DE588897C - Process for the production of water-insoluble azo dyes - Google Patents

Process for the production of water-insoluble azo dyes

Info

Publication number
DE588897C
DE588897C DEI43786D DEI0043786D DE588897C DE 588897 C DE588897 C DE 588897C DE I43786 D DEI43786 D DE I43786D DE I0043786 D DEI0043786 D DE I0043786D DE 588897 C DE588897 C DE 588897C
Authority
DE
Germany
Prior art keywords
benzocarbazole
dihydro
oxy
water
carboylamino
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
DEI43786D
Other languages
German (de)
Inventor
Dr Otto Goll
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 DEI43786D priority Critical patent/DE588897C/en
Priority to FR751083D priority patent/FR751083A/en
Application granted granted Critical
Publication of DE588897C publication Critical patent/DE588897C/en
Expired legal-status Critical Current

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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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
    • C09B29/18—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides
    • C09B29/22—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides of heterocyclic compounds
    • 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

Landscapes

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

Description

Es wurde gefunden, daß1 man zu wertvollen wasserunlöslichen Azofarbstoffen dadurch gelangt, daß man die Arylide der 2-Oxy-5, 6-dihydro-7, S-benzocarbazol-3-carbonsäure in Substanz oder auf der Faser mit Diazoverbindungen kuppelt und dabei die Komponenten derart wählt, daß sie keine wasserlöslich machende Gruppe, wie die Sulfonsäure- oder die Carboxylgruppe, enthalten.It has been found that 1 leads thereby valuable water-insoluble azo dyes, that couples the Arylide of 2-oxy-5, 6-dihydro-7, S-benzocarbazole-3-carboxylic acid in bulk or on the fiber with diazo compounds, while the Components are chosen so that they do not contain a water-solubilizing group such as the sulfonic acid or the carboxyl group.

Je nach Wahl der Komponenten erhält man verschiedene Farbtöne, die, auf der Faser hergestellt, bemerkenswerte Echtheitseigenschaften besitzen.Depending on the choice of components, you get different shades of color, the, on the fiber manufactured, possess remarkable fastness properties.

Die bei dem Verfahren verwendeten Arylide der 2-Oxy~5, 6-dihydro-7, S-benzocarbazol-3-carbonsäure sind z. B. erhältlich -nach dem Verfahren des Patents 588 042.The arylides of 2-oxy ~ 5, 6-dihydro-7, S-benzocarbazole-3-carboxylic acid used in the process are z. B. obtainable by the method of patent 588 042.

Beispielexample

Gut ausgekochtes und getrocknetes Baumwollgarn wird mit einer Lösung, die 2,5 g i-(2'-Oxy-5', 6'-dihydro-7', 8'-benzocarbazol-3'-carboylamino)-4-methoxybenzol, 10 ecm Natronlauge von 340 Be, 10 ecm Türkischrotöl (5Oprozentig) im Liter enthält, getränkt, gründlich abgewunden und, ohne zu trocknen, in einer mit Acetat abgestumpften Diazolösung, die 2 g 2, 5-Dichlor-i-ammobenzol im Liter enthält, entwickelt, gespült und geseift. Man erhält auf diese Weise ein schönes und echtes Orangebraun.Well-boiled and dried cotton yarn is mixed with a solution containing 2.5 g of i- (2'-oxy-5 ', 6'-dihydro-7', 8'-benzocarbazole-3'-carboylamino) -4-methoxybenzene, 10 ecm sodium hydroxide solution of 34 0 Be, 10 ecm Turkish red oil (50 percent) per liter, soaked, thoroughly wound and, without drying, in a diazo solution truncated with acetate, which contains 2 g of 2,5-dichloro-i-ammobenzene per liter, developed, rinsed and soaped. In this way you get a nice and real orange brown.

