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 Interpretation
With respect to the claimed ionic liquid as recited in instant claims 1 and 4, it is noted that the specification recites that the “tetraalkyl phosphonium ion” and the “tetraalkyl ammonium ion” of the claimed “tetraalkyl phosphonium ionic liquid” and the claimed “tetraalkyl ammonium ionic liquid”, respectively, have the following structures, respectively:
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and
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, wherein R1, R2, R3, and R4 are independently hydrogen, C1-14 alkyl group, C1-3 alkylol group, phenyl group or benzyl group
(emphasis added) in Paragraphs 0019-0020 (of the specification as filed), and as also recited in instant claim 4. Hence, based upon the above cited section of the specification as well as recited in instant claim 4, the “tetraalkyl” phosphonium and ammonium ions may actually have other than four “alkyl” substituents given that as stated in Paragraph 0020 and instant claim 4, any of the R1-R4 substituent groups can be hydrogen, C1-3 alkylol group, phenyl group or benzyl group.
Similarly, given that the “trialkyl” sulfonium ion of the “trialkyl” sulfonium ionic liquid is recited as having a structure wherein R1-R3 may be as noted above, the claimed “trialkyl sulfonium ion” and ionic liquid thereof have been similarly interpreted as extending to sulfonium ions other than including three alkyl groups.
Claim Rejections - 35 USC § 102
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 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 1-6 are rejected under 35 U.S.C. 102(a)(1) and/or 102(a)(2) as being anticipated by Matsuura (WO2023/276814A1, please refer to US2024/0132714A1 as an English language translation thereof for the below cited sections). Matsuura discloses an epoxy resin composition comprising (A) an epoxy resin, preferably containing 2 or more epoxy groups with examples utilizing a compound having two epoxy groups (Paragraphs 0031-0033, 0056, 0072-0074, 0076, Examples); (B) a curing agent, such as a phenol-based curing agent (Paragraph 0035); (C) a filler; and (D) an ionic compound in which at least one of a cation or an anion is organic (Abstract), particularly an “ionic liquid” (Paragraph 0043) and preferably at least one ionic compound selected from the group consisting of compounds (D-1) to (D-16) as recited in Paragraph 0015 and utilized in the working examples (Paragraphs 0091-0106) including (D-1) 1-butyl-1-methylpyrrolidinium bis(trifluoromethylsulfonyl)imide having Structural formula d1 as shown in Paragraph 0091 (i.e., “Ionic liquid (6)” as recited in Table 1 and Example 6 of the instant specification); (D-4) trimethylpropylammonium bis(trifluoromethanesulfonyl)imide having Structural formula d4 as shown in Paragraph 0094 (i.e., “Ionic liquid (1)” of Table 1/Example 1); (D-6) methyltrioctylammonium bis(trifluoromethanesulfonyl)imide having Structural formula d6 as shown in Paragraph 0096 (e.g., similar to “Ionic liquid (1)” and “Ionic liquid (2)” with a tetraalkyl ammonium cation and a bis(C1-fluoroalkyl sulfonyl)imide anion); and (D-7) tributylmethylammonium bis(trifluoromethanesulfonyl)imide having Structural formula d7 as shown in Paragraph 0097 (i.e., “Ionic liquid (2)” of Table 1/Example 2; reading upon the claimed “ionic liquid” as recited in instant claims 1 and 4). Matsuura discloses that although the content ratio of the ionic compound with respect to the entire amount of the epoxy resin composition is not particularly limited, the content ratio is preferably from 0.0001 mass % (1 ppm) to 3.1 mass % (31,000 ppm), and more preferably 0.001 mass % to 1.2 mass % (Paragraphs 0014 and 0055), with respect to the entire composition; and more particularly with respect to 100 parts by mass of the epoxy resin containing 2 or more epoxy groups, the content of the ionic compound is preferably from 0.002 parts by mass to 11 parts by mass (encompassing the entire claimed range of 0.01 to 1.5 parts by weight as recited in instant claim 1), more preferably more than 0.8 part by mass and 11 parts by mass or less (overlapping about 50% of the claimed range, Paragraph 0056); with several working examples containing a content falling within the claimed range of 0.01-1.5 parts by weight with respect to 100 parts by weight of epoxy resin or a compound having two epoxy groups as in instant claim 1; e.g., Example 10 with 0.005 part of d1 to 29.1 parts of YDF8170 epoxy resin from Nippon Steel Chemical & Material - a bisphenol F type diglycidyl ether (BFDGE) epoxy resin having 2 epoxy groups as in instant claims 1-2; or Example 11 with 0.012 part of d1 to 29.0 parts of YDF8170; or Example 14 with 0.003 part of d6 to 29.1 parts of YDF8170 (Examples, Paragraph 0072, Table 2); with each of Examples 10, 11, and 14 also including 60 parts by mass of silicon dioxide filler to the 29.1 or 29.0 parts of epoxy resin (thus about 206 or 207 parts, respectively, of filler to 100 parts of epoxy resin as in instant claims 5-6).
