Patent GB-358074-A (GB)
Title: The manufacture of nitrogenous vat dyestuffs
IPC: C09B5/40
Filed: 1930-05-31
Abstract: Benzanthrone derivatives.-Vat dyes are obtained by treating with an alkaline condensing agent at 1-(Bz1-benzanthronylamino)-anthraquinone containing in the 4-, 5-, or 8-position of the anthraquinone nucleus an alkylamino-, cycloalkylamino-, aralkylamino-, arylamino-, dialkylamino-, or alkyl-aralkylamino-group, but not containing more than one anthraquinone radicle directly bound by an imino group to the benzanthronyl residue.  The products dye grey shades which differ from the dyestuffs of Specification 24604/08, [Class 2, Acids and salts, Organic &c.], which do not contain a substituted or unsubstituted amino group in the 4-, 5-, or 8-position of the anthraquinone nucleus.  Compared with the corresponding products containing an unsubstituted amino group the dyestuffs possess better fastness to chlorine, and better capacity for vatting.  The products containing the substituted amino groups intact may be further treated with acid condensing agents.  The use of sulphuric acid, chlorsulphonic acid or the like in this connection increases the solubility of the dyestuffs in the vat and hence their levelling power, probably on account of sulphonation taking place; the use of a sodium-aluminium chloride melt results in products dyeing brownish shades from those dyestuffs containing an arylamino group.  The treatment of the following products with alcoholic caustic potash is described in examples, structural formul  being assigned to each of the resulting products: (1) 1-(Bz1-benzanthronylamino) - 5 - butylaminoanthraquinone; the product dyes grey-blue shades, its levelling power being increased by treatment with sulphuric acid: (2) 1-(Bz1-benzanthronylamino)-5-b -ethanolaminoanthraquinone; the product dyes bluish-grey shades: (3) 1-(Bz1-benzanthronylamino)-4- or 5-or 8-cyclohexylaminoanthraquinone; the products dye olive-grey, blue-grey, and green-grey shades and the levelling power of the last two products is improved by an after-treatment with sulphuric acid: (4) 1-(Bz1-benzanthronylamino)-5-benzylaminoanthraquinone; the product dyes grey shades: (5) 1-(Bz1-benzanthronylamino)-4-anilidoanthraquinone, the product dyes olive-grey shades, and, after treatment with sodium-aluminium chloride, dyes brown shades: (6) 1-(Bz1-benzanthronylamino)-5-p-tolylaminoanthraquinone; the product dyes greyish-blue shades: (7) 5-(Bz1-benzanthronylamino)-1.11-anthrimide (which is a feeble vat-dye); the product dyes grey, changed to bluish-grey by after-treating the product with chlorsulphonic acid, and to olive by after-treating the product with sodium-aluminium chloride: (8) 5-(Bz1-benzanthronylamino)-1.21-anthrimide; the product dyes reddish-grey shades which become more bluish-grey if the product is aftertreated with an acid agent: (9) 5-(Bz1-benzanthronylamino)-51-hydroxy - 1.11 - anthrimide; the product dyes reddish grey-black shades; similar dyestuffs are obtained from 4- or 8-(Bz1-benzanthronylamino)-1.11- or 1.21-anthrimide: (10) 1-(Bz1-benzanthronylamino)-5-dimethylaminoanthraquinone; the product dyes greyish-blue and its levelling power is improved by treatment with sulphuric acid; from 1-(Bz1-benzanthronylamino)-5-diethylamino- and 5-ethylbenzylaminoanthraquinone similar dyes are obtained.  The starting materials for the process are prepared by condensing Bz1-brombenzanthrone with a 1-aminoanthraquinone containing in the 4-, 5-, or 8-position an alkylamino, cycloalkylamino and &c. group; in some cases the substances are prepared by condensing together a Bz1-brombenzanthrone, the alkylamine, cycloalkylamine and &c., and the 1-amino-4-, 5-, or 8-halogenanthraquinone in molecular proportions.  Aminoanthraquinones required as intermediate starting materials in the above examples are prepared by the customary methods.  Thus 1-amino-5-butylaminoanthraquinone, 1-amino-5-b -ethanolaminoanthraquinone and 1-amino-4-, 5-, or 8-cyclohexylaminoanthraquinones are prepared from the corresponding 1-amino-halogenanthraquinone by condensation with the appropriate amine.  1-Amino-5-ethylbenzylaminoanthraquinone is obtained by reacting ethylbenzylamine with 1-benzoylamino-5-chloranthraquinone and saponifying the product.