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    Dyes of the tetrazaporphin series and their production
    208.
    发明专利
    Dyes of the tetrazaporphin series and their production 未知

    公开(公告)号：GB926377A

    公开(公告)日：1963-05-15

    申请号：GB2736460

    申请日：1960-08-08

    Applicant: BASF AG

    Inventor： ROHLAND WERNER ,  SCHROEDEL RUDOLF ,  TARTTER ARNOLD ,  FEDERKIEL WILHELM

    Abstract: The sulphuric semiester of m- or p-amino-b -hydroxypropionyl-anilide is made by esterifying with chlorosulphonic acid m- or p-amino-b -hydroxypropionyl-anilide obtained by reducing m- or p-nitro-b -hydroxypropionyl-anilide. These are prepared by hydrolysing m- or p-nitro-b -formoxy- or acroyloxy-propionyl-anilides obtained by condensing m- or p-nitraline with b -formoxypropionyl or b -acroyloxypropionyl chlorides. The sulphuric acid semiester of p-amino-b -hydroxypropionyl-anilide is also made by treating with sulphuric acid p-amino-b -acetoxypropionyl-anilide prepared by reduction of p-nitro-b -acetoxypropionyl-anilide obtained by condensing p-nitraniline with b -acetoxypropionyl chloride.ALSO:The invention comprises dyes of the formula:-Z-(D)n where Z is a tetrazaporphin radical which may be further substituted, n is an integer from 1 to 4 and D is a radical of the formula:- where R1 is hydrogen or the radical of sulphuric acid or phosphoric acid, and particularly dyes which in the form of the free acids have the formula:- where A is a tetrazaporphin radical, n is an integer from 1 to 4, m is an integer from 0 to 4, (n+m) is an integer from 1 to 8, D is the group HO3S-O-CH2-CH2CO.NH-and E is a direct linkage, an alkylene group, a group, a -CO-NH-Q- group or an -SO2-NH-Q-group where G is arylene and Q is alkylene or arylene which may contain sulphonic acid groups. The tetrazaporphin radicals include di- and tribenzotetrazaporphins and metal or metal-free phthalocyanines. The dyes are made by treating an amide of the formula:- where R11 is hydrogen or an aliphatic, cycloaliphatic, araliphatic or aromatic radical and Y is a tetrazaporphin radical which may contain up to three additional groups and other substituents, in the presence of an at least stoichiometric amount of water with ammonia, an amine, a hydrazine or hydroxylamine and if desired esterifying the product of the formula with sulphuric acid or phosphoric acid or, when R1 is to be the radical of sulphuric acid, by treating the amide of the Formula VII(a) with 90 to 100% sulphuric acid at temperatures between 0 DEG and 100 DEG C. The dyes may also be made by reacting tetrazaporphins having n exchangeable halogen atoms, e.g. as chlormethyl, sulphonic acid halide or carboxylic acid halide groups, with amines of the formula:- where Y1 is an aryl radical containing an acylatable amino group. Examples are given. The amides of the Formula VII(a) above are made by condensing a tetrazaporphin containing amino groups with b -acyloxypropionic acid halides such as b -formoxy-, b -acetoxy- or b -acroyloxy-propionyl chlorides. The dyes dye and print foils, films and textile materials of wool, silk, polycaprolactam, linear polyamides, natural or regenerated cellulose, leather and paper in blue to green shades. The dyes containing sulphuric acid or phosphoric acid ester groups are reactive with materials of cellulose and polyvinyl alcohol.

