Thermally curable lens composition, thermally cured lens and method for manufacturing the same

Abstract

The present application relates to a thermally cured lens composition, a thermally cured lens and a manufacturing method thereof. The thermally cured lens is manufactured by using a thermally cured lens composition containing a plurality of (meth)acrylate monomers in a specific ratio and a thermal initiator, and then performing a thermal curing step. In this way, the thermally cured lens is not only suitable for the specification of a thermally cured acrylic lens of 1.50, but also has high manufacturing process stability, which can reduce production risk and cost. The obtained thermally cured lens has better heat resistance and high Abbe number.

Description

Technical Field

[0001] This invention relates to a thermosetting lens composition, a thermosetting lens, and a method for manufacturing the same, particularly to a thermosetting lens composition, a thermosetting lens, and a method for manufacturing the same that have high process safety, good decoction properties, good heat resistance, and a high Abbe number. Background Technology

[0002] Due to the evolution and development of technological products, there is a huge market demand for both resin and glass lenses. Lenses are needed in everything from eyeglass lenses to optical drive heads and camera lenses. Common resin lenses include polycarbonate (PC) lenses, PMMA resin lenses, and thermosetting resin lenses (such as the trade name CR-39).

[0003] PC lenses, or polycarbonate, are thermoplastic materials. This material boasts high heat resistance, resistance to oils, greases, and acids, low water absorption, and high dimensional stability, making it a truly safe lens. However, PC lenses also have drawbacks: they are not scratch-resistant, have poor chemical resistance, are prone to stress and cracking, have poor compatibility with other resins, and exhibit significant chromatic aberration at high prescriptions.

[0004] PMMA lenses are made of thermoplastic resin, primarily polymethyl methacrylate, commonly known as acrylic glass, and are lightweight and inexpensive. However, PMMA lenses suffer from drawbacks such as easy deformation under heat, poor abrasion resistance, poor chemical resistance, poor impact resistance, and poor curvature stability. Therefore, PMMA lenses are currently mostly used in low-end sunglasses.

[0005] CR-39 lenses are a representative example of thermosetting resin lenses. CR-39 lenses offer advantages such as good chemical stability, low specific gravity, low dispersion, excellent light transmittance, adjustable refractive index, ease of processing, and resistance to fading after dyeing. However, their abrasion resistance and impact resistance are relatively poor. Currently, the most commonly used initiator for producing CR-39 (Dially Glycol Carbonates) is IPP (diisopropyl peroxydicarbonate). However, IPP requires low-temperature storage (-10°C) and is highly prone to explosion during polymerization, thus raising concerns about process safety.

[0006] In view of this, the present invention provides a thermosetting lens with high process safety, good decoction properties, good heat resistance and high Abbe number, so as to effectively solve the problems existing in the prior art. Summary of the Invention

[0007] The purpose of this invention is to provide a thermosetting lens composition with advantages such as high process safety, good decoctionability, good heat resistance and high Abbe number, to overcome the shortcomings of prior art; and thermosetting lenses manufactured using this composition.

[0008] In a first aspect of the invention, a thermosetting lens composition is provided, comprising:

[0009] Component a) at least one of a monofunctional (meth)acrylate monomer and a polyfunctional (meth)acrylate monomer;

[0010] Component b) at least two di(meth)acrylate monomers having alkyl ether groups;

[0011] Component c) Polyurethane acrylate monomer;

[0012] Component d) chain transfer agent, wherein the chain transfer agent does not contain diene chain transfer agents; and

[0013] Component e) Thermal initiator,

[0014] The at least one of the components b) is selected from bisphenol A polyalkyl ether di(meth)acrylate monomer; wherein, based on a total usage of 100 parts by weight of the thermosetting lens composition, the usage of the bisphenol A polyalkyl ether di(meth)acrylate monomer is 5-40 parts by weight (preferably 10-25 parts by weight, more preferably 15-23 parts by weight).

[0015] In another preferred embodiment, the viscosity of the thermosetting lens composition is less than 150 cps.

[0016] In another preferred embodiment, the thermosetting lens composition, wherein the proportions of each component are as follows, based on a total usage of 100 parts by weight of the thermosetting lens composition:

[0017] The amount of monofunctional (meth)acrylate monomer used in component a) is 5-60 parts by weight (preferably 10-50 parts by weight, more preferably 15-40 parts by weight);

[0018] The amount of the polyfunctional (meth)acrylate monomer used in component a) is 0-30 parts by weight (preferably 1-15 parts by weight, more preferably 2-5 parts by weight);

[0019] The amount of the di(meth)acrylate monomer having an alkyl ether group in component b) is 10-90 parts by weight (preferably 20-80 parts by weight, more preferably 30-70 parts by weight);

[0020] The amount of component c) used is 3-80 parts by weight (preferably 5-50 parts by weight, more preferably 10-30 parts by weight);

[0021] The amount of component d) used is 0.05-10 parts by weight (preferably 0.1-5 parts by weight).

