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 .
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Claim 7 is withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim.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 3/18/2026 has been entered. Claim(s) 1 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 Claim(s) 1-19 is/are pending with claim(s) 7 withdrawn from consideration.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.
The amendment of specification filed on 3/18/2026 has been entered.
Response to Arguments
Applicant's argument filed on 3/18/2026, with respect to objection of specification has been fully considered and is persuasive. The objection of specification is withdrawn.
Applicant's argument filed on 3/18/2026, with respect to 112(a) rejection has been fully considered and is persuasive. The 112(a) rejection is withdrawn.
Applicant's argument filed on 3/18/2026, with respect to 103 rejection has been fully considered but is not persuasive.
Applicant argued that the bipolymer B_37_2MEA displays the lowest Log P value, which implies the lowest capability to diffuse through crude oil. Besides, this bipolymer shows the highest negative HE value. Thus, it presents a high capability to form hydrogen bonds. The three bipolymers were assessed in the TMDB crude oil at a dosage of 1000 ppm. As can be observed, only the KE_2EEA and KE_2EPA bipolymers were able to induce the destabilization of the water/crude oil interphase and thus, to induce the coalescence of the water droplets. The KE_2EEA bipolymer could remove all emulsified water at 120 min of the assessment, whereas the KE_2EPA bipolymer reached at 92 vol % of efficiency at 180 min of the assessment. Regarding the B_37_2MEA bipolymer, it displays a null efficiency to remove the emulsified water, which could be due to, firstly, the low partition coefficient, and secondly, as it presents a high negative HE value, it acts more as a surfactant than a demulsifying agent, therefore, it forms another film around of the water droplet, stabilizing more the emulsion. Considering these results, changing the 2MEA for the 2EEA or 2EPA monomers, the bipolymer displays different chemical properties, and therefore, different behavior as demulsifying agent.
In response, the aforementioned difference of the biopolymers B_37_2MEA, KE_2EEA and KE_2EPA can not lead to the conclusion that changing the 2MEA for the 2EEA or 2EPA monomers will make the bipolymer displaying different chemical properties, because the biopolymers contain very different ratio of butyl acrylate:
Bipolymer_37_2MEA (Carbajal), with monomeric ratio of butyl acrylate/2- methoxyethyl acrylate of 30/70 w/w.
Bipolymer_KE_2EEA (present invention), with monomeric ratio of butyl acrylate/2- ethoxyethyl acrylate of 70/30 w/w.
Bipolymer_KE_2EPA (present invention), with monomeric ratio of butyl acrylate/2- ethoxypropyl acrylate of 70/30 w/w.
As the applicant pointed out, butyl acrylate is very different from 2EEA or 2EPA as it is hydrophobic and it confers to the bipolymer an excellent diffusion in crude oil. Bipolymer_37_2MEA contains only 30% butyl acrylate; whereas Bipolymer_KE_2EEA and Bipolymer_KE_2EPA each contains 70% butyl acrylate. Therefore, Bipolymer_37_2MEA is expected to display different property from Bipolymer_KE_2EEA and Bipolymer_KE_2EPA, due to the butyl acrylate content. Applicant did not prove that the property difference or performance difference is due to the difference among 2MEA, 2EEA, and 2EPA.
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.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 2 and 3 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Claim 2 recites the limitation “2-ethylhexyl acrylate”, "octyl acrylate" “2-ethylhexyl methacrylate”, and “octyl methacrylate”. There is insufficient antecedent basis for this limitation in the claim.
Claim 3 recites the limitation "2-methoxyethyl acrylate" and “2-methoxyethyl methacrylate”. There is insufficient antecedent basis for this limitation in the claim.
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 preferably from 7000 to 120 000 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 methoxymethyl (C2H5O), ethoxyethyl (C4H9O) , 3-methoxypropyl (C4H9O) or 3-ethoxypropyl (C5H11O). However, methoxymethyl, 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 methoxymethyl, 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 methoxymethyl, 2-ethoxyethyl, 3-methoxypropyl or 3-ethoxypropyl as a homolog of methoxyethyl, as methoxymethyl, 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 7000 to 120 000 Daltons falls within the recited range of 800-853,000 g/mol. 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
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any extension fee pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the date of this final action.
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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