Classifications

• • G—PHYSICS
  • G02—OPTICS
  • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
  • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
  • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/04—Oxygen-containing compounds
  • C08K5/05—Alcohols; Metal alcoholates
  • C08K5/057—Metal alcoholates

Definitions

• the present invention relates to a plastic lens, a prism, an optical fiber, an information recording substrate, and a filter.
• Liquid crystal display members plasma display members, prism sheets, diffusers, light scattering films, viewing angle enhancement films, brightness enhancement films, polarizers, film-like optical members typified by solar cells
• the present invention relates to a thin-film optical member having a high refractive index and a resin material thereof.
• the high refractive index resin material in the prior art is a thiourethane obtained from a polythiol compound and a polyisocyanate compound (Japanese Patent Publication No. 4-58489), a polymer obtained from an epoxy resin or an episulfide resin ( (Japanese Unexamined Patent Publication No. 3-81320)), but these high-refractive resins have a refractive index limit of about 1.72, and in addition to the process of intense odor before curing. Subject to restrictions. A polymer in which bromine is introduced into the benzene ring has already been commercialized, but its refractive index is about 1.6.
• the Japanese Patent Publication No. 7-14834 and the Japanese Patent Publication No. 6-322136 are relatively similar to the present invention.
• Viscosity is too low to form a thick film of about 1 to 1000 ⁇ .
• Japan in the organic / inorganic polymer composite and the production method thereof disclosed in JP-A-6-322136 when a highly reactive metal alkoxide is used, it is difficult to control the reactivity and uniformly disperse it. For example, since the sol-gel reaction of titanium alkoxide is very reactive, it tends to have a particle size (> 100 nm) larger than the titanium oxide particles scatter light. Disclosure of the invention
• An object of the present invention is to provide a resin composition capable of forming a transparent, high refractive index and film-like optical member, and a film-like optical member using the same.
• the present inventors can obtain a film-like optical member having a transparent, high refractive index and a desired film thickness by suppressing the reactivity of metal alkoxide in the resin composition and suppressing the particle growth.
• the inventors have found that this is possible and have completed the present invention.
• the present invention is characterized by the following items (1) to (10).
• a resin composition comprising (A) a metal alkoxide, (B) a polymer or oligomer, and / or (C) a reactive monomer, wherein the resin composition comprises at least one component other than the component (A).
• the component has nitrogen atoms, the number of moles of nitrogen atoms in the resin composition is n, and the mass of nitrogen atoms
• the water content of the whole system is 1% by weight
• the resin composition which is the following.
• the (B) polymer or oligomer has no hydroxyl group or carboxynole group, or has a hydroxyl group or carboxynore group and has a nitrogen atom.
• a film-shaped optical member comprising the resin composition according to any one of (1) to (7).
• a resin composition capable of forming an optical member having a desired film thickness that is more transparent and higher in refractive index than before, and an optical member using the same. can be provided.
• the resin composition of the present invention is a resin composition comprising (A) a metal alkoxide, (B) a polymer or oligomer and / or (C) a reactive monomer, wherein the component (A) At least one of the other components has a nitrogen atom, the number of moles of the nitrogen atom in the resin composition is n, the weight of the nitrogen atom is W, the number of moles of the metal alkoxide is n, and the weight of the entire resin composition is When W is set, n / n ⁇ 0.01 and W / W ⁇ 0.001 and the water power S of the whole system is less than L weight%.
• (D) solvents and (E) may contain additives.
• the nitrogen atom has a role of coordinating with the metal alkoxide, controlling the progress of the hydrolysis reaction, and suppressing the growth of the metal oxide particles.
• the amount of nitrogen atoms in the resin composition as described above it is possible to suppress the growth of titanium oxide particles, particularly for titanium alkoxides where hydrolysis reaction is likely to proceed rapidly, and cured products. It becomes possible to make the light scattering of the bow.
• the nitrogen atom in the resin composition contains at least one component other than component (A), that is, (B) a polymer or oligomer, (C) a reactive monomer, (D) a solvent, and (E) an additive. It may be supplied by any component. Considering the stability of the composition and the controllability of the sol-gel reaction in the formation process of the film or cured product, nitrogen atoms obtain a resin film or cured product, as in (B) and (C) components. It is desirable to be supplied with what remains to the end in the system that does not volatilize in the process.
