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 .
Claim Rejections - 35 USC § 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(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.
Claims 1, 5, 8, 10, 12, 13, 16-18, 20, and 21 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Jia et al. (Catal. Sci. Technol., 2018, 8, 4665–4677).
Considering Claim 1: Jia et al. teaches a process for depolymerizing lignin comprising electro-oxidizing lignin on an anode, followed by electro-reducing the lignin on a cathode to form depolymerized lignin having a reduced molecular weight (Abstract, Section 2.4, Table 4), where the reduction takes place in a 1.0 NaOH solution/at a pH greater than 9 in the absence of thio compound (Section 2.4).
Considering Claim 5: Jia et al. teaches the lignin as comprising ether linages that are cleaved by the electrolysis (Section 3.3).
Considering Claim 8 and 10: Jia et al. teaches the lignin material as having a starting molecular weight of greater than 10,000 (Table 4).
Considering Claims 12 and 13: Jia et al. teaches the reaction products as comprising aromatic monomers substituted with hydroxyl, groups, ether groups, carboxyl groups, and ketone groups, with vanillin, guaiacol, and syringol being named products (Table 2 and 3).
Considering Claims 16 and 17: Jia et al. teaches an electrolyte solution comprising sodium hydroxide/a base and electrolyte, in water (Section 2.4).
Considering Claim 18: Jia et al. teaches the lignin is present in an amount of 20 to 60 g/L (Fig. 11).
Considering Claim 20: Jia et al. teaches an undivided cell (Section 2.4).
Considering Claim 21: Jia et al. teaches the reaction as occurring at 10-60 mA/cm2, at 25-65 ºC, for 1-5 hours (Section 2.4).
Claims 3 is rejected under 35 U.S.C. 102(a)(1) as being anticipated by Jia et al. (Catal. Sci. Technol., 2018, 8, 4665–4677).
Considering Claim 3: Jia et al. teaches a process for depolymerizing lignin comprising electro-oxidizing lignin on an anode, followed by electro-reducing the lignin on a cathode to form depolymerized lignin having a reduced molecular weight (Abstract, Section 2.4, Table 4), where the reduction takes place in a 1.0 NaOH solution/at a pH greater than 9 in the absence of thio compound (Section 2.4).
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.
Claim 15 is rejected under 35 U.S.C. 103 as being unpatentable over Jia et al. (Catal. Sci. Technol., 2018, 8, 4665–4677) as applied to claim 1 above.
Considering Claim 15: Jia et al. teaches the process of claim 1 as shown above.
Jia et al. does not teach the amount of ethyl acetate soluble and water soluble fractions. However, Jia et al. does teaches optimizing the process to reduce the amount insoluble lignin (Section 3.4). It would have been obvious to a person of ordinary skill in the art to have optimized the amount of insoluble product through routine experimentation, and the motivation to do so would have been, as Jia et al. suggests, to provide a high yield of monomer and oligomeric products for further use.
Claim 23 is rejected under 35 U.S.C. 103 as being unpatentable over Jia et al. (Catal. Sci. Technol., 2018, 8, 4665–4677).
Considering Claim 1: Jia et al. teaches a process for depolymerizing lignin comprising electro-oxidizing lignin on an anode, followed by electro-reducing the lignin on a cathode to form depolymerized lignin having a reduced molecular weight (Abstract, Section 2.4, Table 4), where the oxidation takes place in a 1.0 NaOH solution/at a pH greater than 9 in the absence of thio compound (Section 2.4).
. Jia et al. does not teach the amount of ethyl acetate soluble and water soluble fractions. However, Jia et al. does teaches optimizing the process to reduce the amount insoluble lignin (Section 3.4). It would have been obvious to a person of ordinary skill in the art to have optimized the amount of insoluble product through routine experimentation, and the motivation to do so would have been, as Jia et al. suggests, to provide a high yield of monomer and oligomeric products for further use.
Claims 1, 2, 4-9, 12-19, and 21 are rejected under 35 U.S.C. 103 as being unpatentable over Fang et al. (Green Chem. 2021, 23, 412, available 12/8/20) in view of over Jia et al. (Catal. Sci. Technol., 2018, 8, 4665–4677).
Considering Claim 1: Fang et al. teaches a process for depolymerizing lignin comprising oxidizing a lignin to form an oxidized lignin compound (pg. 420); and electrochemically reducing the oxidized lignin compound (pg. 420) to cleave the lignin polymer, i.e. reduce the molecular weight (pg. 413). Fang et al. teaches example without added thiol compounds (pg. 420).
Fang et al. teaches the pH of the reduction step as being 8. However, Jia et al. teaches a lignin electroreduction process, where the reduction takes place in a 1.0 NaOH solution/at a pH greater than 9 in the absence of thio compound (Section 2.4). Fang et al. and Jia et al. are analogous art as they are concerned with the same field of endeavor, namely lignin electroreduction. It would have been obvious to a person of ordinary skill in the art to have used the pH of Jia et al. in the electroreduction step of Fang et al., and the motivation to do so would have been, as Jia et al. suggests, to increase the solublity of the lignin in the electrolyte solution (Section 2.3).
