DETAILED ACTION
Citation to the Specification will be in the following format: (S. # : ¶) where # denotes the page number and ¶ denotes the paragraph number of the pre-grant publication corresponding to the application, US 2024/0018333. Citation to patent literature will be in the form (Inventor # : LL) where # is the column number and LL is the line number. Citation to the pre-grant publication literature will be in the following format (Inventor # : ¶) where # denotes the page number and ¶ denotes the paragraph number.
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 .
Status of Application; Restriction
Applicant's election with traverse of Group I (Claims 1-20) in the reply filed on 5/28/2026) is acknowledged. The traversal is on the ground(s) that:
1. The Inventions of Group I and Group II Sould [sic – Should] be examined together.
The Examiner asserts that Group I and Group II "can be made by a materially different process, for example distillation" (Restriction requirement page 2). However, claim 21 is dependent on method of claim 1. The oil composition of claim 21 is not generic but rather a specific metathesis oil composition produced by catalytic olefin cross metathesis in claim 1. Distillation does not and cannot produce the chemically distinct cross-metathesis oligomeric species formed by the catalyzation reaction with the unsaturated compound in claim 1. At best, distillation can separate existing materials, but it cannot perform the metathesis reaction necessary to formulate the metathesis oil composition of claim 21. Under MPEP § 806.05(f), when the examiner alleges a materially different process, the burden shifts to the examiner if the applicant provides a convincing argument that the example is not viable. As distillation alone cannot produce the metathesis oil composition of claim 1 or 21, is not an enabling alternative for the claimed metathesis oil, and as such, Groups I and II are, in fact, not independent or distinct and should be examined together.
(Remarks of 5/28/2026 at 8-9) (emphasis added). In response, Claim 21 is a ““dependent”” claim only in terms of calculating claim fees. Claim 21 is, in fact, drawn to an entirely different class of statutory subject matter under 35 USC 101. It is a product or composition of matter. More specifically, it is a product-by-process claim. An entire body of law and set of proofs exists for this type of claim. These are discussed in MPEP 2113:
I. PRODUCT-BY-PROCESS CLAIMS ARE NOT LIMITED TO THE MANIPULATIONS OF THE RECITED STEPS, ONLY THE STRUCTURE IMPLIED BY THE STEPS
"[E]ven though product-by-process claims are limited by and defined by the process, determination of patentability is based on the product itself. The patentability of a product does not depend on its method of production. If the product in the product-by-process claim is the same as or obvious from a product of the prior art, the claim is unpatentable even though the prior product was made by a different process." In re Thorpe, 777 F.2d 695, 698, 227 USPQ 964, 966 (Fed. Cir. 1985) (citations omitted) (Claim was directed to a novolac color developer. The process of making the developer was allowed. The difference between the inventive process and the prior art was the addition of metal oxide and carboxylic acid as separate ingredients instead of adding the more expensive pre-reacted metal carboxylate. The product-by-process claim was rejected because the end product, in both the prior art and the allowed process, ends up containing metal carboxylate. The fact that the metal carboxylate is not directly added, but is instead produced in-situ does not change the end product.). Furthermore, "[b]ecause validity is determined based on the requirements of patentability, a patent is invalid if a product made by the process recited in a product-by-process claim is anticipated by or obvious from prior art products, even if those prior art products are made by different processes." Amgen Inc. v. F. Hoffmann-La Roche Ltd., 580 F.3d 1340, 1370 n. 14, 92 USPQ2d 1289, 1312, n. 14 (Fed. Cir. 2009). See also Biogen MA Inc. v. EMD Serono, Inc., 976 F.3d 1326, 1334, 2020 USPQ2d 11129 (Fed. Cir. 2020) ("Biogen is certainly correct that the scope of composition and method of treatment claims is generally subject to distinctly different analyses. But where, as here, the novelty of the method of administration rests wholly on the novelty of the composition administered, which in turn rests on the novelty of the source limitation, the Amgen analysis will necessarily result in the same conclusion on anticipation for both forms of claims."); United Therapeutics Corp. v Liquidia Techs., Inc., 74 F.4th 1360, 1373, 2023 USPQ2d 862 (Fed. Cir. 2023) (the court held that product-by-process claims were properly rejected as "anticipated by a disclosure of the same product irrespective of the processes by which they are made."); and Purdue Pharma v. Epic Pharma, 811 F.3d 1345, 117 USPQ2d 1733 (Fed. Cir. 2016). However, in the context of an infringement analysis, a product-by-process claim is only infringed by a product made by the process recited in the claim. Id. at 1370 ("a product in the prior art made by a different process can anticipate a product-by-process claim, but an accused product made by a different process cannot infringe a product-by-process claim").
