CH313102A - Process for the preparation of a water-insoluble monoazo dye - Google Patents

Process for the preparation of a water-insoluble monoazo dye

Info

Publication number
CH313102A
CH313102A CH313102DA CH313102A CH 313102 A CH313102 A CH 313102A CH 313102D A CH313102D A CH 313102DA CH 313102 A CH313102 A CH 313102A
Authority
CH
Switzerland
Prior art keywords
water
monoazo dye
preparation
parts
amino
Prior art date
Application number
Other languages
German (de)
Inventor
Ernst Dr Merian
Original Assignee
Sandoz 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 Sandoz Ag filed Critical Sandoz Ag
Publication of CH313102A publication Critical patent/CH313102A/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
    • 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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
    • C09B29/08—Amino benzenes
    • 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
    • C09B62/78—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 with other reactive groups

Landscapes

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

Description

  

  <B>Verfahren zur Herstellung eines wasserunlöslichen</B>     Monoazofarbstoffes            Gegenstand    des vorliegenden Patentes ist  ein Verfahren zur Herstellung eines wasser  unlöslichen     Monoazofarbstoffes,    welches     darin          besteht,        da.ss    man 1     Mol        diazotiertes        2-Amino-          5-nitrobenzol    -1-     sulfonsäurefluorid    in saurem  Medium mit. 1     Mol        1-[N,N=Bis(acetoxyäthyl)-          amino]-3-chlorbenzol    kuppelt.  



  Der neue, wasserunlösliche     Monoazofarb-          stoff    stellt ein rotviolettes Pulver dar, wel  ches aus Äthanol umkristallisiert, bei 152 bis       1,54     schmilzt. In üblicher Weise     dispergiert,     färbt der Farbstoff Polyesterfasern in wein  roten Tönen, welche sehr gute Echtheits  eigenschaften aufweisen. Er eignet. sich auch  zum Färben von Lacken, Ölen, Kunstharzen  oder von künstlichen     Fasern    in der Masse.  



  Im nachfolgenden Beispiel bedeuten die  Teile Gewichtsteile und die Prozente sind in  Gewichtsprozenten angegeben.    <I>Beispiel</I>  7,6 Teile     Natriumnitrit    werden innerhalb  einer Stunde bei 60  in 90 Teile konzentrierte  Schwefelsäure eingetragen. Die erhaltene Lö  sung wird auf 10  abgekühlt, bei dieser Tem  peratur mit 100 Teilen konzentrierter Essig  <B>s.</B>     itire    und hernach mit. 22 Teilen     2=Amino-5-          tiit.i-obenzol-l-sulfonsäurefluorid    versetzt, wor  auf man erneut.     100    Teile     konzentrierte    Essig  säure zufügt.

   Nach einer     Stunde    stumpft man       i    den     Nitritüberschuss    der     Diazotierungsmasse     mit 5 'Teilen Harnstoff ab und     bringt.    sie  anschliessend auf<B>250,</B> Teile Eis. Hierauf ver  einigt man die     Diazotierungsmasse    mit einer  vorbereiteten Lösung von 30 'Teilen 1-[N,N-         Bis(acetoxyäthyl)-        amino]    - 3 -     chlorbenzol,    40  Teilen Wasser, 20 Teilen 30prozentiger .Salz  säure und 20 Teilen Eis. Der neue     Monoazo-          fa.rbstoff    beginnt alsbald auszufallen.

   Sobald  dessen     Abscheidumg    beendet ist,     wird    er durch       Abfiltrieren    isoliert,     mit        Wasser    säurefrei  gewaschen     und    hernach getrocknet.  



  Der neue,     wasserunlösliche        Monoazofarb-          stoff    stellt     ein    rotviolettes Pulver dar, wel  ches aus Äthanol     urankristallisiert,    bei 152- bis       15,4     schmilzt. In üblicher Weise     dispergiert,     färbt der Farbstoff     Polvesterfasern    in wein  roten Tönen, welche sehr     gute    Echtheitseigen  schaften aufweisen. Er eignet sich auch zum  Färben von Lacken, Ölen,     Kunstharzen    oder  von künstlichen Fasern in der Masse.



