GB2031453A - Chromium complex dyestuffs - Google Patents
Chromium complex dyestuffs Download PDFInfo
- Publication number
- GB2031453A GB2031453A GB7931623A GB7931623A GB2031453A GB 2031453 A GB2031453 A GB 2031453A GB 7931623 A GB7931623 A GB 7931623A GB 7931623 A GB7931623 A GB 7931623A GB 2031453 A GB2031453 A GB 2031453A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dyestuff
- formula
- chromium complex
- chromium
- optionally substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000011651 chromium Substances 0.000 title claims abstract description 25
- 229910052804 chromium Inorganic materials 0.000 title claims abstract description 22
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 9
- 238000004043 dyeing Methods 0.000 claims abstract description 7
- 239000000463 material Substances 0.000 claims abstract description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000001424 substituent group Chemical group 0.000 claims abstract description 4
- 150000001768 cations Chemical class 0.000 claims abstract description 3
- 239000000975 dye Substances 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 150000001844 chromium Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 6
- 239000001257 hydrogen Substances 0.000 abstract description 6
- 239000004952 Polyamide Substances 0.000 abstract description 4
- 229920002647 polyamide Polymers 0.000 abstract description 4
- 210000002268 wool Anatomy 0.000 abstract description 4
- 229910052736 halogen Inorganic materials 0.000 abstract description 3
- 150000002367 halogens Chemical group 0.000 abstract description 3
- 150000002431 hydrogen Chemical group 0.000 abstract description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 2
- 239000010985 leather Substances 0.000 abstract description 2
- 229920002635 polyurethane Polymers 0.000 abstract description 2
- 239000004814 polyurethane Substances 0.000 abstract description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- -1 aminocarbonyloxy Chemical group 0.000 description 5
- VLZVIIYRNMWPSN-UHFFFAOYSA-N 2-Amino-4-nitrophenol Chemical class NC1=CC([N+]([O-])=O)=CC=C1O VLZVIIYRNMWPSN-UHFFFAOYSA-N 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 125000000547 substituted alkyl group Chemical group 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 229910006069 SO3H Inorganic materials 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
- VXPRSYCAPVEFFU-UHFFFAOYSA-N 2-(5-methyl-3-oxo-1h-pyrazol-2-yl)benzenesulfonic acid Chemical compound N1C(C)=CC(=O)N1C1=CC=CC=C1S(O)(=O)=O VXPRSYCAPVEFFU-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- KEOZRIRNDUJXLQ-UHFFFAOYSA-N 2-butyl-5-methyl-1h-pyrazol-3-one Chemical compound CCCCN1NC(C)=CC1=O KEOZRIRNDUJXLQ-UHFFFAOYSA-N 0.000 description 1
- FHXUYFKYRBLZJU-UHFFFAOYSA-N 3-(5-methyl-3-oxo-1h-pyrazol-2-yl)benzenesulfonic acid Chemical compound N1C(C)=CC(=O)N1C1=CC=CC(S(O)(=O)=O)=C1 FHXUYFKYRBLZJU-UHFFFAOYSA-N 0.000 description 1
- KFMFONANHRXJIH-UHFFFAOYSA-N 3-(5-methyl-3-oxo-1h-pyrazol-2-yl)propanenitrile Chemical compound CC1=CC(=O)N(CCC#N)N1 KFMFONANHRXJIH-UHFFFAOYSA-N 0.000 description 1
- ADDLWFWQQZHALP-UHFFFAOYSA-N 3-chloro-5-methyl-4-(5-methyl-3-oxo-1h-pyrazol-2-yl)benzenesulfonic acid Chemical compound N1C(C)=CC(=O)N1C1=C(C)C=C(S(O)(=O)=O)C=C1Cl ADDLWFWQQZHALP-UHFFFAOYSA-N 0.000 description 1
- NHLAPJMCARJFOG-UHFFFAOYSA-N 3-methyl-1,4-dihydropyrazol-5-one Chemical compound CC1=NNC(=O)C1 NHLAPJMCARJFOG-UHFFFAOYSA-N 0.000 description 1
