KR20070022027A - Ocular lens material and method for producing same - Google Patents

Abstract

The present invention is an ocular lens material characterized in that a phosphorylcholine group having a specific structure is covalently bonded to an ophthalmic lens material surface by a post-treatment in which a phosphorylcholine group-containing compound is reacted with an ocular lens material. An object of the present invention is to provide a contact lens for preventing protein adsorption and a method of manufacturing the same.

Phosphorylcholine, eye, lens, protein adsorption

Description

Eye lens material and its manufacturing method {OCULAR LENS MATERIAL AND METHOD FOR PRODUCING SAME}

The present invention relates to an eye lens material such as a contact lens, a method for producing the same, and a method for preventing protein adsorption. More specifically, the present invention relates to a method of treating ocular lens material surfaces (particularly contact lenses) by post-treatment of novel phosphorylcholine group-containing compounds to prevent contamination by proteins.

It is known to superpose | polymerize a phosphoryl choline group containing monomer and to use for a contact lens material (patent documents 1-3). For example, Patent Document 1 discloses a water-soluble soft contact lens containing a phosphorylcholine group-containing (meth) acrylic acid ester as a constitutional unit, excellent in water content, oxygen permeability, tensile strength, and a small amount of protein adsorption. It is described that the adhesion of contaminants can be suppressed.

Further, as a post-treatment method of a contact lens, Patent Document 4 describes that a contact lens having a hydrophilic surface by polymerizing a phosphorylcholine group-containing monomer on the contact lens surface and producing a contact lens with little protein adsorption is described.

Patent Document 5 also discloses a method of chemically bonding a low molecular weight phosphorylcholine compound to a contact lens surface to reduce adsorption of proteins. In this method, however, when the follow-up is actually performed, the phosphorylcholine group cannot be sufficiently introduced into the contact lens surface. In other words, the essential difference between the present invention and the method disclosed in Patent Document 5 is the difference in the efficiency of introduction of the phosphorylcholine group into the contact lens surface, thereby producing an excellent effect of more effectively inhibiting protein adsorption. Moreover, the material of a contact lens can be used unevenly, and also the effect of adsorption prevention by the structure (especially -NH-) peculiar to this invention can also be expected.

On the other hand, contamination of contact lenses results in adsorption of proteins and lipids contained in tears into contaminants, and there is a risk of causing eye disorders such as allergies and infectious diseases by the contaminants (Non Patent Literature 1). In particular, a water-containing soft contact lens mainly composed of a polymer of 2-hydroxyethyl methacrylate, a high-function soft contact lens copolymerized with a small amount of methacrylic acid as an ionic monomer, or N-vinylpi as a hydrophilic monomer. In soft contact lenses containing a polymer of rolidone or N, N-dimethylacrylamide as a main component, contaminants caused by proteins become a fatal problem.

Patent Document 1: Japanese Patent Application Laid-Open No. 10-177152

Patent Document 2: Japanese Patent Application Laid-Open No. 2000-111847

Patent Document 3: Japanese Patent Application Laid-Open No. 2000-169526

Patent Document 4: Japanese Patent Application Laid-Open No. 2001-337298

Patent Document 5: Japanese Patent Application Laid-Open No. 5-505121

[Non-Patent Document 1] "Contamination of Soft Contact Lenses and Their Analysis", Material Stage, Vo1.4, No. 1, 2004

Problems to be Solved by the Invention

The present invention provides a contact lens in which a phosphorylcholine group having a specific structure is directly covalently bonded to a contact lens surface by post-treatment to inhibit protein adsorption of the contact lens, thereby preventing contamination by protein.

That is, the present invention does not produce a protein adsorption preventing contact lens by polymerizing a monomer containing a phosphorylcholine group, as in the method described in Patent Documents 1 to 3 above, but prevents excellent protein adsorption by post-treatment to the contact lens. It is intended to have a function.

In addition, the present invention does not introduce a phosphorylcholine group by polymerizing a phosphorylcholine group-containing monomer on the surface of a contact lens and coating it with another polymer different from the contact lens, as in the method described in Patent Document 4. It is an object to introduce a direct phosphorylcholine group irrespective of a coating | cover, and it aims at exhibiting the outstanding protein adsorption prevention effect which is excellent in durability, and does not change the intrinsic property of a contact lens with a polymer coating.

