公开(公告)号：GB876496A

公开(公告)日：1961-09-06

申请号：GB118359

申请日：1959-01-13

Applicant: BASF AG

Inventor： ROHLAND WERNER ,  STOECKL ERICH

IPC: C09B43/14 ,  C09B43/155 ,  C09B62/53

Abstract: The invention comprises dyes of formula:- where X is the residue of a water-soluble monoazo dye, A is O or S, D is an arylene residue which may be substituted, E is an alkylene radical of 2-4 C atoms and Z is Hlg. The dyes are made by treating an aminoarylsulphonic acid halogen-alkylamide and an appropriate amino azo dye with phosgene, thiophosgene or a chloroformic acid ester. Alternatively the dyes may be made by conventional diazotization and coupling processes. Indicated aminoaryl sulphonic acid halogen alkylamides are aniline, aminodiphenyl and naphthylamine sulphonic acid chlor- or brom-alkylamides which may be substituted in the aryl nucleus with such substituents as alkyl, aryl, aralkyl, hydroxy, alkoxy, aroxy, sulphonic acid, sulphonamide, sulphohalogenalkylamide, nitro and halogen groups. Specified reactants from which the diazo residue is derived include 1, 4-diaminobenzene- 3-sulphonic acid and 1, 4-diamino-3-nitro-benzene. Coupling component residues are derived from amino-phenol and -naphthols and aminophenyl-methylpyrazolones and their sulphonic acids, sulphones and sulphonamides. The new dyes may be used on wool or linear polyamides but are particularly effective on natural or regenerated cellulose, especially when used in conjunction with an acid-binding agent. Numerous examples are provided of the preparation of the dyes and their use in dyeing cotton in red and yellow shades the diazo components used including 1-naphthylamine, 2-naphthylamine- 5-sulphonic acid, 1-acetamino-3-aniline- 4-sulphonic acid and 4-aminobenzoic acid. Specification 868,745 is referred to.

