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 of Species 1, Species A, and Species III in the reply filed on August 5, 2026 is acknowledged. Because applicant did not distinctly and specifically point out the supposed errors in the restriction requirement, the election has been treated as an election without traverse (MPEP § 818.01(a)).
Claims 3, 12, 14, and 15 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected species, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on August 5, 2026.
Claims 1, 2, 4-11, 13, and 16 read on the elected species and are examined on the merits.
Claim Objections
Claim 6 is objected to because of the following informalities:
Regarding claim 6, in line 3, articles need to be inserted before each of the named functional groups so that the claim reads, “an OH group, a COOH group, a NH2 group.”
Appropriate correction is required.
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 2, 5, 7, and 13 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.
Regarding claim 2, this claim recites “the coupling reagent (II)” in line 1. However, the coupling agent is of formula (I). It is unclear if claim 2 is referring to the coupling agent or the structure of formula (II). For the purpose of further examination, this limitation will be interpreted as “the coupling reagent (I).”
Regarding claim 5, claim 5 recites the limitation "the lignin" in line 1. There is insufficient antecedent basis for this limitation in the claim. For the purpose of further examination, this limitation will be interpreted as referring to the lignin-based material in line 2 of claim 1.
Regarding claim 7, in line 1, the claim recites “the step of reacting.” However, since claim 7 depends from claim 6 which depends from claim 1, there are two reacting steps in the method – (1) reacting a lignin-based material having one or more OH group with a coupling reagent having a formula (I); and (2) reacting the first lignin-based material comprising one or more moieties of formula (II) with a first compound comprising at least one of an OH group, a COOH group, a NH₂ group, or a combination thereof. It is unclear to which reacting step claim 7 refers. For the purpose of further examination, the reacting step of claim 7 will be interpreted as referring to the second reacting step of claim 6.
Regarding claim 13, claim 13 recites the limitation "the second compound" in line 1. There is insufficient antecedent basis for this limitation in the claim. For the purpose of further examination, this claim will be interpreted to depend from claim 7 which does introduce a second compound.
Claim Rejections - 35 USC § 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claim 16 is rejected under 35 U.S.C. 102(a)(1) as being anticipated by Chung (WO 2021/142079).
Regarding claim 16, Chung teaches a biodegradable polyester polymer comprising a lignin-containing segment and a vegetable-oil based segment, wherein the lignin-containing segment and the vegetable-oil based segment are linked through ester linkages, and wherein the biodegradable polyester polymer has a linear or a double networked molecular structure (¶6) (a polyester). The lignin-containing segment comprises a first repeating unit derived from a functionalized lignin monomer comprising carboxylic functional groups (¶115), and the carboxylic functional groups can come from a residue of sebacic acid or succinic acid (¶66). The polyester is produced by functionalizing a lignin having terminal hydroxyl groups to form a functionalized lignin segment comprising terminal carboxylic functional groups, reacting a vegetable-oil based lactone to form a dialcohol-containing segment, and polymerizing the functionalized lignin segment comprising terminal carboxylic functional groups with the formed dialcohol-containing segment to form the biodegradable polyester polymer (¶46, 100).
This claim is a product-by-process claim recited a polyester formed by the method of claim 1. Even though product-by-process claims are limited by and defined by the process, determination of patentability is based on the product itself. The patentability of a product does not depend on its method of production. If the product in the product-by-process claim is the same as or obvious from a product of the prior art, the claim is unpatentable even though the prior product was made by a different process.” In re Thorpe, 777 F.2d 695, 698, 227 USPQ 964, 966 (Fed. Cir. 1985). In this case, there is no evidence on the record that the method of production produces a composition that is not the same as or obvious from the product of the prior art.
Claim Rejections - 35 USC § 103
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
Claims 1, 2, 4-8, and 11 are rejected under 35 U.S.C. 103 as being unpatentable over Okabe et al. (US 2012/0190812) in view of Hodgdon et al. (US 2019/0309238) and Costantino et al. (WO 2003/080678).
Regarding claims 1 and 2, Okabe et al. teaches a method for producing a polycarbonate resin comprising the steps of converting part or all of hydroxyl groups of a plant-based material having a plurality of hydroxyl groups into carbonate groups and polymerizing the plant-based material (¶24; claim 10), wherein the plant-based material is lignin (¶34; claim 2) (a lignin-based material having one or more OH groups). In Example 1, 20 g (0.025 mol, hydroxyl group equivalent 120 g/eq) of lignin is stirred and dissolved in 10 ml of pyridine and 100 ml of dry dichloromethane, phosgene gas is introduced into the resulting reaction mixture at a flow rate of 100 ml/min while the mixture is held at 5 °C to 10 °C with ice-cooling, and the reaction is stopped one hour into the gas introduction to yield a lignin-based polycarbonate resin (¶46). Okabe et al. teaches that the hydroxyl groups of the lignin react with the phosgene to form carbonic ester bonds, and that these bonds link the lignin molecules to each other to form a polymer (¶47), and confirms the resulting carbonic ester by an infrared absorption at 1770 cm-1 assigned to the C=O stretching vibration of a carbonic ester (¶48).
