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 .
Claims 24, 26-30, 32, 34-44, 47, 49 and 50 are pending as amended on 2/16/2026.
The rejections have been modified solely to reflect the amendments to claim 24. Therefore, this action is properly made final. Any rejections and/or objections made in the previous Office action and not repeated below are hereby withdrawn. The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office Action.
Claim Rejections - 35 USC § 112
Claims 24, 26-30, 32, 34-44, 47, 49 and 50 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Claim 24 has been amended to recite a concentration of lactone monomer “based on the total volume of the solvent or the solvent and the second solvent.” The second solvent is an optional solvent. For a method as encompassed by claim 24 wherein the guanidine derivative is added in a second solvent, it is not clear whether the “total volume” must include the volume of “the second solvent,” or, whether the “total volume” could be just the volume of “the solvent.” Given that the second interpretation does not find support in the specification as filed, for examination purposes, the claim has been interpreted as requiring a particular concentration of lactone monomer based on the total volume of the solvent and the optional second solvent (such that if the optional second solvent is used, the volume of second solvent must be included in the “total volume” when calculating monomer concentration). Claims 26-30, 32, 34-44, 47, 49 and 50 are rejected for the same reason because they depend from claim 24.
Claims 28-30 depend from claim 27, which depends from claim 26. Claims 26 and 27 recite “a first lactone or derivative thereof” and a second lactone or derivative thereof.” Claim 28 further limits “the first lactone” recited in claim 27, and claim 29 further limits “the second lactone” recited in claim 27. Claim 30 further limits “the first lactone” and “the second lactone.” The language “or derivative thereof” is not inserted after “lactone” in claims 28-30. Therefore, it is not clear whether a method according to claims 28-30 limits embodiment wherein the lactone is “a derivative thereof.” Because “the first lactone” and “the second lactone” does not have clear antecedent basis, the scope of claims 28-30 is unclear.
Claim Rejections - 35 USC § 103
Claim(s) 24, 26-30, 32, 34-39, 41-44, 47, 49 and 50 is/are rejected under 35 U.S.C. 103 as being unpatentable over Fiore et al (High Tg aliphatic polyesters by the polymerization of spirolactide derivatives, Polym. Chem., 2010, 1, 870–877).
As to claims 24, 26-30, 36, 38, 39, 41, 42, 44, 47 and 50, Fiore discloses a method of copolymerization comprising admixing lactide (“L”) (corresponding to a first lactone monomer as recited in claims 26, 28 and 30, and the presently elected first lactone species) and norbornene-lactide (“NL”) (corresponding to a second lactone monomer as recited in claims 27, 29, 30, 34 and 35, and the presently elected second lactone species) in the presence of TBD as catalyst (corresponding to a guanidine derivative as recited in claim 24, and having a structure as recited in claims 38 and according to the first structure shown in claim 39). See Scheme 2 on p 874 of Fiore.
Fiore discloses a polymerization procedure wherein the lactone monomers (L and NL) are combined with aprotic organic solvent (CH2Cl2), and admixed with TBD (0.25 mol% TBD based on the total mols of monomers, which falls within the presently claimed range of 0.01 to 5 mol%; see Table 1, footnote “a”) in the same type of solvent (CH2Cl2) with initiator (benzyl alcohol, which is recited in instant claim 42). A polymer product (corresponding to the presently recited lactone polymer) is formed. See p 871, lower left. Fiore exemplifies a copolymer of L and NL which has a PDI of 1.58 (within the claimed range of 1.8 or less) and a molecular weight of 41 kDa, which falls within the range of 35kDa or more (as well as within the range recited in claim 44). See p 872, top left; Mn = 26 kg/mol and PDI = 1.58; PDI = Mw/Mn, and therefore, Mw = 41 kg/mol (26*1.58).
As to the recited temperature of the cooled mixture of lactone monomers and solvent of about -30 C to about -110 C.
