JPH08283345A - Water-containing soft contact lens - Google Patents

Abstract

PURPOSE: To obtain a water-containing contact lens having excellent oxygen permeability and good mechanical strengths and flexibility irrespectively of its water content. CONSTITUTION: A water-containing soft contact lens made from a polymer obtained by polymerizing a fluorostyrene derivative represented by the formula (wherein R<1> is hydrogen or methyl; m is an integer of 1-3; and n is 0 or an integer of 1-7) and N,N-dimethyl(meth)acrylamide.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a hydrous soft contact lens. More specifically, the present invention relates to a water-containing soft contact lens having excellent oxygen permeability, good mechanical strength and flexibility without depending on the water content.

[0002]

2. Description of the Related Art Conventionally, contact lens materials include hard materials and soft materials, and in general, soft materials are preferably used in order to obtain contact lenses having a good wearing feeling. The soft material includes a water-containing material that absorbs water, swells, and softens, and a substantially non-water-containing material.

In order to wear contact lenses safely and for a long time, it is necessary to supply more oxygen to the cornea, which increases the oxygen permeability of the material,
A method of substantially increasing the oxygen permeation amount by reducing the thickness of the lens is adopted.

The water-containing material is one in which the material itself does not allow oxygen to permeate, but is imparted with oxygen permeability by water containing water.
The British Contact Lens Association "(Journalof the Britis
h Contact Lens Associatio
n), 17 [1] (1994), p. 11-18, "Oxygen Permeability of Contact Lens Materials: A. 1993 Update" (OXYGEN PERMEABILITY
OF CONTACT LENS MATERIAL
S: A 1993 UPDATE) (Fat
t) and by Ruben) (hereinafter Fat
In general, it is known that oxygen permeability depends on the water content. Therefore, in order to increase the oxygen permeability of the contact lens, a material having a high water content is required, but in general, as the water content of the material increases, the mechanical strength of the material decreases and other disadvantages occur. .

Further, in the case of a low water content material, attempts have been made to make the lens thickness smaller and to substantially increase the oxygen transmission amount, but a thin type which can supply a sufficient oxygen transmission amount. Obtaining a lens is technically difficult.

[0006]

DISCLOSURE OF THE INVENTION The present invention has been made in view of the above-mentioned prior art, and does not depend on the water content, and has excellent oxygen permeability, good mechanical strength and flexibility. An object of the present invention is to provide a soft contact lens.

[0007]

The present invention has the general formula (I):

[0008]

Embedded image

(Wherein R ¹ is a hydrogen atom or a methyl group,
m is an integer of 1 to 3, n is 0 or an integer of 1 to 7)
The present invention relates to a water-containing soft contact lens comprising a polymer obtained by polymerizing a polymerization component containing a fluorine-containing styrene derivative (A) and N, N-dimethyl (meth) acrylamide (B).

[0010]

BEST MODE FOR CARRYING OUT THE INVENTION As described above, the hydrous soft contact lens of the present invention has the general formula (I):

[0011]

Embedded image

(Wherein R ¹ is a hydrogen atom or a methyl group,
m is an integer of 1 to 3, n is 0 or an integer of 1 to 7)
And a polymer obtained by polymerizing a polymerization component containing the fluorine-containing styrene derivative (A) and N, N-dimethyl (meth) acrylamide (B).

The fluorine-containing styrene derivative (A) used in the present invention imparts excellent oxygen permeability which does not depend on the water content to the obtained water-containing soft contact lens, and the mechanical strength of the water-containing soft contact lens. It is a component to improve.

The fluorine-containing styrene derivative (A) is
It is a compound represented by the general formula (I). In the general formula (I), n is 0 or an integer of 1 to 7, but when n exceeds 7, purification is difficult and the fluorine-containing alkylene chain becomes too long. However, the mechanical strength of the obtained hydrous soft contact lens is lowered, which is not preferable. Note that n is preferably an integer of 1 to 5.

A typical example of the fluorine-containing styrene derivative (A) is 4-vinylbenzyl-2 ', 2.
′, 2′-Trifluoroethyl ether, 4-vinylbenzyl-3 ′, 3 ′, 3′-trifluoropropyl ether, 4-vinylbenzyl-4 ′, 4 ′, 4′-trifluorobutyl ether, 4-vinyl Benzyl-2 ', 2
′, 3 ′, 3 ′, 3′-pentafluoropropyl ether, 4-vinylbenzyl-2 ′, 2 ′, 3 ′, 3 ′, 4
′, 4 ′, 4′-heptafluorobutyl ether, 4-
Vinylbenzyl-3 ', 3', 4 ', 4', 5 ', 5
′, 6 ′, 6 ′, 6′-nonafluorohexyl ether, 4-vinylbenzyl-3 ′, 3 ′, 4 ′, 4 ′, 5
', 5', 6 ', 6', 7 ', 7', 8 ', 8', 9
', 9', 10 ', 10', 10'-heptadecafluorodecyl ether and the like can be mentioned, and these can be used alone or in combination of two or more kinds. Among these, 4-vinylbenzyl-3 ′, 3 ′, 4 ′, 4 from the viewpoint of great effect of improving oxygen permeability and mechanical strength of the obtained hydrous soft contact lens.
′, 5 ′, 5 ′, 6 ′, 6 ′, 6′-nonafluorohexyl ether is preferred.

