CH215071A - Process for the preparation of an azo dye. - Google Patents
Process for the preparation of an azo dye.Info
- Publication number
- CH215071A CH215071A CH215071DA CH215071A CH 215071 A CH215071 A CH 215071A CH 215071D A CH215071D A CH 215071DA CH 215071 A CH215071 A CH 215071A
- Authority
- CH
- Switzerland
- Prior art keywords
- azo dye
- oxalic acid
- parts
- dye
- preparation
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 6
- 239000000975 dye Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 4
- MGCGMYPNXAFGFA-UHFFFAOYSA-N 2-amino-5-nitrobenzonitrile Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C#N MGCGMYPNXAFGFA-UHFFFAOYSA-N 0.000 claims description 3
- 150000003901 oxalic acid esters Chemical class 0.000 claims description 3
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 235000006408 oxalic acid Nutrition 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 125000001302 tertiary amino group Chemical group 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 229920002955 Art silk Polymers 0.000 claims 1
- 150000008049 diazo compounds Chemical class 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines Azofarbstoffes. Es wurde gefunden, dass man einen neuen, wertvollen Azofarbstoff erhält, wenn man Dioxäthylamino-3-methylbenzol, die Dia.zo- verbindung des 1-Amino-2-cyan-4-nitroben- zols und Oxalsäure derart aufeinander ein wirken lässt, dass der saure Oxalsäureester der Dioxäthylaminogruppe entsteht und der Diazorest in 4-,
Stellung zur tertiären Amino- gruppe eintritt.
Der so erhaltene Farbstoff bildet ein dunkles Pulver, das sich in Wasser mit rot violetter Farbe löst und das Acetatkunstseide aus wässriger Lösung in demselben Tone färbt.
<I>Beispiel:</I> 171 Teile 1-Amino-2-cyan-4-nitrobenzol werden in 1000 Teilen konzentrierter Schwe felsäure mit 73,5 Teilen 'Natriumnitrit wie üblich diazotiert. Diese klare Lösung gibt man direkt unter Rühren und ständigem Kühlen zu einer wässrigen Lösung des Oxal- säureesters des Dioxäthylamino-3-methylben- zols, die wie folgt bereitet wird:
195 Teile Dioxäthylamino-3-methylbenzol werden mit 190 Teilen wasserfreier Ogalsäure derart in siedendem Toluol behandelt, dass das sich bil dende Wasser während der Reaktion entfernt wird. Durch Ausschütteln der Toluollösung mit einer Lösung von 250 Teilen konzentrier ter, wässriger Ammonia#klösung in 2000 Teilen Wasser wird die zur Farbstoffherstellung ge eignete wässrige Lösung des Ammoniumsalzes des Esters erhalten.
Nachdem die schwefel saure Diazolösung eingetragen ist, neutrali siert man mit 2600 Teilen 30%iger Natrium hydroxydlösung. Der Farbstoff wird abfil- triert und mit kaltem Wasser ausgewaschen.
Process for the preparation of an azo dye. It has been found that a new, valuable azo dye is obtained if dioxäthylamino-3-methylbenzene, the Dia.zo compound of 1-amino-2-cyano-4-nitrobenzene and oxalic acid can act on one another in such a way that the acidic oxalic acid ester of the dioxethylamino group is formed and the diazo radical is
Position to the tertiary amino group.
The dye thus obtained forms a dark powder which dissolves in water with a red-violet color and dyes the acetate rayon in the same shade from aqueous solution.
<I> Example: </I> 171 parts of 1-amino-2-cyano-4-nitrobenzene are diazotized in 1000 parts of concentrated sulfuric acid with 73.5 parts of sodium nitrite as usual. This clear solution is added directly with stirring and constant cooling to an aqueous solution of the oxalic acid ester of dioxäthylamino-3-methylbenzene, which is prepared as follows:
195 parts of dioxäthylamino-3-methylbenzene are treated with 190 parts of anhydrous ogalic acid in boiling toluene in such a way that the water which forms is removed during the reaction. By shaking the toluene solution with a solution of 250 parts of concentrated aqueous ammonia solution in 2000 parts of water, the aqueous solution of the ammonium salt of the ester suitable for dye production is obtained.
After the sulfuric acid diazo solution has been entered, it is neutralized with 2600 parts of 30% sodium hydroxide solution. The dye is filtered off and washed out with cold water.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH213430T | 1939-11-15 | ||
| CH215071T | 1939-11-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH215071A true CH215071A (en) | 1941-05-31 |
Family
ID=25725442
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH215071D CH215071A (en) | 1939-11-15 | 1939-11-15 | Process for the preparation of an azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH215071A (en) |
-
1939
- 1939-11-15 CH CH215071D patent/CH215071A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH215071A (en) | Process for the preparation of an azo dye. | |
| CH215073A (en) | Process for the preparation of an azo dye. | |
| CH215075A (en) | Process for the preparation of an azo dye. | |
| CH215074A (en) | Process for the preparation of an azo dye. | |
| CH215068A (en) | Process for the preparation of an azo dye. | |
| CH215072A (en) | Process for the preparation of an azo dye. | |
| CH232825A (en) | Process for the preparation of an azo dye. | |
| CH215069A (en) | Process for the preparation of an azo dye. | |
| CH213430A (en) | Process for the preparation of an azo dye. | |
| CH220748A (en) | Process for the preparation of a new pyrazolone derivative. | |
| CH237130A (en) | Process for the production of a new azo dye. | |
| CH211819A (en) | Process for the preparation of an azo dye. | |
| CH229358A (en) | Process for the preparation of a trisazo dye. | |
| CH211600A (en) | Process for the preparation of an azo dye. | |
| CH216416A (en) | Process for the production of a new azo dye. | |
| CH211813A (en) | Process for the preparation of an azo dye. | |
| CH211809A (en) | Process for the preparation of an azo dye. | |
| CH215070A (en) | Process for the preparation of an azo dye. | |
| CH180294A (en) | Process for the production of a new dye. | |
| CH220121A (en) | Process for the production of a new azo dye. | |
| CH202744A (en) | Process for the preparation of an azo dye. | |
| CH229356A (en) | Process for the preparation of a trisazo dye. | |
| CH211833A (en) | Process for the preparation of an azo dye. | |
| CH199786A (en) | Process for the preparation of a new, water-soluble monoazo dye. | |
| CH249784A (en) | Process for the preparation of an azo dye. |