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DE585897C - Process for the preparation of o-oxyazo dyes - Google Patents

Process for the preparation of o-oxyazo dyes

Info

Publication number
DE585897C
DE585897C DEI45044D DEI0045044D DE585897C DE 585897 C DE585897 C DE 585897C DE I45044 D DEI45044 D DE I45044D DE I0045044 D DEI0045044 D DE I0045044D DE 585897 C DE585897 C DE 585897C
Authority
DE
Germany
Prior art keywords
parts
benzo
dyes
preparation
dioxyquinoline
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
DEI45044D
Other languages
German (de)
Inventor
Dr Walther Benade
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 DEI45044D priority Critical patent/DE585897C/en
Application granted granted Critical
Publication of DE585897C publication Critical patent/DE585897C/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
    • C09B45/00—Complex metal compounds of azo dyes
    • C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
    • C09B45/14—Monoazo compounds
    • C09B45/16—Monoazo compounds containing chromium
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/02—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)

Description

DEUTSCHES REICHGERMAN EMPIRE

AUSGEGEBEN AM 12. OKTOBER 1933ISSUED ON OCTOBER 12, 1933

REICHSPATENTAMTREICH PATENT OFFICE

PAJENTSCHRIPAJENTSCHRI

Zusatz zum Patent 582Addition to patent 582

Gegenstand des Hauptpatents 582 688 ist ein Verfahren zur Herstellung für das Einbadchromverfahren geeigneter o-Oxyazofarbstoffe, das darin besteht, daß man solche diazotierten 2-Amino-i-oxybenzole, die eine Sulfonsäuregruppe enthalten, mit 2, 4-Dioxyö-naphthochinolin kuppelt.The subject of the main patent 582 688 is a process for the production for the single bath chrome process suitable o-oxyazo dyes, which consists in having such diazotized 2-amino-i-oxybenzenes, the one Containing sulfonic acid group, with 2, 4-Dioxyö-naphthochinolin clutch.

Wie weiterhin gefunden wurde, hat nicht nur das "2,4-Dioxy-a-naphthochinolin, welches als 7, 8-Benzo-2, 4-dioxychinolin zu bezeichnen ist, die- Eigenschaft, beim Kuppeln mit diazotierten 2-Amino-i-oxybenzolen, die eine Sulfonsäuregruppe enthalten, für das Einbadchromverfahren brauchbare Farbstoffe zu ergeben, sondern es sind dafür auch die beiden Isomeren, d.as 5, 6-Benzo-2, 4-dioxyehinolin und das 6, 7-Benzo-2, 4-dioxychinolin, geeignet.As was further found, not only has "2,4-Dioxy-a-naphthoquinoline, which as 7, 8-Benzo-2, 4-dioxyquinoline is to be designated, the property when coupling with diazotized 2-amino-i-oxybenzenes containing a sulfonic acid group for the One bath chromium process to give usable dyes, but there are also the two isomers, i.e. the 5, 6-benzo-2, 4-dioxyehinoline and the 6, 7-benzo-2, 4-dioxyquinoline, suitable.

Das 5, o-Benzo-2, 4-dioxychinolin kann auf einem ähnlichen Wege, wie er für die Herstellung des 2, 4-Dioxy-ct-naphthochinolins in den Berichten der Deutschen Chemischen Gesellschaft, Band 60, Seite 841, angegeben ist, durch Erhitzen von 2-Aminonaphthalin und Malonester erhalten, werden. 6, 7-Benzo-2, 4-dioxychinolin kann nach dem aus der Pa-The 5, o-Benzo-2, 4-dioxyquinoline can be used in a similar way as it is used for the production des 2,4-Dioxy-ct-naphthoquinoline in the reports of the German Chemical Society, Volume 60, page 841, by heating 2-aminonaphthalene and Obtained malonic esters. 6, 7-Benzo-2, 4-dioxyquinoline can after the from the Pa-

tentschrift 117167 bekannten Verfahren unter Verwendung von 2-Acetylaminonaphthalin-3-carbonsäure hergestellt werden.tentschrift 117167 known method under Use of 2-acetylaminonaphthalene-3-carboxylic acid getting produced.

Die durch Kuppeln mit diazotierten 2-Amino-1 -oxybenzolmonosulfonsäuren erhaltenen Farbstoffe zeigen die gleichen guten Eigenschaften wie die nach dem Hauptpatent erhältlichen Farbstoffe.The obtained by coupling with diazotized 2-amino-1 -oxybenzene monosulfonic acids Dyes show the same good properties as the dyes obtainable according to the main patent.