[0022] The amount of component e) used is 0.05-5 parts by weight (preferably 0.1-1 parts by weight).

[0023] In another preferred embodiment, the thermosetting lens composition wherein the monofunctional (meth)acrylate monomer is used in an amount of 15-35 parts by weight.

[0024] In another preferred embodiment, the composition comprises 15-35 wt% of the monofunctional (meth)acrylate monomer based on the total weight of the composition.

[0025] In another preferred embodiment, the thermosetting lens composition wherein the alkyl ether (EO) equivalent number of the composition is between 2.1 and 8 (preferably between 2.2 and 5, more preferably between 2.3 and 4).

[0026] In another preferred embodiment, the thermosetting lens composition has one or more features selected from the group consisting of:

[0027] 1) For component b), in addition to containing the bisphenol A polyalkyl ether di(meth)acrylate monomer, it also contains a substance selected from the group consisting of: 3-hydroxy-2,2-dimethylpropionic acid 3-hydroxy-2,2-dimethylpropyl diacrylate, 1,6-hexanediol diacrylate, ethoxylated 1,6-hexanediol diacrylate, dipropylene glycol diacrylate, tricyclodecanediethanol diacrylate, ethoxylated dipropylene glycol diacrylate, neopentyl glycol diacrylate, propionyl neopentyl glycol diacrylate, ethoxylated bisphenol A. Dimethacrylate, 2-methyl-1,3-propanediol diacrylate, ethoxylated-2-methyl-1,3-propanediol diacrylate, 2-butyl-2-ethyl-1,3-propanediol diacrylate, ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, tripropylene glycol dimethacrylate, 1,4-butanediol dimethacrylate, 1,6-hexanediol dimethacrylate, allylated cyclohexyl dimethacrylate, polyethylene glycol diacrylates with an EO number of 1 to 20, or combinations thereof;

[0028] 2) The monofunctional (meth)acrylate monomer in component a) is selected from the group consisting of: methyl methacrylate, butyl methacrylate, 2-phenoxyethyl acrylate, ethoxylated 2-phenoxyethyl acrylate, 2-(2-ethoxyethoxy)ethyl acrylate, cyclotrimethylolpropane methyl acetal acrylate, β-carboxyethyl acrylate, 3,3,5-trimethylcyclohexyl acrylate, o-phenylphenoxyethyl acrylate, 2-(p-isopropylphenyl-phenoxy)-ethyl acrylate, methyl laurate, isooctyl acrylate, methyl stearate, isodecyl acrylate, isobornyl methacrylate, benzyl acrylate, 2-hydroxyethyl methacrylate phosphate, caprolactone acrylate, hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, or combinations thereof;

[0029] 3) The polyfunctional (meth)acrylate monomer in component a) has three or more functional groups, and the polyfunctional (meth)acrylate monomer is selected from the group consisting of: tris(2-hydroxyethyl)isocyanurate triacrylate, pentaerythritol triacrylate, ethoxylated trimethylolpropane triacrylate, propoxylated trimethylolpropane triacrylate, trimethylolpropane trimethacrylate, pentaerythritol tetraacrylate, ethoxylated pentaerythritol tetraacrylate, bis-trimethylolpropane tetraacrylate, propoxylated pentaerythritol tetraacrylate, dipentaerythritol hexaacrylate, ethoxylated trimethylolpropane trimethacrylate, propoxylated glycerol trimethacrylate, propoxylated glycerol triacrylate, tri(propyleneoxyethyl)isocyanurate, trimethylolpropane triacrylate, or combinations thereof;

[0030] 4) For component b), the bisphenol A polyalkyl ether di(meth)acrylate monomer is selected from the group consisting of: bisphenol A dimethacrylate, ethoxylated bisphenol A diacrylate, and ethoxylated bisphenol A dimethacrylate;

[0031] 5) Component c) is selected from the following group: diacrylate isocyanurate, dimethacrylate isocyanurate, triacrylate isocyanurate and polyurethane diacrylate and combinations thereof;

[0032] 6) Component e) is selected from the group consisting of: benzene peroxide, cumene hydroperoxide, dicumene peroxide, tert-butyl hydroperoxide, tert-butyl maleic acid peroxide, diacetyl peroxide, lauroyl peroxide, a mixture of one or more of the above peroxides with an amino acid or sulfonic acid, a mixture of one or more of the above peroxides with a cobalt-containing compound, azobisisobutyronitrile, azobisisoheptanenitrile, and combinations thereof.