The N, N-dimethyl (meth) acrylamide (B) used in the present invention imparts an appropriate water content to the obtained water-containing soft contact lens as a water-containing contact lens, and makes the water-containing soft contact lens flexible. Is a component that imparts.

The term "-(meth) acryl" as used herein means "-acryl" and / or "-methacryl".
Means

The weight ratio of the fluorine-containing styrene derivative (A) to N, N-dimethyl (meth) acrylamide (B) (fluorine-containing styrene derivative (A) / N, N-dimethyl (meth) acrylamide (B)). Is preferably adjusted to 10/90 or more, preferably 15/85 or more, in order to sufficiently exert the effect of improving the oxygen permeability and mechanical strength of the fluorine-containing styrene derivative (A). In addition, the weight ratio is such that the content of N, N-dimethyl (meth) acrylamide (B) is relatively small, and the water content and flexibility of the resulting water-containing soft contact lens may be reduced. In order to eliminate it, it is desirable to adjust it to 80/20 or less, preferably 75/25 or less.

The polymerization component used in the present invention contains the above-mentioned fluorine-containing styrene derivative (A) and N, N-dimethyl (meth) acrylamide (B). In the present invention, in addition to these, Also, a polymerizable monomer (C) copolymerizable with the fluorine-containing styrene derivative (A) and N, N-dimethyl (meth) acrylamide (B) is appropriately added depending on the properties of the intended water-containing soft contact lens. It can be added to the polymerization component.

For example, in order to impart hydrophilicity to the obtained water-containing soft contact lens or to improve the water content, a hydrophilic monomer can be used as the polymerizable monomer (C).

Representative examples of the hydrophilic monomer include, for example, hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, hydroxybutyl (meth) acrylate and dihydroxypropyl (meth).
Acrylate, dihydroxybutyl (meth) acrylate, diethylene glycol mono (meth) acrylate,
Hydroxyl group-containing (meth) acrylates such as triethylene glycol mono (meth) acrylate, propylene glycol mono (meth) acrylate, dipropylene glycol mono (meth) acrylate; (meth) acrylic acid; aminoethyl (meth) acrylate, N-methyl Aminoalkyl (meth) acrylates such as aminoethyl (meth) acrylate, N, N-dimethylaminoethyl (meth) acrylate, 2-butylaminoethyl (meth) acrylate; methoxyethyl (meth) acrylate, ethoxyethyl (meth) acrylate Alkoxy group-containing (meth) acrylates such as methoxydiethylene glycol (meth) acrylate; maleic anhydride; maleic acid; maleic acid derivatives; fumaric acid; fumaric acid derivatives; aminostyrene; Kishisuchiren and the like, they can be used alone or in admixture of two or more.

For example, in order to further improve the oxygen permeability and mechanical strength of the obtained hydrous soft contact lens, a silicon-containing monomer can be used as the polymerizable monomer (C).

Examples of the silicon-containing monomer include silicon-containing (meth) acrylate, silicon-containing styrene derivative, and silicon-containing fumarate.

Typical examples of the silicon-containing (meth) acrylate include, for example, trimethylsiloxydimethylsilylmethyl (meth) acrylate, trimethylsiloxydimethylsilylpropyl (meth) acrylate, methylbis (trimethylsiloxy) silylpropyl (meth).
Acrylate, tris (trimethylsiloxy) silylpropyl (meth) acrylate, mono [methylbis (trimethylsiloxy) siloxy] bis (trimethylsiloxy) silylpropyl (meth) acrylate, tris [methylbis (trimethylsiloxy) siloxy] silylpropyl (meth) acrylate , Methylbis (trimethylsiloxy) silylpropylglyceryl (meth) acrylate, tris (trimethylsiloxy) silylpropylglyceryl (meth) acrylate, mono [methylbis (trimethylsiloxy) siloxy] bis (trimethylsiloxy) silylpropylglyceryl (meth) acrylate,
Trimethylsilylethyl tetramethyldisiloxypropylglyceryl (meth) acrylate, trimethylsilylmethyl (meth) acrylate, trimethylsilylpropyl (meth) acrylate, trimethylsilylpropylglyceryl (meth) acrylate, trimethylsiloxydimethylsilylpropylglyceryl (meth) acrylate, methylbis (trimethylsiloxy) ) Silylethyltetramethyldisiloxymethyl (meth) acrylate, tetramethyltriisopropylcyclotetrasiloxanylpropyl (meth) acrylate, tetramethyltripropylcyclotetrasiloxybis (trimethylsiloxy)
Examples include silylpropyl (meth) acrylate.

