Prosecution Insights
Last updated: April 19, 2026
Application No. 18/096,849

METHODS OF PLASTIC RECYCLING USING HIGHLY EFFICIENT ORGANOCATALYSTS

Non-Final OA §102§103§112§DP
Filed
Jan 13, 2023
Examiner
BONAPARTE, AMY C
Art Unit
1692
Tech Center
1600 — Biotechnology & Organic Chemistry
Assignee
UT-BATTELLE, LLC
OA Round
1 (Non-Final)
80%
Grant Probability
Favorable
1-2
OA Rounds
2y 2m
To Grant
99%
With Interview

Examiner Intelligence

Grants 80% — above average
80%
Career Allow Rate
584 granted / 734 resolved
+19.6% vs TC avg
Strong +24% interview lift
Without
With
+23.8%
Interview Lift
resolved cases with interview
Typical timeline
2y 2m
Avg Prosecution
40 currently pending
Career history
774
Total Applications
across all art units

Statute-Specific Performance

§101
1.6%
-38.4% vs TC avg
§103
33.3%
-6.7% vs TC avg
§102
15.7%
-24.3% vs TC avg
§112
32.8%
-7.2% vs TC avg
Black line = Tech Center average estimate • Based on career data from 734 resolved cases

Office Action

§102 §103 §112 §DP
DETAILED ACTION Notice of Pre-AIA or AIA Status The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA. Claim Status Claims 1-25 were filed on 1/13/2023 and are currently pending. Priority The instant application was filed 1/13/2023 and claims the benefit of priority to: See filing receipt dated 4/4/2023. Specification /Drawings The drawings are objected to because they are blurry and difficult to read. Corrected drawing sheets in compliance with 37 CFR 1.121(d) are required in reply to the Office action to avoid abandonment of the application. Any amended replacement drawing sheet should include all of the figures appearing on the immediate prior version of the sheet, even if only one figure is being amended. The figure or figure number of an amended drawing should not be labeled as “amended.” If a drawing figure is to be canceled, the appropriate figure must be removed from the replacement sheet, and where necessary, the remaining figures must be renumbered and appropriate changes made to the brief description of the several views of the drawings for consistency. Additional replacement sheets may be necessary to show the renumbering of the remaining figures. Each drawing sheet submitted after the filing date of an application must be labeled in the top margin as either “Replacement Sheet” or “New Sheet” pursuant to 37 CFR 1.121(d). If the changes are not accepted by the examiner, the applicant will be notified and informed of any required corrective action in the next Office action. The objection to the drawings will not be held in abeyance. The disclosure is objected to because of the following informalities: The Tables in [0072-0073] on p. 25-27 of the specification as filed are objected to because they contain misspellings. Every instance of “fluoro” in the Table in [0072] is misspelled as “fluro”. In the Table in [0073] the base name for “DBU” should be in black and not greyscale. Further, the final base in the table, TMG, is given the name : “tetrametylguanidine”. This name is both misspelled (tetramet h ylguanidine) and incorrectly describes the structure shown. The structure, TMG, is shown to correspond to a trimethylguanidine, as only three methyl groups are present and not four. Appropriate correction is required. Claim Rejections - 35 USC § 112(b) 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 appl icant regards as his invention. Claim 9 is 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. There is a lack of antecedent basis for the structure (1h) of claim 9 with respect to structure (1) in claim 1 : vs, . As required in claim 1 , structure (1) requires at least two “N” atoms, wherein X may be a C, C R a , or N group. Further, structure (1) shows that variable X is attached to variables R 3 and R 4 and that a N atom is attached to variables R 5 and R 6 . Thus, mapping structure (1h) back to structure (1) would require the group “NR 4 ” to correspond to X-R 4 , wherein R 2 and R 3 are joined to form a six membered ring and R 5 and R 6 to be attached to a CR a group, wherein R a is H and R 5 and R 1 are joined to form a seven membered ring. R 5 and R 6 are required to be attached to a N atom, therefore, the structure (1h) lacks antecedent basis to structure (1) of claim 1 . This rejection would be overcome by replacing the variable “R 4 ” in structure (1h) with the variable “R 6 ”. Claim Rejections - 35 USC § 102 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 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. (a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention. Claim(s) 