CN1957288B - Method for producing protein adsorption-preventing ocular lens material - Google Patents

Abstract

Disclosed is a method for producing an ocular lens material which comprises a step for reacting and covalently bonding a compound having a phosphorylcholine group represented by the formula (1) below with the surface of an ocular lens material. This method for producing an ocular lens material is characterized in that a compound having a terminal amino group is introduced into the surface of the ocular lens material and then a compound represented by the formula (2) or (3) below is introduced thereinto through the compound having the terminal amino group. The object of the present invention is to provide a method of manufacturing a contact lens that prevents protein adsorption. In the formula (2), n is a natural number of 1-18.

Description

Method for producing eyeglass material that prevents protein adsorption

technical field

The present invention relates to a method for producing lens materials such as contact lenses and a method for preventing protein adsorption. More specifically, it relates to a method for preventing protein fouling by treating the surface of lens materials (especially contact lenses) by post-treatment with phosphorylcholine group-containing compounds.

Background technique

It is a known method to polymerize phosphorylcholine group-containing monomers and use them as contact lens materials (Patent Documents 1-3). For example, Patent Document 1 discloses a water-containing soft contact lens containing a phosphorylcholine group-containing (meth)acrylate as a constituent unit, and describes that it is excellent in water content, oxygen permeability, and tensile strength, and has excellent protein adsorption properties. A small amount can suppress the adhesion of dirt.

Regarding post-treatment methods for contact lenses, Patent Document 4 describes: polymerizing phosphorylcholine group-containing monomers on the surface of contact lenses to produce contact lenses with a hydrophilic surface and less protein adsorption.

Patent Document 5 discloses a method of chemically bonding a low-molecular phosphorylcholine compound to the surface of a contact lens to reduce protein adsorption.

That is, Example 5 of Patent Document 5 describes a method in which glycerophosphorylcholine is treated with 1,1'-carbonyldiimidazole to introduce phosphorylcholine groups into the surface of a contact lens containing a hydroxyethyl methacrylate copolymer. However, when a verification test was carried out on the above reaction, the desired phosphorylcholine-treated contact lens could not be obtained.

Reaction Formula 6 of Patent Document 5 describes the chemical structural formula in which the phosphorylcholine carboxyl compound is converted into an active ester. All there is no record about its synthetic method, embodiment, therefore can't carry out verification test, but according to common organic chemistry general knowledge, when synthesizing the phosphorylcholine carboxyl compound with the recorded structure, its method is extremely complicated, and yield is low, Its lack of utility can thus be easily deduced by analogy.

As described above, the treatment method described in Patent Document 5 does not describe a method for synthesizing a carboxyl group-containing phosphorylcholine group-containing compound for treating contact lenses, and the described method cannot be immediately implemented. In addition, the reaction of introducing phosphorylcholine groups to the surface of contact lenses cannot sufficiently proceed under the conditions described in these patent documents, and the introduction amount is low, so the excellent effect of preventing protein adsorption cannot be exhibited.

On the other hand, stains on contact lenses are caused by the adsorption of proteins or lipids contained in tears to become stains, which may cause eye diseases such as allergies and infections (Non-Patent Document 1). In particular, the water-containing soft contact lens mainly composed of 2-hydroxyethyl methacrylate polymer or the highly water-containing soft contact lens obtained by copolymerizing a small amount of methacrylic acid as an ionic monomer, or as a hydrophilic single contact lens In soft contact lenses mainly composed of polymers of N-vinylpyrrolidone or N,N-dimethylacrylamide, protein fouling is a fatal problem.

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

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

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

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

Patent Document 5: Japanese Patent Application Publication No. 5-505121

Non-Patent Document 1: "Staining of Soft Contact Lenses and Its Analysis", Material Stealth, Vol.4, No.1, 2004

Contents of the invention

The invention provides a contact lens. After post-processing the contact lens, the phosphorylcholine group is covalently bonded to the surface of the contact lens through a compound having an amino terminal group, thereby inhibiting protein adsorption to the contact lens and preventing protein dirt.

That is, the purpose of the present invention is not to polymerize phosphorylcholine group-containing monomers to produce contact lenses that prevent protein adsorption as in the methods described in the above-mentioned Patent Documents 1-3, but to post-process the contact lenses to It has an excellent function of preventing protein adsorption.

