Prosecution Insights
Last updated: July 17, 2026
Application No. 18/264,127

PROCESSES FOR PURIFYING ORGANIC AMINES

Final Rejection §103
Filed
Aug 03, 2023
Priority
May 19, 2021 — nonprovisional of PCTCN2021094704
Examiner
SAWYER, JENNIFER C
Art Unit
1691
Tech Center
1600 — Biotechnology & Organic Chemistry
Assignee
Dow Chemical Korea Limited
OA Round
2 (Final)
69%
Grant Probability
Favorable
3-4
OA Rounds
0m
Est. Remaining
60%
With Interview

Examiner Intelligence

Grants 69% — above average
69%
Career Allowance Rate
384 granted / 559 resolved
+8.7% vs TC avg
Minimal -9% lift
Without
With
+-9.1%
Interview Lift
resolved cases with interview
Typical timeline
2y 9m
Avg Prosecution
49 currently pending
Career history
601
Total Applications
across all art units

Statute-Specific Performance

§101
0.3%
-39.7% vs TC avg
§103
68.9%
+28.9% vs TC avg
§102
8.4%
-31.6% vs TC avg
§112
8.9%
-31.1% vs TC avg
Black line = Tech Center average estimate • Based on career data from 559 resolved cases

Office Action

§103
Notice of Pre-AIA or AIA Status The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA . Detailed Action This office action is in response to applicant’s communication filed on 3/10/26. Claims 1-11 are pending in this application and are being examined in this Office Action. Due to applicant’s claim amendments and new claim filed 3/10/26, the objection and 112 rejection are withdrawn, and the previous 103 rejection has been modified, as shown below. Claim Rejections – 35 USC 103 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 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. 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 of this title, 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 1-11 are rejected under 35 U.S.C. 103 as being unpatentable over Sun et al. (CN 103102273, pub date 5/15/2013, in applicant’s IDS filed 8/3/23, the English translation is used herein), in view of Fang et al. (CN 109160876, pub date 1/8/2019, in applicant’s IDS filed 8/3/23, the English translation is used herein), further in view of Patil (Distillation Operations: Methods, Operational and Design Issues, Sep 2009, National Conference of Heat and Mass Transfer FAMT Ratnagiri). Determination of the Scope and Content of the Prior Art (MPEP §2141.01) Sun et al. teaches a method for purifying organic amine electroplating additives for semiconductor/electronic applications by removing cationic and anionic impurities from the organic amine additives using an electro-deionization device. Sun teaches that organic amine electroplating additives include triethanolamine, triisopropanolamine, diethylene glycolamine, triethylenediamine, N,N-diethylpropynylamine, tetramethylammonium hydroxide (TMAH), and related organic amines. Sun further teaches that these organic amine compounds may be used as electroplating additives in the semiconductor industry. (pages 5-6) Sun teaches that commercially available industrial-grade organic amine compounds contain metal ion impurities and anion impurities, making them unsuitable for use in electronic electroplating, especially in semiconductor wafer electroplating. Sun explains that metal ions such as Fe, Cu, and Na can contaminate IC chips, cause oxidation-induced stacking faults, increase leakage current, and reduce minority-carrier lifetime. Thus, Sun identifies the same problem addressed by the applicant: reducing metal ion contamination in organic amine compounds for electronic/semiconductor applications. (pages 5-7) Sun teaches that purification is performed using an electro-deionization device having purification chambers filled with ion exchange resin. Sun teaches that the anion exchange resin and cation exchange resin may be selected from styrene-based ion exchange resins, polyacrylic acid-based ion exchange resins, aminophosphonic acid chelating resins, and iminodiacetic acid chelating resins. Thus, Sun teaches resin materials corresponding to applicant’s AMPA and IDA resin functional groups. (pages 1-3, 8, 12) Sun teaches that the liquid flow rate of the purification chamber is 1-100 L/h, the flow rates of the concentrate chamber and electrode chamber are 1-100 L/h, the initial voltage is 0-100V, and the solution temperature is maintained at 20-70°C. Sun further teaches a preferred operating temperature of 45-60°C. Sun teaches sampling the output and collecting the purified organic amine electroplating additive once the impurity anion and cation concentrations meet the standard requirements of fine electronic grade. (pages 1-4, 9-10, 13-16) Sun teaches that the purified organic amine electroplating additive solution may be filtered through a 0.1-0.22 μm microfiltration membrane to obtain a final product. Sun also teaches that the method may further include dehydrating and concentrating the purified organic amine electroplating additive by vacuum distillation. (pages 4, 10, 14) Sun exemplifies purification of TMAH. In Example 1, industrial-grade TMAH is treated by EDI using ion exchange resins, and after 90 minutes, the resulting concentrations of anions and cations meet the SEMI standard. Sun reports that, after concentration conversion, all metal ion concentrations were below 2-10 ppb, chloride ion concentration was below 0.1 ppm, and carbonate ion concentration was below 100 ppm. Examples 2 and 3 similarly report purification to SEMI standard, with all metal ions below 2-10 ppb. (pages 14-16) With regard to new claim 11, Sun teaches passing TMAH solutions having concentrations up to 25%, preferably 2.38%-25%, through the resin-containing EDI purification device, and Sun’s Example 1 uses a 25% TMAH solution. Sun further teaches concentrating purified TMAH by vacuum distillation to remove water. Because Sun’s disclosed concentration range overlaps the claimed 20 wt% to 70 wt% range, and because concentration of the amine solution would have been an ordinary process variable affecting throughput and water-removal burden, the claimed concentration range would have been obvious absent evidence of criticality or unexpected results. Ascertainment of the Difference Between Scope the Prior Art and the Claims (MPEP §2141.012) Sun et al. is deficient in the sense that it does not teach applicant’s step (c) heating the amine to a sub-boiling temperature. However, Fang et al. teaches a method for preparing electronic-grade cyclohexanone by using reduced-pressure distillation, ion exchange resin adsorption, and sub-boiling distillation. Fang teaches that electronic-grade cyclohexanone is used for cleaning precision electronic components, and that the method is intended to provide electronic-grade material. (pages 1-3) Fang teaches, in step (1), reduced-pressure distillation of cyclohexanone to remove water, light components, heavy components, and other impurities. Fang teaches a bottom temperature of 80-105°C, a top temperature of 40-70°C, a condensate temperature of 2-15°C, and reduced pressure of 500-5000 Pa at the vessel bottom and 400-4500 Pa at the vessel top. (pages 1, 3-4) Fang teaches, in step (2), ion exchange resin adsorption after reduced-pressure distillation. Fang teaches that cyclohexanone is first adsorbed by an anion exchange resin and then by a cation exchange resin to remove most metal ions. Fang identifies D201 macroporous weakly basic styrene-based anion exchange resin and D113 macroporous weakly acidic acrylic-based cation exchange resin. (pages 1-4, 7-10) Fang teaches, in step (3), sub-boiling distillation. Fang teaches adding the resin-treated cyclohexanone to a sub-boiling still and heating the cyclohexanone to 145-150°C under high-purity argon to remove metal ions and obtain electronic-grade cyclohexanone having a content greater than 99.98% and individual metal ion contents less than or equal to 10 ppb. (pages 1-2, 3, 7-10) Fang expressly teaches the technical reason for sub-boiling distillation. Fang teaches that, because cyclohexanone does not reach its boiling point, the gas phase in equilibrium with the liquid phase is no longer composed of a large number of vapor particles. Fang teaches that this avoids entry of tiny droplets or aerosols carrying impurities into the gas phase, which would otherwise mix into the finished cyclohexanone during recondensation/collection and result in an impure finished product. (page 5) Fang further teaches that, unlike traditional bottom heating, the sub-boiling distillation apparatus places the heater a few centimeters above the liquid surface and heats the liquid surface by thermal radiation, making the liquid surface temperature higher than the temperature below, weakening mixing between liquid layers, and producing stable/static evaporation. Fang teaches that the evaporated cyclohexanone vapor is therefore almost free of tiny water droplets or aerosols containing impurities. (page 5) Fang teaches using high-purity argon during sub-boiling distillation to avoid contamination from air. Fang’s examples teach replacing the sub-boiling still with high-purity argon 4 to 6 times to remove air before heating, and then heating under high-purity argon to remove metal ions. (pages 5-10) Furthermore, Patil teaches general distillation principles. Patil teaches that vacuum operation should be considered for heat-sensitive compounds or polymerizable materials where a low bottom temperature is needed to avoid thermal decomposition. Patil also teaches that reboiler temperatures should be kept low enough to avoid bottoms degradation and/or fouling. (page 1) Patil teaches that a distillation unit includes a condenser to cool and condense the vapor leaving the top of the column, and that condensed liquid is stored in a reflux drum or removed as distillate/top product. (page 2) Patil teaches vacuum distillation as a distillation method operating at very low or near-vacuum pressure, which allows the mixture to boil at a lower temperature and thereby avoids thermal degradation problems. (page 3) Patil further teaches that entrainment refers to liquid carried by vapor upward, that entrainment is caused by high vapor flow rates, that entrainment reduces efficiency, and that entrainment can contaminate high-purity distillate. (page 8) he Additionally, with regard to amended claim 10, Fang teaches an electronic-grade product having moisture content ≤100 ppm, which is less than 1 wt% water. Sun also teaches that the purified organic amine electroplating additive may be dehydrated and concentrated by vacuum distillation, and specifically teaches concentrating TMAH by vacuum distillation to remove water when the TMAH concentration is below 25%. Patil further teaches vacuum distillation as a known lower-temperature distillation technique and teaches