KR20210009257A - Contact lenses for blocking blue light and methods of manufacturing the same - Google Patents

Abstract

The present invention relates to a contact lens for blocking blue light and a manufacturing method thereof, wherein the contact lens for blocking blue light includes ortho-benzoquinone. The method of the present invention manufactures the contact lens with ortho-benzoquinone by oxidizing a copolymer after a polyphenol monomer which is a substance having a blue light blocking function is chemically coupled to a lens base material composition, thereby effectively absorbing and blocking the blue light as well as ultraviolet rays.

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, and 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 and a method of manufacturing the same to form ortho-benzoquinone by oxidation.

Contact lenses have been widely used because they are mounted on the front of the eyeball, and have a wider field of view than glasses and can avoid cosmetic disadvantages caused by wearing glasses. Today, it is used for medical, professional, and cosmetic purposes. Medically, it is used when vision is not sufficiently corrected unless it is a contact lens. Occupationally, it is used when glasses are blurred or dangerous. Cosmetically, it is used for people who do not want to use glasses or for the purpose of changing the eye color by special treatment of the contact lens surface or making the pupils look clear and larger.

The eyeball is the tissue most affected by UV in the human body, and the influence of UV rays accumulates and damages the eyeball and surrounding tissues and can cause eye diseases such as cataract, photokeratitis, and macular degeneration. In order to prevent this, sunglasses or glasses that block UV rays are sometimes used, and contact lenses that have a UV blocking function that are already commercially available are also worn.

Blue light with high scattering property causes deterioration of image quality formed on the retina, and because of its high refractive index, 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 the visual cells. Recently, an increasing number of people complaining of reduced vision and eye fatigue due to excessive use of electronic display devices such as smartphones and TVs and exposed to blue light for a long period of time. Accordingly, the need for a contact lens capable of effectively blocking blue light is increasing, but the development of a contact lens capable of blocking blue light is still insignificant.

Conventionally, as a technology attempted to manufacture a general lens other than a contact lens, a method of blocking blue light by absorbing blue light by adding a brown or orange dye as a colorant has been used. However, when the above dye is used for a contact lens, a blue light blocking effect can be obtained, but low visibility may be induced due to a decrease in visible light transmittance. In addition, since a colorant such as a dye is physically mixed with the crosslinkable polymer constituting the contact lens, there is a disadvantage that the colorant is released from the contact lens over time. Therefore, when manufacturing a contact lens, it is necessary to develop a contact lens in which a blue light blocking material is chemically bonded through polymerization with a monomer, 2-hydroxyethyl methacrylate (HEMA).

However, conventionally, a dye was mainly used as a lens for blocking blue light, and a polyphenol monomer was copolymerized with 2-hydroxyethyl methacrylate (HEMA), and then oxidized to ortho-benzoquinone. benzoquinone) has not been reported to manufacture a contact lens having a blue light blocking function.

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

An object of the present invention is 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, comprising the step of oxidizing the copolymer to form ortho-benzoquinone, blue light blocking contact lens It is 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), by oxidizing the copolymer to ortho-benzo It is to provide a method for manufacturing a contact lens for blocking blue light, comprising the step of forming quinone (ortho-benzoquinone).

However, the problem to be solved by the present invention is not limited to the problems mentioned above, and other problems that are 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, a contact lens for blocking blue light including ortho-benzoquinone is provided.

According to one side, the contact lens may further include 2-methacryloyloxyethyl phosphorylcholine (MPC).

According to one side, the methacryloyloxyethyl phosphorylcholine (MPC) may contain 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. A method of manufacturing a contact lens for blocking blue light 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. A method of manufacturing a contact lens for blocking blue light is provided.

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

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

According to one side, the polyphenol monomer may be a polymerization group 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 (HEMA) or a silicone monomer.

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

According to one side, the (a) step, azobisisobutyronitrile (AIBN), benzoin methyl ether (Benzoin methyl ether, BME), benzoyl peroxide (Benzoyl peroxide, BPO), dimethoxyphenyl Acetophenone (DMPA) and 2,5-dimethyl-2,5-di-(2-ethylhexanoperoxy) hexane may include a polymerization reaction by any one polymerization initiator.

