CH252276A - Process for the preparation of an azo dye. - Google Patents
Process for the preparation of an azo dye.Info
- Publication number
- CH252276A CH252276A CH252276DA CH252276A CH 252276 A CH252276 A CH 252276A CH 252276D A CH252276D A CH 252276DA CH 252276 A CH252276 A CH 252276A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- nitro
- parts
- dissolves
- azo dye
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 239000000987 azo dye Substances 0.000 title claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 6
- 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
- 239000000975 dye Substances 0.000 claims description 6
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 claims description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 3
- 229960004889 salicylic acid Drugs 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000003518 caustics Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 1
- -1 azo carbate Chemical compound 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000007865 diluting 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
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011780 sodium chloride 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
Zusatzpatent zum Hauptpatent Nr. 246672. Verfahren zur Herstellung eines Azofarbatoffes. Es wurde gefunden, dass ein wertvoller Azofarbstoff hergestellt werden kann, wenn. man 1,
3-Dioxynaphthalin einerseits mit di- azotierter 6-Nitro-2-arn.ino-l-ogybenzol-4-sul- fonsäure und anderseits mit der Diazoazo- verbindung aus tetrazotiertem Benzidin und Salicylssäure vereinigt.
Der neue Farbstoff stellt ein dunkles Pulver dar, das sich in Wasser und verdünn ter Natriumcarbonatlösung mit bordeaux roter, in verdünnten Ätzadkalien mit violett brauner, in konz. Schwefelsäure mit blau roter Farbe, löst und Baumwolle nach dem ein- oder zweibadigen Nachkupferungsver- fahren in echten, braunen Tönen färbt.
Die Kupplung des 1,3-Diogynaphthaliw mit den beiden Diazoverbindungen erfolgt vorzugsweise in alkalischem, z. B. Soda oder Natronlauge enthaltendem Medium. Man bringt die beiden Diazoverbindungen zweck mässig nacheinander zur Kupplung, z.
B. der art, dass 1,3-Diogynaphthalin zuerst mit di anotierter 6-Nütro-2-amino-l-ogybenzol-4-sul- fonsäure vereinigt und der entstandene Mono azofarbstoff hierauf mit der in bekannter Weise aus tetrazotiertem Benzidin und Sali- cylsäure durch einseitige Kupplung erhal tenen Diazoazoverbindung gekuppelt wird.
<I>Beispiel:</I> 9,2 Teile Benzidin werden mit Salzsäure und Natriumnitrit wie üblich tetrazotiert. Man kombiniert die klare Tetrazolösung wäh rend einer Stunde bei 5 bis 6 mit einer Lö- sung von 8 Teilen Sakcylsäure und 20 Tei len Natriumearbonat in 80 Teilen .Wasser. Man erhält eine braunorange Suspension der Diazoazoverbindung.
11,7 Teile 6-Nitro-2-amnophenol-4-sulfon- säure werden in üblicher Weise mit Salz säure und Nätriumnitrit bei 10 hie 15 di- azotiert. Die Diazolösung wird innert 1/2 Stunde bei. 4 bis:
6 in. eine Lösung von 8,5 Teilen 1,3-Diogynaphthalin, 8 Teilen Na- triumcarbonat und 2 Teilen Natriumhydrogyd in 50 Teilen Wasser eingetragen. Man rührt während einer Stunde bei 5 bis 8 . Der Farb stoff wird durch Zusatz von 60 Teilen Na txiumchlorid abgeschieden und abfiltriert. Fr wird in Pastenform in die Suspension der obigen Diazoazoverbindung eingetragen.
Man kuppelt eine Stunde bei 10 bis 12 und 50 Stunden bei 18 bis 22 , erwärmt nach dem Verdünnen des Kupplungsgemisches mit 100 Teilen Wasser auf 85 , filtriert den gebilde ten Trisazofarbstoff aus dem heissen Reak- tionsgemisch ab und trocknet ihn.
Additional patent to main patent No. 246672. Process for the production of an azo carbate. It has been found that a valuable azo dye can be made if. man 1,
3-Dioxynaphthalene combined on the one hand with diazo-2-nitro-2-arn.ino-1-ogybenzene-4-sulphonic acid and on the other hand with the diazoazo compound of tetrazotized benzidine and salicylic acid.
The new dye is a dark powder that dissolves in water and dilute sodium carbonate solution with burgundy red, in dilute caustic soda with purple brown, in conc. Sulfuric acid with a blue-red color, dissolves and dyes cotton in real, brown tones using the one- or two-bath re-coppering process.
The coupling of the 1,3-Diogynaphthaliw with the two diazo compounds is preferably carried out in an alkaline, z. B. Soda or sodium hydroxide containing medium. Bring the two diazo compounds conveniently one after the other to the coupling, for.
B. the type that 1,3-Diogynaphthalin first combined with di anotized 6-Nütro-2-amino-l-ogybenzene-4-sulphonic acid and the resulting mono azo dye then with the in a known manner from tetrazotized benzidine and Sali- Cylic acid is coupled by unilateral coupling obtained diazoazo compound.
<I> Example: </I> 9.2 parts of benzidine are tetrazotized with hydrochloric acid and sodium nitrite as usual. Combine the clear tetrazo solution for one hour at 5 to 6 with a solution of 8 parts of saccycic acid and 20 parts of sodium carbonate in 80 parts of water. A brown-orange suspension of the diazoazo compound is obtained.
11.7 parts of 6-nitro-2-amnophenol-4-sulfonic acid are azotized in the usual way with hydrochloric acid and sodium nitrite at 10 hie 15. The diazo solution is within 1/2 hour at. 4 to:
6 in. A solution of 8.5 parts of 1,3-diogynaphthalene, 8 parts of sodium carbonate and 2 parts of sodium hydrogen in 50 parts of water. The mixture is stirred at 5 to 8 for one hour. The dye is deposited by adding 60 parts of sodium chloride and filtered off. Fr is added in paste form to the suspension of the above diazoazo compound.
Coupling is carried out for one hour at 10 to 12 and 50 hours at 18 to 22, after diluting the coupling mixture with 100 parts of water it is heated to 85, the trisazo dye formed is filtered off from the hot reaction mixture and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH252276T | 1942-09-02 | ||
| CH246672T | 1943-07-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH252276A true CH252276A (en) | 1947-12-15 |
Family
ID=25729129
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH252276D CH252276A (en) | 1942-09-02 | 1942-09-02 | Process for the preparation of an azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH252276A (en) |
-
1942
- 1942-09-02 CH CH252276D patent/CH252276A/en unknown
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