DETAILED ACTION
Application 18/268,293, “A POLYMER ELECTROLYTE”, was filed with the USPTO on 6/19/2023 and has a foreign priority document of EP20217308.4 filed on 12/24/2020.
This office action is in response to communication filed on 6/19/2023.
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 .
Priority
Acknowledgment is made of applicant’s claim for foreign priority under 35 U.S.C. 119 (a)-(d). The certified copy has been filed in parent Application No. 18/268,293, filed on 6/19/2023.
Information Disclosure Statement
The information disclosure statements (IDS) submitted on 6/19/2023, 6/26/2024 and 8/12/2025 are in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statements are being considered by the examiner.
Specification
Applicant is reminded of the proper language and format for an abstract of the disclosure.
The abstract should be in narrative form and generally limited to a single paragraph on a separate sheet within the range of 50 to 150 words in length. The abstract should describe the disclosure sufficiently to assist readers in deciding whether there is a need for consulting the full patent text for details.
The language should be clear and concise and should not repeat information given in the title. It should avoid using phrases which can be implied, such as, “The disclosure concerns,” “The disclosure defined by this invention,” “The disclosure describes,” etc. In addition, the form and legal phraseology often used in patent claims, such as “means” and “said,” should be avoided.
The abstract of the disclosure is objected to because it contains legal phraseology (see “said polymer (P)” in line 4 and “Said at least one polysiloxane” in line 7). A corrected abstract of the disclosure is required and must be presented on a separate sheet, apart from any other text. See MPEP § 608.01(b).
The disclosure is objected to because of the following informalities:
In line 32, page 5, “improvise” should read “improves”.
Appropriate correction is required.
The disclosure is objected to because line 24 on page 13 and line 22 on page 17 each contains an embedded hyperlink and/or other form of browser-executable code. Applicant is required to delete the embedded hyperlink and/or other form of browser-executable code; references to websites should be limited to the top-level domain name without any prefix such as http:// or other browser-executable code. See MPEP § 608.01.
Alkox® CP-A (line 25 on page 9):
The use of the term Alkox® CP-A, which is a trade name or a mark used in commerce, has been noted in this application. The term should be accompanied by the generic terminology; furthermore the term should be capitalized wherever it appears or, where appropriate, include a proper symbol indicating use in commerce such as ™, SM , or ® following the term.
Although the use of trade names and marks used in commerce (i.e., trademarks, service marks, certification marks, and collective marks) are permissible in patent applications, the proprietary nature of the marks should be respected and every effort made to prevent their use in any manner which might adversely affect their validity as commercial marks.
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 11-15, 17 and 20 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 16-22 and 29 of copending Application No. 18/268,339 (hereinafter 339’). Although the claims at issue are not identical, they are not patentably distinct from each other because:
Regarding claim 11, 339’ teaches a polymer electrolyte suitable for use in lithium-ion secondary batteries being obtained by reaction between:
i. at least one polyether polymer [hereinafter polymer (P)], said polymer (P) comprising:
a) at least 70.0 % by moles of oxyethylene units (EO);
b) from 0.0 to 10.0 % by moles of oxypropylene units (PO); and
c) from 1.00 to 4.0 % by moles of recurring units derived from at least one monomer [hereinafter, monomer (M)] of general formula (I) or of general formula (II):
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wherein
- each of R1 and R2, equal to or different from each other and at each occurrence, is C1-6 alkanediyl wherein said C1-6 alkanediyl, is optionally substituted with one or more substituents selected from halide, C1-4 alkyl, C3-6 cycloalkyl, CF3, and OR8, and wherein each of R8, equal to or different from each other and at each occurrence, is independently selected from the group hydrogen and C1-4 alkyl; n is an integer 0 or 1 or 2;
- each of X is a leaving group selected from the group consisting of halide, trifluoromethanesulfonate, nonafluorobutanesulfonate, p-toluenesulfonate and methanesulfonate;
and
ii. at least one polysiloxane compound having the formula (III)
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wherein
- each of R3, R4, R5, R6 and R7, equal to or different from each other and at each occurrence, is independently selected from the group consisting of C1-6 alkyl, C3-6 cycloalkyl, aryl, C1-6 alkoxy, and heterocyclyl, wherein said C1-6 alkyl, C3-6 cycloalkyl, aryl, C1-6 alkoxy, heterocyclyl are optionally substituted with one or more substituents selected from halide, C1-4 alkyl, C3-6 cycloalkyl, CF3, and OR9, and wherein each of R9, equal to or different from each other and at each occurrence, is independently selected from the group consisting of hydrogen, C1-4 alkyl, and a hydroxyl protecting group,
- m is an integer of at least 3; and
wherein said at least one polysiloxane compound having the formula (III) is grafted to said at least one polymer (P) through reaction of at least a fraction of the -CH=CH2 moiety of monomer (M) with the H-Si moiety of the polysiloxane compound having the formula (III) (see from line 6 of claim 16 of 339’, “said polymer electrolyte being obtained by reaction between:”, to the end of claim 16 of 339’; separately see from line 6 of claim 29 of 339’, “said polymer electrolyte being obtained by reaction between:”, to the end of claim 29 of 339’).
