final hearing the circuit court decreed that No. 4,321 was valid, and had been infringed, and ordered a reference as to profits and damages and a perpetual injunction against the making, using, or selling of the article designated in No. 4,321 "artificial alizarine," or dyes containing the invention described in and secured by No. 4,321. Afterward there was a final decree against the defendants for $13,326.65 and costs, of which $12,871.86 was for profits made by the defendants, "by the sale of artificial alizarine, in infringement" of No. 4,321. From this decree the defendants have appealed. This reissued patent (No. 4,321) has been adjudicated in the circuit courts in several cases. It was before the circuit court in Massachusetts in February, 1878, and the decision of Judge Shepley is in Badische Anilin and Soda Fabrik v. Hamilton Manufacturing Company (3 Banning & Arden, 235, and 13 O. G., 273) It was also before the circuit court for the southern district of New York, in September, 1878, and the decision of Judge Wheeler is in Badische Anilin and Soda Fabrik v. Higgin (15 Blatchf. C. C. R., 290, and 3 Banning & Arden, 462, and 14 U. G., 414). The decision of Judge Wheeler in the present case, in April, 1879, is in 16 Blatchf. C. C. R., 155, and in 4 Banning & Arden, 215. The patent was also before the circuit court in Massachusetts in September, 1879, and the decision of Judge Lowell is in Badische Anilin and Soda Fabrik v. Cummin: (4 Banning & Arden, 489). In all of these cases the validity of No. 4,321 was sustained.

In the case before Judge Shepley it was held that No. 4,321 was a valid patent for a manufacture and composition of matter, an artificial dye-stuff, called "artificial alizarine," being a new product, produced by a new process, not a chemically-pure alizarine, but having combined with the alizarine in it anthrapurpurine, isopurpurine, and other bodies not known to have existed before they were produced by Graebe and Liebermann, the presence of some of which bodies appeared to much enhance the value of the dye-stuff. It was decided that the defendants had used that article.

In the case against Higgin it was held that the product of the process. described in No. 4,321 contains isopurpurine, anthrapurpurine, monoxanthraquinone, and other ingredients, which were not only not ingredients in pure alizarine or madder alizarine, but did not exist in any dyestuff with chemically-pure alizarine, CH8O4, before that of Graebe and Liebermann, and are useful coloring-agents, so that the product invented is a new composition of matter. It was decided that the defendants had used or sold dye-stuffs substantially the same, though claimed to be the product of a different process.

In the present case it was insisted in the circuit court by the defendants that the patented product was the same thing as the natural dyestuff, alizarine, found in the root of the madder plant, and chemically known by the formula C1HO, and not patentable. But it was decided that the article which Graebe and Liebermann had made synthetically

from anthracine, though having the same chemical fromula as madder alizarine, was essentially different in capabilities and properties from chemically-pure alizarine, madder alizarine, or any coloring matter, before known; that the article dealt in by the defendants was produced by the process of United States Letters Patent No. 154,536, granted July 28, 1874, to Heinrich Caro, Charles Graebe, and Charles Liebermann; that the use of sulphuric acid in the process of the latter patent performs the same office in the same way as the bromine in the process of No. 4,321, and that the products of the two processes are identical.

In the case before Judge Lowell he held that what Graebe and Liebermann sought to discover, and supposed they had discovered, was the alizarine, which is the dye-stuff of madder; that what is called “artificial alizarine" contains inportant dyeing substances not found in madder— namely, anthrapurpurine and isopurpurine (accordingly as these may be two substances or one and the same substance) and flavopurpurinewhich substances produce valuable effects not produced by any extracts from madder; that although the defendant insisted that those new pur purines were not found in the artificial alizarine made by the bromine process of No. 4,321, and were found only in artificial alizarine made by methods invented since Graebe and Liebermann invented that process, and the evidence on that point was in much conflict, yet it was shown that pure alizarine, pure isopurpurine, and pure flavopurpurine were all contained in the patented article; that the artificial alizarine of No. 4,321 is different in some important respects from any article known before; that the new article of manufacture claimed in No. 4,321 was new in fact, and that the infringement was made out.

