Photocurable resin composition and optical molded article
By adding a polysiloxane compound with a (meth)acryloyl group to photocurable resin compositions, the trade-off between contact angle and release properties is resolved, improving adhesion and release properties in optically molded bodies.
Patent Information
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- Filing Date
- 2024-09-27
- Publication Date
- 2026-04-08
AI Technical Summary
Existing photocurable resin compositions face a trade-off between the small contact angle on the surface of optically molded bodies and their release properties, leading to deteriorated adhesion between the molded body and surface coating layers.
Incorporating a polysiloxane compound with a (meth)acryloyl group into the photocurable resin composition, which balances the small contact angle and release properties by reducing surface free energy while maintaining adhesion.
The composition improves the performance balance between the small contact angle and release properties, enhancing the adhesion between the optical molded body and surface coating layers.
Smart Images

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Figure 2026060345000003
Abstract
Description
[Technical Field]
[0001] The present invention relates to a photocurable resin composition and an optically molded article. [Background technology]
[0002] In recent years, thermoplastic resins and UV-curable resin compositions have been studied for use in optical lenses from the viewpoint of heat resistance and low birefringence. Among these, methacrylic resin compositions, which are thermoplastic resins, have been studied. For example, the technologies for methacrylic resin compositions are described in Patent Documents 1 and 2.
[0003] Patent Document 1 aims to provide a methacrylic resin composition with high heat resistance, highly controlled birefringence, high light transmittance in long-path light, and excellent color tone and transparency, comprising a methacrylic resin containing at least N-substituted maleimide monomer-derived structural units in the main chain, with a glass transition temperature greater than 120°C and 160°C or less, and a resin temperature of 270°C with a shear rate of 1000 sec. ―1 Under these conditions, the melt viscosity is 250 Pa·s or less, and the absolute value of the photoelastic coefficient is 1 × 10⁻⁶. ―12 PA ―1 The following describes a methacrylic resin composition, wherein a solution of the resin composition dissolved in chloroform at a ratio of 20 mass to volume yields a light transmittance of 94% or more when measured under conditions of a path length of 100 mm and a wavelength of 470 nm, and a light transmittance of 96% or more when measured under conditions of a wavelength of 700 nm.
[0004] Patent Document 2 describes a photocurable composition that is fast-curing, non-anaerobic, low viscosity, low odor, and has excellent storage stability, and in particular, the cured product is colorless and transparent, has low optical distortion, heat resistance, low water absorption, toughness, and high hardness, and is characterized in that the photocurable composition contains a tricyclodecane skeleton di(meth)acrylate (A), a trifunctional or tetrafunctional secondary thiol (B), a cleavage-type photopolymerization initiator (C), and a hindered phenol antioxidant (D), wherein the photocurable composition does not contain a primary thiol, and the content ratio (weight ratio) of components (A), (B), (C), and (D) is within the following range. Component (A) / Component (B)=75 / 25~95 / 5 Component (C): 2 to 10 parts by weight per 100 parts by weight of the total of components (A) and (B) Component (D): 0.1 to 1 part by weight per 100 parts by weight of the total of components (A) and (B) [Prior art documents] [Patent Documents]
[0005] [Patent Document 1] Japanese Patent Publication No. 2019-35015 [Patent Document 2] Japanese Patent Publication No. 2022-32186 [Overview of the Initiative] [Problems that the invention aims to solve]
[0006] The present invention provides a photocurable resin composition that can improve the performance balance between a small contact angle on the surface of an optically molded body and the release properties of the optically molded body. [Means for solving the problem]
[0007] The inventors diligently conducted research to achieve the above objectives. As a result, they discovered that the compounds contained in the photocurable resin composition used to produce optical molded articles are related to the balance between the small contact angle of the optical molded article's surface and the release properties of the optical molded article. Based on this finding, the inventors further diligently conducted research and discovered that including a polysiloxane compound having a (meth)acryloyl group in the photocurable resin composition used to produce optical molded articles can improve the balance between the small contact angle of the optical molded article's surface and the release properties of the optical molded article, thus completing the present invention.
[0008] [1] A photocurable resin composition that can be used in optically molded articles, It comprises a (meth)acrylate monomer and a polysiloxane compound, The (meth)acrylate monomer includes a (meth)acrylate monomer with two or more functionalities, The polysiloxane compound is a photocurable resin composition having a (meth)acryloyl group. [2] The photocurable resin composition according to [1], wherein the molecular weight calculated from the functional group equivalent of the polysiloxane compound is 200 g / mol or more and 5,000 g / mol or less. [3] The photocurable resin composition according to [1] or [2], wherein the content of the polysiloxane compound is 0.005 parts by mass or more and 10 parts by mass or less, when the content of the (meth)acrylate monomer is 100 parts by mass. [4] The photocurable resin composition according to any one of [1] to [3], wherein the bifunctional or more (meth)acrylate monomer comprises one or more selected from the group consisting of alicyclic bifunctional (meth)acrylate monomers and linear bifunctional (meth)acrylate monomers. [5] The photocurable resin composition according to [4], wherein the total content of the alicyclic bifunctional (meth)acrylate monomer and the linear bifunctional (meth)acrylate monomer is 60 parts by mass or more and 100 parts by mass or less, when the total content of the bifunctional or more (meth)acrylate monomers is 100 parts by mass. [6] The photocurable resin composition according to any one of [1] to [5], wherein the content of the bifunctional or more (meth)acrylate monomer is 5 parts by mass or more and 100 parts by mass or less when the total content of the (meth)acrylate monomer is 100 parts by mass. [7] The photocurable resin composition according to any one of [1] to [6], further comprising a monofunctional (meth)acrylate monomer. [8] The photocurable resin composition according to [7], wherein the monofunctional (meth)acrylate monomer has an alicyclic skeleton. [9] A photocurable resin composition according to any one of [1] to [8] above, wherein the contact angle between the cured film and water, measured in accordance with the following <cured film production conditions> as measured in accordance with JIS R 3257:1999, is 90 degrees or less. <Conditions for preparing cured film> A 3.0mm thick, 50mm x 50mm silicone sheet (material: silicone rubber, hardness: 50 degrees) with a 35mm diameter circular hole is placed on a 0.7mm thick, 50mm x 50mm alkali-free glass sheet. The photocurable resin composition is then filled into the circular hole. Another 0.7mm thick, 50mm x 50mm alkali-free glass sheet is placed on top of the silicone sheet. The height is adjusted using a SUS lab jack. The photocurable resin composition is then irradiated with 405nm wavelength LED light at 810mW for 3 minutes from above the alkali-free glass. After that, it is turned over and irradiated with 405nm wavelength LED light at 810mW for 3 minutes. Finally, it is allowed to cool at 23°C for 30 minutes to release the cured photocurable resin composition from the alkali-free glass and the silicone sheet, thereby obtaining a cured film.
[10] The light-curable resin composition according to any one of [1] to [9], wherein the haze value of the cured film produced according to the following <Cured Film Production Conditions> and measured according to JIS K 7136:2000 under the condition of a thickness of 3.0 mm is 1.3% or less. <Cured Film Production Conditions> Place a 3.0 mm thick, 50 mm × 50 mm silicone sheet (material: silicone rubber, hardness: 50 degrees) with a 35 mmφ circular hole on a 0.7 mm thick, 50 mm × 50 mm non-alkali glass, fill the circular hole portion with the light-curable resin composition, then place a 0.7 mm thick, 50 mm × 50 mm non-alkali glass on it, place this on a SUS-made laboratory jack to adjust the height, irradiate the light-curable resin composition with LED light of wavelength 405 nm under the condition of 810 mW for 3 minutes from above the non-alkali glass, turn it over, irradiate with LED light of wavelength 405 nm under the condition of 810 mW for 3 minutes, then let it cool at 23°C for 30 minutes, and release the cured product of the light-curable resin composition from the non-alkali glass and the silicone sheet to obtain a cured film.
[11] The light-curable resin composition according to any one of [1] to
[10] , further comprising an antioxidant.
[12] The light-curable resin composition according to any one of [1] to
[11] , further comprising a photoinitiator.
[13] The light-curable resin composition according to
[12] , wherein the photoinitiator comprises a photo radical polymerization initiator.
[14] The light-curable resin composition according to any one of [1] to
[13] , further comprising a light stabilizer.
[15] The light-curable resin composition according to any one of [1] to
[14] , which can be used in the casting method.
[16] A photocurable resin composition according to any one of the above [1] to
[15] , which can be used for one or more lenses selected from the group consisting of virtual reality lenses (VR lenses), mixed reality lenses (MR lenses), augmented reality lenses (AR lenses), cross-reality lenses (xR lenses), and head-mounted display lenses (HMD lenses).
[17] An optically molded article comprising a cured product of a photocurable resin composition according to any of the above [1] to
[16] .
[18] The optical molded body according to
[17] , wherein the optical molded body includes a lens.
[19] The optical molded body according to
[18] , wherein the lens includes one or more selected from the group consisting of virtual reality lenses (VR lenses), mixed reality lenses (MR lenses), augmented reality lenses (AR lenses), cross-reality lenses (xR lenses), and head-mounted display lenses (HMD lenses).
[20] The optical molded body according to
[17] , wherein the optical molded body includes a cover display. [twenty one] The optical molded body according to
[20] , wherein the cover display includes one or more selected from the group consisting of a cover display for virtual reality, a cover display for mixed reality, a cover display for augmented reality, a cover display for cross-reality, and a cover display for a head-mounted display. [Effects of the Invention]
[0009] According to the present invention, it is possible to provide a photocurable resin composition that can improve the performance balance between the small contact angle of the surface of the optically molded body and the release properties of the optically molded body. [Modes for carrying out the invention]
[0010] In this specification, the term "(meth)acrylate" refers to a concept that encompasses both acrylate and methacrylate. The same applies to similar terms such as "(meth)acryloyl." Each component in this embodiment may be used individually or in combination of two or more. Furthermore, the "~" symbol representing a numerical range indicates "greater than or equal to" and "less than or equal to," including both the upper and lower limits.
