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 .
Detailed Action
This office action is in response to applicant’s communication filed on 7/16/26.
Claims 1-20 are pending in this application.
Applicant's election with traverse of Group 1, claims 1-17, in the reply filed on 7/16/26 is acknowledged. The earlier traversal on 10/7/25 is on the ground(s) that there is no serious burden on the examiner to examine all the claims. This is not found persuasive because the claims of the various groups are divergent in subject matter and are drawn to patentably distinct groups.
Claims 18-20 are withdrawn from consideration being drawn to the non-elected invention.
Applicant’s election of the following is acknowledged herewith:
Tire forming additive
As a result, claims 1-17 are being examined in this Office Action.
Objections
Claim 6 is objected to because of the following informalities:
Claims 6 has awkward spacing and indenting.
Claim 6 further recites “2-mercaptobenzothiazole,dibenzothiazyl” without a space and lists “dibenzothiazyl disulfide” and “(2-2′-dithiobis(benzothiazole))” as separate alternatives even though they appear to identify the same compound. The latter also appears to require the locant “2,2′-” rather than “2-2′-.”
Appropriate correction is required.
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.
Claim 4 is rejected under 35 U.S.C. 112(b) as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor regards as the invention.
Claim 4 recites “N,N′-phenol derivatives of 4-aminodiphenylamine.” The specification repeats this phrase in the claim set but does not define it or identify a structural class. It is unclear whether “phenol” is intended to identify a phenolic derivative or is a typographical error for “phenyl”. These readings produce materially different scope. Accordingly, the metes and bounds of claim 4 are not reasonably ascertainable, and appropriate correction or definition is required.
Claim 10 is rejected under 35 U.S.C. 112(b) as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor regards as the invention.
Claim 10 recites “synthesizing the at least one of aniline and the alkyl of the aniline.” The phrase “the alkyl” lacks antecedent basis and does not identify a chemical compound. It is unclear whether the claim intends an alkyl-substituted aniline, an alkyl moiety of an aniline, or another species. These readings produce materially different scope. Accordingly, the metes and bounds of claim 10 are unclear, and 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 is incorrect, any correction of the statutory basis 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 of this title, 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 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 1-7 and 10-11 are rejected under 35 U.S.C. 103 as being unpatentable over Hattori et al. (US 20150315125, published November 5, 2015; hereinafter “Hattori”) in view of Miao et al. (“Selective Synthesis of Benzene, Toluene, and Xylenes from Syngas,” ACS Catalysis 2020, 10, 7389-7397, published May 28, 2020; hereinafter “Miao”, in applicant’s IDS filed 2/29/24).
Determination of the Scope and Content of the Prior Art
(MPEP §2141.01)
Hattori teaches a renewable route to rubber chemicals for tires. Hattori converts biomass-derived ethanol to benzene, converts benzene through nitrobenzene to aniline, converts aniline to anti-degradants and vulcanization accelerators, combines these compounds with additives and rubber polymers, and forms a pneumatic tire. Hattori expressly prepares antioxidants 6PPD, TMDQ, 2-mercaptobenzothiazole, and N-cyclohexyl-2-benzothiazylsulfenamide. (Hattori, paragraphs [0065], [0097]-[0109], [0143]-[0163], and [0274]-[0297])
Miao teaches that nonpetroleum carbon resources, including biomass, can be converted to synthesis gas containing carbon monoxide and hydrogen and that the synthesis gas can be converted directly to benzene, toluene, and xylenes. Miao demonstrates this conversion in a fixed-bed reactor using a metal-oxide/zeolite catalyst system comprising MnCr-ZSM-5 and a second zeolite bed, obtaining a BTX fraction above 80% with beta zeolite and about 88% with USY zeolite. (Miao, Abstract; page 7389, Introduction; page 7390, Sections 2.1 and 2.3)
Ascertainment of the Difference Between the Prior Art and the Claims
(MPEP §2141.02)
Regarding claim 1, Hattori teaches synthesizing benzene, synthesizing aniline from the benzene, and synthesizing from the aniline a tire-forming additive selected from an anti-degradant or vulcanization accelerator. (Hattori, paragraphs [0065], [0097]-[0109], [0143]-[0163])
However, Hattori does not use a biomass-to-syngas route for its benzene.
