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 .
Information Disclosure Statement
NPL Ref Cite #1 has been lined through in the IDS received 7/6/2023 because a legible copy of the cited NPL document has not been submitted. Rather, it appears only the supporting information for the associated journal article was provided. 37 CFR 1.98(a) requires a legible copy of each NPL document.
Claim Objections
Claims 3 and 18 are objected to because of the following informalities: claims 3 and 18 do not end with a period. Appropriate correction is required.
Claim 10 is objected to because of the following informalities: “Dibutyl terephthalate” is misspelled. Appropriate correction is required.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 1-20 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 1 recites “a step of depolymerizing the PET in an ester of terephthalate and monoethylene glycol (MEG)”, which literally suggests depolymerizing PET in a reaction mixture comprised of terephthalate ester and monoethylene glycol. However, the specification appears to be descriptive of terephthalate ester and monoethylene glycol as reaction products of the depolymerization process (see ¶ 14: “polyethylene terephthalate (PET) polymer into terephthalate and monoethylene glycol ester (MEG) monomers”, emphasis added). The conflict between the claims and specification leads to ambiguity as to the intended scope of the claim. In the interest of compact prosecution, “depolymerizing the PET in an ester…” of claim 1 is construed as if it stated “depolymerizing the PET into an ester…”.
Claim 1 recites “an etheroxide base of the sodium methoxide or potassium methoxide type”. The terminology “the sodium methoxide…” lacks antecedent basis. Also, it is unclear what species are encompassed by the genus “sodium methoxide or potassium methoxide type” as the language does not have a precise meaning in the art and is not defined/discussed within the specification. It is unclear what other etheroxide bases beyond sodium methoxide or potassium methoxide are meant to be encompassed by the term. See also MPEP 2173.05(b)(III)(E): The addition of the word "type" to an otherwise definite expression (e.g., Friedel-Crafts catalyst) extends the scope of the expression so as to render it indefinite. Ex parte Copenhaver, 109 USPQ 118 (Bd. Pat. App. & Inter. 1955).
Claim 1 recites “inorganic base of the sodium hydroxide or potassium hydroxide type”. The terminology “the sodium hydroxide…” lacks antecedent basis. Also, it is unclear what species are encompassed by the genus “sodium hydroxide or potassium hydroxide type” as the language does not have a precise meaning in the art and is not defined/discussed within the specification. It is unclear what other inorganic bases beyond sodium hydroxide or potassium hydroxide are meant to be encompassed by the term. See also MPEP 2173.05(b)(III)(E): The addition of the word "type" to an otherwise definite expression (e.g., Friedel-Crafts catalyst) extends the scope of the expression so as to render it indefinite. Ex parte Copenhaver, 109 USPQ 118 (Bd. Pat. App. & Inter. 1955).
As claims 2-15 depend from claim 1, they are rejected for the same issues discussed above.
Claim 2 recites “Methyl Ketone (MEK)”. However, “MEK” ordinarily denotes methyl ethyl ketone. It is unclear whether methyl ethyl ketone or some other ketone solvent is intended by the claim.
Claim 3 provides a structure of Formula (I) with a number “35” within. It is unclear what is meant to implied by the inclusion of “35”. Also, the structure of claim 3 does not appear to be complete as X is indicated to be only C or N.
As claim 4 depends upon claim 3, claim 4 is rejected for the same issue discussed above.
Claim 5 recites “wherein the inorganic base is selected from sodium or potassium methoxide, sodium hydroxide or potassium hydroxide”. However, claim 1 defines the “inorganic base” as “of the sodium hydroxide or potassium hydroxide type” and uses the terminology “etheroxide base” for methoxide bases. Since the listed methoxide types are not “of the sodium hydroxide or potassium hydroxide type”, the intended scope of the claim is unclear.
Claim 11 recites “wherein the amount of the bases is less than 5%”. It is unclear whether the 5% figure is meant to be wt%, vol%, or mol%. It is also unclear what the recited percentage is relative to (e.g. relative to weight of PET? Relative to the weight of depolymerization mixture?).
