WO2008065912A1 - Élément optique en matière plastique, lentille pour capture optique utilisant celui-ci et dispositif de capture optique - Google Patents

Élément optique en matière plastique, lentille pour capture optique utilisant celui-ci et dispositif de capture optique Download PDF

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Publication number
WO2008065912A1
WO2008065912A1 PCT/JP2007/072276 JP2007072276W WO2008065912A1 WO 2008065912 A1 WO2008065912 A1 WO 2008065912A1 JP 2007072276 W JP2007072276 W JP 2007072276W WO 2008065912 A1 WO2008065912 A1 WO 2008065912A1
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group
optical element
optical
copolymer
dodecene
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PCT/JP2007/072276
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English (en)
Japanese (ja)
Inventor
Yayoi Eguro
Norikazu Arai
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Konica Minolta Opto, Inc.
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Priority to JP2008546947A priority Critical patent/JP5353243B2/ja
Publication of WO2008065912A1 publication Critical patent/WO2008065912A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F232/00—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
    • C08F232/02—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having no condensed rings
    • C08F232/04—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having no condensed rings having one carbon-to-carbon double bond
    • 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
    • G02B1/041—Lenses
    • G02B1/043—Contact lenses
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers

Definitions

  • the present invention relates to a novel plastic optical element with improved durability, and an optical pickup lens and optical pickup device using the same.
  • the optical pickup device includes an optical element unit that irradiates a medium with light having a predetermined wavelength emitted from a light source, and receives the reflected light with a light receiving element.
  • the optical element unit transmits the light to a reflection layer of the medium.
  • the optical element of the optical pickup device is preferably made of plastic as a material in that it can be manufactured at low cost by means such as injection molding.
  • plastic a copolymer of cyclic olefin and ⁇ -olefin is known (for example, see Patent Document 1).
  • the optical pickup device has a shape of both media and a wavelength of light to be applied. It is necessary to make the configuration corresponding to the difference. In this case, it is preferable from the viewpoints of economy and pick-up characteristics that the optical element unit is common to both the!
  • next-generation optical discs such as Blu-Ray Discs
  • the optical element has such short wavelength light irradiation.
  • the optical element itself becomes clouded or susceptible to fluctuations in the refractive index.As a result, the product life is shortened due to deterioration of these optical characteristics, and the optical element needs to be replaced. There was a case.
  • HALS an agent
  • the stability of optical elements when irradiated with light having a wavelength of around 400 nm over a long period of time is dramatically improved.
  • the transmittance fluctuated in the initial stage when the use was started due to heat Due to this initial transmittance variability, there is a possibility of causing poor reading due to the transmittance variation at the initial stage of use, and an immediate improvement is required.
  • Patent Document 1 JP 2002-105131 A (Page 4)
  • An object of the present invention is to provide a plastic optical element and an optical pickup having high-precision optical characteristics, high durability over a long period of time, and excellent optical stability in a short period of time.
  • the object is to provide a lens and an optical pickup device.
  • a plastic optical element comprising a copolymer of a-olefin and a cyclic olefin represented by the following general formula (I) or ( ⁇ ): 24 hours at 75 ° C or higher and 95 ° C or lower 15
  • n is 0 or 1
  • m is 0 or a positive integer
  • k is 0 or 1
  • R 1 to R 18 and R a and R b are each independently Represents a hydrogen atom, a halogen atom or a hydrocarbon group.
  • R 21 to R 39 are each independently hydrogen.
  • An atom, a halogen atom, a hydrocarbon group or an alkoxy group is represented.
  • the heat treatment at 75 ° C or more and 95 ° C or less for 24 hours or more and 1500 hours or less is performed after the plastic optical element is formed until it is used as a practical product. 2.
  • a plastic optical element comprising a copolymer of ⁇ -olefin and cyclic olefin represented by the following general formula (I) or (II), and when heated at 85 ° C for 1000 hours: The transmittance variation amount power at 405nm S, 1. Plastics within 2% Optical element.
  • n is 0 or 1
  • m is 0 or a positive integer
  • k is 0 or 1
  • R 1 to R 18 and R a and R b are each independently Represents a hydrogen atom, a halogen atom or a hydrocarbon group.
  • An optical pickup lens comprising the plastic optical element as described in any one of 1 to 3 above.
  • a plastic optical element and an optical pick-up element that have high-precision optical characteristics, have high durability over a long period of time, and excellent optical stability in a short period of time.
  • Lens and optical pickup device can be provided.
  • the present invention will be described in more detail.
  • excellent optical properties can be obtained by using ⁇ -olefin and a cyclic polyolefin copolymer represented by the above general formula (I) or ( ⁇ ) as components of the plastic optical element.
  • Ability to impart characteristics S when an optical pickup lens molded from the above copolymer is incorporated in an optical pickup device and used as an optical information recording / reproducing device incorporating the optical pickup device, the transmittance is irreversible due to changes in the usage environment. It became clear that it fluctuated. However, it has been found that this transmittance fluctuation is stable when heat treatment is performed at 75 to 95 ° C. for 24 to; 1500 hours, after which the rate of change is large.