The object of the present invention is not to polymerize a phosphorylcholine group-containing monomer on the surface of a contact lens as in the method described in Patent Document 4, and cover it with another polymer different from the contact lens, thereby introducing a phosphorylcholine group. , instead of covering with a polymer, it is directly covalently bonded to the phosphorylcholine group, thereby obtaining excellent durability, without changing the original properties of the contact lens due to the covering of the polymer, and can exert an excellent effect of preventing protein adsorption.

The object of the present invention is not that, like the method described in Citation Document 5, it is not possible to introduce enough phosphorylcholine groups into the contact lens surface during the verification test, but it can introduce a sufficient amount of phosphorylcholine groups to exert an excellent preventive effect. The effect of protein adsorption.

In particular, the essential difference between the present invention and the method shown in Patent Document 5 is that in the present invention, it is characterized in that a compound having terminal amino groups is introduced into the surface of the lens material, and through the compound, the low molecular weight, formula (2) or The phosphorylcholine group-containing compound of (3) is chemically bonded to the contact lens surface, thereby suppressing deformation of the lens and effectively suppressing protein adsorption. That is, when a phosphorylcholine group is directly introduced into a functional group present on the surface of a contact lens, the lens tends to swell slightly due to its high hydrophilicity, but by introducing it between the lens surface and the phosphorylcholine group An alkyl group or an alkoxy group having amino groups at both ends can easily control the expansion. The lower the hydrophilicity of the compound having an amino group, the more effective it is to suppress lens swelling. Alkyl chain lengths of 0-6 are most preferred to control swelling. In the case of an oxyalkylene group, the influence of the chain length is small.

That is, the present invention provides a method for producing an eyeglass material, the method having a step of reacting a compound having a phosphorylcholine group represented by the following formula (1) with the surface of the eyeglass material to bond covalently, characterized in that: An amino compound is introduced into the surface of the lens material, and then a compound of the following formula (2) is introduced via the above-mentioned compound having a terminal amino group.

[chemical 5]

[chemical 6]

n is a natural number from 1 to 18

(2)

The present invention also provides a method for producing a spectacle material, which has a step of reacting a compound having a phosphorylcholine group represented by the following formula (1) with the surface of the spectacle material to form a covalent bond, which is characterized in that: A compound having a terminal amino group is introduced into the surface of a lens material, and then a phosphorylcholine group-containing compound of the following formula (3) is introduced via the compound having a terminal amino group.

[chemical 7]

[chemical 8]

The present invention provides the manufacturing method of the above-mentioned spectacle material, characterized in that: the above-mentioned compound with terminal amino group is an alkyl group having C0 (hydrazine) to C12, an oxirane group with a degree of polymerization of 1 to 10, and a degree of polymerization of 1 A compound having a propylene oxide group of ~10, an aziridine with a degree of polymerization of 1 to 20, a compound of 2-methyl aziridine with a degree of polymerization of 1 to 20, a compound having piperazine or aniline.

The present invention also provides a method for preventing protein adsorption by lens materials, which is characterized in that: a compound having terminal amino groups is introduced into the surface of the lens materials, and then the phosphorylcholine group is converted into phosphorylcholine The base is covalently bonded to the surface of the lens material, preventing the adsorption of proteins to the lens material.

The present invention also provides a method for preventing protein adsorption of lens materials, which is characterized in that: amino groups are introduced into the phosphorylcholine group-containing compound of the upward formula (2) or (3), and then reacted with the surface of the lens material, The phosphorylcholine group is covalently bonded to the surface of the lens material to prevent the adsorption of protein to the lens material.

The present invention also provides an eyeglass material, which introduces a spacer group between the surface of the eyeglass material and the imported compound having a phosphorylcholine group of formula (2) or (3) through an amide bond or an alkylamine bond .

According to the production method of the present invention, any amount of phosphorylcholine groups can be covalently bonded to the surface of the lens material through a compound having a terminal amino group by a simple post-treatment method.

The lens material of the present invention, the contact lens, covalently bonds the phosphorylcholine group to the surface of the contact lens through a compound having an amino terminal group, thereby effectively inhibiting protein adsorption to the contact lens and exerting an excellent antifouling effect. It also improves water retention and improves wearing comfort.

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

The introduction of phosphorylcholine groups is not covered by polymers, so the durability is excellent, and the original properties of contact lenses are basically not deteriorated.

The contact lens obtained by this invention is a contact lens excellent in wearing feeling. Therefore, it is preferably used in contact lenses that tend to feel a foreign body sensation due to reasons such as poor flexibility of the material.

