CH313096A - 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
CH313096A
CH313096A CH313096DA CH313096A CH 313096 A CH313096 A CH 313096A CH 313096D A CH313096D A CH 313096DA CH 313096 A CH313096 A CH 313096A
Authority
CH
Switzerland
Prior art keywords
water
dye
monoazo dye
insoluble monoazo
insoluble
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 CH313096A publication Critical patent/CH313096A/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)
  • Paints Or Removers (AREA)
  • Coloring (AREA)

Description

  

  <B>Verfahren</B>     zur   <B>Herstellung</B>     eines        wasserunlöslichen        Monoazofarbstoffes       Gegenstand des vorliegenden Patentes ist  ein Verfahren zur Herstellung eines wasserun  löslichen     Monoazofarbstoffes,    welches darin  besteht, dass man 1     Mol        diazotiertes        2-Amino-          5-nitrobenzol-l-sulfonsäurefluorid    in saurem  Medium mit 1     llol        1-(N-Äthy1        N-dioxäthyl-          amino)-3-aeetylamino-6-methoxybenzol    kup  pelt.  



  Der neue, wasserunlösliche     Monoazofarb-          stoff    stellt ein grünes Pulver dar, welches aus  Äthanol umkristallisiert bei 204  schmilzt. In  üblicher Weise     dispergiert,    färbt der Farb  stoff     Acetatreyon    in blauen Tönen, welche  rein weiss     ätzbar    sind.

   Seine Färbungen auf       sy        nthetisehen        Polyamidfasern    sind etwas     gelb-          stiehiger.    Der neue, wasserunlösliche     Monoazo-          farbstoff    eignet sich auch zum Färben von  Lacken, Ölen, Kunstharzen oder von künst  lichen Fasern in der Masse.  



  Im nachfolgenden Beispiel bedeuten die  Teile Gewichtsteile, und die Prozente sind in       CTewiehtsprozenten    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  gekühlt, bei dieser Tempe  ratur mit 100 Teilen konzentrierter Essig  säure und     hernach    mit 22 Teilen     2-Amino-          5-nitrobenzol-l-sulfonsäurefhiorid    versetzt,  worauf man erneut 100 Teile konzentrierte  Essigsäure zufügt.

   Nach einer Stunde stumpft    man den     Nitritüberschuss    der     Diazotierungs-          masse    mit 5 Teilen     Harnstoff    ab und bringt  sie anschliessend auf 250 Teile Eis. Hierauf  vereinigt man die     Diazotierinmgsmasse    mit  einer vorbereiteten Lösung von 27 Teilen 1-     (N-          Äthyl        -jN"    -     dioxäthylamino)    - 3 -     acetyla-mino        -i6        -          methoxybenzol,    100 Teilen Wasser, 20 Teilen  30 Niger     Salzsäure    und 100 Teilen Eis.

   Der  neue     Monoazofarbstoff        beginnt    alsbald auszu  fallen. Sobald dessen     Abscheidung    beendet ist,  wird er durch     Abfiltrieren    isoliert, mit  Wasser säurefrei gewaschen und hernach ge  trocknet.  



  Der neue, wasserunlösliche     Monoazofarb-          stoff    stellt ein grünes Pulver dar, welches  aus Äthanol umkristallisiert bei 204  schmilzt.  In üblicher Weise     dispergiert,    färbt der Farb  stoff     Acetatreyon    in blauen Tönen, welche  rein weiss     ätzbar    sind. Seine Färbungen auf       synthetischen        Polyamidfasern    sind etwas     gelb-          stichiger.    Der neue, wasserunlösliche     Mono-          azofarbstoff    eignet sich auch zum Färben von  Lacken, Ölen, Kunstharzen oder von künst  lichen Fasern in der Masse.



  <B> Process </B> for <B> Production </B> of a Water-Insoluble Monoazo Dye The present patent relates to a process for the production of a water-insoluble monoazo dye, which consists in adding 1 mol of diazotized 2-amino-5-nitrobenzene -l-sulfonic acid fluoride in an acid medium with 1 llol 1- (N-Ethy1 N-dioxäthyl- amino) -3-aetylamino-6-methoxybenzene kup pelt.



