DETAILED ACTION
Application 18/547,812, “DIELECTRIC THERMAL MANAGEMENT FLUIDS AND METHODS FOR USING THEM”, was filed with the USPTO on 8/24/2023 and has a PRO 63/153,148 filed on 2/24/2021.
This office action is in response to communication filed on 6/15/2026.
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 .
Election/Restrictions
Applicant’s election without traverse of Group II, drawn to a method in the reply filed on 6/15/2026 is acknowledged. Claims 1-20 are canceled and claims 21-40 are newly added and pending. Note: there is a typo in applicant remarks filed on 6/15/2026 that “new method claims 21-39 are added” appears to be “claims 21-40”.
Information Disclosure Statement
The information disclosure statement (IDS) submitted on 8/24/2023 and 6/15/2026 are in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statement is being considered by the examiner.
Drawings
The drawings are objected to as failing to comply with 37 CFR 1.84(p)(5) because they do not include the following reference sign(s) mentioned in the description: 300 and 360 (PGpub [0101]); 152 (PGpub [0098]). Corrected drawing sheets in compliance with 37 CFR 1.121(d) are required in reply to the Office action to avoid abandonment of the application. Any amended replacement drawing sheet should include all of the figures appearing on the immediate prior version of the sheet, even if only one figure is being amended. Each drawing sheet submitted after the filing date of an application must be labeled in the top margin as either “Replacement Sheet” or “New Sheet” pursuant to 37 CFR 1.121(d). If the changes are not accepted by the examiner, the applicant will be notified and informed of any required corrective action in the next Office action. The objection to the drawings will not be held in abeyance.
Specification
The disclosure is objected to because of the following informalities:
“ASTM D2270” in Table 2 (PGpub [0116]) is measuring viscosity index, its value does not match unit cSt;
“ASTM D455” in PGpub [0035], [0074], [0170]-[0173] and [0186]-[0188] appears to be a typo and “ASTM D455” appears to be “ASTM D445”;
PGpub [0083]: “25 C” and “30 C” missing degree symbols;
“cooper corrosiveness” in Table 2 should read “copper corrosiveness”;
PGpub [0115]: 2-ethylhexylbromide (168 g, 0.87 mmol, 1.0 equivalents), “mmol” should read “mol”;
PGpub [0115]: The mixture was stirrer at 120° C, “stirrer” should read “stirred”;
Both PGpub [0218] and [0219] (also see [0162] and [0163] spec filed 8/24/2023) are labeled “Embodiment 73”;
PGpub [0231]: “Embodiment 76 is directed to the method of embodiment 73”, but embodiment 73 is not a method.
Appropriate correction is required.
Claim Objections
Claims 25 and 26 are objected to because each claim has redundant recitation that already included in claim 21. The recitation is from “wherein the thermal management fluid comprises: one or more dielectric compounds of formula (I)” ……… to “the thermal management fluid has a dielectric constant of at least 1.5 at 25 °C.” The Examiner suggests removing the aforementioned recitation. For examination purposes, the redundant recitation has been removed in claims 25 and 26. Appropriate correction is required.
Claim 33 is objected to because each structure of the last three structures on the list does not match that of claim 21 because the last three structures in claim 33 represent when n =2 but the R5-R6 appear to be different on the two carbons (one carbon has a hydrogen and a methyl group while the other carbon has two hydrogens). The Examiner suggests removing the aforementioned structures. For examination purposes, the last three structures have been removed in claim 33. Appropriate correction is required.
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 21-40 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 21 is indefinite because of the recitation “a thermal management fluid of claim 1”. Claim 1 is canceled therefore it is unclear which thermal management fluid refers to. To overcome the rejection, the Examiner suggests removing “of claim 1” in the aforementioned recitation. For examination purposes, the aforementioned recitation in claim 21 has been interpreted as “a thermal management fluid”.
Claim 26 is indefinite because of the recitation “a thermal management fluid of claim 1”. Claim 1 is canceled therefore it is unclear which thermal management fluid refers to. To overcome the rejection, the Examiner suggests changing the aforementioned recitation to “the thermal management fluid”. For examination purposes, the aforementioned recitation has been interpreted as “the thermal management fluid”.
