KR102259281B1 - Contact lenses for blocking blue light and methods of manufacturing the same - Google Patents

Abstract

To a contact lens for blocking blue light comprising ortho-benzoquinone and a method for manufacturing the same, after chemically bonding a polyphenol monomer, which is a blue light blocking material, to a lens base composition by the method of the present invention , it is possible to effectively absorb and block blue light as well as ultraviolet light by manufacturing a contact lens in which ortho-benzoquinone is formed by oxidation.

Description

Contact lenses for blocking blue light and methods of manufacturing the same

The present invention relates to a contact lens for blocking blue light containing ortho-benzoquinone and a method for manufacturing the same. Specifically, after forming a copolymer of a polyphenol monomer and a lens base composition, the copolymer It relates to a contact lens for blocking blue light that oxidizes to form ortho-benzoquinone and a method for manufacturing the same.

Contact lenses have been widely used because they have the advantage of being mounted on the front of the eyeball and having a wider field of view compared to glasses and avoiding cosmetic disadvantages caused by wearing glasses. Today, it is used for medical, occupational and cosmetic purposes. Medically, it is used when the vision cannot be corrected enough without contact lenses, and it is used when the glasses are cloudy or dangerous for work. Cosmetically, it is used for people who do not want to use glasses or for the purpose of changing the eye color or making the pupils appear clearer and bigger by special treatment of the contact lens surface.

The eye is the tissue most affected by UV in the human body, and the effects of UV light accumulate and damage the eye and surrounding tissues, and may cause eye diseases such as cataracts, photokeratitis, and macular degeneration. In order to prevent this, sunglasses or glasses with a UV blocking function are sometimes used, and contact lenses with an already commercialized UV blocking function are also worn.

Blue light with high scattering property causes deterioration of the image quality on the retina, and since the refractive index is large, chromatic aberration occurs due to the image formed in front of the retina, which can cause eye fatigue and glare. In addition, since the energy is high among the wavelengths of visible light, it may adversely affect photoreceptor cells. Recently, the number of people who are exposed to blue light for a long period of time due to excessive use of electronic display devices such as smart phones and TVs is increasing, and people complaining of reduced eyesight and eye fatigue. Accordingly, the need for contact lenses capable of effectively blocking blue light is increasing, but development of contact lenses capable of blocking blue light is still insignificant.

Conventionally, as a technique attempted to manufacture a general lens other than a contact lens, a method of blocking blue light by absorbing blue light by adding a dye having a brown or orange color as a colorant was used. However, when the above dye is used in a contact lens, a blue light blocking effect may be obtained, but low visibility may be caused due to a decrease in visible light transmittance. In addition, since the colorant such as dye is included in a physically mixed state with the crosslinkable polymer constituting the contact lens, there is a disadvantage that is released from the contact lens over time. Therefore, it is necessary to develop a contact lens in which a blue light blocking material is chemically combined with hydroxyethyl methacrylate (HEMA) as a monomer during the manufacture of contact lenses.

However, in the prior art, a dye was mainly used as a lens for blocking blue light, and a polyphenol monomer was copolymerized with hydroxyethyl methacrylate (HEMA) and then oxidized to ortho-benzoquinone (ortho- benzoquinone). A technique for manufacturing a contact lens having a blue light blocking function by forming benzoquinone) has not been reported.

Patent Document 1. Korea Patent Publication No. 2017-0105452 Patent Document 2. International Publication No. 2016-175619

It is an object of the present invention to provide a contact lens for blocking blue light containing ortho-benzoquinone.

Another object of the present invention is to form a copolymer of a polyphenol monomer and a lens base composition, oxidizing the copolymer to form ortho-benzoquinone, a blue light blocking contact lens comprising the steps of: To provide a manufacturing method.

Another object of the present invention is to form a copolymer of a polyphenol monomer, a lens base composition, and methacryloyloxyethyl phosphorylcholine (MPC), oxidizing the copolymer to ortho-benzo It is to provide a method of manufacturing a contact lens for blocking blue light, comprising the step of forming a quinone (ortho-benzoquinone).

However, the problems to be solved by the present invention are not limited to the problems mentioned above, and other problems not mentioned will be clearly understood by those of ordinary skill in the art from the following description.

According to an embodiment of the present invention, ortho-benzoquinone (ortho-benzoquinone) is provided for blocking contact lenses for blue light.

According to one side, the contact lens may further include methacryloyloxyethyl phosphorylcholine (MPC).

According to one side, the methacryloyloxyethyl phosphorylcholine (2-methacryloyloxyethyl phosphorylcholine, MPC) may include 5 to 10 parts by weight based on the copolymer constituting the contact lens.

According to one side, the contact lens may have a contact angle of 50 to 80.

According to one side, the contact lens may have a moisture content of 40% or more.

According to one side, the contact lens may have a blue light blocking rate of 20 to 45%, and a light transmittance of 80% or more.

