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    Azo dyes and their production
    52.
    发明专利
    Azo dyes and their production 未知

    公开(公告)号：GB954140A

    公开(公告)日：1964-04-02

    申请号：GB2558562

    申请日：1962-07-04

    Applicant: BASF AG

    Inventor： SCHROEDEL RUDOLF ,  ROHLAND WERNER ,  WEISSAUER HERMANN ,  WAECHTER RUDOLF

    IPC: C09B29/00

    Abstract: 3-Amino-b -phenoxypropionic anilide, the corresponding b - methoxy compound and 4-amino-b -phenylmercapto-propionic anilide are obtained by hydrogenating the corresponding nitro compounds using a Raney nickel catalyst. 2-amino-5-hydroxynaphthalene-7-sulphonic acid is amidated with b -phenoxypropionic chloride.ALSO:The invention comprises azo dyes of the formula in which A denotes the radical of an azo dye which may contain one or more sulphonic acid groups, R1 is a hydrogen atom or an alkyl radical having from 1 to 5 carbon atoms, R denotes an alkyl radical, a cycloalkyl radical or an aryl radical, X denotes an oxygen atom or a sulphur atom and n is the number 1 or a number greater than 1. The dyes are produced by reacting an acylating agent which yields a radical of the formula with an azo dye or an intermediate suitable for the production of an azo dye, which contains at least one acylatable amino group to form a b -(propionamide) ether or thioether derivative and, when an intermediate has been used, completing the preparation of the azo dye in a conventional manner. Acylating agents specified include acid halides or anhydrides of such compounds as b -methylmercapto- or b -methoxypropionic acid, b -phenoxy or b -phenyl thiopropionic acids optionally substituted in the phenyl group with substituents such as chloro, methyl, methoxy and nitro groups. The acylating agents are reacted with the dyes or intermediates in aqueous solution or suspension or in organic solvents and the usual inorganic and organic acid binding agents. Representative of the large number of dyes described in examples are those obtained by coupling diazotised 3-amino-b -phenoxypropionic acid anilide with 1 - hydroxynaphthalene - 4 - sulphonic acid, 1 - (3 - sulphophenyl) - 3 - methylpyrazolone, 1 - (6 - chloro - 2 - methyl - 4- sulphophenyl) - 3 - methyl pyrazolone, 1 - benzoyl or - acetylamino - 8 - hydroxynaphthalene - 3,6-disulphonic acid and by coupling diazotised 4-amino - b - phenylmercaptopropionic acid anilide with 1-(2-chloro-5-sulphophenyl)-3-methylpyrazolone or 1 - hydroxynaphthalene - 4 - sulphonic acid. The products are suitable for dyeing or printing wool, silk, synthetic linear polyamides or polyurethanes, paper and textiles of natural or regenerated cellulose.

