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 .
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 12/8/2025 has been entered.
Claim Status
Claims 1, 57, and 58 were amended and claims 60 and 61 were newly added in the response filed 12/8/2025. Claims 1-10, 12-14, 23-28, and 57-61 are pending and under examination.
Withdrawn Claim Rejections - 35 USC § 112(a)-New Matter
The Applicant’s amendments are persuasive to obviate the 35 USC 112(a) new matter rejection of record on p. 2-3 of the OA dated 9/12/2025. Therefore, the rejection is withdrawn.
Modified 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.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
See p. 3-15 of the OA dated 9/12/2025 for the rejections of record.
Claim(s) 1-10, 12-14, 23-28, and 57-61 is/are rejected under 35 U.S.C. 103 as being unpatentable over Sprecher (“Acyl Azide Synthesis and Curtius Rearrangements in Microstructured Flow Chemistry Systems” J. Flow Chem. 2012, p. 20, of record in the IDS filed on 9/14/2022, of record) in view of Rumi (“Adaptation of an Exothermic and Acylazide-Involving Synthesis Sequence to Microreactor Technology” Org. Proc. Res. Dev., 2009, p. 747, of record), Balci (“Acyl Azides: Versatile Compounds in the Synthesis of Various Heterocycles” Synthesis, 2018, 50, p. 1373-1401), Britton (“The assembly and use of continuous flow systems for chemical synthesis” Nature Protocols, 12, 2017, p. 2423) and Saito (US2011/0052953, published on 3/3/2011).
Applicant Claims
Applicant claims a continuous flow process for producing an isocyanate, the process comprising:
Mixing an acyl hydrazide with an aqueous solution comprising nitrous acid in flow to form a first solution comprising an acyl azide and water;
Mixing an organic solvent with the first solution in flow to produce a second solution comprising the acyl azide, the organic solvent, and water;
Removing water from the second solution in flow to produce a third solution comprising the acyl azide compound and the organic solvent;
Drying the third solution in flow to remove residual water from the third solution;
Heating the third solution comprising the acyl azide compound in flow to produce the isocyanate; and
Isolating the isocyanate.
Determining the Scope and Content of the Prior Art (MPEP §2141.01)
Regarding independent claims 1 and 57, Sprecher discloses a continuous method comprising acyl azide synthesis and Curtius rearrangements in microstructured flow chemistry systems. See abstract. Sprecher teaches the following overall reaction is carried out in the flow reactor:
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. See scheme 1 on p. 20 and discussion thereof. Compound 2 is an acyl hydrazide of claim 13, wherein L1 is an unsubstituted cycloalkylene, and m and n are 0 such that L2 and L3 are absent. Paragraph [0031] of the specification as filed teaches that “cycloalkyl/cycloalkylene” includes “cycloalkenyl/cycloalkenylene”. Compound 3 of Sprecher is an acyl azide of claim 13, and the intermediate between compounds 3 and 4 in step c) is a diisocyanate of claims 12 and 13, wherein L1, L2, L3, m and n are as defined above. Further regarding claim 14, as the claim does not require m and n to be 1, then it is interpreted to mean that any of the L1, L2, or L3 that are present are limited to the recited options. Thus, the unsubstituted C6 cycloalkenyl group of the compounds of Sprecher also meet the limitations of claim 14.
Sprecher teaches that the above process is carried out in the system of Figure 2:
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. See p. 21 and discussion thereof. Thus, Sprecher teaches mixing aqueous NaNO2 and toluene (an organic extraction solvent of claim 3) to form a first solution, which is then reacted with an aqueous solution of the HCl salt of the acyl hydrazide (2) in a mircroreactor (MR) at a residence time (stage) of about 5.4 min to produce a mixture of acyl hydrazide (3), water, and toluene. The reaction between NaNO2 and HCl will form nitrous acid in situ, as evidenced by [0017] of the specification as filed. In this mixture, the acyl hydrazide (3) is more soluble in the toluene phase, and the organic and aqueous phases are separated from one another in an interim separation funnel for a residence time (stage 2) of about 10 min. The organic phase, from which water has been removed, is continuously drawn off and pumped through a heated PTFE tube to provide a solution of diisocyanate, which is immediately quenched in aqueous HCl to provide the diamine HCl salt (4). See “results and discussion section” on p. 20 to the end of the first paragraph of p. 21.