- QGOYCSUFHXJFCI-UHFFFAOYSA-N 3-methyl-4-(5-methyl-3-oxo-1h-pyrazol-2-yl)benzenesulfonic acid Chemical compound N1C(C)=CC(=O)N1C1=CC=C(S(O)(=O)=O)C=C1C QGOYCSUFHXJFCI-UHFFFAOYSA-N 0.000 description 1
- CWJQQASJVVAXKL-UHFFFAOYSA-N 4-(3-Methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl)benzenesulfonic acid Chemical compound O=C1CC(C)=NN1C1=CC=C(S(O)(=O)=O)C=C1 CWJQQASJVVAXKL-UHFFFAOYSA-N 0.000 description 1
- VFMNIJOKAXPZLE-UHFFFAOYSA-N 4-(5-methyl-3-oxo-1h-pyrazol-2-yl)benzenesulfonic acid Chemical compound N1C(C)=CC(=O)N1C1=CC=C(S(O)(=O)=O)C=C1 VFMNIJOKAXPZLE-UHFFFAOYSA-N 0.000 description 1
- JIDVKTFOIRORRL-UHFFFAOYSA-N 4-chloro-3-(5-methyl-3-oxo-1h-pyrazol-2-yl)benzenesulfonic acid Chemical compound N1C(C)=CC(=O)N1C1=CC(S(O)(=O)=O)=CC=C1Cl JIDVKTFOIRORRL-UHFFFAOYSA-N 0.000 description 1
- DOPJNPGPZIJGEZ-UHFFFAOYSA-N 5-methylpyrazol-3-one Chemical compound CC1=CC(=O)N=N1 DOPJNPGPZIJGEZ-UHFFFAOYSA-N 0.000 description 1
- RHBHJNSTEIEPGS-UHFFFAOYSA-N 5-oxopyrazole-3-carboxylic acid Chemical compound OC(=O)C1=CC(=O)N=N1 RHBHJNSTEIEPGS-UHFFFAOYSA-N 0.000 description 1
- TWLMSPNQBKSXOP-UHFFFAOYSA-N 6358-09-4 Chemical compound NC1=CC([N+]([O-])=O)=CC(Cl)=C1O TWLMSPNQBKSXOP-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229910021563 chromium fluoride Inorganic materials 0.000 description 1
- QOWZHEWZFLTYQP-UHFFFAOYSA-K chromium(3+);triformate Chemical compound [Cr+3].[O-]C=O.[O-]C=O.[O-]C=O QOWZHEWZFLTYQP-UHFFFAOYSA-K 0.000 description 1
- GRWVQDDAKZFPFI-UHFFFAOYSA-H chromium(III) sulfate Chemical compound [Cr+3].[Cr+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O GRWVQDDAKZFPFI-UHFFFAOYSA-H 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000001465 metallisation Methods 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- QXYMVUZOGFVPGH-UHFFFAOYSA-N picramic acid Chemical compound NC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O QXYMVUZOGFVPGH-UHFFFAOYSA-N 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- FTBATIJJKIIOTP-UHFFFAOYSA-K trifluorochromium Chemical compound F[Cr](F)F FTBATIJJKIIOTP-UHFFFAOYSA-K 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/14—Monoazo compounds
- C09B45/16—Monoazo compounds containing chromium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Chromium complex dyestuffs of the formula <IMAGE> wherein R and R1 are methyl, carboxyl or carboxamide, X1 and X2 are independently hydrogen or a non- ionic substituent, R2 is hydrogen, halogen or optionally substituted C1-C4 alkyl, R3 is hydrogen C1-C12 alkyl or cycloalkyl, n is 1 to 3 and Me<(+)> is a cation are used for dyeing and printing nitrogen-containing materials, such as wool, silk, leather, polyamides or polyurethanes. The dyeings obtained have good fastness properties.
Description
SPECIFICATION
Chromium complex dyestuffs
The present invention relates to new chromium complex dyestuffs of the formula
wherein R and R, represent a methyl group, a carboxyl group or a carboxamide group, X1 and
X2 independently of one another represent hydrogen or a non-ionic substituent, R2 represents hydrogen, an optionally substituted C,-C4-alkyl radical or a halogen atom, n represents a number from 1 to 3, R3 is hydrogen, a C1-C,2-alkyl radical or a cycloalkyl radical and Me+ is a cation.
Quite generally, the alkyl groups can optionally be further substituted, for example by CN, halogen (Cl and Br), OH, alkoxy, in particular C,-C4-alkoxy, acyloxy or aminocarbonyloxy, it being possible for the amino group to be further substituted by optionally substituted alkyl or aryl, in particular C,-C12-alkyl, or optionally substituted phenyl.
