AT54264B - Process for the preparation of alizarin red vat dyes. - Google Patents
Process for the preparation of alizarin red vat dyes.Info
- Publication number
- AT54264B AT54264B AT54264DA AT54264B AT 54264 B AT54264 B AT 54264B AT 54264D A AT54264D A AT 54264DA AT 54264 B AT54264 B AT 54264B
- Authority
- AT
- Austria
- Prior art keywords
- preparation
- alizarin red
- vat dyes
- red vat
- red
- Prior art date
Links
- RGCKGOZRHPZPFP-UHFFFAOYSA-N alizarin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 title claims description 4
- 239000000984 vat dye Substances 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- 238000004040 coloring Methods 0.000 claims 1
- 239000000975 dye Substances 0.000 description 4
- -1 Anthraquinone acridones Chemical class 0.000 description 3
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 3
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 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 description 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- GDALETGZDYOOGB-UHFFFAOYSA-N Acridone Natural products C1=C(O)C=C2N(C)C3=CC=CC=C3C(=O)C2=C1O GDALETGZDYOOGB-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-N dithionous acid Chemical compound OS(=O)S(O)=O GRWZHXKQBITJKP-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Darstellung von alizarinroten Küpenfarbstoffen.
Neuerdings sind Anthrachinonakridone als Küpenfarbstoffe erkannt worden und es wurde nun gefunden, dass unter den bisher unbekannten Anthrachinonakridonen, welche im Henzolkerja substituiert sind, diejenigen mit Halogen in Parastellung zum Karbonyl, also die Verbindungen der Konstitution :
EMI1.1
ganz besonders wertvolle Produkte sind. Während das einfache Anthrachinonakridon trübe blaurote Färbungen liefert, sind überraschenderweise diejenigen, welche man mit den Bz-para-halogensubstituierten l-Anthrachinonakridonen erhält, von der Nuance sowie Echtheit des Alizarinrots.
Die neuen Farbstoffe gewinnt man durch Einwirkung von wasserentziehenden Mitteln
EMI1.2
werden bei in 2UO Teile Chlorsulfonsäure eingetragen und Stunde bei jener Temperatur gerührt. Beim Eingiessen der Reaktionamasse in Eiswasser scheidet sich der Farbstoff ab.
Er ist em gelbrotes Pulver, das sich in den gebräuchlichen Lösungsmitteln schwer oder gar nicht löst ; aus Nitrobenzol kann es nmkristaUisiert werden. Mit alkalischem Hydrosulfit gibt der Farbstoff eine rotviolette Küpe, welche Baumwolle anfärbt und beim Ver- hangen an der Luft eine gelbstichig rote Färbung in der Nuance des Türkischrot von ausgezeichneter Echtheit gibt.
In analoger Weise wird beispielsweise das gleichkonstituierte Anthrachinonbromakridon mit sehr ähnlichen Eigenschaften gewonnen.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for the preparation of alizarin red vat dyes.
Anthraquinone acridones have recently been recognized as vat dyes and it has now been found that among the previously unknown anthraquinone acridones which are substituted in Henzolkerja, those with halogen in the para position to the carbonyl, i.e. the compounds of the constitution:
EMI1.1
are particularly valuable products. While the simple anthraquinone acridone provides cloudy bluish-red colorations, surprisingly those obtained with the Bz-para-halogen-substituted l-anthraquinone acridones have the nuance and authenticity of the alizarin red.
The new dyes are obtained through the action of dehydrating agents
EMI1.2
are entered in 2UO parts of chlorosulfonic acid and stirred for one hour at that temperature. When the reaction mixture is poured into ice water, the dye separates out.
It is a yellow-red powder that dissolves with difficulty or not at all in common solvents; it can be crystallized from nitrobenzene. With alkaline hydrosulphite, the dye gives a red-violet vat, which dyes cotton and, when hung in the air, gives it a yellowish red color in the shade of Turkish red of excellent fastness.
In an analogous manner, for example, the identically constituted anthraquinone bromoacridone with very similar properties is obtained.
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE54264X | 1910-01-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT54264B true AT54264B (en) | 1912-07-10 |
Family
ID=5627958
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT54264D AT54264B (en) | 1910-01-26 | 1910-10-21 | Process for the preparation of alizarin red vat dyes. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT54264B (en) |
-
1910
- 1910-10-21 AT AT54264D patent/AT54264B/en active
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