CH261269A - Process for the preparation of a new monoazo dye. - Google Patents

Process for the preparation of a new monoazo dye.

Info

Publication number
CH261269A
CH261269A CH261269DA CH261269A CH 261269 A CH261269 A CH 261269A CH 261269D A CH261269D A CH 261269DA CH 261269 A CH261269 A CH 261269A
Authority
CH
Switzerland
Prior art keywords
oxyethyl
sulfuric acid
chloro
phenylethylaniline
preparation
Prior art date
Application number
Other languages
German (de)
Inventor
Limited Imperial Ch Industries
Original Assignee
Ici Ltd
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 Ici Ltd filed Critical Ici Ltd
Publication of CH261269A publication Critical patent/CH261269A/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
    • 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
    • C09B62/62—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 the reactive group being an ethylenimino or N—acylated ethylenimino group or a —CO—NH—CH2—CH2—X group, wherein X is a halogen atom, a quaternary ammonium group or O—acyl and acyl is derived from an organic or inorganic acid, or a beta—substituted ethylamine group
    • C09B62/66—Azo dyes

Landscapes

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

Description

  

  Verfahren zur Herstellung eines neuen     Monoazofarbstoffes.       Die Erfindung betrifft ein Verfahren zur  Herstellung eines neuen     Monoazofarbstoffes,     welcher dadurch erhalten wird, dass man     N-fl-          Oxyäthyl-N-ss'-phenyläthylanilin,    dianotiertes       o-Chlor-p-nitranilin    und ein     Sulfurieritngs-          mittel    miteinander dermassen zur Umsetzung  bringt,

   dass die     Oxyäthylgruppe    in die ent  sprechende     Schwefelsäureestergruppe    überge  führt wird und der     Diazorest    in die     4-Stel-          lung    zum tertiären Stickstoffatom eintritt.  Um den neuen Farbstoff zu erhalten, kann  man     N-fl-Oxyäthyl-N-ss"-phenyläthylanilin    ent  weder zuerst mit dianotiertem     o-Chlor-p-ni-          tranilin    kuppeln und hierauf das Kupplungs  produkt in den entsprechenden Schwefel  säureester überführen oder zuerst     sulfieren     und das erzielte Produkt mit dianotiertem       o-Chlor-nitranilin    kuppeln.  



  Der neue Farbstoff bildet ein dunkelgrün  liches Pulver, welches in Wasser unter Bil  dung einer roten Lösung und in Schwefel  säure unter Bildung einer braunen Lösung  löslich ist.  



  <I>Beispiel:</I>  Eine feine Suspension von 17,3 Teilen       o-Chlor-p-nitranilin    in 300 Teilen Wasser und  30 Teilen     36%iger    Salzsäure wird durch Zu  gabe von 6,9 Teilen     Natriumnitrit,    gelöst in  50 Teilen Wasser, dianotiert. Die     auf    50 C ge  kühlte, filtrierte Lösung der     Diazoverbindung     wird langsam einer ähnlich gekühlten Lösung  von 34,3 Teilen des     Natriumsalzes    des     Schwe-          felsäureesters    des N-fl'-Oxyäthyl-N-fl'-phenyl-         äthylanilins    in 400 Teilen Wasser unter Rüh  ren zugesetzt.

   Nachdem das Gemisch während  einer Stunde gerührt wurde, wird genügend       wässriges,    50%iges     Natriumaeetat    hinzuge  fügt, um das mineralsaure Kupplungsmedium  abzustumpfen. Die Suspension des     Monoazo-          farbstoffes    wird nun durch Zugabe von     5n-          Natronlauge    auf     Brilliantgelb    schwach alka  lisch gestellt. Der Farbstoff wird hierauf ab  filtriert, mit 21/2 %     iger,    wässriger Natrium  chloridlösung gewaschen und bei 30 bis 400 C  getrocknet.  



  Der neue Farbstoff bildet ein dunkelgrün  liches Pulver, das sich in Wasser mit roter  Färbung und in     konz.    Schwefelsäure mit  brauner Farbe löst. Er färbt     Zelluloseacetat-          kunstseide    und Nylon in karminroten Farb  tönen, sofern die Ausfärbung aus einem neu  tralen Färbebade, welches Glaubersalz oder       Natriumchlorid    enthält, vorgenommen wird,  wobei die erzeugten Färbungen gute Echt  heitseigenschaften gegen     Nassbehandlung    und  Licht sowie gute     Ätzbarkeit    aufweisen und       sublimierecht    sind.  



  Der in diesem Beispiel verwendete     Schwe-          felsäureester    wird durch Umsetzung der ent  sprechenden,     Oxyverbindung    mit     Chlorsulfon-          säure    in     Tetrachloräthan    erhalten.



