WO2008015999A1 - Matériau composite et élément optique - Google Patents

Matériau composite et élément optique Download PDF

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Publication number
WO2008015999A1
WO2008015999A1 PCT/JP2007/064869 JP2007064869W WO2008015999A1 WO 2008015999 A1 WO2008015999 A1 WO 2008015999A1 JP 2007064869 W JP2007064869 W JP 2007064869W WO 2008015999 A1 WO2008015999 A1 WO 2008015999A1
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WO
WIPO (PCT)
Prior art keywords
composite material
resin
compound
adamantyl group
oxide
Prior art date
Application number
PCT/JP2007/064869
Other languages
English (en)
Japanese (ja)
Inventor
Hiroaki Ando
Shinichi Kurakata
Original Assignee
Konica Minolta Opto, Inc.
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 Konica Minolta Opto, Inc. filed Critical Konica Minolta Opto, Inc.
Priority to JP2008527739A priority Critical patent/JPWO2008015999A1/ja
Publication of WO2008015999A1 publication Critical patent/WO2008015999A1/fr

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Classifications

    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • 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
    • G11B7/12—Heads, e.g. forming of the optical beam spot or modulation of the optical beam
    • G11B7/135—Means for guiding the beam from the source to the record carrier or from the record carrier to the detector
    • G11B7/1372—Lenses
    • G11B7/1374—Objective lenses
    • 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
    • C08K9/00—Use of pretreated ingredients
    • C08K9/04—Ingredients treated with organic substances
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B7/00—Mountings, adjusting means, or light-tight connections, for optical elements
    • G02B7/008—Mountings, adjusting means, or light-tight connections, for optical elements with means for compensating for changes in temperature or for controlling the temperature; thermal stabilisation

Definitions

  • the present invention relates to a composite material and an optical element that are suitably used as a lens, a filter, a grading, an optical fiber, a flat optical waveguide, and the like.
  • An optical pickup device includes an optical element unit that irradiates an optical information recording medium with light having a predetermined wavelength emitted from a light source and receives reflected light by a light receiving element.
  • the optical element unit includes these optical element units. It has an optical element such as a lens for condensing light by a light receiving element or a reflection layer of an optical information recording medium.
  • plastic material it is preferable to apply a plastic material to the optical element of the optical pickup device described above in that it can be manufactured at low cost by means such as injection molding.
  • plastics that can be applied to optical elements copolymers of cyclic olefin and ⁇ -olefin are known (see Patent Document 1).
  • Substances containing cyclic olefin have a stable refractive index due to changes in humidity. Although the properties are excellent, it is difficult to obtain the desired effect due to the stability of the refractive index due to temperature changes.
  • Patent Document 2 It can be expected that the stability of the refractive index can be improved by suppressing linear expansion with a composite material in which a resin and inorganic particles are mixed (see Patent Document 2).
  • Patent Document 2 it has been proposed to use it as fine particles of composite oxides with other metals in order to compensate for the low refractive index, which is a drawback of silica particles that can be achieved only by suppressing the linear expansion coefficient.
  • the use of an oxide having a high hygroscopic property may significantly reduce the moisture resistance as a composite material, that is, the refractive index, depending on the humidity.
  • Patent Document 1 JP 2002-105131 A
  • Patent Document 2 Japanese Patent Laid-Open No. 2005-146042
  • An object of the present invention is to provide a composite material and an optical element that suppress a decrease in refractive index while maintaining a constant light transmittance and are excellent in heat resistance.
  • the first aspect of the present invention provides:
  • a composite material of resin and inorganic particles A composite material of resin and inorganic particles,
  • the inorganic particles are surface-modified with a compound having an adamantyl group.
  • the compound having an adamantyl group may be a compound in which an adamantyl group and a carboxyl group or a hydroxyl group are combined, and a monomer having an adamantyl group and an adamantyl group are not included! /, A monomer. It may be a copolymerized compound! /, Or a compound in which an adamantyl group is introduced into a functional group of a silane coupling agent.
