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 Interpretation
The instant specification defines many terms, including (submitted specification paragraph 56, 57):
The terms “oligomers” and “oligomeric units” refer, unless otherwise stated, to linear or branched molecules made up of short chains of from 2 to 40 repeating monomeric units.
The term “oligomeric macromonomer” refers, unless otherwise stated, to an adduct resulting from a reaction of a moiety of one or more monomeric units of an oligomer with another compound.
The term “functionalized,” in the context of cycloalkenes, refers, unless otherwise stated, to a cycloalkene being ring-strained or having a nonhydrocarbon substituent on one or more of the carbons of the cyclic moiety of the cycloalkene.
The term “ring-strained,” in the context of cycloalkenes, refers, unless otherwise stated, to the relative higher energy of a cycloalkene as a result of the number of carbons making up one or more of the cyclic moieties of the cycloalkene causing compression or “strain” to the natural angles between carbon-carbon bonds at each carbon atom of the one or more cyclic moieties, wherein the compression or strain would be alleviated (and the energy would be decreased) were the one or more cyclic moieties to undergo a reaction that would “open” the ring at the alkene bond.
See specification for full list of definitions.
Specification
The disclosure is objected to because of the following informalities: in the specification submitted 5/1/23, p.20 in paragraph 84 the depicted structure is incorrectly identified as 1,5-dicyclopentadiene. The structure depicted is 1,5-cyclooctadiene (not 1,5-dicyclooctadiene as is mentioned elsewhere in paragraph 84). Applicant may correct the structure and/or the name to fit what is otherwise already present in paragraph 84.
Appropriate correction is required.
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) 13-15 is/are rejected under 35 U.S.C. 103 as being unpatentable over JP 2003055442 by Goto et al.
Goto describes a method for manufacturing a polymer.
Regarding claim 13, Goto describes endothermically reacting (temperature 40-140C, translation p.6 paragraph 5) cyclopentadiene oligomer (reads on “oligomeric units”, p.3 final paragraph) with a compound (“norbornene-based monomer”, p.3 paragraph 2) to produce an oligomeric macromonomer (“it polymerizes”, p.3 paragraph 2). An additional monomer may be functionalized (p.4 paragraph 7 e.g. epoxy, bromo, methoxy, etc), or norbornene may be functionalized (p.3 paragraph 3-6) leading to a functionalized cycloalkenyl moiety on the “oligomeric macromonomer”. The “oligomeric units”- cyclopentadiene oligomer- are not functionalized or ring-strained (p.3 final paragraph only mentions specific oligomers based on cyclopentadiene).
It would be obvious to one of ordinary skill to choose one of the functionalized norbornenes or add a functionalized monomer to arrive at the functionalized “oligomeric macromonomer” because Goto describes the functionalized monomers as possibilities.
Regarding claim 14, Goto describes adding optionally a cyclooctadiene, cyclopentadiene (p.4 paragraph 6).
Regarding claim 15, Goto describes heating to 40-140C (p.6 paragraph 5). In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990), In re Geisler, 116 F.3d 1465, 1469-71, 43 USPQ2d 1362, 1365-66 (Fed. Cir. 1997). It would be obvious to one of ordinary skill to arrive at values in the claimed range because Goto describes values overlapping with the claimed range.
Allowable Subject Matter
Claims 1-12, 17-20 are allowed.
Claim 16 is objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
Claim 1 is an independent claim to a method involving deconstructing a first polymer to oligomers then reacting those cycloalkenyl-containing oligomers to produce a second polymer. The field of polymeric chemical recycling is sparsely documented compared to other polymeric fields. Depolymerization to oligomer and repolymerization of polyesters like polyethylene terephthalate has been explored, for example in US 20250154333 by Saha et al. It has also been documented more recently in polyolefin elastomers, for example in WO 2025061945 by Chinta et al (paragraph 6). Neither of these describe the presence of cycloalkenyl moieties.
Claims 2-12 depend on claim 1 and are allowable for the same reason.
Claim 16 depends on claim 13 and describes a mass difference between the oligomeric macromonomers and oligomeric units. The specific difference depends on the macromonomers being synthesized in a specific pattern of oligomeric units, and there is not evidence that the closest art of record JP 2003055442 by Goto et al-applied to claim 13 above in 103 rejection- adheres to the pattern.
Claim 17 describes polymerizing oligomers containing functionalized cycloalkenyl moieties via a phosphite ester and a catalyst. Related yet inapplicable art includes “Scalable Frontal Oligomerization: Insights from Advanced Mass Analysis” by Suslick et al. Suslick describes creation of functionalized oligomers of dicyclopentadiene; this art does not have a publication date which allows it to be applied as prior art. Suslick describes using a phosphite ester in catalyzing the oligomerization (p.8235 Fig.1A). Other related yet inapplicable art includes “Rapid energy-efficient manufacturing of polymers and composites via frontal polymerization” by Robertson et al. Robertson describes the phosphite esters as useful for polymerization of dicyclopentadiene (p.223 col 2 paragraph 3-4, p.24 Fig 1a), but not the oligomeric macromonomer or the cleavable aspect.
Claims 18-20 depend on claim 17 and are allowable for the same reason.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to CHRISTINA W ROSEBACH whose telephone number is (571)270-7154. The examiner can normally be reached 8am-3:30pm.
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/CHRISTINA H.W. ROSEBACH/ Examiner, Art Unit 1766