Classifications

• • 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
  • C08K5/16—Nitrogen-containing compounds
  • C08K5/34—Heterocyclic compounds having nitrogen in the ring
  • C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
  • C08K5/3415—Five-membered rings
  • C08K5/3417—Five-membered rings condensed with carbocyclic rings
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
  • C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
  • C08G61/04—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms
  • C08G61/06—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds
  • C08G61/08—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds of carbocyclic compounds containing one or more carbon-to-carbon double bonds in the ring
• • 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
  • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
  • C08K5/0041—Optical brightening agents, organic pigments
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
  • C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
  • C08L23/04—Homopolymers or copolymers of ethene
  • C08L23/08—Copolymers of ethene
  • C08L23/0807—Copolymers of ethene with unsaturated hydrocarbons only containing four or more carbon atoms
  • C08L23/0823—Copolymers of ethene with unsaturated hydrocarbons only containing four or more carbon atoms with aliphatic cyclic olefins
• • 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
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D165/00—Coating compositions based on macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Coating compositions based on derivatives of such polymers
• • 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
  • 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
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
  • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
  • C08G2261/33—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain
  • C08G2261/332—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing only carbon atoms
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
  • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
  • C08G2261/33—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain
  • C08G2261/332—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing only carbon atoms
  • C08G2261/3324—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing only carbon atoms derived from norbornene
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
  • C08G2261/40—Polymerisation processes
  • C08G2261/41—Organometallic coupling reactions
  • C08G2261/418—Ring opening metathesis polymerisation [ROMP]

Definitions

• the present invention relates to a resin composition for forming an optical component, a molded article, and an optical component.
• colors different from the original may occur as color bleeding due to chromatic aberration of the optical system that forms an optical image of the subject on the imaging device.
• visible light in a wavelength band close to the ultraviolet region and the infrared region tends to cause color fringing.
• Such color fringing can be suppressed to some extent by combining multiple lenses with different dispersion characteristics, but with the recent increase in resolution of imaging devices (especially smartphone cameras), the demand for improvement of color fringing has increased. Therefore, it is becoming difficult to sufficiently suppress color fringing only by combining lenses.
• Another issue is the phenomenon known as ghosting, in which a non-existent image of light appears in the image due to stray light that is diffusely reflected by the lens surface or the surface of the infrared cut filter between the lens and the sensor and enters the sensor as stray light. It is
• color fringing can be improved by coloring the lens and absorbing light in a wavelength band close to the ultraviolet and infrared regions.
• part of the light diffusely reflected on the surface of the lens and the surface of the infrared cut filter between the lens and the sensor is absorbed by the lens, so it is thought that the ghost is improved.
• the color of the lens is too dark, the entire image will be colored, so it is required that the absorption of visible light other than the wavelength band near the ultraviolet region and the infrared region be as small as possible.
• Patent Document 1 discloses a transparent resin substrate containing a near-infrared absorbing dye and a near-infrared reflective film formed on at least one surface of the substrate, and satisfies the requirements for transmittance in a specific wavelength region. A satisfying optical filter is disclosed. The document describes the use of a cyclic olefin and a squarylium dye.
• Patent Document 2 discloses that the object side surface and the image side of the object side surface and the image side from the object side to the image side include at least one long wavelength absorption component made of a plastic material and homogeneously mixed in the plastic material and having refractive power.
• an optical imaging lens comprising at least one optical lens in which at least one of the side surfaces is aspherical, wherein the optical lens containing the long-wavelength absorbing component satisfies a requirement for transmittance in a specific wavelength region.
• This document describes a cyclic olefin resin as the resin and a squarylium dye as the dye.
• the inventors have found that the above problems can be solved by combining a cyclic olefin-based polymer with a specific dye to obtain a predetermined transmission characteristic, and have completed the present invention. That is, the present invention can be shown below.
• a resin composition for forming an optical component comprising
• the cyclic olefin polymer (A) contains at least one selected from copolymers of ethylene or ⁇ -olefins and cyclic olefins, and ring-opening polymers of cyclic olefins,
• the molded article made of the resin composition for forming an optical component satisfies all of the following conditions (1) to (3) when the thickness is such that the transmittance of light with a wavelength of 700 nm is 30%.
• a resin composition for forming an optical component is
• the average transmittance at a wavelength of 300 to 400 nm is 40% or less (2)
• the average transmittance at a wavelength of 500 to 600 nm is 70% or more (3)
• the transmittance at a wavelength of 650 nm is 60% or more [2]
• a resin composition for forming an optical component comprising
• the cyclic olefin polymer (A) contains at least one selected from copolymers of ethylene or ⁇ -olefins and cyclic olefins, and ring-opening polymers of cyclic olefins,
• a resin composition for forming an optical component characterized in that a molded article having a thickness of 1 mm made of the resin composition for forming an optical component satisfies all of the following conditions (1) to (5).
• At least one of the dyes (B) is a squarylium dye, according to [1] or [2];
• R 1 to R 10 each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 1 to 20 carbon atoms, an alkenyl group having 1 to 20 carbon atoms, -20 halogenoalkyl groups, 1-20 carbon alkoxy groups, 1-20 carbon halogenoalkoxy groups, 1-20 carbon alkylthio groups, 1-20 carbon alkoxyalkyl groups, 1-20 carbon atoms alkoxyalkoxyalkyl group, halogenoalkoxyalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted aryl group, substituted or unsubstituted aralkyl group, substituted or unsubstituted amino group, substituted or unsubstituted acyl group, substituted Alternatively, it represents an unsubstituted aryloxy group, a substituted or un
• R 1 to R 10 each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 1 to 20 carbon atoms, an alkenyl group having 1 to 20 carbon atoms, -20 halogenoalkyl groups, 1-20 carbon alkoxy groups, 1-20 carbon halogenoalkoxy groups, 1-20 carbon alkylthio groups, 1-20 carbon alkoxyalkyl groups, 1-20 carbon atoms alkoxyalkoxyalkyl group, halogenoalkoxyalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted aryl group, substituted or unsubstituted aralkyl group, substituted or unsubstituted amino group, substituted or unsubstituted acyl group, substituted Alternatively, it represents an unsubstituted aryloxy group, a substituted or un
• An optical component comprising the molded article according to [10].
