Blue quaternary ammonium salts of n-heterocyclic monoazo dyes

    公开(公告)号:GB995040A

    公开(公告)日:1965-06-10

    申请号:GB2558662

    申请日:1962-07-04

    Applicant: BASF AG

    Abstract: The invention comprises blue water-soluble colour salts free from sulphonic acid groups the cations of which are of formula wherein R1 and/or R2 are hydrogen, substituted or unsubstituted alkyl, cycloalkyl, substituted or unsubstituted phenyl or benzyl radicals or from, together with the nitrogen atom, a heterocyclic ring, or in which R1 or R2, besides its connection with the nitrogen atom, is also attached to the p-position of the naphthalene ring, A1 and A2 are substituted or unsubstituted alkyl, benzyl or phenacyl radicals, and the indazole ring may be further substituted and any other alkylatable nitrogen atoms that may be present may have further positive charges. The dyes are prepared by the alkylation, cycloalkylation or aralkylation of monoazo dyes, free from sulphonic acid groups, of formula:-A-N = N-B-N(R1)R2 wherein A is a 3-indazolyl residue which may be substituted, B is a p-naphthylene radical which may be substituted and R1 and R2 are as defined above. The intermediate aminoazo dyes are prepared by the normal coupling procedures. The dyes may be used to colour mordanted cotton, leather, cellulose esters and ethers, polyamides, polyurethanes and preferably polyacrylonitrile. Examples describe the preparation of the dyes. Specification 791,932 is referred to.

    New basic azo dyes
    39.
    发明专利

    公开(公告)号:GB944303A

    公开(公告)日:1963-12-11

    申请号:GB1389561

    申请日:1961-04-18

    Applicant: BASF AG

    Abstract: The invention comprises dyes of the general formula in which R1 denotes a hydrogen atom, an alkyl radical having 1 to 6 carbon atoms, an aralkyl radical or an aryl radical, R2 denotes a hydrogen atom or an alkyl radical having 1 to 6 carbon atoms, R3, R4, R5 and R6 denote hydrogen atoms or substituents which do not impart water solubility, Y denotes the radical of a coupling component free from sulphonic groups and X denotes the equivalent of an anion and a process for the preparation of basic azo dyes, wherein an aminophenyl-hydrazone of the general formula or a salt thereof having the general formula in which R1-R6 and X have the meanings given above is diazotized, coupled with a compound capable of coupling and, if desired, the product is treated with alkylating or aralkylating agents. X may be a Cl-, Br1HSO4-, H2PO4-, ZnCl3-, ZnBr3-, tosylate or CH3OSO3- ion R3-R6 may be alkyl, alkoxy or acyclamino radicals or halogen atoms. Representative of the coupling components specified are 1,3-dihydroxybenzene, 2-hydroxynaphthalene, 2-hydroxy - 8 - acetylaminonaphthalene, aminobenzenes substituted with such groups as 2-hydroxyethyl, cyanoethyl and hydroxyphenyl groups, 3-methyl, 1-phenyl-3-carbethoxy- and 1 - (2 - methylphenyl) - 3 - methylpyrazolones, hydroxyquinolines, imidazoles, 1,1,3 - trimethyl- and 2-methyl indolines and 2-phenylindole. Aminophenylhydrazones and their salts for use as starting materials are obtained by diazotizing aminonitro- or amino-acylaminobenzenes and coupling with methylene compounds of the general formula in which R1, R3 and R4 have the meanings given above, optionally treating the products with alkylating or aralkylating agents and converting the resulting nitro or acylamino compounds to the corresponding amino compounds by reduction or hydrolysis. Specified aminonitro- and aminoacylamino-benzenes include 1-amino-4-nitro- and 1 - amino - 2 - methoxy - 4 - nitro - benzenes, 1 - amino - 4 - formylamino-, -3- and -4-acetylamino-, -4-oxalylamino- and -2,5-dimethoxy -4- acetylaminobenzenes. Examples are furnished. The dyes are especially suitable for dyeing synthetic fibres, e.g. polyethylene terephthalate, polyhexahydroterephthalyl terephthalate, polyacrylonitrile and acrylonitrile-vinyl acetate copolymers.

    New monoazo dyes containing hydrazinyl substituted triazine residues

    公开(公告)号:GB929097A

    公开(公告)日:1963-06-19

    申请号:GB498461

    申请日:1961-02-10

    Applicant: BASF AG

    Abstract: 2-(4,6-Dihydrazino-1,3,5-triazinyl-2)- and 2-[4,6- di(phenylhydrazino)- 1,3,5-triazinyl- 2) -amino- 5-hydroxynaphthalene- 7-sulphonic acids are prepared by condensing cyanuric chloride with an equimolar amount of 2-amino-5-naphthol-7-sulphonic and then reacting the primary condensate with 2 molar proportions of hydrazine or phenylhydrazine. Specifications 842,802 and 872,249 are referred to.ALSO:The invention comprises monoazo dyes which contain attached by way of an amino group at least one group of formula:- wherein X is the radical of hydrazine or a substituted hydrazine and Y is a halogen atom, an amino group, a hydroxyl group, a mercapto group, the radical of hydrazine or a substituted hydrazine, or an aliphatic, cycloaliphatic, araliphatic, aromatic or heterocyclic radical attached by way of an oxygen, sulphur or nitrogen atom to the triazine ring. The dyes are prepared by reacting a trihalo-s-triazine in any sequence with (a) a monoazo dye or an intermediate of such a dye containing a primary or secondary amino group and (b) hydrazine or a substituted hydrazine to form a secondary condensation product, if desired exchanging the final halogen atom by treatment with alkali, ammonia, an amine, alcohol, phenol or mercaptan or hydrazine or hydrazine derivative and when an intermediate has been used converting this into the dye by coupling. The dyes may be treated with formaldehyde to prepare the corresponding methylol compounds as described in Specifications 842,802 and 872,249 and the methylol compounds may also be etherified or esterified. Specified substituted hydrazines include methylhydrazine, N1,N-dimethylhydrazine, acetylhydrazine, phenylhydrazine and its sulphonic acids, maleic acid hydrazide, N-aminoethylurethane, 2,4,6-trihydrazino-1,3,5-triazine, aminoguanidine, hydrazo-dicarboxylic acid amide, pyrazoline, N-aminopiperazine and the compound of formula The dyes may be used to colour natural and synthetic polyamide fibres, leather, paper and, preferably, cellulose. The dyeings may be carried out in the presence of acid substances and hardenable aminoplast-forming substances, possibly together with an aldehyde or a substance yielding an aldehyde, and fixed by a heat treatment. In examples: (1) the monoazo dye 1-aminobenzene-2-sulphonic acid--->2-(8 -hydroxy - 3,6 - disulphonaphthyl - 1 - amino) -4,6-dichloro-s-triazine is reacted with an equimolar amount of hydrazine hydrate; (2) cotton fabric is padded with an aqueous solution containing the dye obtained in (1), 1,3-dimethylol -5-methylperhydrotriazone-(2) and monoammonium phosphate, squeezed out, dried and heated at 145 DEG C. for 8 minutes; (3) a cotton fabric which has been treated with a caustic soda solution is padded with a liquor containing a dyestuff, methylol or methylene ether, the tetramethyl ether of tetramethylolmelamine, the ammonium salt of polyacrylic acid, polyglycol ether, sodium isopropylnaphthalene sulphonate and a mixture of diethanolamine and triethanolamine hydrochlorides, squeezed out and dried and heated on flat frames at 145 DEG C. A dyed crease resistant fabric is obtained. Further examples of the dyes are specified.

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