Okabe et al. does not teach that the reagent reacted with the hydroxyl groups of the lignin is a coupling reagent having formula (I), that is, a compound in which two imidazol-1-yl rings are joined to one another through a central carbonyl group, nor that the product of that reaction is a first lignin-based material comprising one or more moieties of formula (II), in which the lignin oxygen is bonded to a carbonyl group bearing an imidazol-1-yl group.
However, Hodgdon et al. teaches a water-soluble polyurethane derived from polyethylene glycol, 1,1'-carbonyldiimidazole, and a polyamine (¶4). In a typical synthesis, 2,000 g/mol poly(ethylene glycol) (10 g, 0.005 mol, Mn ~2,000 g/mol) and 1,1'-carbonyldiimidazole (4.05 g, 0.025 mol) are introduced into a round-bottomed flask, the monomers are dissolved in chloroform (50 mL), and the solution is purged with nitrogen gas; the product is then washed three times with deionized water and once with brine water to remove the imidazole side product, and the purified product (5.0 g, 0.0022 mol) is subsequently charged with 2,2'-(ethylenedioxy)bis(ethylamine) (6.6 g, 0.044 mol) in chloroform (45 mL) (¶89). 1,1'-Carbonyldiimidazole is a compound in which two imidazol-1-yl rings are joined through a central carbonyl group, and therefore corresponds to the coupling reagent of formula (I) wherein Rl is -C(O)- and R2, R3, and R4 are each hydrogen, which is the species recited in claim 2. Because one imidazol-1-yl group departs as the imidazole side product that Hodgdon et al. washes away, the purified intermediate that Hodgdon et al. isolates before adding the amine is a material in which the polyol oxygen is bonded to a carbonyl group that still bears the second imidazol-1-yl group, which corresponds to the moiety of formula (II).
Costantino et al. confirms the identity of that intermediate, teaching that a hydroxyl-bearing material is first activated through at least one of its hydroxyl groups using 1,1'-carbonyldiimidazole in dimethyl sulfoxide solvent and that the resulting imidazole carbamate intermediate is trapped by an amine to give the modified product (Page 10, lines 16-19), and teaching elsewhere that conjugation may involve reaction of a hydroxyl group with 1,1’-carbonyldiimidazole to form a 1,1’-carbonyldiimidazole carbamate intermediate and coupling of the 1,1’-carbonyldiimidazole carbamate intermediate with an amino group (Page 14, lines 28-31). Costantino et al. teaches that bifunctional reagents for this purpose include 1,1'-carbonyldiimidazole, carbonyl di-1,2,4-triazole, carbonyl di-1,2,3-benzotriazole, diphenylcarbonate, cyanogen bromide, phosgene, or triphosgene (Page 9, lines 16-19), and thus places 1,1’-carbonyldiimidazole and the phosgene of Okabe et al. in the same class of reagents performing the same function.
Okabe et al. and Hodgdon et al. are analogous art because they are from the same field of endeavor as that of the instant invention, namely that of converting the hydroxyl groups of a hydroxyl-bearing material into an activated carbonyl species and coupling that species to a second compound to form a polymer. Costantino et al. is analogous art because it is reasonably pertinent to the particular problem with which the inventor was concerned, namely the selection of a carbonyl-transfer reagent for activating the hydroxyl groups of a hydroxyl-bearing material prior to coupling. At the time of the filing of the instant invention, a person of ordinary skill in the art would have found it obvious to substitute the 1,l'-carbonyldiimidazole, as taught by Hodgdon et al. and Costantino et al., for the phosgene used to convert the hydroxyl groups of the lignin into carbonate groups, in the method as taught by Okabe et al., and would have been motivated to do so because Costantino et al. teaches that a preferred bifunctional reagent is 1,1’-carbonyldiimidazole, that 1,1’-carbonyldiimidazole has the advantage of being a milder reagent than, for example, phosgene or cyanogen bromide, that coupling reactions using 1,1’-carbonyldiimidazole do not generate hydrohalic acid gases such as HCl or HBr, and that the generation of HCl or HBr gas is undesirable because these gases require scrubbing of the reaction chamber outlet to avoid their escape into the atmosphere (Page 9, lines 20-25). This is a substitution of one known carbonyl-transfer reagent for another to perform the same function, and would have yielded the predictable result of a lignin bearing an activated carbonyl group at its former hydroxyl positions, that is, the first lignin-based material comprising one or more moieties of formula (II).