  • the resin is preferably a cycloolefin resin.
  • the second aspect of the present invention is:
  • the composite material contains (1) a resin and (2) inorganic particles.
  • thermoplastic resin thermosetting resin
  • photo-curing resin etc.
  • the resin is a thermoplastic resin in terms of workability as an optical element and molding cycle time.
  • a cyclic olefin resin from the viewpoint of low hygroscopicity, which is more preferably an acrylic resin, a cyclic olefin resin, a polycarbonate resin, a polyester resin, a polyether resin, a polyamide resin or a polyimide resin.
  • examples of the resin include compounds described in JP-A-2003-73559 and the like, and preferred compounds are shown in Table 1 below. Of these resins, those having a moisture absorption rate of 0.5% or less are preferred, and those having a moisture absorption rate of 0.2% or less are more preferred.
  • the inorganic * insulator is not particularly limited, and it is possible to achieve the objective of having a small rate of change in the refractive index with temperature of the resulting composite material (hereinafter referred to as I dn / dT I).
  • Medium power of particles can be selected arbitrarily.
  • oxide fine particles, metal salt fine particles, semiconductor fine particles, and the like are preferably used. From these, those that do not cause absorption, light emission, fluorescence, or the like in the wavelength region used as an optical element are appropriately selected. It's preferable to use it.
  • the metal constituting the metal oxide is Li, Na, Mg, Al, Si, K, Ca, Sc, Ti, V, Cr, Mn, Fe, Co, Ni, Cu, Zn, Rb, Sr, Y, Nb, Zr, Mo, Ag, Cd, In, Sn, Sb, Cs, Ba, La, Ta, Hf, W, Ir, Tl, Pb, Bi, and rare earth metals
  • a metal oxide which is one or more metals selected from the above can be used.
  • silicon dioxide silicon dioxide
  • titanium oxide zinc oxide
  • aluminum oxide alumina
  • zirconium oxide Hafnium oxide
  • niobium oxide tantalum oxide
  • magnesium oxide calcium oxide
  • strontium oxide barium oxide
  • indium oxide indium oxide
  • tin oxide lead oxide
  • double oxides of these oxides lithium niobate and niobium Potassium acid
  • lithium tantalate aluminum '' Magnesium oxide (MgAl O)
  • rare earth oxides can also be used as the oxide fine particles. Specifically, scandium oxide, yttrium oxide, lanthanum oxide, cerium oxide, praseodymium oxide, neodymium oxide, samarium oxide, and sulfur oxide. Examples also include pium, gadolinium oxide, terbium oxide, dysprosium oxide, holmium oxide, erbium oxide, thulium oxide, ytterbium oxide, and lutetium oxide.
  • examples of the metal salt fine particles include carbonates, phosphates, sulfates, and the like, specifically, calcium carbonate, aluminum phosphate, and the like.
  • inorganic particles described above one kind of inorganic particles may be used, or a plurality of kinds of inorganic particles may be used in combination. By using a plurality of types of inorganic particles having different properties, the required extraordinary life can be further improved.
  • the average particle size of the inorganic particles is preferably lnm or more and lOOnm or less, more preferably lnm or more and 40nm or less. This is because when the average particle size is less than 1 nm, it is difficult to disperse the inorganic particles and the desired performance may not be obtained. Therefore, the average particle size is preferably 1 nm or more. On the other hand, if the average particle size exceeds lOOnm, The average particle diameter is preferably lOOnm or less, because the composite material is turbid and the transparency is lowered and the light transmittance may be less than 70%.
  • the average particle diameter refers to a volume average value of diameters (sphere converted particle diameters) when each particle is converted into a sphere having the same volume.
  • the inorganic particles are surface-modified with a compound having an adamantyl group!
