CH147799A - Process for the preparation of a vat dye. - Google Patents
Process for the preparation of a vat dye.Info
- Publication number
- CH147799A CH147799A CH147799DA CH147799A CH 147799 A CH147799 A CH 147799A CH 147799D A CH147799D A CH 147799DA CH 147799 A CH147799 A CH 147799A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- condensation
- blue
- vat
- vat dye
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 5
- 239000000984 vat dye Substances 0.000 title claims description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 3
- 235000011118 potassium hydroxide Nutrition 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- -1 anthraquinonyl - amino - benzanthronyl pyrazolanthrone Chemical compound 0.000 claims description 2
- 239000003518 caustics Substances 0.000 claims description 2
- 235000019441 ethanol Nutrition 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 claims 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 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 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- NAJSRBSTKPARDW-UHFFFAOYSA-N C1=CC=CC=2CC3=CC=CC=C3C(C12)=O.N1N=CC=C1.C1=CC=C2C=CC=C3C(=O)C4=CC=CC=C4C1=C23 Chemical class C1=CC=CC=2CC3=CC=CC=C3C(C12)=O.N1N=CC=C1.C1=CC=C2C=CC=C3C(=O)C4=CC=CC=C4C1=C23 NAJSRBSTKPARDW-UHFFFAOYSA-N 0.000 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 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229940072033 potash Drugs 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- HUKPVYBUJRAUAG-UHFFFAOYSA-N 7-benzo[a]phenalenone Chemical class C1=CC(C(=O)C=2C3=CC=CC=2)=C2C3=CC=CC2=C1 HUKPVYBUJRAUAG-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 150000008425 anthrones Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 229940116318 copper carbonate Drugs 0.000 description 1
- GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical compound [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-UHFFFAOYSA-L 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003254 radicals Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Coloring (AREA)
Description
Verfahren zur Darstellung eines Küpenfarbstoffes. Indem Hauptpatent Nr. 128473 und den Zusätzen Nr. 13126:4 bis 131267, sowie 131730 sind Verfahren zur Darstellung von Küpenfarbstoffen beschrieben, nach denen man Bz-1-Benzanthronyl-Py-l-pyrazolan- throne mittelst Alkali zu Bz-1-Py-1-/-2-2'- Benz.anthronpyrazol:anthronen kondensiert.
Wir haben nun gefunden, dass man :diese Reaktion auch auf solche Bz- 1-Benzanthronyl- Py-l-pyrazolanthrone übertragen kann, die substituierte Aminoreste der verschiedensten Art im Molekül enthalten, wobei zum Bei spiel der angegliederte Stickstoff des Restes auch selbst wieder Teil eines heterocyclischen Ringes sein kann.
In manchen Fällen dürften nach diesem neuen; Verfahren in den Kali schmelzen neben den: Ringschlüssen zum Benz anthron-pyrazolanthronderivat auch noch wei tere Ringschlüsse erfolgen, zum Beispiel unter Bildung besonders wertvoller Carbazol- oder Akridonabkömmlinge der Benzanthron- pyrazolanthrone.
Gegenstand dieses Patentes ist ein Ver- fahren zur Darstellung eines Küpenfarb- stoffes, welches dadurch gelzennzeichnet ist, dass man ein Anthrachinonyl-amino-benzan- thronylpyrazolanthron von der folgenden Formel
EMI0001.0029
(erhältlich durch Kondensation von 1 Mol. Bz-1-6-Dibrombenzanthron mit 1 Mol. Py r a.zolanthron und 1 Mol. 1-Aminoanthrachinon)
mittelst Atzalkali in Gegenwart eines Alko hols bei erhöhter Temperatur, zum Beispiel <B>90'</B> bis<B>100',</B> kondensiert. <I>Beispiel:</I> 55 Gewichtsteile Pyrazolanthron und 20 Gewichtsteile feinverteilte Pottasche werden in 1300 Volumteilen Nitrobenzol 2 Stunden lang bei etwa 195 Ülbadtemperatur ver rührt; es bildet sich das rote Kalisalz des Pyrazolanthrons. Dann werden 97 Gewichts teile dibromiertes Benzanthron eingetragen und während 4 Stunden unter Rühren zum Kochen erhitzt.
Das Reaktionsgemisch ent hält nun Monobrom-Bz-l-Benzanthronyl-Py- 1-pyrazolanthron. Man lässt ein wenig ab kühlen, rührt weiter ein Gemisch von 56 Gewichtsteilen 1-Aminoanthrachinon, 56 Ge wichtsteilen wasserfreiem Natriumacetat und 20 Gewichtsteilen Kupferkarbonat ein und erhitzt wieder 16 Stunden lang zum Sieden. Nach dem Erkalten scheidet sich .das schwer lösliche Kondensationsprodukt in glänzenden, schokoladebraunen Kriställehen aus. Es wird auf ein Filter gebracht und mit Nitro- benzol, Alkohol und Wasser gewaschen.
