CH190154A - Process for the preparation of a complexed metal-containing dye. - Google Patents

Process for the preparation of a complexed metal-containing dye.

Info

Publication number
CH190154A
CH190154A CH190154DA CH190154A CH 190154 A CH190154 A CH 190154A CH 190154D A CH190154D A CH 190154DA CH 190154 A CH190154 A CH 190154A
Authority
CH
Switzerland
Prior art keywords
copper
dye
parts
glycocolla
preparation
Prior art date
Application number
Other languages
German (de)
Inventor
Gesellschaft Fuer Chemis Basel
Original Assignee
Chem Ind Basel
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 Chem Ind Basel filed Critical Chem Ind Basel
Publication of CH190154A publication Critical patent/CH190154A/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
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/02—Hydroxy-anthraquinones; Ethers or esters thereof
    • C09B1/06—Preparation from starting materials already containing the anthracene nucleus
    • C09B1/12—Dyes containing sulfonic acid groups
    • 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
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/06—Hydroxy derivatives of triarylmethanes in which at least one OH group is bound to an aryl nucleus and their ethers or esters
    • 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
    • C09B45/01—Complex metal compounds of azo dyes characterised by the method of metallisation
    • 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
    • C09B45/18—Monoazo compounds containing copper
    • 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
    • C09B45/48—Preparation from other complex metal compounds of azo dyes
    • 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
    • C09B61/00—Dyes of natural origin prepared from natural sources, e.g. vegetable sources

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Treatment And Processing Of Natural Fur Or Leather (AREA)

Description

  

  Verfahren zur Herstellung eines komplex gebundenes Metall enthaltenden     Farbstoffes.       Es wurde gefunden, dass ein komplex     ge-          bundenes    Metall enthaltender Farbstoff her  gestellt werden kann, wenn man den     Azo-          farbstoff    der Formel  
EMI0001.0006     
    ein kupferabgebendes Mittel und     Glykokoll     aufeinander einwirken lässt.  



  Der erhaltene Farbstoff stellt ein dunkel  gefärbtes, in Wasser leicht lösliches Pulver  dar. Wird die wässerige Lösung auf eine       Aluminiumsulfatschwerspat-Substratbasis    ge  fällt, so wird ein     violettbraunes,    lichtechtes  Pigment erhalten.  



  Eine zweckmässige Ausführungsform des  Verfahrens besteht darin, dass zuerst durch  Umsetzung von     Glykokoll    mit einem kupfer-    abgebenden Mittel das Kupfersalz des     Glyko-          kolls    hergestellt und letzteres mit dem     Azo-          farbstoff    umgesetzt wird;     Glykokollkupfer          hydrolysiert    in alkalischer Lösung nicht oder  nur wenig und     kann    deshalb in alkalischen  Medien zur Anwendung gelangen.  



  Im ferneren kann das Verfahren auch  derart durchgeführt werden, dass auf den       Fa.rbs@toff,    der     unter        Verwendung    der übli  chen kupferabgebenden Mittel, wie z. B.  Kupfersulfat, in die Kupferverbindung über  geführt worden ist,     Glykokoll    einwirken ge  lassen wird.  



  <I>Beispiel 1:</I>  5 Teile des     Azofarbstoffes    aus     diazotier-          ter        6-Nitro-2-amino-l-phenol    - 4 -     sulfonsäure     und     2-Oxynaphthalin    werden     in    100 Teilen  Wasser gelöst und bei 80   mit einer Lösung  von 2,5 Teilen     Glykokollkupfer            [Cu(NHZCHzC00)2,    1     H20]       in 20 Teilen Wasser versetzt.

   Es bildet sich  sofort die komplexe Glykokollkupferverbin-           dung,    die, im     Gegensatze    zu den mit den       üblichen        Kupferungsmitteln    hergestellten  Kupferkomplexen, leicht löslich ist. Durch  Zugabe von Kochsalz zur Lösung der kom  plexen     Glykokollkupferverbindung    wird diese  ausgefällt; sie wird filtriert und getrocknet.  <I>Beispiel 2:</I>  4 Teile des in Beispiel 1 verwendeten       Azofarbstoffes    werden in 100 Teilen Wasser  bei 80 bis 90   gelöst. Man setzt eine Lösung  von 2,5 Teilen kristallisiertem Kupfersulfat  in 10 Teilen Wasser zu und rührt einige Zeit.

