KR20190023448A - Compositions for hydrogel contact lens having high performance - Google Patents

Abstract

The present invention relates to a high functional hydrogel contact lens composition, which can manufacture a high functional silicon hydrogel contact lens to which a material having various functionalities can be added, and having a drug delivery function, by using SiONO_2 which is a silicon monomer obtained by bonding an acryl group to an SiONH_2 reagent prepared by using N,N-dimethylacrylamide (DMA) and an SiNH_2 reagent to synthesize the same. According to the present invention, the high functional hydrogel contact lens composition is mixed with SiONO_2 which is a silicon monomer obtained by bonding an acryl group to an SiONH_2 reagent prepared by using DMA and an SiNH_2 reagent to synthesize the same.

Description

≪ Desc / Clms Page number 1 > COMPOSITIONS FOR HYDROGEL CONTACT LENS HAVING HIGH PERFORMANCE &

The present invention relates to a high-performance hydrogel contact lens composition, and more particularly to a SiONH ₂ reagent prepared by using DMA (N, N-dimethylacrylamide, N, N-dimethyl acrylamide) and SiNH ₂ reagent, Functional hydrogel lens composition capable of producing a highly functional silicone hydrogel contact lens capable of adding a material having various functionalities and having a drug delivery function by using SiONO ₂ synthesized as a silicone monomer.

 An ophthalmic lens is required to secure oxygen permeability, antibacterial and wettability to compensate for wearing comfort and ophthalmic diseases when worn.

Various studies using additives such as butanediol and glycerin have been actively carried out to increase the wettability of the lens. As one method for increasing the oxygen permeability (Dk), there has been used a silicone synthetic monomer Research on silicone hydrogel lenses is actively under way. Korean Patent Registration No. 10-0250192 (Method of producing hydrogel lens containing silicon), Korean Patent Laid-open Publication No. 10-2017-0097573 (siloxane monomer, composition for producing silicone hydrogel lens containing same and silicone hydrogel lens) And Korean Patent Registration No. 10-1231181 (silicone hydrogel compositions for soft contact lenses and soft contact lenses produced by the composition) disclose techniques for producing high-performance hydrogel lenses using silicon.

In addition, Korean Patent No. 10-1553685 (antibacterial hydrogel contact lens and manufacturing method thereof) and Korean Patent No. 10-1545757 (hydrogel contact lens manufacturing method) disclose a method for securing the antibacterial property of a hydrogel lens Technology is disclosed.

Despite the various attempts described above, studies on high-performance hydrogel contact lenses that can provide high functionality through the addition of various materials and sufficiently demonstrate their functionality through effective drug delivery of the added drug are somewhat lacking.

On the other hand, DMA-based polymers are attracting much attention because they are suitable for various practical applications such as drug delivery, polypeptide synthesis, polymer support for coagulant and catalytic reaction, and DMA has high polarity and high solubility, It can be applied to various organic solvents and is used in various fields.

Korean Patent Registration No. 10-0250192: Method for producing hydrogel lens containing silicon Korean Patent Laid-Open Publication No. 10-2017-0097573: Siloxane monomers, compositions for the production of silicone hydrogel lenses containing the same and silicone hydrogel lenses Korean Patent Registration No. 10-1231181: Silicone Hydrogel Composition for Soft Contact Lens and Soft Contact Lens Produced by the Composition Korean Patent No. 10-1553685: Antibacterial Hydrogel Contact Lens and Manufacturing Method Thereof Korean Patent No. 10-1545757: Manufacturing Method of Hydrogel Contact Lens

It is an object of the present invention to provide an SiONH ₂ reagent prepared by using MA (N, N-dimethylacrylamide) and a SiNH ₂ reagent. Functional hydrogel lens composition capable of adding a material having various functions by using SiONO _2, which is a synthesized silicon monomer, and capable of producing a highly functional silicone hydrogel contact lens having a drug delivery function.

And according to the present invention in order to accomplish the above object, the functional hydrogel lens composition, DMA (N, N-dimethylacrylamide , N, N- dimethylacrylamide), and the acrylic in the SiONH ₂ reagent prepared using reagent ₂ SiNH And SiONO _{2, which} is a silicone monomer synthesized by adding a silane coupling agent.

