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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 2/5/2026 has been entered.
Claim Status
Claims 1 and 9 were amended and claim 5 was canceled in the response filed 2/5/2026. Claims 1, 3, 4, 6-12 are pending and under examination.
Objections
The amendments filed on 2/5/2026 are persuasive to overcome the objection to the specification and the objection to claim 1 on p. 2-3 of the OA dated 11/5/2025. Therefore, the objections are withdrawn.
Claim 1 is newly objected to because of the following informalities:
In the final line of step (S2) in claim 1, the words “comparing” and “and” should be switched. It currently reads “comparing and” and should be amended to recite “and comparing”. Appropriate correction is required.
Withdrawn Claim Rejections - 35 USC § 101
The amendments to claim 1 filed 2/5/2026 are persuasive to overcome the statutory double patenting rejection over claim 2 of co-pending US app. no. 18/825290 on p. 3-4 of the OA dated 11/5/2025. Therefore, the rejection is withdrawn.
Double Patenting
See p. 4-6 of the OA dated 11/5/2025 for the rejection of record.
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claims 1, 3, 4, and 6-12 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-12 of co-pending Application No. 18/825290 (‘290, reference application).
Although the claims at issue are not identical, they are not patentably distinct from each other because claims 1 and 5 of ‘290 teach all the limitations of instant claim 1. Further, instant claims 3, 4, and 6-12 are identical to those in ‘290.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
On p. 7 of the response filed 2/5/2026, the Applicant indicates that that the provisional rejection will be addressed upon indication that the claims are otherwise allowable.
Withdrawn Claim Rejections - 35 USC § 112
The amendments filed on 2/5/2026 are persuasive to overcome the 35 USC 112(a) and 112(b) rejections of record on p. 6-10 of the OA dated 11/5/2025. The Applicant corrected the dependency of claim 9 and deleted the new matter from claim 1. Also see p. 7-8 of the 2/5/2026 response. Therefore, the rejections are withdrawn.
Claim Rejections - 35 USC § 103
The Applicant canceled claim 5 and incorporated its limitations into independent claim 1 in the 2/5/2026 response. The Applicant also deleted all of the equations from claim 1. Therefore, the rejection of record on p. 10-18 of the OA dated 11/5/2025 was modified to address the amendments.
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.
Claim(s) 1, 3, 4, and 6-12 is/are rejected under 35 U.S.C. 103 as being unpatentable over Kim (KR101663586B1, published on 10/10/2016, of record in the IDS filed on 2/28/2022) in view of Yang (US 2014/0288325, published on 9/25/2014, of record in the IDS filed on 12/1/2022) and as evidenced by Extended European Search Report (issued in corresponding European Patent Application No. 21818350.7 dated September 19, 2022, of record in the IDS filed on 12/1/2022).
Kim is not in English and there is no English language equivalent available, therefore two machine generated English language translations are also provided, one from Espacenet and one from Google Patents. All of the citations below correspond to the Espacenet translation unless explicitly told otherwise.
Applicant Claims
Applicant claims a method for controlling a reaction in a continuous production process of a diester-based composition in which a dicarboxylic acid and an alcohol react to produce the diester-based composition, comprising:
(S1) monitoring a feed flow rate of the dicarboxylic acid and the alcohol which are introduced into a reactor and a flow rate of product water which is generated in the reactor;
(S2) calculating a predicted conversion from the feed flow rate, the flow rate of the product water, and pressure and temperature in the reactor; and
(S3) controlling the temperature and the pressure of the reactor such that the calculated predicted conversion rate becomes closer to a target conversion rate,
wherein a molar ratio of the dicarboxylic acid and the alcohol in a feed introduced into the reactor is 1: 1.5 to 1: 4 (previously in claim 5).
Determining the Scope and Content of the Prior Art (MPEP §2141.01)
Kim discloses “a manufacturing method of dioctylterephthalate (DOTP-[0002]) having low consumption of reaction energy. The manufacturing method of dioctylterephthalate comprises: a first reaction step having a plurality of reactors; and a second reaction step having a reaction temperature lower than the reaction temperature in the last reactor during the first reaction step. According to the present invention, a reaction conversion rate is at least 99.9%, and uniformity in the quality of products is achieved.” See abstract. In claims 1-2, Kim teaches that terephthalic acid, a dicarboxylic acid of claim 11, is continuously reacted with octanol, A C8 alcohol of claim 12, in the presence of a catalyst to produce a DOTP diester based composition. Kim teaches that the reaction can be carried out in a series of reactors (claim 6). See claim 8, [0016], [0022], and [0051].
Kim teaches that the di-esterification reaction is controlled by temperature to increase the conversion rate. See claims and [0011-0012, 0016-0019, 0059]. Kim teaches that the reaction is monitored by “emission of the inputs and the product of the raw material”. See [0018]. Kim teaches that this includes monitoring, and if necessary, adjusting, the flow rate of the raw materials and product flow to alter the average reaction time in each reactor. Kim teaches in the examples that the reaction conversion is monitored by following the acid value of the unreacted terephthalic acid. See [0072]. See [0062, 0066]. Kim also teaches that the reaction temperature, pressure or composition inside the reactor can be controlled by flowing an inert gas at the lower end of the reactor. See last two claims and [0028, 0034, 0037, 0043-0045]. Kim teaches that the disclosed process produces a uniform product at a high conversion rate of 99% or above, while also decreasing energy costs. See abstract and [0008-0010, 0028-0030, 0037-0038, 0065] and examples.
