DETAILED ACTION
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on October 2, 2025 has been entered.
Claim Objections
Claims 1, 3, 6, 8-18, 21-26 are objected to because of the following informalities: The claim amendments are very blurry and, in some places, illegible. It is suggested to not make amendments with “track changes” on, or with the amendments in a color other than black because it appears those are the most likely scenarios when the text is blurry. Appropriate correction is required.
Claim Rejections - 35 USC § 112
The following is a quotation of the first paragraph of 35 U.S.C. 112(a):
(a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.
The following is a quotation of the first paragraph of pre-AIA 35 U.S.C. 112:
The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor of carrying out his invention.
Claims 1, 3, 6, 8-18, and 21-26 are rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, as failing to comply with the written description requirement. The claim(s) contains subject matter which was not described in the specification in such a way as to reasonably convey to one skilled in the relevant art that the inventor or a joint inventor, or for applications subject to pre-AIA 35 U.S.C. 112, the inventor(s), at the time the application was filed, had possession of the claimed invention. The subject matter which was not described in the specification is that the thermoset composition has an imine content characterized by combination of the backbones with a molar excess of amine groups relative to the epoxy groups. The specification at published paragraph 72 states the epoxy:NH molar ratio is 1:5 to 5:1. However, this range does not cover the entire scope of “molar excess of amine groups relative to epoxy groups, for example 1:6 epoxy:NH is a molar excess of amine groups relative to epoxy groups, but is not part of the disclosed range.
Further in claim 22, there is no support for the amine hardener comprising a polymer terminated by amine groups. While poly(propylene glycol) bis(2-aminopropyl ether) may be a polymer terminated by amine groups, any other polymers terminated by amine groups are not disclosed.
In claim 23, there is no support for the amine hardener comprising a polyetheramine.
In claim 26, there is no support for the cross link density being less than 3.53 10-3 mol/cm-3. This value is a point of data in table 1, but all values that are less than 3.53 10-3 mol/cm-3 are not disclosed.
If applicant believes there is support for these amendments, the examiner requests the applicant to cite the passages with paragraph numbers to show the support.
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 9-18, 21-23, 25 and 26 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Regarding claim 9: The limitation that discusses the amine hardener: “and in an amount that provides a molar excess of amine groups relative to the epoxy groups” is unclear since it is indefinite how much amine hardener is required when the backbones are terminated by aldehyde groups instead of epoxy groups.
Regarding claim 25: Claim 1, from which claim 25 depends, requires a molar excess of amine groups relative to epoxy groups. Therefore, less than 2:1 of epoxy groups to amine groups is broader than the claim from which claim 25 depends since this is not a molar excess of amine groups.
Regarding claim 26: Claims should be one sentence in length. Therefore, the period after °C in the second to the last line is unclear. Further, Tα is not defined and φ is not defined when not using the Flory theory. It is unclear if the Flory theory is being used.
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.
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, 6, 8-12, 14-18, and 21-26 are rejected under 35 U.S.C. 103 as being unpatentable over Mikroyannidis, “Epoxides Bearing Azomethine Linkages”, Polymer International, 1991, pp. 91-97, Vol. 25, No. 2 in view of Webster et al. (WO 2016/172353).
Regarding claims 1 and 25: Mikroyannidis teaches a composition comprising an epoxy having the structure:
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(page 92, scheme 1). This is a backbone having a single imine bond which bonds aromatic compounds together. Since Z can be either hydrogen or a glycidyl epoxy group, it can be considered to be two different backbones, both with a single imine bond bonding aromatic compounds together. Alternatively, claim 1 does not require the first backbone to be a different compound than the second backbone. Mikroyannidis also teaches the epoxies are polymerized with a DDS curing agent (page 95 second column). DDS is diaminodiphenylsulfone, which is an amine.
Mikroyannidis does not teach a molar excess of amine groups to epoxy groups. However, Webster et al. teaches a crosslinking of glycidated vanillin with a diamine where there is a 1:2 epoxy to amine ratio (para. 61). Mikroyannidis and Webster et al. are analogous art since they are both concerned with the same field of endeavor, namely epoxies having aromatic groups and imine bonds that are crosslinked with amines. Before the effective filing date of the claimed invention a person having ordinary skill in the art would have found it obvious to have an amine excess and would have been motivated to do so in order to control the hardness of the product.
Regarding claim 3: Mikroyannidis teaches the basic claimed composition as set forth above. Not disclosed is the filler. However, Webster et al. teaches a similar reaction containing a plasticizer (para. 34). Before the effective filing date of the claimed invention a person having ordinary skill in the art would have found it obvious to use the plasticizer of Webster et al. in the composition of Mikroyannidis and would have been motivated to do so to make the product more flexible.
