JPH085969A - Material for medical use - Google Patents

Abstract

PURPOSE:To provide such a material for medical use that gives excellent feeling of fitting, has excellent mechanical characteristics and durability, is hardly contaminated, and that even when contamination deposits, it can be easily removed. CONSTITUTION:The feature of this material for medical use is a polymerized compd. expressed by formula A-Y-X-Y-B [I]. In formula [I], X is an unsatd. dicarboxylic acid group, Y is O or NR1, wherein R1 is a hydrogen atom or a group selected from alkyl groups, hydroxyalkyl groups, or aryl groups, A and B are same or different groups and at least one of A and B is expressed by formula-(CR3R4)n-(CR5R6)m-N(R7)-C(R8)O [II]. When only one of A and B is the group expressed by formula [II], the other of A and B is a hydrogen atom or a group selected from alkyl groups, hydroxyalkyl groups, halogenated alkyl groups, aryl groups, halogenated aryl groups, -(CH2CH2O)p-H, and -CH, CH2(OH)CH2-(O)r-R2.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a medical material, particularly an intraocular lens and a contact lens.

[0002]

BACKGROUND OF THE INVENTION It is well known that medical devices such as artificial organs, hemodialysis membranes, various catheters, intraocular lenses and contact lenses are made of polymeric materials. For example, an intraocular lens and a contact lens are produced using a polymer of polymethylmethacrylate (PMMA) and various methacrylic acid ester monomers. This PMM
A methacrylic acid ester-based polymer such as A has excellent optical properties (transparency) and is highly durable, but has poor water wettability.
Oxygen permeability is low, so contact lenses of methacrylic acid ester polymers such as PMMA have a bad feeling of wearing,
Especially, there is a problem that it is difficult to wear for a long time.

In order to improve the oxygen permeability of the methacrylic acid ester-based polymer such as PMMA, a silicone-methacrylate polymer having a siloxane bond introduced into the methacrylic acid ester molecule (Japanese Patent Publication No. 52-33502),
Oxygen permeable polymers mainly composed of cellulose acetate butyrate and methacrylic polymers containing fluorine (Japanese Patent Laid-Open No. 57-51705).
JP-A-61-11308) and the like have been proposed. However, although these polymers have improved oxygen permeability as compared with methacrylic acid ester-based polymers such as PMMA,
Addition polymerization of a small amount of a hydrophilic monomer is considered because it is still insufficient and the water wettability is not satisfactory. However, in this case, depending on the proportion of the hydrophilic monomer, the polymer obtained has new drawbacks such as a new problem of white turbidity of the material due to phase separation.
Further, the performance such as stain resistance is not satisfactory.

On the other hand, a contact lens is manufactured by using a water-containing material containing 2-hydroxyethyl methacrylate (2-HEMA) as a main component. Although this water-containing material is rich in water wettability and has a good wearing feeling, it is not satisfactory in oxygen permeability, and therefore, this is not enough for continuous wearing for a long time. It is also proposed to produce a contact lens from a highly water-containing material copolymerized with N-vinyl lactam and an alkyl methacrylic acid ester (Japanese Patent Publication No. 57-42850 and Japanese Patent Publication No. 57-428).
No. 51). This material excels in water wettability and oxygen permeability, so the contact lens made of this material can be worn continuously for a long time, but when it is sterilized by boiling, it deforms or discolors. In addition, it has poor durability and is easily contaminated by proteins, fats, mucins, bacteria and fungi contained in tear components.

As a means for solving these drawbacks, copolymerization with a fluorine-containing monomer has been proposed (JP-A-57-2111).
No. 19, JP-A-63-30820), however, new defects such as a decrease in water content, flexibility and cloudiness of the copolymer were found. Recently, in order to solve these drawbacks, addition copolymerization of a fluorine-containing monomer having an OH group at the side chain portion or at the terminal has been proposed. It was not possible to fully overcome the shortcomings of.

[0006]

DISCLOSURE OF THE INVENTION It is an object of the present invention to provide a medical material which is excellent in wearing feeling, has excellent mechanical properties and durability, is hard to be soiled, and is easily removed even if soiled. is there. The object of the present invention is achieved by a medical material characterized by being polymerized using a compound represented by the following general formula [I].

General formula [I] A-Y-X-Y-B [In the formula [I], X is an unsaturated dicarboxylic acid group, Y is O or NR ₁ (provided that Y is the same or different. May be). R ₁ is a hydrogen atom, or a chain-like (straight or branched chain) alkyl group having 1 to 8 carbon atoms, a chain-like (straight chain or branched chain) hydroxyalkyl group having 1 to 8 carbon atoms, And a group selected from the group of aryl groups.

A and B are the same or different groups,
At least one group of A and B is represented by the general formula [II]. When only one of A and B is represented by the general formula [II], the other of A and B is a hydrogen atom or a carbon number of 1 to 1.
20 linear (branched or branched) alkyl groups,
C4-C12 cyclic alkyl group, C1-C8 chain (straight or branched) hydroxyalkyl group, C1-C15 chain (straight or branched)
Halogenated alkyl group, cyclic halogenated alkyl group having 4 to 12 carbon atoms, aryl group, halogenated aryl group,-(CH ₂ CH ₂ O) pH (p is an integer of 2 to 10), -CH ₂ CH
₂ (OH) CH _2- (O) rR ₂ (R ₂ is a linear (branched or branched) halogenated alkyl group having 1 to 15 carbon atoms, and r is 0)
Or a group selected from the group of 1). ] Formula - in (II) _{(CR 3 R 4) n- (} CR 5 R 6) mN (R 7) -C (R 8) 0 [Formula _{(II), R 3, R 4, R} 5, R ₆ , R ₇ , R ₈
(R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , and R ₈ may be the same or different) is a hydrogen atom, or 1 to
20 linear (branched or branched) alkyl groups,
A cyclic alkyl group having 4 to 12 carbon atoms, a chain (straight or branched) halogenated alkyl group having 1 to 15 carbon atoms, a cyclic halogenated alkyl group having 4 to 12 carbon atoms, an aryl group, A group selected from the group of aryl halide groups.

Further, R ₇ may be a linear (branched or branched) hydroxyalkyl group having 1 to 8 carbon atoms. n and m are integers of 0 to 6] In particular, a medical material characterized by being obtained by copolymerizing a compound represented by the general formula [I] and a compound copolymerizable therewith To be achieved.