  • a compound having an adamantyl group has, as one property, a high melting point and a high glass transition temperature, and is difficult to lower the glass transition temperature of the composite material when mixed with a resin.
  • a compound having an adamantyl group has advantages such as low moisture absorption and low heat absorption from the short wavelength region to the ultraviolet region, and is excellent in heat resistance. Sometimes, the physical properties of an optical element molded with the composite material are hardly deteriorated.
  • a compound having an adamantyl group has a weak intermolecular force when it exists on the surface of inorganic particles, and is particularly easily dispersed in a cycloolefin resin.
  • a compound having an adamantyl group is difficult to lower the refractive index of the composite material when mixed with a resin having a relatively high refractive index.
  • the compound having an adamantyl group includes (2.2.1) a compound in which an adamantyl group and a carboxy group or a hydroxyl group are bonded, (2.2.2) a monomer having an adamantyl group, and other monomers. And (2.2.3) compounds in which an adamantyl group is introduced into a functional group of a silane coupling agent.
  • the compound is a compound in which an adamantane ring represented by the following formula (1) is bonded to a carboxyl group or a hydroxyl group.
  • the compound can be obtained, for example, by copolymerizing the compounds of the above formulas (2) to (; 11) with a silane coupling agent having a reactive group.
  • a silane coupling agent having a reactive group examples include a coupling agent having a polymerizable group and mercaptopropyldimethoxysilane.
  • the manufacturing method of the composite material includes (3.1) a surface modification step of surface-modifying the inorganic particles with the compound having an adamantyl group described in each item of the above “(2. 2. 1 2. 2. 3)”. (3.2) A dispersion step of dispersing the inorganic particles in the resin after the surface modification step. (3.1) Surface modification process
  • a method of adding a surface modifier (compound having an adamantyl group) to the inorganic particle dispersion and heating and drying, or a solution of the surface modifier on the dried inorganic particle powder The method of spraying and heating, drying and processing is mentioned.
  • various dispersers and mixers are used to perform uniform surface treatment. It is preferable.
  • inorganic particles surface-modified with a compound having an adamantyl group (hereinafter referred to as “surface-modified particles”) and a resin (particularly a thermoplastic resin) are mixed to disperse the surface-modified particles in the resin.
  • surface-modified particles a compound having an adamantyl group
  • resin particularly a thermoplastic resin
  • a melt-kneading method it is preferable to use a melt-kneading method from the viewpoint of reducing the amount of volatile substances used.
  • the surface-modified particles and the resin may be added together and kneaded together! /, Or may be added in stages and kneaded. Les.
  • a method of dividing addition a method in which one component is added in several times, a method in which one component is added at a time and other components are added stepwise, or a method in which these are combined is used. be able to.
  • the addition of the surface-modified particles can be performed in a powder or agglomerated state. It is possible to add the surface-modified particles in a state of being dispersed in the liquid, but in this case, it is necessary to perform a devolatilization treatment after kneading, and the aggregated particles are dispersed into primary particles in advance. It is preferable to add after making it.
  • one kind of gas selected from the inert gases nitrogen, helium, neon, argon, krypton, and xenon, or a mixture of two or more kinds of gases is used. It is preferable to perform mixing in an atmosphere. However, even general gases such as carbon dioxide, ethylene gas, and hydrogen gas are not reactive to the material to be kneaded! /, If mixed with the inert gas described above, the gas is used. Otherwise!
  • the melt-kneading method is used in the dispersion step, it is preferable to eliminate residual oxygen as much as possible in the reaction system in the melt-kneading apparatus.
  • the oxygen content is preferably 1% or less, and more preferably 0.2% or less. This is because the resin is deteriorated by the oxidation reaction with oxygen and coloration is likely to occur.
  • melt-kneading method examples include Laboplast Mill, Brabender, and Banbury. It is possible to cite closed kneaders or batch kneaders such as a mixer, kneader and roll.
