DETAILED ACTION
Claims 1 and 5-10 are currently pending in the instant application.
Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Response to Amendment/Arguments
Applicant's amendments and arguments filed 11/26/2025 have been fully considered but they are not persuasive. Applicant argues the instant application differs from the primary reference of Ackermann in that the starting materials of malononitrile, triethyl orthoformate and acetic anhydride are continuously added into a continuous reaction device while malononitrile, triethyl orthoformate and acetic anhydride are mixed and remaining acetic anhydride is continuously added in prior art of Ackermann. Although Ackermann exemplifies the process as mixing of malononitrile, triethyl orthoformate and acetic anhydride followed by continuous addition of acetic anhydride, Ackermann teaches process can be conducted batchwise or continuously - (see col. 3, lines 52-58). Thus Ackermann teaches that the process may be conducted continuously. Further, it has been established that continuous addition prima facie obvious from batch. See In re Korpi and Gold 193 USPQ 229 (CCPA 1977) and tt is well established that batch and continuous processes are not patentably distinct. See, In re Dilnot, 319 F.2d 188, 138 U.S.P.Q. 248 (C.C.P.A. 1963).
Applicant further argues that the ratio between the materials of malononitrile, triethyl orthoformate and acetic anhydride is 1 : (1.1-1.5) : (2.1-2.5) in the instant application while Ackermann teaches a ratio of 1 : (1.6-6.0) : 0.5 mol. However, Ackermann teaches that the catalyst acetic anhydride can in principle one can use larger amounts (see col. 3, lines 1-2). Further as stated in the Non-Final Rejection, mailed 09/03/2025, other prior art such as Palimkar teaches ratio of malononitrile : triethyl orthoformate : acetic anhydride to 1 : 1.5 : 2.48. MPEP 2144.05 states that a prima facie case of obviousness exists where the claimed ranges or amounts do not overlap with the prior art but are merely close. Additionally, a range can be disclosed in multiple prior art references instead of in a single prior art reference depending on the specific facts of the case. Iron Grip Barbell Co., Inc. v. USA Sports, Inc., 392 F.3d 1317, 1322, 73 USPQ2d 1225, 1228 (Fed. Cir. 2004). Since Ackermann and Palimkar are both directed towards the same process of reacting malononitrile, triethyl orthoformate and acetic anhydride to produce ethoxymethylenemalononitrile, one of ordinary skill in the art would recognize the ratios of the three starting materials can be varied. Further, MPEP 2144.05, Section II also teaches that differences in concentration or temperature will not support the patentability of subject matter encompassed by the prior art unless there is evidence indicating such concentration or temperature is critical. In re Aller, Lacey, and Hall (105 USPQ 233) teaches that the selection of reaction conditions is more optimization by more modification of routine experimentation and within one skilled in the art. Change in temperature, concentration, or both is not patentable modification in the absence of unexpected results which is different in kind and not degree. Given that the prior art of Ackermann teaches yield of product as 98.7% with purity > 99% (see example 1), Applicant’s claimed concentrations do not appear patentable over the prior art.
Finally, Applicant argues that the temperature of the process is 110 to 120 ºC. However, Ackermann teaches the reaction temperature is between 90 ºC to 165 ºC (see col. 3, lines 44-45). According to MPEP 2144.05, Section I, in the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976). As the temperature ranges of the instant claims lay between the ranges disclosed by the prior art of Ackermann, the temperature would be considered obvious.
As a result, the 103 rejections have been maintained.
Maintained Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
Claims 1 and 5-10 are rejected under 35 U.S.C. 103 as being unpatentable over Ackermann (See U.S. Pat. No. 4,468,353, issued 08/28/1984, cited in IDS filed 05/18/2022) in view of Palimkar (see WIPO Pub No. WO 2014/002111, pub. 01/03/2014, cited in IDS filed 05/18/2022).
