Blue light blocking contact lenses and methods of making the same

Abstract

Two types of contact lenses that block blue light are provided, which are formed by curing different compositions. The first composition includes a blue light blocking component formed by mixing or reacting a first hydrophilic monomer with a yellow dye, a first colored dye component formed by mixing or reacting a second hydrophilic monomer with a first colored dye, at least one third hydrophilic monomer, a crosslinker, and a initiator. The first colored dye includes a green dye, a cyan dye, a blue dye, an orange dye, a red dye, a black dye, or a combination thereof. The second composition includes a blue light blocking component, at least one hydrophilic monomer, a crosslinker, and a initiator. The blue light blocking component is formed by mixing or reacting glycerol monomethacrylate with a yellow dye. Further, a method of making the above contact lenses is provided. Due to the improved solubility and compatibility of the dyes in the compositions, the above contact lenses can have good blue light blocking effect and color rendering.

Description

TECHNICAL FIELD

[0001] The present disclosure relates to ophthalmic products and methods of making the same, in particular, to blue light blocking contact lenses and methods of making the same. BACKGROUND

[0002] In recent years, due to the booming development of 3C products, many smart devices, such as mobile phone screens, tablet displays, computer screens, light-emitting diode lamps (LED lamps), etc., have been widely used in people's lives. However, the background light source of these smart devices contains blue light, and when the human eye directly looks at the blue light for a long time, it will cause damage to the retina.

[0003] Because the wavelength of blue light between 380 nm and 500 nm is shorter, it has a larger energy, and it is more likely to cause eye damage than light with other wavelengths, especially damaging the retina. The retina needs to undergo photochemical reactions to produce vision at any time, and the reaction process consumes oxygen. Under the stimulation of blue light, many free radicals are easily produced to damage cells. Moreover, the cell membrane of the photoreceptor cells of the retina contains many fatty acids, which are also easily produced under the stimulation of blue light, causing the retina cells to be damaged or die.

[0004] Most of the anti-blue light lenses on the market are yellow, although they have anti-blue light function, but the aesthetic appearance is not good. Consumers wearing anti-blue light lenses have a yellow jaundice disease in the eye wheel (corneal limbus), which reduces the willingness of consumers to wear. In view of this, there is an urgent need to develop anti-blue light lenses that can block blue light and have aesthetic appearance to improve their commercial value. SUMMARY

[0005] The present disclosure provides a blue light blocking contact lens formed by curing a composition. The composition includes: a blue light blocking component formed by mixing or reacting a first hydrophilic monomer and a yellow dye, a first colored dye component formed by mixing or reacting a second hydrophilic monomer and a first colored dye, at least one third hydrophilic monomer, a crosslinking agent, and a initiator. The first colored dye includes a green dye, a cyan dye, a blue dye, an orange dye, a red dye, a black dye, or a combination thereof.

[0006] In some embodiments, the first, second, and third hydrophilic monomers are independently selected from the group consisting of N-vinylpyrrolidone (NVP), 2-hydroxyethyl methacrylate (HEMA), glycidyl methacrylate (GMA), glycerol monomethacrylate (GMMA), methacrylic acid, acrylic acid, N,N-dimethylacrylamide (DMA), N,N-diethyl acrylamide, N-vinyl-N-methyl acetamide, 2-methacryloyloxyethyl phosphorylcholine, and 2-hydroxybutylmethacrylate.

[0007] In some embodiments, the composition further comprises a second colored dye component, the second colored dye component being formed by mixing or reacting a fourth hydrophilic monomer and a second colored dye, wherein the second colored dye comprises a green dye, a cyan dye, a blue dye, an orange dye, a red dye, a black dye, or a combination thereof.

[0008] In some embodiments, the fourth hydrophilic monomer is selected from the group consisting of N-vinylpyrrolidone, 2-hydroxyethyl methacrylate, glycidyl methacrylate, glycerol monomethacrylate, methacrylic acid, acrylic acid, N,N-dimethylacrylamide, N,N-diethyl acrylamide, N-vinyl-N-methyl acetamide, 2-methacryloyloxyethyl phosphorylcholine, and 2-hydroxybutylmethacrylate.

[0009] In some embodiments, the yellow dye is 0.01 wt% to 2 wt% and the first colored dye is 0.01 wt% to 2 wt%, based on 100 wt% of the composition.

[0010] In some embodiments, the yellow dye is 0.01 wt% to 2 wt% and the first colored dye is 0.01 wt% to 2 wt%, based on 100 wt% of the composition.

[0011] In some embodiments, the weight ratio of the yellow dye to the first hydrophilic monomer is 1:0.1 to 1:10.

[0012] In some embodiments, the weight ratio of the first colored dye to the second hydrophilic monomer is from 1 :0.1 to 1 :10.

[0013] In some embodiments, the yellow dye is selected from the group consisting of Reactive Yellow 15, Reactive Yellow 86, and Pigment Yellow 83.

[0014] In some embodiments, the first colored dye has an ethylenically-base polymerizable group, a sulfonic group, a sulfonyl group, a sulfonate group, an amide group, or a combination thereof.

[0015] In some embodiments, the first colored dye is selected from the group consisting of Reactive Blue 4, Reactive Blue 19, Reactive Blue 21, Reactive Blue 69, Reactive Blue 163, Reactive Blue 246, Reactive Blue 247, Reactive Red 11, Reactive Red 180, Reactive Black 5, Reactive Orange 78, and Pigment Green 7.

