JPH0667122A - Soft contact lens - Google Patents

Abstract

PURPOSE:To obtain a soft contact lens high in moisture content and oxygen permeability, excellent in hydrophilicity, small in physiological trouble to cornea, excellent in fitting feeling, capable of fitting for a long time and easy in working at the time of producing lens by containing a specific polymerizable betaine type compound as an essential raw material component. CONSTITUTION:This soft contact lens is obtained by polymerizing the raw material component containing at least one kind of the polymerizable betaine compound expressed by the formula and a copolymer copolymerizable with the polymerizable betaine compound. In the formula, R<1> is hydrogen atom or methyl group, R<2> is methyl group or ethyl group, X is -O- or -NH-, Y is -SO2 or -COO. And (m) is an integer 2-6, (n) is an integer 1-3.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a soft contact lens which has a high water content and is excellent in oxygen permeability and moldability.

[0002]

2. Description of the Related Art A water-containing soft contact lens is compared with a non-water-containing hard contact lens containing methyl methacrylate, siloxanyl alkyl methacrylate or the like as a main monomer (Japanese Patent Publication No. 52-33502).
It is known that it has an advantage of exhibiting an excellent feeling of wearing and being hard to fall off during wearing. Conventionally, as a hydrous soft contact lens, a soft contact lens containing 2-hydroxyethyl methacrylate as a main component and having excellent mechanical strength and processability has been used. However, since the soft contact lens has a low water content of 40% or less, it has a problem that it is not suitable for continuous wear for a long time.

Therefore, a highly hydrous soft contact lens having high oxygen permeability, which is mainly composed of N-vinylpyrrolidone and is copolymerized with methyl methacrylate, 2-hydroxymethacrylate, methacrylic acid or the like, has been developed.

However, in the highly hydrous soft contact lens containing N-vinylpyrrolidone as a main component,
There is a problem that stains such as proteins and lipids are easily attached, and yellowing occurs due to repeated sterilization treatment, and mechanical strength deteriorates. Further, there is a problem that the processability such as cutting and polishing is poor in manufacturing the lens.

On the other hand, a water-containing soft contact lens containing 2-hydroxymethacrylate as a main component has a problem that it takes a long time to be saturated with water because of its poor hydrophilicity and the water content has a remarkable variation. .

[0006]

The object of the present invention is to provide excellent moldability during production, high water content and high oxygen permeability,
An object of the present invention is to provide a soft contact lens which has good hydrophilicity, has less physiological damage to the cornea, has an excellent feeling of wearing, and can be worn continuously for a long period of time.

[0007]

According to the present invention, a polymerizable betaine compound represented by the following general formula (2)
Provided is a soft contact lens, which is obtained by polymerizing a raw material component containing at least one of betaine compound 1) and a comonomer copolymerizable with the polymerizable betaine compound.

[0008]

[Chemical 2]

The present invention will be described in detail below.

The soft contact lens of the present invention is characterized by being obtained by polymerizing a raw material component containing a specific polymerizable betaine type compound and a comonomer copolymerizable with the betaine type compound.

The soft contact lens of the present invention is not particularly limited as long as it is obtained by polymerizing the above specific raw material components, but its number average molecular weight is 1000.
It is preferably 0 or more or one having a three-dimensional network structure by using a crosslinking agent or the like, and the water content is preferably 20% by weight or more.

In the present invention, the specific betaine-type compound which is the essential raw material component is betaine-type compound 1 represented by the general formula 2. The betaine compound 1
In, when m is an integer of 7 or more or n is an integer of 4 or more, the hydrophobicity becomes strong and therefore it cannot be used.

Specific examples of the betaine-type compound 1 preferably include the following chemical formulas 3 to 20.

[0014]

[Chemical 3]

[0015]

[Chemical 4]

[0016]

[Chemical 5]

[0017]

[Chemical 6]

[0018]

[Chemical 7]

[0019]

[Chemical 8]

[0020]

[Chemical 9]

[0021]

[Chemical 10]

[0022]

[Chemical 11]

[0023]

[Chemical 12]

[0024]

[Chemical 13]

[0025]

[Chemical 14]

[0026]

[Chemical 15]

[0027]

[Chemical 16]

[0028]

[Chemical 17]

[0029]

[Chemical 18]

[0030]

[Chemical 19]

[0031]

[Chemical 20]

To produce the betaine compound 1,
For example, N, N-dimethylaminopropyl acrylamide and propanesulfonic acid are reacted with each other in an organic solvent such as toluene, preferably at 40 to 60 ° C. for 1 to 4 hours, to easily produce them in high yield. be able to.

