JPH0117129B2 - - 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 since 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 [1] (However, Y ₁ to Y ₅ groups are selected from the group consisting of C ₁ to _{C 5} alkyl groups, aromatic groups, and Z groups, and at least one of Y ₁ to Y ₅ groups is a Z group, and The base is , R ₂ is CH ₃ or H, and R ₁ and R ₁ ″ are C ₁ to
selected from the group consisting of C ₅ alkyl groups, aromatic groups, and W groups, where the W group is

[Formula], Ra is a C ₁ to C ₅ alkyl group or aromatic group,
R ₁ ′ does not represent a group but represents a bonded chain R ₁ ′-O-R ₁ ′, or is selected from the group consisting of a C ₁ to _{C 5} alkyl group, an aromatic group, and a W group, l, l', m,
m' is an integer from 0 to 10, n is an integer from 1 to 10, _and the Z group is -( _CH2 ) ₃ -O-( _CH2CH2O )p-
_R3 ,

【formula】

or

[Formula], p is an integer of 1 to 5, q is an integer of 2 to 3, r is 0 to
an integer of 5, s is an integer of 1 to 3, _R2 is a hydrogen atom or a _C1 to _C5 alkyl group, and _R4 is _a hydrogen atom or _a methyl group); ester consisting of a monohydric or polyhydric alcohol and an acid selected from the group consisting of methacrylic acid, acrylic acid, and itaconic acid, and/or a linear or branched fluoroalkyl having 1 to 20 fluorine atoms. A material made of a copolymer copolymerized using at least an ester consisting of an alcohol and an acid selected from the group consisting of methacrylic acid, acrylic acid, and itaconic acid has excellent oxygen permeability and hydrophilicity, and is substantially non-containing. Contact lenses made of water-containing materials are easy to handle, have excellent durability, are comfortable to wear, can be worn continuously for long periods of time, and have excellent vision correction effects and dimensional stability. I found it to be excellent. In addition, as the organosiloxane represented by the above general formula [1], for example, 1-Methacryloxyethoxypropyl-3-
(acetoxypropyl)-1,1,3,3-(tetramethyl)disiloxane, methacryloxyethoxypropyl-tris(acetoxyethyldimethylsiloxy)silane, 1,3-bis(methacryloxyethoxypropyl)-1,1,3,3-tetrakis(acetoxyethyldimethylsiloxy)disiloxane, methacryloxyethoxypropyl-tris(carboxyethyldimethylsiloxy)silane, 1-Methacryloxyethoxypropyl-5-
[(methoxyethoxyethoxycarbonyl)ethyl]-1,1,3,3,5,5-hexamethyldisiloxane, 1-methacryloxyethoxypropyl-3-acetoxypropyl-1,1,3,3-tetramethyldisiloxane, 1-Methacryloxyethoxypropyl-5-
[(acetoxypropyloxycarbonyl)ethyl]-3,7-dipropyl-1,3,5,7-(tetramethyl)tetracyclosiloxane, 1-methacryloxyethoxypropyl-1,
3,5,7-(tetramethyl)-3,5,7-tri(acetoxyethyl)tetracyclosiloxane, 1-Methacryloxyethoxypropyl-3-
(Hydroxyethoxypropyl)-1,1,3,3
-(tetramethyl)disiloxane, 1-acryloxyethoxypropyl-3-(4,
7,10,13,16-pentaoscyoctadecyl-18
-ol)-1,1,3,3-(tetramethyl)disiloxane, 1-Methacryloxyethoxypropyl-3-
(12-acetoxy-4,7,10-trioxidedodecyl)-1,1,3,3-(tetraphenyl)disiloxane, 1-acryloxyethoxypropyl-3-(4,
7,10,13-tetraoxyhexadecyl)-1,
1,3,3-(tetrapentyl)disiloxane 1-Methacryloxyethoxypropyl-19-
(acetoxypropyl) icosamethyldecasiloxane, 1-acryloxyethoxypropyl-3-
[(3,6-dioxyoctyl-8-ol-1-
oxycarbonyl)ethyl]-1,1,3,3-
(tetramethyl)disiloxane, 1-Methacryloxyethoxypropyl-3-
[(hydroxyethyloxycarbonyl)propyl]-1,1,3,3-(tetramethyl)disiloxane, 1-acryloxyethoxypropyl-5-
[(1,4,7-trimethyl-3,6,9-trioxadecyloxycarbonyl)ethyl]-1,1,
3,3,5,5-(hexamethyl)trisiloxane, 1,3-bis(methacryloxyethoxypropyl)-1,1,3,3-tetrakis(acetoxypropyltetramethyldisiloxasi)disiloxane, 1-Methacryloxyethoxypropyl-9-
[(acetoxyisopropyloxycarbonyl)ethyl]decamethylpentasiloxane, 1-Methacryloxyethoxypropyl-5-
[(dihydroxypropyloxy)propyl]-1,
Examples include 1,3,3,5,5-(hexamethyl)trisiloxane. 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. 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 polyhydric alcohols Monoesters of methacrylic acid or acrylic acid, or monoesters of itaconic acid and monohydric alcohol are mainly used to improve the hydrophilicity of polymer materials. still,
Methacrylic acid, acrylic acid, acrylamide,
It is also possible to use methacrylamide, N-methylolmethacrylamide, N-vinylpyrrolidone, and the like. 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-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-heptadecafluorodecyl itaconate,
1H,1H-pentadecafluorooctyl methacrylate, 1H,1H-pentadecafluorooctyl acrylate, 1H,1H-pentadecafluorooctyl itaconate, bis-1H,1H-pentadecafluorooctyl itaconate, 1H,1H-pentafluoro Propyl methacrylate, 1H, 1H
