CH252274A - Process for the preparation of an azo dye. - Google Patents
Process for the preparation of an azo dye.Info
- Publication number
- CH252274A CH252274A CH252274DA CH252274A CH 252274 A CH252274 A CH 252274A CH 252274D A CH252274D A CH 252274DA CH 252274 A CH252274 A CH 252274A
- Authority
- CH
- Switzerland
- Prior art keywords
- brown
- acid
- oxybenzene
- parts
- chloro
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 239000000987 azo dye Substances 0.000 title claims description 4
- 239000000975 dye Substances 0.000 claims description 7
- 150000001875 compounds Chemical class 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
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 238000004519 manufacturing process 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
- 230000008878 coupling Effects 0.000 description 5
- 238000010168 coupling process Methods 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 239000000243 solution Substances 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
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- 229960004889 salicylic acid Drugs 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[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
- 238000007747 plating Methods 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
<B>Zusatzpatent</B> 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- azotierter 4-Chlor-2-amino-l-oxybenzol-6-sul- f onsäure und anderseits mit der Diazoazover- bindüng aus tetrazotiertem Benzidin und Salicylsäure vereinigt.
Der neue Farbstoff stellt ein dunkles Pulver dar, das sich in Wasser mit rotbrau ner, in verdünnten Alkalien mit brauner, in konz. Schwefelsäure mit violetter Farbe löst und Baumwolle nach dem ein- oder zweibadi- gen 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-Dioxynaphthalin zuerst mit di anotierter 4-Chlor-2-amino-l-oxybenzol-6-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 während einer Stunde bei 5 bis 6 mit einer Lösung von 8 Teilen Salicylsäure und 20 Teilen Natriumcarbonat in 80 Teilen Was ser. Man erhält eine braunorange Suspension der Diazoazoverbsndung.
11,2 Teile 4-Ch"lor-2-amino-l-oxybenzol- 6-sulfonsäure werden in üblicher Weise mit Salzsäure und Natri.umnitrit diazotiert. Die Diazolösung wird innert 1/2 Stunde bei 4 bis 6 in eine Lösung von 8,5 Teilen 1 ,3-Dioxy- naphthalin, 8 Teilen Natriumcarbonat und 2 Teilen Natriumhydroxyd in 50 Teilen Wasser eingetragen.
Man rührt während 1 Stunde bei 5 bis 8 und während 4 Stun den bei. 15 bis 20 . Der Farbstoff wird durch Zusatz von 40 Teilen Natriumchlorid abge schieden und abfiltriert. Er wird in Pasten form in die Suspension der obigen Diazoazo- verbindung eingetragen.
Man kuppelt 1 Stunde bei 10 bis 12 und 50 Stunden bei 18 bis 22 , erwärmt nach dem Verdünnen des Kupp lungsgemisches mit 100 Teilen Wasser .auf 85 , filtriert den gebildeten Trisazofarbstoff aus. dem heissen Reaktionsgemisch ab und trocknet ihn.
<B> Additional patent </B> 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 combined on the one hand with diazoazotized 4-chloro-2-amino-1-oxybenzene-6-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 with redbrau ner, in dilute alkalis with brown, in conc. Sulfuric acid dissolves with a violet color and dyes cotton in real, brown tones using the one or two bath post-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 way that 1,3-dioxynaphthalene is first combined with di-anotized 4-chloro-2-amino-1-oxybenzene-6-sulphonic acid and the resulting monoazo dye is then combined with that of tetrazotized benzidine and Sali in a known manner - Cylic acid is coupled diazoazo compound obtained by coupling on one side.
<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 salicylic acid and 20 parts of sodium carbonate in 80 parts of water. A brown-orange suspension of the diazoazo compound is obtained.
11.2 parts of 4-chloro-2-amino-1-oxybenzene-6-sulfonic acid are diazotized in the usual way with hydrochloric acid and sodium nitrite. The diazo solution is converted into a solution of 8 within 1/2 hour at 4 to 6 , 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 for 1 hour at 5 to 8 and for 4 hours with. 15 to 20. The dye is separated out by the addition of 40 parts of sodium chloride and filtered off. It is added in paste form to the suspension of the above diazoazo compound.
Coupling is carried out for 1 hour at 10 to 12 and 50 hours at 18 to 22, heated after dilution of the coupling mixture with 100 parts of water to 85, and the trisazo dye formed is filtered out. the hot reaction mixture and dries it.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH252274T | 1942-09-02 | ||
| CH246672T | 1943-07-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH252274A true CH252274A (en) | 1947-12-15 |
Family
ID=25729127
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH252274D CH252274A (en) | 1942-09-02 | 1942-09-02 | Process for the preparation of an azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH252274A (en) |
-
1942
- 1942-09-02 CH CH252274D patent/CH252274A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH252274A (en) | Process for the preparation of an azo dye. | |
| CH252280A (en) | Process for the preparation of an azo dye. | |
| AT166464B (en) | Process for the production of new polyazo dyes | |
| CH232507A (en) | Process for the preparation of a disazo dye. | |
| CH252282A (en) | Process for the preparation of an azo dye. | |
| CH252278A (en) | Process for the preparation of an azo dye. | |
| CH252277A (en) | Process for the preparation of an azo dye. | |
| CH232510A (en) | Process for the preparation of a disazo dye. | |
| CH252275A (en) | Process for the preparation of an azo dye. | |
| CH246672A (en) | Process for the preparation of an azo dye. | |
| CH252279A (en) | Process for the preparation of an azo dye. | |
| CH239329A (en) | Process for the preparation of a disazo dye. | |
| CH239338A (en) | Process for the preparation of an azo dye. | |
| CH252281A (en) | Process for the preparation of an azo dye. | |
| CH252276A (en) | Process for the preparation of an azo dye. | |
| CH239339A (en) | Process for the preparation of an azo dye. | |
| CH239325A (en) | Process for the preparation of a disazo dye. | |
| CH239331A (en) | Process for the preparation of a disazo dye. | |
| CH239324A (en) | Process for the preparation of a disazo dye. | |
| CH239330A (en) | Process for the preparation of a disazo dye. | |
| CH239327A (en) | Process for the preparation of a disazo dye. | |
| CH261058A (en) | Process for the preparation of a polyazo dye. | |
| CH211012A (en) | Process for the preparation of a trisazo dye. | |
| CH239322A (en) | Process for the preparation of a disazo dye. | |
| CH239341A (en) | Process for the preparation of an azo dye. |