Prosecution Insights
Last updated: September 17, 2026
Application No. 18/687,032

ULTRA-SHORT HYDROPHOBE ALKOXYLATES AS SOLVENTS OR COSOLVENTS

Non-Final OA §102§DP
Filed
Feb 27, 2024
Priority
Aug 27, 2021 — provisional 63/237,892 +1 more
Examiner
RUNYAN, SILVANA C
Art Unit
Tech Center
Assignee
Harcros Chemicals Inc.
OA Round
1 (Non-Final)
82%
Grant Probability
Favorable
1-2
OA Rounds
0m
Est. Remaining
99%
With Interview

Examiner Intelligence

Grants 82% — above average
82%
Career Allowance Rate
873 granted / 1059 resolved
+22.4% vs TC avg
Strong +17% interview lift
Without
With
+17.0%
Interview Lift
resolved cases with interview
Fast prosecutor
2y 2m
Avg Prosecution
43 currently pending
Career history
1113
Total Applications
across all art units

Statute-Specific Performance

§101
1.3%
-38.7% vs TC avg
§103
44.9%
+4.9% vs TC avg
§102
25.9%
-14.1% vs TC avg
§112
19.7%
-20.3% vs TC avg
Black line = Tech Center average estimate • Based on career data from 1059 resolved cases

