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    New dyes of the tetrazaporphin series
    43.
    发明专利
    New dyes of the tetrazaporphin series 未知

    公开(公告)号：GB1049766A

    公开(公告)日：1966-11-30

    申请号：GB3545363

    申请日：1963-09-09

    Applicant: BASF AG

    Inventor： DEHNERT JOHANNES ,  TARTTER ARNOLD ,  GROSCH WALTER

    IPC: C09B47/26 ,  C09B62/483

    Abstract: The invention comprises tetrazaporphin dyes having the general formula in which Pc is a tetrazaporphin nucleus, R is hydrogen or substituted or unsubstituted alkyl radical, X is an aromatic heterocyclic ring containing in the ring an unsubstituted imino group, the heterocyclic ring may be attached by a substituted or unsubstituted aryleneamino, arylene-sulphonylamino,arylene-carbonylamino, arylene-azo, alkylene or arylene radical which may be fused with the heterocycle, m is 0-5, n is 1-4, p is 0-2, the total of m, n and p amounting to between 2 and 8 inclusive The tetrazaporphin is preferably a phthalocyanine which may be metallized, e.g. copper, nickel or cobalt and iron, aluminium, zinc or chromium. The dyes are obtained by reacting a tetrazaporphin sulphonic acid halide, preferably chloride or bromide, which may contain free sulphonic acid radicals, with an aromatic-heterocyclic amine having an unsubstituted imino group in the ring, and hydrolysing unreacted sulphonic acid halide groups, or by reacting a tetrazaporphin sulphonic acid halide which may contain free sulphonic acid groups, in any sequence with an aromatic-heterocyclic amine containing an unsubstituted imino group in its ring, and with ammonia or any primary amine, and hydrolysing unreacted sulphonic acid halide groups. Aromatic-heterocyclic amines of the above type include, pyrrole, pyrazole, imidazole, triazole and tetrazole derivatives, indole and indazole derivatives are also specified.

    Azo dyes and tetrazaporphin dyes containing beta-sulphonylpropionamide groups and their production
    44.
    发明专利
    Azo dyes and tetrazaporphin dyes containing beta-sulphonylpropionamide groups and their production 未知

    公开(公告)号：GB1000404A

    公开(公告)日：1965-08-04

    申请号：GB1778962

    申请日：1962-05-09

    Applicant: BASF AG

    Inventor： BRAUN WILLY ,  ROHLAND WERNER ,  TARTTER ARNOLD ,  WEISSAUER HERMANN

    IPC: C09B62/78

    Abstract: The invention comprises azo and phthalocyanine dyes of formula wherein A is the radical of an azo or phthalocyanine dye, R1 is a hydrogen atom or a C1-C4 alkyl radical, R is an alkyl, aralkyl or aryl radical and n is at least 1. The dyes are prepared by reacting an acylating agent containing a radical of formula with an azo or phthalocyanine dye or an intermediate suitable for production of such a dye which contains at least one acylatable amino group if an azo dye intermediate is used and at least two acylatable amino groups if a phthalocyanine intermediate is used, to form a beta-sulphonylpropionamide derivative and when an intermediate is used is completed to an azo dye by a coupling procedure or is completed to a phthalocyanine dye by reacting a phthalocyanine containing at least one halogen atom replaceable by a amino group with the said beta-sulphonyl propionamide derivative codtaining at least one acylatable amino groun. The dyes may be used to colour nitrogenous fibres but are preferably used to colour cellulose materials by the usual reactive dye procedures. Examples describe the preparation of mono- and dis-azo and phthalocyanine dyes. Specification 827,569 is referred to.ALSO:4 - Amino - b - phenylsulphonopropionic acid anilide is prepared by treating a mixture of b -phenylsulphonopropionic acid and dimethyl formamide with thionyl chloride adding 4-nitroaniline to the acid chloride solution, recovering the resultant 4-nitro-b -phenylsulphonopropionic acid anilide and catalytically hydrogenating this in methanol solution. Specfication 827,569 is referred to.

