CH100397A - 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
- CH100397A CH100397A CH100397DA CH100397A CH 100397 A CH100397 A CH 100397A CH 100397D A CH100397D A CH 100397DA CH 100397 A CH100397 A CH 100397A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- red
- condensation product
- soluble
- preparation
- Prior art date
Links
- 239000007859 condensation product Substances 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- 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 description 3
- 150000004056 anthraquinones Chemical class 0.000 title description 3
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 5
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 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
- 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 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000005406 washing 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Darstellung eines als Farbstoff und Farbstoffzwischenprodukt verwendbaren Kondensationsproduktes der Anthrachinonreihe. Es wurde gefunden, dass man ein neues, als Farbstoff und Farbstoffzwisthen@produlkt verwendbares Kondensationsprodukt der An- thrachinonreilie erhält, wenn man Cyanur- chlorid mit 1-Amino-4-methoxy-anthrachinon nebst Ammoniak umsetzt.
Beispiel: :i Teile 1-Amino-4-methoxy-anthrachinon erden mit etwa 40 Teilen Nitrobenzol auf -111 erwärmt. Dann werden 1,85 Teile Cyanur- clilorid zugefügt und unter Rühren während fünf Stunden auf<B>100'</B> geheizt, unter Zugabe von 0,8 Teilen calcinierter Soda nach Ablauf der eisten drei. Stunden.
Hierauf werden wei- <U>_</U> te@r0,9 Teile 1 - Amino - 4 - methoxy-anthra- ehinon zugesetzt und nochmals 6 Stunden bei 100 durchgerührt unter Zugabe von weiteren 5,2 Teilen ca.lcinierter Soda nach Ablauf von fünf Stunden.
Nachdem dann noch während 2-1 Stunden bei einer Temperatur von 120 bis 125 gehalten worden ist, wird bei dieser Temperatur etwa 14 Stunden lang ein lang samer Strom trockenen Ammoniakgases ein- geleitet-.
Schliesslich wird abgekühlt und das ausgeschiedene Kondensationsprodukt von der Nitrobenzollösung abfiltriert. Nach Waschen mit etwas frischem Nitrobenzol und darauf mit Alkohol und Wasser und Trocknen, stellt es ein rotes Pulver vor, unlöslich in Wasser, wenig löslich in Alkohol, wenig bezw. mässig löslich in kaltem bezw. heissem Chlorbenzol mit rotoranger Farbe, wenig bezw. ziemlich gut löslich in kaltem bezw. siedendem Nitro- benzol mit tief rotoranger Farbe,
löslich in konzentrierter Schwefelsäure mit bräunlich- roter Farbe. Seine Küpenlösung zeigt rot orange Färbung, in ihr gefärbte Baumwolle hat nachdem Verhängen Scharlachtöne.
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 anthraquinone purity which can be used as a dye and dye twisthen product is obtained if cyanuric chloride is reacted with 1-amino-4-methoxy-anthraquinone together with ammonia.
Example: i part 1-amino-4-methoxy-anthraquinone ground with about 40 parts nitrobenzene heated to -111. Then 1.85 parts of cyanuric chloride are added and the mixture is heated to 100% for five hours with stirring, with 0.8 part of calcined soda being added after the last three hours. Hours.
A further 0.9 parts of 1-amino-4-methoxy-anthraquinone are then added and the mixture is stirred for a further 6 hours at 100 with the addition of a further 5.2 parts of about iced soda Five hours have passed.
After the temperature has been kept at a temperature of 120 to 125 for 2-1 hours, a slow stream of dry ammonia gas is introduced at this temperature for about 14 hours.
Finally, it is cooled and the precipitated condensation product is filtered off from the nitrobenzene solution. After washing with a little fresh nitrobenzene and then with alcohol and water and drying, it turns out to be a red powder, insoluble in water, little soluble in alcohol, little respectively. moderately soluble in cold resp. hot chlorobenzene with red-orange color, little resp. fairly soluble in cold resp. boiling nitrobenzene with a deep red-orange color,
soluble in concentrated sulfuric acid with a brownish-red color. His vat solution shows a red-orange coloration, while cotton dyed in it has scarlet tones after impregnation.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH97059T | 1921-05-30 | ||
| CH100397T | 1923-01-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH100397A true CH100397A (en) | 1923-07-16 |
Family
ID=25705193
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH100397D CH100397A (en) | 1921-05-30 | 1923-01-02 | 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) | CH100397A (en) |
-
1923
- 1923-01-02 CH CH100397D patent/CH100397A/en unknown
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