DE589348C - Process for the production of azo dyes - Google Patents

Process for the production of azo dyes

Info

Publication number
DE589348C
DE589348C DEI43785D DEI0043785D DE589348C DE 589348 C DE589348 C DE 589348C DE I43785 D DEI43785 D DE I43785D DE I0043785 D DEI0043785 D DE I0043785D DE 589348 C DE589348 C DE 589348C
Authority
DE
Germany
Prior art keywords
brown
chloro
aminobenzene
oxycarbazole
benzo
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
DEI43785D
Other languages
German (de)
Inventor
Dr Heinrich Morschel
Dr Wilhelm Neelmeier
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 DEI43785D priority Critical patent/DE589348C/en
Application granted granted Critical
Publication of DE589348C publication Critical patent/DE589348C/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00Monoazo dyes prepared by diazotising and coupling
    • C09B29/10Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
    • C09B29/18Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides
    • C09B29/22Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides of heterocyclic compounds

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

Description

Es wurde gefunden, daß man zu wertvollen, wasserunlöslichen Azofarbstoffen dadurch gelangt, daß man die Arylide von Benzo-a-oxycarbazol-ß-carbonsäuren mit Diazoverbindungen in Substanz oder -auf der Faser kuppelt und dabei die Komponenten derart wählt, daß sie keine wasserlöslich machende Gruppe, wie die Sulfonsäure- oder Carboxylgruppe, enthalten.It has been found that valuable, water-insoluble azo dyes can thereby be obtained arrives that the arylides of benzo-a-oxycarbazole-ß-carboxylic acids with diazo compounds in substance or -on the fiber couples and thereby the components Chooses such that they do not have a water-solubilizing group, such as the sulfonic acid or Carboxyl group.

in* Je nach Wahl "der Komponenten erhält man Farbstoffe von verschiedenen Nuancen, die, auf der Faser hergestellt, bemerkenswerte Echtheiten besitzen.in * Depending on the choice "of the components dyes of various shades that, produced on the fiber, are remarkable Possess fastnesses.

Die bei dem Verfahren als Kupplungskom-The coupling components used in the process

i'g- ponenten verwendeten Arylide von Benzo-2-oxycarbazol"3-carbonsäuren sind z. B. erhältlich nach Patent 588 043.i'g components used arylides of benzo-2-oxycarbazole "3-carboxylic acids are z. B. available according to patent 588 043.

; Beispieli; Example i

• Gut ausgekochtes und getrocknetes Baumwollgarn wird mit einer Lösung von 3 g 1" (S'> 6' - Benzo - 2' - oxycarbazol - 3' - carboyl amino)-4-chlorbenzol, 10 ecm Natronlauge• Well-boiled and dried cotton yarn is mixed with a solution of 3 g of 1 "(S '>6' - Benzo - 2 '- oxycarbazole - 3' - carboyl amino) -4-chlorobenzene, 10 ecm of sodium hydroxide solution

von 340 Be und 10 ecm Türkischrotöl 5oprozentig im Liter imprägniert, gründlich abgewunden und, ohne zu trocknen, in einer mit Acetat abgestumpften Diazolösung, die 2 g i-Methyl-4-chlor-2-aminobenzol im Liter enthält, entwickelt, gespült und geseift. Man erhält so ein schönes und echtes gelbstichiges Braun. ■of 34 0 Be and 10 ecm Turkish red oil 5% impregnated in the liter, thoroughly wound and, without drying, developed, rinsed and, without drying, in a diazo solution truncated with acetate, which contains 2 g i-methyl-4-chloro-2-aminobenzene per liter soaped. You get a beautiful and real yellowish brown. ■

Beispiel 2 Example 2

Gut ausgekochtes und getrocknetes Baumwollgarn wird mit einer Lösung von 1,2 g ι-(7', 8'-Benzo-2'-oxycarbazol-3'-carboylamino)-4-methoxybenzol, 10 ecm Natronlauge von 34° Be und 10 ecm Türkischrotöl 5oprozentig im Liter imprägniert, gründlich abgewunden und, ohne zu trocknen, in einer mit Acetat abgestumpften Diazolösung, die 2 g 2-Chlor-i-aminobenzol im Liter enthält, entwickelt, gespült und geseift. Man erhält so ein schönes und sehr echtes Gelbbraun.Well-boiled and dried cotton yarn is mixed with a solution of 1.2 g ι- (7 ', 8'-benzo-2'-oxycarbazole-3'-carboylamino) -4-methoxybenzene, 10 ecm caustic soda solution of 34 ° Be and 10 ecm Turkish red oil Impregnated by 5% per liter, carefully wound and, without drying, in one diazo solution blunted with acetate, which contains 2 g of 2-chloro-i-aminobenzene per liter, developed, rinsed and soaped. You get a beautiful and very real yellow-brown.