[0011] Conventionally, a method of adding a release agent to a photocurable resin composition has been known to improve the release properties of optically molded articles obtained from the photocurable resin composition. However, the inventors have found that while adding a release agent to a photocurable resin composition improves the release properties of the optically molded article, there are cases where the surface free energy of the optically molded article becomes too small (the contact angle of the surface of the optically molded article becomes too large). In other words, the inventors have found that there is a trade-off relationship between the small contact angle of the surface of the optically molded article and the release properties of the optically molded article. Furthermore, it became clear that if the surface free energy of the optically molded body becomes too small (i.e., if the contact angle of the surface of the optically molded body becomes too large), the adhesion between the optically molded body and the surface coating layer deteriorates. In other words, the inventors also found that there is a trade-off relationship between the release properties of the optically molded body and the adhesion between the optically molded body and the surface coating layer.
[0012] (Photocurable resin composition) The photocurable resin composition of this embodiment (hereinafter also referred to as simply "resin composition" as appropriate) is a photocurable resin composition that can be used in optically molded articles. The photocurable resin composition of this embodiment comprises a (meth)acrylate monomer (A) and a polysiloxane compound (E). The (meth)acrylate monomer (A) comprises a bifunctional or more (meth)acrylate monomer (A2). The polysiloxane compound (E) has a (meth)acryloyl group. The photocurable resin composition of this embodiment, having the above-described configuration, can improve the balance between the small contact angle of the optical molded body surface and the release properties of the optical molded body.
[0013] The reason for this is not entirely clear, but the following reasons can be inferred. The inclusion of polysiloxane compound (E) in the photocurable resin composition of this embodiment is thought to reduce the surface free energy of the optically molded article obtained from the photocurable resin composition of this embodiment. This is thought to improve the release properties of the optically molded article obtained from the photocurable resin composition of this embodiment. Furthermore, it is believed that the presence of a polar (meth)acryloyl group in the polysiloxane compound (E) of this embodiment can mitigate the problem of the surface free energy of the optically molded article becoming too small. Therefore, it is believed that the release properties of the optically molded article obtained from the photocurable resin composition of this embodiment can be improved while maintaining a small contact angle on the surface of the optically molded article. Furthermore, by improving the performance balance between the small contact angle of the optical molded body surface and the release properties of the optical molded body, it is believed that the performance balance between the adhesion between the optical molded body and the surface coating layer and the release properties of the optical molded body can also be improved.
[0014] The properties of the photocurable resin composition are not particularly limited. However, from the viewpoint of suitability for forming optically molded articles by injection molding or casting, the photocurable resin composition is preferably in liquid form. Furthermore, from the viewpoint of improving the design freedom of optically molded articles, photocurable resin compositions are preferably used in molding by the casting method.
[0015] Next, we will explain the components of photocurable resin compositions with specific examples. The photocurable resin composition comprises a (meth)acrylate monomer (A) and a polysiloxane compound (E). The photocurable resin composition may also consist of (meth)acrylate monomer (A) and polysiloxane compound (E), and may contain components other than (meth)acrylate monomer (A) and polysiloxane compound (E). The photocurable resin composition may also contain, as specific examples of other components, one or more selected from the group consisting of antioxidants (B), photopolymerization initiators (C), and light stabilizers (D), as described later.
[0016] <(meth)acrylate monomer (A)> (Meth)acrylate monomer (A) is a compound having a (meth)acryloyl group. (Meth)acrylate monomer (A) is a molecule that can bond with other molecules through radical polymerization of the (meth)acryloyl group.
[0017] The (meth)acrylate monomer (A) of this embodiment includes a bifunctional or more (meth)acrylate monomer (A2) from the viewpoint of improving the balance between the small contact angle of the optical molded body surface and the release properties of the optical molded body.
[0018] In the photocurable resin composition of this embodiment, the content of bifunctional or more (meth)acrylate monomer (A2) is preferably 5 to 100 parts by mass, more preferably 8 to 90 parts by mass, even more preferably 10 to 70 parts by mass, even more preferably 13 to 50 parts by mass, even more preferably 15 to 30 parts by mass, and even more preferably 15 to 25 parts by mass, when the total content of (meth)acrylate monomer (A) in the photocurable resin composition of this embodiment is 100 parts by mass.
[0019] The (meth)acrylate monomer (A) of this embodiment preferably further comprises a monofunctional (meth)acrylate monomer (A1) from the viewpoint of further improving the performance balance between the small contact angle of the optical molded body surface and the release properties of the optical molded body.
[0020] The content of monofunctional (meth)acrylate monomer (A1) in the photocurable resin composition of this embodiment is preferably 0 to 95 parts by mass, more preferably 10 to 92 parts by mass, even more preferably 30 to 90 parts by mass, even more preferably 50 to 87 parts by mass, even more preferably 70 to 85 parts by mass, and even more preferably 75 to 85 parts by mass, when the total content of (meth)acrylate monomer (A) in the photocurable resin composition of this embodiment is 100 parts by mass.
[0021] In the photocurable resin composition of this embodiment, the mass ratio of the content of bifunctional or more (meth)acrylate monomers (A2) to the content of monofunctional (meth)acrylate monomers (A1) is preferably 0.50 to 10.0, more preferably 1.0 to 8.0, even more preferably 2.0 to 6.0, even more preferably 3.0 to 5.0, and even more preferably 3.5 to 4.5, from the viewpoint of further improving the performance balance between the small contact angle of the surface of the optically molded body and the release properties of the optically molded body.
[0022] In this embodiment, the content of (meth)acrylate monomer (A) in the photocurable resin composition is preferably 70% to 100% by mass, more preferably 80% to 99% by mass, even more preferably 85% to 98% by mass, and even more preferably 90% to 97% by mass, when the total amount of solids in the photocurable resin composition (total amount of components remaining as solids when cured) is taken as 100% by mass.
[0023] <Monofunctional (meth)acrylate monomer (A1)> Monofunctional (meth)acrylate monomers (A1) include, for example, one or more selected from the group consisting of aromatic ring monofunctional (meth)acrylate monomers, alicyclic monofunctional (meth)acrylate monomers, and chain monofunctional (meth)acrylate monomers. Chain monofunctional (meth)acrylate monomers include one or more selected from the group consisting of linear monofunctional (meth)acrylate monomers and branched monofunctional (meth)acrylate monomers. Linear monofunctional (meth)acrylate monomers include monofunctional (meth)acrylate monomers having a linear hydrocarbon skeleton. Branched monofunctional (meth)acrylate monomers include monofunctional (meth)acrylate monomers having a branched hydrocarbon skeleton.
[0024] The monofunctional (meth)acrylate monomer (A1) is preferably isobornyl (meth)acrylate, dicyclopentanyl (meth)acrylate (e.g., GM81HDA, manufactured by Kokusei Chemical Co., Ltd.), 3,3,5-trimethylcyclohexyl (meth)acrylate, 4-tert-butylcyclohexyl (meth)acrylate, dicyclopentenyl (meth)acrylate (e.g., FA-511AS, manufactured by Hitachi Chemical Co., Ltd.), dicyclopentenyloxyethyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, 2-hydroxyethyl (meth) Acrylate, 4-hydroxybutyl (meth)acrylate, isobutyl (meth)acrylate, t-butyl (meth)acrylate, isooctyl (meth)acrylate, 2-methoxyethyl (meth)acrylate, methoxytriethylene glycol (meth)acrylate, 2-ethoxyethyl (meth)acrylate, 3-methoxybutyl (meth)acrylate, ethoxyethyl (meth)acrylate, butoxyethyl (meth)acrylate, ethoxydiethylene glycol (meth)acrylate, methoxydioxyethyl (meth)acrylate, ethoxyethyl (meth)acrylate, Dimethylglycol (meth)acrylate, cyclic trimethylolpropane formal mono(meth)acrylate, imide (meth)acrylate, isoamyl (meth)acrylate, ethoxylated succinic acid (meth)acrylate, trifluoroethyl (meth)acrylate, ω-carboxypolycaprolactone mono(meth)acrylate, cyclohexyl (meth)acrylate, 2-(2-ethoxyethoxy)ethyl (meth)acrylate, stearyl (meth)acrylate, isostearyl (meth)acrylate (e.g., S-1800A, Shin Nakamura Chemical Co., Ltd.) (Manufactured by Osaka Organic Chemical Industry Co., Ltd.), diethylene glycol monobutyl ether (meth)acrylate, lauryl (meth)acrylate (e.g., LA, manufactured by Osaka Organic Chemical Industry Co., Ltd.), isodecyl (meth)acrylate, isooctyl (meth)acrylate, octyl / decyl (meth)acrylate, tridecyl (meth)acrylate, caprolactone (meth)acrylate, ethoxylated (4) nonylphenol (meth)acrylate, methoxypolyethylene glycol (350) mono(meth)acrylate, methoxypolyethylene glycol (550) mono(meth)acrylate,Phenoxyethyl (meth)acrylate, cyclohexyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, benzyl (meth)acrylate, methylphenoxyethyl (meth)acrylate, caprolactone-modified tetrahydrofurfuryl (meth)acrylate, tribromophenyl (meth)acrylate, ethoxylated tribromophenyl (meth)acrylate, 2-phenoxyethyl (meth)acrylate, ethylene oxide adduct of 2-phenoxyethyl (meth)acrylate, propylene glycol of 2-phenoxyethyl (meth)acrylate It contains one or more substances selected from the group consisting of oxide adducts, phenoxydiethylene glycol (meth)acrylate, 2-hydroxy-3-phenoxypropyl (meth)acrylate, 3-methacryloyloxymethylcyclohexene oxide, 3-(meth)acryloyloxymethylcyclohexene oxide, ethoxylated-o-phenylphenol (meth)acrylate (e.g., A-LEN-10, manufactured by Shin-Nakamura Chemical Industry Co., Ltd.), 2-methacryloyloxy-2-methyladamantane, 2-methacryloyloxy-2-ethyladamantane, etc.
