CH184187A - 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
- CH184187A CH184187A CH184187DA CH184187A CH 184187 A CH184187 A CH 184187A CH 184187D A CH184187D A CH 184187DA CH 184187 A CH184187 A CH 184187A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- anthraquinone
- preparation
- anthraquinone series
- methyl ester
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 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 3
- 150000004056 anthraquinones Chemical class 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 2
- 239000000975 dye Substances 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 2
- -1 1,4-di-p-toluidino-anthraquinone-6-carboxylic acid methyl ester Chemical compound 0.000 description 1
- GJCXEZRZCYGZMW-UHFFFAOYSA-N COC(C(C=C1C(C2=C3C(Cl)=CC=C2Cl)=O)=CC=C1C3=O)=O Chemical compound COC(C(C=C1C(C2=C3C(Cl)=CC=C2Cl)=O)=CC=C1C3=O)=O GJCXEZRZCYGZMW-UHFFFAOYSA-N 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 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
- 238000010438 heat treatment Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Farbstoffes der Anthracliinonreihe. Das Hauptpatent betrifft- ein Verfahren zur Herstellung eines Farbstoffes der An- tlirachinonreihe, bei dem der 1 . 4-Di-p-tolui- dinoanthrachinon - 2) - carbonsäuremethylester so lange mit einem sulfonierend wirkenden Mittel behandelt wird, bis eine aufgearbei tete Probe völlig wasserlöslich geworden ist.
Es wurde nun gefunden, dass man einen ähnlich wertvollen Farbstoff der Anthrachi- iionreihe erhalten kann, wenn man den 1 . 4 - Di - p - toluidino - anthrachinon-6-carbon- säuremethylester so lange mit einem sulfo- nierend wirkenden Mittel behandelt, bis eine aufgearbeitete Probe völlig wasserlöslich ge worden ist. .
Der erhaltene Farbstoff färbt Wolle aus schwach saurem Bade in klaren grünen Tö nen von ausgezeichneten Echtheitseigen schaften.
<I>Beispiel:</I> 10 Teile 1.4-Di-p-toluidino-anthrachinon- 6-carbonsäuremethylester (hergestellt zumBei- spiel durch Erhitzen des 1. 4-Dichloranthra- chinon-6-carbonsäuremethylesters mit p-To- luidin bei Gegenwart von wasserfreiem Ka- liumacetat und wenig Kupferacetat auf etwa 140' C) werden bei etwa 5 bis 10 C in 100 Teilen rauchender Schwefelsäure, ent haltend 5 % S03, gelöst, worauf so lange rauchende Schwefelsäure, enthaltend 23/'0 S03, zugegeben wird,
bis eine aufgearbeitete Probe in kaltem Wasser eben völlig löslich geworden ist. Man giesst darnach unter Rüh ren in 1000 Teile Eiswasser, trennt den ent standenen Niederschlag ab, löst diesen in etwa 200 Teilen heissem Wasser und salzt den Farbstoff mit Kochsalz aus.
Process for the preparation of a dye of the anthracliinone series. The main patent relates to a process for the production of a dye of the anti-quinone series, in which the 1. 4-di-p-toluidinoanthraquinone - 2) - carboxylic acid methyl ester is treated with a sulfonating agent until a processed sample has become completely water-soluble.
It has now been found that a similarly valuable dye of the anthraquinone series can be obtained if the 1. 4 - Di - p - toluidino - anthraquinone-6-carboxylic acid methyl ester treated with a sulfonating agent until a prepared sample has become completely water-soluble. .
The dye obtained dyes wool from a weakly acidic bath in clear green tones with excellent fastness properties.
<I> Example: </I> 10 parts of 1,4-di-p-toluidino-anthraquinone-6-carboxylic acid methyl ester (prepared for example by heating the 1,4-dichloroanthraquinone-6-carboxylic acid methyl ester with p-toluidine The presence of anhydrous potassium acetate and a little copper acetate at about 140 ° C. are dissolved in 100 parts of fuming sulfuric acid containing 5% SO3 at about 5 to 10 ° C., whereupon fuming sulfuric acid containing 23/0 SO3 is added becomes,
until a processed sample has just become completely soluble in cold water. It is then poured into 1000 parts of ice water with stirring, the precipitate formed is separated off, dissolved in about 200 parts of hot water and the dye is salted out with sodium chloride.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE184187X | 1934-12-20 | ||
CH180697T | 1935-01-16 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH184187A true CH184187A (en) | 1936-05-15 |
Family
ID=25720456
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH184187D CH184187A (en) | 1934-12-20 | 1935-01-16 | Process for the preparation of a dye of the anthraquinone series. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH184187A (en) |
-
1935
- 1935-01-16 CH CH184187D patent/CH184187A/en unknown
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