WO2025070288A1 - 樹脂組成物、成形体および光学部品 - Google Patents

樹脂組成物、成形体および光学部品 Download PDF

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Publication number
WO2025070288A1
WO2025070288A1 PCT/JP2024/033632 JP2024033632W WO2025070288A1 WO 2025070288 A1 WO2025070288 A1 WO 2025070288A1 JP 2024033632 W JP2024033632 W JP 2024033632W WO 2025070288 A1 WO2025070288 A1 WO 2025070288A1
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Prior art keywords
resin composition
mass
fatty acid
pentaerythritol
acid ester
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PCT/JP2024/033632
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English (en)
French (fr)
Japanese (ja)
Inventor
昌克 春谷
太 藤村
大樹 冷水
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Mitsui Chemicals Inc
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Mitsui Chemicals Inc
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Priority to CN202480033604.8A priority Critical patent/CN121152836A/zh
Priority to JP2025515404A priority patent/JPWO2025070288A1/ja
Priority to KR1020257013569A priority patent/KR20250075675A/ko
Publication of WO2025070288A1 publication Critical patent/WO2025070288A1/ja
Priority to JP2025139460A priority patent/JP2025172809A/ja
Anticipated expiration legal-status Critical
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    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/04Oxygen-containing compounds
    • C08K5/10Esters; Ether-esters
    • C08K5/101Esters; Ether-esters of monocarboxylic acids
    • C08K5/103Esters; Ether-esters of monocarboxylic acids with polyalcohols
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F232/00Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/04Oxygen-containing compounds
    • C08K5/05Alcohols; Metal alcoholates
    • C08K5/053Polyhydroxylic alcohols
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/04Oxygen-containing compounds
    • C08K5/09Carboxylic acids; Metal salts thereof; Anhydrides thereof
    • C08K5/098Metal salts of carboxylic acids
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/16Nitrogen-containing compounds
    • C08K5/17Amines; Quaternary ammonium compounds
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L45/00Compositions of homopolymers or copolymers of compounds having no unsaturated aliphatic radicals in side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic or in a heterocyclic ring system; Compositions of derivatives of such polymers
    • GPHYSICS
    • G02OPTICS
    • G02BOPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04Optical 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 a resin composition, a molded body, and an optical component.
  • Cyclic olefin copolymer resin compositions have excellent optical properties and are therefore used, for example, as optical components such as optical lenses.
  • Patent Document 1 discloses a resin composition comprising a thermoplastic norbornene resin and (a) a compound represented by the general formula: RX n (wherein n is a natural number, R is a hydrocarbon group which may have a hydroxyl group, and X is a hydroxyacyloxy group, provided that when n is 2 or more, the n Xs may or may not be the same, and the total number of carbon atoms in the formula is 16 or more) and/or (b) a saturated alcohol having 16 or more carbon atoms, for the purpose of obtaining a thermoplastic norbornene resin composition which exhibits sufficient mold releasability in melt molding or the like, does not generate voids, and has the heat resistance, chemical resistance, electrical properties, and the like of thermoplastic norbornene resins.
  • RX n wherein n is a natural number, R is a hydrocarbon group which may have a hydroxyl group, and X is a hydroxyacyloxy group, provided that when
  • the present invention has been made in consideration of the above circumstances, and provides a resin composition capable of obtaining molded articles and optical components having an improved performance balance between moist heat resistance and transparency, and a molded article and optical component having an improved performance balance between moist heat resistance and transparency.
  • the present inventors conducted extensive research to achieve the above object. As a result, they discovered that by using a fatty acid ester composition having a pentaerythritol content within a specific range, it is possible to provide a resin composition capable of producing molded articles and optical components having an improved performance balance between moist heat resistance and transparency, as well as molded articles and optical components having an improved performance balance between moist heat resistance and transparency, and thus arrived at the present invention.
  • the present invention provides the following resin composition, molded body, and optical component.
  • a resin composition comprising:
  • the cyclic olefin copolymer (A) is At least one olefin-derived repeating unit (a) represented by the following general formula (I); and at least one repeating unit (b) derived from a cyclic olefin monomer selected from the group consisting of a repeating unit (AA) represented by the following general formula (II), a repeating unit (AB) represented by the following general formula (III), and a repeating unit (AC) represented by the following general formula (IV),
  • a resin composition wherein the content of the pentaerythritol (B-1) in the fatty acid ester composition (B) is 5.0 mass% or less, when the total content of the pentaery
  • R 300 represents a hydrogen atom or a linear or branched hydrocarbon group having 1 to 29 carbon atoms.
  • u is 0 or 1
  • v is 0 or a positive integer
  • w is 0 or 1
  • R 61 to R 78 as well as R a1 and R b1 may be the same or different and are each 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, 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 be bonded to each other to form a monocycle or polycycle.
  • x and d are 0 or an integer of 1 or more
  • y and z are 0, 1 or 2
  • R 81 to R 99 may be the same or different and are
  • the pentaerythritol fatty acid ester (B-2) is a resin composition containing a compound represented by the following formula (1).
  • R is a saturated hydrocarbon group having 11 to 17 carbon atoms.
  • the resin composition further comprises a fatty acid metal salt (C).
  • the resin composition further comprises a hindered amine compound (D).
  • the resin composition has a content of the hindered amine compound (D) of 0.05 parts by mass or more and 3.0 parts by mass or less based on 100 parts by mass of the cyclic olefin copolymer (A).
  • the cyclic olefin copolymer (A) is a random copolymer of ethylene and tetracyclo[4.4.0.1 2,5 .
  • a test piece having an optical surface of 35 mm ⁇ 65 mm ⁇ thickness of 10 mm.
  • the internal haze of the injection molded test piece is measured using benzyl alcohol with a haze meter based on JIS K7136:2000.
  • a molded article comprising the resin composition according to any one of [1] to [19] above.
  • An optical component comprising the molded article according to [20] above.
  • the present invention can provide a resin composition that can produce molded articles and optical components with an improved balance of moist heat resistance and transparency, as well as molded articles and optical components with an improved balance of moist heat resistance and transparency.
  • the resin composition of the present embodiment is a resin composition comprising a cyclic olefin copolymer (A) and a fatty acid ester composition (B) comprising pentaerythritol (B-1) and a fatty acid ester of pentaerythritol (B-2), wherein the cyclic olefin copolymer (A) comprises at least one olefin-derived repeating unit (a) represented by the following general formula (I), and at least one cyclic olefin monomer-derived repeating unit (b) selected from the group consisting of repeating units (AA) represented by the following general formula (II), repeating units (AB) represented by the following general formula (III), and repeating units (AC) represented by the following general formula (IV), and the content of the pentaerythritol (B-1) in the fatty acid ester composition (B) is 5.0 mass%
  • R 300 represents a hydrogen atom or a linear or branched hydrocarbon group having 1 to 29 carbon atoms.