The structure implied by the process steps should be considered when assessing the patentability of product-by-process claims over the prior art, especially where the product can only be defined by the process steps by which the product is made, or where the manufacturing process steps would be expected to impart distinctive structural characteristics to the final product. See, e.g., In re Garnero, 412 F.2d 276, 279, 162 USPQ 221, 223 (CCPA 1979) (holding "interbonded by interfusion" to limit structure of the claimed composite and noting that terms such as "welded," "intermixed," "ground in place," "press fitted," and "etched" are capable of construction as structural limitations). See also In re Nordt Dev. Co., 881 F.3d 1371,1375-76, 125 USPQ2d 1817, 1820 (Fed. Cir. 2018)(holding "the specification demonstrates that ‘injected molded’ connotes an integral structure," and discussing several cases since Garnero that held "limitations to convey structure even when they also describe a process of manufacture").
MPEP 2113 I (emphasis added). When properly construed, Claim 21 is quite broad. According to the Specification:
[0028] There are several suitable chemical routes to depolymerize the polymeric material, only some of which are alluded to herein. One method to depolymerize the polymeric material includes contacting the polymeric material with an unsaturated compound in the presence of an olefin cross metathesis catalyst and reacting the unsaturated compound with polymeric material in an olefin cross metathesis reaction. The olefin cross metathesis reaction involves chain scission across a carbon-carbon double bond of the polymeric material and the unsaturated compound followed by rearrangement of the fractions of the polymeric material and unsaturated compound to form the olefin cross metathesis product. The chemical identity of the olefin cross metathesis product depends on the chemical identity of the starting polymeric material and unsaturated compound and may include various oligomers of butadiene rubbers, butyl rubbers, isoprene rubber, nitrile rubber, polychloroprene (neoprene), styrene butadiene rubber, polyalkenamers, copolymers of alkenes with conjugated dienes, their functionalized versions and cross-metathesis combinations thereof, for example.
(S. 2: [0028]). The starting polymeric material and unsaturated compound are generic in Claim 1; infinitely broad. Why couldn’t the “oil composition” product of two infinitely broad materials (reasonably construed to include various hydrocarbons) be produced by distillation of crude oil, a complex and variable composition itself? What is actually required of the product described in Claim 1? A double bond? Refineries routinely carry out “PONA” analysis on their crude units. O stands for olefin; i.e. something with a double bond. Perhaps the claims require something else? Note “"[t]he Patent Office bears a lesser burden of proof in making out a case of prima facie obviousness for product-by-process claims because of their peculiar nature" than when a product is claimed in the conventional fashion.” MPEP 2113 I (citations omitted). Furthermore, note “the Patent Office is not equipped to manufacture products by the myriad of processes put before it and then obtain prior art products and make physical comparisons therewith." MPEP 2113 III. Here, the Applicants are claiming infinite polymeric materials and infinite unsaturated compounds, and some manner of metathesis reaction between these two infinitely broad genera. As stated by the CCPA in In re Brown, the Patent Office is not equipped to manufacture infinite products and then compare them to the prior art.
The Examiner requests the Applicants identify the “specific metathesis oil composition” argued in the Remarks, because as understood, this takes a position inconsistent with the Specification, which states it depends on the starting polymeric material and unsaturated compound, which are generic and infinitely broad. This is necessary to treat the matter and to reevaluate the restriction requirement, construe the claims, etc. This should not be burdensome, as Applicants are claiming the ability to be able to characterize the metathesis oil composition (Claim 22).
2. The Inventions of Group I and III Should be Examined Together
The Examiner asserts that Group I and Group III are "directed to related methods." (Restriction Requirement page 2) and have materially different, designs, modes of operation and effects, do not overlap in scope, and are not obvious variants. Applicant respectfully disagrees. Under MPEP § 806.05(), related processes are not distinct if they overlap in scope. Group III utilizes a "metathesis oil composition produced from olefin cross metathesis of a polymeric material and an unsaturated compound," the same "metathesis oil" produced in Group I. As the metathesis oil of Group III is explicitly encompassed by and a product of the depolymerization method of Group I, it cannot be asserted the inventions as claimed "do not overlap in scope". As such, the restriction under 806.050) fails on at least Prong (A) as the inventions of Group I and III are not mutually exclusive and should be examined together.
