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 Amendment
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Any rejections and/or objections made in the previous Office action and not repeated below are hereby withdrawn.
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a).
Claim Rejections - 35 USC § 112
The following is a quotation of the first paragraph of 35 U.S.C. 112(a):
(a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.
The following is a quotation of the first paragraph of pre-AIA 35 U.S.C. 112:
The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor of carrying out his invention.
Claims 7-11 and 13-16 are rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, as failing to comply with the written description requirement. The claim(s) contains subject matter which was not described in the specification in such a way as to reasonably convey to one skilled in the relevant art that the inventor or a joint inventor, or for applications subject to pre-AIA 35 U.S.C. 112, the inventor(s), at the time the application was filed, had possession of the claimed invention.
Claim 7 has been amended to recite the initial copolymer is synthesized from a monomer composition containing terephthalic acid and isophthalic acid. Written support is not found for a copolymer feedstock obtained from both terephthalic acid and isophthalic acid. Rather, support is only found for copolymer synthesized from at least one monomer containing terephthalic acid. Accordingly, claim 7 fails to comply with the written description requirement.
As claims 8-11 and 13-16 depend from claim 7, they are rejected for the same issue discussed above.
Claim Rejections - 35 USC § 103
Claim(s) 7, 8, 10, 11, and 13-16 is/are rejected under 35 U.S.C. 103 as being unpatentable over England (U.S. Pat. No. 3,544,622) in view of Lee (U.S. Pat. No. 6,013,835) and Essaddam (US 2017/0008826 A1).
Regarding Claims 7, 8, 10, and 14, England teaches methods for preparing monomers from polyethylene terephthalate comprising subjecting PET to depolymerization in the presence of ethylene glycol, removing ethylene glycol component, and recovering terephthalic acid monomer (Abstract; Examples). With respect to PET being synthesized from terephthalic acid and isophthalic acid, Essaddam teaches it was known in the art depolymerization of waste PET to terephthalic acid results in various impurities such as isophthalic acid (¶ 84), thus implying waste commercial PETs commonly contain isophthalic acid residues. It would have been obvious to one of ordinary skill in the art to apply depolymerization protocols such as those taught by England to such waste substrates, thereby predictably affording recovered terephthalic acid for re-use in accordance with the teachings of England. England differs from the subject matter claimed in that further purification of crude terephthalic acid via recrystallization is not performed.
Essaddam teaches it was known in the art depolymerization of waste PET to terephthalic acid results in various impurities such as isophthalic acid, 4-formylbenzoic acid, and 4-methylbenzoic acid (¶ 4-17, 84). Lee teaches it was known recrystallization can be used to purify terephthalic acid to remove impurities such as toluic acid and carboxybenzaldehyde (Abstract; Col. 2, Lines 12-59; Tables 1-8). It would have been obvious to one of ordinary skill in the art to apply the recrystallization procedure of Lee toward the crude terephthalic acid of England because doing so would provide terephthalic acid of high purity as taught by Lee.
Lee teaches embodiments where crude terephthalic acid is dissolved in crystallization solvent such as NMP or DMAC at high temperature and cooled to recrystallize out terephthalic acid (Col. 14, Line 42 to Col. 15, Line 28). Lee teaches embodiments where dissolution/saturation temperatures occur within the claimed range, such as 60 degrees C or 110 degrees C (Tables 1 and 2). Lee teaches suitable crystallization temperatures range widely from about 5 to about 50 degrees (Claim 3). Lee teaches embodiments where the obtained crystallized terephthalic acid is passed through a wash column and counter-current water is added to remove crystallization solvent, after which the crystals are soaked in water at temperatures of about 150-250 degrees C and then filtered (Col. 10, Lines 35-39; Col. 15, Lines 30-40). The disclosed temperature ranges overlap the ranges 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 Lee suggests the claimed range. A person of ordinary skill would be motivated to use the claimed amount, based on the teachings of Lee. See MPEP 2123.
Regarding Claim 11, Lee teaches embodiments where recrystallization occurs with 31.8 g TA and 248.4 g of solvent (Table 1), equivalent to 7.8 pbw solvent per 1 pbw TA.
Regarding Claims 13 and 15, England teaches depolymerizing PET with sodium hydroxide base in the presence of ethylene glycol solvent, whereby after filtering to remove diol component the resulting disodium terephthalate is neutralized with an acid prior to washing (Example 2). A stoichiometric amount of hydroxide relative to terephthaloyl content in PET is used (Col. 5, Lines 49-52), equivalent to roughly 2 moles of base relative to 1 mole of PET.
