Prosecution Insights
Last updated: September 17, 2026
Application No. 18/334,081

CARBOXYLATE SALTS OF AMINE COMPOUNDS AS CURING AGENTS

Non-Final OA §102§103§DOUBLEPATENT
Filed
Jun 13, 2023
Priority
Oct 24, 2022 — provisional 63/380,657
Examiner
KHAN, AMINA S
Art Unit
1761
Tech Center
1700 — Chemical & Materials Engineering
Assignee
Hexcel Corporation
OA Round
1 (Non-Final)
47%
Grant Probability
Moderate
1-2
OA Rounds
0m
Est. Remaining
90%
With Interview

Examiner Intelligence

Grants 47% of resolved cases
47%
Career Allowance Rate
491 granted / 1035 resolved
-17.6% vs TC avg
Strong +43% interview lift
Without
With
+42.9%
Interview Lift
resolved cases with interview
Typical timeline
3y 3m
Avg Prosecution
50 currently pending
Career history
1094
Total Applications
across all art units

Statute-Specific Performance

§101
1.2%
-38.8% vs TC avg
§103
64.4%
+24.4% vs TC avg
§102
9.7%
-30.3% vs TC avg
§112
17.8%
-22.2% vs TC avg
Black line = Tech Center average estimate • Based on career data from 1035 resolved cases

