CH97364A - Process for the preparation of a condensation product of the anthraquinone series which can be used as dye and dye intermediate. - Google Patents
Process for the preparation of a condensation product of the anthraquinone series which can be used as dye and dye intermediate.Info
- Publication number
- CH97364A CH97364A CH97364DA CH97364A CH 97364 A CH97364 A CH 97364A CH 97364D A CH97364D A CH 97364DA CH 97364 A CH97364 A CH 97364A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- condensation product
- orange
- preparation
- cold
- Prior art date
Links
- 239000007859 condensation product Substances 0.000 title claims description 6
- 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
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- 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
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 238000009835 boiling Methods 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- KXOGXZAXERYOTC-UHFFFAOYSA-N 1-amino-4-methoxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=CC=C2OC KXOGXZAXERYOTC-UHFFFAOYSA-N 0.000 claims 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical class [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 239000012265 solid product 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
- 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
- C09B1/36—Dyes with acylated amino groups
- C09B1/46—Dyes with acylated amino groups the acyl groups being residues of cyanuric acid or an analogous heterocyclic compound
- C09B1/467—Dyes with acylated amino groups the acyl groups being residues of cyanuric acid or an analogous heterocyclic compound attached to two or more anthraquinone rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Darstellung eines als Farbstoff und Farbstoffzwischenprodukt verwendbaren Kondensationsproduktes der Anthr achinonr eihe. Es wurde gefunden, dass man ein neues, als Farbstoff und Farbstoffzwischenprodukt verwendbares Kondensationsprodukt der An- thrachinonreihe erhält,
wenn man Cyanur- chlorid mit 1-Aminoanthrachinon und 1- Amino-4-11Zethoxy-Anthraehinon umsetzt.
<I>Beispiel:</I> 24 Teile 1-Aminoanthrachinon werden mit 22,5 Teilen Cyanurchlorid in 200 Teilen Ni- trobenzol während einer halben Stunde auf 190 bis 200' erwärmt. Dann wird abgekühlt und die breiige Masse filtriert. Das auf dem Filter zurückbleibende feste Produkt wird mit zirka 300 Teilen Nitrobenzol verrührt und nach Zusatz von 42 Teilen 1-Amino-4- DZethoxy-Anthrachinon während 11 Stunden auf zirka<B>100'</B> gehalten, wobei nach etwa der zehnten Stunde 40 Teile entwässertes Na triumacetat zugegeben werden.
Schliesslich erwärmt man noch während ungefähr 24 Stunden auf 115 bis 120, worauf nach Abkühlen das ausgeschiedene Kondensations- produkt abfiltriert, gewaschen und getrock net -wird. Es ist ein orangefarbenes Pulver, unlöslich üi Wasser, sehr wenig löslich in kaltem und heissem Alkohol, mässig löslich in kaltem, etwas besser in siedendem Nitroben- zol mit gelber Farbe, löslich in kalter kon zentrierter Schwefelsäure mit rotoranger Farbe und liefert eine rotorange Küpe, aus welcher Baumwolle in orangefarbenen Tö nen angefärbt wird.
Process for the preparation of a condensation product of the anthraquinone series which can be used as dye and dye intermediate. It has been found that a new condensation product of the anthrachinone series which can be used as dye and dye intermediate is obtained,
when cyanuric chloride is reacted with 1-aminoanthraquinone and 1- amino-4-11zethoxy-anthraquinone.
<I> Example: </I> 24 parts of 1-aminoanthraquinone are heated with 22.5 parts of cyanuric chloride in 200 parts of nitrobenzene to 190 to 200 ° for half an hour. It is then cooled and the pasty mass is filtered. The solid product remaining on the filter is stirred with about 300 parts of nitrobenzene and, after addition of 42 parts of 1-amino-4-Dzethoxy-anthraquinone, is kept at about 100 'for 11 hours, after about the tenth Hour 40 parts of dehydrated sodium acetate are added.
Finally, the mixture is heated to 115 to 120 for about 24 hours, after which, after cooling, the precipitated condensation product is filtered off, washed and dried. It is an orange-colored powder, insoluble in water, very slightly soluble in cold and hot alcohol, moderately soluble in cold, somewhat better in boiling nitrobenzene with a yellow color, soluble in cold concentrated sulfuric acid with a red-orange color and provides a red-orange vat, which cotton is dyed in orange tones.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH97364T | 1921-05-30 | ||
| CH97059T | 1921-05-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH97364A true CH97364A (en) | 1923-02-01 |
Family
ID=25705187
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH97364D CH97364A (en) | 1921-05-30 | 1921-05-30 | Process for the preparation of a condensation product of the anthraquinone series which can be used as dye and dye intermediate. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH97364A (en) |
-
1921
- 1921-05-30 CH CH97364D patent/CH97364A/en unknown
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