TWI690424B - Method for preparing contact lens with polymer multilayer film - Google Patents

Abstract

A method for preparing a contact lens with a polymer multilayer film is to attach a polymer film to the surface of the lens body through chemical conjugation, and then use the ion adsorption between the negative charge and the positive charge of the polymer substance to produce another A polymer film to form a polymer multilayer film with a good combination of two polymer films on the surface of the lens body; when contact lenses are worn, this polymer multilayer film will provide a smoother touch to the surface of the eye, while achieving Higher water content, which can improve the wearing comfort.

Description

Method for preparing contact lens with polymer multilayer film

The invention relates to a method for preparing a contact lens, in particular to a method for preparing a contact lens with a polymer multilayer film.

The main problem associated with the use of contact lenses is dryness. Therefore, it has become a trend to increase the use of higher air permeability materials in the manufacture of contact lenses, which also promotes the use of siloxane-based materials. On the other hand, these materials are hydrophobic in nature and repel water. Even if plasma is used for surface treatment to form a hydrophilic surface, these lenses may form water-repelling areas, which may lead to a reduction in water-breakup time. These areas also have a tendency to attract more lipid and protein deposits.

To improve these problems, contact lenses can be coated with the required materials. The coating material can be selected according to the desired properties. Generally, hydrophilic polymers have been used in the medical field to prevent undesirable immunogenic reactions when the polymer enters the body. It can be easily seen that PEGylation of insulin is a very ideal way to avoid the immunogenic reaction when it enters the body. Similarly, coating with hydrophilic polymers has also been used to protect the surface of medical devices to avoid suffering from aggregation of proteins on the surface.

Based on these experiences, it is also useful to coat the surface of the contact lens with the desired material, which can prevent adverse effects such as protein deposits. In a practical example, the surface of a contact lens made of a hydrophobic material may be coated with a layer of hydrophilic material. For example, the hydrophobic material can be silicon, which is used to manufacture the body of the lens, and the hydrophilic monomer can be poly(methacrylate), which can be used to coat the surface of the contact lens. This coating can provide hydrophilic properties to the surface of the contact lens.

Therefore, this coating method can be used to provide the desired characteristics of the body of the contact lens. Furthermore, the main body of the contact lens can maintain the overall properties of the material from which it is made, while only modifying the surface can ensure that the physical characteristics of the entire contact lens are not affected. For the multi-layer coating on the surface of contact lenses, a hydrophilic surface can be made and bring more functionality to the coating, such as anti-reflection, anti-fog, anti-ultraviolet and so on. A method of manufacturing a multilayer coating is known, in which at least two different polyelectrolytes of opposite charges are alternately formed on a substrate to form a layer-by-layer (LbL) coating. However, this layer-by-layer coating has poor adhesion to the substrate.

In view of this, the main purpose of the present invention is to provide a method for preparing a contact lens with a polymer multilayer film, which combines a technology capable of chemically conjugating one or more polymers on the surface of the lens body, and uses different charged substances A variety of polymers are used to make a layer-by-layer coating method, and a polymer multilayer film composed of a chemically conjugated polymer film and an ion-bonded polymer film can be formed on the surface of the lens body. The polymer multilayer film can be Wearers of contact lenses provide benefits such as increased water retention and comfort.

Another object of the present invention is to provide a method for preparing a contact lens with a polymer multilayer film, which can be achieved by using the existing manufacturing process and production line of contact lenses, which can reduce equipment costs and is highly economical.

In order to achieve the above object, the present invention provides a method for preparing a contact lens with a polymer multilayer film. First, a lens body is provided, and a plurality of chemical groups exist on the surface of the lens body; then, a reaction solution is provided, and at least a first A polymer is added to the reaction solution, and the first polymer contains a negative charge; the lens body is immersed in the reaction solution, and under the action of an ultraviolet light source or a heat source, the first polymer is chemically conjugated to the surface of the lens body to form the first polymer Film; then provide a buffer solution, add at least a second polymer to the buffer solution, the second polymer contains a positive charge; and, immerse the lens body in the buffer solution to form a second polymer film through the ion adsorption process Yu First Polymer On the surface of the film, a polymer multilayer film including a first polymer film and a second polymer film is formed on the surface of the lens body.

