Ex Parte Ooms et alDownload PDFPatent Trial and Appeal BoardMar 29, 201713280423 (P.T.A.B. Mar. 29, 2017) Copy Citation United States Patent and Trademark Office UNITED STATES DEPARTMENT OF COMMERCE United States Patent and Trademark Office Address: COMMISSIONER FOR PATENTS P.O.Box 1450 Alexandria, Virginia 22313-1450 www.uspto.gov APPLICATION NO. FILING DATE FIRST NAMED INVENTOR ATTORNEY DOCKET NO. CONFIRMATION NO. 13/280,423 10/25/2011 Pieter Ooms 074023-0302-US (286822) 2123 123223 7590 03/31/2017 Drinker Biddle & Reath LLP (WM) 222 Delaware Avenue, Ste. 1410 Wilmington, DE 19801-1621 EXAMINER OTTON, ALICIA L ART UNIT PAPER NUMBER 1626 NOTIFICATION DATE DELIVERY MODE 03/31/2017 ELECTRONIC Please find below and/or attached an Office communication concerning this application or proceeding. The time period for reply, if any, is set in the attached communication. Notice of the Office communication was sent electronically on above-indicated "Notification Date" to the following e-mail address(es): IPDocketWM @ dbr.com penelope. mongelluzzo @ dbr. com DB RIPDocket @ dbr. com PTOL-90A (Rev. 04/07) UNITED STATES PATENT AND TRADEMARK OFFICE BEFORE THE PATENT TRIAL AND APPEAL BOARD Ex parte PIETER OOMS, FRIEDHELM RISSE, ANDRE DUX, 4CARSTEN BUCHALY, THOMAS PANCUR, ARTHUR SUSANTO, GEORG RONGE, JOHAN VANDER EYNDE, and WIM WUYTACK Appeal 2015-003354 Application 13/280,423 Technology Center 1600 Before DONALD E. ADAMS, DEMETRA J. MILLS, and JOHN E. SCHNEIDER, Administrative Patent Judges. MILLS, Administrative Patent Judge. DECISION ON APPEAL This is an appeal under 35U.S.C. § 134. The Examiner has rejected the claims for obviousness. We have jurisdiction under 35 U.S.C. § 6(b). We Affirm. Appeal 2015-003354 Application 13/280,423 STATEMENT OF CASE The following claim is representative. 1. A process comprising purifying dialkyl carbonates of the formula (II) in one or more columns in the presence of an alkylene oxide of the formula (V) and of an alkyl alcohol of the formula (IV) R-—o—C—O—R II O (II) wherein R1 and R2 represent, independently of one another, linear or branched, substituted or unsubstituted Ci-C6-alkyl, R3 and R4 represent, independently of one another, hydrogen, substituted or unsubstituted Ci-C4-alkyl, substituted or unsubstituted C2-C4- alkenyl or substituted or unsubstituted Ce- Ci2-aryl, and R5 represents a straight-chain or branched Ci-C4-alkyl; and wherein the mean residence time of the dialkyl carbonate in the column(s) is from 0.3 h to 3 h. Grounds of Rejection Claims 1-14 are rejected under 35 U.S.C. § 103(a) as being unpatentable over Fukuoka. Claims 1-14 are provisionally rejected on the ground of nonstatutory obviousness-type double patenting as being unpatentable over claims 1-13 of copending Application No. 13/280,438. 2 Appeal 2015-003354 Application 13/280,423 Cited References Fukuoka US 2009/0105495 A1 Apr. 23,2009 copending Application No. 13/280,438 FINDINGS OF FACT The Examiner’s findings of fact are set forth in the Final Action at pages 5-13. The following facts are highlighted. 1. According to Fukuoka |98, The reaction time for the transesterification reaction carried out in step (I) is considered to equate to the average residence time of the reaction liquid in the continuous multistage distillation column A. The reaction time varies depending on the form of the internals in the distillation column A and the number of stages, the amounts of the starting materials fed in, the type and amount of the catalyst, the reaction conditions, and so on. The reaction time is generally in a range of from 0.1 to 20 hours, preferably from 0.5 to 15 hours, more preferably from 1 to 10 hours. 2. According to Fukuoka |72, A cyclic carbonate preferably used in the present invention is one not containing a halogen that has been produced through reaction between, for example, an alkylene oxide such as ethylene oxide, propylene oxide or styrene oxide and carbon dioxide. A cyclic carbonate containing small amounts of such raw material compounds, the dial, and so on may thus be used as a starting material in the present invention. 