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 .
Response to Arguments
In the Office Action dated 18 February 2026, Applicant submits the following:
Claim 1 has been amended to include the limitations previously established by the now canceled claim 4. No new matter has been identified.
Applicant requests the double patenting rejection of claims 1 & 7-10 over claims 1-10 of copending application 17/631,612 is held in abeyance until an indication of allowable matter is present.
The Applicant’s arguments have been fully considered & thoroughly reviewed but are ultimately found unpersuasive in view of the amended claims.
The Applicant argues that inventive formulations present in Tables 1, 2 & 3 (Specification) demonstrate unexpected improvements in onset temperature and/or peak temperature relative to the comparative examples (Remarks, p. 7-9).
The examples in the specification are not commensurate in scope with the claims, and the Applicant has not provided an explanation regarding how the exemplified results could reasonably be extended to the full scope of the claims. Applicant must show unexpected results over the entire claimed range to support unexpected results for the entire range and generic structures. Whether unexpected results are the result of unexpectedly improved results or a property not taught by the prior art, the objective evidence of nonobviousness must be commensurate in scope with the claims which the evidence is offered to support. See MPEP § 716.02(d). The examples are therefore insufficient to establish non-obviousness of the claims
Applicant argues Yoshihiko uses a different epoxy resin system with dicyandiamide as the hardener and a curing accelerator from the imidazole group (Remarks, p. 9, 4th full paragraph), suggesting the proposed modification would not carry a reasonable expectation of success.
A reasonable expectation of success is required, but absolute predictability thereof is not. Examiner maintains that a person of ordinary skill in the art at the time of filing could modify Zgela in view of Yoshihiko as detailed herein and have a reasonable expectation of success, as Zgela teaches everything of the present application (except certain processing conditions) and discloses increased stability from the addition of boronic acid, and Yoshihiko teaches an epoxy resin, dicyandiamide and a hardening promoter mixed at 90°C or less within 4 hours of combining with a substrate. Therefore, one of ordinary skill in the art will recognize that the only difference, effectively, between Zgela & Yoshihiko is that the process conditions of one (Zgela) comprises boronic acid & the other (Yoshihiko) operates at slightly higher temperatures. Further present are disclosures of increased/improved stability resulting from boronic acid (from Zgela) and disclosures of preventing undesirable increases in viscosity resulting from detailed processing conditions (from Yoshihiko). Therefore, provided with the teachings of Zgela & Yoshihiko, one of ordinary skill in the art would have a reasonable expectation of success when carrying out the modification.
The product used as the hardener detailed in the specification of the present application is DYHARD 100S, which is dicyandiamide (p. 21, lines 19 & 20). In the Yoshihiko citation provided by Applicant (see column 7, line 45 to column 8, line 61, in particular column 7, lines 57-60, and column 8, lines 51-53), Yoshihiko details the dicyandiamide as the hardener as well as the hardening promoter. It is only in the comparative examples of Yoshihiko that the hardener consists of dicyandiamide and a compound of imidazoles.
Applicant states the use of boronic acids in the process described by Yoshihiko is thus not suggested (Remarks, p. 10, lines 2-3). Applicant states Yoshihiko is unstable at elevated temperatures as it lacks the claimed boronic acid.
In response to applicant's arguments against the references individually, one cannot show nonobviousness by attacking references individually where the rejections are based on combinations of references. See In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981); In re Merck & Co., 800 F.2d 1091, 231 USPQ 375 (Fed. Cir. 1986).
Applicant concludes by arguing neither Yoshihiko nor Zgela provide any teaching that boronic acids in combination with urea derivatives as curing accelerators are capable of preventing a partial polymerization of epoxy resin compositions when exposed to elevated temperatures in the range of 60 to 100°C for a prolonged time of more than 15 min as presently claimed (Remarks, p. 11, last two paragraphs).
In response to applicant's argument above, the fact that the inventor has recognized another advantage which would flow naturally from following the suggestion of the prior art cannot be the basis for patentability when the differences would otherwise be obvious. See Ex parte Obiaya, 227 USPQ 58, 60 (Bd. Pat. App. & Inter. 1985).
