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 without traverse of Group II, claims 8-18 in the reply filed on 9/10/2026 is acknowledged.
Claims 1-7, 19, and 20 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on 9/10/2026.
Claim Interpretation
Claim 8 pertains to a method for preparing the monomer composition of claim 1. The structural features of claim 1 are construed as limiting the scope of the method claim, whereby the protocol of claim 8 requires that one prepares a composition with the impurity characteristics of claim 1. MPEP 2111.02.
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 8-18 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.
Claim 8 requires the structural features of claim 1 by reference. In this regard, the scope of the claim is unclear as there is insufficient delineation between the “aromatic diol compound” and “aromatic diol compound derivative” terminology. It is unclear what the full metes and bounds of the term “derivative” is within the context of the claim and which compounds fall within and outside the term. The lack of an explicit definition of what does, or does not, constitute a “derivative” within the specification is noted, particularly in what manner the “derivative” serves to differ in scope from an “aromatic diol compound”. Per MPEP 2173.04, a broad claim is not indefinite merely because it encompasses a wide scope of subject matter provided the scope is clearly defined. But a claim is indefinite when the boundaries of the protected subject matter are not clearly delineated and the scope is unclear. For example, a genus claim that covers multiple species is broad, but is not indefinite because of its breadth, which is otherwise clear. But a genus claim that could be interpreted in such a way that it is not clear which species are covered would be indefinite (e.g., because there is more than one reasonable interpretation of what species are included in the claim).
Claim 8 uses the terminology “glycol-based compound”. It is unclear what is meant or implied by the modifier “based” and how such compounds deviate otherwise from “glycol compounds”. The lack of an explicit definition of what does, or does not, constitute a “based” compound within the specification is noted. Accordingly, the intended scope of the claim is unclear.
Per claim 1, the monomer composition is recovered from a “polycarbonate-based resin”. Claim 8 requires depolymerization of “polycarbonate”. It is unclear whether or not these terms are meant to be one in the same. It is unclear what is meant or implied by the modifier “based” and how such polycarbonates deviate otherwise from “polycarbonates”.
As claims 9-18 depend from claim 8, they are rejected for the same issues discussed above.
Claim 13 uses the terminology “amidine-based salt compound”. It is unclear what is meant or implied by the modifier “based” and how such compounds deviate otherwise from “amidine salt compounds”. The lack of an explicit definition of what does, or does not, constitute a “based” compound within the specification is noted. Accordingly, the intended scope of the claim is unclear.
As claims 14-16 depend from claim 13, they are rejected for the same issue discussed above.
Claim 15 recites “the fused ring comprises a fused ring between a 7-membered ring and a 6-membered ring”. It is unclear whether the limitation is meant to require a system where a second fused ring system bridges a 7-membered ring and a 6-membered ring or if it is simply indicating the fused system comprises fused 6- and 7- membered rings. Therefore, the intended scope of the claim is unclear.
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(s) 8-12 and 17 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Iannone (J. Mol. Cat. A: Chem. 2017, 425, 107-116; cited 2/29/2024).
Regarding Claims 8-10, Iannone describes processes of depolymerizing polycarbonates using ionic liquids/ZnO catalysts (Abstract) and describes embodiments where polycarbonate, propylene glycol, tetrahydrofuran, and catalyst are combined and stirred to obtain bisphenol A (Table 1). Polycarbonate is first added to THF to form mixed solution, after which catalyst and nucleating agent (glycol) is added/stirred (Section 2.3 of Page 108). 100% selectivity is reported (Table 1), suggesting less than 0.5 mol% of derivative impurities.
Regarding Claim 11, Iannone teaches 5 mL of THF (~ 4.44 g) relative to 1.06 g of glycol (Table 1), equivalent to a 4.2:1 ratio.
Regarding Claim 12, Iannone describes embodiments where 1 mmol / 0.254 g of polycarbonate is used with 5 mol% nBu4Cl ionic liquid catalyst (molecular weight: 278 g/mol), equivalent to roughly 5.5 pbw catalyst per 100 pbw polycarbonate.
Regarding Claim 17, Iannone teaches embodiments where stirring occurs at 100 degrees C for 3-7 hours (Table 1).
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.
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) 8-17 is/are rejected under 35 U.S.C. 103 as being unpatentable over Park (KR 2022-0023451A). As the cited KR publication is in a non-English language, a machine-translated version of the publication will be cited to.
Park names additional inventors not listed as inventors within the present application. Therefore, Park is treated as prior art under 35 USC 102(a)(1). See MPEP 2153.01(a).
Regarding Claims 8, 10, 13, and 17, Park teaches methods of making highly pure bisphenol A from polycarbonates using amidine catalysts (Page 2). Examples are taught where methylene chloride (organic solvent), alcohol, and ionic liquid amidine catalyst is combined stirred and subsequently polycarbonate is added to promote depolymerization at 40 degrees C for 5 hours (Pages 13 and 15). Park teaches the alcohols used can be C1-C4 alcohol or diols/glycols (Page 12). While not indicating the content of derivative impurities, Park is seen to suggest substantially the same materials, catalysts, and depolymerization conditions. Accordingly, the content of derivative impurities is seen to necessarily be exhibited by the protocols of Park in the absence of evidence to the contrary.
