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
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 1-5 are rejected under 35 U.S.C. 103 as being unpatentable over Gridnev, WO 2011/079041.
Applicant is directed to paragraph [0056] where a genus of triamine compounds are disclosed in terms of formula (IV) with the concomitant description of variables. In paragraph [0059], there are disclosed approximately 30 permutations of the triamines conforming with prior art formula (IV), none of which, it is conceded, are anticipatory of the aliphatic polyamines encompassed within formula (I) of claim 1. At the same time, it is observed that (i) in every single exemplification but one, Ra is a hydrogen atom such that both terminal amine moieties are primary amines like in the claimed polyamines, and (ii) in the vast majority of instances where a group Rc is present, that group is a methyl group, consistent with the branched linking groups of the claimed polyamines. In six of the exemplifications, both linkers between amine nitrogen atoms are branched and the pendant groups are methyl or can be methyl in all cases. The one way in which those six differ is that they are symmetrical insofar as they contain the same number of carbon atoms per linking group and the pendant methyl group is attached to the same carbon atom in each. By contrast, the claimed tri- and tetraamine compounds are asymmetric in that one of the branched linking residues is a C4 linker whereas the remaining linking groups are branched C3 alkylene groups.
MPEP 2144.08 provides guidance as to how genus-species situations should be evaluated. Among the criteria to be considered are the size of the genus, structural similarity, suggestion of similar properties, etc. The size of the genus is fairly small in the Examiner’s estimation, especially upon noting that Ra is generally always a hydrogen atom and it is apparently preferable that R3 be a methyl group. This in combination with the fact that “n” and “m” are both equal to 1 to 4 means that there are only 16 unique embodiments where assignment of values to “n” and “m” are concerned (n=1/m=1, n-1/m=2 and so on) and, there are effectively only 10 distinct combinations of values of n and m where both contain a methyl substituent because a compound where, for instance, n=1 and m=3 would be indistinguishable from one where m=1 and n=3.
Further, prior art embodiments where a branching moiety is a methyl group are “typical” since the vast majority of those containing branching groups among the prior art exemplifications have methyl branches. This is also true of the claimed aliphatic polyamines given that structures listed in association with “A” and “Q” all possess methyl branches.
The prior art triamines are used in an entirely different capacity than are those claimed so a conclusion of obviousness is admittedly not aided by this consideration. Nevertheless, it is the Examiner’s opinion that there are sufficiently few of the prior art triamines when one takes into account the obviously favored embodiments of Ra and Rc and the relatively few distinct combinations of “m” and “n” that a polyamine
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where n=0 and A and Q are as defined would have been obvious to one of ordinary skill as of the effective filing date of the invention.
As an aside, the Examiner has considered whether or not Applicants’ disclosure contained data illustrative of unexpected results that would have invalidated this rejection but did not perceive that a convincing showing had been made. According to the bottom of page 2 of the instant Specification, an objective of the invention was to identify polyamine curatives that, when reacted with epoxy resins would facilitate a longer pot life, lower viscosity of the mixture, a high glass transition temperature, and low brittleness. Of the three inventive examples summarized in Table 1, only Example 1a even reported a Charpy value (reflective of impact strength, which is the opposite of brittleness). The Examiner notes that the epoxy resin crosslinked with TMTETA compares favorably with IPDA where viscosity and Tg are concerned and, while the pot life is admittedly lower, the Charpy of the resulting crosslinked epoxy is higher meaning that it has better impact strength so the polyamine of Ex 1a hardly is demonstrated as yielding a crosslinked epoxy with uniformly superior properties. No other comparisons are even as meaningful as this one to the extent that neither of Ex 1b and Ex 1c even recite a Charpy measurement. (It is noted that IPDA compares favorably with Ex 1b in terms of pot life, viscosity, and glass transition temperature.
Allowable Subject Matter
Claims 6-7 and 9-13 are objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims. To reiterate, the prior art polyamines are employed in a different capacity (precursors for making polycyclic guanidine compounds) than in the instant invention (curing agents for epoxy resins). To the extent that the claimed polyamines of claim 1, and especially claims 3 to 5, are not anticipated by Gridnev, there is, of course, no indication of a synthetic approach for making any of these nor could the Examiner find evidence that the methods outlined in claims 11-13 had been documented previously.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to MARC S ZIMMER whose telephone number is (571)272-1096. The examiner can normally be reached M-F 8:30-5:00.
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September 30, 2026
/MARC S ZIMMER/Primary Patent Examiner, Art Unit 1765
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