In addition, in the processing method of patent document 5, although the synthesis method of the phosphorylcholine group containing compound which has a carboxyl group for processing a raw material is not described, when synthesize | combining based on common sense of normal organic chemistry, the method is Extremely troublesome and difficult, multi-stage yields are low, and the reaction of introduction of the phosphorylcholine compound having a hydroxyl group on the contact lens surface also does not proceed sufficiently under the conditions described, and the introduction amount is low. Although it is insufficient in order, it is possible to introduce a sufficient amount of phosphorylcholine by the method of the present invention and to exert an excellent protein adsorption preventing effect.

Means to solve the problem

That is, the present invention provides an ophthalmic lens material characterized in that the phosphorylcholine group is covalently bonded to the material surface by a post-treatment in which the phosphorylcholine group-containing compound represented by the following formula (1) is reacted with the ocular lens material. To provide.

In formula, m is 2-6 and n is 1-4. In addition, -O- may be sufficient as -NH- of Formula (6). X ₁ , X ₂ and X ₃ are each independently a methoxy group, an ethoxy group or a halogen. However, up to two of X <_1> , X <_2> and X <_{3> may be} any of a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, and an isobutyl group.

R is either of the structures in the following formulas (2) to (4), except that the compound of formula (1) is represented by A-R-B in the following formulas (2) to (4).

In Formulas (2) to (4), L represents 1 to 6 and P represents 0 to 3.

In addition, the present invention is covalently bonded to the surface of the eye lens material by the phosphoryl choline group by post-treatment by reacting the phosphoryl choline group-containing compound represented by the following formula (5) and / or (6) to the eye lens material An ophthalmic lens material is provided.

In formula, m is 2-6 and n is 1-4. In addition, -O- may be sufficient as -NH- of Formula (6). X ₁ , X ₂ and X ₃ are each independently a methoxy group, an ethoxy group or a halogen. However, up to two of X <_1> , X <_2> and X <_{3> may be} any of a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, and an isobutyl group.

Moreover, this invention provides the said ocular lens material characterized by containing the monomer which has a hydroxyl group in the monomer which comprises an ocular lens material.

Moreover, this invention provides the said ocular lens material characterized by containing the monomer which has a carboxyl group in the monomer which comprises an ocular lens material.

Moreover, this invention provides the said eye lens material characterized by containing 2-hydroxyethyl methacrylate in the monomer which comprises an eye lens material.

Moreover, this invention provides the said ocular lens material characterized by containing vinyl alcohol in the monomer which comprises an ocular lens material.

Moreover, this invention provides the said eye lens material characterized by containing (meth) acrylic acid or (meth) acrylic acid ester in the monomer which comprises the eye lens material.

Moreover, this invention provides the said ocular lens material characterized by containing N-vinylpyrrolidone in the monomer which comprises an ocular lens material.

The present invention also provides a method for producing an ophthalmic lens material, wherein the phosphorylcholine group is covalently bonded to the ophthalmic lens material surface by a post-treatment wherein the phosphorylcholine group-containing compound is reacted with the ocular lens material. To provide.

In addition, the present invention covalently bonds a phosphorylcholine group to the ophthalmic lens material surface by post-treatment of reacting the phosphorylcholine group-containing compound with the ocular lens material to prevent adsorption of proteins to the ocular lens material. It is to provide a method for preventing protein adsorption of an eye lens material, characterized in that.

Effects of the Invention

Since the contact lens, which is an ophthalmic lens material of the present invention, directly covalently bonds a phosphorylcholine group to the contact lens surface, it effectively suppresses protein adsorption of the contact lens and exhibits an excellent antifouling effect. In addition, the wearability can be improved by improving water retention.

In addition, since the protein adsorption prevention function can be provided by post-treatment, the present invention can be easily used for existing contact lenses.

Since the phosphorylcholine group is not introduced by the polymer coating, the phosphorylcholine group can be introduced into contact lenses of all materials, and the durability is excellent, and the original properties of the contact lens are not deteriorated.

