JPH1024097A - Soft ophthalmic lens and its manufacturing method - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a lens with a nonsticky surface for soft eyes by heat polymerizing a lens composition consisting of a polymeric component, which contains (meta) acrylate that imparts softness to the lens, and a polymerization initiator, fabricating a lens molding of the desired shape, and exposing it to light. SOLUTION: A lens for soft eyes is obtained by heat polymerizing an eye lens composition consisting of a polymeric component, which contains (meta) acrylate (monomer (A)) that imparts softness to the eye lens, and a polymerization initiator, and exposing an obtained eye lens molding of the desired shape to light. The monomer (A) as represented by formulae I, II. In the formulae, R' represents a -Ar group or a -O-Ar group, (n) 0 or an integer from 1 to 5, (s) a n integer from 1 to 15, and (t) an integer meeting 1 to (2s+1). One or two kinds or more of monomers (A) are used appropriately to impart sufficient softness to the obtained lens for soft eyes, the amount of monomers (A) in the polymeric component being normally 50wt% or more, preferably 60wt% or more.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a soft ophthalmic lens and a method for producing the same. More specifically, the present invention relates to a soft ophthalmic lens whose surface is modified and the surface has very little tackiness (stickiness) and a method for producing the same.

[0002]

2. Description of the Related Art Conventionally, as a soft ophthalmic lens, for example, a copolymer of (meth) acrylic acid ester has been used as a di (meth) acrylate.
Elastic intraocular lens made of a cross-linked acrylic resin material cross-linked with an acrylate ester (JP-A-1-158949)
JP-A-5-146461), a flexible intraocular composition comprising a copolymer obtained by copolymerizing a monomer mixture containing an aromatic (meth) acrylate and a crosslinkable monomer. Lens (JP-A-4-292609)
And so on.

[0003] However, the above-mentioned elastic intraocular lens and flexible intraocular lens have a drawback that their surfaces are easily sticky and are difficult to handle particularly during surgery.

Also, like the above-mentioned elastic intraocular lens and flexible intraocular lens, a soft contact lens made of a crosslinked acrylic resin material or copolymer obtained by using a (meth) acrylate and a crosslinkable monomer. However, they also have the disadvantage that, due to their sticky surfaces, they are inferior in wearing feeling and are liable to adhere with dirt.

Various studies have been made to improve the stickiness of the surfaces of the intraocular lens and the contact lens. For example, Japanese Patent Application Laid-Open No. 1-158949 describes that a fluoroacrylate is used as a (meth) acrylate to reduce such stickiness, and for a soft eye in which stickiness is reduced. Several lenses have also been proposed.

However, even when the above-mentioned fluoroacrylic acid ester is used, the stickiness of the surface of the soft intraocular lens which has yet to be obtained is not sufficiently reduced, and other soft ophthalmic lenses which have been proposed have been proposed. It is hard to say that the surface of the lens is also sufficiently reduced.

Accordingly, although the surface tackiness of the soft ophthalmic lens has some elements which are advantageous, there are many factors which are inconvenient in terms of handling. Therefore, the soft ophthalmic lens in which such stickiness is reduced as much as possible is disclosed. Development of a method for easily manufacturing an ophthalmic lens has been awaited.

[0008]

DISCLOSURE OF THE INVENTION The present invention has been made in view of the above prior art, and its surface is modified.
It is an object of the present invention to provide a soft ophthalmic lens having a very low surface stickiness and a method for producing the same.

[0009]

The present invention is obtained by thermally polymerizing a composition for an ophthalmic lens comprising a polymerization component containing a (meth) acrylate that imparts softness to an ophthalmic lens and a polymerization initiator. A soft ophthalmic lens obtained by irradiating a molded ophthalmic lens having a desired shape with light, and an ophthalmic lens comprising a polymerization component and a polymerization initiator containing a (meth) acrylate that imparts softness to the ophthalmic lens The present invention relates to a method for producing a soft ophthalmic lens, which comprises thermally polymerizing a composition to produce an ophthalmic lens molded body having a desired shape and irradiating the ophthalmic lens molded body with light.

[0010]

BEST MODE FOR CARRYING OUT THE INVENTION As described above, the soft ophthalmic lens of the present invention comprises a polymer component containing (meth) acrylate (hereinafter referred to as a monomer (A)) which imparts softness to the ophthalmic lens. It can be obtained by irradiating light to an ophthalmic lens molded article having a desired shape obtained by thermally polymerizing an ophthalmic lens composition comprising an initiator.

The monomer (A) used in the present invention is a component that imparts softness to the finally obtained ophthalmic lens.

