E. I. DuPont de Nemours & Co. v. Ladd (328 F.2d 547, 1964)

BASTIAN, Circuit Judge:

In September 1952, two employees of appellant, E. I. Du Pont de Nemours and Company, filed with the United States Patent Office a patent application entitled “Polymerizable Nitrile and Polymeric Product Obtained Therefrom.” Subsequently, Du Pont, applicants’ assignee, duly prosecuted the application in accordance with the requirements of law and the rules of the Patent Office. On September 27, 1957, the Primary Examiner of the Patent Office entered a Final Rejection of all claims included in the application. Du Pont thereupon appealed the final rejection of claim 1 and, in amended form, claims 3 and 4, to the Board of Appeals of the Patent Office, which, on October 17, 1960, rendered a decision affirming the Primary Examiner’s rejection of claims 1, 3 and 4. The Board subsequently denied Du Pont’s petition for reconsideration.

Appellant then filed its complaint against the Commissioner of Patents and the Secretary of Commerce, appellees here, in the United States District Court for the District of Columbia pursuant to 35 U.S.C. § 145, seeking a decree authorizing the Commissioner of Patents to issue Letters Patent on the rejected claims of the patent application. A trial on the merits was had and, on March 20, 1963, the District Court entered an order dismissing the complaint, finding that appellant was not entitled to a patent containing claims 1 and 3. This appeal followed.

Essentially, two issues are presented: (1) whether the compound represented by claims 1 and 3 is unpatentable under 35 U.S.C. § 102; and (2) whether claim 1 is further unpatentable for failure to meet the standards of particularity and distinctness required by 35 U.S.C. § 112.

I

The claims involved here read as follows:

“1. Tetracyanoethylene.

“3. White crystalline monomeric tetracyanoethylene characterized (1) by melting within the range of 195-200°C. in a sealed tube, (2) by being sublimable in air at 120-150°C., (3) by having an infrared absorption spectrum with a divided band characteristic of conjugated unsaturated nitriles, and (4) by formation with toluene of an orange-colored 1:1 complex having a light absorption maximum at 4060A when dissolved therein.”

Tetracyanoethylene is described as an organic chemical compound having extraordinary properties. As indicated by the application, the substance reacts with certain other chemicals to produce strong permanent dyes for synthetic fibers, and its polymers and co-polymers are highly useful as insecticides, as well as motor coil and transformer wire insulation where high temperatures are encountered. The compound itself has the following structural formula:

The tribunals of the Patent Office rejected both claims 1 and 3 on the ground that they had been anticipated, and hence precluded from patentability, by a prior patent (No. 2,264,354) issued to Alder et al. in 1941 entitled “Addition Products of Dienes and Unsaturated Esters, Ketones, or Nitriles.” Included in that patent was the following formula:

“wherein Ri and R2 stand for a member of the group consisting of CN, acyl and an esterified carboxylic acid group,

R3 stands for a member of the group consisting of hydrogen, CN, acyl and an esterified carboxylic acid group and

R4 stands for a member of the group consisting of alkyl, oxalkyl, aryl, CN, acyl and an esterified carboxylic acid group.”

A second reference in the Alder patent found to be significant by the District Court, and indicated on appeal, is the following sentence:

“Examples for the other reaction components falling within the above definition are the products of the condensation of aldehydes and acetyl acetic acid esters or malonic acid esters, furthermore, ethylenetetracarboxylic acid esters, the eorresponding nitriles, and furthermore, the products of the condensation of aldehydes and 1.3-diketones such as acetylacetone.”

The Patent Office argued, and the District Court agreed, that the disclosures made by the earlier Alder patent “would clearly teach a person of ordinary skill in the art that certain chemical structures would be obtained by making directed substitutions in a general formula specifically disclosed,” and that, consequently, the disclosures of the Alder patent were “sufficient under the law to bar a later applicant from obtaining a claim to said chemical structure.” Accordingly, on the basis of Application of Baranauckas, 228 F.2d 413, 43 CCPA (Patents) 727 (1955), the District Court held that appellant was not entitled to a patent on claim 1. Further, while noting that the “pure compound” of claim 3 was not suggested by the Alder patent, the court reasoned that its unique properties could be ascertained only after having successfully produced the compound of claim 1. Thus, claim 1 having been determined to be implicit in the Alder patent, claim 3 was considered merely “an increase in knowledge of a prior disclosure,” and therefore unpatentable under National Lead Co. v. Marzall, 91 U.S.App.D.C. 63, 198 F.2d 296 (1952).

Claim 1.

In Shell Development Co. v. Watson, 102 U.S.App.D.C. 297, 252 F.2d 861 (1958), this court adopted the District Court holding that, in order to defeat a patent application on the basis of 35 U.S.C. § 102(a), a prior publication must “exhibit the thing claimed in such an intelligible manner as to enable persons skilled in the art to which the invention is related, to comprehend it.” Moreover, in Application of LeGrice, 301 F.2d 929, 939, 49 CCPA (Patents) 1124, 1138 (1962), it was said:

“[T]he proper test of a description in a publication as a bar to a patent as the clause is used in section 102 (b) requires a determination of whether one skilled in the art to which the invention pertains could take the description of the invention in the printed publication and combine it with his own knowledge of the particular art and from this combination be put in possession of the invention on which a patent is sought. Unless this condition prevails, the description in the printed publication is inadequate as a statutory bar to patentability under section 102(b).”