  • the present inventor provides the use environment temperature of the optical pickup lens and the change in transmittance according to the time of exposure to the use temperature in advance before use as an optical information recording / reproducing apparatus.
  • the present inventor was able to provide a plastic optical element, an optical pickup lens, and an optical pickup device having extremely stable transmittance characteristics.
  • the heating temperature and the heating time are determined depending on whether the ⁇ -olefin according to the present invention and the cyclic olefin represented by the general formula (I) or ( ⁇ ) are added to the copolymer, or an addition described later to the copolymer.
  • the heating temperature is several points in the range of 75-95 ° C as a preliminary experiment.
  • the optimum heating temperature and heating time can be determined by setting and plotting the change in transmittance with heating time (range of 24 hours or more and 1500 hours or less).
  • the heat treatment is preferably performed after the resin composition is formed and before being used as a practical product.
  • the practical product in the present invention means a final product on which the plastic optical element of the present invention is mounted.
  • a state in which an optical pickup apparatus incorporating the optical element of the present invention is mounted to form an optical information recording / reproducing apparatus is a practical product.
  • the optical element or the optical pickup device of the present invention can be used by a user after being mounted on an optical information recording / reproducing device or the like.
  • Heat treatment at a point before being put into a state means.
  • the heat treatment is performed at the time before being incorporated into the optical pickup device, that is, in the state of the optical element.
  • a functional film such as an antireflection film
  • the material constituting the plastic optical element of the present invention is a copolymer comprising ⁇ -olefin and cyclic olefin represented by the general formula (I) or ( ⁇ ).
  • ⁇ is 0 or 1
  • m is 0 or a positive integer
  • k is 0 or 1.
  • the ring represented by k is a 6-membered ring, and when k is 0, this ring is a 5-membered ring.
  • R a and R b are each independently a hydrogen atom, a halogen atom or a hydrocarbon group.
  • the halogen atom is a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
  • the hydrocarbon group is usually an alkyl group having 1 to 20 carbon atoms, a halogenated alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 15 carbon atoms, or an aromatic hydrocarbon.
  • alkyl group include methyl group, ethyl group, propyl group, isopropyl group, amyl group, hexyl group, octyl group, decyl group, dodecyl group and octadecyl group.
  • These alkyl groups may be substituted with a halogen atom.
  • Examples of the cycloalkyl group include a cyclohexyl group, and examples of the aromatic hydrocarbon group include a phenyl group and a naphthyl group.
  • R 15 and R 16 are R 17 and R 18
  • R 15 and R 17 are R 16 and R 18
  • R 15 and R 18 are Alternatively, R 16 and R 17 may be bonded to each other (in cooperation with each other) to form a monocyclic or polycyclic group, or the monocyclic or polycyclic formed in this way may be used.
  • the ring may have a double bond. Shape here Specific examples of monocyclic or polycyclic rings include the following.
  • the carbon atom numbered 1 or 2 is bonded to R 15 (R 16 ) or R 17 (R 18 ) in the general formula (I), respectively. Represents a carbon atom.
  • An alkylidene group may be formed with R 15 and R 16 or with R 17 and R 18 !
  • Such an alkylidene group is usually an alkylidene group having 2 to 20 carbon atoms, and specific examples of such an alkylidene group include an ethylidene group, a propylidene group, and an isopropylidene group.
  • R 21 to R 39 are each independently a hydrogen atom, a halogen atom, a hydrocarbon group or an alkoxy group.
  • the hydrocarbon group usually includes an alkyl group having from 20 to 20 carbon atoms, a cycloalkyl group having from 3 to 15 carbon atoms, and an aromatic hydrocarbon group. More specifically, examples of the alkyl group include a methino group, an ethyl group, a propyl group, an isopropyl group, an amino group, a hexyl group, an octyl group, a decyl group, a dodecyl group, and an octadecyl group. These alkyl groups are substituted with halogen atoms! /, May! /.
  • Examples of the cycloalkyl group include a cyclohexyl group, and examples of the aromatic hydrocarbon group include an aryl group, an aralkyl group, and the like. Specifically, a phenyl group, a tolyl group, a naphthyl group, A benzyl group, a phenylethyl group, etc. are mentioned.
  • Examples of the alkoxy group include a methoxy group, an ethoxy group, and a propoxy group.
  • the carbon atom to which R 29 and R 3 ° are bonded and the carbon atom to which R 33 is bonded or R 31 And may be bonded directly or via an alkylene group having 1 to 3 carbon atoms. That is, when the above two carbon atoms are bonded via an alkylene group, R 29 and R 33 and force or R 3 ° and R 31 cooperate with each other to form a methylene group (—CH— ), Ethylene group (CH 2 CH 3) or propylene group (CH 2 CH 2 CH 3)! /, Forming any alkylene group! /
  • R 35 and R 32 or R 35 and R 39 may be bonded to each other to form a monocyclic or polycyclic aromatic ring.
  • R 35 and R 32 or R 35 and R 39 may be bonded to each other to form a monocyclic or polycyclic aromatic ring.
  • the following aromatic rings formed by R 35 and R 32 are exemplified.