Representative examples of the monomer (A) include, for example, benzyl acrylate, phenyl acrylate,
General formula (I) such as phenylethyl acrylate and 2-phenoxyethyl acrylate:

[0013]

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Wherein R ¹ is an —Ar group (Ar represents an aromatic ring in which a hydrogen atom may be substituted by an alkyl group)
Or an aromatic ring-containing acrylate, trifluoroethyl acrylate, tetrafluoropropyl acrylate, tetrafluoropentyl acrylate represented by a -O-Ar group (Ar is the same as described above), and n represents 0 or an integer of 1 to 5; Hexafluorobutyl acrylate, hexafluorohexyl acrylate, hexafluorobis (trifluoromethyl) pentyl acrylate, hexafluorobutyl acrylate, hexafluoroisopropyl acrylate, heptafluorobutyl acrylate, octafluoropentyl acrylate, nonafluoropentyl acrylate, dodecafluoroheptyl acrylate , Dodecafluorooctyl acrylate, tridecafluorooctyl acrylate, tridecafluoroheptyl acryle Door, hexadecafluoro-decyl acrylate, heptadecafluorodecyl acrylate, octadecanol fluoro-undecyl acrylate, nona decafluorooctanoate undecyl acrylate, formula, such as Eiko fluoro-dodecyl acrylate (II):

[0015]

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Wherein s is an integer of 1 to 15, and t is 1 to
(Indicating an integer satisfying (2s + 1)), a fluorine atom-containing alkyl acrylate, methyl acrylate, ethyl acrylate, propyl acrylate, n-
Butyl acrylate, isobutyl acrylate, pentyl acrylate, hexyl acrylate, heptyl acrylate, nonyl acrylate, stearyl acrylate, 2-ethylhexyl acrylate, n-octyl acrylate, tridecyl acrylate, lauryl acrylate, cyclopentyl acrylate, cyclohexyl acrylate, 2-ethoxyethyl acrylate, 3-
Linear, branched or cyclic alkyl acrylates such as ethoxypropyl acrylate, 2-methoxyethyl acrylate, and 3-methoxypropyl acrylate;
Hydroxyethyl acrylate, hydroxypropyl acrylate, hydroxyalkyl acrylate such as hydroxybutyl acrylate, dihydroxyalkyl acrylate such as dihydroxypropyl acrylate,
Hydroxyl-containing acrylates such as polyethylene glycol monoacrylates such as diethylene glycol monoacrylate and propylene glycol monoacrylate, trimethylsiloxydimethylsilylmethyl acrylate, trimethylsiloxydimethylsilylpropyl acrylate, methylbis (trimethylsiloxy) silylpropyl acrylate, tris (trimethylsiloxy) silylpropyl Acrylate, mono [methylbis (trimethylsiloxy)
[Siloxy] bis (trimethylsiloxy) silylpropyl acrylate, tris [methylbis (trimethylsiloxy) siloxy] silylpropyl acrylate, methylbis (trimethylsiloxy) silylpropylglyceroylacrylate, tris (trimethylsiloxy) silylpropylglyceroylacrylate, mono [methylbis ( Trimethylsiloxy) siloxy] bis (trimethylsiloxy) silylpropylglyceroylacrylate, trimethylsilylethyltetramethyldisiloxypropylglyceroylacrylate, trimethylsilylmethylacrylate, trimethylsilylpropylacrylate,
Trimethylsilylpropyl glyceroyl acrylate,
Trimethylsiloxydimethylsilylpropyl glyceroyl acrylate, methyl bis (trimethylsiloxy) silylethyltetramethyldisiloxymethyl acrylate, tetramethyltriisopropylcyclotetrasiloxanylpropyl acrylate, tetramethyltriisopropylcyclotetrasiloxybis (trimethylsiloxy) silylpropyl acrylate Acrylic acid esters such as silicon-containing acrylates; acrylic acid; linear or branched having 7 to 18 carbon atoms such as lauryl methacrylate, nonyl methacrylate, stearyl methacrylate, n-octyl methacrylate, 2-ethylhexyl methacrylate, tridecyl methacrylate; Methacrylic acid esters such as linear alkyl methacrylates; These may be used alone or in admixture of two or more.

Among the monomers (A), the obtained soft ophthalmic lens has excellent shape recovery properties.
Acrylic esters are preferred.

One or more of the above-mentioned monomers (A) may be appropriately used so that the obtained soft ophthalmic lens can be sufficiently softened. The amount is usually at least 50% by weight, preferably 6% by weight.
It is desirable to use it so that it may be 0% by weight or more.

In the present invention, one of the polymerization components
The monomer (A) may be present in an amount of 00% by weight. However, as described below, for example, a polymerizable monomer copolymerizable with the monomer (A) (hereinafter, referred to as a monomer (B)) may be used as described below. It may be contained in the polymerization component. In this case, the amount of the monomer (A) in the polymerization component is determined in consideration of the desired properties of the obtained soft ophthalmic lens, and the like.
For example, the total amount with the monomer (B) is 100% by weight.
It may be appropriately adjusted so that

The polymerization component used in the present invention contains the monomer (A). As described above, in addition to the monomer (A), depending on the desired properties of the soft ophthalmic lens. , A monomer (B) and the like.