Noch vorhandenes Kupfersalz wird durch Auskochen mit verdünnter Salzsäure entfernt und das Produkt getrocknet. Das so gewon nene Anthrachinonylamino-Bz-l-Benzanthro- nyl-Py-l-pyrazolanthron gibt in konzentrier ter Schwefelsäure eine braungelbe Lösung, aus der beim Verdünnen mit Wasser rotgelbe Flocken ausfallen.
100 Gewichtsteile dieses Anthrachinouyl- amino-Benzanthronyl-pyrazolanthrons wer den mit 500 Gewichtsteilen Ätzkali und 400 Gewichtsteilen Alkohol unter Rühren etwa 7-8 Stunden lang bei 98 bis 100 C ver schmolzen. Dann wird in Wasser ausgegos sen und die Fällung des gebildeten Farbstof fes, der zum Teil als Leukoverbindung ge löst vorliegt, durch Ausoxyd.ation mittelst Luft vervollständigt. Nach der Filtration und dem Auswaschen erhält man eine nahe zu schwarze Paste, die nach dem Trocknen ein schwarzes Parbstoffpulver bildet.
Das Produkt löst sieh mit grüner Farbe in kon zentrierter Schwefelsäure. Wasser fällt aus dieser Lösung blaugraue Flocken. Aus einer blauen alkalischen Hydrosufitküpe wird Baumwolle in grüns.tichig blaugrauen Tönen von vorzüglicher Echtheit angefärbt.
Process for the preparation of a vat dye. The main patent No. 128473 and the additions No. 13126: 4 to 131267 and 131730 describe processes for the preparation of vat dyes, according to which Bz-1-benzanthronyl-Py-1-pyrazolan-thrones can be converted to Bz-1-Py by means of alkali -1 - / - 2-2'- benz.anthronpyrazole: anthrones condensed.
We have now found that: this reaction can also be transferred to those Bz-1-benzanthronyl-Py-l-pyrazole anthrones which contain various types of substituted amino radicals in the molecule, with the nitrogen attached to the radical also being part of it, for example of a heterocyclic ring.
In some cases you are likely to look for this new; Processes in the potash melt in addition to the: ring closures to the benzanthrone pyrazole anthrone derivative, further ring closures take place, for example with the formation of particularly valuable carbazole or akridone derivatives of the benzanthrone pyrazole anthrones.
The subject of this patent is a process for the preparation of a vat dye which is characterized in that an anthraquinonyl-aminobenzanthronylpyrazolanthrone of the following formula is used
EMI0001.0029
(obtainable by condensation of 1 mol. Bz-1-6-dibromobenzanthrone with 1 mol. pyra.zolanthrone and 1 mol. 1-aminoanthraquinone)
by means of caustic alkali in the presence of an alcohol at elevated temperature, for example <B> 90 '</B> to <B> 100', </B> condensed. <I> Example: </I> 55 parts by weight of pyrazolanthrone and 20 parts by weight of finely divided potash are stirred in 1,300 parts by volume of nitrobenzene for 2 hours at a bath temperature of about 195; the red potassium salt of pyrazolanthrone is formed. Then 97 parts by weight of dibrominated benzanthrone are entered and heated to the boil for 4 hours with stirring.
The reaction mixture now contains monobromo-Bz-1-benzanthronyl-Py-1-pyrazolanthrone. The mixture is allowed to cool a little, a mixture of 56 parts by weight of 1-aminoanthraquinone, 56 parts by weight of anhydrous sodium acetate and 20 parts by weight of copper carbonate are stirred in and heated again to the boil for 16 hours. After cooling, the sparingly soluble condensation product separates out in shiny, chocolate-brown crystals. It is placed on a filter and washed with nitrobenzene, alcohol and water.
Any copper salt still present is removed by boiling with dilute hydrochloric acid and the product is dried. The anthraquinonylamino-Bz-1-benzantronyl-Py-1-pyrazolanthrone obtained in this way gives a brownish-yellow solution in concentrated sulfuric acid, from which red-yellow flakes precipitate when diluted with water.
100 parts by weight of this anthraquinouyl-amino-benzanthronyl-pyrazolanthrons who melted the with 500 parts by weight of caustic potash and 400 parts by weight of alcohol with stirring for about 7-8 hours at 98 to 100 ° C. It is then poured into water and the precipitation of the dye formed, which is partly dissolved as a leuco compound, is completed by oxidation with air. After filtration and washing out, a paste that is almost black is obtained which, after drying, forms a black paraffin powder.
The product dissolves in concentrated sulfuric acid with a green color. Water falls from this solution blue-gray flakes. Cotton is dyed from a blue alkaline hydrosufit vat in greenish blue-gray tones of excellent fastness.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE147799X | 1929-03-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH147799A true CH147799A (en) | 1931-06-30 |
Family
ID=5672239
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH147799D CH147799A (en) | 1929-03-04 | 1930-02-26 | Process for the preparation of a vat dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH147799A (en) |
-
1930
- 1930-02-26 CH CH147799D patent/CH147799A/en unknown
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