JPH0117128B2 - - Google Patents

Description

[Detailed description of the invention]

[Industrial Application Field] The present invention relates to contact lens materials, and in particular to contact lens materials that have excellent oxygen permeability and hydrophilicity, can be worn continuously for long periods of time, are substantially water-free, and are easy to handle. It concerns the material of the lens. [Prior art and its problems] Conventionally, for example, contact lenses containing polymethyl methacrylate as a main component have been put to practical use. Although polymethyl methacrylate, the main component of contact lenses, has great advantages such as excellent optical properties and durability,
Due to its poor oxygen permeability, it has a major drawback in that it cannot be worn continuously for long periods of time due to corneal physiology. Therefore, as a solution to the above-mentioned drawbacks of hard type contact lenses, water-containing contact lenses containing poly-2-hydroxyethyl methacrylate as a main component have been put into practical use, and soft type contact lenses such as these have been put into practical use. Although the lenses are comfortable to wear to some extent due to their good hydrophilic properties, their oxygen permeability is not sufficient.
Therefore, they cannot be worn continuously for long periods of time, and because they are water-containing, they are more difficult to handle than hard contact lenses. In addition, in order to enable continuous wear, contact lenses with high water content, for example, containing N-vinylpyrrolidone as a main component, have been proposed, and although these have favorable features in terms of hydrophilicity and oxygen permeability, However, due to its high water content, it has extremely poor mechanical strength, poor durability, and is extremely troublesome to handle. And the above polymethyl methacrylate, poly 2-hydroxyethyl methacrylate or poly N
-Contact lenses made of silicone rubber or silicone resin have been proposed as contact lenses that go beyond vinylpyrrolidone-based contact lenses, but these materials are not hydrophilic and require surface treatment to make them hydrophilic. Not only that, but the durability of the surface-treated hydrophilic membrane is poor and is not fully satisfactory. [Disclosure of the Invention] The present inventor has disclosed that the general formula [] (However, X ₁ to _{X 6} are selected from the group consisting of C ₁ to _{C 5} alkyl groups, aromatic groups, and Y groups, and Y group is (However, at least two or more of X ₁ to X ₆ are Y groups), R ₂ is CH ₃ or H, R ₁ ,
R ₁ ″ is a C ₁ to C ₅ alkyl group, an aromatic group, and Z
The Z group is selected from the group consisting of