Sprecher teaches another embodiment which follows Scheme 2 on p. 21:
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. See p. 21 and discussion thereof. Compound (5) is an acyl hydrazide of claims 25-26, wherein R1 is an unsubstituted C6 aryl and compound (6) is an acyl azide of claims 25-26, wherein R1 is the same as above. Though Sprecher does not explicitly teach transforming compound (6) to the monoisocyanate of claims 24-26, wherein R1 is as above, this is the intended use of the disclosed process and it would be prima facie obvious to form the monoisocyanate from acyl azide (6). The system of Scheme 2 was set up to investigate a different, and more efficient, continuous liquid-liquid separation method to separate the aqueous phase from the organic phase using a more stable set of reactants (5) and (6) than that of the first reaction (2) and (3):
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See Figure 3 on p. 21 and discussion thereof. Thus, Sprecher teaches mixing aqueous NaNO2 and tert-butyl methyl ether (TBME, an organic extraction solvent of claim 3) to form a first solution, which is then reacted with an aqueous solution of the HCl salt of the acyl hydrazide (5) in mircroreactor (MR) to produce a mixture of acyl hydrazide (6), water, and TBME. The reaction between NaNO2 and HCl will form nitrous acid in situ, as evidenced by [0017] of the specification as filed. In this mixture, the acyl hydrazide (6) is more soluble in the toluene phase, and the organic and aqueous phases are separated from one another in a liquid-liquid phase separation unit (claim 58), which is further described in Fig. 4 on p. 21:
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. The phase separation unit included an impedance probe in connection with a position pump to regularly remove aqueous waste. The combined residence time in the MR and phase separation unit was about 1.5 min and the system was operated reliably for 3-4 hours. See discussion of Fig. 3 and 4 and Scheme 2 on p. 21.
Further regarding step (iii) of claims 1 and 57, both embodiments of Sprecher appear to meet the claimed limitations. In the first (Fig. 2), the residence time in the phase separation device is long (10 min), however, it still is a continuous process. Providing further support of this interpretation is that Sprecher specifies that the organic phase is continuously withdrawn. In the second (Fig. 3), though Sprecher does not explicitly teach the transformation of acyl azide (6) into its respect monoisocyanate, Sprecher clearly indicates that this is the intended use of the disclosed process. Therefore, it would be prima facie obvious to form the monoisocyanate from acyl azide (6) from a process which includes the more efficient continuous separation system of Figs 3 and 4.
Regarding step (iv) and claims 2 and 59, Sprecher teaches that the organic phase comprising the acyl azide (7) is further dried with sodium sulfate (Na2SO4), an anhydrous inorganic salt. See section 4.3.6 on p. 22. Also see MPEP 2144.04(V)(E).
Sprecher teaches that the use of flow chemistry to produce the disclosed compounds resulted in a process which was more efficient and safer than batchwise processes. Flow chemistry offers several advantages such as precise temperature control, minimized hold-up volume, rapid mixing, and efficient heat exchange. See “introduction section” on p. 20. In the abstract, Sprecher explicitly teaches that the disclosed process “safely provides multi-100g quantities of a labile diacyl azide (3)” (claim 28). Therefore, the process of Sprecher should also be capable of producing even larger quantities if scaled up, such as those in instant claims 60 and 61. Also see MPEP 2144.05 and MPEP 2144.04(IV)(A). Additionally, it is prima facie obvious to repeat and/or optimize a reaction until a desired amount of product is obtained. Also see conclusion section 3.
Rumi teaches an analogous synthesis which comprises continuously transforming an acyl hydrazide to an acyl azide in the presence of nitrous acid in a flow reactor. See abstract. Rumi teaches the process encompasses the following steps:
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. See p. 748 and experimental section on p. 749-750. Rumi teaches that the reaction between acyl hydrazide (2), HCl, and aqueous nitrous acid (HNO2) in steps b) and c) is carried out in the absence of an organic solvent. Rumi teaches that that acyl azide (3) can be extracted with organic solvents (DCM/EtOH) after the reaction is completed.
