CTNF 18/548,990 CTNF 90074 DETAILED ACTION Notice of Pre-AIA or AIA Status 07-03-aia AIA 15-10-aia 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 The preliminary amendment filed on 09/05/2023 has been entered. Claims 4-7 and 9-10 have been amended. Thus claims 1-10 are currently pending and are under examination. Specification In the specification dated 09/05/2023, the "single view” drawing is referred to as "Fig. 1”. In accordance to 37 CFR 1.84(u)(1), please amend the specification throughout to refer to “the Figure.” Drawings 06-21 AIA New corrected drawings in compliance with 37 CFR 1.121(d) are required in this application because 37 CFR 1.84(u)(1) indicates that if a single drawing is filed, the drawing must not be numbered and the abbreviation "Fig." must not appear . Applicant is advised to employ the services of a competent patent draftsperson outside the Office, as the U.S. Patent and Trademark Office no longer prepares new drawings. The corrected drawings are required in reply to the Office action to avoid abandonment of the application. The requirement for corrected drawings will not be held in abeyance. 06-27 AIA In addition to Replacement Sheets containing the corrected drawing figure(s), applicant is required to submit a marked-up copy of each Replacement Sheet including annotations indicating the changes made to the previous version. The marked-up copy must be clearly labeled as “Annotated Sheets” and must be presented in the amendment or remarks section that explains the change(s) to the drawings. See 37 CFR 1.121(d)(1). Failure to timely submit the proposed drawing and marked-up copy will result in the abandonment of the application. Claim Objections Claim 6 is objected to because of the following informalities: a period sign is missing at the end of the claim. Claim Rejections - 35 USC § 112 07-30-02 AIA 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. 07-34-01 Claims 7-10 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention. Claims 7 and 9-10 recite the limitations "the weak-acid cationic exchange resin" and “the weak-base anionic ion exchange resin”. There is insufficient antecedent basis for these limitations in the claims. Claim 8 is also rendered indefinite for depending on claim 7. Regarding claim 8, the parenthetical limitation "methacrylic" renders the claim indefinite because it is unclear whether the limitation is part of the claimed invention. See MPEP § 2173.05(d). Regarding claims 7-8, the term “type” in the limitation “macroreticular type resins” renders the claims vague and indefinite because the term does not limit the claims to the recited species and thus is unclear as to how much variation of the recited species are tolerated by the use of term “type”. Claim Rejections - 35 USC § 103 07-06 AIA 15-10-15 In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status. 07-20-aia AIA 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. 07-23-aia AIA 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. 07-20-02-aia AIA 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. 07-21-aia AIA Claim s 1-5 are rejected under 35 U.S.C. 103 as being unpatentable over International publication WO2022091605A1 (WO’605, effectively filed Oct. 27, 2020) in view of Patent number CN104610061A (CN’061, cited in IDS 09/05/2023 ). Note the paragraph citations of these references are based on the machine translations (see the attached documents) . WO’605 teaches a method for purifying organic solvents from metal impurities. The reference discusses that the purified organic solvent obtained by the organic solvent purification method include dilution solvents, dissolving solvents, cleaning solvents, and drying solvents in semiconductor manufacturing processes ([0104]). Regarding claims 1 and 3, WO’605 exemplifies purification of propylene glycol monomethyl ether (PGME), specie of the claimed formula, wherein R 1 methyl, R 2 is H, R 3 is methyl, R 4 is hydrogen, and n is 1. PNG media_image1.png 139 267 media_image1.png Greyscale PGME structure The process is carried out by contacting PGME with a mixed bed of ion exchange resins comprising cationic ion exchange resins and anionic ion exchange resins in a column (second vessel) (step e) followed by performing a distillation step ([0014], [0018]-[0023] and [0107]). The reference further teaches that when using organic solvents that may undergo decomposition or denaturation due to heat, it is desirable to use a non-boiling distillation apparatus (first vessel) and perform distillation slowly at a low temperature of 70° C, which is 50° C below the boiling point of PGME (b.pt. 120° C) to obtain the treated solvent ([0097] and [0108]) (steps a and c). The reference, even though silent about step (d) of cooling the vapor to provide the liquid, a skilled artisan would understand that distillation apparatus is paired with a condenser to cool, condense and collect the separated vapor in liquid form. Regarding claim 2, while step (e) is conducted prior to steps (a)-(d) in WO’265, the reference fails to teach performing (c) and (d) prior to step (e), wherein the glycol ether in step (e) is in the liquid form step (d). However, reversing the order of the steps would not have changed the outcome of the final PGME (organic solvent) product. WO’265 discusses that contacting the organic solvent with an ion exchange resin followed by a distillation step, improved the removal efficiency of metal impurities and water that could not be removed by the ion exchange resin alone ([0013]-[0014]). As such, reversing the purification steps, i.e. first sub-boiling distillation that would separate the PGME solvent in vapor form and condense the vapor to liquid form followed by contacting the liquid PGME with the ion exchange resin, would yield nothing more than the expected purified PGME liquid. See MPEP § 2144.04. Regarding claim 4, WO’605 teaches that after the process steps, the concentration of Li, Na, Mg, Al, K, Ca, Ti, V, Cr, Mn, Fe, Ni, Cu, Zn, Ag, Ba and Pb in PGME are each <1 ng/L (<1 ppb) (Table 1, Example 1). Regarding claim 1 step (b), WO’605 fails to teach filling the first vessel with an inert gas prior to conducting non-boiling distillation. The deficiency is however cured by CN’061. In the same field of endeavor, CN’061 teaches a method for purifying ethyl lactate to obtain electronic grade ethyl lactate with reduced metal content. To achieve the objective, the purification process comprises passing ethyl lactate through ion exchange resin comprising anion and cation exchange resins ([0009]) and distilling the ethyl lactate by sub-boiling distillation in a sub-boiling still and heating to 5-10 °C below the boiling point under the protection of high-purity nitrogen to remove metal ions, thereby obtaining electronic grade ethyl lactate with a content greater than 99.99% and a metal ion content of less than 1 ppb ([0011]). The reference discusses that carrying out sub-boiling distillation under the protection of high-purity nitrogen not only avoids contamination from impurities in the air, but also increases the flow of high-purity nitrogen and improves distillation efficiency ([0020]). Accordingly, a skilled artisan would have been motivated in using the high-purity nitrogen taught by CN’061 in the non-boiling distillation of WO’605 with a reasonable expectation of success in avoiding contamination of PGME from impurities in the air and in improving distillation efficiency. Regarding claim 5, the reference teaches that by performing an ion exchange treatment step in which the organic solvent to be treated is brought into contact with an ion exchange resin, and then performing a distillation step in which the treated solution from the ion exchange treatment step is distilled, the removal efficiency of ionic metal impurities is improved, and it also becomes possible to remove metal fine particles and water that could not be removed by the ion exchange resin alone ([0014], [0024] and [0098]). Thus, the claimed amount of water would have been achieved in the first vessel. Furthermore, the oxygen content in the first vessel of less than 20 ppm would also have been achieved by the combination of WO’605 and CN’061 in which using a high-purity nitrogen taught by CN’061 during the non-boiling distillation in the distillation apparatus (first vessel) of WO’605 would avoid contamination from impurities in the air (such as oxygen). It would thus have been prima facie obvious to a skilled artisan before the effective filing date of the instant invention to conduct a process for purifying glycol ethers, the process comprising: (a) providing a glycol ether to a first vessel, the glycol ether having a normal boiling point at one bar and the glycol ether having the claimed formula of R 1 -O-(CHR 2 CHR 3 )O) n R 4 ; wherein R 1 is an alkyl group having 1 to 9 carbon atoms or a phenyl group; wherein R 2 and R 3 each individually is hydrogen, a methyl group or an ethyl group, provided that when R 3 is a methyl group or an ethyl group, R 2 is hydrogen and provided that when R 2 is a methyl group or an ethyl group, R 3 is hydrogen; wherein R 4 is hydrogen, an alkyl group having 1 to 4 carbon atoms, an acetyl group, or a propionyl group; and wherein n is an integer of 1 to 3; (b) filling the first vessel with inert gas; (c) heating the glycol ether in the first vessel to a sub-boiling temperature, wherein the sub-boiling temperature is at least 15° C. less than the normal boiling point; (d) cooling the vapor from the first vessel in a second vessel to provide a liquid; and (e) contacting the glycol ether with a mixed bed of ion exchange resins comprising cationic ion exchange resins and anionic ion exchange resins in view of the teachings of WO’265 and CN’061 . 07-22-aia AIA Claim s 6-10 are rejected under 35 U.S.C. 103 as being unpatentable over International publication WO2022091605A1 (WO’605, effectively filed Oct. 27, 2020) in view of Patent number CN104610061A (CN’061, cited in IDS 09/05/2023 ) as applied to claim s 1-5 above, and further in view of International publication WO2021000318A1 (WO’318) . Regarding claims 6 and 10, WO’605 further teaches the anionic ion exchange resins are weak-base anionic ion exchange resins that include weakly basic anion exchangers include tertiary amino groups, secondary amino groups, primary amino groups, and polyamine groups ([0031] and [0043]-[0044]). Regarding claims 6-9, the reference teaches the use of H-type strongly acidic cation exchanger resin ([0017]) but fails to teach the use of weak-acid cationic exchange resins as instantly claimed. The deficiency is however cured by WO’318. Regarding claim 6, WO’318 is directed to a process for purifying ( 1) a hydrophilic organic solvent, (2) a hydrolysable organic solvent, or (3) a mixture of a hydrophilic organic solvent and a hydrolysable organic solvent by treating the solvent(s) using an ion-exchange resin, where the hydrophilic organic solvents include but are not limited to propylene glycol methyl ether, dipropylene glycol methyl ether, tripropylene glycol methyl ether, propylene glycol ethyl ether, propylene glycol propyl ether, ethylene glycol propyl ether, ethylene glycol butyl ether, diethylene glycol methyl ether, diethylene glycol ethyl ether, diethylene glycol propyl ether, diethylene glycol butyl ether, ethanol, isopropanol, and the like; and mixtures thereof (species of the claimed formula) (pages 2-3). The process uses a mixed bed of ion exchange resin 1) a cationic ion exchange resin and (2) an anionic ion exchange resin. The cationic ion exchange resin used in the mixed bed of ion exchange resin is a weak-acid cationic ion exchange resin and the anionic ion exchange resin used in the mixed bed of ion exchange resin is a weak-base anionic ion exchange resin (page 5). Regarding claim 7, the weak-acid cationic ion exchange resin in WO’318 is a macroreticular type resin and the weak-base anionic ion exchange resin is a macroreticular type resin selected from the group consisting of a crosslinked styrene-divinyl benzene copolymer, a crosslinked acrylic acid-divinyl benzene copolymer, or a mixture thereof (page 6). Regarding claim 9, WO’318 further teaches that the weak-acid functionality of the weak-acid cationic ion exchange resins is selected from the group consisting of weak-acid carboxylic acid groups, weak-acid phosphonic acid groups, weak-acid phenolic groups, and mixtures thereof (page 7). WO’318 teaches that the use of a mixed bed of a weak-acid a cationic ion exchange resin and a weak-base anionic ion exchange resin obtains ultrapure hydrophilic organic solvent in which the metal content has been reduced to less than 100 ppt (page 4), whereas the mixed bed ion exchange resin of WO’605 reduces the metal ions to less than 1 ppb each (less than 1,000 ppt), which is higher than the one obtained in WO’318. Accordingly, a skilled artisan would have been motivated in using the mixed bed of a weak-acid a cationic ion exchange resin and a weak-base anionic ion exchange resin of WO’318 in the process of WO’605 with a reasonable expectation of success in obtaining ultrapure organic solvent such as PGME with a metal content of less than 100 ppt. It would thus have been prima facie obvious to a skilled artisan before the effective filing date of the instant invention to conduct a process for purifying glycol ethers, the process comprising: (a) providing a glycol ether to a first vessel, the glycol ether having a normal boiling point at one bar and the glycol ether having the claimed formula of R 1 -O-(CHR 2 CHR 3 )O) n R 4 ; wherein R 1 is an alkyl group having 1 to 9 carbon atoms or a phenyl group; wherein R 2 and R 3 each individually is hydrogen, a methyl group or an ethyl group, provided that when R 3 is a methyl group or an ethyl group, R 2 is hydrogen and provided that when R 2 is a methyl group or an ethyl group, R 3 is hydrogen; wherein R 4 is hydrogen, an alkyl group having 1 to 4 carbon atoms, an acetyl group, or a propionyl group; and wherein n is an integer of 1 to 3; (b) filling the first vessel with inert gas; (c) heating the glycol ether in the first vessel to a sub-boiling temperature, wherein the sub-boiling temperature is at least 15° C. less than the normal boiling point; (d) cooling the vapor from the first vessel in a second vessel to provide a liquid; and (e) contacting the glycol ether with a mixed bed of ion exchange resins comprising cationic ion exchange resins and anionic ion exchange resins, wherein the cationic ion exchange resins are weak-acid cationic ion exchange resins and wherein the anionic ion exchange resins are weak-base anionic ion exchange resins in view of the teachings of WO’265, CN’061 and WO’318 . Conclusion 12-151-07 AIA 07-97 12-51-07 Claim s 1-10 are rejected and no claims are allowed. Any inquiry concerning this communication or earlier communications from the examiner should be directed to MEDHANIT W BAHTA whose telephone number is (571)270-7658. The examiner can normally be reached Monday-Friday 8am-5pm. Examiner interviews are available via telephone, in-person, 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, Scarlett Goon can be reached at 571-270-5241. 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. /MEDHANIT W BAHTA/ Primary Examiner, Art Unit 1692 Application/Control Number: 18/548,990 Page 2 Art Unit: 1692 Application/Control Number: 18/548,990 Page 3 Art Unit: 1692 Application/Control Number: 18/548,990 Page 4 Art Unit: 1692 Application/Control Number: 18/548,990 Page 5 Art Unit: 1692 Application/Control Number: 18/548,990 Page 6 Art Unit: 1692 Application/Control Number: 18/548,990 Page 7 Art Unit: 1692 Application/Control Number: 18/548,990 Page 8 Art Unit: 1692 Application/Control Number: 18/548,990 Page 9 Art Unit: 1692 Application/Control Number: 18/548,990 Page 10 Art Unit: 1692 Application/Control Number: 18/548,990 Page 11 Art Unit: 1692 Application/Control Number: 18/548,990 Page 12 Art Unit: 1692 Application/Control Number: 18/548,990 Page 13 Art Unit: 1692
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