According to one side, the blue light may have a wavelength range of 380 to 450 nm.

According to one side, the contact lens may block ultraviolet rays.

According to another embodiment of the present invention, forming a copolymer of a polyphenol monomer and a lens base composition; And (b) oxidizing the copolymer to form ortho-benzoquinone (ortho-benzoquinone), comprising the step of forming a blue light blocking contact lens manufacturing method is provided.

According to another embodiment of the present invention, (a) forming a copolymer of a polyphenol monomer, a lens base composition, and methacryloyloxyethyl phosphorylcholine (MPC); And (b) oxidizing the copolymer to form ortho-benzoquinone (ortho-benzoquinone), comprising the step of forming a blue light blocking contact lens manufacturing method is provided.

According to one side, the oxidation may be by a Tris buffer solution having a pH of 8 to 10.

According to one side, the ortho-benzoquinone (ortho-benzoquinon) may be one produced from the polyphenol monomer.

According to one side, the polyphenol monomer may be one in which a polymerization group is introduced into any one selected from the group consisting of catechol and pyrogallol derivatives.

According to one side, the lens base composition may be hydroxyethyl methacrylate (2-hydroxyethyl methacrylate, HEMA) or a silicone monomer.

According to one side, in step (a), ethylene glycol dimethacrylate (EGDMA), diethylene glycol methacrylate (DEGMA), glycerol dimethacrylate (GDMA), divinylbenzene (DVB) ) and trimethylolpropane trimethacrylate (TMPTMA).

According to one side, in the step (a), azobisisobutyronitrile (AIBN), benzoin methyl ether (BME), benzoyl peroxide (Benzoyl peroxide, BPO), dimethoxyphenyl A polymerization reaction using any one of acetophenone (DMPA) and 2,5-dimethyl-2,5-di-(2-ethylhexanoperoxy)hexane may be included.

Since the contact lens of the present invention has an oxidized quinone-type group, it can effectively absorb and block ultraviolet light as well as blue light, and in particular, it can more effectively absorb blue light in a wavelength band of 380 nm to 450 nm, which is harmful to eye cells. In addition, when methacryloyloxyethyl phosphorylcholine (MPC), a compound with high moisture content and biocompatibility, is added, the moisture content of the contact lens and the hydrophilicity of the lens surface are improved to increase the wearing comfort of the contact lens. can

Using the manufacturing method of the present invention, polyphenol monomers such as dopamine and gallic acid are chemically bonded by copolymerizing with hydroxyethyl methacrylate (HEMA), and then oxidized to ortho-benzoquinone (ortho- benzoquinone). It is possible to manufacture contact lenses in which benzoquinone) is formed. It can be manufactured only by adding materials at once and polymerizing them, then immersing them in a buffer to oxidize them, so the manufacturing process is simpler and more economical than conventional ones. In addition, the degree of blocking of blue light can be controlled by adjusting the weight part of the polyphenol monomer used for copolymerization. Furthermore, since the oxidized polyphenol monomer is chemically combined to form a copolymer, there is no problem of dissolution of the blue light blocking material, and thus the shelf life of the contact lens can be extended.

However, the effects of the present invention are not limited to the above-described effects, and it should be understood to include all effects that can be inferred from the configuration of the invention described in the detailed description or claims of the present invention.

1 shows a structural formula of dopaminergic monomer synthesis according to an embodiment of the present invention.
2 is a view showing polymerization reaction structural formulas of lens samples 1 to 3 according to an embodiment of the present invention.
3 shows the polymerization reaction structural formulas of lens samples 4 to 6 according to an embodiment of the present invention.
4 shows the blue light absorption function of lens samples 1 to 6 according to an embodiment of the present invention.
5 is a measurement of lens contact angles of lens samples 1 to 6 according to an embodiment of the present invention.
6 is a view showing measurements of blue light blocking rate and light transmittance of lens samples 1 to 6 according to an embodiment of the present invention.
Figure 7 confirms the blue light blocking ability before and after oxidation of the silicon contact lens according to an embodiment of the present invention.
8 is a measurement of blue light blocking rate (absorption rate) and light transmittance before and after oxidation of a silicon contact lens according to an embodiment of the present invention.

Hereinafter, embodiments will be described in detail with reference to the accompanying drawings. However, since various changes may be made to the embodiments, the scope of the patent application is not limited or limited by these embodiments. It is to be understood that all changes, equivalents, or substitutes to the embodiments are included in the scope of the rights.

The terms used in the examples are used for illustrative purposes only and should not be construed as limiting. Singular expressions include plural expressions unless the context clearly indicates otherwise. In the present specification, terms such as "comprise" or "have" are intended to designate the presence of features, numbers, steps, actions, components, parts, or combinations thereof described in the specification, but one or more other features. It is to be understood that the presence or addition of elements or numbers, steps, actions, components, parts, or combinations thereof does not preclude in advance.

