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 Rejection of the previous action not repeated below are withdrawn based upon the amendment and arguments of the applicant. Response 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 16,19-21 and 28 are rejected under 35 U.S.C. 102(a)(1) as being fully anticipated by Kropp et al. 20070219285.
Kropp et al. 20070219285 in example 2 includes 69 parts phenoxyethyl acrylate (PEA), 23 parts of SAX35 (alkoxy terminated polyether), 0.9 parts Darocure 1173 (2-Hydroxy-2-methyl- propiophenone) and 2.6 parts of a mixture of diaryliodonium tetra(pentafluorophenyl)borate (Rhodasil 2074), isopropylthioxanthone (ITX) (catalyst 2) and 4.6 parts of silicone treated silica (Aerosil R202) (see table 2 on page 6). Examples 1,3 and 4 are similar. These are cured using UV radiation [0054]
Based solely upon the 69 parts phenoxyethyl acrylate (PEA), 0.9 parts Darocure 1173 (2-Hydroxy-2-methyl- propiophenone) and 2.6 parts of a mixture of diaryliodonium tetra(pentafluorophenyl)borate (Rhodasil 2074), isopropylthioxanthone (ITX, sensitizing dye) (catalyst 2), the monomer is used in an amount of 95.2 wt%, the photoinitiator is used in an amount of 1.2 wt% and the coinitiator (catalysts 2, diaryliodonium tetra(pentafluorophenyl)borate and isopropylthioxanthone) is used in amounts of 6.3 wt%.
Claims 16,17,19-22,26 and 28 are rejected under 35 U.S.C. 103 as being unpatentable over Kondo et al. JP-H09109352.
Kondo et al. JP-H09109352 (machine translation attached) in examples 6 teaches a PVC film coated with a UV curable ink, including a 100 parts of photocurable reins, 50 parts of kayaacryl red, 2 parts of tetrabutylammonium butyltrinaphthyl borate and 2 parts of Darocure 1173 in 400 parts acetone. , The was used using UV through a photomask [0085-0087]. Example 2 coated on a substrate a photosensitive composition of Trimethylolpropane triacrylate 100 parts by weight NE1110 (manufactured by Mitsui Toatsu Co., Ltd.) 150 parts by weight Red pigment Red B (manufactured by Nippon Kayaku Co., Ltd.) 10 parts by weight Dye: 2- [2- [2- (Diphenylamino) -3-[[3- (4-methoxy-4-oxobutyl) naphtho [2,3-d] thiazol-2 (3H) -ylidene] ethylidene] -1-cyclopenten-1-yl] ethenyl] -3- (4-methoxy-4-oxobutyl) -naphtho [2,3-d] thiazolium butyltriphenylborate 3 parts by weight tetrabutylammoniumbutyltrinaphthylborate 3 parts by weight 2,4,6-2,2'- Bis (o-chlorophenyl) -4,4 ', 5,5'-tetraphenyl-1,2'-bisimidazole 4 parts by weight Acetone 500. This was exposed using semiconductor laser [0066-0070]. Example 4 coated on a substrate as composition including Dipentaerythritol hexaacrylate 50 parts by weight UA306H (manufactured by Kyoeisha Chemical Co., Ltd.) 25 parts by weight 4EG (manufactured by Kyoeisha Chemical Co., Ltd.) 25 parts by weight SE01 (manufactured by Toyobo Co., Ltd.) 100 parts by weight Tachylol 130-G (Sumitomo) Chemical Co., Ltd.) 5 parts by weight 1-ethyl-4- [7- (1-ethyl-4-quinolinylidene) -1,3,5-heptatrienyl] quinolinium iodide 0.5 parts by weight N-ethylpyridinium tetrabenzylborate 1 Parts by weight triphenylsulfonium triflate 1 part by weight talc (Japan talc) 20 parts by weight tetrahydrofuran 200 parts by weight. This was exposed through a photomask to infrared radiation from an LED [0076-0080]. The dye that can be used in the photosensitive layer of the image forming material is an organic dye having an absorption maximum in the visible to near infrared region. Representative examples of these are merocyanine dyes, xanthene dyes, thioxanthene dyes, indigo dyes, aromatic amine dyes, phthalocyanine dyes, oxazine dyes, thiazine dyes, azo dyes, quinone dyes, azomethine dyes, cyanine dyes, diallylmethane. Examples thereof include dyes, triallylmethane dyes, pyrylium dyes and squarylium dyes. If the dye has a counter anion, the anion, chloride ion as a halide ion, bromide ion, iodide ion, fluoride ion; .sub..sup..sub..sup.perchlorate; PF 6 -; BF 4 - ; SbF 6 .sup..sub..sup..sub.-; HSO 4 -; CH 3 SO 3 as aliphatic sulfonic acid ion .sup.-, FCH .sub.2 SO .sub.3 .sup.-,Dodecyl sulfate ion; trifluoroacetic acid; benzenesulfonate ion, tosylate ion as aromatic sulfonate ion, dodecylbenzenesulfonate ion, naphthalenesulfonate ion; dinitrophenolate ion, picrate ion as phenolate ion; quaternary As boron ions, methyltriphenylboron ion, butyltriphenylboron ion, dodecyltriphenylboron ion, benzyltriphenylboron ion, triphenylsilyltriphenylboron ion, methyltri (t-butylphenyl) boron ion, butyltri (t-Butylphenyl) boron ion, dodecyltri (t-Butylphenyl) boron ion, benzyltri (t-butylphenyl) boron ion, butyltritolylboron ion, butyltri (dimethylphenyl) boron ion, butyltri (trimethylphenyl) boron ion, Butyltrinaphthylboron ion, butyltri (ethoxyphenyl) boron ion, butyltrianisylboron ion, butyltri (phenoxyphenyl) boron ion, dibutyldiphenylboron ion, tetrabutylboron ion, tetraphenylboron ion, tetra (t-Butylphenyl) boron ion, tetra (trimethylphenyl) boron ion, tetratolylboron ion, Tetrabenzylboron ion is mentioned. Of these, examples of particularly preferable dyes include those shown in Tables 1 and 2 of Japanese Patent Application No. 5-275628. The wavelength from the visible region to the near-infrared region mentioned here means a region of 400 nm to 2000 nm [0018-0020].
