DE632753C - Process for the preparation of anthraquinone dyes - Google Patents

Process for the preparation of anthraquinone dyes

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Publication number
DE632753C
DE632753C DEI50575D DEI0050575D DE632753C DE 632753 C DE632753 C DE 632753C DE I50575 D DEI50575 D DE I50575D DE I0050575 D DEI0050575 D DE I0050575D DE 632753 C DE632753 C DE 632753C
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DE
Germany
Prior art keywords
weight
parts
blue
water
amino
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
DEI50575D
Other languages
German (de)
Inventor
Dr Curt Bamberger
Dr Claus Weinand
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 DEI50575D priority Critical patent/DE632753C/en
Application granted granted Critical
Publication of DE632753C publication Critical patent/DE632753C/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
    • C09B1/16—Amino-anthraquinones
    • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
    • C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
    • C09B1/28—Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups
    • C09B1/30—Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups sulfonated
    • 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
    • C09B1/202—Preparation from starting materials already containing the anthracene nucleus sulfonated
    • C09B1/203—Preparation from starting materials already containing the anthracene nucleus sulfonated only sulfonated in the anthracene nucleus
    • 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
    • C09B1/264—Dyes with amino groups substituted by hydrocarbon radicals sulfonated
    • C09B1/266—Dyes with amino groups substituted by hydrocarbon radicals sulfonated only sulfonated in the anthracene nucleus

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)

Description

Verfahren zur Herstellung von Anthrachinonfarbstoffen Es wurde gefunden, daß wertvolle saure Wollfarbstoffe erhalten werden, wenn man auf i-Amino-q.-halogenanthrachinon-2-sulfonsäuren, die im anderen Kern eine Sulfonamidgruppe enthalten, Amine einwirken läßt. Die Produkte stellen saure Wollfarbstoffe dar und zeichnen sich gegenüber den entsprechenden Farbstoffen, welche keine Sulfonamidgruppe enthalten, dadurch aus, daß die Nuance erheblich nach grün verschoben ist. Die neuen Farbstoffe stellen in der Regel blaue bis blaugrüne Produkte dar, die sich in Wasser mit lebhaftblauer bis blaugrüner Farbe lösen und Wolle aus saurem Bade in diesen Nuancen von leervorragender Lichtechtheit anfärben. Die Farbstoffe sind 'besonders durch ein hervorragendes Egalisiervermögen ausgezeichnet.Process for the production of anthraquinone dyes It has been found that valuable acidic wool dyes are obtained if one uses i-amino-q.-halogenanthraquinone-2-sulfonic acids, which contain a sulfonamide group in the other nucleus, allows amines to act. The products represent acidic wool dyes and stand out from the corresponding Dyes, which do not contain a sulfonamide group, are characterized by the fact that the nuance shifted significantly to green. The new dyes are usually blue to blue-green products that change in water with vivid blue to blue-green Dissolve color and wool from acid baths in these nuances of outstanding lightfastness stain. The dyes are 'special because of their excellent leveling power excellent.

Die Reaktion kann in üblicher Weise z. B. in Gegenwart von Kupfersalzen als Katalysatoren durchgeführt werden. Die Wasserstoffatome der Sulfonamidgruppe können durch Alkyl-, Aryl- oder Hydroarylreste ganz oder teilweise substituiert sein.The reaction can be carried out in a conventional manner, for. B. in the presence of copper salts be carried out as catalysts. The hydrogen atoms of the sulfonamide group can be completely or partially substituted by alkyl, aryl or hydroaryl radicals be.

Beispiel i io Gewichtsteile i-Amino-q.-brom-6-(dimethyl) - sulfonamidanthrachinon - 2 - sulfonsäure ,,verden mit 3o Gewichtsteilen Hexahydroanilin in Gegenwart von q.5o Gewichtsteilen Wasser, 5o Gewichtsteilen Alkohol unter Zugabe von 6 Gewichtsteilen Soda und o,5 Gewichtsteilen Kupfersulfat 2 Stunden gekocht. Alkohol und das überschüssige Hexahydroanilin werden durch Einblasen von Wasserdampf abgetrieben. Aus der verbleibenden Lösung wird der entstandene Farbstoff durch Zugabe von Kochsalz ausgesalzen. Er stellt blaue Nadeln dar, die sich in Wasser mit klarer, grünstichigblauer Farbe lösen und Wolle aus saurem Bade mit grünstichigblauer Nuance von hervorragender Lichtechtheit anfärben.Example 10 parts by weight of i-amino-q.-bromo-6- (dimethyl) sulfonamidanthraquinone - 2 - sulfonic acid ,, verden with 3o parts by weight of hexahydroaniline in the presence of q.50 parts by weight of water, 50 parts by weight of alcohol with the addition of 6 parts by weight Soda and 0.5 parts by weight of copper sulfate boiled for 2 hours. Alcohol and the excess Hexahydroaniline are driven off by blowing in steam. From the remaining Solution, the resulting dye is salted out by adding sodium chloride. He represents blue needles that are clear, greenish blue in color in water solve and wool from an acid bath with a greenish blue shade of excellent Dye lightfastness.

