ANTHRAQUINONE DYE.

Paul Thomaschewski, of Elberfeld, Germany, assignor to Farbenfabriken of Elberfeld Co., of New York, N. Y. Patent No. 801,418, dated October 10, 1905.

This invention relates to the manufacture of a new dyestuff, being a hydroazin derivative of the anthracene series.

The process for producing this coloring-matter consists in heating the 1-oxy-3-bromo-4-amidoanthraquinone (obtainable by the action of bromin on paraämido-oxyanthraquinone) with cupric chlorid in the presence of a suitable dissolving or diluting agent and preferably with the addition of a product having a weak alkaline reaction, such as sodium acetate or the like.

The new coloring-matter thus obtained crystallizes from quinolin the shape of blue needles having a cupreous lustre. It is soluble in hot quinolin with a bluish-green color and soluble in concentrated sulphuric acid with an olive-green color. Upon treatment with hydrosulphite and caustic-soda lye it is transformed into its hydro compound, the blue alkaline solution of which has the properties of a vat" suitable for dyeing and printing unmordanted cotton pure greenish-blue fast shades.

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BROWN SULPHUR DYE AND PROCESS OF MAKING SAME.

August Leopold Laska, of Offenbach-on-the-Main, Germany, assignor to the firm of K. Oehler, Anilin- und Anilinfarbenfabrik. Patent No. 801,598, dated October 10, 1905.

This invention relates to the manufacture of new brown sulfur dyes, which are distinguished by excellent properties of fastness. These dyestuffs are produced by subjecting to the melting process with alkali polysulphides the reaction products of formaldehyde and resorcin-as, for instance, methylene diresorcin or its condensation products-insoluble in alkalies, (cf. Caro, Ber. D. D. Chem. Ges., XXV., 947, and Möhlau, ibid, XXVII., 2888,) together with the metadiamins of the benzol series. The new dyestuffs represent

uniform products. They cannot be formed by mixing the dyestuffs, which might result by melting the single components.

GREEN-BLUE SULPHUR DYE AND PROCESS OF MAKING SAME.

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Ivan Levinstein and Ernest Eugene Naef, of Manchester, England. Patent No. 802,409, dated October 17, 1905.

The inventors have found that para-nitrosophenol and paranitroso-ortho-cresol or any of the two said compounds which contain a chlorin atom in the ortho position to the hydroxyl group condense under suitable conditions with amidosulpho acids of the benzene and naphthalene series, which have the para position to the amido group unoccupied forming blue-colored compounds. These substances or their reduction products yield, when heated with sodium polysulphides, most valuable new dyestuffs which dye unmordanted cotton greenish-blue shades fast to acid and light.

INDOPHENOL SULPHONIC ACIDS AND PROCESS OF MAKING SAME.

August Leopold Laska, of Offenbach-on-the-Main, Germany, assignor to the firm of K. Oehler, Anilin- und Anilinfarbenfabrik. Patent No. 798,807, dated September 5, 1905.

This invention relates to the production of new indophenol sulphonic acids, which are distinguished from other indophenol bodies by their fair stability. These new indophenol sulphonic acids can be obtaned by simultaneously oxidizing in an alkaline solution paraphenylendiamin sulphonic acid and a phenol. They represent very important initial materials in the manufacture of sulphur dyes.

BLUE AZO WOOL DYE AND PROCESS OF MAKING SAME.

August Leopold Laska, of Offenbach-on-the-Main, Germany, assignor to the firm of K. Oehler, Anilin und Anilinfarbenfabrik. Patent No. 798,808, dated September 5, 1905.

This invention relates to the production of a new dyestuff by combining the diazotized 6-nitro-2-amidophenol-4-sulphonic acid with betaoxynaphthoic acid of the fusing-point of 216° centigrade. The new dyestuff yields on wool, even when dyed in a proportion of only two per cent., an indigo blue which is of a particular value because of its greenish shade.

AZO-DYE LAKE AND PROCESS OF MAKING SAME.

Carl Immerheiser, of Ludwigshafen-on-the-Rhine, Germany, assignor to the Badische Anilin und Soda Fabrik. Patent No. 799,058, dated September 12, 1905.

The inventor has discovered that coloring-matter lakes can be prepared from such insoluble azo coloring-matters as shortly after their preparation have a soft, oily, or a resinous consistence or which at a temperature of about 100° centigrade are soft or liquid -that is to say, the coloring-matters must be readily fusible without decomposition.

