DE585528C - Process for the preparation of 1,4-diamino-2-aryloxyanthraquinone-3-sulfonic acids - Google Patents

Process for the preparation of 1,4-diamino-2-aryloxyanthraquinone-3-sulfonic acids

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Publication number
DE585528C
DE585528C DEI44013D DEI0044013D DE585528C DE 585528 C DE585528 C DE 585528C DE I44013 D DEI44013 D DE I44013D DE I0044013 D DEI0044013 D DE I0044013D DE 585528 C DE585528 C DE 585528C
Authority
DE
Germany
Prior art keywords
diamino
aryloxyanthraquinone
sulfonic acids
halogenanthraquinones
preparation
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
DEI44013D
Other languages
German (de)
Inventor
Dr Fritz Baumann
Dr Bertold Stein
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to DEI44013D priority Critical patent/DE585528C/en
Application granted granted Critical
Publication of DE585528C publication Critical patent/DE585528C/en
Expired legal-status Critical Current

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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
    • C09B1/22—Dyes with unsubstituted amino groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Es wurde gefunden, daß man die 1,- 4-D1-amino-2-aryloxyanthrachinon-3-sulfonsäuren in bester Ausbeute und Reinheit'in der Weise erhalten kann, daß man'1, 4-Diamino-2-aryl-It has been found that the 1,4-D1-amino-2-aryloxyanthraquinone-3-sulfonic acids in the best yield and purity 'can be obtained in such a way that one'1, 4-diamino-2-aryl-

. 5 oxy-3-halogenanthrachinone in Gegenwart von . Wasser und gegebenenfalls eines organischen Lösungsmittels und unter Erwärmen der Reaktionsmischung mit neutralen-Sulfiten bei erhöhtem Druck umsetzt. Die als Ausgangs-. 5 oxy-3-halogenanthraquinones in the presence of. Water and optionally an organic one Solvent and while heating the reaction mixture with neutral sulfites increased pressure. The starting point

xo material verwendeten i, 4-Diamino-2-aryloxy-3-halogenanthrachinone, können leicht durch Umsetzung von 1, 4-Diamino-2, 3-dihalogenanthrachinonen mit aromatischen Oxyverbindungen wie Phenolen oder Naphthole^xo material used i, 4-diamino-2-aryloxy-3-halogenanthraquinones, can easily by reacting 1, 4-diamino-2, 3-dihalogenanthraquinones with aromatic oxy compounds such as phenols or naphthols ^

zweckmäßig in Gegen wart, eines säurebindenden Mittels gewonnen werden. Erfindungsgemäß ist es nicht. notwendig, die so hergestellten i,^-Diaminoaryloxy-s-halogenanthrachinone vor der Umsetzung mit neutralen SuI-fiten zu isolieren; man kann vielmehr auch so vorgehen, daß man der Reaktionsmischung, welche die I, ^-Diamino^-aryloxy-s-halogenanthrachinone enthält, eine wäßrige Lösung eines neutralen Sulfits zusetzt und dann erv 25 wärmt.expediently in the presence of an acid-binding agent can be obtained. According to the invention is not it. necessary, the so produced i, ^ - Diaminoaryloxy-s-halogenanthraquinones to isolate prior to implementation with neutral suI-fites; rather, one can also do so proceed that one of the reaction mixture, which the I, ^ -Diamino ^ -aryloxy-s-halogenanthraquinones contains, an aqueous solution of a neutral sulfite is added and then erv 25 warms.

Beispieli-Example-

10 Gewichtsteile 1, 4-Diamino-'2-phenoxy-3-chloranthrachinon, 60 Gewichtsteile Phenol, 150 Gewichtsteile Wasser und 25 Gewichtsteile kristallisiertes Natriumsulfit werden in einem Druckgefäß 5 bis 6 Stunden auf 1400 erhitzt. Alsdann wird das Phenol mit Wasserdampf apgestilliert und die 1,4-D1-amino - 2 - phenoxyanthrachinon - 3 - sulf onsäure mit Kochsalz ausgesalzen. Der Farbstoff färbt Wolle in sehr klaren echten violetten Tönen. Aus I, 4-Diamino-2-phenoxy-3-bromanthrachinon entsteht in ähnlicher Weise dieselbe SuIfonsäure.10 parts by weight of 1, 4-diamino-'2-phenoxy-3-chloroanthraquinone, 60 parts by weight of phenol, 150 parts by weight of water and 25 weight parts of crystalline sodium sulfite is heated in a pressure vessel 5 to 6 hours at 140 0th The phenol is then distilled off with steam and the 1,4-D1-amino-2-phenoxyanthraquinone-3-sulfonic acid is salted out with common salt. The dye dyes wool in very clear, real purple tones. The same sulfonic acid is formed in a similar manner from 1,4-diamino-2-phenoxy-3-bromoanthraquinone.