Since the contact lens of the present invention has an oxidized quinone type group, it can effectively absorb and block not only blue light but also ultraviolet rays, and in particular, it can more effectively absorb blue light in the wavelength band of 380 nm to 450 nm, which is harmful to eye cells. In addition, in the case of adding 2-methacryloyloxyethyl phosphorylcholine (MPC), a compound having high moisture content and biocompatibility, the moisture content of the contact lens and the hydrophilicity of the lens surface are improved to increase the fit of the contact lens. I can.

Using the manufacturing method of the present invention, polyphenol monomers such as dopamine and gallic acid are copolymerized with 2-hydroxyethyl methacrylate (HEMA), chemically bonded, and then oxidized to ortho-benzoquinone (ortho- benzoquinone) formed contact lenses can be prepared. Since it can be manufactured only by the process of oxidizing the material by putting the material at once and polymerizing it, immersing it in a buffer solution, the manufacturing process is simpler and more economical than the conventional one. In addition, the degree of blocking blue light can be controlled by adjusting the weight part of the polyphenol monomer used in the copolymerization. Moreover, since the oxidized polyphenol monomer is chemically bonded to form a copolymer, there is no problem of elution of the blue light blocking material, and the shelf life of the contact lens can be increased.

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

1 shows a structural formula of a dopamine monomer synthesis reaction according to an embodiment of the present invention.
2 shows the polymerization reaction structure of lens samples 1 to 3 according to an embodiment of the present invention.
3 shows the polymerization reaction structure of lens samples 4 to 6 according to an embodiment of the present invention.
4 is a check of the blue light absorption function of the 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 measurement of the blue light blocking rate and light transmittance of the lens samples 1 to 6 according to an embodiment of the present invention.
7 is a check of the blue light blocking ability before and after oxidation of a 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, exemplary 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 rights of the patent application is not limited or limited by these embodiments. It should 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 interpreted 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 this 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, a contact lens for blocking blue light including ortho-benzoquinone is provided.

The ortho-benzoquinone is an organic compound in the form of a quinone formed by oxidation of a polyphenol monomer, and specifically, a water-soluble polyphenol is oxidized. When the polyphenol is oxidized to form a quinone-type structure, the effect of absorbing blue light appears. The degree of absorption of blue light can be achieved by adjusting the weight part of the polyphenol monomer. In this case, the part by weight of the polyphenol monomer may be 0.5 to 1.5 parts by weight based on the copolymer constituting the contact lens when a dopamine monomer is used, but is not limited thereto, and depending on the type of the polyphenol monomer included during polymerization It is desirable to be controlled. The polyphenol monomer may be a monomer synthesized by introducing a polymerization group into a polyphenol precursor. Specifically, the polyphenol precursor may be any one selected from the group consisting of catechol and pyrogallol derivatives. 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, and 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 liquid organic compound that is easily polymerized with other substances and has a colorless viscosity. 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 a macromer or a prepolymer, and is a hydrophilic material having an ophthalmically acceptable water content. Specifically, the silicone monomers are etafilcon A, genfilcon A, gallyfilcon A, senofilcon A, lenefilcon A, lot Lafilcon A (lotrafilcon A), lotrafilcon B (lotrafilcon B), balafilcon A (balafilcon A), Compilcon A (comfilcon A), or may include any one or more of polymacon (polymacon), but limited to this It does not become.

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 trimetha. It may be any one of acrylates (TMPTMA), preferably ethylene glycol dimethacrylate (EGDMA), but is not limited thereto.

The blue light blocking contact lens may further include a polymerization initiator. At this time, 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, preferably azobisisobutyronitrile (AIBN), but is limited thereto. It is not.

According to one side, the contact lens may further include 2-methacryloyloxyethyl phosphorylcholine (MPC). 2-methacryloyloxyethyl phosphorylcholine (MPC) is a lipid analog material containing phospholipids, a component of cell membranes, and is a zwitterion synthesized to have both hydrophilic and hydrophobic properties at both ends. It is characterized by hydrophilicity and biocompatibility. Since methacryloyloxyethyl phosphorylcholine (MPC) contains a polymerizable vinyl group, it has the advantage of being able to prepare a block polymer by polymerizing with other monomers. In addition, when methacryloyloxyethyl phosphorylcholine (MPC) is applied to a contact lens, it acts as a lubricant on the surface of the contact lens by increasing the degree of protein non-adsorption by increasing the moisture content and decreasing the contact angle on the lens surface. It is possible to improve the fit of the lens by performing.

According to one side, the methacryloyloxyethyl phosphorylcholine (MPC) may contain 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, a contact angle of a contact lens not containing 2-methacryloyloxyethyl phosphorylcholine (MPC) may be 68 to 76, and the methacryloyloxy The contact angle of the contact lens including 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 a contact lens not containing methacryloyloxyethyl phosphorylcholine (MPC) may be 40% or more, and methacryloyloxyethyl phosphorylcholine (2-methacryloyloxyethyl phosphorylcholine) Phosphorylcholine, MPC) may have an average moisture content of 60% or more. Preferably, the average moisture content of the contact lens including 2-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, a blue light blocking contact lens that does not contain 2-methacryloyloxyethyl phosphorylcholine (MPC) may have a blue light blocking rate of 23 to 40 and a light transmittance of 84% or more. The blue light blocking contact lens containing 2-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 a phenomenon of severely distorting the color of an object may appear, it is preferable that the blue light blocking contact lens 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 ultraviolet rays. Specifically, ultraviolet rays in a wavelength band of 200 to 380 nm may be blocked, but the present invention is not limited thereto. Specifically, the contact lens may be the most ideal that the UV blocking rate is 100%, but the blue light blocking contact lens of the present invention may have a UV blocking rate of 50% or more within a range that does not affect the blue light blocking function, and 70% It is preferable that the above 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. A method of manufacturing a contact lens for blocking blue light 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. A method of manufacturing a contact lens for blocking blue light is provided.

The step (a) is a step of copolymerizing a lens, and polymerization may be performed by putting a substance participating in the copolymerization reaction at once. Specifically, each reactant may be quantitatively mixed so as to have a predetermined mixing ratio, and 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 lens-molding monomer into a lower mold, assembling the upper mold, 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 an advantage that does not require a separate bath, room temperature drying step, oven drying step, or the like. In addition, since polymerization is performed without using a solvent, there is little change in shape after polymerization, so there is an advantage in that the physical properties of the manufactured contact lens are less deteriorated. In this case, the polymerization may be performed in an oven at 90° C. for 4 hours.

According to one side, the oxidation may be performed by a Tris buffer solution having a pH of 8 to 10, and specifically, a pH of 9 is preferable, but the present invention is not limited thereto.

According to one side, the ortho-benzoquinon may be produced from the polyphenol monomer. Specifically, the copolymer formed in step (a) is immersed in the Tris buffer solution to oxidize the polyphenol monomer to form ortho-benzoquinone. In this case, the immersion time may be 20 to 26 hours, preferably 24 hours, but is not limited thereto. In addition, it is preferable to periodically check the pH during the step (b) and, if the pH is decreased, to maintain pH 9 by adding a Tris buffer solution.

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 the 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 a polymerization group 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 the present invention is not limited thereto. As an example, in the case of using dopamine as a 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, and specifically, the reaction shown in FIG. 1 Dopamine monomer can be synthesized as shown in the structural formula.

According to one side, the lens base composition may be a 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, the 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, the (a) step, azobisisobutyronitrile (AIBN), benzoin methyl ether (Benzoin methyl ether, BME), benzoyl peroxide (Benzoyl peroxide, BPO), dimethoxyphenyl Acetophenone (DMPA) and 2,5-dimethyl-2,5-di-(2-ethylhexanoperoxy) hexane may include a polymerization reaction by any one polymerization initiator. Specifically, it is preferable to use azobisisobutyronitrile (AIBN) as a polymerization initiator, but is not limited thereto.

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

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

Example

A contact lens for blocking blue light was prepared through a copolymerization and oxidation reaction of a polyphenol monomer and a 2-hydroxyethyl methacrylate (HEMA) monomer by the method of the present invention. Specifically, the contact lens for blocking blue light 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 contact lens for blocking blue light 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 500 ml flask (two-neck flask) 10 g 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, followed by ultrasonication 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, Solution 2 was prepared by adding 25 ml of tetrahydrofuran solvent to methacrylic anhydride. After slowly mixing Solutions 1 and 2 at 0° C., the mixture was stirred for 12 hours while maintaining the pH of 9 using 1M NaOH solution. Thereafter, the pH was converted to 1 to 2 using a 6N HCl solution, and then stirred for 1 hour again. The agitated solution was extracted with ethyl acetate, and recrystallized through hexane to synthesize a dopamine monomer with a polymerization group. The synthesis of the dopamine monomer was performed according to the reaction structure shown in FIG. 1, and the molecular structure of the synthesized dopamine monomer was confirmed through an NMR spectrometer.

