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
Claim Status
Claims 1, 3-15 and 20-21 are pending. Claims 1, 3-15 and 20-21 are under examination. Claims 1, 3-15 and 20-21 are rejected. No claims allowed.
Filing Receipt
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Response to Amendments/Arguments
Applicant's amendments and arguments filed 07/24/2026 are acknowledged and have been fully considered. The Examiner has re-weighed all the evidence of record. Any rejection and/or objection not specifically addressed below in original or modified form is herein withdrawn.
Withdrawn Rejections
The nonstatutory double patenting rejection of claims 1, and 3-15 over claims 1, 3-9, and 11-17 of US Patent 12,441,675 (18/726,819) in view of Cruz-Gomez et al., Sun et al., Toida et al. and Sim et al. in the non-final mailed 01/08/2026 is withdrawn. See approved signed terminal disclaimer filed 07/24/2026 which has overcome the rejection.
Response to Arguments
Applicant's arguments filed 07/24/2026 have been fully considered but they are not persuasive.
Applicant points to the Declaration under 37 C.F.R. § 1.132 by Hee-11 Chae on pages 10-11 of the arguments and states the following.
“Data showing that that the use of an alcohol having 4 to 14 carbon atoms in the alcoholysis of the present invention produce unexpected results when compared to the
closest prior art, Cruz-Gomez. The data presented in the Declaration shows that the use of C4-C14 alcohols provided significantly higher TPA purity with lower impurities when compared to the use of methanol or ethanol. That evidence is unexpected from the teachings of the prior art”.
Examiner’s Response:
The claims are not commensurate in scope with the unexpected result for reasons discussed below.
Table A of the Declaration page 2 does show an approximate 5% increase in
purity with the use of the current alcohols over methanol and ethanol. The prior art
Cruz-Gomez et al. (US Patent 5,948,934, Patent date 09-1999) exemplifies methanol in the working examples and teach alcohols useful for the present process can have 4 carbon atoms and can have an alkyl chain of n-butyl (column 3, lines 10-20). Thus a working example of n-butanol or for that matter a 4 carbon alcohol is lacking.
Cruz-Gomez et al. does not teach the improved purities when utilizing the current alcohols having 4 to 14 carbon atoms to those of methanol and ethanol.
However, Toida et al. (USPGPub 2010/0298524, Published 11-2010) was found to teach the following impurities and the respective concentrations with the hydrolysis of dimethyl terephthalate to yield the terephthalic acid and methanol (par. 29-30). “the amount of impurities in the resultant terephthalic acid from the reaction is preferably 1,000 ppm or less and is more preferably controlled such that the total amount of dimethyl terephthalate and monomethyl terephthalate contained as impurities becomes 1,000 ppm or less” (par. 30). Toida et al. teach larger alkyl esters of terephthalate which overlap the current alcohol carbon lengths, butyl, hexyl, etc. (par. 30).
The above impurity concentrations were obtained in the hydrolysis of dimethyl terephthalate to obtain the terephthalic acid (par. 30). Toida et al. goes on to teach the removal of the methanol from the hydrolysis reaction shifts the reaction equilibrium to the “product-increase side, whereby a high reaction rate can be realized” (par. 30).
It is noted that dimethyl terephthalate and monomethyl terephthalate at 1,000 ppm or less as taught by Toida et al. are calculated to be 0.01% (10,000 ppm = 1%) or less. These percent concentrations taught by Toida et al. are below impurity levels in Table A of the Declaration last two columns on the right, regardless of the alcohols utilized.
From the above comparison of current impurities to those in the prior art, the method of obtaining the current terephthalic acid in conjunction with the alcohols plays a defining role with respect to the concentration of impurities and not necessarily the alcohol alone.
The method utilized in the Declaration is one of recrystallization and at least layer separation (page 3 of the Declaration). The Declaration recites the solubility of organic materials in the current alcohols result in an excellent purification effect as opposed to ethanol and methanol (page 3). To achieve the excellent purification, a method of recrystallization and at least layer separation is needed (page 3 of the Declaration).
The current claims are not directed to a layer separation and/or a recrystallization step. The practitioner of the current claims would not achieve the excellent purification effect. The claims lack the critical method steps, layer separation and recrystallization that yield the high purities. Therefore the claims are not commensurate in scope with the unexpected result.