Nachstehend wird eine Reihe weiterer nach dem vorliegenden Verfahren erhältlicher Farbstoffe nebst ihren Farbtönen angeführt.A number of others will now be made available by the present process Dyes and their shades are listed.

KupplungskomponenteCoupling component DiazokomponenteDiazo component Farbtonhue τ~{5'> 6'-Benzo-2'-oxycarbazol-3'-car-
boylamino) -4-chlorbenzol
τ ~ {5 '> 6'-Benzo-2'-oxycarbazole-3'-car-
boylamino) -4-chlorobenzene
3-Chlor-i-amüiobenzol
2-Chlor-i-aminobenzol
4-Nitro-i-methoxy-2-aminobenzol
3-chloro-i-amiobenzene
2-chloro-i-aminobenzene
4-nitro-i-methoxy-2-aminobenzene
khakibraun
gelbbraun
braun ,
khaki brown
yellow-brown
Brown ,

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

Dr. Wilhelm Neelmeier in Leverkusen und- Dr. Heinrich Morschel in Köln-Deuts.Dr. Wilhelm Neelmeier in Leverkusen and- Dr. Heinrich Morschel in Cologne-Deuts.

Kup plungs komponenteCoupling component DiazokomponenteDiazo component Farbtonhue ι - (5', 6' -Benzo-2' -oxycarbazol^'-car-ι - (5 ', 6' -Benzo-2 '-oxycarbazole ^' - car- 4-Chlor-i-methyl-2-aminobenzol4-chloro-i-methyl-2-aminobenzene gelbstichigyellowish 55 boylamino) -3-chlorbenzolboylamino) -3-chlorobenzene braunBrown 2-Chlor-i-aniinobenzol2-chloro-i-aniinobenzene gelbbraunyellow-brown 5-Chlor-i-methyl-2-aminobenzol5-chloro-i-methyl-2-aminobenzene braunBrown 5-Nitro-i-methoxy-2-aminobenzol5-nitro-i-methoxy-2-aminobenzene rotstichigreddish IOIO braunBrown ι - (5', 6' - Benzo - 2' - oxycarbazol-3' - car -ι - (5 ', 6' - Benzo - 2 '- oxycarbazole-3' - car - 3-Chlor-i-aminobenzol3-chloro-i-aminobenzene khakibraunkhaki brown boylamino)-2-methylbenzolboylamino) -2-methylbenzene 2-Chlor-i-aminobenzol2-chloro-i-aminobenzene braunBrown 4-Chlor-i-methyl-2-aminobenzol4-chloro-i-methyl-2-aminobenzene gelbbraunyellow-brown 1515th 5-Nitro-i-methoxy-2-aminobenzol5-nitro-i-methoxy-2-aminobenzene rotstichig-
braun
reddish
Brown
ι-(Y, 8'-Benzo-2'-oxycarbazol-2'-car-ι - (Y, 8'-Benzo-2'-oxycarbazole-2'-car- 4-Chlor-i-methyl-2-aminobenzol4-chloro-i-methyl-2-aminobenzene braunBrown boylamino) -4-methoxybenzolboylamino) -4-methoxybenzene 2-Chlor-4-benzoylamino-5-methoxy-2-chloro-4-benzoylamino-5-methoxy- rotstichigreddish 2020th i-amhiobenzoli-amhiobenzene braunBrown i-(7', 8'-Benzo-2'-oxycarbazol-3'-car-i- (7 ', 8'-Benzo-2'-oxycarbazole-3'-car- 2, 5-Dichlor-i-aminobenzol 2, 5-dichloro-i-aminobenzene orangebraunorange brown boj'lamino)-2-methyl-4-methoxybenzolboj'lamino) -2-methyl-4-methoxybenzene 2, 3'-Dimethyl-4-aminoazobenzol2,3'-dimethyl-4-aminoazobenzene rotstichig-
dunkelbraun
reddish
dark brown
