JPH08304746A - Ocular lens material - Google Patents

Abstract

PURPOSE: To provide an ocular lens material which is transparent and is highly resistant to chemicals and has improved oxygen permeability, impact resistance and workability by constituting this lens material of a copolymer of a silicone macromer, fluorine-contg. monomer and specific silicone-contg. styrene monomer. CONSTITUTION: This ocular lens material is composed of the copolymer consisting of the silicone macromer, the fluorine-contg. monomer and the silicone-contg. styrene monomer bonded with silicon atoms directly or via other atoms exclusive of silicon atoms to an arom. ring. The macromer imparts the high oxygen permeability and impact resistance to the copolymer and contains polymerizable groups as represented by acrylic acid groups, methacrylic acid groups and vinyl groups and includes the macromers of >=700 as the number average mol.wt. in terms of styrene at the time of analyzing the mol.wt. of the substantial silicon chains by using a gel permeation chromatograph. The macromer which is expressed by the formula I, II or the formula III and has the polymerizable groups at both ends of the silicon chains in order to decrease the elution component from polymn composition are assure the hardness suitable for working is more preferable.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION This invention relates to ophthalmic lens materials. More specifically, the present invention relates to an ophthalmic lens such as a contact lens, an intraocular lens, etc., which is transparent, has high oxygen permeability and chemical resistance, and is excellent in impact resistance, and particularly relates to an ophthalmic lens material suitable for a contact lens. It is a thing.

[0002]

2. Description of the Related Art Conventionally, polymethylmethacrylate has been used as a material for a hard contact lens because of its excellent optical characteristics, but the material itself has almost no oxygen permeability and is necessary for corneal metabolism. There was a problem that oxygen could not be supplied sufficiently, and when worn for a long time, metabolic disorders of corneal tissues were caused. Therefore, in order to solve such a drawback, as a contact lens, siloxanyl methacrylate or fluoroalkyl methacrylate having excellent oxygen permeability, or a contact lens made of a copolymer thereof is actively used today. However, when a contact lens is made of a material made of these silicone-based monomers or fluorine-based monomers, the strength such as impact resistance tends to decrease, and when the user uses the contact lens, damage or the like is likely to occur. It has been pointed out that (NIKKEI NEWMATERIALS P.57 1
991/9/23).

As a general tendency, in the case of a hard contact lens material, when the silicone type component is increased in order to increase the oxygen permeability, in addition to the decrease in strength as described above,
It is difficult to secure sufficient oxygen permeability when adding other copolymerization components to improve the strength and lens processability because the material hardness decreases and the cutting and polishing processability also decreases. There is a problem that In order to solve such a problem, hitherto, for example, a lens material containing a maleic acid ester or a fumaric acid ester as a copolymerization component (Japanese Patent Laid-Open Nos. 63-11908 and 63-1).
32216), a material containing a silicone-containing acrylic block copolymer (JP-A-4-227616, JP-A-4-249508, etc.), polydimethylsiloxane having trifunctional isocyanate and active hydrogen, and polymerizable. A copolymer material composed of a monomer having a double bond (Japanese Patent Publication No. 3-2283, etc.), a copolymer composed of a silicone-based monomer having a styrene skeleton (JP-A-60-142324, JP-A-2-198415, JP-A-4-120110, and JP-A-4-168415.
Issue, JP-A-4-264421, JP-A-5-456
No. 14, etc.) has been developed.

On the other hand, the ophthalmic lens has one aspect that is easily affected by the environment. For example, the majority of women who use contact lenses are women, but they may be affected by cosmetics. Further, there may occur inconvenience that a patient who cannot avoid using eye drops cannot use the eye drop while wearing the lens. However, there have been no studies of active design of lens materials from the viewpoint of chemical resistance so far, and all the conditions such as strength, processability, oxygen permeability, and chemical resistance are satisfied, and the transparency is excellent. At present, the development of ophthalmic lens materials is desired.

