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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 02/17/2026 has been entered.
In the amendments filed on 02/17/2026, claims 1-14, 16-19, and 21 are pending. Claims 1 and 2 are amended. Claims 15 and 20 are canceled. Claims 16-19 and 21 are withdrawn.
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.
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
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 1-11 are rejected under 35 U.S.C. 103 as being unpatentable over Barta et al. (WO 2014/201325 A2, cited in IDS, made of record on 05/31/2022) in view of Van Es et al. (WO 2014/168473 A1, cited in IDS, made of record on 08/05/2022).
Regarding claims 1 and 2, Barta teaches a method that includes the step of depolymerizing at least one biopolymer from the biopolymer source into an oligomer within a system comprised of at least one solvent and at least one catalyst (p. 6, l. 9-11), wherein the at least one biopolymer is lignin (p. 5, l. 13-14; p. 6, l. 14-15), wherein the solvent is optionally a mixture of water and at least one organic solvent (p. 20, l. 4-5), wherein non-limiting examples of organic solvents include methanol, ethanol, and isopropanol (p. 20, l. 1-2), wherein the system is optionally heated in a temperature range from 30 °C to 500 °C (p. 23, l. 27-28), wherein pressure is optionally applied to the system (p. 24, l. 6), wherein a gas is optionally added to the system to increase the pressure (p. 24, l. 8-9), wherein non-limiting examples of a gas include nitrogen, argon, and hydrogen (p. 24, l. 9-10), wherein the method optionally further includes the step of purifying the oligomer using a method of purification (p. 7, l. 6-7), wherein the method optionally further includes the step of purifying the monomer using a method of purification (p. 6, l. 4-6), wherein if necessary, the monomers can be further purified by any method known in the art, such as precipitation (p. 25, l. 8-10), which reads on a process for depolymerization of lignin comprising converting, optionally thermally, a mixture that is optionally an aqueous mixture and comprising lignin, catalyst, and optionally primary alcohol optionally in a non-oxidizing atmosphere optionally at a temperature of 30°C to 500°C, and which suggests thereby obtaining a precipitated lignin oligomer, and the process according to claim 1, comprising the steps of: a) providing a mixture that is optionally an aqueous mixture and comprising: lignin, catalyst, and optionally primary alcohol optionally in a non-oxidizing atmosphere, b) converting, optionally thermally, the lignin in the mixture that is optionally an aqueous mixture optionally at a temperature of 30°C to 500°C, and which suggests the process further comprising the step of c) obtaining precipitated lignin oligomer.
Barta does not teach a specific embodiment in which the converting is thermally converting and is at a temperature of at least 280°C, and in which the converting is thermally converting and is at a temperature of at least 280°C. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to use a step of heating Barta’s system to a temperature range that is optimized to be from 280 °C to 500 °C to modify Barta’s method. The proposed modification would read on the converting is thermally converting and is at a temperature of at least 280°C and at most 500°C as claimed, and the converting is thermally converting and is at a temperature of at least 280°C and at most 500°C 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 ability of Barta’s method to depolymerize lignin and for optimizing an extent of depolymerization of Barta’s lignin in Barta’s method because Barta teaches that the system is optionally heated in a temperature range from 30 °C to 500 °C (p. 23, l. 27-28), that the method includes the step of depolymerizing at least one biopolymer from the biopolymer source into an oligomer within a system comprised of at least one solvent and at least one catalyst (p. 6, l. 9-11), and that the at least one biopolymer is lignin (p. 5, l. 13-14; p. 6, l. 14-15), which means that the temperature range to which Barta’s system is heated in Barta’s method would have affected an extent of depolymerization of Barta’s lignin in Barta’s method.
Barta does not teach a specific embodiment in which the mixture is an aqueous mixture further comprising primary alcohol, and in which the mixture is an aqueous mixture further comprising primary alcohol. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to select Barta’s mixture of water and at least one organic solvent that is methanol, ethanol, or isopropanol as Barta’s at least one solvent in Barta’s method. The proposed modification would read on the mixture is an aqueous mixture further comprising primary alcohol as claimed, and the mixture is an aqueous mixture further comprising primary alcohol 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 solubility of Barta’s biopolymer in Barta’s solvent and/or for providing a species of solvent that is suitable for Barta’s method because Barta teaches that as would be understood by one skill in the art, any solvent in which the biopolymer is soluble is contemplated (p. 19, l. 32-33), that the system is optionally comprised of at least two solvents (p. 19, l. 31-32), that the solvent is optionally a mixture of water and at least one organic solvent (p. 20, l. 4-5), that non-limiting examples of organic solvents include methanol, ethanol, and isopropanol (p. 20, l. 1-2), that the method includes the step of depolymerizing at least one biopolymer from the biopolymer source into a monomer within a system comprised of at least one solvent and at least one catalyst (p. 5, l. 8-10) or includes the step of depolymerizing at least one biopolymer from the biopolymer source into an oligomer within a system comprised of at least one solvent and at least one catalyst (p. 6, l. 9-11), that the use of sequential extractions and/or fractionations permits the separation of biopolymers with different properties, such as average molecular weights, different chain lengths, polarity, or chemical functionality, based on the solubility of each biopolymer in the solvent(s) (p. 18, l. 26-29), and that the at least one biopolymer is lignin (p. 5, l. 13-14; p. 6, l. 14-15).
Barta does not teach a specific embodiment in which the converting is in a non-oxidizing atmosphere, and in which the providing the mixture is in a non-oxidizing atmosphere. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to use Barta’s step of applying pressure to Barta’s system by adding gas that is nitrogen, argon, or hydrogen to increase the pressure to modify Barta’s method. The proposed modification would read on the converting is in a non-oxidizing atmosphere as claimed, and the providing a mixture is in a non-oxidizing atmosphere as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for promoting depolymerization of lignin in Barta’s method because Barta teaches that pressure is optionally applied to the system (p. 24, l. 6), that a gas is optionally added to the system to increase the pressure (p. 24, l. 8-9), that the pressure can be any pressure that is sufficient to promote the depolymerization of a biopolymer (p. 24, l. 6-7), that non-limiting examples of a gas include nitrogen, argon, and hydrogen (p. 24, l. 9-10), that the method includes the step of depolymerizing at least one biopolymer from the biopolymer source into a monomer within a system comprised of at least one solvent and at least one catalyst (p. 5, l. 8-10) or includes the step of depolymerizing at least one biopolymer from the biopolymer source into an oligomer within a system comprised of at least one solvent and at least one catalyst (p. 6, l. 9-11), and that the at least one biopolymer is lignin (p. 5, l. 13-14; p. 6, l. 14-15).
Barta does not teach that the mixture has a pH of at least 9, and that the mixture has a pH of at least 9. However, Van Es teaches lignin depolymerization by placing mixed wheat straw and grass soda lignin and demineralized water in a reactor, adding catalyst, adjusting the pH of the resulting suspension to above pH 10 by adding aqueous sodium hydroxide, closing the reactor, stirring, heating the reactor to a desired temperature, after reaction, and rapidly cooling the reactor down to room temperature using a water bath (p. 11, l. 15-24). Barta and Van Es are analogous art because both references are in the same field of endeavor of a process for depolymerization of lignin. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to use a step of adjusting the pH of Barta’s system to above pH 10 by adding Van Es’s aqueous sodium hydroxide to Barta’s system to modify Barta’s method. The proposed modification would read on the mixture has a pH of greater than 10 as claimed, and the mixture has a pH of greater than 10 as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for completely dissolving Barta’s lignin in Barta’s system because Van Es teaches lignin depolymerization by placing mixed wheat straw and grass soda lignin and demineralized water in a reactor, adding catalyst, adjusting the pH of the resulting suspension to above pH 10 by adding aqueous sodium hydroxide, wherein above pH 10 the lignin was completely dissolved, closing the reactor, stirring, heating the reactor to a desired temperature, after reaction, and rapidly cooling the reactor down to room temperature using a water bath (p. 11, l. 15-24), and because completely dissolving Barta’s lignin in Barta’s system would have been desirable for Barta’s method because it would have improved uniformity of Barta’s depolymerization at least one biopolymer that is lignin because Barta teaches that the method includes the step of depolymerizing at least one biopolymer from the biopolymer source into a monomer within a system comprised of at least one solvent and at least one catalyst (p. 5, l. 8-10), or includes the step of depolymerizing at least one biopolymer from the biopolymer source into an oligomer within a system comprised of at least one solvent and at least one catalyst (p. 6, l. 9-11), that the at least one biopolymer is lignin (p. 5, l. 13-14; p. 6, l. 14-15), and that the solvent is optionally a mixture of water and at least one organic solvent (p. 20, l. 4-5).
