DETAILED ACTION
Status of Application
This action is responsive to national-stage application filed 02/28/2023. Following entry of the preliminary amendment filed 12/14/2023, claims 1-2, 4-24, and 27-37 are currently pending and under examination herein.
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 . However, 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 a 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.
Information Disclosure Statement(s)
The information disclosure statement(s) (IDS) filed on 05/19/2023, 09/08/2025 and 09/30/2025 are in compliance with the provisions of 37 CFR 1.97, 1.98 and MPEP § 609, and therefore the information referred to therein has been considered as to the merits. Initialed copies of the IDS are included with the mailing/transmittal of this Office action.
Claim Interpretation
With respect to Claims 1 and 2, the Office is construing the term “low boiling conjugated diene” to mean a conjugated diene having a boiling point of less than 200oC, in accordance with the broadest definition provided herein; see paragraph [0062] of the as-filed specification.
Objection – Claims
Claim 1 is objected to because of the following informalities: referring to line 9, it is presumed “ration” was intended to read –ratio-- (cf., claim 2, line 8).
Claims 1 and 2 are objected to because of the following informalities: insertion of –are-- after “conjugated diene” in lines 9 and 7 of the respective claims (i.e., “hydrogen and the … conjugated diene are co-fed …”) is recommended for grammatical clarity.
Claim 2 is objected to under 37 CFR 1.75 as being a substantial duplicate of claim 1. Both claims are drawn to a process of polymerizing conjugated dienes in a hydrocarbon reaction medium within a reactor, and both recite identical manipulative steps to include use of the same LOXSH catalyst comprising one or more σ—µ polar modifiers and co-feeding of the same two gaseous and/or volatile compounds comprising hydrogen and low boiling conjugated diene. See claim 1, lines 3-13 and 15 and cf., claim 2, lines 2-11. It is noted that claim 1 also recites “c) polymerizing at least a portion of the conjugated diene,” in line 14. While this step is not positively recited in claim 2, the stated purpose of the claimed process is “for hydrogen mediated polymerization of conjugated dienes”; see claim 2, lines 1-2. Therefore, a corresponding “polymerizing” step is regarded as a necessary and inevitable reaction when performing the process of claim 2. Similarly, though not positively recited in claim 1, “hydrogen mediated” polymerization as per claim 2 is considered an intrinsic effect of the co-feeding of hydrogen and the low boiling conjugated diene to form a polymerization reaction mixture as per step b) of claim 1. Should the Applicant disagree, it is requested that Applicant identify at least one process embodiment that fulfills all the requirements of claim 1 but does not literally infringe claim 2.
Claims 5-7 are objected to because of the following informalities: the abbreviation “CD” in each claim should be defined at its first occurrence in the claims, as by inserting --(CD)-- after “conjugated diene” in lines 9 and 7 of claims 1 and 2, respectively.
Claims 18 and 27 are objected to because of the following informalities: redundant recitations of “N,N-dimethylaminoethanol” and “dimethylaminoethanol” in each claim. See claim 18, lines 2 and 10, and claim 27, lines 7 and 15. The two chemical names are synonyms for the same compound as evidenced by the submission from Chemical Book (cited herewith); see page 1/6, under [Synonyms]. Therefore, the latter recitation appears superfluous and should be deleted.
Claim 24 is objected to because of the following informalities: referring to line 8, it is presumed “move” was intended to read –more-- (i.e., one or more of …).
Appropriate correction of the aforementioned claims is required.
Claim Rejections – 35 U.S.C. 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 1 and 4-24 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 1, the claim provides the limitation to “the LOXSH reagent” in the final line. There is no proper and sufficient antecedent basis for this limitation in the claim. To cure the antecedent basis problem, it is suggested that “reagent” be amended to –catalyst-- (cf., claim 1, lines 3-4). Dependent claims 4-21 inherit the indefiniteness ascribed to parent claim 1.
Regarding Claim 22, the claim is drawn to an LOXSH catalyst or reagent composition comprising recited components 1), 2) and 3), with component 3) – “optionally elemental hydrogen and/or an organo silicon hydride” – being a non-essential (optional) constituent. However, the Applicant has defined the terms “LOXSH” to mean a lithium alkoxide complexed saline hydride catalyst (cf., claim 1, lines 3-4) and “saline hydride” to signify the presence of hydrogen as a negatively charged ion, H- (see ¶ [0050] of as-filed specification). Accordingly, where the claimed composition comprises only recited components 1) and 2), there is uncertainty as to the source of H- ions needed to form the “LOXSH catalyst” being claimed. Clarification at least by way of explanation is required.
