JPS6250728A - Contact lens - Google Patents

Abstract

PURPOSE:To obtain the titled lens having an excellent effect of reforming a visual acuity and a high oxygen permeability and a less tendency for generating the deposition of a protein etc. and also enabling to wear it continuously for long periods by forming the titled lens from a polymer obtd. by polymerizing a monomer shown by the formula as an essential component. CONSTITUTION:The titled lens is composed of the polymer obtd. by polymerizing the monomer shown by the formula wherein R<1>, R<2> and R<3> are each a methyl, a trimethylsiloxy or a pentamethyldisiloxanyloxy group, (n) is 2 or 3, as the essential component. The contact lens comprising a bis(siloxanylalkyl)fumarate as a main component shown by the formula contains the fumarate monomer having two bulky siloxanyl groups in a molecule, and has a space produced by its substituent in a polymerization, and the effect of a low surface energy of said substituent, thereby obtaining the very high oxygen permeability. And the titled lens having the less tendency for generating the deposition of a stain due to the effect of the low surface energy of the starting material, and enabling to wear it continuously for long periods is obtd.

Description

DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a contact lens that has high oxygen permeability and can be worn continuously for a long period of time.

[Summary of the invention]

The present invention dramatically improves the oxygen permeability coefficient of a contact lens by polymerizing bis(siloxanylalkyl) fumarate as an essential component, thereby making it possible to wear the contact lens continuously for a long period of time.

[Conventional technology]

Contact lenses commonly used today are broadly classified into hard contact lenses and soft contact lenses. Regarding hard contact lenses, recently there has been a shift to lenses whose main component is methyl methacrylate, and
2-33502. Special Publication Showa 56-59450. Special Public Service 1986
Acrylate or methacrylate (hereinafter both acrylate and methacrylate are collectively referred to as acrylate and methacrylate) having a siloxane bond in the side chain as disclosed in 40324 etc.
Contact lenses with improved oxygen permeability made by copolymerizing meth)acrylate and alkyl(meth)acrylate as main components have become mainstream. There are two types of soft contact lenses: water-containing and non-water-containing.
It is a product obtained by copolymerizing a hydrophilic monomer such as vinylpyrrolidone with methyl methacrylate, and the latter is, for example, a product obtained by copolymerizing butyl methacrylate and butyl acrylate.

[Problems and Objectives to be Solved by the Invention] Each of the above contact lenses has both advantages and disadvantages. In other words, hard contact lenses whose main ingredient is polymethyl methacrylate have many advantages, such as excellent vision correction effects, good durability, easy handling, and good machinability. Due to its poor permeability, wearing it for a long time can easily cause physiological damage to the cornea. In addition, contact lenses whose main components are (meth)acrylates and alkyl (meth)acrylates that have cycloxane bonds in their side chains have oxygen permeability coefficients (hereinafter referred to as Dk values) of PMM.
AI7) 0.5X10-”cj・4a/i sec-a
5 x 10-” ~ 40 x 10 compared to m Hf
Although it has been improved to -11, it is still insufficient in terms of long-term wear.

Regarding water-containing soft contact lenses, contact lenses containing 2-hydroxyethyl methacrylate as a main component have a Dk value of 10 x 10 -11 or less, which is insufficient for long-term wear. In addition, the Dk value of contact lenses whose main ingredient is N-viny rubirolidone is 40 to 50X1.
Although the lens has a high mechanical strength of 0""11, its mechanical strength is weak, forcing the lens to be thicker and reducing the effective oxygen permeability coefficient.

In general, water-containing soft contact lenses are prone to deposits of proteins, lipids, and inorganic substances, as well as bacterial growth, and are difficult to maintain, such as daily sterilization by boiling, and are difficult to handle because their mechanical strength is low when they contain water. also requires attention.

On the other hand, non-hydrous soft contact lenses have a Dk value of approximately 10.
~30X10-1'', and although the oxygen permeability has been improved, it is still insufficient in terms of long-term continuous wear.

In general, soft contact lenses have the disadvantage that they lack vision correction effects compared to hard contact lenses.

That is, an object of the present invention is to provide a contact lens that has an excellent vision correction effect, has oxygen permeability that can be worn continuously for a long period of time, and is resistant to deposition of protein, lipids, and inorganic substances.

[Means for solving problems]

That is, the present invention is a contact lens made of a polymer obtained by polymerizing a monomer represented by the general formula CI) as an essential component.

