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 .
Status of the Claims
A preliminary amendment to the claims has not been filed. Thus claims 1-20 filed on 04/23/2024 are currently pending and are under examination.
Claim Objections
Claim 7 is 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 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 12 and 16 is 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.
Regarding claim 12, the claimed amount of 100 mol% of each components renders the claim vague and indefinite as the recited components are not polyesters per se and thus it is unclear how a polyester composition can contain 100 mol%. What would be the amount of polyester? Furthermore, the mole % of each is vague and indefinite as it is not clear what the mole % is based upon. Due to the unclear scope, the claim will not be examined for patentability.
Regarding claim 16, the parenthetical limitation "FASCAT 4102" renders the claim indefinite because it is unclear whether the limitation(s) is part of the claimed invention. See MPEP § 2173.05(d).
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.
Claim(s) 1-4, 6, 9, 11 and 13-20 are rejected under 35 U.S.C. 103 as being unpatentable over Kim (Kim, B-K. et al. “Chemical Recycling of Poly(Ethylene Terephthalate) Using a New Hybrid Process” J. Chem. Eng. Jpn. 41, 9, pp. 923-928, 2008; cited in IDS 07/07/2025) in view of Patent number US5,672,729 (US’729).
Regarding claims 1, 9, 11 and 17-18, Kim teaches in Table 1 and Fig. 3 a process for recovering dimethyl terephthalate (DMT) from Poly(Ethylene Terephthalate) (PET) composition, comprising: exposing a first polyester composition to a first composition comprising ethylene glycol (EG) and methanol in a first reaction vessel under depolymerization conditions to provide a first mixture, the first mixture comprising the depolymerization product, and wherein the depolymerization conditions comprise a temperature of 473.15–533.15 K (200° C.-260° C.) and a pressure of 0.5-2.0 MPa (about 5 atm to 19 atm); exposing the first mixture to an alcohol composition (methanol) to provide a second mixture, the second mixture comprising DMT; and separating DMT by solid-liquid separation to provide a DMT solid component and a filtrate.
Regarding claim 2, the limitation “wherein at least a portion of the methanol was recovered from …” is a product by process claim language as a result of methanol product. The product by process limitation is not limited to the manipulations of the recited steps for preparing methanol, but only to the structure implied by the steps, in this case, only to methanol. See MPEP § 2113:
"[E]ven though product-by-process claims are limited by and defined by the process, determination of patentability is based on the product itself. The patentability of a product does not depend on its method of production. If the product in the product-by-process claim is the same as or obvious from a product of the prior art, the claim is unpatentable even though the prior product was made by a different process." In re Thorpe, 777 F.2d 695, 698, 227 USPQ 964, 966 (Fed. Cir. 1985) (citations omitted) (Claim was directed to a novolac color developer. The process of making the developer was allowed. The difference between the inventive process and the prior art was the addition of metal oxide and carboxylic acid as separate ingredients instead of adding the more expensive pre-reacted metal carboxylate. The product-by-process claim was rejected because the end product, in both the prior art and the allowed process, ends up containing metal carboxylate. The fact that the metal carboxylate is not directly added, but is instead produced in-situ does not change the end product.). Furthermore, "[b]ecause validity is determined based on the requirements of patentability, a patent is invalid if a product made by the process recited in a product-by-process claim is anticipated by or obvious from prior art products, even if those prior art products are made by different processes." Amgen Inc. v. F. Hoffman-La Roche Ltd., 580 F.3d 1340, 1370 n 14, 92 USPQ2d 1289, 1312, n 14 (Fed. Cir. 2009). See also Purdue Pharma v. Epic Pharma, 811 F.3d 1345, 117 USPQ2d 1733 (Fed. Cir. 2016). However, in the context of an infringement analysis, a product-by-process claim is only infringed by a product made by the process recited in the claim. Id. at 1370 ( "a product in the prior art made by a different process can anticipate a product-by-process claim, but an accused product made by a different process cannot infringe a product-by-process claim" ).
