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 2/20/26. Claims 1-20 are pending in this application. Claims 8-11 and 13-15 remain withdrawn.
As a result, claims 1-7, 12-16 and 17-20 are being examined in this Office Action.
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 1-7, 12-16 and 17-20 remain rejected under 35 U.S.C. 103(a) as being unpatentable over Yamamoto et al. (US 20160207877, pub date July 21, 2016, in applicant’s IDS filed on 1/6/23), in view of Okawa et al. (US 5969187, pub date Oct. 19, 1999).
Determination of the Scope and Content of the Prior Art
(MPEP §2141.01)
Yamamoto et al. teaches an isomerization method for bis(aminomethyl)cyclohexane (BAC) by an isomerization step using an imine compound, and either an alkali metal, an alkali metal-containing compound, an alkaline earth metal or an alkaline earth metal containing compound, to control the isomer ratio, which can increase the trans-trans amount. The reaction to produce the imine compound used in the isomerization is obtained by a dehydration and condensation reaction of an amine and an aldehyde. The preferred amine is BAC, since this increases the purity of the BAC product. The amount of aldehyde relative to the BAC amine is preferably 0.20 to 5.0 mol %. This range suppresses side reactions and improves yields. The amount of the metal compounds relative to the BAC amine is preferably 0.5 to 2 mole %. This range allows the isomerization reaction to more efficiently proceed.
Yamamoto et al. exemplifies sodium amide (NaNH2), as the metal compound in Examples 15-19 and 27, as well as NaH, Na and LiNH2 in Examples 29-32. See also Table 2 Yamamoto et al. exemplifies 1,4-BAC as the amine in examples 15-19 and 27. Yamamoto et al. exemplifies the aromatic aldehydes, 4-methylbenzaldehdye in examples 15-19, and cinnamaldehyde in example 27.
The exemplified ratio of sodium amide relative to the BAC amine is 1.28 mole % in examples 15-19. The exemplified ratio of sodium amide relative to the BAC amine is 2.69 mole % in example 27.
The exemplified ratio of 4-methylbenzaldehdye relative to the BAC amine is 1.2 mole % in examples 15-19. The exemplified ratio of cinnamaldehyde relative to the BAC amine is 2.34 mole % in example 27.
(abstract; paragraphs 2-5, 116-117, 129-130, 141, 144; Tables 1 and 2 and examples)
Ascertainment of the Difference Between Scope the Prior Art and the Claims
(MPEP §2141.012)
Yamamoto et al. is deficient in the sense that it does not exemplify applicant’s ratio of aldehyde to amine of 3.5 mol % to 10 mol %. Instead Yamamoto et al. exemplifies a ratio of aldehyde to amine of 1.2 mol % in examples 15-19 and 2.34 mole % in example 27.
Also Yamamoto et al. does not teach applicant’s elected species, the alicyclic amine, diaminodicylohexylmethane (R = CH2-Cyclohexyl, n = 0 in applicant’s Formula 1). Instead, Yamamoto et al. teaches the alicyclic amine, bis(aminomethyl)cyclohexane (BAC).
Okawa et al. teaches a process for isomerization of 1,4-BAC by utilizing a platinum catalyst to control the isomer amount and increase the trans isomer content. Okawa et al. also teaches that the alicyclic amine, bis(4-aminocyclohexyl)methane (or para-diaminodicylohexylmethane, the para isomer of applicant’s elected species), is also isomerized to increase the trans-trans amount, by using metal catalysts, or by using an imine, aldehyde and alkali catalyst. (abstract; column 1, lines 41-55)
Finding of Prima Facie Obviousness Rationale and Motivation
(MPEP §2142-2143)
However, it would be prima facie obvious to one of ordinary skill in the art at the time of the invention, for Yamamoto et al. to utilize a ratio of aldehyde to amine of 3.5 mol % to 10 mol %, since Yamamoto et al. teaches a preferred range of 0.20 to 5.0 mol %, which overlaps with applicant’s claimed range. Therefore, it would be obvious to optimize the ratio of aldehyde to amine and use a higher mol %, since Yamamoto et al. teaches that their ratio of aldehyde to amine range suppresses side reactions and improves yields, and thus is a result-effective variable.
It would also be obvious to substitute Okawa et al.’s bis(4-aminocyclohexyl)methane (or para-diaminodicylohexylmethane, the para isomer of applicant’s elected species), for Yamamoto et al.’s BAC, since both are alicyclic amines, and because Okawa et al. teach the equivalency of the alicyclic amines, which undergo similar isomerization reactions, in order to control the isomer amount. Thus, at the time of the instant invention, a person of ordinary skill in the art would have been motivated to substitute BAC for diaminodicylohexylmethane in Yamamoto et al.’s isomerization reaction, with a reasonable expectation of success. 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).
Response to Arguments
Applicant’s arguments have been considered but are not persuasive for the following reasons:
The examiner acknowledges applicant’s argument that a hindsight reconstruction was used and the equivalency teaching for acyclic amines was from the background art of Okawa.
The examiner does not agree with applicant’s arguments.
In response to applicant's argument that the examiner's conclusion of obviousness is based upon improper hindsight reasoning, it must be recognized that any judgment on obviousness is in a sense necessarily a reconstruction based upon hindsight reasoning. But so long as it takes into account only knowledge which was within the level of ordinary skill at the time the claimed invention was made, and does not include knowledge gleaned only from the applicant's disclosure, such a reconstruction is proper. See In re McLaughlin, 443 F.2d 1392, 170 USPQ 209 (CCPA 1971).
Also, with regard to the equivalency teachings for acyclic amines in the background art, the examiner contends that typically related inventions are specifically highlighted in the background section. Thus instead of undermining the equivalency teaching of acyclic amines, the background section specifically supports it. Furthermore, 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).
The use of alicyclic amines does not have to be absolutely identical in all their reagents, their effects or their function, but just recognized in the art for a similar purpose, which the background section highlights as isomerization of alicyclic amines.
The issue in the rejection is again not absolute equivalency of acyclic amines, but that there would be a reasonable expectation of success to substitute one acyclic amine for another. The examiner contends that there is a reasonable expectation of success, since the art teaches that the isomerization of acyclic amines are recognized in the art for a similar purpose.
The examiner acknowledges applicant’s argument that the reaction mechanism of applicant’s amine and Yamamoto’s amines are different. The applicant specifically highlights the two reaction mechanisms are different because the claimed amino group is directly bonded to the cyclohexane ring, whereas Yamamoto’s amine is bonded to a methylene group. Applicant also argues criticality of their molar ratio and mol %.
The examiner does not agree with applicant’s arguments. Because applicant has not provided factual support or evidence in the record for these two different mechanisms, the examiner interprets these reaction mechanisms as opinion and not as fact. Providing different mechanisms for the chemical transformation is hypothetical unless applicant provides substantiative evidence for the formation of different mechanistic intermediates and how this would impact the formation of the product.
Furthermore, applicant’s arguments are not commensurate in scope with the claims. Applicant’s independent claim 1 is drawn to a method of isomerizing an aliphatic diamine but does not claim the resulting isomerized product. Thus it is unclear how a different mechanism might impact product formation.
Additionally, applicant’s aliphatic diamine of Formula (I) includes two amines. One amine is bonded to the cyclohexane ring. The other amine is bonded to an R group. The R group reads on a methylene group. Since one of applicant’s amine can also be bonded to a methylene group, how would this be different than Yamamoto’s amine bonded to a methylene group? Thus applicant’s purported mechanism for isomerization of an amine bonded to a methylene group could also read on applicant’s amine of Formula (I).
Also, applicant’s arguments for criticality of the molar ratio and mol % are not commensurate in scope with the claims. Applicant’s claims are not limited to the critical range applicant’s argue. Applicant’s ranges are instead broadly claimed and thus it is unclear if applicant’s differences are unexpected as compared to the prior art.
Conclusion
No claim is 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 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.
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Jennifer Cho Sawyer
Patent Examiner
Art Unit: 1691
/RENEE CLAYTOR/Supervisory Patent Examiner, Art Unit 1691
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