  Process for the preparation of a new monoazo dye. The invention relates to a process for the preparation of a new monoazo dye which is obtained by reacting N-fl-oxyethyl-N-ss'-phenylethylaniline, dianotated o-chloro-p-nitroaniline and a sulfurizing agent with one another in such a way that

   that the oxyethyl group is converted into the corresponding sulfuric acid ester group and the diazo radical enters the 4-position to the tertiary nitrogen atom. To obtain the new dye, N-fl-Oxyäthyl-N-ss "-phenyläthylanilin ent either first couple with dianotated o-chloro-p-nitraniline and then convert the coupling product into the corresponding sulfuric acid ester or sulfate first and couple the product obtained with dianotized o-chloro-nitroaniline.



  The new dye forms a dark green powder which is soluble in water to form a red solution and in sulfuric acid to form a brown solution.



  <I> Example: </I> A fine suspension of 17.3 parts of o-chloro-p-nitroaniline in 300 parts of water and 30 parts of 36% strength hydrochloric acid is obtained by adding 6.9 parts of sodium nitrite, dissolved in 50 parts Water, dianotized. The filtered solution of the diazo compound cooled to 50 ° C. is slowly added to a similarly cooled solution of 34.3 parts of the sodium salt of the sulfuric acid ester of N-fl'-oxyethyl-N-fl'-phenylethylaniline in 400 parts of water with stirring Ren added.

   After the mixture has been stirred for one hour, sufficient aqueous 50% sodium acetate is added to blunt the mineral acid coupling medium. The suspension of the monoazo dye is now made weakly alkaline to brilliant yellow by adding 5N sodium hydroxide solution. The dye is then filtered off, washed with 21/2% strength aqueous sodium chloride solution and dried at 30.degree. To 400.degree.



  The new dye forms a dark green Lich powder, which turns red in water and in conc. Sulfuric acid dissolves with a brown color. It dyes cellulose acetate rayon and nylon in carmine-red shades, provided that the dyeing is carried out from a neutral dye bath containing Glauber's salt or sodium chloride, whereby the dyeings produced have good fastness properties against wet treatment and light as well as good etchability and are sublime-resistant.



  The sulfuric acid ester used in this example is obtained by reacting the corresponding oxy compound with chlorosulfonic acid in tetrachloroethane.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen Monoazofarbstoffes, dadurch gekennzeichnet, dass man N-fl'-Oxyäthyl-N-ss''-phenyläthylani- lin, diazotiertes o-Chlor-p-nitranilin und ein Sulfurierimgsmittel miteinander dermassen zur Umsetzung bringt, PATENT CLAIM: Process for the preparation of a new monoazo dye, characterized in that N-fl'-oxyethyl-N-ss "- phenylethylaniline, diazotized o-chloro-p-nitroaniline and a sulfurizing agent are reacted with one another in such a way that dass die Oxyäthyl- gruppe in die entsprechende Schwefelsäure estergruppe übergeführt wird und der Diazo- restin die 4-Stellung zum tertiären Stickstoff atom eintritt. that the oxyethyl group is converted into the corresponding sulfuric acid ester group and the diazo residue enters the 4-position to the tertiary nitrogen atom. Der neue Farbstoff bildet ein dunkelgrün- liches Pulver, welches in Wasser unter Bil dung einer roten Lösung und in Schwefel säure unter Bildung einer braunen Lösung löslich ist. The new dye forms a dark greenish powder, which is soluble in water to form a red solution and in sulfuric acid to form a brown solution. UNTERANSPRüCHE 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass N-ss-Oxyäthyl-N- ss'-phenyläthylanilin mit diazotiertem o-Chlor- p-nitranilin gekuppelt und das Kupplungs produkt zum entsprechenden Schwefelsäure ester sulfiert wird. 2. SUBClaims 1. The method according to claim, characterized in that N-ss-oxyethyl-N-ss'-phenylethylaniline is coupled with diazotized o-chloro-p-nitroaniline and the coupling product is sulfated to the corresponding sulfuric acid ester. 2. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass N-ss-Oxyäthyl-N- ss'-phenyläthylanilin sulfiert und das erzielte Produkt mit diazotiertem. o-Chlor-p-nitranüin gekuppelt wird. Process according to claim, characterized in that N-ss-oxyethyl-N-ss'-phenylethylaniline sulfates and the product obtained is diazotized. o-chloro-p-nitranuine is coupled.
CH261269D 1944-08-28 1945-08-28 Process for the preparation of a new monoazo dye. CH261269A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB261269X 1944-08-28
CH252136T 1947-12-15

Publications (1)

Publication Number Publication Date
CH261269A true CH261269A (en) 1949-04-30

Family

ID=25729592

Family Applications (1)

Application Number Title Priority Date Filing Date
CH261269D CH261269A (en) 1944-08-28 1945-08-28 Process for the preparation of a new monoazo dye.

Country Status (1)

Country Link
CH (1) CH261269A (en)

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