In Watts' Dictionary of Chemistry, volume 1, page 113, published in 1866, Alizarin is stated to be a red coloring matter obtained from madder, first prepared by Robiquet and Colin. This was in 1826. The correct formula of alizarine, C14H8O4, was first arrived at by Strecker in 1866. It means that there are fourteen atoms of carbon, eight atoms of hydrogen, and four atoms of oxygen in each molecule. At this stage Graebe and Liebermann took up the subject, and treated madder alizarine with the view of determining what was its mother substance. They tell the story themselves in a paper in the record entitled "Artificial Alizarine,” which is a translation from the original, prepared in German by them, contained in the Official Report of the Vienna Exhibition of 1873, and also published separately in 1876. They heated madder alizarine with zine dust, and n:ade the alizarine give up its four atoms of oxygen, and take up two atoms more of hydrogen. They thus obtained a hydrocarbon identical with that found in coal-tar, called "anthracine," and having the formula C14 H10. They then conceived the idea of converting anthracine into alizarine. Anthracine was difficult to obtain, and the experiment was conducted on a small scale. But it resulted in the proc ess described in No. 4,321, of converting anthracine iuto anthrachinon, the formula of which was CH3O2, and then heating the anthrachinon

with bromine and obtaining bibromanthrachinon, and heating that with caustic potash or soda and obtaining alizarine. Graebe and Liebermann thus solved the problem of the synthesis of alizarine. It was a matter of great scientific interest, and gave them much reputation. The paper states that the first method described in No. 4,321for preparing the bibromanthrakinon was so laborious that they devised the other method described of first converting anthraciue into tetrabromanthraciae, and then treating that with nitric acid to obtain bibromanthrakinon. "This method," they state, "made it possible to obtain the alizarine more readily, and aroused hopes of its technical execution," although it involved two more reations than the first method.

In regard to the alizarine thus obtained, the same paper says:

The artificial alizarine, besides having the same composition, had also the same properties as vegetable alizarine. In hydrated alkalies it is soluble, with a blue violet to purple color. The solutions of the alkali salts give with lime, baryta, lead, irou, alumina, and tin salts, lakes corresponding to the madder lakes. Cloth printed with mordants dyes exactly alike with both coloring-matters. From these salt-like compounds yellow flocculent alizarine is set free by the addition of a mineral acid. The artificial coloring-matter shows the same solubilities, and the solutions of the alkaline salts the same absorption spectra, which are known of the natural coloringmatter. The free coloring-matter sublimes in beautiful yellow to red needles, which cluster together like feathers. On oxidizing with nitric acid, phthalic acid and oxalic acid are formed. Heated with ziuc dust, the artificial alizarine is again converted into anthracine.

The paper then proceeds:

The above methods, which now, from a technical point of view, have only a historic interest, and are therefore described without further detail, make up the subject of the patents taken out in England on the 18th of December, 1868, and then also in France, Prussia, most German States, Austria, Russia, and America.

The provisional specification deposited in the English Patent Office, December 18, 1868, which was the date of the patent, gives a short description of the process, and says:

The alizarine prepared in this artificial way is perfectly pure, and can be employed in all the applications for which the different preparations of madder are used. The full specification, filed June 17, 1869, is substantially identical with the specification of No. 95,465, and claims

The artificial production of alizarine by first preparing bibromauthrakinon or bichloranthrachinon, and then converting these substances into alizarine, as herein

described.

In further pursuing the history of the matter the same paper proceeds:

The discoverers of the synthesis of alizarine soon found it necessary to enter into connection with some large dye-factory. This was necessary in order that the raw material could be more easily obtained, and that the experiments could be made on a large scale and further developed. This could be done best with an establishment already in existence, where the doubtful question whether this might be the basis of an industry with hopes of success could be solved. One of the chief difficulties experienced was the fact that the raw material was not only known in commerce, but also in the tar industry, and it was difficult to say whether it could ever be obtained

in sufficient quantity. It was also doubtful whether the artificial alizarine could compete with the natural. Furthermore, there was much difficulty in transferring the above methods to a large scale. Graebe and Liebermann therefore entered into connection with the Baden Anilin and Soda Works in Ludwigshafen, on the Rhine, the largest works of the kind in Germany, even on the continent. [Originally the experiments were limited to the purification of the anthraciue and the manufacture of anthrachinon by the second-mentioned bromine method, because this, notwithstanding its difficluties, showed some hopes of success.]

The passage above in brackets, by another translation reads thus: The first trials principally embraced the purification of anthracine, the manufacture of anthrachinou, and the practical application of the second above-mentioned bromine method as the same, notwithstanding the great difficulties, still gave assurance that it could be used practically.

