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WO1997030119A1 - Composition de resine optique non birefringente et element optique constitue de celle-ci - Google Patents

Composition de resine optique non birefringente et element optique constitue de celle-ci Download PDF

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Publication number
WO1997030119A1
WO1997030119A1 PCT/JP1997/000385 JP9700385W WO9730119A1 WO 1997030119 A1 WO1997030119 A1 WO 1997030119A1 JP 9700385 W JP9700385 W JP 9700385W WO 9730119 A1 WO9730119 A1 WO 9730119A1
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WIPO (PCT)
Prior art keywords
methacrylate
groups
group
birefringence
resin composition
Prior art date
Application number
PCT/JP1997/000385
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English (en)
Japanese (ja)
Inventor
Yasuhiro Koike
Akihiro Yoshida
Minoru Suzuki
Hiromasa Kawai
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Hitachi Chemical Co., Ltd.
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Publication date
Application filed by Hitachi Chemical Co., Ltd. filed Critical Hitachi Chemical Co., Ltd.
Priority to JP52918997A priority Critical patent/JP3917662B2/ja
Publication of WO1997030119A1 publication Critical patent/WO1997030119A1/fr

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    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/252—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
    • G11B7/254—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of protective topcoat layers
    • G11B7/2542—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of protective topcoat layers consisting essentially of organic resins
    • 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
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/252—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
    • G11B7/253—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates
    • G11B7/2533—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates comprising resins

Definitions

  • the present invention relates to a non-birefringent optical resin material suitably used as a material for various optical elements, that is, a birefringent material that does not substantially exhibit ffl-folding properties or exhibits birefringence to such an extent that it has no practical effect.
  • the present invention relates to a non-birefringent optical resin composition having a glass transition temperature of not less than 10 crc and an optical element using the same.
  • optical plastics have come to be used due to the demand for lightweight and miniaturization.
  • polystyrene, polyacrylonitrile, polymethyl methacrylate, polystyrene / methacrylic acid methacrylate copolymer and the like are generally known. Since polystyrene and polycarbonate have an aromatic ring in the molecule, birefringence is likely to occur due to orientational distortion, and as shown in Japanese Patent Application Laid-Open No. 61-14617, the molding metal The type had to be changed.
  • polymethyl methacrylic acid which has a small photoelastic coefficient and relatively low birefringence due to orientation distortion, has been used for optical elements such as lenses for viewfinders and big-bub lenses for CDs.
  • optical elements such as lenses for viewfinders and big-bub lenses for CDs.
  • higher precision is required.
  • laser-up lenses for write-once optical disks that use laser light laser-up lenses for magneto-optical disks, write-once optical disks, magneto-optical disks, lenses for liquid crystal projectors and Fresnel lenses for liquid crystal projectors
  • the birefringence is close to zero and the in-plane distribution is extremely small or zero. Is required.
  • a liquid crystal element is one in which the birefringence of the member to be used is most important.
  • liquid crystal devices control the transmission and non-transmission of light by rotating the plane of polarization of the polarized light by the liquid crystal layer between the polarizer and the analyzer, which are made of two-or-two-cold or two-parallel colloids.
  • the birefringence of each of the constituent members has become a major problem, and this has prevented widespread use of optical resins for liquid crystal elements.
  • high precision is required for optical elements used in the devices, and resistance to environmental changes is required to maintain the accuracy. In particular, heat resistance is required.
  • optical plastics are required to have a high glass transition temperature as well as non-birefringence.
  • the optical device having the liquid crystal element and the laser single-up lens described above and the various disk substrates described above are used not only indoors but also in high temperatures such as in automobiles.
  • a plastic substrate used as a substitute for a glass substrate, which is one of the members constituting a liquid crystal element is exposed to high heat of at least 100 ° C. or more when depositing a transparent electrode.
  • Fresnel lenses for liquid crystal projectors are exposed to high temperatures because they are located very close to the light source.
  • modified acrylics, modified polyesters and alicyclic polyolefins have been developed as optical plastics that satisfy the high heat resistance required for the above-mentioned optical elements.
  • these highly heat-resistant plastics do not have zero force to reduce birefringence to some extent depending on molding conditions, and have a large in-plane distribution, so they should be used for optical elements that require high precision. Is difficult.
  • (1) a monomer capable of obtaining a resin having a positive photoelastic coefficient and a monomer capable of obtaining a resin having a negative photoelastic coefficient are required as raw materials.
  • Co photoelastic coefficient of the polymer one 1 X 10-3cm ⁇ Xd yne or more, + 1 X10- 3 C m2 / dyne method of copolymerizing to become less for (JP 60-18523 6 JP), (2) A method of copolymerizing methyl methacrylate, alkyl methacrylate having an alkyl group having 3 to 8 carbon atoms, and styrene (Japanese Patent Application Laid-Open Nos.
  • the present inventors have proposed a method for preparing a polymer having orientation birefringence, such as methyl polymethacrylate having negative orientation birefringence, which tends to offset the negative orientation birefringence.
  • orientation birefringence such as methyl polymethacrylate having negative orientation birefringence
  • These traditional methods have had some success and are still inadequate.
  • birefringence due to orientation distortion remains near the gate, which is insufficient as a non-birefringent material.
  • the resulting material is considerably inferior in heat resistance and transparency compared to PMMA, despite the birefringence near the gate being canceled out by the orientation, so it can be used for optical elements.
  • the method (1) has a drawback that the heat resistance is remarkably reduced by the addition of the dopant. For example, when biphenyl is added as a dopant to offset the orientation birefringence of PMMA, it is necessary to add as much as 7.3% by weight of biphenyl to PMMA.