Typical examples of the silicon-containing styrene derivative include, for example, the general formula (II):

[0026]

[Chemical 4]

(In the formula, p is an integer of 1 to 15, q is 0 or 1, and r is an integer of 1 to 15). When p or r in the general formula (II) is an integer of 16 or more, it becomes difficult to purify or synthesize the silicon-containing styrene derivative, and the hardness of the resulting water-containing soft contact lens decreases. When q is an integer of 2 or more, it tends to be difficult to synthesize the silicon-containing styrene derivative.

Typical examples of the silicon-containing styrene derivative represented by the above general formula (II) are, for example, tris (trimethylsiloxy) silylstyrene, bis (trimethylsiloxy) methylsilylstyrene, (trimethylsiloxy) dimethylsilylstyrene, tris ( Trimethylsiloxy) siloxydimethylsilylstyrene, [bis (trimethylsiloxy) methylsiloxy] dimethylsilylstyrene, heptamethyltrisiloxanylstyrene,
Nonamethyltetrasiloxanyl styrene, pentadecamethylheptasiloxanyl styrene, heneicosamethyl decasiloxanyl styrene, heptacosamethyl tridecasiloxanyl styrene, hentriacontamethylpentadecasiloxanyl styrene, trimethylsiloxy Pentamethyldisiloxymethylsilylstyrene, tris (pentamethyldisiloxy) silylstyrene, tris (trimethylsiloxy) siloxybis (trimethylsiloxy) silylstyrene, bis (heptamethyltrisiloxy) methylsilylstyrene, tris [methylbis (trimethylsiloxy) siloxy ] Silylstyrene, trimethylsiloxybis [tris (trimethylsiloxy) siloxy] silylstyrene, heptakis (trimethylsiloxy) trisiloxanylstyrene , Nonamethyltetrasiloxyundecylmethylpentasiloxymethylsilylstyrene, tris [tris (trimethylsiloxy) siloxy] silylstyrene, tris (trimethylsiloxyhexamethyl) tetrasiloxytris (trimethylsiloxy) siloxytrimethylsiloxysilylstyrene, nonakis (trimethylsiloxy) ) Tetrasiloxanylstyrene, bis (tridecamethylhexasiloxy) methylsilylstyrene and the like.

Representative examples of the silicon-containing styrene derivative other than the silicon-containing styrene derivative represented by the general formula (II) include, for example, heptamethylcyclotetrasiloxanylstyrene, heptamethylcyclotetrasiloxybis (trimethylsiloxy). Examples thereof include silylstyrene and tripropyltetramethylcyclotetrasiloxanylstyrene.

As the silicon-containing fumarate, a compound having a fluoroalkyl group and a silicon-containing alkyl group in the same molecule is preferable in order to enhance the oxygen permeability of the resulting water-containing soft contact lens.

As typical examples of the silicon-containing fumarate, for example, trifluoroethyl (trimethylsilylmethyl) fumarate, trifluoroethyl (trimethylsilylpropyl) fumarate, hexafluoroisopropyl (trimethylsilylmethyl) fumarate, hexafluoroisopropyl (trimethylsilylpropyl) fumarate, Octafluoropentyl (trimethylsilylmethyl) fumarate, octafluoropentyl (trimethylsilylpropyl) fumarate, trifluoroethyl (pentamethyldisiloxanylmethyl) fumarate, trifluoroethyl (pentamethyldisiloxanylpropyl) fumarate, hexafluoroisopropyl ( Pentamethyldisiloxanylmethyl) fumarate, hexafluoroisopropyl ( Ntamethyldisiloxanylpropyl) fumarate, octafluoropentyl (pentamethyldisiloxanylmethyl) fumarate, octafluoropentyl (pentamethyldisiloxanylpropyl) fumarate, trifluoroethyl (tetramethyl (trimethylsiloxy) disiloxy) Sanylmethyl) fumarate, trifluoroethyl (tetramethyl (trimethylsiloxy)
Disiloxanylpropyl) fumarate, hexafluoroisopropyl (tetramethyl (trimethylsiloxy) disiloxanylmethyl) fumarate, hexafluoroisopropyl (tetramethyl (trimethylsiloxy) disiloxanylpropyl) fumarate, octafluoropentyl (tetramethyl (Trimethylsiloxy) disiloxanylmethyl) fumarate, octafluoropentyl (tetramethyl (trimethylsiloxy) disiloxanylpropyl) fumarate, trifluoroethyl (tris (trimethylsiloxy) silylmethyl) fumarate, trifluoroethyl (tris (trimethyl Siloxy) silylpropyl) fumarate, hexafluoroisopropyl (tris (trimethylsiloxy) silylmethyl) fumarate, hexafluoroiso Propyl (tris (trimethylsiloxy) silyl propyl) fumarate, octafluoropentyl (tris (trimethylsiloxy) silylmethyl) fumarate, octafluoropentyl (tris (trimethylsiloxy) silyl propyl) such as fumarate and the like.

