AT57616B - Process for the preparation of vat dyes of the anthracene series. - Google Patents
Process for the preparation of vat dyes of the anthracene series.Info
- Publication number
- AT57616B AT57616B AT57616DA AT57616B AT 57616 B AT57616 B AT 57616B AT 57616D A AT57616D A AT 57616DA AT 57616 B AT57616 B AT 57616B
- Authority
- AT
- Austria
- Prior art keywords
- preparation
- vat dyes
- parts
- anthracene series
- anthracene
- Prior art date
Links
- 239000000984 vat dye Substances 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- 150000001454 anthracenes Chemical class 0.000 title description 3
- 239000000987 azo dye Substances 0.000 claims description 5
- 239000007800 oxidant agent Substances 0.000 claims description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- XOGPDSATLSAZEK-UHFFFAOYSA-N 2-Aminoanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(N)=CC=C3C(=O)C2=C1 XOGPDSATLSAZEK-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 238000002791 soaking Methods 0.000 description 2
- JHWIEAWILPSRMU-UHFFFAOYSA-N 2-methyl-3-pyrimidin-4-ylpropanoic acid Chemical compound OC(=O)C(C)CC1=CC=NC=N1 JHWIEAWILPSRMU-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 125000005577 anthracene group Chemical group 0.000 description 1
- UXOSWMZHKZFJHD-UHFFFAOYSA-N anthracene-2,6-diamine Chemical compound C1=C(N)C=CC2=CC3=CC(N)=CC=C3C=C21 UXOSWMZHKZFJHD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Darstellung von Küpenfarbstoffen der anthrazenreihe.
Es wurde gefunden, dass man zn Küpenfarbstoffen der Anthrazenreihe. gelangt, wenn man die Azofarbstoffe, welche durch Kombination von ss-Diazoanthrachinon und seinen Derivaten mit ss-Aminonanthrazen und seinen Derivaten entstehen, mit oxydierenden Mitteln behandelt. Dabei wird der o-Aminoazofarbstoff zum Pseudoazimidkörper und gleich- zoitig der Anthrazenrest zum Anthrachinon oxydiert.
Dem einfachsten Repräsentanten der neuen Farbstoffe kommt demnach die folgende Formel zu :
EMI1.1
Beispiel 1.
Die Diazoverbindung aus 23 Teilen ss-Aminoanthrachinon wird mit 20 Teilen ss-Anthramin in salzsaurer Lösung gekuppelt und der ausgeschiedene dunkelblaue Azofarbstoff abfiltriert, ausgewaschen und getrocknet.
100 Teile des so erhaltenen Azofarbstoffes werden in r) 00 Teilen Nitrobenzol gelöst und bei 100 bis 1200 allmählich eine Lösung von 150 Teilen Natriumbichromat in 500 Teilen Eisessig zugegeben. Das Oxydationsprodukt scheidet sich beim Erkalten in dunkelgelben Kristalon aus, welche abfiltriert und mit Alkohol gewaschen werden. Der Farbe stoff gibt mit alkalischer Hydrosuintlösung eine violettblaue Küpe, aus welcher Baumwolle in schwarzbrauner Nuance angefärbt wird, die beim Verhängen und Seifen in ein Gelb von hervorragenden Echtheitseigenschaften übergeht.
Beispiel II.
Der aus der Diazoverbindung aus 45 Teilen ss-Aminoanthrachinon und 21 Teilen 2.6-Diaminoanthrazen erhaltene, schwärzliche Flocken bildende AzofarbstoS wird unter Zusatz von etwas Natronlauge in Wasser aufgeschlämmt und bei 100 solange mit Natriumhypochloritlösung versetzt, bis die schwarze Farbe in rötlichgelb übergegangen ist. Das entstandene Oxydationsprodukt wird abfiltriert, ausgewaschen nnd als Paste zum Färben verwendet. Aus seiner violettbraunen Küpe wird Baumwolle in braunschwarzen Tönen angefärbt, die beim Verhängen und Seifen in ein rotstichiges, sehr echtes Gelb übergehen.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for the preparation of vat dyes of the anthracene series.
It has been found that vat dyes of the anthracene series can be used. when the azo dyes, which are formed by combining ß-diazoanthraquinone and its derivatives with ß-aminonanthracene and its derivatives, are treated with oxidizing agents. The o-aminoazo dye is oxidized to the pseudoazimide body and at the same time the anthracene residue is oxidized to the anthraquinone.
The simplest representative of the new dyes therefore has the following formula:
EMI1.1
Example 1.
The diazo compound of 23 parts of β-aminoanthraquinone is coupled with 20 parts of β-anthramine in hydrochloric acid solution and the dark blue azo dye which has separated out is filtered off, washed out and dried.
100 parts of the azo dye thus obtained are dissolved in 100 parts of nitrobenzene and, at 100 to 1200, a solution of 150 parts of sodium dichromate in 500 parts of glacial acetic acid is gradually added. The oxidation product separates out on cooling in dark yellow crystals, which are filtered off and washed with alcohol. The dye gives a violet-blue vat with alkaline hydrosuint solution, from which cotton is dyed in a black-brown shade, which turns into a yellow with excellent fastness properties when hanging and soaking.
Example II.
The blackish flake-forming azo color obtained from the diazo compound from 45 parts of β-aminoanthraquinone and 21 parts of 2,6-diaminoanthracene is suspended in water with the addition of a little sodium hydroxide solution and sodium hypochlorite solution is added at 100 until the black color has turned reddish yellow. The resulting oxidation product is filtered off, washed out and used as a paste for dyeing. From its purple-brown vat, cotton is dyed in brown-black tones, which turn into a reddish, very real yellow when hanging and soaking.
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE57616X | 1911-07-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT57616B true AT57616B (en) | 1913-02-10 |
Family
ID=5629232
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT57616D AT57616B (en) | 1911-07-03 | 1912-05-04 | Process for the preparation of vat dyes of the anthracene series. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT57616B (en) |
-
1912
- 1912-05-04 AT AT57616D patent/AT57616B/en active
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