CH100706A - Process for the preparation of a vat dye. - Google Patents
Process for the preparation of a vat dye.Info
- Publication number
- CH100706A CH100706A CH100706DA CH100706A CH 100706 A CH100706 A CH 100706A CH 100706D A CH100706D A CH 100706DA CH 100706 A CH100706 A CH 100706A
- Authority
- CH
- Switzerland
- Prior art keywords
- red
- preparation
- vat dye
- vat
- violet
- Prior art date
Links
- 239000000984 vat dye Substances 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 8
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- GRWZHXKQBITJKP-UHFFFAOYSA-N dithionous acid Chemical group OS(=O)S(O)=O GRWZHXKQBITJKP-UHFFFAOYSA-N 0.000 claims description 2
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 235000005811 Viola adunca Nutrition 0.000 claims 1
- 240000009038 Viola odorata Species 0.000 claims 1
- 235000013487 Viola odorata Nutrition 0.000 claims 1
- 235000002254 Viola papilionacea Nutrition 0.000 claims 1
- 239000000975 dye Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- RFNNAQCNVLPJFX-UHFFFAOYSA-N carboxy carboxyoxycarbonyl carbonate;perylene Chemical compound OC(=O)OC(=O)OC(=O)OC(O)=O.C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 RFNNAQCNVLPJFX-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- NOJYTLULJKTWHE-UHFFFAOYSA-N perylene 1,3,5,7-tetraoxocane-2,4,6,8-tetrone Chemical compound O=C1OC(=O)OC(=O)OC(=O)O1.C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 NOJYTLULJKTWHE-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C09B5/62—Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
Verfahren zur Darstellung eines Nüpenfarbstoffes. Es ist gefunden worden, dass die Perylen- 3. .f . 9 . 10-Tetracarbons < iure sich mit Am- inoniak oder Aminen kondensiert und dass dabei wertvolle Küpenfarbstoffe entstehen. Gegenstand dieses Hauptpatentes ist die Dar stellung eines Küpenfarbstoffes aus Perylen- tetracarbonsäure und Anilin.
Beispiel 392 Gewichtsteile Perylentetracarbon- , nhydrid werden mit etwa 3000 Ge <I>s</I> äurea wiehtsteilen Anilin unter Rühren auf etwa <B>185</B> bis zum Verschwinden des Perylen- tetracarboiis".iureanhydrids erhitzt. Das Kon densationsprodukt scheidet sich dabei kristal- liniseli ab. Nach beendeter Kondensation lässt man etwas abkühlen und drückt dann in ver dünnte Salzsäure, die das überschüssige Ani lin aufnimmt.
Man filtriert sodann den Farb stoff ab, wäscht mit Wasser nach und zieht schliesslich mit heisser, verdünnter Kalilauge zur Entfernung geringer alkalilöslicher Ver unreinigungen aus. Die Ausbeute ist fast quantitativ. Der Farbstoff wird in braunroten Kristall nadeln erhalten. - Seine Lösung in konzen trierter Schwefelsäure erscheint in dicker Schicht violett, in dünner Schicht blau ge färbt; sie fluoresziert rot.
Mit alkalischem Hydrosulfit erhält man eine rotviolette Küpe, aus der Baumwolle in echten roten Tönen ausgefärbt wird.
Process for the preparation of a pebble dye. It has been found that the perylene 3. .f. 9. 10-tetracarboxylic acid condenses with ammonia or amines and valuable vat dyes are formed. The subject of this main patent is the presentation of a vat dye made from perylenetetracarboxylic acid and aniline.
EXAMPLE 392 parts by weight of perylene tetracarbonic anhydride are heated with about 3000 parts by weight of aniline with stirring to about 185 until the perylene tetracarbonic acid has disappeared. The condensation product After the condensation has ended, the mixture is allowed to cool down a little and then pressed into dilute hydrochloric acid, which absorbs the excess aniline.
The dye is then filtered off, rewashed with water and finally drawn off with hot, dilute potassium hydroxide solution to remove minor alkali-soluble impurities. The yield is almost quantitative. The dye is obtained in brown-red crystal needles. - Its solution in concentrated sulfuric acid appears violet in a thick layer and blue in a thin layer; it fluoresces red.
With alkaline hydrosulphite you get a red-violet vat, from which cotton is dyed in real red tones.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH100706T | 1923-01-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH100706A true CH100706A (en) | 1923-08-16 |
Family
ID=4359004
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH100706D CH100706A (en) | 1923-01-03 | 1923-01-03 | Process for the preparation of a vat dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH100706A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2543747A (en) * | 1948-08-27 | 1951-03-06 | Gen Aniline & Film Corp | Preparation of n.n'-diaryl derivatives of perylene diimid |
-
1923
- 1923-01-03 CH CH100706D patent/CH100706A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2543747A (en) * | 1948-08-27 | 1951-03-06 | Gen Aniline & Film Corp | Preparation of n.n'-diaryl derivatives of perylene diimid |
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