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WO2014168108A1 - Composition de résine contenant un composé fluoré, corps moulé, agent d'ajustement de la dispersion des longueurs d'onde, et procédé d'ajustement de la dispersion des longueurs d'onde d'une résine - Google Patents

Composition de résine contenant un composé fluoré, corps moulé, agent d'ajustement de la dispersion des longueurs d'onde, et procédé d'ajustement de la dispersion des longueurs d'onde d'une résine Download PDF

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Publication number
WO2014168108A1
WO2014168108A1 PCT/JP2014/060081 JP2014060081W WO2014168108A1 WO 2014168108 A1 WO2014168108 A1 WO 2014168108A1 JP 2014060081 W JP2014060081 W JP 2014060081W WO 2014168108 A1 WO2014168108 A1 WO 2014168108A1
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WO
WIPO (PCT)
Prior art keywords
group
resin
bis
fluorene
epoxy compound
Prior art date
Application number
PCT/JP2014/060081
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English (en)
Japanese (ja)
Inventor
一史 高野
小林　綾子
祐輝 大内
信輔 宮内
山田　昌宏
大策 荘所
完爾 若林
中嶋　孝宏
Original Assignee
大阪ガスケミカル株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 大阪ガスケミカル株式会社 filed Critical 大阪ガスケミカル株式会社
Priority to KR1020157027936A priority Critical patent/KR20150142682A/ko
Priority to JP2015511249A priority patent/JPWO2014168108A1/ja
Priority to CN201480018415.XA priority patent/CN105308122A/zh
Publication of WO2014168108A1 publication Critical patent/WO2014168108A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/62—Alcohols or phenols
    • 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
    • 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
    • C08K5/15—Heterocyclic compounds having oxygen in the ring
    • C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
    • C08K5/1515—Three-membered rings
    • 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
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/37—Thiols

Definitions

  • the present invention relates to a resin composition containing a compound having a fluorene skeleton (9,9-bisarylfluorene skeleton), a molded product thereof, a wavelength dispersion adjusting agent, and a resin wavelength dispersion adjusting method.
  • a compound having a fluorene skeleton (such as a 9,9-bisphenylfluorene skeleton) is known to have excellent functions such as a high refractive index and high heat resistance.
  • fluorene compounds having a reactive group such as bisphenol fluorene (BPF), biscresol fluorene
  • BPF bisphenol fluorene
  • BCF bisphenoxyethanol fluorene
  • BPEF bisphenoxyethanol fluorene
  • Patent Document 1 discloses a molding material composed of a polyester resin having a 9,9-bisphenylfluorene skeleton.
  • Patent Document 2 discloses a polyurethane resin having a 9,9-bisphenylfluorene skeleton and crosslinked with a crosslinking agent.
  • 9,9-bis (4-hydroxyphenyl) fluorene or 9,9-bis [4- (2-hydroxyethoxy) phenyl] fluorene (bisphenoxyethanol) is used as a part of the diol component constituting the resin. Fluorene skeleton is introduced into the resin.
  • Patent Document 3 discloses a resin composition comprising a compound having a 9,9-bisphenylfluorene skeleton and a thermoplastic resin. This document describes that a compound having a 9,9-bisphenylfluorene skeleton can be added to a thermoplastic resin to impart a high refractive index to the thermoplastic resin.
  • a transparent resin film is prepared by mixing 30 to 40 parts by weight of a specific compound (bisphenol fluorenediglycidyl ether, bisphenoxyethanol fluorene or bisphenoxyethanol fluoredenyl acrylate) with 100 parts by weight of a polycarbonate resin. And that the refractive index has increased.
  • a specific compound bisphenol fluorenediglycidyl ether, bisphenoxyethanol fluorene or bisphenoxyethanol fluoredenyl acrylate
  • Patent Document 4 discloses an optical resin composition composed of a transparent resin and a fluorene compound having a 9,9-bisarylfluorene skeleton. And this document describes that the birefringence can be reduced without impairing the mechanical properties and heat resistance of the transparent resin, and in a specific example, the fluorene-containing polyester resin is compared with the polycarbonate resin.
  • Patent Document 5 discloses that a phenol compound functions as a nucleating agent ( ⁇ crystal nucleating agent) for forming a ⁇ crystal structure in a crystalline resin such as polylactic acid.
  • ⁇ crystal nucleating agent a nucleating agent for forming a ⁇ crystal structure in a crystalline resin such as polylactic acid.
  • ⁇ crystal nucleating agent a nucleating agent for forming a ⁇ crystal structure in a crystalline resin such as polylactic acid.
  • 1 to 5% by weight of 9,9-bis (4-hydroxy-3-methylphenyl) fluorene was added to the ⁇ -crystal (melting point: 168 ° C.) poly-L lactic acid and melted. Kneading to obtain poly L-lactic acid in which ⁇ crystals (melting point: 163 ° C.) were formed, and Tg was changed from 56.5 ° C. to 60.9-62.1 ° C. as the crystal structure was changed. It is described that changed.
  • JP 2012-211252 A discloses a film containing a cellulose derivative (such as cellulose triacetate) and a fluorene compound having a 9,9-bisarylfluorene skeleton (such as bisphenoxyethanol fluorene). ing. And in the Example of this document, it is described that the retardation value of the stretched film containing cellulose triacetate and bisphenoxyethanol fluorene was 0 or a negative value.
  • JP 2002-284864 A (Claims, Examples) JP 2002-284834 A (Claims, Examples) Japanese Patent Laying-Open No. 2005-162785 (Claims and Examples) JP 2011-8017 A (Claims, Examples) Japanese Patent Laying-Open No. 2011-21083 (Claims and Examples) JP 2012-211252 A (Claims, Examples)
  • Another object of the present invention is to provide a resin composition to which a compound having a fluorene skeleton can be added without impairing mechanical strength, a molded article formed with this resin composition, a wavelength dispersion adjusting agent, and a resin wavelength dispersion adjusting method. Is to provide.
  • Still another object of the present invention is to provide a resin composition capable of adjusting or controlling wavelength dispersibility, a molded article formed from the resin composition, a wavelength dispersion adjusting agent, and a resin wavelength dispersion adjusting method.
  • the present inventors surprisingly have a compound in which a compound having a fluorene skeleton has a reverse wavelength dispersibility (or negative wavelength dispersibility, a phase difference (or birefringence) that increases as the wavelength increases) with respect to the resin. ) Can be imparted (or expressed).
  • resins especially thermoplastic resins.
  • the wavelength dispersion of the resin can be reduced (or adjusted to low wavelength dispersion)]
  • the present invention has been completed.
  • the resin composition of the present invention includes a non-epoxy resin, a non-epoxy compound having a 9,9-bisarylfluorene skeleton, and an epoxy compound.
  • the non-epoxy compound having a 9,9-bisarylfluorene skeleton may be, for example, a compound represented by the following formula (1).
  • ring Z is an aromatic hydrocarbon ring, R 1 and R 2 are substituents, X is a group — [(OR 3 ) nY] (wherein Y is a hydroxyl group, a mercapto group, or A (meth) acryloyloxy group, R 3 is an alkylene group, n is an integer of 0 or more) or an amino group, k is an integer of 0 to 4, m is an integer of 0 or more, and p is an integer of 1 or more] .
  • non-epoxy compound having a 9,9-bisarylfluorene skeleton may be a compound represented by the following formula (1A).
  • the ring Z may be a benzene ring or a naphthalene ring
  • R 1 may be an alkyl group
  • k may be 0 to 1
  • R 2 may be It may be an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group or an alkoxy group
  • m may be 0 to 2
  • R 3 may be a C 2-4 alkylene group
  • n is 0 May be 2 and p may be 1 to 3.
  • Non-epoxy compounds having a 9,9-bisarylfluorene skeleton typically include 9,9-bis (hydroxyphenyl) fluorene, 9,9-bis (alkyl-hydroxyphenyl) fluorene, and 9,9-bis.
  • (Aryl-hydroxyphenyl) fluorene 9,9-bis (di or trihydroxyphenyl) fluorene, 9,9-bis (hydroxynaphthyl) fluorene, 9,9-bis (hydroxyalkoxyphenyl) fluorene, 9,9-bis It may be at least one selected from (alkyl-hydroxyalkoxyphenyl) fluorene, 9,9-bis (aryl-hydroxyalkoxyphenyl) fluorene, and 9,9-bis (hydroxyalkoxynaphthyl) fluorene.
  • the non-epoxy resin may be a thermoplastic resin, and in particular, may be at least one selected from a cyclic olefin resin, a methacrylic resin, an aromatic polycarbonate resin, an aromatic polyester resin, and a cellulose derivative.
