New monoazo dyestuffs and their metal complexes and processes for the production thereof

    公开(公告)号:GB863915A

    公开(公告)日:1961-03-29

    申请号:GB2544059

    申请日:1959-07-24

    Applicant: BASF AG

    Abstract: The invention comprises dyes of formula : where Ar is a benzene or quinoline residue, A is H, Hlg, alkyl, sulphonic acid, sulphonamide (which may be substituted) or alkyl- or arylsulphone, B is O or S and R an amino or substituted amino group or an aliphatic or aromatic radical, and their metal complexes. The dyes are made in conventional fashion from appropriate aniline or quinoline diazo components and naphthalenic coupling components, coupling being effected under acid conditions. Indicated substituents for the diazo components are :-halogen, alkyl, alkoxy, nitro, acylamino, carboxy and sulphonic acid groups or groups of formula COX or SO2X where X is an alkyl, aryl, amino or substituted amino group. Indicated as metallizable groups in Ar in #s position to N, are chlorine, hydroxy, alkoxy, carboxy, carbalkoxy and sulphonic acid ester. Specified metals are : Cu, Zn, Cr, Co and Ni. Organic compounds which form metal complexes e.g. 8-hydroxyquinoline, may be present during metallization. The dyes colour natural and synthetic polyamides such as wool, polycaprolactam and polyhexamethylene diamine adipate. Examples are provided of the preparation of the dyes and their metal complexes and their use in colouring nitrogenous fibres in a variety of colours. Specification 692,073 is referred to.

    Polyazo dyestuffs
    57.
    发明专利

    公开(公告)号:GB785084A

    公开(公告)日:1957-10-23

    申请号:GB2495755

    申请日:1955-08-31

    Applicant: BASF AG

    Inventor: BAUMANN HANS

    Abstract: The invention comprises dyestuffs of formula where Z is H, Me or phenyl and Ar1 and Ar2 are the same or different aryl residues, each of which has at least one further azo group and both together have at least 2 SO3H groups, and their copper, cobalt and chromium complex compounds. The dyestuffs are made by tetrazolizing appropriate 4,41-diamino-diphenylmethane derivatives and coupling with the required aromatic compounds with subsequent metallization if desired. The metal-free dyestuffs may also be made by coupling one mol. of the tetrazotized diphenylmethane derivative first with an aromatic compound which is free of azo groups but contains at least 2 coupling-directing hydroxy and/or amino groups, and one mol. of the diazo dyestuff thus obtained is coupled with 2 mols. of an aromatic compound which provides the azo component if the disazo dyestuff is free of amino groups but is otherwise the coupling component. Indicated and specified components which may be coupled with the tetrazotized diphenylmethane are resorcinol, 1,3 - diaminobenzene, 1,8 - dihydroxynaphthalene mono- and di-sulphonic acids, 1,6-dihydroxynaphthalene - 3 - sulphonic acid, 3-aminophenol, 3 - hydroxydiphenylamine and 1-amino-8-naphthol and their sulphonic acids. Diazo components indicated for coupling with the disazo dyestuff are aniline, nitroanilines and toluidines, 2,5-dichloroaniline, sulphanilic and metanilic acids, 4-chloroaniline-3- and aniline-2,5- and 4-aminoazobenzene-3,41-di-sulphonic acids, naphthylamines and 1-naphthylamine-4-and 2-naphthylamine-4,8-di-sulphonic acids. Components indicated for coupling with the tetrazolized disazo dyestuff components are naphthols, naphthylamines, aminonaphthols and their sulphonic acids and 1,3-dihydroxy-, -diamino- and -hydroxyamino-benzenes and their N-alkyl or -aryl derivatives. Dyestuffs specified for coupling with the tetrazotized diphenylmethane derivatives are p-nitraniline --> H acid and H acid \sM benzidine --> 2-naphthol-3,6-disulphonic acid. The dyestuffs dye leather in dark brown to black shades. In examples which illustrate the preparation of the dyestuffs, their copper, cobalt and chromium complexes and their use in dyeing leather apart from certain of the above indicated or specified reactants, aniline-2,4-disulphonic acid and 2-naphthylamine - 5,7 - disulphonic acid --> 1-naphthylamine are used as additional azo components for coupling with a disazo dyestuff.

    New reactive metal complex monoazo dyes

    公开(公告)号:GB1069008A

    公开(公告)日:1967-05-17

    申请号:GB3195964

    申请日:1964-08-06

    Applicant: BASF AG

    Abstract: The invention comprises 1 : 1 or 2 : 1 dye: metal complexes of copper, chromium or cobalt with dyes having the general formula wherein Y is Cl or Br, A is a linear or branched C1-C3 alkylene group or a phenylene group which may be substituted by halogen or methyl, B is -CO- or -SO2-, R is hydrogen or C1-C4 alkyl and K is a radical of a coupling component containing at least one sulphonic group and having a hydroxyl or amino group in the ortho-position to the coupling position. Preferably, K is derived from aminonaphthol mono- or disulphonic acids. Other coupling components used are 1-[4-sulphophenyl]-3-methyl - pyrazolone - (5); 2 - aminonaphthalene-5-sulphonic acid, 1-hydroxy-8-benzoylaminonaphthalene - 3,5 - disulphonic acid and 1-[2-methyl - 4 - sulphophenyl] - 3 - methylpyrazolone (5). They are prepared by coupling a diazotized o-amino phenol having the general formula in which Y, A, B and R are defined above with a coupling component as defined and described above, the dyes obtained being treated with a copper, chromium or cobalt salt. Metallization takes place in the aqueous phase at 40-100 DEG C. at pH values of 4 to 8. The dyes may be used for dyeing and printing wool, leather, synthetic polyamides and polyurethanes, and native or regenerated cellulose by the usual reactive dye processes.ALSO:Dyestuff intermediates having the general formula wherein Y is Cl or Br, A is a linear or branched C1-C3 alkylene group or a phenylene group; B is CO or SO2 and R is a C1-C4 alkyl radical are prepared by condensing dichloropyridazonyl carboxylic or sulphonic acid chlorides with amino-phenols and sulphonating, nitrating and finally reducing the nitro groups.

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