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 371 of PCT/EP2020/083162 which claims the benefit of EP 19213226.4 with an effective filing date of 03 December 2019 as reflected in the filing receipt mailed on 16 November 2022.
Status of the Claims
Claims 16, 19-27, 30, and 31 are pending.
Claims 16 and 23-25 are currently amended.
Claims 1-15, 17, 18, 28, and 29 are cancelled.
Response to Amendments
Applicant’s arguments and amendments filed 24 February 2026 are acknowledged.
Claim Objections
Applicant’s amendments to claim 16 is sufficient to overcome the
objection of the claim. The claim has been amended to correct the typographical mistake. The objection is withdrawn.
Claim Rejections - 35 USC § 112
Applicant’s amendment to claims 16 and 23 are sufficient to overcome the rejection of claims 16, 19-27, 30, and 31 under 35 U.S.C. 112(b) as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor regards as the invention, the rejection is withdrawn.
Claims 16 and 23 are amended to differentiate between the product amine and the reactant amine. Claim 25 now sufficiently corresponds to the reactant amine. The rejections are withdrawn.
Applicant’s amendment to claims 24 and 25 are sufficient to overcome the rejection claims 24 and 25 under 35 U.S.C. 112(b) as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor regards as the invention.
Claims 24 and 25 are amended to state benzaldehyde. The rejections are withdrawn.
Response to Arguments
Applicant’s arguments filed 24 February 2026 have been fully considered. The statement under 35 U.S.C. § 102(b)(2)(C) is persuasive; however, the rest of the arguments are not persuasive.
Applicant’s 35 U.S.C. § 102(b)(2)(C) Response
Applicant’s statement on pages 5-6 of the remarks filed on 24 February 2026 that “Applicant hereby certifies that the subject matter disclosed in the Ernst reference and the claimed invention were owned or under obligation of assignment to the same person, BASF SE, not later than the effective filing date of the claimed invention”, is sufficient to overcome the rejection of:
Claims 16, 19-27, 30, and 31 under 35 U.S.C. 103 as being unpatentable over Meyer et al. (US6187957, hereinafter Meyer) in view of Ernst et al. (WO2019192903, filed 27 March 2019, hereinafter Ernst).
Due to applicant’s clear and conspicuous statement that the claimed invention of the application under examination and the subject matter disclosed in WO2019192903 to Ernst et al. applied as prior art were owned by the same person or subject to an obligation of assignment to the same person, namely BASF SE, not later than the effective filing date of the claimed invention the rejection is withdrawn, see MPEP 2154.02(c).
Applicant argues that Meyer and Graf do not disclose the limitations as recited in amended claim 16. These arguments have been considered but are not persuasive for the reasons set forth in the reply to arguments below and the maintained grounds of rejection below.
In response to applications arguments on page 6 of the remarks filed on 24 February 2026 “that the combination of these specific reactants with the instant catalyst is not suggested in a manner sufficient to form prima facie obviousness by any of the cited references, alone or in combination”. The test for obviousness is not whether the features of a secondary reference may be bodily incorporated into the structure of the primary reference; nor is it that the claimed invention must be expressly suggested in any one or all of the references. Rather, the test is what the combined teachings of the references would have suggested to those of ordinary skill in the art, see In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981) and MPEP 2145.
“A reference is analogous art to the claimed invention if: (1) the reference is from the same field of endeavor as the claimed invention (even if it addresses a different problem); or (2) the reference is reasonably pertinent to the problem faced by the inventor (even if it is not in the same field of endeavor as the claimed invention).”, see MPEP 2141.01(a).
In this case, as stated on pages 24-25 of the previous office action dated 26 November 2025 (hereinafter POA), Meyer is in the known prior art field of “a process for the amination in the presence of hydrogenation catalysts containing palladium and copper, see Col. 1, Lns. 1-9 and 46-50, and the catalytically active material of the catalyst used in the novel process may furthermore contain one or more elements, or the inorganic or organic compounds thereof, selected from the Group VIII aka VIIIB in which nickel, palladium, and cobalt are metals of this group, see Col. 3, Lns. 44-53”. In addition, as stated on page 24 of the POA, “[o]ne of ordinary skill in the art would have been motivated to choose benzaldehyde because Meyer provides a finite number of identified, predictable solutions, and a person of ordinary skill in the art has good reason to pursue the known options within his or her technical grasp for the benefit of producing an amine having a specific structure corresponding to the starting structures of the reactants, such as PMDETA produced in Example 4 from specific reactants corresponding to the specific product structure, see Col. 11, Ln. 57-Col. 12, Ln. 11; Col. 20, Ln. 34-Col. 22, Ln. 8, and MPEP 2144.05 IIB.”
As stated on page 25 of the POA, Graf is in the known prior art field of “the production of amines by reacting a suitable aldehydes with a suitable polyamine”, where “it is known within the art to react benzaldehyde with ethylene diamine to produce N-benzyl-ethylene-diamine and dibenzyl-ethylene-diamine using a hydrogenation catalyst containing a copper, palladium, and Group VIIIB metal nickel, see Pg. 1, Col. 1, Ln. 1-Col. 2, Ln. 11; Pg. 2, Col. 1, Lns. 51-65”; Claim 1, and is applied to teach the same.
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 Meyer to select benzaldehyde as the reactant aldehyde by applying the differing known aldehydes and any of the diamines as taught by Graf with a reasonable predictability of success for the purpose of, as stated on pages 25-26 of the POA, “producing alkylene-polyamines having a specific diamine structure, such as N-benzyl-ethylene-diamine, etc., corresponding to the starting structures of the specific reactants, such as ethylene diamine with benzaldehyde, by catalytic hydrogenation using known metals that are active in the conversion, such as copper, palladium, and Group VIIIB metals, see Graf, Pg. 1, Col. 1, Ln. 1-Col. 2, Ln. 11; Pg. 2, Col. 1, Lns. 51-65, MPEP 2123 and 2144.05 IIB”, see also 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 Meyer and Graf both teach a process for the amination in the presence of hydrogenation catalysts containing copper, amines, and aldehydes, such as benzaldehyde, 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 copper catalyzed aldehydes and amines of Graf in the copper catalyzed amination process of Meyer.
For the reasons indicated above, applicant’s above arguments are not persuasive.
In response to applications arguments on pages 6-7 of the remarks filed on 24 February 2026 that “[a]s seen in the examples, by way of the specific use of amines, benzaldehyde, and catalyst as required here it is possible to produce the resultant amines in the liquid phase in a surprisingly good yield and selectivity”.
The fact that the inventor has recognized another advantage which would flow naturally from following the suggestion of the prior art cannot be the basis for patentability when the differences would otherwise be obvious, see Ex parte Obiaya, 227 USPQ 58, 60 (Bd. Pat. App. & Inter. 1985). In addition, “[t]o establish unexpected results over a claimed range, applicants should compare a sufficient number of tests both inside and outside the claimed range to show the criticality of the claimed range.” In re Hill, 284 F.2d 955, 128 USPQ 197 (CCPA 1960), see MPEP 716.02(d).
As stated on pages 9-10 of the POA, “Meyer teaches copper and aluminum catalysts including a group VIII metal element, such as palladium, and a carbon, such as graphite, see Col. 2, Ln. 35-Col. 3, Ln. 53, a liquid phase continuous reaction, see Col. 12, Ln. 55-Col. 13, Ln. 55, and benzaldehyde reacted with a diamine, see Col. 7, Lns. 10-67; Col. 11, Ln. 57-Col. 13, Ln. 60. In addition, there is not a sufficient number of tests regarding the gas phase and the effect of differing catalysts. A gas phase reaction was not conducted batchwise. As a result, Applicants have not established unexpected results by comparing a sufficient number of tests inside and outside the claimed range to show the criticality of the claimed liquid phase reaction as compared to the gas phase reaction”.
It is noted, the instant application claims do not recite yield or selectivity. Instant application claim 16 is drawn to specifically “in a liquid phase” reacting benzaldehyde with “an amine selected from the group consisting of ethylene-1,2-diamine (EDA), propylene-1,2-diamine (1,2-PDA), diethylenetriamine (DETA), and triethylenetetramine (TETA)” with a copper catalyst with Cu “in the range from 24% to 98% by weight of oxygen compounds of copper” and Al “in the range from 0.5% to 75% by weight of oxygen compounds of aluminum”. Applicant’s argue, as stated above, this mixture of reactants makes it “possible to produce the resultant amines in the liquid phase in a surprisingly good yield and selectivity”; however, Applicant’s have not provided a proper comparison to the closest prior art and have not established test points inside and outside the claimed range of the mixture of reactants, catalysts composition, reaction in the liquid phase, or reaction in the gas phase in order to support the argument of surprising and unexpected results, see MPEP 716.02(e).
The instant specification is relied upon for any comparison tests/examples, see Pgs. 22-28, Examples. Only two catalysts where prepared and tested, catalyst 1a with 68% by wt. Cu and 13% by wt. Al and catalysts 1b with 64.8% by wt. Cu and 35.2% by wt. Al. There are no comparative tests with catalysts that do not contain Cu or Al. The gas phase reaction of Example 6 is only conducted with catalyst 1b and ethylenediamine. There is no comparative gas phase reaction with catalysts 1a, a catalysts that does not contain Cu or Al, or with the other claimed amines. There are no examples reacting benzaldehyde with propylene-1,2-diamine (1,2-PDA). The instant specification does not provide a proper comparison to the closest prior art and has not established test points inside and outside the claimed range of the mixture of reactants, catalysts composition, reaction in the liquid phase, or reaction in the gas phase in order to support the argument of surprising and unexpected results, see MPEP 716.02(e).
For the reasons indicated above, applicant’s above arguments are not persuasive.
For the reasons indicated above, the rejection of:
Claims 16, 19-27, 30, and 31 under 35 U.S.C. 103 as being unpatentable over Meyer et al. (US6187957, hereinafter Meyer) in view of Graf (US2317757) is maintained.
Maintained Rejections Based on the reply filed on 24 February 2026
In the Spirit of Compact Prosecution
Throughout prosecution the examiner has attempted to identify all objections and clarity issues amongst the claims, applicant is advised that some objections and clarity issues may still remain. For example, claim 24 appears to have a typographical mistake in line 3 of “reaction product per liter of catalysts and hour”.
Going forward, the examiner respectfully requests applicant to perform a detailed review of the claims regarding clarity, grammar, antecedent basis, word spacing, and spelling issues.
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 16, 19-27, 30, and 31 stand rejected under 35 U.S.C. 103 as being unpatentable over Meyer et al. (US6187957, published 13 February 2001, hereinafter Meyer) in view of Graf (US2317757, published 27 April 1943).
Meyer teaches the instant application claims 16, 19-27, and 31 limitations of a process of producing an amine by reacting in the liquid or gaseous phase benzaldehyde with an amine, such as a diamine, see Abstract; Col. 7, Lns. 10-67; Col. 11, Ln. 57-Col. 13, Ln. 55 and Fig. 2, meeting:
The production of an amine, benzaldehyde, and diamine in instant application claim 16;
The amine and benzaldehyde are subjected to hydrogenation by reacting with hydrogen simultaneously and continuously by passing the liquid phase at from 5 to 30 MPa through a fixed-bed reactor packed with a heterogenous copper catalysts at a temperature of 120 to 350° C, the catalyst space velocity is generally from 0.05 to 5 kg of alcohol, aldehyde or ketone per liter of catalyst (bulk volume) per hour, and, the reactor is heated from the outside in a trickle-bed procedure and a liquid-phase procedure, i.e., the reactants are heated in the fixed-bed reactor; therefore, the inlet temperature of reactants is less than the outlet temperature of reactants, see Col. 2, Ln. 35-Col. 3, Ln. 53; Col. 12, Ln. 46-Col. 13, Ln. 60; and Fig. 2, meeting:
The simultaneous liquid phase hydrogenation, copper catalyst, and within the temperature range in instant application claim 16;
The amine preparation in instant application claim 23;
The continuous reaction and within the range of the space velocity in instant application claim 24;
Within the pressure range in instant application claim 26;
The continuous isothermal or adiabatic reaction within the temperature ranges in instant application claim 27;
The amine is used in stoichiometric, substoichiometric or superstoichiometric amounts, based on the alcoholic hydroxyl group or aldehyde group or keto group to be aminated, where in the case of amination of alcohols, aldehydes or ketones with primary or secondary amines, the amine is preferably used in roughly stoichiometric amount per mole of alcoholic hydroxyl group, aldehyde group or keto group to be aminated and the amines are also used in large excess, i.e., a benzaldehyde : diamine ratio of 1:1, 1:2, 1:3, or greater, see Col. 12, Lns. 46-59, meeting within the range in instant application claim 25;
The catalysts prior to reduction with hydrogen has 60% by weight CuO which via calculation by the examiner is 47.94% by weight Cu, the catalyst prior to reduction has 48% by weight CuO which via calculation by the examiner is 38.35% by weight Cu, the catalyst prior to reduction has 41.5% by weight Al2O3 as half of the TiO2 amount of 83% by weight which via calculation by the examiner is 21.96% by weight Al, and, the catalyst comprises 83% by weight TiO2 which via calculation by the examiner is 49.75% by weight Ti and the catalyst comprises 32% by weight TiO2 which via calculation by the examiner is 19.18% by weight Ti, see Col. 2, Ln. 35-Col. 3, Ln. 53; Col. 15, Lns. 36-52, Catalyst G, Claims 1 and 4, meeting:
Within the Cu, Al, and Ti, ranges in instant application claim 16 and in instant application claim 19;
The catalyst comprises 2 to 40% metallic copper, specifically 16% metallic copper, and the catalyst is prepared by a process where copper nitrate, aluminum oxide, and titanium oxide are mixed, then graphite and metallic copper powder are added and mixed, then the material is shaped to give the copper oxide catalyst material, see Col. 2, Ln. 35-Col. 3, Ln. 43, Col. 15, Lns. 36-52, Catalyst G, Claims 1-4, and 6, meeting:
Within the elemental copper range in instant application claim 20;
The process of preparing the catalyst in instant application claim 21;
The additional graphite in instant application claim 22; and,
The catalyst having 60% by weight CuO + 40% by weight TiO2, where half of the TiO2 is replaced by Al2O3 leads to 60% by weight CuO + 20% by weight Al2O3 + 20% by weight TiO2 leads to a catalyst with 80 weight % CuO plus Al2O3 based on the total amount of metal oxides in the catalyst, see Col. 2, Ln. 35-Col. 3, Ln. 43, meeting within the range of CuO and AlO compounds in instant application claim 31.
In regard to the instant application claim 21 limitations of “the copper oxide catalyst, prior to reduction thereof with hydrogen, is preparable by a process …”, see MPEP 2113(I) stating “even though product-by-process claims are limited by and defined by the process, determination of patentability is based on the product itself. The patentability of a product does not depend on its method of production. If the product in the product-by-process claim is the same as or obvious from a product of the prior art, the claim is unpatentable even though the prior product was made by a different process.” In re Thorpe, 777 F.2d 695, 698, 227 USPQ 964, 966 (Fed. Cir. 1985) (citations omitted)”. Meyer teaches the copper oxide catalyst; therefore, the process of production is not given patentable weight; however, Meyer also teaches the process of production.
Meyer teaches benzaldehyde in a list of possible aldehyde choices. It would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to have chosen an aldehyde of specific structure, such as benzaldehyde, in order to produce an amine having a specific structure corresponding to the benzaldehyde with a reasonable expectation of success. One of ordinary skill in the art would have been motivated to choose benzaldehyde because Meyer provides a finite number of identified, predictable solutions, and a person of ordinary skill in the art has good reason to pursue the known options within his or her technical grasp for the benefit of producing an amine having a specific structure corresponding to the starting structures of the reactants, such as PMDETA produced in Example 4 from specific reactants corresponding to the specific product structure, see Col. 11, Ln. 57-Col. 12, Ln. 11; Col. 20, Ln. 34-Col. 22, Ln. 8, and MPEP 2144.05 IIB.
Meyer does not teach:
The instant application claim 16 limitations of an amine selected from the group consisting of ethylene-1,2- diamine (EDA), propylene-1,2-diamine (1,2-PDA), diethylenetriamine (DETA), and triethylenetetramine (TETA); and,
The limitations of instant application claim 30.
Meyer teaches a process for the amination in the presence of hydrogenation catalysts containing palladium and copper, see Col. 1, Lns. 1-9 and 46-50, and the catalytically active material of the catalyst used in the novel process may furthermore contain one or more elements, or the inorganic or organic compounds thereof, selected from the Group VIII aka VIIIB in which nickel, palladium, and cobalt are metals of this group, see Col. 3, Lns. 44-53.
Graf relating to the production of amines by reacting a suitable aldehydes with a suitable polyamine teaches it is known within the art to react benzaldehyde with ethylene diamine to produce N-benzyl-ethylene-diamine and dibenzyl-ethylene-diamine using a hydrogenation catalyst containing a copper, palladium, and Group VIIIB metal nickel, see Pg. 1, Col. 1, Ln. 1-Col. 2, Ln. 11; Pg. 2, Col. 1, Lns. 51-65, meeting:
The specific diamines in instant application claim 16; and,
The specific preparation in instant application claim 30.
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 the aldehyde and diamine of Meyer to select benzaldehyde as the aldehyde and 1,2-ethanediamine (1,2-EDA) as the diamine as taught by Graf with a reasonable predictability of success for the purpose of producing alkylene-polyamines having a specific diamine structure, such as N-benzyl-ethylene-diamine, etc., corresponding to the starting structures of the specific reactants, such as ethylene diamine with benzaldehyde, by catalytic hydrogenation using known metals that are active in the conversion, such as copper, palladium, and Group VIIIB metals, see Graf, Pg. 1, Col. 1, Ln. 1-Col. 2, Ln. 11; Pg. 2, Col. 1, Lns. 51-65, MPEP 2123 and 2144.05 IIB.
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 art, relevant for all they contain, see MPEP 2123, and both Meyer and Graf teach reacting a diamine with benzaldehyde to produce an amine by hydrogenation using a copper, palladium, and Group VIII/VIIIB metal catalyst, a person of ordinary skill in the art has good reason to produce the desired amine of specific diamine structure by pursuing the known options within their technical grasp, such as selecting benzaldehyde and EDA reactants, before the effective filing date of the claimed invention for the benefit of producing alkylene-polyamines having a specific diamine structure, such as N-benzyl-ethylene-diamine, etc., corresponding to the starting structures of the specific reactants, such as ethylene diamine with benzaldehyde, by catalytic hydrogenation using known metals that are active in the conversion, such as copper, palladium, and Group VIIIB metals, see Graf, Pg. 1, Col. 1, Ln. 1-Col. 2, Ln. 11; Pg. 2, Col. 1, Lns. 51-65, MPEP 2123 and 2144.05 IIB.
MPEP 2123, 2141, and 2144.05 IIB.
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.
In addition, “[t]he 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 concentration of reactants and the catalysts active materials, “is the optimum combination of percentages.” In re Hoeschele, 406 F.2d 1403, 160 USPQ 809 (CCPA 1969), see MPEP 2144.05.
Selection of a known material, such as diamines and copper hydrogenation 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.
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 temperatures, pressures, and reactant concentrations, “or degree, or the substitution of equivalents doing the same thing as the original invention, by substantially the same means,” such as catalysts containing palladium and copper, “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.
Conclusion
No claims are allowed.
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 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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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Scarlett Yen-Ye 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.
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/YO/Examiner, Art Unit 1692
/FEREYDOUN G SAJJADI/Supervisory Patent Examiner, Art Unit 1699
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