Prosecution Insights
Last updated: April 19, 2026
Application No. 16/895,492

POLYESTER POLYOL COMPOSITIONS CONTAINING HFO-1336MZZM (Z)

Final Rejection §103
Filed
Jun 08, 2020
Examiner
RIETH, STEPHEN EDWARD
Art Unit
1759
Tech Center
1700 — Chemical & Materials Engineering
Assignee
Honeywell International Inc.
OA Round
6 (Final)
44%
Grant Probability
Moderate
7-8
OA Rounds
3y 3m
To Grant
77%
With Interview

Examiner Intelligence

Grants 44% of resolved cases
44%
Career Allow Rate
283 granted / 637 resolved
-20.6% vs TC avg
Strong +32% interview lift
Without
With
+32.5%
Interview Lift
resolved cases with interview
Typical timeline
3y 3m
Avg Prosecution
64 currently pending
Career history
701
Total Applications
across all art units

Statute-Specific Performance

§101
0.6%
-39.4% vs TC avg
§103
38.8%
-1.2% vs TC avg
§102
15.9%
-24.1% vs TC avg
§112
30.2%
-9.8% vs TC avg
Black line = Tech Center average estimate • Based on career data from 637 resolved cases

Office Action

§103
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 Any rejections and/or objections made in the previous Office action and not repeated below are hereby withdrawn. No new ground(s) of rejection are presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Claim Rejections - 35 USC § 103 Claims 16 and 17 is/are rejected under 35 U.S.C. 103 as being unpatentable over Hulse (US 2012/0004299 A1). Regarding Claims 16 and 17, Hulse teaches azeotropes of cis-1,1,1,4,4,4-hexafluoro-2-butene and alcohol (Abstract) and describes polyol premix composition obtained by mixing cis-1,1,1,4,4,4-hexafluoro-2-butene, aromatic polyester polyol, and ethanol (¶ 84-87). Hulse describes methanol or ethanol as being particularly preferred (¶ 6). Propanol is also described (¶ 34). The genus “propanol” only contains two isomers: n-propanol and isopropanol. Since the genus “propanol” is so small, one of ordinary skill would at once envisage each isomer of propanol, including isopropanol. The combination of references would suggest no other blowing agent but cis-1,1,1,4,4,4-hexafluorobut-2-ene, thus meeting the transitional phrase “consisting essentially of”. With regards to the claimed phase separation properties, Hulse teaches examples where the premixes contain 187.2 parts by weight of non-blowing agent/alcohol components, 0.698 parts by mole of cis-1,1,1,4,4,4-hexafluoro-2-butene (equivalent to 114.5 parts by weight), and 2 wt% relative to blowing agent+alcohol of ethanol (equivalent to 2.3 parts by weight) (¶ 85-87). Thus, the embodiment of Hulse is seen to have 0.76 wt% of alcohol. In comparison, the instant specification at ¶ 30 indicates 0.1-10 wt% procure enhanced phase separation properties. See also ¶ 120 and Tables 7A-7C which illustrate 0.56 wt% of ethanol or methanol gives the enhanced phase separation properties. Accordingly, since Hulse describes the same blowing agent and same alcohol being used with polyester polyols within substantially the same concentrations, it is concluded that the stabilization characteristics of the claims are necessarily exhibited by Hulse’s compositions in the absence of evidence to the contrary. The particular embodiment of Hulse differs from the subject matter claimed in that the 0.76 wt% concentration falls outside the range claimed. In this regard, Hulse’s example uses 187.2 parts by weight of non-blowing agent/alcohol components, 0.698 parts by mole of cis-1,1,1,4,4,4-hexafluoro-2-butene (equivalent to 114.5 parts by weight), and 2 wt% relative to blowing agent+alcohol of ethanol (equivalent to 2.3 parts by weight) (¶ 85-87), equivalent to roughly 38.3 wt% of HFO-1336mzzm/alcohol azeotrope. Hulse teaches the blowing agent/alcohol azeotrope may contain greater than zero to about 99 wt% of blowing agent and about 1 wt% to less than 100 wt% of alcohol (¶ 6). Therefore, Hulse is seen to suggest concentrations that 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 Hulse suggests the claimed ranges. A person of ordinary skill would be motivated to use the claimed amount, based on the teachings of Hulse. See MPEP 2123. Claims 1, 4, 5, 7, 8, 11-14, 19, and 20 is/are rejected under 35 U.S.C. 103 as being unpatentable over Hulse (US 2012/0004299 A1) in view of Ionescu (Chemistry and Technology of Polyols for Polyurethanes). Regarding Claims 1, 4, 5, 7, 8, 11, and 12, Hulse teaches azeotropes of cis-1,1,1,4,4,4-hexafluoro-2-butene and alcohol (Abstract) and describes polyol premix composition obtained by mixing cis-1,1,1,4,4,4-hexafluoro-2-butene, aromatic polyester polyol, and ethanol (¶ 84-87). Hulse describes methanol or ethanol as being particularly preferred (¶ 6). Propanol is also described (¶ 34). The genus “propanol” only contains two isomers: n-propanol and isopropanol. Since the genus “propanol” is so small, one of ordinary skill would at once envisage each isomer of propanol, including isopropanol. The combination of references would suggest no other blowing agent but cis-1,1,1,4,4,4-hexafluorobut-2-ene, thus meeting the transitional phrases “consisting essentially of” and “consisting of”. With regards to the claimed phase separation properties, Hulse teaches examples where the premixes contain 187.2 parts by weight of non-blowing agent/alcohol components, 0.698 parts by mole of cis-1,1,1,4,4,4-hexafluoro-2-butene (equivalent to 114.5 parts by weight), and 2 wt% relative to blowing agent+alcohol of ethanol (equivalent to 2.3 parts by weight) (¶ 85-87). Thus, the embodiment of Hulse is seen to have 0.76 wt% of alcohol. In comparison, the instant specification at ¶ 30 indicates 0.1-10 wt% procure enhanced phase separation properties. See also ¶ 120 and Tables 7A-7C which illustrate 0.56 wt% of ethanol or methanol gives the enhanced phase separation properties. Accordingly, since Hulse describes the same blowing agent and same alcohol being used with polyester polyols within substantially the same concentrations, it is concluded that the stabilization characteristics of the claims are necessarily exhibited by Hulse’s compositions in the absence of evidence to the contrary. The foam composition of Hulse differs from the subject matter claimed with respect to the relative amount of aromatic polyester polyol and alcohol, whereby Hulse’s example uses roughly 43.8 wt% of polyester polyol relative to the total quantity of polyols that include other polyols such as Mannich polyol whereas the claims require at least 50 wt%. With respect to alcohol, Hulse’s example uses 187.2 parts by weight of non-blowing agent/alcohol components, 0.698 parts by mole of cis-1,1,1,4,4,4-hexafluoro-2-butene (equivalent to 114.5 parts by weight), and 2 wt% relative to blowing agent+alcohol of ethanol (equivalent to 2.3 parts by weight) (¶ 85-87), equivalent to roughly 38.3 wt% of HFO-1336mzzm/alcohol azeotrope. Hulse teaches the blowing agent/alcohol azeotrope may contain greater than zero to about 99 wt% of blowing agent and about 1 wt% to less than 100 wt% of alcohol (¶ 6). Therefore, Hulse is seen to suggest concentrations that 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 Hulse suggests the claimed ranges. A person of ordinary skill would be motivated to use the claimed amount, based on the teachings of Hulse. See MPEP 2123. With respect to polyester, Ionescu teaches it is known that the structure/amount of polyols used in the creation of rigid polyurethane foams have a significant impact on the resulting foam structure (Pages 535-540). Ionescu in particular indicates the cohesive energy of ester/aromatic units from polyester polyol or Mannich polyols generally confers higher rigidity and dimensional stability (Pages 538-540). Accordingly, it is understood that the relative quantity of aromatic polyester polyol is a result effective variable subject to routine optimization by one of ordinary skill in the art since changing it would clearly affect the type of product obtained. 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 workable or optimal contents of aromatic polyester polyol within the scope of the present claims so as to produce desirable rigidity and dimensional stability characteristics within the resulting foam. Regarding Claims 13 and 14, although the amount of distribution enhancing component is outside the range claimed, Hulse’s example uses 187.2 parts by weight of non-blowing agent/alcohol components, 0.698 parts by mole of cis-1,1,1,4,4,4-hexafluoro-2-butene (equivalent to 114.5 parts by weight), and 2 wt% relative to blowing agent+alcohol of ethanol (equivalent to 2.3 parts by weight) (¶ 85-87), equivalent to roughly 38.3 wt% of HFO-1336mzzm/alcohol azeotrope. Hulse teaches the blowing agent/alcohol azeotrope may contain greater than zero to about 99 wt% of blowing agent and about 1 wt% to less than 100 wt% of alcohol (¶ 6). Therefore, Hulse is seen to suggest blowing agent / distribution enhancing component concentrations that 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 Hulse suggests the claimed ranges. A person of ordinary skill would be motivated to use the claimed amount, based on the teachings of Hulse. See MPEP 2123. With respect to polyester quantity, Ionescu teaches it is known that the structure/amount of polyols used in the creation of rigid polyurethane foams have a significant impact on the resulting foam structure (Pages 535-540). Ionescu in particular indicates the cohesive energy of ester/aromatic units from polyester polyol or Mannich polyols generally confers higher rigidity and dimensional stability (Pages 538-540). Accordingly, it is understood that the relative quantity of aromatic polyester polyol is a result effective variable subject to routine optimization by one of ordinary skill in the art since changing it would clearly affect the type of product obtained. 