CH257285A - Process for the preparation of a new monoazo dye. - Google Patents

Process for the preparation of a new monoazo dye.

Info

Publication number
CH257285A
CH257285A CH257285DA CH257285A CH 257285 A CH257285 A CH 257285A CH 257285D A CH257285D A CH 257285DA CH 257285 A CH257285 A CH 257285A
Authority
CH
Switzerland
Prior art keywords
sulfuric acid
dye
new
preparation
solution
Prior art date
Application number
Other languages
German (de)
Inventor
Limited Imperial Ch Industries
Original Assignee
Ici Ltd
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 Ici Ltd filed Critical Ici Ltd
Publication of CH257285A publication Critical patent/CH257285A/en

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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
    • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
    • C09B62/62—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an ethylenamino or N-acylated ethylenamino group or a —CO—NH—CH2—CH2—X group, wherein X is a halogen atom, a quaternary ammonium group or O-acyl and acyl is derived from an organic or inorganic acid, or a beta-substituted ethylamine group
    • C09B62/66—Azo dyes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)

Description

  

  Verfahren zur Herstellung     eines    neuen     Monoazofarbstoffes.       Die vorliegende Erfindung betrifft ein  Verfahren zur Herstellung eines neuen     hlono-          azofarbstoffes,    gemäss welchem     N-n-Hexyl-          N    - n -     j,-hy        droxy        propylanilin,        diazotiertes        4-          Nitro-2-cyananilin    und ein     Sulfatierungsmit-          tel    zusammen umgesetzt werden, derart,

   dass  die     Oxy        gruppe    in die entsprechende     Schwe-          felsäuree;stergruppe    übergeführt wird und  der     Diazorest    in     4-Stellung    zum tertiären       Stickstoffatom    tritt.  



  Der     neue:    Farbstoff ist ein dunkelgrünes  Pulver, welches in     Wasser    unter Bildung  einer     rötlichvioletten        Lösung    und in     konz.     Schwefelsäure unter Bildung einer     schoko-          ).adebraunen    Lösung löslich ist.  



       Dic        Oxygruppe    kann vor oder nach der       Kupplung    der     Diazokomponente    mit der       Kupplungskomponente    in die entsprechende       Schwefelsäureestergruppe    übergeführt wer  den.  



  <I>Beispiel:</I>  16,3 Teile     4-Nitro-2-cyananilin    werden  innerhalb 1 bis 2 Stunden in eine Lösung von       Nitrosylschwefelsäure,    erhalten durch Zugabe  von 6,9 Teilen     Natriumnitrit    zu 140 Teilen       honz.    Schwefelsäure, eingetragen und das  Gemisch während weiterer 1 bis 2 Stunden  gerührt. Die schwefelsaure Lösung     -wird     dann in einem Gemisch von 400 Teilen Eis  und 100 Teilen Wasser eingerührt.

   Die fil  trierte     Diazolösung    wird allmählich unter  Kühlen und Rühren in eine Lösung von 33,7  Teilen des     Natriumsalzes    des     N-n-Hexyl-N-          n-y-oxypropylanilin-schwefelsäureesters,    ge  löst in 400 Teilen Wasser eingetragen. Das         Kupplungsmedium    wird während einiger  Stunden gerührt und hierauf die     gekühlte          Suspension    allmählich mit     10n-wässriger        Na-          triumhydroxydlösung    versetzt, bis sie auf  Lackmus gerade alkalisch reagiert.

   Nach kur  zem Rühren wird der Farbstoff     abfiltriert,          mit    etwas Wasser gewaschen und bei 30 bis  40  C getrocknet.  



  Der neue Farbstoff bildet ein dunkelgrü  nes Pulver,     welches    sich in heissem Wasser  unter Bildung einer     rötlichvioletten    Lösung  und in     konz.    Schwefelsäure unter Bildung  einer schokoladebraunen Lösung löst. Er  färbt     Zelluloseacetatkunstseide    und     Poly-          amidfasern        au.    einem neutralen, Glaubersalz  oder     Natriumchlorid    enthaltenden Färbebade  in violetten Farbtönen von guter Echtheit  gegen     Nassbehandlung    und Licht.



