Resin composition for optical component, molded article, and optical component
The resin composition with cyclic olefin copolymer and fatty acid ester composition addresses the need for improved moisture and heat resistance in optical components by optimizing pentaerythritol content, achieving balanced performance in thick designs.
Patent Information
- Application Number
- JP2025139460
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2023-09-26
- Filing Date
- 2025-08-25
- Publication Date
- 2025-11-26
- Estimated Expiration
- 2044-09-20
AI Technical Summary
Optical components require improved moisture and heat resistance, particularly in thicker designs, to enhance design flexibility while maintaining transparency.
A resin composition comprising a cyclic olefin copolymer and a fatty acid ester composition with pentaerythritol within specific content ranges, specifically 5.0 mass% or less, enhances the balance between moist heat resistance and transparency.
The resin composition produces molded articles and optical components with improved performance balance between moist heat resistance and transparency, even in thick designs, by uniformly dispersing pentaerythritol in the cyclic olefin copolymer without phase separation.
Smart Images

Figure 2025172809000001 
Figure 2025172809000002 
Figure 2025172809000003
Abstract
Description
[Technical Field]
[0001] The present invention relates to a resin composition, a molded article, and an optical component. [Background technology]
[0002] Cyclic olefin copolymer resin compositions have excellent optical properties and are therefore used, for example, as optical components such as optical lenses. As a technique relating to a cyclic olefin resin composition used for optical parts, for example, the technique described in Patent Document 1 can be mentioned.
[0003] Patent Document 1 discloses a method for producing a thermoplastic norbornene-based resin composition that exhibits sufficient mold releasability in melt molding or the like, does not generate voids, and has the heat resistance, chemical resistance, electrical properties, etc. of a thermoplastic norbornene-based resin, and a method for producing a thermoplastic norbornene-based resin composition that exhibits sufficient mold releasability in melt molding or the like, does not generate voids, and has the heat resistance, chemical resistance, electrical properties, etc. of a thermoplastic norbornene-based resin, and n (wherein n represents a natural number, R represents a hydrocarbon group which may have a hydroxyl group, and X represents a hydroxyacyloxy group. However, when n is 2 or more, the n Xs may or may not be the same. The total number of carbon atoms in the formula is 16 or more.) and / or a resin composition comprising a compound represented by the following formula is disclosed: [Prior art documents] [Patent documents]
[0004] [Patent Document 1] Japanese Patent Application Publication No. 9-241484 Summary of the Invention [Problem to be solved by the invention]
[0005] In recent years, optical components have been required to have further improvements in moisture and heat resistance and transparency when they are thick, in order to increase the degree of freedom in design. The present invention has been made in view of the above circumstances, and provides a resin composition from which molded articles and optical components having an improved performance balance between moist heat resistance and transparency can be obtained, as well as a molded article and optical component having an improved performance balance between moist heat resistance and transparency. [Means for solving the problem]
[0006] The present inventors have conducted extensive research to achieve the above object, and as a result have found that by using a fatty acid ester composition having a pentaerythritol content within a specific range, it is possible to provide a resin composition from which a molded article and an optical component having an improved performance balance between moist heat resistance and transparency can be obtained, and a molded article and an optical component having an improved performance balance between moist heat resistance and transparency, thereby completing the present invention.
[0007] That is, according to the present invention, there are provided the following resin composition, molded article, and optical component.
[0008] [1] a cyclic olefin copolymer (A); a fatty acid ester composition (B) consisting of pentaerythritol (B-1) and a fatty acid ester of pentaerythritol (B-2); 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 pentaerythritol (B-1) and the pentaerythritol fatty acid ester (B-2) in the fatty acid ester composition (B) is 100 mass%. [ka] (In the above general formula (I), R 300 represents a hydrogen atom or a linear or branched hydrocarbon group having 1 to 29 carbon atoms. [ka] (In the above general formula (II), u is 0 or 1, v is 0 or a positive integer, w is 0 or 1, and R 61 ~R 78 and 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; R 75 ~R 78 may be bonded to each other to form a monocyclic or polycyclic ring. [ka] (In the above general formula (III), x and d are integers of 0 or 1 or more, y and z are 0, 1 or 2, and R 81 ~R 99 may be the same or different and are a hydrogen atom, a halogen atom, an aliphatic hydrocarbon group which is an alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 3 to 15 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, or an alkoxy group; R 89 and R 90 and the carbon atom to which R is bonded. 93 or the carbon atom to which R is attached 91 may be bonded directly or via an alkylene group having 1 to 3 carbon atoms, and when y=z=0, R 95 and R 92 or R 95 and R 99 may be bonded to each other to form a monocyclic or polycyclic aromatic ring. [ka] (In the above general formula (IV), R 100 , 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. [2] In the resin composition described in [1] above, A resin composition, wherein the content of the pentaerythritol (B-1) in the fatty acid ester composition (B) is 3.0 mass% or less, when the total content of the pentaerythritol (B-1) and the pentaerythritol fatty acid ester (B-2) in the fatty acid ester composition (B) is 100 mass%. [3] In the resin composition according to the above [1] or [2], A resin composition in which the fatty acid constituting the pentaerythritol fatty acid ester (B-2) contains a fatty acid having 12 to 18 carbon atoms. [4] In the resin composition according to any one of the above [1] to [3], A resin composition, wherein the pentaerythritol fatty acid ester (B-2) 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.) [5] In the resin composition according to any one of the above [1] to [4], A resin composition in which the fatty acid ester of pentaerythritol (B-2) contains pentaerythritol monostearate. [6] In the resin composition according to any one of the above [1] to [5], A resin composition in which the content of the fatty acid ester composition (B) is 0.05 parts by mass or more and 5.0 parts by mass or less, relative to 100 parts by mass of the content of the cyclic olefin copolymer (A). [7] In the resin composition according to any one of the above [1] to [6], A resin composition in which the total content of the cyclic olefin copolymer (A) and the fatty acid ester composition (B) is 70% by mass or more and 100% by mass or less, when the total solid content of the resin composition is 100% by mass. [8] In the resin composition according to any one of the above [1] to [7], A resin composition further comprising a fatty acid metal salt (C). [9] In the resin composition according to any one of the above [1] to [8], The resin composition, wherein the fatty acid metal salt (C) comprises a metal salt of a long-chain fatty acid having 12 or more carbon atoms.
[10] In the resin composition according to any one of the above [1] to [9], A resin composition in which the content of the fatty acid metal salt (C) is 0.0001 part by mass or more and 0.50 part by mass or less per 100 parts by mass of the cyclic olefin copolymer (A).
[11] In the resin composition according to any one of the above [1] to
[10] , The resin composition further comprises a hindered amine compound (D).
[12] In the resin composition according to the above
[11] , 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 per 100 parts by mass of the cyclic olefin copolymer (A).
[13] In the resin composition according to any one of the above [1] to
[12] , When the total of the repeating units constituting the cyclic olefin copolymer (A) is taken as 100 mol %, A resin composition in which the proportion of the repeating unit (a) in the cyclic olefin copolymer (A) is 5 mol % or more and 95 mol % or less.
[14] In the resin composition according to any one of the above [1] to
[13] , A resin composition in which the repeating unit (a) in the cyclic olefin copolymer (A) contains a repeating unit derived from ethylene.
[15] In the resin composition according to any one of the above [1] to
[14] , When the total of the repeating units constituting the cyclic olefin copolymer (A) is taken as 100 mol %, A resin composition in which the proportion of the repeating unit (b) in the cyclic olefin copolymer (A) is 5 mol % or more and 95 mol % or less.
[16] In the resin composition according to any one of the above [1] to
[15] , A resin composition in which the repeating unit (b) in the cyclic olefin copolymer (A) contains a repeating unit (AA) represented by the general formula (II).
