JP2935119B2 - contact lens - Google Patents

Description

Description: TECHNICAL FIELD The present invention relates to a contact lens having excellent oxygen permeability and shape stability.

<Prior Art> At present, as a generally used contact lens, an oxygen-permeable (hereinafter abbreviated as GP) hard contact lens and a water-containing soft contact lens are known. Although the water-containing soft contact lens is excellent in wearing feeling, the oxygen permeability of the material is insufficient. Therefore, it is conceivable to increase the moisture content of the material in order to increase the oxygen permeability, but clinical results have been reported that it is easy to be contaminated by various bacteria and cause serious complications to the cornea and conjunctiva. I have. On the other hand, GP hard contact lenses are highly evaluated in terms of high oxygen permeability, effect of correcting astigmatism, durability and safety, and are becoming the mainstream of contact lenses. Along with this, research on GP hard contact lenses is also actively conducted, but the GP contact lenses are
The reality is that only oxygen permeability is pursued, and other characteristics required for contact lenses are not sufficient.

For example, contact lenses described in JP-A-62-8769, JP-B-62-61928 and JP-B-63-36646 have good oxygen permeability, but have problems in shape stability and stain resistance. There is. On the other hand, dialkyl fumarate used in JP-A-62-99720 and JP-A-62-212618 has poor copolymerizability and even if copolymerization is possible,
It is very brittle and easily breaks and is dangerous. In addition,
The contact lens disclosed in 61-176909 has a low oxygen permeability and is unsuitable for continuous wearing, which has attracted particular attention in recent years.

<Problems to be Solved by the Invention> It is an object of the present invention to provide a contact lens having characteristics such as oxygen permeability, shape stability, stain resistance, and durability in a well-balanced manner.

<Means for Solving the Problems> According to the present invention, the following general formula (I) (Wherein R ₁ is a hydrogen atom or a methyl group, X ₁ and X ₂ are the same or different groups, And m is an integer of 1 to 3, n and p are integers of 0 to 3), and a silicon-containing compound A represented by the following general formula (II): (Wherein R ₂ and R ₃ are the same or different groups, and at least one of R ₂ and R _{3 is} a linear or branched fluoro group represented by —C _h H _k F _{2h + 1-k)} an alkyl group, h is 2 to 18 integer, k is an integer of 1 to 2 × h, also when only one of the _{-C h H k F 2h + 1} -k, the other is C1-12 A fluorine-containing compound B represented by an alkyl group, an alkenyl group having 2 to 12 carbon atoms or a cycloalkyl group having 3 to 12 carbon atoms) and a monomer component containing a radically polymerizable vinyl monomer. A hard contact lens is provided.

 Hereinafter, the present invention will be described in more detail.

The contact lens of the present invention is obtained by copolymerizing a monomer component containing a specific silicon-containing compound A, a specific fluorine-containing compound B, and a radical polymerizable vinyl monomer, and further a monomer component containing a specific vinyl compound C. It is a copolymer consisting of

The silicon-containing compound A used in the present invention can be represented by the following general formula (I): In the formula, R ₁ is a hydrogen atom or a methyl group, X ₁ and X ₂ are the same or different groups, and a methyl group or Is shown. Or 0 or 1, m represents an integer of 1 to 3, and n and p represent an integer of 0 to 3. In this case, it represents a skeleton length for imparting some hydrophilicity to the polymer, and must be 0 or 1 in order to maintain the strength of the copolymer, and m represents a siloxanyl group and a (meth) acryl group. This is one of the factors that determine the length of the bonding portion, and needs to be an integer of 1 to 3 in order to maintain the stability of the monomer and the strength of the copolymer. That is, when m = 0, the monomer or copolymer is susceptible to hydrolysis, and when it exceeds 3, the strength of the copolymer decreases. The values of n and p are factors that determine the size of the siloxanyl group.
If the amount is more than the above, the degree of polymerization does not increase and the processability of the polymer decreases. Examples of the silicon-containing compound A represented by the general formula (I) include trimethylsilylmethyl (meth) acrylate, pentamethyldisiloxanylmethyl (meth) acrylate, methylbis (trimethylsiloxy) silylmethyl (meth) acrylate, and tris ( Trimethylsiloxy)
Silylmethyl (meth) acrylate, bis (trimethylsiloxy) (pentamethyldisiloxanyloxy) silylmethyl (meth) acrylate, trimethylsiloxybis (pentamethyldisiloxanyloxy) silylmethyl (meth) acrylate, tris (pentamethyldisiloxy) Sanyloxy) silylmethyl (meth) acrylate, trimethylsilylethyl (meth) acrylate, pentamethyldisiloxanylethyl (meth) acrylate, methylbis (trimethylsiloxy) silylethyl (meth) acrylate, tris (trimethylsiloxy) silylethyl (meth) acrylate , Bis (trimethylsiloxy)
Pentamethyldisiloxanyloxy) silylethyl (meth) acrylate, trimethylsiloxybis (pentamethyldisiloxanyloxy) silylethyl (meth) acrylate, tris (pentamethyldisiloxanyloxy) silylethyl (meth) acrylate, trimethylsilylpropyl (Meth) acrylate, pentamethyldisiloxanylpropyl (meth) acrylate, methylbis (trimethylsiloxy) silylpropyl (meth) acrylate, tris (trimethylsiloxy) silylpropyl (meth) acrylate, bis (trimethylsiloxy)
(Pentamethyldisiloxanyloxy) silylpropyl (meth) acrylate, trimethylsiloxybis (pentamethyldisiloxanyloxy) silylpropyl (meth) acrylate, tris (pentamethyldisiloxanyloxy) silylpropyl (meth) Acrylate, 2-
Hydroxy-3-trimethylsilylethoxypropyl (meth) acrylate, 2-hydroxy-3-pentamethyldisiloxanylethoxypropyl (meth) acrylate, 2-hydroxy-3-methylbis (trimethylsiloxy) silylethoxypropyl (meth) acrylate, 2-hydroxy-3-bis (trimethylsiloxy)
(Pentamethylsiloxanyloxy) silylethoxypropyl (meth) acrylate, 2-hydroxy-3-tris (trimethylsiloxy) silylethoxypropyl (meth) acrylate, 2-hydroxy-3-trimethylsiloxybis (pentamethyldisiloxa Nyloxy)
Silylethoxypropyl (meth) acrylate, 2-hydroxy-3-tris (pentamethyldisiloxanyloxy) silylethoxypropyl (meth) acrylate,
2-hydroxy-3-trimethylsilylpropyloxypropyl (meth) acrylate, 2-hydroxy-3-
Pentamethyldisiloxanylpropyloxypropyl (meth) acrylate, 2-hydroxy-3-methylbis (trimethylsiloxy) silylpropyloxypropyl (meth) acrylate, 2-hydroxy-3- (bis) (trimethylsiloxy) (pentamethyl Disiloxanyloxy) silylpropyloxypropyl (meth) acrylate, 2-hydroxy-3-tris (trimethylsiloxy) silylpropyloxypropyl (meth) acrylate, 2-hydroxy-3-trimethylsiloxybis (pentamethyldisiloxa) Nyloxy) silylpropyloxypropyl (meth) acrylate, 2-hydroxy-3-tris (pentamethyldisiloxanyloxy)
Silylpropyloxypropyl (meth) acrylate,
Dimethyl (triphenylsiloxy) silylpropyl (meth) acrylate and the like.

The fluorine-containing compound B used in the present invention can be represented by the following general formula (II): In the formula, R ₂ and R ₃ are the same or different groups, and R ₂ and
Represents a linear or branched fluoroalkyl group at least one group of R ₃ is represented by _{-C h H k F 2h + 1} -k, h is 2 to 18 integer, k is 1 to 2 × h represents an integer;
If only one of the _{-C h H k F 2h + 1} -k, the other is C1-12
An alkyl group, an alkenyl group having 2 to 12 carbon atoms or a cycloalkyl group having 3 to 12 carbon atoms. At this time, the oxygen permeability increases as the value of h increases and as the number of branches increases, but conversely, as h increases, the shape stability decreases, and when h is 19 or more, manufacturing becomes difficult. I can not use it. When k is large, that is, when F (fluorine atom) decreases, oxygen permeability decreases. When k is 0, the chemical stability of the monomer deteriorates.
It is. Further, only one of the case of _{-C h H k F 2h + 1} -k, can not be used because the other alkyl group, carbon number of the alkenyl group and the cycloalkyl group production becomes difficult when it is 13 or more. Examples of the fluorine-containing compound B represented by the general formula (II) include, for example, methyl-2,2,2-trifluoroethyl fumarate, methyl-2,2,2-trifluoro-1-
Trifluoromethylethyl fumarate, methyl-3,3,4,
4,5,5,6,6,6-nonafluorohexyl fumarate, allyl (2,2,2-trifluoroethyl) fumarate, allyl (2,2,2-trifluoro-1-trifluoromethyl) ethyl Fumarate, allyl-3,3,4,4,5,5,6,6,6-nonafluorohexyl fumarate, isopropyl-2,2,2-trifluoroethyl fumarate, isopropyl (2,2,2 −
(Trifluoro-1-trifluoromethyl) ethyl fumarate, isopropyl-3,3,4,4,4-pentafluorobutyl fumarate, isopropyl-3,3,4,4,5,5,6,6,6 -Nonafluorohexyl fumarate, isopropyl-3,3,4,
4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl fumarate, isopropyl-3,3,4,4,5,5,6,6,7,7,8 , 8,9,9,
10,10,10-heptadecafluorodecyl fumarate, isopropyl-2,2,3,3-tetrafluoropropyl fumarate, isopropyl 2,2,3,3,4,4,5,5-octafluoropentyl fumarate Tert-butyl-2,2,2-trifluoroethyl fumarate, tert-butyl-2,2,2-
Trifluoro-1-trifluoromethylethyl fumarate, tertiary butyl-3,3,4,4,4-pentafluorobutyl fumarate, tertiary butyl-3,3,4,4,5,5,6, 6,
6-nonafluorohexyl fumarate, tertiary butyl-3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl fumarate, tertiary butyl-3 , 3,4,4,5,5,6,
6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl fumarate, tert-butyl-2,2,3,3-tetrafluoropropyl fumarate, tert-butyl-2 , 2,3,3,4,
4,5,5-octafluoropentyl fumarate, 2-ethylhexyl-2 ',-2',-2'-trifluoroethyl fumarate, 2-ethylhexyl-2 ',-2',-
2'-trifluoro-1'-trifluoromethylethyl fumarate, 2-ethylhexyl-3 ', 3', 4 ', 4',
4'-pentafluorobutyl fumarate, 2-ethylhexyl-3 ', 3', 4 ', 4', 5 ', 5', 6 ', 6', 6'-nonafluorohexylsulfumarate, 2-ethylhexyl −
3 ', 3', 4 ', 4', 5 ', 5', 6 ', 6', 7 ', 7', 8 ', 8',
8'-tridecafluorooctyl fumarate, 2-ethylhexyl-3 ', 3', 4 ', 4', 5 ', 5', 6 ', 6', 7 ',
7 ', 8', 8 ', 9', 9 ', 10', 10 ', 10'-heptadecafluorodecyl fumarate, 2-ethylhexyl-2',
2 ', 3', 3'-tetrafluoropropyl fumarate, 2
-Ethylhexyl-2 ', 2', 3 ', 3', 4 ', 4', 5 ', 5'
-Octafluoropentyl fumarate, cyclohexyl-2,2,2-trifluoroethyl fumarate, cyclohexyl-2,2,2-trifluoro-1-trifluoromethylethyl fumarate, cyclohexyl-3,3,4,4 , 4-Pentafluorobutyl fumarate, cyclohexyl-3,3,4,
4,5,5,6,6,6-nonafluorohexyl fumarate, cyclohexyl-3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl Fumarate, cyclohexyl-3,3,4,4,
5,5,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl fumarate, cyclohexyl 2,2,3,3-tetrafluoropropyl fumarate, cyclohexyl 2,2,3,3,4,
4,5,5, -octafluoropentyl fumarate, bis (2,
2,2-trifluoroethyl) fumarate, bis (2,2,2-
Trifluoro-1-trifluoroethyl) fumarate,
Bis (3,3,4,4,4-pentafluorobutyl fumarate,
Bis (3,3,4,4,5,5,6,6,6-nonafluorohexyl) fumarate, bis (3,3,4,4,5,5,6,6,7,7,8, 8,8-tridecafluorooctyl) fumarate, bis (3,3,4,4,5,5,5,
6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl) fumarate, bis (2,2,3,3-tetrafluoropropyl) fumarate, bis (2,2 And fumarate such as 3,3,4,4,5,5-octafluoropentyl) fumarate and the corresponding malate. When used, they can be used alone or as a mixture. At this time, the fluorine-containing compound may be either a cis form or a trans form, but in view of homopolymerizability and copolymerizability,
Fumarate, which is a trans form, is preferred.

The radically polymerizable vinyl monomer used in the present invention can be selected according to the properties expected of the obtained copolymer. For example, the radically polymerizable vinyl monomer which enhances the shape stability and heat resistance of the copolymer and imparts abrasiveness is provided. As the vinyl monomer, a polyfunctional vinyl monomer is preferable, and specifically, for example, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate Acrylate, dipropylene glycol di (meth) acrylate, trimethylolpropane tri (meth) acrylate, diallyl phthalate, diallyl isophthalate, diallyl terephthalate, vinyl (meth) acrylate, allyl (meth) acrylate, diethylene glycol Over bis allyl carbonate, 2 Arirokishiechiru (meth) acrylate, triallyl trimellitate, triallyl cyanurate, triallyl isocyanurate, divinyl benzene, divinyl adipate and the like.

Further, as a radical polymerizable vinyl monomer for improving the water wettability of the obtained copolymer, for example,
(Meth) acrylic acid, 2-hydroxyethyl (meth) acrylate, (meth) acrylamide, N, N-dimethylacrylamide, N-vinyl-2-pyrrolidone, acryloylmorpholine and the like. Furthermore, other than the above, for example, styrene, p-methylstyrene, o-chlorostyrene, p-chlorostyrene, vinyl acetate, vinyl propionate, vinyl pivalate, ethyl vinyl ether, n-
Butyl vinyl ether, vinyl pyridine and the like can also be used.

In the present invention, the blending ratio of the essential monomer component can be determined in consideration of the physical properties of the obtained copolymer.
90% by weight, 90 to 10% by weight of the fluorine-containing compound B and 100 to 100% by weight of the comonomer containing each of the above components are blended in the range of 0.1 to 50 parts by weight, particularly 1 to 30 parts by weight, for the radical polymerizable vinyl monomer. It is desirable. At this time, when the compounding ratio of the silicon-containing compound A is less than 10% by weight and the compounding ratio of the fluorine-containing compound B is less than 10% by weight, the oxygen permeability decreases, and the silicon-containing compound A exceeds 90% by weight. In such a case, if the strength as a contact lens is reduced, and if the fluorine-containing compound B exceeds 90% by weight, water repellency increases, which is not preferable.

In the contact lens of the present invention, one or more of the vinyl compounds C represented by the following general formula (III) can be used as the monomer component in addition to the essential monomer component.