In particular, the reaction yields of compounds having terminal amino groups with compounds of formula (2) and formula (3) are excellent, and it is easy to control the introduction amount. Therefore, there is an excellent effect that the phosphorylcholine group of the formula (1) can be introduced into the contact lens surface with extremely high efficiency.

According to this method, the deformation of the lens can also be suppressed, and at the same time, the adsorption of proteins can be effectively suppressed. That is, when a highly hydrophilic functional group is directly introduced into a functional group existing on the surface of a contact lens, the lens tends to swell slightly, but by selecting a functional group having amino groups at both ends between the lens surface and the phosphorylcholine group, By controlling its polarity, its expansion can be easily controlled.

Brief description of the drawings

FIG. 1 is a graph of protein adsorption amounts of contact lenses of Examples and Comparative Examples.

Detailed ways

The present invention will be described in detail below.

"Compounds with a terminal amino group"

The compounds with amino groups used in the present invention are: hydrazine, ethylenediamine, propylenediamine, 1,4-diaminobutane, 1,6-diaminohexane, piperazine, ethylene glycol bis(2-amino Ethyl) ether, ethylene glycol bis(3-aminopropyl) ether, etc., all of the above can be purchased as reagents. Its polarity is also within a range that prevents swelling. In addition, compounds having three or more terminal amino groups such as tris(2-aminoethyl)amine or amino-terminal dendrimers can also be effectively used as the compound having amino groups used in the present invention.

"Method for preparing phosphorylcholine group-containing compound of formula (2)"

Phosphorylcholine can be completely synthesized. However, the synthesis conditions are complicated, must be strict anhydrous conditions, and the production cost is high.

On the other hand, phosphorylcholine can be extracted in the form of lecithin, which is a constituent of the cell membrane. In this case, 1-α-glycerophosphocholine can be obtained easily and at a lower cost by removing the fatty acid moiety by hydrolysis. The inventors of the present invention have found that a carboxyl-containing phosphorylcholine group-containing compound can be easily obtained by oxidatively cleaving the diol portion of this 1-α-glycerophosphorylcholine.

The most representative synthesis method is: oxidizing 1-α-glycerophosphorylcholine in water, acetonitrile and other solvents with sodium periodate and ruthenium trichloride to obtain the target carboxyl compound.

The compound of formula (2) is preferably carboxymethylphosphorylcholine obtained by oxidative cleavage of 1-α-glycerophosphorylcholine (when n=1).

"Preparation of carboxymethylphosphorylcholine by oxidative cleavage of 1-alpha-glycerophosphorylcholine"

1-α-Glycerophosphorylcholine can be oxidized and cracked by periodate and ruthenium trichloride in a mixed solvent of water and acetonitrile to produce carboxymethylphosphorylcholine.

That is, as shown in Examples, 5 g of 1-α-glycerophosphorylcholine was dissolved in 70 ml of water-30 ml of acetonitrile. 17g of sodium periodate and 80mg of ruthenium trichloride were added under ice-cooling, stirred overnight, the precipitate was filtered, concentrated under reduced pressure, and extracted with methanol to obtain 3.86g (yield 82%) of the target carboxymethylphosphorylcholine.

"Method for preparing phosphorylcholine group-containing compound of formula (3)"

Oxidative cleavage of the known glycerophosphorylcholine is performed by known methods. For example, 1,2-diol is oxidized using an oxidizing agent such as periodic acid, periodate, or bismuth trioxide to cleave the bond to obtain an aldehyde. The reaction is usually carried out in water or an organic solvent containing water, and the reaction temperature is from 0°C to room temperature. After an equilibrium reaction in water, the aldehyde body also forms a hydrate, which has no effect on the subsequent reaction with the amine. An example of a scheme for the preparation of monofunctional aldehydes containing phosphorylcholine groups is given below.

[chemical 13]

"glass material"

In the present invention, the spectacle material is a molded product of a material worn in eyes. Mainly contact lenses. Contact lenses can be of any material. For example, the contact lenses of the present invention can be manufactured from the following contact lenses: namely, from 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 alkane, hexafluoroisopropyl methacrylate, perfluoroalkyl methacrylate, siloxane methacrylate (Siloxanil) ester (SiMA), siloxane styrene (SiSt), ethyl dimethacrylate Polymers of glycol esters (EGDMA), allyl methacrylate (AMA), silicone macromers, etc., or copolymers of two or more monomers.

