Application of Hartmut Steppan, August Rebenstock and Wilhelm Neugebauer

394 F.2d 1013, 55 C.C.P.A. 791, 154 U.S.P.Q. (BNA) 143, 1967 CCPA LEXIS 213
CourtCourt of Customs and Patent Appeals
DecidedDecember 28, 1967
DocketPatent Appeal 7831
StatusPublished
Cited by9 cases

This text of 394 F.2d 1013 (Application of Hartmut Steppan, August Rebenstock and Wilhelm Neugebauer) is published on Counsel Stack Legal Research, covering Court of Customs and Patent Appeals primary law. Counsel Stack provides free access to over 12 million legal documents including statutes, case law, regulations, and constitutions.

Bluebook
Application of Hartmut Steppan, August Rebenstock and Wilhelm Neugebauer, 394 F.2d 1013, 55 C.C.P.A. 791, 154 U.S.P.Q. (BNA) 143, 1967 CCPA LEXIS 213 (ccpa 1967).

Opinion

SMITH, Judge.

The principal issues for decision are: (1) whether the compounds defined in appealed claims 17 through 22 would have been obvious to one of ordinary skill in the art within the meaning of 35 U. S.C. § 103; and (2) whether claim 25 is an improper “product-by-process” claim. The Patent Office Board of Appeals 1 affirmed the examiner’s rejection of the claims in issue presented in appellants’ application. 2

The Invention

Appellants’ claimed invention is directed to condensation products of substituted or unsubstituted diphenylamine-4-diazonium salts with formaldehyde. The condensation products, which are polyfunctional diazonium salts, are obtained as phosphates free from metal salts. Appellants’ specification admits that certain polyfunetional diazonium salts are known to the prior art. It states:

It is known to the art to prepare polyfunctional diazonium salts by condensing diphenylamine-4-diazonium salts with carbonyl compounds in the presence of mineral acids. In most instances, condensation of diazonium salts with formaldehyde is effected in sulfuric acid of high concentration; hydrochloric acid has also been used as a condensation medium. Isolation of the products produced by condensation in sulfuric acid is accomplished according to a variety of methods, e. g. by precipitation as zinc chloride double salt, as an acid sulfate, or as a diazo sulfonate. The isolation of the condensation products produced in hydrochloric acid has not been specifically described.

Appellants urge that the known methods of isolation of the diazonium condensation products considerably limit the technical application of these compounds. 3

According to appellants’ method, substituted or unsubstituted diphenylamine-4-diazonium salts of acids having a boiling point below 150° C. are condensed with formaldehyde in a phosphoric acid condensation medium. Either before or after condensation, the anions of the original diphenylamine-4-diazonium salts are removed from the reaction mixture. The polyfunctional diazonium phosphates thus formed are precipitated from the reaction mixture, after dilution of the mixture if necessary, by means of organic solvents, in which the phosphates are either insoluble or soluble with some difficulty. After precipitation, the diazonium phosphates are separated by filtration and dried.

Appellants point out that it is not necessary to effect the actual condensation of the diazonium salts with formaldehyde in phosphoric acid to obtain the polyfunc-tional diphenylamine-4-diazonium phosphates of the invention. Alternatively, *1015 the polyfunctional diazonium salts of acids having a boiling point below 150° C., obtained by condensation of diphen-ylamine-4-diazonium salts with formaldehyde, are dissolved in phosphoric acid and the anions of the dissolved salts are removed from the solution, after dilution if necessary. The formed polyfunctional diazonium phosphates are precipitated by the addition of organic solvents in which the phosphates are either insoluble or soluble with some difficulty and the products are thereafter filtered and dried.

The resultant polyfunctional diazonium salts are acid phosphates which are obtained as solids. Neutral phosphates are obtained by treating solutions of the acids phosphates with an anion exchanger. Upon evaporation of the filtered solution, the neutral phosphates corresponding to the acid polyfunctional diazo-nium phosphates are isolated. Appellants state that the products prepared according to the invention are useful as dyestuff intermediates.

Appellants’ claims

Claim 22 is representative of claims 17 to 22 and is drawn to a class of polyfunc-tional diphenylamine-4-diazonium acid phosphates, where m is 1, or to neutral phosphates where m is 0. The compound is claimed in claim 22 as follows:

22. A compound having the formula

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Bluebook (online)
394 F.2d 1013, 55 C.C.P.A. 791, 154 U.S.P.Q. (BNA) 143, 1967 CCPA LEXIS 213, Counsel Stack Legal Research, https://law.counselstack.com/opinion/application-of-hartmut-steppan-august-rebenstock-and-wilhelm-neugebauer-ccpa-1967.