JP2005089654A - Ocular lens material - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an ocular lens material which is transparent, has reduced tackiness, is safe without adsorption to the cornea on wearing, excels in operational ease, and furthermore excels in shape stability by an appropriate balance of strength and flexibility or elasticity. <P>SOLUTION: The ocular material is composed of a copolymer component comprising a compound (A) having an ethylenically unsaturated group and a group containing a polydimethylsiloxane structure through a urethane bond, an alkoxy group-containing acrylate (B) represented by formula (1) or formula (2), and a phenylalkyl acrylate or a phenoxyalkyl acrylate (C) represented by formula (3) (wherein X is oxygen or a direct bond), and has a stress in the tensile test at 35°C of 0.1-10 MPa, an elongation of 10-300%, and a Young's modulus of 0.4-3.0 MPa. <P>COPYRIGHT: (C)2005,JPO&NCIPI

Description

  The present invention relates to ophthalmic lens materials such as contact lenses and intraocular lenses, and more particularly to silicone-based non-hydrated ophthalmic lens materials. Furthermore, the present invention relates to a silicone-based non-hydrated contact lens material.

  In the case of a non-hydrous soft contact lens, if the surface becomes sticky in the wearing environment (slightly dry state), there may be a problem that the contact lens is adsorbed to the eyes. Under such circumstances, the following ophthalmic lens materials have been proposed.

  For example, as an ophthalmic lens material such as a contact lens or an intraocular lens, it is composed of at least 90% by weight of an acrylic acrylic hydrophobic monomer such as phenoxyethyl acrylate and a hydrophilic monomer, and has a stretch ratio of at least 150%, and can be bent flexibly. It has been proposed to use a simple material (for example, Patent Document 1). In addition, a copolymer composed of about 5 to 40% by weight of an aryl acrylate is used for an intraocular lens (for example, Patent Document 2), has a high refractive index, excellent flexibility and shape recovery, and low adhesiveness. Use of a polymer comprising an aromatic ring-containing acrylate and a fluorine atom-containing alkyl acrylate as a soft intraocular lens material (for example, Patent Document 3), an aromatic ring-containing (meth) acrylate such as phenoxyethyl acrylate, hydrophilic The use of a copolymer composed of a monomer or the like as an intraocular lens material (for example, Patent Document 4) is disclosed.

  Also, for the purpose of improving strength and tackiness, fluorine-containing (meth) acrylic acid ester, alkoxy-containing (meth) acrylic acid ester, polysiloxane macromonomer having a polymerizable group at both ends, and urethane bond containing a polymerizable group A soft ophthalmic lens material obtained by copolymerizing a copolymer component composed of a polysiloxane macromonomer is disclosed (for example, Patent Document 5). In addition, a lens material (for example, Patent Documents 6 and 7) including a urethane bond-containing polysiloxane macromonomer having a polymerizable group and a monomer copolymerizable therewith is disclosed.

  However, these lens materials have a problem that even if the adhesiveness is reduced, there is no appropriate balance between strength and flexibility or elasticity, and even if the strength is high, the flexibility is insufficient. was there.

Japanese National Patent Publication No. 10-504059 JP-A-4-292609 JP-A-9-73052 Japanese Patent Laid-Open No. 11-56998 JP 7-157523 A JP-A-4-268314 Japanese Patent Laid-Open No. 5-5861

  In the present invention, it is not only transparent, but also has low adhesiveness, is not adsorbed on the cornea when worn, is safe, has excellent operability (does not stick to fingers), and has moderate strength, flexibility or elasticity. An object of the present invention is to provide an ophthalmic lens material that is excellent in shape stability due to a good balance.

  The present invention relates to a compound (A) having an ethylenically unsaturated group and a group containing a polydimethylsiloxane structure via a urethane bond, the general formula (1):

(Wherein R ¹ is a methyl group or an ethyl group, and n is an integer of 1 to 6), or the general formula (2):

(Wherein R ¹ is a methyl group or an ethyl group, and n is an integer of 1 to 6) and the alkoxy group-containing acrylate (B) and the general formula (3):

Wherein R ² is an aromatic ring in which a hydrogen atom may be substituted with a substituent, X is an oxygen atom or a direct bond, and m is an integer of 1 to 5. Comprising a copolymerization component containing phenylalkyl acrylate or phenoxyalkyl acrylate (C),
The present invention relates to an ophthalmic lens material having a stress in a tensile test at 35 ° C. of 0.1 to 10 MPa, an elongation of 10 to 300%, and a Young's modulus of 0.4 to 3.0 MPa.

  The copolymerization ratio of the compound (A) and the alkoxy group-containing acrylate (B) is preferably 95: 5 to 30:70.

  The content of phenylalkyl acrylate or phenoxyalkyl acrylate (C) in the copolymer component is preferably 3 to 30% by weight.