In the present invention, the copolymerizable comonomer which is the essential raw material component is not particularly limited as long as it is a comonomer which is copolymerizable with the betaine compound 1, but particularly, the hydrophilicity of the soft contact lens is not limited. Hydrophilic comonomers are preferred for improvement. Specific examples of the hydrophilic comonomer include 2-hydroxyethyl (meth) acrylate, N-vinylpyrrolidone,
(Meth) acrylic acid, sodium (meth) acrylate,
Acrylonitrile, (meth) acrylamide, N-methyl (meth) acrylamide, N, N-dimethyl (meth)
Acrylamide, N- (meth) acryloylmorpholine, itaconic acid, maleic acid, fumaric acid, sodium itaconate, sodium maleate, sodium fumarate, polyethylene glycol mono (meth) acrylate, vinylbenzenesulfonic acid, sodium vinylbenzenesulfonate or Preferable examples thereof include a mixture of these. Furthermore, in addition to the hydrophilic comonomer, methyl (meth) acrylate, ethyl (meth) acrylate,
(Meth) acrylic acid ester derivatives such as benzyl (meth) acrylate; methyl itaconate, methyl maleate,
Dicarboxylic acid esters such as methyl fumarate; vinyl ester derivatives such as vinyl acetate and vinyl propionate; styrene derivatives such as styrene, chlorostyrene, α-methylstyrene; divinylbenzene, ethylene glycol di (meth) acrylate, diethylene glycol di ( (Meth) acrylate, polyethylene glycol di (meth)
Bifunctional cross-linking agent such as acrylate; tri- or more-functional cross-linking agent such as trimethylolpropane tri (meth) acrylate, tetramethylolmethane tri (meth) acrylate, tetramethylolmethane tetra (meth) acrylate, or a mixture thereof. Can be preferably mentioned. When used, they can be used alone or as a mixture.

In the present invention, the above betaine compound 1
The compounding ratio of 1 to 99% by weight with respect to the entire raw material components,
Particularly, the range of 10 to 80% by weight is preferable. If the mixing ratio of the betaine compound 1 is less than 1% by weight, sufficient hydrophilicity cannot be obtained, and if it exceeds 99% by weight, mechanical strength required for a soft contact lens cannot be obtained, which is not preferable.

To produce the soft contact lens of the present invention, for example, a polymerization initiator is added to the raw material components,
After injecting this into a tube having a desired shape such as metal or glass, the tube is heated or irradiated with light or polymerized by a redox catalyst system under an inert gas atmosphere such as nitrogen or argon or under degassing conditions. By doing so, a lens material can be obtained. At this time, in order to remove the distortion of the lens material, preferably 30 to 150 ° C. after the completion of the polymerization.
It is desirable to carry out an annealing treatment in. Then, the lens material is processed into a lens-shaped product by cutting, polishing, etc., and swollen in water or an organic solvent miscible with water to produce a soft contact lens. A soft contact lens can also be produced by a method of directly obtaining a lens-shaped product by casting polymerization of raw material components in a predetermined mold.

As the above-mentioned polymerization initiator, usual radical polymerization initiators such as benzoyl peroxide, diisopropyl peroxydicarbonate, t-butyl peroxypivalate, azobisisobutyronitrile and azobis (2,2
4-dimethylvaleronitrile) and the like can be preferably mentioned. The amount of the polymerization initiator used is the amount of the raw material component 1
It is preferably 10 parts by weight or less, and particularly preferably 5 parts by weight or less with respect to 00 parts by weight.

The polymerization temperature and time for the above-mentioned polymerization are different depending on the kind and the amount of the polymerization initiator used, but are preferably -70 to 200 ° C, particularly 10 to 120.
At the temperature of 30 ° C., preferably about 30 minutes to 168 hours is desirable.