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.
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 1 – 3 & 5 – 10 are rejected under 35 U.S.C. § 103 as being unpatentable over Zgela et al. (WO 2021/023593 A1; referred to herein via the English equivalent: US 2022/0306837 A1) in view of Yoshihiko et al. (US 5,633,042 A).
Regarding claims 1 – 3 & 5, Zgela teaches epoxy resin compositions comprising an epoxy resin, a curing agent, a curing accelerator and a boronic acid (Abstract). Zgela teaches the use of boronic acids of the formula (I) and formula (II) with an epoxy resin, where R1 of formula (I) is an alkyl, hydroxyalkyl or radical of formula (Il), and at least one of R2, R3 & R4 of formula (Il) is not a hydrogen, where R2, R3 & R4 may be hydrogen, fluorine, chlorine, bromine, iodine, cyano, C1 to C5 alkyl, alkoxy, acyl, alkylsulfonyl, aryl, carboxyl, or B(OH)2 (p. 1, [0011]-[0015]). The formulas (I) & (II), as taught by Zgela, read on the formula (I) & (II), resepectively, in the instant claim 1.
Zgela teaches said resin composition further comprises a curing accelerator of the formula (IV) wherein R6 & R7 are a hydrogen or C1-C5 alkyl, and R8 is hydrogen, C1-C15 alkyl, C3-C15 cycloalkyl, aryl, alkylaryl, C1-C15 alkyl substituted with - NHC(O)NR6R7, C3-C15 cycloalkyl substituted with -NHC(O)NR6R7, aryl substituted with -NHC(O)NR6R7, or, alkylaryl substituted with -NHC(O)NR6R7 (p. 1-2, [0016]- [0023]). The curing accelerator, as taught by Zgela, reads on the curing accelerator of formula (Ill) in the instant claim 1.
Zgela teaches suitable curing agents of the formula (Ill) for curing the epoxy resin, citing preferred curing agents as cyanamide or guanidines, in particularly cyanoguanidines or nitroguanidines (p. 5, [(0115]). Of formula (Ill), R40 may be a cyano, nitro, acyl or radical of the formula -(C=X)-R43, where X is an imino or oxygen and R43 is an amino, alkylamino or alkoxy. R41 may be a hydrogen, C1-C5 alkyl, aryl, benzyl, or acyl, and R42 may be a hydrogen or C1-C5 alkyl (p. 5, [0116]-[0121]). The curing agent, as taught by Zgela, reads on the curing agent of formula (IV) in the instant claim 1.
Zgela states the epoxy resin composition may comprise the epoxy, a curing agent and a curing accelerator (p. 1, [0009]). Zgela further teaches said composition may further comprise rheological additives (i.e., flow modifiers) and provides examples of thermoplastic additives suitable for use in this capacity (p. 8, [0203]-[0204]).
As Zgela teaches epoxy resin compositions comprising an epoxy resin, a curing agent, a curing accelerator, with and without a boronic acid, as well as specific formulas for the curing compounds and boronic acid which identically map to their corresponding components & formulas of the present application, Zgela inherently teaches the properties of said compositions, even if said properties were not known or apparent at the time of the invention. Zgela, however, does not teach processing conditions as detailed in claim 1.
In the same field of endeavor, Yoshihiko teaches a manufacturing process for prepregs by using an epoxy resin and a hardener (Abstract). Example 1 demonstrates heating an epoxy resin to 60°C and combining dicyandiamide and a hardening promoter, maintained at 60°C (col. 7, lines 51-62). When disclosing process conditions, Yoshihiko teaches an epoxy resin, dicyandiamide and a hardening promoter are mixed at 90°C or less within 4 hours of combining with a substrate, thereby preventing viscosity from increasing. Increased viscosity leads to deteriorated infiltration of the substrate, leading to inconsistent appearance (col. 27, line 66 —col. 28, line 9).
