DE807290C - Process for the preparation of monoazo dyes - Google Patents

Process for the preparation of monoazo dyes

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Publication number
DE807290C
DE807290C DEP34363A DEP0034363A DE807290C DE 807290 C DE807290 C DE 807290C DE P34363 A DEP34363 A DE P34363A DE P0034363 A DEP0034363 A DE P0034363A DE 807290 C DE807290 C DE 807290C
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oxy
nitro
amino
brown
benzene
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DEP34363A
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German (de)
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Dr Reinhard Neier
Dr Walter Wehli
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Sandoz AG
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Sandoz AG
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    • 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
    • C09B45/14—Monoazo compounds
    • C09B45/16—Monoazo compounds containing chromium

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

Description

Verfahren zur Herstellung von Monoazofarbstoffen Es wurde gefunden, daß man zu wertvollen Mono- azofarbstoffen dadurch gelangt, daß man diazotierte i-Oxy-2-amino-4-nitro-6-acylaminobenzole mit i-Oxy-2-acylamino-4-alkyl- bz«-. -cycloalkyl- 1>zw. -arylbenzolen kuppelt. Als Diazokomponenten können beispielsweise ver- wendet werden: i-Oxy-2-amino-4-nitro-6-formyl- aminobenzol, i-Oxy-2-amino-4-nitro-6-acetyl- aminobenzol, i-Oxy-2-amino-4-nitro-6-chloracetyl- aminobenzol, i-Oxy-2-amino-4-nitro-6-propionyl- aminobenzol, i-Oxy-2-amino-4-nitro-6-butyryl- aminobenzol, i-Oxy-2-amino-4-nitro-6-oxalylami- nobenzol, i-Oxy-2-amino-4-nitro-6-äthoxycarboyl- aminobenzol, i-Oxy-2-amino-4-nitro-6-methoxy- carboylaminobenzol, i-Oxy-2-amino-4-nitro-6-(f- äthoxy-äthoxy-carboylamino) -benzol, i -Oxy-2- amino-4-nitro-6-benzoylaminobenzol, i-Oxy-2- amino -4 - nitro - 6 - (3'- sulfobenzoyl) - aminobenzol, i -Oxy-2-amino-4-nitro- 6 - benzoylaminobenzol-2'-carbonsäure.Process for the preparation of monoazo dyes It has been found that valuable mono- azo dyes obtained by diazotizing i-Oxy-2-amino-4-nitro-6-acylaminobenzenes with i-Oxy-2-acylamino-4-alkyl- bz «-. -cycloalkyl- 1> betw. -arylbenzenes. As diazo components, for example, used: i-Oxy-2-amino-4-nitro-6-formyl- aminobenzene, i-oxy-2-amino-4-nitro-6-acetyl- aminobenzene, i-oxy-2-amino-4-nitro-6-chloroacetyl- aminobenzene, i-oxy-2-amino-4-nitro-6-propionyl- aminobenzene, i-oxy-2-amino-4-nitro-6-butyryl- aminobenzene, i-oxy-2-amino-4-nitro-6-oxalylami- nobenzene, i-oxy-2-amino-4-nitro-6-ethoxycarboyl- aminobenzene, i-oxy-2-amino-4-nitro-6-methoxy- carboylaminobenzene, i-oxy-2-amino-4-nitro-6- (f- ethoxy-ethoxy-carboylamino) -benzene, i -oxy-2- amino-4-nitro-6-benzoylaminobenzene, i-oxy-2- amino -4 - nitro - 6 - (3'-sulfobenzoyl) - aminobenzene, i -Oxy-2-amino-4-nitro-6-benzoylaminobenzene-2'-carboxylic acid.

