CH275801A - Process for the preparation of a metallizable monoazo dye. - Google Patents

Process for the preparation of a metallizable monoazo dye.

Info

Publication number
CH275801A
CH275801A CH275801DA CH275801A CH 275801 A CH275801 A CH 275801A CH 275801D A CH275801D A CH 275801DA CH 275801 A CH275801 A CH 275801A
Authority
CH
Switzerland
Prior art keywords
dye
aminophenol
sulfonic acid
preparation
monoazo dye
Prior art date
Application number
Other languages
German (de)
Inventor
Ag Sandoz
Original Assignee
Ag Sandoz
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 Ag Sandoz filed Critical Ag Sandoz
Publication of CH275801A publication Critical patent/CH275801A/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
    • C09B45/00—Complex metal compounds of azo dyes
    • C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
    • C09B45/14—Monoazo compounds
    • C09B45/16—Monoazo compounds containing chromium
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/02—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes
    • D06P1/10—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes containing metal

Description

  

  Verfahren zur Herstellung eines     metallisierbaren        Monoazofarbstoffes.       Es wurde gefunden, dass man wertvolle       itietallisierbare        l@Ionoazofarbstoffe    erhält, wenn  man     diazotierte        2-Aniinoplienol-sulfonsäure-          amide    der allgemeinen Formel  
EMI0001.0008     
    worin     _X        Wasserstoff    oder Halogen und V       und    Z     Wasserstoff,        Alkyl,    Halogen,     -COOH,          S02NH2,

  -S02NH-Alkyloder        --S02-N-        -(alkyl).=     bedeuten, mit. einem     1-Acylamino-7-naphthol     kuppelt. Aus der grossen Anzahl der hierzu an  wendbaren     2-Aminophenolsulfamide    seien er  wähnt:

       2-Aminophenol-4-sulfonsäure-(2'-sulfo-          methylamido)        -anilid,        2-Aminophenol-4-sul-          fonsäure-        (2'-sulfodimethylamido)        -anilid,    2  Aminophenol-4-sulfonsäure-anilid,     2-Amino-          Iiheno1H4-sulfonsäure-anthranilid,        2-Aminophe-          nol-4rsulfonsäureryp-toluidid,        2-Aminophenol-4-          sulfonsäure-(3'-sulfami:

  do)-anilid,        2-Amino-          phenol-5-sulfonsäure-anthranilid,        4-Chlor-2-          aminophenol    - 5 -     sulfonsäure    -     antliranilid,    6   Chlor - 2 -     aminophenol-4-#sulfonsäure-anthrani-          lid,    2-Aminophenol-4-sulfonsäure-4'-chlor-3'-         earboxy-anilid,        2-Aminophenol-4-sulfonsäure-          3'-carboxy-anilid    und     2-Aminophenol-4-sulfon-          säure-4'-carboxyanilid.     



  Die auf übliche Weise erfolgende Kupp  lung der neuen     Diazokomponenten    mit den     1-          Acylamino-7-naphtholen    liefert die     Azofarb-          stoffe    in     guten    Ausbeuten.  



  Die nach diesem Verfahren dargestellten  Farbstoffe sind getrocknet und gemahlen dun  kelblaue Pulver,     welehe    sich in konzentrierter  Schwefelsäure mit     bläulichroter    Farbe lösen;  sie sind ausgezeichnete     Nachehromierungs-          farbstoffe;    die meisten von ihnen eignen sieh       vorzüglich    für das neutrale     Einbadchrom-          färbeverfahren.     



  Nach dem     Nachchromierungs-    oder dem       Einbadehromfärbeverfahren    auf Wolle ausge  färbt, liefern die neuen Farbstoffe schöne  graue, graublaue und blaue Töne von ausge  zeichneter Licht-, Wasch-, Walk- und     Karbo-          r-isierechtheit.     



  Gegenstand der vorliegenden Erfindung       ist    ein Verfahren zur Herstellung eines     metal-          lisierbaren        Monoa,zofarbstoffas,    welches da  durch gekennzeichnet ist, dass man     diazotier-          tes        2@Aminophenol-4-sulfonsäureanilid    mit     1-          (Adipinylamino)-7-naphthol    kuppelt.

      <I>Beispiel:</I>    26,4 Teile     2-Aminophenol-4-sulfonsäureani-          lid    werden mit 6,9 Teilen     Natriumnitrit    und  25 Teilen Salzsäure 30 %     diazotiert.    Die     aus-          geschiedene        Diazoverbindimg    wird     abfiltriert         und in eine eiskalte Lösung von 28,7 Teilen     1-          (Adipinylamino)-7-naphthol    und 30 Teilen       Natriumcaxbonat    in 200 Teilen Wasser einge  tragen.     -Nach    etwa 3 Stunden ist die Kupp  lung fertig.  