[0025] The monofunctional (meth)acrylate monomer (A1) preferably has an alicyclic skeleton, from the viewpoint of further improving the performance balance between a small contact angle on the surface of the optically molded article and the release properties of the optically molded article. More preferably, the monofunctional (meth)acrylate monomer (A1) comprises an alicyclic monofunctional (meth)acrylate monomer, even more preferably comprises dicyclopentanyl (meth)acrylate, and even more preferably comprises dicyclopentanyl methacrylate.
[0026] <(Meth)acrylate monomers (A2) with two or more functional properties> The (meth)acrylate monomer (A2) includes, for example, one or more selected from the group consisting of two or more bifunctional aromatic ring (meth)acrylate monomers, two or more bifunctional alicyclic (meth)acrylate monomers, and two or more bifunctional chain (meth)acrylate monomers. The chain (meth)acrylate monomer includes, for example, one or more selected from the group consisting of two or more bifunctional linear (meth)acrylate monomers and two or more bifunctional branched (meth)acrylate monomers. The linear (meth)acrylate monomer includes, for example, a bifunctional (meth)acrylate monomer having a linear hydrocarbon skeleton. The branched (meth)acrylate monomer includes, for example, a bifunctional (meth)acrylate monomer having a branched hydrocarbon skeleton. The (meth)acrylate monomer (A2) includes, for example, one or more selected from the group consisting of aromatic ring difunctional (meth)acrylate monomers, alicyclic difunctional (meth)acrylate monomers, and chain-type difunctional (meth)acrylate monomers. The chain-type difunctional (meth)acrylate monomer includes, for example, one or more selected from the group consisting of linear difunctional (meth)acrylate monomers and branched chain difunctional (meth)acrylate monomers. The linear difunctional (meth)acrylate monomer includes, for example, a difunctional (meth)acrylate monomer having a linear hydrocarbon skeleton. The branched chain difunctional (meth)acrylate monomer includes, for example, a difunctional (meth)acrylate monomer having a branched hydrocarbon skeleton.
[0027] Alicyclic bifunctional (meth)acrylate monomers are bifunctional (meth)acrylate monomers having an alicyclic hydrocarbon structure in their molecular structure. From the viewpoint of improving heat resistance, the number of carbon atoms in the alicyclic hydrocarbon structure is preferably 4 to 14, more preferably 5 to 12, and even more preferably 6 to 10. The alicyclic hydrocarbon structure may be a saturated hydrocarbon structure or an unsaturated hydrocarbon structure. From the viewpoint of improving heat resistance, the alicyclic hydrocarbon structure is preferably a saturated hydrocarbon structure.
[0028] Furthermore, the alicyclic hydrocarbon structure may be a monocyclic hydrocarbon structure, or a polycyclic hydrocarbon structure such as a condensed cyclic hydrocarbon structure or a bridged cyclic hydrocarbon structure. The alicyclic difunctional (meth)acrylate monomer may contain groups containing these alicyclic hydrocarbon structures in its molecular structure, preferably containing divalent groups containing alicyclic hydrocarbon structures. Specific examples of monocyclic hydrocarbon groups include groups having a cycloalkane structure, such as cyclohexylene and cyclohexyl groups; and groups having a cycloalkene skeleton, such as cyclodecatrienediyl and cyclodecatriene groups. Specific examples of polycyclic hydrocarbon groups include groups having a dicyclopentadiene skeleton such as tricyclodecanediyl, dicyclopentanyl, and dicyclopentenyl; groups having a norbornane skeleton such as norbornanediyl, isobornanediyl, norbornyl, and isobornyl; and groups having an adamantane skeleton such as adamantanediyl and adamantyl.
[0029] A linear, bifunctional (meth)acrylate monomer is a (meth)acrylate that has a linear structure in its molecular structure and contains two (meth)acryloyl groups. The linear structure preferably includes a divalent linear hydrocarbon group, from the viewpoint of improving crack resistance during molding of the optically molded article. The number of carbon atoms in the divalent linear hydrocarbon group is, for example, 1 or more, preferably 2 or more, and more preferably 4 or more, from the viewpoint of reducing liquid volume deviations due to monomer volatilization during molding of the optically molded article. Furthermore, from the viewpoint of improving heat resistance, the number of carbon atoms in the divalent linear hydrocarbon group is preferably 20 or less, and more preferably 14 or less.
[0030] A specific example of a linear, bifunctional (meth)acrylate monomer is the di(meth)acrylate of an alkanediol. The linear bifunctional (meth)acrylate monomers are preferably 1,6-hexanediol di(meth)acrylate (e.g., A-HD-N, manufactured by Shin-Nakamura Chemical Industry Co., Ltd.; HD-N: manufactured by Shin-Nakamura Chemical Industry Co., Ltd.), 1,9-nonanediol di(meth)acrylate (e.g., A-NOD-N, manufactured by Shin-Nakamura Chemical Industry Co., Ltd.; light acrylate 1,9ND-A, manufactured by Kyoeisha Chemical Co., Ltd.; NOD-N, manufactured by Shin-Nakamura Chemical Industry Co., Ltd.; light acrylate 1,9ND-M, manufactured by Kyoeisha Chemical Co., Ltd.), 1,10-decanediol di(meth)acrylate (e.g., A-DOD-N, manufactured by Shin-Nakamura Chemical Industry Co., Ltd.; DOD-N, manufactured by Shin-Nakamura Chemical Industry Co., Ltd.), 1,12-dodecanediol di It comprises one or more substances selected from the group consisting of (meth)acrylate (e.g., DDD, manufactured by Shin-Nakamura Chemical Industry Co., Ltd.; SR262, manufactured by Arkema), ethylene glycol di(meth)acrylate (e.g., SR206NS, manufactured by Arkema), triethylene glycol di(meth)acrylate (e.g., SR272, manufactured by Arkema), polyethylene glycol di(meth)acrylate (e.g., A-400, manufactured by Shin-Nakamura Chemical Industry Co., Ltd.), 1,3-butanediol di(meth)acrylate (e.g., BG, manufactured by Shin-Nakamura Chemical Industry Co., Ltd.), and 1,4-butanediol di(meth)acrylate (e.g., BD, manufactured by Shin-Nakamura Chemical Industry Co., Ltd.).
[0031] The bifunctional or more (meth)acrylate monomer (A2) of this embodiment preferably comprises one or more selected from the group consisting of bifunctional or more alicyclic (meth)acrylate monomers and bifunctional or more linear (meth)acrylate monomers, from the viewpoint of further improving the balance between the small contact angle of the surface of the optically molded body and the release properties of the optically molded body, more preferably comprises one or more selected from the group consisting of bifunctional or more alicyclic (meth)acrylate monomers and linear bifunctional (meth)acrylate monomers, even more preferably comprises linear bifunctional (meth)acrylate monomers, even more preferably comprises 1,12-dodecanediol di(meth)acrylate, and even more preferably comprises 1,12-dodecanediol dimethacrylate.
[0032] In this embodiment, the total content of alicyclic bifunctional (meth)acrylate monomers and linear bifunctional (meth)acrylate monomers in the photocurable resin composition is preferably 60 parts by mass or more and 100 parts by mass or less, more preferably 70 parts by mass or more and 100 parts by mass or less, even more preferably 80 parts by mass or more and 100 parts by mass or less, even more preferably 90 parts by mass or more and 100 parts by mass or less, and even more preferably 95 parts by mass or more and 100 parts by mass or less, when the total content of bifunctional or more (meth)acrylate monomers (A2) in the photocurable resin composition of this embodiment is 100 parts by mass.
[0033] <Polysiloxane compound (E)> Polysiloxane compounds (E) are compounds having a polysiloxane skeleton with a repeating siloxane bond structure. Polysiloxane compounds (E) are compounds that can have various organic groups on the Si atoms of the polysiloxane skeleton.
[0034] The polysiloxane compound (E) of this embodiment has a (meth)acryloyl group, which improves the balance between the small contact angle on the surface of the optically molded body and the release properties of the optically molded body. The polysiloxane compound (E) of this embodiment preferably has one or two (meth)acryloyl groups, from the viewpoint of further improving the balance between the small contact angle of the optical molded body surface and the release properties of the optical molded body.
[0035] The polysiloxane compound (E) of this embodiment preferably includes one or more compounds selected from the group consisting of compounds represented by the following formula (1) and compounds represented by the following formula (2), from the viewpoint of further improving the balance between the small contact angle of the surface of the optically molded body and the release properties of the optically molded body. The polysiloxane compound (E) represented by the following formula (1) is a polysiloxane compound having one (meth)acryloyl group in the molecule (hereinafter, sometimes referred to as polysiloxane compound (E1)). Further, the polysiloxane compound (E) represented by the following formula (2) is a polysiloxane compound having two (meth)acryloyl groups in the molecule (hereinafter, sometimes referred to as polysiloxane compound (E2)).
[0036] [Chemical formula]
[0037] In formula (1), R 1 represents a hydrogen atom or a methyl group. Each R 2 independently represents a hydrocarbon group having 2 to 10 carbon atoms. Each R 3 independently represents an alkyl group having 1 to ́4 carbon atoms. n represents an integer in the range of 4 to 100.
[0038] R in formula (1) 1 is preferably one or more selected from the group consisting of a hydrogen atom and a methyl group, more preferably a methyl group, from the viewpoint of further improving the performance balance between the small contact angle of the surface of the optical molding body and the mold release property of the optical molding body. R in formula (1) 2 is preferably one or more selected from the group consisting of a methylene group, an ethylene group, a propylene group, a butylene group, a tetramethylene group, a hexamethylene group, an octamethylene group, a 1,2-cyclohexene group, a 1,3-cyclohexene group , a 1,4-cyclohexene group, and a 2-methylpropene group, more preferably one or more selected from the group consisting of a methylene group, an ethylene group, a propylene group, a butylene group, a tetramethylene group, a hexamethylene group, and an octamethylene group. R in formula (1) 3From the viewpoint of further improving the balance between the small contact angle of the optical molded body surface and the release properties of the optical molded body, a methyl group is preferred. In formula (1), n is preferably 5 to 200, more preferably 15 to 170, and even more preferably 30 to 100, from the viewpoint of further improving the balance between the small contact angle of the optical molded body surface and the release properties of the optical molded body.
