DE950800C - Process for the production of dyes - Google Patents

Process for the production of dyes

Info

Publication number
DE950800C
DE950800C DEB32144A DEB0032144A DE950800C DE 950800 C DE950800 C DE 950800C DE B32144 A DEB32144 A DE B32144A DE B0032144 A DEB0032144 A DE B0032144A DE 950800 C DE950800 C DE 950800C
Authority
DE
Germany
Prior art keywords
parts
dyes
production
dye
trichlorobenzene
Prior art date
Legal status (The legal status 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 status listed.)
Expired
Application number
DEB32144A
Other languages
German (de)
Inventor
Dr Hellmuth Fischer
Dr Robert Gehm
Dr Curt Schuster
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Priority to DEB32144A priority Critical patent/DE950800C/en
Application granted granted Critical
Publication of DE950800C publication Critical patent/DE950800C/en
Expired legal-status Critical Current

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
    • C09B47/00—Porphines; Azaporphines
    • C09B47/04—Phthalocyanines abbreviation: Pc
    • 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
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/04—Isoindoline dyes

Landscapes

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

Description

Verfahren zur Herstellung von Farbstoffen Es wurde gefunden, daß man wertvolle Farbstoffe erhält, wenn man aromatische o-Dinitrile mit Amino-benzimidazolen erhitzt.Process for the preparation of dyes It has been found that valuable dyes are obtained when aromatic o-dinitriles with amino-benzimidazoles heated.

Die Umsetzung kann in der Schmelze durch einfaches Verbacken der Ausgangsstoffe bei Temperaturen von etwa i5o bis 2oo° vorgenommen werden oder auch durch Erhitzen der Ausgangsstoffe in Gegenwart eines hochsiedenden Lösungsmittels, wie Nitrobenzol, Trichlorbenzol oder o-Dichlorbenzol. Ein Zusatz von wasserfreien Alkaliacetaten, wie Natrium- oder Kaliumacetat, wirkt sich meistens günstig auf die Ausbeute aus. Im allgemeinen wird man i Mol des Dinitrils und i Mol des Aminobenzimidazols umsetzen, doch ist es oft zweckmäßig, die Aminoimidazolmenge etwas, größer zu wählen als die Dinitrilmenge.The reaction can be carried out in the melt by simply baking the starting materials be carried out at temperatures of about 150 to 200 ° or by heating the starting materials in the presence of a high-boiling solvent such as nitrobenzene, Trichlorobenzene or o-dichlorobenzene. An addition of anhydrous alkali acetates, like sodium or potassium acetate, usually has a positive effect on the yield. In general, one mole of the dinitrile and one mole of the aminobenzimidazole will be reacted, but it is often expedient to choose the amount of aminoimidazole somewhat greater than that Amount of dinitrile.

Man erhält wertvolle, im allgemeinen gelbe Pigmentfarbstoffe, die sich durch gute Echtheiten und große Farbstärke auszeichnen. Die Ausgiebigkeit bzw. die Farbstärke der erhaltenen Farbstoffe kann wesentlich erhöht werden, wenn man sie, zweckmäßig in Gegenwart eines Mahlhilfsstoffes, wie Natriumchlorid, vermahlt.Valuable, generally yellow pigment dyes are obtained are distinguished by good fastness properties and great color strength. The abundance or the color strength of the dyes obtained can be increased significantly if one they are ground, expediently in the presence of a grinding aid such as sodium chloride.

Die in den Beispielen genannten Teile sind Gewichtsteile.The parts mentioned in the examples are parts by weight.

Beispiel i 14 Teile o-Phthalodinitril werden mit 28 Teilen 2-Aminö-benzimidazol in 5oo Teilen Trichlorbenzol unter Rückflußkühlung 2 Stunden auf etwa 2oo° erhitzt. Nach dem Erkalten werden durch Abfiltrieren 13 Teile eines gelben Farbstoffes gewonnen, der mit Aceton gereinigt wird. Aus der Mutterlauge erhält man nach weitgehendem Entfernen des Lösungsmittels durch Wasserdampfdestillation-weitere 19 Teile des Farbstoffes. Er ergibt auf Polyamidfasern leuchtend gelbe Färbungen. Beispiel 2 14 Teile o-Phthalodinitril und 17 Teile i-Äthyl-2-amino-benzimidazol werden in 36o Teilen Trichlorbenzol 3 Stunden unter RückfluBkühlung gekocht. Beim Einengen der entstandenen Lösung kristallisieren 29 Teile eines Farbstoffes aus, der Polyamidfasern gelb färbt. Der Farbstoff eignet sich auch vorzüglich als Spinnfarbstoff, z. B. für Acetatkunstseide.Example i 14 parts of o-phthalonitrile are refluxed with 28 parts of 2-amino-benzimidazole in 500 parts of trichlorobenzene and heated to about 200 ° for 2 hours. After cooling, 13 parts of a yellow dye are obtained by filtering off, which is purified with acetone. After extensive removal of the solvent by steam distillation, a further 19 parts of the dye are obtained from the mother liquor. It produces bright yellow colorations on polyamide fibers. Example 2 14 parts of o-phthalonitrile and 17 parts of i-ethyl-2-aminobenzimidazole are refluxed in 360 parts of trichlorobenzene for 3 hours. When the resulting solution is concentrated, 29 parts of a dye crystallize out which dyes polyamide fibers yellow. The dye is also eminently suitable as a spin dye, e.g. B. for acetate rayon.

Claims (2)

PATENTANSPRÜCHE: i. Verfahren zur Herstellung von Farbstoffen, dadurch gekennzeichnet, daB man aromatische o-Dinitrile mit Amino-benzimidazolen erhitzt. PATENT CLAIMS: i. Process for the preparation of dyes, characterized in that aromatic o-dinitriles are heated with aminobenzimidazoles. 2. Verfahren nach Anspruch i, dadurch gekennzeichnet, daß man die Umsetzung in Gegenwart von wasserfreien Alkaliacetaten vornimmt.2. The method according to claim i, characterized in that one carries out the implementation in the presence of anhydrous alkali acetates.
DEB32144A 1954-08-07 1954-08-07 Process for the production of dyes Expired DE950800C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEB32144A DE950800C (en) 1954-08-07 1954-08-07 Process for the production of dyes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEB32144A DE950800C (en) 1954-08-07 1954-08-07 Process for the production of dyes

Publications (1)

Publication Number Publication Date
DE950800C true DE950800C (en) 1956-10-18

Family

ID=6963673

Family Applications (1)

Application Number Title Priority Date Filing Date
DEB32144A Expired DE950800C (en) 1954-08-07 1954-08-07 Process for the production of dyes

Country Status (1)

Country Link
DE (1) DE950800C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1229215B (en) * 1964-02-01 1966-11-24 Basf Ag Process for the production of dyes

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1229215B (en) * 1964-02-01 1966-11-24 Basf Ag Process for the production of dyes

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