As examples of azo coloring-matters which are suitable for the purposes of this invention are those prepared from crude xylidin and beta-naphthol (which at ordinary temperature when freshly turn xylidin—that is, the product resulting when crude xylidin has been freed as far as conveniently possible from meta xylidin and para xylidin, as is done in the manufacture of these bodies, and beta-naphthol, also crude or return, xylidin azo-cresol or azophenol, or ortho-toluidin azo-phenol or azo-para-cresol, and the like.

To prepare the new lakes, a coloring-matter of the character aforesaid—such, for instance, as that prepared from crude xylidin and eta-naphthol (which at ordinary temperature when freshly prepared is a pasty, oily or resinous mass) is warmed and intimately mixed with dry and finely ground heavy spar, kaolin, aluminina, or any other substratum usually employed, or capable of use for the preparation of lakes, or the substratum can be made into a paste and be intimately stirred with the melted coloringmatter. The paste so obtained can be directly employed, or it can

be dried at ordinary or a higher temperature. The ultimate shade is not fully developed until the lake is dry.

MONOAZO DYE AND PROCESS OF MAKING SAME.

Wilhelm Herzberg and Otto Siebert, of Berlin, Germany, assignors to Actien Gesellschaft für Anilin Fabrikation. Patent No. 803,592 dated November 7, 1905.

It is well known that mordant dyeing mono-azo dyestuffs are obtained by combining the diazo compound of ortho-amidophenol with phenols, amidophenols, amins, diamins, or the sulphonic or corboxylic acids thereof. Mordant dyeing coloring-matters of the same kind are also described in literature which contain in the benzol nucleus of the ortho-amido-phenol certain substitutes -as, for instance, chlorin, methylnitro, or sulpho group.

This invention relates to the manufacture of new azo dyestuffs of the following formula:

in which X represents hydrogen, chlorin, the sulphonic or carboxylic group, Y a naphthol compound, and R stands for hydrogen or an alkyl group, such as the methyl, ethyl group, &c.

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By naphthol compounds are understood besides naphthol itself, such derivatives thereof as contain a second hydroxyl group or a sulphonic group.

These dye wool from an acid-bath brown-red shades which are

changed to a deep black by a subsequent treatment with chromium compounds, acting as oxidizing agents.

CYANIN DYE AND PROCESS OF MAKING SAME.

Ernst König, of Höchst-on-the-Main, Germany, assignor to Farbwerke vorm. Meister, Lucius & Brüning. Patent No. 805,143, dated November 21, 1905.

The object of the present invention is to produce quinaldincyanins which will render the photographic plate more sensative to red than do those known. For this purpose a mixture of an alkyl halide of quinolin or of quinolin substituted in the meta or para position (which, according to another nomenclature, is the 5 or 6 position) by alkyl or alkyl oxyl and an alkyl halide of quinaldin similarly substituted or a mixture of an alkyl halide of quinoldin substituted in the meta or para position by alkyl or alkyloxyl and an alkyl halide of quinaldin is heated with alkali in a suitable solvent, such as alcohol.

The following dyestuffs have been made according to this inven tion: quinaldin meta toluquinolinalkyleyanin, quinaldin paratoluquinolinalkyleyanin, quinaldin-para-methoxy-quinolinalkyley

anin, meta-toluquinaldinquinolinalkylcyanin, meta-toluquinaldin

meta-toluquinolinalkyleyanin, meta-toluquinaldin-para-toluquino

linalkyleyanin, para-toluquinaldin-quinolinalkyleyanin, para-tolu

quinaldin-meta-toluquinolinalkyleyanin, para-toluquinaldin-para

toluquinolinalkyleyanin, para-toluquinaldin-paramethoxy-quinoli

nalkyleyanin, para-methoxyquinaldin-para-methoxyquinolincyanin,

para-ethoxyquinaldin-para-ethyoxyquinolincyanin. Of these new dyestuff's are especially distinguished para-toluquinaldin-quinolinalkyleyanin, para - toluquinaldin-para-toluquinolinalkyleyanin, para-toluquinaldin-para-methoxy-quinolinalkyleyanin, para-me. thoxyquinaldin-para-methoxyquinolineyanin, and para-ethoxyquinaldin-para-ethoxyquinolincyanin by their rendering the photographic plate about twice to four times as sensitive to red as the hitherto known quinaldinquinolineyanin.