DE643081C - Process for the production of azo dyes - Google Patents

Process for the production of azo dyes

Info

Publication number
DE643081C
DE643081C DEI53332D DEI0053332D DE643081C DE 643081 C DE643081 C DE 643081C DE I53332 D DEI53332 D DE I53332D DE I0053332 D DEI0053332 D DE I0053332D DE 643081 C DE643081 C DE 643081C
Authority
DE
Germany
Prior art keywords
production
azo dyes
amino
parts
dyes
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
DEI53332D
Other languages
German (de)
Inventor
Dr Erich Baumann
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 DEI53332D priority Critical patent/DE643081C/en
Application granted granted Critical
Publication of DE643081C publication Critical patent/DE643081C/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
    • C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
    • C09B29/08—Amino benzenes
    • 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

Verfahren zur Herstellung von Azofarbstoffen Gegenstand des Patents 6.4o 5zi ist ein Verfahren zur Herstellung von insbesondere für das Färben von Celluloseestern geeigneten Azofarbstoffen, welches darin besteht, daß man die Diazoverbindungen aus i-Amino-2, 6-dih.alogen-4-nitrobenzolen mit i-Dioxalkylamino-3-halogenbenzolen, die keine weiteren Kernsubstituenten enthalten, kuppelt. Die Farbstoffe besitzen neben allgemeinen guten Eigenschaften besonders gute Lichtechtheit. Gegenstand des Patents 642 765 ist ein Verfahren zur Herstellung von für den ichen Zweck geeigneten, durch Kuppeln von diazotiertem i-Amino-4-nitrobenzol mit i -Dioxalkylamin-o-3-hal,ogenbenzolen, die keine weiteren Kernsubitituenten. enthalten, erhältlichen Azofarbstoffen, die ebenfalls gute Eigenschaften aufweisen.Process for the production of azo dyes The subject of the 6.4o 5zi patent is a process for the production of azo dyes particularly suitable for dyeing cellulose esters, which consists in that the diazo compounds are obtained from i-amino-2,6-dih.alogen-4-nitrobenzenes with i-Dioxalkylamino-3-halobenzenes, which contain no further core substituents, couples. In addition to generally good properties, the dyes have particularly good lightfastness. The subject of patent 642 765 is a process for the preparation of suitable for the purpose by coupling diazotized i-amino-4-nitrobenzene with i-dioxalkylamine-o-3-hal, ogenbenzenes, which have no further core substituents. contain, available azo dyes, which also have good properties.

Verwendet man nun an Stelle von diazotiert-em i-Amino-4-nitrDbenzol diazotierte i-Amin,o-2-halogen-4-nitrob-enzol,e zur Kupplung mit i-Dioxalkylamino-3-halogenbe-nzolen, die keine weiteren Kernsubstituenten. enthalten, so erhält man gleichfalls für die Acetatseidenfärberei sehr geeignete Farbstoffe von guten Echtheitseigenschaften.If one uses now instead of diazotized-em i-amino-4-nitrDbenzene diazotized i-amine, o-2-halo-4-nitrobenzene, e for coupling with i-dioxalkylamino-3-halobenzenes, which have no further core substituents. contained, one also obtains for the Acetate silk dyeing are very suitable dyes with good fastness properties.

Gegenüber dem bekannten Farbstoff aus diazotiertem i -Amino-2-chlor-4-nitrobenzol und i-Diaxäthylamino-3-methylbenzol besitzt der entsprechende, nach vorliegendem Verfahren erhältliche Farbstoff eine bessere Schwefelechtheit. Vor dem bekannten Farbstoff aus diazotiertem i-Amino-2-cWor-4-nitrobenzol und i-Dioxätliylami-no-3-chlor-6-methoxybenzol zeichnen sich die neuen Farbstoffe durch bessere Lichtechtheit und vor dem bekannten Farbstoff aus diazotiertem i-Amino-2-brom-4,6-dinitrobenzol und i-Dioxäthylamin#o-3-chlorbenzol durch wesentlich bessere Lichtechtheit aus. Beispiel i Eine aus 17,3 Teilen i-Amino-2-chlor-4-nitrobenzol auf dem üblichen Wege hergestellte Diazolösung läßt man in eine kalte Lösung g von 21,6 Teilen i-Dioxäthylamino-3-chl,orbenzol in 25 Teilen Salzsäure 23' B6 und 8oo Teilen Wasser fließen und stumpft zur Beendigung der Kupplung mit Natriumacetat ab. Der anfallende Farbstoff liefert auf Acetatseide blaustichige Rottön-e von guten Echtheitseigenschaften, insbesondere von vorzül-licher Lichtechtheit.Compared to the known dye made from diazotized i-amino-2-chloro-4-nitrobenzene and i-diaxäthylamino-3-methylbenzene, the corresponding dye obtainable by the present process has better resistance to sulfur. Before the known dye made from diazotized i-amino-2-cWor-4-nitrobenzene and i-Dioxätliylami-no-3-chloro-6-methoxybenzene, the new dyes are characterized by better lightfastness and from the known dye made from diazotized i-amino- 2-bromo-4,6-dinitrobenzene and i-dioxäthylamine # o-3-chlorobenzene are characterized by much better lightfastness. EXAMPLE i A diazo solution prepared in the usual way from 17.3 parts of i-amino-2-chloro-4-nitrobenzene is added to a cold solution of 21.6 parts of i-dioxäthylamino-3-chlorobenzene in 25 parts of hydrochloric acid 23 ' B6 and 800 parts of water flow and are blunted to complete the coupling with sodium acetate. The resulting dye gives blue-tinged red tones on acetate silk with good fastness properties, in particular excellent lightfastness.

Verwendet man i-Dioxäthylamino-3-brombenzol an Stelle von i-Dioxäthylami-no-3-chlorbenzol, so erhält man einen Farbstoff, der Acetatseide, ebenfalls in echten Rottönen färbt.If i-Dioxäthylamino-3-bromobenzene is used instead of i-Dioxäthylamino-3-chlorobenzene, in this way a dye is obtained that dyes acetate silk, also in real shades of red.

Beispiel 2 Eine in üblichier Weise aus 247 Teilen i-Ainino-2-brOm-4-nitrobenzol hergestellte Diazelösung fließt in eine kalte Lösung von I 21,6 Teilen i-Dioxäthylamino-3-chlorbenzol in 25 Teilen Salzsäure 23' B6 und 8oo Teilen Wasser. Der nach Beendigung der Kupplung durch Abstumpfen mit Natriumacetat anfallende Farbstoff färbt Acctats#eide in echt(-ii blauroten Tönen.Example 2 A diazo solution prepared in the usual way from 247 parts of i-amino-2-brom-4-nitrobenzene flows into a cold solution of 21.6 parts of i-dioxäthylamino-3-chlorobenzene in 25 parts of hydrochloric acid 23 ' B6 and 800 parts Water. After the coupling has ended, the dye obtained by blunting it with sodium acetate stains the acetate in real (-ii blue-red shades.

BeiVerwendung Von 26Teilen i-Dioxäthviamino-3-brombenzol erhält man einen Farb. stoff, der Acetatseide in ähnlichen Tönerr lärbt.If 26 parts of i-dioxäthviamino-3-bromobenzene are used, one obtains one color. fabric that dyes acetate silk in similar shades.

Claims (1)

PATrNTAINSPRUCH : \'erfahren zur Herstellung von Azo- farbstoffen, dadurch gekennzeichnet, daß man die Diazoverbindungen aus i-Amino- 2-halogen-.4-nitrol-#eiizolen mit i-Dioxalkyl- ainiiio-3-halogeiil>enzoleii, die keine wei- türen Kernsübstituenten enthalten, kuppelt.
PATRNTAIN CLAIM : \ 'experienced in the production of azo dyes, characterized in that the diazo compounds from i-amino 2-halogen-.4-nitrole- # eiizoles with i-dioxalkyl- ainiiio-3-halogeiil> enzoleii that have no Doors contain core substituents.
DEI53332D 1935-03-14 1935-03-14 Process for the production of azo dyes Expired DE643081C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEI53332D DE643081C (en) 1935-03-14 1935-03-14 Process for the production of azo dyes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEI53332D DE643081C (en) 1935-03-14 1935-03-14 Process for the production of azo dyes

Publications (1)

Publication Number Publication Date
DE643081C true DE643081C (en) 1937-03-24

Family

ID=7193578

Family Applications (1)

Application Number Title Priority Date Filing Date
DEI53332D Expired DE643081C (en) 1935-03-14 1935-03-14 Process for the production of azo dyes

Country Status (1)

Country Link
DE (1) DE643081C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6489287B1 (en) 1997-05-09 2002-12-03 Rohm And Haas Company Detergent formulations comprising at least one water soluble polymer, or salt thereof, bearing a phosphonate group

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6489287B1 (en) 1997-05-09 2002-12-03 Rohm And Haas Company Detergent formulations comprising at least one water soluble polymer, or salt thereof, bearing a phosphonate group

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