JP2000191730A - Monomer for ophthalmic lens, polymer for ophthalmic lens and contact lens using the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a monomer for ophthalmic lenses comprising a specific compound having silicon group, hydroxyl group and ether bonds in the molecule, excellent in compatibility with a hydrophilic monomer and providing a highly hydrophilic polymer for the ophthalmic lenses prepared by polymerizing the monomer and having a high oxygen permeability. SOLUTION: This monomer for ophthalmic lenses is represented by formula I [R2 to R4 are each H, a (substituted)alkyl or the like; (k) is 0-20]. A monomer represented by formula II is preferred in the monomer. The polymer for the ophthalmic lenses is preferably obtained by including the monomer as a polymerization component. The polymer can be prepared by copolymerization thereof with other monomers. Acrylic acid, methacrylic acid itaconic acid, or the like, are cited as the comonomer in this case. The polymer is preferably obtained by using a monomer having >=2 copolymerizable carbon-carbon unsaturated bonds in one molecule in >=0.5 wt.% copolymerization ratio as a copolymerization component.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a monomer for an ophthalmic lens and a polymer for an ophthalmic lens. The monomer for an ophthalmic lens and the polymer for an ophthalmic lens are suitably used as an ophthalmic lens such as a contact lens, an intraocular lens, and an artificial cornea.

[0002]

2. Description of the Related Art Conventionally, monomers having a silicon group have been known as monomers for ophthalmic lenses.

[0003] For example, 3- [tris (trimethylsiloxy) silyl] propyl methacrylate is widely used as a monomer for ophthalmic lenses. However, 3- [tris (trimethylsiloxy) silyl] propyl methacrylate is inferior in compatibility with a hydrophilic monomer such as 2-hydroxyethyl methacrylate, and has a drawback that a transparent polymer cannot be obtained when copolymerized with these. Was.

For example, Japanese Patent Publication Nos. 56-39450 and 56-40324 describe monomers represented by the following formulas (b1) and (b2).

[0005]

Embedded image These monomers have excellent compatibility with a hydrophilic monomer such as 2-hydroxyethyl methacrylate, and the polymer obtained by polymerizing the monomer has relatively high oxygen permeability and high hydrophilicity.

However, in recent years, as a polymer for an ophthalmic lens, higher oxygen permeability has been required in order to enable continuous wearing for a longer time, and monomers of the formulas (b1) and (b2) have been required. The oxygen permeability of the polymer for ophthalmic lenses obtained from the above was insufficient.

[0007]

DISCLOSURE OF THE INVENTION The present invention has excellent compatibility with a hydrophilic monomer such as 2-hydroxyethyl methacrylate, and a polymer for an ophthalmic lens obtained by polymerizing the polymer is highly hydrophilic. An object of the present invention is to provide a monomer for an ophthalmic lens having high oxygen permeability.

[0008]

In order to achieve the above object, the present invention has the following arrangement.

"(1) A monomer for an ophthalmic lens represented by the following general formula (a):

[0010]

Embedded image [R ^{2 to} R ⁴ each independently represent H, a substituent selected from an optionally substituted alkyl group and an optionally substituted aryl group.

K represents an integer of 0 to 20. (2) A polymer for an ophthalmic lens comprising the monomer for an ophthalmic lens according to the above (1) as a polymerization component.

(3) A contact lens using the polymer described in (2) above. "

[0013]

Embodiments of the present invention will be described below.

The monomer for an ophthalmic lens of the present invention has the following constitution.

"A monomer for an ophthalmic lens represented by the following general formula (a):

[0016]

Embedded image [R ^{2 to} R ⁴ each independently represent H, a substituent selected from an optionally substituted alkyl group and an optionally substituted aryl group.

K represents an integer of 0 to 20. ]] Hereinafter, each substituent in the formula (a) will be described.

R ^{2 to} R ⁴ each independently represent H, a substituent selected from an optionally substituted alkyl group and an optionally substituted aryl group, and preferred examples thereof include H, methyl Group, ethyl group, propyl group, butyl group,
Pentyl, hexyl, 2-ethylhexyl, octyl, decyl, undecyl, dodecyl, octadecyl, cyclohexyl, benzyl, phenyl, naphthyl and the like. Among them, H, a methyl group, an ethyl group and a phenyl group are preferred, and a methyl group is most preferred.

K represents an integer of 0 to 20, and is preferably 0 or 1 in order to provide high oxygen permeability.
Most preferably, it is 0.

Among the monomers represented by the general formula (a), those preferred in terms of the balance between oxygen permeability, hydrophilicity and elastic modulus are those represented by the following formula (M1) or (M2). The most preferred is a monomer represented by the formula (M1).

[0021]

Embedded image The monomer for an ophthalmic lens of the present invention has a hydrophobic silicon group, a hydrophilic hydroxyl group and an ether bond in its molecule. This silicon group has a function of improving the oxygen permeability of the obtained copolymer.
However, those having a silicon group, especially those having no hydrophilic group in the molecule, have extremely strong water repellency and are difficult to use as polymers for ophthalmic lenses without copolymerization with a hydrophilic monomer. . However, a hydrophobic monomer having no hydrophilic group has poor copolymerizability with the hydrophilic monomer, and when the amount of the hydrophilic monomer is increased, the obtained copolymer becomes opaque. (In order to increase oxygen permeability, the number of silicon groups must be increased correspondingly. However, since doing so increases the water repellency, it is necessary to copolymerize more hydrophilic monomers.) However, the monomer for an ophthalmic lens of the present invention,
Since it has a hydroxyl group and an ether bond that are hydrophilic in the molecular structure, it is compatible with the hydrophilic monomer at an arbitrary ratio and has good copolymerizability, so that the obtained copolymer is colorless and transparent even when containing water. It becomes.

The polymer for an ophthalmic lens of the present invention can be obtained by polymerizing the monomer for an ophthalmic lens represented by the general formula (a) alone or by copolymerizing with another monomer. is there. The copolymerizable monomer when copolymerized with another monomer is not particularly limited as long as copolymerization is possible, and may be a (meth) acryloyl group, a styryl group, an allyl group,
Monomers having vinyl groups and other copolymerizable carbon-carbon unsaturated bonds can be used.

Hereinafter, some examples will be given, but the present invention is not limited thereto. (Meth) acrylic acid, itaconic acid, crotonic acid, cinnamic acid, vinyl benzoic acid, alkyl (meth) acrylates such as methyl (meth) acrylate, ethyl (meth) acrylate, polyalkylene glycol mono (meth) acrylate, polyalkylene Glycol monoalkyl ether (meth) acrylate, polyalkylene glycol bis (meth) acrylate, trimethylolpropane tris (meth) acrylate, pentaerythritol tetrakis (meth) acrylate, siloxane macromer having a carbon-carbon unsaturated bond at both terminals, etc. Alkyl (meth) acrylates such as functional (meth) acrylates, trifluoroethyl (meth) acrylate and hexafluoroisopropyl (meth) acrylate, 2-hydroxy Chill (meth) acrylate, 2,3-dihydroxypropyl (meth) hydroxyalkyl having a hydroxyl group such as acrylate (meth) acrylates, N, N-dimethylacrylamide, N, N-diethyl acrylamide, N,
N-di-n-propylacrylamide, N, N-diisopropylacrylamide, N, N-din-butylacrylamide, N-acryloylmorpholine, N-acryloylpiperidine, N-acryloylpyrrolidine, N-
(Meth) acrylamides such as methyl (meth) acrylamide, aromatic vinyl monomers such as styrene, α-methylstyrene and vinylpyridine, maleimides, N-
Heterocyclic vinyl monomers such as vinylpyrrolidone;
[Tris (trimethylsiloxy) silyl] propyl (meth) acrylate, 3- [bis (trimethylsiloxy)
Methylsilyl] propyl (meth) acrylate, 3-
[(Trimethylsiloxy) dimethylsilyl] propyl (meth) acrylate, 3- [tris (trimethylsiloxy) silyl] propyl (meth) acrylamide, 3-
[Bis (trimethylsiloxy) methylsilyl] propyl (meth) acrylamide, 3-[(trimethylsiloxy) dimethylsilyl] propyl (meth) acrylamide, [tris (trimethylsiloxy) silyl] methyl (meth) acrylate, [bis (trimethylsiloxy)
[Methylsilyl] methyl (meth) acrylate, [(trimethylsiloxy) dimethylsilyl] methyl (meth) acrylate, [tris (trimethylsiloxy) silyl] methyl (meth) acrylamide, [bis (trimethylsiloxy) methylsilyl] methyl (meth) acrylamide,
[(Trimethylsiloxy) dimethylsilyl] methyl (meth) acrylamide, [tris (trimethylsiloxy)
[Silyl] styrene, [bis (trimethylsiloxy) methylsilyl] styrene, [(trimethylsiloxy) dimethylsilyl] styrene, and the following formulas (c1) to (c1)
And 7) the compound.

[0024]

Embedded image

Embedded image

Embedded image

Embedded image [In the formulas (c1) to (c17), R ¹¹ represents H or a methyl group. R ¹² represents a substituent selected from H, an optionally substituted alkyl group and an optionally substituted aryl group. R ¹³ and R ¹⁴ each independently represent a substituent selected from H, an optionally substituted alkyl group and an optionally substituted aryl group, and R ¹³ and R ¹⁴ are bonded to each other to contain N It may form a ring. Hereinafter, specific examples of each substituent in formulas (c1) to (c17) will be described.

R ¹¹ represents H or a methyl group.

R ¹² represents a substituent selected from H, an alkyl group which may be substituted and an aryl group which may be substituted. Preferred examples thereof include a methyl group, an ethyl group and a propyl group. , Isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, 2-ethylhexyl, octyl, decyl, undecyl, dodecyl, octadecyl, cyclopentyl, cyclohexyl Group, benzyl group, hydroxymethyl group, 2-hydroxyethyl group,
2-hydroxypropyl group, 3-hydroxypropyl group, 2,3-dihydroxypropyl group, 2-hydroxybutyl group, 4-hydroxybutyl group, 2-hydroxypentyl group, 5-hydroxypentyl group, 2-hydroxyhexyl group, 6-hydroxyhexyl group, 3-methoxy-2-hydroxypropyl group, 3-ethoxy-2-hydroxypropyl group, phenyl group, 4-hydroxyphenyl group, 2-hydroxyphenyl group, 4-methoxyphenyl group, 2-methoxy A phenyl group and the following formulas (d1) to
And a substituent represented by (d10).

[0027]

Embedded image [In the formulas (d1) to (d10), m represents an integer of 2 to 20. R ¹³ and R ¹⁴ each independently represent H, a substituent selected from an optionally substituted alkyl group and an optionally substituted aryl group, and R ¹³ and R ¹⁴ are bonded to each other to form N A preferred example of the substituent may be the same as the above-mentioned preferred example of R ¹² . When R ¹³ and R ¹⁴ are bonded to each other to form a ring containing N, specific examples of the portion represented by the following structure (e) include:

Embedded image The following formulas (e1) to (e7) can be exemplified.

[0028]

Embedded image In the polymer for ophthalmic lenses of the present invention, two or more copolymerizable carbon-carbon unsaturated molecules in one molecule means that good mechanical properties can be obtained and good resistance to disinfectants and cleaning solutions can be obtained. It is preferable to use a monomer having a bond as a copolymerization component. The copolymerization ratio of the monomer having two or more copolymerizable carbon-carbon unsaturated bonds in one molecule is preferably 0.1% by weight or more, more preferably 0.3% by weight or more, and more preferably 0.5% by weight or more. Is more preferred.

The (co) polymerization ratio of the monomer for an ophthalmic lens represented by the general formula (a) in the polymer for an ophthalmic lens of the present invention is such that high oxygen permeability and high hydrophilicity are compatible. Is 30% by weight to 100% by weight, more preferably 50% by weight to 99% by weight, and most preferably 60% by weight when other silicon group-containing monomer is not copolymerized.
When copolymerizing another silicon group-containing monomer, the total of the ophthalmic lens monomer represented by the general formula (a) and the other silicon group-containing monomer is 30% by weight or more.
100% by weight, more preferably 50% to 99% by weight, most preferably 60% to 95% by weight.

The polymer for an ophthalmic lens of the present invention may contain an ultraviolet absorbent, a dye, a coloring agent, and the like. Further, an ultraviolet absorber, a dye, and a colorant having a polymerizable group may be contained in a copolymerized form.

When the polymer for an ophthalmic lens of the present invention is obtained by (co) polymerization, a thermal polymerization initiator represented by a peroxide or an azo compound or a photopolymerization initiator is added to facilitate polymerization. Is preferred. In the case of performing the thermal polymerization, a material having an optimum decomposition characteristic for a desired reaction temperature is selected and used. Generally, the 10-hour half-life temperature is 40
Azo initiators and peroxide initiators at -120 ° C are preferred. Examples of the photopolymerization initiator include a carbonyl compound, a peroxide, an azo compound, a sulfur compound, a halogen compound, and a metal salt. These polymerization initiators are used alone or as a mixture, and are used in an amount up to about 1% by weight.

When the polymer for an ophthalmic lens of the present invention is obtained by (co) polymerization, a polymerization solvent can be used.
Various organic and inorganic solvents can be used as the solvent, and there is no particular limitation. Examples include water, methyl alcohol, ethyl alcohol, normal propyl alcohol,
Isopropyl alcohol, normal butyl alcohol,
Alcohol solvents such as isobutyl alcohol and tert-butyl alcohol, methyl cellosolve, ethyl cellosolve, isopropyl cellosolve, butyl cellosolve, propylene glycol monomethyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, glycol ether solvents such as triethylene glycol dimethyl ether, ethyl acetate, Ester solvents such as butyl acetate, amyl acetate, ethyl lactate and methyl benzoate; aliphatic hydrocarbon solvents such as normal hexane, normal heptane and normal octane; alicyclic hydrocarbons such as cyclohexane and ethylcyclohexane. Solvents, ketone solvents such as acetone, methyl ethyl ketone and methyl isobutyl ketone, aromatic hydrocarbons such as benzene, toluene and xylene System solvent, are those of petroleum solvents such as various, it can be used alone or in combination.

As the polymerization method and the molding method of the polymer for an ophthalmic lens of the present invention, known methods can be used. For example, there are a method of once polymerizing and shaping into a round bar or a plate shape, and processing this into a desired shape by cutting or the like, a mold polymerization method, a spin cast polymerization method, and the like.

As an example, the case where the monomer composition containing the monomer for an ophthalmic lens of the present invention is polymerized by a mold polymerization method to obtain an ophthalmic lens will be described below.

The monomer composition is filled into the space between two molds having a predetermined shape. Then, photopolymerization or thermal polymerization is performed to shape the mold. The mold is
It is made of resin, glass, ceramics, metal or the like. In the case of photopolymerization, an optically transparent material is used, and usually, resin or glass is used. In the case of producing a polymer for an ophthalmic lens, in many cases, a void is formed by two opposing molds, and the void is filled with the monomer composition, but depending on the shape of the mold and the properties of the monomer. May be used in combination with a gasket having a purpose of giving a certain thickness to the ophthalmic lens and preventing leakage of the filled monomer composition. The mold filled with the monomer composition in the voids is subsequently irradiated with an actinic ray such as ultraviolet light, or heated in an oven or a liquid tank to be polymerized. There may be a method in which heat polymerization is performed after the photopolymerization, or conversely, a method in which both photopolymerization is performed after the heat polymerization is used. In the case of photopolymerization, it is general to irradiate light containing a large amount of ultraviolet light from a mercury lamp or insect lamp for a short time (usually 1 hour or less). When performing thermal polymerization, the temperature is gradually raised from around room temperature, and the temperature is raised to 60 ° C to 20 ° C over several hours to several tens of hours.
The condition of increasing the temperature to 0 ° C. is preferred in order to maintain the optical uniformity and quality of the ophthalmic lens and to enhance the reproducibility.

The polymer for an ophthalmic lens according to the present invention has a water wettability based on a dynamic contact angle with pure water (at the time of advance, at an immersion speed of 0.1
mm / sec) is preferably 130 ° or less, more preferably 120 ° or less, and most preferably 100 ° or less. The water content is preferably 3% to 50%. The oxygen permeability is determined by an oxygen permeability coefficient [ml (STP) cm · cm ⁻² · sec ⁻¹ · mmH
g ^-1 ] is preferably 60 × 10 ^-11 or more, more preferably 70 × 10 ^-11 or more, and most preferably 95 × 10 ^-11 or more. The tensile modulus is preferably 0.01 to 30 MPa,
0.1-10 MPa is more preferable.

The polymer for an ophthalmic lens of the present invention is particularly suitable as an ophthalmic lens such as a contact lens, an intraocular lens and an artificial cornea.

[0038]

EXAMPLES The present invention will now be described specifically with reference to examples, but the present invention is not limited thereto.

[Measurement Methods] Various measurements in this example were performed by the following methods.

(1) Proton nuclear magnetic resonance spectrum Measured using EX270 type manufactured by JEOL Ltd. Chloroform-d was used as a solvent. The chloroform peak was used as a reference (7.26 ppm).

(2) Dynamic Contact Angle A film-like sample having a size of about 5 mm × 10 mm × 0.2 mm was used as a sample,
The dynamic contact angle at the time of advance with respect to pure water was measured using Model T-6000. The immersion speed was 0.1 mm / sec, and the immersion depth was 7 mm.

(3) Oxygen Permeability Coefficient The oxygen permeability coefficient of a film sample was measured in water at 35 ° C. using a Kakenhi type film oxygen permeability system manufactured by Rika Seiki Kogyo.

(4) Tensile modulus As a sample, 19.5 mm × 15 mm × 0.2 mm
It was measured using a film-shaped material of about the size and using Tensilon RTM-100 manufactured by Orientec. The tensile speed was 100 mm / min, and the distance between grips was 5 mm.

(5) Moisture Content A film having a size of about 10 mm × 10 mm × 0.2 mm was used as a sample. The sample was dried in a vacuum dryer at 40 ° C. for 16 hours, and the weight of the sample (W
d) was measured. Then, the sample was immersed in pure water and kept in a constant temperature bath at 40 ° C. for one night or more to contain water. Then, the surface water was wiped off with a Kimwipe and the weight (Ww) was measured. The water content was determined by the following equation.

Water content (%) = 100 × (Ww−Wd) / Ww Example 1 Synthesis of Monomer for Ophthalmic Lens-1 (1) 50 equipped with a cooling pipe, a stirrer, and a dropping funnel
In a 0 ml three-necked flask, toluene (100 ml), allyl glycidyl ether (120.0 g), chloroplatinic acid hexahydrate (5 mg) and 2,6-di-tert-butyl-4-methylphenol (50 mg) were put. Was. To this, tris (trimethylsiloxy) silane (59.34 g) was added dropwise over 40 minutes while stirring at 70 ° C. After completion of the dropwise addition, the reaction was carried out at 100 ° C. for 50 hours with stirring. After completion of the reaction, the solvent was removed using a rotary vacuum evaporator, followed by distillation under reduced pressure to obtain a colorless transparent liquid (51.6 g). As a result of measuring and analyzing the proton nuclear magnetic resonance spectrum of this liquid, 0.1
around ppm (27H), around 0.4 ppm (2H),
1.6 ppm (2H), 2.6 ppm (1
H) around 2.8 ppm (1H), around 3.2 ppm (1H), around 3.4 ppm (3H), and 3.7 pp.
Since a peak was detected near m (1H), the following equation (J) was obtained.

Embedded image It was confirmed that the compound was represented by the following formula:

(2) A compound (15.0 g) of the formula (J), hydroquinone (0.03 g) and potassium hydroxide (0.24 g) were placed in a 200 ml three-necked flask equipped with a condenser, a stirrer and a dropping funnel. Methacrylic acid (6.29 while stirring at room temperature under a nitrogen atmosphere).
g) was added dropwise over about 30 minutes. After completion of the dropwise addition, the reaction was carried out at 100 ° C. for 8 hours while stirring. After leaving overnight,
Hexane (50 ml) was added and the mixture was stirred at room temperature for 2 hours.
The precipitate was removed by filtration, and the hexane solution was washed several times with 0.5 M sodium hydroxide, and further washed three times with a saturated saline solution. After dehydration by adding anhydrous magnesium sulfate, magnesium sulfate was removed by filtration, and the solvent was distilled off by a rotary vacuum evaporator. Further under reduced pressure 6
Volatile components were removed at 0 ° C. for 4 hours to obtain a colorless transparent liquid (15.0 g). As a result of measuring and analyzing the proton nuclear magnetic resonance spectrum, a value around 0.1 ppm (27H),
Around 0.4 ppm (2H), around 1.6 ppm (2H)
H) 1.9 ppm (3H), 2.6 ppm (1H), 3.3-4.3 ppm (7H), 5.6
Since peaks were detected at around 1 ppm (1H) and around 6.1 ppm (1H), it was confirmed that the mixture was a mixture containing the monomer for an ophthalmic lens represented by the formula (M1) as a main component.

[0047]

Embedded image Example 2 Synthesis of Ophthalmic Lens Monomer-2 200 ml equipped with a cooling tube, a stirrer, and a dropping funnel
In a three-necked flask, 2-hydroxyethyl methacrylate (13.0 g), hydroquinone (0.02 g) and triethylamine (0.35 g) were placed, and the mixture was stirred in a nitrogen atmosphere at room temperature in Example 1- (1). The obtained compound of the formula (J) (20.5 g) was added dropwise over about 30 minutes. After completion of the dropwise addition, the reaction was carried out at 85 ° C. for 8 hours while stirring. After standing overnight, it was dissolved in hexane (300 ml). The precipitate was removed by filtration, and the hexane solution was
After washing several times with M sodium hydroxide, it was further washed three times with a saturated saline solution. After dehydration by adding anhydrous magnesium sulfate, magnesium sulfate was removed by filtration, and the solvent was distilled off by a rotary vacuum evaporator. Further, volatile components were removed under reduced pressure at 60 ° C. for 4 hours to obtain a transparent liquid. As a result of measuring and analyzing the proton nuclear magnetic resonance spectrum, it was found that the concentration was around 0.1 ppm (27H), 0.4 pp.
m (2H), 1.6 ppm (2H), 1.9p
pm (3H), 2.6 ppm (1H), 3.3
~ 4.3 ppm (11H), 5.6 ppm (1
H) and peaks were detected around 6.1 ppm (1H), and it was confirmed that the mixture was mainly composed of the monomer for ophthalmic lenses represented by the formula (M2).

[0048]

Embedded image Example 3 A mixture (60 parts by weight) containing the monomer for an ophthalmic lens of the formula (M1) obtained in Example 1 as a main component (40 parts by weight), 2-hydroxyethyl methacrylate (40 parts by weight) and triethylene glycol dimethacrylate ( 1 part by weight) and Darocur 1173 (CIB) as a polymerization initiator.
(Company A, 0.5 parts by weight), the monomer mixture was degassed under an argon atmosphere, and injected into a contact lens mold made of transparent resin (TPX). The sample was polymerized by light irradiation (6 J / cm ² ) using an insect lamp to obtain a polymer sample for an ophthalmic lens. The sample was clear and free of turbidity.

Example 4 An eye of the formula (M2) obtained in Example 2 instead of the mixture (60 parts by weight) containing the monomer for an ophthalmic lens of the formula (M1) obtained in Example 1 as a main component. A sample of a polymer for an ophthalmic lens was obtained in the same manner as in Example 3 except that a mixture (60 parts by weight) containing a monomer for an ophthalmic lens as a main component was used. The sample was clear and free of turbidity.

Comparative Example 1 3- [tris (trimethylsiloxy) silyl] propyl methacrylate was used in place of the mixture (60 parts by weight) containing the monomer for the ophthalmic lens of the formula (M1) obtained in Example 1 as a main component. Example 3 except that
A polymer sample was obtained in the same manner as described above. The sample was cloudy and was unsuitable as an ophthalmic lens.

Example 5 A mixture (85 parts by weight) containing the monomer for an ophthalmic lens of the formula (M1) obtained in Example 1 as a main component (85 parts by weight), N, N-dimethylacrylamide (14 parts by weight), acrylic acid (1 part by weight), triethylene glycol dimethacrylate (1 part by weight) and diethylene glycol dimethyl ether (25 parts by weight) as a solvent were uniformly mixed, and azobisisobutyronitrile (0.3 part by weight) was used as a polymerization initiator. After the addition, the monomer mixture was degassed under an argon atmosphere and poured between glass plates,
Sealed. First, polymerization was carried out at 100 ° C. for 4 hours.
After cooling down from 0 ° C to 40 ° C over 3.5 hours, 4
It was kept at 0 ° C. for 2 hours or more to obtain a film sample of the polymer for ophthalmic lenses.

The sample was transparent and free of turbidity. After this sample film was immersed in water at room temperature for 24 hours, various physical properties were measured. The results are shown in Table 1. The polymer for ophthalmic lenses showed high oxygen permeability and high hydrophilicity.

Comparative Example 2 Instead of the mixture (85 parts by weight) containing the monomer for the ophthalmic lens of the formula (M1) obtained in Example 1 as a main component, a compound of the following formula (b1) was used as a main component. A film sample of an ophthalmic lens polymer was obtained in the same manner as in Example 5, except that the mixture (85 parts by weight) was used.

[0054]

Embedded image The sample was clear and free of turbidity. After immersing the sample film in water at room temperature all day and night, various physical properties were measured. The results are shown in Table 1. The polymer for ophthalmic lenses showed high hydrophilicity, but low oxygen permeability.

[0055]

[Table 1] Example 6 An ophthalmic lens of formula (M2) obtained in Example 2 was used instead of the mixture (85 parts by weight) containing the monomer for ophthalmic lens of formula (M1) obtained in Example 1 as a main component. A film sample of an ophthalmic lens polymer was obtained in the same manner as in Example 5 except that a mixture (85 parts by weight) containing a monomer for an eye as a main component was used.

The sample was transparent and free of turbidity. After immersing the sample film in water at room temperature all day and night, various physical properties were measured. The results are shown in Table 2. The polymer for ophthalmic lenses showed high oxygen permeability and high hydrophilicity.

Comparative Example 3 Instead of the mixture (85 parts by weight) containing the monomer for the ophthalmic lens of the formula (M1) obtained in Example 1 as a main component, a compound of the following formula (b2) was used as a main component. A film sample of an ophthalmic lens polymer was obtained in the same manner as in Example 5, except that the mixture (85 parts by weight) was used.

[0058]

Embedded image The sample was clear and free of turbidity. After immersing the sample film in water at room temperature all day and night, various physical properties were measured. The results are shown in Table 2. The polymer for ophthalmic lenses showed high hydrophilicity, but low oxygen permeability.

[0059]

[Table 2]

[0060]

Industrial Applicability According to the present invention, a polymer for an ophthalmic lens which is excellent in compatibility with a hydrophilic monomer such as 2-hydroxyethyl methacrylate and obtained by polymerizing the same has high hydrophilicity and high oxygen permeability. Can be provided.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat ゛ (Reference) G02C 7/04 G02C 7/04 F term (Reference) 2H006 BB05 BB07 4C081 AB22 AB23 CA271 CC01 4H049 VN01 VP04 VQ02 VQ07 VQ78 VR21 VR23 VR41 VR43 VU20 4J027 AC03 AC06 AC09 BA08 BA20 CC05 CD04 4J100 AB02Q AB03Q AB07Q AG08Q AJ02Q AJ08Q AL03Q AL08P AL08Q AL19Q AL63Q AL66Q AM19Q AM21Q AN13Q AQ12Q BA02P BA03P BA03QBAQQAQBA08 BA08QBAQQ

Claims (4)

[Claims] 1. A monomer for an ophthalmic lens represented by the following general formula (a). Embedded image [R ^{2 to} R ⁴ each independently represent H, a substituent selected from an optionally substituted alkyl group and an optionally substituted aryl group. k represents an integer of 0 to 20. ] 2. The monomer for an ophthalmic lens according to claim 1, wherein in the general formula (a), R ^{2 to} R ⁴ each represent a methyl group, and k represents 0 or 1. 3. A polymer for an ophthalmic lens comprising the monomer for an ophthalmic lens according to claim 1 as a polymerization component. 4. A contact lens using the polymer according to claim 3.