JPS62296118A - Contact lens - Google Patents

Abstract

PURPOSE:To improve oxygen permeability and to provide resistance to stain sticking to a titled lens by forming the lens of a (co)polymer contg. a specific compd. as the essential component. CONSTITUTION:This contact lens is formed of the polymer of the compd. expressed by the formula or the copolymer of the compd. expressed by the formula and other polymerizable vinyl monomers {e.g.: multifunctional (meth) acrylate}. In the formula, R<1>-R<5> denote a hydrocarbon or fluorohydrocarbon of 1-9C, l denotes 0-3, n denotes 0-7, p, q denote 0, 1, r denotes 1-3 and p+q+r=3. The contact lens having the excellent oxygen permeability and resistance to staining is thus obtd.

Description

DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a contact lens that has good oxygen permeability and is resistant to dirt.

[Conventional technology]

Contact lenses commonly used today can be broadly divided into hard contact lenses and soft contact lenses. Various types of hard contact lenses have been widely known in the past, but the one that has been widely used for a long time is polymethyl methacrylate (PMMA).
This is a hard contact lens whose main component is i. on the other hand,
Soft contact lenses are made of PMMA (2-hydroxyethyl methacrylate) for the purpose of improving the hydrophilicity.
(H,BMA) and N-vinyl-2-pyrrolidone (MVP
) with hydrophilic monomers such as methyl methacrylate (M
It is copolymerized with MA).

In addition, in recent years, research has been actively conducted to improve the 9248 properties of hard contact lenses.
502. Tokuko Sho 56-39450゜ Tokuko Sho 56-403
24 etc., a contact copolymerized with an alkyl acrylate or methacrylate such as MMA (hereinafter, acrylate or methacrylate is referred to as (meth)acrylate f) and (meth)acrylate containing a siloxane bond in the side chain as the main component. A lens is disclosed.

Furthermore, Japanese Patent Publication No. 40806/1983 discloses a contact lens made of an alkyl-substituted styrene, a cross-linked monomer, and a plasticizer, and Japanese Patent Publication No. 182718/1983 discloses a contact lens made of a styrene monomer and bisphenol-A-dimethacrylate. Contact lenses made of polymers have been disclosed, and JP-A-59-214822 discloses contact lenses made of fluorine-containing styrene polymers or copolymers.

[Problem that the invention seeks to solve]

Each of the above contact lenses has both advantages and disadvantages. In other words, the nodal contact lenses containing PMMA as a main component have many advantages, such as excellent vision correction effects, good durability, easy handling, and good absorbency processability. On the other hand, PMMA has poor hydrophilicity, making it uncomfortable to wear, and furthermore, it has poor oxygen permeability, so wearing it for a long time can easily cause physiological damage to the cornea.

On the other hand, although the soft contact lenses achieve the initial purpose of imparting hydrophilic properties and improve the wearing comfort,
If the copolymer of RZMA and MMA retains its polymorphous shape due to water content, the vision correction effect will be reduced and the durability will be poor.Also, the copolymer of RZMA and MMA cannot be said to have sufficient oxygen permeability, so it is necessary to compensate for this. Clinical results have also shown that materials with higher water content are more likely to be contaminated with bacteria and cause serious complications for the cornea and conjunctiva.

In addition, contact lenses are made by copolymerizing alkyl (meth)acrylate and (meth)acrylate, which has siloxane bonds in the side chains, as the main components.

Although they have covered some of the shortcomings of hard and soft contact lenses and have improved somewhat in terms of oxygen permeability, vision correction effect, durability, and ease of handling, they do have some protein deposits. In addition to this, there is a limit to oxygen permeability, making it unsatisfactory for long-term continuous wear. On the other hand, contact lenses made of alkyl-substituted styrene, cross-linked monomers, and plasticizers, and contact lenses made of a copolymer of styrenic single compact and bisphenol-human-dimethacrylate, have low oxygen permeability and are made of fluorine-containing styrene. Contact lenses made of polymers or copolymers do not exhibit sufficient oxygen permeability.

The present invention has been made to solve the problems as described above, and an object thereof is to provide a contact lens that has good oxygen permeability and is resistant to dirt.

Means for Solving Problems c] That is, the present aAh is characterized by being composed of a polymer or copolymer of monomers or comonomers containing the compound represented by the general formula [I] as an essential component (in the formula , R', R"
, R1, R number and Ha each independently have a carbon number of 1
~9 represents a hydrocarbon group or a fluorohydrocarbon group,
j is an integer from 0 to 3; n is an integer from 0 to 7; p and qti are each independently 0"! or 1; r represents an integer from 1 to 3; provided that p-f-q+r=3) .

f compound' represented by general formula (I) used in the present invention
rl, p-siloxanyl styrene, the polymer of which exhibits high oxygen permeability. In the case of 1, the polymerizability and strength of the polymer are significantly reduced, so it is preferably 1 to 9. t and n are numbers related to the length of the siloxane skeleton, and when `` is 8 or more, it is 1 to 9. Since the mechanical strength of the polymer decreases, it is preferably an integer from 0 to 7. On the other hand, ! represents the number of carbon atoms in the methylene chain that connects the benzene ring and the siloxanyl group, but if ! is 4 or more, the polymer Since mechanical strength decreases, 3 or less is preferable.