• the metal of the (A) metal alkoxide is not particularly limited, but is preferably a metal selected from Ti, Zn, Zr, La, Th, Ta, and more preferably Ti, Zn, Zr A metal selected from the group consisting of Ti and particularly preferably Ti.
• the hydrolyzable alkoxy group of the (A) metal alkoxide is not particularly limited. For example, methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, pentyloxy group, hexinoreoxy group Etc. If the number of carbons is too small, it becomes difficult to control the sol-gel reaction, and if the number of carbons is too large, the sol-gel reaction proceeds, and therefore, preferably a propoxy group, an isopropoxy group, or a butoxy group, and particularly preferably An isopropoxy group. All of these alkoxy groups on the metal may be the same or different.
• the alkoxide when the metal of the metal alkoxide (A) is titanium is, for example, titanium tetramethoxide, titanium tetraethoxide, titanium tetra-n-propoxide, titanium tetra-iso_propoxide, Titanium tetra_n-butoxide, titanium tetra- sec sec -butoxide, titanium tetra-tert-butoxide, titanium tetrafoxide, etc.
• the (B) polymer or oligomer is not particularly limited, but preferably has a nitrogen atom in its main chain or side chain. Further, those having no hydroxyl group or carboxyl group, or those having a hydroxyl group or carboxyl group and having a nitrogen atom are preferred.
• the sol-gel reaction proceeds rapidly, the polymer composition liquid gels, and the particles scatter light. There is a possibility that it will grow to a certain size.
• the presence of carboxylic acid excessively suppresses the second stage of the sol-gel reaction (the first stage is hydrolysis and the second stage is dehydration condensation), and does not produce a metal oxide, thereby achieving the desired high refractive index. You won't get it.
• Examples of those having a nitrogen atom in the main chain include polyamide, polyurethane, polyurea, polyimine, polyimide, polyamideimide and the like.
• the side chain has a nitrogen atom
• an amide group or an amino group may be substituted as a side chain of polybule, polyacrylol, polyether, polysulfide, polyester, polycarbonate, polyketone or the like.
• the main chain and the side chain may have nitrogen atoms.
• C reaction When a nitrogen atom is supplied to the resin composition by other components such as a functional monomer, (D) solvent, and (E) additive, the polymer or oligomer of (B) does not necessarily need to have a nitrogen atom. ,.
• raw materials for the polyurethane and polyurea include tolylene diisocyanate (TDI), phenolic diisocyanate (PDI), and xylylene diisocyanate (XDI) 1, 6 —Hexamethylene diisocyanate (HMDI), 4, 4'-diphenylmethane diisocyanate (MDI), isophorone diisocyanate (IPDI), tetramethylxylylene diisocyanate (TMXDI) ), Cyclohexanediisocyanate (CHDI), 4,4,1-dicyclohexylenemethane methanediisocyanate (HDCHMDI), and the like, 4, A′-diphenylenomethane diisocyanate, tolylene diisocyanate Aromatic diisocyanates such as cyanate, xylylene diisocyanate, 4, -diphenyl ether diisocyanate, 4,-[2,2_bis
• sulfonates can be exemplified sulfonates, which may be used alone or in combination of two or more kinds.
• a polyisocyanate synthesized in advance may be used, and it may be stabilized with a suitable blocking agent in order to avoid changes over time.
• ethylene glycol for example, ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, neopentyl glycol, dibromonepentyl glycol, 1, 3 propanediol, 1,2 butanediol, 1,3 butanediol, 1,4 butanediol, 1,2 pentanediol, 1,3 pentanediol, 1,2-hexanediol, 1,4 monohexanediol, Addition of aliphatic glycols such as 1,6-hexanediol, 2,3-hexanediol, cyclopentanediol, cyclohexanediol, alicyclic diols such as hydrogenated bisphenol A, and bisphenol A propylene oxide P-xylene Examples include aromatic group-containing
• Examples of materials that can be used as raw materials for the polyamide and polyester include phthalic acid, isophthalic acid, terephthalic acid, tetrahydrophthalic acid, methyltetrahydrophthalic acid, Tylene tetrahydrophthalic acid, hexahydrophthalic acid, adipic acid, sebacic acid, glutaric acid, heptic acid, tetrabromophthalic acid, trimellitic acid, pyromellitic acid, dimer acid, succinic acid, azelaic acid, rosin maleic acid addition Aromatic carboxylic acids such as products, saturated acids, and derivatives thereof such as anhydrides thereof.
