CH280184A - Process for the preparation of a trisazo dye. - Google Patents
Process for the preparation of a trisazo dye.Info
- Publication number
- CH280184A CH280184A CH280184DA CH280184A CH 280184 A CH280184 A CH 280184A CH 280184D A CH280184D A CH 280184DA CH 280184 A CH280184 A CH 280184A
- Authority
- CH
- Switzerland
- Prior art keywords
- parts
- brown
- dye
- oxybenzene
- amino
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title description 2
- 239000000975 dye Substances 0.000 claims description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 7
- 230000008878 coupling Effects 0.000 claims description 6
- 238000010168 coupling process Methods 0.000 claims description 6
- 238000005859 coupling reaction Methods 0.000 claims description 6
- 150000008049 diazo compounds Chemical class 0.000 claims description 4
- 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 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- 229920000742 Cotton Polymers 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
- 239000000987 azo dye Substances 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000007747 plating Methods 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/38—Trisazo dyes ot the type
- C09B35/40—Trisazo dyes ot the type the component K being a dihydroxy or polyhydroxy compound
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines Trisazofarbstoffes. Es wurde gefunden, dass man zu einem wertvollen Trisazofarbstoff gelangt, wenn man 1,3=Dioxvbenzol einerseits mit diazotier- tem 2-Amino-1.-oxvbenzol-4-sulfonsäureamid und anderseits mit einer Diazov erbindung des Monoazofarbstoffes der Formel
EMI0001.0010
kuppelt.
Der neue Farbstoff bildet ein dunkles Pulver, das sich in Wasser und verdünnter Natriumcarbonatlösung mit brauner, in ver dünnter Natriumhy droxydlösung mit rotbrau ner und in konzentrierter Schwefelsäure mit roter Farbe löst. Fr färbt Baumwolle nach dem ein- oder zweibadigen Nachkupferungs- verfahren in braunen Tönen von guter Licht echtheit und sehr guten Nassechtheiten.
,Die als Ausgangsstoff dienende Diaäover- bindung des lIonoazofarbstoffes der oben an gegebenen Formel kann man herstellen, indem man tetrazotiertes 4-(4'-Aminobenzoylamino)- 1-aminoberizol im molekularen Verhältnis 1 :1. mit 2-Oxybenzol-1.-carboiusäure kuppelt..
Die Kupplung des 1,3-Dioxybenzols mit den beiden Diazoverbindungen kann in belie biger Reihenfolge vorgenommen werden. Es empfiehlt sieh, zuerst die Kupplung mit dem dianotierten 2-Amino-1.-oxybenzol-4-sulfon- säure-aniicl durchzuführen. Die Kupplungen werden mit Vorteil in alkalischem, beispiels weise alkaliearbonatalkalischem. Medium aus geführt.
Beispiel: 18,8 Teile 2-Amino-l-oxybenzol-4-sulfon- säureamid werden unter Zusatz von 25 Teilen 30 o/oiger Salzsäure in 150 Teilen Wasser ge löst. 7Alan dianotiert bei 0 durch Zutropfen einer Lösung von 6,9 Teilen Natriumnitrit in 25 Teilen Wasser, wobei die Diazoverbindung zum Teil ausfällt.
Diese Suspension vereinigt man mit einer Lösung von 11 Teilen 1,3-Di- oxybenzol in 20 Teilen Wasser und lässt zur Kupplung das Gemisch unter Rühren zu 200 Teilen 20 o/oiger Natriumcarbonatlösung von 8 bis 10 fliessen. Nach 5 Stunden Rühren wird. das Reaktionsgemisch mit Salzsäure ange säuert und der Monoazofarbstoff durch Filtra tion abgetrennt.
Das so erhaltene Produkt wird in 400 Tei len Wasser unter Zugabe von 13 Teilen 30 o/oiger Natriumhydroxydlösung gelöst und bei 7.0 einer Diazolösung zugesetzt, die man wie folgt erhält 22,7 Teile 4- (4'-Aminobenzoylamino) -1- am.inobenzol werden unter Zusatz von 50 Vo- lumteilen 30 %iger Salzsäure in 400 Teilen Wasser gelöst.
