JPH0777672A - Soft contact lenses - Google Patents

Abstract

(57) [Summary] [Structure] The soft contact lens according to the present invention is a composition obtained by copolymerizing a hydrophilic monomer, a silicon-containing (meth) acrylate, and a specific fluorine-containing compound. [Effect] It has excellent oxygen permeability, has sufficient mechanical strength and is not easily damaged by handling the lens such as cleaning. In addition, since it is less likely to be contaminated by a tear fluid component or the like during wearing and bacterial growth is suppressed, it is possible to provide a safe contact lens with less influence on the cornea.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a soft contact lens which is excellent in oxygen permeability and has a large mechanical strength so that the lens is hardly damaged when handling the lens, and a composition thereof. Furthermore, since it contains a silicon-containing (meth) acrylate (hereinafter, acrylate and methacrylate are collectively abbreviated as (meth) acrylate) and a specific fluorine-containing compound, it is unlikely to be contaminated by tear components during wearing, and has durability. It relates to excellent soft contact lenses.

[0002]

2. Description of the Related Art Soft contact lenses have been widely used by people who have not been able to wear conventional hard contact lenses because of their good wearing sensation, but due to recent advances in cleaners and sterilization systems, soft contact lenses have become even more popular. The number of wearers is increasing, and it is spreading at a momentum that approaches the share of hard contact lenses. Most of the materials for soft contact lenses that are currently in widespread use include those containing 2-hydroxyethyl methacrylate as a main component and those containing N-vinyl-2-pyrrolidone as a main component.

It has been generally pointed out that the problems of the soft contact lens are that the lens care is complicated and that the lens is easily damaged when handling the lens. Furthermore, the oxygen permeability depends on the water content, so it is insufficient compared to hard contact lenses, and soft contact lenses are soft and have a good wearing feeling, but because they are flexible, they shape on the cornea during wearing. Also tends to change, and there is a problem in that the expected optical performance cannot be obtained.

Regarding the improvement of mechanical strength, a soft contact lens containing 2,3-dihydroxypropyl methacrylate and methyl methacrylate as main components has been proposed as a material having relatively high rigidity (Japanese Patent Publication No. 62-3245).
No. 6), which is commercially available. On the other hand, with regard to simplification of lens care, some proposals have been made for improvement of stain resistance. For example, Japanese Patent Publication No. 62-62323 discloses:
A soft contact lens containing an alkylene glycol monomethacrylate and a specific fluorine-containing monomer as main components has been proposed.

Further, Japanese Patent Laid-Open No. 63-295611 discloses a soft contact lens containing a silicon-containing (meth) acrylate for the purpose of improving oxygen permeability. Further, Japanese Patent Laid-Open No. 63-293520 discloses a contact lens containing dimethylacrylamide and fluoroalkyl (meth) acrylate as main components, which is excellent in mechanical strength and stain resistance and has improved oxygen permeability. There is.

Further, as a non-hydrous material having high oxygen permeability, a soft contact lens made of a silicone rubber made of polyorganosiloxane has been developed and put on the market. In addition to these, for improving oxygen permeability, for example, JP-A-54-29660 discloses a methacrylate compound containing a hydrophilic group such as a hydroxyl group or a sulfonyl group and a long-chain fluoroalkyl group. Methacrylate compounds possessed are also Japanese Patent Publication No. 60-257
Japanese Patent Publication No. 66 proposes a composition comprising a fluoroalkyl acrylate, an alkyl methacrylate, a small amount of a crosslinking agent and a wetting monomer.

[0007]

Problems with soft contact lenses include weak strength and easy damage, insufficient oxygen permeability and a burden on the cornea, and stains tend to adhere to bacteria and fungi. It is easy to handle, complicated to handle, and easy to change the shape on the cornea during wearing, so that expected optical performance cannot be obtained. Due to these problems, soft contact lenses have a lower prevalence rate than hard contact lenses in spite of a good wearing feeling, and also cause some doubts regarding safety to be proposed. .