Representative examples of the monomer (B) include, for example, methyl methacrylate, ethyl methacrylate,
Examples thereof include alkyl methacrylates having 1 to 6 carbon atoms in an alkyl group such as butyl methacrylate and cyclohexyl methacrylate; aromatic ring-containing methacrylates such as phenoxyethyl methacrylate, phenylethyl methacrylate, and phenyl methacrylate; styrene derivatives; and macromonomers.

Examples of the styrene derivative include styrene; alkylstyrenes such as α-methylstyrene, methylstyrene, ethylstyrene, propylsstyrene, butylstyrene, and pentylstyrene, methyl-α-methylstyrene, ethyl-α-methyl Alkyl-substituted styrene such as alkyl-α-methylstyrene such as styrene, propyl-α-methylstyrene, butyl-α-methylstyrene and pentyl-α-methylstyrene; for example, tris (trimethylsiloxy) silylstyrene, methylbis (trimethylsiloxy) ) Silylstyrene, (trimethylsiloxy) dimethylsilylstyrene,
Tris (trimethylsiloxy) siloxydimethylsilylstyrene, [methylbis (trimethylsiloxy) siloxy] dimethylsilylstyrene, (trimethylsiloxy)
Dimethylsilylstyrene, heptamethyltrisiloxanylstyrene, nonamethyltetrasiloxanylstyrene,
Pentadecamethylheptasiloxanyl styrene, heneicosamethyl decasiloxanyl styrene, heptacosamethyl tridecasiloxanyl styrene, hentriacontamethylpentadecasiloxanyl styrene, trimethylsiloxypentamethyldisiloxymethylsilyl styrene,
Tris (pentamethyldisiloxy) silylstyrene, tris (trimethylsiloxy) siloxybis (trimethylsiloxy) silylstyrene, methylbis (heptamethyltrisiloxy) silylstyrene, tris [methylbis (trimethylsiloxy) siloxy] silylstyrene, trimethylsiloxybis [tris (Trimethylsiloxy)
Siloxy] silylstyrene, heptakis (trimethylsiloxy) trisilylstyrene, nonamethyltetrasiloxyundecylmethylpentasiloxymethylsilylstyrene, tris [tris (trimethylsiloxy) siloxy]
Silyl styrene, [tris (trimethylsiloxyhexamethyl)] tetrasiloxy [tris (trimethylsiloxy) siloxy] trimethylsiloxysilylstyrene, nonakis (trimethylsiloxy) tetrasilylstyrene,
General formulas such as methylbis (tridecamethylhexasiloxy) silylstyrene, heptamethylcyclotetrasiloxanylstyrene, heptamethylcyclotetrasiloxybis (trimethylsiloxy) silylstyrene, tripropyltetramethylcyclotetrasiloxanylstyrene, trimethylsilylstyrene (III):

[0023]

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Wherein p is an integer of 1 to 15, q is 0 or 1, and r is an integer of 1 to 15; silicon-containing styrene derivatives such as pentafluorostyrene and trifluorostyrene , P-vinylbenzoic acid-2,2,2-trifluoro-1- (trifluoromethyl) ethyl ester, (p-vinylphenyl) acetic acid-2,2,2-trifluoro-1- (trifluoromethyl) And fluorine-containing styrene derivatives such as esters.

The macromonomer is, for example, a compound represented by the following general formula:

[0026]

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(Wherein a represents 28 on average) a urethane bond-containing polysiloxane macromonomer represented by the following general formula:

[0028]

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(Where b represents an average of 30), such as a polysiloxane macromonomer represented by the general formula (I
V): A ¹ -U ¹ -S ¹ -U ² -A ² (IV) (where A ¹ is a general formula: Y ¹ -R ^2- (wherein Y ¹ is an acryloyloxy group or a methacryloyloxy group) , A vinyl group or an allyl group, and R ² has 2 to 2 carbon atoms.
A ² represents a linear or branched alkylene group; A ² represents a general formula: —R ³ —Y ² (wherein Y ² represents an acryloyloxy group, a methacryloyloxy group, a vinyl group or an allyl group) Group, R ³ has 2 to 2 carbon atoms
U ¹ represents a general formula: —X ¹ —E ¹ —X ² —R ⁴ — (wherein X ¹ represents a covalent bond, an oxygen atom Or 1 to 6 carbon atoms
An alkylene glycol group, E ¹ is a —CONH— group (where X ¹ is a covalent bond and E ¹ forms a urethane bond with X ² ) or a saturated or unsaturated aliphatic group; A divalent group derived from a diisocyanate selected from the group of alicyclic and aromatic groups (where X ¹ is an oxygen atom or an alkylene glycol group having 1 to 6 carbon atoms, and E ¹ is X It forms a urethane bond between the ¹ and X ^2); X ² is an alkylene glycol group having 1 to 6 carbon oxygen atom or a carbon; R ⁴ is 1 to carbon atoms
S ¹ represents a linear or branched alkylene group);

