JPH0160124B2 - - Google Patents

Description

[Detailed description of the invention]

[Industrial Application Field] The present invention relates to contact lens materials, and particularly to contact lenses that have excellent oxygen permeability and hydrophilicity, can be worn continuously for long periods of time, and are easy to handle. [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. Lenses have good hydrophilicity, which makes them comfortable to wear to some extent, but they do not have sufficient oxygen permeability, so they cannot be worn continuously for long periods of time.Furthermore, they are water-containing, so hard contact lenses are recommended. It has the disadvantage that it is more troublesome to handle than . In addition, in order to enable continuous wear, contact lenses with high water content containing, for example, N-vinylpyridone as a main component have been proposed, and these have favorable features in terms of hydrophilicity and oxygen permeability. ,
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 vinylpyridone-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 devised the following general formula [] (However, A ₁ to _{A 5} are alkyl groups having 1 to 5 carbon atoms,
selected from the group consisting of aromatic groups, D groups and E groups, where the D group is

[Formula], R ₄ is a methyl group or a hydrogen atom, R ₅ to R ₈ , R′ ₆ , R′ ₈
is an alkyl group having 1 to 5 carbon atoms, an aromatic group, and G
G group is selected from the group consisting of

[Formula], R ₉ , R' ₉ , R'' ₉ are selected from the group consisting of an alkyl group having 1 to 5 carbon atoms and an aromatic group, and R' ₅ and R' ₇ do not represent a group and R ' ₅ -O-R' ₇ or an alkyl group having 1 to 5 carbon atoms,
selected from the group consisting of an aromatic group and a G group, b,
b', c, c' are integers from 0 to 10, d is an integer from 1 to 10, and the E group is

[Formula] (e is 1 to 5, f is 2 to 3, g is 0 to 5, k is an integer of 1 to 3, R ₁₀ is a hydrogen atom or carbon number 1 to 5
an alkyl group, R ₁₁ is a hydrogen atom or a methyl group)) and an organosiloxane represented by the following general formula (However, X is a fluorine atom or a Z group, and the Z group is

[Formula] Q is - (CH ₂ ) _q - or

[Formula] q is an integer from 0 to 10, r is an integer from 2 to 5, and Y is an integer from 2 to 5.