[17] In the resin composition according to any one of the above [1] to
[16] , The repeating unit (b) in the cyclic olefin copolymer (A) is a bicyclo[2.2.1]-2-heptene and tetracyclo[4.4.0.1]heptene. 2,5 .1 7,10 ]-3-dodecene.
[18] In the resin composition according to any one of the above [1] to
[17] , The cyclic olefin copolymer (A) is a copolymer of ethylene and tetracyclo[4.4.0.1 2,5 .1 7,10 ]-3-dodecene, random copolymers of ethylene and bicyclo[2.2.1]-2-heptene, and random copolymers of ethylene and tetracyclo[4.4.0.1 2,5 .1 7,10 A resin composition comprising one or more members selected from the group consisting of random copolymers of 1-(2-methyl-2-propanediol)-3-dodecene and benzonorbornadiene.
[19] In the resin composition according to any one of the above [1] to
[18] , A resin composition having an internal haze of 0.4% or less as measured by the following (method). (method) 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 with an optical surface measuring 35 mm x 65 mm x 10 mm thick. The internal haze of the injection-molded test piece is measured using benzyl alcohol with a haze meter according to JIS K7136:2000.
[20] A molded article comprising the resin composition according to any one of the above [1] to
[19] . [twenty one] An optical component comprising the molded article according to
[20] above. [Effects of the Invention]
[0009] According to the present invention, it is possible to provide a resin composition that can produce molded articles and optical components having an improved performance balance between moist heat resistance and transparency, as well as a molded article and optical component having an improved performance balance between moist heat resistance and transparency. DETAILED DESCRIPTION OF THE INVENTION
[0010] The present invention will be described below based on embodiments.
[0011] <Resin composition> First, the resin composition of the present embodiment will be described. The resin composition of this embodiment is a resin composition comprising a cyclic olefin copolymer (A) and a fatty acid ester composition (B) comprising pentaerythritol (B-1) and a pentaerythritol fatty acid ester (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% or less, when the total content of the pentaerythritol (B-1) and the pentaerythritol fatty acid ester (B-2) in the fatty acid ester composition (B) is 100 mass%.
[0012] [ka]
[0013] In the above general formula (I), R 300 represents a hydrogen atom or a linear or branched hydrocarbon group having 1 to 29 carbon atoms.
[0014] [ka]
[0015] In the above general formula (II), 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, and R 61 ~R 78 and 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; R75 ~R 78 may be bonded to each other to form a monocyclic or polycyclic ring.
[0016] [ka]
[0017] In the above general formula (III), x and d are 0 or an integer of 1 or more, preferably an integer of 0 or more and 2 or less, more preferably 0 or 1, y and z are 0, 1, or 2, and R 81 ~R 99 may be the same or different and are a hydrogen atom, a halogen atom, an aliphatic hydrocarbon group which is an alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 3 to 15 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, or an alkoxy group; R 89 and R 90 and the carbon atom to which R is bonded. 93 or the carbon atom to which R is attached 91 may be bonded directly or via an alkylene group having 1 to 3 carbon atoms, and when y=z=0, R 95 and R 92 or R 95 and R 99 may be bonded to each other to form a monocyclic or polycyclic aromatic ring.
[0018] [ka]
[0019] In the above general formula (IV), R 100 , 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.
[0020] According to the resin composition of this 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. Although the reason for this is unclear, it is believed that when the content of pentaerythritol in the fatty acid ester composition (B) is within a specific range, the more polar pentaerythritol is dispersed uniformly in the less polar cyclic olefin copolymer (A) without phase separation, thereby improving the performance balance between the moist heat resistance and transparency of the resulting molded body and optical component. As described above, 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 molded articles and optical components are produced.
[0021] 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, and even more preferably 0.5% by mass or less, when the total content of pentaerythritol (B-1) and the pentaerythritol fatty acid ester (B-2) in the fatty acid ester composition (B) is taken as 100% by mass. By keeping the content of pentaerythritol (B-1) at or below the upper limit, the performance balance between moist heat resistance and transparency of molded articles and optical components using the resin composition of this embodiment can be improved. Furthermore, 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, 0.05 mass% or more, 0.1 mass% or more, 0.3 mass% or more, or 0.4 mass% or more. Furthermore, from the viewpoint of improving the balance of performance between moist heat resistance and transparency of a molded article and an optical component using the resin composition of this embodiment, the content of pentaerythritol (B-1) in the fatty acid ester composition (B) of this embodiment is preferably 0.01% by mass or more and 5.0% by mass or less, more preferably 0.01% by mass or more and 4.0% 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. 0.5% by mass or less, more preferably 0.01% by mass or more and 3.0% by mass or less, even more preferably 0.01% by mass or more and 2.5% by mass or less, even more preferably 0.01% by mass or more and 2.0% by mass or less, even more preferably 0.01% by mass or more and 1.8% by mass or less, even more preferably 0.05% by mass or more and 1.5% by mass or less, even more preferably 0.1% by mass or more and 1.0% by mass or less, even more preferably 0.3% by mass or more and 0.8% by mass or less, and even more preferably 0.4% by mass or more and 0.5% by mass or less.
[0022] 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 determining the content by gas chromatography. Specifically, the following measurement conditions can be exemplified: Measuring equipment: 6890N (Agilent Technologies) Column: DB-1HT (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 this embodiment can be measured by the method described in paragraphs 0168 to 0170 of Japanese Patent No. 5778884.
[0023] Each component will be specifically described below.
[0024] [Cyclic olefin copolymer (A)] The cyclic olefin copolymer (A) in the resin composition of this embodiment contains at least one olefin-derived repeating unit (a) represented by the general formula (I) above, and at least one cyclic olefin monomer-derived repeating unit (b) selected from the group consisting of repeating units (AA) represented by the general formula (II) above, repeating units (AB) represented by the general formula (III) above, and repeating units (AC) represented by the general formula (IV) above.
[0025] 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) corresponding to the above general formula (I) is used.
[0026] [ka]
[0027] In the above general formula (I) and the above general formula (Ia), R 300represents 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, and 1-eicosene. Among these, the olefin monomer represented by the general formula (Ia) is preferably at least one selected from ethylene and propylene, and more preferably ethylene, from the viewpoint of obtaining a molded article having superior 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, and 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. Furthermore, the olefin monomer may contain at least one biomass-derived monomer (ethylene, propylene, α-olefin).
[0028] When the total number of repeating units constituting the cyclic olefin copolymer (A) of this embodiment is taken as 100 mol %, from the viewpoint of obtaining a molded article having better heat resistance, mechanical properties, and optical properties, 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. Furthermore, when the total number of repeating units constituting the cyclic olefin copolymer (A) of this embodiment is taken as 100 mol%, from the viewpoint of obtaining a molded article having better heat resistance, mechanical properties, and optical properties, 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. Furthermore, when the total number of repeating units constituting the cyclic olefin copolymer (A) of this embodiment is taken as 100 mol%, from the viewpoint of obtaining a molded article having better heat resistance, mechanical properties, and optical properties, the proportion of olefin-derived repeating units (a) 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 olefin is: 13 It can be measured by C-NMR.
[0029] 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 the repeating unit (b) derived from the cyclic olefin monomer represented by the general formula (II), (III), or (IV). Specifically, the cyclic olefin monomers represented by the general formulas (IIa), (IIIa), and (IVa), which correspond to the general formulas (II), (III), and (IV), respectively, are used.
[0030] [ka]
[0031] In the above general formula (II) and general formula (IIa), 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, and R 61 ~R 78 and 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; R 75 ~R 78 may be bonded to each other to form a monocyclic or polycyclic ring.