Unless otherwise defined, all terms used herein, including technical or scientific terms, have the same meaning as commonly understood by one of ordinary skill in the art to which the embodiment belongs. Terms as defined in a commonly used dictionary should be interpreted as having a meaning consistent with the meaning in the context of the related technology, and should not be interpreted as an ideal or excessively formal meaning unless explicitly defined in the present application. Does not.

In addition, in the description with reference to the accompanying drawings, the same reference numerals are assigned to the same components regardless of the reference numerals, and redundant descriptions thereof will be omitted. In describing the embodiments, when it is determined that a detailed description of related known technologies may unnecessarily obscure the subject matter of the embodiments, the detailed description thereof will be omitted.

According to an embodiment of the present invention, ortho-benzoquinone (ortho-benzoquinone) is provided for blocking contact lenses for blue light.

The ortho-benzoquinone (ortho-benzoquinone) is a quinone-type organic compound formed by oxidation of a polyphenol monomer, specifically, an oxidized form of a water-soluble polyphenol. When the polyphenol is oxidized to form a quinone-type structure, the effect of absorbing blue light appears. The degree of absorbing blue light is possible by adjusting the weight part of the polyphenol monomer. At this time, the weight part of the polyphenol monomer, when using the dopamine monomer, may be 0.5 to 1.5 parts by weight based on the copolymer constituting the contact lens, but is not limited thereto, depending on the type of polyphenol monomer included during polymerization Controlled is preferred. The polyphenol monomer may be a monomer synthesized by introducing a polymerization group to the polyphenol precursor. Specifically, the polyphenol precursor may be any one selected from the group consisting of catechol and pyrogallol derivatives, and in this case, the catechol derivative may be dopamine, and pyrogallol ) the derivative may be gallic acid.

The blue light blocking contact lens may further include a lens base composition, in this case, the lens base composition may be hydroxyethyl methacrylate (HEMA) or a silicone monomer, but is not limited thereto. . The hydroxyethyl methacrylate (2-Hydroxyethyl methacrylate, HEMA) is a colorless, viscous liquid organic compound that readily polymerizes with other substances. Hydroxyethyl methacrylate is used as a main material for hydrophilic contact lenses, and has relatively excellent physical properties including mechanical properties.

The silicone monomer contains two or more [-Si-O-] repeating units in the macromer or prepolymer, and is a hydrophilic material having an ophthalmically acceptable water content. Specifically, the silicone monomer is etafilcon A (etafilcon A), genfilcon A (genfilcon A), galyfilcon A (galyfilcon A), senofilcon A (senofilcon A), lenefilcon A (lenefilcon A), lot It may include any one or more of lotrafilcon A, lotrafilcon B, balafilcon A, comfilcon A, or polymacon, but is limited thereto. it's not going to be

The blue light blocking contact lens may further include a crosslinking agent. In this case, the crosslinking agent is ethylene glycol dimethacrylate (EGDMA), diethylene glycol methacrylate (DEGMA), glycerol dimethacrylate (GDMA), divinylbenzene (DVB), and trimethylolpropane trimeta. It may be any one of acrylate (TMPTMA), preferably ethylene glycol dimethacrylate (EGDMA), but is not limited thereto.

The blue light blocking contact lens may further include a polymerization initiator. In this case, the polymerization initiator is azobisisobutyronitrile (AIBN), benzoin methyl ether (BME), benzoyl peroxide (BPO), dimethoxyphenyl acetophenone (DMPA) and It may be any one of 2,5-dimethyl-2,5-di-(2-ethylhexanoperoxy)hexane, and preferably azobisisobutyronitrile (AIBN), but is limited thereto. it is not

According to one side, the contact lens, methacryloyloxyethyl phosphorylcholine (2-methacryloyloxyethyl phosphorylcholine, MPC) may be further included. Methacryloyloxyethyl phosphorylcholine (MPC) is a lipid analog material containing phospholipids, a component of the cell membrane. It is a zwitterion synthesized to have both hydrophilic and hydrophobic properties at both ends. It has the characteristics of having hydrophilicity and biocompatibility. Since 2-methacryloyloxyethyl phosphorylcholine (MPC) contains a polymerizable vinyl group, it has the advantage of being able to prepare a block polymer by polymerization with other monomers. In addition, when methacryloyloxyethyl phosphorylcholine (MPC) is applied to contact lenses, it increases the degree of protein non-adsorption by increasing the moisture content and decreasing the contact angle on the lens surface, thereby acting as a lubricant on the surface of the contact lens. By performing this, it is possible to increase the wearing comfort of the lens.

According to one side, the methacryloyloxyethyl phosphorylcholine (2-methacryloyloxyethyl phosphorylcholine, MPC) may include 5 to 10 parts by weight based on the copolymer constituting the contact lens. Specifically, the methacryloyloxyethyl phosphorylcholine (MPC) preferably contains 7 parts by weight based on the copolymer constituting the contact lens, but is not limited thereto.

