Resin composition and optical components

Abstract

A resin composition containing two or more specified neopentyl tertrol fatty acid ester compounds in a specified ratio, wherein the proportion of volatiles measured under specified conditions is 0.10% by mass or less.

Description

Technical Field

[0001] This invention relates to resin compositions and optical elements, and more particularly to resin compositions and transmissive optical elements used in the manufacture of transmissive optical elements. Prior Technology

[0002] In recent years, the applications of transmissive optical elements formed using resin compositions have tended to expand. Consequently, various studies have been conducted to provide transmissive optical elements exhibiting excellent performance using resin compositions. For example, Patent Document 1 proposes a resin composition that yields a transparent thermoplastic molded article with excellent optical performance and suppressed optical performance degradation under high temperature and humidity conditions. Furthermore, for example, Patent Document 2 proposes an optical resin material that can be molded into an optical component with minimal turbidity and significantly suppressed decrease in light transmittance even under high-output, long-term laser irradiation. Moreover, for example, Patent Document 3 proposes a resin composition with excellent release properties, colorless transparency, and laser resistance.

[0003] Patent Documents Patent Document 1: Japanese Patent Publication No. 2010-184955 Patent Document 2: Japanese Patent Publication No. 2009-209166 Patent Document 3: International Patent Publication No. 2005 / 073321 Summary of the Invention

[0004] However, the aforementioned resin compositions, which have been previously proposed, have room for further improvement in terms of the laser resistance, release properties, and heat resistance of the resulting optical elements.

[0005] Therefore, the present invention aims to provide a resin composition that can achieve a high level of laser resistance, release properties and heat resistance to yellowing of the obtained optical elements.

[0006] Furthermore, the present invention aims to provide optical elements with excellent laser resistance, release properties, and resistance to heat yellowing.

[0007] The inventors have devoted themselves to research in order to achieve the above-mentioned objectives. Then, the inventors made a new discovery that if a resin composition containing "two or more specified fatty acid ester compounds in a specified ratio, and the proportion of volatilization measured under specified conditions is 0.10% by mass or less", it becomes possible to form an optical element with excellent laser resistance, release properties and heat resistance to yellowing, thereby completing the present invention.

[0008] That is, this invention is intended to solve the above-mentioned problems smoothly. [1] The resin composition of the present invention is a resin composition containing an alicyclic polymer, a hindered amine compound and a release agent. The release agent contains two or more fatty acid ester compounds selected from the group consisting of a fatty acid diester of neopentyl tertrol, a fatty acid triester of neopentyl tertrol and a fatty acid tetraester of neopentyl tertrol. The content of one of the two or more fatty acid ester compounds is 50% by mass or more but less than 80% by mass relative to the total content of the release agent. The proportion of the amount of volatilization based on the mass of the resin composition before heating at 260°C for 1 hour is 0.10% by mass or less. If a resin composition is used that contains two or more specified fatty acid ester compounds in a specified ratio, and the proportion of volatile matter is less than 0.10% by mass when the volatile matter is measured under specified conditions, then an optical element with excellent laser resistance, release properties and heat resistance can be formed.

[0009] Furthermore, "content of release agent" refers to the total amount of neopentyl tertrol fatty acid ester compounds (but including unavoidable impurities), and the "content of one of two or more fatty acid ester compounds" relative to the total content of release agent can be measured according to the method described in the examples. Also, the "volatility" of the resin composition can be measured according to the method described in the examples.

[0010] [2] Therefore, the resin composition of the present invention related to [1] is preferably composed of a release agent content of 0.2% by mass or more and 0.8% by mass or less per 100 parts by mass of the aforementioned alicyclic polymer. If the release agent content is within the above range, the laser resistance and release properties of the obtained optical element can be further improved.

[0011] [3] Moreover, the resin composition of the present invention related to [1] or [2] above preferably contains neopentyl tert-ester and neopentyl tert-ester as the release agent. If the release agent of the resin composition contains neopentyl tert-ester and neopentyl tert-ester as the blending component, the laser resistance and heat resistance of the obtained optical element can be further improved.

[0012] [4] Furthermore, the resin composition of the present invention related to any of the above [1] to [3] is preferably such that the content of the fatty acid ester compound with a higher degree of esterification among the two or more fatty acid ester compounds is 50% by mass or more but less than 80% by mass relative to the total content of the release agent. If the content of the fatty acid ester compound with a higher degree of esterification relative to the total content of the release agent is 50% by mass or more but less than 80% by mass, the laser resistance and release properties of the obtained optical element can be further improved.

[0013] [5] Furthermore, this invention aims to successfully solve the aforementioned problems. The optical element of this invention contains an alicyclic polymer, a hindered amine compound, and a release agent. The release agent is characterized by containing two or more fatty acid ester compounds selected from the group consisting of neopentyl tertrol fatty acid diester, neopentyl tertrol fatty acid triester, and neopentyl tertrol fatty acid tetraester. The content of one of the two or more fatty acid ester compounds is 50% by mass or more but less than 80% by mass relative to the total content of the release agent. The proportion of the volatilization amount based on the mass of the optical element before heating at the point when the optical element is heated at 260°C for 1 hour is 0.10% by mass or less. Such an optical element, which contains two or more specified fatty acid ester compounds at a specified ratio and the proportion of volatilization amount measured under specified conditions is 0.10% by mass or less, exhibits excellent laser resistance, release properties, and resistance to heat yellowing.

[0014] According to the present invention, a resin composition can be provided that can achieve a high level of laser resistance, release properties and heat resistance to yellowing of the obtained optical elements.

[0015] Furthermore, according to the present invention, optical elements with excellent laser resistance, release properties, and resistance to heat yellowing can be provided. Simple Explanation of the Diagram

[0016] Figure 1 is a graph of an example of the weight loss curve of neopentyl tertrol fatty acid esters upon heating. Implementation

[0017] The embodiments of the present invention are described in detail below. For example, the resin composition of the present invention can be suitably used in the manufacture of the optical elements of the present invention. As optical elements, various transmissive optical elements suitable for a wide range of applications can be cited, without particular limitation. Among these, optical elements formed using the resin composition of the present invention are suitable for use in irradiating semiconductor lasers with short oscillation wavelengths (e.g., blue lasers with wavelengths above 350 nm and below 530 nm) and light-emitting diodes (LEDs).

[0018] (Resin composition)

[0019] The resin composition of this invention comprises a polymer with an alicyclic structure, a hindered amine compound, and a release agent. More specifically, the release agent contained in the resin composition of this invention contains two or more fatty acid ester compounds selected from the group consisting of a neopentyl tert-ester, a neopentyl tert-ester, and a neopentyl tert-ester, wherein the content of one of the two or more fatty acid ester compounds is 50% by mass or more but less than 80% by mass relative to the total content of the release agent. Furthermore, the resin composition of this invention, at the time point of heating at 260°C for 1 hour, has a volatilization rate of 0.10% by mass or less based on the mass of the aforementioned resin composition before heating. By using a resin composition that "contains two or more specified fatty acid ester compounds in a specified ratio, and the volatilization rate is measured under specified conditions and is 0.10% by mass or less", optical elements with excellent laser resistance, release properties, and resistance to heat yellowing can be formed.

[0020] <Volatile content of resin components>

[0021] The resin composition of this invention must have a volatile content of 0.10% by mass or less, based on the mass of the resin composition before heating, at the point when the resin composition is heated at 260°C for 1 hour. Furthermore, a volatile content of 0.09% by mass or less is preferred, 0.08% by mass or less is more preferred, and 0.06% by mass or less is even more preferred. In addition, the lower limit of the volatile content is not particularly limited, but may be, for example, 0.005% by mass or more. If the volatile content is below the aforementioned upper limit, the laser resistance of the obtained optical element can be improved. Furthermore, the volatile content of the resin composition can be expected to vary depending on the amount of low molecular weight components that may be incorporated into the resin composition or may unavoidably be mixed into the resin composition. While the specifications of low molecular weight components are not clearly defined, examples such as free fatty acids that may unavoidably accompany fatty acid ester compounds used as release agents can be considered as options.

