WO2003065082A1 - Materiau optique - Google Patents

Materiau optique Download PDF

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Publication number
WO2003065082A1
WO2003065082A1 PCT/JP2002/010092 JP0210092W WO03065082A1 WO 2003065082 A1 WO2003065082 A1 WO 2003065082A1 JP 0210092 W JP0210092 W JP 0210092W WO 03065082 A1 WO03065082 A1 WO 03065082A1
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Prior art keywords
group
monomer
optical material
formula
meth
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PCT/JP2002/010092
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English (en)
Japanese (ja)
Inventor
Naoki Hayashi
Hiroki Katono
Katsuichi Machida
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Kureha Chemical Industry Company, Limited
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Publication of WO2003065082A1 publication Critical patent/WO2003065082A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
    • C08L33/10—Homopolymers or copolymers of methacrylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/52—Phosphorus bound to oxygen only
    • C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
    • 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

Definitions

  • the present invention relates to an optical material, and more particularly, to an optical material that exhibits absorptivity to light of a specific wavelength.
  • an optical material or an optical member having a near-infrared light absorption property utilizing a specific wavelength light absorption characteristic of copper ions for example, Japanese Patent Application Laid-Open Nos. 2001-83318 and 2001- No. 83890, Japanese Unexamined Patent Application Publication No. 2001-154015, International Publication No. 01Z77250 (WOO 1/77250)
  • the present inventors selected various phosphate ester compounds to which copper ions coordinate, and conducted studies to increase the copper ion content while considering moldability, stability, and the like as an optical component. Optical materials and optical members described in gazettes have been obtained.
  • an optical filter is particularly desired to be light and light when applied to an imaging unit or a window provided in a small device such as a portable device. Further improvement in environmental stability such as heat resistance and copper ion concentration is desired.
  • high translucency in the visible region is also important for application to the imaging unit, etc., so that it is molded into a plate-like or sheet-like member such as a filter. It is considered that a translucent resin is essential.
  • the present inventors have focused on the optical material containing the above-mentioned conventional phosphate ester compound, copper ions and a translucent resin, with an emphasis on the viewpoints of further stability and an increase in the concentration of copper ions, and repeated studies. Have been.
  • the so-called non-polymerizable phosphoric acid ester compound (non-polymeric phosphoric acid ester compound) having no polymerizable functional group was used together with copper ions.
  • concentration was increased, in some cases, a phenomenon called so-called bleed, in which dissolved substances precipitated on the material surface when left in a high-temperature, high-humidity environment for a long time, was observed.
  • so-called bleed in which dissolved substances precipitated on the material surface when left in a high-temperature, high-humidity environment for a long time, was observed.
  • the stability and high near-infrared light absorption characteristics of the optical material may be impaired.
  • polymerizable phosphate compound having a polymerizable functional group
  • non-polymeric phosphate compounds are often more useful than polymeric phosphate compounds from the viewpoints of moldability in post-processing and mold releasability during polymerization.
  • the present invention has been made in view of such circumstances, and provides an optical material having excellent absorption characteristics of specific wavelength light and moldability, and capable of maintaining high stability for a long time even in a high-temperature, high-humidity environment.
  • the purpose is to do.
  • an optical material according to the present invention is characterized in that a non-polymerizable ester phosphate compound and a copper ion are represented by the following formula (1) and a first monomer represented by the following formula (1).
  • Y 1 and Y 2 represent a hydrogen atom or a methyl group, which may be the same or different, and Z 1 is a methyl group or a carbon atom bonded to an oxygen atom of a (meth) acrylic acid skeleton Represents an organic group having 2 to 20 carbon atoms and being primary, and Z 2 represents an organic group in which the carbon atom bonded to the oxygen atom of the (meth) acrylic acid skeleton is non-primary. Show.
