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 .
Claim Objections
Claims 1-6, 10-12, and 16 are objected to because of the following reasons:
With respect to claim 1, part (ii), the use both “at least one” and “combinations thereof” is redundant.
With respect to claim 2, the use both “at least one” and “combinations thereof” is redundant.
With respect to claim 3, the term “the second functional group” is inconsistent with previous recitation “at least one second functional group” and should therefore read as “the at least one second functional group.”
With respect to claims 3-6, the term “the component (A)” is inconsistent with previous recitation “reactive component (A)” and should therefore read as “the reactive component (A).”
With respect to claim 4, the term “the functional group” is inconsistent with previous recitation “two or more first functional groups” and should therefore read as “the two or more first functional groups.”
With respect to claims 10-12, the term “the co-monomer” is inconsistent with previous recitation “at least one co-monomer” and should therefore read as “the at least one co-monomer.”
With respect to claim 16, the term “the resin composition” is inconsistent with previous recitation “thermosetting resin composition” and should therefore read as “the thermosetting resin composition.”
Appropriate correction is required.
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.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claims 1, 2, 5, 6, 9-12, 14, 16, and 17 are rejected under 35 U.S.C. 102(a)(1 or 2) as being anticipated by Miyata (WO 2020/0217706, machine translation)
With respect to claims 1, 2, 5, 16, and 17, Miyata discloses a resin composition for fiber-reinforced composite material and prepreg and fiber-reinforced composite material obtained therefrom comprising reinforcing fibers and maleimide resin, an alkenylphenol resin, and a thiol compound as thermosetting resin components (i.e., not epoxy) (abstract). The resin is impregnated into the reinforcing fibers (paragraph 0118). Miyata teaches that carbon fibers are preferably treated with a sizing agent in order to improve mechanical strength and that the sizing agent is reactive with thiol groups of the resin (paragraphs 0107-0108). The sizing agent can be bisphenol A diglycidyl ether type epoxy resins (i.e., a compound with at least two epoxy groups and an aromatic functional group) and includes epoxy, vinyl, (meth)acrylic groups, and isocyanate (paragraph 0108). Miyata teaches that the fiber-reinforced composition has a glass transition temperature of at least 210°C, most preferably at least 250°C (paragraph 0122).
With respect to claim 6, bisphenol A diglycidyl ether has a molecular weight around 340 g/mol.
With respect to claims 9-12, the thermosetting resin is derived from an allyl compound having at least two allyl groups and at least one benzene ring (reads on claimed co-monomer (C) having a vinyl group), a maleimide compound having at least two maleimide groups (reads on claimed maleimide compound (B-1)), and a thiol compound having at least two thiol groups (reads on claimed co-monomer (C) when a thiol group) (abstract).
With respect to claim 14, Example 2 in Table 1 (original WO document, paragraph 0135) includes 232 parts by weight (pbw) maleimide having molecular weight 358.35, 100 pbw diallyl compound having molecular weight 308.41, and 34 pbw thiol compound having molecular weight of 525.62. From the parts by weight and molecular weight, the mole ratio of maleimide to co-monomers is about 1.7.
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 of this title, 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 13 and 15 are rejected under 35 U.S.C. 103 as being unpatentable over Miyata (WO 2020/0217706, machine translation) .
The discussion with respect to Miyata in paragraph 3 above is incorporated here by reference.
With respect to claim 13, the thermosetting resin is derived from 100 parts by weight of allyl compound having at least two allyl groups and at least one benzene ring (reads on claimed co-monomer (C) having a vinyl group), 155-530 parts by weight maleimide compound having at least two maleimide groups (reads on claimed maleimide compound (B-1)), and 15-120 parts by weight of thiol compound having at least two thiol groups (reads on claimed co-monomer (C) when a thiol group) (abstract). Example 2 in Table 1 (original WO document, paragraph 0135) includes 232 parts by weight (pbw) maleimide having molecular weight 358.35, 100 pbw diallyl compound having molecular weight 308.41, and 34 pbw thiol compound having molecular weight of 525.62. From the parts by weight and molecular weight, the mole ratio of maleimide to co-monomers is about 1.7 which is outside claimed range of less than 0.5.