  • q is synonymous with q in the general formula (II).
  • cyclic olefin represented by the general formula (I) or ( ⁇ ) include a bicyclo 1-2 heptene derivative (bicyclo hept-2-ene derivative), tricyclo 3- Decene derivatives, tricyclo-3-undecene derivatives, tetracyclo-3-dodecene derivatives, pentacyclo-4 pentadecene derivatives, pentacyclopentadecadene derivatives, pentacyclo-3-pentadecene derivatives, pentacyclo-3-hexadecene derivatives, pentacyclo-4 monohexadecene derivatives Hexacyclo-4 monoheptadecene derivatives, heptacyclo-5-eicosene derivatives, heptacyclo-4 eicosene derivatives, heptacyclo-5-heneicosene derivatives, octacyclo-5-
  • the ⁇ -olefins constituting the copolymer include, for example, ethylene, propylene, 1-butene, 1 pentene, 1-hexene, 1-year-old kuten, 1-tecene, 1-decene, 1-tetradecene 1-hexadecene, 1-octadecene, 1 eicosene and other linear ⁇ -olefins; 4-methyl-1 pentene, 3-methyl-1 pentene, 3-methyl-1-butene and other branched ⁇ -olefins.
  • a-olefin having 2 to 20 carbon atoms is preferred.
  • Such linear or branched ⁇ -olefins may be substituted with a substituent, or may be used alone or in combination of two or more.
  • Examples of the substituent include various types and are not particularly limited. Representative examples include alkyl, aryleno, anilino, asinoleamino, sulfonamido, alkylthio, arylthio, alkenyl, cycloalkyl, cycloalkenyl, Alkynyl, heterocycle, alkoxy, aryloxy, heterocyclicoxy, siloxy, amino, alkylamino, imide, ureido, snorefamoylamino, alkoxycarbonylamino, aralkyloxycarbonylamino, arrecoxycarbonyl, amino Reyloxycarbonyl, heterocyclic thio, thioureido, hydroxyl and mercapto groups, as well as spiro compound residues, bridged hydrocarbon compound residues, snorefoninore, snorfinoinole, snorfoninore
  • the alkyl group may be linear or branched, preferably having 1 to 32 carbon atoms.
  • a phenyl group is preferable.
  • Examples of the acylamino group include an alkylcarbonylamino group, an arylcarbonylamino group; examples of the sulfonamido group include an alkylsulfonylamino group, an arylsulfonylamino group; an alkylthio group, an alkyl component in the arylthio group, and an aryl group. Examples of the component include the above-described alkyl group and aryl group.
  • the alkenyl group having 2 to 23 carbon atoms as the alkenyl group and those having 3 to 12 carbon atoms, particularly 5 to 7 carbon atoms as the cycloalkyl group may be linear or branched.
  • the ureido group is an alkylureido group, an arylureido group; a sulfamoylamino group is an alkylsulfamoylamino group, an arylsulfamoylamino group; a 5- to 7-membered heterocyclic group Specific examples include 2 furyl, 2 cenyl, 2 pyrimidinyl, 2 benzothiazolyl, etc .; 5-7-membered saturated heterocycles include tetrahydrobiranyl, tetrahydrothio As the heterocyclic oxy group, those having a 5- to 7-membered heterocyclic ring are preferable, for example, 3, 4, 5, 6 tetrahydroviranilu 2-oxy, 1 phenyltetrazole-5-oxy, etc .; A 5- to 7-membered heterocyclic group is preferred as the heterocyclic group, such as 2-pyridylthio, 2-benzothiazoly
  • Examples of the sulfonyl group include an alkylsulfonyl group, an arylsulfonyl group, a norogen-substituted alkylsulfonyl group, a halogen-substituted arylsulfonyl group, and the like;
  • examples of the sulfiel group include an alkylsulfiel group, an arylsulfifer group, and the like.
  • Sulfonyloxy group is alkylsulfonyloxy group, arylylsulfonyloxy group, etc .
  • sulfamoyl group is N, N dialkylsulfamoyl group, N, N diarylsulfamoyl group, N-alkyl —N arylsulfamoyl, etc .
  • phosphoryl groups include alkoxy phosphoryl groups, aryloxyphosphoryl groups, alkylphosphoryl groups, arylylphospholinole groups, etc .
  • strong rubamoyl groups include N, N dialkyl-powered rubamoyl groups, N, N Diary carbamoyl group, N anorequinole N ally Rucarbamoyl group, etc .
  • a halogen-substituted alkoxy group such as an ⁇ -halogen-substituted alkoxy group; a norogen-substituted aryloxy group as a tetrafluoroallyl
  • examples thereof include a ruoxy group, a pentafluoroallyloxy group and the like; a pyrrolyl group such as 1 pyrrolyl and the like; and a tetrazolyl group such as 1-tetrazolyl and the like.
  • substituents such as trifluoromethyl, heptafluoro-ipropyl, nonylfluoro-tbutyl, tetrafluoroaryl group, pentafluoroaryl group and the like are also preferably used. Furthermore, these substituents may be substituted with other substituents.
  • the content of the acyclic monomer in the copolymer of the present invention is 20% by mass or more from the viewpoint of moldability.