Claim 12 recites “wherein the amount of methanol is at least 5 times greater in molar ratio than the amount of PET”. It is unclear what method step the recitation pertains to as “methanol” is not introduced within claim 1. In the interest of compact prosecution, claim 12 is construed as if the monoalcohol of claim 1 is limited to methanol and the quantity relates to the depolymerization step.
Claim 15 recites “the DMT”, which lacks antecedent basis. Therefore, the intended scope of the claim is unclear.
Claim 16 recites “a step of depolymerizing the PET in an ester of terephthalate and monoethylene glycol (MEG)”, which literally suggests depolymerizing PET in a reaction mixture of terephthalate ester and monoethylene glycol. However, the specification appears to be descriptive of terephthalate ester and monoethylene glycol as products of the depolymerization process (see ¶ 14: “polyethylene terephthalate (PET) polymer into terephthalate and monoethylene glycol ester (MEG) monomers”, emphasis added). The conflict between the claims and specification leads to ambiguity as to the intended scope of the claim. In the interest of compact prosecution, “depolymerizing the PET in an ester…” of claim 1 is construed as if it stated “depolymerizing the PET into an ester…”.
Claim 16 recites “an etheroxide base of at least one of… sodium hydroxide, or potassium hydroxide”. However, sodium hydroxide and potassium hydroxide are not etheroxide bases. Accordingly, the intended scope of the claim is unclear.
As claims 17-20 depend from claim 16, they are rejected for the same issue discussed above.
Claim 17 recites “Methyl Ketone (MEK)”. However, “MEK” ordinarily denotes methyl ethyl ketone. It is unclear whether methyl ethyl ketone or some other ketone solvent is intended by the claim.
Claim 18 provides a structure of Formula (I) with a number “35” within. It is unclear what is meant to implied by the inclusion of “35”. Also, the structure of claim 18 does not appear to be complete as X is indicated to be only C or N.
Claim 20 recites the terminology “the inorganic base”, which lacks antecedent basis. Therefore, the intended scope of the claim is unclear.
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.
Claims 4, 19, and 20 are 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.
Claims 4 and 19 depend from claims 3 and 18 respectively, which contain Formula (I). However, the DBU, DBN, and TBD species do not appear to be within the scope of Formula (I) since there is no indication R can be alkylene and/or otherwise be connected to one another to form a heterocycle. Accordingly, claims 4 and 19 fail to include all of the limitations of the claim upon which it depends.
To the extent “the inorganic base” of claim 20 is referring to “the etheroxide base” of claim 16, claim 16 already indicates the etheroxide base is “at least one of sodium methoxide, potassium methoxide, sodium hydroxide, or potassium hydroxide”. Therefore, claim 20 fails to further limit the subject matter of the claim upon which it depends.
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.
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.
Claim(s) 1-20 is/are rejected under 35 U.S.C. 103 as being unpatentable over Medimagh (WO 2020/128218 A1) in view of Sharpe (US 2023/0030777 A1). As the cited WO publication is in a non-English language, a machine-translated version of the publication will be cited to.
The examiner has reviewed priority application 62/951,425 of Sharpe finds written support for the citations below.
Regarding Claims 1, 3-7, 16, and 18-20, Medimagh teaches methods of recycling PET comprising milling/grinding the PET into fragmented pieces, pretreating the fragmented pieces with solvent to facilitate depolymerization, and depolymerizing the PET into terephthalate ester and monoethylene glycol with monoalcohol and base such as sodium/potassium methoxide (¶ 26-30, 35). Embodiments are taught with 2 g PET relative to 15 mL (~ 12 g) of methanol and 560 mg of sodium methoxide to provide dimethyl terephthalate and ethylene glycol (¶ 76), construed as a catalytic amount of base and excess monoalcohol. White solid terephthalate ester is isolated via filtration (¶ 76), construed as powder.
