KR102609167B1 - Method of Manufacturing Coating Solution for Color Contact Lenses - Google Patents

Abstract

The present invention relates to a method for manufacturing a coating solution for colored contact lenses, and provides a method for manufacturing a coating solution for colored contact lenses with improved physical properties such as biocompatibility, tensile strength, and wettability by containing collagen, a biomaterial, in the coating layer in direct contact with the cornea. It's about.

Description

{Method of Manufacturing Coating Solution for Color Contact Lenses}

The present invention relates to a method for manufacturing a coating solution for colored contact lenses, and more specifically, to manufacturing colored contact lenses with improved physical properties such as biocompatibility, tensile strength, and wettability by containing collagen, a biomaterial, in the coating layer in direct contact with the cornea. It relates to a coating liquid manufacturing method.

Colored contact lenses (hereinafter referred to as colored lenses) refer to contact lenses in which a pigment that supports changing all or part of the wearer's iris color to a selected color is applied to a specific selected area. These colored contact lenses are contact lenses that correct vision and are colored to match the shape of the iris area to change the color of the iris.

These colored lenses, also referred to as cosmetic lenses or circle lenses, can correct vision while providing an external sense of aesthetics, so the demand for them is steadily increasing not only domestically but also overseas. However, a common factor mentioned by consumers of colored lenses is the inconvenience of wearing them for long periods of time. As a result of the survey, many consumers who wore colored lenses for long periods of time experienced side effects such as foreign body sensation, dry eyes, keratitis, and corneal edema.

Specific examples of side effects include conjunctivitis, which causes continuous friction with the inner surface of the eyelid due to defects in the process of applying pigment to the iris coloring area, or the pigment exposed to the outer skin, causing damage to the inner surface of the eyelid. There is a risk that something like this may occur. In addition, the coating solution applied to colored lenses contains organic compounds and organic solvents for uniform mixing with organic pigments and stabilization of viscosity, and these come into direct contact with the cornea and continuously stimulate it.

Many studies are currently underway to reduce these side effects of colored lenses. For example, Republic of Korea Patent Publication No. 10-2020-0107904 introduces a technology that can reduce damage to the eyelids and cornea by reducing the coefficient of friction of contact lenses by adding hydrophilic polymers to the coating liquid for contact lenses, and there is.

However, despite these studies, the problem of wearing colored lenses for a long time still remains to be solved. Accordingly, the present invention has developed a technology that can improve the wearing comfort by improving the hydrophilicity and biocompatibility of the color lens coating layer and at the same time secure the excellent physical properties of the color lens.

The technical problem to be achieved by the present invention is to provide a coating solution for colored contact lenses containing a hydrophilic coating polymer containing collagen, a biomaterial, and colored contact lenses manufactured using the same and having excellent biocompatibility and mechanical properties. .

The technical problem to be achieved by the present invention is not limited to the technical problem mentioned above, and other technical problems not mentioned can be clearly understood by those skilled in the art from the description below. There will be.

In order to achieve the above technical problem, the color contact lens coating solution according to an embodiment of the present invention contains 50 to 50% of a coating polymer containing atelocollagen and hydroxyethyl methacrylate, based on 100 weight of the coating solution for color contact lenses. It contains 95 weight, and the atelocollagen contains 0.1 to 3 weight based on 100 weight of the coating polymer. The atelocollagen is characterized by an endotoxin content of 0.001 to 0.3 EU/ml, a purity of 95% to 99.9%, and a DNA content of 0.0005 to 0.001 ng/ml. The coating liquid has a viscosity of 200 cp to 400 cp.

In addition, the method for producing a colored contact lens coating solution according to an embodiment of the present invention includes the steps of pretreating atelocollagen; Preparing an atelocollagen solution containing the pretreated atelocollagen; Preparing a hydroxyethyl methacrylate solution containing hydroxyethyl methacrylate and an acid; Preparing a mixture by stirring the atelocollagen solution and the hydroxyethyl methacrylate solution; and adding at least one monomer to the mixture and then polymerizing it to form a coating polymer. Includes.

