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 .
Status of the Claims
Claims 1, 6-8, and 10 are pending.
Claim 1 is newly amended.
Claims 2-5 and 9 were previously cancelled.
Priority
This application is a 371 of PCT/KR2020/019186 which claims the benefit of KR 10-2020-0183549 and KR 10-2019-0176139 with an effective filing date of 27 December 2019 as reflected in the filing receipt mailed on 07 November 2022.
Information Disclosure Statement
The information disclosure statement (IDS) submitted on 12 December 2025 is in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statement has been considered by the examiner.
Response to Amendments
Applicant’s amendments filed 02 January 2026 are acknowledged.
Claim Objections
Applicant’s amendment to claim 1 is sufficient to overcome the objection of the claim. The claim has been amended to add “the steps”. The objection is withdrawn.
Claim Rejections - 35 USC § 102
The rejection of claim 10 under 35 U.S.C. 102(a)(1) as being anticipated by Hembre et al. (US20150183699, hereinafter Hembre) is maintained.
Claim Rejections - 35 USC § 103
Applicant’s amendments to claim 1 adding a gas-induced stirrer are not sufficient to overcome the rejection of claims 1, 6, and 7 under 35 U.S.C. 103 as being unpatentable over Hembre et al. (US20150183699, hereinafter Hembre) in view of Yoshiyuki et al. (JP2014177422, published 25 September 2014, see machine translation, hereinafter Yoshiyuki). The rejection is maintained; however, due solely to the amendment to claim 1 an additional modified new ground(s) of rejection is/are provided below.
Applicant’s amendments to claim 1 adding a gas-induced stirrer are not sufficient to overcome the rejection of claim 8 under 35 U.S.C. 103 as being unpatentable over Hembre et al. (US20150183699, hereinafter Hembre) in view of Yoshiyuki et al. (JP2014177422, published 25 September 2014, see machine translation, hereinafter Yoshiyuki), as applied to claims 1, 6, and 7 in the 35 USC 103 rejection above, in further view of Nieves-Remacha et al. (“Gas−Liquid Flow and Mass Transfer in an Advanced-Flow Reactor”, 30 May 2013, Industrial & Engineering Chemistry Research, Vol. 52, Pgs. 8996-9010, hereinafter Nieves-Remacha). The rejection is maintained; however, due solely to the amendment to claim 1 an additional modified new ground(s) of rejection is/are provided below.
Response to Arguments
Applicant’s arguments filed 02 January 2026 have been fully considered but they are either moot or not persuasive.
Applicant’s argue that Hembre, Yoshiyuki, and Nieves-Remacha do not disclose the limitations as recited in newly amended claim 1. These arguments have been considered but are moot because the new ground of rejections do not rely on any reference applied in the prior rejection of record for any teaching or matter specifically challenged in the argument.
In response to applicant’s argument on page 4 of the remarks filed on 02 January 2026 regarding the 35 USC 102(a)(1) rejection of claim 10 and “[c]laim 10 is patentable over the cited art at least by virtue of its dependency from claim 1.”
As stated on page 6 of the previous office action dated 01 October 2025:
“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)”. Hembre discloses a composition comprising 1,4-cyclohexanedimethanol and a product and it’s properties are inseparable, see MPEP 2112.01; therefore, the process of production is not given patentable weight.”
For the reasons indicated above, applicant’s above argument is not persuasive.
In response to applicant’s arguments on page 7 of the remarks filed on 02 January 2026 regarding “the gas-induced type stirrer comprises a gas inlet, a gas passage, and plural jet orifices” and the stirrers’ designed function, it is noted the above information regarding the gas-induced type stirrer and function are not instantly claimed. Although the claims are interpreted in light of the specification, limitations from the specification are not read into the claims, see In re Van Geuns, 988 F.2d 1181, 26 USPQ2d 1057 (Fed. Cir. 1993) and MPEP 2145 VI. For the reasons indicated above, applicant’s above arguments are not persuasive.
New, Maintained, and Modified Rejections Based on Amendments to the Claims in the reply filed on 02 January 2026
For clarity between the new, modified, and maintained rejections, the specific new and modified rejections are in italics.
New Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
Claims 1, 6-8, and 10 are newly rejected under 35 U.S.C. 112(b) as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor regards as the invention.
Regarding claim 1, the term “a gas-induced type stirrer” in claim 1 is a relative term which renders the claim indefinite. The addition of the word "type" to an otherwise definite expression (e.g., a gas-induced stirrer) extends the scope of the expression so as to render it indefinite, see MPEP 2173.05(b) III.A.E. The term “type” is not defined by the claim, the specification does not provide a standard for ascertaining the requisite degree, and one of ordinary skill in the art would not be reasonably apprised of the scope of the invention.
