Prosecution Insights
Last updated: April 19, 2026
Application No. 18/699,166

A PROCESS FOR HYDROTREATMENT OF AROMATIC NITROGEN COMPOUNDS

Non-Final OA §103
Filed
Apr 05, 2024
Examiner
GRAHAM, CHANTEL LORAN
Art Unit
1771
Tech Center
1700 — Chemical & Materials Engineering
Assignee
Topsoe A/S
OA Round
1 (Non-Final)
72%
Grant Probability
Favorable
1-2
OA Rounds
2y 6m
To Grant
83%
With Interview

Examiner Intelligence

Grants 72% — above average
72%
Career Allow Rate
771 granted / 1079 resolved
+6.5% vs TC avg
Moderate +12% lift
Without
With
+11.9%
Interview Lift
resolved cases with interview
Typical timeline
2y 6m
Avg Prosecution
23 currently pending
Career history
1102
Total Applications
across all art units

Statute-Specific Performance

§101
0.9%
-39.1% vs TC avg
§103
66.4%
+26.4% vs TC avg
§102
5.6%
-34.4% vs TC avg
§112
15.8%
-24.2% vs TC avg
Black line = Tech Center average estimate • Based on career data from 1079 resolved cases

Office Action

§103
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 . Summary This is the initial Office action based on application 18699166 filed 4/5/24. Claims 1-15 are pending and have been fully considered. Information Disclosure Statement IDS filed on 4/26/24, and 4/5/24 have been considered by the examiner and copies of the Form PTO/SB/08 are attached to the office action. Drawings The Drawings filed on 4/5/24 are acknowledged and accepted by the examiner. Specification The Specification has not been checked to the extent necessary to determine the presence of all possible minor errors. Applicant's cooperation is requested in correcting any errors of which applicant may become aware in the specification. MPEP § 608.01 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 of this title, 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 1-15 are rejected under 35 U.S.C. 103 as being unpatentable over HOGENDOORN ET AL. (US PG PUB 20110119994) in view of ANDERSSON ET AL. (WO2020083989; 4/30/2020), PAASIKALLIO ET AL. (WO2020239729; 12/3/2020), and MILLER (US PG PUB 20090151233) in their entirety. Hereby referred to as HOGENDOORN, ANDERSSON, PAASIKALLIO and MILLER. Regarding claims 1-15: HOGENDOORN teaches in para [0030] The pyrolysis oil, as referred to in the present invention preferably includes a mixture of oxygenated compounds formed during thermal decomposition of lignin and cellulose, and water generated during the decomposition process and from the initial moisture content of the biomass. In a further embodiment the reference to cellulose may further include hemicellulose. Preferably, the carbon content of the pyrolysis oil lies in the ranges of 45% to 50%. Preferably, the water content is in the range of 0 wt % to 30 wt %, more preferably in the range of 20 wt % to 30 wt %. Further preferably, the pyrolysis oil of the present invention comprises aldehydes in the range of 10 wt % to 20 wt %. Further preferably, the pyrolysis oil comprises carboxylic acids in the range of 10 wt % to 15 wt %. Yet further preferably, the pyrolysis oil comprises carbohydrates in the range of 5 wt % to 30 wt %, more preferably in the range of 5 wt % to 10 wt %. Again further preferably, the pyrolysis oil comprises phenols in the range of 2 wt % to 5 wt %. Again more preferably, the pyrolysis oil comprises furfurals in the range of 1 wt % to 4 wt %, and/or alcohols and ketones. The pyrolysis oil may also contain nitrogen in the range of 0.1 wt % to 0.5 wt %, and sulfur in the range of 0.01 wt % to 0.02% wt %. The presence of water and nitrogen and sulfur containing compounds may make pyrolysis oil not suitable for processing in standard refinery units. HOGENDOORN teaches in para [0033] In step (a), preferably the feedstock, comprising pyrolysis oil, optionally pre-hydrogenated, and hydrogen are contacted with a hydrogenation catalyst under hydro-deoxygenation conditions. Preferably, feedstock and hydrogen are co-currently contacted with the catalyst. HOGENDOORN teaches in para [0034] Hydrodeoxygenation conditions for pyrolysis oil containing feedstocks are known in the art. Preferably, the hydrodeoxygenation temperature in step (a) is in the range of from 200 to 400 C., preferably from 