Office Action

§102 §DP
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 . Election/Restrictions Applicant’s election without traverse of Group I. Applicant elects Group A, claim 10 (Formula VIII), BO: -CH₂-CH(ethyl)-O-, and R¹ is C1-C₈ alkyl group, claims 1-7, 9, and 10 , in the reply filed on 08/28/2026 is acknowledged. Furthermore, since the applicant has selected the above species, the remaining species could be presented in a divisional or continuation applications. Information Disclosure Statement The listing of references in the specification is not a proper information disclosure statement. 37 CFR 1.98(b) requires a list of all patents, publications, or other information submitted for consideration by the Office, and MPEP § 609.04(a) states, "the list may not be incorporated into the specification but must be submitted in a separate paper." Therefore, unless the references have been cited by the examiner on form PTO-892, they have not been considered. Specification The title of the invention is not descriptive. A new title is required that is clearly indicative of the invention to which the claims are directed. Claim Rejections - 35 USC § 102 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 the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action: A person shall be entitled to a patent unless – (a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention. Claims 1-7, 9, and 10 are rejected under 35 U.S.C. 102(a) (1) as anticipated by or, in the alternative, under 35 U.S.C. 103 as obvious over Weerasooriya et al. (US 2016/0264847 A1 ) “Weerasooriya” herein – provided by applicant) (Claims contain only selected species) Claim 1 Weerasooriya discloses a compound defined by Formula I, PNG media_image1.png 74 226 media_image1.png Greyscale wherein BO represents -CH₂-CH(ethyl)-O- ; PO represents -CH₂-CH(methyl)-O-; EO represents -CH₂-CH₂-O-; R¹ represents a C1-C₈ alkyl group; n is an integer from 2 to 6; X is an integer from 0 to 5; y is an integer from 1 to 10; and Z is an integer from 0 to 50. [0005-0007, 0055-0062] Or a different interpretation of Weerasooriya Weerasooriya discloses a compound defined by Formula I, PNG media_image1.png 74 226 media_image1.png Greyscale wherein BO represents -CH₂-CH(ethyl)-O- ; PO represents -CH₂-CH(methyl)-O-; EO represents -CH₂-CH₂-O-; R¹ represents a C1-C₈ alkyl group; n is an integer from 2 to 6; X is an integer from 0 to 5; y is an integer from 1 to 10; and Z is an integer from 0 to 50. [0005-0007, 0055-0062] Weerasooriya does not explicitly disclose the terminology as recited within the claimed invention: Formula I. However, Weerasooriya the short hydrophobe anionic surfactants can be defined by Formula II below PNG media_image2.png 84 428 media_image2.png Greyscale where R.sup.1 is a C.sub.7-C.sub.12 alkyl group,; m is an integer from 2 to 24 and n is an integer from 0 to 22, with the proviso that m+n is from 2 to 24; X is —CH.sub.2C(O)O.sup.−M.sup.+, —CH.sub.2C(O)OH; and M.sup.+ is a cation. In some cases, m can be from 2 to 15 and/or n can be from 0 to 10. In certain cases, m can be an integer from 3 to 10 and n can be an integer from 0 to 10, and the sum of m and n (m+n) can be from 3 to 15. In certain embodiments, the short hydrophobe anionic surfactant can be a carboxylate surfactant (e.g., X can be —CH.sub.2C(O)O.sup.−M.sup.+, —CH.sub.2C(O)OH). In certain embodiments, R.sup.1 can be a branched C.sub.7-C.sub.12 alkyl group (e.g., a 2-ethylhexyl group)., cation, I ([0006] ) which serves as the compound of formula I. Therefore, the Examiner interprets this disclosure to read on the claimed invention. Claim 2. Weerasooriya discloses the compound of claim 1, wherein n is an integer from 3 to 6. [0005-0007, 0055-0062] Claim 3. Weerasooriya discloses the compound of claim1, wherein y is an integer from 2 to 10. [0005-0007, 0055-0062] Claim 4. Weerasooriya discloses the compound of claim 1, wherein y is from 3 to 6. [0005-0007, 0055-0062] Claim 5. Weerasooriya discloses the compound of claim1, wherein R¹ is a C₁-C₆ alkyl group. [0005-0007, 0055-0062] Claim 6. Weerasooriya discloses the compound of claim 1, wherein Z is greater than 1. [0005-0007, 0055-0062] Claim 7. Weerasooriya discloses the compound of claim 1, wherein Z is an integer from 1 to 40. [0005-0007, 0055-0062] Claim 9. Weerasooriya discloses the compound of claim 1, wherein n is 3. [0005-0007, 0055-0062] Claim 10. Weerasooriya discloses the compound of claim 9, wherein the compound is defined by Formula II wherein PNG media_image3.png 120 196 media_image3.png Greyscale BO represents -CH₂-CH(ethyl)-O-; PO represents -CH₂- CH(methyl)-O-; EO represents -CH₂-CH₂-O-; X is an integer from 0 to 5; y is an integer from 1 to 10; and Z is an integer from 0 to 50. [0005-0007, 0055-0062] Claims 1-7, 9, and 10 are rejected under 35 U.S.C. 102(a) (1) as anticipated by or, in the alternative, under 35 U.S.C. 103 as obvious over Gatto