Medimagh teaches depolymerizations at temperatures below 50 degrees C (¶ 29) and timeframes on the order of 30 minutes to 5 hours (Examples spanning ¶ 69-77). The disclosed temperature range overlaps that claimed. It would have been obvious to one of ordinary skill in the art to use a range within the claimed range because a reference may be relied upon for all that it would have reasonably suggested to one having ordinary skill the art and Medimagh suggests the claimed range. A person of ordinary skill would be motivated to use the claimed amount, based on the teachings of Medimagh. See MPEP 2123.
Medimagh differs from the subject matter claimed in that a combination of organic amidine/guanidine base with etheroxide/inorganic base is not described. Sharpe also pertains to the depolymerization of polyalkylene terephthalates with monoalcohol in the presence of base catalyst (Abstract). Sharpe teaches sodium methoxide, diazabicyclo[5.4.0]undec-7-ene (DBU), and triazabicyclodecene (TBD) were all known catalysts of the art that exhibit excellent depolymerization ability at reasonable catalyst loadings (¶ 29). It is well settled that it is prima facie obvious to combine two ingredients, each of which is targeted by the prior art to be useful for the same purpose. In re Crockett, 279 F.2d 274, 126 USPQ 186 (CCPA 1960). Ex parte Quadranti, 25 USPQ2d 1071 (Bd. Pat. App. & Inter. 1992). Also, case law holds that “it is prima facie obvious to combine two compositions each of which is taught by the prior art to be useful for the same purpose, in order to form a third composition to be used for the very same purpose.... [T]he idea of combining them flows logically from their having been individually taught in the prior art.” In re Kerkhoven, 626 F.2d 846, 850, 205 USPQ 1069, 1072 (CCPA 1980). As Sharpe indicates it was known in the art all of sodium methoxide, diazabicyclo[5.4.0]undec-7-ene (DBU), and triazabicyclodecene (TBD) are effective depolymerization catalysts, it would have been obvious to one of ordinary skill in the art to utilize combinations of suitable catalysts, inclusive of a combination of sodium methoxide with diazabicyclo[5.4.0]undec-7-ene (DBU) and/or triazabicyclodecene (TBD) to afford the predictable result of depolymerization ability at reasonable catalyst loadings.
Regarding Claims 2 and 17, Medimagh teaches pretreating with solvents such as DMAC, DMF, and/or MEK (¶ 47).
Regarding Claim 8, Medimagh teaches ethanol can be used as monoalcohol (¶ 53). As monoalcohol solvent is used in excess, a diethyl terephthalate product would naturally arise over the course of depolymerization.
Regarding Claims 9 and 10, Medimagh teaches monoalcohols such as methanol, ethanol, or any linear/branched alcohol with a hydrocarbon chain can be used (¶ 53). Although Medimagh does not explicitly state the species propanol and butanol, Medimagh makes clear any linear alcohol with a hydrocarbon chain can be used. It is the examiner’s position that one would expect similar beneficial results with compounds having only additional one or two –CH2– groups in view of the teachings of Medimagh. Case laws holds that homologs (compounds differing regularly by the successive addition of the same chemical group, e.g,. by –CH2– groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties. In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977). In view of such, it would have been obvious to one of ordinary skill in the art that linear homologues such as propanol or butanol can be used within the protocols of Medimagh with a reasonable expectation of similar characteristics, namely the ability to arrive at terephthalate and monoethylene glycol depolymerization products. As Medimagh teaches excess of mono-alcohol is used, the formation of either dipropyl terephthalate or dibutyl terephthalate would naturally arise.
Regarding Claim 11, Medimagh teaches embodiments with 2 g PET relative to 15 mL (~ 12 g) of methanol and 560 mg of sodium methoxide (¶ 76), corresponding to roughly 0.56 / 14.56 = 3.8 wt%.
Regarding Claim 12, Medimagh teaches embodiments with 2 g PET (~ 0.01 mol) relative to 15 mL (~ 12 g; ~ 0.37 mol) of methanol is used (¶ 76), which is in excess of 5x greater in molar ratio.