250 to 380 C., more preferably of from 280 to 340 C., yet more preferably of from 290 to 320 C. Reference herein to the hydrodeoxygenation temperature is to the maximum temperature that is occurring in hydrodeoxygenation step (a). Since the hydrodeoxygenation reaction is a strongly exothermic reaction, the temperature in the bottom part of the bed will typically be higher than the temperature in the upper part of the bed. HOGENDOORN teaches in para [0035] The catalyst suitably employed in step (a) may be any catalyst known in the art that is suitable for hydro-deoxygenation reaction under the specific conditions of this reaction such as higher water concentration. The catalyst preferably is a hydrogenation or hydrocracking catalyst comprising metals of Group VIII and/or Group VIB of the Periodic Table of Elements or compounds thereof, as hydrogenating component on a catalyst carrier. The catalyst carrier is preferably inert at the reaction conditions, that is, it is preferably inert as hydrogenating component. Inert herein preferably further refers to a catalyst carrier not dissolving or otherwise decaying under the HDO conditions to avoid e.g. metal leaching or weakening of the catalyst pellets for instance due to the amount of water present in the feed. HOGENDOORN teaches in para [0036] The catalyst preferably comprises a catalyst support and one or more active elements. The active elements may include metals such as Nickel (Ni), Chromium (Cr), Molybdenum (Mo), and Tungsten (W), Cobalt (Co), Platinum (Pt), Palladium (Pd), Rhodium (Rh), Ruthenium (Ru), Iridium (Ir), Osmium (Os), Copper (Cu), iron (Fe), Zinc (Zn), Gallium (Ga), Indium (In) and Vanadium (V) in elementary form, alloys or mixtures of one or more thereof such as, but not limited to Rh--Co--, Ni-- and Ni--Cu, preferably in the form of oxides, sulfides or other metal-organic compounds. Preferably the catalyst in step (a) is a hydroprocessing catalyst comprising Ruthenium, Rhenium, Cobalt, Nickel, Copper, and/or alloys or mixtures of Ruthenium, Rhenium, Cobalt, Nickel, and/or Copper, such as for example Rh--Co-- and/or Ni--Cu, on a catalyst carrier that is inert at the reaction conditions. The catalyst support (or carrier) preferably comprises solid substances with high porosity and able to withstand the temperature, pressure and the environment encountered in a hydrotreatment unit and under the specific HDO conditions, i.e. the presence of relatively large amounts of water in the feed, and preferably is shaped in the form of balls, rings or otherwise shaped extrudates, which may serve as a support for the active elements in the catalyst. The carrier preferably may comprise a refractory oxide or mixtures thereof, preferably alumina, amorphous silica-alumina, titania or silica, ceria, zirconia, or it may comprise an inert component such as carbon or silicon carbide or carbon. Carriers that were found inert under the conditions of step a) are ZrO2, CeO2, CeO2 and/or mixtures thereof such as CeO2--ZrO2, silicon carbide and/or carbon. If a catalyst comprising sulphided CoMo, NiMo or NiW is used, the catalyst may be sulphided in-situ or ex-situ. In the case of in-situ sulphiding, a sulfur source, usually hydrogen sulphide or a hydrogen sulphide precursor, is preferably supplied to the catalyst during operation of the process. The carrier may further comprise a zeolitic compound. Any acidic zeolitic compound having sufficient stability at the reaction conditions to limit catalyst decay may suitably be used. Examples of zeolitic compounds include, but are not limited to, zeolite Y, zeolite beta, ZSM-5, ZSM-12, ZSM-22, ZSM-23, ZSM-48, SAPO-11, SAPO-41, and ferrierite. Examples of suitable catalysts include Rh/SiO2; RhCo/Al2O3; Rh/CoSiO3; RhCo/SiO2; Co/SiO2; Rh/ZrO2; Rh/CeO2; Ni/SiO2; Ni/Cr2O3; Ni/Al2O3; Ni/ZrO2; Ni--Cu/Al2O3; Ni--Cu/ZrO2 and Ni--Cu/CeO2. HOGENDOORN teaches in para [0054] A H2 supply vessel used to feed the autoclave, having a volume of 10.8 L. This vessel was typically loaded with an initial pressure of 400 bar(a). The autoclave was filled with H2 until the desired starting pressure (typically 200 bar(a)) and the valve between the reactor and