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 .
Priority
This application is a Continuation of PCT/JP2020/028915 which claims the benefit of JP 2019-152113 with an effective filing date of 22 August 2019 as reflected in the filing receipt mailed on 28 January 2022.
Status of the Claims
Claims 5, 12-14, 17, and 18 are pending.
Claim 18 is new.
Claim 17 is current amended.
Claims 4 and 6-11 are currently cancelled.
Claims 1-3, 15, and 16 were previously cancelled.
Response to Amendments
Applicant’s amendments filed 04 February 2026 are acknowledged.
Claim Rejections - 35 USC § 103
Applicant’s amendment to claim 17 reducing the cyclic structure alkyl group to 1 carbon atom which is taught by Yasukouchi ‘584 and cancellation of claims are sufficient to overcome the rejections of claims 4-14 and 17 under 35 U.S.C. 103 as being unpatentable over Yasukouchi et al. (WO 2019049584, cited by applicants 01 April 2022, hereinafter Yasukouchi ‘584) in view of Aavula et al. (US20170210745, hereinafter Aavula). Due to the amendment to claim 17 and cancellation of claims, the rejection is withdrawn and a new ground(s) of rejection is/are provided below.
Response to Arguments
Applicant’s arguments filed 04 February 2026 have been fully considered but they are not persuasive.
Applicant argues that Yasukouchi ‘584 and Aavula do not disclose the limitations as recited in amended claim 17. These arguments have been considered but are either moot or not persuasive for the reasons set forth in the response to arguments and the new grounds of rejection below.
Applicant’s arguments throughout the remarks filed on 04 February 2026 with respect to Aavula have been considered but are moot because the new ground of rejection does not rely on Aavula applied in the prior rejection of record for any teaching or matter specifically challenged in the argument.
In response to applicant’s argument on page 6 of the remarks filed on 04 February 2026 that “it is clear that Yasukouchi” recommends “diisopropylethylamine”. “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”, see 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)) and MPEP 2123; “[d]isclosed examples and preferred embodiments do not constitute a teaching away from a broader disclosure or nonpreferred embodiments”, see In re Susi, 440 F.2d 442, 169 USPQ 423 (CCPA 1971) and MPEP 2123; and, “[t]he prior art’s mere disclosure of more than one alternative does not constitute a teaching away from any of these alternatives because such disclosure does not criticize, discredit, or otherwise discourage the solution claimed”, see In re Fulton, 391 F.3d 1195, 1201, 73 USPQ2d 1141, 1146 (Fed. Cir. 2004) and MPEP 2123.
In this case, Yasukouchi ‘584 teaches the use of a variety of tertiary amine nitrogen containing compounds, both cyclic and non cyclic, as long as the “nitrogen-containing organic compound [has] no reactive group with phosgene”, see Paras. [0039]-[0041]. Therefore, Yasukouchi ‘584 does not “criticize, discredit, or otherwise discourage” the use of any nitrogen containing compound as long as the nitrogen containing compound has no reactive group with phosgene, see MPEP 2145 X.D.1.
For the reasons indicated above, applicant’s above argument is not persuasive.
In response to applicant’s arguments on pages 6-7 of the remarks filed on 04 February 2026 that Yasukouchi contains “teachings that lead to an increase in by-products, rather than contributing to solve the problem” of decreasing the by-products “but rather contain teachings in the opposite direction (teaching away)”.
Yasukouchi ‘584 does teach the inventive method is drawn to reducing impurities or by-products, see Paras. [0009];[0027];[0034], where when the phosgene and tertiary amine are not permitted to react together a product with by-products or impurities having “0 area % vs product area” is produced, see Paras. [0034];[0119]-[0124], Examples 4-6; Fig. 1; while, if the phosgene and tertiary amine are permitted to react together a product with by-products or impurities having “72 area % vs product area” is produced, see Paras. [0130]-[0131], Comparative Example 1; Fig. 3.
As stated above, Yasukouchi ‘584 does not “criticize, discredit, or otherwise discourage” the use of any nitrogen containing compound as long as the nitrogen containing compound has no reactive group with phosgene, see MPEP 2145 X.D.1; therefore, Yasukouchi ‘584 does not teach away from the use of a variety of nitrogen containing compounds.
