Prosecution Insights
Last updated: October 25, 2026
Application No. 18/483,617

CHELATOR-MEDIATED FENTON (CMF) PROCESSES TO MODIFY LIGNIN

Non-Final OA §103§112
Filed
Oct 10, 2023
Priority
Apr 11, 2021 — provisional 63/173,478 +1 more
Examiner
KARST, DAVID THOMAS
Art Unit
1767
Tech Center
1700 — Chemical & Materials Engineering
Assignee
National Technology & Engineering Solutions of Sandia LLC
OA Round
1 (Non-Final)
65%
Grant Probability
Moderate
1-2
OA Rounds
0m
Est. Remaining
74%
With Interview

Examiner Intelligence

Grants 65% of resolved cases
65%
Career Allowance Rate
656 granted / 1013 resolved
At TC average
Moderate +10% lift
Without
With
+9.7%
Interview Lift
resolved cases with interview
Typical timeline
2y 11m
Avg Prosecution
51 currently pending
Career history
1074
Total Applications
across all art units

Statute-Specific Performance

§101
1.3%
-38.7% vs TC avg
§103
49.2%
+9.2% vs TC avg
§102
13.4%
-26.6% vs TC avg
§112
27.5%
-12.5% vs TC avg
Black line = Tech Center average estimate • Based on career data from 1013 resolved cases

Office Action

§103 §112
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 . Election/Restrictions Applicant's election with traverse of Group I, claims 1-15, in the reply filed on 08/03/2026 is acknowledged. Applicant's election with traverse of Group I, claims 1-15, in the reply filed on 08/03/2026 is acknowledged. Since amended claims 16-19 are drawn to the method of claim 1, they are placed in Group I. The traversal is on the ground(s) that claim 20 is amended to depend from Claim 1, and that accordingly, all the claims of Group IV contain all the claim elements of Claim 1 of Group I. This is not found persuasive because the invention of Group I and the invention of Group IV are independent or distinct, each from the other because inventions I and IV are related as process of making and product made. The inventions are distinct if either or both of the following can be shown: (1) that the process as claimed can be used to make another and materially different product or (2) that the product as claimed can be made by another and materially different process (MPEP § 806.05(f)). In the instant case the process as claimed can be used to make another and materially different product because the method of claim 1 will not necessarily make a mixture of modified lignin having (b) increased average MW of lignosulfate or lignin, wherein the (b) increased average MW of lignosulfate or lignin, is produced from the method of claim 1. The traversal is also on the ground that there is no substantial additional burden to search for prior art for Group IV over a prior art search for Group I. This is not found persuasive because there would be a serious search and/or examination burden if restriction were not required because it is necessary to search for one of the inventions in a manner that is not likely to result in finding art pertinent to the other invention, such as employing different search queries because the inventions are independent and distinct from each other as explained above. The traversal is also on the ground that all the Groups I and IV are classified in C07G1/00. This is not found persuasive because restriction practice under 35 U.S.C. 121 does not require the groups of inventions to be classified in different classes. The requirement is still deemed proper and is therefore made FINAL. Claim 20 is withdrawn from further consideration pursuant to 37 CFR 1.142(b), as being drawn to a nonelected invention, there being no allowable generic or linking claim. Applicant timely traversed the restriction (election) requirement in the reply filed on 08/03/2026. Priority Applicant’s claim for the benefit of a prior-filed application under 35 U.S.C. 119(e) or under 35 U.S.C. 120, 121, 365(c), or 386(c) is acknowledged. 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. The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph: The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention. Claims 1-19 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention. Claim 1 recites the limitation “(e) introducing further oxidizing agent to the reaction mixture incubating step (c)” in lines 5-6, which is indefinite because it is unclear what is referenced by “the reaction mixture incubating step (c)”. For further examination of the claims, this limitation is interpreted as “(e) introducing further oxidizing agent to the reaction mixture during step (c)”. Claim 3 recites the limitation “the method further comprises: the contacting a Fe salt and a chelator step occurs prior to concurrently with contact step (a)” in lines 