[Formula], R ₁ ′ does not represent a group but represents a bonded chain of R ₁ ′-O-R ₁ ′, or a group consisting of a C ₁ to C ₅ alkyl group, an aromatic group, and a Z group selected from l, m,
k, l', m', k' are integers from 0 to 10, and n is from 1 to
An integer of 10, j is 0 or 1. ), an ester consisting of an organosiloxane represented by the above, a _C1 to _C10 monohydric or polyhydric alcohol, and an acid selected from the group consisting of methacrylic acid, acrylic acid, and itaconic acid, and/or 1 to 20 fluorine atoms. A material made of a copolymer copolymerized using at least an ester consisting of a linear or branched fluoroalkyl alcohol having atoms and an acid selected from the group consisting of methacrylic acid, acrylic acid, and itaconic acid, Excellent permeability and hydrophilicity,
Moreover, it is virtually non-hydrous, and contact lenses made of such materials are easy to handle, have excellent durability, are comfortable to wear, and can be worn continuously for long periods of time. They discovered that it has excellent effectiveness and dimensional stability. In addition, as the organosiloxane represented by the above general formula [1], for example, 1,3-bis(methacryloxyethoxypropyl)-1,1,3,3-(tetramethyl)disiloxane, 1,5-bis(acryloxyethoxypropyl)-1,1,3,3,5,5-(hexamethyl)
Trisiloxane 1,7-bis(methacryloxyethoxypropyl)-1,1,7,7-tetrakis(trimethylsiloxy)-3,3,5,5-(tetramethyl)-
Tetrasiloxane 1,3-bis(methacryloxyethoxypropyl)-1,1,3,3-tetrakis(bis(trimethylsiloxy)methylsiloxy)disiloxane, 1,3-bis(acryloxyethoxypropyl)-1,1,3,3-(tetraphenyl)disiloxane, 1,5-bis(methacryloxyethoxypropyl)-1,3,5-(trimethyl)-1,3,5-
(tripropyl)trisiloxane, 1,5-bis(methacryloxyethoxypropyl)-1,3,5,7-(tetramethyl)-3,7
-(dipropyl)cyclotetrasiloxane, 1,3,5-tris(acryloxyethoxypropyl)-1,3,5,7-(tetramethyl)-7
-(propyl)cyclotetrasiloxane, 1,3,5,7-tetrakis(methacryloxyethoxypropyl)-1,3,5,7-(tetramethyl)cyclotetrasiloxane, Examples include [tris(acryloxyethoxypropyl)dimethylsiloxy]-methylsilane. In addition, examples of esters consisting of a _C1 to _C10 monohydric or polyhydric alcohol and an acid selected from the group consisting of methacrylic acid, acrylic acid, and itaconic acid include methyl methacrylate, methyl acrylate,
Dimethyl itaconate, monomethyl itaconate, ethyl methacrylate, ethyl acrylate, diethyl itaconate, monoethyl itaconate, n-propyl methacrylate, n-propyl acrylate, di-n-propyl itaconate, mono-n-propyl itaconate, isopropyl methacrylate, isopropyl Acrylate, diisopropyl itaconate, monoisopropyl itaconate, n-butyl methacrylate, n-butyl acrylate, di-n-butyl itaconate, mono-n-butyl itaconate, pentyl methacrylate, pentyl acrylate, dipentyl itaconate, monopentyl itaconate, Neopentyl methacrylate, neopentyl acrylate, dineopentyl itaconate,
Mononeopentyl itaconate, n-hexyl methacrylate, n-hexyl acrylate, di-n-hexyl itaconate, mono-n-hexyl itaconate, cyclohexyl methacrylate, cyclohexyl acrylate, dicyclohexyl itaconate, monocyclohexyl itaconate, 2-ethylhexyl methacrylate, 2-ethylhexyl acrylate, di-2-ethylhexyl itaconate,
Mono-2-ethylhexyl itaconate, ethylene glycol dimethacrylate, ethylene glycol diacrylate, diethylene glycol dimethacrylate, diethylene glycol diacrylate, triethylene glycol dimethacrylate,