Dependent claims 23-24 are subsumed in this ground of rejection as both claims read on the corresponding two-component composition where component 3) is permissibly absent.
Claim Rejections – Statutory Double Patenting
A rejection based on double patenting of the “same invention” type finds its support in the language of 35 U.S.C. 101 which states that “whoever invents or discovers any new and useful process... may obtain a patent therefor...” (Emphasis added). Thus, the term “same invention,” in this context, means an invention drawn to identical subject matter. See Miller v. Eagle Mfg. Co., 151 U.S. 186 (1894); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Ockert, 245 F.2d 467, 114 USPQ 330 (CCPA 1957).
A statutory type (35 U.S.C. 101) double patenting rejection can be overcome by canceling or amending the claims that are directed to the same invention so they are no longer coextensive in scope. The filing of a terminal disclaimer cannot overcome a double patenting rejection based upon 35 U.S.C. 101.
Claims 22-24 are provisionally rejected under 35 U.S.C. 101 as claiming the same invention as that of claims 22-24 of copending Application No. 18/842,184 (reference application; published as US 2025/0179233 A1).
Regarding pending Claim 22, the claim is drawn to an LOXSH catalyst or reagent composition, wherein the composition is selective for 1,4-CD monomer microstructure enchainment, and the composition comprises 1) at least one tertiary amino alcohol σ—µ polar modifiers having a 2o or a 3o alcohol functional group; 2) an organolithium compound; and 3) optionally elemental hydrogen and/or an organo silicon hydride. Copending claim 22 is likewise drawn to an LOXSH catalyst or reagent composition comprising the very same respective components 1), 2) and 3), and further recites “wherein the composition is selective for 1,4-CD monomer microstructure enchainment in a VA-CD copolymer composition”. While pending claim 22 does not mention enchainment in a VA-CD copolymer, it must necessarily be the case that the corresponding selectivity in said copolymer is an intrinsic property of the presently claimed composition, based on the identity of the mutually claimed compositional components. Therefore, the pending and copending claims are deemed to be drawn to the same invention.
Regarding pending Claim 23, the recited structures IV, III, VI, VII, V, and IX correspond identically to respective structures IV, III, VI, VII, V, and IX as set forth in copending claim 23.
Regarding pending Claim 24, the claim is coextensive in scope with copending claim 24 with respect to the mutually recited species of σ—µ polar modifier.
This is a provisional statutory double patenting rejection since the claims directed to the same invention have not in fact been patented.
Claim Rejections – Nonstatutory 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 27-29 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 25 and 27-29 of copending Application No. 18/842,184 (reference application; published as US 2025/0179233 A1).
Although the claims at issue are not identical, they are not patentably distinct from each other because of the substantial overlap in scope of the mutually claimed subject matter.
In particular as to pending claim 27, the claim is drawn to an LOXSH catalyst or reagent composition comprising: a) at least one tertiary amino alcohol σ—µ or amino-ether-alcohol polar modifier; b) at least one separate σ—µ polar modifier; c) an organolithium compound; and d) elemental hydrogen and/or an organo silicon hydride. Copending claim 25 is also drawn to an LOXSH catalyst or reagent composition comprising the same respective components a) – d) where optional components b) and d) are present. Claim 27 further recites wherein the σ—µ polar modifiers of the composition comprises I) about 50 mole% or more, but less than 100 mole% of a tertiary amino alcohol or a tertiary amino-ether-alcohol σ—µ polar modifier selected from one or more of an enumerated list of specific compounds; and II) from about 50 mole% to greater than 0 mole% of one or more of an ether-alcohol σ—µ polar modifier selected from another enumerated list of specific compounds (see claim 27, line 7 et seq.). Copending claim 27 is drawn to the LOXSH composition of claim 25 and recites that the σ—µ polar modifier of the reagent comprises between about 50 mole% to less than 100 mole% of a tertiary amino alcohol or a tertiary amino-ether-alcohol σ—µ polar modifier selected from one or more of a list of specific compounds which is coextensive with the list I) of pending claim 27; and from about 50 mole% to greater than 0 mole% of a tertiary amino alcohol or a tertiary amino-ether-alcohol σ—µ polar modifier selected from one or more of another list of specific compounds which is coextensive with the list II) of pending claim 27. Therefore, copending claim 27/25 anticipates the scope of pending claim 27. Accordingly, it would have been obvious to one of ordinary skill in the art to practice pending claim 27 when in possession of copending application claims 27/25.
