CTFR 18/017,700 CTFR 82947 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. Detailed Action This office action is in response to applicant’s communication filed on 1/27/26. Claims 1-10 are pending in this application. Claims 9-10 have been withdrawn. Claims 1-8 are being examined in this Office Action. Due to applicant’s claim amendments filed 1/27/26, the objection filed 11/6/25 have been withdrawn. Claim Rejections – 35 USC 112.2 07-30-02 The following is a quotation of the second paragraph of 35 U.S.C. 112: 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 Claim s 1-8 remains rejected under 35 U.S.C. 112, second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which applicant regards as the invention. Claim 1 is indefinite because of the claim language “a low-boiling-point compound”. The specification doesn’t define the metes and bounds of what compound would encompass a “low-boiling-point”, such that one would know what is included and what is excluded. Claim 3 is indefinite because of Formula (I), which give a formula of “R 2 N(CH 3 )”, described as a “dialkylmethylamine”. The examiner believes this in incorrect since the amination reaction is between dimethylamine and an alcohol or aldehyde (see claim 1). The product from this reaction would be the following tertiary amine: dimethylalkylamine, corresponding to RN(CH 3 ) 2 . The dependent claims are rejected as being dependent on a rejected claim. Appropriate correction is required. 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 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 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. 07-23 AIA The factual inquiries set forth in Graham v. John Deere Co., 383 U.S. 1, 148 USPQ 459 (1966), that are applied for establishing a background for determining obviousness under 35 U.S.C. 1 03(a) are summarized as follows: Applicant Claims Determining the scope and contents of the prior art. Ascertaining the differences between the prior art and the claims at issue, and resolving the level of ordinary skill in the pertinent art. 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 Claim s 1-8 remain rejected under 35 U.S.C. 103(a) as being unpatentable over Abe et al. (US 5266730, pub date Nov. 30, 1993, in view of Armarego et al. (Purification of Laboratory Chemicals, Elsevier Inc., 2009, 6 th Ed. ISBN: 978-1-85617-567-8) . Determination of the Scope and Content of the Prior Art (MPEP §2141.01) Abe et al. teaches the reaction of dimethylamine with alcohols and aldehydes and a copper catalyst, containing also a fourth period transition metal. The copper metal in the catalyst reads on applicant’s “main active component” limitation for the metal catalyst in claim 8. Abe et al. exemplifies the reaction of lauryl alcohol (which contains 12 carbons) with dimethylamine and a catalyst containing copper, with hydrogen gas in Example 1, Table 1 and Examples 33, 23 and 24, Table 18. Abe et al. also exemplifies the reaction of lauraldehyde (which contains 12 carbons) with dimethylamine in Example 65, Table 33. In the “Note” “a 4 ” section of Table 6, column 17, Able et al. shows that the amination reaction of lauraldehyde and dimethylamine gives the product, “lauryldimethyl tertiary amine”, which is also known as lauryldimethylamine. In Examples 33, 23 and 24, Table 18, Able et al. exemplifies the amination reaction of laural alcohol and dimethylamine, with hydrogen, to give the product, lauryldimethylamine (abstract; Example 1, Table 1; Examples 33, 23 and 24, Table 18; Example 65, Table 33; Table 6, column 17, see “Note” “a 4 ”; column 25, line 38, 45, 50; column 26, line 33) Thus lauryldimethylamine is the tertiary amine product from the amination reaction of dimethylamine with either lauryl alcohol or lauraldehyde. Abe et al. teaches “it is a common practice to introduce a suitable amount of hydrogen gas into the reaction system to distill the formed water and the excess amine (in the case of use of a gaseous amine) together with the hydrogen gas.” (column 7, lines 18-21) Abe et al. teaches “Further, a suitable solvent can be added to the reaction system, followed by distil lation and removal of the formed water in the form of an azeotrope with the solvent.” (column 7, line 25-28) Abe et al. teaches “After completion of the reaction, the reaction mixture itself is subjected to distil lation or filtration to separate the N-substituted amine reaction product from the catalyst. The N-substituted amine obtained by the filtration can be distil led in a very pure form.” (column 8, line 21-26) Abe et al. also exemplifies purification by distillation of the tertiary amine product (column 20, lines 1-3; column 26, lines 32-34; column 28, lines 50-51). Abe et al. further teaches “At the same time, the present inventors have found that the quaternary ammonium salt prepared by the conversion of the N-substituted amine prepared in the presence of this catalyst (c) has a remarkably improved hue compared to that of the conventional quaternary ammonium salt.” (Column 9, lines 17-23) Thus with regard to applicant’s limitation in claim 1, step (2), a distillation step, it would be obvious to distill the reaction liquid that contains the tertiary amine product, along with containing solvent, formed water and a water solvent azeotrope. The azeotrope of water and solvent would be considered “low-boiling point” as compared to the tertiary amine product, since it is removed from the reaction system by distillation. The distillation of the reaction liquid would thus separate the low boiling point azeotrope from the amine product contained in the concentrate, which is a common purification technique that removes solvent water azeotropes from a product mixture. Also with regard to applicant’s limitation in claim 6 for the filtration step to be after the amination step and before the distillation step, because Abe et al. teaches the reaction mixture can be filtered after the reaction is complete and the N-substituted amine filtered product can be further distilled, this would read on applicant’s limitation. Even if it does not, it would be obvious after the amination reaction is complete, to filter the reaction mixture in order to remove insoluble precipitates, and then to distill the amine product to obtain the purified tertiary amine compound. With regard to applicant’s limitation in claim 3 for the concentrate to contain 50% of the tertiary amine product of formula (I). Because Abe et al. exemplifies lauryldimethylamine as the tertiary amine product (in which R = lauryl), in which the lauryl group contains 12 carbons in the hydrocarbon lauryl group, with high yields of 92.3% and 97.6%, it would be reasonable to expect that the lauryldimethylamine product would be present in 50% or more in the concentrate. Even if it does not, it would be obvious to optimize the amount of product in the concentrate in order to increase the yield of the product and minimize impurities in the concentrate of the reaction mixture. Abe et al. teaches “In general, the use of such a branched alcohol, a polyhydric alcohol, or an aldehyde as the starting material brings about an increase in the possibilities of causing side reactions, such as decomposition or condensation of these substances.” (column 29, line 66 – column 30, line 2; column 35, lines 24-29) Furthermore, Abe et al. lists in all their tables in their example section a column titled “Others” that give the percentage of other compound in the product composition. Examples of percentages for these other products are 5.9% and 5.2% (see Examples 23, Table 18 and Example 65, Table 33, respectively). Thus with regard to applicant’s limitation in claim 4 for the concentrate to contain 5% or more of an ester compound, it would be obvious that an ester compound would be a product of a side reaction, and could be formed in 5% of the concentrate, since Abe et al. is well aware of the possibilities of substances resulting from side reactions and because Abe et al. isolates “others” or side products greater than 5% in the reaction product composition. Absent evidence to the contrary, it would be obvious that the concentrate would contain 5% of an ester compound, a side product of the amination reaction resulting from decomposition or condensation. Abe et al. teaches the amination reaction mixture was filtered to recover the catalyst and the amination reaction was repeated using the recovered catalyst. (column 17, lines 55-58; column 24, lines 61-65) Ascertainment of the Difference Between Scope the Prior Art and the Claims (MPEP §2141.012) Abe et al. is deficient in the sense that it does not teach applicant’s centrifugation step. However, Armarego et al. teaches the equivalency of centrifuging and filtering. Armarego et al. teaches the benefits of using centrifugation when solid particles are too fine to be collected from the liquid and when using a filter funnel is too slow to remove the solid from the liquid phase. (page 15, 3 rd full paragraph) Armarego et al. exemplifies a centrifugal force of 12,000 x g. This corresponds to 12,000 G, which would read on applicant’s limitation in claim 2 for a centrifugal force of 1,000 G to 25,000 G. Even if it does not, it would be obvious to optimize the centrifugal force of the centrifugation in order to fractionate the solid particles from the liquid phase. (page 577, last paragraph) Armarego et al. also exemplifies the use of centrifugation in the isolation of a number of compounds that contain a tertiary amine functional group. (page 266, 4 th compound, Crystal Violet Chloride; page 281, 2 nd compound, p-Dimethylaminobenzophenone, page 355, 2 nd compound, Acridine Orange; page 408, second to the last compound, Methylene Blue; page 428, 3 rd to the last compound, Pyronin G) Finding of Prima Facie Obviousness Rationale and Motivation (MPEP §2142-2143) Therefore, it would be prima facie obvious to one of ordinary skill in the art at the time of the invention, to substitute centrifugation for filtration in the work-up of the amination reaction, since Armarego et al. teaches the equivalency of centrifuging and filtering. Furthermore, it would also be obvious to put the centrifugation step after the distillation step, since the order of steps does not impart patentability, and because Armarego et al. teaches the benefits of using centrifugation to separate fine solid particles from the liquid phase. Thus the particular order of the purification steps is obvious in the absence of new or unexpected results. Including a centrifugation step as a last purification step, in order to remove leftover fine solid particles is an obvious optimization tool, especially since Abe et al teaches the need to remove the solid catalyst from the reaction for reuse. Note that an express suggestion to substitute one equivalent component or process for another is not necessary to render such substitution obvious. In re Fout , 675 F.2d 297, 213 USPQ 532 (CCPA 1982). Furthermore, with regard to the limitation for the centrifugal force, the percent of ester compound and the distillation temperature, it is the position of the examiner that one of ordinary skill in the art, at the time of the invention, would through routine and normal experimentation optimize these variables. Because, the art teaches the same reactants, reagents and process steps as the applicant, the examiner asserts that the centrifugal force, the percent of ester compound and the distillation temperature are art recognized result-effective variables. Thus it would be obvious in the optimization process to optimize the centrifugal force, the percent of ester compound and the distillation temperature. The applicant does not show any unusual and/or unexpected results for the limitations stated. Note that the prior art provides the same effect desired by the applicant, the amination reaction of dimethylamine with either an alcohol or aldehdye, and then the isolation and purification of the tertiary amine product . Response to Arguments Applicant’s arguments have been considered but are not persuasive for the following reasons: The examiner acknowledges applicant’s argument that "low-boiling-point compound" is appropriately determined. Applicant also argues that the methyldialkylamine (or dialkylmethylamine) in claim 3 is produced via disproportionation of dimethylamine. The examiner does not agree with applicant’s arguments. With regard to applicant’s assertion for formation of methyldialkylamine (or dialkylmethylamine) by disproportionation, this is confusing because of a few reasons. Disproportionation of dimethylamine would form a primary amine and a tertiary amine product. The tertiary amine product would contain an alkylated dimethylamine, corresponding to dimethylalkylamine, not methyldialkylamine. Further, applicant claims in claim 3 that the two R alkyl or hydrocarbon groups are derived from the aliphatic alcohol or the aliphatic aldehyde and not from the disproportionation of dimethylamine. With regard to applicant’s “low-boiling-point compound”, this term is not limited to applicant’s examples or preferred embodiments. Applicant does not define the metes and bounds of what compound would encompass a “low-boiling-point”, such that one would know what is included and what is excluded. What is considered “low” can differ among chemists. Thus, the metes and bounds of “low” should be clear. The examiner acknowledges applicant’s argument for unexpected superior results for a favorable hue for methyldialkylamine. The examiner does not agree with applicant’s arguments. Applicant has not provided a side by side comparison with the closest prior art presenting data for a superior hue. In lieu of data or evidence in the record, the examiner considers applicant’s argument for unexpected results as opinion and not fact. Furthermore, applicant’s arguments are not commensurate in scope with the claims. Applicant’s claims are not limited to a particular hue or color for methyldialkylamine. Further, Abe et al. has already recognized the benefits of forming compounds with improved hue. Thus one would be motivated to form products with improved hue for the chemical industry. Conclusion No claim is allowed. 07-39 AIA THIS ACTION IS MADE FINAL. 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 mailing 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 Application/Control Number: 18/017,700 Page 2 Art Unit: 1691 Application/Control Number: 18/017,700 Page 3 Art Unit: 1691 Application/Control Number: 18/017,700 Page 4 Art Unit: 1691 Application/Control Number: 18/017,700 Page 5 Art Unit: 1691 Application/Control Number: 18/017,700 Page 6 Art Unit: 1691 Application/Control Number: 18/017,700 Page 7 Art Unit: 1691 Application/Control Number: 18/017,700 Page 8 Art Unit: 1691 Application/Control Number: 18/017,700 Page 9 Art Unit: 1691 Application/Control Number: 18/017,700 Page 10 Art Unit: 1691 Application/Control Number: 18/017,700 Page 11 Art Unit: 1691
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