Miao cures this deficiency by teaching conversion of biomass to syngas and catalytic synthesis of BTX, including benzene, from the carbon monoxide and hydrogen in that syngas. (Miao, Abstract and page 7389)
Regarding claim 2, Hattori identifies p-phenylenediamine and quinoline antioxidants, including 6PPD and TMDQ, as anti-degradants for rubber compositions. (Hattori, paragraphs [0097]-[0100], [0154]-[0159], and [0274]-[0297])
Regarding claim 3, Hattori synthesizes 4-aminodiphenylamine from aniline and then reductively alkylates the 4-aminodiphenylamine to form 6PPD. (Hattori, paragraphs [0155]-[0159])
Regarding claim 4, Hattori discloses N-(1,3-dimethylbutyl)-N′-phenyl-1,4-benzenediamine, i.e., 6PPD, and 2,2,4-trimethyl-1,2-dihydroquinoline polymers, i.e., TMDQ. (Hattori, paragraphs [0098]-[0100], [0154], and [0159])
Regarding claim 5, Hattori teaches thiazole accelerators and sulfenamide accelerators. (Hattori, paragraphs [0108]-[0109] and [0162]-[0163])
Regarding claim 6, Hattori prepares 2-mercaptobenzothiazole and N-cyclohexyl-2-benzothiazylsulfenamide and also identifies dibenzothiazyl disulfide, N,N′-dicyclohexyl-2-benzothiazylsulfenamide, and N-tert-butyl-2-benzothiazylsulfenamide. (Hattori, paragraphs [0108]-[0109] and [0162]-[0163])
Regarding claims 7 and 11, Miao performs the synthesis-gas-to-aromatics conversion with ZSM-5 and a second bed selected from beta, USY, mordenite, ZSM-5, or SAPO-34. Thus, the catalyst system comprises a zeolite-based catalyst. (Miao, Abstract; page 7390, Sections 2.1 and 2.3)
Regarding claim 10, Hattori expressly nitrates benzene to nitrobenzene and reduces the nitrobenzene to aniline. (Hattori, paragraphs [0065] and [0146])
Finding of Prima Facie Obviousness Rationale and Motivation
(MPEP §2142-2143)
Therefore, it would have been prima facie obvious to one of ordinary skill in the art before the effective filing date to modify Hattori by obtaining its benzene intermediate through Miao’s biomass-to-syngas-to-BTX route. Hattori seeks nonpetroleum routes to the same benzene intermediate, and Miao identifies biomass-derived syngas as an alternative source of BTX. The modification substitutes a known source of chemically identical benzene for Hattori’s bioethanol-derived benzene. (Hattori, paragraphs [0003]-[0010] and [0065]; Miao, page 7389, Introduction; MPEP §2143(I)(B))
One of ordinary skill would have had a reasonable expectation of success because Miao experimentally produces BTX from synthesis gas and reports stable operation through 100 hours, while Hattori uses conventional benzene-to-aniline and aniline-to-rubber-chemical reactions. Because the proposed modification changes the source of the benzene intermediate rather than its chemical identity, those downstream reactions would operate predictably. (Miao, pages 7390 and 7394; Hattori, paragraphs [0065] and [0143]-[0163])
Claim 8 is rejected under 35 U.S.C. 103 as being unpatentable over Hattori in view of Miao as applied to claim 7 above, and further in view of Brosius and Claeys (“Aromatics from Syngas: CO Taking Control,” Chem 3, 202-204, August 10, 2017; hereinafter “Brosius”, in applicant’s IDS filed 2/29/24).
Determination of the Scope and Content of the Prior Art
(MPEP §2141.01)
Hattori and Miao teach the subject matter of claim 7 as discussed above.
Brosius teaches direct conversion of synthesis gas containing carbon monoxide and hydrogen to aromatics with a bifunctional catalyst composed of Zn-ZrO2 nanoparticles and H-ZSM-5 zeolite. Brosius reports that the catalyst remains stable and that proximity of the zeolite and Zn-ZrO2 particles is important. (Brosius, pages 202-203)
Ascertainment of the Difference Between the Prior Art and the Claim
(MPEP §2141.02)
Miao’s working dual-bed catalyst satisfies claim 7 but uses a MnCr oxide component rather than requiring zinc. Brosius expressly supplies the further zinc-based catalyst required by claim 8 in the same type of zeolite-containing synthesis-gas-to-aromatics system. (Miao, pages 7389-7390; Brosius, page 203)
Finding of Prima Facie Obviousness Rationale and Motivation
(MPEP §2142-2143)
Thus, it would have been prima facie obvious to use Brosius’s Zn-ZrO2/H-ZSM-5 catalyst system as a known zinc-containing alternative in Miao’s direct synthesis of aromatics from syngas. Both systems combine a metal oxide with a zeolite for the same conversion, and Brosius reports stable operation. The substitution therefore applies a known catalyst system to its known function with a reasonable expectation of producing BTX, which includes benzene.
Claims 9 and 12-15 are rejected under 35 U.S.C. 103 as being unpatentable over Hattori in view of Miao as applied to claim 1 above, and further in view of Eilos et al. (US 20130005838, published January 3, 2013; hereinafter “Eilos”).
Determination of the Scope and Content of the Prior Art
(MPEP §2141.01)
Hattori and Miao teach the subject matter of claim 1 as discussed above. Miao also states that approximately 70% of the BTX supply is produced by reforming naphtha. (Miao, page 7389, Introduction)
Eilos teaches gasifying biomass to syngas, adjusting the H2/CO ratio by a water-gas shift reaction, and converting the adjusted carbon monoxide and hydrogen by Fischer-Tropsch synthesis to C4-C90 hydrocarbons that include naphtha. Eilos identifies removal of sulfur before water-gas shift, separation of ash from syngas by filtering, and biomass sources including wood chips and yard clippings. (Eilos, paragraphs [0003]-[0006], [0010]-[0011], [0022]-[0024], [0041]-[0042], and [0106])
Ascertainment of the Difference Between the Prior Art and the Claims
(MPEP §2141.02)
Regarding claim 9, Hattori and Miao do not exemplify the Fischer-Tropsch-to-naphtha step. Eilos supplies conversion of syngas carbon monoxide and hydrogen to Fischer-Tropsch products expressly including naphtha, while Miao identifies catalytic reforming of naphtha as the predominant established source of BTX. The combined sequence therefore converts syngas to naphtha and reforms the naphtha to obtain the benzene used by Hattori. (Eilos, paragraphs [0041]-[0042]; Miao, page 7389, Introduction)
Regarding claim 12, Eilos modifies the H2/CO molar ratio of biomass-derived syngas by converting carbon monoxide and steam to carbon dioxide and hydrogen in a water-gas shift reaction and controls the product-gas ratio by bypassing part of the gas around the shift reactor. (Eilos, paragraphs [0004], [0010], and [0106])
Regarding claim 13, Eilos teaches reducing sulfur content by removing sulfur from the feed gas before the water-gas shift process. (Eilos, paragraph [0006])
Regarding claim 14, Eilos teaches that inorganic matter from biomass gasification forms ash particles and that the ash is separated from syngas by filtering. (Eilos, paragraph [0024])
Regarding claim 15, Eilos identifies wood chips, as biomass for a biomass-to-liquids process. Eilos also identifies yard clippings, corresponding to the recited yard wastes. (Eilos, paragraph [0022])
Finding of Prima Facie Obviousness Rationale and Motivation
(MPEP §2142-2143)
Thus it would have been prima facie obvious to use Eilos’s known biomass-syngas conditioning and Fischer-Tropsch steps in the Hattori-Miao process. Eilos teaches that H2/CO adjustment prepares syngas for downstream synthesis, and that sulfur and ash are impurities that may be removed before catalytic processing. These are predictable feed-conditioning measures for preparing the synthesis gas supplied to Miao’s catalytic aromatic synthesis. (Eilos, paragraphs [0003]-[0015], [0024], and [0106])
It also would have been obvious to select Eilos’s Fischer-Tropsch naphtha as an alternative intermediate and reform it by the conventional route identified by Miao to obtain the benzene required by Hattori. Eilos expressly produces naphtha from syngas, and Miao identifies naphtha reforming as the predominant established route to aromatics; the combination therefore uses each process for its known function with a reasonable expectation of obtaining benzene. (Eilos, paragraphs [0041]-[0042]; Miao, page 7389)
Claim 16 is rejected under 35 U.S.C. 103 as being unpatentable over Hattori in view of Miao as applied to claim 1 above, and further in view of Lynch et al. (US 20130178671, published July 11, 2013; hereinafter “Lynch”).
