CH215404A - Process for the preparation of a phthalocyanine series dye. - Google Patents

Process for the preparation of a phthalocyanine series dye.

Info

Publication number
CH215404A
CH215404A CH215404DA CH215404A CH 215404 A CH215404 A CH 215404A CH 215404D A CH215404D A CH 215404DA CH 215404 A CH215404 A CH 215404A
Authority
CH
Switzerland
Prior art keywords
dye
preparation
phthalocyanine series
series dye
acid
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 CH215404A publication Critical patent/CH215404A/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
    • C09B47/06—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
    • C09B47/062—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide having alkyl radicals linked directly to the Pc skeleton; having carboxylic groups directly linked to the skeleton, e.g. phenyl

Landscapes

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

Description

  

  Verfahren zur Herstellung eines     Farbstoffes    der     Phthaloeyaninreihe.       Es wurde gefunden, dass man neue       Phthalocyanine    durch Erhitzen solcher       Phthalsäuren,    welche in 4- und     5-,Stellung          durch        Arylreste        substituiert        sind,    mit Kup  fersalzen und Ammoniak abgebenden     Mitteln     wie Harnstoff oder     amidosulfonsauren    Sal  zen, zum     Beispiel    dem     Ammoniumsalz    her  stellen kann.

       Vorzugsweise    wird bei Gegen  wart geringer Mengen von die     Reaktion    för-         .dernden    Stoffen     wie        Phosphaten,        Yanadina-          ten    und     Molybdaten    ;gearbeitet. Die neuen       Phthalocyanine        stellen    grüne     Pigmente    dar,  die als solche als     Pigmentfarbstoffe    verwandt  werden können.

   Durch     'S.ulfieren        erhält    man       wasserlösliche        Sulfosäuren.     



  Die als     Ausgangsmaterial    benutzten     4;5-          Diarylphthals5,uren    können auf dem Wege  der     "Diensynthese"    leicht nach folgendem  Schema erhalten werden:  
EMI0001.0034     
    Man addiert zu     diesem        Zweck    ein     2,3-Di-          arylbutadien    (1) an     Maleineäureanhydrid       (2) und unterwirft     das    dabei erhaltene  4,5 -     Diaryl    -     tetrahydrophthalsäureanhydrid         (3) der     Dehydrierung,

          beispielsweise        durch          Erhitzen.        mit    Schwefel, wobei die     4;5-Di-          arylphthalsäuren    erhalten werden.  



  Gegenstand des vorliegenden     Patentes    ist  nun die Herstellung eines speziellen Farb  stoffes der     Phtha.locyaninreihe    durch Er  hitzen von     4,5-Diphenylphthalsäure    mit       Harnstoff    und einem Kupfersalz.

   Es emp  fiehlt sich, in Gegenwart eines     Katalysators          wie        Ammoniummolybdat    zu     arbeiten.    Der  erhältliche neue Farbstoff stellt ein grünes  bronzierendes Pulver dar, welches in allen  organischen     Lösungsmitteln    praktisch unlös  lich und in     konzentrierter    Schwefelsäure     Iös-          lich    ist. Er kann als Pigmentfarbstoff be  nutzt werden.  



  <I>Beispiel:</I>  Man erhitzt ein inniges Gemisch aus  100 Gewichtsteilen     4,5-Diphenylphthalsäure          (aus        Acetonnitril    farblose Prismen vom       Schmelzpunkt    221   unter     Schäumen),    300  Gewichtsteilen Harnstoff, 20 Gewichtsteilen  Kupferchlorid und 2     Gewiehtstei,len        Ammo-          niummolybdat    bis zur     Beendigung    der     Farb-          atoffbildung    auf     230-250'.    Danach kocht,

    man die Schmelze mit verdünnter Natron  lauge und verdünnter     .Salzsäure    aus     und    er  hält das     Oktophenyl-Kupferphthalocya,nin       als grünes     bronzierendes    Pulver.     Das    Pro  dukt     ist    in allen     organischen        Usungsmit-          teln    nahezu unlöslich.

