JPH06313865A - Hydrous soft contact lens - Google Patents

Abstract

PURPOSE:To ensure a large percentage of moisture content, high oxygen permea bility and a long-term continuous use under good feeling by composing a specific (meta)acrylate derivative of a monomer alone or a copolymer obtainable from copolymerization with anther monomer allowing such a process. CONSTITUTION:A (meth)acrylate derivative shown in the formula is a monomer or a polymer (polymer A) obtainable as a result of copolymerization with another monomer allowing such a process. In the formula, R1 stands for a hydrogen atom or a methyl group, and R2 for (CH2)m-, (OCH2CH2)n or the like, where (m) is an integer between 1 and 10, and (n) is an integer between 1 and 15. This polymer A has a triethanol ammonioethyl phosphoric acid group as a phospholipid analogous polar group. The water solubility of the polymer A, therefore, increases, and an anti-fouling property against protein, lipid and the like is provided. Preferably, a mixture of one, two or more types of monofunctional vinyl monomer and cross-linking multifunctional monomer may be used as another monomer capable of being copoplymerzied with the (meth) acrylate derivative A.

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 excellent in water content, oxygen permeability and stain resistance.

[0002]

2. Description of the Related Art Conventionally, non-water-containing hard contact lenses mainly containing monomers such as methyl methacrylate and siloxanyl alkyl methacrylate (Japanese Patent Publication No. 52-
No. 33502) is known, but it has a drawback that it is hard to fit into the eyes and the wearing feeling is poor. On the other hand, in order to improve these drawbacks, hydrous soft contact lenses have been developed, and various soft contact lenses containing 2-hydroxyethyl methacrylate as a main component have been used, but the mechanical strength and processability are Although excellent, it cannot be used continuously because the water content is 40% or less. Recently, there has been a demand for a water-containing soft contact lens that can be continuously worn by further increasing the water content of the lens material. For example, in JP-A-49-134345, a hydrous soft contact lens composed of a polymer obtained by copolymerizing N-vinylpyrrolidone as a main component with methyl methacrylate, 2-hydroxyethyl methacrylate, methacrylic acid and the like. Is proposed. However, the water-containing soft contact lens,
Stain tends to adhere, strength decreases, lens processing by cutting and polishing is difficult, yellowing occurs due to repeated sterilization treatment, which is essential for soft contact lenses, and the mechanical strength of the lens decreases when the water content is increased. Due to various problems such as sterilization, it is usually necessary to perform hygiene control using care products such as sterilization by boiling, sterilizing agents, and cleaning solutions.

[0003]

The object of the present invention is to have a high water content, a high oxygen permeability, an excellent feeling of wearing, prevent the contamination due to the adhesion of proteins and lipids, and enable long-term continuous wearing. Another object is to provide a water-containing soft contact lens.

[0004]

According to the present invention, a (meth) acrylate derivative represented by the following general formula 2 is
There is provided a hydrous soft contact lens comprising a polymer obtained by polymerizing with another monomer which is homopolymerizable or copolymerizable (hereinafter referred to as polymer A).

[0005]

[Chemical 2]

The present invention will be described in more detail below.

The hydrous soft contact lens of the present invention comprises a polymer A obtained by polymerizing the (meth) acrylate derivative represented by the general formula 2 with another monomer which can be homopolymerized or copolymerized. Polymer A of the Invention
Since it has a triethanolammonioethyl phosphate group, which is a polar group similar to phospholipids, it increases the water solubility of the polymer A and imparts antifouling properties to proteins and lipids. In the general formula 2, m is 11 or more and n is
When is 16 or more, the production is difficult.

Examples of the (meth) acrylate derivative include 2- (methacryloyloxy) ethyl-2 '.
-(Triethanolammonio) ethyl phosphate, 2-
(Acryloyloxy) ethyl-2 '-(triethanolammonio) ethylphosphoric acid, 4- (methacryloyloxy) butyl-2'-(triethanolammonio) ethylphosphoric acid, 4- (acryloyloxy) butyl-2 '
-(Triethanolammonio) ethyl phosphate, (2-
Methacryloyloxy-1-methyl) ethyl-2'-
(Triethanolammonio) ethyl phosphoric acid, (2-acryloyloxy-1-methyl) ethyl-2 ′-(triethanolammonio) ethylphosphoric acid, 4- (methacryloyloxy) butyl-2 ′-(triethanolammonio) Ethyl phosphoric acid, 4- (acryloyloxy) butyl-2 '-(triethanolammonio) ethyl phosphoric acid, 6- (methacryloyloxy) hexyl-2'-
(Triethanolammonio) ethyl phosphoric acid, 6- (acryloyloxy) hexyl-2 '-(triethanolammonio) ethylphosphoric acid, 9- (methacryloyloxy) nonyl-2'-(triethanolammonio) ethylphosphoric acid, 9 -(Acryloyloxy) nonyl-2'-
(Triethanolammonio) ethyl phosphoric acid, (5-methacryloyloxy-3-oxa) pentyl-2'-
(Triethanolammonio) ethyl phosphoric acid, (5-acryloyloxy-3-oxa) pentyl-2 '-(triethanolammonio) ethylphosphoric acid, (8-methacryloyloxy-3,6-dioxa) octyl-2'-
(Triethanolammonio) ethyl phosphate, (8-acryloyloxy-3,6-dioxa) octyl-2 ′
Examples thereof include- (triethanolammonio) ethyl phosphoric acid. The higher the number of carbon atoms in the (meth) acrylate derivative, the lower the hydrophilicity of the obtained polymer.

