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 .
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 06/30/2025 has been entered.
This action is responsive to Applicant’s request for continued examination and amendment/remarks filed 06/30/2025 and the supplemental response filed 10/29/2025.
The supplemental response filed 10/29/2025 is entered.
Claims 1 and 3-14 are currently pending.
The rejection of claim 3 under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite is withdrawn in view of Applicant’s clarifying remarks. To recap the 112 issue of record, the prior Office action rejected claim 3 as indefinite regarding the antecedent basis of the “the monoalcohol” and “the fatty acid” because parent claim 1 contains more than one distinct monoalcohol (the monoalcohol fatty acid ester is obtainable by esterification of “a monoalcohol” and the diester is also obtainable by esterification of “a monoalcohol”) and more than one distinct fatty acid (the monoalcohol fatty acid ester is obtainable by esterification of “a fatty acid” and the diester is also obtainable by esterification of “fatty acids”) such that it was unclear which monoalcohol and fatty acid claim 3 was referring to. However, on page 4 of the response filed 10/29/2025 Applicant clarified the construction that the monoalcohol and the fatty acid refer to either monoalcohol or fatty acid of the monoalcohol fatty acid ester component (made from esterification of a monoalcohol and a fatty acid) and diester component (made from esterification of a diol with fatty acids or esterification of a monoalcohol with a dicarboxylic acid) is correct. Thus, the claim is merely broad, and breadth is not indefiniteness. See MPEP 2173.04, In re Miller, 441 F.2d 689, 169 USPQ 597 (CCPA 1971), and In re Gardner, 427 F.2d 786, 788, 166 USPQ 138, 140 (CCPA 1970).
The rejection of claim 13 under 35 U.S.C. 102(a)(1,2) and/or 35 U.S.C. 103 over Dance et al. (US 2020/0199430 A1) is withdrawn in view of the above amendment(s) amending claim 13 to be entirely dependent on claim 11.
The rejection(s) of claims 8 and 10-14 under 35 U.S.C. 103 as being unpatentable over Champagne (US 2022/0131205 A1) is/are withdrawn in view of the above amendment(s) amending claim 13 to be dependent on claim 11 and the new 132 Declaration filed 10/29/2025. See the Allowable Subject Matter section, below.
However, the rejection of claims 1, 3-7, and 9 under 35 U.S.C. 103 as being unpatentable over Champagne (US 2022/0131205 A1) as previously set forth in the Final Office action mailed 03/31/2025 is maintained and has been reiterated below. Note that the scope of these claims remain unchanged from that finally rejected and are not commensurate in scope with the comparative data of record. See the revised rejection and response to arguments, below.
Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claims 1, 3-7, and 9 are rejected under 35 U.S.C. 103 as being unpatentable over Champagne (US 2022/0131205 A1). Note that Champagne was also earlier published as WO 2020/182718 A1, which is an IDS reference.
As to claims 1 and 9, Champagne teaches cooling compositions suitable for cooling the battery or electronics of an electric vehicle or a hybrid vehicle comprising at least one ester (abstract). See also para. 0051-0052 and 0216-0217. The disclosure of “at least one ester” means there can be two esters. See also para. 0157 teaching there may be a mixture of two esters according to those defined in the disclosure. The term “ester” is defined in the reference as including monoester and diester (para. 0015). The monoester is preferably a branched monoester formed from reacting a monocarboxylic acid, preferably one with a saturated and branched hydrocarbon-based chain, with a monoalcohol including a linear or branched saturated hydrocarbon-based chain (para. 0024). See also para. 0038 further clarifying preferred chain lengths of the monocarboxylic acid forming the monoester and encompass fatty acid as claimed. The monoester is a monoalcohol fatty acid as claimed.
Champagne’s monoester is a monoalcohol fatty acid ester that is obtainable/obtained from esterification of a monoalcohol with a fatty acid (Id.). The monoalcohol preferably comprises 1 to 14 carbon atoms and subsets thereof and the fatty acid (monocarboxylic acid) preferably comprises 1 to 14 carbon atoms and subsets thereof (para. 0038 and 0078), which overlaps the claimed ranges of monoalcohol carbon atoms being between 5 and 8 carbon atoms and fatty acid carbon atoms being between 12 and 18 carbon atoms.
