DETAILED ACTION
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Any new grounds of rejection set forth below are necessitated by Applicant’s amendment.
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 1-20 are pending.
Claim Rejections - 35 USC § 103
Claims 1-2, 11-14 are rejected under 35 U.S.C. 103 as being unpatentable over Taplan et al. (JACS 2021 143 (24), 9140-9150) in view of Tournilhac et al. (US 2015/0125646) and Long et al. (US 2022/0315719).
Regarding claim 1: Taplan is directed to a recyclable vitrimer polymer composition (abstract) comprising:
A first monomer containing at least one amine group at the terminal thereof; and
A second monomer containing at least one acrylate group at the terminal thereof, and
No catalyst,
Wherein the recyclable vitrimer polymer composition is made by a method comprising:
Mixing and heating the first monomer and second monomer, wherein the N-H group of the first monomer and the acrylate group of the second monomer react with each other in a ratio of 1:0.5 to 1.5. Specifically, the reaction below illustrates the first and second monomers are mixed and heated in a molar ratio of 1:1.3. Further, the composition is highly crosslinked although can be reprocessed up to 10 times (equivalent to a vitrimer in light of the present specification).
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A heat dissipating filler is not mentioned.
Tournilhac is directed to a composite comprising a thermally conductive polymer material having a network that is characterized by reorganize by exchange reactions (abstract Tournilhac) and is recyclable ([0354] Tournilhac). The composite comprises a heat dissipating filler, e.g. Graphene, boron nitride ([0077] Tournilhac). One skilled in the art would have been motivated to have included the heat dissipating filler of Tournilhac to produce a composite thermal interface having thermal conductivity. Therefore, it would have been obvious to one skilled in the art at the time the invention was filed to have included a heat dissipating filler in Taplan to arrive at claim 15. With regards to the domains of the vitrimer polymer, one skilled in the art would expect the filler in Taplan to be separated from domains of the vitrimer polymer and positioned by between the domains since the same vitrimer polymer is disclosed.
A method comprising grinding the vitrimer polymer into a powder, mixing with the heat dissipating filler, and thermally molding the powder coated with the filler to form a composite is not mentioned.
Long is directed to a method for fabricating or repairing a fiber reinforced composite comprising a powder vitrimer polymer composition. The method comprises combining a powder and filler of reinforcing fiber, fusing the powder with the filler, and shaping the resulting composition into a composite (Fig. 3 Long). The method comprises grinding to form the powder ([0051] Long). Utilizing the method of Long in Taplan and Tournilhac results in coating the ground vitrimer powder with the heat dissipating filler. One skilled in the art would have been motivated to have been motivated to have utilized the method of Long since storing as a powder since grinding into a powder allows for large volumes and stockpiled for future use ([0051] Long) and thermally molding the vitrimer powder coated filler forms a composite. Therefore, it would have been obvious to one skilled in the art at the time the invention was filed to have utilized the method of Long to arrive at claim 1 of the present invention.
Regarding claim 2: Jeffamine D2000 is disclosed (Figure 2) (equivalent to formula 1 wherein n is 1 to 5 as defined by the present specification).
Regarding claim 12: The esters promote catalyst free transesterification with the advantage of maintaining crosslinking points (p. 9141 1st col.) (equivalent to a vitrimer polymer network topology rearranged through a transesterification reaction).
Regarding claim 13: The vitrimer polymer is capable of being recycled without a catalyst (p. 9146 Reprocessability).
Regarding claim 14: The polymer is capable of being recycled using a non-toxic solvent. Specifically, THF was used in the working examples (a non-toxic solvent as defined by the present invention).
Regarding claim 15: One skilled in the art would expect the filler in Taplan to be separated from domains of the vitrimer polymer and positioned by between the domains since the same vitrimer polymer and same heat dissipating filler is utilized.
Regarding claim 16: Thermally conductive fillers include graphene or boron nitride ([0077] Tournilhac).
Regarding claim 17: The thermal conductivity of the composite is preferably 0.5 W/mK or higher, and therefore at least overlaps the claimed range.
A prima facie case of obviousness typically exists when the ranges of a claimed composition overlap the ranges disclosed in the prior art. In re Peterson, 315 F.3d 1325, 1329 (Fed. Cir. 2003).
