DE750233C - Process for the preparation of an anthraquinone dye - Google Patents

Process for the preparation of an anthraquinone dye

Info

Publication number
DE750233C
DE750233C DEI56137D DEI0056137D DE750233C DE 750233 C DE750233 C DE 750233C DE I56137 D DEI56137 D DE I56137D DE I0056137 D DEI0056137 D DE I0056137D DE 750233 C DE750233 C DE 750233C
Authority
DE
Germany
Prior art keywords
amino
preparation
anthraquinone dye
parts
dye
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
DEI56137D
Other languages
German (de)
Inventor
George Crowe Semple
Cecil Shaw
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Application granted granted Critical
Publication of DE750233C publication Critical patent/DE750233C/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
    • C09B43/00—Preparation of azo dyes from other azo compounds
    • C09B43/11—Preparation of azo dyes from other azo compounds by introducing hydrocarbon radicals or substituted hydrocarbon radicals on primary or secondary amino groups

Landscapes

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

Description

Verfahren zur Herstellung eines Anthrachinonfarbstoffes Aus der französischen Patentschrift 799 8IS ist die Herstellung eines Farbstoffes der Anthrachinonreihe durch Umsetzen vors t Amino-4-bromanthraclhinon-2-sulfonsäure mit 4-Amino-4'-oxy-I, I'-azobenzol-3'-carbonsäure bekannt.Process for the preparation of an anthraquinone dye From the French Patent 799 8IS is the preparation of a dye of the anthraquinone series by reacting before t amino-4-bromoanthraclhinone-2-sulfonic acid with 4-amino-4'-oxy-I, I'-azobenzene-3'-carboxylic acid known.

Es wurde nun gefunden, daß man durch Umsetzen von I-Amino-4-bromantlhraclhinon-2-sulfonsiiure und 4-Amino-I, I'-azobenzol in Gegenwart von Alkali und einem aus einer lKupferverbindung bestehenden Katalysator einen wasserlöslichen Anthrachinonfarbstotf herstellen kann, der Acetatkunstseide aus kochsalzhaltiger wässeriger Lösung in klaren, grünen Tönen von sehr guter 'Licht- und Waschechtheit färbt. Der bekannte Farbstoff zieht unter gleichen Bedingungen nicht auf Acetatlkunstseide. Beispiel Ein Gemisch aus einer Lösung von Ioo Teilen t - amrino - 4l - bromanthrachinon-2-sulfonsaurem Natrium in I65o Teilen Wasser, 5o Teilen 4-Amino-I, I'-azobenzol, 25 Teilen Natriumcarbonat, I oo Teilen Natriumbicarbonat, Io Teilen Cuprochlorid und 275 Teilen Äthylalkohol wird am Rückflußkühler 48 Stunden lang gekocht. Dabei geht die Farbe der Lösung von Orangerot über Gelblichbraun in Olivgrün über, urnd es scheidet sich schließlich ein grüner Niederschlag ab. Dieser Niederschlag wird ahfiltriert. Etwa nicht umgesetztes I-anino-@-bromanthrachinon-2-sulfonsaures Natrium wird mit Wasser ausgewaschen, und etwa nicht umgesetztes 4-Amino-t, I'-azobenzol wird mnit Wasser ausgewaschen, und etwa nicht umgesetztes 4-2\illirio-i, i'-azolienzol wird mit Benzol ausgezogen. Der so gereinigte dunkelgrüne Farbstoff - I Amino-4-4'-phenylazophenyläminöänthrachinon-2-sulfonsäure - löst sich in konzentrierter Schwefelsäure mit grüner Farbe.It has now been found that by reacting I-amino-4-bromantlhraclhinone-2-sulfonic acid and 4-amino-I, I'-azobenzene in the presence of alkali and one of a copper compound existing catalyst can produce a water-soluble anthraquinone dye, the acetate silk from saline aqueous solution in clear, green tones dyes of very good light and wash fastness. The well-known dye takes under same conditions not on acetate silk. Example A mixture of a Solution of 100 parts of t - amrino - 4l - bromoanthraquinone-2-sulfonic acid sodium in 1650 parts of water, 50 parts of 4-amino-I, I'-azobenzene, 25 parts of sodium carbonate, 100 parts sodium bicarbonate, 10 parts cuprous chloride and 275 parts ethyl alcohol is refluxed for 48 hours. This is where the color of the solution goes from orange-red to yellowish-brown to olive-green, and finally it separates a green precipitate. This precipitate is filtered off. Something that has not been implemented I-anino - @ - bromoanthraquinone-2-sulfonic acid sodium is washed out with water, and any unreacted 4-amino-t, I'-azobenzene is washed out with water, and any unreacted 4-2 \ illirio-i, i'-azolienzol becomes with benzene moved out. The dark green dye purified in this way - I Amino-4-4'-phenylazophenyläminöanthraquinone-2-sulfonic acid - dissolves in concentrated sulfuric acid with a green color.

Das Natriumsalz des Farbstoffes ist in Wasser mit grüner Farbe löslich und färbt Acetatkunstseide aus wässeriger, kochsalzhaltiger Lösung in grünen Tönen von sehr guter Licht- und Waschechtheit.The sodium salt of the dye is soluble in water with a green color and dyes acetate rayon from aqueous, saline solution in green tones very good lightfastness and washfastness.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Anthrachinonfarbstoffes, dadurch gekennzeichnet, daß I-Amino-4-bromanthrachitnon-a-sulfonsäure mit 4- Amino-I, I'-azobenzol in Gegenwart von Alkali und einem aus einer Kupferverbindung bestehenden Katalysator umgesetzt wird.PATENT CLAIM: Process for the production of an anthraquinone dye, characterized in that I-amino-4-bromoanthrachitnon-a-sulfonic acid with 4- amino-I, I'-azobenzene in the presence of an alkali and a copper compound Catalyst is implemented.
DEI56137D 1936-07-22 1936-10-13 Process for the preparation of an anthraquinone dye Expired DE750233C (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB750233X 1936-07-22

Publications (1)

Publication Number Publication Date
DE750233C true DE750233C (en) 1944-12-27

Family

ID=10496259

Family Applications (1)

Application Number Title Priority Date Filing Date
DEI56137D Expired DE750233C (en) 1936-07-22 1936-10-13 Process for the preparation of an anthraquinone dye

Country Status (1)

Country Link
DE (1) DE750233C (en)

Similar Documents

Publication Publication Date Title
DE750233C (en) Process for the preparation of an anthraquinone dye
DE632083C (en) Process for the production of acidic dyes of the anthraquinone series
DE557196C (en) Process for the production of chromium-containing azo dyes
DE657628C (en) Manufacture of dyes
DE638338C (en) Process for the preparation of dyes of the safranine series
DE673182C (en) Process for the preparation of o-oxyazo dyes
DE734044C (en) Process for the preparation of acidic anthraquinone dyes
DE578415C (en) Process for the representation of gray, blue-gray to gray-gray dyes of the anthraquinone series
DE221433C (en)
DE666408C (en) Process for the production of chromating dyes of the anthraquinone series
DE749166C (en) Process for the preparation of monoazo dyes
DE247648C (en)
DE615093C (en) Process for the preparation of an azo dye
DE571397C (en) Process for the preparation of disazo dyes
DE418940C (en) Process for dyeing artificial silk from acidyl celluloses, cellulose ethers or their conversion products
DE501232C (en) Process for the preparation of dyes of the anthraquinone series
DE940243C (en) Process for the production of Kuepen dyes of the anthraquinone series
CH200999A (en) Process for the preparation of an azo dye.
CH214406A (en) Process for the preparation of a dye of the anthraquinone series.
CH209521A (en) Process for the preparation of a copper complex containing stilbene azo dye.
CH183453A (en) Process for the preparation of an azo dye.
CH200926A (en) Process for the preparation of a chromable anthraquinone dye.
CH200925A (en) Process for the preparation of a chromable anthraquinone dye.
CH252136A (en) Process for the preparation of a new monoazo dye.
CH222800A (en) Process for the preparation of a leuco sulfuric acid ester of a vat dye.