  • u is 0 or 1
  • v is 0 or a positive integer, preferably an integer of 0 to 2, more preferably 0 or 1
  • w is 0 or 1
  • R 61 to R 78 as well as R a1 and R b1 may be the same or different and are 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, 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 be bonded to each other to form a monocycle or polycycle.
  • R 100 and R 101 may be the same or different and each represent a hydrogen atom or a hydrocarbon group having 1 to 5 carbon atoms, and f is 1 ⁇ f ⁇ 18.
  • the resin composition of the present embodiment it is possible to obtain a molded article and an optical component having an improved balance of performance between moist heat resistance and transparency.
  • the reason for this is unclear, but it is believed that when the content of pentaerythritol in the fatty acid ester composition (B) is within a specific range, pentaerythritol, which has a higher polarity, is uniformly dispersed in the cyclic olefin copolymer (A), which has a lower polarity, without phase separation, thereby improving the performance balance of the moist heat resistance and transparency of the obtained molded body and optical component.
  • the resin composition of this embodiment can provide thick molded articles and optical components with an improved balance of moist heat resistance and transparency, even when such articles and optical components are produced.
  • the content of pentaerythritol (B-1) in the fatty acid ester composition (B) is 5.0% by mass or less, preferably 4.5% by mass or less, more preferably 3.0% by mass or less, even more preferably 2.5% by mass or less, even more preferably 2.0% by mass or less, even more preferably 1.8% by mass or less, even more preferably 1.5% by mass or less, even more preferably 1.0% by mass or less, even more preferably 0.8% by mass or less, even more preferably 0.5% by mass or less, when the total content of pentaerythritol (B-1) and the fatty acid ester of pentaerythritol (B-2) in the fatty acid ester composition (B) is taken as 100% by mass.
  • the content of pentaerythritol (B-1) the above upper limit or less, the performance balance of the moist heat resistance and transparency of the molded body and optical parts using the resin composition of this embodiment can be improved.
  • the lower limit of the content of pentaerythritol (B-1) in the fatty acid ester composition (B) is not particularly limited, and may be, for example, 0.01 mass% or more, optionally 0.05 mass% or more, optionally 0.1 mass% or more, optionally 0.3 mass% or more, or optionally 0.4 mass% or more.
  • the content of pentaerythritol (B-1) in the fatty acid ester composition (B) of the present embodiment is preferably from 0.01% by mass to 5.0% by mass, more preferably from 0.01% by mass to 4.0% by mass, based on the total content of pentaerythritol (B-1) and the fatty acid ester of pentaerythritol (B-2) in the fatty acid ester composition (B) being 100% by mass.
  • the content of pentaerythritol (B-1) in the fatty acid ester composition (B) can be determined by preparing a calibration curve using, for example, pentaerythritol (manufactured by Wako Pure Chemical Industries, Ltd.) and then quantitatively measuring the content by gas chromatography.
  • the measurement conditions can be exemplified as follows: Measurement equipment: 6890N (Agilent Technologies) Column: DB-1HT (manufactured by J&W) Carrier gas: He (constant flow mode) Detector: FID More specifically, the content of pentaerythritol (B-1) in the fatty acid ester composition (B) of the present embodiment can be measured by the method described in paragraphs 0168 to 0170 of Japanese Patent No. 5778884.
  • the cyclic olefin copolymer (A) in the resin composition of the present embodiment contains at least one olefin-derived repeating unit (a) represented by the above general formula (I) and at least one cyclic olefin monomer-derived repeating unit (b) selected from the group consisting of repeating units (AA) represented by the above general formula (II), repeating units (AB) represented by the above general formula (III), and repeating units (AC) represented by the above general formula (IV).
  • the olefin monomer which is one of the copolymerization raw materials for the cyclic olefin copolymer (A) of this embodiment, undergoes addition copolymerization to form the repeating unit (a) represented by the above general formula (I). Specifically, an olefin monomer represented by the following general formula (Ia) that corresponds 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.
  • the olefin monomer represented by the above 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.
  • the olefin monomer represented by the general formula (Ia) is preferably at least one selected from ethylene and propylene, more preferably ethylene, from the viewpoint of obtaining a molded article having better heat resistance, mechanical properties, and optical properties. That is, the repeating unit (a) in the cyclic olefin copolymer (A) preferably contains a repeating unit derived from at least one selected from ethylene and propylene, more preferably contains a repeating unit derived from ethylene. Two or more types of olefin monomers represented by the general formula (Ia) may be used. In addition, the olefin monomer may contain at least one biomass-derived monomer (ethylene, propylene, ⁇ -olefin).
  • the proportion of repeating units (a) in the cyclic olefin copolymer (A) of this embodiment is preferably 5 mol % or more, more preferably 20 mol % or more, even more preferably 40 mol % or more, even more preferably 50 mol % or more, and even more preferably 60 mol % or more.
  • the proportion of olefin-derived repeating units (a) in the cyclic olefin copolymer (A) of this embodiment is preferably 95 mol% or less, more preferably 90 mol% or less, even more preferably 85 mol% or less, even more preferably 80 mol% or less, even more preferably 75 mol% or less, even more preferably 70 mol% or less, and even more preferably 65 mol% or less.
  • the proportion of the repeating unit (a) derived from an olefin in the cyclic olefin copolymer (A) of this embodiment is preferably 5 mol% or more and 95 mol% or less, more preferably 5 mol% or more and 90 mol% or less, even more preferably 5 mol% or more and 85 mol% or less, even more preferably 20 mol% or more and 80 mol% or less, even more preferably 40 mol% or more and 75 mol% or less, even more preferably 50 mol% or more and 70 mol% or less, and even more preferably 60 mol% or more and 65 mol% or less.
  • the proportion of the repeating unit (a) derived from an olefin can be measured by 13 C-NMR.
  • the cyclic olefin monomer which is one of the copolymerization raw materials for the cyclic olefin copolymer (A) of this embodiment, undergoes addition copolymerization to form repeating units (b) derived from the cyclic olefin monomer represented by the above general formula (II), (III), or (IV).
  • repeating units (b) derived from the cyclic olefin monomer represented by the above general formula (II), (III), or (IV).
  • cyclic olefin monomers represented by general formulas (IIa), (IIIa), and (IVa), which correspond to the above general formulas (II), (III), and (IV), respectively, are used.