Regarding claim 12, 339’ teaches wherein from 80.0 % by moles to 99.0 % by moles of the recurring units of the polymer (P) are EO units (see claim 17 of 339’).
Regarding claim 13, 339’ teaches wherein from 0.5 % by moles to 5.0 % by moles, or from 0.5 % by moles to 4.0 % by moles, or from 1.0 % by moles to 4.0 % by moles, or from 1.0 % by moles to 3.0 % by moles of the recurring units of the polymer (P) are PO units (see claim 18 of 339’).
Regarding claim 14, 339’ teaches wherein from 1.2 % by moles to 4.0 % by moles, or from 1.5 % by moles to 3.5 % by moles, or from 1.5 % by moles to 3.0 % by moles of the recurring units of the polymer (P) are recurring units derived from the monomer (M) of general formula (I) or of general formula (II) wherein R1, R2, n and X are as defined in claim 11 (see claim 19 of 339’).
Regarding claim 15, 339’ teaches wherein the monomer (M) is of formula (II)
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wherein
- each of R1 and R2, equal to or different from each other and at each occurrence, is a C1-2 alkanediyl and n is an integer 0 or 1 (see claim 20 of 339’).
Regarding claim 17, 339’ teaches wherein each of R3, R4, and R7, equal to or different from each other and at each occurrence, is independently C1-6 alkyl; each of R5 and R6, equal to or different from each other and at each occurrence, is independently selected from C1-4 alkyl or phenyl, wherein said C1-4 alkyl is optionally substituted with one or more substituents selected from halide, C1-4 alkyl, or CF3; m is an integer of at least 5 and at most 1000 (see claim 21 of 339’).
Regarding claim 20, 339’ teaches wherein the polysiloxane compound having formula (III) is grafted to polymer (P) through reaction of at least 10% and at most 90% by moles, of the-CH=CH2 moiety of monomer (M) with the H-Si moiety of the polysiloxane compound having the formula (III) (see claim 22 of 339’).
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Claim Rejections - 35 USC § 102
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 (i.e., changing from AIA to pre-AIA ) 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.
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claims 11-15, 17-19 and 21 are rejected under 35 U.S.C. 102 (a)(1) as being anticipated by Masaaki et al. (JP H08165349 A, provided on the IDS filed 6/26/2024 and 8/12/2025, citation see machine translate).
