JPH09189887A - Ocular lens material - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an ocular lens material which has excellent oxygen permeability and transparincy and simultaneously has hydrophilicity, such as adequate wettability with water, by polymerizing a polynm. component contg. a prescribed silicon-contg. compd. SOLUTION: This ocular lens material consists of the polymer obtd. by polymerizing the polymn. component contg. the silicon-contg. compd. expressed by formula I. In the formula I, R<1> denotes 1 to 6C alkylene group; A denotes formula II. In the formula II, R<2> denotes a hydrogen atom or methyl group; R<3> denotes 1 to 6C tervalent hydrocarbon group or 1 to 6C bivalent hydrocarbon group when R<4> is a hydrogen atom; R<4> denotes a hydrogen atom, hydroxyl group, 1 to 6C alkyl group, etc. This silicon-contg. compd. has copolymerizability and is good in compatibility with both of a hydrophobic component and hydrophilic component. Then, the compd. has the property to impart a release property, shape stability, durability, etc., to the ocular lens material in addition to the property to impart the excellent oxygen permeability and transparency as well as the adequate hydrophilicity thereto.

Description

Detailed Description of the Invention

[0001]

The present invention relates to an ophthalmic lens material. More specifically, it has excellent oxygen permeability and transparency, and at the same time has an appropriate hydrophilicity, and at the same time has excellent releasability, shape stability, durability, slipperiness, low abrasion resistance, antithrombogenicity, etc. Lens, intraocular lens,
The present invention relates to an ophthalmic lens material that can be suitably used for artificial corneas and the like.

[0002]

2. Description of the Related Art Conventionally, it has been known that an acrylic polymer having a polysiloxane group introduced therein has excellent light resistance, releasability and water repellency. Therefore,
Various molded products have been proposed which utilize the characteristics of the acrylic polymer having such a polysiloxane group introduced therein, and among them, for example, development of optical transparent materials such as eye lens materials is in progress.

As the ophthalmic lens material, for example, a material containing polymethylmethacrylate as a main component has been put into practical use. However, although the material containing polymethylmethacrylate as a main component has a great advantage that it has excellent optical properties and mechanical properties such as transparency,
It has a problem of poor oxygen permeability.

For example, a contact lens obtained from such an ophthalmic lens material having poor oxygen permeability lowers the amount of oxygen supplied to the eyeball, and therefore, when such a contact lens is worn on the eye for a long time. Is hyperemia,
There was a great risk of causing edema and other corneal disorders.

Therefore, in order to improve the oxygen permeability of the methacrylic acid ester-based polymer such as the polymethylmethacrylate, focusing on the use of a monomer in which a large amount of silicon atom is introduced into the molecule of the methacrylic acid ester-based monomer, A contact lens composed of a copolymer of an oligosiloxanylalkyl (meth) acrylate monomer having an oligosiloxane bond introduced into the molecule of a methacrylic acid ester monomer and a methacrylic acid ester monomer has been proposed.

However, the contact lens is
Compared with contact lenses made from conventional methacrylic acid ester-based polymers such as polymethylmethacrylate, its oxygen permeability is improved, but it satisfies the oxygen permeability required for ophthalmic lenses such as contact lenses. However, the development of materials having excellent oxygen permeability has been eagerly awaited.

[0007] Generally, when an attempt is made to improve the oxygen permeability of a material, the hydrophilicity such as water wettability is lowered too much, and the hydrophilicity particularly required for an ophthalmic lens material is There is a problem that the material does not have even.

In particular, a polymer obtained by using the oligosiloxanylalkyl (meth) acrylate-based monomer as an essential component is extremely wettable by water, so that an eye lens is obtained from such a polymer. In the meantime, there is a problem that a complicated secondary surface modification such as a discharge treatment such as a plasma treatment must be performed.

[0009]

SUMMARY OF THE INVENTION The present invention has been made in view of the above-mentioned prior art, and in particular, it has excellent oxygen permeability and transparency, and at the same time has suitable hydrophilicity such as water wettability, It is an object of the present invention to provide an ophthalmic lens material excellent in moldability, shape stability, durability and the like at the same time.

[0010]

According to the present invention, there is provided a compound represented by the general formula (I):

[0011]

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(Wherein R ¹ is an alkylene group having 1 to 6 carbon atoms, A is a general formula (II):

[0013]

[Chemical 6]

(In the formula, R ² is a hydrogen atom or a methyl group,
R ³ is a divalent hydrocarbon group having 1 to 6 carbon atoms when hydrocarbon group or R ⁴ trivalent having 1 to 6 carbon atoms is a hydrogen atom, R ⁴ is a hydrogen atom, a hydroxyl group, having 1 to 6 carbon atoms Alkyl group or general formula (III):

[0015]

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(Wherein R ⁵ represents an alkylene group having 1 to 6 carbon atoms, m represents an integer of 1 to 15) or a group represented by the general formula (IV):

[0017]

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(In the formula, R ⁶ is a hydrogen atom or a methyl group,
R ⁷ represents a direct bond or a group represented by an alkylene group having 1 to 6 carbon atoms), and n represents an integer of 1 to 15), and was obtained by polymerizing a polymerization component containing a silicon-containing compound represented by It relates to an ophthalmic lens material made of a polymer.

[0019]

BEST MODE FOR CARRYING OUT THE INVENTION As described above, the ophthalmic lens material of the present invention has the general formula (I):

[0020]

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(Wherein R ¹ is an alkylene group having 1 to 6 carbon atoms, and A is a general formula (II):

[0022]

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(Wherein R ² is a hydrogen atom or a methyl group,
R ³ is a divalent hydrocarbon group having 1 to 6 carbon atoms when hydrocarbon group or R ⁴ trivalent having 1 to 6 carbon atoms is a hydrogen atom, R ⁴ is a hydrogen atom, a hydroxyl group, having 1 to 6 carbon atoms Alkyl group or general formula (III):

[0024]

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(In the formula, R ⁵ represents an alkylene group having 1 to 6 carbon atoms, m represents an integer of 1 to 15) or a group represented by the general formula (IV):

[0026]

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(In the formula, R ⁶ is a hydrogen atom or a methyl group,
R ⁷ represents a direct bond or a group represented by an alkylene group having 1 to 6 carbon atoms), and n represents an integer of 1 to 15), and was obtained by polymerizing a polymerization component containing a silicon-containing compound represented by It is obtained from a polymer.

Since the silicon-containing compound represented by the general formula (I) has two polar groups in the molecule,
It has not only homopolymerizability but also copolymerizability, and also has good compatibility with both hydrophobic and hydrophilic components, and has excellent oxygen permeability and transparency in the obtained ocular lens material and It is a compound having properties such as releasing property, shape stability, and durability in addition to imparting appropriate hydrophilicity.

In the above general formula (I), R ¹ is an alkylene group having 1 to 6 carbon atoms, but the compatibility of the silicon-containing compound with other polymerization components and the processability of the obtained polymer are good. From the viewpoint that it is present, an alkylene group having 2 to 4 carbon atoms is preferable. When the number of carbon atoms of the alkylene group representing R ¹ is 7 or more, the viscosity of the silicon-containing compound becomes too high and the handling becomes difficult, and the obtained polymer becomes too soft, resulting in poor processability. It is not preferable because it decreases.

A is a group represented by the general formula (II) or a group represented by the general formula (IV), and the general formula (I
In I), R ³ is a trivalent hydrocarbon group having 1 to 6 carbon atoms or a divalent hydrocarbon group having 1 to 6 carbon atoms when R ⁴ is a hydrogen atom. From the viewpoint of compatibility with the components and good processability of the obtained polymer, it is a trivalent hydrocarbon group having 2 to 4 carbon atoms or a divalent hydrocarbon group having 2 to 4 carbon atoms. Is preferred. When the carbon number of the trivalent hydrocarbon group or the divalent hydrocarbon group representing R ³ is 7 or more, the viscosity of the silicon-containing compound becomes too high, which makes the handling difficult.
Further, the obtained polymer becomes too soft and the processability is deteriorated, which is not preferable.

Further, in the general formula (II), R ⁴ is usually a hydrogen atom, but considering that the effect of imparting water wettability is great, a hydroxyl group or the general formula (III) is used.
It may be substituted with a group represented by (hereinafter referred to as SiU group). In the SiU group, R ⁵ is an alkylene group having 1 to 6 carbon atoms, but from the viewpoint that the compatibility between the silicon-containing compound and other polymerization components and the processability of the obtained polymer are good. It is preferably an alkylene group having 2 to 4 carbon atoms. When the number of carbon atoms of the alkylene group representing R ⁵ is 7 or more, the viscosity of the silicon-containing compound becomes too high and the handling becomes difficult, and the resulting polymer becomes too soft and the processability deteriorates. So
Not preferred. Further, in the SiU group, m is 1 to 1
It is an integer of 5, but is preferably an integer of 2 to 10 and more preferably 3 to 6 from the viewpoint of good compatibility between the silicon-containing compound and other polymerization components and good processability of the obtained polymer. Is preferably an integer. Such m is 1
When it is an integer of 6 or more, the viscosity of the silicon-containing compound is excessively increased to make it difficult to handle, and the resulting polymer is too soft to reduce the processability, which is not preferable.

Further, in the above general formula (I), n is an integer of 1 to 15, but it is said that the compatibility between the silicon-containing compound and other polymerization components and the processability of the obtained polymer are good. From the viewpoint, it is desirable that the integer is preferably 2 to 10, and more preferably 3 to 6. When n is an integer of 16 or more, the viscosity of the silicon-containing compound increases too much to make it difficult to handle, and the resulting polymer becomes too soft to reduce the processability, which is not preferable.