1-4, 9, 11, 12, 17, 19, 20, and 22-25 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Demarteau (“Aminolytic upcycling of poly(ethylene terephthalate) wastes using a thermally-stable organocatalyst”, Polymer Chemistry, 2020, p. 4875, of record in the IDS filed 5/10/2023). Demarteau teaches reacting PET (polyethylene terephthalate, a polyester and condensation polymer- claims 17 , 19, and 20 ) waste ; with a catalyst (DBU:BA) comprising an organic nitrogen containing base (DBU, 1,2-diazabicyclo[5.4.0]undec-7-ene, not pictured below) and a carboxylic acid (BA, benzoic acid) in an equimolar (1:1) ratio ( claims 22-25 ) ; in the presence of a protic molecule (ethanolamine, EA), which is an amine and alcohol; at an elevated temperature (180°C) effective for inducing aminolysis of the condensation polymer (PET) to produce a monomeric useful breakdown product (BHETA, bis(2-hydroxyethyl)terephthalamide) which is capable of being polymerized: . See Figure 1 on p. 4876 and discussion thereof on p. 4867-4877, wherein “DBA:BA” is defined in the last paragraph of the first col. of p. 4876 and “BHETA” is defined at the top of the first col. on p. 4876. BHETA corresponds to the product in Fig. 1(A) above. Also see Table 2 on p. 4880 and discussion thereof, regarding the polymerization of BHETA, also using the DBA:BA catalyst. As evidenced by [0048] on p. 16 of the specification as filed, DBU is an organic nitrogen-containing base of the following structure: . Thus, DBU corresponds to a compound of structure (1) in claim 1 , wherein X is CR a , R a is H; R 4 is H; R 3 and R 2 are interconnected to form a seven-membered ring, wherein the combination of R 3 and R 2 is an alkylene group having five carbon atoms; R 6 is an electron pair and a double bond is present; and R 5 and R 1 are interconnected to form a six-membered ring, wherein the combination of R 5 and R 1 is an alkylene group having three carbon atoms. Thus, DBU also anticipates the base in claims 2-4 and 9 , wherein the R variables are as defined above and wherein variable r is 1 and variable s is 2. As evidenced by [0072] on p. 26 of the specification as filed benzoic acid is of the following structure: . Benzoic acid corresponds to a compound of structure (2) in claims 11-12 wherein R is a 6 membered unsubstituted hydrocarbon group and R b is H. Also see MPEP 2131.02. Claim(s) 1-4, 9, 11, 12, 15- 17, and 19 - 25 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Alabdulrahman ( US 2012/0223270 , published on 9/6/2012). Alabdulrahman teaches reacting PET (polyethylene terephthalate, a polyester and condensation polymer- claims 17 , 19, and 20 ) post-consumer waste; with i) a catalyst (DBU - BA) comprising an organic nitrogen containing base (DBU, 1,2-diazabicyclo[5.4.0]undec-7-ene) and a carboxylic acid (BA, benzoic acid) or ii) a catalyst (DBU-TA) comprising DBU and terephthalic acid (TA) as the carboxylic acid in the presence of a protic molecule ( ethylene glycol , E G ), which is a diol ( claims 15-16 ) ; at an elevated temperature (1 9 0°C) effective for inducing glycolysis (alcoholysis with EG) of the condensation polymer (PET) to produce a monomeric useful breakdown product (BHET, bis(2- hydroxyethyl) terephthalate ) , claim 21 ) which is capable of being polymerized: . See [0079-0084, 0092-0094, 0101, 0103, 0105, 0106, 0135-0137, and 0140-0143]. Thus, DBU corresponds to a compound of structure (1) in claim 1 , wherein X is CR a , R a is H; R 4 is H; R 3 and R 2 are interconnected to form a seven-membered ring, wherein the combination of R 3 and R 2 is an alkylene group having five carbon atoms; R 6 is an electron pair and a double bond is present; and R 5 and R 1 are interconnected to form a six-membered ring, wherein the combination of R 5 and R 1 is an alkylene group having three carbon atoms. Thus, DBU also anticipates the base in claims 2-4 and 9 , wherein the R variables are as defined above and wherein variable r is 1 and variable s is 2. As evidenced by [0072] on p. 26 of the specification as filed , and Fig. 8 of Alabdulrahman , benzoic acid is of the following structure: . Benzoic acid corresponds to a compound of structure (2) in claims 11-12 wherein R is a 6 membered unsubstituted hydrocarbon (phenyl) group and R b is H. Terephthalic acid corresponds to the diacid of BHET, which corresponds to a compound of structure (2) in claims 11-12 wherein R is a six-membered hydrocarbon (phenyl) group substituted by another carboxylic acid group. Regarding claims 22-25 , in Table 4 i n [0135] , Alabdulrahman teaches DBU:BA molar ratios of 1:1 (equimolar), 1:2 (0.5:1), and 1:8 (0.125:1). Also see MPEP 2131.02. 