[0030]

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(Wherein R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ are each independently an alkyl group having 1 to 6 carbon atoms, a fluorine-substituted alkyl group or a phenyl group, and K is 1 to
A group represented by an integer of 50, L is an integer satisfying 0 to (50-K); U ² is a general formula: —R ¹¹ —X ³ —E ² —X ⁴ — (where R ¹¹ is A linear or branched alkylene group having 1 to 6 carbon atoms, X ⁴ is a covalent bond, an oxygen atom or an alkylene glycol group having 1 to 6 carbon atoms, and X ³ is an oxygen atom or an alkylene glycol group having 1 to 6 carbon atoms , E ² −
A CONH- group (where X ⁴ is a covalent bond and E ² forms a urethane bond with X ³ ) or a saturated or unsaturated aliphatic, alicyclic and aromatic A divalent group derived from a diisocyanate selected from the group (provided that X ⁴ represents an oxygen atom or
Wherein E ² is X ⁴ and X ³
And a polymerizable group represented by) is bonded to the siloxane main chain via one or two urethane bonds, such as a polysiloxane macromonomer. And polysiloxane macromonomer.

The monomers (B) can be used alone or in combination of two or more.

Among the monomers (B), for example, in order to increase the mechanical strength of the obtained soft ophthalmic lens, for example, the silicon-containing (meth) acrylate,
It is preferable to use a silicon-containing styrene derivative, a macromonomer, or the like.

For adjusting the hardness of the obtained soft ophthalmic lens, for example, by further improving the softness or imparting the hardness, it is preferable to use, for example, the above-mentioned methyl methacrylate, styrene, alkyl-substituted styrene and the like. preferable.

For example, in order to improve the stain resistance, such as anti-lipid stain resistance, of the obtained soft ophthalmic lens, it is preferable to use, for example, the above-mentioned fluorine-containing styrene derivative.

The amount of the monomer (B) in the polymerization component is
As described above, in consideration of the desired properties of the obtained soft ophthalmic lens and the like, the total amount with the monomer (A) is 1
The amount may be appropriately adjusted so as to be 00% by weight. However, in order for the effect of imparting softness to the ophthalmic lens by the monomer (A) to be sufficiently exhibited, the amount of the monomer (B) must be adjusted. It is desirable that the content be 50% by weight or less, preferably 40% by weight or less of the polymerization component.

Further, in the present invention, in order to impart a suitable mechanical strength to the obtained soft ophthalmic lens, it is preferable to include a crosslinkable monomer in the polymerization component.

As the crosslinkable monomer, for example, 2
General formulas such as 2-hydroxypropylene glycol di (meth) acrylate such as -hydroxypropylene glycol acrylate methacrylate, di (2-hydroxypropylene glycol) di (meth) acrylate, and tri (2-hydroxypropylene glycol) di (meth) acrylate (V):

[0039]

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Wherein R ¹² and R ¹³ are each independently a hydrogen atom or a methyl group, and m is an integer of 1 to 10, diallyl fumarate, allyl (meth) acrylate, trimethylol Propane tri (meth) acrylate, ethylene glycol di (meth)
Examples thereof include acrylate, butadiene glycol di (meth) acrylate, divinylbenzene, and vinylbenzene (meth) acrylate, and these can be used alone or as a mixture of two or more.

In the general formula (V), m is 1
It is an integer of from 10 to 10. However, it is preferable that m is an integer of from 1 to 3 from the viewpoint that flexibility suitable for a soft ophthalmic lens is imparted.

Among the crosslinkable monomers, the compound represented by the above general formula (V) and ethylene glycol di (meth) ate are effective in imparting appropriate mechanical strength to the obtained soft ophthalmic lens. Acrylates are preferred.

The amount of the crosslinkable monomer is 0.1 part or more, preferably 0.1 part, based on 100 parts (parts by weight, hereinafter the same) of the total amount of the polymerization component in order to sufficiently exhibit the crosslinking effect.
It is desirable to adjust the amount to 2 parts or more, and in order to eliminate the possibility that the flexibility and elasticity of the obtained soft ophthalmic lens is reduced, 10 parts or less, preferably 6 parts or less, per 100 parts of the total amount of the polymerization component. It is desirable to make adjustments so as to be less than or equal to the number of parts.

The composition for an ophthalmic lens used in the present invention comprises the above-mentioned polymerization component and a polymerization initiator,
In the production method of the present invention, first, the composition for an ophthalmic lens is thermally polymerized.