These silicon-containing monomers can be used alone or in admixture of two or more. Also,
Among such silicon-containing monomers, tris (trimethylsiloxy) silylpropyl (meth) acrylate is used because it is possible to easily obtain a hydrous soft contact lens having good mechanical strength without lowering oxygen permeability. Silicon-containing (meth) acrylates typified and silicon-containing styrene derivatives typified by tris (trimethylsiloxy) silylstyrene are preferably used.

For example, when the hardness of the obtained hydrous soft contact lens is adjusted to impart hardness or softness, or further improve flexibility,
A reinforcing monomer can be used as the polymerizable monomer (C).

Typical examples of the reinforcing monomer include, for example, methyl (meth) acrylate, ethyl (meth) acrylate, isopropyl (meth) acrylate, n-propyl (meth) acrylate, isobutyl (meth) acrylate, n-butyl (meth). ) Acrylate, t-butyl (meth) acrylate, n-pentyl (meth) acrylate, t-pentyl (meth) acrylate, hexyl (meth) acrylate, heptyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, n-octyl (Meth) acrylate, n-decyl (meth) acrylate, n-dodecyl (meth) acrylate, nonyl (meth) acrylate, stearyl (meth) acrylate, cyclopentyl (meth) acrylate, cyclohexyl (meth) acrylate Straight-chain, branched-chain or cyclic alkyl (meth) acrylates such as ether; 2-ethoxyethyl (meth) acrylate, 3-ethoxypropyl (meth) acrylate, 2-methoxyethyl (meth) acrylate, 3-methoxy Alkoxyalkyl (meth) acrylates such as propyl (meth) acrylate; Alkylthioalkyl (meth) acrylates such as ethylthioethyl (meth) acrylate and methylthioethyl (meth) acrylate; styrene; α-methylstyrene; methylstyrene, ethylstyrene, Alkyl styrenes such as propyl styrene, n-butyl styrene, t-butyl styrene, isobutyl styrene, pentyl styrene; methyl-α-methyl styrene, ethyl-α-methyl styrene, propyl-α-methyl styrene, n- Butyl-α-methylstyrene, t-butyl-α-methylstyrene, isobutyl-α-methylstyrene, pentyl-α-
Examples thereof include alkyl-α-methylstyrene such as methylstyrene, which may be used alone or in admixture of two or more.

Further, for example, in order to impart anti-lipid stain property to the obtained hydrous soft contact lens, for example, fluoroalkyl (meth) acrylate, fluoroalkylstyrene or the like is used as the polymerizable monomer (C). be able to.

Typical examples of the fluoroalkyl (meth) acrylate are, for example, 2,2,2-trifluoroethyl (meth) acrylate, 2,2,3,3-tetrafluoropropyl (meth) acrylate and 2,2. ，
3,3-Tetrafluoro-t-pentyl (meth) acrylate, 2,2,3,4,4,4-hexafluorobutyl (meth) acrylate, 2,2,3,4,4,4-hexafluoro- t-hexyl (meth) acrylate,
2,3,4,5,5,5-hexafluoro-2,4-bis (trifluoromethyl) pentyl (meth) acrylate, 2,2,3,3,4,4-hexafluorobutyl (meth) acrylate , 2, 2, 2, 2 ', 2', 2 '
-Hexafluoroisopropyl (meth) acrylate,
2,2,3,3,4,4,4-heptafluorobutyl (meth) acrylate, 2,2,3,3,4,4,5
5-octafluoropentyl (meth) acrylate,
2,2,3,3,4,4,5,5,5-nonafluoropentyl (meth) acrylate, 2,2,3,3,4
4,5,5,6,6,7,7-dodecafluoroheptyl (meth) acrylate, 3,3,4,4,5,5,6
6,7,7,8,8-dodecafluorooctyl (meth)
Acrylate, 3,3,4,4,5,5,6,6,7,
7,8,8,8-Tridecafluorooctyl (meth) acrylate, 2,2,3,3,4,4,5,5,6
6,7,7,7-tridecafluoroheptyl (meth) acrylate, 3,3,4,4,5,5,6,6,7,
7,8,8,9,9,10,10-hexadecafluorodecyl (meth) acrylate, 3,3,4,4,5,
5,6,6,7,7,8,8,9,9,10,10,1
0-heptadecafluorodecyl (meth) acrylate,
3,3,4,4,5,5,6,6,7,7,8,8,
9,9,10,10,11,11-octadecafluoroundecyl (meth) acrylate, 3,3,4,4
5,5,6,6,7,7,8,8,9,9,10,1
0,11,11,11-nonadecafluoroundecyl (meth) acrylate, 3,3,4,4,5,5,6
6,7,7,8,8,9,9,10,10,11,1
Examples include 1,12,12-eicosafluorododecyl (meth) acrylate.

