JPH0651101A - Resin for optical lens - Google Patents

Abstract

PURPOSE:To obtain flexibility and stable UV absorptivity by forming the resin from the oxygen-permeable resin contg. silicon atom and copolymerized with an UV absorbent. CONSTITUTION:The resin consists of an oxygen-permeable resin copolymerized with an UV absorbent and contg. silicon atom and has an oxygen permeability coefficient of >=10X10<11>cm<3>(STP).cm/cm<2>.sec.mmHg. In this optical lens resin, the resin is the polymer of a siloxane having a double bond and a compd. having an acryloyl group copolymerized with the UV absorbent. In this case, the acryloyl group includes a methacryloyl group, the UV absorbent has an acryloyl group in the molecule, and the acryloyl group includes a methacryloyl group. Further, 0.01-10wt.% of the absorbent is copolymerized with the oxygen- permeable resin.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a resin for optical lenses, and more particularly to a resin for optical lenses having oxygen permeability.

[0002]

2. Description of the Related Art As a medical optical lens such as a contact lens or an intraocular lens, one made of synthetic resin has been adopted. Regarding contact lenses, oxygen-permeable contact lenses have been developed that reduce the physiological burden on the cornea and can be worn continuously for a long time. Such an oxygen permeable contact lens is disclosed in, for example, JP-A-58-19.
4014, JP-A-59-28127, JP-A-60-
No. 146219, JP-A-2-198415, JP-A-2-147613 and the like, and generally comprises a polymer resin or copolymer resin of a compound containing a silicon atom such as a siloxane compound.

On the other hand, the intraocular lens is used as a substitute for the lens of a cataract patient and is generally made of polymethylmethacrylate resin. However, since the intraocular lens made of polymethylmethacrylate resin is poor in flexibility, it is necessary to make a relatively large incision in the eyeball during a surgical operation for replacing the lens of a cataract patient. If a large incision is made in the eyeball, irregular sutures or incomplete fusion may occur, which may cause astigmatism or macroscopic aberration. Therefore, as for the intraocular lens, as a flexible one which can be inserted into the eyeball by a small incision, there is provided one made of a resin containing a silicon atom similar to that of a contact lens (for example, JP-A-63-216).
57, JP-A-62-109564).

By the way, 200 to 400 contained in sunlight
It is known that ultraviolet rays having a wavelength in the nm region cause chemical changes in the lens and retina and cause eye damage.
In order to avoid such an obstacle due to ultraviolet rays, US Pat. No. 3,141,869 discloses a spectacle lens in which an ultraviolet absorber is mixed. Also for the above-mentioned contact lens and intraocular lens, it is preferable to mix an ultraviolet absorber in the resin containing silicon atoms in order to protect the crystalline lens and retina from ultraviolet rays.

However, when a contact lens or an intraocular lens is formed by mixing an ultraviolet ray absorbent with an oxygen permeable resin composed of a polymer resin or a copolymer resin of a siloxane compound, the ultraviolet ray agent is eluted or bleeds out. Cheap. Further, the characteristics of the ultraviolet absorber are likely to deteriorate. This is because the glass transition point of silicone is lower than room temperature and the polymer is a rubber-like polymer at room temperature. As a result, the molecular motion of the siloxane region is large in the polymer of the siloxane compound, and the ultraviolet absorber existing in this part is large. It is thought that it is easy to move and disassemble. Therefore, such a problem is particularly likely to occur in the oxygen permeable resin in which the content of the siloxane compound is increased in order to improve the oxygen permeability and the flexibility. The elution, bleed-out and deterioration of the characteristics of the ultraviolet absorber may adversely affect the eyeball and pose a safety problem.

An object of the present invention is to provide a resin for an optical lens, which is capable of forming an optical lens which has oxygen permeability, flexibility, and stable ultraviolet absorption characteristics and is safe for the human body.

