CH314551A - Process for the preparation of a water-soluble and licensing azophthalocyanine dye - Google Patents

Process for the preparation of a water-soluble and licensing azophthalocyanine dye

Info

Publication number
CH314551A
CH314551A CH314551DA CH314551A CH 314551 A CH314551 A CH 314551A CH 314551D A CH314551D A CH 314551DA CH 314551 A CH314551 A CH 314551A
Authority
CH
Switzerland
Prior art keywords
acid
dye
water
azophthalocyanine
soluble
Prior art date
Application number
Other languages
German (de)
Inventor
Willy Dr Brentano
Original Assignee
Durand & Huguenin 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 Durand & Huguenin Ag filed Critical Durand & Huguenin Ag
Publication of CH314551A publication Critical patent/CH314551A/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
    • C09B47/00—Porphines; Azaporphines
    • C09B47/04—Phthalocyanines abbreviation: Pc
    • C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
    • C09B47/24—Obtaining compounds having —COOH or —SO3H radicals, or derivatives thereof, directly bound to the phthalocyanine radical
    • C09B47/26—Amide radicals
    • 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
    • C09B43/00—Preparation of azo dyes from other azo compounds
    • C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Coloring (AREA)

Description

  

  Verfahren     zur    Herstellung eines wasserlöslichen und     beizenziehenden          Azophthalocyaninfarbatoffes       Die vorliegende Erfindung betrifft ein  Verfahren zur Herstellung eines wasserlösli  chen     und        beizenziehenden        Azophthalocya.nin-          l'arbatoffes,    welches dadurch gekennzeichnet       ist,        class        man    1     Mol        11,

  5        %        Brom        enthaltendes          Kupferphthalocyanin    - 4,4', 4", 4"' -     tetrasulfo.-          ehlorid,    wie es erhältlich ist durch Einwir  kung von     Chlorsulfonsäure    auf     bromierte          Kupferphtha.locyanin    -     4,41,4",    4"' -     tetrasulfo        -          säure,    mit 1     Mol        3-Amino-4'-oxy-1,

  1'-azo-          benzol-5'-carbonsäure    und 2     Mol.        1,3-Dioxy-          benzol-4-carbonsäu        re    in Gegenwart einer Mi  neralsäure bindenden Substanz zur Um  setzung bringt.  



  Im übrigen gelten die im Hauptpatent er  wähnten     Ausführungen    hinsichtlich der vor  zugsweisen Durchführung des erfindungs  gemässen     Verfahrens.     



  Das     na.chstehendeBeispiel    erläutert das neue  Verfahren. Die angegebenen Teile bedeuten  Gewichtsteile.  



       Beispiel     64 Teile (1/20     Mol)        bromiert.es        Kupfer-          plithalocyanin-4,4',4",4"'-tetrasulfoehlorid,    er  halten durch Einwirkung von     Chlorsulfon-          säLLre    auf     bromierte        Kupferphthalocyanin-          4,4',4",4"'-sulfonsäure    (enthält gemäss     Ana-          lyse        11,5%        Brom),

          werden        auf        Eis        ausgela-          den,    das     abgesogene    Reaktionsprodukt mit  300 Teilen zerkleinertem Eis vermischt und  unter Rühren eine Lösung, enthaltend 19,8    Teile     (1/10        Mol)    des     Dinatriumsalzes    der       1,3-Dioxybenzol-4-carbonsäure    und 14 Teile       (i/20        Mol)    des     Natriumsalzes    der     3-Amino-4'-          oxy-1,1'-azobenzol-5'-carbonsäure    in 300 Teilen  Wasser, :

  der man 10 Teile     Calciumearbona,t     beifügte, rasch zugegeben. Man rührt bei  Raumtemperatur während 48 Stunden und  trennt den Farbstoff als     Natriumsalz    ab.  



  Der so erhaltene Farbstoff stellt ein blau  schwarzes Pulver dar, das sich in Wasser mit  leuchtend blauer und in     konz.    Schwefelsäure  mit     gelbgrüner    Farbe löst. Der Farbstoff  eignet sich im     besonderen    für den Chrom  druck auf Baumwolle; man erhält ein leuch  tendes Grasgrün von     hervorragenden        Nass-          echtheiten    und vorzüglicher Lichtechtheit.



