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 .
Response to Arguments
Applicant's arguments filed 1/15/2026 have been fully considered but they are not persuasive.
Specifically, the Applicant argues that Ke discloses an alcoholysis process for preparing a polyester powder coating for recycled materials. The Applicant argues that Ke uses crushed polyester waste neopentyl glycol and a catalyst to create a yellow paste that is added to a reaction vessel and heated where terephthalic acid and a catalyst is added and polycondensation occurs to obtain a low molecular weight resin with narrow molecular weight distribution.
The Applicant argues that Ke has different starting materials, depolymerization and polymerization processes, catalysts and desired end products are different than those in the claimed invention.
The Applicant additionally argues that Ke teaches away from the use of glycolysis ethylene glycol in the method. Specifically that the results of adding ethylene glycol are complex and include many oligomers. Additionally the Applicant argues that this process requires harsh conditions and high temperatures and pressures and a corrosive acid base solution.
The Examiner notes that Seeger also addresses that ethylene glycol/terephthalic acid waste form structures that lead to issue with clogging pipes and disruption of transport (Pages 1 and 2). Seeger points out the proposed method reduces clogging and results in high quality material with good transportability (Page 2).
Additionally Ke teaches the polyester waste mixture is heated to 190-210 C (Page 2), which is considerably higher than the “high temperatures” of Seeger at 80-150C.
This argument incentivizes the combination of Ke and Seeger as Seeger acknowledges and points to a solution for the structures that can form with ethylene glycol terephthalic acid waste.
The Examiner acknowledges Ke does not teach the limitations of claim 1 only the incorporation of step C. The inclusion of Ke and Seeger in combination teaches the limitations of claim 1 where Seeger is an improvement upon the teachings of Ke. The apparent reason to combine Ke and Seeger is the advantage Seeger provides to the teachings of Ke.
The Applicant argues that the present invention does not require the “pretreatment of waste” While Seeger does require the pretreatment of waste. The Examiner notes that Seeger’s definition of pretreatment is a mixture of the ethylene glycol terephthalic acid with a polymer waste which is what is described in claim 1.
The Applicant argues there is no likelihood of success of the combination of Seeger Web teaches a very commonly used polymer that contributes significantly to polymer waste. It would have been obvious that the generalized “polyester waste” referred to in Seeger would have been PET. There is a high likelihood of success of the polyester waste being PET because if the methods taught in Seeger would not function with the most common and most abundant form of polyester waste it is unlikely Seeger would describe the method as functioning with the incorporation of “polyester waste.”
Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claims 1, 6-7, 10, and 14-15 are rejected under 35 U.S.C. 103 as being unpatentable over Ke CN 106065068 A in view of Seeger DD 258240 A1, Webb, H. et al., (Plastic Degradation and Its Environmental Implications with Special Reference to Poly(ethylene terephthalate) Polymers, 2013, 5, 1-18), and of Ma CN110684184A.
Regarding claim 1, 7, 10, and 15, Ke teaches a process for recycling polyester polymers where a pulverized polyester is mixed with a catalyst and neopentyl glycol (Page 2). While this reads on the claimed step (c), Ke is silent on the first step of the claimed process where the polyester is mixed with ethylene glycol and terephthalic acid.
Seeger teaches that in some polyester recycling processes, polyester waste is added directly to monomer compositions without pretreatment (Page 1 Lines 26-30). However, Seeger also teaches that structures form in terephthalic acid/ethylene glycol pastes which lead to disruptions in the transport of the pastes, to an irreversible loss of fluidity and to clogging of the pipes (Page 1 Lines 31-36). Then, when polyester waste is added to the monomer mixture, the storage of the waste leads to an increase in structure formation and thus to a further exacerbation of the transport problems (Page 1 Lines 31-36).
Seeger teaches that in order to improve flowability and transport the polyester can be pretreated with ethylene glycol and terephthalic acid at temperatures from 80-150C prior to esterification and polycondensation (Page 2 Lines 40-51). While both Ke and Seeger are silent on the type of recycled polyester used, Webb teaches that PET is a desirable material for a wide range of applications and a significant component of worldwide plastic consumption (Webb, Page 4). Web also teaches that PET comprises 6.5% of European plastic demand—an excess of over 3,000 tons and more than 50% of synthetic fibers produced around the world consist of PET, and global consumption of PET has been reported to exceed $17 billion per year (Page 4). It would have been obvious to one of ordinary skill in the art at the time of filing to use PET as the waste polyester of Ke in view of Seeger as it is well known in the art as a commonly used plastic that contributes significantly to plastic waste. This reads on the claimed (a). It would have been obvious to one of ordinary skill in the art at the time of filing to combine the teachings of Ke and Seeger for the improvement of increased flowability to the monomer mixture and polyester that Seeger teaches for the process of Ke. The combination of these references necessarily reads on the claimed (b).
