JPH04333017A - Hydrous soft contact lens - Google Patents

Abstract

PURPOSE:To provide the contact lens having high oxygen permeability, good gel strength, staining resistance, and transparency by consisting the lens of a copolymer formed by polymerizing its compsn. contg. a specific monomer as an essential component. CONSTITUTION:This contact lens consists of the copolymer formed by polymerizing the compsn. contg. the fluorine monomer, N-vinyl lactam and unstd. carboxylic acid as its essential components. The moisture content of the gel at the time of swelling decreases if the content of the fluorine monomer is too high. The staining resistance tends to degrade if the content is too low. The mechanical strength of the gel at the time of swelling degrades if the content of the N-vinyl lactam is too high. The moisture content decreases if the content thereof is too low. The moisture content of the gel at the time of swelling decreases if the content of the unstd. carboxylic acid is too high. The transparency degrades if the content thereof is too low and, therefore, the compsn. is copolymerized by 1 to 50wt.% fluorine monomer, 0.1 to 20wt.% unstd. carboxylic acid and the balance N-vinyl lactam.

Description

[Detailed description of the invention]

0001

FIELD OF THE INVENTION This invention relates to hydrous soft contact lenses. More specifically, the present invention relates to a water-containing soft contact lens that has excellent water-retaining properties, strength, and transparency.

0002

[Prior Art] Various water-containing soft contact lenses have been known, and materials for such contact lenses include 2-hydroxyethyl methacrylate (
Many of them contain alkylene glycol monomethacrylate as a main component and have a water content of about 30 to 40%, such as 2-HEMA). However, since 2-HEMA is hydrophilic, contact lenses containing it as a main component have some degree of wearability, but do not have sufficient oxygen permeability.
It was difficult to wear it continuously for a long time.

[0003] As an improvement on this, for example, N-
BACKGROUND ART A highly water-containing soft contact lens made of a copolymer obtained by copolymerizing vinylpyrrolidone with methyl methacrylate, 2-HEMA, etc. as a main component has been developed and is already on the market. It is a generally known fact that the higher the water content of the material for soft contact lenses, the higher the oxygen permeability.

[0004] In recent years, many soft contact lenses containing fluorine have been developed for the purpose of further improving stain resistance. For example, JP-A-57-211119 discloses a contact lens material made of poly-2-hydroxyethyl methacrylate containing fluorinated alkyl methacrylate;
The specification discloses a contact lens material made of a copolymer of a fluorine monomer, N-vinylpyrrolidone, and alkyl methacrylate.

[0005]

However, when the fluorine content of such a lens is increased in order to improve its stain resistance, although the lens has excellent stain resistance, its transparency decreases. Particularly when using contact lenses at night, it is important that the lenses have low scattering of light and high transparency in order to reduce so-called glare, in which the surroundings of the light appear dimly lit. Therefore, an object of the present invention is to provide a hydrous soft contact lens that has an appropriate water content and oxygen permeability, and also has stain resistance and high transparency.

[0006]

[Means for Solving the Problems] In order to achieve the above object, the present inventors have made intensive studies and have developed a hydrous soft contact lens made of a copolymer obtained by polymerizing a composition containing a specific monomer as an essential component. It was discovered that the material has high oxygen permeability, good gel strength, stain resistance, and transparency, and the present invention was completed.

That is, the present invention provides a copolymer having a water content of 30%, which is obtained by polymerizing a composition containing a fluorine monomer, an N-vinyl lactam, and an unsaturated carboxylic acid as essential components.
These are the above water-containing soft contact lenses.

