公开(公告)号：FR1241327A

公开(公告)日：1960-09-16

申请号：FR807212

申请日：1959-10-10

Applicant: BASF AG

Inventor： LANGE GUENTER ,  EBEL FRIEDRICH ,  SCHROEDEL RUDOLF ,  HENSEL WALTER

IPC: C09B62/527

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：GB939857A

公开(公告)日：1963-10-16

申请号：GB3222660

申请日：1960-09-20

Applicant: BASF AG

Inventor： WEISSAUER HERMANN ,  BRAUN WILLY ,  ROHLAND WERNER ,  SCHROEDEL RUDOLF

IPC: C09B1/20 ,  C09B1/26 ,  C09B1/40 ,  C09B62/467

Abstract: The invention comprises water-soluble anthraquinone dyes of the formula A-(NHCOCH2-CH2-OX)n where A is an anthraquinone dye radical, X is hydrogen or the radical of a carboxylic acid, of sulphuric acid or phosphoric acid and n is 1 or 2, and in particular dyes of the formula where Y is hydrogen or a sulphonic acid group, Z is a direct linkage or one of the radicals -CH2CH2-NH-, and X has the meaning given above. The dyes are made by reacting an anthraquinone of the formula A1-(NH2)n where A1 is an anthraquinone dye radical and n is as above, with a compound of the formula Cl-CO-CH2CH2-OR or by reacting an anthraquinone derivative containing sulphonic acid halide groups with aromatic or heterocyclic amines containing beta-hydroxypropionic acid amide groups or esterified beta-hydroxypropionic acid amide groups. When the products contain carboxylic acid ester groups they may be hydrolysed to the hydroxy derivatives which may then be exterified with a carboxylic acid or sulphuric or phosphoric acid. Examples are given. The dyes dye and print textile materials and shaped articles of wool, silk, synthetic linear polyamides and polyurethanes, cellulose and leather.

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：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.

公开(公告)号：BE619784A

公开(公告)日：1963-01-04

申请号：BE619784

申请日：1962-07-04

Applicant: BASF AG

Inventor： SCHROEDEL RUDOLF ,  ROHLAND WERNER ,  WEISSAUER HERMANN ,  WAECHTER RUDOLF

IPC: C09B29/00 ,  F04C

公开(公告)号：GB901546A

公开(公告)日：1962-07-18

申请号：GB4164359

申请日：1959-12-08

Applicant: BASF AG

Inventor： LANGE GUENTER ,  STEUERLE HELMUT ,  SCHROEDEL RUDOLF ,  MUELLER ROLAND ,  FEDERKIEL WILHELM

Abstract: The invention comprises azo dyes derived from a benzenic diazo component and a naphtholic or enolic coupling component which contain at least one b ,g -dihydroxypropyl radical, combined by way of oxygen, which is esterified in the g -position with sulphuric acid or an organic sulphonic acid and which contains altogether at least one of the groups sulphonic, carboxy and sulphuric acid ester. The dyes may be made by treating appropriate dyes, or intermediates, containing a b ,g -dihydroxypropyl group with sulphuric acid or a halide, anhydride, acid sulphate or pyrosulphate thereof, or those containing a sulphonic and/or a carboxylic group and a b ,g -dihydroxypropyl group with an organic sulphonic acid or a halide or anhydride thereof, or by treating appropriate dyes or intermediates containing a b ,g -epoxypropyl group with sulphuric or a sulphonic acid, and, if necessary, the dye is formed by known methods from the intermediates. Preferred dyes are those of formula (D-N=N-E)-(OCH2CHOH.CH2OY)p1 which may have up to 3 sulphonic and/or carboxy groups, where D is a benzene residue, E the coupling component residue, Y a residue of sulphuric or a sulphonic acid and p1 or 2, and where D and E may contain neutral substituents such as methyl, phenyl, ethoxy, chlorine, amino, mono- and di-ethylamino, benzoylamino, cyano, nitro, trifluoromethyl, sulphonamide, carboxylic acid amide and alkylsulphone groups. D or E may also contain additional azo groups. Especially preferred are dyes of formula where A is the dye residue, R an organic radical, X a sulphonic or carboxy group, Z+ a cationic radical, e.g. H, NH4 or K, m O, 1 and 2, n 1 or 2 and q 1 or 2. Dyes with especially valuable tinctorial properties are obtained from diazo components which contain the oxypropyl group but no sulphonic or carboxy groups. Specified sulphonic acids include ethane, vinyl, b -chloroethyl, p-toluene, o-chlorobenzene, naphthalene-2- and diphenyl-p1p1-di-sulphonic acids. When disulphonic acids are used two diazo components may be combined to give a tetrazo component. Acylation of the b hydroxy group takes place to a slight extent. The dyes colour natural and synthetic substances containing carbonamide groups, e.g. leather, wool, silk, polycaprolactam and condensation products of adipic acid and hexamethylene diamine. They are particularly of use on native and regenerated cellulose, e.g. cotton, linen, viscose rayon, hemp and jute. The dyeing of cellulosic materials is preferably effected in conjunction with an alkaline treatment and a thickening agent. Numerous examples are provided for the preparation of the dyes and their use in colouring cotton in red and yellow shades representative of the coupling components used for monoazo dyes being, 2-naphthol, 1-naphthol-4-sulphonic acid, 2-amino-8-naphthol-6-sulphonic acid, 1-acetylamino-8-naphthol-4,6-disulphonic acid, 2-naphthol-3-carboxylic acid p-sulphoanilide, acetoacetate acid anilide and 1-(3-sulphophenyl)-3-methyl-5-pyrazolone and the disazo dye 4-aniline sulphonic acid --> 3-aminophenyl-(b ,g -dihydroxypropyl) ether (sulphuric acid ester) --> 1-(4-sulphophenyl)-3-methyl-5-pipazolone, is also prepared.

公开(公告)号：CA766234A

公开(公告)日：1967-08-29

申请号：CA766234D

Applicant: BASF AG

Inventor： WEISSAUER HERMANN ,  SCHROEDEL RUDOLF ,  WAECHTER RUDOLF ,  ROHLAND WERNER

公开(公告)号：GB985620A

公开(公告)日：1965-03-10

申请号：GB4298963

申请日：1963-10-31

Applicant: BASF AG

Inventor： SCHOELLIG ALFRED ,  SCHROEDEL RUDOLF ,  SASSE HANS-JUERGEN

IPC: C09B47/06 ,  C09B47/12 ,  C09B47/16 ,  C09B67/00 ,  C09B67/22 ,  C09K23/52

Abstract: The invention comprises phthalocyanine pigment mixtures containing from 10 to 20 mol. per cent of a phthalocyanine of the formula wherein Pc is the radical of a phthalocyanine, R1 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, R2 is an unsubstituted or substituted aliphatic hydrocarbon radical or, together with R1, a heterocyclic ring and n is 1, 2, 3 or 4. Examples describe copper chloro-phthalocyanines containing respectively the hydrochlorides of tri-(hexamethylene - aminomethyl) - and tetra-(pentamethylene - aminomethyl) copper phthalocyanines. Specification 761,718 also is referred to.