KR102654801B1 - Blue light blocking hydrogel contact lens composition and hydrogel contact lens comprising the same - Google Patents

Abstract

The present invention relates to an ophthalmic device composition containing a material capable of blocking blue light and an ophthalmic device manufactured using the same.

Description

Blue light blocking hydrogel contact lens composition and hydrogel contact lens comprising the same {Blue light blocking hydrogel contact lens composition and hydrogel contact lens comprising the same}

The present invention relates to a blue light blocking ophthalmic device composition and an ophthalmic device comprising the same. Specifically, it relates to a hydrogel contact lens composition containing a material capable of blocking blue light and a hydrogel contact lens manufactured using the same.

The light that we can easily access consists of visible light, ultraviolet rays, and infrared rays. The wavelength of visible light is 380 to 780 nm, shorter wavelengths are called ultraviolet rays, and longer wavelengths are called infrared rays. Visible light and infrared light, including red, yellow, and green light, with long wavelengths, are less harmful, but ultraviolet rays with shorter wavelengths are highly irritating to the skin and eyes. Various methods to block these ultraviolet rays, such as sunblock cream and sunglasses, are already being used on a daily basis around us.

The harmfulness of blue light, which has a short wavelength among visible light, and methods for blocking it have been known in recent years, and much research is still needed for commercialization (see Non-Patent Documents 1 to 4). Blue light refers to the wavelength range of 400 to 500 nm, and has a short wavelength, high scattering properties, and a high refractive index. Due to these characteristics, blue light reduces the quality of images formed on the retina, forms images in front of the retina, and causes chromatic aberration, causing eye fatigue and glare.

In particular, blue light in the 400 to 450 nm region has high energy and causes adverse effects on visual cells (see Non-Patent Document 5). According to Non-Patent Document 5, the retina is the only part of the central nervous system that is exposed to light between 400 and 780 nm, and short wavelength light (SWL) in the range of 400 to 480 nm is maximized by chromophores located in mitochondria. is absorbed into Mitochondria are located in retinal ganglion cell (RGC) guide axons and photoreceptor inner segments, and consequently, short-wavelength light affects these organelles. For empirical evidence, we performed exposure of short-wavelength light to the mitochondria of retinal ganglion cells, and the results indicated that short-wavelength light contributes to RGC death, similar to conditions such as glaucoma and other types of pathology and even old age. For this reason, there is a need to shield RGCs to slow vision loss in certain situations. A lens is needed that reduces the transmission of short-wavelength light while allowing maximum transmission of 479 nm light to stimulate melanopsin and maintain an optimal sleep/wake cycle.

Exposure to an appropriate amount of blue light included in natural light during the day triggers beneficial physiological effects such as circadian rhythm synchronization, pupil constriction, and fatigue reduction. Displays such as smartphones, tablets, computers, TVs, etc. contain a much higher proportion of blue light than sunlight or fluorescent lights, which can cause blurred vision, glare, fatigue, headaches, etc. (see Non-Patent Documents 6 to 8).

Although research on spectacle lenses or protective films for blocking blue light is being actively conducted (see Non-Patent Documents 9 to 10), research on contact lenses for blocking blue light is still insufficient.

Conventional spectacle lenses or protective films that block blue light 1) absorb blue light by adding a brown or orange dye as a colorant, or 2) alternately coat a material with a high and low refractive index to block the area corresponding to blue light. The wavelength was reflected. It is known to be difficult to apply this conventional technology to hydrogel contact lenses. When blue light-absorbing dyes or blue light-blocking materials are used in contact lenses, 1) the overall transmittance of not only blue light but also visible light may decrease, which may reduce visibility. 2) Due to a problem with the chemical bond between the dye and the contact lens, the dye may escape from the contact lens and cause serious damage to the eyes (see Patent Document 1).

The blue light blocking material must be covalently bound to the polymer network of the contact lens material instead of simply being physically captured within the contact lens material to prevent the material from migrating, phase separating, or leaching from the contact lens material. This characteristic is particularly important in contact lenses, as leaching of blue light blocking substances can present toxicological issues.