  • S is preferably 30% or more, more preferably 25% or more and 90% or less. More preferably, it is 85% or less.
  • the glass transition temperature (Tg) of the copolymer according to the present invention is preferably in the range of 80 to 250 ° C, more preferably 90 to 220 ° C, and most preferably 100 to 200 ° C. .
  • the number average molecular weight (Mn) is a polystyrene conversion value measured by gel permeation chromatography (GPC), preferably ⁇ is 10,000 – 1, 000, 000, more preferably ⁇ is 20,000. It is in the range of —500,000, most preferably 50,000—300,000.
  • the molecular weight distribution is preferably 2.0 or less when expressed by the ratio (Mw / Mn) between the above Mn and the polystyrene-equivalent mass average molecular weight (Mw) similarly measured by GPC.
  • Mw / Mn is more preferably 1.8 or less, and particularly preferably 1.6 or less.
  • the temperature at the time of polymerization is selected from the range of 0 to 200 ° C, preferably 50 to 150 ° C, and the pressure is selected from the range of atmospheric pressure to 100 atm. Moreover, the molecular weight of the produced polymer can be easily adjusted by allowing hydrogen to be present in the polymer zone.
  • the olefin resin according to the present invention may be a polymer synthesized from a one-component cyclic monomer, but is preferably synthesized using two or more cyclic monomers or a cyclic monomer and an acyclic monomer.
  • the copolymer is selected. This copolymer may be produced using monomers having 100 or more components, but the mixing of monomers is preferably 10 or less in terms of production efficiency polymerization stability. More preferred is 5 components or less.
  • the obtained copolymer may be either a crystalline polymer or an amorphous polymer, but is preferably an amorphous polymer. Child is good.
  • the hydrogenation rate is increased and the hydrogenation is carried out, among those capable of using a known method.
  • a catalyst containing at least one metal selected from nickel, cobalt, iron, titanium, rhodium, noradium, platinum, ruthenium and rhenium is used in an organic solvent. It is preferable to carry out the hydrogenation reaction.
  • the hydrogenation catalyst either a heterogeneous catalyst or a homogeneous catalyst can be used.
  • the heterogeneous catalyst can be used as a metal or a metal compound or supported on a suitable carrier.
  • the support include activated carbon, silica, alumina, calcium carbide, titanium urea, magnesia, zircoure, diatomaceous earth, silicon carbide, and the like.
  • the supported amount of the catalyst is the metal content with respect to the total mass of the catalyst, usually 0. 0;! To 80% by mass, preferably 0.05 to 60% by mass.
  • Homogeneous catalysts are catalysts that combine nickel, cobalt, titanium, or iron compounds with organometallic compounds (eg, organoaluminum compounds, organolithium compounds), or rhodium, radium, platinum, ruthenium, rhenium, etc.
  • An organometallic complex catalyst can be used. These hydrogenation catalysts can be used alone or in combination of two or more, and the amount used is usually 0.0;! To 100 parts by mass per 100 parts by mass of the polymer. , Preferably 0.05 to 50 parts by mass, more preferably 0.;! To 30 parts by mass.
  • the hydrogenation reaction temperature is usually from 0 to 300 ° C, preferably from room temperature to 250 ° C, particularly preferably from 50 to 200 ° C.
  • the hydrogen pressure is usually 0.1 MPa to 30 MPa, preferably 1 MPa to 20 MPa, more preferably 2 MPa to 15 MPa.
  • the hydrogenation rate of the obtained hydrogenated product is usually 90% or more, preferably 95% or more of the carbon-carbon unsaturated bond of the main chain, as measured by 1H-NMR. Preferably it is 97% or more. If the hydrogenation rate is low, the optical properties such as transmittance, low birefringence, and thermal stability of the resulting polymer are lowered.
  • the solvent used in the hydrogenation reaction of the copolymer according to the present invention may be any one that dissolves the copolymer according to the present invention and the solvent itself is not hydrogenated! / Things
  • ethers such as tetrahydrofuran, jetyl ether, dibutyl ether, and dimethy réellen
  • aromatic hydrocarbons such as benzene, toluene, xylene, and ethylbenzene
  • aliphatic hydrocarbons such as pentane, hexane, and heptane
  • cyclopenta Aliphatic hydrocarbons such as cyclohexane, cyclohexane, methinorecyclohexane, dimethylenocyclohexane, decalin
  • halogenated hydrocarbons such as methylene dichloride, dichloroethane, dichloroethylene, tetrataroleethane, chlorobenzene, and trichlor
  • the copolymer hydrogenated product according to the present invention can be produced by isolating the copolymer hydrogenated product from the polymer solution and then dissolving it again in the solvent.
  • a method of performing a hydrogenation reaction by adding a hydrogenation catalyst composed of the above organometallic complex and an organoaluminum compound can also be employed.
  • acetic acid After the contact treatment of the solution or polymer slurry with a basic compound such as trimethylenediamine, aniline, pyridine, ethanediamide, sodium hydroxide in an atmosphere of nitrogen or hydrogen gas, or simultaneously with the contact treatment, acetic acid, Examples include a method in which an acidic compound such as citrate, benzoic acid and hydrochloric acid is subjected to contact treatment and then washed away.
