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 .
Claim Status
Claims 1-8 were filed on 9/11/2023. In a preliminary amendment filed on the same day, claims 1, 3, 7, and 8 were amended and claims 5-6 were canceled. Claims 1-4, 7, and 8 are pending.
Priority
The Application was filed on 9/11/2023 and claims the benefit of priority to:
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See filing receipt dated 2/28/2024. Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Claim Objections
Claim 4 is objected to because of the following informalities: in claim 4, the label “[Chemical Formula 1]” should be deleted. The compound is referred to as “Formula (1)” in the preamble in the claim and also labeled as such in the body of the claim.
Appropriate correction is required.
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
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.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claims 1-4, 7, and 8 is/are rejected under 35 U.S.C. 103 as being unpatentable over Yamadoi (JP2019099540A, published on 6/24/2019, of record in the IDS filed on 9/11/2023, including English translation) as evidenced by 112-98-1 (SciFinder entry of tetraethylene glycol dibutyl ether, obtained on 4/9/2026) and 19327-38-9 (SciFinder entry of octyl triethylene glycol, obtained on 4/9/2026), 26009-03-0 (SciFinder entry of polyglycolic acid, obtained on 4/9/2026).
Applicant claims a method for producing glycolide, the method comprising: a first step of preparing a depolymerization reaction solution containing a glycolic acid oligomer, and a titanium alkoxide catalyst; and
a second step of producing glycolide by depolymerization of the glycolic acid oligomer,
a content of titanium element derived from the titanium alkoxide catalyst in the depolymerization reaction solution being 1.2 mmol/L or less.
Yamadoi teaches a process for producing glycolide which comprises subjecting polyglycolic acid (PGA, a glycolic acid oligomer, see lines 111-131 of the translation) to depolymerization to obtain glycolide using a depolymerization reaction liquid containing polyglycolic acid and a phosphine (a) or phosphine oxide (b):
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(see lines 131-160 of the translation). See abstract. Yamadoi further teaches that the reaction mixture contains a metal catalyst, including titanium alkoxides tetraisopropyl orthotitanate Ti(i-PrO)4 and normal (n) butyl orthotitanate Ti (n-BuO)4. Yamadoi teaches that the catalyst can be used in a concentration of 0.001 to 1000 mmol. See claims 4-5 and lines 246-259 of the translation. Yamadoi teaches that the reaction mixture further contains a solvent, preferably a high boiling point polar organic solvent (claim 3). See lines 162-239 of the translation. Yamadoi teaches that the solvent can be a polyalkylene glycol diether of instant formula (1) of claim 4, wherein instant R (R4 of Yamadoi) is methylene or a linear or branched alkylene group having 2 to 8 carbon atoms; and instant X, Y, and p are the same as those of Yamadoi. See claim 6 and lines 169-203 of the translation and [0045] of the original patent.
Yamadoi teaches reacting 126 g of polyglycolic acid (PGA, glycolic acid oligomer), 130 g of tetraethylene glycol dibutyl ether, 100 g of octyl triethylene glycol, 186 mg of triphenylphosphine (TPP) to produce glycolide. See examples 1 and 3 in lines 308-329). Yamadoi teaches examples 7 and 8, carried out according to the same conditions as example 3, which further comprise 40.2 g (0.71 mmol) of Ti(i-PrO)4 or 40.24 g (0.71 mmol) of Ti (n-BuO)4, see lines 343-349 of the translation and [0070-0071] and Table 1 in [0081] of the original patent.
Ti(i-PrO)4 and Ti (n-BuO)4 correspond to titanium tetraisopropoxide and titanium tetrabutoxide, respectively. Both are titanium alkoxides and present in 0.71 mmol.
Tetraethylene glycol dibutyl ether (TGDE) and octyl triethylene glycol (OTG) correspond to organic solvents (claim 3) and TBDE is a polyalkylene glycol diether solvent of instant formula (1) in claim 4, wherein X and Y are n-butyl, a C4 alkyl group, R is ethylene (-CH2-CH2-), and p is 4.
The reactions comprise 126 g PGA, 130 g TGDE, and 100 g OTG but Yamadoi does not give the volume of the PGA or solvents in liters (L). Therefore, these volumes were calculated using the predicted densities of both compounds, as evidenced by 112-98-1; 19327-38-7; and 26009-03-0:
130 g TGDE x [1 mL / 0.944 g] x [1 L / 1000 mL] = 0.14 L TGDE
100 g OTG x [1 mL / 0.95 g] x [1 L / 1000 mL] = 0.11 L OTG
126 g PGA x [1 mL / 1.5 g] x [1 L / 1000 mL] = 0.08 L PGA
Therefore, the total volume of the example is 0.14 + 0.11 + 0.08 = 0.33 L. TPP is also present, however only in mg amounts. Therefore, its contribution to the volume of the example mixture is negligible.
The concentration of the titanium element in examples 7 and 8 in the reaction solution is 0.71 mmol/0.33 L, or 2.2 mmol/L. This falls outside of the claimed range of 1.2 mmol/L. Therefore, Yamadoi does not explicitly teach that the content of the titanium element derived from the titanium alkoxide catalyst in the depolymerization reaction solution being 1.2 mmol/L or less of claim 1 (and 0.008 mmol/L or greater-claim 2).
It would have been prima facie obvious to arrive at the instantly claimed process based on the teachings of Yamadoi with a reasonable expectation of success before the effective filing date of the claimed invention. A person of ordinary skill in the art would have been motivated to decrease the concentration of the titanium alkoxide catalyst in the reaction because Yamadoi explicitly teaches that the catalyst concentration in the depolymerization reaction solution can fall anywhere in the range of 0.001 to 1000 mmol, more preferably 0.01 to 100 mmol, and further preferably 0.1 to 100 mmol. The first range encompasses the claimed ranges and the second to ranges of Yamadoi overlap with those claimed. Further, the skilled artisan would be motivated to decrease the catalyst loading to produce a more efficient reaction. If the total concentration of the titanium catalyst were decreased, then so would the concentration of the titanium (in mmol) to the solvent (in L). Therefore, Yamadoi teaches ranges which encompass and overlap with those claimed and indicate that these concentrations of titanium catalyst will predictably facilitate the claimed reaction with a reasonable expectation of success. Also see MPEP 2144.05.
Further regarding claim 7, Yamadoi teaches that the polyglycolic acid is prepared in a preliminary step and then combined with the glycolic acid oligomer, solvent, and phosphine additive. See examples in lines 300-356 of the translation. Yamadoi does not explicitly teach that the catalyst is added to the glycolic acid oligomer, however, the selection of any order of performing process steps and/or mixing ingredients is prima facie obvious in the absence of new or unexpected results. See MPEP 2144.04(IV)(C). Further, the depolymerization reaction requires stirring at an elevated temperature (235°C) under a vacuum for an extended period of time. Therefore, it is unlikely that the order of addition of the catalyst and glycolic acid oligomer at room temperature provides criticality to the process.
Regarding claim 8, Yamadoi teaches that the glycolide is continuously distilled out of the reaction mixture and replaced with polyglycolic acid equivalent to 1.1 times the mass of the distilled (recovered) glycolide. See lines 313-321 of the translation.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to AMY C BONAPARTE whose telephone number is (571)272-7307. The examiner can normally be reached 11-7.
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/AMY C BONAPARTE/ Primary Examiner, Art Unit 1692
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