Detailed Action
This is a Non-Final Office action based on application 18/102,254 filed on January 27, 2023. The application is a 111(a) of with priority to US provisional application 63/303,678 filed January 27, 2022.
Claims 1-25 are pending and have been fully considered.
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 .
Information Disclosure Statement
The specification at pg 1 ln 7 and pg 2 ln 21-23, attempts to cite references which are not listed in the information disclosure statement. The listing of references in the specification is not a proper information disclosure statement. 37 CFR 1.98(b) requires a list of all patents, publications, or other information submitted for consideration by the Office, and MPEP § 609.04(a) states, "the list may not be incorporated into the specification but must be submitted in a separate paper." Therefore, unless the references have been cited by the examiner on form PTO-892, they have not been considered.
Drawings
The following is a quotation from 37 C.F.R. 1.84:
(l) Character of lines, numbers, and letters. All drawings must be made by a process which will give them satisfactory reproduction characteristics. Every line, number, and letter must be durable, clean, black (except for color drawings), sufficiently dense and dark, and uniformly thick and well-defined. The weight of all lines and letters must be heavy enough to permit adequate reproduction.
The drawings of figures 3-4 and 6 are objected to because letters, numbers, and graph axes are rendered in shades of gray, rather than in clean black ink sufficiently dense and dark to permit accurate reproduction. Applicant is advised to submit corrected drawings that show the text and graph information in clear black and white.
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. The figure or figure number of an amended drawing should not be labeled as “amended.” If a drawing figure is to be canceled, the appropriate figure must be removed from the replacement sheet, and where necessary, the remaining figures must be renumbered and appropriate changes made to the brief description of the several views of the drawings for consistency. Additional replacement sheets may be necessary to show the renumbering of the remaining figures. 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.
Claim Objections
Claim 16 is objected to because of minor informalities. Claim 16 recites:
The method of claim 15, wherein ion exchange resin characterized by a ratio of quaternary ammoniums to tertiary amines of less than 5:100.
However, the claim does not contain a verb. Also, the noun “ion exchange resin” lacks an article. Examiner suggests the claim should be corrected to read:
The method of claim 15, wherein the ion exchange resin is characterized by a ratio of quaternary ammoniums to tertiary amines of less than 5:100.
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.
Claim 25 is 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 25 recites the limitation "the anode" in step (c), at line 8. There is insufficient antecedent basis for this limitation in the claim.
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.
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.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claims 1-4, 6-7, and 14-21 are rejected under 35 U.S.C. 103 as being unpatentable over “Shown” (US 2016/0199829 A1 to Shown et al), in view of “Takahashi” (US 2020/0115401 A1 to Takahashi et al).
Regarding claim 1, Shown discloses using an ion exchange resin for absorbing ion species from an organic solvent (para [0044], “Partially spent ion-exchange resin is obtained from a source where highly acidic crude oil is treated with ion-exchange resin for neutralization and desalting”; para [0060]-[0065]), and a method for regenerating said ion exchange resin (para [0042], “a method of treatment of at least partially spent ion-exchange resin to obtain regenerated ion-exchange resin”). Shown’s method comprises:
- providing an ion exchange resin comprising an absorbed ion species and a first organic solvent (para [0045], “the obtained spent ion-exchange resin is contacted with at least one non-acidic crude oil condensate, to obtain partially cleansed ion-exchange resin, followed by at least one polar organic solvent to obtain heavy hydrocarbon free ion-exchange resin. The non-acidic lighter crude oil condensate and the polar organic solvent do not interact with acids and salts adhered on the ion-exchange resin. However, they selectively remove the adhered compounds such as asphaltenes”; i.e., the ion exchange resin, after this step, comprises an organic solvent and also still has ionic species absorbed to it; para [0075]),
- adding at least one solution comprising water to the ion exchange resin comprising adsorbed ionic species and organic solvent to produce a regenerated ion exchange resin (para [0051], “In the next step, the heavy hydrocarbon free ion-exchange resin is treated with at least one alkali or alkaline earth metal hydroxide solution to obtain activated ion-exchange resin”; para [0077], “5 wt % 5 BV aqueous caustic solution was passed through the packed resin ... the resin bed was washed with demineralized water”),
- placing the regenerated ion exchange membrane into service by wetting it with a process solution comprising a second organic solvent (para [0078], “The resin obtained was tested for its recyclability by subjecting it iteratively to the similar process as mentioned in Experiment 1 step C. It was found that resin could be recycled for 34 times”; para [0060]-[0065], Experiment 1 step C involves passing an acidic crude oil through the ion exchange resin to absorb acids and salts from the oil onto the resin).