Fiore teaches a representative procedure where the mixing (reacting) of monomers and solvent with TBD is carried out at -20 C (p 871, bottom right; p 872, top left). Fiore teaches that the polymerization of lactide proceeds by the release of ring-strain upon opening of the lactide ring, and a bulky side group can limit the exothermicity of this process. Polymerization of lactide derivatives at low temperatures shifts the equilibrium towards polymer formation (p 875, left). The reaction temperature exemplified by Fiore (-20 C) falls just outside the claimed range (while the presently recited upper endpoint of “about -30 C” encompasses some values above -30 C in view of the term “about,” the range is not considered to encompass -20 C). However, Fiore’s teaching regarding the effect of reaction temperature on equilibrium shift would have motivated one having ordinary skill in the art to optimize reaction temperature in order to achieve a desired molecular weight and/or yield/conversion. Additionally, as set forth in MPEP 2144.05 II A, differences in temperature will not support the patentability of subject matter encompassed by the prior art unless there is evidence indicating such temperature is critical. It would have been obvious to the person having ordinary skill in the art, therefore, to have admixed lactone monomers (L and NL) and guanidine derivative (TBD) in solvent (CH2Cl2) at a low temperature, as disclosed by Fiore, by selecting any appropriately low temperature, including a temperature within the presently claimed range of about -30 C to about -110 C (as in claim 24), or about -70 C to about -90 C (as in claim 36), thereby arriving at a process of admixing a cooled mixture of lactone monomers and solvent (a) and guanidine derivative (b).
As to the recitation that the concentration of lactone monomers ranges from about 0.01 to about 10 w/v%, based on the total volume of solvent upon admixing:
Fiore exemplifies a polymerization (see p 871, lower right) wherein upon admixing, there are 0.206 grams lactone monomers (0.031+0.175) in 1.06 mL of solvent (0.890+0.170), which corresponds to a lactone monomers concentration of 19 w/v% (0.206/1.06*100) based on total volume of solvent. Therefore, Fiore’s exemplified concentration of lactone monomers falls outside the claimed range of 0.01 to 10 w/v%. However, reactant concentration is a variable which is routinely optimized by a synthetic chemist in order to affect reaction results including byproduct formation, reaction rate and/or viscosity of a reaction solution. Additionally, as set forth in MPEP 2144.05 II A, differences in concentration will not support the patentability of subject matter encompassed by the prior art unless there is evidence indicating such concentration is critical. It would have been obvious to the person having ordinary skill in the art, therefore, to have admixed lactone monomers (L and NL) and guanidine derivative (TBD) in solvent (CH2Cl2) at a low temperature, as disclosed by Fiore, by selecting any appropriate concentration of lactone monomers in reaction solvent, including a concentration within the presently claimed range of about 0.01 to 10 w/v% (claim 24), or about 5 w/v% to about 10 w/v% (claim 41).
As to claim 32, Fiore exemplifies copolymers having mole ratios of NL (based on NL and L monomer feed) ranging from 0.9 to 0.2 (see Table 1 on p 874), which corresponds to a ratio of L:NL of 1:9 to 8:2. Several of the mole ratios in Fiore’s Table 1 fall within the presently claimed range (when the instant first lactone is L and the instant second lactone is NL, such as in the elected species), including, e.g., XNL of 0.5 (which corresponds to a 1:1 ratio).
As to claims 34 and 35, Fiore fails to teach a method wherein there is a second addition of monomers after admixing the cooled mixture of monomers and guanidine catalyst. However, the selection of any order of mixing ingredients is prima facie obvious. See MPEP 2144.04(IV)(C). Therefore, in the absence of any showing of criticality associated with the order in which monomers and catalyst are admixed, it would have been obvious to the person having ordinary skill in the art to have modified the process disclosed by Fiore by mixing ingredients (i.e., the lactide and norbornene-lactide monomers, catalyst/initiator, solvent) in any sequence in order to provide Fiore’s desired polymerizable reaction mixture comprising monomers and catalyst, including mixing together a first amount of the L and NL monomers and catalyst, and then adding a remaining amount of the L and NL monomers (corresponding to the presently recited second mixture of monomers which comprises the first and second lactone) thereto.