Claim 26 is indefinite because of the recitation “a heat source” in line 3. It is unclear if it’s the same heat source as in claim 21 or a different heat source. To overcome the rejection, the Examiner suggests changing it to “the heat source”. For examination purposes, the aforementioned recitation has been interpreted as “the heat source”.
Claim 26 recites the limitation “the heat exchanger”, “the pump” and “the connecting duct” in line 6. There is insufficient antecedent basis for this limitation in the claim. To overcome the rejection, the Examiner suggests changing “the” to “a”. For examination purposes, the aforementioned limitations have been interpreted as “a heat exchanger”, “a pump” and “a connecting duct”.
Claim 29 in indefinite because of the limitation “R2 and/or R2”. For examination purposes, claim 29 has been interpreted as “The method of claim 21, wherein branching of R2 is at a β-position to the oxygen atom to which R2 is bound”.
Regarding claims 30, 32, and 37- 40, the phrase "such as" renders the claim indefinite because it is unclear whether the limitations following the phrase are part of the claimed invention. See MPEP § 2173.05(d). To overcome the rejection, the Examiner suggests removing “such as methyl or ethyl” in claim 30; removing “such as C3-C7 alkyl or C3-C6 alkyl” in claims 32 and 37-40. For examination purposes, claim 30 has been interpreted without the limitation “such as methyl or ethyl” and claims 32 and 37-40 have been interpreted without the limitation “such as C3-C7 alkyl or C3-C6 alkyl”.
Regarding claim 30, the phrase "i.e." renders the claim indefinite because it is unclear whether the limitation(s) following the phrase are part of the claimed invention. To overcome the rejection, the Examiner suggests removing “i.e., the compounds have the formula
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” and “i.e., the compounds have the formula
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”. For examination purposes, claim 30 has been interpreted as "The method of claim 21, wherein each of R3, R4, R5, and R6 is H, or wherein each of R4, R5, and R6 is H, and wherein R3 is C1-C6 alkyl”.
Claim 40 is indefinite because the formula of claim 40 does not match that of claim 21. The formula of claim 40 indicates n = 2 but R5 and R6 are different on different carbons, one carbon has one hydrogen and one methyl group while the other has two hydrogens. Therefore, it is unclear which structure the Applicant is claiming in claim 40. For examination purposes, claim 40 has been interpreted as “The method of claim 21, wherein the thermal management fluid further comprises a compound have a structure of formula (II):
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(II); wherein
each of Ra and Rb is independently methyl or ethyl, and each of Rc and Rd is independently C3-C8 alkyl.”.
Claims 22-40 are rejected as they depend from, and therefore incorporate the claimed subject matter from claims rejected under this statute.
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 21-23, 25-28, 30, 34 and 36 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1, 6-8, 10-12 and 14-17 of copending Application No. 18/547,828 (hereinafter 828’) in view of Shiraishi et al. (US 20060171613 A1, provided on IDS filed on 8/24/2023).
Regarding Claim 21, 828’ teaches a method comprising:
contacting a thermal management fluid of claim 1 with a surface having a temperature of at least 25 °C, the surface being in substantial thermal communication with a heat source; and absorbing thermal energy in the thermal management fluid from the heat source through the surface (claim 12 of 828’).
wherein the thermal management fluid comprises:
one or more dielectric compounds of formula (I):
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(claim 1 of 828’) wherein
m is an integer 1, 2, or 3 (when m = 1, 2, or 3, see “m is an integer 1, 2, 3, 4 or 5” in claim 1 of 828’);
n is an integer 1, 2, 3, 4, 5, 6, 7, or 8 (n is an integer 1, 2, 3, 4 or 5, see claim 1 of 828’);
R2 is C6-C12 alkyl;
each R3 and R4 are independently selected from H and C1-C6 alkyl; and
each R5 and R6 are independently selected from H and C1-C6 alkyl;
the one or more dielectric compounds being present in a total amount in the range of 1 wt % to 100 wt %, based on the total weight of the thermal management fluid; and
wherein the thermal management fluid has a flash point of at least 100 °C, measured in accordance with ASTM D93, and the thermal management fluid has a dielectric constant of at least 1.5 at 25° C (claim 1 of 828’).