  The present invention relates to a process for the production of a water-soluble and licensing azophthalocyanine dye, which is characterized in that it has 1 mol 11,

  Copper phthalocyanine containing 5% bromine - 4,4 ', 4 ", 4"' - tetrasulfo.- ehlorid, as can be obtained by the action of chlorosulfonic acid on brominated copper phtha.locyanine - 4,41,4 ", 4" '- tetrasulfo - acid, with 1 mol of 3-amino-4'-oxy-1,

  1'-azo-benzene-5'-carboxylic acid and 2 mol. 1,3-Dioxy-benzene-4-carboxylic acid in the presence of a mineral acid-binding substance.



  In addition, the statements mentioned in the main patent apply with regard to the preferred implementation of the process according to the invention.



  The example below explains the new procedure. The parts indicated are parts by weight.



       Example 64 parts (1/20 mol) of brominated copper phthalocyanine 4,4 ', 4 ", 4"' - tetrasulfoehlorid, obtained by the action of chlorosulfonic acid on brominated copper phthalocyanine 4,4 ', 4 ", 4 "'- sulfonic acid (according to analysis contains 11.5% bromine),

          are discharged onto ice, the suctioned off reaction product is mixed with 300 parts of crushed ice and a solution containing 19.8 parts (1/10 mol) of the disodium salt of 1,3-dioxybenzene-4-carboxylic acid and 14 parts (i / 20 mol) of the sodium salt of 3-amino-4'-oxy-1,1'-azobenzene-5'-carboxylic acid in 300 parts of water:

  to which 10 parts of calcium carbonate were added, quickly added. The mixture is stirred at room temperature for 48 hours and the dye is separated off as the sodium salt.



  The dye obtained in this way is a blue-black powder, which is bright blue in water and in conc. Sulfuric acid dissolves with a yellow-green color. The dye is particularly suitable for chrome printing on cotton; a brilliant grass green with excellent wet fastness and excellent light fastness is obtained.

Claims (1)

PATENTANSPRUCH Verfahren zur Herstellung eines wasser löslichen und beizenziehenden Azophthalo- cyaninfarbstoffes, dadurch gekennzeichnet, dass man 1 Mol 11,5 % Brom enthaltendes Kupferphthalocyanin - 4, 4',!4", 4"' - tetrasLLlfo - chlorid, wie es erhältlich ist .durch Einwir kung von. PATENT CLAIM Process for the production of a water-soluble and associated azophthalocyanine dye, characterized in that 1 mol of 11.5% bromine-containing copper phthalocyanine - 4, 4 ',! 4 ", 4"' - tetrasLLlfo - chloride, as it is available. by the action of. ChlorsLLlfonsäure auf bromierte Kupferphthaloeyanin - 4,41,4", 4"' - tetrasulfo - säure, mit 1 Mol 3-Amino-4'-oxy-1,1'-azo- 'aen7ol-5'-carbonsäure und 2 Mol 1,3-Dioxy- benzol.-4-carbonsä:ure in Gegenwart, einer Mi neralsäure bindenden Substanz zur Um setzung bringt. Chlorosulfonic acid on brominated copper phthaloeyanine - 4,41,4 ", 4" '- tetrasulfonic acid, with 1 mole of 3-amino-4'-oxy-1,1'-azo-' aen7ol-5'-carboxylic acid and 2 moles of 1 , 3-Dioxybenzene-4-carboxylic acid: acid in the presence of a mineral acid-binding substance. Der so erhaltene Farbstoff stellt ein blau- sehwarzes Pulver dar, das sich in Wasser mit leuchtend blauer und in konz. Schwefelsäure mit gelbgrüner Farbe löst. Der Farbstoff eignet sieh im besonderen für den Chrom- druck auf Baumwolle; man erhält ein leuch tendes Grasgrün von hervorragenden Nass- eehtheiten und vorzüglicher Lichtechtheit. The dye obtained in this way is a bluish-black powder that turns bright blue in water and in conc. Sulfuric acid dissolves with a yellow-green color. The dye is particularly suitable for chrome printing on cotton; the result is a shining grass green with excellent wetness properties and excellent lightfastness.
CH314551D 1953-01-14 1953-01-15 Process for the preparation of a water-soluble and licensing azophthalocyanine dye CH314551A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH311212T 1953-01-14
CH314551T 1953-01-15

Publications (1)

Publication Number Publication Date
CH314551A true CH314551A (en) 1956-06-15

Family

ID=25735847

Family Applications (1)

Application Number Title Priority Date Filing Date
CH314551D CH314551A (en) 1953-01-14 1953-01-15 Process for the preparation of a water-soluble and licensing azophthalocyanine dye

Country Status (1)

Country Link
CH (1) CH314551A (en)

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