• the optical component according to [11] which is a lens.
• the average transmittance at a wavelength of 300 to 400 nm is 40% or less
• the average transmittance at a wavelength of 500 to 600 nm is 70% or more
• the transmittance at a wavelength of 650 nm is 60% or more [14] 2] including a molded body obtained by molding the resin composition for forming an optical component according to A lens characterized by satisfying all of the following conditions (1) to (5).
• Average transmittance of 40% or less at wavelengths of 300 to 400 nm (2) Average transmittance of 70% or more at wavelengths of 500 to 600 nm (3) Transmittance of 60% or more at wavelengths of 650 nm (4) Wavelength The minimum value of transmittance from 660 nm to 750 nm is 30% or less (5) Internal haze is 1.0% or less
• the occurrence of color fringing such as purple fringing is sufficiently suppressed, and further, while maintaining the light transmittance that can be used as an optical member for imaging and the light absorption at a specific wavelength, it is sufficiently even after the passage of time.
• a resin composition for forming an optical part which gives a molded article capable of maintaining a high light transmittance.
• the resin composition of the present embodiment contains a cyclic olefin polymer (A) and one or more dyes (B). Each component will be described in detail below.
• the cyclic olefin-based polymer (A) is a polymer having a structural unit derived from a cyclic olefin as an essential structural unit.
• the cyclic olefin polymer (A) includes at least one selected from cyclic olefin copolymers (A-1) and ring-opened cyclic olefin polymers (A-2). By including these, it is possible to further improve the heat resistance and improve the moldability while maintaining a good balance between the transparency and the refractive index of the resulting optical component.
• Cyclic olefin copolymer (A-1) examples include copolymers of ethylene or ⁇ -olefin and cyclic olefin.
• the cyclic olefin compound constituting the cyclic olefin-based copolymer (A-1) is not particularly limited, and examples thereof include cyclic olefin monomers described in paragraphs 0037 to 0063 of WO 2006/0118261. .
• the cyclic olefin copolymer (A-1) preferably has a structural unit (a) and a structural unit (b) from the viewpoint of further improving the optical properties of the resulting optical component.
• Optical properties refer to properties such as transparency and refractive index of optical components.
• Structural unit (a) A structural unit derived from at least one olefin represented by the following general formula (I).
• R 300 represents a hydrogen atom or a linear or branched hydrocarbon group having 1 to 29 carbon atoms.
• Structural unit (b) A structural unit derived from at least one cyclic olefin selected from the group consisting of the following general formula (II), the following general formula (III), and the following general formula (IV).
• R 61 to R 78 and R a1 and R b1 may be the same or different, and may be a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, or a halogenated group having 1 to 20 carbon atoms. It is an alkyl group, a cycloalkyl group having 3 to 15 carbon atoms, or an aromatic hydrocarbon group having 6 to 20 carbon atoms.
• R 75 to R 78 may combine with each other to form a monocyclic or polycyclic ring.
• x and d are each independently an integer of 0 or 1 or more.
• y and z are each independently an integer from 0 to 2;
• R 81 to R 99 which may be the same or different, are a hydrogen atom, a halogen atom, an aliphatic hydrocarbon group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or a cycloalkyl group having 3 to 15 carbon atoms; It is an aromatic hydrocarbon group or an alkoxy group having 6 to 20 carbon atoms.
• R 100 and R 101 may be the same or different and represent a hydrogen atom or a hydrocarbon group having 1 to 5 carbon atoms.
• f is 1 ⁇ f ⁇ 18.
• the olefin monomer which is one of the raw materials for copolymerization of the cyclic olefin copolymer (A-1) according to the present embodiment, undergoes addition polymerization to form the structural unit represented by the general formula (I).
• the structural unit represented by the general formula (I) undergoes addition polymerization to form the structural unit represented by the general formula (I).
• an olefin monomer represented by the following general formula (Ia) corresponding to the above general formula (I) is used.
• R 300 represents a hydrogen atom or a linear or branched hydrocarbon group having 1 to 29 carbon atoms.
• Examples of the olefin monomer represented by the general formula (Ia) include ethylene, propylene, 1-butene, 1-pentene, 1-hexene, 3-methyl-1-butene, 3-methyl-1-pentene, 3 -ethyl-1-pentene, 4-methyl-1-pentene, 4-methyl-1-hexene, 4,4-dimethyl-1-hexene, 4,4-dimethyl-1-pentene, 4-ethyl-1-hexene , 3-ethyl-1-hexene, 1-octene, 1-decene, 1-dodecene, 1-tetradecene, 1-hexadecene, 1-octadecene, 1-eicosene and the like.
• ethylene and propylene are preferred, and ethylene is particularly preferred, from the viewpoint of obtaining an optical component having superior heat resistance, mechanical properties and optical properties.
• Two or more kinds of olefin monomers represented by the general formula (Ia) may be used.
• the ratio of the olefin-derived structural unit (a) is preferably 5 mol% or more and 95 mol% or less, when the total of the structural units constituting the cyclic olefin copolymer (A-1) is 100 mol%. It is preferably 20 mol % or more and 90 mol % or less, more preferably 40 mol % or more and 80 mol % or less, and particularly preferably 50 mol % or more and 70 mol % or less.
• the proportion of the olefin-derived structural unit (a) can be measured by 13 C-NMR.
• the cyclic olefin monomer which is one of the raw materials for copolymerization of the cyclic olefin copolymer (A-1), is subjected to addition polymerization to give the general formula (II), the general formula (III), or the general formula (IV). It forms the structural unit (b) derived from the represented cyclic olefin. Specifically, cyclic compounds represented by general formulas (IIa), (IIIa), and (IVa) corresponding to the general formula (II), the general formula (III), and the general formula (IV), respectively Olefin monomers are used.
• u is 0 or 1
• v is 0 or a positive integer, preferably an integer of 0 or more and 2 or less, more preferably 0 or 1
• w is 0 or 1
• R 61 to R 78 , R a1 and R b1 may be the same or different, and may be a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, a halogenated alkyl group having 1 to 20 carbon atoms, It is a cycloalkyl group having 3 to 15 carbon atoms or an aromatic hydrocarbon group having 6 to 20 carbon atoms, and R 75 to R 78 may combine with each other to form a monocyclic or polycyclic ring.