Specific examples of the silicon-containing compound include N-pentamethyldisiloxanylmethyl (meth) acryloxyethylcarbamate, N-trimethylsiloxydimethylsilylpropyl (meth) acryloxyethylcarbamate, and N-methylbis ( Trimethylsiloxy) silylpropyl (meth) acryloxyethylcarbamate, N-tris (trimethylsiloxy) silylpropyl (meth) acryloxyethylcarbamate,
N-mono [methylbis (trimethylsiloxy) siloxy] bis (trimethylsiloxy) silylpropyl (meth) acryloxyethylcarbamate, N-tris [methylbis (trimethylsiloxy) siloxy] silylpropyl (meth) acryloxyethylcarbamate, N-trimethylsilyl Methyl (meth) acryloxyethyl carbamate, N-trimethylsilylpropyl (meth) acryloxyethyl carbamate, N-methylbis (trimethylsiloxy) silylethyl tetramethyldisiloxanylmethyl (meth) acryloxyethyl carbamate, N
-Trimethylsiloxydimethylsilylpropyl (meth)
Acryloxyethyl carbamate, N-pentamethyldisiloxanylmethyl vinylphenyl carbamate, N-
Trimethylsiloxydimethylsilylpropyl vinylphenyl carbamate, N-methylbis (trimethylsiloxy) silylpropyl vinylphenyl carbamate, N-
Tris (trimethylsiloxy) silylpropylvinylphenylcarbamate, N-mono [methylbis (trimethylsiloxy) siloxy] bis (trimethylsiloxy) silylpropylvinylphenylcarbamate, N-tris [methylbis (trimethylsiloxy) siloxy] silylpropylvinylphenylcarbamate, N-trimethylsilylmethylvinylphenylcarbamate, N-trimethylsilylpropylvinylphenylcarbamate, N-
Examples thereof include methylbis (trimethylsiloxy) silylethyltetramethyldisiloxanylmethylvinylphenylcarbamate and N-trimethylsiloxydimethylsilylpropylvinylphenylcarbamate. These may be used alone or in combination of two or more.

In the present specification, "... (meth) acryl ~" means "... acryl ~ and / or ...
・ ・ Methacrylic

The reason why the silicon-containing compound has excellent polymerizability is that it contains a polymerizable unsaturated double bond of an acryloyl group, a methacryloyl group or a vinylphenyl group in its structure.

Further, since the silicon-containing compound contains silicon in its structure, the polymer obtained by polymerizing the compound exhibits excellent oxygen permeability.

Further, the silicon-containing compound has, in addition to a urethane bond, a hydroxyl group as R ⁴ in the general formula (II) and a urethane bond in the SiU group as R ⁴ in its structure. Therefore, the polymer obtained by polymerizing such a compound also exhibits good hydrophilicity.

The content of the above-mentioned silicon-containing compound is sufficient for sufficiently exhibiting the effect of using the compound, particularly the effect of imparting excellent oxygen permeability and moderate hydrophilicity to the ophthalmic lens material. It is desirable that the amount is adjusted to 5% by weight or more, preferably 10% by weight or more, and more preferably 20% by weight or more of the total amount of the polymerization components.
Further, in the present invention, the total amount of the polymerization component may be the silicon-containing compound, but in consideration of the mechanical strength and processability of the obtained polymer, the content of the silicon-containing compound is the total amount of the polymerization component. It is desirable to adjust the content to 95% by weight or less, preferably 90% by weight or less.

As described above, the ophthalmic lens material of the present invention may be composed of a polymer obtained by polymerizing a polymerization component containing only the silicon-containing compound represented by the general formula (I). Although it is good, it is composed of a polymer obtained by polymerizing a polymerization component that also contains a polymerizable monomer having an unsaturated double bond copolymerizable with the silicon-containing compound (hereinafter referred to as a polymerizable monomer). Good. The type of the polymerizable monomer is not particularly limited as long as the object of the present invention is not impaired.

The polymerizable monomer is appropriately selected according to the properties of the intended ophthalmic lens material, and the total amount of the polymerizable components is 1
The content can be appropriately adjusted and used so as to be 00% by weight. For example, when obtaining a non-hydrous ophthalmic lens material, a hydrophobic monomer or macromonomer is mainly selected, and when obtaining a hydrous ophthalmic lens material, a hydrophilic monomer or macromonomer is used. The monomer or macromonomer may be mainly selected. When obtaining an ophthalmic lens material with excellent mechanical strength, select a reinforcing monomer or macromonomer to obtain an ophthalmic lens material with excellent water resistance and solvent resistance. In that case, a crosslinkable monomer for forming a crosslinked structure may be selected.

Specifically, for example, when it is desired to further impart oxygen permeability to the obtained ocular lens material and at the same time to reinforce the mechanical strength of the ophthalmic lens material,
For example, a polysiloxane macromonomer having a polymerizable group bonded to the siloxane main chain through one or two urethane bonds, a polysiloxane macromonomer having a polymerizable group directly bonded to the siloxane main chain, a polymerizable group A polysiloxane macromonomer such as a polysiloxane macromonomer in which is bonded to the siloxane main chain via an alkylene group is used.

Examples of the polysiloxane macromonomer have the formula:

[0043]

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Polyurethane bond-containing polysiloxane macromonomer represented by (hereinafter referred to as macromonomer a)
Formula such as ^{(V): A 1 - (} U 2) m2 -S 3 - (T 4) m4 - (U 5) m5 -A 6 (V) ( wherein, A ¹ is the general formula: Y ¹¹ - R ¹² - (wherein, Y ¹¹ is acryloyloxy group, methacryloyloxy group, a vinyl group or an allyl group, R ¹² is 1 to carbon atoms
A ⁶ represents a linear or branched alkylene group; A ⁶ represents a general formula: —R ⁶² —Y ⁶¹ (where R ⁶² represents a linear or branched C 1-6 alkyl group) A chain alkylene group, Y ⁶¹ represents an acryloyloxy group, a methacryloyloxy group, a vinyl group or an allyl group), and U ² represents a general formula: -X ²¹ -E ²² -X ²³ -R ^24- ( In the formula, X ²¹ is a covalent bond, an oxygen atom or a group having 1 to 6 carbon atoms.
Alkylene glycol group, E ²² is -NHCO- group or a saturated aliphatic, ends derived from diisocyanates selected from cycloaliphatic and aromatic systems -CONH- group and -NH
A divalent group that is a CO- group, X ²³ is an oxygen atom, and has 1 carbon atom
To 6 alkylene glycol groups or a general formula:

[0045]

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(Wherein R ²³⁵ is a trivalent hydrocarbon group having 1 to 6 carbon atoms, R ²³² is a linear or branched alkylene group having 1 to 6 carbon atoms, and E ²³⁴ is a -CONH- group. Alternatively, a diisocyanate-derived terminal selected from a saturated aliphatic group, an alicyclic group and an aromatic group has a -CONH- group and a -NHCO- group.
A divalent group which is a group, X ²³³ is a covalent bond, an oxygen atom or an alkylene glycol group having 1 to 6 carbon atoms, and Y ²³¹ is an acryloyloxy group, a methacryloyloxy group, a vinyl group or an allyl group (provided that X is ²³³ is a covalent bond when adjacent E ²³⁴ is a -CONH- group, and is an oxygen atom or a carbon number of 1 to 6 when adjacent E ²³⁴ is a divalent group derived from diisocyanate. It is an alkylene glycol group, and E ²³⁴ forms a urethane bond between the adjacent oxygen atom and X ²³³ )).
And R ²⁴ represents a linear or branched alkylene group having 1 to 6 carbon atoms (provided that X ²¹ is a covalent bond when adjacent E ²² is a —NHCO— group. And when adjacent E ²² is a diisocyanate-derived divalent group, it is an oxygen atom or an alkylene glycol group having 1 to 6 carbon atoms, and E ²² is adjacent X ²¹ and X ^23.
Groups represented by by forming a urethane bond)) during the, U ⁵ has the general ^{formula: -R 54 -X 53 -E 52 -X} 51 - ( wherein, R ⁵⁴ is 1 to 6 carbon atoms straight A chain or branched alkylene group, X ⁵³ is an oxygen atom, an alkylene glycol group having 1 to 6 carbon atoms or a general formula:

[0047]

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(In the formula, R ⁵³⁵ is a trivalent hydrocarbon group having 1 to 6 carbon atoms, R ⁵³² is a linear or branched alkylene group having 1 to 6 carbon atoms, and E ⁵³⁴ is a -CONH- group. Alternatively, a diisocyanate-derived terminal selected from a saturated aliphatic group, an alicyclic group and an aromatic group has a -CONH- group and a -NHCO- group.
A divalent group as a group, X ⁵³³ is a covalent bond, an oxygen atom or an alkylene glycol group having 1 to 6 carbon atoms, and Y ⁵³¹ is an acryloyloxy group, a methacryloyloxy group, a vinyl group or an allyl group (provided that X is ⁵³³ is a covalent bond when the adjacent E ⁵³⁴ is a —CONH— group, and an oxygen atom or a carbon number of 1 to 6 when the adjacent E ⁵³⁴ is a diisocyanate-derived divalent group. It is an alkylene glycol group, and E ⁵³⁴ forms a urethane bond between the adjacent oxygen atom and X ⁵³³ ))
The group represented by the formula, E ⁵² is a -CONH- group or a diisocyanate-derived terminal selected from a saturated aliphatic group, an alicyclic group and an aromatic group is a -CONH- group and a -NHCO- group 2 A valent group, X ^51, represents a covalent bond, an oxygen atom or an alkylene glycol group having 1 to 6 carbon atoms (provided that X is
⁵¹ is a covalent bond when the adjacent E ⁵² is a —CONH— group, and an oxygen atom or a C 1 to C 6 group when the adjacent E ⁵² is a diisocyanate-derived divalent group. Is an alkylene glycol group, and E ⁵² is adjacent to X ⁵¹
And forming a urethane bond between the X ⁵³⁾⁾
S ³ is a group represented by the general formula:

[0049]

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(Wherein R ³¹ , R ³² , R ³³ , R ³⁵ and R
³⁶ are independently straight or branched alkyl group or a phenyl group part or all of 1 to 6 carbon atoms which may be substituted with a fluorine atom of the hydrogen atoms, one R ³⁴ is a hydrogen atom A part or all of which may be substituted with a fluorine atom, a linear or branched alkyl group having 1 to 6 carbon atoms, a phenyl group or a general formula:

[0051]