    Es bildet sich ein kristalliner, schwer lös  licher Niederschlag der     Kupferkomplexver-          bindung    des Farbstoffes. Der Niederschlag  wird filtriert, in 50 Teilen Wasser von 40    aufgeschlämmt und mit 2 Teilen     Glykokoll     und 1 Teil     calc.    Soda versetzt. Die     Glyko-          kollkupferkomplexverbindung    des Farbstof  fes geht mit violetter Farbe in Lösung und  wird mittels Kochsalz daraus abgeschieden.  <I>Beispiel 3:</I>  4 Teile des in Beispiel 1 und 2 verwen  deten     Azofarbstoffes    werden in     100    Tei  len Wasser bei 85 bis 95   gelöst.

   Man setzt  darauf 2,5 Teile     glykokollsaures    Natrium  und hierauf eine Lösung von 2,5 Teilen kri  stallisiertem Kupfersulfat in 10 Teilen Was  ser zu. Es bildet sich sofort die violette Lö  sung der     Komplexverbindung    des Farbstof  fes; diese wird durch     Beigabe    von Kochsalz  abgeschieden.



  Process for the preparation of a complexed metal-containing dye. It has been found that a complex-bonded metal-containing dye can be produced by using the azo dye of the formula
EMI0001.0006
    a copper-releasing agent and glycocolla can interact.



  The dye obtained is a dark-colored powder which is readily soluble in water. If the aqueous solution is deposited on an aluminum sulfate barite substrate, a violet-brown, lightfast pigment is obtained.



  An expedient embodiment of the process consists in that the copper salt of the glycol is first produced by reacting glycoll with a copper-releasing agent and the latter is reacted with the azo dye; Glycocopper does not hydrolyze or only slightly hydrolyzes in alkaline solution and can therefore be used in alkaline media.



  Furthermore, the process can also be carried out in such a way that on the Fa.rbs@toff, who uses the usual copper-releasing agents, such as. B. copper sulfate, in the copper compound has been passed over, glycocoll is allowed to act.



  <I> Example 1: </I> 5 parts of the azo dye from diazotized 6-nitro-2-amino-1-phenol - 4 - sulfonic acid and 2-oxynaphthalene are dissolved in 100 parts of water and at 80 with a solution of 2.5 parts of glycocolla copper [Cu (NHZCHzC00) 2, 1 H20] are added to 20 parts of water.

   The complex glycocopper compound is formed immediately, which, in contrast to the copper complexes produced with the usual copper plating agents, is easily soluble. By adding common salt to the solution of the complex glycocopper compound, this is precipitated; it is filtered and dried. Example 2: 4 parts of the azo dye used in Example 1 are dissolved in 100 parts of water at 80 to 90 degrees. A solution of 2.5 parts of crystallized copper sulfate in 10 parts of water is added and the mixture is stirred for some time.

    A crystalline, poorly soluble precipitate of the copper complex compound of the dye forms. The precipitate is filtered off, slurried in 50 parts of water of 40 and with 2 parts of glycocolla and 1 part of calc. Soda added. The glycol copper complex compound of the dye goes into solution with a violet color and is separated out from it using common salt. <I> Example 3: </I> 4 parts of the azo dye used in Examples 1 and 2 are dissolved in 100 parts of water at 85 to 95.

   It is 2.5 parts of sodium glycollate and then a solution of 2.5 parts of crystallized copper sulfate in 10 parts of water. The violet solution of the complex compound of the dye forms immediately; this is deposited by adding table salt.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines komplex gebundenes Metall enthaltenden Farbstoffes, dadurch gekennzeichnet, dass man den Azo- farbstoff der Formel EMI0002.0020 ein kupferabgebendes Mittel und Glykokoll aufeinander einwirken lässt. Der erhaltene Farbstoff stellt ein dunkel gefärbtes, in Wasser leicht lösliches Pulver dar. Wird die wässerige Lösung auf eine Aluminiumsulfatsehwerspat-Substratbasis ge fällt, so wird ein violettbraunes, lichtechtes Pigment erhalten. <B>UNTERANSPRÜCHE:</B> 1. PATENT CLAIM: Process for the preparation of a complex-bonded metal-containing dye, characterized in that the azo dye of the formula EMI0002.0020 a copper-releasing agent and glycocolla can interact. The dye obtained is a darkly colored powder which is readily soluble in water. If the aqueous solution is deposited on an aluminum sulfate spar substrate, a violet-brown, lightfast pigment is obtained. <B> SUBClaims: </B> 1. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man das Kupfersalz des Glykokolls auf den Azofarbstoff ein wirken lässt. 2. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man den Azofarb- stoff der Formel EMI0002.0028 unter Verwendung kupferabgebender Mit tel in die komplexe Kupferverbindung überführt und auf letztere Glykokoll ein wirken lässt. Process according to claim, characterized in that the copper salt of the glycocolla is allowed to act on the azo dye. 2. The method according to claim, characterized in that the azo dye of the formula EMI0002.0028 converted into the complex copper compound using copper-releasing agents and allowing the latter to act on the glycocolla.
CH190154D 1936-02-27 1936-02-27 Process for the preparation of a complexed metal-containing dye. CH190154A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH190154T 1936-02-27
GB6685/36A GB470356A (en) 1936-02-27 1936-03-05 Manufacture of dyestuffs containing metal in complex union