Regarding Claim 13, Medimagh teaches depolymerizations timeframes such as 1 hr 30 min (¶ 76). Medimagh teaches temperatures below 50 degrees C (¶ 29). While just outside the range claimed, a prima facie case of obviousness exists where the claimed ranges or amounts do not overlap with the prior art but are merely close. MPEP 2144.05(I). In view of the cited case law therein, it would have been obvious to one of ordinary skill in the arts that temperatures just outside the range of Medimagh (e.g. 50 degrees C) can be used since the value is so close that there would be expectation that the reaction would still afford the predictable result of depolymerized PET.
Alternatively, to the extent Medimagh differs from the subject matter claimed with respect to depolymerization temperature used, Sharpe teaches it was known in the art the temperature used for depolymerization should be high enough in order to effect depolymerization while also low reaction temperatures at which the catalyst is active is generally preferable (¶ 35; Claim 1). Case law holds that “discovery of an optimum value of a result effective variable in a known process is ordinarily within the skill of the art.” See In re Boesch, 617 F.2d 272, 205 USPQ 215 (CCPA 1980). In view of this, it would have been obvious to one of ordinary skill in the art to discover optimal or workable depolymerization temperatures within the scope of the present claims so as to produce desirable reaction rates/catalysis while avoiding costs associated with excessive heating.
Regarding Claim 14, Medimagh teaches washing the pretreated pieces with alcohol and drying prior to depolymerizing (¶ 76).
Regarding Claim 15, Medimagh teaches recovering DMT via filtration of the reaction medium and washing a cake obtained (¶ 76).
Claim(s) 1-20 is/are rejected under 35 U.S.C. 103 as being unpatentable over Medimagh (WO 2020/128218 A1) in view of Pham (Green Chem. 2021, 23, 511). As the cited WO publication is in a non-English language, a machine-translated version of the publication will be cited to.
Pham has a publication date of 12/8/2020. Applicant cannot rely upon the certified copy of the foreign priority application to overcome this rejection because a translation of said application has not been made of record in accordance with 37 CFR 1.55. When an English language translation of a non-English language foreign application is required, the translation must be that of the certified copy (of the foreign application as filed) submitted together with a statement that the translation of the certified copy is accurate. See MPEP §§ 215 and 216.
Regarding Claims 1, 3-7, 16, and 18-20, Medimagh teaches methods of recycling PET comprising milling/grinding the PET into fragmented pieces, pretreating the fragmented pieces with solvent to facilitate depolymerization, and depolymerizing the PET into terephthalate ester and monoethylene glycol with monoalcohol and base such as sodium/potassium methoxide (¶ 26-30, 35). Embodiments are taught with 2 g PET relative to 15 mL (~ 12 g) of methanol and 560 mg of sodium methoxide to provide dimethyl terephthalate and ethylene glycol (¶ 76), construed as a catalytic amount of base and excess monoalcohol. White solid terephthalate ester is isolated via filtration (¶ 76), construed as powder.
Medimagh teaches depolymerizations at temperatures below 50 degrees C (¶ 29) and timeframes on the order of 30 minutes to 5 hours (Examples spanning ¶ 69-77). The disclosed temperature range overlaps that claimed. It would have been obvious to one of ordinary skill in the art to use a range within the claimed range because a reference may be relied upon for all that it would have reasonably suggested to one having ordinary skill the art and Medimagh suggests the claimed range. A person of ordinary skill would be motivated to use the claimed amount, based on the teachings of Medimagh. See MPEP 2123.
Medimagh differs from the subject matter claimed in that a combination of organic amidine/guanidine base with etheroxide/inorganic base is not described. Pham also pertains to the depolymerization of polyalkylene terephthalates with monoalcohol in the presence of base catalyst (Abstract). Pham teaches potassium methoxide and triazabicyclodecene (TBD) were both known catalysts of the art that exhibit excellent depolymerization ability (Figure 2; Section 3.2). It is well settled that it is prima facie obvious to combine two ingredients, each of which is targeted by the prior art to be useful for the same purpose. In re Crockett, 279 F.2d 274, 126 USPQ 186 (CCPA 1960). Ex parte Quadranti, 25 USPQ2d 1071 (Bd. Pat. App. & Inter. 1992). Also, case law holds that “it is prima facie obvious to combine two compositions each of which is taught by the prior art to be useful for the same purpose, in order to form a third composition to be used for the very same purpose.... [T]he idea of combining them flows logically from their having been individually taught in the prior art.” In re Kerkhoven, 626 F.2d 846, 850, 205 USPQ 1069, 1072 (CCPA 1980). As Pham indicates it was known in the art all of potassium methoxide and triazabicyclodecene (TBD) are effective catalysts, it would have been obvious to one of ordinary skill in the art to utilize combinations of suitable catalysts, inclusive of a combination of potassium methoxide and triazabicyclodecene (TBD) to afford the predictable result of depolymerization ability.