It would have been obvious to one of ordinary skill in the art at the time of filing to form Zgela’s composition under the conditions taught by Yoshihiko, as these have been shown to be suitable for similar compositions with similar end uses while avoiding undesirable increases in viscosity, and incorporating the boronic acid in the first stage of heating the epoxy resin to hinder polymerization at elevated temperatures, as Zgela explicitly states this resulted in increased stability. It is prima facie obvious to select a known material based on its suitability for its intended use. See MPEP § 2144.07. A prima facie case of obviousness exists where the claimed ranges overlap or lie inside the ranges disclosed by the prior art. See MPEP § 2144.05.
The claimed increase in onset and/or peak temperatures will necessarily be present as the modification of Zgela in view of Yoshihiko as detailed above results in an identical composition to what is claimed. Products of identical chemical compositions cannot have mutually exclusive properties. Where the claimed and prior art products are identical or substantially identical in structure or composition, a prima facie case of obviousness has been established. See MPEP § 2112.01.
Modification of Zgela in view of Yoshihiko as detailed above reads on limitations established by claims 1 – 3 & 5.
Regarding claim 6, maintaining the modification of Zgela in view of Yoshihiko previously detailed, Zgela teaches examples of the thermoplastic polymers suitable for use in the composition, citing phenoxy resins, acrylate, acrylonitrile, polyetherimide, polyetherketone or polysulfone polymers (p. 8, [0203]). It is prima facie obvious to select a known material based on its suitability for its intended use. See MPEP § 2144.07.
Regarding claim 7, maintaining the modification of Zgela in view of Yoshihiko previously detailed, considering boronic acids of formula (I), Zgela teaches R1 may be methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-metylpropyl, n- pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decanyl, hydroxymethyl, 2-hydroxyethyl, 3- hydroxypropyl, 4-hydroxybutyl or 5-hydroxypentyl (p. 3, [0044]). It is prima facie obvious to select a known material based on its suitability for its intended use. See MPEP § 2144.07.
Regarding claim 8, maintaining the modification of Zgela in view of Yoshihiko previously detailed, Zgela teaches R1 of formula (I) may viably be a radical of formula (Il) wherein R2 may be a fluorine, chlorine, bromine, iodine, cyano, C1-C5 alkyl, alkoxy, acyl, alkylsulfonyl, aryl, carboxyl or B(OH)2, and R3 & R4 are hydrogen (p. 3, [0045]-[0047]). It is prima facie obvious to select a known material based on its suitability for its intended use. See MPEP § 2144.07.
Regarding claims 9 & 10, maintaining the modification of Zgela in view of Yoshihiko previously detailed, Zgela teaches suitable amounts of the boronic acid, curing agent & curing accelerator to be used in their inventive epoxy resin composition. Appropriate amounts for the boronic acid of formula (I) are taught to be from 0.05 to 3.0 parts, based on 100 parts by weight of the epoxy resin. Appropriate amounts of the curing accelerator of formula (IV) (corresponding to the curing accelerator of formula (Ill) in the present application) are taught to be from 0.1 to 9 parts, based on 100 parts by weight of the epoxy resin. Appropriate amounts of the curing agent of formula (III) (corresponding to the curing agent of formula (IV) in the present application) are taught to be from 1 to 15 parts, based on 100 parts by weight of the epoxy resin. Also provided by Zgela are appropriate weight ratios of both the curing agent (formula (IIl)) and curing accelerator (formula (IV)) with respect to the amount of boronic acid present. Suitable weight ratios of the curing agent to the boronic acid are from 1:1 - 240:1 and suitable weight ratios of the curing accelerator to the boronic acid are from 0.05:1 - 160:1 (p. 8, [0205]-[0209]).
All ranges as claimed by claims 9 & 10 in the present application are identical to the corresponding ranges previously taught by Zgela. It is prima facie obvious to select a known material based on its suitability for its intended use. See MPEP § 2144.07. A prima facie case of obviousness exists where the claimed ranges overlap or lie inside the ranges disclosed by the prior art. See MPEP § 2144.05.
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 & 7-10 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-10 of copending Application No. 17/631,612.
Although the claims at issue are not identical, they are not patentably distinct from each other for the following reasons.
Regarding claims 1 & 7, Zgela teaches & claims the use of boronic acid (corresponding to formula (I) of the instant application) with an epoxy resin composition, wherein R1 is an alkyl, hydroxyalkyl or a radical of formula (Il) (corresponding to formula (Il) of the instant application), wherein R2, R3 & R4 may be hydrogen, fluorine, chlorine, bromine, iodine, cyano, C1 to C5 alkyl, alkoxy, acyl, alkylsulfonyl, aryl, carboxyl, or B(OH)2, and at least one of R2, R3 & R4 is not hydrogen. Said epoxy resin composition further comprising a curing accelerator of formula (IV) (corresponding to formula (III) of the instant application), wherein R6 & R7 are a hydrogen or C1-C5 alkyl, and R8 is hydrogen, C1-C15 alkyl, C3-C15 cycloalkyl, aryl, alkylaryl, C1-C15 alkyl substituted with -NHC(O)NR6R7, C3-C15 cycloalkyl substituted with -NHC(O)NR6R7, aryl substituted with -NHC(O)NR6R7, or, alkylaryl substituted with -NHC(O)NR6R7 (claim 1).
Zgela further claims the use of a guanidine (corresponding to formula (IV) of the instant application) wherein R40 may be a cyano, nitro, acyl or radical of the formula — (C=X)-R43, where X is an imino or oxygen and R43 is an amino, alkylamino or alkoxy. R41 may be a hydrogen, C1-C5 alkyl, aryl, or acyl, and R42 may be a hydrogen or C1- C5 alkyl (claim 6).
Zgela further claims R1 in formula (1) may be methyl, ethyl, n-propyl, 1- methylethyl, n-butyl, 1-methylpropyl, 2-metylpropyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decanyl, hydroxymethyl, 2-hydroxyethyl, 3-hydroxypropyl, 4-hydroxybutyl or 5-hydroxypentyl (claim 2).
Pertaining to the claimed physical properties; products of identical chemical compositions cannot have mutually exclusive properties. Where the claimed and prior art products are identical or substantially identical in structure or composition, a prima facie case of obviousness has been established. See MPEP § 2112.01.
Regarding claim 8, Zgela teaches & claims R1 of formula (I) being a radical of formula (Il) and at least one of R2, R3 & R4, two of R2, R3 & R4, and R2, R3 & R4 is/are fluorine, chlorine, bromine, iodine, cyano, C1 to C5 -alkyl, alkoxy, acyl, alkylsulfonyl, aryl, carboxyl or B(OH)2 (claims 3-5). When only one or two of R2, R3 & R4 are present in any of the forms listed in the Markush claim, the remaining R-group or R-group(s) are hydrogen. This reads on all the limitations established by the instant claim 8.
Regarding claims 9 & 10, Zgela teaches & claims the curing agent to be present in amounts of 1 to 15 parts, the curing accelerator to be present in amounts of 0.1 to 9 parts, the boronic acid to be present in amounts of 0.05 to 3.0 parts, with respect to 100 parts by weight of the epoxy resin (claim 9). Appropriate weight ratio of curing agent to boronic acid may be from 1:1 to 240:1, & the appropriate weight ratio of curing accelerator to boronic acid may be from 0.05:1 to 160:1 (claim 10). This reads on all the limitations established by the instant claims 9 & 10. It would have been obvious to form the composition according to the claimed method as it expressly states as being suitable for forming said composition. A prima facie case of obviousness exists where the claimed ranges overlap or lie inside the ranges disclosed by the prior art. See MPEP § 2144.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to CHRISTIAAN ROELOFSE whose telephone number is (571)272-2825. The examiner can normally be reached Monday-Friday 8:00-4:00 EST.
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/CHRISTIAAN ROELOFSE/Examiner, Art Unit 1762
/ROBERT S JONES JR/Supervisory Patent Examiner, Art Unit 1762