APPLICATION OF ACKERMANN

• Decision Date: 08 July 1971
• Docket Number: Patent Appeal No. 8518.
• Citation: 444 F.2d 1172,170 USPQ 340
• Parties: Application of Franz ACKERMANN et al.
• Court: U.S. Court of Customs and Patent Appeals (CCPA)

170 USPQ 340, 444 F.2d 1172 (1971)

Application of Franz ACKERMANN et al.

Patent Appeal No. 8518.

United States Court of Customs and Patent Appeals.

July 8, 1971.

Harry Goldsmith, Upper Montclair, N. J., attorney of record, for appellants. Joseph G. Kolodny, Summit, N. J., Bryant W. Brennan, Fanwood, N. J., of counsel.

S. Wm. Cochran, Washington, D. C., for the Commissioner of Patents. Jack E. Armore, Washington, D. C., of counsel.

Before RICH, ALMOND, BALDWIN and LANE, Judges, and LANDIS, Judge, United States Customs Court, sitting by designation.

BALDWIN, Judge.

This appeal is from the decision of the Patent Office Board of Appeals, adhered to on reconsideration, sustaining the rejection of the single claim in appellants' application¹ as unpatentable in view of the prior art under 35 U.S.C. § 103 and on the ground of res judicata.

THE INVENTION

The sole claim on appeal is as follows:

1. A crystalline product of manufacture consisting of pure a:ß-di-5-methyl-benzoxazolyl-(2) - ethylene, said product existing in the form of fine yellowish needles, and melting at 183 to 184° C, showing in ethanol solution extinction maxima at the wave lengths of ?=350 mµ, ?=362mµ and ?=380 mµ, said product in dioxane solution exhibiting a bluish fluorescence, said product being an optical brightening agent.

THE REFERENCES

The references indicative of the knowledge possessed by one of ordinary skill in this art were all placed in the record by the examiner. Of those supporting the rejection under 35 U.S.C. § 103, Meyer et al.,² the primary reference, was also cited and extensively discussed in appellants' specification. For our purposes, that reference may be said to disclose broadly the class of compounds containing the following atomic skeleton structure:

In the above structure, X may be either an O, S or NH radical. For simplicity, we will use the designation "di-substituted ethylenes" as representing this class of compounds. The patent teaches that these compounds may be prepared by dehydrogenating the corresponding di-substituted ethane with a suitable dehydrogenating agent, and cites a considerable number of such agents any of which would be suitable. It goes on, however, to specify a preference for "mild oxidizing agents, especially mercuric salts." The stated utility for the disclosed compounds is as follows:

The products, when in a dissolved or finely dispersed condition, exhibit a more or less pronounced fluorescence and also possess a more or less marked affinity for cellulose fibres. By virtue of these properties the products are suitable, for example, for identifying materials, for instance, by printing marks thereon which are visible when viewed by light of short wave length.

Of particular pertinence in the Meyer et al. patent is illustrative example 5 wherein is shown the production of the compound a:ß-di-benzoxazolyl-(2)-ethylene, from which the compound of the instant claim differs only in that the benzene rings are substituted at the `5' position with a methyl group. The example concludes with the comment that "a, ß-di-benzoxazolyl -(2) - ethane methylated in the benzene nucleus may also be de-hydrogenated³ in similar manner." (Emphasis added).

Of the secondary references, those relevant to the rejection are Schneider,⁴ Graenacher et al.,⁵ Meyer et al. (II)⁶ and Fry et al.⁷ Meyer et al. (II) and Graenacher disclose di-substituted ethylenes of analogous structure to the claimed compound and said to possess optical brightening properties wherein the corresponding benzene nuclei each contains a methyl or alkyl group in the 5,5' or 6,6' locations. The other two references show similar "methylated" benzene nuclei but on compounds less similar to that now claimed.

THE REJECTIONS

The Prior Art Rejection

The examiner rejected the claim in view of the disclosure of Meyer et al. (I) taken either alone or in combination with the above-mentioned secondary art. His reasoning was stated in the Answer as follows:

Meyer et al. I teach the parent bis benzoxazolyl ethene compound and further show that this compound can be methylated in the benzene nucleus. The most common methylation in the benzene nucleus in this general class of compounds is either 5,5\' or 6,6\' dimethylation * * *. Homologues and suggested derivatives thereof are prima facie unpatentable where the same properties exist for both.

The Res Judicata Rejection

In their parent application, appellants had presented claims reciting only the compounds themselves, one claim drawn specifically to the compound recited in the claim before us now, the others defining the alkyl group on the benzene rings in more generic fashion. These claims were rejected over the combination of Meyer et al. (I) in view of Meyer et al. (II), previously discussed. The examiner there took the position that the claimed compounds were homologous to those described in Meyer et al. (I) and therefore at least prima facie obvious due to the close structural similarity. He was sustained on appeal to the board, which also stated its belief, citing the closing sentences in example 5 of Meyer et al. (I) (also discussed previously), that that reference "substantially anticipates the claims on appeal." Affidavit evidence submitted by appellants, showing that the compounds prepared according to their process were significantly better as optical brighteners for polyester fibers than compounds disclosed in the references and made by the process described therein, was dismissed by the examiner as being apparently based only on purity differences, which he held to be "irrelevant to patentability as claimed". The board indicated that any evidence would be incapable to "render patentable a compound which is clearly lacking in novelty."

Appellants refiled and, in an obvious attempt to get around the criticisms of both the examiner and the board in the parent case, limited their claimed invention to the pure, crystalline, di-5-methylated compound giving the maximum brightening effect. They also submitted additional affidavits showing a comparison of the claimed product with the non-methylated compounds of Meyer et al. (I) when prepared according to appellants' process. This comparison did demonstrate that, when pure, the compounds of the prior art are effective as optical brighteners for polyester fabric, but indicates as well that it would take approximately ten times as much of the pure prior art compounds to produce a brightening effect comparable to that of the claimed product.

The examiner in this case took the position that the subject matter claimed here is the same as that represented by the claim to this compound in the parent case since the parent case showed its preparation in the pure form now recited. He asserted that the issue of purity had been considered in the earlier case and concluded: "The question of patentability over Meyer et al. (I) is no longer a virgin problem and the prior adjudication stands, right or wrong."

THE BOARD OF APPEALS

The board affirmed the rejection over the prior art in this case, adopting the examiner's reasoning as its own. With regard to the combined affidavit evidence of record, the board first observed that the results therein shown apply only to polyester fabrics treated with the claimed material. It then went on to conclude:

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