As the polymerization initiator, for example, a thermal polymerization initiator and / or a photopolymerization initiator are suitably used.

Representative examples of the thermal polymerization initiator include, for example, azobisisobutyronitrile, azobisdimethylvaleronitrile, benzoyl peroxide, t-butyl hydroperoxide, cumene hydroperoxide, dicumyl peroxide, dicumyl peroxide, -T-butyl peroxide, lauroyl peroxide and the like, and these can be used alone or as a mixture of two or more.

Considering the reduction of residual monomers and the improvement of moldability by increasing the polymerization rate, the amount of the thermal polymerization initiator is preferably 0.1 to 100 parts of the total amount of the polymerization components.
The amount is preferably at least 01 part, more preferably at least 0.1 part, and the polymerization rate is excessively increased so that the molecular weight is reduced and the mechanical strength of the ophthalmic lens molded body is not reduced accordingly. In view of this, it is desirable that the amount be 5 parts or less, preferably 2 parts or less based on 100 parts of the total amount of the polymerization components.

Representative examples of the photopolymerization initiator include, for example, methyl orthobenzoyl benzoate, methyl benzoyl formate, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzoin-n-
Benzoin-based photopolymerization initiators such as butyl ether; 2-
Hydroxy-2-methyl-1-phenylpropane-1-
On, p-isopropyl-α-hydroxyisobutylphenone, pt-butyltrichloroacetophenone,
2,2-dimethoxy-2-phenylacetophenone,
α, α-dichloro-4-phenoxyacetophenone,
N, N-tetraethyl-4,4-diaminobenzophenone, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone-1, 1-hydroxycyclohexylphenyl ketone, 1-phenyl-1,2-
Phenone-based photopolymerization initiators such as propanedione-2- (o-ethoxycarbonyl) oxime; thioxanthone-based photopolymerization initiators such as 2-chlorothioxanthone and 2-methylthioxanthone; tetraethylthiuram monosulfide, tetramethylthiuram Thiuram-based photopolymerization initiators such as monosulfide, tetraethylthiuram disulfide and tetramethylthiuram disulfide; dibenzosubalone; 2-ethylanthraquinone; benzophenone acrylate; benzophenone; benzyl;
These can be used alone or in combination of two or more.

When the photopolymerization initiator is in a liquid state, for example, it acts as a solvent when the composition for an ophthalmic lens is thermally polymerized. The flowability of the composition for ophthalmic lenses in a mold having is enhanced, considering that the ophthalmic lens molded body having the desired shape can be more easily obtained, the total amount of the polymerization component is 100 parts. 0.1 part or more, preferably 0.5 part or more. Also, as in the case of the thermal polymerization initiator, the polymerization rate is excessively increased, and the molecular weight is decreased. Considering that the mechanical strength of the ophthalmic lens molded article is not reduced, the amount is preferably 20 parts or less, and more preferably 5 parts or less, based on 100 parts of the total amount of the polymerization component.

In the production method of the present invention, an ophthalmic lens composition comprising a polymerization component and a polymerization initiator is thermally polymerized to produce an ophthalmic lens molded body having a desired shape.
Further, since the ophthalmic lens molded body is irradiated with light, the polymerization initiator is more efficiently promoted, and in order to more effectively promote the surface modification of the ophthalmic lens molded body by light irradiation, the polymerization initiator is used. It is preferable that the composition contains a thermal polymerization initiator and a photopolymerization initiator.

As described above, when the thermal polymerization initiator and the photopolymerization initiator are used in combination, the total amount of the two components must be 10% in order to allow the polymerization reaction to proceed at a sufficient speed.
It is desirable to adjust the amount to be 0.11 part or more, preferably 0.6 part or more with respect to 0 part. In order to eliminate the possibility that bubbles are generated in the obtained soft ophthalmic lens, the total amount of the polymerization component is required. It is desirable that the amount is adjusted to 25 parts or less, preferably 7 parts or less for 100 parts.

Further, in the present invention, when the ophthalmic lens molded article is irradiated with light, the light is easily absorbed, and the polymerization is accelerated by the light irradiation. In order to do so, it is preferable that the composition for an ophthalmic lens contains a light absorber.

The light absorbing agent may be appropriately selected and used according to the type of light used for light irradiation. For example, when the light irradiation is ultraviolet irradiation, it is preferable to use an ultraviolet absorber as a light absorber.

Representative examples of the ultraviolet absorber include, for example, 2-hydroxy-4-methoxybenzophenone,
Benzophenones such as -hydroxy-4-octoxybenzophenone, 2- (2'-hydroxy-5'-methacryloxyethyleneoxy-t-butylphenyl)-
5-methyl-benzotriazole, 2- (2'-hydroxy-5'-methylphenyl) benzotriazole,
-Chloro-2 (3'-tert-butyl-2'-hydroxy-
Benzotriazoles such as 5'-methylphenyl) benzotriazole, salicylic acid derivatives, hydroxyacetophenone derivatives and the like. In addition, a reactive ultraviolet absorber having the same chemical structural portion as those ultraviolet absorbers and having a portion capable of polymerizing with the polymerization component used in the present invention can also be used. These can be used alone or in combination of two or more.