The polymerization aid which is a quaternary boron ion complex is
General formula (1); Z .sup.+ .Math. B .sup.− R .sub.1 R .sub.2 R .sub.3 R .sub.4 (wherein Z .sup.+
Represents a cation, and R .sub.1 , R .sub.2 , R .sub.3 , and R .sub.4 are each independently an alkyl group, an aryl group, an allyl group, Aralkyl group, alkenyl group, alkynyl group, silyl group, heterocyclic group, substituted alkyl group, substituted aryl group, substituted allyl group, substituted aralkyl group, substituted alkenyl group, substituted alkynyl group, or substituted silyl group) , R .sub.1 , R .sub.2 , R .sub.3 , and R .sub.4 are each independently a phenyl group, a butylphenyl group, a toluyl group, an ethylphenyl group, an anisyl group, an ethoxy group, a phenoxy group, a chlorophenyl group, a fluorophenyl group, a xylyl group. , Mesityl group, methyl group, butyl group, octyl group, dodecyl group, cyclohexyl group, cyclohexenyl group, methoxymethyl group, phenoxymethyl group, vinyl group, allyl group, triphenylsilyl group, trimethylsilyl group, piperidyl group, thienyl group, A furyl group or the like is preferable, and Z .sup.+ is a quaternary ammonium cation, a quaternary pyridinium cation, or 4 Quinolinium cation, tertiary sulfonium cation, Iodonium cation, phosphonium cation, merocyanine dye cation, xanthene dye cation, thioxanthene dye cation, aromatic amine dye cation, oxazine dye cation, thiazine dye cation, azo dye cation, quinone dye cation , Azomethine dye cation, cyanine dye cation, diallylmethane dye cation triallylmethane dye cation, pyrimlim dye cation, squarylium dye cation.
Quaternary boron ion (B .sup.-- R .sub.1 R .sub.2 R .sub.3 R
Examples of .sub.4 ) include methyltriphenylboron ion, Butyltriphenylboron ion, dodecyltriphenylboron ion, benzyltriphenylboron ion, Examples thereof include triphenylsilyltriphenylboron ion, methyltri (t-butylphenyl) boron ion, butyltri (t-butylphenyl) boron ion, and tetrabenzylboron ion. Specific examples of the cation (Z .sup.+ ) include tetramethylammonium, tetrabutylammonium, tetradodecylammonium, trimethylhydrogenammonium, tributylhydrogenammonium, tridotecilhydrogenammonium, pyridinium, Methylpyridinium, dodecylpyridinium, quinolium, methylquinolium, dodecylquinolium, tetramethylphosphonium, tetradodecylphosphonium, tetraphenylphosphonium, diphenylsulfonium, triphenylsulfonium, diphenyliodonium, alkali metal ions, alkaline earth metal ions, cations Transition metal complex ion, and Japanese Patent Application No. 5-27562 The cation part of the ionic dyes shown in Tables 1 and 2 of Table 8 can be mentioned. In the present invention, the amount of the dye and the polymerization agent is 0.001 to 2 per 100 parts by weight of the polymerizable compound [0022-0029].
Examples of the photopolymerization accelerator include organic peroxides, bisimidazoles, sulfonium salts, triazines, iodonium salts, organic acids, sulfonic acid esters, N-acetylimides, acetophenone photopolymerization initiators, and benzoin photopolymerizations. An initiator, a thioxanthone photopolymerization initiator, and a benzophenone photopolymerization initiator are preferably used. Specifically, 2,4,6-tris (trichloromethyl)-1,3,5-triazine, triphenylsulfonium salt, diphenyliodonium salt, 2,2'-bis (o-Chlorophenyl) -4,4 ', 5,5'-tetraphenyl-1,2'-bisimidazole, 1,2-naphthoquinonediazo-5-sulfonate, pt-butylcatechol, pyrogallol, t-butylper Oxybenzoate, 3,3 ′, 4,4′-tetrakis (t-butyldioxycarbonyl) benzophenone, 2,5-dimethyl-2,5-di (benzoylperoxy) hexane, N-Acetylphthalimide, diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropane-1-one (darocure 1173), 1-hydroxycyclohexyl phenyl ketone, benzoin, benzoin ethyl ether, benzyl dimethyl ketal, benzophenone, thioxanthone, Acylphosphine oxide, 4,4′-dimethylaminobenzophenone, and ethyl 4-dimethylbenzoate are added in an amount of 20 parts by weight or less, preferably 0.0001 to 10 parts by weight, based on 100 parts by weight of the polymerizable compound. Can be used [0030].
Kondo et al. JP-H09109352 does not exemplify a composition including a sensitizing dye, a borate compound and 2-hydroxy-2-methyl-1-phenylpropane-1-one (darocure 1173)
It would have been obvious to one skilled in the art to modify example 4 by replacing the
triphenylsulfonium triflate with the same amounts of 2-hydroxy-2-methyl-1-phenylpropane-1-one (darocure 1173) based upon their equivalence at [0030] with a reasonable expectation of forming a useful photosensitive composition. Considering only the 50 parts Dipentaerythritol hexaacrylate (88 wt%), 5 parts by weight Dye 1-ethyl-4- [7- (1-ethyl-4-quinolinylidene) -1,3,5-heptatrienyl] quinolinium iodide (5.7 wt%), 0.5 parts by weight N-ethylpyridinium tetrabenzylborate (0.6 wt%) and 1 parts by weight of 2-hydroxy-2-methyl-1-phenylpropane-1-one (darocure 1173) (1.1 wt%) in the resultant composition.
Further it would have been obvious to modify the resultant composition by replacing the quaternary ammonium borate salt with others bounded by the teachings including those with tetramethylammonium or tetrabutylammonium cations and tetrahexylboron or hexyltriphenylboron anions based upon the teachings at [0022-0029] with a reasonable expectation of forming a useful photosensitive composition.
