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and the fee set forth in 37 CFR 1.1 7(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 04/17/2026 has been entered.
Status of Claims
Claims 1, 12, 21, 22, 23, 24 and 27 have been amended. Claims 4-5, 13 and 15-20 and 25-26 have been cancelled. New claims 28-31have been added. Claims 1-3, 6-12, 14 and 21-24 and 27-31 are pending. In view of the amendments to claims 24 and 27, which are amended as dependent claims of claim 1, both claims 24 and 27 are rejoined and examined herein. Claims 1-3, 6-12, 14 and 21-24 and 27-31 are examined herein.
Response to Amendments
The Amendments to the Claims filed 04/17/2026 have been entered. The minor informalities have been addressed by amendments and objections to claim 1 thereto are withdrawn accordingly. The previous 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph rejections of claims 1-4, 6-12, 14 and 21-23 are withdrawn in view of the Applicant's amendments and arguments.
Response to Arguments
Applicant's Remarks/Arguments and Amendments to the Claims both filed 04/17/2026 and Applicant's Remarks/Arguments filed 04/17/2026 have been fully considered. It is noted that the claim 1, an independent claim from which all of the claims ultimately depend, has been amended to recite “wherein the extraction solvent comprises a polar organic extraction solvent immiscible in the synthetic feedstock, further wherein the extraction solvent comprises diethylene glycol monobutyl ether, ethylene glycol monobutyl ether, diethylene glycol,
Applicant argues that the claim 1 as amended and its dependent claims, are not anticipated or prima facie obvious over cited prior arts, Zhang et al (WO 2020/178599 A1) and/or Van Der Reed et al (2018/0010050 A1). Applicant argues that claim 1 is currently amended to specify that the extraction solvent comprises diethylene glycol monobutyl ether, ethylene glycol monobutyl ether, diethylene glycol, or any combination thereof. Various ether alcohols are recited in claims 23, 24, and 27. The cited prior art does not teach or suggest any of the claimed extraction solvents. See Remarks filed 04/17/2026, pages 7-8.
In response, the arguments are directed to the amended claim limitations. Therefore, the arguments are considered moot.
Upon further consideration and search, a modified/new ground of rejections to claims 1-3, 6-12, 14 and 21-24 and 27-31 are presented in view of the previously found references as presented in the instant Office action.
MODIFIED REJECTIONS
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.
Claim(s) 1-3, 6-12, 14 and 23 is/are rejected under 35 U.S.C. 103 as being unpatentable over Zhang et al (WO 2020/178599 A1, hereinafter “Zhang”), in view of Usman et al. (ASPEN plus simulation of liquid–liquid equilibria data for the extraction of aromatics from waste tyre pyrolysis gasoline using organic and deep eutectic solvents: a comparative study, Applied Petrochemical Research (2021) 11:113–122, hereinafter “Usman”).
In regard to claims 1 and 23, Zhang discloses a process of upgrading a pyrolysis oil derived from the pyrolysis of plastic comprising adding a polar organic upgrading solvent immiscible in the pyrolysis oil to produce an extract phase and a raffinate phase. These immiscible phases are separated to yield an upgraded pyrolysis oil product (the abstract, paragraphs 0058, 0075, 0079, 0096).
Zhang discloses the polar organic upgrading solvent (i.e., an extraction solvent) comprises acetone (paragraph 00140), and/or diethylenetriamine (paragraph 00146).
But Zhang does not disclose the extraction solvent comprise diethylene glycol monobutyl ether, ethylene glycol monobutyl ether, diethylene glycol, or any combination thereof.
However, Usman discloses a method of extracting useful chemicals such as benzene, toluene and xylenes (BTX) from waste tyre pyrolysis gasoline (WTPG) (plastic pyrolysis oil) using organic solvents such as diethylene glycol (DEG) (page 113, Abstract; page 120, Conclusion).
It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to have modified the Zhang process to provide the extraction solvent comprise diethylene glycol as taught by Usman to arrive at the applicants’ claimed process.
In regard to claim 2, Zhang discloses the synthetic feedstock composition comprises a pyrolysis oil (paragraph 0057).
In regard to claims 3 and 14, Zhang discloses the pyrolysis oil is a derived from the pyrolysis of plastic or rubber, or a combination thereof (paragraph 0057).
Zhang does not disclose the synthetic feedstock comprising components as recited in claim 3 or the process of obtaining the synthetic feedstock as recited in claim 14. However, it is known that the components in the produce plastic-derived pyrolysis oil depends on the conditions of the pyrolysis condition (0052 of the specification of the application), and Zhang discloses the pyrolysis oil is a derived from the pyrolysis of plastic or rubber, or a combination thereof (paragraph 0057).