Furthermore, because the process steps do not appear to impart distinctive structural characteristic to the final methanol product, the process steps are not given patentable weight. See MPEP § 2113:
The structure implied by the process steps should be considered when assessing the patentability of product-by-process claims over the prior art, especially where the product can only be defined by the process steps by which the product is made, or where the manufacturing process steps would be expected to impart distinctive structural characteristics to the final product. See, e.g., In re Garnero, 412 F.2d 276, 279, 162 USPQ 221, 223 (CCPA 1979) (holding "interbonded by interfusion" to limit structure of the claimed composite and noting that terms such as "welded," "intermixed," "ground in place," "press fitted," and "etched" are capable of construction as structural limitations). See also In re Nordt Dev. Co., 881 F.3d 1371,1375-76, 125 USPQ2d 1817, 1820 (Fed. Cir. 2018)(holding "the specification demonstrates that ‘injected molded’ connotes an integral structure," and discussing several cases since Garnero that held "limitations to convey structure even when they also describe a process of manufacture").
Regarding claim 3, Kim teaches that the product (second mixture) consists of DMT, EG and methanol (page 924, 2nd para.), and thus the filtrate after the separation of solid DMT would necessarily consist of EG and methanol.
Regarding claim 4, Kim fails to teach exposing a second polyester composition to at least a portion of the filtrate in the first reaction vessel under the depolymerization conditions to produce one or more second depolymerization product. However, as indicated above, since the filtrate consists of EG and methanol, and since the depolymerization process uses the two components, a skilled artisan would have been motivated in re-using the filtrate to depolymerize additional PET (polyester) composition.
Regarding claim 13, since the application uses the same PET as a polyester composition as that of Kim, the PET of Kim would necessarily have the claimed viscosity.
Regarding claim 14, Kim teaches that the PET waste used in this experiment was commercial chip produced by Sepung Co., which includes a small amount of contaminants from caps and labels.
Regarding claim 16, the depolymerization in Kim is conducted in the presence of zinc acetate.
Regarding claim 20, Kim is silent that the depolymerization product comprises monomers, oligomers, or a combination thereof, and wherein the oligomers exhibit a degree of polymerization of from 2 to 10. However, since the reference teaches the same depolymerization process as instantly claimed, the depolymerization product in Kim would necessarily comprise monomers, oligomers, or a combination thereof, and wherein the oligomers exhibit a degree of polymerization of from 2 to 10.
Regarding claim 1, Kim fails to teach cooling the first mixture to a temperature of 150° C. or below; exposing the at least a portion of the first mixture to an alcohol composition and an alcoholysis catalyst under conditions including a temperature of from 23° C. to 90° C., and a pressure of from 1 atm to 2 atm for 0.5 hours to 5 hours to provide a second mixture. The deficiencies are, however, cured by US’729.
Regarding claims 1 and 6, US’729 teaches a process for improving the yield of difunctional ester in a process of recovering monomer components from condensation-type polyester resins such as polyethylene terephthalate by converting terephthalyl monomers and oligomers present in ethylene glycol still bottoms to terephthalate diester, such as dimethyl terephthalate (DMT). The process comprises:
a) contacting the first mixture with a second mixture comprising an alcohol and an alkali metal hydroxide at a temperature in the range of from 0° C. to the boiling point
of the alcohol (which is methanol with a b.pt. 64.7° C).and a pressure in the range of 0 psig to 100 psig (about 0-6.8 atm.),
b) allowing the mixture formed in step a) to react for a period of from 0.5 to 30 minutes, and
c) separating the terephalate diester formed in step b) from the liquid glycol residue.
Thus, since the alcoholysis in US’729 is conducted at lower temperature than the depolymerization step of Kim, the polymerization mixture would have to be cooled to a temperature of 0° C. to 64.7° C.
Regarding claim 15, the solid component comprises DMT at a purity of 90% (col. 7).
Regarding claim 17, since Kim teaches that PET comprises contaminants, a skilled artisan would have been motivated in removing these contaminants after depolymerization but prior to alcoholysis step of US’729 with a reasonable expectation of success in obtaining DMT at an optimal purity.
Regarding claim 19, US’729 teaches that the preferred alkalimetal hydroxides are sodium hydroxide and potassium hydroxide.
The alcoholysis reaction of US’729 is conducted at a lower reaction temperature than that of Kim (see Table 1), and US’729 produces DMT at a high purity. As such, a skilled artisan would have been motivated in using the alcoholysis of US’729 in the process of Kim with a reasonable expectation of success in obtaining DMT at an optimal purity.