Conventionally, in addition to brown or orange dyes, ultraviolet absorbers are sometimes used, but these do not meet the purpose of the present invention because they block ultraviolet rays (400 nm or less).

Spectacle lenses containing ultraviolet absorbers are disclosed in U.S. Pat. No. 5,290,892; No. 5,331,073; and 5,693,095. In addition to blocking UV rays, some eyeglass lenses also block blue light. This is described, for example, in U.S. Patent Nos. 5,470,932 and 5,543,504. These lenses block two types of light by using two chromophores: an ultraviolet absorber and a yellow dye.

Republic of Korea Patent Publication No. 1786302 (2017.10.10) (Patent Document 1)

Fletcher AE, Bentham GC et al.: Sunlight exposure, antioxidants, and age-related macular degeneration. Arch Ophthalmol. 126(10), 1396-1403, 2008. DOI: https://doi.org/10.1001/archopht.126.10.1396 Yu YG, Choi EJ: Blue Light Blocking Performance and Prescription for Blue Light Blocking Lenses. J Korean Oph Opt Soc. 18(3), 297-304, 2013. DOI: http://dx.doi.org/10.14479/jkoos.2013.18.3.297 Lee JY, Yun EJ et al.: The changes of the eye and a correction depending on watching a smartphone and taking in alcohol. J Korean Oph Opt Soc. 18(4), 473-479, 2013. DOI: https://doi.org/10.14479/jkoos.2013.18.4.473 Kim BH, Han SH et al.: Aided distance visual acuity and refractive error changes by using smartphone. J Korean Oph Opt Soc. 17(3), 305-309, 2012. http://www.riss.kr/link?id=A103824130 Osborne NN, Nunez-Alvarez C et al.: The effect of visual blue light on mitochondrial function associated with retinal ganglions cells. Exp Eye Res. 128, 8-14, 2014. DOI: https://doi.org/10.1016/j.exer.2014.08.012 Johar SR, Rawal UM et al.: Sequential effects of ultraviolet radiation on the histomorphology, cell density and antioxidative status of the lens equation an in vivo study. Phtochem Photobiol. 78(3), 306-311, 2003. DOI: https://doi.org/10.1562/0031-8655(2003)0780306SEOURO2.0.CO2 Biteau J, Chaput F et al.: Large and Stable Refractive Index Change in Photochromic Hybrid Materials. Chem Master. 10(7), 1945-1950, 1998. DOI: https://doi.org/10.1021/cm980106h Jung MH, Yang SJ et al.: Evaluation of blue light hazards in LED lightings. J Korean Oph Opt Soc. 20(3), 293-300, 2015. DOI: https://doi.org/10.14479/jkoos.2015.20.3.293 Kim CJ, Choi SW et al.: Evaluation of Bluelight Blocking Ratio and Luminous Transmittance of Blue-light Blocking Lens based on International Standard. J Korean Oph Opt Soc. 19(2), 135-143, 2014 DOI: http://dx.doi.org/10.14479/jkoos.2014.19.2.135 Park SJ, Yang HK et al.: Ultraviolet to blue blocking and wavelength convertible films using carbon dots for interrupting eye damage caused by general lighting. Nano Energy 60, 87-94, 2019. DOI: https://doi.org/10.1016/j.nanoen.2019.03.043 ANSI Z80.20 OPHTHALMICS CONTACT LENSES STANDARD TERMINOLOGY, TOLERANCES, MEASUREMENTS AND PHYSICOCHEMICAL PROPERTIES, 2016.

The present invention is intended to solve the above problems, and includes: 1) a composition for hydrogel contact lenses that can block blue light without reducing the overall transmittance of visible light and 2) without dye leakage problems, and a hydrogel contact containing the same. The purpose is to provide a lens.