Barta does not teach that the process thereby obtains a precipitated lignin oligomer, and that the process further comprises the step of c) obtaining precipitated lignin oligomer. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to use a step of purifying Barta’s oligomer by precipitation to modify Barta’s method. The proposed modification would read on the process thereby obtaining a precipitated lignin oligomer as claimed, and the process further comprising the step of: c) obtaining precipitated lignin oligomer as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for further purifying Barta’s oligomer in Barta’s method because Barta teaches that the method optionally further includes the step of purifying the oligomer using a method of purification (p. 7, l. 6-7), that the method optionally further includes the step of purifying the monomer using a method of purification (p. 6, l. 4-6), and that if necessary, the monomers can be further purified by any method known in the art, such as precipitation (p. 25, l. 8-10).
Regarding claim 3, Barta teaches that the method includes the step of depolymerizing at least one biopolymer from the biopolymer source into an oligomer within a system comprised of at least one solvent and at least one catalyst (p. 6, l. 9-11), that the at least one biopolymer is lignin (p. 5, l. 13-14; p. 6, l. 14-15), that the process of depolymerizing the biopolymer into a monomer is carried out over a period of time known as the reaction time (p. 24, l. 24-25), that as used herein, the term “reaction time” refers to an amount of time effective for the depolymerization of at least some biopolymers into monomers, mixtures of monomers, and/or oligomers (p. 24, l. 25-27), that the reaction time is between 0.1 hours to 10 hours (p. 24, l. 27-28), between 0.4 hours to 20 hours (p. 24, l. 28-29), at least 40 minutes (p. 24, l. 30-31), at least 60 minutes (p. 24, l. 31-32), at least 3 hours (p. 24, l. 32-33), at least 4 hours (p. 24, l. 33-34), at least 6 hours (p. 24, l. 34-p. 25, l. 1), at least 8 hours (p. 25, l. 1), at least 10 hours (p. 25, l. 1-2), at least 12 hours (p. 25, l. 2-3), at least 14 hours (p. 25, l. 3-4), at least 18 hours (p. 25, l. 4), or at least 20 hours (p. 25, l. 5), that the method optionally further includes the step of purifying the oligomer using a method of purification (p. 7, l. 6-7), that the method optionally further includes the step of purifying the monomer using a method of purification (p. 6, l. 4-6), and that if necessary, the monomers can be further purified by any method known in the art, such as precipitation (p. 25, l. 8-10), which suggests using a step of purifying Barta’s oligomer by precipitation of oligomer that is produced in Barta’s step of depolymerizing at least one biopolymer that is lignin from the biopolymer source into an oligomer to modify Barta’s method, and to continue Barta’s step of depolymerizing at least one biopolymer that is lignin from the biopolymer source into an oligomer for an amount of time after beginning the step of purifying Barta’s oligomer by precipitation of oligomer, which suggests wherein the thermal conversion in step b) is performed for greater than 0 h after precipitation of lignin oligomer starts.
Barta does not teach that the thermal conversion in step b) is performed for 3 to 7 h after precipitation of lignin oligomer starts. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to use a step of purifying Barta’s oligomer by precipitation of oligomer that is produced in Barta’s step of depolymerizing at least one biopolymer that is lignin from the biopolymer source into an oligomer to modify Barta’s method, and to continue Barta’s step of depolymerizing at least one biopolymer that is lignin from the biopolymer source into an oligomer for an amount of time that is optimized to be 3 hours to 7 hours after beginning the step of purifying Barta’s oligomer by precipitation of oligomer. The proposed modification would read on wherein the thermal conversion in step b) is performed for 3 to 7 h after precipitation of lignin oligomer starts as claimed. One of ordinary skill in the art would have been motivated to do so because purifying Barta’s oligomer by precipitation of oligomer that is produced in Barta’s step of depolymerizing at least one biopolymer that is lignin from the biopolymer source into an oligomer would have been beneficial for further purifying Barta’s oligomer in Barta’s method because Barta teaches that the method optionally further includes the step of purifying the oligomer using a method of purification (p. 7, l. 6-7), that the method optionally further includes the step of purifying the monomer using a method of purification (p. 6, l. 4-6), and that if necessary, the monomers can be further purified by any method known in the art, such as precipitation (p. 25, l. 8-10). Also, one of ordinary skill in the art would have been motivated to continue Barta’s step of depolymerizing at least one biopolymer that is lignin from the biopolymer source into an oligomer for an amount of time that is optimized to be 3 hours to 7 hours after beginning the step of purifying Barta’s oligomer by precipitation of oligomer because it would have been beneficial for optimizing the extent of depolymerizing at least one biopolymer that is lignin from the biopolymer source into an oligomer while also purifying oligomer that is produced in Barta’s method because Barta teaches that the method includes the step of depolymerizing at least one biopolymer from the biopolymer source into an oligomer within a system comprised of at least one solvent and at least one catalyst (p. 6, l. 9-11), that the at least one biopolymer is lignin (p. 5, l. 13-14; p. 6, l. 14-15), that as used herein, the term “reaction time” refers to an amount of time effective for the depolymerization of at least some biopolymers into monomers, mixtures of monomers, and/or oligomers (p. 24, l. 25-27), that the reaction time is between 0.1 hours to 10 hours (p. 24, l. 27-28), between 0.4 hours to 20 hours (p. 24, l. 28-29), at least 40 minutes (p. 24, l. 30-31), at least 60 minutes (p. 24, l. 31-32), at least 3 hours (p. 24, l. 32-33), at least 4 hours (p. 24, l. 33-34), at least 6 hours (p. 24, l. 34-p. 25, l. 1), at least 8 hours (p. 25, l. 1), at least 10 hours (p. 25, l. 1-2), at least 12 hours (p. 25, l. 2-3), at least 14 hours (p. 25, l. 3-4), at least 18 hours (p. 25, l. 4), or at least 20 hours (p. 25, l. 5), that the method optionally further includes the step of purifying the oligomer using a method of purification (p. 7, l. 6-7), that the method optionally further includes the step of purifying the monomer using a method of purification (p. 6, l. 4-6), and that if necessary, the monomers can be further purified by any method known in the art, such as precipitation (p. 25, l. 8-10), which means that an amount of time in hours for which Barta’s step of depolymerizing at least one biopolymer that is lignin from the biopolymer source into an oligomer is continued after beginning the step of purifying Barta’s oligomer by precipitation of oligomer would have affected the extent of depolymerizing at least one biopolymer that is lignin from the biopolymer source into an oligomer.
Regarding claim 4, Barta teaches that the method includes the step of depolymerizing at least one biopolymer from the biopolymer source into a monomer within a system comprised of at least one solvent and at least one catalyst (p. 5, l. 8-10) or includes the step of depolymerizing at least one biopolymer from the biopolymer source into an oligomer within a system comprised of at least one solvent and at least one catalyst (p. 6, l. 9-11), that the at least one biopolymer is lignin (p. 5, l. 13-14; p. 6, l. 14-15), that the solvent is optionally a mixture of water and at least one organic solvent (p. 20, l. 4-5), that non-limiting examples of organic solvents include methanol, ethanol, and isopropanol (p. 20, l. 1-2), that the catalyst loading of a catalyst is from about 0.05 weight percent to about 60 weight percent based on the weight of the biopolymer (p. 23, l. 1-3), and that in an example, the amount of methanol is 500 ml, the amount of finely ground candlenut shells is 110 g (p. 27, l. 25-26), which reads on wherein the mixture that is optionally the aqueous mixture and comprises greater than 0 wt.-% and less than 100 wt.-% lignin, greater than 0 wt.-% and less than 100 wt.-% catalyst, greater than or equal to 0 wt.-% and less than 100 wt.-% base, and greater than or equal to 0 wt.-% and less than 100 wt.-% primary C1 to C3-alcohol, based on the total weight of the aqueous mixture.