  • the epoxy compound may particularly contain at least a polyfunctional epoxy compound.
  • the ratio of each component to 100 parts by weight of the non-epoxy resin is, for example, that the ratio of the non-epoxy compound having a 9,9-bisarylfluorene skeleton is about 0.5 to 50 parts by weight.
  • the ratio of the epoxy compound may be about 0.1 to 30 parts by weight.
  • the proportion of the epoxy compound may be, for example, about 1 to 100 parts by weight with respect to 100 parts by weight of the non-epoxy compound having a 9,9-bisarylfluorene skeleton. .
  • the present invention also includes a molded body formed from the resin composition.
  • a molded article may be an optical molded article [such as an optical film (such as a retardation film)].
  • the molded body of the present invention may be a film (film-shaped molded body), and such a molded body may be a stretched film.
  • the wavelength dispersion of the non-epoxy resin is adjusted or controlled by adding a non-epoxy compound having a 9,9-bisarylfluorene skeleton to the non-epoxy resin in combination with the epoxy compound ( For example, the wavelength dispersion can be reduced).
  • the present invention relates to an additive for adjusting or controlling (for example, reducing) the wavelength dispersion of a non-epoxy resin, and a non-epoxy compound having an 9,9-bisarylfluorene skeleton and an epoxy compound Are also included (for example, a wavelength dispersion reducing agent).
  • a wavelength dispersion adjusting agent for example, a wavelength dispersion reducing agent
  • a method of adjusting the wavelength dispersion of the resin is also included.
  • the ratio of each component and the use ratio with respect to resin are the same as in the resin composition.
  • the wavelength range for adjusting the dispersibility is not particularly limited.
  • the visible light range is about 300 to 800 nm (for example, 350 to 770 nm), preferably about 400 to 750 nm (for example, 400 to 700 nm). Also good.
  • 9,9-bis (hydroxyaryl) fluorenes and “9,9-bis (hydroxy (poly) alkoxyaryl) fluorenes” mean “9,9-bis (hydroxyaryl)”. As long as it has “) fluorene skeleton” or “9,9-bis (hydroxy (poly) alkoxyaryl) fluorene skeleton”, it includes compounds having substituents on aryl groups and fluorene skeletons (specifically, positions 2 to 7 of fluorene) Use for meaning.
  • 9,9-bis (hydroxy (poly) alkoxyaryl) fluorene means 9,9-bis (hydroxyalkoxyaryl) fluorene and 9,9-bis (hydroxypolyalkoxyaryl) fluorene. Used to mean including
  • the resin composition of the present invention is a novel resin composition containing a compound (non-epoxy compound) having a fluorene skeleton (9,9-bisarylfluorene skeleton).
  • a resin composition has resin characteristics according to the type of resin (non-epoxy resin), and also conventionally known effects obtained by adding a compound having a fluorene skeleton (improvement of refractive index, reduction of birefringence) , Improvement of stretchability, etc.) can be obtained.
  • a resin composition contains a compound having a fluorene skeleton which is a low molecule, but does not impair the mechanical properties, in particular, a compound having only a fluorene skeleton. Compared with the case of containing, the mechanical properties can be further improved or improved, so that it is very useful.
  • the compound having a fluorene skeleton seems to be able to impart reverse wavelength dispersion to the resin.
  • the wavelength dispersion is adjusted or Can be controlled.
  • the addition of a compound having a fluorene skeleton imparts reverse wavelength dispersibility to the resin, but when combined with an epoxy compound, the wavelength dispersibility becomes uniform, or a low wavelength dispersible resin (composition Product) can be easily obtained.
  • the resin composition of the present invention comprises a non-epoxy resin (hereinafter sometimes referred to simply as a resin) and a non-epoxy compound having a 9,9-bisarylfluorene skeleton (hereinafter sometimes referred to as a fluorene compound). And an epoxy compound.
  • a non-epoxy resin hereinafter sometimes referred to simply as a resin
  • a non-epoxy compound having a 9,9-bisarylfluorene skeleton hereinafter sometimes referred to as a fluorene compound
  • resin a wide range of resins can be used (or applied), and any of a thermoplastic resin and a curable resin (thermal or photo-curable resin) may be used.
  • thermoplastic resin examples include olefin resin ⁇ eg, chain olefin resin [ethylene resin (eg, polyethylene), propylene resin (eg, polypropylene), polymethylpentene, etc.], cyclic olefin resin, etc. ⁇ , halogen-containing resin) Vinyl resins (polyvinyl chloride, fluororesins, etc.), vinyl resins (eg, polyvinyl alcohol, acrylonitrile resins), acrylic resins (eg, methacrylic resins such as polymethyl methacrylate), styrene resins [eg, styrene Monomers or copolymers of polystyrene monomers (polystyrene, styrene- ⁇ -methylstyrene copolymer, etc.), copolymers of styrene monomers and copolymerizable monomers (styrene-acrylonitrile copolymers ( AS resin), styrene
  • polylactic acid, etc. aromatic polyester resin, etc.] polyacetal resin, polyamide resin (for example, aliphatic polyamide resin such as polyamide 6, polyamide 66, polyamide 610, polyamide 11, polyamide 12, polyamide 612, polyamide 6/66; Aromatic polyamide resins such as polyamide MXD), polyphenylene ether resins, polysulfone resins, polyphenylene sulfide resins, polyimide resins, polyether ketone resins, cellulose derivatives, and thermoplastic elastomers. And so on.
  • polyamide resin for example, aliphatic polyamide resin such as polyamide 6, polyamide 66, polyamide 610, polyamide 11, polyamide 12, polyamide 612, polyamide 6/66; Aromatic polyamide resins such as polyamide MXD), polyphenylene ether resins, polysulfone resins, polyphenylene sulfide resins, polyimide resins, polyether ketone resins, cellulose derivatives, and thermoplastic elast
  • Resins may be used alone or in combination of two or more.
  • the molecular weight of the thermoplastic resin can be selected according to the type of the resin.
  • the number average molecular weight can be selected from a range of 2000 or more (for example, 3000 or more), 5000 or more (for example, 8000 to 1000000), preferably May be 10,000 or more (for example, 12,000 to 800,000), more preferably 15,000 or more (for example, 20,000 to 500,000).
  • the molecular weight can be measured in terms of polystyrene by a conventional method such as gel permeation chromatography (GPC).
  • curable resin examples include acrylic resin (thermal or photocurable resin, non-epoxy curable resin), acrylic resin (thermal or photocurable acrylic resin), phenol resin, amino resin (urea resin, melamine resin, etc.). ), Furan resins, unsaturated polyester resins, thermosetting urethane resins, silicone resins, thermosetting polyimide resins, diallyl phthalate resins, vinyl ester resins, and the like.
  • the curable resins may be used alone or in combination of two or more.
  • the curable resin may contain a curing agent, a curing accelerator, or the like depending on the type.
  • Resins may be used alone or in combination of two or more.
  • the resin may be either a crystalline resin or an amorphous resin.
  • the resin may be a resin having a positive wavelength dispersion or a resin having a negative wavelength dispersion (reverse wavelength dispersion).
  • the resin may typically be a thermoplastic resin.
  • the resin may be a resin having excellent transparency, for example, a cyclic olefin resin, a methacrylic resin, an aromatic polycarbonate resin, an aromatic polyester resin, a cellulose derivative, or the like.
  • Cyclic olefin resin is resin which uses cyclic olefin as a polymerization component at least.
  • the cyclic olefin may be a monocyclic olefin or a polycyclic olefin.
  • the cyclic olefin includes a substituent such as a hydrocarbon group [eg, an alkyl group (eg, a C 1-10 alkyl group such as a methyl group, preferably a C 1-5 alkyl group), a cycloalkyl group (eg, cyclohexyl group).
  • a C 5-10 cycloalkyl group such as a group), an aryl group (eg, a C 6-10 aryl group such as a phenyl group), an alkenyl group (eg, a C 2-10 alkenyl group such as a propenyl group), a cycloalkenyl group (For example, C 5-10 cycloalkenyl group such as cyclopentenyl group, cyclohexenyl group, etc.), alkylidene group (eg, C 2-10 alkylidene group such as ethylidene group, preferably C 2-5 alkylidene group, etc.) , polar group [e.g., alkoxy groups (e.g., C 1-10 alkoxy group such as methoxy group, preferred Ku is C 1-6 alkoxy group), an acyl group (e.g., a C 2-5 alkanoyl group such as acetyl group), an acyloxy group [e.
  • cyclic olefins include monocyclic olefins [eg, cycloalkenes (eg, cycloC 3-10 alkenes such as cyclobutene, cyclopentene, cycloheptene, cyclooctene, etc.), cycloalkadienes (eg, cyclopentadiene, etc.
