sulphite-they yield soluble leuco compounds which dye vegetable fibre shades which on washing with water become fixed, being reconverted into the insoluble coloring-matter. The condensation products are all characterized by their solubility in concentrated sulfuric acid, in which they yield from orange to green solutions sulphuric acid, in which they yield from orange to green solutions

AZO DYE.

Paul Julius and Ernst Fussenegger, of Ludwigshafen-on-theRhine, Germany, assignors to Badische Anilin und Soda Fabrik. Patent No. 789,096, dated May 2, 1905.

This invention relates to the production of an azo coloringmatter which, in the form of its lakes, possesses excellent properties, being very stable against the action of light.

Although the azo coloring-matters prepared from a mono-substituted anilin and beta-naphthol disulpho-acid R in the form of their lakes are, as a rule, worthless, the azo coloring-matter prepared by combining diazotized para-chlor-anilin with beta-naphthol sulpho-acid R possesses, in the form of its lakes, very beautiful shades and great coloring power and is also very stable against the action of light.

The coloring-matter consists of a brown-red powder which is easily soluble in hot water. Its barium salt possesses a deep blue-red color and is almost insoluble in water. Upon reduction with tin and hydrochloric acid it yields para-chlor-anilin and amido-naphthol disulpho-acid.

ALIZARIN DYE.

Robert E. Schmidt and Arnold Fischer, of Elberfeld, Germany, assignors to Farbenfabriken of Elberfeld Co., of New York. Patent No. 790,079, dated May 16, 1905.

This invention relates to the manufacture of a new dyestuff of the anthracene series, which can be obtained by treating with formic aldehyde in acid solution the so-called “alizarin-blue,"

(dioxyanthraquinonequinolin obtainable by the action of glycerin and sulphuric acid on beta-nitroalizarin). The new dyestuff thus obtained is when dried and pulverized a dark powder, soluble in concentrated sulphuric acid with a reddish brown and in causticsoda lye and ammonia with a green color. It combines with alkaline bisulphites yielding compounds which are soluble in water and which produce from gray to black level shades on being printed on cotton along with chrome mordants, such as acetate of chrome or the like.

BLUE-SULPHUR DYE AND PROCESS OF MAKING SAME.

Julius Abel, of Mannheim, and Arthur Lüttringhaus, of Ludwigshafen-on-the-Rhine, Germany, assignors to Badische Anilin und Soda Fabrik. Patent No. 790,167, dated May 16, 1905.

The inventors have discovered that by heating an alkali salt of a para-amido-para-,-hydroxydiarylamin body with sulphur new and valuable coloring-matters containing sulphur are obtained which possess the peculiar characteristic that they are difficultly soluble in sodium-sulphide solution in the cold, while in a hot solution they are more readily soluble; but in both cases the solution obtained is almost colorless or possesses only a faint yellow color and no intermediate formation of a blue solution takes place. Vegetable fibre when immersed in a hot solution has an affinity for the colorless leuco compound, and this becomes fixed on the fibre, which remains nearly colorless so long as it is in the solution, but on being exposed to the air becomes blue to violet-blue. In the cold solution the fibre has essentially less affinity for the leuco compound.

The term "para-amido-para-hydroxydiarylamin body" includes the para-amido-para-hydroxydiarylamin itself

and the homologues and substitution products of these compounds. The coloring-matter claimed specifically is that obtainable by heating the alkali salt of para-phenylamido-para-hydroxydiphenylamin with sulphur, and this produces pure-blue shades on vegetable fibre.

NITROAZO DYE AND PROCESS OF MAKING SAME.

John Hagenbach, of Basel, Switzerland, assignor to Anilin Color and Extract Works, formerly John R. Geigy. Patent No. 790,363, dated May 23, 1905.

