CH268078A - Process for the preparation of an azo dye. - Google Patents

Process for the preparation of an azo dye.

Info

Publication number
CH268078A
CH268078A CH268078DA CH268078A CH 268078 A CH268078 A CH 268078A CH 268078D A CH268078D A CH 268078DA CH 268078 A CH268078 A CH 268078A
Authority
CH
Switzerland
Prior art keywords
sep
azo dye
red
preparation
dye
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellschaft Ciba
Original Assignee
Ciba Geigy
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 Ciba Geigy filed Critical Ciba Geigy
Publication of CH268078A publication Critical patent/CH268078A/en

Links

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
    • C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
    • C09B29/16—Naphthol-sulfonic acids
    • 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
    • C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
    • C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
    • C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
    • C09B29/3647—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms
    • C09B29/3652—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles
    • C09B29/366—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles containing hydroxy-1,2-diazoles, e.g. pyrazolone

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Optical Filters (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Investigating Or Analysing Biological Materials (AREA)

Description

  

  Verfahren zur Herstellung eines     Azofarbstoffes.     
EMI0001.0002     
  
    Es <SEP> wurde <SEP> gefunden, <SEP> dass <SEP> man <SEP> zu <SEP> einem
<tb>  wertvollen <SEP> Azofarbstoff <SEP> gelangt, <SEP> wenn <SEP> man
<tb>  diazotiertes <SEP> 2-Axnino-l-n-butyloxy-4-tertiär  amylbenzol <SEP> finit <SEP> 1-Oxyxiaplitlialin-3,8-clisulfon  säure <SEP> vereinigt.
<tb>  



  Der <SEP> neue <SEP> Farbstoff <SEP> bildet <SEP> ein <SEP> rotes <SEP> Pulver,
<tb>  das <SEP> sich <SEP> in <SEP> Wassei# <SEP> mit <SEP> roter <SEP> Farbe <SEP> löst <SEP> und
<tb>  Wolle <SEP> aus <SEP> saurein <SEP> Bade <SEP> in <SEP> roten <SEP> Tönen <SEP> färbt.
<tb>  



  Das <SEP> beim <SEP> vorliegenden <SEP> Verfahren <SEP> als <SEP> Aus  gangsstoff <SEP> dienende <SEP> 2-Aniino-l-n-butyloxy-l  tei-tiäraniylliexizol <SEP> lässt <SEP> sich <SEP> beispielsweise <SEP> her  stellen <SEP> durch <SEP> Nitrierung <SEP> von <SEP> 1-Oxy-4-t.ertiär.
<tb>  ,iniyllienzol, <SEP> Biityliei-iing <SEP> der <SEP> ydrosylgruppe
<tb>  und <SEP> Rednktion <SEP> des <SEP> Nitroätliei-s.
<tb>  



  Die <SEP> Diazotieru <SEP> ng <SEP> kann <SEP> naeli <SEP> bekannten,
<tb>  für <SEP> schwer <SEP> diazot.ierbare <SEP> Amine <SEP> üblichen <SEP> Me  thoden, <SEP> beispielsweise <SEP> in <SEP> Gegenwart <SEP> von <SEP> Al  kohol <SEP> oder <SEP> Essigsä <SEP> ure <SEP> durchgeführt <SEP> werden.
<tb>  



  Die <SEP> KUpplun <SEP> @g <SEP> erfolgt <SEP> mit <SEP> Vorteil <SEP> in <SEP> alka  lischem, <SEP> vorzugsweise, <SEP> alkaliearbonatalkali  schem <SEP> Alediuni.     
EMI0001.0003     
  
    <I>Beispiel:</I>
<tb>  23,.5 <SEP> Teile <SEP> ?-Aniino-l-n-butyloxy-4-tert.iäi#  anivlbenzol <SEP> werden <SEP> mit <SEP> 140 <SEP> Teilen <SEP> Äthylalko-       hol vermischt.

   Unterhalb     -I-   <B>100</B> werden 35  Teile     konz.    Salzsäure zugesetzt, und unterhalb       -I-    50 lässt man eine     konz.    wässerige Lösung  von 7,2 Teilen     Natriumnitrit        zutropfen.    Diese       Diazolösung    wird bei 01 mit, der Lösung von  3:5 Teilen des     Dinatriumsalzes    der     1-0xynapli-          tlialin-3,8-disulfoxisäui@e    in 330 Teilen einer       gesättigten        Natriumearbonatlösun-    vermischt.