As monomers constituting contact lenses, soft contact lenses mainly composed of 2-hydroxyethyl methacrylate and ionic soft contact lenses obtained by copolymerizing methacrylic acid are typical soft contact lenses. Proteins are easily adsorbed. Treatment by the method of the invention is therefore preferred.

The preferred monomers of this invention are acrylic acid or methacrylic acid. If acrylic acid or methacrylic acid is contained in the monomer constituting the contact lens, since the surface of the contact lens has a carboxyl group, the above-mentioned compound having amino groups at both terminals can be easily introduced through an amide bond.

Even in contact lenses without carboxyl groups, carboxyl groups can be introduced by surface modifiers or plasma treatment. The specific introduction method by plasma treatment is as follows.

<Introduction of Carboxyl Groups by Surface Reaction by Plasma Treatment>

Carboxyl groups are introduced to the surface of contact lenses by low-temperature plasma in a carbon dioxide atmosphere. Specifically, a contact lens is put into a plasma reaction container, the inside of the reaction container is evacuated by a vacuum pump, and then carbon dioxide is introduced. Then, glow discharge is performed, and carboxyl groups can be introduced into the surface of the contact lens.

"Preparation"

First, a compound having a terminal amino group is covalently bonded (amide bond) to a carboxyl group of a contact lens constituting monomer or a carboxyl group newly introduced to the surface of a contact lens by plasma treatment or the like by a conventional method.

Specifically, contact lenses made of poly-HEMA were placed in a plasma reaction vessel (BP-1 manufactured by SamCointa Nashiyonal Research Institute), the air in the vessel was completely replaced with carbon dioxide, and anodic treatment was carried out at room temperature for 10 minutes ( RFPower100), import carboxyl group. Next, carbonyldiimidazole or 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and other carbodiimide coupling agents, or thionyl chloride, pentachloride Contact lenses treated in the presence of phosphorus, phosphorus oxychloride, phosphorus tribromide, oxalyl chloride, etc. are immersed in water or an organic solvent containing an excess of a compound having amino groups at both terminals, undergo amidation reaction, introduce amino groups to the terminals, and then wash.

Next, the compound of formula (2) or (3) is amide bonded to the unreacted amino group.

Specifically, when it is a compound of formula (2), dissolve or disperse the compound (2) in water or organic solvents such as N, N-dimethylformamide, acetonitrile, dimethyl sulfoxide, and add carbonyldiimidazole Or 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide coupling agent such as carbodiimide hydrochloride, or thionyl chloride, etc., to make active ester or acid chloride, and Amino surface of contact lenses undergoes amidation reaction.

When it is a compound of formula (3), the compound of (3) is dissolved in protic solvents such as water or methanol or solvents containing these substances, the contact lens is immersed, reacted for 4 hours, then sodium cyanoborate is added, stirred overnight, and then washing.

As a result, the phosphorylcholine group of the formula (1) can be introduced into the surface of the contact lens via the compound having the terminal amino group.

The introduction of a compound having amino groups at both terminals can be reacted under the same conditions as long as it is within the described range.

Amino groups can also be directly introduced into contact lenses by plasma treatment. Known methods are as follows.

<Introduction of amino group by surface reaction of plasma treatment>

Amino groups are introduced to the contact lens surface by low-temperature plasma under nitrogen atmosphere. Specifically, contact lenses were placed in a plasma reaction container, the inside of the reaction container was evacuated by a vacuum pump, and then nitrogen gas was introduced. Next, amino groups can be introduced to the lens surface by glow discharge. The relevant literature on plasma treatment is listed below.

1. M. Muller, C. oehr

Plasma aminofunctionalisation of PVDF microfiltration membranes: comparison ofthe in plasma modifications with a grafting method using ESCA and anamino-selective fluorescent probeSurface and Coatings Technology 116-119(1999)802-807

2. Lidija Tusek, Mirko Nitschke, Carsten Werner, Karin Stana-Kleinschek, Volker Ribitsch

Surface characterization of NH3 plasma treated polyamide 6 foilsColloids and Surfaces A: Physicochem.Eng.Aspects 195(2001)81-95

3. Fabienne Poncin-Epaillard, Jean-Claude Brosse, Thierry FalherReactivity of surface groups formed onto a plasma treated poly(propylene) filmMacromol.Chem.Phys.200.989-996(1999)

Example

Hereinafter, the present invention will be described in further detail based on examples. The present invention is not limited by these Examples.

