CH261274A - Process for the preparation of a new monoazo dye. - Google Patents

Process for the preparation of a new monoazo dye.

Info

Publication number
CH261274A
CH261274A CH261274DA CH261274A CH 261274 A CH261274 A CH 261274A CH 261274D A CH261274D A CH 261274DA CH 261274 A CH261274 A CH 261274A
Authority
CH
Switzerland
Prior art keywords
oxyethyl
sulfuric acid
diazotized
dichloro
tolylethylaniline
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 CH261274A publication Critical patent/CH261274A/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 ethylenamino or N-acylated ethylenamino 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,     da.ss    man     N-ss-          Oxyäthy        1-N-ss'-p-tolyläthylanilin,        diazotiertes          2,6-Dichlor-4-nitranilin    und ein     Sulfurie-          rungsmittel    miteinander     dermassen        zur    Um  setzung bringt,

       da.ss    die     Oxyäthylgruppe    in  die entsprechende     Schwefelsäureestergruppe     übergeführt wird und der     Diazorest    in die       4-Stellung    zum tertiären Stickstoffatom ein  tritt.

   Um den neuen Farbstoff zu erhalten,  kann man     N-ss-Oxyäthyl-N-ss'-p-tolyläthylani-          lin    entweder zuerst mit     diazotiertem        2,6-Di-          chlor-4-nitranilin    kuppeln und hierauf das  Kupplungsprodukt in den entsprechenden       Schwefelsäureester    überführen oder zuerst       sulfieren    und das erzielte Produkt mit     diazo-          tiertem        2,6-Diehlor-4-nitranilin    kuppeln.  



  Der neue Farbstoff bildet ein schwarzes  Pulver, welches in Wasser unter Lösung     einer     hellorangen Lösung     und    in     Schwefelsäure    un  ter Bildung     einer    schokoladebraunen Lösung  löslich ist. Er     färbt        Zelluloseacetatkunstseide     in orangen Tönen.  



  <I>Beispiel:</I>  20,7 Teile     2,6-Dichlor-4-nitranilin    werden  durch allmähliche Zugabe einer     Lösung    von  6,9 Teilen trockenem     Natriumnitrit    in 148  Teilen     konz.    Schwefelsäure     diazotiert.    Die  schwefelsaure Lösung wird während ein bis  zwei Stunden gerührt und hierauf einem Ge  misch von 400 Teilen Eis und 100 Teilen  Wasser zugesetzt.

   Die filtrierte Lösung der         Diazoverbindung    wird     allmählich    einer eis  kalten Lösung von 35,7 Teilen des     Natriiun-          salzes    des     Schw        efelsäureesters    von     N-ss-Oxy-          äthy        1-N-ss'-p-tolyläthylanilin    in 400 Teilen  Wasser zugesetzt. Gleichzeitig mit der Zu  gabe der     Diazolösung    versetzt man mit  40%     iger,    wässriger Natronlauge dermassen,  dass das Kupplungsgemisch auf Kongorot  papier schwach sauer reagiert.

   Die Tempera  tur des Kupplungsgemisches     wird    während  der     Kupphing    durch Zugabe der nötigen  Menge Eis auf 0 bis 50 C gehalten. Nach der  vollständigen Zugabe der     Diazolösung    wird  das Gemisch durch Zugabe von     wässrigem          Natriumhydroxyd        lackmusalkalisch    gestellt.  Der Farbstoff wird     abfiltriert    und getrocknet.  



  Der schwefelsaure Ester des     N-ss-Oxy-          äthyl-N-ss'-p-tolyläthylanilins    wird durch Be  handeln von     N-ss-Oxyäthyl-N-ss'-p-tolyläthyl-          anilin    mit     Chlorsulfonsäure    in     Tetrachlor-          äthan    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 da.ss one N-ss- Oxyäthy 1-N-ss'-p-tolylethylaniline, diazotized 2,6-dichloro-4-nitroaniline and a sulfuric implements funds together in such a way that

       da.ss 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-ßs-oxyethyl-N-ßs'-p-tolylethylaniline can either first be coupled with diazotized 2,6-dichloro-4-nitroaniline and then the coupling product can be converted into the corresponding sulfuric acid ester or sulfonate first and couple the product obtained with diazotized 2,6-diehlor-4-nitroaniline.