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(In the formula, R ³⁴⁶ and R ³⁴² are each independently a linear or branched alkylene group having 1 to 6 carbon atoms, X ³⁴⁵ and X ³⁴³ are covalent bonds, oxygen atoms or 1 to carbon atoms. 6 alkylene glycol group, E ³⁴⁴ is -CON
H-group or a terminal derived from a diisocyanate selected from saturated aliphatic group, alicyclic group and aromatic group is -CONH-
A divalent group which is a group and a —NHCO— group, Y ³⁴¹ represents an acryloyloxy group, a methacryloyloxy group, a vinyl group or an allyl group (provided that X ³⁴⁵ and X ³⁴³ are —CONH— when adjacent E ³⁴⁴ are —CONH—). When it is a group, each is a covalent bond, and when adjacent E ³⁴⁴ is a diisocyanate-derived divalent group, each is an oxygen atom or an alkylene glycol group having 1 to 6 carbon atoms, and E
³⁴⁴ represents a group represented by the following formula (which forms a urethane bond between adjacent X ³⁴⁵ and X ³⁴³ ), provided that all of R ³¹ , R ³² , R ³³ , R ³⁴ , R ³⁵ and R ³⁶ are At the same time, m31 is a linear or branched alkyl group having 1 to 6 carbon atoms in which part or all of the hydrogen atoms are substituted with a fluorine atom, or a phenyl group). An integer of 1 to 100, m32 is 0 to (10
0- (m31)) (provided that (m31) +
(M32) is a group represented by indicating)) an integer from 1 to 100, T ⁴ has the general formula: -U ⁴¹ -S ⁴² - (wherein, U ⁴¹ the general formula: -R ⁴¹¹ -X ⁴¹² -E ⁴¹³ —X ⁴¹⁴ —R ⁴¹⁵ — (wherein, R ⁴¹¹ and R ⁴¹⁵ each independently have 1 carbon atom)
~ 6 linear or branched alkylene group, X ⁴¹² and X ⁴¹⁴ are each independently an oxygen atom, or an alkylene glycol group having 1 to 6 carbon atoms, and E ⁴¹³ is a saturated aliphatic group or alicyclic group. And a diisocyanate-derived terminal selected from an aromatic group represents a divalent group having a -CONH- group and a -NHCO- group (provided that E ⁴¹³ is adjacent to X ^412).
And a urethane bond is formed between X ⁴¹⁴ )) and S ⁴² has the general formula:

[0053]

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(In the formula, R ⁴²¹ , R ⁴²² , R ⁴²³ , R ⁴²⁵ and R ⁴²⁶ are each independently a straight chain having 1 to 6 carbon atoms in which a part or all of hydrogen atoms may be substituted with a fluorine atom. Chain or branched alkyl group or phenyl group,
R ⁴²⁴ represents a linear or branched alkyl group having 1 to 6 carbon atoms which may be partially or entirely substituted with a fluorine atom, a phenyl group or a general formula:

[0055]

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(In the formula, R ⁴²⁴⁶ and R ⁴²⁴² are each independently a linear or branched alkylene group having 1 to 6 carbon atoms, X ⁴²⁴⁵ and X ⁴²⁴³ are a covalent bond, an oxygen atom or 1 to 4 carbon atoms. 6 alkylene glycol group, E ⁴²⁴⁴ is -C
The terminal derived from an ONH-group or a diisocyanate selected from a saturated aliphatic group, an alicyclic group and an aromatic group is -CON.
A divalent group which is an H-group and an -NHCO- group, Y ⁴²⁴¹ represents an acryloyloxy group, a methacryloyloxy group, a vinyl group or an allyl group (provided that X ⁴²⁴⁵ and X ^{4243 are present.
Are} each a covalent bond when adjacent E ⁴²⁴⁴ is a -CONH- group, and each is an oxygen atom or a carbon number of 1 to 6 when adjacent E ⁴²⁴⁴ is a diisocyanate-derived divalent group. An alkylene glycol group of
⁴²⁴⁴ represents a group represented by the following ^formula (which forms a urethane bond between adjacent X ⁴²⁴⁵ and X ⁴²⁴³ ) (provided that R ⁴²¹ , R ⁴²² , R ⁴²³ , R ⁴²⁴ , R ⁴²⁵ and R ⁴²⁶ are all At the same time, when a hydrogen atom is partly or wholly substituted with a fluorine atom, a linear or branched alkyl group having 1 to 6 carbon atoms or a phenyl group is excluded, and m421 is excluded. An integer of 1 to 100, and m422 represents an integer of 0 to (100- (m421)) (however,
(M421) + (m422) represents an integer of 1 to 100)) or a general formula:

[0057]

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(Where T ⁴³ is a general formula:

[0059]

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(In the formula, R ⁴³¹ , R ⁴³⁵ and R ⁴³⁷ are each independently a linear or branched alkylene group having 1 to 6 carbon atoms, and X ⁴³² , X ⁴³⁴ and X ⁴³⁶ are each independently. An oxygen atom or an alkylene glycol group having 1 to 6 carbon atoms, T ⁴³³ has the formula:

[0061]

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A group represented by the formula (provided that a urethane bond is formed between adjacent X ⁴²³ , X ⁴³⁴ and X ⁴³⁶ ) and S ⁴⁴ has the general formula:

[0063]

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(In the formula, R ⁴⁴¹ , R ⁴⁴² , R ⁴⁴³ , R ⁴⁴⁵ and R ⁴⁴⁶ are each independently a straight chain having 1 to 6 carbon atoms in which some or all of hydrogen atoms may be substituted with fluorine atoms. Chain or branched alkyl group or phenyl group,
R ⁴⁴⁴ is a linear or branched alkyl group having 1 to 6 carbon atoms which may be partially or entirely substituted with a fluorine atom, a phenyl group or a general formula:

[0065]

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(In the formula, R ⁴⁴⁴⁶ and R ⁴⁴⁴² are each independently a straight-chain or branched-chain alkylene group having 1 to 6 carbon atoms, X ⁴⁴⁴⁵ and X ⁴⁴⁴³ are covalent bonds, oxygen atoms or 1 to 6 carbon atoms. 6 alkylene glycol group, E ⁴⁴⁴⁴ is -C
The terminal derived from an ONH-group or a diisocyanate selected from a saturated aliphatic group, an alicyclic group and an aromatic group is -CON.
A divalent group of H- and -NHCO-, Y ⁴⁴⁴¹ represents an acryloyloxy group, a methacryloyloxy group, a vinyl group or an allyl group (provided that X ⁴⁴⁴⁵ and X ⁴⁴⁴³
Are each a covalent bond when adjacent E ⁴⁴⁴⁴ is a -CONH- group, and are each an oxygen atom or a carbon number of 1 to 6 when adjacent E ⁴⁴⁴⁴ is a diisocyanate-derived divalent group. An alkylene glycol group of
⁴⁴⁴⁴ represents a group represented by the following formula (forming a urethane bond between adjacent X ⁴⁴⁴⁵ and X ⁴⁴⁴³ ), provided that all of R ⁴⁴¹ , R ⁴⁴² , R ⁴⁴³ , R ⁴⁴⁴ , R ⁴⁴⁵ and R ⁴⁴⁶ are represented by At the same time, except for a linear or branched alkyl group having 1 to 6 carbon atoms in which part or all of the hydrogen atoms are substituted with a fluorine atom, or a phenyl group), m441 is An integer of 1 to 100, m442 represents an integer of 0 to (100- (m441)) (however,
(M441) + (m442) is an integer of 1 to 100), and S ⁴⁵ is a general formula:

[0067]

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(In the formula, R ⁴⁵¹ , R ⁴⁵² , R ⁴⁵³ , R ⁴⁵⁵ and R ⁴⁵⁶ are each independently a straight chain having 1 to 6 carbon atoms in which a part or all of hydrogen atoms may be substituted with a fluorine atom. Chain or branched alkyl group or phenyl group,
R ⁴⁵⁴ is a linear or branched alkyl group having 1 to 6 carbon atoms, a phenyl group or a general formula, wherein a part or all of hydrogen atoms may be substituted by a fluorine atom.

[0069]

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(In the formula, R ⁴⁵⁴⁶ and R ⁴⁵⁴² are each independently a linear or branched alkylene group having 1 to 6 carbon atoms, X ⁴⁵⁴⁵ and X ⁴⁵⁴³ are covalent bonds, oxygen atoms or 1 to 6 carbon atoms. 6 alkylene glycol group, E ⁴⁵⁴⁴ is -C
The terminal derived from an ONH-group or a diisocyanate selected from a saturated aliphatic group, an alicyclic group and an aromatic group is -CON.
A divalent group represented by an H-group and an -NHCO- group, Y ^4541, represents an acryloyloxy group, a methacryloyloxy group, a vinyl group or an allyl group (provided that X ⁴⁵⁴⁵ and X ⁴⁵⁴³
Are each a covalent bond when adjacent E ⁴⁵⁴⁴ is a -CONH- group, and each is an oxygen atom or a carbon number of 1 to 6 when adjacent E ⁴⁵⁴⁴ is a diisocyanate-derived divalent group. An alkylene glycol group of
⁴⁵⁴⁴ represents a group represented by the following formula (forming a urethane bond between adjacent X ⁴⁵⁴⁵ and X ⁴⁵⁴³ ), provided that all of R ⁴⁵¹ , R ⁴⁵² , R ⁴⁵³ , R ⁴⁵⁴ , R ⁴⁵⁵ and R ⁴⁵⁶ are At the same time, excluding the case where the hydrogen atom is a linear or branched alkyl group having 1 to 6 carbon atoms in which part or all of the hydrogen atoms are substituted with a fluorine atom, or the case where it is a phenyl group), m451 is An integer of 1 to 100, and m452 represents an integer of 0 to (100- (m451)) (however,
(M451) + (m452) represents an integer of 1 to 100)), and U ⁴⁶ is a general formula: —R ⁴⁶¹ —X ⁴⁶² —E ⁴⁶³ —X ⁴⁶⁴ — (wherein R ⁴⁶¹ is the number of carbon atoms) A linear or branched alkylene group having 1 to 6 carbon atoms, X ⁴⁶² is an oxygen atom, an alkylene glycol group having 1 to 6 carbon atoms or a general formula:

[0071]