  • a basic compound such as trimethylenediamine, aniline, pyridine, ethanediamide, sodium hydroxide in an atmosphere of nitrogen or hydrogen gas
  • acetic acid examples include a method in which an acidic compound such as citrate, benzoic acid and hydrochloric acid is subjected to contact treatment and then washed away.
  • the method for recovering the polymer hydride from the copolymer hydrogenated solution according to the present invention is not particularly limited, and a known method can be used.
  • the reaction solution is discharged into a poor solvent under stirring, and the polymer hydride is solidified and recovered by filtration, centrifugation, decantation, or the like, or polymer hydrogen is injected by blowing steam into the reaction solution.
  • Examples thereof include a steam stripping method for precipitating a chemical compound and a method for directly removing a solvent from a reaction solution by heating.
  • the hydrogenation rate can be easily achieved to be 90% or more, and can be 95% or more, particularly 99% or more.
  • the copolymer hydrogenated product becomes an excellent polymer or copolymer hydrogenated product that is not easily oxidized.
  • the hindered amine light-resistant stabilizer (hereinafter referred to as HALS) applicable to the plastic optical element of the present invention is not particularly limited, but the polystyrene equivalent Mn measured by GPC using tetrahydrofuran as a solvent is 1,000 to 10,000. Those that are 2000 are preferred, those that are 2000-5000 ⁇ , especially those that are 2800-3800. If Mn is too small, when HALS is blended by heat-melting and kneading into a block copolymer, a predetermined amount cannot be blended due to volatilization, and foaming will cause a leaky leak during heat-melt molding such as injection molding. The processing stability decreases.
  • HALS hindered amine light-resistant stabilizer
  • HALS HALS
  • the blending amount of the resin according to the present invention is preferably 0.0;! To 20 parts by mass, more preferably 0.02 to 15 parts by mass with respect to 100 parts by mass of the copolymer according to the present invention. Parts, particularly preferably 0.05 to 10 parts by mass. If the amount added is too small, the effect of improving light resistance cannot be obtained sufficiently, and coloring occurs when used outdoors for a long time. On the other hand, if the HALS content is too large, part of it will be generated as a gas, or the dispersibility in the resin will be reduced, and the transparency of the lens will be reduced.
  • HALS in addition to the above-mentioned HALS, other light stabilizers may be used in combination as long as the object effects of the present invention are not impaired.
  • benzophenone-based light stabilizers, benzotriazole-based light resistance A stabilizer or the like can be appropriately selected and used.
  • additives may be added as needed during the preparation of the resin composition according to the present invention and in the molding process of the resin composition! Can be added.
  • Additives are not particularly limited, but are stabilizers such as antioxidants, heat stabilizers, weathering stabilizers, UV absorbers, near infrared absorbers; resin modifiers such as lubricants and plasticizers; dyes and pigments Coloring agents such as antistatic agents, flame retardants, fillers and the like.
  • stabilizers such as antioxidants, heat stabilizers, weathering stabilizers, UV absorbers, near infrared absorbers
  • resin modifiers such as lubricants and plasticizers
  • dyes and pigments Coloring agents such as antistatic agents, flame retardants, fillers and the like.
  • Antioxidants include phenolic antioxidants, phosphorus antioxidants, and phenolic antioxidants. Examples thereof include phenolic antioxidants, and particularly alkyl-substituted phenolic antioxidants. By blending these antioxidants, it is possible to prevent coloration and strength reduction of the lens due to oxidative deterioration during molding without reducing transparency, heat resistance and the like. These antioxidants can be used alone or in combination of two or more, and the blending amount thereof is appropriately selected within a range not impairing the object of the present invention. Preferably, it is 0.00;! To 5 parts by mass, more preferably 0.0;! To 1 part by mass with respect to parts by mass.
  • phenolic antioxidant conventionally known ones can be used.
  • 2 t butynole 6- (3-t butyl-2 hydroxy-5 methylbenzyl) -4 methylphenyl acrylate
  • 2, 4 1-tamyl 6- (1- (3,5 di-tert-amyl 2-hydroxyphenyl) ethyl) phenyl acrylate and the like are described in JP-A 63-179953 and JP-A 1-168643.
  • the phosphorus antioxidant is not particularly limited as long as it is a substance usually used in the general resin industry.
  • triphenyl phosphite diphenyl isodecyl phosphite, phenyl diisodecyl phosphite, tris.
  • tris (noyulphenyl) phosphite tris (dinoylphenyl) phosphite, tris (2,4 di-tert-butylphenyl) phosphite and the like, which are preferred as monophosphite compounds, are particularly preferable.
  • iow antioxidants include dilauryl 3,3-thiodipropionate, dimyristinole 3,3'-thiodipropionate, distearyl 3,3-thiodipropionate, lauryl stearyl 3, 3-thiodipropionate, pentaerythritol tetrakisto (/ 3 lauryl thiopropionate), 3, 9 bis (2 dodecylthioethyl) 2, 4, 8, 10-tetraoxaspiro [5, 5] Undeccan.