  • the transition temperature is much lower / J than that of PMMA.
  • modified acrylics and the like have a higher glass transition temperature than PMMA, but also have a large negative alignment birefringence, so that it is necessary to add a large amount of dopant, and the alignment birefringence can be offset.
  • the glass transition temperature drops significantly.
  • the amount of the dopant added is small, the dopant and the base resin tend not to be uniformly mixed with each other, which is one of the causes of lowering the transparency.
  • materials obtained by this method from the viewpoints of heat resistance, transparency, and the like cannot be used for optical elements.
  • the present inventor has found that by copolymerizing MMA and an N-substituted maleimide compound at a specific ratio, it is possible to cancel the orientation birefringence and obtain a material having a high glass transition temperature. .
  • the reactivity between MMA and the N-substituted maleimide compound is not so good, so that a large amount of residual monomer is generated, and the obtained material is caused by the N-substituted maleimide compound.
  • monomers of N-substituted maleimide compounds are less soluble in monomers such as MMA.
  • an object of the present invention is to provide a non-birefringent optical resin composition having both high non-birefringence and heat resistance and an optical element using the same.
  • the present inventor has conducted intensive studies to achieve the above object.
  • the optical resin composition has high ⁇ , non-birefringence and high glass transition. They have found that temperature and temperature can be applied simultaneously, and have completed the present invention.
  • the present invention also provides an optical element utilizing the characteristics of the non-birefringent optical resin composition.
  • the present invention includes a copolymer containing an N-substituted maleimide compound as an essential copolymer component, and a dopant exhibiting an orientation birefringence which tends to offset the negative orientation birefringence of the copolymer.
  • the present invention relates to a non-birefringent optical resin composition and an optical element using the same.
  • the above copolymer comprises a methacrylic acid ester or an acrylic acid ester having an alicyclic hydrocarbon group having 5 to 22 carbon atoms in an ester portion, methyl methacrylate, an N-substituted maleimide compound, A copolymer obtained by copolymerizing these with a copolymerizable monomer is preferred.
  • the above copolymer has 5 to 40% by weight of a methacrylate or an acrylate having an alicyclic hydrocarbon group having 5 to 22 carbon atoms in an ester portion, and 5 to 9% by weight of methyl methacrylate.
  • the above dopant is represented by any of the general formulas (1) to (8) described below. It is preferable that at least one compound selected from the group consisting of In addition, the above dopant is blended in an amount within the range of 0.1 to 10 parts by weight based on 100 parts by weight of the copolymer containing the N-substituted maleimide compound as an essential copolymer component. Power ⁇ preferred.
  • the resulting non-birefringent optical resin composition preferably has a glass transition temperature of 100 ° C. or higher.
  • the non-birefringent optical resin composition of the present invention contains a copolymer having an N-substituted maleimide compound as an essential copolymer component and a dopant having a predetermined orientation birefringence.
  • N-substituted maleimide used in the present invention ⁇ ! For example, N-methyl maleimide, N-etinole maleimide, N-blovinole maleimide, N-i-brobi Lumalei Mid, N-Butyl Male Mid, Ni—Butyl Male Mid, NT—Butinole Male Mid, N—Hexinole Male Mid (2—phenyl phenyl) Male, N— (4—chlorophenyl) Male, N— (4-bromophenyl) phenyl Male, N— (2-methylphenyl) Male, N— (2— N- (2- (2-Methoxyphenyl) maleide, N- (2,4,6-trimethylphenyl) maleide, N— (4-benzylphenyl) maleide, N— (2,4,6-tribromophenyl) maleimide, etc.
  • N-methylmaleimide and N-ethylmaleimidate are preferable in terms of non-birefringence and heat resistance.
  • N-Provir Maleimide, N-I-Provir Maleimide, N-Butylmaleimide, Ni-Butylmaleimide, Nt-Butylmaleimide, N-Cyclohexylmaleimide, etc. Can be
  • copolymer used in the present invention other monomers other than the N-substituted maleimide compound may be used as a copolymer component.
  • Other monomers include: (1) methacryloleate or acrylate having an alicyclic hydrocarbon group having 5 to 22 carbon atoms in the ester portion; (2) methyl methacrylate; and (3) copolymerization with those used as necessary. Possible monomers are mentioned.
  • Examples of the methacrylate or acrylate having an alicyclic hydrocarbon group having 5 to 22 carbon atoms in the ester portion include, for example, cyclobentyl acrylate, cyclohexyl acrylate, methylcyclohexyl acrylate, and triacrylate acrylate.
  • Deca-4-methyl, decyl methacrylate and the like are preferred. Further, particularly preferable in terms of heat resistance are norbornyl methacrylate, norbornylmethyl methacrylate, tricyclomethacrylate [5.2.2.1.2.6] deca-1-yl and methacrylolate. Licyclo [5.2.1. 02. 6] Deca-4 monomethyl ⁇
  • Methyl methacrylate is the best monomer in terms of transparency, hue, mechanical properties, economical efficiency, etc.
  • the birefringence can be offset by adding. This thing These are used as one component of the copolymer in the present invention.
  • the copolymer used in the present invention includes a monomer copolymerizable with the N-substituted maleimide and the monomers (1) and (2) described above. As long as the properties, heat resistance and low hygroscopicity are not impaired, it can be used as needed.