Von diesen Verbindungen wurde bis jetzt einzig i-Oxy-2-ainino-4-nitro-6-acetylaminobenzol in der Literatur erwähnt, welches nach der Patentschrift 161 341 lierstellbar ist. Danach wird in i-Oxy-2-acetylamino-.4. 6-dinitrobenzol der zur Hydroxylgruppe o-ständige N itrosubstituent mit Schwefelalkalien zum Amin reduziert. Analog lassen sich die anderen der obenerwähnten Diazokomponenten herstellen, wobei Reduktionszeit, Temperatur und Alkalinität so gewählt werden müssen, daß keine Verseifung der Acylamingruppe eintritt.Of these compounds, only i-Oxy-2-ainino-4-nitro-6-acetylaminobenzene has so far been used mentioned in the literature, which can be produced according to patent specification 161,341. Then in i-Oxy-2-acetylamino-.4. 6-dinitrobenzene is the o-position to the hydroxyl group N itrosubstituent reduced with sulfur alkalis to the amine. The produce other of the above-mentioned diazo components, with reduction time, temperature and alkalinity must be chosen so that no saponification of the acylamine group entry.

Die i-Oxy-2-acylamino-4, 6-dinitrobenzolderivate lassen sich durch Einwirken der entsprechenden Säureanhydride, Säurechloride oder Säuren aus i-Oxy-2-amino-4.6-dinitrobenzol oder durch Nitrieren von i-OXV-2-acvlaminolienzol oder i-Oxv-2-acylatnino -4-nitrobenzol in konzentrierterSchwefelsäure bei tiefer Temperatur gewinnen.The i-oxy-2-acylamino-4, 6-dinitrobenzene derivatives can be passed through Action of the corresponding acid anhydrides, acid chlorides or acids from i-oxy-2-amino-4,6-dinitrobenzene or by nitrating i-OXV-2-acvlaminolienzol or i-Oxv-2-acylatnino -4-nitrobenzene in concentrated sulfuric acid at low temperature.

.-11s Azokomponenten können beispielsweise verwendet werden: 1-Oxy-2-acetylamino-4-metlivlbenzol, 1 -Oxy-2-formylamino-4-methvlbenzol, 1-Oxy-2-propionylamino-4-methylbenzol, 1-Oxy-2-t)tity-rylamino-4-tnethylbenzol, 1-Oxy-4-methy#1-2-1)ellzovlaminobenzol-2'-carbonsäure, 1-Oxy-2-benzoylamino-4-methyll)enzol, 1-Oxy-2-(3'-sulfobenzoy-1)-amino-4-metliylbenzol, ferner die entsprechenden Verbindungen, welche an Stelle der llethylgruppe in 4-Stellung höhere Alkvlreste, Cycloalkyl-oder Arvlreste, wie den Äthyl-, n-Propyl-, Isopropyl-, n-Butyl-, Isobutyl-, tert.-Butvl-, n-Amyl-, sek.-:@myl-, tert.-Amyl-, Isooctyl-, Cvclohexy 1- oder den, gegebenenfalls substituierten, Phenylrest, tragen..-11s azo components can be used, for example: 1-oxy-2-acetylamino-4-methylbenzene, 1-oxy-2-formylamino-4-methylbenzene, 1-oxy-2-propionylamino-4-methylbenzene, 1-oxy-2-t) tity-rylamino-4-methylbenzene, 1-Oxy-4-methy # 1-2-1) ellzovlaminobenzene-2'-carboxylic acid, 1-oxy-2-benzoylamino-4-methyll) enzene, 1-Oxy-2- (3'-sulfobenzoy-1) -amino-4-methylbenzene, also the corresponding compounds, which, instead of the methyl group in the 4-position, are higher alkyl radicals, cycloalkyl or Arvlreste, such as the ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-amyl-, sec .-: @ myl-, tert-amyl-, isooctyl-, cyclohexy 1- or den, optionally substituted phenyl radical.

Die Kupplung kann gegebelienfalls unter Zusatz von Pyridin ausgeführt werden.The coupling can optionally be carried out with the addition of pyridine will.

Die so erhältlichen Monoazofarbstoffe geben auf \Volle in chromierter Färbung volle braune Töne von sehr guten Echtheitseigenschaften. Die meisten von ihnen eignen sich auch gut für (las neutrale Einbadchromverfahren. Die Lichtechtheit und die \aßechtheiten sind meist vorzüglich.The monoazo dyes obtainable in this way give up \ Volle in chromed Dyeing full brown shades with very good fastness properties. Most of they are also well suited for (las neutral single-bath chrome process. The lightfastness and the fastnesses are mostly excellent.