[0032] [ka]
[0033] In the above general formula (III) and general formula (IIIa), x and d are 0 or an integer of 1 or more, preferably an integer of 0 or more and 2 or less, more preferably 0 or 1, y and z are 0, 1 or 2, and R 81 ~R 99 may be the same or different and are a hydrogen atom, a halogen atom, an aliphatic hydrocarbon group which is an alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 3 to 15 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, or an alkoxy group; R 89 and R 90 and the carbon atom to which R is bonded. 93 or the carbon atom to which R is attached 91 may be bonded directly or via an alkylene group having 1 to 3 carbon atoms, and when y=z=0, R 95 and R 92 or R 95 and R 99 may be bonded to each other to form a monocyclic or polycyclic aromatic ring.
[0034] [ka]
[0035] In the above general formula (IV) and general formula (IVa), R 100 , 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.
[0036] 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 the copolymerization component, the solubility of the cyclic olefin copolymer (A) in a solvent is further improved, resulting in good moldability and improved product yield.
[0037] Specific examples of the cyclic olefin monomer represented by general formula (IIa), (IIIa), or (IVa) include the compounds described in paragraphs 0037 to 0063 of WO 2006 / 118261. The cyclic olefin monomer is obtained from dicyclopentadiene and ethylene, and the ethylene may contain units derived from a biomass-derived monomer (ethylene).
[0038] Specifically, 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, heptacyclo-5-eicosene derivatives conductors, 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, and cycloalkylene derivatives having 3 to 20 carbon atoms.
[0039] As the repeating unit (b) in the cyclic olefin copolymer (A), a repeating unit derived from the 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 a cyclic olefin monomer represented by general formula (IIIa) or (IVa).
[0040] The cyclic olefin monomers represented by the general formula (IIa) include 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 at least one selected from the group consisting of tetracyclo[4.4.0.1 2,5 .1 7,10It is more preferable to use bicyclo[2.2.1]-2-heptene and tetracyclo[4.4.0.1]-3-dodecene as the repeating unit (b) in the cyclic olefin copolymer (A). 2,5 .1 7,10 It is preferable that the repeating unit is derived from at least one selected from the group consisting of 1-(2-methyl-2-propanediol), 2-(2-methyl-2-propanediol), 3-(2-methyl-2-propanediol), 4-(2-methyl-2-propanediol), 5-(2-methyl-2-propanediol), 6-(2-methyl-2-propanediol), 7-(2-methyl-2-propanediol), 8-(2-methyl-2-propanediol), 9-(2-methyl-2-propanediol), 10-(2-methyl-2-propanediol), 11-(2-methyl-2-propanediol), 12-(2-methyl-2-propanediol), 13-(2-methyl-2-propanediol), 14-(2-methyl-2-propanediol), 15-(2-methyl-2-propanediol), 16-(2-methyl-2-propanediol), 17-(2-methyl-2-propanediol), 18-(2-methyl-2-propanediol), 20-(2-methyl-2-propanediol), 21-(2-methyl-2-propanediol), 22-(2-methyl-2-propanediol), 23-(2-methyl-2-propanediol), 24-(2-methyl-2-propanediol), 25-(2-methyl-2-propanediol), 26-(2-methyl-2-propanediol), 27-(2-methyl-2-propanediol), 28-(2-methyl-2-propanediol), 29-(2-methyl-2-propanediol), 30-(2-methyl-2-propanediol), 31-(2-methyl-2-propanediol), 32-(2-methyl-2-propanediol), 33-
[0041] When the total number of repeating units constituting the cyclic olefin copolymer (A) of this embodiment is taken as 100 mol%, from the viewpoint of obtaining a molded article having better heat resistance, mechanical properties, and optical properties, the proportion of repeating units (b) derived from cyclic olefin monomers 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. Furthermore, when the total number of repeating units constituting the cyclic olefin copolymer (A) of this embodiment is taken as 100 mol%, from the viewpoint of obtaining a molded article having better heat resistance, mechanical properties, and optical properties, the proportion of repeating units (b) derived from cyclic olefin monomers 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. Furthermore, when the total number of repeating units constituting the cyclic olefin copolymer (A) of this embodiment is taken as 100 mol%, from the viewpoint of obtaining a molded article having better heat resistance, mechanical properties, and optical properties, the proportion of repeating units (b) derived from cyclic olefin monomers 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.
[0042] The copolymerization type of the cyclic olefin copolymer (A) of this embodiment is not particularly limited, and examples thereof include random copolymers, block copolymers, etc. In the resin composition of this embodiment, it is preferable to use a random copolymer as the cyclic olefin copolymer (A) from the viewpoint of obtaining molded articles and optical components with improved transparency.
[0043] The cyclic olefin copolymer (A) of this embodiment is a copolymer of ethylene and tetracyclo[4.4.0.1 2,5 .1 7,10 ]-3-dodecene, random copolymers of ethylene and bicyclo[2.2.1]-2-heptene, and random copolymers of ethylene and tetracyclo[4.4.0.1 2,5 .1 7,10 ]-3-dodecene and benzonorbornadiene random copolymers, and 2,5 .1 7,10 ]-3-dodecene and ethylene with tetracyclo[4.4.0.1 2,5 .1 7,10 It is more preferable that the copolymer contains one or more members selected from the group consisting of random copolymers of 1-(2-methyl-2-propanediol)-3-dodecene and benzonorbornadiene.
[0044] In the present embodiment, the cyclic olefin copolymer (A) may be used alone or in combination of two or more.
[0045] The cyclic olefin copolymer (A) of this embodiment can be produced by appropriately selecting 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.
[0046] The cyclic olefin copolymer (A) of this embodiment can improve optical properties such as heat resistance and transparency by contacting the cyclic olefin copolymer (A) or a system containing the cyclic olefin copolymer (A) and the raw material monomers 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 monomers. The hydrogenation, or so-called hydrogenation, can be carried out by a conventionally known method.
[0047] The glass transition temperature (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. When the glass transition temperature (Tg) of the cyclic olefin copolymer (A) is within the above range, better heat resistance, moist heat resistance, and transparency can be obtained when the cyclic olefin copolymer (A) is used as an optical component requiring heat resistance, such as an in-vehicle camera lens or a camera lens for a mobile device. The upper limit of the glass transition temperature (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 that requires heat resistance, such as an in-vehicle camera lens or a camera lens for a mobile device.
[0048] The glass transition temperature (Tg) of the cyclic olefin copolymer (A) according to this embodiment can be measured using a differential scanning calorimeter (DSC).
[0049] [Fatty acid ester composition (B)] 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 this embodiment contains the fatty acid ester composition (B), and the content of pentaerythritol (B-1) is not more than the above upper limit, so that molded articles and optical components can be obtained that have an improved performance balance between moist heat resistance and transparency, even in thick-walled molded articles. Here, 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 undergone the esterification reaction.
[0050] In the fatty acid ester composition (B) of this embodiment, the fatty acid constituting the pentaerythritol fatty acid ester (B-2) preferably contains a fatty acid having from 12 to 18 carbon atoms, more preferably a fatty acid having from 14 to 18 carbon atoms, even more preferably a fatty acid having from 16 to 18 carbon atoms, and even more preferably a fatty acid having 18 carbon atoms. This makes it possible to obtain molded articles and optical components with an improved balance of moist heat resistance and transparency, and further reduces mold contamination during molding of the molded articles and optical components.
[0051] In the fatty acid ester composition (B) of this embodiment, 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.)
[0052] Furthermore, 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.
[0053] Examples of such fatty acid esters (B-2) include one or more selected from the group consisting of pentaerythritol laurate, pentaerythritol myristate, pentaerythritol palmitate, pentaerythritol stearate, etc. Among these, pentaerythritol stearate is preferred from the viewpoint of obtaining molded articles and optical components with an improved balance of 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.