Compound (A) has the general formula (4):
A ¹ -U ¹ -(-S ¹ -U ^2- ) _p -S ² -U ³ -A ² (4)
[In the formula, A ¹ represents the general formula (4-I):
^{Y 21 -Z 21 -R 31 - (} 4-I)
Wherein Y ²¹ is a (meth) acryloyl group, vinyl group or allyl group, Z ²¹ is an oxygen atom or a direct bond, R ³¹ is a direct bond or a linear, branched or aromatic ring having 1 to 12 carbon atoms. An alkylene group having
A ² represents the general formula (4-II):
-R ³⁴ -Z ²² -Y ²² (4-II)
(Wherein Y ²² is a (meth) acryloyl group, vinyl group or allyl group, Z ²² is an oxygen atom or a direct bond, R ³⁴ is a direct bond, or a linear, branched or aromatic ring having 1 to 12 carbon atoms. A group represented by an alkylene group) (Y ²¹ in the general formula (4-I) and Y ²² in the general formula (4-II) may be the same or different. ) And
U ¹ represents the general formula (4-III):
-X ²¹ -E ²¹ -X ²⁵ -R ^32- (4-III)
(Wherein, X ²¹ and X ²⁵ are each independently a direct bond, selected from oxygen atom and an alkylene glycol group, E ²¹ is -NHCO- group (however, in this case, X ²¹ is a direct bond, X ²⁵ Is an oxygen atom or an alkylene glycol group, E ²¹ forms a urethane bond with X ²⁵ , —CONH— group (where X ²¹ is an oxygen atom or an alkylene glycol group, and X ²⁵ is a direct bond, a divalent group E ²¹ is X ²¹ and forms a urethane bond) or a saturated or unsaturated aliphatic, from diisocyanate selected from the group consisting of alicyclic and aromatic (However, in this case, X ²¹ and X ²⁵ are each independently selected from the oxygen atom and an alkylene glycol group, E ²¹ forms two urethane bonds between X ²¹ and X ²⁵⁾ R ³² is a group represented by an alkylene group having a linear or branched chain having 1 to 6 carbon atoms),
S ¹ and S ² are each independently general formula (4-IV):

Wherein R ²³ , R ²⁴ , R ²⁵ , R ²⁶ , R ²⁷ and R ²⁸ are each independently an alkyl group having 1 to 6 carbon atoms, a fluorine-substituted alkyl group or a phenyl group, and K is 10 to 100 L is an integer of 0 or 1 to 90, and K + L is an integer of 10 to 100),
U ² represents the general formula (4-V):
^{-R 37 -X 27 -E 24 -X 28} -R 38 - (4-V)
(Wherein the alkylene group having a linear or branched R ³⁷ and R ³⁸ having 1 to 6 carbon atoms independently; each X ²⁷ and X ²⁸ is independently oxygen atom or an alkylene glycol group; E ²⁴ Is a divalent group derived from a diisocyanate selected from the group consisting of saturated or unsaturated aliphatic, alicyclic and aromatic groups (wherein E ²⁴ is two between X ²⁷ and X ²⁸ Which forms a urethane bond).
U ³ represents the general formula (4-VI):
^{-R 33 -X 26 -E 22 -X 22} - (4-VI)
(Wherein, R ³³ is selected from linear or branched chain alkylene group having, X ²² and X ²⁶ are each independently a direct bond, an oxygen atom and an alkylene glycol group having 1 to 6 carbon atoms, E ²² is —NHCO— group (wherein X ²² is an oxygen atom or an alkylene glycol group, X ²⁶ is a direct bond, E ²² forms a urethane bond with X ²² ), —CONH— group ( However, in this case, X ²² is a direct bond, X ²⁶ is an oxygen atom or an alkylene glycol group, and E ²² forms a urethane bond with X ²⁶ ), or a saturated or unsaturated aliphatic system, ring system and a divalent radical of a diisocyanate from selected from the group consisting of aromatic (However, in this case, X ²² and X ²⁶ are each independently selected from oxygen atom and an alkylene glycol group E ²² is a group represented by form two urethane bonds are) between X ²² and X ^26,
p represents 0 or an integer of 1 to 10. Or a polysiloxane macromonomer represented by the general formula (5):
A ¹ −U ¹ −T ¹ −U ⁴ − (− S ¹ −U ² −) _p −S ² −U ⁵ −T ² −U ³ −A ² (5)
[Wherein, A ¹ , A ² , U ¹ , U ² , U ³ , S ¹ , S ² , and p are the same as those in the general formula (4), and U ⁴ and U ⁵ represent U ¹ , U ³ and is the same. However, Y ²¹ and Y ²² in A ¹ and A ² are a (meth) acryloyl group, a vinyl group or an allyl group.
T ¹ and T ² are represented by the general formula (5-I):
_{-Q- (CH 2 CHD-Q-)} q - (5-I)
(In the formula, D is a hydrogen atom, a methyl group or a hydroxyl group, Q is a direct bond or an oxygen atom, and q is an integer of 5 to 10,000), or General Formula (5-II):
-(M) _r- (5-II)
(In the formula, M is 1-methyl-3-methylene-2-pyrrolidone, N-vinyl-2-pyrrolidone, (meth) acrylic acid, (meth) acrylate, N, N-dimethyl (meth) acrylamide, Indicates a hydrophilic monomer unit selected from N, N-diethyl (meth) acrylamide, 2-hydroxyethyl (meth) acrylate, tetrahydrofuran, oxetane, oxazoline and 2-methacryloyloxyethyl phosphorylcholine, and is composed of hydrophilic monomer units The polymerization chain of the polymer may be linear or branched, and may be bonded in a random or block form, where r is an integer of 5 to 10,000) or a hydrophilic polymer-containing segment or hydrophilic It is a functional oligomer-containing segment. It is preferable that it is a polysiloxane macromonomer represented by this.

