CH158129A - Process for the preparation of a nitrogenous anthraquinone derivative. - Google Patents
Process for the preparation of a nitrogenous anthraquinone derivative.Info
- Publication number
- CH158129A CH158129A CH158129DA CH158129A CH 158129 A CH158129 A CH 158129A CH 158129D A CH158129D A CH 158129DA CH 158129 A CH158129 A CH 158129A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- aminophenol
- nitrogenous
- anthraquinone derivative
- organic solvents
- Prior art date
Links
- 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 4
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- -1 nitrogenous anthraquinone Chemical class 0.000 title description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims description 8
- 239000000975 dye Substances 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 4
- KLYIJQCYEGQYMX-UHFFFAOYSA-N 4-aminophenol hypochlorous acid Chemical compound OCl.NC1=CC=C(O)C=C1 KLYIJQCYEGQYMX-UHFFFAOYSA-N 0.000 claims description 3
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 3
- 239000004327 boric acid Substances 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- 150000004056 anthraquinones Chemical class 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- FINOAUDUYKVGDS-UHFFFAOYSA-N (2-tert-butylcyclohexyl) acetate Chemical compound CC(=O)OC1CCCCC1C(C)(C)C FINOAUDUYKVGDS-UHFFFAOYSA-N 0.000 description 1
- 239000003638 chemical reducing agent Substances 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
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 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
- 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
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
- C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
- C09B1/325—Dyes with no other substituents than the amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 153492. Verfahren zur Darstellung eines stickstoffhaltigen Anthrachinonderivates. Es wurde gefunden, dass man einen grü nen Acetatseidefarbstoff erhält, wenn man 1-Oxy-4, 5, 8-triaminoanthrachinon als Leuko- derivat unter Zusatz von Borsäure in orga nischen Lösungsmitteln mit p-Aminophenol in Gegenwart von p-Aminophenolchlorhydrat kondensiert,
wobei sehr wahrscheinlich 2 Mol p-Aminophenol mit einem Mol 1-Oxy-4,5,8- triaminoanthrachinon reagieren. Das Konden sationsprodukt löst sich in organischen Lö sungsmitteln mit grüner Farbe und färbt Acetatseide nach geeigneter Verpastung in grünen Tönen von vorzüglicher Echtheit.
<I>Beispiel:</I> 30 Teile reines 1-Oxy-4,5,8-triaminoanthra- chinon werden in 200 Teilen Alkohol mit 40 Teilen p-Aminophenol, 30 Teilen Borsäure, 15 Teilen p-Aminophenolchlorhydrat und 15 Teilen Natriumhydrosulfit zum Kochen er hitzt, bis eine Probe, in Alkohol gelöst, keine weitere Verschiebung der Farbe nach Grün aufweist. Man filtriert kalt, wäscht den Rück stand mit Alkohol und Wasser aus.
Man kann auch Leuko-l-oxy-4, 5, 8-tri- aminoanthrachinon ohne Zusatz von Reduk tionsmitteln zur Kondensation verwenden.
Additional patent to main patent No. 153492. Process for the preparation of a nitrogen-containing anthraquinone derivative. It has been found that a green acetate silk dye is obtained if 1-oxy-4, 5, 8-triaminoanthraquinone is condensed as a leuco derivative with the addition of boric acid in organic solvents with p-aminophenol in the presence of p-aminophenol chlorohydrate,
2 moles of p-aminophenol reacting with one mole of 1-oxy-4,5,8-triaminoanthraquinone very likely. The condensation product dissolves in organic solvents with a green color and, after suitable pasting, dyes acetate silk in green shades of excellent fastness.
<I> Example: </I> 30 parts of pure 1-oxy-4,5,8-triaminoanthraquinone in 200 parts of alcohol with 40 parts of p-aminophenol, 30 parts of boric acid, 15 parts of p-aminophenol chlorohydrate and 15 parts of sodium hydrosulfite to boil it is heated until a sample, dissolved in alcohol, shows no further shift in color to green. It is filtered cold, the residue was washed with alcohol and water.
You can also use leuco-l-oxy-4, 5, 8-tri-aminoanthraquinone without the addition of reducing agents for condensation.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH153492T | 1931-03-25 | ||
| CH158129T | 1931-03-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH158129A true CH158129A (en) | 1932-10-31 |
Family
ID=25716233
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH158129D CH158129A (en) | 1931-03-25 | 1931-03-25 | Process for the preparation of a nitrogenous anthraquinone derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH158129A (en) |
-
1931
- 1931-03-25 CH CH158129D patent/CH158129A/en unknown
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