  • cycloalkenes eg, cycloC 3-10 alkenes such as cyclobutene, cyclopentene, cycloheptene, cyclooctene, etc.
  • cycloalkadienes eg, cyclopentadiene, etc.
  • bicyclic olefins ⁇ eg norbornenes [eg norbornene (eg 2-norbornene), alkyl norbornene (eg 5-methyl-2-norbornene, 5, 5 or 5,6-dimethyl-2-norbornene, 5-ethylidene-2-norbornene), aryl norbornene (eg, 5-phenyl-2-norbornene), norbornene having a polar group (eg, 5-cyano-2-norbornene, etc.) Cyanonorbornene Acyloxynorbornene such as 5-methoxycarbonyl-2-norbornene, 5-methyl-5-methoxycarbonyl-2-norbornene, 5,6-dimethoxycarbonyl-2-norbornene, 5-methyl-5-cyclohexyloxycarbonyl-2-norbornene (Alkoxycarbonyl norbornene,
  • Acyloxynorbornadiene (such as alkoxycarbonylnorbornadiene); haloalkylnorbornadiene such as 5,6-di (trifluoromethyl) -2,5-norbornadiene; oxonorbornadiene such as 7-oxo-2-norbornadiene)], tricyclic olefin ⁇
  • tricycloalkenes eg, C 6-25 tricycloalkenes such as dihydrodicyclopentadienes (such as dihydrodicyclopentadiene)]
  • tricycloalkadienes eg, Dicyclopentadiene (dicyclopentadiene, methyldicyclopentadiene, etc.), tricyclo [4.4.0.1 2,5 ] undeca-3,7-diene, tricyclo [4.4.0.1 2,5 ]
  • a C 6-25 tricycloalkadiene such as undeca-3,8-diene, etc.]
  • cyclic olefins e.g., hexa cycloalkenes (e.g., hexacyclo [6.6.1.1 3,6 .0 2,7 .0 9,14] -4- heptadecene C such as 12-40 Hexacycloalkene) and the like ⁇ and the like.
  • the cyclic olefin resin may be a cyclic olefin homopolymer or a copolymer (for example, a copolymer of a monocyclic olefin and a polycyclic olefin, a copolymer of a plurality of polycyclic olefins, etc.), or cyclic.
  • a copolymer of an olefin and a copolymerizable monomer may be used.
  • Examples of the copolymerizable monomer include a chain olefin [alkene (eg, ethylene, propylene, 1-butene, 1-pentene, 1-hexene, 3-methyl-1-butene, 2-methyl-1-pentene).
  • alkene eg, ethylene, propylene, 1-butene, 1-pentene, 1-hexene, 3-methyl-1-butene, 2-methyl-1-pentene.
  • 3-ethyl-1-pentene 4-methyl-1-pentene, 4-methyl-1-hexene, 4,4-dimethyl-1-hexene, 4,4-dimethyl-1-pentene, 4-ethyl-1 C 2-20 alkenes such as -hexene, 3-ethyl-1-hexene, 1-octene, 1-decene, 1-dodecene, 1-tetradecene, 1-hexadecene, 1-octadecene, 1-eicocene), alkadienes (for example , 1,4-hexadiene, 4-methyl-1,4-hexadiene, 5-methyl-1,4-hexadiene, 1,7-nonconjugated C 5-20 a such octadiene Cadien etc.), polymerizable nitrile compounds (eg (meth) acrylonitrile etc.), (meth) acrylic monomers (eg (meth) acrylic acid such as methyl
  • the ratio of cyclic olefin is, for example, 10 mol% or more (for example, 20 mol) with respect to the total amount of cyclic olefin and copolymerizable monomer. % Or more), preferably 30 mol% or more, more preferably 40 mol% or more.
  • Preferred cyclic olefin resins include cyclic olefin copolymers ⁇ eg, cyclic olefins (eg, cyclic olefins containing at least norbornenes) and copolymerizable monomers [eg, chain olefins (eg, C 2 ⁇ Copolymer) with a copolymerizable monomer containing at least 6 alkene).
  • cyclic olefin copolymers eg, cyclic olefins (eg, cyclic olefins containing at least norbornenes) and copolymerizable monomers [eg, chain olefins (eg, C 2 ⁇ Copolymer) with a copolymerizable monomer containing at least 6 alkene).
  • a cyclic olefin copolymer having a polar group for example, a cyclic olefin having a polar group ⁇ eg, norbornene having a polar group [eg, acyloxynorbornene (eg, 5-methoxycarbonyl-2 An alkoxycarbonyl group such as norbornene or 5-methyl-5-methoxycarbonyl-2-norbornene (eg, norbornene substituted with a C 1-10 alkoxycarbonyl group, preferably a C 1-4 alkoxycarbonyl group), etc.]
  • a copolymerizable monomer for example, a copolymerizable monomer [for example, a copolymerizable monomer containing at least a chain olefin (eg, C 2-6 alkene such as ethylene)] is preferable. .
  • the ratio of the cyclic olefin having a polar group to the whole cyclic olefin is, for example, 10 mol% or more, preferably 20 mol% or more, more preferably 30 mol% or more. May be.
  • the cyclic olefin resins may be used alone or in combination of two or more.
  • the methacrylic resin examples include resins having at least a methacrylic acid ester as a polymerization component.
  • the methacrylic resin is an alkyl methacrylate [for example, an alkyl methacrylate ester (for example, a C 1-20 alkyl methacrylate such as methyl methacrylate, ethyl methacrylate, propyl methacrylate, butyl methacrylate, 2-ethylhexyl methacrylate,
  • the alkyl methacrylates may be used alone or in combination of two or more.
  • Specific methacrylic resins include alkyl methacrylates (especially alkyl methacrylates containing at least methyl methacrylate) homopolymers or copolymers, alkyl methacrylates (particularly alkyl methacrylates containing at least methyl methacrylate) and copolymers. And a copolymer with a functional monomer.
  • the copolymerizable monomer is not particularly limited as long as it is copolymerizable.
  • a (meth) acrylic monomer ⁇ for example, (meth) acrylic acid, alkyl acrylate (for example, methyl acrylate, ethyl acrylate) C 1-10 alkyl acrylates such as propyl acrylate and butyl acrylate), alicyclic (meth) acrylates (eg, (meth) acrylic acid C 5-10 cycloalkyl esters such as cyclohexyl (meth) acrylate; Decalinyl (meth) acrylate, norbornyl (meth) acrylate, bornyl (meth) acrylate, bi to tetracycloalkyl (meth) acrylate such as adamantyl (meth) acrylate, etc.], hydroxyalkyl (meth) acrylate [for example, (meth) acrylic Acid hydroxyethyl etc.
  • an alkane diol di (meth) acrylate e.g., ethylene glycol di (meth) acrylate, diethylene glycol di ( (Meth) acrylate, tetraethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, etc.
  • alkanetriol di to tri (meth) acrylate for example, trimethylolethane tri (meth) acrylate, trimethylolpropane tri ( Meth) acrylates
  • polyols such as alkanetetraol di to tetra (meth) acrylates (pentaerythritol tetra (meth) acrylate etc.), poly (meth) acrylates, polyols Alkylene oxide (e.g., C 2-4 alkylene
  • Preferred methacrylic resins include resins having methyl methacrylate as a polymerization component, such as polymethyl methacrylate, copolymers having methyl methacrylate as a polymerization component [for example, copolymers of methyl methacrylate and alkyl methacrylate esters. (For example, methyl methacrylate-methacrylic acid C 2-8 alkyl ester copolymer) and the like].
  • the proportion of methyl methacrylate is determined based on the total amount of monomers [methyl methacrylate and other monomers (methacrylic acid C 2-8 alkyl ester, copolymerizable monomer). Body etc.)], for example, about 55 to 99.9% by weight, preferably 60% or more (for example, about 65 to 99% by weight), more preferably 70% or more (for example, 75%). Or about 95% by weight).
  • Aromaatic polycarbonate resin examples include resins having an aromatic diol and a carbonate-forming compound as polymerization components.
  • aromatic diol examples include bisphenols and dihydroxyarene (hydroquinone, resorcinol, etc.).
