JPH0815655A - Lens for eye - Google Patents

Abstract

PURPOSE:To provide a lens for eyes having high oxygen permeability, good dynamic characteristics and excellent resistance against contamination. CONSTITUTION:This lens for eyes consists of a polymer containing fluoroalkoxy alkyl(meth)acrylate expressed by formula as the polymer component. In the formula, R<1> us a hydrogen atom or methyl group, R<2> is a 1-20C alkyl group, and R<3> is a >=1C fluoroalkyl group with substitution of one or more fluorine atoms.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an ophthalmic lens having high oxygen permeability and good mechanical properties.

[0002]

2. Description of the Related Art In recent years, polymers having silyl-substituted methacrylates such as tris (trimethylsiloxy) silylpropyl methacrylate and modified polysiloxanes as constituent components have been developed and used as ophthalmic lens materials having high oxygen permeability. JP-A-60-142324 and JP-A-54-24047). In many cases, fluorine-containing monomers (mainly fluorine-substituted alkyl methacrylates) such as trifluoroethyl methacrylate and hexafluoroisopropyl methacrylate are used as copolymerization components in these polymers. The reason why the monomer containing fluorine is used is to improve the oxygen permeability and the antifouling effect, but these effects are due to the proportion of fluorine atoms in the copolymer, that is, in many cases. The ratio tends to increase as the proportion of fluoroalkyl groups) increases.

However, there has been a drawback that an increase in the proportion of fluorine atoms or fluoroalkyl groups causes problems such as increase in creep and increase in hydrophobicity. Further, in order to efficiently increase the proportion of fluorine atoms in the polymer, it is desirable to use a compound having the highest proportion of fluorine, that is, the highest proportion of fluoroalkyl group, but having a long-chain fluoroalkyl group. When the compound is used, since the fluoroalkyl group is rigid, the impact resistance of the polymer is lowered and the polymer becomes brittle.

[0004]

SUMMARY OF THE INVENTION The present invention is intended to solve the above-mentioned drawbacks of the prior art, and provides an ophthalmic lens having high oxygen permeability and excellent mechanical properties and antifouling property. The purpose is to provide.

[0005]

In order to solve the above problems, the present invention has the following constitution.

"An ophthalmic lens made of a polymer containing a fluoroalkoxyalkyl (meth) acrylate represented by the following general formula (I) as a polymerization component.

[0007]

Embedded image (In the formula, R ¹ is a hydrogen atom or a methyl group, R ² is an alkyl group having 1 to 20 carbon atoms, and R ³ is a fluoroalkyl having 1 or more carbon atoms substituted with one or more fluorine atoms. The fluoroalkoxyalkyl (meth) acrylate used in the present invention is characterized in that the fluoroalkyl group moiety R ³ and the alkyl group moiety R ² are linked by an ether bond via oxygen. It is characterized in that various alkyl groups and fluoroalkyl groups can be combined, whereby the degree of freedom in designing a monomer for obtaining a polymer having desired physical properties is extremely wide. Further, since it has an ether bond capable of freely rotating in the molecule, it has an effect of preventing the polymer from becoming brittle, and has a carbon number obtained by adding the carbon number of the alkyl group R ^{2 and} the carbon number of the fluoroalkyl group R ^3. Compared with the case of using a monomer having a single fluoroalkyl group having the same number of carbon atoms, the obtained polymer has a feature that the degree of brittleness is extremely small.

In the fluoroalkoxyalkyl (meth) acrylate represented by the above general formula (I) of the present invention, R ¹ is selected from a hydrogen atom and a methyl group. R ² is selected from an alkyl group having a carbon chain length of 1 or more and 20 or less, and the alkyl group may be linear or branched. Preferred examples thereof include methylene group, ethylene group, trimethylene group, tetramethylene group, pentamethylene group, hexamethylene group, heptamethylene group and octamethylene group.
R ³ has 1 carbon atom substituted with one or more fluorine atoms
The above-mentioned fluoroalkyl groups, examples of which are:
_{(CF 2) 2 H, -CH} 2 CF 3, -CH 2 (CF 2)
_{4 H, CH 2 (CF 2} ) 3 CF 3, -CH (CF 3) 2
And so on. Specific examples of the fluoroalkoxyalkyl (meth) acrylate represented by the general formula (I) obtained by the combination of R ² and R ³ include the following.

[0009]

Embedded image The ophthalmic lens of the present invention is made of a polymer containing a fluoroalkoxyalkyl (meth) acrylate represented by the general formula (I) as a polymerization component, and when the fluoroalkoxyalkyl (meth) acrylate is copolymerized, As the copolymerization component, for example, a monomer conventionally known as a material for an ophthalmic lens can be used without particular limitation. For example, alkyl (meth) acrylates such as methyl (meth) acrylate and ethyl (meth) acrylate, halogenated alkyl (meth) acrylates such as trifluoroethyl (meth) acrylate and tetrafluoroethyl (meth) acrylate, vinylbenzene , Aromatic vinyl monomers such as vinylethylbenzene, and maleimide derivatives such as alkyl-substituted maleimides and fluoroalkyl-substituted maleimides can be used. However, when a siloxane-containing component is used as a copolymerization component, the oxygen permeability of the obtained polymer is improved. Can be improved. The siloxane-containing component used in the present invention may be any as long as it can be copolymerized with the fluoroalkoxyalkyl (meth) acrylate represented by the general formula (I), but silyl-substituted methacrylate, modified polysiloxane, siloxane-substituted maleimide. And a compound selected from siloxane-substituted styrene derivatives can be preferably used. As the siloxane-containing component, a component partially containing a fluorine atom can also be preferably used. Examples of silyl-substituted methacrylates include tris (trimethylsiloxy) silylpropyl methacrylate, tris [(pentamethyldisiloxanyl) oxy] silylpropyl methacrylate, and examples of modified polysiloxanes include diamines at both ends. Examples thereof include heavy bond-modified polydimethylsiloxane. Further, examples of the siloxane-substituted maleimide include the following.