• x and d are each independently an integer of 0 or 1 or more, preferably an integer of 0 or more and 2 or less, more preferably 0 or 1
• y and z are each independently 0, 1 or 2
• R 81 to R 99 which may be the same or different, are a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, or a cycloalkyl group having 3 to 15 carbon atoms.
• R 100 and R 101 may be the same or different and each represents a hydrogen atom or a hydrocarbon group having 1 to 5 carbon atoms, and f is 1 ⁇ f ⁇ 18.
• a cyclic olefin copolymer By using the olefin monomer represented by the general formula (Ia) or the cyclic olefin monomer represented by the general formula (IIa), (IIIa) or (IVa) as a copolymerization component, a cyclic olefin copolymer By further improving the solubility of (A-1) in a solvent, the moldability is improved and the product yield is improved.
• bicyclo-2-heptene derivatives bicyclohept-2-ene derivatives
• tricyclo-3-decene derivatives tricyclo-3-undecene derivatives
• tetracyclo-3-dodecene derivatives pentacyclo-4-pentadecene derivatives
• pentacyclo pentadecadiene derivative pentacyclo-3-pentadecene derivative
• pentacyclo-4-hexadecene derivative pentacyclo-3-hexadecene derivative, hexacyclo-4-heptadecene derivative, heptacyclo-5-eicosene derivative, heptacyclo-4-eicosene derivative, heptacyclo-5 -heneicosene derivatives, octacyclo-5-docosene derivatives, nonacyclo-5-pentacosene derivatives, nonacyclo-6-hexa
• Examples of the cyclic olefin monomer represented by the general formula (IIa) include bicyclo[2.2.1]-2-heptene (also referred to as norbornene), tetracyclo[4.4.0.1 2,5 . 1 7,10 ]-3-dodecene (also called tetracyclododecene) is preferably used, and tetracyclo[4.4.0.1 2,5 . 1 7,10 ]-3-dodecene is more preferably used. Since these cyclic olefins have a rigid ring structure, there is an advantage that the elastic modulus of the copolymer and the optical parts can be easily maintained.
• the ratio of the structural unit (b) derived from the cyclic olefin is preferably 5 mol% or more when the total of the structural units constituting the cyclic olefin copolymer (A-1) according to the present embodiment is 100 mol%. It is 95 mol % or less, more preferably 10 mol % or more and 80 mol % or less, still more preferably 20 mol % or more and 60 mol % or less, and particularly preferably 30 mol % or more and 50 mol % or less.
• the copolymerization type of the cyclic olefin copolymer (A-1) according to the present embodiment is not particularly limited, examples thereof include random copolymers and block copolymers.
• the cyclic olefin copolymer (A-1) according to the present embodiment is excellent in optical properties such as transparency, refractive index and birefringence, and can provide highly accurate optical parts. As, it is preferable to use a random copolymer.
• cyclic olefin copolymer (A-1) As the cyclic olefin copolymer (A-1) according to the present embodiment, ethylene and tetracyclo[4.4.0.1 2,5 . 1 7,10 ]-3-dodecene and random copolymers of ethylene and bicyclo[2.2.1]-2-heptene, preferably ethylene and tetracyclo[4.4. 0.1 2,5 . A random copolymer with 1 7,10 ]-3-dodecene is more preferred.
• the copolymer (A-1) according to the present embodiment may be used alone or in combination of two or more.
• the copolymer (A-1) for example, JP-A-60-168708, JP-A-61-120816, JP-A-61-115912, JP-A-61-115916 JP, JP-A-61-271308, JP-A-61-272216, JP-A-62-252406, JP-A-62-252407, etc. Produced by appropriately selecting conditions according to the method can do.
• the cyclic olefin-based copolymer (A-1) has a structural unit (II) represented by the general formula (II) and a structural unit (D) derived from a cyclic olefin having an aromatic ring, and the structural unit (II) does not contain an aromatic ring and the cyclic olefin having the above aromatic ring is a compound represented by the following formula (D-1), a compound represented by the following formula (D-2), a compound represented by the following formula (D-3 ) preferably contains one or more selected from the group consisting of the compounds represented by the formulas.
• n and q are each independently 0, 1 or 2.
• R 1 to R 17 are each independently a hydrogen atom, a halogen atom other than a fluorine atom, or a hydrocarbon group having 1 to 20 carbon atoms optionally substituted with a halogen atom other than a fluorine atom, and R 10 to One of R 17 is a bond.
• R 10 and R 11 , R 11 and R 12 , R 12 and R 13 , R 13 and R 14 , R 14 and R 15 , R 15 and R 10 are bonded to each other to form a monocyclic ring. Alternatively, it may form a polycyclic ring.
• R10 and R11 , R11 and R17 , R17 and R17 , R17 and R12 , R12 and R13 , R13 and R14 , R14 and R15 , R 15 and R 16 , R 16 and R 16 , R 16 and R 10 may be bonded to each other to form a monocyclic or polycyclic ring, and the monocyclic or polycyclic ring has a double bond. and the monocyclic ring or the polycyclic ring may be an aromatic ring.
• n and m are each independently 0, 1 or 2
• q is 1, 2 or 3.
• R 28 and R 28 , R 28 and R 29 , R 29 and R 30 , R 30 and R 31 , R 31 and R 31 are bonded to each other to form a monocyclic or polycyclic ring.
• the monocyclic ring or the polycyclic ring may have a double bond, and the monocyclic ring or the polycyclic ring may be an aromatic ring.
• R 32 to R 39 are each independently substituted with a hydrogen atom, a halogen atom other than a fluorine atom, or a halogen atom other than a fluorine atom.
• is a hydrocarbon group having 1 to 20 carbon atoms which may be Further, when q 1, R 36 and R 37 , R 37 and R 38 , R 38 and R 39 may combine with each other to form a monocyclic or polycyclic ring.