Typical examples of the fluoroalkylstyrene include p-trifluoromethylstyrene and p-trifluoromethylstyrene.
-Heptafluoropropyl styrene, p-pentafluoroethyl styrene and the like.

The fluoroalkyl (meth) acrylate and fluoroalkyl styrene may be used alone or in combination with 2
A mixture of two or more species can be used.

The amount of the polymerizable monomer (C) blended varies depending on the type of the monomer and cannot be determined unconditionally, but the fluorine-containing styrene derivative (A) and N, N-dimethyl ( In order to reduce the amount of (meth) acrylamide (B) compounded and to prevent the oxygen-permeable, mechanical strength and flexibility improving effects of the resulting hydrous soft contact lens from being sufficiently expressed,
The amount of the polymerizable monomer (C) blended is 5
It is desirable to adjust the content to be 0% by weight or less, preferably 45% by weight or less. Further, in order to eliminate the possibility that the effect of using the polymerizable monomer (C) is not sufficiently exhibited, the amount of the polymerizable monomer (C) to be blended is 1% by weight or more, preferably 5% by weight of the polymerization component. weight%
It is desirable to make adjustments as described above.

Further, in the present invention, in order to further improve the mechanical strength and impart durability to the obtained hydrous soft contact lens, it is preferable to appropriately add a crosslinking monomer to the polymerization component.

Typical examples of the crosslinkable monomer include ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, dipropylene glycol di. (Meth) acrylate, diallyl fumarate, allyl (meth) acrylate, vinyl (meth) acrylate, trimethylolpropane tri (meth) acrylate, methacryloyloxyethyl (meth) acrylate, divinylbenzene, diallyl phthalate, diallyl adipate, triallyl Diisocyanate, N-vinylmethylenepyrrolidone, 4-vinylbenzyl (meth) acrylate, 3-vinylbenzyl (meth) acrylate,
2,2-bis ((meth) acryloyloxyphenyl)
Hexafluoropropane, 2,2-bis ((meth) acryloyloxyphenyl) propane, 1,4-bis (2
-(Meth) acryloyloxyhexafluoroisopropyl) benzene, 1,3-bis (2- (meth) acryloyloxyhexafluoroisopropyl) benzene,
1,2-bis (2- (meth) acryloyloxyhexafluoroisopropyl) benzene, 1,4-bis (2-
(Meth) acryloyloxyisopropyl) benzene,
1,3-bis (2- (meth) acryloyloxyisopropyl) benzene, 1,2-bis (2- (meth) acryloyloxyisopropyl) benzene and the like,
These may be used alone or in combination of two or more. Among these, ethylene glycol di (meth) acrylate and vinylbenzyl (meth) acrylate are preferable from the viewpoint of having a large effect of improving the mechanical strength and durability of the hydrous soft contact lens obtained.

The amount of the crosslinkable monomer to be blended is 0.1 with respect to 100 parts by weight (parts by weight, the same applies hereinafter) of the total amount of the polymerization components in order to sufficiently exert the effects of improving mechanical strength and imparting durability. It is desirable to adjust the amount to be 01 parts or more, preferably 0.05 parts or more. Further, in order to eliminate the possibility that the obtained hydrous soft contact lens becomes brittle, the amount of the crosslinkable monomer to be blended is adjusted to 5 parts or less, preferably 1 part or less, relative to 100 parts of the total amount of the polymerization components. It is desirable to do.

Further, in the present invention, a polymerizable ultraviolet absorber, a polymerizable ultraviolet absorbing dye or the like can be used as a polymerization component in order to impart ultraviolet absorbing ability to the hydrous soft contact lens.