Further, when carrying out the above-mentioned polymerization, in addition to the above-mentioned essential raw material components, a coloring agent such as a dye or a pigment; an additive such as a UV absorber or an oxidation stabilizer or a polymerizable monomer having these functions is added. May be polymerized.

[0039]

EFFECTS OF THE INVENTION The soft contact lens of the present invention contains a specific polymerizable betaine type compound as an essential raw material component, and therefore has high water content and oxygen permeability, good hydrophilicity, and physiological damage to the cornea. It has less wear and is excellent in wearing feeling, can be worn continuously for a long period of time, and can be easily molded during lens production.

[0040]

The present invention will be described in more detail based on the following examples, but the invention is not intended to be limited thereto.

[0041]

Example 1 As a raw material monomer, 10 g of a compound represented by the following chemical formula 21, diethylene glycol dimethacrylate 1 g, 2-hydroxyethyl methacrylate 9 g and t-butyl peroxypivalate 0.1 g as a polymerization initiator were mixed, and the mixture was made of glass. After being injected into the polymerization tube, the polymerization tube was replaced with nitrogen gas, decompressed, and sealed. The glass tube was heated from 40 ° C. to 120 ° C. over 12 hours to carry out a polymerization reaction to obtain a rod-shaped cured product. The obtained cured product was cut and polished to obtain a disk-shaped sample having a thickness of 0.5 mm.
Then, the water content, oxygen permeability coefficient and processability of the sample were measured and evaluated according to the following methods. The measurement results and evaluation are shown in Table 1.

[0042]

[Chemical 21]

(1) Water Content The weight of the obtained sample was measured and designated as W2. Then, the sample was allowed to stand at 40 ° C. in ion-exchanged water for 1 week to be sufficiently swollen, and then the weight was measured and designated as W1. The water content was calculated based on the following formula. Moisture content (% by weight) = (W1-W2) / W1 × 100 (2) Oxygen permeability coefficient At 35 ° C. by a science research film oxygen permeation measuring device,
It was measured in 0.9% saline. (3) Workability When processing the rod-shaped cured product into a disk-shaped sample having a thickness of 0.5 mm, no cracks or cracks were found during cutting, and ◯ was evaluated if any of the above was bad.

[0044]

Example 2 Samples were obtained and evaluated in the same manner as in Example 1 except that 10 g of the compound represented by the following chemical formula 22, 10 g of ethylene glycol dimethacrylate and 9 g of acrylic acid were used as raw material monomers. . The results are shown in Table 1.

[0045]

[Chemical formula 22]

[0046]

Example 3 A sample was obtained and evaluated in the same manner as in Example 1 except that 10 g of the compound represented by the following chemical formula 23, 1 g of ethylene glycol dimethacrylate and 9 g of acrylic acid were used as raw material monomers. . The results are shown in Table 1.

[0047]

[Chemical formula 23]

[0048]

Example 4 A sample was obtained in the same manner as in Example 1 except that 10 g of the compound represented by the following chemical formula 24, 1 g of ethylene glycol dimethacrylate and 9 g of 2-hydroxyethyl methacrylate were used as raw material monomers, and each evaluation was performed. I went. The results are shown in Table 1.

[0049]

[Chemical formula 24]

[0050]

Example 5 A sample was obtained in the same manner as in Example 1 except that 10 g of the compound represented by the following chemical formula 25, 1 g of ethylene glycol dimethacrylate and 9 g of 2-hydroxyethyl methacrylate were used as raw material monomers, and each evaluation was performed. I went. The results are shown in Table 1.

[0051]

[Chemical 25]

[0052]

Example 6 A sample was obtained in the same manner as in Example 1 except that 10 g of the compound represented by the following chemical formula 26, 1 g of ethylene glycol dimethacrylate and 9 g of 2-hydroxyethyl methacrylate were used as raw material monomers, and each evaluation was performed. I went. The results are shown in Table 1.

[0053]

[Chemical formula 26]

[0054]

Example 7 A sample was prepared in the same manner as in Example 1 except that 10 g of the compound represented by the following chemical formula 27, 1 g of diethylene glycol dimethacrylate, 4 g of N-vinylpyrrolidone and 5 g of 2-hydroxyethyl methacrylate were used as raw material monomers. Was obtained and each evaluation was performed. The results are shown in Table 1.

