KR102279488B1 - Blue light blocking contact lens using Tatrazine pigment and its manufacturing method - Google Patents

Abstract

The present invention relates to a soft contact lens capable of blocking blue light and a method for manufacturing the same. Particularly, the present invention relates to a blue light-blocking contact lens using a tartrazine pigment and a method for manufacturing the same, wherein tartrazine monomers capable of absorbing blue light in a wavelength region of 380-500 nm are copolymerized with starting material monomers used for manufacturing a hydrogel lens to protect an eyeball from blue light. According to the blue light-blocking contact lens using a tartrazine pigment and the method for manufacturing the same, it is possible to realize a light transmission of 90% or more in a wavelength region of 500 nm or more, and to reduce light transmission in a blue light region with a wavelength of 500 nm or less, while maintaining proper mechanical properties of a contact lens. In addition, tartrazine, which is an edible pigment, is used as a coloring agent to realize a blue light-blocking function and biocompatibility at the same time. Further, the method includes a simple process of linking a methacrylate polymerizable group to the carboxyl functional group of tartrazine and carrying out copolymerization with a material for a contact lens.

Description

Blue light blocking contact lens using Tatrazine pigment and its manufacturing method

The present invention relates to a soft contact lens that blocks blue light and a method for manufacturing the same, and more particularly, by copolymerizing a tartrazine monomer that absorbs blue light in the 380 to 500 nm region with a raw material monomer used when manufacturing a hydrogel lens. It relates to a blue light blocking contact lens using a tartrazine pigment that protects the eye from blue light when the lens is worn, and a method for manufacturing the same.

Visible light has a wavelength of 380 to 780 nm among all light rays, and refers to the area of light that can be detected by the human eye. Among them, visible light with the shortest wavelength, including violet and indigo, is blue light (380 to 500 nm). It is said Such blue light has a high energy, which adversely affects the photoreceptor cells, causes oxidative damage to intraocular proteins, and decreases the quality of images formed on the retina because of its high scattering properties, and chromatic aberration occurs due to the high refractive index, thereby increasing eye fatigue and glare.

If we look at the damage caused by the high scattering and refractive index of blue light in more detail, since blue light has high scattering properties, it is scattered by air particles or an ophthalmic medium, and the scattered light causes background noise to illuminate the entire retina, causing deterioration of image quality. , the chromatic aberration due to the high refractive index also deteriorates the quality of the image.

In recent years, due to the development of the IT industry, displays such as smartphones, tablets, computers, and TVs, which are frequently encountered, have a higher ratio of blue light than sunlight or fluorescent lamps to brighten the screen, so vision deterioration, fatigue, and headaches are aggravating. the current situation. In order to protect the eyes from such blue light, ophthalmic devices such as glasses and safety glasses include a blue light blocking function, but most contact lenses that are inconvenient to wear glasses or used for beauty do not have a blue light blocking function and do not have a blue light blocking effect. R&D and commercialization of contact lenses are also at a minimal level.

Looking at prior art related to contact lenses that block blue light, Korean Patent Application Laid-Open No. 10-2009-0036122 (April 13, 2009) discloses at least first and second concentric rings (pigmentation) in and around the central circular region of the contact lens. To provide a contact lens comprising an optical zone having a, wherein the central circular region and the second concentric ring substantially block transmission of UV light, blue light, or both, Korea Patent Registration No. 10-1786302 (2017.10.17) .) is a specific compound capable of absorbing blue light in a monomo composition that can produce soft contact lenses (4-[(2)-phenyldiazenyl]phenyl-2-methacrylate of Chemical Formula 1 (4-[ (E)-phenyldiazenyl]phenyl-2-methacrylate) or 2-{4-[(2)-phenyldiazenyl]phenoxy}ethyl-2-acrylate of Chemical Formula 2 (2-{4-[(E)) -phenyldiazenyl]phenoxy}ethyl-2-acrylate))) to reduce the transmittance of blue light passing through the contact lens, a method for manufacturing a blue light blocking soft contact lens and a soft contact lens manufactured using the same are provided.

