CH252278A - Process for the preparation of an azo dye. - Google Patents
Process for the preparation of an azo dye.Info
- Publication number
- CH252278A CH252278A CH252278DA CH252278A CH 252278 A CH252278 A CH 252278A CH 252278D A CH252278D A CH 252278DA CH 252278 A CH252278 A CH 252278A
- Authority
- CH
- Switzerland
- Prior art keywords
- brown
- coupling
- nitro
- amino
- compound
- 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
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 8
- 230000008878 coupling Effects 0.000 claims description 7
- 238000010168 coupling process Methods 0.000 claims description 7
- 238000005859 coupling reaction Methods 0.000 claims description 7
- 239000000975 dye Substances 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 5
- 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
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 4
- 229960004889 salicylic acid Drugs 0.000 claims description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000003518 caustics Substances 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000007747 plating Methods 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 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
- 150000008049 diazo compounds Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Chemical compound C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution 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
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 246672. Verfahren zur Herstellung eines Azofarbstoffes. Es wurde gefunden, dass ein wertvoller Azofarbstoff hergestellt werden kann, wenn man 1,3-Dioxynaphthalin einerseits mit di- azotiertem 5-Nitro-2-amino-l-oxybenzol und anderseits mit der Diazoazoverbindung aus tetrazotiertem Benzidin und Salicylsäure vereinigt.
Der neue Farbstoff stellt ein dunkles Pulver dar, das sich in Wasser und verdünn ter Natriumcarbonatlösung mit rotbrauner, in verdünnten Ätzalkalien mit violettbrauner, in konz. Schwefelsäure mit violetter Farbe löst und Baumwolle nach dem ein- oder zwei- ba.digen Nachkupferungsverfahren in echten, braunen Tönen färbt.
Die Kupplung des 1,3-Dioxynaphthalins 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-Dioxynaplhthalin zuerst mit di- azotiertem 5-Nitro-2-amino-1.-oxybenzol ver einigt und der entstandene Monoazofarbstoff hierauf mit der in bekannter Weise aus tetr- azotiertem Benzidin und Salicylsäure durch einseitige Kupplung erhaltenen Diazoazover- hindung gekuppelt wird.
<I>Beispiel:</I> 9,2 Teile Benzidin werden mit Salzsäure und Natriumnitrit wie üblich tetrazotiert. Man kombiniert die klare Tetrazolö,sung wäh rend einer Stunde bei 5 bis 6 mit einer Lö sung von 8 Teulen Salicylsäure und 20 Teilen Natriumcarbonat in 80 Teilen Wasser. Man erhält eine braunorange Suspension der Di- azoazoverbindung.
7,7 Teile 5-Nitro-2-amino-l-phenol wer den in üblicher Weise mit Salzsäure und Natriumnitrit diazotiert. Die Suspension der Diazoverbindung wird innert @i/2 Stunde bei 4 bis 6 in eine Lösung von 8,5 Teilen 1,3 Dioxynaphthalin, 8 Teilen Natriumcarbonat und 2 Teilen Natriumhydroxyd :in 50 Teilen Wasser eingetragen. Man rührt während einer Stunde bei 5 bis 8 .
Der Farbstoff wird durch Zusatz von 40 Teilen Natriumchlorid abgeschieden. und abfiltriert. Er wird in Pa- etenform in die Suspension der obigen Diazo- azoverbindung eingetragen. Man kuppelt eine Stunde bei 10 bis 12 und 24 Stunden bei 18 bis 22 , erwärmt nach dem Verdünnen mit 100 Teilen Wasser das Kupplungs gemisch auf 95 , filtriert den gebildeten Trisazofarbstoff aus dem heissen Reaktions gemisch ab und trocknet ihn.