Regarding pending Claims 28-29, the claims are coextensive in scope with copending claims 28 and 29, respectively, with respect to the mutually recited ratios for total AA and/or AEA to the total separate EE σ—µ polar modifier ([AA + AEA]:EA).
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Claim Rejections – 35 U.S.C. 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.
Claims 22-24 are rejected under 35 U.S.C. 103 as being unpatentable over Layman (WO 2017/176740A1).
Regarding Claims 22-24, reference to Layman relates to LOXSH catalyst for hydrogen mediated anionic chain transfer polymerization of vinyl aromatic monomers (¶¶ [031]-[034]). Layman generally teaches that the LOXSH catalyst is formed from: (i) molecular hydrogen; (ii) an organolithium compound with or without an organomagnesium compound; (iii) optionally a polytertiaryamine compound; (iv) a tertiary amino alcohol and/or a tertiary amino ether-alcohol and/or a ether-alcohol; (v) an optional solid alkali or alkaline earth metal hydride or an alkali metal or alkali metal alloy (vi) optionally an aromatic hydrocarbon having at least one C-H covalent bond pKa within the range of 2.75 pKₐ units above that of the pKₐ of toluene to -4.30 pKₐ units below the pKₐ of toluene; and in (vii) a hydrocarbon solvent with a pKₐ greater than H₂; wherein the aromatic hydrocarbon and hydrocarbon solvent may be the same or different (¶ [053]). In specific embodiments, Layman illustrates LOXSH catalysts formed with σ—µ polar modifiers having a primary alcohol, in particular N,N-dimethylethanolamine as in Examples 25-28 (¶¶ [0197]-[0198], [0201]).
Layman differs from the present invention in failing to disclose, in a single embodiment, a LOXSH catalyst or reagent composition comprising 1) at least one tertiary amino alcohol σ—µ polar modifiers having a 2o or 3o alcohol functional group. However, Layman does broadly teach that the tertiary amino alcohols or tertiary amino ether-alcohols can be represented by generic structures 5 – 11 as set forth in paragraph [065], wherein structure 7 depicts a polar modifier having a 2o alcohol functional group and structure 5 encompasses aforementioned N,N-dimethylethanolamine.
All structures listed as representative tertiary amino alcohols or tertiary amino ether-alcohols in Layman are considered viable equivalents for the purposes of the reference. Accordingly, it would have been obvious to one of ordinary skill in the art to substitute N,N-dimethylethanolamine by a homologous/isomeric polar modifier having a 2o alcohol functional group, such as 1-dimethylamino-2-propanol, a σ—µ polar modifier species embraced by instant structure IV [for claim 23] and recited in claim 24. Based on their close structural and chemical similarity, one would have reasonably expected these polar modifiers to possess similar properties, including similar utility as the polarizing complexing agent of Layman. The expectation of equivalent performance would have provided the requisite motivation for one of ordinary skill in the art to so modify the disclosed LOXSH catalyst. Indeed, structural relationships, particularly when coupled with a common utility (here, as initiator of hydrogen mediated saline hydride polymerization processes, see ¶ [031]) may provide the requisite motivation or suggestion to modify known compounds to obtain new compounds, see MPEP § 2144.08II(c). Thus, the subject matter of claims 22-24 would have been prima facie obvious to a person having ordinary skill in the art before the effective filing date of the claimed invention.
Claim Rejections – 35 U.S.C. 102/103
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.
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.
Claim 30 is rejected under 35 U.S.C. 102(a)(1) as anticipated by or, in the alternative, under 35 U.S.C. 103 as obvious over either of Shirai et al (US 2012/0202910 A1) (‘Shirai’) and Hargis et al (US 5216181) (‘Hargis’).