  • the resin containing the first monomer and the second monomer as constituents specifically means the first monomer and the second monomer. (Polymerization method, form, etc.), a copolymer of the first monomer and the second monomer, and a first monomer and a second monomer And polymer blends of each homopolymer.
  • the optical material having such a configuration since copper ions are contained in the resin containing the first and second monomers, which are both acryl-based resins having excellent translucency, as components. Excellent in visible light transmittance and near infrared light absorption.
  • a non-polymeric phosphate compound is used as the ester phosphate compound, it has excellent moldability and mold releasability during mold polymerization! / Puru.
  • the present inventors have closely monitored the bleed phenomenon, which is the conventional problem described above, and found that the bleeding optical material includes the above-mentioned Japanese Patent Application Laid-Open No. 2000-154504. It was found that whitening due to the influence of air moisture did not occur as pointed out in the above. In addition, an investigation of the precipitates revealed that it appears to contain not a copper phosphate but a phosphate ester compound and copper. In general, bleeding on the surface of a material often results from hydrolysis of a dissolved component to lower the molecular weight. When the whitening phenomenon described above occurs, precipitation of copper phosphate, which is a hydrolysis product, is usually observed in the material. From these results, it is thought that the mechanism causing the bleeding phenomenon in question is not exactly the same as that caused by normal hydrolysis, and also different from the mechanism of the bleaching phenomenon, but details are not yet clear. .
  • the bleeding is suppressed by using the first monomer and the second monomer as the constituent components of the resin.
  • the resulting resin is not particularly superior in compatibility with the copper phosphate compound as compared to the resin comprising the first monomer.
  • the resin composed of the second monomer is generally hydrophobic, but in terms of the constituent elements and molecular form, the resin composed of the first monomer has substantially the same hydrophobicity. I can say. However, as described above, no improvement in bleeding is observed with the resin comprising the first monomer alone.
  • Z 2 in the formula (2) has 3 to 10 carbon atoms, and the carbon atom bonded to the oxygen atom of the (meth) acrylic acid skeleton is secondary or tertiary. It is preferred that This not only significantly improves the moisture resistance of the optical material, but also significantly improves the solubility of the copper complex of the phosphate compound.
  • Z 21 and Z 22 each represent a C to C 8 hydrocarbon group, and z 23 , z 24 , and z 2
  • a substituted or unsubstituted isopropynole group, a tertiary butyl group, a secondary butyl group, a 1-ethylpropyl group, a tert-pentyl group, a 1-methylbutyl group, and a 1-ethylbutyl group are more preferable.
  • the second monomer is a substituted or unsubstituted cyclic hydrocarbon group having 3 to 30 carbon atoms and Z 2 in the formula (2).
  • Z 2 may be a condensed ring group or a non-condensed ring group. In this case, the moisture resistance of the optical material can be significantly improved as compared with the case where Z 2 is a substituted or unsubstituted secondary or tertiary hydrocarbon group.
  • Z 2 in the formula (2) is a substituted or unsubstituted cyclohexyl group, a pentyl group at a mouth, a cyclobutyl group, a heptinole group at a mouth mouth, a cyclooctyl group, a methylhexene group at a methyl mouth mouth, a trimethylcycline Hexyl group, decahydronaphthyl group, Or, it is a Nantyl group.
  • Z 2 in the formula (2) is a bridge. In this case, the moisture resistance of the optical material is further improved.
  • Z 2 in the formula (2) is a norpolnyl (pol) group, an isopol dinole group, a norbornylmethyl group, a dicyclopentyl group, a dicyclopentyl group, a phentyl group, an adamantyl group, a tetracycloyl group [4.4. 0 2 ' 5 .
  • a dodecinole group, a tricyclo [5.2.1.0 2 ⁇ 6 ] decal 8-yl group, and a tricyclo [5.2.1.0 2 ′ 6 ] deca 8-methyl group are preferred.
  • a compound having a borneol skeleton such as a pornyl group is used to increase TG while being a nonpolar substance.
  • TG tends to increase with an increase in polarity.
  • steric hindrance is large (bulky) and the movement of a ring in a molecule is restricted, TG acts to increase TG only by its steric effect.
  • the considerable causal relationship between the bleed prevention effect of the present invention and such a three-dimensional effect is unclear at present.
  • Z 2 in the formula (2) is a group having 6 to 30 carbon atoms and having a substituted or unsubstituted aromatic ring, the moisture resistance of the optical material is further improved, which is preferable. It is.
  • Z 2 may be a condensed ring group or a non-condensed ring group.