In the formula, R ₄ represents a hydrogen atom or a methyl group, and
R ₅ is an alkyl group having 1 to 12 carbon atoms or an alkenyl group having 2 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms or a group containing an aromatic ring, or —C _h H _k F _{2h + 1-k} A linear or branched fluoroalkyl group. Where h is 2-18
And k is an integer of 1 to 2 × h. In this case, when R ₅ is an alkyl group, an alkenyl group, a cycloalkyl group or a group containing an aromatic ring and has 13 or more carbon atoms, production is difficult. Further, when h and k of the fluoroalkyl group are out of the above range, they cannot be used for the same reason as in the case of the general formula (II). When the vinyl compound C represented by the general formula (III) uses an alkyl group, an alkenyl group, a cycloalkyl group, or a group containing an aromatic ring as R ₅ , the workability and abrasiveness required for a contact lens are used. And the shape stability and heat resistance can be improved. Specifically, for example, preferred are methyl (meth) acrylate, ethyl (meth) acrylate, isopropyl (meth) acrylate, tertiary butyl (meth) acrylate, cyclohexyl (meth) acrylate, and benzyl (meth) acrylate.
When used, they can be used alone or as a mixture. In the case of using the linear or branched fluoroalkyl ants kill group-containing compound as R ₅ can enhance the mechanical strength while reducing the decrease in the oxygen permeability of a contact lens. Specifically, for example, 2,2,2-trifluoroethyl (meth) acrylate, 2,2,2-trifluoro-1-trifluoromethylethyl (meth) acrylate, 3,3,4,4,5,5 5,5-heptafluoropentyl (meth) acrylate, 3,3,4,4,5,5,6,6,6-nonafluorohexyl (meth) acrylate, 3,3,4,4,5,5,6 , 6,7,7,
8,8,8-tridecafluorooctyl (meth) acrylate, 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-hepta Decafluorodecyl (meth) acrylate, 1,1,2,2-tetrahydroperfluorooctadecyl (meth) acrylate, 2,2,3,3-tetrafluoropropyl (meth) acrylate, 2,2,3,3,4 , 4,5,5,6,6,7,7,8,8,9,9, -Hexadecafluorononyl (meth) acrylate, 2,2,3,3,4,4,
5,5,6,6,7,7,8,8,9,9,10,10,11,11-eicosafluoroundecyl (meth) acrylate and the like.

In the present invention, when the vinyl compound C represented by the general formula (III) is used, the content ratio of each monomer component is 10 to 70% by weight of a silicon-containing compound A and 5 to 60% by weight of a fluorine-containing compound B based on all monomers. And vinyl compound C5
Preferably it is in the range of up to 70% by weight. If the content of the silicon-containing compound A is less than 10% by weight, oxygen permeability is reduced, and if it is more than 70% by weight, strength as a lens is undesirably reduced. If the content of the fluorine-containing compound B is less than 5% by weight, the oxygen permeability decreases, and if it exceeds 60% by weight, the water repellency increases, which is not preferable. Further, when the content ratio of the vinyl compound C is less than 5% by weight, the strength is reduced. If the vinyl compound does not contain a fluorine atom and exceeds 70% by weight, the oxygen permeability is greatly reduced, which is not preferable. On the other hand, when the vinyl compound C contains a fluorine atom and exceeds 70% by weight, the water repellency becomes too high, which is not preferable. The content ratio of the radical polymerizable vinyl monomer is, as described above, based on 100 parts by weight of the comonomer containing each of the components.
It is preferable to add 0.1 to 50 parts by weight, particularly 1 to 30 parts by weight.

In the present invention, to prepare a contact lens,
A known preparation method, for example, copolymerizing the monomer component containing a polymerization initiator, or by adding a photosensitizer and irradiating with ultraviolet light, copolymerizing by a method of copolymerizing, etc. For example, by polymerizing or copolymerizing each of the above monomers in a suitable container such as a test tube, and obtaining a round bar or a block, by cutting, grinding or other machining,
A method of processing contact lenses according to the prescription, a method of injecting a monomer containing a polymerization initiator into a space formed by two molds, and directly forming a contact lens by mold polymerization, a polymerization initiator in a rotating container A suitable amount of a monomer component containing is dropped and polymerized or copolymerized as it is to form a lens, or a polymer is produced in advance by a radical polymerization method or the like, and then the polymer is dissolved in an appropriate solvent and cast. And a method of obtaining a contact lens by removing the solvent. In the above-mentioned preparation method, the polymerization initiator used for polymerizing the monomer is selected from one or more of a group consisting of an organic peroxide and an azo compound having a selected 10 hour half-life temperature of 120 ° C. or less. be able to. Examples of the organic peroxide or azo compound include benzoyl peroxide, diisopropyl peroxydicarbonate, t-butylperoxy-2-ethylhexanoate, t-butylperoxypivalate, t-butylperoxydiisobutyrate, Lauroyl oxide, azobisisobutyronitrile,
Azobis (2,4-dimethylvaleronitrile) and the like are preferred. The amount of the polymerization initiator used is preferably 10 parts by weight or less, more preferably 5 parts by weight or less, based on 100 parts by weight of the raw material monomer.