Note: the claims use comprising language with respect to a hydrolysis step. This would include the hydrolysis step and workup in the current declaration and the hydrolysis steps of Toida et al. and additionally others.
Response to the Declaration
The declaration and Exhibit A filed 07/24/2026 have been fully considered.
Per the above arguments in the examiner’s response, the declaration points to an improved purity of the current product when utilizing the current alcohols. See Table A page 2. However, the declaration fails to establish the method steps as written in the current claims result in the improved purity. The declaration recites the solubility of organic materials in the current alcohols result in an excellent purification effect during a recrystallization and at least layer separation step. See immediately below.
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From the above, steps of a layer separation and recrystallization (most likely a crystallization) in conjunction with the current alcohols is required to yield the purported unexpected purities. The current claims have no such steps.
Additionally, the prior art was shown to yield comparable purities with the use of methanol and overlapping alcohols as currently claimed. The declaration has not addressed these purities in the prior art.
For the reasons stated above the obviousness rejection is modified/maintained as set forth below.
Claim Interpretation
Per the specification page 5,
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Therefore, unless otherwise indicated the numerical value of 28 bar is interpreted to be about 28 bar. Values above 28 bar are encompassed by 28 bar.
The specification does not define “about” nor the verbiage to designate the negative proviso of “about”. The negative proviso of “about” is only exemplified by the phrase “unless otherwise indicated”. Meaning the phrase “at a pressure of 1 bar to 28 bar” in claim 1, does not explicitly or implicitly imply hard boundaries so that numerical values outside of the claimed range are excluded.
Modified Rejections
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, 3-13, and 21 is/are rejected under 35 U.S.C. 103 as being unpatentable over Cruz-Gomez et al. (US Patent 5,948,934, Patent date 09-1999), Sun et al. (KR20200046198, Published 05-2020. Cited in IDS filed 07/08/2024) and Toida et al. (USPGPub 2010/0298524, Published 11-2010) as evidence by Pham et al. (Low-energy catalytic methanolysis of poly(ethyleneterephthalate), Green Chemistry, 23, pp. 511-525, Published 2021) and Ashenhurst (Master Organic Chemistry, pp. 1-33, Published 03-2021). The modifications to this rejection were necessitated by amendment.
Scope of the Prior Art
Cruz-Gomez et al. teach the methanolysis (alcoholysis) of used polyethylene
terephthalate (PET) to prepare a product mixture comprising solids, methanol, glycol and dimethyl terephthalate (DMT). The DMT is more broadly a dialkyl aromatic ester (DAAE) (Examples 1-2).
Cruz-Gomez et al. goes on to teach the preparation of a homogeneous hot solution from the product mixture by adding methanol, heating and stirring the product mixture (Example 2).
Next, Cruz-Gomez et al. teach filtration of the homogeneous hot solution and separating several solid insoluble impurities to obtain a clear solution (Example 2).
The clear solution was concentrated to recover methanol, and cooled to prepare
suspended solids. The solids being pure DMT. The mother liquid from the DMT is
distilled to remove water methanol and monoethylene glycol (Example 2).
Concerning the hydrolysis, Cruz-Gomez et al. teach reacting the solid DMT with water to prepare the current terephthalic acid (TPA) (Example 3).
Concerning currently claimed R1 variable and the number of carbons being 4, Cruz-Gomez et al. teach alcohols useful for the present process can have 4 carbon atoms and can have an alkyl chain of n-butyl (column 3, lines 10-20).
Concerning claim 3, Cruz-Gomez et al. teach 50 to 100 g of crushed bottle PET, 150 to 300g of methanol (Example 1) or 100:300 or 1:3. This overlaps the ratio of 1:1 to 1:10 waste PET to alcohol.
Concerning claim 4, Cruz-Gomez et al. teach 30 to 100 minutes, temperatures from 25 to 240° C and pressures of 6.5 MPa to 5.5 MPa or 65 Bar to 55 Bar (Example 1). Cruz-Gomez et al. teach pressures of 3.0 to 10 MPa or 30 Bar to 100 Bar (claim 4 of Cruz-Gomez et al.).
The immediately above times, temperatures and pressures overlap the claimed ranges. Due to the claimed pressure range allowing for pressures above 28 bar and/or Cruz-Gomez et al. teaching about 30 bar to 100 bar, overlap of the claimed and taught pressures exist.
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Note: high pressures occur during the use of methanol due to the low boiling point of methanol and the reaction temperature employed as evidence by Pham et al. “However, current commercial technologies still favor high reaction temperatures, which lead to high pressure due to the low boiling point of methanol” (p. 514 left column). Thus, boiling point and reaction pressures are inversely related.
Concerning claim 6, Cruz-Gomez et al. teach reuse of the alcohol acquired by distillation. (column 3, lines 55-64).
Concerning claim 8 and 9, Cruz-Gomez et al. teach zinc acetate 0.010 to 0.100 g to 50 to 100g of PET (Example 1). This reads on Zn2+ and acetate ion. 10,000 ppm being 1%, 10 ppm being 0.001%. 0.01% of 100g is 0.01 grams. This overlaps the claimed range.
Concerning claim 12, Cruz-Gomez et al. teach 250C (Example 3). This overlaps the claimed range.
Ascertaining the Difference
Cruz-Gomez et al. does not teach the acid hydrolysis occurring with a liquid composition comprising a compound represented by Formula 1 wherein R is greater than 4 or the purification of a liquid composition.
Secondary Reference
Sun et al. teach the isolation of liquid bis(2-ethylhexyl terephthalate) (DOTP) from an alcoholysis reaction mixture of PET (Examples 1-7). R1 is 8.
Sun et al. teach filtering the unreacted PET component from the reaction result
through a filtration device (p. 4 of 9). This overlaps the filtering teachings of Cruz-Gomez et al.
Sun et al. teach the recovery step of dioctyl terephthalate may further include (iv) a process of decolorizing the organic layer distilled in step (iii) using a decoloring agent, wherein the decoloring agent is activated carbon, activated clay, diatomaceous earth or a combination thereof, but is not limited thereto (p. 4 of 9). Sun et al. teach the use of 20 grams of activated carbon (p. 6 of 9). (current purification claims 10-11)
Sun et al. teach isolation steps of distillation and extraction for the recovery of 2-ethylhexanol and ethylene glycol (Examples 1-7).
Sun et al. teach the following benefits of the alcoholysis of PET (p. 1 of 9). Sun et al. teach “The object of the present invention is to obtain dioctyl terephthalate and antifreeze with high added value from PET at the same time in high yields, thereby providing excellent process efficiency and economy, and also recycling PET material waste in the form of films, bottles, and plastic containers. Therefore, it is to
provide an environmentally friendly manufacturing method”.
Concerning the claimed pressures, Sun et al. teach room pressure is utilized when performing alcoholysis on PET when using 2-ethylhexanol which has a boiling point of 183C. Room pressure is approximately 1 bar (Examples).
Note: the boiling point of methanol is lower than 2-ethylhexanol as evidence by
Ashenhurst (page 4 of 33). Ashenhurst teach lower molecular weight alcohols have lower boiling points (page 4 of 33). Hence, methanol/butanol has a lower boiling point than 2-ethylhexonal.
Note: high pressures occur during the use of methanol due to the low boiling point of methanol and the reaction temperature employed as evidence by Pham et al. “However, current commercial technologies still favor high reaction temperatures, which lead to high pressure due to the low boiling point of methanol” (p. 514 left column). Thus, boiling point and reaction pressures are inversely related.
Concerning claim 7, see example 1 wherein ethylene glycol flowed out to the distillation recovery tube.
The above teachings render Sun et al. analogous art to the invention.
Additional teachings of Sun et al. are as follows. Sun et al. teach yields of 98% in Example 5. Example 5 was run as Example 1. Thus room pressures were utilized.
Toida et al. broadly teach “terephthalic acid produced by the hydrolysis of a dialkyl terephthalate (DAT) (par. 18). Toida et al. teach DAT’s having greater than 4 carbon atoms in the alkyl arm of the esters being capable of hydrolysis (par. 29). Toida et al. teach “dialkyl terephthalic acid includes dimethyl terephthalate, diethyl terephthalate, dipropyl terephthalate, dibutyl terephthalate and dihexyl terephthalate” (R1 is 6). This teaching is interpreted to be an open ended listing of DAT’s. Six carbons
overlaps the amount of carbons in new claim 21
The above teachings render Toida et al. analogous art to the invention. The teachings of Toida et al. overlap with the teachings of Cruz-Gomez et al. with respect to the hydrolysis of DAT’s having 1-4 carbon atoms.
