JPH04104220A - Method for hydrophilicity impartation to contact lens - Google Patents

Abstract

PURPOSE:To facilitate a safe and simple treatment and to improve the durability of a hydrophilic state after the treatment by immersing a contact lens into a specific soln., thereby forming a hydrophilicity impartation layer consisting of a crosslinked amino group-contg. polymer on the surface thereof. CONSTITUTION:The contact lens is immersed into a soln. contg. a water-soluble amino group-contg. polymer of the amt. effective at the time of the hydrophilicity impartation to the contact lens and a crosslinking agent of the amt. effective at the time of crosslinking this amino group-contg. polymer to form the hydrophicilicy impartation layer consisting of the crosslinked amino group-contg. polymer on the surface thereof. The water-soluble amino group- contg. polymer has a high hydrophilic property, is easily adsorptive on the contact lens and is safe. The examples of such polymer include protein, polysaccharides or the deriv. thereof, hydrophilic synthetic polymers, etc. The hydrophilic contact lens having the excellent resistance to physical impact, such as washing by rubbing by the hand and fingers is obtd. in this way by the simple operation.

Description

[Detailed Description of the Invention] (Technical Field) The present invention relates to a contact lens hydrophilic treatment method,
More specifically, the present invention relates to a method for advantageously hydrophilizing the surface of a contact lens having strong hydrophobicity, such as a hard contact lens or a non-hydrophobic soft contact lens.

(Background Art) Contact lenses currently in practical use can be roughly divided into water-containing materials and non-water-containing materials. Water-containing contact lenses mainly include polyhydroxymethacrylate and polyvinylpyrrolidone. Non-hydrophobic contact lenses include those whose main components are polymethyl methacrylate and silicone rubber, and copolymerized lenses with oxygen permeable polysiloxanyl methacrylate and methyl methacrylate. There are some that consist of combinations. While these water-containing contact lenses are comfortable to wear, they are easily contaminated with bacteria, and even if the cornea is damaged, they do not irritate the cornea, which can lead to serious diseases, making them highly dangerous. Although non-hydrocontaining contact lenses are relatively free from bacterial contamination, their surfaces are hydrophobic, and high oxygen permeability contact lenses have particularly strong hydrophobicity.

In contrast, biocompatible contact lenses molded from biocomponents such as collagen have also been proposed. In vertebrates, collagen makes up about 20 to 3 of the proteins in the whole body.
It is a fibrous protein that makes up 0% of the protein, and mainly functions as a supporting tissue and cell skeleton. This type of collagen has very weak antigenicity, is composed of hydrophilic amino acids, and has suitable conditions as a lens material, such as transparency, but when molded into lenses, it has physical It has inherent problems such as high strength, bacterial contamination, and difficulty in processing.

On the other hand, many methods have been proposed for modifying the surface of the highly hydrophobic and non-hydrophobic contact lenses to make them hydrophilic. Contact lenses with a hydrophilic surface, in other words, poor wettability with lachrymal fluid, can cause vision correction problems when worn, and poor movement of the lens on the cornea, leading to problems in fitting and wear. This is because there are problems such as giving people a foreign body sensation, and when such contact lenses are worn, lipids derived from eye oil etc. adhere to the lens surface and become dirty, causing the lens to deteriorate. This is because there is an inherent problem that cloudy symptoms appear and visibility becomes poor.

Therefore, methods using plasma treatment and chemical treatment with acids and alkalis have been considered as methods for making the surface of contact lenses, which are highly hydrophobic and non-hydrophobic, hydrophilic. There are problems with durability, and re-hydrophilization treatment requires considerable effort and expensive equipment.

Furthermore, in JP-A-63-271410, a contact lens is brought into contact with a solution containing a hydrophilic monomer and a photosensitizer selected from aromatic ketones or quinones, and a contact lens is irradiated with ultraviolet rays. A method for making lenses hydrophilic has been proposed.