  • a continuous melt kneading apparatus such as a single screw extruder or a twin screw extruder can be used.
  • a continuous melt-kneading apparatus such as an extruder, it is possible to add the components to be added step by step from the middle of the cylinder.
  • various dispersion treatment machines such as a bead mill disperser, an ultrasonic disperser, a high-speed stirring disperser, and a high-pressure disperser are applicable. it can.
  • force S such as dinoreconia beads and glass beads, and zirconia beads are preferably used.
  • the diameter of the beads to be used is smaller, and the preferred diameter is in the range of 0.001 to 0.1 mm.
  • additives include antioxidants, light stabilizers, heat stabilizers, weathering stabilizers, stabilizers such as ultraviolet absorbers and near infrared absorbers, resin modifiers such as lubricants and plasticizers, and soft polymers.
  • anti-clouding agents such as alcoholic compounds, coloring agents such as dyes and pigments, other antistatic agents, flame retardants and the like.
  • antioxidants examples include phenolic antioxidants, phosphorus antioxidants, and phenolic antioxidants. By blending these antioxidants, it is possible to prevent the coloring and strength of the lens from being deteriorated due to oxidative deterioration during molding without reducing transparency and heat resistance.
  • 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. However, it is preferably within a range of 0.00;! To 20 parts by mass with respect to 100 parts by mass of the composite material, more preferably within a range of 0.01 to 10 parts by mass.
  • phenolic antioxidant conventionally known ones can be applied.
  • 2-t-butyl-6- (3-t-butyl-2-hydroxyl-5 described in JP-B 63-179953 Methylbenzyl) 4 methylphenyl acrylate, 2, 4 di-t-amino -6-(1-(3,5-di-amino-amino-2-hydroxyphenenole) ethenole) phenyl acrylate, etc.
  • octadecinole described in JP-A-1-168643 3- (3, 5 Di-tert-butyl-4-hydroxyphenyl) propionate and other compounds such as 2,2'-methylene bis (4-methyl-6-tert-butylphenol), 1, 1, 3 tris (2 methyl 4-hydroxyl 5-t-butylphenolino) butane, 1, 3, 5 Trimethylolene 2, 4, 6 tris (3,5-di-tert-butyl-4-hydroxybenzyl) benzene,
  • the phosphorus antioxidant is not particularly limited as long as it is a substance that is usually used in the general resin industry.
  • triphenyl phosphite diphenylisodecyl phosphite, phenyl diisodecyl phosphite.
  • tris (noyulphenyl) phosphite tris (dinoylphenyl) phosphite, and tris (2,4 di-tert-butylphenyl) phosphite are particularly preferred.
  • 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] Undecane.
  • amine-based antioxidants such as diphenylamine derivatives, nickel or zinc thiocarbamate, etc. can also be applied as antioxidants. It is.
  • a compound group having a minimum temperature at the glass transition temperature of 30 ° C or less may be blended as an anti-turbidity agent.
  • an anti-turbidity agent it is possible to prevent the occurrence of white turbidity in an environment of high temperature and high humidity for a long time by suppressing deterioration of various properties such as transparency, heat resistance and mechanical strength.
  • examples of the light resistance stabilizer include benzophenone light resistance stabilizer, benzotriazole light resistance stabilizer, hindered amine light resistance stabilizer, and the like. From the viewpoint of properties and the like, it is preferable to use a hindered amine light-resistant stabilizer (hereinafter referred to as “HALS”). As such HALS, those having a low molecular weight, medium molecular weight and high molecular weight can be appropriately selected. However, it is preferable to use low molecular weight or medium molecular weight HALS when forming a molded body from a composite material. Particularly when preparing a film-shaped molded body, high molecular weight HALS may be used. preferable.