Champagne further teaches the diester may be formed from a dicarboxylic acid and a monoalcohol or from a monocarboxylic acid and a diol (para. 0065).
Champagne discloses various embodiments of chemical formulae for the ester beginning at para. 0110. One preferred formula is G1-C(O)-O-G2 (para. 0114), and a preferred embodiment thereof includes 1) G1 representing a group R1-O-C(O)-A1- where a) A1 represents an alkylene group preferably of 2 to 12 carbon atoms and b) R1 represents a linear or branched, saturated or unsaturated hydrocarbon-based chain preferably of 1 to 13 carbon atoms, and 2) G2 representing a linear or branched alkyl chain of preferably 1 to 14 carbon atoms (para. 0118-0119 that references para. 0116 for the meaning of R1). Also note the reference’s definition for “hydrocarbon-based chain” at para. 0076 that describe preferred subsets of chain lengths and also includes a sub-definition that alkylene chains may be linear or branched and saturated or unsaturated. These embodiments of para. 0118-0119 describe and encompass a diester obtainable from esterification of a monoalcohol with a dicarboxylic acid, and the sum of the carbon atoms from the formula, G1, A1, R1, and G2 groups overlap and encompass the claimed 19 to 26 carbon atom range.
Alternatively, another preferred embodiment of the above formula of para. 0114 includes 1) G1 representing an alkyl group of preferably 3 to 14 carbon atoms, and 2) G2 representing a group -A2-O-C(O)-R2 where a) A2 represents an alkylene group preferably of 1 to 13 carbon atoms and b) R2 represents a linear or branched, saturated or unsaturated hydrocarbon-based chain preferably of 3 to 13 carbon atoms (para. 0118-0119 that references para. 0116 for the meaning of R2). Again, also note the reference’s definition for “hydrocarbon-based chain” at para. 0076. These embodiments of para. 0118-0119 describe and encompass a diester obtainable from esterification of a diol with fatty acids, and the sum of the carbon atoms from the formula, G1, G2, A2, and R2 groups overlap and encompass the claimed 19 to 26 carbon atom range.
While the reference fail to anticipate a combination of monoester and diester at weight ratios between 15/85 and 55/45 and 20/80 and 55/45, at the time of the effective filing date it would have been obvious to a person of ordinary skill in the art to formulate and arrive within the claimed limitations from the teachings of Champagne with a reasonable expectation of success since Champagne directly teach providing a mixture of esters, including monoester and diester, in order to obtain a composition suitable for cooling electronic devices. Regarding relative percentages, Champagne teach the esters according to their invention preferably contain certain kinematic viscosity and autoignition properties which ensures stability of the composition (abstract and para. 0043 & 0153-0156). At the time of the effective filing date it would have been obvious to a person of ordinary skill in the art to vary and tailor the relative amount of esters (e.g., monoester to diester) in the mixture of esters in order to obtain a sufficient/workable, if not optimal, balance of kinematic viscosity and autoignition properties in the composition with a reasonable expectation of success.
As to claims 3 and 6, Champagne’s monoester is a monoalcohol fatty acid ester that is obtainable/obtained from esterification of a monoalcohol with a fatty acid (Id.). The monoalcohol preferably comprises 1 to 14 carbon atoms and subsets thereof such as 3 to 14 and 5 to 12 (para. 0038 and 0078), which encompass isoamyl alcohol (a C5 monoalcohol composed of a branched, saturated hydrocarbon-based chain) and 2-ethylhexyl alcohol (a C8 monoalcohol composed of a branched, saturated hydrocarbon-based chain). The fatty acid (monocarboxylic acid) includes a linear or branched, saturated or unsaturated hydrocarbon-based chain, preferably of 1 to 14 carbon atoms and subsets thereof such as 3 to 14 and 5 to 12 (para. 0038 and 0078), which encompass caprylic acid (a C8 monocarboxylic acid composed of a linear, saturated hydrocarbon-based chain), capric acid (a C10 monocarboxylic acid composed of a linear, saturated hydrocarbon-based chain), and lauric acid (a C12 monocarboxylic acid composed of a linear, saturated hydrocarbon-based chain). These teachings and rationale encompass isoamyl laurate (a monoester made from esterifying isoamyl alcohol, a C5 monoalcohol composed of a branched, saturated hydrocarbon-based chain, with lauric acid, a C12 monocarboxylic acid composed of a linear, saturated hydrocarbon-based chain) and 2-ethylhexyl laurate (a monoester made from esterifying 2-ethylhexyl alcohol, a C8 monoalcohol composed of a branched, saturated hydrocarbon-based chain, with lauric acid, a C12 monocarboxylic acid composed of a linear, saturated hydrocarbon-based chain) as recited in claim 6 for the same reasons.