In order to achieve the above object, the present invention provides an ophthalmic device composition containing a blue light blocking compound of the following formula (1).

(One)

Here, R ₁ is at least one of C ₁ to C ₁₂ alkylene, (CH ₂ CH ₂ O) _n , (CH ₂ CH(CH ₃ )O) _n , and C(=O);

X is a simple connection that does not exist when r ₁ is c ₁ to ₁₂ alkylene or c (= o), and r ₁ is (ch ₂ ch ₂ o) _n or (ch ₂ ch (ch ₃ ) o) _n If it is C ₁ to C ₁₂ alkylene or C(=O);

R ₂ is one of H, OH, C ₁ to C ₆ alkyl or phenyl;

R ₃ is one of H, OH, C ₁ to C ₆ alkyl or phenyl,

n is an integer from 1 to 12.

Preferably,

R ₁ is at least one of C ₁ to C ₁₂ alkylene, (CH ₂ CH ₂ O) _n , (CH ₂ CH(CH ₃ )O) _n , and C(=O),

_X does not exist when R ₁ is C ₁ to C ₁₂ alkylene or C(=O), and when R ₁ is (CH ₂ CH ₂ O) _n or (CH ₂ CH(CH ₃ )O) _n, to C ₁₂ alkylene or C(=O),

R ₂ is one of H, CH ₃ , OH,

R ₃ is one of H, OH, C ₁ to C ₆ alkyl, phenyl,

n is an integer from 1 to 12.

More preferably,

R ₁ is C ₁ to C ₁₂ alkylene,

X is a simple connection,

R ₂ and R ₃ are each one of H, CH ₃ and OH.

Most preferably,

R ₁ is C ₁ to C ₁₂ alkylene,

X is a simple connection,

R ₂ and R ₃ are each H.

The present invention also provides an ophthalmic device composition comprising a blue light blocking compound of formula (IV):

(IV)

The ophthalmic device may include an intraocular lens; contact lenses; artificial cornea (keratoprosthesis); and a corneal inlay or ring.

The ophthalmic device composition according to the present invention may further comprise a device-forming monomer selected from the group comprising acrylic monomers and silicone-containing monomers.

The group containing the acrylic monomer and silicone-containing monomer includes HEMA (2-Hydroxyethyl methacrylate) and EGDMA (ethylene glycol dimethacrylate).

The blue light blocking compound of Formula 1 may be contained in an amount of 0.05% to 5% by weight, preferably 0.1% to 2% by weight, and most preferably 0.5% to 2% by weight of the total composition.

The present invention also provides an ophthalmic device manufactured by the ophthalmic device composition, wherein the moisture content of the ophthalmic device is 30 to 70% by weight, preferably 30 to 50% by weight, more preferably 30 to 45% by weight. %am.

The ophthalmic device according to the present invention comprises a reactive blue light absorbing compound.

The present invention can also be provided by combining the above solutions in any of various ways.

The blue light blocking hydrogel contact lens according to the present invention maintains visible light transmittance and is excellent in blocking ultraviolet rays and especially blocking light with a wavelength of 400 to 450 nm, which is known to have a negative effect on the retina among blue light. In addition, the moisture content, which is important for the wearing comfort of contact lenses, was found to be equivalent to that of commercially available products, allowing it to prevent glare and fatigue caused by ultraviolet rays and blue light while maintaining the physical properties that existing contact lenses should have.

Figure 1 shows the visible light and ultraviolet ray absorption rate results for Examples 1 to 5 and Comparative Examples 1 and 2.
Figure 2 is an NMR spectrum for the blue light blocking compound (IV) according to the present invention.
Figure 3 is Scheme 1 showing the synthesis process of benzotriazole according to the present invention.

Hereinafter, with reference to the attached drawings, an embodiment in which the present invention can be easily implemented by those skilled in the art will be described in detail. However, when explaining in detail the operating principle of a preferred embodiment of the present invention, if it is determined that a detailed description of a related known function or configuration may unnecessarily obscure the gist of the present invention, the detailed description will be omitted.