That is, one or more compounds represented by the general formula [I]: about 1 to 9 are copolymerizable compounds.
The copolymer is preferably composed of a ratio (polymerization ratio) of 9:99 to 1. Even more preferably, about 5
It is a copolymer composed of a ratio (polymerization ratio) of 95:95 to 5. In addition, since the compound represented by the general formula [I] is a di-substituted product, by further substituting one or both of the substituents with a fluorine-containing substituent or the like, further improvement in stain resistance is observed, Moreover, the water repellency of fluorine is suppressed, and a medical material excellent in water wettability can be obtained.

The present invention will be described in detail below. The compound of the general formula [I] used in the present invention is, for example, itaconic acid type compound, itaconic acid, itaconic anhydride, itaconic acid dichloride, mono-substituted itaconic acid, mono-substituted itaconic acid chloride and alcohols or amines. It can be synthesized by a method such as a reaction with a compound.
Further, fumaric acid and maleic acid type compounds can be similarly obtained.

R ₁ in the general formula [I] is a hydrogen atom, for example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n- Pentyl group, isopentyl group, neopentyl group, tert-pentyl group, 2-methylbutyl group, n-hexyl group, isohexyl group, 1-
Methylpentyl group, 2-methylpentyl group, 3-methylpentyl group, 2,2-dimethylbutyl group, 2,3-dimethylbutyl group, n-heptyl group, 2-methylhexyl group, 5-methylhexyl group, n -Octyl group, 2-ethylhexyl group, 2,2,4-trimethylpentyl group, which is a linear or branched alkyl group having 1 to 8 carbon atoms (among these, preferred are methyl group, ethyl group, n group). −
Propyl group, isopropyl group, n-butyl group, isobutyl group), for example, hydroxymethyl group, 2-hydroxyethyl group, 2-hydroxypropyl group, 3-hydroxypropyl group, 2-hydroxybutyl group, 4-hydroxybutyl group, 3-hydroxy-2-methylpropyl group, 2-
A straight-chain or branched-chain hydroxyalkyl group having 1 to 8 carbon atoms such as hydroxyhexyl group and 2-hydroxyoctyl group (among others, preferred are hydroxymethyl group, 2-hydroxyethyl group, and 2-hydroxypropyl group). , 2-hydroxybutyl group), for example, a phenyl group,
6 to 30 carbon atoms having free valences such as tolyl group, xylyl group, cumenyl group, mesityl group, biphenylyl group, naphthyl group, anthryl group and phenanthryl group in the carbocycle
Aryl groups such as benzyl group, phenethyl group, diphenylmethyl group, and triphenylmethyl group are selected from the group of aryl groups having 7 to 30 carbon atoms in the side chain.

R ₂ is, for example, a perfluoromethyl group,
2,2,2-trifluoroethyl group, 1,1,2,2-
Tetrafluoroethyl group, 2,2,3,3-tetrafluoropropyl group, perfluoropropyl group, perfluorobutyl group, perfluoro-3- (methyl) butyl group,
Perfluorohexyl group, perfluorooctyl group, perfluoro-8- (methyl) decyl group, perfluoro-
A halogenated alkyl group having 1 to 15 carbon atoms in which a part or all of hydrogen atoms in a linear or branched alkyl group such as a 12- (methyl) tetradecyl group is substituted with a halogen atom (among others, a preferable one is , A halogenated alkyl group in which a part or all of the hydrogen atoms of a linear or branched alkyl group having 1 to 8 carbon atoms is substituted with a halogen atom).

R ₃ , R ₄ in the general formula [II],
R ₅ , R ₆ , R ₇ and R ₈ are hydrogen atoms such as methyl group,
Ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, 2-methylbutyl group, n
-Hexyl group, isohexyl group, 1-methylpentyl group, 2-methylpentyl group, 3-methylpentyl group,
2,2-dimethylbutyl group, 2,3-dimethylbutyl group, n-heptyl group, 2-methylhexyl group, 5-methylhexyl group, n-octyl group, 2-ethylhexyl group, 2,2,4-trimethyl Pentyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridodecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n- A straight-chain or branched-chain alkyl group having 1 to 20 carbon atoms such as octadecyl group, n-nonadecyl group, and icosanyl group (among these, preferred are methyl group, ethyl group, n-propyl group, isopropyl group, n -Butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, -Hexyl group), for example, cyclopropylmethyl group, cyclobutyl group, cyclopentyl group, methylcyclobutyl group, cyclohexyl group, dimethylcyclobutyl group, methylcyclopentyl group, cycloheptyl group, methylcyclohexyl group, dimethylcyclopentyl group, trimethylcyclobutyl group. , A cyclooctyl group, a cyclononyl group, a cyclodecyl group, a cyclododecyl group, and a cyclic alkyl group having a carbon number of 4 to 12 (among others, a 5- or 6-membered cyclic alkyl group is preferable), for example, perfluoro. Methyl group, 2,2,2-trifluoroethyl group, 2,2,3,3-tetrafluoropropyl group, 2,2,3,3,3-pentafluoropropyl group, hexafluoroisopropyl group, perfluoro-
3- (methyl) butyl group, perfluorohexyl group, 2
-(Perfluorohexyl) ethyl group, perfluoro-
7- (methyl) octyl group, 2- (perfluorodecyl) ethyl group, 2- (perfluoro-11- (methyl)
Halogenated alkyl groups having 1 to 15 carbon atoms in which a part or all of hydrogen atoms in a linear or branched alkyl group such as a dodecyl) ethyl group is substituted with a halogen atom (among others, a carbon number is preferably 1-8 linear or branched alkyl groups, some or all of the hydrogen atoms of which are substituted with halogen atoms, halogenated alkyl groups),
For example, monofluorocyclobutyl group, perfluorocyclopentyl group, pentafluorocyclopentyl group, difluoropentyl group, perfluorocyclohexyl group, hexafluorocyclohexyl group, trifluorocyclohexyl group, perfluorocyclooctyl group, octafluorocyclooctyl group, tetrafluoro A cyclohalogenated alkyl group having 4 to 12 carbon atoms in which a part or all of hydrogen atoms of a cycloalkyl group such as a cyclooctyl group and a difluorocyclododecyl group are substituted with a halogen atom (among others, a 5-membered one is preferable. A cyclic halogenated alkyl group in which some or all of the hydrogen atoms of a cyclic or 6-membered cyclic alkyl group are replaced with halogen atoms), such as phenyl group, tolyl group, xylyl group, cumenyl group, mesityl group, biphenylyl , Naphthyl group, anthryl group, phenanthryl group, free valence of 6 to 30 carbon atoms in the carbocycle such as benzyl group, phenethyl group, diphenylmethyl group, triphenylmethyl group. Aryl group having 7 to 30 carbon atoms in the chain, for example, perfluorophenyl group, monofluorophenyl group, trifluorophenyl group, pentafluorophenyl group, perfluorotolyl group, monofluorotolyl group, tetrafluorotolyl group, perfluoro A halogenated aryl group having 6 to 30 carbon atoms in which some or all of hydrogen atoms of an aryl group having a free valence such as a xylyl group are substituted with a halogen atom, for example, a monofluorobenzyl group, trifluoro Benzyl group, pentafluorobenzyl group, monofluorophenethyl Some or all of the hydrogen atoms of aryl groups with free valences such as, difluorophenethyl group, trifluorophenethyl group, pentafluorophenethyl group, perfluorodiphenylmethyl group, and perfluorotriphenylmethyl group. Is selected from the group of halogenated aryl groups having 7 to 30 carbon atoms substituted with a halogen atom.