Determination of the Scope and Content of the Prior Art
(MPEP §2141.01)
Hattori and Miao teach the subject matter of claim 1 as discussed above. Hattori also converts ethanol to ethylene and styrene, converts ethanol to 1,3-butadiene, polymerizes styrene and butadiene to styrene butadiene rubber (SBR), and combines SBR, butadiene rubber (BR), or natural rubber with the claimed tire-forming additives in a tire composition. (Hattori, paragraphs [0164]-[0181] and [0274]-[0297])
Lynch teaches producing ethanol from synthesis gas containing hydrogen and carbon monoxide. The process converts the synthesis gas through methanol and an ether and then uses carbonylation and hydrogenolysis to recover ethanol. (Lynch, Abstract; paragraphs [0002]-[0005]; claim 1)
Ascertainment of the Difference Between the Prior Art and the Claim
(MPEP §2141.02)
Hattori makes and combines the rubber polymer with the tire-forming additive, but it begins with bioethanol rather than producing that ethanol from the syngas of claim 1.
Lynch cures the deficiency by producing ethanol from carbon monoxide and hydrogen in syngas. Feeding Lynch’s syngas-derived ethanol to Hattori’s ethanol-to-styrene, ethanol-to-butadiene, and polymerization steps synthesizes SBR or BR from syngas and combines the rubber polymer with Hattori’s tire-forming additive. (Lynch, Abstract; paragraphs [0002]-[0005]; claim 1)
Finding of Prima Facie Obviousness Rationale and Motivation
(MPEP §2142-2143)
Thus, it would have been prima facie obvious to supply Hattori’s ethanol-based synthetic-rubber route with Lynch’s syngas-derived ethanol. Hattori seeks non-petroleum sources for tire chemicals and rubber, Miao supplies biomass-derived syngas, and Lynch supplies the same ethanol intermediate from carbon monoxide and hydrogen in syngas. The modification substitutes a known source of chemically identical ethanol and predictably yields Hattori’s SBR or BR for combination with the tire additive.
Claim 17 is rejected under 35 U.S.C. 103 as being unpatentable over Hattori in view of Miao as applied to claim 1 above, and further in view of Kriegel et al. (US 20090246430, published October 1, 2009; hereinafter “Kriegel”) and Chung et al. (US 20140299246, published October 9, 2014; hereinafter “Chung”).
Determination of the Scope and Content of the Prior Art
(MPEP §2141.01)
Hattori and Miao teach the subject matter of claim 1 as discussed above. Hattori further teaches a rubber composition containing the aniline-derived tire-forming additive and a rubber-forming polymer, including SBR, BR, or natural rubber. (Hattori, paragraphs [0274]-[0297])
Kriegel teaches making bio-based polyethylene terephthalate (PET) by reacting ethylene glycol with terephthalic acid. Kriegel expressly teaches gasifying bio-based material to syngas, converting the syngas to ethanol, converting ethanol through ethylene and ethylene oxide to ethylene glycol, and separately converting syngas to p-xylene and oxidizing p-xylene to terephthalic acid. Thus, Kriegel teaches the reaction of syngas to produce both PET precursors and then to PET. (Kriegel, paragraphs [0020], [0022], and [0025])
Chung teaches that PET fiber cords reinforce rubber and form part of a tire’s skeletal structure. Chung prepares PET tire cord, uses it as a cap ply or body ply, and provides a pneumatic tire including the PET tire cord. (Chung, paragraphs [0012]-[0016], [0038], and [0084]-[0086]; claims 3, 5, 11, and 17)
Ascertainment of the Difference Between the Prior Art and the Claim
(MPEP §2141.02)
Hattori supplies the rubber composition derived from the tire-forming additive and rubber-forming polymer, but Hattori and Miao do not expressly synthesize a reinforcing material from syngas and combine it with that composition. Kriegel cures the syngas-source deficiency by synthesizing PET from syngas-derived ethylene glycol and terephthalic acid. Chung cures the end-use problem by forming that PET into tire cord that reinforces the rubber of a pneumatic tire. The combination therefore supplies the reinforcing material, its synthesis from syngas, and its combination with Hattori’s additive-containing rubber composition. (Kriegel, paragraphs [0020], [0022], and [0025]; Chung, paragraphs [0014]-[0016], [0038], and [0084]-[0086])
Finding of Prima Facie Obviousness Rationale and Motivation
(MPEP §2142-2143)