It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to have modified the Zhang process by selecting appropriate conditions of the pyrolysis to produce a pyrolysis oil having components as recited in claims 3 and 14 to arrive at the applicants’ claimed process except the criticality can be shown by applicants.
Regarding claim 6, Zhang discloses the upgrading solvent comprising about 90% NMP and about 10% water (paragraph 0172).
Regarding claim 7, Zhang discloses the mass ratio of synthetic feedstock to extraction solvent is about 95:5 to about 10:90. (paragraph 0078).
Regarding claim 8 and 9, Zhang does not disclose specifically where or when the upgrading solvent is added to the pyrolysis oil.
It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to have modified the Zhang process to add the solvent to where and/or when the upgrading process is needed to arrive at the applicants’ process except the criticality can be shown by applicants.
Regarding claim 10, Zhang discloses the upgrading solvent is added in ppm as recited in the claim.
It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to have modified the Zhang process by adding appropriate ppm of solvent to the pyrolysis oil to arrive at the applicants’ claimed process except the criticality can be shown by applicants.
Regarding claims 11 and 12, Zhang discloses the pyrolysis oil contains unwanted substances which are removed during upgrading step. One of them is olefins (paragraphs 0061, 0062, 0081, 0111).
Claim(s) 21 is/are rejected under 35 U.S.C. 103 as being unpatentable over Zhang et al (WO 2020/178599 A1) in view of Chen (Translation of CN 106118706 A) and Usman et al. (ASPEN plus simulation of liquid–liquid equilibria data for the extraction of aromatics from waste tyre pyrolysis gasoline using organic and deep eutectic solvents: a comparative study, Applied Petrochemical Research (2021) 11:113–122, hereinafter “Usman”).
Zhang discloses a process a discussed above.
But Zhang does not discloses: (I) adding a pour point depressant to pyrolysis product; and (II) the extraction solvent comprise diethylene glycol monobutyl ether, ethylene glycol monobutyl ether, diethylene glycol, or any combination thereof.
However, regarding (I), Chen discloses adding pour point depressant to the waste biomass oil. It is noted herein that the pour point depressant was added to organic phase containing long chain alkane rich in hydrocarbon, not to the biomass (see claim 1-step (6) in English translation document).
Regarding (II), Usman discloses a method of extracting useful chemicals such as benzene, toluene and xylenes (BTX) from waste tyre pyrolysis gasoline (WTPG) (plastic pyrolysis oil) using organic solvents such as diethylene glycol (DEG) (page 113, Abstract; page 120, Conclusion).
It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to have modified the Zhang process to add pour point depressant to pyrolysis oil to upgrade the pyrolysis oil as taught by Chen and to provide the extraction solvent comprise diethylene glycol as taught by Usman to arrive at the applicants’ claimed process.
Claim(s) 22 is/are rejected under 35 U.S.C. 103 as being unpatentable over Zhang et al (WO 2020/178599 A1), as applied to claim 1 above, and further in view of Van Der Reed et al (US 2018/0010050 A1).
Zhang discloses a process of upgrading a pyrolysis oil derived from the pyrolysis of plastic comprising adding a polar organic upgrading solvent immiscible in the pyrolysis oil to produce an extract phase and a raffinate phase. These immiscible phases are separated to yield an upgraded pyrolysis oil product (the abstract, 0058, 0075, 0079, 0096).
Zhang does not disclose adding an antioxidant or pour point depressant to the pyrolysis oil. However, Van Der Ree discloses adding a radical inhibitor to product of pyrolysis of plastic (paragraphs 0078; 0119) to prevent formation of long chain paraffins as reflux via stream 17 (0116 to 0119; see the figure). Note that the hydrocarbons in the column 13, 14, 15, and 16 are pyrolysis oils. The stream “Oil Product” from the column is the pyrolysis oil.
It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to have modified the Zhang process to add antioxidants to the pyrolysis oil to prevent the formation of long chain paraffins as taught by Van Der Ree to arrive at the applicants’ claimed process.
Claim(s) 24 and 27 is/are rejected under 35 U.S.C. 103 as being unpatentable over Zhang et al (WO 2020/178599 A1) in view of Chen et al. (Bioaugmentation for treatment of full-scale diethylene glycol monobutyl ether (DGBE) wastewater by Serratia sp. BDG-2, Journal of Hazardous Materials 309 (2016) 20–26, hereinafter “Chen_2016”) and ESATMAN (EASTMAN Products- EB solvent (ethylene glycol monobutyl ether).