[0022] <Polymers with Alicyclic Structures>

[0023] The alicyclic polymers used in this invention are polymers with alicyclic structures in the main chain and / or side chains. From the viewpoints of transparency (light transmittance), mechanical strength, heat resistance, etc., polymers with alicyclic structures in the main chain are preferred.

[0024] As alicyclic structures, saturated cyclic hydrocarbon (cycloalkanes) and unsaturated cyclic hydrocarbon (cycloenes) structures can be listed, but from the viewpoints of transparency, mechanical strength, heat resistance, lightfastness, and weather resistance, cycloalkanes are preferred. The number of carbon atoms constituting the alicyclic structure, from the viewpoints of transparency, mechanical strength, heat resistance, and processability, typically ranges from 4 to 30, with 5 to 20 being preferred, and 5 to 15 being relatively preferred. The proportion of repeating units with an alicyclic structure is typically 50% by mass or more, preferably 70% by mass or more, and relatively preferred to be 90% by mass or more, with an upper limit of 100% by mass. A proportion of repeating units with an alicyclic structure within this range is preferred from the viewpoints of transparency, heat resistance, and lightfastness.

[0025] Examples of polymers containing alicyclic structures include: norethene polymers, monocyclic cycloene addition polymers, vinylcycloalkane polymers, cyclic conjugated diene polymers, and their hydrides. Among these, norethene polymers, monocyclic cycloene addition polymers, vinylcycloalkane polymers, and their hydrides are preferred.

[0026] (1) Norbenzene polymers:

[0027] Examples of norepinene polymers include: ring-opening polymers or ring-opening copolymers of norepinene monomers, addition polymers or addition copolymers of norepinene monomers, addition copolymers of norepinene monomers and vinyl compounds, and hydrogenates thereof.

[0028] Specific examples of northoene monomers include: bicyclo[2.2.1]hept-2-ene (commonly known as "northoene"), 5-methylbicyclo[2.2.1]hept-2-ene, 5,5-dimethylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-butylbicyclo[2.2.1]hept-2-ene, 5-hexylbicyclo[2.2.1]hept-2-ene, 5-octylbicyclo[2.2.1]hept-2-ene, 5-octadecylbicyclo[2.2.1]hept-2-ene, and 5-octadecylbicyclo[2.2.1]hept-2-ene. 5-Ethylenebicyclo[2.2.1]hept-2-ene, 5-Methylenebicyclo[2.2.1]hept-2-ene, 5-Vinylbicyclo[2.2.1]hept-2-ene, 5-Propylenebicyclo[2.2.1]hept-2-ene, 5-Methoxycarbonylbicyclo[2.2.1]hept-2-ene, 5-Cyanobylidenebicyclo[2.2.1]hept-2-ene, 5-Methyl-5-methoxycarbonylbicyclo[2.2.1]hept-2-ene, 5 -Ethoxycarbonylbicyclo[2.2.1]hept-2-ene, 5-methyl-5-ethoxycarbonylbicyclo[2.2.1]hept-2-ene, 2-methylpropionic acid bicyclo[2.2.1]hept-5-en ester, 2-methyloctanoic acid bicyclo[2.2.1]hept-5-en ester, bicyclo[2.2.1]hept-2-ene-5,6-dicarboxylic anhydride, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5,6-di(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5-hydroxy Isopropylbicyclo[2.2.1]hept-2-ene, 5,6-dicarboxylic acid-bicyclo[2.2.1]hept-2-ene, bicyclo[2.2.1]hept-2-ene-5,6-dicarboxylic acid imimine, 5-cyclopentylbicyclo[2.2.1]hept-2-ene, 5-cyclohexylbicyclo[2.2.1]hept-2-ene, 5-cyclohexenylbicyclo[2.2.1]hept-2-ene, 5-phenylbicyclo[2.2.1]hept-2-ene, and other norethenes and their derivatives; tricyclic[4.3.1] [2,5.0 1,6]dec-3,7-diene (commonly known as "bicyclopentadiene"), tricyclo[4.3.1 2,5.0 1,6]dec-3-ene, tricyclo[4.4.1 2,5.0 1,6]undec-3,7-diene, tricyclo[4.4.1 2,5.0 1,6]undec-3,8-diene, tricyclo[4.4.1 2,5.0 1,6]undec-3-ene and other bicyclopentadienes and their derivatives; tetracyclo[7.4.1 10,13.0 1,9.0 2,7]tridecyl-2,4,6,11-tetraene (also known as "1,4-methylbridged-1,4,4a,9a-tetrahydrofuran") and its derivatives; tetracyclo[8.4.1 11,14.0 1,10.0 [3,8] Tetradecene-3,5,7,12-tetraene (also known as "1,4-methylbridged-1,4,4a,5,10,10a-hexahydroanthracene") and its derivatives; and other norethene monomers without a norethene ring.

[0029] Furthermore, examples of norethene monomers include: tetracyclo[4.4.1 2,5.1 7,10.0]dodecyl-3-ene (commonly known as "tetracyclododecene"), 8-methyltetracyclo[4.4.1 2,5.1 7,10.0]dodecyl-3-ene, 8-ethyltetracyclo[4.4.1 2,5.1 7,10.0]dodecyl-3-ene, 8-methylenetetracyclo[4.4.1 2,5.1 7,10.0]dodecyl-3-ene, 8-ethylenetetracyclo[4.4.1 2,5.1 7,10.0]dodecyl-3-ene, 8-vinyltetracyclo[4.4.1 2,5.1 7,10.0]dodecyl-3-ene, and 8-propenyltetracyclo[4.4.1 2,5.1 7,10.0]dodecyl-3-ene. [7,10.0] Dodecyl-3-ene, 8-methoxycarbonyltetracyclo[4.4.1 2,5.1 7,10.0] Dodecyl-3-ene, 8-methyl-8-methoxycarbonyltetracyclo[4.4.1 2,5.1 7,10.0] Dodecyl-3-ene, 8-hydroxymethyltetracyclo[4.4.1 2,5.1 7,10.0] Dodecyl-3-ene, 8-carboxytetracyclo[4.4.1 2,5.1 7,10.0] Dodecyl-3-ene, 8-cyclopentyltetracyclo[4.4.1 2,5.1 7,10.0] Dodecyl-3-ene, 8-cyclohexyltetracyclo[4.4.1 2,5.1 7,10.0] Dodecyl-3-ene, 8-cyclohexen ... Tetracyclic dodecenes such as [7,10.0]dodecyl-3-ene and 8-phenyltetracyclic [4.4.1 2,5.1 7,10.0]dodecyl-3-ene and their derivatives; pentacyclic [6.5.1 1,8.1 3,6.0 2,7.0 9,13]pentadecane-3,10-diene and their derivatives; pentacyclic [7.4.1 3,6.1 10,13.0 1,9.0 2,7]pentadecane-4,11-diene and their derivatives; and other noroalkylene monomers with a noroalkyl ring.

[0030] These norethene monomers can be used alone or in combination of two or more. Copolymers can be made by using norethene monomers with other monomers that can copolymerize.

