Patent GB-958746-A (GB)
Title: New water-soluble dyes containing substituted acylamino groups
Inventor: EILINGSFELD HEINZ
IPC: C09B69/00
Filed: 1962-04-13
Abstract: The invention comprises dyes of the general formula: <FORM:0958746/C3/1> 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: <FORM:0958746/C3/2> 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 <FORM:0958746/C3/1> 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 <FORM:0958746/C3/2> 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 <FORM:0958746/C3/3> 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 <FORM:0958746/C3/4> is reacted with an acid halide containing a cation of the general formula <FORM:0958746/C3/5> 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.