Alternatively regarding claim 3, building off what is already disclosed in Champagne regarding independent claim 1 (above), the prior-cited teachings of para. 0114, 0116, 0118, & 0119 and above-stated rationale encompass the monoalcohol forming the diester (Champagne teaches the diester may be formed from a dicarboxylic acid and a monoalcohol at para. 0065, Id.) being isoamyl alcohol (when both R1 and G2 are each a C5 saturated, branched alkyl chain) or 2-ethylhexyl alcohol (when both R1 and G2 are each a C8 saturated, branched alkyl chain). Furthermore, the prior-cited teachings of para. 0114, 0116, 0118, & 0119 and above-stated rationale encompass the monoalcohol forming the diester (Champagne teaches the diester may also be formed from a monocarboxylic acid, i.e., fatty acid, and a diol at para. 0065, Id.) being caprylic acid (when one or both of G1 and R2 are a C7 alkyl group forming at least one caprylate group), capric acid (when one or both of G1 and R2 are a C9 alkyl group forming at least one caprate group), and/or lauric acid (when one or both of G1 and R2 are a C11 alkyl group forming at least one laurate group). Note regarding caprylate being a C8 structure but represented as C7 in the reference’s formula, caprate being a C10 structure but represented as C9 in the reference’s formula, and laurate being a C12 structure but represented as C11 in the reference’s formula, this rationale amounts to the formula being G1-C(O)-O-A2-O-C(O)-R2, meaning there is an additional carbon bound to each of G1 and R2.
As to claims 4, 5, and 7, building off what is already disclosed in Champagne regarding independent claim 1 (above), the prior-cited teachings of para. 0114, 0116, 0118, & 0119 and above-stated rationale encompass the dicarboxylic acid being sebacic acid (when A1 is a C8 alkylene group; note, this amounts to a diacid length of 10 as the formula amounts to R1-O-C(O)-A1-C(O)-O-G2, with an additional carbon bound to both ends of A1) as recited in claim 5. These teachings and rationale also encompass the diester being di-2-ethylhexyl sebacate (when A2 is a C8 alkylene group and both R1 and G2 are each a C8 saturated, branched alkyl chain) as recited in claim 7.
Alternatively, the prior-cited teachings of para. 0114, 0116, 0118, & 0119 and above-stated rationale encompass the diol being propylene glycol (when A2 is a C3 alkylene group) as recited in claim 4. These teachings and rationale also encompass the diester being propylene glycol di-caprate/di-caprylate (when A2 is a C3 alkylene group and one or more of: 1) G1 and R2 are each a C7 alkyl group forming two caprylate groups, 2) G1 and R2 are each a C9 alkyl group forming two caprate groups, and/or 3) one of G1 or R2 is a C7 alkyl group forming a caprylate group and the other of G1 or R2 is a C9 alkyl group forming a caprate group; note regarding caprylate being a C8 structure but represented as C7 in the formula and caprate being a C10 structure but represented as C9 in the formula, this rationale amounts to the formula being G1-C(O)-O-A2-O-C(O)-R2, meaning there is an additional carbon bound to each of G1 and R2) as recited in claim 7.
Response to Arguments & Second Declaration of Ms. Marion Kerbrat
Applicant's arguments filed 06/302025 and 10/29/2025 regarding Champagne (US 2022/0131205 A1) have been fully considered but they are not persuasive.