3 Appeal 2015-003354 Application 13/280,423 PRINCIPLES OF LAW In making our determination, we apply the preponderance of the evidence standard. See, e.g., Ethicon, Inc. v. Quigg, 849 F.2d 1422, 1427 (Fed. Cir. 1988) (explaining the general evidentiary standard for proceedings before the Office). “The combination of familiar elements according to known methods is likely to be obvious when it does no more than yield predictable results.” KSRInt’l Co. v. Teleflex Inc., 550 U.S. 398, 416 (2007). The burden of demonstrating unexpected results rests on the party asserting them, and “it is not enough to show that results are obtained which differ from those obtained in the prior art; that difference must be shown to be an unexpected difference.” In re Klosak, 455 F.2d 1077, 1080 (CCPA 1972). “Unexpected results must be established by factual evidence. Mere argument or conclusory statements in the specification does not suffice.” In re DeBlauwe, 736 F.2d 699, 705 (Fed. Cir. 1984). “[W]hen unexpected results are used as evidence of nonobviousness, the results must be shown to be unexpected compared with the closest prior art.” In re Baxter-Travenol Labs., 952 F.2d 388, 392 (Fed. Cir. 1991). It has been long held that “even though applicant’s modification results in great improvement and utility over the prior art, it may still not be patentable if the modification was within the capabilities of one skilled in the art, unless the claimed ranges ‘produce a new and unexpected result which is different in kind and not merely in degree from the results of the prior art.” In re Huang, 100 F.3d 135, 139, 40 USPQ2d 1685, 1688 (Fed. Cir. 1996) (quoting In re Aller, 220 F.2d 454, 456 (1955), and citing In re Woodruff, 919 F.2d 1575, 1578 (Fed. Cir. 1990)). 4 Appeal 2015-003354 Application 13/280,423 “The evidence presented to rebut a prima facie case of obviousness must be commensurate in scope with the claims to which it pertains.” In re Dill, 604 F.2d 1356, 1361 (CCPA 1979). “It is well established that the objective evidence of nonobviousness must be commensurate in scope with the claims.” In re Lindner, 457 F.2d 506, 508 (CCPA 1972). When a claim defines a composition in terms of ranges of elements, any single prior art reference that falls within each of the ranges anticipates. Atlas Powder Co. v. IRECO Inc., 190 F.3d 1342, 1345. (Fed. Cir. 1999). Rejection 1 The Examiner contends that The [Fukuoka] ‘494 publication teaches a process for producing and subsequently purifying dialkyl carbonates on a large industrial scale by using a multi-stage distillation column (see Abstract). The reference teaches the claimed dialkyl carbonates as Formula (C) at paragraph [0031], as well as the claimed alkyl alcohol (Formula (B) in the prior art), with methanol and ethanol both disclosed at paragraph [0033]. With respect to the presence of the alkylene oxide of Formula (V), the reference discloses at paragraph [0072] that the cyclic carbonate is prepared from an alkylene oxide which is preferably ethylene oxide or propylene oxide (as recited by instant claims 5 and 6). Ans. 5. The Examiner further finds that The prior art as a whole, as evidenced by the general disclosure of the ‘494 publication indicates that the mean residence time of the reaction mixture (including the dialkyl carbonate to be purified) is a result- effective variable that can be routinely optimized by varying the aperture range of the sieve trays in the distillation column within the range indicated as preferable by the ‘494 publication (see paragraph [0095]). Further, regarding overlap in pressure or temperature ranges, it is noted that “[W]here the general conditions of a claim are 5 Appeal 2015-003354 Application 13/280,423 disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation.” See In re Aller, 220 F.2d 454 ... (CCPA 1955). The prior art recognizes the consequences of having too much or too little residence time (increase in side reactions vs. decrease in efficiency). Ans. 6. Appellants contend that Fukuoka does not provide any reason or rationale for a person of ordinary skill in the art to utilize a residence time as claimed. In fact, Fukuoka makes no mention of particular residence times at all. Nor does Fukuoka suggest that residence time is a result effective variable that may be altered or adjusted. Br. 6. Appellants further argue that. “Fukuoda [sic] teaches away from using a short residence time as a person of ordinary skill in the art would not be motivated by the teachings of Fukuoka to use a short residence time but would rather use a long residence time.” Br. 7. Appellants argue that “the Examiner has not demonstrated that carrying out the purification in the presence of an alkylene oxide of the formula (V) as instantly claimed would have been obvious based on the disclosure of Fukuoka. Id. Finally, Appellants argue the unexpectedly superior quality of the obtained dialkyl carbonate where the mean residence time is less than 2 hours is demonstrated by Example 1 in comparison to Comparative Example 