CH200544A - Process for the preparation of a chromium compound of the phthalein dye which is soluble in organic solvents containing hydroxyl groups from 2- [4'-dimethylamino-2'-oxybenzoyl] -benzoic acid and B-resorcylic acid. - Google Patents

Process for the preparation of a chromium compound of the phthalein dye which is soluble in organic solvents containing hydroxyl groups from 2- [4'-dimethylamino-2'-oxybenzoyl] -benzoic acid and B-resorcylic acid.

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Publication number
CH200544A
CH200544A CH200544DA CH200544A CH 200544 A CH200544 A CH 200544A CH 200544D A CH200544D A CH 200544DA CH 200544 A CH200544 A CH 200544A
Authority
CH
Switzerland
Prior art keywords
acid
oxybenzoyl
chromium compound
organic solvents
dimethylamino
Prior art date
Application number
Other languages
German (de)
Inventor
A-G J R Geigy
Original Assignee
Geigy Ag J R
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 Geigy Ag J R filed Critical Geigy Ag J R
Publication of CH200544A publication Critical patent/CH200544A/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
    • 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
    • C09B11/10—Amino derivatives of triarylmethanes
    • C09B11/24—Phthaleins containing amino groups ; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes
    • C09B11/245—Phthaleins having both OH and amino substituent(s) on aryl ring
    • 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
    • C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
    • C09B5/02—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic ring being only condensed in peri position
    • C09B5/20—Flavanthrones

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Zusatzpatent zum Hauptpatent     Nr.   <B>197284.</B>    Verfahren zur Herstellung einer in     hydroxylgruppenhaltigen    organischen  Lösungsmitteln löslichen Chromverbindung     des        Phthaleinfarbstoffes    aus       2-[41-Dimethylamino-2'-oxybenzoyl]-benzoosä,

  ure    und     P-Besorcylsäure.       Gegenstand dieses Patentes ist ein Ver  fahren zur Darstellung einer in     hydroxyl-          gruppenhaltigen    organischen Lösungsmitteln  löslichen     Chromverbinclung    des     Phthalein-          farbstoffes    aus     2-[4'-Dimethylamino-2-oxy-          benzoyl]-benzoesäure    und     ss-Resorcylsäure.     Behandelt man, zweckmässig unter Erhitzen,  die zum Beispiel nach üblichem Verfahren  dargestellte,

   in Wasser und organischen Lö  sungsmitteln unlösliche braune Chromver  bindung des     Phthaleinfarbstoffes    aus     2-[4'-          Dimethylami-no   <B>-</B> 2-     oxybenzoyl]   <B>-</B>     benzoesäure     und     ss-Resoreylsäure    mit Salzsäure oder Ver  bindungen, die Salzsäure abspalten, in Gegen  wart von organischen     Verdünnungsmitteln,     so erhält man nach dem Verjagen des Ver  dünnungsmittels ein rotbraunes, grünglän  zendes Pulver, das in niederen Alkoholen  sehr gut löslich ist und dessen     Laekfärbun-          gen    sich durch sehr gute Lichtechtheit aus  zeichnen.

      <I>Beispiel<B>1:</B></I>  <B>123</B> Teile der unlöslichen     Chromverbiu-          dung    des     beizenfärbenden        Phthaleinfarbstof-          ès,    der aus     2-[4'-Dimethylamino-2'-oxy-          benzoyl]-benzoesä,ure    und     ss-Resoreylsäure    in  Schwefelsäure bei<B>55</B> bis<B>60' C</B> in einigen  Stunden erhalten und in     üblic'her    Weise     ehro-          miert    wird,

   werden in<B>500</B> Teilen Alkohol bei  <B>60</B> bis<B>78 '</B>     C    unter Rühren innert<B>1</B> Stunde  mit 40 Teilen     Miger    Salzsäure tropfen  weise versetzt, wobei eine rotbraun gefärbte  Lösung entsteht. Durch     Abdestillieren    des  Alkohols und Trocknen im Vakuum werden  <B>136</B> Teile eines rotbraunen, grünglänzenden  Pulvers erhalten, das sieh in niederen Alko  holen und auch in Wasser sehr leicht mit  gelblich roter Farbe löst. Die Löslichkeit in       Äthylalkohol    übersteigt<B>10 % ;</B> die Färbungen  von     Zelluloseesterlacken    zeichnen sieh durch  gute Lichtechtheit aus.

        <I>Beispiel 2:</I>  <B>5</B> Teile der in Beispiel<B>1</B> als Ausgangs  material verwendeten Chromverbindung wer  den in 40 Teilen Alkohol     angeschUmmt    und  mit     3,5    Teilen     Aluminiumehlorid    bei<B>78' C</B>  <B>90</B> Minuten gerührt; man erhält eine klare,  rotbraun gefärbte Lösung. Nach dem Ver  dunsten des Alkohols bleibt ein in niederen  Alkoholen     usw.    sehr gut lösliches rotbraunes,  grünglänzendes Pulver zurück, das in     Zellu-          loseesterlacken    gute Lichtechtheit zeigt.  