Obviousness
It would have been prima facie obvious for an ordinary artisan before the effective filing date of the claimed invention to have combined the teachings of Cruz-Gomez et al. and Sun et al. to arrive at the invention with a reasonable expectation of success. For example, it would have been prima facie obvious for an ordinary artisan to have utilized n-butanol in place of methanol in the process taught Cruz-Gomez et al. to arrive at the current invention wherein R1 is 4 carbons. The ordinary artisan would have done so with a reasonable expectation of success because Cruz-Gomez et al. teach the use of n-butanol (column 3, lines 10-20).
The claimed liquid composition (liquid dibutyl terephthalate (DBT)) is a property of the dialkyl terephthalate (DAT). Utilizing longer chain DAT’s allows for the DAT’s to be liquid. See Sun et al. Moreover, isolation of the liquid DAT’s from glycerol and the alcohol are taught by Sun et al.
Upon isolation of the DBT by the methods of Cruz-Gomez et al. and Sun et al., the DBT would have been a liquid at room temperature.
The ordinary artisan would have had a reasonable expectation of success trying
the ever-increasing alkyl lengths of 4 and greater for two reasons: 1) isolation of the
DAT from the PET alcoholysis compositions comprising glycol and alcohol are shown to
occur and 2) hydrolysis of the DAT’s having alkyl groups of 4 and/or more carbons are shown to occur (Toida et al. par. 18 and 29). The ordinary artisan would have looked to the teachings of Sun et al. because both prior art references teach alcoholysis of PET and Sun et al. teach the benefits of the alcoholysis of PET. The ordinary artisan would have looked to the teachings of Toida et al. because Sun et al. and Toida et al. teach the hydrolysis of DAT’s having 1-4 carbon atoms.
Concerning the claimed pressures, these would have occurred due to the boiling points of the alcohol. Lower boiling point alcohols necessarily create higher pressures in the claimed alcoholysis with a constant temperature. Moreover, lower molecular weight alcohols having lower boiling points necessarily generate higher pressures with a constant temperature. This relationship establishes molecular weight of the alcohol to be a result effective variable. The ordinary artisan understanding the above relationships would have arrived at the current pressures through routine experimentation.
Additionally, the ordinary artisan knowing that the room pressure leads to yields of 98% in Example 5 of Sun et al., would have adjusted the temperature and pressures of the alcoholysis reactions to arrive at optimal yields.
Concerning claims 3 and 4, MPEP 2144.05 I.: “In the case where the claimed ranges “overlap or lie inside ranges disclosed by the prior art” a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976).”
Additionally, the ordinary artisan would have arrived at the claimed ranges through routine experimentation. Too little of an amount of alcohol would not lead to the diester of the terephthalic acid. Too little of temperature, pressure and time would not allow for
a reaction to take place.
MPEP 2144.05 II. A. and B. “[W]here the general conditions of a claim are
disclosed in the prior art, it is not inventive to discover the optimum or workable ranges
by routine experimentation.” In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA
1955).
Concerning claims 5, the liquid composition is arrived at by the ordinary artisan due to the methods of the prior art being substantially identical to the methods of the current invention. Substantially identical methods yield substantially identical products. See MPEP 2112.01 I. In re Best, 562 F.2d 1252, 1255, 195 USPQ 430, 433 (CCPA 1977). "When the PTO shows a sound basis for believing that the products of the applicant and the prior art are the same, the applicant has the burden of showing that
they are not." In re Spada, 911 F.2d 705, 709, 15 USPQ2d 1655, 1658 (Fed. Cir. 1990).
The methods of the prior art and those of the instant invention both perform
alcoholysis of PET with an alcohol of 4 or more carbons. Due to methods of the prior art and the current invention being substantially identical, the products would have been substantially identical.
Concerning claim 6-7, the discharging is being interpreted as a distillation
discharge. See page 7 of the specification. Cruz-Gomez et al. teach distillation of the mother liquor to generate alcohol and glycol. The ordinary artisan combining the teachings of Cruz-Gomez et al. and Sun et al. would have arrived at the discharging of the unreacted alcohol and/or ethylene glycol via distillation with a reasonable expectation of success. The reason being both Cruz-Gomez et al. and Sun et al. teach distillation to remove the alcohol and glycol.
