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 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 (i.e., changing from AIA to pre-AIA ) 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, 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.
Claims 1-4 and 6-11 are rejected under 35 U.S.C. 103 as being unpatentable over US Pub. No. 2010/0101455 to Burckhardt in view of WO 2020/030607 to Schlumpf, with USPN 12,209,157 cited as the English equivalent.
Regarding claims 1-4 and 6-11, Burckhardt teaches aldimines and compositions comprising aldimines particularly suitable as latent hardeners in curable compositions, particularly compositions comprising one or two-component isocyanate groups and polyurethane compositions (Burckhardt, Abstract, paragraph 0007). Burckhardt teaches that the composition is moisture-curing (Id., paragraphs 0227-0264). Burckhardt teaches that aldimines are usually room temperature liquid compounds (Id., paragraph 0006). Burkhardt teaches that the curable compositions comprise aldimines and/or aldimino containing compounds, which are reaction products of the aldimines (Id., paragraphs 0008-0009). Burckhardt teaches various aldimines of the formulas (I), (II), (Ia), (IIa), and (Ib) (Id., paragraphs 0012-0059) formed by the reaction of an amine and an aldehyde (Id., paragraph 0064). Burckhardt teaches that examples of preferred amines include bis(4-aminocyclohexyl)methane (Id., paragraph 0109), and that preferred aldehydes includes 2,2-dimethyl-3-(N-morpholino) propanal (Id., paragraphs 0102, 0224). Note that Applicants’ specification at page 8 lines 14-16 and 27-29 recite similar amines and aldehydes to form the claimed aldimine. Therefore, it is reasonable for one of ordinary skill in the art to expect that the aldimine product is within the scope of the claimed aldimine.
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to make the moisture-curing composition of Burckhardt, and forming the aldimine as claimed from bis(4-aminocyclohexyl)methane and 2,2-dimethyl-3-(N-morpholino) propanal, motivated by the desire of forming a conventional aldimine compositions formed from preferred precursors based on the totality of the teachings of Burckhardt.
Burckhardt teaches forming a polyurethane from a polyol and an isophorone diisocyanate (Burckhardt, paragraph 0420). Burckhardt does not appear to teach the claimed content of monomeric isophorone diisocyanate. However, Schlumpf teaches a similar blocked amine as a curing aid for polymers containing isocyanate groups, obtained from the reaction of at least one monomeric diisocyanate with at least one polyol in an NCO/OH ratio of at least 3/1, and the moisture-curing polyurethane compositions obtained (Schlumpf, Abstract). Schlumpf teaches that the polymer containing isocyanate groups has a monomeric diisocyanate content of not more than 0.5% by weight, preferably no more than 0.2% by weight (Id., column 3 lines 39-48, column 4 lines 39-47), an NCO content in the range from 0.5% to 10% by weight (Id., column 4 lines 51-54) and at least one diol, such as a polyether polyol, having an OH number especially in the range from 56 to 150 mg KOH/g (Id., column 4 lines 55-65, column 6 lines 1-57). Schlumpf teaches that monomeric diisocyanate is removed in a separation method, preferably a distillative method (Id., column 7 lines 1-14). Schlumpf teaches that suitable monomeric diisocyanates include preferably isophorone diisocyanate (IPDI) (Id., column 5 lines 12-49). Schlumpf teaches that moisture-curing polyurethane compositions having a low monomeric diisocyanate content cure reliably and rapidly to give elastic materials having low residual tack and excellent stability to weathering influences when blocked amines are used as curing aids (Id., column 5 lines 28-61). Schlumpf teaches that the blocked amines preferably have at least one aldimino group (Id., column 8 lines 22-25).
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to make the composition of Burckhardt, wherein the polyurethane comprises the moisture-curing polyurethane composition of Schlump, including the claimed structure and composition, motivated by the desire of forming a conventional moisture-curing polyurethane composition which predictably reacts with aldimines to cure reliably and rapidly while having low residual tack and excellent stability to weathering influences when blocked amines are used as curing aids.
Regarding claims 1, 9, and 10, the prior art combination teaches various suitable aldimines wherein the curable composition necessarily comprises at least one aldimine (Burckhardt, paragraph 0139-0141, 0238). Since the prior art combination teaches various aldimines including aldimines formed as set forth in Applicants’ specification, it is reasonable for one of ordinary skill to expect that additional aldimines, such as isomers or as claimed, are functionally equivalent and similarly suitable for the invention of the prior art combination. Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to make the composition of the prior art combination, wherein the composition additionally includes different aldimines or isomers as claimed, such as in the claimed amounts including less than 35% of the trans,trans isomer, motivated by the desire of forming a conventional moisture-curing polyurethane composition comprising a combination of aldimines based on the desired amount of reaction suggested by Burckhardt.
Regarding claims 2-4, since the prior art combination renders obvious the claimed aldimine, it is reasonable for one of ordinary skill to expect that the aldimine is a liquid at 23ºC, and that the aldimine comprises the claimed structure.
Regarding claims 8 and 11, the prior art combination teaches that the composition includes at least one filler or oligomeric polyisocyanate such as IPDI (Burckhardt, paragraph 0289; Schlumpf, column 15 lines 36-55).
Response to Arguments
Applicants’ arguments filed March 16, 2026, have been fully considered but they are not persuasive. Applicants argue that Burkhardt merely teaches bis-(4-aminocyclohexyl)-methane in a laundry list of possible amines for reacting with an aldehyde to produce the aldimine. Additionally, Applicants argue that none of the Examples or embodiments disclosed in Burkhardt uses bis-(4-aminocyclohexyl)-methane in combination with 2,2-dimethyl-3-(N-morpholino)-propanal.
Regarding Applicants’ arguments, Examiner respectfully disagrees with the characterization of Burkhardt, which shares the same assignee and inventor as the current application. As set forth above, Burkhardt teaches that both bis-(4-aminocyclohexyl)-methane and 2,2-dimethyl-3-(N-morpholino)-propanal are preferred.
Applicants argue that as shown in the examples of Schlumpf, the compositions combining the polymers having low monomeric diisocyanate with a blocked amine have inferior mechanical properties, particularly in terms of the modulus of elasticity, whereas the Examples in the present application surprisingly exhibit a high modulus of elasticity even though the total content of monomeric diisocyanate is low, as shown in Table 1. Therefore, Applicants argue that the improvement of mechanical properties, especially modulus of elasticity, surface tackiness, and curing time, would have been unexpected over the teachings of the applied references.
Regarding Applicants’ arguments, Examiner respectfully disagrees. Applicants do not claim any properties associated with improvement of mechanical properties, especially modulus of elasticity, surface tackiness, or curing time. Therefore, Applicants’ arguments are not commensurate in scope with the claimed invention.
Additionally, Applicants’ reliance on Table 1 of Schlumpf does not differentiate the claimed invention from the invention of the prior art combination, as Schlumpf alone is not relied on to teach properties which are not claimed. Additionally, note that the compositions relied on in Table 1 of Schlumpf are not relied on to be within the scope of the claimed composition, nor do Applicants establish that the invention of the prior art combination would not similarly comprise substantially similar properties once formed. Additionally, Schlumpf similarly teaches that after the curing the moisture-curing polyurethane has high elasticity and extensibility, high strength, and low residual tack (see Schlumpf at column 3 lines 18-32; Applicants’ specification at Abstract). Therefore, Applicants’ arguments do not distinguish the claimed invention from the invention of the prior art combination.
Conclusion
Applicants’ amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicants are 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 PETER Y CHOI whose telephone number is (571)272-6730. The examiner can normally be reached M-F 9:00 AM - 3:00 PM.
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/PETER Y CHOI/Primary Examiner, Art Unit 1786
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