• Examples of materials that can be used for the above polyamide, polyamideimide, and polyimide include piperazine, hexamethylenediamine, heptamethylenediamine, tetramethylenediamine, p_xylylenediamine, m _Xylylenediamine, 3_Methylheptamethylenediamine and other aliphatic diamines, 1,3-bis (3-aminophenoxy) benzene, 1,3-bis (4-aminophenoxy) benzene, 1,4-bis (4-Aminophenoxy) benzene, 4, 1 [1,3—Phenylenebis (1-methylethylidene)] bisaniline, 4, A '— [1,4-Phenylenebis (1-methylethylidene)] bisaniline, 3, 3 '— [1,3-Fenylenebis (1-methylethylidene)] bisaniline, 4, 4' —diaminodiphenyl ether, 4,1
• Examples of materials that can be used as the raw material of the polyamideimide include trimellitic acid, 3,3,4'-monobenzophenonetricarboxylic acid, 2,3,3'-diphenyltricarboxylic acid, 3, 6— pyridinetricarboxylic acid, 3, 4, A 'monobenzanilide tricarboxylic acid, 1, 4, 5— naphthalenetricanolevonic acid, 1, 5, 6 _naphthalenetricarboxylic acid, 2 ′ — blackened benzanilide _ 3, 4, 4 ′ —tricarboxylic acid and the like.
• Examples of the reactive derivative of the aromatic tricarboxylic acid include acid anhydrides, halides, esters, amides, ammonium salts, and the like of the aromatic tricarboxylic acid.
• trimellitic anhydride trimellitic anhydride Monochloroide, 1,4-Dicarboxy-3_N, N_dimethylcarbamoylbenzene, 1,4-Dicarbomethoxy_3_carboxybenzene, 1,4_Dicarboxyl 1_Carbophenoxybenzene, 2 , 6-dicarboxy-1-carbomethoxypyridine, 1,6-dicarboxy-1-5 carbamoylnaphthalene, and the like.
• Examples of materials that can be used as the raw material for the polybules and polyacryls include, but are not limited to, bull compounds, acrylic compounds, and methallyl compounds.
• Examples of the Biel compound include styrene, m-methylstyrene, p-methylstyrene, o-methylstyrene, 2,4-dimethylstyrene, 2,5-dimethylstyrene, 3,4-dimethylstyrene, 3 , 5-dimethylstyrene, alkyl styrenes such as p-tert-butylstyrene, p-chlorostyrene, m-chlorostyrene, o-chlorostyrene, p-bromostyrene, m-bromostyrene, o-bromostyrene, p- Halogens such as fluorostyrene, m-fluorostyrene, o-fluorostyrene, o-methyl-p-fluorostyrene, styrenes, vinylbiphenyls such as 4-vinylbiphenyl
• Trialkylstannylmethylbiphenyls such as bulle 4 ′ _trimethylstannylmethylbiphenyl, 4 _bulu 4′-tributylstannylmethylbiphenyl, p-chloroethylenostyrene, m-chloro Halogen-substituted alkyl styrenes such as ethynole styrene and o_chloroethino styrene, p_methoxy styrene, m_methoxy styrene, o-methoxy styrene, p ethoxy styrene, m-ethoxy styrene, o ethoxy styrene, etc.
• Alkoxystyrenes alkoxycarbonylstyrenes such as p-methoxycarbonylstyrene and m-methoxycarbonylstyrene, acyloxystyrenes such as acetyloxystyrene, ethanoloxystyrene and benzoylstyrene, p Alkyl ethers such as vinyl benzyl pour ether Lene, p Alkylsilyl styrenes such as trimethylsilyl styrene, p Trimethylstannyl styrene, p Tributylstannyl styrene, p Alkylstannyl styrenes such as triphenylstannyl styrene, Bierbenzene sulfonic acid ethyl ester, Bierbenyl dimethoxy Fosufaido, vinyl styrenes such as p vinyl-
• the bull compound may be a ⁇ ⁇ ⁇ -substituted maleimide polymer.