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(In the formula, R ⁴⁶²⁵ is a trivalent hydrocarbon group having 1 to 6 carbon atoms, R ⁴⁶²² is a linear or branched alkylene group having 1 to 6 carbon atoms, and E ⁴⁶²⁴ is a -CONH- group. Alternatively, a diisocyanate-derived terminal selected from a saturated aliphatic group, an alicyclic group and an aromatic group has a -CONH- group and a -NHCO- group.
A divalent group which is a group, X ⁴⁶²³ represents a covalent bond, an oxygen atom or an alkylene glycol group having 1 to 6 carbon atoms, and Y ⁴⁶²¹ represents an acryloyloxy group, a methacryloyloxy group, a vinyl group or an allyl group (provided that X is ⁴⁶²³ is a covalent bond when the adjacent E ⁴⁶²⁴ is a -CONH- group, and an oxygen atom or a carbon number of 1 to 6 when the adjacent E ⁴⁶²⁴ is a diisocyanate-derived divalent group. It is an alkylene glycol group, and E ⁴⁶²⁴ forms a urethane bond between the adjacent oxygen atom and X ⁴⁶²³ )).
The group represented by E ⁴⁶³ is a -CONH- group or a diisocyanate-derived terminal selected from a saturated aliphatic group, an alicyclic group and an aromatic group is a -CONH- group and a -NHCO- group 2 A valent group, X ⁴⁶⁴ represents a covalent bond, an oxygen atom or an alkylene glycol group having 1 to 6 carbon atoms (provided that X ⁴⁶⁴ is a covalent bond when adjacent E ⁴⁶³ is a -CONH- group, When the adjacent E ⁴⁶³ is a diisocyanate-derived divalent group, it is an oxygen atom or an alkylene glycol group having 1 to 6 carbon atoms, and E ⁴⁶³ is
Group represented by to form a urethane bond are)) in between the adjacent X ⁴⁶² and X ^464, A ⁴⁷ has the general formula: -R ⁴⁷² -Y ⁴⁷¹ (wherein, R ⁴⁷² is 1 to 6 carbon atoms straight A chain or branched alkylene group, Y ⁴⁷¹ represents an acryloyloxy group, a methacryloyloxy group, a vinyl group or an allyl group)
M2 represents 0 or 1, m4 represents 0, 1, 2 or 3, m5 represents 0 or 1, provided that m2, m5 and m46 represent All the same))).

The polysiloxane macromonomers can be used alone or in admixture of two or more, and the content thereof may be appropriately adjusted according to the properties of the intended eye lens material. For example, when an ophthalmic lens material having a low water content and a high oxygen permeability is to be obtained, the polysiloxane macromonomer must be added in order to sufficiently exhibit the oxygen permeability improving effect and the mechanical strength reinforcing effect. The content of
It is desirable to adjust the content to be 2% by weight or more, preferably 5% by weight or more, and more preferably 10% by weight or more based on the total amount of the polymerization components, and in order to eliminate the possibility of decreasing the compatibility with other polymerization components. Is preferably adjusted to 30% by weight or less, preferably 20% by weight or less, and more preferably 15% by weight or less of the total amount of the polymerization components.

For example, in order to further improve the oxygen permeability of the obtained ophthalmic lens material, for example, a silicon-containing alkyl (meth) acrylate, a silicon-containing styrene derivative, an alkylvinylsilane, etc.
A silicon-containing monomer other than the silicon-containing compound represented by the general formula (I) is used.

Examples of the silicon-containing alkyl (meth) acrylate include pentamethyldisiloxanylmethyl (meth) acrylate, trimethylsiloxydimethylsilylpropyl (meth) acrylate, methylbis (trimethylsiloxy) silylpropyl (meth) acrylate, tris. (Trimethylsiloxy) silylpropyl (meth) acrylate, mono [methylbis (trimethylsiloxy) siloxy] bis (trimethylsiloxy) silylpropyl (meth) acrylate, tris [methylbis (trimethylsiloxy) siloxy] silylpropyl (meth) acrylate, methyl [ Bis (trimethylsiloxy)] silylpropylglyceryl (meth) acrylate, tris (trimethylsiloxy) silylpropylglyceryl (meth) acry Over DOO, mono [methylbis (trimethylsiloxy) siloxy] bis (trimethylsiloxy) silyl propyl glyceryl (meth) acrylate,
Trimethylsilylethyltetramethyldisiloxanylpropyl glyceryl (meth) acrylate, trimethylsilylmethyl (meth) acrylate, trimethylsilylpropyl (meth) acrylate, trimethylsilylpropyl glyceryl (meth) acrylate, pentamethyldisiloxanylpropyl glyceryl (meth) acrylate,
Methyl bis (trimethylsiloxy) silylethyltetramethyldisiloxanylmethyl (meth) acrylate, tetramethyltriisopropylcyclotetrasiloxanylpropyl (meth) acrylate, tetramethyltriisopropylcyclotetrasiloxybis (trimethylsiloxy) silylpropyl (meth) A) acrylates and organopolysiloxane-containing alkyl (meth) acrylates such as acrylate and trimethylsiloxydimethylsilylpropyl (meth) acrylate.

Examples of the silicon-containing styrene derivative include those represented by the general formula (VI):

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Organopolysiloxane-containing styrene derivatives represented by the formula (s is an integer of 1 to 15, t is 0 or 1, and r is an integer of 1 to 15). In addition, in the organopolysiloxane-containing styrene derivative represented by the general formula (VI), when s or r is an integer of 16 or more, its synthesis and purification become difficult, and further, an ophthalmic lens to be obtained. The hardness of the material tends to decrease. Further, when t is an integer of 2 or more, the synthesis of the organopolysiloxane-containing styrene derivative tends to be difficult.

Typical examples of the styrene derivative represented by the general formula (VI) include, for example, tris (trimethylsiloxy) silylstyrene and bis (trimethylsiloxy).
Methylsilylstyrene, dimethylsilylstyrene, trimethylsilylstyrene, tris (trimethylsiloxy)
Siloxanyldimethylsilylstyrene, [bis (trimethylsiloxy) methylsiloxanyl] dimethylsilylstyrene, pentamethyldisiloxanylstyrene, heptamethyltrisiloxanylstyrene, nonamethyltetrasiloxanylstyrene, pentadecamethylhepta Siloxanyl styrene, hene eicosamethyl decasiloxanyl styrene, heptacosamethyl trideca siloxanyl styrene, hentriacontamethyl pentadeca siloxanyl styrene, trimethylsiloxypentamethyldisiloxymethylsilylstyrene, tris (pentamethyl Disiloxy) silylstyrene, (tristrimethylsiloxy) siloxanyl bis (trimethylsiloxy) silylstyrene, bis (heptamethyltrisiloxy) methylsilylstyrene, tris (methyl) Bistrimethylsiloxysiloxy) silylstyrene, trimethylsiloxybis (tristrimethylsiloxysiloxy) silylstyrene, heptakis (trimethylsiloxy) trisiloxanylstyrene, tris (tristrimethylsiloxysiloxy) silylstyrene, (tristrimethylsiloxyhexamethyl) tetrasiloxy (Tristrimethylsiloxy) siloxytrimethylsiloxysilylstyrene, nonakis (trimethylsiloxy) tetrasiloxanylstyrene, bis (tridecamethylhexasiloxy) methylsilylstyrene, heptamethylcyclotetrasiloxanylstyrene,
Examples thereof include heptamethylcyclotetrasiloxybis (trimethylsiloxy) silylstyrene and tripropyltetramethylcyclotetrasiloxanylstyrene.

Examples of the alkyl vinyl silane include trimethyl vinyl silane and the like.

Among the above-mentioned silicon-containing monomers, tris (trimethylsiloxy) silylpropyl () is excellent in compatibility with other polymerization components and has a great effect of improving oxygen permeability of the obtained ophthalmic lens material. (Meth) acrylate and tris (trimethylsiloxy)
Silyl styrene is particularly preferred.

The above-mentioned silicon-containing monomers may be used alone or in combination of two or more kinds, and the content thereof may be appropriately adjusted according to the properties of the intended eye lens material. For example, when trying to obtain an ophthalmic lens material having a low water content and a high oxygen permeability, the content of the silicon-containing monomer should be the total amount of the polymerization components in order to sufficiently express the effect of improving the oxygen permeability. Of 5% by weight or more, preferably 10% by weight or more, more preferably 20% by weight or more, and in order to eliminate the possibility of decreasing the compatibility with other polymerization components, 70% by weight or less of the total amount of the components, preferably 60% by weight or less,
It is more desirable to adjust the content to 50% by weight or less.

When it is desired to further improve the hydrophilicity of the obtained ophthalmic lens material to impart water content to the ophthalmic lens material, for example, a hydroxyl group, an amide group, a carboxyl group, an amino group, or a glycol residue is left. A hydrophilic monomer having a group, a pyrrolidone skeleton, a morpholino skeleton, or the like is used.

Examples of the hydrophilic monomer include 2
-Hydroxyethyl (meth) acrylate, hydroxybutyl (meth) acrylate, hydroxypropyl (meth) acrylate and other hydroxyalkyl (meth) acrylates; 2-dimethylaminoethyl (meth) acrylate, 2-butylaminoethyl (meth) acrylate, etc. (Alkyl) aminoalkyl (meth) acrylate; alkyl (meth) acrylamide such as N, N-dimethyl (meth) acrylamide; polyglycol mono (meth) acrylate such as propylene glycol mono (meth) acrylate; vinylpyrrolidone; ) Acrylic acid; maleic anhydride; fumaric acid; fumaric acid derivatives; aminostyrene; hydroxystyrene; general formula (VI
I):

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(In the formula, R ⁸ is a hydrogen atom or a methyl group,
u represents an integer of 1 to 12) and the like.

In the general formula (VII) representing the morpholino compound, u is an integer of 1 to 12. When u is an integer larger than 12, the alkylene chain becomes long and the hydrophobicity is high. There is a tendency that the amount of the hydrophilic moiety increases too much, and the effect of imparting hydrophilicity by the morpholino compound is not sufficiently exhibited.

Representative examples of the morpholino compound include:
Examples thereof include morpholinomethyl (meth) acrylate and morpholinoethyl (meth) acrylate.

Among the above-mentioned hydrophilic monomers, alkyl (meth) acrylamide, (meth) are preferable because they are excellent in compatibility with other polymerization components and have a great effect of improving hydrophilicity of the obtained ophthalmic lens material. Acrylic acid and hydroxyalkyl (meth) acrylate are especially preferred.