In addition, the high-functional hydrogel contact lens compositions according to the invention is characterized in that that contains a mixture of the SiONO ₂ -DMA SiONO ₂ and DMA mixture.

The high functional hydrogel contact lens composition according to the present invention is characterized in that the mixing ratio of SiONO ₂ : DMA is 1: 1-3.

Also, the high-performance hydrogel contact lens composition according to the present invention is characterized in that HPMA (hydroxypropyl methacrylate) is further mixed, EGDMA (ethyleneglycol dimethacrylate) is used as a crosslinking agent, and AIBN (azobisisobutyronitrile) do.

Also, the high-performance hydrogel contact lens composition according to the present invention is characterized by further comprising 3-hydroxypyridine.

Also, the high-performance hydrogel contact lens composition according to the present invention is characterized by adding GO (graphene oxide) nanoparticles and polyvinylpyrrolidone (PVP) as a dispersant.

In addition, high-functional hydrogel contact lens compositions according to the present invention, the mixing ratio of ₂ SiONO -DMA is SiONO _2: DMA = 1: a 2 ~ 3, HPMA (hydroxypropyl methacrylate ) is 30 ~ 50wt% based on SiONO ₂ -DMA the 3-hydroxypyridine is mixed with 5 ~ 10 wt% based on SiONO _2- DMA, GO (graphene oxide) is added with 0.05 ~ 1.0 wt% based on SiONO _2- DMA, PVP is mixed with SiONO ₂ -DMA reference being 7 ~ 10wt% is blended, EGDMA is based SiONO ₂ -DMA and 0.5 ~ 1.0wt% is blended, AIBN is characterized in that the reference SiONO ₂ -DMA 0.1 ~ 1.0wt% are blended.

According to the above-described structure, the highly functional hydrogel contact lens composition according to the present invention is obtained by attaching an acrylic group to a SiONH ₂ reagent prepared by using DMA (N, N-dimethylacrylamide, N, N-dimethylacrylamide) and SiNH ₂ reagent By using SiONO _2, which is a synthesized silicon monomer, it is possible to add a material having various functions and to manufacture a high-functional silicone hydrogel contact lens having a drug delivery function.

FIG. 1 is a photograph of a Rehder single-chamber system-O 2 permeometer model 201T used for measurement of oxygen permeability of a contact lens using a high-performance hydrogel contact lens composition according to an embodiment of the present invention.
2 is a photograph (OTG-137) showing a thickness measuring instrument (OTG-137) used for testing a contact lens using a high-performance hydrogel contact lens composition according to an embodiment of the present invention.
Figure 3 is a photograph of a TEMP. & Humidity Chamber (WL1000S model) used to measure the water content of a contact lens using a high-performance hydrogel contact lens composition according to an embodiment of the present invention.
FIG. 4 is an Oxygen permeometer and Permeometer test for calibrating the olarographic oxygen permeability meter (O ₂ permeometer model 201T) used in the measurement of oxygen permeability of a contact lens using a high-performance hydrogel contact lens composition according to an embodiment of the present invention Photos of modules
FIGS. 5A to 5C illustrate a process of calibrating an O ₂ permeometer model 201T used for measuring the oxygen permeability of a contact lens using the high-performance hydrogel contact lens composition according to an embodiment of the present invention Picture
Figure 6 is a photograph of a shaker incubator DS-210SL used for measuring the antibacterial activity of a contact lens using a high-performance hydrogel contact lens composition according to an embodiment of the present invention.
7 is a photograph of a light transmittance meter (Cary 60 UV-vis.) For measuring the light transmittance of a contact lens using a high-performance hydrogel contact lens composition according to an embodiment of the present invention
8 is a photograph of a wettability test apparatus DSA30 (Kruss GMBH, Germany) for wettability test of a contact lens using a high-performance hydrogel contact lens composition according to an embodiment of the present invention
9 is a graph showing an NMR analysis chart of SiONO ₂ -DMA blended in a high-performance hydrogel contact lens composition according to an embodiment of the present invention

Hereinafter, the high-performance hydrogel contact lens composition according to the present invention will be described in detail with reference to the drawings and Examples.