Barta does not teach that the aqueous mixture comprises 5 to 25 wt.-% lignin, based on the total weight of the aqueous 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 Barta’s lignin in Barta’s system to be from 5 weight percent to 25 weight percent, based on the weight of Barta’s system. The proposed modification would read on wherein the aqueous mixture comprises 5 to 25 wt.-% lignin, based on the total weight of the aqueous 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 extent of depolymerization of Barta’s lignin in Barta’s method because Barta teaches that the method includes the step of depolymerizing at least one biopolymer from the biopolymer source into a monomer within a system comprised of at least one solvent and at least one catalyst (p. 5, l. 8-10) or includes the step of depolymerizing at least one biopolymer from the biopolymer source into an oligomer within a system comprised of at least one solvent and at least one catalyst (p. 6, l. 9-11), that the at least one biopolymer is lignin (p. 5, l. 13-14; p. 6, l. 14-15), that the catalyst loading of a catalyst is from about 0.05 weight percent to about 60 weight percent based on the weight of the biopolymer (p. 23, l. 1-3), and that in an example, the amount of methanol is 500 ml, the amount of finely ground candlenut shells is 110 g (p. 27, l. 25-26), which means that the amount of Barta’s lignin in Barta’s system in weight percent, based on the weight of Barta’s system, would have affected an extent of depolymerization of Barta’s lignin in Barta’s method.
Barta does not teach that the aqueous mixture further comprises 0.01 to 1.0 wt.-% catalyst, based on the total weight of the aqueous 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 Barta’s catalyst in Barta’s system to be from 0.01 weight percent to 1.0 weight percent, based on the weight of Barta’s system. The proposed modification would read on wherein the aqueous mixture further comprises 0.01 to 1.0 wt.-% catalyst, based on the total weight of the aqueous 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 extent of catalysis of depolymerization of lignin in Barta’s method because Barta teaches that the method includes the step of depolymerizing at least one biopolymer from the biopolymer source into a monomer within a system comprised of at least one solvent and at least one catalyst (p. 5, l. 8-10) or includes the step of depolymerizing at least one biopolymer from the biopolymer source into an oligomer within a system comprised of at least one solvent and at least one catalyst (p. 6, l. 9-11), that the at least one biopolymer is lignin (p. 5, l. 13-14; p. 6, l. 14-15), that the catalyst is a catalyst for depolymerization (p. 20, l. 10-11), that the catalyst loading of a catalyst is form about 0.05 weight percent to about 60 weight percent based on the weight of the biopolymer (p. 23, l. 1-3), and that in an example, the amount of methanol is 500 ml, the amount of finely ground candlenut shells is 110 g (p. 27, l. 25-26), which means that the amount of Barta’s catalyst in Barta’s system in weight percent, based on the weight of Barta’s system, would have affected an extent of catalysis of depolymerization of lignin in Barta’s method.
Barta does not teach a specific embodiment in which the mixture is the aqueous mixture and further comprises 5 to 45 wt.-% primary C1 to C4-alcohol, based on the total weight of the aqueous mixture. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to select Barta’s mixture of water and at least one organic solvent that is methanol, ethanol, or isopropanol as Barta’s at least one solvent in Barta’s method, and to optimize the amount of Barta’s at least one organic solvent that is methanol, ethanol, or isopropanol in Barta’s system to be from 5 weight percent to 45 weight percent, based on the weight of Barta’s system. The proposed modification would read on the mixture is the aqueous mixture and further comprises 5 to 45 wt.-% primary C1, C1, or C3-alcohol, based on the total weight of the aqueous mixture as claimed. One of ordinary skill in the art would have been motivated to select Barta’s mixture of water and at least one organic solvent that is methanol, ethanol, or isopropanol as Barta’s at least one solvent in Barta’s method because it would have been beneficial for modifying an extent of solubility of Barta’s biopolymer in Barta’s solvent and/or for providing a species of solvent that is suitable for Barta’s method because Barta teaches that as would be understood by one skill in the art, any solvent in which the biopolymer is soluble is contemplated (p. 19, l. 32-33), that the system is optionally comprised of at least two solvents (p. 19, l. 31-32), that the solvent is optionally a mixture of water and at least one organic solvent (p. 20, l. 4-5), that non-limiting examples of organic solvents include methanol, ethanol, and isopropanol (p. 20, l. 1-2), that the method includes the step of depolymerizing at least one biopolymer from the biopolymer source into a monomer within a system comprised of at least one solvent and at least one catalyst (p. 5, l. 8-10) or includes the step of depolymerizing at least one biopolymer from the biopolymer source into an oligomer within a system comprised of at least one solvent and at least one catalyst (p. 6, l. 9-11), that the use of sequential extractions and/or fractionations permits the separation of biopolymers with different properties, such as average molecular weights, different chain lengths, polarity, or chemical functionality, based on the solubility of each biopolymer in the solvent(s) (p. 18, l. 26-29), and that the at least one biopolymer is lignin (p. 5, l. 13-14; p. 6, l. 14-15). Also, one of ordinary skill in the art would have been motivated to optimize the amount of Barta’s at least one organic solvent that is methanol, ethanol, or isopropanol in Barta’s system in weight percent, based on the weight of Barta’s system, because it would have been beneficial for optimizing processability of Barta’s system and for optimizing an extent of depolymerization of lignin in Barta’s method because Barta teaches that the method includes the step of depolymerizing at least one biopolymer from the biopolymer source into a monomer within a system comprised of at least one solvent and at least one catalyst (p. 5, l. 8-10) or includes the step of depolymerizing at least one biopolymer from the biopolymer source into an oligomer within a system comprised of at least one solvent and at least one catalyst (p. 6, l. 9-11), that the at least one biopolymer is lignin (p. 5, l. 13-14; p. 6, l. 14-15), that the solvent is optionally a mixture of water and at least one organic solvent (p. 20, l. 4-5), that non-limiting examples of organic solvents include methanol, ethanol, and isopropanol (p. 20, l. 1-2), and that in an example, the amount of methanol is 500 ml, the amount of finely ground candlenut shells is 110 g (p. 27, l. 25-26), which means that the amount of Barta’s at least one organic solvent that is methanol, ethanol, or isopropanol in Barta’s system in weight percent, based on the weight of Barta’s system, would have affected processability of Barta’s system and an extent of depolymerization of lignin in Barta’s method.
Barta does not teach that the aqueous mixture further comprises 1 to 5 wt.-% base, based on the total weight of the aqueous mixture. However, Van Es teaches lignin depolymerization by placing mixed wheat straw and grass soda lignin and demineralized water in a reactor, adding catalyst, adjusting the pH of the resulting suspension to above pH 10 by adding aqueous sodium hydroxide, closing the reactor, stirring, heating the reactor to a desired temperature, after reaction, and rapidly cooling the reactor down to room temperature using a water bath (p. 11, l. 15-24). Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to use a step of adjusting the pH of Barta’s system to above pH 10 by adding Van Es’s aqueous sodium hydroxide to Barta’s system to modify Barta’s method, and to optimize the amount of Van Es’s sodium hydroxide in Barta’s system to be from 1 weight percent to 5 weight percent, based on the weight of Barta’s system. The proposed modification would read on wherein the aqueous mixture further comprises 1 to 5 wt.-% base, based on the total weight of the aqueous mixture as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for completely dissolving Barta’s lignin in Barta’s system and for optimizing complete dissolution of Barta’s lignin in Barta’s system in Barta’s method because Van Es teaches lignin depolymerization by placing mixed wheat straw and grass soda lignin and demineralized water in a reactor, adding catalyst, adjusting the pH of the resulting suspension to above pH 10 by adding aqueous sodium hydroxide, wherein above pH 10 the lignin was completely dissolved, closing the reactor, stirring, heating the reactor to a desired temperature, after reaction, and rapidly cooling the reactor down to room temperature using a water bath (p. 11, l. 15-24), and because completely dissolving Barta’s lignin in Barta’s system would have been desirable for Barta’s method because it would have improved uniformity of Barta’s depolymerization at least one biopolymer that is lignin because Barta teaches that the method includes the step of depolymerizing at least one biopolymer from the biopolymer source into a monomer within a system comprised of at least one solvent and at least one catalyst (p. 5, l. 8-10), or includes the step of depolymerizing at least one biopolymer from the biopolymer source into an oligomer within a system comprised of at least one solvent and at least one catalyst (p. 6, l. 9-11), that the at least one biopolymer is lignin (p. 5, l. 13-14; p. 6, l. 14-15), that the solvent is optionally a mixture of water and at least one organic solvent (p. 20, l. 4-5), that the catalyst loading of a catalyst is from about 0.05 weight percent to about 60 weight percent based on the weight of the biopolymer (p. 23, l. 1-3), and that in an example, the amount of methanol is 500 ml, the amount of finely ground candlenut shells is 110 g (p. 27, l. 25-26), which means that the amount of Van Es’s sodium hydroxide in Barta’s system in weight percent, based on the weight of Barta’s system, would have affected complete dissolution of Barta’s lignin in Barta’s system in Barta’s method.