Further, since the morpholino compound imparts appropriate hydrophilicity to the obtained ophthalmic lens material and has excellent compatibility with a hydrophobic component, particularly a silicon-containing hydrophobic component, the hydrophobic component is Even when mixed with and polymerized, the obtained polymer does not become cloudy,
It is preferable because it has excellent transparency.

Further, when the morpholino compound is used, the ophthalmic lens material is provided with appropriate hydrophilicity.
Even when the obtained ophthalmic lens material is, for example, a non-water-containing material, it becomes difficult for hydrophobic stains such as lipids to adhere, and by adjusting the content of the morpholino compound appropriately, There is also an advantage that it can be used as a material having good properties.

The above hydrophilic monomers may be used alone or in combination of two or more, and the content thereof may be appropriately adjusted depending on the properties of the intended ophthalmic lens material. For example, in order to obtain an ophthalmic lens material having high oxygen permeability, the content of the hydrophilic monomer should be the same as that of the polymerization component in order to sufficiently exert the effect of improving hydrophilicity and the effect of imparting water content. It is desirable to adjust the total amount to 5% by weight or more, preferably 10% by weight or more, more preferably 20% by weight or more, and eliminate the risk that the water content of the obtained ophthalmic lens material becomes too high. In order to achieve this, 80% by weight or less of the total amount of the polymerization components, preferably 7
It is desirable to adjust the content to be 5% by weight or less, more preferably 70% by weight or less.

Further, in order to improve the mechanical strength and durability of the obtained ophthalmic lens material and impart water resistance and solvent resistance to the ophthalmic lens material, a copolymerizable unsaturated monomer is used. It is preferable to use a crosslinkable monomer that is a polyfunctional polymerizable compound having two or more double bonds.

Examples of the crosslinkable monomer include ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, dipropylene glycol di (meth). Acrylate, allyl (meth) acrylate,
Vinyl (meth) acrylate, trimethylolpropane tri (meth) acrylate, methacryloyloxyethyl acrylate, divinylbenzene, diallyl phthalate, diallyl adipate, triallyl isocyanurate, α-methylene-N-vinylpyrrolidone, 4-vinylbenzyl (meta ) Acrylate, 3-vinylbenzyl (meth) acrylate, 2,2-bis (p- (meth) acryloyloxyphenyl) hexafluoropropane,
2,2-bis (m- (meth) acryloyloxyphenyl) hexafluoropropane, 2,2-bis (o- (meth) acryloyloxyphenyl) hexafluoropropane, 2,2-bis (p- (meth) acryloyl Oxyphenyl) propane, 2,2-bis (m- (meth) acryloyloxyphenyl) propane, 2,2-bis (o-
(Meth) acryloyloxyphenyl) propane, 1,
4-bis (2- (meth) acryloyloxyhexafluoroisopropyl) benzene, 1,3-bis (2- (meth) acryloyloxyhexafluoroisopropyl)
Benzene, 1,2-bis (2- (meth) acryloyloxyhexafluoroisopropyl) benzene, 1,4-
Bis (2- (meth) acryloyloxyisopropyl)
Examples thereof include benzene, 1,3-bis (2- (meth) acryloyloxyisopropyl) benzene, and 1,2-bis (2- (meth) acryloyloxyisopropyl) benzene.

Among the above-mentioned crosslinkable monomers, ethylene glycol di (meth) acrylate is preferable because it has excellent compatibility with other polymerization components and has a great effect of improving the mechanical strength of the obtained ophthalmic lens material. Especially preferred.

The crosslinkable monomers may be used alone or in combination of two or more, and the content thereof may be appropriately adjusted according to the properties of the intended ophthalmic lens material. For example, when trying to obtain an ophthalmic lens material having low water content and high oxygen permeability, in order to sufficiently exhibit the effect of improving mechanical strength, durability, water resistance, solvent resistance, etc., The content of the crosslinkable monomer is 0.0 of the total amount of the polymerization components.
It is desirable to adjust the amount to be 1% by weight or more, preferably 0.05% by weight or more, and more preferably 0.1% by weight or more. In order to eliminate the risk of the ophthalmic lens material becoming brittle, a polymerization component is used. It is desirable to adjust the total amount to 10% by weight or less, preferably 5% by weight or less, and more preferably 3% by weight or less.

Further, in order to impart stain resistance to the obtained ophthalmic lens material, a fluorine-containing monomer which is a polymerizable compound in which a part of hydrogen atoms of a hydrocarbon group is substituted with fluorine atoms. Are used.

Examples of the fluorine-containing monomer include, for example, general formula (VIII): CH ₂ ═CR ⁹ COOC _a H _{(2a-b-c + 1)} F _b (OH) _c (VIII) (wherein R ⁹ is Hydrogen atom or methyl group, a is 1 to 15
, B is an integer of 1 to (2a + 1), and c is an integer of 0 to 2).

Typical examples of the monomer represented by the general formula (VIII) include 2,2,2-trifluoroethyl (meth) acrylate, 2,2,3,3-tetrafluoropropyl (meth) acrylate, 2, 2, 3,
3-tetrafluoro-t-pentyl (meth) acrylate, 2,2,3,4,4,4-hexafluorobutyl (meth) acrylate, 2,2,3,4,4,4-hexafluoro-t- Hexyl (meth) acrylate, 2,
3,4,5,5,5-hexafluoro-2,4-bis (trifluoromethyl) pentyl (meth) acrylate, 2,2,3,3,4,4-hexafluorobutyl (meth) acrylate, 2 , 2,2,2 ', 2', 2 '
-Hexafluoroisopropyl (meth) acrylate,
2,2,3,3,4,4,4-heptafluorobutyl (meth) acrylate, 2,2,3,3,4,4,5,
5-octafluoropentyl (meth) acrylate,
2,2,3,3,4,4,5,5,5-nonafluoropentyl (meth) acrylate, 2,2,3,3,4
4,5,5,6,6,7,7-dodecafluoroheptyl (meth) acrylate, 3,3,4,4,5,5,6
6,7,7,8,8-dodecafluorooctyl (meth)
Acrylate, 3,3,4,4,5,5,6,6,7,
7,8,8,8-tridecafluorooctyl (meth) acrylate, 2,2,3,3,4,4,5,5,6
6,7,7,7-tridecafluoroheptyl (meth) acrylate, 3,3,4,4,5,5,6,6,7,
7,8,8,9,9,10,10-hexadecafluorodecyl (meth) acrylate, 3,3,4,4,5
5,6,6,7,7,8,8,9,9,10,10,1
0-heptadecafluorodecyl (meth) acrylate,
3,3,4,4,5,5,6,6,7,7,8,8,
9,9,10,10,11,11-octadecafluoroundecyl (meth) acrylate, 3,3,4,4,
5,5,6,6,7,7,8,8,9,9,10,1
0,11,11,11-nonadecafluoroundecyl (meth) acrylate, 3,3,4,4,5,5,6
6,7,7,8,8,9,9,10,10,11,1
1,12,12-eicosafluorododecyl (meth) acrylate, 2-hydroxy-4,4,5,5,6
7,7,7-octafluoro-6-trifluoromethylheptyl (meth) acrylate, 2-hydroxy-4,
4,5,5,6,6,7,7,8,9,9,9-dodecafluoro-8-trifluoromethylnonyl (meth) acrylate, 2-hydroxy-4,4,5,5,6 6,
7, 7, 8, 8, 9, 9, 10, 11, 11, 11-hexadecafluoro-10-trifluoromethylundecyl (meth) acrylate and the like.

Among the above-mentioned fluorine-containing monomers, 2,2,2-trifluoroethyl (meth) acrylate and 2,2,2 are preferred because they are highly effective in improving the stain resistance of the obtained ophthalmic lens material. , 2 ', 2', 2 '
-Hexafluoroisopropyl (meth) acrylate is particularly preferred.

The above-mentioned fluorine-containing monomers can be used alone or in combination of two or more, and the content thereof is
It may be appropriately adjusted according to the intended properties of the ophthalmic lens material. For example, when trying to obtain an ophthalmic lens material having low water content and high oxygen permeability, the content of the fluorine-containing monomer should be the total amount of the polymerization components in order to sufficiently exhibit the effect of improving the stain resistance. Of 1% by weight or more, preferably 3% by weight or more, more preferably 5% by weight or more, and in order to eliminate the possibility of decreasing the compatibility with other polymerization components, 30 of all ingredients
It is desirable to adjust the content to be not more than 20% by weight, preferably not more than 20% by weight, more preferably not more than 15% by weight.

For example, in order to adjust the hardness of the obtained ophthalmic lens material to impart hardness or softness, for example, alkyl (meth) acrylates, which are polymerizable compounds having an alkyl group, alkyl Styrenes and hardness adjusting monomers such as styrene are used.

Examples of the alkyl (meth) acrylates include methyl (meth) acrylate, ethyl (meth) acrylate, isopropyl (meth) acrylate, n-propyl (meth) acrylate, isobutyl (meth) acrylate, n-butyl ( (Meth) acrylate, 2-ethylhexyl (meth) acrylate, n-octyl (meth) acrylate, n-decyl (meth) acrylate, n-dodecyl (meth) acrylate, t-butyl (meth) acrylate, pentyl (meth) acrylate, t-pentyl (meth) acrylate, hexyl (meth) acrylate, heptyl (meth) acrylate, nonyl (meth) acrylate, stearyl (meth)
Acrylate, cyclopentyl (meth) acrylate,
Linear, branched or cyclic alkyl (meth) acrylates such as cyclohexyl (meth) acrylate; for example, 2-ethoxyethyl (meth) acrylate, 3-
Alkoxyalkyl (meth) acrylates such as ethoxypropyl (meth) acrylate, 2-methoxyethyl (meth) acrylate, and 3-methoxypropyl (meth) acrylate; for example, ethylthioethyl (meth)
Examples include acrylates and alkylthioalkyl (meth) acrylates such as methylthioethyl (meth) acrylate.

Examples of the alkyl styrenes include α-methyl styrene; alkyl styrenes such as methyl styrene, ethyl styrene, propyl styrene, butyl styrene, t-butyl styrene, isobutyl styrene and pentyl styrene; methyl-α-methyl styrene; Alkyl-α-methyl such as ethyl-α-methylstyrene, propyl-α-methylstyrene, butyl-α-methylstyrene, t-butyl-α-methylstyrene, isobutyl-α-methylstyrene and pentyl-α-methylstyrene. Examples include styrene.