Claims 16,19-23 and 25-28 are rejected under 35 U.S.C. 103 as being unpatentable over Fujii et al. JP 2013182040
Fujii et al. JP 2013182040 (machine translation attached) teaches in composition 1, 1.0 g of a catiopnically curable monomer, 1.6 g of a binder, 1.0 g of 9,9- bis [4 (2-acryloyloxyethoxy) phenyl] fluorene (free radically polymerizable monomer), 0.4g of cationically polymerizable fluorene monomer, 0.6g of neopentyl glycol diglycidyl ether, 0.2g of the cation-reactive plasticizer, 0.05g of butyltriphenyl naphthylcarbamoyl borate (borate, N3B), 0.02g photosensitizing dye (E2), 3- ethyl-2-[3-(3-ethyl-1,3-benzothiazol -2 (3H) - ylidene) prop-1-en .sup.5-1-yl] -1,3-benzothiazole-1-ium 9 (table 1, page 16) [0066]. This composition is coated and dried to forma holographic recording film. A holograms was recorded using two beam exposure and a UV post cure was performed [0057-0064]. The radical initiator as (E1), for example, carbonyl compounds benzoin ethyl ether, benzophenone and diethoxy acetophenone, etc.;Acyl phosphine oxide compound 2,4,6-trimethyl benzoyl diphenyl phosphine oxide, bis (2,4,6-trimethyl benzoyl) phenyl phosphine oxide and the like;Organotin compounds tributylbenzyl tin and the like;Alkyl aryl borate tetrabutylammonium butyltriphenylborate, tetrabutylammonium Buchirutorisu (tert- butyl phenyl) borate, tetrabutylammonium butyltriphenyl naphthyl borate and the like; Diaryliodonium salts diphenyl iodonium hexafluorophosphate, diphenyl iodonium tetrafluoroborate, diphenyl iodonium hexafluoroantimonate and the like; iron arene complex hexafluorophosphate (1), etc. η5- cyclopentadienyl -η6- cumenyl - - Iron (1 +); Triazine compounds tris (trichloromethyl) triazine and the like; 3,3' (tert- butylperoxy) -4,4' di (methoxycarbonyl) benzophenone, 3,3 ', 4,4-tetrakis (tert- butylperoxycarbonyl) benzophenone, di - tert--butylperoxy isophthalate, 2,5-dimethyl-2,5-bis (benzoyl peroxy) hexane, organic peroxides tert--butyl peroxy benzoate; (O- chlorophenyl) -4,4 ', bis imidazole derivatives of 5,5-tetra-phenyl-1,1' bisimidazole etc. 2,2'-bis; And the like. In addition, as commercially available can be used as (E1) the radical initiator, for example, Darocure 1173, Irgacure 184, Irgacure 907, BT-2 (Chisso Co., Ltd.) (Germany BASF Corp. both), etc. may be used [0045-0047]. Also, the components other than the above, various additives cocatalyst for promoting the cationic polymerization initiator, a surfactant, a polymerization inhibitor, a chain transfer agent, a cationic polymerization reaction and radical polymerization reaction or / and an ultraviolet absorber can be added agent [0051]
Fujii et al. JP 2013182040 does not exemplify a composition including a photosensiting dye, a borate compound and 2-hydroxy-2-methyl-1-phenylpropane-1-one (darocure 1173)
It would have been obvious to one skilled in the art to modify example 1, which has 93.5% monomer based upon the sum of the free radically polymerizable monomer and the photoinitiator content, by adding 2-hydroxy-2-methyl-1-phenylpropane-1-one (darocure 1173) based upon the disclosure at [0047] and the direction to add additive which increase the radical polymerization reaction at [0051] and to have the dye, borate and 2-hydroxy-2-methyl-1-phenylpropane-1-one (darocure 1173) be present in an amount of 0.3 to 10 wt% based upon the disclosure at [0050].
Claims 16 and 18-28 are rejected under 35 U.S.C. 103 as being unpatentable over Jang et al. 2020025562 combined with Hara et al. WO 2020158300, Hara JP 2010174123, Sood et al. 20150285813, Takigawa et al. 20070207390 and Harai et al. JP H11344802.
Jang et al. 20200255623 in the preparation of the holographic phjotopolymer in the composition of example 1 combines a polyol, an isocyanate, 40.3 g of a monomer, 0.1 g of Safrinin O, 1.5 G of Ebecryl p-115, 0.26 g of borate V, 0.1 g of irgacure 250 (lodonium (4-methylphenyl)[4-(2-methylpropyl)phenyl] hexafluorophosphate) , a plasticizer, a fluorinated compound, and solvent. The refractive index modulation was 0.026 (see table 1 on page 8). Useful dyes include various commonly known compounds can be used. Specific examples of the photosensitizing dye include sulfonium derivative of ceramidonines, new methylene blue, thioerythrosine triethylammonium, 6-acetylamino-2-methylceramidonine, Eosin, Erythrosine, Rose bengal, thionine, Basic Yellow, Pinacyanol chloride, Rhodamine 6G, Gallocyanine, Ethyl Violet, Victoria Blue R, Celestine Blue, Quinaldine Red, Crystal Violet, Brilliant Green, Astrazon Orange G, Darrow Red, Pyronin Y, Basic Red 29, Pyrylium iodide, Safranin O, Cyanine, Methylene blue, Azure A, and combinations of two or more thereof, These may be used in amounts of 0.01% to 30% by weight, or 0.05% to 20% by weight [0105-0106]. Useful photoinitiators include imidazole derivatives, bisimidazole derivatives, N-aryl glycine derivatives, organic azide compounds, titanocene, aluminate complexes, organic peroxide, N-alkoxyl pyridinium salt, thioxanthone derivatives, and the like. More specific examples of the photo-radical polymerization initiator include 1,3-di(t-butyldioxycarbonyl)benzophenone, 3,3′,4,4′-tetrakis(t-butyldioxycarbonyl)benzophenone, 3-phenyl-5-isoxazolone, 2-mercaptobenzimidazole, bis(2,4,5-triphenyl)imidazole, 2,2-dimethoxy-1,2-diphenylethane-1-on (trade name: Irgacure 651, manufactured by BASF), 1-hydroxy-cyclohexyl-phenyl-ketone (trade name: Irgacure 184, manufactured by BASF), 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butane-1-one (trade name: Irgacure 369, manufactured by BASF), and bis(η5-2,4-cyclopentadien-1-yl)-bis (2,6-difluoro-3-(1H-pyrrole-1-yl)-phenyl)titanium (trade name: Irgacure 784, manufactured by BASF) or the like [0098] In addition, the photopolymerizable composition of the embodiment may include monomolecular (type I) and bimolecular (type II) initiators. (Type I) systems for free radical photopolymerization are, for example, aromatic ketone compounds, e.g. benzophenones, in combination with tertiary amines, alkylbenzophenones, 4,4′-bis(dimethylamino)benzophenone (Michler's ketone), anthrone, and halogenated benzophenones or mixtures of said types. (Type II) initiators may be benzoin and its derivatives, benzyl ketals, acylphosphine oxides, e.g. 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bisacylophosphine oxide, phenylglyoxylic esters, camphorquinone, alpha-aminoalkylphenone, alpha,alpha-dialkoxyacetophenone, 1-[4-(phenylthio)phenyl]octane-1,2-dione 2-(O-benzoyloxime), alpha-hydroxyalkylphenone, and the like [0100]. Photoinitiators can be used in amounts of 0.1% to about 10% by weight and 30-70 wt% of the photoreactive monomer [0101]. Specific examples of the optical element include optical lenses, mirrors, deflecting mirrors, filters, diffusing screens, diffraction elements, light guides, waveguides, holographic optical elements having projection screen and/or mask functions, mediums of optical memory systems and light diffusion plates, optical wavelength multiplexers, reflection and transmission types of color filters, and the like [0125].