Regarding claim 5, Barta teaches that the system is optionally heated in a temperature range from 30 °C to 500 °C (p. 23, l. 27-28), that pressure is optionally applied to the system (p. 24, l. 6), that the pressure can be any pressure that is sufficient to promote the depolymerization of a biopolymer (p. 24, l. 6-7), that a gas is optionally added to the system to increase the pressure (p. 24, l. 8-9), that non-limiting examples of a gas include nitrogen, argon, and hydrogen (p. 24, l. 9-10), and that the initial pressure of the system at room temperature is between 10 bar and 400 bar (p. 24, l. 11-12), or between 0.1 bar and 100 bar (p. 24, l. 12-13), which reads on wherein conversion that is optionally conversion is conducted at 10 to 400 bar or at 0.1 bar to 100 bar at reaction temperature of 30°C to 500°C.
Barta does not teach a specific embodiment wherein thermal conversion is conducted at reaction temperature of 280°C to 400°C. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to use a step of heating Barta’s system to a temperature range that is optimize to be from 280 °C to 400 °C to modify Barta’s method. The proposed modification would read on wherein thermal conversion is conducted at reaction temperature of 280°C to 400°C 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 ability of Barta’s method to depolymerize lignin and for optimizing an extent of depolymerization of Barta’s lignin in Barta’s method because Barta teaches that the system is optionally heated in a temperature range from 30 °C to 500 °C (p. 23, l. 27-28), that the method includes the step of depolymerizing at least one biopolymer from the biopolymer source into a monomer within a system comprised of at least one solvent and at least one catalyst (p. 5, l. 8-10) or includes the step of depolymerizing at least one biopolymer from the biopolymer source into an oligomer within a system comprised of at least one solvent and at least one catalyst (p. 6, l. 9-11), and that the at least one biopolymer is lignin (p. 5, l. 13-14; p. 6, l. 14-15), which means that the temperature range to which Barta’s system is heated in Barta’s method would have affected an extent of depolymerization of Barta’s lignin in Barta’s method.
Barta does not teach a specific embodiment wherein thermal conversion is conducted at 80 to 150 bar. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to use Barta’s step of applying pressure to Barta’s system by adding gas that is nitrogen, argon, or hydrogen to increase the pressure to a pressure that is optimized to be from 80 bar to 150 bar to modify Barta’s method. The proposed modification would read on wherein thermal conversion is conducted at 80 to 150 bar as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for promoting depolymerization of lignin in Barta’s method and for optimizing an extent of depolymerization of lignin in Barta’s method because Barta teaches that pressure is optionally applied to the system (p. 24, l. 6), that a gas is optionally added to the system to increase the pressure (p. 24, l. 8-9), that the pressure can be any pressure that is sufficient to promote the depolymerization of a biopolymer (p. 24, l. 6-7), that non-limiting examples of a gas include nitrogen, argon, and hydrogen (p. 24, l. 9-10), that the initial pressure of the system at room temperature is between 10 bar and 400 bar (p. 24, l. 11-12), or between 0.1 bar and 100 bar (p. 24, l. 12-13), that the method includes the step of depolymerizing at least one biopolymer from the biopolymer source into a monomer within a system comprised of at least one solvent and at least one catalyst (p. 5, l. 8-10) or includes the step of depolymerizing at least one biopolymer from the biopolymer source into an oligomer within a system comprised of at least one solvent and at least one catalyst (p. 6, l. 9-11), and that the at least one biopolymer is lignin (p. 5, l. 13-14; p. 6, l. 14-15), which means that the pressure in bar in Barta’s system in Barta’s method would have affected an extent of depolymerization of lignin in Barta’s method.
Regarding claim 6, Barta teaches that the system is comprised of at least one solvent and at least one catalyst (p. 5, l. 8-10; p. 6, l. 9-11), that the catalyst is optionally a heterogenous catalyst (p. 20, l. 12), that examples of heterogeneous catalysts includes, but are not limited to Co, Cu, Ni, Pt, Ru, or combinations of these metals supported on aluminum oxide (p. 20, l. 12-14), that the catalyst is optionally copper (II) oxide on alumina (p. 20, l. 19-20), that the catalyst is optionally a hydrogenation catalyst (p. 22, l. 9-10), and that non-limiting examples of hydrogenation catalysts include nickel, copper, cobalt, nickel, ruthenium, platinum, copper (II) oxide, or combinations thereof (p. 22, l. 10-14), which optionally reads on wherein the catalyst selected from Ru, Cu, Co, Ni, Pt, oxides of said metals, and mixtures thereof as claimed.
Barta does not teach a specific embodiment wherein the catalyst selected from the group consisting of Ru, Cu, Co, Ni, Pt, sulfides of said metals, oxides of said metals, and mixtures thereof. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to select Barta’s heterogeneous catalyst that is Co, Cu, Ni, Pt, Ru, combinations of these metals supported on aluminum oxide, or copper (II) oxide on alumina or Barta’s hydrogenation catalyst that is nickel, copper, cobalt, nickel, ruthenium, platinum, copper (II) oxide, or combinations thereof as Barta’s at least one catalyst. The proposed modification would read on wherein the catalyst selected from Ru, Cu, Co, Ni, Pt, oxides of said metals, and mixtures thereof as claimed. One of ordinary skill in art would have been motivated to do so because it would have been beneficial for modifying catalytic properties in Barta’s method, for modifying an ability of Barta’s at least one catalyst to catalyze Barta’s method, and/or for providing a species of catalyst that is suitable for the catalyst in Barta’s method because Barta teaches that the system is comprised of at least one solvent and at least one catalyst (p. 5, l. 8-10; p. 6, l. 9-11), that the catalyst is optionally a heterogenous catalyst (p. 20, l. 12), that examples of heterogeneous catalysts includes, but are not limited to Co, Cu, Ni, Pt, Ru, or combinations of these metals supported on aluminum oxide (p. 20, l. 12-14), that the catalyst is optionally copper (II) oxide on alumina (p. 20, l. 19-20), that the catalyst is optionally a hydrogenation catalyst (p. 22, l. 9-10), and that non-limiting examples of hydrogenation catalysts include nickel, copper, cobalt, nickel, ruthenium, platinum, copper (II) oxide, or combinations thereof (p. 22, l. 10-14).
Regarding claim 7, Barta teaches that the solvent is optionally a mixture of water and at least one organic solvent (p. 20, l. 4-5), and that non-limiting examples of organic solvents include methanol and ethanol (p. 20, l. 1-2), which optionally reads on wherein the primary alcohol is selected from MeOH and EtOH, as claimed.
Barta does not teach a specific embodiment wherein the primary alcohol is selected from the claimed group. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to select Barta’s mixture of water and at least one organic solvent that is methanol or ethanol as Barta’s at least one solvent in Barta’s method. The proposed modification would read on wherein the primary alcohol is selected from MeOH and EtOH, 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 solubility of Barta’s biopolymer in Barta’s solvent and/or for providing a species of solvent that is suitable for Barta’s method because Barta teaches that as would be understood by one skill in the art, any solvent in which the biopolymer is soluble is contemplated (p. 19, l. 32-33), that the system is optionally comprised of at least two solvents (p. 19, l. 31-32), that the solvent is optionally a mixture of water and at least one organic solvent (p. 20, l. 4-5), that non-limiting examples of organic solvents include methanol and ethanol (p. 20, l. 1-2), that the method includes the step of depolymerizing at least one biopolymer from the biopolymer source into a monomer within a system comprised of at least one solvent and at least one catalyst (p. 5, l. 8-10) or includes the step of depolymerizing at least one biopolymer from the biopolymer source into an oligomer within a system comprised of at least one solvent and at least one catalyst (p. 6, l. 9-11), that the use of sequential extractions and/or fractionations permits the separation of biopolymers with different properties, such as average molecular weights, different chain lengths, polarity, or chemical functionality, based on the solubility of each biopolymer in the solvent(s) (p. 18, l. 26-29), and that the at least one biopolymer is lignin (p. 5, l. 13-14; p. 6, l. 14-15).