Among the hardness adjusting monomers,
For example, when a soft contact lens or the like is to be obtained, a homopolymer having a glass transition temperature (hereinafter referred to as Tg) of 40 ° C. or lower is preferably used. Further, for example, when a hard contact lens is to be obtained, a homopolymer having a Tg higher than 40 ° C. is preferably used. Furthermore, alkyl (meth) acrylates and alkylstyrenes are particularly preferred in that they have excellent compatibility with other polymerization components and copolymerizability.

The hardness adjusting monomer may be used alone or in combination with 2.
A mixture of two or more species may be used, and the content thereof may be appropriately adjusted according to the properties of the intended ophthalmic lens material. For example, when an ophthalmic lens material having a low water content and a high oxygen permeability is to be obtained, the content of the hardness adjusting monomer is set to the total amount of the polymerization components in order to sufficiently exert the effect of adjusting the hardness. 1% by weight or more, preferably 3% by weight
As described above, it is preferable to adjust the content to be 5% by weight or more, and the content of other polymerization components such as a silicon-containing compound is relatively small. For example, oxygen permeability, hydrophilicity, transparency, etc. In order to eliminate the possibility that the improvement effect of 1) is not sufficiently exhibited, it is desirable to adjust the content to 80% by weight or less, preferably 75% by weight or less, and more preferably 70% by weight or less of the total amount of the polymerization component.

When the obtained ophthalmic lens material is to be provided with ultraviolet absorptivity or when the ophthalmic lens material is to be colored, for example, a polymerizable ultraviolet absorber, a polymerizable dye, a polymerizable ultraviolet absorptivity is used. A dye or the like is used.

As typical examples of the polymerizable ultraviolet absorber, for example, 2-hydroxy-4- (meth) acryloyloxybenzophenone, 2-hydroxy-4- (meth) acryloyloxy-5-t-butylbenzophenone, 2- Benzophenone-based polymerizable UV absorption such as hydroxy-4- (meth) acryloyloxy-2 ', 4'-dichlorobenzophenone and 2-hydroxy-4- (2'-hydroxy-3'-(meth) acryloyloxypropoxy) benzophenone Agent; 2- (2'-hydroxy-5 '-(meth) acryloyloxyethylphenyl)
-2H-benzotriazole, 2- (2'-hydroxy-5 '-(meth) acryloyloxyethylphenyl)
-5-chloro-2H-benzotriazole, 2- (2 '
-Hydroxy-5 '-(meth) acryloyloxypropylphenyl) -2H-benzotriazole, 2-
Benzotriazole polymerizable ultraviolet absorbers such as (2'-hydroxy-5 '-(meth) acryloyloxypropyl-3'-t-butylphenyl) -5-chloro-2H-benzotriazole; 2-hydroxy-4- Salicylic acid derivative-based polymerizable ultraviolet absorbers such as phenyl methacryloyloxymethylbenzoate; other 2-cyano-3-
Polymerizable ultraviolet absorbers such as phenyl-3- (3 '-(meth) acryloyloxyphenyl) propenyl acid methyl ester, etc., and these can be used alone or in combination of two or more.

Typical examples of the polymerizable dyes include 1-phenylazo-4- (meth) acryloyloxynaphthalene and 1-phenylazo-2-hydroxy-3-.
(Meth) acryloyloxynaphthalene, 1-naphthylazo-2-hydroxy-3- (meth) acryloyloxynaphthalene, 1- (α-anthrylazo) -2-hydroxy-3- (meth) acryloyloxynaphthalene,
1-((4 '-(phenylazo) -phenyl) azo)-
2-Hydroxy-3- (meth) acryloyloxynaphthalene, 1- (2 ', 4'-xylylazo) -2- (meth) acryloyloxynaphthalene, 1- (o-tolylazo) -2- (meth) acryloyloxynaphthalene ,
2- (m- (meth) acryloylamide-anilino)-
4,6-bis (1 '-(o-tolylazo) -2'-naphthylamino) -1,3,5-triazine, 2- (m-vinylanilino) -4- (4'-nitrophenylazo)-
Anilino) -6-chloro-1,3,5-triazine, 2
-(1 '-(o-tolylazo) -2'-naphthyloxy) -4- (m-vinylanilino) -6-chloro-1,
3,5-triazine, 2- (p-vinylanilino) -4
-(1 '-(o-tolylazo) -2'naphthylamino)
-6-chloro-1,3,5-triazine, N- (1'-
(O-tolylazo) -2'-naphthyl) -3-vinylphthalic acid monoamide, N- (1 '-(o-tolylazo)-
2'-naphthyl) -6-vinylphthalic acid monoamide, 3
-Vinylphthalic acid- (4 '-(p-sulfophenylazo) -1'-naphthyl) monoester, 6-vinylphthalic acid- (4'-(p-sulfophenylazo) -1'-naphthyl) monoester, 3 -(Meth) acryloylamide-4-phenylazophenol, 3- (meth) acryloylamide-4- (8'-hydroxy-3 ', 6'-
Disulfo-1'-naphthylazo) -phenol, 3-
(Meth) acryloylamido-4- (1'-phenylazo-2'-naphthylazo) -phenol, 3- (meth)
Acryloylamide-4- (p-tolylazo) -phenol, 2-amino-4- (m- (2'-hydroxy-
1'-naphthylazo) anilino) -6-isopropenyl-1,3,5-triazine, 2-amino-4- (N-methyl-p- (2'-hydroxy-1'-naphthylazo)
Anilino) -6-isopropenyl-1,3,5-triazine, 2-amino-4- (m- (4'-hydroxy-
1'-phenylazo) anilino) -6-isopropenyl-1,3,5-triazine, 2-amino-4- (N-methyl-p- (4'-hydroxyphenylazo) anilino) -6-isopropenyl- 1,3,5-triazine,
2-amino-4- (m- (3'-methyl-1'-phenyl-5'-hydroxy-4'-pyrazolylazo) anilino) -6-isopropenyl-1,3,5-triazine,
2-Amino-4- (N-methyl-p- (3'-methyl-
1'-phenyl-5'-hydroxy-4'-pyrazolylazo) anilino) -6-isopropenyl-1,3,5-
Azo-based polymerization such as triazine, 2-amino-4- (p-phenylazoanilino) -6-isopropenyl-1,3,5-triazine, 4-phenylazo-7- (meth) acryloylamide-1-naphthol Sex dye; 1,5-
Bis ((meth) acryloylamino) -9,10-anthraquinone, 1- (4'-vinylbenzoylamide)-
9,10-anthraquinone, 4-amino-1- (4'-
Vinyl benzoylamide) -9,10-anthraquinone, 5-amino-1- (4'-vinylbenzoylamide) -9,10-anthraquinone, 8-amino-1-
(4'-vinylbenzoylamide) -9,10-anthraquinone, 4-nitro-1- (4'-vinylbenzoylamide) -9,10-anthraquinone, 4-hydroxy-1- (4'-vinylbenzoylamide) -9,10-
Anthraquinone, 1- (3'-vinylbenzoylamide) -9,10-anthraquinone, 1- (4'-isopropenylbenzoylamide) -9,10-anthraquinone, 1- (3'-isopropenylbenzoylamide)-
9,10-anthraquinone, 1- (2'-isopropenylbenzoylamide) -9,10-anthraquinone,
1,4-bis (4'-vinylbenzoylamide) -9,
10-anthraquinone, 1,4-bis- (4'-isopropenylbenzoylamide) -9,10-anthraquinone, 1,5'-bis- (4'-vinylbenzoylamide) -9,10-anthraquinone, 5-bis-
(4'-isopropenylbenzoylamide) -9,10
-Anthraquinone, 1-methylamino-4- (3'-vinylbenzoylamide) -9,10-anthraquinone,
1-methylamino-4- (4'-vinylbenzoyloxyethylamino) -9,10-anthraquinone, 1-amino-4- (3'-vinylphenylamino) -9,10
-Anthraquinone-2-sulfonic acid, 1-amino-4-
(4'-Vinylphenylamino) -9,10-anthraquinone-2-sulfonic acid, 1-amino-4- (2'-vinylbenzylamino) -9,10-anthraquinone-2
-Sulfonic acid, 1-amino-4- (3 '-(meth) acryloylaminophenylamino) -9,10-anthraquinone-2-sulfonic acid, 1-amino-4- (3'-
(Meth) acryloylaminobenzylamino) -9,1
0-anthraquinone-2-sulfonic acid, 1- (β-ethoxycarbonylallylamino) -9,10-anthraquinone, 1- (β-carboxyallylamino) -9,10
-Anthraquinone, 1,5-di- (β-carboxyallylamino) -9,10-anthraquinone, 1,5-di-
(Β-isopropoxycarbonylallylamino) -5
Benzoylamide-9,10-anthraquinone, 2-
(3 '-(meth) acryloylamide-anilino) -4
-(3 '-(3 "-sulfo-4" -aminoanthraquinone-1 "-yl) -amino-anilino) -6-chloro-
1,3,5-triazine, 2- (3 '-(meth) acryloylamide-anilino) -4- (3'-(3 "-sulfo-4" -aminoanthraquinone-1 "-yl) -amino-anilino ) -6-Hydrazino-1,3,5-triazine, 2,4-bis-((4 "-methoxyanthraquinone-1" -yl) -amino) -6- (3'-vinylanilino) -1,3, 5-triazine, 2- (2'-vinylphenoxy) -4- (4 '-(3 "-sulfo-4" -aminoanthraquinone-1 "-yl-amino) -anilino) -6-chloro-1,3 Anthraquinone-based polymerizable dyes such as 1,5-triazine; nitro-based polymerizable dyes such as o-nitroanilinomethyl (meth) acrylate; (meth) acryloylated tetraamino copper phthalocyanine;
Examples include phthalocyanine-based polymerizable dyes such as (meth) acryloylated (dodecanoylated tetraamino copper phthalocyanine), and these can be used alone or in combination of two or more.

