Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Compositions to be polymerized by wave energy wherein said...
Reexamination Certificate
2001-04-17
2003-03-11
Seidleck, James J. (Department: 1711)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Compositions to be polymerized by wave energy wherein said...
C522S001000, C522S090000, C522S096000, C522S100000, C522S101000, C522S103000, C522S104000, C522S149000, C522S150000, C522S151000, C522S152000, C522S153000, C522S154000, C522S182000, C528S50200C, C528S50200C, C053S428000
Reexamination Certificate
active
06531521
ABSTRACT:
BACKGROUND OF THE INVENTION
The present invention relates to a method of preserving a photosensitive composition, such as a photosensitive resin composition suitable for a resist and the like used for producing a color filter used in a color liquid crystal display apparatus, image element and the like,
Conventionally, a photosensitive composition is placed and preserved in a light shielding vessel such as a brown glass bottle and the like. However, change of the viscosity by time of the photosensitive composition, generation of aggregations and the like are sometimes caused, during the preservation thereof in a shielding vessel. Such change of the viscosity and generation of aggregations often stop the coating line of this composition.
The present inventors have intensively studied for improving preservation stability of a photosensitive composition in view of such problems. As the result, they have found that preservation stability of the photosensitive composition can be improved remarkably by controlling the void ratio and oxygen partial pressure in a vessel filled with this composition. Thus, the present invention was completed.
SUMMARY OF THE INVENTION
The present invention provides a practically excellent method for preserving a photosensitive composition containing a photopolymerization initiator and a photopolymerizable monomer and/or oligomer, which comprises placing the photosensitive composition in a vessel, wherein the product of the void ratio (%) in the vessel and the oxygen partial pressure (hpa) in the void part is 1500 (%·hPa) or more.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
The photosensitive composition of the present invention contains a photopolymerization initiator and at least one selected from photopolymerizable monomers and photopolymerizable oligomers. As the photopolymerization initiator, one which is usually used in this field may be used. Examples thereof include acetophenone-based initiators, benzoin-based initiators, benzophenone-based initiators, thioxanetone-based initiators, triazine-based initiators, and other initiators.
Specific examples of the acetophenone-based photopolymerization initiator include oligomers of diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzyldimethylketal, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propan-1-one, 1-hydroxycyclohexylphenylketone, 2-methyl-2-morpholino-1-(4-methylthiophenyl)propan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)butan -1-one or 2-hydroxy-2-methyl-1-[4-(1-methylvinyl)phenyl] propan-1-one.
Specific examples of the benzoin-based photopolymerization initiator include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, and the like.
Specific examples of the benzophenone-based photopolymerization initiator include benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4′-methyldiphenyl sulfide, 3,3′,4,4′-tetra(tert-butyl peroxycarbonyl)benzophenone, 2,4,6-trimethylbenzophenone.
Specific examples of the thioxanetone-based photopolymerization initiator include 2-isopropylthioxanetone, 4-isopropylthioxanetone, 2,4-diethylthioxanetone, 2,4-dichlorothioxanetone, 1-chloro-4-propoxythioxanetone, and the like.
Specific examples of the triazine-based photopolymerization initiator include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl) -1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl -1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, 2,4-bis(trichloromethyl) -6- [2-(5-methylfuran-2-yl)ethenyl ]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphe nyl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine, and the like.
Specific examples of the other photopolymerization initiator include 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 2,2′-bis(o-chlorophenyl)-4.4′,5,5′-tetraphenyl -1,2′-biimidazole, 10-butyl-2-chloroacridone, 2-ethylanthraquinone, benzyl, 9,10-phenanthrenequinone, camphorquinone, methyl phenylglyoxylate, titanocene compounds, and the like. These photopolymerization initiators can also be used alone or in combination of two or more.
In the present invention, a photoinitiation assistant can also be used in combination with a photopolymerization initiator. As the photoinitiation assistant, amine-based photoinitiation assistants and alkoxyanthracene-based photoinitiation assistants are exemplified.
Specific examples thereof include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethyl p-toluidine, 4,4′-bis (dimethylamino)benzophenone (common name: Michler's ketone), 4,4′-bis(diethylamino)benzophenone, 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene and the like- These photoinitiation assistants can also be used alone or in combination of two or more of them
Total amount of the photopolymerization initiators and photoinitiation assistants in the photosensitive composition of the present invention is generally from 3 to 30 parts by weight, preferably from 5 to 25 parts by weight, based on 100 parts by weight of the total solid content (excluding a solvent when used).
The photopolymerizable monomer and/or oligomer is a compound which causes polymerization by action of light and a photopolymerization initiator. In general, compounds having a polymerizable carbon-carbon unsaturated bond are examples thereof.
This photopolymerizable monomer can be selected from bi-functional monomers and other poly-functional monomers, in addition to mono-functional monomers. Specific examples of the mono-functional monomer include nonylphenylcarbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexylcarbitol acrylate, 2-hydroxyethyl acrylate, N-vinylpyrrolidone and the like. Specific examples of the bi-functional monomer include 1,6-hexanediol di(meth)acrylate, ethyleneglycol di(meth)acrylate, neopentylglycol di(meth)acrylate, triethyleneglycol di(meth)acrylate, bis(acryloyloxyethyl) ether of bisphenol A, 3-methylpentanediol di(meth)acrylate, tricyclodecanedimethanol di(meth)acrylate and the like.
Specific examples of the other poly-functional monomer include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythriol penta(meth)acrylate, dipentaerythriol hexa(meth)acrylate, tris(methacryloyloxyethyl) isocyanurate and the like. The photopolymerizable monomers can also be used alone or in combination of two or more,
The photopolymerizable oligomer can be selected from oligomers having an acryloyl group, methacryloyl group, vinyl group or the like. Specifically, urethane acrylates such as urethane acrylate and urethane methacrylate, epoxy acrylates such as epoxy acrylate and epoxy methacrylate, polyester acrylates such as polyester acrylate and polyester methacrylate, melamine acrylates such as melamine acrylate and melamine methacrylate, acrylic resin acrylates, unsaturated polyesters, polyenes and the like are exemplified
Examples of the urethane acrylates include those obtained by reacting an organic polyisocyanate, a polyol and a hydroxyacrylate-based compound, and those obtained by reacting an organic polyisocyanate and a hydroxyacrylate-based compound.
Examples of the epoxyacrylates include those obtained by reacting an acrylic acid and/or a methacrylic acid with an epoxy resin such as a bisphenol A type epoxy resin or a novolak type epoxy resin. Examples of the polyester acrylates include those obtained by reacting an acrylic acid and/or a methacrylic acid with a polyester polyol synthesized from a poly-hydric alcohol and a poly-valent carboxylic a
Baba Koji
Hozumi Shigeo
Inoue Toshiya
McClendon Sanza L.
Seidleck James J.
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