    New azo dyestuffs containing dihalogenpyridazone groups
    210.
    发明专利
    New azo dyestuffs containing dihalogenpyridazone groups 未知

    公开(公告)号：GB924660A

    公开(公告)日：1963-05-01

    申请号：GB2218060

    申请日：1960-06-24

    Applicant: BASF AG

    Inventor： HENSEL HANS RUPRECHT ,  BAUMANN HANS ,  DURY KARL ,  FEDERKIEL WILHELM

    IPC: C09B62/16

    Abstract: Pyridazone compounds used in the preparation of azo dyes (see Group IV(c)) are prepared by heating hydrazines with mucochloric or mucobromic acid. Nitro and acylamino groups in the pyridazone compounds may be converted into amino by reduction or hydrolysis, the nitro groups being introduced by nitration of the pyridazone compounds in some cases. Compounds prepared in this manner in examples are 1-(31-nitro- or -acetylamino- or -amino-phenyl)-4:5-dichloropyridazone-(6), 1-(4-acetylamino- or -amino-phenyl)-4:5-dichloropyridazone-(6), 1-(3-amino-6-sulphophenyl)-4:5-dichloro- or -dibromo-pyridazone-(6), 1-(4-methyl-2- or -3-aminophenyl)-4:5-dichloropyridazone-(6), 1-[41-(411-nitro- or -amino-211-sulpho-styryl)-31-sulphophenyl] - 4:5-dichloropyridazone-(6), 1-(4-sulphophenyl)- or -(2-nitro-or -amino-4-sulphophenyl)-4:5-dichloropyridazone-(6) and 1-(2-methoxy-4-amino-5-sulphophenyl)-4:5-dichloropyridazone-(6). Further compounds are prepared by condensing the acid chloride of 1-(4-carboxyphenyl)-4:5-dichloropyridazone-(6) with various amino compounds. Products specified in examples are 1-X-8-naphthol-3:6-disulphonic acid, 6-X-1-naphthol-3-sulphonic acid and 3-or 4-X-6-sulpho-aniline wherein x is a 4-(4:5-dichloro-6-keto - pyridazinyl) - benzoylamino group. Intermediate hydrazones prepared in examples are the 3-acetylaminophenyl- and 3-acetylamino - 6 - sulphophenyl - hydrazones of mucochloric acid. 1- (41- aminobenzenesulphonamidophenyl)-4 : 5-dichloropyridazone-(6) is repared by condensing 1-(4-aminophenyl)-4:5-dichloropyridazone-(6) with 4-acetylaminobenzensulphonyl chloride followed by hydrolysis of the amino group. 41-nitro-4-hydrazino-stilbene-2:21-disulphonic acid is prepared by diazotisation of the corresponding 4-amino-compound and reduction of the diazo compound with stannous chloride and hydrochloric acid. The acid chloride of 1-(4-carboxyphenyl)-4 : 5-dichloropyridazone-(6) is prepared by heating the acid with thionyl chloride in nitrobenzene.ALSO:The invention comprises dyes of formula wherein A is the radical of an aromatic or arylazoaromatic diazo component, B is the radical of an aliphatic, aromatic, arylazoaromatic or heterocyclic coupling component including a component of the tetrazaporphin series and in which only one of the radicals A and B is an arylazoaromatic radical, D is a direct covalent linkage, group, X is a chlorine or bromine atom and n is 1 or 2; and metal complexes thereof. The dyes are prepared by diazotization and coupling procedures using suitable components. Specified metal complexes are copper, chromium and cobalt complexes prepared by known methods. The dyes may be used for dyeing and printing wool, synthetic polyamides and cellulose fibres in conjunction with an acid-binding agent. In examples: (1) the dyestuff 1-(4-aminophenyl)-4, 5-dichloropyridazone-(6)-->1-(2-methyl-4- sulphophenyl) -3-methyl-5-pyrazolone is prepared; (2) the dyestuff 1-(3-amino-6-sulphophenyl)-4:5-dichloropyridazone --> 1 - naphthol - 4 - sulphonic acid is coppered oxidatively; (3) the dyestuff 1-(4-methyl-2-aminophenyl)-4, 5-dichloropyridazone - (6) --> 2 - amino - 4 - acetylaminobenzenesulphonic acid-->1-(2-chloro-5-sulphophenyl)-3-methyl-5-pyrazolone is prepared; (4) 1-(3-amino-6-sulphophenyl) - 4, 5 - dichloropyridazone-(6) is diazotized and coupled with the compound of formula Many further examples are specified. Specification 660,447 is referred to.

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