[0054] When the fatty acid ester (B-2) contains two 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% by mass or more and 50% by mass or less, more preferably 15% by mass or more and 45% by mass or less, and even more preferably 20% by mass or more and 40% by mass or less, based on the total amount of the fatty acid ester (B-2) being 100% by mass, from the viewpoint of obtaining molded articles and optical components with an improved balance of moist heat resistance and transparency. Furthermore, when the fatty acid ester (B-2) contains two or more selected from the group consisting of monoesters, diesters, triesters, and tetraesters, 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.
[0055] 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, relative to 100 parts by mass of the content of the cyclic olefin copolymer (A). By ensuring that the content of the fatty acid ester composition (B) is equal to or more than the above lower limit, it is possible to obtain molded articles and optical components with an improved balance of 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, based on 100 parts by mass of the content of the cyclic olefin copolymer (A). By keeping the content of the fatty acid ester composition (B) at the above upper limit or less, the amount of gasification of the fatty acid ester composition (B) during molding can be suppressed, and the occurrence of cloudiness can be suppressed. Furthermore, from the viewpoint of obtaining molded articles and optical components with an improved balance of moist heat resistance and transparency, 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, relative to 100 parts by mass of the cyclic olefin copolymer (A).
[0056] 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. When the total content of the cyclic olefin copolymer (A) and the fatty acid ester composition (B) is equal to or more than the above lower limit, the performance balance between moist heat resistance and transparency of molded articles and optical components using the resin composition of this embodiment can be further improved. 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 this embodiment is not particularly limited, but is, for example, 100% by mass or less. Furthermore, from the viewpoint of further improving the performance balance between moist heat resistance and transparency of molded articles and optical components using the resin composition of this embodiment, 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 and 100% by mass or less, more preferably 80% by mass or more and 100% by mass or less, even more preferably 85% by mass or more and 100% by mass or less, even more preferably 90% by mass or more and 100% by mass or less, even more preferably 95% by mass or more and 100% by mass or less, and even more preferably 98% by mass or more and 100% by mass or less, when the total solid content of the resin composition is taken as 100% by mass.
[0057] [Fatty acid metal salts (C)] The resin composition of the present embodiment preferably further contains a fatty acid metal salt (C). By further including a fatty acid metal salt (C) in the resin composition of this embodiment, the 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.
[0058] The fatty acid metal salt (C) of this embodiment preferably contains a metal salt of a long-chain fatty acid having 12 or more carbon atoms, from the viewpoint of further improving the balance of processability and releasability. From the viewpoint of further improving the performance balance between the processability and releasability of the resulting resin composition, the metal salt of a long-chain fatty acid having 12 or more carbon atoms preferably includes one or more selected from the group consisting of 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 stearate, and zinc naphthenate; from the viewpoint of further improving the performance balance between the processability and releasability of the resulting resin composition and the transparency of a molded article using the resin composition, the metal salt preferably includes one or more selected from the group consisting of calcium stearate and zinc stearate, and even more preferably includes zinc stearate.
[0059] From the viewpoint of further improving the performance balance between processability and releasability of the resulting resin composition, the lower limit of the content of fatty acid metal salt (C) in the resin composition of this embodiment is preferably 0.0001 parts by mass or more, more preferably 0.0005 parts by mass or more, even more preferably 0.0010 parts by mass or more, even more preferably 0.0015 parts by mass or more, even more preferably 0.0020 parts by mass or more, even more preferably 0.0025 parts by mass or more, even more preferably 0.0030 parts by mass or more, and even more preferably 0.0035 parts by mass or more, relative to 100 parts by mass of the cyclic olefin copolymer (A). Furthermore, from the viewpoint of further improving the transparency of molded articles using the resin composition, the upper limit of the content of fatty acid metal salt (C) in the resin composition of this embodiment is, when the content of 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. Furthermore, in the resin composition of this embodiment, the content of the fatty acid metal salt (C) is preferably 0.0001 to 0.50 parts by mass, more preferably 0.0001 to 0.40 parts by mass, even more preferably 0.0005 to 0.30 parts by mass, even more preferably 0.0010 to 0.20 parts by mass, even more preferably 0.0015 to 0.15 parts by mass, even more preferably 0.0020 to 0.12 parts by mass, even more preferably 0.0025 to 0.10 parts by mass, even more preferably 0.0030 to 0.07 parts by mass, and even more preferably 0.0035 to 0.05 parts by mass, relative to 100 parts by mass of the cyclic olefin copolymer (A). The fatty acid metal salt (C) of this embodiment may be contained in a 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 formed from a resin composition containing the cyclic olefin copolymer (A) and the fatty acid ester composition (B). Furthermore, when the resin composition of this embodiment contains a hindered amine compound (D) described below, the fatty acid metal salt (C) of this embodiment may be contained in a 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 formed from a resin composition containing the cyclic olefin copolymer (A), the fatty acid ester composition (B), and the hindered amine compound (D).
[0060] [Hindered amine compounds (D)] The resin composition of the present embodiment preferably further contains a hindered amine compound (D). When the resin composition of the present embodiment further contains a hindered amine compound (D), the light resistance of the resulting resin composition can be improved, and deterioration and discoloration due to UV light can be suppressed.
[0061] 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.
[0062] The above proportion 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 identical to the proportion of carbon atoms measured using a CHN elemental analyzer (e.g., CHNS-932 manufactured by LECO).
[0063] 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.
[0064] The above molecular weight of the hindered amine compound (D) is a theoretical value calculated from the chemical formula, and this theoretical value is almost identical to the polystyrene-equivalent weight average molecular weight measured by gel permeation chromatography (GPC) or the molecular weight measured by mass spectrometry.
[0065] Examples of the hindered amine compound (D) that satisfies the above properties include compounds represented by the following chemical formulas [1] to
[37] .
[0066] [ka]
[0067] [ka]
[0068] [ka]
[0069] [ka]
[0070] [ka]
[0071] [ka]
[0072] [ka]
[0073] [ka]
[0074] [ka]
[0075] [ka]
[0076] [ka]
[0077] [ka]
[0078] 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.
[0079] Examples of the hindered amine compound (D) that satisfies the above hexane solubility include compounds represented by the above chemical formulas [1] to
[37] .
[0080] The 5% thermal weight loss temperature of the hindered amine compound (D) when heated at a rate of 5°C / min in nitrogen 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.
[0081] The thermal weight loss temperature can be measured, for example, by a TG / DTA (Thermogravimetry / Differential Thermal Analysis) simultaneous measurement device (for example, DTG-60A / 60AH manufactured by Shimadzu Corporation).
[0082] The hindered amine compound (D) of the present embodiment preferably includes a hindered amine compound represented by the following general formula (1).
[0083] [ka]
[0084] In the general formula (1), n represents 1 or 2. R 1 , R 2 R may be the same or different and represent a hydrogen atom or a methyl group, preferably a methyl group. 1 , R 2 By using a methyl group, coloration of the molded body at high temperatures and in the presence of acidic substances can be prevented.
[0085] R 3 , R 4 and R 5 may be the same or different, and examples thereof include the following (1) to (5). (1) Hydrogen atom (2) Alkyl groups with 1 to 24 carbon atoms (3) An alicyclic skeleton-containing saturated hydrocarbon group that contains an alicyclic skeleton having 5 to 12 carbon atoms, and the alicyclic skeleton may have 1 to 3 alkyl substituents having 1 to 4 carbon atoms. (4)-R A -Ph(-R B )p(where R A is an alkylene group having 1 to 3 carbon atoms, Ph is R B and p is an integer of 0 to 3. (5) A substituted alkyl group having 2 to 4 carbon atoms and at least one substituent selected from an OH group, an alkoxy group having 1 to 8 carbon atoms, and a dialkylamino group (wherein multiple alkyl groups may be the same or different and are alkyl groups having 1 to 4 carbon atoms) on a carbon atom other than the carbon atom directly bonded to the nitrogen atom.