1 and 2. Page 16, line 15 though page 17, line 19 and page 17, line 25 through page 19, line 23 of the present specification. ANALYSIS We agree with the Examiner’s fact finding, statement of the rejection and responses to Appellants’ arguments as set forth in the Answer. We find that the Examiner has provided evidence to support a prima facie case of 6 Appeal 2015-003354 Application 13/280,423 obviousness. We provide the following additional comment to the Examiner’s argument set forth in the Final Rejection and Answer. We are not persuaded by Appellants’ arguments. With respect to Appellants’ argument that Fukuoka does not disclose alkylene oxide as in the process, Fukouka discloses that an alkylene oxide such as ethylene oxide may be present in the reaction. FF2. We are also not persuaded by Appellants’ argument that Fukuoka fails to teach the claimed residence time. Fukuoka discloses that the reaction time (equivalent to residence time) for preparation of a diakyl carbonate is “generally in a range of from 0.1 to 20 hours, preferably from 0.5 to 15 hours, more preferably from 1 to 10 hours.” FF1. Appellants’ residence time of 0.3h to 3h falls squarely within Fukuoka’s disclosed preferred residence time range of 1 to 10 hours. “Selecting a narrow range from within a somewhat broader range disclosed in a prior art reference is no less obvious than identifying a range that simply overlaps a disclosed range. In fact, when ... the claimed ranges are completely encompassed by the prior art, the conclusion is even more compelling than in cases of mere overlap. The normal desire of scientists or artisans to improve upon what is already generally known provides the motivation to determine where in a disclosed set of percentage ranges is the optimum combination of percentages.” In re Peterson, 315 F.3d 1325, 1329 (Fed. Cir. 2003). Thus, Fukuka does not teach away from shorter residence times, as residence times as short as 1 hour are disclosed in Fukuoka. Finally we agree with the Examiner that Appellants have failed to provide unexpected results within the scope of the pending claims. Ans. 11- 12. Fukuoka indicates that many variables influence residence time. Residence time “varies depending on the form of the internals in the 7 Appeal 2015-003354 Application 13/280,423 distillation column A and the number of stages, the amounts of the starting materials fed in, the type and amount of the catalyst, the reaction conditions, and so on.” FF1. Furthermore, Appellants’ data in the Specification, Example 1, and Comparative Examples 1 and 2 (Spec. 16-19) are not truly comparative of residence time only. For example, Example 1 is conducted with a bottom evaporator temperature of 102°C, with purification at 10 bar (absolute), and a vapor stream temperature of 137°C. Comparative Example 2 is conducted with a bottom evaporator temperature of 102°C, purification is conducted at 20 bar (absolute), and a vapor stream temperature of 40°C. In other words, Appellants have not held all factors that influence residence time constant, and provided comparative results while changing only the actual residence time. Furthermore, Fukuoka discloses that it was well known in the art from Fukuoka that as, “the residence time increases, and hence side reactions (e.g. a reaction between the reaction product dial and unreacted cyclic carbonate) become liable to occur.” |95. Thus, one of ordinary skill in the art reading Fukuoka would have expected that a shorter residence time would limit the byproducts of side reactions. Expected beneficial results are not evidence of nonobviousness. See, In re Skoner, 517 F.2d 947, 950 (CCPA 1975). Appellants have not provided sufficient evidence of unexpected results, and obviousness rejection 1 is affirmed for the reasons of record. Rejection 2 Claims 1-14 are provisionally rejected on the ground of nonstatutory obviousness-type double patenting as being unpatentable over claims 1-13 of copending Application No. 13/280,438. 8 Appeal 2015-003354 Application 13/280,423 According to Patent Office records, Application No. 13/280,438 is now abandoned, and therefore, this rejection is moot. CONCLUSION OF LAW The cited references support the Examiner’s obviousness rejection, which is affirmed for the reasons of record. All pending, rejected claims fall. The Examiner’s obviousness-type double patenting rejection is now moot. No time period for taking any subsequent action in connection with this appeal may be extended under 37 C.F.R. § 1.136. AFFIRMED 9 Copy with citationCopy as parenthetical citation