  The new, water-insoluble monoazo dye is a green powder which, recrystallized from ethanol, melts at 204. Dispersed in the usual way, the dye Acetatreyon colors in blue tones, which can be etched in pure white.

   Its colorations on synthetic polyamide fibers are somewhat more yellowish. The new, water-insoluble monoazo dye is also suitable for coloring paints, oils, synthetic resins or artificial fibers in the mass.



  In the following example, the parts are parts by weight and the percentages are given in percent 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 100 parts of concentrated acetic acid and then 22 parts of 2-amino-5-nitrobenzene-1-sulfonic acid chloride are added, whereupon 100 parts of concentrated acetic acid are again added.

   After one hour, the excess nitrite of the diazotization mass is blunted with 5 parts of urea and then placed on 250 parts of ice. The Diazotierinmgsmasse is then combined with a prepared solution of 27 parts of 1- (N-ethyl -jN "- dioxäthylamino) -3-acetyla-mino -i6-methoxybenzene, 100 parts of water, 20 parts of 30 Niger hydrochloric acid and 100 parts of ice.

   The new monoazo dye soon begins to fall out. 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 green powder which, recrystallized from ethanol, melts at 204. Dispersed in the usual way, the dye Acetatreyon colors in blue tones, which can be etched in pure white. Its coloring on synthetic polyamide fibers is a little more yellowish. The new, water-insoluble monoazo dye is also suitable for dyeing paints, oils, synthetic resins or artificial fibers in the mass.

Claims (1)

PATENTANSPRUCH Verfahren zur Herstellung eines wasser unlöslichen --,#lonoazofarbstoffes, dadurch ge kennzeichnet, dass man 1 Mol diazotiertes 2 Amino-5-nitrobenzol-l-sulfonsäurefluorid in saurem Medium mit 1 Mol 1-(N-Äthyl-N-di- oxäthylamino) - 3-acetylamino-6-methoxybenzol kuppelt. Der neue, wasserunlösliche Monoazofarb- stoff stellt ein grünes Pulver dar, welches aus Äthanol umkristallisiert bei 204 schmilzt. PATENT CLAIM Process for the preparation of a water-insoluble -, # lonoazo dye, characterized in that 1 mol of diazotized 2-amino-5-nitrobenzene-1-sulfonic acid fluoride in an acidic medium with 1 mol of 1- (N-ethyl-N-di-oxäthylamino ) - 3-acetylamino-6-methoxybenzene couples. The new, water-insoluble monoazo dye is a green powder which, recrystallized from ethanol, melts at 204. In üblicher Weise dispergiert, färbt der Farb stoff Aeetatreyon in blauen Tönen, welche rein weiss ätzbar sind. Seine Färbungen auf synthetischen Polyau iidfasern sind etwas gelb- st.ichiger. Der neue, wasserunlösliche Monoazo- farbstoff eignet sich auch zum Färben von Lacken, ölen, Kunstharzen oder von künst lichen Fasern in der Masse. Dispersed in the usual way, the dye Aeetatreyon colors in blue tones, which can be etched in pure white. Its coloring on synthetic polyamide fibers is a little more yellowish. The new, water-insoluble monoazo dye is also suitable for dyeing paints, oils, synthetic resins or artificial fibers in bulk.
CH313096D 1952-12-24 1952-12-24 Process for the preparation of a water-insoluble monoazo dye CH313096A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH313096T 1952-12-24
CH312188T 1952-12-24

Publications (1)

Publication Number Publication Date
CH313096A true CH313096A (en) 1956-03-15

Family

ID=25735875

Family Applications (1)

Application Number Title Priority Date Filing Date
CH313096D CH313096A (en) 1952-12-24 1952-12-24 Process for the preparation of a water-insoluble monoazo dye

Country Status (1)

Country Link
CH (1) CH313096A (en)

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