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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 10/21/2025 has been entered.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claim 18 is rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends. Claim 18 broadens the molar ratio of the monomers of claim 1. Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
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.
A1. Claims 1-5, 7-12, 19-20, 22-25 and 28 are rejected under 35 U.S.C. 103 as being unpatentable over Kainulainen et al. (UV-Blocking Synthetic Biopolymer from Biomass-Based Bifuran Diester and Ethylene Glycol; Macromolecules 2018, 51, 1822-1829, provided on IDS).
Regarding claims 1, 2, 4 and 5, Kainulainen teaches polyester derived from dimethyl 2,2′-bifuran-5,5′-dicarboxylate and ethylene glycol (scheme 2, page 1825) as depicted below, corresponding to the repeating units of (i) and (ii) as required by the claim.
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Kainulainen further highlights (last para, page 1828; Introduction, page 1822, third para: with furans as building blocks of polymers) that copolymers of the dimethyl 2,2′-bifuran-5,5′-dicarboxylate (monomer 3 in the scheme 2 provided above) could be useful for enhancing and modifying the mechanical, thermal or barrier characteristics of materials in a green manner. With the goal to provide new materials that simultaneously contain the desirable properties of the widely used polyester such as PET while also benefiting from the barrier property improvements offered by the bifuran carboxylate a skilled artisan would incorporate such a monomer to a petrochemical polyester (derived from terephthalic acid or its ester derivative to generate PET, as depicted in Scheme 1, page 1823), just as the reference documents with 4,4’-biphenyldicarboxylic acid (BDA) (pg 1822, right column). An obvious copolyester gleaned from the teachings of Kainulainen would be where dimethyl 2,2′-bifuran-5,5′-dicarboxylate, ethylene glycol and terephthalic acid (corresponding to the required aromatic C8 dicarboxylic monomer residue (iii)), are utilized to create a modified biomass derived PET with improved barrier properties.
The reference is silent on the possible ratio of the diacid monomers, however recognizes that each of the diacid (derivatives) contributes different properties to the obvious copolymer, e.g. the improved gas permeability demonstrated by polymers derived from the furan-based monomer relative to that from a terephthalic acid-based polymer (Conclusion, 2nd para, page 1827). When the ratio is outside of the lower limit of the disclosed ratio of units (i) to (iii), the amount of the former will be so small as to exert a negligible effect on the properties of the copolymer so it would be obvious that the obvious copolymer should conform to the limitation.
Regarding claims 3 and 7, as discussed when addressing claim 1, Kainulainen teaches terephthalic acid (Scheme 1, page 1823) and further highlights (second para, page 1825) that dimethyl based carboxylic acid diester polymerize more favorably, thus encouraging a skilled artisan to substitute dimethyl terephthalate (DMT) for terephthalic acid for the creation of the copolyester.
Regarding claims 8 and 11-12, as discussed when addressing claim 1, the obvious copolyester of Kainulainen derived from dimethyl 2,2′-bifuran-5,5′-dicarboxylate, terephthalic acid (or DMT), and ethylene glycol would generate the structure of Formula (III) with random repeat units where R3 is
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132
73
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and R4 is –(CH2)2-, where x and y would be expected to be at least 1 or more.
Regarding claims 19-20, Kainulainen teaches (second para, Introduction, page 1822) creation of beverage and food packaging derived from PET. Obvious copolyester of Kainulainen as discussed in claim 1 could similarly be utilized for a more green food packaging option.
Regarding claims 22-25 and 28, As discussed when addressing claim 1, an obvious copolyester of Kainulainen is derived from monomers dimethyl 2,2′-bifuran-5,5′-dicarboxylate, ethylene glycol and dimethyl terephthalate. Kainulainen teaches the first polymerization step in the presence of tetrabutyl titanate (Kainulainen page 1823, last para) conducted under Ar (scheme 2), at a temperature of 180 degrees C, consistent with step (B). The polymerization reaction is further carried to a temperature of 270 degrees C which is 10 degrees higher than the range of step (c) under vacuum. A skilled artisan would appreciate that these exact temperatures do not have to be used and any temperature that promotes full condensation and removal of by-product would suffice.
A2. Claims 1, 8-10, 22 and 26 are rejected under 35 U.S.C. 103 as being unpatentable over Kainulainen et al. (UV-Blocking Synthetic Biopolymer from Biomass-Based Bifuran Diester and Ethylene Glycol; Macromolecules 2018, 51, 1822-1829, provided on IDS).
Regarding claim 1, Kainulainen teaches polyester derived from dimethyl 2,2′-bifuran-5,5′-dicarboxylate and ethylene glycol (scheme 2, page 1825) as depicted below, corresponding to the repeating units of (i) and (ii) as required by the claim.