Looking at the prior art, the first prior art is to perform coloring in a concentric ring on a general contact lens, which is substantially the same as a commonly used color lens, and gives a sense of heterogeneity to the eyeball when used due to the colorant used, and is applied to the outer periphery of the pupil. It is expected that the reduction rate of the transmittance of blue light is low as the concentric ring is constituted. The second prior art is to formulate a specific compound when manufacturing a contact lens, and there is no verification of hydrophilicity degradation performance due to harmful factors and specific compounds that a specific compound has on eye health.

Korean Patent Publication No. 10-2009-0036122 (2009.04.13.) Korean Patent No. 10-1786302 (2017.10.17.)

The technical problem to be achieved by the present invention is to provide a contact lens and a method for manufacturing the same, in which blue light that causes eye damage and fatigue is blocked due to high scattering properties and refractive index, and maintains original mechanical properties, and the contact lens is Provided are a blue light blocking contact lens using a tartrazine dye, which is made of a material having a blue light blocking effect and biocompatibility harmless to the human body, and the manufacturing process is simple, thereby reducing manufacturing time and cost, and a manufacturing method thereof.

In order to solve the above problems and achieve the object, a blue light blocking contact lens using a tartrazine dye according to an embodiment of the present invention is a hydrophilic monomer 2-hydroxyethylmethacrylate (HEMA, 2-Hydroxyethylmethacrylate) 60 to 95 wt%, hydrophilic monomer 2 to 39 wt%, blue light absorbing material tartrazine monomer 0.01 to 1 wt%, crosslinking agent 0.1 to 2 wt% and initiator azobisisobutyronitrile (AIBN, Azobisisobutyronitrile) 0.01 to 0.05 wt%.

The hydrophilic monomer is N-vinylpyrrolidone (NVP, N-vinyl pyrrolidone), N,N-dimethylacrylamide (DMAA, N,N-Dimethylacrylamide), methacrylic acid (methacrylic acid) and 2-methacryloyl At least one selected from among oxyethylphosphorylcholine (MPC, 2-methacryloyloxyethyl phosphorylcholine) is added.

The tartrazine monomer is sodium(E)-4-((5-hydroxy-3-((2-(methacryloyloxy)ethyl)carbamoyl)-1-(4-sulfonatophenyl)-1H-pyrazol-4-yl)diazenyl) benzenesulfonate (tartrazine monomer (1)) or sodium(E)-4-((5-hydroxy-3-((2-(methacryloyloxy)ethoxy)carbonyl)-1-(4-sulfonatophenyl)-1H-pyrazol-4 Use one selected from -yl)diazenyl)benzenesulfonate (tartrazine monomer (2)).

The cross-linking agent is ethylene glycol dimethacrylate (Ethylene glycol dimethacrylate), tetraethylene glycol dimethacrylate (Tetraethylene glycol dimethacrylate), trimethylol propane trimethacrylate (Trimethylolpropane trimethacrylate) of the monomers having a carbon double bond or more functional Provided is a blue light blocking contact lens using a tartrazine color flux using a mixture of one or more.

A method for manufacturing a contact lens that blocks blue light using a tartrazine dye is a) 60 to 95 wt% of a hydrophilic monomer 2-hydroxyethylmethacrylate (HEMA, 2-Hydroxyethylmethacrylate), 2 to 39 wt% of a hydrophilic monomer, and a blue light absorbing material A stirring step of mixing 0.01 to 1% by weight of tartrazine monomer, 0.1 to 2% by weight of a crosslinking agent, and 0.01 to 0.05% by weight of an initiator azobisisobutyronitrile (AIBN, Azobisisobutyronitrile), and stirring at room temperature for 1 hour; b) a mold injection step of injecting the mixture after the stirring step into the contact lens mold; and c) a polymerization step of polymerizing the mold in which the mixture is injected in a drying oven.

