CH244514A - Process for the preparation of an azo dye. - Google Patents

Process for the preparation of an azo dye.

Info

Publication number
CH244514A
CH244514A CH244514DA CH244514A CH 244514 A CH244514 A CH 244514A CH 244514D A CH244514D A CH 244514DA CH 244514 A CH244514 A CH 244514A
Authority
CH
Switzerland
Prior art keywords
methyl
red
tetrazotized
orange
salicylic acid
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellschaft Ciba
Original Assignee
Ciba Geigy
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 Ciba Geigy filed Critical Ciba Geigy
Publication of CH244514A publication Critical patent/CH244514A/en

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
    • 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
    • C09B35/36—Trisazo dyes of the type
    • C09B35/366—D is diphenyl
    • 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
    • C09B35/38—Trisazo dyes ot the type

Landscapes

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

Description

  

  Verfahren zur Herstellung eines     Azofarbstoffes.       Es     wurde    gefunden, dass     ein    wertvoller       Azofarbstoff    hergestellt werden kann, wenn       nian        tetrazotiertes        3-Oxy-4,4'-diaminodiphenyl     einerseits mit     Salicylsäure    und anderseits mit       1-(3'        -PI-        Oxyäthoxyphenyl)    - 3     -methyl-5-pyr-          azolon    kuppelt.  



  Der neue Farbstoff stellt ein dunkles Pul  ver dar, das sich in Wasser mit     orangebrau-          ner,    in     verdünnten    Alkalien mit orangeroter  und in konzentrierter Schwefelsäure mit rubin  roter Farbe löst und pflanzliche Fasern nach  dem     einbadigen        Nachkupferungsverfahren        in     wasch- und lichtechten Rottönen färbt.  



  Die     Tetrazoh-erung    des     3-Ogybenzidins     kann in     bekannter    Weise z. B. in salzsaurer  Lösung     vorgenommen    werden. Die Kupplung  der     Tetrazoverbindung    mit den beiden     Azo-          komponenten    kann in alkalischem, z. B. Al  kalihydroxyd oder     -earbonat    enthaltendem  Medium durchgeführt werden und erfolgt  zweckmässig in zwei Stufen.     Hierbei        kann     man vorteilhaft die     Tetrazoverbindung    in  einer 1. Stufe mit     Salicylsäure    und in einer  2.

   Stufe mit     1-(3'-ss-Oxyäthoxyphenyl)-3-          methyl-5-pyrazolon    vereinigen.         Beispiel:     5,0 Teile     3-Oxybenzidin    werden in übli  cher Weise in Gegenwart von Salzsäure mit       Natriumnitrit        tetrazotiert.    Die Lösung der       Tetrazoverbindung    wird bei 5      mit    einer  Lösung von 3,

  5     Teilen        Salicylsäure    und 6  Teilen     Natriumhydroxyd    in<B>40</B> Teilen Wasser       vereinigt    und das     Gemisch    während     1/-    Stunde  bei 4-6      gerührt.    Nach dieser Zeit ist der       Monoazofarbstoff    gebildet. Man gibt     nun    zum       Kupplungsgemisch    eine Lösung von 5,85 Tei  len     1-(3'-ss-Oxyäthoxyphenyl)-3-methyl-5-          pyrazolon    und 2     Teilen        Natriumhydroxyd    in  50 Teilen Wasser.

   Man rührt das     Gemisch     während 1 Stunde bei 10-12  und 20 Stunden  bei 15-20 . Durch Zusatz von Kochsalz wird  der Farbstoff abgeschieden und getrocknet.



  Process for the preparation of an azo dye. It has been found that a valuable azo dye can be produced if nian tetrazotized 3-oxy-4,4'-diaminodiphenyl on the one hand with salicylic acid and on the other hand with 1- (3 '-PI-oxyethoxyphenyl) -3-methyl-5-pyr- azolon domes.



  The new dye is a dark powder that dissolves in water with an orange-brown color, in dilute alkalis with orange-red and in concentrated sulfuric acid with a ruby-red color and colors vegetable fibers in washable and light-fast red tones using the one-bath copper plating process.