1-2, which is indefinite because it is unclear how “occurs prior to concurrently with contact step (a)” limits “the contacting a Fe salt and a chelator step” because “prior to” “contact step (a)” means occurring earlier than “contact step (a)”, and “concurrently” “with contact step (a)” means occurring at the same time as “contact step (a)”. For further examination of the claims, this limitation is interpreted as “wherein the contacting a Fe salt and a chelator step occurs prior to or concurrently with contact step (a)”. Claim 18 recites the limitation “the lignosulfonate and/or lignin” in line 7. There is insufficient antecedent basis for this limitation in the claim because claim 1 does not recite the limitation “a lignosulfonate”. Since claim 1 recites the limitation “lignin” in lines 1, 3, 8, and 10, for further examination of the claims, this limitation is interpreted as “the lignin”. Claim Rejections - 35 USC § 103 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. Claims 1-15, 18, and 19 are rejected under 35 U.S.C. 103 as being unpatentable over Kent (US 2019/0002490 A1, cited in IDS). Regarding claim 1, Kent teaches steps involved in a method to convert water-insoluble lignin into a water-soluble material, wherein the steps are [0033] preparing an equimolar stock solution of dihydroxybenzene (DHB) and FeCl3 in water at pH 6, allowing the solution to incubate at least 30 min to allow DHB/Fe(III) complexes to form, using that stock solution to prepare a solution of 4 mM DHB/Fe(III) in water at pH 6 containing lignin at 400 mg/8 ml, stirring the mixture vigorously for 24 h, then adding sufficient hydrogen peroxide (H2O2) to make 0.5%(40 mg/8 ml), and allowing the reaction to proceed for 48 h, resulting in solubilization of 20 mg of the water-insoluble lignin into an aqueous solution at pH 6 [0034], wherein the method uses Fenton chemistry (FeCl2+ H2O2) and chelator-mediated Fenton chemistry (FeCl3+DHB+ H2O2) at the appropriate level of severity to generate hydroxyl radical that preferentially adds to aromatic rings and, under appropriate conditions, leads to opening of aromatic rings to yield polyacids [0036], wherein if the lignin is present in large excess, all the Fe will be associated with lignin and therefore the reaction with H2O2 will only occur in close proximity to lignin [0045], wherein this results in highly efficient use of the H2O2 for oxidizing the lignin chains [0045], wherein since the reaction occurs mainly near the lignin polymer, further oxidation of solubilized fragments that are released into solution will be minimized, avoiding generation of low MW acids and also loss of carbon as CO2 [0045], which reads on a method to convert water-insoluble lignin into water-soluble polyacid, the method comprising: (a) contacting a chelator/Fe complex with a water-insoluble lignin to produce a reaction mixture, (b) introducing an oxidizing agent to the reaction mixture, and (c) incubating the reaction mixture for a suitable period of time, such that greater than 0% of the water-insoluble lignin in the reaction mixture is converted into a water-soluble polyacid by the opening of at least one aromatic ring in each water-insoluble lignin. Kent does not teach that the method further comprises (d) introducing further water-insoluble lignin to the reaction mixture during step (c), (e) introducing further oxidizing agent to the reaction mixture incubating step (c), and (f) optionally repeating step (d) and/or step (e) one or more times, such that at least about 90% of the water-soluble lignin in the reaction mixture is converted into a water-soluble polyacid by the opening of at least one aromatic ring in each water-insoluble lignin. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to add Kent’s lignin in excess to the product of Kent’s allowing the reaction to proceed for 48 h, to then add a sufficient amount of Kent’s hydrogen peroxide (H2O2), and to optimize the amount of Kent’s lignin that has aromatic rings that are opened in Kent’s method to yield polyacids to be at least about 90%. The proposed modification would read on the method further comprising (d) introducing further water-insoluble lignin to the reaction mixture during step (c), and (e) introducing further oxidizing agent to the reaction mixture incubating step (c), such that at least about 90% of the water-soluble lignin in the reaction mixture is converted into a water-soluble polyacid by the opening of at least one aromatic ring in each water-insoluble lignin as claimed. The proposed modification would satisfy the method further comprising (f) optionally repeating step (d) and/or step (e) one or more times as claimed since it is optional. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for promoting all Kent’s Fe being associated with Kent’s lignin, for promoting the reaction with Kent’s H2O2 only occurring in close proximity to Kent’s lignin, for promoting highly efficient use of Kent’s H2O2 for oxidizing Kent’s lignin chains, for preventing oxidation of solubilized fragments that are released into solution in Kent’s method, for preventing generation of low MW acids and loss of carbon as CO2 in Kent’s method, and for optimizing an amount of polyacids that are yielded from Kent’s lignin in Kent’s method because Kent teaches that the steps involved in a method to convert water-insoluble lignin into a water-soluble material comprise [0033] using that stock solution to prepare a solution of 4 mM DHB/Fe(III) in water at pH 6 containing lignin at 400 mg/8 ml, stirring the mixture vigorously for 24 h, then adding sufficient hydrogen peroxide (H2O2) to make 0.5%(40 mg/8 ml), and allowing the reaction to proceed for 48 h, resulting in solubilization of 20 mg of the water-insoluble lignin into an aqueous solution at pH 6 [0034], that the method uses Fenton chemistry (FeCl2+ H2O2) and chelator-mediated Fenton chemistry (FeCl3+DHB+ H2O2) at the appropriate level of severity to generate hydroxyl radical that preferentially adds to aromatic rings and, under appropriate conditions, leads to opening of aromatic rings to yield polyacids [0036], that if the lignin is present in large excess, all the Fe will be associated with lignin and therefore the reaction with H2O2 will only occur in close proximity to lignin [0045], that this results in highly efficient use of the H2O2 for oxidizing the lignin chains [00415], and that since the reaction occurs mainly near the lignin polymer, further oxidation of solubilized fragments that are released into solution will be minimized, avoiding generation of low MW acids and also loss of carbon as CO2 [0045], which means that the amount of Kent’s lignin that has aromatic rings that are opened in Kent’s method to yield polyacids in % would have affected an amount of polyacids that are yielded from Kent’s lignin in Kent’s method. Regarding claims 2-8, Kent teaches that the steps are [0033] preparing an equimolar stock solution of dihydroxybenzene (DHB) and FeCl3 in water at pH 6, allowing the solution to incubate at least 30 min to allow DHB/Fe(III) complexes to form, and using that stock solution to prepare a solution of 4 mM DHB/Fe(III) in water at pH 6 containing lignin at 400 mg/8 ml [0034], which reads on the method further comprises: contacting a Fe salt and a chelator to form the chelator/Fe complex as claimed, the method further comprises: the contacting a Fe salt and a chelator step occurs prior to concurrently with contacting step (a) as claimed, wherein the Fe salt is any Fe(III) salt as claimed, wherein the Fe salt is FeX3, wherein X is any halide as claimed, wherein X is Cl as claimed, wherein the chelator is any chelator that can chelate Fe to facilitate the reduction of Fe(III) to Fe(II) as claimed, wherein the chelator is 1,2-dihydroxybenzene (DHB) as claimed. Regarding claim 9, Kent does not teach that the method further comprises a concentration step and/or separating step, and Kent’s method would not inherently further comprise a concentration step and/or separating step, which reads on wherein the method lacks a concentration step and/or separating step as claimed. Regarding claim 10, Kent teaches that the steps involved in a method to convert water-insoluble lignin into a water-soluble material are [0033] preparing an equimolar stock solution of dihydroxybenzene (DHB) and FeCl3 in water at pH 6, allowing the solution to incubate at least 30 min to allow DHB/Fe(III) complexes to form, using that stock solution to prepare a solution of 4 mM DHB/Fe(III) in water at pH 6 containing lignin at 400 mg/8 ml, stirring the mixture vigorously for 24 h, then adding sufficient hydrogen peroxide (H2O2) to make 0.5%(40 mg/8 ml), and allowing the reaction to proceed for 48 h, resulting in solubilization of 20 mg of the water-insoluble lignin into an aqueous solution at pH 6 [0034], wherein if the lignin is present in large excess, all the Fe will be associated with lignin and therefore the reaction with H2O2 will only occur in close proximity to lignin [0045], wherein this results in highly efficient use of the H2O2 for oxidizing the lignin chains [00415], wherein since the reaction occurs mainly near the lignin polymer, further oxidation of solubilized fragments that are released into solution will be minimized, avoiding generation of low MW acids and also loss of carbon as CO2 [0045], which reads on wherein the water-insoluble lignin is part of a solid component that is more than 0% by weight of the reaction mixture. Kent does not teach that the water-insoluble lignin is part of a solid component that is equal to or more than about 20% by weight of the reaction mixture. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to optimize the amount of Kent’s lignin in the product of Kent’s using that stock solution to prepare a solution of 4 mM DHB/Fe(III) in water at pH 6 containing lignin at 400 mg/8 ml to be equal to or more than about 20% by weight of Kent’s solution of DHB/Fe(III) in water containing lignin. The proposed modification would read on wherein the water-insoluble lignin is part of a solid component that is equal to or more than about 20% by weight of the reaction mixture as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for optimizing an amount of polyacids that are yielded from Kent’s lignin in Kent’s method because Kent teaches that the steps involved in a method to convert water-insoluble lignin into a water-soluble material comprise [0033] using that stock solution to prepare a solution of 4 mM DHB/Fe(III) in water at pH 6 containing lignin at 400 mg/8 ml [0034], that if the lignin is present in large excess, all the Fe will be associated with lignin and therefore the reaction with H2O2 will only occur in close proximity to lignin [0045], that this results in highly efficient use of the H2O2 for oxidizing the lignin chains [00415], and that since the reaction occurs mainly near the lignin polymer, further oxidation of solubilized fragments that are released into solution will be minimized, avoiding generation of low MW acids and also loss of carbon as CO2 [0045], which means that the amount of Kent’s lignin in the product of Kent’s using that stock solution to prepare a solution of 4 mM DHB/Fe(III) in water at pH 6 containing lignin at 400 mg/8 ml in % by weight of Kent’s solution of DHB/Fe(III) in water containing lignin would have affected an amount of polyacids that are yielded from Kent’s lignin in Kent’s method. Regarding claim 11, Kent teaches that steps involved in a method to convert water-insoluble lignin into a water-soluble material comprise [0033] using that stock solution to prepare a solution of 4 mM DHB/Fe(III) in water at pH 6 containing lignin at 400 mg/8 ml, stirring the mixture vigorously for 24 h, then adding sufficient hydrogen peroxide (H2O2) to make 0.5%(40 mg/8 ml), and allowing the reaction to proceed for 48 h, resulting in solubilization of 20 mg of the water-insoluble lignin into an aqueous solution at pH 6 [0034], that the method uses Fenton chemistry (FeCl2+ H2O2) and chelator-mediated Fenton chemistry (FeCl3+DHB+ H2O2) at the appropriate level of severity to generate hydroxyl radical that preferentially adds to aromatic rings and, under appropriate conditions, leads to opening of aromatic rings to yield polyacids [0036], that if the lignin is present in large excess, all the Fe will be associated with lignin and therefore the reaction with H2O2 will only occur in close proximity to lignin [0045], that this results in highly efficient use of the H2O2 for oxidizing the lignin chains [00415], and that since the reaction occurs mainly near the lignin polymer, further oxidation of solubilized fragments that are released into solution will be minimized, avoiding generation of low MW acids and also loss of carbon as CO2 [0045], which suggests continuously or semi-continuously adding Kent’s lignin in excess to the product of Kent’s allowing the reaction to proceed for 48 h, which suggests wherein the introducing step (d) is continuous or semi-continuous. Kent does not teach that the introducing step (d), introducing step (e), and/or repeating step (f) are continuous or semi-continuous. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to continuously or semi-continuously add Kent’s lignin in excess to the product of Kent’s allowing the reaction to proceed for 48 h, to then add a sufficient amount of Kent’s hydrogen peroxide (H2O2), and to optimize the amount of Kent’s lignin that has aromatic rings that are opened in Kent’s method to yield polyacids to be at least about 90%. The proposed modification would read on wherein the introducing step (d) is continuous or semi-continuous as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for promoting all Kent’s Fe being associated with Kent’s lignin, for promoting the reaction with Kent’s H2O2 only occurring in close proximity to Kent’s lignin, for promoting highly efficient use of