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DE539116C - Process for the preparation of water-insoluble azo dyes - Google Patents

Process for the preparation of water-insoluble azo dyes

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Publication number
DE539116C
DE539116C DEI39034D DEI0039034D DE539116C DE 539116 C DE539116 C DE 539116C DE I39034 D DEI39034 D DE I39034D DE I0039034 D DEI0039034 D DE I0039034D DE 539116 C DE539116 C DE 539116C
Authority
DE
Germany
Prior art keywords
water
preparation
azo dyes
insoluble azo
black
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
DEI39034D
Other languages
German (de)
Inventor
Dr Fritz Ballauf
Dr Heinrich Hefner
Dr Albert Schmelzer
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 DEI39034D priority Critical patent/DE539116C/en
Application granted granted Critical
Publication of DE539116C publication Critical patent/DE539116C/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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Description

Verfahren zur Darstellung von wasserunlöslichen Azofarbstoffen Es wurde gefunden, daß man zu wertvollen wasserunlöslichen Azofarbstoffen gelangen kann, wenn man die Diazoverbindungen von aromatischen oder heterocyclischen unsulfonierten Aminen oder ihren Derivaten mit den Aryliden der o-0xynaphthocarbazolcarbonsäuren für sich oder auf der Faser kuppelt. Man erhält auf diese Weise Farbstoffe der verschiedensten Nuancen, die, auf der Faser hergestellt, ausgezeichnete Echtheitseigenschaften besitzen.Process for the preparation of water-insoluble azo dyes Es it has been found that valuable water-insoluble azo dyes are obtained can if you unsulfonated the diazo compounds of aromatic or heterocyclic Amines or their derivatives with the arylides of the o-oxynaphthocarbazole carboxylic acids for itself or on the fiber. The most varied of dyes are obtained in this way Shades which, produced on the fiber, have excellent fastness properties.

Beispiele Das gut ausgekochte und getrocknete Baumwollgarn wird mit einer Lösung von 3,8 g 5 - Oxy-cc-naphthocarbazol-6-carbonsäur e-o-toluidid, 2o ccm Natronlauge von 3411 Be, 25 cem Türkischrotöl im Liter imprägniert, ausgewunden, und, ohne zu trocknen, in einer mit Acetat abgestumpften Diazolösung, die 2 g 2 # 5-Dichloranilin im Liter enthält, entwickelt, gespült und geseift. Man erhält auf diese Weise ein schönes, echtes gelbstichiges Isatechu.Examples The well-boiled and dried cotton yarn is used with a solution of 3.8 g of 5 - oxy-cc-naphthocarbazole-6-carboxylic acid e-o-toluidide, 2o ccm caustic soda of 3411 Be, 25 cem Turkish red oil per liter impregnated, wound, and, without drying, in a diazo solution blunted with acetate, the 2 g of 2 # 5-dichloroaniline per liter contains, developed, rinsed and soaped. You get in this way a beautiful, real yellowish Isatechu.

Die in dieser Erfindung erwähnten Oxynaphthocarbazolcarbonsäuren sind nach Patent 51442o erhältlich.The oxynaphthocarbazole carboxylic acids mentioned in this invention are available under patent 51442o.

Nachstehend werden einige weitere Farbstoffe nebst ihren Farbtönen angeführt, die ebenso wie in dem Beispiel hergestellt wurden. Das 5-Oxy-a-naphthocarbazol-6-carbonsäure-o-toluidid von der Formel gibt mit dianotiertem 5-Nitro-2-anisidin von der Formel ein Schwarzbraun und mit dianotiertem 5-Chlor-2-toluidin von der Formel ein rotstichiges Katechu.A few other dyes are listed below along with their color shades, which were produced in the same way as in the example. The 5-oxy-a-naphthocarbazole-6-carboxylic acid-o-toluidide of the formula gives with dianotized 5-nitro-2-anisidine of the formula a black-brown and dianotized 5-chloro-2-toluidine of the formula a reddish catechu.