Example 2. Manufacture of contact lens for blocking blue light

A lens sample was prepared by the method described later using the dopamine monomer prepared in Example 1. At this time, the dopamine monomer was mixed at a weight ratio of 0.5, 1, and 1.5 to the copolymer constituting the lens to prepare contact lenses of lens samples 1 to 3. Each reactant was quantified in the amount shown in Table 1 below, and the quantified substance was added to a 20ml vial, followed by ultrasonic treatment for 30 minutes to mix. Thereafter, the mixture was injected into a lower mold of polypropylene (PP), covered with polybutylene terephthalate (PBT), and polymerized in an oven at 90° C. for 4 hours. 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 50 ml of demineralized water was added 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 an oxidation reaction. The pH of the solution containing each sample was checked by time, and the degree of oxidation was checked through UV absorption. As the oxidation reaction proceeded, it was checked whether absorption increased in the wavelength region of blue light (380 to 450 nm), and when the pH decreased, a Tris buffer was additionally added to maintain pH 9. 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.

FIG. 2 is a reaction structural formula of lens samples 1 to 3 prepared by the above-described method. Referring to FIG. 2, when oxidizing using a Tris buffer solution as a final reaction, the hydroxy group of the benzene ring is modified and quinone You can see that the group was formed.

Meanwhile, lens samples 4 to 6 were prepared in the same manner as described above, except that MPC was added. At this time, the MPC was fixed at 7 parts by weight based on the copolymer constituting the contact lens, and the reactants were quantified and used 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 the reaction structure of the lens samples 4 to 6. Referring to FIG. 3, when oxidizing using a Tris buffer as a final reaction, the hydroxy group of the benzene ring is modified as in FIG. It can be seen that this was formed. In addition, when the prepared lens samples 1 to 6 were observed with the naked eye, as shown in FIG. 4, all of the lens samples 1 to 6 were in a brownish state, and from this, it was confirmed that all of the lens samples 1 to 6 were absorbing blue light.

Example 3. Measurement of moisture content of a lens sample

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, 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 equation, and the average value was derived by experimenting three times for each lens sample.

[expression]

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

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

1st moisture content 2nd moisture content 3rd 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

FIG. 5 is a comparison of lens contact angles of lens samples 1 to 3 without MPC added and lens samples 4 to 6 polymerized by adding MPC. Each of the lens samples was made flat, and water droplets were dropped thereon, and after about 1 minute, the contact angle was measured. As a result of the measurement, lens samples 1 to 3 without MPC had a lens water contact angle of 68 to 75, and lens samples 4 to 6 including MPC had a value of 51 to 58 degrees. That is, it was confirmed that lens samples 4 to 6 containing MPC had higher moisture content and increased hydrophilic surface compared to lens samples 1 to 3 not containing MPC.

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, a result similar to the graph of FIG. 6 was confirmed. In this case, as a control, a lens sample (HEMA-only) that did not contain a polyphenol monomer was used. 6 is a graph showing a UV absorption spectrum over time and a transmittance spectrum according to the spectrum result. Referring to FIGS. 6A and 6C, lens samples 1 to 6 are in the ultraviolet wavelength region (270 nm- 380nm) as well as in the blue light wavelength region (380nm-450nm). In addition, looking at (a) of FIG. 6, it can be seen that the absorption degree of samples 3 and 6 of the entire lens samples is relatively higher, and the absorption degree of blue light increases as the weight part of the polyphenol monomer increases I confirmed that it is. An average blue-light block ratio (RBL) at a wavelength of 380 to 450 nm can be defined from the spectra 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 rates in Table 3, it was confirmed that the blue light blocking rates 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 FIG. 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 an ultraviolet 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 that of the lens sample 3 decreased to 84%. Similarly, the light transmittance of the lens sample 4 was 90%, whereas the result was slightly reduced to 87% in the lens sample 6. 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 to which the blue light blocking rate is increased is greater than that of the decreasing value of the light transmittance, it has been verified that the blue light blocking effect is advantageous 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 are similar to those of the lens samples 1 to 3 without MPC. It was confirmed that it had a light transmittance.

