Prosecution Insights
Last updated: August 06, 2026
Application No. 16/914,776

DEMULSIFYING AGENTS FOR CRUDE OIL BASED ON RANDOM ALKYLACRYLIC-AMINOALKYLACRYLIC-CARBOXYALKYLACRYLIC TERPOLYMERS OF CONTROLLED MOLECULAR MASS

Final Rejection §103
Filed
Jun 29, 2020
Priority
Feb 27, 2020 — MX MX/A/2020/002212
Examiner
XU, JIANGTIAN
Art Unit
1762
Tech Center
1700 — Chemical & Materials Engineering
Assignee
Instituto Mexicano del Petróleo
OA Round
6 (Final)
65%
Grant Probability
Favorable
7-8
OA Rounds
0m
Est. Remaining
99%
With Interview

Examiner Intelligence

Grants 65% — above average
65%
Career Allowance Rate
222 granted / 340 resolved
At TC average
Strong +34% interview lift
Without
With
+34.5%
Interview Lift
resolved cases with interview
Typical timeline
3y 3m
Avg Prosecution
68 currently pending
Career history
402
Total Applications
across all art units

Statute-Specific Performance

§101
1.0%
-39.0% vs TC avg
§103
56.4%
+16.4% vs TC avg
§102
14.3%
-25.7% vs TC avg
§112
24.2%
-15.8% vs TC avg
Black line = Tech Center average estimate • Based on career data from 340 resolved cases