Triethylene glycol diacrylate, tetraethylene glycol dimethacrylate, tetraethylene glycol diacrylate, 1,3-butanediol dimethacrylate, 1,3-butanediol diacrylate, 1,4-butanediol dimethacrylate, 1,4-butane Diol diacrylate, 1,6-hexanediol dimethacrylate, 1,6-hexanediol diacrylate, neopentyl glycol dimethacrylate, neopentyl glycol diacrylate, trimethylolpropane trimethacrylate, trimethylolpropane triacrylate, pentaerythritol tetramethacrylate , pentaerythritol tetraacrylate, ethylene glycol monomethacrylate, ethylene glycol monoacrylate, diethylene glycol monomethacrylate, diethylene glycol monoacrylate, triethylene glycol monomethacrylate, triethylene glycol monoacrylate,
Examples include 2-hydroxypropyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxybutyl methacrylate, 2-hydroxybutyl acrylate, 2-hydroxystyrene methacrylate, and 2-hydroxystyrene acrylate. Among these, esters of monohydric alcohol and methacrylic acid or acrylic acid, or diesters of monohydric alcohol and itaconic acid are mainly used to improve the processability and toughness of polymer materials, and Monoesters of polyhydric alcohol and methacrylic acid or acrylic acid, or 1
Monoesters of alcohol and itaconic acid are mainly used to improve the hydrophilicity of polymer materials. It is also possible to use methacrylic acid, acrylic acid, acrylamide, methacrylamide, N-methylolmethacrylamide, N-vinylpyrrolidone, etc. in place of the above-mentioned esters used to improve hydrophilicity. Further, examples of esters consisting of a linear or branched fluoroalkyl alcohol having 1 to 20 fluorine atoms and an acid selected from the group consisting of methacrylic acid, acrylic acid, and itaconic acid include, for example, 2,2 , 2-trifluoroethyl methacrylate, 2,2,2-trifluoroethyl acrylate, bis-2,2,2-trifluoroethyl itaconate, 2,2,2-trifluoroethyl itaconate, 2,2,3 , 3-tetrafluoropropyl methacrylate, 2,2,3,3-tetrafluoropropyl acrylate, bis-2,2,
3,3-tetrafluoropropyl itaconate,
2,2,3,3-tetrafluoropropyl itaconate, 2,2,3,3,4,4,5,5-octafluoropentyl methacrylate, 2,2,
3,3,4,4,5,5-octafluoropentyl methacrylate, bis-2,2,3,3,4,
4,5,5-octafluoropentyl itaconate, 2,2,3,3,4,4,5,5-octafluoropentyl itaconate, 1H, 1H, 2H,
2H-heptadecafluorodecyl methacrylate,
1H, 1H, 2H, 2H-heptadecafluorodecyl acrylate, bis-1H, 1H, 2H, 2H-heptadecafluorodecyl itaconate, 1H, 1H,
2H,2H-heptadecafluorooctyl itaconate, 1H,1H-pentadecafluorooctyl methacrylate, 1H,1H-pentadecafluorooctyl acrylate, 1H,1H-pentadecafluorooctyl itaconate, bis-1H,1H-pentadeca Fluorooctyl itaconate, 1H, 1H
-pentafluoropropyl methacrylate, 1H,
1H-pentafluoropropyl acrylate, bis-1H, 1H-pentafluoropropyl itaconate, 1H, 1H-pentafluoropropyl itaconate, hexafluoroisopropyl methacrylate, hexafluoroisopropyl acrylate, bis-1H, 1H-pentafluoropropyl itaconate, hexafluoroisopropyl itaconate Nate,
Examples include 1H,1H-heptafluorobutyl methacrylate, 1H,1H-heptafluorobutyl acrylate, and bis-1H,1H-heptafluorobutyl itaconate. These esters mainly act together with the organosiloxane to improve the oxygen permeability of the polymer material, and also improve the optical transparency. In addition, a part of the organosiloxane may be represented by the general formula [2] (However, A ₃ is a C ₁ to C ₆ alkyl group, an aromatic group,
selected from the group consisting of B groups, where B groups are