    New water-soluble dyes containing substituted acylamino groups
    48.
    发明专利
    New water-soluble dyes containing substituted acylamino groups 未知

    公开(公告)号：GB958746A

    公开(公告)日：1964-05-27

    申请号：GB1432762

    申请日：1962-04-13

    Applicant: BASF AG

    Inventor： EILINGSFELD HEINZ ,  LUETZEL GERHARD ,  ROHLAND WERNER ,  TARTTER ARNOLD ,  WEIDINGER HANS ,  WEISSAUER HERMANN

    IPC: C07D233/56 ,  C09B1/36 ,  C09B43/00 ,  C09B47/08 ,  C09B69/00

    Abstract: The invention comprises dyes of the general formula: in which D denotes the radical of a dye of the azo, anthraquinone or phthalocyanine series, Y denotes a linear or branched unsubstituted or substituted alkylene group having at least two carbon atoms, R1 denotes a hydrogen atom or an alkyl, hydroxyalkyl, halo alkyl, cyanoalkyl, cycloalkyl, aralkyl or aryl radical, R2 denotes a hydrogen atom or an alkyl radical, R3 denotes an aliphatic hydrocarbon radical which may be substituted and/or polyvalent, Z denotes an unsubstituted or substituted ethylene or vinylene group, n denotes a whole number which is greater than 1 and X\sKX denotes an anion of a mineral acid, preferably a chloride or bromide ion. The characteristic heterocyclic radical in the dyes may be derived from polyvinylimidazole. In Examples (4) and (8) anthraquinones of the formula: are reacted with polyvinylimidazole to obtain blue and red dyes and in Example (11) b -chloropropionyl-p-amino-anilide is reacted with polyvinylimidazole and the product is diazotised and coupled with 1-hydroxynaphthalene-4-sulphonic acid to obtain a red dye.ALSO:The invention comprises any dye of the general formula in which D denotes the radical of a dye of the azo, anthraquinone or phthalocyanine series, Y denotes a linear or branched unsubstituted or substituted alkylene group having at least two carbon atoms, R1 denotes a hydrogen atom or an alkyl, hydroxyalkyl, haloalkyl, cyanoalkyl, cycloalkyl, aralkyl or aryl radical, R2 denotes a hydrogen atom or an alkyl radical, R3 denotes an aliphatic hydrocarbon radical which may be substituted and/or polyvalent, Z denotes an unsubstituted or substituted ethylene or vinylene group, n denotes a whole number which is greater than or equal to 1 and X(-) denotes an anion of a mineral acid, preferably a chloride or bromide ion and processes for the preparation thereof wherein (a) a dye or dye intermediate of the general formula in which D1 denotes the radical of a water-soluble dye of the azo, anthraquinone, or phthalocyanine series or the radical of an intermediate of such a dye and A denotes a chlorine or bromine atom is reacted with a compound of the general formula and when a dye intermediate has been used is completed into a dye by diazotization and (or coupling or by condensation or (b) a dye or dye intermediate of the general formula is reacted with an acid halide containing a cation of the general formula and when a dye intermediate has been used the reaction product is completed into a dye by diazotization and/or coupling or by condensation. The initial dyes or dye intermediates preferably contain one or more water-solubilizing groups, e.g. sulphonic, sulphonamide or sulphone groups, The characteristic heterocyclic radical in the dyes may be derived from such compounds as N-vinylimidazole or the N-methyl or N-ethyl derivatives thereof, polyvinylimidazole and N-hydroxyethyl-2-ethylimidazoline. Halo-alkylcarbonamide groups specified are derived from a - and b -bromo- and chloro-propionamides, a -, b - and g -bromo or chlorobutyramides. Among the many starting materials specified are azo dyes such as 1-aminobenzene - 4 - sulphonic acid --> 2 - (b -chloro - propionylamino) - 5 - hydroxynaphtholene - 7 - sulphonic acid and 1 - amino - 3 - (b - chloropropionylamino) - benzene --> 1 - (4-sulphophenyl) - 3 - methylpyrazolone, 1,4-diaminoanthraquinone - 2 - sulphonic acid, reaction products of 1-amino-4-bromanthraquinone - 2 - sulphonic - or 2 - carboxylic acid with aromatic amines such as 1,4-diaminobenzene, 1,3 - diaminobenzene - 4 - sulphonic acid, 4,41 - diamino - diphenylsulphide - 2,21-disulphonic acid, 4,41 - diaminostilbene - 2,21-disulphonic acid, 4,41-diaminodiphenylamine, or aliphatic diamines such as ethylene or propylene diamines, reaction products of leuco-1,4 - diamino - or - dihydroxyanthraquinones with aromatic diamines, e.g. 1,4-diaminobenzene - 2 - sulphonic acid. Examples of suitable pthalocyanine starting materials are mono-, di- or tetrachlorophthalocyanine, tetraphenylsulphonyl - copper phthalocyanine, tetramino - copper phthalocyanine di -, tri - and tetrasulphonic acids, reaction products of halomethyltetrazaporphins with amino phenols or aminophenolsulphonic acids and reaction products of aromatic or aliphatic primary or secondary diamines or their sulphonic acids with tetrazaporphinsulphonic acid halides. Acid binding agents may be employed in the reactions. The dyes are suitable for dyeing and printing materials of wool, silk, synthetic polyamides, polyurethanes, leather and natural or regenerated cellulose. In dyeing cellulose a process including treatment with basic substances and steam or hot air may be used. Examples are furnished.