Shown does not disclose removing the water to produce a dried ion exchange resin prior to wetting the ion exchange resin with the second organic solvent.
Takahashi is similarly directed to absorbing ionic impurities from nonaqueous media by contacting the media with ion exchange resin, and particularly towards purification of nonaqueous electrolyte solutions for battery applications (para [0028]-[0029], “producing a nonaqueous electrolyte solution including a phosphoryl imide salt having a predetermined structure through the cation exchange”).
The nonaqueous solutions that Takahashi is purifying with ion exchange resin contain a water-sensitive solute (para [0111]-[0118]), and Takahashi specifies that these solutions should be kept relatively free of water (para [0119], the water content of that solution is preferably in a range of from 1 to 500 ppm).
Takahashi teaches that a resin that is suitable for the purpose of purifying their dry nonaqueous solution without introducing additional water is one that is prepared for use by ion exchanging the resin with an aqueous alkali hydroxide regenerant solution, then removing water from the resin by application of heat and vacuum in order to produce a dried resin (para [0280], [0297]).
It would have been obvious to a person having ordinary skill in the art before the effective filing date of the claimed invention to modify the method of modified Shown by adding a step, after regenerating the resin in aqueous caustic and before placing the resin in contact with the second organic solvent, of drying the resin to remove water from it and produce a dried resin, to prevent the resin from carrying excess water over into the second solvent, as taught in Takahashi (para [0280], [0297]). Such a modification would broaden the utility of Shown’s resin regeneration method by making it suitable for ion exchange treatment of water-sensitive nonaqueous solution such as those used by Takahashi. Furthermore, the claimed limitations are obvious because all the claimed elements were known in the prior art and one skilled in the art could have combined the elements as claimed by known methods with no change in their respective functions, and the combination yielded nothing more than predictable results [MPEP 2143(A)].
Regarding claim 2, Shown and Takahashi render the method of claim 1 obvious, and Takahashi teaches that the process solution that the ion exchange resin is employed to treat (i.e. the second solvent) should have a water content in a range of 0.3 wt% or less, preferably 0.05 wt% or less. The instant specification at pg 5 states that anhydrous organic solvent can have a water content in the range of less than 1 vol% or less, therefore Takahashi’s disclosure of solvent comprising 0.3 wt% or less of water reads on the claim limitation to anhydrous solvent.
Regarding claim 3, Shown and Takahashi render obvious the method of claim 2 and Takahashi further teaches the second organic solvent contains from 0.3 to 0.0001 wt% water (para [0118]-[0123]), which falls within the claimed range of less than 1 vol % water.
Regarding claim 4, Shown and Takahashi render the method of claim 1 obvious, and Shown teaches the first and second organic solvents are the same (para [0060]-[0065], [0078], the solution which is purified by ion exchange (i.e. the solution comprising the second solvent) is acidic crude oil; para [0029]-[0030], [0045], [0075], the solution with which the resin is treated in the first stage of regeneration (i.e. comprising the first organic solvent) is non-acidic crude oil condensates e.g. kerosene).
Regarding claim 6, Shown and Takahashi render the method of claim 1 obvious. Shown and Takahashi are silent with respect to the water content of the dried ion exchange resin. However, since Takahashi’s process step of removing water from ion exchange resin to produce dried ion exchange membrane is identical to the claimed process step of producing dried ion exchange membrane, it is presumed that Takahashi’s dried ion exchange resin has the claimed property of a water content of less than 5 wt% water. When claimed and prior art products are produced by identical or substantially identical processes, a prima facie case of either anticipation or obviousness has been established. In re Best, 562 F.2d 1252, 1255, 195 USPQ 430, 433 (CCPA 1977).