(Remark of 5/28/2026 at 9). The amendment to Claim 22 tacitly admits that restriction was proper. Narrowing Claim 22 to the method steps of Claim 1 obviates the restriction as previously set forth. The restriction between Groups I and III is WITHDRAWN.
3. The Inventions of Group II and Group III should be examined together.
The Examiner asserts that Group II and Group III are "directed to an unrelated product and process." (Restriction requirement page 3). Applicant respectfully disagrees. Amended claim 22 explicitly recites: "introducing a polymeric material, an unsaturated compound, and an olefin cross metathesis catalyst into a reactor, wherein the polymeric material comprises a carbon black filler". Further, claim 22 also recites: "reacting at least a portion of the polymeric material with the unsaturated compound in the presence of the olefin cross metathesis catalyst to produce at least metathesis oil and metathesis carbon black, wherein the metathesis oil comprises an olefin cross metathesis product of the polymeric material and the unsaturated compound". Further still, claim 22 recites: "quantification of depolymerized species in metathesis oil composition produced from olefin cross metathesis of a polymeric material and an unsaturated compound". By including the method of Group I, and product of Group II of which claim 21 expressly depends upon as noted above, Group III encompasses the limitations of multiple groups (e.g. Groups I, II, and III). Per MPEP § 809, when an application includes a claim that encompasses the limitations of multiple groups, restriction is often improper. The preparation of the metathesis oil is a prerequisite for its subsequent quantification and Claim 22 demonstrates that these are integrated steps in a single process. Because claim 22 defines a single, continuous method from preparation, to product, and thereafter quantification, the groups cannot be directed to unrelated products and processes and should be examined together.
(Remark of 5/28/2026 at 9). This disregards the product-by-process analysis, discussed above. The Examiner repeats the request that the Applicants identify the “specific metathesis oil composition” argued in the Remarks. As understood, the product-by-process claim is infinitely broad, when construed in view of the Applicants own statements in the Specification.
4. Absence of Serious Search Burden
Under MPEP § 803, a restriction is only proper if there is a serious search or examination burden. Applicant contends that the search for the method of Group I (C10G 1/10), the oil composition of Group II (C10L 1/00), and the oil quantification method of Group III (GO1N 1/00) would have substantial overlap. All three CPC classifications center on the same technology; metathesis recycling of filled rubber into oil comprising carbon black filler. As such, no additional search burden is imposed upon the Examiner, aside from routine chemical patent searching. Therefore, examining Group I, Group II, and Group III would not require serious search or examination burden.
For the reasons set forth above, Applicant respectfully submits that the restriction requirement is improper and should be withdrawn as to Groups I, II, and III. Applicant elects Group I (Claims 1-20) for initial examination while maintaining this traversal to preserve the right to petition under 37 CFR § 1.144 and to ensure the potential for rejoinder of the withdrawn claims should the elected claims be found allowable.
(Remarks of 5/28/2026at 10). The ““substantial overlap”” arguments were not developed. Overlap how? What does “substantial” mean? Isn’t claiming in infinitely broad product, the reaction of two infinitely broad starting materials, burdensome enough? Courts have already held that the Patent Office is not equipped to do this. In re Brown, 459 F.2d 531, 535, 173 USPQ 685, 688 (CCPA 1972).
None of this was particularly persuasive.
The Examiner requests Applicants construe Claim 22: what is required; what is excluded, etc.
The Restriction between Group I and III is WITHDRAWN.
The restriction between Groups I, III and Group II is MAINTIANED.
The requirement is still deemed proper and is therefore made FINAL.
Claim(s) 1-22 is/are pending.
Claim(s) 21 is/are withdrawn from consideration.
Claim 21 is withdrawn from further consideration pursuant to 37 CFR 1.142(b), as being drawn to a nonelected product-by-process, there being no allowable generic or linking claim. Applicant timely traversed the restriction (election) requirement in the reply filed on 5/28/2026.
Claim(s) 22 is/are currently amended.
Priority
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Information Disclosure Statement
The information disclosure statement (IDS) submitted on 7/12/2023 is in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statement is being considered by the examiner.
Claim Rejections - 35 USC §§ 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.
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.
I. Claim(s) 1, 2, 3, 4, 6, 7, 9, 10, 16, 17, 18, 19, and 20 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by US 2012/0323037 to Pilard, et al.
