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Any rejections and/or objections made in the previous Office action and not repeated below are hereby withdrawn.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 Interpretation
The claims indicate various materials are obtained “directly” or “indirectly” from various processes. Per the definition of ¶ 60, a material “directly” derived from a process is construed as having at least one physical component that is traceable back to the referred upon process. For instance, a r-propylene “derived directly” from cracking a recycle content pyrolysis oil composition means the r-propylene contains component(s) that can be traced back to the pyrolysis oil cracking process. In contrast, a material “indirectly” derived from a process is construed as may or may not having any component that is traceable back to the referred upon process. For instance, r-propylene that is purified to the extent that no components are traceable back to the cracking process is “indirectly” derived, as opposed to “directly” derived.
Likewise, the terminology “cracking a recycle content pyrolysis oil composition (r-pyoil) to obtain a recycle content 2,2,4,4-tetramethyl-1,3-cyclobutanediol (r-TMCD)” is not seen to necessarily imply TMCD itself is a product of cracking r-pyoil, but various intermediate steps or entities (e.g. r-propylene) can be present. See ¶ 75 of the specification.
Claim Objections
Claim 4 is objected to because of the following informalities: “the at least one recycle reactant” should be “the at least one recycle polyester reactant”. Appropriate correction is required.
Claim Rejections - 35 USC § 112
Claim 5 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.
The terminology “the dicarboxylic acid component” lacks antecedent basis. Therefore, the intended scope of the claim is unclear.
Claim 5 depends alternatively on independent claim 2, but requires a specified content of “the recycle DMT”. The terminology lacks antecedent basis with respect to claim 2. Therefore, the intended scope of the claim is unclear.
Claim Rejections - 35 USC § 103
Claim(s) 1-3 is/are rejected under 35 U.S.C. 103 as being unpatentable over Treece (US 2013/0029068 A1) in view of Maxwell (US 2013/0184505 A1).
Regarding Claims 1-3, Treece teaches methods of producing polyesters from terephthalic acid derivatives, ethylene glycol, and CHDM (Abstract; Examples). The polyesters can be produced from recycled monomers, such as DMT/CHDM produced via methanolysis of polyethylene terephthalate (¶ 302). Propylene glycol can be used as additional diol (¶ 259). Treece differs from the subject matter claimed in that recycled component prepared from propylene / pyrolysis oil is not described.
Maxwell teaches processes of making chemical feedstocks from biomass / bio-oils from pyrolysis (Abstract; ¶ 79). The oils are cracked to produce propylene, which can used to create materials used in the preparation of polyester resins, such as propylene glycol (¶ 154, 159). It would have been obvious to one of ordinary skill in the art to create polyester-producing materials such as propylene glycol from the propylene / bio-oils of Maxwell because doing so would increase the renewable / non-petroleum content of such polyesters based on the teachings of Maxwell.
Claim(s) 1-12, 19, and 20 is/are rejected under 35 U.S.C. 103 as being unpatentable over Pecorini (US 2013/0041053 A1) in view of Maxwell (US 2013/0184505 A1) and Tullo (“Babies on Board”; C&E News).
Regarding Claims 1-4, Pecorini teaches methods of producing polyesters from materials formed via depolymerization by methanolysis or glycolysis, such as dimethyl terephthalate, terephthalic acid, and/or cyclohexanedimethanol; the CHDM either resulting from depolymerizing the polyester itself or via hydrogenating DMT (Abstract; ¶ 9, 34-35; Examples). Pecorini teaches an example where polyethylene terephthalate is depolymerized under depolymerization conditions to yield dimethyl terephthalate, the dimethyl terephthalate is recovered and a fraction of which is converted to CHDM, and the recycled DMT, CHDM, and TMCD diol (2,2,4,4-tetramethyl-1,3-cyclobutanediol) is polymerized to produced recycled polyester (Abstract; ¶ 51), the TMCD diol construed as polyester reactant.
Pecorini differs from the subject matter claimed in that it is not indicated recycle TMCD is derived from propylene from pyrolysis oils. Maxwell teaches processes of making chemical feedstocks from biomass / bio-oils from pyrolysis (Abstract; ¶ 79). The oils are cracked to produce propylene, which can be used to create materials used in the preparation of polyester resins (¶ 154, 159). Tullo teaches it was known in the art TMCD can be produced from propylene feedstock (Page 20, center column). It would have been obvious to one of ordinary skill in the art to create TMCD of Pecorini using the propylene feedstock of Maxwell because doing so would increase the renewable content of such polyesters in accordance with the teachings of Maxwell (¶ 2).
Regarding Claim 5, Pecorini teaches embodiments where 100 mol% of the acid component is terephthalic acid residues derived from DMT (¶ 52). TMCD can constitute 10-90 mol% of the glycol component (¶ 45), which overlaps 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 Pecorini suggests the claimed range. A person of ordinary skill would be motivated to use the claimed amount, based on the teachings of Pecorini. See MPEP 2123.
Regarding Claims 6-8, Pecorini teaches methods of producing polyesters from materials formed via depolymerization by methanolysis or glycolysis, such as dimethyl terephthalate, terephthalic acid, and/or cyclohexanedimethanol; the CHDM either resulting from depolymerizing the polyester itself or via hydrogenating DMT (Abstract; ¶ 9, 34-35; Examples). Examples are taught where recycled DMT and CHDM is reacted with 2,2,4,4-tetramethyl-1,3-cyclobutanediol (¶ 51). A portion of the recycled diacid can be TPA produced from DMT (¶ 35).
Pecorini differs from the subject matter claimed in that it is not indicated recycle TMCD is derived from cracking pyrolysis oils. Maxwell teaches processes of making chemical feedstocks from biomass / bio-oils from pyrolysis (Abstract; ¶ 79). The oils are cracked to produce propylene, which can used to create materials used in the preparation of polyester resins (¶ 154, 159). Tullo teaches it was known in the art TMCD can be produced from propylene feedstock (Page 20, center column). It would have been obvious to one of ordinary skill in the art to create TMCD of Pecorini using the propylene feedstock of Maxwell because doing so would increase the renewable content of such polyesters in accordance with the teachings of Maxwell (¶ 2).
Regarding Claim 9, Pecorini teaches methods of producing polyesters from materials formed via depolymerization by methanolysis or glycolysis, such as dimethyl terephthalate, terephthalic acid, and/or cyclohexanedimethanol; the CHDM either resulting from depolymerizing the polyester itself or via hydrogenating DMT (Abstract; ¶ 9, 34-35; Examples). Pecorini teaches an example where TMCD is obtained, DMT is obtained from the glycolysis of terephthalate polyester, and TMCD and DMT are fed to a reactor under conditions effective to make a polyester (Abstract; ¶ 51). While DMT is obtained via glycolysis and not methanolysis, Pecorini teaches either methanolysis or glycolysis is suitable (Abstract).
Pecorini differs from the subject matter claimed in that it is not indicated recycle TMCD is derived from cracking pyrolysis oils. Maxwell teaches processes of making chemical feedstocks from biomass / bio-oils from pyrolysis (Abstract; ¶ 79). The oils are cracked to produce propylene, which can used to create materials used in the preparation of polyester resins (¶ 154, 159). Tullo teaches it was known in the art TMCD can be produced from propylene feedstock (Page 20, center column). It would have been obvious to one of ordinary skill in the art to create TMCD of Pecorini using the propylene feedstock of Maxwell because doing so would increase the renewable content of such polyesters in accordance with the teachings of Maxwell (¶ 2).
Regarding Claim 10, Pecorini teaches methods of producing polyesters from materials formed via depolymerization by methanolysis or glycolysis, such as dimethyl terephthalate, terephthalic acid, and/or cyclohexanedimethanol; the CHDM either resulting from depolymerizing the polyester itself or via hydrogenating DMT (Abstract; ¶ 9, 34-35; Examples). Pecorini teaches an example where TMCD is obtained, CHDM is obtained via hydrogenating DMT from the glycolysis of terephthalate polyester, and TMCD, DMT, and CHDM are fed to a reactor under conditions effective to make a polyester (Abstract; ¶ 51). Pecorini teaches either methanolysis or glycolysis is suitable (Abstract).
Pecorini differs from the subject matter claimed in that it is not indicated recycle TMCD is derived from cracking pyrolysis oils. Maxwell teaches processes of making chemical feedstocks from biomass / bio-oils from pyrolysis (Abstract; ¶ 79). The oils are cracked to produce propylene, which can used to create materials used in the preparation of polyester resins (¶ 154, 159). Tullo teaches it was known in the art TMCD can be produced from propylene feedstock (Page 20, center column). It would have been obvious to one of ordinary skill in the art to create TMCD of Pecorini using the propylene feedstock of Maxwell because doing so would increase the renewable content of such polyesters in accordance with the teachings of Maxwell (¶ 2).
Regarding Claim 11, Pecorini teaches methods of producing polyesters from materials formed via depolymerization by methanolysis or glycolysis, such as dimethyl terephthalate, terephthalic acid, and/or cyclohexanedimethanol; the CHDM either resulting from depolymerizing the polyester itself or via hydrogenating DMT (Abstract; ¶ 9, 34-35; Examples). Pecorini teaches an example where TMCD is obtained, CHDM is obtained via hydrogenating DMT from the glycolysis of terephthalate polyester, and TMCD, DMT, and CHDM are fed to a reactor under conditions effective to make a polyester (Abstract; ¶ 51). Pecorini teaches either methanolysis or glycolysis is suitable (Abstract).