However, this method has the problem that the hydrophilic monomer and ultraviolet rays are not safe for living organisms, and that the contact lenses themselves suffer from deterioration such as discoloration and deformation due to ultraviolet rays.

Furthermore, in U.S. Pat. No. 4,801,474, a plastic such as a contact lens is coated with an aqueous solution of mucopolysaccharide, dehydrated with a water-miscible solvent, then cross-linked and fixed with a polyisocyanate, and dried. A method has been proposed in which hydrophilicity is achieved during the process, but in addition to the complicated process, it is difficult to uniformly coat the mucopolysaccharide on the contact lens, and it is difficult to coat the mucopolysaccharide uniformly on the contact lens. Solvents have inherent problems such as adversely affecting lens specifications.

On the other hand, a relatively simple method of hydrophilic treatment is to immerse a contact lens in a solution containing a hydrophilic polymer and allow the polymer to adhere to the surface of the contact lens. A method of surface modification is also being considered.

As a solution containing such a hydrophilic polymer,
For example, Japanese Patent Publication No. 4B-37910 discloses a contact lens solution containing water-soluble polymers such as polyvinyl alcohol, hydroxyethyl cellulose, and polyvinylpyrrolidone. However, such treatment liquids have a weak adsorption power to the polymer contact lens surface, and are particularly difficult to use on highly hydrophobic materials such as non-hydrophobic contact lenses containing a large amount of silicone and fluorine components. It has the disadvantage of being ineffective.

Further, Japanese Patent Application Laid-open No. 63-246718 discloses a lens solution for surface treatment of contact lenses made of a polymer substance having an ionic charge. Since it is necessary to have a size of there were. Furthermore, even if contact lenses are treated with polymer solutions containing these ionic groups,
The durability is extremely poor, and even after contact lenses treated with such solutions are touched with one's fingers to put them on, or even after being put on the eye, the water wettability deteriorates after just a few blinks. It also has

Furthermore, U.S. Pat. No. 4,786,436 discloses a hydrophilic solution for contact lenses that utilizes the hydrophilic and biocompatible properties of collagen, and Japanese Patent Application Laid-Open No. 64-5001
Publication No. 4 proposes solutions for contact lenses containing cationic polymers such as cationic derivatives of polysaccharides such as chitosan, and by immersing contact lenses in these solutions, hydrophobic It is possible to make the surface of a contact lens hydrophilic, but in either case, the durability of the hydrophilic state is extremely poor, and contact lenses treated with such solutions cannot be touched with fingers or exposed to the eyes. Even after wearing it for a long time, it has the disadvantage that its wettability deteriorates after just a few blinks.

(Problem to be solved) The present invention has been made against the background of the above-mentioned circumstances, and the problem to be solved is to suppress or reduce stains such as lipids on contact lenses. In order to make such contact lenses comfortable to wear for long periods of time, there is a method for making the surface of the lens hydrophilic that is safer and easier to carry out, and that maintains the durability of the hydrophilic state after treatment. An object of the present invention is to provide a hydrophilic treatment method for contact lenses that has excellent properties.

(Solution Means) In order to solve this problem, the present invention crosslinks an effective amount of a water-soluble amino group-containing polymer to make a contact lens hydrophilic and a drooping amino group-containing polymer. A contact lens characterized in that a contact lens is immersed in a solution containing an effective amount of a crosslinking agent to form a hydrophilic layer made of the crosslinked amino group-containing polymer on the surface of the contact lens. The gist of this article is a method for making lenses hydrophilic.

Further, in the present invention, a contact lens is brought into contact with a solution containing an effective amount of a water-soluble amino group-containing polymer to make the contact lens hydrophilic, and the amino group-containing polymer is applied to the surface of the contact lens. After adsorption, contact with a solution containing an effective amount of crosslinking agent to crosslink the amino group-containing polymer crosslinks the amino group-containing polymer on the surface of the contact lens, thereby making the contact lens hydrophilic. The gist of the invention is also a method for making a contact lens hydrophilic, which is characterized by the following.