  Ähnliche Verbindungen erhält man durch  Verwendung von Eisen- oder     Zinnehlorid    an  Stelle von     Aluminiumehlorid.  



  Additional patent to main patent no. <B> 197284. </B> Process for the production of a chromium compound of the phthalein dye which is soluble in organic solvents containing hydroxyl groups from 2- [41-dimethylamino-2'-oxybenzoyl] -benzoosä,

  ure and P-besorcylic acid. The subject of this patent is a process for the preparation of a chromium compound of the phthalein dye from 2- [4'-dimethylamino-2-oxybenzoyl] benzoic acid and β-resorcylic acid which is soluble in organic solvents containing hydroxyl groups. If one treats, expediently with heating, the, for example, represented by the usual procedure,

   Brown chromium compound of the phthalein dye made from 2- [4'-dimethylamino-no <B> - </B> 2- oxybenzoyl] <B> - </B> benzoic acid and ß-resoreyl acid with hydrochloric acid, which is insoluble in water and organic solvents Compounds that split off hydrochloric acid in the presence of organic diluents result in a red-brown, green-glossy powder which is very soluble in lower alcohols and whose laek colorations are characterized by very good lightfastness after the diluent has been chased away .

      <I> Example<B>1:</B> </I> <B> 123 </B> Parts of the insoluble chromium compound of the stain-coloring phthalein dye, which consists of 2- [4'-dimethylamino-2'- oxybenzoyl] -benzoic acid and ß-resoreyl acid in sulfuric acid at <B> 55 </B> to <B> 60 'C </B> is obtained in a few hours and horned in the usual way,

   are added dropwise in <B> 500 </B> parts of alcohol at <B> 60 </B> to <B> 78 '</B> C with stirring within <B> 1 </B> hour with 40 parts of Miger hydrochloric acid wise offset, whereby a red-brown colored solution is formed. By distilling off the alcohol and drying in vacuo, <B> 136 </B> parts of a red-brown, green-glossy powder are obtained, which can be found in lower alcohol and also very easily dissolves in water with a yellowish-red color. The solubility in ethyl alcohol exceeds <B> 10%; </B> the colorations of cellulose ester lacquers are characterized by good lightfastness.

        <I> Example 2: </I> <B> 5 </B> parts of the chromium compound used as starting material in example <B> 1 </B> are encased in 40 parts of alcohol and mixed with 3.5 parts of aluminum chloride Stirred for <B> 78 'C </B> <B> 90 </B> minutes; a clear, red-brown colored solution is obtained. After the alcohol has evaporated, a red-brown, green, glossy powder which is very soluble in lower alcohols etc. remains, which shows good lightfastness in cellulose ester lacquers.



  Similar compounds are obtained by using iron or tin chloride instead of aluminum chloride.

Claims (1)

<B>PATENTANSPRUCH:</B> Verfahren zur Darstellung einer in hy- droxylgruppenhaltigen organischen Lösungs# mitteln löslichen Chromverbindung des Phthaleinfarbstoffes aus 2-[4-Dimethyl- amino-2'-oxybenzoyl]-benzoesäure und O-Re- sorcylsäure, dadurch gekennzeichnet, PATENT CLAIM: Process for the preparation of a chromium compound of the phthalein dye, which is soluble in organic solvents containing hydroxyl groups, from 2- [4-dimethylamino-2'-oxybenzoyl] benzoic acid and O-resorbic acid, thereby marked, dass man die in Wasser und organischen Lösungs mitteln unlösliche braune Chromverbindung des Phthaleinfarbstoffes aus 2-[4'-Dimethyl- amino-2'-oxybenzoyl]-benzoesäwure und fl-Re- sorcylsäure in Gegenwart von organischen Verdünnungsmitteln mit Salzsäure oder Salzsäure abspaltenden Verbindungen be handelt. UNTERANSPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man die Behandlung un ter Erhitzen vornimmt. that the brown chromium compound of the phthalein dye, which is insoluble in water and organic solvents, is obtained from 2- [4'-dimethyl-amino-2'-oxybenzoyl] -benzoic acid and fl-sorcylic acid in the presence of organic diluents with hydrochloric acid or hydrochloric acid-cleaving compounds acts. SUBClaim: Method according to claim, characterized in that the treatment is carried out under heating.
CH200544D 1937-02-06 1937-02-06 Process for the preparation of a chromium compound of the phthalein dye which is soluble in organic solvents containing hydroxyl groups from 2- [4'-dimethylamino-2'-oxybenzoyl] -benzoic acid and B-resorcylic acid. CH200544A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH197284T 1937-02-06
CH200544T 1937-02-06

Publications (1)

Publication Number Publication Date
CH200544A true CH200544A (en) 1938-10-15

Family

ID=25722968

Family Applications (1)

Application Number Title Priority Date Filing Date
CH200544D CH200544A (en) 1937-02-06 1937-02-06 Process for the preparation of a chromium compound of the phthalein dye which is soluble in organic solvents containing hydroxyl groups from 2- [4'-dimethylamino-2'-oxybenzoyl] -benzoic acid and B-resorcylic acid.

Country Status (1)

Country Link
CH (1) CH200544A (en)

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