[0031] Other monomers that can copolymerize with norethene monomers include, for example: 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, and 1-tetradecene. α-olefins with 2 to 20 carbon atoms, such as 1-hexadecene, 1-octadecene, and 1-eicosene; cyclobutene, cyclopentene, cyclohexene, 3,4-dimethylcyclopentene, 3-methylcyclohexene, 2-(2-methylbutyl)-1-cyclohexene, cyclooctene, and 3a,5,6,7a-tetrahydro-4,7-methylbridged-1H-indenene; and non-conjugated dienes such as 1,4-hexadiene, 4-methyl-1,4-hexadiene, 5-methyl-1,4-hexadiene, and 1,7-octadiene; etc. These copolymerizable monomers can be used individually or in combination of two or more.

[0032] Ring-opening polymers of norethene monomers can be synthesized using known methods (see, for example, Japanese Patent Publication No. 2009-209166). Furthermore, hydrogenated norethene polymers can be obtained using conventional methods by hydrogenating ring-opening polymers (including ring-opening copolymers) with hydrogen in the presence of a hydrogenation catalyst.

[0033] Addition copolymers of norethene monomers and copolymerizable monomers can be synthesized using known methods (see, for example, Japanese Patent Publication No. 2009-209166). Addition copolymers of norethene monomers and ethylene are representative examples.

[0034] Hydrates of ring-opening (co)polymers of norethene monomers and addition copolymers of norethene monomers with ethylene are preferred as such polymers.

[0035] (2) Monocyclic cycloene addition polymers:

[0036] Monocyclic cycloene addition polymers can be synthesized by addition polymerization of monocyclic cycloene monomers such as cyclobutene, cyclopentene, cyclohexene, 3,4-dimethylcyclopentene, cycloheptene, and cyclooctene, or by addition copolymerization of these monomers with other monomers capable of copolymerization. Examples of monocyclic cycloene addition polymers include addition (co)polymers of alicyclic conjugated diene monomers and other monomers that can be copolymerized with them as needed, wherein the unsaturated bonds of these monomers are partially hydrogenated as required.

[0037] (3) Vinylcycloalkane polymers:

[0038] Examples of vinylcycloalkane polymers include: (co)polymers of vinylcycloalkane and other monomers that can be copolymerized with it as needed; hydrides of the unsaturated bond portion of (co)polymers of vinylcycloene and other monomers that can be copolymerized with it as needed; hydrides of the aromatic ring and olefinic unsaturated bond portion of (co)polymers of aromatic ethylene monomers and other monomers that can be copolymerized with it as needed; etc.

[0039] Examples of vinylcycloalkanes include vinylcyclopentane, 2-methyl-4-vinylcyclopentane, vinylcyclohexane, and vinylcyclooctane. Examples of vinylcycloalkenes include vinylcyclopentene, 2-methyl-4-vinylcyclopentene, and vinylcyclohexene. Examples of aromatic ethylene monomers include styrene, α-methylstyrene, divinylbenzene, vinylnaphthalene, and vinyltoluene.

[0040] Other monomers that can copolymerize with vinylcycloalkanes, vinylcycloalkenes, and aromatic ethylene monomers include, for example: olefins such as ethylene, propylene, 1-butene, 1-pentene, 1-hexene, 3-methyl-1-butene, and 3-methylpentene; non-conjugated dienes such as 1,4-hexadiene, 4-methyl-1,4-hexadiene, 5-methyl-1,4-hexadiene, and 1,7-octadiene; and conjugated dienes such as 1,3-butadiene, isoprene, and 1,3-hexadiene; etc.

[0041] The polymerization of aromatic ethylene monomers, vinylcycloenes, or vinylcycloalkanes can be carried out using any of the well-known methods such as free radical polymerization, anionic polymerization, and cationic polymerization. However, since the molecular weight of the polymer decreases in cationic polymerization and the molecular weight distribution broadens in free radical polymerization, there is a tendency for the mechanical strength of the molded product to decrease. Therefore, anionic polymerization is preferred. The polymerization method can also be any of suspension polymerization, solution polymerization, or bulk polymerization.

[0042] Anionic polymerization can be carried out using known methods (see, for example, Japanese Patent Publication No. 2009-209166).

[0043] Among vinyl cycloalkane polymers, the preferred types are hydrides of homopolymers of aromatic ethylene monomers, hydrides of copolymers of aromatic ethylene monomers and olefins, hydrides of copolymers of aromatic ethylene monomers and conjugated dienes, and hydrides of terpolymers of aromatic ethylene monomers, olefins, and conjugated dienes.

[0044] (4) Cyclic conjugated diene polymers:

[0045] As a cyclic conjugated diene polymer, polymers and their hydrides formed by the 1,2- or 1,4-addition polymerization of cyclic conjugated diene monomers such as cyclopentadiene and cyclohexadiene can be used.

[0046] Polymers containing alicyclic structures may also have polar groups such as hydroxyl, carboxyl, alkoxy, epoxy, glycidyl, oxycarbonyl, carbonyl, amine, ester, and acid anhydride groups.

[0047] For alicyclic polymers containing unsaturated bonds, hydrogenation before reuse is preferable from the perspective of laser resistance, transparency, and heat resistance. The hydrogenation rate of non-conjugated carbon-carbon double bonds in alicyclic polymers is typically above 80%, preferably above 90%, and even more preferably above 99%.

[0048] Hydrogenation (hydrogenation reaction) can be carried out using conventional methods, but the amount of hydrogenation catalyst, reaction temperature, hydrogen partial pressure, reaction time, and reaction solution concentration can be appropriately set within the optimal range depending on the type of polymer being hydrogenated. While the hydrogenation catalyst is not particularly limited, a homogeneous catalyst composed of metal compounds such as nickel and cobalt combined with organoaluminum or organolithium is preferred. Activated carbon, diatomaceous earth, magnesium oxide, etc., can be used as carriers for the hydrogenation catalyst as needed. The amount of hydrogenation catalyst used is typically 0.01 to 50 parts by weight per 100 parts by weight of polymer. The reaction temperature is typically 25 to 300°C. The hydrogen partial pressure is typically 0.5 to 10 MPa. The reaction time is typically 0.5 to 20 hours.

[0049] Hydrogenated alicyclic polymers can be obtained by filtering out the hydrogenation catalyst solution through self-filtration of the hydrogenation reaction solution to remove the solvent. Methods for removing the solvent include coagulation and direct drying. Coagulation involves mixing the polymer solution with a poor solvent to precipitate the polymer. The precipitated small polymer clumps (particles) are then separated from the liquid, and the polymer is heated and dried to remove the solvent. Poor solvents include, for example, alcohols such as ethanol, n-propanol, and isopropanol; ketones such as acetone and methyl ethyl ketone; and polar solvents such as esters such as ethyl acetate and butyl acetate.

[0050] Direct drying involves heating the polymer solution under reduced pressure to remove the solvent. Well-known equipment such as centrifugal thin-film continuous evaporation dryers, surface-scraped heat exchange continuous reactor dryers, and high-viscosity reactor devices can be used. The vacuum level or temperature can be appropriately selected depending on the equipment used.

[0051] The molecular weight of alicyclic polymers, measured using gel permeation chromatography (GPC) with a cyclohexane solution (or toluene solution if the polymer is insoluble), is typically 5,000 to 500,000, preferably 10,000 to 200,000, and more preferably 20,000 to 150,000. A molecular weight average within the aforementioned range is preferable for achieving a high balance between mechanical strength and processability. The molecular weight distribution (Mw / Mn) of alicyclic polymers measured by GPC is typically below 5.0, preferably below 2.5.

[0052] The glass transition temperature (Tg) of polymers containing alicyclic structures is typically 50–300 °C, with 100–200 °C being preferred and 120–180 °C being even more desirable. The glass transition temperature is a value measured using differential scanning calorimetry (DSC).

