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 .
Disposition of Claims
Examiner acknowledges the amendment to claim 1 and the addition of claim 22. Claims 1 and 4-22 are pending and claims 7-20 are withdrawn.
Claim Interpretation
Claim 1 is directed towards a polymer composition which further requires one of the components (polymacrolactone) to be generated through a reaction requiring a phosphazene base. This construction renders this claim to be a product-by-process claim. As such, the patentability of the claim is determined by the product (See MPEP 2113.I) and therefore, any process that generates the desired composition would read upon the claim.
Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claims 1, 4-6, and 21 are rejected under 35 U.S.C. 103 as being unpatentable over Shimoda (US 7,928,180) in view of Zotzmann (J. Mat. Sci. Mater. Med. (2011) volume 22, pages 2147-2154) and van der Meulen (Biomacromolecules (2008) volume 9, pages 3404-3410).
Regarding Claims 1, 4, and 21-22,
Shimoda teaches a biodegradable polymer containing imine bonds in the main chain structure (Column 6, Lines 14-19) which also contains polyesters formed from lactones (Column 7, Lines 19-35). Shimoda does not teach the use of macrolactones to form the polyester, though does state that ring opening polymerization may be used to form a polymer from lactones (Column 7, Lines 19-23). Zotzmann teaches the use of a polyester formed from pentadecalactone that is subsequently reacted with a diisocyanate to form a block copolymer with polycaprolactone (Scheme 1, Section 2.3). One of ordinary skill in the art, seeking to improve the resistance to hydrolysis as well as to improve the mechanical properties of the polymer would seek to substitute larger lactones, such as pentadecalactone, for smaller lactones such as caprolactone. Because caprolactone and pentadecalactone were demonstrated by Zotzmann to react with a diisocyanate to form a block copolymer, it would have been obvious to have substituted a polymer from a macrolactone such as pentadecalactone for a smaller lactone such as caprolactone as used by Shimoda to obtain the predictable outcome of a biodegradable polyester from a macrolactone with a reasonable expectation of success.
Shimoda in view of Zotzmann teaches the use of macrolactones such as pentadecalactone to form biodegradable polyesters that are incorporated into a doubly degradable polymer containing imine bonds, but does not teach the use of polylactones such as polyglobaltide, polyhexadecalactone, or polyambrettotide that are synthesized using a phosphazene base. As noted however, because the claim is a product-by-process claim, any method that generates the desired product would read upon the claim. van der Meulen teaches the synthesis of polymers made from pentadecalactone, hexadecalactone, globaltide, and ambrettotide using Candida Antarctica lipase B (CALB) (Page 3404, right column, second paragraph) and notes that using CALB as the polymerization catalyst not only yields higher molecular weight polymer, but also proceeds more quickly and affords polymer free of metal contamination (Page 3404, right column, second paragraph) and additionally teaches that polyesters made from larger lactones such as pentadecalactone offer polyesters with properties similar to that of low density polyethylene (Page 3404, right column, paragraph 1), providing the ordinarily skilled artisan with motivation to incorporate such materials made using enzymatic synthesis for more environmentally friendly biodegradable polymers with properties similar to those of non-biodegradable counterparts. As such, it would have been obvious prior to the effective filing date of the instant application to have combined the polymacrolactone teachings of Zotzmann with the use of lipase-mediated polymerization as taught by van der Meulen to generate a metal-free polymacrolactone for use in the doubly-degradable polymer taught by Shimoda to yield the predictable result of a doubly-degradable polymer containing a polymacrolactone with a reasonable expectation of success.
With regard to the selection of phosphazene base, as claim 1 is a product-by-process claim, that renders the base used to generate the polymacrolactone to be an optional component absent a showing of a material difference in the generated polymacrolactone.
Regarding Claim 5,
Shimoda teaches that the biodegradable polymer contain the following unit:
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54
218
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in which Y1 and Y2 are both imines (Column 4, Lines 22-36) and all R groups representing hydrocarbons, meeting the requirement of the instant claim.
Regarding Claim 6,
Shimoda does not discuss whether the material generated is a dynamer, However, a dynamer, as defined by applicant in the specification is “a constitutional dynamic polymer. Constitutional dynamic polymers are polymers whose monomeric components are linked through reversible connections”. Imine formation is inherently reversible, returning to a carbonyl compound and an amine under certain conditions, which are free to then react again, meeting the applicant’s definition. Thus, owing to the closeness of make-ups it is seen that the materials generated would inherently be dynamers as claimed. Shimoda discloses a polymeric polyester compound containing multiple imine bonds. It has been held that “When the PTO shows a sound basis for believing that the products of the applicant and the prior art are the same, the applicant has the burden of showing that they are not." In re Spada, 911 F.2d 705, 709, 15 USPQ2d 1655, 1658 (Fed. Cir. 1990). See MPEP 2112.01.I.
Response to Arguments
Applicant's arguments filed 9/17/2025 have been fully considered but they are not persuasive for the following reasons.
On page 6, the applicant states that the catalyst imparts distinct structural characteristics. However, the applicant does not provide any evidence for a structural difference. As the examiner in the rejection has presented art showing the generation of the polymacrolactone, the burden is thus on the applicant to demonstrate this difference (See MPEP 2113.II).
In total, the applicant’s amendments and arguments are directed towards the use of the phosphazene superbase in forming the polymacrolactone. On the basis of the claim construction of claim 1 being a product-by-process, in the absence of a demonstration otherwise, the method of generation of the polymacrolactone would not be expected to have an effect on the final composition. As a result, the rejection is maintained.
Conclusion
THIS ACTION IS MADE FINAL. 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.
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/A.J.B./Examiner, Art Unit 1765
/JOHN M COONEY/Primary Examiner, Art Unit 1765