   In konzentrierter       Schwefelsäure    löst es sich mit braunviolet  ter Farbe.     Beim        Eingiessen    dieser     Lösung    in       Wasser    erhält man     leuchtend    grüne Flocken.



  Process for the preparation of a dye of the phthaloeyanine series. It has been found that new phthalocyanines can be produced by heating phthalic acids which are substituted in the 4- and 5- positions by aryl radicals with copper salts and ammonia-releasing agents such as urea or amidosulfonic acid salts, for example the ammonium salt.

       It is preferable to work in the presence of small amounts of substances that promote the reaction, such as phosphates, yanadinates and molybdates. The new phthalocyanines are green pigments that can be used as such as pigment dyes.

   Water-soluble sulfonic acids are obtained by sulfating.



  The 4,5-diarylphthalic acids used as starting material can easily be obtained by the "diene synthesis" according to the following scheme:
EMI0001.0034
    For this purpose, a 2,3-diarylbutadiene (1) is added to maleic anhydride (2) and the 4,5-diaryl-tetrahydrophthalic anhydride (3) obtained is subjected to dehydrogenation,

          for example by heating. with sulfur, the 4; 5-diarylphthalic acids being obtained.



  The subject of the present patent is the production of a special dye of the Phtha.locyanin series by heating 4,5-diphenylphthalic acid with urea and a copper salt.

   It is recommended to work in the presence of a catalyst such as ammonium molybdate. The new dye available is a green, bronzing powder, which is practically insoluble in all organic solvents and soluble in concentrated sulfuric acid. It can be used as a pigment.



  <I> Example: </I> An intimate mixture of 100 parts by weight of 4,5-diphenylphthalic acid (made of acetonitrile colorless prisms with a melting point of 221 with foaming), 300 parts by weight of urea, 20 parts by weight of copper chloride and 2 parts by weight of ammonium molybdate is heated to end the dye formation to 230-250 '. After that cooks

    you remove the melt with dilute sodium hydroxide solution and dilute hydrochloric acid and it keeps the octophenyl copper phthalocyanine as a green, bronzing powder. The product is almost insoluble in all organic solvents.

   It dissolves in concentrated sulfuric acid with a brown-violet color. When this solution is poured into water, bright green flakes are obtained.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Farb stoffes der Phthalocyaninreihe, dadurch ge kennzeichnet, dass man 4,5-Diphenylphthal- säure mit Harnstoff und einem Kupfersalz umsetzt. Der Farbstoff stellt ein grünes bronzie rendes Pulver dar, welches in allen organi schen Lösungsmitteln praktisch unlöslich und in konzentrierter Schwefelsäure löslich ist. PATENT CLAIM: Process for the production of a dye of the phthalocyanine series, characterized in that 4,5-diphenylphthalic acid is reacted with urea and a copper salt. The dye is a green bronzing powder, which is practically insoluble in all organic solvents and soluble in concentrated sulfuric acid. Er kann als Pigmentfarbstoff benutzt werden. UNTERANSPRUCH: '\'erfa.hren nach Patentanspruch, dadurch gekennzeichnet, dass in Gegenwart von Ammoniummolybdat als Katalysator ge arbeitet wird. It can be used as a pigment. SUBCLAIM: '\' learn according to claim, characterized in that the catalyst is used in the presence of ammonium molybdate.
CH215404D 1938-08-09 1939-07-21 Process for the preparation of a phthalocyanine series dye. CH215404A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE215404X 1938-08-09

Publications (1)

Publication Number Publication Date
CH215404A true CH215404A (en) 1941-06-30

Family

ID=5823785

Family Applications (1)

Application Number Title Priority Date Filing Date
CH215404D CH215404A (en) 1938-08-09 1939-07-21 Process for the preparation of a phthalocyanine series dye.

Country Status (1)

Country Link
CH (1) CH215404A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2681344A (en) * 1950-01-12 1954-06-15 Ici Ltd Coloring matters of the tetra-aza porphin series

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2681344A (en) * 1950-01-12 1954-06-15 Ici Ltd Coloring matters of the tetra-aza porphin series

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