Regarding Claim 16, England teaches the resulting terephthalate can be purified via dissolution, treatment with activated carbon adsorbent, and filtration (Col. 4, Lines 35-48).
Claim(s) 9 is/are rejected under 35 U.S.C. 103 as being unpatentable over England (U.S. Pat. No. 3,544,622) in view of Lee (U.S. Pat. No. 6,013,835), Essaddam (US 2017/0008826 A1), and Lee-2 (U.S. Pat. No. 5,840,968).
The discussion regarding England, Lee, and Essaddam within ¶ 10-15 is incorporated herein by reference.
Regarding Claim 9, to the extent Lee does not describe a preferred quantity of water, Lee-2 teaches the solubility of TPA in water increases substantially at high temperatures (Figure 5):
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530
816
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. Thus, the quantity of hot water used with respect to TPA is a known result effective variable, since clearly the more water used at higher temperatures, the more TPA dissolution would occur. See MPEP 2144.05(II). 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 water quantities within the scope of the present claims so as to produce desirable degrees of crystallization solvent removal from TPA while avoiding excessive TPA crystal dissolution.
Claim(s) 7, 8, 10, 11, and 13-16 is/are rejected under 35 U.S.C. 103 as being unpatentable over England (U.S. Pat. No. 3,544,622) in view of Essaddam (US 2017/0008826 A1), Ham (U.S. Pat. No. 2,949,483), and Lee (U.S. Pat. No. 6,013,835).
Regarding Claims 7, 8, 10, and 14, England teaches methods for preparing monomers from polyethylene terephthalate comprising subjecting PET to depolymerization in the presence of ethylene glycol, removing ethylene glycol component, and recovering terephthalic acid monomer (Abstract; Examples). With respect to PET being synthesized from terephthalic acid and isophthalic acid, Essaddam teaches it was known in the art depolymerization of waste PET to terephthalic acid results in various impurities such as isophthalic acid and 4-methylbenzoic acid (¶ 84), thus implying waste commercial PETs commonly contain isophthalic acid residues. It would have been obvious to one of ordinary skill in the art to apply depolymerization protocols such as those taught by England to such waste substrates, thereby predictably affording recovered terephthalic acid for re-use in accordance with the teachings of England. England differs from the subject matter claimed in that further purification of crude terephthalic acid via recrystallization is not performed.
Ham teaches terephthalic acid is capable of being purified via recrystallization in organic solvents such as N-methylpyrrolidone achieves terephthalic in a highly pure state with removal of impurities such as toluic acid (Col. 1, lines 33-55; Col. 2, Lines 13-25). It would have been obvious to one of ordinary skill in the art to recrystallize the crude terephthalic acids of England using the protocols of Ham because doing so would result in highly pure materials as taught by Ham.
Ham teaches dissolving terephthalic acid in hot NMP, after which a NMP-diacid salt is crystallized out at lower temperatures. After which, the salt crystals are filtered, washed with hot boiling water to further purify the salt, regenerate terephthalic acid, and remove NMP (Col. 3, Line 63 to Col. 4, Line 8; Examples). Ham teaches dissolving crude terephthalic acid in NMP at temperatures spanning 50-130 degrees C after which the mixture is cooled to 10-45 degrees C (Col. 3, Lines 70-74). The dissolution temperature is consistent with the range claimed and the cooling temperature overlaps the range 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 Ham suggests the claimed range. A person of ordinary skill would be motivated to use the claimed amount, based on the teachings of Ham. See MPEP 2123.
Ham differs from the subject matter claimed in that NMP-diacid crystals are not washed with water at 200-300 degrees C. Lee also pertains to recrystallization of terephthalic acid with solvents such as NMP (Abstract; Col. 14, Line 42 to Col. 15, Line 28). Lee teaches the obtained crystallized terephthalic acid is passed through a wash column and counter-current water is added to remove crystallization solvent, after which the crystals are soaked in water at temperatures of about 150-250 degrees C and then filtered (Col. 10, Lines 35-39; Col. 15, Lines 30-40). Lee teaches the soaking protocol is advantageous as it eliminates any possible residual NMP solvent trapped in the crystals before the product is subjected to the final filtration/drying (Col. 4, Lines 46-55; Col. 10, Lines 35-38). It would have been obvious to one of ordinary skill in the art to soak the crystals of Ham with water at a temperature of 150-250 degrees C, because doing so would eliminate any possible residual NMP solvent trapped in the crystals before the product is subjected to the final filtration/drying as taught by Lee.
