DETAILED ACTION
Introductory Notes
Any paragraph citation of the instant is in reference to the U.S. published patent application.
Specification
The amendment to the specification filed 9/4/2025 correcting errors related to 40°C and MJ·m3 is entered. The paragraph in question is [0013] of the PGPUB which is the fourth paragraph on page 3 of the original filed specification of 12/28/2022.
Claim Objections
Claim 3 and 6-8 are objected to because of the following informalities:
Regarding claim 3, following amendment to claim 2, it is recommended claim 3 be amended to be consistent with claims 2, 9, and 10 regarding ordering of the text “number average molecular weight”.
Regarding claim 8, following amendments to claims 6 and 7, it is recommended claim 8 be amended to be consistent with claims 6 and 7 and state “epoxide groups of the poly(glycidyl methacrylate)”.
Regarding claim 8, the claim is missing “the” in line 3 when referencing “amine-terminated diterminal functionalizedpoly(ethylene oxide)”.
Regarding claims 6-8, each of these claims is missing multiple hyphens in the phrase “amine-terminated” as used in the specification and claim 1.
Appropriate correction is required.
Claim Rejections - 35 USC § 112(a)
The following is a quotation of the first paragraph of 35 U.S.C. 112(a):
(a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.
The following is a quotation of the first paragraph of pre-AIA 35 U.S.C. 112:
The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor of carrying out his invention.
Claims 6 and 8-10 are rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, as failing to comply with the written description requirement. The claim(s) contains subject matter which was not described in the specification in such a way as to reasonably convey to one skilled in the relevant art that the inventor or a joint inventor, or for applications subject to pre-AIA 35 U.S.C. 112, the inventor(s), at the time the application was filed, had possession of the claimed invention.
Each of the claims 6, 8-10 has been amended to state “a molar ratio of epoxide groups … to … amine groups of the amine terminated diterminal …”. At issue is the number of amine groups is two for each the diterminal polymers, creating a base ratio of epoxide groups to amine groups for the monomers of 1:2. The specification states in paragraph [0010] “a molar ratio between epoxide and PEG or PEO of from 1:1 to 60:1” where a ratio of monomers is 1:1 when comparing epoxide with PEG or PEO and this interpretation requires that “PEG or PEO” of the specification be read as amine terminated diterminal functionalized. When considering amine groups, this upper end ratio of the specification becomes 60:2 or 30:1, thus claims 6 and 8 are not supported for at least this reason.
The remaining claims are rejected due to dependency.
Claim Rejections - 35 USC § 112(b)
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claims 6-8 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.
Each claim recites the limitation “a molar ratio of epoxide groups … to … amine groups of the amine terminated diterminal …”. It is unclear if this ratio is 1:1 or 1:2 when comparing the base monomers which include two amine terminals. The specification states in paragraph [0010] “a molar ratio between epoxide and PEG or PEO of from 1:1 to 60:1” where a ratio of monomers is 1:1 when comparing epoxide with PEG or PEO and this interpretation requires that “PEG or PEO” of the specification be read as amine terminated diterminal functionalized. When considering the amended amine groups (previously recited as base monomers), it is unclear if the upper end ratio of the specification is 60:1 or 60:2 due to the PEG or PEO being amine terminated diterminal.
The remaining claims are rejected due to dependency.
Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claims 1-10 and 12 are rejected under 35 U.S.C. 103 as being unpatentable over PAN (US 20180226679 A1) in view of CHEN ("Synthesis of solid–solid phase change material for thermal energy storage by crosslinking of polyethylene glycol with poly (glycidyl methacrylate)", Solar Energy 85.11 (2011): 2679-2685, supplied with the IDS of 12/28/2022) as evidenced by SIGMA (Product Specification for Poly(glycidyl methacrylate), Sigma-Aldrich).
Regarding claim 1, PAN discloses a solid polymer electrolyte (“solid polymer electrolytes” claim 1) comprising a comb-chain crosslinked network (“crosslinked network” claim 1) formed by reacting an epoxy containing polymer with an amine-terminated diterminal functionalized poly(ethylene glycol) or an amine-terminated diterminal functionalized poly(ethylene oxide) (“functionalized poly(ethylene glycol) or a functionalized poly(ethylene oxide)” claim 1; “poly(ethylene glycol)diamine” [0039]), in the presence of one or more lithium salts (“in the presence of a lithium or sodium salt or mixture of lithium and sodium salts” claim 1). PAN further discloses “an epoxy group at a distal end of one or more of the R groups” [0029] as well as Fig. 1B showing the use of epoxy groups.
