DE575216C - Process for the preparation of a monoazo dye - Google Patents

Process for the preparation of a monoazo dye

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Publication number
DE575216C
DE575216C DEI42529D DEI0042529D DE575216C DE 575216 C DE575216 C DE 575216C DE I42529 D DEI42529 D DE I42529D DE I0042529 D DEI0042529 D DE I0042529D DE 575216 C DE575216 C DE 575216C
Authority
DE
Germany
Prior art keywords
preparation
monoazo dye
solution
dye
methoxybenzene
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
DEI42529D
Other languages
German (de)
Inventor
Dr Wilhelm Lamberz
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 DEI42529D priority Critical patent/DE575216C/en
Application granted granted Critical
Publication of DE575216C publication Critical patent/DE575216C/en
Expired legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00Monoazo dyes prepared by diazotising and coupling
    • C09B29/10Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
    • C09B29/18Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides
    • C09B29/20Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides of the naphthalene series

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

Description

Verfahren zur Herstellung eines Monoazofarbstoffs Es wurde gefunden, daB man einen Monoazofarbstoff vom Farbton des Türkischrots dadurch erhält, daß man die Diazoverbindung des i-Amino-2-methoxybenzol-5-sulfonsäurediäthylamids mit i -(2' # 3'-Oxynaphthoylamino)-2 # 4-dimethoxy-5-chlorbenzol in Substanz oder auf der Faser kuppelt. Die auf der Faser hergestellte Färbung zeichnet sich durch gute Licht-, Wetter-, Chlor- und Natronlaugekochechtheit aus.Process for the preparation of a monoazo dye It has been found that a monoazo dye of the shade of Turkish red is obtained by the diazo compound of i-amino-2-methoxybenzene-5-sulfonic acid diethylamide with i - (2 ' # 3'-oxynaphthoylamino) -2 # 4-dimethoxy-5-chlorobenzene in substance or on the fiber couples. The dye produced on the fiber is distinguished by its good fastness to light, weather, chlorine and caustic soda.

Das bisher nicht beschriebene i Amino-2 - methoxybenzol - 5 - sulfonsäurediäthylamid kann in üblicher Weise durch Reduktion der entsprechenden Nitroverbindung erhalten werden. Monokline farblose Kristalle aus verdünntem Alkohol. F. 104 bis io5° C. Die Nitroverbindung ist durch Kondensation von i-Nitro-2-methoxybenzol-5-sulfonsäurechlorid mit Diäthylamin erhältlich; schwach gelb gefärbte prismatische Kristalle. F. 77 bis 78° C.The previously not described i-amino-2-methoxybenzene-5-sulfonic acid diethylamide can be obtained in the customary manner by reducing the corresponding nitro compound will. Monoclinic colorless crystals from dilute alcohol. F. 104 to io5 ° C. The nitro compound is formed by condensation of i-nitro-2-methoxybenzene-5-sulfonic acid chloride available with diethylamine; pale yellow colored prismatic crystals. F. 77 up to 78 ° C.

Beispiel -Herstellung des Farbstoffes auf der Faser Grundierungsbad 49 i-(2' # 3'-Oxynaphthoylamino)-2 # ¢-dimethoxy-5-chlorbenzol werden in einem Gemisch von 8 ccm denatuiertem Alkohol, 2 ccm Natronlauge 38' B8, 4 ccm Wasser, 4 ccm Knochenleimlösung i : io und 4 ccm Formaldehydlösung, 33prozentig, gelöst. Diese Lösung wird in etwa 1/Q 1 Wasser, das io ccm Natronlauge von 38° B6, 6 ccm Türkischrotöl und 2 g Knochenleim enthält, unter gutem Rühren eingegossen. Danach. wird auf i 1 eingestellt.Example - preparation of the dye on the fiber primer bath 49 i- (2 '# 3'-oxynaphthoylamino) -2 # ¢ -dimethoxy-5-chlorobenzene are mixed in a mixture of 8 cc of denatured alcohol, 2 cc of sodium hydroxide solution 38' B8, 4 cc Water, 4 cc bone glue solution i: 10 and 4 cc formaldehyde solution, 33 percent, dissolved. This solution is poured into about 1 / Q1 of water containing 10 cc of sodium hydroxide solution at 38 ° B6, 6 cc of Turkish red oil and 2 g of bone glue, with thorough stirring. Thereafter. is set to i 1.