(However, R1, R2 and R3 each independently represent a methyl group, a trimethylsiloxy group or a pentamethyldisi-tetraxanyloxy group, and 5 represents 2 or 5) Bis(siloxane) represented by the general formula CI used in the present invention Specific examples of nylalkyl) 7-malate include bis(trimethylsilylpropyl) 7-malate, bis(pentamethyldisiloxanylpropyl) 7-malate, bis[
Methylbis(trimethylsiloxy)silylpropyl〕7
malate, bis[tris(trimethylsiloxy)silylpropyl] fumarate, bis[tris(hentamethyldisiloxanyloxy]silylpropyl] fumarate, bis[bis(trimethylsiloxy)pentamethyldisiloxanyloxysilylpropyl] fumarate , bis(trimethylsilylethyl) fumarate, bis(pentamethyldisiloxanylethyl) fumarate, bis[methylbis(trimethylsiloxy)silylethyl] fumarate, bis[tris(trimethylsiloxy)silylethyl] fumarate, bis[tris(pentamethyldisiloxy)silylethyl] fumarate, Sanyloxy)silylethyl]7malate, bis[bis(trimethylsiloxy)pentamethyldisiloxanyloxysilylethyl]fumarate, and the like.

Note that bis(siloxanylalkyl)7malate in the present invention can be homopolymerized, but in consideration of the mechanical strength, machinability, and thermal stability of the polymer, it is copolymerized with a small amount of crosslinking component. It is preferable to do so. As the crosslinking component, a polyfunctional polymerizable monomer such as a polyfunctional acrylate, methacrylate, or an allyl compound is used. A specific example is ethylene glycol di(meth)acrylate.

Diethylene glycol di(meth)acrylate.

Examples include triethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, allyl(meth)acrylate, diallyl phthalate, diallyl isoheptalate, diallyl terephthalate, diethylene glycol bisallyl carbonate, triallyl isocyanurate, and the like.

Furthermore, in the present invention, in addition to the above-mentioned bis(siloxanylalkyl) fumarate, it is also possible to copolymerize in a system in which the following monomers are added for the purpose of improving the flexibility of the polymer and the wearing comfort of the lens. . For example, methyl (meth)acrylate,
Ethyl (meth)acrylate, %-butyl (meth)acrylate, vinyl acetate, vinyl propionate, ethyl vinyl ether, butyl vinyl ether, (meth)acrylic acid amide, 2-e-droxyethyl (meth)acrylate, N-vinylpyrrolidone, N -Vinyl oxazolidone, (meth)acrylic acid, glycerol (meth)acrylate, styrene, etc.

In order to polymerize (or copolymerize) the above monomer (system), various commonly used radicals/'L/polymerization initiators are used, but the polymerization behavior of the monomer (system) is It is possible to polymerize (or copolymerize) this 7-termer (system) and mold it into a contact lens using a commonly used method. After (co)polymerizing in a suitable container such as a test tube to obtain a round bar or block, it can be processed into a lens according to the prescription by cutting, polishing, etc. It is also possible to directly mold a contact lens by injecting a monomer containing a polymerization initiator into the created space and polymerizing it in a mold.When polymerizing a large volume, internal strain tends to occur, so the reaction is controlled. However, in order to obtain a uniform material, it is reasonable to use water as a heat medium.

It is also possible to polymerize the above monomers by adding a coloring agent such as a dye or an additive such as an ultraviolet absorber.

Furthermore, the lens surface can be modified by chemically treating the surface of the lens with acid or alkali, or by subjecting it to low-temperature plasma treatment. Furthermore, the wearing comfort can be improved by graft-polymerizing a hydrophilic 7-mer on the surface after low-temperature plasma treatment, or by graft-polymerizing a wood-loving 7-mer on the surface in low-temperature plasma.

[Effect]

Polymers whose main component is bis(siloxanylalkyl) 7-malate have low flexibility because the repeating unit is siloxanylalkoxycarbonylmethylene, and because of the bulky substituents, there is sufficient space inside the polymer. It is thought that this creates gaps and exhibits high oxygen permeability. In addition, it is thought that the effect of lowering the surface energy due to the siloxanyl group further improves the oxygen permeability.

In addition, the siloxanyl group reduces the surface energy of the material, which not only prevents the deposition of proteins, lipids, and inorganic substances on the surface, but also prevents water from penetrating into the lens, preventing proteins, lipids, and inorganic substances from depositing on the surface. It is thought that this can prevent the infiltration of water into the interior of the lens, and prevent the growth of mold and bacteria inside the material.

〔Example〕

The present invention will be described in detail below based on Examples, but the present invention is not limited to these examples. The middle part of the example represents parts by weight.

