DETAILED ACTION
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 .
Status of Claims
Applicant’s amendment and arguments, filed 11/27/2025, have been fully considered. Claim(s) 1, 8, 10, 11, 13, and 14 is/are amended; claim(s) 3, 6, 9, 12, and 15–18 stand(s) as originally or previously presented; claim(s) 2, 4, 5, and 7 is/are canceled; and claim 19 is added without entering new matter. Examiner affirms that the original disclosure provides adequate support for the amendment.
Upon considering said amendment and arguments, the previous claim objections set forth in the Office Action mailed 08/28/2025 has/have been withdrawn. However, the pending 35 U.S.C. 103 rejection has been maintained and altered as necessitated by Applicant’s amendment, as set forth below. Additionally, Applicant’s amendment necessitated the new claim objection and 35 U.S.C. 112(b) rejection.
Claim Objections
Claim 19 is objected to for the following informality: in line 2, “100 wt% of composition” should read “100 wt% of the composition” for proper grammar. Appropriate correction is required.
Claim Rejections - 35 USC § 112
The text forming the basis for the rejection under 35 U.S.C. 112(b) may be found in a prior Office Action.
Claims 1, 3, 6, and 8–19 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.
A broad range or limitation together with a narrow range or limitation that falls within the broad range or limitation (in the same claim) may be considered indefinite if the resulting claim does not clearly set forth the metes and bounds of the patent protection desired. See MPEP 2173.05(c). In this case, claim 1 recites the broad recitation “a compound represented by Chemical Formula 1 … wherein, in Chemical Formula 1, X is F, and n is an integer of 1-6” (lines 6–11), and the claim also recites “wherein the compound represented by Chemical Formula 1 is at least one selected from the group consisting of fluorobenzene, difluorobenzene, trifluorobenzene, and tetrafluorobenzene” (lines 21–23), which is the narrower statement of the range/limitation (by omitting pentafluorobenzene and hexafluorobenzene, i.e., n = 5 or 6). The claim is considered indefinite because there is a question or doubt as to whether the feature introduced by such narrower language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claims.
The spec.’s p. 3, lines 14–21, details a compound of Chemical Formula 1, where X is at least one halogen selected from the group consisting of F, Cl, Br, and I, and n is an integer of 1–6. Although such is exemplary (see “According to the first embodiment”, p. 3, line 11), claim 1 narrows X to F and appears to further limit the compound to fluorobenzene, difluorobenzene, trifluorobenzene, and tetrafluorobenzene. Thus, for this Office Action (and the sake of compact prosecution) claim 1 will be interpreted to require an “n” satisfying a value consistent with at least one of fluorobenzene (1), difluorobenzene (2), trifluorobenzene (3), or tetrafluorobenzene (4), which appears consistent with the intended scope.
Claim 19 recites “an amount of the crosslinking agent” in line 2. In depending from claim 1, which does not require a crosslinked composition, it is unclear which compound “the crosslinking agent” references.
Table 1 (p. 41) details a “content of crosslinking agent” and correlates this agent to the polymerizable compound (see matching wt%s in exs. and comp. exs. 1–3 on pp. 33–38 compared to Table 1; see also, e.g., p. 18, lines 14–16). Thus, for this Office Action claim 19 will be interpreted to require, as “an amount of the crosslinking agent”, an amount of the polymerizable compound of 3–7 wt% based on 100 wt% of the composition.
The remaining dependent claims fail to correct these deficiencies and are rejected likewise. Appropriate correction is required.
Claim Rejections - 35 USC § 103
The text forming the basis for the rejection under 35 U.S.C. 103 may be found in a prior Office Action.
Claim(s) 1, 3, and 8–19 is/are rejected under 35 U.S.C. 103 as being unpatentable over Yu et al. (US 20110195314 A1) (Yu) in view of Deguchi et al. (US 20060166091 A1) (Deguchi).