[0010]

[Chemical 4] Moreover, the following can be mentioned as an example of the siloxane-substituted styrene derivative.

[0011]

Embedded image Fluoroalkoxyalkyl (meth) in such polymers
The content of acrylate is not particularly limited, but it is desirable that the content of acrylate is at least 5% by weight or more. If it is less than 5% by weight, the effect of improving the physical properties by using this monomer becomes small.

The ophthalmic lens of the present invention can be manufactured by the following method. A fluoroalkoxyalkyl (meth) acrylate is copolymerized with other copolymerization components as required, and then molded into a lens by cutting, or a functional group that can be modified later with a fluoroalkoxyalkyl (meth) acrylate. It is also possible to copolymerize with a monomer having a group, form a lens, and then modify by a polymer reaction. For soft lenses,
It can also be formed by polymerization in a mold or spin cast polymerization.

Further, in the present invention, in order to protect the eyes from harmful ultraviolet rays and to improve the handling property, an ultraviolet absorber, a dye or a coloring agent may be added to the polymer.

According to the present invention, it is possible to provide an ophthalmic lens having both high oxygen permeability, good mechanical properties and high antifouling property.

[0015]

The present invention will be described below with reference to examples, but the present invention is not limited to these examples.

Example 1 Octafluoropentyloxyethyl methacrylate 5
0 parts by weight, tris (trimethylsiloxy) silylpropyl methacrylate 50 parts by weight and 0.015 parts by weight of ethylene glycol dimethacrylate as a crosslinkable monomer are mixed, and 0.0075 parts by weight of azobisisobutyronitrile and azo are used as a polymerization initiator. After adding 0.0075 parts by weight of biscyclohexanecarbonitrile, it was transferred to a polymerization vessel. The monomer mixture was replaced with an inert gas atmosphere and then sealed, heated at 60 ° C. for 22 hours, heated from 60 ° C. to 110 ° C. over 24 hours, and then held at 110 ° C. for 4 hours. , A polymer was obtained. The obtained polymer was homogeneous and transparent, and had a Shore D hardness of about 20. The oxygen permeability coefficient of this polymer is about 140 × 10 ^-11 cc (STP) cm / cm ² sec.
-MmHg, and it was found that this polymer had good oxygen permeability.

Example 2 50 parts by weight of octafluoropentyloxyhexyl methacrylate, 50 parts by weight of N-3-tris (trimethylsilyloxy) silylpropylmaleimide, and ethylene glycol dimethacrylate 0.0 as a crosslinkable monomer.
After mixing 15 parts by weight and adding 0.0075 parts by weight of azobisisobutyronitrile and 0.0075 parts by weight of azobiscyclohexanecarbonitrile as a polymerization initiator, the mixture was transferred to a polymerization vessel. The monomer mixture was replaced with an inert gas atmosphere and then sealed, first at 60 ° C.
After heating for an hour and then raising the temperature from 60 ° C. to 110 ° C. over 24 hours, the temperature was maintained at 110 ° C. for 4 hours to obtain a polymer. The polymer obtained was soft, homogeneous and transparent. When the Shore A hardness was measured, it was about 35. A disk-shaped sample was cut out from this polymer and the oxygen permeability coefficient was measured to be about 200 × 1.
It was 0 ⁻¹¹ cc (STP) cm / cm ² sec · mmHg, and it was revealed that this polymer had good oxygen permeability.

[0018]

The present invention can provide an ophthalmic lens having high oxygen permeability, good mechanical properties, and antifouling property.

Claims (6)

[Claims] 1. An ophthalmic lens comprising a polymer containing a fluoroalkoxyalkyl (meth) acrylate represented by the following general formula (I) as a polymerization component. Embedded image (In the formula, R ¹ is a hydrogen atom or a methyl group, R ² is an alkyl group having 1 to 20 carbon atoms, and R ³ is a fluoroalkyl having 1 or more carbon atoms substituted with one or more fluorine atoms. Indicates a group.) 2. The ophthalmic lens according to claim 1, wherein the polymer is a copolymer of the fluoroalkoxyalkyl (meth) acrylate and another polymerizable monomer. 3. R ² in the general formula (I) has 2 or more carbon atoms and 12
The ophthalmic lens according to claim 1, wherein the alkyl group is the following, and R ³ is a fluoroalkyl group having 2 or more and 12 or less carbon atoms, which is substituted with 2 or more fluorine atoms. 4. The ophthalmic lens according to claim 2, wherein the polymerizable monomer is a siloxane-containing component. 5. The ophthalmic lens according to claim 4, wherein the siloxane-containing component is one or more compounds selected from silyl-substituted methacrylate, modified polysiloxane, siloxane-substituted maleimide and siloxane-substituted styrene derivative. . 6. The ophthalmic lens according to claim 4, wherein the siloxane-containing component is tris (trimethylsiloxy) silylpropyl methacrylate.