  The alkoxy group-containing acrylate (B) is preferably (B1) methoxyethyl acrylate, (B2) ethoxyethyl acrylate, or (B3) methoxytriethylene glycol acrylate (B3).

  The phenylalkyl acrylate or phenoxyalkyl acrylate (C) is preferably phenoxyethyl acrylate.

  The ophthalmic lens material of the present invention is not only sticky but also has no stickiness, is not adsorbed on the cornea when worn, is safe and easy to operate (does not stick to fingers), and further has strength and flexibility. Alternatively, an appropriate balance of elasticity provides an effect of having shape stability because it is moderately flexible while maintaining strength.

  The ophthalmic lens material of the present invention comprises a compound (A) having an ethylenically unsaturated group and a group containing a polydimethylsiloxane structure via a urethane bond, and a general formula (1):

(Wherein R ¹ is a methyl group or an ethyl group, and n is an integer of 1 to 6), or the general formula (2):

(Wherein R ¹ is a methyl group or an ethyl group, and n is an integer of 1 to 6) and the alkoxy group-containing acrylate (B) and the general formula (3):

Wherein R ² is an aromatic ring in which a hydrogen atom may be substituted with a substituent, X is an oxygen atom or a direct bond, and m is an integer of 1 to 5. It is obtained by copolymerizing a copolymer component comprising a copolymer component containing phenylalkyl acrylate or phenoxyalkyl acrylate (C).

The compound (A) has a role of imparting oxygen permeability and flexibility. As the compound (A), for example, the general formula (4):
A ¹ -U ¹ -(-S ¹ -U ^2- ) _p -S ² -U ³ -A ² (4)
[In the formula, A ¹ represents the general formula (4-I):
^{Y 21 -Z 21 -R 31 - (} 4-I)
Wherein Y ²¹ is a (meth) acryloyl group, vinyl group or allyl group, Z ²¹ is an oxygen atom or a direct bond, R ³¹ is a direct bond or a linear, branched or aromatic ring having 1 to 12 carbon atoms. An alkylene group having
A ² represents the general formula (4-II):
-R ³⁴ -Z ²² -Y ²² (4-II)
(Wherein Y ²² is a (meth) acryloyl group, vinyl group or allyl group, Z ²² is an oxygen atom or a direct bond, R ³⁴ is a direct bond, or a linear, branched or aromatic ring having 1 to 12 carbon atoms. A group represented by an alkylene group) (Y ²¹ in the general formula (4-I) and Y ²² in the general formula (4-II) may be the same or different. ) And
U ¹ represents the general formula (4-III):
-X ²¹ -E ²¹ -X ²⁵ -R ^32- (4-III)
(Wherein, X ²¹ and X ²⁵ are each independently a direct bond, selected from oxygen atom and an alkylene glycol group, E ²¹ is -NHCO- group (however, in this case, X ²¹ is a direct bond, X ²⁵ Is an oxygen atom or an alkylene glycol group, E ²¹ forms a urethane bond with X ²⁵ , —CONH— group (where X ²¹ is an oxygen atom or an alkylene glycol group, and X ²⁵ is a direct bond, a divalent group E ²¹ is X ²¹ and forms a urethane bond) or a saturated or unsaturated aliphatic, from diisocyanate selected from the group consisting of alicyclic and aromatic (However, in this case, X ²¹ and X ²⁵ are each independently selected from the oxygen atom and an alkylene glycol group, E ²¹ forms two urethane bonds between X ²¹ and X ²⁵⁾ R ³² is a group represented by an alkylene group having a linear or branched chain having 1 to 6 carbon atoms),
S ¹ and S ² are each independently general formula (4-IV):