  • HALS hindered amine light-resistant stabilizer
  • HALS with a relatively low molecular weight includes LA-77 (Asahi Denka), Tinuvin765 (CSC), Tinuvinl23 (CSC), Tinuvin440 (CSC), Tinuvinl44 (CSC), HostavinN20 (Hoechst) Manufactured) and the like.
  • Examples of medium molecular weight HALS include LA-57 (Asahi Denka), LA-52 (Asahi Denka), LA-67 (Asahi Denka), LA-62 (Asahi Denka), and the like. It is done.
  • HALS with a high molecular weight includes LA-68 (Asahi Denka), LA-63 (Asahi Denka), Ho stavinN30 (Hoechst), Chimassorb944 (CSC), Chimassorb2020 (CSC), Chimassorbl l9 (CSC), Tinuvin622 (CSC), CyasorbUV-3346 (Cytec), CyasorbUV-3529 (Cytec), Uvasil299 (GLC), etc.
  • the light transmittance of the composite material produced as described above is preferably 50% or more, more preferably 70% or more, with respect to 405 nm light when the thickness is 3 mm. More preferably, it is 85% or more.
  • the Abbe number of the composite material can be selected by selecting the surface-modified particles and the resin, it is preferable to use particles that can obtain anomalous dispersion.
  • the composite material can be effectively used for achromatization, and its value may increase.
  • the water absorption rate of the composite material is preferably 2% or less, more preferably 1% or less in an environment of a temperature of 80 ° C and a relative humidity of 90%, more preferably 0.5%. It is most preferable that
  • the water absorption is expressed in mass% unless otherwise specified.
  • the water absorption rate can be measured from a change in mass when a pre-dried composite material is stored for a certain period of time under specific high temperature and high humidity conditions.
  • the water absorption rate is calculated more accurately by measuring the amount of water contained when dried by the Karl Fischer method and measuring the mass change after the subsequent water absorption.
  • the composite material is preferably negative in the AMES test! /. This is because a positive result in the AMES test may impair the user's health, increase the environmental burden, and reduce the material stability.
  • the molding method is not particularly limited, but the melt molding method is preferable from the viewpoint of characteristics such as low birefringence, mechanical strength and dimensional accuracy in the molded product.
  • the melt molding method include press molding, extrusion molding, and injection molding. From the viewpoint of productivity, it is preferable to apply injection molding as the melt molding method.
  • injection molding as the melt molding method.
  • the molding condition is a force that is appropriately selected according to the purpose of use or molding method.
  • the temperature of the composite material in injection molding an appropriate fluidity is imparted to the resin at the time of molding to reduce the distortion of the molded product. It is preferable that the temperature is in the range of 150 ° C to 400 ° C from the viewpoints of preventing silver streaks due to thermal decomposition of the resin and effectively preventing yellowing of the molded product. More preferably, it is within the range of 200 ° C to 350 ° C, and particularly preferably within the range of 200 ° C to 330 ° C.
  • the molded product can be used in various forms such as a spherical shape, a rod shape, a plate shape, a cylindrical shape, a tubular shape, a tubular shape, a fibrous shape, a film shape or a sheet shape, and has a low birefringence, Since it is excellent in transparency, mechanical strength, heat resistance, low water absorption, etc., it can be applied to various optical components.
  • Examples of application of the optical element according to the present invention to an optical component include an optical lens and an optical prism, and specific examples thereof include an imaging system lens of a camera; a lens such as a microscope, an endoscope, and a telescope lens; Optically transmissive lenses such as eyeglass lenses; CD, CD-ROM, WORM (write-once optical disc), MO (rewritable optical disc; magneto-optical disc), MD (mini-beam printer f ⁇ lens, sensor lens, etc.
  • 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; liquid crystal display element substrates.
  • optical element according to the present invention is also suitably used as various filters, gratings, optical fibers, flat optical waveguides, and the like.
  • the optical pickup device 1 in which the optical element according to the present invention is used as the objective lens 7 will be described with reference to FIG.