Regarding claim 8, Barta teaches that pressure is optionally applied to the system (p. 24, l. 6), that a gas is optionally added to the system to increase the pressure (p. 24, l. 8-9), and that non-limiting examples of a gas include nitrogen, argon, and hydrogen (p. 24, l. 9-10), which optionally reads on whereon the non-oxidizing gas is N2, argon, or H2 as claimed.
Barta does not teach a specific embodiment wherein the non-oxidizing gas is N2, argon, and/or H2. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to use Barta’s step of applying pressure to Barta’s system by adding gas that is nitrogen, argon, or hydrogen to increase the pressure to modify Barta’s method. The proposed modification would read on whereon the non-oxidizing gas is N2, argon, or H2 as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for promoting depolymerization of lignin in Barta’s method because Barta teaches that pressure is optionally applied to the system (p. 24, l. 6), that a gas is optionally added to the system to increase the pressure (p. 24, l. 8-9), that the pressure can be any pressure that is sufficient to promote the depolymerization of a biopolymer (p. 24, l. 6-7), that non-limiting examples of a gas include nitrogen, argon, and hydrogen (p. 24, l. 9-10), that the method includes the step of depolymerizing at least one biopolymer from the biopolymer source into a monomer within a system comprised of at least one solvent and at least one catalyst (p. 5, l. 8-10) or includes the step of depolymerizing at least one biopolymer from the biopolymer source into an oligomer within a system comprised of at least one solvent and at least one catalyst (p. 6, l. 9-11), and that the at least one biopolymer is lignin (p. 5, l. 13-14; p. 6, l. 14-15).
Regarding claim 9, Barta teaches that the Mn of the lignin produced in the method is 385, 375, 402, 378, 366, 367, 390, or 395 g/mol (p. 36, l. 24-p. 37, l. 1), which reads on wherein the process provides lignin oligomers having a molecular weight of 385, 375, 402, 378, 366, 367, 390, or 395 g/mol as claimed.
Regarding claim 10, the Office recognizes that all of the claimed physical properties are not positively taught by Barta, namely wherein the process provides precipitated lignin oligomers having an oxygen content of less than 20 wt.-% based on the total weight of the precipitated oligomers. However, Barta in view of Van Es renders obvious all of the claimed ingredients, amounts, process steps, and process conditions of the process according to claims 1, 2, and 4-9 and that the process further comprises the step of c) obtaining precipitated lignin oligomer as explained above. Furthermore, the specification of the instant application recites that the process according to the present invention provides lignin oligomers having an oxygen con- tent of less than 20 wt.-% based on the total weight of the lignin oligomers (p. 7, l. 12-13). Therefore, the claimed physical properties would naturally arise from the process that is rendered obvious by Barta in view of Van Es. When the structure recited in the reference is substantially identical to that of the claims, claimed properties or functions are presumed to be inherent (MPEP 2112.01(I)). If the prior art teaches the identical chemical structure, the properties applicant discloses and/or claims are necessarily present (MPEP 2112.01(II)). If it is the applicant’s position that this would not be the case: (1) evidence would need to be presented 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 as to how to obtain the claimed properties with only the claimed ingredients, amounts, process steps, and process conditions.
Regarding claim 11, the limitation “wherein the catalyst, base, primary alcohol and/or unconverted lignin can be reintroduced in the process for depolymerization of lignin either in a batch or continuous process” is interpreted as “wherein the catalyst, base, primary alcohol, and/or unconverted lignin are capable of being reintroduced in the process for depolymerization of lignin either in a batch or continuous process”. Since Barta in view of Van Es renders obvious all of the claimed ingredients, amounts, process steps, and process conditions of the catalyst, base, primary alcohol, and lignin in the process according to claims 1, 2, and 4-10 ,the catalyst, base, primary alcohol, and/or unconverted lignin in the process that is rendered obvious by Barta in view of Van Es would have been capable of being reintroduced in the process for depolymerization of lignin either in a batch or continuous process. Therefore, Barta in view of Van Es renders obvious wherein the catalyst, base, primary alcohol, and/or unconverted lignin can be reintroduced in the process for depolymerization of lignin either in a batch or continuous process as claimed.
Claim 12 is rejected under 35 U.S.C. 103 as being unpatentable over Barta et al. (WO 2014/201325 A2, cited in IDS, made of record on 05/31/2022) in view of Van Es et al. (WO 2014/168473 A1, cited in IDS, made of record on 08/05/2022) as applied to claim 2, and further in view of Massey-Brooker et al. (US 2016/0374922 A1).
Regarding claim 12, Barta in view of Van Es renders obvious the process according to claim 2 as explained above.
Barta does not teach that the depolymerized lignin-oligomer is further converted to polymers. However, Massey-Brooker teaches a cross-linked co-polymer of a lignin oligomer and a vinyl monomer [0004] that is prepared by reacting a lignin oligomer with a vinyl monomer [0063]. Barta and Massey-Brooker are analogous art because both references are in the same field of endeavor of a method that uses lignin. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to react Massey-Brooker’s vinyl monomer with Barta’s oligomer that is prepared by Barta’s method that includes the step of depolymerizing at least one biopolymer that is lignin from the biopolymer source into an oligomer within a system comprised of at least one solvent and at least one catalyst to prepare a cross-linked co-polymer of Barta’s oligomer and Massey-Brooker’s vinyl monomer. The proposed modification would read on wherein the depolymerized lignin-oligomer is further converted to polymers as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for providing a utility for Barta’s oligomer and for modifying mechanical properties of the oligomer due to the cross-linking because Massey-Brooker teaches that reacting a lignin oligomer with a vinyl monomer [0063] is beneficial for preparing a cross-linked co-polymer of a lignin oligomer and a vinyl monomer [0004], and because Barta teaches that the method includes the step of depolymerizing at least one biopolymer from the biopolymer source into an oligomer within a system comprised of at least one solvent and at least one catalyst (p. 6, l. 9-11), and that the at least one biopolymer is lignin (p. 5, l. 13-14; p. 6, l. 14-15).
Claims 12 and 13 are rejected under 35 U.S.C. 103 as being unpatentable over Barta et al. (WO 2014/201325 A2, cited in IDS, made of record on 05/31/2022) in view of Van Es et al. (WO 2014/168473 A1, cited in IDS, made of record on 08/05/2022) as applied to claim 2, and further in view of Qiu et al. (CN 109485824 A, machine translation in English used for citation).
Regarding claims 12 and 13, Barta in view of Van Es renders obvious the process according to claim 2 as explained above.
Barta does not teach that the depolymerized lignin-oligomer is further converted to polymers and that the depolymerized lignin-oligomer is further converted to polymers selected from the group consisting of polyesters, polyurethanes, polyamides, and mixtures thereof. However, Qiu teaches obtaining a recyclable thermosetting lignin-based polyurethane elastomer by reacting a polyurethane prepolymer with a partially depolymerized lignin (p. 4, l. 35-36; p. 6, l. 10-18). Barta and Qiu are analogous art because both references are in the same field of endeavor of a process for depolymerization of lignin. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to react Qiu’s polyurethane prepolymer with Barta’s oligomer that is prepared by Barta’s method that includes the step of depolymerizing at least one biopolymer that is lignin from the biopolymer source into an oligomer within a system comprised of at least one solvent and at least one catalyst to obtain a recyclable thermosetting lignin-based polyurethane elastomer. The proposed modification would read on wherein the depolymerized lignin-oligomer is further converted to polymers as claimed, wherein the depolymerized lignin-oligomer is further converted to polymers selected from polyurethanes as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for providing a utility for Barta’s oligomer and for modifying elastomeric properties of the oligomer because Qiu teaches obtaining a recyclable thermosetting lignin-based polyurethane elastomer by reacting a polyurethane prepolymer with a partially depolymerized lignin (p. 4, l. 35-36; p. 6, l. 10-18), and because Barta teaches that the method includes the step of depolymerizing at least one biopolymer from the biopolymer source into an oligomer within a system comprised of at least one solvent and at least one catalyst (p. 6, l. 9-11), and that the at least one biopolymer is lignin (p. 5, l. 13-14; p. 6, l. 14-15).
Claim 14 is rejected under 35 U.S.C. 103 as being unpatentable over Barta et al. (WO 2014/201325 A2, cited in IDS, made of record on 05/31/2022) in view of Van Es et al. (WO 2014/168473 A1, cited in IDS, made of record on 08/05/2022) as applied to claim 2, and further in view of Cheng et al. (Cheng et al., “Producing jet fuel from biomass lignin: Potential pathways to alkyl-benzenes and cycloalkanes”, Renewable and Sustainable Energy Reviews, 2017, vol. 72, p. 673-722, cited in IDS, made of record 08/05/2022).