公开(公告)号：FR1225332A

公开(公告)日：1960-06-30

申请号：FR795460

申请日：1959-05-25

Applicant: BASF AG

Inventor： ROHLAND WERNER ,  STOECKL ERICH ,  EISELE JULIUS ,  FEDERKIEL WILHELM

IPC: D06P3/68

公开(公告)号：FR1366438A

公开(公告)日：1964-07-10

申请号：FR944871

申请日：1963-08-16

Applicant: BASF AG

Inventor： DAUBACH EWALD ,  STOECKL ERICH

IPC: C09B67/00

公开(公告)号：FR1365934A

公开(公告)日：1964-07-03

申请号：FR944729

申请日：1963-08-14

Applicant: BASF AG

Inventor： STOECKL ERICH

IPC: C09B67/28

公开(公告)号：GB879073A

公开(公告)日：1961-10-04

申请号：GB1966159

申请日：1959-06-09

Applicant: BASF AG

Inventor： ROHLAND WERNER ,  STOECKL ERICH ,  EISELE JULIUS ,  FEDERKIEL WILHELM

Abstract: The invention comprises dyes of formula:- where A is a naphthol sulphonic acid residue, D is a benzene or naphthalene residue, E a heterocyclic ring containing at least once the group -C=N- and may contain as substituents condensed-on aromatic rings, coloured or uncoloured organic radicals, halogen atoms, primary amino groups and/or hydroxyl groups, G a sulphonic acid halogenalkylamide group attached via S to an aromatic nucleus of the dyestuff and which may be attached to a coloured or uncoloured part of the dye molecule or to the heterocyclic ring, Q a water-solubilizing group, t is 1, y is 1 or 2 and z an integer. The dyes may be made by (1) coupling a benzene or naphthalene compound containing one or two sulphonhalogenalkylamide groups attached to an aromatic residue with a naphthol sulphonic acid containing the heterocyclic residue, (2) as (1) but the diazo component contains the heterocyclic ring and the azo component the sulphonhalogenalkyamide groups, (3) by condensing an azo dye containing the sulphonhalogenalkylamide group or groups and a primary amino group with an appropriate halo derivative of the heterocyclic compound, (4) by coupling an appropriate diazo component with an azo component containing a heterocyclic ring which is substituted with the sulphonhalogenalkylamide groups, (5) as (4) but the diazo component contains the substituted heterocyclic group, (6) by condensing an azo dye which contains a primary amino group with an appropriate halo compound derived from the heterocyclic compound containing the sulphonhaloalkylamide group or groups, (7) by condensing an azo dye having as substituent a residue of an appropriate haloheterocyclic compound, with an arylsulphonhaloalkylamide containing a primary amino group, (8) by reacting phosgene, thiophosgene or a substance serving as such in a reaction with amino groups, in any sequence on the one hand with an arylsulphonhaloalkylamide containing a primary amino group and on the other hand with a compound containing a primary amino group, of an azo dye containing an appropriate heterocyclic substituent to form an unsymmetrical urea or thiourea, (9) by acylating appropriate heterocyclic azo dyes with arylcarboxylic acid halide sulphonic acid halogenalkylamides and (10) by acylating appropriate heterocyclic azo dyes containing a primary amino group with an arylsulphonic acid halide sulphonic acid halogenalkylamide. Particularly preferred are dyes of formula:- and Water-solubilizing groups mentioned are sulphonic, carboxylic and sulphonic acid amide groups. Indicated as heterocyclic residues are quinolines, quinazolines, pyrimidines, phthalazines and sym triazines. Coloured radicals indicated include radicals of azo and other dyes. Uncoloured radicals may be attached to the heterocyclic residue via an -NH-, -O-, or -S- bridge and those indicated include residues of aliphatic, araliphatic and aromatic amines, hyroxyl and sulphydryl compounds, aminocarboxylic acids and their amides and esters and aminosulphonic acids and their amides or sulphones. Indicated arylsulphonhaloalkylamide groups are benzene, diphenyl or naphthalene sulphonic acid chlor- or brom-alkylamides which may contain further substituents in the alkyl group e.g. alkyl, aralkyl, aryl, hydroxyl, alkoxyl, aroxyl, sulphonic acid, sulphonic acid halogenalkylamide, halogen and nitro groups. The dyes dye or print a variety of textile materials e.g. wool, linear polyamides and native and regenerated cellulose. Materials containing groups which react with the haloalkylamide groups may be dyed and printed in the presence of acidbinding agents. Examples are provided of the preparation of the dyes and their use in dyeing cellulosic materials. Red, orange and bluish-red shades are obtained. Representative of dyes produced are aniline- 4-sulphonic acid beta chlorethylamide --> product of equimols of cyanuric chloride and 1-amino- 8-naphthol-3, 6-disulphonic acid or cyanuric chloride and 1-amino- 8-naphthol-4, 6-disulphonic acid and 1-amino- 4-(4-aminobenzene- 3-sulphonic acid)-aminoanthraquinone- 2-sulphonic acid, aniline-3, 5-disulphonic acid and beta chlorethyl-amide --> product of equimolar quantities of cyanuric chloride, aniline- 2-sulphonic acid and 2-amino-8-naphthol- 6-sulphonic acid, (aniline- 4-sulphonic acid beta-chlorethylamide --> 2-amino- 5-naphthol- 7-sulphonic acid) (2 mols) condensed with cyanuric chloride (1 mol) and the product may be treated with aniline, 1-naphthylamine- 5-sulphonic acid beta chlorethylamide --> product from cyanuric chloride (1 mol), 1-amino- 8-naphthol-3, 6-disulphonic acid (2 mols) and aniline (1 mol), 1-(4-aminobenzoylamino)-benzene- 4-sulphonic acid beta chlorethylamide or 1, 4-diaminobenzene mono-acylated with benzene- 1-sulphonic acid chloride- 4-sulphonic acid-beta chlorethylamide --> product from cyanuric chloride (1 mol), aniline- 2-sulphonic acid (1 mol) and 2-amino- 8-naphthol- 6-sulphonic acid (1 mol), the urea from 1, 4-diaminobenzene- 3-sulphonic acid and the carbamic acid chloride from aniline- 4-sulphonic acid beta chlorethylamide and phosgene --> product of cyanuric chloride (1 mol) and 1-amino- 8-naphthol-3, 6-disulphonic acid, 1, 4-diaminobenzene- 3-sulphonic acid acylated with benzoyl chloride- 3-sulphonic acid beta chlorethylamide --> product of cyanuric chloride (1 mol), 1-amino-5-naphthol- 7-sulphonic (1 mol) and aniline- 4-sulphonic acid (1 mol) and aniline --> product of equimols of cyanuric chloride, 1-amino- 8-naphthol-4, 6-disulphonic acid and aniline- 4-sulphonic acid beta chlorethylamide. Specifications 209,723, 797,946, 823,098, 830,847, 868,741, 868,742, 876,496 and 877,678 are referred to.