-Pentafluoropropyl acrylate, bis-
1H, 1H-pentafluoropropyl itaconate, 1H, 1H-pentafluoropropyl itaconate, hexafluoroisopropyl methacrylate, hexafluoroisopropyl acrylate,
Bishexafluoroisopropyl itaconate,
Hexafluoroisopropyl itaconate, 1H,
1H-heptafluorobutyl methacrylate,
1H,1H-heptafluorobutyl acrylate,
Examples include 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. ) Monofunctional organosiloxane and/or general formula [3] (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], where Ra is a C ₁ to C ₅ alkyl group or an aromatic group,
R ₁ ′ does not represent a group but represents a bonded chain R ₁ ′-O-R ₁ ′, or is selected from the group consisting of a C ₁ to _{C 5} alkyl group, an aromatic group, and a Z group; , l', m' are integers of 0 to 10, and n is an integer of 1 to 10). 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. Further, as the organosiloxane represented by the above general formula [3], 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,
Examples include 7-tetrakis(methacryloxyethoxypropyl)-1,3,5,7-(tetramethyl)cyclotetrasiloxane, [tris(acryloxyethoxypropyl)dimethylsiloxy]-methylsilane, and the like. 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. For 5 to 80 parts by weight of organosiloxane,
About 5 to 95 parts by weight of esters of monohydric alcohols and methacrylic acid or acrylic acid or diesters of monohydric alcohols and itaconic acid, esters of fluoroalkyl alcohols and methacrylic acid, acrylic acid or itaconic acid (especially itaconic acid) 50 parts by weight or less of an organosiloxane represented by the general formula [2] or [3], a diester of a polyhydric alcohol and methacrylic acid or acrylic acid,
About 0.5 to 15 parts by weight of triesters and tetraesters, monoesters of polyhydric alcohol and methacrylic acid or acrylic acid, monoesters of monohydric alcohol and itaconic acid, monoesters of fluoroalkyl alcohol and itaconic acid, Alternatively, in place of these esters, it is desirable to copolymerize a hydrophilic monomer such as methacrylic acid in an amount of about 5 to 10 parts by weight. 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. In addition, for example, 1-methacryloxyethoxypropyl-3-(acetoxypropyl)-1,1, which is contained in the organosiloxane of the general formula [1],
3,3-tetramethyldisiloxane is obtained as follows. First, methacrylic acid allyloxyethyl ester (boiling point: 2 mmHg - 64 to 65°C, ^n20D = 1.4463) is obtained by a normal esterification method using methacrylic acid and _{allyloxyethanol} under a sulfuric acid catalyst. Then, about 1 mole of allyl acetate 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
After heating to ℃, 1, 1, 3, 3 from the dropping funnel.
- about 1 mol of tetramethyldisiloxane is added dropwise,
The reaction is carried out while stirring while maintaining the temperature at 90°C, and then distillation is carried out under reduced pressure to obtain 1-acetoxypropyl-1,1,3,3-tetramethyldisiloxane. Next, a reaction mixture of 1 mole of allyloxyethyl methacrylate and 10 ^-5 moles of platinum catalyst was added.
After heating to 75°C, 1 mol of 1-acetoxypropyl-1,1,3,3-tetramethyldisiloxane obtained above was added dropwise, and the reaction was carried out while maintaining the temperature at 75°C with stirring. , unreacted allyloxyethyl methacrylate and 1-
Acetoxypropyl-1,1,3,3-tetramethyldisiloxane was distilled off, and 1-methacryloxyethoxypropyl-3-(acetoxypropyl)-
1,1,3,3-(tetramethyl)disiloxane is obtained. For example, 1-methacryloxyethoxypropyl-tris(acetoxyethyldimethylsiloxy)silane can be obtained as follows. First, allyloxyethyl methacrylate was obtained in the same manner as above, and about 1 mole of allyloxyethyl methacrylate and platinum were placed in a three-necked flask equipped with a reflux condenser, thermometer, dropping funnel, and stirrer. 10 ⁻⁵ moles of catalyst are added and warmed to about 75° C., then 1.1 moles of trichlorosilane are 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. Next, in a three-necked flask equipped with a stirrer, a thermometer, and a dropping funnel, a solution of 0.3 mol of the above methacryloxyethoxypropyltrichlorosilane and 1.8 mol of acetoxyethyldimethylchlorosilane dissolved in 3 mol of isopropyl alcohol was added, and the mixture was heated to 0 to 10°C. The reaction mixture is kept at temperature and 4 moles of distilled water are added to carry out the cohydrolysis. Then, the upper organic layer is separated, washed with an aqueous sodium bicarbonate solution and distilled water, and then anhydrous sodium sulfate is removed. After that, an appropriate amount of activated carbon is added to decolorize, and then filtered through a membrane filter (0.2μ) to reduce the When the boiling point is distilled off under reduced pressure, 1-