[0016] The present disclosure provides a method of making the blue light blocking contact lens of any of the preceding embodiments, comprising the following operations. Mixing a first hydrophilic monomer and a yellow dye to form a first mixture. Heating the first mixture to 25°C to 80°C for 0.5 hours to 24 hours to form a blue light blocking component. Mixing a second hydrophilic monomer and a first colored dye to form a second mixture. Heating the second mixture to 25°C to 80°C for 0.5 hours to 24 hours to form a first colored dye component. Curing the blue light blocking component, the first colored dye component, at least one third hydrophilic monomer, a crosslinking agent, and a starter.

[0017] In some embodiments, the method further comprises adding a basic substance and an inhibitor to the first mixture before heating the first mixture to 25°C to 80°C.

[0018] In some embodiments, the method further comprises adding a basic substance and an inhibitor to the second mixture before heating the second mixture to 25°C to 80°C.

[0019] The present disclosure provides a blue light blocking contact lens formed from a cured composition. The composition comprises a blue light blocking component, at least one hydrophilic monomer, a crosslinker, and a starter. The blue light blocking component is formed from a mixture or reaction of glycerol monomethacrylate (GMMA) and a yellow dye.

[0020] In some embodiments, the yellow dye is 0.01 wt% to 2 wt% based on 100 wt% of the composition.

[0021] In some embodiments, the yellow dye is selected from the group consisting of Reactive Yellow 15, Reactive Yellow 86, and Pigment Yellow 83.

[0022] In some embodiments, the weight ratio of the yellow dye to the glycerol monomethacrylate is 1:0.1 to 1:10.

[0023] The present disclosure provides a method of preparing the blue light blocking contact lens of any of the preceding embodiments, comprising the following operations. Mixing glycerol monomethacrylate and a yellow dye to form a mixture. Heating the mixture to 25°C to 80°C for 0.5 hours to 24 hours to form a blue light blocking component. Curing the blue light blocking component, at least one hydrophilic monomer, a crosslinker, and a starter.

[0024] In some embodiments, the method further comprises adding a basic substance and an inhibitor to the mixture before heating the mixture to 25°C to 80°C.

[0025] BRIEF DESCRIPTION OF DRAWINGS

[0026] The present disclosure can be more fully understood with reference to the following detailed description of embodiments when read in conjunction with the accompanying drawings, in which:

[0027] Figure 1 is a contact lens obtained according to the preparation method of various embodiments of the present disclosure.

[0028] Figures 2 to 7is a transmittance spectrum of a contact lens according to various embodiments of the present disclosure.

[0029] [Explanation of main element symbols]

[0030] B1: Blue lens

[0031] B2: Gray-blue lens

[0032] G: Gray lens

[0033] G1: Yellow-green lens

[0034] G2: Green lens

[0035] G3: Bright green lens

[0036] O1: Orange-red lens

[0037] O2: Orange lens

[0038] O3: Orange-yellow lens

[0039] P1: Indigo lens

[0040] P2: Purple lens

[0041] R1: Dark red lens

[0042] R2: Brown-red lens

[0043] Y1: Amber lens

[0044] Y2: Dark yellow lens

[0045] Y3: Yellow lens

[0046] BLANK, b1, b2, g, g1, g2, g3, o1, o2, o3, p1, p2, r1, r2, y1, y2, y3: Curve

[0047] BEST MODE FOR CARRYING OUT THE INVENTION

[0048] The embodiments of the present disclosure related to "contact lenses blocking blue light" are explained below by specific concrete examples, and those skilled in the art can understand the advantages and effects of the present disclosure from the disclosed content. The present disclosure can be implemented or applied by other different concrete examples, and various modifications and changes can be made to the details based on different views and applications without departing from the concept of the present disclosure. The following embodiments will further explain the related technical content of the present disclosure in detail, but the disclosed content is not intended to limit the protection scope of the present disclosure.

[0049] Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure belongs. If the terms are defined in plural, the singular form of the terms is also encompassed.

[0050] All percentages mentioned herein are percentages by weight, unless otherwise indicated. When a range of values is provided, all combinations and subcombinations of ranges are encompassed, unless otherwise indicated. In this document, references to a range of values, for example, "from x to y," are shorthand for "x or more and y or less," unless otherwise indicated. Thus, a numerical range "from x to y" is intended to

[0051] Although the methods disclosed herein are described below with regard to a series of operations or steps, the order in which the operations or steps are presented is not to be construed as a limitation of the disclosure. For example, certain operations or steps can be performed in different orders and / or concurrently with other steps. Furthermore, not all illustrated operations, steps, and / or features can be required to implement an embodiment of the disclosure. Additionally, each operation or step recited herein can include multiple sub-steps or actions.