The amount of the light absorbing agent is 0.01 part or more, preferably 100 parts or more, based on 100 parts of the total amount of the polymerization component, in order to sufficiently promote the polymerization near the surface of the ophthalmic lens molded article. It is desirable to adjust so as to be 0.05 part or more, and bubbles are generated when the composition for ophthalmic lenses is thermally polymerized, the polymerization rate is reduced, or a sufficient degree of polymerization cannot be obtained. In order to eliminate the risk, it is desirable that the amount is adjusted to 5 parts or less, preferably 3 parts or less based on 100 parts of the total amount of the polymerization components.

Further, in the present invention, in order to color the obtained soft ophthalmic lens, it is preferable that a dye is contained in the ophthalmic lens composition. As such a dye, a yellow or orange dye is desirable, for example, in the case where blue vision caused in aphakic patients after cataract surgery is corrected by an intraocular lens.

Representative examples of the dye include oil-soluble dyes such as CI Solvent Yellow and CI Solvent Orange described in Color Index (CI), and CI Disperse Yellow.
e Orange), CI Disperse Orange (Di)
disperse dyes such as Sperse Orange) and vat dyes. In addition, reactive dyes having the same chemical structure as those dyes and having a portion capable of polymerizing with the polymerization component used in the present invention can also be used. These can be used alone or in combination of two or more.

The amount of the pigment is 0.001 part or more, preferably 0.0%, based on 100 parts of the total amount of the polymerizable component in order to sufficiently color the obtained soft ophthalmic lens.
It is desirable to adjust the amount to 1 part or more, and in order to eliminate the possibility of excessively deep coloring, the amount is adjusted to 5 parts or less, preferably 3 parts or less based on 100 parts of the total amount of the polymerization component. It is desirable.

In the production method of the present invention, as described above, the polymerization method comprises the monomer (A) and, if necessary, the polymerization component containing the monomer (B) and a crosslinkable monomer and a polymerization initiator. An ophthalmic lens molded body having a desired shape is produced by thermally polymerizing an ophthalmic lens composition containing an absorbent, a dye, and the like.

The method for thermally polymerizing the composition for ophthalmic lens is not particularly limited. However, in order to perform the molding in a short time and stably, the composition for ophthalmic lens is preferably used in an amount of 30 to 10%.
It is preferable to heat at a temperature of about 0 ° C. for a time of about 2 to 40 hours. Further, the polymerization temperature is 40 to 70 ° C., preferably 50 to 60 ° C. in order to improve moldability and prevent generation of bubbles and the like.
C. is desirable. In order to minimize the residual monomer, the polymerization time is desirably 16 hours or more.

Further, in order to further reduce the amount of the residual monomer and to complete the polymerization more sufficiently, a method of gradually increasing the temperature to about 120 ° C. at a rate of 5 to 20 ° C./hour is employed. It is also possible.

In the thermal polymerization, a bulk polymerization method, a solution polymerization method using a solvent or the like may be employed, or another method may be employed.

The molding method for producing an ophthalmic lens molded body having a desired shape is not particularly limited, and for example, a cutting method, a mold method, or the like can be employed.

In the above-mentioned cutting method, the composition for ophthalmic lens is thermally polymerized in an appropriate mold or container which is easy to mold, and a material (polymer) such as a rod, a block or a plate is obtained. This is a method of processing such a polymer into a molded ophthalmic lens having a desired shape by using a lathe or the like and performing mechanical processing such as cutting or polishing.

In the mold method, a molded article (polymer) is obtained by thermally polymerizing an ophthalmic lens composition in a mold corresponding to a desired shape of a soft ophthalmic lens such as a contact lens or an intraocular lens. In addition, this is a method of obtaining a molded ophthalmic lens having a desired shape by mechanically performing a finishing process as necessary.

Since a polymer obtained by thermally polymerizing the composition for an ophthalmic lens usually shows softness at ordinary temperature, a mold method is suitably employed. When mechanical processing such as cutting is performed, it is preferable that the obtained polymer is subjected to mechanical processing by cooling or the like in order to suppress a decrease in workability.

There are no particular restrictions on the mold or container used for thermally polymerizing the ophthalmic lens composition. For example, glass and plastics such as polyethylene, polypropylene and polyacetal can be used.

By irradiating the thus obtained ophthalmic lens molded body having a desired shape with light, a soft ophthalmic lens such as a contact lens or an intraocular lens can be obtained.

