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 (RCE) 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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 23 February 2026 has been entered.
Priority
This application is a 371 of PCT/KR2020/019185 which claims the benefit of KR 10-2020-0183547 and KR 10-2019-0176139 with an effective filing date of 27 December 2019 as reflected in the filing receipt mailed on 25 October 2022.
Status of the Claims
Claims 1-3, 5, 6, and 8 are pending.
Claim 1 is currently amended.
Claim 7 is currently cancelled.
Claim 4 was previously cancelled.
Terminal Disclaimer
As stated in the advisory action dated 04 February 2026, the terminal disclaimer filed on 23 January 2026 disclaiming the terminal portion of any patent granted on this application which would extend beyond the expiration date of US Application Number 17789407 has been reviewed and is accepted. The terminal disclaimer has been recorded.
Due to the recorded terminal disclaimer the nonstatutory double patenting rejections over the claims of copending Application No. 17789407 to Lee et al. (hereinafter Lee) are withdrawn.
Response to Amendments
Applicant’s amendments filed 23 February 2026 are acknowledged.
The current amendment filed on 23 February 2026 is non-compliant, see MPEP 714 II.F. The amendment filed after final on 23 January 2026 was not entered on the record. As a result, claim 1 has been amended without the proper mark-ups, see MPEP 714 II.C. The current amendments to claim 1 are interpreted as “wherein the hydrogen gas is supplied at a pressure of 50 to 220 bar, wherein the method is performed without an isomerization reaction step, and wherein the 1,4-cyclohexane dicarboxylic acid comprises 60wt% or more of trans isomers.”
Claim Rejections - 35 USC § 103
Applicant’s amendments to claim 1:
(1) adding the method is performed without an isomerization step are taught by both Qingcai and Choi; and,
(2) adding limitations of claim 7 to claim 1 regarding the trans % are taught by Qingcai and not by Choi.
Therefore, applicant’s amendment (2) to claim 1 is sufficient to overcome the rejections of:
Claims 1-3, 5, and 8 under 35 U.S.C. 103 as being unpatentable over Choi et al. (US 20170107164, hereinafter Choi);
Claim 6 under 35 U.S.C. 103 as being unpatentable over Choi et al. (US 20170107164, hereinafter Choi), as applied to the 35 USC 103 rejection of claims 1-3, 5, and 8 above, in view of Chen et al., (“High-Throughput Microporous Tube-in-Tube Microreactor as Novel Gas–Liquid Contactor: Mass Transfer Study”, 2011 January, AIChE Journal, Vol. 57, No. 1, Pgs. 239-249, hereinafter Chen); and,
Claim 7 under 35 U.S.C. 103 as being unpatentable over Choi et al. (US 20170107164, hereinafter Choi), as applied in the 35 USC 103 rejection of claims 1-3, 5, and 8 above, in view of Qingcai et al. (CN104549266, published 29 April 2015, see machine translation, hereinafter Qingcai).
Due to the amendment (2) to claim 1, the cancellation of claim 7, and the RCE filed on 23 February 2026, the rejections are withdrawn and a new ground(s) of rejection is/are provided below.
Applicant’s amendment (1) to claim 1 is not sufficient to overcome the rejections of:
Claims 1-3, 5, 7, and 8 under 35 U.S.C. 103 as being unpatentable over Qingcai et al. (CN104549266, published 29 April 2015, see machine translation, hereinafter Qingcai) in view of Choi et al. (US 20170107164, hereinafter Choi); and,
Claim 6 under 35 U.S.C. 103 as being unpatentable over Qingcai et al. (CN104549266, published 29 April 2015, see machine translation, hereinafter Qingcai) in view of Choi et al. (US 20170107164, hereinafter Choi), as applied to the 35 USC 103 rejection of claims 1-3, 5, 7, and 8 above, in further view of Chen et al., (“High-Throughput Microporous Tube-in-Tube Microreactor as Novel Gas–Liquid Contactor: Mass Transfer Study”, 2011 January, AIChE Journal, Vol. 57, No. 1, Pgs. 239-249, hereinafter Chen).
Due to the cancellation of claim 7 and the RCE filed on 23 February 2026, the rejections are withdrawn and a new ground(s) of rejection is/are provided below.
Response to Arguments
Applicant’s arguments filed 23 February 2026 have been fully considered but are moot due to the new grounds of rejection provided below.
