Prosecution Insights
Last updated: July 17, 2026
Application No. 18/181,581

POLYIMIDE PRECURSOR, PREPARATION METHOD THEREOF, PHOTOSENSITIVE RESIN COMPOSITION AND CURED PRODUCT

Final Rejection §103
Filed
Mar 10, 2023
Priority
Mar 17, 2022 — TW 111109816
Examiner
FROST, ANTHONY J
Art Unit
1782
Tech Center
1700 — Chemical & Materials Engineering
Assignee
Echem Solutions Corp.
OA Round
2 (Final)
53%
Grant Probability
Moderate
3-4
OA Rounds
5m
Est. Remaining
73%
With Interview

Examiner Intelligence

Grants 53% of resolved cases
53%
Career Allowance Rate
342 granted / 650 resolved
-12.4% vs TC avg
Strong +20% interview lift
Without
With
+20.3%
Interview Lift
resolved cases with interview
Typical timeline
3y 9m
Avg Prosecution
39 currently pending
Career history
690
Total Applications
across all art units

Statute-Specific Performance

§101
0.1%
-39.9% vs TC avg
§103
97.0%
+57.0% vs TC avg
§102
1.1%
-38.9% vs TC avg
§112
0.9%
-39.1% vs TC avg
Black line = Tech Center average estimate • Based on career data from 650 resolved cases

