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    New dyes of the tetrazaporphin series
    92.
    发明专利
    New dyes of the tetrazaporphin series 未知

    公开(公告)号：GB921250A

    公开(公告)日：1963-03-20

    申请号：GB498561

    申请日：1961-02-10

    Applicant: BASF AG

    Inventor： BAUMANN HANS ,  DISTLER HARRY ,  MERKEL KARL ,  TARTTER ARNOLD ,  WEISSAUER HERMANN ,  WERNER HEINZ-ULRICH

    IPC: C09B47/08 ,  C09B62/10

    Abstract: The invention comprises water-soluble or insoluble tetrazaporphin dyes which contain attached via an amino group, at least one group of the formula where X is a hydrazine or an alkyl or acyl substituted hydrazine group and Y is chlorine, bromine, hydroxyl, mercapto, sulphonic acid, a primary, secondary or tertiary amino group, an ether or thioether group or a hydrazine or substituted hydrazine group. The dyes are made by condensing at temperatures of up to 40 DEG C. one mole of cyanuric chloride or bromide in either order with one mole of a tetrazaporphin dye containing at least one primary or secondary amino group and one mole of hydrazine or an alkyl or acyl hydrazine, the remaining halogen atom on the triazine ring if desired being replaced by a hydroxyl group by hydrolysis or by a mercapto, sulphonic acid, a primary, secondary or tertiary amino, an ether, thioether, hydrazine or substituted hydrazine group by treatment at temperatures of up to 100 DEG C. with a metal sulphite or sulphide, ammonia, a primary or secondary amine, an alcoholate or mercaptan or hydrazine or a hydrazine derivative. The methylol compounds of the dyes are made by reaction of the above dyes with formaldehyde. Examples are given. The water-soluble dyes dye and print wool, silk or polycaprolactam fibres and dye leather and paper. The methylol compounds of the dyes and the esters and ethers thereof dye and print textile materials of natural or regenerated cellulose, and these or the dyes themselves may be applied together with hardenable amino-plast forming substances or precursers thereof and possibly with aldehydes such as formaldehyde in the presence of acids or acid-reacting compounds such as ammonium chloride and the fabric then subjected to heat treatment. In examples cotton fabric is dyed with an aqueous solution containing one of the above dyes and either (1) 1:3-dimethylol-5-methyl perhydrotriazone-2 and monoammonium phosphate, or (3) dimethylol-dihydroxyethylene urea and ammonium nitrate, and the fabric is then heated. Specification 827,569 is referred to.

    New diazapolymethine dyestuffs, their production and use
    96.
    发明专利
    New diazapolymethine dyestuffs, their production and use 未知

    公开(公告)号：GB887259A

    公开(公告)日：1962-01-17

    申请号：GB1657960

    申请日：1960-05-11

    Applicant: BASF AG

    Inventor： BAUMANN HANS ,  LEUCHS DIETER

    IPC: C09B27/00 ,  C09B44/20 ,  C21D1/46

    Abstract: The invention comprises dyes of formula where R is an alkyl radical, A the divalent radical of an amine or enamine capable of coupling of which the amino group is joined to -N(+)R1R2R3 by way of an alkylene or arylene radical, X and Y radicals which do not dissociate in aqueous solution and which may be parts of a condensed-on aromatic ring which may be substituted by the equivalent of an anion and R1, R2 and R3 are alkyl radicals which may be substituted and may be united to each other, possibly by way of hetero atoms. The dyes are made by treating a compound of the formula HANR1R2, or an appropriate quaternary ammonium salt thereof, with the required thiazolone-2-hydrazone by the process of Specification 782,310 with subsequent quaternisation if necessary. Illustrative of specified 2-hydrazones are 3-methyl-4-phenyl-, 3-methylbenz- and 3-methyl-6-chlor- and -phenylamino and -acetylamino-benz-thiazolone-2-hydrazones. Representative of specified amines are and Indicated as alkylating agents are alkyl halides, dialkyl sulphates and alkyl esters of organic sulphonic acids. Z(-) may be derived from inorganic, organic or complex acids, e.g. bromide, perchlorate, trichlorzincate, phosphate and oxalate. The dyes colour textile materials of polyacrylonitrile or poly-1,1-dicyanoethylene or copolymers thereof with compounds such as vinyl acetate and chloride and vinylidene chloride. Examples are provided of the preparation of the dyes and their use in colouring processes, blue shades being obtained. Specifications 860,584 and 860,634 also are referred to.