In the case before us, three of the four expert witnesses who testified regarding the anticipation of claims 1 and 3 by the earlier Alder patent [Theodore L. Cairns, Louis F. Fieser and Arthur C. Cope] stated that the general Ri, R2, R3, Ri formula gives rise to an infinite number of possible compounds inasmuch as the acyl, alkyl, aryl, oxalkyl and esterified carboxylic acid groups mentioned in the formula represent classes or groups of substituents, within each of which are an infinite (or at least an indefinite) number of specific elements. Hence, even if one were to pick and hold constant a substituent for Ri, R2 and R3 in the general formula, an infinite number of specific compounds would be suggested each time one of the above-named substituents was substituted for Ri. The unequivocal testimony of these three witnesses was that, as a consequence of the vast scope of the general formula, this disclosure in the Alder patent would not suggest tetracyanoethylene to one skilled in the art of organic chemistry. As graphically stated by Dr. Cope:

“Taking all of the possible combinations and permutations of Ri and R2 and R3 and Ri, and recognizing how many of them may be of infinite scope, that formula is just about as broad as the universe; and, in my opinion, it is so broad that it would lead no chemist to the selection of any specific compound falling within that area. * * * I would say that this is so broad that for a chemist to be led to any specific compound by this formula would be just about the same as being led to a specific Chinese baby being born at this moment.”

The District Court, however, based its decision on the cross-examination testimony of Donald J. Cram, the 'fourth of appellant’s experts to testify regarding the scope of the Alder patent. The court stated:

“It appears in the record that Dr. Cram, an expert testifying on behalf of plaintiff stated that if the directions shown by the reference for making the substitutions in the general formula are made ‘you would encounter tetracyanoethylene as the eighth compound,’ and, accordingly, it would appear that the holding of the Baranaukas [BaranauckasJ case, supra, is clearly pertinent and would tained by making directed substitutions, which is exactly equivalent to teach a person of ordinary skill in the art that a structure would be ob-one in which compounds are actually illustrated.”

The court was therefore of the view that since the formula for tetracyanoethylene could be arrived at by a mechanical application of the named substituents in the Alder formula, the earlier patent was an anticipation under 35 U.S.C. § 102, and the present application was properly rejected.

We are of the opinion that a close reading of the entire deposition of Dr. Cram clearly indicates a contrary conclusion. On direct examination, Dr. Cram was shown the Alder patent and asked whether, as a chemist, he would find in the general formula and language of that patent “any description of tetracyanoethylene that is meaningful to you as a chemist?” His answer was:

“If I had never heard the term ‘tetracyanoethylene’ or seen its formula written down and I read this patent I would not consider that I had heard of tetracyanoethylene.”

He further testified:

“I don’t see anything here that would lead me to the structure of tetracyanoethylene in reading of this.

* * -» * *

“I can’t conceive of predicting the properties of tetracyanoethylene as I know them today from anything-that is written down in this patent.”

Under cross-examination by counsel for the Patent Office, Dr. Cram testified that although the cyano (CN) group was the first one mentioned for Ri and R2, it did not stand out from the other groups also mentioned by Alder for Ri and R2. His testimony continued:

“Q. Isn’t it reasonable to assume that one skilled in the art would select the first one mentioned?

“A. Not necessarily. I think he might well pick the one with which he had had the most experience.”

Dr. Cram was then directed by the cross-examiner to assume first that Ri and Rz of the general formula were both CN groups, and then to make the substitutions for R3 and R4 in the order mentioned in the patent. It was only in answer to this restrictive question, relating more to statistical probabilities than to a chemist’s usage of the Alder formula, that Dr. Cram testified:

“Then I believe that you would encounter tetracyanoethylene as the eighth compound.”

Dr. Cram’s testimony on re-direct examination is explanatory of that statement. When asked how many different' organic chemical compounds would be covered if he started with CN groups substituted for Ri, R2 and R3, and then went through all the possible variations for Ri, he stated:

“You could conceive of arriving at this tetracyano compound after listing an infinite number of — almost an infinite number of other compounds, but you would arrive at the tetracyano compound eighth if you are willing to use family structures of compounds and not particular compounds; and that is a thought that my questioner on cross-examination was referring to classes of organic compounds when I ar- . rived at that number eight or eighth, and not to particular compounds.” [Emphasis added.]

It seems clear, therefore, that Dr. Cram’s testimony, viewed in its entirety, indicates his complete accord with the other three expert witnesses regarding the infinite breadth of the Alder formula and the resultant improbability of a skilled chemist being led by that formula to tetracyanoethylene as a specific compound.

A second reference in the Alder patent, “ethylene-tetra-carboxylie acid esters, the corresponding nitriles,” was also urged as a disclosure sufficient to preclude patentability inasmuch as one of the corresponding nitriles of ethylene-tetra-carboxylic acid esters would be tetracyanoethylene. On this point all the expert testimony was uniform that the entire sentence (set forth supra in full) was ambiguous, and that the words “corresponding nitriles” referred not only to ethylene-tetra-earboxylic acid esters, but to all the prior references in the sentence. ' In the words of Dr. Cope:

“I have read this sentence many times, and I find it completely ambiguous. I do not know what is meant by ‘corresponding nitriles.’ * * * I don’t know what a nitrile is corresponding to in any of these classes. That is not a chemically precise definition, and my conclusion would be that, whatever it means, it is of the same infinite scope essentially as the Ri, R2, R3, R