公开(公告)号：CA624784A

公开(公告)日：1961-08-01

申请号：CA624784D

Applicant: BASF AG

Inventor： TARTTER ARNOLD ,  FEDERKIEL WILHELM ,  ROHLAND WERNER ,  EISELE JULIUS ,  SCHUSTER CURT ,  GRASER FRITZ ,  GEHM ROBERT ,  STOECKL ERICH

公开(公告)号：GB868742A

公开(公告)日：1961-05-25

申请号：GB148059

申请日：1959-01-15

Applicant: BASF AG

Inventor： ROHLAND WERNER ,  STOECKL ERICH

Abstract: The invention comprises dyes of formula:-X(-CO NH-A-SO2NH-D-Z)n where X is an n valent radical of a monoazo dye, A is an arylene residue, D an alkylene radical, preferably of 2-4 carbon atoms, Z is Hlg and n 1 or 2. The dyes are made in conventional fashion from appropriate diazo and coupling components or by treating monoazo dyes containing at least one carboxylic acid halide group with an aminoarylsulphonic acid halogen alkylamide. Indicated sulphohalogen alkylamides are aniline or naphthylamine sulphonic acid chlor- or brom-alkylamides which may contain substituents in the aryl residue such as alkyl, aryl, aralkyl, hydroxy, alkoxy, sulphonic acid, sulphonamide, sulphonhalogenalkylamide, nitro and halogen groups. Representative of specified compounds from which diazo components may be derived are 1-aniline-3- and -4-carboxylic acids and from which coupling components may be derived are 1-phenol-2-carboxylic acid, 1, 3-dihydroxybenzene-4-carboxylic acid and 2-naphthol-3-carboxylic acid. The dyes dye and print wool, silk, linear polyamides and especially natural or regenerated cellulose in the latter case preferably in the presence of an acid binding agent. Examples are provided of the preparation of the dyes and their use in dyeing cotton in red or yellow dyes typical of the compounds from which the diazo components used are derived are 5-nitro-2-amino-1-methoxybenzene, 2-naphthylamine-7-mono- and -6, 8-di-sulphonic acids, and aniline-4-sulphonic acid, typical compounds from which coupling components used are derived being 2-phenol-1-carboxylic acid, aniline-4-sulphonic acid, 2-naphthol-3-carboxylic acid, 1-acetamino-8-naphthol-3, 6-disulphonic acid, 1-naphthol-3-sulphonic acid, 1-naphthylamine-7-sulphonic acid, 2-amino-8-naphthol-3, 6-disulphonic acid and 1-(31-sulphophenyl)-3-methyl-5-pyrazolone. Specification 868,745 is referred to.

公开(公告)号：GB865305A

公开(公告)日：1961-04-12

申请号：GB1745759

申请日：1959-05-22

Applicant: BASF AG

Inventor： ROHLAND WERNER ,  STOECKL ERICH ,  EISELE JULIUS ,  FEDERKIEL WILHELM

Abstract: Aromatic azo dystuff coupling components contain at least once the group:- wherein R represents a hydrogen atom or an alkyl, aralkyl, cycloalkyl, aryl, halogenalkyl or hydroxyalkyl group, A represents an alkylene radical with up to 4 carbon atoms in the chain, which may be branched and/or may contain hydroxyl groups, and X represents a halogen atom, and numerous such coupling components are specified. Examples describe the preparation of coupling components by (1) condensing 1-amino-8-hydroxynaphthalene-3: 6-disulphonic acid with benzoyl chloride-m-sulphonic acid-b -chlorethylamide, (6) reacting 2-amino-5-hydroxynaphthalene-7-sulphonic acid first with chloroformic acid phenyl ester and then with 1-aminobenzene-4-sulphonic acid-b -chlorethylamide to yield an unsymmetrical urea, and (7) condensing benzene-1-sulphonic acid chloride-4-sulphonic acid-b -chlorethylamide with 1-amino-8-hydroxynaphthalene-3: 6-disulphonic acid.ALSO:Fibres and foils of cellulose (including wood veneers) are dyed or printed by applying a coupling component containing at least one group of the formula:- and/or wherein R represents a hydrogen atom or an alkyl, aralkyl, cycloalkyl, aryl, halogenalkyl or hydroxalkyl group, A represents an alkylene radical with up to 4 carbon atoms in the chain, which may be branched and/or may contain hydroxyl groups, and X represents a halogen atom, also applying an acid-binding agent before, together with or after the coupling component, then heating for a short time at 40 DEG -200 DEG C. to fix the coupling component, and finally applying, locally in the case of printing, a diazotized aromatic amine. Specified acid-binding agents are alkali metal or alkaline earth metal hydroxides, carbonates and bicarbonates. Numerous coupling and diazo components are specified. Examples are given.