  • this monomer examples include methyl acrylate, ethyl acrylate, buguchivir acrylate, n-butyl acrylate, iso-butyl acrylate, t-butyl acrylate, benchyl acrylate, n-acrylate —Hexyl, 2-ethylhexyl acrylate, n-octyl acrylate, dodecyl acrylate, octadecyl acrylate, butoxyshethyl acrylate, phenyl acrylate, benzinole acrylate, naphthyl acrylate, glycidyl acrylate, acrylic Acrylic acid esters such as 2-hydroxyhexyl acid, ethyl methacrylate, butyl methacrylate, n-butyl methacrylate, i-butyl methacrylate, t-butyl methacrylate, ventil methacrylate, n-methacrylate Hex
  • a methacrylate or an acrylate which has an alicyclic hydrocarbon group having 5 to 22 carbon atoms in an ester portion 5 to 90% by weight of methyl methacrylate.
  • the N-substituted maleimide compound is preferably 5 to 40% by weight, and the monomer copolymerizable therewith is preferably copolymerized in an amount within the range of 0 to 10% by weight. That is, the amount of the methacrylate or acrylate having an alicyclic hydrocarbon group having 5 to 22 carbon atoms in the ester portion is preferably in the range of 5 to 40% by weight, and 10 to 40% by weight.
  • the range of 30% by weight is particularly preferable in terms of hygroscopicity. If the content of the alicyclic (meth) acrylate is less than 5% by weight, the birefringence tends to be large and the hygroscopicity tends to be high. If it exceeds 40% by weight, the mechanical 3 ⁇ 4 ⁇ Tends to decrease.
  • the amount of methyl methacrylate is preferably in the range of 5 to 90% by weight, more preferably in the range of 10 to 80% by weight, and more preferably in the range of 50 to 80% by weight. It is particularly preferred that it is within the range. If the amount of methyl methacrylate is less than 5% by weight, the birefringence is large and the mechanical properties are reduced.
  • the compounding amount of the N-substituted maleimide compound is preferably from 5 to 40% by weight, and more preferably from 10 to 30% by weight in view of birefringence.
  • the amount of the N-substituted maleimide compound is less than 5% by weight, the birefringence is large and the heat resistance is high.
  • the content exceeds 40% by weight, the reactivity tends to decrease, and the amount of residual monomer tends to increase.
  • the material tends to be colored, and the birefringence increases.
  • a synthetic method such as a suspension polymerization method cannot be used.
  • Examples of the method for producing the copolymer include existing methods such as bulk polymerization, suspension polymerization, emulsion polymerization, and solution polymerization.
  • bulk polymerization is preferable from the viewpoint of mixing impurities into the resin, and suspension polymerization is preferable from the viewpoint of product handling.
  • a polymerization initiator can be used.
  • polymerization initiator examples include benzoyl peroxide, lauroyl peroxide, di-t-butylperoxyhexahydroterephthalate, t-butylperoxy-12-ethylhexanoate, and 1,11 Organic peroxides such as 3,3-, 5-trimethylcyclohexane, azobisisobutyronitrile, azobis-4-methoxy-2,4-dimethylvaleronitrile, azobiscyclohexanone 1 Radical polymerization, such as azo compounds such as 1-carbonitrile and abdibenzoyl; water-soluble catalysts such as potassium persulfate and ammonium persulfate; and redox catalysts in combination with peroxide or persulfate reducing agents.
  • the polymerization initiator is preferably used in the range of 0.01 to 10% by weight based on the total amount of the monomers.
  • benzoin ethers such as isobutyl benzoin ether, isobrovir benzoin ether, benzoin ethyl ether, and benzoin methyl ether, which are photopolymerization initiators, benzophenone, Ketones such as thioxanthone and chlorine-substituted benzophenone can be used.
  • a molecular weight regulator a mercaptan-based compound, thioglycol, carbon tetrachloride, ⁇ -methylstyrene dimer, etc. may be used as required. Can be added. In the case of thermal polymerization, the polymerization temperature can be appropriately selected from o to 2 o crc, and is 50 to 120. C is preferred. When using suspended polymerization, the polymerization is carried out in an aqueous medium, and a suspension agent and, if necessary, a suspension aid are added.
  • suspending agents include water-soluble polymers such as polyvinyl alcohol, methyl cellulose, and polyacrylamide, and insoluble inorganic substances such as calcium phosphate and magnesium pyrophosphate.
  • the water-soluble polymer is the total amount of monomers. It is preferably used in an amount of 0.03 to 1% by weight, and the hardly soluble inorganic material is preferably used in an amount of 0.05 to 0.5% by weight based on the total amount of the monomers.
  • the suspending aid include anionic surfactants such as sodium dodecylbenzenesulfonate. When a sparingly soluble inorganic substance is used as the suspending agent, it is preferable to use the suspending aid. .
  • the suspension aid is preferably used in an amount of 0.001 to 0.02 parts by weight based on 100 parts by weight of the copolymer component (monomer).
  • the dopant used in the present invention which exhibits the orientation birefringence tending to offset the negative orientation birefringence of the copolymer having the NS-substituted maleimide compound as an essential copolymer component, is as follows. Examples include compounds represented by any of the general formulas (1) to (8).
  • Ri, R 2 , R 3 and R 4 represent hydrogen, halogen such as F, Cl, Br, etc. Hydroxyl group, carboxyl group, amino group, cyano group, nitro group, nitroso group, thiol group, saturated or unsaturated aliphatic hydrocarbon group having 1 to 12 carbon atoms, alkoxyl group having 1 to 12 carbon atoms, 1 carbon atom ⁇ 12 acyl groups, 1 ⁇ 12 carbon acyloxy groups, carbon number!
  • Up to 12 alkyloxycarbonyl groups a hydrocarbon group having 1 to 4 carbon atoms having a hydroxyl group, a hydrocarbon group having 1 to 4 carbon atoms having a lumino group, Represents a secondary or tertiary amino group having a hydrocarbon group having 1 to 4 carbon atoms, m represents an integer of 1 to 4, and n represents an integer of 0 to 2.