The hydrous soft contact lens of the present invention is made of a copolymer obtained by polymerizing a composition containing specific monomers as essential constituents. Among these monomers, examples of fluorine monomers include: Examples include fluorinated alkyl (meth)acrylates, fluorinated hydroxyalkyl (meth)acrylates, fluorinated alkyl itaconates, fluorinated alkyl fumarates, and fluorinated styrenes. Examples of fluorinated alkyl (meth)acrylates include 2,2,2-trifluoroethyl methacrylate, 2,2,2-trifluoroethyl acrylate, 2,2,3,3-tetrafluoropropyl methacrylate, 2, 2,3,3-tetrafluoropropyl acrylate, 2,2,3,3,3-pentafluoropropyl methacrylate, 2,2,3,3.3-pentafluoropropyl acrylate, 2,2,2-trifluoro- 1-trifluoromethylethyl methacrylate, 2,2,2-trifluoro-1-trifluoromethylethyl acrylate, 2,2,3,3-tetrafluoro-t-amyl methacrylate, 2,2,3,3-tetra Fluoro-t-amyl acrylate, 2,2,3,4,
4,4-hexafluorobutyl methacrylate, 2,2
, 3,4,4,4-hexafluorobutyl acrylate, 2,2,3,4,4,4-hexafluoro-t-hexyl methacrylate, 2,2,3,4,4,4-hexafluoro-t -hexyl acrylate, 2,2,3,3
, 4,4,5,5-octafluoropentyl methacrylate, 2,2,3,3,4,4,5,5-octafluoropentyl acrylate, 2,3,4,5,5,5-hexafluoro- 2,4-bis(trifluoromethyl)pentyl methacrylate, 2,3,4,5,5,5-hexafluoro-2,4-bis(trifluoromethyl)pentyl acrylate, 2,2,3,3,4 ,4,5,5,
6,6,7,7-dodecafluoroheptyl methacrylate, 2,2,3,3,4,4,5,5,6,6,7,7
-dodecafluoroheptyl acrylate, 2-hydroxy-4,4,5,5,6,7,7,7-octafluoro-6-trifluoromethylheptyl methacrylate, 2
-Hydroxy-4,4,5,5,6,7,7,7-octafluoro-6-trifluoromethylheptyl acrylate, 2-hydroxy-4,4,5,5,6,6,7,
7,8,9,9,9-dodecafluoro-8-trifluoromethylnonyl methacrylate, 2-hydroxy-4,
4,5,5,6,6,7,7,8,9,9,9-dodecafluoro-8-trifluoromethylnonyl acrylate, 2-hydroxy-4,4,5,5,6,6,7 ,7,
8,8,9,9,10,11,11,11-hexadecafluoro-10-trifluoromethylundecyl methacrylate, 2-hydroxy-4,4,5,5,6,6,
Examples include 7,7,8,8,9,9,10,11,11,11-hexadecafluoro-10-trifluoromethylundecyl acrylate. Examples of fluorinated alkyl itaconates, fluorinated alkyl fumarates, and fluorinated styrenes include bis-2,2,2-trifluoroethyl itaconate, t-
Butyl-(2,2,2-trifluoro-1-trifluoromethyl)ethyl fumarate, isopropyl-(1,1
, 2,2-tetrahydroperfluoro)octyl fumarate, and puntafluorostyrene. Among these, 2,2,2-trifluoroethyl methacrylate, 2,2,2-trifluoroethyl acrylate, 2,2,3,3-tetrafluoropropyl methacrylate, 2,2,3 having 5 to 10 carbon atoms; , 3-tetrafluoropropyl acrylate, 2,2,2-trifluoro-1-trifluoromethylethyl methacrylate, 2,
2,2-trifluoro-1-trifluoromethylethyl acrylate and the like are preferred. Also, these compounds have 1
Seeds may be used, or two or more types may be used in combination.

[0009] Examples of N-vinyl lactams used in the present invention include N-vinyl-2-piperidone and N-vinyl lactam.
Vinyl-2-pyrrolidone, N-vinyl-2-caprolactam, N-vinyl-3-methyl-2-pyrrolidone, N-
Vinyl-3-methyl-2-piperidone, N-vinyl-3
-Methyl-2-caprolactam, N-vinyl-4-methyl-2-pyrrolidone, N-vinyl-4-methyl-2-piperidone, N-vinyl-4-methyl-2-caprolactam, N-vinyl-5-methyl -2-pyrrolidone, N-vinyl-5-methyl-2-piperidone, N-vinyl-3-
Ethyl-2-pyrrolidone, N-vinyl-4,5-dimethyl-2-pyrrolidone, N-vinyl-5,5-dimethyl-
2-pyrrolidone, N-vinyl-3,3,5-trimethyl-2-pyrrolidone, N-vinyl-5-methyl-5-ethyl-2-pyrrolidone, N-vinyl-3,4,5-trimethyl-3- Ethyl-2-pyrrolidone, N-vinyl-6-
Methyl-2-piperidone, N-vinyl-6-ethyl-2
-piperidone, N-vinyl-3,5-dimethyl-2-piperidone, N-vinyl-4,4-dimethyl-2-piperidone, N-vinyl-7-methyl-2-caprolactam,
N-vinyl-7-ethyl-2-caprolactam, N-vinyl-3,5-dimethyl-2-caprolactam, N-vinyl-4,6-dimethyl-2-caprolactam, N-vinyl-3,5,7- Examples include trimethyl-2-caprolactam, and among these, N-vinyl-2-piperidone and N-vinyl-2-pyrrolidone are preferred. Moreover, one type or a mixture of two or more of these can be used.

Examples of the unsaturated carboxylic acid used in the present invention include methacrylic acid, fumaric acid, maleic acid, and itaconic acid. Among these, methacrylic acid and itaconic acid are preferred from the viewpoint of polymerizability, and one or a mixture of two or more of these can be used.

The soft contact lens of the present invention is obtained by copolymerizing a composition containing the above-mentioned monomer as an essential component; however, if too much fluorine monomer is added, the water content of the gel when swollen decreases, and Too much N-vinyl lactam tends to reduce stain resistance, too much N-vinyl lactam reduces the mechanical strength of the gel when swollen, too little reduces water content, and too much unsaturated carboxylic acid reduces the gel's mechanical strength when swollen. The water content of the gel during swelling decreases, and if it is too low, the transparency decreases, so the fluorine monomer is preferably 1 to 50% by weight.
, more preferably 3 to 40% by weight, preferably 0.1 to 20% by weight of unsaturated carboxylic acid, and even more preferably 0.1 to 20% by weight.
2 to 10% by weight, and the balance N-vinyl lactam.