  • bisphenols include dihydroxyarenes [eg, di ( hydroxyC 6-10 arenes) such as 4,4′-dihydroxybiphenyl], bis (hydroxyphenyl) alkanes [eg, bis (4-hydroxyphenyl) methane 1,1-bis (4-hydroxyphenyl) ethane, 1,1-bis (4-hydroxyphenyl) -1-phenylethane, 2,2-bis (4-hydroxyphenyl) propane, 2,2-bis ( 4-hydroxy-3-methylphenyl) propane, 2,2-bis (4-hydroxy-3-isopropylphenyl) propane, 2,2-bis (3-tert-butyl-4-hydroxyphenyl) propane, 2,2 -Bis (4-hydroxyphenyl) butane, 2,2-bis (4-hydroxyphenyl) octane, 2,2 Bis (3-bromo-4-hydroxyphenyl) propane, 2,2-bis
  • aromatic diols in particular, bis (hydroxyphenyl) alkanes [especially bis (hydroxyphenyl) C 1-4 alkanes such as 2,2-bis (4-hydroxyphenyl) propane], bis (hydroxyphenyl) Bisphenols such as -alkyl) arenes [bis (hydroxyphenyl-C 1-4 alkyl) benzene etc.] are preferred.
  • Aromatic diols may be used alone or in combination of two or more.
  • Examples of the carbonate-forming compound include carbonates such as phosgene (phosgene, diphosgene, triphosgene, etc.), carbonates [eg, dialkyl carbonate (dimethyl carbonate, diethyl carbonate, etc.), diaryl carbonate (diphenyl carbonate, dinaphthyl carbonate, etc.). Diesters] and the like. Among these, phosgene, diphenyl carbonate and the like may be preferably used.
  • the carbonate-forming compounds may be used alone or in combination of two or more.
  • the aromatic polycarbonate resin may be used alone or in combination of two or more.
  • aromatic polyester resins include polyalkylene arylate resins, polyarylate resins [for example, aromatic dicarboxylic acids (such as terephthalic acid) and aromatic diols (biphenol, bisphenol A, xylylene glycol, alkylene oxide adducts thereof, etc.) And the like)], and liquid crystalline polyester resins.
  • polyalkylene arylate resin examples include polyalkylene terephthalate resin [for example, polyalkylene terephthalate (eg, poly C 2-4 alkylene terephthalate such as polyethylene terephthalate, polypropylene terephthalate, polybutylene terephthalate), alkylene terephthalate unit (polyalkylene terephthalate unit) ), Polyalkylene naphthalate resin [for example, polyalkylene naphthalate (for example, poly C 2-4 alkylene naphthalate such as polyethylene naphthalate), alkylene naphthalate unit (polyalkylene naphthalate unit) Having a copolyester], polycycloalkane dialkylene terephthalate resin [for example, polycycloalkanedia Sharp emission terephthalate (e.g., poly cyclohexane dimethylene terephthalate), such as a copolyester having cycloalkan
  • the copolymer component includes, for example, a diol component [eg, alkane diol (eg, C 2-6 alkane diol such as ethylene glycol, propylene glycol, butane diol, hexane diol), polyalkane diol (eg, diethylene glycol).
  • alkane diol eg, C 2-6 alkane diol such as ethylene glycol, propylene glycol, butane diol, hexane diol
  • polyalkane diol eg, diethylene glycol
  • Di-hexaC 2-4 alkanediols such as polytetramethylene glycol), alicyclic diols (eg 1,4-cyclohexanedimethanol etc.), aromatic diols (eg C 2-4 alkylenes of bisphenols) Oxide adducts, etc.)], dicarboxylic acid components ⁇ eg aliphatic dicarboxylic acids (eg C 4-12 alkane dicarboxylic acids such as glutaric acid, adipic acid, sebacic acid), aromatic dicarboxylic acids [eg asymmetric aromatics] Zika Rubonic acid (eg phthalic acid, isophthalic acid etc.), diphenyldicarboxylic acid etc.] ⁇ , hydroxycarboxylic acid component (eg hydroxybenzoic acid etc.) and the like.
  • the copolymerization components may be used alone or in combination of two or more.
  • the proportion of alkylene arylate units may be, for example, 40% by weight or more, preferably 50% by weight or more.
  • the aromatic polyester resin may be crystalline or non-crystalline.
  • the aromatic polyester resin may have a linear structure or a branched structure.
  • Aromatic polyester resins may be used alone or in combination of two or more.
  • the cellulose derivative is not particularly limited, and various cellulose derivatives such as cellulose ester, cellulose carbamate (for example, cellulose phenyl carbamate), cellulose ether and the like can be used.
  • cellulose ester examples include cellulose acetate such as cellulose diacetate (DAC) and cellulose triacetate (TAC); cellulose C 3-5 acylate such as cellulose propionate and cellulose butyrate; cellulose acetate propionate (CAP), And cellulose acylate such as cellulose acetate C 3-5 acylate such as cellulose acetate butyrate (CAB).
  • DAC cellulose diacetate
  • TAC cellulose triacetate
  • cellulose C 3-5 acylate such as cellulose propionate and cellulose butyrate
  • CAP cellulose acetate propionate
  • CAB cellulose acetate butyrate
  • cellulose ether examples include alkyl celluloses (eg, C 1-4 alkyl celluloses such as methyl cellulose and ethyl cellulose), hydroxyalkyl celluloses (eg, hydroxy C 2 ⁇ such as hydroxyethyl cellulose (HEC) and hydroxypropyl cellulose (HPC)).
  • alkyl celluloses eg, C 1-4 alkyl celluloses such as methyl cellulose and ethyl cellulose
  • hydroxyalkyl celluloses eg, hydroxy C 2 ⁇ such as hydroxyethyl cellulose (HEC) and hydroxypropyl cellulose (HPC)
  • hydroxyalkylalkyl cellulose eg, hydroxy C 2-4 alkyl C 1-4 alkyl cellulose such as hydroxypropylmethyl cellulose
  • carboxyalkyl cellulose such as carboxymethyl cellulose (CMC)
  • alkyl-carboxyalkyl cellulose Such as methyl carboxymethyl cellulose
  • carboxymethyl cellulose sodium CMC salts such as alkali metal salts
  • cellulose esters and cellulose ethers are preferable, and cellulose esters (cellulose acylates) such as cellulose acetate and cellulose acetate C 3-4 acylate are particularly preferable. More specifically, cellulose esters such as cellulose diacetate, cellulose triacetate, cellulose acetate propionate, and cellulose acetate butyrate may be suitably used as the cellulose derivative.
  • the cellulose derivatives may be used alone or in combination of two or more.
  • the fluorene compound only needs to have a 9,9-bisarylfluorene skeleton, such as a compound having no reactive group [for example, 9,9-bisarylfluorene (for example, 9,9-bisphenylfluorene), etc.
  • a compound having no reactive group for example, 9,9-bisarylfluorene (for example, 9,9-bisphenylfluorene), etc.
  • a compound in which p is 0 in formula (1) described later] may be used, but usually has a reactive group.
  • the reactive group examples include non-epoxy reactive groups such as a hydroxyl group, a mercapto group, a carboxyl group, an amino group, and a (meth) acryloyloxy group.
  • the fluorene compound may have these reactive groups singly or in combination of two or more.
  • the reactive group may be directly bonded to 9,9-bisarylfluorene, or may be bonded via an appropriate linking group (for example, a (poly) oxyalkylene group).
  • fluorene compound examples include a compound represented by the following formula (1).
  • ring Z is an aromatic hydrocarbon ring, R 1 and R 2 are substituents, X is a group — [(OR 3 ) nY] (wherein Y is a hydroxyl group, a mercapto group, or A (meth) acryloyloxy group, R 3 is an alkylene group, n is an integer of 0 or more) or an amino group, k is an integer of 0 to 4, m is an integer of 0 or more, and p is an integer of 1 or more] .
  • examples of the aromatic hydrocarbon ring represented by the ring Z include a benzene ring, a condensed polycyclic aromatic hydrocarbon ring [for example, a condensed bicyclic hydrocarbon (for example, indene, naphthalene, etc. Condensed bicyclic to tetracyclic hydrocarbons such as C 8-20 condensed bicyclic hydrocarbons, preferably C 10-16 condensed bicyclic hydrocarbons), condensed tricyclic hydrocarbons (eg anthracene, phenanthrene, etc.), etc.
  • a condensed polycyclic aromatic hydrocarbon ring for example, a condensed bicyclic hydrocarbon (for example, indene, naphthalene, etc. Condensed bicyclic to tetracyclic hydrocarbons such as C 8-20 condensed bicyclic hydrocarbons, preferably C 10-16 condensed bicyclic hydrocarbons), condensed tricyclic hydrocarbons (eg anthracene, phen
  • a ring assembly hydrocarbon ring (bi or ter C 6-10 arene ring such as biphenyl ring, terphenyl ring or binaphthyl ring).
  • the two rings Z may be the same or different rings, and may usually be the same ring.