828’ does not teach R1 is C6-C12 alkyl.
Shiraishi et al. teaches R1 is C6-C12 alkyl (R1 =
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, a C10 alkyl, see
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, the 9th example of generic formula (2) from the top, see [0051]).
It would have been obvious to one of ordinary skill in the art before the effective filling date of the claimed invention to substitute the R1 taught by 828’ with
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, the C10 alkyl taught by Shiraishi et al. to have a good balance between heat resistance and low temperature fluidity when having C8 to C12 alkyl groups (see Shiraishi et al. [0048]).
Regarding claim 22, 828’ in view of Shiraishi et al. teaches wherein the surface has a temperature in the range of 50 °C to 150 °C (claim 17 of 828’).
Regarding claim 23, 828’ in view of Shiraishi et al. teaches wherein the heat source is a battery system, a capacitor, inverter, electrical cabling, a fuel cell, a motor, a computer, or high power charging equipment (claim 16 of 828’).
Regarding claim 25, 828’ in view of Shiraishi et al. teaches wherein the thermal management fluid is disposed in a fluid path (claim 14 of 828’) of a battery system (battery system, claim 14 of 828’) comprising:
a housing; and
one or more electrochemical cells disposed in the housing,
the fluid path extending in the housing and in substantial thermal communication with the one or more electrochemical cells (claim 14 of 828’) (interpretation see claim objection above).
828’ in view of Shiraishi et al. does not teach the thermal management fluid is configured to circulate in a fluid path.
Claim 15 of 828’ teaches the thermal management fluid is configured to circulate in a fluid path (see claim 15 of 828’).
It would have been obvious to one of ordinary skill in the art before the effective filling date of the claimed invention to modify the thermal management fluid taught by 828’ in view of Shiraishi et al. to be configured to circulate in the fluid path as taught by claim 15 of 828’ to absorb thermal energy produced by the heat source (see claim 15 of 828’).
Regarding claim 26, 828’ in view of Shiraishi et al. teaches wherein the thermal management fluid is disposed in and configured to circulate in a fluid path (see claim 15 of 828’) of a thermal management circuit (a thermal management circuit, see claim 15 of 828’) comprising:
the fluid path extending around and/or through a heat source;
a thermal management fluid of claim 1, disposed in and configured to circulate in the fluid path and to absorb thermal energy produced by the heat source,
wherein the fluid is disposed in the fluid path, the heat exchanger, the pump and the connecting duct (claim 15 of 828’) (interpretation see claim objection and 112b rejection above).
Regarding claim 27, 828’ in view of Shiraishi et al. teaches wherein each of the one or more compounds contains a total number of carbon atoms from 14 to 50 (15 to 39; note: 10 to 30, see claim 8 of 828’; plus the additional carbon atoms when the C1-C5 R1 of 828’ substituted with C10 of Shiraishi, so additional 5-9 carbon atoms, therefore 10 + 5 to 30 + 9).
Regarding claim 28, 828’ in view of Shiraishi et al. teaches wherein R1 is C6-C10 alkyl (R1 =
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, a C10 alkyl, see
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, the 9th example of generic formula (2) from the top, see Shiraishi et al. [0051]) and R2 is C6-C10 alkyl (R2 is C6-C10 alkyl, see claim 6 of 828’).
Regarding claim 30, 828’ in view of Shiraishi et al. teaches wherein each of R3, R4, R5, and R6 is H (see the structure of claim 6 of 828’), i.e., the compounds have the formula
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(interpretation see 112b rejection above); or
wherein each of R4, R5, and R6 is H, and wherein R3 is C1-C6 alkyl (such as methyl or ethyl), i.e., the compounds have the formula
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.
Regarding claim 34, wherein the one or more dielectric compounds is present in an amount in the range of 50 wt% to 99.9 wt% (50 wt% to 100 wt%, see claim 10 of 828’).
