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 1-20 are pending as amended on 12/17/2025.
Election/Restrictions
Applicant’s election without traverse of Group II (claims 4-18) in the reply filed on 9/11/2025 is acknowledged. Claims 1-3 and 19-20 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim.
Applicant’s further election without traverse of species b (wherein the polyimide oligomer is formed from dimer diamine and BPADA as in instant example 7) in the reply filed on 9/11/2025 is acknowledged. Claim 17 is withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected species, there being no allowable generic or linking claim.
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 4-16 and 18 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 4 depends from claim 1 (i.e., requires preparing the resin of claim 1). Claim 1 recites a molecular formula of a benzoxazine resin which is unclear for the reasons explained below, thereby rendering the scope of claim 4 unclear:
The formula recited in claim 1, including the definitions of the variables, is copied below:
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The formula contains a divalent “X1” group which is defined as “an alkyl or/and alkoxy containing a long chain structure in main chain or side chain;”. It is not clear how to interpret the definition of X1, because the X1 group in the recited formula is a divalent group, yet X1 is defined as “alkyl” and/or “alkoxy,” which are terms for monovalent groups. Furthermore, the language within the definition of X1 is confusing and seems to be missing word(s), making it challenging to interpret what structure is intended to be encompassed by the definition of X1. For examination purposes, X1 has been interpreted as at least encompassing structure derived from dimer diamine and linear alkylene diamines.
It is also not clear how to interpret the definition of X2, because the X2 group in the formula above is a divalent group, yet “alkyl” and “alkoxy” are terms for monovalent groups.
Claims 5-16 and 18 are rejected for the same reasons set forth above, because they depend on the rejected base claim, and they fail to correct the issue.
Additionally:
Claim 8 further limits a number of carbon atoms in “the alkyl and the cycloalkyl…” There is insufficient antecedent basis for this limitation in the claim: it is not clear whether “the alkyl” and “the cycloalkyl” recited in claim 8 refers to alkyl and cycloalkyl groups recited within the definitions of R groups, or, within the definition of X1, or, within the definition of X2.
Claim 10 depends from claim 5 and further limits “the reaction.” There is insufficient antecedent basis for this limitation in the claim: it is not clear whether “the reaction” recited in claim 10 refers to a reaction between dianhydride and diamine to form the polyimide oligomer recited in claim 5, or, refers to the reaction of polyimide oligomer with aldehyde and phenol as recited in claim 4. For examination purposes, since claim 10 depends from claim 5, “the reaction” recited in claim 10 has been interpreted as referring to the reaction of dianhydride and dibasic primary amine recited in claim 5.
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claims 5, 15 and 16 are rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends.
Claims 5 and 16 further limit the polyimide oligomer component of claim 4, and permit the dibasic primary amine reactant to be a mixture which includes an aromatic diamine. However, claim 4 requires preparing a benzoxazine resin of claim 1. The only moieties derived from a diamine in the benzoxazine resin formula of claim 1 are X1 moieties, and the definition of X1 does not permit an aromatic group. Because the benzoxazine resin formula recited in claim 1 excludes any structure derived from an aromatic diamine, claims 5 and 16 fail to properly further limit claim 4.
Claim 15 depends from claim 5 and further limits the dianhydride reactant to a specific group of dianhydrides, including biphenyltetracarboxylic dianhydride (BPDA), hexafluoroisopropylidene)diphthalic anhydride (6FDA), and benzenetetracarboxylic dianhydride (PMDA). However, claim 5 requires preparing a benzoxazine resin of claim 1. The only moieties derived from a dianhydride in the benzoxazine resin formula of claim 1 must contain two benzene rings (which excludes units derived from PMDA), and must contain an X2 group. The definition of X2 does not include a single bond (which excludes a unit derived from BPDA) or haloalkyl (which excludes a unit derived from 6FDA). Because the benzoxazine resin formula recited in claim 1 excludes any structure derived from BPDA, 6FDA or PMDA, claims 15 fails to properly further limit the subject matter of the claim upon which it depends.
Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
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.
Claim(s) 4-16 and 18 is/are rejected under 35 U.S.C. 103 as being unpatentable over Mizori et al (WO 2020/215027).
As to claims 4-8, 15 and 16, Mizori discloses a curable polyimide having the following structure [0018]:
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Wherein X is a curable moiety [0019], such as benzoxazine [0020].
Mizori discloses a method comprising functionalizing an amine-terminated polyimide by reacting terminal amine groups with a phenolic moiety and formaldehyde, which converts terminal amine groups to benzoxazine groups [0028]. Mizori exemplifies a process of producing a benzoxazine-terminated polyimide wherein the phenolic moiety reacted with the amine-terminated polyimide is phenol (corresponding to the presently recited monofunctional phenolic compound recited in claims 4, 7 and 8, and providing “R” groups in the claim 1 formula which are H), and the formaldehyde is paraformaldehyde (meeting instant claim 6) [0210].
As to the recitation of an “oligomer” and as to “n” recited in claim 1:
Mizori teaches that “n” in formula I is 0 to 100 [0019], and, there are two dianhydride-diamine moieties outside Mizori’s repeating unit bracket. Therefore, Mizori’s curable polyimide formula has a number of dianhydride-diamine repeating units within a range of 2 to 102. The formula recited in claim 1 has a number of dianhydride-diamine repeating units ranging from 1 to 150 (based on the definition “n” in claim 1). Given that the number of dianhydride-diamine repeating units in Mizori’s curable polyimide falls within the range of repeating units of the resin in claim 1, the amine-terminated polyimide reactant disclosed by Mizori must have a formula such that instant “n” is satisfied, and, must be considered an “oligomer” as presently recited.
As to instant X2:
Mizori names several suitable dianhydrides which provide “Q” in [0027], including 4,4’-oxydiphthalic anhydride (“ODPA,” recited in instant claim 15 and corresponding to “ether” as X2), 3,3’,4,4’-benzophenonetetracarboxylic anhydride (“BTDA,” recited in instant claim 15 and corresponding to “carbonyl” as X2), 4,4’-bisphenol A diphthalic anhydride (“BPADA,” recited in instant claim 15, corresponding to ether and alkyl as X2, and, corresponding to the dianhydride unit within the elected species). See also Mizori’s example 3 [0210], wherein BPADA is utilized as the dianhydride reactant.
As to instant X1:
Mizori names several suitable diamines which provide “R” in [0026], including several which contain an alkylene long chain structure in the main chain and therefore have moieties meeting instant X1 (e.g., 1,10-diaminodecane, 1,12-diaminododecane, 1,7-diaminoheptane), and, also including dimer diamine and hydrogenated dimer diamine, which provide moieties meeting instant X1 by providing an alkylene long chain structure in the main chain and a flexible long alkyl side chain (further meeting instant claims 5 and 16, and, corresponding to the diamine unit within the elected species). See also Mizori’s example 4 [0215] wherein dimer diamine is utilized as a diamine reactant.
Arriving at a method as presently recited in claims 4 and 15 requires selection of a long chain alkylene diamine from Mizori’s list in [0026] and selection of ODPA, BTDA or BPADA from Mizori’s list in [0027]. (Arriving at the elected species requires selection of dimer diamine as the diamine, and selection of BPADA as the dianhydride.) When preparing a polyimide from a diamine and dianhydride, the person having ordinary skill in the art would have recognized that the properties of the obtained polymer depend on the polymer chemical structure, and so would have been motivated to select appropriate diamine and dianhydride monomers from disclosed lists thereof in order to obtain an appropriate polymer structure, corresponding to desired properties for an intended application. Therefore, when preparing curable polyimide by reaction of an amine-capped polyimide oligomer with phenol and paraformaldehyde, as disclosed by Mizori, it would have been obvious to the person having ordinary skill in the art to have selected any appropriate dianhydride from Mizori’s list in [0027] (e.g., including ODPA, BTDA or the exemplified BPADA) and any appropriate diamine from Mizori’s list in [0026] (e.g., including 1,10-diaminodecane, 1,12-diaminododecane, 1,7-diaminoheptane, or the exemplified dimer diamine) for the synthesis of the polyimide, thereby arriving at the presently claimed subject matter. Case law has established that it is prima facie obvious to choose from a finite number of identified, predictable solutions with a reasonable expectation of success. KSR Int'l Co. v. Teleflex, Inc., 550 U.S. 398 (2007). MPEP 2143, rationale (E).
