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 .
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 02/06/2026 has been entered.
Status of the Claims
The amendment filed on 02/06/2026 has been entered. Claim 1 has been amended. Thus claims 1-4, 8, 11-13, 15, 17, 20-21, 28-31, 39-40 and 43 are currently pending; claim 8 has been withdrawn from further consideration; and claims 1-4, 11-13, 15, 17, 20-21, 28-31, 39-40 and 43 are under examination.
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.
Claims 1-4, 11-13, 15, 17, 20-21, 28-31, 39-40 and 43 are rejected under 35 U.S.C. 103 as being unpatentable over Patent number US6,049,011 (US’011; cited in PTO-892 06/16/2025) in view of Patent number EP0713906A1 (EP’905; original and machine translation cited in PTO-895 01/28/2026). See underlined for the modification.
Regarding claims 1-4, US’011 teaches a method of making propionaldehyde comprising hydroformylating a feed stream source comprising ethylene (columns 9-10). The reference further teaches that the feed stream source is obtained from cracking operations of hydrocarbon (equivalent to non-recyclable hydrocarbons), the hydrocarbon being selected from light hydrocarbon gases through light liquid to heavy liquid hydrocarbons, e.g., vacuum gas oil, and the cracking being, for example, catalytic, thermal or steam cracking, or hydrocracking (columns 3-5). Furthermore, the process of the reference does not subject the non-recycle hydrocarbon to hydrogenation before and during steam cracking
Regarding claims 1-4 and 7, while US’011 teaches obtaining propionaldehyde by first steam cracking non-recycle hydrocarbons to stream comprising ethylene followed by hydroformylating the stream to propionaldehyde, the reference fails to teach that the ethylene used is a recycle ethylene composition (r-ethylene) and the method for making r-pyoil followed by cracking r-pyoil (claim 1), and the method for obtaining an ethylene composition designated as having recycle content (claim 2).
However, the deficiencies are cured by EP’906.
EP’906 teaches a method for obtaining a recycle ethylene by pyrolyzing a plastic wate feedstock to produce naphtha oil/ gas oils (r-pyoil), followed by steam cracking to obtain a composition comprising ethylene (r-ethylene) ([0002], [0010]-[0012]).
The reference teaches the plastic waste contains approximately 70% by weight of polyolefins such as polyethylene and polypropylene, approximately 15% by weight of styrene polymers, approximately 10% by weight of PVC and in small minor amounts of approximately 5% by weight from other plastics such as polyurethane, polyester and polyamide ([0005]). EP’906 further teaches the pyrolysis is conducted at a temperature of 370 to 550 ° C. ([0011]). In view of MPEP § 2144.05, a prima facie case of obviousness exists where the claimed ranges or amounts do not overlap with the prior art but are merely close. In this instance, the claimed PVC amount in the plastic of not more than 5 wt% and pyrolysis temperature of 600 °C to 1100 °C are merely close to the PVC amount and pyrolysis temperature of EP’906 and thus are prima facie obvious absent any showing of unexpected results or criticality. In fact, the instant specification discloses a broader range in PVC amount ([0133]) and pyrolysis temperature ([0145]) which include the PVC amount and pyrolysis temperature described by EP’906:
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Nowhere in the above disclosure or in any embodiment of the instant specification describes or provides criticality or unexpected result by using the specific PVC amount and pyrolysis temperature as claimed. Instead, the broader PVC amount and pyrolysis temperature that also include the PVC amount and pyrolysis temperature of EP’906, are described as having an equal effect as the narrower claimed ranges in pyrolyzing the plastic waste. As such, the claimed PVC amount and pyrolysis temperature are prima facie obvious over the prior art.
Accordingly, combining non-recycle hydrocarbon of US’011 with r-pyoil of EP’906 at any amount, including the claimed amount of at least 5 wt% and no more than 40 wt% based on the total amount of non-recycle hydrocarbon and r-pyoil (equivalent to the cracker stream) and applying the combined stream to steam cracking, a skilled artisan would still have a reasonable expectation of success in obtaining an effluent comprising r-ethylene. Furthermore, subjecting the effluent comprising r-ethylene to the hydroformylating process of US’011, a skilled artisan would have a reasonable expectation of success in obtaining propionaldehyde.
In accordance to MPEP § 2143, the Supreme Court in KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 415-421, 82 USPQ2d 1385, 1395-97 (2007) identified a number of rationales to support a conclusion of obviousness which are consistent with the proper “functional approach” to the determination of obviousness as laid down in Graham and discussed circumstances in which a patent might be determined to be obvious. In this case, at least prong (A) combining prior art elements according to known methods to yield predictable results.
As such, combining the ethylene of US’011 and r-ethylene of EP’906 and conducting the hydroformylation reaction of US’011 would yield nothing more than the predictable propionaldehyde product.