  • the resin composition according to the present invention by blending the resin composition according to the present invention with a compound having the lowest glass transition temperature of 30 ° C or lower, various properties such as transparency, heat resistance, and mechanical strength are lowered. It can prevent white turbidity in high temperature and high humidity environment for a long time.
  • a resin composition comprising the resin composition according to the present invention and at least one compounding agent selected from the group consisting of (1) a soft polymer and (2) an alcoholic compound.
  • a compounding agent selected from the group consisting of (1) a soft polymer and (2) an alcoholic compound.
  • the soft polymer and (2) the alcoholic compound are excellent in the effect of preventing white turbidity in a high temperature and high humidity environment and the transparency of the resulting resin composition.
  • the soft polymer used in the present invention is usually a polymer having a Tg of 30 ° C. or lower. When a plurality of Tg are present, it is preferable that at least the lowest Tg is 30 ° C. or lower.
  • soft polymers include, for example, liquid polyethylene, polypropylene, poly-1-butene, ethylene'a-olefin copolymer, propylene' ⁇ -olefin copolymer, ethylene'propylene'gen.
  • EPDM olefin-based soft polymers
  • olefin-based soft polymers such as ethylene 'propylene' styrene copolymer, polyisobutylene, isobutylene 'isopropylene
  • Polyethylene polyisoprene, butadiene 'styrene random copolymer, isoprene' styrene random copolymer, acrylonitrile 'butadiene copolymer, acrylonitrile.
  • butadiene' styrene Copolymer butadiene styrene block copolymer, styrene 'butadiene.styrene' block copolymer, isoprene 'styrene' block copolymer, styrene 'isoprene styrene block copolymer, etc.
  • Polymers such as polymers, dimethylpolysiloxane, diphenylpolysiloxane, dihydroxypolysiloxane, etc., containing soft polymers, polybutyl acrylate, polybutyl methacrylate, polyhydroxyethyl methacrylate, polyacrylamide ⁇ , / 3-unsaturated soft polymers such as polyacrylonitrile, butyl acrylate, styrene copolymer, polybulal alcohol, poly (butyl acetate), polystearate, butyl acetate Soft polymers composed of unsaturated alcohols and amines or their derivatives or acetals, epoxy soft polymers such as ethylene oxide, polypropylene oxide, epichlorohydrin rubber, vinylidene fluoride rubber, tetrafluoride Fluorine-based soft polymers such as ethylene propylene rubber, other soft polymers such as natural rubber, polypeptides, proteins, polyester-based thermoplastic elastomers, chlorinated
  • a gen-based soft polymer is preferred.
  • a hydride obtained by hydrogenating a carbon-carbon unsaturated bond of the soft polymer has rubber elasticity, mechanical strength, flexibility, and dispersibility. Excellent in terms.
  • the alcoholic compound is a compound having at least one non-phenolic hydroxyl group in the molecule, and preferably has at least one hydroxyl group and at least one ether bond or ester bond.
  • Specific examples of such compounds include, for example, dihydric or higher polyhydric alcohols, more preferably trihydric or higher polyhydric alcohols, and even more preferably one of the hydroxyl groups of a polyhydric alcohol having 3 to 8 hydroxyl groups is an ether. Examples thereof include alcoholic ether compounds and alcoholic ester compounds that have been converted to esterification.
  • dihydric or higher polyhydric alcohol examples include, for example, polyethylene glycol, glycerol, trimethylololepronone, pentaerythritolol, diglyceronole, triglyceronole, dipentaerythritole, 1, 6, 7 trihydroxy.
  • polyhydric alcohols having a valence of 3 or more Particularly preferred are polyhydric alcohols having 3 to 8 hydroxyl groups.
  • glycerol, diglycerol, triglycerol or the like capable of synthesizing an alcoholic ester compound containing ⁇ , / 3-diol is preferable.
  • Examples of such alcoholic compounds include glycerin monostearate, glycerin monolaurate, glycerin monobehenate, diglycerin monostearate, glycerin distearate, glycerin dilaurate, pentaerythritol monostearate, Polyhydric alcoholic esterified products such as pentaerythritolol monolaurate, pentaerythritolol monobelate, pentaerythritololinorestearate, pentaerythritol dilaurate, pentaerythritol tristearate, dipentaerythritol distearate; 3- (octyloxy) 1,2-propanediol, 3- (decyloxy) 1,2-propanediol, 3 (lauryloxy) 1,2 propanediol, 3- (4-nourphenyl) 1) Reaction of glycidol
  • organic filler ordinary organic polymer particles or crosslinked organic polymer particles can be used.
  • polyolefins such as polyethylene and polypropylene
  • halogen-containing butyl polymers such as polyvinylolene chloride and polyvinylidene chloride.
  • Polymers derived from ⁇ , ⁇ unsaturated acids such as polyarylate and polymetatalylate; polymers derived from unsaturated alcohols such as polybulualcohol and polyacetate; polyethylene oxide or bisglycidyl ether Polymers derived from: Aromatic condensation polymers such as polyphenylene oxide, polycarbonate, polysulfone, etc .; Polyurethanes; Polyamides; Polyesters; Aldehyde ⁇ Phenol resins; Particles or crosslinks such as natural polymer compounds The ability to raise particles S.
