公开(公告)号：CA697476A

公开(公告)日：1964-11-10

申请号：CA697476D

Applicant: BASF AG

Inventor： ROHLAND WERNER ,  SCHROEDEL RUDOLF ,  TARTTER ARNOLD ,  FEDERKIEL WILHELM

公开(公告)号：CA696663A

公开(公告)日：1964-10-27

申请号：CA696663D

Applicant: BASF AG

Inventor： LUDSTECK DIETER ,  FEDERKIEL WILHELM ,  TARTTER ARNOLD ,  MESCH WALTER

公开(公告)号：CA693072A

公开(公告)日：1964-08-25

申请号：CA693072D

Applicant: BASF AG

Inventor： HENSEL HANS R ,  BAUMANN HANS ,  TARTTER ARNOLD

公开(公告)号：CA680868A

公开(公告)日：1964-02-25

申请号：CA680868D

Applicant: BASF AG

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

公开(公告)号：GB928413A

公开(公告)日：1963-06-12

申请号：GB4473661

申请日：1961-12-14

Applicant: BASF AG

Inventor： TARTTER ARNOLD ,  BLUM ADOLF

IPC: C09B47/32

Abstract: A process for dyeing or printing cellulose textile materials with tetrazaporphin dyes of the formula T-(CH2-X)n in which T is the radical of a copper or nickel tetrazaporphin, X is a quaternary ammonium salt group which in turn bears a sulphonic acid, sulphonic acid amide, sulphonic acid ester or carboxylic acid, carboxylic acid amide, carboxylic acid ester or nitrile group and n is a whole number from 1 to 8, comprises applying the dye in the absence of weakly acid reacting agents and thereafter heating the material in the presence of an alkali at 50 DEG -150 DEG C. whereby an insoluble tetrazaporphin dye is deposited thereon. The said dyes may be used together with vat dyes or reactive dyes and fixed in the way usual for such dyes. Coloured discharges over dischargeable dyeings or coloured resists over aniline black or naphthol bottomings can be obtained by applying a printing paste containing the said dyes, an alkali and a reducing or discharging agent, e.g. sodium formaldehyde sulphoxylate thereafter heating the printed material at 98 DEG -106 DEG C. The specified alkalis are the carbonates and hydroxides of sodium and potassium and among the weakly acid reagents to be excluded are formic, acetic, trichloracetic, citric, lactic and maleic acid and sodium dihydrogen phosphate. Dyestuffs containing as the group X the preferred group may be prepared by reacting a copper or nickel phthalocyanin containing chloromethyl groups with the potassium salt of N,N-dimethylamino acetic acid in water at 90 DEG -95 DEG C. Examples of dyeing and printing, including resist and discharge printing, fabrics of cotton and spun rayon are given. Specifications 633,160, 686,036 and German Specification 843,725 are referred to.