With respect to Claim 1, this claim requires “introducing a polymeric material, an unsaturated compound, and an olefin cross metathesis catalyst into a reactor, wherein the polymeric material comprises a carbon black filler.” Pilard teaches tire waste with polymers (i.e. a polymeric material) and carbon black. See e.g. (Pilard 1: [0004]). Unsaturated compounds are taught. (Pilard 2: [0027] – double bond). While Pilard does not use the “olefin cross metathesis catalyst” language in haec verba, Pilard does teach at least Hoveyda-Grubbs catalysts (Pilard 2: [0027]), which the Specification states are “olefin cross metathesis catalysts.” (S. 3: [0030]).
Claim 1 further requires “reacting at least a portion of the polymeric material with the unsaturated compound in the presence of the olefin cross metathesis catalyst to produce at least metathesis oil and metathesis carbon black, wherein the metathesis oil comprises an olefin cross metathesis product of the polymeric material and the unsaturated compound.” The materials are so reacted. (Pilard 3: [0054], [0058]).
Claim 1 further requires “separating at least a portion of the metathesis carbon black.” The carbon black is separated. (Pilard 3: [0054]).
As to Claim 2, butadiene rubbers are taught. (Pilard 1: [0004]; 2: [0032]).
As to Claim 3, at least tire material is taught. (Pilard 1: [0004]; 2: [0032]).
As to Claim 4, cis-2-butene-1,4-diacetate has 8 carbons. (Pilard 2: [0027]). As understood, with the double bond, cis-2-butene-1,4-diacetate would have at least one degree of unsaturation.
As to Claim 6, 2-butene is taught. (Pilard 2: [0027])
As to Claim 7, the Hoveyda-Grubbs catalyst is one example of an organomolybdenum, organotungsten, or organoruthenium catalyst according to the Specification. (S. 3: [0030]). Pilard teaches Hoveyda-Grubbs catalysts. (Pilard 2: [0027]).
As to Claim 9, the temperature is taught. (Pilard 2: [0027]; Claim 1).
As to Claim 10, the pressure is taught. (Pilard Claim 1).
With respect to Claim 16, this claim requires “introducing a polymeric material, a gaseous unsaturated compound, and an olefin cross metathesis catalyst into a reactor, wherein the polymeric material comprises a carbon black filler.” Pilard teaches tire waste with polymers (i.e. a polymeric material) and carbon black. See e.g. (Pilard 1: [0004]). Unsaturated compounds are taught. (Pilard 2: [0027] – double bond). While Pilard does not use the “olefin cross metathesis catalyst” language in haec verba, Pilard does teach at least Hoveyda-Grubbs catalysts (Pilard 2: [0027]), which the Specification states are “olefin cross metathesis catalysts.” (S. 3: [0030]). A reactor is taught. (Pilard 3: [0054]).
Claim 16 further requires “reacting at least a portion of the polymeric material with the gaseous unsaturated compound in the presence of the olefin cross metathesis catalyst at a temperature of about 10°C to about 100°C to produce at least metathesis oil and metathesis carbon black, wherein the metathesis oil comprises an olefin cross metathesis product of the polymeric material and the gaseous unsaturated compound.” The materials are so reacted. (Pilard 3: [0054], [0058]). The temperature is taught. (Pilard 3: [0054]). The product is construed as metathesis oil. Id.
Claim 16 further requires “separating at least a portion of the metathesis carbon black.” The carbon black is separated. (Pilard 3: [0054]).
As to Claim 17, butadiene rubbers are taught. (Pilard 1: [0004]; 2: [0032]).
As to Claim 18, at least tire material is taught. (Pilard 1: [0004]; 2: [0032]).
As to Claim 19, 2-butene is taught. (Pilard 2: [0027])
As to Claim 20, the Hoveyda-Grubbs catalyst is one example of an organomolybdenum, organotungsten, or organoruthenium catalyst according to the Specification. (S. 3: [0030]). Pilard teaches Hoveyda-Grubbs catalysts. (Pilard 2: [0027]).
II. Claim(s) 8 – or as stated below - is/are rejected under 35 U.S.C. 103 as being unpatentable over US 2012/0323037 to Pilard, et al. in view of:
(i) WO 2016/058062 to Dewaele, et al. (2016-04-21; C08G 61/04).
The discussion accompanying “Rejection I” is incorporated herein by reference.
As to Claim 8, to the extent Pilard may not teach the particular species of catalyst claimed, in a similar process, Dewaele teaches Benzylidene-bis(tricyclohexylphosphine)dichlororuthenium as the metathesis catalyst. (Dewaele 9: 4). Use of a known compound (Benzylidene-bis(tricyclohexylphosphine)dichlororuthenium), consistent with its known uses (rubber metathesis, etc.) to achieve predictable results does not impart patentability. MPEP 2143; KSR.
