DE493813C - Process for the preparation of Kuepen dyes - Google Patents
Process for the preparation of Kuepen dyesInfo
- Publication number
- DE493813C DE493813C DEI35209D DEI0035209D DE493813C DE 493813 C DE493813 C DE 493813C DE I35209 D DEI35209 D DE I35209D DE I0035209 D DEI0035209 D DE I0035209D DE 493813 C DE493813 C DE 493813C
- Authority
- DE
- Germany
- Prior art keywords
- parts
- preparation
- dyes
- dye
- sulfuric acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 4
- 239000000975 dye Substances 0.000 title description 11
- 238000002360 preparation method Methods 0.000 title description 2
- ACPOUJIDANTYHO-UHFFFAOYSA-N anthra[1,9-cd]pyrazol-6(2H)-one Chemical compound C1=CC(C(=O)C=2C3=CC=CC=2)=C2C3=NNC2=C1 ACPOUJIDANTYHO-UHFFFAOYSA-N 0.000 claims description 4
- 239000000984 vat dye Substances 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229940072033 potash Drugs 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 235000005811 Viola adunca Nutrition 0.000 description 1
- 240000009038 Viola odorata Species 0.000 description 1
- 235000013487 Viola odorata Nutrition 0.000 description 1
- 235000002254 Viola papilionacea Nutrition 0.000 description 1
- 244000172533 Viola sororia Species 0.000 description 1
- CKUAXEQHGKSLHN-UHFFFAOYSA-N [C].[N] Chemical group [C].[N] CKUAXEQHGKSLHN-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010626 work up procedure Methods 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
- C09B5/02—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic ring being only condensed in peri position
- C09B5/04—Pyrazolanthrones
-
- 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
- C09B5/002—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being condensed in peri position and in 1-2 or 2-3 position
- C09B5/008—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being condensed in peri position and in 1-2 or 2-3 position only N-containing hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Darstellung von Küpenfarbstoffen Es wurde gefunden, daß neue Küpenfarbstoffe entstehen, wenn man Pyrazolanthron in Gegenwart von alkalischen Kondensationsmitteln mit. i Amino-a-halogenanthrachinonen oder deren Substitutionsprodukten in der Wärme behandelt. Man kann hierbei in GeL-enwart oder Abwesenheit von Katalysatoren arbeiten. Den Eigenschaften der neuen Farbstoffe nach dürfte hierbei nicht nur eine Stickstoff-Kohlenstoff-Verkettung unter Austritt von Halogenwasserstoff erfolgen, sondern eine weitere Kondensation, wahrscheinlich im Sinne der folgenden Formeln eintreten Die neuen Produkte sind kräftige Küpenfarbstoffe von guten Echtheitseigenschaften. Beispiel i i i Teile Pyrazolanthron werden zusammen mit 15,1 Teilen i Amino-z-bromanthrachinon, i o Teilen Pottasche, 0,5 Teilen Kupferpulver und zoo Teilen Nitrobenzol zum Sieden erhitzt, bis keine Vermehrung der Farbstoffbildung mehr eintritt. Man saugt noch warm ab und befreit das Ungelöste in bekannter Weise von Lösungsmitteln und Salzen. Der rohe Farbstoff wird zweckmäßig durch Umkristallisieren aus organischen Lösungsmitteln, z. B. o-Dichlorbenzol oder Trichlorbenzol, in denen er in der Hitze verhältnismäßig leicht löslich ist, gereinigt oder auch durch fraktionierte Fällung aus Schwefelsäure. Beim Verdünnen der Lösung des Rohprodukts in io Teilen konzentrierter Schwefelsäure mit 2o Teilen einer Schwefelsäure von 5o° B6 fällt der Hauptsache nach nur der reine Farbstoff aus. Man kann auch beide Verfahren der Reinigung kombinieren. In reinem Zustand ist der Farbstoff ein dunkles Pulver, welches sich in konzentriertem Schwefelsäure mit leuchtend blauer Farbe löst. Er färbt Baumwolle aus violetter Küpe in kräftig blauvioletten chlorechten Tönen.Process for the preparation of vat dyes It has been found that new vat dyes are produced when using pyrazole anthrone in the presence of alkaline condensing agents. i Amino-a-halogenanthraquinones or their substitution products treated with heat. You can work in the presence or absence of catalysts. According to the properties of the new dyes, not only should a nitrogen-carbon chain take place with the escape of hydrogen halide, but a further condensation, probably in the sense of the following formulas, should occur The new products are strong vat dyes with good fastness properties. Example iii parts of pyrazolanthrone are heated to boiling together with 15.1 parts of i amino-z-bromoanthraquinone, 10 parts of potash, 0.5 parts of copper powder and zoo parts of nitrobenzene until the formation of dye no longer increases. It is suctioned off while still warm and the undissolved material is freed from solvents and salts in a known manner. The crude dye is conveniently obtained by recrystallization from organic solvents, e.g. B. o-dichlorobenzene or trichlorobenzene, in which it is relatively easily soluble in the heat, purified or by fractional precipitation from sulfuric acid. When the solution of the crude product is diluted in 10 parts of concentrated sulfuric acid with 20 parts of sulfuric acid at 50 ° B6, in the main only the pure dye precipitates. You can also combine both methods of cleaning. In its pure state, the dye is a dark powder that dissolves in concentrated sulfuric acid with a bright blue color. He dyes cotton from a violet vat in strong blue-violet, chlorine-like shades.
Der Farbstoff bildet sich auch bei Abwesenheit von Katalysatoren. Beispiel 2 11 Teile Pyrazolanthron werden mit 15,9 Teilen i-Amino-2-brom-q.-oxyanthrachinon, io Teilen Pottasche und Zoo Teilen Nitrobenzol etwa 20 Stunden zum Sieden erhitzt. Die Aufarbeitung und die Reinigung des entstandenen Farbstoffes erfolgt in der in Beispiel i beschriebenen Weise. Der Farbstoff ist in reinem Zustand ein dunkles Pulver, welches sich in konzentrierter 'Schwefelsäure mit grünblauer Farbe löst. Er färbt Baumwolle aus blauer Küpe in tiefen blaugrünen Tönen an, die beim Chloren nach Grau umschlagen.The dye is also formed in the absence of catalysts. Example 2 1 1 pyrazolanthrone parts are heated with 15.9 parts of i-amino-2-bromo-Q.-oxyanthrachinon, io parts potash and Zoo parts of nitrobenzene about 20 hours to boiling. The work-up and the purification of the resulting dye are carried out in the manner described in Example i. In its pure state, the dye is a dark powder, which dissolves in concentrated sulfuric acid with a green-blue color. It dyes cotton from a blue vat in deep blue-green tones that turn gray when chlorinated.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI35209D DE493813C (en) | 1928-08-10 | 1928-08-10 | Process for the preparation of Kuepen dyes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI35209D DE493813C (en) | 1928-08-10 | 1928-08-10 | Process for the preparation of Kuepen dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE493813C true DE493813C (en) | 1930-03-14 |
Family
ID=7188923
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEI35209D Expired DE493813C (en) | 1928-08-10 | 1928-08-10 | Process for the preparation of Kuepen dyes |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE493813C (en) |
-
1928
- 1928-08-10 DE DEI35209D patent/DE493813C/en not_active Expired
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