Example 5. Measurement of UV blocking rate

The UV blocking rates of the 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 280nm-380nm existing in the atmosphere, lens samples 1 to 3 had a blocking rate of 52.9%, 67.1%, and 76.3%, respectively, and lens samples 4 to 6 were respectively 47.7% and 58.3 % And 71.5% of blocking rate were shown. In the same manner as the blue light blocking function of Example 4 described above, it was confirmed that the effective UV blocking function appeared in the lens samples 3 and 6 having a relatively high weight of the dopamine monomer.

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

In order to manufacture a contact lens for blocking blue light using a silicone lens substrate, the polymerized compound composition of Table 5 was used.

Silicone lens sample Lens base (silicone monomer) 30.0 wt% TRIS ^a + 10.0 wt% mPDMS ^b Polyphenolic 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 60° C. for 1 hour to prepare a silicone lens sample. Impurities were removed from the prepared silicon lens sample using distilled water and isopropyl alcohol.

Thereafter, after 50 ml of demineralized water was added 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 an oxidation reaction. After 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 a silicon lens sample for blocking blue light.

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

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

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

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

Using the silicon 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 spectra before and after oxidizing the silicon 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 visible light after oxidation. It can be seen that the absorption spectrum appears up to the wavelength range. It was confirmed that similar characteristics were also observed in the transmission spectrum. Referring to FIG. 8B, after oxidizing the silicon contact lens sample prepared in Example 6, it can be seen that the transmittance in the vicinity of the blue light region (380 to 450 nm) is significantly reduced. In addition, it was confirmed that the transmittance in the ultraviolet region corresponding to the wavelength regions of UV A and B (280 to 380 nm) was also reduced at the same time.

Previously, as 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 silicon contact lens sample prepared in Example 6, silicon oxidized with a Tris buffer solution as shown in Table 6 below. The contact lens sample had a blue light blocking rate of 59%, an average visible light transmittance (380 to 780 nm) of 79%, and a UV blocking rate of 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) containing, blue light blocking contact lenses. 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) comprises 5 to 10 parts by weight based on the copolymer constituting the contact lens, blue light blocking contact lens. The method of claim 1,
The contact lens has a contact angle of 50 to 80, a contact lens for blocking blue light. The method of claim 1,
The contact lens, a contact lens for blocking blue light having a water content of 40% or more. The method of claim 1,
The contact lens,
The blue light blocking rate is 20 to 45%,
A contact lens for blocking blue light with a light transmittance of 80% or more. The method of claim 6,
The blue light has a wavelength range of 380 to 450 nm, a contact lens for blocking blue light. The method of claim 1,
The contact lens is a contact lens for blocking blue light to block ultraviolet rays. (a) forming a copolymer of a polyphenol monomer and a lens base composition; And
(b) oxidizing the copolymer to form an ortho-benzoquinone, comprising the step of forming a contact lens for blocking blue light. (a) forming a copolymer of a polyphenol monomer, a lens base composition, and methacryloyloxyethyl phosphorylcholine (MPC); And
(b) oxidizing the copolymer to form an ortho-benzoquinone, comprising the step of forming a contact lens for blocking blue light. The method of claim 9 or 10,
The oxidation is a method of manufacturing a contact lens for blocking blue light by using a Tris buffer solution having a pH of 8 to 10. The method of claim 9 or 10,
The ortho-benzoquinon (ortho-benzoquinon) is produced from the polyphenol monomer, blue light blocking contact lens manufacturing method. The method of claim 9 or 10,
The polyphenol monomer, a polymerization group is introduced into any one selected from the group consisting of catechol and pyrogallol derivatives, a method of manufacturing a contact lens for blocking blue light. The method of claim 9 or 10,
The lens base composition is hydroxyethyl methacrylate (HEMA) or a silicone monomer, a method of manufacturing a contact lens for blocking blue light. The method of claim 9 or 10,
The step (a) includes ethylene glycol dimethacrylate (EGDMA), diethylene glycol methacrylate (DEGMA), glycerol dimethacrylate (GDMA), divinylbenzene (DVB), and trimethylolpropane. A method for manufacturing a contact lens for blocking blue light, comprising a polymerization reaction with any one of trimethacrylate (TMPTMA) crosslinking agent. The method of claim 9 or 10,
The (a) step is, 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 polymerization initiator, blue light blocking contact lens manufacturing method.

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