[0053] Hindered amine compounds

[0054] Hindered amine compounds are components that function as light stabilizers in resin compositions. As hindered amine compounds, compounds containing piperidine rings with substituents bonded to the carbon atom adjacent to the nitrogen atom can be used. Such hindered amine compounds are preferably compounds containing multiple piperidine rings with substituents respectively bonded to two carbon atoms adjacent to the nitrogen atom. Alkyl groups such as methyl and ethyl are preferred as substituents bonded to the carbon atom adjacent to the nitrogen atom. Compounds with methyl groups respectively bonded to two carbon atoms adjacent to the nitrogen atom are even more preferred.

[0055] Hindered amine compounds are additives used to prevent the photo-oxidative degradation of plastics. They are known to possess functions such as free radical scavenging, hydrogen peroxide decomposition, and metal ion scavenging. For example, hindered amine compounds can scavenge free radicals generated by light irradiation, thus deactivating them.

[0056] Examples of hindered amine compounds include: N,N′,N″,N‴-tetra{4,6-bis[butyl-(N-methyl-2,2,6,6-tetramethylpiperidin-4-yl)amino]tris(2,2,6,6-tetramethyl-4-piperidinyl)butylamine, polycondensates of dibutylamine and 1,3,5-tris(2,2,6,6-tetramethyl-4-piperidinyl)butylamine, and poly{[6-(1,1,3,3-tetramethylbutyl)amino-1,3,5-tris(2,2,6,6-tetramethyl-4-piperidinyl)imino]hexamethylene [(2,2,6,6-Tetramethyl-4-piperidinyl)imino]}, 1,6-hexanediamine-N,N′-bis(2,2,6,6-tetramethyl-4-piperidinyl) and α-linoline-2,4,6-trichloro-1,3,5-triazine polycondensates, poly{(6-α-linoline-symmetric α-2,4-diyl)[(2,2,6,6-tetramethyl-4-piperidinyl)imino]hexamethylene[(2,2,6,6-tetramethyl-4-piperidinyl)imino]}, dibutylamine, 2,4,6-trichloro-1,3,5-triazine, N,N′-bis(2,2,6,6-tetramethyl- High-molecular-weight hindered amine compounds with multiple piperidine rings bonded by a tri-skeletal framework, such as polycondensates of 4-piperidinyl)-1,6-hexamethylenediamine and N-(2,2,6,6-tetramethyl-4-piperidinyl)butylamine; crude polymers of dimethyl succinate and 4-hydroxy-2,2,6,6-tetramethyl-1-piperidinol; and mixed esterifications of 1,2,3,4-butanetetracarboxylic acid, 1,2,2,6,6-pentamethyl-4-piperidinol, and 3,9-bis(2-hydroxy-1,1-dimethylethyl)-2,4,8,10-tetraoxospiro[5,5]undecane, etc. High molecular weight hindered amine compounds with bonded structures; low molecular weight hindered amine compounds such as N,N′-bis(2,2,6,6-tetramethyl-4-piperidinyl)-N,N′-dimethoxyhexamethylenediamine, 2-[3,5-bis(tert-butyl)-4-hydroxybenzyl]-2-n-butylmalonate bis(1,2,2,6,6-pentamethyl-4-piperidinyl), sebacate bis(1,2,2,6,6-pentamethyl-4-piperidinyl), sebacate bis(2,2,6,6-tetramethyl-4-piperidinyl), sebacate bis(N-methyl-2,2,6,6-tetramethyl-4-piperidinyl); etc.

[0057] Among these, particularly suitable hindered amine compounds are poly{[6-(1,1,3,3-tetramethylbutyl)amino-1,3,5-tris(2,2,6,6-tetramethyl-4-piperidinyl)imino]hexamethylene[(2,2,6,6-tetramethyl-4-piperidinyl)imino]} and N,N′-bis(2,2,6,6-tetramethyl-4-piperidinyl) Polycondensates of N,N′-dimethylhexamethylenediamine, bis(1,2,2,6,6-pentamethyl-4-piperidinyl) sebacate, dibutylamine, 2,4,6-trichloro-1,3,5-tris(2,2,6,6-tetramethyl-4-piperidinyl)-1,6-hexamethylenediamine, and N-(2,2,6,6-tetramethyl-4-piperidinyl)butylamine, etc.

[0058] The hindered amine compound preferably has a molecular weight of 2,000 or higher and 5,000 or lower. The resin composition of this invention exhibits excellent dispersibility of the hindered amine compound due to the presence of a specific release agent. Furthermore, the molecular weight of the hindered amine compound is measured using a gel permeation chromatography (GPC) system employing tetrahydrofuran as the solvent, and is determined to be the number average molecular weight.

[0059] [Content of hindered amine compounds]

[0060] The content of the hindered amine compound relative to 100 parts by weight of the alicyclic polymer is preferably 0.01 parts by weight or more, more preferably 0.05 parts by weight or more, and preferably 0.2 parts by weight or less, and more preferably 0.15 parts by weight or less. If the content of the hindered amine compound is above or below the aforementioned lower limit, the improvement effect on lightfastness can be fully realized, and coloration can be effectively suppressed in situations such as prolonged outdoor use of optical components. If the content of the hindered amine compound is below the aforementioned upper limit, coloration of the optical component due to the coloring of the hindered amine compound itself can be suppressed. Furthermore, if the content of the hindered amine compound is below the aforementioned upper limit, issues such as partial evaporation and dispersion of the hindered amine compound, decreased dispersibility of the alicyclic polymer, and decreased transparency of the optical component can be effectively suppressed.

[0061] Release agent

[0062] The release agent contains two or more fatty acid ester compounds selected from the group consisting of neopentyl tertrol fatty acid diester, neopentyl tertrol fatty acid triester and neopentyl tertrol fatty acid tetraester. The neopentyl tertrol fatty acid diester, neopentyl tertrol fatty acid triester and neopentyl tertrol fatty acid tetraester are fatty acid ester compounds represented by the following formula (1). (RCOOCH 2) mC(CH 2OH) n...(1) (In the formula, R is a hydrocarbon group with 8 to 26 carbon atoms. m is an integer from 2 to 4. The sum of m and n is 4.)

[0063] In addition, examples of fatty acids used in the synthesis of neopentyl tertrol fatty acid esters include: lauric acid (CH3(CH2)10COOH), myristic acid (CH3(CH2)12COOH), palmitic acid (CH3(CH2)14COOH), stearic acid (CH3(CH2)16COOH), oleic acid (C18H34O2), and carotene acid (CH3(CH2)20COOH). Among these, stearic acid (CH3(CH2)16COOH) is preferred from the viewpoint of volatility and versatility.

[0064] [The blending ratio of compounds in the release agent]

[0065] In the release agent, the content of one of the two or more fatty acid ester compounds (hereinafter sometimes referred to as "fatty acid ester compound A") relative to the total content of the release agent must be 50% by mass or more but not more than 80% by mass, preferably 60% by mass or more, and preferably not more than 72% by mass. If the content of fatty acid ester compound A relative to the total content of the release agent is within the above range, the laser resistance and release properties can be further improved in a balanced manner.

[0066] Therefore, among two or more fatty acid ester compounds, the content of the fatty acid ester compound with a higher degree of esterification relative to the total content of the release agent is preferably 50% by mass or more, more preferably 60% by mass or more, more preferably less than 80% by mass, and more preferably less than 72% by mass. In other words, it is preferable to use fatty acid ester compound A with a higher degree of esterification and have its content within the above range. If the content of the fatty acid ester compound with a higher degree of esterification relative to the total content of the release agent meets the above range, the laser resistance and release properties of the obtained optical element can be further improved.

[0067] Furthermore, among fatty acid ester compounds other than fatty acid ester compound A, the fatty acid ester compound with the highest content is designated as "fatty acid ester compound B". The content of fatty acid ester compound B is preferably 20% by mass or more, preferably 25% by mass or more, preferably less than 50% by mass, and preferably less than 32% by mass.