The method for synthesizing the (meth) acrylate derivative used in the present invention is not particularly limited, but for example, hydroxyalkyl (meth)
Acrylate and 2-chloro-2-oxo-1,3,2
By reacting with dioxaphosphorane in the presence of an amine to obtain (2-oxo-1,3,2-dioxaphosphoryloxy) alkyl- (meth) acrylate, and then reacting with triethanolamine How to make
Or hydroxyalkyl (meth) acrylate,
Reacting with 2-bromoethylphosphoryl dichloride,
The (meth) acrylate derivative can be synthesized by a method of obtaining (meth) acryloyloxyalkyl-2-bromoethylphosphoric acid and then reacting it with triethanolamine. Thus obtained (meta)
The acrylate derivative is preferably purified by a known method such as recrystallization.

The other monomer copolymerizable with the (meth) acrylate derivative is not particularly limited as long as it is a copolymerizable monomer, but is preferably a monofunctional vinyl monomer and a crosslinkable polyfunctional monomer. It is possible to use one kind or a mixture of two or more kinds.

Examples of the monofunctional vinyl monomer include styrene, methyl styrene, methyl nucleus-substituted styrene, chloro nucleus-substituted styrene, methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate and (meth) acryl. 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, n-butyl vinyl ether, diethyl. Examples thereof include itaconate and di-n-butyl itaconate. The monofunctional vinyl monomer is used to adjust the water content and mechanical strength of a water-containing soft contact lens.

Further, as the crosslinkable polyfunctional monomer,
Allyl (meth) acrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol (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, methylenebisacrylamide, triallyl trimellitate, triallyl cyanurate, divinyl adipate, 1,4-butanediol dimethacrylate, etc. . The crosslinkable polyfunctional monomer can be used to improve the heat resistance, processability and shape stability of the hydrous soft contact lens, and it is preferable to use at least one crosslinkable polyfunctional monomer.

The polymer A constituting the hydrous soft contact lens of the present invention is produced by polymerizing the (meth) acrylate derivative and a specific polymerization initiator in an atmosphere of a specific inert gas. be able to.

The polymerization initiator is not particularly limited as long as it is an ordinary radical initiator, and for example, benzoyl peroxide, diisopropylperoxydicarbonate, t-butylperoxy-2-ethylhexanoate, t -Butylperoxypivalate, t-butylperoxyisobutyrate, lauroyl peroxide, azobisisobutyronitrile, azobis (2,4-dimethylvaleronitrile), benzoin methyl ether, benzoin ethyl ether and the like can be preferably mentioned. .

As the inert gas, nitrogen, helium, argon and the like can be preferably mentioned.

In the present invention, when the above-mentioned (meth) acrylate derivative is copolymerized with the above-mentioned other copolymerizable monomer to synthesize the polymer A, the charged amount is 100 parts by weight of the (meth) acrylate derivative. With respect to parts, the copolymerizable vinyl monomer is preferably 10,000 to 1 part by weight, and particularly preferably 5000 to 5 parts by weight. When the charged amount exceeds 10000 parts by weight, the water content and heat resistance of the resulting water-containing soft contact lens are remarkably lowered, and the antifouling effect is not sufficient. On the other hand, when the amount is less than 1 part by weight, copolymerization results It is not preferable because the effect is not sufficient. When the crosslinkable polyfunctional monomer is used, the amount charged is preferably 50 parts by weight or less, and particularly preferably 20 parts by weight, based on 100 parts by weight of the (meth) acrylate derivative. When the charged amount exceeds 50 parts by weight, the water content of the obtained water-containing soft contact lens decreases, and the wearing feeling deteriorates, which is not preferable. Further, with respect to 100 parts by weight of the polymer A, the charging amount of the polymerization initiator is preferably 10 parts by weight or less, and particularly preferably 5 parts by weight or less. The reaction temperature varies depending on the type of polymerization initiator, but is 20 to 140 ° C.
Is preferable, and 40 to 110 ° C. is particularly desirable. The polymerization time is preferably 6 to 120 hours, but particularly preferably 40 to 100 hours. Furthermore, a colorant such as a dye, an ultraviolet absorber, or a monomer having such a function may be added to the polymer A.