Concerning claim 7, recovering ethylene glycol by distillation is taught by both Cruz-Gomez et al. and Sun et al. Due to both Cruz-Gomez et al. and Sun et al. teaching substantially identical methods of distillation, the product of the distillation would have been substantially identical. Thus, the recovery rate of 65% or more would have been
achieved by the ordinary artisan.
Concerning claims 8-9, MPEP 2144.05 I.: “In the case where the claimed ranges
“overlap or lie inside ranges disclosed by the prior art” a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976).”
Concerning claims 10 and 11, purification is taught by both Cruz-Gomez et al.
and Sun et al. Both at least teach filtration. Sun et al. teach activated carbon and the
use of 20 grams of activated carbon.
To arrive at the 0.1 to 20% by weight of the total weight of the liquid composition
of the activated carbon, the ordinary artisan knowing the composition is to be purified by activated carbon would have started with the 20 grams taught by Sun et al. and would have found the claimed ranges via routine experimentation. Too little and the composition would not be purified. Too much, the law of diminishing returns.
MPEP 2144.05 II. A. and B. “[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation.” In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955).
Concerning claim 12, MPEP 2144.05 I.: “In the case where the claimed ranges
“overlap or lie inside ranges disclosed by the prior art” a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976).”
Concerning claim 12 and the time of the reaction, the ordinary artisan knowing a
hydrolysis reaction was to take place at the claimed temperatures would have allowed enough time for the reaction to take place and would have found the workable ranges of time via routine experimentation. MPEP 2144.05 II. A. and B. “[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation.” In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955).”
Concerning claim 13 and the weight ratios of liquid composition to water, at least two moles of water to the DAT would be required. Starting from that point the ordinary artisan would have experimented with different amounts of water and DAT to arrive at the current ratios. MPEP 2144.05 II. A. and B. “[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation.” In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955).”
Concerning new claim 21 and the range of carbons, MPEP 2144.05 I.: “In the case where the claimed ranges “overlap or lie inside ranges disclosed by the prior art” a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976).”
Claim(s) 14-15 is/are rejected under 35 U.S.C. 103 as being unpatentable
over Cruz-Gomez et al. (US Patent 5,948,934, Patent date 09-1999), Sun et al. (KR20200046198, Published 05-2020. Machine translation attached) and Toida et al. (USPGPub 2010/0298524) as evidence by Pham et al. (Low-energy catalytic methanolysis of poly(ethyleneterephthalate), Green Chemistry, 23, pp. 511-525, Published 2021) as applied to claims 1, 3-13 and 21 and in further view of Sim et al. (Hydrolysis of Dimethyl Terephthalate for the Production of Terephthalic Acid, J. Chem. Engineering of Japan, Volume 39 Issue 3, pp. 327-333, Published 2006). The modifications to this rejection were necessitated by amendment.
Scope of the Prior Art
The combinational teachings Cruz-Gomez et al. and Sun et al. are in the above 103 rejection and are incorporated by reference.
Ascertaining the Difference
Cruz-Gomez et al., Sun et al. and/or Toida et al. do not teach the use of a hydrolysis catalyst nor the amounts as in claims 14 and 15.
Secondary Reference
Sim et al. teach the hydrolysis of DMT to TPA using a Zn acetate catalyst was increased by 20% (Figure 9, p. 327 right column).
Sim et al. teach overlapping subject matter compared to Cruz-Gomez et al. For
example, Sim et al. teach hydrolysis of DMT to TPA. The above teachings render Sim et al. analogous art to the invention.
Obviousness
It would have been prima facie obvious for an ordinary artisan before the
effective filing date of the claimed invention to have utilized the Zn acetate catalyst in the hydrolysis reactions arrived at by the ordinary artisan. The ordinary artisan would have done so with a reasonable expectation of success because Sim et al. teach the catalyst promotes the hydrolysis reaction by 20%. The ordinary artisan would have looked to Sim et al. because Sim et al. and Cruz-Gomez et al. teach overlapping subject matter, the hydrolysis of DMT to prepare TPA.
Concerning the ppm of the catalyst to the liquid composition, Sim et al. teach the catalyst concentrations (Figure 9, p. 331). Figure 9 shows a direct relationship between catalyst concentration and yield. The ordinary artisan armed with this knowledge would have arrived at the claimed concentrations via routine experimentation. MPEP 2144.05 II. A. and B. “[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation.” In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955).”