Regarding claim 36, wherein the thermal management fluid has a kinematic viscosity at 40 °C in the range of 1.5 to 20 cSt, all as measured in accordance with ASTM D455 (claim 11 of 828’).
This is a provisional nonstatutory double patenting rejection.
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.
Claims 21-31, 34-37 and 39-40 are rejected under 35 U.S.C. 103 as being unpatentable over Prentice et al. (WO 2020007954 A1, citations see machine translation filed on 4/15/2026) in view of Shiraishi et al. (US 20060171613 A1, provided on IDS filed on 8/24/2023).
Regarding Claim 21, Prentice et al. teaches a method (Embodiment 34 [0111]; note: Embodiment 34 based on embodiment 30 [0107], embodiment 30 see embodiment 28 [0105] based on embodiment 4 [0081] based on embodiment 1 [0078]) comprising:
contacting a thermal management fluid of claim 1 (aliphatic dielectric fluid oxygenates (ethers), [0081]; interpretation see 112b rejection above) with a surface having a temperature of at least 25 °C, the surface being in substantial thermal communication with a heat source; and absorbing thermal energy in the thermal management fluid from the heat source through the surface (see [0107]).
the one or more dielectric compounds being present in a total amount in the range of 1 wt % to 100 wt % (65 wt% to 99.9 wt%, [0078]), based on the total weight of the thermal management fluid; and
wherein the thermal management fluid has a flash point of at least 100 °C (flash point of at least 100 °C, [0105]), measured in accordance with ASTM D93, and the thermal management fluid has a dielectric constant of at least 1.5 at 25° C (dielectric constant of at least 1.5 at 25 °C, [0078]).
Prentice et al. does not teach wherein the thermal management fluid comprises:
one or more dielectric compounds of formula (I):
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wherein
m is an integer 1, 2, or 3; n is an integer 1, 2, 3, 4, 5, 6, 7, or 8;
R1 is C6-C12 alkyl; R2 is C6-C12 alkyl;
each R3 and R4 are independently selected from H and C1-C6 alkyl; and
each R5 and R6 are independently selected from H and C1-C6 alkyl.
Shiraishi et al. teaches wherein the thermal management fluid (aliphatic tetraether, [0059]) comprises:
one or more dielectric compounds (
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, see first concrete example of generic formula (4), [0059])
of formula (I):
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(
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, see first concrete example of generic formula (4), [0059])
wherein
m is an integer 1, 2, or 3 (m = 3, see
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, [0059]);
n is an integer 1, 2, 3, 4, 5, 6, 7, or 8 (n = 3, see
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, [0059]);
R1 is C6-C12 alkyl (C7 alkyl; see R1 =
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);
R2 is C6-C12 alkyl (C7 alkyl; see R2 =
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);
each R3 and R4 are independently selected from H and C1-C6 alkyl; and
each R5 and R6 are independently selected from H and C1-C6 alkyl (R3, R4, R5, and R6 is H, see
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, [0059]).
It would have been obvious to one of ordinary skill in the art before the effective filling date of the claimed invention to modify the ethers taught by Prentice et al. by adding the aliphatic tetraether with the formula of
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taught by Shiraishi et al. to acquire the same effect as mono- or diether compounds and to improve the trade-off between a viscosity index and a solidification temperature (see Shiraishi et al. [0054]).
Regarding claim 22, Prentice et al. in view of Shiraishi et al. is silent wherein the surface has a temperature in the range of 50 °C to 150 °C.
A different embodiment of Prentice et al. teaches wherein the surface has a temperature in the range of 50 °C to 150 °C (50 °C to 150 °C, [0060]).
It would have been obvious to one of ordinary skill in the art before the effective filling date of the claimed invention to modify the surface temperature taught by Prentice et al. in view of Shiraishi et al. to be in the range of 50 °C to 150 °C taught by Prentice et al. because the temperature of the surface can vary (see Prentice et al. [0060]). Further, it has been held that combining two embodiments disclosed adjacent to each other in a prior art patent does not require a leap of inventiveness and involves only routine skill in the art.
Regarding claim 23, Prentice et al. in view of Shiraishi et al. teaches wherein the heat source is a battery system, a capacitor, inverter, electrical cabling, a fuel cell, a motor, a computer (see Prentice [0111]), or high power charging equipment.