Further, R ₇ is, for example, hydroxymethyl group, 2-hydroxyethyl group, 2-hydroxypropyl group, 3-hydroxypropyl group, 2-hydroxybutyl group, 4-hydroxybutyl group, 3-hydroxy-2- group. A straight-chain or branched hydroxyalkyl group having 1 to 8 carbon atoms such as methylpropyl group, 2-hydroxyhexyl group, and 2-hydroxyoctyl group (among them, preferred are hydroxymethyl group and 2-hydroxyethyl group). ,
2-hydroxypropyl group, 2-hydroxybutyl group)
May be

A chain alkyl group, a cyclic alkyl group, a halogenated alkyl group, an aryl group, a halogenated aryl group, which is mentioned as the other of A and B in the case where only one of A and B has the formula [II], Specific examples of the hydroxyalkyl group (which may be a dihydroxyalkyl group) and the like include those mentioned in the description of the general formula [II].

The compound used in the polymerization together with the compound represented by the general formula [I] in the present invention is, for example, C
Esters of _{1 to} C ₁₁ monohydric or polyhydric alcohols with acrylic acid, methacrylic acid or itaconic acid (including acrylic acid alkoxyalkyl esters, methacrylic acid alkoxyalkyl esters, etc.), straight chain having 1 to 20 fluorine atoms Esters of chain-like or branched-chain fluoroalkyl alcohols or fluoroalkylbenzyl alcohols with acrylic acid, methacrylic acid or itaconic acid, silicon-containing monomers, N-vinyl heterocyclic monomers, crosslinkable polyfunctional monomers, etc. Is mentioned.

Further, a part of acrylic acid ester, methacrylic acid ester, and itaconic acid ester (different from the compound represented by the general formula [I]) can be substituted with similar monomers. Examples of esters of C ₁ -C ₁₁ monohydric or polyhydric alcohols with acrylic acid, methacrylic acid or itaconic acid include methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, n-propyl acrylate and n-propyl methacrylate. , Iso-propyl acrylate, iso-
Propyl methacrylate, n-butyl acrylate, n
-Butyl methacrylate, iso-butyl acrylate, iso-butyl methacrylate, tert-butyl acrylate, tert-butyl methacrylate, pentyl acrylate, pentyl methacrylate, neopentyl acrylate, neopentyl methacrylate, hexyl acrylate, hexyl methacrylate, cyclohexyl acrylate, cyclohexyl methacrylate,
2-ethylhexyl acrylate, 2-ethylhexyl methacrylate, 2-hydroxyethyl acrylate,
2-hydroxyethyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 2,3-dihydroxypropyl acrylate, 2,3-dihydroxypropyl methacrylate, 2
-Acrylic esters and methacrylic acid such as hydroxybutyl acrylate, 2-hydroxybutyl methacrylate, 2-hydroxystyrene acrylate, 2-hydroxystyrene methacrylate, diethylene glycol monoacrylate, diethylene glycol monomethacrylate, triethylene glycol monoacrylate, and triethylene glycol monomethacrylate. Ester, dimethyl itaconate, monomethyl itaconate, diethyl itaconate, monoethyl itaconate, di-n-propyl itaconate, mono-n-propyl itaconate, diisopropyl itaconate, monoisopropyl itaconate, di-n-butyl itaconate, itaconate Mono n-butyl, dipentyl itaconate, monopentyl itaconate, dineopentyl itaconate, itaco Acid Mononeopenchiru, itaconic di n- hexyl, itaconic acid mono-n- hexyl, dicyclohexyl itaconate, itaconic acid monocyclohexyl,
Di-2-ethylhexyl itaconate, mono-2-itaconate
Examples thereof include itaconic acid diesters such as ethylhexyl and itaconic acid monoesters.

Examples of the acrylic acid alkoxyalkyl ester and the methacrylic acid alkoxyalkyl ester include 2-methoxyethyl acrylate, 2-methoxyethyl methacrylate, 2-ethoxyethyl acrylate, 2-ethoxyethyl methacrylate, 2-butoxyethyl acrylate and 2-methoxyethyl acrylate. Butoxyethyl methacrylate, 3-methoxypropyl acrylate, 3-methoxypropyl methacrylate, 3-ethoxypropyl acrylate, 3-ethoxypropyl methacrylate, 2-methoxypropyl acrylate, 2-methoxypropyl methacrylate, 2-ethoxypropyl acrylate, 2
-Acrylic acid alkoxyalkyl esters such as ethoxypropyl methacrylate, phenoxyethyl acrylate, and phenoxyethyl methacrylate, and methacrylic acid alkoxyalkyl esters.