It would thus have been prima facie obvious to a skilled artisan before the effective filing date of the instant invention to conduct a process for recovering one or more dialkyl terephthalates from a polyester composition, comprising: exposing a first polyester composition to a first composition comprising one or more glycols and methanol in a first reaction vessel under depolymerization conditions to provide a first mixture, the first mixture comprising one or more first depolymerization products, and wherein the depolymerization conditions comprise a temperature of from 150° C. to 260° C. and a pressure of 10 atm to 70 atm; cooling at least a portion of the first mixture to a temperature of 150° C. or below; exposing the at least a portion of the first mixture to an alcohol composition and an alcoholysis catalyst under conditions including a temperature of from 23° C. to 90° C., and a pressure of from 1 atm to 2 atm for 0.5 hours to 5 hours to provide a second mixture, the second mixture comprising one or more dialkyl terephthalates; and separating at least a portion of the one or more dialkyl terephthalates by solid-liquid separation to provide a dialkyl terephthalate solid component and a filtrate in view of the teachings of Kim and US’729.
Claims 5, 8 and 10 are rejected under 35 U.S.C. 103 as being unpatentable over Kim (Kim, B-K. et al. “Chemical Recycling of Poly(Ethylene Terephthalate) Using a New Hybrid Process” J. Chem. Eng. Jpn. 41, 9, pp. 923-928, 2008; cited in IDS 07/07/2025) in view of Patent number US5,672,729 (US’729) as applied to claims 1-4, 6, 9, 11 and 13-20 above, and further in view of Patent number US5,952,520 (US’520).
The teachings of Kim and US’729 have been set forth above. The references, however, fail to teach or suggest the limitations of claims 5, 8 and 10. The deficiencies are cured by US’520.
US’520 teaches a method for producing DMT by first depolymerizing PET with glycol and methanol in the presence of zinc acetate catalyst followed by methanolysis to produce DMT.
Regarding claim 5, 33 g of diethylene glycol, 17 g of triethylene glycol and 210 g of methanol have been used in the depolymerization and thus the weight ratio of the glycols to methanol is 1:4.2 (Example 2).
Regarding claim 8, 264 g of PET has been used (Example 2) and the weight ration of the glycols to the polyester is 1.2:1.
Regarding claim 10, 100 parts of methanol per 1 part of methylhydroxyethyl terephthalate have been used in the second step and thus it would be within the purview of a skilled artisan to determine the optimal weight ratio of methanol to PET in order to provide an optimal yield of DMT.
It would thus have been prima facie obvious to a skilled artisan before the effective filing date of the instant invention to conduct a process for recovering one or more dialkyl terephthalates from a polyester composition, comprising: exposing a first polyester composition to a first composition comprising one or more glycols and methanol in a first reaction vessel under depolymerization conditions to provide a first mixture, the first mixture comprising one or more first depolymerization products, and wherein the depolymerization conditions comprise a temperature of from 150° C. to 260° C. and a pressure of 10 atm to 70 atm; cooling at least a portion of the first mixture to a temperature of 150° C. or below; exposing the at least a portion of the first mixture to an alcohol composition and an alcoholysis catalyst under conditions including a temperature of from 23° C. to 90° C., and a pressure of from 1 atm to 2 atm for 0.5 hours to 5 hours to provide a second mixture, the second mixture comprising one or more dialkyl terephthalates; and separating at least a portion of the one or more dialkyl terephthalates by solid-liquid separation to provide a dialkyl terephthalate solid component and a filtrate; wherein a weight ratio of the amount of the one or more glycols relative to the amount of the methanol in the first reaction vessel is 1:20 to 100:1, wherein, during the exposing a first polyester composition to a first composition comprising one or more glycols and methanol in a first reaction vessel under depolymerization conditions, a weight ratio of the one or more glycols to the first polyester composition is in a range of about 1:9 to about 9:1, and wherein a weight ratio of the alcohol composition to the first polyester composition can be in a range of about 2:1 to about 10:1 in view of the teachings of Kim, US’729 and US’520.
Allowable Subject Matter
The subject matter of claim 7 is free of prior art. The closest prior art references have been set forth above, however they fail to teach or suggest the process as further comprising separating at least a portion of the one or more first depolymerization products in the first mixture from an insoluble component in the first mixture, wherein the separating occurs at a temperature of from 50° C. to 150° C.
Conclusion
Claims 1-6 and 8-20 are rejected and no claims are allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to MEDHANIT W BAHTA whose telephone number is (571)270-7658. The examiner can normally be reached Monday-Friday 8am-5pm.
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/MEDHANIT W BAHTA/Primary Examiner, Art Unit 1692
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