DE1059133B - Process for the production of gray sulfur dyes of the phthalocyanine series - Google Patents

Process for the production of gray sulfur dyes of the phthalocyanine series

Info

Publication number
DE1059133B
DE1059133B DEC14771A DEC0014771A DE1059133B DE 1059133 B DE1059133 B DE 1059133B DE C14771 A DEC14771 A DE C14771A DE C0014771 A DEC0014771 A DE C0014771A DE 1059133 B DE1059133 B DE 1059133B
Authority
DE
Germany
Prior art keywords
production
hydroxylamine
gray
sulfur dyes
phthalocyanine
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.)
Pending
Application number
DEC14771A
Other languages
German (de)
Inventor
Dr Werner Zerweck
Dr Heinrich Ritter
Dr Eberhard Stier
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.)
Cassella Farbwerke Mainkur AG
Original Assignee
Cassella Farbwerke Mainkur 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 Cassella Farbwerke Mainkur AG filed Critical Cassella Farbwerke Mainkur AG
Priority to DEC14771A priority Critical patent/DE1059133B/en
Publication of DE1059133B publication Critical patent/DE1059133B/en
Pending legal-status Critical Current

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
    • C09B49/00—Sulfur dyes
    • C09B49/12—Sulfur dyes from other compounds, e.g. other heterocyclic compounds
    • C09B49/122—Sulfur dyes from other compounds, e.g. other heterocyclic compounds from phthalocyanine compounds
    • 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
    • C09B47/00—Porphines; Azaporphines
    • C09B47/04—Phthalocyanines abbreviation: Pc
    • C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex

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

Description

Verfahren zur Herstellung von grauen Schwefelfarbstoffen der Phthalocyaninreihe Zusatz zum Patent 947 409 Gegenstand des deutschen Patentes 947 409 ist ein Verfahren zur Herstellung von grauen Schwefelfarbstoffen der Phthalocyaninreihe, das dadurch gekennzeichnet ist, daß man auf Phthalocyanine oder deren Komplexsalze bei einer Temperatur von etwa 100 bis 150° C Hydroxylamin bzw. Hydroxylamin liefernde Substanzen und Chlorsulfonsäure in Gegenwart von Verbindungen der Elemente der V. und VI. Gruppe des Periodischen Systems einwirken läßt und die so erhaltenen Produkte mit Reduktionsmitteln behandelt.Process for the production of gray sulfur dyes of the phthalocyanine series Addition to patent 947 409 The subject of German patent 947 409 is a method for the production of gray sulfur dyes of the phthalocyanine series, which thereby is characterized in that one on phthalocyanines or their complex salts in a Temperature of about 100 to 150 ° C hydroxylamine or hydroxylamine-supplying substances and chlorosulfonic acid in the presence of compounds of the elements of V. and VI. group of the Periodic Table and the products thus obtained with reducing agents treated.

Es wurde nun gefunden, daß man Farbstoffe von erheblich höherer Farbstärke, besserer Waschechtheit und besserem Ziehvermögen erhält, wenn man im Anschluß an die Umsetzung mit Hydroxylamin vor der Behandlung mit Reduktionsmitteln gemäß Patentschrift 9'47 409 das Reaktionsgemisch mit mindestens 5 Mol Chlorschwefel, bezogen auf Phthalocyanin, behandelt.It has now been found that dyes of considerably higher color strength, better wash fastness and better drawability if you follow the reaction with hydroxylamine before treatment with reducing agents according to the patent 9'47 409 the reaction mixture with at least 5 moles of chlorosulfur, based on phthalocyanine, treated.

Die so erhaltenen Produkte liefern zumeist graue bis olivgraue Farbtöne. Die Färbungen zeichnen sich durch gute Echtheitseigenschaften, insbesondere durch sehr gute Lichtechheit, aus.The products obtained in this way mostly deliver gray to olive-gray shades. The dyeings are distinguished by good fastness properties, in particular by very good lightfastness, off.

