DE1176775B - Process for the production of dyes - Google Patents

Process for the production of dyes

Info

Publication number
DE1176775B
DE1176775B DEC24778A DEC0024778A DE1176775B DE 1176775 B DE1176775 B DE 1176775B DE C24778 A DEC24778 A DE C24778A DE C0024778 A DEC0024778 A DE C0024778A DE 1176775 B DE1176775 B DE 1176775B
Authority
DE
Germany
Prior art keywords
dyes
oxy
production
anthraquinone
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.)
Pending
Application number
DEC24778A
Other languages
German (de)
Inventor
Dr Werner Zerweck
Dr Ernst Heinrich
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 DEC24778A priority Critical patent/DE1176775B/en
Publication of DE1176775B publication Critical patent/DE1176775B/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
    • C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
    • C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
    • C09B5/34—Anthraquinone acridones or thioxanthrones
    • C09B5/347—Anthraquinone acridones

Landscapes

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

Description

Verfahren zur Herstellung von Farbstoffen Es wurde gefunden, daß man wertvolle Polyesterfasern echt färbende Farbstoffe erhält, wenn man 1 - Amino - anthrachinon - 3,4(N) - benzacridon mit 3-Oxy-4-halogen-benzoesäuren oder den funktionellen Derivaten dieser Säuren kondensiert.Process for the preparation of dyestuffs It has been found that valuable polyester fibers are obtained with fast coloring dyestuffs if 1 - amino - anthraquinone - 3,4 (N) - benzacridone with 3-oxy-4-halo-benzoic acids or the functional derivatives of these acids are used condensed.

Die neuen Farbstoffe entsprechen der allgemeinen Formel worin X ein Halogenatom bedeutet.The new dyes correspond to the general formula wherein X represents a halogen atom.

Diese Farbstoffe ergeben farbstarke Drucke bzw. Färbungen auf Polyesterfaserinaterialien mit sehr guten Echtheitseigenschaften, insbesondere hervorragender Lichtechtheit.These dyes produce strong prints or dyeings on polyester fiber materials with very good fastness properties, in particular excellent light fastness.

Die erfindungsgemäß herstellbaren Farbstoffe besitzen beim Drucken auf Polyestergewebe eine größere Farbstärke als der aus der USA.-Patentschrift 2 568 966, Beispiel 3, bekannte Farbstoff, der durch Acylierung von 1 -Amino-anthrachinon-3,4(N)-benzacridon mit 3,4-Dichlorbenzoesäure erhalten wird. When printed on polyester fabric, the dyes which can be prepared according to the invention have a greater color strength than the dye known from US Pat. No. 2,568,966, Example 3, which is obtained by acylating 1- amino-anthraquinone-3,4 (N) -benzacridone with 3 , 4-dichlorobenzoic acid is obtained.

B e i s p i e 1 Ein Gemisch aus 300 Teilen Monochlorbenzol, 32,6 Teilen 3-Oxy-4-brombenzoesäure und 19,0 Teilen Thionylchlorid wird je 2 Stunden auf 80, 90 und 100'C erwärmt. Anschließend wird die Reaktionslösung mit 34,0 Teilen 1-Amino-anthrachinon-3,4(N)-benzacridon versetzt und 12 Stunden auf 120'C erhitzt. Nach dem Erkalten wird der entstandene Farbstoff abgesaugt und zunächst mit Monochlorbenzol, dann mit Methanol ausgewaschen und getrocknet. Das dunkelblaue Farbstoffpulver löst sich mit rotoranger Farbe in konzentrierter Schwefelsäure. Der Farbstoff liefert auf Polyesterfasern farbstarke, klare, grünstichig blaue Färbungen bzw. Drucke von hervorragenden Echtheitseigenschaften.B ice p e 1 A mixture of 300 parts of monochlorobenzene, 32.6 parts of 3-oxy-4-bromobenzoic acid and 19.0 parts of thionyl chloride is 2 hours each at 80, 90 and heated 100'C. The reaction solution is then mixed with 34.0 parts of 1-amino-anthraquinone-3,4 (N) -benzacridone and heated to 120.degree. C. for 12 hours. After cooling, the resulting dye is filtered off with suction and washed first with monochlorobenzene and then with methanol and dried. The dark blue dye powder dissolves in concentrated sulfuric acid with a red-orange color. The dye gives strong, clear, greenish blue dyeings or prints with excellent fastness properties on polyester fibers.

Ein Farbstoff, der auf Polyesterfasern Färbungen und Drucke von ähnlicher Nuance und ähnlichen Echtheitseigenschaften ergibt, wird erhalten, wenn in dem obigen Beispiel die 3-Oxy-4-brombenzoesäure ersetzt wird durch eine äquimolekulare Menge von 3-Oxy-4-chlor-benzoesäure.A dye that resembles dyeings and prints on polyester fibers Nuance and similar fastness properties is obtained when in the above Example the 3-oxy-4-bromobenzoic acid is replaced by an equimolecular amount of 3-oxy-4-chloro-benzoic acid.

Claims (1)

Patentanspruch: Verfahren zur Herstellung von Farbstoffen der allgemeinen Formel worin X ein Halogenatom bedeutet, d a d u r c h gekennzeichnet, daß man 1-Amino-anthrachinon-3,4(N)-benzacridon mit 3-Oxy-4-halogenbenzoesäuren oder den funktionellen Derivaten dieser Säuren kondensiert. In Betracht gezogene Druckschriften: USA.-Patentschrift Nr. 2 568 966, Beispiel 3. Claim: Process for the preparation of dyes of the general formula wherein X is a halogen atom, wherein d a d urch in that 1-amino-anthraquinone-3,4 (N) -benzacridon 3-oxy-4-halobenzoic or condenses the functional derivatives of these acids. References considered: U.S. Patent No. 2,568,966, Example 3.
DEC24778A 1961-08-02 1961-08-02 Process for the production of dyes Pending DE1176775B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEC24778A DE1176775B (en) 1961-08-02 1961-08-02 Process for the production of dyes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEC24778A DE1176775B (en) 1961-08-02 1961-08-02 Process for the production of dyes

Publications (1)

Publication Number Publication Date
DE1176775B true DE1176775B (en) 1964-08-27

Family

ID=7017722

Family Applications (1)

Application Number Title Priority Date Filing Date
DEC24778A Pending DE1176775B (en) 1961-08-02 1961-08-02 Process for the production of dyes

Country Status (1)

Country Link
DE (1) DE1176775B (en)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2568966A (en) * 1943-12-28 1951-09-25 Ciba Ltd 4-p-chlorobenzoylaminoanthraquinonebenzacridone

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2568966A (en) * 1943-12-28 1951-09-25 Ciba Ltd 4-p-chlorobenzoylaminoanthraquinonebenzacridone

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