Regarding Claim 11, Masaaki et al. teaches a polymer (polyoxyalkylene having a silicone group in a side chain, [0001]) being obtained by reaction (see [0025]) between:
i. at least one polyether polymer (formula (9), [0019]; when Z = -CH2-CH2-, A1O = -CH2-CH(CH3)-O- (recurring unit of propylene oxide (PO)), a=2, i+p=0, m=1; A2O = -CH2-CH-O- (recurring unit of ethylene oxide (EO)); see “AO represent oxyalkylene groups having 2 to 22 carbon atoms”, [0009]; b=96, (B2O) = (-CH2-CH(-CH2-O-CH2-CH=CH2)-O-, recurring unit of allyl glycidyl ether (AGE)), see [0023]; j+q=2, n=1, the formula (9) is (PO)2-O-CH2-CH2-O-(EO)96-(AGE)2) [hereinafter polymer (P)], said polymer (P) ((PO)2-O-CH2-CH2-O-(EO)96-(AGE)2, see formula (9), [0019]) comprising:
a) at least 70.0 % by moles of oxyethylene units (EO) (96% by moles of EO; see (PO)2-O-CH2-CH2-O-(EO)96-(AGE)2, formula (9), [0019]);
b) from 0.0 to 10.0 % by moles of oxypropylene units (PO) (2% by moles of PO; see (PO)2-O-CH2-CH2-O-(EO)96-(AGE)2, formula (9), [0019]); and
c) from 1.00 to 4.0 % by moles (2% by moles of allyl glycidyl ether (AGE); see (PO)2-O-CH2-CH2-O-(EO)96-(AGE)2, formula (9), [0019], [0023]) of recurring units derived from at least one monomer [hereinafter, monomer (M)] of general formula (I) or of general formula (II) (allyl glycidyl ether (AGE), [0023]):
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wherein
- each of R1 and R2, equal to or different from each other and at each occurrence, is C1-6 alkanediyl wherein said C1-6 alkanediyl, is optionally substituted with one or more substituents selected from halide, C1-4 alkyl, C3-6 cycloalkyl, CF3, and OR8, and wherein each of R8, equal to or different from each other and at each occurrence, is independently selected from the group hydrogen and C1-4 alkyl; n is an integer 0 or 1 or 2 (both R1 and R2 is -CH2- and n = 1; see allyl glycidyl ether (AGE), [0023]);
- each of X is a leaving group selected from the group consisting of halide, trifluoromethanesulfonate, nonafluorobutanesulfonate, p-toluenesulfonate and methanesulfonate;
and
ii. at least one polysiloxane compound having the formula (III) (formula (10), [0019]; when R = methyl and r=14, formula (10) is r = 14 silysine-terminated polydimethylsiloxane, see [0020]; note: r = 14 silysine-terminated polydimethylsiloxane is a one-end terminated mono-hydride polydimethylsiloxane (PDMS))
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wherein
- each of R3, R4, R5, R6 and R7, equal to or different from each other and at each occurrence, is independently selected from the group consisting of C1-6 alkyl, C3-6 cycloalkyl, aryl, C1-6 alkoxy, and heterocyclyl, wherein said C1-6 alkyl, C3-6 cycloalkyl, aryl, C1-6 alkoxy, heterocyclyl are optionally substituted with one or more substituents selected from halide, C1-4 alkyl, C3-6 cycloalkyl, CF3, and OR9, and wherein each of R9, equal to or different from each other and at each occurrence, is independently selected from the group consisting of hydrogen, C1-4 alkyl, and a hydroxyl protecting group (each R3, R4, R5, R6 and R7 is methyl, -CH3-; see r = 14 silysine-terminated polydimethylsiloxane, see [0020]),
- m is an integer of at least 3 (m=14; see r = 14 silysine-terminated polydimethylsiloxane, see [0020]); and
wherein said at least one polysiloxane compound having the formula (III) (formula (10), [0025]) is grafted to said at least one polymer (P) (formula (9), [0025]) through reaction of at least a fraction of the -CH=CH2 (carbon-carbon double bond, [0025]) moiety of monomer (M) with the H-Si moiety (the silysine group, [0025]) of the polysiloxane compound having the formula (III).
Claim 11 further includes a preamble requiring that the composition is a polymer electrolyte; however, Masaaki is silent as to the composition being a polymer electrolyte. Since the body of the claim sets forth the required structure, and Masaaki teaches all of the limitations contained therein, the composition of Masaaki is found to be a polymer electrolyte, or otherwise the claim is found to omit essential elements which provide the polymer electrolyte function to the claimed composition.
Regarding claim 12, Masaaki et al. teaches wherein from 80.0 % by moles to 99.0 % by moles of the recurring units of the polymer (P) are EO units (96% by moles of EO; see (PO)2-O-CH2-CH2-O-(EO)96-(AGE)2, see formula (9), [0019]).
Regarding claim 13, Masaaki et al. teaches wherein from 0.5 % by moles to 5.0 % by moles, or from 0.5 % by moles to 4.0 % by moles, or from 1.0 % by moles to 4.0 % by moles, or from 1.0 % by moles to 3.0 % by moles of the recurring units of the polymer (P) are PO units. (2% by moles of PO; see (PO)2-O-CH2-CH2-O-(EO)96-(AGE)2, see formula (9), [0019])
Regarding claim 14, Masaaki et al. teaches wherein from 1.2 % by moles to 4.0 % by moles, or from 1.5 % by moles to 3.5 % by moles, or from 1.5 % by moles to 3.0 % by moles of the recurring units of the polymer (P) are recurring units derived from the monomer (M) of general formula (I) or of general formula (II) wherein R1, R2, n and X are as defined in claim 11 (2% by moles of allyl glycidyl ether (AGE); see (PO)2-O-CH2-CH2-O-(EO)96-(AGE)2, see formula (9), [0019], [0023]).