Regarding claim 24, Prentice et al. in view of Shiraishi et al. teaches wherein the heat source is one or more electrochemical cells (battery system, Prentice [0111]; note: by definition, a battery system has one or more electrochemical cells.).
Regarding claim 25, Prentice et al. in view of Shiraishi et al. does not teach wherein the thermal management fluid is disposed in and configured to circulate in a fluid path of a battery system comprising:
a housing; and
one or more electrochemical cells disposed in the housing,
the fluid path extending in the housing and in substantial thermal communication with the one or more electrochemical cells.
Another embodiment of Prentice et al. (Embodiment 38, [0115]) teaches wherein the thermal management fluid is disposed in in a fluid path of a battery system comprising:
a housing; and
one or more electrochemical cells disposed in the housing,
the fluid path extending in the housing and in substantial thermal communication with the one or more electrochemical cells (see [0115]) (interpretation see claim objection above).
It would have been obvious to one of ordinary skill in the art before the effective filling date of the claimed invention to dispose the ethers comprising the aliphatic tetraethers taught by Prentice et al. in view of Shiraishi et al. in the battery pack taught by Prentice et al. to absorb the large amount of heat quickly as it is produced during fast charging because of the high heat capacity of the thermal management fluid (see Prentice et al. [0067]). Further, it has been held that combining two embodiments disclosed adjacent to each other in a prior art patent does not require a leap of inventiveness and involves only routine skill in the art.
However, Prentice et al. in view of Shiraishi et al. does not teach the thermal management fluid is configured to circulate in a fluid path.
A different embodiment of Prentice et al. (Embodiment 43, [0120]) teaches the thermal management fluid is configured to circulate in a fluid path (see [0120]).
It would have been obvious to one of ordinary skill in the art before the effective filling date of the claimed invention to modify the ethers comprising the aliphatic tetraethers taught by Prentice et al. in view of Shiraishi et al. to be configured to circulate in the fluid path as taught by Prentice et al. to absorb thermal energy produced by the heat source (see Prentice et al. [0120]). Further, it has been held that combining two embodiments disclosed adjacent to each other in a prior art patent does not require a leap of inventiveness and involves only routine skill in the art.
Regarding claim 26, Prentice et al. in view of Shiraishi et al. does not teach wherein the thermal management fluid is disposed in and configured to circulate in a fluid path of a thermal management circuit comprising:
the fluid path extending around and/or through a heat source;
a thermal management fluid of claim 1, disposed in and configured to circulate in the fluid path and to absorb thermal energy produced by the heat source,
wherein the fluid is disposed in the fluid path, the heat exchanger, the pump and the connecting duct.
Another embodiment of Prentice et al. (Embodiment 43, [0120]) teaches wherein the thermal management fluid is disposed in and configured to circulate in a fluid path of a thermal management circuit comprising:
the fluid path extending around and/or through a heat source;
a thermal management fluid of claim 1, disposed in and configured to circulate in the fluid path and to absorb thermal energy produced by the heat source,
wherein the fluid is disposed in the fluid path, the heat exchanger, the pump and the connecting duct (see [0120]) (interpretation see claim objection).
It would have been obvious to one of ordinary skill in the art before the effective filling date of the claimed invention to dispose and circulate the ethers comprising the aliphatic tetraethers taught by Prentice et al. in view of Shiraishi et al. in the thermal management circuit taught by Prentice et al. to absorb thermal energy produced by the heat source (see Prentice et al. [0120]). Further, it has been held that combining two embodiments disclosed adjacent to each other in a prior art patent does not require a leap of inventiveness and involves only routine skill in the art.
Regarding claim 27, Prentice et al. in view of Shiraishi et al. teaches wherein each of the one or more compounds (
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, see first concrete example of generic formula (4), Shiraishi [0059]) contains a total number of carbon atoms from 14 to 50 (26, by counting total number of carbon atoms in
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, Shiraishi [0059]).