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. The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows: 1. Determining the scope and contents of the prior art. 2. Ascertaining the differences between the prior art and the claims at issue. 3. Resolving the level of ordinary skill in the pertinent art. 4. Considering objective evidence present in the application indicating obviousness or nonobviousness. This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention. Claim(s) 1-9, 11, 12, 15-17, and 19-25 is/are rejected under 35 U.S.C. 103 as being unpatentable over Alabdulrahman ( US 2012/0223270 , published on 9/6/2012 ) . The Applicant claims the genus process of claim 1 , wherein the organic nitrogen-containing base is other than DBU, specifically one of those in claims 5-8. The Applicant also claims a genus wherein the carboxylic acid is not limited to benzoic acid and terephthalic acid . The teachings of Alabdulrahman regarding the anticipatory reaction of PET to BHET in the presence of EG using DBU-BA or DBU-TA as a catalyst were discussed in detail above and are incorporated herein. However, Alabdulrahman also teaches other embodiments which render the instantly claimed process prima facie obvious. Alabdulrahman is more broadly directed toward the depolymerization of terephthalate polyesters in the presence of a glycol comprising 2 to 5 carbon atoms and an amidine organocatalyst, heating the reaction mixture at a temperature of about 120°C or more to depolymerize the terephthalate polyester, thereby forming a terephthalate reaction product comprising a monomeric dihydroxy terephthalate diester. See abstract and claims. Alabdulrahman teaches the amidine (organic-nitrogen containing base) organocatalysts for the depolymerization with glycols comprising 2 to 5 carbon atoms are of the following formula (2): , wherein the amidine functional group can reside in an acyclic or cyclic structure. Preferably the amidine is DBU (addressed in detail above) or DBN (1,4-diazabicyclo(4.3.0)non-5-ene. See [0041-0046]. As evidenced by [0073] on p. 27 of the specification as filed, DBN is a compound of the following structure: . DBN corresponds to an organic nitrogen-containing base of formula (I) of claim s 1 -4 and formula (1g) in claim 8 , wherein X is CR a , R a is H, R 4 is H, R 3 and R 2 are interconnected to form a five-membered ring, R 1 and R 5 are connected to form a six-membered ring, and R 6 is an electron pair, wherein one of the double bonds is present , and r is 1 and s is 0 . Alabdulrahman also teaches an embodiment wherein when the glycols (diols) are substituted for mono-alcohols that the preferred organic nitrogen containing base is TBD (triazabicyclo[4.40]dec-4-ene). See [0046-0047]. As evidenced by [0073] on p. 27 of the specification as filed, TBD is of the following formula: . TBD corresponds to an organic nitrogen-containing base of formula (I) of claim s 1 -7 wherein X is N, R 4 is H, R 3 and R 2 are interconnected to form a six-membered ring, R 1 and R 5 are connected to form a six-membered ring, and R 6 is an electron pair, wherein one of the double bonds is present, and r and s are 1 when present. Also see [0133-0134]. Alabdulrahman further teaches that the amidine organocatalyst can be present in the form of the acid-base salt, wherein the acid includes carboxylic acids. Benzoic acid and terephthalic acid are preferred. Alabdulrahman teaches that when the catalysts are in the salt form that they have greater air and thermal stability at the elevated depolymerization temperature compared to the free base organocatalyst. See [0048-0051] and [0137]. Though Alabdulrahman does not explicitly teach that TBD, a guanidine catalyst, can also be used as a salt, a person of ordinary skill would have been motivated to prepare the salt of TBD with a reasonable expectation of success of obtaining a reactive but more thermally and air stable catalyst. See last example in Table 5 in [0137], which shows that the free base of TBD is comparable to that of DBU. Alabdulrahman further teaches that the terephthalate polyesters are not limited to PET and can also include poly(butylene terephthalate) (PBT) among others. See [0032]. Alabdulrahman does not explicitly teach other anticipatory examples wherein the base is other than DBU, such as one of those in claims 5-8 . Nor does Alabdulrahman explicitly teach carboxylic acids other than benzoic and terephthalic acid. It would have been prima facie obvious for a person of ordinary skill in