Methacryloxypropyl-tris(acetoxyethyldimethylsiloxy)silane is obtained. Also, for example, 1-methacryloxyethoxypropyl-3-(hydroxyethoxypropyl)-1,
1,3,3-Tetramethyldisiloxane is obtained as follows. First, allyloxyethyl methacrylate was obtained in the same manner as above, and in a three-necked flask equipped with a reflux condenser, a thermometer, a dropping funnel, and a stirrer, about 1 mole of allyloxyethoxytrimethylsilane and 10 ^-5 platinum catalyst were placed. mol and after heating to 90°C, 1, 1,
Approximately 1 mole of 3,3-tetramethyldisiloxane was added dropwise, the reaction was carried out while stirring at 90°C, and then distillation was performed under reduced pressure to obtain 1-trimethylsiloxyethoxypropyl-1,1,3,3 - Tetramethyldisiloxane is obtained. Next, a reaction mixture of 1 mole of allyloxyethyl methacrylate and 10 ^-5 moles of platinum catalyst was added.
After heating to 75°C, 1-trimethylsiloxyethoxypropyl-1,1,3,3- obtained above
Add 1 mol of tetramethyldisiloxane dropwise and heat to 75°C.
The reaction was carried out with stirring at a constant temperature, and then unreacted allyloxyethyl methacrylate and 1-trimethylsiloxyethoxypropyl-1,1,3,3-tetramethyldisiloxane were distilled off under reduced pressure to remove the alcohol. After acid hydrolysis in the solution, the organic layer was separated, washed with an aqueous sodium bicarbonate solution and water, dehydrated with anhydrous sodium sulfate, decolorized with activated carbon, and then the low-boiling substances were distilled off. -methacryloxyethoxypropyl-3-(hydroxyethoxypropyl)-1,1,
3,3-tetramethyldisiloxane is obtained. Also, for example, 1-methacryloxyethoxypropyl-5-(dihydroxypropyloxypropyl)
-1,1,3,3,5,5-hexamethyltrisiloxane is obtained as follows. First, as in the above case, methacrylic acid allyloxyethyl ester is obtained by a normal esterification method using methacrylic acid and allyloxyethanol under a sulfuric acid catalyst. Then, 1 mole of ketal allyl ether obtained by reacting allyl glycidyl ether and acetone in the presence of a boron trifluoride catalyst, and 1,
After reacting 1 mole of 1,3,3,5,5-hexamethyltrisiloxane at 70°C in the presence of 10 ^-5 moles of platinum catalyst, distillation was performed under reduced pressure to form 1-(6,
7-o-isopropylidene-4-oxaheptyl)-1,1,3,3,5,5-hexamethyltrisiloxane is obtained. Next, a reaction mixture prepared by adding 10 ^-5 mol of platinum catalyst to 1 mol of allyloxy methacrylate was heated to 75°C, and the 1-(6,7-o-isopropylidene-4- oxaheptyl)-1,1,3,3,5,5-hexamethyltrisiloxane was added dropwise, and the reaction was carried out with stirring at 75°C, followed by acid hydrolysis and the organic layer was separated. After washing with an aqueous sodium bicarbonate solution and then distilled water, dehydrating with anhydrous sodium sulfate, and decolorizing with activated carbon, low-boiling substances were distilled off under reduced pressure to obtain 1-methacryloxyethoxypropyl-5-(dihydroxy propyloxypropyl)-1,1,3,3,5,
5-hexamethyltrisiloxane is obtained. Examples 1 to 9 5 to 80 parts by weight of MAPS-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. Department,
V-65 (trade name: 2,2'-azobis(2,4-dimethylvaleronitrile) )) Add 0.01 part by weight of polymerization initiator,
This was poured into a cylindrical polypropylene polymerization mold with a diameter of 16 mm and a height of 10 mm, the upper space was replaced with nitrogen, and then placed in an oven that had 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 to obtain 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] Examples 10 to 20 45 parts by weight of MAPS-2, 42 parts by weight of an ester consisting of a C ₁ to C ₁₀ monohydric alcohol shown in Table 2 and an acid selected from the group consisting of methacrylic acid, acrylic acid, and itaconic acid parts, hydrophilic monomer MA8 parts by weight,
A colorless, transparent, hard rod-shaped block was obtained in the same manner as in Example 1 using 5 parts by weight of TGD and 0.03 parts by weight of V-601 (trade name: dimethyl-2,2'-azobisisobutyrate). Process this to obtain contact lenses. The characteristics of the contact lenses thus obtained are shown in Table 2.

