CH191015A - Process for the production of a vat dye of the anthraquinone carbazole series. - Google Patents
Process for the production of a vat dye of the anthraquinone carbazole series.Info
- Publication number
- CH191015A CH191015A CH191015DA CH191015A CH 191015 A CH191015 A CH 191015A CH 191015D A CH191015D A CH 191015DA CH 191015 A CH191015 A CH 191015A
- Authority
- CH
- Switzerland
- Prior art keywords
- production
- parts
- dye
- vat
- carbazole series
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 239000000984 vat dye Substances 0.000 title claims description 4
- VNGZQMYDWYDBDQ-UHFFFAOYSA-N anthracene-9,10-dione;9h-carbazole Chemical class C1=CC=C2C3=CC=CC=C3NC2=C1.C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 VNGZQMYDWYDBDQ-UHFFFAOYSA-N 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 10
- 239000000975 dye Substances 0.000 claims description 8
- DUJPMUKIEFLXRE-UHFFFAOYSA-N 1,4,5,8-tetrachloroanthracene-9,10-dione Chemical compound O=C1C2=C(Cl)C=CC(Cl)=C2C(=O)C2=C1C(Cl)=CC=C2Cl DUJPMUKIEFLXRE-UHFFFAOYSA-N 0.000 claims description 3
- 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
- 150000003839 salts Chemical class 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 235000002639 sodium chloride Nutrition 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- BZSXEZOLBIJVQK-UHFFFAOYSA-N 2-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1C(O)=O BZSXEZOLBIJVQK-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 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
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
- C09B5/26—Carbazoles of the anthracene series
- C09B5/28—Anthrimide carbazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines Küpenfarbstoffes der Anthr achinoncarbazolreihe. Es wurde gefunden, dass man einen Küpen- farbstoff der Anthrachinoncarbazolreihe her stellen kann, wenn man 1, 4, 5, 8-Penta- anthrimid mit Aluminiumchlorid in Csegen- wart eines wasserlöslichen, inerten Salzes bei etwa- 100-150 verschmilzt.
Der erhältliche Farbstoff stellt ein dunkles Pulver dar, das sich in konzentrierter Schwefel säure mit blauer Farbe löst und Baumwolle aus rotgefärbter Küpe in kräftigen, sehr ech ten gelboliven Tönen färbt.
Das dem vorliegenden Verfahren als Aus gangsprodukt dienende 1, 4, 5, 8-Pentaanthri- mid kann beispielsweise durch Erhitzen von 1 Mol 1, 4, 5, 8-Tetrachloranthrachinon mit 4 Mol 1-Aminoanthrachirion in Gegenwart eines Lösungsmittels, wie z. B. Nitrobenzol, sowie in Gegenwart von salzsäurebindenden Mitteln, wie z. B. Kalium- oder Natriumear- bonat, und Kupfersalzen erhalten werden.
Geeignete wasserlösliche, inerte Salze sind beispielsweise Natriumchlorid oder Kalium chlorid. <I>Beispiel 1:</I> 100 Teile wasserfreies Aluminiumchlorid und 12 Teile trockenes Kochsalz werden bei 120-130 geschmolzen. Bei dieser Tempera tur trägt man in kleinen Portionen innerhalb 1 bis 2 Stunden 20 Teile 1, 4, 5, 8-Penta- anthrimid ein und rührt 1 bis 2 Stunden weiter. Die Schmelze wird dann in etwa 1500 Teile Wasser eingetragen, aufgekocht und der Farbstoff durch Filtration isoliert. <I>Beispiel 2:</I> 100 Teile wasserfreies Aluminiumchlorid und 12 Teile trockenes Kochsalz werden bei 140-150 geschmolzen.
