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 .
The amendment filed 4/23/2026 has been entered. Claim 4 has been canceled. Claims 1-3 and 5-12 are pending in the application. 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 Rejections - 35 USC § 103
Claims 1-3 and 5-8 are rejected under 35 U.S.C. 103 as being unpatentable over Matsuura (WO2023/276814A1, please refer to US2024/0132714A1 as an English language translation thereof for the below cited sections). As discussed in the prior office action, Matsuura teaches 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 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). Matsuura more broadly teaches that “[a]s the ionic compound, for example, a pyridinium-based ionic compound, an imidazolium-based ionic compound, an ammonium-based ionic compound, a phosphonium-based ionic compound, a pyrrolidinium-based ionic compound, a piperidinium-based ionic compound, a sulfonate-based ionic compound, and an iodine-based ionic compound may be used;” and “[i]n addition, when a suitable combination of a cation and an anion is focused on, it is preferred that the ionic compound contain <i>at least one kind of cation selected from the group consisting of: a pyridinium-based cation; an imidazolium-based cation; an ammonium-based cation; a pyrrolidinium-based cation; a piperidinium-based cation; and a phosphonium-based cation, and <ii>at least one kind of anion selected from the group consisting of: a sulfonylimide-based anion; a sulfonate-based anion; a hexafluorophosphate anion; a bis(trifluoromethylsulfonyl) imide anion; an imidodisulfuryl fluoride anion; and an iodine anion” (emphasis added; Paragraph 0045), with non-limiting examples of suitable ionic compounds recited in Paragraphs 0046-0053 including, for example, 1-butyl-4-methylpyridinium bromide (Paragraph 0046), triethylmethylammonium dibutyl phosphate (Paragraph 0048), tetrabutylphosphonium methanesulfonate (Paragraph 0049), and 1-butyl-1-methylpyrrolidinium chloride (Paragraph 0050), each of which reads upon the claimed ionic liquid of instant claim 1 that consists of a cation and an anion selected from those as recited in amended claim 1, wherein the non-limiting (D-1) to (D-16) are preferred examples of the ionic compounds recited in Paragraphs 0046-0053.
Matsuura teaches 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 teaches 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, 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 contents taught by Matsuura, particularly as in the working examples, and that aside from the 16 preferred ionic compounds (D-1) to (D-16), Matsuura more broadly teaches ionic liquids reading upon the claimed ionic liquid of instant claim 1 consisting of a cation and an anion as instantly claimed, the Examiner maintains her position that the claimed invention as recited in instant claims 1-3 and 5-6 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 1-butyl-4-methylpyridinium bromide or triethylmethylammonium dibutyl phosphate or tetrabutylphosphonium methanesulfonate for any of the ionic liquids utilized in the examples, such as for the ionic liquid d6 utilized in Example 25).
With respect to instant claims 7-8, as discussed in the prior office action, 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 1-3 and 5-12 are rejected under 35 U.S.C. 103 as being unpatentable over Goto (US2011/0189432A1) and in further view of Matsuura. As discussed in the prior office action, 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, 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, “or the like” having, as a counter-anion, antimony hexafluoride, phosphorus hexafluoride, boron tetrafluoride, “or the like” (Paragraphs 0068 and 0082-0083).
Hence, with respect to the claimed invention as recited in instant claims 1-3 and 5-12, Goto teaches an epoxy resin composition generally comprising components as recited in instant claims 1-3 and 5-8, a prepreg formed by impregnating the epoxy resin composition into a glass fiber nonwoven fabric, a cured body or sheet formed by curing the epoxy resin composition or prepreg thereof, 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, e.g., as in instant claims 9-12; and although Goto clearly teaches the use of ionic heat latent cationic polymerization catalysts or curing agents including pyridinium ionic liquids “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 that the composition comprises an ionic liquid as recited in amended claim 1 consisting of the claimed cations and anions, nor does Goto limit the content of the ionic liquid as instantly claimed. However, given that Goto does not limit the ionic latent catalyst or curing agent to be utilized in the composition, 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 the ionic liquids taught by Matsuura (discussed in detail above), particularly the pyridinium-based ionic liquids recited in Paragraph 0046 such as the above noted 1-butyl-4-methylpyridinium bromide (a known cationic catalyst in the art) reading upon the claimed ionic liquids as recited in amended claim 1. 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 1-3 and 5-12 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.