[0005]

DISCLOSURE OF THE INVENTION In view of the above prior art, the present invention provides an ophthalmic lens material which is transparent, has good oxygen permeability, impact resistance and workability and is excellent in chemical resistance. It is intended.

[0006]

[Means for Solving the Problems] As a result of intensive studies to achieve the above-mentioned objectives, the present inventors have found that a silicon-based macromer, a fluorine-containing monomer and an aromatic ring may be directly or with an atom other than a silicon atom. Through the use of a silicon-containing styrene-based monomer in which silicon atoms are bonded via a group, we have succeeded in developing a material that can simultaneously satisfy all physical properties of strength, oxygen permeability, processability, and chemical resistance, and completed the present invention. Came to do.

That is, the present invention is an eye comprising a silicone-based macromer, a fluorine-containing monomer and a copolymer of a silicon-containing styrene-based monomer in which a silicon atom is bonded to an aromatic ring directly or through an atom other than the silicon atom. Lens material for. Hereinafter, the present invention will be described in detail.

Oxygen permeability is compared between silicone macromers, fluorine-containing monomers, and copolymers containing a silicon-containing styrene-based monomer in which a silicon atom is bonded to an aromatic ring directly or through an atom other than the silicon atom as an essential component. Highly transparent, has the transparency and hardness necessary for cutting and polishing, and has an appropriate chemical resistance. Good image formation even after processing into a lens and dipping in 40% ethanol aqueous solution, for example. Can be stably obtained.

The silicone-based macromer used in the present invention imparts high oxygen permeability and impact resistance to the copolymer, and the silicone-based macromer is represented by an acrylic acid group, a methacrylic acid group and a vinyl group. Containing a polymerizable group having a substantial silicone chain molecular weight of 700 or more as a styrene-equivalent number average molecular weight when analyzed by gel permeation chromatography (GPC). In order to sufficiently reduce the amount of eluted components and ensure an appropriate hardness for processing, the structure is represented by the general formulas (1) to (6) having a polymerizable group at both ends of the silicone chain. Macromers are preferred.

[0010]

[Chemical 7]

[0011]

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[0012]

[Chemical 9]

[0013]

[Chemical 10]

[0014]

[Chemical 11]

[0015]

[Chemical 12]

The molecular weight of the silicone macromer is preferably in the range of 1,000 to 10,000, more preferably 2,500 to 5,000. Within this range, physical properties such as oxygen permeability, hardness, processability, and transparency are further improved. The molecular weight of the silicone macromer is determined by hydrolyzing the ester bond contained in the polymer with an acid or the like, and analyzing the substance extracted with an organic solvent such as chloroform using GPC. The styrene-equivalent number average molecular weight. Further, it is possible to specify the chemical structure by fractionating the fraction and performing mass spectrometry (MS), infrared spectroscopic analysis (IR), nuclear magnetic resonance analysis (NMR) elemental analysis, or the like.

In the general formulas (1) to (3), R₁, R_FourIs it
Hydrogen or methyl group, R₂, R₃Each has 1 to 1 carbon atoms
12 alkyl groups or trimethylsiloxy groups,
n₁, n₂, n_Five And n₆Are the same or different 1
Is an integer from 20 to n₃, n_FourAre the same or different
Is an integer of 0 to 20. In the general formulas (4) to (6),
R₁', R₈'Is hydrogen or methyl group, R₂', R ₃',
R_Four', R_Five', R₆'And R₇'Each have 1 to 12 carbon atoms
An alkyl group or a trimethylsiloxy group, R_Four'Ah
R is R_FivePart of 'may be replaced by a fluorine atom
Yes. Protein in tear fluid on the surface of the material due to fluorine substitution
Suppresses contamination with oil, lipids, inorganic components, etc.
It has the effect that it is easy to peel off even if contaminants adhere.
You can expect to have. For example 3,3,3-trifle
Oropropyl group, 1,1,2,2-tetrahydroperf
Ruorooctyl group, 1,1,2,2-tetrahydroper
Fluorodecyl group and the like, among which trifluoro
A propyl group is preferred. Y and Z are 0.01 ≦ Z / Y
It is an integer that satisfies ≦ 1. When Z / Y exceeds 0.5, it becomes
The solubility is poor, so 0.5 or less is desirable.
n₁, n₂, N_Five, And n₆Are the same or different
Is an integer from 1 to 20, and n₃, n_FourAre the same or
Different integers of 0 to 20.