Of course, these esters may be used alone or in combination of two or more. Further, a part of the above ester may be replaced with a monomer similar to these.
For example, phenyl acrylate, phenyl methacrylate, benzyl acrylate, benzyl methacrylate,
Glycidyl acrylate, glycidyl methacrylate,
Tetrahydrofurfuryl acrylate, tetrahydrofurfuryl methacrylate, acrylamide, methacrylamide, N-methylol acrylamide, N-methylol methacrylamide, N-alkyl acrylamide,
N, N-dialkyl acrylamide, N-alkyl methacrylamide, N, N-dialkyl methacrylamide,
Morpholino acrylate, morpholino methacrylate,
Morpholinoethyl acrylate, morpholinoethyl methacrylate, aminoalkyl acrylate, aminoalkyl methacrylate, N-alkylaminoalkyl acrylate, N, N-dialkylaminoalkyl acrylate, N-alkylaminoalkyl methacrylate,
N, N-dialkylaminoalkyl methacrylate, acrylic acid, methacrylic acid, fumaric acid, itaconic acid, maleic acid, maleic acid monoester, maleic acid diester, fumaric acid monoester, fumaric acid diester (represented by the general formula [I] It is different from the one) and so on.

Examples of the esters of a linear or branched fluoroalkyl alcohol or a fluoroalkylbenzyl alcohol having 1 to 20 fluorine atoms with acrylic acid, methacrylic acid or itaconic acid include, for example, 2,2,2- Trifluoroethyl acrylate, 2,
2,2-trifluoroethyl methacrylate, 2,2
3,3-tetrafluoropropyl acrylate, 2,
2,3,3-tetrafluoropropyl methacrylate,
2,2,3,3,4,4,5,5-octafluoropentyl acrylate, 2,2,3,3,4,4,5,5-
Octafluoropentyl methacrylate, 1H, 1H,
2H, 2H-heptadecafluorodecyl acrylate,
1H, 1H, 2H, 2H-heptadecafluorodecyl methacrylate, 1H, 1H-pentadecafluorooctyl acrylate, 1H, 1H-pentadecafluorooctyl methacrylate, 1H, 1H-pentafluoropropyl acrylate, 1H, 1H-pentafluoropropyl Methacrylate, hexafluoroisopropyl acrylate, hexafluoroisopropyl methacrylate,
1H, 1H-hexafluorobutyl acrylate, 1
H, 1H-hexafluorobutyl methacrylate, o-
Acrylic acid fluoroesters and methacrylic acid fluoroesters such as trifluoromethylbenzyl acrylate, o-trifluoromethylbenzyl methacrylate, p-trifluoromethylbenzyl acrylate, and p-trifluoromethylbenzyl methacrylate, bis-2,2,2.
2-trifluoroethyl itaconate, 2,2,2-trifluoroethyl itaconate, bis-2,2,3,3
-Tetrafluoropropyl itaconate, 2,2,3
3-tetrafluoropropyl itaconate, bis-2,
2,3,3,4,4-octafluoropentyl itaconate, 2,2,3,3,4,4-octafluoropentyl itaconate, bis-1H, 1H, 2H, 2H, -heptadecafluorodecyl itakonate Nate, 1H, 1H, 2
H, 2H, -heptadecafluorodecyl itaconate,
Bis-1H, 1H-pentadecafluorooctylitaconate, 1H, 1H-pentadecafluorooctylitaconate, bis-1H, 1H-pentafluoropropylitaconate, 1H, 1H-pentafluoropropylitaconate, bishexafluoroisopropyl Itaconate, hexafluoroisopropyl itaconate, bis-1H, 1H-heptafluorobutyl itaconate, bis-o-trifluoromethylbenzyl itaconate, o
-Trifluoromethylbenzyl itaconate, bis-p
-Itaconic acid difluoroesters such as trifluoromethylbenzyl itaconate and p-trifluoromethylbenzyl itaconate, and itaconic acid monofluoroester. Of course, one kind or two or more kinds may be used.