Regarding claim 28, Prentice et al. in view of Shiraishi et al. teaches wherein R1 is C6-C10 alkyl (C7 alkyl; see Shiraishi R1 =
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)and R2 is C6-C10 alkyl (C7 alkyl; see Shiraishi R2 =
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).
Regarding claim 29, Prentice et al. in view of Shiraishi et al. teaches wherein branching of R2 (-CH3, methyl, branching of R2, see Examiner’s Annotated Structure) and/or R2 is at a β-position to the oxygen atom to which R2 is bound (see Examiner’s Annotated Structure).
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Regarding claim 30, Prentice et al. in view of Shiraishi et al. teaches wherein each of R3, R4, R5, and R6 is H (R3, R4, R5, and R6 is H, see
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, Shiraishi [0059]), i.e., the compounds have the formula
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; or
wherein each of R4, R5, and R6 is H, and wherein R3 is C1-C6 alkyl (such as methyl or ethyl), i.e., the compounds have the formula
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(interpretation see 112b rejection above).
Regarding claim 31, Prentice et al. in view of Shiraishi et al. does not teach wherein m is 1.
Another example of Shiraishi et al. teaches wherein m is 1 (m = 1, see
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, the 9th example of generic formula (2) from the top, see [0051]).
It would have been obvious to one of ordinary skill in the art before the effective filling date of the claimed invention to modify Prentice et al. in view of Shiraishi et al. by adding the aliphatic diether
PNG
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105
805
media_image16.png
Greyscale
taught by Shiraishi et al. to have high heat resistance when A represents a CnH2n group of C5 to C9 (see Shiraishi [0049]).
Regarding claim 34, Prentice et al. in view of Shiraishi et al. teaches wherein the one or more dielectric compounds is present in an amount in the range of 50 wt% to 99.9 wt% (65 wt% to 99.9 wt%, Prentice [0078]).
Regarding claim 35, Prentice et al. in view of Shiraishi et al. teaches wherein the thermal management fluid has a flash point of at least 140 °C (flash point of at least 150 °C, see Prentice [0105]), measured in accordance with ASTM D93.
Regarding claim 36, Prentice et al. in view of Shiraishi et al. teaches wherein the thermal management fluid has a kinematic viscosity at 40 °C in the range of 1.5 to 20 cSt (kinematic viscosity at 40 °C of 1.5 to 20 cSt, see Prentice [0053]), all as measured in accordance with ASTM D455.
Regarding claim 37, it further requires a structure with three components A, B and C as illustrated.
PNG
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318
612
media_image17.png
Greyscale
Prentice et al. in view of Shiraishi et al. teaches wherein the one or more compounds of formula (I) have a similar structure, which differs in that B is different from B’ as illustrated.
PNG
media_image18.png
266
712
media_image18.png
Greyscale
(first concrete example of generic formula (4), Shiraishi [0059].)
in which each of Ra and Rb is independently methyl or ethyl and each of Rc and Rd is independently C3-C8 alkyl (Ra and Rb is methyl; Rc and Rd is C4 alkyl, -C4H9,
PNG
media_image19.png
334
1079
media_image19.png
Greyscale
), such as C3-C7 alkyl or C3-C6 alkyl (interpretation see 112b rejection above).
Prentice et al. in view of Shiraishi et al. does not teach B:
PNG
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249
249
media_image20.png
Greyscale
Another example of Shiraishi et al. teaches
PNG
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257
258
media_image21.png
Greyscale
(see
PNG
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411
871
media_image22.png
Greyscale
, m = 2, Shiraishi [0058])
It would have been obvious to one of ordinary skill in the art before the effective filling date of the claimed invention to substitute the
PNG
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124
507
media_image23.png
Greyscale
taught by Prentice et al. in view of Shiraishi et al. with the
PNG
media_image24.png
300
600
media_image24.png
Greyscale
taught by Shiraishi to have a branched-chain structure for an excellent balance in performance (see Shiraishi [0057]).
Regarding claim 39, it further requires a structure with three components A, B and C as illustrated.
PNG
media_image25.png
369
694
media_image25.png
Greyscale
Prentice et al. in view of Shiraishi et al. teaches wherein the one or more compounds of formula (I) have a similar structure, which differs in that B is different from B’ as illustrated.
