Polybutadiene Patent Rivalry Widens Firestone, Montecatini join list of contestants that includes Phillips, Goodrich-Gulf, and Monsanto

opacities was Dr. Anthony C. Greiner at Provincial Mental Hospital in Es-sondale, Vancouver, B.C., where some of the patients using phenothiazines have shown visual impairment. Mél­anine production, he notes, is charac­teristic of schizophrenia. Patients of this type tend to develop deposits of mélanine (opacities) in the eye with or without the use of phenothiazines. However, he says, patients who use phenothiazines tend to develop larger opacities than those who do not re­ceive the drugs.

Studies of ways to reverse and de­crease the amount of mélanine depos­ited in the eye and other parts of the body have also been conducted, Dr. Greiner says. The use of ci-penicil-lanine (a copper chelating agent) coupled with a low-copper diet for more than a year has been effective with patients who had developed the opacities during treatment with phe-nothiazine and had subsequently been released.

Oxazepam. Wyeth's oxazepam (7-chloro -1,3 -hydroxy - 5-phenyl-2H-l,4-benzodiazepin-2-one) is up for FDA approval as a new drug. Oxazepam (Serax) is the first member of a new series of intermediate tranquilizers re­lated to chlordiazepoxide (Librium) and diazepam (Valium).

The 3-hydroxy group on oxazepam is effective in reducing toxicity, Wyeth says. Animal studies at Wyeth have indicated that the ratio of dosage to side effects has been from three to 10 times better for oxazepam than for diazepam or chlordiazepoxide. A comparison of the acute LD50 values in mice shows reduced toxicity: ox­azepam, 5000; diazepam, 720; and chlordiazepoxide, 620 (expressed in mg. per kilogram). The reduced toxicity, Wyeth says, possibly results from the ease of conjugation and sub­sequent elimination of oxazepam as a glucuronide (this metabolic product has been found in dogs).

Clinical response to oxazepam was depicted and summarized in an exhibit by several physicians at the American Academy of General Practice Meeting, in San Francisco, Calif. According to the studies, oxazepam gave good to excellent response in treatment of 85% of patients who had symptoms of psychoneurosis. The investigators found that oxazepam relieves the pa­tient's symptoms without limiting his mental or physical activity, has few side effects, and is relatively free from sedation.

The public record in the polybuta­diene patent situation grows more vo­luminous and more complex. Publica­tion last week of a U.S. Court of Cus­toms and Patent Appeals decision (rendered April 15) added Firestone to the three companies already re­vealed as participants in the struggle-Phillips, Goodrich-Gulf, and Monsanto (C&EN, April 26, page 27). Patent Office records now open to the public reveal that Montecatini also has ap­plied for a polybutadiene patent.

The situation surfaced on April 13 when Phillips received a product pat­ent (U.S. 3,178,402) on cfe-l,4-poly-butadiene. On April 12, Goodrich-Gulf started suit in U.S. District Court in Cleveland asking that the Phillips patent be declared invalid and void.

The contestants are struggling over a product whose current U.S. market amounts to about 115,000 long tons a year. About 90% of it goes into tires. Besides Phillips, Goodrich-Gulf, and Firestone, other U.S. producers in­clude Goodyear and American Rub­ber & Chemical. ( Monsanto does not make polybutadiene.) Total U.S. ca­pacity is 173,500 long tons a year.

In the Firestone decision, the court reversed the Patent Office Board of Appeals on several points. It allowed Firestone to claim in its patent appli­cation invention of a polybutadiene with "at least about 29% of said mon­omer units being present in cis-1,4 structure."

Conflict. The language of this claim appears to be in conflict with that of the Phillips patent. That pat­ent claims invention of, among other things, "a rubbery polymer of 1,3 butadiene characterized by at least 85% cis 1,4 addition."

A principal question before the court in the Firestone case was whether the Firestone claim could be allowed in view of an August 1954 article in Industrial and Engineering Chemistry by Dr. John L. Binder of Firestone. Dr. Binder referred to 100% cw-l,4-polybutadiene in the ar­ticle, stating that it "cannot be made at any practical temperature."

The Patent Office argued that the 1954 Binder article constituted public

disclosure of a high cis-content poly­butadiene. As such, it claimed, the article barred Firestone from claiming invention of a product containing "at least about 29%" cis-1,4 structure be­cause the Firestone claim was not made until about two years later, in August 1956. The patent statute re­quires application to be filed within a year after public disclosure.

Earlier Case. In disposing of this question, the Court of Customs and Patent Appeals relied on a similar case decided in U.S. District Court for the District of Columbia in July 1963. In that case (Phillips Petro­leum Co. vs. David L. Ladd, then Commissioner of Patents), the court held that Phillips' claim to invention of polybutadiene with at least 85% cis-1,4 addition was allowable despite the disclosure in the Binder article. The court stated:

"With respect to products, distin­guishing them from mere names, the involved polymers are defined by crit­ical limitations, were not predictable, differed in kind from the prior art products, had not been made and probably could not have been at­tained, until the present inventors made their discovery . . . .

"Polymers in the instant case differ in kind from the properties of polybu-tadienes of the prior art, and like­wise, have properties which are un­predictable in light of the prior art. Those polymers had not been made by any method of synthesis by skilled workers in the art, including Dr. Binder who made that admission in the reference, although many highly skilled scientists in the art had been working on these projects."