  Process for the preparation of a new monoazo dye. The present invention relates to a process for the preparation of a new hlono azo dye, according to which N-n-hexyl- N - n - j, -hydroxy propylaniline, diazotized 4-nitro-2-cyananiline and a sulfating agent are reacted together, such as

   that the oxy group is converted into the corresponding sulfuric acid ester group and the diazo radical is in the 4-position to the tertiary nitrogen atom.



  The new: dye is a dark green powder, which in water to form a reddish-purple solution and in conc. Sulfuric acid is soluble to form a chocolate).



       The oxy group can be converted into the corresponding sulfuric acid ester group before or after the coupling of the diazo component with the coupling component.



  <I> Example: </I> 16.3 parts of 4-nitro-2-cyananiline are dissolved within 1 to 2 hours in a solution of nitrosylsulfuric acid, obtained by adding 6.9 parts of sodium nitrite to 140 parts of honey. Sulfuric acid, entered and the mixture stirred for a further 1 to 2 hours. The sulfuric acid solution is then stirred into a mixture of 400 parts of ice and 100 parts of water.

   The filtered diazo solution is gradually introduced into a solution of 33.7 parts of the sodium salt of N-n-hexyl-N-n-y-oxypropylaniline-sulfuric acid ester, dissolved in 400 parts of water, with cooling and stirring. The coupling medium is stirred for a few hours and then 10N aqueous sodium hydroxide solution is gradually added to the cooled suspension until it just reacts alkaline to litmus.

   After stirring for a short time, the dye is filtered off, washed with a little water and dried at 30 to 40.degree.



  The new dye forms a dark green powder, which in hot water forms a reddish-purple solution and in conc. Sulfuric acid dissolves to form a chocolate-brown solution. He dyes cellulose acetate artificial silk and polyamide fibers. a neutral dye bath containing Glauber's salt or sodium chloride in violet shades of good fastness to wet treatment and light.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen Dlonoazofarbstoffes, dadurch gekennzeichnet, dass N-n-Hexyl-N-u-y-oxypr opylanilin, diazo- tiertes 4-Nitro-2-cyananilin und ein Sulfatie- rungsmittel derart miteinander umgesetzt %verden, PATENT CLAIM: Process for the production of a new dlonoazo dye, characterized in that N-n-hexyl-N-u-y-oxypropylaniline, diazoated 4-nitro-2-cyananiline and a sulfating agent are reacted with one another in such a way that dass die Oxygruppe in die entspre chende Schwefelsäureestergruppe überge führt wird und der Diazorest in 4-Stellung zum tertiären Stickstoffatom tritt. Der neue Farbstoff ist ein dunkelgrünes Pulver, welches sich in Wasser unter Bil dung einer rötlichvioletten Lösung und in konz. Schwefelsäure unter Bildung einer schokoladebraunen Lösung löst. that the oxy group is converted into the corresponding sulfuric acid ester group and the diazo radical occurs in the 4-position to the tertiary nitrogen atom. The new dye is a dark green powder that dissolves in water to form a reddish-purple solution and in conc. Sulfuric acid dissolves to form a chocolate-brown solution.
CH257285D 1945-06-29 1946-06-27 Process for the preparation of a new monoazo dye. CH257285A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB257285X 1945-06-29
CH251392T 1946-06-27

Publications (1)

Publication Number Publication Date
CH257285A true CH257285A (en) 1948-09-30

Family

ID=25729537

Family Applications (1)

Application Number Title Priority Date Filing Date
CH257285D CH257285A (en) 1945-06-29 1946-06-27 Process for the preparation of a new monoazo dye.

Country Status (1)

Country Link
CH (1) CH257285A (en)

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