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 69-78 and 80-88 are pending in this application. Claims 69-78 and 80-87 are under examination herein. Claim 88 is withdrawn from consideration. Claims 1-68 and 79 have been cancelled by applicant.
Examiner Notes
Claim 83 has no prior art rejections herein, however, it stands rejected under the obviousness-type non-statutory double patenting rejections of record.
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 69-78, 80-82, and 84-87 are rejected under 35 U.S.C. 103 as being unpatentable over Singer et al. (WO 2007/071028 A1 – From IDS – previously cited) (“Singer”); in view of Chatel et al. (Green Chem., 2014, 16, 2051–2083) (“Chatel”); and Ralston et al. (WO 2012/079129 A1 – previously cited) (“Ralston”).
Regarding instant claims 69 and 84, Singer discloses compounds that can be useful as ligands and ionic liquids with a general Formula (I) (pages 3-5 and claim 1). Singer discloses a metal extraction process comprising a step of complexing the metal with at least one of their compounds (page 5, last para.) – reading on a composition comprising two ionic liquids and on the intended use of the instant invention.
PNG
media_image1.png
157
157
media_image1.png
Greyscale
Wherein; R1 is a positively charged heterocyclic ring (Corresponding to [Y+]). Singer defines “heterocyclyl” as non-aromatic rings or ring systems that contain at least one ring having at least one hetero-atom (N, O, S) (page 8, last para.), reading on the instant ionic liquids when [Y+] is piperidinium, morpholinium, etc. X2 and X3 can be O and R2 and R3 can be -N(R5)2, wherein R5 is C1-20 alkyl (reading on EDG being -C(O)NRyRx, wherein Ry and Rx are C3-6 alkyl); X1 is an anion (corresponding to [X-]); m is an integer having a value from 1 to 3; (corresponding to L2); n is an integer having a value from 1 to 3; (corresponding to L2); p is an integer having a value from 1 to 12 (corresponding to L1);
Singer discloses the ILs below (page 22), which differ from the IL in the instantly claimed composition only in that the group corresponding to the R2-3 in Formula I above is -OtBu instead of -NRxRy (as required by the instant claims, wherein EDG is -C(O)NRxRy); Singer, however, discloses that their R2-3 in their Formula I, can also be -NRxRy. Thus, Singer discloses a relatively broad genus of compounds which encompass the instant subgenus.
PNG
media_image2.png
297
447
media_image2.png
Greyscale
Therefore, one having ordinary skill in the art would have found the IL in the claimed composition prima facie obvious, since they are generically embraced by Singer’s disclosed formula; In re Susi, 440 F.2d 442, 169 USPQ 423 (CCPA 1971). See MPEP 2144.08. The requisite motivation for arriving at the claimed compounds stems from the fact that they fall within the generic class of compounds disclosed by Singer. Accordingly, one having ordinary skill in the art would have been motivated to prepare any of the compounds embraced by the disclosed generic formula, including those encompassed by the claims.
Furthermore, a novel useful compound that is isomeric with the prior art compound is unpatentable unless it possesses some unobvious or unexpected beneficial property not possessed by the prior art compound. In re Norris, 179 F.2d. 970, 84 USPQ 458 (CCPA 1970). Therefore, it would have been obvious to one of ordinary skill to expect similar properties of structurally similar compounds since they are suggestive of one another. It has been held that a compound, which is structurally isomeric with a compound of the prior art, is prima facie obvious absent unexpected results. In re Finely, 81 USPQ 383 (CCPA 1949); 84 USPQ 458 (CCPA 1950).
While Singer doesn’t specifically teach: (i) mixtures of their ionic liquid (IL) of Formula (I) with another lower viscosity ionic liquid at concentrations of 0.001-0.01 M; or (ii) the ionic liquid further comprising an organic solvent; the teachings of Chatel and Ralston are relied upon for these disclosures.
Chatel discloses general trends in viscosity of different molar ratios of “double salt ionic liquids” (DSIL) and deviations of viscosity from the mixing averages of the two parent IL (table 2). Chatel further discloses higher ionic conductivity for some three-ion DSILs (Table 4, entries 1 and 5–7) and four-ion DSILs (Table 4, entry 10) compared to either of the two-ion IL parents, which suggests unique properties are accessible by the DSIL approach compared to any series of two-ion ILs (page 2058, col. 2, section 2.3, para. 2). Furthermore, Chatel discloses, for example, [C2C1im][NTf2] as a low viscosity IL (reading on imidazolium lower viscosity ionic liquid – claim 84) (page 2056, col. 1).
