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DE645185C - Process for the production of direct dyes of the anthraquinone series - Google Patents

Process for the production of direct dyes of the anthraquinone series

Info

Publication number
DE645185C
DE645185C DEG91246D DEG0091246D DE645185C DE 645185 C DE645185 C DE 645185C DE G91246 D DEG91246 D DE G91246D DE G0091246 D DEG0091246 D DE G0091246D DE 645185 C DE645185 C DE 645185C
Authority
DE
Germany
Prior art keywords
direct dyes
production
anthraquinone series
series
cinnamic acid
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
DEG91246D
Other languages
German (de)
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.)
Chemische Ind Ges
GESELLSCHAFT fur CHEMISCHE INDUSTRIE
BASF Schweiz AG
Original Assignee
Chemische Ind Ges
GESELLSCHAFT fur CHEMISCHE INDUSTRIE
Gesellschaft fuer Chemische Industrie in Basel CIBA
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 Chemische Ind Ges, GESELLSCHAFT fur CHEMISCHE INDUSTRIE, Gesellschaft fuer Chemische Industrie in Basel CIBA filed Critical Chemische Ind Ges
Application granted granted Critical
Publication of DE645185C publication Critical patent/DE645185C/en
Expired 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
    • 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
    • C09B1/34—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups sulfonated
    • C09B1/343—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups sulfonated only sulfonated in the anthracene nucleus

Landscapes

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

Description

Verfahren zur Herstellung von direkt ziehenden Farbstoffen der Anthrachinonreihe Es wurde gefunden, daß man neue, direkt ziehende Farbstoffe der Anthrachinonreihe in welcher R einen Rest der Diphenylreihe bedeutet, die am Diphenylrest befindliche Aminogruppe mit geeigneten Zimtsäurederivaten, wie Zimtsäurechlorid, acidyliert.Process for the preparation of direct dyes of the anthraquinone series It has been found that new direct dyes of the anthraquinone series can be produced in which R denotes a residue of the diphenyl series, the amino group on the diphenyl residue is acidylated with suitable cinnamic acid derivatives, such as cinnamic acid chloride.

Die neuen Farbstoffe sind durch eine ausgezeichnete Affinität zur pflanzlichen Faser sowie für Textilien aus regenerierter Cellulose ausgezeichnet und färben diese Materialien in blaugrünen Tönen, die sich durch ihre Gleichmäßigkeit, ihre Reinheit und ihre vortreffliche Lichtechtheit auszeichnen. In dieser Beziehung übertreffen sie merklich den erhält, wenn man in Produkten der allgemeinen Formel bekannten Farbstoff, der hergestellt wird durch Einwirkung von Zimtsäurechlorid auf das Kondensationsprodukt aus i Mol I-Amino-4-bromanthrachinon-2-sulfonsäure und I Mol p-Phenyldiamin. Die neuen Farbstoffe können ferner zum Färben von Lacken, Firnissen, Massen usw. verwendet werden. Beispiel 1.E,5 Teile des Kondensationsproduktes aus t -Amino-d.-brom-anthrachinon-2-sulfonsäure und Benzidin werden in 5oo Teilen Wasser und 5oo Teilen Paridin gelöst. Unter gutem Rühren tropft man I8 Teile geschmolzene, Zimtsäurechlorid zu und erwärmt allmäh- ]ich bis auf 85°. Nach dem Erkalten tüä Aus salzen filtriert man den ausgeschieden Farbstoff ab. Er färbt auf Baumwolle ein, reines grünstichiges Blau voll vorzüglicher Lichtechtheit.The new dyes have an excellent affinity for vegetable fibers as well as for textiles made of regenerated cellulose and dye these materials in blue-green tones, which are characterized by their uniformity, their purity and their excellent lightfastness. In this respect they significantly exceed the dyestuff known in products of the general formula which is prepared by the action of cinnamic acid chloride on the condensation product of 1 mole of 1-amino-4-bromoanthraquinone-2-sulfonic acid and 1 mole of p-phenylenediamine. The new dyes can also be used for coloring paints, varnishes, compositions, etc. Example 1.E, 5 parts of the condensation product of t -amino-d.-bromo-anthraquinone-2-sulfonic acid and benzidine are dissolved in 500 parts of water and 500 parts of paridine. 18 parts of molten cinnamic acid chloride are added dropwise with thorough stirring and the mixture is gradually heated. ] I up to 85 °. After cooling down, tüä The excreted salts are filtered off Dye off. He dyes on cotton, pure greenish blue full of excellent lightfastness.

Analoge Resultate erhält man, wenn man stattdesKondensationsproduktesaus I-Amino-4-bromanthrachinon-2-sulfonsäiure und Benzidin ein solches verwendet, in welchem das Benzidin durch o-Tolidin, o-Dianisidin ersetzt worden ist.Analogous results are obtained if instead of the condensation product I-Amino-4-bromoanthraquinone-2-sulfonic acid and benzidine used one such in which the benzidine has been replaced by o-tolidine, o-dianisidine.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung voll direkt ziehenden Farbstoffen der Anthrachinonreihe, dadurch gekennzeichnet, daß man in Produkten der allgemeinen Formel in welcher R einen Rest der Diphenylreihe bedeutet, die am Diphenylrest befindliche Aminogruppe mit geeigneten Zimtsäurederivaten, wie Zimtsäurechlorid, acidvliert.PATENT CLAIM: Process for the production of fully direct dyes of the anthraquinone series, characterized in that products of the general formula in which R is a residue of the diphenyl series, the amino group on the diphenyl residue is acidified with suitable cinnamic acid derivatives, such as cinnamic acid chloride.
DEG91246D 1934-11-08 1935-09-27 Process for the production of direct dyes of the anthraquinone series Expired DE645185C (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH645185X 1934-11-08

Publications (1)

Publication Number Publication Date
DE645185C true DE645185C (en) 1937-05-22

Family

ID=4525717

Family Applications (1)

Application Number Title Priority Date Filing Date
DEG91246D Expired DE645185C (en) 1934-11-08 1935-09-27 Process for the production of direct dyes of the anthraquinone series

Country Status (1)

Country Link
DE (1) DE645185C (en)

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