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 .
Status of Claims
The examiner acknowledges the amendments to claims 16 and 23. Claims 15-19 are pending.
Priority
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Drawings
The drawings are objected to because Figures 7a and 7b are plots where multiple species properties are plotted. While the plot includes traces that are black and traces that are gray with accompanying shapes, the legend does not indicate which species the gray traces refer to, as all traces are shown as black. As such, it is not possible to determine which species are related to which trace. Corrected drawing sheets in compliance with 37 CFR 1.121(d) are required in reply to the Office action to avoid abandonment of the application. Any amended replacement drawing sheet should include all of the figures appearing on the immediate prior version of the sheet, even if only one figure is being amended. The figure or figure number of an amended drawing should not be labeled as “amended.” If a drawing figure is to be canceled, the appropriate figure must be removed from the replacement sheet, and where necessary, the remaining figures must be renumbered and appropriate changes made to the brief description of the several views of the drawings for consistency. Additional replacement sheets may be necessary to show the renumbering of the remaining figures. Each drawing sheet submitted after the filing date of an application must be labeled in the top margin as either “Replacement Sheet” or “New Sheet” pursuant to 37 CFR 1.121(d). If the changes are not accepted by the examiner, the applicant will be notified and informed of any required corrective action in the next Office action. The objection to the drawings will not be held in abeyance.
While the examiner notes that the applicant states that amended drawings have been submitted, these drawings do not appear to be present in the record.
Claim Objections
Claim 16 has been amended. As a result, the objection to claim 16 is withdrawn.
Claim Rejections - 35 USC § 112
Claim 23 has been amended and as a result, the prior 112(b) rejection has been withdrawn.
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 15-29 are rejected under 35 U.S.C. 103 as being unpatentable over Mees (Macromolecules (2015) volume 48 pages 3531-3538, Nonpatent Literature Reference #5 from IDS dated 7/10/2023) in view of Dargaville (Macromolecular Rapid Communications (2012) volume 33 pages 1695-1700).
Regarding Claims 15-18 and 24-25,
Mees teaches a polymer with a poly(2-alkyl-oxazoline backbone) with the following structure in scheme 1:
PNG
media_image1.png
142
164
media_image1.png
Greyscale
where R is an alkyl group (Page 3531, Introduction section, Paragraph 1) with methyl and ethyl groups mentioned (Page 3531, Introduction section, Paragraph 2) and with examples explicitly using R equal to ethyl (Page 3532, Experimental section, Paragraph 1). The structure from scheme 1 includes R1 groups such as propene (Table 1, Entry 10), meeting the requirements of the instant claim. The listed structure is generated from a 2-alkyl-2-oxazoline where R is equal to ethyl and where x=2, meeting the requirements of claims 17 and 18. Mees also teaches that terminal double and triple bonds are useful in post-polymerization modification reactions such as thiol-ene and other click reactions (Page 3531-2, Introduction section, Paragraph 3). Mees does not explicitly teach using this group for cross-linking. However, Dargaville teaches poly(2-oxazoline) polymers where pendant alkene groups are crosslinked with dithiol compounds in order to generate hydrogels (Abstract, Scheme 1). While Dargaville’s alkene is not connected through an amide linkage, it is connected to an oxazoline-based backbone unit and one of ordinarily skill in the art would recognize that other linkages would be possible. Also, because the cross-linking reaction proceeds in the presence of carbonyl functionality, it would logically follow that the presence of such a group does not hinder the cross-linking reaction. Seeking to adjust the length of the cross-linker to increase the rigidity of the polymer, the ordinarily skilled artisan would look to alternate groups appended to the base polymer to accomplish this. And as noted by Mees, the attachment of unsaturated groups is motivated to allow for post-polymerization modification (Page 3532, Introduction section, final paragraph). As such, it would have been obvious prior to the effective filing date of the instant application to have combined the cross-linking thiol-ene reaction used by Dargaville with the allylamido functionalized oxazoline-based polymer of Mees to obtain the predictable result of a cross-linked oxazoline-based polymer hydrogel with a reasonable expectation of success.
Finally, Mees in view of Dargaville teaches a method to generate the cross-linked polymer through mixing the alkene containing polymer with a dithiol in ethanol and irradiating the solution at 365 nm to generate a hydrogel (Page 1697, left column, paragraph 2).
Regarding Claims 19-21,
Mees teaches a copolymer with two different monomers as required by the instant claim as discussed above in regard to claims 15-18 and 24. Additionally, Mees teaches that 18% of the monomers are functionalized to have the allylamino side chains (Page 3533, Results and Discussion section, Paragraph 2), corresponding to a ratio of 18:82, meeting the requirement of the instant claims. Additionally, as 18% of the monomer units contain the allylamido group, it would logically follow that based upon a degree of polymerization of 100 (Page 3532, Experimental section, Paragraph 1), that 18 of the allylamino groups would be present, meeting the requirement of claim 21. Finally, as the structure of the polymer is the following:
PNG
media_image1.png
142
164
media_image1.png
Greyscale
the Z group is a succinimide-based linker, meeting the requirements for the structure according to claim 21.
Regarding Claim 22,
Mees teaches that the copolymer starting material has a degree of polymerization of 100 (Page 3532, Experimental section, Paragraph 1), which is further reacted to generate the desired copolymer, meeting the requirement of the instant claim.
Regarding Claim 23,
Mees disclosed a polymer with a degree of polymerization of 100, however does not disclose a polymer with a degree of polymerization of 200 to 500. However, Dargaville uses polymers with degrees of polymerization of greater than 200 (Scheme 1). As the degree of polymerization is defined to be the number of monomer units contained in the polymer, it would necessarily follow that a higher degree of polymerization would indicate a higher molecular weight of the polymer. Dargaville also teaches that the molar mass of the linear polymer chains is involved in determining the mesh size of the resulting hydrogel which is related to the size of molecule that can be encapsulated (Page 1698, right column, second paragraph). As such, the ordinarily skilled artisan would be motivated to adjust the mass of the polymer and by extension, the degree of polymerization, in order to accommodate the desired molecule to be encapsulated. It would therefore have been obvious prior to the effective filing date of the instant application to have set the degree of polymerization to a value necessary to fit the desired purpose of the polymer.
Regarding Claims 26 and 27,
Mees in view of Dargaville teaches the required structure of the instant claim as discussed above in regard to claims 15-18 and 24-25. Mees is silent on the use of the poly(2-oxazoline) polymers as inks. However, Dargaville teaches that hydrogels are useful in applications involving printed scaffolds (Page 1695, right column, paragraph 1) and additionally teaches the cross-linking reaction to take place in solvent as discussed above in regard to claims 15-18 and 24-25. It would necessarily follow that such a liquid could be dispensed and then cross-linked, which reads upon the requirements of the instant claim. It would have been obvious prior to the effective filing date of the instant application to have combined the cross-the teachings of Dargaville with the allylamido functionalized oxazoline-based polymer of Mees for the reasons discussed above in regard to claims 15-18 and 24-25.
Regarding Claims 28 and 29,
Claims 28 and 29 are directed towards a method of treatment of disorders or food or cosmetic products, but do not indicate any particular feature that is required to modify the composition in order to be suitable for such purposes. As such, these claims are treated as intended use and it would necessarily follow that any composition meeting the requirements of the composition would necessarily capable of serving in such capacities. Additionally, Mees states that poly(2-oxazoline) polymers are useful in biomedical applications (Page 3531, Introduction Section, right column, paragraph 1), which would include use cases such as for therapeutics as well as any use case that involves ingestion. As such, it would have been obvious prior to the effective filing date of the instant application to have used the composition of Mees in view of Dargaville as a method of administering therapeutics or in any biomedically related use case.
Response to Arguments
Applicant's arguments filed 3/30/2026 have been fully considered but they are not persuasive for the following reasons.
On pages 9 and 10, the applicant argues that there would be a lack of motivation to combine the references based upon the knowledge of reaction speed in the crosslinking. in response to applicant’s argument that there is no teaching, suggestion, or motivation to combine the references, the examiner recognizes that obviousness may be established by combining or modifying the teachings of the prior art to produce the claimed invention where there is some teaching, suggestion, or motivation to do so found either in the references themselves or in the knowledge generally available to one of ordinary skill in the art. See In re Fine, 837 F.2d 1071, 5 USPQ2d 1596 (Fed. Cir. 1988), In re Jones, 958 F.2d 347, 21 USPQ2d 1941 (Fed. Cir. 1992), and KSR International Co. v. Teleflex, Inc., 550 U.S. 398, 82 USPQ2d 1385 (2007).
Mees specifically points to the incorporation of terminal double and triple bonds for use in crosslinking using thiol-ene reactions as noted in the rejection and specifically is using an allyl group in some of the examples. While Mees does not teach the crosslinker, this deficiency is solved through the addition of Dargaville, which teaches the use of thiols for this purpose with related structures. While Dargaville is using longer linking chains between the unsaturation and the polymer backbone, Dargaville discloses the thiol-ene reaction and a specific linker that can be used, which the ordinarily skilled artisan would have motivation to use because Mees teaches that such reactions are useful in the polymer class and teaches polymers that can be used in this fashion. Further, as Mees specifically states that thiol-ene based crosslinking reactions are useful with polymers of the type taught, the ordinarily skilled artisan would have a reasonable expectation of success. Additionally, the rate of reaction is a limitation that does not appear in the claims and as such does not carry weight.
On page 11, the applicant argues that the references do not teach that the composition is a hydrogel. The examiner disagrees. Indeed, Dargaville is directed towards the synthesis of hydrogels and speaks to the degree of swelling in the abstract. While Mees does not directly speak to hydrogels, the combination of Mees and Dargaville teaches the composition required by the instant claims, and it would logically follow that the material would have the same properties. See MPEP 2144.05.I.
Also on page 11, the applicant states that Mees in view of Dargaville does not teach water solubility of the polymer. The examiner notes that this limitation does not appear in the claims. Further, as noted above, Mees in view of Dargaville teaches the composition as required by the claims and as such would logically have the same properties, regardless of whether the properties were mentioned.
In summation, the applicant’s arguments appear to focus on physical properties and a lack of motivation to combine the references. Based upon the explicit disclosure in Mees related to the crosslinking reaction as taught in Dargaville, the examiner disagrees and as to the physical properties, these limitations do not appear as claim limitations and further would logically follow the composition in the absence of evidence to the contrary. 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.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ADAM J BERRO whose telephone number is (703)756-1283. The examiner can normally be reached M-F 8:30-5.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Heidi Kelley can be reached at 571-270-1831. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/A.J.B./Examiner, Art Unit 1765
/JOHN M COONEY/Primary Examiner, Art Unit 1765
Prosecution Insights