et al. US 2008/0200894 A1) (“Gatto” herein) Claim 1. Gatto discloses a compound defined by Formula I, PNG media_image1.png 74 226 media_image1.png Greyscale wherein BO represents -CH₂-CH(ethyl)-O- ; PO represents -CH₂-CH(methyl)-O-; EO represents -CH₂-CH₂-O-; R¹ represents a C1-C₈ alkyl group; n is an integer from 2 to 6; X is an integer from 0 to 5; y is an integer from 1 to 10; and Z is an integer from 0 to 50. [0030-0037] Or a different interpretation of Gatto Gatto discloses a compound defined by Formula I, PNG media_image1.png 74 226 media_image1.png Greyscale wherein BO represents -CH₂-CH(ethyl)-O- ; PO represents -CH₂-CH(methyl)-O-; EO represents -CH₂-CH₂-O-; R¹ represents a C1-C₈ alkyl group; n is an integer from 2 to 6; X is an integer from 0 to 5; y is an integer from 1 to 10; and Z is an integer from 0 to 50. [0029-0037] Gato however does not explicitly disclose the terminology as recited within the claimed invention: Formula I. However, Gatto discloses that the PPG materials suitable herein include PPG homopolymer materials, PPG copolymer materials, and PPG surfactant materials, as well as mixtures thereof. Suitable PPG homopolymer materials include those corresponding to the following formula: PNG media_image4.png 90 268 media_image4.png Greyscale wherein R is hydrogen, methyl, ethyl, propyl, isopropyl, butyl,..[0029, 0031] wherein n is from 3 to 160, preferably from 10 to 100, and more preferably from 20 to 80. Optionally, the PPG homopolymer may include low level of glycerol or butanediol as part of its monomer raw material. Suitable PPG copolymer materials include those in which the polyprolyene glycol segments are present as an internal block component and/or as a terminal component, of the copolymer structure. The following formulae illustrate the internal block components and terminal block components: PNG media_image5.png 146 318 media_image5.png Greyscale wherein x is from 2 to 120, preferably from 2 to 80, and more preferably from 3 to 60; y is from 2 to 100, preferably from 2 to 50, and more preferably from 3 to 30; and R2 is hydrogen, methyl, ethyl, isopropyl or isobutyl. [0036-0037] which serves as the compound of formula I. Therefore, the Examiner interprets this disclosure to read on the claimed invention. Claim 2. Gatto discloses the compound of claim 1, wherein n is an integer from 3 to 6. [0030-0037] Claim 3. Gatto discloses the compound of claim1, wherein y is an integer from 2 to 10. [0030-0037] Claim 4. Gatto discloses the compound of claim 1, wherein y is from 3 to 6. [0030-0037] Claim 5. Gatto discloses the compound of claim1, wherein R¹ is a C₁-C₆ alkyl group. [0030-0037] Claim 6. Gatto discloses the compound of claim 1, wherein Z is greater than 1. [0030-0037] Claim 7. Gatto discloses the compound of claim 1, wherein Z is an integer from 1 to 40. [0030-0037] Claim 9. Gatto discloses the compound of claim 1, wherein n is 3. [0030-0037] Claim 10. Gatto discloses the compound of claim 9, wherein the compound is defined by Formula II below Formula II wherein PNG media_image3.png 120 196 media_image3.png Greyscale BO represents -CH₂-CH(ethyl)-O-; PO represents -CH₂- CH(methyl)-O-; EO represents -CH₂-CH₂-O-; X is an integer from 0 to 5; y is an integer from 1 to 10; and Z is an integer from 0 to 50. [0030-0037] Claims 1-7, 9, and 10 are rejected under 35 U.S.C. 102(a) (1) as anticipated by or, in the alternative, under 35 U.S.C. 103 as obvious over Reese et al. (US 2014/0275312 A1) (“Reese” herein) Claim 1-7, 9, and 10. Reese does not disclose a compound defined by Formula I, PNG media_image1.png 74 226 media_image1.png Greyscale wherein BO represents -CH₂-CH(ethyl)-O- ; PO represents -CH₂-CH(methyl)-O-; EO represents -CH₂-CH₂-O-; R¹ represents a C1-C₈ alkyl group; n is an integer from 2 to 6; X is an integer from 0 to 5; y is an integer from 1 to 10; and Z is an integer from 0 to 50. [0011-0016, ] Reese discloses ¶ [0011-0020, 0038-0042] he present invention relates to long chain polyether polyols which are characterized by a functionality of 2 to 6 and an equivalent weight of 1000 to 2200 Da. These polyether polyols comprise the alkoxylation product of: (1) a starter composition having an equivalent weight of 350 Da or less, which comprises the alkoxylation product of , (a) a low molecular weight polyether having a functionality of 3 and an equivalent weight of less than 350 Da, . (b) at least one low molecular weight starter compound comprising glycerin, and (c) propylene oxide or a mixture of propylene oxide and ethylene oxide, with the weight ratio of propylene oxide to ethylene oxide ranging from 80:20 to 100:0, in the presence of (d) at least one double metal cyanide catalyst; with (2) one or more alkylene oxides, wherein up to 20% of ethylene oxide is added as a cap; in the presence of (3) at least one basic catalyst) Suitable low molecular weight polyether polyols to be used as component (a) of the starter