Matsuura discloses that the curing agent to be used in the epoxy resin composition is not particularly limited, wherein suitable phenol-based curing agents include monomers, oligomers, and polymers each having a phenolic hydroxy group, with specific examples thereof including “a phenol novolac resin and an alkylated product or an allylated product thereof, a cresol novolac resin, a phenol aralkyl (including phenylene and biphenylene skeletons) resin, a naphthol aralkyl resin, a triphenol methane resin, and a dicyclopentadiene-type phenol resin” (Paragraphs 0034, 0038, as in instant claims 1 and 3), provided in a blending amount that is preferably such an amount that the stoichiometric equivalent ratio of curing agent equivalent/epoxy group equivalent thereof to the epoxy resin is from 0.6 to 1.5, more preferably a ratio of 0.7 to 1.2 (Paragraphs 0034-0035 and 0038); with at least one working example (Example 25) utilizing an equivalent ratio of 0.9 of a phenolic resin curing agent, MEH8005 (hydroxyl equivalent of 135 g/eq, from Meiwa Plastics Industries, Ltd., reading upon the claimed “compound having at least two phenolic hydroxyl groups” as in instant claim 1, and more particularly a phenol novolac/novolak resin as in instant claim 3) in an amount of 12.6 parts by mass of the phenolic resin curing agent to 26.2 parts by mass of the epoxy resin having 2 epoxy groups (i.e., about 48 parts of phenolic resin per 100 parts of epoxy resin) falling within the claimed content of 20-80 parts by weight as recited in instant claim 1, in combination with d6 methyltrioctylammonium bis(trifluoromethanesulfonyl)imide as the ionic compound (as in instant claims 1 and 4), and 60 parts of silicon dioxide filler (i.e., about 229 parts by weight filler to 100 parts of the epoxy resin, as in instant claims 5-6; Examples, Table 3). Hence, given the above exemplified components (A)-(D) and contents thereof as disclosed by Matsuura, particularly in light of the working examples with data points clearly falling within the claimed content ranges, the Examiner takes the position that Matsuura discloses the claimed invention with sufficient specificity to anticipate instant claims 1-6.
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.
Alternatively, claims 1-6 as well as claims 7-8 are rejected under 35 U.S.C. 103 as being unpatentable over Matsuura as applied to claims 1-6 above, and discussed further below.
The teachings of Matsuura are discussed in detail above (and incorporated herein by reference) and although the Examiner is of the position that the reference is anticipatory with respect to instant claims 1-6 as detailed above, the Examiner alternatively takes the position that the claimed invention as recited in instant claims 1-6 would have been obvious over the teachings of Matsuura given that it is prima facie obviousness to choose from a finite number of identified, predictable solutions, with a reasonable expectation of success and/or prima facie obviousness to simply substitute one known element for another to obtain predictable results (e.g., simply substitute the phenolic resin curing agent MEH8005 as used in Example 25 for the amine-based curing agent used in Examples 10, 11, or 14).
With respect to instant claims 7-8, Matsuura also teaches that the epoxy resin composition may further comprise a curing accelerator (Paragraph 0058), with all of the examples thereof as recited in Paragraph 0060 being imidazole compounds, such as 2-methylimidazole and 2-ethyl-4-methylimidazole (both having a structure as in instant claim 8) or 2-phenyl-4-methylimidazole (2P4MZ) as utilized in the examples; and although Matsuura does not specifically limit the content of the imidazole curing accelerator as recited in instant claim 7, given that Matsuura teaches a working example utilizing 0.4 parts of 2P4MZ (e3 in Example 39) to 28.1 parts of epoxy resin, or about 1.4 parts per 100 parts of epoxy resin, close to the claimed 0.01-1 parts by weight range, the Examiner takes the position that absent any clear showing of criticality and/or unexpected results, the claimed invention as recited in instant claims 7-8 would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention given that it is prima facie obviousness to choose from a finite number of identified, predictable solutions, with a reasonable expectation of success and one skilled in the art would have been motivated to utilize similar amounts or amounts on the same order of magnitude as utilized in Example 39 for any of the other exemplified imidazole compounds as a curing accelerator in any of the compositions and/or examples taught by Matsuura.