(Specific structure/effect) By the way, the water-soluble amino group-containing polymer used in the present invention has high hydrophilicity, easily adsorbs to contact lenses, and is safe. or derivatives thereof, hydrophilic synthetic polymers, and the like.

More specifically, examples of proteins include globular proteins such as albumin, globulin, and casein, and fibrous proteins such as collagen, keratin, and silk, and derivatives thereof; examples of such derivatives include partially hydrated proteins with an average molecular weight of 400 or more Examples include decomposition products and acylated products, and the origin thereof may be humans, animals such as cows and pigs, plants such as soybeans, etc. Among them, water-soluble collagen derivatives have good transparency, Since it has high biocompatibility and good adsorption to contact lenses, it is suitably used in the present invention.

As described above, water-soluble collagen derivatives useful in the present invention include, specifically, water-soluble collagen obtained by extracting insoluble collagen with acid, atelocollagen obtained by hydrolyzing and removing telopeptide, gelatin, and hydrolyzed collagen. Examples include collagen peptides and chemically modified methylated collagen decomposition products.

These water-soluble collagen derivatives can be prepared from tissues such as the skin dermis, bone, crotch, and lens capsule of mammals such as cows and pigs by known methods. For example, atelocollagen is a protein with a molecular weight of about 100,000 that is prepared by solubilizing insoluble collagen with pepsin, separating and purifying it with an acidic solution or sodium chloride.

Gelatin is prepared by pretreating insoluble collagen with acidic hot water or an alkali, and then extracting and purifying it with acidic hot water, as described in the Japanese Pharmacopoeia 11th Edition, Explanation. It is a protein with a molecular weight of 100,000 to 250,000. Hydrolyzed collagen is a peptide obtained by hydrolyzing atelocollagen or gelatin with a protease, etc., and its molecular weight varies depending on the decomposition conditions, but the hydrolyzed collagen used in the present invention has an average molecular weight of about 40.
It is 0 or more. Note that if the molecular weight of this water-soluble derivative of collagen is less than 400, the hydrophilic effect when brought into contact with a contact lens will be very small.

Furthermore, in the present invention, amino group-containing derivatives of polysaccharides are also suitably used as amino group-containing polymers, but as such amino group-containing derivatives of polysaccharides, any one that is water-soluble and has an amino group can be used. However, any one may be used. Specifically, there are deacetylated and desulfonated products of aminopolysaccharides, and derivatives to which amino groups are chemically added, and more specifically, dextran, cellulose, pullulan,
Starch, gum arabic, amino derivatives such as sodium alginate, such as diethylaminoethyl dextran, amino polysaccharide derivatives such as chitin, hyaluronic acid, chondroitin, chondroitin sulfate, keratan sulfate, ticuronic acid, colominic acid, deacetylated products, heparin, etc. Examples include desulfonated products of. Among them, deacetylated chitin is generally called chitosan.
It is easily available and has good biocompatibility, and is preferably used in the present invention. Also, its derivatives such as carboxylmethyl chitosan, glycol chitosan, N, N
-dimethylaminochitosan, N.

N-diethylaminochitosan and the like can also be used in the same manner.

Examples of hydrophilic synthetic polymers include polymers of amino acids such as lysine, arginine, and glycine, and polymers of hydrophilic monomers such as 2-hydroxymethacrylate and acrylamide with amino group-containing monomers such as aminoethyl acrylate and aminopropylacrylamide. Examples include copolymers.

Therefore, in the present invention, it is equally possible to use one type of these amino group-containing polymers or to use a mixture of two or more types.

Next, examples of crosslinking agents used in the present invention include polyfunctional compounds that crosslink amino groups and amino groups, transglutaminase, and condensation reagents that crosslink amino groups and carboxyl groups. Any one of them will be selected as appropriate.