The pretreatment includes soaking the connective tissue of the atelocollagen raw material in an acid solution to expand the connective tissue; pulverizing the expanded connective tissue under acidic conditions and then washing to obtain a collagen matrix; and salt-treating the collagen matrix to extract atelocollagen; It is characterized by including. The pretreated atelocollagen has an endotoxin content of 0.1 to 0.3 EU/ml, a purity of 95% to 99.9%, and a DNA content of 0.0005 to 0.001 ng/ml. In the mixture, the atelocollagen and the hydroxyethyl methacrylate are characterized in having a content ratio of 1:5 to 1:25.

In addition, a colored contact lens according to an embodiment of the present invention includes a lens base layer forming a base of the colored contact lens; A printing layer located on the lens base layer and containing a pigment for color implementation; and a coating layer located on the printed layer and forming a surface in contact with the cornea. It includes, and the coating layer includes a coating polymer containing atelocollagen and hydroxyethyl methacrylate, and the atelocollagen is characterized in that it contains 0.1 to 3 weight compared to 100 weight of the coating polymer. The lens base layer includes a silicone hydrogel polymer, and the silicone hydrogel polymer includes polydimethylsiloxane and dimethylacrylamide in a content ratio of 1:1.5 to 1:2.5. The silicone hydrogel polymer is characterized in that it contains 1 to 30 weight of hydroxyethyl methacrylate based on 100 weight of the total polymer.

According to an embodiment of the present invention, by producing a coating solution for colored contact lenses containing a hydrophilic coating polymer containing collagen, a biomaterial, the biocompatibility of the coating layer of the lens in direct contact with the cornea is improved, and the wearing comfort is improved. The side effects of eye diseases can be significantly reduced.

In addition, by manufacturing colored contact lenses by including the coating layer of the present invention and synthesizing and mixing silicone hydrogel material, which is a lens raw material, the colored contact lenses of the present invention have excellent mechanical properties such as improved biocompatibility, wettability, and tensile strength. Physical properties can be secured at the same time.

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

Figure 1 is a flowchart showing a method for manufacturing a colored contact lens coating solution according to an embodiment of the present invention.
Figure 2 is a schematic diagram showing the structure of a colored contact lens according to an embodiment of the present invention.
Figure 3 is an image showing the results of measuring the purity of atelocollagen according to Example 1 of the present invention.
Figure 4 is a table showing the results of a virus verification test for atelocollagen according to Example 1 of the present invention.

Hereinafter, the present invention will be described with reference to the attached drawings. However, the present invention may be implemented in various different forms and, therefore, is not limited to the embodiments described herein. In order to clearly explain the present invention in the drawings, parts that are not related to the description are omitted, and similar parts are given similar reference numerals throughout the specification.

Throughout the specification, when a part is said to be "connected (connected, contacted, combined)" with another part, this means not only "directly connected" but also "indirectly connected" with another member in between. "Includes cases where it is. Additionally, when a part is said to “include” a certain component, this does not mean that other components are excluded, but that other components can be added, unless specifically stated to the contrary.

The terms used herein are only used to describe specific embodiments and are not intended to limit the invention. Singular expressions include plural expressions unless the context clearly dictates otherwise. In this specification, terms such as “comprise” or “have” are intended to indicate the presence of features, numbers, steps, operations, components, parts, or combinations thereof described in the specification, but are not intended to indicate the presence of one or more other features. It should be understood that this does not exclude in advance the possibility of the existence or addition of elements, numbers, steps, operations, components, parts, or combinations thereof.

Hereinafter, embodiments of the present invention will be described in detail with reference to the attached drawings.

<Coating liquid for colored contact lenses>

The coating solution for colored contact lenses of the present invention includes a coating polymer containing atelo collagen and hydroxyethyl methacrylate (HEMA). The coating solution can form a coating layer on the inner surface of the colored contact lens that is in direct contact with the cornea.

Specifically, the coating polymer may be formed by forming a copolymer of the atelocollagen and the hydroxyethyl methacrylate hydrophilic monomer. The coating polymer is a hydrophilic natural polymer containing atelocollagen, and exhibits excellent biocompatibility, minimizing irritation when the coating layer directly contacts the cornea, thereby providing excellent wearing comfort even when the lens is used for a long time.