In the foregoing preparation method, in order to perform the chemical conjugation process on the surface of the lens body, the lens body must have some chemical groups, and these chemical groups may preferably be amine groups, carboxyl groups, or sulfonate groups (sulfone group), for example, the lens body can be composed of a monomer containing Ethanolamine, Dopamine, Octadecylamine or N,N-Dimethylacrylamide be made of. The first polymer is preferably selected from modified and unmodified polyethylene glycol (Polyethylene glycol), hyaluronic acid, sodium hyaluronate, N-vinylpyrrolidone (N -vinylpyrrolidone), polyvinyl alcohol (Poly (vinyl alcohol)), 2-methacryloyloxyethyl phosphorylcholine (2-methacryloyloxyethyl phosphorylcholine), poly (acrylamide) (Poly (acrylamide)), seaweed One or more of Alginic acid and sodium alginate.

In the aforementioned preparation method, in order to perform a layer-by-layer deposition process on the surface of the lens body, the second polymer has a charge opposite to that of the first polymer, and the second polymer is preferably selected from hyaluronic acid and hyaluronic acid One or more of sodium, alginic acid, sodium alginate, modified and unmodified chitosan (Chitosan).

In the aforementioned preparation method, all reactions can be allowed to take place in a small container suitable for lens storage, without adding additional basic equipment, and can ensure all reaction steps. Specifically, the lens body may be additionally stored in a first container, the first container is filled with a reaction solution, the reaction solution contains the first polymer needed to coat the first polymer film, and the reaction solution may further contain A suitable catalyst to promote the reaction is then sealed and allowed to react in the form of ultraviolet light or temperature to form a first polymer film. Similarly, after the above reaction is completed, the lens body can be transferred to a second container, which is filled with a buffer solution, and the buffer solution contains a second polymer for forming a second polymer film On the first polymer film. Then, the second container is sealed and sterilized by moist heat, that is, it can be sold to customers to ensure comfortable wearing of the lens. In this way, the present invention can use existing processes and equipment to reduce costs and maximize benefits.

The detailed description will be given below through specific embodiments, so that it is easier to understand the purpose, technical content, characteristics and achieved effects of the present invention.

10: Lens body

11: Catalyst

20: reaction solution

30: buffer solution

FIG. 1 is a flowchart of a method for preparing a contact lens with a polymer multilayer film provided by the present invention.

2A~2F are schematic flow charts of the method for preparing a contact lens with a polymer multilayer film provided by the present invention.

Please refer to FIG. 1 to illustrate the process steps of the method for preparing a contact lens with a polymer multilayer film provided by the present invention; meanwhile, please refer to FIGS. 2A to 2F to sequentially illustrate the polymer multilayer provided by the present invention Schematic diagram of the preparation method of the film contact lens.

First, see step S100. As shown in FIG. 2A, a lens body 10 is provided. The lens body 10 is made of monomers rich in chemically active groups, and there are Multiple chemical groups.

In the present invention, contact lens refers to an optical or medical article manufactured using any monomer common in the contact lens industry. It is well known to those skilled in the art that the monomer materials used to manufacture the lens body 10 of such contact lenses include common hydrophilic monomers (such as poly-2 (hydroxyethyl methacrylate) (pHEMA, Poly-2 ( hydroxyethyl methacrylates), hydrophobic monomers (such as silicones), or a combination of the two. This type of contact lens is made by lathe-cutting, cast-molding, such as lathe-cutting ), spin casting (spin casting) or any other combination method derived from the aforementioned method, and simultaneously with heat curing or ultraviolet (UV) Any combination of curing methods.