In the above-mentioned preparation method, the conditions for copolymerizing each monomer may be such that the polymerization system is appropriately replaced with an inert gas such as nitrogen, carbon dioxide, helium, or the like, or under an atmosphere or under degassing conditions. Preferably, the temperature at the time of copolymerization varies depending on the type of polymerization initiator used, but is preferably in the range of 30 to 120 ° C. The total time required for the polymerization is desirably about 10 to 96 hours.

It is also possible to add a coloring agent such as a dye or an additive such as an ultraviolet absorber to the raw material monomer to carry out polymerization.

In the present invention, the contact lens obtained by the above-mentioned preparation method can be subjected to an acid or alkali treatment or a low-temperature plasma treatment to perform a surface modification. The feeling of wearing can also be improved by performing graft polymerization of a hydrophilic monomer by low-temperature plasma treatment or the like.

<Effect of the Invention> The contact lens of the present invention is obtained by copolymerizing a silicon-containing compound B having a saturated fluorine alkyl group, a silicon-containing compound A having a siloxanyl group, and a radically polymerizable vinyl monomer as essential components. In addition, it is possible to obtain a contact lens having the required properties such as oxygen permeability, shape stability, anti-contamination property and durability in a well-balanced manner, and to further reduce the decrease in oxygen permeability by adding a vinyl compound C. In addition, the processability and the polishing property of the contact lens can be further improved, and the heat resistance and the mechanical strength can be increased. Therefore, in the contact lens of the present invention, problems such as shape stability and water wettability, which have been deficient in the high oxygen permeable contact lens, are solved, and further application to a high-performance contact lens is expected.

<Examples> Hereinafter, the present invention will be described in more detail with reference to Examples.
The present invention is not limited to these.

 In the examples, parts represent parts by weight.

Example 1 Tris (trimethylsiloxy) silylpropyl methacrylate 45 parts, isopropyl-2,2,2-trifluoro-
Azobis (2,4-dimethylvaleronitrile) 1 was added to 40 parts of 1-trifluoromethylethyl fumarate, 8 parts of diethylene glycol dimethacrylate and 7 parts of methacrylic acid.
The mixture was mixed well, and the mixture was placed in a glass sealed tube, the inside of which was repeatedly purged with nitrogen, degassed, and sealed under vacuum. The sealed tube is heated at 40 ° C for 10 hours, at 45 ° C for 5 hours, and at 55 ° C for 3 hours.
The mixture was heated at 70 ° C. for 3 hours, and further heated in an air furnace at 90 ° C. for 2 hours and at 100 ° C. for 10 hours to carry out polymerization to obtain a round bar.
The obtained round bar was cut, cut and polished to obtain a contact lens. Table 1 shows the charged amount of each monomer. Next, various physical properties of the obtained contact lens were measured by the following methods. Table 2 shows the results.

Oxygen Permeability Coefficient Xertex Corporation product name "Model 2110" (Multirange Do & Temperature Ana
lyzer) and measured at 35 ° C. in a 0.9% by weight physiological saline solution for a test piece having a diameter of 12.7 mm and a thickness of 0.2 mm, and the DK value (cc)
Cm / cm ² · sec · mmHg).

Stain resistance A test specimen with a diameter of 12.7 mm and a thickness of 0.2 mm was immersed in a 0.5 wt% saline solution of egg white lysozyme.
The absorbance at nm was measured to determine the amount of egg white lysozyme attached.

Vickers hardness Measured with a Terasawa MM-2 type ultra-micro hardness meter manufactured by Taiyo Tester Co., Ltd.

Contact angle The contact angle was measured by a water bubble method using a CA-D contact angle meter manufactured by Kyowa Kagaku Co., Ltd.

Mechanical strength In accordance with JIS K7203 hard plastic bending test method, mechanical strength was measured using a separately polymerized plate sample having a thickness of 2 mm, a length of 50 mm, and a width of 10 mm.