• acrylic compound and methacrylic compound examples include cyclopentyl acrylate, cyclohexyl acrylate, methyl cyclohexyl acrylate, trimethyl cyclohexyl acrylate, norbornyl acrylate, norbornyl methyl acrylate, cyano norbornyl acrylate. , Isobornyl acrylate, bornyl acrylate, menthyl acrylate, fentyl acrylate, adamantyl acrylate, dimethyladamantyl acrylate, tricyclo attalinoleate [5. 2. 1.
• diethylene glycol acrylate polyethylene glycol acrylate, polypropylene glycol acrylate, 2-methoxyethyl acrylate, 2-ethoxyformyl acrylate, 2-butoxy acrylate, methoxydiethylene glycol acrylate, methoxy polyethylene Glycol acrylate, dicyclopentenyl oxyalkylate, 2_phenoxy cetyl acrylate, phenoxy diethylene glycol acrylate, phenoxy polyethylene glycol acrylate, 2-benzoyl oxychetyl acrylate , Atylate compounds such as 2-hydroxy_3-phenoxypropyl acrylate, jetylene glycol methacrylate, polyethylene glycol methacrylate, polypropylene glycol Cole metatalylate, 2-Methoxyethyl methacrylate, 2_Ethoxyethyl methacrylate, 2_Butoxychetyl methacrylate, Methoxydiethylene glycol methacrylate, Methylene polyethylene glycol methacrylate
• the nitrogen-containing acrylic polymer is preferably selected from a group containing a functional group such as a secondary amino group, a tertiary amino group, or a nitrogen-containing heterocyclic group.
• a functional group such as a secondary amino group, a tertiary amino group, or a nitrogen-containing heterocyclic group.
• amino (meth) acrylates such as aminoethyl thioaretalate, aminoethyl methacrylate, methylaminoethyl acrylate, methylaminoethyl methacrylate, 2-cyanoethyl acrylate, cyano norbornyl acrylate, Cyan (meth) acrylates such as cyano norbornyl methacrylate, 2-cyanoethyl methacrylate, acrylamide, methacrylamide, ⁇ -methylolacrylamide, ⁇ ethyl acrylamide, ⁇ ⁇ ⁇ methyl methacrylamide, ⁇ -ethyl me
• the component (B) may be an epoxy resin.
• an epoxy resin for example, bisphenol A type epoxy resin [AER-X8501 (Asahi Kasei Kogyo Co., Ltd., trade name), R-301 (oilification shell) Epoxy Co., Ltd., trade name), YL—980 (Oilized Shell Epoxy Co., Ltd., trade name)], Bisphenol F type epoxy resin [YDF—170 (Toto Kasei Co., Ltd., trade name)], Bisphenol AD Type epoxy resin [R_1710 (Mitsui Petrochemical Co., Ltd., trade name)], phenolic novolac type epoxy resin [N—730S (Dainippon Ink Chemical Co., Ltd., trade name), Quatrex _ 2010 (Dow's Chemical Co., Ltd., trade name)], Cresol novolak epoxy resin [YDCN—702S (Toto Kasei Co., Ltd., trade name), EOCN_100 (Nippon Kayaku Co.,
• the blending amount of the component (B) is preferably 0 to 1000 parts by weight with respect to 100 parts by weight of the component (A).
• the (C) reactive monomer is an essential component in a resin composition that is polymerized and cured by heat or light.
• component (C) for example, ionic polymerization or radical polymerization is good.
• Well-known power The present invention is not intended to limit the polymerization form.
• nitrogen atoms are supplied by other components such as (B) polymers or oligomers, (D) solvents, and (E) additives, (C) reactive monomers do not necessarily need to contain nitrogen atoms. .