Organosiloxane or the like is used as the silicon-containing monomer. For example, acryloxyethoxypropyl pentamethyldisiloxane, methacryloxyethoxypropyl pentamethyldisiloxane, acryloxyethoxypropylheptamethyltrisiloxane,
Methacryloxyethoxypropylheptamethyltrisiloxane, acryloxyethoxypropyltris (trimethylsiloxy) silane, methacryloxyethoxypropyltris (trimethylsiloxy) silane, acryloxyethoxypropylphenyltetramethyldisiloxane,
Methacryloxyethoxypropylphenyltetramethyldisiloxane, acryloxyethoxypropyltribenzyldiethyldisiloxane, methacryloxyethoxypropyltribenzyldiethyldisiloxane, acryloxyethoxypropyl n-pentylhexamethyltritosiloxane, methacryloxyethoxypropyl n-pentylhexa Methyltrisiloxane, acryloxyethoxypropyldi-n-propylpentamethyltrisiloxane,
Methacryloxyethoxypropyldi-n-propylpentamethyltrisiloxane, acryloxyethoxypropylphenyloctamethyltetrasiloxane, methacryloxyethoxypropylphenyloctamethyltetrasiloxane, acryloxyethoxypropylisobutyltetramethyldisiloxane, methacryloxyethoxypropylisobutyltetramethyl Disiloxane, acryloxyethoxypropylmethylbis (trimethylsiloxane),
Methacryloxyethoxypropylmethylbis (trimethylsiloxane), acryloxyethoxypropyltris (dimethylcyclohexylsiloxy) silane, methacryloxyethoxypropyltris (dimethylcyclohexylsiloxy) silane, acryloxyethoxypropylpentamethyldisiloxybis (trimethylsiloxy) silane, Methacryloxyethoxypropyl pentamethyldisiloxybis (trimethylsiloxy) silane, acryloxyethoxypropylheptamethylcyclotetrasiloxane, methacryloxyethoxypropylheptamethylcyclotetrasiloxane, acryloxyethoxypropyltetramethyltripropylcyclotetrasiloxane, methacryloxyethoxy Propyl tetramethyl tripropyl cyclotetrasiro Sun, acryloxyethoxypropyl-tris (carboxyethyldimethylsiloxy) silane, methacryloxyethoxypropyl-tris (carboxyethyldimethylsiloxy) silane, 1-acryloxyethoxypropyl-3- (hydroxyethoxypropyl) -1,1,3 , 3- (Tetramethyl) disiloxane, 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- (4,7,10, 13,16-pentaoxyoctadecyl-18-ol) 1,1,3,3
-(Tetramethyl) disiloxane, 1-acryloxyethoxypropyl-3-[(3,6-dioxyoctyl-
8-ol-1-oxycarbonyl) ethyl] -1,
1,3,3- (tetramethyl) disiloxane, 1-methacryloxyethoxypropyl-3-[(3,6-dioxyoctyl-8-ol-1-oxycarbonyl) ethyl] -1,1,3 3- (tetramethyl) disiloxane, 1-acryloxyethoxypropyl-3-[(hydroxyethyloxycarbonyl) propyl] -1,1,
3,3- (Tetramethyl) disiloxane, 1-methacryloxyethoxypropyl-3-[(hydroxyethyloxycarbonyl) propyl] -1,1,3,3- (tetramethyl) disiloxane, 1-acryloxyethoxy Propyl-5-[(dihydroxypropyloxy) propyl] -1,1,3,3,5,5- (hexamethyl) trisiloxane, 1-methacryloxyethoxypropyl-5
-[(Dihydroxypropyloxy) propyl] -1,
1,3,3,5,5- (hexamethyl) trisiloxane, acryloxypropyl-1,1,3,3,3-pentamethyldisiloxane, methacryloxypropyl-1,
1,3,3,3-pentamethyldisiloxane, acryloxypropyl-1,1,3,3,5,5,5-heptamethyltrisiloxane, methacryloxypropyl-1,
1,3,3,5,5,5-heptamethyltrisiloxane, acryloxypropyl-tris (trimethylsiloxy) silane, methacryloxypropyl-tris (trimethylsiloxy) silane, acryloxypropyl-3-phenyl-1,1 , 3,3-tetramethyldisiloxane,
Methacryloxypropyl-3-phenyl-1,1,3,3
3-tetramethyldisiloxane, acryloxypropyl-1,1-diethyl-3,3,3-tribenzyldisiloxane, methacryloxypropyl-1,1-diethyl-
3,3,3-tribenzyldisiloxane, acryloxypropyl-1,1,3,3,5,5-hexamethyl-3
-Pentyltrisiloxane, Methacryloxypropyl-
1,1,3,3,5,5-hexamethyl-3-pentyltrisiloxane, acryloxypropyl-3,3,5,
5,5-pentamethyl-1,1-dipropyltrisiloxane, methacryloxypropyl-3,3,5,5,5-
Pentamethyl-1,1-dipropyltrisiloxane, acryloxypropyl-1,1,3,3,5,5,7,7
-Octamethyl-7-phenyltetrasiloxane, acryloxypropyl-1,1,3,3,5,5,7,7-
Octamethyl-7-phenyltetrasiloxane, acryloxypropyl-3-isobutyl-1,1,3,3-tetramethyldisiloxane, methacryloxypropyl-3
-Isobutyl-1,1,3,3-tetramethyldisiloxane, acryloxypropylmethylbis (trimethylsiloxy) silane, methacryloxypropylmethylbis (trimethylsiloxy) silane, acryloxypropyltris (dimethylcyclohexylsiloxy) silane, methacryl Roxypropyltris (dimethylcyclohexylsiloxy) silane, acryloxypropyl (pentamethyldisiloxy) bis (trimethylsiloxy) silane, methacryloxypropyl (pentamethyldisiloxy) bis (trimethylsiloxy) silane, acryloxypropylheptamethylcyclotetrasiloxane , Methacryloxypropylheptamethylcyclotetrasiloxane, acryloxypropyl-1,3,5,7-tetramethyl-3,
5,7-Tripropylcyclotetrasiloxane, Methacryloxypropyl-1,3,5,7-tetramethyl-
3,5,7-tripropylcyclotetrasiloxane,
(Methyl = 3- (3- (3-3.3-trimethyl-1.
1-bis ((trimethylsilyl) oxy) disiloxanyl) propyl) oxycarbonyl-3-butenate,
(Ethyl = 3- (3- (3 / 3.3-trimethyl-1.
1-bis ((trimethylsilyl) oxy) disiloxanyl) propyl) oxycarbonyl-3-butenate,
(Butyl = 3- (1-ethyl-3 / 3-trimethyl-3-(-1-((trimethylsilyl) oxy) disiloxanyl) propyl) oxycarbonyl-3-butenate,
(Isopropyl = 3- (3- (3.3-trimethyl-1
1-diphenyldisiloxanyl) propyl) oxycarbonyl-3-butenate, (3- (3/3 / 3-trimethyl-1-1-bis ((trimethylsilyl) oxy))
Disiloxanyl) propyl = 3-phenethyloxycarbonyl-3-butenate, (3- (3 / 3.3-trimethyl-1.1.1-bis ((trimethylsilyl) oxy) disiloxanyl) propyl = 3-methoxycarbonyl-3
-Butenate, (propyl = 3- (3- (3.3.5.
5.5-pentamethyl-1.1-diphenyl) propyl) oxycarbonyl-3-butenate, (3- (3.
3,3-Trimethyl-1,1-bis ((trimethylsilyl) oxy) disiloxanyl) propyl = 3- (3-
(3 / 3-Trimethyl-1-1.1-bis ((trimethylsilyl) oxy) disiloxanyl) propyl) oxycarbonyl-3-butenate, (3- (1.3.3.3.3)
-Tetramethyl-1-((trimethylsilyl) oxy)
Disiloxanyl) propyl = 3- (3-1.3.3.3.)
-Tetramethyl-1-((trimethylsilyl) oxy)
Disiloxanyl) propyl) oxycarbonyl-3-butenate, (3- (1.1.3 / 3-tetramethyl-3
-(Phenyldisiloxanyl) propyl = 3- (3-
(1.1 / 3-tetramethyl-3-phenyldisiloxanyl) propyl) oxycarbonyl-3-butenate, methyldi (trimethylsiloxy) silylpropyl glycerol acrylate, methyldi (trimethylsiloxy) silylpropyl glycerol methacrylate, methyldi Examples thereof include (trimethylsiloxy) silylpropyl glycerol ethyl acrylate and methyldi (trimethylsiloxy) silylpropyl glycerol ethyl methacrylate. Of course, one kind or two or more kinds may be used.