Specifically, polyfunctional compounds include compounds that bond to two or more amino groups of an amino group-containing polymer at around room temperature, such as dialdehyde, isocyanate derivatives, bisdiazohenzidine, N, N' polymethylene, etc. Examples include biiodoacetamide, NN ethylene bismaleimide, halogen acetyl derivatives, polyepoxy compounds, and more specifically, glutaraldehyde, 0-phthalaldehyde, hexamethylene diisocyanate, toluene diisocyanate, hexamethylene dithiocyanate. Nat, N, N'
-bis(2-carboximidoethyl)tartaric acid imide dimethyl ester, N-(γ-maleimidobutyryloxy)succinimide, N,N'-(1,2-phenylene)bismaleimide, N,N'-(1,4 -phenylene) bismaleimide, chlorotriazine, ethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, glycerol polyglycidyl ether, sorbitol polyglycidyl ether, trimethylolpropane triglycidyl ether, and the like.

In the present invention, when the amino group-containing polymer has a carboxyl group in addition to an amino group, a condensation reagent that crosslinks the amino group and the carboxyl group may be used, for example, 1-ethyl-3 hydrochloride. -(3-dimethylaminopropyl)carbodiimide, 1-cyclohexyl-3
-(2-morpholyl-4-ethyl)-carbodiimide
Examples include metop-)luenesulfonate, N-ethyl-5-phenylisoxazolium-3'-sulfonate, and the like.

In addition, in the present invention, the amino base is a polymer,
When a protein derivative such as water-soluble collagen is used, it can also be crosslinked using transglutaminase. Transglutaminase is an enzyme that catalyzes the acyl transfer reaction between T-carboxyamide of glutamine residues in proteins and primary amines, and when the ε-amino group of lysine residues in proteins acts as an acyl acceptor, cross-linking occurs. A bond is formed. The origins of this enzyme include various organs such as the liver, crystalline lens, and epidermis of mammals, microorganisms such as bacteria and actinomycetes, and those produced by genetic manipulation. It can be of any origin.

Furthermore, in the present invention, a buffer, a functional group neutralizer, a metal chelating agent, a preservative, a thickener, etc. are appropriately added to the solution containing the amino group-containing polymer or crosslinking agent. It is also possible to do so.

Such buffering agents adjust the solution used in the present invention to a predetermined pH.
ophthalmologically acceptable buffers, such as phosphoric acid-based, boric acid-based, organic acid-based, carbonic acid-based, amino acid-based, ethanolamine-based, Tris buffer, heronal buffer, etc. can be used. In particular, buffers containing amino groups, such as amino acid buffers and Tris buffers, react with excess functional groups of the crosslinking agent and are therefore effective as functional group neutralizers. The buffer used is pH 2-12
For example, when atelocollagen, gelatin, etc. are used as amino group-containing polymers, acid-extracted collagen, chitosan, etc. are selected from the pH range of 4 to 9. When used, p) is selected from the range of 2 to 6, respectively.

The amount used is approximately 0.01 to 0.5 mol/
The concentration is selected to be E.

In addition, metal chelating agents are used to remove calcium, etc. in the tear fluid that adheres to contact lenses taken out of the eye.
It is added to prevent deposition on contact lenses, and specifically, ethylenediaminetetraacetic acid, nitrilotriacetic acid, salts thereof, and the like are preferably used. If the amount of such chelating agent is too small, the effect will not be sufficient, and if it is too large, no further effect will be obtained, so the amount used is about 0.0 O1 to 0.1 mol/l. It is desirable to adjust the content so that it is contained in a certain amount.

Furthermore, the preservative is used to prevent the solution used in the present invention from being contaminated with bacteria. Preservative,
Examples include methyl parahen, soluhinate, benzoic acid methyl ester, ethyl ester, propyl ester, etc., and are usually added in an amount of 0.001 to 1% (W/V).