Balci is a review directed toward products that can be obtained from acyl azides, including isocyanates. See abstract and introduction section. The various rearrangement reactions of acyl azides are summarized in Scheme 2 on p. 1373:
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. Balci teaches that “The Schmidt reaction is the reaction of hydrazoic acid
with a carboxylic acid to form an acyl azide as the intermediate; by working under acidic conditions, the isocyanates are not isolated and undergo hydrolysis to produce the corresponding amine (Scheme 2).” Balci teaches “Among these, the Curtius rearrangement, which involves the reaction of an acyl azide to give an isocyanate, has been used extensively. Furthermore, the advantage of the Curtius rearrangement is the isolation of the acyl azide and, since no water is present to hydrolyze them to amines, the isolation of the isocyanate is easy. The process can also be induced by photolysis, but this pathway always gives rise to several side products in addition to the desired isocyanate.” See col. 1 on p. 1374. The mechanism for formation of isocyanates is also addressed in section 3 on p. 1376-1379. Thus, Balci teaches that it is well known in the art that if acyl azides are heated to decomposition in the absence of nucleophiles, such as water, then isocyanates are the expected product. Further, Balci teaches that the isolation of isocyanates is also easy because there is no water present.
Saito is directed toward a negative electrode which includes a solid electrolyte interface coating which contains a product with a crosslinked isocyanate group in an isocyanate compound. See abstract. Saito teaches that the following isocyanate compounds are desirable to produce the coating: 1-isocyanatohexane (the first option of claim 27, see [0059]), 1-isocyanatopentadecane (the second option in claim 27, see [0059]); 1-isocyanatoadmantane (the last option in claim 27, see [0065]); methylene bis(4,1-phenylene)diisocyanate (the third from final option of claim 23, see [0067]); and 1,3 and 1,4-phenylene diisocyanate (the middle two compounds in the second to last row of claim 23).
Britton is directed toward continuous flow systems for chemical synthesis. See abstract and introduction on p. 2423. Britton teaches that in-line (in flow) drying tubes, such as a molecular sieve column (claim 2), are known in the art and have been used in chemical synthesis flow systems. See Fig. 1a on p. 2423, Fig. 2 (step 51D) on p.2425, and first paragraph in col. 1 on p. 2425. Fig. 1a also includes an in-line liquid-liquid separator (claim 58).
Ascertainment of the Difference Between Scope of the Prior Art and the Claims (MPEP §2141.02-03)
Regarding claim 1, Sprecher does not explicitly teach: carrying out the reaction of step (i) in the absence of the organic solvent and adding said organic solvent to the claimed first solution to produce the claimed second solution in step (ii); step (iv) of drying the third solution in flow to remove residual water from the third solution; and step (vi) isolating the isocyanate.
Regarding claim 57, Sprecher does not explicitly teach that an aqueous solution comprising nitrous acid (HNO2) is mixed with the solvent (toluene) in flow to form a first solution; step (iv) of drying the third solution in flow to remove residual water from the third solution; and step (vi) isolating the isocyanate.
Finding of Prima Facie Obviousness Rationale and Motivation (MPEP §2142-2143)
It would have been prima facie obvious to one of ordinary skill in the art to combine the teachings of Sprecher, Rumi, Balci, Saito, and Britton to arrive at the instantly claimed processes with a reasonable expectation of success before the effective filing date of the claimed invention.
A person of ordinary skill would have been motivated to modify the order of addition of the reactants in the process disclosed in Figures 2 and 3 of Sprecher to arrive at the processes of instant claim 1 because Sprecher teaches that the organic solvent (toluene or TBME) is only included as an extraction agent for the acyl azide. See col. 2 of p. 20. Therefore, it would not be required to produce the acyl azide from the acyl hydrazide and leaving it out of the first step would still predictably produce acyl azide in an aqueous solution. Further, the selection of any order of performing process steps is prima facie obvious in the absence of new or unexpected results. See In re Burhans, 154 F.2d 690, 69 USPQ 330 (CCPA 1946) and MPEP 2144.04 (IV)(C). Alternatively, Rumi is also cited to provide further evidence that the transformation of an acyl hydrazide to an acyl azide in the presence of aqueous nitrous acid can be predictably carried out in the absence of an organic solvent.
A person of ordinary skill in the art would have been motivated to modify the order of addition of the reactants in the process disclosed in Figures 2 and 3 of Sprecher to arrive at the processes of instant claim 57 because the selection of any order of performing process steps is prima facie obvious in the absence of new or unexpected results. See In re Burhans, 154 F.2d 690, 69 USPQ 330 (CCPA 1946) and MPEP 2144.04 (IV)(C). As taught by Sprecher, the acyl hydrazide will not undergo the transformation until nitrous acid is generated and that the organic solvent is only present to extract the acyl azide from the reaction mixture. Sprecher further teaches that the HCl salts of the hydrazides were used, rather than the basic acyl hydrazides, because they are commercially available and soluble in water. See last paragraph in section 1 on p. 20. Therefore, if the HCl and NaNO2 were mixed prior to being contacted with the organic solvent, the skilled artisan would still predictably expect the mixture to produce the desired acyl azide when contacted with the acyl hydrazide.