Gegenüber den aus der schweizerischen Patenschrift 1966-53 tind deren Zusatzpatenten bekanntgewordenen Farbstoffen besitzen die Farbstoffe der vorliegenden Erfindung den Vorzug, teilweise besserer Lichtechtheit und teilweise besserer Naßechtlicit(,11. Beispiel 1 27,3 Teile 1-Oxy-2-amino-4-nitro-6-betizoylaminobenzol werden alkalisch gelöst, mit 6,9 Teilen \atriumnitrit und 3o Teilen Salzsäure indirekt dianotiert, und die Diazoverbindung wird mit t6,3 Teilen 1-Oxv-2-acetylamino-4-methvll)enzol in Gegenwart von Pyridin gekuppelt. Der isolierte und getrocknete @Ionoazofarl)stoff stellt ein dunkles Pulver dar, «-elches Wolle aus saurem Bad in rotbraunen Tönen färbt, die beim \achchromieren in ein dunkles Braun übergehen. Der Farbstoff eignet sich vorzüglich zum Färben von Wolle nach dem Einbadchromverfahren. Beispiele 21,1 Teile 1-Oxy-2-amino-4-nitro-6-acetylaminobenzol werden mit 6,9 Teilen \atriumnitrit und 22 Teilen Salzsäure dianotiert, und die Diazoverbindung wird mit 22,7 Teilen 1-Oxy-2-bCnzoylamino-4-tnethyll)enzol in Gegenwart von Py ridin gekuppelt. Der isolierte und getrocknete Monoazofarbstofi stellt ein dunkles Pulver dar, welches Wolle aus saurem Bad in rotbraunen Tönen färbt, die beim Nachchromieren in ein dunkles Braun umschlagen. Der Monoazofarbstoff eignet sich vorzüglich zum Färben von Wolle nach dem Einbadchromverfahren. Beisl)iel 3 24,1 Teile 1-Oxy-2-atnino-4-nitro-6-äthoxycarboylaminol)enzol werden alkalisch gelöst und mit 6,9 Teilen Natriumnitrit und 3o Teilen Salzsäure indirekt dianotiert, und die Diazoverbindung wird mit 22,7 Teilen 1-Oxy-2-1)etizoylamino-4-methylbenzol in Gegenwart von Pyridin gekuppelt. Der isolierte und getrocknete llonoazofarbstoff stellt ein dunkles Pulver dar, welches aus saurem Bade `Volle in rotbraunen Tönen färbt, die beim Nachchromieren in ein dunkles Braun- umschlagen. Er eignet sich auch gut zum Färben von Wolle nach dem Einbadchromverfahren.Compared to those from the Swiss patent specification 1966-53 there are theirs Additional patents known dyes have the dyes of the present Invention the advantage, partly better lightfastness and partly better wet fastness (11. Example 1 27.3 parts of 1-oxy-2-amino-4-nitro-6-betizoylaminobenzene become alkaline dissolved, indirectly dianotized with 6.9 parts of \ atrium nitrite and 3o parts of hydrochloric acid, and the diazo compound is treated with 6.3 parts of 1-oxv-2-acetylamino-4-methvll) enzene coupled in the presence of pyridine. The isolated and dried @Ionoazofarl) fabric represents a dark powder, "-moose wool from an acid bath in red-brown tones colors that turn into a dark brown when chromium plating. The dye is suitable excellent for dyeing wool using the single-bath chrome process. Examples 21.1 Parts of 1-oxy-2-amino-4-nitro-6-acetylaminobenzene are mixed with 6.9 parts of \ atrium nitrite and 22 parts of hydrochloric acid, and the diazo compound is dianotized with 22.7 parts 1-Oxy-2-bCnzoylamino-4-methylethyl) enzene coupled in the presence of pyridine. The isolated one and dried monoazo dye is a dark powder made from wool acidic bath in red-brown tones, which turns into a dark brown when re-chrome-plating turn over. The monoazo dye is particularly suitable for dyeing wool the single bath chrome process. Example 3 24.1 parts of 1-oxy-2-atnino-4-nitro-6-ethoxycarboylaminol) enzene are dissolved under alkaline conditions and treated with 6.9 parts of sodium nitrite and 3o parts of hydrochloric acid indirectly dianotized, and the diazo compound is mixed with 22.7 parts of 1-oxy-2-1) etizoylamino-4-methylbenzene coupled in the presence of pyridine. The isolated and dried ionoazo dye represents a dark powder, which from acid bath `Volle in red-brown tones colors that turn into a dark brown when chromium plating. He is suitable Also good for dyeing wool using the single bath chrome process.