  • Examples of inorganic fillers include Group 1 element compounds such as lithium fluoride and borax (sodium borate hydrate); Group 2 elements such as magnesium carbonate, magnesium phosphate, calcium carbonate, strontium titanate, and barium carbonate.
  • Group 1 element compounds such as lithium fluoride and borax (sodium borate hydrate)
  • Group 2 elements such as magnesium carbonate, magnesium phosphate, calcium carbonate, strontium titanate, and barium carbonate.
  • Group 4 element compounds such as titanium dioxide (titania) and titanium monoxide
  • Group 6 element compounds of molybdenum dioxide and molybdenum trioxide Group 7 element compounds such as manganese chloride and manganese acetate
  • Cobalt chloride and cobalt acetate Group 8 element compounds
  • Group 1 element compounds such as cuprous iodide
  • Group 12 element compounds such as zinc oxide and zinc acetate
  • Aluminum oxide (alumina), aluminum fluoride, aluminosilicate (alumina silicate, Group 13 element compounds such as kaolin and kaolinite
  • silicon oxide silicon oxide (silica, silica gel), graphite, Bon, graphite, Group 14 element compound such as glass; kernal stones, kainite, mica (My force, Kinunmo) include particles of natural minerals, such as Bairosu ore.
  • the compounding amount of the compounds (1) to (3) is a force S determined by the combination of the compound compounded with the alicyclic hydrocarbon-based copolymer. Generally, if the compounding amount is excessive, The transition temperature and transparency are greatly reduced, making it unsuitable for use as an optical material. If the blending amount is too small, the molded product may become cloudy at high temperature and high humidity.
  • the blending amount is usually from 0.01 to 10 parts by weight, preferably from 0.02 to 5 parts by weight, particularly preferably from 0.05 to 100 parts by weight per 100 parts by weight of the alicyclic hydrocarbon copolymer. 2 parts by mass is blended. If the amount is too small, the effect of preventing white turbidity in a high temperature and high humidity environment cannot be obtained. When there are too many compounding quantities, the heat resistance of a molded article and transparency will fall.
  • the resin composition according to the present invention is usually added to the resin at the stage of a processing process in which it is preferable to perform a specific processing process before the molding process (molding process).
  • Plasticizers including stabilizers, antioxidants, and other additives may be added.
  • a kneading process or a process of obtaining a composition by dissolving the mixture in a solvent, removing the solvent, and drying, and the like are listed as preferred methods S, particularly preferable preparation
  • the method is a kneading process.
  • a kneading process a kneading apparatus used for blending ordinary resins can be used. For example, a roll, a non-mixer mixer, a twin-screw kneader, a kneader loader, or the like can be used.
  • a single mixer, a twin-screw kneader, a kneader ruder, etc. are mentioned.
  • an apparatus capable of kneading in a closed system is preferably used, and more preferably, the kneading process is performed by inert gasification such as nitrogen or argon.
  • a resin composition (a resin alone or a mixture of a resin and an additive) is prepared, and then the obtained resin composition is prepared. Including the step of forming.
  • the molded product of the resin composition according to the present invention is obtained by molding a molding material comprising the resin composition.
  • the molding method is not particularly limited, but melt molding is preferable in order to obtain a molded product excellent in characteristics such as low birefringence, mechanical strength, and dimensional accuracy.
  • Examples of the melt molding method include commercially available press molding, commercially available extrusion molding, and commercially available injection molding. Injection molding is preferred from the viewpoints of moldability and productivity.
  • the molding conditions are appropriately selected depending on the purpose of use or the molding method.
  • the temperature of the resin composition in injection molding in the case of a resin alone or a mixture of a resin and an additive
  • Appropriate fluidity is imparted to the resin during molding to prevent sink marks and distortion of the molded product.
  • the range of 150 ° C to 400 ° C is preferred, more preferably 200 ° C. It is the range of -350 degreeC, Most preferably, it is the range of 200 degreeC-330 degreeC.
  • the plastic optical element of the present invention is characterized by being manufactured by performing a heat treatment at 75 ° C or more and 95 ° C or less for 24 hours or more and 1500 hours or less in the molding process as described above.
  • the heat treatment is preferably performed after the plastic optical element is molded and before it is used as a practical product! /.
  • the molded product according to the present invention can be used in various forms such as a spherical shape, a rod shape, a plate shape, a columnar shape, a tubular shape, a tubular shape, a fibrous shape, a film or a sheet shape, and has a low birefringence. Because of its excellent properties, transparency, mechanical strength, heat resistance, and low water absorption, it is also suitable as the force S used as the optical resin lens of the present invention and other optical components.
  • the plastic optical element of the present invention has high-precision optical characteristics, has long-term high durability and durability, and has excellent optical stability in a short period of time. It can be applied to various optical components.
  • the application range of the plastic optical element of the present invention includes, for example, an imaging lens of a camera as an optical lens and an optical prism; a lens such as a microscope, an endoscope, and a telescope lens; Transmission lens: CD, CD-ROM, WORM (write-once optical disk), MO (rewritable optical disk; magneto-optical disk), MD (mini disk), DVD (single f ⁇ lens, sensor lens, etc.