Entwicklungsbad 2,6 g i-Amino-2-methoxybenzol-5-sulfonsäurediäthylamid werden mit 25 ccm warmem Wasser und 3 ccm Salzsäure von 20° B6 gelöst. Die Lösung wird auf'etwa 15° C abgekühlt. Dann werden 0,75 g Natriumnitrit (98prozentig) in Wasser gelöst und unter Rühren zugegeben. Nach etwa io Minuten wird die überschüssige Salzsäure mit essigsaurem Natrium abgestumpft. Darauf werden 50 g Kochsalz zugegeben, und die Lösung wird auf 1 1 eingestellt.Development bath 2.6 g of i-amino-2-methoxybenzene-5-sulfonic acid diethylamide are dissolved with 25 cc of warm water and 3 cc of hydrochloric acid at 20 ° B6. The solution is cooled to about 15 ° C. Then 0.75 g of sodium nitrite (98 percent) are dissolved in water and added with stirring. After about 10 minutes the excess hydrochloric acid is blunted with sodium acetate. Then 50 g of sodium chloride are added and the solution is adjusted to 1 liter.

Färbevorschrift 5o g abgekochtes Baumwollgarn werden 112 Stunde im Grundierungsbad bei etwa 3o' C behandelt und danach durch Abquetschen oder Auswinden möglichst von der überschüssigen Flüssigkeit befreit. Dann behandelt man % Stunde im Entwicklungsbad, spült, seift bei Kochtemperatur, spült wieder und trocknet. Man erhält eine klare Türkischrotfärbung, die hohe Lichtechtheit mit sehr guter Chlor-, Wasch-, Soda- und Natronlaugekochechtheit verbindet.Dyeing instructions 50 g of boiled cotton yarn are im 112 hours Treated primer bath at about 3o'C and then by squeezing or wringing out if possible freed from the excess liquid. Then you treat% hour in the developing bath, rinses, soaps at boiling temperature, rinses again and dries. A clear Turkish red color is obtained, the high lightfastness with very good fastness to chlorine, washing, soda and caustic soda.

Herstellung des Farbstoffs in Substanz 2,6 Gewichsteile i-Amino-2,methoxybenzol= 5-sulfonsäurediäthylamid werden in üblicher Weise diazotiert. Die Diazoverbindung wird mit 3,6Gewichtsteilen i- (2'- 3'-Oxynaphthoylamino)-2 # 4-dimethoxy-5-chlorbenzol gelöst in einer Lösung von verdünnter Natronlauge und Türkischrotöl, die mit der zur Bindung der überschüssigen Mineralsäure hinreichenden Menge Natriumacetat versetzt ist,' gekuppelt. Der aus der Lösung sich ausscheidende Farbstoff wird abfiltriert und gut ausgewaschen: Getrocknet stellt er ein rotes Pulver dar, das sich in konzentrierter Schwefelsäure mit rotvioletter Farbe löst.Preparation of the dye in substance 2.6 parts by weight of i-amino-2, methoxybenzene = 5-sulfonic acid diethylamide are diazotized in the usual way. The diazo compound is added with 3.6 parts by weight of i- (2'- 3'-Oxynaphthoylamino) -2 # 4-dimethoxy-5-chlorobenzene dissolved in a solution of dilute sodium hydroxide solution and turkey red oil, which is mixed with the Sufficient sodium acetate is added to bind the excess mineral acid is, 'coupled. The dye which separates out of the solution is filtered off and well washed out: when dry, it is a red powder that is concentrated in Dissolves sulfuric acid with a red-violet color.

Die daraus hergestellten klaren, blauroten Lacke sind ölecht und gut lichtecht.The clear, blue-red paints made from it are oil-poor and good lightfast.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Monoazofarbstoffes, dadurch gekennzeichnet, daB man diazotiertes i -Amino-2-methoxybenzol-5-sulfonsäurediäthylamid in Substanz oder auf der Faser mit i-(2' # 3'-Oxynaphthoylamino)-2 # q.-dimethoxy-5-chlorbenzol kuppelt. Claim: Process for the preparation of a monoazo dye, characterized in that diazotized i-amino-2-methoxybenzene-5-sulfonic acid diethylamide in substance or on the fiber with i- (2 '# 3'-oxynaphthoylamino) -2 # q.-dimethoxy -5-chlorobenzene couples.
DEI42529D 1931-09-09 1931-09-09 Process for the preparation of a monoazo dye Expired DE575216C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEI42529D DE575216C (en) 1931-09-09 1931-09-09 Process for the preparation of a monoazo dye

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEI42529D DE575216C (en) 1931-09-09 1931-09-09 Process for the preparation of a monoazo dye

Publications (1)

Publication Number Publication Date
DE575216C true DE575216C (en) 1933-04-26

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Family Applications (1)

Application Number Title Priority Date Filing Date
DEI42529D Expired DE575216C (en) 1931-09-09 1931-09-09 Process for the preparation of a monoazo dye

Country Status (1)

Country Link
DE (1) DE575216C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE965917C (en) * 1955-03-31 1957-06-27 Bayer Ag Process for the preparation of water-insoluble monoazo dyes

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE965917C (en) * 1955-03-31 1957-06-27 Bayer Ag Process for the preparation of water-insoluble monoazo dyes

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