Claims 6-8 and 10 depend from base claim 1 and are included in this rejection as they do not correct the informalities identified in base claim 1.
In the Spirit of Compact Prosecution
Throughout prosecution 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.
Maintained 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 10 stands rejected under 35 U.S.C. 102(a)(1) as being anticipated by Hembre et al. (US20150183699, published 02 July 2015, hereinafter Hembre).
Hembre discloses the instant application claim 10 limitations of a composition comprising 1,4-cyclohexanedimethanol, such as stream 70 as a liquid overflow composition removed from second hydrogenation reactor 60 containing 1,4-cyclohexanedimethanol (CHDM) and ruthenium TRIPHOS dissolved in N-methyl-2-pyrrolidone, see Paras. [0002];[0061];[0069].
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)”. Hembre discloses a composition comprising 1,4-cyclohexanedimethanol and a product and it’s properties are inseparable, see MPEP 2112.01; therefore, the process of production is not given patentable weight.
New 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.
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.
Claims 1, 6, and 7 are newly rejected based on the amendments to claim 1 filed on 02 January 2026 under 35 U.S.C. 103 as being unpatentable over Hembre et al. (US20150183699, published 02 July 2015, hereinafter Hembre) in view of Yoshiyuki et al. (JP2014177422, published 25 September 2014, see machine translation, hereinafter Yoshiyuki), and in further view of Crezee et al. (“Three-phase hydrogenation of D-glucose over a carbon supported ruthenium catalyst—mass transfer and kinetics”, published 2003, Applied Catalysis A: General, Vol. 251, Pgs. 1-17, hereinafter Crezee).
Hembre teaches the claim 1 limitations of a method of producing at least one hydroxymethylcyclohexane, such as 1,4-cyclohexanedimethanol (CHDM), see Paras. [0002];[0008]-[0010], by supplying at least one cyclohexanecarboxylic acid, such as 1,4-cyclohexanedicarboxylic acid (CHDA), with hydrogen and an acid hydrogenation catalyst in a second reaction zone under second reaction conditions, such as continuous stirring, effective to hydrogenate the acid groups on at least some of the at least one cyclohexanecarboxylic acid to produce a second composition containing at least one hydroxymethylcyclohexane compound and the at least one solvent, see Paras. [0002];[0008]-[0010];[0052];[0095]-[0097], Table 12, where the cyclohexanecarboxylic diacid (CHDA) feed has a cis/trans ratio, see Para. [0040], the hydroxymethylcyclohexane (CHDM) produced from the cyclohexanecarboxylic diacid (CHDA) feed has a cis/trans ratio of from about 0.20 to about 5.00, see Paras. [0040];[0053]-[0054], as calculated by the examiner a ratio of about 0.20 equals 1 cis:5 trans or about 20% cis to about 80% trans and a ratio of about 5.00 equals 5 cis:1 trans or about 80% cis to about 20% trans, the solvent is water, see Para. [0027];[0095]-[0097], Table 12, and the acid hydrogenation catalyst contains a ruthenium compound, see Paras. [0017];[0043], meeting:
The supplying a reaction solution with cis and trans isomers, conducting the hydrogenation reaction under conditions of stirring, and preparing 1,4-cyclohexanedimethanol (CHDM) within the range of trans isomers in instant application claim 1; and,
The hydrogen gas is supplied to the hydrogen reactor at a pressure of 1,500-2,500 psig or 103-172 bar and the reaction is conducted at a temperature of from about 100 to about 250° C, see Paras. [0008]-[0010];[0019];[0051];[0061], meeting:
Supplying hydrogen, within the range of hydrogen gas pressure, and within the range of hydrogenation reactor temperature in instant application claim 1.
Hombre does not teach:
The instant application claim 1 limitations of wherein the 1,4-cyclohexane dicarboxylic acid (CHDA) comprising cis isomers and trans isomers is included in the amount of 10 to 23 wt%, based on a total weight of the 1,4-cyclohexane dicarboxylic acid and water and wherein the 1,4-cyclohexane dicarboxylic acid comprises 60 wt% or more of trans isomers; and,
The limitations of instant application claims 6 and 7.