Nachstehend werden weitere Farbstoffe und ihre Farbtöne angegeben, die nach der vorangehend beschriebenen Arbeitsweise hergestellt werden können:Further dyes and their hues are given below, which are selected according to the the working method described above can be produced:

KupplungskomponenteCoupling component

DiazokomponenteDiazo component

Farbtonhue

i-(2'-Oxy-5', 6'-dihydro-7', 8'-benzocarbazol-3'-carboylamino)-4-methoxybenzol i- (2'-Oxy-5 ', 6'-dihydro-7', 8'-benzocarbazole-3'-carboylamino) -4-methoxybenzene

i-(2'-Oxy-5', 6'-dihydro-7', 8'-benzocarbazol-3'-carboylamino)-4-methoxybenzol i- (2'-Oxy-5 ', 6'-dihydro-7', 8'-benzocarbazole-3'-carboylamino) -4-methoxybenzene

i-(2'-Oxy-5', 6'-dihydro-7', 8'-benzocarbazol-3'-carboylamino)-4-methoxybenzol i- (2'-Oxy-5 ', 6'-dihydro-7', 8'-benzocarbazole-3'-carboylamino) -4-methoxybenzene

i-(2'-Oxy-5', 6'-dihydro-7', 8'-benzocarbazol-3'-carboylamino) -4-methoxybenzoli- (2'-Oxy-5 ', 6'-dihydro-7', 8'-benzocarbazole-3'-carboylamino) -4-methoxybenzene

4-Chlor- 2-amino- i-methylbenzol
6-Chlor - 2-amino- t-methylbenzol4-chloro-2-amino-i-methylbenzene
6-chloro-2-amino-t-methylbenzene

4-Chlor- 2-amino - i-methoxybenzol 4-chloro-2-amino-i-methoxybenzene

3, 2'-Dimethyl-4-aminoazobenzol3, 2'-dimethyl-4-aminoazobenzene

rotstichiggelbbraun reddish yellow brown

gelbbraunyellow-brown

braunBrown

rotbraunred-brown

*) Von dem Patentsucher sind als die Erfinder angegeben worden:*) The patent seeker indicated the following as the inventors:

Dr. Wilhelm Neelmeier in Leverkusen, Dr. Heinrich Morschel und Dr. Otto GoIl in Leverkusen,Dr. Wilhelm Neelmeier in Leverkusen, Dr. Heinrich Morschel and Dr. Otto GoIl in Leverkusen,

Köln-DeutsCologne-German

Kupplungskomponente DiazokomponenteCoupling component diazo component

Farbtonhue

i-(2'-Oxy-5', 6'-dihydro-7', 8'-benzocarbazol-3'-carboylamino)-2-rnethylbenzol i- (2'-Oxy-5 ', 6'-dihydro-7', 8'-benzocarbazole-3'-carboylamino) -2-methylbenzene

i-(2'-Oxy-5', 6'-dihydro-7', 8'-benzocarbazol-3'-carboylamino) -2-methylbenzoli- (2'-Oxy-5 ', 6'-dihydro-7', 8'-benzocarbazole-3'-carboylamino) -2-methylbenzene

i:.(2'-Oxy-5', 6'-dihydro-7', ö'-benzocarbazol-3'-carboylamino)-4-chlorbenzol i :. (2'-Oxy-5 ', 6'-dihydro-7', δ'-benzocarbazole-3'-carboylamino) -4-chlorobenzene

• i-(2'-0xy-5', 6'-dihydro-7', 8'-benzocarbazol-. 3'-carboylamino)-4-chlorbenzol• i- (2'-oxy-5 ', 6'-dihydro-7', 8'-benzocarbazole-. 3'-carboylamino) -4-chlorobenzene

i-(2'-0xy-5', 6'-dihydro-7', 8'-benzocarbazol-3'-carboylamino) -3-ehlorbenzoli- (2'-0xy-5 ', 6'-dihydro-7', 8'-benzocarbazole-3'-carboylamino) -3-chlorobenzene