Applicant argues that Qingcai, Choi, and Chen do not disclose the limitations as recited in newly amended claim 1. These arguments are moot because the new ground of rejection does not rely on the Qingcai and Choi references applied in the prior rejection of record for any teaching or matter specifically challenged in the argument
In response to applicant’s arguments on page 7 of the remarks filed on 23 February 2026, that “[b]y controlling the TPA concentration within the claimed range, claim 1 of the present application achieves a high trans-isomer content of 60% or more trans-CHDA even when using commonly available Pd/C catalyst.” It is noted that the instant claims do not specifically recite a technical effect related to the TPA concentrations and the specific Pd/C catalyst.
New Rejections Based on the RCE filed on 23 February 2026
Claim Objections
Claim 1 is newly objected to because of the following informalities:
Claim 1, line 8 states “1,4-cyclohexane dicarboxylic acid(CHDA)”, which appears to include a typographical mistake. The claim is interpreted to state “1,4-cyclohexane dicarboxylic acid (CHDA)”.
Claim 1, line 13 states “60wt%”, which appears to include a typographical mistake. The claim is interpreted to state “60 wt%”.
Appropriate correction is required.
In the Spirit of Compact Prosecution
While the examiner has attempted to identify all objections and clarity issues amongst the claims, applicant is advised that some objections and clarity issues may still remain. Going forward, the examiner respectfully requests applicant to perform a detailed review of the claims regarding clarity, grammar, antecedent basis, word spacing, and spelling issues.
Claim Rejections - 35 USC § 102
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claim 8 is newly rejected under 35 U.S.C. 102(a)(1) as being anticipated by Qingcai et al. (CN105582926, published 18 May 2016, hereinafter Qingcai ‘926).
Qingcai ‘926 is in the known prior art of “a hydrogenation catalyst of terephthalic acid and solves the problem of low selectivity of a catalyst on 1,4-cyclohexanedicarboxylic acid when terephthalic acid is subjected to hydrogenation to prepare the 1,4-cyclohexanedicarboxylic acid in the prior art”, see Abstract, thus; reducing the complexity and “energy consumption” of the process by eliminating the need for “isomerization of molten cis-1,4-cyclohexanedicarboxylic acid”, see Para. [0005].
Regarding instant application claim 8, Qingcai ‘926 discloses trans 1,4-cyclohexanedicarboxylic acid is known to be used in compositions, such as polyesters, coatings and drugs, see Paras. [0004]-[0005];[0026].
In regard to “prepared by the method of claim 1”, see MPEP 2113(I) stating “even though product-by-process claims are limited by and defined by the process, determination of patentability is based on the product itself. The patentability of a product does not depend on its method of production. If the product in the product-by-process claim is the same as or obvious from a product of the prior art, the claim is unpatentable even though the prior product was made by a different process.” In re Thorpe, 777 F.2d 695, 698, 227 USPQ 964, 966 (Fed. Cir. 1985) (citations omitted)”. Qingcai ‘926 discloses a composition comprising trans 1,4-cyclohexanedicarboxylic acid; therefore, the process of production is not given patentable weight.
Claim Rejections - 35 USC § 103
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.
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.
Claims 1-3 and 5 are newly rejected under 35 U.S.C. 103 as being unpatentable over Qingcai et al. (CN105582926, published 18 May 2016, hereinafter Qingcai ‘926).
Qingcai ‘926 is in the known prior art of “a hydrogenation catalyst of terephthalic acid and solves the problem of low selectivity of a catalyst on
1,4-cyclohexanedicarboxylic acid when terephthalic acid is subjected to hydrogenation to prepare the 1,4-cyclohexanedicarboxylic acid in the prior art”, see Abstract, thus; reducing the complexity and “energy consumption” of the process by eliminating the need for “isomerization of molten cis-1,4-cyclohexanedicarboxylic acid”, see Para. [0005].
