DETAILED ACTION
Response to Amendment
Claims 20-23 and 34-37 are currently pending. Claims 1-19, 24-33, 38, and 39 are cancelled. The amended claims do overcome the previously stated 103 rejections. However, upon further consideration, claims 20-23 and 34-37 are rejected under the following new 103 rejections.
Information Disclosure Statement
The information disclosure statement (IDS) submitted on 9/29/25 was filed after the mailing date of the Non-Final Rejection on 7/25/25. The submission is in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statement is being considered by the examiner.
Claim Rejections - 35 USC § 103
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.
Claims 20-23 and 34-37 are rejected under 35 U.S.C. 103 as being unpatentable over Claeys et al (US 2012/0164506) in view of Tsubouchi (US 2012/0283162), Okido et al (US 10,723,926), and further in view of Takahashi et al (US 2017/0327765).
Regarding claims 20, 21, 23, and 34-37, Claeys et al discloses a method of cooling an electric drive systems (propulsion system), the method comprising cooling a battery and electric motor cooling loop of an electric vehicle using a composition comprising: an ester-based heat transfer fluid and conventional additives such as corrosion inhibitors (anticorrosion agents) and oxidative stability additive (antioxidants); wherein the heat transfer fluid has low flammability which would correspond to high auto-ignition temperature; wherein the ester based coolant has all the physical characteristics suitable for use in an electric vehicle, including viscosity (kinematic viscosity, measured according to standard ASTM D445) and pour point ([0009]-[0012],[0016],[0061]-[0063]).
However, Claeys et al does not expressly teach an ester having a kinematic viscosity, measured at -25°C according to the standard ASTM D445, of less than or equal to 200 mm2/s; wherein the ester is a monoester formed from: a saturated branched monocarboxylic acid; and a saturated branched monoalcohol (claims 20 and 35); wherein the composition comprises at least 30% by mass of the ester (claim 21); wherein the ester has a kinematic viscosity, measured at -25°C according to the standard ASTM D445, of less than or equal to 150 mm2/s (claims 23 and 36).
Tsubouchi discloses a base oil (composition) for cooling a device that includes 30 mass% or more, or further preferably 70 mass% or more, of a monoester, and the base oil has a kinematic viscosity at 40°C in a range of 4 mm2/s to 30 mm2/s; wherein the device is usable for an electric vehicle or a hybrid vehicle; wherein the device is at least one of a motor and a battery ([0009]); wherein the ester is obtainable by a dehydro-condensation reaction between a carboxylic acid and an alcohol, the alcohol (the starting material) having a long linear alkyl chain and a carboxylic acid (the starting material) having a long linear alkyl chain that are preferably used for synthetic reaction such that the total number of the terminal methyl group, the methylene group and the ether group in the main chain (i.e., the longest chain in a molecule) is 18 or more and the total number of a short alkyl side chain in the molecule (i.e., the methyl branch and the ethyl branch) is 2 or less; wherein examples of the carboxylic acid include
monocarboxylic acids such as ethylhexanoate (saturated branched monocarboxylic
acid); wherein examples of the alcohol include monoalcohol such as ethylhexanol (saturated branched monoalcohol), .... ([0016],[0065]-[0076]). Examiner’s note: although Tsubouchi does not explicitly teach a kinematic viscosity measured at -25°C, based upon the relationship between the kinematic viscosity at -25°C (less than or equal to 200 mm2/s) and the kinematic viscosity at 25°C (less than equal to 20 mm2/s), one of ordinary skill in the art would expect a kinematic viscosity at 40°C of 4 mm2/s to 30 mm2/s to inherently correspond to a kinematic viscosity at -25°C of less than or equal to 200 mm2/s, or less than or equal to 150 mm2/s.