Shape stability A contact lens with a base curve of 7.8 mm, a diameter of 9.0 mm, a center thickness of 0.15 mm, and a power of -3.0 diopter (D) is made, and changes in shape and power before and after immersion in saline at 50 ° C for 4 weeks. It was measured. Base curve change ± 0.
02mm or less, diameter change ± 0.2mm or less, center thickness change ± 0.0
A pass was judged when all the standards of 01 mm or less and the power change of ± 0.10D or less were satisfied.

Example 2 45 parts of methylbis (trimethylsiloxy) silylpropyl methacrylate, isopropyl-3,3,4,4,5,5,6,6,7,
35 parts of 7,8,8,9,9,10,10,10-heptadecafluorodecyl fumarate, 10 parts of vinyl methacrylate and 10 parts of methacrylic acid are mixed well with 1 part of benzoyl peroxide, and this mixture is made of glass. It was put in a sealed tube, the inside was replaced with nitrogen, and degassing was repeated, followed by sealing under vacuum. The sealed tube was heated at 70 ° C. for 24 hours, and further heated at 100 ° C. for 2 hours to perform polymerization.
I got a round bar. The obtained round bar was cut, cut and polished to obtain a contact lens.

Table 1 shows the charged amount of each monomer. Next, various physical properties of the obtained contact lens were measured in the same manner as in Example 1. Table 2 shows the results.

Examples 3 to 60 and Comparative Examples 1 to 7 In the same manner as in Example 2 except that various starting monomers shown in Table 1 were used as the radical polymerization initiator shown in Table 1, benzoyl peroxide was used. Polymerization was carried out in the same manner as in Example 1 to obtain a contact lens. Table 1 shows the charged amount of each monomer. Next, various physical properties of the obtained contact lens were measured in the same manner as in Example 1. Table 2 shows the results.
Shown in

──────────────────────────────────────────────────続 き Continuing on the front page (72) Inventor Atsushi Kawashima 3-3-5 Yamato, Suwa City, Nagano Prefecture Inside SEIKO EPSON Corporation (72) Inventor Satoshi Kubota 3-3-5 Yamato, Suwa City, Nagano Prefecture Say Inside Koepson Corporation (72) Inventor Yu Egawa 3-3-5 Yamato, Suwa-shi, Nagano Seiko Epson Corporation (56) References JP-A-63-37312 (JP, A) JP-A-63-63 132216 (JP, A) JP-A-63-11908 (JP, A) (58) Fields investigated (Int. Cl. ⁶ , DB name) G02C 7/04

Claims (2)

(57) [Claims] 1. The compound of the general formula (I) (Wherein R ₁ is a hydrogen atom or a methyl group, X ₁ and X ₂ are the same or different groups, And m is an integer of 1 to 3, n and p are integers of 0 to 3), and a silicon-containing compound A represented by the following general formula (II): (Wherein R ₂ and R ₃ are the same or different groups, and at least one of R ₂ and R _{3 is} a linear or branched fluoro group represented by —C _h H _k F _{2h + 1-k)} an alkyl group, h is 2 to 18 integer, k is an integer of 1 to 2 × h, also when only one of the _{-C h H k F 2h + 1} -k, the other is C1-12 A fluorine-containing compound B represented by an alkyl group, an alkenyl group having 2 to 12 carbon atoms or a cycloalkyl group having 3 to 12 carbon atoms) and a monomer component containing a radically polymerizable vinyl monomer. A hard contact lens, characterized in that: 2. The method according to claim 1, wherein said monomer component further comprises the following general formula (II)
I) (Wherein R ₄ represents a hydrogen atom or a methyl group;
R ₅ is an alkyl group having 1 to 12 carbon atoms or an alkenyl group having 2 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms or a group containing an aromatic ring, or —C _h H _k F _{2h + 1-k} A linear or branched fluoroalkyl group. Where h is 2-18
The hard contact lens according to claim 1, wherein one or two or more kinds of vinyl compounds C represented by the following formula (1) are represented by the following formula: