Azomethine chromium complex dyes derived from pyrazolone sulphonic acids

    公开(公告)号:GB1148107A

    公开(公告)日:1969-04-10

    申请号:GB3476066

    申请日:1966-08-03

    Applicant: BASF AG

    Abstract: 1,148,107. Chromium complexes of azomethine dyes. BADISCHE ANILIN- & SODAFABRIK A.G. 3 Aug., 1966 [4 Aug., 1965; 5 Aug., 1965], No. 34760/66. Heading C4P. The invention comprises chromium complexes of azomethine dyes of the general formula wherein Ar is a phenyl or naphthyl radical which bears a hydroxyl or alkoxy group ortho to the N atom of the azomethine link and which may be further substituted, R 1 is an alkyl or aryl group and benzene ring I may bear non- ionic substituents, e.g. halogen, alkyl, aryl, alkoxy or nitro groups. They are prepared by reacting the corresponding benzene or naphthalene primary amine ArNH 2 with an appropriate 1-sulphophenyl-pyrazolone 5-aldehyde(4) or the 4-aldimmonium salt of the aldehyde with simultaneous or subsequent action of a chroming agent. Conventional chroming agents are used in 0À5 to 1À3 equivalents per mol of dye at 80‹ to 130‹ C. in presence of water, monohydric alcohols, polyhydric alcohols or acid amides.

    New anthraquinone dyes
    18.
    发明专利

    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

    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

    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

    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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