  • Preferred rings Z include a benzene ring, a naphthalene ring, and a biphenyl ring, and may be a benzene ring.
  • examples of the group R 1 include a cyano group, a halogen atom (a fluorine atom, a chlorine atom, a bromine atom, etc.), a hydrocarbon group [eg, an alkyl group, an aryl group (C 6 such as a phenyl group). -10 aryl group) and the like] and acyl groups (for example, alkylcarbonyl groups such as methylcarbonyl, ethylcarbonyl, pentylcarbonyl, etc.) and the like, and in particular, alkyl groups are often used.
  • a cyano group e.g, an alkyl group, an aryl group (C 6 such as a phenyl group). -10 aryl group) and the like
  • acyl groups for example, alkylcarbonyl groups such as methylcarbonyl, ethylcarbonyl, pentylcarbonyl, etc.
  • alkyl group examples include C 1-12 alkyl groups such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, and a t-butyl group (for example, a C 1-8 alkyl group, particularly a C 1-1 such as a methyl group). 4 alkyl group) and the like.
  • k is plural (2 to 4)
  • the types of the plural groups R 1 may be the same or different from each other.
  • the kind of group R ⁇ 1 > substituted by the different benzene ring may be the same or different.
  • the bonding position (substitution position) of the group R 1 is not particularly limited, and examples thereof include the 2nd, 7th, 2nd and 7th positions of the fluorene ring.
  • the preferred substitution number k is 0 to 1, in particular 0.
  • the two substitution numbers k may be the same or different.
  • the substituent R 2 substituted on the ring Z is usually a non-reactive substituent, for example, an alkyl group (eg, a C 1-12 alkyl group such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, C 1-8 alkyl group etc.), cycloalkyl group (C 5-8 cycloalkyl group such as cyclohexyl group), aryl group (eg phenyl group, tolyl group, xylyl group, naphthyl group etc.) Hydrocarbon groups such as 6-10 aryl groups), aralkyl groups (C 6-10 aryl-C 1-4 alkyl groups such as benzyl and phenethyl groups); alkoxy groups (C 1 such as methoxy groups and ethoxy groups) -8 an alkoxy group), such as C 5-10 cycloalkyl group such as a cycloalkoxy group
  • a group such as an alkylthio group such as a C 1-8 alkylthio group such as a methylthio group) —SR (wherein R is as defined above); an acyl group (such as a C 1-6 acyl group such as an acetyl group); Alkoxycarbonyl group (C 1-4 alkoxy-carbonyl group such as methoxycarbonyl group); halogen atom (fluorine atom, chlorine atom, bromine atom, iodine atom etc.); nitro group; cyano group; substituted amino group (for example, dimethyl group) And a dialkylamino group such as an amino group).
  • R is as defined above
  • an acyl group such as a C 1-6 acyl group such as an acetyl group
  • Alkoxycarbonyl group C 1-4 alkoxy-carbonyl group such as methoxycarbonyl group
  • halogen atom fluorine atom, chlorine atom, bromine atom,
  • Preferred groups R 2 include hydrocarbon groups [eg, alkyl groups (eg, C 1-6 alkyl groups), cycloalkyl groups (eg, C 5-8 cycloalkyl groups), aryl groups (eg, C 6-10 Aryl group), aralkyl group (for example, C 6-8 aryl-C 1-2 alkyl group and the like), alkoxy group (C 1-4 alkoxy group and the like) and the like.
  • Further preferred groups R 2 include an alkyl group [C 1-4 alkyl group (particularly methyl group) and the like], an aryl group [eg C 6-10 aryl group (particularly phenyl group) and the like] and the like.
  • the group R 2 may form the ring assembly hydrocarbon ring together with the ring Z.
  • the types of the groups R 2 may be the same or different from each other.
  • the type of the group R 2 may be the same or different.
  • the number of substitutions m can be selected according to the type of the ring Z, and may be, for example, 0 to 8, preferably 0 to 4 (eg, 0 to 3), and more preferably 0 to 2.
  • the number of substitutions m may be the same or different from each other, and may usually be the same.
  • examples of the alkylene group represented by the group R 3 include C 2-6 alkylene such as ethylene group, propylene group, trimethylene group, 1,2-butanediyl group, and tetramethylene group.
  • a group preferably a C 2-4 alkylene group, and more preferably a C 2-3 alkylene group.
  • the type of alkylene group may be composed of different alkylene groups, and may be generally composed of the same alkylene group.
  • the types of the groups R 3 may be the same or different, and may be usually the same.
  • the number (addition mole number) n of oxyalkylene groups (OR 3 ) may be 0 or more (for example, 0 to 20), for example, 0 to 15 (for example, 1 to 12), preferably 0 to 10 ( For example, it may be 1 to 6), more preferably 0 to 4 (eg 1 to 4), particularly 0 to 2 (eg 0 to 1). Further, depending on the type of resin, there may be a case where a remarkable improvement effect is obtained when n is 0 or when n is 1 or more. Therefore, either a compound in which n is 0 or a compound in which n is 1 or more may be selected depending on the type of resin. The number of substitutions n may be the same or different for different rings Z.
  • Preferred X is a group — [(OR 3 ) nY], and particularly Y is preferably a hydroxyl group.
  • the compound whose Y is a hydroxyl group is represented by following formula (1A).
  • the substitution number p of the group X may be 1 or more (for example, 1 to 6), for example, 1 to 4, preferably 1 to 3, more preferably 1 to 2, particularly 1.
  • the substitution number p may be the same or different in each ring Z, and is usually the same in many cases.
  • the substitution position of the group X is not particularly limited, and it may be substituted at an appropriate substitution position on the ring Z.
  • the group X may be substituted at the 2-6 position of the phenyl group, and may preferably be substituted at the 4 position.
  • the group X is a hydrocarbon ring different from the hydrocarbon ring bonded to the 9-position of fluorene in the condensed polycyclic hydrocarbon ring (for example, naphthalene
  • the ring is substituted at least on the 5th and 6th positions of the ring.
  • Specific fluorene compounds include 9,9-bis (hydroxyaryl) fluorenes [or 9,9-bis (hydroxyaryl) fluorene skeletons.
  • X is a group in the formula (1), such as - [(OR 3) n- OH] , compound; this In al compounds, hydroxyl group, and the like mercapto group, or
  • the 9,9-bis (hydroxyphenyl) fluorenes include, for example, 9,9-bis (hydroxyphenyl) fluorene [for example, 9,9-bis (4-hydroxyphenyl) fluorene], 9,9-bis (alkyl 9,9-bis such as 9,9-bis (4-hydroxy-3-methylphenyl) fluorene, 9,9-bis (4-hydroxy-3,5-dimethylphenyl) fluorene (Mono or di C 1-4 alkyl-hydroxyphenyl) fluorene], 9,9-bis (aryl-hydroxyphenyl) fluorene [eg, 9,9-bis (4-hydroxy-3-phenylphenyl) fluorene, etc.
  • the 9,9-bis (hydroxynaphthyl) fluorenes correspond to the 9,9-bis (hydroxyphenyl) fluorenes, and are compounds in which the phenyl group is substituted with a naphthyl group, for example, 9,9-bis ( Hydroxynaphthyl) fluorene [eg, 9,9-bis (6-hydroxy-2-naphthyl) fluorene, 9,9-bis (5-hydroxy-1-naphthyl) fluorene] and the like.
  • 9,9-bis ( Hydroxynaphthyl) fluorene eg, 9,9-bis (6-hydroxy-2-naphthyl) fluorene, 9,9-bis (5-hydroxy-1-naphthyl) fluorene
  • 9,9-bis (hydroxy (poly) alkoxyphenyl) fluorenes include, for example, 9,9-bis (hydroxyalkoxyphenyl) fluorene ⁇ eg, 9,9-bis [4- (2-hydroxyethoxy) phenyl] fluorene, 9,9-bis [4- (2-hydroxypropoxy) phenyl] fluorene such as 9,9-bis (hydroxy C 2-4 alkoxyphenyl) fluorene ⁇ , 9,9-bis (alkyl - hydroxy alkoxyphenyl) Fluorene ⁇ eg, 9,9-bis [4- (2-hydroxyethoxy) -3-methylphenyl] fluorene, 9,9-bis [4- (2-hydroxypropoxy) -3-methylphenyl] fluorene, Such as 9-bis [4- (2-hydroxyethoxy) -3,5-dimethylphenyl] fluorene 9,9-bis (mono or di C 1-4 alkyl-hydroxy C 2-4 alkoxy
  • 9,9-bis (hydroxy (poly) alkoxynaphthyl) fluorenes compounds corresponding to the 9,9-bis (hydroxy (poly) alkoxyphenyl) fluorenes, wherein a phenyl group is substituted with a naphthyl group
  • 9,9-bis (hydroxyalkoxynaphthyl) fluorene ⁇ eg, 9,9-bis [6- (2-hydroxyethoxy) -2-naphthyl] fluorene, 9,9-bis [6- (2-hydroxypropoxy) 9,9-bis (hydroxyalkoxynaphthyl) fluorenes such as 9,9-bis (hydroxyC 2-4 alkoxynaphthyl) fluorene ⁇ such as) -2-naphthyl] fluorene.
