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 .
Claims 1, 3, 4, 8 and 10-12 are pending as amended on 5/27/2026.
This action is properly made final, because the modified grounds of rejection set forth below were necessitated by Applicant’s amendment changing the scope of the claims. Claim 1 has been amended to require a specific combination of structural units (i.e., to require units according to each of formulas 5, 6, 7 and 8). The amendment to claim 1 excludes the species of polyimide exemplified in instant examples 19-20, which was elected for examination in the response filed on 5/1/2025, and which was previously encompassed by claim 1. The species of instant examples 19-20 has units derived from diamine monomers B-2, B-3, B-4 and B-5 (see Table 1 on p 210). The instant exemplified monomers B-2, B-4 and B-5 contain units according to presently recited formulas 5, 8 and 9, respectively. However, instant diamine monomer B-3 used to form instant examples 19-20 does not contain a unit corresponding to instant formula 6. Diamine monomer B-3 in the instant examples is 1,4-bis(4-aminophenoxy)benzene, while instant formula 6 in claim 1 is a unit derived from 1,3-bis(4-aminophenoxy)benzene. Because instant claim 1 no longer encompasses the elected species, examination has been continued for the species to which claim 1 is now limited. Claims 3 and 4 are no longer withdrawn from consideration because they are drawn to the species recited in amended claim 1.
Any rejections and/or objections made in the previous Office action and not repeated below are hereby withdrawn. The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office Action.
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 1, 4, 8 and 10-12 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 1 recites a first structural unit represented by formula 5 and a structural unit represented by formula 6, and a second structural unit comprising a structural unit represented by formula 8 and a structural unit represented by formula 9. Because the word “comprising” follows “second structural unit,” it is clear that the both the units of formula 8 and formula 9 are considered part of the “second structural unit.” However, it is unclear whether the “first structural unit” recited in claim 1 is only the structural unit of formula 5, or, whether the “first structural unit” includes both the formula 5 and the formula 6. Additionally, while the term “comprising” indicates that unrecited units other than formula 8 and formula 9 could form a part of the recited “second structural unit,” it is unclear whether the recited “first structural unit” is similarly open-ended, or, whether the first structural unit consists of a unit of formula 5 (or, consists of units of formula 5 and formula 6). Because it is not clear what units should be considered part of the “first structural unit,” one would not know how to determine a molar ratio of first structural unit to second structural unit, as recited in claim 1, rendering the scope of claim 1 (and dependent claims) unclear.
For examination purposes, claim 1 has been interpreted according to the language set forth in dependent claim 3, which makes clear that both formulas 5 and 6 are meant to be included within the “first structural unit,” and, clarifies that the first structural unit is open-ended (“comprises”), and could therefore include unrecited units in addition to the units of formulas 5 and 6.
Claim Rejections - 35 USC § 103
Claim(s) 1, 3, 4, 8, 10 and 11 are rejected under 35 U.S.C. 103 as being unpatentable over Hasegawa et al (JP 2009286706 A; machine translation cited herein) in view of Poe et al (US 2012/0190802) and Schork (Control of Polymerization Reactors, 1993, Marcel Dekker, p 52).
As to claims 1, 3, 4 and 11, Hasegawa discloses a polyimide film [0141] comprising a polyimide:
PNG
media_image1.png
85
222
media_image1.png
Greyscale
Wherein X is a tetravalent cyclohexane group and A is a divalent group [0026-28], formed by reaction of 1,2,4,5-cyclohexanetetracarboxylic dianhydride (CHTCA) [0033] with diamine [0066]. Hasegawa names several examples of diamine monomers in [0069].
The diamines named in [0069] include ether-containing diamines which have structures according to the presently recited “first” structural unit comprising a unit according to formula 5 and a unit according to formula 6 (i.e., named diamines include 1,3-bis(3-aminophenoxy)benzene [corresponding to instant exemplified diamine B-2, and to instant formula 5] and 1,3-bis(4-aminophenoxy)benzene [corresponding to instant formula 6]). The diamines named in [0069] also include ether-containing diamines which have structures according to the presently recited “second” structural unit formulas 8 and 9 (i.e., named diamines include bis(4-(3-aminophenoxy)phenyl)sulfone [corresponding to instant diamine B-4 and formula 8] and bis(4-(4-aminophenoxy)phenyl)sulfone) [corresponding to instant diamine B-5 and formula 9]). Hasegawa also exemplifies polyimides formed from reacting:
CHTCA with 1,4-bis(4-aminophenoxy)benzene (“TPE-Q”), Example 4, [0144];
CHTCA with 1,3-bis(4-aminophenoxy)benzene (“TPE-R”), Example 5 [0145] (TPE-R has a structure according to instant formula 6);
CHTCA with bis(4-(4-aminophenoxy)phenyl)sulfone (“BAPS”) Example 8, [0148] (BAPS has a structure according to instant formula 9 and is the same as instant diamine B-5).
