AT55039B - Process for the preparation of vat dyes. - Google Patents
Process for the preparation of vat dyes.Info
- Publication number
- AT55039B AT55039B AT55039DA AT55039B AT 55039 B AT55039 B AT 55039B AT 55039D A AT55039D A AT 55039DA AT 55039 B AT55039 B AT 55039B
- Authority
- AT
- Austria
- Prior art keywords
- preparation
- vat dyes
- isatin
- parts
- halogenated
- 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
- 150000004056 anthraquinones Chemical class 0.000 claims description 3
- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 description 13
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- MQIUMARJCOGCIM-UHFFFAOYSA-N 1,5-dichloroanthracene-9,10-dione Chemical compound O=C1C2=C(Cl)C=CC=C2C(=O)C2=C1C=CC=C2Cl MQIUMARJCOGCIM-UHFFFAOYSA-N 0.000 description 1
- IIPRUQZTMZETSL-UHFFFAOYSA-N 1-bromo-4-(methylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(Br)=CC=C2NC IIPRUQZTMZETSL-UHFFFAOYSA-N 0.000 description 1
- ZGPFGHSOYPBCGI-UHFFFAOYSA-N 1-chloroindole-2,3-dione Chemical compound C1=CC=C2N(Cl)C(=O)C(=O)C2=C1 ZGPFGHSOYPBCGI-UHFFFAOYSA-N 0.000 description 1
- VCYBVWFTGAZHGH-UHFFFAOYSA-N 1-methylindole-2,3-dione Chemical compound C1=CC=C2N(C)C(=O)C(=O)C2=C1 VCYBVWFTGAZHGH-UHFFFAOYSA-N 0.000 description 1
- NJWGQARXZDRHCD-UHFFFAOYSA-N 2-methylanthraquinone Chemical class C1=CC=C2C(=O)C3=CC(C)=CC=C3C(=O)C2=C1 NJWGQARXZDRHCD-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 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 description 1
- 239000007859 condensation product Substances 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- -1 methyl isatins Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- SWGJCIMEBVHMTA-UHFFFAOYSA-K trisodium;6-oxido-4-sulfo-5-[(4-sulfonatonaphthalen-1-yl)diazenyl]naphthalene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].C1=CC=C2C(N=NC3=C4C(=CC(=CC4=CC=C3O)S([O-])(=O)=O)S([O-])(=O)=O)=CC=C(S([O-])(=O)=O)C2=C1 SWGJCIMEBVHMTA-UHFFFAOYSA-K 0.000 description 1
Landscapes
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Darstellung von Küpenfarbstoffen.
Es wurde die Beobachtung gemacht, dass Isatin, seine Homologen und Analogen sich mit halogensubstituierten Authrachinonen kondensieren lassen. Die entstehenden Produkte sind Küpenfarbstoffe von bemerkenswerter Echtheit. So liefert z. B. α-Chloranthrachinon mit Isatin, Methylisatin oder Chlorisatin blaustichig rote, 1.5-Dichloranthrachinon mit Isatin violette Farbstoffe, 1-Methylamino-4-bromanthrachinon mit Isatin einen blauen Farb-
EMI1.1
Reaktion mit aller Wahrscheinlichkeit nach folgender Gleichung formulieren :
EMI1.2
Beispiel 1.
24'3 Teile x-Chloranthrachinon werden mit 14'7 Teilen Isatin in 100 Teilen Nitro-
EMI1.3
chlorür zusetzt, mehrere Stunden zum Sieden erhitzt. Nach dem Erkalten saugt man ab, wobei man das Kondensationsprodukt in kristallinischer Form erhält. Dasselbe stellt ein blaurotes Pulver dar, welches in den meisten organischen Solventien ziemlich schwer liislich ist. In konzentrierter Schwefelsäure löst es sich mit gelbbrauner Farbe, beim Eingiessen der sehwefelsauren Lösung in Wasser scheidet es sich in roten Flocken ab. Mit Reduktionsmitteln liefert der Körper eine violettrote Küpe, aus der Baumwolle in blaustichig roten Tönen angefärbt wird. Der Farbstoff ist von hervorragender Chlorecbtheit.
Beispiel2.
27.7 Teile 1.5-Dichloranthrachinon werden mit 14.7 Teilen (1 Mol.) Isatin in 150 Teilen Nitroh enzol unter Zusatz von Natriumazetat und Kupferchlorür zum Sieden erhitzt und die Masse mehrere Stunden im Sieden erhalten. Nach dem Erkalten wird abgesaugt, mit Alkohol gewaschen und das Produkt nochmals durch Auskochen mit Wasser gereinigt. Es ist ein violettes Pulver, das in den meisten organischen Solventien ziemlich löslich ist. In konzentrierter Schwefelsäure löst es sich mit gelbbrauner Farbe ; diese Lösung scheidet beim Eingiessen in Wasser rote Flocken ab. Mit Reduktionsmitteln gibt es eine schmutzige
EMI1.4
i ist hervorragend chlorecht.
Beispiel 3.