[0012] In addition to these monomers, a difunctional or more functional monomer can be added as a crosslinking agent. For example, ethylene glycol dimethacrylate, ethylene glycol diacrylate, diethylene glycol dimethacrylate, diethylene glycol diacrylate, triethylene glycol dimethacrylate, triethylene glycol diacrylate, tetradecaethylene glycol dimethacrylate, tetradecaethylene glycol diacrylate, allyl methacrylate, allyl Acrylate, trimethylolpropane trimethacrylate, trimethylolpropane triacrylate, 1,3-butanediol dimethacrylate, 1,3-butanediol diacrylate, 1,4-butanediol dimethacrylate, 1,4-butanediol diacrylate, 1,6-hexanediol dimethacrylate, 1,6-hexanediol diacrylate, 1,9-nonanediol dimethacrylate, 1,9-nonanediol diacrylate,
1,10-decanediol dimethacrylate, 1,10
-decanediol diacrylate, neopentyl glycol dimethacrylate, neopentyl glycol diacrylate, 2,2'-bis[p-(γ-methacryloxy-β-hydroxypropoxy)phenyl]propane, methylenebismethacrylamide, methylenebisacrylamide, These include vinyl methacrylate, triallyl cyanurate, dipentaerythritol hexaacrylate, polyethylene glycol #400 dimethacrylate, polypropylene glycol #400 dimethacrylate, and the like. The above crosslinking agent is usually used in an amount of 0.01 to 5.0% by weight of the total composition.

In addition to these essential monomers, other monomers may be added to the extent that the effects of the present invention are not impaired. Examples include hydrophilic monomers such as dimethyl methacrylamide, dimethyl acrylamide, and 2-HEMA, and hydrophobic monomers such as methyl methacrylate, ethyl methacrylate, and styrenes.

When copolymerizing the above composition, when using a polymerization catalyst, for example, benzoyl peroxide, 2,
Catalysts such as 2'-azobisisobutyronitrile, 2,2'-azobismethylisobutyrate, and 2,2'-azobisdimethylvaleronitrile can be used. The addition ratio of the polymerization catalyst is preferably 0.01 to 5% by weight based on the total mixture. Other polymerization methods such as photopolymerization and radiation polymerization may also be used.

Contact lenses may be produced by cutting and polishing the above polymer, or by directly polymerizing a mixture of the monomers in a mold. good. The soft contact lens of the present invention can be obtained by swelling the lens obtained by these methods in physiological saline until it reaches equilibrium. Further, if necessary, a colored lens can be obtained by adding a coloring agent such as a dye or a pigment to the monomer mixture in advance, or by dyeing the lens.

[0016]

EXAMPLES Next, the present invention will be specifically explained with reference to Examples, but the present invention is not limited by these in any way. In the examples, all "parts" represent parts by weight, and each physical property was measured in the following manner. Moisture content: A blow dryer with a temperature of 100°C was used. Oxygen permeability coefficient (DK): A Seikaken film oxygen permeability meter manufactured by Rika Seiki Kogyo Co., Ltd. was used. Haze value: Haze meter (model) manufactured by Tokyo Denshoku Co., Ltd.
TC-HIII) was used. The smaller the number, the higher the transparency. Tensile test: Conducted in water at 25°C.

Examples 1 to 18, Comparative Examples 1 to 6; 10.0 g of each composition shown in Table 1 and 0.2 g of 2,2'-azobisdimethylvaleronitrile as a catalyst were mixed to make polypropylene. The mixture was placed in a test tube, purged with nitrogen, and then sealed. This was immersed in a constant temperature water bath at 40°C for 24 hours. Next, it was immersed in a constant temperature water bath at 50°C for 24 hours, then transferred to a constant temperature bath at 60°C for 5 hours, further left in a constant temperature bath at 80°C for 2 hours, and finally left in a constant temperature bath at 100°C for 1 hour. After cooling, the polymer was taken out from the test tube, cut, and its hardness was measured. Water content, DK, tensile strength, and appearance were measured after the samples were hydrated in water for 24 hours or more. The results are shown in Table 1. Furthermore, when contact lenses were made by cutting these polymers, all of the polymers exhibited good lens shapes when swollen in physiological saline.

[0018]

[Table 1]

[0019]

[Effects of the Invention] According to the present invention, a soft contact lens having high transparency, high water content and high strength can be provided. Such lenses are useful as long-term continuous wear contact lenses with low glare and excellent durability.

Claims (1)

[Claims] 1. A soft contact lens with a water content of 30% or more, which is made of a copolymer obtained by polymerizing a composition containing a fluorine monomer, N-vinyl lactam, and an unsaturated carboxylic acid as essential components.