Kent’s H2O2 for oxidizing Kent’s lignin chains, for preventing oxidation of solubilized fragments that are released into solution in Kent’s method, for preventing generation of low MW acids and loss of carbon as CO2 in Kent’s method, and for optimizing an amount of polyacids that are yielded from Kent’s lignin in Kent’s method because Kent teaches that the steps involved in a method to convert water-insoluble lignin into a water-soluble material comprise [0033] using that stock solution to prepare a solution of 4 mM DHB/Fe(III) in water at pH 6 containing lignin at 400 mg/8 ml, stirring the mixture vigorously for 24 h, then adding sufficient hydrogen peroxide (H2O2) to make 0.5%(40 mg/8 ml), and allowing the reaction to proceed for 48 h, resulting in solubilization of 20 mg of the water-insoluble lignin into an aqueous solution at pH 6 [0034], that the method uses Fenton chemistry (FeCl2+ H2O2) and chelator-mediated Fenton chemistry (FeCl3+DHB+ H2O2) at the appropriate level of severity to generate hydroxyl radical that preferentially adds to aromatic rings and, under appropriate conditions, leads to opening of aromatic rings to yield polyacids [0036], that if the lignin is present in large excess, all the Fe will be associated with lignin and therefore the reaction with H2O2 will only occur in close proximity to lignin [0045], that this results in highly efficient use of the H2O2 for oxidizing the lignin chains [00415], and that since the reaction occurs mainly near the lignin polymer, further oxidation of solubilized fragments that are released into solution will be minimized, avoiding generation of low MW acids and also loss of carbon as CO2 [0045], which means that the amount of Kent’s lignin that has aromatic rings that are opened in Kent’s method to yield polyacids in % would have affected an amount of polyacids that are yielded from Kent’s lignin in Kent’s method. Regarding claim 12, Kent teaches that steps involved in a method to convert water-insoluble lignin into a water-soluble material comprise [0033] preparing an equimolar stock solution of dihydroxybenzene (DHB) and FeCl3 in water at pH 6, allowing the solution to incubate at least 30 min to allow DHB/Fe(III) complexes to form, using that stock solution to prepare a solution of 4 mM DHB/Fe(III) in water at pH 6 containing lignin at 400 mg/8 ml, stirring the mixture vigorously for 24 h, then adding sufficient hydrogen peroxide (H2O2) to make 0.5%(40 mg/8 ml), and allowing the reaction to proceed for 48 h, resulting in solubilization of 20 mg of the water-insoluble lignin into an aqueous solution at pH 6 [0034], which reads on wherein the method further comprises (g) introducing a base to the reaction mixture to adjust the pH of the reaction mixture to about pH 6.0 as claimed. Kent satisfies (h) optionally repeating step (g) one or more times as claimed because it is optional. Regarding claim 13, Kent teaches steps involved in a method to convert water-insoluble lignin into a water-soluble material comprise [0033] preparing an equimolar stock solution of dihydroxybenzene (DHB) and FeCl3 in water at pH 6, allowing the solution to incubate at least 30 min to allow DHB/Fe(III) complexes to form, using that stock solution to prepare a solution of 4 mM DHB/Fe(III) in water at pH 6 containing lignin at 400 mg/8 ml, stirring the mixture vigorously for 24 h, then adding sufficient hydrogen peroxide (H2O2) to make 0.5%(40 mg/8 ml), and allowing the reaction to proceed for 48 h, resulting in solubilization of 20 mg of the water-insoluble lignin into an aqueous solution at pH 6 [0034], that reaction conditions must be controlled properly to obtain partially oxidized high MW ring-opened fragments [0036], that another aspect is to control the extent of ring opening, and therefore the relative amounts of hydrophobic and charged groups that strongly impact the effectiveness of a dispersant, through the reaction conditions [0036], and that a third aspect is to control the reaction conditions to maximize the production of solubilized lignin material per amount of H2O2 used [0036], which suggests modifying the temperature of Kent’s preparing an equimolar stock solution of dihydroxybenzene (DHB) and FeCl3 in water at pH 6, allowing the solution to incubate at least 30 min to allow DHB/Fe(III) complexes to form, using that stock solution to prepare a solution of 4 mM DHB/Fe(III) in water at pH 6 containing lignin at 400 mg/8 ml, stirring the mixture vigorously for 24 h, then adding sufficient hydrogen peroxide (H2O2) to make 0.5%(40 mg/8 ml), and allowing the reaction to proceed for 48 h, which suggests wherein the method further comprises: (i) heating the reaction mixture to a temperature. Kent does not teach that the method further comprises: (i) heating the reaction mixture to a temperature of about 40 °C to about 60 °C. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to optimize the temperature of Kent’s preparing an equimolar stock solution of dihydroxybenzene (DHB) and FeCl3 in water at pH 6, allowing the solution to incubate at least 30 min to allow DHB/Fe(III) complexes to form, using that stock solution to prepare a solution of 4 mM DHB/Fe(III) in water at pH 6 containing lignin at 400 mg/8 ml, stirring the mixture vigorously for 24 h, then adding sufficient hydrogen peroxide (H2O2) to make 0.5%(40 mg/8 ml), and/or allowing the reaction to proceed for 48 h to be about 40 °C to about 60 °C. The proposed modification would read on wherein the method further comprises: (i) heating the reaction mixture to a temperature of about 40 °C to about 60 °C as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for optimizing obtainment of partially oxidized high MW ring-opened fragments in Kent’s method, for optimizing extent of ring opening in Kent’s method, for optimizing effectiveness of a dispersant produced by Kent’s method, and for optimizing production of solubilized lignin material per amount of H2O2 used in Kent’s method because Kent teaches that steps involved in a method to convert water-insoluble lignin into a water-soluble material comprise [0033] preparing an equimolar stock solution of dihydroxybenzene (DHB) and FeCl3 in water at pH 6, allowing the solution to incubate at least 30 min to allow DHB/Fe(III) complexes to form, using that stock solution to prepare a solution of 4 mM DHB/Fe(III) in water at pH 6 containing lignin at 400 mg/8 ml, stirring the mixture vigorously for 24 h, then adding sufficient hydrogen peroxide (H2O2) to make 0.5%(40 mg/8 ml), and allowing the reaction to proceed for 48 h, resulting in solubilization of 20 mg of the water-insoluble lignin into an aqueous solution at pH 6 [0034], that reaction conditions must be controlled properly to obtain partially oxidized high MW ring-opened fragments [0036], that another aspect is to control the extent of ring opening, and therefore the relative amounts of hydrophobic and charged groups that strongly impact the effectiveness of a dispersant, through the reaction conditions [0036], and that a third aspect is to control the reaction conditions to maximize the production of solubilized lignin material per amount of H2O2 used [0036], which means that the temperature of Kent’s preparing an equimolar stock solution of dihydroxybenzene (DHB) and FeCl3 in water at pH 6, allowing the solution to incubate at least 30 min to allow DHB/Fe(III) complexes to form, using that stock solution to prepare a solution of 4 mM DHB/Fe(III) in water at pH 6 containing lignin at 400 mg/8 ml, stirring the mixture vigorously for 24 h, then adding sufficient hydrogen peroxide (H2O2) to make 0.5%(40 mg/8 ml), and/or allowing the reaction to proceed for 48 h in °C would have affected obtainment of partially oxidized high MW ring-opened fragments in Kent’s method, extent of ring opening in Kent’s method, effectiveness of a dispersant produced by Kent’s method, and production of solubilized lignin material per amount of H2O2 used in Kent’s method. Regarding claim 14, Kent teaches that steps involved in a method to convert water-insoluble lignin into a water-soluble material comprise [0033] then adding sufficient hydrogen peroxide (H2O2) to make 0.5%(40 mg/8 ml) [0036], that in some embodiments, the oxidizing agent is H2O2 or molecular oxygen (O2), or both [0010], and that in some embodiments, the introducing an oxidizing agent to the first solution step comprises bubbling a gas composition comprising O2 into the first solution [0011], which optionally reads on wherein the introducing step (b) and/or introducing step (e) comprises bubbling a gas composition comprising O2 into the reaction mixture as claimed. Kent does not teach as specific wherein the introducing step (b) and/or introducing step (e) comprises bubbling a gas composition comprising O2 into the reaction mixture. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to use bubbling a gas composition comprising O2 into Kent’s solution of 4 mM DHB/Fe(III) in water at pH 6 containing lignin at 400 mg/8 ml to substituted for Kent’s adding sufficient hydrogen peroxide (H2O2) to make 0.5%(40 mg/8 ml). The proposed modification would read on wherein the introducing step (b) and/or introducing step (e) comprises bubbling a gas composition comprising O2 into the reaction mixture as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying an extent of oxidation in Kent’s method because Kent teaches that steps involved in a method to convert water-insoluble lignin into a water-soluble material comprise [0033] then adding sufficient hydrogen peroxide (H2O2) to make 0.5%(40 mg/8 ml) [0036], that in some embodiments, the oxidizing agent is H2O2 or molecular oxygen (O2), or both [0010], and that in some embodiments, the introducing an oxidizing agent to the first solution step comprises bubbling a gas composition comprising O2 into the first solution [0011]. Regarding claim 15, Kent teaches that steps involved in a method to convert water-insoluble lignin into a water-soluble material comprise [0033] then adding sufficient hydrogen peroxide (H2O2) to make 0.5%(40 mg/8 ml) [0034], which reads on wherein the oxidizing agent is H2O2 as claimed. Regarding claim 18, Kent teaches that in some embodiments, water-soluble lignin polymer mixture produced by the method has an average molecular weight smaller than the average molecular weight of the lignin, or mixture of lignin, at the start of the method [007], that the results show that most of the water soluble material is composed of polymeric fragments with MW only slightly less than that of the original material [0035], that reaction conditions must be controlled properly to obtain partially oxidized high MW ring-opened fragments [0036], that since the reaction occurs mainly near the lignin polymer, further oxidation of solubilized fragments that are released into solution will be minimized, avoiding generation of low MW acids and also loss of carbon as CO2 [0045], and that the results demonstrate that the product of the reaction is a ring-opened polymer of a comparable molecular weight to the original material but including a small amount of low molecular weight species [0060], which suggests modifying Kent’s method such that the molecular weight of Kent’s water-soluble lignin that is a water-soluble polyacid that is produced by Kent’s method is higher than the molecular weight of Kent’s water-insoluble lignin that is used in Kent’s method, which suggests wherein the average molecules weight of the lignin in the reaction mixture is increased as claimed. Kent does not teach that the average molecular weight of the lignosulfonate and/or lignin in the reaction mixture is increased. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to modify Kent’s method such that the molecular weight of Kent’s water-soluble lignin that is a water-soluble polyacid that is produced by Kent’s method is higher than the molecular weight of Kent’s water-insoluble lignin that is used in Kent’s method. The proposed modification would read on wherein the average molecular weight of the lignosulfonate and/or lignin in the reaction mixture is increased as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying an amount of polyacids that are yielded from Kent’s lignin in Kent’s method because Kent teaches that steps involved in a method to convert water-insoluble lignin into a water-soluble material comprise [0033] using that stock solution to prepare a solution of 4 mM DHB/Fe(III) in water at pH 6 containing lignin at 400 mg/8 ml, stirring the mixture vigorously for 24 h, then adding sufficient hydrogen peroxide (H2O2) to make 0.5%(40 mg/8 ml), and allowing the reaction to proceed for 48 h, resulting in solubilization of 20 mg of the water-insoluble lignin into an aqueous solution at pH 6 [0034], that the method uses Fenton chemistry (FeCl2+ H2O2) and chelator-mediated Fenton chemistry (FeCl3+DHB+ H2O2) at the appropriate level of severity to generate hydroxyl radical that preferentially adds to aromatic rings and, under appropriate conditions, leads to opening of aromatic rings to yield polyacids [0036], that in some embodiments, water-soluble lignin polymer mixture produced by the method has an average molecular weight smaller than the average molecular weight of the lignin, or mixture of lignin, at the start of the method [007], that the results show that most of the water soluble material is composed of polymeric fragments with MW only slightly less than that of the original material [0035], that reaction conditions must be controlled properly to obtain partially oxidized high MW ring-opened fragments [0036], that since the reaction occurs mainly near the lignin polymer, further oxidation of solubilized fragments that are released into solution will be minimized, avoiding generation of low MW acids and also loss of carbon as CO2 [0045], and that the results demonstrate that the product of the reaction is a ring-opened