Furthermore, the thickener makes it easier to clean when the excess solution adhering to the surface of the contact lens is finally washed away with fingers or the like when hydrophilizing the contact lens using the method according to the present invention. Specific examples include methylcellulose, carboxymethylcellulose, hydroxypropylcellulose, gum arabic, sodium chondroitin sulfate, sodium alginate, a copolymer of isobutylene and maleic anhydride, polyvinyl alcohol, etc. Usually 0.1-2% (W
/V).

In the present invention, the amino group-containing polymer as described above is adsorbed on the surface of a contact lens, and the amino group-containing polymers adsorbed on the contact lens surface are crosslinked with each other using a predetermined crosslinking agent, thereby forming a crosslinked amino group. Contact lenses are made hydrophilic by forming a hydrophilic layer made of polymers.
In the present invention, there is a method (method A) in which the amino group-containing polymer and the crosslinking agent are mixed in one liquid immediately before the hydrophilic treatment (method A), and a method in which the amino group-containing polymer is A contact lens is brought into contact with a solution containing the crosslinking agent to adsorb the amino group-containing polymer on the contact lens surface, and then the contact lens is brought into contact with a solution containing the crosslinking agent to absorb the amino group-containing polymer on the contact lens surface. A method (Method B) is adopted in which the contact lens is crosslinked to make the contact lens hydrophilic. In addition, such A
Method B has the advantage that the hydrophilic treatment can be carried out extremely easily because the adsorption and crosslinking reactions are carried out simultaneously in one container.
It also becomes possible to use a solution containing an amino group-containing polymer as a storage solution for contact lenses.

More specifically, in method A, first, a solution containing an amino group-containing polymer and a solution containing a crosslinking agent are mixed. There is no limit to the mixing volume ratio at this time, but the concentration of the amino group-containing polymer after mixing is about 0.
OOO1-5% (W/■), preferably about 0.1-2
% (W/V) and the crosslinking agent ranges from about 00OO1 to
1% (W/V), preferably about 0.01-0.5% (W
/V). Note that the ratio of both concentrations is not limited. When the concentrations of both are lower than this range, hydrophilization is not performed well,
On the other hand, if the concentration exceeds the above range, the crosslinking agent may react with the amino group-containing polymer in the solution, resulting in gelation of the solution. Further, the pH of the solution after mixing is used in a range of about 3 to 12.

Then, immediately after such mixing, the contact lens to be subjected to hydrophilic treatment is immersed in the solution,
Hydrophilization will be performed.

The hydrophilization is carried out at a temperature of about 5 to 40''C for about 5 minutes to 48 hours.

In this way? By immersing the contact lens in gH, the amino group-containing polymer is adsorbed onto the surface of the contact lens, and then the amino group-containing polymers are crosslinked with each other by a crosslinking agent, making them hydrophilic.

At this time, the crosslinking reaction proceeds immediately after mixing the amino group-containing polymer and the crosslinking agent, but since the adsorption of the amino group-containing polymer to the contact lens is significantly faster than the crosslinking reaction, hydrophilization is successfully achieved. It is thought that it will be done.

Finally, the hydrophilized contact lens is washed to remove excess solution adhering to the surface. As the cleaning agent used at this time, tap water, purified water, commercially available cleaning agents for contact lenses, preservatives, etc. can be used. As a cleaning method, any method such as rinsing with running water or rubbing with fingers can be adopted, and the hydrophilicity of the contact lens does not change by these methods.

On the other hand, in method B, first, a solution containing an amino group-containing polymer is brought into contact with a contact lens to be subjected to a hydrophilic treatment. Here, the amount of the amino group-containing polymer to be used is such that when the amino group-containing polymer is brought into contact with the contact lens, the amino group-containing polymer will be adsorbed to the contact lens and the water wettability of the lens surface will be good. Good, specifically about 0.0001 to 20 (W
/V)%, preferably in the range of 0.01 to 2 (W/V)%. Note that the amount of the amino group-containing polymer used is about 0. If OOO is less than 1%, the hydrophilic effect upon contact with a contact lens will be very small, and if it is more than about 20%, the hydrophilic effect will not be improved.

