Azo dyes and their production
    16.
    发明专利

    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

    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.

    Water-soluble azo dyestuffs containing ethene sulphonic acid amide groups

    公开(公告)号:GB875946A

    公开(公告)日:1961-08-23

    申请号:GB3424159

    申请日:1959-10-09

    Applicant: BASF AG

    Abstract: Compounds containing ethenesulphonamide groups are prepared and used in the preparation of azo dyestuffs (see Group IV(c)). Ethenesulphonyl - (3-aminophenyl)-amide is prepared by the reduction of ethensulphonyl-(3-nitrophenyl)-amide (Specification 686,061, Example 5) in aqueous calcium chloride with iron powder. 1 - ethenesulphonamido - 8 - naphthol-3:6-disulphonic acid sodium salt is prepared in solution by treating an aqueous solution of 1-amino-8-naphthol-3:6-disulphonic acid sodium salt with a solution of ethenesulphonyl chloride in acetone. 1-(31-ethenesulphonamidophenyl)-3-methyl-5-pyrazolone is prepared by reacting 1-(31-aminophenyl) - 3 - methyl-5-pyrazolone with carbyl sulphate in 1 : 2-dichloroethane. 4 - amino-41-ethenesulphonylamido-diphenylsulphide is prepared by reacting 4-nitro-1-amino-diphenyl sulphide with carbyl sulphate in 1 : 2-dichloroethane and reducing the nitrocompound with iron powder in aqueous calcium chloride solution. Specification 686,061 is referred to.ALSO:The invention comprises azo dyestuffs containing at least one ethene-sulphonamide group and at least one water-solubilizing group. The dyestuffs may be prepared by the usual diazotization and coupling reactions using suitable components or by acylation of aminoazo dyestuffs with agents which introduce an ethenesulphonyl radical, such as ethene sulphonic acid chloride and bromide and carbyl sulphate. The dyes may be used to dye cellulose, wool, leather, silk and linear polyamides in many shades, the dyeings being fixed by treatment with alkalis and heating. Many examples are described, the components specified including ethenesulphonyl-(3-or 4-aminophenyl)-amide, 4-amino- 41-ethenesulphonyl amido-diphenyl-sulphide or-sulphone or -ketone or -amine and diamino-diphenylmethane; 1-(phenyl or sulphophenyl)-5-pyrazolones, naphthol-sulphonic acids, aminonaphthol-sulphonic acids and N-acyl derivatives thereof, 8-hydroxyquinoline- 4-sulphonic acid and 2-ethenesulphonylamido- 5-naphthol- 7-sulphonic acid. Specifications 686,061, 712,037, 776,265 and 779,781 are referred to.

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