Naphthoquinone series — Part I
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Brazanquinone vat dyes have been prepared by the condensation of 2∶3-dichloro-1∶4-naphthoquinone (I) with α- and β-naphthols and their bromo derivatives and by the condensation with Naphtol AS. Reaction of 1-bromo-2-naphthol with (I) in pyridine gave a halogenonaphthoquinone together with a halogen-free naphthoquinone which proved to be identical with the reaction product (A) obtained from (I) and β-naphthol in pyridine. The 1-position in β-naphthol is thus involved in the condensation with (I) and (A) is therefore constituted as the furan derivative, 1∶2-benzobrazanquinone (V). Constitution of “iso-dinaphthalene oxide” as dinaphtho-(2′∶3′∶2∶3-) (1″∶2″∶4∶5) furan (VI) (follows from its conversion to (V) by oxidation and conversely by its synthesis from (V) by zinc dust distillation. The condensation product of (I) with Naphtol AS is likewise the furan derivative 1∶2-brazanquinone-4-carboxyanilide (VIII) since it is also formed from 1-bromo-2-hydroxy-3-naphthanilide by loss of bromine.
Introduction of bromine in (V) and 3∶4-benzobrazanquinone and the introduction of the carboxyanilide group in (V) leads to more substantive dyes. The dyes give yellow and orange yellow shades. Fastness properties of the dyes have been determined.
KeywordsBetaine Naphthoquinone Fastness Property Sodium Ethoxide Furan Derivative
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