公开(公告)号：GB926377A

公开(公告)日：1963-05-15

申请号：GB2736460

申请日：1960-08-08

Applicant: BASF AG

Inventor： ROHLAND WERNER ,  SCHROEDEL RUDOLF ,  TARTTER ARNOLD ,  FEDERKIEL WILHELM

Abstract: The sulphuric semiester of m- or p-amino-b -hydroxypropionyl-anilide is made by esterifying with chlorosulphonic acid m- or p-amino-b -hydroxypropionyl-anilide obtained by reducing m- or p-nitro-b -hydroxypropionyl-anilide. These are prepared by hydrolysing m- or p-nitro-b -formoxy- or acroyloxy-propionyl-anilides obtained by condensing m- or p-nitraline with b -formoxypropionyl or b -acroyloxypropionyl chlorides. The sulphuric acid semiester of p-amino-b -hydroxypropionyl-anilide is also made by treating with sulphuric acid p-amino-b -acetoxypropionyl-anilide prepared by reduction of p-nitro-b -acetoxypropionyl-anilide obtained by condensing p-nitraniline with b -acetoxypropionyl chloride.ALSO:The invention comprises dyes of the formula:-Z-(D)n where Z is a tetrazaporphin radical which may be further substituted, n is an integer from 1 to 4 and D is a radical of the formula:- where R1 is hydrogen or the radical of sulphuric acid or phosphoric acid, and particularly dyes which in the form of the free acids have the formula:- where A is a tetrazaporphin radical, n is an integer from 1 to 4, m is an integer from 0 to 4, (n+m) is an integer from 1 to 8, D is the group HO3S-O-CH2-CH2CO.NH-and E is a direct linkage, an alkylene group, a group, a -CO-NH-Q- group or an -SO2-NH-Q-group where G is arylene and Q is alkylene or arylene which may contain sulphonic acid groups. The tetrazaporphin radicals include di- and tribenzotetrazaporphins and metal or metal-free phthalocyanines. The dyes are made by treating an amide of the formula:- where R11 is hydrogen or an aliphatic, cycloaliphatic, araliphatic or aromatic radical and Y is a tetrazaporphin radical which may contain up to three additional groups and other substituents, in the presence of an at least stoichiometric amount of water with ammonia, an amine, a hydrazine or hydroxylamine and if desired esterifying the product of the formula with sulphuric acid or phosphoric acid or, when R1 is to be the radical of sulphuric acid, by treating the amide of the Formula VII(a) with 90 to 100% sulphuric acid at temperatures between 0 DEG and 100 DEG C. The dyes may also be made by reacting tetrazaporphins having n exchangeable halogen atoms, e.g. as chlormethyl, sulphonic acid halide or carboxylic acid halide groups, with amines of the formula:- where Y1 is an aryl radical containing an acylatable amino group. Examples are given. The amides of the Formula VII(a) above are made by condensing a tetrazaporphin containing amino groups with b -acyloxypropionic acid halides such as b -formoxy-, b -acetoxy- or b -acroyloxy-propionyl chlorides. The dyes dye and print foils, films and textile materials of wool, silk, polycaprolactam, linear polyamides, natural or regenerated cellulose, leather and paper in blue to green shades. The dyes containing sulphuric acid or phosphoric acid ester groups are reactive with materials of cellulose and polyvinyl alcohol.

公开(公告)号：GB924533A

公开(公告)日：1963-04-24

申请号：GB575261

申请日：1961-02-16

Applicant: BASF AG

Inventor： TARTTER ARNOLD ,  LANGE GUENTER ,  STEUERLE HELMUT

Abstract: p(g -Sulphato-b - hydroxy-propoxy) aniline and m-(g -sulphato-b - hydroxy-propoxy)-acetanilide are made by esterifying with sulphuric acid p(b :g -dihydroxy-propoxy) aniline and m(b :g -dihydroxy-propoxy) acetanilide. 2-Methyl- 5-(g - p-toluenesulphonyloxy-b -hydroxy-propoxy) aniline is prepared by reacting 2:3- epoxypropyl- (3-formylamino-4-methylphenyl) ether with p-toluene sulphonic acid in acetone. 2-Methyl-5-glycidyloxy-formanilide is made by reacting 2-methyl-5-hydroxy-formanilide with epichlorhydrin.ALSO:The invention comprises water-soluble dyes of the tetrazaporphin series which contain at least one ionic water-solubilizing group and at least one b :g -dihydroxypropyl radical attached to a carbon atom by way of an oxygen or sulphur atom or an amino or sulphone group or attached to a carbonyl or sulphonyl group by way of an amino group, which radical is esterified at the g -position by sulphuric acid, phosphoric acid or an organic sulphonic acid. The dyes are made by suitably esterifying a tetrazaporphin containing at least one b :g -dihydroxypropyl radical attached as indicated above, or by treating a tetrazaporphin containing at least one appropriately attached b :g -epoxypropyl radical with sulphuric, phosphoric or an organic sulphonic acid, or by reacting a tetrazaporphin sulphonic or carboxylic acid halide or a halo-triazinyl tetrazaporphin with an aliphatic or aromatic amine containing the esterified b :g -dihydroxypropyl radical described above. The tetrazaporphin starting materials containing the b :g -dihydroxypropyl or b :g -epoxypropyl radicals are made by reacting tetrazaporphin sulphinic acids, mercaptans, hydroxy compounds or amines with a 1-halo-2:3-dihydroxy-propane or with glycide or by reacting them with an epihalohydrin or a glycerol dihalohydrin and converting the halohyadrins obtained to the epoxides and thence if desired to the dihydroxy compounds, or by condensing tetrazaporphin sulphonic or carboxylic acid halides or a halotriazinyl tetrazaporphin with primary or secondary aliphatic or aromatic amines containing the b :g -dihydroxy- or -epoxypropyl radicals. Examples are given. The dyes dye and print leather, wool, silk and materials of polycaprolactam and condensation products of adipic acid and hexamethylene diamine and especially of natural or regenerated cellulose in conjunction with an alkali and heat treatment. Specifications 854,962, 868,285 and 879,244 are referred to.