Bei dieser Tempera tur trägt man in kleinen Portionen innerhalb 1 Stunde 20 Teile 1, 4, 5, 8-Pentaanthrimid ein und rührt eine halbe Stunde weiter. Die Schmelze wird dann auf etwa 1500 Teile Wasser ausgetragen. Die so erhaltene Farb- stoffsuspension wird nun auf<B>90-950</B> geheizt und mit 50 Teilen konzentrierter technischer Salzsäure, 30 >ig, versetzt. Man lässt hierauf bei der gleichen Temperatur 5 Teile Natrium chlorat, gelöst in 50 Teilen Wasser, zutropfen. Der Farbstoff, der mit dem nach Beispiel 1 erhältlichen Produkt identisch ist, wird noch warm durch Filtration isoliert.
<I>Beispiel 3:</I> 100 Teile wasserfreies Aluminiumchlorid, 12 Teile trockenes Kochsalz werden geschmol zen. Unter Rühren trägt man dann bei 120 bis 125 20 Teile 1, 4, 5, 8-Pentaanthrimid, erhältlich z. B. durch Umsetzung von 1 Mol 1, 4, 5, 8-Tetrachloranthrachinon mit 4 Mol 1-Aminoanthrachinon, innerhalb etwa 1 Stunde ein und rührt noch eine halbe Stunde weiter. Die Schmelze wird dann auf Wasser ausge tragen und der gebildete Farbstoff, der mit dem nach Beispiel 1 erhältlichen Produkte übereinstimmt, durch Filtration isoliert.
Process for the production of a vat dye of the anthracinone carbazole series. It has been found that a vat dye of the anthraquinone carbazole series can be produced if 1, 4, 5, 8-penta-anthrimide is fused with aluminum chloride in the presence of a water-soluble, inert salt at about 100-150.
The available dye is a dark powder that dissolves in concentrated sulfuric acid with a blue color and dyes cotton from a red-dyed vat in strong, very real yellow-olive tones.
The present process as a starting product from 1, 4, 5, 8-pentaanthrimide can, for example, by heating 1 mole of 1, 4, 5, 8-tetrachloroanthraquinone with 4 moles of 1-aminoanthraquinone in the presence of a solvent such. B. nitrobenzene, as well as in the presence of hydrochloric acid binding agents such. B. potassium or sodium carbonate, and copper salts can be obtained.
Suitable water-soluble, inert salts are, for example, sodium chloride or potassium chloride. <I> Example 1: </I> 100 parts of anhydrous aluminum chloride and 12 parts of dry common salt are melted at 120-130. At this temperature, 20 parts of 1, 4, 5, 8-penta-anthrimide are introduced in small portions within 1 to 2 hours and stirring is continued for 1 to 2 hours. The melt is then introduced into about 1500 parts of water, boiled and the dye is isolated by filtration. <I> Example 2: </I> 100 parts of anhydrous aluminum chloride and 12 parts of dry common salt are melted at 140-150.
At this temperature, 20 parts of 1, 4, 5, 8-pentaanthrimide are added in small portions over the course of 1 hour and stirring is continued for half an hour. The melt is then discharged onto about 1500 parts of water. The dye suspension thus obtained is now heated to 90-950 and mixed with 50 parts of concentrated technical grade hydrochloric acid, 30%. 5 parts of sodium chlorate, dissolved in 50 parts of water, are then added dropwise at the same temperature. The dye, which is identical to the product obtainable according to Example 1, is isolated by filtration while still warm.
<I> Example 3: </I> 100 parts of anhydrous aluminum chloride, 12 parts of dry common salt are melted. While stirring, 20 parts of 1, 4, 5, 8-pentaanthrimide, obtainable z. B. by reacting 1 mole of 1, 4, 5, 8-tetrachloroanthraquinone with 4 moles of 1-aminoanthraquinone, within about 1 hour and stir for another half hour. The melt is then carried out on water and the dye formed, which corresponds to the product obtainable according to Example 1, isolated by filtration.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH191015T | 1936-06-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH191015A true CH191015A (en) | 1937-05-31 |
Family
ID=4437374
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH191015D CH191015A (en) | 1936-06-27 | 1936-06-27 | Process for the production of a vat dye of the anthraquinone carbazole series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH191015A (en) |
-
1936
- 1936-06-27 CH CH191015D patent/CH191015A/en unknown
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