As a typical example of the above-mentioned polymerizable ultraviolet absorber, a benzophenone-based polymerizable ultraviolet absorber such as 2-hydroxy-4- (meth) acryloyloxybenzophenone, 2- (2'-hydroxy-5 '-( Examples thereof include benzotriazole-based polymerizable ultraviolet absorbers such as (meth) acryloyloxyethoxy-3′-t-butylphenyl) -5-methyl-2H-benzotriazole, which may be used alone or in admixture of two or more. Can be used.

If the amount of the polymerizable ultraviolet absorber blended is too large, physical properties such as mechanical strength of the obtained hydrous soft contact lens tend to be deteriorated. It is desirable that the amount is 3 parts or less, preferably 0.1 to 2 parts, relative to 100 parts of the total amount of the components.

Typical examples of the above-mentioned polymerizable ultraviolet absorbing dyes include 2,4-dihydroxy-3 (p-styrenoazo) benzophenone and 2,4-dihydroxy-5-.
(P-Styrenoazo) benzophenone, 2,4-dihydroxy-3- (p- (meth) acryloyloxymethylphenylazo) benzophenone, 2,4-dihydroxy-5- (p- (meth) acryloyloxymethylphenylazo) benzophenone Examples thereof include benzophenone-based polymerizable ultraviolet absorbing dyes and benzoic acid-based polymerizable ultraviolet absorbing dyes such as phenyl 2-hydroxy-4- (p-styrenoazo) benzoate. These can be used alone or in admixture of two or more. Can be used.

If the amount of the polymerizable ultraviolet absorbing dye is too large, the resulting hydrous soft contact lens has poor physical properties such as mechanical strength, and the hydrous soft contact lens has a dark color. Since the transparency of the water-containing soft contact lens tends to be less likely to pass through the visible light, the content of such a compounding agent is 3 parts or less, preferably 0.1 part or less based on 100 parts of the total amount of the polymerization components. It is desirable that it is 2 parts.

A polymerizable dye or the like can be used as a polymerization component for coloring the obtained hydrous soft contact lens.

Typical examples of the polymerizable dyes include 1-phenylazo-4- (meth) acryloyloxynaphthalene and 1-phenylazo-2-hydroxy-3-.
(Meth) acryloyloxynaphthalene, 1-naphthylazo-2-hydroxy-3- (meth) acryloyloxynaphthalene, 1- (α-anthrylazo) -2-hydroxy-3- (meth) acryloyloxynaphthalene,
1-((4 '-(phenylazo) phenyl) azo) -2
-Hydroxy-3- (meth) acryloyloxynaphthalene and other azo-based polymerizable dyes; 1,5-bis ((meth)
Acryloylamino) -9,10-anthraquinone, 1
Anthraquinone-based polymerizable dyes such as-(4'-vinylbenzoylamide) -9,10-anthraquinone and 4-amino-1- (4'-vinylbenzoylamide) -9,10-anthraquinone; o-nitroanilinomethyl Nitro polymerizable dyes such as (meth) acrylate; (meth)
Examples thereof include phthalocyanine-based polymerizable dyes such as acryloylated tetraaminocopper phthalocyanine and (meth) acryloylated (dodecanoylated tetraaminocopper phthalocyanine), and these can be used alone or in admixture of two or more.

If the amount of the polymerizable dye is too large, the resulting hydrous soft contact lens has poor physical properties such as mechanical strength, and the hydrous soft contact lens is too dark in color. As a result, the transparency of the water-containing soft contact lens tends to be less likely to pass through visible light, and therefore the amount of such a compound is 1 part or less, preferably 0.0
It is desirable that the amount is 01 to 0.5 part.

Polymerization components such as the fluorine-containing styrene derivative (A) and N, N-dimethyl (meth) acrylamide (B) are used for polymerization after adjusting the compounding amounts thereof appropriately.

That is, in the present invention, the fluorine-containing styrene derivative (A) and N, N-dimethyl (meth) acrylamide, and optionally the polymerizable monomer (C),
A polymer can be obtained by adjusting a desired amount of a polymerization component such as a crosslinkable monomer within the range of the above-mentioned compounding amount, and adding a radical polymerization initiator to this, and polymerizing by a usual method.

The above-mentioned usual method means, for example, mixing a radical polymerization initiator and then gradually heating it in the temperature range of room temperature to about 130 ° C. (thermal polymerization), microwave, ultraviolet ray,
This is a method of polymerizing by irradiating an electromagnetic wave such as radiation (γ ray). When performing thermal polymerization, the temperature may be raised stepwise. The polymerization may be performed by a bulk polymerization method, a solution polymerization method using a solvent or the like, or another method.