In addition, the same reference numerals are used for parts that perform similar functions and actions throughout the drawings. Throughout the specification, when a part is said to be connected to another part, this includes not only cases where it is directly connected, but also cases where it is indirectly connected through another element in between. Additionally, including a certain component does not mean excluding other components unless specifically stated to the contrary, but rather means that other components may be further included.

In addition, limitations or additions to an embodiment in this specification not only apply to a specific embodiment, but may also be equally applied to other embodiments.

The blue light blocking compound according to the present invention has the structure of Formula 1 below:

(One)

Here, R ₁ is at least one of C ₁ to C ₁₂ alkylene, (CH ₂ CH ₂ O) _n , (CH ₂ CH(CH ₃ )O) _n , and C(=O);

X is a simple connection that does not exist when r ₁ is c ₁ to ₁₂ alkylene or c (= o), and r ₁ is (ch ₂ ch ₂ o) _n or (ch ₂ ch (ch ₃ ) o) _n If it is C ₁ to C ₁₂ alkylene or C(=O);

R ₂ is one of H, OH, C ₁ to C ₆ alkyl or phenyl;

R ₃ is one of H, OH, C ₁ to C ₆ alkyl or phenyl,

n is an integer from 1 to 12.

Preferably,

R ₁ is at least one of C ₁ to C ₁₂ alkylene, (CH ₂ CH ₂ O) _n , (CH ₂ CH(CH ₃ )O) _n , and C(=O),

_X does not exist when R ₁ is C ₁ to C ₁₂ alkylene or C(=O), and when R ₁ is (CH ₂ CH ₂ O) _n or (CH ₂ CH(CH ₃ )O) _n, to C ₁₂ alkylene or C(=O),

R ₂ is one of H, CH ₃ , OH,

R ₃ is one of H, OH, C ₁ to C ₆ alkyl, phenyl,

n is an integer from 1 to 12.

More preferably,

R ₁ is C ₁ to C ₁₂ alkylene,

X is a simple connection,

R ₂ and R ₃ are each one of H, CH ₃ and OH.

The blue light blocking compound according to an embodiment of the present invention has the structure of Formula IV below.

(IV)

The compound of formula IV is 2-[2'-hydroxy-3'-tert-butyl-5'-allyloxy]-5-methoxy-2H-benzotriazole.

<Production method of Formula 1>

Compounds of Formula 1 can be prepared using methods known in the art (see U.S. Patent No. 7,825,257). For example, Chemical Formula IV according to an embodiment of the present invention can be synthesized using the synthetic route shown in Scheme 1 below. The route starts with methoxy-substituted 2-nitroaniline, which is converted to a diazonium salt and azocoupled with 2-tert-butyl-4-(3'-benzyloxy)phenol, followed by glucose and zinc powder. Reduction of the nitro azo intermediate (I) is performed and the benzotriazole ring is cyclized to provide the desired methoxy-substituted benzotriazole compound (II). In the final synthesis steps, polymerizable groups, such as allyl groups, can be incorporated by methods known in the art. Other methoxy-substituted benzotriazole compounds of formula (IV) can also be prepared using this same synthetic route.

Figure 3 is Scheme 1 showing the synthesis process of benzotriazole according to the present invention.

The blue light blocking compounds according to the present invention are particularly suitable for use in contact lenses. The composition for contact lenses may contain 0.05% to 5% by weight of the compound according to formula (I), preferably 0.1% to 2% by weight, and most preferably 0.5% to 2% by weight.

Ophthalmic device materials can be prepared by copolymerizing the blue light blocking compounds according to the present invention with other ingredients, such as device-forming materials, crosslinkers, and blue light blocking chromophores.