Regarding Claim 30, Shirai describes describe a polybutadiene composition having a microstructure ratio of 1,2-structure/1,4-structure ranging from 55/45 to 80/20 (% by mole) and a number average molecular weight Mn ranging from 500 to 20,000, and also describes that the composition has a glass transition temperature Tg from about -120oC to about -20oC; e.g., -58oC (see Examples 1, 5, 6, and 8 and Table 3: Example 8 (¶ [0137]). Separately, Hargis describes telechelic polybutadiene compositions having a number average molecular weight Mn, a 1,4-CD microstructure content (Trans + Cis) and a glass transition temperature Tg as per claimed characteristics 1), 3) and 4), respectively (see col. 8, Example 2 and Table II, Run Nos. 2, 4 and 5). Neither Shirai nor Hargis explicitly report Brookfield viscosity; however, since the compositions in each instance are liquid resins (see, e.g., Shirai, Example 4, ¶ [0104] and Hargis at col. 7, line 54 et seq.), it plausible to infer that the Brookfield viscosity of the respective compositions falls within the claimed range of about 20 to about 200,000 cP. Further, while neither Shirai nor Hargis teaches a “hydrogen mediated” anionic polymerization process, it is not clear from the present record that such a process limitation necessarily leads to a different polymer structure as those respectively disclosed by Shirai and Hargis, apart from the shared characteristics of Mn, viscosity (implicitly), microstructure, and Tg. In this regard, it should be noted that a difference in preparation, to be of patentable significance, must result in a substantially different product than that obtained by the prior art process. See MPEP § 2113.
Pertinent Art
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. House et al (US 3352934) is cited as pertinent to use of hydrogen to control molecular weight of liquid copolymers of butadiene and styrene prepared by solution polymerization in the presence of alkali metal catalyst (note Abs., Examples 1-2). The citation does not teach the present invention, especially use of a LOXSH catalyst or reagent composition comprising one or more σ—µ polar modifiers.
Potentially Allowable Subject Matter
Claims 1-2 and 4-21 would be allowable if amended or rewritten to overcome the objections and rejection under 35 U.S.C. 112 set forth in this Office action.
Claims 27-29 are deemed free of the prior art and would be allowable if amended or rewritten to overcome the objection set forth in this Office action (re: claim 27) and upon resolution of the provisional double-patenting rejection supra.
Claims 31-37 are objected to as being dependent on a rejected base claim, but would be allowable if rewritten in independent form including all the limitations of the base claim and any intervening claim.
The following is a statement of reasons for the indication of allowable subject matter:
Regarding claims 1-2 and 4-21, the closest prior art to Layman, discussed above, does not describe the inventions of said claims, especially the co-feeding of hydrogen and the low boiling conjugated diene to form a polymerization reaction mixture as per step b) of claim 1 (identically recited in claim 2, line 5 et seq.), or provide proper rationale to modify its disclosed invention into the invention of any of claims 1-2 and 4-21.
Regarding claims 27-29, the closest prior art to Layman, discussed above, does not describe the inventions of said claims, especially a LOXSH catalyst or reagent composition comprising recited components a), b), c) and d), wherein the σ—µ polar modifiers of the composition comprises mole% proportions I) and II) as per claim 27, line 5 et seq., or provide proper rationale to modify its disclosed invention into the invention of any of claims 27-29.
Regarding claims 31-37, the closest prior art to Shirai et al and Hargis et al, discussed above, does not describe the inventions of said claims, especially a hydrogen mediated polyisoprene having one of claimed parameters 1, 2) or 3) as per claim 31/30, or a composition having one of claimed parameters 1), 2) or 3) as per claim 32/30 or 33/30, or a composition having a molar ratio of vinyl-1,2:VCP (vinylcyclopentane) as per claims 34-37/30, or provide proper rationale to modify their respective inventions into the invention of any of claims 31-37.
Correspondence
Any inquiry concerning this communication should be directed to Examiner F. M. Teskin whose telephone number is (571) 272-1116. The examiner can normally be reached on Monday through Friday from 9:00 AM - 5:30 PM.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner's supervisor, Robert Jones, can be reached at (571) 270-7733. The appropriate fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/FRED M TESKIN/Primary Examiner, Art Unit 1762
/FMTeskin/12-19-25
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