AT48686B - Process for the preparation of azo dyes that contain a carbazole derivative. - Google Patents
Process for the preparation of azo dyes that contain a carbazole derivative.Info
- Publication number
- AT48686B AT48686B AT48686DA AT48686B AT 48686 B AT48686 B AT 48686B AT 48686D A AT48686D A AT 48686DA AT 48686 B AT48686 B AT 48686B
- Authority
- AT
- Austria
- Prior art keywords
- preparation
- azo dyes
- contain
- acid
- carbazole derivative
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title description 3
- 238000000034 method Methods 0.000 title description 3
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 title 1
- HBZVNWNSRNTWPS-UHFFFAOYSA-N 6-amino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(O)C2=CC(N)=CC=C21 HBZVNWNSRNTWPS-UHFFFAOYSA-N 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 239000012670 alkaline solution Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- 239000002253 acid Substances 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 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- NRZRRZAVMCAKEP-UHFFFAOYSA-N naphthionic acid Chemical compound C1=CC=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 NRZRRZAVMCAKEP-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
Landscapes
- Coloring (AREA)
Description
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Disazofarbstoff aus Naphthionsäure, 1.7-Naphthylaminsulfosäure und der earbazolierten"-Säure besitzt trotz der drei Sulfogruppen noch in ausgeprägtem Masse die Eigenschaften eines Baum- wollfarbstoffes.
Das Verfahren wird an folgenden Beispielen erläutert :
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Die Tetrazoverbindung aus 184 kg Benzidin wird zunächst mit 1 Molekül Salizylsäure in sodaalkalischer Lösung gekuppelt. Nachdem das Zwischenprodukt sich gebildet hat, lässt man in das Reaktionsprodukt eine sodaalkalische Lösung der berechneten Menge diazotierter γ-Säure einlaufen. Der Diazofarbstoff bildet sich leicht ; er scheidet sich aus dt-r Reaktions- mischung ziemlich vollkommen aus und wird in üblicher Weise aufgearbeitete Er färbt Baumwolle in schönen und echten rötlichbraunen Tönen an.
Beispiel 5 :
Lässt man die Tetrazoverbindung aus 1 Molekiil Benzidin in sodaalkalischer Lösung zunächst auf 1 Molekül carbazolierter y-Säure und nach vollendeter Zwischenkörperbildung auf 1 Molekül
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diamin ersetzt und die zweite Kupplung in schwach essigsaurer Lösung vornimmt. Sie färben die Baumwollfaser direkt rötlich bezw. violettbraun; durch Entwicklung mit diazotiertem p-Nitranilin wird der Ton wesentlich nach braun vertieft und die Waschechtheit erhöht. Die beiden anderen oben angeführten Farbstoffe nus p-Aminosalizytsäure bezw. Aminoazobetizol- sulfonsäure werden gleichfalls in normaler Weise durch Kupplung der carbazolierten γ-Säure in sodaalkalischer Lösung erhalten.
PATENT-ANSPRÜCHE : 1. Verfahren zur Darstellung von Azofarbstoffen, darin bestehend, dass man die aus der
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'. \'erfahren zur Darstellung von Azofarbstoffen, darin bestehend, dass man die aus der 2-Amino-8-naphthol-6-Sulfosäure (γ-Säure) durch die Einwirkung von Arylhydrazinen in Gegen-
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Disazo dye made from naphthionic acid, 1,7-naphthylamine sulfonic acid and earbazolated "acid" still has the properties of a cotton dye to a pronounced degree despite the three sulfo groups.
The process is explained using the following examples:
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The tetrazo compound from 184 kg of benzidine is first coupled with 1 molecule of salicylic acid in a soda-alkaline solution. After the intermediate product has formed, a soda-alkaline solution of the calculated amount of diazotized γ-acid is allowed to run into the reaction product. The disazo dye forms easily; it separates out of the reaction mixture quite completely and is worked up in the usual way. It stains cotton in beautiful and genuine reddish-brown shades.
Example 5:
If the tetrazo compound is made from 1 molecule of benzidine in a soda-alkaline solution, initially to 1 molecule of carbazolated γ-acid and, after the formation of the intermediate body, to 1 molecule
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replaces diamine and performs the second coupling in a weakly acetic acid solution. They dye the cotton fiber directly reddish or. purple brown; development with diazotized p-nitroaniline deepens the shade significantly towards brown and increases the wash fastness. The other two dyes listed above nus p-aminosalicytic acid respectively. Aminoazobetizolesulfonic acids are likewise obtained in the normal way by coupling the carbazolated γ-acid in a soda-alkaline solution.
PATENT CLAIMS: 1. Process for the preparation of azo dyes, consisting in the fact that the from the
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'. Learned about the preparation of azo dyes, consisting in the fact that the from 2-amino-8-naphthol-6-sulfonic acid (γ-acid) by the action of arylhydrazines in counter-
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE48686X | 1909-04-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT48686B true AT48686B (en) | 1911-06-26 |
Family
ID=5626067
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT48686D AT48686B (en) | 1909-04-13 | 1910-03-26 | Process for the preparation of azo dyes that contain a carbazole derivative. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT48686B (en) |
-
1910
- 1910-03-26 AT AT48686D patent/AT48686B/en active
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