  • A1-A2 which is a compound represented by the general formula (1)
  • A1 and A2 are selected from groups having the following structures, and A1 and A2 may be the same.
  • A1-X3-A2 which is a compound represented by the general formula (4), X3 is selected from groups having the following structures, A1 and A2 are the same groups as in the general formula (1), and A1 and A2 are the same. There may be. 7
  • X4 is a compound having any of the following structures.
  • X5 which is a compound represented by the general formula (6)
  • X5 is a compound having any of the following structures.
  • X6 which is a compound represented by the general formula (7)
  • X6 is selected from groups having the following structures
  • A1 and A2 are the same groups as in the general formula (1)
  • A1 and A2 are the same. Is also good.
  • X7 is selected from groups having the following structures, A1 and A2 are the same groups as in the general formula (1), and A1 and A2 may be the same. . X7:
  • the dopant (Al-A2 or A1-XI-A2) represented by the general formula (1) or (2), biphenyl, 4-bromo-3-nitrobiphenyl, 4,4-dibromobiphenyl, 3, 3'-dimethoxybenzidine, 3,3'-diaminobenzidine, 4-benzoylbiphenyl, 2,2'-biphenylcarboxylic acid, ⁇ . ⁇ '-diphenylpentidine, 2,6-diphenylphenol, 2-aminobiphenyl , 4-aminobiphenyl, 3,3'-dimethylbiphenyl, 4,4'-dimethylbiphenyl, 3,3'-dimethoxybiphenyl, 4,4'-dimethoxybiphenyl, 4-acetylbiphenyl, 2,2 ' -Biphenol, 4.4'-Biphenol, 4-Biphenyl acid, 4-Cyanobiphenyl, 4-Formylbiphen
  • Vivirazines such as 2,3-bis (2-pyridyl) virazine, etc., viridyl virazines such as 2,2′-biquinoline, 3,3′-aminonaphthidine and 3,3′-dimethylnaphthidine Binaphthalenes, 2-amino-4- (4-chlorophenyl) thiabool, 4- (4-biphenylyl) -2-methylthiazo Phenylthiazoles such as toluene, triphenyl-1H-tetrazol-5-thiol, 5-chloro-1_phenyl-1H-tetrazol, 5- (4-nitrophenyl) -1H-tetrazole, 3- (2-pyridyl) -5,6-diphenyl-1,2,4-tetrazole and other phenyltetrazoles, 2,2'-biimidazole, 2,2'-bis (4,5-dimethyl Biimidazoles such as thil
  • Phenylbenzimidazoles such asucimidazoles, 2-phenylbenzimidazole and 1-methyl-2-phenylbenzimidazole; pyridylbenzimidazoles such as 2- (2-pyridyl) benzimidazole Phenylindoles such as 2-phenylindole and 3- (2_nitrovinyl) -1-phenylindole, phenylnaphthalenes such as triphenylnaphthalene, 2-phenyl-1,3, Phenyl triazines such as 5-triazine, 2,4-diphenyl-1,3,5-triazine, 2,4.6-triphenyl-1,3,5-triazine, 4,7-diphenyl-1, Examples include pentafluoroanthrolines such as 10-phenanthroline.
  • biphenyl, P-terphenyl, 4'-bentyl-4-cyanobiphenyl, and 4 '-(4-bentylphenyl) -4-cyanobiphenyl are preferred in terms of non-birefringence and heat resistance.
  • the dopant (A1-X2-A2) represented by the general formula (3) includes diphenylmethane, 1,1-diphenylethane, 1J-diphenylethylene, 2,2'-diphenylpropane, and 1,1-diphenyl- 2-propanol, 3,3-diphenyl-1-propanol, diphenylacetonitrile, 1, didiphenylacetone, benzhydrol, 2,2-diphenylethanol, 2,2-diphenylethylamine, diphenylfurben, 2.2 -Diphenyl brobionic acid, 3,3-diphenyl brobionic acid, 2.2-diphenyl poroditriol, 3,3-diphenyl broviramine, ⁇ , ⁇ -diphenyl-4-biridinmethanol, diphenyl- 2-pyridylmethane, diphenyl-4-pyridylmethane, di-2-pyridylketoxime, 4-benzylisothiazo
  • Al—X3—A2 Specific examples of Al—X3—A2
  • Examples of the dopant (Al—X3-A2) represented by the general formula (4) include diphenyl ether, benzyl ether, 1,3-phenoxybenzene, 1,4-phenoxybenzene, and diphenoxy.
  • diphenyl ether diphenyl methane, 1,4-diphenyl benzene, diphenyl sulfide, diphenyl sulfide, diphenyl sulfone and diphenyls are preferable in terms of non-birefringence and heat resistance. Lufoxide and the like.