  • FIG. 1 is a schematic diagram showing the internal structure of the optical pickup device 1.
  • the optical pickup device 1 includes a semiconductor laser oscillator 2 that is a light source.
  • the collimator 3, the beam splitter 4, the quarter-wave plate 5, the diaphragm 6, and the objective lens are directed in a direction away from the semiconductor laser oscillator 2. 7 are sequentially arranged.
  • a sensor lens group 8 and a sensor 9 each including two sets of lenses are sequentially disposed in a position close to the beam splitter 4 and in a direction perpendicular to the optical axis of the blue light described above.
  • the objective lens 7 as an optical element is disposed at a position facing the optical disc D, and condenses the blue light emitted from the semiconductor laser oscillator 2 on one surface of the optical disc D. It is summer.
  • Such an objective lens 7 is provided with a two-dimensional actuator 10, and the objective lens 7 is movable on the optical axis by the operation of the two-dimensional actuator 10.
  • the optical pickup device 1 emits blue light from the semiconductor laser oscillator 2 at the time of recording information on the optical disc D or at the time of reproducing information recorded on the optical disc D. As shown in FIG. 1, the emitted blue light becomes a light beam L1, which is transmitted through the collimator 3 and collimated into infinite parallel light. Transparent. Further, after passing through the aperture 6 and the objective lens 7, a condensing spot is formed on the information recording surface D2 via the protective substrate D1 of the optical disc D.
  • the light that forms the focused spot is modulated by the information pits on the information recording surface D2 of the optical disc D and reflected by the information recording surface D2. Then, the reflected light becomes a light beam L 2, is sequentially transmitted through the objective lens 7 and the diaphragm 6, is changed in polarization direction by the quarter-wave plate 5, and is reflected by the beam splitter 4. After that, astigmatism is given through the sensor lens group 8 and received by the sensor 9, and finally converted into an electric signal by being photoelectrically converted by the sensor 9.
  • the numerical aperture NA required for the objective lens 7 varies depending on the thickness dimension of the protective substrate D1 and the size of the information pit in the optical disc D. In this embodiment, it is a high-density optical disc D, and its numerical aperture is set to 0.85.
  • a dropping device, thermometer, nitrogen gas inlet tube, stirring device and reflux condenser were installed in a three-liter four-separable flask, and dehydrated isopropyl alcohol 2 Og was charged in the flask to about 80.
  • C heated with C. Mix uniformly with 10 g of methacrylolic acid, 50 g of methinoremethacrylate, 2 g of 2-methyl-2-adamantyl methacrylate, 2 g of N, N'-azobisisovaleronitryl and 20 g of isopropyl alcohol.
  • the obtained solution was dropped into the flask over 2 hours and reacted at the same temperature for 5 hours. Thereafter, 60 g of isopropyl alcohol was added and cooled to obtain a 50% by mass dispersant solution. This dispersant solution was designated as “Surface modifier 1”.
  • a dripping device, thermometer, nitrogen gas inlet tube, stirring device and reflux condenser were installed in a three-liter four-separable flask, charged with 20 g of dehydrated methyl ethyl ketone and heated at about 80 ° C. did.
  • Silane coupling agent (Shin-Etsu Chemical KBE-502) 20g, methyl methacrylate 40g, 2-methyl 2-adamantyl methacrylate 40g, N, N'-azobisisovaleronitrile 2g, isopropyl alcohol 20g
  • the homogenized solution was dropped into the flask over 2 hours and reacted at the same temperature for 5 hours. Thereafter, the solvent was removed by vacuum drying to obtain a white powder.
  • the white powder was designated as “Surface modifier 2”.
  • anion exchange resin organo amber Light IRA402BL OH AG
  • anion exchange resin organic amber Light IRA402BL OH AG
  • Example 1 3 g of 1-adamantanecarboxylic acid was added thereto and stirred well, followed by drying at 100 ° C. for 10 hours under nitrogen to obtain a white powder.
  • the white powder was melt-kneaded with 5 g of cycloolefin resin (Mitsubishi Rayon Ataripet MF) to obtain composite material 1.
  • the composite material 1 was injection molded to produce a 3 mm thick molded body, and the molded body was designated as “Sample 1”.
  • composite material 2 was obtained in the same manner as composite material 1 and sample 1.
  • the composite material 2 was injection-molded to produce a 3 mm-thick molded body, and the molded body was designated as “Sample 2”.
  • alumina Alumina TM-300 manufactured by Daimei Chemical Co., Ltd.
  • the obtained slurry was mixed with 20 g of a liquid containing 10 g of the surface modifier 1 and dried.
  • the obtained alumina particles were melt-kneaded with a cycloolefin resin (APEL5014 manufactured by Mitsui Chemicals) in the same manner as in preparation of the composite material 1 and sample 1 to obtain composite material 3.
  • the composite material 3 was injection-molded to produce a 3 mm-thick molded body, and the molded body was designated as “Sample 3”.
  • IPA 2-propanol
  • TMAH aqueous solution tetramethylammonium hydroxide aqueous solution
  • silsesquioxane was obtained by filtering off anhydrous magnesium sulfate and concentrating. This silsesquioxane was a colorless viscous liquid soluble in various organic solvents.
  • the reaction solution was washed with saturated Japanese brine until neutral, and then dehydrated with anhydrous magnesium sulfate.
  • the anhydrous magnesium sulfate was filtered and concentrated to obtain 18.77 g of the target cage-type silsesquioxane (mixture).
  • the cage-type silsesquioxane obtained was a colorless viscous liquid soluble in various organic solvents.
  • a transparent silicone resin composition (composite material) is prepared by mixing 2.5 parts by mass of hydroxycyclohexyl phenyl ketone, 1 part of the above surface modifier 2 and 50 parts of silica powder (A300 from Nippon Aerosil). 5) obtained.
  • the composite material 5 is poured into a mold so as to have a thickness of 3 mm, and cured using a 30 W / cm high-pressure mercury lamp at a cumulative exposure of 20000 mj / cm 2 to obtain a sheet-like shape having a predetermined thickness.
  • a silicon resin molding was obtained.
  • the silicon resin molding was designated as “Sample 5”.
  • Sample 8 was prepared in the same manner as in the preparation of Sample 7, except that an equivalent amount of a silane coupling agent (KBE-502 manufactured by Shin-Etsu Chemical Co., Ltd.) was used instead of the surface modifier 2.
  • a silane coupling agent KBE-502 manufactured by Shin-Etsu Chemical Co., Ltd.
  • Samples 5 and 7 had a Tg of 300 C or more and could not be measured.

Abstract

La présente invention concerne un élément optique qui élimine une dégradation d'un indice de réfraction tout en maintenant constante une transmittance de la lumière et qui est doté d'une excellente résistance thermique. Une lentille d'objectif est formée en tant qu'élément optique par moulage d'un matériau composite. Le matériau composite se compose d'une résine et de particules inorganiques, ces dernières faisant l'objet d'une modification de surface avec un composé comprenant un groupe adamantyle.
PCT/JP2007/064869 2006-08-04 2007-07-30 Matériau composite et élément optique WO2008015999A1 (fr)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010001875A1 (fr) * 2008-07-03 2010-01-07 昭和電工株式会社 Composition durcissable et matériau durci résultant
JP2012002978A (ja) * 2010-06-16 2012-01-05 Asahi Glass Co Ltd 硬化性材料の製造方法、硬化性材料および光学部材
US8349934B2 (en) 2008-12-16 2013-01-08 Showa Denko K.K. Hardening composition and hardened product thereof
WO2015146925A1 (fr) * 2014-03-28 2015-10-01 日本ゼオン株式会社 Composition de résine, article moulé en résine et constituant optique

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