Regarding claim 15, Masaaki et al. teaches wherein the monomer (M) is of formula (II) (see allyl glycidyl ether, see [0023])
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wherein
- each of R1 and R2, equal to or different from each other and at each occurrence, is a C1-2 alkanediyl and n is an integer 0 or 1 (both R1 and R2 is -CH2- and n = 1; see allyl glycidyl ether, [0023]).
Regarding claim 17, Masaaki et al. teaches wherein each of R3, R4, and R7, equal to or different from each other and at each occurrence, is independently C1-6 alkyl; each of R5 and R6, equal to or different from each other and at each occurrence, is independently selected from C1-4 alkyl or phenyl, wherein said C1-4 alkyl is optionally substituted with one or more substituents selected from halide, C1-4 alkyl, or CF3 (each R3, R4, R5, R6 and R7 is methyl, -CH3-; see r = 14 silysine-terminated polydimethylsiloxane, see [0020]);
m is an integer of at least 5 and at most 1000 (m=14; see r = 14 silysine-terminated polydimethylsiloxane, see [0020]).
Regarding claim 18, Masaaki et al. teaches wherein the polymer (P) and the polysiloxane having formula (III) are at least partially dissolved in an organic solvent selected from the group consisting of benzene, toluene, xylene, and cymene (aromatic solvents such as toluene and xylene, see [0027]).
Regarding claim 19, Masaaki et al. teaches wherein the polysiloxane compound having the formula (III) is grafted to the polymer (P) in the presence of a catalyst (catalyst, see [0025]).
Regarding claim 21, Masaaki et al. teaches wherein the catalyst is a hydrosilylation catalyst selected from the group consisting of a Karstedt's catalyst (platinum-olefin complex, see [0025]), a Wilkinson catalyst, a Speier catalyst (chloroplatinic acid, see [0025]), and mixtures thereof.
Claim Rejections - 35 USC § 103
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 (i.e., changing from AIA to pre-AIA ) 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.
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.
Claim 16 is rejected under 35 U.S.C. 103 as being unpatentable over Masaaki et al. (JP H08165349 A, provided on the IDS filed 6/26/2024 and 8/12/2025, citation see machine translate).
Regarding Claim 16, Masaaki et al. teaches wherein the polymer (P) is a random copolymer (random manner, see [0019]),
In another embodiment, Masaaki et al. teaches having an Mn (number average molecular weight) of at least 10 000 g/mol and at most 150 000 g/mol (27,565 g/mol, see example 7, [0043], Table 4, fourth column from the left; example 7 structure see Table 6, [0048]; note: calculation Mn of see below).
Calculation of Mn of example 7: Mn of example 7 = Mn of polysiloxane grafted polymer – 4 X 5 X Mn of polysiloxane (see Examiner Annotated Table 6) = 44,300 g/mol (example 7, [0043], Table 4, fourth column from the left) – 4 X 5 X (Mn of Si15C31O14H91) = 44,300 g/mol – (4 X 5 X 836.75 g/mol) = 27,565 g/mol.
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Claim 20 is rejected under 35 U.S.C. 103 as being unpatentable over Masaaki et al. (JP H08165349 A, provided on the IDS filed 6/26/2024 and 8/12/2025, citation see machine translate) in view of Blevins et al. (Patent No. 4,962,218, provided in the IDS filed 6/19/2023).
Regarding Claim 20, Masaaki et al. teaches wherein the polysiloxane compound having formula (III) (formula (10), [0025]) is grafted to polymer (P) (formula (9), [0025]) through reaction of the-CH=CH2 (carbon-carbon double bond, [0025]) moiety of monomer (M) with the H-Si moiety (the silysine group, [0025]) of the polysiloxane compound having the formula (III).
Masaaki et al. is silent on the conversion of the-CH=CH2 moiety of monomer (M) is at least 10% and at most 90%.
Blevins et al. teaches the same type of reaction (hydrosilation, col. 8, line 1) wherein the polysiloxane compound (monofunctional siloxane, col. 7, lines 43-45) having formula (III) (one example: MD3M’ ((CH3)3SiO[Si(CH3)2O]3Si(CH3)2H), col. 8, lines 42-44) is grafted to polymer (P) (multifunctional polyether by alkoxylation of EO and/or PO with allyl glycidyl ether (AGE), col. 7, lines 50-51) that at least 10% and at most 90% (less than 90%, col. 8, line 2) by moles, of the-CH=CH2 moiety (allyl (or vinyl), col. 7, line 61) of monomer (M) with the H-Si moiety (SiH, col. 7, line 61) of the polysiloxane compound having the formula (III).
It would have been obvious to one of ordinary skill in the art before the effective filing date of the invention to run the reaction taught by Masaaki et al. such that at least 10% and less than 90% of the-CH=CH2 moiety of monomer (M) reacts with the H-Si moiety as taught by Blevins et al. because remaining unsaturation was present as propenyl functionalities, which suggests that allyl-to-propenyl isomerization competes with hydrosilation (see Blevins et al. col. 8, lines 4-8).
Claims 11-15, 17-19 and 21 are rejected under 35 U.S.C. 103 as being unpatentable over Masaaki et al. (JP H08165349 A, provided on the IDS filed 6/26/2024 and 8/12/2025, citation see machine translate) in view of Miura et al. (Patent No. 6,878,491).
Regarding Claim 11, Masaaki et al. teaches a polymer (polyoxyalkylene having a silicone group in a side chain, [0001]) being obtained by reaction (see [0025]) between:
i. at least one polyether polymer (formula (9), [0019]; when Z = -CH2-CH2-, A1O = -CH2-CH(CH3)-O- (recurring unit of propylene oxide (PO)), a=2, i+p=0, m=1; A2O = -CH2-CH-O- (recurring unit of ethylene oxide (EO)); see “AO represent oxyalkylene groups having 2 to 22 carbon atoms”, [0009]; b=96, (B2O) = (-CH2-CH(-CH2-O-CH2-CH=CH2)-O-, recurring unit of allyl glycidyl ether (AGE)), see [0023]; j+q=2, n=1, the formula (9) is (PO)2-O-CH2-CH2-O-(EO)96-(AGE)2) [hereinafter polymer (P)], said polymer (P) ((PO)2-O-CH2-CH2-O-(EO)96-(AGE)2, see formula (9), [0019]) comprising:
a) at least 70.0 % by moles of oxyethylene units (EO) (96% by moles of EO; see (PO)2-O-CH2-CH2-O-(EO)96-(AGE)2, formula (9), [0019]);
b) from 0.0 to 10.0 % by moles of oxypropylene units (PO) (2% by moles of PO; see (PO)2-O-CH2-CH2-O-(EO)96-(AGE)2, formula (9), [0019]); and
c) from 1.00 to 4.0 % by moles (2% by moles of allyl glycidyl ether (AGE); see (PO)2-O-CH2-CH2-O-(EO)96-(AGE)2, formula (9), [0019], [0023]) of recurring units derived from at least one monomer [hereinafter, monomer (M)] of general formula (I) or of general formula (II) (allyl glycidyl ether (AGE), [0023]):
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wherein
- each of R1 and R2, equal to or different from each other and at each occurrence, is C1-6 alkanediyl wherein said C1-6 alkanediyl, is optionally substituted with one or more substituents selected from halide, C1-4 alkyl, C3-6 cycloalkyl, CF3, and OR8, and wherein each of R8, equal to or different from each other and at each occurrence, is independently selected from the group hydrogen and C1-4 alkyl; n is an integer 0 or 1 or 2 (both R1 and R2 is -CH2- and n = 1; see allyl glycidyl ether (AGE), [0023]);
- each of X is a leaving group selected from the group consisting of halide, trifluoromethanesulfonate, nonafluorobutanesulfonate, p-toluenesulfonate and methanesulfonate;
and
ii. at least one polysiloxane compound having the formula (III) (formula (10), [0019]; when R = methyl and r=14, formula (10) is r = 14 silysine-terminated polydimethylsiloxane, see [0020]; note: r = 14 silysine-terminated polydimethylsiloxane is a one-end terminated mono-hydride polydimethylsiloxane (PDMS))
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wherein
- each of R3, R4, R5, R6 and R7, equal to or different from each other and at each occurrence, is independently selected from the group consisting of C1-6 alkyl, C3-6 cycloalkyl, aryl, C1-6 alkoxy, and heterocyclyl, wherein said C1-6 alkyl, C3-6 cycloalkyl, aryl, C1-6 alkoxy, heterocyclyl are optionally substituted with one or more substituents selected from halide, C1-4 alkyl, C3-6 cycloalkyl, CF3, and OR9, and wherein each of R9, equal to or different from each other and at each occurrence, is independently selected from the group consisting of hydrogen, C1-4 alkyl, and a hydroxyl protecting group (each R3, R4, R5, R6 and R7 is methyl, -CH3-; see r = 14 silysine-terminated polydimethylsiloxane, see [0020]),
- m is an integer of at least 3 (m=14; see r = 14 silysine-terminated polydimethylsiloxane, see [0020]); and
wherein said at least one polysiloxane compound having the formula (III) (formula (10), [0025]) is grafted to said at least one polymer (P) (formula (9), [0025]) through reaction of at least a fraction of the -CH=CH2 (carbon-carbon double bond, [0025]) moiety of monomer (M) with the H-Si moiety (the silysine group, [0025]) of the polysiloxane compound having the formula (III).
