JP2000010054A - Hydrophilic lens for eye and hydrophilic treatment - Google Patents

Abstract

PROBLEM TO BE SOLVED: To improve the wettability with a tear and the fitting feeling with an easy operation and to give hydrophilicity durable against daily care such as cleaning with fingers by immersing a lens for eyes in an aq. soln. containing a hydrophilic monofunctional photopolymerizable monomer and a hydrophilic polyfunctional photopolymerizable monomer and irradiating the lens with UV rays. SOLUTION: A lens for eyes is immersed in an aq. soln. containing a hydrophilic monofunctional monomer and a polyfunctional monomer which are photopolymerizable monomers singly and then, irradiated with UV rays. As for the hydrophilic monofunctional photopolymerizable monomer, for example (meth)acrylic acid and itaconic acid can be used. As for the hydrophilic polyfunctional photopolymerizable monomer, for example polyethylene glycol di(meth)acrylate (having n=1 to 50 of ethylene glycol units) is used. The content of the monomer component in the aq. soln. is 0.001 to 20 wt.% in total of the monofunctional monomers and polyfunctional monomers, preferably 0.1 to 10 wt.%.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

[0001] The present invention relates to a hydrophilic ophthalmic lens and a hydrophilic treatment method. More specifically, the present invention relates to a surface treatment method capable of imparting good hydrophilicity to an ophthalmic lens such as a contact lens or an intraocular lens having a hydrophobic surface, and a hydrophilic ophthalmic lens obtained by the treatment method. Things.

[0002]

2. Description of the Related Art In recent years, various methods have been studied as a method for hydrophilizing a surface of an ophthalmic lens. For example, a method is known in which a contact lens is immersed in a solution containing a hydrophilic polymer and then contacted with a solution containing a cross-linking agent to cross-link the hydrophilic polymer on the lens surface (JP-A-4-104220). ).

However, in the above method, even though the hydrophilic monomer is crosslinked, the durability is poor because only the hydrophilic polymer itself to be crosslinked is adsorbed (physical bond) on the lens surface.

Japanese Patent Application Laid-Open No. 8-13667 discloses a polymer obtained by synthesizing a monomer having a photoreactive group obtained by synthesizing a photosensitizer having no functional group and a monomer, and a hydrophilic monomer. The hydrophilic polymer is immobilized on the lens surface by immersing the lens in an aqueous solution and irradiating the lens with light.

[0005] However, the above method involves synthesizing a monomer having a photoreactive group, further synthesizing the monomer with a hydrophilic monomer to synthesize a hydrophilic polymer having a photoreactive group, and then preparing an aqueous solution containing the hydrophilic polymer. Complicated work is necessary until the contact lens is immersed and irradiated with light. Further, since the hydrophilic groups on the lens surface are not cross-linked to each other, the durability is poor.

[0006]

SUMMARY OF THE INVENTION An object of the present invention is to provide an ophthalmic lens, for example, a contact lens, with a hydrophilic surface by a simple operation to improve the wettability with tears and improve the feeling of wearing. An object of the present invention is to provide a hydrophilic treatment method that can withstand daily care such as washing, and a hydrophilic lens obtained by the treatment method. In addition, in the case of an intraocular lens, by providing a hydrophilic treatment method and a hydrophilic lens obtained by the treatment method, which improves wettability and smoothes the lens insertion work, and also imparts stain resistance. is there.

[0007]

According to the present invention, in order to solve the above-mentioned problems, an ophthalmic lens is immersed in an aqueous solution containing a hydrophilic monofunctional monomer and a polyfunctional monomer which are photopolymerizable monomers alone. It is characterized by irradiation with ultraviolet rays.

The above-mentioned photopolymerizable monomer generates radicals by itself when irradiated with ultraviolet rays, without a photosensitizer (initiator). The photopolymerizable monofunctional monomer activated by irradiating ultraviolet rays is bonded to the lens surface to impart hydrophilicity, and the photopolymerizable polyfunctional monomer is bonded to the lens surface, or is combined with the photopolymerizable monofunctional monomer. It is considered that the hydrophilic monomer is improved and the durability is further increased due to the complicated intertwining of the hydrophilic monomers on the lens surface upon crosslinking.

In addition, by binding a hydrophilic photopolymerizable monomer such as polyethylene glycol to the lens surface, the biocompatibility of the ophthalmic lens can be improved, and the amount of protein attached can be reduced. At the same time, a stain-resistant treatment can be performed.