PNG
media_image26.png
317
848
media_image26.png
Greyscale
(first concrete example of generic formula (4), Shiraishi [0059].)
in which each of Ra and Rb is independently methyl or ethyl and each of Rc and Rd is independently C3-C8 alkyl (Ra and Rb is methyl; Rc and Rd is C4 alkyl, -C4H9,
PNG
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348
1126
media_image27.png
Greyscale
), such as C3-C7 alkyl or C3-C6 alkyl (interpretation see 112b rejection above).
Prentice et al. in view of Shiraishi et al. does not teach B:
PNG
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227
379
media_image28.png
Greyscale
Shiraishi et al. teaches a branched-chain structure (see X, Y, Z in
PNG
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73
314
media_image29.png
Greyscale
[0053]).
It would have been obvious to one of ordinary skill in the art before the effective filling date of the claimed invention to modify the B’:
PNG
media_image23.png
124
507
media_image23.png
Greyscale
taught by Prentice et al. in view of Shiraishi et al. to be the branched-chain structure taught by Shiraishi et al. because the branched-chain structure is for an excellent balance in performance (see Shiraishi [0057]).
However, Prentice et al. in view of Shiraishi et al. is silent for a specific branched-chain structure for -C4H8-.
Due to structure limitation of branched-chain structure of -C4H8-O-, there are only eight possible structures:
PNG
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477
1397
media_image30.png
Greyscale
Therefore, for a person having ordinary skill in the art at the time of invention, it would have been obvious to try the structure 1
PNG
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206
359
media_image31.png
Greyscale
as it is one of only 8 alternatives, with the expected result that the benefit taught by Shiraishi et al. for branched structure would be achieve (MPEP 2141 III).
Regarding claim 40, it further requires a structure with three components A, B and C as illustrated.
PNG
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376
809
media_image32.png
Greyscale
Prentice et al. in view of Shiraishi et al. teaches wherein the one or more compounds of formula (I) have a similar structure, which differs in that B is different from B’ as illustrated.
PNG
media_image26.png
317
848
media_image26.png
Greyscale
(first concrete example of generic formula (4), Shiraishi [0059].)
in which each of Ra and Rb is independently methyl or ethyl and each of Rc and Rd is independently C3-C8 alkyl (Ra and Rb is methyl; Rc and Rd is C4 alkyl, -C4H9,
PNG
media_image27.png
348
1126
media_image27.png
Greyscale
), such as C3-C7 alkyl or C3-C6 alkyl (interpretation see 112b rejection above).
Prentice et al. in view of Shiraishi et al. does not teach B:
PNG
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189
351
media_image33.png
Greyscale
Shiraishi et al. teaches a branched-chain structure (see X, Y, Z in
PNG
media_image29.png
73
314
media_image29.png
Greyscale
[0053]).
It would have been obvious to one of ordinary skill in the art before the effective filling date of the claimed invention to modify the B’:
PNG
media_image23.png
124
507
media_image23.png
Greyscale
taught by Prentice et al. in view of Shiraishi et al. to be the branched-chain structure taught by Shiraishi et al. because the branched-chain structure is for an excellent balance in performance (see Shiraishi [0057]).
However, Prentice et al. in view of Shiraishi et al. is silent for a specific branched-chain structure for -C4H8-.
Due to structure limitation of branched-chain structure of -C4H8-O-, there are only eight possible structures:
PNG
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485
1419
media_image34.png
Greyscale
Therefore, for a person having ordinary skill in the art at the time of invention, it would have been obvious to try the structure 2
PNG
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222
427
media_image35.png
Greyscale
as it is one of only 8 alternatives, with the expected result that the benefit taught by Shiraishi et al. for branched structure would be achieve (MPEP 2141 III).
Claims 32-33 and 38 are rejected under 35 U.S.C. 103 as being unpatentable over Prentice et al. (WO 2020007954 A1, citations see machine translation filed on 4/15/2026) in view of Shiraishi et al. (US 20060171613 A1, provided on IDS filed on 8/24/2023) in view of Iwamoto et al. (JP 2005084074 A, provided on IDS filed on 8/24/2023).