  • the dopant (X4) represented by the general formula (5) includes phenanthrene, 1-acetylfurenanthrene, 3-acetylphenanthrene, 9-acetylphenanthrene, and 9-aminophenanthrene Tren, 9-bromophenanthrene, 9-cyanophenanthrene, 9,10-diaminophenanthrene, 9,10-dihydrophenanthrene, 4H-cycloben [dei] phenanthrene, 9,10-dihydro-2 -Fuenantren Bulitchi 1,3,6-diphenylphenanthrene, 2,9-diphenylphenanthrene, 9-hydroxyphenanthrene, phenanthrene-9-carboxyaldehyde, phenanthrenequinone, 1.2.3, 4- Phenanthrenes such as tetrahydrophenanthrene-toluone, fluorene, 2-amino-7-bromofluorene, 2-amino
  • dopant (X5) represented by the general formula (6), 5-amino-6-nitroquinoline, 4-aminoquinoline, 5-aminoquinoline, 3-aminoquinoline, 6-aminoquinoline, and 8-aminoquinoline 7,8-benzoquinoline, 9-bromoquinoline, 7-chloro-4-hydrazinoquinoline, 5-chloro-8-hydroxyquinoline, 4-chloroquinaldine,
  • 8-Hydroxyquinaldine 4-Hydroxyquinoline, 5-Hydroxyquinoline, 2-Hydroxyquinoline, 8-Hydroxyquinoline, 8-Hydroxyquinoline N-oxide, 3-Hydroxy-2 -Quinoline carboxylic acid, 4-hydroxyquine-7-trifluoromethyl-3-quinoline carboxylic acid, 6-methoxy-8-ditroquinoline, 6-methoxyquinaldine, 6-methoxyquinoline, 4-methoxy 2-quinoline carboxylic acid, 6-methylquinoline, 7-methylquinoline, 8_methylquinoline, 8-nitroquinoline, 5-nitroquinoline, 6-nitroquinoline, 4-nitroquinoline N-oxide, quinoline, 3 -Quinoline carbitolyl, 2-quinoline carbaldehyde, 3-quinoline carbaldehyde, 4-quinoline carbaldehyde, 2-quinoline carboxylic acid, 3-quinoline carboxylic acid, 4-quinoline Boric acid, 2,
  • Quinozalins such as 5-methylquinosaline and 3-methyl-2-quinozariol; cinnolines such as cinolin, cinolin-4-carboxylic acid; imidazopyridines such as quinazolines such as 4-hydroxyquinazoline, 2-mercaptothiazoline and quinazoline; 2-amino-benzimidazole, benzimidazole, 2-amino-5,6-dimethylbenzimidazole, 4-azabenzimidazole, benzimidazole, 5-benzimidazole-5-carboxylic acid, 2- Mercaptobenzoimidazole, 2-benzimidazole acetonitrile, 2- (chloromethyl) benzimidazole, 2- (4-fluorophenyl) -trimethylbenzimidazole, 2-mercapto-5-nitro Benzoimidazole, 2-methylbenzimidazole, 5-methylbenzimidazole, 2- (methylmerbutane) ben Imidazole, 2-methyl-5-nitro
  • 6-dimethylbenzothiazole 2-amino-6-ethoxybenzothiazole, 2-amino-4-methoxybenzothiazole, 2-amino + methylbenzothiazole, 2-amino-6-methylbenzothiazole Zol, 2-amino-6-nitrobenzothiazole, benzothiazole, 2-mercaptobenzothiazole, 2-chlorobenzotothiazole, 5-chlorobenzotothiazole, 5-chloro-2-mercaptobenzothiazole, 2,5-dimethylbenzothiazole, 6-ethoxy-2-benzothiazolesulfonamide, 6-ethoxy-2-mercaptobenzothiazole, 6-methoxy-2-methylbenzthiazole, 2-methylbenzil Benzothiazoles such as zothiazole, 2,1,3-benzothiadiazole, benzothiadiazoles such as 4-nitro-2,1,3-benzothiadiazole, phenothiazine, 2-chlorophen
  • acridine dibenzofuran, dibenzothiophene, xanthene, 1,7-phenanthroline phosphorus, 1,10-phenanthroline phosphorus, and non-birefringence and heat resistance. , 7-phenanthroline and the like.
  • the dopants (Al—X6-A2) represented by the general formula (7) include diphenylamine, diphenylamine-2,2-dicarboxylic acid, ⁇ , ⁇ ′-diphenylbenzidine, ⁇ , ⁇ ′- Diphenylethylenediamine, ⁇ , ⁇ -diphenylformamide, 1.3-diphenylguanidine, 1,2-diphenylhydrazine, ⁇ , ⁇ '-diphenyl-1,4-phenylenediamine , 1,2-diphenyl-2-vicrylhydrazine, 4,4-diphenylsemicarbazide, 1.3-diphenyl-2-thioperea, 1,3-diphenylurea, 1.3-bis (3-pyridylmethyl) -2-thioperea, 2,2'-dipyridylamine, 4- (4-nitrophenylazo) diphenylamine, 1,3-ditolyl-2-thioperea, 2-benzylamino
  • N-benzylidaniline N-benzylidene-4-cyanoaniline
  • N-benzylidenebenzylamine N-benzylidenebenzylamine
  • azobenzene N-phenylphthalimid
  • N-benzylphthalimid N-benzylphthalimid and the like.
  • the compounds (A1-X7-A2) represented by the general formula (8) include benzophenone, 1,3-diphenylacetone, 3,3'.4,4'-benzophenonetetracarboxylic acid Anhydride, 2-aminobenzophenone, 4-aminobenzophenone, 2-aminobenzophenone-2'-carboxylic acid, 2- (3-amino-4_cyclobenzoyl) benzoic acid, 2-amino -4-Methylbenzophenone, 2-amino-5-nitrobenzophenone, 2-amino-3-nitrobenzophenone, 2-methylbenzophenone, 3-methylbenzophenone, 4-methylbenzophenone Nzophenone, benzyl, 2-benzoylbenzoic acid, 3-benzoylbenzoic acid, 4-benzoylbenzoic acid, 1,2-dibenzoylbenzene, 4-bromobenzophenone, 2- (4-chlorobenzoyl) benzoic acid Acid, 2- (4-
  • benzoyl is preferable in terms of non-birefringence and heat resistance.