  • Z 2 in the formula (2) is a substituted or unsubstituted aryl group. More specifically, Z 2 in the formula (2) is a substituted or unsubstituted phenyl group or a naphthyl group. Alternatively, an anthryl group is preferable.
  • the first monomer is methyl (meth) acrylate.
  • the mass mixing ratio of the first monomer to the second monomer in the resin component is 20:80 to 90:10. If the mixing ratio of the first monomer is less than 20% by mass (the mixing ratio of the second monomer is more than 80% by mass / 0 ), the copper complex of the phosphoric acid ester compound is contained in the resin. Tends to be difficult to dissolve. On the other hand, if the mixing ratio of the first monomer is more than 90% by mass (the mixing ratio of the second monomer is less than 10% by mass), the moisture resistance tends to be not sufficiently improved.
  • the optical material of the present invention contains copper ions.
  • copper salts for supplying copper ions include copper acetate, copper acetate monohydrate, copper formate, copper stearate, copper benzoate, copper ethyl acetate, copper pyrophosphate, copper naphthenate, Copper salt anhydrides, hydrates or hydrates of organic acids such as copper citrate, or copper salt anhydrides, hydrates or hydrates of inorganic acids such as copper chloride, copper sulfate, copper nitrate, and basic copper carbonate Hydrate or copper hydroxide.
  • copper acetate, copper acetate monohydrate, copper benzoate, copper hydroxide, and basic copper carbonate are preferably used.
  • metal ions other than copper ions may be included.
  • Such other metal ions are not particularly limited, and include ions of alkali metals, alkaline earth metals, transition metals, and the like. More specifically, sodium, potassium, calcium, iron, manganese , Magnesium, nickel and the like.
  • non-polymerizable phosphate compound contained in the optical material of the present invention examples include those represented by the following formula (5). (Five)
  • R represents an organic group having no polymerizable functional group.
  • examples of such an organic group include a substituted or unsubstituted alkyl group, an oxyalkyl group, a polyoxyalkyl group, a group represented by any of the following formulas (6) to (12), and a polymerizable group such as an aryl group. Those having no functional group are mentioned.
  • n is 1 or 2, and when n is 1, R may be the same or different.
  • 13 ⁇ 4 11 ⁇ 1 17 is Arukiru group having 1 to 20 carbon atoms, Represents an aryl or aralkyl group having 6 to 20 carbon atoms (wherein a hydrogen atom bonded to a carbon atom constituting an aromatic ring is at least one substituted by an alkyl group having 1 to 6 carbon atoms or halogen) which may also be), R 21 ⁇ : 25 is a hydrogen atom or a carbon atoms represents 1-4 alkyl group (and ⁇ , R 23, R 24, when R 25 are all hydrogen atoms Except), R 3 1 and R 3 2 represents an alkylene group having 1 to 6 carbon atoms, R 4 1 represents an alkylene group having 1 to 1 0 carbon atoms, R 5 1 and R 5 2 is carbon The number represents an alkyl group of 1 to 20, m represents an integer of 1 to 6, and k represents an integer
  • Examples of the cyclic organic group include a substituted or unsubstituted cycloalkyl group, an aryl group, and an aralkyl group that do not have a polymerizable functional group.
  • Examples of the aryl group include a substituted or unsubstituted phenyl group, a naphthyl group and an anthryl group having no polymerizable functional group.
  • those substituents include those in which at least one hydrogen atom bonded to a carbon atom constituting an aromatic ring is substituted with a halogen atom or a non-polymerizable functional group having 1 to 40 carbon atoms. Can be exemplified.
  • non-polymerizable compounds containing no polymerizable functional group
  • these non-polymeric phosphate compounds can be produced by the method described in the publication or pamphlet.
  • the first monomer used in the optical material of the present invention is an acrylic resin represented by the above formula (1), wherein the organic group Z 1 bonded to the (meth) acrylic acid skeleton is a methyl group, Is a primary one in which the carbon atom bonded to the oxygen atom of the (meth) acrylic acid skeleton has 2 to 20 carbon atoms.
  • Examples of the first monomer include, but are not particularly limited to, for example, methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, n-putinole (meth) acrylate, Isoptyl (meth) acrylate, n-hexyl (meta) acrylate, neopentyl (meth) acrylate, isopentyl (meth) acrylate, n-octyl (meth) acrylate, benzyl (meth) acrylate, phenoxyshetyl (meta) ) Atarilate, glycidyl (meta) Tarylate, 2-hydroxyl (meth) atalylate, 2-hydroxypropyl (meth) atalylate, methoxypolyethylene glycolone (meth) atalylate, 2-ethylhexyl (meth) atalylate, isodecyl
  • methyl (meth) acrylate is more preferable from the viewpoints of translucency and industrial availability, and methyl methacrylate is particularly preferable in that it has a high affinity for a non-polymerized ester phosphate compound.