• R 36 and R 36 , R 36 and R 37 , R 37 and R 38 , R 38 and R 39 , R 39 and R 39 are bonded to each other to form a monocyclic or polycyclic ring.
• the monocyclic ring or the polycyclic ring may have a double bond, and the monocyclic ring or the polycyclic ring may be an aromatic ring.
• hydrocarbon groups having 1 to 20 carbon atoms of (D-1) to (D-3) each independently include, for example, an alkyl group having 1 to 20 carbon atoms, a cyclo Examples include alkyl groups and aromatic ring hydrocarbon groups. More specifically, alkyl groups include methyl, ethyl, propyl, isopropyl, amyl, hexyl, octyl, decyl, dodecyl and octadecyl groups. A cyclohexyl group etc. are mentioned as a cycloalkyl group.
• aromatic hydrocarbon group examples include aryl groups such as phenyl group, tolyl group, naphthyl group, benzyl group and phenylethyl group, and aralkyl groups. These hydrocarbon groups may be substituted with halogen atoms other than fluorine atoms.
• the content of the structural unit (D) derived from is preferably 5 mol% or more and 95 mol% or less, more preferably 10 mol% or more and 90 mol% or less, still more preferably 20 mol% or more and 80 mol% or less, still more It is preferably 30 mol % or more and 80 mol % or less, and still more preferably 40 mol % or more and 78 mol % or less.
• the content of structural unit (II) and structural unit (D) can be measured by, for example, 1 H-NMR or 13 C-NMR.
• Ring-opening polymer of cyclic olefin (A-2) As the cyclic olefin polymer (A), a ring-opened cyclic olefin polymer (A-2) can be used.
• Examples of the ring-opening polymer of cyclic olefin (A-2) include ring-opening polymers of norbornene-based monomers and ring-opening polymers of norbornene-based monomers and other monomers capable of ring-opening copolymerization thereof. Ring polymers, hydrides thereof, and the like are included.
• norbornene-based monomers include, for example, bicyclo[2.2.1]hept-2-ene (common name: norbornene) and derivatives thereof (having a substituent on the ring), tricyclo[ 4.3.01 , 6 . 1 2,5 ]deca-3,7-diene (common name dicyclopentadiene) and its derivatives, 7,8-benzotricyclo[4.3.0.1 2,5 ]dec-3-ene (common name methanotetrahydrofluorene: 1,4-methano-1,4,4a,9a-tetrahydrofluorene) and its derivatives, tetracyclo[4.4.0.1 2,5 . 1 7,10 ]-3-dodecene (common name: tetracyclododecene) and derivatives thereof, and the like.
• substituents on the ring of these derivatives include alkyl groups, alkylene groups, vinyl groups, alkoxycarbonyl groups, and alkylidene groups.
• the substituent can have 1 or 2 or more.
• Derivatives having a substituent on such a ring include, for example, 8-methoxycarbonyl-tetracyclo[4.4.0.1 2,5 . 1 7,10 ]dodeca-3-ene, 8-methyl-8-methoxycarbonyl-tetracyclo[4.4.0.1 2,5 . 1 7,10 ]dodeca-3-ene, 8-ethylidene-tetracyclo[4.4.0.1 2,5 . 1 7,10 ]dodeca-3-ene and the like.
• These norbornene-based monomers may be used alone or in combination of two or more.
• a ring-opening polymer of a norbornene-based monomer, or a ring-opening polymer of a norbornene-based monomer and other monomers capable of ring-opening copolymerization with the monomer component is prepared by a known ring-opening polymerization. It can be obtained by polymerization in the presence of a catalyst.
• the ring-opening polymerization catalyst includes, for example, a metal halide such as ruthenium and osmium, a nitrate or an acetylacetone compound, and a reducing agent; , an organoaluminum compound; and the like.
• a metal halide such as ruthenium and osmium, a nitrate or an acetylacetone compound, and a reducing agent
• an organoaluminum compound an organoaluminum compound
• Examples of other monomers capable of ring-opening copolymerization with norbornene-based monomers include monocyclic cyclic olefin-based monomers such as cyclohexene, cycloheptene, and cyclooctene.
• a hydride of a ring-opening polymer of a norbornene-based monomer, or a hydride of a ring-opening polymer of a norbornene-based monomer and another monomer capable of ring-opening copolymerization thereof is usually the above ring-opening It can be obtained by adding a known hydrogenation catalyst containing a transition metal such as nickel or palladium to a polymerization solution of the polymer to hydrogenate the carbon-carbon unsaturated bond.
• the ring-opening polymer (A-2) of a cyclic olefin according to the present embodiment is, for example, JP-A-60-26024, JP-A-9-268250, JP-A-63-145324, JP-A-2001. It can be produced by appropriately selecting conditions according to the method disclosed in JP-A-72839 or the like.
• the cyclic olefin ring-opening polymer (A-2) according to the present embodiment may be used alone or in combination of two or more.
• the content of the cyclic olefin polymer (A) according to the present embodiment is preferably 80% by mass or more and 99% by mass or less, more preferably 90% by mass or more and 99% by mass or less, still more preferably 95% by mass or more, in the resin composition. It is more than mass % and below 99 mass %.
• the glass transition temperature (Tg) of the cyclic olefin polymer (A) according to this embodiment is preferably in the range of 130°C or higher and 170°C or lower.
• Tg glass transition temperature of the cyclic olefin-based polymer (A)
• sufficient heat resistance is obtained when used as an optical component requiring heat resistance, such as a vehicle-mounted camera lens or a camera lens for mobile devices. can be obtained, and good moldability can be obtained.
• the glass transition temperature (Tg) of the cyclic olefin polymer (A) according to this embodiment can be measured using a differential scanning calorimeter (DSC).
• DSC differential scanning calorimeter
• the temperature was raised from room temperature to 200 ° C. at a temperature increase rate of 10 ° C./min in a nitrogen atmosphere, held for 5 minutes, and then cooled at a temperature decrease rate of 10 ° C./min. C., hold for 5 minutes, and then raise the temperature to 200.degree. C. at a heating rate of 10.degree.
• the dye (B) used in the present embodiment may be composed of one or more dyes, and at least one dye is preferably a squarylium dye represented by the following general formula (1). .