[0033] In another preferred embodiment, component e) is selected from the group consisting of azobisisobutyronitrile, azobisisoheptanenitrile, and combinations thereof.

[0034] In another preferred embodiment, component d) is a well-known chain transfer agent with a specific functional group, but not a diene chain transfer agent.

[0035] In another preferred embodiment, component d) is selected from the group consisting of chain transfer agents having a carboxyl group, chain transfer agents having a hydroxyl group, chain transfer agents having an alkyl group, polyfunctional thiol compounds, and the like.

[0036] In another preferred embodiment, the chain transfer agent having a carboxyl group includes, but is not limited to, thioglycolic acid.

[0037] In another preferred embodiment, the chain transfer agent having a hydroxyl group includes, but is not limited to, mercaptobutanol.

[0038] In another preferred embodiment, the alkyl chain transfer agent includes, but is not limited to, dodecyl mercaptan.

[0039] In another preferred embodiment, the polyfunctional thiol compound includes, but is not limited to, heterocyclic compounds with a thiol group such as pentaerythritol tetra(thioglycolate) or dipentaerythritol hexa(thioglycolate).

[0040] In another preferred embodiment, the monofunctional (meth)acrylate monomer includes, but is not limited to, methyl methacrylate, methyl laurate, butyl methacrylate, caprolactone acrylate, hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, or combinations thereof.

[0041] In another preferred embodiment, monofunctional (meth)acrylate monomers and polyfunctional (meth)acrylate monomers may be added selectively or in combination as needed.

[0042] In another preferred embodiment, the thermosetting lens composition does not contain polyfunctional (meth)acrylate monomers.

[0043] In another preferred embodiment, both monofunctional (meth)acrylate monomers and polyfunctional (meth)acrylate monomers are present, and the total amount of both is preferably between about 5-70 parts by weight, more preferably between 5-30 parts by weight, based on a total usage of 100 parts by weight in the thermosetting lens composition.

[0044] In another preferred embodiment, the bisphenol A polyalkyl ether di(meth)acrylate monomer is an ethoxylated functionalized di(meth)acrylate monomer, and its EO equivalent number is between 2 and 20, preferably between 2 and 15, and more preferably between 3 and 10.

[0045] In another preferred embodiment, the refractive index of the composition is ≥1.48, more preferably ≥1.50, and even more preferably ≥1.51.

[0046] In another preferred embodiment, component c) is isocyanurate dimethacrylate or polyurethane diacrylate.

[0047] In another preferred embodiment, the thermosetting lens composition further comprises an additive selected from the group consisting of dyes, antioxidants, heat stabilizers, dispersants, release agents, wetting agents, defoamers, anti-yellowing agents, ultraviolet absorbers, or combinations thereof.

[0048] In another preferred embodiment, the ultraviolet absorber includes, but is not limited to, benzotriazoles, benzotriazines, benzophenones, or salicylic acid derivatives.

[0049] In another preferred embodiment, the additive is free of solvents, fluorine, styrene monomers (e.g., styrene, methylstyrene, and divinylbenzene), styrene copolymers, or microparticles.

[0050] In another preferred embodiment, the amount of additive used is between about 0.05 parts by weight and 2 parts by weight, based on a total of 100 parts by weight of the thermosetting lens composition.

[0051] In a second aspect of the present invention, a method for manufacturing a thermosetting lens is provided, which utilizes the thermosetting lens composition as described in the first aspect of the present invention, specifically comprising the following steps:

[0052] S1. The thermosetting lens composition is mixed into an adhesive solution according to the proportions described in the first aspect of the present invention, and then vacuum defoamed to form a first mixture;

[0053] S2. The first mixture is injected into a light-transmitting mold to form a mold body, and the mold body is heated to form a second mixture;

[0054] S3. The second mixture is cured under controlled temperature to form a thermosetting lens;

[0055] S4. Demold and dry the thermosetting lens from S3, and then cure it a second time to obtain the thermosetting lens.

[0056] In another preferred embodiment, the vacuum defoaming described in S1 is carried out for 30 minutes at room temperature and a pressure of less than 0.1 torr.

[0057] In another preferred embodiment, a demolding step may be added after the second mixture is formed;

[0058] In another preferred embodiment, edge grinding, cleaning, and secondary curing steps can be optionally added after the above demolding step.

[0059] In another preferred embodiment, the machine used for demolding is a manual stamping machine.

[0060] In another preferred embodiment, the drying operation is carried out in an oven at 100°C for one hour.

[0061] In a third aspect of the invention, a thermosetting lens is provided, which is made from the thermosetting lens composition described in the first aspect of the invention.

[0062] In another preferred embodiment, the thermosetting lens has a refractive index between 1.48 and 1.52.

[0063] In another preferred embodiment, the thermosetting lens has a light transmittance of ≥92%.