Die Arylide aus anderen o-Oxynaphthocarbazolcarbonsäuren ergeben ähnliche Farbtöne. Das 7-Oxy-a-naplitliocarbazol-6-carbonsäure-o-toluidid von der Formel gibt mit dianotiertem 5-Nitro-2-anisidin ein blaustichiges Schwarz, 5-Chlor-2-toluidin ein violettes Braun.The arylides from other o-oxynaphthocarbazole carboxylic acids give similar hues. The 7-oxy-a-naplitliocarbazole-6-carboxylic acid-o-toluidide of the formula gives a bluish black with dianotized 5-nitro-2-anisidine, 5-chloro-2-toluidine a purple brown.

Das 7-Oxy-a-naphthocarbazol-6-carbonsäure-ß-naphthalid gibt mit dianotiertem 5-Nitro-a-anisidin ein rotstickiges Schwarz, 5-Chlor-2-toluidin ein rotstickiges Braun.The 7-oxy-a-naphthocarbazole-6-carboxylic acid-ß-naphthalide gives with dianotized 5-Nitro-a-anisidine is black, 5-chloro-2-toluidine is red Brown.

Das 7-Oxv-o,-naphthocarbazol-6-oxycarbonsäure-p-toluididgibt mit dianotiertem 5-Vitro-2-anisidin ein grünstickiges Schwarz.The 7-Oxv-o, -naphthocarbazole-6-oxycarboxylic acid-p-toluidide gives with dianotized 5-Vitro-2-anisidine is a greenish black.

Das N-Methyl-7-oxy-cc-naphthocarbazol-6-carbonsäureanilid von der Formel gibt mit dianotiertem 5-1Titro-2-anisidin ein Schwarzbraun, 2 - 5-Dichloranilin ein Rotbraun.The N-methyl-7-oxy-cc-naphthocarbazole-6-carboxylic acid anilide of the formula gives a black-brown with dianotated 5-1-nitro-2-anisidine, 2-5-dichloroaniline a red-brown.

Das 3'-Methyl-7-oxy-a-naphthocarbazol-6-carbonsäureanilid von der Formel gibt mit dianotiertem 5-Nitro-2-anisidin ein grünstickiges Schwarz.The 3'-methyl-7-oxy-a-naphthocarbazole-6-carboxylic acid anilide of the formula gives a greenish black with dianotized 5-nitro-2-anisidine.

Das 7-Oxy-a-naphthocarbazol-6-carbonsäure-p-anisidid gibt mit dianotiertem 2-Aminocarbazol ein rotstickiges Schwarz, 2-Amino-7-äthoxyfluorenon ein blaustichiges Schwarz.The 7-oxy-a-naphthocarbazole-6-carboxylic acid-p-anisidide gives with dianotized 2-aminocarbazole has a red-tinged black, 2-amino-7-ethoxyfluorenone has a bluish tint Black.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung wasserunlöslicher Azofarbstoffe, darin bestehend, daß man Diazoverbindungen von aromatischen oder heterocyclischen Aminen oder ihren Derivaten für sich oder auf der Faser mit den Aryliden der o-Oxyriaphthocarbazolcarbonsäuren kuppelt.PATENT CLAIM: Process for the preparation of water-insoluble azo dyes, consisting in that one diazo compounds of aromatic or heterocyclic Amines or their derivatives by themselves or on the fiber with the arylides of the o-oxyriaphthocarbazole carboxylic acids clutch.
DEI39034D 1929-08-20 1929-08-20 Process for the preparation of water-insoluble azo dyes Expired DE539116C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEI39034D DE539116C (en) 1929-08-20 1929-08-20 Process for the preparation of water-insoluble azo dyes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEI39034D DE539116C (en) 1929-08-20 1929-08-20 Process for the preparation of water-insoluble azo dyes

Publications (1)

Publication Number Publication Date
DE539116C true DE539116C (en) 1931-11-21

Family

ID=7189953

Family Applications (1)

Application Number Title Priority Date Filing Date
DEI39034D Expired DE539116C (en) 1929-08-20 1929-08-20 Process for the preparation of water-insoluble azo dyes

Country Status (1)

Country Link
DE (1) DE539116C (en)

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