JPH04168116A - Production of oxygen-permeable polymer material - Google Patents

Abstract

PURPOSE:To obtain the title polymer useful for contact lens, having extremely high oxygen permeability, hardly adhering dirt to the polymer, having excellent cutting properties and abrasiveness by polymerizing a specific polymerizable unsaturated monomer containing a fluoroalkyl group and siloxane bond. CONSTITUTION:At least one kind of a polymerizable monomer (e.g. pentamethyldisiloxanylmethyl methacrylate) shown by formula I [A<1> and A<2> are unsaturated polymerizable group; X<1> to X<3> are 1-4C bifunctional hydrocarbon; R<1> to R<8> are alkyl, phenyl or vinyl which may be replaced with fluorine atom, H or group shown by formula II (R<11> and R<12> are as shown for R<1>; B<1> is unsaturated polymerizable group or H; X<5> is 1-10C bifunctional hydrocarbon; Y is 0-20; R<9> and R<10> are H, F or fluoroalkyl; 1 and w are 0 or 1; n and t are 0-20; q and r are 0-20; q+r>=1] is polymerized or copolymerized to give the objective oxygen permeable polymer material.

Description

Detailed Description of the Invention [Field of Industrial Application] The present invention relates to a method for producing an oxygen-permeable polymer material, and particularly to a method for producing an oxygen-permeable polymer material that is extremely useful as an ophthalmic material such as contact lenses and intraocular lenses. Regarding the manufacturing method.

[Conventional technology]

Conventionally, various plastic materials, such as polymethyl methacrylate, have been used as ophthalmic materials such as contact lenses and intraocular lenses. However, conventional ophthalmic materials have low oxygen permeability, and dirt components in tear fluid and intraocular fluid tend to stick to them, making it difficult to wear them for long periods of time when used as contact lenses, for example. there were.

Under these circumstances, a high water content soft contact lens was developed that is made mainly of poIJ (N-vinyl-2-pyrrolidone) and can be worn for long periods of time. Due to their nature, they have low mechanical strength, and due to contamination due to water content, they must be sterilized by boiling before being used as contact lenses.
The problem was that it was extremely complicated to handle.

Furthermore, in recent years, a polymer material made by copolymerizing siloxanyl mono(meth)acrylate and fluoro(meth)acrylate has been proposed as an ophthalmic material that overcomes these drawbacks.

[Problem to be solved by the invention]

However, the properties of the above-mentioned polymer materials vary greatly depending on the copolymerization ratio of siloxanyl mono (meth)acrylate and fluoro(meth)acrylate, and oxygen permeability improves as the copolymerization ratio of siloxanyl mono (meth)acrylate increases. However, the adsorption or adhesion of dirt components becomes significant, and the material becomes too brittle and soft.Conversely, increasing the copolymerization ratio of fluoro(meth)acrylate (which makes it difficult for dirt components to adsorb or stick to it, but increases the There was a problem that the transmittance decreased.

Therefore, an object of the present invention is to solve the above-mentioned problems and to provide a material that has high oxygen permeability, does not cause stains due to adsorption or fixation of dirt components in lacrimal fluid and intraocular fluid, and has excellent processability. An object of the present invention is to provide a method for producing an oxygen-permeable polymer material that is suitably used as an ophthalmic material such as a contact lens or an intraocular lens.

[Means to solve the problem]

The present invention is based on the following general formula (1) % formula % [wherein ^1 and ^2 may be the same or different and represent an unsaturated polymerizable group, xl, x2 and x3 are They may be the same or different and represent a divalent hydrocarbon group having 1 to 4 carbon atoms, preferably 2 to 3 carbon atoms, R1, R2,
R3, R4, R5, R6, R'k R'lt, alkyl group which may be the same or different and may be substituted with a fluorine atom, phenyl group, vinyl group, R1+ ■ Hydrogen atom l;! Group -(OSi), -X'-B' (
cocote, fil1噸 and R12 may be the same or different, an alkyl group optionally substituted with a fluorine atom, a phenyl group,
represents a vinyl group or a hydrogen atom, B1 represents an unsaturated polymerizable group or a hydrogen atom, x5 represents a divalent hydrocarbon group having 1 to 10 carbon atoms, preferably 2 to 3 carbon atoms, y represents 0 to 20,
Preferably the number is from 1 to 10. ), R9 and R1 may be the same or different and represent a hydrogen atom, a fluorine atom or a fluoroalkyl group, 1 and W are each O or 1, n and t are each 0 to 20,
Preferably 1-10, q and r each 0-20,
Preferably, the number is O to 10, and q+r≧1. This R'R' group -3lO- and/or group -3iO- in the formula
When a plurality of R2R' exists, each group may be the same or different. ] Provides a method for producing an oxygen-permeable polymer material, which is characterized by polymerizing or copolymerizing one or more polymerizable monomers represented by the following.