Durch Zutropfen einer Lösung von 13,8 Teilen Natriumnitrit in 50 Teilen Wasser bei 0 bis 5 erhält man eine klare Tetrazolösung. Nach dem. Einstürzen einer Lö sung aus 14, < i Teilen 1-Oxybenzol-2-carbon- säure und 50 Teilen wasserfreiem Natrium- carbonat in 400 Teilen Wasser zur Tetrazo- lösung rührt man bei 10 bis zur vollständi gen Bildung der Diazoazoverbindinmg.
Nach 24stündigem Rühren erwärmt man das Kupplungsgemisch auf 60 und trennt nach dem Zusatz von Natriumehlorid den Farbstoff durch Filtration ab.
Process for the preparation of a trisazo dye. It has been found that a valuable trisazo dye is obtained if 1,3 = dioxvbenzene is used on the one hand with diazotized 2-amino-1.-oxvbenzene-4-sulfonic acid amide and on the other hand with a diazo compound of the monoazo dye of the formula
EMI0001.0010
clutch.
The new dye forms a dark powder that dissolves in water and dilute sodium carbonate solution with brown, in dilute sodium hydroxide solution with red-brown and in concentrated sulfuric acid with red color. Fr dyes cotton using the one- or two-bath re-coppering process in brown shades of good lightfastness and very good wetfastness.
, The starting material Diaäover- compound of the lionoazo dye of the formula given above can be prepared by tetrazotized 4- (4'-aminobenzoylamino) -1-aminoberizole in a molecular ratio of 1: 1. coupled with 2-oxybenzene-1-carbonic acid ..
The coupling of the 1,3-dioxybenzene with the two diazo compounds can be carried out in any order. It is advisable to first perform the coupling with the dianotated 2-amino-1-oxybenzene-4-sulfonic acid aniicl. The couplings are advantageously in alkaline, for example alkali carbonate alkaline. Medium out.
Example: 18.8 parts of 2-amino-1-oxybenzene-4-sulfonic acid amide are dissolved in 150 parts of water with the addition of 25 parts of 30% hydrochloric acid. 7Alan dianotates at 0 by adding dropwise a solution of 6.9 parts of sodium nitrite in 25 parts of water, some of the diazo compound precipitating out.
This suspension is combined with a solution of 11 parts of 1,3-dioxybenzene in 20 parts of water and, for coupling, the mixture is allowed to flow with stirring to 200 parts of 20% strength sodium carbonate solution of 8 to 10. After stirring for 5 hours. the reaction mixture is acidified with hydrochloric acid and the monoazo dye is separated off by filtration.
The product thus obtained is dissolved in 400 parts of water with the addition of 13 parts of 30% sodium hydroxide solution and added at 7.0 to a diazo solution, which is obtained as follows: 22.7 parts of 4- (4'-aminobenzoylamino) -1- am. inobenzene are dissolved in 400 parts of water with the addition of 50 parts by volume of 30% strength hydrochloric acid.
A clear tetrazo solution is obtained by adding dropwise a solution of 13.8 parts of sodium nitrite in 50 parts of water at 0 to 5. After this. A solution of 14.1 parts of 1-oxybenzene-2-carboxylic acid and 50 parts of anhydrous sodium carbonate in 400 parts of water collapse to give the tetrazo solution, and the mixture is stirred at 10 until the diazoazo compound is completely formed.
After stirring for 24 hours, the coupling mixture is heated to 60 and, after the addition of sodium chloride, the dye is separated off by filtration.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH280184T | 1949-07-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH280184A true CH280184A (en) | 1952-01-15 |
Family
ID=4482579
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH280184D CH280184A (en) | 1949-07-20 | 1949-07-20 | Process for the preparation of a trisazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH280184A (en) |
-
1949
- 1949-07-20 CH CH280184D patent/CH280184A/en unknown
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