Phthalocyanine Dyes

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Phthalocyanine Dyes

 

(or phthalocyanine pigments), a group of dyes, derivatives of tetrabenzotetraazoporphyrin (phthalocyanine) and its complex compounds with metals. The most widely used phthalocyanine dye is copper phthalocyanine (I), a blue pigment.

The polymorphism of phthalocyanine dyes is important for their use: for example, (I) has α-, β-, and γ-modifications, which differ substantially in color and stability in organic solvents.

Copper phthalocyanine (I) is obtained by heating phthalic anhydride with urea, cuprous chloride (CuCl), and a catalyst, such as As2O5, at 160°–200°C in a medium of trichlorobenzene or nitrobenzene. It is also obtained by heating phthalonitrile, C6H4(CN)2, with CuCl, in which case a partially chlorinated light-blue pigment is formed. To obtain the α- and γ-forms, (I) is dissolved and reprecipitated from 98-percent and 60-percent sulfuric acid, respectively; preparation of the β-form involves the mechanical grinding of (I) in the presence of organic solvents and sodium chloride or sodium sulfate.

Phthalocyanine dyes containing 14–16 chlorine atoms in the benzene residue (bright-green pigment) are prepared by the chlorination of (I). Water-soluble direct phthalocyanine dyes are obtained by the sulfonation of (I).

Turquoise-colored reactive dyes are synthesized by the action of chlorosulfonic acid and thionyl chloride on (I), followed by the conversion of the tetrasulfochloride obtained to sulfamide by interaction with aromatic amines containing active groups. Water-soluble phthalocyanine dyes, called Alcians, are isothiouronic salts of (I) and contain one to three of the following group:

They are prepared by first subjecting (I) to the action of paraformaldehyde and hydrochloric acid and then to the action of tetramethyl thiourea; when applied to fabric these phthalocyanine dyes, after steam treatment, form a pigment in the pores of the fiber. Another method of obtaining phthalocyanine dyes during the dyeing process is by the interaction of l-amino-3-iminoisoindoline [phthalocyanogen, or phthalogen (II)] with copper salts in the presence of organic solvents; a fast pigment is formed on heating the fabric impregnated with this mixture to 120°–150°C.

Phthalocyanine dyes that are not water-soluble are widely used as pigments in the manufacture of printing colors, plastics, resins. and other products. Water-soluble phthalocyanine dyes (direct, active, sulfur, or other types) are used for dyeing fabrics.

The central fragments of phthalocyanine dyes and biological pigments—hemoglobin and chlorophyll—have similar structures.

REFERENCE

Chekalin, M. A., B. V. Passet, and B. A. Ioffe. Tekhnologiia organicheskikh krasitelei i promezhutochnykh produktov. [Leningrad] 1972.

M. A. CHEKALIN

References in periodicals archive ?
As the concentration of zinc(II) phthalocyanine 1b was increased, the intensity of the Q bands increased and any red or blue shift were not observed due to the aggregated species [21].
Types of pigments: Blacks (carbon black), Blues (basic dye pigments, phthalocyanine, indanthrone, quinacridone, PMA, PTA, methyl, tungstated), Greens (phthalocyanine, PMA, PTA), Reds (toluidine, naphthol, anthanthrone, DPP, manganese 2B, bon maroon, lithol rubine, antrhaquinone, quinacridone, alizarin, lithol rubine, perylene, rhodamine, robine red, AZO complex, bisacetoacetarylide), Yellows and Oranges (mono azo, diarylide, benzimidazolone, dispersion, bismuth vanadate, proprietary, dianisidine, dinitroaniline, hansa, isoindolinone, isoindoline, quinophthalone, naphthol, bisacetoacetarylide)
The Karawang Plant's key advantage is its integrated production capabilities, which encompass everything from phthalocyanine crude (pigment intermediates) for its own use to pigments for sale to customers.
Magnetoliposomes (MLs) loaded with zinc phthalocyanine (ZnPc)/cucurbituril (CB) complexes (CB:ZnPc-MLs) were synthesized for TPDT and magnetohyperthermia in malignant melanoma cells.
BaTi[O.sub.3]@Si[O.sub.2]@HBCuPc was obtained by reaction between hyperbranched copper phthalocyanine (HBCuPc) and BaTi[O.sub.3]@Si[O.sub.2] which were prepared through surface modification of BaTi[O.sub.3] with silane coupling agent KH550.
Optical and electrochemical measurements are in agreement with ab initio results based on density functional theory (DFT) [20] and are compared to simulations of Spiro-OMeTAD and tetra-tert-butyl zinc phthalocyanine (hereinafter referred to as [(t-Bu).sub.4]ZnPc) properties, chosen as internal standards.
Macrocyclic chemistry of phthalocyanine has attracted much interest because of its chemical properties and use in different areas (Figure 4).
Basova et al., "Chemical reaction of polar phthalocyanines on silver: chloroaluminum phthalocyanine and fluoroaluminum phthalocyanine," Journal of Physical Chemistry C, vol.
Synthesis of phthalonitriles from DCP shown a great potential to synthetize new phthalocyanines. The main goal was achieved in the third step of DCP synthesis, what took few minutes, with good yields, compared with hours in another published method.
Organic copper phthalocyanine blue pigment (2%-3% w/w of monomer) was introduced into styrene, and agitated by a magnetic stirrer at 400 rpm for half an hour.
phthalocyanine compound can be improved by chemical treatment with low solubility solvents [7].