In the present invention, examples of the alkyl group in general formula (I) include methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, t-butyl group, and pentyl group. , i-pentyl group, hexyl group, heptyl group, octyl group, 2-ethylhexyl group, nonyl group, decyl group, dodecyl group, undecyl group, etc. Examples of the fluoroalkyl group include trifluoromethyl group. , trifluoroethyl group, trifluoropropyl group, pentafluorobutyl group, heptafluoropentyl group, nonafluorohexyl group, and the like.

Further, examples of the divalent hydrocarbon group in general formula (I) include a methylene group, ethylene group, and propylene group, and examples of the unsaturated polymerizable group include a vinyl group, CH, and ═C
Fluoro (meth)acryloxy group represented by (R)COD- (wherein R represents a hydrogen atom, a fluorine atom, a methyl group or a fluoromethyl group), CH2=CHCON
Acrylamide group represented by H-, CH2=CHC6)
A styryl group represented by 14-, C)1. =C(CN)-
Acrylonitrile group represented by CH,=C(CN)
Examples include a 2-cyanoacryloxy group represented by COO-.

Polymerizable monomer (1) in the present invention (hereinafter referred to as monomer (A)
)) The following can be exemplified.

CH, C)i3CH.

l II CL=C-[:O-(CL) --(SIO) 4-5
l-(C)I2) 2- (CF2) 2- (['
H-) -0CH,CH.

CH3CH,C)I.

II 1 -5i-(Sin)ji(C)12) 5-QC-C=C
HCH3[:H30 CH3CL CH.

C11, CH, CH.

II 1 -3 i-(S iO) 4- (C)I-) 5-O
C-C=CH-CH, CH, O CH, CH, CH.

CH, CH, CH.

CL　　　　　　　　　CL　　C)! .

- (CH-) 2-3i-(S in) --(Ct
12) --OCt(2CHCf12-DC-C=CH
-+1 111 CH,CH,OHO CF, CH,C)l.

CHs=C-CD (CL)3-(Sin)-3i-(
CL)2(CF2)2(CL)z-0C1l,
CH3 -3i-(Sin) 4-(C)I-) --DC-C
=CH.

CHs CL 0 C) 13 C11, CH3CHs1
1 1 lCH2=
C-CD-(C)I2) --(S in) 4-31
-CL-(CF-)--C)l--31-0CH3C
L CH3CH, CH3 -(S+0) --(C)12) 3-DC-C=CH
2C11,0 C)13C)1. C) I, C)
l.

l II ICH=
=C-CO(CHa)s-(S10)--3l-C)I
2-(CFz)4-CH2-9l-D C
)1. CH,C)I.

CH3CH3 C)1. CH, CH3 1ll CH2=C-CD-(C)l-)-(S 1n)-3
i-(C)l-) 2-(CF2) s-(C)
+2) -0CH,CH.

CHs CHs CLl 1
1-3i-(Sin) ,-(CH,) 5-QC-C=
CH2CH, CH, O CH3CH, CH3C1 (.

CHz=C-CD-(CH2) --(S 1o)4-
31-c) I2- (CF2)-CL-S 1-1
1 + 1 10
C) I3Cl(,C)13CH3C'H3 -(Sin)di(CH2) 3-DC-C=C)I2C
The I'+3 0 monomer (A) can be polymerized or copolymerized alone or in combination of two or more.

In addition, in the present invention, a vinyl monomer (hereinafter referred to as monomer (B)) represented by the following general formula (n) or general formula (III) is used together with the monomer (^). Can be polymerized. General formula % formula % [where ^3 is the same as ^1, I6 is the same as I5, R13, R14, Ras and R15l! R',
R2, R'', R4, R5, R6, R7 and R'', Z is a group -(O3+), X@-83 (wherein R
I9 and ft20 are R11 and Rh.

and R12, R3 is the same as 8', and I
6 is similar to I5, and U is similar to y. ) or an alkyl group optionally substituted with a fluorine atom,
k represents an integer of 0 to 100, preferably 1 to 10. ] A siloxane-based polymerizable monomer represented by the general formula ([) % formula %) (wherein, Yl represents a hydrogen atom, a fluorine atom, a methyl group or a fluoromethyl group, and I2 represents the general formula (I). 1 to 20 carbon atoms, preferably 1 to 1 as exemplified in the description
0 fluoroalkyl group. ) fluoro(meth)acrylate.