公开(公告)号：GB924258A

公开(公告)日：1963-04-24

申请号：GB498361

申请日：1961-02-10

Applicant: BASF AG

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

IPC: C09B3/00 ,  C09B62/04 ,  C09B62/06

Abstract: The invention comprises anthraquinone, pyrene-quinone, perylenetetracarlboxylic acid diimide and perinaphthalene-tetracarboxylic acid diimide dyes which contain at least one group of the formula attached by way of an amino group, where X is a hydrazino or substituted hydrazino radical and Y is chlorine, bromine, hydroxyl, sulphhydryl, sulphonic acid, primary, secondary or tertiary amino, an ether or thioether group or a hydrazino or substituted hydrazino radical. The dyes are made by reacting cyanuric chloride or bromide with hydrazine or a substituted hydrazine and an anthraquinone, pyrene-quinone, perylene- or perinaphthalenetetracarboxylic acid diimide dye containing a primary or secondary amino group and preferably containing a water-solubilizing group and then if desired hydrolysing the remaining triazine halogen atom or treating it with a metal sulphite or sulphide, ammonia, a primary or secondary amine, an alcoholate, a mercaptan, hydrazine or a substituted hydrazine. Anthraquinone dyes include those derived from pyranthrone, violanthrone, isoviolanthrone and benzanthrone. Substituted hydrazines specified are methylhydrazine, N:N-dimethylhydrazine,1 acetylhydrazine, phenylhydrazine, phenylhydrazine-3-sulphonic acid, semicarbazide, thiosemicarbazide, aminoguanidine, hydrazo dicarboxylic acid amide, 2:3:6:7:9:10-hexa-aza-decahydronaphthalene, maleic hydrazide, phthalic hydrazide, N-aminoethylurethane, N-aminopiperazine, 2:4:6-trihydrazino-1:3:5-triazine, pyrazoline and hexahydropyridazine. The dyes may be converted to their methylol compounds by reaction with formaldehyde for example at pH 7,5, and thence to the corresponding ethers or esters. Examples are given. The dyes dye and print textile materials of wool, silk or polycaprolactam and dye leather or paper. The methylol compounds or their esters or ethers dye or print textile materials of natural or regenerated cellulose in the presence of hardenable aminoplast-forming substances or their precursors and acids or acid-reacting substances and if desired aldehydes such as formaldehyde. The dyes are then fixed by a heat treatment. In examples (1) cotton fabric is padded with an aqueous solution of a dye of the above formula containing dimethylolethylene urea and ammonium nitrate, heated and washed to give a crease-resistant fabric, or the dimethylol ethylene urea may be omitted; cotton fabric treated with caustic potash solution is padded with an aqueous liquor containing a dye of the above formula, dimethylolbutane diol diurethane, dimethyl dimethylolurea, polyacrylamide, polyethylene diamine, an aqueous suspension of the condensation product of stearic acid and dihydroxyethyl diethylene triamine and ammonium nitrate, dried, schreinerized and heated; (3) cotton fabric is padded with an aqueous solution of a dye of the above formula, 1:3-dimethylol-5-methylperhydrotriazone-(2) and monoammonium phosphate and dried and heated.

