CH309799A - Process for the preparation of a 3'-oxy-4'-carboxyphenyl ester of a metal-containing phthalocyanine tetrasulfonic acid. - Google Patents

Process for the preparation of a 3'-oxy-4'-carboxyphenyl ester of a metal-containing phthalocyanine tetrasulfonic acid.

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Publication number
CH309799A
CH309799A CH309799DA CH309799A CH 309799 A CH309799 A CH 309799A CH 309799D A CH309799D A CH 309799DA CH 309799 A CH309799 A CH 309799A
Authority
CH
Switzerland
Prior art keywords
acid
bromine
parts
oxy
preparation
Prior art date
Application number
Other languages
German (de)
Inventor
Ag Durand Huguenin
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 CH309799A publication Critical patent/CH309799A/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
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Developing Agents For Electrophotography (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Description

  

  <B>Zusatzpatent</B>     zum    Hauptpatent Nr. 306387.    <B>Verfahren zur Herstellung eines</B>     3'-Oxy-4'-carboxyphenylesters   <B>einer metallhaltigen</B>       Phthaloeyanintetrasulfonsäure.       Gegenstand der vorliegenden Erfindung ist  ein Verfahren zur     Herstellung    eines     3'-0xy-          4'    -     carboxyphenylesters    einer bromhaltigen       Kupferphthalocyanintetrasulfonsäure,    welches  dadurch gekennzeichnet ist, dass man 1     Mol     14,5 0/0 Brom enthaltendes     Kupferphthalo-          cyanin    - 3,3',3",

  3"' -     tetrasulfochlorid,    wie es  erhältlich ist durch Einwirkung von 92 Teilen  Brom auf 100 Teile     Kupferphthaloeyanin-          3,3',3",3"'-tetrasulfonsäure    und anschliessende  Einwirkung von     Chiorsulfonsäure,    mit 4 Mo  len     1,3-Dioxybenzol-4-carbonsäure    in Gegen  wart einer Mineralsäure 'neutralisierenden  Substanz zur Umsetzung bringt.  



  Im nachfolgenden Beispiel bedeuten die  Teile     Gewichtsteile.     



  <I>Beispiel:</I>  64,2 Teile     (1/2o        Mol)        bromiertes        Kupfer-          phthalocya.nin-3,3',3",31"-tetrasulfochlorid    (er  halten durch Einwirkung von 92 Teilen Brom  auf 100 Teile     Kupferphthalocyanin-3,3',3",3"'-          tetrasulfonsäure    und anschliessende Einwir  kung von     Chlorsulfonsäure,    wobei das so erhal       tenebromierteKupferphthalocyanin-3,3',3",3"'-          tetrasttlfochlorid        14,5%        Brom        enthält)

          wer-          den    auf Eis ausgeladen, das     abgesogene    Reak  tionsprodukt mit 200 Teilen zerkleinertem Eis  vermischt und unter Rühren eine Lösung von  32,5 Teilen (4/2o M01)     1.,3-Dioxybenzol-4-          carbonsäure    und 17 Teilen     Natriumhydroxyd            (100        %)        in        250        Teilen        Wasser        zugefügt.        Nach     mehrstündigem Rühren bei 10-15  C tritt  völlige Lösung ein.

   Nach dem     Ansäuern    mit       Salzsäure    wird die ausgefallene Farbstoff  säure abgetrennt und in das     Natriumsalz    über  geführt.  



  Der neue Farbstoff stellt ein graublaues  Pulver dar, das sich in Wasser mit blauer  und in     konz.    Schwefelsäure mit olivgrüner  Farbe löst. und., auf     vorchromierter    Baumwolle  gefärbt, blaustichig grüne Farbtöne von sehr  guter Nass- und Lichtechtheit gibt. Im Chrom  druck auf Baumwolle werden reine     grün-          stichige    Blautöne von sehr guten     Echtheiten     erhalten.



  <B> Additional patent </B> to main patent no. 306387. <B> Process for the production of a </B> 3'-oxy-4'-carboxyphenyl ester <B> of a metal-containing </B> phthaloeyanine tetrasulfonic acid. The present invention relates to a process for the preparation of a 3'-oxy-4'-carboxyphenyl ester of a bromine-containing copper phthalocyanine tetrasulfonic acid, which is characterized in that 1 mol of 14.5% bromine-containing copper phthalocyanine-3,3 ', 3 ",

  3 "'- tetrasulfochlorid, as it is obtainable by the action of 92 parts of bromine to 100 parts of copper phthaloeyanine 3,3', 3", 3 "'- tetrasulfonic acid and subsequent action of chlorosulfonic acid, with 4 Mo len 1,3-dioxybenzene 4-carboxylic acid in the presence of a mineral acid 'neutralizing substance to implement.