Park differs from the subject matter claimed with respect to the order of mixing ingredients, whereby the claims require adding polycarbonate to organic solvent prior to further addition of glycol and catalyst. It has been held that the selection of any order of mixing ingredients is prima facie obvious in the absence of a showing of criticality with respect to the order claimed. MPEP 2144.04(IV)(C). In light of the cited case law therein, it would have been obvious to one of ordinary skill in the art that any order of mixing ingredients, inclusive of mixing organic solvent and polycarbonate first and followed by glycol and base, can be performed within the protocols of the prior art to predictably afford bisphenol A monomers for re-use in the absence of evidence of criticality with respect to the order claimed.
Regarding Claim 9, Park teaches glycols of the structure OH-CH(R4)-CH(R5)-OH, where R4 and R5 can be independently hydrogen, alkyl, or cycloalkyl (Page 12), construed as alkylene glycol.
Regarding Claim 11, Park teaches 60 mL of dichloromethane (~ 80 g) is used with 30 mL alcohol (methanol; ~ 24g) (Page 15), equivalent to an organic solvent:glycol ratio of 3.33:1.
Regarding Claim 12, Park teaches 1.5 g of amidine catalyst per 30 g of polycarbonate (Page 15), equivalent to 5 pbw catalyst per 100 pbw polycarbonate.
Regarding Claims 14-16, Park teaches the use of catalyst:
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(Pages 13 and 15), consistent with the ionic liquids claimed.
Claim(s) 18 is/are rejected under 35 U.S.C. 103 as being unpatentable over Park (KR 2022-0023451A) in view of Nikje (Polimery 2011, 56, nr 5, 381-384). As the cited KR publication is in a non-English language, a machine-translated version of the publication will be cited to.
The discussion with respect to Park within ¶ 24-30 is incorporated herein by reference.
Regarding Claim 18, Park differs from the subject matter claimed in that purificiation via crystallization solvent is not described. Nikje also pertains to the depolymerization of polycarbonates with glycols (Abstract; Recycling process of page 382). Nikje notes after depolymerization, obtained bisphenol A can be precipitated with water and then subject to further recrystallization and filtration for purification (Page 382). It would have been obvious to one of ordinary skill in the art to inject the bisphenol A product obtained from Iannone into water crystallization solvent, recrystallizing, and filtering, because doing so would afford purified bisphenol A crystals as taught by Nikje.
Claim(s) 8-18 is/are rejected under 35 U.S.C. 103 as being unpatentable over Park (KR 2022-0023451A) in view of Gorman (WO 2020/256234 A1). As the cited KR publication is in a non-English language, a machine-translated version of the publication will be cited to.
Park names additional inventors not listed as inventors within the present application. Therefore, Park is treated as prior art under 35 USC 102(a)(1). See MPEP 2153.01(a).
Regarding Claims 8, 10, 13, 17, and 18, Park teaches methods of making highly pure bisphenol A from polycarbonates using amidine catalysts (Page 2). Examples are taught where methylene chloride (organic solvent), alcohol, and ionic liquid amidine catalyst is combined stirred and subsequently polycarbonate is added to promote depolymerization at 40 degrees C for 5 hours (Pages 13 and 15). Park teaches the alcohols used can be C1-C4 alcohol or diols/glycols (Page 12).
Park differs from the subject matter claimed with respect to the order of mixing ingredients, whereby the claims require adding polycarbonate to organic solvent prior to further addition of glycol and catalyst. It has been held that the selection of any order of mixing ingredients is prima facie obvious in the absence of a showing of criticality with respect to the order claimed. MPEP 2144.04(IV)(C). In light of the cited case law therein, it would have been obvious to one of ordinary skill in the art that any order of mixing ingredients, inclusive of mixing organic solvent and polycarbonate first and followed by glycol and base, can be performed within the protocols of the prior art to predictably afford bisphenol A monomers for re-use in the absence of evidence of criticality with respect to the order claimed.
Park also differs from the subject matter claimed in that purificiation via crystallization solvent is not described. Gorman also pertains to the isolation of bisphenol A via polycarbonate depolymerization from alcohol/co-solvent mixtures (Abstract). Gorman teaches it was known purified bisphenol A crystals can be achieved via addition of acidic water mixtures, upon which bisphenol A crystalizes out and can be isolated via filtration (¶ 26). Second recrystallizations can occur with other solvent mixtures afterwards (¶ 26). Gorman notes such protocols gives bisphenol A purities in excess of 99.8% (¶ 28). It would have been obvious to one of ordinary skill in the art to inject bisphenol A product into the crystallization solvents of Gorman and subsequently filtering said crystals, thereby predictably affording bisphenol A of high purity in accordance with the teachings of Gorman. The purity range taught by Gorman is within the scope of the ranges of claim 1.