Wherein R ²³ , R ²⁴ , R ²⁵ , R ²⁶ , R ²⁷ and R ²⁸ are each independently an alkyl group having 1 to 6 carbon atoms, a fluorine-substituted alkyl group or a phenyl group, and K is 10 to 100 L is an integer of 0 or 1 to 90, and K + L is an integer of 10 to 100),
U ² represents the general formula (4-V):
^{-R 37 -X 27 -E 24 -X 28} -R 38 - (4-V)
(Wherein the alkylene group having a linear or branched R ³⁷ and R ³⁸ having 1 to 6 carbon atoms independently; each X ²⁷ and X ²⁸ is independently oxygen atom or an alkylene glycol group; E ²⁴ Is a divalent group derived from a diisocyanate selected from the group consisting of saturated or unsaturated aliphatic, alicyclic and aromatic groups (wherein E ²⁴ is two between X ²⁷ and X ²⁸ Which forms a urethane bond).
U ³ represents the general formula (4-VI):
^{-R 33 -X 26 -E 22 -X 22} - (4-VI)
(Wherein, R ³³ is selected from linear or branched chain alkylene group having, X ²² and X ²⁶ are each independently a direct bond, an oxygen atom and an alkylene glycol group having 1 to 6 carbon atoms, E ²² is —NHCO— group (wherein X ²² is an oxygen atom or an alkylene glycol group, X ²⁶ is a direct bond, E ²² forms a urethane bond with X ²² ), —CONH— group ( However, in this case, X ²² is a direct bond, X ²⁶ is an oxygen atom or an alkylene glycol group, and E ²² forms a urethane bond with X ²⁶ ), or a saturated or unsaturated aliphatic system, ring system and a divalent radical of a diisocyanate from selected from the group consisting of aromatic (However, in this case, X ²² and X ²⁶ are each independently selected from oxygen atom and an alkylene glycol group E ²² is a group represented by form two urethane bonds are) between X ²² and X ^26,
p represents 0 or an integer of 1 to 10. The polysiloxane macromonomer represented by formula (I) is preferable, and is preferable in terms of improving the flexibility of the obtained ophthalmic lens material and improving oxygen permeability.

In the general formula (4), A ¹ represents the general formula (4-I):
^{Y 21 -Z 21 -R 31 - (} 4-I)
Wherein Y ²¹ , Z ²¹ and R ³¹ are the same as defined above, and A ² represents the general formula (4-II):
-R ³⁴ -Z ²² -Y ²² (4-II)
(Wherein Y ²² , Z ²² and R ³⁴ are the same as described above).

Each of Y ²¹ and Y ²² is a polymerizable group, but an acryloyl group is particularly preferred from the viewpoints of high polymerization reactivity, polymerization in a short time, and excellent copolymerizability with other components.

Z ²¹ and Z ²² are both an oxygen atom or a direct bond, preferably an oxygen atom.

Each of R ³¹ and R ³⁴ is an alkylene group having a direct bond or a linear, branched or aromatic ring having 1 to 12 carbon atoms, preferably an ethylene group, a propylene group or a butylene group.

U ¹ , U ² and U ³ all represent a group containing a urethane bond in the molecular chain of the compound (A).

In U ¹ and U ³ , E ²¹ and E ²² are each selected from the group of —CONH— group, —NHCO— group or saturated or unsaturated aliphatic system, alicyclic system and aromatic system as described above. Represents a divalent group derived from diisocyanate. Here, examples of the divalent group derived from diisocyanate selected from the group consisting of saturated or unsaturated aliphatic, alicyclic and aromatic groups include ethylene diisocyanate, 1,3-diisocyanate propane, hexamethylene diisocyanate and the like. A divalent group derived from a saturated aliphatic diisocyanate; a divalent group derived from an alicyclic diisocyanate such as 1,2-diisocyanatecyclohexane, bis (4-isocyanatocyclohexyl) methane, isophorone diisocyanate; Divalent groups derived from aromatic diisocyanates such as 1,5-diisocyanate naphthalene; divalent groups derived from unsaturated aliphatic diisocyanates such as 2,2′-diisocyanate diethyl fumarate. Among these, a divalent group derived from hexamethylene diisocyanate, a divalent group derived from tolylene diisocyanate, and a divalent group derived from isophorone diisocyanate are preferable because they are relatively easily available and easily imparted strength.

In U ¹ , when E ²¹ is a —NHCO— group, X ²¹ is a direct bond, X ²⁵ is an oxygen atom or an alkylene glycol group, and E ²¹ is represented by X ²⁵ and the formula: —NHCOO—. Form a urethane bond. When E ²¹ is a —CONH— group, X ²¹ is an oxygen atom or an alkylene glycol group, X ²⁵ is a direct bond, and E ²¹ is a urethane represented by X ²¹ and the formula: —OCONH—. Form a bond. Further, when E ²¹ is a divalent group derived from the diisocyanate, X ²¹ and X ²⁵ are each independently selected from an oxygen atom and preferably an alkylene glycol group having 1 to 6 carbon atoms, and E ²¹ is X so as to form two urethane bonds in between the ²¹ and X ^25. R ³² is an alkylene group having a linear or branched chain having 1 to 6 carbon atoms.