The atelocollagen is collagen obtained by removing the antigenic telopeptide portion from porcine skin. When the atelocollagen is applied to a lens coating solution, biocompatibility can be further improved compared to existing synthetic collagen.

The atelocollagen may be included in an amount of 0.1 to 3 parts by weight, specifically, 0.1 to 2 parts by weight, and more specifically, 0.1 to 1 part by weight, based on 100 weight of the coating polymer. If the content of the atelocollagen is less than 0.1 parts by weight or more than 3 parts by weight, it may not be uniformly mixed with the coating polymer.

The endotoxin content of the atelocollagen may be less than 0.3 EU/ml, for example, 0.1 to 0.3 EU/ml. The purity of the atelocollagen may be 95% or more, for example, 95% to 99.9%. The DNA content in the atelocollagen may be less than 0.001 ng/ml, for example, in the range of 0.0005 to 0.001 ng/ml. If the atelocollagen has the above-mentioned characteristics, when applied to a coating solution for colored contact lenses, the body's immune response to atelocollagen can be significantly lowered, thereby improving biocompatibility.

The coating polymer may be included in an amount of 50 to 95 parts by weight, for example, 50 to 90 parts by weight, specifically 50 to 75 parts by weight, and more specifically 65 to 70 parts by weight, based on the total weight of 100 weight of the coating solution. In addition to the coating polymer, the coating solution may further include additives such as a polymerization initiator, viscosity modifier, and pH adjuster, a solvent, and a remaining amount of purified water.

The viscosity of the coating liquid may be 200 cp to 400 cp. Coating solutions containing atelocollagen may have lower viscosity than existing coating solutions. This may be due to the process of treating atelocollagen with a weak acid to apply it as a polymer in a stirrable form.

Figure 1 is a flowchart showing a method of manufacturing a coating solution for colored contact lenses according to an embodiment of the present invention.

Referring to Figure 1, the method for producing the coating solution for colored contact lenses includes a first step of pretreating atelocollagen; A second step of preparing an atelocollagen solution; A third step of preparing a hydroxyethyl methacrylate solution containing hydroxyethyl methacrylate and an acid; A fourth step of preparing a mixture by stirring the atelocollagen solution and the hydroxyethyl methacrylate solution; and a fifth step of adding at least one monomer to the mixture and then polymerizing it to form a coating polymer. Includes.

Hereinafter, the coating liquid manufacturing method will be described in more detail for each step.

In the first step, the pretreatment process includes soaking the connective tissue of the collagen raw material in an acid solution to expand the connective tissue (dermis or tendon); Grinding the expanded connective tissue under acidic conditions and then washing it to obtain a collagen matrix; extracting collagen from the collagen matrix; Includes.

To be more specific, the connective tissue refers to the dermis or tendons of pigs, which are the raw materials for the atelocollagen. The acid of the acid solution may be formic acid, oxalic acid, acetic acid, citric acid, lactic acid, malic acid, phosphoric acid, or a mixture thereof. For example, the acid solution may be an acetic acid solution. The immersion may be performed for 20 to 28 hours, for example, 24 hours. The immersion can be performed at a refrigerated temperature, for example, in the range of 0° C. to 15° C. to inhibit the growth of microorganisms. Ultrasonic treatment may be performed during the immersion.

The pulverization may be to homogenize the connective tissue by pulverizing the expanded connective tissue using a homogenizer or the like under acidic conditions (PH 3 to 5). The grinding process can increase the purity of atelocollagen by removing cell nuclei and DNA in atelocollagen, and further increase biocompatibility to the human body by inactivating viruses in collagen.

The washing may be washing the homogenized connective tissue in a washing solution containing a detergent, a proteolytic enzyme such as pepsin, or a mixture thereof. By washing, non-collagenous substances can be removed from the homogenized connective tissue to obtain a collagen matrix. Ultrasonic treatment may be performed during the cleaning.