Weitere Beispiele finden sich in der folgenden Zusammenstellung: Farbton der Diazokomponente Azokomponente nachchromierten Färbung auf Wolle 1-Oxv-2-amino-4-tiitro-6-acetylaniino- 1-Oxy-2-acetylamitio-4-methyll)elizol braun Benzol 1-Oxv-2-amitio-4-nitro-6-acetylamino- 1-Oxy-2-formylamino-4-methyli)enzol braun Benzol 1-()xv-2-atnitio-4-tiitro-6-acetylamino- 1-Oxy-2-propionylamino-4-methvlhenzol braun Benzol 1-Oxv-2-amitio-4-tiitro-6-acetylamitio- 1-Oxv-2-1)utvrvlaniino-4-metlivll)enzol braun bellzol 1-Oxv-2-aniitio-4-tiitro-6-acet_vlamitio- 1-OxN,-4-methyl-2-benzoylarriinol)etizol- dunkelbraun Benzol 2'-carbonsäure 1-()xv-2-amino-4-nitro-6-acetvlamino- 1-Oxv-2-(3'-sulfobetizoyl)-amino-4-metli_vl- dunkelbraun Benzol Benzol 1-Oxy--2-amit1o-4-nitro-6-acetylamino- 1-Oxy-2-acetvlamino-4-cyclollexvlbenzol braun Benzol 1-Oxv-2-amino-4-nitro-6-acetylamino- 1-Oxy-2-acetylamino-4-phenylbetizol braun Benzol 1-Oxy--2-amino-4-nitro-6-acetylamino- 1-Oxy-2-acetylamino-4-tert.-butyll)enzol braun Benzol 1-Oxy-2-amino-4-nitro-6-acetylamino- 1-Oxy-2-acetylamino-4-tert.-amylbenzol braun Benzol Farbton der Diazokomponente Azokomponente nachchromierten Färbung auf Wolle 1-Oxy-2-ainino-4-nitro-6-fornivlamino- 1-Ox@'-2-acet#, -lamino-4-niethyll)enzol braun Benzol I-Oxy-2-amiiio--j-iiitro-6-formylamino- 1-Oxy-2-l)etizo@-lamino-4-methylbenzol dunkelbraun Benzol 1-Oxy-2-amilio-4-nitro-6-forni\-lalnilio- i-Ox@-2-acet@-laniino-4-tert.-ltutvll)enzol braun Benzol I-Oxy-2-aniino-4-nitro-6-cliloracetylatnitio- i-Ox@--2-acet@-laniitio-4-methyll)enzol braun Benzol I-Oxy-2-amitlo-4-Ilitro-6-propionylatnino- i-Ox\--2-acet\-larnino-4-niethylbenzol braute Benzol 1-Oxy-2-ainino-4-tiitro-6-1)ropiotiylamino- 1-()xy-2-acetylanlino-4-tert.-butvll)enzol braun Benzol 1-Oxy-2-amino-4-nitro-6-1>utvrylamino- 1-Oxy-2-acet@lamino-4-methylbenzol braun Benzol 1-Oxy-2-amino-4-nitro-6-1>tityrylainino- i-Ox@-2-acetelaniino-4-tert.-ainyll)ei@. o1 braun Benzol 1-Oxy-2-amii1o-4-Ilitro-6-oxalylamino- 1-Oxy-2-acetylatnino-4-tert.-butyll)enzol braun Benzol 1-Oxy-2-ainino-4-nitro-6-oxalylamino- i-Oxy-2-1)enzoylaniilio-4-methylbenzol braun Benzol t-Oxy-2-amit1o-4-liitro-6-methoxycarlio_@l- 1-Oxy-2-acetylainifio-4-methylbenzol braun aminobenzol 1-Oxy-2-amino-4-nitro-6-inetlioxycarlioy1- i-Ox\--2-lienzoylamino-4-niethylberizol dunkelbraun aminobenzol I-Oxy-2-amino-4-nitro-6-äthoxycarl)oyl- i-Oxy-2-acetvlainino-4-Illetliyll)ellzol braun aminobenzol I-Oxy-2-aniino-4-nitro-6-(i3-ätlioxy- 1-()x@'--2-acetylainino-4-Inethylbenzol braun äthoxy-carboylamino)-1)enzol 1-Oxy-2-amino-4-nitro-6-benzovlamino- i-Oxy-2-fortil@-lamino-4-nietlivlbenzol braun Benzol 1-Oxy-2-amino-4-nitro-6-1>enzoylamino- I-Oxy-2-oxalelaniino-4-methylbenzol braun Benzol 1-Oxy-2-amino-4-niti-o-6-benzoyl-amino- 1-Oxy-2-acetylamino-4-methylbenzol braun benzol-2'-carl>oiisäure 1-Oxy-2-amino-4-nitro-6-ltenzoyl-aniino- 1-Oxy-2-acetylamino-4-tert.-butylbenzol braun benzol-2'-carbonsätire 1-Oxy-2-amino-4-nitro-(i-(3'-sulfo- i-Oxy-2-acetvlaniino-4-methelbenzol braun benzoyl) -aminobenzol I-Oxy-2-amino-4-nitro-(i-(3'-sulfo- I-Oxy-2-acetylamino-4-tert.