[0055]

[Chemical 27]

[0056]

Example 8 A sample was prepared in the same manner as in Example 1 except that 10 g of a compound represented by the following chemical formula 28, 1 g of diethylene glycol dimethacrylate, 4 g of N-vinylpyrrolidone and 5 g of 2-hydroxyethyl methacrylate were used as raw material monomers. Was obtained and each evaluation was performed. The results are shown in Table 1.

[0057]

[Chemical 28]

[0058]

Example 9 A sample was prepared in the same manner as in Example 1 except that 10 g of a compound represented by the following chemical formula 29, 1 g of diethylene glycol dimethacrylate, 4 g of N-vinylpyrrolidone and 5 g of 2-hydroxyethyl methacrylate were used as raw material monomers. Was obtained and each evaluation was performed. The results are shown in Table 1.

[0059]

[Chemical 29]

[0060]

Example 10 The following chemical formula 30 was used as a raw material monomer.
A sample was obtained in the same manner as in Example 1 except that 5 g of the compound represented by the formula, 1 g of diethylene glycol dimethacrylate, 5 g of N-vinylpyrrolidone and 9 g of acrylic acid were used, and each evaluation was performed. The results are shown in Table 1.

[0061]

[Chemical 30]

[0062]

Example 11 The following chemical formula 31 was used as a raw material monomer.
A sample was obtained in the same manner as in Example 1 except that 5 g of the compound represented by the formula, 1 g of diethylene glycol dimethacrylate, 5 g of N-vinylpyrrolidone and 9 g of acrylic acid were used, and each evaluation was performed. The results are shown in Table 1.

[0063]

[Chemical 31]

[0064]

Example 12 The following chemical formula 32 was used as a raw material monomer.
A sample was obtained in the same manner as in Example 1 except that 5 g of the compound represented by the formula, 1 g of diethylene glycol dimethacrylate, 5 g of N-vinylpyrrolidone and 9 g of acrylic acid were used, and each evaluation was performed. The results are shown in Table 1.

[0065]

[Chemical 32]

[0066]

Example 13 The following chemical formula 33 was used as a raw material monomer.
Except that 15 g of the compound represented by the formula, 1 g of diethylene glycol dimethacrylate and 4 g of acrylic acid were used,
A sample was obtained in the same manner as in Example 1 and each evaluation was performed.
The results are shown in Table 1.

[0067]

[Chemical 33]

[0068]

Example 14 The following chemical formula 34 was used as a raw material monomer.
Except that 15 g of the compound represented by the formula, 1 g of diethylene glycol dimethacrylate and 4 g of acrylic acid were used,
A sample was obtained in the same manner as in Example 1 and each evaluation was performed.
The results are shown in Table 1.

[0069]

[Chemical 34]

[0070]

Example 15 The following chemical formula 35 was used as a raw material monomer.
Except that 15 g of the compound represented by the formula, 1 g of diethylene glycol dimethacrylate and 4 g of acrylic acid were used,
A sample was obtained in the same manner as in Example 1 and each evaluation was performed.
The results are shown in Table 1.

[0071]

[Chemical 35]

[0072]

Comparative Example 1 Example 1 was repeated except that 0.02 g of ethylene glycol dimethacrylate and 19.98 g of 2-hydroxyethyl methacrylate were used as raw material monomers.
Samples were obtained in the same manner as above and each evaluation was performed. The results are shown in Table 1.

[0073]

Comparative Example 2 A sample was obtained and evaluated in the same manner as in Example 1 except that 1 g of ethylene glycol dimethacrylate, 11 g of 2-hydroxyethyl methacrylate and 8 g of N-vinylpyrrolidone were used as raw material monomers. The results are shown in Table 1.

[0074]

[Table 1]

Claims (1)

[Claims] 1. A polymer obtained by polymerizing a raw material component containing at least one polymerizable betaine compound represented by the following general formula 1 and a comonomer copolymerizable with the polymerizable betaine compound. And soft contact lenses. [Chemical 1]