Ackermann teaches a process for synthesis of ethoxymethylene malonic acid dinitrile comprising mixing of orthoformic acid triethyl ester (i.e. triethyl orthoformate), malonic acid dinitrile (i.e. malononitrile) and acetic acid anhydride (see Example 1, col. 4). Ackermann teaches that during the course of the reaction, acetic acid anhydride is fed in continuously. Further Ackermann teaches that the process can be conducted continuously (see col. 3, lines 52-58). The product is separated through distillation (see Example 1, lines 51-55). Ackermann teaches that the molar ratio of malononitrile to orthoformic acid is 1:1.6-6 (see col. 3, lines 41-44). Throughout the course of the reaction, 12 g of acetic acid anhydride is fed into the reaction. Thus, Ackermann meets the conditions of claim 1 except that the molar ratio of acetic anhydride is taught to be 0.5 mol rather than 2.0-6.0 mol. However, Ackermann teaches that the catalyst acetic anhydride can in principle one can use larger amounts (see col. 3, lines 1-2). Further Ackermann teaches the reaction temperature is between 90 ºC to 165 ºC (see col. 3, lines 44-45) so that the alcohol that forms can be distilled out, and the reaction can be conducted at up to 5 atm, which is 0.50 MPa (see col. 4, lines 3-6), which reads on the limitations of claims 3-4. Ackermann teaches the reaction has ended after 2 to 3 hours, which corresponds to the limitations of claims 7-8. Further, the reaction occurs in the presence of ethanol. Ackermann teaches use of a column reactor for the continuous process (see col. 3, lines 53-58). Ackermann is silent regarding flow rate. However since flow rate is calculated by dividing the volume of fluid passing through a point by the time taken, and the adjustment of particular conventional working conditions (e.g. determining result effective amounts of the ingredients beneficially taught by the cited references), as well as adjustment of reaction temperature, reaction time and use of solvents, rearranging steps in a reaction sequence, is deemed merely a matter of judicious selection and routine optimization which is well within the purview of the skilled artisan (See In re Mostovych, Weber, Mitchell and Aulbach, 339F.2d 455; 144 USPQ 38).
Ackermann does not teach the molar ratio of malononitrile to acetic anhydride to be 1: (2.0-6.0) molar equivalents, it is well known that "in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation”. See In re Swain et al., 33 C.C.P.A. (Patents) 1250, 156 F.2d 239, 70 USPQ413. In re Aller, Lacey, and Hall (105 USPQ 233) teaches that
“Normally, it is to be expected that a change in temperature, or in concentration, or in both, would be an unpatentable modification. Under some circumstances, however, changes such as these may impart patentability to a process if the particular ranges claimed 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 Dreyfus, 22 C.C.P.A. (Patents) 830, 73 F.2d 931, 24 USPQ 52 ; In re Waite et al., 35 C.C.P.A. (Patents) 1117, 168 F.2d 104, 77 USPQ 586 . Such ranges are termed “critical” ranges, and the applicant has the burden of proving such criticality. In re Swenson et al., 30 C.C.P.A. (Patents) 809, 132 F.2d 1020, 56 USPQ 372 ; In re Scherl, 33 C.C.P.A. (Patents) 1193, 156 F.2d 72, 70 USPQ 204.”
When In re Aller is applied to Ackermann, that the molar ratio of malononitrile to acetic anhydride would be unpatentable. See MPEP 2144.05
Palimkar teaches ratio of malononitrile : triethyl orthoformate : acetic anhydride as 0.302 : 0.454 : 0.75 which corresponds to 1 : 1.5 : 2.48 (see Example 3, Step 1, p. 37), which reads on the ranges of claim 1-2.
A person having ordinary skill in the art following the teachings of Ackermann would have found it prima facie obvious to apply the amounts of reactants taught by Palimkar to the conditions of Ackermann, thereby arriving at the limitations of the instant claims.
Conclusion
THIS ACTION IS MADE FINAL. Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
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/KAREN CHENG/Primary Examiner, Art Unit 1623
/ADAM C MILLIGAN/Supervisory Patent Examiner, Art Unit 1623