The polymerization step provides a method for manufacturing a blue light blocking contact lens using a tartrazine dye, which is polymerized at 80 to 130° C. for 1 to 6 hours in a drying oven.

As described above, the blue light blocking contact lens using the tartrazine dye and the manufacturing method thereof according to the present invention have the following effects.

(1) The present invention has a light transmittance of 90% or more in a region of 500 nm or more, and lowers the light transmittance in a blue light region of 500 nm or less while maintaining the original mechanical properties of a contact lens.

(2) The present invention realizes blue light blocking function and biocompatibility at the same time by using tartrazine, a food coloring, as a colorant.

(3) In the present invention, a methacrylate polymerization group is connected to the carboxyl functional group of tartrazine to copolymerize it with a material of a contact lens, and the manufacturing process is simple.

1 shows structural formulas (1) and (2) of a tartrazine monomer according to a preferred embodiment of the present invention.
2 is a process diagram of a method for manufacturing a blue light blocking contact lens using a tartrazine dye according to a preferred embodiment of the present invention.

The name of the present invention is "blue light blocking contact lens using tartrazine dye and manufacturing method thereof", so that a person skilled in the art can easily understand the specific content, and a separate description that can be sufficiently inferred is omitted, and if necessary, examples and The drawings are described. In addition, the terms defined in the present specification and claims are not limited to interpretation, may vary according to the intention or custom of the operator, etc., and should be interpreted as meanings and concepts consistent with the technical spirit of the present invention.

In one aspect of the present invention,

1 shows the structural formulas (1) and (2) of a tartrazine monomer according to a preferred embodiment of the present invention. With reference to FIG. 1, a blue light blocking contact lens using the tartrazine dye of the present invention is detailed below go ahead

In a contact lens that blocks blue light,

The contact lenses are

Hydrophilic monomer 2-hydroxymethacrylate (HEMA, 2-Hydroxyethylmethacrylate) 60 to 95 wt%, hydrophilic monomer 2 to 39 wt%, blue light absorbing material tartrazine monomer 0.01 to 1 wt%, crosslinking agent 0.1 to 2 wt% and initiator Azobisisobutyronitrile (AIBN, Azobisisobutyronitrile) consists of 0.01 ~ 0.05% by weight.

The tartrazine is food color yellow No. 4, a synthetic lemon azo dye used as a coloring agent, soluble in water, and has a water solubility of up to 327±2 nm, a color commonly used worldwide, and mainly yellowish.

The content of the tartrazine monomer is preferably 0.01 to 1% by weight in the total composition. The reason is that when it is used at less than 0.01% by weight, the transmission efficiency of blue light is insignificant, so that the use of tartrazine is practically meaningless, and when it is used in excess of 1% by weight, the yellow coloring of tartrazine becomes dark, making it difficult for the user to secure vision. , it is preferable to be within the above range because a third party may feel repulsive when seeing the user.

The hydrophilic monomer is N-vinylpyrrolidone (NVP, N-vinyl pyrrolidone), N,N-dimethylacrylamide (DMAA, N,N-Dimethylacrylamide), methacrylic acid (methacrylic acid) and 2-methacryloyl At least one selected from among oxyethylphosphorylcholine (MPC, 2-methacryloyloxyethyl phosphorylcholine) is added.

The tartrazine monomer is sodium(E)-4-((5-hydroxy-3-((2-(methacryloyloxy)ethyl)carbamoyl)-1-(4-sulfonatophenyl)-1H-pyrazol-4-yl)diazenyl) benzenesulfonate (tartrazine monomer (1)) or sodium(E)-4-((5-hydroxy-3-((2-(methacryloyloxy)ethoxy)carbonyl)-1-(4-sulfonatophenyl)-1H-pyrazol-4 Use one selected from -yl)diazenyl)benzenesulfonate (tartrazine monomer (2)).

The cross-linking agent is ethylene glycol dimethacrylate (Ethylene glycol dimethacrylate), tetraethylene glycol dimethacrylate (Tetraethylene glycol dimethacrylate), trimethylol propane trimethacrylate (Trimethylolpropane trimethacrylate) of the monomers having a carbon double bond or more functional Use a mixture of one or more.

