Fang v. Hankins

• Decision Date: 18 July 1968
• Docket Number: Patent Appeal No. 7906.
• Citation: 399 F.2d 262
• Parties: James C. FANG, Appellant, v. Elinor M. HANKINS and William D. Emmons, Appellees.
• Court: U.S. Court of Customs and Patent Appeals (CCPA)

399 F.2d 262 (1968)

James C. FANG, Appellant, v. Elinor M. HANKINS and William D. Emmons, Appellees.

Patent Appeal No. 7906.

United States Court of Customs and Patent Appeals.

July 18, 1968.

Raymond E. Blomstedt, A. Newton Huff, James T. Corle, Wilmington, Del., (Frederick Schafer, Washington, D. C., of counsel) for appellant.

John F. Bergin, Carl A. Castellan, John C. Martin, Jr., Philadelphia, Pa., (Fidelman & Wolffe, Washington, D. C., of counsel) Alvin M. Esterlitz, Philadelphia, Pa., for appellees.

Before WORLEY, Chief Judge, RICH, SMITH and ALMOND, Judges, and WILLIAM H. KIRKPATRICK^*.

WORLEY, Chief Judge.

Fang appeals from the decision of the Board of Patent Interferences, which awarded to the senior party, Hankins and Emmons (Hankins), priority of invention of the subject matter of thirteen counts corresponding to claims 1-5, 7, 9, 10, 12, 14, 15, 17 and 19 of the Hankins patent.¹ Because Fang filed his application after the Hankins patent issued, he has the burden of proving priority beyond a reasonable doubt. Conner v. Joris, 241 F.2d 944, 44 CCPA 772, (1957).

The subject matter of the counts relates to certain monomeric acrylic acid and methacrylic acid esters of hydroxyalkyl oxazolidine compounds, polymers and copolymers of those monomers, and processes of preparing the monomers. Fang has presented testimony and documentary exhibits relating to activities beginning in March 1954 which, he contends, establishes reduction to practice of

(1) the specific monomers² of counts 4, 5 and 7 — 3-methacryloxyethyl oxazolidine (hereafter MEO), 3-acryloxyethyl oxazolidine (AEO) and 3-methacryloxyethyl - 2 - spirocyclohexyl oxazolidine (MESO), respectively — all falling within the scope of count 1,

(2) the polymers and copolymers of those monomers set forth in counts 2, 3, 9, 10, 12, 14 and 15, and

(3) the processes of counts 17 and 19.

The board held with respect to some of Fang's evidence that it did not prove beyond a reasonable doubt that the materials and processes of the counts were actually prepared and carried out. In those instances where the board either found or assumed the compositions of the counts had been prepared, it held that Fang had not proved beyond a reasonable doubt that those compounds were useful at any time prior to Hankins' filing date. It is those holdings which frame the issues³ before us.

The story begins on March 30, 1954, when Nehf, Fang's assistant, reacted diethanolamine and cyclohexanone to form HESO, recording the results of that experiment on a page of Fang's notebook in evidence as Exhibit 6. Said the board:

* * * Exhibit 6 indicates that the HESO thus formed was refluxed with methylmethacrylate (and also with small amounts of hydroquinone and sodium) and that the material became "quite viscous" before the reaction was discontinued. With respect to this phase of the experiment Nehf testified:

Some MESO may have been prepared here since the reaction of the HESO with the methylmethacrylate did polymerize, and that would be what we would expect under the conditions that we ran this experiment.

It is noted that Exhibit 6 does not indicate that any product was recovered. Further, the record does not show that any analysis was made of any product that may have been formed. In our opinion the testimony of Nehf that "Some MESO may have been prepared" is insufficient to establish beyond a reasonable doubt, that MESO was actually formed. * * *

We find no error in that conclusion. Fang does not appear to press the matter seriously here.

On April 6-7, 1954, Nehf again reacted diethanolamine and cyclohexanone to form HESO, a known material in the prior art. About thirty six cubic centimeters of water was collected from the reaction mixture, corresponding to the theoretical amount of water expected if the reaction proceeded as planned. The product, identified by the code PRC-U93431 L-2 in Exhibit 7, was sent by Fang to Schwarzkopf Microanalytical Laboratory, an independent commercial laboratory, for a determination of the carbon, hydrogen and nitrogen content of the sample. The results, attested to by Drs. Otto and Francine Schwarzkopf, were consistent with the theoretical percentages of those elements in HESO. We may take the preparation of HESO as proved. Hankins does not argue otherwise.