The amount of the silicone macromer unit contained in the copolymer is preferably in the range of 5 to 60%, and more preferably in the range of 10 to 40%, based on the total amount of the copolymer in terms of weight. Preferably there is. These silicone-based macromers may be used alone or in combination of two or more.

Examples of the fluorine-containing monomer used in the present invention include methacrylic acid fluoroalkyl ester, acrylic acid fluoroalkyl ester and fluorine-containing aromatic monomer. Units derived from these monomers have hardness and water-repellent and oil-repellent properties due to the reduction of the critical surface tension due to the fluorine atom. It is possible to suppress contamination with components such as lipids.

Specific examples of the methacrylic acid fluoroalkyl ester and acrylic acid fluoroalkyl ester include trifluoroethyl methacrylate, tetrafluoroethyl methacrylate, tetrafluoropropyl methacrylate, pentafluoropropyl methacrylate, hexafluorobutyl methacrylate and hexafluoroisopropyl methacrylate. , Heptafluorobutyl methacrylate, octafluoropentyl methacrylate, nonafluoropentyl methacrylate, dodecafluoropentyl methacrylate, dodecafluoroheptyl methacrylate, dodecafluorooctyl methacrylate, tridecafluoroheptyl methacrylate and acrylates corresponding to these methacrylates. , Fluorine Specific examples of the organic aromatic monomer, fluorostyrene, trifluoromethyl styrene,
Examples thereof include fluorine-containing styrene derivatives such as pentafluoroethylstyrene, and preferably trifluoroethyl methacrylate, hexafluoroisopropyl methacrylate, otaku fluoropentyl methacrylate, dodecafluorooctyl methacrylate and acrylates corresponding to these methacrylates are used. Further preferably, trifluoroethyl methacrylate, trifluoroethyl acrylate, hexafluoroisopropyl methacrylate and hexafluoroisopropyl acrylate are used. These monomers may be used alone or in combination of two or more.

The amount of the fluorine-containing monomer contained in the copolymer is 1 in terms of weight, based on the total amount of the copolymer.
It is preferably in the range of 0 to 90%, and further 40
It is preferably in the range of -80%. For the fluorine-containing monomer used in the present invention, a combination of pyrolysis gas chromatograph or pyrolysis gas chromatograph and mass spectrometry, pyrolysis gravimetric analysis and mass spectrometry and a combination of gas chromatograph added thereto, for example, elemental analysis, fluorescence It can be analyzed by a composite analysis of other general-purpose analysis methods such as X-ray analysis and nuclear magnetic resonance spectrum.

The silicon-containing styrenic monomer having a silicon atom bonded to the aromatic ring used in the present invention either directly or through an atom other than the silicon atom is generally used as a silicone macromer and acrylic acid having poor compatibility. It has the effect of increasing compatibility with ester- and methacrylic acid-based monomers and hydrophilic monomers, and enabling copolymerization with monomers that impart hardness while maintaining high oxygen permeability without clouding. .

Here, examples of the atom other than the silicon atom include an oxygen atom, a sulfur atom, a nitrogen atom and the like, and among them, an oxygen atom and a sulfur atom are preferable. Examples of the silicon-containing styrene-based monomer in which a silicon atom is bonded to the aromatic ring used in the present invention directly or through an atom other than the silicon atom include a silicon-containing styrene-based monomer represented by the following formula (7). Can be mentioned.

[0024]

[Chemical 13]

Specific examples of the general formula (7) include trimethylsilylstyrene, trimethylsiloxystyrene, (methoxy) dimethylsilylstyrene, (trimethylsiloxy) dimethylsilylstyrene, (trimethylsiloxy).
Dimethylsiloxystyrene, bis (trimethylsiloxy) methylsilylstyrene, bis (trimethylsiloxy) methylsiloxystyrene, tri (trimethylsiloxy) silylstyrene, tri (trimethylsiloxy) siloxystyrene, [di (trimethylsiloxy) methylsiloxy] dimethylsilylstyrene , [Tri (trimethylsiloxy) siloxy] dimethylsilylstyrene, tridecamethylhexasiloxanylstyrene, pentadecamethylheptasiloxanylstyrene, heptadecamethyloctasiloxanylstyrene, nonadecamethylnonasiloxanylstyrene and these A part or all of the methyl group of ethyl group, alkyl group such as tert-butyl, fluoroalkyl group, hydroxyalkyl group, phenyl group, benzyl group and hydroxy group. Examples include silicon-containing styrene-based monomers that are groups and the like, and since the stability of the monomer and the copolymer is good, preferably, a silicon-containing styrene-based monomer in which a silicon atom is directly bonded to an aromatic ring is used, and more preferably Is a silicon-containing styrene-based monomer in which a silicon atom is directly bonded to an aromatic ring containing 6 or less silicon atoms.

One of these monomers may be used, or 2
You may use it in combination of 2 or more types. The amount contained in the copolymer of the silicon-containing styrene-based monomer in which a silicon atom is bonded to the aromatic ring directly or through an atom other than the silicon atom is 1 to 80 relative to the total amount of the copolymer as a weight-converted value. %, More preferably 3 to 5
It is preferably in the range of 0%. When the content of the silicon-containing styrenic monomer in which a silicon atom is bonded to such an aromatic ring directly or through an atom other than the silicon atom is less than the previous range, the obtained ophthalmic lens material has sufficient mechanical strength. In some cases, the workability may be deteriorated, or the white turbidity may occur. When the amount exceeds the above range, sufficient mechanical strength may not be obtained.

The silicon-containing styrenic monomer having a silicon atom bonded to the aromatic ring used in the present invention directly or through an atom other than the silicon atom can be analyzed by the same method as the above-mentioned fluorine-containing monomer. Is. The ophthalmic lens material comprising the copolymer of the present invention preferably has an oxygen permeability of 40 or more, more preferably 50 ( ^10-11 cm ³ · cm / cm ² · sec · mm).
Hg) or higher. The oxygen permeability as used herein is a value measured and obtained by the method shown in the examples of the present specification.

Regarding the mechanical strength, in the falling ball test shown in the examples of the present specification, the height of the falling ball at the time of breakage is preferably 40 cm or more, more preferably 4
It is 5 cm or more. Further, the copolymer used in the present invention is not limited to the above silicone macromers, fluorine-containing monomers, and silicon-containing styrene-based monomers in which a silicon atom is bonded to an aromatic ring directly or through an atom other than a silicon atom. Other copolymerization components can be copolymerized. The copolymerizable monomer contained in the copolymer can be analyzed by the same method as the above-mentioned fluorine-containing monomer.

Examples of the copolymerizable monomer include methacrylic acid alkyl ester and acrylic acid alkyl ester. These monomers may be used directly or on a silicone macromer, a fluorine-containing monomer, an aromatic ring. A silicon-containing styrene-based monomer in which a silicon atom is bonded via an atom other than a silicon atom, etc., is inexpensive as compared with other copolymerization components, and unless the physical properties of the copolymer are impaired, these components are used. Is advantageous in terms of cost, and improvement in mechanical strength can be expected.

Specific examples of these methacrylic acid alkyl ester and acrylic acid alkyl ester include methyl methacrylate, ethyl methacrylate, n-propyl methacrylate, n-butyl methacrylate and tert.
-Butyl methacrylate, isobutyl methacrylate,
n-hexyl amethacrylate, n-octyl methacrylate, n-heptyl methacrylate, n-nonyl methacrylate, n-decyl methacrylate, isodecyl methacrylate, n-lauryl methacrylate, tridecyl methacrylate, n-dodecyl methacrylate, cyclopentyl methacrylate, cyclohexyl methacrylate, Examples thereof include n-stearyl methacrylate and acrylates corresponding to these methacrylates, and preferably methyl methacrylate and methyl acrylate are used. These monomers may be used alone or in combination of two or more.

