JP3227811B2 - Hydrous soft contact lens - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a water-containing soft contact lens, and more particularly, to a water-containing soft contact lens having a high water content and a high oxygen permeability and, at the same time, having excellent antifouling properties.

[0002]

2. Description of the Related Art A water-containing soft contact lens is easier to see and is more comfortable to wear than a non-water-containing hard contact lens containing, for example, methyl methacrylate, siloxanylalkyl methacrylate, or the like as a raw material monomer.

Hitherto, as a water-containing soft contact lens, a contact lens mainly composed of 2-hydroxyethyl methacrylate, which has a water content of 40% or less but is excellent in mechanical strength and workability, has been known. Furthermore, in recent years, a high water content soft contact lens for continuous wearing by increasing the water content of a contact lens material has been developed. For example, a soft contact lens or the like in which N-vinylpyrrolidone is a main component and methyl methacrylate, 2-hydroxyethyl methacrylate, or methacrylic acid is copolymerized is known.

However, the soft contact lens containing N-vinylpyrrolidone as a main component is liable to be stained and deteriorates in strength, and it is difficult to process the lens by cutting and polishing. Various problems such as yellowing due to repetition of the bacterial treatment occur.
On the other hand, in the case of the soft contact lens containing 2-hydroxyethyl methacrylate as a main component, the above problem does not occur. However, since the water content is low, it takes a long time to saturate the water, and there are production problems such as variation in the water content. have.

In general, soft contact lenses have problems in hygiene such as adhesion of proteins and lipids, propagation of bacteria, and problems such as a decrease in mechanical strength of lenses when the water content is increased. It is necessary to control hygiene using care products such as germicides, germicides, and cleaning solutions.

[0006]

SUMMARY OF THE INVENTION It is an object of the present invention to have a high water content and high oxygen permeability, to improve the feeling of wearing and the effect on the eyes, and to suppress the adhesion and deposition of protein and lipid stains. It is an object of the present invention to provide a water-containing soft contact lens which can be worn continuously for a long time.

[0007]

According to the present invention, it is obtained by polymerizing a raw material component containing a fumaric diester represented by the following general formula (hereinafter referred to as fumaric diester 1). A hydrous soft contact lens is provided.

[0008]

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

The water-containing soft contact lens of the present invention is characterized by being obtained by polymerizing a raw material component containing a fumaric acid diester having a specific phospholipid-like polar group.

The hydrous soft contact lens of the present invention is not particularly limited as long as it can be obtained by polymerizing the above-mentioned specific raw material components, but its number average molecular weight is preferably from 1,000 to 100,000. preferable. The water content is preferably 20% or more, particularly preferably 30 to 80%.

In the present invention, the specific fumaric acid diester which is an essential raw material component is the fumaric acid diester 1 represented by the general formula (2). In the fumaric acid diester 1, when the number of carbon atoms of R ₁ and R ₂ exceeds 20, the hydrophobicity increases, and when the number of carbon atoms of R ₄ exceeds 8, the hydrophilicity decreases and the polymerizability decreases. When the value is reduced and n exceeds 8, the mechanical strength of the polymer obtained upon polymerization is reduced.

The fumaric acid diester 1 is, for example, 2- (isopropylfumaroyloxy) ethyl-2 ′
-(Trimethylammonio) ethyl phosphoric acid, 2- (t-
Butyl fumaroyloxy) ethyl-2 '-(trimethylammonio) ethyl phosphate, 2- (cyclohexyl fumaroyloxy) ethyl-2'-(trimethylammonio) ethyl phosphate, 2- (cyclohexyl fumaroyloxy) ethyl-2 '-(Triethylammonio) ethylphosphoric acid, 3- (isopropylfumaroyloxy) propyl-2'-(trimethylammonio) ethylphosphoric acid,
-(Sec-butylfumaroyloxy) butyl-2'-
(Trimethylammonio) ethyl phosphate, 4- (allyl fumaroyloxy) butyl-2 ′-(trimethylammonio) ethyl phosphate, 2- (isopropylfumaroyloxy) ethyl-2 ′-(triethylammonio) ethyl phosphate, 2- (cyclohexyl fumaroyloxy) ethyl-2 '-(tributylammonio) ethyl phosphoric acid, 2
-(T-butylfumaroyloxy) ethyl-2 '-(tri-2 "-hydroxyethylammonio) ethylphosphoric acid, 5- (isopropylfumaroyloxy) ethoxyethyl-2'-(trimethylammonio) ethylphosphoric acid,
Ethyl di-[(2-trimethylammonioethyl) phosphate] fumarate, 2- (phenylfumaroyloxy) ethyl-2 ′-(trimethylammonio) ethylphosphate,
2- (hydroxyethyl fumaroyloxy) ethyl-
2 ′-(trimethylammonio) ethyl phosphoric acid, 5-
(Hydroxyethyl fumaroyloxy) isopropoxyisopropyl-2 ′-(trimethylammonio) ethyl phosphoric acid and the like can be preferably mentioned, and can be used alone or as a mixture at the time of polymerization.

