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 response of the applicant has been read and given careful consideration. Rejection of the previous office action not rejected below are withdrawn based upon the arguments and amendment of the applicant. Responses to the arguments of the applicant are presented after the first rejection they are directed to.
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.
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.
Claims 1,2,4-9 and 11 are rejected under 35 U.S.C. 103 as being unpatentable over Nakao et al. JP 2022051490
Nakao et al. JP 2022051490 (machine translation attached) exemplifies the following photoacid generators on pages 35-36.
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Composition 23 includes 50 parts celoxide 2021P (3,4-epoxycyclohexylmethyl (3,4-epoxy) cyclohexanecarboxylate), 50 parts TEPIC-VL (triglycidyl isocyanurate), 0.5 parts sulfonium salt AG-7 (see above), 0.5 parts BYK-UV3510 (antioxidant), 0.5 parts irganox 1010 (Irganox 1010: (Pentaerythritol Tetrakis [3- (3,5-di-t-butyl-4-hydroxyphenyl) propionate], manufactured by BASF, Inc) (see table 2 and associated text). Example 30 and 38 are similar. Example 45 includes 6 parts Celoxide 2021P, 6 parts JER157S70 (Novolak type solid epoxy resin), 24 parts Techmore VG3101L (2- [4- (2,3-epoxypropoxy) phenyl] -2- [4- [1,1-bis [4- [2,3-epoxypropoxy] phenyl] ethyl] phenyl] propane), 2 parts Epogoose PT (Polytetramethylene glycol diglycidyl ether), 5 parts OXT-101 (3-ethyl-3-hydroxymethyloxetane) 12 parts OXT221 (3-ethyl-3 {[(3-ethyloxetane-3-yl) methoxy] methyl} oxetane), 20 parts Dipentaerythritol polyacrylate, 16 parts Polypropylene glycol monoacrylate, 1.0 parts AG-8, 0.3 parts irgacure 184 (see table 3), Example 52 is similar (see table 3 and associated text) [0262-0264]. The composition was coated on a silicon wafer, exposed using UV, post exposure baked and developed in gamma-butyrolactone and washed with water [0265-0269]. Useful substrates include silicon wafers, metal substrates, polymer films, and glass substrates. Examples of the metal substrate include a stainless steel plate such as SUS. Specific examples of the polymer film include polyethylene terephthalate (PET) film, polyethylene naphthalate film, and polyimide film. The thickness is usually set within the range of 10 μm to 3 mm [0150]. The addition of a silane coupling agent is disclosed [0183-0187]. The sulfonium salts are embraced by the formula 1,
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R .sup.1 and R .sup.2 independently represent an aryl group having 10 to 14 carbon atoms or a heterocyclic hydrocarbon group having 6 to 14 carbon atoms. Examples of the aryl group having 10 to 14 carbon atoms in R .sup.1 and R .sup.2 include biphenylyl, fluorenyl, benzophenonyl, fluorenonyl, naphthyl, anthracenyl, anthracynyl and the like. Examples of the heterocyclic hydrocarbon group having 6 to 14 carbon atoms in R .sup.1 and R .sup.2 include benzofuranyl, isobenzofuranyl, benzothienyl, isobenzothienyl, xanthenyl, thiantrenyl, phenoxadinyl, phenoxatinyl, chromanyl and isochromanyl. Examples thereof include coumarinyl, dibenzothienyl, xanthonyl, thioxanthonyl, dibenzofuranyl and the like. A part of the hydrogen atom of the aryl group of R .sup.1 and R .sup.2 may be substituted with a substituent (t), and the substituent (t) may be an alkyl group having 1 to 8 carbon atoms or 6 to 6 carbon atoms. It is an aryl group of 10.Among the substituents (t), the alkyl group having 1 to 8 carbon atoms includes a linear alkyl group (methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-octyl, etc.) and a branched alkyl group (n-octyl, etc.). Examples thereof include isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl, tert-pentyl, isohexyl and isooctadecyl, etc.), cycloalkyl groups (cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.) and the like. Among the substituents (t), examples of the aryl group having 6 to 10 carbon atoms include phenyl, trill, dimethylphenyl and naphthyl. R .sup.1 and R .sup.2 may be the same or different, but they are preferably the same. In the formula (1), R .sup.3 and R .sup.4 independently represent an alkyl group having 1 to 8 carbon atoms, and the definition thereof is synonymous with the alkyl group having 1 to 8 carbon atoms in the substituent (t). R .sup.3 and R .sup.4 may be the same or different, or may be partially different. m1 represents the number of R3 and is an integer of 0 to .sup.4 , preferably 0 to 2. m2 represents the number of .sup.R4 and is an integer of 0 to 5, preferably 0 to 2. When m1 or m2 is an integer of .sup.2 or more, the corresponding plurality of R3 or .sup.R4 may be the same or different. L represents a sulfur atom, that is, a group represented by —S—. X .sup.