At the same time, the monomer material of the lens body 10 for manufacturing contact lenses of the present invention must have some chemical groups. These chemical groups can be used to conjugate the desired polymer to the lens body surface. The reaction type of the conjugated polymer can be selected according to the chemical properties of the chemical groups present on the surface of the lens body 10 and the polymer expected to be conjugated on the surface. Furthermore, a suitable reaction environment can be designed according to the chemical groups. The desired catalyst can also be selected; as shown in Figure 2B, the catalyst 11 can be used for activation.

In the present invention, the chemical group may be an amine group, a carboxyl group, or a sulfone group. The lens body 10 can be made of a monomer mixture containing Ethanolamine, Dopamine, Octadecylamine or N,N-Dimethylacrylamide.

Then, referring to step S110, a reaction solution 20 is provided, at least one first polymer is added to the reaction solution 20, the first polymer contains a negative charge, and the first polymer has a plurality of chemistry that can exist on the lens body 10 A chemical group in which a group reacts and is conjugated.

In the present invention, the first polymer may be selected from modified and unmodified polyethylene glycol (Polyethylene glycol), hyaluronic acid (hyaluronic acid), sodium hyaluronate, N-vinylpyrrolidone (N-vinylpyrrolidone), polyvinyl alcohol (Poly(vinyl alcohol)), 2-methacryloyloxyethyl phosphorylcholine, poly(acrylamide) , One or more of alginic acid and sodium alginate.

In step S120, as shown in FIG. 2C, the lens body 10 is immersed in the reaction solution 20. As shown in FIG. 2D, under the action of an ultraviolet light source or a heat source, the chemical groups of the lens body 10 and the first polymer will A reaction is performed to form a stable covalent bond between the surface of the lens body 10 and the first polymer to achieve chemical conjugation, and the surface of the lens body 10 The first polymer film is formed on the surface.

In step S130, a buffer solution 30 is provided, and at least one second polymer is added to the buffer solution 30. The second polymer contains a positive charge.

In the present invention, the second polymer may be selected from one or more of hyaluronic acid, sodium hyaluronate, alginic acid, sodium alginate, modified and unmodified chitosan (Chitosan).

In the present invention, the buffer solution 30 refers to a solution for storing the contact lens in its polypropylene package before the contact lens is sold and used. This solution basically consists of an aqueous buffer combined with other reagents to ensure an osmotic pressure compatible with the human eye.

See step S140, as shown in FIG. 2E, when the lens body 10 is immersed in the buffer solution 30, the first polymer and the second polymer of the first polymer film have different negative and positive charges on their chains, respectively. An ionic attractive force is generated between different types of charges, and a second polymer film can be formed on the surface of the first polymer film through the ion adsorption process, and as shown in FIG. Multiple layers of polymer of the first polymer film and the second polymer film with ionic attraction interspersed with each other.

In the present invention, by properly selecting the first polymer and the second polymer, a layer-by-layer deposition process of various polymers can be performed on the surface of the lens body. Among them, the first polymer has multiple negative charges in its entire chain, and the second polymer has multiple positive charges in its chain. In addition to the chemical bond formed between the first polymer layer and the lens body surface, this collection of opposite charges allows it to form multiple layers of polymers that are bonded to each other through an ion attraction process.

In addition, there are many possible options for performing the chemical conjugation and layer-by-layer deposition methods. Usually, the product to be reacted needs to be placed in a solvent containing reagents, and then, appropriate temperature and catalyst are provided. Starting conditions. In order to work in the contact lens industry, a storage tank filled with solvent and reactants is usually used, and the contact lens to be coated is immersed in the storage tank, and then, appropriate stirring and energy are provided to initiate the reaction.