In the present invention, one of the major features is that light is applied to the ophthalmic lens molded body having a desired shape obtained by thermal polymerization.

When the polymerization is to be promoted again by heating as in the prior art, the polymerization is not promoted as expected because the components which can be polymerized by heat have already been deactivated, and effective tackiness is not obtained. Reduction cannot be expected. In contrast,
In the present invention, the light energy by the light irradiation activates the activatable component again, promotes the radical polymerization again, and the light irradiation is more direct near the surface of the ophthalmic lens molded body. The polymerization proceeds further near the surface of the molded ophthalmic lens, and the vicinity of the surface is hardened, so that the tackiness is substantially reduced substantially.

There is no particular limitation on the method of irradiating the ophthalmic lens molded body with light. For example, ultraviolet irradiation such as an ultra-high pressure mercury lamp, a high pressure mercury lamp, a low pressure mercury lamp, a metal halide lamp, an indium lamp, a xenon lamp, etc. It is possible to adopt a method in which an ophthalmic lens molded body is installed in the apparatus and light is irradiated.

The type of light applied to the ophthalmic lens molded body is not particularly limited, as long as it can sufficiently promote the polymerization reaction (curing reaction) near the surface of the ophthalmic lens molded body.

A typical example of the irradiation light is, for example, ultraviolet light. Ultraviolet light is preferred because it has a large light energy, so that the curing reaction is sufficiently promoted in a relatively short irradiation time. Among them, the irradiation intensity is 0.01 to 30 μW / cm ² , preferably 0.1 to 5 μW
Ultraviolet light emitted from a low-pressure mercury lamp of W / cm ²
It is preferable in terms of preventing deterioration of the ophthalmic lens molded article and accelerating the curing reaction in a short time.

The irradiation time at the time of light irradiation can be arbitrarily set according to, for example, the composition of the ophthalmic lens composition, the performance of the light irradiation device, and the like. What is necessary is just to adjust suitably so that it may remain near the surface of the ophthalmic lens molded body and the surface tackiness is sufficiently reduced. Since the irradiation time varies depending on the irradiation intensity, it cannot be determined unconditionally,
Usually, it is preferably about several seconds to one hour, especially about 30 seconds to 20 minutes.

When the ophthalmic lens composition used for obtaining the ophthalmic lens molded article contains a light absorbing agent, the light absorbing agent absorbs the irradiated light, Is hardly transmitted, and light energy is easily provided only near the surface of the ophthalmic lens molded body, so that adverse effects (damage) on the inside of the ophthalmic lens molded body can be reduced, and the allowable irradiation time width Becomes wider.

Among the above molding methods, when the mold method is employed, when a mold made of a material that transmits light to be irradiated, such as a polypropylene mold or a polyacetal mold, is used. After the polymerization is completed, the mold for the ophthalmic lens can be placed in the light irradiation device as it is without releasing the mold for the ophthalmic lens, and the light irradiation can be performed. Further, in this case, since the vicinity of the surface of the ophthalmic lens molded body is hardened, there is an advantage that the releasing operation is easier.

Further, in the present invention, when an intraocular lens is used as an ophthalmic lens, a supporting portion for the lens is manufactured separately from the lens, and for example, a hole is formed in the lens, and the supporting portion formed in the hole is formed. The support part may be attached to the lens later, or the lens and the support part may be simultaneously (integrally)
It may be molded.

According to the production method of the present invention, a soft ophthalmic lens whose surface is modified and the surface is extremely non-sticky can be easily obtained. An intraocular lens that is easy to wear, and a contact lens that is excellent in wearing feeling and hardly adheres dirt.

[0079]

Next, the soft ophthalmic lens of the present invention and a method for producing the same will be described in more detail with reference to Examples. However, the present invention is not limited to these Examples.

Examples 1 to 9 A composition for ophthalmic lenses having the composition shown in Table 1 was mixed, and this was mixed with a polypropylene mold having a shape corresponding to an intraocular lens (optical part) having a diameter of 6 mm and a thickness of 1 mm. Injected into. Then, the mold was placed at 50 ° C. in a nitrogen gas atmosphere.
The composition for an ophthalmic lens was thermally polymerized for 16 hours in an oven described above to obtain a polymer (molded ophthalmic lens).

Next, the mold was placed under an ultraviolet lamp with the ophthalmic lens molded article still in it, and irradiated with ultraviolet light for 7 minutes. After the completion of the ultraviolet irradiation, the molded body was released from the mold. The molded body was immersed in ethanol at 50 ° C. for 24 hours to extract residual monomers, and then dried in a vacuum oven at 50 ° C. for 16 hours to obtain a transparent 6 mm in diameter and 1 mm thick transparent. Obtained a soft intraocular lens (optical part).

