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 1-12 are pending.
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.
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.
Claim(s) 1-2, 5-6, and 9-12 is/are rejected under 35 U.S.C. 103 as being unpatentable over Meegan (US 2021/0403637 A1), and further in view of Kobayashi et al. (US 2021/0122892 A1) and Ponsolle et al (US 2024/0269957 A1).
Regarding claims 1 and 11; Meegan is directed toward a curable resin composition for a fiber reinforce resin matrix composite article, comprising:
at least one epoxy compound having at least two epoxide groups per molecule of the epoxy compound,
at least one multifunctional aromatic amine that forms a crystalline solid at 25° C., and
at least one halo-substituted diethyltoluenediamine, in an amount effective to inhibit crystallization of the at least one multifunctional aromatic amine [p. 0012, 0111].
Meegan teaches the multifunctional aromatic amine may be an alkylene bis-aniline, wherein examples include 4,4′-methylene-bis-(2,6-diethylaniline) (“MDEA”), 4,4′-Methylene-bis-(3-chloro-2,6-diethylaniline (“M-CDEA”), 4,4′-Methylene-bis-(2-isopropyl-6-methylaniline) (“M-MIPA”), and 4,4 Methylenebis(2,6-diisopropylaniline) (“M-DIPA”) [p. 0059-0062].
Meegan teaches the halo-substituted diethyltoluenediamine is selected from the group consisting of 6-chloro-3,5-diethyltoluene-2,4-diamine, 4-chloro-3,5-diethyltoluene-2,6-diamine, 6-chloro-3,5-diethyltoluene-2,4-diamine-4-chloro-3,5-diethyltoluene-2,6-diamine, and mixtures thereof [p. 0078]. Meegan teaches the halo-substituted diethyltoluenediamine inhibits crystallization of the at least one multifunctional aromatic amine component of the curing agent composition to the extent that the curing agent composition of the present invention remains liquid when maintained at temperature greater than or equal to 25° C [p. 0079].
Both the multifunctional aromatic amine and the halo-substituted diethyltoluenediamine are required components in the composition of Meegan. The multifunctional aromatic amine satisfies curing agent A of the claimed invention and the halo-substituted diethyltoluenediamine simultaneously satisfies both curing agent B and C of the claimed invention. Alternatively, combinations of “at least one” of these amines would obviously satisfy the claimed combination of curing agents.
Meegan teaches epoxy compounds of the present invention are saturated or unsaturated aliphatic, cycloaliphatic, aromatic or heterocyclic compounds that have at least two epoxide group per molecule and include aromatic epoxy compounds, epoxy compounds, alicyclic epoxy compounds, and epoxy compounds [p. 0081].
Meegan teaches suitable epoxy compounds for use as the at least one epoxy compound component of the curable resin composition include aromatic compounds having two or more epoxide groups per molecule such as polyglycidal adducts of amines, such as N,N-diglycidyl aniline, N,N,N′,N′-tetraglycidyl diaminodiphenylmethane (TGDDM), triglycidyl aminophenols (TGAP), triglycidyl aminocresol, or tetraglycidyl xylenediamine [p. 0082-0083]. Meegan fails to explicitly disclose the ether structure of N,N,N′,N′-tetraglycidyl diaminodiphenylmethane ether.
However, Kobayashi discloses a related composition and composite (Abstract) and presents claimed epoxy resin D (tetraglycidyl-3,4'-diaminodiphenyl ether) and the tetraglycidyldiamino methane of Meegan as equally suitable tetrafunctional epoxy resins for this type of composition and composite [end of p. 0101]. "It is prima facie obvious to combine two compositions each of which is taught by the prior art to be useful for the same purpose, in order to form a third composition to be used for the very same purpose.... [T]he idea of combining them flows logically from their having been individually taught in the prior art." In re Kerkhoven, 626 F.2d 846, 850, 205 USPQ 1069, 1072 (CCPA 1980).
Meegan teaches the composition may further comprise one or more additives including toughening additives (such as core-shell particles, thermoplastic polymers) [p. 0093].
Meegan teaches fibers suitable for use as the fiber component of the curable fiber reinforced resin matrix composite material include, for example, carbon fibers, graphite fibers, glass fibers, such as E glass fibers, ceramic fibers, such as silicon carbide fibers, synthetic polymer fibers [p. 0098]. The fiber pre-form may comprise any desired configuration of reinforcing fibers, such as, for example, continuous fibers: plies of a unidirectional continuous fiber tape, a 3-dimensional woven fabric, a non-woven discontinuous fiber mat, or a non-crimp fabric (NCF) [p. 0035, 0113]. After combining the curable resin composition and the fiber reinforcement, the curable resin composition is cured at a temperature of 170° C to 180° C to form a fiber reinforce resin matrix composite article [p. 0111, 0125]. Meegan is silent with respect to the melting temperature of the fiber used as the stitch material.
Ponsolle demonstrates that the instantly claimed material is recognized in the art as a suitable stitching material for use in non-crimp fabrics [abstract, p. 0042]. Ponselle teaches a process for manufacturing a NCF comprising [p. 0011-0014]:
a) providing a curable composition, the curable composition comprising a matrix resin and a non-crimp fabric comprising at least one layer of unidirectionally oriented multifilament carbon yarns and a multifilament stitching yarn interlinking the multifilament carbon yarns, wherein the stitching yarn comprises a thermoplastic polymer;
b) heating the curable composition to a temperature T1, wherein T1 is greater than the melting temperature (Tm) of the stitching yarn and wherein the conversion of the matrix resin at Tm or at T1 is less than or equal to 30%, typically less than or equal to 20%, more typically less than or equal to 10%; and
c) maintaining the temperature T1 or heating to a temperature T2 for a time sufficient for the curable composition to be cured, thereby manufacturing the composite article.