The step of extracting atelocollagen from the collagen matrix may involve obtaining high-purity collagen by subjecting the collagen matrix to salt treatment. The salt may be, for example, sodium chloride or potassium chloride, but is not limited thereto. At least one filtration may be performed during the extraction process.

The first step, that is, the pretreatment process, can improve the purity of atelocollagen and minimize immune reactions, and has the effect of improving the compatibility of atelocollagen and monomers during the subsequent polymerization reaction.

The atelocollagen, specifically, the atelocollagen that has undergone a pretreatment process, may have an endotoxin content of less than 0.3 EU/ml, for example, 0.1 to 0.3 EU/ml. The purity of the atelocollagen may be 95% or more, for example, 95% to 99.9%. The DNA content in the atelocollagen may be less than 0.001 ng/ml, for example, in the range of 0.0005 to 0.001 ng/ml. If the atelocollagen has the above-mentioned characteristics, it can minimize the immune response to the human body and exhibit excellent biocompatibility when applied to a coating solution for colored contact lenses.

In the second step, in order to inactivate the enzymatic reaction of the pre-treated atelocollagen, the pH is raised to about pH 8 by mixing a basic solution and distilled water, and after reacting for a certain period of time, an acidic solution (HCl solution) is added again. An atelocollagen solution is prepared by lowering the pH to about 3. Thereafter, the atello collagen solution may be filtered using, for example, a microfilter.

In the third step, the hydroxyethyl methacrylate solution may be obtained by mixing hydroxyethyl methacrylate with an acidic aqueous solution. The acid of the acidic aqueous solution may be formic acid, oxalic acid, acetic acid, citric acid, lactic acid, malic acid, phosphoric acid, or a mixture thereof, but is not limited thereto. For example, the acidic aqueous solution may be an aqueous formic acid solution.

In the fourth step, a mixture of the atelocollagen solution of the second step and the hydroxyethyl methacrylate solution of the third step is prepared. The mixing may be performed, for example, at 10°C to 35°C for 1 hour to 8 hours. The atelocollagen and the hydroxyethyl methacrylate are, for example, 1:5 to 1:25, specifically, 1:15 to 1:22, in another example, 1:1.5 to 1:1:75, specifically. It can be mixed at an content ratio of 1:3.5 to 1:5.5. The mixing allows the atelocollagen to form a uniform mixture with the hydroxyethyl methacrylate under acidic conditions, so that during the subsequent polymerization of the coating polymer, the atelocollagen demonstrates excellent compatibility with the monomer. This makes it easier to form the coating polymer.

The monomer in the fifth step may be at least one hydrophilic monomer, at least one hydrophobic monomer, or a mixture thereof. The hydrophilic monomer can further improve the hydrophilicity of the coating polymer to be formed later. The hydrophilic monomer is at least one selected from acrylic monomers such as methacrylate (MA), methyl methacrylate (MMA), 2-hydroxyethyl methacrylate, and hydroxypropyl methacrylate, or It may be at least one selected from allyl-based monomers such as allyl alcohol and allyl glucol carbonate, or a mixture thereof. However, it is not limited to this. For example, the hydrophilic monomer may be a mixture of methacrylate (MA) and methyl methacrylate (MMA).

The hydrophobic monomers include 4-methacryloxy-2-hydroxybenzophenone, ethyl-3 benzoyl acrylate, N-propyl methacrylate, styrene, and glycidyl methacryl. It may be at least one selected from glycidyl methacrylate and N-butyl acetate. For example, the hydrophobic monomer may be 4-methacryloxy-2-hydroxybenzophenone.

The monomer may be included in an amount of 10 to 50 weight based on 100 weight of the mixture in the fourth step.

For example, the polymerization may be performed at 25°C to 70°C for 10 to 50 minutes. The polymerization can form a hydrophilic coating polymer for colored contact lenses containing atelocollagen. During the polymerization, additives such as polymerization initiator and crosslinking agent may be further included.

For example, the coating polymer may include 50 to 95 weight, for example, 50 to 75 weight, for example, 65 to 70 weight, based on 100 weight of the total coating liquid for colored contact lenses.