In U ² , E ²⁴ represents a divalent group derived from a diisocyanate selected from the group consisting of saturated or unsaturated aliphatic, alicyclic and aromatic groups, as described above. Here, as the divalent group derived from diisocyanate selected from the group of saturated or unsaturated aliphatic, alicyclic and aromatic groups, for example, the same divalent group as in U ¹ and U ³ described above is used. Group. Among these, a divalent group derived from hexamethylene diisocyanate, a divalent group derived from tolylene diisocyanate, and a divalent group derived from isophorone diisocyanate are preferable because they are relatively easily available and easily imparted strength. E ²⁴ forms two urethane bonds between X ²⁷ and X ²⁸ . X ²⁷ and X ²⁸ are each independently an oxygen atom or preferably an alkylene glycol group having 1 to 6 carbon atoms, and R ³⁷ and R ³⁸ are each independently a linear or branched chain having 1 to 6 carbon atoms. Is an alkylene group.

In U ^3, R ³³ is an alkylene group having a linear or branched chain having 1 to 6 carbon atoms. When E ²² is a —NHCO— group, X ²² is an oxygen atom or an alkylene glycol group, X ²⁶ is a direct bond, E ²² is a urethane bond represented by X ²² and the formula: —NHCOO—. Form. When E ²² is a —CONH— group, X ²² is a direct bond, X ²⁶ is an oxygen atom or an alkylene glycol group, and E ²² is a urethane represented by X ²⁶ and the formula: —OCONH—. Form a bond. Further, when E ²² is a divalent group derived from the diisocyanate, X ²² and X ²⁶ are each independently selected from an oxygen atom and preferably an alkylene glycol group having 1 to 6 carbon atoms, and E ²² is X so as to form two urethane bonds in between the ²² and X ^26.

Here, the alkylene glycol preferably having 1 to 20 carbon atoms in X ²¹ , X ²⁵ , X ²⁷ , X ²⁸ , X ²² and X ²⁶ is, for example, the general formula (4-VII):
_{-O- (C x H 2x -O)} y - (4-VII)
(Wherein x represents an integer of 1 to 4 and y represents an integer of 1 to 5).

S ¹ and S ² are both groups represented by the general formula (4-IV) as described above.

In the general formula (4-IV), R ²³ , R ²⁴ , R ²⁵ , R ²⁶ , R ²⁷ and R ²⁸ are each independently an alkyl group having 1 to 6 carbon atoms and fluorine-substituted, as described above. An alkyl group or a phenyl group;

  Examples of the fluorine-substituted alkyl group include 3,3,3-trifluoro-n-propyl group, 3,3,3-trifluoroisopropyl group, 3,3,3-trifluoro-n-butyl group, 3,3,3-trifluoroisobutyl group, 3,3,3-trifluoro-sec-butyl group, 3,3,3-trifluoro-t-butyl group, 3,3,3-trifluoro-n- Examples thereof include a pentyl group, a 3,3,3-trifluoroisopentyl group, a 3,3,3-trifluorothiopentyl group, and a 3,3,3-trifluorohexyl group. In the present invention, when the compound (A) having such a fluorine-substituted alkyl group is used and its blending amount is increased, the anti-lipid contamination property of the obtained ophthalmic lens material tends to be improved.

  K is an integer of 10 to 100, L is 0 or an integer of 1 to 90, and K + L is preferably an integer of 10 to 100, more preferably 10 to 80. When K + L is larger than 100, the molecular weight of the compound (A) becomes large, the compatibility between this and other components deteriorates, and it does not dissolve uniformly at the time of blending, or phase separation occurs at the time of polymerization, resulting in white turbidity. Present, there is a tendency that a uniform and transparent ophthalmic lens material cannot be obtained, and when it is less than 10, the oxygen permeability of the obtained ophthalmic lens material tends to be low and the flexibility tends to be lowered.

  Further, p is preferably 0 or an integer of 1 to 10. When p is larger than 10, the molecular weight of the compound (A) is increased, the compatibility with other components is deteriorated, it does not dissolve uniformly at the time of blending, or phase separation occurs at the time of polymerization, resulting in white turbidity. Therefore, there is a tendency that a transparent ophthalmic lens material cannot be obtained. p is more preferably 0 or an integer of 1 to 5.