Nevertheless, Miyata teaches that the relative amounts determine desirable heat resistance and mechanical strength (paragraphs 0026-0027). Exemplified thermosetting resins are derived from 2,2’-diallylbisphenol, 4,4’-diphenylmethane bismaleimide, and tris-[(3-mercaptopropionyloxy)-ethyl]isocyanurate (paragraph 0128).
Given that Miyata discloses a range of suitable amounts and states that the relative amounts of comonomers can be optimized to obtain desired combination of properties, it would have been obvious to one of ordinary skill in the art to utilize relatively less maleimide compound (but still within disclosed at 155 pbw or above) and thereby arrive at a lower molar ratio.
With respect to claim 15, Miyata discloses other thermosetting resins can be used such as benzoxazine resin (paragraph 0102). Therefore, it would have been obvious to one of ordinary skill in the art to utilize a benzoxazine resin to prepare Miyata’s prepreg. Case law holds that the selection of a known material based on its suitability for its intended use supports prima facie obviousness. Sinclair & Carroll Co vs. Interchemical Corp., 325 US 327, 65 USPQ 297 (1045).
Claims 3, 4, 7, 8, and 18-20 are rejected under 35 U.S.C. 103 as being unpatentable over Miyata (WO 2020/0217706, machine translation) in view of Nakayama (US 10,184,034).
The discussion with respect to Miyata in paragraph 3 above is incorporated here by reference.
With respect to claims 3 and 4, Miyata teaches that the sizing agent can have an isocyanate group (paragraph 0108) but fails to disclose a urethane group or to explicitly teach three or more of the first functional groups.
Nakayama discloses a carbon fiber-reinforced composite comprising carbon fibers that are sized with a compound having two or more epoxy groups or two or more other functional groups and a tertiary amine compound (abstract). Nakayama teaches that treating carbon fiber with epoxy compound and tertiary amine provides for significantly excellent adhesion between carbon fiber to matrix resin (col. 9, lines 34-49). Nakayama preferably treats carbon fiber with three or more epoxy groups and a second functional group such as urethane in order to improve adhesion (col. 11, line 57 to col. 12, line 20). Nakayama teaches that the thermosetting resin impregnated into the carbon fibers includes bismaleimide resin (col. 69, lines 14-18), like Miyata’s thermosetting resin.
Given that Miyata is open to sizing agents for its carbon fibers and further given that Nakayama teaches that a particularly advantageous sizing agent is with at least 3 epoxy groups and a second functional group that is urethane, it would have been obvious to one of ordinary skill in the art to prepare a prepreg with carbon fibers treated with a compound having at least 3 epoxy groups and a urethane functional group.
With respect to claim 7, Nakayama’s the tertiary amine compound serves as an accelerator in the sizing agent (col. 4, lines 59-62).
With respect to claim 8, Nakayama teaches that the carbon fibers preferably have a surface oxygen concentration of 0.05-0.50 in order to achieve strong adhesion (col. 41, lines 18-36).
With respect to claims 18-20, Miyata teaches that the sizing agent improves interfacial adhesion (paragraphs 0107 and 0108). Also, because Miyat that the fiber-reinforced bismaleimide composite has a Tg of preferably greater than 250°C, the fiber-reinforced composite would be expected to exhibit about the same properties at room temperature at elevated temperature such as at 232°C (RTA vs TOS).
Nakayama teaches that its sizing agent provides “excellent” interfacial adhesion between carbon fibers and matrix resin (col. 9, lines 45-49) when compared to prior art’s carbon fiber surface treatments. Nakayama teaches that annealing the carbon fibers improves the adhesion even further (col. 10, lines 54-67). Nakayama discloses improving interlaminar shear strength and even a method of measuring interlaminar shear strength (col. 78, line 61 to col. 79, line 8) but does not give specific values of interlaminar shear strength.
Neither teaches interlaminar shear strength RTA (tested at room temperature) or TOS (tested at 232°C).
Even so, given that Miyata discloses a fiber-reinforced composite with a Tg of at least 250°C and further given that both Miyata and Nakayama clearly disclose significantly improving interfacial adhesion between glass fibers and impregnated thermosetting resin, it would have been obvious to one of ordinary skill in the art to optimize the adhesion with a sizing agent and thereby obtain the claimed interlaminar shear strength RTA and TOS.
Conclusion
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/Vickey Nerangis/
Primary Examiner, Art Unit 1763
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