-1)utylbenzol braun benzoyl)-aminobenzol 1-Oxy-2-amino-4-nitro-6-(3'-slllfo- 1-Oxy-2-benzoylamino-4-methylbenzol braun benzoyl)-aminol)enzol Further examples can be found in the following list: Hue of Diazo component Azo component re-chromed Coloring on Wool 1-Oxv-2-amino-4-thiitro-6-acetylaniino-1-Oxy-2-acetylamitio-4-methyll) elizol brown benzene 1-Oxv-2-amitio-4-nitro-6-acetylamino-1-Oxy-2-formylamino-4-methyli) enzene brown benzene 1 - () xv-2-atnitio-4-thiitro-6-acetylamino-1-oxy-2-propionylamino-4-methyenzene brown benzene 1-Oxv-2-amitio-4-tiitro-6-acetylamitio- 1-Oxv-2-1) utvrvlaniino-4-metlivll) enzene brown bellzol 1-Oxv-2-aniitio-4-tiitro-6-acet_vlamitio- 1-OxN, -4-methyl-2-benzoylarriinol) etizole- dark brown Benzene 2'-carboxylic acid 1 - () xv-2-amino-4-nitro-6-acetvlamino-1-Oxv-2- (3'-sulfobetizoyl) -amino-4-metli_vl- dark brown Benzene benzene 1-Oxy-2-amit1o-4-nitro-6-acetylamino-1-Oxy-2-acetylamino-4-cyclollexylbenzene brown benzene 1-Oxv-2-amino-4-nitro-6-acetylamino-1-Oxy-2-acetylamino-4-phenylbetizole brown benzene 1-Oxy-2-amino-4-nitro-6-acetylamino-1-oxy-2-acetylamino-4-tert-butyl) enzene brown benzene 1-Oxy-2-amino-4-nitro-6-acetylamino-1-oxy-2-acetylamino-4-tert-amylbenzene brown benzene Hue of Diazo component Azo component re-chromed Coloring on Wool 1-Oxy-2-ainino-4-nitro-6-fornivlamino-1-Ox @ '- 2-acet #, -lamino-4-niethyll) enzene brown benzene I-Oxy-2-amiiio - j-iiitro-6-formylamino-1-Oxy-2-l) etizo @ -lamino-4-methylbenzene dark brown benzene 1-Oxy-2-amilio-4-nitro-6-forni \ -lalnilio- i-Ox @ -2-acet @ -laniino-4-tert.-ltutvll) enzene brown benzene I-Oxy-2-aniino-4-nitro-6-cliloracetylatnitio- i-Ox @ - 2-acet @ -laniitio-4-methyll) enzene brown benzene I-Oxy-2-amitlo-4-Ilitro-6-propionylatnino-i-Ox \ - 2-acet \ -larnino-4-niethylbenzene brewed benzene 1-Oxy-2-ainino-4-tiitro-6-1) ropiotiylamino-1 - () xy-2-acetylanlino-4-tert.-butvll) enzene brown benzene 1-Oxy-2-amino-4-nitro-6-1> utvrylamino-1-Oxy-2-acet @ lamino-4-methylbenzene brown benzene 1-Oxy-2-amino-4-nitro-6-1> tityrylainino- i-Ox@-2-acetelaniino-4-tert.-ainyll) ei @. o1 brown benzene 1-Oxy-2-amii1o-4-Ilitro-6-oxalylamino-1-Oxy-2-acetylamino-4-tert-butyl) enzene brown benzene 1-Oxy-2-ainino-4-nitro-6-oxalylamino-i-Oxy-2-1) enzoylaniilio-4-methylbenzene brown benzene t-Oxy-2-amit1o-4-liitro-6-methoxycarlio_ @ l- 1-Oxy-2-acetylainifio-4-methylbenzene brown aminobenzene 1-Oxy-2-amino-4-nitro-6-inetlioxycarlioy1- i-Ox \ - 2-lienzoylamino-4-niethylberizole dark brown aminobenzene I-Oxy-2-amino-4-nitro-6-ethoxycarl) oyl- i-Oxy-2-acetvlainino-4-Illetliyll) ellzol brown aminobenzene I-Oxy-2-aniino-4-nitro-6- (i3-ätlioxy- 1 - () x @ '- 2-acetylainino-4-methylbenzene brown ethoxy-carboylamino) -1) enzene 1-Oxy-2-amino-4-nitro-6-benzovlamino-i-Oxy-2-fortil @ -lamino-4-nietlivlbenzene brown benzene 1-Oxy-2-amino-4-nitro-6-1> enzoylamino-I-Oxy-2-oxalelaniino-4-methylbenzene brown benzene 1-Oxy-2-amino-4-niti-o-6-benzoyl-amino-1-oxy-2-acetylamino-4-methylbenzene brown benzene-2'-carlic acid 1-Oxy-2-amino-4-nitro-6-ltenzoyl-aniino-1-oxy-2-acetylamino-4-tert.-butylbenzene brown benzene-2'-carbonates 1-Oxy-2-amino-4-nitro- (i- (3'-sulfo-i-Oxy-2-acetylaniino-4-methelfenzene brown benzoyl) aminobenzene I-oxy-2-amino-4-nitro- (i- (3'-sulfo-I-oxy-2-acetylamino-4-tert-1) utylbenzene brown benzoyl) aminobenzene 1-Oxy-2-amino-4-nitro-6- (3'-slllfo- 1-Oxy-2-benzoylamino-4-methylbenzene brown benzoyl) aminol) enzene