PAN does not expressly teach the epoxy containing polymer is poly(glycidyl methacrylate).
CHEN discloses the use of poly (glycidyl methacrylate), or PGMA, and PEG to form a crosslinked copolymer (Abstract). In contrast to PAN, CHEN utilizes carboxyl PEG, or CPEG (Abstract), instead of the amine-terminated PEG of PAN. However, CHEN discloses there are “many epoxy groups in the molecular chains of poly (glycidyl methacrylate) (PGMA), which can easily react with various functional groups such as -OH, -COOH and -NH2 of other compounds to form new copolymers” (pg. 2/2680, col. 1, par. 3). As such there is significant overlap in the teachings of CHEN and PAN in regard to the functionalization of PEG. CHEN further discloses the crosslinked PEG/PGMA copolymer has “good heat resistant performance” (pg. 6/2684, col. 1, par. 1) due to “PGMA skeleton and the crosslinking structure restricts PEG molecular chains’ free movement at high temperature” (pg. 6/2684, col. 1, par. 2).
Before the effective filing date of the claimed invention, it would have been obvious to one of ordinary skill in the art to substitute the epoxy containing polymer PGMA of CHEN for the epoxy containing polymer of PAN because there are many epoxy groups in the chains of PGMA which can easily react with functional groups and form a skeleton for crosslinking.
Therefore, modified PAN discloses reacting poly(glycidyl methacrylate) (as taught by CHEN) with an amine-terminated diterminal functionalized poly(ethylene glycol) (as taught by PAN), in the presence of one or more lithium salts (as taught by PAN).
Regarding poly(glycidyl methacrylate) having 10 to 5000 epoxide groups, modified PAN discloses all the claim limitations as set forth above including the composition of the crosslinked copolymer to provide the required network structure, however modified PAN does not expressly teach the poly(glycidyl methacrylate) with 10 to 5000 epoxide groups. CHEN does provide illustrative Fig. 6 wherein a section of the network is shown and the number of links to PGMA is greater than ten.
Furthermore, as evidenced by SIGMA, PGMA may have a number average molecular weight of ca. 20,000. The molecular weight of PGMA is directly correlated to the number of epoxide groups because there is one epoxide group per monomer. The conversion factor for molecular weight to epoxide groups is therefore approximately 142 to 1 due to the molecular weight of the monomer C7H10O3. This conversion factor is noted in the instant in paragraph [0008] where the “or” is not two distinct choices, but instead a mathematical statement. Notably the instant utilizes the same math of molar mass polymer / 142 in [0023] which states “for a molar mass of 15,000 g mol-1 poly(glycidyl methacrylate), 106 epoxide groups are available for further crosslinking/functionalization”. Given this relationship, as evidenced by SIGMA, PGMA may have approximately 20,000 / 142 which corresponds to 141 epoxide groups, which is within the claimed range.
Furthermore, adjustment of the molecular weight of PGMA would have been considered a result effective variable by one having ordinary skill in the art at the time the invention was made. As such, without showing unexpected results, the molecular weight of PGMA cannot be considered critical. Accordingly, one of ordinary skill in the art at the time the invention was made would have optimized, by routine experimentation, the molecular weight of PGMA in modified PAN to obtain the desired network structure (In re Boesch, 617 F.2d. 272, 205 USPQ 215 (CCPA 1980)), since it has been held that where the general conditions of the claim are disclosed in the prior art, discovering the optimum or workable ranges involves only routine skill in the art (In re Aller, 105 USPQ 223).
Regarding claims 2 and 3, as discussed in the rejection of claim 1, modified PAN teaches PGMA with a molecular weight of approximately 20,000 which equates to 141 epoxide groups, which is within the claimed ranges.
Regarding claim 4, modified PAN discloses all the claim limitations as set forth above and PAN further discloses the poly(glycidyl methacrylate) is reacted with the amine-terminated diterminal functionalized poly(ethylene glycol) (“poly(ethylene glycol)diamine” [0039]).