In one aspect of the present invention,

FIG. 2 is a process diagram of a method for manufacturing a blue light blocking contact lens using a tartrazine dye according to a preferred embodiment of the present invention. Referring to FIG. 2, a method for manufacturing a blue light blocking contact lens will be described below.

In the method of manufacturing a contact lens that blocks blue light,

The contact lens manufacturing method is

a) 60 to 95 wt% of hydrophilic monomer 2-hydroxyethylmethacrylate (HEMA, 2-Hydroxyethylmethacrylate), 2 to 39 wt% of hydrophilic monomer, 0.01 to 1 wt% of blue light absorbing material tartrazine monomer, 0.1 to 2 wt% of crosslinking agent And a stirring step of mixing 0.01 to 0.05 wt% of an initiator azobisisobutyronitrile (AIBN, Azobisisobutyronitrile), and stirring at room temperature for 1 hour;

b) a mold injection step of injecting the mixture after the stirring step into the contact lens mold; and

c) a polymerization step of polymerizing the mold in which the mixture is injected in a drying oven;

The polymerization step is carried out in a drying oven at 80 ~ 130 ℃ polymerization for 1 ~ 6 hours.

Since the initiator azobisisobutyronitrile (AIBN, Azobisisobutyronitrile) is mainly used as an azo compound-based initiator, it may be used in the present invention, but may not be uniformly dissolved in the reaction solution. (BPO, Benzoyl peroxide) can be used instead.

Example : tatrazine monomer copolymerized hydrogel contact lens manufacturing

2-hydroxymethacrylate (HEMA) 70% by weight, N-vinylpyrrolidone 29% by weight, tartrazine monomer (1), ethylene glycol dimethacrylate 0.71 and 0.63% by weight, and azobisisobutyronitrile ( AIBN) 0.25 wt%, stirred at 20°C for 1 hour, injected into a contact lens mold, and polymerized for 3 hours at 100°C in a drying oven, but the content of the tartrazine monomer (1) was 0.04 A plurality of contact lenses were prepared by weight% and 0.12% by weight.

test example : tatrazine monomer copolymerized of contact lenses blue light Block rate measurement

A contact lens prepared by varying the content of the tartrazine monomer in the above example was used as a sample, and the blue light blocking rate was measured using a UV spectrometer (UV-1650PC spectrophotometer, Shimadzu), and the measurement was performed in a wavelength range of 300 to 700 nm at room temperature. was performed, and the average value was obtained by repeating measurements 4 times for each sample.

Table 1 below is the result of light transmittance in the visible light region when the content of the tartrazine monomer (1) is 0.04 wt%, and Table 2 is the light in the visible light region when the content of the tartrazine monomer (2) is 0.12 wt% It is the result of transmittance.

It was confirmed that blue light blocking was achieved in all contact lenses manufactured using tartrazine monomer (82% at 0.04% by weight, 68% at 0.12% by weight), and other light transmittances were high. The higher the content, the higher the blue light blocking rate. (The unit of the vertical axis is transmittance (%), the unit of the horizontal axis (nm))

In a further aspect,

The contact lens manufactured by the present invention can be hydrotreated, immersed in physiological saline containing sodium chloride, which is generally used, and then heat treated at 60 to 80° C. for 2 to 4 hours to remove unreacted monomers. Although it may be carried out by a method of removing it, a contact lens having a high moisture content can be manufactured by performing surface modification using sodium carboxymethyl cellulose (SCMC).

In order to manufacture the contact lens with high moisture content, after the polymerization step, a pretreatment step is performed with one selected from O2-plasma treatment, UV-O3 treatment and PVA, unreacted monomer and sterilization treatment, and a plurality of hydroxyl groups are introduced on the surface of the contact lens, A surface modification step is performed by introducing sodium carboxymethyl cellulose to the surface.