the art to arrive at the instantly claimed processes based on the teachings of Alabdulrahman with a reasonable expectation of success before the effective filing date of the claimed invention. A person of ordinary skill would have been motivated to employ other organic nitrogen containing base and carboxylic acid salt catalysts other than those explicitly taught in the examples of Alabdulrahman because Alabdulrahman suggests as much would yield predictable results . Further, Alabdulrahman directs the skilled artisan that when the protic molecule is a glycol, that amidines , such as the DBN and DBU embodiments of claims 1-4 and 8 are superior bases, however, when the protic molecule is a glycol, then guanidines, such as the TBD embodiment of claims 1-7 provides better results. A person of ordinary skill would have been further motivated to use the bases as carboxylate salts because Alabdulrahman teaches that the base form is more stable to the reaction conditions than the free base. Claim(s) 10 is/are rejected under 35 U.S.C. 103 as being unpatentable over Alabdulrahman ( US 2012/0223270 , published on 9/6/2012), as applied to claim(s) 1-9, 11, 12, 15-17, and 19-25 , and further in view of Burdeniuc ( WO 2022/194587A2, published on 9/22/2022, claiming the benefit of priority to PCT/EP2022/055674, filed on 5/7/2022, claiming the benefit of priority to US 63/161693 , published on 1/6/2011). Alabduhlrahman does not explicitly teach the use of a base according to instant claim 10 . Budeniuc is directed toward a method for the recycling of organic polymers, preferably PET, to produce useful chemical intermediates based on their monomeric components. See abstract. Budeniuc claims a process for depolymerizing a difunctional alcohol and at least one organic base catalyst and/or carboxylic acid of the same, wherein the at least one organic base catalyst is an alkyl substituted guanidine of the following structure: . See claims 1-2. The alkyl substituted guanidine corresponds to a compound of formula (1i) in claim 10 wherein instant X is N and instant R 3 , R 4 , R 5 , and R 6 are C 1-3 alkyl and instant R 1 is a C1 -3 alkyl or H. It would have been prima facie obvious to combine the teachings of Alabduhlrahman and Budeniuc to arrive at the instantly claimed process with a reasonable expectation of success before the effective filing date of the claimed invention. A person of ordinary skill would have been motivated to substitute one of the catalysts of Alabduhlrahman for that claimed because Budeniuc teaches that such a catalyst exists and would be expected to provide the desired product with a reasonable expectation of success. Also see MPEP 2143(I)(B). Claim(s) 13 and 14 is/are rejected under 35 U.S.C. 103 as being unpatentable over Alabdulrahman ( US 2012/0223270 , published on 9/6/2012), as applied to claim(s) 1-9, 11, 12, 15-17, and 19-25 , and further in view of Miran (“Physicochemical properties determined by ΔpKa for protic ionic liquids based on an organic super-strong base with various Bronsted acids” Phys. Chem. Chem. Phys. 2012, p. 5178) . Alabduhlrahman generally teaches that carboxylic acids may be used, and preferred embodiments include aromatic acids benzoic acid and terephthalic acid. Alabduhlrahman also teaches that the acid-base activity of the amidine organocatalysts can impart different reactivity to the catalysts. Alabduhlrahman teaches that salt organocatalysts formed with oxo acids such as benzoic acid, one of the best catalysts for the glycolysis reaction, are more likely to exist as an ion pair of a conjugate acid and a conjugate base rather than as dissociated ion pairs or a pair of an acid and a base. See [0046] and [0135-0136]. Alabduhlrahman also teaches that the salt organocatalysts are more thermally and air stable than the corresponding free bases . See [0048-0051] and [0137]. Alabduhlrahman does not explicitly teach the use of a carboxylic acid of claim s 1 3 and 14 . Miran is directed toward the physicochemical properties of protic ionic liquids based on an organic super-strong base, DBU, with various Bronsted acids. See abstract. The acids examined are shown in Fig. 1 on p. 5179: . The acids include acetic acid (CH 3 COOH), trifluoroacetic acid (CF 3 COOH), and formic acid (HCOOH), which are all carboxylic acids of formula (2) of claims 11-14 , wherein R b is H and R is H or a C 1 hydrocarbon, optionally substituted by fluorine, a halogen. Miran teaches that the acids all impart different properties to the resulting DBU catalysts. See abstract and conclusions section. It would have