CH183453A - Process for the preparation of an azo dye. - Google Patents
Process for the preparation of an azo dye.Info
- Publication number
- CH183453A CH183453A CH183453DA CH183453A CH 183453 A CH183453 A CH 183453A CH 183453D A CH183453D A CH 183453DA CH 183453 A CH183453 A CH 183453A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- azo dye
- parts
- preparation
- azo
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 2
- 239000000975 dye Substances 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- -1 triazole compound 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
- 229920000742 Cotton Polymers 0.000 claims description 2
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 2
- 125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- GHBWBMDGBCKAQU-UHFFFAOYSA-N 5-amino-2-[2-(4-nitro-2-sulfophenyl)ethenyl]benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC(N)=CC=C1C=CC1=CC=C([N+]([O-])=O)C=C1S(O)(=O)=O GHBWBMDGBCKAQU-UHFFFAOYSA-N 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- SEMRCUIXRUXGJX-UHFFFAOYSA-N 6-aminonaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=CC2=CC(N)=CC=C21 SEMRCUIXRUXGJX-UHFFFAOYSA-N 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
Description
Verfahren zur Herstellung eines Azofarbstoffes. Vorliegendes Patent bezieht sich auf ein Verfahren zur Herstellung eines Azofarb- stoffes, dadurch gekennzeichnet, dass man den o-Aminoazofarbatoff aus diazotierter 4-Nitro- 4' - aminostilben - 2 . 2' - disulfosäure und der 2-Amit)onaphthalin-6-sulfosäure mit Trauben zucker reduziert und das Reduktionsprodukt zur Triazolverbindung oxydiert.
Das so erhaltene Gemisch von Farbstof fen der Formel: worin für den einen Farbstoff g die Azo- gruppe und für den andern die Azoxygruppe bedeutet, löst sich in Wasser mit gelber, in konzentrierter Schwefelsäure mit rotvioletter Farbe und färbt Baumwolle in lichtechten, gelben Tönen.
<I>Beispiel:</I> Die Diazoverbiudung von 42,2 Teilen 4-Nitro-4'-aminostilben-2. 2'-disulfosäurewird in üblicher Weise mit 25 Teilen 2-Amino- naphthalin-6-sulfosäure gekuppelt. Die abge- scbiedene Farbstoffpaste löst man in 1200 Teilen Wasser und 76 Teilen Natronlauge von 36 B6. Man gibt 11 Teile Trauben zucker hinzu und reduziert während 3 Stun den bei 75 C.
Durch Neutralisieren mit Salzsäure wird das Reduktionsprodukt abge schieden, in 1200 Teilen Wasser gelöst, mit
EMI0001.0027
1$* Teilen Soda versetzt und bei Siedetem peratur mit einer wässerigen Lösung von 52 Teilen kristallisiertem Kupfersulfat oxy diert. Man filtriert von ausgefallenem Kupfer oxydul und scheidet aus dem Filtrat durch Zusatz von 10 % Salz die Triazolverbin- dung ab.
Process for the preparation of an azo dye. The present patent relates to a process for the production of an azo dye, characterized in that the o-aminoazo carbate is obtained from diazotized 4-nitro-4'-aminostilbene-2. 2 '- disulfonic acid and the 2-amit) onaphthalene-6-sulfonic acid reduced with grape sugar and the reduction product is oxidized to the triazole compound.
The resulting mixture of dyes of the formula: in which for one dye g the azo group and for the other the azoxy group, dissolves in water with a yellow color, in concentrated sulfuric acid with red-violet color and dyes cotton in lightfast, yellow tones.
<I> Example: </I> The diazo compound of 42.2 parts of 4-nitro-4'-aminostilbene-2. 2'-disulfonic acid is coupled in the usual way with 25 parts of 2-amino-naphthalene-6-sulfonic acid. The separated dye paste is dissolved in 1200 parts of water and 76 parts of 36 B6 sodium hydroxide solution. 11 parts of grape sugar are added and reduced for 3 hours at 75 C.
By neutralizing with hydrochloric acid, the reduction product is separated out, dissolved in 1200 parts of water, with
EMI0001.0027
1 $ * parts of soda are added and the mixture is oxidized at boiling temperature with an aqueous solution of 52 parts of crystallized copper sulfate. The precipitated copper oxide is filtered off and the triazole compound is separated from the filtrate by adding 10% salt.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE183453X | 1933-07-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH183453A true CH183453A (en) | 1936-04-15 |
Family
ID=5718571
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH183453D CH183453A (en) | 1933-07-25 | 1934-07-19 | Process for the preparation of an azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH183453A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2795577A (en) * | 1956-07-06 | 1957-06-11 | Althouse Chemical Co | Disazo compounds |
-
1934
- 1934-07-19 CH CH183453D patent/CH183453A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2795577A (en) * | 1956-07-06 | 1957-06-11 | Althouse Chemical Co | Disazo compounds |
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