CH313095A - 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
CH313095A
CH313095A CH313095DA CH313095A CH 313095 A CH313095 A CH 313095A CH 313095D A CH313095D A CH 313095DA CH 313095 A CH313095 A CH 313095A
Authority
CH
Switzerland
Prior art keywords
water
monoazo dye
insoluble
preparation
new
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 CH313095A publication Critical patent/CH313095A/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)

Description

  

  Verfahren     zur    Herstellung eines wasserunlöslichen     Monoazofarbstoffes            Gegenstand    des vorliegenden Patentes ist.  ein Verfahren zur     Herstellung    eines wasser  unlöslichen     Monoazofa.rbstoffes,    welches darin  besteht, dass man 1     Mol        diazotiertes        2-Amino-          5-nitrobenzol-l-sulfonsä#urefluorid    in saurem  Medium mit. 1     Mol        1-(N-Äthyl-N-dioxäthyl-          amino)-3-a,cetvlaminobenzol    kuppelt.  



  Der neue, wasserunlösliche     Monoazofarb-          stoff    stellt ein grünes Pulver dar, welches aus       Äthanol        umkristallisiert.    bei 190      schmilzt.    In  üblicher Weise     dispergiert,    färbt der Farb  stoff     Aeeta.treyon    in violetten Tönen, welche  lichtecht und rein weiss     ätzbar    sind.

   Seine       Färbungen    auf synthetischen     Polyamidfasern     sind etwas     gelbstichiger.    Der neue, wasser  unlösliche     Monoazofarbstoff    eignet sieh 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     Natriumniti@it    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    -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     Diazotierimgsmasse    mit  einer vorbereiteten Lösung von 24 Teilen  1-     (N-Äthy    1-     N-dioxäthylamino)        -'3-a.cetylamino-          benzol,    100 Teilen Wasser, 20 Teilen 30     o/oiger     Salzsäure     und    100 Teilen Eis.

   Der neue       Monoazofarbstoff        beginnt    alsbald     auszufallen.     Sobald dessen     Abscheidung        beendef    ist, wird  er durch     Abfiltrieren    isoliert, mit     Wasser     säurefrei gewaschen und hernach getrocknet.  



  Der neue,     wasserunlösliche        iMonoazofarb-          stoff    stehlt ein grünes Pulver dar, welches aus  Äthanol     umkristallisiert    bei 190  schmilzt. In  üblicher Weise     dispergiert,    färbt der Farb  stoff     Acetatreyon    in violetten Tönen, welche  lichtecht und rein weiss     ätzbar    sind.

   Seine  Färbungen auf synthetischen     Polyamidfasern     sind etwas     gelbstichiger.    Der neue, wasser  unlösliche     Monoazofarbstoff        eignet    sieh auch  zum Färben von Lacken, Ölen,     Kunstharzen     oder von künstlichen Fasern in der Masse.



  Process for the preparation of a water-insoluble monoazo dye is the subject of the present patent. a process for the preparation of a water-insoluble monoazofa dye, which consists in adding 1 mol of diazotized 2-amino-5-nitrobenzene-1-sulfonic acid fluoride in an acidic medium. 1 mol of 1- (N-ethyl-N-dioxäthylamino) -3-a, cetvlaminobenzene couples.



  The new, water-insoluble monoazo dye is a green powder that recrystallizes from ethanol. melts at 190. Dispersed in the usual way, the dye Aeeta.treyon colors in violet shades, which are lightfast and etchable in pure white.

   Its coloring on synthetic polyamide fibers is a little more yellowish. The new, water-insoluble monoazo dye is also suitable for coloring paints, oils, synthetic resins or artificial fibers in bulk.



  In the following example, parts are parts by weight and percentages are percentages by weight.



  <I> Example </I> 7.6 parts of sodium nitrate are introduced within one hour at 60 to 90 parts of concentrated sulfuric acid. The solution obtained is cooled to 10, at this Tempe 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 one hour, the excess nitrite in the diazotization compound is blunted with 5 parts of urea and then placed on 250 parts of ice. The Diazotierimgsmasse is then combined with a prepared solution of 24 parts of 1- (N-Ethy 1- N-dioxäthylamino) -'3-a.cetylaminobenzene, 100 parts of water, 20 parts of 30% hydrochloric acid and 100 parts of ice.

   The new monoazo dye soon begins to precipitate. As soon as its deposition is complete, it is isolated by filtration, washed acid-free with water and then dried.



  The new, water-insoluble iMonoazo dye is a green powder which, recrystallized from ethanol, melts at 190. Dispersed in the usual way, the dye Acetatreyon turns violet tones, which are lightfast and etchable in pure white.

   Its coloring on synthetic polyamide fibers is a little more yellowish. The new, water-insoluble monoazo dye is also suitable for coloring paints, oils, synthetic resins or artificial fibers in bulk.

Claims (1)

PATENTANSPRUCH Verfahren zur Herstellung eines wasser unlöslichen Monoazofarbstoffes, dadurch ge- kennzeichnet, dass man 1 Mol diagotiertes 2-Amino-5-nitrobenzol-l-sulfonsäurefluorid in saurem Medium mit 1 Mol 1- (N-Äthyl-N-di- oxäthylamino)-3-a.cetylaminobenzol kuppelt. PATENT CLAIM A process for the preparation of a water-insoluble monoazo dye, characterized in that 1 mol of diagotated 2-amino-5-nitrobenzene-1-sulfonic acid fluoride is mixed with 1 mol of 1- (N-ethyl-N-dioxäthylamino) 3-a.cetylaminobenzene couples. Der neue, wasserunlösliche Monoazofa,rb- stoff stellt ein grünes Pulver dar, welches aus Äthanol umkristallisiert bei 190 schmilzt. In iiblieher Weise dispergiert, färbt der Fa.rl)- stoff Aeetatreyon in violetten Tönen, welehe lichtecht und rein weiss ätzbar sind. The new, water-insoluble monoazofa, rb- stoff is a green powder which, recrystallized from ethanol, melts at 190. Dispersed in the usual way, the company dyes acetate grayon in violet tones, which are lightfast and can be etched in pure white. Seine Färbungen auf synthetisehen Polyamidfaser,n sind etwas gelbstiehiger. Der neue, wasser- unlösliehe Monoazofarbstoff eignet sieh aueh zum Färben von Lacken, Ölen, Kunstharzen oder von künstliehen Fasern in der :Masse. 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.
CH313095D 1952-12-24 1952-12-24 Process for the preparation of a water-insoluble monoazo dye CH313095A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH312188T 1952-12-24
CH313095T 1952-12-24

Publications (1)

Publication Number Publication Date
CH313095A true CH313095A (en) 1956-03-15

Family

ID=25735874

Family Applications (1)

Application Number Title Priority Date Filing Date
CH313095D CH313095A (en) 1952-12-24 1952-12-24 Process for the preparation of a water-insoluble monoazo dye

Country Status (1)

Country Link
CH (1) CH313095A (en)

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