For the reasons indicated above, applicant’s above arguments are not persuasive.
New and Maintained Rejections Based on Amendments to the Claims in the reply filed on 04 February 2026
For clarity between the below new and maintained rejections, the specific new rejections are in italics.
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.
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 12-14 and 17 are newly rejected and claim 18 is rejected under 35 U.S.C. 103 as being unpatentable over Yasukouchi et al. (WO2019049584A1, published 14 March 2019, hereinafter Yasukouchi ‘584). WO2019/049584A1 is translated as US2020/0207717A1 which is serving as the English language equivalent and all citations in this action pertain to this US application.
Yasukouchi ‘584 teaches the claims 12-14 and 17 limitations of a method of producing a carbonyl compound, see Paras. [0010]-[0027] and Figs. 1-2. In a flow type reactor raw material liquid A containing a triphosgene in organic solvent solution is introduced separately in feed line 11, raw material liquid B, having no solvent or in an organic solvent, containing a combination of tertiary amines, such as 1,8-diazabicyclo[5,4,0]undec-7-ene
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, N-methylmorpholine
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, pyridine
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, a trialkylamine, and a diisoalkylamine, such as a diisopropylbutylamine
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and diisopropylethylamine
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, are introduced separately in feed line 12, and raw material liquid C, having no solvent or in an organic solvent and at least one functional group capable of reacting with phosgene, containing a −OC(═O)NH2 group aka a primary amine is introduced separately in feed line 14, see Paras. [0033]-[0034];[0036];[0039];[0045];[0080] and Fig. 1, where throughout the process side reactions are prevented because water does not exist or is 1 wt% or less, i.e., a lower limit of 0% or 0 ppm water, see Para. [0099], meeting:
The carbonyl compound, introducing step including the specific solutions in separate flow channels, within the range of the water content of the non aqueous organic solvents, the cyclic tertiary amine, and the morpholine ring in instant application claim 17;
The specific morpholine ring structure bonded to an alkyl group having 1 carbon atom, N-methylmorpholine
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, in instant application claim 17;
The primary amine in instant application claim 13 and in instant application claim 14;
The triphosgene solution 11 and the combination of tertiary amines solution 12 is joined and mixed at 15 to prepare phosgene in the first flow reactor 21, see Paras. [0033]-[0034];[0050] and Fig. 1, the prepared phosgene solution 13 is then mixed with the primary amine solution 14 at mixer 16 in order to react the phosgene with the primary amine in second flow reactor 18 where the carbonyl product is obtained in tank 32, see Paras. [0019];[0033];[0049]-[0051];[0092], meeting:
The sequentially joining step and obtaining step in instant application claim 17; and,
The limitations in instant application claim 12.
Regarding the limitations of instant application claim 17, Yasukouchi ‘584 teaches “when a solution containing a reaction substrate and an amine and a solution containing triphosgene are reacted in a single reaction field in a conventional flow reactor, the reaction yield may not be improved sufficiently. The reason therefore is assumed to be as follows: 1) before phosgene is formed from triphosgene, an impurity (hereinafter may be referred to as a by-product) is produced due to a side reaction of triphosgene or diphosgene with the reaction substrate, and 2) since the produced impurity is relatively stable, it does not undergo decomposition (phosgenation) and remains even in the presence of amines. By adopting the method of one or more embodiments of the present invention, since the reaction substrate is reacted after sufficiently forming phosgene from triphosgene, the production of impurity due to the above side reaction can be sufficiently suppressed, and hence the yield of the desired organic compound is improved.”, see Para. [0034]. To clarify, first the tertiary amine nitrogen containing compound B reacts with triphosgene A to result in the creation of phosgene as the product of the reaction loop first flow reactor 21, where by the time a “solution containing phosgene (first reaction solution) is obtained as a product of the first reaction” the tertiary amine is spent resulting in little to no side reactions between the phosgene and the tertiary amine, “then the reaction substrate” C “having a reactive group with phosgene and the phosgene above generated are reacted in another reaction field in the second flow reactor 22, whereby the yield of a desired organic compound is remarkably improved”, see Fig. 1; Paras. [0017];[0032]-[0034]. Yasukouchi ‘584 teaches the above method leads to a product with by-products or impurities having “0 area % vs product area”, see Paras. [0119]-[0124], Examples 4-6; Fig. 1; while, if the phosgene and tertiary amine are permitted to react together a product with by-products or impurities having “72 area % vs product area” is produced, see Paras. [0130]-[0131], Comparative Example 1; Fig. 3.
With regard to the instant application claim 17 functional limitation of “wherein a content of a by-product via a quaternary salt, which is generated by a reaction between the tertiary amine and the phosgene, is less than 8% by mass”. Yasukouchi ‘584 teaches the tertiary amine and phosgene are not permitted to react resulting in a product with by-products or impurities having “0 area % vs product area”, see Paras. [0034];[0119]-[0124], Examples 4-6; Fig. 1; therefore, a prima facie case of either anticipation or obviousness has been established, see In re Best, 562 F.2d 1252, 1255, 195 USPQ 430, 433 (CCPA 1977) and MPEP 2112. Since “[p]roducts of identical chemical composition can not have mutually exclusive properties” and “[a] chemical composition and its properties are inseparable”, see In re Spada, 911 F.2d 705, 709, 15 USPQ2d 1655, 1658 (Fed. Cir. 1990) and MPEP 2112, Yasukouchi ‘584 inherently teaches less than 8% by mass of a by-product of a quaternary salt generated by the reaction between the tertiary amine and the phosgene is produced, meeting and within the range of by-product produced in instant application claim 17.
In addition, ““the discovery of a previously unappreciated property of a prior art composition, or of a scientific explanation for the prior art’s functioning, does not render the old composition patentably new to the discoverer.” Atlas Powder Co. v. IRECO Inc., 190 F.3d 1342, 1347, 51 USPQ2d 1943, 1947 (Fed. Cir. 1999). Thus the claiming of a new use, new function or unknown property which is inherently present in the prior art does not necessarily make the claim patentable. In re Best, 562 F.2d 1252, 1254, 195 USPQ 430, 433 (CCPA 1977)”, see MPEP 2112 I.
Regarding the limitations of instant application claim 18, Yasukouchi ‘584 teaches the nitrogen containing compound is a tertiary amine, see Para. [0039], where the molar ratio of (tertiary amine/triphosgene) is 3/1 to 8/1 in joining part/first mixing unit 15, see Paras. [0032]-[0034];[0042]; Fig. 1, meeting within the ratio range at the joining part in instant application claim 18.
Yasukouchi ‘584 does not teach the limitations of the above instant application claims in one single express embodiment or Example.
In reference to the above claims, it would have been obvious to one of ordinary
skill in the art, before the effective filing date of the claimed invention, to have modified Yasukouchi ‘584 to choose the optimal tertiary amine nitrogen containing compound, primary amine, mixing order to limit the production of by-products/impurities, and reactant molar ratios with a reasonable predictability of success for the purpose of efficiently producing the desired carbonyl compound at high yield with minimal by-products and hazardous reactants, see Paras. [0003];[0008]-[0009];[0018]-[0019];[0034].
A rationale to support a conclusion that the claim would have been obvious is that a particular known technique was recognized as part of the ordinary capabilities of one skilled in the art. Another rationale to support a conclusion that the claim would have been obvious is that the substitution of one known element for another yields predictable results to one of ordinary skill in the art. One of ordinary skill in the art would have been capable of modifying Yasukouchi ‘584 to select the optimal phosgenation reaction conditions by applying the differing known reactants and conditions as taught by Yasukouchi ‘584 with a reasonable predictability of success for the purpose of efficiently producing the desired carbonyl compound at high yield with minimal by-products and hazardous reactants, see Paras. [0003];[0008]-[0009];[0018]-[0019];[0034]; and MPEP 2143 I. B-D.
Furthermore, an “obvious to try” rationale may support a conclusion that a claim would have been obvious where one skilled in the art is choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success, see MPEP 2145 X.B. Since Yasukouchi ‘584 teaches tertiary amine nitrogen containing compounds, primary amines, a mixing order to limit the production of by-products/impurities, and reactant molar ratios, the prior art contains “detailed enabling methodology, a suggestion to modify the prior art to produce the claimed invention, and evidence suggesting the modification would be successful”, see MPEP 2145 X.B.; therefore, it would have been obvious for one of ordinary skill in the art at the time the invention was made to try the differing phosgenation reaction conditions as taught by Yasukouchi ‘584 in order to produce the desired carbonyl compound.
As stated in Sakraida v. Ag Pro, Inc., 425 U.S. 273, 189 USPQ 449, reh’g denied,
426 U.S. 955 (1976), “[w]hen a work is available in one field of endeavor, design
incentives and other market forces can prompt variations of it, either in the same field
or a different one. If a person of ordinary skill can implement a predictable variation, §103 likely bars its patentability. For the same reason, if a technique has been used to
improve one device, and a person of ordinary skill in the art would recognize that it
would improve similar devices in the same way, using the technique is obvious unless its actual application is beyond his or her skill”, see MPEP 2141.
Selection of known materials, such as tertiary amine nitrogen containing compounds and primary amines, based on their suitability for its intended use supported a prima facie obviousness determination in Sinclair & Carroll Co. v. Interchemical Corp., 325 U.S. 327, 65 USPQ 297 (1945), see MPEP 2144.07.
“The normal desire of scientists or artisans to improve upon what is
already generally known provides the motivation to determine where in a disclosed set
of percentage ranges”, such as the mass % impurities/by-products, “is the optimum combination of percentages.” In re Hoeschele, 406 F.2d 1403, 160 USPQ 809 (CCPA 1969), see MPEP 2144.05.
In addition, “[i]t is a settled principle of law that a mere carrying forward of an original patented conception involving only change of form, proportions,” such as the molar ratio of reactants, “or degree, or the substitution of equivalents doing the same thing as the original invention, by substantially the same means, is not such an invention as will sustain a patent, even though the changes of the kind may produce better results than prior inventions. In re Williams, 36 F.2d 436, 438, 4 USPQ 237 (CCPA 1929)”, see MPEP 2144.05.
Claim 5 is newly rejected under 35 U.S.C. 103 as being unpatentable over Yasukouchi et al. (WO2019049584A1, published 14 March 2019, hereinafter Yasukouchi ‘584), as applied to claims 12-14, 17, and 18 in the 35 USC 103 rejection above, in view of Fukuchi et al. (WO2018070532A1, published 19 April 2018, hereinafter Fukuchi). WO2019/049584A1 is translated as US2020/0207717A1 which is serving as the English language equivalent and all citations in this action pertain to this US application. WO2018070532A1 is translated as EP3527595A1 which is serving as the English language equivalent and all citations in this action pertain to this EP application.
Yasukouchi ‘584 does not teach the limitations of instant application claim 5.
Yasukouchi ‘584 is in the known prior art of phosgenation reactions to produce “a compound having a isocyanate” structure, see Paras. [0009]-[0019], where a tertiary amine, such as a morpholine, is used as a catalyst, see Paras. [0039];[0042]-[0045].
Fukuchi is in the known prior art field of producing isocyanate compounds by phosgenation reactions of tertiary amines, see Paras. [0048]-[0050];[0264]-[0266], and the use of tertiary amines as catalysts, see Paras. [0103];[0111].
Regarding the limitations of instant application claim 5, Fukuchi teaches phosgenation reactions to produce a compound having a isocyanate structure, see Paras. [0048]-[0050];[0264]-[0266], where the tertiary amines “N-methylmorpholine, N-ethylmorpholine, N-propylmorpholine, N-butylmorpholine, N-sec-butylmorpholine, N-tert-butylmorpholine, N-isobutylmorpholine, and quinuclidine; and mixtures of any of these amines” may be used as catalysts, see Paras. [0068];[0103],
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, meeting the morpholine branched C4 alkyl group tertiary amine in instant application claim 5.
It would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to have modified the morpholine tertiary amine catalyst of Yasukouchi ‘584 to use the alkyl branched morpholine tertiary amine catalysts as taught by Fukuchi with a reasonable predictability of success for the purpose of efficiently producing an isocyanate compound of the desired structure with the desired properties, such as “weather resistance, chemical resistance, abrasion resistance, or the like”, see Paras. [0003];[0048]-[0050];[0068];[0103];[0111].
The rationale to support a conclusion that the claim would have been obvious is that a particular known technique was recognized as part of the ordinary capabilities of one skilled in the art. One of ordinary skill in the art would have been capable of modifying the morpholine tertiary amine catalyst of Yasukouchi ‘584 by applying the known alkyl branched morpholine tertiary amine catalysts as taught by Fukuchi with a reasonable predictability of success for the purpose of efficiently producing an isocyanate compound of the desired structure with the desired properties, such as “weather resistance, chemical resistance, abrasion resistance, or the like”, see Paras. [0003];[0048]-[0050];[0068];[0103];[0111]; and MPEP 2143 I. B-D.
The rationale to support a conclusion that the claim would have been obvious is that “a person of ordinary skill has good reason to pursue the known options within his or her technical grasp. If this leads to the anticipated success, it is likely that product [was] not of innovation but of ordinary skill and common sense”, see MPEP 2143 I.E. Since patents are part of the literature of the prior art relevant for all they contain, see MPEP 2123, and Yasukouchi ‘584 and Fukuchi both teach the use morpholine tertiary amine catalysts, a person of ordinary skill in the art has good reason to modify Yasukouchi ‘584 by relying upon Fukuchi before the effective filing date of the claimed invention for knowledge generally available within the cyclic tertiary amine catalyst within the phosgenation reaction art, see MPEP 2143 B & G and 2141, for the benefit of efficiently producing an isocyanate compound of the desired structure with the desired properties, such as “weather resistance, chemical resistance, abrasion resistance, or the like”, see Paras. [0003];[0048]-[0050];[0068];[0103];[0111]; and, MPEP 2141 and 2143 I. B-D.
Furthermore, an “obvious to try” rationale may support a conclusion that a claim would have been obvious where one skilled in the art is choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success, see MPEP 2145 X.B. Since both Yasukouchi ‘584 and Fukuchi teach the use morpholine tertiary amine catalysts, the prior art contains “detailed enabling methodology, a suggestion to modify the prior art to produce the claimed invention, and evidence suggesting the modification would be successful”, see MPEP 2145 X.B.; therefore, it would have been obvious for one of ordinary skill in the art at the time the invention was made to try the alkyl branched morpholine tertiary amine catalysts as taught by Fukuchi as the morpholine tertiary amine catalyst of Yasukouchi ‘584.
As stated in Sakraida v. Ag Pro, Inc., 425 U.S. 273, 189 USPQ 449, reh’g denied,
426 U.S. 955 (1976), “[w]hen a work is available in one field of endeavor, design
incentives and other market forces can prompt variations of it, either in the same field
or a different one. If a person of ordinary skill can implement a predictable variation, §103 likely bars its patentability. For the same reason, if a technique has been used to
improve one device, and a person of ordinary skill in the art would recognize that it
would improve similar devices in the same way, using the technique is obvious unless its actual application is beyond his or her skill”, see MPEP 2141.
Selection of a known material, such as morpholine tertiary amine catalysts, based on its suitability for its intended use supported a prima facie obviousness determination in Sinclair & Carroll Co. v. Interchemical Corp., 325 U.S. 327, 65 USPQ 297 (1945), see MPEP 2144.07.
Conclusion
No claims are allowed.
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 Y. Lynnette Kelly-O'Neill whose telephone number is (571)270-3456. The examiner can normally be reached Tuesday-Friday, 8:30 a.m. - 6:30 p.m., EST, with Flex Time.
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/YO/Examiner, Art Unit 1692
/FEREYDOUN G SAJJADI/Supervisory Patent Examiner, Art Unit 1699
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