CH309797A - Process for the preparation of the 3'-oxy-4'-carboxyphenyl ester of a metal-containing phthalocyanine tetrasulfonic acid. - Google Patents

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

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Publication number
CH309797A
CH309797A CH309797DA CH309797A CH 309797 A CH309797 A CH 309797A CH 309797D A CH309797D A CH 309797DA CH 309797 A CH309797 A CH 309797A
Authority
CH
Switzerland
Prior art keywords
acid
oxy
cotton
blue
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 CH309797A publication Critical patent/CH309797A/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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)

Description

  

  <B>Verfahren zur Herstellung des</B>     3'-Oxy-4'-carboxyphenylesters   <B>einer metallhaltigen</B>       Phthaloeyanintetrasulfonsäure.            Gegenstand    der vorliegenden Erfindung  ist ein Verfahren zur Herstellung des     3'-Oxy-          4'-earboxyphenylesters    einer     Kupferphthalo-          eyanintetrasulfonsäure,    welches     dadurch    ge  kennzeichnet ist, dass man     1.        Mol        Kupfer-          phthalocyanin-4,4',4",4?"-tetrasulfochlorid    mit  4 Molen     1,

  3-Dioxybenzol-4-earbonsäure    in  Gegenwart einer Mineralsäure neutralisieren  den Substanz zur     Umsetzung    bringt.  



  Das zu verwendende     Kupferphthalocyanin-          tetrasulfochlorid    kann durch Einwirkung von       Chlorsulfonsäure    auf     Kupferphthalocyanin-          4,4',4",4"'-tetrasulfonsäure    erhalten werden.  



  Im nachfolgenden Beispiel bedeuten die       Teile    Gewichtsteile.    <I>Beispiel:</I>  96,9 Teile     (1/1o        Mol)        Kupferphthaloeyanin-          4,4',4",4'-t.etrasulfochlorid,    erhalten durch  Einwirkung von     Chlorsulfonsäure    auf     Kupfer-          phthaloeyanin-4,4',4",4"'-tetrasulfonsäure,    wer  den mit 300 Teilen zerkleinertem     Eis    gut     ver-          rnischt    und unter Rühren eine Lösung von  65 Teilen     (411o        Mol)        1,

  3-Dioxybenzol-4-carbon-          säure    mit 34 Teilen     Natriumhydroxyd    (100 %)  in 300 Teilen Wasser zugefügt. Man lässt das       Reaktionsgemisch    während 8 Stunden unter  Eiskühlung und dann während weiteren 12  bis 15 Stunden bei 20-25  C rühren, bis völ  lige     Lösung    eingetreten ist. Die so erhaltene  dunkelblaue, klare Lösung     wird    mit Salzsäure  angesäuert., die ausgefallene     Farbstoffsäure          abgetrenntund    in das     Natriumsalz    übergeführt.

      Das in     guter    Ausbeute erhaltene Natrium  salz des     3'-Oxy-4'-carboxyphenylesters    der       Kupferphthalocyanin-4,    4', 4",     4"'-tetra6uIfon-          säure    stellt ein blauviolettes Pulver dar, das  sich in Wasser mit tiefblauer und in     konz.     Schwefelsäure mit leuchtend grüner     Farbe     löst. Der neue Farbstoff eignet sich zum Fär  ben von Baumwolle, Viskose und Wolle. Es  werden     grünstichige    Blautöne von mässigen       Nassechtheiten    und guter Lichtechtheit erhal  ten.

   Auf     vorchromierter    Baumwolle werden  bedeutend kräftigere Farbtöne erhalten, und  es ist eine deutliche Verbesserung der     Nass-          und    Lichtechtheit festzustellen. Im     besondern     eignet sich der Farbstoff im Chromdruck auf  Baumwolle, wobei kräftige Blautöne von sehr  guten     Nassechtheiten    und vorzüglicher     Lieht-          echtheit    erhalten werden.  



  Auf     anodisch    oxydiertes Aluminium ge  färbt, ergibt der Farbstoff ein     blaustichiges     Grün.



  <B> Process for producing the </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 the 3'-oxy-4'-earboxyphenyl ester of a copper phthalo- eyanin tetrasulfonic acid, which is characterized in that 1. mole of copper phthalocyanine-4,4 ', 4 ", 4?" -tetrasulfochloride with 4 moles 1,

  3-Dioxybenzene-4-carboxylic acid in the presence of a mineral acid neutralizes the substance and reacts.



  The copper phthalocyanine tetrasulfochloride to be used can be obtained by the action of chlorosulfonic acid on copper phthalocyanine 4,4 ', 4 ", 4"' - tetrasulfonic acid.