Regarding claim 14, Barta in view of Van Es renders obvious the process according to claim 2 as explained above.
Barta does not teach that the depolymerized lignin-oligomer is further converted to bio-based aromatics selected from the group consisting of toluene, benzene, xylenes, and mixtures thereof. However, Cheng teaches catalytic fast pyrolysis of kraft lignin that yields benzene, toluene, and xylene (p. 680), HDO of low-molecular-weight oxy-compounds from lignin degradation that leaves BTX as the primary products (p. 686), wherein HDO is hydrodeoxygenation (p. 673), wherein BTX is benzene, toluene, and xylene (p. 673), hydrodeoxygenation of lignin-derived oxy-compounds to BTX (p. 691), converting biomass into aromatic hydrocarbons that include BTX compounds (p. 700), and a combination of depolymerization and HDO steps that directly produce benzene, toluene, and xylenes, wherein the depolymerization is lignin depolymerization (p. 710), wherein the HDO is hydrodeoxygenation (p. 673). Cheng teaches that lignin depolymerization includes breaking C-C and C-O-C bonds, and hydrogenating unsaturated bonds in lignin oligomers (p. 679). Barta and Cheng are analogous art because both references are in the same field of endeavor of a process for depolymerization of lignin. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to use a step of catalytic fast pyrolysis of Barta’s oligomer that yields benzene, toluene, and xylene, a step of hydrodeoxygenation of Barta’s oligomer that leaves benzene, toluene, and xylene as products, a step of converting Barta’s oligomer into aromatic hydrocarbons that include benzene, toluene, and xylene, or a combination of depolymerization of lignin and hydrodeoxygenation steps that directly produce benzene, toluene, and xylenes to modify Barta’s method. The proposed modification would read on wherein the depolymerized lignin-oligomer is further converted to bio-based aromatics selected from the group consisting of toluene, benzene, xylenes, and mixtures thereof as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for providing a utility of Barta’s oligomer that is produced in Barta’s method and for producing toluene, benzene, and xylene because Cheng teaches catalytic fast pyrolysis of kraft lignin that yields benzene, toluene, and xylene (p. 680), HDO of low-molecular-weight oxy-compounds from lignin degradation that leaves BTX as the primary products (p. 686), wherein HDO is hydrodeoxygenation (p. 673), wherein BTX is benzene, toluene, and xylene (p. 673), hydrodeoxygenation of lignin-derived oxy-compounds to BTX (p. 691), converting biomass into aromatic hydrocarbons that include BTX compounds (p. 700), and a combination of depolymerization and HDO steps that directly produce benzene, toluene, and xylenes, wherein the depolymerization is lignin depolymerization (p. 710), wherein the HDO is hydrodeoxygenation (p. 673). Which would have been desirable for modifying Barta’s method because Barta teaches that the method includes the step of depolymerizing at least one biopolymer from the biopolymer source into an oligomer within a system comprised of at least one solvent and at least one catalyst (p. 6, l. 9-11), and that the at least one biopolymer is lignin (p. 5, l. 13-14; p. 6, l. 14-15).
Response to Arguments
Applicant’s arguments, see p. 5, filed 02/17/2026, with respect to the objection to claims 2-14 have been fully considered and are persuasive. The objection to claims 2-14 has been withdrawn.
Applicant's arguments filed 02/17/2026 have been fully considered but they are not persuasive. In response to the applicant’s argument that Barta is deficient regarding five aspects with respect to present claim 1, that these five aspects define the claimed process and relate to particular process conditions for temperature, aqueous mixtures including a primary alcohol, a non-oxidizing atmosphere, pH, and a precipitated lignin oligomer, and that Barta is acknowledged as lacking each of the claimed process conditions (p. 5-6), although the Office acknowledges that Barta does not teach the claimed process conditions for temperature, aqueous mixtures including a primary alcohol, a non-oxidizing atmosphere, pH, and a precipitated lignin oligomer, the combination of Barta in view of Van Es provides motivation for one of ordinary skill in the art to have found it obvious, before the effective filing date of the claimed invention, to modify Barta’s process conditions for temperature, aqueous mixtures including a primary alcohol, a non-oxidizing atmosphere, pH, and a precipitated lignin oligomer. One of ordinary skill in the art would have been motivated to modify these process conditions because it would have been beneficial for modifying an ability of Barta’s method to depolymerize lignin, for optimizing an extent of depolymerization of Barta’s lignin in Barta’s method, for modifying an extent of solubility of Barta’s biopolymer in Barta’s solvent and/or for providing a species of solvent that is suitable for Barta’s method, for promoting depolymerization of lignin in Barta’s method, for completely dissolving Barta’s lignin in Barta’s system, and for further purifying Barta’s oligomer in Barta’s method, as explained in the rejection of claims 1 and 2 that is set forth in this Office action. Furthermore, one of ordinary skill in the art would have been motivated to modify these process conditions because it would have been beneficial for making Barta’s method more effective at depolymerizing lignin into an oligomer and purifying the oligomer.
In response to the applicant’s argument that a person having ordinary skill in the art would not have arrived at the present claims in view of Barta, which is deficient for each and every claimed process condition, and that at most, Barta could have motivated a person having ordinary skill in the art to perform its process, rather than a separate process defined by the claimed process condition (p. 6-7), the rejection of claim 1 is not based on Barta individually. The rejection of claim 1 is based on the combination of Barta in view of Van Es to rendering it obvious to modify Barta’s process conditions and obtain each and every process condition as claimed. One cannot show nonobviousness by attacking references individually where the rejections are based on combinations of references. See In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981); In re Merck & Co., 800 F.2d 1091, 231 USPQ 375 (Fed. Cir. 1986). The combination of Barta in view of Van Es provides motivation for one of ordinary skill in the art to have found it obvious, before the effective filing date of the claimed invention, to modify Barta’s process conditions and obtain each and every process condition as claimed, as explained in the rejection of claims 1 and 2 that is set forth in this Office action. Furthermore, one of ordinary skill in the art would have been motivated to modify these process conditions because it would have been beneficial for making Barta’s method more effective at depolymerizing lignin into an oligomer and purifying the oligomer.
In response to the applicant’s argument that there is not teaching, suggestion, motivation, or other reason in Barta and Van Es to modify Barta, without guidance, as asserted by the Office (p. 7), the Office recognizes that obviousness may be established by combining or modifying the teachings of the prior art to produce the claimed invention where there is some teaching, suggestion, or motivation to do so found either in the references themselves or in the knowledge generally available to one of ordinary skill in the art. See In re Fine, 837 F.2d 1071, 5 USPQ2d 1596 (Fed. Cir. 1988), In re Jones, 958 F.2d 347, 21 USPQ2d 1941 (Fed. Cir. 1992), and KSR International Co. v. Teleflex, Inc., 550 U.S. 398, 82 USPQ2d 1385 (2007). In this case, one of ordinary skill in the art would have been motivated to modify these process conditions of Barta’s method because it would have been beneficial for modifying an ability of Barta’s method to depolymerize lignin, for optimizing an extent of depolymerization of Barta’s lignin in Barta’s method, for modifying an extent of solubility of Barta’s biopolymer in Barta’s solvent and/or for providing a species of solvent that is suitable for Barta’s method, for promoting depolymerization of lignin in Barta’s method, for completely dissolving Barta’s lignin in Barta’s system, and for further purifying Barta’s oligomer in Barta’s method, as explained in the rejection of claims 1 and 2 that is set forth in this Office action. Furthermore, one of ordinary skill in the art would have been motivated to modify these process conditions because it would have been beneficial for making Barta’s method more effective at depolymerizing lignin into an oligomer and purifying the oligomer.
In response to the applicant’s argument that impermissible hindsight would have been required to modify Barta as asserted by the Office (p. 7), it must be recognized that any judgment on obviousness is in a sense necessarily a reconstruction based upon hindsight reasoning. But so long as it takes into account only knowledge which was within the level of ordinary skill at the time the claimed invention was made, and does not include knowledge gleaned only from the applicant's disclosure, such a reconstruction is proper. See In re McLaughlin, 443 F.2d 1392, 170 USPQ 209 (CCPA 1971). The Office’s judgment on obviousness that is set forth in this Office action takes into account only the teachings of Barta and Van Es and the knowledge of one of ordinary skill in the art before the effective filing date of the claimed invention.