    New dyes containing dihalopyridazone groups
    50.
    发明专利
    New dyes containing dihalopyridazone groups 未知

    公开(公告)号：GB950698A

    公开(公告)日：1964-02-26

    申请号：GB544162

    申请日：1962-02-13

    Applicant: BASF AG

    Inventor： TARTTER ARNOLD ,  HENSEL HANS RUPRECHT ,  GRASER FRITZ

    IPC: C09B62/12

    Abstract: The compound of the formula: is obtained by reacting 1-(21-aminoethyl)-4, 5-dichloropyridazone -(6)- hydrochloride with m-nitrobenzene-sulphonic acid chloride in presence of aqueous sodium carbonate. The corresponding amine is obtained by reducing the nitro group in the above compound with iron powder acid aqueous acetic acid.ALSO:The invention comprises dyes of the azo, anthraquinone and phtholocyanine series which contain at least once in the molecule the radical of the formula in which D denotes a -SO2- or -CO- group, R denotes a hydrogen atom, an alkyl radical having 1 to 6 carbon atoms, a cycloalkyl radical, an aralkyl radical or an aryl radical, A denotes an alkylene radical with 2 to 6 carbon atoms in the chain, X denotes a chlorine or bromine atom and Y denotes a chlorine or bromine atom. Such dyes are prepared by reacting an acid halide of an appropriate dye or dye precursor with (a) an amine of the general formula or (b) with a hydrazone compound of the general formula and cyclizing the hydrazone derivative obtained by heating to a dihalopyridazone compound or (c) by reacting an appropriate dye or dye precursor which contains at least once the group of the general formula with mucohalic acid and the hydrazone formed as intermediate is cyclized in the reaction mixture or after isolation to form the dihalopyridazone derivative and in each process, (a), (b) and (c), when a dye precursor has been employed as starting material the product is converted to a dye. Of particular interest are dyes of the formulae where E denotes a phenylene, tolylene or diphenylene radical; where Q represents a sulphodiphenylene or a sulphonaphthylene radical; where Pc denotes the radical of copper phthalocyanine, a chlorocopper phthalocyanine with 1-4 chlorine atoms, a phenyl copper phthalocyanine with 1-4 phenyl radicals or nickel phthalocyanine, I denotes a phenylene radical, optionally substituted, D denotes a -SO2- or -CO- group, m denotes 1 or 2, p 1-4, q 1-3 and the sum of p+q 3-6; where L denotes the radical of a diazo component of the benzene or naphthalene series, M denotes the radical of a coupling component of the benzene, naphthalene or pyrazolone series D denotes a -SO2- or -CO- group, the remainder of the radicals in the last four formulae having the meanings given above. The copper, chromium or cobalt complexes of the o,o1-dihydroxyazodyes are also of interest. Examples are furnished. The dyes are suitable for dyeing and printing such materials as wool, silk, synthetic polyamides, leather and natural or regenerated cellulose.

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