The contact lens obtained by the present invention is a contact lens excellent in wearing comfort. Therefore, it can use suitably for the contact lens which is easy to feel a foreign material because of the inferior flexibility of a material.

The present invention is not limited to the material of the contact lens at all, and can be used in a post-treatment method, which has the advantage that a contact lens having a covalently bonded phosphorylcholine group of a specific structure can be produced. The post-treatment can be preferably performed in an organic solvent in a hydrous organic solvent, and has the advantage that it does not need to be performed with exact anhydrous conditioning. In addition, the adsorption prevention effect by the unique structure (especially -NH-) of Formula (1) can also be anticipated.

1 is a 1H-NMR spectrum of the compound of formula (9).

2 is a 1 H-NMR spectrum of the compound of formula (10).

3 is a graph of protein adsorption amounts for contact lenses of Examples and Comparative Examples.

Best Mode for Carrying Out the Invention

The present invention will be described in detail below.

`` Eye Lens Material ''

In the present invention, the eye lens material is a molded product of a material to be mounted in the eye. Primarily contact lenses.

A contact lens of any material may be used. For example, methacrylic acid (MAA), acrylic acid (AA), 2-hydroxyethyl methacrylate (HEMA), N-vinylpyrrolidone (NVP), N, N-dimethylacrylamide (DMAA), vinyl Alcohol (VA), methyl methacrylate (MMA), trifluoroethyl methacrylate (TFEMA), cellulose acetate butyrate (CAB), fluorosilicone, hexafluoroisopropyl methacrylate, perfluoroalkyl methacrylate Polymers such as latex, siloxaneyl methacrylate (SiMA), siloxaneyl styrene (SiSt), ethylene glycol dimethacrylate (EGDMA), allyl methacrylate (AMA), silicone macromers or copolymers of two or more monomers It is possible to manufacture the contact lens of the present invention from a contact lens composed of a contact lens. Regardless of the kind of monomer, this invention can be used also for both a hard contact lens and a soft contact lens.

As a monomer constituting the contact lens, a soft contact lens composed mainly of 2-hydroxyethyl methacrylate and an ionic soft contact lens copolymerized with methacrylic acid are typical soft contact lenses, and proteins are easily adsorbed. . Therefore, it is preferably treated by the method of the present invention.

Moreover, as a monomer which comprises a contact lens, the contact lens which has a vinyl alcohol or N-vinylpyrrolidone as a main component or a copolymerization component is also processed suitably by the method of this invention.

Moreover, as a monomer which comprises a contact lens, the hard contact lens which has a methyl (meth) acrylate as a main component, especially the oxygen-permeable or the continuous wear hard contact lens which a protein adsorb | sucks are also processed suitably by the method of this invention.

As a functional group which the said phosphorylcholine group of said Formula (1) can covalently bond, the contact lens containing 2-hydroxyethyl methacrylate and a polyvinyl alcohol polymer has a hydroxyl group, and it is preferable.

However, even without these functional groups, it is possible to introduce a hydroxyl group covalently bonded to the contact lens surface by plasma treatment. For example, a contact lens made of an N-vinylpyrrolidone polymer can introduce a hydroxyl group by plasma treatment to produce the contact lens of the present invention.

"Method of manufacturing lens material for eyeball"

The phosphorylcholine group-containing compound of formula (1) or (5) or (6) is bonded to the surface of the hydroxyl group on the contact lens surface of the ophthalmic lens material by covalent bonding.

The hydroxyl group to be covalently bonded is a hydroxyl group of a contact lens constituent monomer, or a hydroxyl group newly introduced into the contact lens surface later by plasma treatment or the like.

Thereby, the phosphorylcholine group is directly covalently bonded to the contact lens surface by post-treatment.

Reaction of the hydroxyl group of a contact lens with the said phosphorylcholine group containing compound forms a covalent bond by dehydration reaction according to a conventional method. The phosphorylcholine group-containing compound described above may be covalently bonded to any functional group that is present or introduced into the contact lens surface, without being limited to a hydroxyl group.

