CH313101A - 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
CH313101A
CH313101A CH313101DA CH313101A CH 313101 A CH313101 A CH 313101A CH 313101D A CH313101D A CH 313101DA CH 313101 A CH313101 A CH 313101A
Authority
CH
Switzerland
Prior art keywords
water
monoazo dye
dye
insoluble monoazo
parts
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 CH313101A publication Critical patent/CH313101A/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)
  • Compositions Of Macromolecular Compounds (AREA)
  • Coloring (AREA)

Description

  

  <B>Verfahren</B>     zur   <B>Herstellung</B>     eines        wasserunlöslichen        Monoazofarbstoffes            tlegenstand    des vorliegenden Patentes ist  ein Verfahren zur Herstellung eines wasser  unlöslichen     llonoazofarbstoffes,    welches darin  besteht, dass man 1     Mol        diazotiertes    '2-     Amino-          5-nitrobenzol-l-stilfonsäurefluorid    in saurem  Medium mit 1     Mol        1-[N,N-:Bis(acetoxyäthyl)-          amino]-3-methylbenzol    kuppelt.  



  Der neue,     wasserunlösliehe        3Ionoazofarb-          atoff    stellt ein violettes Pulver dar, welches       a        us        Äthanol   <B>,</B>     umkristallisiert,        bei        190        bis        1930     schmilzt. In üblicher Weise     dispergiert,    färbt  der Farbstoff Polyesterfasern in rotvioletten  Tönen, welche sehr gute Echtheitseigenschaf  ten aufweisen. Er eignet sich auch zum Fär  ben von Lacken, Ölen, Kunstharzen oder von  künstlichen Fasern in der     Masse.     



  Im nachfolgenden Beispiel bedeuten die  Teile     Cewicht.steile,    und die Prozente sind in       Cewichtsprozenten    angegeben.         Beispiel.     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  säure und hernach mit 22 Teilen     2-Amino-          5    -     nitrobenzol    -1-     sulfonsäurefluorid    versetzt,

    worauf man     erneut    100 'Teile konzentrierte       Essigsäure        zufügt.    Nach     einer!Stunde    stumpft  man den     Nitritübersehuss    der     Diazotierungs-          masse    mit 5 Teilen     Harnstoff    ab und     bringt     sie anschliessend auf 250 Teile Eis.

   Hierauf  vereinigt man die     Diazotierungsmasse    mit  einer vorbereiteten Lösung von 38 Teilen 1-         [N,N        -Bis        (acetoxyäthyl)        --amino    ]     -3-methylben-          zol,        40    'Teilen Wasser, 20 Teilen     30prozen-          tiger    Salzsäure und     2.0    'Teilen Eis. Der neue       Monoazofarbstoff    beginnt alsbald auszufallen.

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



  Der neue,     wasserunlösliche        Monoazofarb-          stoff    stellt ein violettes Pulver dar, welches  aus Äthanol     umkristallisiert,    bei 190 bis 193   schmilzt. In üblicher Weise     dispergiert,    färbt  der Farbstoff Polyesterfasern in rotvioletten  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 </B> for the <B> production </B> of a water-insoluble monoazo dye The status of the present patent is a process for the production of a water-insoluble ionoazo dye, which consists in adding 1 mol of diazotized '2- amino- nitrobenzene-l-stilfonic acid fluoride in acidic medium with 1 mol of 1- [N, N-: bis (acetoxyethyl) amino] -3-methylbenzene couples.



  The new, water-insoluble 3ionoazo dye is a violet powder which recrystallizes from ethanol <B> </B> and melts between 190 and 1930. Dispersed in the usual way, the dye dyes polyester fibers in red-violet shades, which have very good fastness properties. It is also suitable for coloring paints, oils, synthetic resins or artificial fibers in the mass.



  In the following example, the parts mean Cewicht.steile, and the percentages are given in Cewicht%. Example. 7.6 parts of sodium nitrite are introduced at 60 in 90 parts of concentrated sulfuric acid within one hour.

   The solution obtained is cooled to 10, at this temperature with 100 parts of concentrated acetic acid and then with 22 parts of 2-amino-5-nitrobenzene-1-sulfonic acid fluoride,

    whereupon 100 parts of concentrated acetic acid are again added. After an hour, the excess nitrite in the diazotization compound is blunted with 5 parts of urea and then placed on 250 parts of ice.

   The diazotization mass is then combined with a prepared solution of 38 parts of 1- [N, N-bis (acetoxyethyl) amino] -3-methylbenzene, 40 parts of water, 20 parts of 30 percent hydrochloric acid and 2.0 parts of ice . The new monoazo dye soon begins to precipitate.

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



  The new, water-insoluble monoazo dye is a purple powder which recrystallises from ethanol and melts at 190 to 193. Dispersed in the usual way, the dye dyes polyester fibers in red-violet 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)

PATENTANSPRUCH Verfahren zur- Herstellung eines wasser unlöslichen Monoazofarbstoffes, dadurch ge kennzeichnet, dass man 1 Mol diazotiertes 2-Amino-5-nitrobenzol-l-sulfonsäurefluorid in saurem Medium mit 1 Mol 1-[N,N-Bis(acet- oxyäthyl)-amino]-3-methylbenzol kuppelt. Der nette, wasserunlösliche Monoazofarb- stoff stellt ein violettes Pulver dar, welches aus Äthanol umkristallisiert, bei 1:90 bis 19:3 schmilzt. PATENT CLAIM Process for the production of a water-insoluble monoazo dye, characterized in that 1 mol of diazotized 2-amino-5-nitrobenzene-l-sulfonic acid fluoride in an acidic medium with 1 mol of 1- [N, N-bis (acetoxyethyl) - amino] -3-methylbenzene couples. The nice, water-insoluble monoazo dye is a purple powder which recrystallises from ethanol and melts at 1:90 to 19: 3. In üblicher Weise dispergiert, färbt der Farbstoff Polyesterfasern in rotvioletten Tönen, welche sehr gute Echtheitseigenschaf ten aufweisen. Er eignet sich auch zum Fär ben von Lacken, Ölen, Kunstharzen oder von künstlichen Fasern in der Masse. Dispersed in the usual way, the dye dyes polyester fibers in red-violet shades, which have very good fastness properties. It is also suitable for coloring paints, oils, synthetic resins or artificial fibers in the mass.
CH313101D 1952-12-24 1952-12-24 Process for the preparation of a water-insoluble monoazo dye CH313101A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH312188T 1952-12-24
CH313101T 1952-12-24

Publications (1)

Publication Number Publication Date
CH313101A true CH313101A (en) 1956-03-15

Family

ID=25735880

Family Applications (1)

Application Number Title Priority Date Filing Date
CH313101D CH313101A (en) 1952-12-24 1952-12-24 Process for the preparation of a water-insoluble monoazo dye

Country Status (1)

Country Link
CH (1) CH313101A (en)

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