Claims 1-12 are rejected under 35 U.S.C. 103 as being unpatentable over Goto (US2011/0189432A1). Goto teaches an epoxy resin composition; a prepreg formed by impregnating the epoxy resin composition into a porous base material, preferably a glass fiber nonwoven fabric (Paragraphs 0183-0185, “reinforcing material” as in instant claim 9 that is glass fiber as in instant claim 10); a cured body or sheet formed by curing the epoxy resin composition or prepreg thereof (Paragraphs 0186-0187, as in instant claims 9-10); and a multilayer laminated plate comprising the cured sheet with a metal layer on one or both surfaces thereof, particularly a copper clad laminated plate comprising copper foils on both surfaces of the resin sheet/prepreg (as in instant claims 11-12; Entire document, particularly as noted above as well as Abstract; Paragraphs 0179-0180, 0213-0224, and 0277-0278; Claims 8-16; and Examples). Goto teaches that the epoxy resin composition comprises: (i) an epoxy resin, preferably having two or more epoxy groups in a single molecule, such as a Bisphenol A type epoxy resin (Paragraphs 0035-0041) as utilized in the examples, namely RE-310S manufactured by Nippon Kayaku Co., Ltd. (Paragraphs 0230-0231, reading upon the claimed epoxy resin as in instant claims 1-2); (ii) 1 to 200 parts by weight, with regard to 100 parts by weight of the epoxy resin, of a curing agent (Paragraph 0113) that is at least one type selected from those recited in Paragraph 0015 such as a phenol novolac resin, particularly a phenolic compound represented by formula (1), formula (2), or formula (3), and more preferably formula (7) (Paragraphs 0015, 0088-0096; reading upon the claimed compound having at least two phenolic hydroxy groups as in instant claims 1 and 3); (iii) a curing accelerator, particularly an imidazole compound as recited in Paragraph 0116, such as 2-methylimidazole or 2-ethyl-4-methylimidazole, in a content of equal to or less than 3.5 parts by weight to a total of 100 parts by weight of the epoxy resin and curing agent (Abstract, Paragraphs 0114-0118; reading upon the claimed imidazole compound as in instant claims 7-8); (iv) 10 to 400 parts by weight of a silica component obtained by performing surface treatment on silica particles, preferably 25 to 250 parts by weight with regard to 100 parts by weight of the epoxy resin and the curing agent (Abstract, Paragraph 0152; reading upon the claimed filler as recited in instant claims 5-6); and preferably (v) an organically modified sheet silicate in a content between 0.01 to 3 parts by weight of the epoxy resin and the curing agent, with an example (Example 8) utilizing a synthetic hectorite chemically treated with a trioctyl-methylammonium salt (e.g., a tetraalkyl ammonium ionic liquid as in instant claim 1), namely LUCENTITE™ STN manufactured by CO-OP Chemical Co., Ltd. (which has the organic ion in a content of 22-32wt% as evidenced by Yu, Effect of Nanoclay on Relaxation of Poly(vinylene fluoride) Nanocomposites, Abstract, Experimental) in a content of 0.27 part per 19.12 parts of epoxy resin (Table 4; thus about 0.31 to about 0.47 part of the trioctyl methylammonium salt per 100 parts of epoxy resin; Paragraphs 0154-0161 and 0240-0241; Examples).
Goto also teaches that a combination of two or more types of curing agents may be utilized in the epoxy resin composition wherein aside from the phenolic curing agent as discussed above, an ionic heat latent cationic polymerization catalyst may be utilized such as a benzylsulfonium salt, a benzylammonium salt, a benzylpyridinium salt (reading upon the claimed sulfonium, ammonium, and pyridinium cation structures of instant claim 4), “or the like” having, as a counter-anion, antimony hexafluoride, phosphorus hexafluoride (PF6- as in instant claim 4), boron tetrafluoride (BF4- as in instant claim 4), “or the like” (Paragraphs 0068 and 0082-0083; reading upon the claimed ionic liquid as recited in instant claim 1 as well as the cation(s) and anion(s) thereof as recited in instant claim 4). Hence, Goto clearly teaches an epoxy resin composition comprising all of the components as recited in instant claims 1-8 in amounts reading upon and/or rendering obvious the claimed parts by weight amounts with respect to 100 parts by weight of the epoxy resin/compound having two epoxy groups as recited in instant claims 1, 5, and 7, as well as a composite material and copper clad laminate formed therefrom as in instant claims 9-12, given that one having ordinary skill in the art before the effective filing date of the claimed invention would have been motivated to utilize any amount(s) within the ranges taught by Goto for each component of the composition for a particular end use, and given that it is prima facie obviousness to choose from a finite number of identified, predictable solutions, with a reasonable expectation of success, such that absent any clear showing of criticality and/or unexpected results of the claimed invention over the teachings of Goto, the Examiner takes the position that the claimed invention as recited in instant claims 1-12 would have been obvious over the teachings of Goto.