By copolymerizing these monomers (B), it is possible to further improve the oxygen permeability of the resulting oxygen permeable polymer material, increase its mechanical strength, or reduce the adsorption or adhesion of dirt components. can be improved.

Here, among the monomers (B) used, general formula (I[
) Examples include the following: Pentamethyldisiloxanyl methyl methacrylate, Pentamethyldisiloxanyl methyl acrylate,
pentamethyldisiloxanylpropyl methacrylate,
Pentamethyldisiloxanylpropyl T acrylate, methylbis(trimethylsiloxy)silylpropyl methacrylate, methylbis(trimethylsiloxy)silylpropyl acrylate, tris(trimethylsiloxy)silylpropyl methacrylate), ) IJX(trimethylsiloxy)silylpropyl acrylate, Methylbis(trimethylsiloxy)silylpropylglycerol methacrylate, Methylbis(trimethylsiloxy)silylpropylglycerol acrylate, Tris(trimethylsiloxy)silylpropylglycerol methacrylate, Tris(trimethylsiloxy)silylpropylglycerol acrylate, Mono(methylbis(trimethylsiloxy)siloxy)bis (trimethylsiloxy)silylpropylglycerol methacrylate, chino (methylbis(trimethylsiloxy)siloxy)bis(trimethylsiloxy)silylpropylglycerol acrylate, trimethylsilylethyltetramethyldisiloxanylprobylglycerol methacrylate, trimethylsilylethyltetramethyldisiloxanylbro Siloxanyl mono (meth) such as bilglycerol acrylate
Acrylate; (3,3,3-trifluoropropyldimethylsiloxy)bis(trimethylsiloxy)silylmethylmethacrylate), (3,3,3-trifluoropropyldimethylsiloxy)bis(trimethylsiloxy)
Silyl methyl acrylate, (3,3,4,4,5,5
,5-heptafluoropentyldimethylsiloxy) (
Methylbis(trimethylsiloxy)siloxy)trimethylsiloxysilylpropyl methacrylate, (3,3,
4,4,5,5,5-heptafluoropentyldimethylsiloxy) (methylbis(trimethylsiloxy)siloxy)trimethylsiloxysilylprobyl acrylate, (3,3,4,4°5,5.5-heptafluoropentyl fluorosiloxanyl mono(meth)acrylates such as dimethylsiloxy)(pentamethyldisiloxanyloxy)trimethylsiloxysilyl methacrylate;
Margin CF below.

Siloxanyl di(meth)acrylate represented by etc.

Among the monomers (B), those represented by general formula (III) include, for example, the following.

2.2.2-) Lifluoroethyl methacrylate, 2.
2.2-trifluoroethyl acrylate, 2,2゜2
-trifluoroethyl-α-fluoroacrylate,
2.2.2-) Lifluoroethyl-α-trifluoromethyl methacrylate, 2.2,3.3-tetrafluoropropyl methacrylate), 2.2.3.3-tetrafluoropropyl acrylate, 2.2 .3.3.3-pentafluoropropyl methacrylate), 2.2°3, 3.
3-pentafluoropropyl acrylate, 2, 2.2
．． 2′, 2°, 2°-hexafluoroisopropyl methacrylate, 2.2.2.2°, 2°, 2″-hexafluoroisopropyl acrylate, 2.2.3.4
．． 4.4-hexafluorobutyl methacrylate, 2.
2.3.4.4.4 = Hexafluorobutyl acrylate
), 2.2.3', 3°4, 4.5.5-octafluoropentyl methacrylate, 2.2.3.3.4.
4.5.5-octafluoropentyl acrylate, 2
．． 2.3.3.4.4.5.5.6.6.7.7-dodecafluorohebutyl methacrylate, 2.2.3.3.
4°4, 5.5.6.6.7.7-dodecafluorohebutyl acrylate, 2.2.3.3.4.4.5.5.
6.6.7.7.8.8.9.9-hexadecafluorononyl methacrylate, 2.2.3°3, 4.4.5.
5.6.6.7.7.8.8.9.9-hexadecafluorononyl acrylate, : ], 3.4.4.5.
s, 6.6.7.7.8°8.8-) Ridecafluorooctyl methacrylate, 3.3,4,4.5,5,6
, 6,7,7,8,8.8-) Ridecafluorooctyl acrylate, 2.2,3.3-tetrafluoro-1
-Methylpropyl methacrylate, 2,2,3°3-tetrafluoro-1-methylpropyl acrylate, 2.
2.3.3-tetrafluoro-1,1-dimethylpropyl methacrylate, 2.2.3.3-tetrafluoro-
1,1-dimethylpropyl acrylate, 2, 2.3.
3.4.4.5.5-dimethylpentyl methacrylate, 2.2.3.3.4.4.
5.5-fluoro(meth)acrylates such as 1,1-dimethylpentyl acrylate.

Among these monomers (B), those particularly preferably used in the present invention are pentamethyldisiloxanylmethyl methacrylate, pentamethyldisiloxanylpropyl methacrylate, methylbis(trimethylsiloxy)silylpropyl methacrylate, Siloxanyl mono(meth)acrylates such as tris(trimethylsiloxy)silylpropyl methacrylate; (3,3,3-)lifluoropropyldimethylsiloxy)bis(trimethylsiloxy)silylmethyl methacrylate, (3,3,4
゜4,5.5.5-heptafluoropentyldimethylsiloxy) (methylbis(trimethylsiloxy)siloxy)trimethylsiloxysilylpropyl methacrylate, (3,3,4,4,5,5,5-heptafluoropentyldimethyl siloxy)(pentamethyldisiloxanyloxy)trimethylsiloxysilyl methacrylate and 2.2.2-)lifluoroethyl methacrylate,
2.2.2-) Lifluoroethyl-α-fluoroacrylate, 2.2.2-Trifluoroethyl-α-trifluoromethyl methacrylate, 2.2.3.3-tetrafluoropropyl methacrylate, 2.2. 3.3.3
-pentafluoropropyl methacrylate, 2.2.2
．． 2', 2', 2'-hexafluoroisopropyl methacrylate, 2.2.3.4.4.4-hexafluorobutyl methacrylate, 2.2.3°3, 4.
4.5.5-octafluoropentyl methacrylate,
2.2.3.3.4.4.5.5.6.6.7.7-Dodecafluoro Butyl methacrylate, 3.3.4
．． 4.5.5.6.6.7゜7, El, 8.8-) Ridecafluorooctyl methacrylate, 2.2.3.3-
tetrafluoro-1-methylpropyl methacrylate,
2,2,3.3-tetrafluoro-1,1-dimethylpropyl methacrylate, 2°2, 3.3.4.4.5.
Fluoro(meth)acrylates such as 5-octafluoro-1,1-dimethylpentyl methacrylate.

These monomers (B) can be copolymerized with monomer (A) alone or in combination of two or more.

Here, the copolymerization ratio of monomer (A) and monomer (B) is usually 10 to 100% by weight for monomer (^) and 0 to 90% by weight for monomer (B). Yes, preferably monomer (^
) is 20 to 90% by weight, monomer (B) is 10 to 80% by weight, particularly preferably monomer (A) is 30 to 80% by weight,
Monomer (B) is 20 to 70% by weight.

Furthermore, in the production method of the present invention, in addition to the monomer (^) and monomer (B) mentioned above, other monomers may be copolymerized within a range that does not impair the effects of the present invention. I can do it.

Such other monomers include ethylene glycol dimethacrylate, ethylene glycol diacrylate,
diethylene glycol dimethacrylate, diethylene glycol diacrylate, triethylene glycol dimethacrylate, triethylene glycol diacrylate, tetraethylene glycol dimethacrylate, tetraethylene glycol diacrylate, propylene glycol dimethacrylate, propylene glycol diacrylate), 1,4-butanediol Dimethacrylate, 1
, 4-butanediol diacrylate, neopentyl glycol dimethacrylate, neopentyl glycol diacrylate, trimethylolpropane trimethacrylate, trimethylolpropane) IJ acrylate.