FIG. 1 is a photograph of a Rehder single-chamber system-O 2 permeometer model 201T used for measurement of oxygen permeability of a contact lens using a high-performance hydrogel contact lens composition according to an embodiment of the present invention. FIG. 3 is a photograph showing a thickness gauge (OTG-137) used for testing a contact lens using a high-performance hydrogel contact lens composition according to an embodiment, and FIG. 3 is a cross- Figure 4 is a photograph of TEMP. & Humidity Chamber (WL1000S model) used to measure the water content of a contact lens using a lens composition. Figure 4 shows the oxygen permeability of a contact lens using a high-performance hydrogel contact lens composition according to an embodiment of the present invention in the Polarographic oxygen transmission rate measuring device, and oxygen permeometer permeometer test modules for calibration of (O ₂ permeometer model 201T) using Jin, and Figure 5a to Figure 5c calibration procedure of the olarographic oxygen transmission rate measuring device (O ₂ permeometer model 201T) used for oxygen permeability measurements of the contact lens using a high-functional hydrogel contact lens compositions, in accordance with an embodiment of the present invention FIG. 6 is a photograph of a shaker incubator DS-210SL used for measuring antibacterial activity of a contact lens using a high-performance hydrogel contact lens composition according to an embodiment of the present invention, and FIG. 7 is a photograph FIG. 8 is a photograph of a light transmittance meter (Cary 60 UV-vis.) For measuring the light transmittance of a contact lens using a high-performance hydrogel contact lens composition according to an embodiment of the present invention. A photograph of a wettability test instrument DSA30 (Kruss GMBH, Germany) for the wettability test of a contact lens using a functional hydrogel contact lens composition, 9 is a chart showing NMR analysis of SiONO ₂ -DMA blended in a high-performance hydrogel contact lens composition according to an embodiment of the present invention.

The high-performance hydrogel contact lens composition according to one embodiment of the present invention comprises a SiONH ₂ reagent prepared by using MA (N, N-dimethylacrylamide, N, N-dimethylacrylamide) and SiNH ₂ reagent, SiONO _{2, which} is a silicone monomer, is blended to enable the addition of a material having various functions and an effect of excellent drug delivery function.

In particular, the high-performance hydrogel contact lens composition according to one embodiment of the present invention is characterized by being excellent in antimicrobial activity and ultraviolet ray blocking function by adding 3-hydroxypyridine.

In addition, the high-performance hydrogel contact lens composition according to an embodiment of the present invention is characterized in that wettability is improved by adding graphene oxide (GO) nanoparticles.

Hereinafter, the composition of the present invention will be described in more detail with reference to an embodiment of the present invention and an improved function of the composition according to an embodiment of the present invention.

< Example 1 : Synthesis of silicon monomers>

For the synthesis of silicon used in the high-performance hydrogel contact lens composition according to an embodiment of the present invention, 20 g of SiNH ₂ was first dissolved in 31.9 ml of ethanol, 7.29 g of DMA was added, And stirred for 4 days. After completion of the reaction, the reaction solution was concentrated under reduced pressure to remove ethanol and residual DMA to obtain transparent SiONH ₂ .

Table 1 summarizes the compounding ratio.

- Reaction mechanism

Material Volume eq Mw SiNH2 20g 1eq 279.6 DMA 7.29 g 1.01eq 99.13 EtOH 31.9ml 1.595v -

After the addition of 74 ml of EA (ethyl acetate) to the flask, 18.56 g of SiONH ₂ and 42 ml of aqueous 1.38M NaOH were added to the flask and cooled to 0 ~ 5 ° C. 5.29 g of acryloyl chloride Slowly drop.

The mixture was stirred at 0 to 5 ° C for 1 hour and then at 20 to 25 ° C for 5 hours. After the reaction is completed, the EA layer is separated using a separatory funnel. The organic layer was washed with NaOH aqueous solution twice and then Na ₂ SO ₄ was added thereto. The mixture was stirred for 1 hour and then filtered. The filtrate was concentrated under reduced pressure to obtain transparent SiONO ₂ .