Example 1 Bis[tris(trimethylsiloxy)silylpropyl]
7 malate aa W t 1.0 part of methyl methacrylate, diethylene glycol dimethacrylate (6 parts of L)
The mixture was thoroughly mixed at 0° C., and 1 part of azobis(2,4-dimethylpaleronitrile) r:L was added and stirred until the mixture was homogeneous. Next, this mixed solution was injected into a glass test tube, the inside of which was purged with nitrogen, and then sealed.

This test tube was immersed in a hot water bath whose temperature was controlled by a program controller at 65°C for 6 hours, at 67°C for 5 hours, and then at 70°C.
Polymerization was carried out by heating for 3 hours at 75°C, 3 hours at 80°C, 2 hours at 85°C, and 2 hours at 90°C to obtain a colorless and transparent round bar. This round bar was cut, and after cutting and polishing, a contact lens was obtained. The oxygen permeability coefficient and stain resistance of the obtained lens were measured by the following method.

(1) Oxygen permeability coefficient (Dk value) MOI manufactured by Xertex Corporation
! ! T, +211o (Multi-range An
a17ffi6r for Disa-olved
The Dk value (CC, cm/all ・1rraHg) was measured on test pieces of 12 diameters and thickness α2+m in α9% physiological saline at 55°C using Oxygen').
I asked for

(11) Stain resistance [L 12 mm in diameter in 2% egg white lysozyme aqueous solution.

A test piece with a thickness of α2m was immersed at 37℃ for 24 hours and the temperature was 280%.
The value of Nff1 was determined from the light absorption in the seaweed.

The resulting Dk value was 4.81 x 10 - - - +mHg, and no dirt was observed.

Example 2 Bis[tris(trimethylsiloxy)silylpropyl 7
malate & 3 parts, vinyl acetate 1. s Part e 2 parts of diethylene glycol dimethacrylate α were mixed well at 60°C, and azobis(2,4-dimethyl mole nitrile) [11
1 part and stirred to make it homogeneous. Subsequently, a contact lens was obtained in the same manner as in Example 1. Dk of the obtained lens
The value is 4.34 x 10 → average・a-/-・current・■Hg,
No dirt was observed.

Example 5 Bis[tris(trimethylsiloxy)silylpropyl 7
1.5 parts of malate & 3 parts (1%-butyl acrylate), 12 parts of diethylene glycol dimethacrylate, 60 parts
After mixing well at ℃, 1 part of t-1 tilpernioxy 2-ethylhexanate (L1 part) was added and stirred to make it homogeneous. Subsequently, a contact lens was obtained by the same procedure as in Example 1. The Dk value of the obtained lens was is 4.92X10 → 匡・cyr/all
- crown/mHg, and no stains were observed as well.

Example 4 A lens was obtained in exactly the same manner as in Example 1 except that N-vinylvinyl resin was used in place of methyl methacrylate. The Dk value of the obtained lens was 4.91
10'cr, -cyt/d-wt·mHg, and no dirt was observed.

Examples & Actual 11 Lenses were obtained in the same manner as in Example 2 except that bis(pentamethylsiloxy)silylpropyl) fumarate was used instead of bis(tris(trimethylsiloxy)silylpropyl) fumarate in Example 2. . The Dk value of the obtained lens is 417 x 10 → C-equipment/-・Ji・■Hg
However, no dirt was observed.

Example & Exactly the same method as in Example 3 except that bis[°tris(pentamethyldisiloxanyloxy)silylethyl]fumarate was used instead of bis[tris(trimethylsiloxy)silylpropyl]fumarate in Example 3. I got the lens. The Dk value of the obtained lens is &79X10→Jin・
cm/di・(8)・KakuHg 1. I dirt/re1 no 1 attachment 4
(1) was not recognized.

〔Effect of the invention〕

As mentioned above, the contact lens of the present invention which is mainly composed of bis(siloxanylalkyl) fumarate has two bulky siloxanyl groups in the molecule of the 7-malate monomer, and is polymerized. In this case, it is thought that very high oxygen permeability is brought about due to the gaps created by the substituents and the effect of the low surface energy of the substituents themselves. Its oxygen permeability is much higher than that of lenses containing siloxanyl methacrylate as a main component, which have been conventionally used as oxygen permeable contact lenses. Additionally, due to the low surface energy of the material, it is difficult for dirt to adhere to the contact lens, making it a contact lens that can be worn continuously for a long period of time.

This material is also expected to be developed into gas separation membranes and medical materials.

that's all

Claims (1)

[Claims] A contact lens characterized by being composed of a polymer obtained by polymerizing the monomer represented by the general formula [I] as an essential component ▲There are mathematical formulas, chemical formulas, tables, etc.▼... [I
] (However, R^1, R^2 and R^3 each independently represent a methyl group, trimethylsiloxy group or pentamethyldisiloxanyloxy group, and n represents 2 or 3)