JPH04370106A - Contact lens having glare-proof performance - Google Patents

Abstract

PURPOSE:To obtain the title contact lens useful for outdoor sports, having physical properties of lens set in a wide range depending upon uses and excellent transparency, comprising a polymer prepared by polymerizing a mixture of a polymerizable monomer and triacetylacetonatoneodymium. CONSTITUTION:The objective contact lens comprising a polymer prepared by polymerizing a mixture which consists of one or more polymerizable monomers such as (meth)acrylic ester and preferably 0.1-20wt.% triacetylacetonatoneodymium shown by the formula, purple crystal, as essential components.

Description

[Detailed description of the invention]

0001

[Industrial Application Field] The present invention relates to a contact lens with anti-glare properties, which selectively absorbs light rays that the human eye perceives as dazzling, and which is ideal for outdoor sports, etc. It is.

0002

2. Description of the Related Art Eyeglasses have been used to correct vision for many years, but in recent years the number of people wearing contact lenses, especially women and athletes, has increased rapidly. Contact lenses have significant optical performance, such as a wide field of view and little aberration, and are not bulky because they do not need to be supported by a frame, so they are widely used, especially by athletes who engage in strenuous exercise. . Under these circumstances, there is a growing demand for contact lenses that can prevent glare in the same way as sunglasses.

[0003]For the human eye, 570nm to 590n
Yellow light around m is said to be perceived as dazzling. If you experience glare at the beach or ski resort in the summer, you generally use tinted lenses such as sunglasses to prevent glare.
In the case of contact lenses, highly colored lenses are also used. However, in this case, all wavelengths of light are uniformly cut, resulting in an insufficient amount of light for wavelengths other than yellow light. Neodymium compounds are 570-590 nm
Because there is sharp absorption in the vicinity, it is possible to selectively reduce the amount of light at wavelengths that are the most dazzling to the human eye, while allowing light in other wavelength ranges to pass through unchanged. Taking advantage of this property, neodymium compounds are mixed into glass to impart anti-glare properties to eyeglass lenses, automobile mirrors, and the like.

[0004] Conventionally, studies have been made on methods of obtaining highly transparent optical plastics with anti-glare properties by introducing neodymium compounds into transparent plastics. As an example, (1) JP-A-58-225148 discloses that a neodymium compound having an average particle size of 0.2 μm to 20 μm, such as neodymium oxide, neodymium carbonate, A photoselective absorptive resin composition in which neodymium hydroxide, neodymium phosphate, neodymium nitrate, neodymium chloride, and neodymium acetate are dispersed (2
) JP-A-1-161024 discloses that a neodymium compound is dissolved in 2-hydroxyethyl methacrylate, a monomer or a polymer is mixed with this solution, and this mixture is polymerized by heating and molded. (3) JP-A-2-153301 discloses a method for producing an anti-glare plate or film, which includes at least one neodymium compound selected from neodymium acrylate and neodymium methacrylate;
Disclosed is a plastic optical element comprising a polymer obtained by polymerizing a monomer mixture containing at least one unsaturated carboxylic acid selected from acrylic acid and methacrylic acid and styrene or a styrene derivative. ing.

[0005]

[Problems to be Solved by the Invention] However, general neodymium compounds are poorly compatible with typical polymerizable monomers that form transparent plastics such as diethylene glycol bisallyl carbonate, methyl methacrylate, and styrene. . Therefore, even if a mixture of these polymerizable monomers and a neodymium compound was directly polymerized by the method (1) above, cloudiness or cloudiness occurred in the polymer, making it unsuitable for use as an optical plastic. Also,
Method (2) above uses neodymium compounds that are said to have poor compatibility with polymerizable monomers, such as neodymium nitrate, which is
It was discovered that it dissolves well in hydroxyethyl methacrylate, and this method is used to manufacture anti-glare plates or films. However, this method always has 2
-Hydroxyethyl methacrylate must coexist, and this 2-hydroxyethyl methacrylate has the disadvantage that it may have an adverse effect on the physical properties of the desired polymer. In addition, in the method (3) above, acrylic acid or methacrylic acid, which is a component that dissolves neodymium compounds such as neodymium acrylate and neodymium methacrylate, and styrene or styrene derivatives are essential components, and these components are essential components. It has the disadvantage that it may adversely affect the physical properties of the polymer. Moreover, the plastic optical element having anti-glare performance obtained by this method cannot be said to be suitable as a material for contact lenses.