  • 9,9-bis (hydroxyphenyl) fluorene 9,9-bis (alkyl-hydroxyphenyl) fluorene [for example, 9,9-bis (mono or di C 1-4 alkyl- Hydroxyphenyl) fluorene], 9,9-bis (aryl-hydroxyphenyl) fluorene [eg, 9,9-bis (mono or diC 6-10 aryl-hydroxyphenyl) fluorene], 9,9-bis (di or A compound in which n is 0 in the above formula (1A) such as trihydroxyphenyl) fluorene and 9,9-bis (hydroxynaphthyl) fluorene; 9,9-bis (hydroxyalkoxyphenyl) fluorene ⁇ eg, 9,9-bis (hydroxy C 2-4 alkoxyphenyl) fluorene ⁇ , 9,9-bis (alkyl - hydroxy alkoxyphenyl) fluorene ⁇ e.g., 9,9-bis (hydroxyphenyl) fluorene
  • n is 1 or more (for example, 1 to 4, preferably 1 to 2, more preferably 1) in the above formula (1A) such as -4alkoxynaphthyl) fluorene ⁇ is preferable.
  • 9,9-bis (hydroxyalkoxyphenyl) fluorene such as 9,9-bis (hydroxyethoxyphenyl) fluorene may be used from the standpoint that the effect of homogenizing wavelength dispersion by the epoxy compound appears remarkably.
  • Fluorene compounds may be used alone or in combination of two or more.
  • the ratio of the fluorene compound can be selected, for example, from the range of about 0.1 parts by weight or more (for example, 0.2 to 200 parts by weight) with respect to 100 parts by weight of the resin. It may be 0.5 to 80 parts by weight, more preferably about 1 to 50 parts by weight, usually 0.5 to 50 parts by weight (for example, 0.5 to 40 parts by weight, preferably 0.7 to 30 parts by weight). Parts, more preferably 1 to 20 parts by weight, particularly 2 to 18 parts by weight, particularly preferably 3 to 15 parts by weight). In particular, since the effect of homogenizing the wavelength dispersion by the epoxy compound appears remarkably, the ratio of the fluorene compound is 5 to 15 parts by weight (particularly 8 to 13 parts by weight) with respect to 100 parts by weight of the resin. Good.
  • the proportion of the fluorene compound used is 20 parts by weight or less (for example, 0.1 to 18 parts by weight), preferably 15 parts by weight or less (for example, 0.2 to 12 parts by weight) with respect to 100 parts by weight of the resin. Part), more preferably 10 parts by weight or less (for example, 0.3 to 7 parts by weight), particularly 5 parts by weight or less (for example, 0.5 to 5 parts by weight).
  • the resin properties can often be maintained or improved at a high level even if a relatively large proportion of the fluorene compound is added. Therefore, the proportion of the fluorene compound used is 20 parts by weight or more (for example, 20 to 100 parts by weight), preferably 25 parts by weight or more (for example, 25 to 80 parts by weight), more preferably 100 parts by weight of the resin. It may be 30 parts by weight or more (for example, 30 to 70 parts by weight).
  • the epoxy compound (or epoxy resin) can be roughly classified into a monofunctional epoxy compound (monofunctional epoxy compound) and a polyfunctional epoxy compound (polyfunctional epoxy compound).
  • monofunctional epoxy compounds include glycidyl ethers (monoglycidyl ether) [eg, alkyl glycidyl ether (eg, 2-ethylhexyl glycidyl ether), alkenyl glycidyl ether (eg, allyl glycidyl ether), aryl glycidyl ether, etc.
  • polyfunctional epoxy compound examples include diglycidyl ether, alkanediol diglycidyl ether (for example, C 2-10 alkane such as butanediol diglycidyl ether, neopentyl glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether).
  • alkanediol diglycidyl ether for example, C 2-10 alkane such as butanediol diglycidyl ether, neopentyl glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether.
  • Diol diglycidyl ether Diol diglycidyl ether
  • polyalkane diol diglycidyl ether eg, poly C 2-4 alkane diaudiglycidyl ether such as polypropylene glycol diglycidyl ether
  • cycloalkane dialkanol diglycidyl ether eg cyclohexane dimethanol diglycidyl ether
  • Glycidyl ethers [for example, di- or triglycidyls of C 3-10 alkanetri- or tetraols such as di- to hexa-glycidyl ethers of alkane tri to hexaols (eg trimethylolpropane di or triglycidyl ethers, glycerin
  • (Glycidyloxy) naphthalene bis (2-glycidyl Jill oxy naphthyl) diglycidyl sulfopropyl such as bis (glycidyloxy naphthyl) C 1-6 alkanes such as methane, binding these di (glycidyloxy) naphthalenes directly or Tetraglycidyl ether (eg bis [2,7-di (glycidyloxy) naphthyl] methane etc.) linked via a linking group (eg alkylene group such as methylene group, ethylene group or alkylidene group)], Glycidyl ether type epoxy compounds such as glycidyl ether compounds having a xanthene skeleton (for example, 9-phenyl-2,7-diglycidyloxy-1,3,4,5,6,8-hexamethylxanthene); glycidyl ester type Epoxy compounds [eg aromatic dica Boric acid (
  • the polyfunctional epoxy compound (particularly, glycidyl ether type epoxy compound) includes an epoxy compound having a fluorene skeleton (polyfunctional epoxy compound).
  • the epoxy compound having a fluorene skeleton include a compound represented by the following formula (1B) (that is, a compound in which Y is a glycidyloxy group in X of the formula (1)).
  • Specific epoxy compounds having a fluorene skeleton include 9,9-bis (glycidyloxyaryl) fluorenes [or 9,9-bis (glycidyloxyaryl) fluorenes.
  • 9,9-bis (glycidyloxyphenyl) fluorenes include, for example, 9,9-bis (glycidyloxyphenyl) fluorene [eg, 9,9-bis (4-glycidyloxyphenyl) fluorene], 9,9- Bis (alkyl-glycidyloxyphenyl) fluorene [eg, 9,9-bis (4-glycidyloxy-3-methylphenyl) fluorene, 9,9-bis (4-glycidyloxy-3,5-dimethylphenyl) fluorene, etc.
  • 9,9-bis (mono- or di-C 1-4 alkyl-glycidyloxyphenyl) fluorene]
  • 9,9-bis (aryl-glycidyloxyphenyl) fluorene for example, 9,9-bis (4-glycidyloxy- 9,9-bis such as 3-phenylphenyl) fluorene (mono- or di-C 6-10 ants Ru-glycidyloxyphenyl) fluorene]
  • 9,9-bis (polyglycidyloxyphenyl) fluorene eg, 9,9-bis (3,4-diglycidyloxyphenyl) fluorene, 9,9-bis (2,4 9,9-bis (di- or triglycidyloxyphenyl) fluorene such as -diglycidyloxyphenyl) fluorene].
  • the 9,9-bis (glycidyloxynaphthyl) fluorenes correspond to the 9,9-bis (glycidyloxyphenyl) fluorenes and are compounds in which a phenyl group is substituted with a naphthyl group, such as 9,9- Bis (glycidyloxynaphthyl) fluorene [eg, 9,9-bis (6-glycidyloxy-2-naphthyl) fluorene, 9,9-bis (5-glycidyloxy-1-naphthyl) fluorene] and the like.
  • 9,9- Bis (glycidyloxynaphthyl) fluorene eg, 9,9-bis (6-glycidyloxy-2-naphthyl) fluorene, 9,9-bis (5-glycidyloxy-1-naphthyl) fluorene
  • 9,9-bis (glycidyloxy (poly) alkoxyphenyl) fluorenes include, for example, 9,9-bis (glycidyloxyalkoxyphenyl) fluorene ⁇ eg, 9,9-bis [4- (2-glycidyloxyethoxy) ) Phenyl] fluorene, 9,9-bis [4- (2-glycidyloxypropoxy) phenyl] fluorene and other 9,9-bis (glycidyloxy C 2-4 alkoxyphenyl) fluorene ⁇ , 9,9-bis (alkyl) -Glycidyloxyalkoxyphenyl) fluorene ⁇ eg, 9,9-bis [4- (2-glycidyloxyethoxy) -3-methylphenyl] fluorene, 9,9-bis [4- (2-glycidyloxypropoxy) -3 -Methylphenyl] fluorene, 9,9-bis [4- (2
  • the 9,9-bis (glycidyloxy (poly) alkoxynaphthyl) fluorenes correspond to the 9,9-bis (glycidyloxy (poly) alkoxyphenyl) fluorenes, and the phenyl group is substituted with a naphthyl group.
