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DE744304C - Process for the preparation of asymmetrical disazo dyes - Google Patents

Process for the preparation of asymmetrical disazo dyes

Info

Publication number
DE744304C
DE744304C DEI68114D DEI0068114D DE744304C DE 744304 C DE744304 C DE 744304C DE I68114 D DEI68114 D DE I68114D DE I0068114 D DEI0068114 D DE I0068114D DE 744304 C DE744304 C DE 744304C
Authority
DE
Germany
Prior art keywords
sulfonic acid
disazo dyes
preparation
dyes
acid
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
DEI68114D
Other languages
German (de)
Inventor
Dr Eberhard Stein
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 DEI68114D priority Critical patent/DE744304C/en
Application granted granted Critical
Publication of DE744304C publication Critical patent/DE744304C/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
    • C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
    • C09B35/02—Disazo dyes
    • C09B35/039—Disazo dyes characterised by the tetrazo component
    • C09B35/08—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl
    • C09B35/10—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl from two coupling components of the same type
    • C09B35/16—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl from two coupling components of the same type from hydroxy-amines
    • 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
    • C09B45/24—Disazo or polyazo compounds
    • C09B45/28—Disazo or polyazo compounds containing copper

Landscapes

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

Description

Verfahren zur Herstellung unsymmetrischer Disazofarbstoffe Die vorliegende Erfindung betrifft ein Ver- fahren zur Herstellung von unsymmetrischen Disazofarbstoffen. Das Verfahren besteht darin, daß man tetrazotierte q., q.'-Diamino- diphenyl-3, 3'-dioxyessigsäure in beliebiger Reihenfolge mit i 11o1 - Aniitio-8-oxynaph- thalin-6-sulfortsätir@@ und i Mol einer 2-Arvl- ainino-8-oxynaplitlialin-6-sulfonsiiure, deren Arylrest zwei direkt miteinander verknüpfte Benzolkerne enthält, nacheinander kuppelt. Die neuen Farbstoffe färben natürliche und regenerierte- Cellulose in grauenTönen. Durch Nachbehandlung der Färbungen mit inetall- abgeben:den Mitteln, insbesondere mit Kupfer- salzen, «-erden die Echtheiten der Färbungen verbessert. Die nach,gel-Zupferteti Färbungen sind entsprechenden Färbungen mit bekann- ten, jedoch symmetrischen Farbstoffen bei teilweise besserer Lichtechtheit in der Wasch- echtheit überlegen. Beispiel In die mit Natriumbicarbonat neutralisierte svässer ige Tetrazolösung von 0,029 Mol ..1, q.'-Diaminodiphenyl-3, 3'-dioxyessigsätire, zu deren Herstellung 4Gewichtsteile Natrium- nitrit erforderlich sind, läßt man bei o° die wässerige Lösung von 7,56 Gewichtsteilen z-amino-8-oxynaphthalin-6-sulfonsaurem Na- trium einlaufen. Wenn keine freie Tetrazo- verbindu,ng mehr nachweisbar ist, läßt man ,las Gemisch, welches den halbseitig gekuppel- ten Farbstoff enthält, in eine stark ammo- niakalische Lösung von 0,03 Mol 2-Benzidino- 8-oxynaplithalin-(i-sulfonsäure bei o° ein- fließen und kuppelt längere Zeit, zum Schluß bei Raumtemperatur. Der fertige Farbstoff wird abgesaugt und -trocknet. Er stellt ein dunkles, metallisch glänzendes Pulver dar, das sich in Wasser mit blaugrauer Farbe löst und Baumwolle grau färbt. Beim Nachbehati- deln der Färbung mit Kupfersalzen erhält man ein rotstickiges Grau mit guter `i%asch- ünd Lichtechtheit. Farbstoffe mit ähnlichen Farbtönen werden erhalten, wenn man die 2-Benzidino-8-oxv- tiaphtlialin-f@-sulfonsäure durch die nach dem Bucherer-Verfahren aus 2, 4, 4.'-Triamino- dipheny 1 oder 2 Aminocarbazol und ?, 8-Di- oxynaplithalin - 6 - sulfonsäure erbältlichen :ipplungskomponenten ersetzt. Process for the preparation of asymmetrical disazo dyes The present invention relates to a drive to the production of unbalanced Disazo dyes. The procedure persists in that one tetrazotized q., q .'-diamino diphenyl-3, 3'-dioxyacetic acid in any Sequence with i 11o1 - Aniitio-8-oxynaph- thalin-6-sulfortsätir @@ and i mole of a 2-arvl- ainino-8-oxynaplitlialin-6-sulfonic acid, its Aryl radical two linked directly to one another Contains benzene nuclei, couples one after the other. The new dyes color natural and regenerated cellulose in gray tones. By Post-treatment of the dyeings with inetall- submit: the means, especially with copper salt, earth the fastness of the dyeings improved. The after, gel-Zupferteti stains are corresponding colors with known ten, but symmetrical dyes partially better lightfastness in the washing authenticity superior. example In the neutralized with sodium bicarbonate aqueous tetrazo solution of 0.029 mol ..1, q .'