[Formula], A ₂ and A ₂ ' are selected from the group consisting of C ₁ to C ₆ alkyl groups and aromatic groups, and n is 1
is an integer of ~3, m is a number of 0 or 1,
A ₅ is CH ₃ or H, A ₁ and A ₄ do not represent a group but represent a bonding chain connecting A ₁ - A ₄ , or A ₁ is C ₁ to C ₆
selected from the group consisting of alkyl groups, aromatic groups,
A ₄ is selected from the group consisting of a C ₁ to C ₆ alkyl group, an aromatic group, and a B group. ) may be copolymerized instead of the monofunctional organosiloxane. The organosiloxane represented by the above general formula [2] includes, for example, methacryloxyethoxypropylpentamethyldisiloxane, acryloxyethoxypropylpentamethyldisiloxane, methacryloxyethoxypropylheptamethyltrisiloxane, acryloxyethoxypropylheptamethyl Trisiloxane, methacryloxyethoxypropyltris (trimethylsiloxy)
Silane, acryloxyethoxypropyltris(trimethylsiloxy)silane, methacryloxyethoxypropylphenyltetramethyldisiloxane, acryloxyethoxypropylphenyltetramethyldisiloxane, methacryloxyethoxypropyltribenzyldiethyldisiloxane,
acryloxyethoxypropyltribenzyldiethyldisiloxane, methacryloxyethoxypropyl n-pentylhexamethyltrisiloxane,
Acryloxyethoxypropyl n-pentylhexamethyltrisiloxane, methacryloxyethoxypropyl di-n-propylpentamethyltrisiloxane, acryloxyethoxypropyl di-n-propylpentamethyltrisiloxane, methacryloxyethoxypropyl phenyl octamethyltetrasiloxane, acrylic Roxyethoxypropyl phenyl octamethyltetrasiloxane, methacryloxyethoxypropylisobutyltetramethyldisiloxane, acryloxyethoxypropylisobutyltetramethyldisiloxane, methacryloxyethoxypropylmethylbis(trimethylsiloxy)silane, acryloxyethoxypropylmethylbis(trimethyl) silane, methacryloxyethoxypropyltris(dimethylcyclohexylsiloxy)silane, acryloxyethoxypropyltris(dimethylcyclohexylsiloxy)silane, methacryloxyethoxypropylpentamethyldisiloxybis(trimethylsiloxy)silane, acryloxyethoxypropylpentamethylsilane siloxybis(trimethylsiloxy)silane, methacryloxyethoxypropylheptamethylcyclotetrasiloxane, acryloxyethoxypropylheptamethylcyclotetrasiloxane, methacryloxyethoxypropyltetramethyltripropylcyclotetrasiloxane,
Examples include acryloxyethoxypropyltetramethyltripropylcyclotetrasiloxane. The ratio of the organosiloxane and ester constituting the copolymer as a material for contact lenses is preferably about 95 to 20 parts by weight to about 5 to 80 parts by weight, and even more preferably. About 5 to 95 parts by weight of an ester of a monohydric alcohol and methacrylic acid or acrylic acid or a diester of a monohydric alcohol and itaconic acid is added to 5 to 80 parts by weight of the organosiloxane represented by the general formula [1].
Parts by weight, 50 parts by weight or less of esters of fluoroalkyl alcohol and methacrylic acid, acrylic acid or itaconic acid (especially diesters are preferred when itaconic acid is used), monofunctional compounds represented by general formula [2] organosiloxane is
60 parts by weight or less, about 0.5 to 15 parts by weight of diesters, triesters, and tetraesters of polyhydric alcohols and methacrylic acid or acrylic acid, monoesters of polyhydric alcohols and methacrylic acid or acrylic acid, and monohydric alcohols. A monoester of itaconic acid, a monoester of fluoroalkyl alcohol and itaconic acid, or a hydrophilic monomer such as methacrylic acid in a proportion of about 5 to 10 parts by weight is copolymerized instead of these esters. Something is desirable. Then, dimethyl-2,2'-azobisisobutyrate, 2,2'-