[0007]

An optical lens according to the present invention
The resin for use is a copolymer of an ultraviolet absorber and contains silicon atoms.
Consisting of an oxygen-permeable resin containing 10 x 10^-11cm
³(STP) / cm / cm ²・ Sec ・ mmHg or more
It has an oxygen permeability coefficient. For this resin for optical lenses
The oxygen permeable resin may be, for example, a UV absorber.
The polymerized siloxane compound having a double bond and the
It is a copolymer with a compound having a liloyl group. here
Then, the acryloyl group is a concept including a methacryloyl group.
is there. Further, the ultraviolet absorber may be, for example, acryl in the molecule.
It has a loyl group. Here again, the acryloyl group is
This is a concept including a methacryloyl group. In addition, UV absorption
The sorbent is 0.01 to 10% by weight of the oxygen permeable resin.
Have been combined.

The oxygen permeable resin used in the present invention is a polymer or copolymer containing a silicon atom and has an oxygen permeability coefficient of 10 × 10 ^-11 cm ³ (STP) · cm / cm ^2.
・ Sec · mmHg or more. This polymer or copolymer contains a silicon atom in the polymer main chain, side chain or both, and for example, the main component is a polymer containing an organic silane group such as a siloxane bond or a trimethylolsilyl group. It is what Oxygen permeability coefficient is 10 × 10 ^-11 cm ³ (STP) · cm / cm ² ·
When it is less than sec · mmHg, oxygen cannot be sufficiently supplied to the cornea when a contact lens is formed using the resin for optical lenses of the present invention. The oxygen permeability coefficient can be measured by a general method such as an electrode method, a vacuum method, or a pressure method.

The polymer containing a silicon atom is preferably a long-chain polymer in which a silicon atom is contained in the polymer through a siloxane bond in order to obtain good oxygen permeability and flexibility. Specific examples of such a polymer include tris (trimethylsiloxy) silylpropyl methacrylate, polydimethylsiloxane having double bonds at both ends, a homopolymer of a silicon-containing monomer such as a silicone-containing acrylate, a silicone-containing methacrylate, and the above-mentioned various types. Mention may be made of copolymers of monomers with other monomers.

The monomers copolymerizable with the silicon-containing monomer include acrylic monomers, methacrylic monomers,
Monofunctional monomers such as aromatic vinyl monomers and heterocyclic vinyl monomers, diacryl monomers, dimethacryl monomers, triacryl monomers, trimethacryl monomers, tetraacryl monomers, tetramethacryl monomers, aromatic divinyl monomers, aromatic diallyl monomers, etc. A polyfunctional monomer can be illustrated.

Here, as the acrylic monomer and the methacrylic monomer, alkyl acrylates or alkyl methacrylates such as methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, butyl acrylate and butyl methacrylate,
Acrylic acid, methacrylic acid, hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxybutyl acrylate, hydroxybutyl methacrylate and other hydroxyalkyl acrylates or hydroxyalkyl methacrylates, trifluoroethyl acrylate, trifluoroethyl methacrylate, tetrafluoroethyl acrylate, Examples thereof include halogenated alkyl acrylates such as tetrafluoroethyl methacrylate and the like, halogenated alkyl methacrylates, cycloalkyl acrylates such as cyclohexyl acrylate and cyclohexyl methacrylate, cycloalkyl methacrylates and the like. Of these, when methyl methacrylate is used, an optical lens having good mechanical properties can be obtained. Further, when a fluoroalkyl acrylate or a fluoroalkyl methacrylate is used, an optical lens having good oxygen permeability and mechanical properties can be obtained.

Examples of aromatic vinyl monomers include vinylbenzene, vinylnaphthalene, vinylethylbenzene and the like. Examples of the heterocyclic vinyl monomer include vinylcarbazole, maleimide, maleic anhydride and the like. Among the above-mentioned monomers for copolymerization, an acrylate monomer or a methacrylate monomer is particularly preferable in terms of good copolymerizability and an optical lens having good transparency. Especially methyl acrylate,
When methyl methacrylate, trifluoroethyl acrylate, trifluoroethyl methacrylate, acrylic acid or methacrylic acid is used, an optical lens having good mechanical strength, transparency and oxygen permeability can be obtained.