Regarding claims 1, 3, 8–11, and 14–16, Yu discloses a lithium secondary battery comprising a negative electrode, a positive electrode, a separator interposed between the negative and positive electrodes, and a gel polymer electrolyte formed by polymerizing a composition for a gel polymer electrolyte (e.g., Ex. 1, ¶ 0069–0077; see also composition formed when mixing composition for gel electrolyte with initiator, e.g., ¶ 0052), the composition comprising a lithium salt (LiPF6, Ex. 1, ¶ 0072); a non-aqueous organic solvent (ethylene carbonate (EC) and ethyl methyl carbonate (EMC), Ex. 1, ¶ 0072); a polymerization initiator (t-butyl peroxy-2-ethylhexanoate, Ex. 1, ¶ 0070); and at least one polymerizable compound of trimethylolpropane triacrylate (Ex. 1, ¶ 0072).
Yu further discloses that the composition may further include additives known in the art (¶ 0062) but fails to explicitly disclose the recited Formula 1 compound of fluorobenzene, difluorobenzene, trifluorobenzene, and/or tetrafluorobenzene at ≥ 10 vol% based on a total volume of the organic solvent and the Formula 1 compound.
Deguchi, in teaching a battery (Abstract), teaches an electrolyte containing a non-aqueous solvent and a fluorinated, aromatic compound of most preferably fluorobenzene (e.g., Abstract, ¶ 0035, and working exs.)—i.e., the Formula-1 compound, where X is F, and n is 1—as well as a positive electrode comprising a nickel-containing lithium oxide (e.g., ¶ 0011 and exs.). Deguchi teaches that the fluorinated compound adsorbs to the nickel-based positive electrode material to form a film that inhibits side reactions between the electrolyte and positive active material in high-temperature environments (¶ 0018, 0019), improving cycle characteristics (¶ 0018). Deguchi further teaches that the fluorinated compound preferably constitutes 5–20 parts by weight of the solvent (¶ 0036)—yielding a weight ratio of the fluorinated compound based on the total weight of this compound and the solvent of 4.76–16.67%—because this range allows the film to form without making the film too thick, which can inhibit (dis)charging (¶ 0036).
Deguchi and Yu are analogous prior art to the claimed invention because they pertain to the same field of endeavor, namely non-aqueous battery electrolytes.
As Yu allows the positive active material to be a lithium nickel oxide (¶ 0032), it would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to incorporate fluorobenzene as a Formula-1 compound into Yu’s electrolyte at 4.76–16.67 wt% based on a total weight of the solvent and fluorobenzene, as well as employ a lithium nickel oxide positive active material with the reasonable expectation of achieving a successful electrolyte composition and active material capable of inhibiting electrolytic side reactions to improve cycling characteristics, as taught by Deguchi. Moreover, to ensure that the fluorobenzene film is thick enough to achieve this effect without making the film too thick and inhibiting (dis)charging, all while accounting for proper solubility from the solvent’s content, it would have been obvious to arrive at the recited vol% by routinely optimizing the fluorobenzene’s content, including within the apparent overlap, which, even when converting from weight content to volumetric content, seems to still significantly overlap the recited ≥ 10 vol% given organic electrolyte solvents and additives’ known densities close to 1 g/mL (MPEP 2144.05 (II)).
It is submitted that the above disclosure further reads on the following:
(claim 3) the fluorobenzene’s 4.76–16.67 wt% appears to significantly overlap and appear optimizable to achieve the recited 10–30 vol% when balancing effects based on the fluorobenzene film’s thickness/content (per claim 1);
(claims 8–11) the non-aqueous organic solvent comprises at least one carbonate solvent of a mixed solvent of linear carbonate of ethyl methyl carbonate and a cyclic carbonate of ethylene carbonate (EMC and EC, respectively, Yu’s Ex. 1, ¶ 0072);
(claim 14) the lithium salt comprises Li+, as a cation, and PF6- as an anion (Yu, Ex. 1, ¶ 0072).
Regarding claims 12 and 13, modified Yu discloses the composition for a gel polymer electrolyte according to claim 1.
As noted above, Yu exemplarily discloses a mixed solvent including a cyclic carbonate (mixed solvent with EC, Ex. 1, ¶ 0072), as well as the ability to include esters such as methyl acetate as equivalent solvents (¶ 0060), but fails to explicitly disclose such in Ex. 1.
