hydroxyl group. If, for instance, the liquid containing the product of the reaction (in case an excess of anhydrid has been used a corresponding excess of alkali is added, so that at the end of the acetylization all may be completely dissolved and the reaction to red litmus may be even feebly alkaline) is mixed with mineral acid and nitrite while cooling with ice until even after lengthy waiting iodin paper still shows a reaction, there is obtained a diazo compound which separates as yellow crystals and may be easily coupled with azo dyestuff components. From its behavior it appears to be ortho-acetoxydiazonaphthionic acid. It combines, for example, with beta-naphthol to form a red dyestuff which gradually or more quickly when warmed passes to a greenish-blue dyestuff in consequence of the elimination of the acetyl group. This elimination occurs also when the said diazo compound is allowed to remain long at rest. Already after the lapse of an hour it is found that a sample treated with an alkaline solution of beta-naphthol does not combine immediately and with a red color, but more gradually with a yellowish-green and later a blue color, a behavior which must be ascribed to the diazonaphtholsulphonic acid which indeed is characterized by great stability toward heat, however, differs by the more gradual coupling tendency from the corresponding acetyl derivative. The diazonaphtholsulphonic acid is somewhat sparingly soluble in water containing mineral salts, but more easily soluble in pure water.

BLACK AZO DYE.

Martin Herzberg, of Elberfeld, Germany, assignor to Farbenfabriken of Elberfeld Co., of New York, N. Y. Patent No. 797,731, dated August 22, 1905.

The inventor has found that new and valuable azo dyestuffs are obtained by first combining the diazo compounds obtainable from mononitroacetyl-paraphenylenediamin having the formula

with alkyloxynaphthol disulphonic acid and then splitting off from the resulting dyestuffs the acetyl group by saponification.

The new dyestuffs are in the shape of their alkaline salts dark powders soluble in water. They yield upon suitable treatment with stannous chlorid and hydrochloric acid triamidobenzene and amidoalkyloxynaphthol disulphonic acids and dye unmordanted wool from acid-baths black shades.

BLACK AZO DYE.

Martin Herzberg, of Elberfeld, Germany, assignor to Farbenfabriken of Elberfeld Co., of New York, N. Y. Patent No. 797,732, dated August 22, 1905.

It is found that new and valuable azo dyestuffs are obtained by first combining the diazo compounds obtainable from mononitroacetyl-paraphenylenediamin having the formula

with alkylamidonaphthol disulphonic acids, and then splitting off from the resulting dyestuffs the acetyl group by saponification. By the term "alkylamidonaphthol disulphonic acids" are meant amidonaphthol disulphonic acids which are substituted in the amido group by alkyls or aryls, such as methyl, phenyl, benzyl, dinitrophenyl, the glycin group, or the like.

The new dyestuffs are in the shape of their alkaline salts dark powders soluble in water. Iney yield upon suitable reduction with stannous chlorid and hydrochloric acid triamidobenzene and amidoalkylamidonaphthol disulphonic acids. They dye unmordanted wool from acid-baths black shades.

YELLOWISH AZO DYE.

Fritz Carl Günther, of Ludwigshafen-on-the-Rhine, Germany, assignor to Badische Anilin und Soda Fabrik. Patent No. 798,098, dated August 29, 1905.

The inventor has discovered that by combining 2.6-diamido-1chlor-benzene-4-sulpho-acid with diazo compounds of the benzene and naphthalene groups new and valuable coloring-matters can be obtained which dye wool from an acid-bath, yielding from pure yellow to reddish-yellow shades which have a bright appearance "overhand" and are also very fast against the action of acids, the said coloring-matters possessing excellent equalizing power. The diazo compounds found to yield especially valuable coloring-matters when combined with 2.6-diamido-1-chlor-benzene4-sulpho-acid include the diazo compounds of sulphanilic acid, metanilic acid, meta-nitranilin, naphthionic acid, anilin, and 2.1naphthylamin sulpho-acid.