Applicant argues the claims are directed to a liquid dielectric coolant comprising specific monoalcohol fatty acid esters and diesters within a specific ratio that possess a good compatibility with various materials whereas Champagne is broadly directed to various, possible compositions that fall outside the instant claims and does not teach, suggest, or hint that any specific combination of esters in a specific ratio will show good combability. Applicant provided a second declaration on 10/29/2025 that includes additional comparative data and the totality of data of record that they allege demonstrates criticality of the claimed weight ranges.
In the second declaration, pages 1 to 2 at ¶ 1 to 3 of the declaration provide a summary of Ms. Kerbrat’s background and a summary of the claimed invention and recent prosecution history. Pages 2 to 3 (¶ 4 to 6) of the declaration provide additional data and discussion thereof to accompany the examples in the original disclosure to allege the claimed combinations possess unexpected results and the claimed weight ratios thereof possess criticality. Page 4 of the declaration is a concluding statement and the declarant’s signature and date. Pages 5 to 10 the declaration is Exhibit A, which is merely a copy of the Interview Summary (and its Appendix) of record mailed 06/30/2025. Pages 11 and 12 of the declaration is Exhibit B, which is an updated summary of data submitted in the application to date (Exhibit B includes the data originally present in the specification as filed, the additional data submitted in the first declaration filed on 03/19/2025, and the new data introduced in this second declaration).
After careful and full consideration of its contents, the declaration under 37 CFR 1.132 filed 10/29/2025 is sufficient in-part to overcome the 103 rejection of record over Champagne. Specifically, the declaration is sufficient to overcome the 103 rejection of claims 8 and 10-14 over Champagne but is insufficient to overcome the 103 rejection of claims 1, 3-7, and 9 over Champagne.
Applicant has demonstrated by direct comparative showing that the recited pairs of specific monoalcohol fatty acid esters and diesters recited in claims 8 and 10 (1. isoamyl isostearate and propylene glycol di-caprate/di-caprylate, 2. isoamyl laurate and propylene glycol di-caprate/di-caprylate, and 3. 2-ethylhexyl laurate and di-2-ethylhexyl sebacate) unexpectedly possess a less than 20% change of volume of PVC immersed in the pairs/combinations when the specific monoalcohol fatty acid esters and diesters are within the specific weight ratio range between 15/85 and 55/45 compared to when they are outside the weight ratio range.
However, independent claim 1 and its rejected dependent claims are significantly more broad than the particular combinations in the comparative showings. Claims 1, 3-7, and 9 are not deemed patentable over the reference of record since they are not commensurate in scope with the probative value of data in the examples.
The totality of the comparative data of record amounts to three very particular blends of branched monoesters and diesters (1. isoamyl isostearate with propylene glycol di-caprate/di-caprylate, 2. Isoamyl laurate with propylene glycol di-caprate/di-caprylate, and 3. 2-ethylhexyl laurate with di-2-ethylhexyl sebacate) whereas independent claim 1 very broadly encompass much more of all combinations of 1. monoalcohol fatty acid (mono)esters whether branched or not obtained from esterifying a 5-8 carbon atom monoalcohol with a 12-18 carbon atom fatty acid and diesters having 19 to 26 carbon atoms obtained from esterifying any diol with any fatty acids (so long as a final diester has 19 to 26 carbon atoms) or 2. monoalcohol fatty acid (mono)esters whether branched or not obtained from esterifying a 5-8 carbon atom monoalcohol with a 12-18 carbon atom fatty acid and diesters having 19 to 26 carbon atoms obtained from esterifying any monoalcohol with any dicarboxylic acid (so long as a final diester has 19 to 26 carbon atoms). Also, while some dependent claims individually require one of the tested monoesters or one of the tested diesters, those dependent claims do not require the actual pair of tested monoester and diester (for example, claim 6 requires the monoalcohol fatty acid ester be isoamyl isostearate, isoamyl laurate, or 2-ethylhexyl laurate but does not require the respectively tested diester of the tested pairs, e.g., propylene glycol di-caprate/di-caprylate, propylene glycol di-caprate/di-caprylate, or di-2-ethylhexyl sebacate, respectively, and may contain any diester having 19 to 26 carbon atoms obtained from esterifying any diol with any fatty acids or obtained from esterifying any monoalcohol with any dicarboxylic acid so long as a final diester has 19 to 26 carbon atoms; similarly, claim 7 requires the diester be propylene glycol di-caprate/di-caprylate or di-2-ethylhexyl sebacate but does not require the respectively tested monoester of the tested pairs, e.g., isoamyl isostearate, isoamyl laurate, or 2-ethylhexyl laurate, respectively, and may contain any monoalcohol fatty acid (mono)ester whether branched or not obtained from esterifying a 5-8 carbon atom monoalcohol with a 12-18 carbon atom fatty acid).