In addition to the coating polymer, the coating solution for colored contact lenses may further include a viscosity modifier, which is an additive included in a typical coating solution for lenses, and a remaining amount of solvent.

<Colored contact lenses>

Figure 2 is a schematic diagram showing the colored contact lens of the present invention.

Referring to Figure 2, the color contact lens of the present invention includes a lens base layer 30 forming the base of the color contact lens; A printing layer 20 located on the lens base layer and containing a pigment for color implementation; and a coating layer (10) located on the printed layer and forming a surface in contact with the cornea. It includes, and the coating layer includes a coating polymer of atelocollagen and hydroxyethyl methacrylate, and the atelocollagen is characterized in that it contains 0.1 to 3 parts by weight based on 100 weight of the coating polymer.

The manufacturing method of the colored contact lenses is as follows.

The coating layer can be formed by printing and curing the colored contact lens coating solution of the present invention on the surface of a contact lens-shaped mold. The printing layer can be manufactured by printing an ink composition containing pigment and dye on the coating layer and then curing it.

The lens base layer can be manufactured by printing and curing a solution containing a polymer that forms the main body of the lens on the printing layer. The polymer may be, for example, a silicone hydrogel polymer. Specifically, the silicone hydrogel polymer may include a silicone polymer and a hydrophilic monomer.

For example, the silicone polymer may be formed by polymerizing polydimethylsiloxane (PDMS) and dimethylacrylate (DMA). The mixing ratio of polydimethylsiloxane (PDMS) and dimethylacrylate (DMA) may be, for example, 1: 1.5 to 1: 2.5, specifically, 1: 1.7 to 1: 2.3, for example, 1: 2. there is. The above mixing ratio range has the effect of increasing the moisture content and wettability of lenses manufactured later.

For example, the hydrophilic monomer may be hydroxyethyl methacrylate (HEMA; 2-hydroxyethyl methacrylate). The hydroxyethyl methacrylate (HEMA; 2-hydroxyethyl methacrylate) polymer has a -OH group, a hydrophilic group, terminated at the end, which can further increase the moisture content of the formed lens.

The hydrophilic monomer may be included in an amount of 1 to 30 weight, for example, 5 to 30 weight, specifically, 12 to 28 weight, for example, 20 weight, based on the total 100 weight of the silicone hydrogel polymer.

When the silicone polymer and the hydrophilic monomer have a mixing ratio within the above-mentioned range during polymerization, mechanical properties such as moisture content, wettability, and tensile strength of the manufactured lens can be improved.

The silicone hydrogel polymer is, for example, methyl methacrylate (MMA), methacrylate (MA), ethylene glycol dimethacrylate (EGDMA), 0 azobicysobutyronitrile (AIBN), 1,1- 1,1-Dimethyl-2-propynyl)oxy]trimethylsilane), (3-Methacrylamidopropyltris(trimethylsiloxy)silane) ), tris(2methoxyethoxy)vinylsilane, and vinyltriethoxysilane. It may further include at least one additive selected from the group consisting of vinyltrimethoxysilane.

The additive may be included in an amount of 0.1 to 20 weight, in another example, 0.1 to 5.0 weight, and in another example, 0.1 to 1.0 weight, based on 100 weight of the silicone hydrogel polymer.

When the additives are mixed when manufacturing the silicone hydrogel polymer, mechanical properties such as moisture content, wettability, and tensile strength of the manufactured lens can be further improved.

The visible light transmittance of the colored contact lenses is 95% or more, for example, 95% to 99.9%, the water content is 40% or more, for example, 40% to 55%, specifically, 50% to 55%, and the contact angle is 40º or less, for example, 33º or more to 40º or less, and the tensile strength may exhibit physical properties of 0.2 kgf or more, for example, 0.203 kgf to 0.260 kgf.

