Application of Steppan
| Decision Date | 28 December 1967 |
| Docket Number | Patent Appeal No. 7831. |
| Citation | 156 USPQ 143,394 F.2d 1013 |
| Parties | Application of Hartmut STEPPAN, August Rebenstock and Wilhelm Neugebauer. |
| Court | U.S. Court of Customs and Patent Appeals (CCPA) |
Joseph Schimmel, Washington, D. C. (Jack E. Armore, Washington, D. C., of counsel), for the Commissioner of Patents.
Before WORLEY, Chief Judge, and Judges RICH, SMITH, ALMOND, and KIRKPATRICK.*
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 Appeals1 affirmed the examiner's rejection of the claims in issue presented in appellants' application.2
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 polyfunctional 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 polyfunctional diphenylamine-4-diazonium phosphates of the invention. Alternatively, the polyfunctional diazonium salts of acids having a boiling point below 150° C., obtained by condensation of diphenylamine-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 diazonium 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 polyfunctional 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:
Claims 17 through 21 vary from claim 22 only as to the presence or absence of alkoxy substituents on the diphenylamine moiety.
The rejection of the foregoing claims under 35 U.S.C. § 103 is based upon the disclosures in the following references:
May 2,266,229 Dec. 16, 1941
Mellan 3,050,502 Aug. 21, 1962
(Filed January 29, 1959)
I. G. Farben (German) 604,278 Oct. 18, 1934
Saunders, "The Aromatic Diazo Compounds", (1949), page 41
The May patent relates to a process for forming dihydrogen diazonium phosphate and comprises the steps of adding dihydrogen phosphate salt to an aqueous solution of diazotized ortho aminoazo toluene and separating the solid diazoazo salt thus obtained. May points out that solid stable diazo salts may be used in printing. In such use, May states that it is desirable that such salts should have a "good solubility," so that heavy, as well as light shades, may be obtained. May specifically suggests that one of the important advantages of the dihydrogen phosphate salt of diazotized ortho aminoazo toluene is that its solubility exceeds that of the acid sulfate salt of diazotized ortho aminoazo toluene, which is in turn more soluble than the zinc chloride, cadmium chloride, and naphthalene disulfonic acid salts of diazotized ortho aminoazo toluene. May further teaches that a solution of certain soluble phosphates used in conjunction with mineral acids will yield, upon admixture with the diazo solution, a solution having a pH falling within the range in which the diazo compound is stable and from which the desired salt is precipitated.
The Mellan patent relates to the preparation of high molecular weight photosensitive diazo compounds. Mellan teaches that diazonium compounds may react with formaldehyde to form certain high molecular weight products in polymer form. Mellan further describes the preparation of a diazo nitroso compound which is "salted out of solution" as the zinc chloride salt. The salts thus described include a nitroso group bonded to the diphenylamine nitrogen atom and are recovered by precipitation with zinc chloride in the form of zinc chloride double salts.
The German Farben patent discloses the diazotization of 4-amino diphenylamine and its derivatives, including alkoxy substituted compounds, to form corresponding diazonium salts, such as double zinc chloride salts of diarylamine-4-diazonium chloride. Farben further teaches that decomposition can be avoided by performing diazotization in the absence of acids and in the presence of zinc chloride. Farben further teaches that bases of the 4-aminodiaryl amine series are useful for the purpose of dye manufacture.
The particular page of the Saunders article which was specifically referred to by the Board of Appeals discloses that diazo compounds form salts with all strong inorganic acids, as well as a number of organic acids. Saunders points out that the diazo compound must appear as the salt of the acid used in the diazotization reaction, unless some form of internal salt formation occurs. Because two molecules of the acid are required, the choice of acid is generally determined by cost and handling convenience.
Appellants have provided us with but a skeletal record which does not contain the necessary materials from which we can determine the exact proceedings prior to the decision of the board. Thus, according to the board, the examiner had rejected claims 17 to 22 as "unpatentable over" Mellan in view of May, Saunders and I. G. Farben. As stated by the board, the examiner's position was that:
* * * varying the anion of an old diazonium salt is a matter of choice and obvious when diazonium phosphates are known and when the anion has little effect on the behavior of the diazonium cation in solution.
The board affirmed that position, stating:
* * * We recognize that no diazonium phosphates having the structure as recited in the appealed claims is disclosed in the prior art, but are of the opinion that the claimed phosphate salts are obvious variations of the salts of the same diphenylamine-4-diazonium compounds conceded by appellants to be known. It is clearly evident from May that phosphate salts of a diazonium compound, albeit not the same as claimed, are more soluble than other salts which are also useful as dyestuff intermediates, and the particular salts claimed, i. e., the phosphates, would thus be obvious when it is desired to utilize a diazonium salt having this particular property. We note, however, that appellants\' specification does not allege any special property for the claimed salts attributable to the specific anion as claimed. Appellants\' argument is apparently based only on the assertion that the references would not suggest the corresponding phosphate salts. We are, however, of the view that the claimed compounds are obvious and suggested by the art.
Appellants, in their brief, emphasize language in the board's opinion in which the board recognized that no diazonium phosphates having the structure set forth in appealed claims 17-22 are disclosed in the prior art. This argument is directed to an issue under 35 U.S.C. 102 which is not here before us. As pointed out in Graham v. John Deere Co., 383 U.S. 1, 12, 86 S.Ct. 684, 15 L.Ed. 2d 545 (1966), novelty of the claimed compound over the prior art,...
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...characteristics to define the invention even though it also contained a reference to how the product was made. Id.; In re Steppan, 394 F.2d 1013, 156 USPQ 143 (CCPA 1967) (The claim referred to a "condensation product." The court found no product-by-process claim.); In re Luck, 476 F.2d 650......
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Atlantic Thermoplastics Co., Inc. v. Faytex Corp., s. 91-1076
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Ex parte Pilchowski
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