CH211050A - Process for the preparation of a chromable triarylmethane dye. - Google Patents

Process for the preparation of a chromable triarylmethane dye.

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Publication number
CH211050A
CH211050A CH211050DA CH211050A CH 211050 A CH211050 A CH 211050A CH 211050D A CH211050D A CH 211050DA CH 211050 A CH211050 A CH 211050A
Authority
CH
Switzerland
Prior art keywords
dye
preparation
chromable
weight
parts
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 CH211050A publication Critical patent/CH211050A/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
    • C09B11/22—Amino derivatives of triarylmethanes containing OH groups bound to an aryl nucleus and their ethers and esters

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

Description

  

  <B>Zusatzpatent</B> zum     Hauptpatent    Nr. 209344    Verfahren zur Herstellung eines     ehromierbaren        Triarylmethanfarbstoffes.       Gegenstand dieses     Zusatzpatentes    ist ein  Verfahren zur Herstellung eines     chromier-          baren        Triarylmethanfarbstoffes,    welches darin  besteht,

   dass man 1     Mol        2-Sulfo-4-oxy-5-          carboxybenzaldehyd    mit 2     Mol        N-Butyl-o-          toluidin        kondensiert    und die so     erhaltene          Leukoverbindung    des     Farbstoffes    oxydiert.  



  Der so erhaltene neue     Farbstoff    färbt in  Form des     Natriumsalzes    Wolle und Seide in  saurem Bade in reinen grünen Tönen.     Durch          Naehchromieren    wird der Farbton etwas nach  Blau verschoben, und die Echtheitseigen  schaften werden     verbessert.     



       Beispiel:     81 Gewichtsteile     4-Oxy-5-carboxybenz-          a.ldehyd-2-sulfosaures        Natrium    werden zu  sammen mit 108     Gewichtsteilen        N-Butyl-o-          toluidin    in 300 Gewichtsteilen 10     %        iger     Schwefelsäure so lange auf etwa 95   C er  hitzt, bis die     Kondensation    beendet ist,     was          etwa    80 Stunden in Anspruch nimmt.

   Die in    Wasser unlösliche     Leukosäure    wird mit Soda  in Wasser neutral     gelöst    und in     bekannter          Weise    zum Beispiel mit     Bleisup-eroxyd    in       Gegenwart    einer     Säure    zum     Farbstoff    oxy  diert. Der     isolierte    Farbstoff färbt     als        Na-          triumsalz        Wolle    und Seide in saurem     Bade          in,    reinen grünen Tönen.

   Durch     Nachchromie-          ren    wird der Farbton     etwas    nach Blau ver  schoben, und die     Echtheitseigenschaften    wer  den     verbessert.     



  Die als     Ausgangsstoff        verwendete        4-Oxy-          5-ca"rboxybenzal,dehyd-2-sulf        onsäure    kann auf  folgende Weise erhalten werden.  



  173     Gewichtsteile        4-Chlor-2-oxybenzoe-          säure    werden in einer Lösung von 400 Ge  wichtsteilen     Ätznatron    in 445     Gewichtsteilen     Wässer auf 65   C erhitzt. Zu dieser Lösung  lässt man 230     Gewichtsteile    Chloroform bei  einer Temperatur von<B>65-70'</B> C zulaufen  und erhitzt dann noch 8 Stunden auf<B>70'</B> C.

    Aus     der    so erhaltenen Lösung     gewinnt    man  durch     Ansäuern    den 2-Chlor-4.5-oxy=carb-           oxybenzaldehyd,    den man über seine     Bisulfit-          verbindung    reinigen und von     unveränderten     Ausgangsmaterialien befreien kann.

   223 Ge  wichtsteile des     NatriumsaIzes    des so erhal  tenen Aldehyds     werden    mit einer konzen  trierten     wässrigen    Lösung von 130 Gewichts  teilen     Natrium.sulfit    7     Stunden    im     Autokla-          ven    auf 160   C erhitzt. Aus der so erhal  tenen klaren Lösung erhält man durch An  säuern den     2-Sulfo-4-oxy-5-carboxybenzalde-          hyd    in Form seines sauren     Natriumsalzes.  