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Kainulainen further highlights (last para, page 1828; Introduction, page 1822, second and third para: with furans as building blocks of polymers) that copolymers of the dimethyl 2,2′-bifuran-5,5′-dicarboxylate (monomer 3 in the scheme 2 provided above) could be useful for enhancing and modifying the mechanical, thermal or barrier characteristics of materials in a green manner. Kainulainen notes that 2,5-furandicarboxylic acid (2,5-FDCA) has been the choice for building novel materials and used for the preparation of various polyesters, thus encouraging an artisan skilled in the art to copolymerize both furan-based monomers 2,5-FDCA and 2,2′-bifuran-5,5′-dicarboxylic acid (both monomers or ester derivatives are presented in Scheme 1, page 1823, Scheme 2 compound 3 and second para 1825: dimethyl 2,5-furandicarboxylate). Thus, obvious copolyester of Kainulainen would be where dimethyl 2,2′-bifuran-5,5′-dicarboxylate, ethylene glycol and dimethyl 2,5-furandicarboxylate (corresponding to the required aromatic C6 dicarboxylic monomer residue (iii)), are utilized to create a biomass derived polyester with improved barrier characteristics.
The reference is silent on the possible ratio of the diacid monomers, however recognizes that each of the diacid (derivatives) contributes different properties to the obvious copolymer, e.g. the improved gas permeability demonstrated by polymers derived from the furan-based monomer relative to that from a terephthalic acid-based polymer (Conclusion, 2nd para, page 1827; 3rd para, page 1828). When the ratio is outside of the lower limit of the disclosed ratio of units (i) to (iii), the amount of the former will be so small as to exert a negligible effect on the properties of the copolymer so it would be obvious that the obvious copolymer should conform to the limitation.
Regarding claims 8-10, as discussed in claim 1, the obvious copolyester of Kainulainen derived from dimethyl 2,2′-bifuran-5,5′-dicarboxylate, dimethyl 2,5-furandicarboxylate and ethylene glycol would generate the structure of Formula (III) with random repeat units and where R3 is
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90
195
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and R4 is –(CH2)2-, where x and y would be expected to be at least 1 or more.
Regarding claim 22, as discussed, when addressing claim 1, obvious copolyester of Kainulainen is derived from monomers dimethyl 2,2′-bifuran-5,5′-dicarboxylate, ethylene glycol and dimethyl 2,5-furandicarboxylate. Kainulainen teaches the first polymerization step in the presence of tetrabutyl titanate (Kainulainen page 1823, last para) conducted under Ar (scheme 2), at a temperature of 180 degrees C, consistent with step (B). The polymerization reaction is further carried to a temperature of 270 degrees C which is 10 degrees higher than the range of step (c) under vacuum. A skilled artisan would appreciate that these exact temperatures do not have to be used and any temperature that promotes full condensation and removal of by-product would suffice.
Regarding claim 26, Kainulainen teaches dimethyl 2,5-furandicarboxylate, and notes that the dimethyl ester derivative of 2,5-FDCA behaves more favorably under various polyesterification conditions as compared to the acid form, meeting the claimed requirement (page 1825, second para).
Allowable Subject Matter
Claims 13, 14, 16, 27, 29, 30, 34 and 35 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 prior art on record is silent on the thiophene based monomer residues as required by claim 13.
Reference Kainulainen only discloses the aliphatic diol ethylene glycol, thus the claimed limitation (claims 14 and 27) of butanediol is not rendered obvious.
The specific monomers, monomer ratios and the range of monomer ratios as required by claims 16, 29, 30, 34 and 35 are not made obvious by Kainulainen.
Response to Arguments
Applicant's arguments filed on 10/21/2025 have been fully considered but they are not persuasive.
Applicant has amended the independent claims 1 and 22 to include the features of allowable claim 35, with the exception that the lower end of the stated molar ratio of the monomers is expanded to 1:100 vs 10:90. Applicant notes that Kanulainen 2018 does not suggest the specific molar ratio range now claimed. While it is acknowledged that Kanulainen does not teach the required molar ratio range, as discussed in the rejection above, Kanulainen discusses the benefits of improved permeability derived from furan based monomers. For one of ordinary skill, it would be obvious to try minimal amount of the bifuran monomer in a mostly PET backbone, such as the molar ratio of 1:100 as a starting point to observe either incremental or substantial property benefits. Applicant’s attention is also brought to MPEP 2144.01 Implicit Disclosure “"[I]n considering the disclosure of a reference, it is proper to take into account not only specific teachings of the reference but also the inferences which one skilled in the art would reasonably be expected to draw therefrom." In re Preda, 401 F.2d 825, 826, 159 USPQ 342, 344 (CCPA 1968).
The unexpected results as provided by literature references Kainulainen et al., Biomacromolecules 2020, 21, 743-752 (“Kainulainen 2020”) and Ahmed et al. Ind. Eng. Chem. Res. 2021, 60, 7495-7504 (Ahmed), cannot be relied upon since they were published after the parent filing date of 371 PCT/FI2019/050487 of 06/20/2019.
It is additionally noted for the relevant data to be considered, it needs to be submitted under Affidavits or Declarations Under 37 CFR 1.132 and Other Evidence Traversing Rejections, please see MPEP 716.
The rejections as presented above in the office action over Kainulainen 2018 are thus maintained.
Conclusion
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/S.M.D./
Examiner
Art Unit 1765
/MARC S ZIMMER/Primary Patent Examiner, Art Unit 1765