i-(2'-Oxy-5', 6'-dihydro-7', 8'-benzocarbazol-3'-carboylamino) -3-chlorbenzoli- (2'-Oxy-5 ', 6'-dihydro-7', 8'-benzocarbazole-3'-carboylamino) -3-chlorobenzene

i-(2'-Oxy-5', 6'-dihydro-7', 8'-benzocarbazol-3'-carbbylamino)-2-methyl-4-methoxybenzol i- (2'-Oxy-5 ', 6'-dihydro-7', 8'-benzocarbazole-3'-carbbylamino) -2-methyl-4-methoxybenzene

i-(2'-0xy-5', 6'-dihydro-7', 8'-benzocarbazol-3'-carboylamino)-2-methyl-4-methoxyben- zoli- (2'-0xy-5 ', 6'-dihydro-7', 8'-benzocarbazole-3'-carboylamino) -2-methyl-4-methoxyben- zol

2,4'-Dimethyl- 2'- nitro - 3 - methoxy-4-aminoazobenzol 2,4'-dimethyl-2'-nitro-3-methoxy-4-aminoazobenzene

4-Nitro- 2 -amino- i-methylbenzol 6-Chlor-2-amino-1 -methylbenzol4-nitro-2-amino-i-methylbenzene 6-chloro-2-amino-1-methylbenzene

6-Amino-4-benzoylamino-i, 3-dimethylbenzol 6-amino-4-benzoylamino-1,3-dimethylbenzene

3-Chlor-i-aminobenzol 4-Chlor-2-amino-1-methylbenzol 4-Nitro- 2-amino- i-methylbenzol3-chloro-i-aminobenzene 4-chloro-2-amino-1-methylbenzene 4-nitro-2-amino-i-methylbenzene

6-Chlor-2-amino-1 -methylbenzol6-chloro-2-amino-1-methylbenzene

35 tiefrotbraun 35 deep red brown

gelbbraunyellow-brown

rotstichiggelbbraun reddish yellow brown

orangebraun gelbbraunorange-brown yellow-brown

gelbbraunyellow-brown

rotstichiggelbbraun reddish yellow brown

gelbbraunyellow-brown

Claims (1)

Patentanspruch: Verfahren zur Herstellung von wasserunlöslichen AzofarbstofEen in Substanz oder auf der Faser, dadurch gekennzeichnet, daß man die Arylide der 2-Oxy-5, 6-dihydro-7, 8-benzocarbazol-3-carbonsäure in Substanz oder auf der Faser mit Diazoverbindungen kuppelt und dabei die Komponenten derart -wählt, daß sie keine wasserlöslich machende Gruppe enthalten.Claim: Process for the production of water-insoluble Azo dyes in substance or on the fiber, characterized that the arylides of 2-oxy-5, 6-dihydro-7, 8-benzocarbazole-3-carboxylic acid Couples in substance or on the fiber with diazo compounds and thereby -selects the components in such a way that they do not contain any contain water-solubilizing group.
DEI43786D 1932-02-19 1932-02-19 Process for the production of water-insoluble azo dyes Expired DE588897C (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
DEI43786D DE588897C (en) 1932-02-19 1932-02-19 Process for the production of water-insoluble azo dyes
FR751083D FR751083A (en) 1932-02-19 1933-02-18 New water insoluble azo dyes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEI43786D DE588897C (en) 1932-02-19 1932-02-19 Process for the production of water-insoluble azo dyes

Publications (1)

Publication Number Publication Date
DE588897C true DE588897C (en) 1933-11-29

Family

ID=7191112

Family Applications (1)

Application Number Title Priority Date Filing Date
DEI43786D Expired DE588897C (en) 1932-02-19 1932-02-19 Process for the production of water-insoluble azo dyes

Country Status (2)

Country Link
DE (1) DE588897C (en)
FR (1) FR751083A (en)

Also Published As

Publication number Publication date
FR751083A (en) 1933-08-26

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