[0064] In another preferred embodiment, the thermosetting lens has a specific gravity of ≤1.2 mg / mL.

[0065] In another preferred embodiment, the thermosetting lens has a pencil hardness of ≥1H.

[0066] In another preferred embodiment, the Abbe number of the thermosetting lens is >49.

[0067] In another preferred embodiment, the Abbe number of the thermosetting lens is 49-60.

[0068] It should be understood that, within the scope of this invention, the above-described technical features of this invention and the technical features specifically described below (such as in the embodiments) can be combined with each other to form new or preferred technical solutions. Due to space limitations, they will not be described in detail here. Detailed Implementation

[0069] Through extensive and in-depth research, the inventors of this invention have developed a thermosetting lens with high process safety, excellent release properties, good heat resistance, and a high Abbe number by adjusting the composition and properties of the thermosetting lens composition (such as the EO equivalent number of the composition). Based on this, the present invention was completed.

[0070] the term

[0071] To facilitate understanding of the disclosures presented herein, several terms are defined below.

[0072] The term “about” refers to the acceptable error of a particular value as determined by a person skilled in the art, depending on how the value is measured or determined.

[0073] The term "Abbe number" is a value used to measure the degree of light dispersion in a medium.

[0074] It should be understood that, for the purposes of this invention, for a single component (such as component b), the EO equivalent number refers to the number of alkyl ether groups (EO) contained in one monomer molecule; for a composition, the EO equivalent number refers to the value calculated according to Formula I.

[0075] Thermosetting lens composition

[0076] As mentioned above, the present invention provides a thermosetting lens and a method for manufacturing the same. The method utilizes a thermosetting lens composition containing a specific proportion of various (meth)acrylate monomers and a thermal initiator to perform a thermosetting step, thereby producing a thermosetting lens with higher hardness and better impact resistance at a lower process cost.

[0077] The thermosetting lens composition of the present invention,

[0078] Component a) at least one of a monofunctional (meth)acrylate monomer and a polyfunctional (meth)acrylate monomer;

[0079] Component b) at least two di(meth)acrylate monomers having alkyl ether groups;

[0080] Component c) Polyurethane acrylate monomer;

[0081] Component d) chain transfer agent, wherein the chain transfer agent does not contain diene chain transfer agents; and

[0082] Component e) Thermal initiator,

[0083] At least one of the components b) is selected from bisphenol A polyalkyl ether di(meth)acrylate monomers.

[0084] Wherein, based on a total usage of 100 parts by weight of the thermosetting lens composition, the usage of the bisphenol A polyalkyl ether di(meth)acrylate monomer is 5-40 parts by weight (preferably 10-25 parts by weight, more preferably 15-23 parts by weight).

[0085] In the thermosetting lens composition of the present invention, the monofunctional (meth)acrylate monomer can adjust the viscosity of the thermosetting lens composition, giving it low viscosity and resulting in lenses with low refractive index, high Abbe number, and low shrinkage. This effectively reduces viscosity and related properties, and facilitates operations such as venting and pouring into lens molds.

[0086] When the amount of monofunctional (meth)acrylate monomer used is too high (e.g., above 25 parts by weight, especially above 30 parts by weight), the curing rate of the thermosetting lens composition will be slowed down, easily leading to incomplete curing and excessively soft lenses. Furthermore, the cured lenses will have a low refractive index and be difficult to demold, resulting in mold damage. When the amount of monofunctional (meth)acrylate monomer used is too low (e.g., below 10 parts by weight), the viscosity of the thermosetting lens composition will be high, the refractive index of the obtained lenses will be high, and the Abbe number will be low. This not only affects the pouring efficiency of the thermosetting lens composition but also the performance of the obtained thermosetting lenses (such as refractive index, Abbe number, and demolding properties).

[0087] When the thermosetting lens composition of the present invention contains a polyfunctional (meth)acrylate monomer, the process time of the thermosetting reaction can be shortened. In this case, the amount of polyfunctional (meth)acrylate monomer used, based on a total of 100 parts by weight of the thermosetting lens composition, is preferably between about 1 part by weight and 15 parts by weight. In one embodiment of the present invention, when the amount of polyfunctional (meth)acrylate monomer used is excessive (e.g., above 15 parts by weight, especially above 20 parts by weight), the thermosetting lens composition will have problems such as high viscosity, which is not conducive to pouring to form a lens and easy generation of bubbles. Furthermore, the cured lens will become hard and brittle, with poor toughness, insufficient impact resistance, and a large shrinkage rate, which will easily lead to lens dimensional deformation.

[0088] Generally, thermosetting lenses with high refractive index have low Abbe numbers. The thermosetting lens composition of this invention uses 10 to 25 parts by weight of bisphenol A polyalkyl ether di(meth)acrylate monomer to adjust the refractive index, giving the thermosetting lens composition high refractive index characteristics. The cured lens has a refractive index of at least 1.48 and a high Abbe number. For example, a lens with a refractive index of 1.5 preferably has an Abbe number greater than 50 to meet industry requirements. Furthermore, to improve the impact resistance of the thermosetting lens, the aforementioned bisphenol A polyalkyl ether di(meth)acrylate monomer is preferably a di(meth)acrylate monomer modified with ethoxylated functional groups having multiple EO equivalents, wherein the EO equivalent number can be between 4 and 20, and preferably between 5 and 15.

[0089] To reduce the shrinkage of the composition after curing, the above-mentioned thermosetting lens composition needs to contain polyurethane acrylate monomers.

[0090] The thermosetting lens composition of this invention uses a safe and stable thermal initiator, and there are no particular limitations on the type of thermal initiator. Any thermal initiator that generates free radicals upon heating and initiates the polymerization reaction through free radical transport is a suitable thermal initiator.

[0091] In one embodiment of the present invention, when the amount of thermal initiator used is too large (e.g., more than 1 part by weight, especially more than 2 parts by weight), the thermosetting lens composition will have defects such as being too hard and brittle or lacking toughness after curing. When the amount of thermal initiator used is too small (e.g., less than 0.05 parts by weight, or even less than 0.03 parts by weight), the thermosetting lens composition will not cure completely.

[0092] The chain transfer agent in the thermosetting lens composition of this invention can be a known and commonly used chain transfer agent with specific functional groups, but diene-based chain transfer agents are not used. If diene-based chain transfer agents are used in the thermosetting lens composition of this invention, there is a problem of insufficient thermosetting crosslinking, resulting in poor physical properties of the formed lens.

[0093] Typical thermosetting lens compositions utilize the addition of fluorine to aid in demolding, the addition of styrene copolymers to adjust viscosity, and the addition of particles or microparticles to increase refractive index. It should be noted that the thermosetting lens composition of this invention does not contain solvents, fluorine, styrene monomers (e.g., styrene, methylstyrene, and divinylbenzene), styrene copolymers, or microparticles.

[0094] Preparation method

[0095] The method for preparing the thermosetting lens composition described herein involves curing the lens using a thermosetting process for approximately 20 to 24 hours, and includes the following steps:

[0096] S1. The thermosetting lens composition is mixed into an adhesive solution according to the proportions described in claim 2, and then vacuum defoamed to form a first mixture;

[0097] S2. The first mixture is injected into a light-transmitting mold to form a mold body, and the mold body is heated to form a second mixture;

[0098] S3. The second mixture is cured under controlled temperature to form a thermosetting lens;

[0099] S4. Demold and dry the thermosetting lens from S3, and then cure it a second time to obtain the thermosetting lens.

[0100] In another preferred embodiment, the vacuum defoaming described in S1 is carried out for 30 minutes at room temperature and a pressure of less than 0.1 torr.

[0101] In another preferred embodiment, a demolding step may be added after the second mixture is formed;

[0102] In another preferred embodiment, edge grinding, cleaning, and secondary curing steps can be optionally added after the above demolding step.

[0103] In another preferred embodiment, the machine used for demolding is a manual stamping machine.

[0104] In another preferred embodiment, the drying operation is carried out in an oven at 100°C for one hour.

[0105] The main advantages of this invention include:

[0106] (1) The method for manufacturing thermosetting lenses of the present invention and the thermosetting lenses obtained by the method are based on a thermosetting lens composition containing a specific proportion of various (meth)acrylate monomers and a thermal initiator, and a thermosetting step is performed. As a result, the obtained lenses not only have high process safety and high batch stability, but also achieve optimal reduction in deformation and shrinkage rate, and significantly improve the yield of post-processing of the lenses.

[0107] (2) The thermosetting lens of the present invention has advantages such as greater than 90% light transmittance, good shrinkage resistance and release properties (release marks and polymerization marks are not significant), better heat resistance and high Abbe number, and wide applicability of lens post-processing, thereby effectively improving various problems of known thermoplastic resin lenses or thermosetting resin lenses.

[0108] The present invention will be further illustrated below with reference to specific embodiments. It should be understood that these embodiments are for illustrative purposes only and are not intended to limit the scope of the invention. Experimental methods in the following embodiments, unless otherwise specified, are generally performed under conventional conditions or as recommended by the manufacturer. Percentages and parts are by weight unless otherwise stated. Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of skill in the art. Furthermore, any methods and materials similar to or equivalent to those described herein may be applied to the methods of the present invention. The preferred embodiments and materials described herein are for illustrative purposes only.

[0109] Example 1. Preparation of thermosetting lenses

[0110] Example 1 was prepared according to the reagent list in Tables 1 and 2. After the reagents were mixed evenly with their listed weight parts, the resulting adhesive was used to prepare a thermosetting lens according to the following steps:

[0111] (1) The thermosetting lens composition is placed in a vacuum oven at room temperature and the internal pressure is less than 0.1 torr for vacuum defoaming for 30 minutes to form a first mixture.

[0112] (2) The first mixture is injected into a light-transmitting mold to form a mold body, and the mold body is heated to form a second mixture. The heating procedure used is as follows:

[0113] First, heat the mold from room temperature to 41°C and hold it at 41°C for 11 hours; then heat the mold from 41°C to 110°C and hold it at 110°C for 8 hours; finally, cool the mold from 110°C to 55°C and hold it there for 1 hour.

[0114] (3) The second mixture is cured under temperature control to form a thermosetting lens.

[0115] (4) After the cured lens is demolded using a manual punch, it is placed in a 100°C oven for one hour to perform a secondary curing process.

[0116] (5) After that, the lens is removed from the mold and after edge grinding and cleaning, the following lens evaluation items are carried out, and the results are shown in Table 3.

[0117] Examples 2 to 5: Preparation of thermosetting lenses

[0118] Examples 2 to 5 were prepared by mixing the reagents and dosages listed in Table 1 in the same manner as in Example 1, casting the adhesive into molds, curing them, and then demolding them. The following lens evaluation items were then performed, and the results are shown in Table 3.

[0119] Comparative Examples 1 to 4

[0120] Comparative Examples 1 to 4 were prepared by mixing the reagents and dosages listed in Table 1 in the same manner as in Example 1, testing the performance of the adhesive, and then molding the mixture to form a mold body. The following lens evaluation items were then performed, and the results are shown in Table 3.

[0121] Evaluation method: Performance testing of thermosetting lenses

[0122] The thermosetting lenses of Examples 1 to 5 and Comparative Examples 1 to 4 were subjected to the following performance tests, and the results are shown in Table 3.

[0123] Transmittance: Evaluated using visual inspection and a UV-Vis luminance meter. Visual inspection involves observing the front, oblique, and side edges of the lens, primarily focusing on the absence of white fog or reflection. The UV-Vis luminance meter is used to test the shaped lens. A transmittance greater than 92% is required.

[0124] ○: No white fog or white reflection, or transmittance >92%

[0125] ╳: White fog or reflection, or penetration rate <92%.

[0126] Demolding capability: After curing, a demolding step is required to release the manufactured lens from the glass mold. Demolding must not damage the mold or the cured material. The demolding capability of the lenses in Examples 1 to 5 and Comparative Examples 1 to 4 was evaluated visually, and the judgment criteria are as follows:

[0127] ○: Can be completely demolded

[0128] ╳: Incomplete demolding

[0129] Yellowing: After removing the cured lens, a high-temperature test was conducted under condition a (temperature 100℃, time 1 hour). The colorimetry before and after the high-temperature test was measured using a transmission colorimeter (NE4000; NIPPON DENSHOKU) to obtain the color difference value (Δb) (i.e., the b-value after the high-temperature test minus the b-value before the high-temperature test). Δb < 3.0 was defined as no significant yellowing, and the judgment criteria are as follows:

[0130] ○: No obvious yellowing

[0131] ╳: Noticeable yellowing

[0132] Heat resistance (90℃): The cured lens is placed in a 90℃ oven and tested by hand after 30 minutes. The evaluation standard is that the lens does not produce obvious deformation.

[0133] ○: No obvious deformation

[0134] ╳: Significant deformation

[0135] Release marks: Before the demolding step after curing, visually inspect the lens for signs of detachment from the glass mold. Premature demolding will result in release marks.

[0136] ○: No mold release lines

[0137] ╳: There are mold release lines

[0138] Polymerization pattern: The cured lens is tested using a polarizing filter to ensure that it does not produce halos or white reflections.

[0139] ○: No halo or white reflection

[0140] ╳: There is a halo or white reflection.

[0141] Refractive index: The refractive index of the adhesive in the thermosetting lens components was measured at 25°C using a commercially available refractometer (e.g., ATAGO DR-A1 refractometer).

[0142] Abbe number: The Abbe number of the adhesive in the composition of thermosetting lenses is measured at 20°C using a commercially available refractometer (e.g., ATAGO DR-A1 refractometer).

[0143] Viscosity value: The viscosity of the photocurable resin composition was measured at 25°C using a commercially available viscometer (Brookfield, LVT).

[0144] EO equivalent number of the composition: Calculated using the amounts of each component listed in Table 1, the resulting value is defined as the EO equivalent number. The calculation formula is as follows:

[0145] [Amount of each component used (parts by weight) × EO equivalent of each component in the reagent list] / Total weight of the composition (Formula I).

[0146] Table 1. Proportions of Raw Materials and Reagents for Thermosetting Lenses

[0147]

[0148] Table 2. Reagent List

[0149]

[0150] Table 3. Evaluation of Examples 1 to 5 and Comparative Examples 1 to 4

[0151]

[0152] As can be seen from the evaluation results in Table 3, the thermosetting lenses prepared in Examples 1 to 5 have a light transmittance greater than 92% and better release properties than those in Comparative Examples 1 to 4. Therefore, they can be applied to safety lenses, optical components, etc.

[0153] As shown in Table 3, the EO equivalent numbers of Example 3 and Comparative Example 1 are similar. However, compared to Example 3 which uses the bisphenol A oxyacetylene oxide component, the lens obtained in Comparative Example 1 has poor heat resistance and release properties. Further comparing Example 3 and Comparative Example 2, even though Comparative Example 2 has a higher EO equivalent number (3.5), the lens obtained in Comparative Example 2, lacking the use of the bisphenol A oxyacetylene oxide component, still suffers from poor heat resistance and release properties.

[0154] Furthermore, comparing Example 4 with Comparative Examples 3 to 4, it can be seen that although all three used bisphenol A oxyacetylene oxide component, the EO equivalent number of Comparative Examples 3 to 4 was insufficient. In particular, the amount of bisphenol A oxyacetylene oxide component used in Comparative Example 4 was also insufficient (based on the total amount of thermosetting lens composition used being 100 parts by weight, the amount of bisphenol A oxyacetylene oxide component used was less than 10 parts by weight), which resulted in poor lens molding conditions and defects such as release lines and polymerization lines during the lens manufacturing process.

[0155] As can be seen from Examples 1 to 5, when bisphenol A dimethacrylate (BPA) is selected as a component (monomers b to d) in the lens composition and the amount is greater than 10 parts by weight (based on a total amount of 100 parts by weight for thermosetting lens compositions), the resulting lens has excellent performance. Furthermore, the EO equivalent number (2.3-3.4) can be adjusted by using different proportions of monomers, and the Abbe number of the lens (49.3-58.9) can be adjusted accordingly.

[0156] As can be seen from the above embodiments of the present invention, the method for manufacturing thermosetting lenses of the present invention and the resulting thermosetting lenses utilize a thermosetting lens composition containing a specific proportion of various (meth)acrylate monomers and a thermal initiator to perform a thermosetting step. The resulting thermosetting lenses exhibit better heat resistance and better optical properties (Abbe number), thereby effectively improving various problems of conventional thermosetting resin lenses.

[0157] All documents mentioned in this invention are incorporated herein by reference as if each document were individually incorporated by reference. Furthermore, it should be understood that after reading the foregoing teachings of this invention, those skilled in the art can make various alterations or modifications to this invention, and these equivalent forms also fall within the scope defined by the appended claims.

Claims

1. A thermosetting lens, characterized in that, The thermosetting lens is made from a thermosetting lens composition, wherein the thermosetting lens composition comprises: Component a) at least one of a monofunctional (meth)acrylate monomer and a polyfunctional (meth)acrylate monomer; Component b) at least two di(meth)acrylate monomers having alkyl ether groups; Component c) Polyurethane acrylate monomer; Component d) chain transfer agent, wherein the chain transfer agent does not contain diene chain transfer agents; and Component e) Thermal initiator, At least one of the components b) is selected from bisphenol A polyalkyl ether di(meth)acrylate monomers; Wherein, based on a total usage of 100 parts by weight of the thermosetting lens composition, the usage of the bisphenol A polyalkyl ether di(meth)acrylate monomer is 10-25 parts by weight, and the usage of component c) is 3-80 parts by weight. The alkyl ether (EO) equivalent number of the thermosetting lens composition is between 2.3 and 3.

4. The Abbe number of the thermosetting lens is greater than 49.

2. The thermosetting lens as described in claim 1, characterized in that, Based on a total usage of 100 parts by weight of the thermosetting lens composition, the proportions of each component are as follows: The amount of monofunctional (meth)acrylate monomer used in component a) is 5-60 parts by weight; The amount of the polyfunctional (meth)acrylate monomer used in component a) is 0-30 parts by weight; The amount of the di(meth)acrylate monomer having an alkyl ether group used in component b) is 10-90 parts by weight. The amount of component d) used is 0.05-10 parts by weight; The amount of component e) used is 0.05-5 parts by weight.

3. The thermosetting lens as described in claim 1, characterized in that, The amount of the monofunctional (meth)acrylate monomer used is 15-35 parts by weight.

4. The thermosetting lens as described in claim 1, characterized in that, The thermosetting lens has a refractive index between 1.48 and 1.

52.

5. The thermosetting lens as described in claim 1, characterized in that, The thermosetting lens composition has one or more features selected from the group consisting of: 1) For component b), in addition to containing the bisphenol A polyalkyl ether di(meth)acrylate monomer, it also contains a substance selected from the group consisting of: 3-hydroxy-2,2-dimethylpropionic acid 3-hydroxy-2,2-dimethylpropyl diacrylate, 1,6-hexanediol diacrylate, ethoxylated 1,6-hexanediol diacrylate, dipropylene glycol diacrylate, tricyclodecanediethanol diacrylate, ethoxylated dipropylene glycol diacrylate, neopentyl glycol diacrylate, propionyl neopentyl glycol diacrylate, ethoxylated bisphenol A. Dimethacrylate, 2-methyl-1,3-propanediol diacrylate, ethoxylated-2-methyl-1,3-propanediol diacrylate, 2-butyl-2-ethyl-1,3-propanediol diacrylate, ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, tripropylene glycol dimethacrylate, 1,4-butanediol dimethacrylate, 1,6-hexanediol dimethacrylate, allylated cyclohexyl dimethacrylate, polyethylene glycol diacrylates with an EO number of 1 to 20, or combinations thereof; 2) The monofunctional (meth)acrylate monomer in component a) is selected from the group consisting of: methyl methacrylate, butyl methacrylate, 2-phenoxyethyl acrylate, ethoxylated 2-phenoxyethyl acrylate, 2-(2-ethoxyethoxy)ethyl acrylate, cyclotrimethylolpropane methyl acetal acrylate, β-carboxyethyl acrylate, 3,3,5-trimethylcyclohexyl acrylate, o-phenylphenoxyethyl acrylate, 2-(p-isopropylphenyl-phenoxy)-ethyl acrylate, methyl laurate, isooctyl acrylate, methyl stearate, isodecyl acrylate, isobornyl methacrylate, benzyl acrylate, 2-hydroxyethyl methacrylate phosphate, caprolactone acrylate, hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, or combinations thereof; 3) The polyfunctional (meth)acrylate monomer in component a) has three or more functional groups, and the polyfunctional (meth)acrylate monomer is selected from the group consisting of: tris(2-hydroxyethyl)isocyanurate triacrylate, pentaerythritol triacrylate, ethoxylated trimethylolpropane triacrylate, propoxylated trimethylolpropane triacrylate, trimethylolpropane trimethacrylate, pentaerythritol tetraacrylate, ethoxylated pentaerythritol tetraacrylate, bis-trimethylolpropane tetraacrylate, propoxylated pentaerythritol tetraacrylate, dipentaerythritol hexaacrylate, ethoxylated trimethylolpropane trimethacrylate, propoxylated glycerol trimethacrylate, propoxylated glycerol triacrylate, tri(propyleneoxyethyl)isocyanurate, trimethylolpropane triacrylate, or combinations thereof; 4) For component b), the bisphenol A polyalkyl ether di(meth)acrylate monomer is selected from the group consisting of: bisphenol A dimethacrylate, ethoxylated bisphenol A diacrylate, and ethoxylated bisphenol A dimethacrylate; 5) Component c) is selected from the following group: diacrylate isocyanurate, dimethacrylate isocyanurate, triacrylate isocyanurate and polyurethane diacrylate and combinations thereof; 6) Component e) is selected from the group consisting of: benzene peroxide, cumene hydroperoxide, dicumene peroxide, tert-butyl hydroperoxide, tert-butyl maleic acid peroxide, diacetyl peroxide, lauroyl peroxide, a mixture of one or more of the above peroxides with an amino acid or sulfonic acid, a mixture of one or more of the above peroxides with a cobalt-containing compound, azobisisobutyronitrile, azobisisoheptanenitrile, and combinations thereof.

6. The thermosetting lens as described in claim 1, characterized in that, The thermosetting lens composition further comprises additives selected from the group consisting of dyes, antioxidants, heat stabilizers, dispersants, release agents, wetting agents, defoamers, anti-yellowing agents, ultraviolet absorbers, or combinations thereof.

7. A method for manufacturing a thermosetting lens, characterized in that, The lens is manufactured using the thermosetting lens composition as described in any one of claims 1 to 6, specifically comprising the following steps: S1. The thermosetting lens composition is mixed into an adhesive solution according to the proportions described in claim 2, and then vacuum defoamed to form a first mixture; S2. The first mixture is injected into a light-transmitting mold to form a mold body, and the mold body is heated to form a second mixture; S3. The second mixture is cured under controlled temperature to form a thermosetting lens; S4. Demold and dry the thermosetting lens from S3, and then cure it a second time to obtain the thermosetting lens.

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