Representative examples of the radical polymerization initiator include, for example, azobisisobutyronitrile, azobisdimethylvaleronitrile, benzoyl peroxide, and t.
-Butyl hydroperoxide, cumene hydroperoxide and the like can be mentioned, and these can be used alone or in admixture of two or more kinds. When the polymerization is carried out by using light rays or the like, it is preferable to further add a photopolymerization initiator or a sensitizer. The amount of the polymerization initiator or sensitizer added is 0.0 with respect to 100 parts of the total amount of the polymerization components.
It is desirable that the amount is 02 to 2 parts, preferably 0.01 to 1 part.

In the present invention, as a method for molding a soft contact lens, a molding method usually practiced by those skilled in the art can be adopted. Examples of such a molding method include a cutting method and a mold method. The cutting method is to perform polymerization in an appropriate mold or container, obtain a rod-shaped, block-shaped, or plate-shaped material (polymer), and then machine it into the desired shape by mechanical processing such as cutting or polishing. , A method of obtaining a molded product. The mold method is a method of obtaining a molded product by polymerizing the above-mentioned polymerization components in a mold corresponding to the shape of a desired contact lens to obtain a molded product, and mechanically finishing it if necessary. .

In addition to these methods, for example, the lens material (polymer) is impregnated with a monomer that gives a hard polymer, and then the monomer is polymerized to further harden the whole body, followed by cutting, A method of removing a hard polymer from a molded product processed into the above shape to obtain a molded product made of a lens material (Japanese Patent Laid-Open No. 62-2780241, Japanese Patent Laid-Open No. 11-11854) and the like can also be applied in the present invention. it can.

Then, the molded article obtained as described above is hydrated by immersing it in distilled water, physiological saline, an aqueous solution whose osmotic pressure and pH are appropriately adjusted, and hydrated soft contact. It can be a lens.

The hydrous soft contact lens of the present invention has excellent oxygen permeability, good mechanical strength and flexibility without depending on the water content, and further adjusts the compounding ratio of each polymerization component. By doing so, the water content, the mechanical strength and the flexibility can be arbitrarily adjusted, and a contact lens can be obtained according to the purpose.

[0059]

EXAMPLES Next, the hydrous soft contact lens of the present invention will be described in more detail based on examples, but the present invention is not limited to these examples.

Example 1 4-Vinylbenzyl-3 ', 3', 4 as a polymerization component
A mixture of 40 parts of ', 4', 5 ', 5', 6 ', 6', 6'-nonafluorohexyl ether, 60 parts of N, N-dimethylacrylamide and 0.3 parts of ethylene glycol dimethacrylate is used, Total amount of polymerization component 100
Then, 0.1 part of 2,2′-azobis (2,4-dimethylvaleronitrile) as a polymerization initiator was added to and dissolved therein, and the mixture was poured into a glass test tube having an inner diameter of 14 mm.

Next, the test tube was transferred into a circulation type constant temperature water tank, and was heated at 30 ° C. for 24 hours, 40 ° C. for 16 hours, and 50 ° C.
After heating for 8 hours, the film was transferred to a circulation dryer. Then, keep at 50 ° C. for 5 hours in the circulating dryer, and
Increase the temperature to 120 ° C at a rate of 10 ° C for 5 hours, and
The polymerization was carried out while maintaining the time. After that, it was gradually cooled to room temperature to obtain a rod-shaped polymer.

The obtained polymer was subjected to cutting and polishing to prepare a test piece having a desired thickness and a diameter of about 12 mm, and its physical properties were examined according to the following methods. Table 1 shows the results.

(A) Punching strength (i) Punching load Using a punching strength tester, a diameter of 1/16 was applied to the center of the test piece.
A push-in needle of inch was applied, and the punch-out load (g) at break of the test piece was measured. However, the values in Table 1 are values when the thickness of the test piece is converted to 0.2 mm.

(Ii) Elongation rate During the measurement of the (i) punch-out load, the elongation rate (%) at break of the test piece was measured.

(B) Rubber hardness A test piece having a thickness of 4 mm and smooth on both sides was immersed in distilled water for 2 weeks for hydration treatment, and then JIS K 6301 was used.
Spring-type hardness test (A)
The rubber hardness (no unit) at 25 ° C. was measured according to the mold.

(C) Water content Water content (% by weight) of a test piece having a thickness of 1 mm at 35 ° C.
Was calculated based on the following equation.

Moisture content (% by weight) = {(W−Wo) / W} × 100 where W is the weight (g) of the test piece in the equilibrium water content after hydration treatment, and Wo is the value after hydration treatment. The weight (g) of a test piece in a dry state dried in a dryer is shown.

(D) Oxygen permeability coefficient (i) Measured value Using a Seikaken film oxygen permeability meter manufactured by Rika Seiki Kogyo Co., Ltd., a test piece having a thickness of 0.2 mm was prepared in physiological saline at 35 ° C. The oxygen permeability coefficient was measured. The unit of oxygen permeability coefficient is (cm ² / sec) · (mlO ₂ / (ml · mmH
g)), and the oxygen permeation coefficient shown in Table 1 is a value obtained by multiplying the original value by 10 ¹¹ .

