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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 12/16/2025 has been entered.
Claim Status
The claims filed on 12/16/2025 have been entered. No amendment is made. Claims 1-10 and 15 have been canceled. Claim(s) 11-14 and 16-20 is/are pending and are under examination in this office action.
Response to Arguments
Applicant's arguments filed on 12/16/2025, with respect to 103 rejection have been fully considered but are not persuasive.
Applicant argued that new evidence in Table 1 shows that it is impossible to know from bipolymerization parameters to deduce the formation of a terpolymer.
In response, the data in the attached Table 1 is parameters from each one of the references. There is no evidence to show that one of ordinary skill in the art at the time of filing would be prevented from making a terpolymer based on these parameters. Just because the parameters for making a bipolymer is different from making a terpolymer does not mean one of ordinary skill in the art could not develop new parameters in making a terpolymer. Afterall, even making different bipolymers may require different polymerization parameters. Therefore, these parameters cannot serve as evidence as to why a person of ordinary skill in the art capable of polymerizing alkylacrylic and carboxyacrylic monomers (Sandoval) and capable of polymerizing alkylacrylic and aminoacrylic monomer (Carbajal) also would not have been able to polymerize alkylacrylic, aminoacrylic, and carboxyacrylic monomers.
Applicant argued that the superior dehydrating activity of KIC random terpolymers compared to those of KC and KI bipolymers is reported in Figure 1.
In response, 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 evidence. Therefore, the recited new evidence cannot be relied upon to traverse the rejection. Nonetheless, dehydrating activity is a property of the product and is inherent to the product.
Applicant argued that aminoalkyl acrylic monomer and carboxyalkyl acrylic monomer present different partition coefficient and hydration energy. Thus, the presence of two hydrophilic centers induce a higher and differ with the polar centers of the asphaltene-resin agglomerates, promoting a mayor reduction of the superficial tension of the W/O interface in comparison with the bipolymers with only one hydrophilic center. Sandoval et al. and Carbajal et al. did not suggest that aminoacrylic monomers should not be used as comonomer, but they consider that the incorporation of aminoacrylic monomers is more difficult than the introduction of carboxyacrylic monomers in the bipolymer chains. This one is due to the high solubility of the aminoacrylic monomers in water and the risk of homopolymerization in the aqueous phase.
In response, attorney's argument in a brief cannot take the place of evidence. The applicant provides no evidence to show monomers of different partition coefficient and hydration energy cannot be copolymerized.
Applicant argued that aminoacrylics cannot polymerize by emulsion polymerization, because they homopolymerize in the aqueous phase, forming gels. It is not easy to incorporate the aminoacrylic monomers6 in a bipolymer or terpolymer chain. If an aminoacrylic, a carboxyacrylic and an alkylacrylic are just introduced in a batch reactor for emulsion polymerization, it is observed that only a small fraction of the carboxyacrylic and, especially, the aminoacrylic monomers will react with the emulsified alkylacrylic monomer. Most of the hydrophilic monomers will homopolymerize or bipolymerize in water7; a mixture of different polymers is obtained in this way. It is necessary to study experimentally the homopolymerization of individual monomers to design a homogeneous bipolymers. This difficulty increases in the case of a terpolymer9. Different terpolymerizations, at several addition feeding rates must be experimentally performed to synthesize a colloidally stable latex, made of homogeneous particles. More important, the obtained terpolymers should show an adequate composition, randomness and molecular weight to reach an improved dehydrating activity in crude oil. A person with ordinary skills could not know that a semi-continuous reactor is required, operating under specific feeding conditions from a first tank containing the pre-emulsion and from a second one containing the initiator solution.
In response, Carbajal teaches emulsion copolymerization of aminoacrylics; and it is a semi-continuous process [abstract].
Applicant argued that it is important to mention that two crude oils could have the same API gravity, and, however, their SARA compositions can be completely different, requiring different demulsification processes. The average molecular weight molecular of the polymers is an important aspect to consider in crude oil processing. Another point to be considered is the water droplet size, because it is not the same to treat an emulsion with a micrometric droplet size that to condition a crude oil emulsion with a nanometric size of the droplet. In both cases, the weight molecular of the terpolymer plays a key role in the dehydration process.
In response, again, Attorney's argument in a brief cannot take the place of evidence.
Applicant argued that the demulsifier reported by Behles et al. is utterly different from the acrylic random terpolymer of the presently claimed invention. This demulsifying agent consists of a terpolymer, made with some ionic monomers, which makes water soluble, hindering a fast diffusion through crude oil and decreasing its dehydrating activity. The tetrapolymer of Behles et al. was synthesized in a batch reactor, without control of its randomness and molecular weight. The teachings of this demulsifying technology could not be used to prepare the completely different random acrylic terpolymer of the presently claimed invention.
In response, the argument attacks Behles individually. See In re Keller, 642 F.2d 413, 426 (CCPA 1981) ("[O]ne cannot show non-obviousness by attacking references individually where, as here, the rejections are based on combinations of references."). Attorney's argument in a brief cannot take the place of evidence. The applicant provides no evidence or technical reasoning as to why a person of ordinary skill in the art capable of polymerizing alkylacrylic and carboxyacrylic monomers (Sandoval) and capable of polymerizing alkylacrylic and aminoacrylic monomers (Carbajal) also would not have been able to polymerize alkylacrylic,aminoacrylic, and carboxyacrylic monomers.
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) 11-14 and 16-20 is/are rejected under 35 U.S.C. 103 as being unpatentable over Sandoval et al (US 20190276750 A1) in view of Carbajal et al (US 20180162975 A1).
Regarding claim 11, Sandoval teaches alkylacrylic-carboxyalkylacrylic random copolymers as demulsifier for crude oils with densities between 5 and 40° API [abstract, 0002]. The copolymer structure is represented by formula (2) [0061], where R1 and R3 ═H (hydrogen), CH3 (methyl); R2 =(methyl), C2H5 (ethyl), C4H9 (n-butyl, isobutyl), C6H13 (n-hexyl, iso-hexyl), C8H17 (2 ethyl-hexyl), C8H17 (n-octyl), C10H21 (n-decyl, iso-decyl), C12H25 (n-dodecyl), C18H37 (n-octadecyl), C8H9O (2-phenoxyethyl), C3H7O (2-methoxyethyl), C5H11O2 (2-(2-methoxyethoxy)ethyl). This aliphatic chain may contain heteroatoms of the ether group, as well as aromatic rings or rings with heteroatoms of the ether type; R4 ═C3H5O2 (carboxyethyl), C4H7O2 (carboxypropyl), C5H9O2 (carboxybutyl); x=is a number comprised in the range from 4 to 900; y=is a number comprised in the range from 4 to 900; “x” and “y” can be random sequences; and average number molecular masses are comprised in the ranges from 900 to 472,500 g/mol [0062-0071].
The examiner submits that the repeating unit of x and y in Sandoval’s structure reads on the repeating unit of x and z in the claimed formula (1). Sandoval’s densities between 5 and 40° API overlaps the claimed densities from 3 and 40° API. Sandoval’s molecular masses from 900 to 472,500 g/mol overlaps the claimed molecular masses within 1,200 and 664,200 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).
Sandoval does not teach the repeating unit y in the claimed formula (1).
In the same field of endeavor, Carbajal teaches alkyacrylic-aminoacrylic random copolymers as demulsifier for crude oils with densities between 10 and 40° API [abstract, 0002]. The copolymer structure is represented by formula (2) [0070], where R1 and R3 ═H (hydrogen), CH3 (methyl); R2 =(methyl), C2H5 (ethyl), C4H9 (n-butyl, isobutyl), C6H13 (n-hexyl, iso-hexyl), C8H17 (2 ethyl-hexyl), C8H17 (n-octyl), C10H21 (n-decyl, iso-decyl), C12H25 (n-dodecyl), C18H37 (n-octadecyl), C8H9O (2-phenoxyethyl), C3H7O (2-methoxyethyl), C5H11O2 (2-(2-methoxyethoxy)ethyl). This aliphatic chain may contain heteroatoms of the ether group, as well as aromatic rings or rings with heteroatoms of the ether type; R4 ═ CH2NH2 (methylamine), CH2CH2NH2 (2-ethylamine), CH2CH2CH2NH2 (3-propylamine), CH2CH(NH2)2 (2-dimethylamino), (CH2CH2N(CH3)2) 2-(dimethylamino)ethyl, (CH2CH2N(CH2CH3)2) 2-(dimethylamino)ethyl, (CH2CH2CH2N(CH3)2) 3-(dimethylamino)propyl, (C6H12NO) N-ethylmorpholine.; x=is a number comprised in the range from 2 to 900; y=is a number comprised in the range from 2 to 900; “x” and “y” can be random sequences; and average number molecular masses are comprised in the ranges from 1000 to 180,000 g/mol [0071-0079].