Newly Applied Rejections
Claim(s) 20 is/are rejected under 35 U.S.C. 103 as being unpatentable
over Cruz-Gomez et al. (US Patent 5,948,934, Patent date 09-1999), Sun et al. (KR20200046198, Published 05-2020. Machine translation attached) and Toida et al. (USPGPub 2010/0298524) as evidence by Pham et al. (Low-energy catalytic methanolysis of poly(ethyleneterephthalate), Green Chemistry, 23, pp. 511-525, Published 2021) as applied to claims 1, 3-13 and 21 and in further view of Pingping et al. (CN101302158, Published 2006. All references to Pingping et al. are made to an attached translation). This rejection were necessitated by amendment.
Scope of the Prior Art
The combinational teachings Cruz-Gomez et al., Sun et al. and Toida et al. are in the above 103 rejections and are incorporated by reference.
Ascertain the Differences
Cruz-Gomez et al., Sun et al. and/or Toida et al. do not teach the discharging the unreacted alcohol and ethylene glycol in real-time during the alcoholysis reaction.
Secondary References
Pingping et al. teach the following. “(2) The ethylene glycol generated during the reaction process is distilled off along with 2-ethylhexanol. The mixed steam is condensed and refluxed, and the ethylene glycol is removed and recovered by a water scrubber. The 2-ethylhexanol in the condensate after removing the ethylene glycol is returned to the reactor to continue participating in the reaction” (claim 2).
Concerning step (1) of claim 1, Pingping et al. teach “(1) The washed and crushed waste polyester and 2-ethylhexanol are added to the reactor. The molar ratio of waste polyester to 2-ethylhexanol is 1:3-1:20. The mixture is stirred and heated to 170'C-230'C. A catalyst is added to carry out the degradation reaction” (claim 1).
Concerning the end product of the above teachings, Pingping et al. teach a filtrate of DOTP (claim 3). DOTP is the compound of formula 1 wherein R1 is 8. Filtrate implies a liquid and a previous liquid with other substances (current “liquid composition”) (See claim 3 of Pingping et al.).
Additionally, Pingping et al. teach “The reaction described in this invention is a reversible reaction. In order to facilitate the forward reaction, it is necessary to continuously remove the generated ethylene glycol from the reaction system, thereby disrupting the ester exchange reaction equilibrium. This invention adopts the method of adding excess 2-ethylhexanol, which utilizes the rapid formation of an azeotrope between ethylene glycol and 2-ethylhexanol. The reflux liquid is washed with water to remove ethylene glycol from the reaction system, reducing the reaction time. Therefore, the process flow of this invention is short and the production cost is low” (page 5, top).
Obviousness
It would have been prima facie obvious for an ordinary artisan before the effective filing date of the claimed invention to have discharged the unreacted alcohol and the ethylene glycol in real-time, during the alcoholysis reaction arrived at by the ordinary artisan. The ordinary artisan would have done so to satisfy a source for the alcohol to continue participating in the reaction and to facilitate the forward reaction. Upon doing so the ordinary artisan would have arrived at the claimed invention.
A reasonable expectation of success from the fact that Pingping et al. teach ethylene glycol generated during the reaction process is distilled off along with 2-ethylhexanol and the 2-ethylhexanol after removing the ethylene glycol is returned to the reactor.
The ordinary artisan would have looked to Pingping et al. due to the overlapping
subject matter with regards to the prior art, which includes alcoholysis of waste PET to generate a compound of Formula 1. These teachings of Pingping et al. are also deemed analogous art to the invention, the invention also encompasses the alcoholysis of waste PET.
Newly Applied Double Patenting Rejections
The newly applied nonstatutory double patenting rejections were necessitated by the filing date of the claims of the reference applications after the mailing of the most recent office action a non-final on 01/28/2026. The claims of the reference applications were filed after the mailing date of the non-final on 01/28/2026.
Current case 18/727,107 Non-final mailed 01/28/2026.