Considering Claim 2: Fang et al. teaches the lignin as being chemically oxidized (pg. 420).
Considering Claim 4: Fang et al. teaches the lignin as being isolated via copper catalyzed alkaline hydrogen peroxide pretreatment (pg. 420).
Considering Claim 5: Fang et al. teaches the lignin as having β-O-4 linkages (pg. 413).
Considering Claims 6 and 7: The Office realizes that all of the claimed effects or physical properties are not positively stated by the reference(s). However, the reference(s) teaches all of the claimed ingredients, in the claimed amounts, and teaches the composition as being made by a substantially similar process. The original specification does not provide any disclosure on how to obtain the claimed properties outside the components of the composition itself. Therefore, the claimed effects and physical properties, i.e. the reduction in linkages and molecular weight, would necessarily arise from a composition with all the claimed ingredients in the claimed amounts. "Products of identical chemical composition can not have mutually exclusive properties." In re Spada, 911 F.2d 705, 709, 15 USPQ2d 1655, 1658 (Fed. Cir. 1990). A chemical composition and its properties are inseparable. Therefore, if the prior art teaches the identical chemical structure, the properties applicant discloses and/or claims are necessarily present. If it is the applicant’s position that this would not be the case: (1) evidence would need to be provided to support the applicant’s position; and (2) it would be the Office’s position that the application contains inadequate disclosure that there is no teaching enabling a person of ordinary skill in the art to obtain the claimed properties with only the claimed ingredients, absent undue experimentation.
Considering Claim 8: Fang et al. teaches the product following depolymerization as having a molecular weight of 600-1000 Da (pg. 418), and thus the starting material must have a molecular weight above 400 Da.
Considering Claim 9: The Office realizes that all of the claimed effects or physical properties are not positively stated by the reference(s). However, the reference(s) teaches all of the claimed ingredients, in the claimed amounts, and teaches the composition as being made by a substantially similar process. The original specification does not provide any disclosure on how to obtain the claimed properties outside the components of the composition itself. Therefore, the claimed effects and physical properties, i.e. the reduction in linkages and molecular weight, would necessarily arise from a composition with all the claimed ingredients in the claimed amounts. "Products of identical chemical composition can not have mutually exclusive properties." In re Spada, 911 F.2d 705, 709, 15 USPQ2d 1655, 1658 (Fed. Cir. 1990). A chemical composition and its properties are inseparable. Therefore, if the prior art teaches the identical chemical structure, the properties applicant discloses and/or claims are necessarily present. If it is the applicant’s position that this would not be the case: (1) evidence would need to be provided to support the applicant’s position; and (2) it would be the Office’s position that the application contains inadequate disclosure that there is no teaching enabling a person of ordinary skill in the art to obtain the claimed properties with only the claimed ingredients, absent undue experimentation.
Considering Claims 12 and 13: Fang et al. teaches the lignin product as comprising monomers such as syringic acid, vanillin, and phenol (Fig. 7).
Considering Claim 14: Fang et al. teaches the lignin product as being 24% ethyl acetate soluble (Fig. 6) and the ethyl acetate soluble fraction as being 27% monomer (S22). Thus the amount of monomer is about 6% of the original lignin.
Considering Claim 15: Fang et al. teaches the amount of ethyl acetate soluble product as being 24 weight percent and the amount of water soluble fraction as being 22 weight percent of the degradation product (Fig. 6).
Considering Claim 16: Fang et al. teaches reducing the oxidized lignin in an aqueous electrolyte medium (pg. 417).
Considering Claim 17: Fang et al. teaches the electrolyte medium as comprising a phosphate buffer (which comprises water), isopropanol and a LiBF4 electrolyte (pg. 420).
Considering Claim 18: Fang et al. teaches lignin as being present in an amount of 100 mg/40 mL of solvent (pg. 420) or 2.5 g/L.
Considering Claim 19: Fang et al. teaches reducing the lignin in the cathode compartment of a divided cell (Fig. 1).
Considering Claim 21: Fang et al. teaches the reduction as occurring at room temperature at 2.5 mA/cm2 for 1.5 hours (Abstract).
Claims 10 and 11 are rejected under 35 U.S.C. 103 as being unpatentable over Fang et al. (Green Chem. 2021, 23, 412, available 12/8/20) in view of over Jia et al. (Catal. Sci. Technol., 2018, 8, 4665–4677), as applied to claim 1 above, and further in the view of the evidence of Bhalla et al. (Biotechnol Biofuels (2016) 9:34).
Considering Claim 10: Fang et al. teaches the process of claim 1 as shown above. Fang et al. teaches the lignin as being produced by the process of Bhalla et al. (pg. 420). Bhalla et al. teaches the lignin as having a weight average molecular weight of 22,000 (Abstract).