Among the above-mentioned polyfunctional monomers, examples of the bifunctional acrylic or methacrylic monomer include ethylene glycol diacrylate, ethylene glycol dimethacrylate, diethylene glycol diacrylate, diethylene glycol methacrylate and bisphenol A.
Diacrylate, bisphenol A dimethacrylate,
Examples thereof include ethylene oxide-added bisphenol A diacrylate, ethylene oxide-added dimethacrylate and urethane-modified acrylates or methacrylates thereof, glycerol diacrylate, glycerol dimethacrylate, neopentyl glycol diacrylate, neopentyl glycol dimethacrylate and the like. As the trifunctional acrylic or methacrylic monomer,
Examples thereof include trimethylolpropane triacrylate, trimethylolpropane trimethacrylate, pentaerythritol triacrylate, and pentaerythritol trimethacrylate. Examples of the tetrafunctional acrylic or methacrylic monomer include tetramethylol methane tetraacrylate and tetramethylol methane tetramethacrylate. Examples of the aromatic divinyl compound include o-diallyl phthalate, m-diallyl phthalate, p-diallyl phthalate and the like. Specific examples of other polyfunctional monomers include bismaleimide, allyl acrylate, and allyl methacrylate. It should be noted that allyl acrylate or allyl methacrylate is preferably diacrylate, dimethacrylate, triacrylate, trimethacrylate, tetraacrylate or tetramethacrylate in order to achieve good copolymerizability and to enhance the transparency of the optical lens. In particular,
In order to obtain an optical lens having good mechanical strength and transparency, it is preferable to use triacrylate or trimethacrylate.

Among the above-mentioned oxygen-permeable resins used in the present invention, the most preferable one is a siloxane compound having a double bond and an acryloyl group or methacryloyl which can realize good transparency, oxygen permeability and mechanical strength. It is a copolymer with a compound having a group. When the oxygen-permeable resin is a copolymer of a silicon-containing monomer and another monomer, the composition ratio of the silicon-containing monomer and the other monomer has an oxygen permeability coefficient of 10 × 10 ⁻¹¹ cm ³ (STP).
It is necessary to set it to be cm / cm ² · sec · mmHg or more. Generally, the higher the proportion of silicon-containing monomer, the higher the oxygen permeability coefficient. A preferable range of the ratio of the silicon-containing monomer to the other monomer is 10 to 90 parts by weight of the silicon-containing monomer and 9 of the other monomer.
It is 0 to 10 parts by weight. Ratio of silicon-containing monomer is 1
If the amount is less than 0 parts by weight, the required oxygen permeability coefficient cannot be obtained. On the contrary, if it exceeds 90 parts by weight, the mechanical strength is lowered. Ultraviolet absorber An ultraviolet absorber is copolymerized with the above-mentioned oxygen-permeable resin. Since the ultraviolet absorber is thus copolymerized with the oxygen permeable resin, it is unlikely to cause elution, bleed-out and characteristic deterioration.

The ultraviolet absorber used in the present invention is an ultraviolet absorber having an unsaturated bond which is copolymerizable with the oxygen permeable resin, for example, an ultraviolet absorber having a double bond.
As an ultraviolet absorber, it tends to have a bad effect on the eyeball.
A benzotriazole-based, benzophenone-based, salicylate-based, or cyanoacrylate-based UV absorber that can effectively absorb UV in the wavelength range of 0 to 400 nm can be used. Particularly, a benzotriazole-based ultraviolet absorber having a maximum absorption wavelength in the super wavelength region is preferable.

The UV absorber having a double bond is
The thing represented by the following general formula can be illustrated.

[0017]

[Chemical 1]

[0018]

[Chemical 2]

In the above general formula, R ^{1 to} R ⁴ and X ^{1 to} X ⁴ are as follows. R ¹ : hydrogen or a methyl group R ² : hydrogen, a benzyl group or an alkyl group having 1 to 18 carbon atoms. R ^3: hydrogen or an alkyl group having 1 to 18 carbon atoms. R ^4: an alkylene group having 1 to 18 carbon atoms. X ¹ : hydrogen, an alkyl group having 1 to 8 carbon atoms or an alkoxy group. X ² : hydrogen or halogen. X ^3: a hydrogen, a hydroxyl group or an alkoxy group having 1 to 8 carbon atoms. X ⁴ : Hydrogen, hydroxyl group, carboxyl group or sulfo group.