Zhang discloses a process a discussed above.
But Zhang does not disclose the extraction solvent comprise diethylene glycol monobutyl ether, or ethylene glycol monobutyl ether.
However, Chen_2016 discloses diethylene glycol monobutyl ether (DGBE) is widely used as a solvent for industrial production of chemicals (page 20, 1. Introduction) and ESATMAN discloses ethylene glycol monobutyl ether is widely used as a solvent for industrial production of chemicals (pages 1-3).
It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to have modified the Zhang process to provide the extraction solvent comprise diethylene glycol monobutyl ether as taught by Chen_2016, or ethylene glycol monobutyl ether as taught by ESATMAN to arrive at the applicants’ claimed process.
Claim(s) 28-30 is/are rejected under 35 U.S.C. 103 as being unpatentable over Zhang et al (WO 2020/178599 A1, hereinafter “Zhang”).
In regard to claims 28 and 29, Zhang discloses a process of upgrading a pyrolysis oil derived from the pyrolysis of plastic comprising adding a polar organic upgrading solvent immiscible in the pyrolysis oil to produce an extract phase and a raffinate phase. These immiscible phases are separated to yield an upgraded pyrolysis oil product (the abstract, paragraphs 0058, 0075, 0079, 0096).
Zhang discloses the polar organic upgrading solvent (i.e., an extraction solvent) comprises acetone (paragraph 00140), and/or diethylenetriamine (paragraph 00146).
But Zhang does not disclose the extract phase comprises a foulant comprising a polyamide, and the polyamide comprises a hydroxyl group.
However, Zhang discloses the pyrolysis oil is derived from a thermoplastic polymers comprising polyamides and polyamideimide (paragraph [0051]).
Since the pyrolysis oil is derived from polymers comprising polyamides and polyamideimide, one skilled in the art would have reasonably expected that the extract phase and/or raffinate phase comprises a certain amount of polyamide, thereby renders the recitation “the extract phase comprises a foulant comprising a polyamide” recited in claim 28.
In addition, it is known in the art that polyamide comprises hydroxyl function group depending on the monomer material that comprises carboxylic acid functional group (-COOH) as evidenced by Tanaka et al. (Synthesis of Polyamides by Direct Polycondensation with Picryl Chloride. II. Reaction Conditions and Mechanism, Polymer Journal, Vol. 14, No. 8, pp 635-642 (1982), see page 636, Table 1), or Ogata et al. (The Reaction Mechanism of Polyamide Synthesis by Phosphorylation, Polymer Journal, Vol. 6, No. 6, pp 461-472 (1974)).
The recitation “the extract phase comprises a foulant comprising a polyamide, and the polyamide comprises a hydroxyl group” is considered prima facie obvious over Zhang, and as evidenced by Tanaka et al. and/or Ogata et al.
The composition of polyamide recited in claim 29 is also considered obvious by selecting appropriate polyamides with appropriate monomer and reaction mechanisms over Zhang, and as evidenced by Tanaka et al. and/or Ogata et al.
Regarding claim 30, Zhang discloses the pyrolysis oil contains unwanted substances which are removed during upgrading step. One of them is olefins (paragraphs 0061, 0062, 0081, 0111).
Claim(s) 31 is/are rejected under 35 U.S.C. 103 as being unpatentable over Zhang et al (WO 2020/178599 A1), as applied to claim 28 above, and further in view of Van Der Reed et al (US 2018/0010050 A1).
Zhang discloses a process of upgrading a pyrolysis oil derived from the pyrolysis of plastic comprising adding a polar organic upgrading solvent immiscible in the pyrolysis oil to produce an extract phase and a raffinate phase. These immiscible phases are separated to yield an upgraded pyrolysis oil product (the abstract, 0058, 0075, 0079, 0096).
Zhang does not disclose adding an antioxidant or pour point depressant to the pyrolysis oil. However, Van Der Ree discloses adding a radical inhibitor to product of pyrolysis of plastic (paragraphs 0078; 0119) to prevent formation of long chain paraffins as reflux via stream 17 (0116 to 0119; see the figure). Note that the hydrocarbons in the column 13, 14, 15, and 16 are pyrolysis oils. The stream “Oil Product” from the column is the pyrolysis oil.
It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to have modified the Zhang process to add antioxidants to the pyrolysis oil to prevent the formation of long chain paraffins as taught by Van Der Ree to arrive at the applicants’ claimed process.
Conclusion
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/YOUNGSUL JEONG/Primary Examiner, Art Unit 1772
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