DETAILED ACTION
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
The amendment filed on 03/12/2026 has been entered. Claims 1-5 and 7-16 are pending in the application. Applicant’s amendments to the claims have not introduced new matter and are supported in the specification in at least the claims filed 03/12/2026.
Response to Arguments
Applicant's arguments filed 03/12/2026 have been fully considered but they are not persuasive.
Applicant argues Wu’s taught examples disclose a preparation procedure that includes adding TEA over 4-5 hours followed by stirring for about 20 hours, while a second preparation includes TEA addition over 15 minutes and stirring for 4 hours. Applicant argues the instant application has achieved the unexpected result that demonstrates additional aging time is not required. Applicant argues the continuous process is readily controlled and achieves an equal level of yield without external heat control.
However, this is not found persuasive because a reference may be relied upon for all that it would have reasonably suggested to one having ordinary skill in the art, including nonpreferred embodiments. Disclosed examples and preferred embodiments do not constitute a teaching away from a broader disclosure or nonpreferred embodiments (see MPEP 2123 [R-5]). Although Wu does not explicitly list specific examples of performing the process from 0.01 seconds to 20 minutes falling within the instantly claimed ranges, the broader teachings of Wu of a reaction duration in the range of about 10 minutes to about 20 hours, depending on the reaction conditions, such as reaction temperature, extent of agitation and the like (col. 2, lines 45-48) overlaps the range required by the claim. As such, Wu presents a prima facie case of obviousness over the instantly claimed total process time.
Examiner notes arguments directed to the heat are not claimed in claim 1. Where such reaction conditions are claimed in claim 3, Wu teaches the reaction is carried out at about 0° C or below under an inert gas atmosphere. An atmosphere (i.e. 1 atm) is equivalent to 1.01325 bar. In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. MPEP 2144.05 (I). In the instant case, the ranges taught by Wu (about 0° C or below ; 1.01325 bar) overlaps with the claimed ranges (from -78°C to 10 °C; pressure 1 bar to 10 bar). Therefore, the ranges in Wu renders obvious the claimed ranges.
Applicant compares preparation examples 1-6 (a continuous process) with preparation example 7 (a batch process) and asserts that the continuous examples achieve comparable yields in significantly reduced times to that of a convention batch process. Applicant argues the unexpected results cannot be dismissed as mere routine optimization.
However, the reaction time is not found to be unexpected because the prior art Wu teaches a reaction time ranging from 10 minutes to about 20 hours. A reference may be relied upon for all that it would have reasonably suggested to one having ordinary skill in the art, including nonpreferred embodiments. Disclosed examples and preferred embodiments do not constitute a teaching away from a broader disclosure or nonpreferred embodiments (see MPEP 2123 [R-5]). Although Wu does not explicitly list specific examples of performing a the process from 0.01 seconds to 20 minutes falling within the instantly claimed ranges, the broader teachings of Wu of a reaction duration in the range of about 10 minutes to about 20 hours, depending on the reaction conditions, such as reaction temperature, extent of agitation and the like (col. 2, lines 45-48) overlaps the range required by the claim. As such, Wu presents a prima facie case of obviousness over the instantly claimed total process time.
Additionally, because Wu teaches an overlapping reaction time for a batchwise process (10 minutes to 20 hours), Applicant arriving at a continuous process that is carried out for 0.01 seconds to 20 minutes does not constitute an effective showing of criticality when all of the presented data for reaction duration (10 minutes; see Example 1-6, Pg. 37, line 16-Pg. 40, lines 20) overlap the range taught by Wu.
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 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 1-5 and 7 are rejected under 35 U.S.C. 103 as being unpatentable over Wu (US5130458A; US5130458A; cited in IDS dated 11/22/2024).
Regarding claim 1, Wu teaches a method of preparing bis(1,5-cyclooctadiene)nickel(0) by reacting a nickel salt with a reducing agent in the presence of 1,5-cyclooctadiene (Abstract; Claims 1, 3, 10). The complex bis(1,5-cyclooctadiene)nickel(0) is a zero-valent nickel compound, as denoted by the “(0)” following nickel and meets the limitation of manufacturing a zero-valent nickel compound.
