CH302028A - Process for the preparation of a trisazo dye. - Google Patents
Process for the preparation of a trisazo dye.Info
- Publication number
- CH302028A CH302028A CH302028DA CH302028A CH 302028 A CH302028 A CH 302028A CH 302028D A CH302028D A CH 302028DA CH 302028 A CH302028 A CH 302028A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- sulfonic acid
- parts
- oxy
- diazotized
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 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 4
- 239000005749 Copper compound Substances 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 150000001880 copper compounds Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- NXTNASSYJUXJDV-UHFFFAOYSA-N 3-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC(C(Cl)=O)=C1 NXTNASSYJUXJDV-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/48—Preparation from other complex metal compounds of azo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
<B>Zusatzpatent</B> zum Hauptpatent Nr. 296341. Verfahren zur Herstellung eines Trisazofarbstoffes. Es wurde gefunden, dass man zu einem wertvollen Trisazofarbstoff gelangt, wenn man 1,3-Dioxybenzol mit diazotierter 2-Amino-l- oxybenzol-4-sulfonsäure vereinigt, den Mono- azofarbstoff mit kupferabgebenden Mitteln be handelt und.
die erhaltene komplexe Kupfer verbindung mit diazotierter 4-(3"-Aminoben- zoylam ino) - 2-methyl-5-methoxy-4'-oxy-3'-carb- oxy-1,1'-azobenzol-5'-sulfonsäure kuppelt.
Der neue Farbstoff bildet ein dunkles Pul ver, das sich in Wasser mit gelbbrauner Farbe löst und Baumwolle in gelbbraunen Tönen färbt.
<I>Beispiel:</I> 50 Teile 4-(3"-Aminobenzoylamino)-2-me- thyl - 5 -methoxy- 4'-oxy-3'-carboxy-1,1'-azoben- zol-5'-sulfonsäure, welche in üblicher Weise durch Kondensation von 4-Amino-2-methyl-5- methoxy - 4' - oxy - 3'- carboxy -1,1'-azobenzol-5'- sulfonsäure mit 3-Nitrobenzoylchlorid und Re duktion der Nitrogruppe zur Aminogruppe erhalten wurde,
werden als Natriumsalz in <B>1000</B> Teilen Wasser suspendiert, mit 7 Teilen Natriumnitrit versetzt und durch Zugabe von Eis auf 10 gekühlt. Alsdann gibt man unter gutem Rühren 50 Teile 30 % ige Salzsäure hinzu und rührt einige Zeit bei 10 bis 15 .
33 Teile des Monoazofarbstoffes aus diazo- tierter 2-Amino-l-oxybenzol-4-sulfonsäure und Resorcin werden in 500 Teilen Wasser gelöst und mit 15 Teilen kristallisiertem Natrium acetat versetzt. Bei 60 bis 70 werden 27 Teile kristallisiertes Kupfersulfat, gelöst in 100 Tei len Wasser, zugeführt. Nach einiger Zeit wird der gekupferte Monoazofarbstoff ausgesalzen und filtriert.
Dieser wird zusammen mit 50 Teilen wasserfreiem Natriumcarbonat in 400 Teilen Wasser gelöst und die Lösung in Sus pension der Diazoverbindung eingestürzt. Nach beendeter Kupplung wird der Farbstoff ausgesalzen, filtriert und getrocknet.
<B> Additional patent </B> to main patent no. 296341. Process for the production of a trisazo dye. It has been found that a valuable trisazo dye is obtained if 1,3-dioxybenzene is combined with diazotized 2-amino-l-oxybenzene-4-sulfonic acid, the monoazo dye is treated with copper-releasing agents and.
the complex copper compound obtained with diazotized 4- (3 "-aminobenzene-5'-sulfonic acid) -2-methyl-5-methoxy-4'-oxy-3'-carbo-oxy-1,1'-azobenzene-5'-sulfonic acid clutch.
The new dye forms a dark powder that dissolves in water with a yellow-brown color and dyes cotton in yellow-brown tones.
<I> Example: </I> 50 parts of 4- (3 "-aminobenzoylamino) -2-methyl-5-methoxy-4'-oxy-3'-carboxy-1,1'-azobenzene-5 '-sulfonic acid, which in the usual way by condensation of 4-amino-2-methyl-5-methoxy - 4' - oxy - 3'-carboxy -1,1'-azobenzene-5'-sulfonic acid with 3-nitrobenzoyl chloride and Re reduction of the nitro group to the amino group was obtained,
are suspended as the sodium salt in 1000 parts of water, 7 parts of sodium nitrite are added and the mixture is cooled to 10 by adding ice. Then 50 parts of 30% hydrochloric acid are added with thorough stirring and the mixture is stirred at 10 to 15 for some time.
33 parts of the monoazo dye from diazo-tated 2-amino-1-oxybenzene-4-sulfonic acid and resorcinol are dissolved in 500 parts of water, and 15 parts of crystallized sodium acetate are added. At 60 to 70, 27 parts of crystallized copper sulfate, dissolved in 100 parts of water, are added. After some time, the coppered monoazo dye is salted out and filtered.
This is dissolved together with 50 parts of anhydrous sodium carbonate in 400 parts of water and the solution collapsed in the suspension of the diazo compound. After coupling has ended, the dye is salted out, filtered and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH296341T | 1950-10-11 | ||
| CH302028T | 1950-10-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH302028A true CH302028A (en) | 1954-09-30 |
Family
ID=25733684
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH302028D CH302028A (en) | 1950-10-11 | 1950-10-11 | Process for the preparation of a trisazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH302028A (en) |
-
1950
- 1950-10-11 CH CH302028D patent/CH302028A/en unknown
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