Office Action

§103
DETAILED ACTION The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA . 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 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. Claim Rejections - 35 USC § 103 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 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) 1-10 and 16-20 is/are rejected under 35 U.S.C. 103 as being unpatentable over Ogawa et al. (WO 2020/189481, “Ogawa” a machine copy of which is provided and used as the citation copy unless otherwise noted) in view of Su et al. (US 2022/0306807, “Su”). Regarding claims 1, 16, 19, and 20, Ogawa teaches a photosensitive resin composition comprising a photoinitiator (in an amount of 0.1 to 30% by mass, pp. 27-28), a crosslinking monomer in an amount of from 1 to 15 parts by weight of a polyimide precursor (in an amount of from 0% to 60% by mass, and thus reading on from 1 to 15 parts by weight of the polyimide precursor, p. 33), a solvent (i.e., total solid content of from 5 to 80% reads on the claimed range of from 170 to 2000 parts by weight solvent content, pp. 33-34), and an additive (pp. 35-36), and the polyimide precursor obtained from a tetracarboxylic dianhydride (p. 4, 5), a diamine (p. 9, including diamine group), and a hydroxyl-containing alkyl (meth) acrylate (pp. 29-30, pp. 5-6, acrylate compound (III)). Further the composition need not include fluorine. Ogawa additionally teaches that the composition may be synthesized by reacting the dianhydride with a diamine and further with a carboxylic acid (pp. 14-18 and see synthesis examples pp. 44-48). The dianhydride and diamine form the mains chain of the polyimide precursor and the (meth)acylate forms a branch (see formula (1), pp. 10-11; and see original document, pp. 3-4). Ogawa additionally teaches that the precursor may be made into a resin and a cured product (pp. 3-4, 7, curable resin composition). Ogawa additionally teaches embodiments wherein the molar ratio of tetracarboxylic dianhydride to diamine may be on the range of around 1:1 (see, e.g., Synthesis example 1, p. 44, wherein 64.5 mmol dianhydride is reacted with 58.7 mmol diamine resulting in a ratio of dianhydride to diamine of 52%). A prima facie case of obviousness exists where the claimed ranges and prior art ranges do not overlap but are close enough that one skilled in the art would have expected them to have the same properties. Titanium Metals Corp. of America v. Banner, 778 F.2d 775, 227 USPQ 773 (Fed. Cir. 1985). See MPEP 2144.05. Furthermore, it should be noted that claim 1 includes product-by-process limitations. "[E]ven though product-by-process claims are limited by and defined by the process, determination of patentability is based on the product itself. The patentability of a product does not depend on its method of production. 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." In re Thorpe, 777 F.2d 695, 698, 227 USPQ 964, 966 (Fed. Cir. 1985). Please see MPEP 2113. In the present case, the method of making the polyimide precursor (i.e., by ring-opening substitution and polymerization), while expected to be the conventional manner of preparation, does not affect the structure of the claimed polyimide precursor, particularly in view of, for example, claim 6 wherein a conventional polyimide precursor is described. Therefore, Ogawa is considered to teach the presently claimed structure of a polyimide precursor. Ogawa fails to specifically teach that the tetracarboxylic dianhydride comprises p-phenylenebis(trimellitate anhydride) (hereafter referred to as “TAHQ”). In the same field of endeavor of polyimide films ([0009]), Su teaches that TAHQ may be beneficially used as a non-fluoro dianhydride in the creation of a polyimide useful for its low dielectric coefficient, low dielectric loss, low water absorption, and good frequency in addition to good chemical resistance (see [0012], [0014], describing a preference for TAHQ, and reading on the claimed dianhydride derivative Ar1 structure of claim 6). It therefore would have been obvious to have substituted the TAHQ of Su for the dianhydride of Ogawa for the benefit of its contribution to a polyimide film having good physical properties including low dielectric coefficient, low dielectric loss, low water absorption, and good frequency in addition to good chemical resistance (see [0012], [0014]). Regarding claim 2, Ogawa additionally teaches that the teatracarboxylic dianhydride may comprise, for example, 2,3,6,7-naphthalenetetracarboxyic dianhydride (e.g., p. 5). Regarding claim 3, Ogawa additionally teaches that the diamine may comprise, for example, 4,4’-diaminobiphenyl (e.g., p. 9). Regarding claim 4, Ogawa additionally teaches that the alkyl (meth)acrylate may comprise, for example, a hydroxyethyl (meth)acrylate (e.g., p. 31). Regarding claim 5, Ogawa additionally teaches embodiments wherein the total molar fraction of the alkyl (meth)acrylate may be on the range of from double the amount of the dianhydride used (Synthesis example 2 includes 129 mmol of 2-hydroxyethyl methacrylate to 64.5 mmol of dianhydride). A prima facie case of obviousness exists where the claimed ranges and prior art ranges do not overlap but are close enough that one skilled in the art would have expected them to have the same properties. Titanium Metals Corp. of America v. Banner, 778 F.2d 775, 227 USPQ 773 (Fed. Cir. 1985). See MPEP 2144.05. Regarding claim 6, Ogawa teaches a photosensitive resin composition comprising a photoinitiator (in an amount of 0.1 to 30% by mass, pp. 27-28), a crosslinking monomer in an amount of from 1 to 15 parts by weight of a polyimide precursor (in an amount of from 0% to 60% by mass, and thus reading on from 1 to 15 parts by weight of the polyimide precursor, p. 33), a solvent (i.e., total solid content of from 5 to 80% reads on the claimed range of from 170 to 2000 parts by weight solvent content, pp. 33-34), and an additive (pp. 35-36). Ogawa teaches the polyimide precursor may be obtained from a tetracarboxylic dianhydride (p. 4, 5), a diamine (p. 9, including diamine group), and a hydroxyl-containing alkyl (meth) acrylate (pp. 29-30, pp. 5-6, acrylate compound (III)). Further the composition need not include fluorine. Ogawa additionally teaches that the composition may be synthesized by reacting the dianhydride with a diamine and further with a carboxylic acid (pp. 14-18 and see synthesis examples pp. 44-48). The dianhydride and diamine form the mains chain of the polyimide precursor and the (meth)acylate forms a branch (see formula (1), pp. 10-11; and see original document, pp. 3-4). Ogawa additionally teaches that the precursor may be made into a resin and a cured product (pp. 3-4, 7, curable resin composition). Ogawa additionally teaches embodiments wherein the molar ratio of tetracarboxylic dianhydride to diamine may be on the range of around 1:1 (see, e.g., Synthesis example 1, p. 44, wherein 64.5 mmol dianhydride is reacted with 58.7 mmol diamine resulting in a ratio of dianhydride to diamine of 52%). Ogawa additionally teaches that the group corresponding to Ar1 may be a tetravalent organic group (e.g., pp. 15, 16; see original copy of Ogawa, p. 3). Ogawa additionally teaches that the units corresponding to those of the R1 and R2 groups may read on those claimed (e.g., may be a hydrogen, or ethylene carboxylic group, p. 13, 6, structure (III) wherein R201 may be an ethylene, p. 6; and see original copy of Ogawa, [0014], [0023] – [0026]). Further, the molar ratio of tetracarboxylic dianhydride to diamine may be on the range of around 1:1 (see, e.g., Synthesis example 1, p. 44, wherein 64.5 mmol dianhydride is reacted with 58.7 mmol diamine resulting in a ratio of dianhydride to diamine of 52%). A prima facie case of obviousness exists where the claimed ranges and prior art ranges do not overlap but are close enough that one skilled in the art would have expected them to have the same properties. Titanium Metals Corp. of America v. Banner, 778 F.2d 775, 227 USPQ 773 (Fed. Cir. 1985). See MPEP 2144.05. Ogawa fails to specifically teach that the tetracarboxylic dianhydride comprises p-phenylenebis(trimellitate anhydride) (hereafter referred to as “TAHQ”). In the same field of endeavor of polyimide films ([0009]), Su teaches that TAHQ may be beneficially used as a non-fluoro dianhydride in the creation of a polyimide useful for its low dielectric coefficient, low dielectric loss, low water absorption, and good frequency in addition to good chemical resistance (see [0012], [0014], describing a preference for TAHQ, and reading on the claimed dianhydride derivative Ar1 structure of claim 6). It therefore would have been obvious to have substituted the TAHQ of Su for the dianhydride of Ogawa for the benefit of its contribution to a polyimide film having good physical properties including low dielectric coefficient, low dielectric loss, low water absorption, and good frequency in addition to good chemical resistance (see [0012], [0014]). Regarding claim 8, Ogawa additionally teaches that the group corresponding to Ar2 may be among those claimed (e.g., pp. 13; and see original copy of Ogawa, pp. 3-4, structure corresponding to claimed first in series of structures of claim 8). Regarding claim 9, Ogawa additionally teaches that the units corresponding to those of the R1 and R2 groups may read on those claimed (e.g., may be a hydrogen, or ethylene carboxylic group, p. 13, 6, structure (III) wherein R201 may be an ethylene, p. 6; and see original copy of Ogawa, [0014], [0023] – [0026]). Regarding claim 10, Ogawa additionally teaches that the units corresponding to those of the R1 and R2 groups may read on those claimed (e.g., may be a hydrogen, or ethylene carboxylic group, p. 13, 6, structure (III) wherein R201 may be an ethylene, p. 6; and see original copy of Ogawa, [0014], [0023] – [0026]) and that the total molar fraction of each may be on the range of from 30% to 100% of the dianhydride used (Synthesis example 2 includes 129 mmol of 2-hydroxyethyl methacrylate to 64.5 mmol of dianhydride, being equivalent to R1+R2 and thus being roughly equivalent to a fraction of 100% by mol of the dianhydride). A prima facie case of obviousness exists where the claimed ranges and prior art ranges do not overlap but are close enough that one skilled in the art would have expected them to have the same properties. Titanium Metals Corp. of America v. Banner, 778 F.2d 775, 227 USPQ 773 (Fed. Cir. 1985). See MPEP 2144.05. Regarding claim 17, Ogawa additionally teaches that the resin composition may be included in an amount of up to 30% of the total composition (p. 15). The Examiner notes that in the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990). Please see MPEP 2144.05. Regarding claim 18, Ogawa additionally teaches the inclusion of a photoinitiator in an amount of 0.1 to 30% by mass (pp. 27-28), an additional crosslinking monomer in an amount of up to 60% by mass (p. 33), and a solvent in an amount reading on the claimed range (i.e., total solid content of from 5 to 80% reads on the claimed range of from 170 to 2000 parts by weight solvent content, pp. 33-34) and additionally teaches the inclusion of a component that may be a leveling agent (e.g., pp. 35-36, surfactants) and an adhesion promoter (e.g., metal adhesion promotors, p. 35). Response to Arguments Applicant’s arguments filed 4/24/26 are considered moot in light of the new grounds of rejection, which were necessitated by Applicant’s amendments. Arguments that are relevant to the current rejections are addressed below. Applicant argues that Ogawa fails to teach the inclusion of a crosslinking monomer in an amount of from 1 to 15 parts by weight based on 100 parts by weight of the polyimide precursor. However, Ogawa teaches the inclusion of benzoxazines as a crosslinking monomer in an amount of from 0% to 60% by mass (this amount would therefore read on from 1 to 15 parts by weight of the polyimide precursor, p. 33). Applicant cites to an example wherein the amount of crosslinking monomer exceeds from 1 to 15 parts by weight based on 100 parts polyimide precursor, but Ogawa also teaches the broader range of from 0 to 60% by weight, described above. “The use of patents as references is not limited to what the patentees describe as their own inventions or to the problems with which they are concerned. They are part of the literature of the art, relevant for all they contain.” In re Heck, 699 F.2d 1331, 1332-33, 216 USPQ 1038, 1039 (Fed. Cir. 1983) (quoting In re Lemelson, 397 F.2d 1006, 1009, 158 USPQ 275, 277 (CCPA 1968)). A reference may be relied upon for all that it would have reasonably suggested to one having ordinary skill the art, including nonpreferred embodiments. Merck & Co. v. Biocraft Laboratories, 874 F.2d 804, 10 USPQ2d 1843 (Fed. Cir.), cert. denied, 493 U.S. 975 (1989). Please see MPEP §2123. The applicant asserts that unexpected results overcome the obviousness rejection. The examiner respectfully disagrees. Although the applicant appears to have shown that the results are preferred, the applicant has failed to show that the results are necessarily unexpected and unexpected to a degree sufficient to overcome obviousness. Any differences between the claimed invention and the prior art may be expected to result in some differences in properties. The issue is whether the properties differ to such an extent that the difference is really unexpected. Please see MPEP §716.02. The burden is on the applicant to establish results are unexpected and significant. The evidence relied upon should establish that the differences in results are in fact unexpected, unobvious, commensurate in scope with the claims, and of both statistical and practical significance. See MPEP §716.02(b) and §716.02(d). The applicant is reminded that an affidavit or declaration must compare the claimed subject matter with the closest prior art to be effective to rebut a prima facie case of obviousness. See MPEP §716.02(e). Therefore, claims 1-6, 8-10, and 18-20 are rejected as described above. 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 nonprovisional extension fee (37 CFR 1.17(a)) 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 mailing date of this final action. Any inquiry concerning this communication or earlier communications from the examiner should be directed to ANTHONY J FROST whose telephone number is (571)270-5618. The examiner can normally be reached on Monday to Friday, 8:00am to 4:00pm. If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Aaron Austin, can be reached on 571-272-8935. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300. Information regarding the status of an application may be obtained from the Patent Application Information Retrieval (PAIR) system. Status information for published applications may be obtained from either Private PAIR or Public PAIR. Status information for unpublished applications is available through Private PAIR only. For more information about the PAIR system, see http://pair-direct.uspto.gov. Should you have questions on access to the Private PAIR system, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative or access to the automated information system, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000. /ANTHONY J FROST/Primary Examiner, Art Unit 1782
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Prosecution Timeline

Mar 10, 2023
Application Filed
Jan 26, 2026
Non-Final Rejection mailed — §103
Apr 24, 2026
Response Filed
Jun 23, 2026
Final Rejection mailed — §103 (current)

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Prosecution Projections

3-4
Expected OA Rounds
53%
Grant Probability
73%
With Interview (+20.3%)
3y 9m (~5m remaining)
Median Time to Grant
Moderate
PTA Risk
Based on 650 resolved cases by this examiner. Grant probability derived from career allowance rate.

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