CH209573A - Process for the preparation of a dye of the anthraquinone series. - Google Patents
Process for the preparation of a dye of the anthraquinone series.Info
- Publication number
- CH209573A CH209573A CH209573DA CH209573A CH 209573 A CH209573 A CH 209573A CH 209573D A CH209573D A CH 209573DA CH 209573 A CH209573 A CH 209573A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- red
- anthraquinone series
- mol
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 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 4
- 150000004056 anthraquinones Chemical class 0.000 title claims description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 8
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 1
- 239000000975 dye Substances 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- -1 for example Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/48—Anthrimides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Zusatzpatent zum Haupeatent Nr. <B>206728.</B> Verfahren zur Herstellung eines Farbstoffes der Anthrachinonreihe. Vorliegende Erfindung betrifft ein Ver fahren zur Herstellung eines neuen Küpen- farbstoffes der Anthrachinonreihe. Das Ver fahren ist dadurch gekennzeichnet, dass man<B>1</B> Mol 1.5-Dibenzoylamitio-B.7-dihalogenanthra- chinon mit 2 Mol 1-Aminoanthrachiiion um setzt.
Die Umsetzung führt man vorteilhaft in Gegenwart eines alkalischen Mittels wie beispielsweise Natriumearbonat, sowie zweck mässig in Gegenwart eines Kupfersalzes und eines hochsiedenden Lösungsmittels wie Nitro- benzol durch.
Der erhaltene Farbstoff stellt ein dunkel rotes Pulver dar, das sich in konzentrierter Schwefelsäure mit grüner Farbe löst. Die Lösungsfarbe schlägt nach kurzer Zeit in Blau um. Der neue Farbstoff färbt aus rot brauner Küpe Baumwolle mit roter Farbe an. Die Färbungen sind vorzüglich chlor- und lichtecht.
<I>Beispiel:</I> <B>15</B> Gewichtsteile 1.5-Dibenzoylamino-3.7- dibromanthrachinon werden mit 20 Gewichts- teilen 1-Aminoanthrachinon, 20 Gewichts teilen Natriumearbonat, <B>0,5</B> Gewichtsteilen Kupferacetat und 200 Gewichtsteilen Nitro benzol 20 Stunden lang unter Rühren zum Sieden erhitzt. Der Farbstoff wird bei<B>500</B> abgesaugt, mit Nitrobenzol und Alkohol ge waschen und mit Wasser ausgekocht. Er stellt ein dunkelrotes Pulver dar, welches sich in konzentrierter Schwefelsäure mit grü ner Farbe löst. Die Lösungsfarbe schlägt nach kurzer Zeit in Blau um. Der Farbstoff, färbt aus rotbrauner Küpe Baumwolle mit roter Farbe an.
Die Färbung ist vorzüglich ohlor- und lichtecht.
Additional patent to the main patent no. <B> 206728. </B> Process for the production of a dye of the anthraquinone series. The present invention relates to a process for the production of a new vat dye of the anthraquinone series. The process is characterized in that 1 mol of 1,5-dibenzoylamitio-B.7-dihaloanthraquinone is reacted with 2 mol of 1-aminoanthraquinone.
The reaction is advantageously carried out in the presence of an alkaline agent such as, for example, sodium carbonate, and expediently in the presence of a copper salt and a high-boiling solvent such as nitrobenzene.
The dye obtained is a dark red powder that dissolves in concentrated sulfuric acid with a green color. The solution color changes to blue after a short time. The new dye stains cotton from a red-brown vat with a red color. The dyeings are excellent chlorine and lightfast.
<I> Example: </I> <B> 15 </B> parts by weight of 1,5-dibenzoylamino-3.7-dibromoanthraquinone become 20 parts by weight of 1-aminoanthraquinone, 20 parts by weight of sodium carbonate, <B> 0.5 </B> Parts by weight of copper acetate and 200 parts by weight of nitro benzene heated to boiling for 20 hours with stirring. The dye is sucked off at <B> 500 </B>, washed with nitrobenzene and alcohol and boiled with water. It is a dark red powder that dissolves in concentrated sulfuric acid with a green color. The solution color changes to blue after a short time. The dye, from the red-brown vat, stains cotton with red color.
The coloration is extremely resistant to chlorine and light.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE209573X | 1937-06-25 | ||
| CH206728T | 1938-06-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH209573A true CH209573A (en) | 1940-04-15 |
Family
ID=25724347
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH209573D CH209573A (en) | 1937-06-25 | 1938-06-21 | Process for the preparation of a dye of the anthraquinone series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH209573A (en) |
-
1938
- 1938-06-21 CH CH209573D patent/CH209573A/en unknown
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