been prima facie obvious to combine the teachings of Alabduhlrahman and Miran to arrive at the instantly claimed process with a reasonable expectation of success before the effective filing date of the instant invention. A person of ordinary skill would have been motivated to employ the acids of claims 13-14 , preferably TFA, as the carboxylic acid component in the catalysts of Alabduhlrahman because Alabduhlrahman teaches that carboxylic “oxo” acids provide some of the best results of the glycolysis reaction and indicates that any carboxylic acid would be an acceptable acid. Further, Miran teaches DBU can also form salts with TFA, acetic acid, and formic acid which will have different physicochemical and thermal properties. Therefore, it would have been prima facie obvious to replace the carboxylic acids exemplified by Alabduhlrahman with other known carboxylic acids, such as those in Miran, in the process of Alabduhlrahman in order to optimize the reaction and extend its utilty. Claim(s) 18 is/are rejected under 35 U.S.C. 103 as being unpatentable over Alabdulrahman ( US 2012/0223270 , published on 9/6/2012), as applied to claim(s) 1-9, 11, 12, 15-17, and 19-25 , and further in view of Jehanno (“Selective Chemical Upcycling of Mixed Plastics Guided by a Thermally Stable Organocatalyst” Angew. Chem. Int. Ed. 2021, p. 6710, of record in the IDS filed on 5/10/2023 ). Alabduhlrahman teaches that different terephthalate polyesters can be depolymerized under the disclosed conditions, including PET and PBT. See claims 6 and 7. Alabduhlrahman does not explicitly teach that mixtures of PET and PBT can be used. Nor does Alabduhlrahman explicitly teach that another type of polymer can be included, such as one of those in claim 17 . Jehanno teaches that thermally stable guanidine salt TBD:MSA (methanesulfonic acid) can be used to depolymerize mixed plastics, the polyester PET and the Bisphenol A-based polycarbonate (BPA-PC) in the presence of ethylene glycol: . See abstract and Scheme 1 on p. 6711. The TBD:MSA salt is analogous to those taught in Alabduhlrahman , wherein the carboxylic acid is methanesulfonic acid. Like, Alabduhlrahman , Jehanno teaches that the MSA salt of the TBD is more stable than the free base. It would have been prima facie obvious to combine the teachings of Alabduhlrahman and Jehanno to arrive at the instantly claimed process with a reasonable expectation of success before the effective filing date of the instant invention. A person of ordinary skill would have been motivated to apply the organocatalyst carboxylic acid salts of Alabduhlrahman in a process involving mixed plastics, including at least PET and BPA-PC, because Jehanno teaches that analogous catalysts can effect the depolymerization of both species of polymers in a single reaction. Jehanno further teaches that the depolymerization of mixed plastics without having to separate the plastics is beneficial because it simplifies the plastics recycling process and makes it “greener” and more commercially attractive. See abstract and introduction. Therefore, if the catalysts of Alabduhlrahman were applied to the same system as Jehanno, then the same advantages would predictably be achieved. Double Patenting The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg , 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman , 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi , 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum , 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel , 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington , 418 F.2d 528, 163 USPQ 644 (CCPA 1969). A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA. A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b). The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13. The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA/25, or PTO/AIA/26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer . Claims 1- 7, 11-14, 17, 19, 20, and 22-25 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-22 of co-pending U.S. App. No. 19/059410 (‘410). Although the claims at issue are not identical, they are not patentably distinct from each other because the claims of ‘410 teach an obvious variant of the instantly claimed process wherein the condensation polymer is PET (1) ( claims 17, 19, and 20 ), the protic molecule is an R-functionalized alcohol molecule (2), and the monomer product is of formula (3). In claims 4-5, ‘410 teaches that the base is a compound of formula (1d) in claim 5 , preferably TBD, which falls within the genus of or includes