Focusing on these problems, as a material having relatively high rigidity and excellent optical performance, Japanese Patent Publication No. 62-3245.
Japanese Patent No. 6 discloses a soft contact lens produced by copolymerization of 2,3-dihydroxypropyl methacrylate and methyl methacrylate. Among the conventional techniques, contact lenses made of a copolymer having 2-hydroxyethyl methacrylate as a main component, which is now widely used, are very flexible and have a good wearing feeling. However, due to its flexibility, the optical surface constantly changes when the eyeball moves or blinks during wearing, and thus the expected optical performance cannot be obtained. When the lens shape changes on the eyeball, it is impossible to correct strong corneal astigmatism, and it may not be possible to obtain appropriate and reliable visual acuity. In this regard, the soft contact lens produced by the copolymerization of 2,3-dihydroxypropyl methacrylate and methyl methacrylate has a relatively high rigidity and therefore has only a small change in the optical surface and has excellent optical performance. However, correction of corneal astigmatism with soft contact lenses has become possible to some extent. However, this contact lens has excellent mechanical strength in the sense of high rigidity, but on the other hand, it has the property that it is difficult to stretch due to the small toughness of the material and it is fragile. Some point out that it is easy to do.

Oxygen permeability is an important factor required for contact lenses. Poor oxygen permeability leads to a lack of oxygen required for the cornea, resulting in hyperemia and prolonged corneal metabolic dysfunction when worn for a long time. Regarding this oxygen permeability, JP-A-63-295
The soft contact lens containing the silicon-containing (meth) acrylate described in Japanese Patent No. 611 has improved oxygen permeability but insufficient strength.

Next, the soft contact lens has a problem that it is easily soiled and the above-mentioned technique is disclosed as a material which is less likely to be soiled, but it is still not sufficient. That is, the composition disclosed in Japanese Examined Patent Publication No. 62-62323 is one in which a fluorine-containing monomer is added to conventionally known 2-hydroxyethyl methacrylate, and the amount of the latter added is 10% by weight depending on the mixing ratio. If it exceeds the percentage, the stain resistance can be improved, but the amount of the fluorine-containing monomer added at that time causes a decrease in the strength of the raw material, and there is a concern that breakage may occur.

As another example, JP-A-54-2
Nos. 9660 and 60-25766 propose compositions containing a hydroxyl group-containing or sulfonyl group-containing hydrophilic methacrylate compound or alkyl methacrylate and a fluorine-containing monomer, and further a small amount of a crosslinking agent and a wetting monomer. However, even in these cases, the strength is insufficient, which is a practical problem. In particular, in the case of a soft contact lens, unlike a hard contact lens, it deforms and adheres along the shape of the cornea of the eye, and therefore oxygen permeability and stain resistance are important, and improvements have been made to this. However, while the oxygen permeability and the stain resistance are improved, it cannot be said that the mechanical strength is practically sufficient.

The advantages and problems of the present soft contact lenses have been described above, but the present invention is aimed at obtaining a soft contact lens having excellent mechanical strength, and has sufficient oxygen permeability. It is an object of the present invention to produce a water-containing soft contact lens which is excellent in stain resistance and has sufficient optical performance. That is, in wearing a soft contact lens, it is possible to obtain a safe contact lens composition that provides sufficient visual acuity correction, has little effect on the cornea, and is not easily damaged during lens handling such as cleaning. It is intended.

[0013]

Means for Solving the Problems That is, the soft contact lens of the present invention comprises the following A, B and C A: hydrophilic monomer B: silicon-containing (meth) acrylate C: fluorine-containing compound represented by the following general formula 1.

[0014]

[Chemical 4]

(In the formula, R ₁ and R ₂ are the same or different groups, and at least one of R ₁ and R ₂ is -C _i.
H _j F _{2i + 1-j represents a} linear or branched fluorine-containing group, i is an integer of 1 to 18, j is an integer of 1 to 2i, and only one is -C _i H _{In the case of j} F _{2i + 1-j} , the other is an essential component which represents an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms or a cycloalkyl group having 3 to 12 carbon atoms). In addition to the above components, methacrylic acid as the D component or hydroxyethyl methacrylate as the E component is an essential component.