The disclosed temperature range overlaps the range 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 Lee suggests the claimed range. A person of ordinary skill would be motivated to use the claimed amount, based on the teachings of Lee. See MPEP 2123.
Regarding Claim 11, Ham teaches embodiments where 8 pbw of solvent is used relative to 1 pbw crude terephthalic acid (Example 1).
Regarding Claims 13 and 15, England teaches depolymerizing PET with sodium hydroxide base in the presence of ethylene glycol solvent, whereby after filtering to remove diol component the resulting disodium terephthalate is neutralized with an acid prior to washing (Example 2). A stoichiometric amount of hydroxide relative to terephthaloyl content in PET is used (Col. 5, Lines 49-52), equivalent to roughly 2 moles of base relative to 1 mole of PET.
Regarding Claim 16, England teaches the resulting terephthalate can be purified via dissolution, treatment with activated carbon adsorbent, and filtration (Col. 4, Lines 35-48).
Claim(s) 9 is/are rejected under 35 U.S.C. 103 as being unpatentable over England (U.S. Pat. No. 3,544,622) in view of Essaddam (US 2017/0008826 A1), Ham (U.S. Pat. No. 2,949,483), Lee (U.S. Pat. No. 6,013,835), and Lee-2 (U.S. Pat. No. 5,840,968).
The discussion regarding England, Essaddam, Ham, and Lee, within ¶ 20-27 is incorporated herein by reference.
Regarding Claim 9, to the extent Ham/Lee does not describe a preferred quantity of water, Lee-2 teaches the solubility of TPA in water increases substantially at high temperatures (Figure 5):
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530
816
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Greyscale
. Thus, the quantity of hot water used with respect to TPA is a known result effective variable, since clearly the more water used at higher temperatures, the more TPA dissolution would occur. See MPEP 2144.05(II). 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 water quantities within the scope of the present claims so as to produce desirable degrees of crystallization solvent removal from TPA while avoiding excessive TPA crystal dissolution.
Response to Arguments
Applicant's arguments filed 8/3/2026 have been fully considered but they are not persuasive.
Applicant argues Lee teaches away from high temperature water washing a cooling-crystallized product, reasoning the low crystallization temperatures arise from comparative work at Tables 1-2 and Example 1. This is not found persuasive.
The Examiner finds no indication that Tables 1 and 2 constitute comparative work. Rather, Lee expressly teaches they are according to the present invention (Col. 6, Lines 59-67). Lee teaches beneficial aspects of crystallization occur owing to reducing the temperature/pressure of the dissolved solution (Abstract). Thus, the aspect of Example 1 that Lee seeks to draw a comparison is not a difference in temperatures used; rather it is the non-use of reduced pressure occurring during crystallization.
With respect to Ham, Applicant argues Ham cools to 10-45 degrees C rather than 10 degrees or less. This is not found persuasive as the ranges at issue overlap at 10 degrees C.
Applicant further argues Ham washes with water for a different purpose. This is not found persuasive. It is not necessary that the prior art suggest the combination to achieve the same advantage or result discovered by Applicant. See MPEP 2144(IV).
Applicant argues Lee indicates washing with hot water would negatively impact the crystal structure in a protocol such as that of Ham. This is not found persuasive. The Examiner finds no indication within the claims as to what form the final product of the process takes, whether crystals or powders.
Applicant further argues Lee teaches away from Ham’s crystallization conditions. This is not found persuasive as the rejection does not propose modifying Lee to use Ham’s crystallization conditions.
Applicant argues neither Lee nor Ham depolymerize PET. This is not found persuasive as the limitations concerning deriving TPA from PET is met by combination with England. In response to applicant's arguments against the references individually, one cannot show nonobviousness by attacking references individually where the rejections are based on combinations of references. See In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981); In re Merck & Co., 800 F.2d 1091, 231 USPQ 375 (Fed. Cir. 1986).
Conclusion
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to STEPHEN E RIETH whose telephone number is (571)272-6274. The examiner can normally be reached Monday - Friday, 8AM-4PM Mountain Standard Time.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Curtis Mayes can be reached at (571)272-1234. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/STEPHEN E RIETH/Primary Examiner, Art Unit 1759
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