[0068] Furthermore, the release agent preferably contains both neopentyl tert-ester and neopentyl tert-ester fatty acid. If the release agent, which is an admixture of the resin composition, contains both neopentyl tert-ester and neopentyl tert-ester fatty acid, the light transmittance, laser resistance, and resistance to heat yellowing of the obtained optical element can be further improved. In this case, it is preferable that the neopentyl tert-ester fatty acid is equivalent to "fatty acid ester compound A" as described above, and the neopentyl tert-ester fatty acid is equivalent to "fatty acid ester compound B".

[0069] [Content of release agent]

[0070] Furthermore, the content of the release agent relative to 100 parts by weight of the alicyclic polymer is preferably 0.2% by mass or more, more preferably 0.3% by mass or more, and preferably 0.8% by mass or less, and even more preferably 0.6% by mass or less. If the content of the release agent is above or below the aforementioned lower limit, the release property of the obtained optical element can be improved, and continuous molding of the optical element can be easily performed. Furthermore, if the content of the release agent is below or below the aforementioned upper limit, the light transmittance and laser resistance of the obtained optical element can be improved.

[0071] <Other Ingredients>

[0072] Furthermore, the resin composition of the present invention may also contain other components besides those described above. There are no particular limitations on other components; examples include antioxidants and moisture-resistant agents.

[0073] [Antioxidants]

[0074] Examples of antioxidants include phenolic antioxidants and phosphorus antioxidants (excluding those that qualify as phenolic antioxidants). Among these, hindered phenolic antioxidants are preferred.

[0075] Because the resin composition of the present invention incorporates antioxidants, it can prevent the coloring or strength reduction of the molded article caused by oxidative deterioration during molding. Examples of phenolic antioxidants include: 2-tributyl-6-(3-tributyl-2-hydroxy-5-methylbenzyl)-4-methylphenyl acrylate, 2,4-di(tripentyl)-6-{1-[3,5-di(tripentyl)-2-hydroxyphenyl]ethyl}phenyl acrylate, and other acrylic acid compounds; octadecyl 3-[3,5-di(tributyl)-4-hydroxyphenyl]propionate, 2,2′-methylenebis(4-methyl-6-tributylphenol), 1,1,3-tris(2-methyl-4-hydroxy-5-tributylphenyl)butane, 1,3,5-trimethyl-2,4,6-tris[3,5-di(tributyl)-4-hydroxybenzyl]benzene, and tetra(3′,5′-di(tributyl)-4′-hydroxyphenyl]propionate methane. That is, alkyl-substituted phenolic compounds such as tetrakis(3-[3,5-di(tributyl)-4-hydroxyphenyl]propionate]neopentetrol ester and bis[3-(3-tributyl-4-hydroxy-5-methylphenyl)propionate]triethylene glycol ester; 6-[4-hydroxy-3,5-di(tributyl)anilino]-2,4-bisoctylthio-1,3,5-tris(2,4- ... Tris(2-octylthio-4,6-bis[3,5-di(tributyl)-4-oxyaniline]-1,3,5-tris(2-octylthio-4,6-bis[3,5-di(tributyl)-4-oxyaniline]-1,3,5-tris(2-octylthio-4-{3-[2,4,8,10-tetra(tributyl)diphenyl[d,f][1,3,2]dioxophosphine-6-yloxy]propyl}o-cresol is a hindered phenolic antioxidant with an intramolecular phosphorus atom.

[0076] Examples of phosphorus antioxidants include: triphenyl phosphite, diphenyl phosphite isodecanyl ester, phenyl phosphite diisodecyl ester, nonylphenyl phosphite, dinonylphenyl phosphite, 2,4-di(tributyl)phenyl phosphite, 10-(3,5-di(tributyl)-4-hydroxybenzyl)-9,10-dihydro-9-oxo-10-phosphenanthrene-10-oxide, and other monophosphite compounds; 4,4′-butylidene bis[di(decayl)-3-methyl-6-tributylphenyl phosphite], 4,4′-isopropylidene bis(dialkyl(C12~C15) phenyl phosphite), and other diphosphite compounds. Among these, monophosphite compounds are preferred, and nonylphenyl phosphite, dinonylphenyl phosphite, and 2,4-di(tributyl)phenyl phosphite are particularly preferred. A phenolic structure has at least one hydroxyl group bonded to a benzene ring.

[0077] Hindered phenolic antioxidants are compounds with a group represented by the following formula (1), which can scavenge peroxide free radicals.

[0078] 『Chemical Formula 1』

[0079] In formula (1), R1 and R2 each independently represent a group having 1 or more carbon atoms, and the total number of carbon atoms constituting R1 and R2 is 2 to 20, preferably 3 to 15, and more preferably 5 to 10. * represents an atomic bond. Examples of R1 and R2 include alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, secondary butyl, and tertiary butyl. Further, R1 and R2 may also be those in which a sulfur atom is inserted between the carbon-carbon bonds of these alkyl groups. The number of the groups represented by the aforementioned formula (1) contained in the hindered phenol antioxidant is not particularly limited, and is usually 1 to 10, preferably 1 to 5.

[0080] In addition, the content of the antioxidant is not particularly limited. For example, relative to 100 parts by mass of the alicyclic structure-containing polymer, it is preferably 0.01 part by mass or more, more preferably 0.03 part by mass or more, and preferably 1.0 part by mass or less, more preferably 0.5 part by mass or less.

[0081] [Humidity Resistant Agent]

[0082] As the humidity resistant agent, for example, elastomers such as the main chain hydrogenated product of styrene-butadiene-styrene block copolymer [styrene-ethylene-butene-styrene block copolymer (SEBS)], the main chain hydrogenated product of styrene-isoprene-styrene block copolymer [=styrene-ethylene-propylene-styrene block copolymer (SEPS)] can be added. If such a humidity resistant agent is added, the optical parts are less likely to become cloudy under high temperature and high humidity. The addition amount of the humidity resistant agent relative to 100 parts by mass of the alicyclic structure-containing polymer is preferably 0.05 part by mass or more, more preferably 0.1 part by mass or more, even more preferably 0.15 part by mass or more, and preferably 10 parts by mass or less, more preferably 1 part by mass or less, even more preferably 0.3 part by mass or less.

[0083] [Other Additives]

[0084] Moreover, in the resin composition of the present invention, within the range not impairing the original purpose, other well-known additives such as other mold release agents, flame retardants, antibacterial agents, wood powder, coupling agents, plasticizers, colorants, lubricants, silicone oils, foaming agents, surfactants, fillers, etc. can also be blended.

[0085] <Method for manufacturing resin composition>

[0086] The resin composition of this invention is not particularly limited. For example, it can be manufactured by a method that achieves good mixing of the alicyclic polymer, hindered amine compound, release agent, and various additives that may be added as desired, as described above. Examples of such methods include: mixing the alicyclic polymer in a molten state using a biaxial mixer, or removing the solvent by coagulation, casting, or direct drying after dissolving and mixing in a suitable solvent. Furthermore, the obtained resin composition can also be shaped into granules by any method.

[0087] For mixing, various melt mixing machines can be used, such as single-shaft extruders, twin-shaft extruders, Bamboo mixers, kneaders, rollers, and feeder rudders. The mixing temperature is preferably above 200°C, more preferably above 240°C, and below 400°C, with below 300°C being ideal. Furthermore, during mixing, the components can be mixed all at once, or added in batches while mixing.