Furthermore, the invention is characterized by containing less than 5% by weight of a crosslinking agent in addition to the above essential components.

A more detailed description will be given. Here, the hydrophilic monomer of the component A will be described. This component is the basic skeleton for making soft contact lenses hydrophilic, and since this soft contact lens is a copolymer with highly hydrophobic components such as silicon-containing (meth) acrylate and fluorine-containing compounds, comparison A monomer having a large hydrophilicity is suitable. In particular, N, N-dimethylacrylamide is more hydrophilic than 2-hydroxyethyl methacrylate, which is generally used as a soft contact lens material, and it is possible to obtain the required water content by adding a relatively small amount. Is. Further, the N, N-dimethylacrylamide copolymer is flexible and has high toughness, and the inclusion of this copolymer increases the elongation of the lens and makes it less likely to break. When the amount of this component used is relatively large, the water content of the resulting copolymer is increased and the oxygen permeability is improved, but the mechanical strength and stain resistance are reduced, and the optical performance is also reduced. There is a fear. On the other hand, when the amount used is small, the elongation is small and the feeling of wearing is poor, which is not preferable. The specific amount used is preferably 20 to 80 parts by weight, more preferably 40 to 70 parts by weight.

Next, the silicon-containing (meth) acrylate as the component B will be described. This component is one of the important components for expressing the high oxygen permeability which is one of the objects of the present invention. For example, a compound represented by the following general formula 2 can be given.

[0019]

[Chemical 5]

(Wherein R ₃ is a hydrogen atom or a methyl group, X and Y are organic groups selected from the group consisting of alkyl groups having 1 to 5 carbon atoms, phenyl groups and Z groups, and a is 1 Is an integer of 3 where Z is the following general formula 3
The group represented by )

[0021]

[Chemical 6]

(In the formula, A represents an alkyl group having 1 to 5 carbon atoms, a phenyl group, and b represents an integer of 1 to 5.) Further, a compound having a hydroxyl group in the alkyl group or both ends of a siloxanyl group. Compounds containing a (meth) acrylic group are also useful.

Examples of the silicon-containing (meth) acrylate represented by the above general formula 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 ( Pentamethyldisiloxanyloxy) silylmethyl (meth) acrylate, trimethylsilylethyl (meth) acrylate, pentamethyldisiloxanylethyl (meth) acrylate Methyl bis (trimethylsiloxy) silylethyl (meth) acrylate, tris (trimethylsiloxy) silylethyl (meth) acrylate,
Bis (trimethylsiloxy) (pentamethyldisiloxanyloxy) silylethyl (meth) acrylate, trimethylsiloxybis (pentamethyldisiloxanyloxy) silylethyl (meth) acrylate, tris (pentamethyldisiloxanyloxy) silylethyl ( Meta)
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, 1,3-bis (meth) acryloyloxyethyl-1,1,3,3-tetramethyldisiloxane, 1,3-bis (meth) acryloyloxypropyl-1,1,3, There are 3-tetramethyldisiloxane and the like. Among these, one kind or two or more kinds can be selected and used.

When the amount of this component used is relatively large,
Since the obtained copolymer has increased flexibility and reduced strength, it is easily broken. On the other hand, when the amount used is small, sufficient oxygen permeability cannot be obtained, which is not preferable. The specific amount used is preferably 3 to 50 parts by weight, more preferably 5 to 30 parts by weight.

Subsequently, the fluorine-containing compound as the C component will be described. This component is one of the important components for developing the high oxygen permeability and the stain resistance for the purpose of the present invention. The copolymer using this component is generally said to have improved oxygen permeability and mechanical strength as compared with the copolymer using fluoroalkyl (meth) acrylate.

