Prosecution Insights
Last updated: April 19, 2026
Application No. 18/257,678

POLYESTER COMPOSITIONS COMPRISING TETRAMETHYL CYCLOBUTANEDIOL AND 1,4-CYCLOHEXANEDIMETHANOL HAVING AN IMPROVED CATALYST SYSTEM COMPRISING TITANIUM AND ZINC

Non-Final OA §103§112§DP
Filed
Jun 15, 2023
Examiner
KAHN, RACHEL
Art Unit
1766
Tech Center
1700 — Chemical & Materials Engineering
Assignee
Eastman Chemical Company
OA Round
1 (Non-Final)
28%
Grant Probability
At Risk
1-2
OA Rounds
3y 9m
To Grant
44%
With Interview

Examiner Intelligence

Grants only 28% of cases
28%
Career Allow Rate
179 granted / 649 resolved
-37.4% vs TC avg
Strong +16% interview lift
Without
With
+15.9%
Interview Lift
resolved cases with interview
Typical timeline
3y 9m
Avg Prosecution
65 currently pending
Career history
714
Total Applications
across all art units

Statute-Specific Performance

§101
0.2%
-39.8% vs TC avg
§103
48.5%
+8.5% vs TC avg
§102
15.5%
-24.5% vs TC avg
§112
23.7%
-16.3% vs TC avg
Black line = Tech Center average estimate • Based on career data from 649 resolved cases

Office Action

§103 §112 §DP
DETAILED ACTION The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA . Claims 1-4, 6, 7, 9-20, 22 and 23 are pending as amended on 6/15/2023. Information Disclosure Statement The information disclosure statement filed 8/22/2023 fails to comply with 37 CFR 1.98(a)(2), which requires a legible copy of each cited foreign patent document; each non-patent literature publication or that portion which caused it to be listed; and all other information or that portion which caused it to be listed. CA 740050 has not been considered because no copy has been provided. The information disclosure statement filed 8/22/2023 further fails to comply with 37 CFR 1.98(a)(3)(i) because it does not include a concise explanation of the relevance, as it is presently understood by the individual designated in 37 CFR 1.56(c) most knowledgeable about the content of the information, of each reference listed that is not in the English language. The NPL references to HANS MEERWEIN and ANN MEERWEIN (see struck through references) have not been considered. Claim Rejections - 35 USC § 112 The following is a quotation of 35 U.S.C. 112(b): (b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention. The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph: The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention. Claims 11 and 22 are 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. Claim 11 recites a ratio of titanium ppm to zinc ppm to polyester mass from 0.50-1:5 to 5:1. It is not clear which numbers correspond to which component within the recited ratio, and therefore the scope of the claim is unclear. The intended interpretation of the range recited in claim 11 is considered too unclear to apply prior art. Note, however, that claim 20 recites a ratio of titanium to zinc that is clear, and prior art has been applied. Claim 22 recites an extent of TMCD incorporation or conversion in the final polyester which is greater than 55 mol%. It is not clear what is meant by the extent of TMCD incorporation or conversion, nor how to calculate the percentage conversion/incorporation. It is not clear whether the recited percentage is based on a total amount of TMCD monomer utilized, or a total amount of glycol monomer utilized, or a total amount of all monomer utilized, or some other total amount. The specification does not provide guidance or insight into the intended interpretation of the claim, and therefore, the scope of the claim is considered too unclear to reject on the basis of prior art. 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. Claim(s) 1-4, 6-7, 9-10, 12-14, 16-20 and 23 is/are rejected under 35 U.S.C. 103 as being unpatentable over Crawford (US 2007/0145211). As to claims 1-4, 18 and 23, Crawford discloses a polyester composition [0017] (which can be formed into articles [0002]) comprising at least one polyester which comprises: A dicarboxylic acid component comprising: 90-100 mol% terephthalic acid residues [0019] (falling within the presently claimed range of 70-100 mol%); 0 to about 10 mol% of aromatic and/or aliphatic dicarboxylic acid residues having up to 20 carbon atoms [0020] (falling within the presently claimed range of 0 to 30 mol%); A glycol component comprising: 1 to less than 90 mol% 2,2,4,4-tetramethyl-1,3-cyclobutanediol (TMCD) residues [0022], encompassing the presently claimed range of 10 to 60 mol% (or 20 to 40 mol% recited in claim 3); 0 to 89 mol% cyclohexanedimethanol (CHDM) residues [0023] encompassing the presently claimed range of 40 to 90 mol% (or 60-80 mol% recited in claim 4); the 1,4 isomer is named in [0296], and is the isomer utilized in examples [0503]; and; Ethylene glycol [0024] (corresponding to the presently recited optional modifying glycol recited in claims 1 and 2); Wherein the total mol% of diacid component is 100 mol% and total mol% of glycol component is 100 mol% [0026]. When forming a polyester comprising terephthalic acid residues and a diol component including TMCD and CHDM residues, as taught by Crawford, It would have been obvious to the person having ordinary skill in the art to have selected any appropriate molar percentages for each of the TMCD and CHDM residues from within the corresponding ranges for each of TMCD and CHDM taught by Crawford, including percentages within the presently claimed ranges, in order to provide a polyester as disclosed by Crawford having a desired impact strength, Tg, inherent viscosity, clarity, color and/or modulus [0008]. Case law has established that a prima facie case of obviousness is established where the claimed ranges overlap the ranges disclosed by the prior art. See MPEP 2144.05. Crawford further teaches that the polyester composition comprises titanium and phosphorus atoms [0026]. Crawford further teaches that the amount of tin atoms can be from 0 to 400 ppm [0218], which overlaps the presently claimed range of less than 30 ppm tin atoms. Crawford teaches that tin catalysts are efficient for incorporation of TMCD into a polyester, but that deleterious color interactions occur when used to prepare polyesters containing ethylene glycol. The b* color value of the polyester is improved by the use of the catalysts in combination with phosphorus compounds [0005, 0307]. Note that while titanium and phosphorus are both disclosed as required components in the polyester composition, tin is named by Crawford as an optional component (see, e.g., [0093]). In view of Crawford’s disclosure, the person having ordinary skill in the art would have been motivated to select any appropriate tin content within Crawford’s disclosed range of 0 to 400 