More specific examples of the ultraviolet absorber having a double bond capable of polymerizing with the oxygen permeable resin include 2-hydroxy-4- (2-methacryloyloxyethoxy) benzophenone and 2- [2'-hydroxy-5. ′-(Β-methacryloyloxyethoxy) -3′-t-butylphenyl] -5-methyl-2H-benzotriazole, 2-
[2′-hydroxy-5 ′-(β-methacryloyloxyethoxy) -3′-t-butylphenyl] -5-chloro-2H-benzotriazole, 2- [2′-hydroxy-5 ′-(β-methacryloyl) Oxyethoxy)-
3'-t-butylphenyl] -5-methoxy-2H-benzotriazole, 2- [2'-hydroxy-5'-
(Β-methacryloyloxyethyl) -3′-t-butylphenyl] -5-methyl-2H-benzotriazole, 2- [2′-hydroxy-5 ′-(β-methacryloyloxyethyl) -3′-t- Butylphenyl] -5
-Chloro-2H-benzotriazole, 2- [2'-hydroxy-5 '-(β-methacryloyloxyethyl)
-3'-t-Butylphenyl] -5-methoxy-2H-
Benzotriazole, 2- [5 '-(β-acryloyloxyethoxy) -2'-hydroxy-3'-t-butylphenyl] -5-methyl-2H-benzotriazole, 2- [5'-(β-acryloyl Oxyethoxy)
-2'-hydroxy-3'-t-butylphenyl] -5
-Chloro-2H benzotriazole, 2- [5 '-(β
-Acryloyloxyethoxy) -2'-hydroxy-
3'-t-butylphenyl] -5-methoxy-2H-benzotriazole, 2- [5 '-(β-acryloyloxyethyl) -2'-hydroxy-3'-t-butylphenyl] -5-methyl- 2H-benzotriazole, 2
-[5 '-(β-acryloyloxyethyl) -2'-
Hydroxy-3′-t-butylphenyl] -5-chloro-2H-benzotriazole, 2- [5 ′-(β-acryloyloxyethyl) -2′-hydroxy-3′-t
-Butylphenyl] -5-methoxy-2H-benzotriazole, 2- [2'-hydroxy-5 '-(β-methacryloyloxyethoxy) phenyl] -5-methyl-
2H-benzotriazole, 2- [2'-hydroxy-
5 '-(β-methacryloyloxyethoxy) diphenyl] -5-chloro-2H-benzotriazole, 2-
[2′-Hydroxy-5 ′-(β-methacryloyloxyethoxy) diphenyl] -5-methoxy-2H-benzotriazole, 2- [3- (2H-benzotriazol-2-yl) -5- (1,1 -Dimethylethynyl)-
4-Hydroxyphenoxy] ethyl-2-methyl-2-
Propenoate, 2- [3- (2H-benzotriazol-2-yl) -5- (1,1-dimethylethynyl)-
4-hydroxyphenoxy] ethyl-2-propenoate, 4-allyloxy-2-hydroxybenzophenone,
2- (5'-n-butyl-2'-hydroxy-3'-methacryloylanomyethylphenyl) -2H-benzotriazole, 2- (2'-hydroxy-3'-methacryloylaminoethyl-5'-n-nonyl Phenyl) -2
H-benzotriazole, 2- (3'-acryloylaminoethyl-5'-n-butyl-2'-hydroxyphenyl) -2H-benzotriazole, 2- (3'-acryloylaminoethyl-2'-hydroxy-5) '-N-
Nonylphenyl) -2H-benzotriazole, 2-
(3'-allyl-2'-hydroxy-5'-n-nonylphenyl) -2H-benzotriazole, 2- (3'-
Allyl-2'-hydroshiki-5'-n-nonylphenyl) -2H-benzotriazole, 2- [2'-hydroshiki-5'-methacryloyloxy-3'-t-butylphenyl] -2H-benzotriazole, 2 -[2'-
Hydroxy-5'-methacryloyloxy-3'-t-
Butylphenyl] -5-chloro-2H-benzotriazole, 2- [5'-acryloyloxy-2'-hydroxy-3'-t-butylphenyl] -2H-benzotriazole, 2- [5'-acryloyloxy- 2'-Hydroxy-3'-t-butylphenyl] -5-chloro-
2H-benzotriazole may be mentioned.