Regarding claim 5, modified PAN discloses all the claim limitations as set forth above and PAN further discloses the poly(glycidyl methacrylate) is reacted with the amine-terminated diterminal functionalized poly(ethylene oxide) (“amine-terminated poly(ethyl oxide) (PEO)” [0033]).
Regarding claims 6, 7, and 8, modified PAN discloses all the claim limitations as set forth above and PAN further discloses a molar ratio between epoxide groups and amine groups of the amine-terminated diterminal functionalized PEG or PEO of from 2:1 to 10:1 (“octakis(3-glycidyloxypropyldimethylsiloxy)octasilsesquioxane (octa-POSS)” [0019] wherein there are eight epoxy groups in the POSS and Table 1 wherein the molar ratio of examples includes an example of POSS:PEG of 1:2 which correlates to an epoxide to PEG ratio of 8:2 or 4:1, within the claimed range regardless of the manner in which amine groups of amine-terminated diterminal is interpreted; furthermore, PAN teaches the ability to “tune the network structures in a large scale by changing the PEG polymer molecular weight and/or molar ratio” [0020] wherein molar ratio is what determines the claimed epoxide to amine ratio).
Regarding claims 9 and 10, modified PAN discloses all the claim limitations as set forth above and PAN further discloses the amine-terminated diterminal functionalized poly(ethylene glycol), has a number average molecular weight of from about 1,000 g/mol to about 6,000 g/mol (PAN provides examples in Table 1 with PEG4K and PEG6K).
Regarding claim 12, modified PAN discloses all the claim limitations as set forth above and PAN further discloses an overall ionic conductivity of the solid polymer electrolyte is 1.3 x 10-4 S cm-1 or greater (PAN Table 1 gives ionic conductivity values of 9.5 x 10-5 and 4.4 x 10-5 S/cm for two different samples wherein these values are at 30°C and notably higher than any sample in the instant at 25°C; and further “1.5×10-3 S/cm at 90°C” [0023]; while at 40°C is not reported in PAN, given the higher values at close to room temperature the values at 40°C can likewise be expected to be higher than the claimed value given modified PAN shares the underlying structure of the instant) and the solid polymer electrolyte has a toughness as measured at 25°C of greater than 0.1 MJ·m-3 (“mechanical properties … can be tuned by changing the cross-linked structures” [0003]; while modified PAN does not disclose toughness, PAN discloses “high modulus” in the Abstract as well as storage modulus tests at 90°C in Table 1 of 6.3 to 38.5 MPa; furthermore modified PAN shares the underlying structure of the instant and therefore shares similar properties such as toughness).
Response to Arguments
Regarding arguments toward the restriction, the restriction was deemed proper and final as discussed in the office action of 6/6/2025.
Regarding art-based rejections, applicant’s arguments with respect to claim 1 have been considered but are not persuasive. As discussed in the rejection of claim 1, the number of epoxide groups in PGMA is directly related to the molecular weight and as such the previous rejection of claim 2 from the claim set of 5/6/2025 is applicable. Furthermore, it is the PGMA of modified Pan, and not the POSS of Pan which reads on the claim and therefore arguments toward the eight reactive sites of a single POSS are moot for at least that reason. Notably, when considering total epoxides to amines in the network, PAN teaches similar ratios to that of the instant.
In response to applicant's argument that CHEN is nonanalogous art, it has been held that a prior art reference must either be in the field of the inventor’s endeavor or, if not, then be reasonably pertinent to the particular problem with which the inventor was concerned, in order to be relied upon as a basis for rejection of the claimed invention. See In re Oetiker, 977 F.2d 1443, 24 USPQ2d 1443 (Fed. Cir. 1992). In this case, each of PAN and CHEN utilize PEG to form a crosslinked copolymer (Abstract). Furthermore, CHEN discloses there are “many epoxy groups in the molecular chains of poly (glycidyl methacrylate) (PGMA), which can easily react with various functional groups such as -OH, -COOH and -NH2 of other compounds to form new copolymers” (pg. 2/2680, col. 1, par. 3). As such there is significant overlap in the teachings of CHEN and PAN in regard to crosslinking with functionalized PEG.
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.
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/T.L.M./Examiner, Art Unit 1721
/ALLISON BOURKE/Supervisory Patent Examiner, Art Unit 1721
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