  • u is 0 or 1
  • v is 0 or a positive integer, preferably an integer of 0 to 2, more preferably 0 or 1
  • w is 0 or 1
  • R 61 to R 78 as well as R a1 and R b1 may be the same or different and are 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, 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 be bonded to each other to form a monocycle or polycycle.
  • 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, and f is 1 ⁇ f ⁇ 18.
  • the solubility of the cyclic olefin copolymer (A) in the solvent is further improved, resulting in good moldability and improved product yield.
  • cyclic olefin monomers represented by general formula (IIa), (IIIa) or (IVa) include the compounds described in paragraphs 0037 to 0063 of WO 2006/118261.
  • the cyclic olefin monomers are obtained from dicyclopentadiene and ethylene, and the ethylene may contain units derived from a biomass-derived monomer (ethylene).
  • bicyclo-2-heptene derivatives bicyclohept-2-ene derivatives
  • tricyclo-3-decene derivatives tricyclo-3-undecene derivatives
  • tetracyclo-3-dodecene derivatives pentacyclo-4-pentadecene derivatives, pentacyclopentadecadiene derivatives, pentacyclo-3-pentadecene derivatives, pentacyclo-4-hexadecene derivatives, pentacyclo-3-hexadecene derivatives, hexacyclo-4-heptadecene derivatives, and heptacyclo-5-eicosene.
  • heptacyclo-4-eicosene derivatives heptacyclo-5-heneicosene derivatives, octacyclo-5-docosene derivatives, nonacyclo-5-pentacosene derivatives, nonacyclo-6-hexacosene derivatives, cyclopentadiene-acenaphthylene adducts, 1,4-methano-1,4,4a,9a-tetrahydrofluorene derivatives, 1,4-methano-1,4,4a,5,10,10a-hexahydroanthracene derivatives, cycloalkylene derivatives having 3 to 20 carbon atoms, etc.
  • a repeating unit derived from a cyclic olefin monomer represented by general formula (IIa), among the cyclic olefin monomers represented by general formula (IIa), (IIIa) or (IVa), i.e., the repeating unit (AA) represented by the above general formula (II), is preferred. It is also preferable to use a cyclic olefin monomer represented by general formula (IIa) and either a cyclic olefin monomer represented by general formula (IIIa) or (IVa).
  • cyclic olefin monomer represented by the general formula (IIa) it is preferable to use at least one selected from the group consisting of bicyclo[2.2.1]-2-heptene (also called norbornene) and tetracyclo[4.4.0.1 2,5 . 1 7,10 ]-3-dodecene (also called tetracyclododecene), and it is more preferable to use tetracyclo[4.4.0.1 2,5 . 1 7,10 ]-3-dodecene.
  • bicyclo[2.2.1]-2-heptene also called norbornene
  • tetracyclo[4.4.0.1 2,5 . 1 7,10 ]-3-dodecene also called tetracyclododecene
  • the repeating unit (b) in the cyclic olefin copolymer (A) contains a repeating unit derived from at least one selected from the group consisting of bicyclo[2.2.1]-2-heptene and tetracyclo[4.4.0.1 2,5 . 1 7,10 ]-3-dodecene.
  • These cyclic olefin monomers have a rigid ring structure, which has the advantage that the elastic modulus of the copolymer and the molded article is easily maintained.
  • the proportion of repeating units (b) derived from a cyclic olefin monomer in the cyclic olefin copolymer (A) of this embodiment is preferably 5 mol% or more, more preferably 10 mol% or more, even more preferably 15 mol% or more, even more preferably 20 mol% or more, even more preferably 25 mol% or more, even more preferably 30 mol% or more, and even more preferably 35 mol% or more.
  • the proportion of repeating units (b) derived from a cyclic olefin monomer in the cyclic olefin copolymer (A) of this embodiment is preferably 95 mol% or less, more preferably 80 mol% or less, even more preferably 60 mol% or less, even more preferably 50 mol% or less, and even more preferably 40 mol% or less.
  • the proportion of repeating units (b) derived from a cyclic olefin monomer in the cyclic olefin copolymer (A) of this embodiment is preferably 5 mol% or more and 95 mol% or less, more preferably 10 mol% or more and 95 mol% or less, even more preferably 15 mol% or more and 95 mol% or less, even more preferably 20 mol% or more and 80 mol% or less, even more preferably 25 mol% or more and 60 mol% or less, even more preferably 30 mol% or more and 50 mol% or less, and even more preferably 35 mol% or more and 40 mol% or less.
  • the copolymer type of the cyclic olefin copolymer (A) of this embodiment is not particularly limited, but examples include random copolymers and block copolymers.
  • the resin composition of this embodiment from the viewpoint of obtaining molded bodies and optical components with improved transparency, it is preferable to use a random copolymer as the cyclic olefin copolymer (A).
  • the cyclic olefin copolymer (A) of this embodiment preferably contains one or more selected from the group consisting of a random copolymer of ethylene and tetracyclo[4.4.0.1 2,5 . 1 7,10 ]-3-dodecene, a random copolymer of ethylene and bicyclo[ 2.2.1 ]-2-heptene, and a random copolymer of ethylene and tetracyclo[4.4.0.1 2,5 . 1 7,10 ] -3-dodecene and benzonorbornadiene, and more preferably contains one or more selected from the group consisting of a random copolymer of ethylene and tetracyclo[4.4.0.1 2,5 . 1 7,10 ]-3-dodecene and a random copolymer of ethylene and tetracyclo[4.4.0.1 2,5 . 1 7,10 ]-3-dodecene and benzonorbornadiene.
  • the cyclic olefin copolymer (A) may be used alone or in combination of two or more types.
  • the cyclic olefin copolymer (A) of this embodiment can be produced by appropriately selecting the conditions according to the methods described in, for example, JP-A-60-168708, JP-A-61-120816, JP-A-61-115912, JP-A-61-115916, JP-A-61-271308, JP-A-61-272216, JP-A-62-252406, JP-A-62-252407, etc.
  • the cyclic olefin copolymer (A) of this embodiment can improve the heat resistance, transparency, and other optical properties of the cyclic olefin copolymer (A) by contacting the cyclic olefin copolymer (A) or a system containing the cyclic olefin copolymer (A) and the raw material monomer with a hydrogenation catalyst and hydrogen at least once to hydrogenate at least a portion of the unsaturated bonds in the cyclic olefin copolymer (A) and/or the monomer.
  • the hydrogenation, or so-called hydrogenation can be carried out by a conventionally known method.
  • the glass transition point (Tg) of the cyclic olefin copolymer (A) according to this embodiment is preferably 120°C or higher, more preferably 125°C or higher, and even more preferably 130°C or higher.
  • the glass transition point (Tg) of the cyclic olefin copolymer (A) is within the above range, it can obtain better heat resistance, moist heat resistance and transparency when used as an optical component that requires heat resistance, such as an in-vehicle camera lens or a camera lens for a mobile device.
  • the upper limit of the glass transition point (Tg) of the cyclic olefin copolymer (A) according to this embodiment is not particularly limited, but from the viewpoint of moldability, it is preferably 180°C or lower, more preferably 170°C or lower.
  • the glass transition point (Tg) of the cyclic olefin copolymer (A) according to this embodiment is preferably 120° C. or higher and 180° C. or lower, more preferably 125° C. or higher and 180° C. or lower, and even more preferably 130° C. or higher and 170° C. or lower, from the viewpoint of obtaining better heat resistance, moist heat resistance, and transparency when used as an optical component requiring heat resistance, such as an in-vehicle camera lens or a camera lens for a mobile device.
  • the glass transition point (Tg) of the cyclic olefin copolymer (A) according to this embodiment can be measured using a differential scanning calorimeter (DSC).
  • the fatty acid ester composition (B) of this embodiment comprises pentaerythritol (B-1) and a fatty acid ester of pentaerythritol (B-2).
  • the resin composition of the present embodiment contains the fatty acid ester composition (B) and the content of pentaerythritol (B-1) is equal to or less than the upper limit value, so that even thick-walled molded products can have molded articles and optical components with an improved performance balance between moist heat resistance and transparency.
  • the fatty acid ester composition (B) of the present embodiment is preferably a composition obtained by an esterification reaction between pentaerythritol and a fatty acid, and the pentaerythritol (B-1) in the fatty acid ester composition (B) of the present embodiment preferably contains unreacted pentaerythritol that has not been subjected to the esterification reaction.
  • the fatty acid constituting the pentaerythritol fatty acid ester (B-2) preferably contains a fatty acid having 12 to 18 carbon atoms, more preferably contains a fatty acid having 14 to 18 carbon atoms, even more preferably contains a fatty acid having 16 to 18 carbon atoms, and even more preferably contains a fatty acid having 18 carbon atoms.
  • the pentaerythritol fatty acid ester (B-2) preferably contains a compound represented by the following formula (1).
  • RCOOCH2C ( CH2OH ) 3 (1) (In the above formula (1), R is a saturated hydrocarbon group having 11 to 17 carbon atoms.)
  • R is more preferably a saturated hydrocarbon group having 13 to 17 carbon atoms, even more preferably 15 to 17 carbon atoms, and even more preferably 17 carbon atoms.
  • fatty acid esters (B-2) examples include one or more selected from the group consisting of pentaerythritol lauryl, pentaerythritol myristate, pentaerythritol palmitate, pentaerythritol stearate, etc.
  • pentaerythritol stearate is preferred from the viewpoint of obtaining molded articles and optical components having an improved balance of performance between moist heat resistance and transparency, and from the viewpoint of reducing mold contamination during molding of the molded articles and optical components.
  • Such fatty acid ester (B-2) preferably contains one or more selected from the group consisting of monoesters, diesters, triesters and tetraesters.
  • the content of the monoester in the fatty acid ester (B-2) is preferably in the range of 10 mass % or more and 50 mass % or less, more preferably 15 mass % or more and 45 mass % or less, and even more preferably 20 mass % or more and 40 mass % or less, when the total amount of the fatty acid ester (B-2) is taken as 100 mass %, from the viewpoint of obtaining a molded article and an optical component having a further improved performance balance of moist heat resistance and transparency.
  • the total content of diesters and triesters in the fatty acid ester (B-2) may be, for example, 50% by mass or more and 90% by mass or less, 55% by mass or more and 85% by mass or less, or 60% by mass or more and 80% by mass or less.
  • the lower limit of the content of the fatty acid ester composition (B) in the resin composition of this embodiment is preferably 0.05 parts by mass or more, more preferably 0.1 parts by mass or more, even more preferably 0.5 parts by mass or more, even more preferably 1.0 parts by mass or more, and even more preferably 1.5 parts by mass or more, when the content of the cyclic olefin copolymer (A) is 100 parts by mass.
  • the content of the fatty acid ester composition (B) be the above-mentioned lower limit or more, it is possible to obtain a molded body and an optical part with a better balance of performance between moist heat resistance and transparency.
  • the upper limit of the content of the fatty acid ester composition (B) in the resin composition of this embodiment is preferably 5.0 parts by mass or less, more preferably 4.0 parts by mass or less, and even more preferably 3.0 parts by mass or less, when the content of the cyclic olefin copolymer (A) is 100 parts by mass.
  • the content of the fatty acid ester composition (B) in the resin composition of this embodiment is preferably 0.05 parts by mass or more and 5.0 parts by mass or less, more preferably 0.1 parts by mass or more and 5.0 parts by mass or less, even more preferably 0.5 parts by mass or more and 5.0 parts by mass or less, even more preferably 1.0 parts by mass or more and 4.0 parts by mass or less, and even more preferably 1.5 parts by mass or more and 3.0 parts by mass or less, based on 100 parts by mass of the cyclic olefin copolymer (A).
  • the lower limit of the total content of the cyclic olefin copolymer (A) and the fatty acid ester composition (B) in the resin composition of this embodiment is preferably 70% by mass or more, more preferably 80% by mass or more, even more preferably 85% by mass or more, even more preferably 90% by mass or more, even more preferably 95% by mass or more, and even more preferably 98% by mass or more, when the total solid content of the resin composition is 100% by mass.
  • the upper limit of the total content of the cyclic olefin copolymer (A) and the fatty acid ester composition (B) in the resin composition of the present embodiment is not particularly limited, but is, for example, 100 mass % or less.
  • the total content of the cyclic olefin copolymer (A) and the fatty acid ester composition (B) in the resin composition of this embodiment is, when the entire solid content of the resin composition is taken as 100 mass%, preferably 70 mass% or more and 100 mass% or less, more preferably 80 mass% or more and 100 mass% or less, even more preferably 85 mass% or more and 100 mass% or less, even more preferably 90 mass% or more and 100 mass% or less, even more preferably 95 mass% or more and 100 mass% or less, and even more preferably 98 mass% or more and 100 mass% or less.
  • the resin composition of the present embodiment preferably further contains a fatty acid metal salt (C).
  • a fatty acid metal salt (C) By further containing the fatty acid metal salt (C) in the resin composition of this embodiment, the performance balance of the processability of the resulting resin composition and the releasability during injection molding can be improved, and a molded article with better appearance can be obtained.