Considering Claim 11: The Office realizes that all of the claimed effects or physical properties are not positively stated by the reference(s). However, the reference(s) teaches all of the claimed ingredients, in the claimed amounts, and teaches the composition as being made by a substantially similar process. The original specification does not provide any disclosure on how to obtain the claimed properties outside the components of the composition itself. Therefore, the claimed effects and physical properties, i.e. the reduction in linkages and molecular weight, would necessarily arise from a composition with all the claimed ingredients in the claimed amounts. "Products of identical chemical composition can not have mutually exclusive properties." In re Spada, 911 F.2d 705, 709, 15 USPQ2d 1655, 1658 (Fed. Cir. 1990). A chemical composition and its properties are inseparable. Therefore, if the prior art teaches the identical chemical structure, the properties applicant discloses and/or claims are necessarily present. If it is the applicant’s position that this would not be the case: (1) evidence would need to be provided to support the applicant’s position; and (2) it would be the Office’s position that the application contains inadequate disclosure that there is no teaching enabling a person of ordinary skill in the art to obtain the claimed properties with only the claimed ingredients, absent undue experimentation.
Claim 20 is rejected under 35 U.S.C. 103 as being unpatentable over Fang et al. (Green Chem. 2021, 23, 412, available 12/8/20) in view of over Jia et al. (Catal. Sci. Technol., 2018, 8, 4665–4677) as applied to claim 1 above, and further in view of Yang et al. (J. Org. Chem. 2021, 86, 15927−15934, available 6/10/21).
Considering Claim 20: Fang et al. teaches the process of claim 1 as shown above.
Fang et al. does not teach the reduction as occurring in an undivided electrochemical cell. However, Yang et al. teaches reducing lignin model compounds in an undivided electrochemical cell (pg. 15931). Fang et al. and Yang et al. are analogous art as they are concerned with the same field of endeavor, namely lignin depolymerization. It would have been obvious to a person of ordinary skill in the art to have used the undivided electrochemical cell of Yang et al. in the place of the divided cell of Fang et al., and the motivation to do so would have been, as Yang et al. suggests, the use of the undivided cell simplifies the reaction setup with minimal yield decrease (pg. 15931).
Claim 3 is rejected under 35 U.S.C. 103 as being unpatentable over Fang et al. (Green Chem. 2021, 23, 412, available 12/8/20) in view of Du et al. (ChemSusChem 2020, 13, 4318-4343).
Considering Claim 3: Fang et al. teaches a process for depolymerizing lignin comprising oxidizing a lignin to form an oxidized lignin compound (pg. 420); and electrochemically reducing the oxidized lignin compound (pg. 420) to cleave the lignin polymer, i.e. reduce the molecular weight (pg. 413). Fang et al. teaches example without added thiol compounds (pg. 420).
Fang et al. does not teach the oxidation as being anodic oxidation. However, Du et al. teaches using an anodic oxidation to oxidize lignin for depolymerization (pg. 4319). Fang et al. and Du et al. are analogous art as they are concerned with the same field of endeavor, namely lignin depolymerization. It would have been obvious to a person of ordinary skill in the art to have oxidized the lignin of Fang et al. with the anodic oxidation of Du et al., and the motivation to do so would have been, as Du et al. suggests, electrochemical depolymerization is low cost, reagent free, environmentally friendly and is carried out at milder conditions (pg. 4319).
Response to Arguments
Applicant's arguments filed April 30, 2026 have been fully considered but they are not persuasive, because:
The applicant’s argument that a person of ordinary skill in the art would not be motivated to modify the control example of Fang et al. without also adding the thio compound is not persuasive. Fang et al. teaches a process for depolymerizing lignin without the thio compound that results in depolymerization of lignin and the production of the target compounds. While the thio-assisted process has increased yield (pg. 417-418), the process without the thio compound is also functional. Disclosed examples and preferred embodiments do not constitute a teaching away from a broader disclosure or nonpreferred embodiments. In re Susi, 440 F.2d 442, 169 USPQ 423 (CCPA 1971). "A known or obvious composition does not become patentable simply because it has been described as somewhat inferior to some other product for the same use." In re Gurley, 27 F.3d 551, 554, 31 USPQ2d 1130, 1132 (Fed. Cir. 1994) (The invention was directed to an epoxy impregnated fiber-reinforced printed circuit material. The applied prior art reference taught a printed circuit material similar to that of the claims but impregnated with polyester-imide resin instead of epoxy. The reference, however, disclosed that epoxy was known for this use, but that epoxy impregnated circuit boards have "relatively acceptable dimensional stability" and "some degree of flexibility," but are inferior to circuit boards impregnated with polyester-imide resins. The court upheld the rejection concluding that applicant’s argument that the reference teaches away from using epoxy was insufficient to overcome the rejection since "Gurley asserted no discovery beyond what was known in the art." Id. at 554, 31 USPQ2d at 1132.).
It would have been obvious to a person of ordinary skill in the art to have started from the process without the thio compounds for the modification, as it is a known and functional process for depolymerizing lignin.
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.
Correspondence
Any inquiry concerning this communication or earlier communications from the examiner should be directed to LIAM J HEINCER whose telephone number is (571)270-3297. The examiner can normally be reached M-F 7:30-5:00.
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/LIAM J HEINCER/Primary Examiner, Art Unit 1767
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