Further, the pH of the solution containing the amino group-containing polymer can be appropriately selected within a wide range of approximately pH 3 to 12, depending on the properties of the polymer.

Further, the contact lens may be contacted with the solution containing the amino group-containing polymer at a temperature of 5 to 40° C. for about 5 seconds or more.

A specific method for bringing the contact lens into contact with the solution containing the amino group-containing polymer is to fix the contact lens with a holder or the like, and place it in a container filled with the solution containing the amino group-containing polymer. Any method may be employed, such as a method of dipping or a method of dropping a solution containing the amino group-containing polymer onto the surface of the contact lens using a dropper or the like.

Excess amino group-containing polymer adhering to the contact lens surface is then washed away with an aqueous medium. Such an aqueous medium must not contain anything that would interfere with the adsorption of the amino group-containing polymer and contact lenses;
Specifically, water such as tap water, purified water, saline, contact lens storage solution, etc. can be mentioned, but usually tap water is used because it can be easily used in large quantities. This rinsing operation involves immersing the treated contact lens in a container filled with water for several seconds or more, or exposing the treated contact lens in running water to remove excess amino acids. This can be done by washing away the group-containing polymer.

As a result, the amino group-containing polymer is adsorbed to the contact lens, which has a hydrophobic surface, resulting in good water wettability.
If this continues, if your fingers, lens holder, etc. touch the lens surface, the amino group-containing polymer will come off.
This will reduce the water wettability of the lens surface.

Therefore, next, in order to crosslink the adsorbed amino group-containing polymer and form a film that cannot be removed by physical force such as hand washing, a solution containing the amino group-containing polymer and the above treatment are combined. The applied contact lens is brought into contact with the applied contact lens. The conditions for this contact are approximately 5 to 40"
at a temperature of 5 minutes to 48 hours, preferably 20 minutes to 18 hours.
The method of contact is to fix the contact lens with a holder etc. and immerse it in a container filled with a solution containing a cross-linking agent, or to apply a solution containing a cross-linking agent to the contact lens using a dropper etc. Any method may be employed, such as a method of dropping it onto the surface.

The amount of such crosslinking agent used is approximately 0.001 to 5% (
W/V), preferably in the range of about 0.01 to 1% (W/V). Note that if the amount used is less than about 0.001%, the amino group-containing polymer will not be crosslinked sufficiently, and if it is more than about 5%, the hydrophilic effect will not be improved.

Further, the pH of the solution containing the crosslinking agent is appropriately selected within the range of about 3 to 12, depending on the type of crosslinking agent. For example, when using glutaraldehyde as a crosslinking agent, it is used at a pH of about 6 to 12, preferably at a pH of about 7 to 9, and when using a carbodiimide as a crosslinking agent, it is used at a pH of about 3 to 7, preferably at a pH of about 7 to 9. It is used in the range of about 4-6.

Finally, the hydrophilized contact lens is washed to remove excess crosslinking agent adhering to the surface. As the cleaning agent used at this time, in addition to tap water and purified water, commercially available contact lens cleaning agents and storage solutions may be used. Any method of cleaning can be used, such as rinsing with running water or rubbing with fingers, and such methods do not change the hydrophilicity of the contact lens.

Furthermore, if there is a possibility that the functional groups of the crosslinking agent remain even after the above-mentioned washing, immersion in a solution containing amino groups can be performed as necessary. In this case, as the solution containing amino groups, any solution of amino acids, tris(hydroxy)aminomethane, amines, etc. can be used; You may do so.

As described above, the hydrophilic treatment methods (method A and method B) according to the present invention
By using the method (method), hydrophilization that is resistant to physical shocks such as hand washing can be carried out safely and extremely easily, and contact lenses that have been subjected to such hydrophilization can be
Even when worn for long periods of time, dirt such as lipids does not adhere or stick, making it comfortable to wear.

(Examples) Below, some examples of the present invention will be shown to clarify the present invention more specifically. By the description,
Needless to say, it is not subject to any restrictions.

Example 1 Tris(trimethylsiloxy)silylpropyl methacrylate and 1.1. A non-water-containing contact lens made of a copolymer mainly composed of L3,3.3-hexafluoro-2-propyl methacrylate is prepared, and the contact angle of this lens is measured using a contact angle meter (Elma Optical) according to the droplet method. ■Made in
When measured using a goniometer type contact angle meter (Model G-1), it was 99.6 degrees.

Next, this contact lens was coated with 0.1% gelatin (
Difco Laboratories) and 0.
20mM phosphate buffer containing 5% glutaraldehyde (
pH 7.0) at room temperature for 2 hours, and then
A hydrophilic treatment was performed by washing with hands and fingers using a contact lens cleaning solution [manufactured by @Menicon, trade name: Nio-2 Care] and rinsing thoroughly with tap water. The contact angle of the thus obtained hydrophilic treated contact lens was measured in the same manner as above and found to be 43.8 degrees.

Comparative Example 1 Using the same contact lens as in Example 1, this was
．． 20mM phosphate buffer (pH 7,
0) at room temperature for 2 hours. Thereafter, the lenses were washed with hands and fingers using a contact lens cleaning solution (trade name: Nio-2 Care, manufactured by Menicon), and thoroughly rinsed with tap water to complete the hydrophilic treatment. The contact angle of the thus obtained lens was measured in the same manner as above and was found to be 93.8 degrees.

From the results of Example 1 and Comparative Example 1, it is recognized that according to the present invention, an extremely high hydrophilic effect can be obtained.

Example 2 The same operation as in Example 1 was carried out using a non-hydrous contact lens made of a copolymer of methyldi(trimethylsiloxy)silyl(propylglycerol) monomethacrylate and methyl methacrylate in place of the contact lens in Example 1. I did this. As a result, the contact angle before the hydrophilic treatment was 101.6 degrees, while the contact angle after the hydrophilic treatment was 52.0 degrees.

Example 3 Instead of the hydrophilic solution of Example 1, 20 mM phosphate buffer (p
When the same operation as in Example 1 was performed using H6,5), the contact angle after the hydrophilic treatment of the lens was 54.9 degrees.

Example 4 In place of the hydrophilic solution of Example 1, a 20 mM phosphate buffer (pH 7.0) containing 1% raw serum albumin (manufactured by Wako Pure Chemical Industries, Ltd.) and 0.1% glutaraldehyde was used, When the same operation as in 1 was performed, the contact angle after the hydrophilic treatment of the lens was 61.8 degrees.

Example 5 Instead of the hydrophilic solution of Example 1, 0.1% chitosan [
manufactured by Koyo Chemical ■] and 0.2% 1-ethyl hydrochloride (3
Hydrophilic treatment was carried out in the same manner as in Example 1 using a dilute hydrochloric acid solution (pH 4.0) containing (dimethylaminopropyl) carbodiimide, and the contact lens cleaning solution [■Menicon, trade name: Nio-2 Care] was applied 10 times. ], and after rinsing thoroughly with tap water, the contact angle was measured in the same manner as above and found to be 63.8 degrees.

Comparative Example 2 Instead of the hydrophilic solution of Example 1, 0.1% chitosan [
Hydrophilic treatment was performed in the same manner as in Example 1 using a dilute hydrochloric acid solution (pH 4.0>, manufactured by Koyo Chemical), and a contact lens cleaning solution (manufactured by Menicon, trade name: Nio-2 Care) was applied 10 times. After washing with hands and fingers and rinsing well with tap water, the contact angle was measured in the same manner as above and found to be IO2.2 degrees.

From the results of Example 5 and Comparative Example 2, it is clear that the hydrophilic effect of the present invention is extremely high.