The phosphorylcholine group-containing compound represented by the formula (1) or (5) or (6) is a novel compound having a phosphorylcholine group and capable of covalently bonding to a functional group on the contact lens surface as a silane coupling agent.

"The manufacturing method of the phosphoryl choline group containing compound of Formula (1) or (5) or (6)"

It can manufacture by the following method.

The phosphorylcholine derivative represented by the following formula (7) is dissolved in distilled water. The phosphorylcholine derivatives of the following formula (7) are known compounds and commercially available products can be obtained.

The aqueous solution of the compound of formula (7) is cooled in an ice-water bath, sodium periodate is added and stirred for 5 hours. The reaction solution is concentrated under reduced pressure, dried under reduced pressure, and the phosphorylcholine derivative having an aldehyde group represented by the following formula (8) is extracted with methanol.

Next, 0.5 equivalent of 3-aminopropyl trimethoxysilane is added to the methanol solution of formula (8). After stirring this mixed solution at room temperature for a predetermined time, ice-cooling is carried out, an appropriate amount of sodium cyanohydroborate is added, it returns to room temperature, and it stirred for 16 hours. During this time, dry nitrogen continues to flow into the reaction vessel. After filtering out the precipitate, a methanol solution of formula (5) is obtained.

In this method, the compound of the following formula (9) is obtained as the compound of the formula (5). By the same method, the compound of Formula (1) or Formula (5) of General Formula is obtained using another silane compound instead of 3-aminopropyltrimethoxysilane.

Furthermore, the aqueous solution of the compound of formula (7) is cooled in an ice-water bath, sodium periodate and a catalytic amount of ruthenium trichloride are added and stirred for 3 hours. The reaction solution is concentrated under reduced pressure, dried under reduced pressure, and the phosphorylcholine derivative (a) having a carboxyl group represented by the following formula is extracted with methanol.

Next, 1.2 equivalents of thionyl chloride are added to the acetonitrile or N, N-dimethylformamide dispersion of formula (a), and 0.9 equivalent of 3-aminopropyl trimethoxysilane is added to the solution stirred for 30 minutes. This mixed solution is stirred at room temperature for 4 hours.

In this method, the compound of the following formula (10) is obtained as the compound of the formula (6). By the same method, the compound of Formula (1) or Formula (5) of General Formula is obtained using another silane compound instead of 3-aminopropyl trimethoxysilane.

In addition to the thionyl chloride, the reagent used in the condensation reaction can be used without any problem so long as it generally produces carboxylic acid halides such as phosphorus pentachloride, phosphorus oxychloride, phosphorus tribromide, and oxalyl chloride.

The compounds of formulas (9) and (10) can be purified by the following method. That is, the methanol solution obtained above is concentrated under reduced pressure, and this residue is used as a sample. The capsules AQC18 (size: 4.6 mm id × 250 mm) (Shiseido Co., Ltd.), a column for high performance liquid chromatography, were connected to an HPLC apparatus, and methanol was flowed at a flow rate of 1 mL / min to equilibrate, and then the sample was Inject 10 μL. By using a differential refractometer as a detector, a chromatogram can be obtained, and the compound of formula (9) or (10) can be isolated.

However, the compound can be used as it is in the step of the methanol solution before purification.

Said procedure can be performed similarly even if m and n in the compound shown by Formula (5) or (6) change. The procedure shown here is the case where m = 3 and n = 2. Further, by using 3- (2-aminoethylaminopropyl) trimethoxysilane or the like as the silane compound having an amino group, it is also possible to insert a secondary amine between the silane moiety and the phosphorylcholine group. The same procedure can be performed. The reaction solvent is not particularly limited in the case of the formula (5), and in addition to the above-mentioned methanol, water, alcohols such as ethanol, propanol, butanol, aprotic solvents such as N, N-dimethylformamide or dimethyl sulfoxide can be used. Can be. However, in order to prevent superposition | polymerization of the organosilane compound in reaction, a dehydration solvent is preferable. In the case of formula (6), an aprotic solvent is preferably used in order to prevent decomposition of the produced acid chloride.