polymer of a comparable molecular weight to the original material but including a small amount of low molecular weight species [0060]. Regarding claim 19, Kent teaches that steps involved in a method to convert water-insoluble lignin into a water-soluble material comprise [0033] using that stock solution to prepare a solution of 4 mM DHB/Fe(III) in water at pH 6 containing lignin at 400 mg/8 ml [0034], which reads on wherein the Fe concentration added to the reaction mixture has a concentration equal to or higher than about 10 mM, 15 mM, 20 mM, 25 mM, 30 mM, 35 mM, 40 mM, 45 mM, or 50 mM, or having a value within any two preceding values as claimed. Claims 16 and 17 are rejected under 35 U.S.C. 103 as being unpatentable over Kent (US 2019/0002490 A1, cited in IDS) as applied to claim 1, and further in view of Kijlstra et al. (WO 2020/025650 A1). Regarding claim 16, Kent renders obvious the method of claim 1 as explained above. Kent does not teach that the method of claim 1 further comprises (g) introducing a mixture of modified lignin comprising the water-soluble polyacid to soil, sand, or substrate for plants, or mixture thereof, to form an enhanced substrate composition. However, Kijlstra teaches controlled release formulations based on lignin, wherein the controlled release formulations can be applied to soil (p. 1, l. 3-7), that the controlled release formulations are for soil (p. 2, l. 7-8), that the controlled release formulations are applicable to soil (p. 3, l. 7), and that the lignin can be dissolved in a water soluble solvent, mixed with an aqueous dispersion, and applied to a soil substrate (p. 11, l. 19-22). Kent and Kijlstra are analogous art because both references are in the same field of endeavor of a method comprising use of lignin. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to apply Kent’s water-soluble material that is lignin that is water-soluble polyacid to soil, as suggested by Kijlstra. The proposed modification would read on the method of claim 1, the method further comprising (g) introducing a mixture of modified lignin comprising the water-soluble polyacid to soil, to form an enhanced substrate composition as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficia for providing an additional use for Kent’s water-soluble material that is lignin that is water-soluble polyacid because Kijlstra teaches controlled release formulations based on lignin, wherein the controlled release formulations can be applied to soil (p. 1, l. 3-7), that the controlled release formulations are for soil (p. 2, l. 7-8), that the controlled release formulations are applicable to soil (p. 3, l. 7), and that the lignin can be dissolved in a water soluble solvent, mixed with an aqueous dispersion, and applied to a soil substrate (p. 11, l. 19-22), and because Kent teaches that the method converts water-insoluble lignin into a water-soluble material [0033], and that the method leads to opening of aromatic rings to yield polyacids [0036]. Regarding claim 17, Kent in view of Kijlstra renders obvious the limitation method of claim 16, wherein the substrate for plants comprises used coffee grounds as claimed because claims 16 and 17 do not require the method to further comprise (g) introducing a mixture of modified lignin comprising the water-soluble polyacid to substrate for plants if the method further comprises (g) introducing a mixture of modified lignin comprising the water-soluble polyacid to soil, and Kent in view of Kijlstra renders it obvious that the method further comprises (g) introducing a mixture of modified lignin comprising the water-soluble polyacid to soil, as explained above for claim 16. Correspondence Any inquiry concerning this communication or earlier communications from the examiner should be directed to DAVID KARST whose telephone number is (571)270-7732. The examiner can normally be reached Monday-Friday 8:00 AM-5:00 PM. Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice. If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Mark Eashoo can be reached at 571-272-1197. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300. Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000. /DAVID T KARST/Primary Examiner, Art Unit 1767
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Prosecution Timeline

Oct 10, 2023
Application Filed
Oct 14, 2026
Non-Final Rejection mailed — §103, §112 (current)

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1-2
Expected OA Rounds
65%
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74%
With Interview (+9.7%)
2y 11m (~0m remaining)
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