Regarding claim 7, Shown and Takahashi render the method of claim 1 obvious, and Shown teaches that the absorbed ionic species is an acid (para [0003]-[0009], [0044], [0051], [0057], the resin absorbs acids and salts from acidic crude oil, particularly organic carboxylates, and more particularly naphthenic acids).
Regarding claim 14, Shown and Takahashi render the method of claim 1 obvious. Furthermore Shown teaches that the solution comprising water is flowed through the ion exchange resin bed (para [0077]), which necessarily implies that the ion exchange resin bed is porous.
Regarding claim 15, Shown and Takahashi render the method of claim 1 obvious, and Shown teaches the ion exchange resin may comprise one or more of tertiary amine functional groups and quaternary ammonium functional groups (para [0033], [0046], claim 7). It would have been obvious to a person having ordinary skill in the art before the effective filing date of the claimed invention to select a suitable ion exchange resin comprising tertiary amine functional groups, based on Shown’s teaching that a resin comprising tertiary amine functional groups is suitable for use in the invention. The selection of a known material, which is based upon the prior art’s disclosure that it is suitable for the intended use, is within the ambit of one of ordinary skill in the art [MPEP § 2144.07].
Regarding claims 16-17, Shown and Takahashi render the method of claim 15 obvious, with Shown teaching that the ion exchange resin may comprise tertiary amine functional groups either alone or in combination with quaternary ammonium functional groups (para [0033], [0046], claim 7). It would have been obvious to a person having ordinary skill in the art before the effective filing date of the claimed invention to select a suitable ion exchange resin comprising exclusively tertiary amine functional groups, based on Shown’s teaching that a resin comprising tertiary amine functional groups is suitable for use in the invention. The selection of a known material, which is based upon the prior art’s disclosure that it is suitable for the intended use, is within the ambit of one of ordinary skill in the art [MPEP § 2144.07].
Regarding claim 18, Shown and Takahashi render the method of claim 1 obvious. Shown teaches that the solution comprising water has the effect of regenerating the ion exchange resin, (para [0051], “In the next step, the heavy hydrocarbon free ion-exchange resin is treated with at least one alkali or alkaline earth metal hydroxide solution to obtain activated ion-exchange resin”; para [0077], “5 wt % 5 BV aqueous caustic solution was passed through the packed resin ... During passage of caustic solution through the resin, the resin gets activated as the RCOO− ion adhered on the resin is replaced by active OH− ion”), from which it follows that the solution comprising water is a regenerant.
Regarding claim 19, Shown and Takahashi render the method of claim 1 obvious, and Shown teaches the solution comprising water comprises alkali or alkaline hydroxide (para [0051], “alkali or alkaline earth metal hydroxide solution”; para [0077], “aqueous caustic solution was passed through the packed resin”), and that a suitable alkali or alkaline hydroxide for use in the invention is NaOH (para [0040], [0051]). It would have been obvious to a person having ordinary skill in the art before the effective filing date of the claimed invention to select, as the alkali or alkaline hydroxide in Shown’s method, NaOH, based on Shown’s teaching that NaOH is a suitable alkali hydroxide for use in their method. The selection of a known material, which is based on its suitability for the intended use, is within the ambit of one of ordinary skill in the art [MPEP § 2144.07].
Regarding claim 20, Shown and Takahashi render the method of claim 1 obvious, and Shown teaches the adsorbed ion species is substantially removed from the ion exchange resin (para [0051], “carboxylate anion (RCOO−) is freed after exchange with hydroxyl anion (OH−) of alkali or alkaline earth metal hydroxide solution which is then removed by iterative washing with a washing media to obtain regenerated ion-exchange resin”).
Regarding claim 21, Shown and Takahashi render the method of claim 1 obvious, and Takahashi teaches the step of removing water is performed under vacuum (para [0280], “moisture was removed by vacuum drying”).
Claim 5 is rejected under 35 U.S.C. 103 as being unpatentable over Shown and Takahashi as applied to claim 1 above, and further in view of “Taniguchi” (US 2016/0355491 A1 to Taniguchi et al).
Regarding claim 5, Shown and Takahashi render the method of claim 1 obvious, but do not teach that the first or second solvents comprise gamma-butyrolactone.
Taniguchi is directed to a method of producing purified anhydrous gamma-butyrolactone (para [0003]-[0005], [0010]-[0012]; para [0034] the gamma-butyrolactone is anhydrous), the method comprising steps of (1) synthesizing a crude gamma-butyrolactone, (2) purifying the crude gamma-butyrolactone by fractional distillation, and (3), further purifying the gamma-butyrolactone product of step 2, by flowing it through an ion exchange resin which adsorbs salts and other impurities from the gamma-butyrolactone (para [0026]-[0029], [0153]-[0156]). It follows that the ion exchange resin used in Taniguchi’s process will eventually become depleted and require regeneration, and when it does, it will contain adsorbed ion species and will be wet with a first organic solvent wherein the first organic solvent is gamma-butyrolactone.
It would have been obvious to a person having ordinary skill in the art before the effective filing date of the claimed invention to apply the ion exchange resin regeneration method of Shown and Takahashi to a resin that has been used in the treatment of gamma-butyrolactone, as disclosed in Taniguchi, because Taniguchi teaches there is a need for high purity anhydrous gamma-butyrolactone in the art (para [0002]-[0005]), and teaches using ion exchange resin to remove impurities from anhydrous gamma-butyrolactone (para [0029], [0153]-[0155]), and, Shown and Takahashi’s method is adapted for regenerating ion exchange resin that was used in the treatment of organic solutions without introducing water as an impurity into the organic solution when the ion exchange resin is placed back into operation. The application of Shown and Takahashi’s method to a resin that is wet with gamma-butyrolactone broadens the utility of the method by extending it to another industrially valuable solvent system. The claimed limitations are obvious because all the claimed elements were known in the prior art and one skilled in the art could have combined the elements as claimed by known methods with no change in their respective functions, and the combination yielded nothing more than predictable results [MPEP 2143(A)].
Claims 8-9 are rejected under 35 U.S.C. 103 as being unpatentable over Shown and Takahashi as applied to claim 1 above, and further in view of “Sifniades” (US 3,941,776 A to Sifniades et al).
Regarding claims 8-9, Shown and Takahashi render the method of claim 1 obvious, but do not teach the acid is a strong acid (as required by claim 8) or that the acid is HCl (as required by claim 9).
Sifniades is directed to a method for synthesizing an optically active aminocaprolactam compound, the method comprising a step of passing a reaction mixture in organic solvent (figure 1, reaction mixture stream comprising NiCl2, aminocaprolactam hydrochloride, and methanol/ethanol solvent) through an ion exchange column comprising hydroxide-form basic ion exchange resin (figure 1, ion exchange column VIII) to absorb HCl therefrom and thereby neutralize the reaction mix (col 5 ln 50-57; col 11 ln 4-10, col 16 ln 10-19). Sifniades teaches that the ion exchange resin subsequently needs to be regenerated, and that a regeneration procedure comprises treating the resin with a base solution to remove absorbed HCl therefrom (col 11 ln 10-14, figure 1, regenerant stream 30 of NH3 in methanol is passed through the ion exchange resin to regenerate the resin to its base form, and remove HCl therefrom as stream 25 of NH4Cl in methanol). It follows that the ion exchange resin of Sifniades, prior to its regeneration, is a resin that comprises an organic solvent (col 8 ln 21-34, the solvent that Sifniades is passing through the resin is alcohol, preferably ethanol, preferably anhydrous) and adsorbed HCl, i.e. an ionic species which is a strong acid (as required by claim 8) and which is HCl (as required by claim 9).
It would have been obvious to a person having ordinary skill in the art before the effective filing date of the claimed invention to apply the regeneration method of Shown and Takahashi to the ion exchange resin of Sifniades, which comprises an adsorbed acid that is a strong acid that is HCl, because Shown and Takahashi’s method is adapted for regenerating ion exchange resin that was used in the treatment of organic solutions without introducing water as an impurity into the organic solution when the ion exchange resin is placed back into operation (as taught in Takahashi at para [0280], [0297]), and Sifniades teaches their resin is need of regeneration (col 11 ln 10-14), and Sifniades is using their resin for the ion exchange treatment of an organic solution that is preferably free of water (col 8 ln 26-34). The application of Shown and Takahashi’s method to Sifniades’ resin broadens the utility of the method by extending it to another industrially valuable solvent system. The claimed limitations are obvious because all the claimed elements were known in the prior art and one skilled in the art could have combined the elements as claimed by known methods with no change in their respective functions, and the combination yielded nothing more than predictable results [MPEP 2143(A)].
Claims 10-11 are rejected under 35 U.S.C. 103 as being unpatentable over Shown and Takahashi as applied to claim 1 above, and further in view of “Salmon” (US 6,033,808 A to Salmon et al).
Regarding claim 10, Shown and Takahashi render the method of claim 1 obvious, but do not teach the first organic solvent further comprises alkali metal salts.
Salmon is directed to a method of removing acid from a lithium battery electrolyte solution in organic solvent by contacting the electrolyte solution with an ion exchange resin which absorbs the acid (col 2 ln 30-34). Salmon teaches that the electrolyte solution comprises organic solvent and lithium salts (col 3 ln 9-18). Salmon teaches that the ion exchange resin can be regenerated by washing with a regenerant to strip the acid therefrom, and reused (col 2 ln 38-40, col 4 ln 51-65). Salmon also teaches that the electrolyte solution should be kept free of water (col 1 ln 40 – col 2 ln 7).
It would have been obvious to a person having ordinary skill in the art before the effective filing date of the claimed invention to use the regeneration method disclosed in Shown and Takahashi to regenerate the ion exchange resin of Salmon, because Salmon uses their resin to treat an organic solution (col 2 ln 45-49) and stresses the need to minimize the amount of water in the solution (col 1 ln 40 – col 2 ln 7), and the method of Shown and Takahashi is disclosed as being suitable for resins that are intended for use in the treatment of organic solutions without introducing water as an impurity into the organic solution when the ion exchange resin is placed back into operation. The application of Shown and Takahashi’s method to Salmon’s resin broadens the utility of the base method by extending it to another industrially valuable solvent system. The claimed limitations are obvious because all the claimed elements were known in the prior art and one skilled in the art could have combined the elements as claimed by known methods with no change in their respective functions, and the combination yielded nothing more than predictable results [MPEP 2143(A)].
Regarding claim 11, Shown, Takahashi, and Salmon render the method of claim 10 obvious. The alkali metal salt that is in the organic solvent is, tautologically, alkali metal salt that has not been removed from the organic solvent. Therefore it is necessarily true that none of the alkali metal salt in the organic solvent has been removed from the solvent by the ion exchange resin; therefore, less than 50 wt% of the alkali metal salt in the organic solvent has been removed from the solvent by the ion exchange resin.
Claims 12-13 are rejected under 35 U.S.C. 103 as being unpatentable over Shown and Takahashi as applied to claim 1 above, in view of Salmon, and further in view of “Aurbach” (Aurbach et al, J. Electroanal. Chem., 339, 451-471 (1992)).
Regarding claim 12, Shown and Takahashi render the method of claim 1 obvious, but do not teach the first organic solvent further comprises dissolved carbon dioxide.
Salmon is directed to a method of removing acid from a lithium battery electrolyte solution in organic solvent by contacting the electrolyte solution with an ion exchange resin which absorbs the acid (col 2 ln 30-34).
Salmon teaches that the electrolyte solution comprises organic solvent and lithium salts (col 3 ln 9-18). Particularly the organic solvent may be ethyl carbonate or a mix of alkyl carbonates (col 3 ln 1-18; col 5 ln 62 – col 6 ln 11).
Salmon teaches that the ion exchange resin can be regenerated by washing with a regenerant to strip the acid therefrom, and reused (col 2 ln 38-40, col 4 ln 51-65).
Salmon also teaches that the electrolyte solution should be kept free of water (col 1 ln 40 – col 2 ln 7).
Aurbach teaches that, when a lithium battery electrolyte solution in ethylene carbonate or propylene carbonate solvent contains dissolved CO2, the efficiency of lithium cycling is improved. (pg 470 para 2-4, “Conclusion ... When CO2 is present in solution its reduction on the lithium surface forms Li2CO3 ... The presence of Li,CO, on the lithium surfaces increases the lithium cycling efficiency considerably”). Aurbach suggests that the addition of CO2 to the electrolyte may be intentionally pursued for this reason (pg 470 para 4 “the Li cycling efficiency may be increased considerably by the use of active additives”).
It would have been obvious to a person having ordinary skill in the art before the effective filing date of the claimed invention to use the regeneration method disclosed in Shown and Takahashi to regenerate the ion exchange resin of Salmon, which contains a lithium battery electrolyte solution of lithium salts in ethylene carbonate, because Salmon uses their resin to treat an organic solution (col 2 ln 45-49) and stresses the need to minimize the amount of water in the solution (col 1 ln 40 – col 2 ln 7), and the method of Shown and Takahashi is disclosed as being suitable for resins that are intended for use in the treatment of organic solutions without introducing water as an impurity into the organic solution when the ion exchange resin is placed back into operation. The application of Shown and Takahashi’s method to Salmon’s resin broadens the utility of the base method by extending it to another industrially valuable solvent system.
Moreover, since Salmon is directed to a alkyl carbonate-based solution for use as a lithium battery electrolyte, it would have been obvious to a person having ordinary skill in the art before the effective filing date of the claimed invention to include CO2 in Salmon’s solution, based on Aurbach’s teaching that the efficiency of lithium cycling in ethyl carbonate electrolyte is improved by the inclusion of CO2 in the electrolyte.
The claimed limitations are obvious because all the claimed elements were known in the prior art and one skilled in the art could have combined the elements as claimed by known methods with no change in their respective functions, and the combination yielded nothing more than predictable results [MPEP 2143(A)].
Regarding claim 13, Shown, Takahashi, Salmon and Aurbach render the method of claim 12 obvious. The carbon dioxide that is in the organic solvent is, tautologically, carbon dioxide that has not been removed from the organic solvent. Therefore it is necessarily true that, of the carbon dioxide remaining in the organic solvent at the time the regeneration method is carried out, none has been removed from the solvent by the ion exchange resin; therefore, less than 50 wt% of the carbon dioxide in the organic solvent has been removed from the solvent by the ion exchange resin.
Claims 23-24 are rejected under 35 U.S.C. 103 as being unpatentable over Shown and Takahashi as applied to claim 1 above, and further in view of “Tanaka” (US 6,911,481 B2 to Tanaka et al).
Regarding claim 22, Shown and Takahashi render the method of claim 1 obvious. Shown does not teach the step of backwashing the ion exchange resin comprising adsorbed ionic species to remove suspended solids.
Tanaka teaches a method of regenerating ion exchange resin comprising a step of backwashing the ion exchange resin comprising adsorbed ionic species to remove suspended solids. Tanaka teaches that, compared to a method that does not include backwashing, the method that does include backwashing is advantageous because it provides a more thorough cleaning of the resin (col 2 ln 18 - col 3 ln 3).
It would have been obvious to a person having ordinary skill in the art before the effective filing date of the claimed invention to incorporate, into the ion exchange resin regeneration method of Shown and Takahashi, a step of backwashing the ion exchange resin, based on Tanaka’s teaching that, compared to a method that does not include backwashing, the method that does include backwashing is advantageous because it provides a more thorough cleaning of the resin (col 2 ln 18 - col 3 ln 3).
Claims 23-24 are rejected under 35 U.S.C. 103 as being unpatentable over Shown and Takahashi as applied to claim 1 above, and further in view of “Bader” (US 6,827,858 B2 to Bader et al).
Regarding claim 23, Shown and Takahashi render the method of claim 1 obvious, but do not teach the adsorbed ionic species is a base.
Bader is directed to a method of purifying an alkoxylate compound, to remove therefrom an ionic impurity which is a base (col 1 ln 7-20, “Alkoxylates ... are prepared by catalysis using potassium hydroxide ... the catalyst must be separated off”; col 1 ln 47-57). Bader’s method comprises preparing a solution of the alkoxylate in an organic solvent, then contacting the solution with an ion exchange resin so that the ionic species is adsorbed to the resin (col 1 ln 55-65). Bader also teaches that, after carrying out this separation process for a time, the ion exchange needs to be regenerated to remove the adsorbed species (col 3 ln 7-14). The regeneration method may comprise draining the remaining organic solution from the resin, washing the resin with aqueous regenerant solution, then removing residual by displacing it with clean organic solvent (col 3 ln 15-37).
It would have been obvious to a person having ordinary skill in the art before the effective filing date of the claimed invention to extend the utility of Shown’s ion exchange resin regeneration method by applying it to the ion exchange resin of Bader, which is employed to adsorb an ionic species that is a base, based on Bader’s teaching that their ion exchange resin is in need of regeneration, and that a suitable regeneration method may be one which, like Shown’s method, comprises steps of washing the organic-solvent containing resin with an aqueous regenerant, then removing the water and reintroducing the organic solvent. The claimed limitations are obvious because all the claimed elements were known in the prior art and one skilled in the art could have combined the elements as claimed by known methods with no change in their respective functions, and the combination yielded nothing more than predictable results [MPEP 2143(A)].
Regarding claim 24, Shown and Takahashi in view of Bader render the method of claim 23 obvious. Bader further teaches that their ion exchange resin comprises acid functional groups (col 2 ln 55-58, “Particularly suitable cation exchangers are strongly acidic, macroporous resins, for example those based on crosslinked polystyrenes having sulfonic esters as functional groups”).
Claim 25 is rejected under 35 U.S.C. 103 as being unpatentable over “Grant” (US 2019/0109322 A1 to Grant et al), in view of Salmon and Shown.
Regarding claim 25, Grant teaches a method of alkaliating a material in an anhydrous organic solvent (para [0008], [0045]) comprising the steps:
(a) providing the material (para [0014], [0045]);
(b) providing a bath comprising an anhydrous organic solvent having at least one dissolved alkali halide salt, wherein said bath contacts the material, preferably in a continuous process, and wherein a dry gas blanket covers said bath (para [0020], [0045]);
(c) providing an electrolytic field plate comprising an inert conductive material wherein said field plate establishes a field between the anode and the field plate (para [0021]); and
(d) applying a reducing current to the anode and an oxidizing current to the field plate (para [0022]), wherein alkali ions from the bath alkaliate into the anode (para [0022], “metal ions will lithiate the material, e.g. anode”) and an anhydrous organic solvent comprising acid byproducts is formed (para [0050]-[0052], a halogen byproduct is formed, which can further react with e.g. trace water in the organic solvent to form an acid byproduct in the solvent, e.g. HCl).
Grant does not teach (e) contacting the anhydrous organic solvent comprising acid byproducts with an ion exchange resin comprising base residues thereby producing an ion exchange resin comprising an adsorbed ion species and an anhydrous organic solvent teaches; (f) adding a regenerant to the ion exchange resin comprising adsorbed ionic species and organic solvent; (g) washing the ion exchange resin with an aqueous solution; (h) removing the water to produce a dried ion exchange resin; and wetting the dried ion exchange resin with the anhydrous organic solvent to regenerate the ion exchange resin.
Salmon teaches that acid byproducts in a lithium battery electrolyte solution catalyze decomposition of the electrolyte, and therefore it is desirable to remove them (col 1 ln 18 – col 2 ln 7). Salmon teaches a method of removing acid byproducts from a lithium battery electrolyte solution in organic solvent (col 2 ln 30-34), the method comprising:
(e) contacting the anhydrous organic solvent comprising acid byproducts with an ion exchange resin comprising base residues thereby producing an ion exchange resin comprising an adsorbed ion species and an anhydrous organic solvent (col 2 ln 30-40, “The process for removing acidic species from a lithium salt solution comprises contacting a solution comprising a lithium salt, a solvent, and at least one acidic species, with a weak base resin to remove the acidic species from the lithium salt solution”; per col 3 ln 12-18, the solvent is organic; per col 1 ln 40 - col 2 ln 7 and col 4 ln 66 – col 5 ln 12, the solvent should be anhydrous);
(f) adding a regenerant to the ion exchange resin comprising adsorbed ionic species and organic solvent (col 4 ln 51-62), and washing the ion exchange resin with the regenerant solution to regenerate the ion exchange resin.
Salmon also teaches (h) removing water from the ion exchange resin to produce a dried ion exchange resin, before contacting the ion exchange resin with the anhydrous organic solvent (col 3 ln 51-60).
It would have been obvious to a person having ordinary skill in the art before the effective filing date of the claimed invention to modify the method of Grant by incorporating the steps of contacting the anhydrous organic solvent comprising acid byproducts with an ion exchange resin comprising base residues thereby producing an ion exchange resin comprising an adsorbed ion species and an anhydrous organic solvent, and regenerating the ion exchange resin to remove the adsorbed acids therefrom, as taught in Salmon, based on Salmon’s teaching that acid byproducts in an anhydrous lithium electrolyte solution are harmful and should be removed, and that ion exchange with a basic ion exchange resin is an effective way to remove them.
Salmon does not teach that the regeneration sequence includes washing the ion exchange resin with an aqueous solution.
Shown is similarly directed to using an ion exchange resin to remove acids from an organic solvent medium (para [0044], “highly acidic crude oil is treated with ion-exchange resin for neutralization and desalting”; para [0060]-[0065]), and a method for regenerating said ion exchange resin (para [0042], “a method of treatment of at least partially spent ion-exchange resin to obtain regenerated ion-exchange resin”). Shown’s method comprises:
- providing an ion exchange resin comprising an absorbed ion species and a first organic solvent (para [0045], “the obtained spent ion-exchange resin is contacted with at least one non-acidic crude oil condensate, to obtain partially cleansed ion-exchange resin, followed by at least one polar organic solvent to obtain heavy hydrocarbon free ion-exchange resin. The non-acidic lighter crude oil condensate and the polar organic solvent do not interact with acids and salts adhered on the ion-exchange resin. However, they selectively remove the adhered compounds such as asphaltenes”; i.e., the ion exchange resin, after this step, comprises an organic solvent and also still has ionic species absorbed to it; para [0075]),
- adding a regenerant and at least one solution comprising water to the ion exchange resin comprising adsorbed ionic species and organic solvent to produce a regenerated ion exchange resin (para [0051], “In the next step, the heavy hydrocarbon free ion-exchange resin is treated with at least one alkali or alkaline earth metal hydroxide solution to obtain activated ion-exchange resin”; para [0077], “5 wt % 5 BV aqueous caustic solution was passed through the packed resin ... the resin bed was washed with demineralized water”),
- placing the regenerated ion exchange membrane into service by wetting it with a process solution comprising a second organic solvent (para [0078], “The resin obtained was tested for its recyclability by subjecting it iteratively to the similar process as mentioned in Experiment 1 step C. It was found that resin could be recycled for 34 times”; para [0060]-[0065], Experiment 1 step C involves passing an acidic crude oil through the ion exchange resin to absorb acids and salts from the oil onto the resin).
It would have been obvious to a person having ordinary skill in the art before the effective filing date of the claimed invention, when carrying out the ion exchange resin regeneration in the method of Grant and Salmon, to include a step of washing the ion exchange resin with an aqueous regenerant solution, based on Shown’s teaching that this is an effective way to remove adsorbed acids from ion exchange resin, and the resin treated this way is suitable for use in the removal of acids from organic solvents. In so doing it would be obvious to carry out the step (h) of drying the washed ion exchange resin to remove water therefrom, then wetting with the anhydrous solvent, taught in Salmon (col 3 ln 51-60), after the step of washing the resin with aqueous solution as taught in Shown, based on Salmon’s teaching that it is desirable to keep water out of the anhydrous solvent (col 3 ln 51-60; col 4 ln 66 – col 5 ln 12). The claimed limitations are obvious because all the claimed elements were known in the prior art and one skilled in the art could have combined the elements as claimed by known methods with no change in their respective functions, and the combination yielded nothing more than predictable results [MPEP 2143(A)].
Conclusion
The art made of record and not relied upon is considered pertinent to applicant's disclosure. US 2024/0157354 A1 to Takada et al discloses every limitation of claim 1. Takada is not considered prior art here, because Takada’s disclosure was filed on the same date as the provisional US application to which the instant application makes a priority claim. However, Takada’s corresponding international application may be considered prior art in other jurisdictions.
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/ANDREW KOLTONOW/Examiner, Art Unit 1795
/LUAN V VAN/Supervisory Patent Examiner, Art Unit 1795