Considering the teachings of Meegan in view of Kobayashi and Ponsolle, it would have been obvious to a person having ordinary skill in the art at the time the invention was filed to select thermoplastic fiber having a melting temperature of 180 °C or less to prepare the NCF of Meegan as Meegan teaches the composition is cured at 170° C to 180° C and Ponsolle the Tm of the thermoplastic fiber is at or below the cure temperature. Regarding claim 2; Meegan teaches polyglycidyl adducts of amines, such as N,N-diglycidyl aniline, as suitable epoxy compounds [p. 0082].
Regarding claim 4 and 12; Meegan teaches the curable resin composition comprises,
from 5 to 95 pbw of the at least one halo-substituted diethyltoluenediamine,
from 5 to 95 pbw of the at least one multifunctional aromatic amine, and
from 10 to 90 pbw of the one or more epoxy compound
based on 100 pbw of the combined amount of the at least one epoxy compounds, at least one multifunctional aromatic amine, and at least one halo-substituted diethyltoluenediamine of the resin composition [p. 0090-0092].
One having ordinary skill in the art at the time the invention was filed would recognize that the general teachings of Meegan obviously embrace embodiments wherein the curing agents satisfy the claimed curing agents A-C and amounts thereof. 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 claim 5; Meegan teaches the halo-substituted diethyltoluenediamine remains liquid when maintained at temperature greater than or equal to 25° C [p. 0079]. Therefore, the halo diamine obviously has a melting temperature of 150° C or less.
Regarding claim 6; The halo-substituted diethyltoluenediamine taught by Meegan is a phenylene diamine derivative [p. 0078]. Meegan teaches examples of the multifunctional aromatic amine that are 4,4’-diaminodiphenylmethane derivatives, including MDEA, M-CDEA, M-MIPA, and M-DIPA [p. 0058-0062].
Regarding claim 10; Meegan teaches an embodiment wherein the composition comprises carbon fibers [p. 0098].
Claim(s) 3 is/are rejected under 35 U.S.C. 103 as being unpatentable over Meegan (US 2021/0403637 A1), in view of Kobayashi et al. (US 2021/0122892 A1) and Ponsolle et al (US 2024/0269957 A1), as applied to claims 1-2, 5-6, and 9-12 above, and further in view of Ozawa (US 20200407548 A1).
The disclosure of Meegan, Kobayashi and Ponsolle is above and is applied here as such.
Regarding claim 3; Meegan is silent with respect to a teaching regarding the amount of the individual epoxy components of the one or more epoxy component.
Ozawa discloses a related composition and composite comprising tetraglycidyl-3,4′-diaminodiphenyl ether (epoxy resin [A])[abstract, p. 0057, 0097]. Ozawa composites comprising [A] provide cured products with improved mechanical properties [p. 0057, 0085]. Ozawa teaches the ratio of the epoxy resin [A] with respect to the total amount of the epoxy resins in the composition is preferably from 20 to 100% by mass, more preferably from 40 to 100% by mass, further more preferably from 55 to 100% by mass. When the amount of epoxy resin [A] is less than 20% by mass, heat resistance and elastic modulus of the obtained resin cured product may decrease. As a result, various physical properties of the obtained CFRP may decrease [p. 0099].
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 Meegan wherein tetraglycidyl-3,4′-diaminodiphenyl ether comprises from 20 to 100% by mass of the total amount of the epoxy resins in the composition.
Claim(s) 7 and 8 is/are rejected under 35 U.S.C. 103 as being unpatentable over Meegan (US 2021/0403637 A1), in view of Kobayashi et al. (US 2021/0122892 A1) and Ponsolle et al (US 2024/0269957 A1), as applied to claims 1-2, 5-6, and 9-12 above, and further in view of Hondo (US 20210261744 A1).
The disclosure of Meegan, Kobayashi and Ponsolle is above and is applied here as such.
Regarding claim 7; Meegan fails to teach suitable active hydrogen/ epoxy ratios.
Hondo is directed towards a similar epoxy resin composition for a fiber-reinforced composite material [p. 0002]
Hondo teaches the ratio H/E of the total number of the active hydrogens of the amine compound contained in the curing agent (H) to the total number of the epoxy groups contained in the epoxy resin (E) is preferably 1.1 or more and 1.4 or less. H/E is more preferably 1.2 or more and 1.3 or less. In the case that H/E is 1.1 or more, a good effect of improving the curability and an effect of improving the plastic deformation ability of the epoxy resin cured product are easily obtained. In the case that H/E is 1.4 or less, high heat resistance is likely to be exhibited. [0041]
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 Meegan wherein H/E is from 1.1 to 1.4. 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 claim 8; Meegan is silent with respect to suitable particle diameters of the resin particles.
Hondo teaches it is more preferable that the epoxy resin composition for a fiber-reinforced composite material include the core-shell rubber particle including an epoxy group in the shell portion, and the core-shell rubber particle have a volume average particle diameter in the range of 50 nm or more and 300 nm or less. If the epoxy resin composition for a fiber-reinforced composite material includes the core-shell rubber particles satisfying such a condition, the core-shell rubber particles are easily dispersed particularly uniformly and well in the epoxy resin composition, and an excellent effect of improving the toughness is easily exhibited. [0047]
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 Meegan wherein the core-shell rubber particle have a volume average particle diameter in the range of 50 nm or more and 300 nm or less. 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).
Conclusion
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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