Isoindolinone metal complexes

Methine isoindolinone metal complex pigments, in general, have so far met with very limited commercial success. This is primarily due to their dull and weak shades, as well as low fastness properties. 

Crystal PS Good light stability Processing temperatures up to 240°C Red and yellow toners Polycyclics Azo condensation Isoindolinone Metal complex Phthalocyanine Blue Phthalocyanine Green Selected dyes Ultramarine Blue Cadmium pigments Lead pigments Special monoazos... 

Yet another structural principle is represented by metal complex pigments based on isoindolinones. Condensation of amino-iminoisoindolinones (imino-phthalimide) with 2-aminobenzimidazole in a high boiling solvent affords an azomethine (36). This compound reacts with salts of divalent metals, such as Co, Cu, Ni, to yield yellow azomethine metal complex pigments [10] ... 

P.Y.179, an isoindolinone/cobalt complex pigment, was introduced to the market only few years ago but the production has recently been discontinued. It was recommended for use in paints, especially in automotive finishes. The pigment produces a reddish yellow shade. High lightfastness and excellent weatherfastness are an asset in pastel colors. Besides, good transparency made P.Y.179 a suitable product for metallic finishes. Yet, it is not quite as weatherfast as the equally reddish yellow P.Y.24, a flavanthrone pigment. 

The most important class of organic pigments in terms of production are the azo pigments. Other important pigment classes include metal-complex pigments (e.g., copper phthalocyanine) and higher polycyclic compounds (e.g., anthraquinone, quinacridone, isoindolinone, and perylene). 

Further, stable 2 1 transition metal complex pigments 27 (C.I. Pigment Yellow 177) and 28 (C.I. Pigment Yellow 179), featuring six-ring chelates, have been prepared from methine and azomethine type isoindolinones l... 

Metal complex pigments Isoindolinone and Isoindoline pigments... 

Impact PS Good light stability. Must withstand temperatures up to 280X Yellow and red toners Polycyclics Isoindolinone Selected Bis-arylamides Phthalocyanine Blue Phthalocyanine Green Metal complex Selected dyes Cadmium pigments Ultramarine Blue Azo condensation Special monoazos... 

The formation of ortho palladium products from a-aryl nitrogen derivatives and palladium salts is well known. Complexes formed from azobenzene, Schiff bases, tertiary benzylamines and oximes readily undergo insertion of CO into the metal-carbon bond to give, after work-up, a variety of heterocyclic compounds. Unfortunately, such reactions use expensive palladium salts in stoichiometric quantities. However, a number of related reactions have been shown to proceed in the presence of only catalytic quantities of palladium. Isoindolinones, for example, can be synthesized in good yield by reaction of o-bromoaminoalkylbenzenes with CO (100 C, 1 bar) in the presence of catalytic amounts of Pd(OAc)2, PPha and Bu"3N (equation 56). °... 

For example, meso-tetraaryltetrabenzoporphyrin zinc complex results from heat treatment of the corresponding 3-benzylidenisoindolinone with zinc benzoate l Appropriately substituted methine and azomethine isoindolinones featuring substructure 24 were also converted into stable metal chelate pigments of general structure 26 via a metal template reaction with aromatic and heterocyclic a-hydroxy aldehyde or ketone hydrazone derivatives incorporating the structural element 25 . ... 

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