CH302027A - Process for the preparation of a trisazo dye. - Google Patents
Process for the preparation of a trisazo dye.Info
- Publication number
- CH302027A CH302027A CH302027DA CH302027A CH 302027 A CH302027 A CH 302027A CH 302027D A CH302027D A CH 302027DA CH 302027 A CH302027 A CH 302027A
- 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 11
- 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
- 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 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
- SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-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
- 239000000987 azo dye Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 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
- 239000000203 mixture Substances 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
Zusatzpatent 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-(4"-Aminoben- zoylamino)
- 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.
Beispiel: 50 Teile 4-(4"-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- m ethoxy- 4'- oxy - 3'- carboxy -1,
1'-azobenzol-5'- sulfonsäure mit 4-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 Natriumace- tat 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.
Additional patent 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 mono azo dye is treated with copper-donating agents and the complex copper compound obtained is diazotized 4- (4 "-aminobenzoylamino)
- 2-methyl-5-methoxy-4'-oxy-3'-carbo-oxy-1,1'-azobenzene-5'-sulfonic acid couples.
The new dye forms a dark powder that dissolves in water with a yellow-brown color. and dyes cotton in yellow-brown tones.
Example: 50 parts of 4- (4 "-Aminobenzoylamino) -2-methyl - 5 - methoxy-4'-oxy-3'-carboxy-1,1'-azobenzene-5'-sulfonic acid, which is commonly used Way by condensation of 4-amino-2-methyl-5- m ethoxy- 4'- oxy - 3'-carboxy -1,
1'-azobenzene-5'-sulfonic acid was obtained with 4-nitrobenzoyl chloride and reduction of the nitro group to the amino group, are suspended as the sodium salt in 1000 parts of water, 7 parts of sodium nitrite are added and ice is added 10 chilled. 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 mixed with 15 parts of crystallized sodium acetate. At 60 to 70, 27 parts of crystallized copper sulfate dissolved in 100 parts of water are added. After a while 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 | ||
| CH302027T | 1950-10-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH302027A true CH302027A (en) | 1954-09-30 |
Family
ID=25733683
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH302027D CH302027A (en) | 1950-10-11 | 1950-10-11 | Process for the preparation of a trisazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH302027A (en) |
-
1950
- 1950-10-11 CH CH302027D patent/CH302027A/en unknown
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