[0086] In the above (3), 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.
[0087] R 3 , R 4 and R 5 R may be the same or different, but preferably (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. 3 , R 4 and R 5 By using such a group as the aryl group, the transmittance at short wavelengths becomes good, and the compound can be suitably used particularly for optical components.
[0088] R 6 represents an alkylene group having 1 to 4 carbon atoms or a single bond.
[0089] R 7 may be the same or different, and examples thereof include the following (1) to (7). (1) Hydrogen atom (2) an aliphatic saturated hydrocarbon group having 1 to 17 carbon atoms (3) An alicyclic skeleton-containing saturated hydrocarbon group that contains an alicyclic skeleton having 5 to 12 carbon atoms, and the alicyclic skeleton may have 1 to 3 alkyl substituents having 1 to 4 carbon atoms. (4)-R 7A -Ph(-R 7B )p (where R 7A represents a divalent or trivalent saturated hydrocarbon group having 1 to 3 carbon atoms, and Ph represents R7B and p is an integer of 0 to 3. (5)-N(R 7F )(R 7G ) (where R 7F , R 7G are each independently an N,N-dialkylamino group represented by an alkyl group having 1 to 18 carbon atoms), or -N(R 7F )- (wherein, R 7F represents an alkyl group having 1 to 18 carbon atoms, and - represents a bond. (6) An aliphatic saturated hydrocarbon group having 2 to 4 carbon atoms, and at least one substituent selected from an OH group, an alkoxy group having 1 to 8 carbon atoms, and a dialkylamino group (wherein multiple alkyl groups may be the same or different and are alkyl groups having 1 to 4 carbon atoms) is present in R 6 a substituted aliphatic saturated hydrocarbon group on a carbon atom other than the carbon atom directly bonded to (7) A group represented by the following formula:
[0090] [ka]
[0091] (R 8 indicates a hydrogen atom or a methyl group, and * indicates a bond.)
[0092] In the above (2), the aliphatic saturated hydrocarbon group having 1 to 17 carbon atoms means a hydrogen atom or an alkyl group having 1 to 17 carbon atoms when n=1, and means an alkylene group having 1 to 17 carbon atoms when n=2. In addition, in the above (3), the alicyclic skeleton-containing saturated hydrocarbon group is a monovalent group when n = 1, and a divalent group when n = 2. Examples of monovalent groups include a cyclohexyl group, and examples of divalent groups include 1,2-cyclohexylene, 1,3-cyclohexylene, and 1,4-cyclohexylene. Furthermore, in the substituted aliphatic saturated hydrocarbon group (6), R6 is a single bond, a carbon atom other than the carbon atom directly bonded to the nitrogen atom has a substituent.
[0093] R in the above general formula (1) 7 When n=1, preferably, (1) a hydrogen atom, (2) an alkyl group having 1 to 17 carbon atoms, (3) an unsubstituted cycloalkyl group having 5 to 12 carbon atoms and 1 to 3 alkyl groups having 1 to 4 carbon atoms, or (5) —N(R 7F )(R 7G ) (where R 7F , R 7G (wherein n is independently an alkyl group having 1 to 18 carbon atoms), an N,N-dialkylamino group represented by (7), and a group represented by the above formula can be used. On the other hand, when n=2, R 7 (2) an alkylene group having 1 to 17 carbon atoms, (3) an unsubstituted or cycloalkylene group having 5 to 12 carbon atoms and 1 to 3 alkyl groups having 1 to 4 carbon atoms, and (5) -N(R 7F )- (wherein, R 7F A group represented by the formula (wherein , represents an alkyl group having 1 to 18 carbon atoms, and - represents a bond) can be used.
[0094] R 7 By using such a group as the aryl group, the transmittance at short wavelengths becomes good, and the compound can be suitably used particularly for optical components.
[0095] Examples of the hindered amine compound represented by the general formula (1) include the compounds represented by the chemical formulas [4] to
[37] above.
[0096] Furthermore, the hindered amine compound represented by the general formula (1) may be a hindered amine compound represented by the following general formula (2): By using this hindered amine compound, coloration of the molded body at high temperatures can be suppressed.
[0097] [ka]
[0098] [In formula (2), a and b are 0 or 1, and a+b=1 is satisfied.] R represents an alkyl group having 1 to 24 carbon atoms. Y is represented by the following general formula:
[0099] [ka]
[0100] (wherein X represents a hydrogen atom or a methyl group, R represents an alkyl group having 1 to 24 carbon atoms, and * represents a bond). Q is represented by the following general formula:
[0101] [ka]
[0102] (wherein m is 0 or 1, and X and Y are the same as above. When m=0, R represents an alkyl group having 1 to 24 carbon atoms, and when m=1, R represents an alkylene group having 1 to 24 carbon atoms. * represents a bond.) A plurality of X, Y, and R may be the same or different from each other.
[0103] Examples of the hindered amine compound represented by the general formula (2) include the compounds represented by the chemical formulas
[12] to
[37] .
[0104] The content of the hindered amine compound (D) in the resin composition of the present 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, relative to 100 parts by mass of the cyclic olefin copolymer (A), from the viewpoint of improving the light resistance of the resulting resin composition.
[0105] The hindered amine compound (D) can be produced by appropriately selecting the conditions according to the methods described in, for example, JP-A Nos. 52-73886, 63-286448, 5-9356, and 5-43745.
[0106] [Other ingredients] In addition to the cyclic olefin copolymer (A) and the fatty acid ester composition (B), the resin composition of this embodiment may contain known additives as optional components within a range that does not impair the good physical properties of the resin composition of this embodiment. Examples of the additives include antioxidants, secondary antioxidants, lubricants, release agents, anti-fogging agents, weather stabilizers, light stabilizers, ultraviolet absorbers, and metal deactivators.
[0107] In the resin composition of this embodiment, the upper limit of the internal haze measured by the following (method) is preferably 0.4% or less, more preferably 0.3% or less. When the internal haze is the upper limit or less, the molded article and optical component using the resin composition of this embodiment can have a more improved balance of moist heat resistance and transparency. The lower limit of the internal haze is not particularly limited, but may be, for example, 0.0% or more, or 0.1% or more. Furthermore, in the resin composition of this embodiment, 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 between moist heat resistance and transparency in a molded article and an optical component using the resin composition of this embodiment.
[0108] (method) 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 with an optical surface measuring 35 mm x 65 mm x 10 mm thick. The internal haze of the injection-molded test piece is measured using benzyl alcohol with a haze meter according to JIS K7136:2000.
[0109] 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; or a method of adding a solution of the cyclic olefin copolymer (A) and the fatty acid ester composition (B) to a poor solvent to cause precipitation.
[0110] In the resin composition of the present embodiment, the method for 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 they 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. Alternatively, 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. Alternatively, 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.
[0111] <Molded bodies and optical components> Next, the molded body of this embodiment will be described. 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.
[0112] The molded article of this embodiment can be suitably used as an optical component in an optical system that requires highly accurate image identification. Optical components are components used in optical devices, etc., and specific examples include lenses for various sensors, pickup lenses, projector lenses, prisms, fθ lenses, imaging lenses, light guide plates, and lenses for head-mounted displays. From the viewpoint of the effects of this embodiment, the molded article can be suitably used as an fθ lens, imaging lens, sensor lens, prism, or light guide plate.