         Naeli        eini--en    Stunden wird der rote Farbstoff  nach Zugabe von     Natriumehlorid        abfiltriert     und hierauf in heissem Wasser gelöst. Die Lö  sung wird     geklärt    und mit so viel     Natrium-          ehlorid        versetzt,        class    der Farbstoff zum gröss  ten Teil wieder ausgefällt     wird.        Ilierauf    wird  der Farbstoff     abfiltriert    und     syetroeknet.  



  Process for the preparation of an azo dye.
EMI0001.0002
  
    <SEP> was found <SEP>, <SEP> that <SEP> man <SEP> to <SEP> one
<tb> valuable <SEP> azo dye <SEP> gets, <SEP> if <SEP> man
<tb> diazotized <SEP> 2-axnino-l-n-butyloxy-4-tertiary amylbenzene <SEP> finite <SEP> 1-oxyxiaplitlialin-3,8-clisulfonic acid <SEP> combined.
<tb>



  The <SEP> new <SEP> dye <SEP> forms <SEP> a <SEP> red <SEP> powder,
<tb> the <SEP> <SEP> in <SEP> Wassei # <SEP> with <SEP> red <SEP> color <SEP> <SEP> and
<tb> Wool <SEP> from <SEP> acidic <SEP> bath <SEP> in <SEP> red <SEP> tones <SEP> dyes.
<tb>



  The <SEP> in the <SEP> present <SEP> method <SEP> as <SEP> starting material <SEP> serving <SEP> 2-aniino-ln-butyloxy-1-tiäraniylliexizol <SEP> can be <SEP> < SEP> e.g. <SEP> produce <SEP> through <SEP> nitration <SEP> of <SEP> 1-oxy-4-tertiary.
<tb>, iniyllienzol, <SEP> Biityliei-iing <SEP> of the <SEP> ydrosyl group
<tb> and <SEP> Rednction <SEP> of the <SEP> Nitroätliei-s.
<tb>



  The <SEP> diazotization <SEP> ng <SEP> can <SEP> naeli <SEP> known,
<tb> for <SEP> difficult <SEP> diazotizable <SEP> amines <SEP> common <SEP> methods, <SEP> for example <SEP> in <SEP> presence <SEP> of <SEP> alcohol < SEP> or <SEP> acetic acid <SEP> ure <SEP> are carried out <SEP>.
<tb>



  The <SEP> KUpplun <SEP> @g <SEP> takes place <SEP> with <SEP> advantage <SEP> in <SEP> alkaline, <SEP> preferably, <SEP> alkali carbonate alkaline <SEP> alediuni.
EMI0001.0003
  
    <I> Example: </I>
<tb> 23, .5 <SEP> parts <SEP>? -aniino-ln-butyloxy-4-tert.iäi # anivlbenzol <SEP> are <SEP> with <SEP> 140 <SEP> parts <SEP> ethyl alcohol- get mixed.

   Below -I- <B> 100 </B> 35 parts of conc. Hydrochloric acid is added, and below -I- 50 a conc. add dropwise aqueous solution of 7.2 parts of sodium nitrite. This diazo solution is mixed at 01 with the solution of 3: 5 parts of the disodium salt of 1-oxynapli- tlialin-3,8-disulfoxisäui @ e in 330 parts of a saturated sodium carbonate solution.

         After adding sodium chloride, the red dye is filtered off for one hour and then dissolved in hot water. The solution is clarified and enough sodium chloride is added so that most of the dye is precipitated again. The dye is then filtered off and syetroeknet.

Claims (1)

P ATENT ANSPRUCII: Verfahren zur Herstellung eines Azofarb- stoffes, dadurch gekennzeichnet, dass man di- azotiertes 2-A.mino-l-n-buty loxy-4-tertiä.ramy 1- benzol mit 1.-Oxynaphthaliii-3,8-disulfonsäure vereinigt. Der neue Farbstoff bildet ein rotes Pulver, das sieh in Wasser mit roter Farbe löst und olle aus saurem Bade in roten. Tönen färbt. P ATENT ANSPRUCII: Process for the production of an azo dye, characterized in that diazo-in-butyloxy-4-tertiary-ramy 1-benzene is mixed with 1.-oxynaphthalene-3,8-disulfonic acid united. The new dye forms a red powder that dissolves in water with a red color and turns red from an acid bath. Tones colors.
CH268078D 1947-04-30 1947-04-30 Process for the preparation of an azo dye. CH268078A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH262279T 1947-04-30
CH268078T 1947-04-30

Publications (1)

Publication Number Publication Date
CH268078A true CH268078A (en) 1950-04-30

Family

ID=25730566

Family Applications (1)

Application Number Title Priority Date Filing Date
CH268078D CH268078A (en) 1947-04-30 1947-04-30 Process for the preparation of an azo dye.

Country Status (1)

Country Link
CH (1) CH268078A (en)

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