Moreover, as a compound (A), general formula (5):
A ¹ −U ¹ −T ¹ −U ⁴ − (− S ¹ −U ² −) _p −S ² −U ⁵ −T ² −U ³ −A ² (5)
[Wherein, A ¹ , A ² , U ¹ , U ² , U ³ , S ¹ , S ² , and p are the same as those in the general formula (4), and U ⁴ and U ⁵ represent U ¹ , U ³ and is the same. However, Y ²¹ and Y ²² in A ¹ and A ² are a (meth) acryloyl group, a vinyl group or an allyl group.
T ¹ and T ² are represented by the general formula (5-I):
_{-Q- (CH 2 CHD-Q-)} q - (5-I)
(In the formula, D is a hydrogen atom, a methyl group or a hydroxyl group, Q is a direct bond or an oxygen atom, and q is an integer of 5 to 10,000), or General Formula (5-II):
-(M) _r- (5-II)
(In the formula, M is 1-methyl-3-methylene-2-pyrrolidone, N-vinyl-2-pyrrolidone, (meth) acrylic acid, (meth) acrylate, N, N-dimethyl (meth) acrylamide, Indicates a hydrophilic monomer unit selected from N, N-diethyl (meth) acrylamide, 2-hydroxyethyl (meth) acrylate, tetrahydrofuran, oxetane, oxazoline and 2-methacryloyloxyethyl phosphorylcholine, and is composed of hydrophilic monomer units The polymerization chain of the polymer may be linear or branched, and may be bonded in a random or block form, where r is an integer of 5 to 10,000) or a hydrophilic polymer-containing segment or hydrophilic It is a functional oligomer-containing segment. ], Which is preferable in terms of improving compatibility with other components and making it difficult to become clouded.

  The compound (A) preferably has a hydrophilic polymer structure. With this structure, the compatibility between the compound (A) and the hydrophilic monomer is improved, and the water wettability of the material made of these can be improved. As the structure of the hydrophilic polymer portion, polyethylene glycol, polypropylene glycol, polyvinyl alcohol, polyvinyl pyrrolidone, poly (meth) acrylic acid, poly (meth) acrylate, poly (2-hydroxyethyl (meth) acrylate), polytetrahydrofuran And one or more polymers obtained by polymerizing zwitterionic group-containing monomers such as polyoxetane, polyoxazoline, polydimethylacrylamide, polydiethylacrylamide, and poly (2-methacryloyloxyethylphosphorylcholine). The molecular weight of the hydrophilic polymer structure portion is 100 to 1,000,000, preferably 1,000 to 500,000. When the molecular weight is less than 100, there is a tendency that hydrophilicity sufficient to dissolve the compound (A) in the hydrophilic monomer cannot be imparted. On the other hand, when the molecular weight exceeds 1,000,000, hydrophilic / hydrophobic domains tend to be large and a transparent material tends not to be obtained.

  Representative examples of compound (A) include, for example, the formula:

A compound represented by formula (hereinafter referred to as compound (A-1)), formula:

(Wherein, q is an integer of 5 to 10,000), and the like (hereinafter referred to as compound (A-2)). These can be used alone or in admixture of two or more.

  The content of the compound (A) is preferably 20 to 95% by weight, more preferably 30 to 70% by weight in all copolymer components. If the content of the compound (A) is less than 20% by weight, sufficient flexibility and oxygen permeability tend not to be obtained, and if it exceeds 95% by weight, the tackiness increases and the strength tends to be weak. There is.

  The alkoxy group-containing acrylate (B) has the general formula (1):

Or general formula (2):

It has a role which reduces adhesiveness.

In the general formula (1) and the formula (2), R ¹ is a methyl or ethyl group, n represents an integer from 1 to 6, preferably an integer of 1 to 4. When n exceeds 6, the hydrophilicity becomes strong and the compatibility with the hydrophobic compound (A) is deteriorated, and it does not dissolve uniformly at the time of blending, or phase separation occurs at the time of polymerization and it becomes white turbid and uniform and transparent. Can not be obtained.

  Specific examples of the alkoxy group-containing acrylate (B) include, for example, methoxyethyl acrylate (B1), ethoxyethyl acrylate (B2), methoxypropyl acrylate, methoxydiethylene glycol acrylate, ethoxydiethylene glycol acrylate, methoxytriethylene glycol acrylate (B3), and the like. Is given. Among these, methoxyethyl acrylate (B1), ethoxyethyl acrylate (B2), and methoxytriethylene glycol acrylate (B3) are preferable, and methoxyethyl acrylate (B1) is particularly preferable in terms of reducing surface tackiness.

  The copolymerization ratio of the compound (A) and the alkoxy group-containing acrylate (B) is preferably a weight ratio of 95: 5 to 30:70, more preferably 70:30 to 40:60. As a result, the material becomes transparent without being clouded, and an appropriate balance of strength and flexibility can be brought about. If the amount of the alkoxy group-containing acrylate (B) is too small relative to the compound (A), there is a tendency that the tackiness cannot be sufficiently reduced. If the amount is too large, the strength of the resulting material is lowered and the ophthalmic lens is easily damaged. , Oxygen permeability tends to be low.