In response to the applicant’s argument that the Office based on the rejections in part on “the only claims that require that a lignin oligomer is obtained as a precipitate are claims 2-14” in page 31 of the Office action dated 11/25/25 (p. 7), the previous Office action was not the Office action mailed on 11/25/2025. The previous Office action was mailed on 02/02/2026, and the Office action did not state that he only claims that require that a lignin oligomer is obtained as a precipitate are claims 2-14.
In response to the applicant’s argument that claim 1 amended for clarity and precision to recite that the method results in obtaining a precipitated lignin oligomer (p. 7), the amendment to claim 1 filed on 02/17/2026 that recites “thereby obtaining a precipitated lignin oligomer” was also present in claim 1 filed on 01/23/2026. The Office entered that claim amendment and rejected the claims as set forth in the Advisory Action mailed on 02/02/2026,
In response to the applicant’s argument that Barta and Van Es do not teach or suggest the combination of elements as presently claimed (p. 7), the combination of Barta in view of Van Es provides motivation for one of ordinary skill in the art to have found it obvious, before the effective filing date of the claimed invention, to modify Barta’s process conditions for temperature, aqueous mixtures including a primary alcohol, a non-oxidizing atmosphere, pH, and a precipitated lignin oligomer and arrive at the combination of elements as presently claimed, as explained in the rejection of claims 1 and 2 that is set forth in this Office action. One of ordinary skill in the art would have been motivated to modify these process conditions because it would have been beneficial for modifying an ability of Barta’s method to depolymerize lignin, for optimizing an extent of depolymerization of Barta’s lignin in Barta’s method, for modifying an extent of solubility of Barta’s biopolymer in Barta’s solvent and/or for providing a species of solvent that is suitable for Barta’s method, for promoting depolymerization of lignin in Barta’s method, for completely dissolving Barta’s lignin in Barta’s system, and for further purifying Barta’s oligomer in Barta’s method, as explained in the rejection of claims 1 and 2 that is set forth in this Office action. Furthermore, one of ordinary skill in the art would have been motivated to modify these process conditions because it would have been beneficial for making Barta’s method more effective at depolymerizing lignin into an oligomer and purifying the oligomer.
In response to the applicant’s argument that Barta and Van Es do not teach or suggest the functionality or benefits of the lignin oligomer being obtained as a precipitate, and that as such, a person having ordinary skill in the art could not have arrived at the present claims without the use of impermissible hindsight (p. 7), it must be recognized that any judgment on obviousness is in a sense necessarily a reconstruction based upon hindsight reasoning. But so long as it takes into account only knowledge which was within the level of ordinary skill at the time the claimed invention was made, and does not include knowledge gleaned only from the applicant's disclosure, such a reconstruction is proper. See In re McLaughlin, 443 F.2d 1392, 170 USPQ 209 (CCPA 1971). The Office’s judgment on obviousness takes into account only the teachings of Barta and Van Es and the knowledge of one of ordinary skill in the art before the effective filing date of the claimed invention. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to use a step of purifying Barta’s oligomer by precipitation to modify Barta’s method. The proposed modification would read on the process thereby obtaining a precipitated lignin oligomer as claimed in claim 1, and the process further comprising the step of: c) obtaining precipitated lignin oligomer as claimed in claim 2. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for further purifying Barta’s oligomer in Barta’s method because Barta teaches that the method optionally further includes the step of purifying the oligomer using a method of purification (p. 7, l. 6-7), that the method optionally further includes the step of purifying the monomer using a method of purification (p. 6, l. 4-6), and that if necessary, the monomers can be further purified by any method known in the art, such as precipitation (p. 25, l. 8-10).
In response to the applicant’s argument that a showing of unexpected results does not require that every possible embodiment of the claims be demonstrated (p. 7-8), the Office has never required the applicant to demonstrate every possible embodiment of the claims in their showing of unexpected results. The applicant’s arguments of unexpected results are not persuasive because the data to which the applicant refers is the data in Table 5, which had elemental analysis of soluble lignin oligomers obtained under standard conditions using 10 wt% ethanol and 80 wt.-% aqueous NaOH or using 45 wt% ethanol and 45 wt.-% aqueous NaOH (specification p. 15, Table 5). The applicant’s data did not have any comparative examples, and therefore the applicant did not compare the claimed invention with the closest prior art. An affidavit or declaration under 37 CFR 1.132 must compare the claimed subject matter with the closest prior art to be effective to rebut a prima facie case of obviousness (MPEP 716.02)(e)). The applicant’s arguments of unexpected results are not persuasive also because the applicant did not establish that the results are in fact unexpected and significant because the applicant did not show that the results are in fact different from the results one of ordinary skill in the art would have expected before the effective filing date of the claimed invention. The evidence relied upon should establish "that the differences in results are in fact unexpected and unobvious and of both statistical and practical significance (MPEP 716.02(b)(I))." Since the applicant did not refer to any comparative examples, the applicant did not show that the results are in fact different from the results one of ordinary skill in the art would have expected. Although the applicant referred to the results as “unexpected results” and “surprising results”, this does not show that the results are in fact unexpected. Although the applicant, in their arguments filed on 09/17/2025, referred to paragraph [0023] of the published application, paragraph [0023] states that “surprisingly, in the range of 5 to 45 wt.-%, preferably 10 to 20 wt.-%, primary alcohol based on the total weight of the aqueous mixture, precipitation of desired lignin occurs without additional formation of char-type lignin residues”. The applicant did not refer to any comparative examples and therefore did not show that these results are in fact different from the results one of ordinary skill in the art would have expected. Although the applicant, in their arguments filed on 09/17/2025, referred to paragraph [0025] of the published application, paragraph [0025] states that “surprisingly, the catalyst after use in the process according to the present invention has a prolonged life-time compared to the same catalyst used in processes for lignin depolymerization known in the art” [0025]. The applicant did not refer to any comparative examples and therefore did not show that these results are in fact different from the results one of ordinary skill in the art would have expected. The applicant’s arguments of unexpected results are not persuasive also because the applicant’s data are not commensurate in scope with the claimed invention. Whether the unexpected results are the result of unexpectedly improved results or a property not taught by the prior art, the "objective evidence of nonobviousness must be commensurate in scope with the claims which the evidence is offered to support (MPEP 716.02(d))." In other words, the showing of unexpected results must be reviewed to see if the results occur over the entire claimed range (MPEP 716.02(d)). The results to which the applicant refers is the data in Table 5 of the specification of the instant application, which is an elemental analysis of soluble lignin oligomers obtained under standard conditions using 10 wt% ethanol and 80 wt.-% aqueous NaOH or using 45 wt% ethanol and 45 wt.-% aqueous NaOH (specification p. 15, Table 5). However, claim 1 does not limit the primary alcohol to ethanol, does not limit the amount of primary alcohol to 10 to 45 wt%, and does not require the aqueous mixture to comprise 45 or 80 wt.-% aqueous NaOH. Claim 1 also does not limit the species of the catalyst, and does not limit the amounts of lignin, catalyst, or primary alcohol. The applicant did not show that the results obtained under the conditions shown in Table 5 would be about the same regardless of the species of primary alcohol or catalyst and regardless of the amounts of lignin, catalyst, or primary alcohol. The applicant also did not show a sufficient number of examples that would allow one of ordinary skill in the art to determine a trend in the exemplified data that would allow the artisan to reasonably extend the probative value thereof to any species of primary alcohol or catalyst and any amounts of lignin, catalyst, or primary alcohol. The nonobviousness of a broader claimed range can be supported by evidence based on unexpected results from testing a narrower range if one of ordinary skill in the art would be able to determine a trend in the exemplified data which would allow the artisan to reasonably extend the probative value thereof (MPEP 716.02(d)(I)).