Claims 1-12 are rejected under 35 U.S.C. 103 as being unpatentable over Goto, as applied above, and in further view of Matsuura. The teachings of Goto are discussed in detail above and although Goto clearly teaches the use of ionic heat latent cationic polymerization catalysts or curing agents including pyridinium ionic liquids as in instant claim 1, “or the like”, in the epoxy resin composition in combination with other curing agents such as phenolic resins as discussed above, wherein Goto also teaches that the epoxy resin composition may be utilized as a sealing material, such as for semiconductor devices, as well as for prepregs, copper clad laminated plates, and printed-circuit substrates (Paragraphs 0001-0004, 0161, and 0178-0182), Goto does not specifically teach any of the other claimed ionic liquids (e.g., tetraalkyl phosphonium ionic liquid, trialkyl sulfonium ionic liquid – if meant to exclude benzyl, tetraalkyl ammonium ionic liquid – if meant to exclude benzyl, morpholinium ionic liquid, piperidinium ionic liquid, pyrrolidinium ionic liquid, thiazolium ionic liquid, triazolium ionic liquid, benzimidazolium ionic liquid, isoquinolinium ionic liquid) as recited in instant claim 1, particularly having cations and anions as recited in instant claim 4, nor does Goto limit the content of the ionic liquid as instantly claimed. However, it would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to utilize any known ionic latent catalyst or curing agent or similar ionic liquid/compound as taught by Goto that is typically utilized in epoxy resin compositions in the art such as those taught by Matsuura (discussed in detail above), reading upon the claimed ionic liquids as recited in instant claims 1 and 4. More particularly, Matsuura teaches an epoxy resin composition that may be utilized as a sealing material in a semiconductor device (Paragraphs 0002 and 0022-0025), as in Goto, wherein the epoxy resin composition preferably contains from 0.0001 mass % to 3.1 mass % of the ionic compound with respect to the entire amount of the epoxy resin composition in addition to a curing agent such as a phenolic resin curing agent as discussed above; wherein Matsuura teaches that by setting the ionic compound content within this range, “it becomes easy to more reliably suppress the bias of the distribution of the filler dispersed in the sealing material (cured product) covering the electrode connection portion” and “easy to suppress various inconveniences caused by the contamination of the vicinity of the sealing material (cured body) for the semiconductor device by the ionic compound due to the exudation of the ionic compound from the sealing material” (Paragraph 0055). Matsuura more specifically teaches that with respect to 100 parts by mass of the epoxy resin containing 2 or more epoxy groups, the content of the ionic compound is preferably from 0.002 parts by mass to 11 parts by mass (encompassing the entire claimed range of 0.01 to 1.5 parts by weight as recited in instant claim 1) with working examples falling within the claimed range as discussed in detail above (Examples). Hence, given that Matsuura and Goto are of the same field of endeavor with both teaching epoxy resin compositions comprising similar components including filler for use in similar electronic applications, the claimed invention as recited in instant claims 1-12 would have been further obvious over the teachings of Goto in view of Matsuura given that it is prima facie obviousness to simply substitute one known element for another to obtain predictable results and/or prima facie obviousness to use a known technique to improve similar devices in the same way.
Citation of pertinent prior art
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. Cheon (US2016/0159971A1) teaches an epoxy resin composition containing a phosphonium ion-containing compound as a curing catalyst in a content of about 0.01 wt% to about 10 wt%, in combination with a curing agent, such as a phenolic resin curing agent, in a content of about 0.1 wt% to about 90 wt% in terms of solid content.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to MONIQUE R JACKSON whose telephone number is (571)272-1508. The examiner can normally be reached Mondays-Thursdays from 10:00AM-5:00PM.
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/MONIQUE R JACKSON/ Primary Examiner, Art Unit 1787