[0113] The method for molding the resin composition of this embodiment to obtain a molded article 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 intended use or molding method. For example, the resin temperature in injection molding is appropriately selected, for example, from the range of usually 150°C to 400°C, preferably 200°C to 350°C, and more preferably 230°C to 330°C.
[0114] Although the embodiments of the present invention have been described above, these are merely examples of the present invention, and various other configurations can also be adopted. Furthermore, the present invention is not limited to the above-described embodiment, and modifications and improvements within the scope of achieving the object of the present invention are included in the present invention. [Example]
[0115] The present invention will be explained in more detail below with reference to examples, but the present invention is not limited to these examples in any way.
[0116] [Example 1] <Polymerization of Cyclic Olefin Copolymer (A)> (Catalyst Preparation) Ethyl aluminum sesquichloride (Al(C2H5) 1.5C l1.5 ) was diluted with cyclohexane as a solvent to prepare an organoaluminum compound catalyst solution.
[0117] (polymerization) Using a stirred polymerization reactor, ethylene and tetracyclo[4.4.0.1 2,5 .1 7,10 The copolymerization reaction of ethylene with 3-dodecene was continuously carried out to obtain a copolymer solution. The organoaluminum compound catalyst solution prepared in the above (Catalyst Preparation) was used as the catalyst, and ethylene was supplied to the polymerization reactor together with hydrogen gas.
[0118] (decalcification) Water and an aqueous solution of sodium hydroxide were added to the resulting copolymer solution to terminate the polymerization reaction and remove the catalyst residues present in the copolymer solution (decalcification). Pentaerythrityl-tetrakis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate] was added as a stabilizer to the decalcified copolymer solution, and the mixture was mixed in a stirring tank for 1 hour.
[0119] (Desolvation) The stabilizer was added to the mixed solution, which was then heated to 180°C to remove the solvent and unreacted monomers, to obtain a molten cyclic olefin copolymer (A) (ethylene and tetracyclo[4.4.0.1 2,5 .1 7,10 ]-3-dodecene) was obtained. 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)) is 62 mol %, and the content of tetracyclo[4.4.0.1 2,5 .1 7,10 The content of repeating units derived from ]-3-dodecene (repeating units (b)) was 38 mol %.
[0120] At this time, the repeating unit (repeating unit (a)) derived from ethylene constituting the cyclic olefin copolymer (A) and the tetracyclo[4.4.0.1 2,5 .1 7,10The content of repeating units derived from ]-3-dodecene (repeating units (b)) was measured using a nuclear magnetic resonance spectrometer "ECA500" manufactured by JEOL Ltd. under the following conditions. Solvent: deuterated tetrachloroethane Sample concentration: 50~100g / L-solvent Pulse repetition time: 5.5 seconds Accumulation times: 6000 to 16000 times Measurement temperature: 120℃ Measured under the above conditions 13 The C-NMR spectrum revealed that the repeating units (repeating units (a)) derived from ethylene and tetracyclo[4.4.0.1 2,5 .1 7,10 The content of repeating units derived from ]-3-dodecene (repeating units (b)) was quantified.
[0121] <Synthesis of hindered amine compounds> The hindered amine compound (D-1) represented by the chemical formula
[35] (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 synthesized by the following method.
[0122] [ka]
[0123] (1) Synthesis of N-dodecyl-2,2,6,6-tetramethylpiperidin-4-amine (TADA) 77.6 g (0.5 mol) of 2,2,6,6-tetramethyl-4-piperidone (TAA), 97.3 g (0.525 mol) of dodecylamine, and 2.3 g of 2% platinum on carbon (50% water content) were charged into 77.6 g of methanol, and the reaction was carried out at a hydrogen pressure of 0.3 MPa and 50°C for 2.5 hours. After filtering off the catalyst, the solvent was removed and the mixture was distilled, yielding 144.4 g of TADA as a yellowish liquid (yield 89%).
[0124] (2) Synthesis of N,N',N"-tridodecyl-N,N',N"-tris-(2,2,6,6-tetramethyl-4-piperidinyl)-[1,3,5]-triazine-2,4,6-triamine (TTADA) 194.8 g (0.6 mol) of TADA synthesized in (1) above and 27.5 g (0.66 mol) of 96% sodium hydroxide were added to 115 g of water, and the mixture was heated to 60 °C. 55.3 g (0.3 mol) of cyanuric chloride dissolved in 210 g of toluene was added dropwise over 1 hour, and the mixture was aged for 3 hours. The mixture was separated and washed twice with water to obtain a toluene solution of the reaction product. The toluene was then distilled off from the toluene solution of the reaction product, and 274 g of dimethylacetamide (DMAc) and 21.8 g (0.16 mol) of potassium carbonate were added. After the addition, the mixture was heated to 150 °C, and 97.4 g (0.3 mol) of TADA dissolved in 97.4 g of DMAc was added dropwise over 2 hours. The mixture was then aged under reflux for 18 hours. After cooling the reaction mass, it was poured into water containing 3.8 g (0.09 mol) of 96% aqueous sodium hydroxide, and the reaction product was extracted with toluene, followed by washing twice with water to obtain a toluene solution of TTADA.
[0125] (3) Synthesis of N,N',N"-tridodecyl-N,N',N"-tris-(1,2,2,6,6-pentamethyl-4-piperidin-4-yl)-[1,3,5]-triazine-2,4,6-triamine (T12M) 35.1 g (1.17 mol) of paraformaldehyde was added to the toluene solution of TTADA synthesized in (2) above, and the temperature was then raised to 80°C. After the temperature was raised, 49.7 g (1.08 mol) of formic acid was added dropwise over 1 hour, and the mixture was then aged for 3 hours. After cooling the reaction mass, it was washed with 125 g of water containing 7.9 g (0.19 mol) of 96% sodium hydroxide, and then washed twice with water. The resulting toluene solution was purified by silica gel column chromatography and concentrated to obtain 291.3 g of T12M as a viscous solution. (Yield 89% / TCTA)
[0126] <Production of Resin Composition> (Extrusion) 100 parts by mass of the cyclic olefin copolymer (A) and 2.3 parts by mass of a fatty acid ester composition (Ba) (content of pentaerythritol (B-1) in fatty acid ester composition (Ba): 0.5% by mass) consisting of pentaerythritol (B-1) and a fatty acid ester of pentaerythritol (a mixture of 32% by mass of pentaerythritol monostearate, 45% by mass of pentaerythritol distearate, and 23% by mass of pentaerythritol tristearate) (B-2) were kneaded and pelletized. The resulting pellets were dried with hot air at a temperature of 100°C for 4 hours to obtain a resin composition. The glass transition temperature (Tg) of the resin composition was 137°C.
[0127] [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 (a mixture of 32% by mass of pentaerythritol monostearate, 45% by mass of pentaerythritol distearate, and 23% by mass of pentaerythritol tristearate) (B-2). The glass transition temperature (Tg) of the resin composition was 137°C.
[0128] [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): 2.5% by mass) consisting of pentaerythritol (B-1) and a fatty acid ester of pentaerythritol (a mixture of 32% by mass of pentaerythritol monostearate, 45% by mass of pentaerythritol distearate, and 23% by mass of pentaerythritol tristearate) (B-2). The glass transition temperature (Tg) of the resin composition was 137°C.
[0129] [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 (a mixture of 32% by mass of pentaerythritol monostearate, 45% by mass of pentaerythritol distearate, and 23% by mass of pentaerythritol tristearate) (B-2). The glass transition temperature (Tg) of the resin composition was 137°C.
[0130] [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.
[0131] [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.
[0132] [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 process. The glass transition temperature (Tg) of the resin composition was 135°C.
[0133] [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 process. The glass transition temperature (Tg) of the resin composition was 136°C.
[0134] [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.
[0135] [Comparative 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.