the supply vessel was closed. Then, the electrical heating jacket and the high intensity hollow shaft stirrer (2000 rpm) were turned on. The typical heating rate was approximately 5.5 C./min until 270 C., being slower after that (.about.4 C./min). More hydrogen was added to the reactor until the desired reaction pressure was reached (typically 290 bar(a)). After the reaction was deemed completed, the H2 supply was stopped and the stirrer was left on for an additional 30 minutes. Then the system was left to cool down overnight. A product containing one aqueous phase (also referred to as aqueous fraction) and one or two phases of partially deoxygenated pyrolysis oil (also referred to as partially deoxygenated pyrolysis oil fractions) was obtained. The partially deoxygenated pyrolysis oil fractions which were a part of the product were filtered (5 .mu.m steel filter) to remove the Ru/C catalyst. The oxygen content of these partially deoxygenated pyrolysis oils obtained after HDO was typically up to 30 wt %. The products obtained are summarized in the Table 1. HOGENDOORN teaches in Example 2 - Partially deoxygenated pyrolysis oil (PDePO), prepared by hydrodeoxygenation of a pyrolysis oil at 340 C. and 290 bar as described in example 1 and having a dry oxygen content of approximately 17 wt % was blended with a hydrotreated Gas Oil (HTGO) in a weight ratio of about 1:4 (1 to 4) and some isopropanol to prepare a feed composition. This feed composition containing about 20 wt % partially deoxygenated pyrolysis oil, about 1.5 wt % isopropanol and about 78.5 wt % hydrotreated gas oil was subjected to the hydrogenation step in a continuous hydrotreatment unit. The catalyst used was a pre-sulphided Nickel-molybdenum hydrotreatment catalyst. The reaction temperature was kept at 300 C. to 320 C. (that is, at 300 C. for 100 hours of runtime and subsequently at to 320 C. for an additional 70 hours of runtime) and the pressure was maintained at 60 bar with 1% H2S in the off-gas. The gas flow rate was 20 Nl/hr. The ratio gas to oil was 2000 Nl/kg and the weight hourly space velocity maintained in the reactor was 1 kg/l/h. The product stream obtained was separated in a gas/liquid separator and analyzed online using gas chromatography (GC) and the liquid phase was analyzed by true boiling point analysis and two-dimensional gas chromatography (2D-GC). The results of the experiment with regard to product yield and product distribution are represented in Tables 2 and 3 ANDERSSON further teaches the process and the apparatus; wherein the process for production of a hydrocarbon fraction suitable for use as jet fuel (80, 224) from an oxygenate feedstock (2, 202), comprising the steps of a. combining the feedstock (2, 202) with a diluent hydrocarbon stream (6, 226) to form a hydrotreatment feed stream (4, 204) to contact a material catalyti- cally active in hydrotreatment (10a, 10b, 10c, 10d, HDO) under hydrotreat- ing conditions to provide a hydrotreated intermediate product (14, 206), b. directing at least an amount of said hydrotreated intermediate product (14, 206) to contact a material catalytically active in hydrocracking (18a, 18b, HDC) under hydrocracking conditions to provide a hydrocracked intermedi- ate product (22, 212), c. separating the hydrocracked intermediate product (22, 212) in a hy- drocracked intermediate liquid fraction (34, 226) and a gaseous fraction (26, 220), d. directing at least an amount of said hydrocracked intermediate liquid fraction (34, 226)) to contact a material catalytically active in hydrodearomatization (90a, 90b, HDA) under hydrodearomatization conditions to provide a treated product (92) comprising the hydrocarbon fraction suitable for use as jet fuel (106, 218). ANDERSSON Figure 1 shows a process layout for production of a hydrocarbon suitable for use as jet fuel (106) from a renewable feedstock (2) added stepwise (2a, 2b and 2c) to a hy- drotreatment section (8). A first amount of the renewable feedstock (2c) is combined with a diluent (6) and directed to a hydrotreatment section (8) where it contacts a mate- rial catalytically active in hydrotreatment (10a). Further amounts of renewable feed- stock (2b, 2c) and an amount of hydrogen rich gas (12a) are directed to contact individ ual beds of catalytically active material (10b, 10c, 10d) under hydrotreating conditions. This provides a hydrotreated intermediate product (14). The hydrotreated intermediate product (14) is directed to a hydrocracking section (16) to contact a material catalyti- cally active in hydrocracking comprising a base metal (18a, 18b) under hydrocracking conditions, as well as a material catalytically active in isomerization comprising a base metal (20) providing a hydrocracked intermediate product (22). In a gas/liquid separator (24) the hydrocracked intermediate product (22) is separated into a gaseous fraction (26) and a liquid fraction (34). The gaseous fraction (26) is split in an optional purge (28) and a recycle gas (30) which is pressurized (32) and directed as quench hydrogen supply of the hydrotreatment section (12a) in one or more positions between reactor beds as well as to the hydrocracking section (12b, 12c). The liquid hydrocracked inter- mediate product (34) is directed to a stripper (36), which also receives a stripping me dium (38) and optionally a stripper overhead recycle (40). From the stripper a gaseous stripper product (42) is directed to a gas/liquid separator (44), from which an off-gas (46) and a light naphtha fraction (48) are withdrawn. An amount of the light naphtha is withdrawn as product (50), an amount (52) may optionally be directed as feed (102) to a kerosene stabilizer (100) and an amount is directed as overhead recycle (40) to the stripper (36). The liquid stripper product (54) is directed to fractionator (56), from which a light overhead stream (58) is directed to an overhead vessel (60), from which a heavy naphtha (62) is withdrawn. An amount of heavy naphtha (64) is withdrawn as product and a further amount (66) is directed as fractionator recycle (66). A bottom fraction (68) is split in to a recycle stream (72) and a reboiled stream (74). From a side column (78) a hydrocracked intermediate jet product (80) is combined with a of hydrogen rich stream (84c) and directed as feed (82) to a hydrodearomatization and hydrodewaxing section (86), where it contacts a material catalytically active in isomerization (88) and a material catalytically active in hydrodearomatization (90a, 90b) under hydrodearomati- zation conditions, receiving further hydrogen rich streams (84a, 84b), providing a treated product (92), which is directed to a product gas/liquid separator (94) from which a second gaseous fraction (96) is withdrawn and combined with the recycle stream (72) and provided as make-up hydrogen in the diluent (76) to the hydrotreatment section (8). An intermediate jet product (98) is withdrawn from the product separator, and di- rected to a further means of separation (100), such as a kerosene stabilizer, optionally also receiving an amount of light naphtha (102), from which a liquid product (104) is withdrawn and split in a hydrocarbon fraction suitable for use as jet fuel (106) and a re- boiler liquid (110). The gaseous overhead from the kerosene stabilizer (108) is com- bined with the gaseous stripper product (42) and directed to a gas/liquid separator (44). In a further embodiment (not shown) the second gaseous fraction (96) is not directed as make-up gas for the hydrotreatment section, but instead directed to the a hydro- dearomatization and hydrodewaxing section (86), possibly requiring an additional com- pressor, but also resulting in added simplicity. In this case make-up hydrogen is then added separately to the hydrotreatment section. In a further embodiment the gaseous overhead from the kerosene stabilizer (92) may be handled in a separate overhead circuit with the benefit of simplicity and independ- ence, but at the cost of extra equipment items for cooling, separation and reflux pumps. In a further embodiment the separator, fractionation and light ends recovery sections can be configured in multiple ways as it is known to the skilled person. If light materials like LPG or propane are valuable, the recovery of these can be improved by using a sponge oil absorption system e.g. using the heavy naphtha