CH252277A - Process for the preparation of an azo dye. - Google Patents
Process for the preparation of an azo dye.Info
- Publication number
- CH252277A CH252277A CH252277DA CH252277A CH 252277 A CH252277 A CH 252277A CH 252277D A CH252277D A CH 252277DA CH 252277 A CH252277 A CH 252277A
- Authority
- CH
- Switzerland
- Prior art keywords
- brown
- acid
- amino
- ogybenzene
- diogynaphthalene
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 239000000975 dye Substances 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
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 2
- 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
- 239000003086 colorant Substances 0.000 claims 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 6
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 3
- 150000008049 diazo compounds Chemical class 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
- 229960004889 salicylic acid Drugs 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
- 239000000725 suspension Substances 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-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
<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-Diogynaplhthalin einerseits mit di- azotierter 2 - Amino -1- ogybenzol - 6 - carbon- säure-4-sulfonsäure und anderseits mit der Diazoazoverbindung aus tetrazotiertem Benz idin und Salicylsäure vereinigt.
Der neue Farbstoff stellt ein dunkles Pulver dar, das sich in Wasser mit orange brauner, in. verdünnter Natriumcarbonat- lösung mit gelbbrauner, in verdünnten Atz- alkalien mit braunroter und in konz. Schwe felsäure mit violetter Farbe löst und Baum wolle nach dem ein- oder zweibadigen Nach- kupferungsverfaliren in echten, braunen Tö nen färbt.
Die Kupplung des 1,3-Diogynaphthalins 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 2 - Amino -1- ogybenzol - 6 - carbon- säure-4-sulfonsäure vereinigt und der ent standene Monoazofarbstoff hierauf mit der in bekannter Weise aus tetrazotiertem Benz- idin und Salicylsäure durch einseitige Kupplung erhaltenen 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 Diazoazoverbindung.
11,6 Teile 2-Amino-l-phenol-6-carbon- säure-4-sulfonsäure werden in üblicherweise mit Salzsäure und Natriumnitrit dianotiert.
Die Diazoverbindung wird innert 1/2 Stunde bei 4 bis 6 in eine Lösung von 8,5 Teilen 1,3 Diogynaphthalin, 8 Teilen Natriumcarbo- nat und 2 Teilen Natriumhydrogyd in 50 Teilen Wasser enngetragen. Man rührt eine Stunde bei 5 bis 8 und 14 Stunden bei 10 bis. 15 .
Der Farbstoff wird durch Zusatz von 60 Teilen Natriumchlorid abgeschieden und abfiltriert. Er 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 , er wärmt nach dem Verdünnen des Kupplungs gemisches mit 100 Teilen Wasser bei 85 ,
fil- tT'iert den gebildeten TTisazofarbstoff aus dem heissen Reaktionsgemisch ab und trock net 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-Diogynaplhthalin combined on the one hand with diazoazotized 2-amino-1-ogybenzene-6-carboxylic acid-4-sulfonic 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 orange-brown, in. Dilute sodium carbonate solution with yellow-brown, in dilute caustic alkalis with brown-red and in conc. Sulfuric acid dissolves with a violet color and, after one or two baths of copper plating, stains cotton in real, brown tones.
The coupling of 1,3-diogynaphthalene 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 kind that 1,3-Diogynaphthalin first combined with di anotized 2 - amino -1- ogybenzene - 6 - carboxylic acid-4-sulfonic acid and the resulting monoazo dye then with the in a known manner from tetrazotized benzidine and Salicylic acid is coupled diazoazo compound obtained by one-sided coupling.
<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.
11.6 parts of 2-amino-1-phenol-6-carboxylic acid-4-sulfonic acid are usually dianotized with hydrochloric acid and sodium nitrite.
The diazo compound is carried over half an 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 for one hour at 5 to 8 and 14 hours at 10 to. 15th
The dye is precipitated by adding 60 parts of sodium chloride and filtered off. It is added in paste form to the suspension of the above diazoazo compound. You couple one hour at 10 to 12 and 50 hours at 18 to 22, he warms after diluting the coupling mixture with 100 parts of water at 85,
The TTisazo 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 |
|---|---|---|---|
| CH252277T | 1942-09-02 | ||
| CH246672T | 1943-07-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH252277A true CH252277A (en) | 1947-12-15 |
Family
ID=25729130
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH252277D CH252277A (en) | 1942-09-02 | 1942-09-02 | Process for the preparation of an azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH252277A (en) |
-
1942
- 1942-09-02 CH CH252277D patent/CH252277A/en unknown
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