[Formula] R ₁ and R ₂ are methyl group or hydrogen atom, R ₃ is fluorine atom or CR ₃ , j and k are 1 to 4
p is an integer of 0 to 5, m and n are integers of 0 to 200);
Ester and/or ester consisting of a monohydric or polyhydric alcohol having 1 to 10 carbon atoms and an acid selected from the group consisting of methacrylic acid, acrylic acid, and itaconic acid.
A material made of a copolymer copolymerized using at least an ester consisting of a linear or branched fluoroalkyl alcohol having fluorine atoms and an acid selected from the group consisting of methacrylic acid, acrylic acid, and itaconic acid. has excellent oxygen permeability and hydrophilicity, and contact lenses made of such materials are easy to handle and have excellent durability.
Moreover, they found that it is comfortable to wear and can be worn continuously for a long time, and furthermore, it has excellent vision correction effects and dimensional stability. The organosiloxane represented by the above general formula [] includes, for example, methacryloxyethoxypropylpentamethyldisiloxane, acryloxyethoxypropylpentamethyldisiloxane, methacryloxyethoxypropylheptamethyltrisiloxane, acryloxyethoxypropylheptamethyltrisiloxane, and acryloxyethoxypropylheptamethyltrisiloxane. Siloxane, 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,
Acryloxyethoxypropyltetramethyltripropylcyclotetrasiloxane, 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, 1,3-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, [tris(acryloxyethoxypropyl)dimethylsiloxy]-methylsilane, [tris(methacryloxyethoxypropyl)dimethylsiloxy]-methylsilane, 1,5-bis(methacryloxyethoxypropyl)-1, 1,3,3,5,5-(hexamethyl)trisiloxane, 1,3,5-tris(methacryloxyethoxypropyl)-1,
3,5,7-(tetramethyl)-7-(propyl)cyclotetrasiloxane, 1-methacryloxyethoxypropyl-3-(acetoxypropyl)-1,1,3,3-(tetramethyl)disiloxane, methacrylic Roxyethoxypropyl-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-acetoxyethoxypropyl-1,1,3,3-tetramethyldisiloxane, 1-methacryloxyethoxypropyl-5-[(acetoxypropyloxycarbonyl)ethyl]-3,7-dipropyl-
1,3,5,7-(tetramethyl)tetracycloxane, 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-pentaoxyoctadecyl-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-trioxydecyloxycarbonyl)ethyl]-
1,1,3,3,5,5-(hexamethyl)trisiloxane, 1,3-bis(methacryloxyethoxypropyl)-1,1,3,3-tetrakis(acetoxypropyltetramethyldisiloxy)
Disiloxane, 1-methacryloxyethoxypropyl-9-[(acetoxyisopropyloxycarbonyl)ethyl)decamethylpentasiloxane, 1-methacryloxyethoxypropyl-5-
[(dihydroxypropyloxy)propyl]-
Examples include 1,1,3,3,5,5-(hexamethyl)trisiloxane. In addition, as the perfluoroalkyl ether monomer shown in the above general formula [], for example, etc. Further, 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 methacrylate,
Dimethyl itaconate, monomethyl itaconate, ethyl methacrylate, ethyl methacrylate, 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, silohexyl methacrylate, cyclohexyl acrylate, dicyclohexyl itaconate,
Monocyclohexyl itaconate, 2-ethylhexyl methacrylate, 2-ethylhexyl acrylate, di2-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-butanediol diacrylate, 1,6-hexanediol dimethacrylate, 1,6-hexanediol acrylate, neopentyl glycol dimethacrylate, neopentyl glycol diacrylate, trimethylolpropane trimethacrylate, trimethylolpropane triacrylate, pentaerythritol Tetra methacrylate, pentaerythritol tetraacrylate, ethylene glycol monomethacrylate, ethylene glycol monoacrylate, diethylene glycol monomethacrylate, diethylene glycol monoacrylate, triethylene glycol monomethacrylate, triethylene glycol monoacrylate, 2-hydroxypropyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxybutyl methacrylate, 2-hydroxybutyl acrylate, 2-hydroxystyrene methacrylate, 2
-Hydroxystyrene acrylate, etc. 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, 2,2,3,3-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-hexafluoroisopropyl itaconate, hexafluoroisopropyl itaco Nate,
Examples include 1H, 1H-heptafluorobutyl methacrylate, 1H, 1H-heptafluorobutyl acrylate, and bis 1H, 1H-heptafluorobutyitaconate. These esters mainly act together with the organosiloxane to improve the oxygen permeability of the polymer material, and also improve the optical transparency. Further, the proportions of the organosiloxane, perfluoroalkyl ether, and various esters constituting the copolymer as a material for contact lenses are about 5 to 80 parts by weight, about 5 to 45 parts by weight, and about 5 parts by weight, respectively.
-80 parts by weight are preferred, and even more preferably esters of monohydric alcohol and methacrylic acid or acrylic acid or diesters of monohydric alcohol and itaconic acid are preferred among about 5 to 80 parts by weight of various esters. About 5 to 80 parts by weight of esters of fluoroalkyl alcohols and methacrylic acid, acrylic acid or itaconic acid (especially diesters are preferred when itaconic acid is used).
50 parts by weight or less, about 15 parts by weight or less of diesters, triesters, and tetraesters of polyhydric alcohols and methacrylic acid or acrylic acid, monoesters of polyhydric alcohols and methacrylic acid or acrylic acid, monohydric alcohols and itacon A monoester with an acid, a monoester with a fluoroalkyl alcohol and itaconic acid, or a copolymer of a hydrophilic monomer such as methacrylic acid in a proportion of about 20 parts by weight or less instead of these esters. 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 peroxycarbonate is blended, and polymerization is carried out by an ordinary radical polymerization method. Example 1 55 parts by weight of methacryloxyethoxypropylpentamethyldisiloxane (hereinafter abbreviated as METS-1) as the organosiloxane monomer represented by the general formula [], and PFE- as the perfluoroalkyl ether represented by the general formula [] 1 5 parts by weight, 27 parts by weight of methyl methacrylate (hereinafter abbreviated as MMA), ethylene glycol dimethacrylate (hereinafter abbreviated as EDMA) as a crosslinkable monomer
V-65 (trade name: 2,2'-azobis(2,4-dimethylvaleronitrile)) was added to a mixture of 5 parts by weight and 8 parts by weight of methacrylic acid (hereinafter abbreviated as MA) as a hydrophilic monomer. 0.01 part by weight of a polymerization initiator was added, and this was poured into a cylindrical polypropylene polymerization mold with a diameter of 16 mm and a height of 10 mm. After purging the upper space with nitrogen, the mixture was heated at 40°C for 20 hours in an oven purged with nitrogen. After that, it was kept at 70°C and 90°C for 10 hours each, and then at 100°C for 10 hours to complete the polymerization, and a colorless and transparent rod-shaped block was obtained. 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. Example 2 Methacryloxyethoxypropyltris(trimethylsiloxy)silane (hereinafter referred to as
METS-2) 35 parts by weight and 1,3-bis(methacryloxyethoxypropyl)-1,
1,3,3-(tetramethyl)disiloxane (hereinafter abbreviated as METS-3) 10 parts by weight, general formula []
Perfluoroalkyl ether represented by: 15 parts by weight of PFE-2, 22 parts by weight of MMA, 5 parts by weight of dimethyl itaconate (hereinafter abbreviated as Di-MITA), 8 parts by weight of MA as a hydrophilic monomer, crosslinkable monomer In a mixture of 5 parts by weight of triethylene glycol dimethacrylate (hereinafter abbreviated as TGD),
Adding 0.03 parts by weight of V-601 (trade name: dimethyl-2,2'-azobisisobutyrate), a colorless and transparent rod-shaped block was obtained in the same manner as in Example 1, and this was processed to form contact lenses. get. The characteristics of the contact lenses thus obtained are shown in Table 1. Example 3 20 parts by weight of acryloxyethoxypropyltetramethyltripropylcyclotetrasiloxane (hereinafter abbreviated as METS-4) and 1-methacryloxyethoxypropyl-3-(acetoxy propyl)-1,1,3,3-(tetramethyl)disiloxane (hereinafter abbreviated as METS-5) 5
Parts by weight, 45 parts by weight of PFE-3 as a perfluoroalkyl ether represented by the general formula [],
12 parts by weight of ethyl methacrylate (hereinafter abbreviated as EMA), cyclohexyl methacrylate (hereinafter referred to as CHMA)
), 4 parts by weight of MA as a hydrophilic monomer, 3 parts by weight of EDMA and 3 parts by weight of tetraethylene glycol dimethacrylate (hereinafter abbreviated as TEGD) as a crosslinking monomer, and 0.01 part by weight of V-65. A colorless and transparent 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 1. Example 4 50 parts by weight of METS-2 as the organosiloxane monomer represented by the general formula [] 10 parts by weight of PFE-4 as the perfluoroalkyl ether represented by the general formula [], 16 parts by weight of MMA,
10 parts by weight of 2,2,2-trifluoroethyl methacrylate (hereinafter abbreviated as FM-1), 8 parts by weight of MA as a hydrophilic monomer, as a crosslinking monomer
EDMA3 parts by weight and TGD3 parts by weight, V-65 0.01
A colorless and transparent 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 1.

[Table] Examples 5 to 27 5 to 80 parts by weight of various organosiloxane monomers represented by the general formula [], 5 to 45 parts by weight of various perfluoroalkyl ether monomers represented by the general formula [], 80 parts by weight or less of esters of monohydric alcohol and methacrylic acid, acrylic acid or itaconic acid, esters of fluoroalkyl alcohol and methacrylic acid, acrylic acid or itaconic acid
50 parts by weight or less, 15 parts by weight or less of diesters, triesters, and tetraesters of polyhydric alcohol and methacrylic acid or acrylic acid as crosslinking agents, monomers of polyhydric alcohol and methacrylic acid or acrylic acid as hydrophilic monomers Using ester, 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, and 0.01 part by weight or less of a free radical polymerization initiator. A colorless and transparent 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 2.

【table】

【table】

Claims (1)

[Claims] 1. General formula (However, A ₁ to _{A 5} are alkyl groups having 1 to 5 carbon atoms,
selected from the group consisting of aromatic groups, D groups and E groups, D group is [Formula], R ₄ is a methyl group or a hydrogen atom, R ₅ to R ₈ , R' ₆ , R' ₈
is an alkyl group having 1 to 5 carbon atoms, an aromatic group, and G
The G group is [Formula], _R9 , _R'9 , _R''9 are selected from the group consisting of an alkyl group having 1 to 5 carbon atoms, an aromatic group, and _R'5 , R' ₇ does not represent a group but represents a bonding chain of R' ₅ -O-R' ₇ or an alkyl group having 1 to 5 carbon atoms,
selected from the group consisting of an aromatic group and a G group, b,
b', c, c' are integers from 0 to 10, d is an integer from 1 to 10, and the E group is [Formula] (e is 1 to 5, f is 2 to 3, g is 0 to 5, k is an integer of 1 to 3, R ₁₀ is a hydrogen atom or a carbon number of 1 to 5
an alkyl group, R ₁₁ is a hydrogen atom or a methyl group)) and an organosiloxane represented by the general formula (However, X is a _fluorine atom or _a Z group, and the Z group is [formula] , Y is [Formula] R ₁ , R ₂ is a methyl group or a hydrogen atom, R ₃ is a fluorine atom or CF ₃ , j and k are 1 to 4
p is an integer of 0 to 5, m and n are integers of 0 to 200);
Ester and/or ester consisting of a monohydric or polyhydric alcohol having 1 to 10 carbon atoms and an acid selected from the group consisting of methacrylic acid, acrylic acid, and itaconic acid.
characterized by copolymerization using at least an ester consisting of a linear or branched fluoroalkyl alcohol having fluorine atoms and an acid selected from the group consisting of methacrylic acid, acrylic acid, and itaconic acid. contact lens materials. 2. The contact lens material according to claim 1, wherein the weight ratio of organosiloxane to perfluoroalkyl ether to ester is 5 to 80:5 to 45:5 to 80.