  • examples include phenone, 4-benzoylbiphenyl, benzyl benzoate, 4-cyanophenyl-4-benzyl benzoate, 4'-cyanophenyl-4-benthiol benzoate and the like.
  • the amount of the dopant is preferably in the range of 0.1 to 10 parts by weight based on 100 parts by weight of the copolymer component (monomer) depending on the type of dopant. From the viewpoint of heat resistance, 0.5 to 7 parts by weight is particularly preferable. If the amount is less than 0.1 part by weight, the effect of reducing birefringence is reduced, and if it exceeds 10 parts by weight, heat resistance tends to decrease. In addition, it tends not to mix uniformly with the base resin, which causes a loss of transparency.
  • a compounding method of the dopant according to the present invention a method of mixing a dopant before starting the polymerization reaction for synthesizing the copolymer or after starting and before finishing the polymerization reaction can be adopted.
  • the non-birefringent optical resin composition of the present invention preferably has a glass transition temperature of 100 or more.
  • Examples of the method for producing the composition include a method in which a dopant is added to a heated melt of the copolymer, and the dopant is dispersed in the copolymer through a process of kneading the dopant. It is preferable that the material sufficiently kneaded based on the present method be pelletized by an appropriate means. Further, as described above, instead of the method of adding and kneading a dopant that offsets the negative alignment birefringence in the heating and melting step, the copolymer is dissolved in an appropriate solvent, and the negative alignment birefringence is contained therein. Add a compound that offsets the properties and mix evenly.
  • a process of removing the solvent by an evaporation step or the like can be used.
  • a copolymer obtained by suspension polymerization, bulk polymerization, solution polymerization, or the like is added to a solvent in which the copolymer is soluble in 5 to 20%. After dissolving at a concentration by weight and further adding a dopant, a film of about 50 was prepared, and a double-refraction-free compound was obtained when the film was stretched twice (stretching temperature: 90 ° C). A method of searching for quantities is employed.
  • the non-birefringent optical resin composition of the present invention is used, from the viewpoints of deterioration prevention, thermal stability, moldability and workability, it is preferable to use a phenol-based, phosphite-based or thioether-based antioxidant.
  • Release agents such as fatty alcohols, fatty acid esters, phthalic acid esters, triglycerides, fluorosurfactants, metal salts of higher fatty acids, other lubricants, plasticizers, antistatic agents, ultraviolet absorbers, flame retardants And a heavy metal inactivating agent.
  • the non-birefringent optical resin composition according to the present invention is particularly suitable for a member for a liquid crystal element in the above-described various properties.
  • a member for a liquid crystal element for example, an LCD substrate interposed between a liquid crystal layer and a polarizing plate is an example.
  • the glass-based optical It is possible to improve the various performances of liquid crystal devices by taking advantage of the optical resin material in comparison with the material.
  • a polarizing plate for a liquid crystal element is formed by bonding a transparent resin sheet to both surfaces of a polarizer.
  • the use of the non-birefringent optical resin according to the present invention for this transparent resin sheet is also particularly suitable.
  • the use of the non-birefringent optical resin composition of the present invention as an adhesive used for bonding each element forming a liquid crystal element is also a preferable use method that can effectively utilize the high non-birefringence. is there. That is, in the conventional liquid crystal element, since there is no resin material for the adhesive having a high non-birefringence, each of the liquid crystal elements except for a case where such a high non-birefringence is not required, such as a monochrome evening, is used. Although the joining of the elements is made with an adhesive, the use of an adhesive using the non-birefringent optical resin according to the present invention instead of the adhesive makes it possible to improve durability and heat resistance. The performance of the liquid crystal element can be improved.
  • the application of the non-birefringent optical resin to the optical element uses a known molding method such as an injection molding method, a compression molding method, a micromolding method, a floating molding method, a mouth-links method, and a casting method. can do.
  • a known molding method such as an injection molding method, a compression molding method, a micromolding method, a floating molding method, a mouth-links method, and a casting method. can do.
  • the casting method after partially polymerizing, the mixture is injected into a mold, and the final polymerization is performed to obtain a molded product and at the same time, the non-reflective optical resin according to the present invention is manufactured. Is also good.
  • moisture-resistance, optical properties, chemical resistance, Abrasion resistance, anti-fog, etc. can be improved.
  • the optical element in the present invention include a general camera lens, a video camera lens, a laser big-up lens, a laser printer f-6 lens, a Fresnel lens, a liquid crystal projector single lens, and a spectacle lens.
  • Lens con Pact disks (CD, CD-ROM, etc.), mini disks (MD), DVD disk substrates, LCD substrates, polarizing film transparent resin sheets, retardation films, light diffusion films, adhesives for bonding liquid crystal elements, etc.
  • an optical resin composition having high non-birefringence and heat resistance can be obtained without being restricted by the conventional methods. Further, the present invention can provide an optical element utilizing the characteristics of the non-birefringent optical resin composition.
  • FIG. 1 is a schematic view of a test piece for measuring birefringence of a molded article used in an example of the present invention.
  • the water-soluble polymer (A) (polymethacrylate) used as a suspending agent in the following examples was synthesized by the following method.
  • Tricyclo methacrylate [5.2. 1. 02.6] 8-yl 360 g, methyl methacrylate 128 Og, N-cyclohexyl maleimide (Nippon Shokubai Imilex C) 360 g , 60 g of biphenyl, 8 g of lauroyl peroxide (Parinole L, manufactured by NOF Corporation), 2 g of t-butylvinyloxyisobrobyl carbonate (Patyl I, manufactured by NOF Corporation), and 4 g of n-octylmercaptan Then, 0.1 g of the above jelly-like water-soluble polymer (A) and 2500 g of deionized water were added as suspending agents to a 5 L autoclave equipped with a stirrer, and then phosphorus was added.