  • the fatty acid metal salt (C) of the present embodiment preferably contains a metal salt of a long-chain fatty acid having 12 or more carbon atoms.
  • the metal salt of a long-chain fatty acid having 12 or more carbon atoms from the viewpoint of further improving the performance balance of the processability and releasability of the obtained resin composition, preferably, lithium stearate, magnesium stearate, calcium stearate, calcium laurate, calcium ricinoleate, strontium stearate, barium stearate, barium laurate, barium ricinoleate, cadmium stearate, cadmium laurate, cadmium ricinoleate, cadmium naphthenate, cadmium 2-ethylhexoate, zinc laurate, zinc ricinoleate, zinc 2-ethylhexoate, zinc stearate, dibasic zinc
  • the upper limit of the content of the fatty acid metal salt (C) in the resin composition of this embodiment is, when the content of the cyclic olefin copolymer (A) is taken as 100 parts by mass, preferably 0.50 parts by mass or less, more preferably 0.40 parts by mass or less, even more preferably 0.30 parts by mass or less, even more preferably 0.20 parts by mass or less, even more preferably 0.15 parts by mass or less, even more preferably 0.12 parts by mass or less, even more preferably 0.10 parts by mass or less, even more preferably 0.07 parts by mass or less, and even more preferably 0.05 parts by mass or less.
  • the content of the fatty acid metal salt (C) is, from the viewpoint of further improving the performance balance of the processability and releasability of the obtained resin composition and the transparency of a molded article using the resin composition, preferably 0.0001 parts by mass or more and 0.50 parts by mass or less, more preferably 0.0001 parts by mass or more and 0.40 parts by mass or less, even more preferably 0.0005 parts by mass or more and 0.30 parts by mass or less, even more preferably 0.0010 parts by mass or more and 0.20 parts by mass or less, even more preferably 0.0015 parts by mass or more and 0.15 parts by mass or less, even more preferably 0.0020 parts by mass or more and 0.12 parts by mass or less, even more preferably 0.0025 parts by mass or more and 0.10 parts by mass or less, even more preferably 0.0030 parts by mass or more and 0.07 parts by mass or less, and even more preferably 0.0035 parts by mass or more and 0.05 parts by mass or less.
  • the fatty acid metal salt (C) of this embodiment may be contained in the resin composition by simultaneously blending the cyclic olefin copolymer (A), the fatty acid ester composition (B) and the fatty acid metal salt (C), or the fatty acid metal salt (C) may be added later to pellets molded from a resin composition containing the cyclic olefin copolymer (A) and the fatty acid ester composition (B).
  • the fatty acid metal salt (C) of this embodiment may be contained in the resin composition by simultaneously blending the cyclic olefin copolymer (A), the fatty acid ester composition (B), the fatty acid metal salt (C) and the hindered amine compound (D), or the fatty acid metal salt (C) may be added later to pellets molded from a resin composition containing the cyclic olefin copolymer (A), the fatty acid ester composition (B) and the hindered amine compound (D).
  • the resin composition of the present embodiment preferably further contains a hindered amine compound (D).
  • a hindered amine compound (D) By further containing the hindered amine compound (D) in the resin composition of the present embodiment, the light resistance of the obtained resin composition can be improved, and deterioration and discoloration due to UV light can be suppressed.
  • the proportion of carbon atoms in the molecular structure of the hindered amine compound (D) is preferably 67% by mass or more and 80% by mass or less, more preferably 68% by mass or more and 79% by mass or less, and even more preferably 70% by mass or more and 77% by mass or less, from the viewpoint of improving the light resistance of the resulting resin composition.
  • the above percentage of carbon atoms in the molecular structure of the hindered amine compound (D) is a theoretical value calculated from the chemical formula, and this theoretical value is almost the same as the percentage of carbon atoms measured using a CHN elemental analyzer (e.g., CHNS-932, manufactured by LECO, etc.).
  • a CHN elemental analyzer e.g., CHNS-932, manufactured by LECO, etc.
  • the molecular weight of the hindered amine compound (D) is preferably 500 or more and 3500 or less, more preferably 600 or more and 3000 or less, and even more preferably 700 or more and 2000 or less, from the viewpoint of improving the light resistance of the resulting resin composition.
  • the above molecular weight of the hindered amine compound (D) is a theoretical value calculated from the chemical formula, and this theoretical value is approximately equal to the polystyrene equivalent weight average molecular weight measured by gel permeation chromatography (GPC) or the molecular weight measured by mass spectrometry.
  • Examples of hindered amine compounds (D) that satisfy the above characteristics include compounds represented by the following chemical formulas [1] to [37].
  • the solubility of the hindered amine compound (D) in 100 g of hexane at 23°C is preferably 25 g or more, more preferably 50 g or more, and even more preferably 100 g or more, from the viewpoint of improving the light resistance of the resulting resin composition.
  • Hindered amine compounds (D) that satisfy the above hexane solubility can be exemplified by compounds represented by the above chemical formulas [1] to [37].
  • the 5% heat weight loss temperature of the hindered amine compound (D) when heated in nitrogen at a rate of 5°C/min is preferably 300°C or higher, more preferably 320°C or higher, from the viewpoint of improving the light resistance of the resulting resin composition.
  • the heating weight loss temperature can be measured, for example, using a TG/DTA (Thermogrammetry/Differential Thermal Analysis) simultaneous measurement device (e.g. Shimadzu Corporation DTG-60A/60AH).
  • TG/DTA Thermogrammetry/Differential Thermal Analysis
  • Shimadzu Corporation DTG-60A/60AH Shimadzu Corporation DTG-60A/60AH
  • the hindered amine compound (D) of this embodiment preferably includes a hindered amine compound represented by the following general formula (1):
  • n is 1 or 2.
  • R 1 and R 2 may be the same or different and each represents a hydrogen atom or a methyl group, preferably a methyl group. When R 1 and R 2 are methyl groups, coloration of the molded article at high temperatures or in the presence of an acidic substance can be prevented.
  • R 3 , R 4 and R 5 may be the same or different, and can be exemplified by the following (1) to (5).
  • examples of the saturated hydrocarbon group containing an alicyclic skeleton include unsubstituted or cycloalkyl groups having 5 to 12 carbon atoms and 1 to 3 alkyl groups having 1 to 4 carbon atoms.
  • R 3 , R 4 and R 5 may be the same or different, but preferably are (1) a hydrogen atom, (2) an alkyl group having 1 to 24 carbon atoms, or (3) an unsubstituted cycloalkyl group having 5 to 12 carbon atoms and 1 to 3 alkyl groups having 1 to 4 carbon atoms.
  • R 3 , R 4 and R 5 the transmittance on the short wavelength side becomes good, and the compound can be particularly suitably used for optical components.
  • R6 represents an alkylene group having 1 to 4 carbon atoms or a single bond.
  • R 7 may be the same or different, and can be exemplified by the following (1) to (7).
  • R8 is a hydrogen atom or a methyl group, and * represents a bond.
  • R 6 when R 6 is a single bond, the group has a substituent on a carbon atom other than the carbon atom directly bonded to the nitrogen atom.
  • the transmittance at short wavelengths becomes good, and the compound can be suitably used particularly for optical components.
  • Examples of the hindered amine compound represented by the general formula (1) include the compounds represented by the chemical formulas [4] to [37] above.
  • a hindered amine compound represented by the following general formula (2) can be used as the hindered amine compound represented by the following general formula (2).
  • coloring of the molded body at high temperatures can be suppressed.
  • R represents an alkyl group having 1 to 24 carbon atoms.
  • Y is represented by the following general formula:
  • m 0 or 1
  • X and Y are the same as defined above.
  • R represents an alkyl group having 1 to 24 carbon atoms
  • R represents an alkylene group having 1 to 24 carbon atoms. * represents a bond.
  • Each of the multiple X, Y, and R may be the same or different.
  • Examples of the hindered amine compound represented by the general formula (2) include the compounds represented by the chemical formulas [12] to [37] above.
  • the content of the hindered amine compound (D) in the resin composition of this embodiment is preferably 0.05 parts by mass or more and 3.0 parts by mass or less, more preferably 0.10 parts by mass or more and 2.5 parts by mass or less, and even more preferably 0.15 parts by mass or more and 2.3 parts by mass or less, per 100 parts by mass of the cyclic olefin copolymer (A), from the viewpoint of improving the light resistance of the resulting resin composition.
  • the hindered amine compound (D) can be produced by appropriately selecting the conditions according to the methods described in, for example, JP-A-52-73886, JP-A-63-286448, JP-A-5-9356, and JP-A-5-43745.
  • the resin composition of the present embodiment may contain known additives as optional components within a range that does not impair the good physical properties of the resin composition of the present embodiment.
  • the additives include antioxidants, secondary antioxidants, lubricants, release agents, anti-fogging agents, weather stabilizers, light stabilizers, ultraviolet absorbers, and metal deactivators.
  • the upper limit of the internal haze measured by the following (method) is preferably 0.4% or less, more preferably 0.3% or less.
  • the lower limit of the internal haze is not particularly limited, but may be, for example, 0.0% or more, and may be 0.1% or more.
  • the internal haze measured by the following (method) is preferably 0.0% or more and 0.4% or less, more preferably 0.1% or more and 0.3% or less, from the viewpoint of further improving the performance balance of moist heat resistance and transparency in a molded article and an optical component using the resin composition of this embodiment.
  • the resin composition is injection molded using an injection molding machine under conditions of a cylinder temperature of 270° C. and a mold temperature of 126° C. to prepare a test piece having an optical surface of 35 mm ⁇ 65 mm ⁇ thickness of 10 mm.
  • the internal haze of the injection molded test piece is measured using benzyl alcohol with a haze meter based on JIS K7136:2000.
  • the resin composition of this embodiment can be obtained by a method of melt-kneading the cyclic olefin copolymer (A) and the fatty acid ester composition (B) using a known kneading device such as an extruder or a Banbury mixer; a method of dissolving the cyclic olefin copolymer (A) and the fatty acid ester composition (B) in a common solvent and then evaporating the solvent; a method of adding a solution of the cyclic olefin copolymer (A) and the fatty acid ester composition (B) to a poor solvent and causing precipitation; or the like.
  • a known kneading device such as an extruder or a Banbury mixer
  • a method of dissolving the cyclic olefin copolymer (A) and the fatty acid ester composition (B) in a common solvent and then evaporating the solvent a method of adding a
  • the method of mixing the cyclic olefin copolymer (A), the fatty acid ester composition (B), and the fatty acid metal salt (C), or the cyclic olefin copolymer (A), the fatty acid ester composition (B), the fatty acid metal salt (C), and the hindered amine compound (D) is not particularly limited, and the components may be pre-compounded in advance using an extruder or the like, or the components may be dry-blended and then charged into an extruder or the like.
  • the cyclic olefin copolymer (A) and the fatty acid ester composition (B) may be pre-compounded to prepare a resin composition, and the fatty acid metal salt (C) powder may be added to the molded resin composition.
  • the cyclic olefin copolymer (A) and the fatty acid ester composition (B) and the hindered amine compound (D) may be pre-compounded to prepare a resin composition, and the fatty acid metal salt (C) powder may be added to the molded resin composition.
  • the molded article of the present embodiment contains the resin composition of the present embodiment, and therefore the molded article of the present embodiment has an improved balance of performance between moist heat resistance and transparency.
  • the molded article of this embodiment can be suitably used as an optical component in an optical system that requires highly accurate identification of an image.
  • Optical components are components used in optical equipment, etc., and specific examples include lenses for various sensors, pickup lenses, projector lenses, prisms, f ⁇ lenses, imaging lenses, light guide plates, lenses for head-mounted displays, etc., and from the viewpoint of the effects of this embodiment, the molded article can be suitably used as an f ⁇ lens, imaging lens, lens for a sensor, prism, or light guide plate.
  • the method of molding the resin composition of this embodiment to obtain a molded product is not particularly limited, and known methods can be used. Depending on the application and shape, for example, extrusion molding, injection molding, inflation molding, blow molding, extrusion blow molding, injection blow molding, press molding, vacuum molding, powder slush molding, calendar molding, foam molding, etc. can be applied. Among these, injection molding is preferred from the viewpoint of moldability and productivity. Furthermore, molding conditions are appropriately selected depending on the purpose of use or molding method, and for example, the resin temperature in injection molding is appropriately selected within the range of, for example, usually 150°C to 400°C, preferably 200°C to 350°C, and more preferably 230°C to 330°C.
  • Example 1 ⁇ Polymerization of Cyclic Olefin Copolymer (A)> (Preparation of catalyst) Ethyl aluminum sesquichloride (Al(C 2 H 5 ) 1.5 Cl 1.5 ) was diluted using cyclohexane as a solvent to prepare an organoaluminum compound catalyst solution.
  • a copolymer solution was obtained by continuously copolymerizing ethylene and tetracyclo[ 4.4.0.12,5.17,10 ]-3- dodecene in a stirred polymerization reactor.
  • the organoaluminum compound catalyst solution prepared in the above (Catalyst Preparation) was used as the catalyst, and ethylene was supplied into the polymerization reactor together with hydrogen gas.
  • molten cyclic olefin copolymer (A) (a random copolymer of ethylene and tetracyclo[4.4.0.1 2,5 .1 7,10 ]-3-dodecene).
  • repeating units constituting the cyclic olefin copolymer (A) When the total amount of repeating units constituting the cyclic olefin copolymer (A) is taken as 100 mol %, the content of repeating units derived from ethylene (repeating units (a)) was 62 mol %, and the content of repeating units derived from tetracyclo[ 4.4.0.12,5.17,10 ]-3- dodecene (repeating units (b)) was 38 mol %.
  • the contents of the repeating unit (a) derived from ethylene constituting the cyclic olefin copolymer (A) and the repeating unit (b) derived from tetracyclo[ 4.4.0.12,5.17,10 ]-3- dodecene were measured using a JEOL "ECA500" nuclear magnetic resonance apparatus under the following conditions.
  • the hindered amine compound (D-1) (N,N',N"-tridodecyl-N,N',N"-tris-(1,2,2,6,6-pentamethyl-4-piperidinyl)-[1,3,5]-triazine-2,4,6-triamine (T12M)) represented by chemical formula [35] was synthesized by the following method.
  • TADA N-dodecyl-2,2,6,6-tetramethylpiperidin-4-amine
  • Example 2 A resin composition was prepared in the same manner as in Example 1, except that the fatty acid ester composition (Ba) in Example 1 was changed to a fatty acid ester composition (Bb) (content of pentaerythritol (B-1) in fatty acid ester composition (Bb): 1.5% by mass) consisting of pentaerythritol (B-1) and a fatty acid ester of pentaerythritol (mixture of pentaerythritol monostearate: 32% by mass, pentaerythritol distearate: 45% by mass, and pentaerythritol tristearate: 23% by mass) (B-2).
  • the glass transition temperature (Tg) of the resin composition was 137°C.
  • Example 5 A resin composition was prepared in the same manner as in Example 1, except that the fatty acid ester composition (Ba) in Example 1 was changed to a fatty acid ester composition (Bd) (content of pentaerythritol (B-1) in fatty acid ester composition (Bd): 2.5% by mass) consisting of pentaerythritol (B-1) and a fatty acid ester of pentaerythritol (mixture of pentaerythritol monostearate: 32% by mass, pentaerythritol distearate: 45% by mass, and pentaerythritol tristearate: 23% by mass) (B-2).
  • the glass transition temperature (Tg) of the resin composition was 137°C.
  • Example 6 A resin composition was prepared in the same manner as in Example 1, except that the fatty acid ester composition (Ba) in Example 1 was changed to a fatty acid ester composition (Be) (content of pentaerythritol (B-1) in fatty acid ester composition (Be): 4.5% by mass) consisting of pentaerythritol (B-1) and a fatty acid ester of pentaerythritol (mixture of pentaerythritol monostearate: 32% by mass, pentaerythritol distearate: 45% by mass, and pentaerythritol tristearate: 23% by mass) (B-2).
  • the glass transition temperature (Tg) of the resin composition was 137°C.
  • Example 7 A resin composition was prepared in the same manner as in Example 6, except that 0.04 parts by mass of zinc stearate (C-1) was added during the extrusion step.
  • the glass transition temperature (Tg) of the resin composition was 137°C.
  • Example 8 A resin composition was prepared in the same manner as in Example 1, except that 0.001 parts by mass of calcium stearate (C-2) was added during the extrusion step.
  • the glass transition temperature (Tg) of the resin composition was 137°C.
  • Example 9 A resin composition was prepared in the same manner as in Example 1, except that 0.6 parts by mass of a hindered amine compound ((D-1), compound name: N,N',N"-tridodecyl-N,N',N"-tris-(1,2,2,6,6-pentamethyl-4-piperidinyl)-[1,3,5]-triazine-2,4,6-triamine (T12M)) was added during the extrusion step.
  • the glass transition temperature (Tg) of the resin composition was 135°C.
  • Example 10 A resin composition was prepared in the same manner as in Example 2, except that 0.04 parts by mass of zinc stearate (C-1) and 0.4 parts by mass of the hindered amine compound (D-1) were added during the extrusion step.
  • the glass transition temperature (Tg) of the resin composition was 136°C.
  • Example 17 A resin composition was prepared in the same manner as in Example 10, except that zinc stearate (C-1) was not added during the extrusion process, and 0.04 parts by mass of zinc stearate (C-1) was added after the extrusion process.
  • the glass transition temperature (Tg) of the resin composition was 136°C.
  • Example 1 A pelletized resin composition was obtained in the same manner as in Example 1, except that the fatty acid ester composition (Ba) was not used in the extrusion step in Example 1.
  • the glass transition temperature (Tg) of the resin composition was 150°C.
  • a resin composition was prepared in the same manner as in Example 1, except that the fatty acid ester composition (Ba) in Example 1 was changed to a fatty acid ester composition (Bc) (content of pentaerythritol (B-1) in fatty acid ester composition (Bc): 5.5% by mass) consisting of pentaerythritol (B-1) and a fatty acid ester of pentaerythritol (mixture of pentaerythritol monostearate: 32% by mass, pentaerythritol distearate: 45% by mass, and pentaerythritol tristearate: 23% by mass) (B-2).
  • the glass transition temperature (Tg) of the resin composition was 137°C.
  • a resin composition was prepared in the same manner as in Example 1, except that the fatty acid ester composition (Ba) in Example 1 was changed to a fatty acid ester composition (Bf) (content of pentaerythritol (B-1) in fatty acid ester composition (Bf): 10.5% by mass) consisting of pentaerythritol (B-1) and a fatty acid ester of pentaerythritol (mixture of pentaerythritol monostearate: 32% by mass, pentaerythritol distearate: 45% by mass, and pentaerythritol tristearate: 23% by mass) (B-2).
  • the glass transition temperature (Tg) of the resin composition was 137°C.
  • Example 3 The deashed copolymer solution obtained in the same manner as in Example 1 was continuously hydrogenated using a nickel/diatomaceous earth catalyst (N112 manufactured by JGC Chemical) under the conditions of a reaction temperature of 100°C, a reaction pressure of 1 MPa, and an LHSV of 5/hr.
  • N112 nickel/diatomaceous earth catalyst
  • pentaerythrityl-tetrakis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate] was added as a stabilizer in an amount of 0.4% by mass based on the entire copolymer solution, and the mixture was mixed in a stirring tank for 1 hour. Thereafter, the solvent was removed in the same manner as in Example 1, and a hydrogenated cyclic olefin copolymer (Aa) was obtained.
  • Example 4 A resin composition was prepared in the same manner as in Example 3, except that the fatty acid ester composition (Ba) in Example 3 was changed to a fatty acid ester composition (Bb) (content of pentaerythritol (B-1) in fatty acid ester composition (Bb): 1.5% by mass) consisting of pentaerythritol (B-1) and a fatty acid ester of pentaerythritol (mixture of pentaerythritol monostearate: 32% by mass, pentaerythritol distearate: 45% by mass, and pentaerythritol tristearate: 23% by mass) (B-2).
  • the glass transition temperature (Tg) of the resin composition was 139°C.
  • Example 11 A resin composition was prepared in the same manner as in Example 3, except that the fatty acid ester composition (Ba) in Example 3 was changed to a fatty acid ester composition (Bd) (content of pentaerythritol (B-1) in fatty acid ester composition (Bd): 2.5% by mass) consisting of pentaerythritol (B-1) and a fatty acid ester of pentaerythritol (mixture of pentaerythritol monostearate: 32% by mass, pentaerythritol distearate: 45% by mass, and pentaerythritol tristearate: 23% by mass) (B-2).
  • the glass transition temperature (Tg) of the resin composition was 139°C.
  • Example 12 A resin composition was prepared in the same manner as in Example 3, except that the fatty acid ester composition (Ba) in Example 3 was changed to a fatty acid ester composition (Be) (content of pentaerythritol (B-1) in fatty acid ester composition (Be): 4.5% by mass) consisting of pentaerythritol (B-1) and a fatty acid ester of pentaerythritol (mixture of pentaerythritol monostearate: 32% by mass, pentaerythritol distearate: 45% by mass, and pentaerythritol tristearate: 23% by mass) (B-2).
  • the glass transition temperature (Tg) of the resin composition was 139°C.
  • Example 13 A resin composition was prepared in the same manner as in Example 12, except that 0.04 parts by mass of zinc stearate (C-1) was added during the extrusion step.
  • the glass transition temperature (Tg) of the resin composition was 139°C.
  • Example 14 A resin composition was prepared in the same manner as in Example 12, except that 0.001 parts by mass of calcium stearate (C-2) was added during the extrusion step.
  • the glass transition temperature (Tg) of the resin composition was 139°C.
  • Example 15 A resin composition was prepared in the same manner as in Example 3, except that 0.6 parts by mass of the hindered amine compound (D-1) was added during the extrusion step.
  • the glass transition temperature (Tg) of the resin composition was 137°C.
  • Example 16 A resin composition was prepared in the same manner as in Example 4, except that 0.04 parts by mass of zinc stearate (C-1) and 0.4 parts by mass of the hindered amine compound (D-1) were added during the extrusion step.
  • the glass transition temperature (Tg) of the resin composition was 138°C.
  • Example 18 A resin composition was prepared in the same manner as in Example 16, except that zinc stearate (C-1) was not added during the extrusion process, and 0.04 parts by mass of zinc stearate (C-1) was added after the extrusion process.
  • the glass transition temperature (Tg) of the resin composition was 136°C.
  • Example 3 A pelletized resin composition was obtained in the same manner as in Example 3, except that the fatty acid ester composition (Ba) was not used in the extrusion step in Example 3.
  • the glass transition temperature (Tg) of the resin composition was 152°C.
  • a resin composition was prepared in the same manner as in Example 3, except that the fatty acid ester composition (Ba) in Example 3 was changed to a fatty acid ester composition (Bc) (content of pentaerythritol (B-1) in fatty acid ester composition (Bc): 5.5% by mass) consisting of pentaerythritol (B-1) and a fatty acid ester of pentaerythritol (mixture of pentaerythritol monostearate: 32% by mass, pentaerythritol distearate: 45% by mass, and pentaerythritol tristearate: 23% by mass) (B-2).
  • the glass transition temperature (Tg) of the resin composition was 139°C.
  • a resin composition was prepared in the same manner as in Example 3, except that the fatty acid ester composition (Ba) in Example 3 was changed to a fatty acid ester composition (Bf) (content of pentaerythritol (B-1) in fatty acid ester composition (Bf): 10.5% by mass) consisting of pentaerythritol (B-1) and a fatty acid ester of pentaerythritol (mixture of pentaerythritol monostearate: 32% by mass, pentaerythritol distearate: 45% by mass, and pentaerythritol tristearate: 23% by mass) (B-2).
  • the glass transition temperature (Tg) of the resin composition was 139°C.
  • the glass transition temperature of the resin composition was measured using a differential scanning calorimeter.
  • the glass transition temperature (Tg) of the resin composition was measured under a nitrogen atmosphere using a Discovery DSC-2500 manufactured by TA Instruments.
  • the resin composition was heated from room temperature (23°C) to 200°C at a heating rate of 10°C/min and then held for 5 minutes.
  • the temperature was then lowered to -20°C at a heating rate of 10°C/min and then held for 5 minutes.
  • the glass transition temperature (Tg) of the resin composition was determined from the endothermic curve when the temperature was raised to 200°C at a heating rate of 10°C/min.
  • test piece of the square plate molded body and the cylindrical molded body was left in an atmosphere of 65°C and 90% relative humidity for 168 hours to carry out a moist heat resistance test. After that, it was taken out and left in an atmosphere of 23°C and 50% relative humidity for 48 hours.
  • the internal haze of these test pieces was measured using a haze meter based on JIS K7136:2000 using benzyl alcohol.
  • ⁇ internal haze (the difference between the internal haze after the moist heat resistance test and the internal haze before the moist heat resistance test) was used as an index of moist heat resistance, and a ⁇ internal haze of 1.0% or less was considered to be acceptable, and a ⁇ internal haze of more than 1.0% was considered to be unacceptable.
  • the transmittance of the test pieces before and after the light resistance test was measured using a UV-visible spectrophotometer (Hitachi High-Tech Science Corporation; UH5700), and the transmittance difference ( ⁇ transmittance) at 450 nm before and after the light resistance test was evaluated as A when it was within -5 points, B when it was -5 to -10 points, and C when it was over -10 points.
  • the resin compositions described in Examples 7 to 8, 10, 13 to 14, and 16 to 18, which further contained a fatty acid metal salt (C) had improved release properties while maintaining the balance of moist heat resistance and transparency compared to resin compositions that did not contain a fatty acid metal salt (C).
  • Examples 9, 10, and 15 to 18, which further contained a hindered amine compound (D) had improved light resistance compared to resin compositions that did not contain a hindered amine compound (D).

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PCT/JP2024/033632 2023-09-26 2024-09-20 樹脂組成物、成形体および光学部品 Pending WO2025070288A1 (ja)

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