[0010]

BEST MODE FOR CARRYING OUT THE INVENTION The hydrophilic monofunctional photopolymerizable monomer includes, for example, (meth) acrylic acid, itaconic acid,
(Meth) acrylamide, N-methyl (meth) acrylamide, N-ethyl (meth) acrylamide, N, N-
Dimethyl (meth) acrylamide, N, N-diethyl (meth) acrylamide, N-methylol (meth) acrylamide, N-ethylaminoethyl (meth) acrylamide, diacetone (meth) acrylamide, N-vinylpyrrolidone, N- (meth) Acryloylpyrrolidone,
2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, glycidyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, glycerol (meth) acrylate, (methoxy) polyethylene glycol (meth) acrylate (ethylene glycol Site n = 1 to 50). Representative examples of the hydrophilic polyfunctional photopolymerizable monomer include polyethylene glycol di (meth) acrylate (ethylene glycol moiety n = 1 to 50).

In the present invention, it is possible to use a hydrophobic monofunctional or polyfunctional monomer as long as the hydrophilicity-imparting effect is not impaired.

The content of the monomer component in the aqueous solution is as follows:
0.001 in total of monofunctional monomer and polyfunctional monomer
-20% by weight, preferably 0.1-10% by weight. If it is less than 0.001% by weight, it is difficult to impart hydrophilicity to the lens surface, and if it exceeds 20% by weight, the lens surface tends to become cloudy.

The ultraviolet irradiation time is usually 5 to 1
20 minutes, considering the hydrophilizing effect and lens deterioration, etc.
60 minutes is preferred.

The ultraviolet irradiation in the present invention may take any form as long as it can irradiate the contact portion between the aqueous hydrophilic polymer solution and the ophthalmic lens. Use of an electron beam or the like in addition to ultraviolet rays is also within the scope of the present invention.

The ophthalmic lens is not limited to hard or soft, and can be applied to a contact lens, an intraocular lens, and the like.

It is also within the scope of the present invention that the ophthalmic lens is previously irradiated with plasma in order to enhance the reactivity between the ophthalmic lens surface and the hydrophilic photopolymerizable monomer. The working gas may be an inert gas or an active gas, but is preferably an argon gas from the viewpoint of radical surface activity. The action time is usually 1 second to 20 minutes, but is preferably 20 seconds to 6 minutes in consideration of the deterioration of the lens, the efficiency and simplicity of the operation, and the effect of activating the surface.

It is also within the scope of the present invention to add a photosensitizer to the solution in order to further increase the reactivity between the ophthalmic lens surface and the hydrophilic monomer. For example, sodium dimethyldithiocarbamate, sodium diethyldithiocarbamate, diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, p-isopropyl-α-hydroxyisobutylketone, 2,2-dimethoxy-2 -Phenylacetophenone, α, α-dichloro-4-phenoxyacetophenone, benzyldimethylketal, 1-hydroxycyclohexyl-phenylketone, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzoin-n-butyl ether,
2,2'-azobisisobutyronitrile, 1,1'-azobis (cyclohexane-1-carbonitrile), 2,
2'-azobis (2-methylbutyronitrile), 2,
2'-azobis (2,4-dimethylvaleronitrile),
2,2'-azobis (4-methoxy-2,4-dimethylvaleronitrile), dimethyl 2,2'-azobisisobutyrate, 2,2'-azobis (2,4,4-trimethylpentane), benzoyl peroxide, Diisopropyl peroxydicarbonate, lauroyl peroxide,
Stearoyl peroxide, tert-butyl peroxybivalate, bis (4-tert-butylcyclohexyl) peroxydicarbonate, α, α'-bis (tert-butylperoxy) diisopropylbenzene, dicumyl peroxide, 2,5- Dimethyl,
2,5-bis (tert-butylperoxy) hexane and the like. These photosensitizers are usually 0.0001
To 5% by weight, and preferably 0.0005 to 1% by weight in view of solubility and the like.

Next, embodiments of the present invention will be described, but the present invention is not limited to only such embodiments.

Example 1 An oxygen-permeable contact lens was prepared by copolymerizing 50 parts by weight of siloxanyl methacrylate, 20 parts by weight of fluoroalkyl methacrylate, 20 parts by weight of methyl methacrylate, and 10 parts by weight of methacrylic acid. In addition, polymethyl methacrylate (PMM
An intraocular lens consisting of A) was prepared.

Acrylamide 1% by weight using distilled water,
The aqueous solution was adjusted so as to be 0.1% by weight of polyethylene glycol diacrylate (ethylene glycol moiety n = 9), placed in a sample tube, and replaced with nitrogen gas. The contact lens and the intraocular lens were immersed in the aqueous solution, and ultraviolet rays were uniformly irradiated on both surfaces of the lens for 30 minutes using a high-pressure mercury lamp (manufactured by Mitsubishi Rayon Co., Ltd.) as a light source.

After the ultraviolet irradiation, the contact lens and the intraocular lens were taken out of the aqueous solution, and each lens surface was scrubbed with a finger using a detergent. The lens surface was rubbed back and forth about 200 times, then washed with water and dried. The above series of operations was defined as one cycle, and after performing 10 cycles on the lens subjected to the hydrophilization treatment of the present invention, the contact angle was measured by a liquid appropriate method. Further, the difference in the lens surface state before and after the treatment with the naked eye and the change in the lens shape were evaluated. Table 1 shows the results.

Example 2 An aqueous solution consisting of 2% by weight of glycerol methacrylate and 0.1% by weight of polyethylene glycol dimethacrylate (ethylene glycol moiety n = 23) was prepared and subjected to a hydrophilizing treatment in the same manner as in Example 1. evaluated. Table 1 shows the evaluation results.

Example 3 An aqueous solution comprising 1% by weight of polyethylene glycol methacrylate (ethylene glycol moiety n = 23) and 0.1% by weight of polyethylene glycol diacrylate (ethylene glycol moiety n = 9) was prepared. Hydrophilic treatment was performed in the same manner as described above, and the evaluation was performed. Table 1 shows the evaluation results.

(Example 4) An aqueous solution was prepared so as to be 2% by weight of 2-hydroxyethyl methacrylate and 0.1% by weight of polyethylene glycol diacrylate (ethylene glycol moiety n = 9). A hydrophilic treatment was performed and evaluated. Table 1 shows the evaluation results.

(Comparative Examples 1 to 4) In Examples 1 to 4, the contact lens and the intraocular lens were immersed in an aqueous solution at room temperature for 30 minutes without irradiation with ultraviolet rays. Example 1
The evaluation was performed in the same manner as described above, and the evaluation results are shown in Table 1.

[0026]

* Lens surface change: No change in the lens surface condition before and after the treatment with the naked eye = ○ 〃

* Change in lens shape: The change in lens shape was observed with a laser interferometer (FIX05, manufactured by Fuji Photo Optical Co., Ltd.).

[0029] Shape change before and after treatment was 0 to less than 1% = ○ 〃 1% or more = ×

* Evaluation of stain resistance: The stain resistance of the lens subjected to the hydrophilic treatment was evaluated by the micro BCA method and the vanillin method.

The amount of protein / lipid stain adhered to the lens before treatment was less than half of the amount after treatment and the stain resistance was improved, and the stain resistance was improved. ○ The amount of adhesion hardly changed and the stain resistance was not improved = ×

From the results shown in Table 1, it can be seen that the hydrophilizing treatment according to the present invention surely hydrophilizes the lens surface without deteriorating the lens surface or changing its shape. Furthermore, it is considered that the surface of the lens and the hydrophilic monomer are strongly bonded because of the durability.

[0033]

The hydrophilization treatment of the present invention improves the wettability of the ophthalmic lens, for example, a contact lens, with tears, improves the feeling of wearing, and withstands daily care such as hand washing with a simple operation. It imparts the obtained hydrophilicity. In addition, in the case of an intraocular lens, an excellent effect of improving the wettability and smoothing the lens insertion operation and suppressing the contamination resistance, for example, the adhesion of a protein or the like is provided.

 ──────────────────────────────────────────────────続 き Continued on the front page (72) Inventor Kenji Uno 2-40-2 Hongo, Bunkyo-ku, Tokyo F-term in the seed company (reference) 2H006 BB04 BB10 BC05 2K009 BB14 CC24 DD02 DD05 EE00 4C081 AB22 AB23 BB01 BB04 BB09 BC02 CA042 CA062 CA072 CA081 CA082 CA102 CA131 CA271 CC06 CE08 DA01 DC03 DC05 EA02 EA05 4J027 AC03 AC06 AJ08 BA03 BA06 BA07 BA08 BA09 BA14 BA15 CB10 CC05 CC06 CD04 CD08

Claims (4)

[Claims] An ophthalmic lens is immersed in an aqueous solution containing a hydrophilic monofunctional photopolymerizable monomer and a hydrophilic polyfunctional photopolymerizable monomer, and irradiated with ultraviolet light. Method. 2. The method according to claim 1, wherein the hydrophilic monofunctional photopolymerizable monomer is (methoxy) polyethylene glycol mono (meth) acrylate. 3. The method according to claim 1, wherein the hydrophilic polyfunctional photopolymerizable monomer is polyethylene glycol di (meth) acrylate. 4. A hydrophilic ophthalmic lens obtained by the hydrophilic treatment method according to claim 1. Description: