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 .
Applicant’s amendment dated 14 July 2025 is hereby acknowledged. Claims 1, 6, 7, 17, and 24-28 as amended are pending. All outstanding objections and rejections made in the previous Office Action, and not repeated below, are hereby withdrawn.
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior office action.
New grounds of rejection set forth below are necessitated by applicant’s amendment filed on 14 July 2025. In particular, claims 25-28 are new. For this reason, the present action is properly made final.
Claim Rejections - 35 USC § 112
Claims 1, 6, 7, 17, and 24-28 are rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, as failing to comply with the written description requirement. The claim(s) contains subject matter which was not described in the specification in such a way as to reasonably convey to one skilled in the relevant art that the inventor or a joint inventor, or for applications subject to pre-AIA 35 U.S.C. 112, the inventor(s), at the time the application was filed, had possession of the claimed invention.
Claim 1 as been amended from the original claims to recite a ratio between 1,2-ethylenediamine and carbonyl groups in a range of 3/1 to 4/1. The specification discuss such a ratio, and describes ranges of 2/1 and greater, 3/1 and greater, and 4/1 and greater. None of these ranges in the specification set forth an upper bound. All of the examples of applicant’s specification use the reactants in a 5/1 ratio.
Applicant’s specification teaches that the amount of monosubstituted amine compound is enhanced with higher ratios of the amine compound to the carbonyl compound. Nowhere is it suggested that this improvement decreases at ratios higher than 4/1. Neither does the specification provide any examples of amines prepared with a ratio in the recited range. Applicant has amended to require an upper bound of 4/1, and has provided experimental evidence demonstrating that the process in this range provides higher yield of monosubstituted ethylenediamine than other amounts, including higher ratios such as 5/1. This finding appears to be directed to a new invention not contemplated in the specification and claims as filed. As such, it does not appear that applicant had possession of the recited invention, specifically the upper bound of 4/1.
The Office recommends amending to a range of 3/1 or greater to overcome this rejection.
Claim Rejections - 35 USC § 103
Claim(s) 1, 6, 7, 17, and 24-28 are rejected under 35 U.S.C. 103 as being unpatentable over US 2,317,757 (“Graf”) in view of Mokrov et al., “Synthesis and selected properties of N-substituted pyrrolo[2,1-c]-1,3-diazacycloalkano[1,2-α]pyrazinones”, Russ. Chem. Bull. Int’l Ed. 59(6), 1254-1266 (2010) (“Mokrov”) and WO 2013/068502 A2 (“Burckhardt”).
The citations to WO 2013/068502 A2 refer to US 2014/0288247, the US national stage version.
As to claims 1, 24, and 27, Graf teaches methods for producing alkylene polyamines condensed with aldehydes and ketones.
Graf specifically teaches, in example 7, p. 2, production of N-benzylethylenediamine, which is an amine of formula (I) where n is 0 and R is H as required by claims 1-3. Graf teaches reductively alkylating benzaldehyde, which is an aldehyde of formula (II) where n is 0, with ethylenediamine under hydrogenation (molecular hydrogen) at a pressure of 70 atmospheres (71 bar), which is within the recited range of claims 1 and 27. Example 7 of Graf refers to Example 1, p. 1 for working up, which includes removal of unreacted ethylenediamine by distillation, and distilling out N-benzylethylenediamine, a reaction product required by claim 8.
While Graf teaches an excess of ethylenediamine molecules over aldehyde groups calculated as 1.67:1, it does not exemplify a ratio of at least 3:1 or 3:1-4:1 as required by claim 23. However, col. 1, lines 1-10 of Graf teach the utility of using aldehyde in smaller quantity (thus excess diamine) so as to favor monosubstitution products while obtaining unreacted amine. Moreover, other examples of Graf teach at least a 2:1 ratio (see example 8, p. 2, teaching 2:1 ratio; example 4, p. 2, calculated as a 7:1 ratio of laurinaldehyde to ethylenediamine), which include the recited ranges, and as such, the use of ratios of 2:1 and excess of 3:1-4:1 is an obvious modification suggested by Graf. In addition, Mokrov teaches reductive alkylation with molecular hydrogen of N-benzylethylenediamine (Mokrov, p. 1255, Scheme 2, compound 7a). While Mokrov does not teach the same pressures as recited, Mokrov teaches the utility of a threefold excess of diamines in the reaction in order to reduce formation of byproducts (p. 1254-1255).
Both Graf and Mokrov teach mixing, thus reacting the amine and aldehyde prior to hydrogenation, but do not discuss a continuous hydrogenation process in a continuous hydrogenation apparatus as required by claims 1 and 24. Burckhardt teaches reductive alkylation of aldehydes with amines, and teaches a general procedure of mixing the aldehyde and amine, followed by pressure hydrogenation in a continuous apparatus with a hydrogenation catalyst therein (para. 0164). The method of Burckhardt provides a continuous method of carrying out hydrogenation, and is therefore an obvious modification over Graf to provide continuous operation.
As to claim 6, Graf teaches separation of amines by boiling (distillation, see ref. to workup of examples 1 and 2), which would be expected to remove the recited amount.
As to claim 7, Graf teaches separation by boiling point (distillation) to obtain the purified product (example 8).
As to claim 17, Graf teaches adding the ethylenediamine and benzophenone, thus reacting, prior to addition of catalyst and hydrogenation (example 7). The ethylenediamine is removed only after hydrogenation.
As to claims 26 and 28, Graf teaches reacting at temperatures of 80 to 100 degrees C (example 7), which is in the range required by claims 26 and 28.
As to claim 25, Graf does not teach the recited catalysts; however, Graf teaches that ordinary catalysts used in hydrogenation may be used (p. 1, 1st col., 47-51). Mokrov, Scheme 2, p. 1255, shows the use of Pd/C catalyst for the benzylation of ethylenediamine at a 3:1 amine:benzaldehyde ratio. Moreover, Burckhardt teaches the utility of Pd/C catalyst, as well as the other recited catalysts for reaction of aldehydes with amines in a continuous process (para. 0056). As such, the use of the recited catalysts is an obvious modification as taught to be suitable for reductive alkylation of the system by Mokrov, and as suitable for the continuous reductive alkylation under hydrogen by Burckhardt.
Response to Arguments
Applicant's arguments filed 14 July 2025 have been fully considered but they are not persuasive.
Applicant’s arguments against the rejection under 35 USC 112(a) are not persuasive. These claims are distinguished by that applicant is providing evidence for unexpected results associated with an upper bound on the ratio of amine to benzaldehyde that was not stated in the application as filed. Applicant argues that the evidence provided in declarations suggests unexpected results in the range of 3:1 to 4:1; however, since this upper bound was not stated in the specification, and the specification shows no examples in this preferred range, the only examples in this preferred range are in a declaration provided after filing. These facts suggest that the new limitation of 3:1 to 4:1 is directed to a new invention not contemplated in the specification and claims as filed.
Applicant’s arguments regarding the combination of Graf and Mokrov are not persuasive. Mokrov, while carrying out a reaction at atmospheric pressure, does not suggest any superiority of the use of atmospheric pressure, while it does teach the utility of a 3/1 ratio for reducing byproducts. Graf teaches the utility of using higher pressure of molecular hydrogen to favor the monoamine compounds, and also suggests that higher proportions of the monoamine can be obtained using excess amine.
Applicant argues that unexpected effect of lower amount of byproducts occurs in the recited range. However, Mokrov already teaches the utility of a ratio in the recited range to reduce byproducts. Therefore, the recited range is already an obvious modification for reducing byproducts. As such, the evidence provided by applicant simply recognizes a modification known in the art, and is not an unexpected effect. Applicant further has not demonstrated any unexpected effects from continuous hydrdogenation.
Conclusion
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 KREGG T BROOKS whose telephone number is (313)446-4888. The examiner can normally be reached Monday to Friday 9 am to 5:30 pm.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Arrie Reuther can be reached at (571)270-7026. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/KREGG T BROOKS/Primary Examiner, Art Unit 1764