ppm in order to achieve a desired balance between b* color improvement and TMCD incorporation efficiency. It would have been obvious to the person having ordinary skill in the art, therefore, to have formed a polyester composition comprising titanium and phosphorus, as suggested by Crawford, by including tin catalyst in any appropriate amount within a range of 0 to 400 ppm, including within the presently claimed range of less than 30 ppm. Case law has established that a prima facie case of obviousness is established where the claimed ranges overlap the ranges disclosed by the prior art. See MPEP 2144.05. As to the recited zinc atoms residues: Crawford further teaches that in addition to at least one titanium compound and at least one phosphorus compound, the polyester composition optionally comprises a catalyst chosen from a list which includes zinc [0093]. It would have been obvious to the person having ordinary skill in the art to have combined Crawford’s required titanium and phosphorus components together with any appropriate catalyst from those named by Crawford as optional, including zinc, in order to achieve a desired reactivity and polymerization rate throughout the synthesis of the polyester, thereby arriving at a polyester comprising catalyst residues comprising titanium and zinc, as presently recited. As to claim 6, Crawford discloses an inherent viscosity from 0.50 to 1.2 dL/g [0026], which falls within the claimed range. As to claim 7, Crawford names manganese and gallium as optional catalysts [0093]. Crawford nowhere requires manganese or gallium within the composition. It would have been obvious to the person having ordinary skill in the art to prepared a polyester composition as suggested by Crawford by excluding any one or more of the optional catalysts named by Crawford, including manganese and/or gallium, in order to provide a composition suitable for applications wherein residues of such metals are prohibited or not desired. As to claim 9, Crawford discloses a polyester composition wherein the amount of titanium atoms is 1 to 400 ppm [0224], which overlaps the presently claimed range of 20 to 1000 ppm. (See also broader disclosed ranges in [0351]). It would have been obvious to the person having ordinary skill in the art to have selected any appropriate amount of titanium within Crawford’s disclosed range of 1 to 400 ppm in order to achieve a desired catalytic effect on polymerization including an amount within the presently claimed range. Case law has established that a prima facie case of obviousness is established where the claimed ranges overlap the ranges disclosed by the prior art. See MPEP 2144.05. As to claims 10 and 12, Crawford discloses that the catalyst amounts can range from 10 to 250 ppm based on the catalyst metal and based on the weight of the final polymer [0348]. It would have been obvious to the person having ordinary skill in the art to have selected any appropriate amount of zinc and titanium within Crawford’s disclosed range of 10 to 250 ppm in order to achieve a desired catalytic effect on polymerization balanced with minimizing disadvantages associated with using high amounts of catalyst (color, cost, etc…), including an amount of zinc within the range recited in claim 10 and further including amounts of each catalyst corresponding to a total metal concentration within the range recited in claim 12. Case law has established that a prima facie case of obviousness is established where the claimed ranges overlap the ranges disclosed by the prior art. See MPEP 2144.05. As to claims 13 and 14, Crawford names several titanium compounds in [0363], several of which correspond to titanium sources recited in claims 13 and 14. In Crawford’s examples, the titanium source is titanium isopropoxide [0513], which is recited in the present claims. As to claims 16, Crawford discloses an embodiment wherein the molar ratio of cis/trans TMCD is greater than 70 mol% cis and less than 30 mole% trans [0294]. As to claim 17, Crawford discloses a blend as presently recited in [0430-433]. As to claim 19, the methyl content of a polyester composition as suggested by Crawford must at least decrease as the content of TMCD (which contains four methyl groups) decrease. As set forth above, when forming a polyester comprising terephthalic acid residues and a diol component including TMCD and CHDM residues, as taught by Crawford, it would have been obvious to the person having ordinary skill in the art to have selected any appropriate molar percentages for each of the TMCD and CHDM residues from within the corresponding ranges for each of TMCD and CHDM taught by Crawford, including percentages within the presently claimed ranges, and further including corresponding to a methyl group content within the range recited in claim 19, in order to provide a polyester as disclosed by Crawford having a desired impact strength, Tg, inherent viscosity, clarity, color and/or modulus [0008]. Case law has established that a prima facie case of obviousness is established where the claimed ranges overlap the ranges disclosed by the prior art. See MPEP 2144.05. As to claim 20, Crawford discloses an inherent viscosity from 0.50 to 1.2 dL/g [0026], as well as narrower preferred ranges in [0286] which fall within the presently recited range of 0.45 to 0.75 dL/g (such as 0.50 to 0.72 dL/g). Crawford further teaches a b* value ranging from 0 to 5 [0165], which falls within the presently claimed range of less than 6. Crawford further teaches that catalysts include at least one titanium compound, and names zinc as another catalyst that can be used in combination