In the general formula 1, the larger the value of i and the more the number of branches, the higher the oxygen permeability. On the contrary, when i becomes large, the shape stability deteriorates, and when i becomes 19 or more, it is produced. It is difficult to use and cannot be used. Further, when j is large, that is, when the number of fluorine atoms is small, the oxygen permeability is lowered, and when j is 0, the chemical stability of the monomer is deteriorated. Therefore, j is preferably 1 to 2i. Also, only one is
In the case of C _i H _j F _{2i + 1-j} , if the other alkyl group, alkenyl group or cycloalkyl group has 13 or more carbon atoms, the production becomes difficult, and therefore it cannot be used. Examples of the fluorine-containing compound C represented by the general formula 1 include methyl-2,2,2-trifluoroethyl fumarate, methyl-2,2,2-trifluoro-1-trifluoromethylethyl fumarate, Methyl-3,3,4,5,4,5
5,6,6,6-nonafluorohexyl fumarate, allyl-2,2,2-trifluoroethyl fumarate, allyl-2,2,2-trifluoro-1-trifluoromethylethyl 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-trifluoromethylethyl 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, t-butyl-2,2,2-trifluoroethyl fumarate, t-butyl-2,2,2-trifluoro-
1-trifluoromethylethyl fumarate, t-butyl-3,3,4,4,4-pentafluorobutyl fumarate, t-butyl-3,3,4,4,5,5,6,6,6
-Nonafluorohexyl fumarate, t-butyl-3,
3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl fumarate, t-butyl-3,
3,4,4,5,5,6,6,7,7,8,8,9,
9,10,10,10-Heptadecafluorodecyl fumarate, t-butyl-2,2,3,3-tetrafluoropropyl fumarate, t-butyl-2,2,3,3,3
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'-nonafluorohexyl fumarate,
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-
3,3,4,4,5,5,6,6,7,7,8,8,
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
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,
Fumarates such as 2,3,3-tetrafluoropropyl) fumarate and bis (2,2,3,3,4,5,5-octafluoropentyl) fumarate, and corresponding malates can be mentioned. In this case, they can be used alone or as a mixture. At this time, the fluorine-containing compound may be in a cis form or a trans form, but in consideration of homopolymerizability and copolymerizability, fumarate which is a trans form is preferable.

When the amount of this component used is relatively large,
The resulting copolymer may become cloudy and may be easily broken. On the other hand, when the amount used is small, sufficient oxygen permeability cannot be obtained and the stain resistance is also reduced, which is not preferable. The specific amount used is preferably 5 to 50 parts by weight, more preferably 15
~ 40 parts by weight.

Next, methacrylic acid as the component D and 2-hydroxyethyl methacrylate as the component E will be described.
The main components of this soft contact lens are the above A:
The three components are hydrophilic monomer, B: silicon-containing (meth) acrylate, and C: fluorine-containing compound. However, when these components are copolymerized, phase difference occurs depending on the polymerizability of each component, that is, the reactivity ratio. The phenomenon that separation occurs and the copolymer becomes cloudy is observed. This phenomenon is particularly noticeable when a crosslinking component is added to the above-mentioned three components, which is a serious problem in soft contact lenses as optical materials. Methacrylic acid as the D component and 2-hydroxyethyl methacrylate as the E component have been conventionally known as hydrophilic soft contact lens materials, but the copolymerizability is improved by adding this component to the above three components, It has been found that a soft contact lens composition that is uniform and has sufficient transparency as an optical material can be obtained.

It has been found that a relatively small amount of this component is sufficiently effective, but when the amount of this component is relatively large, the water content of the copolymer obtained increases and oxygen content increases. Although the transparency is improved, the mechanical strength and stain resistance may be deteriorated, and further the optical performance may be deteriorated. In particular, D
When the amount of methacrylic acid used as a component is large, the water content increases remarkably and the shape stability is lost, which is not preferable. On the other hand, when the amount used is small, the above-mentioned effects are reduced, which is not preferable. As a concrete usage amount,
0.1 to 30 parts by weight is preferable, and more preferably 0.
5 to 20 parts by weight.

Although the basic components are as described above, it is preferable to use various crosslinking agents in the range of 0.1 to 5 weight percent for the purpose of maintaining the shape of the contact lens and improving the strength. The purpose of the cross-linking agent is to improve the thermal properties of the copolymer and improve the shape stability, and to impart appropriate hardness and elasticity, and to obtain good visual acuity as a contact lens. .