[0136] Comparative 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 (Bc) (content of pentaerythritol (B-1): 5.5% by mass) consisting of pentaerythritol (B-1) and a fatty acid ester of pentaerythritol (a mixture of 32% by mass of pentaerythritol monostearate, 45% by mass of pentaerythritol distearate, and 23% by mass of pentaerythritol tristearate) (B-2). The glass transition temperature (Tg) of the resin composition was 137°C.
[0137] Comparative 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 (Bf) (content of pentaerythritol (B-1): 10.5 mass%) consisting of pentaerythritol (B-1) and a fatty acid ester of pentaerythritol (a mixture of 32 mass% pentaerythritol monostearate, 45 mass% pentaerythritol distearate, and 23 mass% pentaerythritol tristearate) (B-2). The glass transition temperature (Tg) of the resin composition was 137°C.
[0138] [Example 3] The decalcified copolymer solution obtained in the same manner as in Example 1 was continuously hydrogenated using a nickel / diatomaceous earth catalyst (N112 manufactured by Nikki Chemical Industry Co., Ltd.) under the conditions of a reaction temperature of 100°C, a reaction pressure of 1 MPa, and an LHSV of 5 / hr. To the hydrogenated copolymer solution, pentaerythrityl-tetrakis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate] was added as a stabilizer in an amount of 0.4% by mass relative to the total copolymer solution, and the mixture was mixed in a stirring tank for 1 hour. The solvent was then removed in the same manner as in Example 1, yielding a hydrogenated cyclic olefin copolymer (Aa).
[0139] (Extrusion) 100 parts by mass of the obtained hydrogenated cyclic olefin copolymer (Aa) and 2.0 parts by mass of a fatty acid ester composition (Ba) consisting of pentaerythritol (B-1) and a pentaerythritol fatty acid ester (B-2) (a mixture of 32% by mass of pentaerythritol monostearate, 45% by mass of pentaerythritol distearate, and 23% by mass of pentaerythritol tristearate) (content of pentaerythritol (B-1) in the fatty acid ester composition (Ba): 0.5% by mass) were kneaded and pelletized. The obtained pellets were dried with hot air at a temperature of 100°C for 4 hours to obtain a resin composition. The glass transition temperature (Tg) of the resin composition was 139°C.
[0140] [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): 1.5% by mass) consisting of pentaerythritol (B-1) and a fatty acid ester of pentaerythritol (a mixture of 32% by mass of pentaerythritol monostearate, 45% by mass of pentaerythritol distearate, and 23% by mass of pentaerythritol tristearate) (B-2). The glass transition temperature (Tg) of the resin composition was 139°C.
[0141] [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): 2.5% by mass) consisting of pentaerythritol (B-1) and a fatty acid ester of pentaerythritol (a mixture of 32% by mass of pentaerythritol monostearate, 45% by mass of pentaerythritol distearate, and 23% by mass of pentaerythritol tristearate) (B-2). The glass transition temperature (Tg) of the resin composition was 139°C.
[0142] [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 (a mixture of 32% by mass of pentaerythritol monostearate, 45% by mass of pentaerythritol distearate, and 23% by mass of pentaerythritol tristearate) (B-2). The glass transition temperature (Tg) of the resin composition was 139°C.
[0143] [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.
[0144] [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.
[0145] [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.
[0146] [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 process. The glass transition temperature (Tg) of the resin composition was 138°C.
[0147] [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.
[0148] Comparative 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.
[0149] Comparative 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 (Bc) (content of pentaerythritol (B-1): 5.5% by mass) consisting of pentaerythritol (B-1) and a fatty acid ester of pentaerythritol (a mixture of 32% by mass of pentaerythritol monostearate, 45% by mass of pentaerythritol distearate, and 23% by mass of pentaerythritol tristearate) (B-2). The glass transition temperature (Tg) of the resin composition was 139°C.
[0150] Comparative Example 6 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): 10.5% by mass) consisting of pentaerythritol (B-1) and a fatty acid ester of pentaerythritol (a mixture of 32% by mass of pentaerythritol monostearate, 45% by mass of pentaerythritol distearate, and 23% by mass of pentaerythritol tristearate) (B-2). The glass transition temperature (Tg) of the resin composition was 139°C.
[0151] <Method for evaluating resin composition> (glass transition temperature) 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 at that temperature for 5 minutes. The temperature was then lowered to -20°C at a heating rate of 10°C / min and then held at that temperature for 5 minutes. The glass transition temperature (Tg) of the resin composition was then determined from the endothermic curve obtained when the temperature was raised to 200°C at a heating rate of 10°C / min.
[0152] <Method for producing and evaluating molded products> (Production of molded body) For the resin compositions obtained in Examples 1 to 6 and Comparative Examples 1 to 3, 3 mm thick rectangular plates were produced by the method described below in (1) Square Plate Molding, and 10 mm thick cylindrical molded bodies were produced by the method described below in (2) Cylinder Molding. For the resin compositions obtained in Examples 7 to 12 and Comparative Examples 4 to 6, 10 mm thick cylindrical molded bodies were produced by the method described below in (2) Cylinder Molding.
[0153] (1) Square plate forming Using an injection molding machine (SE30DUZ manufactured by Sumitomo Heavy Industries, Ltd.), the resin compositions obtained in each example and comparative example were injection molded under conditions of a cylinder temperature of 270°C and a mold temperature of 126°C, to produce test pieces of rectangular plate molded bodies with optical surfaces measuring 35 mm in length, 65 mm in width, and 3 mm or 10 mm in thickness.
[0154] (2) Cylinder molding Using an injection molding machine (SE30DUZ manufactured by Sumitomo Heavy Industries, Ltd.), the resin compositions obtained in each example and comparative example were injection molded under conditions of a cylinder temperature of 270°C and a mold temperature of 135°C, to produce test pieces of cylindrical molded bodies with optical surfaces, each measuring 30 mm in diameter and 10 mm in thickness.
[0155] (internal haze) The internal haze of each test piece of the rectangular plate molded body and cylindrical molded body was measured using benzyl alcohol with a haze meter in accordance with JIS K7136: 2000. The results are shown in Tables 1 and 2.
[0156] (visual evaluation) The transparency of each test piece of the square plate molded body and cylindrical molded body was visually evaluated using an optical microscope and a focusing lamp. Those that were transparent and showed no cloudiness were rated as transparent (pass), and those that showed cloudiness were rated as cloudy (fail). The results are shown in Tables 1 and 2.
[0157] (Heat and humidity resistance evaluation) Each test piece of the square plate molded body and cylindrical molded body was subjected to a moist heat resistance test by leaving it in an atmosphere at a temperature of 65°C and a relative humidity of 90% for 168 hours. It was then removed and left to stand in an atmosphere at a temperature of 23°C and a relative humidity of 50% for 48 hours. The internal haze of these test pieces was measured using a haze meter according to JIS K7136:2000 using benzyl alcohol. The delta 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 indicator of moist heat resistance, with a delta internal haze of 1.0% or less being considered a pass and one exceeding 1.0% being considered a fail.
[0158] (Release evaluation) The resin compositions obtained in each example and comparative example were injection molded using an injection molding machine (SE30DUZ manufactured by Sumitomo Heavy Industries, Ltd.) under conditions of a cylinder temperature of 270°C and a mold temperature of 126°C to produce test pieces of rectangular plate molded articles with optical surfaces, each measuring 35 mm long x 65 mm wide x 3 mm or 10 mm thick. When the molded article was ejected from the mold after injection molding, it was rated as A if it could be ejected without resistance, and B if there was resistance during ejection.