EMI1.5
<Desc/Clms Page number 2>
Beispiel 4.
EMI2.1
wolle mit grtinstichig blauer Farbe an.
Ganz analog verläuft die Reaktion bei Anwendung kernsubstituierter Isatine und Isatinderivate, wie Methylisatine, halogenisierte Isatine, oder bei Verwendung anderer halogenisierter Anthrachinone oder halogenisierter Anthrachinonabkömmlinge, wie halogenisierte Anthrimide, halogenisierte 2-Methylanthrachinone usw.
<Desc / Clms Page number 1>
Process for the preparation of vat dyes.
It has been observed that isatin, its homologues and analogues condense with halogen-substituted authraquinones. The resulting products are vat dyes of remarkable authenticity. For example, B. α-Chloranthraquinone with isatin, methylisatin or chlorisatin bluish red, 1.5-dichloranthraquinone with isatin violet dyes, 1-methylamino-4-bromoanthraquinone with isatin a blue color
EMI1.1
In all probability, formulate the reaction according to the following equation:
EMI1.2
Example 1.
24'3 parts of x-chloranthraquinone are mixed with 14'7 parts of isatin in 100 parts of nitro
EMI1.3
chlorine added, heated to the boil for several hours. After cooling, the product is filtered off with suction, the condensation product being obtained in crystalline form. The same is a blue-red powder, which is rather difficult to dissolve in most organic solvents. It dissolves in concentrated sulfuric acid with a yellow-brown color; when the sulfuric acid solution is poured into water, it separates in red flakes. With reducing agents, the body delivers a purple-red vat from which cotton is dyed in blue-tinged red tones. The dye is extremely chlorine-free.
Example2.
27.7 parts of 1,5-dichloroanthraquinone are heated to boiling with 14.7 parts (1 mol.) Of isatin in 150 parts of nitrohenzene with the addition of sodium acetate and copper chloride and the mass is kept boiling for several hours. After cooling, it is filtered off with suction, washed with alcohol and the product is purified again by boiling with water. It is a purple powder that is quite soluble in most organic solvents. In concentrated sulfuric acid it dissolves with a yellow-brown color; this solution separates out red flakes when poured into water. With reducing agents there is a dirty one
EMI1.4
i has excellent chlorine law.
Example 3.
EMI1.5
<Desc / Clms Page number 2>
Example 4.
EMI2.1
wanted with grtinstichig blue color.
The reaction proceeds very analogously when using ring-substituted isatins and isatin derivatives such as methyl isatins, halogenated isatins, or when using other halogenated anthraquinones or halogenated anthraquinone derivatives such as halogenated anthrimides, halogenated 2-methylanthraquinones, etc.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE55039X | 1910-04-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT55039B true AT55039B (en) | 1912-08-26 |
Family
ID=5628237
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT55039D AT55039B (en) | 1910-04-27 | 1911-04-15 | Process for the preparation of vat dyes. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT55039B (en) |
-
1911
- 1911-04-15 AT AT55039D patent/AT55039B/en active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AT55039B (en) | Process for the preparation of vat dyes. | |
| DE236407C (en) | ||
| DE451549C (en) | Process for the preparation of green-coloring, sulphurous cow dyes | |
| DE650229C (en) | Process for the production of Kuepen dyes | |
| DE536294C (en) | Process for the preparation of Kuepen dyes of the anthraquinone series | |
| DE546228C (en) | Process for the production of nitrogen-containing Kuepen dyes | |
| DE451720C (en) | Process for the production of Kuepen dyes | |
| DE540931C (en) | Process for the production of real Kuepen dyes | |
| AT112610B (en) | Process for the preparation of vat dyes of the anthanthrone series. | |
| DE544917C (en) | Process for the representation of decoctions of the pyranthrone | |
| DE712447C (en) | Process for the production of Kuepen dyes of the anthraquinone series which contain the hydropyridine ring | |
| DE456763C (en) | Process for the preparation of Kuepen dyes | |
| DE469343C (en) | Process for the preparation of indigoid dyes | |
| DE744771C (en) | Process for the production of Kuepen dyes | |
| DE470501C (en) | Process for the production of dyes of the anthracene series | |
| DE487023C (en) | Process for the preparation of Kuepen dyes of the anthanthrone series | |
| DE598779C (en) | Process for the representation of dyes | |
| CH122071A (en) | Process for the preparation of a nitrogenous vat dye. | |
| CH143400A (en) | Process for the preparation of a vat dye. | |
| CH104013A (en) | Process for the preparation of a condensation product of the anthraquinone series which can be used as dye and dye intermediate. | |
| CH108211A (en) | Process for the preparation of a condensation product of the anthraquinone series which can be used as dye and dye intermediate. | |
| CH111931A (en) | Process for the preparation of a vat dye from nitrodibenzanthrone. | |
| DE1060072B (en) | Process for the production of Kuepen dyes | |
| CH196353A (en) | Process for the preparation of a pyrene derivative. | |
| CH259729A (en) | Process for the production of a vat dye. |