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 .
Claim Status
Claims 1 and 57 were amended, claims 2, 12-14, 23-28, and 59-61 were canceled, and claims 62-70 were newly added in the response filed 6/29/2026. Claims 1, 3-10, 57, 58, and 62-70 are pending. Claims 1, 3-9, 57, 58, 62, 65, 66, and 68-70 are allowed. Claims 10, 63, 64, and 67 are rejected.
New Claim Rejections - 35 USC § 112(a)-New Matter
The following is a quotation of the first paragraph of 35 U.S.C. 112(a):
(a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.
The following is a quotation of the first paragraph of pre-AIA 35 U.S.C. 112:
The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor of carrying out his invention.
Claim 67 is 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.
New claim 67 was introduced which recites “the process of claim 57, wherein the purity of the diisocyanate after step (vi) is >99%”. The Applicant indicates at the top of p. 1 of the response that the new claims are fully supported by the application as originally filed, but provides no specific citations for said claims. The Examiner cannot find where the limitations of new claim 67 are supported in the specification as filed. The rest of the new claims appear to be supported by the first three entries of Table 1 in [0183] and their corresponding experimental procedures and/or [0087] of the specification as filed. Also see MPEP 2163.06: “When an amendment is filed in reply to an objection or rejection based on 35 U.S.C. 112(a) or pre-AIA 35 U.S.C. 112, first paragraph, a study of the entire application is often necessary to determine whether or not "new matter" is involved. Applicant should therefore specifically point out the support for any amendments made to the disclosure.”
New Claim Rejections - 35 USC § 112(b)
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
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.
Claims 10, 63, and 64 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Claim 10 recites the limitation "wherein step (v) comprises heating the third solution in flow …". There is insufficient antecedent basis for this limitation in the claim. It appears that this limitation should recite “step (iv)” instead of “step (v)” based on the most recent amendments to claim 1.
Claim 63 recites “wherein the diisocyanate is generated at a rate of at least 0.5 g h-1 (41 mmol/hr)”. It is not clear how the value in the parentheses in mmol/hr is related to the rate in g h-1. Are they supposed to be equivalent or are they alternatives to one another? If the former is intended, it would appear as if the limitation only applies to a specific compound of a particular molecular weight for which this relationship would hold true, and this information is missing from the claim, thus making it indefinite. If the latter is correct, then this is not clear from the present claim language.
Claim 64 has the same issue with respect to the limitation “8.5 gh-1 (70 mmol/hr)”.
Withdrawn Claim Rejections - 35 USC § 103
Regarding the rejection of record of claim(s) 1-10, 12-14, 23-28, and 57-61 is/are rejected under 35 U.S.C. 103 as being unpatentable over Sprecher (“Acyl Azide Synthesis and Curtius Rearrangements in Microstructured Flow Chemistry Systems” J. Flow Chem. 2012, p. 20, of record in the IDS filed on 9/14/2022, of record) in view of Rumi (“Adaptation of an Exothermic and Acylazide-Involving Synthesis Sequence to Microreactor Technology” Org. Proc. Res. Dev., 2009, p. 747, of record), Balci (“Acyl Azides: Versatile Compounds in the Synthesis of Various Heterocycles” Synthesis, 2018, 50, p. 1373-1401), Britton (“The assembly and use of continuous flow systems for chemical synthesis” Nature Protocols, 12, 2017, p. 2423) and Saito (US2011/0052953, published on 3/3/2011) on p. 2-16 of the OA dated 2/3/2026, the Applicant’s arguments on p. 3-6 of the response have been fully considered and are persuasive.
Applicant has amended the scope of the independent claims to be limited to producing diisocyanates of formula O=C=N-L1-(L2)m-(L3)n-N=C=O, wherein L1, L2, and L3 are each independently C1-C12 alkylene, m is 0 or 1, and n is 0. Applicant argues the primary reference Sprecher does not teach or suggest this limitation, being directed to a cyclohexenyl diisocyanate or phenyl isocyanate. Neither of these correspond to the aliphatic saturated diisocyanates claimed. Nor is this deficiency cured by any of the other cited references. Applicant also argues that there would be no expectation of success of modifying Sprecher to arrive at the claimed process because of the differences between the structures shown in Sprecher and that claimed. Further, the skilled artisan would not expect the good yields that are obtained from the instant reaction (70% or higher, as evidenced by the first three entries of Table 1 in [0187] of the specification as filed). Applicant teaches in Sprecher, only 49% of the final diamine (4) (going a step past the diisocyanate intermediate) is obtained. These arguments are persuasive; therefore, the rejection of record is withdrawn.
Allowable Subject Matter
Claims 1, 3-9, 57, 58, 62, 65, 66, and 68-70 are allowed. Claims 10, 63, 64, and 67, rejected under 35 USC 112 above, also appear to be free from the prior art.
The following is a statement of reasons for the indication of allowable subject matter: the claimed method is distinguished from the closest prior art for the reasons set forth above.
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 AMY C BONAPARTE whose telephone number is (571)272-7307. The examiner can normally be reached 11-7.
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/AMY C BONAPARTE/Primary Examiner, Art Unit 1692
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