The coloring-matters which claimed generically are those which can be obtained by combining a diazo compound of the benzene or naphthalene groups with 2.6-diamido-1-chlor-benzene-sulpho-acid, and they possess the following properties: They dissolve in water, and the solutions, to which a little sodium carbonate has been added, are from reddish yellow to greenish yellow. When dyed on wool, they produce from reddish-yellow to greenish-yellow shades. Upon reduction with tin and hydrochloric acid they yield 2.3.6-triamido-1-chlor-benzene-4-sulpho-acid.

The coloring-matter which claimed specifically is that which can be obtained by combining diazotized sulfanilic acid with 2.6-diamido-1-chlor-benzene-4-sulpho-acid.

ANTHRACENE COMPOUND AND PROCESS OF MAKING SAME.

Max Henry Isler, of Mannheim, Germany, assignor to Badische Anilin und Soda Fabrik. Patent No. 798,104, dated August 29, 1905.

In the specification of U. S. Patent No. 787,859, is described the production of new products of the anthracene series by condensing certain anthracene compounds with glycerin. These anthracene compounds include anthracene itself, also anthraquinone, anthranol, oxanthranol, and the sulpho-acids of these compounds, and in

all cases the new condensation products contain a benzanthrone grouping. It is now discovered that similar new compounds which fall generically under the claims of the above-mentioned specification, but which are specifically different, can be obtained by condensing a naphthanthraquinone body with glycerin. The bodies of use in this invention include naphthanthraquinone itself, also its homologues and the hydro derivatives of all these compounds. The condensation proceeds in a manner very similar to that described, and bodies containing the benzanthrone group, although, of course, with another benzene ring attached, are obtained. These can conveniently be termed specifically "benznaphthanthrones and they possess the following properties: They are insoluble in water, but are soluble in concentrated sulphuric acid. On being melted with caustic alkali they yield dyestuffs which, similarly to those obtained from the products claimed in the above-mentioned specification, can be dyed from alkalinehydrosulphite vat. They produce shades, however, which are more greenish blue.

دو

DIAMIDODIPHENYLAMIN SULPHONIC ACID AND PROCESS OF MAKING SAME.

Hugo Geldermann, of Berlin, Germany, assignor to Actiengesellschaft für Anilin Fabrikation. Patent No. 800,735, dated October 3, 1905.

The inventor has found that new diamidodiphenylamin sulphonic acids, which are of very great value for dyeing purposes, can be produced by reducing the corresponding nitroamidodiphenylamin sulphonic acid obtained by the action of para-chlornitrobenzene sulphonic acid:

on a meta-diamin of the benzene series, such as meta-phenylenediamin or metatoluylenediamin. These bodies are an excellent means

for dyeing leather in so far as they permit of a thorough penetration of the leather if black tints are to be produced therewith. In doing so these substances are to be used in combination with an oxidizing agent.

YELLOW-RED AZO DYE.

Wilhelm Herzberg, of Berlin, Germany, assignor to Actien Gesellschaft für Anilin Fabrikation. Patent No. 800,914, dated October 3, 1905.

This invention relates to the production of a new group of mono-azo coloring-matters which in the form of their lakes are distinguished by their brilliant blue-red or yellow-red shade and by a great fastness against the action of light, which lakes are insoluble in water and oil.

These new azo dyes are derived from an ortho-amido-sulfonic acid of the benzene or naphthalene series the diazo compounds of which is combined in the usual manner with 2.7-diovynaphthalene, the azo dyes thus obtained is treated, for instance, with benzenewhich is combined in the usual manner with 2.7-dioxynaphthalene, sulpho chlorid CH ̧.SO2.Cl or para-toluene-sulpho chlorid CH¿C ̧H.SO2.Cl in the presence of an alkaline agent. Thus the general

X meaning the radical of an ortho-amido sulphonic acid of the benzene or naphthalene series-as, for instance, para-nitranilinortho-sulphonic acid, meta-chloro-anilin-ortho-sulphonic acid, paratoluidin-ortho-sulphonic acid, para-phenetidin-ortho-sulphonic acid, 2.1-naphthylamin-ortho-sulfonic acid, etc., and R meaning the radical C.H, or CH.CH, or another suitable sulphonic acid, the chlorid of which is to act on the one OH group of the 2.7-dioxynaphthalene, yielding the corresponding ester.