As described above, although the present invention has been described with reference to limited embodiments and drawings, the present invention is not limited thereto, and the technology to which the present invention belongs is within the scope of equivalents of the technical spirit of the invention and the claims to be described below. Of course, various modifications and variations are possible.

Claims (6)

In a contact lens that blocks blue light,
The contact lenses are
Hydrophilic monomer 2-hydroxymethacrylate (HEMA, 2-Hydroxyethylmethacrylate) 60 to 95 wt%, N-vinylpyrrolidone (NVP, N-vinyl pyrrolidone), N,N-dimethylacrylamide (DMAA, N,N -Dimethylacrylamide), methacrylic acid, and 2-methacryloyloxyethyl phosphorylcholine (MPC, 2-methacryloyloxyethyl phosphorylcholine) at least one hydrophilic monomer selected from 2 to 39% by weight, blue light absorbing material tartrazine monomer 0.01 ~ 1% by weight, 0.1 ~ 2% by weight of a crosslinking agent, and 0.01 ~ 0.05% by weight of the initiator azobisisobutyronitrile (AIBN, Azobisisobutyronitrile),
The tartrazine monomer is sodium(E)-4-((5-hydroxy-3-((2-(methacryloyloxy)ethyl)carbamoyl)-1-(4-sulfonatophenyl)-1H-pyrazol-4-yl)diazenyl) benzenesulfonate (tartrazine monomer (1)) or sodium(E)-4-((5-hydroxy-3-((2-(methacryloyloxy)ethoxy)carbonyl)-1-(4-sulfonatophenyl)-1H-pyrazol-4 -yl)diazenyl)benzenesulfonate (tartrazine monomer (2)) blue light blocking contact lens using a tartrazine dye, characterized in that it uses one. delete delete According to claim 1,
The crosslinking agent is ethylene glycol dimethacrylate (Ethylene glycol dimethacrylate), tetraethylene glycol dimethacrylate (Tetraethylene glycol dimethacrylate), trimethylolpropane trimethacrylate (Trimethylolpropane trimethacrylate) of the monomers having a carbon double bond or more functional Blue light blocking contact lenses using a tartrazine pigment, characterized in that one or more are mixed and used. In the method for manufacturing a blue light blocking contact lens using the tartrazine dye of claim 1,
The contact lens manufacturing method is
a) Hydrophilic monomer 2-hydroxymethacrylate (HEMA, 2-Hydroxyethylmethacrylate) 60 to 95 wt%, N-vinylpyrrolidone (NVP, N-vinyl pyrrolidone), N,N-dimethylacrylamide (DMAA, N ,N-Dimethylacrylamide), methacrylic acid and 2-methacryloyloxyethyl phosphorylcholine (MPC, 2-methacryloyloxyethyl phosphorylcholine) at least one hydrophilic monomer selected from 2 to 39 wt%, sodium (E)- 4-((5-hydroxy-3-((2-(methacryloyloxy)ethyl)carbamoyl)-1-(4-sulfonatophenyl)-1H-pyrazol-4-yl)diazenyl)benzenesulfonate (tartrazine monomer (1)) or sodium(E)-4-((5-hydroxy-3-((2-(methacryloyloxy)ethoxy)carbonyl)-1-(4-sulfonatophenyl)-1H-pyrazol-4-yl)diazenyl)benzenesulfonate (tartrazine monomer (2)) 0.01 to 1% by weight of the blue light absorbing material tartrazine monomer, 0.1 to 2% by weight of a crosslinking agent, and 0.01 to 0.05% by weight of an initiator azobisisobutyronitrile (AIBN, Azobisisobutyronitrile) are mixed, A stirring step of stirring for 1 hour in;
b) a mold injection step of injecting the mixture after the stirring step into the contact lens mold; and
c) a polymerization step of polymerizing the mold in which the mixture is injected in a drying oven;
The polymerization step is a blue light blocking contact lens manufacturing method using a tartrazine dye, characterized in that the polymerization is carried out at 80 ~ 130 ℃ for 1 ~ 6 hours in a drying oven. delete

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