Beispiel 2Example 2

15,4 Gewichtsteile 1, 4-Diamino-2, 3-dichloranthrachinon, 90 Gewichtsteile Phenol und 7, 5 Gewichtsteile fein gemahlene Pottasche erwärmt man in einem offenen Autoklaven auf 150 bis i6o°, bis eine aufgearbeitete Probe in. 5°/oigem Oleum bei Zimmertemperatur glatt sulfonierbar ist, was im allgemeinen nach 5 bis 7 Stunden der Fall ist. Nach restloser Umsetzung des Ausgangsmaterials kühlt man auf etwa ioo° ab, läßt 32 Gewichtsteile Natriumsulfit, in 250 Gewichtsteilen Wasser gelöst, einlaufen und erwärmt dann im geschlossenen Gefäß auf 140 bis i4S°. Man unterbricht die Reaktion, sobald eine aufgearbeitete Probe halogenfrei ist. Die Aufarbeitung des fertigen Farbstoffs erfolgt in üblicher Weise. """"^^»-w,,, 15.4 parts by weight of 1, 4-diamino-2, dichloroanthraquinone 3, 90 parts by weight of phenol and 7, 5 parts by weight of finely ground potassium carbonate are heated in an open autoclave at 150 to I6O ° until a worked-up sample. 5 ° / o sodium Oleum can be sulfonated smoothly at room temperature, which is generally the case after 5 to 7 hours. After the starting material has reacted completely, the mixture is cooled to about 100 °, 32 parts by weight of sodium sulfite dissolved in 250 parts by weight of water are allowed to run in and then heated to 140 ° to 14 ° in a closed vessel. The reaction is interrupted as soon as a processed sample is halogen-free. The finished dye is worked up in the customary manner. """" ^^ »- w ,,,

Aus der franz. Patentschrift 718 505 iStTeTf Verfahren zur Herstellung von 1, 4-Diamino-2-aryloxy-3-sulfonsäuren bekanntgeworden,From the French Patent 718 505 iStTeTf Process for the preparation of 1,4-diamino-2-aryloxy-3-sulfonic acids known,

*) Von dgm Patentsucher sind als die Erfinder angegeben worden:*) The inventors have been named by dgm patent searchers: Dr. Fritz Naumann in Leverkusen und Dr. Bertold Stein in Ludwigshafen.Dr. Fritz Naumann in Leverkusen and Dr. Bertold Stein in Ludwigshafen.

welches darin besteht, daß man ι, 4-Diamino-2, 3-dihalogerianthrachinGne rnit Phenolen und Salzen der schwefligen Säure in Gegenwart von Wasserin der Wärme "behandelt. Diesem Verfahren gegenüber weist das vorliegende den Vorteil auf, daß es glatter verläuft und insbesondere die Endprodukte in größerer Reinheit, besserer Ausbeute und ohne gleichzeitige Bildung unerwünschter Nebenprodukte liefert.which consists in that one ι, 4-diamino-2, 3-dihalogerianthraquinine with phenols and Salts of sulphurous acid in the presence of water in the heat "treated. This Compared to the method, the present invention has the advantage that it is smoother and especially the end products in greater purity, better yield and without the simultaneous formation of undesired by-products.

Claims (2)

PAtentansprü-che :Patent claims: ι. Verfahren zur Herstellung von 1,4-ι. Process for the production of 1,4- -Diamino-2-aryloxyanthrachinon·· 3-sulf onsäuren, dadurch gekennzeichnet, daß man i, 4-Diamino-2-aryloxy-3-halogenanthrachinone mit neutralen Sulfiten in Gegenwart von Wasser und gegebenenfalls eines organischen Lösungsmittels in der Wärme unter erhöhtem Druck behandelt.-Diamino-2-aryloxyanthraquinone 3-sulfonic acids, characterized in that i, 4-diamino-2-aryloxy-3-halogenanthraquinones with neutral sulfites in the presence of water and optionally an organic solvent in the Treated heat under increased pressure. 2. Ausführungsform des Verfahrens nach Anspruch 1, dadurch gekennzeichnet, daß man zunächst 1, 4-Diamino-2-aryloxy-3-halogenanthrachinone durch Umsetzung von i, 4 - Diamino - 2,3 - dihalogenanthrachinonen mit aromatischen Oxyverbindungen herstellt, dann, ohne das Reaktionsprodukt zu isolieren,- der Reaktionsmischung eine wäßrige Lösung eines neutralen Sulfits zusetzt und schließlich die Reaktionsmischung unter erhöhtem Druck erwärmt.2. Embodiment of the method according to claim 1, characterized in that that you first 1, 4-diamino-2-aryloxy-3-halogenanthraquinones by reacting i, 4 - diamino - 2,3 - dihaloanthraquinones with aromatic oxy compounds, then, without isolating the reaction product, - the reaction mixture an aqueous solution of a neutral Sulphite is added and finally the reaction mixture under increased pressure warmed up.
DEI44013D 1932-03-15 1932-03-16 Process for the preparation of 1,4-diamino-2-aryloxyanthraquinone-3-sulfonic acids Expired DE585528C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEI44013D DE585528C (en) 1932-03-15 1932-03-16 Process for the preparation of 1,4-diamino-2-aryloxyanthraquinone-3-sulfonic acids

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE416433X 1932-03-15
DEI44013D DE585528C (en) 1932-03-15 1932-03-16 Process for the preparation of 1,4-diamino-2-aryloxyanthraquinone-3-sulfonic acids

Publications (1)

Publication Number Publication Date
DE585528C true DE585528C (en) 1933-10-04

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ID=25910693

Family Applications (1)

Application Number Title Priority Date Filing Date
DEI44013D Expired DE585528C (en) 1932-03-15 1932-03-16 Process for the preparation of 1,4-diamino-2-aryloxyanthraquinone-3-sulfonic acids

Country Status (1)

Country Link
DE (1) DE585528C (en)

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