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 .
DETAILED ACTION
This Office action regarding Application No. 17/777,360 to Ge et al., assigned to Albemarle Corporation, Charlotte, U.S.A., filed 05/17/2022 and published as U.S. PG Publication 20220416300 on 12/29/2022 is in response to applicant’s arguments/remarks and claims amendment filed 12/10/2025.
Status of the Claims
In the response filed 12/10/2025 the status of the claims stand as follows:
Currently amended 1-2, 4-6, 9-10, 12, 14-18, 20-23, 25-26,
Canceled (previously) 3, 7-8, 11, 13, 19, 24, 28-32, 35
Previously presented 27
Withdrawn 33-34, 37
Claims 1-2, 4-6, 9-10, 12, 14-18, 20-23, 25-27, 33-34, 37 are currently pending in this application. Claims 33-34, 37 have been withdrawn from consideration for being non-elected claims. All elected claims 1-2,4-6,9-10, 12-18, 20-23, 25-27 are under full consideration.
Withdrawal of Claims Objection
The amendment of claims 2, 4-6, 9-10, 12, 14-18, 20-23, 25-26 now reciting “a nonaqueous electrolyte solution” instead of the previously recited “a solution” has overcome the previously presented objection. Therefore, the objection is now withdrawn.
Withdrawal of Claims Rejections – 35 USC § 112
The amendments of claims 2, 6, 10, 14, , 15,16, 16, 22, 23 by deleting the word “about” regarding the number of carbon atoms, bromine atoms (in claims 2, 14, 15), temperature range (in claim 10), wt% (in claims 2, 6, 16, 18,22, 23) have overcome the previously presented rejection. Therefore, the rejection have been withdrawn.
Claim Rejection -35 USC § 103
The text of those sections of Title 35 U.S. Code not included in this section can be found in the prior Office Action.
Claims 1-2, 4-6, 9, 12, 14, 16-18, 20-23, 25-27 are rejected under 35 U.S.C. 103 as being unpatentable over Ihara et al. (U.S. PG Publication 2008/0085454)
This rejection was presented in the previous non-final Office action, but it is modified here as necessary to address the amendment of the claim.
Regarding claim 1 and 27 Ihara discloses a battery having a cathode and an anode and an electrolyte (Ihara paragraph 0008, 0019), the liquid electrolyte include an organic solvent and an electrolyte salt dissolved in the solvent (Ihara paragraph 0019) forming an nonaqueous electrolyte solution, the solvent is equivalent to the liquid electrolyte medium, and the salt can be lithium-containing salt (Ihara paragraph 0033); thus, the battery is a nonaqueous lithium battery as recited in claim 27, and the electrolyte further comprise a cyclic carbonate of the formula 11 (Ihara claim 15) wherein R1, R2, R3, R4 represent a methyl group and ethyl group or groups in which a part of hydrogen thereof is substituted by a halogen group and at least one group among them has a halogen group (Ihara paragraph 0025), and such a compound is representative of brominated cyclic carbonate having a carbonate ring, and in which the carbon-carbon bond is saturated, where there are one or more hydrocarbyl (i.e. hydrocarbon) groups R1, R2, R3, R4 bound to the ring, and wherein all the halogen atoms, which can be a bromine atoms, are in the one or more hydrocarbyl (i.e. hydrocarbon) groups R1, R2, R3, R4. Such a compound is also equivalent to the flame retardant since it has the same chemical composition as the claimed compound.
The compound 11 (Ihara paragraph 0025) is representative of a large class of brominated cyclic carbonate as claimed. But Ihara does not explicitly disclose that the compound is not 4-bromometyl ethylene carbonate. However, it would have been obvious to a person of ordinary skill to have selected any other compound from among the representative compounds and to have excluded 4-bromethyl ethylene carbonate. Such a choice constitute choosing from among a finite number of identified, predictable solutions, with a reasonable expectation of success (MPEP 2143 I E).