When the methoxy group (OCH ₃ ) in the formula (5) or (6) is an ethoxy group (OC ₂ H ₅ ), the reaction is carried out by converting methanol into ethanol, and in case of Cl, dimethylformamide or dimethyl sulfoxide. Change it.

Moreover, when 2 or 1 of the methoxy group, ethoxy group, or Cl which couple | bond with Si is substituted by any of methyl group, ethyl group, propyl group, isopropyl group, butyl group, and isobutyl group, it is the same as said method. Can be manufactured.

`` How to introduce phosphorylcholine groups into hydroxyl groups of contact lenses ''

Covalent bonds are formed by dehydration from the hydroxyl groups on the contact lens surface and Si-OMe of the compounds of the following formulas (9) and / or (10). This chemical reaction proceeds quantitatively very easily in most organic solvents. This dehydration reaction is preferable because it can introduce a chemically and physically stable phosphorylcholine group.

Specifically, commercially available contact lenses are used in organic solvents such as methanol, ethanol, N, N-dimethylformamide and dimethyl sulfoxide in which the phosphorylcholine group-containing compound of formulas (9) and / or (10) is dissolved. It was immersed and reacted at room temperature. As reaction conditions, you may heat as needed, and water, an acid, a base catalyst, etc. can also be added.

In formula, OMe may be OEt and Cl. The methyl group, ethyl group, propyl group, isopropyl group, butyl group, and isobutyl group may be up to two of OMe or OEt or Cl bonded with Si.

The phosphorylcholine group of formula (1) introduced by the above method or the like is quantified by quantitative analysis of phosphorus by the molybdenum blue method after pretreatment using perchloric acid (Reference: Experimental Chemistry Lecture 14). 4th edition analysis, Maruzen, 3.8.2).

In addition, the amount of phosphorylcholine group introduced into the contact lens is preferably 0.0001 µmol / mg or more. If it is less than 0.0001 µmol / mg, sufficient protein adsorption inhibitory effect may not be obtained, but this is not the case when phosphorylcholine groups are introduced only on the surface of the contact lens. On the other hand, since the effect of inhibiting protein adsorption is increased in a portion having a large amount of introduction, the amount of introduction is not particularly limited.

Next, the present invention will be described in more detail based on Examples. In addition, this invention is not limited to these Examples.

`` Protein adsorption experiment ''

The contact lenses of the present invention were produced using commercially available contact lenses. The adsorption inhibition effect of proteins was compared by the following evaluation method.

"Assessment Methods"

The contact lens was immersed in 3 ml of artificial tear fluid and left at 37 ° C. for 24 hours. The amount of protein in the solution portion was quantified by the BCA method (calibration line Albumin Bovine), and the amount of protein reduction in the solution portion was calculated as the amount of protein adsorption.

Artificial tear liquid was obtained by dissolving the following components in ultrapure water.

Lysozyme 1.20 mg / ml, Albumin 3.88 mg / ml, γ-globulin 1.61 mg / ml, sodium chloride 9.00 mg / ml, potassium dihydrogen phosphate 0.14 mg / ml, disodium hydrogen phosphate heptahydrate 0.80 mg / ml

(Reference) FDA Guideline Draft: Testing guidelines for class III soft (hydrophilic) contact lens solution, lens group compatibility test, July 15, 1985.

Synthesis Example 1 Production of Compound of Formula (9) (Production of Amine Type Silane Coupler Containing Phosphoryl Choline Group)

1-α-glycerophosphorylcholine (450 mg) was dissolved in 15 ml of distilled water and cooled in an ice water bath. Sodium periodate (750 mg) was added and stirred for 5 hours. The reaction solution was concentrated under reduced pressure, dried under reduced pressure, and the target product shown in Chemical Formula (5) was extracted with methanol. Subsequently, after 3-aminopropyl trimethoxysilane (300 mg) is added to the said methanol solution, after stirring at room temperature for 5 hours, it is ice-cooled, sodium cyanohydroboride (100 mg) is added, and room temperature Return to the mixture and stir for 16 hours. During this time, dry nitrogen continues to flow into the reaction vessel. After filtering out the precipitate, a methanol solution of formula (9) is obtained.