- is not limited as long as it is a monovalent polyatomic anion, and corresponds to an acid (HX) generated by irradiating a sulfonium salt with active energy rays (visible light, ultraviolet rays, electron beams, X-rays, etc.). Although it is an anion, MY .sub.a- .sup., (Rf) .sub.b PF .sub.6-b- .sup., R .sup.5 .sub.c BY .sub.4-c- .sup., R .sup.5 .sub.c GaY .sub.4-c- .sup., R .sup.6 SO .sub.3- .sup., (R .sup.6 SO .sub.2 ) .sub.3 Anions represented by C- .sup.or .sup.( R .sup.6 SO .sub.2 ) .sub.2 N- are preferred. M represents a phosphorus atom, a boron atom or an antimony atom. Y represents a halogen atom (preferably a fluorine atom). Rf represents an alkyl group in which 80 mol% or more of a hydrogen atom is substituted with a fluorine atom (an alkyl group having 1 to 8 carbon atoms is preferable). Alkyl groups to be Rf by fluorine substitution include linear alkyl groups (methyl, ethyl, propyl, butyl, pentyl, octyl, etc.), branched chain alkyl groups (isopropyl, isobutyl, sec-butyl, tert-butyl, etc.) and cyclo. Examples thereof include alkyl groups (cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.). The ratio of hydrogen atoms of these alkyl groups substituted with fluorine atoms in Rf is preferably 80 mol% or more, more preferably 90, based on the number of moles of hydrogen atoms possessed by the original alkyl group. % Or more, particularly preferably 100%. When the substitution ratio by the fluorine atom is in these preferable ranges, the photosensitivity of the sulfonium salt is further improved. Particularly preferred Rf are CF .sub.3- , CF .sub.3 CF .sub.2- , (CF .sub.3 ) .sub.2 CF-, CF .sub.3 CF .sub.2 CF .sub.2- , CF .sub.3 CF .sub.2 CF .sub.2 CF .sub.2- , (CF .sub.3 ) .sub.2 CFCF .sub.2- , CF .sub.3 CF .sub.2 (CF .sub.3 ) CF- and (CF .sub.3 ) .sub.3 C-. The b Rfs are independent of each other and therefore may be the same or different from each other [0008-0038]. Examples of the aromatic epoxide include polyglycidyl ether and polyglycidyl ester of polyhydric phenol or an alkylene oxide adduct thereof. Specific examples thereof include bisphenol A, bisphenol E, bisphenol F, bisphenol AD, and bisphenol. Z or glycidyl ether, phenylglycidyl ether, tert-butylphenyl glycidyl ether, resorcinol diglycidyl ether, tetraphenol ethane tetraglycidyl ether, triphenol methane, which are compounds in which alkylene oxides such as ethylene oxide and propylene oxide are further added. Triglycidyl ether, glycidylated product of condensate of phenols or naphthols and aldehydes (eg phenol resin or novolak resin), glycidylated product of condensate of phenols and isopropenyl acetophenone, reaction of phenols with dicyclopentadiene Examples thereof include a noglycidyl compound, a diglycidyl ester of terephthalic acid, a diglycidyl ester of isophthalic acid, and a diglycidyl ester of o-phthalic acid [0068]. Typical compounds include, for example, butyl glycidyl ether, 2-ethylhexyl glycidyl ether, higher alcohol glycidyl ether, alkylenediol diglycidyl ether (eg, 1,4-butanediol diglycidyl ether, 1,6-hexane). Diglycidyl ether of diol, diglycidyl ether of neopentyl glycol, etc.), triglycidyl ether of glycerin, diglycidyl ether of trimethylolpropane, triglycidyl ether of trimethylolpropane, tetraglycidyl ether of sorbitol, hexaglycidyl of dipentaerythritol Examples thereof include glycidyl ethers of polyhydric alcohols such as ethers, diglycidyl ethers of polyethylene glycol, diglycidyl ethers of polypropylene glycol, and diglycidyl ethers of polytetramethylene glycol [0070]
Nakao et al. JP 2022051490 does not exemplify composition meeting the claims which include a borate anion as part of the sulfonium salt, use the full range of benzoyl phenyl sulfonium salts bounded by formula (1), the full range of novolak resins disclosed, use the full range of the triepoxy compound/monomers disclosed or which use a silane coupling agent.
With respect to claims 1,2,4-6,8,9 and 11, it would have been obvious to one skilled in the art to modify the compositions of examples 45 or 52 by replacing at least a portion of photoacid generator AG-7 with other benzoyl containing sulfonium salts bounded by formula (1) at [0008-0038] or exemplified on pages 35-36 modified by having a borate anion/counterion based upon the equivalence established at [0036] with a reasonable expectation of forming a useful negative acting curable composition.
With respect to claims 1,2,4-9 and 11, it would have been obvious to one skilled in the art to modify the compositions of examples 45 or 52 by replacing at least a portion of photoacid generator AG-7 with other benzoyl containing sulfonium salts bounded by formula (1) at [0008-0038] or exemplified on pages 35-36, and having a borate anion/counterion based upon the equivalence established at [0036] and adding a silane coupling agents to improve adhesion as taught at [0183-0187] with a reasonable expectation of forming a useful negative acting curable composition.