19/605,056 claims filed 07/09/2026
19/610,243 claims filed 07/29/2026
19/610,252 claims filed 07/29/2026
19/611,723 claims filed 08/03/2026
19/616,825 claims filed 08/20/2026
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claims 1, 3-15 and 20-21 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-17 of copending Application No. 19/605,056 (‘056) filed 07/09/2026 in view of Cruz-Gomez et al. (US Patent 5,948,934, Patent date 09-1999), Sun et al. (KR20200046198, Published 05-2020. Machine translation attached) and Toida et al. (USPGPub 2010/0298524), Sim et al. (Hydrolysis of Dimethyl Terephthalate for the Production of Terephthalic Acid, J. Chem. Engineering of Japan, Volume 39 Issue 3, pp. 327-333, Published 2006), Pingping et al. (CN101302158, Published 2006. All references to Pingping et al. are made to an attached translation), and as evidence by Pham et al. (Low-energy catalytic methanolysis of poly(ethyleneterephthalate), Green Chemistry, 23, pp. 511-525, Published 2021) and Ashenhurst (Master Organic Chemistry, pp. 1-33, Published 03-2021).
Although the conflicting claims are not identical, they are not patentably distinct
from each other because the instantly claimed subject matter embraces or is embraced
by the patented subject matter. For example, ‘056 claims the following.
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‘056 does not claim 1 bar to 28 bar nor the remainder of the ranges of the number of carbon.
However, these limitations and all limitations in the current claims were met with
the prior art in the above 103 rejections. The combinational teachings of Cruz-Gomez et al., and/or Sun et al., and/or Toida et al., and/or Sim et al. and/or, and/or Pingping et al. are in the above 103 rejections and are incorporated by reference.
Consequently, the ordinary artisan would have recognized the obvious variation
of the instantly claimed subject matter over the copending subject matter.
This is a provisional nonstatutory double patenting rejection.
Claims 1, 3-15 and 20-21 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-17 of copending Application No. 19/610,243 (‘243) filed 07/29/2026 in view of Cruz-Gomez et al. (US Patent 5,948,934, Patent date 09-1999), Sun et al. (KR20200046198, Published 05-2020. Machine translation attached) and Toida et al. (USPGPub 2010/0298524), Sim et al. (Hydrolysis of Dimethyl Terephthalate for the Production of Terephthalic Acid, J. Chem. Engineering of Japan, Volume 39 Issue 3, pp. 327-333, Published 2006), Pingping et al. (CN101302158, Published 2006. All references to Pingping et al. are made to an attached translation), and as evidence by Pham et al. (Low-energy catalytic methanolysis of poly(ethyleneterephthalate), Green Chemistry, 23, pp. 511-525, Published 2021) and Ashenhurst (Master Organic Chemistry, pp. 1-33, Published 03-2021).
Although the conflicting claims are not identical, they are not patentably distinct
from each other because the instantly claimed subject matter embraces or is embraced
by the patented subject matter. For example, ‘243 claims the following.
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‘243 does not claim 1 bar to 28 bar nor the remainder of the ranges of the number of carbon.
However, these limitations and all limitations in the current claims were met with the prior art in the above 103 rejections. The combinational teachings of Cruz-Gomez et al., and/or Sun et al., and/or Toida et al., and/or Sim et al. and/or, and/or Pingping et al. are in the above 103 rejections and are incorporated by reference.
Consequently, the ordinary artisan would have recognized the obvious variation
of the instantly claimed subject matter over the copending subject matter.
This is a provisional nonstatutory double patenting rejection.
Claims 1, 3-15 and 20-21 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-17 of copending Application No. 19/610,252 (‘252) filed 07/29/2026 in view of Cruz-Gomez et al. (US Patent 5,948,934, Patent date 09-1999), Sun et al. (KR20200046198, Published 05-2020. Machine translation attached) and Toida et al. (USPGPub 2010/0298524), Sim et al. (Hydrolysis of Dimethyl Terephthalate for the Production of Terephthalic Acid, J. Chem. Engineering of Japan, Volume 39 Issue 3, pp. 327-333, Published 2006), Pingping et al. (CN101302158, Published 2006. All references to Pingping et al. are made to an attached translation), and as evidence by Pham et al. (Low-energy catalytic methanolysis of poly(ethyleneterephthalate), Green Chemistry, 23, pp. 511-525, Published 2021) and Ashenhurst (Master Organic Chemistry, pp. 1-33, Published 03-2021).
Although the conflicting claims are not identical, they are not patentably distinct
from each other because the instantly claimed subject matter embraces or is embraced
by the patented subject matter. For example, ‘252 claims the following.