Yoshiyuki relates to the hydrogenation of mostly trans 1,4-cyclohexane dicarboxylic acid, 1,4-CHDA, in the presence of a ruthenium and tin catalyst in an aqueous liquid phase to produce 1,4-cyclohexanedimethanol, 1,4-CHDM, with a trans content of 1 to 99 wt %, more preferably 5 to 80 wt %, and even more preferably 30 to 75 wt %, where the hydrogenation and isomerization reaction proceed simultaneously, see Paras. [0001];[0006];[0012];[0016];[0023];[0025];[0033]-[0034].
Yoshiyuki teaches the content of the trans isomer in the cycloalkanedicarboxylic acid, 1,4-CHDA, raw material is preferably 1 to 99 wt %, more preferably 5 to 80 wt %, the remaining weight percent is cis isomer, and when water is used as a solvent, it is preferably used so that the concentration of the raw material compounds before the reaction is 5 to 50% by weight, more preferably 10 to 40% by weight, see Paras. [0004];[0015];[0017], meeting and within the range limitations of trans isomer and cis isomer 1,4-CHDA and within the range of weight % 1,4-CHDA content in the raw material in instant application claim 1; and,
The hydrogenation catalyst includes ruthenium and tin, see Para. [0018], meeting the catalysts material limitations in instant application claim 6 and in instant application claim 7.
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 hydrogenation of Hembre to use the reactant concentrations and the specific catalysts as taught by Yoshiyuki with a reasonable predictability of success for the purpose of producing a high melting point polyester or polyesteramide as a derivative of 1,4-CHDM by producing high trans content 1,4-CHDM from a high trans content 1,4-CHDA, while using the optimal hydrogenation catalyst to promote the isomerization of cyclohexanedimethanol from the cis isomer to the trans isomer and suppress the isomerization of the trans isomer to the cis isomer, see Yoshiyuki, Paras. [0005]-[0006];[0025];[0028].
The rationale to support a conclusion that the claim would have been obvious is that “a person of ordinary skill has good reason to pursue the known options within his or her technical grasp. If this leads to the anticipated success, it is likely that product [was] not of innovation but of ordinary skill and common sense”, see MPEP 2143 I.E. Since both Hembre and Yoshiyuki teach producing 1,4-CHDM by the ruthenium catalyzed hydrogenation of 1,4-CHDA, a person of ordinary skill in the art has good reason to produce high trans content 1,4-CHDM by pursuing the known options within their technical grasp for the benefit of producing a high melting point polyester or polyesteramide as a derivative of 1,4-CHDM by producing high trans content 1,4-CHDM from a high trans content 1,4-CHDA, while using the optimal hydrogenation catalyst to promote the isomerization of cyclohexanedimethanol from the cis isomer to the trans isomer and suppress the isomerization of the trans isomer to the cis isomer, see Yoshiyuki, Paras. [0005]-[0006];[0025];[0028] and MPEP 2141.
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 reactant concentrations, temperatures, pressures, and cis/trans ratios, “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.
Selection of a known material, such as a ruthenium and tin catalyst and an aqueous solvent system, based on its suitability for its intended use supported a prima facie obviousness determination in Sinclair & Carroll Co. v. Interchemical Corp., 325 U.S. 327, 65 USPQ 297 (1945), see MPEP 2144.07.
Regarding newly amended instant application claim 1, Hombre teaches hydrogenation to produce hydroxymethylcyclohexane, such as 1,4-cyclohexanedicarboxylic acid (CHDM), is performed in a stirred autoclave on a carbon supported ruthenium catalysts, see Paras. [0002];[0061]-[0062];[0068]-[0070];[0095]-[0098].
Hombre does not teach the newly amended instant application claim 1 limitation of a gas-induced type stirrer.
Crezee is in the known prior art field of ruthenium on carbon catalytic hydrogenation reactions in an autoclave, see Abstract.
Regarding newly amended instant application claim 1, Crezee teaches the hydrogenation is performed in an “autoclave equipped with a gas-induced stirrer”, see Pg. 6, 2.2. Hydrogenation experiments; Pgs. 6-7, 3.1. Gas-liquid mass transfer coefficient, meeting the gas-induced stirrer reactor in instant application claim 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 stirrer of Hombre to use the gas-induced stirrer as taught by Crezee with a reasonable predictability of success for the purpose of efficiently controlling the hydrogen gas–liquid mass transfer coefficients in order to control the hydrogenation catalyst activity and the hydrogenation reaction rate, see Crezee, Abstract; Pgs. 6-9, 2.2. Hydrogenation experiments-3.3. Mass transfer limitation.