As to claim 37, Fiore exemplifies a process (see p 871, lower right) wherein lactone monomers and solvent are mixed with catalyst (TBD), initiator (benzyl alcohol) and solvent, and the reaction vial is placed in a freezer for the duration of the reaction. Fiore fails to disclose the temperature of the mixture of lactone and solvent prior to combining/admixing with the mixture of catalyst/initiator and solvent. However, given Fiore’s disclosure that the equilibrium of the polymerization reaction is shifted toward polymer formation at lower temperatures (p 875, left), the person having ordinary skill in the art would have been motivated to cool Fiore’s monomer/solvent mixture to a desired reaction temperature prior to combining with Fiore’s catalyst/initiator in order to eliminate any reaction which would otherwise initially occur at an undesired higher temperature (i.e., while the reaction mixture cools to the set/desired reaction temperature). It would have been obvious to the person having ordinary skill in the art, therefore, to have cooled Fiore’s mixture of monomers (L and NL) and solvent prior to initiating reaction by combining with catalyst and initiator for any appropriate length of time needed to reach the desired temperature for reaction (e.g., depending on the quantity of material needing to be cooled), including for about 30 minutes as presently recited.
As to claim 43, Fiore exemplifies polymerizations utilizing various mole ratios of NL to L. Fiore teaches that the reaction times varied depending on the mole ratios of monomers in the feed, with higher mole ratios of NL requiring longer reaction times (p 874, left). As shown in Table 1, Fiore varies the amount of time for the reaction from 5 to 14 days for copolymers, and achieves yields ranging from 29-78% and number average molecular weights ranging from 16-28 kg/mol. Considering Fiore’s disclosure, the person having ordinary skill in the art would have been motivated to optimize a reaction time for any given mole ratio of NL at any appropriate reaction temperature (by determining how the molecular weight and yield of the obtained polymer changes as the reaction length changes) in order to achieve a balance between desired polymer properties (e.g., molecular weight and yield) and process efficiency. It would have been obvious to the person having ordinary skill in the art, therefore, to have reacted (“admixed”) NL and L, as suggested by modified Fiore, for any appropriate duration which achieves a desired polymer molecular weight and yield for a selected NL:L molar ratio, including a duration within the presently claimed range of about 1 to 24 hours.
As to claim 49, Fiore teaches polymerizations of the same monomers (NL and L) in the same solvent (CH2Cl2, i.e., DCM) as utilized in the instant “General Procedure of the Ring-Opening Polymerization” (Example 2). According to the instant example, the resulting copolymer is soluble in the solvent at the cooled temperature. Given that Fiore suggests a process using the same catalyst (TBD) to form a polymer from the same monomers (NL and L) in the same solvent as in instant example 2, there is reasonable basis to conclude that the copolymer produced in Fiore’s process has substantially the same solubility in cooled CH2Cl2 as in instant Example 2 (i.e., Fiore’s obtained polymer is substantially soluble in cooled CH2Cl2 as presently recited).
Claim(s) 40 is/are rejected under 35 U.S.C. 103 as being unpatentable over Fiore et al (High Tg aliphatic polyesters by the polymerization of spirolactide derivatives, Polym. Chem., 2010, 1, 870–877) in view of Jing et al (US 2009/0306333).
The rejection of claim 24 over Fiore is incorporated here by reference.
As discussed, Fiore discloses a polymerization procedure wherein the lactone monomers (L and NL) are combined with aprotic organic solvent (CH2Cl2), and admixed with TBD, wherein TBD is present in an amount of 0.25 mol% based on the total mols of monomers (see Table 1, footnote “a”). The amount of TBD catalyst exemplified by Fiore falls outside the presently claimed range of about 0.05 to about 0.2 mol%.