    New anthraquinone dyes
    58.
    发明专利
    New anthraquinone dyes 未知

    公开(公告)号：GB930774A

    公开(公告)日：1963-07-10

    申请号：GB146561

    申请日：1961-01-13

    Applicant: BASF AG

    Inventor： WEISSAUER HERMANN ,  ROHLAND WERNER ,  LUDSTECK DIETER

    Abstract: 3-Chloro-4-sulphato-butene-(2)-ylamine sulphate, 4-sulphato-butene-(2)-ylamine sulphate and 4-sulphato-butine-(2)-ylamine sulphate are made by treating the hydrochlorides of 3 - chloro - 4-hydroxy-butene-(2)-ylamine, 4-hydroxy-butene- (2)-ylamine and 4-hydroxy-butene-(2)-ylamine with concentrated acid. 3 : 4-Dichloro-butene-(2)-ylamine hydrochloride is made by treating with hydrogen chloride 3 : 4-dichlorobutene-(2)-yl p hexamethylene tetrammonium chloride obtained by mixing hexamethylene tetramine with 1 : 3 : 4-trichlorobutene-(2). 4-Hydroxy-butene-(2)-ylamine hydrochloride is similarly made by using 1-chloro-butene-(2)-ol-(4)-instead of 1 : 3 : 4-trichloro-butene-(2). 4-Aminobenzene sulphonic acid-(4-sulphato-butine-(2-ylamide) sulphate and 4-aminobenzene sulphonic acid-(4-bromo-butine-(2)-ylamide) hydrobromide are made by treating with sulphuric acid amino benzene sulphonamide containing a group -CH2YCH2X where X is chlorine, bromine or sulphato attached to the amide nitrogen atom, or with an amine of the formula H2NCH2YCH2X1 where X1 is chlorine, bromine, sulphato or hydroxyl and when X1 is hydroxyl converting it to a sulphate ester group and when X1 is chlorine or bromine reacting it, if desired, with a tertiary amine or with tetramethyl-thiourea.ALSO:The invention comprises dyes of the formula F-(CH2-Y-CH2-X)n in which F is the radical of a dye derived from an anthraquinone, n is 1 or 2, Y is one of where Hal is chlorine or bromine X is chlorine or bromine, an -OSO3H group, a quaternary ammonium radical or an isothiouronium radical, and in which formula the radical -CH2-Y-CH2-X is attached to the nitrogen atom of a -CONH-, an alkylamino or dicarboxylic acid imide group of the anthraquinone dye. The radical F may be derived from amino-anthraquinones and particularly from 1-amino-4-arylamino-anthraquinone-2-sulphonic acid. The dyes may be made by reacting an anthraquinone containing a halogenoalkyl, carboxylic acid halide, sulphohalide, carboxylic acid anhydride or imide or a group with an aqueous hydrobromic acid respectively 4-amino benzene sulphonic acid-(4-hydroxy-butine-(2)-ylamide) hydrochloride, which is obtained by reacting 4-acetamido benzene sulphonyl chloride with 4-hydroxybutine-(2)-ylamine hydrochloride in the presence of caustic soda and then treating with hydrochloric acid. 3-carboxy benzene sulphonic acid-(3:4-dichlorobutene-(2)-ylamide) is made by treating benzoic acid-3-sulphochloride with 3:4-dichlorobutene-(2)-ylamine hydrochloride. The corresponding acid chloride is made by treatment of the acid with thionyl chloride.

    New azo dyes containing halomethylbenzoylamino- or halomethylbenzenesulphonylamino-groups
    59.
    发明专利
    New azo dyes containing halomethylbenzoylamino- or halomethylbenzenesulphonylamino-groups 未知

    公开(公告)号：GB917764A

    公开(公告)日：1963-02-06

    申请号：GB2860960

    申请日：1960-08-18

    Applicant: BASF AG

    Inventor： ROHLAND WERNER ,  MESCH WALTER ,  LUDSTECK DIETER ,  FEDERKIEL WILHELM

    Abstract: 1 - (4-chloromethylbenzoylamino)-8-naphthol-3:6-disulphonic acid and 1-(4-chloromethylbenzoylamino) - 4 - aminobenzene-3-sulphonic acid are prepared by reacting 1-amino-8-naphthol-3:6-disulphonic acid or 1:4-diaminobenzene-3-sulphonic acid with 4-chloromethylbenzoyl chloride.ALSO:The invention comprises azo dyes of formula wherein A is the residue of a diazo component of the benzene, naphthalene, phenylazobenzene and phenylazonaphthalene series, B is the residue of a coupling component of the benzene, naphthalene, 1-arylpyrazole and phenylazonaphthalene series, Y is a -CO- or -SO2- group and X is a chlorine or bromine atom. They are prepared by reacting an aminoazo dye of formula:- with a halomethyl-benzenesulphonyl- or benzoyl-halide or by diazotisation and coupling using appropriate components. The dyes may be used to dye and print wool, silk, synthetic polyamides and cellulose fibres, particularly cotton, in a variety of shades, the dyeing being fixed by treatment with an acid-binding agent. The dyes may also be prepared on the fibre by diazotisation and coupling. In examples: (1) the dye 1-(4-chloromethylbenzoylamino)- 4-aminobenzene-3-sulphonic acid --> 1-amino-8-naphthol-3:6-disulphonic acid is prepared; (2) the dye 1-acetylamino-4-aminobenzene-3-sulphonic acid --> 1-naphthol-4-sulphonic acid is prepared, hydrolysed with hydrochloric acid and the resultant aminoazo dye condensed with 4-chloromethyl-benzoyl chloride; (3) an aqueous solution containing sodium hydroxide and 1-(4- chloromethylbenzoylamino)- 8- naphthol-3:6-disulphonic acid is applied to cotton fabric which is then dried and heated to the coupling component and the treated fabric padded with a diazo solution of sulphanilic acid to give a violet dyeing. Many further examples are specified.

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