Ralston teaches that gold ions can be extracted from an aqueous phase using an extractant phase comprising an ionic liquid with a miscible volatile organic solvent (page 1, lines 26-29, and Ralston claims 6 and 8). Ralston explores the extraction efficiency of gold from an aqueous solution utilizing different concentrations of an ionic liquid in chloroform (page 13, lines 14-27) – pure ionic liquid had a much slower flow rate but was able to extract 95% of the gold from the solution, while 2 v/v% ionic liquid in chloroform managed to extract 91% of the gold from the solution with a much faster flow rate. Example 4 (page 14, lines 17-22) further show the efficiency of diluted ionic liquid in chloroform in extracting gold from an HCl solution.
Therefore, regarding amended claims 69 and 84, it would have been prima facie obvious to one of ordinary skill prior to the effective filing date of the claimed invention to prepare a composition comprising an ionic liquid and a lower viscosity ionic liquid in view of Singer, further in view of Chatel and Ralston. One of ordinary skill would have been motivated to do so because Singer discloses their ionic liquids of Formula I above and discloses a metal extraction process comprising a step of complexing the metal with at least one of their compounds (reading on two IL); further because Chatel discloses mixtures of IL often resulted in viscosities lower than those of the parent ILs and higher conductivities; and further because Ralston discloses a motivation for finetuning the viscosity of an IL solution for the purposes of improving flow rate in a metal extraction system. One of ordinary skill would have had a reasonable expectation of success because Singer discloses the ILs of Formula I and mixtures thereof; Chatel discloses trends on viscosity of ionic liquid mixtures at molar ratios of 0.25, 0.5, and 0.75; and Ralston’s suggests the positive effects of lower viscosity on flow rate while retaining metal extraction capabilities, after switching from pure ionic liquid to 2% v/v in chloroform and observing relative extractions of 95% and 91% respectively.
While Singer in view of Chatel and Ralston do not specifically disclose concentrations of 0.001-0.01 M; Chatel discloses molar ratios of 0.25, 0.5, and 0.75 of DSIL mixtures and Ralston discloses concentrations of 2% v/v in organic solvents. Thus, Applicant is advised that the courts have stated where the claimed ranges overlap or lie inside the ranges disclosed by the prior art and even when the claimed ranges and prior art ranges do not overlap but are close enough that one skilled in the art would have expected them to have similar properties, a prima facie case of obviousness exists. See In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990); Titanium Metals Corp. of America v. Banner, 778 F2d 775. 227 USPQ 773 (Fed. Cir. 1985) (see MPEP 2144.05.01). The courts have also found that 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. See In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955). See MPEP 2144.05-II.
Therefore, the claimed ranges merely represent an obvious variant and/or routine optimization of the values of the cited prior art.
Furthermore, it is noted that In re Best (195 USPQ 430) and In re Fitzgerald (205 USPQ 594) discuss the support of rejections wherein the prior art discloses subject matter which there is reason to believe includes functions that are newly cited or is identical to a product instantly claimed. In such a situation the burden is shifted to the applicants to “prove that subject matter shown to be in the prior art does not possess the characteristic relied on” (205 USPQ 594, second column, first full paragraph). In the present case, Applicant would need to show that claimed concentration ranges work exceptionally well for metal extractions compared to concentration values that deviate from claimed values.
In addition, regarding the composition comprising two ILs, one with lower viscosity, the courts have found that “[i]t is prima facie obvious to combine two compositions each of which is taught by the prior art to be useful for the same purpose, in order to form a third composition to be used for the very same purpose.... [T]he idea of combining them flows logically from their having been individually taught in the prior art (In re Kerkhoven, 626 F.2d 846, 850, 205 USPQ 1069, 1072 (CCPA 1980).” See MPEP2144.06. It is therefore obvious to provide a mixture of the two agents.
Regarding claim 70, Singer discloses the ionic liquids of Formula I can coordinate or chelate with metals to form complexes and can be used in applications in which metal removal is required (page 4, second to last para. lines 1-4; and claim 50). Singer also discloses their compound of Formula (I) complexing with a metal center in a tridentate fashion, affording complexes like Formula (VII), showing a 5- or 6-membered ring with the metal center when r is 1 or 2, respectively.
