CH303879A - Process for the preparation of an azo dye. - Google Patents
Process for the preparation of an azo dye.Info
- Publication number
- CH303879A CH303879A CH303879DA CH303879A CH 303879 A CH303879 A CH 303879A CH 303879D A CH303879D A CH 303879DA CH 303879 A CH303879 A CH 303879A
- Authority
- CH
- Switzerland
- Prior art keywords
- parts
- dye
- preparation
- azo dye
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 239000000987 azo dye Substances 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims 2
- 239000000975 dye Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- UONVFNLDGRWLKF-UHFFFAOYSA-N 2,5-diaminobenzoic acid Chemical compound NC1=CC=C(N)C(C(O)=O)=C1 UONVFNLDGRWLKF-UHFFFAOYSA-N 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000003086 colorant Substances 0.000 claims description 2
- 150000008049 diazo compounds Chemical class 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 238000007747 plating Methods 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- NRZRRZAVMCAKEP-UHFFFAOYSA-N naphthionic acid Chemical compound C1=CC=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 NRZRRZAVMCAKEP-UHFFFAOYSA-N 0.000 description 2
- 150000002828 nitro derivatives Chemical class 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 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 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- -1 nitromonoazo Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- WSDQIHATCCOMLH-UHFFFAOYSA-N phenyl n-(3,5-dichlorophenyl)carbamate Chemical compound ClC1=CC(Cl)=CC(NC(=O)OC=2C=CC=CC=2)=C1 WSDQIHATCCOMLH-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000009958 sewing Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001256 tonic effect Effects 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
- C09B56/00—Azo dyes containing other chromophoric systems
- C09B56/04—Stilbene-azo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 295051. Verfahren zur Herstellung eines Azofarbstoffes. ES wurde gefunden, dass man zu einem neuen, wertvollen Azofarbstoff gelangt, wenn
EMI0001.0005
worin Z die bei der Kondensation der Nitroverbindung der Formel
EMI0001.0006
mit 2,5-DiaminobenZ0l-1-earborisäure entste hende, stickstoffhaltige Atomgruppierung be deutet, mit 1-(4'-Benzoylamino)-phenyl-3-me- thyl-5-pyrazolon kuppelt.
Der neue Farbstoff stellt ein braunrotes Pulver dar, das sich in konzentrierter Schwe felsäure mit violetter, in Wasser mit oranger Farbe löst und Baumwolle nach dem ein- oder zweibadigen Naehkupferungsverfahren in lichtechten, orangen Tönen färbt, die auch sehr gute Nassechtheiten besitzen.
Die Verbindung der ersten der obenstehenden Formeln lässt sieh auf folgende Art herstellen: Diazotierte 4-Nitro-4'-aminostilben-2,2'-disul- man eine Diazoverbindung des Amins der Formel Tonsäure wird mit 1-Aminonaphthalin-4-sul- fonsäure gekuppelt, hierauf der o-Aminoazo- farbstoff zum Triazol oxydiert und dieses an der Nitrogruppe mit 2,5-Diaminobenzol-l-car- bon.säure kondensiert.
Die für die Herstellung dieses Ausgangs stoffes erforderlichen Umsetzungen können alle in an sich bekannter Weise erfolgen. Die Kupplung mit der 1-Aminonaphthalin-4-sul- fonsäure wird zweckmässig in schwach saurem Medium durchgeführt. Die Oxydation zum Triazol kann durch Erwärmen in Gegenwart von Kupfersalzen erfolgen. Die Kondensation des Nitromonoazofarbstoffes mit der 2,5-Di- aminobenzol-l-carbonsäure nimmt man z. B, durch Erwärmen dieser Stoffe in verdünnter Alkalihydroxydlösung vor.
Die Diazotierung des Amins der eingangs erwähnten Formel erfolgt mit Vorteil nach der sogenannten indirekten Methode, das <I>Beispiel:</I> 63,2 Teile der Verbindung der Formel
EMI0002.0005
werden als Natriumsalz in 500 Teilen heissem Wasser gelöst.
Man gibt eine heisse Lösung von 18 Teilen 2,5-Diaminobenzol-l-carbonsäure in 200 Teilen Wasser und 16 Teilen 30 % iger Na triumhydroxydlösung hinzu, versetzt alsdann mit 80 Teilen 30 % iger Natriumhy droxyd- lösung, kocht 4 Stunden, fällt den Farbstoff mit 80 Teilen Natriumchlorid und filtriert ihn nach dem Erkalten ab.