Table 2 summarizes the compounding ratio.

- Reaction mechanism

Material Volume eq Mw SiONH ₂ 18.56 g 1eq 378.73 Acruloyl Cl 5.29 g 1.1eq 90.51 EA 74ml 4v - 1.38M NaOH 42ml 1.1eq 40.00

< Example 2  : Using synthetic silicone Ophthalmology  Lens Manufacturing>

In a high-performance hydrogel contact lens composition according to an embodiment of the present invention, a silicone monomer (SiONO ₂ ) having a hydrophilic group containing an acrylate group is synthesized and then DMA (N, N-dimethylacrylamide) (hydroxypropyl methacrylate) was used, and EGDMA (ethyleneglycol dimethacrylate) was used as a crosslinking agent. The initiator was copolymerized using AIBN (azobisisobutyronitrile).

Silicone hydrogel lenses were prepared by cast molding method and were thermally polymerized at 135 ℃ for 2 hours. The polymerized lens samples were hydrated in 0.9% physiological saline solution for 24 hours, and water content and oxygen permeability (Dk) of the lenses were measured.

Table 3 summarizes the compounding ratio.

Sample SiD * HPMA EGDMA AIBN SiONO ₂ DMA SDH One 1-3 10 to 50%
(SiD standard) 0.5 to 2.0%
(SiD standard) 0.1 to 1.0%
(SiD standard)

* (SIDAAA2: DMA = 1: 1 to 3)

< Example 3  : Measurement of oxygen permeability and water content>

- Oxygen permeability measurement

The instrument used was a Rehder single-chamber system-O2 permeometer model 201T (Rehder Development Company, Castro Valley, California, USA, see Figure 1) and a General Incubator (LIB-030M, Labtech, 4: 2006, Ophthalmic optics - Contact lenses - Part 4: Physicochemical properties of contact lens materials, 4.4.3 Polarographic method.

As a test method, a Rehder single-chamber system was used and a WL1000S model (see Fig. 3) was used as a constant temperature and humidity chamber (TEMP. & Humidity Chamber) to keep the temperature and humidity constant.

The thickness measurement for measuring the oxygen permeability of the lens was also measured using OTG-137 (see Fig. 2) of Bristol, Inc., which uses a non-contact measurement method. A polarographic cell having a radius of curvature of 8.5 mm was used. The test specimen was held in contact with the cathode of the sensor by means of a fixing device, and the front surface of the test specimen was pressed firmly with a nylon net. The O-rings grabbed the nylon mesh to place the functional contact lens between the graphical cell and the nylon mesh. The entire sensor system with the test contact lens was placed in the General Incubator and maintained at a temperature of 35 ° C ± 0.5 ° C and the exposed surface of the test contact lens maintained a moisture saturation of at least 97% relative humidity in the atmosphere. Experimental contact lenses were stored in a saline solution (0.9% NaCl solution) at least 24 hours before testing and equilibrated for at least 2 hours at the test temperature. Using the Rehder single-chamber system, the sensor fixes the experimental contact lens. Measure the current value while the entire system maintains the temperature of 35 ° C ± 0.5 ° C and calculate Dk / t (oxygen permeability) using the following equation Respectively.

- of the device Calibration

1) An oxygen permeometer and permeometer test modules are prepared for the calibration of the O ₂ permeometer model 201T (see FIG. 4).

2) There are three types of permeometer test modules as listed in Table 4, and check each value and tolerance.

No. S / N electric current Voltage Tolerance Picture One TM 202 +1.50 ㎂ +0.75 V +/- 1%

2 TM 203 +15.0 ㎂ -15 V +/- 5%

3 TM 204 +150 ㎂ +15 V +/- 5%

3) Insert test module No. 1 (TM 202) into INPUTS A as shown in FIG. 5A and turn on the power to check the values of the CURRENT and TEMP ° C display windows.

4) As a result of testing the instrument using test module 1 (TM 202), all results were found to be within the tolerance range.

5) Insert the test module No. 2 (TM 203) into INPUTS A as shown in Fig. 5B and turn on the power to check the values of the CURRENT and TEMP ℃ display windows.