  • the second monomer constituting the resin used in the optical material of the present invention is an acrylic resin monomer represented by the above formula (2), and is an organic group bonded to the (meth) acrylic acid skeleton.
  • Z 2 has a non-primary carbon atom bonded to the oxygen atom of the (meth) acrylic acid skeleton.
  • Equation (2) that of secondary or tertiary chain hydrocarbon group of Z 2 force carbon number is 3-2 0 and a substituted or unsubstituted in, for example, Z 2 is a substituted or unsubstituted chain It is preferable that the carbon atom bonded to the oxygen atom of the (meth) acrylic acid skeleton does not form a ring even if it has a cyclic hydrocarbon group or a ring.
  • the use of such a second monomer having Z 2 can significantly improve the solubility of the copper complex of the phosphate compound. In this case, if the carbon number of Z 2 exceeds 20, the compatibility tends to be insufficient.
  • Z 2 is a substituted or unsubstituted isopropyl group, tertiary butyl group, secondary butyl group, 1-ethylpropyl group-tertiary pentyl group, 1 More preferably, it is a monomethylbutyl group or a monoethylbutyl group.
  • Z 2 is an isopropyl group or a tertiary butyl group, that is, the second monomer is, for example, isopropyl methacrylate or (14) represented by the following formula (13) or (14), respectively.
  • Particularly preferred is tert-butyl methacrylate or the like.
  • tertiary butyl methacrylate Some of such second monomers are commercially available, such as tertiary butyl methacrylate.For example, various alcohols are reacted with (meth) acrylic acid chloride in the presence of triethylamine. Can be obtained by
  • Z 2 in the formula (2) is a substituted or unsubstituted cyclic hydrocarbon group having 3 to 30 carbon atoms and Z 2 is a condensed ring group or a non-condensed ring group. (That is, it may be a multi-membered ring or a polycyclic ring).
  • Z 2 is a substituted or unsubstituted secondary or tertiary hydrocarbon group. If the number of carbon atoms exceeds 30, the compatibility becomes insufficient and the resin body may become cloudy.
  • Z 2 is a substituted or unsubstituted cyclohexyl group, cyclopentyl group, cyclobutyl group, cycloheptyl group, cyclooctyl group, methylcyclohexyl group, trimethylcyclohexyl group, decahydronaphthyl group And a cycloalkyl group such as a nantyl group.
  • Z 2 is a cyclohexyl group, that is, the second monomer is, for example, cyclohexyl represented by the following formula (15). Particularly preferred is methacrylate.
  • Such a second monomer may be a commercially available product such as cyclohexyl methacrylate, etc.
  • the second monomer can be produced by the following method. That is, it can be obtained by reacting various alcohols with (meth) acrylic acid chloride in the presence of triethylamine.
  • 2-decahydronaphthyl (meth) tarylate is obtained by reacting 2-decahydronaphthol with a (meth) acrylic acid methacrylate in the presence of triethylamine, extracting with an organic solvent such as ether, and then depressurizing. It can be obtained by distillation.
  • Z 2 in the formula (2) is a bridging body, that is, the second monomer is a bridging compound.
  • a norpoluel (bonyl) group an isobonolenyl group, a norbornylmethyl group, a dicyclopentenetinole group, a dicyclopentanyl group, a phentyl group, an adamantyl group, a tetracyclo [4.4 . 0 2,5. 17,10]
  • Dodeshinore group tricyclo [5.2.1.0 2 '6] dec-one 8-I group, tricyclo [5.2.1.0 2. 6] Deka
  • the second monomer is, for example, isobornyl methacrylate represented by the following formula (16) Is particularly preferred.
  • Some of such second monomers can be obtained as a commercial product such as isopolnyl methacrylate, etc., for example, as described above, various alcohols can be obtained in the presence of triethylamine. It can also be obtained by reacting with (meth) acrylic acid chloride.
  • Z 2 in the formula (2) may be a group having 6 to 30 carbon atoms and having a substituted or unsubstituted aromatic ring, and may be a condensed ring group or a non-condensed ring group. Good. Also in this case, the moisture resistance of the optical material can be improved as in the case of the alicyclic group represented by the formula (3) such that Z 2 is a cyclohexyl group or the like.
  • Z 2 in the formula (2) is a substituted or unsubstituted aryl group, and more specifically, Z 2 in the formula (2) is a substituted or unsubstituted phenyl group, a naphthyl group, Examples include an anthryl group, a phenanthryl group, and a phenaleryl group.
  • Such a second monomer is synthesized by, for example, a condensation reaction between (meth) acrylic acid and phenol as described in JP-A-63-57554 for fuel methacrylate. It is possible.
  • the amount of the second monomer used in the present invention is not particularly limited, but may vary depending on the type of the first monomer and / or the type of the second monomer. It is useful that the mass mixing ratio of the body and the second monomer is from 20:80 to 90:10.