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‘252 does not claim 1 bar to 28 bar nor the remainder of the ranges of the number of carbon.
However, these limitations and all limitations in the current claims were met with the prior art in the above 103 rejections. The combinational teachings of Cruz-Gomez et al., and/or Sun et al., and/or Toida et al., and/or Sim et al. and/or, and/or Pingping et al. are in the above 103 rejections and are incorporated by reference.
Consequently, the ordinary artisan would have recognized the obvious variation
of the instantly claimed subject matter over the copending subject matter.
This is a provisional nonstatutory double patenting rejection.
Claims 1, 3-15 and 20-21 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-17 of copending Application No. 19/611,723 (‘723) filed 08/03/2026 in view of Cruz-Gomez et al. (US Patent 5,948,934, Patent date 09-1999), Sun et al. (KR20200046198, Published 05-2020. Machine translation attached) and Toida et al. (USPGPub 2010/0298524), Sim et al. (Hydrolysis of Dimethyl Terephthalate for the Production of Terephthalic Acid, J. Chem. Engineering of Japan, Volume 39 Issue 3, pp. 327-333, Published 2006), Pingping et al. (CN101302158, Published 2006. All references to Pingping et al. are made to an attached translation), and as evidence by Pham et al. (Low-energy catalytic methanolysis of poly(ethyleneterephthalate), Green Chemistry, 23, pp. 511-525, Published 2021) and Ashenhurst (Master Organic Chemistry, pp. 1-33, Published 03-2021).
Although the conflicting claims are not identical, they are not patentably distinct
from each other because the instantly claimed subject matter embraces or is embraced
by the patented subject matter. For example, ‘723 claims the following.
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‘723 does not claim 1 bar to 28 bar nor the remainder of the ranges of the number of carbon.
However, these limitations and all limitations in the current claims were met with the prior art in the above 103 rejections. The combinational teachings of Cruz-Gomez et al., and/or Sun et al., and/or Toida et al., and/or Sim et al. and/or, and/or Pingping et al. are in the above 103 rejections and are incorporated by reference.
Consequently, the ordinary artisan would have recognized the obvious variation
of the instantly claimed subject matter over the copending subject matter.
This is a provisional nonstatutory double patenting rejection.
Claims 1, 3-15 and 20-21 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-17 of copending Application No. 19/616,825 (‘825) filed 08/20/2026 in view of Cruz-Gomez et al. (US Patent 5,948,934, Patent date 09-1999), Sun et al. (KR20200046198, Published 05-2020. Machine translation attached) and Toida et al. (USPGPub 2010/0298524), Sim et al. (Hydrolysis of Dimethyl Terephthalate for the Production of Terephthalic Acid, J. Chem. Engineering of Japan, Volume 39 Issue 3, pp. 327-333, Published 2006), Pingping et al. (CN101302158, Published 2006. All references to Pingping et al. are made to an attached translation), and as evidence by Pham et al. (Low-energy catalytic methanolysis of poly(ethyleneterephthalate), Green Chemistry, 23, pp. 511-525, Published 2021) and Ashenhurst (Master Organic Chemistry, pp. 1-33, Published 03-2021).
Although the conflicting claims are not identical, they are not patentably distinct
from each other because the instantly claimed subject matter embraces or is embraced
by the patented subject matter. For example, ‘825 claims the following.
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‘825 does not claim 1 bar to 28 bar nor the remainder of the ranges of the
number of carbon.
However, these limitations and all limitations in the current claims were met with the prior art in the above 103 rejections. The combinational teachings of Cruz-Gomez et al., and/or Sun et al., and/or Toida et al., and/or Sim et al. and/or, and/or Pingping et al. are in the above 103 rejections and are incorporated by reference.
Consequently, the ordinary artisan would have recognized the obvious variation
of the instantly claimed subject matter over the copending subject matter.
This is a provisional nonstatutory double patenting rejection.
Conclusion
THIS ACTION IS MADE FINAL. 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.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to BLAINE G DOLETSKI whose telephone number is (571)272-2766. The examiner can normally be reached M-F 7-4 EST.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Scarlett Goon can be reached at (571)270-5241. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/B.G.D/ Examiner, Art Unit 1692 /Andrew D Kosar/Supervisory Patent Examiner, Art Unit 1625
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