The amount contained in the copolymer of methacrylic acid alkyl ester and acrylic acid alkyl ester units is
The weight-converted value is preferably 30% or less, more preferably 20%, based on the total amount of the copolymer. Furthermore, surface wettability, lens dimensional stability,
If desired, the monomers described below can be copolymerized to improve mechanical properties and the like.

Examples of the monomer for improving surface wettability include methacrylic acid, acrylic acid, itaconic acid,
2-hydroxyethyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl methacrylate, 2-hydroxypropyl acrylate, glycerol methacrylate, polyethylene glycol methacrylate, N, N'-dimethylacrylamide, N-methylacrylamide, dimethylaminoethyl methacrylate, methylene Examples include bisacrylamide, diacetone acrylamide, N-vinylpyrrolidone, and the like.

The amount of these hydrophilic monomer units contained in the copolymer is 0. It is preferably in the range of 05 to 20%, and more preferably in the range of 0.5 to 10%. As a monomer for improving the dimensional stability of the lens,
For example, ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, polyethylene glycol dimethacrylate, trimethylolpropane trimethacrylate, pentaerythritol tetramethacrylate, bisphenol A dimethacrylate, vinyl methacrylate, acryl methacrylate and the like. The acrylates corresponding to the methacrylates, divinylbenzene, triallyl isocyanurate and the like can be mentioned. These monomers are 1
One kind may be used, or two or more kinds may be used in combination.

The amount of the polyfunctional monomer unit contained in the copolymer is preferably in the range of 0.05 to 15% based on the total amount of the copolymer as a value converted into weight. It is preferably in the range of 0.5 to 10%. Examples of the monomer for improving mechanical properties include aromatic vinyl compounds such as styrene, tert-butylstyrene, 2-methylstyrene, and 4-methylstyrene.

In order to improve the balance of properties such as optical characteristics, oxygen permeability, chemical resistance, strength, dimensional stability in tear fluid and its change over time, the above-mentioned copolymerization is possible. It is preferable to use a plurality of different monomers. The copolymer used as the ophthalmic lens material of the present invention is a method in which a photopolymerization initiator such as benzoin, benzophenone, or benzyldimethylketanol is present in a monomer mixture, and a method of polymerizing by irradiating ultraviolet rays or azobis It can be obtained by a known polymerization method such as thermal polymerization using an azo compound such as isobutyronitrile, benzoyl peroxide or lauroyl peroxide, or an organic peroxide.

[0036]

The present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples. The evaluation method of each physical property is shown below. (1) Oxygen Permeability Coefficient The measurement was carried out in accordance with the method A of JIS-K-7126 except that the measurement temperature was 35 ° C. (2) Ethanol swelling rate Special grade ethanol was put into a sample bottle, and a test piece that was weighed was placed. After soaking for one week, the test piece was weighed exactly one minute after being taken out from the bottle. The change in weight of the test piece was expressed as a percentage and defined as the ethanol swelling rate. (3) Hardness After removing 0.5 mm or more from the surface by cutting, the surface was polished into a mirror surface, and the hardness (Vickers hardness) was measured according to the method described in JIS-Z-2244. (4) Falling ball impact test A disk-shaped sample with a diameter of 12.6 mm and a thickness of 2 mm was set on a table, and a 12φ iron ball (7.04 g) was placed at 15 cm.
It is dropped for the first time, and if not destroyed, the height is increased by 5 cm and the same test is repeated until it is destroyed. The strength was evaluated by the height at which it was broken. (5) Workability evaluation When making a test piece for a falling ball test, it was evaluated by cutting, polishing and processing into a disk shape having a diameter of 12.6 mm and a thickness of 2 mm. The evaluation criteria for the cut surface and the polished surface are shown below.

