CH244510A - Process for the preparation of an azo dye. - Google Patents
Process for the preparation of an azo dye.Info
- Publication number
- CH244510A CH244510A CH244510DA CH244510A CH 244510 A CH244510 A CH 244510A CH 244510D A CH244510D A CH 244510DA CH 244510 A CH244510 A CH 244510A
- Authority
- CH
- Switzerland
- Prior art keywords
- oxy
- dye
- coupling
- pyrazolone
- tetrazotized
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 239000000987 azo dye Substances 0.000 title claims description 4
- 239000000975 dye Substances 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
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 6
- 239000003518 caustics Substances 0.000 claims description 3
- 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 claims description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- -1 monoazo carbate Chemical compound 0.000 claims 1
- 238000007747 plating Methods 0.000 claims 1
- 235000013311 vegetables Nutrition 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 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
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 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. 242160. Verfahren zur Herstellung eines Azofarbstoffes. Es wurde gefunden, dass ein wertvoller Azofarbstoff hergestellt werden kann, wenn man tetrazotiertes 3-Oxy-4,4'-diaminodiphe- nyl einerseits mit dem Monoazofarbstoff,
her gestellt durch Kupplung von 1 Mol diazotier- tem 2-Amino-l-phenol-4-sulfamid mit 1 Mol Resorcin und anderseits mit 1-(4'-Oxy-3'-carb- oxyphenyl)-3-methyl-5-pyrazolon kuppelt.
Der neue Farbstoff ;stellt ein grünbron- zierendes Pulver dar, das, sich in Wasser und verdünnter Sodalösung mit bordeauxroter, in verdünnten Atzalkalien mit braunroter und in konzentrierter Schwefelsäure mit dichroi- tisch rotblauer Farbe löst und vögetabile Fasern nach dem einbadigen Nachkupferungs- verfahren in waschechten, violettbraunen Nuancen färbt.
Die Tetrazotierung des 3-Oxybenzidins kann in bekannter Weise z. B.. in salzsaurer Lösung vorgenommen werden. Die Kupplung der Tetrazoverbindung mit den beiden Azo- komponenten kann in alkalischem, z. B. Al kalihydToxyd oder -carbonat enthaltendem Medium durchgeführt werden und erfolgt zweckmässig in zwei Stufen.
Hierbei kann man vorteilhaft die Tetrazoverbindung in einer 1. Stufe mit dem oben erwähnten Mono- azofarbstoff und in einer 2. Stufe mit dem erwähnten Pyrazolon vereinigen.
<I>Beispiel:</I> 5,0 Teile 3-Oxybenzidin werden in übli cher Weise in Gegenwart von Salzsäure mit Natriumnitrit tetrazotiert. Die klare Lösung der Tetrazoverbindung wird bei 10-15 zu einer sodaalkalischen Lösung von 7,73 Teilen des Farbstoffes,
hergestellt durch sodaalka- lische Kupplung von 1 Mol diazotiertem 2- Amino-l-phenol-4-sulfamid mit 1 Mol Resor- cin, gegeben.
Man rührt während 1 Stunde bei 10-12 und gibt hierauf zum Kupplungs gemisch eine ätzalkalische Lösung von 5,85 Teilen 1-(4'-Oxy-3'-carboxyphenyl)-3-methyl- 5-pyrazolon. Man rührt während 1 Stunde bei 15-18 und führt die Kupplung durch 20-30stündiges Erwärmen auf 35-40 zu Ende. Durch Zusatz von Kochsalz und Salz- säure wird der Trisazofarbstoff abgeschieden und getrocknet.
Additional patent to main patent No. 242160. Process for the production of an azo dye. It has been found that a valuable azo dye can be produced if tetrazotized 3-oxy-4,4'-diaminodiphenyl on the one hand with the monoazo dye,
made by coupling 1 mole of diazotized 2-amino-1-phenol-4-sulfamide with 1 mole of resorcinol and on the other hand with 1- (4'-oxy-3'-carbo-oxyphenyl) -3-methyl-5- pyrazolone couples.
The new dye is a green-bronzing powder that dissolves in water and dilute soda solution with burgundy red, in dilute caustic alkalis with brown-red and in concentrated sulfuric acid with a dichroic red-blue color, and vögetable fibers after the single-bath re-coppering process in real , purple-brown shades.
The tetrazotization of 3-oxybenzidine can be carried out in a known manner, for. B. be made in hydrochloric acid solution. The coupling of the tetrazo compound with the two azo components can be carried out in an alkaline, e.g. B. Al kalihydToxyd or carbonate-containing medium are carried out and is conveniently carried out in two stages.
Here, the tetrazo compound can advantageously be combined in a 1st stage with the above-mentioned monoazo dye and in a 2nd stage with the mentioned pyrazolone.
<I> Example: </I> 5.0 parts of 3-oxybenzidine are tetrazotized with sodium nitrite in the usual way in the presence of hydrochloric acid. The clear solution of the tetrazo compound becomes a soda-alkaline solution of 7.73 parts of the dye at 10-15
produced by the soda-alkaline coupling of 1 mol of diazotized 2-amino-1-phenol-4-sulfamide with 1 mol of resorcinol.
The mixture is stirred for 1 hour at 10-12 and then a caustic solution of 5.85 parts of 1- (4'-oxy-3'-carboxyphenyl) -3-methyl-5-pyrazolone is added to the coupling mixture. The mixture is stirred for 1 hour at 15-18 and the coupling is completed by heating to 35-40 for 20-30 hours. The trisazo dye is separated out and dried by adding sodium chloride and hydrochloric acid.
Claims (1)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH244510T | 1942-09-03 | ||
| CH244514T | 1942-09-03 | ||
| CH242160T | 1946-04-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH244510A true CH244510A (en) | 1946-09-15 |
Family
ID=27177990
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH244510D CH244510A (en) | 1942-09-03 | 1942-09-03 | Process for the preparation of an azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH244510A (en) |
-
1942
- 1942-09-03 CH CH244510D patent/CH244510A/en unknown
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