Ke teaches that the reaction is heated to 190-210C (Page 2). This reads on the claimed (d).
The limitations of claim (f) state that the esterification product is “further reacted” additional glycols are “optionally included” and this occurs “optionally in the second reaction zone.” Therefore because the reaction of Ke described above that reads on claim (d) where the reaction occurs from 190-210C falls within the claimed range of “at least 200C,” this also reads on the limitations of the claimed (f).
Ke also teaches that the next step is cooling and transferring the composition to a reaction vessel where the polycondensation reaction occurs (Page 2). This reads on the claimed (g) and (h).
Ke is silent on the esterification catalyst comprising Mn, Ti, Zn, Co, Ge or Al. However, Ke teaches that the any modifications, equivalent substitutions, improvements, etc. made within the spirit and scope of the present invention are intended to be included within the scope of the present invention (Page 6). Ma teaches a modified polyester “chip” (or powder) that is has stable quality, and color transparency (Abstract). Ma teaches that the esterification reaction to form the polyester can occur in the presence of the catalyst cobalt acetate (Page 2). Cobalt acetate is well known in the art as an esterification catalyst. It would have been obvious to one of ordinary skill in the art at the time of filing to use cobalt acetate as the catalyst of Ke because it is recognized in the art as an esterification catalyst. It is prima facie obvious to substitute equivalents where the equivalence is recognized by the prior art. See MPEP 2144.06.
Ke teaches the polycondensation catalyst is monobutyltin oxide (Page 2). This reads on the claimed catalyst comprising tin.
Ke in view of Seeger and Webb teaches the composition comprising neopentyl glycol and recycled polyester (PET). Ke is silent on the resulting amounts of neopentyl glycol and ethylene glycol in the composition. Ke is also silent on diethylene glycol being present in the resulting composition.
Ma teaches a modified polyester “chip” (or powder) that is has stable quality, and color transparency (Abstract). Ma teaches that the polyester comprises terephthalic acid, neopentyl glycol, diethylene glycol, and ethylene glycol (Claim 1).
Ma also teaches that simultaneous addition of both NPG and DEG lead to better performance and reduced cost relative to PETG modified only with NPG (Page 2). It would have been obvious to one of ordinary skill in the art at the time of filing to modify the teachings of Ke in view of Seeger and Webb to include a polymer that has both NPG and DEG as taught in Ma for the resulting advantage of a better performing polymer.
Ma teaches that the molar ratio of terephthalic acid, neopentyl glycol, diethylene glycol and ethylene glycol is 1: (0.1-0.5): (0.05-0.1): (0.6-0.8) (Claim 1). This reads on the claimed 10% neopentyl glycol, 10 mol% diethylene glycol and 80% ethylene glycol. This reads on the claimed “wherein the polyester comprises 75 to 93 mol% of ethylene glycol and 5-15 mol% of neopentyl glycol, and 2-10% diethylene glycol based on the total diol residues in the polyester.” It would have been obvious to one of ordinary skill in the art at the time of filing for the polyester powder composition of Ke in view of Seeger, Web, to have the percentages of Ma for the advantages of the polyester chip of MA specifically, stability and color transparency.
Ke in view of Seeger and Webb teaches the composition comprises a recycled polyester (PET) initially treated with terephthalic acid and ethylene glycol then further modified with terephthalic acid (Ke, Page 2). Therefore this reads on the diacid component being 100% terephthalic acid. This reads on the limitations of claims 7 and 10.
Ke does not teach that the esterification reaction occurs at above 240C. However, Ke in view of Seeger, Webb, and Ma teaches a polyester modified with diol components of neopentyl glycol, diethylene glycol, and ethylene glycol in the presence of a cobalt catalyst. This combination of monomers and catalyst requires a reaction temperature of 255-265C (Page 3). It would have been obvious to one of ordinary skill in the art the combine the teachings of Ke in view of Seeger, Webb and Ma to arrive at the reaction temperature of 255-265 because Ma shows that this temperature range is shown to be suitable for this combination of monomers and this catalyst.
Ma also teaches a second esterification reaction that occurs at 265-275C (Page 3) . It would have been obvious to one of ordinary skill in the art at the time of filing to use this temperature range as the temperature range of step (f) because it is shown to be a reasonable temperature range for this combination of monomers and catalyst.
Regarding claim 6, Ke in view of Seeger and Webb is silent on the inherent viscosity of the polyester. Nevertheless, products of identical chemical compositions cannot have mutually exclusive properties. Where the claimed and prior art products are identical or substantially identical in structure or composition, a prima facie case of obviousness has been established. See MPEP 2112.01. The resulting polyester as described above will therefore necessarily possess the claimed inherent viscosity.
Regarding claim 14, Seeger teaches a suspension of ethylene glycol and up to 50% polyester waste (Page 2, Lines 44-45), and combining ethylene glycol and TPA in a molar ratio of 1:1.5 (Page 2, Line 63-65). This equates to a weight ratio of ~4:1 TPA:EG. When EG and polyester waste each make up 50% of the suspension, they’re at a 1:1 weight ratio. This means TPA and polyester are combined at a weight ratio of up 4:1 or higher. In other words, recycled polyester is present in amounts of up to 25 wt% based on the amount of TPA suggested by Seeger.
Claims 8 and 9 are rejected under 35 U.S.C. 103 as being unpatentable over Ke CN 106065068 A in view of Seeger DD 258240 A1, Webb, H. et al., (Plastic Degradation and Its Environmental Implications with Special Reference to Poly(ethylene terephthalate) Polymers, 2013, 5, 1-18), and Ma CN110684184A in further view of Eastar™ copolyester 6763 Data Sheet, 2012 as evidenced by Forloni US 20190389188 A1 .
Regarding claims 8 and 9, Ke in view of Seeger, Webb, and Ma does not teach the incorporation of cyclohexanedimethanol as the modifying glycol of the composition. However, Eastar 6763 Datasheet teaches a PETG that can be used in a wide variety of applications and has a number of advantageous qualities including: high clarity, toughness, and melt strength (Page 3). This polyester comprises terephthalic acid and a diol component of 33 mole % 1,4-cyclohexane dimethanol and about 67 mole % ethylene glycol (Forloni, Paragraph [0094]). This falls within the claimed ranges of 100% terephthalic acid, 65-75% ethylene glycol and 25-35% cyclohexanediol. It would have been obvious to one of ordinary skill in the art at the time of filing form PETG Eastar 6763 using the method of Ke, Seeger, Web, and Ma because this PETG is for the advantages that this polyester is usable in a variety of applications and has the advantageous qualities of high clarity toughness and melt strength.
Claims 11 are rejected under 35 U.S.C. 103 as being unpatentable over Ke CN 106065068 A in view of Seeger DD 258240 A1 and Webb, H. et al., (Plastic Degradation and Its Environmental Implications with Special Reference to Poly(ethylene terephthalate) Polymers, 2013, 5, 1-18), and Ma CN110684184A in further view of Shelby US 6362306B1.
Regarding claim 11, Ke in view of Seeger, Webb, and Ma does not teach the incorporation of cyclohexanedimethanol as the modifying glycol of the composition. Shelby teaches a polyester which comprises terephthalic acid and diol components comprising: 72 to about 88 mole percent ethylene glycol, about 10 to about 15 mole percent 1,4- cyclohexanedimethanol, and about 2 to about 13 mole percent diethylene glycol (Abstract) . This overlaps with the claimed range of at least about 90 mole% terephthalic acid and about 59 to about 77.5 mole% ethylene glycol, and about 15 to about 28 mole% 1,4-cyclohexanedimethanol (CHDM), and about 7.5 to about 13 mole% diethylene glycol (DEG). This polyester is used to form reactor grade polyesters for heat shrinkable films (Abstract). Shelby also teaches that this polyester has higher handleability than other PETG polyesters (Col. 2 Lines 1-30). It would have been obvious to one of ordinary skill in the art at the time of filing form the polyester with the composition of Shelby using the method of Ke, Seeger, Web, and Ma because this polyester has the advantage of being commercially viable in other fields including heat shrinkable applications and has better handleability than other PETG polyesters.
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 LILY K SLOAN whose telephone number is (703)756-5875. The examiner can normally be reached Monday-Friday 9:00-5:30 ET.
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/LILY K SLOAN/Examiner, Art Unit 1762
/ROBERT S JONES JR/Supervisory Patent Examiner, Art Unit 1762
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