Additional patent to main patent No. 246672. Process for the production of an azo dye. It has been found that a valuable azo dye can be produced if 1,3-dioxynaphthalene is combined on the one hand with di-azotized 5-nitro-2-amino-1-oxybenzene 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 red-brown, in dilute caustic alkalis with violet-brown, in conc. Sulfuric acid with a violet color dissolves and dyes cotton in real, brown tones using the one or two-strand copper plating process.
The coupling of the 1,3-dioxynaphthalene with the two diazo compounds is preferably carried out in an alkaline, e.g. 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-Dioxynaplhthalin first united with diacotized 5-nitro-2-amino-1.-oxybenzene ver and the resulting monoazo dye then with the known from tetra-azotized benzidine and salicylic acid by one-sided coupling obtained diazoazo compound is coupled.
<I> Example: </I> 9.2 parts of benzidine are tetrazotized with hydrochloric acid and sodium nitrite as usual. Combine the clear tetrazole solution for one hour at 5 to 6 with a solution of 8 parts of salicylic acid and 20 parts of sodium carbonate in 80 parts of water. A brown-orange suspension of the diazoazo compound is obtained.
7.7 parts of 5-nitro-2-amino-l-phenol who diazotized in the usual way with hydrochloric acid and sodium nitrite. The suspension of the diazo compound is introduced within 1/2 hour at 4 to 6 in a solution of 8.5 parts of 1,3 dioxynaphthalene, 8 parts of sodium carbonate and 2 parts of sodium hydroxide: in 50 parts of water. The mixture is stirred at 5 to 8 for one hour.
The dye is deposited by adding 40 parts of sodium chloride. and filtered off. It is added to the suspension of the above diazo-azo compound in pawn form. Coupling is carried out for one hour at 10 to 12 and 24 hours at 18 to 22, after dilution with 100 parts of water the coupling mixture is heated to 95, the trisazo dye formed is filtered off from the hot reaction mixture and it is dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH252278T | 1942-09-02 | ||
| CH246672T | 1943-07-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH252278A true CH252278A (en) | 1947-12-15 |
Family
ID=25729131
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH252278D CH252278A (en) | 1942-09-02 | 1942-09-02 | Process for the preparation of an azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH252278A (en) |
-
1942
- 1942-09-02 CH CH252278D patent/CH252278A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH252278A (en) | Process for the preparation of an azo dye. | |
| CH252280A (en) | Process for the preparation of an azo dye. | |
| CH252282A (en) | Process for the preparation of an azo dye. | |
| AT166464B (en) | Process for the production of new polyazo dyes | |
| CH252277A (en) | Process for the preparation of an azo dye. | |
| CH252274A (en) | Process for the preparation of an azo dye. | |
| CH246672A (en) | Process for the preparation of an azo dye. | |
| CH252276A (en) | Process for the preparation of an azo dye. | |
| CH252275A (en) | Process for the preparation of an azo dye. | |
| CH252279A (en) | Process for the preparation of an azo dye. | |
| CH239339A (en) | Process for the preparation of an azo dye. | |
| CH215060A (en) | Process for the production of a copper-containing trisazo dye. | |
| CH239338A (en) | Process for the preparation of an azo dye. | |
| CH239329A (en) | Process for the preparation of a disazo dye. | |
| CH239324A (en) | Process for the preparation of a disazo dye. | |
| CH252281A (en) | Process for the preparation of an azo dye. | |
| CH211004A (en) | Process for the preparation of an azo dye. | |
| CH239331A (en) | Process for the preparation of a disazo dye. | |
| CH244515A (en) | Process for the preparation of an azo dye. | |
| CH239327A (en) | Process for the preparation of a disazo dye. | |
| CH235210A (en) | Process for the preparation of a copper-containing disazo dye. | |
| CH310828A (en) | Process for the production of a metallizable polyazo dye. | |
| CH239330A (en) | Process for the preparation of a disazo dye. | |
| CH261058A (en) | Process for the preparation of a polyazo dye. | |
| CH239325A (en) | Process for the preparation of a disazo dye. |