These polyfunctional monomers increase the hardness of the resulting material,
It is used to improve workability such as machinability and polishability, and its copolymerization ratio is usually 30% by weight or less, preferably 20% by weight or less. Copolymerization ratio is 30
If it exceeds % by weight, the resulting material becomes brittle and has low oxygen permeability.

Furthermore, an alkyl mono(meth)acrylate may be copolymerized to improve the strength, processability, etc. of the resulting material.

These alkyl (meth)acrylates include methyl methacrylate, methyl acrylate, ethyl methacrylate, ethyl acrylate, isopropyl methacrylate, isopropyl acrylate, butyl methacrylate, butyl acrylate, tert-butyl methacrylate, tert-butyl acrylate, cyclohexyl methacrylate, and cyclohexyl methacrylate. Mention may be made of alkyl (meth)acrylates such as xyl acrylate, benzyl methacrylate, benzyl acrylate, inbornyl methacrylate, and isobornyl acrylate.

The copolymerization ratio of these alkyl mono(meth)acrylates is usually 50% by weight or less, preferably 40% by weight or less, in order not to impair the oxygen permeability of the resulting material.

In addition, in order to develop hydrophilicity on the surface of the obtained material,
(meth)acrylic acid, N-vinyl-2-pyrrolidone, 2
- Hydrophilic monomers such as hydroxyethyl methacrylate can also be copolymerized.

If the copolymerization ratio of these hydrophilic monomers is increased, the oxygen permeability of the resulting material will be impaired, so the copolymerization ratio is usually 20% by weight or less, preferably 15% by weight or less.

The polymerization or copolymerization in the present invention can be carried out by an ordinary radical polymerization reaction, for example, a method in which the temperature is raised stepwise in the presence of a thermal polymerization initiator such as benzoyl peroxide or azobisisobutyronitrile. Alternatively, polymerization can be carried out by irradiating ultraviolet rays in the presence of a photopolymerization initiator such as benzoin, benzophenone, or Michler's ketone. The thermal polymerization initiator or photopolymerization initiator is generally used in an amount of 0.01 to 5 parts by weight per 100 parts by weight of the monomer mixture.

In addition, when the material obtained by the present invention is used for applications that require compatibility with lachrymal fluid and intraocular fluid, such as contact lenses and intraocular lenses, the material can be processed into the shape of contact lenses and intraocular lenses. After that, hydrophilicity is imparted to the surface by further performing alkali treatment, plasma treatment with oxygen, nitrogen, etc., plasma polymerization with a compound containing a hydrophilic group, or surface treatment by vapor deposition of inorganic oxide, sputtering, or ion blasting. can do.

〔Example〕

The present invention will be explained below with reference to Examples and Comparative Examples.
The present invention is not limited to these.

In addition, the evaluation criteria for workability and the test methods of various tests in the following Examples and Comparative Examples are as follows.

■Evaluation criteria for workability Machinability A: The cut surface is glossy B: The cut surface is glossy but slightly opaque C: The cut surface is rough and white Abrasiveness A: The polished surface has good gloss B: C: Polishing unevenness occurs C: Polished surface becomes rough and white ■ Test method for oxygen permeability coefficient Using the obtained contact lens, use Rika Seiki Kogyo Seikaken type film oxygen permeability meter, 35°C 0.9% physiological Measured in saline.

(2) Test method for visible light transmittance Using the obtained disc, transmittance at 500 to 600 nm was measured using a double beam spectrophotometer model 200-20 manufactured by Hitachi, Ltd. (2).

■Stain resistance test method Using the obtained disc, immerse it in a dirt solution for 30 days, then wash it with a contact lens cleaner (@Rifky Contact Ref 1, Always Cleaner) to remove dirt that adheres to the surface. The visible light transmittance before immersion was reduced to 1.
It was expressed as the rate of change in visible light transmittance when it was set to 00.

The soil solution is a mixed solution consisting of 0.1 parts by weight of egg albumin, 0.1 parts by weight of egg white lysozyme, 1.1 parts by weight of antemortem mucosal mucin, 0.1 parts by weight of egg yolk lecithin, and 100 parts by weight of purified water. The solution was used and replaced with fresh soil solution every 2-3 days.