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 workable or optimal contents of aromatic polyester polyol within the scope of the present claims so as to produce desirable rigidity and dimensional stability characteristics within the resulting foam. Regarding Claims 19 and 20, Hulse teaches foamable compositions comprising polyol premix and polyisocyanate (¶ 75-87). Hulse indicates MDI is used as polyisocyante (¶ 85), which is methylenebis(phenyl isocyanate). Response to Arguments Applicant's arguments filed 10/14/2025 have been fully considered but they are not persuasive. Applicant argues all claims require that at least 50% of the polyol in the polyol premix is polyester polyol. The Examiner notes independent claim 16 contains no such requirement. Applicant argues the present claims are able to unexpectedly provide stability enhancements to polyol blends of 50% or more of polyester polyol with cis-1336 blowing agent owing to the further inclusion of alcohol. This is not found persuasive. Firstly, the closest prior art, Hulse, describes examples using substantial quantities (43.8 wt%) of polyester polyol relative to the total quantity of polyols that include other polyols such as Mannich polyol. Hulse’s examples include ethanol, which is an identical distribution enhancing component used within the specification. It is unclear how or why the enhanced stability characteristic alleged to be unexpected by Applicant is not already present within the disclosure of Hulse. Looking to the experimental data of record, the data only probes polyol blends with 100 wt% polyester polyol and a blowing agent consisting of 1336mzzm(Z). Notably, Table 4 indicates 1336mzzm(Z) achieves uniform blends in some cases where blowing agent is present at up to 8.8 wt% even without compatibilizer. Table 6 indicates higher quantities of 1336mzzm(Z) (~ 22.7 wt%) can be incorporated by addition of stabilizer. Thus, it seems the data only shows the compatibilizer affording stabilization characteristics in compositions with 100 wt% polyester polyol with relatively high 1336mzzm(Z) quantities. The claims at issue are not commensurate in scope with such alleged unexpected results since 1) only “at least 50 wt%” of polyester is polyol is required, 2) the halogenated blowing agent need only comprise small quantities of 1336mzzm(Z), and 3) no particular restriction with respect to blowing agent content is specified. 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 STEPHEN E RIETH whose telephone number is (571)272-6274. The examiner can normally be reached Monday - Friday, 8AM-4PM Mountain Standard Time. 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, Duane Smith can be reached at (571)272-1166. 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. /STEPHEN E RIETH/Primary Examiner, Art Unit 1759
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Prosecution Timeline

Jun 08, 2020
Application Filed
Apr 01, 2022
Non-Final Rejection — §103
Sep 06, 2022
Response Filed
Dec 10, 2022
Final Rejection — §103
May 15, 2023
Request for Continued Examination
May 31, 2023
Response after Non-Final Action
Jun 01, 2023
Response after Non-Final Action
Nov 29, 2023
Non-Final Rejection — §103
Jun 04, 2024
Response after Non-Final Action
Jun 04, 2024
Response Filed
Jul 09, 2024
Response Filed
Sep 25, 2024
Final Rejection — §103
Mar 26, 2025
Request for Continued Examination
Mar 29, 2025
Response after Non-Final Action
Apr 09, 2025
Non-Final Rejection — §103
Oct 14, 2025
Response Filed
Oct 22, 2025
Response after Non-Final Action
Mar 04, 2026
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

7-8
Expected OA Rounds
44%
Grant Probability
77%
With Interview (+32.5%)
3y 3m
Median Time to Grant
High
PTA Risk
Based on 637 resolved cases by this examiner. Grant probability derived from career allow rate.

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