Azobis(4-methoxy-2,4-dimethylvaleronitrile), 2,2'-azobis(2,4-dimethylvaleronitrile), 2,2'-azobisisobutyronitrile, benzoyl peroxide, di-
tert-butyl peroxide, methyl ethyl ketone peroxide, isobutyl peroxide,
A polymerization initiator such as diisopropyl peroxydicarbonate is blended, and polymerization is carried out by an ordinary radical polymerization method. Incidentally, for example, 1,5-bis(methacryloxyethoxypropyl)-1,1,3,3,5,5-(hexamethyl)trisiloxane (referred to as BiMAPPS-1) contained in the above-mentioned polyfunctional organosiloxane.
can be obtained as follows. First, methacrylic acid allyloxyethyl ester (boiling point 2 mmHg - 64 to 65°C, n ²⁰ _D = 1.4463) was produced with a yield of about 80% using methacrylic acid and allyloxyethanol under a sulfuric acid catalyst using a normal esterification method. Get it at a rate. Then, about 1 mole of allyloxyethyl methacrylate and 10 ^-5 moles of platinum catalyst were added to a three-necked flask equipped with a reflux condenser, thermometer, dropping funnel, and stirrer, and heated to about 50°C. Then 0.4 mol of 1,1,3,3,5,5-hexamethyltrisiloxane is added dropwise. and,
The reaction was carried out with stirring while maintaining the temperature at 50°C, and then unreacted allyloxyethyl methacrylate and 1,1,3,3,5,5-hexamethyltrisiloxane were distilled off under reduced pressure. -bis(methacryloxyethoxypropyl)-1,1,3,
3,5,5-hexamethyltrisiloxane get. For example, 1,3-bis(methacryloxyethoxypropyl)-1,1,3,3-tetramethyldisiloxane (referred to as BiMAPPS-2) can be obtained as follows. In the same manner as above, 1, 1, 3, 3, 5, 5
-hexamethyltrisiloxane 1,1,3,3
-tetramethyldisiloxane, 1,3-bis(methacryloxyethoxypropyl)-1,1,3,3-tetramethyldisiloxane can be obtained. Also, for example, 1,3-bis(methacryloxyethoxypropyl)-1,1,3,3-tetrakis [bis(trimethylsiloxy)methylsiloxy]
Disiloxane (referred to as BiMAPPS-3) is obtained as follows. First, methacrylic acid allyloxyethyl ester is obtained in the same manner as described above. Then, about 1 mole of the above allyloxyethyl methacrylate and 10 ^-5 moles of platinum catalyst were added to a three-necked flask equipped with a reflux condenser, thermometer, dropping funnel, and stirrer, and heated to about 75°C. Then 1.1 mol of trichlorosilane is added dropwise.
Then, the reaction is carried out while stirring while maintaining the temperature at 75 to 80°C, and then unreacted allyloxyethyl methacrylate and trichlorosilane are distilled off under reduced pressure to obtain methacryloxyethoxypropyltrichlorosilane. By reacting the thus obtained methacryloxyethoxypropyltrichlorosilane with methanol in the presence of pyridine in an ether solvent, methacryloxyethoxypropyltrimethoxysilane (boiling point 4 mmHg-125°C) is obtained. Also, add 39 ml of concentrated sulfuric acid to 44 ml of absolute ethanol while stirring.
and 50 ml of distilled water gradually added to the mixture,
Make an ethyl sulfate catalyst solution. Next, 1 mole of methacryloxyethoxypropyltrimethoxysilane was mixed with 2 moles of 1,1,1,3,5,5,5-heptamethyl-3-acetoxytrisiloxane in a flask equipped with a magnetic stirrer, The flask is cooled in an ice bath and 50 ml of the ethyl sulfuric acid catalyst prepared above is added dropwise from the dropping funnel into the stirred mixture. After adding the catalyst,
The reaction mixture is stirred at room temperature for 48 hours. The upper oil layer was separated, washed with sodium hydrogen carbonate solution, washed with water, dried over anhydrous sodium sulfate, and then the low-boiling components were distilled off under reduced pressure to obtain 1,3-bis(methacryloxyethoxypropyl)-1. ,1,