  • Optical disc applications include CD, CD-ROM, WORM (recordable optical disc), MO (rewritable optical disc; magneto-optical disc), MD (mini disc), DVD (digital video disc), etc. It is done.
  • Other optical applications include light guide plates such as liquid crystal displays; optical films such as polarizing films, retardation films, and light diffusion films; light diffusion plates; optical cards; and liquid crystal display element substrates.
  • a test plate having a cylinder temperature of 240 degrees, a thickness of 3 mm, a width of 20 mm, and a length of 50 mm was produced by an in-line injection molding machine. This was designated as Sample 1.
  • the obtained sample 1 was subjected to heat treatment in the atmosphere of 10% relative humidity at the heating temperature and heating time (hr) shown in Table 1 to obtain 42 types of heat-treated samples, respectively.
  • the aberration of Sample 1 was measured using a Zygo DVD400Pro interferometer.
  • the aberration of each heat-treated sample was measured by the same method.
  • Table 1 shows the evaluation results for the sample 1 obtained before the heat treatment and the change in the aberration after the heat treatment as aberration fluctuations (rms).
  • the case where the aberration fluctuation in evaluation 1 was less than 0 ⁇ 025 rms was marked as “ ⁇ ”, the case greater than 0.025 rms and less than or equal to 0 ⁇ 03 Orms, ⁇ , and the case greater than 0.003 rms as X.
  • the resulting 42 heat-treated samples were further treated for 1000 hours in an atmosphere at 85 ° C and 10% relative humidity, and the transmittance at 405 nm before and after 1000 hours treatment was measured according to JIS-R. — Measured using a spectrophotometer U-4000 model manufactured by Hitachi, Ltd. according to 1635, and the transmittance fluctuation amount (%) was obtained from the following equation.
  • Transmittance variation I Transmittance after 1000 hours treatment (%) — Transmittance before 1000 hours treatment
  • the transmittance fluctuation amount in Evaluation 2 is ⁇ when it is within 1.0%, ⁇ when it is larger than 1.0% and 1.2% or less, and X when it is larger than 1 ⁇ 2%.
  • sample 1 was molded into an optical pickup lens, 85 ° at three points: 1) heat treatment before anti-reflection coating, 2) after anti-reflection coating, and 3) as an integrated unit in the optical pickup unit. Heat treatment was performed under conditions of C and 336 hours, and coat cracks and coat adhesion were judged visually. The criteria are as follows, and the results are shown in Table 2.

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  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Optical Head (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Optical Record Carriers And Manufacture Thereof (AREA)
  • Treatments Of Macromolecular Shaped Articles (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

L'invention concerne un élément optique en matière plastique ayant des caractéristiques optiques à haute précision. Cet élément optique en matière plastique présente une durabilité élevée sur une longue période de temps, tout en étant excellent en termes de stabilité optique à court terme. L'invention concerne également une lentille pour une capture optique et un dispositif de capture optique. L'élément optique en matière plastique est caractérisé par le fait qu'il est composé d'un copolymère d'une α-oléfine et d'une oléfine cyclique représentée par la formule générale (I) ou (II) ci-après, et produit en étant chauffé à 75-95 °C pendant 24-1.500 heures.
PCT/JP2007/072276 2006-11-28 2007-11-16 Élément optique en matière plastique, lentille pour capture optique utilisant celui-ci et dispositif de capture optique WO2008065912A1 (fr)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010020877A (ja) * 2008-06-13 2010-01-28 Konica Minolta Opto Inc 光ピックアップ装置用の対物レンズ、光ピックアップ装置用の対物レンズの製造方法及び光ピックアップ装置
JP2010243888A (ja) * 2009-04-08 2010-10-28 Konica Minolta Opto Inc 光学素子及びその製造方法
JP2010271372A (ja) * 2009-05-19 2010-12-02 Konica Minolta Opto Inc 光学素子の製造方法及び光ピックアップ装置用の光学素子

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001235677A (ja) * 2000-02-24 2001-08-31 Konica Corp 対物レンズ及びｄｖｄ／ｃｄ互換光ピックアップ装置

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ATE450574T1 (de) * 2004-07-09 2009-12-15 Mitsui Chemicals Inc Harzzusammensetzung und verwendung davon

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001235677A (ja) * 2000-02-24 2001-08-31 Konica Corp 対物レンズ及びｄｖｄ／ｃｄ互換光ピックアップ装置

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010020877A (ja) * 2008-06-13 2010-01-28 Konica Minolta Opto Inc 光ピックアップ装置用の対物レンズ、光ピックアップ装置用の対物レンズの製造方法及び光ピックアップ装置
JP2010243888A (ja) * 2009-04-08 2010-10-28 Konica Minolta Opto Inc 光学素子及びその製造方法
JP2010271372A (ja) * 2009-05-19 2010-12-02 Konica Minolta Opto Inc 光学素子の製造方法及び光ピックアップ装置用の光学素子

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