  The Tetrazoh-erung of 3-Ogybenzidins can in a known manner, for. B. be made in hydrochloric acid solution. The coupling of the tetrazo compound with the two azo components can be carried out in an alkaline, e.g. B. Al kalihydroxyd or carbonate-containing medium are carried out and is conveniently carried out in two stages. Here you can advantageously use the tetrazo compound in a 1st stage with salicylic acid and in a 2nd stage.

   Combine stage with 1- (3'-ss-oxyethoxyphenyl) -3-methyl-5-pyrazolone. Example: 5.0 parts of 3-oxybenzidine are tetrazotized in the usual manner in the presence of hydrochloric acid with sodium nitrite. The solution of the tetrazo compound is at 5 with a solution of 3,

  5 parts of salicylic acid and 6 parts of sodium hydroxide are combined in 40 parts of water and the mixture is stirred at 4-6 for 1/1 hour. After this time the monoazo dye is formed. A solution of 5.85 parts of 1- (3'-ss-oxyethoxyphenyl) -3-methyl-5-pyrazolone and 2 parts of sodium hydroxide in 50 parts of water is then added to the coupling mixture.

   The mixture is stirred for 1 hour at 10-12 and 20 hours at 15-20. The dye is deposited by adding sodium chloride and dried.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines. Azofarb- stoffes, dadurch gekennzeichnet, dass man tetrazotiertes 3 - Oxy - 4,4' - diaminodiphenyl einerseits mit Salicy lsäure und anderseits mit 1-(3' -ss - Oxyäthoxyplienyl) - 3 - methyl- 5 -pyr- azolon kuppelt. PATENT CLAIM: Process for producing a. Azo dyes, characterized in that tetrazotized 3-oxy-4,4'-diaminodiphenyl is coupled with salicylic acid on the one hand and with 1- (3 '-ss-oxyethoxyplienyl) -3-methyl-5-pyrazolone on the other. Der neue Farbstoff stellt ein dunkles Pul ver dar, das sich in Wasser mit orangebrau- ner, in verdünnten Alkalien mit orangeroter und in konzentrierter Schwefelsäure mit rubinroter Farbe löst und pflanzliche Fasern nach dem einbadigen Nachkupferungsver- fahren in wasch- und lichtechten Rottönen färbt. The new dye is a dark powder that dissolves in water with an orange-brown color, in dilute alkalis with orange-red and in concentrated sulfuric acid with a ruby-red color and colors vegetable fibers in wash- and light-fast red tones using the one-bath copper plating process. UN TERAN SPRUCII Verfahren gemäss Patentanspruch, dadurch gekennzeichnet, dass man das tetrazotierte 3- Ox\T-4,4'-diaminodiphenyl zuerst mit Salicyl- säure und hierauf mit 1-(3'-fl-Oxyäthoxy- ph.eny 1)-3-methyl-ä-py ra.zolon vereinigt. UN TERAN SPRUCII process according to patent claim, characterized in that the tetrazotized 3-Ox \ T-4,4'-diaminodiphenyl is first treated with salicylic acid and then with 1- (3'-fl-Oxyäthoxy- ph.eny 1) - 3-methyl-a-py ra.zolon combined.
CH244514D 1942-09-03 1942-09-03 Process for the preparation of an azo dye. CH244514A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH244514T 1942-09-03
CH242160T 1946-04-30

Publications (1)

Publication Number Publication Date
CH244514A true CH244514A (en) 1946-09-15

Family

ID=25728656

Family Applications (3)

Application Number Title Priority Date Filing Date
CH242160D CH242160A (en) 1942-09-03 1942-09-03 Process for the preparation of an azo dye.
CH244514D CH244514A (en) 1942-09-03 1942-09-03 Process for the preparation of an azo dye.
CH244513D CH244513A (en) 1942-09-03 1942-09-03 Process for the preparation of an azo dye.

Family Applications Before (1)

Application Number Title Priority Date Filing Date
CH242160D CH242160A (en) 1942-09-03 1942-09-03 Process for the preparation of an azo dye.

Family Applications After (1)

Application Number Title Priority Date Filing Date
CH244513D CH244513A (en) 1942-09-03 1942-09-03 Process for the preparation of an azo dye.

Country Status (2)

Country Link
CH (3) CH242160A (en)
NL (1) NL60747C (en)

Also Published As

Publication number Publication date
CH244513A (en) 1946-09-15
NL60747C (en)
CH242160A (en) 1946-04-30

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