the genus of claims 1-7 . Claims 5-7 of ‘410 further teach that the carboxylic acid is preferably TFA, which falls within the genus of claims 11-14 . Claim 8 of ‘410 teaches that the molar ratio of TBA:TFA is 1:1, which falls within the ranges of instant claims 22-25 . The rejection is provisional because the patentably indistinct claims have not in fact been patented. Claims 8, 9, 15, 16, and 21 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-22 of co-pending U.S. App. No. 19/059410 (‘410), as applied to Claims 1-7, 11-14, 17, 19, 20, and 22-25 above and further in view of Alabdulrahman ( US 2012/0223270 , published on 9/6/2012). The claims of ‘410 do not explicitly teach the bases of claims 8 and 9 or the use of a diol, preferably ethylene glycol of claims 15-16 , to produce the BHET of claim 21 . Alabdulrahman is directed toward the depolymerization of terephthalate polyesters in the presence of a glycol comprising 2 to 5 carbon atoms and an amidine organocatalyst, heating the reaction mixture at a temperature of about 120°C or more to depolymerize the terephthalate polyester, thereby forming a terephthalate reaction product comprising a monomeric dihydroxy terephthalate diester. See abstract and claims. Alabdulrahman teaches the amidine (organic-nitrogen containing base) organocatalysts for the depolymerization with glycols comprising 2 to 5 carbon atoms are of the following formula (2): , wherein the amidine functional group can reside in an acyclic or cyclic structure. Preferably the amidine is DBU (1,2-diazabicyclo[5.4.0]undec-7-ene) or DBN (1,4-diazabicyclo(4.3.0)non-5-ene. See [0041-0046]. DBU corresponds to a compound of structure (1) in claim 1 , wherein X is CR a , R a is H; R 4 is H; R 3 and R 2 are interconnected to form a seven-membered ring, wherein the combination of R 3 and R 2 is an alkylene group having five carbon atoms; R 6 is an electron pair and a double bond is present; and R 5 and R 1 are interconnected to form a six-membered ring, wherein the combination of R 5 and R 1 is an alkylene group having three carbon atoms. Thus, DBU also anticipates the base in claims 2-4 and 9 , wherein the R variables are as defined above and wherein variable r is 1 and variable s is 2. DBN corresponds to an organic nitrogen-containing base of formula (I) of claims 1-4 and formula (1g) in claim 8 , wherein X is CR a , R a is H, R 4 is H, R 3 and R 2 are interconnected to form a five-membered ring, R 1 and R 5 are connected to form a six- membered ring, and R 6 is an electron pair, wherein one of the double bonds is present, and r is 1 and s is 0. Alabdulrahman further teaches reacting PET (polyethylene terephthalate, a polyester and condensation polymer- claims 17, 19, and 20 ) post-consumer waste; with i) a catalyst (DBU-BA) comprising an organic nitrogen containing base (DBU, 1,2-diazabicyclo[5.4.0]undec-7-ene) and a carboxylic acid (BA, benzoic acid) or ii) a catalyst (DBU-TA) comprising DBU and terephthalic acid (TA) as the carboxylic acid in the presence of a protic molecule (ethylene glycol, EG), which is a diol ( claims 15-16 ); at an elevated temperature (190°C) effective for inducing glycolysis (alcoholysis with EG) of the condensation polymer (PET) to produce a monomeric useful breakdown product (BHET, bis(2-hydroxyethyl) terephthalate), claim 21 ) which is capable of being polymerized. See [0079-0084, 0092-0094, 0101, 0103, 0105, 0106, 0135-0137, and 0140-0143]. Alabdulrahman further teaches that when the catalysts are in the salt form that they have greater air and thermal stability at the elevated depolymerization temperature compared to the free base organocatalyst. See [0048-0051] and [0137]. It would have been prima facie obvious for a person of ordinary skill in the art to combine the teachings of ‘410 and Alabdulrahman to arrive at the instantly claimed processes with a reasonable expectation of success before the effective filing date of the claimed invention. A person of ordinary skill would have been motivated to employ other organic nitrogen containing base and carboxylic acid salt catalysts other than those explicitly taught in the claims of ‘410 because Alabdulrahman suggests as much would yield predictable results . Further, Alabdulrahman directs the skilled artisan that when the protic molecule is a glycol, that amidines, such as the DBN and DBU embodiments of claims 1-4 and 8 are superior bases . The rejection is provisional because the patentably indistinct claims have not in fact been patented. Claim 10 is provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-22 of