• R 1 to R 10 each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 1 to 20 carbon atoms, or 1 to 10 carbon atoms.
• halogenoalkyl groups alkoxy groups having 1 to 20 carbon atoms, halogenoalkoxy groups having 1 to 20 carbon atoms, alkylthio groups having 1 to 20 carbon atoms, alkoxyalkyl groups having 1 to 20 carbon atoms, alkoxyalkyl groups having 1 to 20 carbon atoms, alkoxyalkoxyalkyl group, halogenoalkoxyalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted aryl group, substituted or unsubstituted aralkyl group, substituted or unsubstituted amino group, substituted or unsubstituted acyl group, substituted or unsubstituted An unsubstituted aryloxy group, a substituted or unsubstituted aryloxyalkyl group, a substituted or unsubstituted aralkyloxy group, a substituted or unsubstituted aralkyloxyalkyl
• substituents when the above groups have substituents include a phenyl group, a tolyl group, a benzyl group, a phenethyl group, a benzoyl group, a formyl group, and an acetyl group.
• R 1 to R 10 are preferably a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 1 to 20 carbon atoms, and more preferably an alkyl group having 1 to 20 carbon atoms.
• R 4 and R 9 are preferably alkyl groups having 3 or more carbon atoms.
• the upper limit of the number of carbon atoms is not particularly limited, it is 20 or less. This improves the compatibility between the squarylium-based dye and the cyclic olefin-based polymer (A), and further improves the heat resistance of the resulting molded product.
• the squarylium-based dye having the above structure has a steep absorption peak near 700 nm, less absorption in other wavelength bands, and high heat resistance and light resistance, and is suitable for the present embodiment.
• squarylium dye having the above structure examples include 1,3-bis[6-[(2-ethyl-1-oxohexyl)amino]-2,3-dihydro-2,3,3-trimethyl-1- Octyl-1H-indol-5-yl]-2,4-dihydroxy-cyclobutenediilium, 1,3-bis[6-[(2-ethyl-1-oxohexyl)amino]-2,3-dihydro- 2,3,3-trimethyl-1-(propan-2-yl)-1H-indol-5-yl]-2,4-dihydroxy-cyclobutenedilium and the like.
• the other dye include anthraquinone-based dye, benzotriazole-based dye, benzophenone-based dye, triazine-based dye, cyclic iminoester-based dye, and indole-based dye.
• Benzotriazole dyes are particularly preferred from the viewpoint of heat resistance and light resistance.
• benzotriazole dyes include 2-(2-hydroxy-5-methylphenyl)benzotriazole, 2-(2-hydroxy-5-tert-octylphenyl)benzotriazole, 2-(2-hydroxy -3,5-dicumylphenyl)phenylbenzotriazole, 2-(2-hydroxy-3-tert-butyl-5-methylphenyl)-5-chlorobenzotriazole, 2,2′-methylenebis[4-(1, 1,3,3-tetramethylbutyl)-6-(2N-benzotriazol-2-yl)phenol], 2-(2-hydroxy-3,5-di-tert-butylphenyl)benzotriazole, 2- (2-hydroxy-3,5-di-tert-butylphenyl)-5-chlorobenzotriazole, 2-(2-hydroxy-3,5-di-tert-amylphenyl)benzotriazole, 2-(2- hydroxy-5-tert-octylphenyl)
• Benzotriazole dyes which are other dyes used in combination, include 2-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-5-(ethyl amino)-4-methylphenol, 2-(2'-hydroxy-3'-t-butyl-5'-methylphenyl)-5-octylsulfanylbenzotriazole, (2-(2-hydroxy-5-tert-butyl phenyl)benzotriazole, 2-(2-hydroxy-4-n-octyloxyphenyl)benzotriazole, 2,2'-methylenebis(4-cumyl-6-benzotriazolephenyl), 2,2'-p- Phenylenebis(1,3-benzoxazin-4-one), 2-[2-hydroxy-3-(3,4,5,6-tetrahydrophthalimidomethyl)-5-methylphenyl]benzotriazole) are preferred, 2-(5-chloro-2H-benzo[d][1,2,3
• the total content of dyes in the resin composition is preferably 100 ppm or more and 5000 ppm or less, more preferably 100 ppm or more and 3000 ppm or less, relative to the resin composition for forming an optical component. It is particularly preferred to have By setting the amount of the pigment within the above numerical range, the resin composition can provide a molded product with less color unevenness and uniform color.
• the content of the squarylium-based dye in the resin composition is 10 ppm or more and 2000 ppm or less with respect to the resin composition for forming an optical component, from the viewpoint of the effects of the present invention. is preferred, and 10 ppm or more and 500 ppm or less is particularly preferred.
• the content of the squarylium dye is preferably 0.001 parts by mass or more and 0.2 parts by mass or less, and preferably 0.001 parts by mass with respect to 100 parts by mass of the cyclic olefin polymer. Parts or more and 0.05 parts by mass or less are more preferable.
• the content of the squarylium-based dye is preferably 2% by mass or more and 100% by mass or less, more preferably 3% by mass or more and 50% by mass or less, relative to the total content of the dyes of 100% by mass.
• the resin composition for forming an optical component according to the present embodiment may optionally include known additives as optional components within a range that does not impair the resin composition according to the present embodiment and the molded article thereof. can be contained.
• Additives include, for example, phenol stabilizers, higher fatty acid metal salts, antioxidants, ultraviolet absorbers, hindered amine light stabilizers, hydrochloric acid absorbers, metal deactivators, antistatic agents, antifog agents, and lubricants. , a slip agent, a nucleating agent, a plasticizer, a flame retardant, a phosphorus-based stabilizer, etc., can be blended to such an extent that the objects of the present invention are not impaired, and the blending ratio is an appropriate amount.
• the total content of the cyclic olefin polymer and the dye in the resin composition for forming an optical component according to the embodiment is preferably 50% by mass when the entire resin composition for forming an optical component is taken as 100% by mass. 100% by mass or less, more preferably 60% by mass or more and 100% by mass or less, still more preferably 70% by mass or more and 100% by mass or less, and particularly preferably 80% by mass or more and 100% by mass or less.
