CH150802A - Process for the production of a vat dye of the anthraquinone acridone series. - Google Patents
Process for the production of a vat dye of the anthraquinone acridone series.Info
- Publication number
- CH150802A CH150802A CH150802DA CH150802A CH 150802 A CH150802 A CH 150802A CH 150802D A CH150802D A CH 150802DA CH 150802 A CH150802 A CH 150802A
- Authority
- CH
- Switzerland
- Prior art keywords
- anthraquinone
- vat dye
- production
- series
- dyed
- Prior art date
Links
- 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 title claims description 5
- 238000000034 method Methods 0.000 title claims description 5
- 239000000984 vat dye Substances 0.000 title claims description 4
- -1 anthraquinone acridone series Chemical class 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 12
- 238000009835 boiling Methods 0.000 claims description 5
- GDALETGZDYOOGB-UHFFFAOYSA-N Acridone Natural products C1=C(O)C=C2N(C)C3=CC=CC=C3C(=O)C2=C1O GDALETGZDYOOGB-UHFFFAOYSA-N 0.000 claims description 4
- FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- DCKYBPULWXTYJB-UHFFFAOYSA-N 1,2,3-trichloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=C(Cl)C(Cl)=C2Cl DCKYBPULWXTYJB-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 150000004056 anthraquinones Chemical class 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- 238000005660 chlorination reaction Methods 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- WITKIIIPSSFHST-UHFFFAOYSA-N 1-[(9,10-dioxoanthracen-1-yl)amino]anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC1=C2C(=O)C3=CC=CC=C3C(=O)C2=CC=C1 WITKIIIPSSFHST-UHFFFAOYSA-N 0.000 description 1
- UQRLKWGPEVNVHT-UHFFFAOYSA-N 3,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC(Cl)=C1 UQRLKWGPEVNVHT-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Coloring (AREA)
Description
Verfahren zur Herstellung eines Küpenfarbstoffes der Anthrachinonala-Idoureihe. Im Hauptpatent ist ein Verfahren zur Herstellung eines Dianthrachinonylamins der Anthrachinonakridonreibe beschrieben, da durch gekennzeichnet, dass man auf Trichlor- anthrachinonakridon, erhältlich durch Chlo rieren von Anthrachinon-l. 2-akridon in Nitro benzol,
1-Benzoylainino-5-aminoatithrachiiion in Gegenwart eines säurebindenden Mittels und eines Katalysators in einem hochsieden den Lösungsmittel einwirken lässt.
Gegenstand vorliegender Erfindung ist nun ein Verfahren zur Herstellung eines Kü- penfarbstoffes der Anthrachinonakridonreihe, dadurch gekennzeichnet, dass man auf Tri- chloranthrachinonakridon, erhältlich durch Chlorieren von Anthrachinon-1.2-akridon in Nitrobenzol, 3.5-Dichloranilin in einem hoch siedenden organischen Lösungsmittel, wie Nitrobenzol, Naphtalin, Dichlorbenzol und andere mehr bei Gegenwart eines säurebin denden Mittels, wie Natriumacetat,
Kalium- carbonat, Natriumcarbonat usw., einwirken lässt. Die Reaktion wird mit Vorteil zwischen ca. <B>1800</B> Lind dem Siedepunkt des Reaktions gemisches durchgeführt.
<I>Beispiel:</I> 20 Teile Trichloranthrachinoriakridon, her gestellt durch Chlorieren von Anthrachinon- 3 <B>1.</B> 2<B>-</B> akridon in Nitrobenzol, und<B>50</B> Teile <B>3.</B> 5-Dichloranilin, <B>5</B> Teile Natriumacetat und <B>50</B> Teile Naphtalin werden während<B>5 - 6</B> Stunden zum Sieden erhitzt. Nach<B>dem Er-</B> kalten wird Solventnaphta zugefügt und<B>fil-</B> triert.
Der Rückstand wird mit verdünnter Salzsäure aufgekocht und mit Wasser bis zur Neutralität ausgewaschen- Das so erhaltene Produkt kristallisiert aus Nitrobenzol in grünen Nadeln, die in den<B>üb-</B> lichen organischen Lösungsmitteln schwer löslich, in konzentrierter Schwefelsäure mit orangeroter Farbe löslich sind. Aus violett gefärbter Hydrosulfitküpe wird Baumwolle in blaustichig grünen Tönen von guten Echt- heitseigenschaften, insbesondere gegen Licht, angefärbt.
Process for the production of a vat dye of the Anthraquinonala Ido series. In the main patent, a process for the preparation of a dianthraquinonylamine of the anthraquinone acridone grater is described, as characterized in that one can rely on trichloro anthraquinone acridone, obtainable by chlorination of anthraquinone-l. 2-akridon in nitro benzene,
1-Benzoylainino-5-aminoatithrachiiion in the presence of an acid-binding agent and a catalyst in a high boiling point allows the solvent to act.
The present invention now relates to a process for producing a vat dye of the anthraquinone acridone series, characterized in that trichloroanthraquinone acridone, obtainable by chlorinating anthraquinone-1,2-acridone in nitrobenzene, 3,5-dichloroaniline in a high-boiling organic solvent such as nitrobenzene is used , Naphthalene, dichlorobenzene and others in the presence of an acid-binding agent such as sodium acetate,
Potassium carbonate, sodium carbonate, etc., can act. The reaction is advantageously carried out between approx. 1800 and the boiling point of the reaction mixture.
<I> Example: </I> 20 parts of trichloroanthraquinoriakridon, produced by chlorinating anthraquinone 3 <B> 1. </B> 2 <B> - </B> akridon in nitrobenzene, and <B> 50 </ B> parts <B> 3. </B> 5-dichloroaniline, <B> 5 </B> parts of sodium acetate and <B> 50 </B> parts of naphthalene are used for <B> 5 - 6 </B> hours heated to boiling. After <B> cooling </B>, solvent naphtha is added and <B> fil- </B> triturated.
The residue is boiled with dilute hydrochloric acid and washed out with water until it is neutral. The product thus obtained crystallizes from nitrobenzene in green needles, which are sparingly soluble in the usual organic solvents, in concentrated sulfuric acid with an orange-red color are soluble. From a violet-colored hydrosulfite vat, cotton is dyed in bluish green tones with good fastness properties, especially against light.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE150802X | 1928-07-04 | ||
| CH143030T | 1929-05-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH150802A true CH150802A (en) | 1931-11-15 |
Family
ID=25714200
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH150802D CH150802A (en) | 1928-07-04 | 1929-07-03 | Process for the production of a vat dye of the anthraquinone acridone series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH150802A (en) |
-
1929
- 1929-07-03 CH CH150802D patent/CH150802A/en unknown
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