DE716976C - Process for the preparation of perylene series dyes - Google Patents
Process for the preparation of perylene series dyesInfo
- Publication number
- DE716976C DE716976C DEI58055D DEI0058055D DE716976C DE 716976 C DE716976 C DE 716976C DE I58055 D DEI58055 D DE I58055D DE I0058055 D DEI0058055 D DE I0058055D DE 716976 C DE716976 C DE 716976C
- Authority
- DE
- Germany
- Prior art keywords
- preparation
- perylene series
- dyes
- perylene
- series dyes
- 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
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
- C09B3/00—Dyes with an anthracene nucleus condensed with one or more carbocyclic rings
- C09B3/02—Benzathrones
- C09B3/06—Preparation from starting materials already containing the benzanthrone nucleus
- C09B3/10—Amino derivatives
-
- 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
- C09B3/00—Dyes with an anthracene nucleus condensed with one or more carbocyclic rings
- C09B3/14—Perylene derivatives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Description
Verfahren zur Herstellung von Farbstoffen der Perylenreihe Gegenstand des Patents 710 409 ist ein Verfahren zur Herstellung von Farbstoffen der Perylenreihe, bei dem man Oxyv erbindungen der Perylen- oder Azapeiylenreihe mit höher molekularen ungesättigten Kohlemvasserstoffen oder von diesen durch Anlagerung von Wasser, Schwefelwasserstoff, Säuren, Alkoholen, Mercaptanen oder Aminen abgeleiteten Verbindungen in Gegenwart vonKondensationsmitteln erhitzt. An Stelle der Oxyverbindungen kann man auch r-,etone der Perylen-oder Azaperylenreihe verwenden, die unter den Umsetzungsbedingungen in Oxyverbindungen dieser Reihen übergehen.Process for the production of dyes of the perylene series The subject of patent 710 409 is a process for the production of dyes of the perylene series, in which one oxyv compounds of the perylene or azapeiylene series with higher molecular weight unsaturated hydrocarbons or from these by addition of water, hydrogen sulfide, acids, alcohols , Mercaptans or amines derived compounds are heated in the presence of condensing agents. Instead of the oxy compounds, it is also possible to use r, etones of the perylene or azaperylene series, which convert into oxy compounds of this series under the reaction conditions.
Es wurde nun gefunden, daß ähnliche Endstoffe erhalten werden, wenn man das unter den L msetzungsbedingtmgen in eine Oxyverbindung der Pervlenreihe übergehende 2, a'-Dibenzanthronyl dieser Behandlung unterwirft. In Gegenwart von Zinkchlorid erhält man z. B. mit Dodecylbromid denselben Endstoff wie nach Beispiel i Abs, i des Hauptpatents.It has now been found that similar end products are obtained when one that under the conditions of settlement in an oxy compound of the Pervlen series submitting transient 2, a'-dibenzanthronyl to this treatment. In the presence of Zinc chloride is obtained z. B. with dodecyl bromide the same end product as in the example i Para, i of the main patent.
Es ist bekannt, durch Einwirkung von Ole-'-finen oder halogenierten Pa.raffinkohlenwa.sserstoffen auf aromatische Kohlenwasserstoff e, wie Naphthalin, Anthracen oder Phenanthren, Farbstoffe herzustellen, die in organischen Lösungsmitteln leicht löslich sind und in diesen Mitteln auch fluoreszieren. Es sind aber verhältnismäßig große Mengen jener Stoffe notwendig, um eine merkbare Fluoreszenz zu erzielen. Demgegenüber färben die neuen Verbindungen organische Mittel schon in sehr kleinen Mengen kräftig' und erteilen ihnen eine kräftige Fluoreszenz.It is known by the action of olefins or halogenated Pa.raffin coal hydrocarbons to aromatic hydrocarbons, such as naphthalene, Anthracene or phenanthrene to manufacture dyes in organic solvents are easily soluble and also fluoresce in these agents. But they are proportionate large amounts of these substances are necessary to achieve a noticeable fluorescence. In contrast the new compounds give organic agents a strong color even in very small quantities' and give them a strong fluorescence.
Beispiel Eine Mischung aus I oo Teilen D.odecylbromid, 2o Teilen 2, ^_'-Dibenzanthronyl und 5o Teilen Zinkchlorid erhitzt man so lange auf zoo bis 22o°, bis der ,Ausgangsstoff verschwunden ist. Dann läßt man das Gemisch abkühlen, verdünnt es mit aoo Teilen Benzol, saugt von ungelösten Anteilen ab und wäscht den Rückstand mit Benzol aus. Die Benzollösung dampft man ein und erhitzt den öligen Rückstand unter vermindertem Druck. Hierbei geht ein farbloser, paraffinölartiger Stoff über, während in vorzüglicher Ausbeute ein in der Wärme leicht bewegliches, tiefrotes Öl zurückbleibt, das sich z. B. in Paraffinöl sehr leicht löst. Die Lösung ist rötlichgelb und besitzt eine sehr kräftige olivestichiggelb.e Fluoreszenz.Example A mixture of 10 parts of D.odecyl bromide, 2 parts of 2, ^ _'- Dibenzanthronyl and 50 parts of zinc chloride are heated to zoo to 22o ° for so long, until the raw material has disappeared. The mixture is then allowed to cool, diluted it with aoo parts of benzene, sucks off undissolved components and washes the residue with benzene. The benzene solution is evaporated and the oily residue is heated under reduced pressure. A colorless, paraffin oil-like substance passes over here, while in excellent yield a deep red one which is easily mobile in the warmth Oil remains, which z. B. dissolves very easily in paraffin oil. The solution is reddish yellow and has a very strong olive-tinged yellow fluorescence.
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEI58055D DE716976C (en) | 1936-09-16 | 1936-09-16 | Process for the preparation of perylene series dyes |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEI58055D DE716976C (en) | 1936-09-16 | 1936-09-16 | Process for the preparation of perylene series dyes |
Publications (1)
Publication Number | Publication Date |
---|---|
DE716976C true DE716976C (en) | 1942-02-03 |
Family
ID=7194688
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEI58055D Expired DE716976C (en) | 1936-09-16 | 1936-09-16 | Process for the preparation of perylene series dyes |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE716976C (en) |
-
1936
- 1936-09-16 DE DEI58055D patent/DE716976C/en not_active Expired
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