To prepare the fumaric acid diester 1, for example, a fumaric acid diester such as a hydroxyalkyl-alkyl fumaric acid diester and 2-chloro-2-
By reacting with a phosphorane compound such as oxo-1,3,2-dioxaphosphorane or 2-bromoethylphosphoryl dichloride in the presence of an amine at 0 to 60 ° C. for 1 to 20 hours, (2-oxo-1 , 3,2-dioxaphosphoroyloxy) alkyl-alkyl fumaric acid diester or alkyl fumaroyloxyalkyl-2′-bromoethyl phosphoric acid, and the like. At 80 ° C, 1-4
It can be obtained by a method of reacting for 0 hour or the like, and the obtained fumaric acid diester 1 can be purified by a known method such as recrystallization before being subjected to polymerization.

In the present invention, as a raw material component, in addition to the fumaric acid diester 1, a copolymerizable vinyl monomer or the like can be further used, if desired. Examples of the copolymerizable vinyl monomer include styrene, methyl styrene, styrene substituted with methyl nucleus, styrene substituted with chloro nucleus, methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, (meth)
Acrylic acid, (meth) acrylamide, N, N-dimethyl (meth) acrylamide, 2-hydroxyethyl (meth) acrylate, N-vinylpyrrolidone, vinylpyridine, vinyl acetate, vinyl propionate, vinyl pivalate, methyl vinyl ether, ethyl Vinyl ether,
monofunctional vinyl monomers such as n-butyl vinyl ether, diethyl itaconate, di-n-butyl itaconate;
Allyl (meth) acrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth)
Acrylate, tetraethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, 1,4-butanediol di (meth) acrylate, divinylbenzene, diallyl phthalate, diethylene glycol bisallyl carbonate, methylene bisacrylamide, trimellitic acid Examples include crosslinkable polyfunctional monomers such as triallyl, triallyl cyanurate, and divinyl adipate.By using these copolymerizable vinyl monomers, it is possible to obtain water-containing soft contact lenses, The strength can be adjusted appropriately.

When the copolymerizable vinyl monomer is used, the mixing ratio is preferably from 2000 to 1 part by weight, more preferably from 1000 to 1 part by weight, per 100 parts by weight of fumaric acid diester.
A range of from 5 to 5 parts by weight is preferred. In this case, when the amount exceeds 2000 parts by weight, the water content and heat resistance of the obtained water-containing soft contact lens become extremely low, and when the amount is less than 1 part by weight, the effect by copolymerization is not sufficient, which is not preferable.

In order to produce the water-containing soft contact lens of the present invention, a polymerization initiator is added to and mixed with the above-mentioned raw material components, and this is mixed with a desired shape of metal, glass or plastic, for example, a test tube or lens. , And the mixture is sealed, and then heated or polymerized by light to obtain a lens material or a lens-shaped product. Further, the obtained material is cut and polished to form a contact lens, and hydrated and swelled to obtain a desired hydrous soft contact lens. In addition, a method of directly forming a lens by a casting polymerization method, a method of performing casting while irradiating light, and the like can also be performed.

Examples of the polymerization initiator include ordinary radical polymerization initiators such as benzoyl peroxide, diisopropylperoxydicarbonate and t-butylperoxy-2.
-Ethylhexanoate, t-butylperoxypivalate, t-butylperoxydiisobutyrate, lauroyl peroxide, azobisisobutyronitrile, azobis (2,4-dimethylvaleronitrile), benzoin methyl ether, benzoin ethyl ether And the like,
The amount used is 1 to 100 parts by weight of the raw material component.
It is preferably used in an amount of 0 part by weight or less, particularly 5 parts by weight or less.