  • the combined buffer solution of sodium sodium oxyhydrogen and sodium dihydrogen phosphate was added and stirred, and the pH was adjusted to 7.2 to prepare a suspension medium.
  • the above monomer mixture was added thereto with stirring, and the mixture was polymerized under stirring at a rotation speed of 27 Orpra at 60 ° C for 3 hours under a nitrogen atmosphere, and then sealed at 120 ° C for 2 hours at 120 ° C to obtain resin particles.
  • the polymerization rate was 99% by gravimetric method
  • the resin particles are washed with water, dehydrated, and dried, and molded by Toshiba Machine Co., Ltd. using an injection molding machine IS-50 EP at a cylinder temperature of 260 ° (injection speed of 50 cm3 / sec, mold temperature of 90,
  • the holding pressure was increased (stress and strain was applied) to reduce the amount of cushion as much as possible.
  • the holding pressure was set to provide an appropriate cushion amount.
  • Tricyclocyclomethacrylate [5.2.1.02.6] deca-1-yl 300 £, methyl methacrylate 1400 g, N-cyclohexylmaleimide (Nippon Shokubai Co., Ltd .: trade name: Imirex C) 200g, Benzyl methacrylate 100g :, Biphenyl 40g, Lauroyl peroxide (Nippon Oil & Fats Co., Ltd .: Trade name: Paryl L) 8g, t-butyl benzoic acid sodium Manufactured by: Trade name: Perbutinol I) 2 g, 4 g of n-butyloctyl mercaptan were dissolved to prepare a monomer mixture, and the same procedure as in Examples 1 and 2 was carried out. Obtained.
  • the glass transition temperature (Tg) of the obtained resin particles was measured using a differential scanning calorimeter (DSC7 manufactured by PerkinElmer).
  • Table 1 show that the optical resin composition obtained by the present invention has excellent non-birefringence in orientation birefringence and birefringence of a molded article.
  • Evaluation results Monomer composition (parts by weight)- ⁇ ⁇ ⁇ ⁇ Orientation birefringence Kun Young amount birefringence () Tg ⁇ A TCDMA CHMI BZMaMS (weight 3 ⁇ 4) * E-5 (—) (ram) A point B point (° C)
  • Example 1 64 18 18 BP 3% Less than 0.1 0.3 2 I I2l
  • Example 2 64 18 18-BP 3% Less than 0.1 2.5 10 I2l
  • Example 3 64 18 18 P 4% Less than 0.1 0.1 Ill9
  • Example 4 64 18 18-DPM 4% 0.1 Not yet? g
  • Example 5 64 18 18 DPE 4.5% less than 0.1 0.3-1 0 118
  • Example 6 64 18 18 DPE 4.5% less than 0.1 2.3 1 0 118
  • Example 7 64 18 18 FL 1.8% Less than 0.1 0.40 0 126
  • Example 8 64 18 18 FL 1.8% Less than 0.1 2.5 0 -I 126
  • Example 9 64 18 18 AD 2.5% Less than 0.1 0 4 1 I 123
  • Example 10 64 18 18 AD 2.5% Less than 0.1 2 4 1 0 123
  • Example 12 64 18 18 ⁇ ⁇ BCA 3.2% Less than 0.1 2 5-1 I 121
  • Example 13 64
  • Example 22 64 18 18 PPI 4.5% Less than 0.1 2.4 0 0 117
  • Example 23 70 15 10 5 ⁇ BP 2% less than 0.1 0 • 3 1 1 115
  • Example 24 70 15 10 5 ⁇ BP 23 ⁇ 4 Less than 0.1 2.2 : 1 0 115
  • Example 25 70 15 10 5 One DPM 2.5% 0.1 Less than 0.3 ()-1 113
  • Example 26 70 15 10 5 One DPM 2.5% less than 0.1 2.5 1 1 0 113
  • Example 27 70 15 10 5 One DPE 2.8% Less than 0.1 0.4] ⁇ 1 110
  • Example 28 70 15 10 5 DPE 2.8% Less than 0.1 2.3 () 0 110
  • Example 29 70 15 10 5 ⁇ FL 1.2% Less than 0.1 0.3 ()-1 117
  • Example 30 70 15 10 5 ⁇ FL 1.2 % Less than 0.1 2.5 1 0 117
  • Example 31 70 15 10 5 ⁇ A 1.8% Less than 0.1 0.4 0.14 115
  • Example 32
  • Example 33 70 15 10 5 1 BCA 2.5% Less than 0.1 0 .. 1 1 113
  • Example 34 70 15 10 5 ⁇ BCA 2.5% Less than 0.1 2., 5 C 1 -1 113
  • Example 35 70 15 10 5 One BB 2.6% less than 0.1 0.3 2: 1 112
  • Example 36 70 15 10 5 ⁇ BB 2.6% less than 0.1 2.5 .1 -1 112
  • Example 37 70 15 10 5 ⁇ DMBP 2% less than 0.1 0.3 1 0 115
  • Example 39 70 15 10 5 DMBP 2% Less than 0.1 2.3 C 1 1 115
  • Example 40 70 15 10 5 One DMT 1.8% Less than 0.1 0,, 3 0 1 1 115
  • Example 41 70 15 10 5 One DMT 1.8% Less than 0.1 2.4 4-1 115
  • Example 42 70 15 10 5 One CPPB 1.9% 0.1 Less than 0,, 3 1 0 115
  • Example 43 70 15 10 5 ⁇ CPPB 1.9% less than 0.1 2.3 C
  • Example 59 63 5 30-2 BB 2% 0-1 Not yet? el 2.2 1 1 135
  • Example 60 63 5 30-2 BB 2% Less than 0.1 0.3 0 1 135
  • Example 61 63 5 30-2 DMBP 2.2% 0 ⁇ lTf 2.5 1 0 135
  • Example 62 63 5 30- 2 DMBP2.2% 0
  • Comparative Example 4 100 11-DPM 9%
  • the non-birefringent optical resin composition of the present invention and the optical element using the same are suitably used for various optical device lenses and liquid crystal element members.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Optical Record Carriers And Manufacture Thereof (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

Composition de résine optique non biréfringente présentant des caractéristiques excellentes de non biréfringence, de résistance à la chaleur et comprenant un polymère composé d'un maléimide N-substitué en tant que comonomère essentiel et d'un dopant possédant une biréfringence d'orientation tendant à équilibrer la biréfringence d'orientation négative du polymère. Un élément optique fabriqué au moyen de ladite composition est aussi décrit.
