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 .
Claim Status
Claims 1-20, 22, and 26-27 are pending.
Claims 1-12, 19, 20 and 22 are withdrawn.
Claims 21 and 23-25 are canceled.
Claims 5, 13, 14, 18-20 and 26-27 are currently amended.
Support for the amendment to claim 14 can be found in [p. 0026] of the specification
Claims 13-18 and 26-27 are examined on their merits.
Response to Arguments
The rejections of claims 14 and 18 under 35 U.S.C. 112(b) have been overcome by amendment and the previous rejections have been withdrawn.
The rejection of claim 13 under 35 U.S.C. 112(a) from the office action dated 12/03/25 has been overcome by amendment and the previous rejection is withdrawn.
Applicant’s arguments, see p. 6, filed 04/03/2026, with respect to the rejection(s) of claim(s) 13 under 35 U.S.C. 102(a)(1) as being anticipated by Shaik (WO 2019/142208) have been fully considered and are persuasive. Therefore, the rejection has been withdrawn. However, upon further consideration, a new ground(s) of rejection is made under 35 U.S.C. 103 as being unpatentable over Shaik (WO 2019/142208).
Applicant's arguments filed 04/03/2026 regarding the rejection of claim 13 under U.S.C. 102(a)(1) as being anticipated by Diakoumakos (US 2007/0135588 Al) have been fully considered but they are not persuasive.
Applicants argue that Diakoumakos does not teach 1) that the PHU-epoxy is simultaneously prepared from a monomer mixture, and 2) that the polyhydroxyurethane-epoxy hybrid polymer is not malleable in dry form at room temperature and becomes malleable upon contact with a catalyst or upon heating to a temperature between 70°C and 250°C.
Diakoumakos exemplifies a nanoparticle-containing hybrid polyurethane-epoxy nanocomposite polymer composition, NPUH1, prepared from a mixture of MY-0500CC, MY-0510, triethylene pentaamine, and nano-clays [table 1; table 7, table 8, p. 0062, 0069, 0091-0106]. Diakoumakos cures the NPHU1 composition at room temperature for 1 day and subsequently at elevated temperature for 4 hours [p. 0099-0102; table 9]. The compositions prepared by Diakoumakos have a glass transition temperature of 112 °C and 154 °C, wherein higher cure temperatures result in a composition with higher glass transition temperatures [table 9]. The compositions of Diakoumakos become malleable at the glass transition temperature or above and therefore are not malleable in dry form at room temperature.
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.
Claim 13-18, 26 and 27 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 instant specification describes an aspect, wherein a PHU polymer can be reprocessed at least once through transitioning between a non-malleable state and a malleable state and between a malleable state and a non-malleable state upon exposure to a range of temperatures wherein the rate of transcarbamoylation imparts a malleable state to the polymer, and wherein the PHU polymer comprises a base catalyst wherein the catalyst results in a decrease in the transition temperature relative to the PHU polymer without the catalyst [p. 0026]. The specification further describes, in another aspect, the transition temperature is from about 80 °C to about 250 °C [p. 0026]. The specification also describes a composition comprising a polyhydroxyurethane (PHU) polymer prepared from a reaction system comprising a multivalent cyclic carbonate monomer and a multivalent amine monomer wherein said polyhydroxyurethane polymer is not malleable in dry form at room temperature and said polyhydroxyurethane polymer becomes malleable when said it is in contact with a catalyst or when it is heated to a temperature between 70 °C and 250 °C [p. 0093, 0099, original claim 6]. The specification further describes a PHU-PI and a PHU-PI-epoxy wherein the hybrid polymers are not malleable in dry form at room temperature and said PHU-PI-epoxy hybrid polymer becomes malleable when said it is in contact with a catalyst or when it is heated to a temperature between 70 °C and 250 °C [p. 0105, 0111; original claims 12 and 18].
In light of this, there is no support in the specification regarding a PHU-epoxy that becomes malleable upon contact with a catalyst or upon heating to a temperature between 70 °C and 250 °C as recited in instant claim 13. The dependent claims are rejected since they fail to alleviate the issue.
Claim Rejections - 35 USC § 102
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claim 13 is rejected under 35 U.S.C. 102(a)(1) as being anticipated by Diakoumakos (US 2007/0135588 A1).
Diakoumakos discloses the preparation of a non-isocyanate-based polyurethane- and polyurethane-epoxy network polymeric compositions [abstract].
The composition of Diakoumakos comprises: (a) a polymerizable organic material that bears at least one cyclocarbonate group, (b) a nano-clay, (c) an amine hardener, and (d) a compound containing one or more epoxy group [p. 0018-0023, 0028, 0030, 0033].
Diakoumakos discloses cyclocarbonate compound (a) can be a monomer, dimer, or oligomer [p. 0023]. Diakoumakos discloses preferred cyclocarbonates (a) are those presented in fig. 6, wherein MY-0500CC is a resin represented as a monomer with a cyclocarbonate functionality of 3, and L-803 is a monomer having a cyclocarbonate functionality of 3 [fig. 6, p. 0027]. Diakoumakos discloses the hardener (c) may be any chemical material known in the art for curing cyclocarbonate (a) and epoxy component (d), wherein the hardener (c) is preferably an aliphatic, aromatic, cycloaliphatic di- or poly-amines [p. 0030]. Diakoumakos discloses component (d) may be an any epoxy resin having more than one epoxy groups per molecule [p. 0033].
