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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 8/12/2026 has been entered.
Election/Restrictions
Claim 7 is withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on 1/29/2025.
Response to Amendment
The amendment of claims filed on 8/12/2026 has been entered. Claim(s) 1 and 3 is/are currently amended. Claim(s) 1-19 is/are pending with claim(s) 7 withdrawn from consideration. Claim(s) 1-6 and 8-19 is/are under examination in this office action.
Response to Arguments
Applicant's argument filed on 8/12/2026, with respect to 112(b) rejection has been fully considered and is persuasive. The 112(b) rejection is withdrawn.
Applicant's argument filed on 8/12/2026, with respect to 103 rejection has been fully considered but is not persuasive.
Applicant argued that the amended claim 1 now requires R4 = C4H9O (2-ethoxyethyl or 3-methoxypropyl) or C5H11O (3-ethoxypropyl). The closest R4 group in Carbajal is C3H7O (2-methoxyethyl). Importantly, the Examiner's own analysis in the Advisory Action acknowledged that methoxymethyl acrylate (from the now-deleted C2H5O group) "should have log P and HE values closer to 2-methoxyethyl acrylate than 2-ethoxyethyl acrylate and 3-ethoxypropyl acrylate." By removing C2H5O, the claims are now directed exclusively to R4 groups that the Examiner's own reasoning recognizes as having significantly different molecular properties from Carbajal's monomer. The Specification data confirms these differences. As shown in the Specification, the monomer-level molecular parameters for the remaining claimed monomers differ substantially from 2-methoxyethyl acrylate (2MEA).
In response, applicant needs to provide practical data for these acrylates in demulsification performance, and show that 2-methoxyethyl acrylate has different demulsification performance from 2-ethoxyethyl acrylate and 3-ethoxypropyl acrylate. Difference in log P and HE in a comonomer unit cannot lead to the conclusion that the demulsification performance of the copolymer will be different.
Applicant argued that homolog presumption is rebutted because structural similarity is overcome where there is evidence showing there is no reasonable expectation of similar properties in structurally similar compounds; and homologs that are "far removed from adjacent homologs may not be expected to have similar properties.
In response, applicant did not provide evidence to show different demulsification performance from 2-ethoxyethyl acrylate and 3-ethoxypropyl acrylate.
Applicant argued that the Specification's experimental data demonstrates that this structural difference results in fundamentally different performance. The Bipolymer_37_2MEA (using Carbajal's 2- methoxyethyl monomer) showed ZERO efficiency in removing emulsified water - it actually acted as a surfactant that further stabilized the emulsion. In contrast, the bipolymers using the claimed monomers (KE_2EEA with 2-ethoxyethyl and KE_2EPA with 3-ethoxypropyl) achieved 100% and 92% water removal efficiency, respectively.
In response, the examiner did not find the above experimental data in the originally filed specification. Applicant provided the experimental data in the 3/18/2026 argument; and the argument was addressed in the response of 4/20/2026 office action. It should be pointed out that when any claim of an application or a patent under reexamination is rejected or objected to, any evidence submitted to traverse the rejection or objection on a basis not otherwise provided for must be by way of an oath or declaration (MPEP 716). The applicant did not provide a declaration to show the experimental data. Therefore, the recited experimental data cannot be relied upon to traverse the rejection.
Applicant argued that the amended claim 1 now recites molecular masses from 800 to 6,000 g mol-1. Carbajal teaches molecular weights of preferably 7,000 to 120,000 Daltons ( [0087]). The claimed range of 800-6,000 falls entirely below Carbajal's preferred molecular weight range. Even Carbajal's broader range of 1,000 to 180,000 Daltons has its lower bound at 1,000. The claimed range of 800-6,000 extends below Carbajal's lower bound and does not encompass any of Carbajal's preferred molecular weight range.
In response, Carbajal's molecular weight range of 1,000 to 180,000 Daltons overlaps the claimed range of 800-6,000. A prima facie case of obviousness exists where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" (MPEP 2144.05.I).
Applicant argued that this molecular mass narrowing represents a meaningful structural distinction. The molecular mass of a copolymer directly affects its physical properties, including its ability to diffuse through crude oil, interact with water/oil interfaces, and function as a demulsifier. Lower molecular mass bipolymers occupy a fundamentally different portion of the structural space than the higher molecular weight copolymers preferred by Carbajal for defoaming.