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(borate V)
Hara et al. WO 2020158300 (machine translation attached) describes a holograms with a chromic (colored) dye having an amine structure using a decolorization agent to provide a holograms with transparency and improved diffraction characteristics (abstract). Dyes which can be discolored include By using a chromic dye that is decolorized by pH and/or redox, the sensitizing property at the time of hologram recording and the decolorizing property after exposure are easily aligned, so that the effect of the present technology is further exerted. Further, the chromic dye of the present embodiment is preferably one or more selected from thiazine compounds, azine compounds, acridine compounds, oxazine compounds and cyanine compounds. By using the chromic dye having these skeletons, the sensitizing property at the time of hologram recording and the decolorizing property after exposure are easily aligned, so that the effect of the present technology is further exerted. Specific examples of the chromic dye of the present embodiment include methylene blue, safranine o, astrazone orange G, acridine orange, acridine yellow, thionine, toluidine blue o, and neutral red, but are not limited thereto. It is not something that will be done [0024-0028]. When an onium salt-based initiator and an aryl borate salt-based initiator are used in combination, the polymerization initiation effect during hologram recording and the effect of improving the decoloring property of the chromic dye after exposure can be further improved. It is possible, and the effect of the present technology is further exerted [0033]. When the hologram recording medium is exposed and light is incident on the photosensitive layer, part of the methylene blue excited by the light is reduced by the triarylborate salt and the color is erased. Since the decolorized substance of methylene blue has a secondary amino group, a part of the decolorized substance of methylene blue reacts with an epoxy monomer, and the structure of the decolorized substance is fixed (irreversible). On the other hand, the onium salt causes a concerted reaction in which a part of the decolorized substance of methylene blue is reoxidized (recolored), and radicals and acids are generated [0059-0060].
Hara JP 2010174123 (machine translation attached) teaches that to provide a resin composition for an optical element, which does not have the discoloration caused by photopolymerization and is excellent in characteristics, and to provide a hybrid optical element. <P>SOLUTION: The resin composition for the optical element is provided by containing at least one photo-polymerizable substance having an aromatic ring in its chemical structure and having ≥0.10 and ≤4.00 mass ratio of the blending amount A of an initiating agent for generating benzoyl radicals to the blending amount B of a hindered phenol-based antioxidant (A/B), wherein the hybrid optical element is obtained by curing the resin composition layer formed on an optical member to make the layer as one unit with the optical member (abstract). Photoinitiators for generating benzoyl radicals used in the present invention include 4-dimethylaminobenzoic acid, 4-dimethylaminobenzoic acid ester, alkoxyacetophenone, benzyldimethyl ketal, benzophenone and benzophenone derivatives, alkyl benzoylbenzoate, bis (4-dialkylaminophenyl) ketone, benzyl and benzyl derivatives, benzoin and benzoin derivatives, benzoin alkyl ether, 2-hydroxy-2-methylpropiophenone, 1-hydroxycyclohexyl phenyl ketone, thioxanthone and thioxanthone derivatives, 2, 4, Examples include 6-trimethylbenzoyldiphenylphosphine oxide. These photoinitiators can be used alone or in combination of two or more [0015].
Takigawa et al. 20070207390 establishes that it is known to use dye discoloration to generate holographic images [0038,0049]. Further, a hologram recording method for forming interference fringes via refractive index modulation is preferable, which uses a discoloring agent precursor different from a discolorable dye and a sensitizing dye, the hologram recording method comprising generating an excited state of the sensitizing dye or the discolorable dye via hologram exposure, generating a discoloring agent from the discoloring agent precursor via energy transfer or electron transfer to the discoloring agent precursor, and allowing the discoloring agent to discolor the discolorable dye. Then, the discoloring agent is preferably any of radicals, acids, bases, nucleophilic agents, electrophilic agents, and singlet oxygen. Hence, the discoloring agent precursor is preferably any of radical generators, acid generators, base generators, nucleophilic agent-generating agents, electrophilic agent-generating agents, and triplet oxygen. The discoloring agent precursor is preferably any of radical generators, acid generators, and base generators, more preferably acid generators [0277]. the discolorable dye preferably includes for example cyanine dye, squalirium cyanine dye, styryl dye, pyrilium dye, merocyanine dye, benzylidene dye, oxonol dye, coumarin dye, pyran dye, xanthene dye, thioxanthene dye, phenothiazine dye, phenoxazine dye, phenazine dye, phthalocyanine dye, azaporphylline dye, porphylline dye, condensed-ring aromatic dyes, perylene dye, azomethine dye, azo dye, anthraquinone dye, and metal complex dyes, and is more preferably any of cyanine dye, styryl dye, merocyanine dye, benzylidene dye, oxonol dye, coumarin dye, xanthene dye, azomethine dye, azo dyes, and metal complex dyes. [0282].