    New cationic azo dyestuffs derived from imidazole and methods for their production and their use
    97.
    发明专利
    New cationic azo dyestuffs derived from imidazole and methods for their production and their use 未知

    公开(公告)号：GB885046A

    公开(公告)日：1961-12-20

    申请号：GB2180659

    申请日：1959-06-25

    Applicant: BASF AG

    Inventor： BAUMANN HANS ,  DEHNERT JOHANNES

    IPC: C09B39/00

    Abstract: The invention comprises dyes having cations of formula where R1 and R2 are H, alkyl, cycloalkyl, aralkyl or aryl or members of a non-aromatic ring, R3 and R4 are alkyl, cycloalkyl or aralkyl, Ar is o- or p-phenylene or o- or p-naphthylene or the divalent residue of 4,41-azo-benzene and X is Hlg, alkoxy, alkylthiol, sulphonic acid, alkyl- or aryl-sulphonic acid ester or R5-N-R6 where R5 is H, free or substituted alkyl, cycloalkyl or aralkyl, R6 is free or substituted alkyl or aryl or R5 and R6 form a heterocyclic ring and of formula where R1, R2, R3 and R4 are as above Ar1 is the divalent residue of a diphenyl compound, preferably of diphenyl, stilbene, diphenyl ether, diphenyl, sulphide or diphenylamine, and X is where R1, R2, R3 and R4 are as above. The dyes may be made by coupling appropriate diazo or tetrazo compounds with the required imidazole with subsequent quaternisation or by coupling a diazo compound of an amine of formula H2N-Ar-Y, where Y is a substituent which may be split off as an anion, e.g. halogen, alkoxy, sulphonic acid or sulphonic acid ester group, with an appropriate imidazole with subsequent quaternisation and, if desired, treatment with an amine of formula R5NHR6, or with an N-substituted carboxylic acid amine, e.g. dialkylformamides, to replace Y. During salt formation other conversions such as hydrolysis, reduction, esterification and etherification may be effected. The dyes may also be made by coupling a diazo compound of an amine of formula H2N-Ar-H with the required imidazole, quaternising and treating the salt with appropriate amines in the presence of oxidising agents. The dyes may be isolated by salting out from acid solution. Indicated as substituents for the dyes are halogen, alkyl, aralkyl, hydroxy, alkoxy, nitro, cyano, amino, acylamino, alkyl- and aryl-sulphone, carboxylic acid and ester, carboxylic acid amide which may be substituted, sulphonic acid amide and arylazo groups. Representative of diazo components specified are 2,5-dichloro- and dimethoxy-anilines, 2-nitro-4-methoxy-aniline, 4 - dimethylaminoaniline, 4 - N - bis - (21 - cyanoethyl) - aniline and 4 - (21 - methoxy) - phenylamino-aniline and of specified imidazoles are imidazole and its 4-methyl, 4,5-diphenyl, 4,5 - pentamethylene, 4 - (41 - dimethylamino) - phenyl and 4 - (41 - dimethylamino) - phenyl derivatives. Usual alkylating agents are employed. Representativ of specified amines used in the last of the above processes are monoethylamine, methyl - 2 - hydroxyethylamine, ethyl - 2 - cyanoethylamine, N,N - dimethyl - 1,3 - diaminopropane, pyrrolidine, hexamethylene imine, piperazine and benzylamine. Conventional oxidising agents are used. The anions may be organic or inorganic, amongst those listed being halogen, sulphate, perchlorate, methosulphate and alkylbenzene sulphonate, and double salts may also be formed, e.g. with zinc chloride. By reaction with acids or acid dyes they may be converted into lacquer or pigment dyes. When soluble in water they colour materials of mordanted cotton, natural or synthetic polyamides, e.g. wool, silk, leather, polyhexamethylene diamine adipate or polycaprolactam, cellulose esters or ethers, polyurethanes, polyesters and especially polyacrylonitriles. Numerous examples are provided of the preparation of the dyes and their use in colouring processes to give various shades of red, blue and yellow. Diazo dyes are obtained from monoazo dyes such as 4-amino-41-dimethylamino-azobenzene, and from 3,31-dimethoxy - 4,41 - diaminodiphenyl and 4,41-diamino-diphenyl and -diphenyl sulphide. Specifications 787,891, 791,932 and 837,472 are referred to.

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