Therefore, it would have been obvious to one of ordinary skill in the art at the time the invention was made to modify the Claeys ester-based heat transfer fluid to include ester that has a kinematic viscosity, measured at -25°C according to the standard ASTM D445, of less than or equal to 150 mm2/s; wherein the monoester is formed from: a monocarboxylic acid such as ethylhexanoate; and a monoalcohol such as ethylhexanol; wherein the composition comprises at least 70% by mass of the ester, based on the total weight of the composition in order to provide a base oil having excellent electrical insulation properties and thermal conductivity for cooling a device ([0010]).
However, Claeys et al as modified by Tsubouchi does not expressly teach an ester that is a monoester formed from: a saturated branched C9 monocarboxylic acid; and a saturated branched C9 monoalcohol (claims 20 and 35).
Okido et al discloses a working fluid composition for a refrigerating machine comprising a refrigerating machine oil comprising a second ester comprising a constituent comprising at least one selected from the group consisting of 2-ethylhexanol and 3,5,5-trimethylhexanol (saturated branched C9 monoalcohol), and a constituent fatty acid comprising at least one selected from the group consisting of 2-ethylhexanoic acid and 3,5,5-trimethylhexanoic acid (saturated branched C9 monocarboxylic acid) (claim 9).
Therefore, it would have been obvious to one of ordinary skill in the art at the time the invention was made to modify the Claeys/Tsubouchi ester-based heat transfer fluid to include a monoester is formed from: 3,5,5-trimethylhexanoic acid and 3,5,5-trimethylhexanol in order to utilize a refrigerating machine oil that is excellent in refrigerant compatibility and lubricity (col. 9, lines 50-53).
However, Claeys et al as modified by Tsubouchi and Okido et al does not expressly teach an ester having an auto-ignition temperature, measured according to the standard ASTM E659, of greater than or equal to 350°C (claims 20 and 35); wherein the ester has an auto-ignition temperature, measured according to the standard ASTM E659, of greater than or equal to 360°C (claim 23 and 36).
Takahashi et al discloses the spontaneous ignition point (auto-ignition temperature) of an ester based oil that is in light of improving flame retardancy (low flammability), preferably 350°C or more, more preferably 360°C, measured by the method in accordance with ASTM E659 ([0025]).
Therefore, it would have been obvious to one of ordinary skill in the art at the time the invention was made to modify the Claeys/Tsubouchi/Okido ester-based heat transfer fluid to include an ester having an auto-ignition temperature, measured according to the standard ASTM E659, of greater than or equal to 360°C in order to improve the flame retardancy of the heat transfer fluid ([0025]).
Regarding claim 22, the Office takes the position that a lithium-ion battery of an electric or hybrid vehicle is well known in the art.
Claims 35-37 are rejected under 35 U.S.C. 103 as being unpatentable over Koga (US 2016/0201002) in view of Tsubouchi (US 2012/0283162), and further in view of Okido et al (US 10,723,926).
Regarding claims 35-37, Koga discloses a lubricating oil composition (composition) that is prepared by blending a base oil (ester) and an antioxidant, wherein an example of the base oil is 3,5,5-trimethylhexanoic acid 3,5,5-trimethylhexyl ester; wherein the composition comprises 91.25 mass% of the ester ([0011],[0083] and Table 1, Example 18). Examiner’s note: the limitation “for cooling a propulsion system of an electric or hybrid vehicle” is construed as being intended use. Since the Koga lubricating oil composition is inherently capable of performing the function, it reads on the claim.
However, Koga does not expressly teach an ester having a kinematic viscosity, measured at -25°C according to the standard ASTM D445, of less than or equal to 200 mm2/s; wherein the ester is a monoester formed from: a saturated branched monocarboxylic acid; and a saturated branched monoalcohol; wherein the composition comprises more than 95% by mass of the ester, relative to the total mass of the composition (claim 35); wherein the ester has a kinematic viscosity, measured at -25°C according to the standard ASTM D445, of less than or equal to 150 mm2/s (claim 36).