co-pending U.S. App. No. 19/059410 (‘410), as applied to Claims 1-7, 11-14, 17, 19, 20, and 22-25 above and further in view of Burdeniuc (WO 2022/194587A2, published on 9/22/2022, claiming the benefit of priority to PCT/EP2022/055674, filed on 5/7/2022, claiming the benefit of priority to US 63/161693, published on 1/6/2011). The claims of ‘410 do not explicitly teach the use of a base according to instant claim 10 . Budeniuc is directed toward a method for the recycling of organic polymers, preferably PET, to produce useful chemical intermediates based on their monomeric components. See abstract. Budeniuc claims a process for depolymerizing a difunctional alcohol and at least one organic base catalyst and/or carboxylic acid of the same, wherein the at least one organic base catalyst is an alkyl substituted guanidine of the following structure: . See claims 1-2. The alkyl substituted guanidine corresponds to a compound of formula (1i) in claim 10 wherein instant X is N and instant R 3 , R 4 , R 5 , and R 6 are C 1-3 alkyl and instant R 1 is a C1 -3 alkyl or H. It would have been prima facie obvious to combine the teachings of the claimsd of ‘410 and Budeniuc to arrive at the instantly claimed process with a reasonable expectation of success before the effective filing date of the claimed invention. A person of ordinary skill would have been motivated to substitute one of the catalysts of ‘410 for that claimed because Budeniuc teaches that such a catalyst exists and would be expected to provide the desired product with a reasonable expectation of success. Also see MPEP 2143(I)(B). The rejection is provisional because the patentably indistinct claims have not in fact been patented. Claim 18 is provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-22 of co-pending U.S. App. No. 19/059410 (‘410), as applied to Claims 1-7, 11-14, 17, 19, 20, and 22-25 above and further in view of Jehanno (“Selective Chemical Upcycling of Mixed Plastics Guided by a Thermally Stable Organocatalyst” Angew. Chem. Int. Ed. 2021, p. 6710, of record in the IDS filed on 5/10/2023 ). The claims of ‘410 do not explicitly teach a mixed plastic reactant stream. Jehanno teaches that thermally stable guanidine salt TBD:MSA (methanesulfonic acid) can be used to depolymerize mixed plastics, the polyester PET and the Bisphenol A-based polycarbonate (BPA-PC) in the presence of ethylene glycol: . See abstract and Scheme 1 on p. 6711. The TBD:MSA salt is analogous to those taught in the claims of ‘410, wherein the carboxylic acid is methanesulfonic acid. It would have been prima facie obvious to combine the teachings of the claims of ‘410 and Jehanno to arrive at the instantly claimed process with a reasonable expectation of success before the effective filing date of the instant invention. A person of ordinary skill would have been motivated to apply the organocatalyst carboxylic acid salts of the claims of ‘410 in a process involving mixed plastics, including at least PET and BPA-PC, because Jehanno teaches that analogous catalysts can effect the depolymerization of both species of polymers in a single reaction. Jehanno further teaches that the depolymerization of mixed plastics without having to separate the plastics is beneficial because it simplifies the plastics recycling process and makes it “greener” and more commercially attractive. See abstract and introduction. Therefore, if the catalysts of ‘410 were applied to the same system as Jehanno, then the same advantages would predictably be achieved. The rejection is provisional because the patentably indistinct claims have not in fact been patented. Conclusion Any inquiry concerning this communication or earlier communications from the examiner should be directed to FILLIN "Examiner name" \* MERGEFORMAT AMY C BONAPARTE whose telephone number is FILLIN "Phone number" \* MERGEFORMAT (571)272-7307 . The examiner can normally be reached FILLIN "Work Schedule?" \* MERGEFORMAT 11-7 . Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice. If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, FILLIN "SPE Name?" \* MERGEFORMAT Scarlett Goon can be reached at FILLIN "SPE Phone?" \* MERGEFORMAT 571-270-5241 . The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300. Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000. /AMY C BONAPARTE/ Primary Examiner, Art Unit 1692
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Prosecution Timeline

Jan 13, 2023
Application Filed
Dec 17, 2025
Non-Final Rejection — §102, §103, §112 (current)

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