The nitration of diazo bodies without decomposition has never been effectuated with success until now on account of their lack of stability but it is now found that the diazo body, which is obtained from the 1-amido-2-naphthol-4-sulphonic acid by diazotizing the latter in the presence of a neutral copper salt, can be nitrated without decomposition in the well-known manner, yielding a good crystallizing durable nitrodiazo compound, which when coupled with beta-naphthol gives a novel and very valuable nitro ortho oxy azo coloring-matter, dyeing wool from acid-bath dark reddish brown, which shade after subsequent treatment in the same bath with bichromate turns soot-black, distinguished for an extremely great fastness to the action of light and the processes of milling and potting. The facility with which the said diazo compound can be nitrated is probably based upon the character of the non-nitrated diazo body, which against all expectation and against all analogies is scarcely decomposable in its isolated and dry state. It can be dried without danger of explosion at a temperature of from 80°

to 100° C., and also in dry state it is not explosive. The effect of the nitro group in the combination of this nitro diazo compound with beta-naphthol is a very surprising one in two directions, first, the nitro group multiplies the tinctorial character of the thus-obtained coloring-matter and deepens the shade; secondly, it increases the ability of combination of the diazo compound in a considerable degree.

AZO DYE AND PROCESS OF MAKING SAME.

John Hagenbach, of Basel, Switzerland, assignor to Aniline Color and Extract Works, formerly John H. Geigy. Patent No. 790,364, dated May 23, 1905.

The invention relates to the manufacture of new azo dyes of the naphthalene series, very soluble in water, by sulphonation of the oxyazo dyes obtained by combination of diazo-naphthalsulphoacids with naphthol. These dyestuffs yield on wool dyed in the usual manner and subsequently treated with chromic compounds blue-black shades of very valuable properties.

The coloring-matter obtained by coupling the 1-diazo-2-naphthol4-sulphonic acid or its anhydrid with beta-naphthol dyes wool when after-treated with chrome in blue-black shades of remarkable fastness; but on account of its insufficient solubility in aceticacid solution its application for dyeing in apparatus causes some difficulties. To bring this coloring-matter into a more soluble form when avoiding too high temperatures, which cause the decomposition of the coloring-matter, the sulphonation can be accomplished very easily by aid of concentrated sulphuric acid, especially when mixed with a certain proportion of anhydrous sulphuric acid. The thus-obtained new coloring-matter is extremely soluble in water, but shows, nevertheless, the same excellent solidity against milling and potting as the original coloring-matter. Besides the advantage of the remarkable solubility the new coloring-matter possesses all the same good qualities of the starting stuff.

YELLOW DYE.

Hugo Witter, of Elberfeld, Germany, assignor to Farbenfabriken of Elberfeld Co., of New York, N. Y. Patent No. 791,524, dated June 6, 1905.

This invention relates to the production of new tetrazo dyestuffs which dye wool yellow shades fast to milling and do not stain the interwoven white cotton or wool.

The new dyestuff's can be obtained by combining with two molecular proportions of phenylmethylpyrazolon one molecular proportion of the tetrazotized derivatives of benzidin- or tolidin-metadisulphonic acid having the following general formula:

in which formula X means hydrogen atoms which can be replaced by the methylic group.

The new coloring-matters are in the shape of their alkaline salts yellowish-red powders soluble in water and in concentrated sulphuric acid with a yellow color and yielding upon reduction with stannous chlorid and hydrochloric acid the diamidodiaryldisulfonic acids of the above-given general formula and amido-methylphuric acids of the above-given general formula and amido-methylfast to milling.

YELLOW DYE.

Hugo Witter, of Elberfeld, Germany, assignor to Farbenfabriken of Elberfeld Co., of New York, N. Y. Patent No. 791,525, dated June 6, 1905.

This invention relates to the production of new tetrazo dyestuffs which dye wool yellow shades fast to milling and do not stain the interwoven white cotton or wool.

The new dyestuffs can be obtained by combining with one molecular proportion of phenylmethylpyrazolon and one molecular proportion of alpha-methylindol (methylketol) the tetrazotized