  <B> Process for the preparation of a water-insoluble </B> monoazo dye The present patent relates to a process for the preparation of a water-insoluble monoazo dye, which consists in that 1 mol of diazotized 2-amino-5-nitrobenzene-1-sulfonic acid fluoride is added acid medium with. 1 mol of 1- [N, N = bis (acetoxyethyl) amino] -3-chlorobenzene couples.



  The new, water-insoluble monoazo dye is a red-violet powder which, recrystallized from ethanol, melts at 152 to 1.54. Dispersed in the usual way, the dye dyes polyester fibers in wine-red shades, which have very good fastness properties. He is suitable. can also be used to color paints, oils, synthetic resins or artificial fibers in bulk.



  In the following example, the parts are parts by weight and the percentages are given in percentages by weight. <I> Example </I> 7.6 parts of sodium nitrite are introduced within one hour at 60 to 90 parts of concentrated sulfuric acid. The solution obtained is cooled to 10, at this temperature with 100 parts of concentrated vinegar <B> s. </B> itire and then with. 22 parts of 2 = Amino-5-tiit.i -obenzol-l-sulfonic acid fluoride are added, which is repeated. 100 parts of concentrated acetic acid are added.

   After one hour, the excess nitrite of the diazotization compound is blunted with 5 parts of urea and brought. put them on <B> 250 </B> parts of ice. The diazotization mass is then combined with a prepared solution of 30 parts of 1- [N, N-bis (acetoxyethyl) amino] -3-chlorobenzene, 40 parts of water, 20 parts of 30 percent hydrochloric acid and 20 parts of ice. The new monoazo dye soon begins to precipitate.

   As soon as its deposition has ended, it is isolated by filtering off, washed acid-free with water and then dried.



  The new, water-insoluble monoazo dye is a red-violet powder that crystallizes uranium from ethanol and melts at 152 to 15.4. Dispersed in the usual way, the dye dyes Polvester fibers in wine-red shades, which have very good fastness properties. It is also suitable for coloring paints, oils, synthetic resins or artificial fibers in the mass.

Claims (1)

<B>PATENTANSPRUCH</B> Verfahren zur Herstellung eines wasser unlöslichen Monoazofarbstoffes, dadurch ge kennzeichnet, dass man 1 Mol diazotiertes 2- Amino-'5-nitrobenzol -1- sulfonsäurefluorid in saurem Medium mit 1 Mol 1-[N,N-Bis(acet- oxyäthyl) -amino ] -3-ehlorbenzol kuppelt: <B> PATENT CLAIM </B> Process for the preparation of a water-insoluble monoazo dye, characterized in that 1 mol of diazotized 2-amino-'5-nitrobenzene -1-sulfonic acid fluoride is mixed with 1 mol of 1- [N, N- Bis (acetoxyethyl) amino] -3-chlorobenzene couples: ,Der neue, wassermilösliche Monoazofarb- stoff stellt ein rotviolettes Pulver dar, wel ches aus Äthanol umkristallisiert, bei 152 bis 1540 schmilzt. In üblicher Weise dispergiert, färbt der Farbstoff Polyesterfasern in wein roten Tönen, welche sehr gute Echtheitseigen schaften aufweisen. Er eignet sich auch zum Färben von Lacken, Ölen, Kunstharzen oder von künstlichen Fasern in der Masse. The new, water-soluble monoazo dye is a red-violet powder which recrystallises from ethanol and melts at 152-1540. Dispersed in the usual way, the dye dyes polyester fibers in wine-red shades, which have very good fastness properties. It is also suitable for coloring lacquers, oils, synthetic resins or artificial fibers in the mass.
CH313102D 1952-12-24 1952-12-24 Process for the preparation of a water-insoluble monoazo dye CH313102A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH312188T 1952-12-24
CH313102T 1952-12-24

Publications (1)

Publication Number Publication Date
CH313102A true CH313102A (en) 1956-03-15

Family

ID=25735881

Family Applications (1)

Application Number Title Priority Date Filing Date
CH313102D CH313102A (en) 1952-12-24 1952-12-24 Process for the preparation of a water-insoluble monoazo dye

Country Status (1)

Country Link
CH (1) CH313102A (en)

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