  In the following example, the parts are parts by weight. <I> Example: </I> 96.9 parts (1 / 1o mol) copper phthaloeyanine 4,4 ', 4 ", 4'-t.etrasulfochlorid, obtained by the action of chlorosulfonic acid on copper phthaloeyanine 4,4' , 4 ", 4" '- tetrasulfonic acid, who mix well with 300 parts of crushed ice and stir a solution of 65 parts (411o mol) 1,

  3-Dioxybenzene-4-carboxylic acid with 34 parts of sodium hydroxide (100%) in 300 parts of water was added. The reaction mixture is allowed to stir for 8 hours with ice cooling and then for a further 12 to 15 hours at 20-25 ° C. until complete solution has occurred. The dark blue, clear solution thus obtained is acidified with hydrochloric acid, the precipitated dye acid is separated off and converted into the sodium salt.

      The sodium salt of the 3'-oxy-4'-carboxyphenyl ester of copper phthalocyanine-4, 4 ', 4 ", 4"' - tetra6uIfonic acid, obtained in good yield, is a blue-violet powder that dissolves in water with deep blue and conc . Sulfuric acid with a bright green color dissolves. The new dye is suitable for dyeing cotton, viscose and wool. Greenish blue tones with moderate wet fastness and good light fastness are obtained.

   Significantly stronger colors are obtained on pre-chromed cotton, and there is a clear improvement in wet and light fastness. The dye is particularly suitable for chrome printing on cotton, with strong blue tones with very good wet fastness properties and excellent light fastness.



  When colored on anodically oxidized aluminum, the dye gives a bluish green.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung des 3'-Oxy-4'- carboxyphenylesters einer Kupferphthalo- cyanintetrasulfansäure, dadurch gekennzeich net, dass man. PATENT CLAIM: Process for the preparation of the 3'-oxy-4'-carboxyphenyl ester of a copper phthalocyanine tetrasulfanic acid, characterized in that one. 1 Mol Kupferphthalocyanin- 4,4',4",4"'-tetrasulfochlorid mit 4 Molen 1,3- Dioxybenzol-4-carbonsäure in Gegenwart einer Mineralsäure neutralisierenden Substanz zur Umsetzung bringt. Der neue Farbstoff stellt in Form seines Natriumsalzes ein blauviolettes Pulver dar, das sich in Wasser mit tiefblauer und in konz. Schwefelsäure mit leuchtend grüner Farbe löst. Der neue Farbstoff eignet sich zum Fär ben von Baumwolle, Viskose und Wolle. 1 mole of copper phthalocyanine 4,4 ', 4 ", 4"' - tetrasulfochloride with 4 moles of 1,3-dioxybenzene-4-carboxylic acid in the presence of a mineral acid-neutralizing substance to react. In the form of its sodium salt, the new dye is a blue-violet powder that dissolves in water with deep blue and in conc. Sulfuric acid with a bright green color dissolves. The new dye is suitable for dyeing cotton, viscose and wool. Es werden grünstichige Blautöne von mässigen Nassechtheiten und guter Lichtechtheit erhal ten. Auf vorchromierter Baumwolle werden bedeutend kräftigere Farbtöne erhalten, und es ist eine deutliche Verbesserung der Na.ss- und Lichtechtheit. festzustellen. Im besondern eignet sich der Farbstoff im Chromdruck auf Baumwolle, wobei kräftige Blautöne von sehr guten Nassechtheiten und vorzüglicher Licht- eehtheit erhalten werden. Greenish blue tones with moderate wet fastness properties and good light fastness are obtained. Significantly stronger colors are obtained on pre-chrome-plated cotton, and there is a significant improvement in the water and light fastness. ascertain. The dye is particularly suitable for chrome printing on cotton, with strong blue tones with very good wet fastness properties and excellent light fastness.
CH309797D 1952-01-08 1952-01-08 Process for the preparation of the 3'-oxy-4'-carboxyphenyl ester of a metal-containing phthalocyanine tetrasulfonic acid. CH309797A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH309797T 1952-01-08
CH306387T 1957-03-27

Publications (1)

Publication Number Publication Date
CH309797A true CH309797A (en) 1955-09-15

Family

ID=25735140

Family Applications (1)

Application Number Title Priority Date Filing Date
CH309797D CH309797A (en) 1952-01-08 1952-01-08 Process for the preparation of the 3'-oxy-4'-carboxyphenyl ester of a metal-containing phthalocyanine tetrasulfonic acid.

Country Status (1)

Country Link
CH (1) CH309797A (en)

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