[0052] Research results on blue light show that high-energy blue light from 460 nm to 500 nm helps memory and cognitive function, and makes people feel happy, so this blue light is beneficial blue light. Blue light from 380 nm to 460 nm is easy to cause eye damage, so it is harmful blue light. The present disclosure provides contact lenses that block blue light, which have good anti-blue light properties. In some embodiments, the contact lenses of the present disclosure have a blocking rate of 5% to 30% for harmful blue light with a wavelength of 380 nm to 460 nm. Furthermore, the contact lenses of the present disclosure are colored contact lenses, such as red, orange, yellow, green, blue, or gray, which have anti-blue light properties and good aesthetics. The present disclosure also provides a method for preparing contact lenses that block blue light. Before curing the composition for preparing the contact lenses, the dye is pretreated with a hydrophilic monomer, that is, the two are mixed or allowed to react, to improve the solubility of the dye in the composition for forming the contact lenses, thereby improving the color development and blue light blocking rate of the contact lenses. In other words, the pretreated dye added to the composition can effectively improve the formulation compatibility, the degree of color brightness, the uniformity of the color of the lenses, and the blocking rate of the lenses to blue light, thereby obtaining contact lenses with a variety of colors. Furthermore, the contact lenses of the present disclosure can be hydrogel contact lenses or silicone hydrogel contact lenses. Various embodiments of the present disclosure will be described below.

[0053] The present disclosure provides a blue light blocking contact lens formed from a cured composition. The composition includes a blue light blocking component formed from a first hydrophilic monomer mixed with or reacted with a yellow dye, a first colored dye component formed from a second hydrophilic monomer mixed with or reacted with a first colored dye, at least one third hydrophilic monomer, a crosslinker, and a starter. The blue light blocking component is formed by pre-treating the yellow dye with the first hydrophilic monomer. On the other hand, the first colored dye component is formed by pre-treating the first colored dye with the second hydrophilic monomer, wherein the first colored dye includes a green dye, a cyan dye, a blue dye, an orange dye, a red dye, a black dye, or a combination thereof. Because both the yellow dye and the first colored dye are pre-treated, the solubility of both in the composition and the compatibility of both with other components can be greatly improved, resulting in a contact lens with good color development and blue light blocking rate. In some embodiments, the composition includes one or more blue light blocking components, and the plurality of blue light blocking components includes different pre-treated yellow dyes.

[0054] The composition for making a contact lens can include one or more different colored dye components, such as two, three, or four. In some embodiments, the composition includes a first and a second colored dye component, and the second colored dye component is formed from a fourth hydrophilic monomer mixed with or reacted with a second colored dye, wherein the second colored dye includes a green dye, a cyan dye, a blue dye, an orange dye, a red dye, a black dye, or a combination thereof. The colors of the first and second colored dye components can be the same or different. Different colored contact lenses can be formulated by mixing different colored dye components. For example, a composition including a blue light blocking component (containing a pre-treated yellow dye) and two colored dye components (containing pre-treated blue and red dyes) can be used to form a purple contact lens. In other embodiments, the composition further includes a third colored dye component, which can have the same or different color as the first and / or second colored dye components. Embodiments of the third colored dye component can be similar to those of the second colored dye component, which will not be repeated here.

[0055] In some embodiments, the first, second, third, and fourth hydrophilic monomers are independently selected from the group consisting of N-vinylpyrrolidone, 2-hydroxyethyl methacrylate, glycidyl methacrylate, glycerol monomethacrylate, methacrylic acid, acrylic acid, N,N-dimethylacrylamide, N,N-diethylacrylamide, N-vinyl-N-methylacetamide, 2-methacryloyloxyethyl phosphorylcholine, and 2-hydroxybutyl methacrylate.

[0056] In some embodiments, the yellow dye is 0.01 to 2 wt% and the first colored dye is 0.01 to 2 wt% based on 100 wt% of the composition. The yellow dye is, for example, 0.01, 0.05, 0.1, 0.5, 1, 1.5, or 2 wt%. The first colored dye is, for example, 0.01, 0.05, 0.1, 0.5, 1, 1.5, or 2 wt%. In some embodiments, the yellow dye is 0.01 to 2 wt% and the total of the first colored dye and the second colored dye is 0.01 to 2 wt% based on 100 wt% of the composition. The total is, for example, 0.01, 0.05, 0.1, 0.5, 1, 1.5, or 2 wt%. When the weight percentage falls within the above ranges, the contact lenses have good color development and good blue light blocking, and the wearer can still maintain good visual perception.

[0057] In some embodiments, the yellow dye is 0.01 to 2 parts by weight and the first colored dye is greater than 0 parts by weight and less than or equal to 2 parts by weight. The yellow dye is, for example, 0.01, 0.05, 0.1, 0.5, 1, 1.5, or 2 parts by weight. The first colored dye is, for example, 0.01, 0.05, 0.1, 0.5, 1, 1.5, or 2 parts by weight. When the parts by weight fall within the above ranges, the contact lenses have good color development and good blue light blocking, and the wearer can still maintain good visual perception. In some embodiments, the first hydrophilic monomer, the second hydrophilic monomer, and the third hydrophilic monomer are 30 to 99 parts by weight. In other embodiments, the first hydrophilic monomer, the second hydrophilic monomer, the third hydrophilic monomer, and the fourth hydrophilic monomer are 30 to 99 parts by weight.

[0058] In some embodiments, the weight ratio of the yellow dye to the first hydrophilic monomer is 1:0.1 to 1:10, which range enables the best compatibility between the two. The weight ratio is, for example, 1:0.1, 1:0.5, 1:1, 1:2, 1:5, or 1:10. In some embodiments, the weight ratio of the first colored dye to the second hydrophilic monomer is 1:0.1 to 1:10, which range enables the best compatibility between the two. The weight ratio is, for example, 1:0.1, 1:0.5, 1:1, 1:2, 1:5, or 1:10. In some embodiments, the weight ratio of the second colored dye to the fourth hydrophilic monomer is 1:0.1 to 1:10, which range enables the best compatibility between the two. The weight ratio is, for example, 1:0.1, 1:0.5, 1:1, 1:2, 1:5, or 1:10. When the parts by weight fall within the above ranges, the yellow dye, the first colored dye, and the second colored dye have good solubility and good compatibility in the composition, thereby enabling the contact lenses to have good color development.