PCT/JP1997/000385 1996-02-14 1997-02-14 Composition de resine optique non birefringente et element optique constitue de celle-ci WO1997030119A1 (fr)

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JP52918997A JP3917662B2 (ja) 1996-02-14 1997-02-14 非複屈折性光学用樹脂組成物及びこれを用いた光学用素子

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1403297A1 (fr) * 2002-09-30 2004-03-31 Tosoh Corporation Matériau optique de résine transparente et thermorésistante et film
JP2005068374A (ja) * 2003-08-27 2005-03-17 Yasuhiro Koike 非複屈折性光学樹脂材料、同材料の製造方法並びに同材料を用いた光学素子
JP2011209627A (ja) * 2010-03-30 2011-10-20 Nippon Shokubai Co Ltd 位相差フィルムとこれを備える画像表示装置
JP2013231128A (ja) * 2012-04-27 2013-11-14 Kuraray Co Ltd （メタ）アクリル樹脂組成物
US9246108B2 (en) 2012-12-28 2016-01-26 Dow Global Technologies Llc Quinoline-benzoxazole derived compounds for electronic films and devices
JP2017145281A (ja) * 2016-02-15 2017-08-24 東ソー株式会社 樹脂組成物
JP2018104721A (ja) * 2012-05-15 2018-07-05 旭化成株式会社 メタクリル系樹脂の製造方法、メタクリル系樹脂、及び成形体
US11427558B1 (en) 2019-07-11 2022-08-30 ESCAPE Bio, Inc. Indazoles and azaindazoles as LRRK2 inhibitors
US12294057B2 (en) 2021-08-26 2025-05-06 Lg Energy Solution, Ltd. Non-aqueous electrolyte solution and lithium secondary battery including the same

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JPS60185236A (ja) * 1984-03-03 1985-09-20 Matsushita Electric Works Ltd 光学式デイスク
JPS63248812A (ja) * 1987-04-03 1988-10-17 Kyowa Gas Chem Ind Co Ltd 光学素子用共重合体の製造法
JPH0476013A (ja) * 1990-07-17 1992-03-10 Hitachi Chem Co Ltd 光学用素子
JPH06116331A (ja) * 1992-10-07 1994-04-26 Toray Ind Inc 透明耐熱樹脂材料および光学用成形体

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JPS60185236A (ja) * 1984-03-03 1985-09-20 Matsushita Electric Works Ltd 光学式デイスク
JPS63248812A (ja) * 1987-04-03 1988-10-17 Kyowa Gas Chem Ind Co Ltd 光学素子用共重合体の製造法
JPH0476013A (ja) * 1990-07-17 1992-03-10 Hitachi Chem Co Ltd 光学用素子
JPH06116331A (ja) * 1992-10-07 1994-04-26 Toray Ind Inc 透明耐熱樹脂材料および光学用成形体

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1403297A1 (fr) * 2002-09-30 2004-03-31 Tosoh Corporation Matériau optique de résine transparente et thermorésistante et film
US7001967B2 (en) 2002-09-30 2006-02-21 Tosoh Corporation Transparent heat-resistant resin optical material and film
JP2005068374A (ja) * 2003-08-27 2005-03-17 Yasuhiro Koike 非複屈折性光学樹脂材料、同材料の製造方法並びに同材料を用いた光学素子
JP4536344B2 (ja) * 2003-08-27 2010-09-01 康博 小池 非複屈折性光学樹脂材料、同材料の製造方法並びに同材料を用いた光学素子
JP2011209627A (ja) * 2010-03-30 2011-10-20 Nippon Shokubai Co Ltd 位相差フィルムとこれを備える画像表示装置
JP2013231128A (ja) * 2012-04-27 2013-11-14 Kuraray Co Ltd （メタ）アクリル樹脂組成物
JP2018104721A (ja) * 2012-05-15 2018-07-05 旭化成株式会社 メタクリル系樹脂の製造方法、メタクリル系樹脂、及び成形体
US9246108B2 (en) 2012-12-28 2016-01-26 Dow Global Technologies Llc Quinoline-benzoxazole derived compounds for electronic films and devices
JP2017145281A (ja) * 2016-02-15 2017-08-24 東ソー株式会社 樹脂組成物
US11427558B1 (en) 2019-07-11 2022-08-30 ESCAPE Bio, Inc. Indazoles and azaindazoles as LRRK2 inhibitors
US12294057B2 (en) 2021-08-26 2025-05-06 Lg Energy Solution, Ltd. Non-aqueous electrolyte solution and lithium secondary battery including the same

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