6) As a result of testing the instrument using test module No. 2 (TM 203), all results were found to be within the tolerance range.

7) Insert the test module No. 3 (TM 204) into INPUTS A as shown in Fig. 5C and turn on the power to check the values of the CURRENT and TEMP ℃ display windows.

8) The instrument was tested using test module 3 (TM 204), and all results were found to be within the tolerance range.

9) Three test Polarographic oxygen transmission rate measuring device using a module (O ₂ as a result of the calibration of the model 201T permeometer), showed that all of the results have not contain required correction within the range of tolerance.

- Moisture content measurement

Moisture content was measured using the gravimetric method of ISO 18369-4: 2006, Ophthalmic optics - Contact lenses - Part 4: Physicochemical properties of contact lens materials. The water content was expressed as a percentage using the following equation (2) while maintaining the equilibrium at room temperature in standard salt.

- Oxygen permeability and water content measurement results

The oxygen permeability (Dk), which is a characteristic property of the material, was measured in the range of 41.83 to 53.98 × 10 ^-11 (cm ² / sec) (mlO ₂ / ml × mmHg). As the addition amount of HPMA increased, .

The moisture content of SDH was measured as 54.61 ~ 61.02%. As a result of measurement of oxygen permeability and water content, water content and Dk value decreased with increasing amount of HPMA, but shape and size were improved.

Therefore, in the study on the high-functional hydrogel contact lens composition according to one embodiment of the present invention, addition addition experiment was performed based on SDH considering addition of an additive. Table 5 summarizes the measurement results of the oxygen permeability, and Table 6 summarizes the measurement results of the water content.

sample No. Dk


SDH


One 53.33 2 51.48 3 51.54 4 53.98 5 48.83 6 41.83 Average 50.17

sample No. Water Content (%)


SDH


One 61.02 2 60.08 3 59.77 4 61.82 5 57.83 6 54.61 Average 59.19

< Example  4: Development of lens materials with excellent antimicrobial and ultraviolet protection>

For the experiment of the high-performance hydrogel contact lens composition according to an embodiment of the present invention, the pyridine-based material was mixed with the basic mixture, followed by stirring for at least 3 hours.

Samples containing ref. No pyridine monomer and 5 ~ 10% 3-hydroxypyridine in SDH, a silicone hydrogel contact lens, were used as control and experimental groups, respectively, and Escherichia coli and Staphylococcus aureus) was tested for antimicrobial activity.

As a result of measuring the spectral transmittance of 3-hydroxypyridine, it was shown that UV blocking property was excellent. Table 7 shows the compounding ratio of combinations obtained by adding a pyridine monomer to a silicone hydrogel contact lens material.

Sample SiD * HPMA 3-HP EGDMA AIBN SiONO ₂ DMA SDHP One 1-3 10 to 50%
(SiD standard) 5 to 10%
(SiD standard) 0.5 to 2.0%
(SiD standard) 0.1 to 1.0%
(SiD standard)

* (SIDAAA2: DMA = 1: 1 to 3)

- Antimicrobial activity measurement

For the evaluation of antimicrobial activity, samples containing 5 to 10% of 3-hydroxypyridine in a standard combination of pyridine-free monomers and Escherichia coli and Staphylococcus aureus were used as control and experimental groups, respectively. The antimicrobial activity of

For the experiment, 3M Petrifilm ^™ was used as a dry film medium. The bacteria and lenses were added to 0.9% NaCl saline solution for 24 hours, and water was removed. 1 ml of saline solution was applied to the dried film after shaking with the saline solution and the lens corresponding to 9 times of the lens weight, and cultured at 36 ± 1 ° C for 24 hours. An incubator for bacterial culture was a Shacking Incubator DS-210SL (see Fig. 6) from Daewon Science.

- Antimicrobial activity

The antimicrobial activity of Escherichia coli was examined by using SDH containing no pyridine monomer and 5 ~ 10% of 3-hydroxypyridine as control and experimental groups, respectively. (See Table 8).