As Yu recognizes linear and cyclic carbonates such as EMC and EC, respectively, as well as esters such as methyl acetate as equivalent solvents, it would have been obvious to one of ordinary skill in the art, before the claimed invention’s effective filing date, to routinely incorporate a mixture of these three compounds—so that the solvent would comprise a mixed solvent of a cyclic carbonate (EC) with a linear ester (methyl acetate)—with a reasonable expectation of forming a successful solvent mixture and polymer electrolyte (MPEP 2144.06 (I) and 2143 (A.)).
Regarding claims 17 and 18, modified Yu discloses the composition for a gel polymer electrolyte according to claim 1.
As noted above, Yu exemplarily discloses trimethylolpropane triacrylate (Ex. 1, ¶ 0072) yet, while further disclosing that 4-vinylcyclohexene dioxide—i.e., vinylcyclohexene dioxide—and trimethylolpropane ethoxylate triacrylate are equally suitable polymerizable monomers (¶ 0057), fails to explicitly disclose either compound in Ex. 1.
As Yu recognizes trimethylolpropane triacrylate, 4-vinylcyclohexene dioxide, and trimethylolpropane ethoxylate triacrylate as equivalent polymerizable compounds, it would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to routinely substitute trimethylolpropane triacrylate with 4-vinylcyclohexene dioxide or trimethylolpropane ethoxylate triacrylate with a reasonable expectation of forming a successful polymer electrolyte (MPEP 2144.06 (II) and 2143 (B.)).
Regarding claim 19, modified Yu discloses the composition for a gel polymer electrolyte according to claim 1.
Yu further exemplifies 5 parts trimethylolpropane triacrylate, i.e., polymerizable compound (and treated as crosslinking agent), per 100 parts electrolyte (Ex. 1, ¶ 0072) but appears to fail to specify this value in terms of the whole composition and, thus, 3–7 wt% based on 100 wt% composition. However, Yu generally discloses that the polymer electrolyte monomer (e.g., trimethylolpropane triacrylate) may constitute 0.01–10 parts by weight based on 100 parts by weight of the electrolyte salt/solvent, disclosing that > 10 parts by weight excessively gels the composition and yields high resistance, while < 0.01 parts by weight prevents gelation from properly occurring (¶ 0058). Meanwhile, the polymerization initiator may be included at 0.01–5 parts by weight per 100 parts electrolyte because > 5 parts yields either too early gelation or diminished battery performance, whereas < 0.01 parts inhibits gelation from occurring properly (¶ 0040). Moreover, the skilled artisan would recognize that enough lithium salt must be present for Li+ conductivity, while enough solvent must be present to properly dissolve the salt and auxiliary components without detracting from the other components’ effects. To balance all these effects, then, it would have been obvious to arrive at the recited range by routinely optimizing the polymerizable compound/crosslinker’s wt% based on the whole composition (MPEP 2144.05 (II)).
Claim(s) 6 is/are rejected under 35 U.S.C. 103 as being unpatentable over Yu et al. (US 20110195314 A1) (Yu) in view of Deguchi et al. (US 20060166091 A1) (Deguchi), as applied to claim 1, further in view of Lee et al. (US 20180166743 A1) (Lee).
Regarding claim 6, modified Yu discloses the composition for a gel polymer electrolyte according to claim 1 but is silent to the polymerizable compound’s molecular weight and, thus, fails to explicitly disclose a weight-average MW of 300–100,000 g/mol.
Lee, in teaching a gel electrolyte (e.g., ¶ 0223) comprising a polymerizable compound such as trimethylolpropane triacrylate (¶ 0080, 0081), teaches that the polymerizable compound preferably exhibits a weight-average MW of, e.g., 200~500 Daltons because such a range allows the compound to be easily injectable or soluble in a solvent (¶ 0080).
Lee is analogous prior art to the claimed invention because they pertain to the same field of endeavor, namely battery gel electrolytes.
It would have been obvious to one of ordinary skill in the art, before the claimed invention's effective filing date, that modified Yu’s polymerizable compound such as TMPTA must necessarily be incorporated with some molecular weight, and, as demonstrated by Lee, the skilled artisan would find it obvious to incorporate the polymer with a weight-average MW of, e.g., 200~500 Daltons, i.e., 200~500 g/mol, and routinely select within the overlap of 300~500 g/mol with a reasonable expectation of selecting a suitable MW for solubility (MPEP 2144.05 (I)).
Response to Arguments
Applicant’s arguments with respect to claim 1 have been fully considered but are unpersuasive.
Applicant argues that one skilled in the art would not seek to incorporate Deguchi’s fluorobenzene into Yu’s polymer electrolyte because Deguchi’s electrolyte is completely liquid and, thus, when incorporated into Yu’s electrolyte, would be locked and, therefore, unable to achieve the intended function of passivating the NiO cathode material. Examiner respectfully disagrees at least because Yu employs a liquid electrolyte (via solution in, e.g., Ex. 1; see also ¶ 0028) within the polymer and, as discussed above, discloses that the composition may further include known additives (¶ 0062). At minimum, then, it seems that the skilled artisan would have reasonably expected to achieve a successful electrolyte composition by incorporating Deguchi’s fluorobenzene as a known additive. Further, although not explicitly exemplified, Yu allows a) the composition to contact a separator or an electrode (¶ 0050), b) the electrolyte monomer and initiator to be in the cathode (¶ 0051), and c) the initiator to dissolve/disperse or be contacted by the monomer included in the liquid electrolyte (¶ 0037). Thus, Yu seems capable of affording the needed electrostatic proximity to form Deguchi’s NiO cathode film.
Applicant again argues that the Formula 1 compound generally reduces radical content to mitigate electrolyte decomposition. Examiner respectfully notes that Deguchi incorporates the fluorobenzene to inhibit side reactions between the electrolyte and positive active material in high-temperature environments (¶ 0019), which otherwise highly degrades cycle characteristics (¶ 0007). Thus, based on Deguchi, it appears that one skilled in the art would have expected similarly mitigated electrolyte decomposition by adding fluorobenzene. Alternatively, such effects are unclaimed, and Applicant’s recognizing another advantage that would flow naturally from following the prior art’s suggestions cannot be the basis for patentability when the differences would otherwise be obvious (MPEP 2145 (II)).
Assuming, arguendo, that the results were both unexpected and superior, Examiner respectfully reiterates that the results are incommensurate with claim 1’s scope at least as follows:
Claim 1 allows the Formula 1 compound to constitute ≥ 10 vol% based on a total volume of the solvent and the Formula 1 compound, but Table 1 only supports 10–20%; it is unclear if such results would occur at, e.g., 80 vol% Formula 1 compound.
Claim 1 allows the lithium salt to constitute any concentration, but Table 1 only supports 1 M; it is unclear if such results would occur at, e.g., 2 M salt.
Claim 1 allows the initiator to constitute any weight content, but Table 1 only supports 0.04 wt%; it is unclear if such results would occur for, e.g., 10 wt%.
Claim 1 allows the polymerizable compound/crosslinker to constitute any weight content, but Table 1 only supports 3–7 wt%; it is unclear if such results would occur at, e.g., 10% or 15%.
Claim 1 is to a composition for a gel polymer electrolyte, but Test Ex. 3’s nail-penetration results stem from incorporating the composition, once polymerized, into a lithium secondary battery including a negative electrode, positive electrode, and separator.
Thus, per MPEP 716.02(d), this argument is further unpersuasive.
Conclusion
The cited art made of record but not relied upon is considered pertinent to Applicant’s disclosure:
US 20190237823 A1: battery liquid electrolyte with trifluorobenzene constituting 1–10 wt%.
US 20190148773 A1: battery liquid electrolyte that may include fluorobenzene at 0.1–5 wt%.
WO 2019108019 A1 (citation to English equivalent US 20200251776 A1): battery polymer electrolyte with benzene compound that may be halogen-substituted.
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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/J.S.M./Examiner, Art Unit 1751
/JONATHAN G LEONG/Supervisory Patent Examiner, Art Unit 1751 2/13/2026