The paper then goes on:

The latter (meaning the second-mentioned bromine method) was dropped as soon as the observation was made that the alizarine could be made more simply by means of anthrachinon sulpho-acids. Graebe and Liebermann had originally attempted to obtain anthrachinon sulpho-acids by acting on anthrachinon with sulphric acid. But they made the mistake of using too low heats. The temperatures they employed were not high enough, being not greater than those generally employed in the preparation of sulpho-acids. They had also been misled by the observation that anthrachinon could be sublimed unchanged from strongly-heated sulphuric acid. Therefore they hoped little from sulpho-acids, and gave all their attention to improving the above methods. This mistake was avoided, and the modification of the synthesis of alizarine, which forms the basis of the industry of to-day, was discovered first by Heinrich Caro, who, as an officer at the Baden Anilin and Soda Works, made it his task to give, in combination with Graebe and Liebermann, life to the alizarine industry. Caro first noticed that anthrachinon, if heated with sulphuric acid to above 2002, would give sulpho-acids, which, on fusing with hydrate of potash, formed aliarine, the same as the bromine compound. Perkin noticed the same fact shortly after or at about the same time. This method was further developed by Caro aud the original discoverers, and the English patent was taken out on June 25, 1869 (Caro, Graebe, and Liebermann, English patent, 1869, No. 1,936). The patent of Perkin is dated June 26 (Perkin, English patent, 1869, No. 1,948). Two methods were discovered analogous to the two bromine methods. In the first and most important the anthracine is oxidized to anthrachinon. This is converted into sulpho-acids by heating with sulphuric acid to 200° to 260°, and these, by the beautiful method of Kekulé, Wurtz, and Dusart, by fusing with caustic potash or soda, are converted into alizarine. The first process is therefore identical with the first bromine method given above. In the second method, the sulphuric acid acts on the authrachinon in such a manner that, besides the anthrachinon monosulpho-acid as principal product, a small amount of anthrachinon bisulpho-acid is also formed. This was subsequently determined analytically by Graebe and Liebermann. In the patent only the anthrachinon sulpho-acids are mentioned. From analogy, Perkin, in his paper (Jour. Chem. Soc. (2), viii, 133, and Ann. Chem. Pharm., clviii, 335), considered the bisulpho-acid only. It is also found in larger quantity by the excess of acid he employs in his method than it is by the method of Caro, Graebe, and Liebermanu.

The reactions in the second method are then given by formulas, in reference to anthrachinon monosulpho acid and anthrachinon bisulphoacid, and it is then said:

Ou fusing the two sulpho acids they give alizarine exactly like the monobrom and bibron anthrachinou. The anthrachinou bisulpho-acid behaves for the greater part,

if not altogether, like the monosulpho-acid, and furnishes, instead of the corresponding bioxyanthrachinon [which is the alizarine of the process of No. 4,321], essentially trioxyanthrachinon-the isopurpurin.

They then give the two sets of chemical equations, one producing alizarine and the other producing isopurpupin. Further on in the same paper they say:

As far as has been observed, it seems that only the anthrachinon monosulpho-acid will produce alizarine, while the anthrachinon bisulpho-acid produces isopurpurin. In an article by Graebe in the "New Handbook of Chemistry," published in 1871, he had said:

Alizarine, lizaric acid, madder red, matiére colorante rouge, first prepared from madder by Robiquet and Colin (1826), artificially by Graebe and Liebermann (1868), from anthracine. Formula, C14H8O4, is derived from anthracine, and is to be considered as byoxyanthrachinon, C14H8(O2)''(OH)8.

In another publication by Graebe and Liebermann, in 1868, they had said:

By treating alizarine with zinc dust a hydrocarbon was produced having the composition C14H10, and coinciding exactly in its properties with anthracine. According to our experiments alizarine, which is hence a derivative of anthracine, must have the formula C14H8O4.

In another publication by them, in 1869, they had said:

We have produced from anthracine artificial alizarine. The properties of the product obtained by us, as well as the colors which we have produced with the same on mordanted cotton, exhibit perfectly the identity of the artificial alizarine with that obtained from madder-root. The methods which have led to the above results, and which we shall describe later, confirm the accuracy of the rational formula for alizarine recently advanced by us.

Again, in a further publication in 1869, they had said:

In our first notice we have already hinted that we have detected no difference between the natural and artificial alizarine, and that the very characteristic colors which both possess when fixed on cotton mordanted with alumina and iron are perfectly identical. We believe, therefore, that it is with one and the same chemical individual we have to deal, and not with isomerons compounds, of whicl. an extraordinarily great number is conceivable, and of which an example already exists, as we have hinted, in chrysophanic acid. In conclusion, we will call attention to the fact that our production of alizarine is the first example of the artificial formation of a coloring-matter occurring in plants.

The various papers thus referred to are, it is understood, put in evidence by stipulation, with like effect as if the authors of them had testified to the facts stated in them.

In Prussia a patent for five years was granted to Graebe and Liebermann, March 23, 1869, for their bromine process, on condition that it should be put into practical operation in twelve months within the Kingdom. On the 7th of July, 1870, after several notices to them, the patent was declared extinct, because proof had not been produced of the carrying out of the patented methods. In view of what Graebe and Liebermann themselves state in the publication before cited, it is manifest that the Prussian patent was revoked because the process described