Regarding Claim 9, Park teaches glycols of the structure OH-CH(R4)-CH(R5)-OH, where R4 and R5 can be independently hydrogen, alkyl, or cycloalkyl (Page 12), construed as alkylene glycol.
Regarding Claim 11, Park teaches 60 mL of dichloromethane (~ 80 g) is used with 30 mL alcohol (methanol; ~ 24g) (Page 15), equivalent to an organic solvent:glycol ratio of 3.33:1.
Regarding Claim 12, Park teaches 1.5 g of amidine catalyst per 30 g of polycarbonate (Page 15), equivalent to 5 pbw catalyst per 100 pbw polycarbonate.
Regarding Claims 14-16, Park teaches the use of catalyst:
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(Pages 13 and 15), consistent with the ionic liquids claimed.
Claim(s) 18 is/are rejected under 35 U.S.C. 103 as being unpatentable over Iannone (J. Mol. Cat. A: Chem. 2017, 425, 107-116; cited 1/25/2024) in view of Nikje (Polimery 2011, 56, nr 5, 381-384).
Iannone describes processes of depolymerizing polycarbonates using ionic liquids/ZnO catalysts (Abstract) and describes embodiments where polycarbonate, propylene glycol, tetrahydrofuran, and catalyst are combined and stirred to obtain bisphenol A (Table 1). Polycarbonate is first added to THF to form mixed solution, after which catalyst and nucleating agent (glycol) is added/stirred (Section 2.3 of Page 108). 100% selectivity is reported (Table 1), suggesting less than 0.5 mol% of derivative impurities.
Regarding Claim 18, Iannone differs from the subject matter claimed in that purificiation via crystallization solvent is not described. Nikje also pertains to the depolymerization of polycarbonates with glycols (Abstract; Recycling process of page 382). Nikje notes after depolymerization, obtained bisphenol A can be precipitated with water and then subject to further recrystallization and filtration for purification (Page 382). It would have been obvious to one of ordinary skill in the art to inject the bisphenol A product obtained from Iannone into water crystallization solvent, recrystallizing, and filtering, because doing so would afford purified bisphenol A crystals as taught by Nikje.
Claim(s) 8-12, 17, and 18 is/are rejected under 35 U.S.C. 103 as being unpatentable over Iannone (J. Mol. Cat. A: Chem. 2017, 425, 107-116; cited 1/25/2024) in view of Gorman (WO 2020/256234 A1).
Regarding Claims 8-10 and 18, Iannone describes processes of depolymerizing polycarbonates using ionic liquids/ZnO catalysts (Abstract) and describes embodiments where polycarbonate, propylene glycol, tetrahydrofuran, and catalyst are combined and stirred to obtain bisphenol A (Table 1). Polycarbonate is first added to THF to form mixed solution, after which catalyst and nucleating agent (glycol) is added/stirred (Section 2.3 of Page 108).
Iannone differs from the subject matter claimed in that purificiation via crystallization solvent is not described. Gorman also pertains to the isolation of bisphenol A via polycarbonate depolymerization from alcohol/co-solvent mixtures (Abstract). Gorman teaches it was known purified bisphenol A crystals can be achieved via addition of acidic water mixtures, upon which bisphenol A crystalizes out and can be isolated via filtration (¶ 26). Second recrystallizations can occur with other solvent mixtures afterwards (¶ 26). Gorman notes such protocols gives bisphenol A purities in excess of 99.8% (¶ 28). It would have been obvious to one of ordinary skill in the art to inject bisphenol A product into the crystallization solvents of Gorman and subsequently filtering said crystals, thereby predictably affording bisphenol A of high purity in accordance with the teachings of Gorman. The purity range taught by Gorman is within the scope of the ranges of claim 1.
Regarding Claim 11, Iannone teaches 5 mL of THF (~ 4.44 g) relative to 1.06 g of glycol (Table 1), equivalent to a 4.2:1 ratio.
Regarding Claim 12, Iannone describes embodiments where 1 mmol / 0.254 g of polycarbonate is used with 5 mol% nBu4Cl ionic liquid catalyst (molecular weight: 278 g/mol), equivalent to roughly 5.5 pbw catalyst per 100 pbw polycarbonate.
Regarding Claim 17, Iannone teaches embodiments where stirring occurs at 100 degrees C for 3-7 hours (Table 1).
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 8-18 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-7 and 12-14 of copending Application No. 18/728,840. Although the claims at issue are not identical, they are not patentably distinct from each other.
Specifically, claim 1 of ‘840 pertains to a method of depolymerizing polycarbonates with alkylene glycol using substantially the same protocol instantly claimed. The same amidine salt ionic liquid catalysts are taught at claim 7. The same depolymerization conditions are also used (Claim 12). Since the same materials and procedure is being performed, it stands to reason the claimed content of derivative impurity in the obtained aromatic diol is necessarily present in the absence of evidence to the contrary. Therefore, the ‘840 claims anticipate the present claims. The remaining limitations claimed are found within the ‘840 claims.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Conclusion
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/STEPHEN E RIETH/Primary Examiner, Art Unit 1759
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