• Examples of the reactive monomer (C) include urethane acrylate biscoat 831 (trade name, manufactured by Osaka Organic Chemical Industry Co., Ltd.), polyether type urethane acrylate TG B (trade name, manufactured by Kyoeisha Yushi Chemical Co., Ltd.), Urethanes such as polyester type urethane acrylate (D-200A (trade name, manufactured by Kyoeisha Yushi Chemical Co., Ltd.), urethane acrylate photomer 6008 (product name, Sannobu Kone Soil), urethane dialylate chemlink 9503 (trade name, manufactured by Sartoma) Meta) Atalylate, trimethylolpropane ethoxytriatalylate (SR_454, product name manufactured by Sartoma Co., Ltd.), trimethylolpropane propoxytritalylate (R—924, product name manufactured by Nippon Kayaku Co., Ltd.), polyethylene glycol di (meta) Atarylates (those with 2 to 14
• the blending amount of the component (C) is preferably 0 to 1000 parts by weight with respect to 100 parts by weight of the component (A).
• Examples of the solvent (D) include hydrocarbon solvents, ether 'ketone solvents, ester solvents, halogenated hydrocarbons, mineral oils and synthetic oils, animal and vegetable oils, alcohol solvents, and the like. These can be used alone or in combination of two or more. Further, it is preferable to use a solvent having a nitrogen atom.
• hydrocarbon solvent examples include pentane, hexane, heptane, octane, decane, undecane, dodecane, tridecane, tetradecane, hexadecane, isohexane, isooctane, isododecane, naphthene, otaten, cyclopentane, Examples include cyclohexane, cyclopentene, cyclohexene, benzene, ethynolebenzene, tonolene, xylene, styrene, and divinylbenzene.
• ether-ketone solvents examples include acetone, methyl ethyl ketone, methyl isobutanol ketone, cyclohexanone, isophorone, tetrahydrofuran, ethyl ether, isopropyl ether, dioxane, and the like.
• ester solvent examples include ethyl acetate, butyl acetate, isobutyl acetate, and acetate. Mill, octyl acetate, dimethyl phthalate, dimethyl phthalate, dibutyl phthalate, diheptyl phthalate, octyl phthalate, ethyl hexyl phthalate, diisononyl phthalate, octyldecyl phthalate, diisodecyl phthalate, butyl benzyl phthalate, oleate Butylate, Glycerol monooleate, Dibutyl adipate, Dihexyl adipate, Di-2-ethylhexyl adipate, Alkyl adipate, Acetyl noretrietinole citrate, Acetyl tributyl catenate, Jetylhexyl azelate , Dibutyl acetate
• halogenated hydrocarbons examples include methylene chloride, black form, trichloroethane, trichloroethylene, CFC 113, CFC 112, bromopentene, and chlorinated paraffin.
• Examples of the mineral oil and synthetic oil include kerosene, light oil, gasoline, spindle oil, turbine oil, gear oil, machine oil, transformer oil, rubber sol, white sol, mineral turpentine, mineral spirit, and n-paraffin. , Isoparaffin, liquid paraffin, paraffin wax, silicone oil, polybutene, and the like.
• animal and vegetable oils examples include beef tallow, squall, lanolin, soybean oil, coconut oil, rapeseed oil, linseed oil, tung oil, castor oil, and cottonseed oil. These liquids are filtered through silica gel, activated alumina, diatomaceous earth, activated clay, etc. before preparing the catalyst solution. It can be degassed or replaced with an inert gas such as nitrogen or argon.
• Examples of the alcohol solvent include methanol, ethanol, n-propanol, i-propanol, n-butanol, i-butanol, sec-butanol, t-butanol, n-pentanol, i-pentanol, 2 —Methylbutanol, sec-pentanol, t-pentanol, 3-methoxybutanol, n_hexanol, 2-methylpentanol, sec-hexanol, 2-ethylbutanol, sec-heptanol, n_octanol , 2—Echinoré Hexanol, sec octanol, n nonanolenoreconole, n decanol, sec undecyl alcohol, trimethylnonyl alcohol, sec tetradecyl alcohol, se c-heptadecyl alcohol, phenol
• the blending amount of the component (D) is preferably 0 to 1000 parts by weight with respect to 100 parts by weight of the component (A).
• the (E) additive includes a polymerization initiator such as a photoradical polymerization initiator and a thermal radical polymerization initiator, a stabilizer such as an ultraviolet absorber, a light stabilizer, and an antioxidant, and a coupling. Agents, flame retardants and the like.