Typical examples of the polymerizable ultraviolet absorbing dyes include 2,4-dihydroxy-3 (p-styrenoazo) benzophenone and 2,4-dihydroxy-5-.
(P-stylenoazo) benzophenone, 2,4-dihydroxy-3- (p- (meth) acryloyloxymethylphenylazo) benzophenone, 2,4-dihydroxy-5- (p- (meth) acryloyloxymethylphenylazo) benzophenone , 2,4-dihydroxy-3-
(P- (meth) acryloyloxyethylphenylazo) benzophenone, 2,4-dihydroxy-5- (p
-(Meth) acryloyloxyethylphenylazo) benzophenone, 2,4-dihydroxy-3- (p- (meth) acryloyloxypropylphenylazo) benzophenone, 2,4-dihydroxy-5- (p- (meth)
Acryloyloxypropylphenylazo) benzophenone, 2,4-dihydroxy-3- (o- (meth) acryloyloxymethylphenylazo) benzophenone,
2,4-dihydroxy-5- (o- (meth) acryloyloxymethylphenylazo) benzophenone, 2,4
-Dihydroxy-3- (o- (meth) acryloyloxyethylphenylazo) benzophenone, 2,4-dihydroxy-5- (o- (meth) acryloyloxyethylphenylazo) benzophenone, 2,4-dihydroxy-3- ( o- (meth) acryloyloxypropylphenylazo) benzophenone, 2,4-dihydroxy-
5- (o- (meth) acryloyloxypropylphenylazo) benzophenone, 2,4-dihydroxy-3-
(P- (N, N-di (meth) acryloyloxyethylamino) phenylazo) benzophenone, 2,4-dihydroxy-5- (p- (N, N-di (meth) acryloyloxyethylamino) phenylazo) benzophenone, 2,4-dihydroxy-3- (o- (N, N-di (meth) acryloyloxyethylamino) phenylazo) benzophenone, 2,4-dihydroxy-5- (o
-(N, N-di (meth) acryloyloxyethylamino) phenylazo) benzophenone, 2,4-dihydroxy-3- (p- (N-ethyl-N- (meth) acryloyloxyethylamino) phenylazo) benzophenone, 2 , 4-dihydroxy-5- (p- (N-ethyl-
N-di (meth) acryloyloxyethylamino) phenylazo) benzophenone, 2,4-dihydroxy-3
-(O- (N-ethyl-N- (meth) acryloyloxyethylamino) phenylazo) benzophenone, 2,
4-dihydroxy-5- (o- (N-ethyl-N-di (meth) acryloyloxyethylamino) phenylazo) benzophenone, 2,4-dihydroxy-3- (p
-(N-ethyl-N- (meth) acryloylamino) phenylazo) benzophenone, 2,4-dihydroxy-
5- (p- (N-ethyl-N-di (meth) acryloylamino) phenylazo) benzophenone, 2,4-dihydroxy-3- (o- (N-ethyl-N- (meth) acryloylamino) phenylazo) benzophenone , 2,
Benzophenone-based polymerizable ultraviolet absorbing dyes such as 4-dihydroxy-5- (o- (N-ethyl-N-di (meth) acryloylamino) phenylazo) benzophenone and 2-hydroxy-4- (p-styrenoazo) benzoic acid Examples thereof include benzoic acid-based polymerizable ultraviolet absorbing dyes such as phenyl acid, and these can be used alone or in admixture of two or more.

The contents of the polymerizable ultraviolet absorber, the polymerizable dye, and the polymerizable ultraviolet absorbent dye may be appropriately adjusted according to the properties of the target ophthalmic lens material, but the amount is large depending on the thickness of the lens. Therefore, the amount is preferably 3% by weight or less of the total amount of the polymerization components, and more preferably 0.
1 to 2% by weight. When the content is more than the upper limit, the physical properties of the ophthalmic lens material, such as mechanical strength tends to be reduced, and in consideration of the toxicity of the ultraviolet absorber and the dye, in the biological tissue. It tends to be unsuitable as a material for ophthalmic lenses such as contact lenses that come into direct contact and intraocular lenses that are embedded in a living body.
In addition, especially in the case of a dye, if the content is too large, the color of the lens becomes too dark and the transparency is lowered, so that the lens tends to be difficult to transmit visible light.

In the present invention, among the polymerizable monomers, one or more kinds of monomers other than the polysiloxane macromonomer are selected as a macromonomer, which is one of the polymerizable monomers. May be contained in the polymerization component.

The polymerization component containing the above-mentioned silicon-containing compound and optionally a polymerizable monomer is appropriately adjusted according to the intended use of the ophthalmic lens such as a contact lens or an intraocular lens, and then provided for polymerization. To be

In the present invention, a polymerization component containing a silicon-containing compound and, if necessary, a polymerizable monomer is adjusted to a desired amount within the above-mentioned contents, and a radical polymerization initiator is added thereto. A polymer can be obtained by polymerizing by a usual method.

The above-mentioned ordinary method means, for example, after adding a radical polymerization initiator, gradually heating in a temperature range of room temperature to about 130 ° C. (heat polymerization), microwave, ultraviolet ray,
This is a method of polymerizing by irradiating electromagnetic waves such as radiation (γ rays). In the case of heat polymerization, the temperature may be raised stepwise. The polymerization may be performed by a bulk polymerization method, a solution polymerization method using a solvent or the like, or may be performed by another method.

As typical examples of the radical polymerization initiator, for example, azobisisobutyronitrile, azobisdimethylvaleronitrile, benzoyl peroxide, t
-Butyl hydroperoxide, cumene hydroperoxide and the like, and these can be used alone or in combination of two or more. In the case where the polymerization is carried out using a light beam or the like, it is preferable to further add a photopolymerization initiator or a sensitizer. The amount of the polymerization initiator or sensitizer blended is about 0.001 to 2 parts, especially 0.0
It is preferably 1 to 1 part.

When the ophthalmic lens material of the present invention is molded as an ophthalmic lens such as a contact lens or an intraocular lens, a molding method usually practiced by those skilled in the art can be adopted. Examples of such a molding method include a cutting method and a mold method. The cutting method is
Polymerization is carried out in an appropriate mold or container to obtain a rod-shaped, block-shaped, or plate-shaped material (polymer), and then the material is processed into a desired shape by mechanical processing such as cutting or polishing. Further, the mold method is a method in which a mold corresponding to the shape of a desired ophthalmic lens is prepared, a polymerization product is obtained by polymerizing the above-mentioned polymerization components in the mold, and mechanically finishing is performed if necessary. Is. Furthermore, a method combining these cutting method and casting method can also be adopted.

When the ophthalmic lens material of the present invention is used as a soft material at a temperature near room temperature, it is generally preferable to adopt a molding method by a molding method when molding the ophthalmic lens. . Such a casting method includes, for example, a spin casting method and a static casting method.

In addition to these methods, for example, a soft ophthalmic lens material is impregnated with a monomer that gives a hard polymer, and then the monomer is polymerized to harden the whole body, followed by cutting to obtain a desired polymer. A method of removing a hard polymer from a molded product processed into the above shape to obtain a molded product (ophthalmic lens) made of a soft material (JP-A-62-1780)
No. 241, Japanese Patent Application Laid-Open No. 1-111854), etc.
It can be preferably applied to the present invention.

Further, when the intraocular lens is loosened, the supporting portion of the lens may be manufactured separately from the lens and attached to the lens later, or may be molded (integrally) with the lens at the same time. There is no particular limitation.

The thus-obtained ophthalmic lens material of the present invention comprises a polymer obtained by polymerizing a polymerization component containing a silicon-containing compound represented by the general formula (I). Since it has excellent properties and transparency and has appropriate hydrophilicity, it can be suitably used for ophthalmic lenses such as contact lenses, intraocular lenses and artificial corneas.

[0122]

EXAMPLES Next, the ophthalmic lens material of the present invention will be described in more detail based on examples, but the present invention is not limited to these examples.

Production Example 1 (Synthesis of N-tris (trimethylsiloxy) silylpropyl methacryloxyethyl carbamate) Water was mixed in a 1 liter three-necked flask equipped with a reflux condenser, a thermometer, a dropping funnel and a stirrer. 50 g of 2-hydroxyethyl methacrylate without
(About 0.4 mol) and dibutyltin dilaurate 1.2
g, and while maintaining the temperature at 30 to 40 ° C., tris (trimethylsiloxy) silylpropyl isocyanate 76 g
(About 0.2 mol) was added dropwise, and the mixture was stirred at the same temperature for 16 hours.

Next, the unreacted 2-hydroxyethyl methacrylate was washed with a separating funnel and washed with water, and vacuum dried to obtain 70 g of a colorless transparent liquid product (yield: 84%).

The infrared absorption spectrum of the obtained product was measured by the KBr liquid film method using FT-IR8300 manufactured by JASCO Corporation. The result is shown in FIG. 1 as the infrared transmittance (%).

From the results shown in FIG. 1, 3400 cm ^-1
And a urethane bond (-OCON around 1750 cm ^-1
H-) absorption based on Si-O- near 1058 cm ^-1
Absorption based on Si, (CH ₃ ) ₃ -S near 843 cm ^-1
It can be seen that absorption based on iO- is observed respectively.

Further, regarding the obtained product, Vari
superconducting FT-NMR GEMINI 200 manufactured by an company
¹ H-nuclear magnetic resonance spectrum was measured using 0/400. The result is shown in FIG.

From the results shown in FIG. 2, 0.15 ppm
A signal attributed to —Si (CH ₃ ) ₃ in the vicinity (in FIG. 2,
Peak of (a)), 0.41ppm, -C 3 H 6 around 1.58ppm and 3.15 ppm - (in FIG. 2, (b) signal was assigned to the peak of), in the vicinity of 4.81 ppm -NH- 2 (peak of (c) in FIG. 2), a signal attributable to —C ₂ H ₄ — (peak of (d) in FIG. 2) in the vicinity of 4.30 ppm, 5.59 ppm and 6.18 ppm Signal assigned to = CH ₂ in the vicinity (peak of (e) in FIG. 2), in the vicinity of 1.98 ppm
It can be seen that signals attributed to C (CH ₃ ) = (peak of (f) in FIG. 2) are respectively observed.

Further, the obtained product was subjected to mass spectrum measurement by GC-MS (5890II gas chromatograph) manufactured by Hewlett-Packard Company. The result is shown in FIG.

The attributions of the peaks (1) to (4) shown in FIG. 3 are as follows.