Many ophthalmic device-forming monomers are known in the art, including acrylic and silicone-containing monomers. Specific information in this regard is US Patent No. 7,101,949; No. 7,067,602; No. 7,037,954; No. 6,872,793; No. 6,852,793; No. 6,846,897; No. 6,806,337; No. 6,528,602; and 5,693,095, so detailed description thereof will be omitted. For contact lenses, any known contact lens device material is suitable for use in the compositions of the present invention. Ophthalmic device materials suitable for the present invention include acrylic or methacrylic device-forming monomers.

The blue light blocking compounds according to the invention are suitable for use in ophthalmic devices, such as contact lenses, keratoprosthesis, and corneal inlays or rings. The invention will be further illustrated by the following examples, which are intended to be illustrative but not limiting.

<Preparation Example 1. Synthesis of blue light blocking compound>

Synthesis of 2-[2'-hydroxy-3'-tert-butyl-5'-allyloxy]-5-methoxy-2H-benzotriazole

The following synthetic reaction follows the synthesis process of benzotriazole (Scheme 1), and the resulting intermediate products are also indicated as (I), (II), (III), and (IV).

i) 20 ml of distilled water and 5.85 ml of hydrochloric acid were added to the round bottom flask, and 4-methoxy-2-nitroaniline (3.325 g, 19.77 mmol) was slowly added. The reaction mixture was stirred for 15 minutes and then cooled again. NaNO ₂ aqueous solution (1.4 g, 20.3 mmol dissolved in 4.2 ml of distilled water) was added to the round bottom flask and stirred for 45 minutes. Afterwards, the insoluble suspended solids were filtered through celite to obtain an aqueous solution in which 4-methoxy-2-nitrobenzenediazonium chloride was dissolved.

ii) Add 4-(benzyloxy)-2-(tert-butyl)phenol (3.12 g, 12.17 mmol) to a separate 50 mL round bottom flask, then add 36 mL of ethanol to dissolve it, and add KOH aqueous solution (2.65 g, 47.23 mmol dissolved in 11.62 ml of distilled water) was added for 5 minutes. The temperature of the reaction mixture was cooled to -25°C, and the aqueous 4-methoxy-2-nitrobenzenediazonium chloride solution obtained in step i) was added for 10 minutes, followed by adding a KOH aqueous solution (1.97 g, 35.11 mmol) in distilled water at 11.62 °C. (dissolved in mL) was added for 5 minutes. When the addition was completed, the temperature of the reaction mixture was -20°C. After 30 minutes while maintaining the temperature, the brown solid produced inside the reactor was filtered, and the filtered solid was placed in a separate flask containing 10 ml of methanol and stirred for 5 minutes. The solid was filtered again and dried under vacuum for more than 6 hours to obtain 4-(benzyloxy)-2-(tert-butyl)-6-((4-methoxy-2-nitrophenyl)diazenyl)phenol(I) ( 5.3g, 100%) was obtained.

iii) 3.12 g of the 4-(benzyloxy)-2-(tert-butyl)-6-((4-methoxy-2-nitrophenyl)diazenyl)phenol(I) in a nitrogen atmosphere in a round bottom flask, 7.165 mmol) and 36 ml of anhydrous ethanol were added, and an aqueous glucose solution (2.496 g, 13.85 mmol dissolved in 15.6 ml of 2N NaOH aqueous solution) was added for 5 minutes. The reaction mixture was stirred at room temperature for 58 hours, at which time a yellow solid was produced. Zn powder (5.46 g, 83.5 mmol) was slowly added here for 5 minutes. The temperature of the reaction mixture was raised to 60°C and stirred for 6 hours. Afterwards, the temperature of the reaction mixture was cooled to room temperature, and 15 ml of hexane/toluene (2/1) (volume ratio) was added and extracted. 15 mL of new hexane/toluene (2/1) (volume ratio) was added to the remaining reaction mixture (unextracted liquid), and extraction was repeated twice. The extracted organic layer was collected and concentrated, and 5 ml of hexane/toluene (95/5) (2/1) (volume ratio) solution was added to the concentrated residue, stirred for 30 minutes, and the undissolved solid was obtained by filtration. 3 ml of methanol was added to the solid and stirred, and after stirring for 30 minutes, the undissolved solid was filtered and dried in vacuum for more than 6 hours to obtain 4-(benzyloxy)-2-(tert-butyl)-6-(5-meth. Toxy-2H-benzo[d][1,2,3]triazol-2-yl)phenol(II) (1.34g 3.32mmol 46.3%) was obtained.