• the resin composition for forming an optical component according to the embodiment is prepared by melt-kneading a cyclic olefin polymer and a raw material containing a dye using a known kneading device such as an extruder and a Banbury mixer; and a method of dissolving a raw material containing a dye in a common solvent and then evaporating the solvent; a method of adding a cyclic olefin polymer and a raw material solution containing a dye into a poor solvent to precipitate; can be done.
• the resin composition for forming an optical component according to the present embodiment contains a cyclic olefin polymer (A) and a squarylium dye (B),
• Cyclic olefin polymer (A) is selected from cyclic olefin copolymer (A-1) of ethylene or ⁇ -olefin and cyclic olefin, and ring-opening polymer of cyclic olefin (A-2) including at least one
• At least one of the squarylium dyes (B) is preferably a squarylium dye represented by the general formula (1).
• the resin composition for forming an optical component according to the present embodiment has a thickness such that the transmittance of light having a wavelength of 700 nm is 30% in a molded body made of the resin composition for forming an optical component, and the following (1) All the conditions of (3) are satisfied.
• the average transmittance at a wavelength of 300 to 400 nm is 40% or less, preferably 30% or less, more preferably 20% or less.
• the average transmittance at a wavelength of 500 to 600 nm is 70% or more, preferably 80% or more, more preferably 85% or more.
• the transmittance at a wavelength of 650 nm is 60% or more, preferably 65% or more, and more preferably 70% or more.
• the resin composition for forming an optical component according to the present embodiment adjusts the transmission characteristics (1) to (3) within the above numerical range in the case of a molded body having a thickness such that the transmittance of light with a wavelength of 700 nm is 30%. By doing so, it is possible to provide a resin composition that, when used as a lens, improves color bleeding while suppressing unnecessary image coloring.
• the transmittance at each wavelength of the resin composition for forming an optical component according to this embodiment can be obtained as follows. First, for example, by press molding (260° C., 10 minutes, pressure 10 MPa), a rectangular plate made of the resin composition for forming an optical component according to this embodiment is obtained. Using the obtained plate as a sample, an ultraviolet-visible-near-infrared spectrophotometer (for example, an ultraviolet-visible-near-infrared spectrophotometer U-4150 (manufactured by Hitachi High-Tech)) is used to measure the transmittance in increments of 1 nm from a wavelength of 200 nm to 1000 nm. to measure.
• an ultraviolet-visible-near-infrared spectrophotometer for example, an ultraviolet-visible-near-infrared spectrophotometer U-4150 (manufactured by Hitachi High-Tech)
• a sample having a thickness such that the transmittance of light with a wavelength of 700 nm becomes 30% is employed, and the above transmittances (1) to (3) are measured.
• the average value of the transmittance at wavelengths of 300 to 400 nm indicates the arithmetic average value of the transmittances measured at intervals of 1 nm from 300 nm to 400 nm.
• the optical component-forming resin composition according to the present embodiment satisfies all of the following conditions (1) to (5) in a 1 mm-thick molded body made of the optical component-forming resin composition.
• the average transmittance at a wavelength of 300 to 400 nm is 40% or less, preferably 30% or less, more preferably 20% or less.
• the average transmittance at a wavelength of 500 to 600 nm is 70% or more, preferably 80% or more, more preferably 85% or more.
• the transmittance at a wavelength of 650 nm is 60% or more, preferably 65% or more, and more preferably 70% or more.
• the minimum transmittance at a wavelength of 660 nm to 750 nm is 30% or less, preferably 25% or less, more preferably 20% or less.
• the internal haze is 1.0% or less, preferably 0.7% or less, more preferably 0.4% or less.
• the resin composition for forming an optical component according to the present embodiment can be used as a lens by adjusting the transmission characteristics (1) to (5) within the above numerical range in the case of a molded body having a thickness of 1 mm. It is possible to provide a resin composition that suppresses coloration of unnecessary images and improves color bleeding.
• the transmittance at each wavelength of the resin composition for forming an optical component according to this embodiment can be obtained as follows. First, for example, by press molding (260° C., 10 minutes, pressure 10 MPa), a rectangular plate having a thickness of 1 mm and made of the resin composition for forming an optical component according to the present embodiment is obtained. Using the obtained 1 mm thick plate as a sample, an ultraviolet-visible near-infrared spectrophotometer (for example, an ultraviolet-visible near-infrared spectrophotometer U-4150 (manufactured by Hitachi High-Tech)) is used to measure wavelengths from 200 nm to 1000 nm in increments of 1 nm.
• an ultraviolet-visible near-infrared spectrophotometer for example, an ultraviolet-visible near-infrared spectrophotometer U-4150 (manufactured by Hitachi High-Tech)
• the average value of the transmittance at wavelengths of 300 to 400 nm indicates the arithmetic average value of the transmittances measured at intervals of 1 nm from 300 nm to 400 nm.
• a 1 mm-thick molded body made of the optical component-forming resin composition has a refractive index of 1.50 or more at a wavelength of 587 nm at a measurement temperature of 25°C. is preferred, 1.52 or more is more preferred, and 1.54 or more is even more preferred.
• the thickness of the lens can be made thinner than that of a resin composition outside the above numerical range, for example, when used as a lens. can.
• the refractive index of a molded article made of the optical component-forming resin composition can be obtained by the following method. First, a plate having a thickness of 1 mm made of the resin composition for forming an optical component according to the present embodiment is obtained by press molding, for example. Using the obtained plate as a sample, the refractive index at a wavelength of 587 nm is measured at a measurement temperature of 25° C. using a refractometer (for example, refractometer KPR-3000 (manufactured by Shimadzu Corporation)).
• a refractometer for example, refractometer KPR-3000 (manufactured by Shimadzu Corporation)
• the molded article according to this embodiment is a molded article obtained by molding the resin composition for forming an optical component according to this embodiment.
• the molded article according to the present embodiment is a molded article made of a resin composition for forming an optical part containing the cyclic olefin polymer (A) and the dye (B).