1H-NMR data of the compound of formula (9) is shown.

Synthesis Example 2 Production of Compound of Formula (10) (Production of Amide Silane Coupler Having Phosphoryl Choline Group)

5 g of 1-α-glycerophosphorylcholine were dissolved in 30 ml of 70 ml-acetonitrile of water. Under ice-cooling, 17 g of sodium periodate and 80 mg of ruthenium trichloride were added, and the mixture was stirred overnight. The precipitate was filtered, concentrated under reduced pressure, and carboxymethylphosphorylcholine as the target represented by the formula (6) was obtained by methanol extraction. Subsequently, 3 g of the compound of formula (6) and thionyl chloride were added to acetonitrile under ice cooling, stirred for 30 minutes, 3.8 g of 3-aminopropyl trimethoxysilane was added, and dry nitrogen was added to the reaction vessel. Then, it poured and stirred at room temperature for 3 hours, and obtained the target compound (10).

In FIG. 2, 1H-NMR data of the compound of formula (10) is shown.

"Example 1"

As a commercial soft contact lens, 1 sheet of Etafilcon A (manufactured by vistakon, constituent monomer: HEMA, MAA) was added to 2.4 ml of methanol and 0.6 ml of water, and 50 mg of phosphorylcholine group-containing compound of formula (9) was added thereto. It stirred at 6 degreeC. After washing with water, a contact lens having a phosphorylcholine group introduced therein was obtained.

The molybdenum blue method quantified the amount of phosphorylcholine group introduced by the formula (9), which was 0.020 µmg / mg.

<Quantification method>

The obtained contact lens was wetted with perchloric acid, and heated to 180 deg. The obtained solution was diluted with water, and the ammonium molybdate hexahydrate tetrahydrate and L-ascorbic acid were added to it, and it developed for 5 minutes at 95 degreeC, the absorbance measurement of 710 nm was performed, and the introduction amount was calculated | required. An aqueous sodium dihydrogen phosphate solution was used for the calibration curve.

"Example 2"

As a commercial soft contact lens, one Nelfilcon A (CIBA, constituent monomer: modified PVA) was put in 2.4 ml of methanol-0.6 ml of water, and 50 mg of phosphorylcholine group-containing compound of formula (10) was added thereto. It stirred at 60 degreeC for 6 hours. After washing with water, a contact lens having a phosphorylcholine group introduced therein was obtained.

In the molybdenum blue method, the amount of phosphorylcholine group introduced by the formula (10) was quantitatively determined to be 0.015 µmg / mg.

"Example 3"

As a commercially available soft contact lens, one piece of Polymacon (manufactured by Baush & Lomb, constituent monomer: HEMA) was added to 2.4 ml of methanol and 0.6 ml of water, and 50 mg of phosphorylcholine group-containing compound of formula (10) was added thereto. It stirred at 6 degreeC. After washing with water, a contact lens having a phosphorylcholine group introduced therein was obtained.

The molybdenum blue method quantified the amount of phosphorylcholine group introduced in formula (1), which was 0.018 µmg / mg.

`` Comparative Examples 1 to 5 ''

As a comparison, the following commercial contact lenses were used.

Comparative Example 1.Etafilcon A (brand name: one day acube, J & J company)

Comparative Example 2. Etafilcon A (brand name: one-day akuair, Ocula Science company)

Comparative Example 3. Nelfilcon A (trade name: Focus Daily, Chiba Vision, Inc.)

Comparative Example 4.Polymacon (Brand Name: Medalist, Bausch & Lomb)

Comparative Example 5. Vifilcon A (brand name: Focus, Chiba Vision, Inc.)

`` Comparative Example 6 ''

Based on the technique of Patent Document 5, 10 mg of 1-α-glycerophosphorylcholine, 20 mg of 1,1-carbonyldiimidazole, and 20 mg of triethylamine were added to 3 ml of dimethyl sulfoxide, and at 50 ° C. Stir for 2 hours. In this solution, Polymacon used in Example 1 was immersed and reacted at room temperature for 12 hours. The contact lens was sufficiently washed with dimethyl sulfoxide, followed by water, and phosphorus was quantified. The introduced phosphorylcholine group was below 0.0001 μmol / mg, the detection limit, and the reaction did not proceed.