-Diaminodiphenyl-3, 3'-dioxyessigsätire, for their production 4 parts by weight of sodium nitrite are required, one leaves at o ° die aqueous solution of 7.56 parts by weight z-amino-8-oxynaphthalene-6-sulfonic acid Na- run in trium. If there is no free tetrazo connection is more detectable, one leaves , read the mixture, which contains the one-sided th dye, in a strongly ammo alkaline solution of 0.03 mol of 2-benzidino- 8-oxynaplithalin- (i-sulfonic acid at o ° flow and couple for a long time, at the end at room temperature. The finished dye is sucked off and dried. He's hiring dark, metallic shimmering powder, which dissolves in water with a blue-gray color and dyes cotton gray. When post-treatment deln the coloring with copper salts you get a red sticky gray with good `` i% ash- and lightfastness. Dyes with similar hues will be obtained by using the 2-benzidino-8-oxv- tiaphtlialin-f @ -sulfonic acid by the after Bucherer process from 2, 4, 4 .'- triamino- dipheny 1 or 2 aminocarbazole and?, 8-di- oxynaplithalin - 6 - sulfonic acid hereditary : ipplungsteile replaced.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung uns_vmmetri- scher Disazofarbstoffe, dadiireli gekenn- ;eiciiti(-t, daß man i 11o1 tetrazotierte I)iaminodiplienvl - 3, 3'- dioxyessig- säure in beliebiger Reikeiifolge mit i Mol 2 Atnino-8-oxynapbthalin-O-sulfonsäure und i 1M1 einer 2-.Arvlamino-8-oxynapli- thalin-6-sulfonsäure, deren Arvlrest zwei direkt miteinander verknüpfte Benzolkerne enthält, nacheinander kuppelt.
Zur Abgrenzung des Anmeldungsgegen- standes vom Stand der Technik sind im Ertei- lungsverfahren folgende Druckschriften in Be- tracht gezogen worden: französische Patentschrift . .. Nr. 818 154; USA.-Patentschrift . . . . . . . - 1861917; deutsche Patentschrift ... .. - 1()722(), h.1. 22 a, Gr. B.
PATENT CLAIM: Method of manufacturing us_vmmetri- scher disazo dyes, dadiireli marked ; eiciiti (-t that i 11o1 was tetrazotized I) iaminodiplienvl - 3, 3'- dioxyacetic- acid in any order with 1 mol 2 Atnino-8-oxynapbthalene-O-sulfonic acid and i 1M1 of a 2-arvlamino-8-oxynapli- thalin-6-sulfonic acid, the residue of which is two directly linked benzene nuclei contains, successively couples.
To delimit the registration object state of the art are in the the following publications in costume has been drawn: French patent specification. .. No. 818 154; U.S. Patent. . . . . . . - 1,861,917; German patent specification ... .. - 1 () 722 (), h.1. 22 a, size. B.
DEI68114D 1940-10-27 1940-10-27 Process for the preparation of asymmetrical disazo dyes Expired DE744304C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEI68114D DE744304C (en) 1940-10-27 1940-10-27 Process for the preparation of asymmetrical disazo dyes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEI68114D DE744304C (en) 1940-10-27 1940-10-27 Process for the preparation of asymmetrical disazo dyes

Publications (1)

Publication Number Publication Date
DE744304C true DE744304C (en) 1944-06-13

Family

ID=7196831

Family Applications (1)

Application Number Title Priority Date Filing Date
DEI68114D Expired DE744304C (en) 1940-10-27 1940-10-27 Process for the preparation of asymmetrical disazo dyes

Country Status (1)

Country Link
DE (1) DE744304C (en)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1861917A (en) * 1929-06-03 1932-06-07 Gen Aniline Works Inc Azodyestuffs containing copper
DE607226C (en) * 1932-02-18 1934-12-19 Chemische Ind Ges Process for the production of azo dyes
FR818154A (en) * 1936-02-21 1937-09-20 Ig Farbenindustrie Ag Azo dyes and their production process

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1861917A (en) * 1929-06-03 1932-06-07 Gen Aniline Works Inc Azodyestuffs containing copper
DE607226C (en) * 1932-02-18 1934-12-19 Chemische Ind Ges Process for the production of azo dyes
FR818154A (en) * 1936-02-21 1937-09-20 Ig Farbenindustrie Ag Azo dyes and their production process

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