  • the mixing ratio of the first monomer is less than 20% by mass (the mixing ratio of the second monomer is more than 80% by mass), the copper complex of the phosphate ester compound dissolves in the resin. It tends to be difficult.
  • the mixing ratio of the first monomer is more than 90% by mass (the mixing ratio of the second monomer is less than 10% by mass)
  • the moisture resistance tends to be not sufficiently improved. Therefore, by setting such a suitable mixing ratio, the concentration of copper ions can be sufficiently and surely increased, and a more stable optical material having excellent moisture resistance can be easily realized.
  • the optical material of the present invention having such a configuration is capable of absorbing the above-described specific wavelength light. Excellent characteristics such as yield characteristics, moldability, and stability in high temperature and high humidity environments can be achieved, so it can be used as various functional materials in various forms (use forms) or in combination with various functional materials Thus, it can be suitably used for various applications.
  • Examples of such a form include a coat shape, a sheet shape, a disk shape, a fiber shape, a film shape, a prism shape, a lens shape, a columnar shape, a plate shape, a film shape, and the like. It can be used in the form of an adhesive, an adhesive, or a molded article.
  • various functional materials include coating materials (agents), hard coat materials (agents), bandpass functional materials such as low-pass filters, diffraction grating materials, electromagnetic wave shielding materials for EMI removal, birefringent plates, coloring agents, Light stabilizer, antioxidant, ultraviolet absorber, crystal, antistatic agent, heat stabilizer, release agent, polymerization regulator, other optical materials, antireflective material (antireflective coating material), depolarizing plate, conductive
  • Various applications include CCD lid materials, PDP front panel and other display front panels, display front filters, goggles, lenses such as glasses, optical fibers, optical switches, optical filters, optical low-pass filters, and visibility correction. Examples include filters, photometric filters, imaging filters, window materials, agricultural covering materials, lighting equipment, and the like.
  • phosphate compound 90.1 g of 1-methoxy-2-propanol was dissolved in 18 Om1 of toluene, and cooled to 5 ° C or lower. 4 g was added little by little, and the whole amount was added by stirring, and then stirring was continued for 15 hours. Then, the mixture was stirred and mixed at 60 ° C for 8 hours, and after adding 7 ml of water, the temperature was raised to 100 ° C and the 3B temple was agitated. After completion of the reaction, toluene and unreacted 1-methoxy-2-propanol were distilled off under reduced pressure to obtain 124 g of a slightly yellow viscous oily phosphate compound.
  • each of them is housed in an open, and at a constant temperature of 40 ° C for 3 hours,
  • a resin plate was manufactured in the same manner as in Example 1, except that the resin composed of MMA as the first monomer was used alone as the resin component.
  • a resin plate was manufactured in the same manner as in Example 1 except that the resin consisting of the second monomer, 0 and ⁇ , was used alone as the resin component.
  • the resin plate that showed good results in the moisture resistance test (marked ⁇ or ⁇ in Table 1) was visually observed after standing at 800 ° C in a dry environment for 100 hours. Bleeding and turbidity were observed. Spectrophotometry was performed using the above spectrophotometer “U-400”. As a result, no abnormality such as turbidity or bleeding was observed in any of the resin plates subjected to the test.
  • phosphate ester copper compound Table 2 shows the solubility of the product and the moisture resistance and heat resistance when the concentration of the copper phosphate ester compound in the resin plate is 18.875 mass%.
  • a resin plate was prepared in the same manner as in Example 1 except that the monomers represented by the following formulas (19) to (21) (Comparative Examples 3, 4, and 5) were used as the second monomer. Was made.
  • the monomers of the formulas (19) to (21) are respectively a bifunctional (meth) acrylate and a (meth) acrylate having Z 2 in the second monomer being a lower alkyl, It belongs to fluorinated (meta) acrylate.
  • the resin containing the first monomer and the second monomer as host components for the non-polymerized phosphate compound and the copper ion host resin By using, it is possible to achieve excellent absorption characteristics of specific wavelength light unique to copper ions and moldability, and to maintain high stability for a long time even in a high-temperature and high-humidity environment.