The ultraviolet absorbers may be used alone or in combination of two or more in order to realize more various ultraviolet absorption characteristics. If the above ultraviolet absorber is added together with the raw material monomer during the synthesis of the oxygen permeable resin, the unsaturated bond portion reacts with the raw material monomer and is incorporated into the oxygen permeable resin.

The concentration of the ultraviolet absorber in the oxygen permeable resin varies depending on the purpose of use of the optical lens formed of the resin for optical lenses of the present invention. For example, when the optical lens is used as a contact lens or an intraocular lens, it is preferable to adjust the addition amount so that the transmittance at the maximum absorption wavelength in the ultraviolet region of 200 to 400 nm is less than 20%. This addition amount can be determined in relation to the thickness of the optical lens in addition to the transmittance.

The general concentration of the ultraviolet absorber is 0.01 to 10% by weight based on the weight of the mixed liquid of the raw material monomers of the oxygen permeable resin. If the concentration is less than 0.01% by weight, sufficient UV absorption characteristics cannot be obtained. On the contrary, if the addition amount exceeds 10% by weight, the polymerization rate may be lowered and the mechanical strength may be lowered. Additives Colorants may be added to the resin for optical lenses of the present invention in order to adjust the absorption characteristics of the optical lenses in the visible light region. As the colorant, a direct dye, an oil-soluble dye, an acid dye, a basic dye, a disperse dye, a vat dye or the like is used. In addition, monoazo, bisazo, anthraquinone, quinonaphthalone, xanthene, pyrazole,
Organic dyes such as triphenylmethane-based, indigoid-based, fluorane-based, and quinoline-based dyes may be used. Applications of Resin for Optical Lens The resin for optical lens of the present invention can be molded into a predetermined optical lens shape by a general molding method such as cast polymerization, injection molding, and extrusion molding. The oxygen permeable resin is 3
If it has dimensional crosslinking, cast polymerization is preferred. Further, in order to obtain a predetermined optical lens shape, a desired shape can be formed simultaneously with molding using an appropriate mold. When it is necessary to create a wide variety of shapes such as contact lenses and intraocular lenses, first create a columnar or flat plate-shaped molded product, and then cut this molded product into the desired shape by cutting or polishing. Is preferably formed.

Since the contact lens and intraocular lens obtained by the composition of the present invention are made of an oxygen permeable resin containing silicon atoms, they have good flexibility and oxygen permeability. In addition, the ultraviolet absorber is highly safe because it is unlikely to cause elution, bleed-out and characteristic deterioration.

[0025]

Example 1 A four-necked flask equipped with a stirrer, a thermometer, a reflux condenser, and a nitrogen gas inlet was prepared, and 2,6-diisocyanatocaproic acid-β-isocyanatoethyl was added to the flask. 53.4 parts of ester, 52 parts of 2-hydroxyethyl methacrylate and di-n-butyltin dilaurate of 0.
01 parts were charged, and the mixture was stirred under a nitrogen atmosphere while heating at 50 ° C. until the absorption of hydroxyl groups disappeared in the infrared absorption spectrum.

Next, 94.6 parts of both-terminal-alcohol-modified polydimethylsiloxane having an average molecular weight of 946, represented by the following general formula (1), was added to the above-mentioned flask to obtain an isocyanate group of infrared absorption spectrum. The mixture was stirred under a nitrogen atmosphere while heating at 50 ° C until the absorption disappeared. As a result, a reaction product containing a siloxane macromer as a main component having two double bonds at each end was obtained.

[0027]

[Chemical 3]

Next, to 10 parts of this reaction product, 3 parts of trifluoroethyl methacrylate, 0.055 part of trimethylolpropane trimethacrylate and 0.004 part of azobismethylvaleronitrile were added. Further, 0.25% by weight of 2-hydroxy-4- (2-methacryloyloxyethoxy) benzophenone, which is an ultraviolet absorber, was added to this monomer mixed solution, mixed and dissolved to obtain a uniform transparent stock solution. .