iv) The above 4-(benzyloxy)-2-(tert-butyl)-6-(5-methoxy-2H-benzo[d][1,2,3]triazole-2 was added to the round bottom flask under nitrogen atmosphere. -1) Phenol (II) (3.10 g, 7.68 mmol) was added and dissolved in 52 ml of anhydrous ethanol. Next, 0.3 g of 10% Pd/C (weight ratio) and 0.75 mL of distilled water from which dissolved oxygen was removed were added, followed by formic acid (1.16 g, 25.2 mmol) and ammonium formic acid aqueous solution (1.45 g, 23 mmol dissolved in 0.76 mL of distilled water). After adding the mixture, the temperature of the reaction mixture was raised to 50°C and stirred for 6 hours. The temperature of the reaction mixture was lowered to room temperature, and the resulting suspended solids were removed by filtration. The filtered filtrate was diluted in 31 ml of distilled water and extracted using 60 ml of toluene. The toluene layer was washed with 30 ml of ethanol/distilled water (1/1) (volume ratio). The toluene layer was dried with anhydrous sodium sulfate, and about 80% of the toluene was concentrated and removed, cooled, and the resulting solid was filtered and washed with 1 ml of methanol. The washed solid was dried under vacuum for more than 6 hours to form 2-(tert-butyl)-6-(5-methoxy-2H-benzo[d][1,2,3]triazol-2-yl)benzene- 1,4-diol(III) (1.25 g, 4 mmol 52%, purity 98%) was obtained.

v) 2-(tert-butyl)-6-(5-methoxy-2H-benzo[d][1,2,3]triazol-2-yl)benzene-1,4 in a 20 mL round bottom flask. -Diol(III) (1 g, 3.20 mmol) was added, followed by sequentially adding 10 ml of anhydrous ethanol, allyl bromide (1 g, 8.3 mmol), and 2.56 g of 10% NaOH aqueous solution, and stirring at room temperature for 10 hours. The resulting solid was filtered and washed with 10 ml of distilled water and 10 ml of ethanol. The washed solid was dried in vacuum for more than 10 hours to produce 2-[2'-hydroxy-3'-tert-butyl-5'-allyloxy]-5-methoxy-2H-benzotriazole(IV) (hereinafter ' BL') (0.46 g, 1.3 mmol, 40.6%) was obtained.

The obtained compounds were confirmed through NMR. Figure 2 is an NMR spectrum for the blue light blocking compound (IV) according to the present invention. Allyl ether (5.34-6.11 ppm) was identified in the NMR spectrum. ¹ HNMR data was measured using a Bruker AC-250 MHz spectrometer, and d6-DMSO (Dimethyl Sulfoxide) and CDCl ₃ were used as ¹ H-NMR solvents. Each peak is as follows. δ: 11.53(s, 1H) 7.81(d, 1H), 7.77(s, 1H), 7.17(s, 1H), 7.12(d, 1H), 7.03(s, 1H) 6.11(dd, 1H, C= CH-), 5.51(d, 1H, H2C=C), 5.34(dd, 1H, H2C=C), 4.60(dd, 2H, O-CH ₂ ), 3.93(s, 3H, O-CH ₃ ), 1.49(s, 9H, t-Bu)

<Manufacturing Example 2. Manufacturing of blue light blocking contact lenses>

A blue light blocking contact lens was manufactured using a cast mold method in which the blue light blocking compound according to the present invention and the contact lens monomer were copolymerized in a mold.