Jing discloses the same norbornene lactide (NL) monomer taught by Fiore [0008], and discloses a lactide opened homopolymer formed by reacting NL monomer with catalyst and initiator, wherein the catalyst taught by Jing is the same catalyst taught by Fiore (TBD) and the initiator taught by Jing is the same initiator taught by Fiore (benzyl alcohol). See Jing [0011]. Jing teaches that the molecular weights of the polymer could be controlled by increasing the amount of NL monomer relative to the catalyst and initiator amounts, and that using less relative amounts of catalyst and initiator could achieve an increase in the molecular weight of the resulting polymer [0052].
As an example, Jing teaches a polymerization resulting in increased molecular weight wherein the guanidine derivative TBD catalyst is present in an amount of 0.16 mol%, which falls within the presently claimed range [0052]. (0.20 g of NL is 0.96 mmol, see [0046]; 0.22 mg of TBD = 1.58 umol of TBD, calculated based on teaching in [0046] that 6.7 mg of TBD is 48 umol; the mol% of TBD in the reaction in [0052] is therefore 0.00158 mmol TBD/0.96 mmol NL = 0.16%.) Considering Jing’s disclosure, when carrying out a polymerization of lactone monomers including NL in the presence of TBD catalyst and benzyl alcohol initiator, as taught by Fiore, it would have been obvious to the person having ordinary skill in the art to have decreased the amount of TBD catalyst relative to lactone monomers, such as to 0.16 mol% as taught by Jing, in order to increase the molecular weight of the resulting polymer.
Response to Arguments
Applicant's arguments filed 2/16/2026 have been fully considered.
Applicant argues (p 14) that the instant specification describes ([0065-67]) achieving unexpectedly high molecular weights and low polydispersity indices at a low temperature and low concentration of monomer. However, Applicant’s argument is not sufficient to overcome the prima facie case of obviousness over Fiore for at least the reason that Applicant has not provided any evidence or data directly comparing the reaction conditions (temperature/monomer concentrations) taught in the prior art to reaction conditions which are encompassed by the instant claims and which are alleged to be associated with unexpected results. Without such data/evidence, it is not possible to determine whether the claimed method achieves unexpected results. See MPEP 716.02(e) (Applicant must compare the claimed subject matter with the closest prior art to be effective to rebut a prima facie case of obviousness).
Furthermore, without comparative data/evidence, it is not possible to determine whether such results are commensurate in scope with the claimed subject matter. The instant specification describes only one example comprising steps according to the claimed method (example 2) and contains no comparative example. The instant example utilizes very specific monomers (lactide, norbornene-lactide) in a specific ratio and concentration (5%), a specific solvent (CH2Cl2), a specific catalyst (TBD) in a specific amount (0.5 mol%) with no initiator, at a specific temperature (-80 C) for a specific duration (24 hr). [It is not clear whether the exemplified method is encompassed by the instant claims because the molecular weight and PDI of the resulting polymer are not reported.] In contrast, the method recited in instant claim 24 is very broad in terms of the lactone monomer (not limited to any particular structure, i.e., not limited to lactide or norbornene-lactide), the type of guanidine catalyst (not limited to TBD), the solvent, the catalyst amount, the monomer concentration (encompasses values as low as 0.01 w/v%), the reaction temperature (encompasses -30 C) and the presence of initiator. Evidence of nonobviousness must be commensurate in scope with the claims which the evidence is offered to support. See MPEP 716.02(d). Therefore, if Applicant wishes to overcome the present rejection by showing unexpected results, Applicant must provide sufficient evidence to show that unexpected results would be obtained for all species encompassed by the present claims.
Regarding the rejection of claim 40 over Fiore in view of Jing:
Applicant argues that Jing does not teach/suggest lowering the temperature to arrive at the claimed molecular weight/PDI. However, Jing was not relied on for such a teaching. Rather, Jing was relied on to establish the obviousness of changing the amount of TBD catalyst taught by Fiore. Therefore, Applicant’s argument does not overcome the rejection over Fiore in view of Jing because it does not address the manner in which Jing was relied on to modify Fiore.
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.
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/RACHEL KAHN/Primary Examiner, Art Unit 1766