The carboxamide groups can be monosubstituted or disubstituted, for example by optionally substituted alkyl, in particular C,-C4-alkyl.
Examples of suitable substituents X, and X2 are halogen, in particular Cl and Br, NO2 and optionally substituted alkyl or alkoxy, preferably with 1 to 4 C atoms and sulphonamide groups.
The new chromium complex dyestuffs are prepared by a proces in which dyestuffs of the formula
are converted into the 1:1 chromium complex in the manner which is in itself known by reaction with an agent which donates chromium, and this chromium complex is then reacted with the non-metallised dyestuff of the formula (III) or (II) to give the 1:2 Cr complex.
Preferably, the 1:1 Cr complex of the formula (II) is prepared and the dyestuff of the formula (III) is added onto this complex.
The monoazo dyestuffs of the formula (II) or (III) are obtained in a known manner by coupling diazotised, optionally substituted 2-amino-1-hydroxy-4-nitrobenzene to a pyrazolone of the formula (IV)
or to a pyrazolone of the formula (V)
wherein R, R2, R1, R3, X, and X2 have the meaning given.
Examples of suitable pyrazolones of the formula (V) are 3-methyl-pyrazol-5-one, pyrazol-5-one3-carboxylic acid, pyrazol-5-one-3-carboxa mide, 1 -n-butyl-3-methyl-pyrazol-5-one, 1 -(cyanoethyl)3-methyl-pyrazol-5-one and 1 -(bromoethyl)-3-methyl-pyrazol-5-one.
Examples of suitable aminophenols are 4-nitro-2-aminophenol, 4-nitro-6-chloro-2-aminophenol and 4, 6-dinitro-2-aminophenol.
Examples of suitable pyrazolones of the formula (IV) are 1-(4'-sulphophenyl)-3-methyl-pyrazol- 5-one, 1-(3'-sulphophenyl)-3-methyl-pyrazol-5-one, 1 -(2'-sulphophenyl)-3-methyl-pyrazol-5-one, 1 -(2'-chloro-5'-sulphophenyl)-3-methyl-pyrazol-5-one, 1-(2'-chloro-4'-sulphophenyl)-3-methyl-py- razol-5-one, 1(2', 5'-dichloro-4'-sulphophenyl)-3-methyl-pyrazol-5-one, 1 -(2'-methyl-4'-sulpho- phenyl)-3-methyl-pyrazol-5-one, 1-(2'-chloro-6'-methyl-4-sulphophenyl)-3-methyl-pyrazol-5-one, 1 -(2'-methyl-4'.sulphophenyl)-5-pyrazolone-3-carboxylic acid, 1 -(4'-sulphophenyl)-5-pyrazolone3-carboxylic acid and 1-(4'-sulphophenyl)-5-pyrazolone-3-carboxamide.
The dyestuffs of the formula (II) or (III) are converted into the 1:1 chromium complex by customary methods which are in themselves known, for example by reacting the metal-free dyestuff with a salt of trivalent chromium, such as chromium formate, chromium sulphate or chromium fluoride at the boiling point or if appropriate at temperatures in excess of 1 00 C, in an acid medium. Trivalent chromium can also be produced in the reaction mixture from chromium-VI compounds if a reducing agent, such as, for example, glucose, is added at the same time. The metallisation can also be carried out in the presence of organic solvents. It is preferably carried out in organic solvents such as alcohols or ketones, and as far as possible with exclusion of water.
The reaction of the 1:1 chromium complex of the dyestuff of the formula (II) or (III) with the metal-free dyestuff of the formula (III) or (II) respectively is appropriately carried out in an alkaline to weakly acid medium in an open or closed vessel at normal or elevated temperature, for example at temperatures between 50"C and 1 20 C.
The reaction can be carried out in organic solvents, for example alcohols or ketones, or in aqueous solution, whereupon the addition of solvents, such as, for example, of alcohols or dimethylformamide, can in some cases promote the reaction. In general, it is advisable to react as far as possible equivalent amounts of the chromium-containing 1:1 complex and the metalfree dyestuff with one another, the molecular ratio between the metal-free dyestuff and the 1:1 complex appropriately being at least 0.85:1 and at most 1:0.85; as a rule, the effect of an excess of metal-containing dyestuff is less adverse than that of an excess of metal-free dyestuff.