Ref. (SDH) SDHP (3-hydroxypyridine)

- Light transmittance  Measure

The light transmittance was measured using Agilent's Cary 60 UV-vis. Spectral transmittance instrument (see FIG. 7) and the soft ware used for the analysis was Cary Win UV. The light transmittance was measured in the visible light region and UV-A and UV-B. The transmittance of all rays was expressed as a percentage.

- Light transmittance  Measurement result

As a result of calculating the average value of the spectral transmittance of the manufactured lens, the reflectance was 88.39% in UV-B and 94.02% in UV-A, and 90.38% in visible light transmittance, respectively. When 3-HP (3-hydroxypyridine) was added in proportions, UV-B was measured as 1.28%, UV-A as 22.23% and visible light transmittance as 89.42%. Table 9 summarizes the measured spectral transmittance.

Optical transmittance Sample UV-B UV-A Vis . Ref. 88.39 94.02 90.38 SDHP 1.28 22.23 89.42

< Example  5: Development of lens material having high wettability and dispersion stability>

In order to increase the dispersion stability of GO (graphene oxide), which is highly wettable and nanoparticles to be added in this patent, the contact angle was measured by adding polyvinylpyrrolidone (PVP) as a dispersant to SDHP combination.

The GO (graphene oxide) nanoparticles used in the present invention were polymerized using Sigma-Aldrich. In addition, colloidal graphene oxide is inadequate for use as an additive in ophthalmic lenses. In this experiment, colloidal graphene oxide was removed using a FreeZone 2.5 Liter Benchtop Freeze Dry System at -50 ° C The nanoparticles were converted into powder form and used as additives. Table 10 summarizes the compounding ratio.

Sample SiD * HPMA 3-HP PVP GO EGDMA AIBN SiONO ₂ DMA SDHPP One 1-3 10 to 50%
(SiD standard) 5 to 10%
(SiD standard) 5 to 15%
(SiD standard) 0.05 to 0.2%
(SiD standard) 0.5 to 2.0%
(SiD standard) 0.1 to 1.0%
(SiD standard)

* (SIDAAA2: DMA = 1: 1 to 3)

- wettability measurement

The wettability was measured by the following method using DSA30 (Kruss GMBH, Germany) experimental equipment (see FIG. 8).

1) Experimental contact lenses were stored in standard saline solution (0.9% sodium chloride solution) 24 hours before the minimum test and equilibrated for at least 2 hours at the test temperature.

2) Experimental contact lenses were tested under moist condition and contact angle was measured after removing water only on the surface.

The contact angle of the contact lens was measured using KIMTECH SCIENCE Wipers with little lint. The contact angle of the contact lens was measured after removing the water on the surface of the contact lens.

4) Using a precision syringe module with a precision screw for control, place a 10 mL syringe fixed on the measuring instrument to make a certain amount of water droplets on the end of the needles.

5) After fixing the experimental contact lens on the lens fixing plate, put the droplet on the surface of the contact lens by bringing the contact lens into contact with the droplet formed on the needles by using the up / down adjustment sample stage Minimize the spreading phenomenon.

6) Move to the camera shooting area using the up / down adjustment sample stage, focus using the focus adjuster, and shoot using a digital CCD camera.

7) A contact angle measurement program (surfaceware7) was used to confirm the contact angle and to store the record. The measurement equation is shown in Equation 3 below.

- wettability measurement result

The contact angles of PVP (polyvinylpyrrolidone) were found to be 67.24 ^{° C for} Ref. Without PVP and 47.02 ^{° C} to 31.28 ^{° C} for PVP. The contact angle decreased. As the ratio of PVP increased, the wettability was improved. In addition, when graphene oxide and PVP are added together, dispersion stability is increased and the water molecules of the surface are less attracted to graphene by the bond between nitrogen (N) of PVP and OH group of carboxyl group (COOH) of graphene oxide oxide, the wettability decreased and the wettability tended to increase again as the amount of GO added increased.

- wet functional reactive mechanism

< Example  6: Final formulation for composition &gt;

Finally, a combination satisfying the physical properties of a high-performance silicone hydrogel contact lens developed in the development of a high-performance hydrogel contact lens composition according to an embodiment of the present invention is that a combination of 3-HP, PVP, and GO are added to SDH And the final compounding ratio and photophysical properties were measured and shown. The final compounded sample was designated SDHP2G. Table 11 shows the blend ratios.

