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 .
DETAILED ACTION
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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 6/22/26 has been entered.
Response to Amendment
The amendment is supported by the original disclosure.
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
The previous restriction, ODP, and 103 rejections have been maintained, but the position has been modified due to the amendment.
Claim Rejections - Double Patenting
Claim(s) 14 is (are) rejected on the ground of nonstatutory obviousness-type double patenting as being unpatentable over claims 11-12 of copending Application No. 18017900. This is a provisional obviousness-type double patenting rejection because the conflicting claims have not in fact been patented.
‘900 (claims 11-12) meets instant claims 14, because it discloses:
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The decarboxylated end groups content meets the claimed range. The resultant Mw would be expected ≥30k (due to the polydispersity), overlapping with the claimed range. It has been found that where claimed ranges overlap ranges disclosed by the prior art, a prima facie case of obviousness exists - see MPEP 2144.05.
Claim Rejections - 35 USC § 103
Claim(s) 14 is (are) rejected under 35 U.S.C. 103(a) as being unpatentable over Shirahama et al. (US 20180186927, listed on IDS and ISR) in view of Sato et al. (US 20230167232, eff. F/D:07/01/20).
As to claim 14, Shirahama (abs., claims, examples) discloses a mold (89, 100, Table 1) comprising a polyfurandicarboxylate (Ex.A2/A9,Table 2, [0282]) produced via polymerizing dimethyl 2,5-furandicarboxylate with 1,4-cyclohexanedimethanol) (meets the claimed diol of withdrawn claim 2) from biomass derived materials (2). Shirahama discloses Furandicarboxylate and furandicarboxylic acid can be equivalently used for polymerization (38). The polyfurandicarboxylate shows a Mw of 78.9k, measured by GPC (252-258) via hexafluoroisopropanol/ (5 mM of sodium trifluoroacetate) as the eluents and PMMA as the standard. The polyfurandicarboxylate can be further polymerized via solid state polymerization (Ex.A9).
It is duly notified 1,4-cyclohexanedimethanol can be construed as a cyclic alkylene diol, as obviously recognized by one of ordinary skill in the art. The original disclosure does not exclude cyclic alkylene diols from alkylene diols.
Shirahama is silent on using 0.05M of potassium trifluoroacetate. However, Shirahama further discloses a range of Mn (35k-80k,106), falling within the range of Mn (≥30k) of the claimed polyfurandicarboxylates according to instant [0069] (pgpub). The furandicarboxylate produced via condensational polymerization would be expected to have a PDI ≥1, as obviously recognized by one of ordinary skill in the art. In light of this, one of ordinary skill in the art would obviously recognize that Shirahama’s polyfurandicarboxylate (EX.A2) would be expected to exhibit a Mw falling withing or overlapping with the claimed range (≥40k) as measured by GPC using 0.05M of potassium trifluoroacetate. It has been found that where claimed ranges overlap ranges disclosed by the prior art, a prima facie case of obviousness exists - see MPEP 2144.05.
Shirahama is silent on the claimed amount of decarboxylated end groups in the polyester is less than 7 eq/t as determined by 1H-NMR using TCE-d2.
In the same area of endeavor of producing a mold (45, 52) comprising polyfurandicarboxylate derived from biomass (2), Sato (abs., claims, examples) discloses a method of producing polyfurandicarboxylate via furandicarboxylate or furandicarboxylic acid polymerized with 1,4-cyclohexanedimethanol (63-65). Sato discloses (29, 109-115, claim 6) a method of controlling the content of decarboxylated end groups ≤10 eq/t (measured via the claimed 1H-NMR method) overlapping with the claimed range. It has been found that where claimed ranges overlap ranges disclosed by the prior art, a prima facie case of obviousness exists - see MPEP 2144.05. Sato (110) teaches by controlling the decarboxylated end group content, a polycondensation reaction followed by solid phase polymerization is likely to result in further increased viscosity. Sato (110) teaches the decarboxylated end group content in the polyfurandicarboxylate can be adjusted by devising the conditions of esterification or transesterification and polycondensation reactions as described in the polycondensation steps (92-96). To reduce the decarboxylated end group content, esterification or transesterification is preferably performed such that the reaction rate is higher. Specifically, the reaction time at lower temperature is preferably longer. Thus, the reaction rate of esterification can be increased, and by-products can be less likely to occur. The polycondensation reaction is preferably performed from a lower temperature at the start of the reduced pressure because of less tendency to produce by-products. Accordingly, by determining the decarboxylated end group content of the polyfurandicarboxylate manufactured by performing the esterification or transesterification and polycondensation reactions under the preferred conditions in the polycondensation steps (92-96), and selecting a polyfurandicarboxylate raw material having a desired content, a polyfurandicarboxylate raw material in which the decarboxylated end group content is a specific amount or less can be obtained.