[0131]

Embedded image

From these results, the product obtained is
formula:

[0133]

Embedded image

It was confirmed to be N-tris (trimethylsiloxy) silylpropyl methacryloxyethyl carbamate represented by:

Production Example 2 (Synthesis of N-tris (trimethylsiloxy) silylpropylacryloxyethyl carbamate) In Production Example 1, 50 g of 2-hydroxyethyl acrylate was used instead of 50 g (about 0.4 mol) of 2-hydroxyethyl methacrylate. A colorless and transparent liquid product 70 in the same manner as in Production Example 1 except that (about 0.4 mol) was used.
g was obtained (yield: 83%).

The infrared absorption spectrum of the obtained product was measured in the same manner as in Production Example 1. The results are shown in FIG. 4 as the infrared transmittance (%).

From the results shown in FIG. 4, 3400 cm ^-1
And a urethane bond (-OCON around 1750 cm ^-1
H-) absorption based on Si-O-in the vicinity of 1054 cm ^-1
Absorption based on Si, (CH ₃ ) ₃ -S near 843 cm ^-1
It can be seen that absorption based on iO- is observed respectively.

Further, with respect to the obtained product, Production Example 1
¹ H-nuclear magnetic resonance spectrum was measured in the same manner as in.
The result is shown in FIG.

From the results shown in FIG. 5, 0.15 ppm
A signal attributed to —Si (CH ₃ ) ₃ in the vicinity (in FIG. 5,
Peak of (a)), 0.41ppm, -C 3 H 6 around 1.58ppm and 3.15 ppm - (in FIG. 5, (b) signal was assigned to the peak of), in the vicinity of 4.81 ppm -NH- 5 (peak of (c) in FIG. 5), signal attributed to —C ₂ H ₄ — (peak of (d) in FIG. 5) near 4.30 ppm, 5.83 ppm and 6.18 ppm A signal attributed to = CH ₂ in the vicinity (peak of (e) in FIG. 5), and −6.45 ppm in the vicinity.
Signal attributed to CH = (peak of (f) in FIG. 5)
It can be seen that each is recognized.

Further, the mass spectrum of the obtained product was measured in the same manner as in Production Example 1. FIG. 6 shows the result.

The attributions of the peaks (1) to (4) shown in FIG. 6 are as follows.

[0142]

Embedded image

From these results, the product obtained is
formula:

[0144]

Embedded image

It was confirmed to be N-tris (trimethylsiloxy) silylpropylacryloxyethyl carbamate represented by:

Example 1 (Preparation of Polymer) 100 parts of N-tris (trimethylsiloxy) silylpropylmethacryloxyethylcarbamate obtained in Preparation Example 1 as a polymerization component and 0.3 part of ethylene glycol dimethacrylate were used to initiate polymerization. After mixing with 0.1 part of 2,2'-azobis (2,4-dimethylvaleronitrile) as an agent, the obtained mixture was transferred into a test tube, and the reaction system was replaced with nitrogen and sealed.

Next, the tightly stoppered test tube was placed in a circulating constant temperature water tank, polymerization was carried out at 35 ° C. for 40 hours and at 50 ° C. for 8 hours, and the test tube was transferred to a circulating drier for 2 hours. 14 at 60 to 120 ° C while increasing the temperature by 10 ° C
The mixture was heated at 110 ° C. for 2 hours to complete the polymerization to obtain a colorless transparent polymer.

The obtained polymer was mechanically processed by cutting and polishing to prepare a test piece having a diameter of 15 mm and a thickness of 0.2 mm. At this time, the processability of the polymer was good.

When the obtained test piece was visually observed, it was transparent without clouding and had no optical distortion, and it was suitable for use as an ophthalmic lens material, for example.

Further, the test piece was further subjected to cutting and polishing to produce a contact lens. Both the cut surface and the polished surface of the contact lens were good.

Next, the oxygen permeability coefficient and contact angle of the test piece were measured according to the following methods. Table 1 shows the results.

(A) Oxygen permeability coefficient (DK _0.2 ) The oxygen permeability coefficient of the test piece was measured in a physiological saline solution at 35 ° C. using a Seikaken film oxygen permeability meter manufactured by Rika Seiki Kogyo Co., Ltd. The unit of oxygen permeability coefficient is ml (S
TP) · cm ² / (cm ³ · sec · mmHg),
The oxygen permeability coefficient in Table 1 is a value obtained by multiplying the value of the oxygen permeability coefficient when the thickness of the test piece is 0.2 mm by 10 ¹¹ .

(B) Contact angle The contact angle (degree) was measured by the droplet method at a temperature of 25 ° C. using a goniometer.

Examples 2 to 11 and Comparative Example 1 A colorless and transparent polymer was obtained in the same manner as in Example 1 except that the polymerization components were changed as shown in Table 1.

A test piece was prepared from the obtained polymer in the same manner as in Example 1. At this time, the processability of the polymers of Examples 2 to 11 was good.

When the obtained test pieces were visually observed, the test pieces of Examples 2 to 11 were transparent without clouding and had no optical distortion, and were suitable for use as, for example, an ophthalmic lens material. It was

Further, the test piece was further subjected to cutting and polishing to produce a contact lens. Examples 2 to
Both the cut surface and the polished surface of the contact lens of No. 11 were good.

Next, the oxygen permeability coefficient and contact angle of the test piece were measured in the same manner as in Example 1. Table 1 shows the results.

The abbreviations in Table 1 indicate the following compounds.

TTMSSPMAEC: N-tris (trimethylsiloxy) silylpropyl methacryloxyethyl carbamate (compound synthesized in Preparation Example 1) TTMSSPAEC: N-tris (trimethylsiloxy) silylpropylacryloxyethylcarbamate (synthesized in Preparation Example 2) Compound) TTMSSPMA: tris (trimethylsiloxy) silylpropyl methacrylate DMAA: N, N-dimethylacrylamide MMA: methyl methacrylate BuA: n-butyl acrylate EDMA: ethylene glycol dimethacrylate

[0161]

[Table 1]

From the results shown in Table 1, the polymer (test piece) of Comparative Example 1 obtained using only the conventional silicon-containing methacrylate had a large oxygen permeability coefficient, but the contact angle was 120 degrees, which was extremely high. The polymers (test pieces) of Examples 1 to 11 obtained by using the silicon-containing compounds of Production Examples 1 and 2 are comparatively different in oxygen permeability coefficient, while they are large and significantly inferior in water wettability (hydrophilicity). It can be seen that the polymer is not so much inferior to the polymer of Example 1, has a small contact angle, and is excellent in water wettability (hydrophilicity).

[0163]

EFFECT OF THE INVENTION The ophthalmic lens material of the present invention has excellent oxygen permeability and transparency, and at the same time has an appropriate hydrophilicity, and also has, for example, releasability, shape stability, durability, slipperiness, and low abrasion resistance. It also has excellent antithrombotic properties. Therefore, the ophthalmic lens material of the present invention can be suitably used for contact lenses, intraocular lenses, artificial corneas, and the like.

[Brief description of the drawings]

FIG. 1 is a chart showing infrared ray transmittance of N-tris (trimethylsiloxy) silylpropyl methacryloxyethyl carbamate obtained in Production Example 1.

FIG. 2 is a ¹ H-nuclear magnetic resonance spectrum of N-tris (trimethylsiloxy) silylpropylmethacryloxyethylcarbamate obtained in Production Example 1.

FIG. 3 is a mass spectrum of N-tris (trimethylsiloxy) silylpropyl methacryloxyethyl carbamate obtained in Production Example 1.

FIG. 4 is a chart showing infrared ray transmittance of N-tris (trimethylsiloxy) silylpropylacryloxyethyl carbamate obtained in Production Example 2.

5 is a ¹ H-nuclear magnetic resonance spectrum of N-tris (trimethylsiloxy) silylpropylacryloxyethyl carbamate obtained in Production Example 2. FIG.

6 is a mass spectrum of N-tris (trimethylsiloxy) silylpropylacryloxyethyl carbamate obtained in Production Example 2. FIG.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification code Internal reference number FI Technical display location G02B 1/04 G02B 1/04 // C08F 20/10 MMJ C08F 20/10 MMJ 20/28 MMK 20 / 28 MMK 20/36 MMQ 20/36 MMQ (72) Inventor Shoji Ichinohe No. 1 Hitomi, Osamu Matsuida-cho, Usui-gun, Gunma Prefecture Shin-Etsu Chemical Co., Ltd. Silicone Electronic Materials Research Laboratory (72) Inventor Toshio Yamazaki Gunma No. 1 Hitomi, Oita, Matsuida-cho, Usui-gun, Japan 10 Shin-Etsu Chemical Co., Ltd. Silicone Electronic Materials Research Laboratory

Claims (5)

[Claims] 1. A compound of the general formula (I): (In the formula, R ¹ is an alkylene group having 1 to 6 carbon atoms, and A is a general formula (II): (In the formula, R ² is a hydrogen atom or a methyl group, and R ³ is a carbon atom 1
6 trivalent divalent hydrocarbon group having 1 to 6 carbon atoms when a hydrocarbon group or R ⁴ is a hydrogen atom, R ⁴ is a hydrogen atom, a hydroxyl group, an alkyl group or the formula 1 to 6 carbon atoms ( III): (In the formula, R ⁵ is an alkylene group having 1 to 6 carbon atoms, and m is 1 to
Represents an integer of 15) or represents a group represented by the formula) or a general formula (IV): (In the formula, R ⁶ represents a hydrogen atom or a methyl group, R ⁷ represents a direct bond or an alkylene group having 1 to 6 carbon atoms), and n represents an integer of 1 to 15). An ophthalmic lens material comprising a polymer obtained by polymerizing a polymerization component containing a compound. 2. The ophthalmic lens material according to claim 1, wherein the content of the silicon-containing compound is 5% by weight or more based on the total amount of the polymerization components. 3. The ophthalmic lens material according to claim 1, wherein the polymerization component contains a polymerizable monomer having an unsaturated double bond that is copolymerizable with a silicon-containing compound. 4. The ophthalmic lens material according to claim 3, wherein the polymerizable monomer having an unsaturated double bond copolymerizable with the silicon-containing compound is a crosslinkable monomer. 5. The ophthalmic lens material according to claim 4, wherein the content of the crosslinkable monomer is 0.01 to 10% by weight based on the total amount of the polymerization components.