[0059] In some embodiments, the yellow dye is selected from the group consisting of Reactive Yellow 15, Reactive Yellow 86, and Pigment Yellow 83.

[0060] In some embodiments, the first colored dye and the second colored dye independently have a vinyl polymerizable group, a sulfonic acid group, a sulfonyl group, a sulfonate group, an amide group, or a combination thereof. For example, the first colored dye and the second colored dye are independently selected from the group consisting of Reactive Blue 4, Reactive Blue 19, Reactive Blue 21, Reactive Blue 69, Reactive Blue 163, Reactive Blue 246, Reactive Blue 247, Reactive Red 11, Reactive Red 180, Reactive Black, Reactive Orange 78, and Pigment Green.

[0061] In some embodiments, the crosslinking agent is selected from the group consisting of ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, allyl methacrylate, ethylene glycol diallyl ether, triethylene glycol diallyl ether, tetraethylene glycol diallyl ether, 1,3,5-triallyl-l,3,5-triazine-2,4,6(lH,3H,5H)-trione, and 1,1,1-trimethylolpropane trimethacrylate.

[0062] In some embodiments, the initiator is selected from the group consisting of a phosphine-oxide-based initiator and a titanium metallocene-based initiator. For example, the phosphine-oxide-based initiator is selected from the group consisting of phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide, bis(2,4,6-trimethylbenzoyl)phenyl phosphine oxide, and bis(2,6-dimethoxylbenzoyl)(2,4,4-trimethylpentyl)phosphine oxide. For example, the titanium metallocene-based initiator includes dicyclopentadienyl bis[2,4-difluoro-3-(1-pyrrolyl)phenyl]titanium.

[0063] In some embodiments, the composition for making blue light blocking contact lenses further includes a UV blocking monomer. For example, the UV blocking monomer is selected from the group consisting of a monomer having benzophenone and a monomer having benzotriazole. The monomer having benzophenone includes, for example, 4-methacryloxy-2-hydroxy benzophenone, 4-(2-acryloxyethoxy-2-hydroxy benzophenone), or a combination thereof.

[0064] The present disclosure provides a method of making the blue light blocking contact lens of any of the preceding embodiments, comprising the following operations. Mixing a first hydrophilic monomer and a yellow dye to form a first mixture. Heating the first mixture to a temperature of 25°C to 80°C for a time period of 0.5 hours to 24 hours to form a blue light blocking component. Mixing a second hydrophilic monomer and a first colored dye to form a second mixture. Heating the second mixture to a temperature of 25°C to 80°C for a time period of 0.5 hours to 24 hours to form a first colored dye component. If the heating temperature is higher than 80°C, too many byproducts can be generated, which can reduce the dye bonding rate and the blue light blocking rate of the lens. Curing a composition containing the blue light blocking component, the first colored dye component, at least one third hydrophilic monomer, a crosslinking agent, and a initiator to form a contact lens. In some embodiments, the temperature of heating the first mixture or the second mixture is 25, 35, 45, 55, 65, 75, or 80°C. In some embodiments, the time period of heating the first mixture or the second mixture is 0.5, 1, 5, 10, 15, 20, or 24 hours. In some embodiments, the contact lens is a hydrogel contact lens or a silicone hydrogel contact lens. In some embodiments, the composition further comprises a silicone-containing monomer. In some embodiments, the curing operation is performed by injecting the composition into a gap between a male mold and a female mold, polymerizing the composition by UV light, and curing to form a solid lens. The solid lens is then hydrated, placed in a contact lens packaging solution, sealed, and subjected to a high-temperature sterilization process to obtain the blue light blocking contact lens.

[0065] In some embodiments, the method further comprises adding a base and an inhibitor to the first mixture before heating the first mixture, so that the heating operation is performed on the first mixture containing the first hydrophilic monomer, the yellow dye, the base, and the inhibitor. Thus, after heating, the first hydrophilic monomer and the yellow dye are bonded together to form the blue light blocking component. According to the above operation, the yellow dye is pretreated by “synthesis method” to improve the solubility of the blue light blocking component in the composition, thereby improving the color development and blue light blocking rate of the contact lens. In some embodiments, the pH value of the first mixture is 10-14. For example, the pH value is 10, 11, 12, 13, or 14. In some embodiments, the inhibitor comprises Mequinol (MeHQ). In some embodiments, the base comprises NaOH. In some embodiments, the first mixture does not contain water. Under the same experimental conditions of dye addition amount, the reaction performed in a water-free environment can result in a higher blue light blocking rate of the lens, while the reaction performed in a water-containing environment can result in a lower blue light blocking rate of the lens.

[0066] The following is a reaction scheme for pre-treating Reactive Yellow 15 with a hydrophilic monomer, glyceryl monomethacrylate (GMMA), to form a blue light blocking component in a basic environment. First, Reactive Yellow 15 in the presence of sodium hydroxide (NaOH) and an inhibitor (MeHQ) forms Reactive Yellow 15 with a vinyl group, which then reacts with GMMA to form a blue light blocking component. Compared to untreated Reactive Yellow 15, GMMA pre-treated Reactive Yellow 15 has better solubility and compatibility in the composition of contact lenses, thereby improving its color development and blue light blocking rate. The following reaction scheme can be applied to dyes with ethylenically-base polymerizable groups, sulfonic groups, sulfonyl groups, sulfonate groups, amide groups, or combinations thereof.

[0067]

[0068] In some embodiments, the first mixture does not add a basic substance and an inhibitor, such as sodium hydroxide and MeHQ, so that the first hydrophilic monomer and the yellow dye do not form a bond in the mixture after heating. This mixture is a blue light blocking component. According to the above operation, the yellow dye is pre-treated by the "mixing method" to improve the solubility of the subsequent blue light blocking component in the composition, thereby improving the color development of the contact lenses. It is worth noting that if the untreated yellow dye, hydrophilic monomer, crosslinking agent and initiator are directly mixed when preparing the composition of contact lenses, the yellow dye will have insufficient compatibility, which will cause insufficient color development of the contact lenses and poor blue light resistance. In some embodiments, the first mixture does not contain water.

[0069] In some embodiments, the method further comprises adding a basic substance and an inhibitor to the second mixture before heating the second mixture to a temperature of 25°C to 80°C, so that the heating is performed on the second mixture containing the second hydrophilic monomer, the first colored dye, the basic substance, and the inhibitor. Thus, after heating, the second hydrophilic monomer and the first colored dye are bonded together to form the first colored dye component. According to the above operation, the first colored dye is pretreated by "synthesis method" to improve the solubility of the first colored dye component in the composition, thereby improving the color development of the contact lens. In some embodiments, the pH value of the second mixture is 10 to 14. The pH value is, for example, 10, 11, 12, 13, or 14. In some embodiments, the inhibitor includes hydroquinone monomethyl ether. In some embodiments, the basic substance includes sodium hydroxide. In some embodiments, the second mixture does not contain water. Under the same experimental conditions of the amount of dye added, the reaction is performed in a water-free environment, which can result in a higher blue light blocking rate of the lens; on the other hand, the reaction is performed in a water-containing environment, which results in a lower blue light blocking rate of the lens.

[0070] In some embodiments, the second mixture does not contain a basic substance and an inhibitor, such as sodium hydroxide and MeHQ, so that in the mixture after heating, the second hydrophilic monomer and the first colored dye do not form a bond, and the mixture is the first colored dye component. According to the above operation, the first colored dye is pretreated by "mixing method" to improve the solubility of the subsequent first colored dye component in the composition, thereby improving the color development of the contact lens. It is worth noting that if the untreated first colored dye, hydrophilic monomer, crosslinking agent, and initiator are directly mixed when the contact lens composition is prepared, the first colored dye will have the problem of insufficient compatibility, which will cause insufficient color development of the contact lens. In some embodiments, the second mixture does not contain water.

[0071] In some embodiments, the method further comprises mixing a fourth hydrophilic monomer and a second colored dye to form a third mixture, heating the third mixture to a temperature of 25°C to 80°C for a time period of 0.5 hours to 24 hours to form a second colored dye component. The second colored dye component is added to the composition, and the curing operation is performed. If the above heating temperature is higher than 80°C, too many by-products can be generated, thereby reducing the dye bonding rate and reducing the blue light blocking rate of the lens. In some embodiments, the method further comprises adding a basic substance and an inhibitor to the third mixture before heating the third mixture to a temperature of 25°C to 80°C. In some embodiments, the third mixture does not contain a basic substance and an inhibitor. The embodiments of the third mixture can refer to the embodiments of the second mixture, which will not be described again.

[0072] In some embodiments, the silicon-containing monomer comprises 3-[tris(trimethylsiloxy)silyl]propyl methacrylate (TRIS), (3-methacryloxy-2-hydroxypropoxy)propylbis(trimethylsiloxy)methylsilane (SiGMA), 3-methacryloxy propyltris(trimethylsiloxy)silane, 3-acryloxy propyltris(trimethylsiloxy)silane, 3-acrylamide propyltris(trimethylsiloxy)silane, 3-methacrylamide propyltris(trimethylsiloxy)silane, 3-vinylacrylamide propyltris(trimethylsiloxy)silane, a-acrylamidopropyl-ω-butylpolydimethylsiloxane, or a combination thereof.

[0073] The present disclosure provides a contact lens that blocks blue light formed from a cured composition. The composition comprises a blue light blocking component, at least one hydrophilic monomer, a crosslinker, and a starter. The blue light blocking component is formed from a mixture or reaction of glycerol monomethacrylate (GMMA) and a yellow dye. In some embodiments, the contact lens is a hydrogel contact lens or a silicone hydrogel contact lens. In some embodiments, the composition further comprises a silicon-containing monomer.

[0074] In some embodiments, the yellow dye is selected from the group consisting of Reactive Yellow 15, Reactive Yellow 86, and Pigment Yellow 83. In some embodiments, the yellow dye is 0.01 wt% to 2 wt% based on 100 wt% of the composition. The yellow dye is, for example, 0.01, 0.05, 0.1, 0.5, 1, 1.5, or 2 wt%. When the weight percentage falls within the above range, the contact lenses have good color development and good blue light blocking rate, and the wearers can still maintain good visual perception.

[0075] In some embodiments, the weight ratio of the yellow dye to the glycerol monomethacrylate is 1:0.1 to 1:10. The weight ratio is, for example, 1:0.1, 1:0.5, 1:1, 1:2, 1:5, or 1:10. When the weight ratio falls within the above range, the yellow dye has good solubility and good compatibility in the composition, so that the contact lenses have good color development and good blue light blocking rate.

[0076] The present disclosure provides a method for preparing the blue light blocking contact lenses of any of the preceding embodiments, comprising the following operations. The glycerol monomethacrylate and the yellow dye are mixed to form a mixture. The mixture is heated to 25°C to 80°C for 0.5 hours to 24 hours to form a blue light blocking component. The composition containing the blue light blocking component, at least one hydrophilic monomer, a crosslinking agent, and a starter is cured to form the contact lenses. In some embodiments, the temperature for heating the mixture is 25, 35, 45, 55, 65, 75, or 80°C. In some embodiments, the heating time of the mixture is 0.5, 1, 5, 10, 15, 20, or 24 hours. The curing operation is described in the preceding embodiments and will not be repeated here.

[0077] In some embodiments, the method further comprises: before heating the mixture to 25°C to 80°C, adding a basic substance and an inhibitor to the mixture. In some embodiments, the pH value of the mixture is 10 to 14. The pH value is, for example, 10, 11, 12, 13, or 14. In some embodiments, the inhibitor comprises hydroquinone monomethyl ether. In some embodiments, the basic substance comprises sodium hydroxide. In some embodiments, the mixture does not contain the basic substance and the inhibitor. In some embodiments, the mixture does not contain water. Under the same experimental conditions of the amount of dye added, the reaction is carried out in a water-free environment, which can make the blue light blocking rate of the lenses higher; on the other hand, the reaction is carried out in a water-containing environment, which can make the blue light blocking rate of the lenses lower. In some embodiments, the contact lenses are hydrogel contact lenses or silicone hydrogel contact lenses. The advantages of the above-mentioned embodiments of treating the yellow dye with GMMA are described in the preceding embodiments regarding the first mixture and will not be repeated here.

[0078] The features of the present disclosure will be described more particularly below with reference to experimental examples. Although the following experimental examples are described, the materials used, their amounts and ratios, the details of the processes, and the process flow, etc. can be changed as appropriate without exceeding the scope of the present disclosure. Therefore, the present disclosure should not be interpreted restrictively from the experimental examples described below.

[0079] Experimental Example: Manufacturing of Contact Lenses

[0080] Manufacturing of contact lenses includes the following operations: injecting the blue light blocking contact lens hydrogel or silicone hydrogel composition into the interlayer of the male and female molds, polymerizing the composition by ultraviolet light, and curing to form a solid lens. After the solid lens is removed, it is hydrated and then sealed in a contact lens packaging solution and subjected to high-temperature sterilization treatment (125°C, 30 minutes) to complete the manufacturing of the blue light blocking multi-colored contact lens.

[0081] The blue light blocking contact lens hydrogel composition comprises one or more than one hydrophilic monomer, a blue light blocking component, a crosslinking agent, and a initiator. The blue light blocking contact lens silicone hydrogel composition comprises one or more than one hydrophilic monomer, a blue light blocking monomer, a crosslinking agent, a initiator, and a silicon-containing monomer. The hydrophilic monomer includes GMMA, HEMA, or a combination thereof. The crosslinking agent includes ethylene glycol dimethacrylate. The initiator includes bis(2,4,6-trimethylbenzoyl)-phenyl phosphine oxide. The hydrogel or silicone hydrogel composition can further comprise one or two color components. The blue light blocking component includes a yellow dye pretreated by a “synthesis method” or a “mixing method”. The color component includes a green dye, a blue dye, an orange dye, a red dye, or a black dye pretreated by a “synthesis method” or a “mixing method”. The “synthesis method” is to heat a mixture containing the hydrophilic monomer glycerol monomethacrylate (GMMA), the dye, the alkaline substance sodium hydroxide (NaOH), and the inhibitor MeHQ at 25°C to 80°C for at least 12 hours. The “mixing method” is to heat a mixture containing the hydrophilic monomer glycerol monomethacrylate (GMMA) and the dye at 25°C to 80°C for at least 12 hours. In the “synthesis method”, the weight ratio of the dye to GMMA is 1:10, MeHQ is about 0.07wt%, and sodium hydroxide is about 1wt%.

[0082] Please refer to Table 1 and Table 2 below, which respectively list the ingredients and ratios of each composition in Example 1 to Example 25, as well as the lenses prepared and their colors and blue light blocking rates. If the dye is pretreated by the “mixing method”, it is marked as M1; if the dye is pretreated by the “synthesis method”, it is marked as M2. Please refer to Figure 1 , Figure 1 The contact lenses obtained according to the preparation method of various embodiments of the present disclosure. Corresponding Figure 1 The transmittance spectrum of each lens is shown inFigures 2 to 7 . Figure 1 Including dark red lens R1, brownish red lens R2, orange red lens O1, orange lens O2, orange yellow lens O3, amber lens Y1, dark yellow lens Y2, yellow lens Y3, yellow-green lens G1, green lens G2, bright green lens G3, blue lens B1, gray-blue lens B2, indigo lens P1, purple lens P2, and gray lens G. Figure 1 The lenses correspond to the lenses of Examples 8 to 23 in Tables 1 and 2, respectively. Figures 2 to 7 Curves for the light absorption rates of the lenses mentioned above are shown as r1, r2, o1, o2, o3, y1, y2, y3, g1, g2, g3, b1, b2, p1, p2, and g, respectively, as well as the light absorption rate curve BLANK for the blank group lenses without dye. Figure 1 It is known that the disclosed content can be used to create multicolored contact lenses with a variety of vibrant colors, which can combine blue light blocking effect with aesthetic appeal. The light transmittance of the contact lens is measured using an ultraviolet / visible spectrometer. The average blue light transmittance (T%) from 380 nm to 460 nm is calculated by the machine program, which is the average harmful blue light transmittance. Subtracting the average blue light transmittance (T%) from 100% yields the blue light blocking rate, i.e., the harmful blue light blocking rate, as shown in Tables 1 and 2. In other words, blue light blocking rate % = 100% - blue light transmittance (T%).

[0083] Table 1

[0084]

[0085]

[0086] Table 2

[0087]

[0088] As shown in Tables 1 and 2, the harmful blue light blocking rates of the blue light blocking contact lenses of Examples 1 to 25 range from 5.57% to 26.27%. Therefore, the blue light blocking contact lenses of this disclosure can substantially achieve a harmful blue light blocking rate of 5% to 30%. Examples 1 to 24 can produce hydrogel contact lenses, while Example 25 can produce silicone hydrogel contact lenses. Example 25, by adding approximately 0.100 wt% of the dye Reactive Yellow 15 and pretreating it using a synthetic method, can achieve a blue light blocking rate of 26.27% for the lens. This demonstrates that the pretreatment method of this disclosure can achieve better blue light blocking performance in silicone hydrogel composition systems.

[0089] The blocking rate of harmful blue light is mainly affected by the concentration of yellow dye and pretreatment, and less affected by other non-yellow dyes. Table 3 below lists the examples prepared using only reactive yellow 15.

[0090] Table 3

[0091]

[0092] Comparing Example 2 and Example 7, both lenses are yellow, and the content of reactive yellow 15 is about 0.150wt%. Example 2 pretreated reactive yellow 15 by mixing method M1, and the blue light blocking rate of the lens is 13.05%, however, Example 7 pretreated reactive yellow 15 by synthetic method M2, and the blue light blocking rate of the lens can be greatly improved to 25.29%, which is 12.24% higher. In other words, the blue light blocking rate of Example 7 is about twice that of Example 2. Therefore, under the same proportion of yellow dye, pretreating the dye by synthetic method can greatly improve the blocking effect of harmful blue light of the lens.

[0093] Comparing Example 2 and Example 8, Example 8 only adds 0.085wt% of reactive yellow 15 and pretreats it by synthetic method M2, and the blue light blocking rate of the lens can reach 14.66%, and Example 2 adds 0.150wt% of reactive yellow 15 and pretreats it by mixing method M1, and the blue light blocking rate of the lens is 13.05%. Therefore, pretreating the dye by synthetic method can still make the lens have good blue light blocking rate with the addition of a small amount of dye. Comparing Example 8 with Example 2, the addition amount of Example 8 can be reduced by 0.065wt%, and during the hydration process, the product made by Example 8 can also reduce the dye washing dissolution amount and reduce the process wastewater. Comparing Example 6 and Example 7, if the lens needs to achieve a blue light blocking rate of 25%, Example 6 needs to use 0.301wt% of reactive yellow 15, while Example 7 only uses 0.150wt% of reactive yellow 15, and the addition amount can be reduced by 0.151wt%. Therefore, pretreating the dye by synthetic method can greatly improve the blocking effect of harmful blue light of the lens.

[0094] In summary, the present disclosure provides contact lenses with blue light blocking and methods of making the same. By pre-treating each color of dye with a hydrophilic monomer using a "synthesis method" or a "mixing method", and then mixing the pre-treated dye with other materials used to make contact lenses (e.g., other hydrophilic monomers, crosslinkers, initiators, or silicon-containing monomers) and then solidifying the mixture to form a lens, contact lenses with good color development and bright colors can be made, and the contact lenses also have good blue light blocking. Compared to the "mixing method", the "synthesis method" can more effectively improve the solubility and compatibility of the dye in the composition, and can further reduce process wastewater. Furthermore, the methods of the present disclosure can improve the feasibility of making multi-colored lenses by using combinations of multiple dyes.

[0095] While the present disclosure has been described in detail with respect to certain embodiments, other embodiments can exist. Accordingly, the spirit and scope of the appended claims should not be limited to the description of the embodiments contained herein.

[0096] It will be apparent to one of ordinary skill in the art that various modifications and variations can be made to the present disclosure without departing from the spirit or scope of the disclosure. Other embodiments of the present disclosure will be apparent to those skilled in the art from consideration of the specification and practice of the present disclosure. Therefore, it is intended that the present disclosure cover the modifications and variations of this disclosure.

Claims

1. A contact lens that blocks blue light, characterized in that, The contact lens is formed from a cured composition, the composition comprising: a blue light blocking component that is mixed or reacted from a first hydrophilic monomer and active yellow 15, active yellow 86, or pigment yellow 83; a first colored dye component that is mixed or reacted from a second hydrophilic monomer and a first colored dye, wherein the first colored dye comprises a green dye, a cyan dye, a blue dye, an orange dye, a red dye, a black dye, or a combination thereof, the first colored dye having a vinyl polymerizable group, a sulfonic acid group, a sulfonyl group, a sulfonate group, an amide group, or a combination thereof, when the first colored dye component is reacted from the second hydrophilic monomer and the first colored dye, the second hydrophilic monomer is selected from the group consisting of glycidyl methacrylate, glyceryl monomethacrylate, acrylic acid, N,N-dimethylacrylamide, and 2-methacryloyloxyethyl phosphorylcholine; at least one third hydrophilic monomer; a crosslinker; and a starter.

2. The contact lens of claim 1, wherein, The first and third hydrophilic monomers are independently selected from the group consisting of N-vinylpyrrolidone, 2-hydroxyethyl methacrylate, glycidyl methacrylate, glyceryl monomethacrylate, methacrylic acid, acrylic acid, N,N-dimethylacrylamide, N,N-diethylacrylamide, N-vinyl-N-methylacetamide, 2-methacryloyloxyethyl phosphorylcholine, and 2-hydroxybutyl methacrylate.

3. The contact lens of claim 1, wherein, The composition further comprises a second colored dye component that is mixed or reacted from a fourth hydrophilic monomer and a second colored dye, wherein the second colored dye comprises a green dye, a cyan dye, a blue dye, an orange dye, a red dye, a black dye, or a combination thereof.

4. The contact lens of claim 3, wherein, The fourth hydrophilic monomer is selected from the group consisting of N-vinylpyrrolidone, 2-hydroxyethyl methacrylate, glycidyl methacrylate, glyceryl monomethacrylate, methacrylic acid, acrylic acid, N,N-dimethylacrylamide, N,N-diethylacrylamide, N-vinyl-N-methylacetamide, 2-methacryloyloxyethyl phosphorylcholine, and 2-hydroxybutyl methacrylate.

5. The contact lens of claim 1, wherein, The active yellow 15, the active yellow 86, or the pigment yellow 83 is 0.01 wt% to 2 wt%, and the first colored dye is 0.01 wt% to 2 wt%, based on 100 wt% of the composition.

6. The contact lens of claim 1, wherein, The active yellow 15, the active yellow 86, or the pigment yellow 83 is 0.01 weight part to 2 weight parts, and the first colored dye is greater than 0 weight part and less than or equal to 2 weight parts.

7. The contact lens of claim 1, wherein, The weight ratio of the active yellow 15, the active yellow 86, or the pigment yellow 83 to the first hydrophilic monomer is 1:0.1 to 1:

10.

8. The contact lens of claim 1, wherein, The weight ratio of the first colored dye to the second hydrophilic monomer is 1:0.1 to 1:

10.

9. The contact lens of claim 1, wherein, The first colored dye is selected from the group consisting of reactive blue 4, reactive blue 19, reactive blue 21, reactive blue 69, reactive blue 163, reactive blue 246, reactive blue 247, reactive red 11, reactive red 180, reactive black, reactive orange 78, and pigment green.

10. A method of making the blue light blocking contact lens of claim 1, wherein, Further comprising: mixing the first hydrophilic monomer with the reactive yellow 15, the reactive yellow 86, or the pigment yellow 83 to form a first mixture; heating the first mixture to 25°C to 80°C for 0.5 hours to 24 hours to form the blue light blocking component; mixing the second hydrophilic monomer with the first colored dye to form a second mixture; heating the second mixture to 25°C to 80°C for 0.5 hours to 24 hours to form the first colored dye component; and curing the blue light blocking component, the first colored dye component, the at least one third hydrophilic monomer, the crosslinking agent, and the initiator.

11. The method of claim 10, wherein, Further comprising: before heating the first mixture to 25°C to 80°C, adding a basic substance and hydroquinone monomethyl ether to the first mixture.

12. The method of claim 10, wherein, Further comprising: before heating the second mixture to 25°C to 80°C, adding a basic substance and hydroquinone monomethyl ether to the second mixture.

13. A contact lens that blocks blue light, characterized in that, The contact lens is formed from a cured composition, the composition comprising: a blue light blocking component formed from mixing or reacting glycerol monomethacrylate with reactive yellow 15, reactive yellow 86, or pigment yellow 83; at least one hydrophilic monomer; a crosslinking agent; and an initiator.

14. The contact lens of claim 13, wherein, The reactive yellow 15, the reactive yellow 86, or the pigment yellow 83 is 0.01 wt% to 2 wt% based on 100 wt% of the composition.

15. The contact lens of claim 13, wherein, The weight ratio of the reactive yellow 15, the reactive yellow 86, or the pigment yellow 83 to the glycerol monomethacrylate is 1: 0.1 to 1:

10.

16. A method of making the blue light blocking contact lens of claim 13, wherein, Further comprising: mixing the glycerol monomethacrylate with the reactive yellow 15, the reactive yellow 86, or the pigment yellow 83 to form a mixture; heating the mixture to 25°C to 80°C for 0.5 hours to 24 hours to form the blue light blocking component; and curing the blue light blocking component, the at least one hydrophilic monomer, the crosslinking agent, and the initiator.

17. The method of claim 16, wherein, Further comprising: before heating the mixture to 25°C to 80°C, adding a basic substance and hydroquinone monomethyl ether to the mixture.

Images