Examples of the cross-linking agent include di- or tri (meth) acrylates of polyfunctional alcohols. Specific examples include ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, and the like.
Di (meth) acrylates such as triethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, butanediol di (meth) acrylate, pentaerythritol di (meth) acrylate,
Further, a polyhydric ester of (meth) acrylic acid with a polyhydric alcohol such as trimethylolpropane or pentaerythritol may be mentioned. More preferably, ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, tetraethylene glycol diacrylate, trimethylolpropane trimethacrylate, pentaerythritol triacrylate, and N, N'-methylenebisacrylamide are used to crosslink the soft contact lens. Suitable as an ingredient. The amount of the cross-linking agent used is preferably 0.1 to 5 weight percent in the polymerizable monomer. If it is less than 0.1% by weight, it becomes difficult to control the water content, which is not preferable. On the other hand, if it exceeds 5% by weight, the oxygen permeability decreases with the decrease in water content, and the flexibility as a soft contact lens also decreases, which is not preferable.

In addition to these, additives such as dyeing agents, colorants, and UV inhibitors, and reactive monomers can be added.

Next, the polymerization of these comonomers will be described. The polymerization is carried out by heating or irradiation with active energy rays such as ultraviolet rays in the presence of a usual polymerization initiator. As a specific polymerization initiator, a radical polymerization initiator is desirable, and for example, benzoyl peroxide, diisopropyl peroxydicarbonate, t-butyl peroxy-2-ethylhexanoate, t-butyl peroxypivalate, t -Butylperoxydiisobutyrate, t-butylperoxyisopropyl carbonate, lauroyl peroxide, azobisisobutyronitrile, azobis (2,4-dimethylvaleronitrile)
Etc. are used. Further, in the case of irradiation with active energy rays, a photopolymerization initiator such as benzoin ether or a sensitizer is used if necessary. The amount of these initiators used is preferably 0.001 to 2 weight percent with respect to the monomers used.

In the contact lens of the present invention, these monomers are injected into a glass tube, a polypropylene tube or a polytetrafluoroethylene tube or a sheet-like void, and heated to cause thermal polymerization, or ultraviolet rays are applied. Irradiation and photopolymerization are suitable. Also,
After that, when distortion occurs in the polymer due to polymerization shrinkage or polymerization heat, it is desirable to perform heat annealing in order to eliminate the distortion. Further, the contact lens thus produced is appropriately swollen by immersing it in a physiological saline solution or the like.

[0035]

The soft contact lens according to the present invention is obtained by copolymerizing a hydrophilic monomer, a silicon-containing (meth) acrylate, and a specific fluorine-containing compound.
It has excellent oxygen permeability and has sufficient mechanical strength so that it will not be easily damaged by handling the lens such as cleaning. Also,
Since the specific fluorine-containing compound is contained, excellent durability and characteristics of being less likely to be contaminated by a tear fluid component or the like during wearing can be imparted. In the present invention, a composition that exhibits these advantages is found.

[0036]

[Examples] The present invention will be described in more detail below with reference to Examples
The present invention is not limited to these.

(Example 1) 58 parts by weight of N, N-dimethylacrylamide, 16 parts by weight of tris (trimethylsiloxy) silylpropyl methacrylate, isopropyl-
25 parts by weight of 2,2,2-trifluoro-1-trifluoromethylethyl fumarate, 1 part by weight of ethylene glycol dimethacrylate, and 0.1 part by weight of azobis (2,4-dimethylvaleronitrile) were mixed well, The mixture was put into a glass tube, the inside was replaced with nitrogen, and deaeration was repeated, and the mixture was sealed under vacuum. This sealed tube was heated in warm water at 30 ° C for 10 hours,
40 ° C for 5 hours, 50 ° C for 5 hours, 60 ° C for 3 hours, 7
Polymerization was carried out by heating at 0 ° C. for 3 hours and then at 100 ° C. for 2 hours in an atmospheric furnace to obtain a round bar. The obtained rod was cut to obtain a contact lens. This lens was swollen in pure water, washed, and then immersed in physiological saline to absorb a predetermined amount of water, and at the same time, elution of the eluate was completed.
The contact lens thus obtained had a water content of 47%, had a good wearing feeling, had excellent optical performance, and had a breaking strength of 285 g and an elongation of 25 mm and excellent mechanical strength. . In addition, as a result of evaluation of stain resistance, it was found that the adhesion of protein was extremely small as compared with the conventional soft contact lens. Also, the oxygen permeability is 25 × 10 ^-11 ml · cm / cm ² · sec · mm.
It was Hg.