Example 6 Instead of the hydrophilic solution of Example 1, 0.1% gelatin,
20mM Tris buffer (pH 6,8) containing 0.05% glutaraldehyde, 0.02% trilium acetate ethylenediaminetetraacetate, 0.15% potassium sorbate, 0.2% carboxymethylcellulose C manufactured by Wako Pure Chemical Industries, Ltd. When the same operation as in Example 1 was performed using the lens, the contact angle of the lens after the hydrophilic treatment was 56.9 degrees.

Example 7 A contact lens similar to Example 1 was prepared, and this contact lens was mixed with 1% gelatin, 0.02% trilium acetate ethylenediaminetetraacetate, 0.15% potassium sorbate, and 0.2% carboxymethyl cellulose. including 20
(mM) Lys buffer (pH 6,8) for 30 seconds.

Next, this contact lens was lightly rinsed with tap water, and then immersed in 50 mM sodium bicarbonate (pH 8.0) containing 0.1% glutaraldehyde for 30 minutes. After that, wash this contact lens with contact lens cleaning solution [
■Nio-2 Care manufactured by Menicon] was washed with hands and fingers, and after rinsing thoroughly with tap water, the contact angle was measured in the same manner as in Example 1 and found to be 55.1 degrees. Ta.

Example 8 Instead of the hydrophilic solution (buffer) of Example 7, 0.1%
Collagen [-Maru Falcos ■, product name: Core Bra]
Using 20mM citrate buffer (pH 4, O) containing
When the same operation as in Example 7 was performed, the contact angle of the lens after the hydrophilic treatment was 56.8 degrees.

Example 9 Instead of glutaraldehyde in Example 7, trimethylolpropane triglycidyl ether [manufactured by Kyoeisha Yushi Kagaku Kogyo ■, trade name: Epolite 100MF] was used, and 1
Example 7 except that the immersion treatment was carried out at room temperature for 8 hours.
When the hydrophilic treatment was carried out in the same manner as above, the contact angle of the lens after the hydrophilic treatment was 66.5 degrees.

(Effects of the Invention) As is clear from the above description, according to the present invention, a water-soluble amino group-containing polymer is adsorbed onto the surface of a contact lens to be made hydrophilic, and at the same time, the amino group-containing polymer is By crosslinking group-containing polymers to form a hydrophilic layer made of the crosslinked amino group-containing polymer on the surface of the contact lens, and by making the hydrophilic layer hydrophilic, it is easy to operate without the need for expensive equipment. This makes it possible to make contact lenses hydrophilic that have excellent durability against physical impacts such as rubbing with fingers.

Claims (6)

[Claims] (1) Immersing a contact lens in a solution containing an effective amount of a water-soluble amino group-containing polymer to make the contact lens hydrophilic and an effective amount of a crosslinking agent to crosslink the amino group-containing polymer. A method for making a contact lens hydrophilic, comprising: forming a hydrophilic layer made of the crosslinked amino group-containing polymer on the surface of the contact lens. (2) Bringing a contact lens into contact with a solution containing an effective amount of a water-soluble amino group-containing polymer to make the contact lens hydrophilic, and adsorbing the amino group-containing polymer onto the surface of the contact lens; A contact characterized in that the amino group-containing polymer on the surface of the contact lens is crosslinked by contacting with a solution containing an effective amount of a crosslinking agent to crosslink the amino group-containing polymer, thereby making the contact lens hydrophilic. How to make lenses hydrophilic. (3) The method for making a contact lens hydrophilic according to claim 1 or 2, wherein the amino group-containing polymer is water-soluble collagen or a derivative thereof. (4) The method for making a contact lens hydrophilic according to claim (1) or (2), wherein the amino group-containing polymer is a polysaccharide derivative. (5) The method for making a contact lens hydrophilic according to claim 1 or 2, wherein the crosslinking agent is a polyfunctional compound that undergoes a crosslinking reaction with two or more amino groups. (6) Claim (1) wherein the amino group-containing polymer has a carboxyl group in addition to the amino group, and the crosslinking agent is a condensation reagent that crosslinks the amino group and the carboxyl group.
Or the method for making contact lenses hydrophilic as described in (2).