CH267878A - Process for the preparation of an acidic dye of the anthraquinone series. - Google Patents

Process for the preparation of an acidic dye of the anthraquinone series.

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Publication number
CH267878A
CH267878A CH267878DA CH267878A CH 267878 A CH267878 A CH 267878A CH 267878D A CH267878D A CH 267878DA CH 267878 A CH267878 A CH 267878A
Authority
CH
Switzerland
Prior art keywords
blue
dye
anthraquinone
good
preparation
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 CH267878A publication Critical patent/CH267878A/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
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/16—Amino-anthraquinones
    • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
    • C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
    • C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
    • C09B1/34—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups sulfonated
    • C09B1/343—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups sulfonated only sulfonated in the anthracene nucleus

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

Description

  

      Zusatzpatent    zum Hauptpatent     Nr.    263286.    Verfahren zur Herstellung eines sauren Farbstoffes der     Anthrachinonreihe.       Es wurde gefunden, dass man neue     An-          thrachinonfarbstoffe    dadurch herstellen kann,  dass man     Anthraehinonverbindungen    der all  gemeinen Formel  
EMI0001.0007     
    worin X Halogen oder     Sulfo,    Y Halogen und  Z Wasserstoff oder     Sulfo    bedeuten, mit     aro-          matisehen    Aminen der allgemeinen Formel  
EMI0001.0012     
    worin R ein     Arylkern    und     R,

      Wasserstoff  oder     Alkyl    bedeuten, kondensiert, und wenn  X ein Halogenatom bedeutet, dieses in übli  cher Weise durch eine     Sulfogruppe    ersetzt.  



  Die so gewonnenen Farbstoffe färben ani  malische Fasern in blauen Tönen an, die gute  Licht- und     Nasseelitheit    besitzen und sich von  den Farbstoffen gemäss der     sehweiz.    Patent  selirift     Nr.    150808 und dem U. S.     A.-Patent     Nr. 1927125 besonders durch eine stark ge  steigerte     Walkechtheit    unterscheiden.  



  Zur Herstellung dieser Farbstoffe werden  als     aroylierte    aromatische     Aminoverbindun-          gen    zum Beispiel o-, in-,     p-Benzoylamino-ani-          lin;    o-, m-, p-(o'-Chlorbenzoyl-methylamino)-         anhin;    o-, m-,     p-(p'-Toluyl-äthylamino)-ani-          lin;    o-, m-,     p-(m'-Phenyl-benzoyl-butyl-amino)-          m-,    -p-,     -o-toluidin;    o-, m-,     p-Benzoylamino-in-,     -p-,     -o-ehloranilin    und viele andere mehr ver  wendet.  



  Das vorliegende Patent betrifft ein Ver  fahren     zur    Herstellung eines neuen sauren  Farbstoffes der     Anthrachinonreihe    und ist     i    da  durch gekennzeichnet, dass man     1-amino-4-          brom-anthrachinon-2-sulfonsaures    Natrium  mit     m-Aminobenzanilid    kondensiert.  



  Im folgenden Beispiel bedeuten Teile Ge  wichtsteile.  



  <I>Beispiel:</I>  20,2 Teile     1-amino-4-brom-anthraehinon-2-          sulfonsaures    Natrium, 15,9 Teile     m-Amino-          benzanilid,    8 Teile     Natriumbikarbonat,    0,4  Teile Kupferbronze, 60 Teile Äthanol und 120  Teile Wasser werden unter Rühren während  drei Stunden auf 700 erhitzt.  



  Die blau gewordene Kondensationsmasse  wird auf übliche Weise aufgearbeitet und lie  fert nach dem Trocknen ein blaues Farbstoff  pulver, das sich in warmem Wasser klar blau  löst. Die Farbe der Lösung in konzentrierter  Schwefelsäure ist hell blaugrün, beim Zusatz  von wenig     Paraformaldehyd    tritt ein Um  schlag nach     tiefgrasgrün    ein. Der neue Farb  stoff färbt Wolle, Seide und andere tierische  Fasern sowie künstliche Fasern, wie z. B.  Nylon, in schönen blauen Tönen an. Die Fär  bungen sind von guter Lichtechtheit, sehr  guter Wasch- und Schweissechtheit und guter       Walkechtheit.  