Examples of the N-vinyl heterocyclic compound include N-vinyl-2-pyrrolidone, N-vinyl-2-piperidone, N-vinyl-2-caprolactam, N-vinyl-3-methyl-2-pyrrolidone, N-vinyl-3-methyl-2-piperidone, N-vinyl-3-methyl-2-caprolactam, N-vinyl-5-methyl-2-pyrrolidone, N-vinyl-5-methyl-2-piperidone, N- Vinyl-3-ethyl-2-pyrrolidone, N-vinyl-4,
5-dimethyl-2-pyrrolidone, N-vinyl-5,5-
Dimethyl-2-pyrrolidone, N-vinyl-3,3,5-
Trimethyl-2-pyrrolidone, N-vinyl-5-methyl-5-ethyl-2-pyrrolidone, N-vinyl-3,4
5-trimethyl-3-ethyl-2-pyrrolidone, N-vinyl-6-methyl-2-piperidone, N-vinyl-6-
Ethyl-2-piperidone, N-vinyl-3,5-dimethyl-2-piperidone, N-vinyl-4,4-dimethyl-
2-piperidone, N-vinyl-7-methyl-2-caprolactam, N-vinyl-7-ethyl-2-caprolactam, N-vinyl-3,5-dimethyl-2-caprolactam, N-vinyl-4,6- N-vinyllactam such as dimethyl-2-caprolactam, N-vinyl-3,5,7-trimethyl-2-caprolactam, etc., other N-vinylimidazolidone, N-vinylsuccinimide, N-vinyldiglycolylimide, N- Vinyl-3-morpholinone,
N-vinyl-5-methyl-3-morpholinone and the like can be mentioned. Of course, one kind or two or more kinds may be used.

Examples of the crosslinkable polyfunctional monomer include ethylene glycol diacrylate, ethylene glycol dimethacrylate, diethylene glycol diacrylate, diethylene glycol dimethacrylate, triethylene glycol diacrylate, triethylene glycol dimethacrylate, tetraethylene glycol diacrylate, tetraethylene. Glycol dimethacrylate, propylene glycol diacrylate, propylene glycol dimethacrylate, dipropylene glycol diacrylate, dipropylene glycol dimethacrylate, tripropylene glycol diacrylate, tripropylene glycol dimethacrylate, trimethylolpropane triacrylate, trimethylolpropane trimethacrylate Polyfunctional acrylic acid ester, polyfunctional methacrylic acid ester, vinyl acrylate, vinyl methacrylate, divinylbenzene, N, N'-divinylbislactam and other polyfunctional vinyl compounds, allyl acrylate, allyl methacrylate, diallyl itaconate, monoallyl itako Nate, diallyl succinate,
Multifunctional allyl compounds such as diallyl adipate, diallyl phthalate, diallyl isophthalate, diallyl terephthalate, triallyl cyanurate, triallyl isocyanurate, allyloxyethyl acrylate, allyloxyethyl methacrylate, diallyloxyethyl itaconate, monoallyloxy Ethyl itaconate, 3-butenoic acid methacryloyloxyethyl ester, 2-butenoic acid methacryloyloxyethyl ester, pentaerythritol tetra (3-butenate), pentaerythritol tetra (crotonate), 1,3,5-tri ( 3-butenoic acid)
Phenyl ester, 1,3,5-tri (2-butenoic acid) phenyl ester, tri (3-butenoyloxyethyl) isocyanurate, tri (2-butenoyloxyethyl) isocyanurate, [2- (1'-methacryloyloxyethyl) -4-allyl] -N, N-
Tolylene carbamate, 4-allyl-2- (N-methacryloylaminotriyl) -N'-carbamate, 2,
4-diallyl-N, N'-tolylenebiscarbamate,
[2-allyl-4- (1'-methacryloyloxyethyl)]-N, N'-tolylenecarbamate, 2-allyl-4- (N-methacryloylaminotriyl) -N'-
Carbamate, 2,4- (1 ′, 1 ″ -dimethacryloyloxyethyl) -N, N′-tolylene biscarbamate, 1,3,5-triallyl-N, N ′, N ″ -benzenetris Carbamate etc. are mentioned. Of course, one kind or two or more kinds may be used.

The medical material of the present invention (particularly, contact lens material) is prepared by polymerizing the compound represented by the general formula [I],
In particular, it is produced by copolymerizing the compound represented by the general formula [I] with the above-mentioned copolymerizable compound. In particular, a copolymerizable compound for improving the balance of optical characteristics, oxygen permeability, water wettability, anti-oxidation resistance, durability, stain resistance, mechanical characteristics, shape stability, etc. of contact lenses. It is possible to use a copolymer obtained by appropriately combining

For example, in the case of a water-containing soft contact lens material, compounds represented by the general formula [I]: acrylic acid ester, methacrylic acid ester and itaconic acid ester (those represented by the general formula [I] Selected from the group): N-vinyl heterocyclic compounds: crosslinkable polyfunctional monomers = about 95-5: 5-9
The copolymer is preferably composed of a ratio (weight ratio) of 5: 0 to 80: 0.01 to 20. Even more preferably, about 90-10: 5-80: 0-75: 0.0.
The copolymer is preferably composed of 1 to 10 (weight ratio).

In the case of a hard contact lens material, compounds represented by the general formula [I]: Silicon-containing monomers: acrylic acid ester, methacrylic acid ester and itaconic acid ester (represented by the general formula [I] Selected from the group of :), N-vinyl heterocyclic compounds: crosslinkable polyfunctional monomers = about 7
0-5: 5-80: 20-90: 0-20: 0.1-2
It is preferable that the copolymer is composed of 0 (polymerization ratio). Even more preferably, about 50-5: 30.
It is preferably a copolymer composed of 70:20 to 65: 0 to 10: 1 to 15.

Then, the above compounds are blended in a predetermined ratio, and further, for example, dimethyl-2,2'-azobisisobutyrate, 2,2'-azobis (4-methoxy-).
2,4'-dimethylvaleronitrile), 2,2'-azobis (2,4-dimethylvaleronitrile), 2,2'-
A suitable free radical polymerization initiator selected from the group of azobisisobutyl nitrile, benzoylperoxide, diisopropyl peroxydicarbonate and the like is added, and polymerization is carried out by a usual radical polymerization method. As the polymerization method, thermal polymerization, ultraviolet polymerization, radiation polymerization or the like can be adopted.

