Darsyn Laboratories v. Lenox Laboratories

• Decision Date: 26 March 1954
• Docket Number: Civ. No. 23-50.
• Citation: 120 F. Supp. 42
• Parties: DARSYN LABORATORIES, Inc. v. LENOX LABORATORIES, Inc. et al.
• Court: U.S. District Court — District of New Jersey

120 F. Supp. 42

DARSYN LABORATORIES, Inc. v. LENOX LABORATORIES, Inc. et al.

Civ. No. 23-50.

United States District Court D. New Jersey.

March 26, 1954.

Evans, Hand & Evans, Paterson, N. J., by H. C. Bierman, New York City, for plaintiff.

Jerome J. Heyman, Plainfield, N. J., for defendants Lenox Labs., Inc., Benjamin Pecherer, and William Gerlach.

Adams, Forward & McLean, New York City, by Roger T. McLean, New York City, for defendants Gamma Chemical Corp., J. Robert Fisher and John Robson.

Max Mehler, Newark, N. J., for defendant Irving Biber.

SMITH, District Judge.

This is a civil action under the patent laws, and the jurisdiction of the Court is founded solely on Section 1338 of Title 28 U.S.C., 28 U.S.C.A. § 1338. The complaint is in one count but states two separate and distinct claims: first, a claim against the defendants Gamma Chemical Corporation, hereinafter identified as "Gamma," John Robson, and J. Robert Fisher, for the infringement of a patent of which the plaintiff is admittedly the owner; and second, a claim against all of the defendants for the misappropriation of certain trade secrets and unfair competition. These claims are predicated upon separate and distinct causes of action and must, therefore, be separately considered.

Relationship of the Parties

The plaintiff, a corporation of New Jersey, was organized in March of 1946, and thereafter was engaged in the manufacture of hydroxyquinoline. The defendant Biber was an officer of this corporation until December 2, 1946, when he resigned after selling his stock to the Metalsalts Corporation. Thereafter the defendant Biber organized the Lenox Laboratories, a corporation of New Jersey, which was engaged in the manufacture of hydroxyquinoline until October 17, 1949, or shortly thereafter, when, pursuant to an agreement, it sold its assets, including machinery, equipment and processes, to the defendants Robson, Fisher and Zempliner, who thereafter assigned and transferred these assets to Gamma, a corporation of New Jersey.

Claim for Infringement

The patent in suit pertains generally to the manufacture of 8-hydroxyquinoline, hereinafter identified as "hydroxyquinoline," and relates particularly to the alkali hydrolysis of quinoline-8-sulfonic acid, or its alkali metal salt, from which the hydroxyquinoline is synthesized and isolated. The claims of the patent in suit, construed in the light of the specifications, relate to an improvement on the earlier process of Alkali Hydrolysis, which was concededly old, and are limited to the successive steps therein defined.

The raw material from which hydroxyquinoline is ultimately synthesized is quinoline, a coal tar derivative, synthesized and isolated by the Skraup process, commonly called Skraup's synthesis. Quinoline is a benzo-pyridine, a heterocyclic base, having two dissimilar rings — the benzene and pyridine nuclei — with two ortho-carbon atoms common to both. The hydrogen atoms occupy dissimilar positions relative to the nitrogen atom, and consequently seven mono-substitution products and twenty one di-substitution products, one of which is hydroxyquinoline, are possible for similar substituents. The quinoline compounds have their substituents in the benzene nucleus.

The quinolines possess known chemical properties common to the aromatic hydrocarbons. These properties are ascribable primarily to the presence of the benzene nucleus. The quinolines, like the aromatic hydrocarbons, yield a sulfonic acid upon sulfonation, to wit, the treatment of the quinoline with oleum (sulphuric acid containing approximately 20% of sulphur trioxide, SO3, in solution) at a temperature within the range of 90°C. to 160°C.; an increase in temperature, but within the range, is known to expedite the reaction. The quinoline-8-sulfonic acid thus produced, like the sulfonic acids of the aromatic hydrocarbons, yields the sodium salt upon alkali hydrolysis, to wit, fusion of the sulfonic acid with caustic soda at fusion temperature. These known chemical properties are utilized not only in the manufacture of hydroxyquinoline but also in the manufacture of many derivatives of the aromatic hydrocarbons.