Wu further teaches a reactor is used that comprises triethylaluminium (TEA) as reducing agent, Ni(II) acetylacetonate dihydrate as nickel source, and 1,5-cyclooctadiene as the diene source (col. 3, Example 1 and 2). Wu teaches the addition rate of the TEA reagent is controlled so that the temperature does not exceed 0°C and that the addition of 129 g of TEA is carried out over 4-5 hours (col. 2, lines 5-24; col. 3, lines 1-14). Conversion to units of g/min provides an addition rate taught by Wu of the TEA reagent from 0.5375 to 0.42 3 g/min. In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. MPEP 2144.05 (I). In the instant case, the range taught by Wu (0.5375 to 0.42 3 g/min) overlaps with the claimed range (reducing agent supply rate from 0.5 g/min to 500 g/min). Therefore, the range in Wu renders obvious the claimed range.
Wu does not explicitly state the reactor is “continuous.”
However, Wu teaches a batchwise process of preparing a zero-valent nickel complex comprising a reducing agent and a diene. Courts have held a claimed continuous operation would have been obvious in light of the batch process of the prior art. Accordingly, performing the batchwise process of Wu would be obvious to a skilled artisan in the absence of unexpected results. See MPEP 2144.V.E.
Wu does not explicitly disclose “supply rates of the nickel(II) source, the diene-based compound and the reducing agent are the same as or different from each other, and are each from 0.5 g/min to 500 g/min.” Rather, as stated above, Wu teaches only the supply rate of the reducing agent, TEA.
However, Wu further teaches “any suitable concentrations of the solutions can be employed, preferably about 1-10 mole/l of 1,5-cyclooctadiene and about 0.5-3 mole/l of the alkylaluminium compound(s). Any suitable molar ratios of the process ingredients can be employed. It is a critical feature of this invention to employ a molar ratio of the at least one alkylaluminium compound to Ni(II) acetylacetonate hydrate of at least about 1.5:1, preferably about 1.5:1 to about 5:1, more preferably about 1.8:1 to about 2.5:1. The molar ratio of 1,5-cyclooctadiene to the Ni(II) acetylacetonate hydrate generally is in the range of about 1:1 to about 20:1, preferably about 4:1 to about 8:1.” (col. 2, lines 26-38). Wu teaches the addition rate of the TEA reagent is controlled so that the temperature does not exceed 0°C and that the reaction goes to competition with high yields (89-92%, Examples I and II, col. 3, line 1-col. 4, line 13).
In the absence of unexpected results, the specific nickel source and diene supply rate is not considered to confer patentability to the claims. From the disclosure of Wu, a skilled artisan would be motivated to control the reducing agent addition rate to the reactor in order to obtain the benefits of controlling the reaction temperature and obtaining the product in high yields, as taught by Wu. Further, in the absence of unexpected results, a skilled artisan would not expect the flow rates of the nickel source or diene to negatively affect the result of the reaction, as Wu teaches a high yield of zero-valent nickel diene complexes can be obtained without explicitly adjusting these parameters. As the nickel source and diene supply rate is a variable that can be modified, among others, by adjusting the amount of nickel source and diene in the synthesis, the precise amount would have been considered a result effective variable by one having ordinary skill in the art at the time the invention was made. As such, without showing unexpected results, the claimed amounts cannot be considered critical. Accordingly, one of ordinary skill in the art at the time the invention was made would have optimized, by routine experimentation, the amount of nickel source and diene in the synthesis to obtain a zero-valent nickel complex (In re Boesch, 617 F.2d. 272, 205 USPQ 215 (CCPA 1980)), since it has been held that where the general conditions of the claim are disclosed in the prior art, discovering the optimum or workable ranges involves only routine skill in the art. (In re Aller, 105 USPQ 223). See MPEP 2144.05.II.
Wu teaches the reaction duration is in the range of about 10 minutes to about 20 hours, depending on the reaction conditions, such as reaction temperature, extent of agitation and the like (col. 2, lines 45-48). In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. MPEP 2144.05 (I). In the instant case, the range taught by Wu (about 10 minutes to about 20 hours) overlaps with the claimed range (from 0.01 seconds to 20 minutes). Therefore, the range in Wu renders obvious the claimed range. Regarding claim 2, Wu teaches the method of claim 1 and Wu further teaches a reactor is used that comprises triethylaluminium (TEA) as reducing agent, Ni(II) acetylacetonate dihydrate as nickel source, and 1,5-cyclooctadiene as the diene source (col. 3, Example 1 and 2). Wu teaches the addition rate of 129 g of TEA is carried out over 4-5 hours, while nickel (II) acetylacetonate dihydrate and 1,5-cyclooctadiene are supplied to the reactor (col. 2, lines 5-24; col. 3, lines 1-68; Claim 1, 8).