Next, the obtained transparent stock solution was placed in a rod-shaped glass container, the container was replaced with nitrogen, and the container was sealed. This glass container is placed in a constant temperature water bath at 40 ° C for 40 hours at 50 ° C.
-24 hours, 60 ° C-16 hours, 70 ° C-4 hours, 90
The treatment was carried out under 5 conditions of ℃ -2 hours. Then, it was further heated in a circulating dryer at 130 ° C. for 3 hours to obtain a rod-shaped polymer. The obtained polymer had a Shore D hardness of 74 and was good in hardness, machinability and polishability.

The obtained polymer was made into small pieces with a mixer, and 1 g of the small pieces was immersed in 50 g of distilled water and heated at 100 ° C. for 30 hours. Then, when the elution amount of the ultraviolet absorber contained in the distilled water was examined spectroscopically, the elution of the ultraviolet absorber was not confirmed. In addition, the polymer is 17m in diameter
and a disk having a thickness of 5 mm. This disk was heat-treated at 120 ° C. for 16 hours under vacuum reduced pressure, but no change in color tone and absorbance due to bleed-out of the ultraviolet absorber was observed.

Further, the polymer is 9 mm in diameter and 0.2 in thickness.
It was processed into a disc of mm, and the disc was heat-treated at 120 ° C. for 16 hours under vacuum reduced pressure. For this disc, use a fade meter at room temperature for 20
A 0-hour irradiation test was performed. The absorbance after irradiation was 97.6% of the absorbance before irradiation, and it was confirmed that this disc had excellent light resistance.

The oxygen permeation coefficient of the polymer was examined by using a Seikaken-type film oxygen permeation meter and found to be 32 × 10 ⁻¹¹ cm ³ (STP) · cm / cm ² · se at 37 ° C.
It was c · mmHg. Also, the polymer is used in the lens system 9.
0 mm, base curve 8.0 mm, lens power-3.
It was confirmed that it could be processed into a contact lens of 00D and the cutting and polishing property was also good.

As a reference, FIG. 1 shows an ultraviolet-visible absorption spectrum (transmittance) of a disk having a thickness of 0.2 mm used for the light resistance test. As is apparent from FIG. 1, this disk has a sufficiently large absorption characteristic in the ultraviolet region. Example 2 50 parts by weight of tris (trimethylsiloxy) silylpropyl methacrylate, 50 parts by weight of trifluoroethyl methacrylate, 0.05 part by weight of azobisisobutyronitrile, and 0.1 part of azobiscyclohexanecarbonitrile.
A monomer mixture containing 5 parts by weight was prepared. 2- [2'-hydroxy-5 '-(β-methacryloyloxyethyl) as an ultraviolet absorber for this monomer mixture
0.5% by weight of phenyl] -5-methyl-2H-benzotriazole was added and dissolved to obtain a uniform transparent polymerization stock solution.

Next, the obtained polymerization stock solution was sealed in a test tube. Then, the test tube is heated from 60 ° C to 110 ° C for 24 hours.
The temperature was raised over time, and then the temperature was further held at 110 ° C. for 4 hours, whereby a polymer was obtained. With respect to the obtained polymer, the elution amount of the ultraviolet absorbent, the decrease in the absorbance due to the bleed-out of the ultraviolet absorbent, and the light resistance were examined by the same method as in Example 1. No elution of the ultraviolet absorber was observed. The rate of decrease in absorbance due to bleed-out was 0.6%, which was extremely small. Light resistance is
The absorbance after light irradiation is 98.2 with respect to the absorbance before light irradiation.
%, Which was confirmed to be excellent.

The oxygen permeability coefficient of the polymer was measured in the same manner as in Example 1 to find that it was 30 × 10 ^-11 cm ³ at 37 ° C.
(STP) · cm / cm ² · sec · mmHg. In addition, it was confirmed that the polymer can be processed into a contact lens having a lens system of 9.0 mm, a base curve of 8.0 mm, and a lens power of −3.00 D, and has excellent cutting and polishing properties. Example 3 Polydimethylsiloxane 45 having double bonds at both ends
Parts by weight and trifluoroethyl methacrylate 47.5
Parts by weight, 3 parts by weight of methacrylic acid and 4.5 parts by weight of trimethylolpropane trimethacrylate are uniformly mixed, and further 0.05 part by weight of azobisisobutyronitrile and 0.15 part by weight of azobiscyclohexylcarbonitrile. Parts were added.

2- [2'-Hydroxy-5 '-(β-methacryloyloxyethoxy) -3'-t-butylphenyl] -5-methyl-2H-benzotriazole was added to this monomer mixture as an ultraviolet absorber. 0.5
% By weight was added and mixed / dissolved to obtain a uniform transparent stock solution.
The obtained stock solution was placed in a rod-shaped glass container, the inside of the glass container was replaced with nitrogen, and the container was sealed. This glass container 6
Heat from 0 ° C to 110 ° C over 24 hours, then 1
When kept at 10 ° C. for 4 hours, a polymer was obtained. This polymer had a Shore D hardness of 70, and had good hardness, machinability, and polishability.

With respect to the obtained polymer, the elution amount of the ultraviolet absorbent, the decrease in the absorbance due to the bleed-out of the ultraviolet absorbent, the light resistance and the oxygen permeation coefficient were examined in the same manner as in Example 1. No elution of the ultraviolet absorber was observed. The rate of decrease in absorbance due to bleed-out was 1.9%, which was extremely small. Light resistance is
Absorbance after light irradiation is 96.3 with respect to absorbance before light irradiation.
%, Which was confirmed to be excellent. The oxygen permeability coefficient is 130 × 10 ^-11 cm ³ (STP) · cm /
It was cm ² · sec · mmHg.

Further, it was confirmed that the polymer can be processed into a contact lens having a lens system of 9.0 mm, a base curve of 8.0 mm and a lens power of −3.00 D, and the cutting and polishing property is also good. As a reference, FIG. 2 shows an ultraviolet-visible absorption spectrum (transmittance) of a disk having a thickness of 0.2 mm used for the light resistance test. As is clear from FIG. 2, this disc has a sufficiently large absorption characteristic in the ultraviolet region.

Next, the polymer was cut and polished to obtain a lens system of 9.0 mm, a base curve of 7.0 mm, and a lens power.
It was processed into a 3.00D contact lens. This contact lens was continuously worn on 10 Japanese white rabbits for 15 days, and a rabbit eye mucous membrane irritation test was performed according to the Draize method. At this time, the contact lens was worn only on one eye. As a result, even after continuous use for 15 days, corneal opacity / edema, palpebral conjunctival hyperemia / edema, bulbar conjunctival hyperemia / edema, and secretions were mild. The total evaluation by the Draize method is 2.3 for the contact lens-wearing eye and 1. for the non-wearing eye.
It was 6 and it was confirmed that this contact lens has no irritation to the ocular mucosa. Therefore, it was confirmed that the contact lens of this example can be continuously worn safely.

[0040]

The resin for optical lenses according to the present invention comprises an oxygen permeable resin copolymerized with an ultraviolet absorber and containing a silicon atom, and has an oxygen permeability coefficient of 10 × 10 ^-11 cm 2.
^{Since it is 3} (STP) · cm / cm ² · sec · mmHg or more, it is possible to form an optical lens which is safe for the human body and which has both oxygen permeability, flexibility and stable ultraviolet absorption characteristics.

[Brief description of drawings]

FIG. 1 is an ultraviolet-visible absorption spectrum of the disk prepared in Example 1.

2 is an ultraviolet-visible absorption spectrum of the disk prepared in Example 3. FIG.

Claims (4)

[Claims] 1. An ultraviolet absorbent copolymerized with an oxygen permeable resin containing a silicon atom, and having an oxygen permeability coefficient of 10 ×.
10 ^-11 cm ³ (STP) ・ cm / cm ²・ sec ・ m
Resin for optical lens with mHg or more. 2. The oxygen-permeable resin is a copolymer of a siloxane compound having a double bond and a compound having an acryloyl group, which is copolymerized with an ultraviolet absorber.
The resin for an optical lens described in 1. 3. The resin for an optical lens according to claim 1, wherein the ultraviolet absorber has an acryloyl group in its molecule. 4. The resin for an optical lens according to claim 1, wherein the ultraviolet absorbent is contained in the oxygen permeable resin in an amount of 0.01 to 10% by weight.