Sample SiD * HPMA 3-HP PVP GO EGDMA AIBN SiONO ₂ DMA SDHP2G One 2 to 3 30 to 50%
(SiD standard) 5 to 10%
(SiD standard) 7 to 10%
(SiD standard) 0.05 to 0.1%
(SiD standard) 0.5 to 1.0%
(SiD standard) 0.1 to 1.0%
(SiD standard)

* (SIDAAA2: DMA = 1: 1 to 3)

The optical and physical properties of the silicone hydrogel contact lens prepared in the final formulation were measured to find that the oxygen permeability (Dk) was 50.77 x 10 ^-11 (cm ² / sec) (mlO ₂ / ml x mmHg) 1.55% for UV-B and 18.18% for UV-A, and 87.46% for visible light transmittance, respectively. The water content was 61.37% and the contact angle was 38.47 ^° . In addition, Escherichia coli detection showed excellent antimicrobial activity when compared with conventional SDH. The results of optical and physical properties of the measured silicone hydrogel contact lenses are shown below.

As a result, it is considered that the lens manufactured in the present patent can be used as a material for a high-performance silicone hydrogel lens by manufacturing a contact lens having high oxygen permeability, ultraviolet barrier function, high wettability, high moisture content and antibacterial function. Table 12 summarizes the results of measurement of optical and physical properties of the manufactured lens, and Table 13 shows the results of the antibacterial property test of the produced lens.

sample No. UV-B UV-A Vis . Contact angle ( ^o ) Dk Water Content (%) SDHP2G One 1.38 18.91 88.38 38.24 51.83 61.75 2 1.67 17.36 86.04 39.96 54.28 62.18 3 1.59 18.26 87.96 37.20 46.19 60.17 Average 1.55 18.18 87.46 38.47 50.77 61.37

SDHP2G

The high-performance hydrogel contact lens composition described above and shown in the drawings is only one embodiment for carrying out the present invention, and should not be construed as limiting the technical idea of the present invention. The scope of protection of the present invention is defined only by the matters set forth in the following claims, and the embodiments improved and changed without departing from the gist of the present invention are obvious to those having ordinary skill in the art to which the present invention belongs It will be understood that the invention is not limited thereto.

Claims (7)

DMA (N, N-dimethylacrylamide, N, N- dimethylacrylamide) SiNH and high-functional hydrogel according to one SiONH characterized in that the silicon composite paste acrylic group monomer in the _second reagent formulation is SiONO ₂ prepared using the _second reagent Contact lens composition. The method according to claim 1,
Wherein the SiONO ₂ -DMA mixture is a mixture of SiONO ₂ and DMA. 3. The method of claim 2,
Wherein the mixing ratio of SiONO ₂ : DMA is 1: 1 to 3: 1. The method according to claim 2 or 3,
HPMA (hydroxypropyl methacrylate) is further mixed,
EGDMA (ethyleneglycol dimethacrylate) is used as a crosslinking agent,
Characterized in that the copolymer is copolymerized with AIBN (azobisisobutyronitrile) as an initiator. 5. The method of claim 4,
Wherein the composition further comprises 3-hydroxypyridine. 6. The method of claim 5,
Characterized in that GO (graphene oxide) nanoparticles and polyvinylpyrrolidone (PVP) are added as dispersants. The method according to claim 6,
The mixing ratio of ₂ SiONO -DMA SiONO ₂ is: a 2 ~ 3,: DMA = 1
HPMA (hydroxypropyl methacrylate) is blended with 30 ~ 50wt% based on SiONO _2- DMA,
3-hydroxypyridine is mixed with 5-10 wt% of SiONO _2- DMA,
GO (graphene oxide) is added in 0.05 ~ 1.0wt% based on SiONO _2- DMA,
PVP is mixed with 7 ~ 10 wt% based on SiONO _2- DMA,
EGDMA is mixed with 0.5 ~ 1.0wt% based on SiONO _2- DMA,
And 0.1 to 1.0 wt% of AIBN based on SiONO _2- DMA.

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