Comparative Examples 1 to 9 In the same manner as in Examples 1 to 9, except that the step of irradiating the molded ophthalmic lens in the mold with ultraviolet rays was not performed, the diameter of the molded ophthalmic lens was about 6 mm. About 1m thick
m transparent soft intraocular lens (optical part) was obtained.

The abbreviations in Table 1 indicate the following.

(Monomer (A)) POEA: 2-phenoxyethyl acrylate 3FEA: 2,2,2-trifluoroethyl acrylate EA: ethyl acrylate iBuA: isobutyl acrylate (monomer (B)) CHMA: cyclohexyl methacrylate iBuMA: isobutyl methacrylate PhMA: phenyl methacrylate (crosslinkable monomer) EDMA: ethylene glycol dimethacrylate GAMA: 2-hydroxypropylene glycol acrylate methacrylate (ultraviolet absorber): 2- (2′-hydroxy-5′-methacryloxyethyleneoxy-t-butylphenyl) )
-5-methyl-benzotriazole (thermal polymerization initiator) A: 2,2'-azobis (isobutyronitrile) B: 2,2'-azobis (2,4-dimethylvaleronitrile) (photopolymerization initiator) A: 2-hydroxy-2-methyl-1-phenylpropan-1-one B: 2,2-dimethoxy-2-phenylacetophenone Next, the intraocular lens (optical part) obtained in Examples 1 to 9
As a physical property, the tackiness (stickiness) was examined according to the following method. Table 1 shows the results.

[Adhesiveness (Stickiness)] Two intraocular lenses (optical parts) obtained in Examples 1 to 9 were prepared, and these two intraocular lenses (optical parts) were superimposed on each other. And the intraocular lens (optical part) obtained in Comparative Examples 1 to 9 in which the ultraviolet ray was not irradiated,
Two pieces were similarly superimposed and held for one minute, respectively, and evaluated based on the following evaluation criteria.

(Evaluation Criteria) A: In comparison with the intraocular lens (optical part) of the comparative example, the intraocular lens (optical part) of the example has improved tackiness. B: In comparison with the intraocular lens (optical part) of the comparative example, the tackiness of the intraocular lens (optical part) of the example is almost the same. C: The intraocular lens (optical part) of the example is more sticky than the intraocular lens (optical part) of the comparative example.

[0087]

[Table 1]

From the results shown in Table 1, the intraocular lenses (optical parts) of Examples 1 to 9 are all comparative examples 1 to 9, respectively.
As compared with the intraocular lens (optical part) No. 9, the stickiness was improved, and it can be seen that an intraocular lens whose surface was modified by irradiation with ultraviolet rays was obtained.

[0089]

According to the production method of the present invention, a soft ophthalmic lens whose surface is modified and whose surface has very little stickiness can be easily obtained.

As described above, since the surface of the soft ophthalmic lens of the present invention is modified and the surface is extremely non-sticky, for example, an intraocular lens or a lens which can be easily handled at the time of surgery or the like. It is possible to provide a contact lens which is excellent in wearing feeling and hardly adheres dirt.

Claims (10)

[Claims] 1. A method for imparting softness to an ophthalmic lens (meth)
A soft ophthalmic lens obtained by thermally irradiating an ophthalmic lens molded article having a desired shape obtained by thermally polymerizing an ophthalmic lens composition comprising a polymerization component containing an acrylate and a polymerization initiator. 2. A method for imparting softness to an ophthalmic lens (meth)
The soft ophthalmic lens according to claim 1, wherein the acrylate is an acrylate ester. 3. The soft ophthalmic lens according to claim 1, wherein the polymerization initiator contains a thermal polymerization initiator and a photopolymerization initiator. 4. The soft ophthalmic lens according to claim 1, wherein the ophthalmic lens composition contains a light absorbing agent. 5. The soft ophthalmic lens according to claim 4, wherein the light irradiation is ultraviolet irradiation, and the light absorber is an ultraviolet absorber. 6. A method for imparting softness to an ophthalmic lens (meth)
An ophthalmic lens composition comprising an acrylate-containing polymerization component and a polymerization initiator is thermally polymerized to produce an ophthalmic lens molded body having a desired shape, and the ophthalmic lens molded body is irradiated with light. Method for manufacturing a soft ophthalmic lens. 7. A method for imparting softness to an ophthalmic lens (meth)
The method for producing a soft ophthalmic lens according to claim 6, wherein the acrylate is an acrylic ester. 8. The method for producing a soft ophthalmic lens according to claim 6, wherein the polymerization initiator contains a thermal polymerization initiator and a photopolymerization initiator. 9. The method for producing a soft ophthalmic lens according to claim 6, wherein the ophthalmic lens composition contains a light absorbing agent. 10. The method for producing a soft ophthalmic lens according to claim 9, wherein the light irradiation is ultraviolet irradiation, and the light absorber is an ultraviolet absorber.