  The content of the alkoxy group-containing acrylate (B) in all copolymer components is preferably 2 to 70% by weight, more preferably 10 to 60% by weight. If the content of the alkoxy group-containing acrylate (B) is less than 2% by weight, the tackiness of the ophthalmic lens tends not to be sufficiently reduced, and if it exceeds 70% by weight, the strength of the obtained material is lowered, and the ophthalmic lens is reduced. There is a tendency to break easily.

  The phenylalkyl acrylate or phenoxyalkyl acrylate (C) is a component for further reinforcing the strength of the ophthalmic lens. The general formula (3):

It is represented by

In the general formula (3), R ² is an aromatic ring in which a hydrogen atom may be substituted with a substituent, and X is an oxygen atom or a direct bond. m is an integer of 1 to 5, preferably an integer of 1 to 3. When m is more than 5, the hydrophobicity becomes strong and the compatibility with the hydrophilic alkoxy group-containing acrylate (B) is deteriorated, so that it does not dissolve uniformly at the time of blending, or phase separation occurs at the time of polymerization and white turbidity is exhibited. A uniform and transparent ophthalmic lens material cannot be obtained.

  Specific examples of phenylalkyl acrylate or phenoxyalkyl acrylate (C) include phenylethyl acrylate and phenoxyethyl acrylate. Of these, 2-phenoxyethyl acrylate is preferable because it is more excellent in strength.

  The content of phenylalkyl acrylate or phenoxyalkyl acrylate (C) in all copolymer components is preferably 3 to 30% by weight, more preferably 5 to 20% by weight. If the proportion of phenylalkyl acrylate or phenoxyalkyl acrylate (C) is less than 3% by weight, the effect of reinforcing the strength of the obtained material tends to be difficult to obtain, and if it exceeds 30% by weight, the flexibility tends to decrease.

  In the present invention, since an acrylate instead of a methacrylate is used for the alkoxy group-containing acrylate (B) and the phenylalkyl acrylate or phenoxyalkyl acrylate (C), the polymerization is highly reactive and the polymerization can be obtained in a short time. It has the advantage that the flexibility of the material is improved.

  Furthermore, when each component of the compound (A), alkoxy group-containing acrylate (B), phenylalkyl acrylate or phenoxyalkyl acrylate (C) is difficult to mix, an amphiphile as another copolymerization component for the purpose of imparting compatibility. Sexual components can be added. Examples of the amphiphilic component include 2-ethylhexyl acrylate and dimethylacrylamide.

  The content of the amphiphilic component in the total copolymer component is preferably 5 to 50% by weight, more preferably 10 to 35% by weight. If the content of the amphiphilic component is less than 5% by weight, there is a tendency that compatibility cannot be imparted. If the content exceeds 50% by weight, the compound (A) which is an essential copolymerization component, the alkoxy group-containing acrylate (B) and There is a tendency that the content of phenylalkyl acrylate or phenoxyalkyl acrylate (C) is relatively small, and the effect of such copolymerization components is not sufficiently exhibited.

  Moreover, a crosslinking agent can be used in order to further improve durability such as shape stability and chemical resistance, heat resistance, solvent resistance, and shape stability of the ophthalmic lens material and to reduce the amount of eluate. In this case, a macromonomer having at least two polymerizable groups in the molecule may be used as a crosslinking agent.

  Specific examples of the crosslinking agent include ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, and 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 (meth) acrylate, 3-vinylbenzyl (meth) acrylate, 2,2-bis (p- (meth) acryloyloxyphenyl) hexafluoro Lopropane, 2,2-bis (m- (meth) acryloyloxyphenyl) hexafluoropropane, 2,2-bis (o- (meth) acryloyloxyphenyl) hexafluoropropane, 2,2-bis (p- (meta ) Acryloyloxyphenyl) 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) be Zen, 1,3-bis (2- (meth) acryloyloxy isopropyl) benzene, 1,2-bis (2- (meth) acryloyloxy isopropyl) benzene. These crosslinking agents are used alone or in admixture of two or more.

  The amount of the crosslinking agent is preferably 0.01 to 10% by weight, more preferably 0.1 to 5% by weight, and particularly preferably 0.01 to 10% by weight, based on all copolymer components. When the blending amount of the crosslinking agent is less than 0.01% by weight, the effect of blending the crosslinking agent is not sufficiently exhibited, and when it exceeds 10% by weight, the material tends to become brittle.

  Furthermore, a reinforcing monomer can be blended for the purpose of appropriately adjusting the strength of the obtained material. Specific examples of the reinforcing monomer include (meth) acrylic acid; styrenes such as styrene, methylstyrene and dimethylaminostyrene; aromatic ring-containing (meth) acrylates such as benzyl (meth) acrylate; and alkyl groups. And unsaturated organic acid esters such as itaconic acid, crotonic acid, maleic acid and fumaric acid. These reinforcing monomers are used alone or in admixture of two or more.