Diakoumakos exemplifies a nanoparticle-containing hybrid polyurethane-epoxy nanocomposite polymer composition, NPUH1, prepared from a mixture of MY-0500CC, MY-0510, triethylene pentaamine, and nano-clays [table 1; table 7, table 8, p. 0062, 0069, 0091-0106]. Diakoumakos cures the NPHU1 composition at room temperature for 1 day and subsequently at elevated temperature for 4 hours [p. 0099-0102; table 9]. The compositions prepared by Diakoumakos have a glass transition temperature of 112 °C and 154 °C [table 9]. The compositions of Diakoumakos become malleable at the glass transition temperature or above and therefore are not malleable in dry form at room temperature.
Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claims 14-17 and 27 are rejected under 35 U.S.C. 103 as being unpatentable over Diakoumakos (US 2007/0135588 A1)
Regarding claim 14; Diakoumakos exemplifies resin compositions wherein the epoxy component (d) is in excess relative to cyclocarbonate component (a) (0.79 (d):0.13 (a))[example 1, Diakoumakos is silent with respect to a general teaching regarding the molar ratio between epoxide groups and cyclic carbonate groups. However, Diakoumakos teaches epoxy component (d) is optionally included in the composition [p. 0033] Diakoumakos teaches epoxy component (d) may be residual epoxy resin remaining form partial cyclocarbonation of an epoxy resin to form cyclocarbonate component (a), or provided separately [p. 0027]. In light of this, it would have been obvious to one having ordinary skill in the art at the time the invention was filed to prepare the composition of Diakoumakos wherein epoxy component (d) comprises 0% to 85% of the monomer mixture of cyclocarbonate component (a) and epoxy component (d). In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990).
Regarding claims 15-17; Diakoumakos teaches carbon fibers may optionally be present in the composition as thixotropic or rheological control agents [p. 0038-0039, 0046]. In light of this, it would have been obvious to one having ordinary skill in the art to prepare the composition of Diakoumakos with a carbon fiber filler as a thixotropic or rheological control agent.
Furthermore, as Diakoumakos teaches the composition provides a cured product and exemplifies curing of the composition [p. 0048, 0068]. In light of this, it would have been obvious to one having ordinary skill in the art to cure the composition of Diakoumakos when it further comprises a carbon fiber.
Regarding claim 27; Diakoumakos teaches the cyclocarbonate component (a) may have nitrogen-containing groups such as imine groups [p. 0026]. In light of this, it would have been obvious to one having ordinary skill in the art at the time the invention was filed to prepare the composition of Diakoumakos with a imine-containing cyclocarbonate component (a), and the PHU-PI-Epoxy hybrid resin thereof.
Claims 13, 18, 26 and 27 are rejected under 35 U.S.C. 103 as being unpatentable over Shaik (WO 2019/142208).
Regarding claims 13 and 18;Shaik teaches an ambient cured hydroxyl non-isocyanate polyurethane (HNIPU) based coating [abstract]. Shaik teaches the HNIPU binder is obtained by reacting polycyclic carbonates with amines and/or imines to yield a polymer with polyhydroxy urethane groups [p. 26, lines 18-22]. Shaik further teaches the HNIPU binder may be prepared with an optional epoxy resin component [p. 27, ll. 10-25].
Shaik et al teaches HNIPU coating comprising the binder and hardener is cured at room temperature (< 40 °C), wherein the cured composition is scratch resistant, and is therefore not malleable at room temperature [p. 23, ll. 15-25; p. 27, ll. 25-30]. Shaik is silent with respect to a glass transition temperature, or a temperature at which the composition becomes malleable. However, a person with ordinary skill in the art would expect a composition resulting from the teachings of Shaik to obviously embrace embodiments capable of satisfying these properties as the composition of Shaik significantly satisfies the chemical and material limitations (and amounts thereof) of the claimed composition.
Regarding claims 26 and 27; Shaik teaches a preferred hardener comprises Schiff base adducts of polyimine and polyaldehyde [p. 18, ll. 1-20; p. 23, ll. 9-25]. In light of this, it would have been obvious to one having ordinary skill in the art to prepare the composition of Shaik with a polyimine and/or polyaldehyde hardener.
Claim 26 is rejected under 35 U.S.C. 103 as being unpatentable over Diakoumakos (US 2007/0135588 A1) in view of Shaik (WO 2019/142208).
Regarding claim 26; Diakoumakos teaches optional components include reactive diluents such as additional hardeners, toughening agents, or other additives commonly used in adhesives, sealants, paints/coatings, casting resins, cables, in shapable molding materials and in finished moldings or in composite materials [p. 0030, 0033, 0038-0047]. However, Diakoumakos is silent with respect to additional aldehyde-containing components.
Shaik teaches a non-isocyanate polyurethane coating composition. Shaik teaches additional aldehyde-containing hardener species improved drying of the composition as well as performance properties in terms of hardness and scratch resistance [p. 25, ll. 4-12].
In light of this, it would have been obvious to one having ordinary skill in the art at the time the invention was filed to prepare the composition of Diakoumakos with an additional aldehyde hardening agent in order to improve the physical properties of the cured composition.
Conclusion
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). 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 HOLLEY GRACE HESTER whose telephone number is (703)756-5435. The examiner can normally be reached Monday - Friday 9:00AM -5:00PM.
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/HOLLEY GRACE HESTER/Examiner, Art Unit 1766
/RANDY P GULAKOWSKI/Supervisory Patent Examiner, Art Unit 1766
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