with the at least one titanium compound [0347]. Crawford teaches that catalyst amounts range from 10 to 250 ppm based on the catalyst metal and based on the weight of the final polymer [0348]. Considering that Crawford does not disclose different ranges for different catalysts in [0348], one having ordinary skill in the art would have at least envisaged utilizing equivalent amounts of each type of catalyst when combining different catalysts, corresponding to a ratio of titanium to zinc of 1:1 (a ratio which falls within the presently claimed range of 0.8:3 to 3:1). Claim(s) 15 is/are rejected under 35 U.S.C. 103 as being unpatentable over Crawford (US 2007/0145211) in view of Crawford et al (US 2013/0072628; herein “Crawford-2”). The rejection above over Crawford is incorporated here by reference. As to claim 15, Crawford fails to name a particular zinc containing catalyst. Like Crawford, Crawford-2 discloses a polyester comprising residues of terephthalic acid, TMCD and CHDM [0002]. Crawford-2 similarly teaches zinc catalyst among a list of suitable catalysts [0489], and teaches that the use of this type of catalyst is well known in the art. Crawford-2 names zinc acetate as an example catalyst, and teaches catalyst amounts in ranges which are the same as the ranges taught by Crawford [0492]. When forming a polyester utilizing zinc as suggested by Crawford, the person having ordinary skill in the art would have been motivated to utilize a zinc catalyst known in the art as being effective for forming the type of polyester taught by Crawford in order to ensure sufficient catalytic performance. Considering the substantial similarities regarding the monomers used to form the polyesters in Crawford and Crawford-2, and further considering Crawford-2’s characterization of zinc acetate as an example of a zinc catalyst which is well known for use in the art, one having ordinary skill in the art would have had a reasonable expectation of success in selecting zinc acetate as an effective zinc catalyst for forming a polyester composition as taught by Crawford. It would have been obvious to the person having ordinary skill in the art, therefore, to have combined Crawford’s required titanium and phosphorus components together with any appropriate catalyst from those named by Crawford as optional, including zinc acetate as named by Crawford-2, in order to achieve a desired reactivity and polymerization rate throughout the synthesis of the polyester. Double Patenting 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 1-4, 6, 7, 9-19, 22 and 23 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims of copending Application No. 18/257703 (reference application). Although the claims at issue are not identical, they are not patentably distinct from each other: As to claim 1, copending claim 1 is substantially the same as instant claim 1, except that copending claim 1 recites 40-90 mol% of at least one modifying glycol, while instant claim 1 more narrowly recites 40-90 mol% of CHDM. Dependent copending claim 4 further limits the modifying glycol, including to CHDM, which would meet instant claim 1. Instant claim 2 is met by copending claim 1 for at least the reason that instant claim 2 does not require a modifying glycol. As to instant claims 3 and 4, the corresponding ranges recited in copending claim 1 encompass, and therefore render obvious, the presently claimed ranges. The viscosity range recited in instant claim 6 is recited in copending claim 6. As to instant claim 7, copending claims 7 and 8 recite ranges of manganese and gallium, respectively, which encompass 0 ppm. As to claims 9, 10 and 11, copending claims 9 and 10 recite the same range for zinc atom amount recited in instant claim 10 and the same range for the ratio of titanium to zinc recited in instant claim 11, which meets instant claims 10 and 11, and renders obvious instant claim 9. The range of total catalyst metal atoms recited in instant claim 12 is recited in copending claim 11. The titanium and zinc sources recited in instant claims 13-15 are recited in copending claims 13 and 14. The cis/trans range recited in instant claim 16 is recited in copending claim 15. The recitations of instant claims 17 and 18 are in copending claims 17 and 18. The methyl group range recited in claim 19 is in copending claim 16. The recitations of instant claims 22 and 23 are in copending claims 19 and 20. This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented. Conclusion Any inquiry concerning this communication or earlier communications from the examiner should be directed to RACHEL KAHN whose telephone number is (571)270-7346. The examiner can normally be reached Monday to Friday, 8-5. Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice. If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Randy Gulakowski can be reached at 571-272-1302. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300. Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000. /RACHEL KAHN/ Primary Examiner, Art Unit 1766
Read full office action

Prosecution Timeline

Jun 15, 2023
Application Filed
Mar 02, 2026
Non-Final Rejection — §103, §112, §DP (current)

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Study what changed to get past this examiner. Based on 5 most recent grants.

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Prosecution Projections

1-2
Expected OA Rounds
28%
Grant Probability
44%
With Interview (+15.9%)
3y 9m
Median Time to Grant
Low
PTA Risk
Based on 649 resolved cases by this examiner. Grant probability derived from career allow rate.

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