While Wu does not explicitly describe “continuous channels” being used in the synthesis, a “channel” is interpreted as an input unit (or injection unit) for adjusting an input amount of each raw material in the continuous reactor from at least Pg. 12, lines 8-15. Accordingly, Wu teaching that the nickel reagent, the diene source, and the reducing agent are all supplied to the reactor in specific amounts, Wu teaches the “channels” required by the claim. Furthermore, as stated above in the claim 1 rejection, Wu teaches a batchwise process of preparing a zero-valent nickel complex comprising a reducing agent and a diene. Courts have held a claimed continuous operation would have been obvious in light of the batch process of the prior art. Accordingly, performing the batchwise process of Wu would be obvious to a skilled artisan in the absence of unexpected results. See MPEP 2144.V.E.
Regarding claim 3, Wu teaches the reaction is carried out at about 0° C or below under an inert gas atmosphere. An atmosphere (i.e. 1 atm) is equivalent to 1.01325 bar. In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. MPEP 2144.05 (I). In the instant case, the ranges taught by Wu (about 0° C or below ; 1.01325 bar) overlaps with the claimed ranges (from -78°C to 10 °C; pressure 1 bar to 10 bar). Therefore, the ranges in Wu renders obvious the claimed ranges.
Regarding claim 4, Wu teaches the nickel source is Ni(II) acetylacetonate (col. 1, lines 6-16; col. 2, line 5).
Regarding claim 5, Wu teaches the diene is 1,5-cyclooctadiene (col. 1, lines 10-16; col. 1, lines 24-32).
Regarding claim 7, Wu teaches the reaction is generally carried out with agitation (preferably stirring) under a dry, inert gas atmosphere (preferably dry N2 or He or Ar) (col. 2, lines 20-25).
Claim 8 is rejected under 35 U.S.C. 103 as being unpatentable over Wu (US5130458A; cited in IDS dated 11/22/2024) in view of Tomov et al. (US6818714; cited in IDS dated 01/31/2023).
Regarding claim 8, Wu teaches the method of claim 1 and the claim further requires “continuously supplying the zero-valent nickel compound to a second continuous reactor continuously connected to the first continuous reactor.”
In regard to the continuous supplying, Wu teaches a batchwise process of preparing a zero-valent nickel complex comprising a reducing agent and a diene (Abstract). Courts have held a claimed continuous operation would have been obvious in light of the batch process of the prior art. Accordingly, performing the batchwise process of Wu would be obvious to a skilled artisan in the absence of unexpected results. See MPEP 2144.V.E.
The claim further requires suppling the zero-valent nickel compound from a first reactor to a second reactor, to which Wu is silent.
Tomov teaches a process for polymerization of olefins with (1,5-cyclooctadienyl) nickel compounds that includes providing a first tube with 1,5-cyclooctadienyl) nickel and transferring the solution to a second reactor (see col. 10, lines 32-53, Example 1; col. 5, lines 26-33).
Advantageously, providing the nickel compound as a separate constituent from a second reactor provides control over the duration of addition of the reagent, allowing temperature control (col. 6, lines 64-col. 7, lines 8).
Thus, prior to the effective filing date of the claimed invention, it would have been obvious to one of ordinary skill in the art to provide the zero-valent nickel compound in a first tube into a second reactor in the method of Wu in order to allow control over the duration of the addition of the reagent and subsequently temperature of the reaction, as taught by Tomov.
Conclusion
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). 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.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Jordan Wayne Taylor whose telephone number is (571)272-9895. The examiner can normally be reached Monday - Friday, 7:30 AM - 5 PM EST; Second Fridays Off.
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/J.W.T./Examiner, Art Unit 1738
/SALLY A MERKLING/SPE, Art Unit 1738
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