CH313094A - 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
CH313094A
CH313094A CH313094DA CH313094A CH 313094 A CH313094 A CH 313094A CH 313094D A CH313094D A CH 313094DA CH 313094 A CH313094 A CH 313094A
Authority
CH
Switzerland
Prior art keywords
water
monoazo dye
insoluble
insoluble monoazo
dye
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 CH313094A publication Critical patent/CH313094A/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

  

  Verfahren zur Herstellung eines wasserunlöslichen     Monoazofarbatoffes            Gegenstand    des vorliegenden Patentes ist  ein Verfahren zur Herstellung eines wasser  unlöslichen     Monoa.zofarbstoffes,    welches darin  besteht,     dass    man 1     Mol        diazotiertes        2-Amino-          5-nitrobenzol-l-sulfonsäurefluorid    in saurem  Medium mit 1     Mol        1-(N-Äthyl-N-dioxypropyl-          amino)-3-methylbenzol    kuppelt.  



  Der neue, wasserunlösliche     Monoazofarb-          stoff    stellt ein dunkelviolettes Pulver dar,  welches aus Äthanol umkristallisiert bei 189  bis 190  schmilzt. In üblicher Weise     disper-          giert,    färbt der Farbstoff     Acetatreyon    in vio  letten     Tönen,    welche hervorragend lichtecht  und rein weiss     ätzba.r    sind.

   Seine Färbungen  auf     synthetischen        Polyamidfasern    sind etwas       gelbstichiger.    Der neue, wasserunlösliche       Monoazofarbstoff    eignet sich auch zum Fär  ben von Lacken, Ölen, Kunstharzen oder von  künstlichen Fasern in der Masse.    Im nachfolgenden Beispiel bedeuten die  Teile Gewichtsteile, lind     die    Prozente sind in       Gewichtsprozenten        angegeben.       <I>Beispiel</I>  7,6 Teile     Natriumnitrit    werden innerhalb  einer .Stunde bei 60  in 90 Teile konzentrierte       Schwefelsä#ure    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     Nitritüberschuss    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 21 Teilen  1-     (N-Äthyl-N-,dioxypropylamino)-3-methyl-          benzol,    100 Teilen Wasser, 20 Teilen 30      /oiger     Salzsäure und 100 Teilen Eis. Der neue     Mono-          azofarbstoff    beginnt alsbald auszufallen. So  bald dessen     Abscheidung    beendet ist, wird er  durch     Abfiltrieren    isoliert, mit     Wasser    säure  frei gewaschen und hernach getrocknet.  



  Der neue,     wasserunlösliche        Monoazofarb-          stoff    stellt ein     diuikelviolettes    Pulver dar,       welches    aus Äthanol     umkristallisiert    bei 189  bis 190  schmilzt. In üblicher Weise     disper-          giert,    färbt der Farbstoff     Acetatreyon    in vio  letten Tönen, welche hervorragend lichtecht       und    rein weiss     ätzbar    sind.

   Seine Färbungen  auf     synthetischen        Polyamidfasern    sind etwas       gelbstichiger.    Der neue,     wasserunlösliche          Monoazofarbstoff    eignet sich auch zum Fär  ben von Lacken, Ölen, Kunstharzen oder von       künstlichen    Fasern in der Masse.



  Process for the preparation of a water-insoluble monoazo dye The present patent relates to a process for the preparation of a water-insoluble monoazo dye, which consists in adding 1 mol of diazotized 2-amino-5-nitrobenzene-1-sulfonic acid fluoride in an acidic medium with 1 mol of 1- (N-ethyl-N-dioxypropyl-amino) -3-methylbenzene couples.



  The new, water-insoluble monoazo dye is a dark purple powder which, recrystallized from ethanol, melts at 189-190. When dispersed in the usual way, the dye Acetatreyon dyes in violet tones, which are extremely lightfast and 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. 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 in 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. 22 parts of 2-amino-5-nitrobenzene-1-sulfonic acid fluoride are then added, whereupon 100 parts of concentrated acetic acid are again added. After one hour, the following are blunted: the excess nitrite of the diazotization mass with 5 parts of urea and then brought to 250 parts of ice.

   The diazotization mass is then combined with a prepared solution of 21 parts of 1- (N-ethyl-N-, dioxypropylamino) -3-methylbenzene, 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 has ended, it is isolated by filtering off, washed acid-free with water and then dried.



  The new, water-insoluble monoazo dye is a light-violet powder which, recrystallized from ethanol, melts at 189-190. When dispersed in the usual way, the dye Acetatreyon dyes in violet shades, which are extremely lightfast and 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.

Claims (1)

PATENTANSPRUCH Verfahren zur Herstellung eines wasser unlöslichen Monoa.zofa.rbstoffes, dadurch ge kennzeichnet, da.ss man 1 Mol diazotiertes 2-Amino-5-nitrobenzol-l-sulfonsäurefluorid in saurem Medium mit 1 Mal 1-(N-Äthyl-N-di- oxypropylamino)-3-methylbenzol kuppelt. PATENT CLAIM Process for the production of a water-insoluble Monoa.zofa.rstoffes, characterized in that 1 mol of diazotized 2-amino-5-nitrobenzene-l-sulfonic acid fluoride in an acidic medium with 1 time 1- (N-ethyl-N- di- oxypropylamino) -3-methylbenzene couples. Der neue, wasserunlösliche Monoazofarb- stoff stellt .ein dunkelviolettes Pulver dar, welches aus Äthanol umkristallisiert bei 189 bis 190 schmilzt. In üblicher Weise disper- giert, färbt der Farbstoff Acetatreyon in vio letten Tönen, welche hervorragend lichtecht. und rein weiss ätzbar sind. The new, water-insoluble monoazo dye is a dark purple powder which, recrystallized from ethanol, melts at 189 to 190. When dispersed in the usual way, the dye Acetatreyon dyes in violet shades, which are outstandingly lightfast. and can be etched in pure white. Seine Färbungen auf synthetischen Polyamidfasern sind etwas gelbstichiger. Der neue, wasserunlösliche Monoazofarbstoff eignet, sieh auch zum Fär ben von Lacken, ölen, Kunstharzen oder von künstlichen Fasern in der Masse. Its coloring on synthetic polyamide fibers is a little more yellowish. The new, water-insoluble monoazo dye is also suitable for dyeing varnishes, oils, synthetic resins or artificial fibers in bulk.
CH313094D 1952-12-24 1952-12-24 Process for the preparation of a water-insoluble monoazo dye CH313094A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH313094T 1952-12-24
CH312188T 1952-12-24

Publications (1)

Publication Number Publication Date
CH313094A true CH313094A (en) 1956-03-15

Family

ID=25735873

Family Applications (1)

Application Number Title Priority Date Filing Date
CH313094D CH313094A (en) 1952-12-24 1952-12-24 Process for the preparation of a water-insoluble monoazo dye

Country Status (1)

Country Link
CH (1) CH313094A (en)

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