  • the multifunctional epoxy compounds may be used alone or in combination of two or more.
  • the epoxy compounds may be used alone or in combination of two or more.
  • the epoxy compound may contain at least a polyfunctional epoxy compound.
  • an epoxy compound may be comprised only with a polyfunctional epoxy compound, and may combine a polyfunctional epoxy compound and a monofunctional epoxy compound.
  • the epoxy compound may be solid or liquid at normal temperature (eg, about 15 to 25 ° C.).
  • the viscosity (25 ° C.) of the liquid epoxy compound may be, for example, 1 to 6000 mPa ⁇ s, preferably 10 to 4000 mPa ⁇ s, more preferably about 50 to 2000 mPa ⁇ s, and 1000 mPa ⁇ s or less.
  • An epoxy compound having a low viscosity of for example, 1 to 500 mPa ⁇ s, preferably 300 mPa ⁇ s or less (eg 50 to 200 mPa ⁇ s), more preferably 150 mPa ⁇ s or less (eg 70 to 140 mPa ⁇ s)] May be used.
  • the proportion of the epoxy compound can be selected from the range of, for example, about 0.05 parts by weight or more (for example, 0.07 to 100 parts by weight) with respect to 100 parts by weight of the resin. It may be about 0.3 to 50 parts by weight, more preferably about 0.5 to 40 parts by weight, usually 0.1 to 30 parts by weight (eg, 0.3 to 25 parts by weight, preferably 0.5 to 20 parts by weight, more preferably 0.7 to 15 parts by weight, particularly 0.8 to 10 parts by weight, particularly preferably 1 to 5 parts by weight.
  • the ratio of the epoxy compound is, for example, 0.1 to 200 parts by weight (eg 0.5 to 150 parts by weight), preferably 1 to 100 parts by weight (eg 2 to 2 parts by weight) with respect to 100 parts by weight of the fluorene compound. 80 parts by weight), more preferably 3 to 60 parts by weight, particularly about 5 to 40 parts by weight, usually 1 to 100 parts by weight (eg 2 to 80 parts by weight, preferably 3 to 50 parts by weight, More preferably, it may be about 5 to 30 parts by weight, particularly 8 to 25 parts by weight.
  • the resin composition of the present invention may contain other additives ⁇ additives that are neither a fluorene compound nor an epoxy compound, for example, a filler or a reinforcing agent, a colorant (dye pigment), a conductive agent, if necessary.
  • additives may be used alone or in combination of two or more.
  • the ratio of another additive can be suitably selected according to the kind.
  • the proportion of the stabilizer is about 0.001 to 10 parts by weight, preferably 0.01 to 7 parts by weight, more preferably about 0.05 to 5 parts by weight with respect to 100 parts by weight of the thermoplastic resin. Also good.
  • the resin composition can be obtained by mixing a resin, a fluorene compound, and an epoxy compound [further, with other components (such as other additives) as necessary].
  • the mixing method is not particularly limited, and may be mixed by, for example, melt kneading or may be mixed by dissolving each component in a solvent.
  • the present invention also includes a molded body formed of such a resin composition.
  • the shape of such a molded body is not particularly limited, and can be appropriately selected depending on the application. For example, a two-dimensional structure (film shape, sheet shape, plate shape, etc.), a three-dimensional structure (tubular, rod shape, tube) Shape, hollow shape, etc.).
  • the resin composition of the present invention is often excellent in optical properties, and an optical material or an optical molded body (in particular, an optical film, an optical lens, etc.) may be suitably formed.
  • the molded body can be manufactured using, for example, an injection molding method, an injection compression molding method, an extrusion molding method, a transfer molding method, a blow molding method, a pressure molding method, a casting molding method, and the like.
  • the resin composition of the present invention is often excellent in various optical properties and is useful for forming a film (particularly an optical film). Therefore, the present invention also includes a film (such as an optical film) formed from the resin composition.
  • the thickness of the film can be selected from the range of about 1 to 1000 ⁇ m according to the application, and may be, for example, 1 to 200 ⁇ m, preferably 5 to 150 ⁇ m, and more preferably about 10 to 120 ⁇ m.
  • Such a film (such as an optical film) is formed by forming (or molding) the resin composition using a conventional film forming method, casting method (solvent casting method), melt extrusion method, calendar method, or the like. Can be manufactured.
  • the film may be a stretched film.
  • a stretched film may be either a uniaxially stretched film or a biaxially stretched film.
  • the stretching ratio may be about 1.05 to 10 times (for example, 1.1 to 5 times) in each direction in uniaxial stretching or biaxial stretching, and is usually 1.1 to 3 times (for example, 1. 2 to 2.5 times).
  • biaxial stretching it may be equal stretching or partial stretching.
  • uniaxial stretching longitudinal stretching or lateral stretching may be used.
  • the thickness of the stretched film may be, for example, about 1 to 150 ⁇ m, preferably 3 to 120 ⁇ m, and more preferably about 5 to 100 ⁇ m.
  • Such a stretched film can be obtained by subjecting a film after film formation (or an unstretched film) to a stretching treatment.
  • the stretching method is not particularly limited. In the case of uniaxial stretching, a wet stretching method or a dry stretching method may be used. In the case of biaxial stretching, a tenter method (also referred to as a flat method), a tube method, or the like may be used. Good.
  • Tear strength A tear test was performed using a digital Elmendorf tear tester SA-WP (manufactured by Toyo Seiki Seisakusho). The sample used was a 75 mm ⁇ 63 mm rectangular sample (conforming to JISK7128-2) with a 20 mm cut in the center, and the obtained results were converted to tear strength per 30 ⁇ m.
  • the retardation of the film was measured with a high-speed retardation measuring device RE-100 manufactured by Otsuka Electronics Co., Ltd. Moreover, (the retardation value at each wavelength and N 400, N 589, N 700 ) in evaluating the wavelength dispersion, the 400 nm, 589 nm, measurement of retardation values of 700 nm.
  • the ratio of hindered phenolic antioxidant was 2000 ppm with respect to the total amount of TAC and BPEF, and the ratio of phosphorus antioxidant was 1000 ppm with respect to the total amount of TAC and BPEF.
  • the resin composition was transparent and was mixed uniformly.
  • the obtained resin composition was melt-pressed (hot pressed) using a press molding machine to obtain a film (unstretched film).
  • the tear strength of the film was 0.11 N
  • the yield strength was 71.6 MPa
  • the elongation at break was 9.9%.
  • the phase difference (N 400 ) at a wavelength of 400 nm is 0.12 nm
  • the phase difference (N 589 ) at a wavelength of 589 nm is 0.21 nm
  • the haze of the film was 0.9, and the total light transmittance was 92%.
  • Example 1 In Reference Example 1, a resin composition was obtained in the same manner as in Reference Example 1 except that 1.6 parts by weight of an epoxy compound (trimethylolpropane triglycidyl ether) was further melt-kneaded. In addition, the resin composition was transparent and was mixed uniformly.
  • an epoxy compound trimethylolpropane triglycidyl ether
  • the tear strength is 0.13 N
  • the yield point strength is 79.8 MPa
  • the elongation at break is 11.2%
  • the phase difference (N 400 ) at a wavelength of 400 nm is 0.16 nm
  • the phase difference (N 589 ) at a wavelength of 589 nm is 0.15 nm
  • the phase difference (N 700 ) at a wavelength of 700 nm is 0.15 nm
  • the haze was 0.6 and the total light transmittance was 92%.
  • Example 2 Reference Example 1 and Reference Example 1 except that 2.0 parts by weight of 9,9-bis (4-glycidyloxyphenyl) fluorene (Osaka Gas Chemical Co., Ltd.) were melt-kneaded as an epoxy compound. Similarly, a resin composition was obtained. In addition, the resin composition was transparent and was mixed uniformly.
  • the tear strength is 0.12 N
  • the yield point strength is 77.4 MPa
  • the elongation at break is 12.9%, confirming that the mechanical properties are greatly improved as compared with Reference Example 1. did.
  • the retardation (N 400 ) at a wavelength of 400 nm is 0.21 nm
  • the retardation (N 589 ) at a wavelength of 589 nm is 0.20 nm
  • the retardation (N 700 ) at a wavelength of 700 nm is 0.20 nm
  • the haze was 1.2 and the total light transmittance was 92%.
  • the tear strength of the film was 0.38 N
  • the yield strength was 63.7 MPa
  • the elongation at break was 2.8%.
  • a phase difference at a wavelength of 400 nm (N 400) is 4.70Nm
  • the phase difference at a wavelength of 589 nm (N 589) is 5.08Nm
  • the phase difference at a wavelength 700 nm (N 700 ) was 5.18 nm
  • the haze of the film was 0.9, and the total light transmittance was 92%.
  • Example 3 In Reference Example 2, a resin composition was obtained in the same manner as in Reference Example 2 except that 1.6 parts by weight of an epoxy compound (trimethylolpropane triglycidyl ether) was further melt-kneaded. In addition, the resin composition was transparent and was mixed uniformly.
  • an epoxy compound trimethylolpropane triglycidyl ether
  • the tear strength is 0.58 N
  • the yield point strength is 67.4 MPa
  • the elongation at break is 5.7%
  • the phase difference (N 400 ) at a wavelength of 400 nm is 4.43 nm
  • the phase difference (N 598 ) at a wavelength of 589 nm is 4.59 nm
  • the phase difference (N 700 ) at a wavelength of 700 nm is 4.63 nm
  • N 400 / N 589 0.96
  • N 700 / N 589 1.01).
  • the haze was 0.6 and the total light transmittance was 92%.
  • Reference Example 3 In Reference Example 1, 11 parts by weight of BPEF was replaced with 18 parts by weight of 9,9-bis [4- (2-hydroxyethoxy) -3-phenylphenyl] fluorene (Osaka Gas Chemical Co., Ltd., hereinafter referred to as BOPPEF). Except for the above, a film (unstretched film) was obtained in the same manner as in Reference Example 1. The cylinder temperature was 210 to 280 ° C. And various characteristics were measured using the obtained film.
  • the tear strength of the film was 0.41 N
  • the yield strength was 68.0 MPa
  • the elongation at break was 4.5%.
  • the retardation at a wavelength of 400 nm was 4.66 nm
  • the retardation at a wavelength of 589 nm was 5.79 nm
  • the haze of the film was 0.9, and the total light transmittance was 92%.
  • Example 4 In Reference Example 3, a resin composition was obtained in the same manner as in Reference Example 3, except that 1.6 parts by weight of an epoxy compound (trimethylolpropane triglycidyl ether) was further melt-kneaded. In addition, the resin composition was transparent and was mixed uniformly.
  • an epoxy compound trimethylolpropane triglycidyl ether
  • the tear strength is 0.56 N
  • the yield point strength is 70.8 MPa
  • the elongation at break is 4.9%
  • the phase difference (N 400 ) at a wavelength of 400 nm is 5.39 nm
  • the phase difference (N 598 ) at a wavelength of 589 nm is 6.60 nm
  • the haze was 0.6 and the total light transmittance was 92%.
  • the resin composition of the present invention contains a combination of a fluorene compound and an epoxy compound, it can impart excellent properties derived from the fluorene compound to the resin without impairing mechanical properties. Further, the wavelength dispersion of the resin can be adjusted (for example, the wavelength dispersion of the resin can be reduced) by a combination of a fluorene compound and an epoxy compound.
  • the resin composition of the present invention is excellent in, for example, high refractive index, high heat resistance, high transparency, excellent moldability (such as high melt fluidity), although it depends on the type of resin constituting the resin composition. It has characteristics.
  • Such a resin composition is particularly useful for constructing (or forming) a molded product for optical use (optical molded product) because it is often excellent in optical properties.
  • Examples of the optical molded body formed (configured) with such a resin composition include optical films and optical lenses.
  • an optical film in addition to a phase film (or a retardation plate), a polarizing film (and a polarizing element and a polarizing plate protective film constituting the polarizing film), an alignment film (alignment film), a viewing angle expansion (compensation) film, a diffusion plate (Film), prism sheet, light guide plate, brightness enhancement film, near infrared absorption film, reflection film, antireflection (AR) film, reflection reduction (LR) film, antiglare (AG) film, transparent conductive (ITO) film, Anisotropic conductive film (ACF), electromagnetic wave shielding (EMI) film, electrode substrate film, color filter substrate film, barrier film, color filter layer, black matrix layer, adhesive layer or release layer between optical films, etc.
  • a phase film or a retardation plate
  • a polarizing film and a polarizing element and a polarizing plate protective film constituting the polarizing film
  • an alignment film alignment film
  • a viewing angle expansion (compensation) film a
  • the film of the present invention is useful as an optical film for use in an apparatus display.
  • the display member (or display) including the optical film of the present invention include FPD devices such as personal computer monitors, televisions, mobile phones, car navigation systems, and touch panels (for example, , LCD, PDP, etc.).

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Epoxy Resins (AREA)

Abstract

La présente invention concerne la préparation d'une composition de résine en rajoutant un composé ayant un squelette fluoré sans pour autant perdre ses propriétés mécaniques, ladite composition étant préparée en rajoutant, à une composition de résine autre qu'époxy, un composé époxy et un composé autre qu'époxy ayant un squelette 9,9-bisarylfluoré représenté par la formule (1). [Dans la formule : le cycle Z représente un cycle hydrocarbure aromatique ; R1 et R2 représentent un groupe substituant ; X représente le groupe -[(OR3)n-Y] (dans la formule : Y représente un groupe hydroxyle, un groupe mercapto, ou un groupe (méth)acryloyloxy ; R3 représente un groupe alkylène ; et n représente un entier au moins égal à 0) ou un groupe amino ; k représente un entier situé dans la plage allant de 0 à 4 ; m représente un entier au moins égal à 0 ; et p représente un entier au moins égal à 1.]
PCT/JP2014/060081 2013-04-10 2014-04-07 Composition de résine contenant un composé fluoré, corps moulé, agent d'ajustement de la dispersion des longueurs d'onde, et procédé d'ajustement de la dispersion des longueurs d'onde d'une résine WO2014168108A1 (fr)

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KR1020157027936A KR20150142682A (ko) 2013-04-10 2014-04-07 플루오렌 화합물을 포함하는 수지 조성물 및 성형체 및 파장 분산 조정제 및 수지의 파장 분산 조정 방법
JP2015511249A JPWO2014168108A1 (ja) 2013-04-10 2014-04-07 フルオレン化合物を含む樹脂組成物および成形体並びに波長分散調整剤および樹脂の波長分散調整方法
CN201480018415.XA CN105308122A (zh) 2013-04-10 2014-04-07 包含芴化合物的树脂组合物和成形体、以及波长色散调节剂和树脂的波长色散调节方法

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WO2016139826A1 (fr) * 2015-03-02 2016-09-09 大阪ガスケミカル株式会社 Agent améliorant la fluidité et composition de résine polyamide le contenant
WO2016147847A1 (fr) * 2015-03-13 2016-09-22 大阪ガスケミカル株式会社 Composition de résine et lentille optique
WO2017026250A1 (fr) * 2015-08-07 2017-02-16 大阪ガスケミカル株式会社 Composition de résine de polyamide renforcée de fibres et corps moulé à partir de celle-ci
JPWO2015147116A1 (ja) * 2014-03-28 2017-04-13 富士フイルム株式会社 （メタ）アクリル系樹脂組成物、フィルム、偏光板保護フィルム、偏光板及び液晶表示装置
JP2017210514A (ja) * 2016-05-24 2017-11-30 旭化成株式会社 ポリアミド樹脂組成物
JPWO2021171756A1 (fr) * 2020-02-28 2021-09-02

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KR102457502B1 (ko) * 2018-12-27 2022-10-21 삼성에스디아이 주식회사 편광판 및 이를 포함하는 액정표시장치
JP7121207B2 (ja) * 2020-01-08 2022-08-17 大阪ガスケミカル株式会社 位相差フィルムおよびその用途
CN115702214B (zh) * 2020-06-26 2024-02-20 三菱瓦斯化学株式会社 树脂组合物
CN114349965A (zh) * 2021-12-27 2022-04-15 江南大学 一种含s元素的高折射率光学树脂的制备方法

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WO2016139826A1 (fr) * 2015-03-02 2016-09-09 大阪ガスケミカル株式会社 Agent améliorant la fluidité et composition de résine polyamide le contenant
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WO2017026250A1 (fr) * 2015-08-07 2017-02-16 大阪ガスケミカル株式会社 Composition de résine de polyamide renforcée de fibres et corps moulé à partir de celle-ci
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