[0088] (Optical components)

[0089] The optical element of this invention comprises an alicyclic polymer, a hindered amine compound, and a release agent. The release agent contains two or more fatty acid ester compounds selected from the group consisting of neopentyl tert-ester, neopentyl tert-ester, and neopentyl tert-ester fatty acid esters. The content of one of the two or more fatty acid ester compounds is 50% by mass or more but less than 80% by mass relative to the total content of the release agent. Furthermore, the proportion of volatilization based on the mass of the optical element before heating, at the point when the optical element is heated at 260°C for 1 hour, is 0.10% by mass or less. The optical element of this invention contains two or more specified fatty acid ester compounds at a specified ratio, and the proportion of volatilization measured under specified conditions is 0.10% by mass or less, thus exhibiting excellent laser resistance, release properties, and resistance to heat yellowing.

[0090] The alicyclic polymer, hindered amine compound, release agent, and other arbitrary components contained in the optical element of the present invention can be listed above. Furthermore, the suitable range of the content of one of the two or more fatty acid ester compounds in the optical element, and the suitable range of the proportion of volatilization based on the mass of the optical element before heating at the point when the optical element is heated at 260°C for 1 hour, are the ranges described above as suitable ranges for the resin composition of the present invention.

[0091] Manufacturing Method of Optical Components

[0092] Furthermore, the optical element can be manufactured by molding the resin composition of the present invention into any method suitable for the desired shape. Examples of molding methods include melt extrusion molding, melt casting molding, and injection molding. Molding conditions can be appropriately set according to the desired shape.

[0093] Example

[0094] The following examples and comparative examples further illustrate the present invention in detail. However, the present invention is not limited to these examples. In the examples and comparative examples, various properties and evaluations are performed as described below. Furthermore, the alicyclic polymers used in the examples and comparative examples are synthesized according to the following procedures.

[0095] Glass transition temperature of polymers containing alicyclic structures

[0096] The glass transition temperature (Tg) of alicyclic polymers was measured using a differential scanning calorimeter (SII Nanotechnology, "DSC6220") according to JIS K7121 at a heating rate of 10°C / min.

[0097] <Weight-average molecular weight and molecular weight distribution of polymers containing alicyclic structures>

[0098] The weight-average molecular weight and molecular weight distribution of alicyclic polymers were determined in polystyrene equivalent form by gel permeation chromatography (GPC) using cyclohexane as the precipitate.

[0099] <Volatile Amount of Resin Components and Optical Elements>

[0100] The amount of volatilization of the resin composition at the time point of heating at 260°C for 1 hour was measured as follows. Using a differential thermal gravimetric analyzer (Seiko Instruments, TG / DTA 200), the granulated resin composition obtained in the examples and comparative examples before drying was heated to 260°C under normal pressure and nitrogen gas atmosphere at a heating rate of 10°C / min, and held at 260°C isothermally for 100 minutes. During the 100-minute holding time, the percentage decrease in mass at the 30-minute mark was defined as G30, and the percentage decrease in mass at the 90-minute mark was defined as G90. The amount of volatilization ΔG at the time point of heating at 260°C for 1 hour was calculated accordingly. ΔG (mass%) = G90 - G30

[0101] Figure 1 is a graph illustrating an example of the weight loss upon heating curve of neopentyl tertrol fatty acid esters. The horizontal axis of Figure 1 represents the heating temperature, and the vertical axis represents the weight loss upon heating (mass %). Based on Figure 1, the weight loss upon heating (mass %) at 260°C for each heating time can be accurately measured.

[0102] In addition, the same measurements were performed on the flat resin molded articles manufactured in the embodiments, and it was confirmed that the volatile content was less than 0.10% by mass.

[0103] (Quantitative methods for various fatty acid ester compounds contained in release agents)

[0104] GPC method will be performed under the following conditions. Measurement equipment: HLC-8220GPC (manufactured by Tosoh Corporation) Tubing: G2000HXL + G1000HXL Solvent:THF Flow rate: 1.0 mL / min Column temperature: 40℃ Sample concentration: 0.3% Injection volume: 100 μL Detection sensitivity: 0.100 mV / min Detector: RI Standard material: Polystyrene (manufactured by Tosoh Corporation, Mw=526, 2630, 10200)

[0105] Under the above conditions, GPC measurements are performed, and the content (mass %) of each fatty acid ester compound contained in the release agent is determined based on the area ratio of the graphic. The total mass of unavoidable impurities such as fatty acid monoester, fatty acid diester, fatty acid triester, fatty acid tetraester and free fatty acid is defined as 100% by mass.

[0106] Light transmittance

[0107] Within the two flat resin molded bodies obtained in the Examples and Comparative Examples, the light transmittance at a wavelength of 400 nm and a light path length of 3 mm was measured using a spectrophotometer (manufactured by Japan Spectrophotometer Co., Ltd., "V-570"). The initial value of the light transmittance at a wavelength of 400 nm was defined as T0%. A:More than 90% B: Not reaching 90%

[0108] Laser resistance

[0109] For a flat resin molded body whose light transmittance has been evaluated, a cyan laser with an oscillation wavelength of 405±10 nm was irradiated for 500 hours at an output of 4000 mW / cm² at an environment of 80°C. The degree of decrease in light transmittance at a wavelength of 400 nm before and after irradiation under these conditions was measured. Using the initial value T0% of the light transmittance at a wavelength of 400 nm measured above and the value T1% of the light transmittance at a wavelength of 400 nm after irradiation, the absolute value |ΔT%| of the difference between the two, T1-T0, was calculated and evaluated according to the following criteria. Furthermore, a spectrophotometer (manufactured by Nippon Spectrophotometer Co., Ltd., V-570) was used to measure the light transmittance T1% at a wavelength of 400 nm after irradiation. The smaller the absolute value of the difference between the two, the lower the degree of possible whitening and the better the laser resistance. A: ΔT%≦0.2% B: 0.2% < ΔT% ≦ 0.5% C: 0.5% < ΔT%

[0110] <Deformation>

[0111] The resin composition (granules) used in the manufacture of optical elements in the Examples and Comparative Examples were heated at 80°C for 4 hours and dried. Subsequently, the dried granules were molded into optical elements (lenses; diameter 3.5 mm, R=2.2 mm) using an injection molding apparatus (FANUC product number α-100B). Molding conditions were set as follows: resin temperature 260°C, mold temperature 115°C, and cycle time 1 minute. The amount of resin composition used in each injection was 25 g. The number of injections until the first adhesion of the optical element to the mold occurred was recorded. If adhesion occurred, the test was stopped at this point; even if adhesion did not occur, the test ended at 600 injections. A higher number of injections until adhesion occurred indicated better release properties. Evaluation was conducted according to the following criteria. The results are shown in Table 1. A: More than 500 injections B: 200 or more injections but less than 500 injections C: Unable to form (less than 200 injections)

[0112] <Resistant to heat yellowing>

[0113] Within the two flat resin molded bodies obtained in the Examples and Comparative Examples, the yellow index (YI) was measured in transmission mode with a light path length of 3 mm using a colorimeter (product name "SE-2000", manufactured by Nippon Denshoku Kogyo Co., Ltd.) in accordance with JIS K7373. Furthermore, only the yellow index of air was measured as a blank at this time. Subsequently, after a heat resistance test was conducted by placing the optical element under conditions of 21% by volume and 100°C for 1,000 hours, the yellow index was measured again as described above. The yellowing degree (ΔδYI) was calculated using the following formula and evaluated according to the following criteria. ΔδYI = ΔδYI / (1 - ΔδYI) 0 In formula (I), ΔδYI1 represents the difference between the yellowness of the specimen after the heat resistance test (YI1) and the yellowness of the blank (air) (YIB), and ΔδYI0 represents the difference between the yellowness of the specimen before the heat resistance test (YI0) and the yellowness of the blank (air) (YIB). The smaller ΔδYI is, the less yellowing occurs at high temperatures and the better the heat resistance. A: Not reaching 0.3 B: 0.3 or higher but less than 0.5 C: 0.5 or higher

[0114] (Example 1)

[0115] Synthesis of Polymers Containing Alicyclic Structures

[0116] In a dried, nitrogen-purged stainless steel pressure vessel, 76 parts of styrene and 4 parts of isoprene were sealed and stirred to prepare a mixed monomer. Next, in a dried, nitrogen-purged stainless steel autoclave equipped with an electromagnetic stirrer, 320 parts of dehydrated cyclohexane, 4 parts of the prepared mixed monomer, and 0.1 parts of dibutyl ether were placed. While stirring at 50°C, 0.18 parts of a hexane solution of n-butyllithium (15% concentration) were added to the autoclave to begin polymerization. After 0.5 hours from the start of the reaction (at which point the conversion rate is 96%), 76 parts of the mixed monomer were continuously added to the polymerization reaction solution over a period of 1 hour to continue the polymerization reaction. After another 0.5 hours from the end of the addition (at which point the conversion rate is 95%), 0.1 parts of isopropanol were added to stop the polymerization reaction, yielding a reaction solution containing the styrene-isoprene copolymer. To 400 parts of the obtained reaction solution, 8 parts of stabilizing nickel hydrogenation catalyst E19Z (manufactured by Nichih Chemical Co., Ltd.; nickel-diatomite based hydrogenation catalyst (60% nickel content)) were added, and the solution was placed in a stainless steel autoclave. Hydrogen was supplied to maintain the pressure inside the autoclave at 4.5 MPa by purging the interior with hydrogen gas, and the hydrogenation reaction was carried out at 160°C for 6 hours. Subsequently, the solution was filtered under pressure at 0.25 MPa using a pressure filter (IHI FUNDABAC filter) with a sodium radiolite #800 filter bed to obtain a colorless and transparent solution free of catalyst. This hydrogenation reaction solution was then injected into a mixture of 250 parts acetone and 250 parts isopropanol while stirring to precipitate the hydrides, which were then filtered and recovered. The recovered hydrides were further washed with 200 parts acetone and then dried for 24 hours using a vacuum dryer at 100°C with the pressure reduced to below 1 mmHg. The yield of the hydride was 99%. The weight-average molecular weight (Mw) of this hydride was 91,000, the molecular weight distribution (Mw / Mn) was 1.27, and the Tg was 125°C. The obtained hydride will sometimes be referred to as "HPSt".

[0117] <Manufacturing of Resin Components>

[0118] In 100 parts of the alicyclic polymer (HPSt) obtained above, 0.1 parts of 6-tributyl-4-{3-[2,4,8,10-tetra(tributyl)diphenyl[d,f][1,3,2]dioxan-6-yloxy]propyl}o-cresol (manufactured by Sumitomo Chemical Co., Ltd.; "SUMILIZER GP") as an antioxidant, and dibutylamine, 2,4,6-trichloro-1,3,5-tris(2,2,6,6-tetramethyl-4-piperidinyl)-1,6-hexamethylenediamine, and N-(2,2,6,6-tetramethyl-4-piperidinyl)butylamine (manufactured by BASF Co., Ltd.; "CHIMASSORB (registered trademark) 2020FDL") were mixed in equal amounts. The mixture consisted of 0.1 parts of a neopentyl tert-ester composition of fatty acids (containing 68% by mass of neopentyl tert-tetrastearate and 27% by mass of neopentyl tert-tristearate, with the remainder being unavoidable impurities such as neopentyl tert-esters of fatty acids with lower esterification and free fatty acids) as a release agent. The mixture was then kneaded and extruded using a twin-shaft mixer (Toshiba Machine Co., Ltd., TEM-35B, screw diameter 37 mm, L / D=32, screw speed 250 rpm, resin temperature 230°C, feed rate 10 kg / hour) to obtain a granulated resin composition. The obtained granules were heated at 80°C for 4 hours and then dried.

[0119] Manufacturing of Optical Components

[0120] Using an injection molding apparatus (FANUC, product number α-100B), the dried granules obtained above were injection molded under the conditions of resin temperature 260°C, mold temperature 110°C, and cycle time 1 minute to obtain four 65 mm × 65 mm × 3 mm flat resin molded bodies (optical elements). Various evaluations were performed on the obtained optical elements as described above. The results are shown in Table 1.

[0121] (Example 2)

[0122] Except for the use of a fatty acid neopentyl ester composition containing 69% by mass of tripearic acid neopentyl ester and 25% by mass of distearate neopentyl ester (the residue consists of unavoidable impurities such as neopentyl esters of fatty acids with different degrees of esterification and free fatty acids) as a release agent, the same procedures, measurements, and evaluations as in Example 1 were performed. The results are shown in Table 1.

[0123] (Example 3)

[0124] Except for the use of a fatty acid neopentyl ester composition containing 55% by mass of tetrastearate neopentyl ester and 35% by mass of tripearyl ester (the remainder consists of unavoidable impurities such as neopentyl esters of fatty acids with lower degrees of esterification and free fatty acids) as a release agent, the same procedures, measurements, and evaluations as in Example 1 were performed. The results are shown in Table 1.

[0125] (Example 4)

[0126] Except for the use of a neopentyl ester composition containing 75% by mass of neopentyl tetrastearate and 20% by mass of neopentyl tristearate (the residue consists of unavoidable impurities such as neopentyl esters of fatty acids with lower degrees of esterification and free fatty acids) as a release agent, and the modification of the hindered amine compound used as a light stabilizer to poly{[6-(1,1,3,3-tetramethylbutyl)amino-1,3,5-tris(2,2,6,6-tetramethyl-4-piperidinyl)imino]hexamethylene[(2,2,6,6-tetramethyl-4-piperidinyl)imino]} (manufactured by BASF; "CHIMASSORB (registered trademark) 944 FDL"; molecular weight: 2000~3100; nominal value), the same operations, measurements, and evaluations as in Example 1 were performed. The results are shown in Table 1.

[0127] (Example 5)

[0128] Except for changing the amount of release agent to 0.2 parts by mass, the same operations, measurements, and evaluations as in Example 1 were performed. The results are shown in Table 1.

[0129] (Example 6)

[0130] Except for changing the amount of release agent to 0.8 parts by weight, the same operations, measurements, and evaluations as in Example 1 were performed. The results are shown in Table 1.

[0131] (Example 7)

[0132] Except that HPSt was replaced with an ethylene / TCD copolymer containing an alicyclic polymer synthesized according to the following method, all the same operations, measurements and evaluations were performed as in Example 1. The results are shown in Table 1.

[0133] Synthesis of Polymers Containing Alicyclic Structures

[0134] 235 mL of cyclohexane was introduced into a 500 mL glass autoclave purged with nitrogen, and the liquid and gas phases were saturated with ethylene at a flow rate of 50 L / h. Then, 2 mL of tetracyclo[4.4.1 2,5.1 7,10.0]dodecyl-3-ene (hereinafter referred to as "TCD") and 1.25 mmol of methylaluminoxane (calculated as aluminum atoms) were added to the autoclave. Next, 0.001 mmol of a transition metal catalyst was added using conventional methods to initiate polymerization. The reaction was carried out for 10 minutes at 25 °C and atmospheric pressure under an ethylene atmosphere, and then the polymerization was stopped by adding a small amount of isobutanol. After polymerization, the reactants were placed in a mixed solvent of acetone / methanol (500 mL each) with 5 mL of concentrated hydrochloric acid added, allowing the polymer to precipitate completely. The precipitate was then filtered through a glass filter after stirring. The polymer was dried under reduced pressure at 130 °C for 10 hours to obtain the ethylene / TCD copolymer. The weight-average molecular weight (Mw) and molecular weight distribution (Mw / Mn) of the ethylene / TCD copolymer were measured, and the results showed that Mw was 65,000 and Mw / Mn was 2.15. Its glass transition temperature was 132℃.

[0135] (Comparative Example 1)

[0136] Except for the use of a neopentyl ester composition containing 41% by mass of distearate and 38% by mass of tripearic acid (the remainder consists of unavoidable impurities such as neopentyl esters of fatty acids with different degrees of esterification and free fatty acids) as a release agent, the same procedures, measurements, and evaluations as in Example 1 were performed. The results are shown in Table 1.

[0137] (Comparative Example 2)

[0138] Except for one part by mass of a fatty acid neopentyl tetraethylene ester composition containing more than 90% by mass of tetrastearate (the remaining portion consists of unavoidable impurities such as neopentyl tetraethylene esters of fatty acids with different degrees of esterification and free fatty acids) as a release agent, the same operations, measurements, and evaluations as in Example 1 were performed. The results are shown in Table 1.

[0139] (Comparative Example 3)

[0140] Except for the use of a neopentyl ester composition containing at least 90% by weight of distearate neopentyl ester (the remainder consists of unavoidable impurities such as neopentyl esters of fatty acids with different degrees of esterification and free fatty acids) as a release agent, the same procedures, measurements, and evaluations as in Example 1 were performed. The results are shown in Table 1.

[0141] (Comparative Example 4)

[0142] Except for the use of a neopentyl ester composition containing 65% by mass of tetrastearate and 30% by mass of tripearyl ester (the residue consists of unavoidable impurities such as neopentyl esters of fatty acids with lower degrees of esterification and free fatty acids) as a release agent, and the preparation of a resin composition with a volatilization rate of 0.15% by mass at the time point of heating the resin composition at 260°C for 1 hour, the same operations, measurements, and evaluations as in Example 1 were performed. The results are shown in Table 1.

[0143] Furthermore, in Table 1, "HPSt" indicates styrene-isoprene copolymer hydrogenation. "TCD" stands for tetracyclododecene. "2020" indicates CHIMASSORB (registered trademark) 2020 FDL. "944" represents CHIMASSORB (registered trademark) 944 FDL. "GP" stands for SUMILIZER GP.

[0144] Table 1 Comparative example 4 HPSt 100 2020 2600~3400 0.1 GP 0.1 65 30 - 0.5 0.15 B C A B 3 HPSt 100 2020 2600~3400 0.1 GP 0.1 - - 90≦ 0.5 0.11 B B A C 2 HPSt 100 2020 2600~3400 0.1 GP 0.1 90≦ - - 1 0.02 A A C A 1 HPSt 100 944 2000~3100 0.1 GP 0.1 - 38 41 0.5 0.15 B C A C Implementation Examples 7 Ethylene / TCD copolymer 100 2020 2600~3400 0.1 GP 0.1 68 27 - 0.5 0.05 B B A B 6 HPSt 100 2020 2600~3400 0.1 GP 0.1 68 27 - 0.8 0.07 B B A A 5 HPSt 100 2020 2600~3400 0.1 GP 0.1 68 27 - 0.2 0.02 A A B A 4 HPSt 100 944 2000~3100 0.1 GP 0.1 75 20 - 0.5 0.02 A A B A 3 HPSt 100 2020 2600~3400 0.1 GP 0.1 55 35 - 0.5 0.09 A B A A 2 HPSt 100 2020 2600~3400 0.1 GP 0.1 - 69 25 0.5 0.07 B B A B 1 HPSt 100 2020 2600~3400 0.1 GP 0.1 68 27 - 0.5 0.04 A A A A type Content (parts by mass) type molecular weight Content (parts by mass) type Content (parts by mass) Ratio (mass%) Ratio (mass%) Ratio (mass%) Content (parts by mass) quality% Light transmittance Laser resistance Release Heat resistance to yellowing Polymers containing alicyclic structures Hindered amine compounds Hindered phenolic compounds Neopentyl tetraester of fatty acids Neopentyl tertrol fatty acid triester Neopentyl tert-3 fatty acid diester resin Light stabilizers antioxidants Release agent Volatilization resin composition evaluate

[0145] As shown in Table 1, if a resin composition containing "two or more specified fatty acid ester compounds in a specified ratio, and the proportion of volatiles measured under specified conditions is less than 0.10% by mass", it becomes possible to form an optical element with excellent laser resistance, release properties and heat resistance.

[0146] According to the present invention, a resin composition can be provided that can achieve a high level of laser resistance, release properties and heat resistance to yellowing of the obtained optical elements.

[0147] Furthermore, according to the present invention, optical elements with excellent laser resistance, release properties, and resistance to heat yellowing can be provided.

[0148] none

Claims

1. A resin composition comprising an alicyclic polymer, a hindered amine compound, and a release agent, wherein the release agent comprises two or more fatty acid ester compounds selected from the group consisting of a neopentyl tertrol fatty acid diester, a neopentyl tertrol fatty acid triester, and a neopentyl tertrol fatty acid tetraester, wherein the hydrocarbon groups of the two or more fatty acid ester compounds each have an independent carbon number of 8 to 26, and the content of one of the two or more fatty acid ester compounds is 50% by mass or more but less than 80% by mass relative to the total content of the release agent, wherein the resin composition is heated at 260°C for 1 hour. The proportion of volatiles based on the mass of the aforementioned resin composition before heating at the time point is 0.10% by mass or less; the content of the aforementioned release agent is 0.2% by mass or more and 0.8% by mass or less relative to 100 parts by mass of the aforementioned alicyclic polymer; among the aforementioned two or more fatty acid ester compounds, the content of the fatty acid ester compound with a higher degree of esterification is 50% by mass or more and less than 80% by mass relative to the total content of the aforementioned release agent; and among the fatty acid ester compounds other than the aforementioned fatty acid ester compound with a higher degree of esterification, the content of the fatty acid ester compound with the highest content is 35% by mass or less.

2. The resin composition as claimed in claim 1, wherein the content of the aforementioned release agent is 0.3% by mass or more and 0.6% by mass or less relative to 100 parts by mass of the aforementioned alicyclic polymer.

3. The resin composition as claimed in claim 1, wherein the aforementioned release agent comprises a neopentyl tert-ester of fatty acid and a neopentyl tert-ester of fatty acid.

4. The resin composition as described in any one of claims 1 to 3, wherein the content of the fatty acid ester compound with a higher degree of esterification among the aforementioned two or more fatty acid ester compounds is 60% by mass or more and 72% by mass or less relative to the total content of the aforementioned release agent.

5. An optical element comprising an alicyclic polymer, a hindered amine compound, and a release agent, wherein the release agent comprises two or more fatty acid ester compounds selected from the group consisting of a neopentyl tert-ester, a neopentyl tert-ester, and a neopentyl tert-ester, wherein the hydrocarbon groups of the two or more fatty acid ester compounds have a number of carbons of 8 to 26, and the content of one of the two or more fatty acid ester compounds is 50% by mass or more but less than 80% by mass relative to the total content of the release agent, wherein the optical element is heated at 260°C for 1 hour. The proportion of the amount of volatiles based on the mass of the aforementioned optical element before heating is 0.10% by mass or less; the content of the aforementioned release agent is 0.2% by mass or more and 0.8% by mass or less relative to 100 parts by mass of the aforementioned alicyclic polymer; among the aforementioned two or more fatty acid ester compounds, the content of the fatty acid ester compound with a higher degree of esterification is 50% by mass or more and less than 80% by mass relative to the total content of the aforementioned release agent; and among the fatty acid ester compounds other than the aforementioned fatty acid ester compound with a higher degree of esterification, the content of the fatty acid ester compound with the highest content is 35% by mass or less.

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