• thermal radical polymerization initiator examples include 1, 1, 3, 3-tetramethylperoxy 2-ethylenohexanoate, 1, 1-bis (t-butylperoxy) cyclohexane, 1, 1- Bis (t-butylperoxy) cyclododecane, di-t-butylperoxyisophthalate, t-butylperbenzoate, dicumyl peroxide, t-butyltamyl peroxide, 2,5 dimethinole 2,5 di (t-butylperoxy) hexane, 2 , 5 Dimethylolene 2,5-di (t-butylperoxy) hexine, cumene hydride peroxide, methyl ethenole ketone peroxide, methyl isobutyl ketone peroxide, cyclohexanone peroxide, methylcyclohexanone peroxide, acetylacetone Oxide, isobutyno
• Examples of the photo radical polymerization initiator include benzophenone, N, ⁇ '-tetramethylolene, 4-diaminobenzophenone (Michler's ketone), ⁇ , ⁇ tetramethyl-1,4'A'- diaminebenzophenone, 4 Aromatic ketones such as methoxy monodimethylamino benzophenone, 2-ethylenethraquinone and phenanthrenequinone, benzoin ethers such as benzoin methyl ether, benzoin ethyl ether and benzoin phenyl ether, methyl benzoin and ethyl benzoin Benzyl derivatives such as benzoin and benzyl dimethyl ketal, 2— ( ⁇ ⁇ u ⁇ u ⁇ uyl) 4, 4,5 diphenylimidazolnimer, 2— ( ⁇ ⁇ ⁇ ⁇ u ⁇ u ⁇ yl) 4, 4,5 ((m —Met
• the blending amount of these radical polymerization initiators is preferably in the range of 0.1 to 10 parts by weight with respect to 100 parts by weight of the total amount of components (B) and (C). More preferably, it is in the range of ⁇ 5 parts by weight.
• Examples of the ultraviolet absorber include salicylic acid ultraviolet absorbers such as phenyl salicylate and para-butylphenyl salicylate, 2, 4 dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2, Benzophenone UV absorbers such as 2'-dihydroxy-4, ⁇ '-dimethyoxybenzophenone, 2 _ (2 '—hydroxy-methylphenyl) benzotriazole, 2 _ (2' —hydroxy 1 3 ', 5' —di 1 t-b Tilphenyl) benzotriazole 2- (2 '—hydroxyl 3', 5 '—di-t-amyl benzoyl) benzotriazole-based UV-absorbing lj, 2 _ethylyl xyl-2-cyanol 1,3 ; —Diphenyl acrylate, ethyl 2-cyanol 3, 3 ′ — Cyanacrylate UV such as diphenyl acrylate The power of
• Examples of the light stabilizer include bis (2,2,6,6-tetramethyl_4-piperidyl) sebacate, bis (1,2,2,6,6_pentamethyl_4-piperidininole). Sebacate, dimethyl succinate 1- (2 hydroxyethyl) 4 Hydro 1, 2, 2, 6, 6 Tetramethyl piperidine polycondensate and other hindered amine light stabilizers include force S, limited to these It is not something.
• the ultraviolet absorber and the light stabilizer can be usually added in the range of 0.05 to 20 parts by weight with respect to 100 parts by weight of the total amount of the components (B) and (C).
• antioxidants examples include quinones such as parabenzoquinone, tolquinone, and naphthoquinone, hydroquinones such as hydroquinone, para-t-butylcatechol, and 2,5-di-t-butyl hydroquinone, di-t-butyl 'para-cresol hydroquinone monomethyl.
• Quaternaries such as ethers, pyrogallol and other phenols, copper salts such as copper naphthenate and copper otate, trimethylbenzylammonium chloride, trimethylbenzylammonium maleate, phenyltrimethylammonium chloride
• examples include ammonium salts, oximes such as quinone dioxymethyl methyl ketyl oxime, amine hydrochlorides such as triethylamine hydrochloride and dibutyramine hydrochloride, oils such as mineral oil, essential oil, fatty oil, and the like. Limited Not.
• the antioxidant is added in various types and amounts depending on conditions such as compatibility with the filler, desired molding workability, and resin storage stability. Usually, the total amount of component (B) and component (C) 10 to 10 parts per million by weight.
• the coupling agent is not particularly limited, but a silane coupling agent is preferable.
• This silane coupling agent is usually Y (Si) X (Y is a monovalent group having a functional group and bonded to Si, X is a monovalent group having hydrolyzability and bonded to Si) It is represented by The functional group of Y in the above formula includes, for example, bur, ami-epoxy, black mouth, mercapto, methacryloxy, cyan, rubamate, pyridine, sulfonyl azide, urea, styryl, chloromethinole, ammonium salt, alcohol, etc. The group of is mentioned.
• Examples of X include chloro, methoxy, ethoxy, methoxyethoxy and the like. Specific examples include butyltrimethoxysilane, buturetris (2-methoxyethoxy) silane, ⁇ - (2-aminoethyl)
• the coupling agent is usually added in an amount of 0.001 to 5 parts by weight based on 100 parts by weight of the total amount of the component (i) and the component (C).
• Examples of the flame retardant include hexabromobenzene, tetrabromobisphenol A, decabromodiphenyl oxide, tribromophenol, dibromophenyl daricidyl ether, perchloropentacyclodecane, and a heptanoic acid derivative. And the like, and these may be used alone or in combination of two or more. Further, phosphoric acid compounds such as tris phosphate (diclonal propyl) and tris phosphate (dibromopropyl), boric acid compounds and the like can be used in combination.
• antimony trioxide, iron oxide, aluminum hydride, and the like as auxiliary flame retardants can be used in combination with flame retardants to further enhance the flame retardant effect.
• the halogen-based flame retardant is 1 to 50 parts by weight with respect to 100 parts by weight of the total amount of the component (B) and the component (C)
• the auxiliary flame retardant such as antimony trioxide is 1 to 15 parts by weight. Used in a range.
• commercially available hydrates such as aluminum hydroxide and magnesium hydroxide can be used as fillers for flame retardancy.
• the amount added is 100 parts by weight of the total amount of component (B) and component (C). However, it is preferably used in the range of 10 to 300 parts by weight.
• the resin composition of the present invention comprises the above-described component (A), component (B) and / or component (C) as essential components, and other components added as necessary with ordinary resins. It can be obtained by stirring and mixing as in the case of the composition. It should be noted that the point requiring attention at this time is the mixing of water, and the water content in the resin composition is preferably 1% by weight or less. Therefore, it is desirable that the mixing and stirring be performed in a closed system.
• the film-like optical member of the present invention can be obtained, for example, by applying the resin composition of the present invention on a substrate, drying it, and curing it if necessary.
• the method for applying the resin composition on the substrate is not particularly limited, and examples thereof include brush coating, spin coating, spraying, slit coater, gravure printing, and screen printing.
• examples of the substrate include a glass plate, a plastic plate, a plastic film, and a solar battery cell.
• the drying performed after the application of the resin composition is not limited as long as the solvent in the film is sufficiently volatilized, but the method and conditions are not particularly limited.
• the reaction can be carried out in the range of 50 to 150 ° C, more preferably 60 to 80 ° C. If the drying temperature is less than 50 ° C, drying of component (D) may be insufficient, and if it exceeds 150 ° C, component (C) may volatilize and a good cured film can be obtained. Tend to be difficult.
• curing after drying may be performed by appropriately determining the curing temperature and time depending on the component and blending amount, but preferably at a temperature of 130 to 200 ° C for 2 to Carrying heat for 60 minutes, more preferably 130 to 200 ° C. for 2 to 30 minutes. If this caloric heat is less than 130 ° C, there is a risk that sufficient curing cannot be performed. Also, there is no particular limitation when the resin composition is a photo-curing compound, but it is preferable to use a high-pressure mercury lamp or the like and expose it to 100-200 OmjZcm 2 to be finally cured.