The evaluation method was carried out according to the following criteria.

<Evaluation Criteria> (1) Oxygen Permeability Coefficient (Dk Value) Using a scientific laboratory film oxygen permeability meter manufactured by Rika Seiki Co., Ltd., at 35 ° C. in 0.9 weight percent physiological saline, The thickness and the current value (i ∞) of the samples having different diameters of 12.7 mm were measured. Taking the obtained thickness on the x-axis and n · F · A · Pi∞ on the y-axis, a regression line y = ax + b is obtained by the least square method, and the reciprocal of this gradient (1 / a) is taken as [Dk value]. did. However, here
n is the number of electrons involved in the electrode reaction, F is the Faraday constant,
A is the area of the platinum electrode, and P is the atmospheric pressure.

(2) Water content As described above, after washing with pure water and replacing with physiological saline, several lenses were prepared and the total weight (a) thereof was measured. After substituting with pure water again, it was dried in a vacuum dryer for 72 hours, the total weight (b) of the dried lenses was obtained, and the water content was calculated by the following formula.

Moisture content = (ab) / a × 100 (3) Strength: 0.1 mm in thickness and 8 m in width when hydrated with physiological saline.
A plate-shaped molded product of m was prepared and used as a test piece. This test piece was sandwiched between the upper and lower ends in physiological saline at 10 mm intervals,
It was stretched and the stress at break (break strength) and the distance (elongation) between the fulcrums at that time were measured.

(4) Contamination resistance A contact lens was placed in a physiological saline solution containing 0.5% by weight of egg white lysozyme, left at 60 ° C. for 2 hours, thoroughly washed with physiological saline, and then exposed to ultraviolet rays having a wavelength of 280 nm. The absorbance was measured, and the amount of egg white lysozyme obtained was determined.

Examples 2 to 10 Examples 2 to 10 are shown in Table 1.
Shown in. Polymerization and tests were carried out in the same manner as in Example 1 with the compositions shown in Table 1.

[0044]

[Table 1]

The abbreviations of the monomers in the table are as follows.

DMA: N, N-dimethylacrylamide NVP: N-vinyl-2-pyrrolidone S2MA: pentamethyldisiloxanylmethylmethacrylate S4MA: tris (trimethylsiloxy) silylpropylmethacrylate IPF3-Fu: isopropyl-2,2 2-trifluoroethyl fumarate CHF5-Fu: cyclohexyl-3,3,4,4,4
-Pentafluorobutyl fumarate MA: Methacrylic acid HEMA: 2-Hydroxyethyl methacrylate EGDMA: Ethylene glycol dimethacrylate TMPTMA: Trimethylolpropane trimethacrylate (Comparative Example 1) In Example 1, tris (trimethylsiloxy) silylpropyl methacrylate was completely omitted. A contact lens was obtained in the same manner as in Example 1 except that it was not contained and 16 parts by weight of methyl methacrylate was used instead. In the same manner as in Example 1, immersion in physiological saline was performed to sufficiently absorb water, and at the same time, elution of the eluate was completed. The contact lens thus obtained had a water content of 50% and was excellent in mechanical strength and good in wearing feeling, but was slightly inferior in elasticity and insufficient in oxygen permeability.

(Comparative Example 2) In Example 1, except that isopropyl-2,2,2-trifluoro-1-trifluoromethylethyl fumarate was not contained at all and 25 parts by weight of methyl methacrylate was used instead. In the same manner as in Example 1, a contact lens was obtained. In the same manner as in Example 1, immersion in physiological saline was performed to sufficiently absorb water, and at the same time, elution of the eluate was completed. The contact lens thus obtained had a water content of 48% and a good wearing sensation, but had insufficient oxygen permeability. As a result of the stain resistance test, protein adhesion was slightly observed.