[0039] Polysiloxane compounds (E1) include, for example, Cylaprene FM-0711 (manufactured by JNC Corporation, number average molecular weight Mn: 1,000), Cylaprene FM-0721 (manufactured by JNC Corporation, number average molecular weight Mn: 5,000), Cylaprene FM-0725 (manufactured by JNC Corporation, number average molecular weight Mn: 10,000), Cylaprene TM-0701T (manufactured by JNC Corporation, number average molecular weight Mn: 423), and X-22-174ASX (Shin-Etsu Chemical). It contains one or more types selected from the group consisting of (manufactured by Gaku Kogyo Co., Ltd., number average molecular weight Mn: 900), X-22-174BX (manufactured by Shin-Etsu Chemical Co., Ltd., number average molecular weight Mn: 2,300), KF-2012 (manufactured by Shin-Etsu Chemical Co., Ltd., number average molecular weight Mn: 4,600), X-22-242 (manufactured by Shin-Etsu Chemical Co., Ltd., number average molecular weight Mn: 12,000), and X-22-2404 (manufactured by Shin-Etsu Chemical Co., Ltd., number average molecular weight Mn: 420).
[0040] [ka]
[0041] In equation (2), R 1 Each of these independently represents either a hydrogen atom or a methyl group. 2 Each of these independently represents a hydrocarbon group having 2 to 10 carbon atoms. 3 Each of these independently represents an alkyl group with 1 to 4 carbon atoms. n represents an integer in the range of 4 to 100.
[0042] R in equation (2) 1From the viewpoint of further improving the balance between the small contact angle of the optical molded body surface and the release properties of the optical molded body, it is preferably one or more selected from the group consisting of hydrogen atoms and methyl groups, and more preferably a methyl group. R in equation (2) 2 From the viewpoint of further improving the balance between the small contact angle of the optical molded body surface and the release properties of the optical molded body, it is preferably one or more selected from the group consisting of methylene group, ethylene group, propylene group, butylene group, tetramethylene group, hexamethylene group, octamethylene, 1,2-cyclohexene group, 1,3-cyclohexene group, 1,4-cyclohexene group, and 2-methylpropene group, and more preferably one or more selected from the group consisting of methylene group, ethylene group, propylene group, butylene group, tetramethylene group, hexamethylene group, and octamethylene group. R in equation (2) 3 From the viewpoint of further improving the balance between the small contact angle of the optical molded body surface and the release properties of the optical molded body, a methyl group is preferred. In formula (2), n is preferably 5 to 200, more preferably 15 to 170, and even more preferably 30 to 100, from the viewpoint of further improving the performance balance between the small contact angle of the optical molded body surface and the release properties of the optical molded body.
[0043] Polysiloxane compounds (E2) include, for example, Cyraprene FM-7711 (manufactured by JNC Corporation, number average molecular weight Mn: 1,000), Cyraprene FM-7721 (manufactured by JNC Corporation, number average molecular weight Mn: 5,000), Cyraprene FM-7725 (manufactured by JNC Corporation, number average molecular weight Mn: 10,000), X-22-164 (manufactured by Shin-Etsu Chemical Co., Ltd., number average molecular weight Mn: 380), X-22-164AS (manufactured by Shin-Etsu Chemical Co., Ltd., number average molecular weight Mn: 900), It contains one or more types selected from the group consisting of X-22-164A (manufactured by Shin-Etsu Chemical Co., Ltd., number average molecular weight Mn: 1,740), X-22-164B (manufactured by Shin-Etsu Chemical Co., Ltd., number average molecular weight Mn: 3,200), X-22-164C (manufactured by Shin-Etsu Chemical Co., Ltd., number average molecular weight Mn: 4,800), X-22-164E (manufactured by Shin-Etsu Chemical Co., Ltd., number average molecular weight Mn: 7,800), and X-22-2445 (manufactured by Shin-Etsu Chemical Co., Ltd., number average molecular weight Mn: 3,200).
[0044] From the viewpoint of further improving the balance between the small contact angle of the optical molded surface and the release properties of the optical molded body, the content of polysiloxane compound (E) in the photocurable resin composition of this embodiment is preferably 0.005 parts by mass or more and 10 parts by mass or less, more preferably 0.01 parts by mass or more and 8.0 parts by mass or less, even more preferably 0.05 parts by mass or more and 6.0 parts by mass or less, and even more preferably 0.1 parts by mass or more and 5.0 parts by mass or less, when the content of (meth)acrylate monomer (A) in the photocurable resin composition of this embodiment is 100 parts by mass.
[0045] In this embodiment, the content of polysiloxane compound (E) in the photocurable resin composition is preferably 0.01% to 10% by mass, more preferably 0.02% to 8.0% by mass, even more preferably 0.04% to 6.0% by mass, and even more preferably 0.05% to 5.0% by mass, when the total amount of solids in the photocurable resin composition (total amount of components remaining as solids when cured) is taken as 100% by mass.
[0046] In this embodiment, the total content of (meth)acrylate monomer (A) and polysiloxane compound (E) in the photocurable resin composition is preferably 70% to 100% by mass, more preferably 80% to 99% by mass, even more preferably 90% to 98% by mass, and even more preferably 93% to 97% by mass, when the total amount of solids in the photocurable resin composition (total amount of components remaining as solids when cured) is taken as 100% by mass.
[0047] In this embodiment, the molecular weight calculated from the functional group equivalent of the polysiloxane compound (E) is preferably 200 g / mol or more and 5,000 g / mol or less, more preferably 250 g / mol or more and 4,000 g / mol or less, even more preferably 300 g / mol or more and 3,000 g / mol or less, even more preferably 350 g / mol or more and 2,000 g / mol or less, and even more preferably 400 g / mol or more and 1,000 g / mol or less, from the viewpoint of further improving the performance balance between the small contact angle of the surface of the optically molded body and the release properties of the optically molded body.
[0048] In this embodiment, the method for calculating the molecular weight from the functional group equivalent of the polysiloxane compound (E) can be specifically the method described in the examples. Furthermore, the functional group equivalent can also be measured using, for example, the following <Method for Measuring Functional Group Equivalent>.
[0049] <Method for measuring functional group equivalents> First, the hydroxyl value (unit: mgKOH / g) of the polysiloxane compound (E) having a (meth)acryloyl group in this embodiment is measured. The hydroxyl value is the amount of hydroxyl groups per 1 g of resin calculated by esterifying or acetylating the hydroxyl groups derived from the (meth)acryloyl group in the polysiloxane compound (E), and then back-titrating the remaining acid with an alkali, and then converting this value to the number of mg of potassium hydroxide. The hydroxyl value can be measured according to JIS K 0070:1992. Functional group equivalent (unit: g / mol) is the number of grams of a compound containing 1 mole equivalent of a functional group. The functional group equivalent can be calculated using the following formula (3). Equation (3): [Functional group equivalent (g / mol)] = [Molecular weight of potassium hydroxide (mgKOH / mol)] / [Hydroxyl value (mgKOH / g)]
[0050] In this embodiment, the number-average molecular weight Mn of the polysiloxane compound (E) having a (meth)acryloyl group is preferably 200 to 5,000, more preferably 250 to 4,000, even more preferably 300 to 3,000, even more preferably 350 to 2,000, and even more preferably 400 to 1,000, from the viewpoint of further improving the performance balance between the small contact angle of the surface of the optically molded body and the release properties of the optically molded body. Specifically, the method for measuring the number-average molecular weight Mn of the polysiloxane compound (E) in this embodiment can be the <Method for measuring number-average molecular weight Mn> described below.
[0051] <Method for measuring the number-average molecular weight (Mn)> Using gel permeation chromatography (GPC), the number-average molecular weight Mn of a polysiloxane compound (E) dissolved in the mobile phase can be measured under the following conditions. • Column: Two PLgel 5μm MIXED-D, 300×7.5mm (manufactured by Agilent Technologies) columns joined together. Column temperature: 40°C Mobile phase: Tetrahydrofuran for HPLC [containing stabilizer] (Fujifilm Wako Pure Chemical Industries) ·Flow rate: 1.0mL / min ·Injection volume: 100μL • Detection method: Differential refractive index detection • Column calibration: Monodisperse polystyrene (Product name: EasiCal Type PS-1 polystyrene, manufactured by Agilent Technologies) • Molecular weight calibration: Relative calibration method (polystyrene equivalent) • Pump system: KP-22-13S Dual Pump (manufactured by From Co., Ltd.) • Automatic injection device: 717plus (manufactured by Waters Japan Co., Ltd.) • Detection device: Differential refractive index detector (Product name: RI-101, manufactured by Shodex)
[0052] <Antioxidant (B)> The photocurable resin composition of this embodiment may further contain antioxidant (B). Antioxidant (B) is not particularly limited, and known antioxidants can be used. Antioxidant (B) includes, for example, one or more selected from the group consisting of phenolic antioxidants, phosphorus antioxidants, sulfur-based antioxidants, hindered amine antioxidants, and thioether antioxidants.
[0053] Examples of phenolic antioxidants include 2,6-di-t-butylhydroxytoluene and pentaerythritol tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate]. Examples of commercially available phenolic antioxidants include AO-20, AO-30, AO-40, AO-50, AO-60, and AO-80 from the ADEKA Corporation's ADEKA Stab series.
[0054] Examples of phosphorus-based antioxidants include phosphines such as trialkylphosphines and triarylphosphines, trialkyl phosphites, and triaryl phosphites. Examples of commercially available phosphorus-based antioxidants include the ADEKA Stab series from ADEKA Corporation, such as PEP-4C, PEP-8, PEP-24G, PEP-36, HP-10, 260, 522A, 329K, 1178, 1500, 135A, and 3010.