III. Claim(s) 5 – or as stated below - is/are rejected under 35 U.S.C. 103 as being unpatentable over US 2012/0323037 to Pilard, et al. in view of:
(i) Hilf, et al., End Capping Ring-Opening Olefin Metathesis Polymerization Polymers with Vinyl Lactones, J. Am. Chem. Soc. 2008; 130: 11040-11048 (hereinafter “Hilf at __”).
As to Claim 5, Pilard refers to ester transfer agents / unsaturated compounds. (Pilard 2: [0027). To the extent Pilard may not refer to vinyl esters, in a similar process Hilf teaches metathesis reactions with vinyl lactones (vinyl esters) to add functional groups on the polymer chain ends. (Hilf at 11048, col. 2). One of skill in the art would be so motivated to attach carboxylic groups to the ends of polymers, which Hilf teaches “is of great synthetic value.” Id.
IV. Claim(s) 11-15 – or as stated below - is/are rejected under 35 U.S.C. 103 as being unpatentable over US 2012/0323037 to Pilard, et al. in view of:
(i) US 2015/0175754 to Yang, et al.
The discussion accompanying “Rejection I” above is incorporated herein by reference.
With respect to Claim 11, this claim requires “introducing a polymeric material, an unsaturated compound, and an olefin cross metathesis catalyst into a screw extruder, wherein the polymeric material comprises a carbon black filler.” Pilard teaches tire waste with polymers (i.e. a polymeric material) and carbon black. See e.g. (Pilard 1: [0004]). Unsaturated compounds are taught. (Pilard 2: [0027] – double bond). While Pilard does not use the “olefin cross metathesis catalyst” language in haec verba, Pilard does teach at least Hoveyda-Grubbs catalysts (Pilard 2: [0027]), which the Specification states are “olefin cross metathesis catalysts.” (S. 3: [0030]). Pilard mixes these components into various reactors, versus a screw extruder as claimed. (Pilard 3: [0043] et seq. – Examples). This difference does not impart patentability. Yang (i.e. Applicant ExxonMobil Chemical Patents Inc.) teaches that various extruders are conventional mixing equipment. (Yang 14: [0185]). Use of conventional mixing equipment to mix materials is an obvious expedient. MPEP 2143; KSR.
Claim 11 further requires “mixing the polymeric material and the unsaturated compound in a mixing zone in the screw extruder.” Pilard mixes these components into various reactors, versus a screw extruder as claimed. (Pilard 3: [0043] et seq. – Examples). This difference does not impart patentability. Yang (i.e. Applicant ExxonMobil Chemical Patents Inc.) teaches that various extruders are conventional mixing equipment. (Yang 14: [0185]). Use of conventional mixing equipment to mix materials is an obvious expedient. MPEP 2143; KSR.
Claim 11 further requires “reacting at least a portion of the polymeric material with the unsaturated compound in the presence of the olefin cross metathesis catalyst to produce at least metathesis oil and metathesis carbon black, wherein the metathesis oil comprises an olefin cross metathesis product of the polymeric material and the unsaturated compound.” The materials are so reacted. (Pilard 3: [0054], [0058]).
Claim 11 further requires “separating at least a portion of the metathesis carbon black.” The carbon black is separated. (Pilard 3: [0054]).
As to Claim 12, butadiene rubbers are taught. (Pilard 1: [0004]; 2: [0032]).
As to Claim 13, at least tire material is taught. (Pilard 1: [0004]; 2: [0032]).
As to Claim 14, cis-2-butene-1,4-diacetate has 8 carbons. (Pilard 2: [0027]). As understood, with the double bond, cis-2-butene-1,4-diacetate would have at least one degree of unsaturation.
As to Claim 15, the Hoveyda-Grubbs catalyst is one example of an organomolybdenum, organotungsten, or organoruthenium catalyst according to the Specification. (S. 3: [0030]). Pilard teaches Hoveyda-Grubbs catalysts. (Pilard 2: [0027]).
Allowable Subject Matter
I. Claim 22 is allowed.
US 2012/0323037 to Pilard, et al. was the closest prior art uncovered by the search. Pilard does not teach or reasonably suggest carrying out the specific quantification process claimed in Claim 22.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to DANIEL C. MCCRACKEN whose telephone number is (571) 272-6537. The examiner can normally be reached on Monday-Friday (9-6).
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Anthony J. Zimmer can be reached on 571-270-3591. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/DANIEL C. MCCRACKEN/Primary Examiner, Art Unit 1736
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