Masaaki et al. is silent the polymer is a polymer electrolyte suitable for use in lithium-ion secondary batteries.
Miura et al. teaches a polymer electrolyte obtained by using the same type of polymer: a multi-component copolymer in which propylene oxide and ethylene oxide are combined with a further crosslinkable oxirane compound (see col. 1, lines 50-58).
It would have been obvious to one of ordinary skill in the art before the effective filling date of the claimed invention to configure the polymer taught by Masaaki et al. to be a polymer electrolyte as taught by Miura et al. because a solid electrolyte having an excellent ionic conductivity and showing little plastic deformation or fluidity even at a high temperature can be obtained by using a multi-component copolymer in which propylene oxide and ethylene oxide are combined with a further crosslinkable oxirane compound (see Miura et al. col. 1, lines 50-58). It is noted that the body of claim 1 as worded does not contain any specific structure beyond that taught by Masaaki et al. which causes the composition to function as a polymer electrolyte.
Regarding claim 12, Masaaki et al. in view of Miura et al. teaches wherein from 80.0 % by moles to 99.0 % by moles of the recurring units of the polymer (P) are EO units (96% by moles of EO; see (PO)2-O-CH2-CH2-O-(EO)96-(AGE)2, Masaaki et al. formula (9), [0019]).
Regarding claim 13, Masaaki et al. in view of Miura et al. teaches wherein from 0.5 % by moles to 5.0 % by moles, or from 0.5 % by moles to 4.0 % by moles, or from 1.0 % by moles to 4.0 % by moles, or from 1.0 % by moles to 3.0 % by moles of the recurring units of the polymer (P) are PO units. (2% by moles of PO; see (PO)2-O-CH2-CH2-O-(EO)96-(AGE)2, Masaaki et al. formula (9), [0019])
Regarding claim 14, Masaaki et al. in view of Miura et al. teaches wherein from 1.2 % by moles to 4.0 % by moles, or from 1.5 % by moles to 3.5 % by moles, or from 1.5 % by moles to 3.0 % by moles of the recurring units of the polymer (P) are recurring units derived from the monomer (M) of general formula (I) or of general formula (II) wherein R1, R2, n and X are as defined in claim 11 (2% by moles of allyl glycidyl ether (AGE); see (PO)2-O-CH2-CH2-O-(EO)96-(AGE)2, Masaaki et al. formula (9), [0019], [0023]).
Regarding claim 15, Masaaki et al. in view of Miura et al. teaches wherein the monomer (M) is of formula (II) (see allyl glycidyl ether, Masaaki et al. [0023])
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wherein
- each of R1 and R2, equal to or different from each other and at each occurrence, is a C1-2 alkanediyl and n is an integer 0 or 1 (both R1 and R2 is -CH2- and n = 1; see allyl glycidyl ether, Masaaki et al. [0023]).
Regarding claim 17, Masaaki et al. in view of Miura et al. teaches wherein each of R3, R4, and R7, equal to or different from each other and at each occurrence, is independently C1-6 alkyl; each of R5 and R6, equal to or different from each other and at each occurrence, is independently selected from C1-4 alkyl or phenyl, wherein said C1-4 alkyl is optionally substituted with one or more substituents selected from halide, C1-4 alkyl, or CF3 (each R3, R4, R5, R6 and R7 is methyl, -CH3-; see r = 14 silysine-terminated polydimethylsiloxane, Masaaki et al. [0020]);
m is an integer of at least 5 and at most 1000 (m=14; see r = 14 silysine-terminated polydimethylsiloxane, Masaaki et al. [0020]).