A: The cutting surface has a gloss A: The polishing surface has a good gloss B: The cutting surface has a gloss, but is slightly opaque B: Polishing unevenness occurs C: The cutting surface becomes white and C: Polished surface becomes white (6) Chemical resistance The manufactured test piece is cut and polished to give a base curve:
A lens of 8.00 mm, lens center thickness: 160 μ, lens power: −3D was prepared, immersed in a 40% ethanol aqueous solution, taken out after a certain period of time, and the change in the base curve immediately after that was evaluated using a contact gauge. The same evaluation was performed using a PMMA lens as a control for evaluation.

[0038]

Example 1 20 parts by weight of silicon-containing styrene represented by the following formula (8) (hereinafter referred to as “parts by weight”), 30 parts of a silicone-based macromer represented by the following formula (9) (Mn3200),
Trifluoroethyl methacrylate (hereinafter 3FM) 40
Parts, methyl methacrylate (hereinafter MMA) 10 parts, methacrylic acid (hereinafter MAA) 5 parts, ethylene glycol dimethacrylate (hereinafter ED) 5 parts, benzyl dimethyl ketal 1 part were charged into a brown bottle and stirred using a mix rotor, Dissolved and mixed. After degassing the mixed solution, in a nitrogen atmosphere, the reaction solution is injected into a cell assembled by two glass plates with a silicone rubber gasket interposed therebetween, and the cell is heated at a temperature of 40 to 50 ° C. UV irradiation was conducted for 1 hour to obtain a transparent copolymer.

Oxygen permeability coefficient, ethanol swelling rate, Vickers hardness, processability and falling ball test were measured for the copolymer thus obtained. The results are shown in Table 1. Further, a contact lens was prepared from the obtained polymer by cutting and polishing, and the chemical resistance was evaluated. The obtained results are shown in Table 2. The copolymer obtained in this example was damaged by a falling ball impact test. Although the impacted part was whitened and cracked, the impact did not propagate and the material was not broken. The damage conditions of the falling ball impact test in other examples are very similar, and the description will be representatively given in the examples of the present invention.

[0040]

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[0041]

[Chemical 15]

[0042]

Example 2 20 parts of silicon-containing styrene represented by the following formula (10), 30 parts of silicone macromer (Mn4000) represented by the general formula (9), 30 parts of 3FM, M
A transparent polymer was obtained in the same manner as in Example 1 except that 20 parts of MA, 5 parts of MAA, 5 parts of ED and 1 part of benzyl dimethyl ketal were used. The results of measuring the physical properties of the obtained copolymer are also shown in Table 1.

Further, a contact lens was prepared from the obtained polymer by cutting and polishing, and its chemical resistance was evaluated.
The obtained results are shown in Table 2.

[0044]

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[0045]

Example 3 10 parts of silicon-containing styrene represented by the following formula (11), 40 parts of a silicone-based macromer represented by the general formula (9) (Mn2000), 40 parts of hexafluoroisopropyl methacrylate (hereinafter 6FM), MM
A transparent polymer was obtained in the same manner as in Example 1 except that 10 parts of A, 5 parts of MAA, 5 parts of ED and 1 part of benzyl dimethyl ketal were used. The results of measuring the physical properties of the obtained copolymer are also shown in Table 1.

Further, a contact lens was produced from the obtained polymer by cutting and polishing, and its chemical resistance was evaluated.
The obtained results are shown in Table 2.

[0047]

[Chemical 17]

[0048]

Example 4 20 parts of silicon-containing styrene represented by the following formula (12), 30 parts of silicone macromer (Mn6000) represented by the general formula (9), 50 parts of 3FM, MA
A transparent polymer was obtained in the same manner as in Example 1 except that 5 parts of A, 5 parts of ED and 1 part of benzyl dimethyl ketal were used.
The results of measuring the physical properties of the obtained copolymer are also shown in Table 1.
Shown in

Further, a contact lens was prepared from the obtained polymer by cutting and polishing, and its chemical resistance was evaluated.
The obtained results are shown in Table 2.