Thus, it would have been prima facie obvious to form Kriegel’s syngas-derived PET into Chung’s known PET tire cord and use the cord to reinforce Hattori’s tire composition. Kriegel provides renewable PET that is intended to share the properties and processing of petroleum-derived PET, Chung identifies PET cord as a known tire reinforcement, and Hattori seeks to reduce petroleum use in tire materials. The proposed use applies each known material and process according to its established function and predictably increases renewable content while retaining PET cord reinforcement. (Kriegel, paragraphs [0005]-[0006], [0020], [0022], and [0025])
Double Patenting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy 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. See 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); and In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting when the reference application or patent is shown to be commonly owned with the examined application. A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b). Filing a terminal disclaimer alone is not a complete reply; the reply must also request reconsideration of the Office action. (37 CFR 1.321(b) and (c); MPEP §804, subsection I.B.1)
Claims 1-3, 7-9, 11-14, and 16-17 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-3, 7-9, 11, 13-14, and 16-17 of copending Application No. 17936112 in view of Eilos et al. (US 2013/0005838 A1, published January 3, 2013; hereinafter “Eilos”).
Claims 4 and 10 are not included in the provisional nonstatutory double patenting rejections because those claims are separately rejected under 35 U.S.C. 112(b) as being indefinite.
Although the claims at issue are not identical, they are not patentably distinct. Current claim 1 of the copending application converts shredded tires or rubber-containing components to syngas, adjusts the H2/CO ratio, converts the conditioned syngas to benzene or an alkyl benzene, converts the aromatic to aniline or an alkyl aniline, and forms the same class of tire additive in a sequential reactor system.
Eilos teaches gasifying biomass to the same carbon-monoxide-and-hydrogen syngas. It would have been obvious to substitute Eilos’s biomass for the shredded-tire feed because each is a known carbonaceous feed that supplies syngas for downstream synthesis. (Eilos, paragraphs [0003] and [0011])
Instant claims 2-3, 7-9, 11, 13-14, and 16-17 recite the same dependent limitations found in current copending claims 2-3, 7-9, 11, 13-14, and 16-17. Instant claim 12 is met by the H2/CO adjustment already required by current copending claim 1.
Claims 5 and 6 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claim 1 of copending Application No. 17936112 in view of Eilos et al. (US 20130005838, published January 3, 2013; hereinafter “Eilos”) and Hattori et al. (US 20150315125, published November 5, 2015; hereinafter “Hattori”).
As explained above, copending claim 1 in view of Eilos renders the biomass-based method of instant claim 1 an obvious variation.
Copending claim 1 allows for a vulcanization accelerator as the tire-forming additive. Hattori teaches the known thiazole and sulfenamide accelerators recited in instant claims 5 and 6, including 2-mercaptobenzothiazole and N-cyclohexyl-2-benzothiazylsulfenamide. Selecting those known tire accelerators for the permitted accelerator would have been obvious. (Hattori, paragraphs [0108]-[0109] and [0162]-[0163])
Claim 15 is provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claim 1 of copending Application No. 17936112 in view of Eilos et al. (US 20130005838, published January 3, 2013; hereinafter “Eilos”).
Eilos identifies wood chips and yard clippings as biomass-to-liquids feedstocks. Selecting either disclosed biomass feed for the biomass-for-shredded-tire substitution discussed above would have been obvious. (Eilos, paragraphs [0003], [0011], and [0022])
These are provisional nonstatutory double patenting rejections because the patentably indistinct claims have not in fact been patented.
Conclusion
No claim is allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Jennifer Cho Sawyer whose telephone number is (571) 270 1690. The examiner can normally be reached on Monday-Friday 9 AM - 6 PM PST.
If attempts to reach the examiner by telephone are unsuccessful, the examiner's supervisor, Renee Claytor can be reached on (571) 272-8394. The fax phone number for the organization where this application or proceeding is assigned is 571-274-1690.
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Jennifer Cho Sawyer
Patent Examiner
Art Unit: 1691
/RENEE CLAYTOR/Supervisory Patent Examiner, Art Unit 1691
Prosecution Insights