Beispiel 23 Teile Kupferphthalocyanin, 15,6 Teile 9'5%iges Hydroxylaminsulfat und 0,11 Teile Ammoniummolybdat werden in 345 Teilen Chlorsulfonsäure 2 Stunden bei 125° C gerührt. Bei gleicher Temperatur läßt man innerhalb 10 bis 20 Minuten 54 Teile Chlorschwefel eintropfen und rührt nochmals 1 bis 2 Stunden bei 125' C. Der Ansatz wird auf ein Gemisch von 690 Teilen Eis, 500' Teilen roher konzentrierter Salzsäure und 54 Teilen Eisenpulver gegossen. Nach mehrstündigem Rühren bei 50' C wird der Farbstoff in bekannter Weise isoliert. Das Produkt färbt die Textilfaser aus violettstichig schwarzgrauer Schwefelnatriumlösunggrünstickig olivgrau. Die Färbungen besitzen gute Wasch- und sehr gute Lichtechtheit.Example 23 parts of copper phthalocyanine, 15.6 parts of 9.5% strength hydroxylamine sulfate and 0.11 part of ammonium molybdate are in 345 parts of chlorosulfonic acid for 2 hours stirred at 125 ° C. The mixture is left at the same temperature for 10 to 20 minutes Drop in 54 parts of chlorosulfur and stir again for 1 to 2 hours at 125 ° C. The batch is concentrated to a mixture of 690 parts of ice, 500 parts of crude Hydrochloric acid and 54 parts of iron powder poured. After stirring for several hours at 50 ' C the dye is isolated in a known manner. The product colors the textile fiber from violet-tinged black-gray sulphurous sodium solution green-tinged olive-gray. the Dyeings have good washfastness and very good lightfastness.

Verringert man die Menge des Chlorschwefels auf 40,5 bzw. 27 Teile, so. erhält man Farbstoffe mit nahezu gleichen Eigenschaften. Vergrößert man die Menge des Hydroxylaminsulfates von 15,6 auf 17,5 Teile, so entsteht ein Produkt, das sich von dem obenerwähnten nur in sehr geringem Maße unterscheidet.If you reduce the amount of chlorosulfur to 40.5 or 27 parts, so. you get dyes with almost the same properties. If you enlarge the Amount of hydroxylamine sulfate from 15.6 to 17.5 parts, the result is a product which differs only slightly from the above mentioned.

Claims (1)

PATENTANSPRUCH: Abänderung des Verfahrens des Hauptpatentes 947 409 zur Herstellung von grauen Schwefelfarbstoffen der Phthalocyaninreihe durch Einwirkung von Hydroxylamin bzw. Hydroxylamin liefernden Substanzen und von Chlorsulfonsäure auf Phthalocyanine und deren Komplexsalze in Gegenwart von Verbindungen der Elemente, der V. und VI. Gruppe des Periodischen Systems und Behandlung der erhaltenen Produkte mit Reduktionsmitteln, dadurch gekennzeichnet, daß man hier im Anschluß an die Umsetzung mit Hydroxylamin vor der Behandlung mit Reduktionsmitteln das Reaktionsgemisch mit mindestens 5 Mol Chlorschwefel, bezogen auf Phthalocyanin, behandelt. Bei der Bekanntmachung der Anmeldung sind 2 Färbtafeln ausgelegt worden.PATENT CLAIM: Modification of the process of main patent 947 409 for the production of gray sulfur dyes of the phthalocyanine series by action of hydroxylamine or hydroxylamine-supplying substances and of chlorosulfonic acid on phthalocyanines and their complex salts in the presence of compounds of the elements, the V. and VI. Group of the periodic table and treatment of the products obtained with reducing agents, characterized in that this is followed by the reaction with hydroxylamine before treatment with reducing agents with the reaction mixture treated at least 5 moles of chlorosulfur, based on phthalocyanine. At the notice 2 color tables have been laid out for the application.
DEC14771A 1957-05-02 1957-05-02 Process for the production of gray sulfur dyes of the phthalocyanine series Pending DE1059133B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEC14771A DE1059133B (en) 1957-05-02 1957-05-02 Process for the production of gray sulfur dyes of the phthalocyanine series

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEC14771A DE1059133B (en) 1957-05-02 1957-05-02 Process for the production of gray sulfur dyes of the phthalocyanine series

Publications (1)

Publication Number Publication Date
DE1059133B true DE1059133B (en) 1959-06-11

Family

ID=7015722

Family Applications (1)

Application Number Title Priority Date Filing Date
DEC14771A Pending DE1059133B (en) 1957-05-02 1957-05-02 Process for the production of gray sulfur dyes of the phthalocyanine series

Country Status (1)

Country Link
DE (1) DE1059133B (en)

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