[0048]

The soft contact lens according to the present invention is obtained by copolymerizing a hydrophilic monomer, a silicon-containing (meth) acrylate, and a specific fluorine-containing compound, so that it has excellent oxygen permeability and is suitable for cleaning lenses. It has sufficient mechanical strength and excellent durability that it is not easily damaged by handling. In addition, since it is less likely to be contaminated with tear components during wearing and bacterial growth is suppressed, it can be expected that safety is high.

Claims (9)

[Claims] 1. A soft contact lens comprising the following A, B and C as essential components. A: Hydrophilic monomer B: Silicon-containing (meth) acrylate C: Fluorine-containing compound represented by the following general formula 1 (In the formula, R ₁ and R ₂ are the same or different groups, and
_At least one group of ₁ and R _{2 represents} a linear or branched fluorine-containing group represented by —C _i H _j F _{2i + 1-j} , and i
1-18 integers, j represents an integer of 1～2I, and if only one is _{-C i H j F 2i + 1} -j, the other is 1-1 carbon atoms
2 represents an alkyl group having 2 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms or a cycloalkyl group having 3 to 12 carbon atoms) 2. A soft contact lens comprising the following components A, B, C and D as essential components. A: Hydrophilic monomer B: Silicon-containing (meth) acrylate C: Fluorine-containing compound represented by the following general formula 1 (In the formula, R ₁ and R ₂ are the same or different groups, and
_At least one group of ₁ and R _{2 represents} a linear or branched fluorine-containing group represented by —C _i H _j F _{2i + 1-j} , and i
1-18 integers, j represents an integer of 1～2I, and if only one is _{-C i H j F 2i + 1} -j, the other is 1-1 carbon atoms
2 represents an alkyl group having 2 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms or a cycloalkyl group having 3 to 12 carbon atoms) D: Methacrylic acid 3. A soft contact lens comprising the following components A, B, C and E as essential components. A: Hydrophilic monomer B: Silicon-containing (meth) acrylate C: Fluorine-containing compound represented by the following general formula 1 (In the formula, R ₁ and R ₂ are the same or different groups, and
_At least one group of ₁ and R _{2 represents} a linear or branched fluorine-containing group represented by —C _i H _j F _{2i + 1-j} , and i
1-18 integers, j represents an integer of 1～2I, and if only one is _{-C i H j F 2i + 1} -j, the other is 1-1 carbon atoms
2 represents an alkyl group having 2 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms or a cycloalkyl group having 3 to 12 carbon atoms) E: 2-hydroxyethyl methacrylate 4. The soft contact lens according to claim 1, wherein the soft contact lens contains less than 5% by weight of a crosslinking agent in addition to the essential components. 5. The respective components A, B and C are characterized in that the component A is 40 to 70 parts by weight, the component B is 5 to 40 parts by weight, and the component C is 15 to 50 parts by weight. Item 1. A soft contact lens according to item 1. 6. The components A, B, C and D, wherein the component A is 40 to 70 parts by weight, the component B is 5 to 30 parts by weight, the component C is 15 to 40 parts by weight, and the component D is 0. The soft contact lens according to claim 2, which is 5 to 20 parts by weight. 7. The components A, B, C and E are 40 to 70 parts by weight of the component A, 5 to 30 parts by weight of the component B, 15 to 40 parts by weight of the component C and 0. The soft contact lens according to claim 3, which is 5 to 30 parts by weight. 8. The soft contact lens according to claim 1, 2 or 3, wherein the hydrophilic monomer is N, N-dimethylacrylamide. 9. A cross-linking agent among ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, tetraethylene glycol diacrylate, trimethylolpropane trimethacrylate, pentaerythritol triacrylate and N, N′-methylenebisacrylamide. The soft contact lens according to claim 4, wherein the soft contact lens is one or more crosslinkable monomers selected from the group consisting of: