Prosecution Insights
Last updated: April 19, 2026
Application No. 18/477,758

Novel diamine compound having low hygroscopicity and low dielectric constant, its polymer, and polyimide film using the polymer

Non-Final OA §102
Filed
Sep 29, 2023
Examiner
PAGANO, ALEXANDER R
Art Unit
1692
Tech Center
1600 — Biotechnology & Organic Chemistry
Assignee
Pusan National University Industry-University Cooperation Foundation
OA Round
1 (Non-Final)
79%
Grant Probability
Favorable
1-2
OA Rounds
2y 3m
To Grant
90%
With Interview

Examiner Intelligence

Grants 79% — above average
79%
Career Allow Rate
828 granted / 1049 resolved
+18.9% vs TC avg
Moderate +11% lift
Without
With
+11.3%
Interview Lift
resolved cases with interview
Typical timeline
2y 3m
Avg Prosecution
65 currently pending
Career history
1114
Total Applications
across all art units

Statute-Specific Performance

§101
2.4%
-37.6% vs TC avg
§103
27.3%
-12.7% vs TC avg
§102
32.6%
-7.4% vs TC avg
§112
19.6%
-20.4% vs TC avg
Black line = Tech Center average estimate • Based on career data from 1049 resolved cases

Office Action

§102
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 Claims 1-9 of C. Ha et al., US 18/477,758 (Sept. 29, 2023) are pending. Claims 1-9 are rejected. Objection to the Drawings The drawings are objected to under 37 CFR 1.83(b) because they are incomplete. The drawings are incomplete because in numerous instances, the text and chemical structures are too faint to be clearly discernable. For example, in Fig. 1, the chemical structure of the polyimide is indiscernible. In addition, the text under the arrows and chemical structures in Fig. 1 is too faint to be understood. In another example, in Fig. 2, the text above the 1H NMR spectra, as well as the numerical scaling of the axes is indiscernible. Numerous other occurrences of indiscernible, faint text appear in the drawings. Corrected drawing sheets in compliance with 37 CFR 1.121(d) are required in reply to the Office action to avoid abandonment of the application. Any amended replacement drawing sheet should include all of the figures appearing on the immediate prior version of the sheet, even if only one figure is being amended. The figure or figure number of an amended drawing should not be labeled as “amended.” If a drawing figure is to be canceled, the appropriate figure must be removed from the replacement sheet, and where necessary, the remaining figures must be renumbered and appropriate changes made to the brief description of the several views of the drawings for consistency. Additional replacement sheets may be necessary to show the renumbering of the remaining figures. Each drawing sheet submitted after the filing date of an application must be labeled in the top margin as either “Replacement Sheet” or “New Sheet” pursuant to 37 CFR 1.121(d). If the changes are not accepted by the examiner, the applicant will be notified and informed of any required corrective action in the next Office action. The objection to the drawings will not be held in abeyance. Objection to the Claims Claim 2 is objectionable because it is not punctuated with a period. Claim Rejections - 35 USC § 102 (AIA ) The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action: A person shall be entitled to a patent unless – (a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale or otherwise available to the public before the effective filing date of the claimed invention. (a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention. § 102(a)(1) Rejection over J. Lee et al., 14 Polymers, 1-17 (Oct. 25, 2022) (“Lee”) Prior Art Effect of Lee Lee is effective prior art under 35 USC § 102(a)(1) because it was published on October 25, 2022, less than one year before the instant presumed effective filing date of September 29, 2023.1 Lee names common and additional authors. In view of the common authors/inventors, Applicant may consider an exception under 35 U.S.C. 102(b)(1)(A) to overcome this rejection by a showing under 37 CFR 1.130(a) that the subject matter disclosed in the reference was obtained directly or indirectly from the inventor or a joint inventor of this application, and is