A person of ordinary skill would have been motivated to modify the process of Sprecher/Rumi to produce and isolate isocyanates because Balci and Saito teach the production and isolation of isocyanates, with Saito explicitly teaching the utility of the claimed isocyanates. Thus, the references establish motivation for obtaining isocyanate products, which are known intermediates in the process of Sprecher/Rumi, and it is prima facie obvious to use a predictable process and apparatus to obtain and isolate a desired product which is already shown to be present in said process and apparatus.
A person of ordinary skill would have been motivated to modify the process of Sprecher, Rumi, Balci, and Saito to fully remove residual water from the acyl hydrazide solution prior to producing the isocyanate because Balci further teaches that water, and any other nucleophiles, should predictably be removed from the acyl azide prior to thermal decomposition according to the Curtius rearrangement to predictably produce isocyanates from acyl azides. Further, Britton is cited to explicitly teach that in-line (in flow) removal of water from solutions is known in the art and predictable and Sprecher teaches that acyl azide (7) is stable to treatment with a drying agent (Na2SO4). Therefore, if the process of Sprecher and Rumi were modified to produce isocyanates, as motivated by Saito and Balci, then it would be prima facie obvious to include an extra drying step in the process of Sprecher and Rumi to predictably increase the yield of the desired isocyanate process by eliminating water as taught by Balci, with Britton establishing that in line drying tubes are well-known in the art. The combination of the references renders the instantly claimed processes prima facie obvious and predictable. Also see MPEP 2143(I)(A) and (B).
Regarding claims 2 and 59, Sprecher teaches that acyl azide (7) is stable to treatment with a drying agent (Na2SO4) and Britton teaches in line drying tubes, including a molecular sieve tube. It would be prima facie obvious to replace one known drying agent for another in the tube to predictably fully dry the acyl azide in flow before isocyanate formation. Also see MPEP 2143(I)(B).
Regarding claims 4 and 5, Sprecher teaches in the experimental section 4.2, that 2.548 mol of dihydrazide (2 in Scheme 1) is contacted with 5.701 mol of NaNO2 in the presence of excess aqueous HCl. Assuming that 100% of the NaNO2 is transformed to HNO2, the molar ratio of acyl hydrazide : nitrous acid is 2.548 : 5.701 or 1 : 2.2, which is about 1 : 2. Sprecher also teaches in the experimental section 4.3, that the molar ratio of acyl hydrazide (6 in Scheme 2) : nitrous acid is 0.735 : 0.940, or about 1 : 1.3. Also see MPEP 2144.05 and [0073] of the specification as filed.
Regarding claims 6 and 7, in the experimental section 4.2, Sprecher teaches that the flow rate of solution A (water, HCl, and acyl dihydrazide 2) is 12.00 mL/min; the flow rate of solution B (NaNO2 and water) is 11.16 mL/min; and that the flow rate of solution C (toluene) is 16 mL/min. The instant first solution is analogous to the combined volume of solution A and B of Sprecher (11.16 + 12 = 23.16). Therefore, the volume ratio of toluene : the first solution is about 16 : 23 or about 1:1.4. Sprecher also teaches in the experimental section 4.3, that the flow rate of solution A is 10 mL/min; the flow rate of solution B is 3.8 mL; and the flow rate of solution C is 5.0 mL/min. Therefore, the volume ratio of organic solvent : the first solution is about 5 : 13.8 or about 1:2.8. The ratio of example 4.2 falls within the claimed range of claim 6 and just outside the range of claim 7. However, Sprecher teaches that neither of the disclosed processes is optimized and indicates that there is room for improvement in terms of yield and output. See conclusion section 3. Therefore, it would be prima facie obvious for the skilled artisan to vary factors such as flow rate and concentration in order to arrive at the instantly claimed process with a reasonable expectation of success. Also see MPEP 2144.05.
Regarding claims 8 and 9, Sprecher teaches that microreactors (MR) are run at 20°C or 0°C. See figures 2 and 3. The reaction at 20°C falls within the ranges of claims 8 and 9. Also see MPEP 2144.05.
Regarding claim 10, Sprecher teaches that the heating of the acyl azide is conducted at 100°C in the PTFE tube of Fig. 2. Also see MPEP 2144.05.