Hasegawa teaches that the diamines may be used alone or in combination of two or more thereof [0069] (emphasis added). In Table 1 [0142], Hasegawa compares the properties of various polyimides which have the same dianhydride structure (CHTCA) and different diamine unit structures. Hasegawa’s examples show that for a polyimide wherein the dianhydride component is CHTCA, changing the diamine monomer constituent of the polyimide results in changes in various thermal, optical and mechanical properties of the polyimide. However, Hasegawa does not exemplify a CHTCA-derived polyimide wherein the diamine component provides a combination of units according to instant formulas 5, 6, 8 and 9.
Poe provides a discussion which shows the general level of knowledge in the art regarding structure/property relationships in polyimides. Poe teaches that polyimides are a type of polymer with many desirable properties [0017], usually formed from a diamine monomer and a “diacid monomer” (which is defined to include a dianhydride) [0018]. Poe teaches that it is possible to mix different varieties of each type of monomer, such that two or more dianhydride monomers and two or more diamine monomers can be included in the reaction vessel. The monomer constituents of each polymer chain can be varied to produce polyimides with different properties [0020-21]; the characteristics or properties of the final polymer are significantly impacted by the choice of monomers which are used to produce the polymer [0026].
Schork teaches that the ability to create a macromolecule containing two or more types of monomer units gives the polymer chemist a greatly increased ability to custom design a polymer to yield specific end-use properties (p 52, first paragraph). Schork teaches that as a general rule, a copolymer from monomers A and B will have properties intermediate between those of the two homopolymers of A and B, with the percent of A units in the polymer determining whether the copolymer more nearly resembles homopolymer A or B. See 2.3.1 on p 52.
Considering the disclosures of Poe and Schork, the person having ordinary skill in the art would have been motivated to form a polyimide from two or more types of a dianhydride and/or diamine monomer in order to vary the properties of the resulting polyimide. The person having ordinary skill in the art would have been motivated to select appropriate comonomer structures, and appropriate amounts of each comonomer, depending on the desired balance of final characteristics or properties (including thermal, mechanical and optical properties) in the final polymer. It would have been obvious to the person having ordinary skill in the art, therefore, to have prepared a polyimide by reaction of CHTCA dianhydride with two or more diamines, as disclosed by Hasegawa, by selecting any appropriate combination of two or more diamines named by Hasegawa in [0069], including, e.g., a combination of 1,3-bis(3-aminophenoxy)benzene (providing units according to instant formula 5), 1,3-bis(4-aminophenoxy)benzene (providing units according to instant formula 6), bis(4-(3-aminophenoxy)phenyl)sulfone (providing units according to instant formula 8), and bis(4-(4-aminophenoxy)phenyl)sulfone (providing units according to instant formula 9), in order to produce a polyimide and polyimide film having a balance of the properties associated with each of the diamines within the combination, and suitable for the various types of applications taught by Hasegawa [0001].
Considering Schork, it would have been further obvious to the person having ordinary skill in the art to have selected any appropriate amount of each diamine comonomer in order to achieve the desired resemblance of the overall copolymer to any one homopolymer formed from each of the respective diamine comonomers, including diamine comonomer amounts such that the bis(aminophenoxy)benzene monomers (according to instant formulas 5 and 6) and BAPS monomers (according to instant formulas 8 and 9) are in a 1:1 ratio, and further including amounts such that the meta-linked BAPS (according to instant formula 8) and para-linked BAPS (according to instant formula 9) are in a ratio within the instant range of 8:2 and 6:4, and such that the all-meta linked bis(aminophenoxy)benzene (formula 5) and the para-meta-para linked bis(aminophenoxy)benzene (formula 6) are in a ratio within the instant range of 6:4 to 2:8 (as recited in claim 4).
As to the presently recited weight average molecular weight recited in claim 1 and the intrinsic viscosity recited in claim 8: Hasegawa discloses that the CHTCA monomer has extremely high polymerizability, and that the intrinsic viscosity of the polyamic acid precursor is 0.5-3.8 dL/g [0036]. Hasegawa teaches that the higher the intrinsic viscosity the better, preferably 1.0 dL/g or more, otherwise the film forming property is deteriorated and cracking of the cast film may occur [0078]. A sufficient degree of polymerization is also taught to be associated with a high enough molecular weight to achieve sufficient film toughness [0004, 0031]. Considering Hasegawa’s disclosure, the person having ordinary skill in the art would have been motivated to select an appropriately high intrinsic viscosity in order to ensure high molecular weight, and desired film forming property and toughness. It would have been obvious to the person having ordinary skill in the art, therefore, to have formed a polyamic acid precursor having any intrinsic viscosity within Hasegawa’s disclosed range of 0.5-3.8 dL/g, including an intrinsic viscosity which corresponds to a polyimide intrinsic viscosity and polyimide molecular weight within the presently claimed ranges.
As to claim 10, modified Hasegawa suggests a polyimide according to claim 1, as set forth above. Hasegawa teaches that the glass transition temperature of the polyimide is preferably 230 C or higher when used as a display substrate [0110], which overlaps the presently claimed range of 200 to 400 C. It would have been obvious to the person having ordinary skill in the art to have formed a polyimide, as suggested by modified Hasegawa, having any Tg within Hasegawa’s disclosed range in order to ensure suitability as a display substrate, including a Tg within the presently claimed range. Case law has established that a prima facie case of obviousness is established where the claimed ranges overlap the ranges disclosed by the prior art. See MPEP 2144.05.
Claim(s) 12 is rejected under 35 U.S.C. 103 as being unpatentable over Hasegawa et al (JP 2009286706 A; machine translation cited herein) in view of Poe et al (US 20120190802) and Schork (Control of Polymerization Reactors, 1993, Marcel Dekker, p 52), and further in view of Hong et al (US 2020/0353668).
The rejection of claims 1 and 11 over Hasegawa in view of Poe and Schork is incorporated here by reference.
Hasegawa teaches a substrate for a display which may contain the polyimide, and which is excellent in transparency and flexibility [0109]. Hasegawa teaches that the light transmission in the 400 nm region, which is an indicator of clarity, is preferably at least 70%, and even more preferably 80% [0110]. However, Hasegawa fails to teach the yellow index at 70 micron or the light transmittance at 550 nm.
Like Hasegawa, Hong teaches a polyimide film which is advantageous for use as a substrate for various applications of flexible display devices [0015-16, 0099]. Hong discloses that if the yellowness (YI) is excessively high, the polyimide is limited in use as a display material [0032]. Hong teaches a film thickness of 25-150 microns [0056], a yellowness which is preferably 4.0 or less, and a light transmittance which is preferably 88% or more at 550 nm [0058]. Considering Hong’s disclosure, when forming a polyimide film intended for use as a display substrate material, one having ordinary skill in the art would have been motivated to form a film having any desired thickness within Hong’s disclosed range of 25-150 microns, and to target a yellowness index of 4.0 or less and a 550 nm light transmittance of 88% or more, in order to provide the properties (thickness, transparency and colorlessness) required for use as a display substrate. It would have been obvious to the person having ordinary skill in the art, therefore, to have formed a polyimide film, as suggested by modified Hasegawa, having any appropriate thickness within Hong’s range of 25-150 microns (including 70 microns), and having a yellow index and 550 nm transmittance within Hong’s disclosed ranges, thereby arriving at the presently claimed subject matter.
Response to Arguments
Applicant's arguments filed 5/27/26 have been fully considered.
On pages 6-7, Applicant argues that in examples 19 and 20, both heat resistance and mechanical strength are improved. The examiner notes that there are no examples in the instant specification nor in the Declaration filed on 12/18/2025 which are representative of polyimides according to the claims as presently amended. As discussed above, instant claim 1 requires units according to instant formula 6. None of the polyimides of Applicant’s examples have units according to instant formula 6 (i.e., units derived from 1,3-bis(4-aminophenoxy)benzene). Therefore, any improvements or unexpected results demonstrated in the instant examples do not necessarily establish that such improvements or unexpected results would be exhibited by a polyimide according to the instant claims.
Applicant argues (p 7) that Schork’s disclosure pertains to a single property being an intermediate value in a copolymer, and optimizing multiple properties is outside the scope of Schork’s teaching. Applicant has not provided explanation or evidence as to why one would infer from Schork’s disclosure that a copolymer would have only a single property which is intermediate between respective homopolymers. Note also that Schork discloses intermediate “properties” (plural) in line 5 of section 2.3.1. Therefore, Applicant has not established that optimizing multiple properties via copolymerization would be outside the scope of Schork’s teaching.
Applicant argues (p 8) that Additional examples 1 to 4 (see 12/18/25 Dec) establish that effects relating to thermal stability are superior compared to examples 8 and 9 or examples 12 and 13. As noted above, Additional examples 1 to 4 are not representative of the claimed subject matter because they do not contain any units according to instant formula 6, and therefore, the examples are not considered sufficient to establish that there are unexpected results associated with the presently claimed subject matter.
Moreover, Additional Examples 1 to 4, like instant examples 19 and 20, show a copolymer comprising a combination of four different diamine units which has expected intermediate thermal stability properties:
Instant examples 8 and 9, which are copolymers having two different diamine units (B2 and B3), have Td values of 455-456 and wtr values of 42.
Instant example 12, which is a copolymer having two different diamine units (B4 and B5), has a Td value of 470 and a wtr value of 49.
Instant examples 19 and 20, which are copolymers having four different diamine units (B2, B3, B4 and B5), have Td values 465 and 468, and wtr values of 44 and 48, which fall between the Td and wtr values of the exemplified copolymers having only B2 and B3 units (examples 8, 9), or only B4 and B5 units (examples 12, 13).
Note that Applicant has not provided information regarding the ratio of B2:B3 used to form the polyimides of additional examples 1-4. The Declaration (12/18/25, p 2) indicates that the additional examples were prepared in the same manner as examples 19 and 20 in the instant specification, however, instant examples 19 and 20 have different ratios of B2:B3. Because it is not clear which B2:B3 ratio was used in the additional examples, it is not clear which of the instant examples provide a meaningful comparison to Additional examples 1-4.
Applicant argues (p 9) that the additional experimental data shows a non-linear dependence of YI on molar ratio, and therefore the establish that the property profile would not have been predictable to a person of ordinary skill in the art. To the extent that it is possible to analyze the YI data of the additional examples without knowing the ratio of B2:B3, Table B appears to show a predictable trend: copolymers formed from diamine monomers B2, B3, B4 and B5 (examples 19, 20, AE1-4, AC1-4) have YI values ranging from 2.52 to 3.89, wherein the YI value depends on the ratio of B4:B5. Copolymers comprising all four diamine units have YI values between the YI values of copolymers having two of the diamine units, i.e., only monomers B2 and B3 (examples 8 and 9, which have YI values of 4.04 or 4.05) and copolymers have the other two diamine units, i.e., only monomers B4 and B5 (examples 11-14, which have YI values of 2.31 to 3.70, wherein the YI value depends on the ratio of B4:B5).
Therefore, for the reasons above and reasons which were also previously discussed in paragraphs 21-27 of the action mailed on 2/27/2026, Applicant has not provided data which establishes that copolymers comprising a combination of four monomers in ratios as in the instant examples exhibit a combination of properties which would have been unexpected. Applicant is further advised that in order to establish unexpected results, provided data must be commensurate in scope with the claimed subject matter. For at least the reason that Applicant has not provided any data for polyimides which fall within the scope of the present claims, Applicant’s data is not sufficient to establish unexpected results.
Applicant argues (pp 10-11) that the cited prior art discloses a large genus of possible diamine combinations, and one would not been directed toward the specific combination and claimed molar ratios with a reasonable expectation of achieving the improvement in properties demonstrated by Applicant’s examples. This argument is unpersuasive for at least the reason that Applicant has not provided any data for polyimides which fall within the scope of the present claims, and therefore, Applicant has not established that a simultaneous improvement in properties is achieved in the claimed subject matter. Moreover, the fact that Hasegawa discloses numerous types of diamine monomers which can be suitably selected to form a copolymer does not render any particular combination of two or more of Hasegawa’s disclosed diamine monomers less obvious. A reference is available for all that it teaches to a person of ordinary skill in the art. Merck & Co., Inc. v. Biocraft Laboratories, Inc. 874 F.2d 804, 807 (Fed. Cir. 1989).
Applicant argues (pp 11-12) that Hasegawa discloses intrinsic viscosity of a polyamic acid precursor, but does not disclose the molecular weight of a final polyimide copolymer. However, Hasegawa clearly associates a higher intrinsic viscosity and a higher molecular weight with improved film toughness, and, teaches that the specific disclosed CHTCA dianhydride monomer enables production of a high molecular weight precursor and a high molecular weight polyimide [0031]. Given the wide intrinsic viscosity range for the polyimide precursor disclosed by Hasegawa, and given the substantial chemical structure similarity between a polyimide precursor and the final polyimide polymer, there is reasonable basis to conclude that Hasegawa’s polyamic acid viscosity range corresponds to polyimide viscosity and molecular weight ranges which at least overlap the presently claimed ranges. For the reasons adequately set forth in the rejection of record, it would have been obvious to the person having ordinary skill in the art to have formed a polyamic acid precursor having any intrinsic viscosity within Hasegawa’s disclosed range of 0.5-3.8 dL/g, including an intrinsic viscosity which corresponds to a polyimide intrinsic viscosity and polyimide molecular weight within the presently claimed ranges, in order to ensure a high enough molecular weight associated with a desired film forming property and film toughness.
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 RACHEL KAHN whose telephone number is (571)270-7346. The examiner can normally be reached Monday to Friday, 8-5.
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, Randy Gulakowski can be reached at 571-272-1302. 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.
/RACHEL KAHN/ Primary Examiner, Art Unit 1766
Prosecution Insights