• the molded article according to the present embodiment sufficiently suppresses the occurrence of color fringing such as purple fringing, and maintains the light transmittance that can be used as an optical member for imaging and the light absorption at a specific wavelength. Since sufficient light transmittance can be maintained even at , it can be suitably used as an optical component. That is, the optical component according to this embodiment includes the molded body according to this embodiment. The optical component according to this embodiment can be suitably used as an optical component such as a lens, for example. Examples of optical products including the optical component (lens) include smartphones, tablets, digital cameras, and the like.
• the molded article according to this embodiment can be obtained by molding the resin composition for forming an optical component according to this embodiment into a predetermined shape.
• the method for obtaining a molded product by molding the resin composition for forming an optical component according to the present embodiment is not particularly limited, and a known method can be used.
• the composition is preferably shaped by melt molding.
• extrusion molding, injection molding, compression molding, inflation molding, blow molding, extrusion blow molding, injection blow molding, press molding, vacuum molding, powder slush molding, calendar molding, foam molding, etc. is applicable.
• the injection molding method is preferable from the viewpoint of moldability and productivity. Molding conditions are appropriately selected depending on the purpose of use or the molding method.
• the resin temperature in injection molding is usually 150°C to 400°C, preferably 200°C to 350°C, more preferably 230°C to 330°C. It is selected appropriately within the range.
• the molded article according to the present embodiment can be used in various forms such as lens-shaped, spherical, rod-shaped, plate-shaped, columnar, cylindrical, tube-shaped, fibrous, film- or sheet-shaped.
• Resin 1 Copolymer of ethylene and cyclic olefin (tetracyclo[4.4.0.12,5.17,10]-3-dodecene) (manufactured by Mitsui Chemicals, product name: APEL 5014CL: MFR: 36 g/ 10 min (260°C, 2.16 kg load, conforming to ASTM D1238), Tg: 135°C)
• Resin 2 Copolymer of ethylene and cyclic olefin (tetracyclo[4.4.0.12,5.17,10]-3-dodecene) (manufactured by Mitsui Chemicals, product name: APEL 5514ML: MFR: 36 g/ 10 min (260°C, 2.16 kg load, conforming to ASTM D1238), Tg: 135°C)
• Resin 3 Ring-opening polymer of cyclic olefin (manufactured by JSR, product name: ARTON F4520: M
• Squarylium dye 1 1,3-bis[6-[(2-ethyl-1-oxohexyl)amino]-2,3-dihydro-2,3,3-trimethyl-1-octyl-1H-indole-5 -yl]-2,4-dihydroxy-cyclobutenediilium
• Squarylium dye 2 1,3-bis[6-[(2-ethyl-1-oxohexyl)amino]-2,3-dihydro-2,3,3-trimethyl-1-(propan-2-yl) -1H-indol-5-yl]-2,4-dihydroxy-cyclobutenediilium
• Benzotriazole dye 1 2-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-5-(ethylamino)-4-methylphenol
• Benzotriazole dye 2 2-(2'-hydroxy-3'-t-butyl-5'-methylphenyl)-5-octylsulfanyl benzotriazole
• Indole dye 1 ethyl 2-cyano-3-(1-methyl-2-phenyl-1H-indol-3-yl) acrylate
• Anthraquinone dye 1 1-methylamino-4-[(3-methylphenyl)amino]-9,10-anthraquinone
• Example 1 60 ppm of squarylium-based dye 1, 240 ppm of benzotriazole-based dye 1, and 1000 ppm of benzotriazole-based dye 2 were added to pellets made of resin 1, and the mixture was mixed at 260°C using a batch-type melt-kneading apparatus (Laboplastomill). A resin composition was obtained by melt-kneading. The obtained resin composition was press-molded at 260° C. for 10 minutes at a pressure of 10 MPa to prepare a 1 mm-thick plate and a 0.4 mm-thick plate having a transmittance of 30% for light with a wavelength of 700 nm.
• Example 2 25 ppm of squarylium-based dye 1, 240 ppm of benzotriazole-based dye 1, and 1000 ppm of benzotriazole-based dye 2 were added to the pellets made of Resin 1, and the mixture was obtained at 260°C using a batch-type melt-kneading apparatus (Laboplastomill). A resin composition was obtained by melt-kneading. The obtained resin composition was press-molded at 260° C. for 10 minutes under a pressure of 10 MPa to prepare a plate having a thickness of 1 mm.
• Example 3 50 ppm of squarylium-based dye 2, 240 ppm of benzotriazole-based dye 1, and 1000 ppm of benzotriazole-based dye 2 were added to the pellets made of resin 1, and mixed at 260°C using a batch-type melt-kneading apparatus (Laboplastomill). A resin composition was obtained by melt-kneading. The obtained resin composition was press-molded at 260° C. for 10 minutes under a pressure of 10 MPa to prepare a 1 mm-thick plate and a 0.3 mm-thick plate having a transmittance of 30% for light with a wavelength of 700 nm.
• Example 4 20 ppm of squarylium-based dye 2, 240 ppm of benzotriazole-based dye 1, and 1000 ppm of benzotriazole-based dye 2 were added to pellets made of resin 1, and the mixture was mixed at 260°C using a batch-type melt-kneading apparatus (Laboplastomill). A resin composition was obtained by melt-kneading. The obtained resin composition was press-molded at 260° C. for 10 minutes under a pressure of 10 MPa to prepare a plate having a thickness of 1 mm.
• Example 5 60 ppm of squarylium-based dye 1 and 2000 ppm of benzotriazole-based dye 2 are added to pellets made of Resin 1, and melt-kneaded at 260° C. using a batch-type melt-kneading apparatus (Laboplastomill) to obtain a resin composition. rice field. The obtained resin composition was press-molded at 260° C. to prepare a 1 mm-thick plate and a 0.4 mm-thick plate having a transmittance of 30% for light with a wavelength of 700 nm.
• Example 6 25 ppm of squarylium-based dye 1 and 2000 ppm of benzotriazole-based dye 2 are added to pellets made of Resin 1, and melt-kneaded at 260° C. using a batch-type melt-kneading apparatus (Laboplastomill) to obtain a resin composition. rice field. The obtained resin composition was press-molded at 260° C. to produce a plate having a thickness of 1 mm.
• Example 7 20 ppm of squarylium-based dye 2 and 2000 ppm of benzotriazole-based dye 2 are added to pellets made of resin 1, and melt-kneaded at 260° C. using a batch-type melt-kneading apparatus (Laboplastomill) to obtain a resin composition. rice field. The obtained resin composition was press-molded at 260° C. to produce a plate having a thickness of 1 mm.
• Example 8 60 ppm of squarylium-based dye 1 and 1000 ppm of indole-based dye 1 were added to pellets made of Resin 1, and melt-kneaded at 260° C. using a batch-type melt-kneading apparatus (Laboplastomill) to obtain a resin composition. .
• the obtained resin composition was press-molded at 260° C. to prepare a 1 mm-thick plate and a 0.4 mm-thick plate having a transmittance of 30% for light with a wavelength of 700 nm.
• Example 9 60 ppm of squarylium-based dye 1, 240 ppm of benzotriazole-based dye 1, and 1000 ppm of benzotriazole-based dye 2 were added to the pellets made of resin 2, and mixed at 260° C. using a batch-type melt-kneading apparatus (Laboplastomill). A resin composition was obtained by melt-kneading. The obtained resin composition was press-molded at 260° C. for 10 minutes at a pressure of 10 MPa to prepare a 1 mm-thick plate and a 0.4 mm-thick plate having a transmittance of 30% for light with a wavelength of 700 nm.
• Example 10 50 ppm of squarylium-based dye 2, 240 ppm of benzotriazole-based dye 1, and 1000 ppm of benzotriazole-based dye 2 were added to the pellets made of resin 2, and mixed at 260°C using a batch-type melt-kneading apparatus (Laboplastomill). A resin composition was obtained by melt-kneading. The obtained resin composition was press-molded at 260° C. for 10 minutes under a pressure of 10 MPa to prepare a 1 mm-thick plate and a 0.3 mm-thick plate having a transmittance of 30% for light with a wavelength of 700 nm.
• Example 11 60 ppm of squarylium-based dye 1 and 2000 ppm of benzotriazole-based dye 2 are added to the pellets made of Resin 2, and melt-kneaded at 260° C. using a batch-type melt-kneading apparatus (Laboplastomill) to obtain a resin composition. rice field. The obtained resin composition was press-molded at 260° C. for 10 minutes at a pressure of 10 MPa to prepare a 1 mm-thick plate and a 0.4 mm-thick plate having a transmittance of 30% for light with a wavelength of 700 nm.
• Example 12 60 ppm of squarylium dye 1 and 1000 ppm of indole dye 1 were added to pellets made of Resin 2, and melt-kneaded at 260° C. using a batch-type melt-kneader (Laboplastomill) to obtain a resin composition. .
• the obtained resin composition was press-molded at 260° C. to prepare a 1 mm-thick plate and a 0.4 mm-thick plate having a transmittance of 30% for light with a wavelength of 700 nm.
• Example 13 60 ppm of squarylium-based dye 1, 240 ppm of benzotriazole-based dye 1, and 1000 ppm of benzotriazole-based dye 2 were added to the pellets made of Resin 3, and mixed at 260° C. using a batch-type melt-kneading apparatus (Laboplastomill). A resin composition was obtained by melt-kneading. The obtained resin composition was press-molded at 260° C. for 10 minutes at a pressure of 10 MPa to prepare a 1 mm-thick plate and a 0.4 mm-thick plate having a transmittance of 30% for light with a wavelength of 700 nm.
• Example 14 60 ppm of squarylium-based dye 1, 240 ppm of benzotriazole-based dye 1, and 1000 ppm of benzotriazole-based dye 2 were added to the pellets made of resin 4, and mixed at 260° C. using a batch-type melt-kneading apparatus (Laboplastomill). A resin composition was obtained by melt-kneading. The obtained resin composition was press-molded at 260° C. for 10 minutes at a pressure of 10 MPa to prepare a 1 mm-thick plate and a 0.4 mm-thick plate having a transmittance of 30% for light with a wavelength of 700 nm.
• the resin compositions obtained in Examples 1 to 14 and Comparative Examples 1 and 2 were evaluated as follows. [Evaluation of transmittance] Using the obtained plate as a sample, the transmittance was measured in increments of 1 nm from a wavelength of 200 nm to 1000 nm using an ultraviolet-visible-near-infrared spectrophotometer U-4150 (manufactured by Hitachi High-Tech). Average transmittance at a wavelength of 500 to 600 nm, transmittance at a wavelength of 650 nm, and minimum transmittance at a wavelength of 660 to 750 nm were calculated.
• PF purple fringe
• the color of the PF generated portion and the non-generated portion of the edge of the subject was respectively expressed in the Lab color system, and the distance between the two in the Lab color space was used as an index of color fringing (amount of color fringing), and evaluated according to the following criteria. . 10 or less: ⁇ More than 10 and less than 15: ⁇ 15 or more: ⁇
• the color of the PF non-occurring part and the color of the same part when photographed without sticking the plate together is expressed in the Lab color system, and the distance between the two in the Lab color space is the index (coloring amount) of the image. and evaluated according to the following criteria. 10 or less: ⁇ More than 10 and less than 15: ⁇ 15 or more: ⁇
• the occurrence of color bleeding such as purple fringing is sufficiently suppressed.
• the amount of change in transmittance and the amount of change in minimum transmittance at a wavelength of 660 to 750 nm were calculated and evaluated according to the following criteria. -1% or more and 1% or less: ⁇ -2% or more and less than -1%, more than 1% and 2% or less: ⁇ Less than -2%, more than 2%: ⁇
• the light transmittance of the plate after the test was measured by the above method, and the amount of change in the average transmittance at a wavelength of 300 to 400 nm when compared with that before the test, the amount of change in the average transmittance at a wavelength of 500 to 600 nm, and the amount of change in the average transmittance at a wavelength of 650 nm.
• the amount of change in transmittance and the amount of change in minimum transmittance at a wavelength of 660 to 750 nm were calculated and evaluated according to the following criteria. -1% or more and 1% or less: ⁇ -2% or more and less than -1%, more than 1% and 2% or less: ⁇ Less than -2%, more than 2%: ⁇

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