Sood et al. 20150285813 describes the use of radical photoinitiators to bleach dyes. In some embodiments, the irradiation of the sample in step (d) initiates a chemical reaction that substantially inactivates the signal generator by radicals produced through light excitation of the photoinitiator. In certain embodiments, the radicals produced by light excitation of the photoinitiator comprise alkyl, aryl, or halogen radicals [0034,0043]. “fluorophore” or “fluorescent signal generator” refers to a chemical compound, which when excited by exposure to a particular wavelength of light, emits light at a different wavelength. Fluorophores may be described in terms of their emission profile, or “color.” Green fluorophores (for example Cy3, FITC, and Oregon Green) may be characterized by their emission at wavelengths generally in the range of 515-540 nanometers. Red fluorophores (for example Texas Red, Cy5, and tetramethylrhodamine) may be characterized by their emission at wavelengths generally in the range of 590-690 nanometers. Examples of fluorophores include, but are not limited to, 4-acetamido-4′-isothiocyanatostilbene-2,2′disulfonic acid, acridine, derivatives of acridine and acridine isothiocyanate, 5-(2′-aminoethyl)aminonaphthalene-1-sulfonic acid (EDANS), 4-amino-N-[3-vinylsulfonyl)phenyl]naphthalimide-3,5 disulfonate (Lucifer Yellow VS), N-(4-anilino-1-naphthyl)maleimide, anthranilamide, Brilliant Yellow, coumarin, coumarin derivatives, 7-amino-4-methylcoumarin (AMC, Coumarin 120), 7-amino-trifluoromethylcouluarin (Coumaran 151), cyanosine; 4′,6-diaminidino-2-phenylindole (DAPI), 5′,5″-dibromopyrogallol-sulfonephthalein (Bromopyrogallol Red), 7-diethylamino-3-(4′-isothiocyanatophenyl)-4-methylcoumarin, -, 4,4′-diisothiocyanatodihydro-stilbene-2,2′-disulfonic acid, 4,4′-diisothiocyanatostilbene-2,2′-disulfonic acid, 5-[dimethylamino]naphthalene-1-sulfonyl chloride (DNS, dansyl chloride), fluorescein and derivatives such as 5-carboxyfluorescein (FAM), 5-(4,6-dichlorotriazin-2-yl)aminofluorescein (DTAF), 2′7′-dimethoxy-4′5′-dichloro-6-carboxyfluorescein (JOE), fluorescein, fluorescein isothiocyanate (FITC), QFITC (XRITC); fluorescamine derivative (fluorescent upon reaction with amines); IR144; IR1446; Malachite Green isothiocyanate; 4-methylumbelliferone; ortho cresolphthalein; nitrotyrosine; pararosaniline; Phenol Red, B-phycoerythrin; o-phthaldialdehyde derivative (fluorescent upon reaction with amines); pyrene and derivatives such as pyrene, pyrene butyrate and succinimidyl 1-pyrene butyrate; Reactive Red 4 (Cibacron® Brilliant Red 3B-A), rhodamine and derivatives such as 6-carboxy-X-rhodamine (ROX), 6-carboxyrhodamine (R6G), lissamine rhodamine B sulfonyl chloride, rhodamine (Rhod), rhodamine B, rhodamine 123, rhodamine X isothiocyanate, sulforhodamine B, sulforhodamine 101 and sulfonyl chloride derivative of sulforhodamine 101 (Texas Red); N,N,N′,N′-tetramethyl-6-carboxyrhodamine (TAMRA); tetramethyl Rhodamine, tetramethyl rhodamine isothiocyanate (TRITC); riboflavin; rosolic acid and lathanide chelate derivatives, cyanines, pyrelium dyes, squaraines, 1,3-dichloro-7-hydroxy-9,9-dimethyl-2(9H)-Acridinone (DDAO), and dimethylacridinone (DAO). In some embodiments, the fluorophore can be cyanine, rhodamine, BODIPY or 1,3-dichloro-7-hydroxy-9,9-dimethyl-2(9H)-Acridinone (DDAO) dyes. In a preferred embodiment, the fluorophore is a cyanine dye. In a further embodiment, the cyanine dye is Cy3 or Cy5 [0089]. A signal generator may essentially include a fluorophore. In some embodiments, a signal generator may essentially include a fluorophore attached to an antibody, for example, in an immunohistochemistry analysis. Suitable fluorophores that may be conjugated to a primary antibody include, but are not limited to, Fluorescein, Rhodamine, Texas Red, VECTOR Red, ELF (Enzyme-Labeled Fluorescence), Cy2, Cy3, Cy3.5, Cy5, Cy7, Fluor X, Calcein, Calcein-AM, CRYPTOFLUOR, Orange (42 kDa), Tangerine (35 kDa), Gold (31 kDa), Red (42 kDa), Crimson (40 kDa), BHMP, BHDMAP, Br-Oregon, Lucifer Yellow, Alexa dye family, N-[6-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino]caproyl] (NBD), BODIPY, boron dipyrromethene difluoride, 1,3-dichloro-7-hydroxy-9,9-dimethyl-2(9H)-Acridinone (DDAO), dimethylacridinone (DAO), Oregon Green, MITOTRACKER Red, Phycoerythrin, Phycobiliproteins BPE (240 kDa) RPE (240 kDa) CPC (264 kDa) APC (104 kDa), Spectrum Blue, Spectrum Aqua, Spectrum Green, Spectrum Gold, Spectrum Orange, Spectrum Red, Infra-Red (IR) Dyes, Cyclic GDP-Ribose (cGDPR), Calcofluor White, Lissamine, Umbelliferone, Tyrosine or Tryptophan. In some embodiments, the fluorophore can be cyanine, rhodamine, coumarins or pyrelium dyes. In some embodiments, a signal generator may essentially include a cyanine dye. In further embodiments, a signal generator may essentially include one or more of a Cy2 dye, a Cy3 dye, a Cy5 dye, or a Cy7 dye. In alternative embodiments, the signal generator may be BODIPY, rhodamine, 1,3-dichloro-7-hydroxy-9,9-dimethyl-2(9H)-Acridinone (DDAO) or 7-hydroxy-9,9-dimethyl-2(9H)-Acridinone (DAO) [0165]. “photoinitiator” or “radical photoinitiator” refers to a compound especially added to a formulation to convert absorbed light energy, UV or visible light, into chemical energy in the form of initiating species, e.g., free radicals Based on the mechanism by which radicals are formed, photoinitiators are generally divided into two classes. Type I photoinitiators undergo a unimolecular bond cleavage upon irradiation to yield free radicals. Type II photoinitiators undergo a bimolecular reaction where the excited state of the photoinitiator interacts with a second molecule (a coinitiator) to generate free radicals. UV photoinitiators of both Type I and Type II are available. However, visible light photoinitiators belong almost exclusively to the Type II class of photoinitiators. An exemplary list of photoinitiators is provided below, as well as in Table 1. For photoinitiation to proceed efficiently, the absorption bands of the photoinitiator must overlap with the emission spectrum of the source [0098]. A photoinitiator (or a radical photoinitiator) is a compound which may convert absorbed light energy, UV or visible light, into chemical energy in the form of initiating species, e.g., free radicals. When a UV or visible light source (250-700 nm wavelength) is shone onto a transparent container that includes the photoinitiator and the dye stained biological sample (e.g., tissue sample on a glass slide), the photons of light directly excite the photoinitiator molecule and