Prosecution Insights
Last updated: April 19, 2026
Application No. 17/906,251

Thermoplastic Polyurethane Compositions Comprising Nitro-Substituted Polyester Diols

Non-Final OA §103
Filed
Sep 13, 2022
Examiner
AMATO, ELIZABETH KATHRYN
Art Unit
1762
Tech Center
1700 — Chemical & Materials Engineering
Assignee
Novoloop, Inc.
OA Round
3 (Non-Final)
82%
Grant Probability
Favorable
3-4
OA Rounds
3y 2m
To Grant
84%
With Interview

Examiner Intelligence

Grants 82% — above average
82%
Career Allow Rate
18 granted / 22 resolved
+16.8% vs TC avg
Minimal +2% lift
Without
With
+2.1%
Interview Lift
resolved cases with interview
Typical timeline
3y 2m
Avg Prosecution
36 currently pending
Career history
58
Total Applications
across all art units

Statute-Specific Performance

§101
1.4%
-38.6% vs TC avg
§103
60.7%
+20.7% vs TC avg
§102
15.9%
-24.1% vs TC avg
§112
19.3%
-20.7% vs TC avg
Black line = Tech Center average estimate • Based on career data from 22 resolved cases

Office Action

§103
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 . Claim Rejections - 35 USC § 103 In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status. 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. Claims 29-33, 41-42, and 46 are rejected under 35 U.S.C. 103 as being unpatentable over Hackl (US 4748195) in view of Yao (US 2019/0322833). All references have been cited in a prior Office Action. Regarding claims 29-33, 41-42, and 46, Hackl teaches polyurethane elastomers prepared at reaction temperature from 60-200°C from a diisocyanate, a polyhydroxy compound such as one or several polyester polyols, and a chain extender, which may be an aliphatic diol including diethylene glycol, in the presence of a catalyst that accelerates the reaction between isocyanate groups and hydroxyl groups, and optional additives, which may be fillers or dyes (col. 7, lines 4-8, 11, 42, 52-54; col. 8, lines 63-67; col. 9, lines 6, 34-36, 50-54; col. 10, lines 7-8). Hackl further teaches that the polyisocyanate may be 4,4'-dicyclohexylmethane diisocyanate, and that a combination of polyester polyols, including several of the non-nitro-containing variety, may be used (col. 7, lines 19-20, 52-54; col. 8, lines 23-35). However, Hackl is silent as to use of nitro-substituted polyester diols. In a similar field of endeavor, Yao teaches recycling polymer into a mixture of nitro-substituted dicarboxylic acids (Fig. 22) that may be reacted with other ingredients at temperatures ranging from 60-200℃ (p. 2, [0030]) in a stirred tank reactor (p. 5, [0093]). Yao suggests using the decomposition products as raw feedstock for new products to avoid adverse environmental consequences (p. 1, [0004]). Hackl recognizes the suitability of dicarboxylic acids for polyester synthesis (col. 8, line 27). Yao’s decomposition products, used as the dicarboxylic acid component in Hackl’s polyester polyol, and reacted with a polyfunctional alcohol like a diol will result in a polyester polyol of the claimed structure (col. 8, lines 23-30 and 40-48). Hackl and Yao do not limit the sequence of addition of the various ingredients, and permit addition of the ingredients in any order, at any temperature within that range. It would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to select the nitro-substituted diacids of Yao for use as the diacid component of Hackl’s polyester polyol to arrive at the claimed invention, and to conduct synthesis with reduced adverse environmental consequences, as suggested by Yao (p. 1, [0003]-[0005]). Claims 34, 44-45, and 48-49 are rejected under 35 U.S.C. 103 as being unpatentable over Hackl in view of Yao, and further in view of Brockway (US 3,692,597). Regarding claim 34, Hackl in view of Yao remains as applied to claim 29 above. However, Hackl is silent as to the amounts of the various ingredients that may be used. In a similar field of endeavor, Brockway teaches a composition having 70-87% by weight ammonium perchlorate and 1-2% by weight copper hexadecachlorophthalocyanine balanced with 11-29% by weight of the reaction product of 1.3 to 2.0 mol polyisocyanate (208.17-320.26 g p-phenylene diisocyanate) with 1 mol polyester (600-3,000 g polyethylene adipate; see col. 4, lines 17-18) and 0.2-0.8 mol curing agent (26.83-107.3 g trimethylolpropane) (claim 24). Brockway's polyester may be nitro-substituted (col. 3, lines 72-73). This results in a composition having a total weight of 2,879-11,820 g, including 0.91-0.93% by weight curing agent (chain extender), 2.7-7.2% by weight polyisocyanate, and 20.8-25.4% by weight polyester in the total composition. However, the instant composition contains solely polymer. Relative to the total amount of polymer (835 to 3428 g) taught by Brockway, the composition contains 3.13-3.2% by weight curing agent/chain extender, 9.34-24.9% by weight polyisocyanate, and 71.8-87.5% by weight polyester. Whether taken relative to the total composition or to the total amount of polymer, at least one of these prior art ranges overlaps the claimed ranges. A prima facie case of obviousness exists where the prior art range overlaps the claimed range. See MPEP 2144.05. It would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to combine the ingredients of Hackl in view of Yao with the amounts specified by Brockway to arrive at the claimed invention, in order to achieve optimal chemical stability over an extended useful temperature range, as taught by Brockway (col. 1, lines 47-48). Regarding claims 44-45, Hackl in view of Yao remains as applied to claim 29 above. However, Hackl and Yao are silent as to use of a crosslinking agent in the composition. In a similar field of endeavor, Brockway further teaches crosslinking the polymer with a polyfunctional hydroxyl, polyhydroxy, curing agent (col. 3, lines 40-42). More specifically, Brockway teaches use of trimethylolpropane to crosslink the composition (claim 24). It would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to combine the ingredients of Hackl in view of Yao with the crosslinking agent of Brockway to arrive at the claimed invention and to produce an easily processable composition, as taught by Brockway (col. 3, lines 47-50). Regarding claims 48-49, Hackl in view of Yao remains as applied to claim 29 above. Brockway further teaches use of additives, including dyes, in amounts ranging from 0.1-2% by weight, and teaches use of no filler (0% by weight) (col. 5, lines 18-25 and 47-55). These ranges overlap the claimed range of less than 20% by weight. A prima facie case of obviousness exists where the prior art range overlaps the claimed range. See MPEP 2144.05. It would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to combine the ingredients of Hackl and Yao with the additive of Brockway to arrive at the claimed invention and to adjust the characteristics of the composition, as suggested by Brockway (col. 5, lines 47-64). Claims 35, 37-39, and 52 are rejected under 35 U.S.C. 103 as being unpatentable over Hackl in view of Yao, and further in view of Slagel (US 5811506 A). Regarding claims 35 and 52, Hackl in view of Yao remains as applied to claim 29 above. However, Hackl and Yao are silent as to molding and curing of the composition. In the same field of endeavor, Slagel teaches post-reaction treatment of casting into molds and curing (col. 8, lines 61-62). The composition may further be pelletized and extruded (col. 7, lines 30-31 It would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to combine the composition of Hackl in view of Yao with the mold treatment of Slagel to arrive at the claimed invention, and to produce extrudable polyurethanes with excellent thermal properties and physical properties, as taught by Slagel (col. 7, lines 59-61). Regarding claims 37-39, Hackl in view of Yao remains as applied to claim 29 above. However, Hackl and Yao are silent as to further modification with aliphatic glycol. In the same field of endeavor, Slagel teaches modifying the polyester diol with additional aliphatic glycol such as ethylene glycol (claim 11). Yao teaches use of nitro-suberic acid as a suitable polyester diacid (Fig. 22). The claimed formula teaches nonspecific substitution, allowing X to be either one or two carbons away from the nearest carboxy group. Nitro-suberic acid includes a nitro group (X) one carbon from the nearest carboxy group. Slagel teaches that the polyester glycols have a molecular weight of about 1,250-2,000 (col. 6, lines 30-32). Slagel further teaches use of diethylene glycol, which reads on the first claimed formula where o=2 (col. 6, line 43). One of ordinary skill in the art will at once recognize that molecular weight is directly controlled by the number of repeating units present in a polymer. It would have been obvious to one of ordinary skill in the art at the time of filing to finetune the number of repeating units in the polyester diol resulting from modification of Slagel in Hackl and Yao to achieve the desired molecular weight of 1,250-2,000, thereby arriving at the claimed number of repeat units. Claim 36, 47, 51, and 53 are rejected under 35 U.S.C. 103 as being unpatentable over Hackl in view of Yao, and further in view of Prissok (US 11,053,368 B2). Regarding claims 36, 47, 51, and 53, Hackl in view of Yao remains as applied to claim 29 above. However, Kaufhold and Yao are silent as to use of the composition to make a foam. In a similar field of endeavor, Prissok teaches formation of expandable foam beads made of polyurethane that are further heated to form an expanded foam product (col. 5, lines 15-30). Prissok also teaches use of 5-80% by weight of fillers (col. 4, line 35). This prior art range overlaps the claimed range of less than 20 wt%. A prima facie case of obviousness exists where the prior art range overlaps the claimed range. See MPEP 2144.05. Prissok further teaches use of blowing agents in the expandable composition, including