GB378476A - Improvements in processes for the manufacture and production of vat dyestuffs and the dyestuffs produced thereby - Google Patents

Abstract

Fluoranthene derivatives.--Vat dyes are obtained by condensing fluoranthene (to which a recent structural formula is assigned) with anhydrides of aromatic o-dicarboxylic acids, such as phthalic anhydride, anthraquinone-1 : 2-dicarboxylic anhydride, naphthalene-2 : 3-dicarboxylic anhydride; halogenated phthalic anhydrides may be used instead of phthalic anhydride itself. The condensation may take place by heating the constituents alone or in the presence of condensing agents, such as aluminium chloride, sodium-aluminium chloride, antimony trichloride, ferric chloride, titanium tetrachloride, and in the presence of a solvent or diluent such as nitrobenzene. The products may be further modified by chlorination, bromination, nitration, amidation or by the introduction of an aroylamino group. Amidation is effected either by the reduction of nitro derivatives or by the condensation of the halogen derivatives with an aminoanthraquinone. An aroylamino group is introduced by aroylating an amino derivative. In examples (1) fluoranthene is condensed with phthalic anhydride in presence of sodium-aluminium chloride, or in trichlorbenzene and in presence of aluminium chloride, or in nitrobenzene and in presence of aluminium chloride; the product can be purified by treatment with solutions of caustic alkalis, alkali carbonates, or hypochlorites, and then by fractional precipitation from sulphuric acid solution, and dyes cotton greenish-yellow shades from the vat; (2) fluoranthene is condensed with naphthalene-2 : 3-dicarboxylic anhydride in nitrobenzene and in presence of aluminium chloride; the product dyes greenish-yellow shades; (3) fluoranthene is condensed with 4-bromophthalic anhydride in nitrobenzene and in presence of aluminium chloride to give a 2-bromophthaloylfluoranthene which dyes reddish-yellow shades; (4) fluoranthene is condensed with 4 : 5-dichlorphthalic anhydride in nitrobenzene and in presence of aluminium chloride; the product dyes reddish-yellow shades; (5) the phthaloylfluoranthene of (1) above is treated in nitrobenzene and in presence of iodine with sulphuryl chloride (dyes greenish-yellow shades), and with bromine (dyes greenish-yellow); (6) the 2-bromophthaloylfluoranthene of (3) above is condensed with a -aminoanthraquinone in nitrobenzene and in presence of cuprous chloride and sodium acetate; the product dyes reddish-brown shades; (7) the bromophthaloylfluoranthene of (5) above is similarly condensed with a -aminoanthraquinone to give a product dyeing corinth shades; (8) the bromophthaloylfluoranthene of (5) above is similarly condensed with leuco-1.4-diaminoanthraquinone to give a product dyeing grey to black shades.