Tsubouchi discloses a base oil (composition) for cooling a device that includes 30 mass% or more, or further preferably 70 mass% or more, of a monoester, and the base oil has a kinematic viscosity at 40°C in a range of 4 mm2/s to 30 mm2/s; wherein the device is usable for an electric vehicle or a hybrid vehicle; wherein the device is at least one of a motor and a battery ([0009]); wherein the ester is obtainable by a dehydro-condensation reaction between a carboxylic acid and an alcohol, the alcohol (the starting material) having a long linear alkyl chain and a carboxylic acid (the starting material) having a long linear alkyl chain that are preferably used for synthetic reaction such that the total number of the terminal methyl group, the methylene group and the ether group in the main chain (i.e., the longest chain in a molecule) is 18 or more and the total number of a short alkyl side chain in the molecule (i.e., the methyl branch and the ethyl branch) is 2 or less; wherein examples of the carboxylic acid include
monocarboxylic acids such as ethylhexanoate (saturated branched monocarboxylic
acid); wherein examples of the alcohol include monoalcohol such as ethylhexanol (saturated branched monoalcohol), .... ([0016],[0065]-[0076]). Examiner’s note: although Tsubouchi does not explicitly teach a kinematic viscosity measured at -25°C, based upon the relationship between the kinematic viscosity at -25°C (less than or equal to 200 mm2/s) and the kinematic viscosity at 25°C (less than equal to 20 mm2/s), one of ordinary skill in the art would expect a kinematic viscosity at 40°C of 4 mm2/s to 30 mm2/s to inherently correspond to a kinematic viscosity at -25°C of less than or equal to 200 mm2/s, or less than or equal to 150 mm2/s.
Therefore, it would have been obvious to one of ordinary skill in the art at the time the invention was made to modify the Koga base oil to include ester that has a kinematic viscosity, measured at -25°C according to the standard ASTM D445, of less than or equal to 150 mm2/s; wherein the monoester is formed from: a monocarboxylic acid such as ethylhexanoate; and a monoalcohol such as ethylhexanol; wherein the composition comprises at least 70% by mass of the ester, based on the total weight of the composition in order to provide a base oil having excellent electrical insulation properties and thermal conductivity for cooling a device ([0010]). In addition, it would have been obvious to one of ordinary skill in the art at the time the invention was made to modify the Koga/Tsubouchi base oil to include more than 95% by mass of the ester, relative to the total mass of the composition because it has been held that the discovery of an optimum value of a result effective variable in a known process is ordinarily within the skill of the art. In re Boesch, 205 USPQ 215 (CCPA 1980). Where the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation. In re Aller, 220 F.2d 454. 456, 105 USPQ 233, 235 (CCPA 1955)). There is no evidence of criticality of the claimed composition of the ester.
However, Koga as modified by Tsubouchi does not expressly teach an ester having a kinematic viscosity, measured at -25°C according to the standard ASTM D445, of less than or equal to 200 mm2/s; wherein the ester is a monoester formed from: a saturated branched C9 monocarboxylic acid; and a saturated branched C9 monoalcohol (claims 20 and 35); wherein the composition comprises at least 30% by mass of the ester (claim 21); wherein the ester has a kinematic viscosity, measured at -25°C according to the standard ASTM D445, of less than or equal to 150 mm2/s (claims 23 and 36).
Okido et al discloses a working fluid composition for a refrigerating machine comprising a refrigerating machine oil comprising a second ester comprising a constituent comprising at least one selected from the group consisting of 2-ethylhexanol and 3,5,5-trimethylhexanol (saturated branched C9 monoalcohol), and a constituent fatty acid comprising at least one selected from the group consisting of 2-ethylhexanoic acid and 3,5,5-trimethylhexanoic acid (saturated branched C9 monocarboxylic acid); wherein the content of the second ester is 5 to 40% by mass based on the total amount of the refrigerating machine oil; wherein the second ester inherently has a kinematic viscosity at -25°C of less than or equal to 200 mm2/s, or less than or equal to 150 mm2/s (claim 9).