According to one side, the contact lens may have a contact angle of 50 to 80. Specifically, as shown in FIG. 5, the contact angle of a contact lens not containing methacryloyloxyethyl phosphorylcholine (MPC) may be 68 to 76, and the methacryloyloxy The contact angle of the contact lens containing ethyl phosphorylcholine (2-methacryloyloxyethyl phosphorylcholine, MPC) may be 51 to 58, but is not limited thereto.

According to one side, the contact lens may have a moisture content of 40% or more. Specifically, the average moisture content of contact lenses not containing methacryloyloxyethyl phosphorylcholine (MPC) may be 40% or more, and methacryloyloxyethyl phosphorylcholine (2-methacryloyloxyethyl) The average moisture content of contact lenses containing phosphorylcholine (MPC) may be 60% or more. Preferably, the average moisture content of the contact lens containing methacryloyloxyethyl phosphorylcholine (MPC) may be 65% or more, but is not limited thereto.

According to one side, the contact lens may have a blue light blocking rate of 20 to 45%, and a light transmittance of 80% or more. Specifically, contact lenses for blocking blue light that do not contain methacryloyloxyethyl phosphorylcholine (MPC) may have a blue light blocking rate of 23 to 40 and a light transmittance of 84% or more. A contact lens for blocking blue light containing methacryloyloxyethyl phosphorylcholine (MPC) may have a blue light blocking rate of 23 to 38 and a light transmittance of 87% or more, but is not limited thereto. In this case, the blue light blocking rate may be further increased by increasing the weight part of the polyphenol monomer included in the blue light blocking contact lens. However, as a result, since the phenomenon of distorting the color of an object may occur severely, the blue light blocking contact lens preferably has a blue light blocking rate of 30 to 40% and a light transmittance of 84% or more.

According to one side, the blue light may have a wavelength range of 380 to 450 nm. Specifically, the wavelength of 380 to 450 nm may be a wavelength range of harmful blue light that is particularly harmful to the eye.

According to one side, the contact lens may block UV rays. Specifically, it is possible to block ultraviolet rays in a wavelength band of 200 to 380 nm, but is not limited thereto. Specifically, the contact lens may ideally have a UV blocking rate of 100%, but the contact lens for blue light blocking of the present invention may have a UV blocking rate of 50% or more in a range that does not affect the blue light blocking function, and 70% The above is preferably, but is not limited thereto.

According to another embodiment of the present invention, forming a copolymer of a polyphenol monomer and a lens base composition; And (b) oxidizing the copolymer to form ortho-benzoquinone (ortho-benzoquinone), comprising the step of forming a blue light blocking contact lens manufacturing method is provided.

According to another embodiment of the present invention, (a) forming a copolymer of a polyphenol monomer, a lens base composition, and methacryloyloxyethyl phosphorylcholine (MPC); And (b) oxidizing the copolymer to form ortho-benzoquinone (ortho-benzoquinone), comprising the step of forming a blue light blocking contact lens manufacturing method is provided.

The step (a) is a step of copolymerizing the lens, and may be to put a material participating in the copolymerization reaction at once and perform polymerization. Specifically, each reactant may be quantified to have a predetermined mixing ratio and mixed, then injected into a mold and placed in an oven to perform polymerization. In this case, a method of performing polymerization may be a cast mold method. The cast mold method refers to a method of manufacturing a contact lens by injecting a monomer for lens molding into a lower mold, assembling an upper mold, and separating and removing the mold after the monomer is hardened. For example, the lower mold may be polypropylene (PP), and the upper mold may be polybutylene terephthalate (PBT).

Specifically, step (a) is a step of polymerization without using a solvent such as water or an organic solvent, and has the advantage that it does not require a separate bath, room temperature drying step, oven drying step, and the like. In addition, since polymerization is performed without using a solvent, there is little change in shape after polymerization, and thus, there is an advantage in that the physical properties of the manufactured contact lens are less deteriorated. At this time, the polymerization may be carried out in an oven at 90 ℃ for 4 hours.

According to one side, the oxidation may be by a Tris buffer solution of pH 8 to 10, specifically, preferably pH 9, but is not limited thereto.

According to one side, the ortho-benzoquinone (ortho-benzoquinon) may be one produced from the polyphenol monomer. Specifically, by immersing the copolymer formed in step (a) in the Tris buffer solution, and oxidizing the polyphenol monomer, ortho-benzoquinone can be formed. At this time, the immersion time may be 20 hours to 26 hours, preferably 24 hours, but is not limited thereto. In addition, it is preferable to periodically check the pH while performing step (b), and if the pH is decreased, additionally add a Tris buffer to maintain the pH of 9.

In the method of manufacturing a contact lens for blocking blue light of the present invention, it is preferable that the step of synthesizing a polyphenol monomer using a polyphenol precursor is preceded before performing step (a). Specifically, the polyphenol monomer can be synthesized by introducing a polymerization group into a polyphenol precursor. According to one side, the polyphenol monomer may be one in which a polymerization group is introduced into any one selected from the group consisting of catechol and pyrogallol derivatives. For example, the catechol derivative may be dopamine, and the pygalol derivative may be gallic acid, but is not limited thereto. For example, when using dopamine as the polyphenol precursor, the dopamine monomer preferably contains 0.5 to 5 parts by weight based on the copolymer constituting the contact lens, but is not limited thereto. Specifically, the reaction shown in FIG. A dopamine monomer can be synthesized as shown in the structural formula.

According to one side, the lens base composition may be hydroxyethyl methacrylate (HEMA) or a silicone monomer, but is not limited thereto. The lens base composition is preferably used selectively according to the mechanical properties and characteristics of the contact lens other than the blue light blocking function.

According to one side, in step (a), ethylene glycol dimethacrylate (EGDMA), diethylene glycol methacrylate (DEGMA), glycerol dimethacrylate (GDMA), divinylbenzene (DVB) ) and trimethylolpropane trimethacrylate (TMPTMA). Specifically, it is preferable to use ethylene glycol dimethacrylate (EGDMA) as a crosslinking agent, but is not limited thereto.

According to one side, in the step (a), azobisisobutyronitrile (AIBN), benzoin methyl ether (BME), benzoyl peroxide (Benzoyl peroxide, BPO), dimethoxyphenyl A polymerization reaction using any one of acetophenone (DMPA) and 2,5-dimethyl-2,5-di-(2-ethylhexanoperoxy)hexane may be included. Specifically, it is preferable to use azobisisobutyronitrile (AIBN) as a polymerization initiator, but is not limited thereto.

The method for manufacturing a contact lens for blocking blue light of the present invention may further include the steps of a generally known method for manufacturing a contact lens in addition to the above-described method. For example, wetting and disinfecting the manufactured contact lenses, if necessary; or packaging and sterilizing the contact lens; may further include.

A more detailed description will be given later through the following examples.

Example

A contact lens for blocking blue light was prepared by copolymerizing and oxidizing a polyphenol monomer with a hydroxyethyl methacrylate (HEMA) monomer by the manufacturing method of the present invention. Specifically, the blue light blocking contact lens according to an embodiment of the present invention was manufactured according to Examples 1 and 2 to be described later, and the physical properties of the blue light blocking contact lens manufactured through Examples 3 and 4 were verified.

Example 1. Preparation of dopamine-HEMA copolymer

Dopamine was selected as a polyphenol material, and a dopamine monomer was synthesized. In a 500ml flask (two-neck flask), 10g of Na ₂ B ₄ O _7· 10H ₂ O, 5 g of Na ₂ CO ₃ , and 200 mL of demineralized water were added and sonicated for 1 hour. Then, after filling with nitrogen, 5 g of dopamine was added and stirred for 30 minutes to prepare solution 1. Separately from solution 1, 25 ml of a tetrahydrofuran solvent was added to methacrylic anhydride to prepare a solution 2. After slowly mixing solutions 1 and 2 at 0° C., the mixture was stirred for 12 hours while maintaining pH 9 using 1 M NaOH solution. Thereafter, the pH was changed to 1 to 2 using a 6N HCl solution, followed by stirring again for 1 hour. The stirred solution was extracted with ethyl acetate and recrystallized from hexane to synthesize a dopamine monomer with a polymerization group. The synthesis of the dopamine monomer was performed by the reaction structural formula as shown in FIG. 1, and the molecular structure of the synthesized dopamine monomer was confirmed through NMR spectroscopy.

Example 2. Preparation of contact lenses for blocking blue light

A lens sample was prepared by the method described below using the dopamine monomer prepared in Example 1. At this time, the dopamine monomer was mixed in a weight ratio of 0.5, 1, and 1.5 to the copolymer constituting the lens, respectively, to prepare the contact lenses of lens samples 1 to 3. Each of the reactants was quantified in the same amount as in Table 1 below, the quantified material was put into a 20ml vial, and then the mixture was sonicated for 30 minutes. After that, the mixture was poured into a polypropylene (PP) lower mold, covered with an upper mold, polybutylene terephthalate (PBT), and placed in an oven at 90 ° C for 4 hours to polymerize. After the polymerization was completed, the polymerized samples were separated from the mold.

Lens Sample 1 Lens Sample 2 Lens Sample 3 HEMA 2.958g 2.943g 2.928g dopamine monomer 0.015g 0.03g 0.045g Crosslinking agent (EGDMA) 0.012g 0.012g 0.012g Photoinitiator (AIBN) 0.012g 0.012g 0.012g

After adding 50 ml of demineralized water to the vial, 5 g of Tris buffer was added to adjust the solution to pH 9, and then the polymerized samples were put into each vial to perform oxidation reaction. The pH of the solution containing each sample was checked by time, and the degree of oxidation was confirmed through UV absorption method. As the oxidation reaction proceeded, it was checked whether absorption increased in the wavelength region (380 to 450 nm) of blue light, and when the pH was decreased, a pH of 9 was maintained by additionally adding a Tris buffer. When the oxidation reaction elapsed for about 24 hours, it was confirmed that there was no change in the UV absorption spectrum and the oxidation reaction was terminated, thereby preparing lens samples 1 to 3, which are contact lenses for blocking blue light.

2 is a reaction structural formula of lens samples 1 to 3 prepared by the above-described method. Referring to FIG. 2, when oxidation is performed using a Tris buffer solution as a final reaction, the hydroxyl group of the benzene ring is modified to quinone. It can be seen that the group has been formed.

Meanwhile, lens samples 4 to 6 were prepared in the same manner as described above, except that MPC was added. At this time, MPC was fixed at 7 parts by weight based on the copolymer constituting the contact lens, and the reactants were quantified as shown in Table 2 below.

Lens Sample 4 Lens sample 5 Lens sample 6 HEMA 2.751g 2.763g 2.721g dopamine monomer 0.015g 0.03g 0.045g Crosslinking agent (EGDMA) 0.012g 0.012g 0.012g Photoinitiator (AIBN) 0.012g 0.012g 0.012g MPC (7wt%) 0.21g 0.21g 0.21g

3 is a reaction structural formula of lens samples 4 to 6, referring to FIG. 3, when oxidation using a Tris buffer solution as a final reaction, the hydroxyl group of the benzene ring is modified as in FIG. It can be seen that this is formed. In addition, when the prepared lens samples 1 to 6 were visually observed, they all turned brown as shown in FIG. 4 , and from this, it was confirmed that all of the lens samples 1 to 6 absorbed blue light.

Example 3. Measurement of moisture content of lens samples

The moisture content of the lens samples 1 to 6 prepared in Examples 1 and 2 was measured. Each of the lens samples 1 to 6 was immersed in an excess of water for 48 hours, then taken out to remove moisture from the surface, and then the hydrated mass was measured. At this time, the moisture content was calculated using the following formula, and the average value was derived by experimenting three times for each lens sample.

[expression]

Moisture content (%) = 100 × (hydrated lens weight - dry lens weight)/hydrated lens weight

As a result of measuring the moisture content, as shown in Table 3 below, the average moisture content of lens samples 1 to 3 was 40% or more, and it was confirmed that the average moisture content of lens samples 4 to 6 to which MPC was added was 64% or more.

1st round moisture content 2nd round moisture content 3rd round moisture content average moisture content Lens Sample 1 43.0 43.4 41.4 42.6 Lens Sample 2 46.3 41.2 40.5 42.7 Lens Sample 3 41.4 43.8 37.4 40.9 Lens Sample 4 61.2 66.4 66.8 64.8 Lens sample 5 66.6 66.0 66.7 66.4 Lens sample 6 64.9 64.0 68.8 65.9

5 is a comparison of lens contact angles of lens samples 1 to 3 without adding MPC and lens samples 4 to 6 polymerized with MPC. After each lens sample was flattened and water droplets were dropped on it, the contact angle was measured after about 1 minute. As a result of the measurement, lens samples 1 to 3 without MPC had a water contact angle of 68 to 75, and lens samples 4 to 6 including MPC showed values of 51 to 58 degrees. That is, it was confirmed that, compared to lens samples 1 to 3 without MPC, lens samples 4 to 6 including MPC had a high water content and an increased hydrophilic surface.

Example 4. Measurement of blue light blocking rate

As a result of measuring the blue light blocking rate of the lens samples 1 to 6 prepared in Examples 1 to 2, the same results as in the graph of FIG. 6 were confirmed. At this time, as a control, a lens sample (HEMA-only) not containing a polyphenol monomer was used. 6 is a graph showing the UV absorption spectrum according to time and the transmittance spectrum according to the spectrum result. Referring to FIGS. 6 (a) and (c), lens samples 1 to 6 are in the ultraviolet wavelength region (270 nm-) compared to the control group. 380 nm) as well as it can be seen that absorption increases in the blue light wavelength region (380 nm-450 nm). In addition, referring to (a) of FIG. 6 , it can be seen that samples 3 and 6 have a relatively higher degree of absorption among all lens samples, and through this, the degree of absorption of blue light increases with the increase of the weight part of the polyphenol monomer. confirmed that it does. An average blue-light block ratio (RBL) at a wavelength of 380 to 450 nm can be defined from the spectrum of FIGS. 6A and 6C , and the results are shown in Table 4 below.