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Ihara Formula 11 [0025]
Regarding claim 2 Ihara discloses the above presented brominated cyclic carbonate compound (Ihara paragraph 0025), and can have a bromine content within the wt% of the total weight of the oxygen-containing brominated flame retardant. This wt% value is included in the claimed rage of about 35 wt% or more relative to total weight of the compound.
Regarding claim 4 Ihara discloses the cyclic carbonate of formula 11 (also Formula 5 in claim 5) wherein, R1, R2, R3, R4 represent a hydrogen group, a halogen group, or a methyl group and an ethyl group, or groups in which a part of hydrogen thereof is substituted by a halogen group (Ihara paragraph 0025), wherein the halogen can be more than one bromine atom, and the methyl and ethyl groups are hydrocarbyl groups, and the bromine groups can be in different hydrocarbyl groups. Ihara's disclosure does not put any restriction on the substitution of the hydrogen by the halogen, which can be bromine substitution of any or all of R1 to R4 groups or substituting any of the H in the R1 to R4 hydrocarbyl groups, and the hydrocarbyl group can be an ethyl group. Therefore, the bromine can be in one or more of the ethyl groups, equivalent to the hydrocarbyl groups. Such compounds can also have the bromine wt% in the claimed range.
Regarding claim 4 Ihara discloses the cyclic carbonate of formula 11 (also Formula 5 in claim 5) wherein, R1, R2, R3, and R4 represent a hydrogen group, a halogen group, or a methyl group and an ethyl group, or groups in which a part of hydrogen thereof is substituted by a halogen group (Ihara paragraph 0025), wherein the halogen can be more than one bromine atom, and the methyl and ethyl groups are hydrocarbyl groups, and the bromine groups can be in different hydrocarbyl groups. Ihara's disclosure does not put any restriction on the substitution of the hydrogen by the halogen, which can be bromine substitution of any or all of R1 to R4 or substituting any of the H in the R1 to R4 hydrocarbyl groups. Therefore, the bromine can be in one or more of the methyl or ethyl groups, equivalent to the hydrocarbyl groups, or the bromine atoms can bound to carbon atoms of the carbonate ring as claimed.
Regarding claim 5 Ihara discloses the cyclic carbonate of formula 11 (also Formula 5 in claim 5 of Ihara) wherein R1, R2, R3 and R4 represent a hydrogen group, a halogen group or a methyl group or an ethyl group, equivalent to the hydrocarbyl groups, bound to the carbonate ring, or groups in which a part of hydrogen thereof is substituted by a halogen group (Ihara paragraph 0025). Therefore, the halogen can be one or more than one bromine atoms, and the methyl group and the ethyl group, equivalent to the hydrocarbyl groups, can be bonded to the carbonate ring and the bromine atoms can be bonded to different hydrocarbyl groups as claimed.
Regarding claim 6 the compound represented by formula 11 and disclosed by Ihara (Ihara paragraph 0025) has cyclic carbonate structure that is brominated and has a five-membered ring and can have three carbon atoms in the ring and other four carbon atoms in two ethyl groups having seven carbon atoms included in the claimed range of carbon atoms, and can also have one to five bromine atoms in a wt% content included in the claimed range (Ihara paragraph 0025).
Regarding claim 9 Ihara discloses the cyclic carbonate of formula 11 (also Formula 5 in claim 5 of Ihara) wherein R1, R2, R3 and R4 represent a hydrogen group, a halogen group or a methyl group or an ethyl group, or groups in which a part of hydrogen thereof is substituted by a halogen group (Ihara paragraph 0025), where the halogen can be one or more than one bromine atom (Ihara paragraph 0025). Ihara disclosure does not put any restriction on the substitution of the hydrogen by the halogen, which can be bromine substitution of any or all of R1 to R4 hydrocarbyl groups. Therefore, when one of R1, R2, R3 or R4 is a bromo-ethyl group, and the rest are hydrogen atoms is the same as the claimed compound 4-(2-bromoethenyl)-1,3-dioxolan-2-one.
Regarding claim 12 the cyclic carbonate compound represented by formula 5 wherein R1, R2, R3, R4 can be substituted by a halogen (such as a bromine) can be found in the range 0.01% by weight to 50% by weight of the solution (Ihara paragraph 0022, 0023). This range over laps with the claimed range of 10 wt% or more. The solvent can be ethylene carbonate (Ihara 0029), and lithium salt can be lithium di(fluoro) (oxalato borate (Ihara formula 22, paragraph 0033).
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Ihara Formula 22
Regarding claim 14, 17 Ihara discloses the electrolyte comprises at least one lithium salt (Ihara claim 9) and one or more than one or two or more salt may be mixed for use (Ihara paragraph 0031), equivalent to at least one electrochemical additive is another lithium-containing salt.
Regarding claim 16, 18 Ihara discloses in specific example the use of two lithium containing salts (Ihara Table 3), present in amounts 0.9 mol/kg and 0.1 mol/kg of the electrolyte (Ihara Table 3) the second lithium-containing salt is equivalent to the claimed electrochemical additive that is another lithium-containing salt. The second or the-another lithium-containing compound is found in about 10% wt of the first lithium-containing compound (Ihara Table 3), meaning it is found in even much reduced minor amount in the overall weight of the nonaqueous electrolyte solution.
Ihara is silent about such a minor amount is in the claimed range of about 0.4 wt% to about 5 wt% of claim 16 or is about 1 wt% to about 4 wt% of claim 18 relative to the total weight of the nonaqueous electrolyte. However, it would have been obvious to a person of ordinary skill to have optimized through routine experimentation the range of the additive other lithium-containing compound to obtain a high temperature storage stability of the battery (Ihara paragraph 0108). According to the MPEP, "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). (MPEP 2144.05 II A)
Regarding claim 20 Ihara discloses the electrolyte comprises at least one lithium salt and one or more than one or two or more salt may be mixed for use (Ihara paragraph 0031) (Ihara claim 9, paragraph 0031), and when one lithium salt and a second lithium salt equivalent to an additive lithium-containing salt is used, is considered equivalent to the claimed limitation, wherein each of the electrochemical additive is not used with another electrochemical additive.
Regarding claim 21 Ihara discloses the electrolyte comprises at least one lithium salt (Ihara claim 9) and one or more than one or two or more salt may be mixed for use (Ihara paragraph 0031), equivalent to at least one electrochemical additive is another lithium-containing salt. Ihara discloses the other lithium salt can be lithium di(fluoro) (oxalato borate (Ihara formula 22, paragraph 0033).
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Ihara Formula 22
Regarding claim 22, 23 Ihara is silent about the content of the lithium di(fluoro) (oxalato) borate electrochemical additive is in any of the ranges claimed. Ihara discloses in specific example the use of two lithium containing salts (Ihara Table 3), present in amounts 0.9 mol/kg and 0.1 mol/kg of the electrolyte (Ihara Table 3) the second lithium-containing salt is equivalent to the claimed electrochemical additive that is another lithium-containing salt. The second or the-another lithium-containing compound is found in about 10% wt of the first lithium-containing compound (Ihara Table 3), meaning it is found in even much reduced minor amount in the overall weight of the nonaqueous electrolyte solution.
But Ihara is silent about such a minor amount is in the claimed range of about 0.4 wt% to about 10 wt% or about 1 wt% to 4 wt% of claim 22 or is about 1 wt% to about 4 wt% of claim 23 relative to the total weight of the nonaqueous electrolyte. However, it would have been obvious to a person of ordinary skill to have optimized through routine experimentation the range of the additive other lithium-containing compound to obtain a high temperature storage stability of the battery (Ihara paragraph 0108). According to the MPEP, "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, 220 454, 456, 105 USPQ 233, 235 (CCPA 1955). (MPEP 2144.05 II A).
Regarding claim 25 Ihara discloses the cyclic carbonate of formula 11 (also Formula 5 in claim 5) wherein, R1, R2, R3, and R4 represent a hydrogen group, a halogen group, or a methyl group and an ethyl group, or groups in which a part of hydrogen thereof is substituted by a halogen group (Ihara paragraph 0025), wherein the halogen can be more than one bromine atom, and the methyl and ethyl groups are hydrocarbyl groups, and the bromine groups can be in different hydrocarbyl groups. Ihara's disclosure does not put any restriction on the substitution of the hydrogen by the halogen, which can be bromine substitution of any of R1 to R4 and so represented by the compound of claim 25.
Regarding claim 26 Ihara discloses the electrolyte comprise at least one lithium salt and one or more than one or two or more salt may be mixed for use (Ihara paragraph 0031) (Ihara claim 9, paragraph 0031), and when one lithium salt and a second lithium salt equivalent to an additive lithium-containing salt is used, is considered equivalent to the claimed limitation, wherein each of the electrochemical additive is not used with another electrochemical additive.
Claim 10 is rejected under 35 U.S.C. 103 as being unpatentable over Ihara et al. (U.S. PG Publication 2008/0085454) as evidenced by Yamaguchi (U.S. PG Publication 2009/0123849)
The discussion of Ihara as applied to claim 1 is fully incorporated here and is relied upon for the limitation of the claim in this section.
Regarding claim 10 Ihara discloses the electrolyte comprise a cyclic carbonate of the formula 11 (Ihara paragraph 0025) wherein R1, R2, R3 and R4 can represent alkyl groups substituted by halogen atoms (Ihara paragraph 0025) such as bromine. But Ihara is silent about the boiling points of the disclose brominated cyclic compounds such as those represented by compound formula 11. Yamaguchi discloses examples of high boiling solvent include cyclic carbonates such as ethylene carbonate having boiling points higher than 150 °C (Yamaguchi paragraph 0033, 0034), and as evidenced by Yamaguchi the brominated cyclic carbonates disclosed by Ihara and equivalent to the claimed compounds will have a high boiling point, at least greater than 150 °C, which overlaps with claimed range of 75 °C to 450 °C.
Claim 15 is rejected under 35 U.S.C. 103 as being unpatentable over Ihara et al. (U.S. PG Publication 2008/0085454) in view of Hancock et al. (U.S. PG Publication 2020/0335825)
The discussion of Ihara as applied to claim 1 and 14 is fully incorporated here and is relied upon for the limitation of the claim in this section.
Regarding claim 15 Ihara discloses the electrolyte further comprises at least one other lithium salt (Ihara paragraph 0031), equivalent to the electrochemical additive. But Ihara is silent that the electrochemical additive is cyclic sultone containing three to about four carbon atoms. Hancock discloses a non-aqueous electrolyte composition (Hancock paragraph 0008,0024) and the electrolyte solution further comprise a cyclic carbonate (Hancock paragraph 0139 Formula VIII). In some embodiment the electrolyte composition further comprises a cyclic sultone (Hancock paragraph 0131, 0133, 0134), and suitable sultones include those represented by the following formula (Hancock paragraph 0133, 0134):
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Hancock, cyclic sultone , paragraph[0133]
Where A in the structural formula above can be hydrogen; thus, the cyclic sultone has three carbon atoms as claimed. Hancock also discloses 1,3-propane sultone among other compounds that are suitable gas-reduction additives (Hancock paragraph 0143), and high temperature storage (Hancock paragraph 0007). Therefore, it would have been obvious to a person of ordinary skill in the art to have used cyclic sultone additive in the electrolyte of the battery Ihara as disclosed by Hancock as a gas-reduction additive (Hancock paragraph 0143) and high temperature storage (Hancock paragraph 0007). According to the MPEP such a modification is considered the use of known technique to improve similar devices (methods, or products) in the same way (MPEP 2143 I C). Choosing the 1,3-propane sultone from among other compounds would have been obvious to try since it constitutes choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success (MPEP 2143 I E).
Response to Argument
The examiner notes that the amendment to the claims overcomes the claims objection presented in the previous non-final Office action. Consequently, as presented above in this Office action the objection to claims has been withdrawn.
The examiner also notes the amendment to the claims also overcomes the 112(b) rejection of the claims for reciting the relative term “about”. The word “about” recited in relation to the number of carbon atom and bromine atoms, temperature range and wt% have been deleted from all claims. Therefore, the rejection has been withdrawn.
Applicant traverses the rejection of the claims under 103 over the reference of Ihara (U.S. PG {Publication 2008/0085454). Applicant refers to Formula 1 and Formula 2 of the Ihara and argues that the compounds of Formula 1 and 2 are not cyclic carbonates. Examiner notes that Formula 1 and 2 are embodiment of the claimed compound, but the rejection relies upon the disclosure of Formula 11, which is a cyclic carbonate having hydrocarbyl groups, i.e. hydrocarbon groups, at carbon 4 and 5, and have substituents groups R1, R2, R3, R4 which can be methyl and ethyl hydrocarbyl groups i.e. hydrocarbon groups, and which a part of is substituted by halogen atoms, the halogen atoms being F, Cl, Br, I, At. Thus, the compounds represented by Formula 11 include the brominated cyclic carbonate compound.
Applicant argues that Ihara des not describe the disclosed compound as flame retardant. Examiner notes that since the disclosed compound of Ihara are the same as the claimed compounds they will also have the same properties. Therefore, if the prior art teaches the identical chemical structure, the properties applicant discloses and/or claims are necessarily present." (In re Spada, 911 F.2d 705, 709, 15 USPQ2d 1655, 1658, Fed. Cir. 1990) See MPEP 2112.01 II
Applicant argues that the preferred halogenated cyclic compounds of Ihara are fluorinated carbonates. Examiner notes that Ihara discloses the side hydrocarbyl groups in which a part of the hydrogen thereof is substituted by a halogen group. And since bromine is a halogen, it is included in the disclosure of Ihara. According to the MPEP, “A reference may be relied upon for all that it would have reasonably suggested to one having ordinary skill the art, including nonpreferred embodiments. Merck & Co. v. Biocraft Laboratories, 874 F.2d 804, 10 USPQ2d 1843 (Fed. Cir.), cert. denied, 493 U.S. 975 (1989).” (See MPEP 2123 I).
Regarding the rejection of claim 10 applicant while noting that the reference of Yamaguchi (U.S. PG Publication 2009/0123849) is being cited as an evidence argues that it does not cure the deficiency of Ihara, and notes that Ihara as evidenced by Yamaguchi does not teach or suggest each and every element of claim 1. Examiner refers to the discussion above regarding the disclosure of the reference of Ihara and as presented in the previous Office action and in this Office action the claimed invention is obvious over the disclosure of Ihara. Yamaguchi is hence relied upon as an evidence reference with regard to the limitation of claim 10 only.
Regarding the rejection of claim 15 is relied upon for its disclosure of the additive cyclic sultone containing three to about four carbon atoms. And the combined teaching of Ihara and Hancock meets the limitation of claim 15.
As is presented above in this Office action, the previous rejection has been modified as necessary to address the amendment of the claims, though the same prior art references are applied. The teaching of Ihara renders the limitation of the claims obvious. Further for claims 10 and 15 secondary supporting references are used, and the combined teaching of Ihara and the secondary references meet the limitation of claim 10 and 15. This Office action is made final.
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.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to OMAR M KEKIA whose telephone number is (571)270-5918. The examiner can normally be reached 9:00am-5:00 pm,.
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/OMAR M KEKIA/Examiner, Art Unit 1722
/NIKI BAKHTIARI/Supervisory Patent Examiner, Art Unit 1722