      Additional patent to main patent No. 263286. Process for the production of an acidic dye of the anthraquinone series. It has been found that new anthraquinone dyes can be prepared by using anthraquinone compounds of the general formula
EMI0001.0007
    wherein X is halogen or sulfo, Y is halogen and Z is hydrogen or sulfo, with aromatic amines of the general formula
EMI0001.0012
    where R is an aryl nucleus and R,

      Denotes hydrogen or alkyl, condensed, and when X denotes a halogen atom, this is replaced by a sulfo group in a customary manner.



  The dyes obtained in this way dye ani malic fibers in blue tones, which have good light and wet elicity and differ from the dyes according to the sehweiz. Patent selirift no. 150808 and the U.S.A. patent no. 1927125 differ particularly through a greatly increased flexing fastness.



  To produce these dyes, the aroylated aromatic amino compounds, for example, o-, in-, p-benzoylamino-aniline; o-, m-, p- (o'-chlorobenzoyl-methylamino) - anhin; o-, m-, p- (p'-toluylethylamino) aniline; o-, m-, p- (m'-phenyl-benzoyl-butyl-amino) -m-, -p-, -o-toluidine; o-, m-, p-Benzoylamino-in, -p-, -o-ehloraniline and many others are used.



  The present patent relates to a process for the production of a new acidic dye of the anthraquinone series and is characterized in that 1-amino-4-bromo-anthraquinone-2-sulfonic acid sodium is condensed with m-aminobenzanilide.



  In the following example, parts mean parts by weight.



  <I> Example: </I> 20.2 parts of 1-amino-4-bromo-anthraquinone-2-sulfonic acid sodium, 15.9 parts of m-aminobenzanilide, 8 parts of sodium bicarbonate, 0.4 part of copper bronze, 60 parts Ethanol and 120 parts of water are heated to 700 for three hours while stirring.



  The condensation mass, which has turned blue, is worked up in the usual way and, after drying, delivers a blue dye powder that dissolves in warm water to give a clear blue color. The color of the solution in concentrated sulfuric acid is light blue-green; if a little paraformaldehyde is added, it changes to deep grass green. The new dye dyes wool, silk and other animal fibers as well as artificial fibers such as. B. Nylon, in beautiful blue tones. The dyeings are of good lightfastness, very good fastness to washing and perspiration and good fastness to milled.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines sauren Farbstoffes der Anthrachinonreihe, dadurch gekennzeichnet, dass man 1-amino-4-brom-an- thrachinon-2-sulfonsaures Natrium mit m- Aminobenzanilid kondensiert. Der Farbstoff ist ein blaues Pulver, das sich in warmem Wasser klar blau löst. Die Farbe der Lösung in konzentrierter Schwefel säure ist hell blaugrün; beim Zusatz von wenig Paraformaldehy d tritt ein Umschlag nach tief grasgrün ein. Claim: Process for the preparation of an acidic dye of the anthraquinone series, characterized in that 1-amino-4-bromo-anthraquinone-2-sulfonic acid sodium is condensed with m-aminobenzanilide. The dye is a blue powder that dissolves clear blue in warm water. The color of the solution in concentrated sulfuric acid is light blue-green; with the addition of a little paraformaldehyde, a change to deep grass-green occurs. Der neue Farbstoff färbt Wolle, Seide und andere tierische Fasern sowie künstliche Fa- sern, wie z. E. Nylon, in schönen blauen Tönen an. Die Färbungen sind von guter Lichtecht heit, sehr guter Wasch- und Schweisseehtbeit und guter Walkechtheit. Er besitzt. die Formel. EMI0002.0012 The new dye dyes wool, silk and other animal fibers as well as artificial fibers such as E. Nylon, in beautiful blue tones. The dyeings are of good lightfastness, very good washability and perspiration and good millfastness. He owns. the formula. EMI0002.0012
CH267878D 1947-06-25 1947-06-25 Process for the preparation of an acidic dye of the anthraquinone series. CH267878A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH263286T 1947-06-25
CH267878T 1947-06-25

Publications (1)

Publication Number Publication Date
CH267878A true CH267878A (en) 1950-04-15

Family

ID=25730639

Family Applications (1)

Application Number Title Priority Date Filing Date
CH267878D CH267878A (en) 1947-06-25 1947-06-25 Process for the preparation of an acidic dye of the anthraquinone series.

Country Status (1)

Country Link
CH (1) CH267878A (en)

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