Regarding claims 11-13, the limitation “wherein said r-ethylene is directly or indirectly from …” is a product by process claim language as a result of r-ethylene. The product by process limitation is not limited to the manipulations of the recited steps for preparing r-ethylene, but only to the structure implied by the steps, in this case, only to r-ethylene. See MPEP § 2113:
"[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. Hoffman-La Roche Ltd., 580 F.3d 1340, 1370 n 14, 92 USPQ2d 1289, 1312, n 14 (Fed. Cir. 2009). See also 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" ).
Furthermore, because the process steps do not appear to impart distinctive structural characteristic to the final r-ethylene, the process steps are not given patentable weight. See MPEP § 2113:
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").
Regarding claims 15 and 17, the reference that teaches the production of r-pyoil, EP’906, is silent that r-pyoil comprises: C4-C12 aliphatic compounds and C13-C22 aliphatic compounds in a weight ratio of at least 1.25:1 by weight and based on the weight of the r-pyoil (claim 15); aliphatic hydrocarbons and the aliphatic hydrocarbons having the highest concentration in the r-pyoil are in a range of C14 (claim 17); not more than 30 weight percent of aromatics, based on the total weight of the r-pyoil (claim 20); olefins present in an amount ranging from 40-85 wt.% based on the weight of the r- pyoil (claim 21); paraffin and napthene, and wherein the weight ratio of paraffin and naphthene combined to aromatics in the r-pyoil can be in a range of from 1:1-7:1 (claim 28); and has a 90% boiling point of the cracker feed stream or composition to a cracker furnace is not more than 350 °C (claim 29). However, since the reference every limitation as claimed in obtaining r-pyoil, there is a prima facie case of anticipation for the r-pyoil of EP’906 to comprise C4-C12 aliphatic compounds and C13-C22 aliphatic compounds in a weight ratio of at least 1.25:1 by weight and based on the weight of the r-pyoil; aliphatic hydrocarbons and the aliphatic hydrocarbons having the highest concentration in the r-pyoil are in a range of C14; not more than 30 weight percent of aromatics, based on the total weight of the r-pyoil; olefins present in an amount ranging from 40-85 wt.% based on the weight of the r- pyoil; paraffin and napthene, and wherein the weight ratio of paraffin and naphthene combined to aromatics in the r-pyoil can be in a range of from 1:1-7:1; and to have a 90% boiling point of the cracker feed stream or composition to a cracker furnace is not more than 350 °C. See MPEP § 2112.01.
Regarding claims 30 and 31, EP’906 teaches feeding a cracker feed stream to a furnace comprising r-pyoil, said cracker feed stream comprising C1 to C4 hydrocarbon containing composition (feedstock B in Table 2 and [0033], [0039]). Furthermore, the reference teaches the cracking is performed by a cracking furnace 6 having a gas coil that receives C1-C4 feedstock, to the inlet of the coil in the convection section (Figures).
Regarding claims 39-40, EP’906 teaches that the crackers include a cracking furnace, gas and liquid separations units and an aromatics separation unit (see Figures 1-2, separation/purification units 7, 12, 10 and 20). Thus, a skilled artisan would have been motivated to connect the cracking facility with the propionaldehyde production unit through the gas and liquid separations units and aromatics separation units.
Regarding claim 43, EP’906 is silent about the r-ethylene containing at least one impurity as instantly claimed. However, since the reference teaches the same r-ethylene derived from cracking r-pyoil as instantly claimed, it is anticipated for the r-ethylene of US’609 to contain at least one impurity as instantly claimed. See MPEP § 2112.01.
It would thus have been prima facie obvious to a skilled artisan before the effective filing date of the instant invention to conduct a method of making recycle propionaldehyde (r-propionaldehyde), said method comprising the steps (i) preparing a recycle pyoil composition (r-pyoil) by pyrolysis of a recycled waste stream comprising at least 30 wt% waste plastic, wherein the waste plastic comprises not more than 5 wt% of polyvinyl chloride and/or polyethylene terephthalate and wherein the pyrolysis temperature is from 600 °C to 1100 °C, to thereby provide said r-pyoil, and thereafter (ii) steam cracking a cracker feed stream composition comprising (a) said r-pyoil in combination with (b) a non-recycle hydrocarbon feed stream, wherein the r-pyoil and the non-recycle hydrocarbon at not subjected to hydrogenation before and during steam cracking; wherein the r- pyoil is present in the cracker feed stream in an amount of at least 5 wt% and no more than 40 wt% based on the total weight of the cracker feed stream composition, to provide an olefin effluent comprising r-ethylene, and thereafter (iii) hydroformylating said r-ethylene to provide said r-propionaldehyde in view of the combination of US’011 and EP’906.
Response to Arguments
Applicant’s arguments with respect to the newly introduced limitation have been addressed in the above modified rejection (see the underlined).
Conclusion
Claims 1-4, 11-13, 15, 17, 20-21, 28-31, 39-40 and 43 are rejected and no claims are allowed.
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/MEDHANIT W BAHTA/Primary Examiner, Art Unit 1692