[0159] (Lightfastness evaluation) The resin compositions obtained in each example and comparative example were injection molded using an injection molding machine (Sumitomo Heavy Industries, Ltd.; SE30DUZ) under conditions of a cylinder temperature of 270°C and a mold temperature of 126°C to produce rectangular plate-shaped test pieces with optical surfaces measuring 35 mm long, 65 mm wide, and 3 or 10 mm thick. The resulting test pieces were subjected to a lightfastness test at 63°C for 500 hours using a UV fade meter (Suga Test Instruments; U48AUHB). The transmittance of the test pieces before and after the lightfastness test was measured using a UV-visible spectrophotometer (Hitachi High-Tech Science Corporation; UH5700). A difference in transmittance (Δtransmittance) at 450 nm before and after the lightfastness test was evaluated as A if it was within -5 points, B if it was between -5 and -10 points, and C if it was greater than -10 points.
[0160] (comprehensive evaluation) As an overall evaluation, a sample that passed both the visual evaluation and the moist heat resistance evaluation was rated as "pass", and a sample that failed at least one of the visual evaluation and the moist heat resistance evaluation was rated as "fail".
[0161] [Table 1]
[0162] [Table 2]
[0163] Molded articles from the resin compositions described in each Example, in which the content of pentaerythritol (B-1) in the fatty acid ester composition (B) was 5.0 mass% or less, exhibited an improved balance of moist heat resistance and transparency compared to molded articles from the resin compositions described in each Comparative Example. Furthermore, 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), exhibited improved mold releasability while maintaining a balance of moist heat resistance and transparency compared to resin compositions that did not contain a fatty acid metal salt (C). Furthermore, Examples 9, 10, and 15 to 18, which further contained a hindered amine compound (D), exhibited improved light resistance compared to resin compositions that did not contain a hindered amine compound (D).
[0164] This application claims priority based on Japanese Patent Application No. 2023-162860, filed September 26, 2023, the disclosure of which is incorporated herein by reference in its entirety.
Claims
1. a cyclic olefin copolymer (A); a fatty acid ester composition (B) comprising pentaerythritol (B-1) and a fatty acid ester of pentaerythritol (B-2); 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 pentaerythritol (B-1) and the pentaerythritol fatty acid ester (B-2) in the fatty acid ester composition (B) is taken as 100 mass%. 【Chemistry 1】 (In the general formula (I), R 300 represents a hydrogen atom or a linear or branched hydrocarbon group having 1 to 29 carbon atoms. 【Chemistry 2】 (In the general formula (II), u is 0 or 1, v is 0 or a positive integer, w is 0 or 1, and R 61 ~R 78 and 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; R 75 ~R 78 may be bonded to each other to form a monocyclic or polycyclic ring.) 【Transformation 3】 (In the general formula (III), x and d are 0 or an integer of 1 or more, y and z are 0, 1 or 2, and R 81 ~R 99 may be the same or different and are a hydrogen atom, a halogen atom, an aliphatic hydrocarbon group which is an alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 3 to 15 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, or an alkoxy group; R 89 and R 90 and a carbon atom to which R 93 or the carbon atom to which R 91 may be bonded directly or via an alkylene group having 1 to 3 carbon atoms, and when y=z=0, R 95 and R 92 or R 95 and R 99 may be bonded to each other to form a monocyclic or polycyclic aromatic ring. 【Chemistry 4】 (In the general formula (IV), R 100 , 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.
2. The resin composition according to claim 1, A resin composition, wherein the content of the pentaerythritol (B-1) in the fatty acid ester composition (B) is 3.0 mass% or less, when the total content of the pentaerythritol (B-1) and the pentaerythritol fatty acid ester (B-2) in the fatty acid ester composition (B) is 100 mass%.
3. The resin composition according to claim 1 or 2, A resin composition in which the fatty acid constituting the pentaerythritol fatty acid ester (B-2) contains a fatty acid having 12 to 18 carbon atoms.
4. The resin composition according to any one of claims 1 to 3, The resin composition, wherein the pentaerythritol fatty acid ester (B-2) contains a compound represented by the following formula (1): RCOOCH 2 C(CH 2 OH) 3 (1) (In the formula (1), R is a saturated hydrocarbon group having 11 to 17 carbon atoms.)
5. The resin composition according to any one of claims 1 to 4, The resin composition, wherein the fatty acid ester of pentaerythritol (B-2) contains pentaerythritol monostearate.
6. The resin composition according to any one of claims 1 to 5, A resin composition in which the content of the fatty acid ester composition (B) is 0.05 parts by mass or more and 5.0 parts by mass or less, relative to 100 parts by mass of the content of the cyclic olefin copolymer (A).
7. The resin composition according to any one of claims 1 to 6, a resin composition in which the total content of the cyclic olefin copolymer (A) and the fatty acid ester composition (B) is 70% by mass or more and 100% by mass or less, when the total solid content of the resin composition is 100% by mass.
8. The resin composition according to any one of claims 1 to 7, The resin composition further comprises a fatty acid metal salt (C).
9. The resin composition according to claim 8, The resin composition, wherein the fatty acid metal salt (C) comprises a metal salt of a long-chain fatty acid having 12 or more carbon atoms.
10. The resin composition according to claim 8 or 9, The resin composition has a content of the fatty acid metal salt (C) of 0.0001 parts by mass or more and 0.50 parts by mass or less per 100 parts by mass of the cyclic olefin copolymer (A).
11. The resin composition according to any one of claims 1 to 10, The resin composition further comprises a hindered amine compound (D).
12. The resin composition according to claim 11, 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 per 100 parts by mass of the cyclic olefin copolymer (A).
13. The resin composition according to any one of claims 1 to 12, When the total of the repeating units constituting the cyclic olefin copolymer (A) is taken as 100 mol %, A resin composition in which the proportion of the repeating unit (a) in the cyclic olefin copolymer (A) is 5 mol % or more and 95 mol % or less.
14. The resin composition according to any one of claims 1 to 13, A resin composition in which the repeating unit (a) in the cyclic olefin copolymer (A) contains a repeating unit derived from ethylene.
15. The resin composition according to any one of claims 1 to 14, When the total of the repeating units constituting the cyclic olefin copolymer (A) is taken as 100 mol %, A resin composition in which the proportion of the repeating unit (b) in the cyclic olefin copolymer (A) is 5 mol % or more and 95 mol % or less.
16. The resin composition according to any one of claims 1 to 15, A resin composition, wherein the repeating unit (b) in the cyclic olefin copolymer (A) contains a repeating unit (AA) represented by the general formula (II).
17. The resin composition according to any one of claims 1 to 16, The repeating unit (b) in the cyclic olefin copolymer (A) is a bicyclo[2.2.1]-2-heptene and tetracyclo[4.4.0.1]-heptene. 2,5 .1 7,10 ]-3-dodecene.
18. The resin composition according to any one of claims 1 to 17, The cyclic olefin copolymer (A) is a 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 A resin composition comprising one or more members selected from the group consisting of random copolymers of 1-3-dodecene and benzonorbornadiene.
19. The resin composition according to any one of claims 1 to 18, A resin composition having an internal haze of 0.4% or less as measured by the following method. (method) 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 x 65 mm x 10 mm thick. The internal haze of the injection-molded test piece is measured using benzyl alcohol with a haze meter according to JIS K7136:2000.
20. A molded article comprising the resin composition according to any one of claims 1 to 19.
21. An optical component comprising the molded article according to claim 20.
Citation Information
Patent Citations
Resin composition, pentaerythritol derivative composition, and method for producing the same
JP2010184955A
Polymer composition and molded article made from the same
JP2011052154A
Optical component
JP2019133157A
Cyclic-olefin-based copolymer, cyclic-olefin-based copolymer composition, molded body, and medical container
WO2019107363A1
Thermoplastic norbornene-based resin composition
JP1997241484A