Interferences. That 1963 decision allowed two of the three claims in the patent that has now been awarded to Phillips. About a year after the deci­sion, a process claim in Phillips' appli­cation was declared to be in interfer­ence with the Monsanto and Good­rich-Gulf applications and one product claim (for a product containing "85% cis 1,4 addition") was declared to be in interference with an application of Montecatini. Claims are declared to be in interference when there is a

MAY 3, 1965 C&EN 27

question about which of the appli­cants was first to make the alleged discovery.

The Phillips-Montecatini interfer­ence was resolved in Phillips' favor this past January. Phillips then di­vided its original application and filed a new one containing the claims al­lowed by the court in 1963 and the claim that had been involved in inter­ference with Montecatini's applica­tion. It is this divisional application which became U.S. Patent 3,178,402.

Meanwhile, the interference involv­ing Phillips, Goodrich-Gulf, and Mon­santo was still going on week before last. A hearing was scheduled to take place on April 19 on Phillips' motion to dissolve the interference. The out­come of this hearing has not been made public.

Foote Mineral to Open Lithium Recovery Unit Lithium and other elements can be separated economically from the brine deposits at Foote Mineral's Silver Peak operation in Clayton Valley, Nev., the company told its stockhold­ers at its annual meeting. Solar ponds for evaporating brine have been built near the 25 square miles of salt flat at Silver Peak. Separation of lithium is expected to begin this year. The company expects to set a high rate of commercial production in 1966.

L. G. Bliss, chairman of the board and president of Foote Mineral, says that the probable low costs of the Silver Peak operation offer the possi­bility of new markets for lithium. For example, lower costs might make

lithium's use more attractive as a pseudo catalyst in aluminum potlines to increase pot efficiency. This could double domestic lithium demand. Current domestic demand is between 10 and 13 million pounds a year (as lithium hydroxide monohydrate equiv­alent).

The unique composition of the brine at Silver Peak makes possible the low-cost extraction of lithium, the company says. The brine is 0.04% lithium. By comparison, the Great Salt Lake in Utah is 0.006% lithium. Equally important are the com­parative concentrations of calcium (0.05%) and magnesium (0.06%). In other brines, the high ratio of these elements to lithium (normally about 100 to 1) has discouraged commercial separation of lithium.

First Quarter Earnings Continue to Show Spectacular Gains For more first quarter reports, see CirEN, April 26, page 28

* Earnings!reflect sale of TDI plant in Linden, Ν J . ** Sales figure reflects the sale of two unprofitable divisions.

28 C&EN MAY 3, 1965

NET SALES NET INCOME EARNINGS PER SHARE First First

Quarter 1965 % Change Quarter 1965 % Change First First {millions from First (millions from First Quarter Quarter

Company of dollars) Quarter 1964 of dollars) Quarter 1964 1964 1965 Abbott Laboratories $ 60.8 12 % $ 7.0 11 % $0.48 $0.53 • Allied Chemical 257.4 6 19.4 3 0.71 0.73 Air Products & Chem. 28.3 3 1.6 13 0.70 0.79 Air Reduction Co. 92.6 18 5.9 40 0.83 1.15 American Potash 13.7 20.4 1.7 28.0 0.56 0.72 Atlas Chemical 22.7 8 1.4 65 0.22 0.38 Baxter Laboratories 15.4 18 0.8 27 0.21 0.27 Borden 312.2 4.4 9.6 10.1 0.80 0.86 Cowles Chemical 5.3 10.6 0.2 11.7 0.62 0.69 Dow Chemical 261.6 6.2 21.1 - 0 . 5 0.72 0.70 Foote Mineral Co. 6.3 16.1 0.5 159.8 0.14 0.36 W. R. Grace 223.3 20.9 7.3 - 4.6 0.52 0.48 Koppers 72.2 4 1.9 12 0.72 0.82 Eli Lilly 86.5 23.7 12.7 62.8 0.49 0.79 Michigan Chemical 3.2 14.8 0.2 16.6 0.27 0.32 Mallinckrodt 11.2 11 0.5 42.5 0.77 1.08 Miles Laboratories 34.6 21 2.2 18 0.46 0.55 National Distillers 187.6 0.1 7.3 35 0.40 0.54 National Starch 21.6 8.1 1.2 66 0.32 0.33 Nopco Chemical* 15.8 5 0.7 105.2 0.30 0.61 Parke-Davis 52 10.1 7.6 30.8 0.39 0.51 Chas. Pfizer 132 14.9 14.0 19.2 0.59 0.70 Pittsburgh Coke** 5.7 -39 .7 0.6 25.6 0.35 0.46 Rohm & Haas 81.8 5 8.9 15 1.50 1.73 Schering Corp. 28.6 16 2.6 24 0.52 0.67 Stauffer Chemical 77.7 25 6.7 27 0.55 0.70 Texas Gulf Sulphur 18.7 23 3.3 19 -0 .28 0.33 Union Carbide 483.8 16 51.8 28 1.35 1.72 Virginia Chemicals 4.3 9 0.2 - 2 8 0.33 0.24 Witco Chemical 35.6 9 1.4 8 0.49 0.53