DE665557C - Process for the representation of dyes - Google Patents

Process for the representation of dyes

Info

Publication number
DE665557C
DE665557C DEI41347D DEI0041347D DE665557C DE 665557 C DE665557 C DE 665557C DE I41347 D DEI41347 D DE I41347D DE I0041347 D DEI0041347 D DE I0041347D DE 665557 C DE665557 C DE 665557C
Authority
DE
Germany
Prior art keywords
dyes
representation
aralkyl
alkyl
radical
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
DEI41347D
Other languages
German (de)
Inventor
Dr Ottmar Wahl
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.)
IG Farbenindustrie AG
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
Priority to DEI41347D priority Critical patent/DE665557C/en
Application granted granted Critical
Publication of DE665557C publication Critical patent/DE665557C/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
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/14—Styryl dyes
    • C09B23/143—Styryl dyes the ethylene chain carrying a COOH or a functionally modified derivative, e.g.-CN, -COR, -COOR, -CON=, C6H5-CH=C-CN

Landscapes

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

Description

Verfahren zur Darstellung von Farbstoffen Es wurde gefunden, daß man zu wertvollen Farbstoffen der allgemeinen Formel worin R, und R. Wasserstoff, einen Alkyl-, Aralkyl- oder Arylrest und R3 eine Alkoxygruppe oder den Rest eines aromatischen Amins bedeuten und worin der Benzolkern ferner substituiert sein kann, gelangt, wenn man einen Cyanessigester oder ein Cyanessigsäurearylid mit einer äquitnolekularen Menge eines aromatischen p-Amidoaldehyds, der in der Amidogruppe durch Alkyl, Aralkyl oder Aryl ersetzt sein kann, bzw. seiner Benzylidenverbindungen kondensiert. Die so erhältlichen 1' arbstoffe eignen sich zum Färben von Celluloseestern. wird mit Cyanessigsäureäthylester in molekularen Verhältnissen, wie in Beispiel i ange- der aus Alkohol mit dem Schmelzpunkt 125' auskristallisiert. Er färbt Acetatseide etwas Beispiel i Cyanessigsäureäthylester und p-Diäthylamidobenzaldehyd werden in molekularen Mengen zweckmäßig in einem Lösungsmittel, z. B. Alkohol, gelöst und die Reaktion durch Zusatz einer Spur Alkali, wie z. B. Piperidin, eingeleitet, evtl. durch Erwärmen beschleunigt. Der gebildete gelbe Farbstoff läßt sich aus Alkohol in schönen Kristallen vom Schmelzpunkt 95° kristallisieren. Er färbt f. B. Acetatseide in sehr klaren, gelben Tönen von sehr guter Lichtechtheit.Process for the preparation of dyes It has been found that valuable dyes of the general formula can be obtained wherein R, and R. are hydrogen, an alkyl, aralkyl or aryl radical and R3 is an alkoxy group or the radical of an aromatic amine and in which the benzene nucleus can also be substituted, if you get a cyanoacetic ester or a cyanoacetic acid arylide with an equitmolecular amount of one aromatic p-amidoaldehyde, which can be replaced in the amido group by alkyl, aralkyl or aryl, or its benzylidene compounds are condensed. The 1 'dyes obtainable in this way are suitable for dyeing cellulose esters. is with ethyl cyanoacetate in molecular proportions, as in Example i which crystallizes from alcohol with a melting point of 125 '. He dyes acetate silk something example i ethyl cyanoacetate and p-diethylamidobenzaldehyde are expediently in molecular amounts in a solvent, eg. B. alcohol, dissolved and the reaction by adding a trace of alkali, such as. B. piperidine, initiated, possibly accelerated by heating. The yellow dye formed can be crystallized from alcohol in beautiful crystals with a melting point of 95 °. It dyes eg acetate silk in very clear, yellow shades of very good lightfastness.

Beispiel 2 Die Benzylidenverbindung vom p-Dimetlivlamidobenzaldehyd mit urisym. p-Dimethylami dophenylendiamin geben., behandelt. Es bildet sich neben unsym.. Dimethyl-p-phenylendiamin der gelbe Farbstoff grünstichiger als der in Beispiel i beschriebene Farbstoff an. p-Diäthylamidobenzaldehyd und Cyanessig-,@@ säureanilid werden in molekularen Verhäär ;pissen, wie in Beispiel i angegeben, behan-`tie,lt. Es bildet sich der gelbe Farbstoff: der aus Alkohol mit dem Schmelzpunkt i8o° kristallisiert.Example 2 The benzylidene compound of p-Dimetlivlamidobenzaldehyd with urisym. give p-Dimethylami dophenylenediamine., treated. In addition to unsym. Dimethyl-p-phenylenediamine, the yellow dye is formed with a greener cast than the dye described in Example i. p-Diethylamidobenzaldehyde and cyanoacetic acid, @@ acid anilide are treated in molecular conditions; piss, as stated in example i, according to The yellow dye is formed: which crystallizes from alcohol with a melting point of 180 °.

Claims (1)

PATEN TANSPRUCH Verfahren zur Darstellung von Farbstoffen der allgemeinen Formel: worin R1 und R2 Wasserstoff, einen Alkyl-, Aralkyl- oder Arylrest und R, eine Alkoxygruppe oder den Rest eines aromatischen Amins bedeuten und worin der Benzolkern ferner substituiert sein kann, dadurch gekennzeichnet, daß man einen Cyanessigester oder ein Cyanessigsäurearylid mit einer äquimolekularen Menge eines aromatischen p-Amidoaldehyds, der in der Amidogruppe durch Alkyl, Aralkyl oder Aryl besetzt sein kann, bzw. seiner Benzylidenverbindungen kondensiert.PATENT CLAIM Process for the representation of dyes of the general formula: wherein R1 and R2 are hydrogen, an alkyl, aralkyl or aryl radical and R, an alkoxy group or the radical of an aromatic amine and in which the benzene nucleus can furthermore be substituted, characterized in that a cyanoacetic ester or a cyanoacetic acid arylide with an equimolecular amount of one aromatic p-amidoaldehyde, which can be occupied by alkyl, aralkyl or aryl in the amido group, or its benzylidene compounds are condensed.
DEI41347D 1931-04-22 1931-04-23 Process for the representation of dyes Expired DE665557C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEI41347D DE665557C (en) 1931-04-22 1931-04-23 Process for the representation of dyes

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE1950421X 1931-04-22
DEI41347D DE665557C (en) 1931-04-22 1931-04-23 Process for the representation of dyes

Publications (1)

Publication Number Publication Date
DE665557C true DE665557C (en) 1938-09-28

Family

ID=25981641

Family Applications (1)

Application Number Title Priority Date Filing Date
DEI41347D Expired DE665557C (en) 1931-04-22 1931-04-23 Process for the representation of dyes

Country Status (1)

Country Link
DE (1) DE665557C (en)

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