DE3533545A1 - Isoindoline dyes - Google Patents

Isoindoline dyes

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Publication number
DE3533545A1
DE3533545A1 DE19853533545 DE3533545A DE3533545A1 DE 3533545 A1 DE3533545 A1 DE 3533545A1 DE 19853533545 DE19853533545 DE 19853533545 DE 3533545 A DE3533545 A DE 3533545A DE 3533545 A1 DE3533545 A1 DE 3533545A1
Authority
DE
Germany
Prior art keywords
phenylcarbamoyl
formula
dyes
ring
isoindoline
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.)
Withdrawn
Application number
DE19853533545
Other languages
German (de)
Inventor
Wolfgang Dr Lotsch
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 DE19853533545 priority Critical patent/DE3533545A1/en
Publication of DE3533545A1 publication Critical patent/DE3533545A1/en
Withdrawn legal-status Critical Current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
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/04—Isoindoline dyes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
    • C08K5/3432—Six-membered rings
    • C08K5/3437—Six-membered rings condensed with carbocyclic rings

Abstract

Isoindoline dyes of the formula <IMAGE> where R is cyano, C1-C4-alkoxycarbonyl, phenoxycarbonyl, N-C1-C4-alkylcarbamoyl, N-phenylcarbamoyl, 2-quinazolonyl, 2-quinoxalinonyl, 2-benzimidazolyl or 2-benzothiazolyl and the ring A, the quinoline ring system, the phenyl rings in R and the benzene rings in the heterocyclic radicals in R may be substituted by non-solubilising groups, are highly suitable for dyeing polyolefins and are useful dyes for the mass coloration of thermoplastics. They produce bright yellow to orange shades which have good fastness properties.

Description

Aus der DE-OS 26 15 394 sind Kondensationsprodukte aus Diiminoisoindolin mit einem Molekül eines Cyanacetamids und einem Molekül eines Anilins bekannt. Sie können zum Spinnfärben von Polyesterfasern verwendet werden. Für die Massefärbung von Polyolefinen genügen ihre Migrationsechtheiten nicht höchsten Anforderungen.DE-OS 26 15 394 are condensation products made from diiminoisoindoline with a molecule of a cyanoacetamide and a molecule of aniline. They can be used for spin dyeing polyester fibers. Their migration fastnesses are sufficient for the mass coloring of polyolefins not the highest demands.

Aufgabe der Erfindung war es, Indolinfarbstoffe bereitzustellen, die diese Nachteile nicht zeigen.The object of the invention was to provide indoline dyes that Do not show disadvantages.

Es wurde gefunden, daß Isoindolinfarbstoffe der Formel (I) in der R Cyan, C1- bis C4-Alkoxycarbonyl, Phenoxycarbonyl, N-C1- bis C4- Alkylcarbamoyl, N-Phenylcarbamoyl, Chinazolonyl-2, Chinoxalinonyl-2, Benzimidazolyl-2, oder Benzthiazolyl-2 bedeuten und der Ring A, das Chinolinringsystem, die Phenylringe in R und die Benzringe in den heterocyclischen Resten in R gegebenenfalls durch nichtlöslich machende Gruppen substituiert sind, hervorragend zum Färben von Polyolefinen geeignet sind.It has been found that isoindoline dyes of the formula (I) in which R is cyan, C 1 - to C 4 -alkoxycarbonyl, phenoxycarbonyl, NC 1 - to C 4 - alkylcarbamoyl, N-phenylcarbamoyl, quinazolonyl-2, quinoxalinonyl-2, benzimidazolyl-2, or benzothiazolyl-2 and the ring A , the quinoline ring system, the phenyl rings in R and the benz rings in the heterocyclic radicals in R are optionally substituted by non-solubilizing groups, are outstandingly suitable for dyeing polyolefins.

Die Farbstoffe der Formel (I) sind wertvolle Farbstoffe, die sich durch klare Farbtöne und gute Echtheiten auszeichnen und die sich sehr gut zum Färben von thermoplastischen Kunststoffen eignen.The dyes of the formula (I) are valuable dyes which are characterized by distinguish clear colors and good fastness properties and which are very good for Suitable for coloring thermoplastics.

Als nichtlöslich machende Substituenten kommen am Ring A, dem Chinolinringsystem, dem Phenylrest in R und den Benzringen der heterocyclischen Reste in R z. B. C1- bis C4-Alkyl, C1- bis C4-Alkoxy, Halogen wie Fluor, Chlor und Brom, C1- bis C4-Alkoxycarbonyl, Nitro, Hydroxy, Acetylamino und/oder Trifluormethyl in Betracht. As non-solubilizing substituents on ring A, the quinoline ring system, the phenyl radical in R and the benz rings of the heterocyclic radicals in R z. B. C 1 - to C 4 -alkyl, C 1 - to C 4 -alkoxy, halogen such as fluorine, chlorine and bromine, C 1 - to C 4 -alkoxycarbonyl, nitro, hydroxy, acetylamino and / or trifluoromethyl.

Von den Verbindungen der Formel (I) sind solche bevorzugt, bei denen der Chinolinring entweder unsubstituiert oder in 3-Stellung durch Hydroxy oder in 4-Stellung durch Methyl substituiert ist und der Ring A keine Substituenten trägt.Of the compounds of formula (I) those are preferred in which the Quinoline ring either unsubstituted or in the 3-position by hydroxy or is substituted in the 4-position by methyl and ring A has no substituents wearing.

Von den letztgenannten Farbstoffen der Formel (I) sind solche besonders hervorzuheben, bei denen R für gegebenenfalls durch nichtlöslich machende Gruppen substituiertes N-Phenylcarbamoyl steht.Of the latter dyes of the formula (I), those are special to emphasize, where R for possibly by non-solubilizing Substituted N-phenylcarbamoyl.

Ganz besonders bevorzugt sind Farbstoffe der Formel (I), in der der Chinolinrest unsubstituiert oder in 3-Stellung durch Hydroxy oder in 4-Stellung durch Methyl substituiert ist, der Ring A unsubstituiert ist und R für durch Methyl, Ethyl, Methoxy, Ethoxy, Methoxycarbonyl, Ethoxycarbonyl, Trifluormethyl, Fluor, Chlor oder Brom einfach substituiertes N-Phenylcarbamoyl steht.Dyes of the formula (I) in which the quinoline radical are very particularly preferred unsubstituted or in the 3-position by hydroxy or in the 4-position is substituted by methyl, ring A is unsubstituted and R is by methyl, ethyl, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, Trifluoromethyl, fluorine, chlorine or bromine monosubstituted N-phenylcarbamoyl stands.

Die Herstellung der neuen Farbstoffe erfolgt nach bekannten Verfahren durch Kondensation einer 1-[Cyanmethylen]-3-iminoisoindolin-Verbindung (II) mit einem Molekül eines Aminochinolins der Formel (III) unter Abspaltung von Ammoniak.The new dyes are prepared by known processes by condensation of a 1- [cyanomethylene] -3-iminoisoindoline compound (II) with a molecule of an aminoquinoline of the formula (III) with the release of ammonia.

In der Formel (II) hat R die oben angegebene Bedeutung. Die Ringe A und das Chinolinsystem in (III) können, wie oben angegeben, substituiert sein. In formula (II), R has the meaning given above. The rings A and the quinoline system in (III) can be substituted as indicated above.  

Die Umsetzung der 1-[Cyanmethylen]-3-iminoisoindolin-Verbindung (II) mit dem Aminochinolin (III) erfolgt in wasserfreien Lösungsmitteln bei erhöhter Temperatur. In der Regel genügen Temperaturen zwischen 50°C und 140°C. Als Lösungsmittel können z. B. niedere aliphatische Karbonsäuren wie Essigsäure oder Propionsäure verwendet werden.The reaction of the 1- [cyanomethylene] -3-iminoisoindoline compound (II) with the aminoquinoline (III) takes place in anhydrous solvents at elevated Temperature. As a rule, temperatures between 50 ° C and 140 ° C. As a solvent, for. B. lower aliphatic carboxylic acids such as acetic acid or propionic acid can be used.

Die Menge an Lösungsmittel ist unkritisch und richtet sich danach, daß das Reaktionsgemisch durchmischbar ist. Die Farbstoffe der Formel (I) fallen in einer Form an, in der sie direkt zum Pigmentieren von Lacken, Druckfarben und besonders zum Färben thermoplastischer Kunststoffe verwendet werden können.The amount of solvent is not critical and depends on the fact that Reaction mixture is miscible. The dyes of formula (I) fall in a form in which they are used directly for pigmenting paints, printing inks and especially used for coloring thermoplastics can.

Die folgenden Beispiele sollen die Erfindung weiter erläutern. Die im folgenden genannten Teile und Prozentangaben beziehen sich auf das Gewicht.The following examples are intended to explain the invention further. The following The parts and percentages given relate to the weight.

Beispiel 1example 1

16 Teile 8-Aminochinaldin und 33 Teile 1-[Cyan-N-4′-chlorphenylcarbamoyl- methylen]-3-iminoisoindolin werden in 500 Teilen Eisessig 5 Stunden bei Siedetemperatur gerührt. Nach dem Abkühlen wird filtriert, mit Eisessig und Methanol gewaschen und getrocknet. Ausbeute: 40 Teile des Isoindolinfarbstoffes der Formel (IV) in Form eines rotstichig gelben Pulvers, das bei 280-285°C schmilzt. 16 parts of 8-amino quinaldine and 33 parts of 1- [cyano-N-4'-chlorophenylcarbamoylmethylene] -3-iminoisoindoline are stirred in 500 parts of glacial acetic acid at the boiling point for 5 hours. After cooling, it is filtered, washed with glacial acetic acid and methanol and dried. Yield: 40 parts of the isoindoline dye of the formula (IV) in the form of a reddish yellow powder that melts at 280-285 ° C.