The polymer block obtained in this manner is cut into the shape of a contact lens or an intraocular lens, or by using a spin casting method, a cast molding method or the like, a contact lens or an intraocular lens. Can be finished. In addition, for the purpose of imparting an ultraviolet absorber, coloring, or cutting light in a partial wavelength region of visible light, an ultraviolet absorber (including a polymerizable type), a dye (polymerizable) Type are also included), ultraviolet absorbing dyes (including polymerizable types), and the like may be used.

In some cases, deterioration due to heat or chemicals (oxidation deterioration, etc.) occurs in the hydrous contact lens material.
For the purpose of preventing the above, antioxidants such as hindered amine derivatives, such as 4-methacryloyloxy-2,
2,6,6-Tetramethylpiperidine, 4-methacryloyloxy-2,2,6,6-tetramethyl-N-piperidine, 4-methacryloylamino-2,2,6,6-
Tetramethylpiperidine, 4-methacryloylamino-
2,2,6,6-tetramethyl-N-methylpiperidine, di (2,2,6,6-tetramethyl-4-piperidyl) itaconate, di (N-methyl-2,2,6,6-)
Tetramethyl-4-piperidyl) itaconate, itaconic acid di (2,2,6,6-tetramethyl-4-piperidyl) amide, itaconic acid di (N-methyl-2,2,6,6)
6-tetramethyl-4-piperidyl) amide or the like may be interposed.

The present invention will be described below with reference to specific examples.

[0032]

【Example】

Example 1 Itaconic acid di-2- (N-acetyl-N-)
75 parts by weight of methyl) aminoethyl (DAMEtIt),
To a mixture of 25 parts by weight of methyl methacrylate (MMA) and 1 part by weight of diallyl itaconate (DAIt), V
0.01 parts by weight of -65 (2,2'-azobis (2,4-dimethylvaleronitrile)) was added and mixed well, and this mixed solution was put into a cylindrical Teflon polymerization tube having a diameter of 16 mm and a height of 10 cm. After pouring and purging the upper space with nitrogen, the temperature was kept at 40 ° C. for 20 hours in an electric oven previously purged with nitrogen, and then at 70 ° C. for 10 hours and 90 ° C. for 10 hours.
Polymerization was carried out by holding at 0 ° C for 10 hours.

The block thus obtained was subjected to ordinary mechanical processing to produce a contact lens. When this contact lens was immersed in physiological saline for 48 hours, it became a hydrous soft contact lens. And this soft contact lens has a water content of 80.2.
%, And was excellent in flexibility, mechanical strength, shape stability and durability.

Example 2 35 parts by weight of itaconic acid α-
2- (N-trifluoroacetyl-N-methyl) aminoethyl β-2- (N-acetyl-N-methyl) aminoethyl (TFAMAMEtIt), 65 parts by weight of 2-hydroxyethyl methacrylate (2-HEMA), 1 Parts by weight DAIt, 0.5 parts by weight ethylene glycol dimethacrylate (EDMA), 0.01 parts by weight V-65
Was carried out in the same manner as in Example 1 to obtain a hydrous soft contact lens.

The obtained soft contact lens is
It had a water content of 47.7% and was excellent in flexibility, mechanical strength, shape stability and durability. Example 3 30 parts by weight of 2- (N-trifluoroacetyl-N-ethyl) aminoisopropyl-2- (N-acetyl-N-methyl) aminoisopropyl fumarate (TFAEAMiPrF), 60 parts by weight of N- Vinyl
2-pyrrolidone (NVP), 10 parts by weight MMA, 1 part by weight allyl methacrylate (AMA), 0.5 parts by weight vinyl methacrylate, 0.01 parts by weight V-65 as in Example 1. Then, a hydrous soft contact lens was obtained.

The obtained soft contact lens is
It had a water content of 57.2% and was excellent in flexibility, mechanical strength, shape stability and durability. Example 4 50 parts by weight of bis (2- (N-acetyl-
N-methyl) aminoisopropyl) malate (DAMi
PrM), 40 parts by weight of 2-HEMA, 10 parts by weight of M
MA, 1 part by weight AMA, 1 part by weight EDMA, 0.0
Using 1 part by weight of V-65, the same procedure as in Example 1 was carried out to obtain a hydrous contact lens.

The obtained soft contact lens is
It had a water content of 67.8% and was excellent in flexibility, mechanical strength, shape stability and durability. [Comparative Example 1] A water-containing soft contact lens was obtained in the same manner as in Example 1, except that NVP was used instead of DAMEtIt.

Comparative Example 2 In Example 2, TFAM
2,2,2-trifluoroethylmethacrylate (3FMA) was used in place of AMEtIt in the same manner to obtain a hydrous soft contact lens. [Comparative Example 3] In Example 3, TFAEAMiPrF
In the same manner as above, 3FMA was used to obtain a hydrous soft contact lens.

COMPARATIVE EXAMPLE 4 In Example 4, DAMi
Similarly, NVP was used instead of PrM to obtain a hydrous soft contact lens. Example 5 45 parts by weight of methacryloxyethoxypropyltris (trimethylsiloxy) silane (MET
S), 20 parts by weight of di-3- (N-trifluoroacetyl-N-methyl) aminopropyl itaconate (DTFA
MPrIt), 22 parts by weight MMA, 8 parts by weight methacrylic acid, 5 parts by weight triethylene glycol dimethacrylate (TGD), 0.03 parts by weight V-601 (dimethyl-2,2'-azobisisobutyrate). ) Was used in the same manner as in Example 1 to obtain a contact lens.

The obtained contact lens was a hard contact lens, and was a hard one having excellent mechanical workability. [Example 6] 45 parts by weight of METS and 25 parts by weight of TF
AMAMEtIt, 25 parts by weight MMA, 5 parts by weight T
Example 1 using GD, 0.03 parts by weight of V-601.
A contact lens was obtained in the same manner as above.

The obtained contact lens was a hard contact lens and was a hard one having excellent mechanical workability. [Example 7] 45 parts by weight of METS and 30 parts by weight of TF
AEAMiPrF, 18 parts by weight MMA, 2 parts by weight E
DMA, 5 parts by weight TGD, 0.03 parts by weight V-60
1 was performed in the same manner as in Example 1 to obtain a contact lens.