2 - Chlor^-benzoylamino-S-methoxy-2 - chloro ^ -benzoylamino-S-methoxy- rotstichigreddish 2525th i-aminobenzoli-aminobenzene braunBrown i-(7', 8'-Benzo-2'-oxycarbazol-3'-car-i- (7 ', 8'-Benzo-2'-oxycarbazole-3'-car- 4-Chlor-2-arnino-i-methylbenzol4-chloro-2-amino-i-methylbenzene gelbbraunyellow-brown boylamino) -3-chlorbenzolboylamino) -3-chlorobenzene 5-Chlor-2-amino-i-methylbenzol5-chloro-2-amino-i-methylbenzene braunBrown 5-Nitro-2-amino-i-methoxybenzol5-nitro-2-amino-i-methoxybenzene rotbraunred-brown 3030th i-(Y, 8'-Benzo-2'-oxycarbazol-3'-car-i- (Y, 8'-Benzo-2'-oxycarbazole-3'-car- 4-Chlor-2-amino-i-methylbenzol4-chloro-2-amino-i-methylbenzene gelbbraunyellow-brown boylamino)-2-chlorbenzolboylamino) -2-chlorobenzene 2 - Chlor-4-benzoylarnino-5-methoxy-2 - chloro-4-benzoylarnino-5-methoxy- rotstichigreddish i-aminobenzoli-aminobenzene braunBrown 4-Nitro-2-amino-i-methylbenzol4-nitro-2-amino-i-methylbenzene orangebraunorange brown 3535 ι - (Y, 8' - Benzo - 2' - oxycarbazol - 3' - car -ι - (Y, 8 '- Benzo - 2' - oxycarbazole - 3 '- car - 4-Chlor-2-amino-i-methylbenzol4-chloro-2-amino-i-methylbenzene orangebraunorange brown boylamino)-4-chlorbenzolboylamino) -4-chlorobenzene 3, 2'-Dimethyl-4-aminoazobenzol3, 2'-dimethyl-4-aminoazobenzene rotstichigreddish braunBrown i-(7', 8'-Benzo-2'-oxycarbazol-3'-car-i- (7 ', 8'-Benzo-2'-oxycarbazole-3'-car- 3-Nitro-i-aminobenzol3-nitro-i-aminobenzene rotstichig-reddish 4040 boylamino)-2-methyl-4-chlorbenzolboylamino) -2-methyl-4-chlorobenzene gelbbraunyellow-brown 2, 5-Dichlor-i-aminobenzol2,5-dichloro-i-aminobenzene orangebraunorange brown z, 3'-Dimethyl-4-aminoazobenzol z, 3'-Dimethyl-4-aminoazobenzene rotbraunred-brown

Claims (1)

45 Patentanspruch:45 claim: Verfahren zur Herstellung von wasserunlöslichen Azofarbstoffen in Substanz oder auf der Faser, dadurch gekennzeichnet, daß man die Arylide von Benzo-Process for the preparation of water-insoluble azo dyes in substance or on the fiber, characterized in that the arylides of benzo- 2-oxycarbazol-3-carbonsäuren in Substanz oder auf der Faser mit Diazover- 95 bindungen kuppelt und dabei die Komponenten so wählt, daß sie keine wasserlöslich machenden Gruppe enthalten.2-oxycarbazole-3-carboxylic acids in substance or coupling it to the fiber with diazo compounds and choosing the components so that they are not water-soluble making group included.
DEI43785D 1932-02-19 1932-02-19 Process for the production of azo dyes Expired DE589348C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEI43785D DE589348C (en) 1932-02-19 1932-02-19 Process for the production of azo dyes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEI43785D DE589348C (en) 1932-02-19 1932-02-19 Process for the production of azo dyes

Publications (1)

Publication Number Publication Date
DE589348C true DE589348C (en) 1933-12-06

Family

ID=7191111

Family Applications (1)

Application Number Title Priority Date Filing Date
DEI43785D Expired DE589348C (en) 1932-02-19 1932-02-19 Process for the production of azo dyes

Country Status (1)

Country Link
DE (1) DE589348C (en)

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