In response, arguments presented by the applicant cannot take the place of evidence in the record. In re Schulze, 346 F.2d 600, 602, 145 USPQ 716, 718 (CCPA 1965), MPEP 716.01(c).
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 text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
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) 1-6, 8-10, 12-15, and 17-19 is/are rejected under 35 U.S.C. 103 as being unpatentable over Carbajal et al (US 20170015897 A1).
Regarding claims 1-4, Carbajal teaches a method for defoaming crude oil by the addition of copolymers based on silicone free alkyl acrylics defoamers for crude oils [abstract]. The copolymers have the formula (1):
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where R1 and R3═ hydrogen or methyl; R2 and R4═ methyl, ethyl, n-butyl, isobutyl, n-hexyl, iso-hexyl, 2 ethyl-hexyl, n-octyl, n-decyl, iso-decyl, n-dodecyl, n-octadecyl, 2-methoxyethyl, 2-(2-methoxyethoxy)ethyl; this aliphatic chain may contain heteroatoms of the ether group, aromatic rings or rings with heteroatoms of ether type; x=is a number preferably between 20 and 850; y=is a number preferably between 20 and 850, and “x” and “y” vary randomly along the copolymer chain [0054-0060]. The monomers can be used in a monomer weight ratio of 70/30 [0061]. The molecular weights of the copolymers range from 1,000 to 180,000 Daltons [0087].
It would have been obvious to one of ordinary skill in the art at the time of filing to select R1 and R3═ hydrogen or methyl; R2 = methyl, ethyl, n-butyl, isobutyl, n-hexyl, iso-hexyl, n-decyl, iso-decyl, n-dodecyl, n-octadecyl; and R4 = 2-methoxyethyl in Carbajal’s composition, as these are expressly disclosed as being useful in this capacity. It has been established that selection of a known material based on its suitability for its intended use is prima facie obvious (Sinclair & Carroll Co. v. Interchemical Corp., 325 U.S. 327, 65 USPQ 297 (1945)). See MPEP 2144.07.
The examiner submits that Carbajal’s R1, R2, and R3 overlap the claimed R1, R2, and R3 as defined in claims 1-3.
Carbajal teaches 2-methoxyethyl (C3H7O) as the R4 group [0057] but does not teach ethoxyethyl (C4H9O) , 3-methoxypropyl (C4H9O) or 3-ethoxypropyl (C5H11O). However, ethoxyethyl, 3-ethoxypropyl, 3-methoxypropyl and methoxyethyl are homologs - compounds differing regularly by the successive addition of the same chemical groups, in the present instance, a CH2 group. Homologs “are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties”. In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977), MPEP 2144.09.II. Additionally, Carbajal describes the same utility of methoxyethyl as the claimed ethoxyethyl and 3-ethoxypropyl: the R4 group in the copolymer.
A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. "An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties." In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979); MPEP 2144.09.
It would have been obvious to one of ordinary skill in the art at the time of the invention to modify Carbajal to select 2-ethoxyethyl, 3-methoxypropyl or 3-ethoxypropyl as a homolog of methoxyethyl, as ethoxyethyl and 3-ethoxypropyl are expected to possess similar properties and have similar utility as methoxyethyl.
Carbajal’s x and y falls within the claimed ranges of x and y in claim 1; Carbajal’s monomer weight ratio of 70/30 falls within the claimed range of about 55 to about 99% by weight of the alkyl acrylate and about 1 to about 45% by weight of the alkoxy alkyl acrylate recited in claim 4; Carbajal’s molecular weight of 1,000 to 180,000 Daltons overlaps the recited range of 800-6,000 g/mol. A prima facie case of obviousness exists where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" (MPEP 2144.05.I). The copolymer is a random biopolymer because it contains two monomer units x and y which vary randomly along the copolymer chain.
The preamble of “demulsifier agent for removing emulsified water in crude oil” represents a statement of intended use that imparts no additional structure beyond the claimed formula (1) and need not be taught by the prior art to read on the claimed invention. See MPEP 2111.02(III).
