benzene-3-sulphonate (obtained from 4-amino-1-formylaminobenzene-3-sulphonic acid and 4-nitrobenzoylchloride) is reduced with sodium sulphide and the product hydrolyzed; (3) 1 :4-di-(4<1>- or 3<1>-nitrobenzoylamino)- benzene-2-sulphonic acid [obtained from 4- or 3- nitrobenzoylchloride (2 mols.) and 1: 4-diaminobenzene-2-sulphonic acid respectively is reduced with zinc dust and acetic acid or with alkaline sodium sulphide; the products diazotized on cotton give greenish yellow shades when coupled with 1-phenyl-3-methyl-5-pyrazolone ; (4) sodium 4 : 4'-di - (4<11>-nitrobenzoylamino) - diphenylcarbamide-3: 3<1>-disulphonate is reduced with alkaline sodium sulphide; the resulting product gives greenish yellow shades when diazotized on cotton and developed with 1-phenyl-3-methyl-5- pyrazolone; (5) sodium 1:4-di-(4<1>-nitrobenzoylamino)-naphthalene-6-surphonate (obtained from 1 : 4-diamino-naphthalene-6-sulphonic acid and 4- nitro-benzoylchloride) is reduced with caustic soda and sodium sulphide; the product dyes cotton pale yellow and when diazotized on the fibre and combined with 1-phenyl-3-methyl-5-pyrazolone gives greenish yellow tints; (6) 1-methyl-2- amino - 4 - (4<1>-nitrobenzoylamino)-benzene-5-sulphonic acid dissolved in caustic soda is reduced with glycose, arsenious oxids, sodium sulphide or zinc dust; the resulting product gives a scarlet dyestuff when diazotized and coupled with 2-oxynaphthalene-3 : 6-disulphonic acid; a similar product is obtained from the 'corresponding 3'-nitrobenzoylamino compound; (7) 1-(4<1>-nitrobenzoylamino)-5-aminonaphthalene-3 :-7-disulphonic acid (obtained from 4-mtrobenzoylchloride and 1 : 5- diaminonaphthalene-3 : 7-disulphonic acid) dissolved in caustic soda is reduced with glucose; (8) the product from (6) is treated with 4-nitrobenzoylchloride and the doubly nitrobenzoylated product obtained reduced with caustic soda and sodium sulphide or with zinc dust and acetic acid; the reduced product is absorbed by cotton and when diazotized on the fibre and developed with 1-phenyl-3-methyl-5-pyrazolone gives gree.nish yellow shades. 1 - Methyl - 2 - amino-4-(4<1> or 3<1>-nitrobenzoylamino)-benzene-5-sulphonic acid is obtained by hydrolyzing the product from 3- or 4-nitrobenzoyl chloride and 1-methyl-2-formylamino-4-aminobenzene-5-sulphonic acid.