CH205068A - Process for the preparation of an anthraquinone dye. - Google Patents
Process for the preparation of an anthraquinone dye.Info
- Publication number
- CH205068A CH205068A CH205068DA CH205068A CH 205068 A CH205068 A CH 205068A CH 205068D A CH205068D A CH 205068DA CH 205068 A CH205068 A CH 205068A
- Authority
- CH
- Switzerland
- Prior art keywords
- phenol
- amino
- oetylaniline
- dye
- anthraquinone
- Prior art date
Links
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
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/54—Amino-hydroxy-anthraquinones; Ethers and esters thereof etherified
- C09B1/547—Anthraquinones with aromatic ether groups
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 199190. Verfahren zur Herstellung eines Anthrachinonfarbstoifes. Im Hauptpatent ist ein Verfahren zur Herstellung eines neuen Anthrachinonfarb- stoffes, nämlich 1-Amino-4-p-cetylanilin-2- phenogyanthrachinondisulf o,säure beschrieben. Gemäss, vorliegender Erfindung stellt man denselben:
Farbstoff her, indem man Phenol auf eine 2-Ha1,ogen-,1-amino-4rp-oetyla,nilin- anthrachinehnsulfosäure, wie sie erhalten wer den kann ,durch Sulfonieren von 2-Halogen-l- amino-4-p-cetylanilinanthrachinen mit schwa- chem. Oleum einwirken lässt und die erhaltene Verbindung sulfüniert.
Als 2I-Halogen-l-amino-4-p-cetylanilin- anthrachinonsulfosäure kann, 2,-Brom-1- amino-4-csstylamilinanthrachinonsulfosäure an gewendet werden.
Die Behandlung mit .dem Phenol kann zweekmässigerweise durch Erhitzen mit einem Alkalimetallsalz .des Phenols in einem Über- schusse des Phenols geschehen. Die Sulfonie- rung lässt sich zweckmässigerweise durch Auflösen in 1001%iger Schwefelsäure und Hinzufügen von Oleum bewirken.
Der Farbstoff ist eine violettblaue Sub stanz, welche sich in konzentrierter Schwefel säure mit rötlichvioletter Farbe löst und mit Wasser klare blaue Lösungen ;gibt, die leicht schäumen. Der Farbstoff erzeugt auf Wolle lebhaft rötlichblaue Töne, welche sehr gute Walk- und Lichtechtheit aufweisen und intensivem. Waschen sehr guL, widerstehen.
Beispiel: 70 Teile 2.-Brom-l-amino-4-p-cetylanilin- anthTachinonsulfosäure (als Natriumsalz), wie sie gemäss. Beispiel 1 der britischen Pa tentschrift Nr.
443,776, unter Anwendung von p-Cetylanilin anstatt p-D'o,decylanilin, und nachfolgende Sulfonierang mit schwachem Oleum, erhalten werden kann, 10 Teile ge- pulvertes Ätznatron und '350 Teile Phenol werden,
zusammen 6 Stunden lang auf 170 bis 176' C erhitzt. Das Reaktionsgemiscb wird mit 80 C in 260 Teile 5 % ige Natron lauge gegossen, die ausgefällte Phenoxy- verbindung abfiltriert, mit kaltem Wasser gewaschen und bei<B>80'</B> C getrocknet.
50 Teile der so erhaltenen 1-Amino-4-p- cetylanilin-2 -phenoxyanthrachinonsulfosäure löst man bei 15-.2.0 C in 500 Teilen 100%iger Schwefelsäure und fügt 1.0 Teile 20 % iges Oleum hinzu. Nach einigen Minuten wird -da.s Sulfonierungsgemisch in 2000 Teile Eiswasser gegossen, das Produkt abfiltriert, der Filterkuchen in<B>300</B> Teilen Wasser gelöst und diese Lösung mit Soda neutralisiert.
Man fällt hierauf den Farbstoff bei 70 C mit 300 Teilen Kochsalz aus, filtriert ab und trocknet bei 80 C.
Additional patent to the main patent no. 199190. Process for the production of an anthraquinone dye. The main patent describes a process for the production of a new anthraquinone dye, namely 1-amino-4-p-cetylaniline-2-phenogyanthraquinone disulfo, acid. According to the present invention, the same is made:
Dye produced by phenol on a 2-Ha1, ogen-, 1-amino-4rp-oetyla, niline anthraquinone sulfonic acid, as it can be obtained by sulfonating 2-halo-1-amino-4-p-cetylaniline anthraquinones with weak. Let oleum act and the compound obtained sulfeniert.
As 2I-halo-1-amino-4-p-cetylaniline-anthraquinone sulfonic acid, 2, -Bromo-1-amino-4-csstylamilinanthraquinone sulfonic acid can be used.
The treatment with the phenol can take place in two ways by heating with an alkali metal salt of the phenol in an excess of the phenol. The sulfonation can conveniently be brought about by dissolving in 1001% sulfuric acid and adding oleum.
The dye is a violet-blue substance that dissolves in concentrated sulfuric acid with a reddish-violet color and, when mixed with water, gives clear blue solutions that foam slightly. The dye produces lively reddish-blue tones on wool, which are very fast and lightfast and are intense. Wash very well, resist.
Example: 70 parts of 2.-bromo-1-amino-4-p-cetylaniline-anth-tachinone sulfonic acid (as sodium salt), as described in. Example 1 of British Patent No.
443,776, using p-cetylaniline instead of p-D'o, decylaniline, and subsequent sulfonation with weak oleum, can be obtained, 10 parts of powdered caustic soda and 350 parts of phenol,
heated together for 6 hours to 170 to 176 ° C. The reaction mixture is poured at 80 ° C. into 260 parts of 5% sodium hydroxide solution, the precipitated phenoxy compound is filtered off, washed with cold water and dried at 80 ° C.
50 parts of the 1-amino-4-p-cetylaniline-2-phenoxyanthraquinone sulfonic acid obtained in this way are dissolved in 500 parts of 100% sulfuric acid at 15-2.0 C and 1.0 part of 20% oleum is added. After a few minutes, the sulfonation mixture is poured into 2000 parts of ice water, the product is filtered off, the filter cake is dissolved in 300 parts of water and this solution is neutralized with soda.
The dye is then precipitated at 70 ° C. with 300 parts of sodium chloride, filtered off and dried at 80 ° C.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB205068X | 1936-07-01 | ||
CH199190T | 1937-06-14 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH205068A true CH205068A (en) | 1939-05-31 |
Family
ID=25723231
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH205068D CH205068A (en) | 1936-07-01 | 1937-06-14 | Process for the preparation of an anthraquinone dye. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH205068A (en) |
-
1937
- 1937-06-14 CH CH205068D patent/CH205068A/en unknown
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