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CH227509A - Process for the preparation of an azo dye. - Google Patents

Process for the preparation of an azo dye.

Info

Publication number
CH227509A
CH227509A CH227509DA CH227509A CH 227509 A CH227509 A CH 227509A CH 227509D A CH227509D A CH 227509DA CH 227509 A CH227509 A CH 227509A
Authority
CH
Switzerland
Prior art keywords
mol
preparation
acid
nitrodiazobenzene
parts
Prior art date
Application number
Other languages
German (de)
Inventor
Gesellschaft Fuer Chemis Basel
Original Assignee
Chem Ind Basel
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 Chem Ind Basel filed Critical Chem Ind Basel
Publication of CH227509A publication Critical patent/CH227509A/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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
    • C09B29/08—Amino benzenes

Landscapes

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

Description

  

  Verfahren     zur        Herstellung    eines     Azofarbstoffes.       Es wurde gefunden, dass man zu einem  neuen     Azofarbstoff    gelangen kann, wenn man  auf 1     Mol        Äthylogäthylaminobenzol    1     Mol          4-Nitrodiazobenzol    und 1     Mol        Sulfochlor-          essigsäure    derart zur     Einwirkung    bringt,

    dass das     4-Nitrodiazobenzol    in     4-Stellung    des       Äthylogäthylaminobenzols    eintritt und die       Chlorsulfonessigsäure    die     Ogäthylgruppe    un  ter Bildung eines sauren Esters     verestert.     



  Der neue Farbstoff bildet ein .scharlach  rotes Pulver, das sich in Wasser löst und       Acetatkunstseide    aus dem     neutralen        Glauber-          salzbade    in scharlachroten Tönen färbt.  



  <I>Beispiel:</I>  165     Teile        Äthylogäthylaminobenzol    wer  den in 1000     Vol.-Teilen        Toluol    gelöst, mit  260 Teilen     Sulfochloressigsäure    versetzt und  das Gemisch hierauf unter Rühren eine  Stunde lang zum Sieden erhitzt. Das mit  dem     Toluol    wegsiedende     Veresterungswasser     wird dabei getrennt aufgefangen, während  das überschüssige     Toluol    wieder in den Reak-         tionskolben    zurückfliesst. Nach beendigter  Umsetzung wird das     Toluol        abdestilliert    und  der Rückstand in 2000 Teilen Wasser gelöst.

    Die wässerige, allenfalls     filtrierte        Lösung     wird     nun    in üblicher Weise mit der     Diazo-          lösung    von 138 Teilen     4-Nitroaminobenzol     gekuppelt und die Mineralsäure mit Natrium  acetat abgestumpft. Der Farbstoff wird       abgenutsoht,    in Wasser nochmals auf  geschlämmt, mit Ammoniak genau neutral  gestellt, erneut     abgenutscht    und im Vakuum       getrocknet.     



  Zum gleichen Farbstoff     gelangt    man,  wenn man den     Azofarbstoff    aus 165 Teilen       Äthylogäthylaminobenzol    und .der     Diazover-          bindung    aus 138 Teilen     4-Nitroaminobenzol     herstellt und hierauf das so erhaltene Pro  dukt in     Toluol    mit 260 Teilen     Sulfochlor-          essigsäure    in der angegebenen Weise     ver-          estert.  



  Process for the preparation of an azo dye. It has been found that a new azo dye can be obtained if 1 mole of 4-nitrodiazobenzene and 1 mole of sulfochloroacetic acid are brought into action for 1 mole of ethyloethylaminobenzene,

    that the 4-nitrodiazobenzene occurs in the 4-position of the ethyloethylaminobenzene and the chlorosulfonacetic acid esterifies the Ogäthylgruppe under formation of an acidic ester.



  The new dye forms a scarlet red powder, which dissolves in water and dyes acetate artificial silk from the neutral Glauber salt bath in scarlet shades.



  <I> Example: </I> 165 parts of Ethylogäthylaminobenzene who dissolved in 1000 parts by volume of toluene, treated with 260 parts of sulfochloroacetic acid and the mixture is then heated to boiling for one hour while stirring. The esterification water that boils away with the toluene is collected separately, while the excess toluene flows back into the reaction flask. After the reaction has ended, the toluene is distilled off and the residue is dissolved in 2000 parts of water.

    The aqueous, if necessary filtered solution is then coupled in the usual way with the diazo solution of 138 parts of 4-nitroaminobenzene and the mineral acid is truncated with sodium acetate. The dye is sucked off, slurried again in water, made exactly neutral with ammonia, sucked off again and dried in vacuo.



  The same dyestuff is obtained if the azo dyestuff is prepared from 165 parts of ethyloethylaminobenzene and the diazo compound from 138 parts of 4-nitroaminobenzene and then the product thus obtained is esterified in toluene with 260 parts of sulfochloroacetic acid in the manner indicated.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Azo@farb- stoffes, dadurch gekennzeichnet, dass man auf 1 Mol Athyloxäthylaminobenzol 1 Mol 4-Nitrodiazobenzol und 1 Mol Sulfoehlor- essigsäure derart zur Einwirkung bringt, PATENT CLAIM: A process for the preparation of an azo @ dye, characterized in that 1 mol of 4-nitrodiazobenzene and 1 mol of sulfohaloacetic acid are brought into action for 1 mol of ethyloxethylaminobenzene dass das 4-Nitrodiazobenzol in 4-Stellung des Äthyloxäthylaminobenzols eintritt und die Chlorsulfonessigsäure die Oxäthylgruppe un ter Bildung eines sauren Esters verestert. Der neue Farbstoff bildet ein scharlach rotes Pulver, das sich in Wasser löst und Acetatkunstseide aus dem neutralen Glauber- salzbade in scharlachroten Tönen färbt. that the 4-nitrodiazobenzene occurs in the 4-position of the ethyloxethylaminobenzene and the chlorosulfonacetic acid esterifies the oxethyl group under formation of an acidic ester. The new dye forms a scarlet red powder, which dissolves in water and dyes acetate silk from the neutral Glauber's salt bath in scarlet shades.
CH227509D 1941-05-29 1941-05-29 Process for the preparation of an azo dye. CH227509A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH225362T 1941-05-29
CH227509T 1941-05-29

Publications (1)

Publication Number Publication Date
CH227509A true CH227509A (en) 1943-06-15

Family

ID=25726859

Family Applications (1)

Application Number Title Priority Date Filing Date
CH227509D CH227509A (en) 1941-05-29 1941-05-29 Process for the preparation of an azo dye.

Country Status (1)

Country Link
CH (1) CH227509A (en)

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