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 .
Applicant’s amendment dated 11 September 2025 is hereby acknowledged. Claims 1-13 as amended are pending. All outstanding objections and rejections made in the previous Office Action, and not repeated below, are hereby withdrawn.
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior office action.
New grounds of rejection set forth below are necessitated by applicant’s amendment filed on 11 September 2025. For this reason, the present action is properly made final.
Claim Rejections - 35 USC § 102
Claim(s) 1-8 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Owji et al., “Synthesis, Characterization, and 3D Printing of an Isosorbide-Based, Light-Curable, Degradable Polymer for Potential Application in Maxillofacial Reconstruction,” ACS Biomater. Sci. Eng. 6, 2578-2587 (2020) (“Owji”).
This article published October 2, 2019.
As to claims 1-3 and 5-8, Owji teaches the reaction scheme:
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(p. 2580). The resulting compound is a reaction product of ethylene oxide adduct of isosorbide, specifically isosorbide adducted with one ethylene oxide unit at each hydroxyl group, as required by claims 1-3, with isophorone diisocyanate as required by claims 1 and 5, followed by reaction with hydroxyethyl methacrylate as required by claims 1 and 6. The resulting compound meets the formula 2 of claims 7 and 8, where M is an isosorbide residue, each R1 is ethylene, each R2 is a cycloalkylene group, each R3 is an alkylene group, each R4 is methyl, each of m and n is 1, and m + n is 2 as required by claims 7 and 8. Owji does not speak to the hydrophilicity, but the compound is the same as recited, and therefore is presumed to be hydrophilic.
As to claim 4, Owji does not teach forming the ethylene oxide adduct by the recited method. However, this limitation is interpreted as a product by process limitation, for which patentability is determined by the end product. See MPEP 2113. Since the compound is the same as recited, it is presumed to be the same as produced by the recited process.
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.
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 9 is rejected under 35 U.S.C. 103 as being unpatentable over Owji et al., “Synthesis, Characterization, and 3D Printing of an Isosorbide-Based, Light-Curable, Degradable Polymer for Potential Application in Maxillofacial Reconstruction,” ACS Biomater. Sci. Eng. 6, 2578-2587 (2020) (“Owji”) in view of KR 20170136069 A (“Im”).
A partial machine translation of KR 20170136069 A is enclosed.
As to claim 9, Owji teaches the reaction scheme:
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(p. 2580). The resulting compound is a reaction product of ethylene oxide adduct of isosorbide (compare starting material structure to compound to ethylene oxide adduct taught by Formula 1 of the specification), with isophorone diisocyanate to form an isocyanate functional intermediate, followed by reaction with hydroxyethyl methacrylate. Owji does not speak to the hydrophilicity, but the compound is the same as recited, and therefore is presumed to be hydrophilic.
Owji does not teach reacting isosorbide with ethylene oxide to arrive at the ethylene oxide adduct. However, it is known that this same isosorbide-ethylene oxide adduct may be obtained by reacting ethylene oxide with with the two hydroxyl groups of isosorbide, as taught by Im, para. 0016, showing same structure as shown in Owji. As such, the use of this method to provide the same starting material is an obvious modification shown to be suitable for forming the starting material by Im.
Double Patenting
Claims 1-3 and 7 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 2, 3, and 6 of copending Application No. 18/277,468 (reference application). Although the claims at issue are not identical, they are not patentably distinct from each other because copending claim 2 includes the urethane from the components as recited by claims 1 and 2. It is presumed to have hydrophilicity, being the same components. Copending claim 3 adds the recited anhydrosugar of claim 3. Copending claim 6 recites the same structure as claim 7, where it can be seen the anhydrosugar alcohol has been adducted with alkylene oxide on both ends.
Claims 1-3, 7 and 8 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 3, 4, 7 and 8 of copending Application No. 18/292,052 (reference application). Although the claims at issue are not identical, they are not patentably distinct from each other because copending claim 3 includes the hydrophilic (meth)acryl modified polyurethane from the components as recited by claims 1 and 2. It is presumed to have hydrophilicity, being the same components. Copending claim 4 adds the recited anhydrosugar of claim 3. Copending claim 7 recites the structure of claim 7, which is shown to have an anhydrosugar that has been adducted at both ends with alkylene oxide, urethane units deriving from isocyanate, and acrylate units derived from hydroxyalkyl (meth)acrylate. Copending claim 8 recites the additional features of claim 8.
Claims 5 and 6 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claim 7 of copending Application No. 18/292,052 in view of Owji et al., “Synthesis, Characterization, and 3D Printing of an Isosorbide-Based, Light-Curable, Degradable Polymer for Potential Application in Maxillofacial Reconstruction,” ACS Biomater. Sci. Eng. 6, 2578-2587 (2020) (“Owji”).
As to claims 5 and 6, copending claim 7 recites the structure of claim 7, which is shown to have an anhydrosugar that has been adducted at both ends with alkylene oxide, urethane units deriving from isocyanate, and acrylate units derived from hydroxyalkyl (meth)acrylate. Copending claim 7 does not recite the polyisocyanate of claim 5 or the hydroxyalkyl (meth)acrylate of claim 6. However, Owji teaches a similar urethane methacrylate based on ethylene oxide adduct of isosorbide, using isophorone diisocyanate and 2-hydroxyethyl (meth)acrylate (p. 2580). Owji teaches this product is suitable for tissue repair, and as such, the use of these in conjunction with the recited adduct of anhydrosugar is an obvious modification.
Allowable Subject Matter
Claims 10-13 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.
The following is a statement of reasons for the indication of allowable subject matter: the closest prior art, the Owji reference cited above, teaches the recited acryl modified urethane resin, but there is no suggestion in Owji or other prior art to form a waterborne coating composition as required by claims 10 and 13. The claims are allowable over the copending claims of US App. Nos. 18/277,468 and 18/292,052.
Response to Arguments
While new grounds of rejection are set forth above, the following discussion is given in response to those arguments of applicants that still apply to references or rejections over references that are being carried over from the preceding action. Arguments pertaining to any reference or rejection not being carried over are rendered moot and need not be addressed.
Applicant's arguments filed 11 September 2025 have been fully considered but they are not persuasive.
Applicant argues against the Owji reference on the grounds that Owji teaches a different synthetic method for obtaining the ethylene oxide adduct of sugar alcohol. This is not persuasive, because the resulting compound is identical to that obtained by reacting the hydroxyl groups of isosorbide with ethylene oxide, and therefore the specific process used to form the starting material does not make the claims patentable. Moreover, even if claiming the process, this does not result in a patentable distinction, since it is known in the art to make the same starting compound of Owji by the recited method of claim 9, as shown by the Im reference.
Applicant's arguments with respect to the non-statutory double patenting rejections are not persuasive. While the copending claims are directed to compositions, each of these disclose the same polyurethane as now claimed, as set forth above, and therefore meet the limitations thereto, even if ultimately directed to specific compositions containing the recited polyurethane.
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 KREGG T BROOKS whose telephone number is (313)446-4888. The examiner can normally be reached Monday to Friday 9 am to 5:30 pm.
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/KREGG T BROOKS/ Primary Examiner, Art Unit 1764