Regarding instant application claim 1, Qingcai ‘926 teaches the “invention relates to a terephthalic acid hydrogenation catalyst, its preparation method, and a method for the catalytic hydrogenation of terephthalic acid to prepare 1,4-cyclohexanedicarboxylic acid” (CHDA), see Para. [0002], where “[d]ata from the specific implementation method shows that with a terephthalic acid concentration of 7.5 wt%, a catalyst-to-terephthalic acid mass ratio of 1:10, a reaction temperature of 230 ℃, a hydrogen pressure of 4 MPa, and a reaction time of 3 hours, the conversion rate of terephthalic acid is 100%, the selectivity for CHDA reaches 98%, and the selectivity for trans-CHDA is 85%, achieving good technical results and making it suitable for CHDA production”, see Paras. [0026];[0096], Table 1. Specifically, the single embodiment of Example 1, where “75 g of commercially available purified terephthalic acid was added to a high-pressure reactor, along with 7.5 g of the aforementioned Pd-Pt-Zn/TiO34-La35-O36 catalyst, and then 925 g of water. The mixture was stirred, and nitrogen gas was introduced three times for purging, followed by hydrogen gas three times for purging. Then, hydrogen gas was introduced to raise the hydrogen pressure to 4MPa and maintain it at a stable level. The reaction temperature was maintained at 230 ℃, and hydrogen gas was continuously introduced for 3 hours. After the reaction was completed, the reaction products were analyzed. For easy comparison, the analytical results are listed in Table 1.”, see Paras. [0026];[0029]-[0031];[0096], Table 1, specifically meeting in one express embodiment the method of preparing, supply acid, catalyst, and water, supply hydrogen gas, stirring during hydrogenation, within the range of terephthalic acid, i.e., 7.5 wt%, the products are analyzed directly after hydrogenation, i.e., no isomerization step, and within the trans 1,4-cyclohexanedicarboxylic acid range, i.e., 84 wt% trans-CHDA, in instant application claim 1; and,
The “hydrogen pressure is preferably 1-10 MPa” aka 10 to 100 bar, see Para. [0022], meeting within the pressure range in instant application claim 1.
In addition, the instant application claim 1 scope is not limited by claim language that suggests or makes optional but does not require steps to be performed, or by claim language that does not limit a claim to a particular structure, see MPEP 2111.04. In this case, the “wherein” clauses drawn to the terephthalic acid concentration and the trans isomer concentration appear to not give “meaning and purpose to the manipulative steps”, see MPEP 2111.04.
Regarding instant application claim 2, Qingcai ‘926 teaches “the concentration of terephthalic acid is preferably 1-20 wt%”, see Paras. [0023];[0031], meeting within the concentration of terephthalic acid in instant application claim 2.
Regarding instant application claim 3, Qingcai ‘926 teaches “the reaction temperature is preferably 160-260 ℃, more preferably 220-250℃”, specifically 230 ℃, see Paras. [0022];[0026];[0031], meeting within the temperature range in instant application claim 3.
Regarding instant application claim 5, Qingcai ‘926 teaches the catalyst specifically comprises Pd-Pt, see Para. [0021]-[0022];[0026];[0031], meeting the catalyst in instant application claim 5.
Qingcai ‘926 does not teach in one single express embodiment:
The instant application claim 1 pressure range; and,
The instant application claim 2 terephthalic acid concentration.
In reference to the above claims, it would have been obvious to one of ordinary
skill in the art, before the effective filing date of the claimed invention, to have modified the express embodiments of Qingcai ‘926 to use a pressure of 50 to 220 bar and 12 to 22 wt% of terephthalic acid in water, see MPEP 2144.05, with a reasonable predictability of success for the purpose of efficiently producing trans 1,4-CHDA by eliminating the need for a separate “isomerization of molten cis-1,4-cyclohexanedicarboxylic acid” step; thus, reducing the complexity and “energy consumption” of the process, see Paras. [0005];[0026];[0031];[0096]; Table 1.
Since “a prima facie case of obviousness exists” where the claimed ranges “overlap or lie inside ranges disclosed by the prior art” and where the claimed ranges or amounts do not overlap with the prior art but are merely close, see MPEP 2144.05, one of ordinary skill in the art, before the effective filing date of the claimed invention, would be able to predictably determine the optimal hydrogen pressure and terephthalic acid concentration by relying upon Paras. [0022]-[0023] of Qingcai ‘926 for the benefit of optimizing reaction conditions in order to produce 1,4-CHDA in high yield, see Paras. [0021]-[0023];[0026];[0096], Table 1.
“The normal desire of scientists or artisans to improve upon what is
already generally known provides the motivation to determine where in a disclosed set
of percentage ranges”, such as the concentration of the reactants, “is the optimum combination of percentages.” In re Hoeschele, 406 F.2d 1403, 160 USPQ 809 (CCPA 1969), see MPEP 2144.05.
In addition, “[i]t is a settled principle of law that a mere carrying forward of an original patented conception involving only change of form, proportions,” such as hydrogen gas pressure and terephthalic acid concentration, “or degree, or the substitution of equivalents doing the same thing as the original invention, by substantially the same means, is not such an invention as will sustain a patent, even though the changes of the kind may produce better results than prior inventions. In re Williams, 36 F.2d 436, 438, 4 USPQ 237 (CCPA 1929)”, see MPEP 2144.05.