generate initiating species, e.g., free radicals. The radicals attack the dye molecule and chemically modify the dye structure and alter its optical properties. The alkyl, aryl or halogen radical formed as a result of excitation of photoinitiators, is added to the carbon-carbon double bond of the dye and thus inactivates the dye. In other embodiments, the photoinitiators also comprise benzoin ethers, camphorquinone, anthraquinone, benzil, aminoalkylphenones, thioxanthone, Acylphosphine oxides, polysilanes, alpha-dialkyloxy acetophenones, a-hydroxyalkylphenones or Titanocenes [0177,0185]. Commonly Used Photoinitiators (The Sigma Aldrich product number coded is followed by the Photoinitiator name) A1,070-1 Acetophenone, 99% A8,840-9 Anisoin, 95% A9,000-4 Anthraquinone, 97% 12,324-2 Anthraquinone-2-sulfonic acid, sodium salt monohydrate, 97% 11,931-8 (Benzene) tricarbonylchromium, 98% B515-1 Benzil, 98% 39,939-6 Benzoin, sublimed, 99.5+% 17,200-6 Benzoin ethyl ether, 99% 19,578-2 Benzoin isobutyl ether, tech., 90% B870-3 Benzoin methyl ether, 96% B930-0 Benzophenone, 99% 40,562-0 Benzophenone/1-Hydroxycyclohexyl phenyl ketone, 50/50 blend 26,246-3 3,3′,4,4′-Benzophenonetetracarboxylic dianhydride, sublimed, 98% B1,260-1 4-Benzoylbiphenyl, 99% 40,564-7 2-Benzyl-2-(dimethylamino)-4′-morpholinobutyrophenone, 97% 16,032-6 4,4′-Bis(diethylamino)benzophenone, 99+% 14,783-4 4,4′-Bis(dimethylamino)benzophenone, 98% 12,489-3 Camphorquinone, 98% C7,240-4 2-Chlorothioxanthen-9-one, 98% 40,807-7 (Cumene)cyclopentadienyliron(II) hexafluorophosphate, 98% D3,173-7 Dibenzosuberenone, 97% 22,710-2 2,2-Diethoxyacetophenone, 95% D11,050-7 4,4′-Dihydroxybenzophenone, 99% 19,611-8 2,2-Dimethoxy-2-phenylacetophenone, 99% 14,934-9 4-(Dimethylamino)benzophenone, 98% 14,670-6 4,4′-Dimethylbenzil, 97% D14,966-7 2,5-Dimethylbenzophenone, tech., 95% D14,967-5 3,4-Dimethylbenzophenone, 99% 40,566-3 Diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide/2- Hydroxy-2-methylpropiophenone, 50/50 blend 27,571-9 4′-Ethoxyacetophenone, 98% E1,220-6 2-Ethylanthraquinone, 97+% F40-8 Ferrocene, 98% 32,810-3 3′-Hydroxyacetophenone, 99+% 27,856-4 4′-Hydroxyacetophenone, 99% 22,043-4 3-Hydroxybenzophenone, 99% H2,020-2 4-Hydroxybenzophenone, 98% 40,561-2 1-Hydroxycyclohexyl phenyl ketone, 99% 40,565-5 2-Hydroxy-2-methylpropiophenone, 97% 15,753-8 2-Methylbenzophenone, 98% 19,805-6 3-Methylbenzophenone, 99% M3,050-7 Methybenzoylformate, 98% 40563-9 2-Methyl-4′-(methylthio)-2-morpholinopropiophenone, 98% 15,650-7 Phenanthrenequinone, 99+% 29,074-2 4′-Phenoxyacetophenone, 98% T3,400-2 Thioxanthen-9-one, 98% (table 1)
Harai et al. JP H11344802 (machine translation attached) eximplifies a photosensitive printing plate including a binder, an infrared absorbing dye, tetrabutylamminium n-butyltriphenyl boron and crystal violet (colorant) (example 1). The boron/borate salt (of formulae 1 and 2) includes tetraalkyl ammonium borate salts which acts as a decolorizing agent (abstract).The infrared absorbing dye used in the present invention, cyanine, triarylmethane, aminium, diimmonium, thiazine, xanthene, oxazine, styryl, pyrylium, thiopyrylium, squalilium, croconium, azulhenium, etc. having an absorption in the near infrared region [0011]
Jang et al. 20200255623 does not exemplify a photopolymer composition including a photoinitiator which generates both a benzoyl and alcohol radical upon exposure or establish that the borate and benzoyl and alcohol radical generating photoinitiator inherently bleach the sensitizing dyes.
With respect to claims 16 and 18-28, it would have been obvious to one skilled in the art to modify the identified/cited compositions of the examples by replacing the irgacure 250 with 2-hydroxy-2-methylpropiophenone taught in Hara JP 2010174123 as useful in initiating photopolymerization with a reasonable expectation of forming a useful holographic composition based upon their disclosed equivalent function. The examiner cites Hara et al. WO 2020158300 to establish that the borate anions as known in the holographic art to bleach sensitizing dyes, which makes the holograms transparent and have higher refractive index modulation and Harai et al. JP H11344802. To establish that the use of ammonium salts to bleach dyes in photosensitive composition is old and well known. The examiner cites Takigawa et al. 20070207390 to establish that the use of radical generating photoinitiators to bleach dyes is known in the holographic arts, Sood et al. 20150285813 which establishes that free radical photoinitiators are inherently able to bleach dyes and Hara JP 2010174123 who establishes that benzoyl radical generating photoinitiators in particular are known bleaching agents which remove/reduce discoloration in optical elements.
With respect to claims 16 and 18-28, it would have been obvious to one skilled in the art to modify the identified/cited compositions of the examples by replacing by replacing the irgacure 250 with 2-hydroxy-2-methylpropiophenone taught in Hara JP 2010174123 as useful in initiating photopolymerization and replacing the safrin -O with methylene blue with a reasonable expectation of forming s useful holographic composition based upon their disclosed equivalent function. The examiner cites Hara et al. WO 2020158300 to establish that the borate anions as known in the holographic art to bleach sensitizing dyes, which makes the holograms transparent and have higher refractive index modulation and Harai et al. JP H11344802. To establish that the use of ammonium salts to bleach dyes in photosensitive composition is old and well known. The examiner cites Takigawa et al. 20070207390 to establish that the use of radical generating photoinitiators to bleach dyes is known in the holographic arts, Sood et al. 20150285813 which establishes that free radical photoinitiators are inherently able to bleach dyes and Hara JP 2010174123 who establishes that benzoyl radical generating photoinitiators in particular are known bleaching agents which remove/reduce discoloration in optical elements.
In the response of 6/25/2026, the applicant argues that there is improved bleaching in the example when Irgacure 1173 is used, rather than Irgacure 184. The examiner points out that the example of Jang et al. 20200255623 uses irgacure 250, not irgacure 184 and it is not clear why the cited example is equal or preferable to a direct comparison with the prior art. Additionally, the scope of the showing appears to be limited to specific dyes and ammonium borates. The showing is not commensurate in scope with the coverage sought.
Claims 16 and 18-28 are rejected under 35 U.S.C. 103 as being unpatentable over Jang et al. 20200255623 combined with Hara et al. WO 2020158300, Hara JP 2010174123, Sood et al. 20150285813, Takigawa et al. 20070207390 and Harai et al. JP H11344802, in view of Smothers et al. 5147758.
Smothers et al. 5147758 teaches borates including (2-Hydroxyethyl)trimethylammonium triphenylbutyl borate, choline triphenylbutylborate, Tetramethylammonium triphenylbutyl borate and Tetrabutylammonium tetraphenylborate (17/35-36,18/41-44). The addition of borate salts are evidenced in table 7 to increase sensitivity (col 31) and borate co-initiators are known in the art (col 1/line 57-col 2/line 9). The recording of holograms is disclosed (col 3/lines 16+). They can also be used as holographic notch filters when it is desired to protect against more than one wavelength of radiation (17/1-19)
Jang et al. 20200255623 does not disclosed the tetrabutyl ammonium borates of claim 17.
In addition to the basis above, the examiner holds that it would have been obvious to one skilled in the art to modify the compositions and processes using them rendered obvious by Jang et al. 20200255623 combined with Hara et al. WO 2020158300, Hara JP 2010174123, Sood et al. 20150285813, Takigawa et al. 20070207390 and Harai et al. JP H11344802 by replacing the borate V co-initiator with other borate co-initiators known to be useful in the holograsphic photopolymer art such as the tetrabutylammonium borates taught by Smothers et al. 5147758 with a reasonable expectation of forming a useful holographic recording medium
Claims 16 and 18-28 are rejected under 35 U.S.C. 103 as being unpatentable over Jang et al. 20200255623 combined with Hara et al. WO 2020158300, Hara JP 2010174123, Sood et al. 20150285813, Takigawa et al. 20070207390 and Harai et al. JP H11344802, in view of Smothers et al. 5147758, further in view of Sato et al. EP 1970761.
Sato et al. EP 1970761 teaches sensitizers include compounds belonging to the kinds recited below, and that having absorption wavelengths in a range of 350 nm to 450 nm and include polynuclear aromatic hydrocarbons (e.g., pyrene, perylene, triphenylene, anthracene), xanthenes (e.g., fluorescein, Eosine, Erythrocin, Rhodamine B, Rose Bengale), cyanines (e.g., thiacarbocyanine, oxacarbocyanine), mercoeyanines (e.g., merocyanine, carbomerocyanine), thiazines (e.g., Thionine, Methylene Blue, Toluidine Blue), acridines (e.g., Acridine Orange, chloroflavin, acriflavine), anthraquinones (e.g., anthraquinone), squaryliums (e.g., squarylium), and coumarins (e.g., 7-diethylamino-4-methylcoumarin) [0126-0127].
In addition to the basis above, the examiner holds that it would have been obvious to modify the compositions and holographic devices rendered obvious by the combination of Jang et al. 20200255623, Hara et al. WO 2020158300, Hara JP 2010174123, Sood et al. 20150285813, Takigawa et al. 20070207390, Harai et al. JP H11344802 and Smothers et al. 5147758, by using replacing the safranin O or methylene blue with other heterocyclic photosensitizers such as Rhodamine B, acridine, acriflavine known in the art based upon their equivalence established in Sato et al. EP 1970761, noting that these are established as bleachable in at least one of Hara et al. WO 2020158300, Hara JP 2010174123, Sood et al. 20150285813, Takigawa et al. 20070207390 and Harai et al. JP H11344802 with a reasonable expectation of forming a useful holographic recording material and holographic articles formed from those compositions.
Claims 16-28 are rejected under 35 U.S.C. 103 as being unpatentable over Jang et al. 20200255623 combined with Hara et al. WO 2020158300, Hara JP 2010174123, Sood et al. 20150285813, Takigawa et al. 20070207390, Harai et al. JP H11344802 and Sato et al. EP 1970761, further in view of Kondo et al. JP-H09109352
In addition to the basis above, it would have been obvious to one skilled in the art to modify the composition and processes of using them rendered obvious by the combination of Jang et al. 20200255623 combined with Hara et al. WO 2020158300, Hara JP 2010174123, Sood et al. 20150285813, Takigawa et al. 20070207390, Harai et al. JP H11344802 and Sato et al. EP 1970761 by replacing the quaternary ammonium borate salt with others bounded by the teachings including those with tetramethylammonium or tetrabutylammonium cations and tetrahexylboron or hexyltriphenylboron anions based upon the teachings at [0022-0029] of
Kondo et al. JP-H09109352 with a reasonable expectation of forming a useful photosensitive composition. Additionally, Kondo et al. JP-H09109352 supports the equivalence of onium photoinitiators and 2-hydroxy-2-methylpropiophenone at
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claims 16-28 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claim of copending Application No. 18276755 (20240150569). Although the claims at issue are not identical, they are not patentably distinct from each other because claim 16 recites
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Claim 18 recites
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Claims 20 and 21 recite:
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Claims 26-27 recite
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This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
It would have been obvious to one skilled in the art to mix the dye concentrate and monomer mixture using the benzoyl and alcohol generating photoinitiator2-hydroxy-2-methylpropiophenoneof claim 18, the dyes of claim 20 and the co-initiator of claim 21 to forma composition which embraces claims 16-28 of the instant application. The examiner notes the utility recited in claims 26-28 of the copending application.