[Table] Examples 21 to 49 30 to 60 parts by weight of various organosiloxanes, 27 to 57 parts by weight of EMA as an ester consisting of monohydric alcohol and methacrylic acid, 8 parts by weight of MA, 5 parts by weight of TGD, 0.01 part by weight of V-65. 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 3.

【table】

[Table] Examples 50 to 78 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, methacrylic acid, acrylic acid or N
- Using 10 parts by weight or less of vinylpyrrolidone and 0.01 parts by weight or less of a free radical polymerization initiator, Example 1
A colorless, transparent, hard rod-shaped block is obtained in the same manner as above, and this is processed to obtain a contact lens. The characteristics of the contact lenses thus obtained are shown in Table 4.

【table】

[Table] Examples 79 to 95 50 to 60 parts by weight of various organosiloxanes, 35 parts by weight or less of esters of monohydric alcohol and methacrylic acid or acrylic acid, 10 parts by weight of esters of fluoroalkyl alcohol and methacrylic acid or acrylic acid Below, 15 parts by weight or less of a diester of polyhydric alcohol and methacrylic acid as a crosslinking agent, 10 parts by weight or less of methacrylic acid as a hydrophilic monomer, V-65 0.01
A colorless, transparent, hard rod-shaped block is obtained in the same manner as in Example 1 using parts by weight, and this is processed to obtain a contact lens. The characteristics of the contact lenses thus obtained are shown in Table 5.

【table】

【table】

【table】

Claims (1)

[Claims] 1. General formula (However, Y ₁ to Y ₅ groups are selected from the group consisting of C ₁ to _{C 5} alkyl groups, aromatic groups, and Z groups, and at least one of Y ₁ to Y ₅ groups is a Z group, and The base is , R ₂ is CH ₃ or H, and R ₁ and R ₁ ″ are C ₁ to
selected from the group consisting of a C ₅ alkyl group, an aromatic group, and a W group, where the W group is [Formula], Ra is a C ₁ to C ₅ alkyl group or an aromatic group, and R ₁ ′ is without expressing the base
R ₁ ′-O-R ₁ ′ or selected from the group consisting of C ₁ to C ₅ alkyl groups, aromatic groups, and W groups, where l, l′, m, m′ are 0 is an integer between ~10 and
n is an integer from 1 to 10, _and the Z group is -( _CH2 ) ₃ -O-( _CH2CH2O )p- _R3 , 【formula】 or [Formula], p is an integer of 1 to 5, q is an integer of 2 to 3, r is 0 to
an integer of 5, s is an integer of 1 to 3, _R3 is a hydrogen atom or a _C1 to _C5 alkyl group, and _R4 is _a hydrogen atom or a methyl group) _; ester consisting of a monohydric or polyhydric alcohol and an acid selected from the group consisting of methacrylic acid, acrylic acid, and itaconic acid and/or a linear or branched fluoroalkyl having 1 to 20 fluorine atoms A contact lens material characterized in that it is copolymerized using at least an ester consisting of coal and an acid selected from the group consisting of methacrylic acid, acrylic acid, and itaconic acid.