(Ii) Calculated value It was calculated based on the formula described in the journal of Fatt et al .: Dk = 2.0E-11exp (0.0411 × water content (% by weight)).

Examples 2 to 16 and Comparative Examples 1 to 2 Polymerization was carried out in the same manner as in Example 1 except that the composition of the polymerization components was changed as shown in Table 1.
A test piece was prepared from the obtained polymer.

The physical properties of the obtained test piece were examined in the same manner as in Example 1. Table 1 shows the results.

The abbreviations in Table 1 indicate the following monomers.

FSt: 4-vinylbenzyl-3 ',
3 ', 4', 4 ', 5', 5 ', 6', 6 ', 6'-nonafluorohexyl ether DMAA: N, N-dimethylacrylamide MMA: methyl methacrylate 6FP: 2,2,2,2' , 2 ', 2'-hexafluoroisopropyl methacrylate Si4MA: tris (trimethylsiloxy) silylpropyl methacrylate SiSt: tris (trimethylsiloxy) silylstyrene N-VP: N-vinyl-2-pyrrolidone EDMA: ethylene glycol dimethacrylate VBMA: vinyl Benzyl methacrylate

[0074]

[Table 1]

From the results shown in Table 1, the measured values of the oxygen permeability coefficient of the polymers obtained in Examples 1 to 16 having various water contents were compared with the calculated values obtained based on the water contents. It can be seen that all are significantly larger. That is, it can be seen that the polymers obtained in Examples 1 to 16 all have excellent oxygen permeability without depending on the water content.

On the other hand, the measured value of the oxygen permeability coefficient of the polymer obtained in Comparative Example 1 is smaller than the calculated value obtained based on the water content, and the polymer obtained in Comparative Example 2 is The measured and calculated values of the oxygen permeability coefficient of are almost the same. That is, it can be seen that the oxygen permeability of the polymers obtained in Comparative Examples 1 and 2 depended on the water content.

Further, the polymers obtained in Examples 1 to 16 have good mechanical strength, rubber hardness of less than 70, good flexibility, and a blending ratio of polymerization components. It is understood that the water content, the mechanical strength and the flexibility can be arbitrarily adjusted by appropriately adjusting.

[0078]

The hydrous soft contact lens of the present invention has excellent oxygen permeability, good mechanical strength and flexibility without depending on the water content, and further adjusts the blending ratio of the polymerization component. As a result, the water content, the mechanical strength and the flexibility can be adjusted as desired, so that the contact lens can be produced according to the purpose.

(72) Inventor Noriko Iwata Noriko Iwata 5-10 Takamoridai, Kasugai City, Aichi Prefecture Menicon Co., Ltd. Silicone Electronic Materials Research Laboratory (72) Inventor Yasuo Tarumi 1 Hitomi, Osamu Matsuida-cho, Usui-gun, Gunma Shin-Etsu Chemical Co., Ltd.

Claims (7)

[Claims] 1. A compound represented by the general formula (I): (In the formula, R ¹ is a hydrogen atom or a methyl group, m is an integer of 1 to 3, n is an integer of 0 or 1 to 7) and a fluorine-containing styrene derivative (A) and N, N-dimethyl ( A hydrous soft contact lens made of a polymer obtained by polymerizing a polymerization component containing (meth) acrylamide (B). 2. A fluorine-containing styrene derivative (A) and N,
The weight ratio with N-dimethyl (meth) acrylamide (B) (fluorine-containing styrene derivative (A) / N, N-dimethyl (meth) acrylamide (B)) is 10/90 to 80 /.
20. The hydrous soft contact lens according to claim 1, which is 20. 3. The polymerization component according to claim 1, which contains a fluorine-containing styrene derivative (A) and a polymerizable monomer (C) copolymerizable with N, N-dimethyl (meth) acrylamide (B). Hydrous soft contact lens. 4. The hydrous soft contact lens according to claim 3, wherein the polymerizable monomer (C) is a silicon-containing (meth) acrylate or a silicon-containing styrene derivative. 5. The hydrous soft contact lens according to claim 3, wherein the amount of the polymerizable monomer (C) blended is 50% by weight or less based on the weight of the polymerization component. 6. The hydrous soft contact lens according to claim 1, wherein the polymerization component contains a crosslinkable monomer. 7. The hydrous soft contact lens according to claim 6, wherein the compounding amount of the crosslinkable monomer is 0.01 to 5 parts by weight based on 100 parts by weight of the total amount of the polymerization components.