The applicant states that a terminal disclaimer was filed with the amendment. This is not the case, therefore the rejection stands. (although it appears that the fee may have been paid)
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
Ezaki et al. JP H09118706 exemplifies a composition including as an initiator the combination of (0.02 parts 3,3'-diethyl-2,2'-thiatricarbocyanine iodide (cyanine dye), 1.4 parts 2,4,6-Tris (trichloromethyl) -1,3,5-triazine and 1.4 parts tetramethylammonium n-butyltriphenylborate or the combination of 0.32 parts dye NK-3965 (organic boron compound), 2 parts of Darocure 117 (2-hydroxy-2-methylpropiophenone)) with the polymerizable composition 40 parts urethane acrylate (UVR 2003), 40 parts monomer NK ester ADP-6, 20 parts RNK 0248 and 0.3 parts megafac F177 (surfactant). This composition was exposed using RuI/KI filtered Hg lamp [0032-0035]. The organic boron salt that can be used in the present invention is represented by the formula
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Wherein R10,R11,R12 and R13 are independently hydrogen, C1-C10, preferably C1-C4 alkyl, C6-C15, preferably C6-C10 aryl, C2-C10, preferably C2-C5 alkaryl, allyl, C1-C10, preferably C1-C4 aralkyl, C1-C10, preferably C1-C4 alkenyl, C1-C10, preferably C1-C4 alkynyl or silyl, and R14,R15,R16 and R17 are independently C1-C10, preferably C1-C4 alkyl, C6-C15, preferably C6-C10 aryl, C2-C10, preferably C2-C5 alkaryl, allyl, C1-C10, preferably C1-C4 aralkyl, C1-C10, preferably C1-C4 alkenyl or C1-C10, preferably C1-C4 alkynyl, provided that at least one of them is alkyl. The quaternary ammonium salt of organic boron is represented by formula (1). Specific examples of the organic boron salt which can be particularly preferably used in the present invention include tetramethylammonium triphenyl n-butylborate, tetramethylammonium triphenyl n-octylborate, tetraethylammonium triphenyl n-butylborate, ammonium triphenyl n-butylborate, tetramethylammonium trinisyl n-butylborate, tetramethylammonium tetraphenylborate, and tetraethylammonium diphenyldi-n-butylborate. The organic boron salt is contained in the near-infrared polymerizable composition of the present invention in an amount of 0.1 to 20 parts by weight, preferably 1 to 10 parts by weight, based on 100 parts by weight of the ethylenically unsaturated compound. When the amount of the organic boron salt is less than 0.1 part by weight, the curing becomes insufficient, and when it exceeds 20 parts by weight, the solvent resistance and the like of the cured product are lowered [0024-0027]. A photopolymerizable composition having sensitivity to both the near-infrared light and the ultraviolet light or both the near-infrared light and the visible light is used. Such photopolymerizable compositions are already known (for example, Japanese Patent Application Laid-Open No. 64 (1989) - 72150). More specifically, the composition contains an initiator which is sensitive to light in the near-infrared region and the ultraviolet region or visible light, a monomer which causes addition polymerization by the action of the initiator, and, if necessary, other additives or resins. Examples of the initiator having sensitivity to near-infrared light include a salt of a near-infrared absorbing cationic dye, a combination of a near-infrared absorbing cationic dye and an ammonium salt, and a combination of a near-infrared absorbing cationic dye, a triazine compound, and an ammonium salt. Examples of initiators sensitive to the ultraviolet region include acetophenone initiators, benzoin initiators, benzophenone initiators, and thioxanthone initiators. Further comprising: Examples of the initiator sensitive to the visible region include a combination of an organic peroxide and chlorophyll, a combination of an organic peroxide and eosin G, a combination of an organic peroxide and riboflavin, a combination of an organic peroxide and methylene blue, a combination of an organic peroxide and (thio) pyrylium salts, a combination of an organic peroxide and merocyanine, a combination of an organic peroxide and quinoline, a combination of an organic peroxide and styrylquinone, a combination of an organic peroxide and (thio) xanthene dyes, a combination of an organic peroxide and riboflavin tetrabutylate, a combination of an organic peroxide and (keto) coumarin dyes, a combination of an organic peroxide, N-phenylglycine , and a rhodanine derivative polymer, a combination of diphenyliodonium salts and merocyanine dyes, a combination of diphenyliodonium salts and ketocoumarin dyes, a combination of diphenyliodonium salts and tetraphenylporphyrin dyes, a combination of diphenyliodonium salts and tetrabenzoporphyrin, a combination of diphenyliodonium salts and spiropyran, a combination of diphenyliodonium salts, N-phenylglycine , and thioxanthene dyes, a combination of diphenyliodonium salts, N-phenylglycine , and melone A cyanine-based dye, an alkylborate of a cyanine-based dye, an alkylborate of a rhodamine-based dye, an alkylborate of a methylene blue-based dye, an iron-arene complex, a combination of an iron-arene complex and a ketocoumarin-based dye, a combination of an iron-arene complex and a thioxanthene-based dye, a fluorine-substituted titanocene, a combination of a bisimidazole and an arylylidene aryl ketone, a combination of a bisimidazole and a ketocoumarin-based dye, a combination of a N-phenylglycine and a ketocoumarin-based. Examples thereof include a combination with a cyanine dye; a combination with N-phenylglycine and a (thio) xanthene dye; a combination with a tris(trichloromethyl)-s-triazine derivative or a tris(trichloromethyl)-s-triazine derivative and a merocyanine dye; a combination with a tris(trichloromethyl)-s-triazine derivative and a ketocoumarin dye; a combination with a tris(trichloromethyl)-s-triazine derivative and a thiopyrylium salt; a combination with a tris(trichloromethyl)-s-triazine derivative and a thioxanthene dye; a combination with an aminobenzoate and riboflavin tetrabutyrate; and a combination with a and a thiopyrylium salt. 2-mercaptobenzimidazole Examples of monomers which are polymerized by the action of a photopolymerization initiator include compounds having an ethylenically unsaturated double bond which are generally used in such a photocurable composition [0008]
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Sugita et al. JP H10316728 (machine translation attached) teaches 50 parts of the polymerizable compound.
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, 0.1 parts of tetra-n-butylammonium triphenyl-n-butyl borate, 1.0 part of 2-hydroxy-2- methylpropiophenone (Darocur 1173) and 50 parts talc, which was cured using a halide lamp [0054] Example 3 A curable composition was prepared in the same manner as in Example 2 except that the organoboron compound was changed to tetra-n-butylammonium tri (pt-butylphenyl) -n-butylborate. Produced. A light curing test was performed in the same manner as in Example 1. As a result, the surface hardness was 73 and the back surface hardness was 72 in 30 minutes of the irradiation time. There was no surface tack [0056]. curable unsaturated compound was converted to 25 parts of a vinyl ester (trade name: Evecryl 3702, manufactured by Daicel UCB) and 25 parts, phenoxyethyl acrylate 25. The curable composition was prepared in exactly the same manner as in Example 2 except that the mixture was changed to a mixture of parts. When a light curing test was performed in the same manner as in Example 1, the surface hardness was 67 and the back surface hardness was 66 at an irradiation time of 30 minutes, and it was sufficiently cured [0062]. As described above, a polymerization initiator system combining an organic boron compound and a dye or an organic boron compound and an acidic compound is known, but a combination of an organic boron compound and an ultraviolet light polymerization initiator is known. No initiator system synergistically exhibiting good polymerization initiation ability has been known [0016]. A visible light polymerization initiator having photosensitivity in the visible light region can be contained [0028]
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). 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.
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MARTIN J. ANGEBRANNDT
Primary Examiner
Art Unit 1737
/MARTIN J ANGEBRANNDT/Primary Examiner, Art Unit 1737 August 5, 2026
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