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 .
Change in Examiner
Please note the Examiner for this Application has changed.
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 09/25/2025 has been entered.
Information Disclosure Statement
The information disclosure statement (IDS) submitted on 09/25/2025 is in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statement is being considered by the examiner.
Claim Rejections - 35 USC § 102, Anticipation
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claims 1 and 4-6 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Chen (CN 103788284; Date of Publication: May 14, 2014 – previously cited).
Chen's general disclosure relates to an ionic liquid with high elongation rates and an adjustable elastic modulus (see, e.g., Chen, abstract).
Regarding claim 1 pertaining to a composition comprising at least one cation and at least one anion, Chen teaches a composition comprising alpha-ketoglutaric acid, which is the anion, and imidazolium, which is the cation (see, e.g., Chen, pg. 2, "Summary of the Invention", paragraphs 5-6 & Example 4 & Claim 5).
Regarding claims 4-5 pertaining to the anion, Chen teaches a composition comprising alpha-ketoglutaric acid, which is an anion (see, e.g., Chen, pg. 2, "Summary of the Invention", paragraphs 5-6 & Example 4 & Claim 5).
Regarding claim 6 pertaining to the cation, Chen teaches a composition comprising an imidazolium cation, wherein the imidazolium cation is 1-ethyl-3-methylimidazole, 1-methyl-3-methylimidazole, 1-butyl-3-methylimidazole, or 1-butyl-3-methylimidazole (see, e.g., Chen, pg. 2, "Summary of the Invention", paragraph 6).
Examiner’s Response to Arguments
Applicant's arguments filed 09/25/2025 have been fully considered but they are not persuasive.
Regarding Applicant’s arguments that Chen lacks description of an ionic liquid comprising at least one anion (remarks, page 4), this argument is not persuasive because, as discussed above, Chen teaches a composition comprising alpha-ketoglutaric acid, which is inherently an anion (see, e.g., Chen, pg. 2, "Summary of the Invention", paragraphs 5-6 & Example 4 & Claim 5). Furthermore, the instant specification states “Examples of ketoacids for use in the ionic liquids and methods of the invention include, but are not limited to, a-ketoglutaric acid, pyruvic acid, acetoacetic acid, levulinic acid, and the like” (see, e.g., instant specification, [0048]). Furthermore, the instantly claimed invention recites that alpha-ketoglutaric acid is an anion (see, e.g., instantly claimed invention, claims 4-5).
Regarding Applicant’s arguments that Chen uses alpha-ketoglutarate as a photoinitator (remarks, page 5), this argument is not persuasive because, as discussed above, alpha-ketoglutaric acid, which is inherently an anion (see, e.g., Chen, pg. 2, "Summary of the Invention", paragraphs 5-6 & Example 4 & Claim 5). Therefore, Chen could have used it as a photoinitator, but it is still inherently an anion, which is also evidenced by the instant specification and instantly claimed invention.
Regarding Applicant’s arguments that there is no evidence that the photoinitators become electrostatically bound to the imidazolium cations in Chen (remarks, pages 5-6), this argument is not persuasive because the instantly claimed invention does not pertain to the electrostatic interaction between the alpha-ketoglutarate as a photoinitator and the imidazolium cation. Instead, the instantly claimed invention broadly claims a composition comprising at least one cation and at least one anion selected from the group consisting of mucic acid, saccharic acid, xylaric acid, arabinaric acid, mannaric acid, and ketoacid. As discussed above, and reiterated here, Chen teaches a composition comprising alpha-ketoglutaric acid, which is the anion, and imidazolium, which is the cation (see, e.g., Chen, pg. 2, "Summary of the Invention", paragraphs 5-6 & Example 4 & Claim 5). Therefore, Chen anticipates the instantly claimed invention because Chen teaches an imidazolium cation and an alpha-ketoglutaric acid anion. Moreover, the instantly claimed invention does not claim electrostatic interactions between the cation and anion.
Regarding Applicant’s arguments that Chen’s procedure cannot displace the anion with a photoinitator and that the procedure transforms catalytic photoinitatiors into other radical species (remarks, pages 6-7), this argument is not persuasive because, as discussed above and reiterated here, Applicant is broadly claiming a composition comprising at least one cation and at least one anion selected from the group consisting of mucic acid, saccharic acid, xylaric acid, arabinaric acid, mannaric acid, and ketoacid. Chen teaches a composition comprising alpha-ketoglutaric acid, which is the anion, and imidazolium, which is the cation (see, e.g., Chen, pg. 2, "Summary of the Invention", paragraphs 5-6 & Example 4 & Claim 5). Applicant provides no evidence or support that the alpha-ketoglutaric acid anion and imidazolium cation, as taught by Chen, are not anions and cation in ionic liquids. Moreover, Applicant is arguing the procedure taught by Chen, but not the actual composition taught by Chen, which comprises an ionic liquid comprising an alpha-ketoglutaric acid anion and imidazolium cation, which reads upon the instantly claimed invention.
Claim Rejections - 35 USC § 103, Obviousness
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claims 3 and 7-8 are rejected under 35 U.S.C. 103 as being unpatentable over Chen as applied to claims 1-2 and 4-6 above, and further in view of Larson (US 2015/0071925; Date of Publication: March 12, 2013 – previously cited).
The teachings of Chen are discussed above.
Regarding claim 8 pertaining to a composition comprising at least one cation and at least one anion, Chen teaches a composition comprising at least one cation and at least one anion, Chen teaches a composition comprising alpha-ketoglutaric acid, which is the anion, and imidazolium, which is the cation (see, e.g., Chen, pg. 2, "Summary of the Invention", paragraphs 5-6 & Example 4 & Claim 5).
However, Chen does not teach: wherein the anion is selected from the group consisting of a mucic acid anion, a saccharic acid anion, a xylaric acid anion, an arabinaric acid anion, and a mannaric acid anion (claim 3); or wherein the cation is choline (claim 7); or an ionic liquid comprising at least one anion and at least one cation, wherein the anion is selected from the group consisting of a mucic acid anion, a saccharic acid anion, a xylaric acid anion, an arabinaric acid anion, a mannaric acid anion, and a ketoacid anion, wherein if the anion is a mucic acid or if the anion is a ketoacid anion, wherein the ketoacid anion is a pyruvic acid anion, then the cation is not choline, and wherein if the anion is a keto acid anion, wherein the ketoacid anion is an a-ketoglutaric acid anion, then the cation is not a (C1-10 alkyl)z imidazolium (claim 8).
Larson's general disclosure relates to liquid pharmaceutical formulations for proteins containing ionic liquids (see, e.g., Larson, abstract & [0001]).
Regarding claim 3 pertaining to the anion, Larson teaches a composition comprising mucic acid (see, e.g., Larson, [0081]).
Regarding claim 7 pertaining to the cation, Larson teaches a composition comprising choline (see, e.g., Larson, [0287]).
Regarding claim 8 pertaining to the ionic liquid composition, Larson teaches ionic liquids are salt, zwitterion, or mixtures thereof that is a liquid at or near temperatures where most conventional salts are solids (see, e.g., Larson, [0082]). Moreover, Larson teaches that salts can include gluconic acid and mucic acid (see, e.g., Larson, [0081]), and Larson teaches choline and imidazolium as an organic base (see, e.g., Larson, [0297]). Therefore, Larson teaches a composition comprising mucic acid as an anion and imidazolium as a cation.
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to produce an ionic liquid comprising alpha-ketoglutaric acid and an imidazolium, as taught by Chen, wherein the alpha-ketoglutaric acid and the imidazolium are substituted for mucic acid and choline, respectively, as taught by Larson. One would have been motivated to do so because alpha-keto glutaric acid, as taught by Chen, and mucic acid, as taught by Larson, are both anions and functional equivalents that can both be used in ionic liquids. Moreover, imidazolium, as taught by Chen, and choline, as taught by Larson, are both cations and functional equivalents that can both be used in ionic liquids. Therefore, based on the teachings of Chen and Larson, it would have been obvious to produce an ionic liquid comprising a cation, such as imidazolium or choline, and an anion comprising alpha-ketoglutaric acid or mucic acid. One would have expected success because Chen and Larson both teach ionic liquid compositions.
Examiner’s Response to Arguments
Applicant's arguments filed 09/25/2025 have been fully considered but they are not persuasive.
Regarding Applicant’s arguments that Larson does not teach gluconic acids and that the ionic liquid can be formed from mucic or gluconic acid (remarks, pages 8-9), this argument is not persuasive because Larson teaches that salts can include gluconic acid and mucic acid (see, e.g., Larson, [0081]), which are inherently anions, as evidence by instant claims 1-2 5, and 8. Applicant does not provide evidence that mucic or gluconic acid are not anions, and actually claims these anions as part of an ionic liquid composition; therefore, Applicant’s arguments that there is technical unpredictability and no reasonable expectation of success with these anions is not persuasive since Larson teaches an ionic liquid composition comprising mucic and gluconic acid.
Regarding Applicant’s arguments pertaining to Dhepe (remarks, page 10), Dhepe was not relied upon in the above presented rejection; therefore, Applicant’s arguments are moot.
Conclusion
Claims 1-8 are rejected.
No claims are allowed.
Correspondence Information
Any inquiry concerning this communication or earlier communications from the examiner should be directed to NATALIE IANNUZO whose telephone number is (703)756-5559. The examiner can normally be reached Mon - Fri: 8:30-6:00 EST.
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/NATALIE IANNUZO/Examiner, Art Unit 1653
/SHARMILA G LANDAU/Supervisory Patent Examiner, Art Unit 1653
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