<Example 1: Preparation of coating solution for colored contact lenses>

1. Atelocollagen pretreatment and selection

Pretreatment

The pork skin was swollen by immersing it in 0.5M acetic acid at refrigerated temperature (1°C) for 24 hours, and then frozen in the freezer for more than 1 hour. After physically removing the fat from the pork skin with a knife, it was washed with purified water, dehydrated using a sieve, weighed 500g, and stored frozen for about 3 hours. Then, the pork skin was homogenized by pulverizing it using a homogenizer. After mixing 500 g of homogenized pork skin with 50 L of 0.5 M acetic acid, the mixture was stirred for 24 hours under refrigerated (1°C) conditions, and 10% of pepsine based on the total weight of the pork skin was added and reacted. Next, the gelated collagen (collagen matrix) was harvested using a centrifuge and then diluted to 4% while measuring the water content. Afterwards, the container was sterilized on a clean bench and sealed to prevent air from entering.

Next, to inactivate the enzyme reaction, the sample was reacted with sodium hydroxide (NaOH) (pH 8) for about 1 hour and then adjusted to pH 3 using HCl. Then, primary filtration was performed using a filter with a pore size of 1.0 μm, and secondary filtration was performed using a filter with a pore size of 0.75 μm. The sample, which was filtered once more, was placed in a semi-finished product container (SUS tank) and then coagulated by adding salt (NaCl). To harvest collagen after salting out, centrifugation was performed for 1 hour and only pure collagen was collected using a pellet. Afterwards, to remove NaCl from collagen, it was dialyzed against 20L of 0.5M acetic acid under refrigerated conditions (1°C). Collagen that had gone through the dialysis process was diluted 10 times with 0.5M acetic acid for filtration. Afterwards, the third filtration was performed using a 0.45㎛ filter, and the fourth filtration was performed using a 0.22㎛ filter. Next, it was concentrated using a TFF dedicated filter, and the concentrated collagen solution was gelled under pH 4.5 conditions using NaOH.

go. Atellocollagen selection and purity measurement for colored contact lenses

High purity control group and atelocollagen according to the example were obtained using SDS-PAGE method.

Purity was compared.

Figure 3 is an image showing the results of measuring the purity of atelocollagen according to Example 1. Referring to Figure 3, as a result of the test, the thickness and type of protein band shown through protein separation of the high-purity atelocollagen sample as a control and the atelocollagen of Example 1 were similar, so compared to the control group, the high-purity atelocollagen sample was similar. It was confirmed that it was local collagen.

me. Measurement of DNA and nuclear content

Two groups of 50g of pork skin from which fat was removed were prepared and the grinding process was applied in D.W and ascorbic acid environments, respectively. Afterwards, the sample was fixed and quantitative DNA measurement was performed using DAPI staining to stain the cell nucleus blue and a Genomic DNA branching kit to quantitatively confirm the remaining DNA concentration.

As a result, in the group exposed to ascorbic acid and pulverized, all cell components were pulverized and decomposed by acid, so there was almost no DAPI reaction. On the other hand, in the group where pork skin was placed in D.W and ground, a large amount of cell nuclei were confirmed in the tissue of the ground product. Through this test, it can be confirmed that cell nuclei, which are immune-reactive substances, are efficiently removed during the acid grinding step.

Meanwhile, about 200ng/ml of genomic DNA was detected in the group where pork skin was placed in D.W. and ground, and in the group where pork skin was exposed to and ground ascorbic acid, less than about 0.0005ng/ml of genomic DNA was detected. Through this test, it was confirmed that DNA, an immune response material, was efficiently removed during the acid grinding step.

all. Virus inactivation verification test

6 types of pig-derived viruses (porcine adenovirus: ｐADV, porcine parvovirus: PPV, transmissible gastroenteritis virus: TGEV, porcine hamagglutinating encephalomyelitis virus: PHEV, porcine rotavirus: PRoV, pesudorabies virus: PRV) real test using TaqMan probe to check for contamination -Time PCR was used to detect DNA of pig-derived viruses pADV, PPV, and PRV, and RNA of TGEV, PHEV, and PRoV in pig-derived collagen (Q5A ICH guideline and Ministry of Food and Drug Safety Biologics Evaluation Guide “Validation of nucleic acid amplification test method”) (Performed using a validated TaqMan probe real-time PCR test method based on “Guidelines”).