The obtained contact lens was a hard contact lens, which was a hard one having excellent mechanical workability. [Comparative Example 5] A hard contact lens was obtained in the same manner as in Example 5, except that hexafluoroisopropyl methacrylate was used instead of DTFAMPrIt.

[Comparative Example 6] In Example 6, TFAM
Do the same with 3FMA instead of AMEtIt,
I got a hard contact lens. [Comparative Example 7] In Example 7, TFAEAMiPrF
In the same manner as above, 3FMA was used to obtain a hard contact lens.

[0044]

[Characteristics] With respect to the soft contact lenses obtained in each of the above examples, the water content, the transparency, the dirt adhering property, and the dirt releasing property were examined. The results are shown in Table 1. Table-1 Water Content (%) Transparency Stain Adhesion Stain Removability Example 1 80.2 Transparency ○ ○ Example 2 47.7 Transparency ◎ ◎ Example 3 57.2 Transparency ○ ◎ Example 4 67 9.8 Transparency ○ ○ Comparative Example 1 72.6 Transparency × × Comparative Example 2 10.9 Slight turbidity ○ △ Comparative Example 3 38.8 White turbidity △ △ Comparative Example 4 49.1 Transparency × × Also, each of the above The hard contact lenses obtained in the examples were examined for their hydrophilic contact angle, transparency, oxygen permeability coefficient, stain adhesion and stain release properties, and the results are shown in Table-2.

Table-2 Hydrophilic Contact Angle Transparency Oxygen Permeability Coefficient Soil Adhesion Stain Removability Example 5 74.6 ° Transparency 37.4 ◎ ◎ Example 6 74.1 ° Transparency 36.2 ◎ ◎ Implementation Example 7 74.3 ° Transparency 37.4 ◎ ◎ Comparative Example 5 83.5 ° Transparency 35.2 ○ △ Comparative Example 6 98.5 ° Transparency 35.7 ○ ○ Comparative Example 7 99.8 ° Transparency 36.9 ○ ○ * The unit of oxygen permeability coefficient is 10 ^-11 ml (STP) cm / cm ² · sec · mmHg [Stain adhesion] The contact lens is immersed in a protein aqueous solution with a concentration of 2 ppm at 37 ° C for 24 hours, After this, the product was taken out and washed with a predetermined amount of purified water, and the washing liquid and the immersion liquid were combined to quantify the residual protein, and the amount of protein attached to the contact lens was determined. ◎ indicates that the amount of protein attached to one contact lens is less than 0.1 μg, ○ indicates that the amount of protein attached to one contact lens is less than 0.5 μg and 0.1 μg or more and less than 1.0 μg. The mark Δ indicates 1.0 μg or more and the mark X indicates.

[Stain Removability] Contact lenses were immersed in a protein aqueous solution having a concentration of 20 ppm at 37 ° C. for 24 hours,
After that, the contact lens was taken out and washed with a predetermined amount of purified water to prepare a contact lens to which dirt was attached. This contact lens is placed in a 0.75% sodium dodecyl sulfate aqueous solution to
The protein was extracted from the contact lens by immersing at 0 ° C. for 24 hours. Then, the contact lens was taken out, the surface was washed with a predetermined amount of 0.75% sodium dodecylsulfate aqueous solution, and the amount of protein in the extract and the extract was determined. One contact lens with a protein mass of 1.5 μg or more is marked with ⊚, 1.0 μg or more and less than 1.5 μg is marked with ◯, and 0.5 μg or more and less than 1.0 μg is marked with Δ. Then, those with less than 0.5 μg are indicated by X marks.

[0047]

[Effect] It has excellent wearability, excellent mechanical properties and durability, is resistant to stains, and is easily removed even if stains occur.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification code Internal reference number FI Technical display location C08F 222/38 MNE C08L 33/08 LJA

Claims (5)

[Claims] 1. A medical material characterized by being polymerized using a compound represented by the following general formula [I]. General formula [I] A-Y-X-Y-B [In the formula [I], X is an unsaturated dicarboxylic acid group, Y is O or NR ₁ (provided that Y is the same or different. good). R ₁ is a hydrogen atom, or a chain-like (straight or branched chain) alkyl group having 1 to 8 carbon atoms, a chain-like (straight chain or branched chain) hydroxyalkyl group having 1 to 8 carbon atoms, And a group selected from the group of aryl groups. A and B are the same or different groups, and at least one group of A and B is represented by the general formula [II]. When only one of A and B is represented by the general formula [II], the other of A and B is a hydrogen atom or a chain (having a straight chain or a branched chain) having 1 to 20 carbon atoms. Group, cyclic alkyl group having 4 to 12 carbon atoms, chain-like (which may be linear or branched) hydroxyalkyl group having 1 to 8 carbon atoms, chain-like (having straight chain or branched chain) having 1 to 15 carbon atoms Good) halogenated alkyl group, cyclic halogenated alkyl group having 4 to 12 carbon atoms, aryl group, halogenated aryl group,-(CH ₂ CH ₂ O) pH (p
Is an integer of 2 to 10), —CH ₂ CH ₂ (OH) CH ₂ — (O) rR ₂ (R ₂ is a linear (branched or branched) alkyl group having 1 to 15 carbon atoms) , R is a group selected from the group of 0 or 1). ] Formula - in (II) _{(CR 3 R 4) n- (} CR 5 R 6) mN (R 7) -C (R 8) 0 [Formula _{(II), R 3, R 4, R} 5, R ₆ , R ₇ , R ₈
(R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , and R ₈ may be the same or different) is a hydrogen atom, or 1 to
20 linear (branched or branched) alkyl groups,
A cyclic alkyl group having 4 to 12 carbon atoms, a chain (straight or branched) halogenated alkyl group having 1 to 15 carbon atoms, a cyclic halogenated alkyl group having 4 to 12 carbon atoms, an aryl group, A group selected from the group of aryl halide groups. R ₇ may be a chain-like (straight chain or branched chain) hydroxyalkyl group having 1 to 8 carbon atoms. n,
m is an integer from 0 to 6] 2. The medical material according to claim 1, further comprising a copolymerizable compound used for copolymerization. 3. The medical material according to claim 1, wherein X in the general formula [I] is an itaconic acid group. 4. The medical material according to claim 1, wherein X in the general formula [I] is a fumaric acid group. 5. The medical material according to claim 1, wherein X in the general formula [I] is a maleic acid group.