Patent GB-492043-A (GB)
Title: Improvements in the manufacture and production of vat dyestuffs
Filed: 1937-03-15
Abstract: Vat dyestuffs are manufactured by treating derivatives of peri-naphthindenones, having in the 7-position or in the 6- and 7-positions either hydrogen or a substituent easily split off, viz. a halogen atom or a nitro group, with alkaline agents, and oxidizing any amounts of dyestuff which are in the leuco form. Suitable starting materials are peri-naphthindenones having two free peri-positions and containing in the other positions of the molecule halogen atoms and/or alkyl, alkoxy, carboxyl or amino groups, or peri-naphthendenones containing in the 6- or 7-position halogen atoms or nitro groups and, if desired, any further of the said substituents, or containing in the 6-position a cyclic radicle, combined by a nitrogen bridge which may be part of a ring attached to the cyclic radicle, incapable of being split off and having a free o-position, e.g. radicles of a -aminoanthraquinones, a -aminoanthrapyrimidines, 1 : 9-pyrazolanthrones having a free 2-position, a -aminoazabenzanthrones, a -aminoazanthraquinones, a -aminopyridinoanthraquinones or a -aminobenzanthraquinones, and containing hydrogen or a substituent easily split off in the other periposition, and, if desired, containing any further of the said substituents.  The reaction is preferably effected by heating the initial materials, if desired with the addition of diluents such as aliphatic alcohols, with alkali metal hydroxides.  The products dye vegetable and animal fibres.  In examples: (1) 2-chloro-peri-naphthindenone is heated with alcoholic caustic potash; the product dyes cotton violet shades from a pale red vat; (2) 2-amino- or 2-dimethylamino-peri-naphthindenone is similarly treated; the products dye cotton grey and violet shades respectively from pale red vats; (3) 2-(11-or 21-anthraquinonylamino) - peri - naphthindenone (obtainable by reacting 1- and 2-aminoanthraquinone respectively with 2-bromoperi-naphthindenone), 2-pyrazolanthronyl-perinaphthindenone (obtainable by reacting 1 : 9-pyrazolanthrone with 2-bromo-peri-naphthindenone) or 2-(51-anthrapyrimidylamino)-perinaphthindenone (obtainable by reacting 5-aminoanthrapyrimidine with 2-bromo-peri-naphthindenone) is similarly treated; the products yield olive-green, grey, yellow-red and violet-grey dyeings respectively; (4) 2 : 6-di-(11-anthraquinonylamino) - peri - naphthindenone or 2 : 6-dipyrazolanthronyl - peri - naphthindenone (obtainable by reacting 2 molecular proportions of 1-aminoanthraquinone or 1 : 9-pyrazolanthrone respectively with one of 2 : 6-dibromo-peri-naphthindenone, obtained by brominating 2 - bromo - peri - naphthindenone) is similarly treated; the products dye cotton olive-green and yellow-brown shades respectively; (5) 2-(11-anthraquinonylamino)-6-pyrazolanthronyl - peri - naphthindenone (obtainable by reacting 2-chloro-6-bromo-peri-naphthindenone, obtained by brominating 2-chloroperi - naphthindenone, with 1 : 2-pyrazolanthrone and then with 1-aminoanthraquinone) is similarly treated; the product dyes vegetable fibres violet-grey shades from a grey vat; (6) benzoyl-peri-naphthindenone (obtained by reacting peri-naphthindenone with benzoyl chloride in the presence of pyridine) is heated with a solution of caustic potash in methanol; the product dyes vegetable fibres yellow shades from a pale red vat; (7) 2-chloro - 6 - (11 : anthraquinonylamino) - perinaphthindenone (obtainable by reacting 1-aminoanthraquinone with an equimolecular proportion of 2-chloro-6-bromo-peri-naphthindenone), 2 - benzoylamino - 6 - (11 - anthraquinonylamino) - peri - naphthindenone (obtainable by reacting 2-benzoylamino-6-bromo-peri-naphthindenone with 1-aminoanthraquinone) or 2 - chloro - 6 - N - pyrazolanthronyl-peri - naphthindenone (obtainable by reacting 2 - chloro - 6 - bromo - peri - naphthindenone with the potassium salt of 1 : 9 - pyracolanthrone) is similarly treated; the products dye vegetable fibres green, olive-green and blue shades respectively from violet vats.