Beispiel 2 io Gewichtsteile i-Amino-q.-brom-6-(dimethyl) - sulfonamidanthrachinon - 2 - sulfonsäure werden mit 8 Gewichtsteilen p-Aminoacetanilid unter Zugabe von io Gewichtsteilen Natriumbicarbonat und o,5 Gewichtsteilen Kupferchlorür in ioo Gewichtsteilen Wasser ¢ bis 6 Stunden bei 6o bis 8o° C erhitzt. Nach dem Erkalten wird der entstandene Farbstoff abgesaugt und aus Wasser umgelöst. Er stellt blaugrüne Nadeln dar, die sich in Wasser mit blaugrüner Farbe lösen und Wolle aus saurem Bade in sehr echten blaugrünen Nuancen anfärben.Example 2 10 parts by weight of i-amino-q.-bromo-6- (dimethyl) sulfonamidanthraquinone - 2 - sulfonic acid with 8 parts by weight of p-aminoacetanilide with the addition of 10 parts by weight of sodium bicarbonate and 0.5 parts by weight of copper chloride in 100 Parts by weight of water [heated at 6o to 8o ° C for up to 6 hours. After cooling down the resulting dye is sucked off and redissolved in water. He puts blue-green They represent needles that dissolve in water with a blue-green color, and wool from an acid bath Color in very real blue-green shades.

Beispiel 3 io Gewichtsteile i-amino-q.-brom-6-sulfondiäthylamidoanthrachinon-2-sulfonsaures Natrium, 3oo Gewichtsteile Methylaminlösung io%ig, 5 Gewichtsteile Natriumcarbonat und 0,5 Gewichtsteile Kupfersulfat werden 2 Stun- den auf dem Wasserbad erwärmt. Die an- fangs rote Lösung wird ällmählich grünstichig- blau. Nachdem das überschüssige Meth 1=; amin mit Wasserdampf abgetrieben wordizi- ist, wird die entstandene i-Amino-¢-methyl=" amino-6-sulfondiäthylaminoanthrachinon-2-sul- sonsäure mit Kochsalz in kristalliner Form abgeschieden. Sie löst sich in Wasser mit lebhaftblauer Farbe und färbt Wolle aus saurem Bade in klaren blauen Tönen an. Beispiel q. 5 Gewichtsteile i-amino-4.-brom-7-sulfonme- thylamidoanthrachinon-2-sulfonsaures Natrium werden mit 20 Gewichtsteilen Anilin unter Zusatz von 5 Gewichtsteilen Natriumcarbonat und .o,3 Gewichtsteilen Kupfersulfat in ioo Gewichtsteilen Wasser il-/2 Stunde unter Rühren zum Sieden erhitzt. Beim Erkalten scheidet sich der entstandene Farbstoff - i-Aminoi,-änilido - 7 - sulfonmethyiamidoanthrachinon-2-sulfonsäure - in Nadeln ab. Sie lösen -.si"ch in Wasser mit blauer Farbe und färben .Wolle aus saurem Bade in grünstichigblauen Tönen an.Example 3 10 parts by weight of i-amino-q.-bromo-6-sulfone diethylamidoanthraquinone-2-sulfonic acid sodium, 300 parts by weight of methylamine solution 10% strength, 5 parts by weight of sodium carbonate and 0.5 parts by weight of copper sulphate are used for 2 hours heated on the water bath. The other The red solution gradually turns green. blue. After the excess meth 1 =; amine expelled with water vapor wordizi- is, the resulting i-amino- ¢ -methyl = " amino-6-sulfone diethylaminoanthraquinone-2-sul- Acid with common salt in crystalline form deposited. It dissolves in water with vivid blue color and dyes wool acidic baths in clear blue tones. Example q. 5 parts by weight of i-amino-4.-bromo-7-sulfonme- thylamidoanthraquinone-2-sulfonic acid sodium are with 20 parts by weight of aniline under Addition of 5 parts by weight of sodium carbonate and .o, 3 parts by weight of copper sulfate in 100 parts by weight of water heated to boiling for 2 hours with stirring. When cooling down, the resulting dye - i-aminoi, -anilido - 7 - sulfonmethyiamidoanthraquinone-2-sulfonic acid - separates in needles. They dissolve in water with a blue color and dye wool from an acid bath in greenish blue tones.

Claims (1)

PATENTANSPRUCH Verfahren zur Herstellung von Anthrachinonfarbstoffen, dadurch gekennzeichnet, daß man auf i-Amino-q.-halogenanthrachinon-2-sulfonsäuren, die im anderen Kern eine Sulfonamidgruppe enthalten, Amine einwirken läßt.PATENT CLAIM Process for the production of anthraquinone dyes, characterized in that i-amino-q.-halogenanthraquinone-2-sulfonic acids, which contain a sulfonamide group in the other nucleus, allows amines to act.
DEI50575D 1934-09-14 1934-09-15 Process for the preparation of anthraquinone dyes Expired DE632753C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEI50575D DE632753C (en) 1934-09-14 1934-09-15 Process for the preparation of anthraquinone dyes

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2067469X 1934-09-14
DEI50575D DE632753C (en) 1934-09-14 1934-09-15 Process for the preparation of anthraquinone dyes

Publications (1)

Publication Number Publication Date
DE632753C true DE632753C (en) 1936-07-13

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Application Number Title Priority Date Filing Date
DEI50575D Expired DE632753C (en) 1934-09-14 1934-09-15 Process for the preparation of anthraquinone dyes

Country Status (1)

Country Link
DE (1) DE632753C (en)

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