In response to the applicant’s argument that a person having ordinary skill in the art would have recognized that the present application exemplifies the present claims and also discloses relevant preferred embodiments, and that this person therefore would have recognized that the present claims are commensurate in scope with the application (p. 8), the Office has never taken the position that the claims are not commensurate in scope with the application. The Office takes the position that the applicant’s arguments of unexpected results are not persuasive because the applicant’s data are not commensurate in scope with the claimed invention. Whether the unexpected results are the result of unexpectedly improved results or a property not taught by the prior art, the "objective evidence of nonobviousness must be commensurate in scope with the claims which the evidence is offered to support (MPEP 716.02(d))." In other words, the showing of unexpected results must be reviewed to see if the results occur over the entire claimed range (MPEP 716.02(d)). The applicant’s results are not commensurate in scope with the claimed invention because the results to which the applicant refers is the data in Table 5 of the specification of the instant application, which is an elemental analysis of soluble lignin oligomers obtained under standard conditions using 10 wt% ethanol and 80 wt.-% aqueous NaOH or using 45 wt% ethanol and 45 wt.-% aqueous NaOH (specification p. 15, Table 5). However, claim 1 does not limit the primary alcohol to ethanol, does not limit the amount of primary alcohol to 10 to 45 wt%, and does not require the aqueous mixture to comprise 45 or 80 wt.-% aqueous NaOH. Claim 1 also does not limit the species of the catalyst, and does not limit the amounts of lignin, catalyst, or primary alcohol. The applicant did not show that the results obtained under the conditions shown in Table 5 would be about the same regardless of the species of primary alcohol or catalyst and regardless of the amounts of lignin, catalyst, or primary alcohol. The applicant also did not show a sufficient number of examples that would allow one of ordinary skill in the art to determine a trend in the exemplified data that would allow the artisan to reasonably extend the probative value thereof to any species of primary alcohol or catalyst and any amounts of lignin, catalyst, or primary alcohol. The nonobviousness of a broader claimed range can be supported by evidence based on unexpected results from testing a narrower range if one of ordinary skill in the art would be able to determine a trend in the exemplified data which would allow the artisan to reasonably extend the probative value thereof (MPEP 716.02(d)(I)). The applicant’s results are therefore not commensurate in scope with the claimed invention.
In response to the applicant’s argument that it is not necessary to amend claim 1 to include all the features reference by the Office (p. 8-9), the Office has never take the position that it is necessary for the applicant to amend claim 1 to include certain features or critical features. The Office takes the position that the applicant’s arguments of unexpected results are not persuasive also because the applicant’s data are not commensurate in scope with the claimed invention. Whether the unexpected results are the result of unexpectedly improved results or a property not taught by the prior art, the "objective evidence of nonobviousness must be commensurate in scope with the claims which the evidence is offered to support (MPEP 716.02(d))." In other words, the showing of unexpected results must be reviewed to see if the results occur over the entire claimed range (MPEP 716.02(d)). The results to which the applicant refers is the data in Table 5 of the specification of the instant application, which is an elemental analysis of soluble lignin oligomers obtained under standard conditions using 10 wt% ethanol and 80 wt.-% aqueous NaOH or using 45 wt% ethanol and 45 wt.-% aqueous NaOH (specification p. 15, Table 5). However, claim 1 does not limit the primary alcohol to ethanol, does not limit the amount of primary alcohol to 10 to 45 wt%, and does not require the aqueous mixture to comprise 45 or 80 wt.-% aqueous NaOH. Claim 1 also does not limit the species of the catalyst, and does not limit the amounts of lignin, catalyst, or primary alcohol. The applicant did not show that the results obtained under the conditions shown in Table 5 would be about the same regardless of the species of primary alcohol or catalyst and regardless of the amounts of lignin, catalyst, or primary alcohol. The applicant also did not show a sufficient number of examples that would allow one of ordinary skill in the art to determine a trend in the exemplified data that would allow the artisan to reasonably extend the probative value thereof to any species of primary alcohol or catalyst and any amounts of lignin, catalyst, or primary alcohol. The nonobviousness of a broader claimed range can be supported by evidence based on unexpected results from testing a narrower range if one of ordinary skill in the art would be able to determine a trend in the exemplified data which would allow the artisan to reasonably extend the probative value thereof (MPEP 716.02(d)(I)).
In response to the applicant’s argument that the surprising results of the application are sufficient to rebut a prima facie case of obviousness (p. 9), the applicant’s arguments of unexpected results are not persuasive because the data to which the applicant refers is the data in Table 5, which had elemental analysis of soluble lignin oligomers obtained under standard conditions using 10 wt% ethanol and 80 wt.-% aqueous NaOH or using 45 wt% ethanol and 45 wt.-% aqueous NaOH (specification p. 15, Table 5). The applicant’s data did not have any comparative examples, and therefore the applicant did not compare the claimed invention with the closest prior art. An affidavit or declaration under 37 CFR 1.132 must compare the claimed subject matter with the closest prior art to be effective to rebut a prima facie case of obviousness (MPEP 716.02)(e)). The applicant’s arguments of unexpected results are not persuasive also because the applicant did not establish that the results are in fact unexpected and significant because the applicant did not show that the results are in fact different from the results one of ordinary skill in the art would have expected before the effective filing date of the claimed invention. The evidence relied upon should establish "that the differences in results are in fact unexpected and unobvious and of both statistical and practical significance (MPEP 716.02(b)(I))." Since the applicant did not refer to any comparative examples, the applicant did not show that the results are in fact different from the results one of ordinary skill in the art would have expected. Although the applicant referred to the results as “unexpected results” and “surprising results”, this does not show that the results are in fact unexpected. Although the applicant, in their arguments filed on 09/17/2025, referred to paragraph [0023] of the published application, paragraph [0023] states that “surprisingly, in the range of 5 to 45 wt.-%, preferably 10 to 20 wt.-%, primary alcohol based on the total weight of the aqueous mixture, precipitation of desired lignin occurs without additional formation of char-type lignin residues”. The applicant did not refer to any comparative examples and therefore did not show that these results are in fact different from the results one of ordinary skill in the art would have expected. Although the applicant, in their arguments filed on 09/17/2025, referred to paragraph [0025] of the published application, paragraph [0025] states that “surprisingly, the catalyst after use in the process according to the present invention has a prolonged life-time compared to the same catalyst used in processes for lignin depolymerization known in the art” [0025]. The applicant did not refer to any comparative examples and therefore did not show that these results are in fact different from the results one of ordinary skill in the art would have expected. The applicant’s arguments of unexpected results are not persuasive also because the applicant’s data are not commensurate in scope with the claimed invention. Whether the unexpected results are the result of unexpectedly improved results or a property not taught by the prior art, the "objective evidence of nonobviousness must be commensurate in scope with the claims which the evidence is offered to support (MPEP 716.02(d))." In other words, the showing of unexpected results must be reviewed to see if the results occur over the entire claimed range (MPEP 716.02(d)). The results to which the applicant refers is the data in Table 5 of the specification of the instant application, which is an elemental analysis of soluble lignin oligomers obtained under standard conditions using 10 wt% ethanol and 80 wt.-% aqueous NaOH or using 45 wt% ethanol and 45 wt.-% aqueous NaOH (specification p. 15, Table 5). However, claim 1 does not limit the primary alcohol to ethanol, does not limit the amount of primary alcohol to 10 to 45 wt%, and does not require the aqueous mixture to comprise 45 or 80 wt.-% aqueous NaOH. Claim 1 also does not limit the species of the catalyst, and does not limit the amounts of lignin, catalyst, or primary alcohol. The applicant did not show that the results obtained under the conditions shown in Table 5 would be about the same regardless of the species of primary alcohol or catalyst and regardless of the amounts of lignin, catalyst, or primary alcohol. The applicant also did not show a sufficient number of examples that would allow one of ordinary skill in the art to determine a trend in the exemplified data that would allow the artisan to reasonably extend the probative value thereof to any species of primary alcohol or catalyst and any amounts of lignin, catalyst, or primary alcohol. The nonobviousness of a broader claimed range can be supported by evidence based on unexpected results from testing a narrower range if one of ordinary skill in the art would be able to determine a trend in the exemplified data which would allow the artisan to reasonably extend the probative value thereof (MPEP 716.02(d)(I)).
In response to the applicant’s argument that Massey-Brooker, Qiu, and Cheng do not cure the deficiencies of Barta and Van Es at least because Massey-Brooker, Qiu, and Cheng do not teach or suggest all the elements of the present claims and has not been cited for such (p. 10-11), the combination of Barta in view of Van Es does not have the deficiencies argued by the applicant, as explained above in the Office’s response to the applicant’s arguments against the combination of Barta in view of Van Es.
In response to the applicant’s argument that Applicant respectfully requests consideration of rejoinder of withdrawn claims 16-19 and 21 should claim 1 be found to be allowable (p. 11), claim 1 is not allowable and therefore the Office has not rejoined withdrawn claims 16-19 and 21.
Correspondence
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/DAVID T KARST/Primary Examiner, Art Unit 1767