In general, the closer this ratio is to 1:1, the more advantageous is the result.
Instead of single dyestuffs of the formula (II) or (Ill), it is also possible to employ mixtures of corresponding dyestuffs. Interesting shades are frequently obtained in this manner.
The new, chromium-containing mixed complexes obtainable by the above process are advantageously isolated in the form of their salts, in particular alkali metal salts, above all sodium salts, or also ammonium salts or salts of organic amines with a positively charged nitrogen atom, and are suitably for dyeing and printing the most diverse substances, but above all for dyeing nitrogen-containing materials, such as silk, leather and, in particular, wool, and also synthetic polyamide or polyurethane fibres. They are primarily suitable for dyeing from a weakly alkaline, neutral or weakly acid bath, for example a bath containing acetic acid. The dyeings thus obtained are uniform and have a good fastness to light, washing, milling, decatising and carbonising.
Example 1
0.1 mol of a 1:1 Cr complex dyestuff prepared by coupling diazotised 4-nitro-2-aminophenol to 1-(4'-sulphophenyl)-3-methyl-5-pyrazolone and subsequently chroming the coupling product is stirred, in 1.2 1 of water, with 0.1 mol of the monoazo dyestuff prepared by coupling diazotised 4-nitro-2-aminophenol to 3-methyl-5-pyrazolone. The resulting suspension is heated to 90-95"C and the pH is adjusted to 8-8.5 by means of dilute sodium hydroxide solution. The mixture is stirred until the starting dyestuffs can no longer be detected, 1 20 g of potassium chloride are then introduced, the pH is adjusted to 5 with a little acetic acid and the chromium mixed complex dyestuff which has precipitated is filtered off at 65"C. After drying, a dark brown powder which dissolves in water giving an orange-coloured solution and dyes wool and polyamide, from a weakly acid bath, in orange shades with good fastness to light and good fastness to wet processing is obtained.In the form of the free acid, the dyestuff obtained corresponds to the formula
Chromium mixed complex dyestuffs which have similar properties and dye wool and polyamide in orange to bluish-tinged red colour shades are obtained analogously, using the monoazo dyestuff I and II listed in the table.
Example No. Azo dyestuff I Azo dyestuff II 2 1 OH OH N-S gCH3 t N=NCH OWN 0- N=NCH3 93H N 2 H 503K 0(4 OH 3 q LI /N NOE Na H OH 4 > 4 > 3 > ()FNHON#NC N02 \F'N 2 H OOH SOH OH 5 N Nv > 3 > N-N > 3 o2 $ NO U i)rNN3%i:1: 6 No NOa H CL S03H S03H
Example No. Azo dyestuff I Azo dyestuff II 7 011 CH3 NOe HC NOi H NO2 f CH3 ~ 2 H OH 503H OH 8 onFNaN X H3 N~N4CH3 8 CIC113 3 H OH So3H OH CI NNCII2 Cb43 9 N NOa NOe OH SO3H 014 i4W=:o3$COOH f N=Nt 3 10 NOa Noz H SO3H OH OH PH 5 HOg U NOi? H SO11
Example No. Azo dyestuff I Azo dyestuff II 12 iN7O3YNJ CoN11 N0a 13 S03H OH OH DF$IN$o3Y113 two NOW 14 011 so3 OH 0 N=N II zon,N N Ng 9 2 t NOg 15 OH So3 OH CH3 CONH NOz t NOa H S0311
Example No. Azo dyestuff I Azo dyestuff II 16 or 014 1N=N11CONH CoNH I rN NOL! 17 NO 0e H CH3 t CH3 N=NCt HO NOir 2a2CR2CH3 18 0H 503H > N-Nv(CH3 Q *g 19 r N:N N Hh rN C1caar S03
Claims (11)
1. A chromium complex dyestuff of the general formula
in which R and R1 independent of each other denote a methyl group, a carboxyl group or an optionally substituted carboxamide group, X1 and X2 independently of each other denote a hydrogen atom or a non-ionic substituent, R2 denotes a hydrogen atom, an optionally substituted C1 to C4 alkyl radical or a halogen atom, R3 denotes a hydrogen atom or an optionally substituted C1 to C12 alkyl radical, n is 1, 2 or 3 and Meo denotes a cation.
