Court Opinion

ID: 9450508
Source: CourtListenerOpinion
Date Created: 2023-08-04 16:50:51.427949+00
Date Added: 2024-06-11T17:32:21.807736
License: Public Domain

MARTIN, Judge
(dissenting, with whom ALMOND, Judge, joins).
In the related case, In re Farnham, (PA 7244), 342 F.2d 455, 52 CCPA -, we held that:
“ * * * It seems to us that a person of ordinary skill in this art should be charged with the knowledge of the references as to the availability and use of ion exchange resins in catalyzing chemical reactions and that, as stated by the board:
“ * * * Although the specific reaction claimed is not disclosed by these secondary references, we see no reason to believe it would not be operative when catalyzed with an acidic resin instead of free acid. Obviousness under 35 U.S.C. 103 does not require absolute predictability. In re Moreton, 48 CCPA 875; 1961 C.D. 277; 771 O.G. 295; 288 F.2d 708; 129 USPQ 227.”
The single reason for reversing as to claims 3, 7 and 8 was because those claims called for a pretreatment of the catalyst to reduce its moisture content to below 3% (as disclosed in the specification) . We stated:
“ * * * Appellants appear to have discovered that the desired reaction required pre-treatment of the *463ion-exchange resin catalyst to reduce its moisture content before it could be successfully used in the process. * * *
* * * * * *
“ * * * We think appellants’ recognition of the necessity for low water content in the catalyst is an important and unobvious contribution to this art. * * * ”
I might add that that contribution was the one evident on the basis of the record before us.
The present appeal differs from the former in that one reactant is an aldehyde rather than a ketone. The differences in reactivity are well known in the art as seen in the Jansen reference. Jansen was concerned with the “condensation of a phenol with a carbonyl compound. especially a ketone.” He also found that:
* * * the acid condensation of phenols with formaldehyde, as well as other aldehydes such as acetal-dehyde, propionaldehyde, butyralde-hyde, benzaldehyde and the like is catalyzed by the presence of the above-described catalyst. Such condensations are inherently much more rapid than condensations of phenols with keton.,s and much more likely to lead to resin formation and as such are not generally considered equivalent to condensation of phenols with ketones. However, they are effected even more rapidly by the catalysts of this invention, although, of course, because of their more rapid nature, the advantage in using a catalyst is not so pronounced.”
Jansen’s claims call for carbonyl compounds, which is inclusive of aldehydes and ketones.
The majority opinion in the present case hinges allowance of all the claims on the temperature and mole ratio limitations. That I think is in error. The following table will be helpful in noting the “differences between the subject matter sought to be patented and the prior art.” I think the proper approach is to compare the appealed claims with the examples and disclosure of the references. The similarities ought to be considered in order to show that the differences between the claims and the most similar prior art are such that the subject matter is unobvious, if indeed that is so. Since some terms in the appealed claims are not self-defining, I have added a column headed “Appellants’ Specification” to show the scope intended to be covered by such terms.
It is clear that there are three differences, the catalyst, the mole ratios, and the temperature. That the application of the catalyst to this process would be ob*464vious to one of ordinary skill in this art is evident from our holding in the companion appeal, In re Farnham, supra. I turn then to the remaining limitations.

*463

*464

Temperatures less than 100° C. are shown in Jansen for ketones, and alde-hydes are stated to react more rapidly, therefore temperatures should be at least no higher, thus suggesting temperatures within the terms of the claims. Further, there is some overlap in the temperature with the DeGroote reference for claim 1 which calls for a temperature of “less than about 100° C” [emphasis supplied].
Jansen was relied on to support the . position that use of an excess of phenol would be obvious. He states:
“The proportion of the phenol and ketone reactants, of the acid con*465densing agent and of the catalyst may be varied widely. In general, a molecular excess of phenol, that is, more than two molecular proportions of phenol for each mole of ketone, is advantageous, best results being secured when about 4 to 8 moles of phenol are used for each mole of ketone. The proportion of the acid condensing agent is in no way critical but ordinarily about 0.1 to 0.5 mole of condensing agent is used for each mole of ketone reactant. When anhydrous hydrogen chloride is used as the acid condensing agent, it is most convenient to saturate the reaction mixture therewith.”
We keep in mind the relationship between ketones and aldehydes taught in that reference. Jansen then discloses in his Example X the reaction of 8 moles of phenol with 1 mole of formaldehyde, as acknowledged by appellants’ brief.
The real difference in mole ratios relied on by the majority opinion arises from Jansen’s use of a different catalyst. The majority states:
“ * * * We think this difference in catalysts is highly significant and destroys much of the pertinence of Jansen’s teaching of molar ratios to appellants’ invention.” [Emphasis supplied.]
I think that the teachings of the references referred to above indicate that the present temperature and mole ratio limitations of the claims are no more than those resulting from the routine experimentation which one of ordinary skill in the art would determine in finding the optimum conditions in the operation of the process. There is no real showing of criticality in those limitations.
Concerning the instant catalyst, “a cation exchanging resin,” we know:
“ * * * The catalytic properties of ion-exchange materials have been known for many years, and the newer ion-exchange resins have recently been investigated. The strongly acidic sulfonic acid cation-exchange resins have been shown to be effective as an esterification catalyst for most homogeneous or heterogeneous acid-catalyzed reactions. The strongly basic anion-exchange resins have also been shown to be effective base catalysts. The advantages of the ion-exchange resins as catalysts over the convention soluble acids and bases are: (1) the resulting products are not contaminated by the catalyst, (2) the catalyst can be used over and over again, and (3) the resin catalysts may frequently cause fewer side reactions.” 1
The application of that catalyst to the old reaction of phenol with aldehyde was correctly stated in the companion appeal to be obvious. I do not think the application of cation exchange resins to the instant reaction can “destroy” the pertinence of the teaching of Jansen as to mole ratios. The majority opinion admits as much, stating only that “much of the pertinence” is destroyed.
It is clear that in no single element, including the dried resin, is there criti-cality for the reaction of aldehydes with phenols. The whole concatenation does not impress me as being beyond the skill of the art, as exemplified by the references of record. The companion case In re Farnham, supra, showed a criticality in the dried resin which determined whether or not the process would operate. The claims in that case which defined an operable process, by reciting the pre-dried resin, were held to be patentable over the art of record. No such criticality exists here. The two cases should be consistent.
The majority opinion in this case seems to stand for the proposition that although it is obvious to use a well-known catalyst, the cation exchange resin, to catalyze a well known reaction, the process becomes an unobvious one upon the determination of two operational parameters, temperature and mole ratios, *466although neither is critical to the opera-bility of the reaction with the particular catalyst. I cannot agree and would affirm the rejection of all the claims here as obvious variations of the cited art.

. Eneyc. of Chem. Technology, Vol. 8, Kirk et al. ed. (1952), pp. 16-17.