  The new dye forms a black powder, which is soluble in water to dissolve a light orange solution and in sulfuric acid to form a chocolate-brown solution. It dyes cellulose acetate artificial silk in orange tones.



  <I> Example: </I> 20.7 parts of 2,6-dichloro-4-nitroaniline are concentrated by gradually adding a solution of 6.9 parts of dry sodium nitrite in 148 parts. Sulfuric acid diazotized. The sulfuric acid solution is stirred for one to two hours and then added to a mixture of 400 parts of ice and 100 parts of water.

   The filtered solution of the diazo compound is gradually added to an ice-cold solution of 35.7 parts of the sodium salt of the sulfuric acid ester of N-ßs-oxyethyl 1-N-ßs'-p-tolylethylaniline in 400 parts of water. Simultaneously with the addition of the diazo solution, 40% strength aqueous sodium hydroxide solution is added to such an extent that the coupling mixture reacts slightly acidic on Congo red paper.

   The temperature of the coupling mixture is kept at 0 to 50 C by adding the necessary amount of ice during the Kupphing. After all of the diazo solution has been added, the mixture is made litmus-alkaline by adding aqueous sodium hydroxide. The dye is filtered off and dried.



  The sulfuric acid ester of N-ss-oxyethyl-N-ss'-p-tolylethylaniline is obtained by treating N-ss-oxyethyl-N-ss'-p-tolylethylaniline with chlorosulfonic acid in tetrachloroethane.

Claims (1)

PATEITAISPRUCH: Verfahren zur Herstellung eines neuen Monoazofarbstoffes, dadurch gekennzeichnet, da.ss man N-ss-Oxyäthyl-N-ss'-p-tolyläthylani- lin, diazotiertes 2,6-Dichlor-4-nitranilin und ein Sulfurierungsmittel miteinander der massen zur Umsetzung bringt, PATEITAISPRUCH: A process for the production of a new monoazo dye, characterized in that N-ß-oxyethyl-N-ßs'-p-tolylethylaniline, diazotized 2,6-dichloro-4-nitroaniline and a sulphurizing agent are used for the masses Implementation brings dass die Oxy- äthylgruppe in die entsprechende Schwefel säureestergruppe übergeführt wird und der Diazorest in die 4-Stellung zum tertiären Stickstoffatom eintritt. Der neue Farbstoff bildet ein schwarzes Pulver, welches in Wasser unter Bildung einer hellorangen Lösung und in Schwefel säure unter Bildung einer schokoladebraunen Lösung löslich ist. Er färbt Zelluloseacetat- kunstseide in orangen Farbtönen. " UNTERANSPRüCHE 1. 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. The new dye forms a black powder which is soluble in water to form a light orange solution and in sulfuric acid to form a chocolate-brown solution. It dyes cellulose acetate artificial silk in orange shades. "SUBClaims 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass N-ss-Oxyäthyl-N- ss'-p-tolyläthylanilin mit diazotiertem 2,6-Di- chlor-4-nitranilin gekuppelt und das Kupp lungsprodukt zum" entsprechenden Schwefel säureester sulfiert wird. 2. Process according to patent claim, characterized in that N-ss-oxyethyl-N-ss'-p-tolylethylaniline is coupled with diazotized 2,6-dichloro-4-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'-p-tolyläthylanüin sulfiert und das erzielte Produkt mit diazotiertem 2,6-Dichlor-4-ni- tranilin gekuppelt wird. Process according to patent claim, characterized in that N-ss-oxyethyl-N-ss'-p-tolyläthylanüin sulfated and the product obtained is coupled with diazotized 2,6-dichloro-4-nitraniline.
CH261274D 1944-08-28 1945-08-28 Process for the preparation of a new monoazo dye. CH261274A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB261274X 1944-08-28
CH252136T 1947-12-15

Publications (1)

Publication Number Publication Date
CH261274A true CH261274A (en) 1949-04-30

Family

ID=25729597

Family Applications (1)

Application Number Title Priority Date Filing Date
CH261274D CH261274A (en) 1944-08-28 1945-08-28 Process for the preparation of a new monoazo dye.

Country Status (1)

Country Link
CH (1) CH261274A (en)

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