therefore not prior art under 35 U.S.C. 102(a)(1). MPEP § 717(I)/(III). Alternatively, Applicant may consider (per footnote 1) filing a certified English-language translation of the certified copy of the foreign priority application KR 10-2022-0125434 (Sept. 30, 2022) for an effective filing date to obviate Lee as prior art, provided the priority application fully supports the claims pursuant to § 112(a). The § 102 Rejection Claims 1-9 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by J. Lee et al., 14 Polymers, 1-17 (published Oct. 25, 2022) (“Lee”). Lee discloses the following compound 1,2-DPEDBA: PNG media_image1.png 200 400 media_image1.png Greyscale which clearly anticipates claims 1 and 2. Respecting claims 3 and 4,2 Lee teaches that poly(amic acid) (PAA) was prepared by polycondensation polymerization between 2.0 mmol of the above 1,2-DPEDBA (933 mg) and 2.0 mmol of 4,4’-(hexafluoroisopropylidene)diphthalic anhydride (6-FDA) under a nitrogen atmosphere. Lee at page 4, “2.5. Preparation of 6FDA-DPEDBA PI and PMDA-ODA PI”. Lee depicts the polymerization reaction in Scheme 1. Lee at page 4, Scheme 1. Lee’s poly(amic acid) (PAA) (which is, per claims 3 and 4, a “polyimide precursor”)3 meets each and every limitation of claims 3 and 4. Claims 5-8 are also governed by product-by-process language. See footnote 2. Respecting claim 5, Lee teaches preparation of polyimide (PI) by adding 0.81 mL of pyridine and 1.89 mL of acetic anhydride to the above poly(amic acid) (PAA), under a nitrogen atmosphere, and stirring for 24 h, after which the solution was slowly poured into 200 mL of methanol and the precipitate was filtered and washed with deionized water and methanol and dried at 80 °C for 24 hours. Lee at page 4, “2.5. Preparation of 6FDA-DPEDBA PI and PMDA-ODA PI”. Each and every limitation of claim 5 is met by Lee. Respecting claim 6, Lee’s polyimide (PI) as depicted in Lee Scheme 1 is the same structure claimed. Lee at page 4, Scheme 1. The specification teaches preparation of the claimed polyimide using the same synthetic procedure as disclosed by Lee. See, specification at page 11, [0084]-[0085]. Lee variable “n” (per Lee Scheme 1) is asserted to have a value falling within the claim 6 range of 8 to 75. Once a reference teaching product appearing to be substantially identical is made the basis of a rejection, and the examiner presents evidence or reasoning to show inherency, the burden of production shifts to the applicant. MPEP § 2112(V) (citing In re Best, 562 F.2d 1252, 1255, 195 USPQ 430, 433-34 (CCPA 1977). Each and every limitation of claim 6 is met by Lee. Respecting claim 7, Lee teaches the solubility of the synthesized PI was tested by dissolving 10 mg of the PI powder into 1 mL of each organic solvent at room temperature in a test tube and as shown in Lee Table 1, the synthesized PI shows excellent solubility not only in common polar solvents with high boiling points, such as DMAc and DMF, but it is also soluble in common low-boiling point polar solvents, such as chloroform (CHCl3) and dichloromethane (CH2Cl2), at room temperature. Lee at page 10, 1st paragraph. Each and every limitation of claim 7 is met by Lee. Respecting claim 8, Lee teaches that the weight-average molecular weight of the PI was 2.37 [Symbol font/0xB4] 104 g mol-1, which falls within and anticipates the claim 8 range. Lee at page 8, last 4 lines. Each and every limitation of claim 8 is met by Lee. Respecting claim 9, Lee teaches preparation of a polyimide film (i.e., 6FDA-DPEDBA PI film) by dissolving the above formed poly(amic acid) (PAA) in [Symbol font/0x67]-butyrolactone at room temperature and casting on a glass substrate and drying at 80 °C for 24 hours. Lee at page 4, “2.5. Preparation of 6FDA-DPEDBA PI and PMDA-ODA PI”. Each and every limitation of claim 9 is met by Lee. No Additional Art Is Cited Against the Claims If Applicant overcomes the above rejection over J. Lee et al., 14 Polymers, 1-17 (Oct. 25, 2022) (“Lee”), claims 1-9 are otherwise free of the art of record. In that case, the closest art of record is L. Belin et al., US 2021/0179819 (2021). Belin discloses that aminobenzoate derivatives of formula (VI) are useful to prepare rubber compositions. PNG media_image2.png 200 400 media_image2.png Greyscale Belin at page 2, [0030]. In the above structure, n is 1 to 5, Ri may by hydrogen or alkyl and R1 and R2 are selected from the group consisting of a hydrogen atom and a methyl , ethyl , propyl , butyl , isopropyl , isobutyl, tert-butyl or benzyl group. Belin at page 2, [0026]-[0027]. The closest disclosed species is trimethylene bis(4-aminobenzoate). PNG media_image3.png 200 400 media_image3.png Greyscale (VII) Belin at page 5, [0090]. Compound (VII) differs from the claimed compound in propyl versus ethyl linkage and compound (VIII) lacks the claimed phenyl substituents. Neither Belin nor secondary art motivates one of ordinary skill to structurally modify Belin compound (VII) so as to arrive at compound falling within claim 1.4 Conclusion Any inquiry concerning this communication or earlier communications from the examiner should be directed to ALEXANDER R PAGANO whose telephone number is (571)270-3764. The examiner can normally be reached 8:00 AM through 5:00 PM. 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, Scarlett Goon can be reached at 571-270-5241. 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. ALEXANDER R. PAGANO Examiner Art Unit 1692 /ALEXANDER R PAGANO/Primary Examiner, Art Unit 1692 1 Applicant cannot rely upon the certified copies of the foreign priority applications KR 10-2022-0125434 (Sept. 30, 2022) or KR 10-2023-0001089 for an earlier effect filing date because translations of said applications have not been made of record in accordance with 37 CFR 1.55. When an English language translation of a non-English language foreign application is required, the translation must be that of the certified copy (of the foreign application as filed) submitted together with a statement that the translation of the certified copy is accurate. See MPEP §§ 215 and 216. 2 Claims 3 and 4 are claimed using product-by-process language. Even though product-by-process claims are limited by and defined by the process, determination of patentability is based on the product itself. MPEP § 2113(I). The patentability of a product does not depend on its method of production. MPEP § 2113(I). If the product in the product-by-process claim is the same as or obvious from a product of the prior art, the claim is unpatentable even though the prior product was made by a different process. MPEP § 2113(I) (citing In re Thorpe, 777 F.2d 695, 698, 227 USPQ 964, 966 (Fed. Cir. 1985)). 3 Note however that the claim 3 and 4 preamble term “polyimide precursor” is not a limitation because the body of a claim fully and intrinsically sets forth all of the limitations of the claimed invention, and the preamble merely states, for example, the purpose or intended use of the invention, rather than any distinct definition of any of the claimed invention’s limitations, then the preamble is not considered a limitation and is of no significance to claim construction. MPEP § 2112.02(II) (citing Rowe v. Dror, 112 F.3d 473, 478, 42 USPQ2d 1550, 1553 (Fed. Cir. 1997). 4 In the chemical arts, a "lead compound" obviousness analysis is often applied; the “lead compound” analysis requiring initial motivation to select a prior art compound and thereafter further motivation to make the specific structural modifications thereto so as to arrive at a claimed compound. See MPEP § 2143(B) (discussing “lead compound cases” in Examples 9-11 with respect to pharmaceutical applications).
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Prosecution Timeline

Sep 29, 2023
Application Filed
Feb 09, 2026
Non-Final Rejection — §102 (current)

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Study what changed to get past this examiner. Based on 5 most recent grants.

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Prosecution Projections

1-2
Expected OA Rounds
79%
Grant Probability
90%
With Interview (+11.3%)
2y 3m
Median Time to Grant
Low
PTA Risk
Based on 1049 resolved cases by this examiner. Grant probability derived from career allow rate.

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