Regarding Claims 2 and 17, Medimagh teaches pretreating with solvents such as DMAC, DMF, and MEK (¶ 47).
Regarding Claim 8, Medimagh teaches ethanol can be used as monoalcohol (¶ 53). As monoalcohol solvent is used in excess, a diethyl terephthalate product would naturally arise over the course of depolymerization.
Regarding Claims 9 and 10, Medimagh teaches monoalcohols such as methanol, ethanol, or any linear/branched alcohol with a hydrocarbon chain can be used (¶ 53). Although Medimagh does not explicitly state the species propanol and butanol, Medimagh makes clear any linear alcohol with a hydrocarbon chain can be used. It is the examiner’s position that one would expect similar beneficial results with compounds having only additional one or two –CH2– groups in view of the teachings of Medimagh. Case laws holds that homologs (compounds differing regularly by the successive addition of the same chemical group, e.g,. by –CH2– groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties. In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977). In view of such, it would have been obvious to one of ordinary skill in the art that linear homologues such as propanol or butanol can be used within the protocols of Medimagh with a reasonable expectation of similar characteristics, namely the ability to arrive at terephthalate and monoethylene glycol depolymerization products. As Medimagh teaches excess of mono-alcohol is used, the formation of either dipropyl terephthalate or dibutyl terephthalate would naturally arise.
Regarding Claim 11, Medimagh teaches embodiments with 2 g PET relative to 15 mL (~ 12 g) of methanol and 560 mg of sodium methoxide (¶ 76), corresponding to roughly 0.56 / 14.56 = 3.8 wt%.
Regarding Claim 12, Medimagh teaches embodiments with 2 g PET (~ 0.01 mol) relative to 15 mL (~ 12 g; ~ 0.37 mol) of methanol is used (¶ 76), which is in excess of 5x greater in molar ratio.
Regarding Claim 13, Medimagh teaches depolymerizations timeframes such as 1 hr 30 min (¶ 76). Medimagh teaches temperatures below 50 degrees C (¶ 29). While just outside the range claimed, a prima facie case of obviousness exists where the claimed ranges or amounts do not overlap with the prior art but are merely close. MPEP 2144.05(I). In view of the cited case law therein, it would have been obvious to one of ordinary skill in the arts that temperatures just outside the range of Medimagh (e.g. 50 degrees C) can be used since the value is so close that there would be expectation that the reaction would still afford the predictable result of depolymerized PET.
Alternatively, to the extent Medimagh differs from the subject matter claimed with respect to depolymerization temperature used, Pham teaches it was known in the art the temperature used for depolymerization should be high enough in order to effect depolymerization while also low reaction temperatures at which the catalyst is active is generally preferable (Abstract). Case law holds that “discovery of an optimum value of a result effective variable in a known process is ordinarily within the skill of the art.” See In re Boesch, 617 F.2d 272, 205 USPQ 215 (CCPA 1980). In view of this, it would have been obvious to one of ordinary skill in the art to discover optimal or workable depolymerization temperatures within the scope of the present claims so as to produce desirable reaction rates/catalysis while avoiding costs associated with excessive heating.
Regarding Claim 14, Medimagh teaches washing the pretreated pieces with alcohol and drying prior to depolymerizing (¶ 76).
Regarding Claim 15, Medimagh teaches recovering DMT via filtration of the reaction medium and washing a cake obtained (¶ 76).
Conclusion
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/STEPHEN E RIETH/Primary Examiner, Art Unit 1759