Beispiel 1example 1

22,4 Teile 4-Chlor-2-amino-l-oxybenzol-6-sulfonsäure werden mit etwa 300 Teilen Wasser angeschlämmt und nach Zusatz von 5 Teilen Salzsäure von 12° Be mit 6,9 Teilen Natriumnitrit bei 100C diazotiert. Die fertige Diazoverbinduqg läuft in eine kalte Lösung von 23 Teilen 5, o-Benzo-2, 4-dioxychinolin und 6 Teilen Natriumhydroxyd in etwa 500 Teilen Wasser. Nach beendeter Kupplung wird der Farbstoff in bekannter Weise aufgearbeitet. Er stellt in trockenem Zustande ein dunkles Pulver dar und färbt Wolle nach dem Einbadchromverfahren in violetten Tönen von sehr guter Wasch- ,und Walkechtheit.22.4 parts of 4-chloro-2-amino-l-oxybenzene-6-sulfonic acid are suspended in about 300 parts of water and diazotized by the addition of 5 parts of hydrochloric acid 12 ° Be with 6.9 parts of sodium nitrite at 10 0 C. The finished Diazoverbinduqg runs into a cold solution of 23 parts of 5, o-benzo-2,4-dioxyquinoline and 6 parts of sodium hydroxide in about 500 parts of water. After the coupling has ended, the dye is worked up in a known manner. When dry, it is a dark powder and dyes wool using the single-bath chrome process in violet shades of very good wash and milled fastness.

*) Von dem Patentsucher ist als der Erfinder angegeben worden:*) The patent seeker stated as the inventor:

Dr. Walther Benade in Dessau.Dr. Walther Benade in Dessau.

Beispiel 2Example 2

Eine aus 23,4. Teilen 4-Nitro-2-aminoi-oxybenzol-6-sulfonsäure, 6,9 Teilen Natriumnitrit und 5 Teilen Salzsäure von 120Be in etwa 500 Teilen Wasser bereitete Diazoverbindung wird zu einer mit Eis versetzten Auflösung von 23 Teilen 6, 7-Benzo-2, 4-dioxyehinolin und 20 Teilen Soda in 500 Teilen Wasser gegeben. Der entstandene Farbstori wird ausgesalzen und bildet getrocknet ein dunkles Pulver, das gut löslich ist und Wolle nach dem Einbadchr'omverfahren in granatfarbenen Tönen von guter Wasch- und Walkechtheit färbt.One out of 23.4. Parts of 4-nitro-2-amino-oxybenzene-6-sulfonic acid, 6.9 parts of sodium nitrite and 5 parts of hydrochloric acid of 12 0 Be in about 500 parts of water are prepared diazo compound to a solution of 23 parts of 6, 7-benzo with ice -2, 4-dioxyehinoline and 20 parts of soda in 500 parts of water. The resulting dye is salted out and, when dried, forms a dark powder that is easily soluble and colors wool in garnet-colored shades of good wash and milled fastness using the single-bath chrome process.

Claims (1)

Patentanspruch:Claim: Abänderung des Verfahrens zur Herstellung von o-Oxyazofarbstoffen nach Patent 582688, dadurch gekennzeichnet, daß man diazotierte 2-Amino-i-oxybenzolmonosulfonsäuren hier mit 5, 6- oder 6, 7-Benzo-2, 4-dioxychinolin kuppelt.Modification of the process for the production of o-oxyazo dyes according to Patent 582688, characterized in that diazotized 2-amino-i-oxybenzene monosulfonic acids here coupled with 5, 6- or 6, 7-benzo-2, 4-dioxyquinoline.
DEI45044D 1932-08-07 1932-08-07 Process for the preparation of o-oxyazo dyes Expired DE585897C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEI45044D DE585897C (en) 1932-08-07 1932-08-07 Process for the preparation of o-oxyazo dyes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEI45044D DE585897C (en) 1932-08-07 1932-08-07 Process for the preparation of o-oxyazo dyes

Publications (1)

Publication Number Publication Date
DE585897C true DE585897C (en) 1933-10-12

Family

ID=7191433

Family Applications (1)

Application Number Title Priority Date Filing Date
DEI45044D Expired DE585897C (en) 1932-08-07 1932-08-07 Process for the preparation of o-oxyazo dyes

Country Status (1)

Country Link
DE (1) DE585897C (en)

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