The rationale to support a conclusion that the claim would have been obvious is that “a person of ordinary skill has good reason to pursue the known options within his or her technical grasp. If this leads to the anticipated success, it is likely that product [was] not of innovation but of ordinary skill and common sense”, see MPEP 2143 I.E. Since patents are part of the literature of the prior art relevant for all they contain, see MPEP 2123, and both Hombre and Crezee teach ruthenium on carbon catalytic hydrogenation reactions in an autoclave in the catalytic hydrogenation industry, a person of ordinary skill in the art has good reason to modify the stirrer of Hombre by relying upon the gas-induced stirrer of Crezee before the effective filing date of the claimed invention for knowledge generally available within the stirrers for catalytic hydrogenation reactors art, see MPEP 2143 B & G and 2141, for the benefit of efficiently controlling the hydrogen gas–liquid mass transfer coefficients in order to control the hydrogenation catalyst activity and the hydrogenation reaction rate, see Crezee, Abstract; Pgs. 6-9, 2.2. Hydrogenation experiments-3.3. Mass transfer limitation; 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.
Claims 1, 6, 7, and 8 are newly rejected based on the amendments to claim 1 filed on 02 January 2026 under 35 U.S.C. 103 as being unpatentable over Hembre et al. (US20150183699, published 02 July 2015, hereinafter Hembre) in view of Yoshiyuki et al. (JP2014177422, published 25 September 2014, see machine translation, hereinafter Yoshiyuki), and in further view of Crezee et al. (“Three-phase hydrogenation of D-glucose over a carbon supported ruthenium catalyst—mass transfer and kinetics”, published 2003, Applied Catalysis A: General, Vol. 251, Pgs. 1-17, hereinafter Crezee), as applied to claims 1, 6, and 7 in the 35 USC 103 rejection above, in further view of Nieves-Remacha et al. (“Gas−Liquid Flow and Mass Transfer in an Advanced-Flow Reactor”, 30 May 2013, Industrial & Engineering Chemistry Research, Vol. 52, Pgs. 8996-9010, hereinafter Nieves-Remacha).
Hembre teaches feeding hydrogen into the reactor at a pressure of 1500 psig under an agitation of 1000 rpm and maintaining this pressurized feed and agitation for 10 hours, see Paras. [0061];[0070], meeting the stirring and hydrogen gas in instant application claim 8.
Hembre does not teach the instant application claim 8 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.
Nieves-Remacha relating to bubble generating systems of gas-liquid contacting reactors, such as bubble columns with interfacial areas of 50−600 m2/m3, see Abstract, teaches in stirred reactors the bubble size distribution depends on the agitation speed, the design and type of impeller, and the physical properties of the fluids, see Pg. 8999, Col. 1, First Full Para., where stirred tank reactors have interfacial areas of 100−2000 m2/m3, see Pg. 9007, Col. 1 and Pg. 9008, Table 2, meeting the stirring to obtain a surface area per unit volume of gas bubbles of 15 m2/m3 or more in instant application claim 8.
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 reactor stirring of Hembre with the stirred reactor bubble generation teachings of Nieves-Remacha with a reasonable predictability of success for the purpose of optimizing the reaction speed, efficiency, and conversion by optimizing the mass transfer rate between the liquid and gas phases while minimizing power consumption, see Nieves-Remacha, Pg. 9007, Col. 1-Pg. 9008, Col. 2 and Table 2.
By applying “routine optimization” and “predictable results” to select the optimal
agitation for gas bubble liquid contact reactions, one of ordinary skill in the art would have been motivated to make these modifications because Nieves-Remacha provides a finite number of identified, predictable solutions. A person of ordinary skill in the art has good reason to efficiently conduct a gas-liquid reaction by pursuing the known options within their technical grasp for the benefit of optimizing the reaction speed, efficiency, and conversion by optimizing the mass transfer rate between the liquid and gas phases while minimizing power consumption, see Nieves-Remacha, Pg. 9007, Col. 1-Pg. 9008, Col. 2, Table 2, 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.
In addition, “[t]he 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 stirring rate as it relates to surface area per unit volume of hydrogen gas bubbles, “is the optimum combination of percentages.” In re Hoeschele, 406 F.2d 1403, 160 USPQ 809 (CCPA 1969), see MPEP 2144.05.
Conclusion
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL, see MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Y. Lynnette Kelly-O'Neill whose telephone number is (571) 270-3456. The examiner can normally be reached Monday-Thursday, 8 a.m. - 6 p.m., EST, with Flex Time.
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/YO/Examiner, Art Unit 1692
/FEREYDOUN G SAJJADI/Supervisory Patent Examiner, Art Unit 1699