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von Monoazofarbstoffen, dadurch gekennzeichnet, daß man diazotierte I-Oxy-2-amino-4-nitro-6-acylaminobenzole mit I-Oxy-2-acylamino-4-alkyl- bzw. -cycloalkyl- bzw. -arylbenzolen kuppelt. PATENT CLAIM: Process for the preparation of monoazo dyes, characterized in that diazotized I-oxy-2-amino-4-nitro-6-acylaminobenzenes with I-oxy-2-acylamino-4-alkyl or -cycloalkyl- or - arylbenzenes.
DEP34363A 1948-02-18 1949-02-17 Process for the preparation of monoazo dyes Expired DE807290C (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE951946C (en) * 1954-05-09 1956-11-08 Bayer Ag Process for the production of o, o'-dioxyazo dyes or their metal complex compounds
DE1003375B (en) * 1954-03-25 1957-02-28 Bayer Ag Process for the production of monoazo dyes and their metal complex compounds
DE975671C (en) * 1941-05-10 1962-04-26 Aeg Electric circuit breaker with arc extinguishing by a self-generated extinguishing agent

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE975671C (en) * 1941-05-10 1962-04-26 Aeg Electric circuit breaker with arc extinguishing by a self-generated extinguishing agent
DE1003375B (en) * 1954-03-25 1957-02-28 Bayer Ag Process for the production of monoazo dyes and their metal complex compounds
DE951946C (en) * 1954-05-09 1956-11-08 Bayer Ag Process for the production of o, o'-dioxyazo dyes or their metal complex compounds

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