Eingearbeitet in Polystyrol ergibt der Farbstoff (IV) klare rotstichig gelbe Färbungen mit guten Echtheiten.Incorporated in polystyrene, the dye (IV) gives a clear reddish tinge yellow colors with good fastness properties.

Beispiele 2 bis 21Examples 2 to 21

Man verfährt wie in Beispiel 1, verwendet jedoch als 1-[Cyanmethylen]-3- iminoisoindolin (II) und Aminochinolin (III) die in der folgenden Tabelle genannten. Man erhält Farbstoffe der Formel (I), die Färbungen in den angegebenen Farbtönen geben und die ähnliche Eigenschaften aufweisen wie die mit dem Farbstoff des Beispiels 1 erhaltenen Färbungen. The procedure is as in Example 1, but the 1- [cyanomethylene] -3- iminoisoindoline (II) and aminoquinoline (III) used are those mentioned in the table below. Dyestuffs of the formula (I) are obtained which give colorations in the specified shades and have properties similar to those obtained with the dye of Example 1.

Claims (5)

1. Isoindolinfarbstoffe der Formel in der R Cyan, C1- bis C4-Alkoxycarbonyl, Phenoxycarbonyl, N-C1- bis C4-Alkylcarbamoyl, N-Phenylcarbamoyl, Chinazolonyl-2, Chinoxalinonyl-2, Benzimidazolyl-2 oder Benzthiazolyl-2 bedeuten und der Ring A, das Chinolinringsystem, die Phenylringe in R und die Benzringe in den heterocyclischen Resten in R gegebenenfalls durch nichtlöslich machende Gruppen substituiert sind.1. Isoindoline dyes of the formula in which R is cyan, C 1 - to C 4 -alkoxycarbonyl, phenoxycarbonyl, NC 1 - to C 4 -alkylcarbamoyl, N-phenylcarbamoyl, quinazolonyl-2, quinoxalinonyl-2, benzimidazolyl-2 or benzthiazolyl-2 and the ring A, the quinoline ring system, the phenyl rings in R and the benz rings in the heterocyclic radicals in R are optionally substituted by non-solubilizing groups. 2. Isoindolinfarbstoffe gemäß Anspruch 1, dadurch gekennzeichnet, daß der Chinolinrest unsubstituiert oder in 3-Stellung durch Hydroxy oder in 4- Stellung durch Methyl substituiert ist und der Ring A unsubstituiert ist.2. Isoindoline dyes according to claim 1, characterized in that the Quinoline residue unsubstituted or in the 3-position by hydroxy or in 4- Position is substituted by methyl and the ring A is unsubstituted is. 3. Isoindolinfarbstoffe gemäß Anspruch 2, dadurch gekennzeichnet, daß R gegebenenfalls durch nicht löslichmachende Gruppen substituiertes N- Phenylcarbamoyl bedeutet.3. Isoindoline dyes according to claim 2, characterized in that R N- optionally substituted by non-solubilizing groups Phenylcarbamoyl means. 4. Isoindolinfarbstoffe gemäß Anspruch 3, dadurch gekennzeichnet, daß R für durch Methyl, Ethyl, Methoxy, Ethoxy, Methoxycarbonyl, Ethoxycarbonyl, Trifluormethyl, Fluor, Chlor oder Brom einfach substituiertes N- Phenylcarbamoyl steht.4. isoindoline dyes according to claim 3, characterized in that R for by methyl, ethyl, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, Trifluoromethyl, fluorine, chlorine or bromine monosubstituted N- Phenylcarbamoyl stands. 5. Verwendung der Farbstoffe gemäß den Ansprüchen 1 bis 4 zum Färben von Kunststoffen in der Masse.5. Use of the dyes according to claims 1 to 4 for dyeing Plastics in bulk.
DE19853533545 1985-09-20 1985-09-20 Isoindoline dyes Withdrawn DE3533545A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DE19853533545 DE3533545A1 (en) 1985-09-20 1985-09-20 Isoindoline dyes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19853533545 DE3533545A1 (en) 1985-09-20 1985-09-20 Isoindoline dyes

Publications (1)

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DE3533545A1 true DE3533545A1 (en) 1987-05-27

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5028708A (en) * 1987-04-14 1991-07-02 Sumitomo Chemical Company, Limited Azamethinyl quinoline derivatives
EP0742217A1 (en) * 1995-05-08 1996-11-13 Hoechst Aktiengesellschaft Isoindoline pigments based on aminoquinoxalindiones

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5028708A (en) * 1987-04-14 1991-07-02 Sumitomo Chemical Company, Limited Azamethinyl quinoline derivatives
US5061796A (en) * 1987-04-14 1991-10-29 Sumitomo Chemical Company, Ltd. Azamethine compounds
EP0742217A1 (en) * 1995-05-08 1996-11-13 Hoechst Aktiengesellschaft Isoindoline pigments based on aminoquinoxalindiones
US5716446A (en) * 1995-05-08 1998-02-10 Hoechst Aktiengesellschaft Isoindoline pigments based on aminoquinoxalinediones

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