Example 1 Fluorosiloxanyl dimethacrylate 4 represented by the following formula: % formula %)
0 parts by weight, 20 parts by weight of tris(trimethylsiloxy)silylpropyl methacrylate, 20 parts by weight of 2.2.2-trifluoroethyl methacrylate, 15 parts by weight of methyl methacrylate, 5 parts by weight of ethylene glycol dimethacrylate, and benzoinmethyl as a polymerization initiator. 0.1 part by weight of ether was thoroughly mixed at room temperature, this mixed solution was poured into a polyethylene polymerization container, and copolymerized by irradiating ultraviolet rays at room temperature in a nitrogen atmosphere for 16 hours.

After the copolymerization, the obtained bulk copolymer was cut and polished to form a contact lens and a disk with a thickness of 0.2 mm and a diameter of 150 mm to evaluate processability, and then various tests were conducted. The results are shown in Table-1.

Example 2 Fluorosiloxanyl dimethacrylate 3 represented by the following formula: % formula %)
5 parts by weight, 2.2.2.2°, 2°, 2”-30 parts by weight of hexafluoroisopropyl methacrylate, 25 parts by weight of methyl methacrylate, 5 parts by weight of methacrylic acid, 5 parts by weight of ethylene glycol dimethacrylate, and a polymerization initiator. 0.1 part by weight of benzoin methyl ether was thoroughly mixed at room temperature, and this mixed solution was poured into a polyethylene polymerization container and copolymerized by irradiating ultraviolet rays at room temperature in a nitrogen atmosphere for 16 hours.

After copolymerization, the obtained bulk copolymer is cut and polished to form contact lenses with a thickness of 0.2 mo+ and a diameter of 150 mm.
Workability was evaluated by forming a No. 111 disk, and then various tests were conducted. The results are shown in Table-1.

Comparative Example 1 35 parts by weight of tris(trimethylsiloxy)silylpropyl methacrylate R12,2,2-) 45 parts by weight of trifluoroethyl methacrylate, 15 parts by weight of methyl methacrylate, 5 parts by weight of ethylene glycol dimethacrylate, and 0 parts by weight of benzoin methyl ether as a polymerization initiator. .1
Parts by weight were thoroughly mixed at room temperature, and the mixed solution was poured into a polyethylene polymerization container and copolymerized by irradiating ultraviolet rays at room temperature in a nitrogen atmosphere for 16 hours.

After copolymerization, the resulting bulk copolymer was cut and polished to form a contact lens and a disk with a thickness of 0.2 mm and a diameter of 15 mm to evaluate workability, and then various tests were conducted. The results are shown in Table-1.

The following margin [Effects of the Invention] The oxygen-permeable polymer material produced by the present invention has extremely high oxygen permeability and is free from dirt components in concentrated liquids and intraocular fluids and dirt caused by various usage environments. It has an excellent feature of being difficult to attract or stick to, and also has good machinability such as cutting and polishing properties. Therefore, the oxygen permeable polymer material produced according to the present invention can be used for contact lenses,
Suitable for use as ophthalmic materials such as intraocular lenses.

that's all Applicant: Japan Synthetic Rubber Co., Ltd. I-■3 Neeko Patent attorney Shun Nakajima, -1 t-ゝ-1- −−−′

Claims (1)

[Claims] 1. The following general formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) [In the formula, A^1 and A^2 may be the same or different. X1, X^2 and X^3 may be the same or different and have 1 to 1 carbon atoms.
4 represents a divalent hydrocarbon group, R^1, R^2, R^3
, R^4, R^5, R^6, R^7 and R^8 may be the same or different, and are an alkyl group, a phenyl group, a vinyl group, which may be substituted with a fluorine atom, Hydrogen atoms or groups ▲ Numerical formulas, chemical formulas, tables, etc. group, phenyl group, vinyl group or hydrogen atom, B^
1 represents an unsaturated polymerizable group or a hydrogen atom, X^5 represents a divalent hydrocarbon group having 1 to 10 carbon atoms, and y represents 0 to 20
Indicates the number of ), R^9 and R^1^0 may be the same or different and represent a hydrogen atom, a fluorine atom or a fluoroalkyl group, and l and w are each 0
or 1, n and t are respectively 0-20, q and r
each represents a number from 0 to 20, and q+r≧1. Here, if there are multiple groups ▲There are mathematical formulas, chemical formulas, tables, etc.▼ and/or groups ▲There are mathematical formulas, chemical formulas, tables, etc.▼ in the formula, each group may be the same but different. Good too. ] A method for producing an oxygen-permeable polymer material, which comprises polymerizing or copolymerizing one or more polymerizable monomers represented by: