CH195863A - Process for the preparation of a dye of the naphthalene-1.4.5.8-tetracarboxylic acid series. - Google Patents

Process for the preparation of a dye of the naphthalene-1.4.5.8-tetracarboxylic acid series.

Info

Publication number
CH195863A
CH195863A CH195863DA CH195863A CH 195863 A CH195863 A CH 195863A CH 195863D A CH195863D A CH 195863DA CH 195863 A CH195863 A CH 195863A
Authority
CH
Switzerland
Prior art keywords
dye
tetracarboxylic acid
naphthalene
acid series
preparation
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellsc Farbenindustrie
Original Assignee
Ig Farbenindustrie Ag
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 Ig Farbenindustrie Ag filed Critical Ig Farbenindustrie Ag
Publication of CH195863A publication Critical patent/CH195863A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/06—Peri-condensed systems
    • 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
    • C09B49/00—Sulfur dyes
    • C09B49/12—Sulfur dyes from other compounds, e.g. other heterocyclic compounds
    • C09B49/124—Sulfur dyes from other compounds, e.g. other heterocyclic compounds from polycarbocyclic compounds

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Description

  

  <B>Zusatzpatent</B>     zum        Hauptpatent    Nr. 191853.    Verfahren zur Herstellung eines Farbstoffes der     Naphthalin-1.        4.5.8-tetrakarbon-          säurereihe.       Gegenstand dieses Zusatzpatentes ist ein  Verfahren zur Herstellung eines     Farbstoffes     der     Naphthalin-1        .4.5.8-tetrakarbonsäure-          reihe,    welches dadurch gekennzeichnet ist,

    dass man     2.6-Dichlornaphthalin-1.4.5.8-          tetrakarbonsäureanhydrid    mit Anilin unter  Halogenaustausch zur Umsetzung bringt und  den so erhaltenen Stoff mit einem     sulfierend     wirkenden Mittel behandelt.  



  <I>Beispiel:</I>  8,5 Gewichtsteile 2.     6-Dichlornaphthalin-          1.4.5.8-tetrakarbonsäureanhydrid        (vergl.     Beispiel des Hauptpatentes) werden unter  Rühren mit 100 Gewichtsteilen Anilin bis  zum schwachen Sieden erhitzt. Bereits in der  Hitze scheidet sich ein Teil des Umsetzungs  produktes in dunkeln metallglänzenden Na  deln ab. Man verdünnt das Reaktionsgemisch  mit 100 Gewichtsteilen Alkohol, saugt noch  warm ab, wäscht mit Alkohol nach und  locht den Rückstand mit angesäuertem    Wasser aus und trocknet. Es werden so  <B>13,5</B> Gewichtsteile 2.     6-Dianilino-naphtbaliii-          1.4.5.8-tetrakarbonsäurediphenylimid    er  halten.

   Dieser Stoff kristallisiert in langen  dunkelblauen, metallglänzenden, oberhalb  4000 C schmelzenden Nadeln. Das Produkt  wird dann zum Beispiel durch Verrühren bei  Raumtemperatur mit 15facher Gewichtsmenge       Schwefelsäuremonohydrat        sulfiert,    wobei zwei       Sulfonsäuregruppen    in das Molekül eintreten,  und es wird so ein Wollfarbstoff erhalten,  welcher Wolle in blauen Tönen von guter  Echtheit färbt.  



  Zu dem gleichen Produkt in gleicher  Reinheit aber geringerer Ausbeute gelangt  man, wenn man, statt von reinem 2.     6-Dichlor-          naphthalintetrakarbonsäureanhydrid    auszuge  hen, das Gemisch von vermutlich<B>2.6-</B> und  2.     7-Dichlornaphthalin-1.    4. 5 .     8-tetrakarbon-          säure    anwendet, welches beim     ogydativen     Abbau des im Schweizer Patent 172066 und       Zusatz    beschriebenen     Hexachlorpyrens    nach      dem Verfahren des Schweizer Patentes 169347  und Zusätzen entsteht.



  <B> Additional patent </B> to main patent no. 191853. Process for the production of a naphthalene-1 dye. 4.5.8-tetracarboxylic acid series. The subject of this additional patent is a process for the production of a dye of the naphthalene-1 .4.5.8-tetracarboxylic acid series, which is characterized by

    that 2,6-dichloronaphthalene-1.4.5.8-tetracarboxylic acid anhydride is reacted with aniline with halogen exchange and the substance thus obtained is treated with a sulphurizing agent.



  <I> Example: </I> 8.5 parts by weight of 2. 6-dichloronaphthalene-1.4.5.8-tetracarboxylic acid anhydride (see example of the main patent) are heated to a gentle boil with 100 parts by weight of aniline while stirring. Even in the heat, part of the reaction product is deposited in dark, shiny metal needles. The reaction mixture is diluted with 100 parts by weight of alcohol, filtered off with suction while still warm, washed with alcohol and the residue perforated with acidified water and dried. There are thus <B> 13.5 </B> parts by weight of 2. 6-dianilino-naphtbaliii- 1.4.5.8-tetracarboxylic acid diphenylimide.

   This substance crystallizes in long, dark blue, shiny metal needles that melt above 4000 C. The product is then sulfated, for example, by stirring at room temperature with 15 times the amount by weight of sulfuric acid monohydrate, two sulfonic acid groups entering the molecule, and a wool dye is thus obtained which dyes wool in blue shades of good fastness.



  The same product in the same purity but lower yield is obtained if, instead of starting from pure 2,6-dichloronaphthalenetetracarboxylic acid anhydride, the mixture of presumably 2,6- and 2,7-dichloronaphthalene-1 is obtained . 4. 5. 8-tetracarboxylic acid is used, which is produced during the ogydative degradation of the hexachloropyrene described in Swiss patent 172066 and additive according to the process of Swiss patent 169347 and additives.

Claims (1)

PATE1i TAN SPR ITCH Verfahren zur Herstellung eines Farb stoffes der Naphthalin-1 . 4. 5. 8-tetrakarbon- säurereihe, dadureh gekennzeichnet, dass man 2. 6-Dichlornaphthaliri-1 . 4. 5 . 8-tetrakarbon- säureanhydrid mit Anilin unter Halogenaus tausch zur Umsetzung bringt und den so erhaltenen Stoff mit einem sulfierend wirken den Mittel behandelt. PATE1i TAN SPR ITCH Process for the production of a naphthalene-1 dye. 4. 5. 8-tetracarboxylic acid series, marked by the fact that 2. 6-dichloronaphthaliri-1. 4. 5. 8-tetracarboxylic acid anhydride with aniline under halogen exchange for conversion and the substance thus obtained is treated with a sulphurizing agent. Die so erhaltene Farbstoffdisulfosäuire färbt Wolle in blauen Tönen von sehr guter Echtheit. UNTERANSPRÜCHE: 1. Verfahren nach Patentanspruch, dadurch gekennzeichnet; dass man 2.6-Diehlor- naphthalin-1 . 4 . 5 . 8-tetrakarbonsäurean- hydrid mit überschüssigem Anilin bis zum schwachen Sieden erhitzt. 2. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass die Sulfierung durch Verrühren des Farbstoffes mit der 15fachen Gewichtsmenge Schwefelsäui-emonohydrat bei Raumtemperatur bewirkt wird. The dye disulfonic acid obtained in this way dyes wool in blue shades of very good fastness. SUBClaims: 1. Method according to claim, characterized; that you get 2,6-Diehlornaphthalin-1. 4th 5. 8-tetracarboxylic acid anhydride heated to a gentle boil with excess aniline. 2. The method according to claim, characterized in that the sulphonation is effected by stirring the dye with 15 times the amount by weight of sulfuric acid monohydrate at room temperature.
CH195863D 1936-03-03 1936-03-03 Process for the preparation of a dye of the naphthalene-1.4.5.8-tetracarboxylic acid series. CH195863A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH195863T 1936-03-03
CH191853T 1936-03-03

Publications (1)

Publication Number Publication Date
CH195863A true CH195863A (en) 1938-02-15

Family

ID=25722192

Family Applications (1)

Application Number Title Priority Date Filing Date
CH195863D CH195863A (en) 1936-03-03 1936-03-03 Process for the preparation of a dye of the naphthalene-1.4.5.8-tetracarboxylic acid series.

Country Status (1)

Country Link
CH (1) CH195863A (en)

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