Regarding claim 32, Prentice et al. in view of Shiraishi et al. does not teach wherein the one or more compounds of formula (I) have the structure
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222
569
media_image36.png
Greyscale
in which each of Ra and Rb is independently methyl or ethyl, and each of Rc and Rd is independently C3-C8 alkyl, such as C3-C7 alkyl or C3-C6 alkyl.
Iwamoto et al. teaches wherein the one or more compounds of formula (I) have the structure
PNG
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222
569
media_image36.png
Greyscale
(ST-IV-5, m =1; see
PNG
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67
314
media_image37.png
Greyscale
, when I10 = 1, R114 and R115 is
PNG
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100
182
media_image38.png
Greyscale
,[0241])
in which each of Ra and Rb is independently methyl or ethyl, and each of Rc and Rd is independently C3-C8 alkyl (Ra and Rb is ethyl; Rc and Rd is C4 alkyl, -C4H9, see
PNG
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100
182
media_image38.png
Greyscale
), such as C3-C7 alkyl or C3-C6 alkyl (interpretation see 112b rejection above).
It would have been obvious to one of ordinary skill in the art before the effective filling date of the claimed invention to modify Prentice et al. in view of Shiraishi et al. by adding the ST-IV-5 taught by Iwamoto et al. because the structure of ST-IV-5 is known in the art (see ST-IV-5, Iwamoto [0241]).
Regarding claim 33, Prentice et al. in view of Shiraishi et al. does not teach wherein the one or more dielectric compounds are independently selected from:
PNG
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1027
991
media_image39.png
Greyscale
Iwamoto et al. teaches wherein the one or more dielectric compounds (ST-IV-5,
PNG
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147
434
media_image40.png
Greyscale
, [0241]) are independently selected from:
PNG
media_image41.png
1027
1001
media_image41.png
Greyscale
It would have been obvious to one of ordinary skill in the art before the effective filling date of the claimed invention to modify Prentice et al. in view of Shiraishi et al. by adding the ST-IV-5 taught by Iwamoto et al. because the structure of
PNG
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147
434
media_image40.png
Greyscale
is known in the art (see ST-IV-5, Iwamoto [0241]).
Regarding claim 38, Prentice et al. in view of Shiraishi et al. does not teach wherein the one or more compounds of formula (I) have the structure
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179
578
media_image42.png
Greyscale
in which each of Ra and Rb is independently methyl or ethyl, and each of Rc and Rd is independently C3-C8 alkyl, such as C3-C7 alkyl or C3-C8 alkyl.
Iwamoto et al. teaches wherein the one or more compounds of formula (I) have the structure
PNG
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184
595
media_image43.png
Greyscale
(ST-IV-49, m =1; see
PNG
media_image44.png
48
275
media_image44.png
Greyscale
, when m10 = 3, R116 and R117 is
PNG
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100
182
media_image38.png
Greyscale
,[0245])
in which each of Ra and Rb is independently methyl or ethyl, and each of Rc and Rd is independently C3-C8 alkyl (Ra and Rb is ethyl; Rc and Rd is C4 alkyl, -C4H9, see
PNG
media_image38.png
100
182
media_image38.png
Greyscale
), such as C3-C7 alkyl or C3-C8 alkyl (interpretation see 112b rejection above).
It would have been obvious to one of ordinary skill in the art before the effective filling date of the claimed invention to modify Prentice et al. in view of Shiraishi et al. by adding the ST-IV-49 taught by Iwamoto et al. because the structure of ST-IV-49 is known in the art (see ST-IV-5, Iwamoto [0241]).
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
(RIEMSCHNEIDER): US-2973388-A, (2) in col. 2, lines 2-9;
(Prentice): US 20220228047 A1, Figs 1, 2, 3A and 3B;
(Pearson): US 20210362580 A1.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to NING CHEN whose telephone number is (571)272-1163. The examiner can normally be reached 9:30 AM - 4:30 PM.
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/NING CHEN/Examiner, Art Unit 1723 /TIFFANY LEGETTE/Supervisory Patent Examiner, Art Unit 1723
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