Regarding claim 6: Mikroyannidis teaches the basic claimed composition as set forth above. Not disclosed is the water-resistant coating disposed on the thermoset composition. However, Webster et al. teaches a water-resistant coating on the thermoset, such as glass (para. 33). Before the effective filing date of the claimed invention a person having ordinary skill in the art would have found it obvious to add the glass layer of Webster et al. to the composition of Mikroyannidis and would have been motivated to do so to give the product some structure.
Regarding claim 8: Mikroyannidis teaches the basic claimed composition as set forth above. Not disclosed is the poly(propylene glycol bis(2-aminopropyl ether). However, Webster et al. teaches Jeffamine D230 (para. 61), which has this structure. Before the effective filing date of the claimed invention a person having ordinary skill in the art would have found it obvious to use Jeffamine D230 of Webster et al. in the composition of Mikroyannidis and would have been motivated to do so since Webster et al. teaches it has good cure behavior in a similar system (table 2).
Regarding claims 9-12 and 15-18: Mikroyannidis teaches a composition/system comprising an epoxy having the structure:
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(page 92, scheme 1). The backbones comprise a single imine bond bonding aromatic compounds together, and epoxy groups terminate the backbone. This is the first compound of claim 15. The epoxy groups are glycidyl groups. Mikroyannidis also teaches the epoxies are polymerized with a DDS curing agent (page 95 second column). DDS is diaminodiphenylsulfone, which is an amine.
Mikroyannidis does not teach a molar excess of amine groups to epoxy groups. However, Webster et al. teaches a crosslinking of glycidated vanillin with a diamine where there is a 1:2 epoxy to amine ratio (para. 61). Before the effective filing date of the claimed invention a person having ordinary skill in the art would have found it obvious to have an amine excess and would have been motivated to do so in order to control the hardness of the product.
Regarding claim 14: Mikroyannidis also teaches a precursor having three aromatic rings connected by two imine bonds (scheme 4).
Regarding claims 21-23: Mikroyannidis teaches the basic claimed composition as set forth above. Not disclosed is the poly(propylene glycol bis(2-aminopropyl ether). However, Webster et al. teaches Jeffamine D230 (para. 61), which has this structure, is a polymer terminated by amine groups, and comprises a polyetheramine. Before the effective filing date of the claimed invention a person having ordinary skill in the art would have found it obvious to use Jeffamine D230 of Webster et al. in the composition of Mikroyannidis and would have been motivated to do so since Webster et al. teaches it has good cure behavior in a similar system (table 2).
Regarding claim 24: While Mikroyannidis does not teach the method steps of depolymerization and repolymerization, the claim is directed to a composition and not a method. Therefore, the composition taught by Mikroyannidis and Webster et al., i.e. not depolymerized and repolymerized, would read on the same composition that has undergone depolymerization and repolymerization.
Regarding claim 26: While Mikroyannidis does not explicitly teach the crosslink density, mere recognition of latent properties or additional advantages in the prior art does not render nonobvious an otherwise known invention (MPEP 2145 II).
Claim 13 is rejected under 35 U.S.C. 103 as being unpatentable over Mikroyannidis, “Epoxides Bearing Azomethine Linkages”, Polymer International, 1991, pp. 91-97, Vol. 25, No. 2 in view of Webster et al. (WO 2016/172353) as applied to claim 9 set forth above and in view of Leibler et al. (US 2017/0051083).
Regarding claim 13: Mikroyannidis teaches the claimed precursor having the epoxy groups as end groups. Not disclosed is where one end is an epoxy group and the other end is an aldehyde group. However, Leibler et al. teaches aldehyde groups also react with amines (para. 305). Mikroyannidis and Leibler et al. are analogous art since they are both concerned with the same field of endeavor, namely aromatic imine resins. Before the effective filing date of the claimed invention a person having ordinary skill in the art would have found it obvious to have one aldehyde group and one epoxy group and would have been motivated to do so since both aldehyde and the epoxy can both be cured with an amine curing agent.
Response to Arguments
Applicant's arguments filed October 2, 2025 have been fully considered but they are not persuasive.
Applicant’s argument that there is support for the claimed molar ratio and crosslink density is not persuasive. The specification at published paragraph 72 states the epoxy:NH molar ratio is 1:5 to 5:1. Further, the examples teach 2:1.05 epoxy to NH. However, this range and these points do not cover the entire scope of “molar excess of amine groups relative to epoxy groups, for example 1:6 epoxy:NH is a molar excess of amine groups relative to epoxy groups, but is not part of the disclosed range. In claim 26, there is no support for the cross link density being less than 3.53 10-3 mol/cm-3. This value is a point of data in table 1, but all values that are less than 3.53 10-3 mol/cm-3 are not disclosed.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Megan McCulley whose telephone number is (571)270-3292. The examiner can normally be reached Monday - Friday 9-5:30.
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/MEGAN MCCULLEY/
Primary Examiner, Art Unit 1767