公开(公告)号：DE1238136B

公开(公告)日：1967-04-06

申请号：DEF0042437

申请日：1964-03-26

Applicant: HOECHST AG

Inventor： SPRINGER DR HARTMUT

IPC: C09B62/517

Abstract: The invention comprises water - soluble phthalocyanine dyes of the formula in which Pc is a metal-containing phthalocyanine radical which may be sustituted by non-water-solubilizing groups, e.g. alkyl, alkoxy, phenyl, benzoyl, phenylsulphonyl or acylamino groups, R1 is H or a 1-5 C alkyl which may be sustituted by water-solubilizing or non-water-solubilizing groups, e.g. -COOH, -SO3H, -OSO3H, halogen, -OH, alkoxy or acylamino, Z is -(CH2)q- or -(CH2)q-NR2-where q is 1-6 and R2 is H or a 1-5 C alkyl and wherein R1 and R2 may be linked together to form a ring, nucleus A may be further substituted, e.g. by -OH, -COOH, -SO3H, alkoxy, acylamino or nitro or halogen, a is 1-4, b is 0-3 and a + b is at least 2 and at most 4. The dyes may be obtained by condensing amines of the formula with phthalocyanine sulphochlorides, converting the product into the acid sulphuric acid ester and, if desired, treating the products with an alkali metal sulphite whereby a proportion of the sulphato groups are converted to sulphonic acid groups. The condensation may be carried out in aqueous or non-aqueous medium in the presence of acid-binding agents; specified non-aqueous vehicles being methanol, dimethylformamide and pyridine. The formation of the sulphato groups may be effected with sulphuric or chlorosulphonic acids or sulphur trioxide or their complex compounds with tertiary amines in a tertiary amine as solvent. The dyes may be employed to colour materials of cellulose, wool, silk leather or linear polyamides, especially cellulose fibres in the presence of an acid-binding agent.ALSO:In examples: (2) N-[-2-nitro-4-(b -hydroxy-ethyl sulphonyl)-phenyl]-ethylene diamine is prepared by reacting ethylene diamine with b -hydroxyethyl - (3 - nitro - 4 - chloro) phenyl sulphone; (5) N-[21-nitro-41-(b -hydroxyethyl sulphony)-phenyl]-piperazine is prepared by reacting piperazine with b -hydroxyethyl-(3-nitro - 4 - chloro) - phenyl sulphone; (6) N-(b - hydroxyethyl) - N1 - [2 - methoxy - 5 - (b 1-hydroxyethyl sulphonyl)-phenyl]-ethylene diamine is prepared by catalytic hydrogenation in the presence of Raney nickel of 1-[21-methoxy - 51 - (b - hydroxyethyl sulphonyl)-phenyl] 3 - (b 1 - hydroxyethyl) - 4,5 - dihydro - 1,2,3 - triazolium chloride, which is obtained by HCl hydrolysis of the monosulphuric acid ester of 1-[21-methoxy-51-(b -hydroxyethyl sulphonyl) - phenyl] - 3 - (b 1-hydroxyethyl) - 4,5 - dihydro - 1,2,3 - triazole, itself made by coupling a diazonium salt of b -hydroxyethyl - (3 - amino - 4 - methoxy-phenyl) sulphone with diethanolamine disulphuric acid ester.

公开(公告)号：DE1192761B

公开(公告)日：1965-05-13

申请号：DEF0026497

申请日：1958-08-27

Applicant: HOECHST AG

Inventor： GREUNE DR HEINRICH ,  SCHNORRENBERG DR WERNER ,  SPRINGER DR HARTMUT

IPC: C09B62/473

公开(公告)号：DE1179317B

公开(公告)日：1964-10-08

申请号：DEF0030688

申请日：1960-03-05

Applicant: HOECHST AG

Inventor： HEYNA DR JOHANNES ,  SPRINGER DR HARTMUT ,  SCHINZEL DR ERICH

IPC: C09B62/503 ,  C09B62/517

Abstract: In an example, (4), the hydrochloride of b -hydroxyethyl - [4 - (b - aminoethyl) - phenyl] - sulphone, containing one molecule of water of crystallization, is made by saponifying with hydrochloric acid b - hydroxyethyl - [4 - (b - acetaminoethyl) - phenyl] - sulphone prepared be reacting 4 - [(b - acetylamino)ethyl]-benzene sulphinic acid with b -chlorethanol or ethylene oxide. In further examples, (5), b -hydroxyethyl-[3-nitro - 4 - (b - aminoethylamino) - phenyl] - sulphone is made by reacting ethylene diamine with b - hydroxyethyl - [(3 - nitro - 4 - chloro) - phenyl] - sulphone in the presence of copper-II-chloride, and (8) the sulphuric acid ester of b -hydroxyethyl - [3 - (41 - aminobenzoylamino) - 4 - hydroxyphenyl]-sulphon is made by esterifying the corresponding hydroxy compound with sulphuric acid.ALSO:The invention comprises water-soluble dyes of the formula in which Pc is a metal-containing phthalocyanine nucleus, X is a direct linkage or a bivalent organic radical, Y is the group -SO2-CH2-CH2-OSO3H or the group -SO2-CH = CH2, the radicals X and Y being meta or para to each other, n and m are each whole numbers from 1 to 3 the sum of n and m being at most 4, and wherein the benzene nucleus A may contain further substituents. A list of bivalent organic radicals is given which includes alkylene, alkyleneimino, phenylene, phenyleneimino, phenylene-oxy, phenylene-sulphonylamino and phenylene-azo radicals. The dyes are made by condensing in an aqueous medium or phthalocyanine sulphonic acid chloride (a) with an amine of the formula in which X, Y and A have the above meanings, or (b) with an amine of the formula in which X and A have the meanings above and esterifying the product with sulphuric acid. When the products contain -SO2-CH2-CH2-OSO3H groups they may, if desired, be treated with an alkali to convert the said groups into -SO2-CH = CH2 groups. The dyes dye and print natural and regenerated cellulose fibres in the presence of alkaline agents in blue to green shades. Specifications 515,637, 712,037, 733,471 and 867,546 are referred to.