condensation of vapor to liquid distillate. Therefore, it would have been obvious to reduce water content in the purified organic amine to less than 1 wt% by applying known dehydration/concentration distillation steps in order to obtain an electronic-grade organic amine having low moisture content. Finding of Prima Facie Obviousness Rationale and Motivation (MPEP §2142-2143) Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to modify Sun’s electronic-grade organic amine purification process to include Fang’s sub-boiling distillation under inert gas as a downstream polishing step after Sun’s resin/EDI purification, in order to further reduce metal ion contamination while avoiding impurity-containing droplet or aerosol entrainment during purification. Sun and Fang are analogous and directed to the same general problem: preparing high-purity/electronic-grade organic chemicals by removing metal ion and other impurities. Sun teaches that organic amine additives such as triethanolamine and TMAH are used in semiconductor/electronic applications and must be purified from metal and anion impurities to meet fine electronic-grade standards. Fang teaches that electronic-grade organic chemicals can be prepared by combining ion exchange resin adsorption with sub-boiling distillation under high-purity argon, and that this sequence provides very low metal ion levels. Thus, a person of ordinary skill seeking to further improve Sun’s electronic-grade organic amine purification would have looked to Fang’s sub-boiling distillation as an additional purification/polishing step. The proposed modification does not replace Sun’s EDI device or destroy Sun’s intended purpose. Sun’s intended purpose is to remove metal ion and anion impurities from organic amine electroplating additives so that they meet fine electronic-grade standards. Adding Fang’s sub-boiling distillation after Sun’s resin/EDI purification would further that purpose. Additionally, Sun teaches that the method may further include dehydrating and concentrating the purified organic amine electroplating additive by vacuum distillation. Therefore, Sun does not teach away from downstream distillation of the purified organic amine; rather, Sun expressly contemplates a downstream distillation step. Fang provides a specific reason to use sub-boiling distillation rather than ordinary boiling distillation. Fang teaches that, when the material does not reach its boiling point, impurity-containing droplets or aerosols generated by boiling are prevented from entering the vapor phase and contaminating the recondensed finished product. Fang further teaches that the sub-boiling apparatus produces stable/static evaporation and vapor almost free of impurity-containing droplets or aerosols. Patil confirms that entrainment of liquid in vapor is a known distillation problem and can contaminate high-purity distillate. Thus, one of ordinary skill in the art would have had a reason to use Fang’s sub-boiling distillation to reduce metal ion contamination and avoid entrainment-related contamination in Sun’s electronic-grade organic amine product. Fang’s absolute sub-boiling temperature of 145-150°C is specific to cyclohexanone and is not being relied upon as the temperature that must be copied for triethanolamine or other organic amines. Instead, Fang is relied upon for its teaching of a sub-boiling relationship: heating the material being purified below its boiling point to avoid boiling-generated impurity-containing droplets or aerosols. A person of ordinary skill applying Fang’s teaching to Sun’s organic amine purification would have selected a sub-boiling temperature appropriate for the boiling point of the selected organic amine, including a temperature below the normal boiling point as claimed. Selection of the precise sub-boiling temperature would have been a routine matter of process optimization because Fang expressly identifies the below-boiling condition as affecting impurity entrainment and product purity. Patil further supports the selection of lower-temperature distillation conditions. Patil teaches that vacuum distillation allows boiling at a lower temperature to avoid thermal degradation, and that reboiler temperatures should be kept low enough to avoid degradation and fouling. Thus, one of ordinary skill would have understood the desirability of using lower-temperature distillation conditions for high-boiling or thermally sensitive organic chemicals. Patil also teaches the standard distillation step of cooling and condensing vapor to obtain liquid distillate, corresponding to the claimed cooling of vapor to obtain purified liquid organic amine. With respect to the claimed inert gas environment and oxygen content limitation, Fang teaches performing sub-boiling distillation under high-purity argon and replacing the sub-boiling still with high-purity argon 4 to 6 times to remove air before heating. Since air contains oxygen, replacing air with high-purity argon would reasonably be expected to reduce oxygen content in the sub-boiling environment and in the treated material. Fang also teaches that high-purity argon avoids contamination by air. Therefore, it would have been obvious to conduct the sub-boiling distillation under inert gas and to reduce oxygen content. With respect to applicant’s resin limitation, Sun expressly teaches using ion exchange resins including aminophosphonic acid chelating resins and iminodiacetic acid chelating resins in the purification chamber for purifying organic amine electroplating additives. Thus, Sun teaches the claimed IDA/AMPA chelating resin functional groups. Fang further supports combining resin treatment with sub-boiling distillation because Fang performs ion exchange resin adsorption before sub-boiling distillation in an electronic-grade purification process. With respect to applicant’s ordering limitations, Fang expressly teaches ion exchange resin adsorption followed by sub-boiling distillation. Thus, to the extent the claims require resin treatment before sub-boiling distillation, Fang directly teaches that order. To the extent the claims encompass a different order, the order of known purification steps would have been obvious absent evidence of criticality or unexpected results because both resin treatment and sub-boiling distillation were known impurity-reduction steps, and applicant has not shown that the broad claimed order produces an unexpected result commensurate in scope with the claims. With respect to applicant’s water content limitation, Fang teaches electronic-grade cyclohexanone having moisture content ≤100 ppm after the purification process. Sun also teaches optional downstream vacuum distillation for dehydrating and concentrating the purified organic amine electroplating additive. Therefore, controlling water content in an electronic-grade organic chemical purification process would have been an expected result of routine optimization of known dehydration/distillation conditions. With respect to applicant’s metal ion concentration limitations, Sun teaches purification of organic amine electroplating additives to fine electronic-grade standards and exemplifies TMAH having all metal ion concentrations below 2-10 ppb after EDI purification. Fang teaches ion exchange resin adsorption followed by sub-boiling distillation to obtain electronic-grade material having individual metal ion contents no greater than 10 ppb. Accordingly, the prior art provides a reasonable expectation that combining Sun’s organic amine resin/EDI purification with Fang’s sub-boiling distillation would produce very low metal ion levels in an electronic-grade organic amine product. With respect to applicant’s resin pore size and particle diameter limitations, Sun teaches the use of ion exchange/chelating resins for purification of organic amines, including aminophosphonic acid and iminodiacetic acid chelating resins. Pore size and particle diameter are ordinary physical properties of resin beads that affect contact area, liquid flow, pressure drop, and adsorption/ion-exchange performance. In the absence of evidence of criticality or unexpected results for the claimed pore size and particle diameter ranges, selecting conventional resin bead properties suitable for flow-through purification would have been obvious. However, the primary reliance for the resin chemistry remains Sun’s express teaching of AMPA and IDA chelating resins. Therefore, it would have been obvious to one of ordinary skill in the art to combine Sun’s organic amine electronic-grade purification process with Fang’s sub-boiling distillation under high-purity argon, with Patil evidencing the ordinary distillation principles of lower-temperature operation, condensation, and entrainment control, in order to obtain purified organic amines having reduced metal ion contamination suitable for electronic/semiconductor applications. Response to Arguments Applicant’s arguments have been considered but are not persuasive for the following reasons: The examiner acknowledges applicant’s arguments for the failure of the references to teach the limitations of claim 1. Applicant argues that the cited references do not teach or suggest multiple limitations of independent claim 1. The examiner does not agree with applicant’s arguments. Applicant’s arguments attack the references individually rather than addressing the combined teachings of Sun, Fang, and Patil. Sun teaches purification of organic amine electroplating additives for semiconductor/electronic applications. Sun identifies organic amine electroplating additives including triethanolamine, triisopropanolamine, diethylene glycolamine, triethylenediamine, N,N-diethylpropynylamine, and tetramethylammonium hydroxide. Sun further teaches that these organic amines are useful in semiconductor electroplating applications and that industrial-grade organic amines contain metal ion and anion impurities that make them unsuitable for semiconductor wafer electroplating. Sun expressly identifies the problem of metal contamination, including Fe, Cu, and Na contamination, in semiconductor IC chips. Sun also teaches purification chambers filled with ion exchange resin and identifies suitable resins as including styrene-based ion exchange resins, polyacrylic-acid-based ion exchange resins, aminophosphonic acid chelating resins, and iminodiacetic acid chelating resins. Thus, Sun teaches the organic amine purification context and the claimed IDA/AMPA-type resin chemistry. Fang teaches the missing sub-boiling distillation step. Fang teaches an electronic-grade organic chemical purification process that includes reduced-pressure distillation, ion exchange resin adsorption, and sub-boiling distillation under high-purity argon. Fang teaches that ion exchange resin adsorption removes most metal ions and that subsequent sub-boiling distillation further removes metal ions to obtain electronic-grade material having individual metal ion contents of no more than 10 ppb. Fang further teaches the technical reason for sub-boiling distillation: because the liquid does not reach its boiling point, impurity-containing droplets or aerosols generated by boiling do not enter the gas phase and contaminate the recondensed finished product. Fang also teaches that the sub-boiling apparatus produces stable/static evaporation and vapor almost free of impurity-containing droplets or aerosols. Patil confirms ordinary distillation principles, including that vapor leaving a distillation column is cooled and condensed to liquid distillate, and that entrainment of liquid in vapor can contaminate high-purity distillate. Accordingly, the references collectively teach or suggest organic amine purification, contact with IDA/AMPA-type chelating resin, inert-gas operation, sub-boiling heating, vapor formation, cooling/condensation of vapor, and reduction of metal impurities. The examiner acknowledges applicant’s arguments for the failure that the claimed parameters were recognized as result-effective variables. The examiner does not agree with applicant’s arguments. Fang expressly identifies the below-boiling condition as affecting product purity. Fang explains that when the material being purified does not reach its boiling point, impurity-containing droplets or aerosols generated by boiling are not carried into the gas phase and therefore do not contaminate the recondensed product. Thus, Fang recognizes the sub-boiling temperature relationship as result-effective for reducing impurity entrainment and improving purity. Fang also recognizes the inert-gas environment as purity-affecting. Fang teaches performing sub-boiling distillation under high-purity argon and explains that high-purity argon avoids contamination from air. Fang’s examples further teach replacing the sub-boiling still with high-purity argon 4 to 6 times to remove air before heating. Sun recognizes the resin chemistry as relevant to impurity removal. Sun teaches that the purification chamber is filled with ion exchange resin and expressly identifies aminophosphonic acid chelating resins and iminodiacetic acid chelating resins among the resins used for purifying organic amine electroplating additives. Therefore, the cited art recognizes the sub-boiling condition, inert-gas operation, and IDA/AMPA chelating resin selection as features affecting impurity removal and product purity. The examiner acknowledges applicant’s arguments for the unsuitability of modifying Sun with Fang. Applicant argues that the proposed modification would render Sun unsuitable for its intended purpose because Sun is an EDI system requiring an aqueous ion-conductive environment. The examiner does not agree with applicant’s arguments. The rejection does not propose replacing Sun’s EDI operation with Fang’s sub-boiling distillation. Rather, Fang’s sub-boiling distillation is used as an additional downstream polishing step after Sun’s resin/EDI purification. Sun’s intended purpose is to remove metal ion and anion impurities from organic amine electroplating additives so that the additives meet fine electronic-grade standards. Adding Fang’s sub-boiling distillation would further that same purpose by further reducing metal ion contamination and avoiding impurity-containing aerosol or droplet entrainment during distillation. Additionally, Sun itself contemplates a downstream distillation step. Sun teaches that the method may further include dehydrating and concentrating the purified organic amine electroplating additive by vacuum distillation. Thus, Sun does not teach away from downstream distillation of the purified organic amine product. To the contrary, Sun expressly allows post-purification vacuum distillation. Applicant’s argument assumes that the EDI process would be replaced or destroyed, but that is not the proposed combination. Fang also teaches the compatibility of resin-based purification and subsequent sub-boiling distillation. Fang performs ion exchange resin adsorption and then sub-boiling distillation in sequence to prepare an electronic-grade organic chemical. Therefore, the proposed combination would not render Sun unsuitable for its intended purpose, but would further Sun’s goal of producing an electronic-grade purified organic amine. The examiner acknowledges applicant’s arguments for the inapplicability of Fang’s ketone-specific conditions to organic amines. Applicant argues that Fang’s cyclohexanone-specific conditions cannot reasonably be applied to organic amines. The examiner does not agree with applicant’s arguments. Applicant’s argument is not persuasive because the rejection does not rely on directly copying Fang’s absolute cyclohexanone temperature to triethanolamine or any other organic amine. Fang is relied upon for its broader sub-boiling purification teaching: heating the material being purified below its boiling point under inert gas to avoid boiling-generated impurity-containing droplets or aerosols that would otherwise enter the vapor phase and contaminate the recondensed product. This rationale is not limited to ketones; it concerns the general distillation problem of impurity entrainment in vapor and contamination of condensed high-purity product. Sun supplies the amine-specific motivation. Sun teaches that organic amine electroplating additives, including triethanolamine and TMAH, are used in semiconductor applications and require removal of metal ion and anion impurities to meet fine electronic-grade standards. Patil further confirms that entrainment is a known distillation problem and can contaminate high-purity distillate. Thus, a person of ordinary skill applying Fang’s sub-boiling purification principle to Sun’s organic amine purification process would have selected a sub-boiling temperature appropriate for the boiling point of the selected organic amine, rather than copying Fang’s absolute cyclohexanone temperature. The examiner acknowledges applicant’s arguments for the insufficiency of Patil. Applicant argues that Patil provides no guidance on the suitability of amines for reduced-pressure distillation. The examiner does not agree with applicant’s arguments. Patil is not relied upon as the amine-specific purification reference. Sun provides the amine-specific teaching. Sun teaches purification of organic amine electroplating additives, including triethanolamine and TMAH-type amines, for semiconductor/electronic applications. Fang provides the sub-boiling electronic-grade purification teaching. Patil is relied upon only for ordinary distillation knowledge, including that vacuum operation allows distillation at lower temperature to avoid thermal degradation, that reboiler temperatures should be kept low enough to avoid degradation or fouling, that vapor is cooled and condensed to liquid distillate, and that entrainment can contaminate high-purity distillate. Thus, Patil is properly used as evidence of general knowledge in distillation practice and to support the reasonableness of using lower-temperature distillation and entrainment control in combination with Sun and Fang. Patil need not independently teach organic amine purification because that teaching is provided by Sun. The examiner acknowledges applicant’s arguments for unexpected results. Applicant argues that the specification demonstrates unexpected results because resin treatment alone and sub-boiling distillation alone do not achieve the same metal-removal performance as the claimed combination. The examiner does not agree with applicant’s arguments or unexpected results. Fang already teaches the same general type of combined purification sequence: ion exchange resin adsorption followed by sub-boiling distillation under high-purity argon. Fang reports that this combination provides electronic-grade material having individual metal ion contents of no more than 10 ppb. Sun also teaches purification of organic amine electroplating additives to fine electronic-grade standards using ion exchange/chelating resin in an EDI process and reports metal ion concentrations below 2-10 ppb in purified TMAH. Thus, the cited art provides a reasonable expectation that combining resin-based organic amine purification with sub-boiling distillation would further reduce metal ion contamination. Applicant’s evidence that each step alone may be less effective than the combination does not necessarily establish unexpected results over the combined teachings of Sun and Fang, because Fang already teaches using ion exchange resin adsorption together with sub-boiling distillation for electronic-grade purification. Further, applicant’s unexpected results are not commensurate in scope with the claims, which encompass broad classes of organic amines, multiple resin matrices, and both IDA and AMPA resin chemistry. Applicant has not established that the alleged unexpected results occur across the full scope of the claims. For these reasons, applicant’s arguments do not overcome the prima facie case of obviousness. Conclusion Claims 1-11 are rejected. 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 extension fee 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 date of this final action. Any inquiry concerning this communication or earlier communications from the examiner should be directed to Jennifer Cho Sawyer whose telephone number is (571) 270 1690. The examiner can normally be reached on Monday-Friday 9 AM - 6 PM PST. If attempts to reach the examiner by telephone are unsuccessful, the examiner's supervisor, Renee Claytor can be reached on (571) 272-8394. The fax phone number for the organization where this application or proceeding is assigned is 571-274-1690. Information regarding the status of an application may be obtained from the Patent Application Information Retrieval (PAIR) system. Status information for published applications may be obtained from either Private PAIR or Public PAIR. Status information for unpublished applications is available through Private PAIR only. For more information about the PAIR system, see http://pair-direct.uspto.gov. Should you have questions on access to the Private PAIR system, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative or access to the automated information system, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000. Jennifer Cho Sawyer Patent Examiner Art Unit: 1691 /RENEE CLAYTOR/Supervisory Patent Examiner, Art Unit 1691
Read full office action

Prosecution Timeline

Aug 03, 2023
Application Filed
Dec 22, 2025
Non-Final Rejection mailed — §103
Mar 10, 2026
Response Filed
Jun 04, 2026
Final Rejection mailed — §103 (current)

Precedent Cases

Applications granted by this same examiner with similar technology

Patent 12668562
MOLECULAR TETRAHEDRON NANOCAGE, ITS PREPARATION, AND USES THEREOF
3y 7m to grant Granted Jun 30, 2026
Patent 12668569
SYNTHESIS OF PROSTATE SPECIFIC MEMBRANE ANTIGEN (PSMA) LIGANDS
3y 1m to grant Granted Jun 30, 2026
Patent 12655092
PRECURSOR COMPOUNDS OF ESTER COMPOUNDS
4y 6m to grant Granted Jun 16, 2026
Patent 12643850
PREPARATION OF AROMATIC CARBOXYAMIDES BY PALLADIUM-CATALYZED CARBONYLATION REACTION
3y 7m to grant Granted Jun 02, 2026
Patent 12637409
STYRYL CARBOXYLATE DERIVATIVES
2y 0m to grant Granted May 26, 2026
Study what changed to get past this examiner. Based on 5 most recent grants.

Strategy Recommendation AI-generated — please review before filing

Get a prosecution strategy drawn from examiner precedents, rejection analysis, and claim mapping.
Typically takes 5-10 seconds — AI-generated, attorney review required before filing

Prosecution Projections

3-4
Expected OA Rounds
69%
Grant Probability
60%
With Interview (-9.1%)
2y 9m (~0m remaining)
Median Time to Grant
Moderate
PTA Risk
Based on 559 resolved cases by this examiner. Grant probability derived from career allowance rate.

Sign in with your work email

Enter your email to receive a magic link. No password needed.

Personal email addresses (Gmail, Yahoo, etc.) are not accepted.

Free tier: 3 strategy analyses per month