Although p-siloxanyl styrene in the present invention can be homopolymerized, the mechanical strength of the polymer is limited.

Copolymerization with Ike's polymerizable vinyl monomers is also possible for the purpose of improving machinability, thermal stability, and wearing comfort of lenses. Copolymerizable and polymerizable monomers such as ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, propylene glycol di( (meth)acrylate), 1, 4-
Butanediol di(meth)acrylate, neopentyl glycol di(meth)acrylate.

Polyfunctional (meth)acrylates such as trimethylolpropane tri(meth)acrylate, diallyl phthalate,
Diallyl isophthalate, diallyl terephthalate, triallyl cyanurate, triallyl isocyanurate,
Polyfunctional allyl compounds such as diethylene glycol bisallyl carbonate, polyfunctional vinyl compounds such as allyl(meth)acrylate, methyl(meth)acrylate, ethyl(ly)acrylate, lupropyl(meth)acrylate, i-propyl(meth)acrylate , n-butyl (meth)acrylate, trifluoroethyl (meth)acrylate, hexafluoroinglovir (meth)acrylate), 3,3,4,4.4-pentafluorobutyl (meth)acrylate, methylbis(trimethylsiloxy) ) siliglovir (meth)acrylate, tris(trimethylsiloxy)silylpropyl(meth)acrylate, tris(pentamethyldisiloxanyloxy)silylpropyl(meth)acrylate, 2-hydroxy-3-
Tris(trimethylsiloxy)silylpropyl(meth)
Acrylate, 2-hydroxyethyl (meth)acrylate, glycerol mole (meth)acrylate, etc.
(Meth)acrylate, vinyl esters such as vinyl acetate and vinyl gropionate, vinyl ethers such as ethyl vinyl ether and phthyl vinyl ether, styrene, (meth)
Acrylic acid, (meth)acrylic acid amide, N-viny/L
-2-Bi0+Jton, TobiniA-2-oxazolidone, etc. are mentioned in a row.

In order to polymerize the above monomer (system) (certain VhFi copolymerization), various commonly used radical polymerization initiators are used, and are determined by taking into account the polymerization behavior of the monomer (system). Also, this monomer (system) t-(
To co)polymerize and mold into contact lenses, 1. A commonly used method is possible. 1. (Co)polymerize monomers containing a polymerization initiator in a suitable container such as a test tube, and After obtaining a rod or block, it can be processed into lenses that match the prescription through mechanical processing such as cutting and polishing.

In addition, when polymerizing a large object with zero volume, which can be directly molded into a contact lens by mold polymerization by injecting a monomer containing a polymerization initiator into the space created by two molds, it is necessary to create a strain inside. To prevent this from occurring, control the reaction and obtain a uniform material.

It is reasonable to use water as a heat medium.

It is also possible to add a colorant such as a dye or an additive such as an ultraviolet absorber to the above monomer (system) for polymerization.

Furthermore, the surface of the lens can be modified by chemically treating the surface of the lens with acid or alkali or by applying low-temperature plasma treatment.

Furthermore, the wearing comfort can be improved by graft polymerizing a hydrophilic monomer onto the surface after low temperature plasma treatment or by graft polymerizing a hydrophilic monomer onto the surface in low temperature plasma.

[Effect]

A (co)polymer of monomer or comonomer containing p-siloxanyl styrene exhibits excellent oxygen permeability due to the effect of siloxanyl groups that are bulky and have low surface energy. The p-phinidine group has superior rigidity and rigidity compared to straight-chain alkyl groups, and
It is considered that the oxygen permeability effect of the siloxanyl group can be utilized to the maximum. Furthermore, since the polymer has a low surface energy, deposition of foreign substances such as proteins is less likely to occur, and it is thought that the proliferation of bacteria and the like can be suppressed11.

[Implementation row]

Hereinafter, the present invention will be described in detail based on the practical rows, but the present invention is not limited to these ranges. Note that the parts in the practical rows represent overlapping parts.