公开(公告)号：GB924230A

公开(公告)日：1963-04-24

申请号：GB1503661

申请日：1961-04-26

Applicant: BASF AG

Inventor： TARTTER ARNOLD ,  LUDSTECK DIETER ,  SCHROEDEL RUDOLF

IPC: C09B62/443

Abstract: 3-(4- Chlorbutyn- (2)-ylamino-sulphonyl)-benzoic acid chloride is obtained by refluxing with thionyl chloride the corresponding acid made by reacting benzene-1-carboxylic acid-3-sulphonyl chloride with excess of 1-amino-4-chlorbutyne hydrochloride.ALSO:The invention comprises water-soluble dyes of the formula: where P is the radical of a phthalocyanine derivative, G is -SO2-, -CO- or a sulphonamidophenylene-aminotriazine linkage wherein the sulphon radical is attached to the phthalocyanine derivative radical, R1 is hydrogen or alkyl, A is alkylene or phenylene which may be substituted by sulphonic acid or carboxylic acid groups, E is the radical of an enol capable of coupling, B is the radical of an aromatic diazo component, D is -O-, -S-, amino or ureido, or diaminotriazine group attached via the amino groups, an aminophenylene carbonamido group attached to B via the carbonamido and to X via the amino group, a sulphonamidophenylene carbonamido group attached to B via the carbonamido and to X via the sulphonamido or an amino group attached to B via -SO2- or -CO-, X is or where Y is chlorine or bromine, R2 is hydrogen, chlorine or bromine and n is a whole number from 1 to 4, the dye molecule containing at least one water-solubilizing radical. The dyes are made by reacting a phthalocyanine derivative containing a sulphonic acid halide, carboxylic acid halide or halogentriazinylamino group with an amine of the formula: or with an amine of the formula and then coupling the product with the diazo compound of an amine H2N-B-D-X; or by reacting a derivative of the formula: where Z is hydroxy, mercapto or a primary or secondary amino group, with a compound Y-M-X where M is a direct linkage, an aminotriazine radical attached directly to Y and via the amino group to X, an aminobenzoyl or a benzoylsulphonamido group attached via the amino or sulphonamido to X and via the carbonyl to Y. The enol group E may be derived from pyrazolones, acetoacetamides or benzoylacetamides. Examples are given. The dyes dye and print wool, silk, linear polyamides, leather and, in conjunction with treatment with an acidbinding agent, native or regenerated cellulose materials in green shades.

公开(公告)号：GB915457A

公开(公告)日：1963-01-16

申请号：GB2736360

申请日：1960-08-08

Applicant: BASF AG

Inventor： ROHLAND WERNER ,  SCHROEDEL RUDOLF ,  TARTTER ARNOLD ,  FEDERKIEL WILHELM

IPC: C07F9/09 ,  C09B43/00 ,  C09B62/473

Abstract: N-substituted b -hydroxy-propionamides and esters thereof of formula R1-O-CH2-CH2-CO-NH-Y (I) wherein R1 is hydrogen or the radical of sulphuric, phosphoric or an arylsulphonic acid and Y is a substituted aromatic radical are prepared by (a) partially saponifying an esterified b -hydroxypropionylamide of formula R11-CO-O-CH2-CH2-CO-NH-Y (II wherein R11 is a C1-C4 aliphatic radical with ammonia, an amine, a hydrazine, hydroxylamine or mixtures thereof preferably in the presence of a solvent and, if desired, esterifying the resultant b -hydroxypropionamide with an appropriate acid; (b) heating a compound of formula II wherein R11 is hydrogen with a C1-C5 aliphatic alcohol and if desired esterifying the resultant b -hydroxypropionamide with an appropriate acid or (c) reacting a compound of formula II with 90 to 100% sulphuric acid at 0 DEG -100 DEG C. to give the esters of formula HO3S-O-CH2-CH2-CO-NH-Y The compounds may be used in the preparation of azo dyes (see Group IV(c)). In examples: (1) m- or p-nitroaniline is condensed with diacrylic acid chloride to give diacrylic acid m- or p-nitroanilide which is treated with ammonia in methanol to give b -hydroxypropionyl-m-or-p-nitroanilide which is reduced to b -hydroxypropionyl-m-or-p-aminoanilide and esterified with chlorosulphonic acid to give the sulphuric acid ester of b -hydroxypropionyl - m-or-p - aminoanilide (b -hydroxypropionyl-p-nitroanilide is also converted into its p-toluene-sulphonic acid ester); (2) as in (1) p-chloroaniline is converted successively into diacrylic acid p-chloroanilide and b -hydroxypropionyl-p-chloroanilide; (3) 2-methoxy-4-nitroaniline or 2-amino-5-naphthol-7-sulphonic acid is acylated with b -acetoxypropionylchloride to give the corresponding amide which is treated as in (1) to give b -hydroxypropionyl-(4-nitro-2-methoxyphenyl)amide, which is reduced to b -hydroxypropionyl - (4 - amino - 2 methoxyphenyl)-amide, and 2 - b hydroxypropionylamino-5 - naphthol - 7 - sulphonic acid; (4) m- or p-nitroaniline are acylated with b -formyloxypropionyl chloride to give b -formyl oxypropionyl-m- or p-nitroanilide which is treated as in (1) to yield b -hydroxypropionylm- or p-nitroanilide; (5) b -formyloxypropionylp-nitroanilide or -2-methoxy-4-nitroanilide is refluxed in methanol to give b -hydroxypropionyl-(4-nitro- or 4-nitro-2-methoxy-phenyl) amide; (6) hydrogenation of b -formyloxypropionyl-p-nitroanilide with Raney nickel and hydrogen in methanol solution under pressure gives b -hydroxypropionyl-p-aminoanilide; (7) b -formyloxy- or -acetoxy-propionyl-p-nitroanilide is reduced to b -formyloxy- or -acetoxypropionyl-p-aminoanilide which is reacted with sulphuric acid to give the sulphuric acid ester of b -hydroxypropionyl-p-aminoanilide; (8) as in (7) the b -acetoxypropionyl derivative of 2-amino-5-naphthol-7-sulphonic acid is converted into the sulphuric ester of 2-b -hydroxypropionylamino-5-naphthol-7-sulphonic acid.ALSO:Monoazo dyes containing b -hydroxypropionamide groups and ester derivatives thereof of formula R1-O-CH2-CH2-CO-NH-Y wherein R1 is hydrogen or the radical of phosphoric, an arylsulphonic or, preferably, sulphuric acid and Y is a monoazo dye residue are prepared by (a) partially saponifying an esterified b -hydroxypropionamide of formula R11-CO-O-CH2-CH2-CO-NH-Y (II) wherein R11 is a C1-C4 aliphatic radical with ammonia, an amine, a hydrazine, hydroxylamine or mixtures thereof, preferably in the presence of a solvent and, if desired, esterifying the resultant b -hydroxypropionamide; (b) heating a compound of formula II wherein R11 is hydrogen with a C1-C5 aliphatic alcohol and if desired esterifying the resultant b -hydroxypropionamide or (c) reacting a compound of formula II with 90 to 100% sulphuric acid at 0 DEG -100 DEG C. to give the esters of formula HO3S-O-CH2-CH2-CO-NH-Y. The dyes may also be prepared in the usual way from diazo and/or coupling components containing the groups, prepared by the above methods (see Group IV(b)). The invention also comprises the dyes of formulae:- 1-phenyl-3-methyl-5-pyrazolone; (2) the aminoazo dye obtained by saponification of the dye 1-amino-4-acetylaminobenzene --> 1-naphthol-4-sulphonic acid is acylated with diacrylic acid chloride, the acyl derivative treated with ammonia to give the b -hydroxypropionylamino-derivative which is esterified with chlorosulphonic or sulphuric acid; (3) the aminoazo dye used in (2) is reacted with b -formyloxypropionyl chloride and the acyl derivative is refluxed with methanol to give the b -hydroxypropionylamino-azo dye which may be esterified with sulphuric acid or heated with sulphuric acid to give the sulphuric acid ester. Further examples are given.