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Quinacridone 6,13-disubstitution

There are also certain disubstituted quinacridones which are used commercially. The two peripheral rings in such quinacridone systems (53) are partially chlorinated or methylated. In the sequence 57 - 58 - 53 (p. 455), possible substitution sites on the peripheral rings are indicated by dashes (see also tables of chemical structures in the appendix). [Pg.457]

Table 18-1. Spectral Date for Quinacridone and some 2,9-disubstituted derivatives. Table 18-1. Spectral Date for Quinacridone and some 2,9-disubstituted derivatives.
Table 18-2. Relative solubility and photochemical stability of Quinacridone and some 4,11-disubstituted derivatives. Table 18-2. Relative solubility and photochemical stability of Quinacridone and some 4,11-disubstituted derivatives.
Similarly, quinacridone forms solid solutions with 2,9-dimethyl or 2,9-dichloroquina-cridone at about a ratio of two moles of unsubstituted to one mole of the substituted compound, the X-ray diffraction patterns of which are virtually identical and are different from those of mixtures of the individual ingredients (Figure 18-13). One blue-shade red is an article of commerce (P.V. 42, CAS 71819-79-9. In fact, using quinacridone and three 2,9-disubstituted derivatives, a series of binary and ternary solid solutions are formed, as depicted in Figure 18-14. The large triangle is subdivided into four smaller triangles and the areas where binary and ternary solutions are possible are shown. It is obvious that solid formation is unpredictable and requires numerous experimental determinations to delineate areas of solid solution formation. [Pg.297]

A specified mixture of aniline and one or more substituted anilines such as p-toluidine, p-chloro aniUne, and p-anisidine as examples is condensed with DMSS 7 to produce, after subsequent hydrolysis and oxidation of the resulting dihydrodiesters, a corresponding mixture of the diarylaminoterephthalic acids. An example using a para-substituted aniline is shown in Scheme 18.14. Cyclization of this mixture of terephthaUc acids in PPA followed by appropriate conditioning of the recovered crude product affords a ternary solid solution composed of quinacridone 2, 2-substituted quinacridone 27, and 2,9-disubstituted quinacridone 28. Several combinations are reported, providing a wide range of solid solutions and thus colors. [Pg.304]

Quinacridones substituted in the peripheral rings are synthesized by the methods described earlier by including appropriately substituted aniUnes. Anilines that are p- and o-substituted afford 2,9- and 4,11-disubstituted quinacridones, respectively. By contrast, the inclusion of m-substituted aniUnes afford intermediate terephtha-lic acids that possess two distinct sites that compete for cyclization, subsequently resulting in the formation of the three possible isomers 3,10-, 1,8- and 1,10-disub-stituted quinacridones. The 3,10-isomer predominates in the mixture because it is formed by cyclization at the least stericaUy hindered sites of the intermediate product. In some instances, the three isomers can be separated. The individual compounds also can be distinguished by inspection of the NMR spectra of the mixtures [36]. Like the parent compound, many of the substituted derivatives, including 6,13-dihydroquinacridone [37], exhibit polymorphism For example,... [Pg.311]

The colors of 4,11-disubstituted quinacridones, unlike the 2,9-disubstituted counterparts, are dominated by steric rather than electronic effects. As displayed in Table 18.2, the solubility of these compounds (boiling a-chloronaphthalene, b.p. 264 C) increases with increasing bulk of the substituents and correspondingly the photochemical stability in the solid state decreases. [Pg.312]


See other pages where Quinacridone 6,13-disubstitution is mentioned: [Pg.31]    [Pg.461]    [Pg.31]    [Pg.289]    [Pg.290]    [Pg.291]    [Pg.294]    [Pg.294]    [Pg.295]    [Pg.311]    [Pg.311]    [Pg.312]    [Pg.313]    [Pg.317]    [Pg.317]   
See also in sourсe #XX -- [ Pg.317 ]




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Other 6,13-Disubstituted Quinacridones

Quinacridones

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