3,3-tetrakis[bis(trimethylsiloxy)methylsiloxy]disiloxane is obtained. For example, tris(methacryloxyethoxypropyldimethylsiloxy)methylsilane (referred to as TriMAPPS-1) can be obtained as follows. First, methacrylic acid allyloxyethyl ester is obtained in the same manner as in the above case. Then, about 1 mole of the above allyloxyethyl methacrylate and 10 ^-5 moles of platinum catalyst were added to a three-necked flask equipped with a reflux condenser, thermometer, dropping funnel, and stirrer, and heated to about 75°C. Then 1.1 mol of dimethylethoxysilane is added dropwise. Then, the reaction is carried out while stirring while maintaining the temperature at 75 to 80°C, and then unreacted allyloxyethyl methacrylate and dimethylethoxysilane are distilled off under reduced pressure to obtain methacryloxyethoxypropyldimethylethoxysilane. 3 moles of methacryloxyethoxypropyldimethylethoxysilane thus obtained were mixed with 1 mole of methyltriacetoxysilane in a flask equipped with a magnetic stirrer, the flask was cooled in an ice bath and the procedure was repeated as before. 50 ml of the prepared ethyl sulfuric acid catalyst is dropped into the stirred reaction mixture from the dropping funnel. After addition of the catalyst, the reaction mixture is stirred at room temperature for 48 hours. Then, the upper oil layer was separated, washed with sodium bicarbonate solution, washed with water, and dried with anhydrous sodium sulfate.
Distill low-boiling substances under reduced pressure to obtain tris(methacryloxyethoxypropyldimethylsiloxy)methylsilane. get. For example, 1,3,5-tris(methacryloxyethoxypropyl)-1,3,5,7-tetramethyl-7-propylcyclotetrasiloxane (referred to as TriMAPPS-2) can be obtained as follows. It will be done. First, methacrylic acid allyloxyethyl ester is obtained in the same manner as described above. Then, about 1 mole of the above allyloxyethyl methacrylate and 10 ^-5 moles of platinum catalyst were added to a three-necked flask equipped with a reflux condenser, thermometer, dropping funnel, and stirrer, and heated to about 50°C. Then 0.3 mol of 1-propyl-1,3,5,7-tetramethylcyclotetrasiloxane is added dropwise. The reaction was carried out while stirring at 50°C, and then the unreacted allyloxyethyl methacrylate and 1-propyl-1,
3,5,7-tetramethylcyclotetrasiloxane was distilled off to give 1,3,5-tris(methacryloxyethoxypropyl)-1,3,5,7-tetramethyl-7-propylcyclotetrasiloxane. get. Examples 1 to 9 5 to 80 parts by weight of BiMAPPS-1, 7 to 82 parts by weight of methyl methacrylate (hereinafter referred to as MMA) as an ester of monohydric alcohol and methacrylic acid, and 8 parts by weight of methacrylic acid (hereinafter referred to as MA) as a hydrophilic monomer. V-65 (trade name, 2,2'-azobis(2,4-dimethyl) Add 0.01 part by weight of a polymerization initiator of parellonitrile), pour this into a cylindrical polypropylene polymerization mold with a diameter of 16 mm and a height of 10 mm, replace the upper space with nitrogen, and then place it in an oven that has been replaced with nitrogen. The polymerization was maintained at 40°C for 20 hours, then at 70°C and 90°C for 10 hours each, and then at 100°C for 10 hours to complete the polymerization, yielding a colorless, transparent, hard rod-shaped block. Then, this rod-shaped block is subjected to normal processing to obtain a contact lens. The characteristics of the contact lenses thus obtained are shown in Table 1.