PNG
media_image3.png
204
188
media_image3.png
Greyscale
Regarding instant claim 71, Singer further discloses that, in the compounds of Formula (I) discussed above, the R1 group can be acyclic cations: —[N(R8) (R9) (R10)]+; —[P(R11) (R12) (R13)]+; or —[S(R14) (R15)]+ (page 9, para. 4).
Regarding claim 72, Singer discloses their compounds of Formula I wherein R1 can be
PNG
media_image4.png
82
70
media_image4.png
Greyscale
,
PNG
media_image5.png
81
66
media_image5.png
Greyscale
,
PNG
media_image6.png
83
61
media_image6.png
Greyscale
, or
PNG
media_image7.png
80
76
media_image7.png
Greyscale
, etc. (page 9, para. 4; and claim 6).
Regarding claims 73 and 76, Singer discloses their compound of Formula I wherein R1 can be heterocyclyl, like morpholinyl, piperidinyl, pyrrolidinyl, etc., which can be unsubstituted or substituted with 1 to 3 substituents selected from the group consisting of C1-C20 alkyl, C6-C12 aryl, C3-C8 cycloalkyl.
Regarding claim 74-75, Singer discloses their compound of Formula I wherein the R1 heterocycle can be substituted with 1 to 3 substituents selected from the group consisting of -COOH, -COOR4, wherein R4 can be C1-C20 alkyl, (corresponding to
PNG
media_image8.png
101
107
media_image8.png
Greyscale
, wherein Rx can be C3-6 alkyl).
Regarding claim 77, Singer discloses their compound of Formula I wherein p can have a value from 1 to 12 (corresponding to L1 being C-1-10 alkanediyl).
Regarding claim 78, Singer discloses their compound of Formula I wherein n and m can have a value from 1 to 3 (corresponding to L1 being C-1-2 alkanediyl).
Regarding claim 80, Singer discloses their compound of Formula I wherein X2 and X3 can be O and R2 and R3 can be -N(R5)2, wherein R5 are C1-C20 alkyl (corresponding to
PNG
media_image9.png
88
103
media_image9.png
Greyscale
).
Regarding claim 81-82, Singer discloses their compound of Formula I wherein X1 is an anion (corresponding to [X-]) selected from the group consisting of F-, Cl-, Br-, I-, (CN)2N-, BF4-, SbF6-, BH4-, AsF6-, CH3COO-, CF3COO-, CH3SO3-, CF3SO3-, FSO3-, (FSO2)2N-, (C2F5SO2)2N-, NO3-, N3-, ClO4-, TsO- (tosylate), NsO- (nosylate), HSO42-, [MX4]-, [M2X7]- (wherein M is a metal such as iron and X is F-, Cl-, Br-, I-, or (C2F5SO2)2N and PF6-.
Regarding claim 85, Singer discloses their compounds of Formula I wherein [X-] can be (CN)2N-, CH3COO-, CH3SO3-, NO3-, N3-, TsO- (tosylate), NsO- (nosylate), HSO42-, etc. (claim 1 of Singer) (reading on less than 25% halide and suggesting 0% halide content).
Applicant is reminded that that the courts have stated where the claimed ranges overlap or lie inside the ranges disclosed by the prior art and even when the claimed ranges and prior art ranges do not overlap but are close enough that one skilled in the art would have expected them to have similar properties, a prima facie case of obviousness exists. The courts have also found that 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.
Therefore, the claimed ranges merely represent an obvious variant and/or routine optimization of the values of the cited prior art.
Regarding claim 86, it would have been prima facie obvious to one of ordinary skill prior to the effective filing date of the instant application to use an ionic liquid further diluted in an organic solvent. One of ordinary skill in the art would have been motivated to do so in order to improve flow rates of the otherwise viscous pure ionic liquid or to use less of what may be a difficult and expensive to synthesize ionic liquid for the purposes of extracting precious metals from solutions. One of ordinary skill in the art would have had a reasonable expectation of success in using Singer’s compounds of Formula (I) in view of Ralston’s teachings that ionic liquids can be diluted with an organic solvent, such as chloroform, to extract metals from an aqueous solution.
Regarding claim 87, Singer discloses the complex of Formula (VII) above, wherein M is selected from the group of: Sc, Y, La, Ce, Pr, Nd, Pm, Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb, and Lu (rare earth metals). Singer also discloses a process comprising a step of complexing a metal with at least one compound of Formula (I), wherein a metal can be removed from a composition or solution comprising a solvent and the metal. Therefore, it would have been prima facie obvious to one of ordinary skill prior to the effective filing date of the instant application to use Singer’s compounds of Formula (I), either pure or further diluted by an organic solvent, as taught by Ralston, to extract metals from solutions. One of ordinary skill would have been motivated to do so and had a reasonable expectation of success in view of Singer’s disclosure of the metal complexes of Formula (VII).
Double Patenting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claims 69-78 and 80-87 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-21 of U.S. Patent No. 12,024,756 B2 (US ‘756); in view of Singer et al. (WO 2007/071028 A1 – From IDS).
Regarding instant claims 69-78 and 80-87, US ‘756 claims a method of extracting rare earth metals from a mixture of one or more rare earth metals by contacting an acidic solution with the one of the ionic liquids below (US ‘756 claims 1 and 20); and claims their method further comprising a lower viscosity ionic liquid and/or an organic solvent (US ‘756 claim 21) – thus rendering the instant composition obvious.
PNG
media_image10.png
126
116
media_image10.png
Greyscale
PNG
media_image11.png
182
157
media_image11.png
Greyscale
While US ‘756 does not specifically disclose concentrations of 0.001-0.01 M; Applicant is reminded that that the courts have stated where the claimed ranges overlap or lie inside the ranges disclosed by the prior art and even when the claimed ranges and prior art ranges do not overlap but are close enough that one skilled in the art would have expected them to have similar properties, a prima facie case of obviousness exists. The courts have also found that 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.
Therefore, the claimed ranges merely represent an obvious variant and/or routine optimization of the values of the cited prior art.
Furthermore, it is noted that In re Best (195 USPQ 430) and In re Fitzgerald (205 USPQ 594) discuss the support of rejections wherein the prior art discloses subject matter which there is reason to believe includes functions that are newly cited or is identical to a product instantly claimed. In such a situation the burden is shifted to the applicants to “prove that subject matter shown to be in the prior art does not possess the characteristic relied on”. In the present case, Applicant would need to show that claimed concentration ranges work exceptionally well for metal extractions compared to concentration values that deviate from claimed values.
Regarding instant claim 70, US ‘576 speaks to the method of making rare earth metal oxide wherein the nitrogen linking L1 to each L2 and one of the EDG of the ionic liquid both coordinate to a metal to form a 5- or 6-membered metallocycle (US ‘579 claim 13).
While US ‘756 does not specifically mention wherein the ionic liquid anion content is less than 25% halides (claim 85); the teachings of Singer are relied upon for these disclosures.
Regarding claim 85, Singer discloses their compounds of Formula I wherein [X-] can be (CN)2N-, CH3COO-, CH3SO3-, NO3-, N3-, TsO- (tosylate), NsO- (nosylate), HSO42-, etc. (claim 1 of Singer) (reading on less than 25% halide and suggesting 0% halide content).
Therefore, it would have been prima facie obvious to one of ordinary skill to prepare the instantly claimed composition, since it is disclosed by US ‘756 in view of Singer. One of ordinary skill would have been motivated to do so, with a reasonable expectation of success in view of the disclosures above.
Regarding the claimed range of < 25% halide, Applicant is reminded that the courts have stated where the claimed ranges overlap or lie inside the ranges disclosed by the prior art and even when the claimed ranges and prior art ranges do not overlap but are close enough that one skilled in the art would have expected them to have similar properties, a prima facie case of obviousness exists. The courts have also found that 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.
Therefore, the claimed ranges merely represent an obvious variant and/or routine optimization of the values of the cited prior art.
Claims 69-78 and 80-87 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-20 of U.S. Patent No. 11,958,754 B2 (US ‘754); in view of Singer et al. (WO 2007/071028 A1 – From IDS).
Regarding instant claims 69-78 and 80-87, US ‘754 speaks to a method of extracting rare earth metals from a mixture of one or more rare earth metals by contacting an acidic solution with the one of the ionic liquids below (US ‘754 claims 1 and 14); US ‘754 further claims their method further comprising a lower viscosity ionic liquid and/or an organic solvent; and wherein the cation and anion of the IL are present at 0.001 M (US ‘754 claim 17) – thus rendering the instant composition obvious.
PNG
media_image10.png
126
116
media_image10.png
Greyscale
PNG
media_image11.png
182
157
media_image11.png
Greyscale
Regarding instant claim 70, US ‘754 speaks to the method of making rare earth metal oxide wherein the nitrogen linking L1 to each L2 and one of the EDG of the ionic liquid both coordinate to a metal to form a 5- or 6-membered metallocycle (US ‘754 claim 7).
While US ‘754 does not specifically mention wherein the ionic liquid anion content is less than 25% halides (claim 85); the teachings of Singer are relied upon for these disclosures.
Regarding claim 85, Singer discloses their compounds of Formula I wherein [X-] can be (CN)2N-, CH3COO-, CH3SO3-, NO3-, N3-, TsO- (tosylate), NsO- (nosylate), HSO42-, etc. (claim 1 of Singer) (reading on less than 25% halide and suggesting 0% halide content).
Therefore, it would have been prima facie obvious to one of ordinary skill to prepare the instantly claimed composition, since it is disclosed by US ‘754 in view of Singer. One of ordinary skill would have been motivated to do so, with a reasonable expectation of success in view of the disclosures above.
Regarding the claimed range of < 25% halide or 0.01-0.001 M IL concentrations, Applicant is reminded that the courts have stated where the claimed ranges overlap or lie inside the ranges disclosed by the prior art and even when the claimed ranges and prior art ranges do not overlap but are close enough that one skilled in the art would have expected them to have similar properties, a prima facie case of obviousness exists. The courts have also found that 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.
Therefore, the claimed ranges merely represent an obvious variant and/or routine optimization of the values of the cited prior art.
Claims 69-78 and 80-87 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-20 of U.S. Patent No. 11,401,579 B2 (US ‘579); in view of Singer et al. (WO 2007/071028 A1 – From IDS).
Regarding instant claims 69-78 and 80-87, US ‘579 claims a method of making a rare earth metal oxide comprising contacting an acidic solution of a metal mixture with an ionic liquid with one of the formulas below (US ‘579 claims 1 and 16); US ‘579 speaks to their method further comprising a lower viscosity ionic liquid and/or an organic solvent, and wherein the anion of the IL is present at least at 0.01 M (US ‘579 claim 18).
PNG
media_image12.png
127
121
media_image12.png
Greyscale
PNG
media_image13.png
170
137
media_image13.png
Greyscale
Regarding instant claim 70, US ‘579 claims method of making rare earth metal oxide wherein the nitrogen linking L1 to each L2 and one of the EDG of the ionic liquid both coordinate to a metal to form a 5- or 6-membered metallocycle (US ‘579 claim 10).
While US ‘579 does not specifically mention wherein the ionic liquid anion content is less than 25% halides (claim 85); the teachings of Singer et al. are relied upon for these disclosures.
Regarding claim 85, Singer discloses their compounds of Formula I wherein [X-] can be (CN)2N-, CH3COO-, CH3SO3-, NO3-, N3-, TsO- (tosylate), NsO- (nosylate), HSO42-, etc. (claim 1 of Singer) (reading on less than 25% halide and suggesting 0% halide content).
Therefore, it would have been prima facie obvious to one of ordinary skill to prepare the instantly claimed composition, since it is disclosed by US ‘759 in view of Singer. One of ordinary skill would have been motivated to do so, with a reasonable expectation of success in view of the disclosures above.
Regarding the claimed range of < 25% halide or 0.01-0.001 M IL concentrations, Applicant is reminded that the courts have stated where the claimed ranges overlap or lie inside the ranges disclosed by the prior art and even when the claimed ranges and prior art ranges do not overlap but are close enough that one skilled in the art would have expected them to have similar properties, a prima facie case of obviousness exists. The courts have also found that 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.
Therefore, the claimed ranges merely represent an obvious variant and/or routine optimization of the values of the cited prior art.
Claims 69-78 and 80-87 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claim 1, 5-10, 12, 14-17, 20-23, and 25-27 of copending Application No. 17/252,255 (Copending ‘255); in view of Singer et al. (WO 2007/071028 A1 – From IDS).
Regarding instant claims 69-78 and 80-87, Copending ‘255 speaks to a method of making the ionic liquid below, which reads on the instantly claimed ionic liquid (claim 1 of Copending ‘255). Copending ‘255 claims a method of extracting a rare earth metal with their IL, their method comprising a first IL and a second lower density IL, at concentrations of at least 0.001 M – reading on the instant composition (claims 21 and 27 of Copending ‘255).
PNG
media_image14.png
237
158
media_image14.png
Greyscale
While Copending ‘255 does not specifically mention wherein the ionic liquid anion content is less than 25% halides (claim 85); the teachings of Singer are relied upon for these disclosures.
Regarding claim 85, Singer discloses their compounds of Formula I wherein [X-] can be (CN)2N-, CH3COO-, CH3SO3-, NO3-, N3-, TsO- (tosylate), NsO- (nosylate), HSO42-, etc. (claim 1 of Singer) (reading on less than 25% halide and suggesting 0% halide content).
Therefore, it would have been prima facie obvious to one of ordinary skill to prepare the instantly claimed composition, since it is disclosed by Copending ‘255 in view of Singer. One of ordinary skill would have been motivated to do so, with a reasonable expectation of success in view of the disclosures above.
Regarding the claimed range of < 25% halide or 0.01-0.001 M IL concentrations, Applicant is reminded that the courts have stated where the claimed ranges overlap or lie inside the ranges disclosed by the prior art and even when the claimed ranges and prior art ranges do not overlap but are close enough that one skilled in the art would have expected them to have similar properties, a prima facie case of obviousness exists. The courts have also found that 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.
Therefore, the claimed ranges merely represent an obvious variant and/or routine optimization of the values of the cited prior art.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Response to Arguments
Claims
Claim amendments are acknowledged. No new matter has been introduced.
Applicant’s traversal of rejections is discussed below.
Claim Objections
Applicant’s arguments, see page 11, filed 12/15/2025, with respect to the objection to claim 85 have been fully considered and are persuasive. In light of the claim amendments, the objection to claim 85 has been withdrawn.
Claim Rejections - 35 USC § 112(b)
Applicant’s arguments, see pages 11-12, filed 12/15/2025, with respect to 35 USC § 112(b) rejection of the claims have been fully considered and are persuasive. The 35 USC § 112(b) rejection of the claims has been withdrawn.
Claim Rejections - 35 USC § 102
Applicant’s arguments, see pages 13-17, filed 12/15/2025, with respect to 35 USC § 102 rejection of the claims have been fully considered and are persuasive. In light of the claim amendments, the 35 USC § 102 rejection of the claims has been withdrawn.
Claim Rejections - 35 USC § 103
Applicant’s arguments, see pages 13-17, filed 12/15/2025, with respect to 35 USC § 103 rejection of the claims have been fully considered and are persuasive. In light of the claim amendments, the 35 USC § 103 rejection of the claims has been withdrawn. However, upon further consideration, and in view of claim amendments, a new ground(s) of rejection is made for claims 69-78, 80-82, and 84-87 in view of Singer, Chatel, and Ralston.
Applicant argues that there’s no evidence Singer contains a “clear disclosure of a composition according to claim 69 in which an IL having EDG represents -C(O)NRxRy wherein Rx-y are C3-6 alkyl. Applicant cites MPEP 2131.02 (III) to state that a generic formula encompassing a vast number of compounds without more preferred substituents being disclosed would not anticipate a more specific compound. Applicant states that Singer mentions -N(R5)2 from a list of 8 possibilities for R2-3, then 10 possibilities for R5, and two possibilities for X2-3, and that there is no specific motivation to combine all these elements to arrive at the structures of amended claim 69. Applicant argues that Singer’s preferred embodiments show R2-3 as -OR6 only [wherein R6 is tBu], with the intention of deprotecting to coordinate to a metal, while the instant compounds are meant to coordinate to the metal without removal of the alkyl on the EDG. Applicant stated the embodiments of Singer are not consistent with the purpose and properties of the instant composition. Applicant states that none of the cited references disclose or teach providing the claimed IL in a lower viscosity liquid at a concentration of 0.01-0.001 M. Applicant points to the spec. (page 21, lines 13-19; page 27; and Figure 1) to demonstrate high separation factors and “highly effective separation of rare earth metals from other rare earth metals” which Applicant alleges is very different from what is taught in the cited art. Applicant states that Ralston teaches extraction of gold ions, citing page 8, lines 7-9 and Example 4 and Figure 11 to say that “below 2% the extraction falls sharply”. Applicant states that Singer only mentions extracting metal ions in general; and that none of the references provide extraction between different rare earth metals or how this could be achieved.
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).
Regarding Applicant’s arguments that Singer lacks a “clear disclosure of a composition according to claim 69”. Singer discloses their compounds of Formula (I) (pages 3-5 and claim 1) wherein R1 is a positively charged heterocyclic ring (Corresponding to [Y+]). Singer defines “heterocyclyl” as non-aromatic rings or ring systems that contain at least one ring having at least one hetero-atom (N, O, S) (page 8, last para.), reading on the instant ionic liquids when [Y+] is piperidinium, morpholinium, etc. X2 and X3 can be O and R2 and R3 can be -N(R5)2, wherein R5 is C1-20 alkyl (reading on EDG being -C(O)NRyRx, wherein Ry and Rx are C3-6 alkyl); X1 is an anion (corresponding to [X-]); m is an integer having a value from 1 to 3; (corresponding to L2); n is an integer having a value from 1 to 3; (corresponding to L2); p is an integer having a value from 1 to 12 (corresponding to L1);
PNG
media_image1.png
157
157
media_image1.png
Greyscale
Singer discloses the ILs below (page 22), which differ from the IL in the instantly claimed composition only in that the group corresponding to the R2-3 in Formula I above is -OtBu instead of -NRxRy (as required by the instant claims, wherein EDG is -C(O)NRxRy); Singer, however, also discloses that their R2-3 in their Formula I, can also be -N(R5)2, wherein R5 is C1-20 alkyl. Thus, Singer discloses a relatively broad genus of compounds which encompass the instant subgenus.
PNG
media_image2.png
297
447
media_image2.png
Greyscale
Therefore, one having ordinary skill in the art would have found the IL in the claimed composition prima facie obvious, since they are generically embraced by Singer’s disclosed formula. The requisite motivation for arriving at the claimed compounds stems from the fact that they fall within the generic class of compounds disclosed by Singer. Accordingly, one having ordinary skill in the art would have been motivated to prepare any of the compounds embraced by the disclosed generic formula, including those encompassed by the claims.
Applicant is reminded that a novel useful compound that is isomeric with the prior art compound is unpatentable unless it possesses some unobvious or unexpected beneficial property not possessed by the prior art compound. Therefore, it would have been obvious to one of ordinary skill to expect similar properties of structurally similar compounds since they are suggestive of one another. It has been held that a compound, which is structurally isomeric with a compound of the prior art, is prima facie obvious absent unexpected results.
Regarding Applicant’s arguments that Applicant’s structure is broad and no specific preferred embodiments match the instant structures, Applicant is advised that "The use of patents as references is not limited to what the patentees describe as their own inventions or to the problems with which they are concerned. They are part of the literature of the art, relevant for all they contain." In re Heck, 699 F.2d 1331, 1332-33, 216 USPQ 1038, 1039 (Fed. Cir. 1983) (quoting In re Lemelson, 397 F.2d 1006, 1009, 158 USPQ 275, 277 (CCPA 1968)). Furthermore, disclosed examples and preferred embodiments do not constitute a teaching away from a broader disclosure or nonpreferred embodiments. In re Susi, 440 F.2d 442, 169 USPQ 423 (CCPA 1971). "A known or obvious composition does not become patentable simply because it has been described as somewhat inferior to some other product for the same use." See MPEP 2123 I-II.
Regarding the instant composition, as disclosed in the 103 section above, Singer discloses their compounds as being useful as ionic liquids (see page 1, para. 1; and claim 36); and that one object of their invention was to provide a metal extraction process (see page 2, second to last para.; and page 5 last para.; and page 11, second to last para.), wherein a “metal can be removed from a composition of solution comprising a solvent and a metal … or for removing a contaminating metal from a composition”. Singer also discloses that the metal extraction can be done with a composition comprising at least one of their IL compounds, reading on a composition of two IL, as claimed.
Chatel discloses general trends in viscosity of different molar ratios of “double salt ionic liquids” (DSIL) and deviations of viscosity from the mixing averages of the two parent IL (table 2). Chatel further discloses higher ionic conductivity for some three-ion DSILs (Table 4, entries 1 and 5–7) and four-ion DSILs (Table 4, entry 10) compared to either of the two-ion IL parents, which suggests unique properties are accessible by the DSIL approach compared to any series of two-ion ILs (page 2058, col. 2, section 2.3, para. 2). Furthermore, Chatel discloses, for example, [C2C1im][NTf2] as a low viscosity IL (reading on imidazolium lower viscosity ionic liquid – claim 84) (page 2056, col. 1).
Ralston teaches that gold ions can be extracted from an aqueous phase using an extractant phase comprising an ionic liquid with a miscible volatile organic solvent (page 1, lines 26-29, and Ralston claims 6 and 8). Ralston explores the extraction efficiency of gold from an aqueous solution utilizing different concentrations of an ionic liquid in chloroform (page 13, lines 14-27) – pure ionic liquid had a much slower flow rate but was able to extract 95% of the gold from the solution, while 2 v/v% ionic liquid in chloroform managed to extract 91% of the gold from the solution with a much faster flow rate. Example 4 (page 14, lines 17-22) further show the efficiency of diluted ionic liquid in chloroform in extracting gold from an HCl solution.
Therefore, it would have been prima facie obvious to one of ordinary skill prior to the effective filing date of the claimed invention to prepare a composition comprising an ionic liquid and a lower viscosity ionic liquid in view of Singer, further in view of Chatel and Ralston. One of ordinary skill would have been motivated to do so because Singer discloses their ionic liquids of Formula I above and discloses a metal extraction process comprising a step of complexing the metal with at least one of their compounds (reading on two IL); further because Chatel discloses mixtures of IL often resulted in viscosities lower than those of the parent ILs and higher conductivities; and further because Ralston discloses a motivation for finetuning the viscosity of an IL solution for the purposes of improving flow rate in a metal extraction system. One of ordinary skill would have had a reasonable expectation of success because Singer discloses the ILs of Formula I and mixtures thereof; Chatel discloses trends on viscosity of ionic liquid mixtures at molar ratios of 0.25, 0.5, and 0.75, and teaches [C2C1im][NTf2] as a low viscosity imidazolium IL; and Ralston’s suggests the positive effects of lower viscosity on flow rate while retaining metal extraction capabilities, after switching from pure ionic liquid to 2% v/v in chloroform.
While Singer in view of Chatel and Ralston do not specifically disclose concentrations of 0.001-0.01 M; Chatel discloses molar ratios of 0.25, 0.5, and 0.75 of DSIL mixtures and Ralston discloses concentrations of 2% v/v in organic solvents. Thus, Applicant is reminded that the courts have stated where the claimed ranges overlap or lie inside the ranges disclosed by the prior art and even when the claimed ranges and prior art ranges do not overlap but are close enough that one skilled in the art would have expected them to have similar properties, a prima facie case of obviousness exists. The courts have also found that 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.
Therefore, the claimed ranges merely represent an obvious variant and/or routine optimization of the values of the cited prior art.
Furthermore, Applicant is reminded that In re Best (195 USPQ 430) and In re Fitzgerald (205 USPQ 594) discuss the support of rejections wherein the prior art discloses subject matter which there is reason to believe includes functions that are newly cited or is identical to a product instantly claimed. In such a situation the burden is shifted to the applicants to “prove that subject matter shown to be in the prior art does not possess the characteristic relied on” In the present case, Applicant would need to show that claimed concentration ranges work exceptionally well for metal extractions compared to concentration values that deviate from claimed values, and demonstrate that Singer’s IL with -OR6 substitution on their R2-3 (such as their preferred embodiments 14a-e – disclosed herein) lack the property of the instantly claimed IL which allows for “highly effective separation of rare earth metals from other rare earth metals”
In addition, regarding the composition comprising two ILs, one with lower viscosity, the courts have found that “[i]t is prima facie obvious to combine two compositions each of which is taught by the prior art to be useful for the same purpose, in order to form a third composition to be used for the very same purpose.... [T]he idea of combining them flows logically from their having been individually taught in the prior art. It is therefore obvious to provide a mixture of the two agents in the absence of unexpected results.
Double Patenting
Applicant's arguments filed 12/15/2025 have been fully considered but they are not persuasive.
Applicant traverses the rejections, however, provides no specific arguments against rejections.
Claims stand rejected over the obviousness-type double patenting (ODP) rejections presented herein.
Conclusion
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). 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 JACKSON J HERNANDEZ whose telephone number is (571)272-5382. The examiner can normally be reached Mon - Thurs 7:30 to 5.
Examiner interviews are available via telephone and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Kortney L. Klinkel can be reached at (571) 270-5239. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/JACKSON J HERNANDEZ/Examiner, Art Unit 1627
/SARAH PIHONAK/Primary Examiner, Art Unit 1627