Office Action

§102 §103 §DOUBLEPATENT
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 . Claims 1-3,5,6,9,10,15-19,21-25,27,29, 31 and 32 are pending. Claims 4,7,8,,11-14,20,26,28 and 30 are cancelled. Claims 9,10,15-19,21,22,25,27,29,31 and 32 have been amended. Applicant’s election without traverse of claims 1—3,5,6,9,10,15-19 and 21 in the reply filed on April 24, 2026 is acknowledged. Claims 22-25,27,29,31 and 32 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim. Claim Rejections - 35 USC § 102 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 1,3,5,9 and 19 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Abe (JP 2004277484A). Abe teaches resin compositions comprising polyamidoamine based curing agents containing a aliphatic polyamine such as a polyethylene (m≥1) polyamine (plurality of amine groups) with a carboxylic acid such as a dimer acid (dicarboxylic acid) and combining with a polyepoxy compound such as bisphenol A type epoxy resin. Accordingly the teachings of Abe are sufficient to anticipate the material limitations of the instant claims. 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. Claims 1,2,10,15-19 and 21 are rejected under 35 U.S.C. 103 as being unpatentable over Inoue (JP 2010126832). Inoue teaches a fiber sizing agent comprising an epoxy resin (page 3, paragraph 2 and 4) and a carboxylate salt of an amine wherein the carboxylate salt is derived from polycarboxylic acids such as glutaric or adipic acid or a monocarboxylic acids such as formic, acetic, propionic acids and the amine is a primary amine or secondary amine (page 5, next to last paragraph; page 6, paragraphs 6-8). Inoue teaches dialkyl salts (dilaurylamine or dioctylamine salts; n≥2), alkyl substituted amines salts (octadecylethylamine salt) and unsubstituted alkylamine salts (laurylpropylamine salts, laurylamine monoamine salts) (page 6, paragraph 7-8). Inoue teaches these compounds have applicant’s m=0 and X absent as no PPO pr PEO are present. Inoue teaches a weight ratio of epoxy resin of molecular weight 1000-5000 (page 3, paragraph 4) to amine, for example laurylpropylamine acetate of MW 242.44 g/mol (page 6, paragraph 8) is 0.1/99.9 to 50/50 (page 8, paragraph 1). For a 50:50 weight ratio of epoxy resin: laurylpropylamine acetate the molar ratio is 0.05mol epoxy:0.20 mol laurylpropylamine acetate or 1:4. Inoue does not teach all the claimed limitations in a single embodiment but one of ordinary skill in the art at the time the invention was made could arrive at the claimed invention by selecting from the teachings of Inoue. It would have been obvious to one of ordinary skill in the art at the time the invention was made to select the claimed epoxy resins and carboxylate salts of primary and secondary amines at the claimed ratios from the teachings of Inoue as Inoue teaches these compounds when combined provide fiber sizing agents that facilitate impregnation of matrix resins into the space between fiber bundles and improve the shape stability of the fiber bundle in a composite. Selecting known components at known mixing ratios to produce compositions for the same sizing benefit is obvious through routine experimentation. Claims 1,3,6,10,15,16,18 and 21 are rejected under 35 U.S.C. 103 as being unpatentable over Inoue (US 2017/0029557). Inoue teaches sixing agents for fibers (paragraph 0001, 0298, 0314) comprising epoxy-amine adducts of acetate salts (paragraph 0604-0610, 0429; applicants formula n=0, m=0, Q plurality of amino groups, X absent) combined with epoxy resins for crosslinking (paragraph 0298, 0627). Inoue teaches epoxy amine ratios of 0.05 to 1 (paragraph 0024). Inoue does not teach all the claimed limitations in a single example but one of ordinary skill in the art at the time the invention was made could arrive at the claimed invention by selecting from the teachings of Inoue. It would have been obvious to one of ordinary skill in the art at the time the invention was made to combine the epoxy:amine adducts of Inoue with epoxy resins as Inoue teaches epoxy-amine adducts of acetate salts are effective sizing agents and can be used in combination with epoxy resins to provide crosslinking to the epoxy resins. Regarding claims 15 and 16, these claims if written in independent form would still make R an optional component as n can be zero. Claims 1,3,6,10,15,16,18 and 21 are rejected under 35 U.S.C. 103 as being unpatentable over Inoue (US 2017/0029557) in view of Sakane (US 2016/0369087). Inoue ‘557 is relied upon as set forth above. Inoue ‘557 does not specify epoxy resins. Sakane teaches similar epoxy-amine adducts are effectively blended with epoxy resins in amounts of 0.1-99.9% epoxy-amine adduct to total resin or 0.1-200 parts by weight to 100 parts by weight of the resin (paragraph 0109-0113). Sakane teaches preparing fiber sizing agents from the resins (paragraph 0036). Sakane teaches epoxy amine ratios of 0.05 to 1 (paragraph 0090). It would have been obvious to one of ordinary skill in the art at the time the invention was made to modify the sizing compositions of Inoue ‘557 by incorporating the epoxy resins at the claimed ratios as Sakane teaches similar epoxy-amine adducts are combined with epoxy resins at broad weight ratios of 0.1-99.9% epoxy-amine adduct to total resin, leaving 99.9-0.1% for the epoxy resin which would allow for the claimed epoxy:amine molar ratio of 10:1 to 1:10. Sakane and Inoue also teach epoxy amine ratios of 0.05 to 1 in the epoxy:amine adduct itself. Using the same combination of epoxy resins and epoxy-amine adducts in the same ratios to prepare compositions for the same sizing of fiber utility is obvious. Regarding claims 15 and 16, these claims if written in independent form would still make R an optional component as n can be zero. 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 1-3,5,6,9,10,15-19 and 21 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-3,5,9,10,11,,15,1-19 of copending Application No. 19/346821 (reference application). Although the claims at issue are not identical, they are not patentably distinct from each other because the copending application contains the same combination of epoxy resins with the same carboxylate salts of amine and selection of the concentrations of the copending application permit one of ordinary skill to arrive at the claimed molar ratio of epoxy:amine. It would be obvious to arrive at this ratio through routine experimentation as the same compounds combined are being used for the same purpose of a sizing agent. 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 AMINA S KHAN whose telephone number is (571)272-5573. The examiner can normally be reached Monday-Friday, 9am-5:30pm EST. 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, Angela Brown-Pettigrew can be reached at 571-272-2817. 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. /AMINA S KHAN/Primary Examiner, Art Unit 1761
Read full office action

Prosecution Timeline

Jun 13, 2023
Application Filed
Aug 19, 2026
Non-Final Rejection mailed — §102, §103, §DOUBLEPATENT (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
47%
Grant Probability
90%
With Interview (+42.9%)
3y 3m (~0m remaining)
Median Time to Grant
Low
PTA Risk
Based on 1035 resolved cases by this examiner. Grant probability derived from career allowance rate.

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