  <B> Additional patent </B> to main patent no. 209344 Process for the production of an honorable triarylmethane dye. The subject of this additional patent is a process for the production of a chromable triarylmethane dye, which consists in

   that 1 mol of 2-sulfo-4-oxy-5-carboxybenzaldehyde is condensed with 2 mol of N-butyl-o-toluidine and the leuco compound of the dye thus obtained is oxidized.



  The new dye thus obtained, in the form of the sodium salt, dyes wool and silk in an acid bath in pure green tones. After chroming, the hue is shifted slightly towards blue and the fastness properties are improved.



       Example: 81 parts by weight of 4-oxy-5-carboxybenz- a.ldehyd-2-sulfonic acid sodium are heated to about 95 C together with 108 parts by weight of N-butyl-o-toluidine in 300 parts by weight of 10% sulfuric acid until condensation has ended, which takes about 80 hours.

   The water-insoluble leuco acid is dissolved neutrally in water with soda and oxidized in a known manner, for example with lead superoxide in the presence of an acid, to form the dye. The isolated dye, as the sodium salt, dyes wool and silk in an acid bath in pure green tones.

   After chrome plating, the color is shifted slightly towards blue and the fastness properties are improved.



  The 4-oxy-5-ca "rboxybenzal, dehyd-2-sulfonic acid used as the starting material can be obtained in the following manner.



  173 parts by weight of 4-chloro-2-oxybenzoic acid are heated to 65 ° C. in a solution of 400 parts by weight of caustic soda in 445 parts by weight of water. 230 parts by weight of chloroform are allowed to run into this solution at a temperature of <B> 65-70 '</B> C and then heated to <B> 70' </B> C for a further 8 hours.

    The solution obtained in this way is acidified to obtain 2-chloro-4,5-oxy = carbo-oxybenzaldehyde, which can be purified via its bisulfite compound and freed from unchanged starting materials.

   223 parts by weight of the sodium salt of the aldehyde obtained in this way are heated to 160 C for 7 hours in an autoclave with a concentrated aqueous solution of 130 parts by weight of sodium sulfite. The clear solution obtained in this way is obtained by acidifying the 2-sulfo-4-oxy-5-carboxybenzaldehyde in the form of its acidic sodium salt.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines eliminier baren Triary linethanfarbstoffes, dadurch ge kennzeichnet dass man 1Mo1 ?-Sulfo-4-oxy- 5-carboxybenzaldehyd mit<B>-9-</B> 111o1 N-Butyl-o- toliii < lin kondensiert und die so erhaltene Leukoverbindung des Farbstoffes oxydiert. Der so erhaltene neue Farbstoff färbt in Form des Natriumsalzes Wolle und Seide in saurem Bade in reinen grünen Tönen. PATENT CLAIM: Process for the preparation of an eliminable triary linethane dye, characterized in that 1Mo1? -Sulfo-4-oxy-5-carboxybenzaldehyde is condensed with <B> -9- </B> 111o1 N-butyl-o-toliii <lin and oxidizing the leuco compound of the dye thus obtained. The new dye thus obtained, in the form of the sodium salt, dyes wool and silk in an acid bath in pure green tones. Durch Naehehromieren wird der Farbton etwas nach Blau verschoben, und die Echtheitseigen- schaffen werden verbessert. UN-TERANSPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man die Komponenten in Gegenwart von 10%iger Schwefelsäure auf etwa 95 " C erhitzt. The hue is shifted slightly towards blue by close-fitting, and the authenticity properties are improved. UN-TERM CLAIM: Process according to patent claim, characterized in that the components are heated to about 95 ° C in the presence of 10% sulfuric acid.
CH211050D 1937-11-03 1938-08-29 Process for the preparation of a chromable triarylmethane dye. CH211050A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE211050X 1937-11-03
CH209344T 1938-08-29

Publications (1)

Publication Number Publication Date
CH211050A true CH211050A (en) 1940-08-15

Family

ID=25724698

Family Applications (1)

Application Number Title Priority Date Filing Date
CH211050D CH211050A (en) 1937-11-03 1938-08-29 Process for the preparation of a chromable triarylmethane dye.

Country Status (1)

Country Link
CH (1) CH211050A (en)

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