Figure 4 is a table showing the results of the virus verification test of atelocollagen according to Example 1. Referring to FIG. 4, porcine viral DNA and RNA were not detected in the atelocollagen according to Example 1, confirming that it was not contaminated with porcine-derived viruses.

2. Coating liquid production

An atelocollagen solution was prepared by mixing 0.5 g of atelocollagen that had undergone the above-described pretreatment with 2 ml of 1 M formic acid solution. Meanwhile, a HEMA solution was prepared by mixing 10 g of hydroxyethyl methacrylate (HEMA) with 5 ml of 1 M formic acid solution, and then stirred with the atelocollagen solution to prepare a mixture. (At this time, the mixing ratio of HEMA and atelocollagen was 20:1) Next, hydrophilic and hydrophobic monomers were added to the mixture and stirred, and then 0.7 g of polymerization initiator and 1 g of crosslinking agent were added to prepare a coating polymer. A coating solution for lenses (viscosity: 231 cp) was prepared by further including a solvent and a viscosity modifier in addition to the coating polymer.

<Example 2: Manufacturing colored contact lenses>

Silicone hydrogel polymer preparation

Polydimethylsiloxane (PDMS) 1g, dimethylacrylamide (DMA) 2g, hydroxyethyl methacrylate (HEMA) 0.6g, Tris 0.9g, methyl methacrylate (MMA) 0.04g, methacrylate (MA) 0.02g , 4.596 g of silicone hydrogel polymer (HEMA-Co-urethane-co-polydimethylsiloxane) was prepared by mixing 0.03 g of ethylene glycol dimethacrylate (EGDMA) and 0.006 g of azovisisobutyronitrile (AIBN).

Colored contact lenses manufacturing

1 mg of the coating solution prepared in Example 1 was printed on the surface of the ball mold and then cured to prepare a coating layer. Next, a printed layer was prepared by printing 2.1 mg of pigment on the coating layer. Thereafter, a polymer solution containing 1 g of the silicone hydrogel polymer (HEMA-Co-urethane-co-polydimethylsiloxane), 0.62 g of hydrophilic monomer, and 2.94 g of hydrophobic monomer was coated on the printing layer, and then subjected to a polymerization process (100° C. , 1 hour) and then cured to prepare a lens base layer.

<Experimental example: Comparison of physical properties of lenses according to mixing ratio in silicone hydrogel polymer>

The moisture content, refractive index, and wettability of the lens were measured and compared according to the mixing ratio of the ingredients in the silicone hydrogel polymer.

Table 1 shows the compositions of Preparation Examples 1 to 6 prepared by varying the mixing ratio of DMA in PDMS_A, a silicone hydrogel polymer (HEMA-Co-urethane-co-polydimethylsiloxane), and PDMS_B, a control group without urethane. The results of measuring the refractive index and water content of the lens manufactured by Preparation Example 1-6 are shown. Table 2 shows the compositions of Preparation Examples 7 to 12 prepared by varying the content of HEMA.

Referring to Tables 1 and 2, the refractive index increased as the amount of PDMS increased, regardless of the PDMS synthesis method. It was confirmed that PDMS_A had a higher refractive index than PDMS_B. As a result of measuring the moisture content, PDMS_A was 50.47%, 54.79%, and 41.84%, respectively, and PDMS_B was 55.25%, 59.68%, and 48.54%, respectively, depending on the mixing ratio. It can be confirmed that this is inversely proportional to the refractive index. Among them, Preparation Example 2 showed excellent physical properties with a moisture content of 54.79%. On the other hand, when HEMA was contained in an amount of 15 to 25 weight, for example, 20 weight, based on the total weight of the polymer, water content and wettability were excellent.

<Evaluation example: Evaluation of physical properties of colored contact lenses>

Physical property evaluation tests (visible light transmittance, water content, contact angle, and tensile strength measurement tests) of the colored contact lenses manufactured in Example 2 were performed. The specific measurement methods are described below. In addition, the Atello test of the colored contact lenses manufactured was performed. Endotoxin, purity, DNA content, and cytotoxicity of collagen were measured, and lens wearing comfort (eye irritation, skin sensitization) was evaluated. The results are shown in Table 3 below.