• the film thickness of the film-shaped optical member of the present invention is easily formed to a desired thickness by adjusting the viscosity of the resin composition of the present invention or by appropriately selecting the film forming means and its conditions. It is possible. For example, if the blending amount of the solvent as component (D) is reduced, the viscosity of the resin composition increases and it becomes easier to form a relatively thick optical member, and the blending amount of component (D) is increased. As a result, the viscosity of the resin composition decreases, and it becomes easier to form a relatively thin optical member. The In addition, when a spin coating method is applied as a resin composition coating means, the ability to form a relatively thick optical member by decreasing the number of rotations or increasing the number of coatings.
• the refractive index of the film-like optical member of the present invention is preferably 1.8 or more.
• toluene is used as a polymerization solvent in a 4 liter stainless steel autoclave with a pressure resistance of 2.3 kg / cm3 ⁇ 4, 1, 2, 2, 6, 6, —pentamethinore 4-piperidinoremethacrylate relay MFA—711MM, Hitachi 500 g (made by Kasei Kogyo Co., Ltd.) was weighed. Then, nitrogen gas is passed at room temperature for about 1 hour to replace dissolved oxygen, the inside of the autoclave is pressurized and sealed, and the temperature is raised to 60 ° C. Then, azobisisoptilo is used as a polymerization initiator.
• L-4 was synthesized in the same manner as described above using L-3 with toluene as the methyl ethyl ketone. Moreover, the place which uses FA-711MM in the synthesis
• combination of said L-3 used what used dimethylamino ethino rare talirate (DE, the product made by Kojin Co., Ltd.), and synthesize
• DE dimethylamino ethino rare talirate
• each resin composition is appropriately diluted with a solvent, and this is diluted on each of a silicon wafer (refractive index measurement) and glass (for absorbance measurement) cut into approximately 25 mm squares.
• the resin composition with thermosetting compound was further cured on a hot plate at 150 ° C. for 10 minutes.
• the thickness of the sample film used for the refractive index measurement is 0.01 to 0.2 ⁇ , and the thickness of the sample film used for the absorbance measurement is 1 to 20 ⁇ .
• Each sample film thus obtained was subjected to refractive index measurement and absorbance measurement.
• the refractive index was measured using an ellipsometer (633 nm), and the absorbance was measured using a UV spectrophotometer U-3310 manufactured by Hitachi High-Tech, Inc. in the range of 450 nm.
• the absorbance was measured as the absorbance per unit thickness by measuring the membrane thickness using a stylus-type thickness meter Solan Dektak.
• TiOiPr Titanium tetraisopropoxide
• Pitzkor K-30 Polybulol pyrrolidone (Daiichi Kogyo Seiyaku Co., Ltd.)
• Pitzkor K-90 Polybulol pyrrolidone (Daiichi Kogyo Seiyaku Co., Ltd.)
• L-3 FA-711MM acrylic homopolymer (TLS70 weight 0/0 included)
• D-2 DE acrylic homopolymer (oligomer, TLS80 weight 0/0 included)
• LH-2 tBAEM (Dedasa Japan Co., Ltd., 2_t_butylaminoethyl metatalylate, Bottom 1 ⁇ 70 wt% included)
• LH-3 FA-712HM (Hankuri manufactured by Hitachi Chemical Co., Ltd., tetramethylpiperidyl methacrylate, including 1 ⁇ 70% by weight)
• PMMA polymethyl methacrylate Tari rate (TLS90 weight 0/0 included)
• LC1_0 FA-711MM / HEMA ( TLS70 weight 0/0 included)
• FA-711MM Funkrill, pentamethylpiperidylmetatalylate manufactured by Hitachi Chemical Co., Ltd.
• ACM ⁇ Akkuro Morpholine, manufactured by Kojinsha
• IB-XA Osaka Organic Chemical Co., Ltd., Isobonyl Atarylate
• Trigonox 22-70E manufactured by Kayaku Akuzo, 1,1-di (t_butylperoxy) cyclohexane
• A-714 Nijunika's silane coupling agent

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• Organic Chemistry (AREA)
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Citations (5)

• 2005
  • 2005-07-29 JP JP2005221910A patent/JP2008255124A/ja active Pending
• 2006
  • 2006-06-13 WO PCT/JP2006/311820 patent/WO2007013230A1/ja not_active Ceased
  • 2006-06-15 TW TW095121431A patent/TW200706589A/zh not_active IP Right Cessation

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