Regarding claim 18: Both Taplan and Tournilhac disclose the composition and composite are recyclable.
Claims 3-4 are rejected under 35 U.S.C. 103 as being unpatentable over Taplan, Tournilhac , and Long as applied to claim 1 above, and further in view of Grauzeliene et al. (ACS Applied Polymer Materials 2023 5 (9), 6958-6965).
Regarding claim 3: Taplan doesn’t mention formula 2.
Grauzeliene is directed to a vitrimer comprising a glycerol 1,3-diglycerolate diacrylate monomer (equivalent to formula 2). One skilled in the art would have been motivated to have selected the monomer of Grauzeliene as the acrylate monomer of choice in Taplan since it is a byproduct of biodiesel production from vegetable oil and animal fats, apart from having hydroxyl and ester groups required for transesterification (6959 1st col. Grauzeliene). Therefore, it would have been obvious to one skilled in the art at the time of the invention to have selected the glycerol 1,3-diglycerolate diacrylate monomer of Grauzeliene as the diacrylate monomer of choice in Taplan to arrive at claim 3 of the present invention.
Regarding claim 4: Selection of the glycerol 1,3-diglycerolate diacrylate monomer and poly(propylene glycol) bis(2-aminopropyl ether) is the same as the reaction scheme 1 of the present invention, and therefore there is a reasonable basis to conclude the vitrimer polymer would be represented by present formula 3.
Case law holds that the claimed and prior art products are identical or substantially identical in structure or composition, or are produced by identical or substantially identical processes, a prima facie case of either anticipation or obviousness has been established. In re Best, 562 F.2d 1252, 1255, 195 USPQ 430, 433 (CCPA 1977). MPEP 2112.01(I).
Hence, Taplan in view of Grauzeliene suggests a vitrimer represented by formula 3. Since PTO cannot conduct experiments the proof of burden is shifted to the applicants to establish an unobviousness difference, see In re Best, 562 F.2d 1252, 195 USPQ 430 (CCPA 1977). See MPEP § 2112.01.
Response to Arguments
Applicant's arguments filed 6/16/2026 (herein “Remarks”) have been fully considered but they are not persuasive.
Applicant argues (p. 10-12 Remarks) the amended claim 1 now requires a heat dissipating filler, no catalyst, mixed, and formed into a composite. None of the references cited disclose or suggest the presently claimed vitrimer polymer may be used for a purpose that would include a heat dissipating filler. Hence, a skilled person would not have had a reason to add a heat dissipating filler to Taplan. Further, Tournilhac’s discloses the necessary presence of at least one transesterification catalyst.
This argument is not found persuasive since one skilled in the art would have been motivated to have included the heat dissipating filler of Tournilhac to produce a composite thermal interface having thermal conductivity. With regards to the catalyst in Tournilhac, one cannot show nonobviousness by attacking references individually where the rejections are based on combinations of references. See In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981); In re Merck & Co., 800 F.2d 1091, 231 USPQ 375 (Fed. Cir. 1986). In the present case, Tournilhac’s catalyst has nothing to do with selecting a filler from Tournilhac for use in Taplan.
Applicant argues unexpected results of excellent recyclability as illustrated in the Examples.
The burden of showing unexpected results rests on the person who asserts them by establishing that the difference between the claimed invention and the closest prior art was an unexpected difference. See In re Klosak, 455 F.2d 1077, 1080 (CCPA 1972). Further, the showing of unexpected results must be commensurate in scope with the claims. See In re Peterson, 315 F.3d 1325, 1330-31 (Fed. Cir. 2003). In the present case, the working examples utilize specific first and second monomers. In contrast, the present claims include any first amine terminated and second acrylate terminate monomer in any amount (beyond the about equimolar amounts). For this reason alone, the claims are not considered commensurate in scope with the evidence provided.
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.
Contact Information
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ROBERT T BUTCHER whose telephone number is (571)270-3514. The examiner can normally be reached Telework M-F 9-5 Pacific Time Zone.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Lanee Reuther can be reached at (571) 270-7026. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/ROBERT T BUTCHER/Primary Examiner, Art Unit 1764
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