The sulfonation process is one of known utility in the chemical industry, particularly in the synthesis, isolation and manufacture of the derivatives of the aromatic hydrocarbons. It is employed in the manufacture of quinoline-8-sulfonic acid, the raw material from which the sodium salt of hydroxyquinoline is synthesized. It is also employed in the manufacture of sulfonic acids of benzene and naphthalene, the raw materials from which their compounds are synthesized. See "Unit Processes in Organic Synthesis," pages 209 to 271, inclusive, published in 1935 and 1938, "Sulfonation," by Groggins and Simpson. The sulfonation of the aromatic hydrocarbons and the aromatic amines is a separate and distinct process, and is so regarded in the chemical industry. It is generally employed in the manufacture of the intermediate products from which the many derivatives of the aromatic hydrocarbons are synthesized. Ibid.

The claims of the patent in suit are expressly limited to the alkali hydrolysis of quinoline-8-sulfonic acid and its alkali metal salts; in fact, there is no reference in the patent to the sulfonation process. The patentees apparently regarded sulfonation and hydrolysis as separate and distinct processes. The plaintiff here claims an improved process for the sulfonation of quinoline as a trade secret, and an improved process for the hydrolysis of quinoline-8-sulfonic acid as a patentable invention. We purposely refrain from any discussion of the sulfonation process for reasons which are hereinafter discussed.

Prior Art

It was common knowledge long prior to the present invention that quinoline-8-sulfonic acid, or its alkali metal salt, could be converted into the sodium salt of 8-hydroxyquinoline by alkali hydrolysis, to wit, the fusion of quinoline-8-sulfonic acid with caustic soda or potash. This was disclosed by Fischer in a patent (No. 270,045), issued in 1883, and in two earlier articles to which reference is hereinafter made. It was also common knowledge that the process was of particular utility in the hydrolysis of the sulfonic acids of the aromatic hydrocarbons. See "Unit Processes in Organic Synthesis," pages 537 to 574, inclusive, published in 1935 and 1938, "Hydrolysis," by Lloyd.

The process of the Fischer patent is therein described as follows: "In carrying out my invention one part, by weight, of quinoline-sulfonic acid is carefully heated in an iron-melting-pan on an open fire with from one to two parts, by weight, of caustic soda or two or three parts, by weight, of caustic potash. The heating is continued until a sample of the molten mass on being neutralized with hydrochloric acid no longer gives a separation of unchanged quinolinesulfonic acid. When this point has been reached the molten mass is dissolved in water and completely neutralized by hydrochloric acid. The oxyquinoline is then distilled off by a strong current of steam." (Emphasis by the Court.) It is conceded that the molten mass is maintained at a temperature above 310°C. during the reaction.

The process was discussed in two articles (D-G8), published by Bedall and Fischer on March 3 and June 16, 1881. The process defined in the cited patent is more fully explained in the later article, from which we quote: "Concerning the production of hydroxyquinoline the following is to be additionally observed. The quinolinesulfonic acid in powder is, by gradual addition to a two or three fold volume of caustic soda to which a one-quarter part of its weight of water was added, carefully brought to melting point over an open flame, with frequent stirring. After some time the mass (becomes) greenish yellow, and later the smell of quinoline appears. At this moment the melting must be interrupted, as otherwise (considerably more) decomposition takes place. To isolate the formed hydroxyquinoline, the molten mass is dissolved in hydrochloric acid, and the weak acid solution is at once mixed with sodium carbonate and then a strong steam jet is admitted. The hydroxyquinoline is thereby easily volatilized with the steam and condenses in the receiver into beautiful colorless needles." (Emphasis by the Court.)

It will be observed that in the specific process described in the cited patent the hydroxyquinoline is isolated and recovered by the following method: When the reaction is complete the molten mass, which is still at reaction temperature, is dissolved in water to which there is added only sufficient acid, either hydrochloric or sulphuric, to neutralize the solution; the neutralization of the solution isolates the hydroxyquinoline from the sodium salt, the reaction product, and is recovered by distillation. This conclusion is supported not only by the specifications of the cited patent, but also by the article of March 3, 1881, supra.

The article of June 16, 1881 discloses a modified method which may be employed to isolate and recover the hydroxyquinoline. This method comprises the following successive steps: first, the molten mass, which is still at reaction temperature, is dissolved in water to which there is added sufficient acid, either hydrochloric or sulphuric, to insure complete solution of the sodium salt of the hydroxyquinoline, the reaction product; second, the weak acid solution is neutralized by the addition of sodium carbonate, and the hydroxyquinoline is thus isolated from the sodium salt; and third, the hydroxyquinoline is recovered by distillation.

The successive and concomitant steps of the Fischer process, as described in the articles, may be summarized as follows: (a) The fusion kettle is charged with predetermined quantities of sodium hydroxide and quinoline-8-sulfonic acid, preferably two parts of the former to one of the latter; the quinoline-8-sulfonic acid is introduced gradually as the charge is stirred or agitated. (...