JP3227810B2 - 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 characterized by being obtained by polymerizing a raw material component containing an itaconic acid diester represented by the following general formula (hereinafter referred to as itaconic acid 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 an itaconic 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 itaconic acid diester, which is an essential raw material component, is the itaconic acid diester 1 represented by the general formula (2). In the itaconic acid diester 1, when R ₁ and R ₂ have more than 20 carbon atoms, the hydrophobicity increases, and when R ₄ exceeds 8 carbon atoms, the hydrophilicity decreases and the polymerizability decreases. If the value is reduced and n exceeds 8, the mechanical strength of the polymer obtained upon polymerization is reduced.

The itaconic acid diester 1 is, for example, 2- (ethylitaconoyloxy) ethyl-2'-
(Trimethylammonio) ethylphosphoric acid, 2- (isopropylitaconoyloxy) ethyl-2 '-(trimethylammonio) ethylphosphoric acid, 3- (sec-butylitaconoyloxy) propyl-2'-(trimethylammonio) ethylphosphoric acid Acid, 4- (ethylitaconoyloxy) butyl-2 ′-(trimethylammonio) ethylphosphoric acid, 4- (n-hexylitaconoyloxy) butyl-2 ′-(trimethylammonio) ethylphosphoric acid, 2-
(Ethylitaconoyloxy) ethyl-2 '-(triethylammonio) ethylphosphate, 3- (isopropylitaconoyloxy) propyl-2'-(tributylammonio) ethylphosphate, 6- (methylitaconoyloxy) hexyl- 2 ′-(trimethylammonio) ethyl phosphoric acid, 2- (myristylitaconoyloxy) ethyl-2 ′-(triphenylammonio) ethyl phosphoric acid,
-(T-butylitaconoyloxy) ethyl-2'-
(Tri-2 "-hydroxyethylammonio) ethyl phosphate, 5- (ethylitaconoyloxy) ethoxyethyl-2 '-(trimethylammonio) ethylphosphate, ethyl di-[(2-trimethylammonioethyl) phosphate ] Itaconate, 2- (allylitaconoyloxy)
Ethyl-2 '-(trimethylammonio) ethylphosphoric acid, 2- (hydroxyethylitaconoyloxy) ethyl-2'-(trimethylammonio) ethylphosphoric acid, 5
-(Hydroxyethylitaconoyloxy) isopropoxyisopropyl-2 '-(trimethylammonio) ethylphosphoric 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 above-mentioned itaconic acid diester 1, for example, itaconic acid diester such as hydroxyalkyl-alkylitaconic acid diester and 2-chloro-
By reacting with a phosphorane compound such as 2-oxo-1,3,2-dioxaphosphorane or 2-bromoethylphosphoryl dichloride in the presence of an amine at 0 to 40 ° C. for 1 to 20 hours, -1,3,2-dioxaphosphoroyloxy) alkyl-alkylitaconic acid diester or alkylitaconoyloxyalkyl-2′-bromoethylphosphoric acid and the like, and then a predetermined tertiary amine such as trimethylamine and pyridine is It can be obtained by a method of reacting at 20 to 80 ° C. for 1 to 40 hours, and the obtained itaconic 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 itaconic 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 2,000 to 1 part by weight, more preferably 100 to 100 parts by weight, per 100 parts by weight of itaconic acid diester.
The range of 0 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 since itaconic acid diester monomer containing a specific phospholipid-like polar group is polymerized or copolymerized with another monomer. In addition, sufficient and sufficient oxygen can be supplied to the cornea for physiological activity, 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- (isopropylitaconoyloxy)
A mixed solution composed of 19 g of ethyl-2 ′-(trimethylammonio) ethyl phosphoric acid, 1 g of allyl methacrylate, and 0.02 g of t-butyl peroxypivalate as a polymerization initiator was injected into a test tube glass mold, and the inside of the system was cooled. The mold was sealed by repeated nitrogen purging and degassing, and then cured by heating. The heating was performed in a constant temperature chamber from 40 ° C. to 120 ° 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 an itaconic acid diester represented by the following general formula 1. Embedded image