The examiner submits that the repeating unit of x and y in Carbajal’s structure reads on the repeating unit of x and y in the claimed formula (1). Carbajal’s densities between 5 and 40° API overlaps the claimed densities from 10 and 40° API. Carbajal’s molecular masses from 1000 to 180,000 g/mol overlaps the claimed molecular masses within 1,200 and 664,200 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).
Carbajal teaches that random copolymers of acrylic and aminoacrylic monomers have properties as breakers of water/crude oil emulsions and the proportions of the acrylic and aminoacrylic monomers can be adjusted [0028]. Sandoval teaches that with the combination of a carboxyacrylic monomer and another amino acrylic, high demulsifying rates were achieved [0016]. Therefore, it would be obvious for one of ordinary skill in the art at the time of filing to combine amino acrylic unit into Sandoval’s copolymer in order to achieve high demulsifying rates, therefore, forming a random alkylacrylic-aminoacrylic-carboxyacrylic terpolymer. It would also be obvious to one of ordinary skill in the art at the time of filing to select Carbajal’s repeating unit y as the amino acrylic unit in the modified Sandoval’s terpolymer, as it is expressly disclosed as being suitable for use in (meth)acrylate-based demulsifying random copolymers. 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.
Sandoval’s Tables 1 and 2 show that an alkylacrylic monomer may be included in amounts of 60-80 wt%, and a carboxyacrylic monomer may be included in amounts of 20-40 wt%. Carbajal’s Tables 2-4 show that an alkylacrylic monomer may be included in amounts of 60-90 wt%, and an aminoalkylacrylic monomer may be included in amounts of 10-40 wt%. These ranges overlap the claimed ranges of 50-90 wt% of alkylacrylic monomer and 0.5-49.5 wt% of aminoalkylacrylic monomer and carboxyacrylic monomer.
Regarding claim 12, Sandoval teaches that the alkylacrylic monomer is selected from methyl acrylate, ethyl acrylate, butyl acrylate, n-amyl acrylate, isobornyl acrylate isobutyl acrylate, tert-butyl acrylate, hexyl acrylate, 2-ethylhexyl acrylate, 3,5,5-trimethylhexyl acrylate, 2-methoxiethyl acrylate, 2-phenoxiethyl acrylate, 4-tert-butylcyclohexyl acrylate, octyl acrylate, isodecyl acrylate, decyl acrylate, lauryl acrylate, tridecyl acrylate, octadecyl acrylate or behenyl acrylate [0072], meeting the claimed limitation.
Regarding claim 13, Carbajal teaches that the alkylamino acrylate is selected from 2-ethylamino acrylate, 2-ethylamino methacrylate, 2-(dimethylamino)ethyl acrylate, 2-(dimethylamino)ethyl methacrylate, 3-propylamino acrylate, 3-(dimethylamino)propyl acrylate, 2-(diethylamino)ethyl acrylate, 2-(diethylamino)ethyl methacrylate, 2-N-ethylmopholine methacrylate [0081], meeting the claimed limitation.
Regarding claim 14, Sandoval teaches that the carboxyalkyl acrylate is selected from 2-carboxyethyl acrylate, 3-carboxypropyl acrylate, 4-carboxybutyl acrylate, 2-carboxyethyl methacrylate, 3 -carboxypropyl methacrylate and 4-carboxybutyl methacrylate [0072], meeting the clamed limitation.
Regarding claims 16-18, Sandoval teaches that the composition comprises solvent such as dichloromethane, methanol, ethanol, isopropanol, chloroform, benzene and its derivatives, toluene, xylene, naphtha; and the amount of copolymer in the solution is between 10 to 50 wt % [0060].
Regarding claim 19, Sandoval teaches that the copolymer concentration in the crude oil is between 10 and 2000 ppm [0073], meeting the claimed limitation.
Regarding claim 20, Sandoval’s Tables 1 and 2 show that an alkylacrylic monomer may be included in amounts of 60-80 wt%, and a carboxyacrylic monomer may be included in amounts of 20-40 wt%. Carbajal’s Tables 2-4 show that an alkylacrylic monomer may be included in amounts of 60-90 wt%, and an aminoalkylacrylic monomer may be included in amounts of 10-40 wt%.
These ranges suggest the terpolymer composition of A at 60-90 wt%, Am at 10-40 wt%, and C at 20-40 wt%, overlapping the claimed A-Am-C at 60-10-30 wt%, A-Am-C at 60-20-20 wt%; A- Am-C at 70-10-20 wt%.
Claim(s) 11-14 and 16-20 is/are rejected under 35 U.S.C. 103 as being unpatentable over Carbajal et al (US 20180162975 A1) in view of Behles (US 20070244248 A1).
Regarding claim 11, Carbajal teaches alkyacrylic-aminoacrylic random copolymers as demulsifier for crude oils with densities between 10 and 40° API [abstract, 0002]. The copolymer structure is represented by formula (2) [0070], where R1 and R3 ═H (hydrogen), CH3 (methyl); R2 =(methyl), C2H5 (ethyl), C4H9 (n-butyl, isobutyl), C6H13 (n-hexyl, iso-hexyl), C8H17 (2 ethyl-hexyl), C8H17 (n-octyl), C10H21 (n-decyl, iso-decyl), C12H25 (n-dodecyl), C18H37 (n-octadecyl), C8H9O (2-phenoxyethyl), C3H7O (2-methoxyethyl), C5H11O2 (2-(2-methoxyethoxy)ethyl). This aliphatic chain may contain heteroatoms of the ether group, as well as aromatic rings or rings with heteroatoms of the ether type; R4 ═ CH2NH2 (methylamine), CH2CH2NH2 (2-ethylamine), CH2CH2CH2NH2 (3-propylamine), CH2CH(NH2)2 (2-dimethylamino), (CH2CH2N(CH3)2) 2-(dimethylamino)ethyl, (CH2CH2N(CH2CH3)2) 2-(dimethylamino)ethyl, (CH2CH2CH2N(CH3)2) 3-(dimethylamino)propyl, (C6H12NO) N-ethylmorpholine.; x=is a number comprised in the range from 2 to 900; y=is a number comprised in the range from 2 to 900; “x” and “y” can be random sequences; and average number molecular masses are comprised in the ranges from 1000 to 180,000 g/mol [0071-0079].
The examiner submits that the repeating unit of x and y in Carbajal’s structure reads on the repeating unit of x and y in the claimed formula (1). Carbajal’s densities between 5 and 40° API overlaps the claimed densities from 10 and 40° API. Carbajal’s molecular masses from 1000 to 180,000 g/mol overlaps the claimed molecular masses within 1,200 and 664,200 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).
Carbajal does not teach the repeating unit of z in the claimed formula (1) comprising a carboxyacrylic monomer. However, Carbajal does teach demulsifiers based on alkyl (meth)acrylates [0081] and amino-functional (meth)acrylates like N-2-morpholinoethyl acrylate [0081].
In the same field of endeavor, Behles teaches that ionizable monomers like 2-carboxyethyl (meth)acrylate [0016] (equivalent to the claimed z monomer) are suitable for use in combination with alkyl (meth)acrylates [0015] (equivalent to the claimed x monomer) and amino-functional (meth)acrylates like N-2-morpholinoethyl (meth)acrylate [0017] (equivalent to the claimed y monomer). Behles also recognizes that 2-carboxyethyl (meth)acrylate and N-2-morpholinoethyl (meth)acrylate are equivalents in that both are hydrophilic monomers with polymerizable double bonds suitable for inclusion in demulsifying copolymers [0017].
Therefore, it would be obvious for one of ordinary skill in the art at the time of filing to combine monomers like 2-carboxyethyl (meth)acrylate into Carbajal’s copolymer, as it is expressly disclosed as being suitable for use as a hydrophilic monomer in (meth)acrylate-based demulsifying random copolymers. 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.
Alternatively, it would have been obvious to combine Carbajal’s amino-functional (meth)acrylate with 2-carboxyethyl (meth)acrylate because Behles recognizes these as equivalents suitable for the same purpose. It is prima facie obvious to combine equivalent materials when the equivalence is recognized by the prior art. See MPEP 2144.06.
Carbajal’s Tables 2-4 show that an alkylacrylic monomer may be included in amounts of 60-90 wt%, and an aminoalkylacrylic monomer may be included in amounts of 10-40 wt%. Since 2-carboxyethyl (meth)acrylate is recognized as equivalent to aminoalkylacrylic monomer as stated in claim 11 rejection, it would be obvious for one of ordinary skill in the art at the time of filing to use the same amount of 2-carboxyethyl (meth)acrylate as aminoalkylacrylic monomer in the composition.
These ranges overlap the claimed ranges of 50-90 wt% of alkylacrylic monomer and 0.5-49.5 wt% of aminoalkylacrylic monomer and carboxyacrylic monomer.
Regarding claim 12, Carbajal teaches that the alkylacrylic monomer is selected from methyl acrylate, ethyl acrylate, butyl acrylate, n-amyl acrylate, isobornyl acrylate isobutyl acrylate, tert-butyl acrylate, hexyl acrylate, 2-ethylhexyl acrylate, 3,5,5-trimethylhexyl acrylate, 2-methoxiethyl acrylate, 2-phenoxiethyl acrylate, 4-tert-butylcyclohexyl acrylate, octyl acrylate, isodecyl acrylate, decyl acrylate, lauryl acrylate, tridecyl acrylate, octadecyl acrylate or behenyl acrylate [0081], meeting the claimed limitation.
Regarding claim 13, Carbajal teaches that the alkylamino acrylate is selected from 2-ethylamino acrylate, 2-ethylamino methacrylate, 2-(dimethylamino)ethyl acrylate, 2-(dimethylamino)ethyl methacrylate, 3-propylamino acrylate, 3-(dimethylamino)propyl acrylate, 2-(diethylamino)ethyl acrylate, 2-(diethylamino)ethyl methacrylate, 2-N-ethylmopholine methacrylate [0081], meeting the claimed limitation.
Regarding claim 14, Behles teaches 2-carboxyethyl (meth)acrylate [0016] as stated in claim 11 rejection above, meeting the clamed limitation.
Regarding claims 16-18, Carbajal teaches that the composition comprises solvent such as dichloromethane, methanol, ethanol, isopropanol, chloroform, benzene and its derivatives, toluene, xylene, naphtha; and the amount of copolymer in the solution is between 10 to 50 wt % [0069].
Regarding claim 19, Carbajal teaches that the copolymer concentration in the crude oil is between 10 and 2000 ppm [0082], meeting the claimed limitation.
Regarding claim 20, Carbajal’s Tables 2-4 show that an alkylacrylic monomer may be included in amounts of 60-90 wt%, and an aminoalkylacrylic monomer may be included in amounts of 10-40 wt%. Since 2-carboxyethyl (meth)acrylate is recognized as equivalent to aminoalkylacrylic monomer as stated in claim 11 rejection, it would be obvious for one of ordinary skill in the art at the time of filing to use the same amount of 2-carboxyethyl (meth)acrylate as aminoalkylacrylic monomer in the composition.
These ranges suggest the terpolymer composition of A at 60-90 wt%, Am at 10-40 wt%, and C at 10-40 wt%, overlapping the claimed A-Am-C at 60-10-30 wt%; A-Am-C at 60-20-20 wt%; A-Am-C at 60-30-10 wt%; A- Am-C at 70-10-20 wt%; A-Am-C at 70-20-10 wt%; A-Am-C at 80-10-10 wt%.
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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/JIANGTIAN XU/Primary Examiner, Art Unit 1762