The limited number of monoester+diester pairs exemplified do not provide an adequate basis for concluding that similar results would be obtained for the hundreds of other monoester+diester pairs encompassed within the scope of the broader claims. There is insufficient data to reasonably concluding that the great number and variety of monoester+diester pairs included in the claims would behave in the same manner as the three tested monoester+diester pairs. Applicant has also not provided evidence and a reasoned argument explaining why the three tested pairs are representative of the full scope of the claimed combination’s breadth. See In re Kollman, 595 F.2d 48, 201 USPQ 193 (CCPA 1979) and In re Lindner, 457 F.2d 506, 509, 173 USPQ 356, 359 (CCPA 1972).
Applicant’s arguments to Champagne set forth in the remarks filed on 06/30/2025 and 10/29/2025 are based on the declaration and the totality of data of record and are also not persuasive for the same reasons that the declaration is insufficient to withdraw the 103 rejection over Champagne.
In view of the foregoing, the rejection is maintained for the reasons of record.
Allowable Subject Matter
Claims 10-14 are allowed.
Claim 8 is objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
The following is a statement of reasons for the indication of allowable subject matter:
Applicant has demonstrated by direct comparative showing that the recited pairs of specific monoalcohol fatty acid esters and diesters (1. isoamyl isostearate and propylene glycol di-caprate/di-caprylate, 2. isoamyl laurate and propylene glycol di-caprate/di-caprylate, and 3. 2-ethylhexyl laurate and di-2-ethylhexyl sebacate) unexpectedly possess a less than 20% change of volume of PVC immersed in the pairs/combinations when the specific monoalcohol fatty acid esters and diesters are within the specific weight ratio range between 15/85 and 55/45 compared to when they are outside the weight ratio range. See Exhibit B of the 132 Declaration filed 10/29/2025 which helpfully shows the cumulative data of record.
Champagne (US 2022/0131205 A1) teaches cooling compositions suitable for cooling the battery or electronics of an electric vehicle or a hybrid vehicle comprising at least one ester (abstract). See also para. 0051-0052 and 0216-0217. The disclosure of “at least one ester” means there can be two esters. See also para. 0157 teaching there may be a mixture of two esters according to those defined in the disclosure. The term “ester” is defined in the reference as including monoester and diester (para. 0015). The monoester is preferably a branched monoester formed from reacting a monocarboxylic acid, preferably one with a saturated and branched hydrocarbon-based chain, with a monoalcohol including a linear or branched saturated hydrocarbon-based chain (para. 0024). See also para. 0038 and 0078 further clarifying preferred chain lengths of the monoalcohol and monocarboxylic acid forming the monoester. Champagne further teaches the diester may be formed from a dicarboxylic acid and a monoalcohol or from a monocarboxylic acid and a diol (para. 0065). See also para. 0110-0119 further clarifying preferred chain lengths of the components forming the diester. However, complimenting Applicant’s evidence of criticality/unexpected results of the recited pairs/concentrations (Id.), Champagne fails to teach or suggest the three recited pairs of specific monoalcohol fatty acid esters and diesters (1. isoamyl isostearate and propylene glycol di-caprate/di-caprylate, 2. isoamyl laurate and propylene glycol di-caprate/di-caprylate, and 3. 2-ethylhexyl laurate and di-2-ethylhexyl sebacate).
The remaining references listed on Forms 892 and 1449 have been reviewed by the examiner and are considered to be cumulative to or less material than the prior art references relied upon or described above.
Correspondence
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/MATTHEW R DIAZ/Primary Examiner, Art Unit 1761
/M.R.D./
January 26, 2026