compositions (1) have a functionality of 3 and an equivalent weight of less than 350 Da. Preferably, these low molecular weight polyether polyols have an equivalent weight of from 150 to 280 Da. In a particularly preferred embodiment, the low molecular weight polyether polyol comprises (i) an all propylene oxide, glycerin based polyether polyol having an equivalent weight of about 230 to about 235 or (ii) an all propylene oxide, glycerin based polyether polyol having an equivalent weight of about 330 to about 335. The starter compositions (a) additionally require (2) a low molecular weight starter compound comprising glycerin. In addition, to glycerin, the low molecular weight starter compound may comprise ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, tripropylene glycol, trimethylolpropane, 1,3-butanediol, 1,4-butanediol, pentaerythritol, sorbitol, sucrose, ethylenediamine, toluene diamine, etc. Mixtures of these low molecular weight starter compounds are also suitable. In a preferred embodiment, the low molecular weight starter compound comprises glycerin in the absence of other low molecular weight starter compounds. Component (c) of the starter composition (1) comprises propylene oxide or a mixture of propylene oxide and ethylene oxide, with the weight ratio of propylene oxide to ethylene oxide ranging from 80:20 to 100:0, and preferably from 90:10 to 100:0.). for the purpose of improves the productivity of preparing long chain active polyethers from short chain polyethers. [0010] Accordingly, it would have been obvious to a person of ordinary skill in the art before the effective filling date of the claimed invention to arrive the compound of Formula I with the alkoxylation process as disclosed by Reese, in order to prepare long chain active polyether from short chain polyethers. 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 1-7, 9, and 10 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claim 1-6, and 9-13 of copending Application No. 18/687026 (“’026 “ herein) (reference application). Although the claims at issue are not identical, they are not patentably distinct from each other because the instant application independent claim 1 limitation, including its dependent claims, are included in the copending application ‘026. This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented. Conclusion The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. Wehlan et al. (US 2017/0369440 A1) PROCESS FOR THE PRODUCTION OF 2-[4-(CYCLOPROPANECARBONYL)PHENYL]-2-METHYL-PROPANENITRILE teaches A new process for the production of 2-[4-(cyclopropanecarbonyl)phenyl]-2-methyl-propanenitrile is described. This compound can be used for the production of drugs, such as Fexofenadine, Boutuettaya et al. (US 2021/0079154 A1) A POLYISOCYANATE FOAM FOR SANDWICH PANEL WITH LOW PROCESSING TEMPERATURE AND ENHANCED ADHESION teaches Described herein are a polyisocyanurate foam, its use in a sandwich panel, a sandwich panel including the foam, and a process for preparing the sandwich panel. The polyisocyanurate foam shows a good adhesion property even without adhesion promoter, improved processability of PIR systems at lower temperature (≤50° C.), and an improved flame resistance property, and Miller et al. (US 2020/0255624 A1) LATEX STABILIZER FOR SYNTHETIC LATEX AND METHODS OF USE teaches Provided are compositions, systems, and methods of using a synthetic latex composition for treating a subterranean formation. An example method comprises providing a synthetic latex composition comprising: a synthetic latex and a latex stabilizer; and exposing the synthetic latex composition to air for an exposure period of at least one day; wherein the synthetic latex composition loses less than 5% of its initial water concentration at the end of a one-day exposure period. The synthetic latex composition may be further included in a treatment fluid. The treatment fluid may be introduced into a wellbore penetrating a subterranean formation. Any inquiry concerning this communication or earlier communications from the examiner should be directed to SILVANA C RUNYAN whose telephone number is (571)270-5415. The examiner can normally be reached M-F 7:30-4:30. 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, Sue Liu can be reached at 571-272-5539. 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. /SILVANA C RUNYAN/ Primary Examiner, Art Unit 1616 09/09/2026
Read full office action

Prosecution Timeline

Feb 27, 2024
Application Filed
Sep 11, 2026
Non-Final Rejection mailed — §102, §DP (current)

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Prosecution Projections

1-2
Expected OA Rounds
82%
Grant Probability
99%
With Interview (+17.0%)
2y 2m (~0m remaining)
Median Time to Grant
Low
PTA Risk
Based on 1059 resolved cases by this examiner. Grant probability derived from career allowance rate.

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