Pecorini differs from the subject matter claimed in that it is not indicated recycle TMCD is derived from cracking pyrolysis oils. Maxwell teaches processes of making chemical feedstocks from biomass / bio-oils from pyrolysis (Abstract; ¶ 79). The oils are cracked to produce propylene, which can used to create materials used in the preparation of polyester resins (¶ 154, 159). Tullo teaches it was known in the art TMCD can be produced from propylene feedstock (Page 20, center column). It would have been obvious to one of ordinary skill in the art to create TMCD of Pecorini using the propylene feedstock of Maxwell because doing so would increase the renewable content of such polyesters in accordance with the teachings of Maxwell (¶ 2).
Regarding Claim 12, Pecorini teaches methods of producing polyesters from materials formed via depolymerization by methanolysis or glycolysis, such as dimethyl terephthalate, terephthalic acid, and/or cyclohexanedimethanol; the CHDM either resulting from depolymerizing the polyester itself or via hydrogenating DMT (Abstract; ¶ 9, 34-35; Examples). Pecorini teaches an example where TMCD is obtained, CHDM is obtained via hydrogenating DMT from the glycolysis of terephthalate polyester, and TMCD, DMT, and CHDM are fed to a reactor under conditions effective to make a polyester (Abstract; ¶ 51). Pecorini teaches either methanolysis or glycolysis is suitable (Abstract).
Pecorini differs from the subject matter claimed in that it is not indicated recycle TMCD is derived from cracking pyrolysis oils. Maxwell teaches processes of making chemical feedstocks from biomass / bio-oils from pyrolysis (Abstract; ¶ 79). The oils are cracked to produce propylene, which can used to create materials used in the preparation of polyester resins (¶ 154, 159). Tullo teaches it was known in the art TMCD can be produced from propylene feedstock (Page 20, center column). It would have been obvious to one of ordinary skill in the art to create TMCD of Pecorini using the propylene feedstock of Maxwell because doing so would increase the renewable content of such polyesters in accordance with the teachings of Maxwell (¶ 2).
Regarding Claims 19 and 20, Pecorini teaches methods of producing polyesters from materials formed via depolymerization by methanolysis or glycolysis, such as dimethyl terephthalate, terephthalic acid, and/or cyclohexanedimethanol; the CHDM either resulting from depolymerizing the polyester itself or via hydrogenating DMT (Abstract; ¶ 9, 34-35; Examples). Pecorini teaches an example where polyethylene terephthalate is depolymerized under depolymerization conditions to yield dimethyl terephthalate, the dimethyl terephthalate is recovered and a fraction of which is converted to CHDM, and the recycled DMT, CHDM, and TMCD diol is polymerized to produced recycled polyester (Abstract; ¶ 51). The depolymerization of polyethylene terephthalate into DMT intrinsically produces ethylene glycol. The diacid residues are obtained from recycled residues.
Pecorini differs from the subject matter claimed in that it is not indicated recycle TMCD is derived from cracking pyrolysis oils. Maxwell teaches processes of making chemical feedstocks from biomass / bio-oils from pyrolysis (Abstract; ¶ 79). The oils are cracked to produce propylene, which can used to create materials used in the preparation of polyester resins (¶ 154, 159). Tullo teaches it was known in the art TMCD can be produced from propylene feedstock (Page 20, center column). It would have been obvious to one of ordinary skill in the art to create TMCD of Pecorini using the propylene feedstock of Maxwell because doing so would increase the renewable content of such polyesters in accordance with the teachings of Maxwell (¶ 2).
Double Patenting
The double patenting rejection is withdrawn in view of the filed terminal disclaimer.
Response to Arguments
Applicant's arguments filed 3/20/2026 have been fully considered but they are not persuasive.
Applicant generally argues Maxwell fails to describe cracking r-pyoil to obtain r-propylene or r-TMCD. This is not found persuasive.
Per the specification, a “r-pyoil” is a composition of matter where at least a portion of which is obtained from the pyrolysis of recycled waste (¶ 55). By “recycled waste”, it is meant any type of waste that is reused in a production process rather than disposed, such as biowaste (¶ 121).
Maxwell generally describes the processing of biomass waste into lower olefin feedstocks:
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. The bio-mass waste can be converted to bio-oil via pyrolysis (¶ 79) and thus, the bio-oil of Maxwell is a “r-pyoil” within the scope of the present application. The bio-oil can be cracked to form feedstocks. The cracking process can be used to create products such as lower olefins / propylene (¶ 116-120, 150, 154). Therefore, Maxwell expressly teaches cracking r-pyoil to obtain r-propylene (or to “obtain TMCD” via the combination of references; see the Claim Interpretation section above).
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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