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DE447754C - Process for the production of post-chromable dyes - Google Patents

Process for the production of post-chromable dyes

Info

Publication number
DE447754C
DE447754C DEC36947D DEC0036947D DE447754C DE 447754 C DE447754 C DE 447754C DE C36947 D DEC36947 D DE C36947D DE C0036947 D DEC0036947 D DE C0036947D DE 447754 C DE447754 C DE 447754C
Authority
DE
Germany
Prior art keywords
dyes
parts
acid
chromable
post
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
DEC36947D
Other languages
German (de)
Inventor
Dr Hans Grotomsky
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 DEC36947D priority Critical patent/DE447754C/en
Application granted granted Critical
Publication of DE447754C publication Critical patent/DE447754C/en
Expired legal-status Critical Current

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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
    • C09B11/26—Triarylmethane dyes in which at least one of the aromatic nuclei is heterocyclic

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

Description

Verfahren zur Herstellung nachchromierbarer Farbstoffe. Es ist bekannt, daß sich aromatische Aldehyde mit je i Mol. zweier verschiedener Oxycarbonsäuren zu Leukoverbindungen nachchromierbarer Farbstoffe kondensieren lassen. Farbstoffe dieser Reihe, die an Stelle der einen Oxycarbonsäuregruppe einen andersartigen Rest enthalten, sind bisher nur vereinzelt und nicht von Aldehyden ausgehend erhalten worden.Process for the production of post-chromable dyes. It is known, that there are aromatic aldehydes with i mole each of two different oxycarboxylic acids condense to form leuco compounds that can be chromated. Dyes this series, which has a different type of radical in place of one oxycarboxylic acid group contain, are so far only sporadically and not obtained starting from aldehydes been.

Es wurde die überraschende Beobachtung gemacht, daß besonders wertvolle Farbstoffe entstehen, wenn man beliebige Aldehyde mit i Mol. einer Oxycarbonsäure und i Mol. einer herterozyklischen, reaktionsfähige CH,-oder CH-Gruppen enthaltenden Verbindung kondensiert und die erhaltenen Leukosäuren in bekannter Weise zu den Farbstoffen oxydiert. Man kann entweder in der Weise vorgehen, daß man zunächst den Aldehyd mit der einen Komponente zum Hydrol vereinigt und dieses letztere mit der zweiten Komponente kondensiert, oder man kann in einem einzigen Arbeitsgang unmittelbar durch Kondensation des Aldehyds mit einem Gemisch der beiden Komponenten die Leukoverbindung gewinnen.The surprising observation was made that particularly valuable Dyes are formed if any aldehydes are mixed with one mole of an oxycarboxylic acid and i mole of a heterocyclic, reactive CH, or CH group containing Compound condensed and the leuco acids obtained in a known manner to the Oxidized dyes. One can either proceed in such a way that one first the aldehyde is combined with one component to form the hydrol and the latter with the second component is condensed, or it can be done in a single operation directly by condensation of the aldehyde with a mixture of the two components win the leuco connection.

Beispiel i.Example i.

175 Gewichtsteile 2-6-Dichlorbenzaldehyd werden mit i52 Gewichtsteilen o-Kresotinsäure und 116 Gewichtsteilen Dioxythiazol in 2 5oo Teilen konzentrierter Schwefelsäure gelöst und die Lösung 2,4 Stunden lang bei gewöhnlicher Temperatur gerührt. Zur Oxydation der entstandenen Leukosäure setzt man die nötige Menge Natriumnitrit hinzu und isoliert darauf den Farbstoff in bekannter Weise in Gestalt seines Natronsalzes. Die Färbung auf Wolle gibt beim Nachchromieren ein Blau von hervorragenden Echtheitseigenschaften. 175 parts by weight of 2-6-dichlorobenzaldehyde are dissolved with i52 parts by weight of o-cresotinic acid and 116 parts by weight of dioxythiazole in 2,500 parts of concentrated sulfuric acid and the solution is stirred for 2.4 hours at ordinary temperature. To oxidize the leuco acid formed, the necessary amount of sodium nitrite is added and the dye is then isolated in a known manner in the form of its sodium salt. The dyeing on wool gives a blue with excellent fastness properties when it is re-chromed.

Beispiele. 186 Teile Benzaldehyd-o-sulfosäure, 152 Teile o-Kresotinsäure und 128 Teile Barbitursäure werden in 3 ooo Teilen konzentrierter Schwefelsäure im Verlauf von 2d. Stunden zur Leukosäure kondensiert und diese durch Zugabe der erforderlichen Menge Natriumnitrit zur Farbsäure oxydiert. Der in Form seines sehr leicht löslichen Natronsalzes gewonnene Farbstoff färbt Wolle aus saurem Bade rot; beim Nachchromieren schlägt die Farbe in ein rotstichiges Blau um.Examples. 186 parts of benzaldehyde-o-sulfonic acid, 152 parts of o-cresotinic acid and 128 parts of barbituric acid are dissolved in 3,000 parts of concentrated sulfuric acid in the course of 2d. Hours condensed to the leuco acid and this by adding the required amount of sodium nitrite is oxidized to color acid. The one in the form of his very Dye obtained from easily soluble sodium salt dyes wool from acid baths red; when chrome plating, the color changes to a reddish blue.

Beispiel 3. Example 3.

i75 Teile 2-6-Dichlorbenzaldehyd werden mit 152 Teilen. o-Kresotinsäure und 174 Teilen Phenylmethylpyrazolon in 3 0öo Teilen Schwefelsäure gelöst und, wie in Beispiel 2 angegeben, weiterbehandelt. Dier erhaltene Farbstoff färbt Wolle braunrot, nachchromiert. marineblau.175 parts of 2-6-dichlorobenzaldehyde are combined with 152 parts. o-cresotinic acid and 174 parts of phenylmethylpyrazolone dissolved in 3 0öo parts of sulfuric acid and how in example 2 specified, further treated. The obtained dye dyes wool brown-red, chromed. navy blue.

Claims (1)

PATENTANSYRUCIi: Verfahren zur -Herstellung nachchromierbarer Farbstoffe, darin bestehend, daB ein Aldehyd mit i Mol. einer o-Oxycarbonsäure und i Mol. einer heterozyklischen, eine reaktionsfähige CH,- oder CH-Gruppe enthaltenden Verbindung kondensiert und die erhaltene Leukoverbindung in bekannter Weise zum Farbstoff oxydiert wird.PATENTANSYRUCIi: Process for the production of post-chromable dyes, consisting in that an aldehyde condenses with one mole of an o-oxycarboxylic acid and one mole of a heterocyclic compound containing a reactive CH, or CH group and the leuco compound obtained is condensed in a known manner to Dye is oxidized.
DEC36947D 1925-07-14 1925-07-14 Process for the production of post-chromable dyes Expired DE447754C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEC36947D DE447754C (en) 1925-07-14 1925-07-14 Process for the production of post-chromable dyes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEC36947D DE447754C (en) 1925-07-14 1925-07-14 Process for the production of post-chromable dyes

Publications (1)

Publication Number Publication Date
DE447754C true DE447754C (en) 1927-08-02

Family

ID=7022560

Family Applications (1)

Application Number Title Priority Date Filing Date
DEC36947D Expired DE447754C (en) 1925-07-14 1925-07-14 Process for the production of post-chromable dyes

Country Status (1)

Country Link
DE (1) DE447754C (en)

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