The record shows nothing was done with that sample of HESO until some nine months later, when Gould, another of Fang's assistants, reacted HESO bearing the Code PRC-U93431 L-2 with methylmethacrylate and small amounts of hydroquinone, sodium and methanol. The record shows that the type of reaction sought to be carried out is known as "ester interchange" or "transesterification," in which the methyl alcohol component of the methylmethacrylate ester is "exchanged" for HESO to form MESO. Gould and Fang testified that MESO was prepared. The product was designated PRCE 19149 in Exhibit 12, a notebook record of the experimental procedure dated January 25, 1955, and samples thereof were submitted to Dr. Merrill for a carbon and hydrogen content determination and to Walter for a bromine number determination, the latter being a measure of the amount of unsaturated carbon linkages present. Both Merrill and Walter testified with respect to the procedural aspects of those analyses which are set forth in Exhibits 17 and 18. It appears the product was also analyzed for its saponification number (an indication of its ester content) and subjected to infrared analysis for a determination of its hydroxyl content, the results of which were recorded by Gould in Exhibit 16 along with the results of the carbon, hydrogen and bromine number analyses.

The board stated:

A controversy has arisen between the parties as to the hydroxyl content of PRCE 19149 as shown in Exhibit 16 and the significance thereof. It is stated in Exhibit 16 that "The hydroxyl content of this sample is in the same range as other samples submitted in this series (p-107, 108) according to I. R. analysis R. M. Z." The pages 107 and 108 appear as Exhibits 14 and 15. Gould testified that R. M. Z. were the initials of the analyst who reported the I. R. analysis. Page 108 of the notebook (Exhibit 15) includes a similar statement as to hydroxyl content and refers to page 107 (Exhibit 14). Exhibit 14 states as an objective "To determine purity of 5-methylol-5 ethyl-2-methyl-2-ethyl-1,3-dioxane" and includes the statement "No starting material (1,1,1-trimethylol propane) can be detected in the sample by I. R. analysis."

It is contended by Fang the I. R. analysis in Exhibit 14 clearly shows that the sample did not contain hydroxyl groups and the necessary conclusion is that the sample analyzed did not contain either the starting hydroxy compound nor the hydroxy-containing compound named at the top of the exhibit. It is to be noted that Exhibit 14 does not include any statement that the material is free from all hydroxy containing compounds. It is stated only that no 1,1,1-trimethylol propane, the starting material, can be detected by the I. R. analysis. In our opinion this statement cannot be construed to mean that no hydroxyl group is present when the objective was to determine the purity of a compound stated to have a methylol (a hydroxyl containing) group. We find no basis for concluding that none of the compound named in Exhibit 14 was present. Since Exhibit 16 indicates that the hydroxyl content of the sample of PRCE-19149 is "in the same range as" the sample of Exhibit 14 (stated to be a hydroxyl containing 1,3-dioxane compound) we agree with Hankins et al. that the logical conclusion would be that the sample of Exhibit 16 contains hydroxyl groups to substantially the same extent as the hydroxy compound of Exhibit 14. Gould testified * * * only that the hydroxyl content, as reported, is in the same range as other samples submitted in this series. It is conceded that MESO itself has no hydroxyl group.

Although both Gould and Chalmers, who signed Exhibits 14, 15 and 16 as a witness, testified (almost 10 years after the experiments and tests were performed) that it was their conclusion that the product tested (Exhibit 16) was MESO, it is our view that the showing in Exhibit 16 as to the hydroxyl content of the product raises a doubt as to whether the product PRCE-19149 was actually MESO. * * *

Here Fang urges the board erroneously assumed the PRCE-19149 product of Exhibits 12 and 16 contained hydroxyl groups without the benefit of any evidence that the products discussed in Exhibits 14-16 actually contained hydroxyl groups. Hankins points to a sentence⁴ in Exhibit 14 indicating that the product reported to have been analyzed therein had an actual hydroxyl percentage of 7.9% uncorrected for acid number as compared to a calculated value of 9.05%. We think the board was warranted in concluding that PRCE-19149 had a hydroxyl content "in the same range", viz. about 7.9%.

Alternatively, even if PRCE 19149 did have a hydroxyl content, says Fang, that fact is not necessarily inconsistent with that product being identified as MESO "because hydroxy compounds are obviously a common and natural impurity of MESO." He points out that the starting material, HESO, was an alcohol as was the solvent and theoretical by-product, methanol. It is his position that the infra-red analysis is not in conflict either with the testimony of Gould, Fang and Chalmers,⁵ all of whom concluded that MESO had been prepared, or with the results of the carbon, hydrogen and bromine analyses, all of which are said to correlate or be consistent with the identification of PRCE-19149 as MESO.

While we have given full weight to the evidence Fang has submitted to prove that PRCE-19149 was properly deemed to be MESO, his burden here, however, is to prove that fact beyond a reasonable doubt. Hankins has called our attention to other matters which we think have relevance in determining whether Fang has satisfied his burden of proof:

(1) Hankins questions whether the alleged HESO (...