from the fractionator over- head as lean oil and returning the rich oil to the stripper. PAASIKALLIO also further teaches the process; wherein A method for preparing fuel components from waste pyrolysis oil (WPO), comprising: a) providing a waste pyrolysis oil, comprising as the major part, such as at least 75 wt%, plastic pyrolysis oil (PPO) and/or tyre pyrolysis oil (TPO), the waste pyrolysis oil comprising as the major part hydrocarbons, and comprising impurities in the form of: - chlorine compounds, comprising at least 20 mg/kg chlorine of the WPO and optionally up to 3500 mg/kg, - nitrogen compounds, comprising at least 50 mg/kg nitrogen of the WPO and optionally up to 10,000 mg/kg, - sulphur compounds, comprising at least 10 mg/kg sulphur of the WPO and optionally up to 15,000 mg/kg; b) purifying the waste pyrolysis oil by subjecting it to a hydrothermal treatment with water or with water having a pH above 7 at 150-450 °C, where the oil to water ratio is from 9:1 to 1:9 (weight/weight), such as from 4:1 to 1:1; c) separating the hydrothermally treated waste pyrolysis oil from the aqueous phase; d) preparing a hydroprocessing feed - consisting essentially of the hydrothermally treated waste pyrolysis oil; or - consisting essentially of a mixture of the hydrothermally treated waste pyrolysis oil and one or more feed(s) selected from the list consisting of oxygen- containing biological oils having less than 50 mg/kg chlorine and less than 1 mg/kg silicon and hydrocarbons having less than 50 mg/kg chlorine and less than 1 mg/kg silicon; e) hydroprocessing the hydroprocessing feed catalytically with hydrogen to cause hydrogenation, and optionally one or more of hydrodeoxygenation (HDO), hydrodesulfurisation (HDS), hydrodenitrification (HDN), hydrodechlorination (HDCI), hydrodearomatization (HDAr), and hydroisomerisation (HI), at a temperature between 200 and 450 °C and at a pressure between IMPa and 25 MPa; f) recovering from the hydroprocessed product at least one hydrocarbon fraction boiling in the liquid fuel range. MILLER further teaches a system comprising: a pyrolysis unit; a hydrotreating unit for hydrotreating at least one of the pyrolyzed component fractions so as to yield one or more hydrotreated fractions; and an isomerization unit for catalytically isomerizing at least one of the hydrotreated fractions so as to yield at least one isomerized product. (see MILLER claim 1and para [0035]). Therefore before the effective filing date of the claimed invention, it would have been obvious to one of ordinary skill in the art to recognize HOGENDOORN, ANDERSSON, PAASIKALLIO and MILLER to operate and function as the claimed invention, and the motivation to combine is that they are from the same endeavor of fuel blend formulations; and one of ordinary skilled in the art would recognize HOGENDOORN, ANDERSSON, PAASIKALLIO and MILLER process and apparatus to be used according to the formulator desire. From the teachings of the references it is apparent that one of ordinary skill in the art would have had a reasonable expectation of success in producing the claimed invention. Therefore, the invention as a whole was prima facie obvious to one of ordinary skill in the art before the effective filing date, as evidenced by the references, especially in the absence of evidence to the contrary. In addition, it would have been obvious to one of ordinary skill in the art to modify the process by varying the claimed ranges; however, no patentable distinction is seen to exist between the reference and the claimed invention absent evidence to the contrary. Especially, 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); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990). Furthermore, the claimed changes in the sequence of performing steps is considered to be prima facie obvious because the time at which a particular step is performed is simply a matter of operator preference, especially since the same result is obtained regardless of when the step occurs. See Ex parte RUBIN, 128 USPQ 440 (Bd. App. 1959). See also In re Burhans, 154 F.2d 690, 69 USPQ 330 (CCPA 1946) (selection of any order of performing process steps is