  Der auf übliche     Weise    isolierte neue     Mono-          azofarbstoff    ist ein dunkelblaues Pulver, wel  ches sich in konzentrierter     ,Schwefelsäure    mit  bordeauxroter Farbe löst. Er ist     ein    ausge  zeichneter     neutralziehender        Einbadchromfarb-          stoff    und gibt auf Wolle Ausfärbungen von  schönen grauen Tönen.



  Process for the preparation of a metallizable monoazo dye. It has been found that valuable itietallisable l @ ionoazo dyes are obtained if diazotized 2-Aniinoplienol-sulfonic acid amides of the general formula
EMI0001.0008
    where _X is hydrogen or halogen and V and Z are hydrogen, alkyl, halogen, -COOH, SO2NH2,

  -S02NH-alkyl or --S02-N- - (alkyl). =, With. a 1-acylamino-7-naphthol. From the large number of 2-aminophenol sulfamides that can be used for this purpose, the following should be mentioned:

       2-aminophenol-4-sulfonic acid (2'-sulfomethylamido) anilide, 2-aminophenol-4-sulfonic acid (2'-sulfodimethylamido) anilide, 2 aminophenol-4-sulfonic acid anilide, 2-amino - Iiheno1H4-sulfonic acid anthranilide, 2-aminophenol-4rsulfonsäureryp-toluidid, 2-aminophenol-4-sulfonic acid- (3'-sulfami:

  do) -anilide, 2-aminophenol-5-sulfonic acid-anthranilide, 4-chloro-2-aminophenol - 5 - sulfonic acid - antliranilide, 6 chlorine - 2 - aminophenol-4- # sulfonic acid-anthranilide, 2-aminophenol -4-sulfonic acid-4'-chloro-3'-earboxy-anilide, 2-aminophenol-4-sulfonic acid-3'-carboxy-anilide and 2-aminophenol-4-sulfonic acid-4'-carboxyanilide.



  The customary coupling of the new diazo components with the 1-acylamino-7-naphthols gives the azo dyes in good yields.



  The dyes produced by this process are dried and ground dark blue powder, which dissolve in concentrated sulfuric acid with a bluish red color; they are excellent reconstructive dyes; Most of them are ideally suited for the neutral single bath chrome dyeing process.



  Dyed onto wool using the post-chrome plating or single bathing process, the new dyes provide beautiful gray, gray-blue and blue tones with excellent light, wash, milled and carbonised fastness.



  The present invention relates to a process for the production of a metalizable mono, zo dye, which is characterized in that diazotized 2 @ aminophenol-4-sulfonic acid anilide is coupled with 1- (adipinylamino) -7-naphthol.

      <I> Example: </I> 26.4 parts of 2-aminophenol-4-sulfonic acid anilide are diazotized with 6.9 parts of sodium nitrite and 25 parts of 30% hydrochloric acid. The precipitated diazo compound is filtered off and carried into an ice-cold solution of 28.7 parts of 1- (adipinylamino) -7-naphthol and 30 parts of sodium carbonate in 200 parts of water. - The coupling is ready after about 3 hours.



  The new monoazo dye isolated in the usual way is a dark blue powder which dissolves in concentrated sulfuric acid with a burgundy red color. It is an excellent, neutral, single-bath chrome dye and gives beautiful gray tones on wool.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines metalli- sierbaren Monoazofarbstoffes. dadurch ge kennzeichnet, dass man dianotiertes 2-Amiiio- phenol-4-sulfonsä.ureanilid mit 1-(Adipin N-1- amino)-7-naphthol kuppelt.. Der neue Farbstoff ist ein dunkelblaues Pulver, welches sich in konzentrierter Sehwe- felsäure mit bordeauxroter Farbe löst. PATENT CLAIM: Process for the production of a metallizable monoazo dye. characterized in that dianotated 2-amiiiophenol-4-sulfonsä.ureanilid is coupled with 1- (adipin N-1- amino) -7-naphthol .. The new dye is a dark blue powder, which is concentrated in concentrated sehwe- dissolves rock acid with a burgundy color. Er ist ein ausgezeichneter neutralziehen.der Ein badchromfarbstoff und gibt auf Wolle Aus färbungen von schönen grauen Tönen. It is an excellent neutral dye, the bath chrome dye, and gives woolen dyes of beautiful gray tones.
CH275801D 1949-07-21 1949-07-21 Process for the preparation of a metallizable monoazo dye. CH275801A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH275801T 1949-07-21

Publications (1)

Publication Number Publication Date
CH275801A true CH275801A (en) 1951-06-15

Family

ID=4480416

Family Applications (1)

Application Number Title Priority Date Filing Date
CH275801D CH275801A (en) 1949-07-21 1949-07-21 Process for the preparation of a metallizable monoazo dye.

Country Status (1)

Country Link
CH (1) CH275801A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1061284B (en) * 1956-07-27 1959-07-16 Bayer Ag Process for dyeing structures made of polyterephthalic acid glycol esters

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1061284B (en) * 1956-07-27 1959-07-16 Bayer Ag Process for dyeing structures made of polyterephthalic acid glycol esters

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