Contact lenses are usually sold in small polypropylene containers, where the contact lenses are stored in an aqueous buffer solution. Reasons for this include storing contact lenses and preventing them from drying during transportation and storage, keeping the lens in the perfect shape for placement on the eyeball, and ensuring that the lens is comfortable to wear. Therefore, the key step in the production process of contact lenses is to fill the polypropylene container with a buffer solution, then put the lens in the solution, and then seal and autoclave it.

According to the method for preparing a contact lens with a polymer multilayer film disclosed in the present invention, all reactions can take place in a small container suitable for lens storage without the need to add additional basic equipment (such as a large reaction tank or storage tank for chemicals) , And can ensure all the reaction steps. Further, the lens body may be additionally stored in a first container, the first container is filled with a reaction solution, and the reaction solution contains the first polymer required to coat the first polymer film. The reaction solution may also contain a suitable catalyst for promoting the reaction. Then, the first container was sealed with aluminum foil. After that, the reaction mixture in the first container is supplied with energy in the form of ultraviolet light or temperature, and is appropriately stirred. This results in a reaction in the first container to apply the desired first polymer to the surface of the lens body to form a first polymer film.

Similarly, after the above reaction is completed, the lens body with the first polymer film on the surface can be transferred to a second container, the second container is filled with a buffer solution, and the buffer solution contains the second polymer for forming the first The second polymer film is above the first polymer film. Then, the second container is sealed and sterilized by moist heat to be sold to customers. Due to the presence of the required positive/negatively charged substances and the energy provided at high temperatures due to the sterilization process, multiple layers can be formed between the polymers on the surface of the contact lens. In practice, the first container and the second container may be polypropylene containers. The present invention utilizes the existing processes and equipment in the production process of contact lenses to ensure the execution of all reaction steps, thereby maximizing the benefits.

The present invention provides an example of a method for preparing a contact lens having a polymer multilayer film, which includes the following steps:

First, in step S100, 45 grams of hydroxyethyl methacrylate are weighed, and 1 gram of methacrylic acid (MAA) is added thereto. Thereafter, 0.75 g of 2-Hydroxy-2-methyl-1-phenyl-propan-1-one (Darocur™ 1173 from CibaTM) was added ) And 0.5 grams of ethylene glycol dimethacrylate (EGDMA) to obtain a monomer mixture for preparing the lens body. The monomer mixture was stirred at 35°C and 200 rpm for 50 minutes. After stirring, dopamine (1% v/v) was added to the monomers obtained in the previous step and stirred to ensure complete mixing. Then, the aforementioned monomer mixture was poured into a mold and cured at ambient temperature under ultraviolet light with a wavelength of 310-370 nm and light energy of 24-28 mW/cm ² for 35 minutes. After curing, the lens body was removed from the mold by being immersed in 20% ethanol at a temperature of 80°C for 20 minutes. Then, the lens body was placed in deionized water at 80°C for 55 minutes to wash the lens body to remove any unreacted chemicals.

Next, in step S110, 35 g of poly(vinyl alcohol) and 15 g of sodium alginate hydrophilic polymer are added to 1000 mL of water to prepare a reaction solution.

Thereafter, in step S120, the reaction solution prepared in step S110 is placed in a small polypropylene container, and the lens body prepared in step S100 is placed in the reaction solution. The polypropylene container was sealed, and then placed under a UV light source to allow UV light to pass through the transparent portion of the polypropylene container, and to reach the reaction solution when the inside of the container was in contact with the lens body, so that the polymer was cross-linked to the surface of the lens body. The total exposure time of the UV light source is 35 minutes.

Then, in step S130, 8.18 g of sodium chloride, 3.5 g of sodium phosphate dibasic dihydrate and 0.5 g of sodium dihydrogen phosphate dihydrate salt are added to 1000 mL of water to prepare a buffer Solution. At the same time, separate sodium alginate solutions (0.5% w/v in DDW) and sodium hyaluronate (2% w/v in DDW) were prepared in deionized water. The two solutions were stirred at a temperature of 45°C until a solute (sodium alginate Sodium hyaluronate). The two solutions are mixed in the buffer solution.

Step S140: Put the UV-cured lens body into 80° C. deionized water to wash away unreacted chemical substances. After washing, the lens body is placed in another polypropylene container, and the polypropylene container is filled with the buffer solution prepared in step S130. Then, the polypropylene container was sealed and placed in an autoclave, and subjected to moist heat sterilization at 121°C for 30 minutes. After completing this step, the contact lens can be safely worn on the eye.

In summary, according to the method for preparing a contact lens with a polymer multilayer film disclosed in the present invention, the polymer film is indeed attached to the surface of the lens body containing chemical groups by chemical conjugation, and further by different The ionic attraction between the negative charge and the positive charge of the polymer substance creates another polymer film to form a polymer multilayer film on the surface of the lens body that is well-bonded with two polymer films. When the contact lens is in contact with the eye, this polymer multilayer film can provide a smoother touch to the surface of the eye, and can also maintain good wettability of the contact lens surface. Therefore, the polymer multilayer film will cause the contact lens to be smoother and more comfortable than the ordinary contact lens without any coating.

In addition, the present invention can be realized by using the existing manufacturing process and production line of contact lenses, without the need to add additional basic equipment, which is beneficial to reduce costs and maximize benefits.

The above are only preferred embodiments of the present invention and are not intended to limit the scope of the present invention. Therefore, any changes or modifications based on the features and spirit described in the application scope of the present invention should be included in the patent application scope of the present invention.

Claims (7)

A method for preparing a contact lens with a polymer multilayer film includes the following steps: providing a lens body with a plurality of chemical groups on the surface of the lens body, the chemical groups being an amine group and a carboxyl group ) Or sulfone group; provide a reaction solution, add at least a first polymer to the reaction solution, the first polymer contains a negative charge; immerse the lens body in the reaction solution, under the action of a heat source , Making the first polymer chemically conjugated to the surface of the lens body to form a first polymer film; providing a buffer solution, adding at least a second polymer to the buffer solution, the second polymer contains a positive charge; And immersing the lens body in the buffer solution, an ionic attractive force is generated between the negative charge of the first polymer and the positive charge of the second polymer to form a second polymer film on the first through the ion adsorption process A polymer film surface, and a polymer multilayer film including the first polymer film and the second polymer film is formed on the surface of the lens body. The method for preparing a contact lens with a polymer multilayer film as described in claim 1, wherein the lens system comprises ethanolamine (Ethanolamine), dopamine (Dopamine), octadecylamine (Octadecylamine) or N, N- It is prepared by the monomer of N, N-Dimethylacrylamide. The method for preparing a contact lens with a polymer multilayer film according to claim 1, wherein the first polymer is selected from modified and unmodified polyethylene glycol (Polyethylene glycol), hyaluronic acid ( Hyaluronic acid), sodium hyaluronate, N-vinylpyrrolidone, polyvinyl alcohol (Poly(vinyl alcohol)), 2-methacryloyloxyethyl phosphorylcholine, poly(acrylamide), alginic acid and algae One or more of sodium alginate. The method for preparing a contact lens having a polymer multilayer film according to claim 1, wherein the second polymer is selected from hyaluronic acid, sodium hyaluronate, alginic acid, sodium alginate, modified and One or more of modified chitosan (Chitosan). The method for preparing a contact lens having a polymer multilayer film according to claim 1, wherein the reaction solution is contained in a first container, and after the step of immersing the lens body in the reaction solution, the first The container is sealed, and then the chemical conjugation process is performed under the action of the heat source. The method for preparing a contact lens having a polymer multilayer film according to claim 1, wherein the buffer solution is contained in a second container, and after the step of immersing the lens body in the buffer solution, the second The container is sealed and then sterilized by moist heat. The method for preparing a contact lens with a polymer multilayer film as described in claim 1, wherein the lens system uses lathe-cutting, cast-molding, spin casting or The combination of methods.

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