The recited “wherein the demulsifier agent has a Partition coefficient (Log P) ranging from 6.00 to 200.00, a Hydration Energy (kcal/mol) ranging from -1.00 to -110.00, a Molecular refractivity (A3) ranging from 250.00 to 20,000.00, and a Polarizability (A3) from 100.00 to 2,000.00” is a new matter as stated in the 112(a) rejection. Besides, the recited limitation is properties of the product. “Products of identical chemical composition cannot have mutually exclusive properties." A chemical composition and its properties are inseparable. Therefore, if the prior art teaches the identical chemical structure, the properties applicant discloses and/or claims are necessarily present. In re Spada, 911 F.2d 705, 709, 15 USPQ2d 1655, 1658 (Fed. Cir. 1990)). See MPEP 2112.01. Since Carbajal teaches the same product, the recited properties are expected to be present.
Regarding claim 5, Carbajal teaches that the amount of copolymer in the resulting solution and formulation is preferably between 20 and 40 wt % [0078], falling within the claimed range of about 3 to about 60 wt%.
Regarding claim 6, Carbajal teaches that the solvents have a boiling point in the range from 35 to 200°C [0117], falling within the claimed range of about 30-250 °C.
Regarding claims 8, 9, 12, 14, 15, Carbajal teaches that R2 can be n-butyl, isobutyl, 2-ethyl-hexyl, and n-octyl, 2-phenoxyethyl (ethylene glycol phenyl ether), n-decyl, iso-decyl, n-dodecyl, n-octadecyl, as stated above.
Regarding claim 10, Carbajal teaches 3,5,5-trimethylhexyl acrylate as the monomer candidate [0062].
Regarding claim 13, Carbajal teaches 4-tert-butylcyclohexyl acrylate as the monomer candidate [0088].
Regarding claims 17-18, it would have been obvious to one of ordinary skill in the art at the time of the invention to modify Carbajal to select ethoxyethyl, 3-methoxypropyl or 3-ethoxypropyl, as stated above.
Regarding claim 19, Carbajal teaches 2-(2-methoxyethoxy )ethyl as the R4 [0057].
Claim(s) 11 and 16 is/are rejected under 35 U.S.C. 103 as being unpatentable over Carbajal as applied to claim 1 above, further in view of Behles (US 20070244248 A1).
Regarding claim 11, Carbajal teaches the demulsifier agent in claim 1. Carbajal does not teach R2 is C8H9. However, Carbajal taches that the aliphatic chain may contain aromatic rings [0057].
In the same field of endeavor, Behles teaches a copolymer as demulsifier for crude oil treatment [abstract, 0002, 0005] comprising monomer unit of 2-phenylethyl(meth)acrylate [0017].
It would have been obvious to one of ordinary skill in the art at the time of filing to use 2-phenylethyl(meth)acrylate as a monomer unit in Carbajal’s copolymer, as it is expressly disclosed as being useful in this capacity. It has been established that selection of a known material based on its suitability for its intended use is prima facie obvious (Sinclair & Carroll Co. v. Interchemical Corp., 325 U.S. 327, 65 USPQ 297 (1945)). See MPEP 2144.07.
The 2-phenylethyl group reads on the claimed C8H9.
Regarding claim 16, Carbajal teaches the demulsifier agent in claim 1. Carbajal does not teach R2 is in a form selected from the group consisting of tetrahydrofurfuryl and 2-tetrahydropyranyl. However, Carbajal taches that the aliphatic chain may contain heteroatoms of the ether group [0057].
In the same field of endeavor, Behles teaches a copolymer as demulsifier for crude oil treatment [abstract, 0002, 0005] comprising monomer unit of tetrahydrofurfuryl (meth)acrylate [0017].
It would have been obvious to one of ordinary skill in the art at the time of filing to use tetrahydrofurfuryl (meth)acrylate as a monomer unit in Carbajal’s copolymer, as it is expressly disclosed as being useful in this capacity. It has been established that selection of a known material based on its suitability for its intended use is prima facie obvious (Sinclair & Carroll Co. v. Interchemical Corp., 325 U.S. 327, 65 USPQ 297 (1945)). See MPEP 2144.07.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to JIANGTIAN XU whose telephone number is (571)270-1621. The examiner can normally be reached Monday-Thursday.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Robert Jones can be reached on (571) 270-7733. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/JIANGTIAN XU/Primary Examiner, Art Unit 1762
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