Response to Arguments on p. 7-11 of the 12/8/2025 response:
The Applicant amended the independent claims 1 and 57 such that step (iv) requires drying the third solution in flow to remove residual water from the third solution and such that the isocyanate is isolated in step (vi). The Applicant argues that the neither Sprecher nor Rumi provides motivation to isolate an isocyanate from the process of Sprecher. The Applicant additionally argues that such a modification to Sprecher’s reaction would render the reaction unsatisfactory for its intended purpose of making a racemic diamine.
This argument has been fully considered but is not persuasive. Though the Examiner maintains that a person of ordinary skill would have recognized that isocyanate production is another benefit to the apparatus of Sprecher based on Sprecher alone, the rejection was modified to include references which explicitly provide motivation as to why isocyanates should be produced and isolated. See discussions of Saito and Balci above. Further, the proposed modifications to the process of Sprecher to isolate isocyanate would not render the Sprecher reaction inoperable. Sprecher generally teaches that acyl azides are intermediates to a wide variety of industrially valuable chemicals, and that the publication is directed toward a more general synthesis and utilization of acyl azides in a flow apparatus. See abstract and introduction on p. 20. Therefore, Sprecher is not limited to the production of racemic diamines. Further, Sprecher explicitly teaches the production of isocyanates as an intermediate. Therefore, even if some of the isocyanate is dried and diverted to be isolated, some can still be reacted under acidic conditions to produce amines. The Examiner respectfully disagrees that Sprecher teaches that any modifications to the end use of the acyl azide renders the apparatus/process unsatisfactory for its intended purpose. Further Saito and Balci are newly cited to address the alleged deficiency of a lack of motivation to isolate isocyanates from the process of Sprecher.
The Applicant then acknowledges that instant step (iii) is taught by Sprecher, but argues that Sprecher does not teach claimed step (iv) to remove all residual water from the organic phase prior to heating the solution to produce the isocyanate (step v) and then isolate the isocyanate (step vi). The Applicant argues that step (iv) imparts criticality to the claimed process that is not reasonably suggested by Sprecher. The Applicant provides support with a “Second Declaration” filed under 37 CFR §1.132 on 12/8/2025 which teaches the following:
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It is noted that the 12/8/2025 declaration appears to be a more detailed version of the 9/12/2025 declaration which did not disclose the specific isocyanate being produced.
The Applicant’s arguments and evidence have been fully considered but are not persuasive. As suggested by Sprecher acyl azides, such as (7), can be isolated and dried with sodium sulfate (Na2SO4), an anhydrous inorganic salt. See section 4.3.6 on p. 22. Further, both embodiments of Sprecher indicate that the aqueous phase of the azide formation reaction is waste and is preferably discarded before the Curtius rearrangement. Further, it is well-known to those of ordinary skill in the art that water is undesirable in the Curtius rearrangement if isocyanate is the desired product because it can act as a nucleophile to the isocyanate as taught by newly cited Balci. Balci further teaches that if no water is present, that the isocyanate product of the Curtius rearrangement is easy to isolate. Britton is also newly cited to teach that removal of water in flow is known and can be carried out with an in-line drying tube. Thus, it is known that eliminating water from the acyl azide will increase the yield of isocyanate, and also provide the added benefit of simplifying the isolation of the desired isocyanate. Therefore, though the declaration shows that the yield of isocyanate increases when residual water is removed from the acyl azide, this effect is well-known and predictable. The resulting isocyanate would also predictably be purer than that obtained from a wet acyl azide because there are fewer side products being produced (such as the amines exemplified in Sprecher). Also see MPEP 716.
The Applicant further argues the alleged deficiencies of Sprecher and Rumi regarding a lack of motivation to modify the process to produce isocyanate and isolate it. This argument has been fully considered but is not persuasive. This argument was addressed above, and the rejection was modified to include new references which explicitly teach what can be inferred from Sprecher. Namely, that isocyanate is a desirable product which can be easily obtained by a modification of the process of Sprecher to dry the acyl azide before heating, which is a well known and predictable technique in the art as supported by Saito, Balci, and Britton. Also see MPEP 2143(I)(A) and MPEP 2143(I)(B).
Therefore, the claims remain rejected.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to AMY C BONAPARTE whose telephone number is (571)272-7307. The examiner can normally be reached 11-7.
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/AMY C BONAPARTE/ Primary Examiner, Art Unit 1692