Example 1 p-) 96 parts of limethylsilylstyrene and 4 parts of tetraethylene glycol dimethacrylate were mixed well,
Azobis(2,4-dimethylvaleronitrile (A B
0.2 part of VN) was added and stirred to make it homogeneous.The mixture was poured 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, and heated to ℃ for 4 hours.
3 hours at 2℃, 2 hours at 35℃, 2 hours at 40℃, father℃
Polymerization was carried out by heating for 2 hours at 60°C, 2 hours at 60°C, and 2 hours at 105°C in an atmospheric furnace. A round rod of the obtained copolymer was cut, cut and polished to form a contact lens 'lI:f''F.

In addition, lens evaluation/test K1-1 diameter lO~12T
LN.

Using a disk with a thickness of 0.2 μ, the following items were measured.

Oxygen permeability coefficient (DK direct): Xertez Corp
MODFfL 2110 (Mul
Ti-range knalyzer for Dis
Solved mouth zygttr) t-used i. As a result, the oxygen permeability coefficient is 5.85
TP), cm 7 cm” s a c, m Eg.

Vickers hardness (HV): A scratch Vickers hardness meter manufactured by Taiyo Tester Co., Ltd. was used. As a result, the Vickers hardness was 14.2.

Stain resistance: A test piece was immersed in raw egg saline containing 0.2 g of egg white lysozyme at 37° C. for 7 days, and adhesion aCft was measured from the change in absorbance at 280° C.

As a result, the adhesion IT was less than 0.05 part g7cm''.

Examples 2 to 15 Each monomer was thoroughly mixed according to the composition ratio shown in Table IK. The other operations were the same as those in Example 1 to create a real lens.

The lens evaluation report test results are also listed in Table-1.

Comparison rows-1 to 3 Each monomer was well mixed according to the composition ratio shown in Table-1. Other than that, I made contact lens 2 using the same method as the actual m141-1.

The evaluation and test results of the lenses are also listed in Table-2.

Implementation row-16 The lens base material obtained in Example-1 was heated to 0.0% in a plasma polymerization apparatus. The pressure was reduced to ITorr, and the discharge frequency was 13.56 MHz while argon gas was being supplied at 10-(BTP)/yrLjna. ! Low-temperature plasma treatment was performed at a power of 30 W for I seconds. Subsequently, while continuing glow emission wL, NvP was 101 nJ (BTP)/at 30 to 35°C.
mjn, 7 ru! 7, //S is 1O-(ST
MYA was graft-polymerized on the contact lens surface for (a) seconds while supplying at a rate of P)/mjn.

As a result, DKli is 5A8 x 10 CC (ST
P), Akira Yuki.

At 81jO and axHQ, a small amount of egg white lysozyme was not observed.

Practical row-17 The lens base material obtained in Practical row-14 was subjected to low-temperature plasma treatment under the same conditions as Practical row-16.
Stop and set HE MA at 30-31 to 12-(8TP)
/rrL, and H is applied to the contact lens surface for ω seconds.
EMAfc graft polymerization was carried out.

As a result, DKfii 'rl 14.30CC (EI
TP) m7cm” set.

, Hg, and egg white lysozyme were not observed.

Table 2 M I GHz= CH-o-8<(CHs)sM
2 GHz=CH-o-8iccHs)20
EiCCHs)sM 5 CHs= CH-o-('D
(CHshQ+4si(CHs)sM 6 CH,=
CH-o-(CHz)z8j(O8j(CBs)s)s
AI) Lis(trimethylsiloxy)silylpropyl methacrylate A,2 2,2.2-)lifluoroethyl methacrylate A3 Hexafluoroinglovyl methacrylate A4 Methyl methacrylate A5 2-hydroxyethyl methacrylate A5 N
-Vinyl-2-pyrrolidone A7 Methacrylic acid A8 Ethylene glycol dimethacrylate A9 Diethylene glycol dimethacrylate 10 Triethylene glycol dimethacrylate 11 Tetraethylene glycol dimethacrylate A 12 Styrene [Effects of the invention] As described above, one bottle Monomers or comonomers containing p-siloxanyl styrene at 13 eK (7)
(Co) IE combination t! Due to the steric effect of the s-siloxanyl group and the p-phinidine group and the effect of low surface energy,
It has excellent oxygen permeability and stain resistance. ! Ta,
These effects are even greater, and the contact lenses can be worn continuously for long periods of time, as they can supply sufficient oxygen to the cornea even during sleep, are less likely to get dirty, and are easier to care for.

Claims (1)

[Scope of Claims] A contact lens characterized by being made of a polymer or copolymer of monomers or comonomers containing a compound represented by the general formula [I] as an essential component ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ I] (In the formula, R^1, R^2, R^3, R^4 and R^5
each independently represents a hydrocarbon group or fluorohydrocarbon group having 1 to 9 carbon atoms, l is an integer of 0 to 3, n is an integer of 0 to 7, and p and q are each independently 0 or 1.
, r represents an integer from 1 to 3. However, p+q+r=3).