Copper phthalocyanine structure

There is an interesting technique which makes it possible to introduce carboxylic acid groups into a copper phthalocyanine structure by an economical route. Carrying out the phthalic anhydride/urea process in the presence of a small amount of trimellitic acid or another benzene polycarboxylic acid will afford a car-boxylated pigment. 

Flocculation may likewise be prevented through partial introduction of dialkyl-aminomethylene groups into the aromatic ring system of the copper phthalocyanine molecule. The copper phthalocyanine structure tightly attaches the basic groups... 

Copper(II), di-/Lt-bromobis[bromo(pyridine)-structure, 2, 108 Copper 8-hydroxyquinolinate biocidal activity mechanism, 1, 401 fungicide, 1, 399 Copper nitrotetrazole as propellants, 5, 837 Copper phthalocyanine, 1, 333-334 colour and constitution, 1, 345 Coproporphyrin, 4, 382 Coproporphyrin, dehydro-, 4, 382... 

Polyphosphazene-Phthalocyanlne Structures. Thus, a related study was carried out with copper phthalocyanine units linked covalently to a poly(aryloxyphosphazene) (44). Non-polymeric copper phthalocyanine forms ordered stacked structures in the crystalline state. When... 

Copper Phthalocyanine Blue is the copper(II) complex of tetraazatetrabenzo-porphine. As shown below, the mesomeric structures indicate that all of the pyrrole rings simultaneously contribute to the aromatic system ... 

In 1929, Linsted obtained samples of this complex from ICI chemists (Scottish Dyes Ltd was now owned by ICI). ICI had developed two routes leading to the phthalocyanine iron complex. One method started from phthalic anhydride, iron, and ammonia, while the second pathway proceeded from phthalimide, iron sulfide, and ammonia. In 1933/34, elucidation of the phthalocyanine structure was credited to Linstead. The corresponding copper and nickel phthalocyanines had been prepared in the meantime. ICI introduced the first Copper Phthalocyanine Blue to the market as early as 1935, and the Ludwigshafen subsidiary of the IG Farben-industrie followed suit with a corresponding product. 

Moreover, the phthalonitrile process has the added advantage of being the more elegant of the two syntheses. This technique makes it possible to produce comparatively pure copper phthalocyanine without obtaining substantial amounts of side products, a phenomenon which is understandable in view of the fact that the phthalonitrile molecule provides the parent structure of the phthalocyanine ring. Formally, rearrangement of the bonds necessitates donation of two electrons to the system ... 

Urea acts not only as an ammonia source but also forms decomposition products, such as biuret and higher condensation products. 14C labeling has indicated that the carbon atom of the urea molecule is not incorporated into the phthalocyanine structure. Employing a phthalic anhydride molecule bearing one radioac-tively labeled carbonyl function affords labeled copper phthalocyanine and phthalimide (as a side product), while the liberated carbon dioxide was found not to show any radioactivity. Labeled carbon dioxide, on the other hand, has been obtained in corresponding experiments using 14C labeled urea. 

Recently, by crystal structure studies the number of different polymorphs of Copper Phthalocyanine Blue has been extended to nine, various of which are differing mainly in herringbone-type interaction [17]. 

Three dimensional X-ray diffraction analysis has been employed to elucidate the molecular and crystal structure of Copper Phthalocyanine Blue ((3-modifica-tion). In all modifications, the planar and almost square phthalocyanine molecules are arranged like rolls of coins, i.e., in one dimensional stacks. The modifications vary only in terms of how these stacks are arranged relative to each other. One important aspect is the angle between staple axis and molecular plane. The a-phase features an angle of 24.7°, while the stacks in the -modification deviate by as much as 45.8° [13]. 

Fig. 92 Arrangement of the CuPc molecules of the a- and the p-modification. The data for the ot-modification relate to the structure of 4-mono-chloro copper phthalocyanine, which is isomorphous with ot-CuPc [13].

Introducing suitable substituents into the Copper Phthalocyanine Blue structure or covering the crystal surface with appropriate substances may specifically influence the hydrophilicity or the polarity of the pigment (Sec. 3.1.2.4). The ease of dispersion and wetting may thus be improved or optimized for certain applications, such as for aqueous media. 

Figure 2 Molecular structure of copper phthalocyanine (CuPc)...

The relationship between fs and zlEphot holds only for dyes of similar chemical structure, so that e.g. there is no connection between A phot and ( of copper-phthalocyanine. 

---