As the polymerization conditions for producing the above-mentioned hydrous soft contact lens, the polymerization system may be appropriately changed to an inert gas,
For example, it is desirable to replace with nitrogen, helium or the like or to make the atmosphere, and the polymerization temperature and time vary depending on the type of the polymerization initiator, but it is preferably carried out by polymerizing at 20 to 140 ° C. for about 6 to 120 hours. be able to.

In the polymerization, the raw material components
It is also possible to polymerize by adding a coloring agent such as a dye; an additive such as an ultraviolet absorber or other monomer components which do not degrade the function.

[0021]

The water-containing soft contact lens of the present invention has a high water content because it is obtained by polymerizing a fumaric acid diester monomer containing a specific phospholipid-like polar group or copolymerizing it with another monomer. In addition, a sufficient amount of oxygen necessary for physiological activity can be supplied to the cornea, and the feeling of wearing on the eye can be improved. Furthermore, since it is possible to suppress the adhesion and precipitation of proteins, lipids, etc., it is possible to prevent the denaturation of the lens and improve the safety to the eyes, and it has excellent performance that has improved the disadvantages of the conventional hydrous soft contact lens. .

[0022]

The present invention will be described more specifically with reference to examples and comparative examples, but the present invention is not limited to these examples.

[0023]

Example 1 2- (Isopropylfumaroyloxy) ethyl-2 '-(trimethylammonio) ethylphosphate 5
0 g and 50 g of 2-hydroxyethyl acrylate,
A mixed solution containing 0.2 g of t-butyl peroxypivalate as a polymerization initiator was poured into a test tube glass mold, and the system was sufficiently purged with nitrogen and degassed repeatedly. After sealing the mold, the mixture was heated and cured. Heating from 40 ° C to 12 in a constant temperature room
The temperature was raised to 0 ° C over 50 hours. After the polymerization was completed, the cured product was taken out of the mold, and a colorless and transparent polymer was obtained. The obtained polymer was cut and polished by a usual processing method to prepare a contact lens or a test piece having a predetermined shape, and the physical properties shown below were measured. Table 1 shows the raw material components and physical property measurement results.

[0024] by immersing a contact lens in water content 0.9% and sufficiently swollen state was calculated by the following equation. Water content (% by weight) = (W1−W2) / W1 × 100 W1: Weight at the time of saturated water content W2: Weight at the time of dehydration drying of the lens Oxygen transmission coefficient 0.9 at 35 ° C. by a Kaken type film oxygen transmission measuring instrument.
% In normal saline.

Antifouling albumin 0.39 wt%, lysozyme 0.17 wt
%, Globulin 0.105 wt% in physiological saline solution (2 weeks, 35 ° C), then wash with physiological saline, remove protein from contact lens with surfactant, and quantitate protein in the solution Brand name "micro BCA" (manufactured by PIERSC)
Was injected to measure the amount of protein adsorbed on the contact lens.

[0026]

Examples 2 to 5 Curing polymerization was carried out in the same manner as in Example 1 except that the various raw material components shown in Table 1 were used, and processing and physical properties were measured. Table 1 shows the results.

[0027]

Comparative Examples 1 and 2 99 g of 2-hydroxyethyl methacrylate and 1 g of ethylene glycol dimethacrylate
(Comparative Example 1) or processing and physical properties of a contact lens were performed in the same manner as in Example 1 except that 55 g of 2-hydroxyethyl methacrylate, 40 g of N-vinylpyrrolidone and 5 g of ethylene glycol dimethacrylate (Comparative Example 2) were used. evaluated. Table 1 shows the results.

[0028]

[Table 1]

────────────────────────────────────────────────── ─── Continuation of the front page (56) References JP-A-5-107511 (JP, A) JP-A-11-166018 (JP, A) (58) Fields investigated (Int. Cl. ⁷ , DB name) G02C 1/00-13/00

Claims (1)

(57) [Claims] A water-containing soft contact lens obtained by polymerizing a raw material component containing a fumaric acid diester represented by the following general formula 1. Embedded image