Office Action

§103
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 . Claim Status The claims filed on 5/18/2026 have been entered. Claims 11 and 20 are amended. Claims 1-10 and 15 have been canceled. Claims 21-29 are new. Claim(s) 11-14 and 16-29 is/are pending and are under examination in this office action. Response to Arguments The Declaration under 37 CFR 1.132 filed 5/18/2026 is insufficient to overcome the rejection of claims 11-14 and 16-20 based upon 35 U.S.C. 103 as set forth in the last Office action because: Declarant argued that in the case of a bipolymer, only two reactivity parameters (r) and rz) are required to characterize the copolymerization behavior. However, terpolymerization involves eight distinct reactivity parameters (F121, [131, F123, 1212, [213] [231, [321, [323), reflecting the complex interactions between three different monomer types. For the specific case of carboxyacrylic and aminoacrylic monomers, there are no reported values of reactivity parameters for bipolymers, and even less for terpolymers, in the scientific literature. This absence of fundamental data makes it impossible to predict terpolymerization behavior from bipolymer data. Many combinations of monomers also suffer from anomalous effects, such as antepenultimate and penultimate effects, that affect the formation of the copolymer and the nature of monomer sequences in the copolymer chains. These effects are unpredictable and cannot be deduced from simpler systems. Based on the foregoing, it is not possible to predict the formation of a specific terpolymer with appropriate sequences and molecular weight from the synthesis parameters of two different bipolymers. The synthesis of KIC terpolymers had to be developed independently of the known physicochemical parameters used to prepare KI and KC bipolymers. In response, the examiner agrees with the Declarant in that terpolymerization is more complicated than bipolymerization. However, this does not prevent one of ordinary skill in the art at the time of filing to explore terpolymerization. For example, Behles (US 20070244248 A1, cited in the 103 rejection) teaches emulsion copolymerization of four monomers, useful as a demulsifier or water clarifier [abstract]. Declarant argued that as shown in Table 1, the terpolymer system is more reactive than the bipolymer systems (rKIC = 0.0022 g/mL-min versus rKC = 0.0011 g/mL. and rKl = 0.0016 g/mL/min). This increased reactivity was unexpected and could not have been predicted from the bipolymer data. A person of ordinary skill in the art could not have known that a semi- continuous reactor is required, operating under specific feeding conditions from a first tank containing the pre-emulsion and from a second tank containing the initiator solution. 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. Declarant 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, dehydrating activity is a property of the product and is expected to be present in the product. Applicants can rebut a prima facie case of obviousness by showing the criticality of the range, that the claimed range achieves unexpected results relative to the prior art range (MPEP2144.05.III). To establish unexpected results over a claimed range, applicants should compare a sufficient number of tests both inside and outside the claimed range to show the criticality of the claimed range. In re Hill, 284 F.2d 955, 128 USPQ 197 (CCPA 1960), MPEP 716.02(d). Whether unexpected results are the result of unexpectedly improved results or a property not taught by the prior art, the “objective evidence of nonobviousness must be commensurate in scope with the claims which the evidence is offered to support." In re Clemens, 622 F.2d 1029, 1036, 206 USPQ 289, 296 (CCPA 1980); MPEP 716.02(d). In the instant case, the examples are not commensurate in scope with the claims. For instance, claim 11 recites a random alkylacrylic-aminoacrylic-carboxyacrylic terpolymer comprising structural formula (1) which covers wide variety of terpolymers depending on the choice of R1, R2, R3, R4, R5, R6, x, y and z. However, the examples only employ one type of poly(alkyl-aminoalkyl-carboxyalkyl) with R1=n-butyl, R2=2-(dimethylamino)ethyl, R3=2-carboxyethyl, R4, R5, and R6=hydrogen, with seven combinations of x, y and z, corresponding to the AAmC-1 series and AAmC-2 series [0069 and 0070 PG PUB]. It is not known if poly(alkyl-aminoalkyl-carboxyalkyl) terpolymers with different R1, R2, R3, R4, R5 and R6 would give the same result. Claim 11 recites molar mass of the terpolymer to be 1,200-664,200. However, the terpolymers in the examples only range from 6,854-36,914 [Tables 1 and 2 PG PUB]. It is not known if terpolymers having molar mass of 1,200 and 664,200 would give the same result. Claim 11 recites alkylacrylic monomer at a concentration of between 50.0 and 60.0 wt%; aminoalkylacrylic monomer at a concentration of between 10 and 40 wt%; andcarboxyalkylacrylic monomer at a concentration of between 10 and 40 wt%. However, the examples only employ alkylacrylic monomer at a concentration of between 60.0 and 90.0 wt%; aminoalkylacrylic monomer at a concentration of between 5 and 30 wt%; andcarboxyalkylacrylic monomer at a concentration of between 5 and 30 wt% [Tables 1 and 2 PG PUB], which does not meet the claimed ranges. Since the examples are not reasonably commensurate with the full scope of claimed materials, and the Applicant has not provided any additional information that would allow one skilled in the art to extend the results associated with the data to the full scope of the claim, the examples cannot be relied upon to establish non-obviousness of the claimed invention. Declarant 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, applicant's argument in a brief cannot take the place of evidence. The Declarant provided no evidence to show that monomers of different partition coefficient and hydration energy cannot be copolymerized. Afterall, the prior art of Behles (US 20070244248 A1, cited in the 103 rejection) teaches emulsion copolymerization of 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). Declarant argued that Behles is different from the current invention in that it teaches a tetrapolymer (not a terpolymer) that is water-soluble, in a batch process. 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."). The 103 rejection is based on Carbajal et al (US 20180162975 A1) in view of Behles (US 20070244248 A1), and clearly stated why it is prima facie obvious to make a terpolymer based on the combination. Carbajal teaches emulsion copolymerization of aminoacrylics; and it is a semi-continuous process [abstract]. Declarant argued that as shown in Table 3, the terpolymer compositions exhibit distinctly different electrostatic potential values depending on whether the system is in a neutral state or an amphoteric (zwitterionic) state. The amphoteric state corresponds to the zwitterionic fragment discussed above, where the aminoalkyl acrylic monomer carries a positive charge and the carboxyalkyl acrylic monomer carries a negative charge. In response, Declarant did not provide evidence to show that difference in electrostatic potential values would prevent one of ordinary skill in the art at the time of filing from make a terpolymer. Applicant's arguments filed on 5/18/2026, with respect to 103 rejection have been fully considered but are not persuasive. Applicant’s arguments are based on the Declaration and are addressed above. 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 16-29 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 claims 11 and 21, 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 50-60 wt% of alkylacrylic monomer, 10-40 wt% of aminoalkylacrylic monomer, and 10-40 wt% of carboxyacrylic monomer in claim 11; and overlap the claimed ranges of 50-99 wt% of alkylacrylic monomer, 0.5-49.5 wt% of aminoalkylacrylic monomer, and 0.5-49.5 wt% of carboxyacrylic monomer in claim 21. Regarding claims 12 and 22, 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 claims 13 and 23, 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 claims 14 and 24, 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 and 25-27, 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 claims 19 and 28, Sandoval teaches that the copolymer concentration in the crude oil is between 10 and 2000 ppm [0073], meeting the claimed limitation. Regarding claims 20 and 29, 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 16-29 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 and 21, 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 50-60 wt% of alkylacrylic monomer, 10-40 wt% of aminoalkylacrylic monomer, and 10-40 wt% of carboxyacrylic monomer in claim 11; and overlap the claimed ranges of 50-99 wt% of alkylacrylic monomer, 0.5-49.5 wt% of aminoalkylacrylic monomer, and 0.5-49.5 wt% of carboxyacrylic monomer in claim 21. Regarding claims 12 and 22, 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 claims 13 and 23, 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 claims 14 and 24, Behles teaches 2-carboxyethyl (meth)acrylate [0016] as stated in claim 11 rejection above, meeting the clamed limitation. Regarding claims 16-18 and 25-27, 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 claims 19 and 28, Carbajal teaches that the copolymer concentration in the crude oil is between 10 and 2000 ppm [0082], meeting the claimed limitation. Regarding claims 20 and 29, 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 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. Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice. 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. Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000. /JIANGTIAN XU/Primary Examiner, Art Unit 1762
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Prosecution Timeline

Show 18 earlier events
Jan 30, 2025
Response after Non-Final Action
Oct 15, 2025
Response after Non-Final Action
Dec 16, 2025
Request for Continued Examination
Dec 18, 2025
Response after Non-Final Action
Mar 12, 2026
Non-Final Rejection mailed — §103
May 18, 2026
Response after Non-Final Action
May 18, 2026
Response Filed
Jun 05, 2026
Final Rejection mailed — §103 (current)

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2y 9m to grant Granted Jun 16, 2026
Patent 12649816
THERMOPLASTIC POLYURETHANES DERIVED FROM LIGNIN MONOMERS
3y 8m to grant Granted Jun 09, 2026
Study what changed to get past this examiner. Based on 5 most recent grants.

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Prosecution Projections

7-8
Expected OA Rounds
65%
Grant Probability
99%
With Interview (+34.5%)
3y 3m (~0m remaining)
Median Time to Grant
High
PTA Risk
Based on 340 resolved cases by this examiner. Grant probability derived from career allowance rate.

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