Er wird auf dem Filter mit 10 % iger Natriumchloridlösung aus gewaschen. 41 Teile des so erhaltenen Natrium salzes des Monoazofarbstoffes werden in 500 Teilen warmem Wasser gelöst, mit 3,
5 Teilen Natriumnitrit als 20 % ige Lösung versetzt und
EMI0002.0023
4o worin Z die bei der Kondensation der Nitroverbindung der Formel
EMI0002.0025
heisst indem man eine einen geringen Alkali- kn aufweisende Lösung eines Alkali salzes der zu diazotierenden Verbindung mit einem Lberschuss an verdünnter Salzsäure ver einigt. unter gutem Rühren auf Eis und 27,5 Teile 30 % ige Salzsäure ausgetragen.
Man lässt einige Stunden unter Kühlung rühren und vereinigt dann mit einer Lösung von 14,7 Teilen 1-(4'- Benzoylamino) - phenyl - 3 - methy l - 5-pyrazolon in 150 Teilen Wasser, 6,9 Teilen 30 % iger Na triumhydroxydlösung und 25 Teilen Natrium- earbonat. Nach beendeter Kupplung wird der Farbstoff abfiltriert und getrocknet.
Additional patent to main patent no. 295051. Process for the production of an azo dye. It has been found that a new, valuable azo dye can be obtained if
EMI0001.0005
wherein Z is the one in the condensation of the nitro compound of the formula
EMI0001.0006
with 2,5-diaminobenZ0l-1-earboric acid, nitrogen-containing atomic grouping be means, coupled with 1- (4'-benzoylamino) -phenyl-3-methyl-5-pyrazolone.
The new dye is a brownish-red powder that dissolves in concentrated sulfuric acid with a violet color, in water with an orange color and colors cotton in lightfast, orange tones using the one or two bath sewing process, which also have very good wet fastness properties.
The compound of the first of the above formulas can be prepared in the following way: Diazotized 4-nitro-4'-aminostilbene-2,2'-disul- man a diazo compound of the amine of the formula Tonic acid is made with 1-aminonaphthalene-4-sulphonic acid coupled, then the o-aminoazo dye is oxidized to the triazole and this is condensed on the nitro group with 2,5-diaminobenzene-1-carbonic acid.
The reactions required to produce this starting material can all be carried out in a manner known per se. The coupling with 1-aminonaphthalene-4-sulphonic acid is expediently carried out in a weakly acidic medium. The oxidation to the triazole can take place by heating in the presence of copper salts. The condensation of the nitromonoazo dye with the 2,5-di-aminobenzene-1-carboxylic acid is taken, for. B, by heating these substances in a dilute alkali hydroxide solution.
The diazotization of the amine of the formula mentioned at the outset is advantageously carried out by the so-called indirect method, the <I> example: </I> 63.2 parts of the compound of the formula
EMI0002.0005
are dissolved as the sodium salt in 500 parts of hot water.
A hot solution of 18 parts of 2,5-diaminobenzene-1-carboxylic acid in 200 parts of water and 16 parts of 30% sodium hydroxide solution is added, 80 parts of 30% sodium hydroxide solution are then added, cooked for 4 hours, and the precipitate Dye with 80 parts of sodium chloride and filtered off after cooling.
It is washed off on the filter with 10% sodium chloride solution. 41 parts of the sodium salt of the monoazo dye thus obtained are dissolved in 500 parts of warm water, with 3,
5 parts of sodium nitrite are added as a 20% solution and
EMI0002.0023
4o wherein Z is the one in the condensation of the nitro compound of the formula
EMI0002.0025
means by combining a low alkali solution of an alkali salt of the compound to be diazotized with an excess of dilute hydrochloric acid. Discharged with thorough stirring on ice and 27.5 parts of 30% hydrochloric acid.
The mixture is stirred for a few hours with cooling and then combined with a solution of 14.7 parts of 1- (4'-benzoylamino) phenyl - 3 - methyl l - 5-pyrazolone in 150 parts of water and 6.9 parts of 30% strength Na trium hydroxide solution and 25 parts of sodium carbonate. When the coupling has ended, the dye is filtered off and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH303879T | 1951-06-14 | ||
| CH295051 | 1951-06-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH303879A true CH303879A (en) | 1954-12-15 |
Family
ID=25691800
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH303879D CH303879A (en) | 1951-06-14 | 1951-06-14 | Process for the preparation of an azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH303879A (en) |
-
1951
- 1951-06-14 CH CH303879D patent/CH303879A/en unknown
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