Regarding claim 4, Okabe et al. does not teach that the step of reacting is performed at a temperature from about 20 °C to about 35 °C. However, Hodgdon et al. teaches that the reaction between the poly(ethylene glycol) and the 1,l'-carbonyldiimidazole proceeded at 25 °C for 30 min, and that the subsequent reaction of the purified product with the amine was allowed to proceed at 25 °C for 2 h under nitrogen (¶89). At the time of the filing of the instant invention, a person of ordinary skill in the art would have found it obvious to carry out the reaction between the lignin and the 1,1'-carbonyldiimidazole at 25 °C, as taught by Hodgdon et al., in the method, as taught by Okabe et al., and would have been motivated to do so because Hodgdon et al. teaches that this is the temperature at which 1,1'-carbonyldiimidazole reacts with the hydroxyl groups of a polymeric polyol to completion in 30 minutes (¶89), and because Costantino et al. teaches that 1,1’-carbonyldiimidazole is a milder reagent than phosgene (Page 9, lines 20-21), such that the ice-cooling to 5 °C to 10 °C required by the phosgene process of Okabe et al. is no longer necessary.
Regarding claim 5, Okabe et al. teaches that the plant-based material used as the raw material has a weight-average molecular weight of from 300 to 8000 (¶35).
Regarding claims 6-8 and 11, Okabe et al. teaches in Example 6 that a polycarbonate resin copolymer is prepared by the procedure of Example 1 except that 160.0 g (0.2 mol) of the lignin used in Example 1 and 11.4 g (0.05 mol) of 2,2-bis(4-hydroxyphenyl)propane, i.e., bisphenol-A, are mixed and dissolved in 400 ml of dry dichloromethane (¶78), and teaches the same copolymerization in Example 7 using 40.0 g (0.05 mol) of lignin and 46.0 g (0.2 mol) of bisphenol-A (¶79). Bisphenol-A is a compound comprising two OH groups (corresponds to a first compound), is a functional chemical compound1, and is a bisphenol. Okabe et al. further teaches that the hydroxyl groups of the plant-based material and the hydroxyl groups of the bifunctional hydroxyl-containing petroleum-based material (the bisphenol-A) are converted into carbonate groups and linked to each other to form the copolymer (¶19) (a second compound comprising a polycarbonate, such that the first compound is covalently bound to the first lignin-based material).
Claims 9, 10, and 13 are rejected under 35 U.S.C. 103 as being unpatentable over Okabe et al. (US 2012/0190812) in view of Hodgdon et al. (US 2019/0309238) and Costantino et al. (WO 2003/080678) as applied to claim 6 above, and further in view of Chung (WO 2021/142079).
Regarding claims 9, 10, and 13, Okabe et al., Hodgdon et al., and Costantino et al. teach the method of claim 6 as set forth above. Okabe et al., Hodgdon et al., and Costantino et al. do not teach that the first compound is an oligomer or a polymer, that the first compound comprises a polyester, or that the second compound, i.e., the resulting compound, is biodegradable. However, Chung teaches a method comprising functionalizing a lignin having terminal hydroxyl groups to form a functionalized lignin segment comprising terminal carboxylic functional groups, reacting a vegetable-oil based lactone to form a dialcohol-containing segment, and polymerizing the functionalized lignin segment with the formed dialcohol-containing segment to form a biodegradable polyester polymer, wherein the formed biodegradable polyester polymer comprises a lignin-containing segment linked to a vegetable-oil based segment through ester linkages (¶46, 100). Chung teaches that the dialcohol-containing segment can be a dialcohol-containing monomer, a dialcohol-containing polymer, or a combination thereof (¶96). Chung further teaches that the vegetable-oil based lactone can comprise ethylene brassylate, a 17-membered ring lactone, and that where there is no requirement for a dialcohol segment, the vegetable-oil based segment can be formed by a direct ring-opening polymerization of ethylene brassylate to form a polyethylene brassylate (¶87, 89), which is an aliphatic polyester. Additionally, Chung teaches that the disclosed biodegradable polyester polymer can degrade after 12 months to within about 14 months when exposed to one or more of saltwater, UV irradiation, hydraulic forces, a mechanical loading, a temperature change, or microorganisms (¶137), and defines the term "biodegradable" as referring to a material capable of being decomposed by bacteria or other living microorganisms (¶42).
Okabe et al. and Chung are analogous art because they are from the same field of endeavor as that of the instant invention, namely that of lignin-based polymers formed by reacting the hydroxyl groups of a lignin with a second compound. At the time of the filing of the instant invention, a person of ordinary skill in the art would have found it obvious to use a dialcohol-containing polymer, and specifically the polyethylene brassylate polyester, as taught by Chung, as the first polymer in the method, as taught by Okabe et al. and modified by Hodgdon et al. and Costantino et al., and would have been motivated to do so in order to obtain a biodegradable polymer. Chung teaches that there is a need for plastic materials made from renewable sources that can easily degrade within a desirable time without leaching harmful materials (¶5).
Correspondence
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ANGELA C SCOTT whose telephone number is (571)270-3303. The examiner can normally be reached Monday-Friday, 8:30-5:00, EST.
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/ANGELA C SCOTT/Primary Examiner, Art Unit 1767
1 The instant specification does not define “functional chemical compound” and therefore the term is given its broadest reasonable interpretation. Any compound that has a functional group will meet this limitation.
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