As to the new limitation, Sato (65) further discloses 1,4-cyclohexanedimethanol and 1,4-butanediol are functionally equivalent diols for producing polyfurandicarboxylate derived from biomass. Therefore, it would have been obvious to one of ordinary skill in the art to have replaced 1,4-cyclohexanedimethanol of Shirahama with 1,4-butanediol because of their equivalent functionality as diols for producing polyfurandicarboxylate for mold derived from biomass. These conditions appear to equally apply to both productions using similar phenoplast raw materials. This adaptation would have obviously yielded instantly claimed poly(butylene 2, 5-furandicarboxylate).
Therefore, as to claim 14, it would have been obvious to one of ordinary skill in the art to have modified the process disclosed by Shirahama (EX.A2/A9) and applied the method of polycondensation to control amount of decarboxylated end groups in view of Sato, because the resultant process would yield reduced by-products and increased viscosity in the sequential solid-state polymerization.
Allowable Subject Matter
The following is an examiner's statement of reasons for allowance:
Claim(s) 15 is(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.
Claim(s) 15 is(are) allowable over the closest prior art: Shirahama et al. (US 20180186927, listed on IDS and ISR) in view of Sato et al. (US 20230167232, eff. F/D:07/01/20).
The examiner agrees with applicant’s results and argument in 1.132. It is duly notified applicant’s merely show results of poly(ethylene 2, 5-furandicarboxylate) to defeat the rationale applied for the previous rejection.
Therefore, claims 15 is(are) allowable.
The examiner urges amendment of withdrawn claims for preparing claim rejoinder.
Any comments considered necessary by applicant must be submitted no later than the payment of the issue fee and, to avoid processing delays, should preferably accompany the issue fee. Such submissions should be clearly labeled “Comments on Statement of Reasons for Allowance”.
Response to Arguments
The argument for allowance of amended claims has been fully considered but not fully persuasive.
Applicant’s argument regarding the new limitation has been rendered moot. See above new ground rejection. The examiner agrees with applicant’s results and argument in 1.132. It is duly notified applicant’s merely show results of poly(ethylene 2, 5-furandicarboxylate) to defeat the rationale applied for the previous rejection.
Therefore, as to claim 14, it would have been obvious to one of ordinary skill in the art to have modified the process disclosed by Shirahama (EX.A2/A9) and applied the method of polycondensation to control amount of decarboxylated end groups in view of Sato, because the resultant process would yield reduced by-products and increased viscosity in the sequential solid-state polymerization. As to the new limitation, Sato (65) further discloses 1,4-cyclohexanedimethanol and 1,4-butanediol are functionally equivalent diols for producing polyfurandicarboxylate derived from biomass. Therefore, it would have been obvious to one of ordinary skill in the art to have replaced 1,4-cyclohexanedimethanol of Shirahama with 1,4-butanediol because of their equivalent functionality as diols for producing polyfurandicarboxylate for mold derived from biomass. These conditions appear to equally apply to both productions using similar phenoplast raw materials. This adaptation would have obviously yielded instantly claimed poly(butylene 2, 5-furandicarboxylate).
Therefore, the previous restriction, ODP, and 103 rejections have been maintained, but the position has been modified due to the amendment.
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 extension fee 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 date of this final action.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to SHANE FANG whose telephone number is (571)270-7378. The examiner can normally be reached on Mon-Thurs. 8am-6pm.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Randy Gulakowski can be reached on 571.572.1302. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/SHANE FANG/Primary Examiner, Art Unit 1766
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