"Synthesis of compounds of formula (2)"

Dissolve 5g of 1-α-glycerophosphorylcholine in 70ml of water-30ml of acetonitrile. Add 17 g of sodium periodate and 80 mg of ruthenium trichloride under ice cooling, and stir overnight. The precipitate was filtered, concentrated under reduced pressure, and extracted with methanol to obtain 3.86 g (yield 82%) of the target carboxymethylphosphorylcholine.

Carboxymethylphosphorylcholine is a compound of formula (2) when n=1.

"Synthesis of compounds of formula (3)"

Dissolve 450mg of 1-α-glycerophosphorylcholine in 15ml of distilled water and cool in an ice-water bath. Add 750 mg of sodium periodate, and stir for 5 hours. The reaction solution was concentrated under reduced pressure, dried under reduced pressure, and the target substance was extracted with methanol.

"Example 1" <Contact lens having compound of formula (2) (spacer: ethylenediamine)>

One piece of commercially available soft contact lens Etafilcon A (trade name Wande Akuubiya, manufactured by J&J, constituent monomer: HEMA-MAA) was immersed in 3 ml of water, and 30 mg of ethylenediamine, 10 mg of 1-ethyl-3-( 3-dimethylaminopropyl) carbodiimide hydrochloride, 6mg N-hydroxysuccinimide, stirred at room temperature for 3 hours. The contact lens was thoroughly washed with pure water, immersed in 3 ml of water, and then 10 mg of the compound of chemical formula (2), 10 mg of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 6 mg of N-hydroxysuccinimide, stirred at room temperature for 3 hours, and then washed thoroughly with water to obtain a contact lens in which the target phosphorylcholine group is chemically bonded to the surface.

"Example 2" <Contact lens having compound of formula (3) (spacer: ethylenediamine)>

One piece of commercially available soft contact lens Etafilcon A (trade name Wanda Akuyubi, manufactured by J&J, constituent monomer: HEMA-MAA) was immersed in 3 ml of water, and 30 mg of ethylenediamine, 10 mg of 1-ethyl-3-(3 -Dimethylaminopropyl) carbodiimide hydrochloride, 6 mg of N-hydroxysuccinimide, stirred at room temperature for 3 hours. Fully wash the contact lens with pure water, immerse it in 3ml of water, then add 10mg of the compound of chemical formula (3), stir at room temperature for 4 hours, then add 3mg of sodium cyanoborate, stir overnight, and fully wash with water to obtain the target phosphoric acid chol Contact lenses with bases chemically bonded to the surface.

"Example 3" <Contact lens having compound of formula (2) (spacer: 1,6-diaminohexane)>

One piece of commercially available soft contact lens Etafilcon A (trade name WANDA アキユビュ, manufactured by J&J, constituent monomer: HEMA-MAA) was immersed in 3 ml of N,N-dimethylformamide, and 50 mg of 1,6- Diaminohexane, 10 mg 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride, 6 mg N-hydroxysuccinimide, stirred at room temperature for 3 hours. The contact lens is fully washed with N,N-dimethylformamide, immersed in 3ml N,N-dimethylformamide, then the compound of 10mg chemical formula (2) and 1ml will 6mg thionyl chloride in N,N - Stirring in dimethylformamide for 30 minutes and mixing the resulting solutions, reacting for 4 hours, and washing thoroughly with water to obtain a contact lens in which the target phosphorylcholine group is chemically bonded to the surface.

"Example 4" <Contact lens having compound of formula (2) (separating group: ethylene glycol bis(2-aminoethyl) ether)>

One piece of commercially available soft contact lens Etafilcon A (trade name Wande Akuyubiyu, manufactured by J&J, constituent monomer: HEMA-MAA) was immersed in 3 ml of N,N-dimethylformamide, and 62 mg of ethylene glycol diol was added. (2-aminoethyl) ether, 10mg 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride, 6mg N-hydroxysuccinimide, stirred at room temperature for 3 hours . The contact lens is fully washed with N,N-dimethylformamide, immersed in 3ml N,N-dimethylformamide, then the compound of 10mg chemical formula (2) and 1ml will 6mg thionyl chloride in N,N - Stirring in dimethylformamide for 30 minutes and mixing the resulting solutions, reacting for 4 hours, and washing thoroughly with water to obtain a contact lens in which the target phosphorylcholine group is chemically bonded to the surface.

"Comparative examples 1 to 5"

The following commercially available contact lenses were used as comparative products.

Comparative Example 1. Etafilcon A (trade name: Wonder Akubiyu, manufactured by J&J)

Comparative Example 2. Etafilcon A (trade name: manufactured by Wonder Aqua A, Okiura Cyence)

Comparative Example 3. Nelfilcon A (trade name: Fokas Dairy Izu, manufactured by Chiba Bijinyon)

Comparative Example 4. Polymacon (trade name: Medallist, manufactured by Boshilum)

Comparative Example 5. Vifilcon A (trade name: Fo-Kas, manufactured by Chibabijiyon)

Comparative Example 6. Comparative Example 1

Comparative Example 7. Comparative Example 2

"Comparative Example 6"

According to the method 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 stirred at 50°C for 2 hours. The Polymacon used in Example 1 was immersed in this solution and reacted at room temperature for 12 hours. The contact lens was thoroughly washed with dimethyl sulfoxide and then water, and phosphorus was quantified. The introduced phosphorylcholine group was below the detection limit of 0.0001 μmol/mg, and the reaction did not proceed.

"Comparative Example 7"

According to the method 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 stirred at 50°C for 2 hours. Nelfilcon A used in Example 2 was immersed in this solution and reacted at room temperature for 12 hours. The contact lens was thoroughly washed with dimethyl sulfoxide, followed by water, and phosphorus was quantified. The introduced phosphorylcholine group was below the detection limit of 0.0001 μmol/mg, and the reaction did not proceed.

The protein adsorption results of Examples 1-4 and Comparative Examples 1-7 are shown in FIG. 1 . From this result, it can be seen that the contact lens of the present invention significantly suppresses protein adsorption.

Industrial applicability

According to the present invention, protein adsorption to contact lenses can be highly suppressed, and protein soiling can be remarkably prevented.

The method of the present invention is preferably utilized in soft contact lenses where protein fouling is a fatal problem. It is particularly preferably utilized in ionic soft contact lenses that promote protein adsorption.

Claims (6)

1. The treatment method of contact lens, the treatment method of this contact lens has the operation that makes the compound with phosphorylcholine group shown in following formula (1) react with the surface of contact lens and covalently bond, it is characterized in that: will have The compound of the terminal amino group is introduced into the surface of the contact lens, and then, the phosphorylcholine group-containing compound of the following formula (2) is introduced via the above-mentioned compound having the terminal amino group, 2. The treatment method of contact lens, the treatment method of this contact lens has the operation that makes the compound that has the phosphorylcholine group shown in following formula (1) react with the surface of contact lens and covalently bond, it is characterized in that: will have The compound of the terminal amino group is introduced into the surface of the contact lens, and then the phosphorylcholine group-containing compound of the following formula (3) is introduced via the above-mentioned compound having the terminal amino group,

3. The treatment method of contact lenses according to claim 1 or 2, characterized in that: the above-mentioned compound having terminal amino groups is an alkyl group having C0 to C12, an oxirane group having a degree of polymerization of 1 to 10, and a degree of polymerization of 1 A compound having a propylene oxide group of ~10, an aziridine with a degree of polymerization of 1 to 20, or a compound of 2-methyl aziridine with a degree of polymerization of 1 to 20. 4. The method for preventing contact lens from adsorbing proteins is characterized in that: the surface of the contact lens is introduced into a compound with terminal amino groups, and then by making the phosphorylcholine-containing compound of the following formula (2) or (3) react with the contact lens post-treatment to make the phosphorylcholine group covalently bonded to the surface of the contact lens to prevent the adsorption of protein to the contact lens, 5. The method that prevents contact lens from adsorbing protein is characterized in that: introduce amino group in the phosphorylcholine group-containing compound of downward formula (2) or (3), then by the processing that reacts with the surface of contact lens, make phosphorylcholine The base is covalently bonded to the surface of the contact lens, preventing the adsorption of the protein to the contact lens, 6. Contact lenses, which are soft contact lenses mainly composed of 2-hydroxyethyl methacrylate as a monomer constituting contact lenses, or obtained by copolymerizing methacrylic acid and 2-hydroxyethyl methacrylate An ionic soft contact lens, wherein a compound having a phosphorylcholine group represented by the following formula (2) or (3) is introduced on the surface thereof via a compound having a terminal amino group,

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