The present invention is intended to overcome the above-mentioned drawbacks of the prior art, and its purpose is to use neodymium trisacetylacetonate, which has relatively excellent compatibility with various polymerizable monomers. An object of the present invention is to provide a contact lens having good transparency and an excellent anti-glare effect, which is made of a polymer obtained by polymerizing a mixture of these and a polymerizable monomer suitable as a contact lens material as essential components.

[0007]

[Means for Solving the Problems] That is, the contact lens having anti-glare performance of the present invention has one or more polymerizable monomers and neodymium trisacetylacetonate as essential components, and a mixture thereof is polymerized. It is characterized by being made of a polymer obtained by Furthermore, the polymerizable monomer is a (meth)acrylic ester (hereinafter, acrylic acid and methacrylic acid are collectively abbreviated as (meth)acrylic acid, and acrylate and methacrylate are collectively abbreviated as (meth)acrylate). This is a characteristic feature. Furthermore, it is characterized in that trisacetylacetonatoneodymium is contained in an amount of 0.1 to 20% by weight.

In order to solve the problem, the present inventors conducted extensive research and found that trisacetylacetonate neodymium, which is an acetylacetone complex salt of neodymium, is one of the many polymerizable monomers that form transparent plastics suitable as contact lens materials. The present invention was completed based on the discovery that it dissolves in

The present invention will be explained in detail below. Trisacetylacetonatoneodymium of the present invention is an essential component for imparting antiglare properties, and is preferably contained in an amount of 0.1 to 20% by weight. If it is less than 0.1% by weight, the anti-glare effect will be small, and if it exceeds 20% by weight, the compatibility with the polymerizable monomer will decrease, resulting in cloudiness or cloudiness in the contact lens obtained by polymerization. , which is not preferable because transparency is lost.

The trisacetylacetonate neodymium of the present invention is a neodymium acetylacetone complex salt represented by the following formula and is a purple crystal.

[0011]

[Chemical formula 1]

The polymerizable monomer in the present invention is a commonly used compound capable of radical polymerization, and refers to a compound containing one or more vinyl group, allyl group, acrylic group, or methacrylic group in the molecule. Specifically, alkyl (meth)acrylates, alkyl (meth) halides
(Meth)acrylic acid esters such as acrylate, siloxanylalkyl (meth)acrylate, hydroxyalkyl (meth)acrylate, polyethylene glycol (meth)acrylate, (meth)acrylic acid ester of polyhydric alcohol, vinyl (meth)acrylate, etc. , styrene derivatives, N-vinyl lactam, vinyl compounds such as vinyl (polyvalent) carboxylates, allyl (polyvalent) carboxylates,
Examples include allyl compounds such as allyl carbonate. More specifically, for example, styrene and methylstyrene, dimethylstyrene, chlorstyrene, dichlorostyrene, bromustyrene, p-chloromethylstyrene,
divinylbenzene, acrylic acid, methyl acrylate,
Ethyl acrylate, n-butyl acrylate, phenyl acrylate, phenoxyethyl acrylate, tetrahydrofurfuryl acrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate,
2-Acryloyloxyethylsuccinic acid, 2-acryloyloxyethyl phthalic acid, methacrylic acid, methyl methacrylate, ethyl methacrylate, n-butyl methacrylate, 2-ethylhexyl methacrylate, isobornyl methacrylate, benzyl methacrylate, phenyl methacrylate, dicyclopentanyl Methacrylate, dicyclopentenyl methacrylate, 2-methacryloyloxyethylsuccinic acid, 2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, 2-hydroxybutyl methacrylate, fumaric acid, maleic acid, itaconic acid and their esters, acrylonitrile, methacrylate Examples include lonitrile, N,N-dimethylacrylamide, N-vinyl-2-pyrrolidone, maleic anhydride, and N-substituted maleimide.

Furthermore, in order to increase the crosslinking density, ethylene glycol diacrylate, diethylene glycol diacrylate, triethylene glycol diacrylate, 1,6-hexanediol diacrylate, ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate , propylene glycol dimethacrylate, trimethylolpropane trimethacrylate, pentaerythritol triacrylate, 1,4-butanediol dimethacrylate, 1,6-hexanediol dimethacrylate, glycerin dimethacrylate, divinylbenzenediallyl phthalate, diethylene glycol bisallyl carbonate, etc. Polyfunctional monomers can also be used.

The amount of neodymium trisacetylacetonate dissolved in these polymerizable monomers is not uniform, and the amount of neodymium trisacetylacetonate to be added is adjusted as appropriate within the range that maintains transparency and exhibits anti-glare performance. Need to decide. In addition to being used alone, these polymerizable monomers
Two or more types can also be used in combination. Also,
A small amount of a heat stabilizer, an antioxidant, a dye, a coloring agent, an ultraviolet absorber, etc. can be added to the mixture consisting of a polymerizable monomer, neodymium trisacetylacetonate, and a polymerization initiator, if necessary. .

The polymerization of the present invention is carried out by heating or irradiation with active energy rays such as ultraviolet rays in the presence of a conventional polymerization initiator. As specific polymerization initiators, radical polymerization initiators are desirable, such as benzoyl peroxide, diisopropyl peroxydicarbonate,
t-Butylperoxy-2-ethylhexanoate, t
-butylperoxypivalate, t-butylperoxydiisobutyrate, t-butylperoxyisopropyl carbonate, lauroyl peroxide, azobisisobutyronitrile, azobis(2,4-dimethylvaleronitrile), etc. are used. In addition, in the case of irradiation with active energy rays, a photopolymerization initiator such as benzoin ether and a sensitizer are used as necessary. The amount of these initiators used is preferably 0.001 to 2 percent by weight based on the monomers used.

The contact lens of the present invention can be produced by injecting these monomers into the voids of a glass tube, a polypropylene or polytetrafluoroethylene tube, or a sheet, and heating them for thermal polymerization, or by exposing them to ultraviolet rays. Irradiation and photopolymerization are suitable. Also,
After this, if distortion occurs in the polymer due to polymerization shrinkage or polymerization heat, it is desirable to perform heat annealing to eliminate this.

[0017]

[Function] A contact lens made of a polymer obtained by polymerizing a mixture of a polymerizable monomer and neodymium trisacetylacetonate has sharp absorption in the wavelength range of 570 to 590 nm, which is the wavelength that is most dazzling to the human eye. It can selectively reduce only the amount of light and exhibits excellent anti-glare performance.

[0018]

[Example] This will be explained in more detail with reference to the following example.
The present invention is not limited to these. In addition, in the examples, parts represent parts by weight.

(Example 1) 95 parts by weight of methyl methacrylate, 4 parts by weight of triethylene glycol dimethacrylate, 1 part by weight of neodymium trisacetylacetonate, and 0.2 parts by weight of azobis(2,4-dimethylvaleronitrile) were thoroughly mixed. Then, this mixture was placed in a glass sealed tube, and the inside was repeatedly purged with nitrogen and degassed, and the tube was melt-sealed under vacuum. This sealed tube was heated in warm water at 30°C for 10 hours and at 40°C for 5 hours.
℃ for 5 hours, 60℃ for 3 hours, 70℃ for 3 hours,
Further, polymerization was carried out by heating at 100°C for 2 hours in an atmospheric furnace.
I got a round bar. The obtained rod was machined to produce contact lenses.

When the visible light transmittance of this contact lens was measured, the light transmittance at a wavelength of 580 nm was 60
%, while the light transmittance in other wavelength ranges was 90% or more, indicating excellent anti-glare performance.

(Example 2) 93 parts by weight of 2-hydroxyethyl methacrylate, 2 parts by weight of ethylene glycol dimethacrylate, 5 parts by weight of neodymium trisacetylacetonate, 0 parts by weight of azobis(2,4-dimethylvaleronitrile)
．． The mixture was placed in a glass sealed tube, the inside was repeatedly purged with nitrogen and degassed, and the mixture was melt-sealed under vacuum. This sealed tube was heated in warm water at 30°C for 10 hours, at 40°C for 5 hours, at 50°C for 5 hours, at 60°C for 3 hours, and at 70°C for 3 hours.
The mixture was heated for 1 hour and further heated at 100° C. for 2 hours in an air furnace to effect polymerization, thereby obtaining a round bar. The obtained rod was machined to obtain a contact lens. This lens was swollen in pure water, washed, and then immersed in physiological saline to absorb a predetermined amount of water and at the same time complete the elution of the eluate.

When the visible light transmittance of this contact lens was measured, the light transmittance at a wavelength of 580 nm was 20
%, while the light transmittance in other wavelength ranges was 85% or more, indicating excellent anti-glare performance.