Blue light blocking rate
(blue-light block ratio, %) Light (visible light) transmittance
(Luminous Transmittance (τ)) Lens Sample 1 23% 92% Lens Sample 2 30% 89% Lens Sample 3 40% 84% Lens Sample 4 23% 90% Lens sample 5 29% 89% Lens sample 6 38% 87%

Looking at the blue light blocking rate of Table 3, it was confirmed that the blue light blocking rate of lens samples 3 and 6 having a relatively high content of dopamine monomer increased to 40% and 38%, respectively. In addition, as shown in (a) and (c) of Figure 6, by confirming a high UV absorption spectrum even in the range of the ultraviolet wavelength, it was verified that the lens samples 1 to 6 also have a UV blocking function. On the other hand, as a result of measuring the light transmittance in the visible light wavelength range, it was shown as (b) and (d) of FIG. 6 . Specifically, as shown in Table 4, the light transmittance of the lens sample 1 was 92%, whereas the lens sample 3 decreased to 84%. Similarly, the light transmittance of the lens sample 4 was 90%, whereas the lens sample 6 had a slightly reduced result to 87%. That is, it can be seen that the blue light blocking rate increases, but the light transmittance slightly decreases due to the increase in the content of the dopamine monomer having a blue light blocking function. However, since the degree of increase in the blue light blocking rate is greater than the decreasing value of the light transmittance, it was verified that the blue light blocking effect is desirable even with a slight decrease in the light transmittance. In addition, in the case of lens samples 4 to 6 containing MPC, the blue light blocking rate and light transmittance similar to those of lens samples 1 to 3 without MPC were shown. It was confirmed that it has light transmittance.

Example 5. Measurement of UV protection rate

UV blocking rates of lens samples 1 to 6 prepared in Examples 1 to 2 were measured. As a result of measuring the blocking rates of UV A and B in the range of 280 nm to 380 nm in the air, lens samples 1 to 3 had blocking rates of 52.9%, 67.1%, and 76.3%, respectively, and lens samples 4 to 6 were 47.7% and 58.3, respectively. %, showed a blocking rate of 71.5%. It was confirmed that effective UV blocking function appeared in lens samples 3 and 6 having a relatively high weight portion of dopamine monomer, similar to the blue light blocking function of Example 4 described above.

Example 6. Preparation of silicone contact lenses for blocking blue light

In order to prepare a contact lens for blocking blue light using a silicone lens substrate, the composition of the polymer compound shown in Table 5 below was used.

silicone lens sample Lens substrate (silicone monomer) 30.0 wt % TRIS ^a + 10.0 wt % mPDMS ^b polyphenol monomer 1.5wt% dopamine monomer Crosslinking agent 0.4 wt% EGDMA ^c Photoinitiator 0.15 wt% V-65 ^d other additives 9.0 wt% DMA ^e +43.95 wt% MVAc ^f +5.0% wt% MPC ^g

a: 3-[tris(trimethylsiloxy)silyl]propyl methacrylateb: methacryloxypropyl terminated polydimethylsiloxane

c: ethylene glycol dimethacrylate

d: 2,2'-azobis (2,4-dimethylvaleronitrile)

e: N,N-dimethylacrylamide

f: N-methyl-N-vinylacetamide

g: 2-methacryloyloxyethyl phosphorylcholine

After mixing the raw materials according to the composition ratio of the silicone lens sample in Table 3, the mixture was stirred at room temperature for 1 hour. The mixed monomer was injected into a contact lens mold and polymerized in a drying oven (HST-501S, Hanst) at 50° C. for 1 hour and at 60° C. for 1 hour to prepare a silicone lens sample. Impurities were removed from the prepared silicone lens sample using distilled water and isopropyl alcohol.

Thereafter, 50 ml of demineralized water was put into the vial, and then the solution was adjusted to pH 9 by adding 5 g of Tris buffer, and then the polymerized samples were put into each vial to perform oxidation reaction. After the oxidation reaction had elapsed for about 24 hours, it was confirmed that there was no change in the UV absorption spectrum and the oxidation reaction was terminated to prepare a blue light blocking silicone lens sample.

Example 7. Verification of blue light blocking effect of silicone contact lenses for blocking blue light I

Using the silicone contact lens sample prepared in Example 6, the color change of the silicone contact lens before and after oxidation with a Tris buffer solution of pH 9 was observed.

As a result of observation, as shown in FIG. 7 , it was confirmed that the silicone lens sample, which was transparent and colorless before immersion in the Tris buffer solution, changed to a transparent brown color after immersion in the Tris buffer solution. Through this, it can be seen that the silicon lens sample has blue light blocking ability by oxidation in the Tris buffer solution.

Example 8. Verification of blue light blocking effect of silicone contact lenses for blocking blue light II and verification of UV blocking effect

Using the silicone contact lens sample prepared in Example 6, the degree of absorption and blocking of blue light was confirmed through UV-vis absorption and transmission spectrum measurement. As a result of comparing the absorption spectrum before and after oxidation of the silicone contact lens sample with the Tris buffer solution, as shown in FIG. 8(a), the absorption spectrum appeared only in the UV wavelength region before oxidation, but after oxidation, visible light It can be seen that the absorption spectrum appears up to the wavelength range. It was confirmed that similar characteristics appeared in the transmission spectrum. Referring to (b) of FIG. 8 , it can be seen that the transmittance in the vicinity of the blue light region (380 to 450 nm) is significantly reduced after the silicon contact lens sample prepared in Example 6 is oxidized. In addition, it was confirmed that the transmittance in the ultraviolet region corresponding to the wavelength region (280 to 380 nm) of UV A and B also decreased at the same time.

As previously verified in Examples 4 and 5, as a result of measuring the blue light blocking rate, visible light transmittance and UV blocking rate of the silicone contact lens sample prepared in Example 6, the silicone oxidized with Tris buffer solution as shown in Table 6 below The blue light blocking rate of the contact lens sample was 59%, the average visible light transmittance (380 to 780 nm) was 79%, and the UV blocking rate was 94%.

Blue light blocking rate
(380-450nm) UV blocking rate
(280-380nm) Light (visible light) transmittance
(380-780nm) silicon
contact lenses
Sample 59% 94% 79%

As described above, although the embodiments have been described by the limited drawings, a person of ordinary skill in the art can apply various technical modifications and variations based on the above. For example, even if the described techniques are performed in a different order from the described method, and/or the described components are combined or combined in a form different from the described method, or are replaced or substituted by other components or equivalents. Appropriate results can be achieved.

Therefore, other implementations, other embodiments, and claims and equivalents fall within the scope of the following claims.

Claims (16)

Ortho-benzoquinone (ortho-benzoquinone), including a blue light blocking contact lens,
The contact lens is
Blue light blocking rate is 20 to 45% and light transmittance is 80%,
A contact lens for blocking blue light that absorbs blue light with a wavelength of 390 to 450 nm. The method of claim 1,
The contact lens, methacryloyloxyethyl phosphorylcholine (2-methacryloyloxyethyl phosphorylcholine, MPC) further comprising a blue light blocking contact lens. The method of claim 2,
The methacryloyloxyethyl phosphorylcholine (2-methacryloyloxyethyl phosphorylcholine, MPC) is a blue light blocking contact lens comprising 5 to 10 parts by weight based on the copolymer constituting the contact lens. The method of claim 1,
The contact lens, the contact angle of 50 to 80, a blue light blocking contact lens. The method of claim 1,
The contact lens, the moisture content of 40% or more, a contact lens for blocking blue light. delete delete The method of claim 1,
The contact lens, blocking ultraviolet rays, contact lenses for blocking blue light. (a) forming a copolymer of a polyphenol monomer and a lens base composition; and
(b) oxidizing the copolymer to form ortho-benzoquinone, a blue light blocking contact lens manufacturing method comprising the steps of:
The contact lens is
Blue light blocking rate is 20 to 45% and light transmittance is 80% or more,
A method of manufacturing a contact lens for blocking blue light, which absorbs blue light having a wavelength of 390 to 450 nm. (a) forming a copolymer of a polyphenol monomer, a lens base composition, and methacryloyloxyethyl phosphorylcholine (MPC); and
(b) oxidizing the copolymer to form ortho-benzoquinone, a blue light blocking contact lens manufacturing method comprising the steps of:
The contact lens is
Blue light blocking rate is 20 to 45% and light transmittance is 80% or more,
A method of manufacturing a contact lens for blocking blue light, which absorbs blue light having a wavelength of 390 to 450 nm. The method of claim 9 or 10,
The oxidation is a blue light blocking contact lens manufacturing method by a Tris buffer solution (Tris buffer) of pH 8 to 10. The method of claim 9 or 10,
The ortho-benzoquinone (ortho-benzoquinone) is produced from the polyphenol monomer, a blue light blocking contact lens manufacturing method. The method of claim 9 or 10,
The polyphenol monomer is a method for producing a contact lens for blocking blue light, wherein a polymerization group is introduced into any one selected from the group consisting of catechol and pyrogallol derivatives. The method of claim 9 or 10,
The lens base composition is hydroxyethyl methacrylate (2-hydroxyethyl methacrylate, HEMA) or a silicone monomer, a blue light blocking contact lens manufacturing method. The method of claim 9 or 10,
In step (a), ethylene glycol dimethacrylate (EGDMA), diethylene glycol methacrylate (DEGMA), glycerol dimethacrylate (GDMA), divinylbenzene (DVB) and trimethylolpropane Trimethacrylate (TMPTMA) comprising a polymerization reaction by any one of the crosslinking agent, a blue light blocking contact lens manufacturing method. The method of claim 9 or 10,
In the step (a), azobisisobutyronitrile (AIBN), benzoin methyl ether (BME), benzoyl peroxide (BPO), dimethoxyphenyl acetophenone (DMPA) And 2,5-dimethyl-2,5-di- (2-ethylhexanoperoxy) hexane comprising a polymerization reaction with any one of the polymerization initiator, blue light blocking contact lens manufacturing method.

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