`` Comparative Example 7 ''

Based on the technique of Patent Document 5, 10 mg of 1-α-glycerophosphorylcholine, 20 mg of 1,1-carbonyldiimidazole, and 20 mg of triethylamine were added to 3 ml of dimethyl sulfoxide, and at 50 ° C. Stir for 2 hours. Nelfilcon A used in Example 2 was immersed in this solution, and it was made to react at room temperature for 12 hours. The contact lens was sufficiently washed with dimethyl sulfoxide, followed by water, and phosphorus was quantified. The introduced phosphorylcholine group was below 0.0001 μmol / mg, the detection limit, and the reaction did not proceed.

The result of the protein adsorption of Examples 1-2 and Comparative Examples 1-7 is shown in FIG. From this result, the contact lens obtained by the manufacturing method of the present invention significantly suppresses the adsorption of protein.

According to the present invention, protein adsorption of the contact lens is highly suppressed, and contamination by protein can be prevented remarkably.

The method of the present invention can be preferably used for soft contact lenses in which contamination of proteins is a fatal problem. It can be used especially suitably for the ionic soft contact lens which promotes protein adsorption.

Moreover, it can use suitably also for the oxygen permeability which a protein adsorbs easily, and the hard contact lens of continuous wearing.

Claims (10)

An ophthalmic lens material characterized by covalently bonding a phosphorylcholine group to an ophthalmic lens material surface by a post-treatment wherein the phosphorylcholine group-containing compound represented by the following formula (1) is reacted with an ocular lens material:

In formula, m is 2-6 and n is 1-4. In addition, -O- may be sufficient as -NH- of Formula (6). X ₁ , X ₂ and X ₃ are each independently a methoxy group, an ethoxy group or a halogen. However, up to two of X <_1> , X <_2> and X <_{3> may be} any of a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, and an isobutyl group. R is either of the structures in the following formulas (2) to (4), except that the compound of formula (1) is represented by A-R-B in the following formulas (2) to (4).

In Formulas (2) to (4), L represents 1 to 6 and P represents 0 to 3. An eyeball characterized in that the phosphorylcholine group is covalently bonded to the ophthalmic lens material surface by a post-treatment in which the phosphorylcholine group-containing compound represented by the following formulas (5) and / or (6) is reacted with the ocular lens material: Dragon lens material:

In formula, m is 2-6 and n is 1-4. X ₁ , X ₂ and X ₃ are each independently a methoxy group, an ethoxy group or a halogen. However, up to two of X <_1> , X <_2> and X <_{3> may be} any of a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, and an isobutyl group. Moreover, -O- may be sufficient as -NH- of Formula (6). The ophthalmic lens material according to claim 1 or 2, wherein the monomer constituting the ocular lens material contains a monomer having a hydroxyl group. The ophthalmic lens material according to claim 1 or 2, wherein the monomer constituting the ocular lens material contains a monomer having a carboxyl group. The ophthalmic lens material according to claim 1 or 2, wherein the monomer constituting the ocular lens material contains 2-hydroxyethyl methacrylate. The ophthalmic lens material according to claim 1 or 2, wherein the monomer constituting the ocular lens material contains vinyl alcohol. The ophthalmic lens material according to claim 1 or 2, wherein the monomer constituting the ocular lens material contains (meth) acrylic acid or (meth) acrylic acid ester. The ophthalmic lens material according to claim 1 or 2, wherein the monomer constituting the ocular lens material contains N-vinylpyrrolidone. A phosphorylcholine group is covalently bonded to the surface of an ophthalmic lens material by a post-treatment in which the phosphorylcholine group-containing compound according to claim 1 is reacted with an ocular lens material. Way. The post-treatment of reacting the phosphorylcholine group-containing compound according to claim 1 or 2 with the ophthalmic lens material, thereby covalently bonding the phosphorylcholine group to the surface of the ocular lens material to adsorb the protein to the ocular lens material. Method for preventing protein adsorption of the lens material for the eye, characterized in that to prevent.

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