CH239339A - Process for the preparation of an azo dye. - Google Patents
Process for the preparation of an azo dye.Info
- Publication number
- CH239339A CH239339A CH239339DA CH239339A CH 239339 A CH239339 A CH 239339A CH 239339D A CH239339D A CH 239339DA CH 239339 A CH239339 A CH 239339A
- Authority
- CH
- Switzerland
- Prior art keywords
- pyrazolone
- red
- azo dye
- orange
- hand
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 239000000987 azo dye Substances 0.000 title claims description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 8
- 239000000975 dye Substances 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000003518 caustics Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- YLNDNABNWASMFD-UHFFFAOYSA-N 4-[(1,3-dimethylimidazol-1-ium-2-yl)diazenyl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1N=NC1=[N+](C)C=CN1C YLNDNABNWASMFD-UHFFFAOYSA-N 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- AOZOUSZEPXLSLV-UHFFFAOYSA-N 3-ethyl-1,4-dihydropyrazol-5-one Chemical compound CCC1=NNC(=O)C1 AOZOUSZEPXLSLV-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000007747 plating Methods 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 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
- NHLAPJMCARJFOG-UHFFFAOYSA-N 3-methyl-1,4-dihydropyrazol-5-one Chemical compound CC1=NNC(=O)C1 NHLAPJMCARJFOG-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000003513 alkali Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 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
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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
- C09B35/02—Disazo dyes
- C09B35/039—Disazo dyes characterised by the tetrazo component
- C09B35/08—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl
- C09B35/20—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl from two coupling compounds of different types
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines Azofarbstoffes. Es wurde gefunden, dass ein wertvoller Azofarbstoff hergestellt werden kann, wenn man tetrazotiertes 3-Oxy-3'-methoxybenzidin einerseits mit Salicylsäure und anderseits mit 3-Methyl-5-pyrazolon kuppelt.
Der neue Farbstoff ist ein grünschwarz bronzierendes Pulver, das sich in Wasser mit orangebrauner, in verdünnten Ätzalkalien mit orangeroter und in konzentrierter Schwefel säure mit rubinroter Farbe löst und Baum wolle nach dem ein- oder zweibadigen Nach- kupferungsverfahren in waschechten, roten Tönen färbt.
Das für das vorliegende Verfahren be nötigte 3-Oxy-3'-methoxybenzidin kann nach den Angaben des Hauptpatentes hergestellt werden.
Die Tetrazotierung des 3@Oxy-3i'-methoxy- benzidins erfolgt in bekannter Weise. Die Kupplung der Tetrazoverbindung mit den oben genannten Azokomponenten wird zweck mässig in zwei Stufen durchgeführt, derart, da.ss man zuerst nur eine einseitige Kupplung mit Salicylsäure und hierauf die weitere Kupplung mit 3-Methyl-5-pyrazolon bewirkt. Beide Kupplungen werden zweckmässig in alkalischem, zum Beispiel Alkalicarbonat oder Ätzalkali oder beide enthaltendem, Me dium durchgeführt.
<I>Beispiel:</I> 5,75 g 3-Oxy-3'-methoxybenzidin werden in üblicher Weise in Gegenwart von Salz säure mit Natriumnitrit tetrazotiert. Die klare Lösung der T'etrazoverbindung wird bei 5 mit einer Lösung von 3.,5 g Salicylsäure und C g Natriumhydroxyd in 40 cm3 Wasser ver einigt und das Gemisch während i/2 Stunde bei 4-6 gerührt. Nach dieser Zeit ist der Monoazofarbstoff gebildet.
Man gibt nun zum Kupplungsgemisch eine Lösung von 2,45 g 3-Methyl-5-pyrazolon und 2 g Na triumhydroxyd in 50 cm' Wasser. Man rührt das Gemisch während 1 Stunde bei 10-12 und 20 Stunden bei 15-20 . Durch Zusatz von Kochsalz wird der Farbstoff abgeschie den, dann abfiltriert und getrocknet.
Process for the preparation of an azo dye. It has been found that a valuable azo dye can be produced if tetrazotized 3-oxy-3'-methoxybenzidine is coupled on the one hand with salicylic acid and on the other hand with 3-methyl-5-pyrazolone.
The new dye is a greenish-black bronzing powder that dissolves in water with orange-brown, in dilute caustic alkalis with orange-red and in concentrated sulfuric acid with ruby-red color, and cotton after the one- or two-bath re-coppering process is dyed in washfast red tones.
The 3-oxy-3'-methoxybenzidine required for the present process can be prepared according to the information in the main patent.
The tetrazotization of 3 @ oxy-3i'-methoxybenzidine takes place in a known manner. The coupling of the tetrazo compound with the azo components mentioned above is expediently carried out in two stages, in such a way that first only one coupling with salicylic acid and then the further coupling with 3-methyl-5-pyrazolone are effected. Both couplings are expediently carried out in an alkaline medium, for example alkali metal carbonate or caustic alkali or both.
<I> Example: </I> 5.75 g of 3-oxy-3'-methoxybenzidine are tetrazotized with sodium nitrite in the usual manner in the presence of hydrochloric acid. The clear solution of the tetrazo compound is combined at 5 with a solution of 3, 5 g of salicylic acid and C g of sodium hydroxide in 40 cm3 of water and the mixture is stirred at 4-6 for 1/2 hour. After this time the monoazo dye is formed.
A solution of 2.45 g of 3-methyl-5-pyrazolone and 2 g of sodium hydroxide in 50 cm 'of water is then added to the coupling mixture. The mixture is stirred for 1 hour at 10-12 and 20 hours at 15-20. The dye is deposited by adding sodium chloride, then filtered off and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH239339T | 1942-09-02 | ||
| CH237187T | 1942-09-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH239339A true CH239339A (en) | 1945-09-30 |
Family
ID=25728239
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH239339D CH239339A (en) | 1942-09-02 | 1942-09-02 | Process for the preparation of an azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH239339A (en) |
-
1942
- 1942-09-02 CH CH239339D patent/CH239339A/en unknown
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