2. A dyestuff according to claim 1 in which, X1 and X2 denote hydrogen atoms.
3. A dyestuff according to claim 1 or 2 in which R3 denotes a hydrogen atom or an optionally substituted C1 to C12 alkyl group.
4. A dyestuff according to any of the foregoing claims in which R2 denotes a hydrogen atom and nis 1.
5. A dyestuff according to any of the foregoing claims in which R and R1 denote methyl groups.
6. A dyestuff according to claim 1 as hereinbefore specifically identified.
7. A process for the production of a dyestuff as claimed in claim 1 in which a dyestuff of the formula
is converted to a 1:1 chromium complex by reaction with a chromium donating agent, and this chromium complex is then reacted with the other dyestuff of formula (III) or (II) to give the 1:2 chromium complex.
8. A process according to claim 7 in which the 1:1 chromium complex is prepared with the dyestuff of formula (II) and that complex is then reacted with the dyestuff of formula (III).
9. A process for the production of a dyestuff as claimed in claim 1 when carried out substantially as described in any one of the Examples.
10. A dyestuff as claimed in claim 1 when produced by the process of any of claims 7 to 9.
11. A process for dyeing or printing a nitrogen-containing material comprising treating the material with a dyestuff as claimed in any of claims 1 to 6 and 1 0.
1 2. A nitrogen-containing material when dyed or printed by the process of claim 11.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782840651 DE2840651A1 (en) | 1978-09-19 | 1978-09-19 | CHROME COMPLEX DYES |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2031453A true GB2031453A (en) | 1980-04-23 |
| GB2031453B GB2031453B (en) | 1982-10-13 |
Family
ID=6049801
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7931623A Expired GB2031453B (en) | 1978-09-19 | 1979-09-12 | Chromium complex dyestuffs |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS5543188A (en) |
| DE (1) | DE2840651A1 (en) |
| FR (1) | FR2436803A1 (en) |
| GB (1) | GB2031453B (en) |
| IT (1) | IT7925773A0 (en) |
| NL (1) | NL7906410A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006082229A2 (en) * | 2005-02-04 | 2006-08-10 | Clariant International Ltd | Cationic antipyrine based azo metal complex dyes for use in optical layers for optical data recording |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102005012730A1 (en) * | 2005-03-19 | 2006-09-21 | Dystar Textilfarben Gmbh & Co. Deutschland Kg | Metal complex dye mixtures |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1101955A (en) * | 1953-06-08 | 1955-10-12 | Ciba Geigy | Metalliferous azo dyes, their preparation and use |
| FR1356566A (en) * | 1963-04-29 | 1964-03-27 | Basf Ag | Chromium complex dyes containing sulfonic acid groups |
| CH589126A5 (en) * | 1974-01-17 | 1977-06-30 | Ciba Geigy Ag | |
| FR2300779A1 (en) * | 1975-02-13 | 1976-09-10 | Ugine Kuhlmann | PROCEDURE FOR L |
-
1978
- 1978-09-19 DE DE19782840651 patent/DE2840651A1/en not_active Withdrawn
-
1979
- 1979-08-24 NL NL7906410A patent/NL7906410A/en not_active Application Discontinuation
- 1979-09-12 GB GB7931623A patent/GB2031453B/en not_active Expired
- 1979-09-17 JP JP11801679A patent/JPS5543188A/en active Pending
- 1979-09-17 IT IT7925773A patent/IT7925773A0/en unknown
- 1979-09-18 FR FR7923197A patent/FR2436803A1/en active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006082229A2 (en) * | 2005-02-04 | 2006-08-10 | Clariant International Ltd | Cationic antipyrine based azo metal complex dyes for use in optical layers for optical data recording |
| WO2006082229A3 (en) * | 2005-02-04 | 2006-11-02 | Clariant Int Ltd | Cationic antipyrine based azo metal complex dyes for use in optical layers for optical data recording |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2436803B1 (en) | 1983-12-02 |
| NL7906410A (en) | 1980-03-21 |
| DE2840651A1 (en) | 1980-03-27 |
| GB2031453B (en) | 1982-10-13 |
| FR2436803A1 (en) | 1980-04-18 |
| JPS5543188A (en) | 1980-03-26 |
| IT7925773A0 (en) | 1979-09-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |