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 .
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 3/17/2026 has been entered.
Priority
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Status of Claims
The examiner acknowledges the amendments to claims 16 and 19 as well as the cancellation of claims 17 and 18. Claims 1-15 were previously canceled. Claims 16 and 19-31 are pending.
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 16 and 19-31 are rejected under 35 U.S.C. 103 as being unpatentable over Hasson (US 2009027754) as evidenced by Steinmann (US 6,165,408).
Regarding Claims 16 and 20,
Hasson teaches macro-diacrylates and polyacrylates that have shape-memory properties (Abstract) which can have a backbone made from a variety of macrodiols and polyols, including lactic acid (Paragraph 37) and has the following structure:
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In which R1 is a macrodiol, R2 is a diisocyanate, R3 is H or low alkyl (such as methyl), R4 is alkyl of 2 to 10 carbons, and m can be any integer from 0 to 10 (Paragraph 32), with the above structure containing at least 2 crosslinkable functionalities, meeting the requirements of the instant claims. Acrylates are polymerizable, and thus meet the requirement of crosslinkable end-capping groups and diisocyanates upon reaction with alcohols will yield urethane bonds as shown in the structure above. While Hasson does not teach the use of oligoethers to link the acrylate or methacrylate to the polymer backbone, the use of such groups is recognized in the art to be equivalent with alkylene linkers as evidenced by Steinmann, which uses structures of the following structure:
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in which R3 is hydrogen or methyl (Column 5, Lines 28-29) and where B1 can be an alkylene radical of 1 to 4 carbons (Column 5, Lines 33-41) or alternatively an alkylene interrupted with oxygen atoms (Column 5, Lines 56-63) which represent oligoethers. As Steinmann teaches the use of alkylene and oligoether linkers to be equivalents used for the same purpose, it would have been obvious prior to the effective filing date of the instant application to have substituted oligoethers for alkylene groups to link the acrylate or methacrylate to the polymer backbone. See MPEP 2144.06.II.
With regard to the crystallinity, Hasson teaches that the polyacrylate polymers can be amorphous (Paragraph 78).
Regarding Claim 19,
Hasson teaches the general structure of the instant claims as discussed above in regard to claim 16. Group Y of the instant claims is represented above as R4, with R2 and the carbamates on either side equivalent to Z of the instant claims. X is the acrylate termination group.
Regarding Claim 21,
Hasson teaches that polymers of lactic acid and containing lactic acid can be used (Paragraph 37).
Regarding Claim 22,
Hasson teaches the use of polyesters made from lactic acid (Paragraph 37). While Hasson doesn’t explicitly state the glass transition temperature (Tg) of such polymer backbones, the Tg of polylactic acid would be higher than -20 °C, meeting the requirement of the instant claim.
Regarding Claim 23,
Hassan teaches an acrylate end-capped polyurethane containing polymer, but does not explicitly speak to the end-capping content. However, Hasson does teach that it is most preferred to have macro-polyol urethane acrylates of molecular weight between 5,000-20,000 (Paragraph 57). A polymer of molecular weight of 5,000 with 2 acrylate end-capping groups would have a value of 0.4 mmol/g, or alternatively, a polymer of molecular weight of 10,000 with 4 acrylate end-capping groups would have an identical value, meeting the requirement of the instant claim.
Regarding Claim 24,
Hasson teaches that the polymer is most preferred to be of a molecular weight of between 5,000 and 20,000 (Paragraph 57).
Regarding Claim 25,
Hasson teaches that a variety of polyhydroxyl compounds may be used, including pentaerythritol (Paragraph 41), which when used would result in a star polymer with 4 arms.
Regarding Claim 26,
Hasson teaches that the polymer can be crosslinked onto materials such as wires and fibers (Paragraph 87). While the size of the fibers or wires is not disclosed, sufficiently small examples of such materials would act to dilute the composition without reacting with the polymer. Because such components are known to increase the strength of the polymers that contain them, one of ordinary skill in the art, seeking to improve the strength of the resulting crosslinked composition, would look to add such materials in order to accomplish this goal. Therefore, it would have been obvious prior to the effective filing date of the instant application to have added non-reactive materials such as a fiber to the composition to obtain the predictable result of a strengthened crosslinked material.
Regarding Claims 27, 28, 29, and 30,
Hasson teaches that the polymers can be crosslinked thermally through a free radical reaction using reagents such as di-tert-butyl peroxide, azobisisobutyronitrile (Paragraph 77) or through UV irradiation using a photoinitiator (Paragraph 76). Additionally, Hasson teaches crosslinking such materials in the absence of diluent as described in Paragraphs 85 and 86.
Regarding Claim 31,
Hasson teaches a polymer that can be crosslinked, however does not teach that it can be shaped using additive manufacturing. Additive manufacturing, which is generally used to refer to 3-dimensional (3D) printing, can be conducted with polymers in a melted state that harden after being dispensed. A composition that can be dispensed in a molten state that contains a photoinitiator could thus be 3D printed and subsequently exposed to the correct wavelength of light to initiate the crosslinking reaction to give the final product. Hasson teaches a composition of the acrylate containing polymer with a photoinitiator that is heated and coated onto a glass plate and subsequently crosslinked using UV irradiation (Paragraphs 85 and 86). One of ordinary skill in the art, seeking to generate a complex structure generated out of a shape-memory material, would look to create that structure using an additive manufacturing technique such as 3D printing. Because the material as disclosed by Hasson is capable of being used in the steps required for such an operation, it would have been obvious to have used the composition as taught by Hasson in an additive manufacturing process to obtain the predictable result of a complex structure made of a shape-memory material with a reasonable expectation of success.
Response to Arguments
Applicant's arguments filed 3/17/2026 have been fully considered but they are not persuasive for the following reasons.
On pages 5 and 6, the applicant argues that Hasson fails to teach the use of oligoethers to link the acrylate or methacrylate to the polymer chain and therefore Hasson fails to teach or suggest each element. The rejection has been amended to address the applicant’s amendment adding this limitation and this point has been addressed in that rejection.
On page 7, the applicant argues that Hasson fails to teach the use of additive manufacturing. While the examiner agrees that Hasson does not explicitly teach the use of additive manufacturing, Hasson does teach that such materials are given their permanent shape using conventional processing methods (Paragraph 7). As the properties of the composition do not depend upon the method by which the composition is shaped, the method of shaping does not impose a meaningful limitation upon the composition itself and further, additive manufacturing would be interpreted by the ordinarily skilled artisan to be included in conventional processing methods and thus its use to shape such a material would be obvious.
Finally, on pages 7 and 8, the applicant argues that the use of oligoethers as a method of tuning the shape-memory polymer. The examiner does not disagree. While the examiner appreciates the affidavit filed by the applicant speaking to the differences between the use of alkylene and oligoether linkers for attaching the (meth)acrylate groups to the polymer, as noted in the rejection, these groups have been taught in the prior art to be used for equivalent purposes and as such, the benefits of using one linker over the other is not relevant as to whether it would be obvious to use the oligoether. As both alkylene and oligoether groups have been used in the prior art for this purpose it would remain obvious to the ordinarily skilled artisan to substitute one for the other, regardless of the benefits in material properties observed by the applicant. Further, the properties that the applicant states in the affidavit to be improved by using oligoether linkers in place of alkylene linkers do not appear as limitations in the claims and as such, are not considered persuasive.
In summary, the use of oligoether linkers to connect acrylates and methacrylates to urethane-based polymer backbones is known in the art to be equivalent to the use of alkylene linkers, rendering their use in this case to be obvious and as a result, the rejection is maintained.
Conclusion
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.
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/A.J.B./Examiner, Art Unit 1765
/JOHN M COONEY/Primary Examiner, Art Unit 1765
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