BL according to the present invention was added to HEMA (2-Hydroxyethyl methacrylate, 2-hydroxyethyl methacrylate) and EGDMA (ethylene glycol dimethacrylate), and AIBN (azobis) was used as a radical initiator. isobutyronitrile (Azobis isobutyronitrile) was used. The mixed monomers were heat-polymerized in an oven (95°C, 6 hours) using a cast mold method to produce contact lenses. Afterwards, it was soaked in distilled water for 3 days to remove unreacted impurities. The manufactured contact lenses were hydrated in physiological saline solution (0.9% by weight) for 24 hours and then their physical properties were measured. The contact lenses were named Example 1 (BLC1) to Example 5 (BLC5) according to the concentration (% by weight) of the sample used in the experiment. The ratios of monomers used in Examples 1 to 5 are shown in Table 1. In Table 1, Ref.-HL is a contact lens manufactured in the same manner as the Example except that BL is not used as a comparative example. Comparative Example 2 is a commercially available blue light blocking hydrogel contact lens from I Company (hereinafter referred to as I-lens).

<Performance evaluation of contact lenses>

¹ HNMR data was measured using a Bruker AC-250 MHz spectrometer, and d6-DMSO (Dimethyl Sulfoxide) and CDCl ₃ were used as ¹ H-NMR solvents. GENOVA NANO (Bibby Scientific, UK) was used for light transmittance. Moisture content was measured using the gravimetric method.

1) Light transmittance

To evaluate the optical performance of the manufactured contact lenses, light transmittance was measured. The average transmittance T(λ ₁ , λ ₂ ) from a specific wavelength λ ₁ to λ ₂ was calculated using Equation 1 below. τ(λ) is the spectral distribution, and S(λ) is the spectral distribution of the incident light.

Equation 1

2) Blocking rate

The average transmittance from specific wavelength λ ₁ to λ ₂ was calculated using Equation 2 below.

Equation 2

3) Moisture content

The weight of the contact lens with surface moisture removed was measured, and then the hydrated contact lens was dried in a dryer at 40°C for 48 hours and its weight was measured. The moisture content of the contact lens was calculated using Equation 3 below.

Equation 3

Here, m _hydrated and m _dry refer to the weight of hydrated and dry contact lenses, respectively.

<Comparison of Examples 1 to 5 and Comparative Examples 1 and 2>

The comparative results for optical properties are shown in Table 2 and Figure 1. Table 2 shows the light transmittance for each light, and Figure 1 shows the visible light and ultraviolet ray absorption rates for Examples 1 to 5 and Comparative Examples 1 and 2 with respect to wavelength.

To check the optical properties of contact lenses, the light transmittance is classified into visible light (380㎚ to 780㎚), blue light (400㎚ to 450㎚), UVA (380㎚ to 420㎚), and UVB (320㎚ to 380㎚). Measured.

<Visual light light transmittance>

As a result of analyzing the light transmittance, Examples 1 to 5 all showed a light transmittance of more than 90% in the visible light region, meeting the ANSI Z80.20 standard (88% or more based on transparent lenses) (see Non-patent Document 11) and meeting the regulations. It was found to be suitable.

From Example 1 to Example 5, the proportion of blue light blocking compounds increases. Example 5 showed the lowest visible light transmittance of 93.39ㅁ5.66. This appears to lower the overall light transmittance of visible light because the blocking rate of blue light included in the range of visible light increases.

It can be seen that Examples 1 to 5 all have higher visible light transmittance compared to a commercially available I-lens (Comparative Example 2). Example 1 showed visible light transmittance similar to Comparative Example 1.

<Blue light blocking rate>

The results for blue light blocking rate are listed in Table 3.

Among the structures of the blue light blocking compound (BL) used to manufacture blue light blocking contact lenses, it has a methoxy group at position 5 of the benzotriazole ring, so it can block harmful rays from the ultraviolet rays to the blue light range.