Kim also teaches that the reactors may comprise “can produce the removal equipment and the equipment selected from the condenser by evaporation of alcohol” in [0048]. Paragraph [0072] further teaches a “removal and recovery alcohol condensation cooling unit”. Since the quality of these sections of the translation in Espacenet are not clear, another translation was obtained from Google Patents.
In the Google Patents translation, [0048] recites: “Each reactor according to one embodiment of the present invention may include, in whole or in each case, a device selected from a heating device, a stirring device, a product water removing device and an evaporative alcohol condensing device.” See sixth from final paragraph on p. 3 of the translation, wherein the word “water” is bolded.
In the Google Patents translation, the first sentence of [0072] recites “A uniformly mixed feedstock is a first 2-liter reactor in a continuous 2-liter reactor equipped with an electrothermal heating device capable of controlling the reaction temperature, a paddle stirrer, a nitrogen feeder and a cooling device for removal of product water and recovery alcohol condensation.” See sixth paragraph from the top on p. 5, wherein the word “water” is bolded.
Further, the Extended European Search Report issued in corresponding European Patent Application No. 21818350.7 dated September 19, 2022, is also cited as an evidentiary reference to teach that this is an accurate translation of these sections of Kim. See section 2, paragraph bridging p. 2-3.
Therefore, Kim teaches that the di-esterification process produces water as a product, and that it is continuously removed from the reaction.
Regarding the molar ratio of dicarboxylic acid and the alcohol in the feed in claim 1, Kim teaches that the molar ratio of the dicarboxylic acid to the alcohol in each reactor is 1:1 to 1:8. See claim 9 and [0057 and 0062]. This range encompasses that claimed. Also see MPEP 2144.05.
Regarding claims 7 and 8, Kim teaches that the reaction temperature in each reactor is between about 180-270°C, preferably between 200-250°C, which encompasses the claimed ranges. See [0058-0059]. Also see MPEP 2144.05.
Regarding claims 9 and 10, Kim teaches that the reaction can be run at atmospheric pressure, in a vacuum, or under pressure. See claim 4 and [0020]. The example in [0072] teaches atmospheric pressure, which corresponds to about 1 kg/cm2. In [0074] a pressure of 700 torr is used, which corresponds to about 0.95 kg/cm2. In [0075] the pressure is 0.2 bar, which corresponds to about 0.2 kg/cm2. Therefore, the ranges taught by Kim encompass or overlap with those claimed. Also see MPEP 2144.05.
Yang teaches an analogous process to that of Kim for preparing di(2-ethylhexyl) terephthalate (DOTP). Yang teaches that the process comprises reacting terephthalic acid with 2-ethylhexanol in the presence of a catalyst in a reactor to produce DOTP and water. See abstract and claims. Yang teaches that a mixture of alcohol and water vapor from the reaction is condensed and separated in an oil-water separator. Yang teaches that the water is removed from the system to increase the conversion rate of the reversible esterification reaction, while the alcohol is returned to the reactor. Yang teaches that the conversion rate of the terephthalic acid can be calculated by measuring the water removed and by monitoring the molar ratio of alcohol to terephthalic acid in the reactor. See [0010 and 0019].
Ascertainment of the Difference Between Scope of the Prior Art and the Claims (MPEP §2141.02-03)
With regard to claims 1, 3, and 4, Kim does not explicitly teach that the flow rate of the water is monitored and, along with the flow rate of the raw materials, the pressure, and the temperature in each reactor, to calculate a predicted conversion rate in the reactor. Nor does Kim explicitly teach an additional monitoring step after a predicted conversion rate is calculated (claims 3 and 4).
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 Kim and Yang to arrive at the instantly claimed process 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 monitor the flow rate of the water exiting the reactor of Kim and calculate a predicted conversion because Yang suggests as much. Both Kim and Yang teach the benefits of monitoring and adjusting several reaction variables, including temperature, pressure, the flow rate of the raw materials and the flow rate of the products (including water) to control the reaction in each reactor to increase product conversion. Yang also suggests calculating a predicted conversion rate based on at least the concentrations of the raw materials in the reactor and the amount of water being removed from the reactor. The concentrations of the raw materials in a continuous process would be determined by their flow rate and the flow rate of the products, as discussed in Kim. The skilled artisan would also realize that the conversion rate would also be dependent on the pressure and temperature of the reaction, especially as the alcohol is volatile. Calculating a predicted conversion rate would predictably make the skilled artisan aware of how the reaction is performing in real time, which is desirable. A predicted conversion rate in real time would alert the skilled artisan to potential issues that can be corrected if the predicted conversion rate does not match the experimental conversion rate. Thus, using known variables to calculate predicted conversion rates is an example of routine and predictable process optimization. It would also be prima facie obvious for the skilled artisan to re-monitor the reaction in each reactor after any adjustments to ensure that the adjustment was beneficial, which renders the limitations of claims 3 and 4 prima facie obvious. Also see MPEP 2143(I)(A) and MPEP 2144.05.
Response to Applicant Arguments on p. 8 of the response filed 2/5/2025
The Applicant argues that the applied references, either alone or combination, fail to disclose or render obvious a molar ratio of the dicarboxylic acid and the alcohol in a feed introduced into the reactor of 1:1.5 to 1:4 as set forth in the claims.
This argument has been fully considered but is not persuasive. As discussed above, Kim teaches that the molar ratio of the dicarboxylic acid to the alcohol in each reactor is 1:1 to 1:8. See claim 9 and [0057 and 0062]. This range encompasses that claimed. Also see MPEP 2144.05.
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