Regarding claim 18, Masaaki et al. in view of Miura et al. teaches wherein the polymer (P) and the polysiloxane having formula (III) are at least partially dissolved in an organic solvent selected from the group consisting of benzene, toluene, xylene, and cymene (aromatic solvents such as toluene and xylene, see Masaaki et al. [0027]).
Regarding claim 19, Masaaki et al. in view of Miura et al. teaches wherein the polysiloxane compound having the formula (III) is grafted to the polymer (P) in the presence of a catalyst (catalyst, see Masaaki et al. [0025]).
Regarding claim 21, Masaaki et al. in view of Miura et al. teaches wherein the catalyst is a hydrosilylation catalyst selected from the group consisting of a Karstedt's catalyst (platinum-olefin complex, see Masaaki et al. [0025]), a Wilkinson catalyst, a Speier catalyst (chloroplatinic acid, see Masaaki et al. [0025]), and mixtures thereof.
Claim 16 is rejected under 35 U.S.C. 103 as being unpatentable over Masaaki et al. (JP H08165349 A, provided on the IDS filed 6/26/2024 and 8/12/2025, citation see machine translate) in view of Miura et al. (Patent No. 6,878,491).
Regarding Claim 16, Masaaki et al. in view of Miura et al. teaches wherein the polymer (P) is a random copolymer (random manner, see Masaaki et al. [0019]), having an Mn (number average molecular weight) of at least 10 000 g/mol and at most 150 000 g/mol (27,565 g/mol, see Masaaki et al. example 7, [0043], Table 4, fourth column from the left; Masaaki et al. example 7 structure see Table 6, [0048]; note: calculation Mn of see below).
Calculation of Mn of example 7: Mn of example 7 = Mn of polysiloxane grafted polymer – 4 X 5 X Mn of polysiloxane (see Examiner Annotated Table 6) = 44,300 g/mol (Masaaki et al. example 7, [0043], Table 4, fourth column from the left) – 4 X 5 X (Mn of Si15C31O14H91) = 44,300 g/mol – (4 X 5 X 836.75 g/mol) = 27,565 g/mol.
Claim 20 is rejected under 35 U.S.C. 103 as being unpatentable over Masaaki et al. (JP H08165349 A, provided on the IDS filed 6/26/2024 and 8/12/2025, citation see machine translate) in view of Miura et al. (Patent No. 6,878,491) in view of Blevins et al. (Patent No. 4,962,218, provided in the IDS filed 6/19/2023).
Regarding Claim 20, Masaaki et al. in view of Miura et al. teaches wherein the polysiloxane compound having formula (III) (formula (10), [0025]) is grafted to polymer (P) (formula (9), [0025]) through reaction of the-CH=CH2 (carbon-carbon double bond, [0025]) moiety of monomer (M) with the H-Si moiety (the silysine group, [0025]) of the polysiloxane compound having the formula (III).
Masaaki et al. in view of Miura et al. is silent on the conversion the-CH=CH2 moiety of monomer (M) is at least 10% and at most 90%.
Blevins et al. teaches the same type of reaction (hydrosilation, col. 8, line 1) wherein the polysiloxane compound (monofunctional siloxane, col. 7, lines 43-45) having formula (III) (one example: MD3M’ ((CH3)3SiO[Si(CH3)2O]3Si(CH3)2H), col. 8, lines 42-44) is grafted to polymer (P) (multifunctional polyether by alkoxylation of EO and/or PO with allyl glycidyl ether (AGE), col. 7, lines 50-51) that at least 10% and at most 90% (less than 90%, col. 8, line 2) by moles, of the-CH=CH2 moiety (allyl (or vinyl), col. 7, line 61) of monomer (M) with the H-Si moiety (SiH, col. 7, line 61) of the polysiloxane compound having the formula (III).
It would have been obvious to one of ordinary skill in the art before the effective filing date of the invention to run the reaction taught by Masaaki et al. in view of Miura et al. such that at least 10% and less than 90% of the-CH=CH2 moiety of monomer (M) reacts with the H-Si moiety as taught by Blevins et al. because remaining unsaturation was present as propenyl functionalities, which suggests that allyl-to-propenyl isomerization competes with hydrosilation (see Blevins et al. col. 8, lines 4-8).
Conclusion
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/NING CHEN/Examiner, Art Unit 1723 /TIFFANY LEGETTE/Supervisory Patent Examiner, Art Unit 1723