  In the following example, the parts are parts by weight.



  <I> Example: </I> 64.2 parts (1 / 2o mol) of brominated copper phthalocya.nin-3,3 ', 3 ", 31" -tetrasulfochloride (obtained by the action of 92 parts of bromine per 100 parts Copper phthalocyanine 3,3 ', 3 ", 3"' - tetrasulphonic acid and subsequent exposure to chlorosulphonic acid, the so obtained copper phthalocyanine 3,3 ', 3 ", 3"' - tetrasttlfochlorid containing 14.5% bromine)

          are unloaded on ice, the sucked off reac tion product mixed with 200 parts of crushed ice and a solution of 32.5 parts (4 / 2o M01) 1., 3-dioxybenzene-4-carboxylic acid and 17 parts of sodium hydroxide (100% ) added in 250 parts of water. After several hours of stirring at 10-15 ° C., complete solution occurs.

   After acidification with hydrochloric acid, the precipitated dye acid is separated off and converted into the sodium salt.



  The new dye is a gray-blue powder that turns blue in water and in conc. Dissolves sulfuric acid with an olive green color. and., dyed on pre-chromed cotton, gives bluish green shades of very good wet and light fastness. In the chrome print on cotton, pure greenish blue tones with very good fastness properties are obtained.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines 3'-Oxy-4'- carboxyphenylesters einer bromhaltigen Kup- ferphthaloeyanin- 3,3',3",3"' - tetrasulfonsäure, dadurch gekennzeichnet, dass man 1 Mol 14,5 % Brom enthaltendes Kupferphthalo- cyanin - 3, 3', 3", 3"' - tetrasulfochlorid, PATENT CLAIM: Process for the preparation of a 3'-oxy-4'-carboxyphenyl ester of a bromine-containing copper phthaloeyanine 3,3 ', 3 ", 3"' - tetrasulfonic acid, characterized in that 1 mol of 14.5% bromine-containing copper phthalo- cyanine - 3, 3 ', 3 ", 3"' - tetrasulfochlorid, wie es erhältlich ist durch Einwirkung von 92 Teilen Brom auf 100 Teile Kupferphthalocyanin- 3,3',3",3"'-tetrasulfonsäure und anschliessende Einwirkung von Chlorsulfonsäure, mit 4 Molen 1,3-Dioxybenzol-4-carbonsäure in Gegenwart einer Mineralsäure neutralisierenden Substanz zur Umsetzung bringt. Der neue Farbstoff stellt ein graublaues Pulver dar, das sich in Wasser mit blauer und in konz. Schwefelsäure mit olivgrüner Farbe löst und, auf vorchromierter Baumwolle gefärbt, blaustichig grüne Farbtöne von sehr guter Nass- und Lichtechtheit gibt. as obtainable by the action of 92 parts of bromine to 100 parts of copper phthalocyanine-3,3 ', 3 ", 3"' - tetrasulfonic acid and subsequent action of chlorosulfonic acid with 4 moles of 1,3-dioxybenzene-4-carboxylic acid in the presence of a mineral acid brings neutralizing substance to implementation. The new dye is a gray-blue powder that turns blue in water and in conc. Sulfuric acid dissolves with an olive green color and, when dyed on pre-chromed cotton, gives bluish green shades of very good wet and light fastness. Im Chrom druck auf Baumwolle werden reine grün- stichige Blautöne von sehr guten Echtheiten erhalten. In the chrome print on cotton, pure greenish blue tones with very good fastness properties are obtained.
CH309799D 1952-01-08 1952-01-08 Process for the preparation of a 3'-oxy-4'-carboxyphenyl ester of a metal-containing phthalocyanine tetrasulfonic acid. CH309799A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH309799T 1952-01-08
CH306387T 1957-03-27

Publications (1)

Publication Number Publication Date
CH309799A true CH309799A (en) 1955-09-15

Family

ID=25735142

Family Applications (1)

Application Number Title Priority Date Filing Date
CH309799D CH309799A (en) 1952-01-08 1952-01-08 Process for the preparation of a 3'-oxy-4'-carboxyphenyl ester of a metal-containing phthalocyanine tetrasulfonic acid.

Country Status (1)

Country Link
CH (1) CH309799A (en)

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