Claims 1-3, 5, and 6 are newly rejected under 35 U.S.C. 103 as being unpatentable over Qingcai et al. (CN105582926, published 18 May 2016, hereinafter Qingcai ‘926), as applied to the 35 USC 103 rejection of claims 1-3 and 5 above, in further view of Chen et al., (“High-Throughput Microporous Tube-in-Tube Microreactor as Novel Gas–Liquid Contactor: Mass Transfer Study”, published January 2011, AIChE Journal, Vol. 57, No. 1, Pgs. 239-249, hereinafter Chen).
Qingcai ‘926 teaches the method for preparing trans 1,4-cyclohexane dicarboxylic acid according to instant application claim 1, see Paras. [0021]-[0022];[0026];[0031].
Qingcai ‘926 does not teach the instant application claim 6 limitations of wherein the stirring is conducted such that a surface area per unit volume of hydrogen gas bubbles becomes 15 m2/m3 or more.
Chen is in the known prior art field of gas-liquid contacting reactors, such as “gas–liquid catalytic hydrogenation” reactors, see Abstract; Pg. 240, Col. 1, Second Full Para.
Regarding instant application claim 6, Chen teaches by agitation/stirring “gas–liquid mass transfer rates are greatly increased, which can benefit such applications as gas absorption, gas–liquid catalytic hydrogenation … The gas flowing outward radially through the annular micropores is dispersed into annular gas streams (gas bubbles) and then impinges crosscurrently at high speed with the axial flow of the liquid in the chamber between the inner and outer tubes, thereby it will exhibit enhanced gas–liquid mass transfer efficiency and large throughput capacity”, see Pg. 240, Col. 1, Second Full Para.-Last Para., where “Table 1 gives a comparison of the liquid side volumetric mass transfer coefficient kLα and the measured interfacial area α of the MTMCR with those of other typical gas–liquid contactors used in the laboratories and industries reported”, such as a stirred tank reactor at 75 to 170 m2/m3, see Pg. 247, Col. 1, Comparison of liquid side volumetric mass transfer coefficient and interfacial area in different gas–liquid reactors, Table 1 and below,
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Therefore, it would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to have modified the stirring conditions of Qingcai ‘926 with the bubble generation interfacial area for hydrogen gas liquid contact teachings of Chen with a reasonable predictability of success for the purpose of maintaining optimal gas-liquid mass transfer rates by determining the correct proportion of raw material and hydrogen contact needed while limiting the formation of resultant isomers and by-products, see Chen, Pg. 240, Col. 1, Second Full Para.-Last Para.; Pg. 247, Col. 1, Table 1.
It would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to have modified the stirring conditions of Qingcai ‘926 by applying “routine optimization” and “predictable results” to select the optimal gas liquid contact conditions, as taught by Chen. One of ordinary skill in the art would have been motivated to make these modifications because Chen provides a finite number of identified, predictable solutions, and a person of ordinary skill in the art has good reason to select the appropriate methods depending on the nature of the materials to be synthesized by pursuing the known options within their technical grasp, such as determining the correct proportion of raw material and hydrogen contact needed while limiting the formation of resultant isomers and by-products produced, see Chen, Pg. 240, Col. 1, Second Para.-Last Para.; Pg. 247, Col. 1, Table 1 and MPEP 2141.
As stated in Sakraida v. Ag Pro, Inc., 425 U.S. 273, 189 USPQ 449, reh’g denied, 426 U.S. 955 (1976), “[w]hen a work is available in one field of endeavor, design incentives and other market forces can prompt variations of it, either in the same field or a different one. If a person of ordinary skill can implement a predictable variation, § 103 likely bars its patentability. For the same reason, if a technique has been used to improve one device, and a person of ordinary skill in the art would recognize that it would improve similar devices in the same way, using the technique is obvious unless its actual application is beyond his or her skill”, see MPEP 2141.
Further, In re Williams, 36 F.2d 436, 438, 4 USPQ 237 (CCPA 1929) states “[i]t is a settled principle of law that a mere carrying forward of an original patented conception involving only change of form, proportions, or degree,” such as stirring/agitation rate, “or the substitution of equivalents doing the same thing as the original invention, by substantially the same means, is not such an invention as will sustain a patent, even though the changes of the kind may produce better results than prior inventions”.
Conclusion
No claims are allowed.
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/YO/Examiner, Art Unit 1692
/FEREYDOUN G SAJJADI/Supervisory Patent Examiner, Art Unit 1699