【table】

[Table] Examples 10-22 BiMAPPS-2 45 parts by weight, C ₁ - shown in Table 2
42 parts by weight of an ester consisting of a _C10 monohydric alcohol and an acid selected from the group consisting of methacrylic acid, acrylic acid, and itaconic acid, 8 parts by weight of hydrophilic monomers MA, 5 parts by weight TGD, V-601 (trade name) A colorless, transparent, hard rod-shaped block was obtained in the same manner as in Example 1 using 0.03 part by weight of dimethyl-2,2'-azobisisobutyrate, and this was processed to obtain a contact lens. The characteristics of the contact lenses thus obtained are shown in Table 2.

[Table] M-A: Methyl acrylate n-HMA: n-hexyl methacrylate CHMA: Cyclohexyl methacrylate Di-MITA: Dimethyl itaconate i-BMA: Isobutyl methacrylate PeA: Pentyl acrylate EMA: Ethyl methacrylate Di-PeITA: Dipentyl itaconate Mo -EITA: Monoethyl itaconate Mo-n-BITA: Mono-n-butyl itaconate Mo-2-EHITA: Mono-2-ethylhexyl CHA: Cyclohexyl acrylate PMA: Propyl methacrylate Mo-MITA: Monomethyl itaconate Di-n- HITA: di-n-hexyl itaconate n-HA: n-hexyl acrylate PeMA: pentyl methacrylate Examples 23-44 Consisting of 30-60 parts by weight of various organosiloxanes, monohydric alcohol, methacrylic acid, acrylic acid, itaconic acid 27 to 57 parts by weight of an ester consisting of an acid selected from the group, 8 parts by weight of MA, 5 parts by weight of TGD,
Using 0.01 part by weight of V-65, a colorless, transparent, hard rod-shaped block was obtained in the same manner as in Example 1, and this was processed to obtain a contact lens. The characteristics of the contact lenses thus obtained are shown in Table 3.

【table】

[Table] Examples 45-58 30-60 parts by weight of various organosiloxanes as esters of monohydric alcohol and methacrylic acid
EMA52 parts by weight or less, esters of linear or branched fluoroalkyl alcohols having 1 to 20 fluorine atoms and methacrylic acid, acrylic acid, itaconic acid, 5 to 35 parts by weight, MA8 parts by weight,
Using 5 parts by weight of TGD and 0.01 parts by weight of V-65, a colorless, transparent and hard rod-shaped block was obtained in the same manner as in Example 1, and this was processed to obtain a contact lens. The characteristics of the contact lenses thus obtained are shown in Table 4.

[Table] Examples 59 to 73 5 to 80 parts by weight of various organosiloxanes, 95 parts by weight or less of esters of monohydric alcohols and methacrylic acid, acrylic acid, or itaconic acid, fluoroalkyl alcohols and methacrylic acid, acrylic acid, or itaconic acid 95 parts by weight or less of diesters, triesters, and tetraesters of polyhydric alcohol and methacrylic acid or acrylic acid as crosslinking agents, 15 parts by weight or less of diesters, triesters, and tetraesters of polyhydric alcohol and methacrylic acid or acrylic acid as hydrophilic monomers. monoester of monohydric alcohol and itaconic acid, monoester of fluoroalkyl alcohol and itaconic acid, 10 parts by weight or less of methacrylic acid, acrylic acid or N-vinylpyrrolidone, 0.01 part by weight or less of free radical polymerization initiator A colorless, transparent, hard rod-shaped block is obtained in the same manner as in Example 1, and this is processed to obtain a contact lens. The characteristics of the contact lenses thus obtained are shown in Table 5.

【table】

【table】

Claims (1)

[Claims] 1. General formula (However, X ₁ to _{X 6} are selected from the group consisting of C ₁ to _{C 5} alkyl groups, aromatic groups, and Y groups, and Y group is (However, at least two or more of X ₁ to X ₆ are Y groups), R ₂ is CH ₃ or H, R ₁ ,
R ₁ ″ is a C ₁ to C ₅ alkyl group, an aromatic group, and Z
Z group is [Formula] and R ₁ ′ does not represent a group but represents a bonded chain R ₁ ′-O-R ₁ ′ or a C ₁ to C ₅ alkyl group. , aromatic group and Z group, l, m,
k, l', m', k' are integers of 0 to 10, n is an integer of 1 to 10, and j is ₀ or ₁ ); an ester consisting of a hydric alcohol and an acid selected from the group consisting of methacrylic acid, acrylic acid, and itaconic acid; and/or a linear or branched fluoroalkyl alcohol having 1 to 20 fluorine atoms and methacrylic acid; A contact lens material characterized in that it is copolymerized using at least an ester consisting of an acid selected from the group consisting of acrylic acid and itaconic acid.