(Example 3) 45 parts by weight of 2,2,2-trifluoroethyl methacrylate, 40 parts by weight of tris(trimethylsiloxy)silylpropyl methacrylate, 2
- 10 parts by weight of hydroxyethyl methacrylate, 3 parts by weight of ethylene glycol dimethacrylate, 2 parts by weight of neodymium trisacetylacetonate, and 0.2 parts by weight of azobis(2,4-dimethylvaleronitrile) are mixed well, and this mixture is made into a glass material. The tube was placed in a sealed tube, and the inside was repeatedly purged with nitrogen and degassed, followed by melt-sealing under vacuum. Place this sealed tube in warm water for 30 minutes.
10 hours at ℃, 5 hours at 40℃, 5 hours at 50℃, 60
℃ for 3 hours, 70℃ for 3 hours, and further heated in an atmospheric oven for 10 hours.
Polymerization was carried out by heating at 0° C. for 2 hours to obtain a round bar. The obtained rod was machined to produce contact lenses.

When the visible light transmittance of this contact lens was measured, the light transmittance at a wavelength of 580 nm was 45.
%, while the light transmittance in other wavelength ranges was 90% or more, indicating excellent anti-glare performance.

(Example 4) 70 parts by weight of 2,3-dihydroxypropyl methacrylate, 2 parts by weight of methyl methacrylate
7 parts by weight of ethylene glycol dimethacrylate, 1 part by weight of ethylene glycol dimethacrylate, 2 parts by weight of neodymium trisacetylacetonate, and 0.05 parts by weight of azobis(2,4-dimethylvaleronitrile), and this mixture was placed in a sealed glass tube. The interior was repeatedly purged with nitrogen and degassed, and then sealed under vacuum. This sealed tube was heated in warm water at 30°C for 10 hours and at 40°C for 5 hours.
Polymerization was carried out by heating at 0°C for 5 hours, at 60°C for 3 hours, at 70°C for 3 hours, and then at 100°C in an air furnace for 2 hours to obtain a round bar. The obtained rod was machined to obtain a contact lens. This lens was swollen in pure water, washed, and then immersed in physiological saline to absorb a predetermined amount of water and at the same time complete the elution of the eluate.

When the visible light transmittance of this contact lens was measured, the light transmittance at a wavelength of 580 nm was 45.
%, while the light transmittance in other wavelength ranges was 85% or more, indicating excellent anti-glare performance.

(Example 5) 70 parts by weight of 2,3-dihydroxypropyl methacrylate, 2 parts by weight of methyl methacrylate
6 parts by weight, 1 part by weight of ethylene glycol dimethacrylate, 3 parts by weight of neodymium trisacetylacetonate, 2,
0.05 parts by weight of 4,6-trimethylbenzoyldiphenylphosphine oxide was thoroughly mixed, and the mixture was degassed and replaced with nitrogen. This mixture was dropped into a glass mold shaped like a contact lens, and 80W/c
Ultraviolet rays were irradiated for 100 seconds at a distance of 10 cm using a high-pressure mercury lamp. The obtained contact lens was swollen in pure water, washed, and then immersed in physiological saline to absorb a predetermined amount of water and at the same time complete the elution of the eluate.

When the visible light transmittance of this contact lens was measured, the light transmittance at a wavelength of 580 nm was 30
%, while the light transmittance in other wavelength ranges was 85% or more, indicating excellent anti-glare performance.

(Comparative Example 1) When neodymium acetate, neodymium carbonate, neodymium chloride, neodymium nitrate, neodymium oxide, and neodymium methacrylate were used instead of neodymium trisacetylacetonate used in Example 1, all were dissolved in the monomer. I didn't.

[0030]

Effects of the Invention The trisacetylacetonatoneodymium of the present invention has excellent solubility in polymerizable monomers suitable as a material for contact lenses, so it can be obtained by polymerizing a mixture consisting of a polymerizable monomer and trisacetylacetonatoneodymium. Contact lenses made of these polymers can have high transparency and excellent anti-glare performance. Further, in the present invention, since there is a large degree of freedom in selecting the polymerizable monomer and the polymerization method, the physical properties of the resulting contact lens can be set widely depending on the intended use.

Claims (3)

[Claims] [Claim 1] A contact having anti-glare properties, comprising a polymer obtained by polymerizing a mixture of one or more polymerizable monomers and neodymium trisacetylacetonate as essential components. lens. 2. A contact lens having anti-glare performance according to claim 1, wherein the polymerizable monomer is a (meth)acrylic acid ester. Claim 3: Tris acetylacetonatoneodymium is 0.
The contact lens having anti-glare performance according to claim 1, characterized in that the amount is 1 to 20% by weight.