[0055] Examples of sulfur-based antioxidants include dilauryl 3,3-thiodipropionate, dimyristyl 3,3'-thiodipropionate, distearyl 3,3-thiodipropionate, laurylstearyl 3,3-thiodipropionate, pentaerythritol-tetrakis-(β-lauryl-thio-propionate), and 3,9-bis(2-dodecylthioethyl)-2,4,8,10-tetraoxaspiro[5,5]undecane.
[0056] Examples of hindered amine antioxidants include bis(1,2,2,6,6-pentamethyl-4-piperidinyl) sebacate, methyl(1,2,2,6,6-pentamethyl-4-piperidinyl) sebacate, 2,4-bis[N-butyl-N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidine-4-yl)amino]-6-(2-hydroxyethylamine)-1,3,5-triazine, bis(2,2,6,6-tetramethyl-1-(octyloxy)-4-piperidinyl) decandioate, and bis(1,2,2,6,6-pentamethyl-4-piperidyl) sebacate. Examples of commercially available hindered amine antioxidants include AL-72 from ADEKA Corporation's ADEKA Stab series, and 111FDL, 123, 144, 152, 292, and 5100 from BASF's TINUVIN series.
[0057] Examples of thioether-based antioxidants include ditridecyl 3,3'-thiobispropionate and bis[3-(dodecylthio)propionate]2,2-bis[[3-(dodecylthio)-1-oxopropyloxy]methyl]-1,3-propanediyl. Examples of commercially available thioether-based antioxidants include AO-26, AO-412S, and AO-503A from the ADEKA Stab series manufactured by ADEKA Corporation.
[0058] From the viewpoint of reducing discoloration of the optically molded product, antioxidant (B) preferably comprises one or more selected from the group consisting of phenolic antioxidants and thioether antioxidants. From the viewpoint of further reducing discoloration of the optically molded product, antioxidant (B) more preferably comprises one or more selected from the group consisting of bis[3-(dodecylthio)propionic acid]2,2-bis[[3-(dodecylthio)-1-oxopropyloxy]methyl]-1,3-propanediyl (e.g., Adekastab AO-412S, manufactured by ADEKA Corporation) and pentaerythritol tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate] (e.g., Adekastab AO-60, manufactured by ADEKA Corporation).
[0059] From the viewpoint of further improving the performance balance between the contact angle of the optical molded body surface and the transparency of the optical molded body, the content of antioxidant (B) in the photocurable resin composition of this embodiment is preferably 0.010 parts by mass or more and 10 parts by mass or less, more preferably 0.050 parts by mass or more and 5.0 parts by mass or less, even more preferably 0.10 parts by mass or more and 3.0 parts by mass or less, even more preferably 0.20 parts by mass or more and 2.0 parts by mass or less, and even more preferably 0.50 parts by mass or more and 1.5 parts by mass or less, when the content of (meth)acrylate monomer (A) in the photocurable resin composition of this embodiment is 100 parts by mass.
[0060] In this embodiment, the content of antioxidant (B) in the photocurable resin composition is preferably 0.010% to 5.0% by mass, more preferably 0.050% to 4.0% by mass, even more preferably 0.10% to 3.0% by mass, even more preferably 0.30% to 2.0% by mass, and even more preferably 0.50% to 1.5% by mass, when the total amount of solids in the photocurable resin composition (total amount of components remaining as solids when cured) is taken as 100% by mass.
[0061] <Photopolymerization initiator (C)> The photocurable resin composition of this embodiment may further contain a photopolymerization initiator (C). The photopolymerization initiator (C) is not particularly limited, and known polymerization initiators can be used.
[0062] From the viewpoint of stably forming optically molded articles at low temperatures, the photopolymerization initiator (C) preferably includes a photoradical polymerization initiator. The photoradical polymerization initiator is a compound that generates radicals upon irradiation with ultraviolet or visible light. Examples of photoradical polymerization initiators include acylphosphine oxide-based initiators, oxyphenyl acetate-based initiators, benzoyl glyceride-based initiators, and hydroxyphenyl ketone-based initiators.
[0063] Examples of photopolymerization initiators (C) include benzophenone, Michlar's ketone, 4,4'-bis(diethylamino)benzophenone, xanthon, thioxanthone, isopropylxanthone, 2,4-diethylthioxanthone, 2-ethylanthraquinone, acetophenone, 2-hydroxy-2-methyl-4'-isopropylpropiophenone, isopropylbenzoin ether, isobutylbenzoin ether, 2,2-diethoxyacetophenone, 2,2-dimethoxy-2-phenylacetophenone, camphorquinone, benzantrone, 4- Ethyl dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 4,4'-di(t-butylperoxycarbonyl)benzophenone, 3,4,4'-tri(t-butylperoxycarbonyl)benzophenone, 3,3',4,4'-tetra(t-butylperoxycarbonyl)benzophenone, 3,3',4,4'-tetra(t-hexylperoxycarbonyl)benzophenone, 3,3'-di(methoxycarbonyl)-4,4'-di(t-butylperoxycarbonyl)benzophenone, 3,4'-di(methoxycarbonyl)-4,3' -di(t-butylperoxycarbonyl)benzophenone, 4,4'-di(methoxycarbonyl)-3,3'-di(t-butylperoxycarbonyl)benzophenone, 2-(4'-methoxystyryl)-4,6-bis(trichloromethyl)-s-triazine, 2-(3',4'-dimethoxystyryl)-4,6-bis(trichloromethyl)-s-triazine, 2-(2',4'-dimethoxystyryl)-4,6-bis(trichloromethyl)-s-triazine, 2-(2'-methoxystyryl)-4,6-bis(trichloromethyl)-s-triazine N, 2-(4'-pentyloxystyryl)-4,6-bis(trichloromethyl)-s-triazine, 4-[pN,N-di(ethoxycarbonylmethyl)]-2,6-di(trichloromethyl)-s-triazine, 1,3-bis(trichloromethyl)-5-(2'-chlorophenyl)-s-triazine, 1,3-bis(trichloromethyl)-5-(4'-methoxyphenyl)-s-triazine, 2-(p-dimethylaminostyryl)benzoxazole, 2-(p-dimethylaminostyryl)benzthiazole, 2-mercaptobenzothiazole, 3,3'-Carbonylbis(7-diethylaminocoumarin), 2-(o-chlorophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetrakis(4-ethoxycarbonylphenyl)-1,2'-biimidazole, 2,2'-bis(2,4-dichlorophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole, 2,2'-bis(2,4-dibromophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole 2,2'-Bis(2,4,6-trichlorophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole, 3-(2-methyl-2-dimethylaminopropionyl)carbazole, 3,6-bis(2-methyl-2-morpholinopropionyl)-9-n-dodecylcarbazole, bis(η5-2,4-cyclopentadien-1-yl)-bis(2,6-difluoro-3-(1H-pyrrole-1-yl)-phenyl)titanium, 1-hydroxycyclohexylphenyl ketone, 2-hydroxy-2-methyl-1-phenyl Phenyl-1-propanone, 1-[4-(2-hydroxyethoxy)-phenyl]-2-hydroxy-2-methyl-1-propanone, 2-hydroxy-1-{4-[4-(2-hydroxy-2-methylpropionyl)-benzyl]phenyl}-2-methyl-1-propanone, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholino-1-propanone, 2-(dimethylamino)-1-(4-morpholinophenyl)-2-benzyl-1-butanone, 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4 -(4-morpholinyl)phenyl]-1-butanone, oxy-phenyl-acetate 2-[2-oxo-2-phenylacetoxy-ethoxy]-ethyl ester, oxy-phenyl-acetate 2-[2-hydroxy-ethoxy]-ethyl ester, methyl benzoylformate, bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 2,4,6-trimethylbenzoyldiphenylphosphinic acid ester, 1-[4-(phenylthio)phenyl]-1,Examples include 2-octanedione (2-(O-benzoyl oxime)) and 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-ethanone-1-(O-acetyl oxime).
[0064] The photopolymerization initiator (C) preferably contains a hydroxyphenyl ketone-based initiator, and more preferably contains 1-hydroxycyclohexylphenyl ketone (e.g., Omnirad 184, manufactured by IGM Resins), from the viewpoint of reducing discoloration of the optically molded product.
[0065] From the viewpoint of improving the curability of the photocurable resin composition, the content of the photopolymerization initiator (C) in the photocurable resin composition of this embodiment is preferably 0.10 parts by mass or more, more preferably 0.50 parts by mass or more, even more preferably 1.0 part by mass or more, even more preferably 2.0 parts by mass or more, and even more preferably 3.0 parts by mass or more, when the content of (meth)acrylate monomer (A) in the photocurable resin composition of this embodiment is 100 parts by mass. From the viewpoint of improving the uniformity of the thickness of the photocurable resin composition during curing, the content of the photopolymerization initiator (C) in the photocurable resin composition of this embodiment is preferably 10 parts by mass or less, more preferably 8.0 parts by mass or less, even more preferably 6.0 parts by mass or less, even more preferably 5.0 parts by mass or less, and even more preferably 4.5 parts by mass or less, when the content of (meth)acrylate monomer (A) in the photocurable resin composition of this embodiment is 100 parts by mass or less. From the viewpoint of improving the curability of the photocurable resin composition and improving the uniformity of the thickness of the photocurable resin composition during curing, the content of the photopolymerization initiator (C) in the photocurable resin composition of this embodiment is preferably 0.10 parts by mass or more and 10 parts by mass or less, more preferably 0.50 parts by mass or more and 8.0 parts by mass or less, even more preferably 1.0 parts by mass or more and 6.0 parts by mass or less, even more preferably 2.0 parts by mass or more and 5.0 parts by mass or less, and even more preferably 3.0 parts by mass or more and 4.5 parts by mass or less, when the content of (meth)acrylate monomer (A) in the photocurable resin composition of this embodiment is 100 parts by mass.
[0066] In this embodiment, the content of the photopolymerization initiator (C) in the photocurable resin composition is preferably 0.10% to 10% by mass, more preferably 1.0% to 8.0% by mass, even more preferably 2.0% to 6.0% by mass, even more preferably 2.5% to 5.0% by mass, and even more preferably 3.0% to 4.5% by mass, when the total amount of solids in the photocurable resin composition (total amount of components remaining as solids when cured) is taken as 100% by mass.
[0067] <Light stabilizer (D)> The photocurable resin composition of this embodiment may further contain a light stabilizer (D). The light stabilizer (D) is not particularly limited, and known light stabilizers can be used. By including a light stabilizer (D), the photocurable resin composition can have improved color resistance.
[0068] The light stabilizer (D) preferably includes a hindered amine-based light stabilizer, from the viewpoint of improving color resistance.
[0069] Examples of hindered amine-based light stabilizers include a mixture consisting of 70% by mass of the reaction product of (1,2,2,6,6-pentamethyl-piperidine-4-yl) methacrylic acid, bis(2,2,6,6-tetramethyl-1(octyloxy)-4-piperidinyl) decandioate, 1,1-dimethylethyl hydroperoxide, and octane, and 30% by mass of polypropylene; bis(1,2,2,6,6-pentamethyl-4-piperidyl)[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methyl]butylmalonate; bis(1,2,2,6,6-pentamethyl-4-piperidyl) sebacate; and methyl-1,2,2,6,6-pentamethyl-4-piperidyl sebacate mixture. Examples include compounds, bis(2,2,6,6-tetramethyl-4-piperidyl) sebacate, tetrakis(2,2,6,6-tetramethyl-4-piperidyl)-1,2,3,4-butanetetracarboxylate, tetrakis(1,2,2,6,6-pentamethyl-4-piperidyl)-1,2,3,4-butanetetracarboxylate, mixtures of 2,2,6,6-tetramethyl-4-piperidyl-1,2,3,4-butanetetracarboxylate and tridecyl-1,2,3,4-butanetetracarboxylate, and mixtures of 1,2,2,6,6-pentamethyl-4-piperidyl-1,2,3,4-butanetetracarboxylate and tridecyl-1,2,3,4-butanetetracarboxylate.
[0070] The light stabilizer (D) preferably contains 1,2,2,6,6-pentamethyl-4-piperidyl methacrylate (e.g., ADEKA LA-82, manufactured by ADEKA Corporation) from the viewpoint of improving color resistance.
[0071] From the viewpoint of reducing discoloration of the optically molded article, the content of the light stabilizer (D) in the photocurable resin composition of this embodiment is preferably 0.0010% by mass or more, more preferably 0.0050% by mass or more, even more preferably 0.010% by mass or more, even more preferably 0.050% by mass or more, and even more preferably 0.070% by mass or more, when the total amount of solids in the photocurable resin composition (the total amount of components remaining as solids when cured) is taken as 100% by mass. From the viewpoint of reducing bleed-out, the content of the light stabilizer (D) in the photocurable resin composition of this embodiment is preferably 1.00% by mass or less, more preferably 0.60% by mass or less, even more preferably 0.50% by mass or less, even more preferably 0.40% by mass or less, and even more preferably 0.30% by mass or less, when the total amount of solids in the photocurable resin composition (the total amount of components remaining as solids when cured) is taken as 100% by mass. In this embodiment, the content of the light stabilizer (D) in the photocurable resin composition is preferably 0.0010% by mass or more and 1.00% by mass or less, more preferably 0.0050% by mass or more and 0.60% by mass or less, even more preferably 0.010% by mass or more and 0.50% by mass or less, even more preferably 0.050% by mass or more and 0.40% by mass or less, and even more preferably 0.070% by mass or more and 0.30% by mass or less, when the total amount of solids in the photocurable resin composition (total amount of components remaining as solids when cured) is taken as 100% by mass.
[0072] <Other ingredients> The photocurable resin composition may contain, as specific examples of other components besides (meth)acrylate monomer (A), polysiloxane compound (E), antioxidant (B), photopolymerization initiator (C), and light stabilizer (D), one or more selected from the group consisting of fillers, curing accelerators, plasticizers, heat stabilizers, flame retardants, antistatic agents, defoamers, silane coupling agents, ultraviolet absorbers, surfactants, and leveling agents.
[0073] <Method for producing a photocurable resin composition> The photocurable resin composition according to the present invention can be obtained by mixing a (meth)acrylate monomer (A), a polysiloxane compound (E), and other components such as an antioxidant (B), a photopolymerization initiator (C), or a light stabilizer (D) as needed, using conventionally known methods.
[0074] <Physical properties of photocurable resin compositions> Next, the physical properties of the photocurable resin composition will be described.
[0075] The contact angle between the cured film and water, prepared according to the following <Cured Film Preparation Conditions> measured in accordance with JIS R 3257:1999, will be described for the photocurable resin composition of this embodiment. In the following, the contact angle between the prepared cured film and water will also be referred to as the film contact angle.
[0076] From the viewpoint of further improving the balance between the small contact angle of the optical molded body surface and the release properties of the optical molded body, the film contact angle is preferably 90 degrees or less, more preferably 89 degrees or less, even more preferably 88 degrees or less, even more preferably 87 degrees or less, and even more preferably 86 degrees or less. The lower limit of the film contact angle is not particularly limited, but it may be 0 degrees or more, 20 degrees or more, 40 degrees or more, or 60 degrees or more.
[0077] <Conditions for preparing cured film> A 3.0mm thick, 50mm x 50mm silicone sheet (material: silicone rubber, hardness: 50 degrees) with a 35mm diameter circular hole is placed on top of a 0.7mm thick, 50mm x 50mm alkali-free glass sheet. Next, a photocurable resin composition is filled into the circular hole, and then another 0.7mm thick, 50mm x 50mm alkali-free glass sheet is placed on top of it. Next, this is placed on a SUS lab jack to adjust the height. Then, the photocurable resin composition is irradiated with 405nm wavelength LED light at 810mW for 3 minutes from above the alkali-free glass, then flipped over and irradiated with 405nm wavelength LED light at 810mW for 3 minutes. After irradiation with LED light, it is allowed to cool at 23°C for 30 minutes, and the cured photocurable resin composition is released from the alkali-free glass and silicone sheet to obtain a cured film. Here, the conditions for producing a cured film of the photocurable resin composition of this embodiment can be more specifically those described in the examples.
[0078] The film contact angle can be adjusted, for example, by adjusting the content of (meth)acrylate monomer (A), the content of polysiloxane compound (E), the blending ratio of the photocurable resin composition, the type of (meth)acrylate monomer (A), the type of polysiloxane compound (E), the types of other components, and the manufacturing conditions of the photocurable resin composition.
[0079] Regarding the photocurable resin composition of this embodiment, the contact angle between the surface of the alkali-free glass used in the above-mentioned <curing film production conditions> and water, measured in accordance with JIS R 3257:1999, will be described. In the following, the contact angle between the surface of the alkali-free glass that was in contact with the photocurable resin composition used in the above <cured film production conditions> and water will also be referred to as the glass contact angle.
[0080] From the viewpoint of reducing the transfer of components of the photocurable resin composition to the surface of alkali-free glass, the glass contact angle is preferably 75 degrees or less, more preferably 70 degrees or less, even more preferably 65 degrees or less, and even more preferably 60 degrees or less. There is no particular lower limit to the glass contact angle; for example, it may be 0 degrees or more, 20 degrees or more, 40 degrees or more, or 50 degrees or more.
[0081] The glass contact angle can be adjusted, for example, by adjusting the content of (meth)acrylate monomer (A), the content of polysiloxane compound (E), the blending ratio of the photocurable resin composition, the type of (meth)acrylate monomer (A), the type of polysiloxane compound (E), the types of other components, and the manufacturing conditions of the photocurable resin composition.
[0082] The following describes the haze value of a cured film prepared according to the above-described <Cured Film Preparation Conditions> for the photocurable resin composition of this embodiment, measured in accordance with JIS K 7136:2000, at a thickness of 3.0 mm.
[0083] From the viewpoint of improving the transparency of the optically molded article, the above haze value is preferably 1.3% or less, more preferably 1.1% or less, even more preferably 0.9% or less, even more preferably 0.7% or less, even more preferably 0.5% or less, even more preferably 0.3% or less, even more preferably 0.2% or less, and even more preferably 0.1% or less. The lower limit of the above haze value is not particularly restricted, but it may be, for example, 0.01% or higher, 0.03% or higher, or 0.05% or higher.
[0084] The above haze value can be adjusted, for example, by adjusting the content of (meth)acrylate monomer (A), the content of polysiloxane compound (E), the blending ratio of the photocurable resin composition, the type of (meth)acrylate monomer (A), the type of polysiloxane compound (E), the types of other components, and the manufacturing conditions of the photocurable resin composition. More specifically, the method for measuring the haze value can be the method described in the examples.
[0085] <Applications of photocurable resin compositions> Next, we will explain the applications of the photocurable resin composition.
[0086] The photocurable resin composition of this embodiment can improve the balance between the small contact angle of the surface of the optically molded body formed from the photocurable resin composition and the release properties of the optically molded body. Therefore, it can be used in methods for forming optically molded bodies such as injection molding, compression molding, injection compression molding, extrusion molding, solution casting, and casting. In particular, the photocurable resin composition of this embodiment can be used in the casting method.
[0087] The photocurable resin composition of this embodiment can improve the balance between the small contact angle of the surface of the optically molded body molded from the photocurable resin composition and the release properties of the optically molded body. Therefore, the applications of the optically molded body molded from the photocurable resin composition are not particularly limited and can be used in a variety of applications.
[0088] The photocurable resin composition of this embodiment can, for example, preferably be used in lenses. The lens may include one or more types selected from the group consisting of spherical lenses, aspherical lenses, biconvex lenses, plano-convex lenses, convex meniscus lenses, biconcave lenses, plano-concave lenses, concave meniscus lenses, etc.
[0089] The photocurable resin composition of this embodiment can be used, for example, more preferably, in one or more lenses selected from the group consisting of virtual reality lenses (VR lenses), mixed reality lenses (MR lenses), augmented reality lenses (AR lenses), cross-reality lenses (xR lenses), and head-mounted display lenses (HMD lenses).
[0090] The photocurable resin composition of this embodiment can, for example, preferably be used in a display cover (hereinafter also referred to as a cover display). The cover display includes, for example, one or more types selected from the group consisting of a front cover display and a full cover display.
[0091] The photocurable resin composition of this embodiment can be used, for example, more preferably, in one or more cover displays selected from the group consisting of virtual reality cover displays (VR cover displays), mixed reality cover displays (MR cover displays), augmented reality cover displays (AR cover displays), cross-reality cover displays (xR cover displays), and head-mounted display cover displays (HMD cover displays).
[0092] (optical molded body) The optically molded article of this embodiment includes a cured product of the photocurable resin composition of this embodiment. The optically molded article of this embodiment can be manufactured using the photocurable resin composition of this embodiment. The optically molded article can be manufactured from the photocurable resin composition of this embodiment by any method such as injection molding, compression molding, injection compression molding, extrusion molding, solution casting, and casting.
[0093] The optically molded body of this embodiment includes a lens. The lens includes, for example, one or more types selected from the group consisting of spherical lenses, aspherical lenses, biconvex lenses, plano-convex lenses, convex meniscus lenses, biconcave lenses, plano-concave lenses, concave meniscus lenses, etc.
[0094] The lens of this embodiment includes one or more types selected from the group consisting of virtual reality lenses (VR lenses), mixed reality lenses (MR lenses), augmented reality lenses (AR lenses), cross-reality lenses (xR lenses), and head-mounted display lenses (HMD lenses).
[0095] The optically molded body of this embodiment includes a display cover (cover display). The cover display includes, for example, one or more types selected from the group consisting of a front cover display and a full cover display.
[0096] The cover display of this embodiment includes one or more types selected from the group consisting of virtual reality cover displays (VR cover displays), mixed reality cover displays (MR cover displays), augmented reality cover displays (AR cover displays), cross-reality cover displays (xR cover displays), and head-mounted display cover displays (HMD cover displays).
[0097] The maximum thickness of an optically molded body is the portion of the optically molded body where the thickness of the optical component is greatest. The location of the maximum thickness of the optically molded body is not particularly limited and can be set as appropriate depending on the application.
[0098] For example, the maximum thickness of the optically molded body in this embodiment is preferably 0.01 mm or more, more preferably 0.1 mm or more, even more preferably 0.5 mm or more, even more preferably 1.0 mm or more, even more preferably 2.0 mm or more, even more preferably 3.0 mm or more, even more preferably 4.0 mm or more, and even more preferably 5.0 mm or more.
[0099] For example, the maximum thickness of the optically molded body in this embodiment is preferably 20.0 mm or less, more preferably 19.9 mm or less, even more preferably 19.8 mm or less, even more preferably 19.5 mm or less, even more preferably 18.0 mm or less, even more preferably 17.0 mm or less, even more preferably 16.0 mm or less, and even more preferably 15.0 mm or less.
[0100] For example, the maximum thickness of the optically molded body in this embodiment is preferably 0.01 mm or more and 20.0 mm or less, more preferably 0.1 mm or more and 19.9 mm or less, even more preferably 0.5 mm or more and 19.8 mm or less, even more preferably 1.0 mm or more and 19.5 mm or less, even more preferably 2.0 mm or more and 19.0 mm or less, even more preferably 3.0 mm or more and 18.0 mm or less, even more preferably 4.0 mm or more and 17.0 mm or less, even more preferably 5.0 mm or more and 16.0 mm or less, and even more preferably 5.0 mm or more and 15.0 mm or less.
[0101] Furthermore, the photocurable resin composition of this embodiment can improve the balance between the small contact angle on the surface of the optically molded body and the release properties of the optically molded body, and is therefore applicable to optically molded bodies with a thickness of 0.01 mm or more.
[0102] The embodiments of the present invention have been described above, but these are merely examples, and various other configurations can also be adopted. Furthermore, the present invention is not limited to the embodiments described above, and any modifications, improvements, etc., that do not impair the effects of the present invention are included in the present invention. [Examples]
[0103] This embodiment will be described in detail below with reference to examples and other relevant information. However, this embodiment is not limited in any way to the descriptions of these examples.
[0104] First, the materials used in each example are listed. • (Meth)acrylate monomer (A) (Meth)acrylate monomer 1: Alicyclic monofunctional (meth)acrylate monomer (dicyclopentanyl methacrylate, manufactured by Kokusei Chemical Co., Ltd.) (hereinafter also referred to as GM81HDA). (Meth)acrylate monomer 2: Linear bifunctional (meth)acrylate monomer (1,12-dodecanediol dimethacrylate, manufactured by Shin-Nakamura Chemical Industry Co., Ltd.) (hereinafter also referred to as DDD).
[0105] (E) Polysiloxane compound having a (meth)acryloyl group Polysiloxane compound 1:X-22-2404 (manufactured by Shin-Etsu Chemical Co., Ltd.) (A polysiloxane compound having a methacryloyl group at one end and a methyl group at the other; molecular weight calculated from functional group equivalents: 420 g / mol) Polysiloxane compound 2: X-22-174ASX (manufactured by Shin-Etsu Chemical Co., Ltd.) (A polysiloxane compound having a methacryloyl group at one end and a methyl group at the other; molecular weight calculated from functional group equivalents: 900 g / mol) Polysiloxane compound 3: X-22-164AS (manufactured by Shin-Etsu Chemical Co., Ltd.) (a polysiloxane compound with methacryloyl groups at both ends; molecular weight calculated from functional group equivalents: 900 g / mol) Polysiloxane compound 4:X-22-2426 (manufactured by Shin-Etsu Chemical Co., Ltd.) (a polysiloxane compound having a methacryloyl group at one end and a methyl group at the other; molecular weight calculated from functional group equivalents: 12,000 g / mol) • Polysiloxane compounds that do not have a (meth)acryloyl group Polysiloxane compound 5: KF-96-20cs (manufactured by Shin-Etsu Chemical Co., Ltd.) (a polysiloxane compound having methyl groups at both ends) Polysiloxane compound 6: KF-640 (manufactured by Shin-Etsu Chemical Co., Ltd.) (a polysiloxane compound with methyl groups at both ends)
[0106] <Method for calculating molecular weight from functional group equivalents> • Polysiloxane compounds 1-2, 4 The molecular weight calculated from the functional group equivalent is obtained from the following formula (4) for polysiloxane compounds (polysiloxane compound (E1)) that have one (meth)acryloyl group in the molecule. Equation (4): [Molecular weight of polysiloxane compound (E1) calculated from functional group equivalent (g / mol)] = [Functional group equivalent of polysiloxane compound (E1) (g / mol)] • Polysiloxane compound 3 The molecular weight calculated from the functional group equivalents is obtained from the following formula (5) for polysiloxane compounds (polysiloxane compound (E2)) that have two (meth)acryloyl groups in the molecule. Equation (5): [Molecular weight of polysiloxane compound (E2) calculated from functional group equivalent (g / mol)] = [Functional group equivalent of polysiloxane compound (E2) (g / mol)] × 2 The functional group equivalents for polysiloxane compounds 1-4 were based on catalog values from Shin-Etsu Chemical Co., Ltd.
[0107] • Antioxidant (B) Antioxidant 1: Thioether-based antioxidant (bis[3-(dodecylthio)propionic acid]2,2-bis[[3-(dodecylthio)-1-oxopropyloxy]methyl]-1,3-propanediyl, manufactured by ADEKA Corporation, product name: ADEKA Stab AO-412S) (hereinafter also referred to as AO-412S) Antioxidant 2: Phenolic antioxidant (Pentaerythritol tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], manufactured by ADEKA Corporation, product name: ADEKA Stab AO-60) (hereinafter also referred to as AO-60) • Photopolymerization initiator (C) Photopolymerization initiator 1: Photoradical polymerization initiator (1-hydroxycyclohexylphenyl ketone, manufactured by IGM Resins, product name: Omnirad 184) • Light stabilizer (D) Light stabilizer 1: Hindered amine light stabilizer (1,2,2,6,6-pentamethyl-4-piperidyl methacrylate, manufactured by ADEKA Corporation, product name: ADEKA Stab LA-82) (hereinafter also referred to as LA-82)
[0108] (Examples 1-6, Comparative Examples 1-3) A liquid photocurable resin composition was obtained by blending each component to achieve the composition shown in Table 1. The units for the composition in Table 1 are parts by mass. The physical properties of the optically molded articles obtained from the photocurable resin compositions of each example were measured by the following method. The measurement results are shown in Table 1.
[0109] <Method for measuring the contact angle between cured film and water> For each example of a photocurable resin composition, a cured film was prepared according to the <Conditions for Cured Film Preparation> described below. Next, the contact angle between the prepared cured film and water (film contact angle) was measured in accordance with JIS R 3257:1999, with a sample size of n=5. The average value calculated from the measured values was defined as the film contact angle. A contact angle meter (product name: DMo-0902, manufactured by Kyowa Interface Science Co., Ltd.) was used to measure the film contact angle.
[0110] <Conditions for preparing cured film> A 3.0mm thick, 50mm x 50mm silicone sheet (material: silicone rubber, hardness: 50 degrees) with a 35mm diameter circular hole was placed on top of a 0.7mm thick, 50mm x 50mm alkali-free glass sheet (product name: JIS R 3202, glass plate with a thin edge, manufactured by Test Piece Co., Ltd.). After filling the circular hole in the silicone sheet with a photocurable resin composition, another 0.7mm thick, 50mm x 50mm alkali-free glass sheet (product name: JIS R 3202, glass plate with a thin edge, manufactured by Test Piece Co., Ltd.) was placed on top. At this time, it was confirmed that there were no air bubbles. Hereinafter, the above-described structure, in which a silicone sheet is placed on top of alkali-free glass, the circular hole in the silicone sheet is filled with a photocurable resin composition, and then another alkali-free glass sheet is placed on top, may be referred to as a laminate. The laminate described above was placed on a stainless steel lab jack, and the height of the stainless steel lab jack was adjusted. From above the alkali-free glass, the photocurable resin composition was irradiated with 405nm LED light at 810mW for 3 minutes using an LED light irradiation device (CCS Corporation, product name: 405nm-120mm air-cooled batch type irradiation device, model number: HLDL-120505-NWPSC). Then, the laminate was turned over and irradiated again with 405nm LED light at 810mW for another 3 minutes. After irradiation with LED light, the laminate was allowed to cool at 23°C for 30 minutes. After cooling, the cured product of the photocurable resin composition was released from the alkali-free glass and silicone sheet to obtain a cured film of the photocurable resin composition. The LED light intensity was measured using an ultraviolet integrated light meter (product name: UIT-250, manufactured by Ushio Inc.).
[0111] <Method for measuring the contact angle between glass and water> For each example of the photocurable resin composition, the contact angle (glass contact angle) between the surface in contact with the alkali-free glass photocurable resin composition used in the above <curing film production conditions> and water was measured in accordance with JIS R 3257:1999, with a sample size of n=5. The average value calculated from the measured values was defined as the glass contact angle. A contact angle meter (product name: DMo-0902, manufactured by Kyowa Interface Science Co., Ltd.) was used to measure the glass contact angle.
[0112] <Method for measuring haze value> For each example of a photocurable resin composition, the haze value of the cured film prepared according to the above <Cured Film Preparation Conditions> was measured at a thickness of 3.0 mm in accordance with JIS K 7136:2000.
[0113] <Turbidity Evaluation> For each example of the photocurable resin composition, a cured film was prepared according to the above <Conditions for preparing cured film>. Next, the prepared cured film was immersed in benzyl alcohol at 25°C. Then, the haze value (haze value during benzyl alcohol immersion) of the cured film immersed in benzyl alcohol at a thickness of 3.0 mm was measured in accordance with JIS K 7136:2000. The haze value during benzyl alcohol immersion was evaluated as A if it was less than 1.0%, and as B if it was 1.0% or more.
[0114] <Evaluation of mold release properties> Optical molded bodies were fabricated using the photocurable resin compositions of each example, according to the following <Optical Molded Body Fabrication Conditions>. After cooling, the release properties of the optical molded bodies were evaluated by pulling up the spherical plano-convex lens. This evaluation was performed under conditions with a sample size of n=15. The number of samples that could be peeled from the mold was evaluated as follows: A if it was 15, B if it was between 12 and 14, and C if it was 11 or less.
[0115] <Conditions for manufacturing optically molded bodies> A mold was prepared by forming a circular recess with a depth of 8.0 mm and a diameter of 40 mm in a 15 mm thick, 60 mm x 60 mm SUS304 plate. After filling the circular recess with a photocurable resin composition, a spherical plano-convex lens (product name: SLB-60-70P, manufactured by Sigma Koki Co., Ltd.) was placed on top. At this time, it was confirmed that there were no air bubbles. Hereafter, the structure in which the circular recess of the mold described above is filled with a photocurable resin composition and the spherical plano-convex lens is placed on top may be referred to as laminate 2. The laminate 2 described above was placed on a stainless steel lab jack, and the height of the stainless steel lab jack was adjusted. From above the spherical plano-convex lens, the photocurable resin composition was irradiated with 405nm LED light at 810mW for 5 minutes using an LED light irradiation device (manufactured by CCS, product name: 405nm-120mm air-cooled batch irradiation device, model number: HLDL-120505-NWPSC). After that, the laminate 2 was allowed to cool at 23°C for 30 minutes. After cooling, an optically molded body of the photocurable resin composition was obtained, positioned between the mold and the spherical plano-convex lens. The LED light intensity was measured using an ultraviolet integrated light meter (product name: UIT-250, manufactured by Ushio Inc.).
[0116] [Table 1]
Claims
1. A photocurable resin composition that can be used in optically molded articles, It comprises a (meth)acrylate monomer and a polysiloxane compound, The (meth)acrylate monomer comprises a (meth)acrylate monomer with two or more functionalities, The polysiloxane compound is a photocurable resin composition having a (meth)acryloyl group.
2. The photocurable resin composition according to claim 1, wherein the molecular weight calculated from the functional group equivalent of the polysiloxane compound is 200 g / mol or more and 5,000 g / mol or less.
3. The photocurable resin composition according to claim 1 or 2, wherein the content of the polysiloxane compound is 0.005 parts by mass or more and 10 parts by mass or less, when the content of the (meth)acrylate monomer is 100 parts by mass.
4. The photocurable resin composition according to any one of claims 1 to 3, wherein the bifunctional or more (meth)acrylate monomer comprises one or more selected from the group consisting of alicyclic bifunctional (meth)acrylate monomers and linear bifunctional (meth)acrylate monomers.
5. The photocurable resin composition according to claim 4, wherein the total content of the alicyclic bifunctional (meth)acrylate monomer and the linear bifunctional (meth)acrylate monomer is 60 parts by mass or more and 100 parts by mass or less, when the total content of the bifunctional or more (meth)acrylate monomers is 100 parts by mass.
6. The photocurable resin composition according to any one of claims 1 to 5, wherein the content of the bifunctional or more (meth)acrylate monomer is 5 parts by mass or more and 100 parts by mass or less when the total content of the (meth)acrylate monomer is 100 parts by mass.
7. The photocurable resin composition according to any one of claims 1 to 6, wherein the (meth)acrylate monomer further comprises a monofunctional (meth)acrylate monomer.
8. The photocurable resin composition according to claim 7, wherein the monofunctional (meth)acrylate monomer has an alicyclic skeleton.
9. A photocurable resin composition according to any one of claims 1 to 8, wherein the contact angle between the cured film and water, measured in accordance with the following <cured film production conditions> as measured in accordance with JIS R 3257:1999, is 90 degrees or less. <Conditions for preparing cured film> A 3.0 mm thick, 50 mm x 50 mm silicone sheet (material: silicone rubber, hardness: 50 degrees) with a 35 mm diameter circular hole is placed on a 0.7 mm thick, 50 mm x 50 mm alkali-free glass sheet. The photocurable resin composition is then filled into the circular hole. Another 0.7 mm thick, 50 mm x 50 mm alkali-free glass sheet is placed on top of the silicone sheet. The height is adjusted using a stainless steel lab jack. The photocurable resin composition is then irradiated with 405 nm wavelength LED light at 810 mW for 3 minutes from above the alkali-free glass sheet. After that, it is turned over and irradiated with 405 nm wavelength LED light at 810 mW for 3 minutes. Finally, it is allowed to cool at 23°C for 30 minutes to release the cured product of the photocurable resin composition from the alkali-free glass and the silicone sheet to obtain a cured film.
10. A photocurable resin composition according to any one of claims 1 to 9, wherein the haze value of a cured film prepared according to the following <cured film preparation conditions>, measured in accordance with JIS K 7136:2000, is 1.3% or less at a thickness of 3.0 mm. <Conditions for preparing cured film> A 3.0 mm thick, 50 mm x 50 mm silicone sheet (material: silicone rubber, hardness: 50 degrees) with a 35 mm diameter circular hole is placed on a 0.7 mm thick, 50 mm x 50 mm alkali-free glass sheet. The photocurable resin composition is then filled into the circular hole. Another 0.7 mm thick, 50 mm x 50 mm alkali-free glass sheet is placed on top of the silicone sheet. The height is adjusted using a stainless steel lab jack. The photocurable resin composition is then irradiated with 405 nm wavelength LED light at 810 mW for 3 minutes from above the alkali-free glass sheet. After that, it is turned over and irradiated with 405 nm wavelength LED light at 810 mW for 3 minutes. Finally, it is allowed to cool at 23°C for 30 minutes to release the cured product of the photocurable resin composition from the alkali-free glass and the silicone sheet to obtain a cured film.
11. A photocurable resin composition according to any one of claims 1 to 10, further comprising an antioxidant.
12. A photocurable resin composition according to any one of claims 1 to 11, further comprising a photopolymerization initiator.
13. The photocurable resin composition according to claim 12, wherein the photopolymerization initiator comprises a photoradical polymerization initiator.
14. A photocurable resin composition according to any one of claims 1 to 13, further comprising a light stabilizer.
15. A photocurable resin composition according to any one of claims 1 to 14, which can be used in a casting method.
16. A photocurable resin composition according to any one of claims 1 to 15, which can be used for one or more lenses selected from the group consisting of virtual reality lenses (VR lenses), mixed reality lenses (MR lenses), augmented reality lenses (AR lenses), cross-reality lenses (xR lenses), and head-mounted display lenses (HMD lenses).
17. An optically molded article comprising a cured product of a photocurable resin composition according to any one of claims 1 to 16.
18. The optical molded body according to claim 17, wherein the optical molded body includes a lens.
19. The optical molded body according to claim 18, wherein the lens includes one or more selected from the group consisting of virtual reality lenses (VR lenses), mixed reality lenses (MR lenses), augmented reality lenses (AR lenses), cross-reality lenses (xR lenses), and head-mounted display lenses (HMD lenses).
20. The optical molded body according to claim 17, wherein the optical molded body includes a cover display.
21. The optical molded body according to claim 20, wherein the cover display includes one or more selected from the group consisting of a cover display for virtual reality, a cover display for mixed reality, a cover display for augmented reality, a cover display for cross-reality, and a cover display for a head-mounted display.
Citation Information
Patent Citations
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