[0050]

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[0051]

Example 5 20 parts of silicon-containing styrene represented by the general formula (10), 30 parts of silicone macromer (Mn4500) represented by the following formula (13), 40 parts of 3FM,
A transparent polymer was obtained in the same manner as in Example 1 except that 10 parts of MMA, 5 parts of MAA, 5 parts of ED and 1 part of benzyl dimethyl ketal were used. The results of measuring the physical properties of the obtained copolymer are shown in Table 1.

Further, a contact lens was prepared from the obtained polymer by cutting and polishing, and its chemical resistance was evaluated.
The obtained results are shown in Table 2.

[0053]

[Chemical 19]

[0054]

Comparative Example 1 Silicone Macromer (Mn4000) Represented by General Formula (9) 30 Parts, 3FM 50 Parts, MMA
A polymer was obtained in the same manner as in Example 1 except that 20 parts, 5 parts of MAA, 5 parts of ED and 1 part of benzyl dimethyl ketal were used. The results of measuring the physical properties are shown in Table 1. The obtained copolymer is cloudy and cannot be used as a lens.

[0055]

Comparative Example 2 20 parts of silicon-containing styrene represented by the general formula (10), 30 parts of tris (trimethylsiloxy) silylpropyl methacrylate, 50 parts of 3FM, MMA
A transparent polymer was obtained in the same manner as in Example 1 except that 20 parts, 5 parts of MAA, 5 parts of ED and 1 part of benzyl dimethyl ketal were used. The results of measuring the physical properties are shown in Table 1.

The state of damage of the copolymer obtained in this Comparative Example by the falling ball impact test is that the impact propagates around the point to be impacted and cracks run radially around that part.
Further, the obtained copolymer has a remarkably high ethanol swelling rate and is expected to have lower chemical resistance. Further, a contact lens was produced from the obtained polymer by cutting and polishing, and its chemical resistance was evaluated. Table 2 shows the obtained results.
Shown in From this, it is understood that the obtained lens has low chemical resistance.

[0057]

Comparative Example 3 20 parts of silicon-containing styrene represented by the general formula (8), 30 parts of silicone macromer (Mn3200) represented by the general formula (9), 50 parts of MMA, M
A polymer was obtained in the same manner as in Example 1 except that 5 parts of AA, 5 parts of ED and 1 part of benzyl dimethyl ketal were used. The results of measuring the physical properties are shown in Table 1.

The resulting copolymer was cloudy and could not be used as a lens.

[0059]

[Comparative Example 4] Silicone macromer represented by the general formula (9) (Mn6000) 30 parts, 3FM 70 parts, MAA
A polymer was obtained in the same manner as in Example 1 except that 5 parts, 5 parts of ED and 1 part of benzyl dimethyl ketal were used. The results of measuring the physical properties are shown in Table 1. The obtained copolymer is cloudy and cannot be used as a lens.

[0060]

[Table 1]

[0061]

[Table 2]

[0062]

EFFECT OF THE INVENTION The ophthalmic lens material of the present invention has good oxygen permeability, processability, and excellent chemical resistance, and is characterized in that it is resistant to cracking even when subjected to impact, and it is also used in eye drops and cosmetics. Less susceptible to external factors. Therefore, the material produced by the present invention is suitable for ophthalmic materials such as contact lenses and intraocular lenses.

Claims (3)

[Claims] 1. An ophthalmic lens material comprising a silicone-based macromer, a fluorine-containing monomer, and a copolymer comprising a silicon-containing styrene-based monomer in which a silicon atom is bonded to an aromatic ring directly or through an atom other than the silicon atom. 2. The ophthalmic lens material according to claim 1, wherein the silicone macromer is at least one compound selected from the compounds represented by the following formulas (1), (2) and (3). . Embedded image Embedded image Embedded image 3. The ophthalmic composition according to claim 1, wherein the silicone macromer is at least one compound selected from the compounds represented by the following formulas (4), (5) or (6). Lens material. [Chemical 4] Embedded image [Chemical 6]