The hydrous soft contact lens of the present invention is prepared by injecting and sealing the above components in a mold of metal, glass, plastic or the like, polymerizing by heating or light, and then cutting or polishing the polymer A, for example. It can be obtained by a method of hydrating and swelling as a lens. Further, it can be obtained by a method of directly forming a lens by a casting polymerization method, a method of casting while irradiating with light, or the like.

The water content of the hydrous soft contact lens of the present invention is preferably 40 to 90%, particularly 45 to 80%.
Is desirable. When the water content is less than 40%, the oxygen permeability is low and the wearing comfort is not good, and when it exceeds 90%, sufficient strength cannot be obtained, which is not preferable.

[0019]

The hydrous soft contact lens of the present invention has a high water content and a high oxygen permeability, and is excellent in antifouling property, prevention of denaturation of the lens and wearing feeling, so that it can be continuously worn for a long time. It can be used as a lens.

[0020]

EXAMPLES The present invention will be described in more detail with reference to examples below, but the present invention is not limited thereto.

[0021]

Example 1 2- (methacryloyloxy) ethyl-
2 '-(Triethanolammonio) ethyl phosphoric acid 5g
And 4.8 g of 2-hydroxyethyl methacrylate,
0.2 g of ethylene glycol dimethacrylate, t-
A mixed solution containing 0.02 g of butylperoxypivalate was poured into a test tube-shaped glass mold, and the system was repeatedly degassed by nitrogen substitution, and the mold was sealed and then heat-polymerized. The heating was carried out in a thermostatic chamber up to 40 to 120 ° C. over 50 hours, and after the completion of the polymerization, a colorless compound was taken out from the mold. The obtained compound was cut and polished by a usual processing method to prepare a contact lens or a test piece having a predetermined shape, and the water content, oxygen permeability, and stain resistance were measured by the following methods. . The measurement results are shown in Table 1.

Moisture content: After being immersed in 0.9% physiological saline and swollen, the water content was determined by weight change. Moisture content (% by weight) = (W1-W2) / W1-100 W1: Weight with saturated water content W2: Weight with dehydration / drying of lens Oxygen permeability coefficient; Seikaken film oxygen permeation meter (Rika Seiki Co., Ltd. ) Manufactured by the company, product name “K-316”),
It measured at 35 degreeC and 0.9% physiological saline.

Antifouling property: After immersing the contact lens in a physiological saline solution containing 0.39% by weight of albumin, 0.17% by weight of lysozyme and 0.105% by weight of globulin at 35 ° C. for 2 weeks, After washing with physiological saline, proteins were separated from the contact lenses with a surfactant.
A reagent for protein quantification was injected into the separated solution, and the amount of protein adsorbed on the contact lens was measured.

[0024]

Examples 2 to 9 2- (methacryloyloxy) ethyl-2 '-(triethanolammonio) ethyl phosphoric acid, 2-hydroxyethyl methacrylate, and ethylene glycol dimethacrylate have the compositions and composition ratios shown in Table 1. The reaction was carried out according to Example 1 except that the above was changed. Table 1 shows each measurement result of the obtained compound.

[0025]

[Comparative Examples 1 and 2] 2- (methacryloyloxy) ethyl-2 '-(triethanolammonio) ethyl phosphoric acid, 2-hydroxyethyl methacrylate and ethylene glycol dimethacrylate have the compositions and composition ratios shown in Table 1. The reaction was carried out according to Example 1 except that the above was changed. Table 1 shows each measurement result of the obtained compound.

[0026]

[Table 1]

Claims (2)

[Claims] 1. A hydrous soft contact lens comprising a polymer obtained by polymerizing a (meth) acrylate derivative represented by the following general formula 1 with another monomer which is homopolymerizable or copolymerizable. [Chemical 1] 2. A water-containing polymer comprising a polymer obtained by copolymerizing the (meth) acrylate derivative according to claim 1, a copolymerizable monofunctional vinyl monomer, and a crosslinkable polyfunctional monomer. Sex soft contact lens.