As to claim 9, Mizori suggests a method according to claim 4, as set forth above. Mizori exemplifies a process [0210] wherein amine-terminated polyimide is reacted with 0.12 mol phenol and 0.24 mol paraformaldehyde. Mizori teaches that the 0.12 mol of phenol is “20% excess,” which would mean that there is 0.10 mol of the amine-terminated polyimide. Therefore, Mizori exemplifies a ratio of polyimide to aldehyde to phenol of 0.10:0.24:0.12, which is equivalent to 1.0:2.4:1.2, which falls within the claimed range.
As to claim 11, Mizori suggests a method according to claim 4, as set forth above. Mizori exemplifies performing the reaction between amine-terminated polyimide, phenol and formaldehyde by refluxing in anisole (reflux temperature of 155 C) for 1 hour [0210], which falls within the presently claimed ranges of 60-180 C for 0.5-10h.
As to claim 18, Mizori suggests a method according to claim 4, as set forth above. Mizori teaches an average molecular weight of 25,000 to 50,000 Da [0019], which falls within the claimed range.
As to claim 10, Mizori suggests a method according to claim 4, as set forth above. Instant claim 4 is a method claim, and requires a step of subjecting a polyimide oligomer, an aldehyde and a phenolic compound to reaction. Claim 5 depends from claim 4, and further limits the polyimide oligomer by requiring it to be “a reaction product of a …dianhydride and a dibasic primary amine…” The method of claim 5 does not recite performing steps of reacting a dianhydride and a diamine to produce the recited polyimide oligomer. Rather, claim 5 recites a polyimide oligomer which has a structure implied by a reaction of dianhydride and diamine. In other words, claim 5 further limits the polyimide oligomer recited in claim 4 by defining the structure thereof with a product-by-process limitation.
Claim 10 depends from claim 5 and further limits the solvent in which the polyimide-forming reaction recited in claim 5 (i.e., the reaction of dianhydride and diamine to produce the polyimide oligomer) is performed. Mizori teaches anisole as a solvent, which is not one of the solvents recited in claim 10. However, case law has established that the patentability of a product-by-process is determined by the patentability of the product itself, i.e., that the patentability of a product does not depend upon its method of production (MPEP 2113). The process limitations are only given consideration regarding patentability if there is criticality to the structure implied by the steps of the process. No such criticality has been demonstrated to the presently recited use of a solvent as recited in claim 10 to the structure of the ultimately obtained polyimide oligomer. The solvent utilized in the reaction of dianhydride and diamine to form a polyimide product does not form part of the structure of the polyimide product. As such, it is the examiner’s position that the polyimide oligomer (formed by reaction of dianhydride and diamine) suggested by Mizori meets the polyimide oligomer reaction product recited in claim 10, notwithstanding any difference in the solvent utilized for the formation of the polyimide oligomer.
As to claims 12 and 14, Mizori suggests a method according to claim 10, as set forth above. Claim 12 further limits the polyimide oligomer by requiring an oligomer which “is prepared” though four steps (S1)-(S4). Claim 12 does not further limit claim 10 by requiring preparing polyimide oligomer by performing steps according to (S1)-(S4). Rather, claim 12 recites a polyimide oligomer product defined by the method in which it is produced.
Mizori discloses forming a polyimide oligomer by dissolving diamine in solvent to obtain a first mixture, adding the dianhydride, heating for 1 hour to completely remove water and form an amine-terminated polyimide oligomer [0215]. Mizori fails to specifically teach using nitrogen atmosphere as recited in (S1), fails to teach that the addition of dianhydride is “stepwise” as in (S2), fails to teach a temperature/time for (S3) within the ranges recited in claim 14, and fails to teach an addition of water-carrying agent as recited in step (S4).
However, as set forth above, case law has established that the patentability of a product-by-process is determined by the patentability of the product itself, i.e., that the patentability of a product does not depend upon its method of production (MPEP 2113). The process limitations are only given consideration regarding patentability if there is criticality to the structure implied by the steps of the process. No such criticality has been demonstrated to the presently recited use of nitrogen, the presently recited “stepwise” addition of dianhydride, nor the presently recited addition of an unspecified water-carrying agent to the structure of the ultimately obtained polyimide oligomer. Note that claim 12 does not limit the nitrogen protection to any particular purity of, does not limit the speed of stepwise dianhydride addition, and does not limit the “water-carrying agent” for imidization to any particular substance. As such, it is the examiner’s position that the polyimide oligomer suggested by Mizori meets the polyimide oligomer reaction product recited in claims 12 and 14, notwithstanding any difference in the conditions utilized for the formation of the polyimide oligomer.
As to claim 13, Mizori suggests a method according to claim 12, as set forth above. Mizori discloses that the diamine is provided in slight excess to the dianhydride, and discloses a ratio of 1.05:1 [0025], which falls within the range recited in claim 13.
Double Patenting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claims 4 is provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-2 of copending Application No. 18/091307 (reference application). The claims at issue are not identical, because the copending claims require a composition which contains a resin component in addition a benzoxazine resin according to the instant claims, and, the copending claims are product-by-process claims rather than process claims. However, the instant claims are not patentably distinct from the copending claims:
As to claim 4, a benzoxazine having the same formula as presently recited is recited in claim 2 of the copending claims. Copending claim 2 depends from copending claim 1, which contains the presently recited method steps (see lines 4-5 of copending claim 1). This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Citation of Pertinent Prior Art
The following prior art is made of record. Rejections citing the following references are not being made at this time, as such rejections would be cumulative to the rejection over Mizori above. However, the references below are considered pertinent to applicant's disclosure.
Kyran et al (WO 2021/198793) discloses:
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[0029], wherein the benzoxazine crosslinkable units are formed by reacting an amine-terminated thermoplastic polymer (TP) with formaldehyde and phenol [0030], and wherein TP can be a polyimide backbone prepared from reaction of diamine and dianhydride [0022]. Kyran names several dianhydrides encompassed by the instant formula, including BPADA [0024] as well as several aliphatic diamines having flexible alkyl chains [0025].
Kawahara et al (WO 2019/189467) discloses a benzoxazine compound that can be obtained by reacting a dianhydride and diamines including a dimer diamine to obtain a reaction product having amino groups at both ends, and then reacting the reaction product with phenol and paraformaldehyde [translation 0073-4].
Qiu et al (CN 114805802A) discloses:
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obtained by reaction of amine-terminated polyimide, phenol and paraformaldehyde [0030]:
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, wherein named dianhydrides include BPADA (translation [0019]) and named diamines include flexible aliphatic (e.g., hexamethylenediamine) (translation [0020]).
Susa et al (Understanding the Effect of the Dianhydride Structure on the Properties of Semiaromatic Polyimides Containing a Biobased Fatty Diamine, ACS Sustainable Chem. Eng. 2018, 6, 668−678) shows how the thermal, mechanical and optical properties of a polyimide prepared from dimer diamine as the diamine component change, depending on the selection of the dianhydride structure. BPADA is included among the four compared dianhydride structures.
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Conclusion
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.
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/RACHEL KAHN/Primary Examiner, Art Unit 1766