As a result of checking the blue light blocking performance with a wavelength of 400 to 450 nm, it was confirmed that the higher the ratio of blue light blocking compound (BL), the higher the blue light blocking rate. In Korea, standards for the range of blue light and the blue light blocking performance of contact lenses have not been established, making objective performance evaluation difficult. However, when more than 0.2% by weight of blue light blocking compound was used (Examples 3 to 5), commercially available It can be seen that the blue light blocking performance (400 to 450 nm, 400 to 500 nm) is superior to Comparative Example 2. Detailed experiments on blue light are listed in Table 3.

<Ultraviolet rays (UVA, UVB) blocking rate>

The results for UV protection rate are listed in Table 4.

In the case of UV blocking performance, in Examples 3 to 5 when 0.2% or more of blue light blocking compound (BL) was used, the blocking performance was 46% to 77% for UVA and 68% to 95% for UVB. It was confirmed that the UV blocking performance was superior to that of Comparative Example 2. In particular, the blocking performance against UVA (380 to 420 nm), which is known to be more harmful than blue light, is significantly higher than that of Comparative Example 2, showing that it is very effective in blocking harmful rays.

<Moisture content>

The results for moisture content are listed in Table 5.

As a result of measuring the moisture content, the moisture content of Comparative Example 2 was found to be about 40.5%, and the moisture content of Examples 1 to 5 was found to be 40.5% to 39.4.%. The reason that Examples 1 to 5 and Comparative Example 2 showed similar results is believed to be because the amount of blue light blocking compound (BL) was small and did not significantly affect the moisture content. In addition, in the structure of the blue light blocking compound used to manufacture contact lenses, there is a hydroxyl group at position 4 of phenol, which appears to be advantageous in maintaining moisture content. Examples 1 to 5 according to the present invention demonstrated that it is possible to manufacture contact lenses with excellent UV and blue light blocking performance without affecting the wearing comfort of existing contact lenses.

Anyone skilled in the art to which the present invention pertains will be able to perform various applications and modifications within the scope of the present invention based on the above contents.

Claims (11)

In the ophthalmic device composition comprising a blue light blocking compound of formula 1 below,
further comprising a device-forming monomer selected from the group comprising acrylic monomers and silicone-containing monomers,
The group containing the acrylic monomer and silicone-containing monomer includes ophthalmic device compositions including HEMA (2-Hydroxyethyl methacrylate) and EGDMA (ethylene glycol dimethacrylate) ,
(One)
Here, R ₁ is at least one of C ₁ to C ₁₂ alkylene, (CH ₂ CH ₂ O) _n , (CH ₂ CH(CH ₃ )O) _n , and C(=O);
X is a simple connection that does not exist when r ₁ is c ₁ to ₁₂ alkylene or c (= o), and r ₁ is (ch ₂ ch ₂ o) _n or (ch ₂ ch (ch ₃ ) o) _n If it is C ₁ to C ₁₂ alkylene or C(=O);
R ₂ is one of H, OH, C ₁ to C ₆ alkyl or phenyl;
R ₃ is one of H, OH, C ₁ to C ₆ alkyl or phenyl,
n is an integer from 1 to 12. According to paragraph 1,
R ₂ is one of H, CH ₃ and OH in the ophthalmic device composition. According to paragraph 1,
R ₁ is C ₁ to C ₁₂ alkylene,
X is a simple connection,
R ₂ and R ₃ are each one of H, CH ₃ , and an ophthalmic device composition. An ophthalmic device composition comprising a blue light blocking compound of formula IV below,
(IV) According to paragraph 1,
The ophthalmic device may include an intraocular lens; contact lenses; artificial cornea (keratoprosthesis); and an ophthalmic device composition that is one of a corneal inlay or ring. delete delete According to paragraph 1,
An ophthalmic device composition in which the blue light blocking compound of Formula 1 accounts for 0.05% to 5% by weight of the total composition. delete An ophthalmic device manufactured by the ophthalmic device composition according to any one of claims 1 to 5 and 8. According to clause 10,
The ophthalmic device has a moisture content of 30 to 70% by weight.