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

Abstract

Cette invention concerne un matériau optique comprenant d'une part une résine constituée d'unités dérivées d'un premier monomère tel que le méthacrylate de méthyle et d'un second monomère tel que le méthacrylate d'isobornyle ou le méthacrylate t-butyle, et d'autre part, contenus dans la résine, un composé ester phosphorique non polymérisé ainsi que des ions cuivre. Ce matériau optique présente d'excellentes propriétés en matière d'absorption de lumières présentant des longueurs d'onde spécifiques et en matière d'aptitude au moulage. Ce matériau optique peut rester très stable pendant une durée prolongée, même dans un environnement à haute température et à haut degré d'humidité.
PCT/JP2002/010092 2002-01-25 2002-09-27 Materiau optique WO2003065082A1 (fr)

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JP2002-17439 2002-01-25
JP2002017439A JP4071003B2 (ja) 2002-01-25 2002-01-25 光学材料

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WO2005087870A1 (fr) * 2004-03-10 2005-09-22 Kureha Corporation Agent solubilisant et composition contenant celui-ci

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CN101520524B (zh) * 2008-02-25 2011-03-23 财团法人工业技术研究院 光扩散膜
JP5331361B2 (ja) * 2008-03-31 2013-10-30 株式会社クレハ 銅塩組成物、並びに、これを用いた樹脂組成物、赤外吸収膜及び光学部材
KR101477847B1 (ko) * 2011-09-16 2014-12-31 주식회사 엘지화학 광학필름용 아크릴계 공중합체 및 이를 이용하여 형성된 광학필름
JP2014026070A (ja) * 2012-07-26 2014-02-06 Fujifilm Corp 近赤外線吸収性組成物、これを用いた近赤外線カットフィルタ及びその製造方法、並びに、カメラモジュール及びその製造方法
JP6016518B2 (ja) * 2012-08-21 2016-10-26 富士フイルム株式会社 近赤外線吸収剤、近赤外線吸収性組成物、これらを用いた近赤外線カットフィルタ及びその製造方法、カメラモジュール及びその製造方法、ならびに、近赤外線吸収剤の製造方法
JPWO2019244589A1 (ja) * 2018-06-19 2021-07-15 コニカミノルタ株式会社 近赤外線吸収性組成物、近赤外線吸収性膜及び固体撮像素子用イメージセンサー

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JPH10152598A (ja) * 1996-11-22 1998-06-09 Sumitomo Chem Co Ltd 近赤外吸収樹脂組成物および材料
JP2000007871A (ja) * 1998-06-23 2000-01-11 Kureha Chem Ind Co Ltd 樹脂組成物およびその製造法、光学フィルターおよびこれを備えた装置、熱線吸収フィルター、光ファイバーおよび眼鏡レンズ

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JPS5770146A (en) * 1980-10-17 1982-04-30 Mitsubishi Rayon Co Ltd Methacrylate resin material for optical filter and production thereof
JPH10152598A (ja) * 1996-11-22 1998-06-09 Sumitomo Chem Co Ltd 近赤外吸収樹脂組成物および材料
JP2000007871A (ja) * 1998-06-23 2000-01-11 Kureha Chem Ind Co Ltd 樹脂組成物およびその製造法、光学フィルターおよびこれを備えた装置、熱線吸収フィルター、光ファイバーおよび眼鏡レンズ

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005087870A1 (fr) * 2004-03-10 2005-09-22 Kureha Corporation Agent solubilisant et composition contenant celui-ci
JPWO2005087870A1 (ja) * 2004-03-10 2008-01-24 株式会社クレハ 可溶化剤及びこれを含有する組成物
US7781519B2 (en) 2004-03-10 2010-08-24 Kureha Corporation Solubilizer and composition containing same

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