Visible light transmittance

Measurements were made using Agilent Technologies Cary 60. For the experimental sample, a sufficiently hydrated lens was placed in a measurement cuvette along with a standard physiological saline solution of ISO 18369-3. Surface moisture of the sample was removed using a portion Whatman #1 filter paper, and then UV-B, UV-A, and visible light were applied. Each area was measured.

moisture content

It was measured using the Gravimetric method based on ISO1869-4:2006 (Ophthalmic optics-Contact lenses-Part 4: Physicochemical properties of contact lens materials).

contact angle

The contact angle was measured using a contact angle meter to measure the hydrophilicity of the lens surface. Distilled water was dropped on the surface of a sample prepared by the sessile drop method at room temperature, the spreading angle was measured, and the difference was compared with the average value.

tensile strength

The tensile strength was measured for a contact lens product group manufactured using a jig with a curvature specifically for contact lenses and a developed support exclusively for contact lenses (ASTM).

Referring to Table 3, it can be seen that the contact lens according to Example 2 shows excellent biocompatibility and has excellent physical properties such as tensile strength and moisture content.

The description of the present invention described above is for illustrative purposes, and those skilled in the art will understand that the present invention can be easily modified into other specific forms without changing the technical idea or essential features of the present invention. will be. Therefore, the embodiments described above should be understood in all respects as illustrative and not restrictive. For example, each component described as single may be implemented in a distributed manner, and similarly, components described as distributed may also be implemented in a combined form.

The scope of the present invention is indicated by the claims described below, and all changes or modified forms derived from the meaning and scope of the claims and their equivalent concepts should be construed as being included in the scope of the present invention.

10: coating layer 20: printing layer
30: Lens base layer

Claims (4)

Pretreating atelocollagen;
Preparing an atelocollagen solution containing the pretreated atelocollagen;
Preparing a hydroxyethyl methacrylate solution containing hydroxyethyl methacrylate and an acid;
Preparing a mixture by stirring the atelocollagen solution and the hydroxyethyl methacrylate solution; and
Adding at least one monomer to the mixture and then polymerizing it to form a coating polymer; Including,
The pretreatment includes soaking the connective tissue of the collagen raw material in an acid solution to expand the connective tissue;
Grinding the expanded connective tissue under acidic conditions and then washing it to obtain a collagen matrix; and
Comprising: extracting atelocollagen from the collagen matrix,
The connective tissue is dermis or tendon,
The monomer is at least one type of hydrophilic monomer, at least one type of hydrophobic monomer, or a mixture thereof,
The hydrophilic monomer is at least one selected from acrylic monomers including methacrylate (MA), methyl methacrylate (MMA), 2-hydroxyethyl methacrylate, and hydroxypropyl methacrylate. ; It is at least one selected from allyl-based monomers including allyl alcohol and allyl glucol carbonate; or a mixture thereof;
The hydrophobic monomers include 4-methacryloxy-2-hydroxybenzophenone, ethyl-3 benzoyl acrylate, N-propyl methacrylate, styrene, and glycidyl meta. At least one selected from glycidyl methacrylate and N-butyl acetate,
A method for producing a colored contact lens coating solution, characterized in that the atelocollagen and the hydroxyethyl methacrylate in the mixture have a content ratio of 1:5 to 1:25.
In claim 1,
The preprocessing is,
A step of soaking the connective tissue of the atelocollagen raw material in an acid solution to expand the connective tissue;
pulverizing the expanded connective tissue under acidic conditions and then washing to obtain a collagen matrix; and
Extracting atelocollagen by treating the collagen matrix with salt; A method for manufacturing a colored contact lens coating solution comprising: In claim 2,
The pretreated atelocollagen,
A method for producing a colored contact lens coating solution, characterized in that the endotoxin content is 0.1 to 0.3 EU/ml, the purity is 95% to 99.9%, and the DNA content is 0.0005 to 0.001 ng/ml. delete