Therefore, it would have been obvious to one of ordinary skill in the art at the time the invention was made to modify the Koga/Tsubouchi ester-based heat transfer fluid to include ester that has a kinematic viscosity, measured at -25°C according to the standard ASTM D445, of less than or equal to 150 mm2/s; wherein the monoester is formed from: 3,5,5-trimethylhexanoic acid and 3,5,5-trimethylhexanol; wherein the composition comprises at least 30% by mass of the ester, based on the total weight of the composition in order to utilize a refrigerating machine oil that is excellent in refrigerant compatibility and lubricity (col. 9, lines 50-53). In addition, the limitation “an auto-ignition temperature of greater than or equal to 360°C” is an inherent characteristic of the Koga/Tsubouchi/Okido base oil because Koga as modified by Tsubouchi and Okido et al teaches the same monoester as the present invention.
Response to Arguments
Applicant's arguments filed 11/25/25 have been fully considered but they are not persuasive.
The Applicant argues that “While Okido discloses examples that include 3,5,5-trimethylhexanoic acid and 3,5,5-trimethylhexanol alcohol, Okido fails to disclose or suggest using these compounds to form ester. In fact, the ester (B) may be an ester formed from at least one polyhydric alcohol, a polybasic acid, and a monohydric alcohol when carboxyl groups remain in the intermediate compound, i.e. at the end of the reaction between the polyhydric alcohol and the polybasic acid, or alternatively an ester formed from at least one polyhydric alcohol, a polybasic acid, and a fatty acid when hydroxyl groups remain in the intermediate compound. Okido, col. 6, lines 21 to 34.
Therefore, none of the esters described of exemplified in Okido contain both a monohydric alcohol and a monocarboxylic acid, and such an ester is not suggested in this document. Consequently, none of the esters described or exemplified in Okido are esters as recited in at least amended claims 20 and 35. Therefore, the person skilled in the art, starting from Claeys and taking the teaching of Okido would not arrive to the presently claimed monoester, since neither reference discloses nor suggests such a monoester”.
In response to applicant's arguments against the references individually, one cannot show nonobviousness by attacking references individually where the rejections are based on combinations of references. See In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981); In re Merck & Co., 800 F.2d 1091, 231 USPQ 375 (Fed. Cir. 1986). As stated in the 103 rejections above, Tsubouchi teaches a monoester that is obtainable by a dehydro-condensation reaction between a carboxylic acid and an alcohol, wherein examples of the carboxylic acid include monocarboxylic acids such as ethylhexanoate (saturated branched monocarboxylic acid); and wherein examples of the alcohol include monoalcohol such as ethylhexanol (saturated branched monoalcohol). Even if Okido does not explicitly teach an ester that is formed from a monocarboxylic acid and a monoalcohol, one of ordinary skill in the art would have recognized that 3,5,5-trimethylhexanol (saturated branched C9 monoalcohol) and 3,5,5-trimethylhexanoic acid (saturated branched C9 monocarboxylic acid) taught by Okido are suitable compounds for forming the monoester taught by Tsubouchi and the substitution of one known saturated branched monoalcohol and saturated branched monocarboxylic acid for another would have yielded predictable results to one of ordinary skill in the art at the time of the invention.
The Applicant further argues that “contrary to the assertion of the Examiner’s, there is no evidence that Takahashi’s disclosure with respect to spontaneous ignition point of an ester base oil of Formula 1 is relevant a monoester as recited in claims 20 and 35. On the contrary, Takahashi teaches that larger esters are required in order to provide the desired heat transfer properties”.
In response, Takahashi is relied upon for teaching a spontaneous ignition point (auto-ignition temperature) of an ester based oil that is preferably 350°C or more, more preferably 360°C, measured by the method in accordance with ASTM E659. Based upon this teaching, it would have been obvious to one of ordinary skill in the art to optimize the Claeys/Tsubouchi/Okido ester-based heat transfer fluid composition to include an auto-ignition temperature of 350°C or more in order to improve the flame retardancy of the heat transfer fluid.
Conclusion
THIS ACTION IS MADE FINAL. Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
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/T.S.C/Examiner, Art Unit 1751
/JONATHAN G LEONG/Supervisory Patent Examiner, Art Unit 1751 12/16/2025