Response to Arguments
Applicant's arguments filed 4/23/2026 have been fully considered but they are not persuasive and/or moot in view of the additional remarks above with respect to the obviousness rejection over Matsuura or Goto in view of Matsuura in light of the amended claims. With respect to the anticipation rejection over Matsuura, the Applicant argues that Matsuura discloses that the ionic compound consists of the cation/anion pairs as recited on pages 10-14 of the response, and that Matsuura allegedly fails to teach the ionic liquid as recited in amended claim 1, further arguing with respect to the obviousness rejection that the Office Action allegedly fails to provide any articulated reasoning with rational underpinning as to why one of ordinary skill in the art would have modified Matsuura to arrive at the specifically claimed ionic liquid as recited in amended claim 1. However, the Examiner respectfully disagrees and notes that although the ionic compounds consisting of the cation/anion pairs as recited on pages 10-14 of the response are preferred ionic compounds disclosed by Matsuura and are specifically utilized in the working examples, Matsuura does not limit the invention to these specific ionic compounds, i.e., (D-1) to (D-16) and clearly recites that the “invention is not limited only to Examples described” (Paragraph 0070), and given that Matsuura clearly teaches that ionic compounds (D-1) to (D-16) are preferred ionic compounds of those more broadly recited in Paragraphs 0043-0053, such that 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 of the ionic compounds/liquids taught by 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, Applicant’s arguments with respect to the obviousness rejection over Matsuura are not persuasive.
With respect to the obviousness rejection over Goto in view of Matsuura, the Applicant argues that in addition to the alleged deficiencies of Matsuura discussed above, Goto fails to address these deficiencies, and that the Office Action allegedly fails to provide any articulated reasoning as to why Goto would remedy the alleged deficiency of Matsuura, arguing that “Goto also fails to teach the ionic liquid as recited in amended claim 1” (see pages 14-18 of the response). However, the Examiner respectfully disagrees and first notes that the obviousness rejection was based upon Goto in view of Matsuura, not Matsuura in view of Goto as the Applicant appears to argue. It is also noted that Goto does not limit the heat latent cationic polymerization catalyst to the example compounds taught by Goto, especially given the “or the like” recitations with respect to said example compounds recited in Paragraph 0083, and hence, the Examiner maintains her position that 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 the ionic liquids taught by Matsuura like the pyridinium-based ionic liquids recited in Paragraph 0046 such as 1-butyl-4-methylpyridinium bromide, a known cationic catalyst in the art, reading upon the claimed ionic liquids as recited in amended claim 1. Hence, given the absence of any clear showing of criticality and/or unexpected results with respect to the claimed composition comprising the specific ionic liquids, Applicant’s arguments are not persuasive and the Examiner maintains her position that the claimed invention would have been obvious over the teachings of Goto in view of Matsuura for the reasons discussed in detail above given again 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.
Any objection or rejection from the prior office action not restated above has been withdrawn by the Examiner in light of Applicant’s claim amendments and arguments filed 4/23/2026.
Citation of pertinent prior art
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. Chen (WO2024/149555A1) discloses a liquid one-component (1K) epoxy resin composition and a cured product obtained therefrom, wherein the epoxy composition comprises a) from 20 to 80 wt% of at least one liquid epoxy resin, particularly a diglycidyl ether of bisphenol A; b) from 20 to 60 wt% of at least one liquid phenol resin, particularly a phenol novolac resin represented by formula (I) having two or more phenolic hydroxyl groups; and c) from 0.1 to 15 wt% of at least one phosphonium-based ionic liquid, such as diethylphosphate tributyl (ethyl phosphonium) as utilized in the examples, with a specific example comprising 59 wt% of JER 828 epoxy resin available from Mitsubishi Chemical (e.g., 100 parts by weight of a compound having two epoxy groups), 40 wt% of MEH 8000H phenol novolac resin available from UBE Corporation (e.g., ~67.8 parts by weight of a compound having at least two phenolic hydroxy groups with respect to 100 parts of the epoxy resin), and 1.0 wt% of CYPHOS IL 169 tributyl (ethyl phosphonium) diethylphosphate available from Solvay as the phosphonium-based ionic liquid (e.g., ~ 1.69 parts by weight of ionic liquid with respect to 100 parts of the epoxy resin).
THIS ACTION IS MADE FINAL. 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 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
Prosecution Insights