Publications (1)

Publication Number Publication Date
CH190154A true CH190154A (en) 1937-04-15

Family

ID=9818927

Family Applications (7)

Application Number Title Priority Date Filing Date
CH193237D CH193237A (en) 1936-02-27 1936-02-27 Process for the preparation of a complexed metal-containing dye.
CH193241D CH193241A (en) 1936-02-27 1936-02-27 Process for the preparation of a complexed metal-containing dye.
CH190154D CH190154A (en) 1936-02-27 1936-02-27 Process for the preparation of a complexed metal-containing dye.
CH193238D CH193238A (en) 1936-02-27 1936-02-27 Process for the preparation of a complexed metal-containing dye.
CH193242D CH193242A (en) 1936-02-27 1936-02-27 Process for the preparation of a complexed metal-containing dye.
CH193243D CH193243A (en) 1936-02-27 1936-02-27 Process for the preparation of a complexed metal-containing dye.
CH193244D CH193244A (en) 1936-02-27 1936-02-27 Process for the preparation of a complexed metal-containing dye.

Family Applications Before (2)

Application Number Title Priority Date Filing Date
CH193237D CH193237A (en) 1936-02-27 1936-02-27 Process for the preparation of a complexed metal-containing dye.
CH193241D CH193241A (en) 1936-02-27 1936-02-27 Process for the preparation of a complexed metal-containing dye.

Family Applications After (4)

Application Number Title Priority Date Filing Date
CH193238D CH193238A (en) 1936-02-27 1936-02-27 Process for the preparation of a complexed metal-containing dye.
CH193242D CH193242A (en) 1936-02-27 1936-02-27 Process for the preparation of a complexed metal-containing dye.
CH193243D CH193243A (en) 1936-02-27 1936-02-27 Process for the preparation of a complexed metal-containing dye.
CH193244D CH193244A (en) 1936-02-27 1936-02-27 Process for the preparation of a complexed metal-containing dye.

Country Status (3)

Country Link
CH (7) CH193237A (en)
FR (1) FR818329A (en)
GB (1) GB470356A (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3399186A (en) * 1962-01-24 1968-08-27 Kanegafuchi Spinning Co Ltd Cationic metal-containing azo dyes from 8-hydroxyquinoline
CH618728A5 (en) 1975-11-18 1980-08-15 Ciba Geigy Ag
LU83177A1 (en) * 1981-02-27 1982-09-10 Oreal USE OF HYDROXYANTHRAQUINONES FOR COLORING HUMAN KERATINIC FIBERS, METHOD AND COMPOSITION USING THE SAME
US4901824A (en) * 1984-12-12 1990-02-20 Shimano Industrial Company Limited Bicycle brake shoe having slit surfaces
LU86422A1 (en) * 1986-05-07 1987-12-16 Oreal PROCESS FOR DYEING HUMAN HAIR WITH BRASILINE OR ITS HYDROXYL DERIVATIVE AND COMPOSITIONS IMPLEMENTED
CN116376312A (en) * 2023-03-31 2023-07-04 南通大学 High-temperature-resistant red vegetable dye and preparation method and application thereof

Also Published As

Publication number Publication date
CH193242A (en) 1937-09-30
CH193244A (en) 1937-09-30
CH193238A (en) 1937-09-30
GB470356A (en) 1937-08-13
CH193243A (en) 1937-09-30
CH193241A (en) 1937-09-30
CH193237A (en) 1937-09-30
FR818329A (en) 1937-09-24

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