DETAILED ACTION
Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Status of the Claims
Claims 1-20 are pending and examined.
Claim of Foreign Priority
Applicant’s claim of foreign priority is acknowledged. However, an English translation of the foreign priority document does not appear to have been provided. As such, priority has not been perfected.
Claim Objection
Claim 5 is objected to for a lack of clarity. It recites: “wherein the…in step (1) have a mass ratio of is (10-20):1.” It appears to refer to a mass ratio of 10-20:1. Further, Applicant appears to mean that the ratio of non-aqueous solvent to lithium hexafluorophosphate is 10-20:1. Clarification is requested.
Claim Rejections - 35 USC § 112
Claims 1-7, 9, 10 and 16-20 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. It is not clear where the line of demarcation is between a poor and a non-poor solvent. Poor solvent is not defined in the instant Specification. Claim 8 is not rejected because it species solvents. As such, to obviate this rejection Applicant can incorporate the limitations of claim 8 into claim 1.
Claims 6 and 8: A broad range or limitation together with a narrow range or limitation that falls within the broad range or limitation (in the same claim) may be considered indefinite if the resulting claim does not clearly set forth the metes and bounds of the patent protection desired. See MPEP § 2173.05(c). In the present instance, claims 6 and 8 recite the broad recitation “any one,” and the claim also recites “or a combination of at least two” which is the narrower statement of the range/limitation. The claim(s) are considered indefinite because there is a question or doubt as to whether the feature introduced by such narrower language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claims.
Claim Rejections - 35 USC § 102
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.
Claims 10-15 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Zhao et al., (CN110845539A) (cited in ISR).
Zhao teaches a battery-grade lithium difluorobis (oxalato) phosphate solid. The chloride ion content is 10 ppm or less and the moisture and oxygen content is less than 1 ppm. In Example 2, the chloride ion content was 3.5 ppm and in Example 4, the chloride ion content was 1.9 ppm. The solid component is part of a electrolyte component and battery additive. These electrolytes are often components in lithium-ion batteries. The process does not appear to yield a metal ion impurity content that is greater than 10 ppm, absent evidence to the contrary.
“[E]ven though product-by-process claims are limited by and defined by the process, determination of patentability is based on the product itself. The patentability of a product does not depend on its method of production. If the product in the product-by-process claim is the same as or obvious from a product of the prior art, the claim is unpatentable even though the prior product was made by a different process.” In re Thorpe, 777 F.2d 695, 698, 227 USPQ 964, 966 (Fed. Cir. 1985) (citations omitted). See M.P.E.P. § 2113.
As such, claims 10-15 are anticipated by the cited prior art.
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 1-20 are rejected under 35 U.S.C. 103 as being unpatentable over Feng et al., (CN110204576A) (published September 6, 2019), in view of Kondo et al., (WO2013187380A1), and in view of Morinaka et al., (EP2857406 B1).
Feng teaches a method for preparing a solution comprising lithium difluorobis oxalate phosphate. It is mainly used as an additive for a nonaqueous electrolyte battery or lithium ion capacitor. Specific steps comprise reacting oxalyl chloride in a non-aqueous solvent to obtain a solution. Reaction temperatures for the steps range from 50 to 90°C to 30 to 80°C. Each of these ranges overlap those claimed and this is an optimizable parameter. See below. To the above-described solution lithium hexafluorophosphate is added and reacted to obtain the lithium difluorobis oxalate phosphate solution. The non-aqueous solvent to be used includes: diethyl carbonate, ethyl methyl carbonate, ethyl acetate and more. The non-aqueous solvent has a water content of less than 10 ppm. The steps can be performed under an inert gas atmosphere and stirring and performing acid removal are contemplated. Chloride ions were limited to 3.2 ppm as measured. Filtration out of insoluble substances is contemplated in an inert gas, including nitrogen, argon, and helium.
Feng does not teach adding siloxane.
Kondo teaches an electrolyte for a non-aqueous electrolyte battery comprising at least one compound selected from the group consisting of lithium difluoro(bis(oxalato))phosphate. See Abstract. Kondo found that by adding a siloxane compound to an electrolyte solution, the free acid concentration can be reduced. This can suppress the initial decrease in the electric capacity. This results in an improvement in storage stability, cycle characteristics, internal resistance, and others. Many examples of siloxane containing compounds are presented and is not limited in use. Hexamethyldisiloxane is the first example shown for siloxanes. In Example 1-1, the free acid content in the solution was 2 ppm when measured 2 hours after preparation. Lithium hexafluorophosphate is a particularly preferred solute. Concentrations of solute are not limited and can vary from 0.5 mol/L to 2.5 mol/L.
Kondo does not teach crystallization.
Morinaka teaches a method of purifying a complex salt, such as lithium difluorobis(oxalato)phosphate by crystallization with a non-aqueous solvent. See par. 8. The non-aqueous solvent can be n-hexane, 1,2-dichloroethane, or toluene among a limited list. See par. 26. Table 1 provides Examples 7 and 8 in which the claimed lithium difluorobis(oxalato)phosphate in crystallized in a non-aqueous solvent. The purified crystal includes a low concentration of chloride (i.e., halogen) and a low free acid concentration. See par. 36 and Table 1. Examples includes solid that is washed, filtered and dried under reduced pressure with a purity of 99%. See par. 45. Additionally, the purification process shown in Table 7 provides a substantial decrease in impurities. As known in the art and described by Morinaka, when a high purity is required a repurification can often be performed.
With regard to claim 3, Pure materials are novel vis-à-vis less pure or impure materials because there is a difference between pure and impure materials. Therefore, the issue is whether claims to a pure material are nonobvious over the prior art. In re Bergstrom, 427 F.2d 1394, 166 USPQ 256 (CCPA 1970). Purer forms of known products may be patentable, but the mere purity of a product, by itself, does not render the product nonobvious. See M.P.E.P. § 2144.04.
With regard to claim 12, the prior art does not appear to state a level of metal ion impurity. However, the reactants as well as high level of impurity, low moisture content, and low halogen concentrations are taught by the prior art. Additionally, using a claimed siloxane is also motivated. As such, the burden has shifted to Applicant to explain how the claimed level of impurity is not present in the cited prior art and how such distinction is not optimizable in view of purification and crystallization procedures being known and employed. Even further, if it is not routine knowledge in the field and state of the art to purify the known agent to a metal ion purity of 0 to 10 ppm as claimed, the instant Specification would be considered by the Examiner to be insufficient in teaching a POSA how to arrive at the same. The Specification provides Table 1 showing metal ion impurity content in Examples 1-14 ranging from 6.5 to 10.8. There is no method shown that yield a level below 6.5 ppm. As such, the crystallization and recrystallization known purification techniques as well as those additional processes described by prior art are though to yield such low levels of impurities absent evidence to the contrary. To overcome this rejection Applicant should (1) explain how the prior art does not yield this limitation necessarily and (2) explain that the state of the art does not also render this optimizable while at the same time explaining how the Specification teaches a POSA how to do so.
It would have been prima facie to a person having ordinary skill in the art prior to the filing of the instant application to combine the teachings of the cited prior art to arrive at the claimed methods and products. One would be motivated to do so because Feng teaches a method for preparing a solution comprising lithium difluorobis oxalate phosphate by reacting oxalyl chloride in a non-aqueous solvent and further mixing lithium hexafluorophosphate to obtain a lithium difluorobis oxalate phosphate solution. Further, the claimed non-aqueous solvent are taught. The non-aqueous solvent is also taught to have moisture/water content of less than 10 ppm and a chloride ion content measured to be less than 5 ppm. While Feng does not teach incorporating a siloxane, Kondo also teaches producing lithium difluoro(bis(oxalato))phosphate components and provides specific advantages for incorporating a variety of siloxanes into an electrolyte solution wherein advantages include: a low free acid content and an enhanced ability to suppress an initial decrease in electric capacity. Claimed siloxanes are provided in examples. Even further, Morinaka provides methods for purification and crystallization of lithium difluorobis(oxalate)phosphate in solvents that include those claimed “poor solvents” and the purer product is taught to have an advantageously low halide content and low acid content. The ratios and concentrations of component are routinely optimizable result-effective variables. Further, there is no reason to believe that the steps taught by the prior art which include using the same reactants, including oxalyl chloride and lithium hexafluorophosphate with a specific motivation to use a claimed siloxane yielding low acid and halogen concentrations would not also include low levels of other impurities in view of the teachings to undertake crystallization and even recrystallization process to yield highly pure product.
Claims 10-15 are rejected under 35 U.S.C. 103 as being unpatentable over Zhao et al., (CN110845539A) (cited in ISR), in view of Morinaka et al., (EP2857406 B1).
Zhao teaches a battery-grade lithium difluorobis (oxalato) phosphate solid. The chloride ion content is 10 ppm or less and the moisture and oxygen content is less than 1 ppm. In Example 2, the chloride ion content was 3.5 ppm. The solid component is part of a electrolyte component and battery additive. These electrolytes are often components in lithium-ion batteries.
Morinaka further teaches a method of purifying a complex salt, such as lithium difluorobis(oxalato)phosphate by crystallization with a non-aqueous solvent. See par. 8. The non-aqueous solvent can be n-hexane, 1,2-dichloroethane, or toluene among a limited list. See par. 26. Table 1 provides Examples 7 and 8 in which the claimed lithium difluorobis(oxalato)phosphate in crystallized in a non-aqueous solvent. The purified crystal includes a low concentration of chloride (i.e., halogen) and a low free acid concentration. See par. 36 and Table 1. Examples includes solid that is washed, filtered and dried under reduced pressure with a purity of at least 99%. See par. 45. Additionally, the purification process shown in Table 7 provides a substantial decrease in all impurities. As known in the art and described by Morinaka, when a high purity is required a repurification can often be performed. While this will reduce product in some instances, it remains known to arrive at a purer product.
“[E]ven though product-by-process claims are limited by and defined by the process, determination of patentability is based on the product itself. The patentability of a product does not depend on its method of production. If the product in the product-by-process claim is the same as or obvious from a product of the prior art, the claim is unpatentable even though the prior product was made by a different process.” In re Thorpe, 777 F.2d 695, 698, 227 USPQ 964, 966 (Fed. Cir. 1985) (citations omitted). See M.P.E.P. § 2113.
Moreover, pure materials are novel vis-à-vis less pure or impure materials because there is a difference between pure and impure materials. Therefore, the issue is whether claims to a pure material are nonobvious over the prior art. In re Bergstrom, 427 F.2d 1394, 166 USPQ 256 (CCPA 1970). Purer forms of known products may be patentable, but the mere purity of a product, by itself, does not render the product nonobvious. See M.P.E.P. § 2144.04.
With regard to claim 12, the prior art does not appear to state a level of metal ion impurity. However, the reactants as well as high level of impurity, low moisture content, and low halogen concentrations are taught by the prior art. Additionally, using a claimed siloxane is also motivated. As such, the burden has shifted to Applicant to explain how the claimed level of impurity is not present in the cited prior art and how such distinction is not optimizable in view of purification and crystallization procedures being known and employed. Even further, if it is not routine knowledge in the field and state of the art to purify the known agent to a metal ion purity of 0 to 10 ppm as claimed, the instant Specification would be considered by the Examiner to be insufficient in teaching a POSA how to arrive at the same. The Specification provides Table 1 showing metal ion impurity content in Examples 1-14 ranging from 6.5 to 10.8. There is no method shown that yield a level below 6.5 ppm. As such, the crystallization and recrystallization known purification techniques as well as those additional processes described by prior art are though to yield such low levels of impurities absent evidence to the contrary. To overcome this rejection Applicant should (1) explain how the prior art does not yield this limitation necessarily and (2) explain that the state of the art does not also render this optimizable while at the same time explaining how the Specification teaches a POSA how to do so.
It would have been prima facie to a person having ordinary skill in the art prior to the filing of the instant application to combine the teachings of the cited prior art to arrive at the claimed products. One would be motivated to do so because Zhao teaches a battery-grade lithium difluorobis (oxalato) phosphate solid. The chloride ion content is 10 ppm or less and the moisture and oxygen content is less than 1 ppm. In Example 2, the chloride ion content was 3.5 ppm. The solid component is part of a electrolyte component and battery additive. These electrolytes are often components in lithium-ion batteries. While Zhao does not teach the content of a metal impurity ion, the methods described by Zhao would appear to yield substantially low impurities even prior to specific purification procedures. Even further, Morinaka provides methods for purification and crystallization of lithium difluorobis(oxalate)phosphate in solvents that include those claimed “poor solvents” and the crystallization/purification process yields an advantageously low halide content and low acid content. The ratios and concentrations of component are routinely optimizable result-effective variables.
As such, no claim is allowed.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to JARED D BARSKY whose telephone number is (571)272-2795. The examiner can normally be reached on 9-5 M-F.
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/JARED BARSKY/Primary Examiner, Art Unit 1628