halogenated hydrocarbons or saturated aliphatic hydrocarbons having from 3 to 8 carbon atoms (col. 6, lines 8-16). It would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to subject the composition of Hackl in view of Yao to the process of Prissok to arrive at the claimed invention, and to achieve a foam that can be produced at low temperatures, as taught by Prissok (col. 2, lines 1-4). Claim 40 is rejected under 35 U.S.C. 103 as being unpatentable over Hackl in view of Yao, and further in view of Kaufhold (US 2001/0053841). Regarding claim 40, Hackl in view of Yao remains as applied to claim 36 above. Kaufhold (US 2001/0053841) teaches a thermoplastic polyurethane (Abstract) used to form passenger airbags (p. 1, [0002]). The polyurethane is formed from a polyester polyol and a diisocyanate (p. 1, [0011]-[0014]). The polyester polyol may be formed from aliphatic dicarboxylic acids and aliphatic diols (p. 2, [0035]). When used in darker colored molding compositions, the aliphatic diols can be replaced in part by aromatic diols (p. 3, [0040]). It would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to combine the composition of Hackl in view of Yao with the aromatic diols of Kaufhold to arrive at the claimed invention, and to expand the utility of Hackl’s composition to darker colored molding applications, as taught by Kaufhold (p. 3, [0040]). Claim 50 is rejected under 35 U.S.C. 103 as being unpatentable over Hackl in view of Yao, and further in view of Sanner (US 2018/0371169 A1) and Andrew (US 2008/0293841 A1). Regarding claim 50, Hackl in view of Yao remains as applied to claim 29 above. However, Hackl and Yao are silent as to the specific variety and content of the flame retardant ingredient that may be used. In a similar composition, Sanner teaches use of a composition having 1 to 99 wt% polyurethane, 1 to 99 wt% polyetherimide, 0.001-10 wt% (1,000-10,000 ppm) flame retardant (claim 12; p. 12, [0079]). This prior art range overlaps the claimed range. A prima facie case of obviousness exists where the prior art range overlaps the claimed range. See MPEP 2144.05. It would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to combine the ingredients of Hackl and Yao with the flame retardant amount of Sanner to arrive at the claimed invention, and to achieve faster or more economical production, as taught by Sanner (p. 1, [0011]). In a similar field of endeavor, Andrew teaches a polyurethane foam composition having tris(2-chloropropyl)phosphate, an organic phosphate, as a flame retardant (p. 3, [0032]). It would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to combine the ingredients of Hackl and Yao with the flame retardant of Andrew in the amount taught by Sanner, to arrive at the claimed invention and to optimize the stability in the isocyanate reactive component, as taught by Andrew (p. 3, [0032]). Response to Arguments Applicant's arguments filed 09 January 2026 have been fully considered but they are not persuasive. Applicant is thanked for noting the typographical error in the rejection of claims 29-33, 41-42, and 46; the error is fixed above. The current Office action is made non-final as the changes/corrections may constitute a new ground of rejection. Applicant argues that the cited references do not teach the claimed structure, on the basis that Hackl does not teach a nitro-substituted diol and Yao only teaches nitro-substituted diacids. While Applicant is correct that neither reference, taken alone, teaches the entire structure, the combined references certainly do. As discussed above in reference to claim 29, selection of Yao’s dicarboxylic acids for use in Hackl in combination with a diol to form a polyester polyol will result in the claimed structure. As such, all claim limitations are taught by the prior art, and the rejection is maintained. Conclusion Any inquiry concerning this communication or earlier communications from the examiner should be directed to ELIZABETH K AMATO whose telephone number is (571)270-0341. The examiner can normally be reached 8:30 am - 4:30 pm M-F. 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, Rob Jones can be reached at (571) 270-7733. 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. ELIZABETH K. AMATO Examiner Art Unit 1762 /ROBERT S JONES JR/Supervisory Patent Examiner, Art Unit 1762
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Prosecution Timeline

Sep 13, 2022
Application Filed
Jun 13, 2025
Non-Final Rejection — §103
Sep 15, 2025
Response Filed
Oct 07, 2025
Final Rejection — §103
Jan 09, 2026
Response after Non-Final Action
Jan 09, 2026
Request for Continued Examination
Jan 13, 2026
Response after Non-Final Action
Mar 05, 2026
Non-Final Rejection — §103 (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

3-4
Expected OA Rounds
82%
Grant Probability
84%
With Interview (+2.1%)
3y 2m
Median Time to Grant
High
PTA Risk
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