prima facie obvious in the absence of new or unexpected results). With regard to any differences in the claimed conversion amounts, the skilled artisan would have found it obvious to modify the process conditions in order to obtain the desired conversions. Moreover, it is well-established that merely selecting proportions and ranges is not patentable absent a showing of criticality. In re Becket, 33 USPQ 33 (CCPA 1937). In re Russel, 439 F.2d 1228, 169 USPQ 426 (CCPA 1971) Still, a claim containing a “recitation with respect to the manner in which a claimed apparatus is intended to be employed does not differentiate the claimed apparatus from a prior art apparatus” if the prior art apparatus teaches all the structural limitations of the claim. Ex parte Masham, 2 USPQ2d 1647 (Bd. Pat. App. & Inter. 1987) Additionally, “Expressions relating the apparatus to contents thereof during an intended operation are of no significance in determining patentability of the apparatus claim.” Ex parte Thibault, 164 USPQ 666, 667 (Bd. App. 1969). Furthermore, “[i]nclusion of material or article worked upon by a structure being claimed does not impart patentability to the claims.” In re Young, 75 F.2d 996, 25 USPQ 69 (CCPA 1935) (as restated in In re Otto, 312 F.2d 937, 136 USPQ 458, 459 (CCPA 1963)). In In re Young, a claim to a machine for making concrete beams included a limitation to the concrete reinforced members made by the machine as well as the structural elements of the machine itself. The court held that the inclusion of the article formed within the body of the claim did not, without more, make the claim patentable In conclusion, an intended result of a process being claimed does not impart patentability to the claims when the general conditions of a claim are disclosed in the prior art. Furthermore, it has been held that obviousness is not rebutted by merely recognizing additional advantages or latent properties present in the prior art process and composition. Further, the fact that applicant has recognized another advantage which would flow naturally from following the suggestion of the prior art cannot be the basis for patentability when the differences would otherwise be obvious. Ex parte Obiaya, 227 USPQ 58, 60 (Bd.Pat. App. & Inter. 1985). Therefore, it would have been obvious to the person having ordinary skill in the art to have selected appropriate conditions, as guided by the prior art, in order to obtain the desired products. It is not seen where such selections would result in any new or unexpected results. Please see MPEP 2144.05, II: noting obviousness within prior art conditions or through routine experimentation. If it is the applicant's position that this would not be the case, evidence would need to be provided to support the applicant's position. Conclusion Any inquiry concerning this communication or earlier communications from the examiner should be directed to CHANTEL GRAHAM whose telephone number is (571)270-5563. The examiner can normally be reached on M-TH 9:00 am - 7:00 pm. Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice. If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Prem Singh can be reached on 571-272-6381. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300. Information regarding the status of an application may be obtained from the Patent Application Information Retrieval (PAIR) system. Status information for published applications may be obtained from either Private PAIR or Public PAIR. Status information for unpublished applications is available through Private PAIR only. For more information about the PAIR system, see http://pair-direct.uspto.gov. Should you have questions on access to the Private PAIR system, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative or access to the automated information system, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000. /CHANTEL L GRAHAM/ Examiner, Art Unit 1771 /ELLEN M MCAVOY/Primary Examiner, Art Unit 1771
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Prosecution Timeline

Apr 05, 2024
Application Filed
Feb 07, 2026
Non-Final Rejection — §103 (current)

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