With respect to claims 1,2,4-6,8,9 and 11, it would have been obvious to one skilled in the art to modify the compositions of examples 45 or 52 by replacing at least a portion of photoacid generator AG-7 with other benzoyl containing sulfonium salts bounded by formula (1) at [0008-0038] or exemplified on pages 35-36, and having a borate anion/counterion based upon the equivalence established at [0036] and at least a portion of the JER157S70 with other novolak epoxy resins such as those disclosed at [0068] with a reasonable expectation of forming a useful negative acting curable composition.
With respect to claims 1,2,4-6,8,9 and 11, it would have been obvious to one skilled in the art to modify the compositions of examples 45 or 52 by replacing at least a portion of photoacid generator AG-7 with the same sulfonium cation and a different borate anion/counterion based upon the equivalence established at [0036] with a reasonable expectation of forming a useful negative acting curable composition.
The combination of these bases is also considered obvious
In the response of 4/15/2026, the applicant argues that Nakao et al. JP 2022051490 does not teach the borate as the counterion of the recited sulfonium salt. This is incorrect. Nakao et al. JP 2022051490 does not exemplify a specific compound including the recited benzoylphenyl containing sulfonium cation and a borate anion. As pointed out by the examiner Nakao et al. JP 2022051490 does teach borate counterions at [0036,0037,0041,0044,0046,0051]. The applicant argues that the extensive list of anions does not allow one to choose the borate. The examiner disagrees, pointing out that at [0041], M can be phosphorous, boron or antimony and at [0036], describes anions containing phophorous, boron, gallium, alkylsulfonate, alkyltrisulfonates (
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) and nitrogen containing disulfonates (
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), so the choice of anions is between three or perhaps six groups. The examiner has identified examples which are closer to the claimed composition than the comparative examples of the instant application. The applicant is invited to show unobvious results which can be attributed to the use of the benzoylphenyl containing sulfonium cation and a borate anion and amend the claims as necessary to render the showing commensurate in scope with the coverage sought., such as specific borate anions and mass% amounts of the recited sulfonium salt and the epoxides. The rejection stands.
Claims 1,2 and 4-11 are rejected under 35 U.S.C. 103 as being unpatentable over Nakao et al. JP 2022051490, in view of Iwashita et al. JP 2020042223.
Iwashita et al. JP 2020042223 (machine translation attached) exemplifies in example 6, 10 and 11, 100 parts of a cresol novolak TR4020G), 70 parts trimethylolpropane triglycidyl ether (EX-321L, B-1), a polyfunctional bisphenol A novolak resin (JER157S70, B-2), a sulfonium salt (triarylsulfonium tetrakis (pentafluorophenyl)borate, C-2; sulfonium gallates (C-3, C-4), methyl ethyl ketone (solvent) and 3-glycidoxypropyltrimethoxysilane (silane coupling agent) [0123-0125]. The compositions are coasted on a PET support and dried, the photosensitive layer was then laminated onto a silicon wafer, the PET layer peeled, the composition exposed, post exposure baked and developed in PGMEA [0126-0133]. A protective layer for covering the photosensitive layer may be further provided on the photosensitive layer [0093-0095].
Nakao et al. JP 2022051490 does not teach the application of a protective layer to the photosensitive film.
It would have been obvious to one skilled int her art to modify the process of Nakao et al. JP 2022051490 by initially coating compositions rendered obvious by Nakao et al. JP 2022051490 as discussed above on a polymeric PET substrate as taught at [0150] of Nakao et al. JP 2022051490 and [0126-0133] of Iwashita et al. JP 2020042223 and providing a protective cover layer over the photosensitive layer to protect it as taught at [0093-0095] of Iwashita et al. JP 2020042223 with a reasonable expectation of forming a useful photosensitive laminate, which can be stored and later laminated onto the final substrate to be patterned.
The examiner relies upon the response above as no further arguments were directed at this rejection.
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
Iwashita et al. JP 2020042222 (machine translation attached) teaches the equivalence of gallium and borate anions in onium salt photoacid generators (see abstract)
Ikeda et al. WO 2014061062 (machine translation attached) in examples 8 synthesizes [4- (4-benzoyl) phenylthio] phenyl diphenylsulfonium tetrakis (hexafluorophenyl) borate (P2-BP) [0206-0207].
Suzuki et al. JP 2011195499 (machine translation attached) in examples 3 teaches the synthesis of 4-benzoylphenyl- [4- (4-benzoylphenylthio) phenyl] phenylsulfonium tetrakis (pentafluorophenyl) borate (5) [0225]. Example 11 teaches the synthesis of Synthesis of 4-benzoylphenyl- [4- (3-bromo-4-benzoylphenylthio) phenyl] phenylsulfonium tetrakis (pentafluorophenyl) borate (13) [0235].
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 Martin J Angebranndt whose telephone number is (571)272-1378. The examiner can normally be reached 7-3:30 pm EST.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Mark F Huff can be reached at 571-272-1385. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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MARTIN J. ANGEBRANNDT
Primary Examiner
Art Unit 1737
/MARTIN J ANGEBRANNDT/Primary Examiner, Art Unit 1737 April 30, 2026
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