  Moreover, a hydrophilic monomer can be blended for the purpose of imparting hydrophilicity. Specific examples of the hydrophilic monomer include hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, hydroxybutyl (meth) acrylate, dihydroxypropyl (meth) acrylate, dihydroxybutyl (meth) acrylate, and diethylene glycol mono (meth). Hydroxyl group-containing (meth) acrylate such as acrylate, triethylene glycol mono (meth) acrylate, dipropylene glycol mono (meth) acrylate; (meth) acrylic acid; N-vinylpyrrolidone, α-methylene-N-methylpyrrolidone, N- Vinyl lactams such as vinyl caprolactam and N- (meth) acryloylpyrrolidone; (meth) acrylamide, N-methyl (meth) acrylamide, N-ethyl (meth) acrylamide (Meth) acrylamide such as N-hydroxyethyl (meth) acrylamide, N, N-dimethyl (meth) acrylamide, N, N-diethyl (meth) acrylamide, N-ethylaminoethyl (meth) acrylamide; aminoethyl (meth) Examples thereof include aminoalkyl (meth) acrylates such as acrylate, N-methylaminoethyl (meth) acrylate, and N, N-dimethylaminoethyl (meth) acrylate. These hydrophilic monomers are used alone or in admixture of two or more.

  Moreover, you may mix | blend the monomer which provides favorable oxygen permeability for the purpose of improving oxygen permeability supplementarily. Specific examples of such monomers include pentamethyldisiloxanylmethyl (meth) acrylate, pentamethyldisiloxanylpropyl (meth) acrylate, methylbis (trimethylsiloxy) silylpropyl (meth) acrylate, and tris (trimethylsiloxy). Silylpropyl (meth) acrylate, mono [methylbis (trimethylsiloxy) siloxy] bis (trimethylsiloxy) silylpropyl (meth) acrylate, tris [methylbis (trimethylsiloxy) siloxy] silylpropyl (meth) acrylate, methylbis (trimethylsiloxy) silyl Propyl glyceryl (meth) acrylate, tris (trimethylsiloxy) silylpropyl glyceryl (meth) acrylate, mono [methylbis (trimethylsiloxy) Siloxy] bis (trimethylsiloxy) silylpropyl glyceryl (meth) acrylate, trimethylsilylethyltetramethyldisiloxanylpropyl glyceryl (meth) acrylate, trimethylsilylmethyl (meth) acrylate, trimethylsilylpropyl (meth) acrylate, trimethylsilylpropyl glyceryl (meth) Acrylate, pentamethyldisiloxanylpropylglyceryl (meth) acrylate, methylbis (trimethylsiloxy) silylethyltetramethyldisiloxanylmethyl (meth) acrylate, tetramethyltriisopropylcyclotetrasiloxanylpropyl (meth) acrylate, tetra Methyltriisopropylcyclotetrasiloxybis (trimethylsiloxy) silylpropyl (meth) acryl Silicon-containing (meth) acrylates such as benzoate; pentafluorostyrene, trimethylstyrene, trifluoromethylstyrene, (pentamethyl-3,3-bis (trimethylsiloxy) trisiloxanyl) styrene, (hexamethyl-3-trimethylsiloxytrisiloxa) Nyl) Fluorine such as styrene or silicon-containing styrenes; Fluorine-containing alkyl groups such as itaconic acid, crotonic acid, maleic acid, fumaric acid and / or alkyl esters optionally substituted with siloxanyl alkyl groups It is done. These monomers are used alone or in admixture of two or more.

  The amount of the reinforcing monomer, hydrophilic monomer, and monomer that imparts oxygen permeability is preferably adjusted as appropriate according to the intended use of the material to be obtained. In particular, it is preferably 20% by weight or less. When the content of these monomers is more than 30% by weight, the content of the essential copolymerization component (A), alkoxy group-containing acrylate (B) and phenylalkyl acrylate or phenoxyalkyl acrylate (C) is relatively There is a tendency that the effect of the copolymer component is not sufficiently exhibited.

  When the hydrophilic monomer is blended, the blended amount of the hydrophilic monomer is 15% by weight or less in the total copolymerization component, so that the obtained ophthalmic lens material is substantially non-hydrous or low in water content. It is preferable when it is made water-containing. For example, when the ophthalmic lens material of the present invention is used for a contact lens, it is preferable that the ophthalmic lens material is substantially non-hydrated or very low in water content. If the ophthalmic lens material is substantially free of water, microorganisms such as bacteria will not enter or propagate in the lens, so there is no need to regularly perform complicated lens care such as disinfection. In addition, a decrease in mechanical strength due to an increase in moisture content is reduced. Further, when used as an intraocular lens, if it is substantially non-hydrated, the decrease in strength due to the increase in moisture content is small, and the shape retention as a lens is not impaired.

  The copolymerization component may be a polymerizable ultraviolet absorber for the purpose of imparting ultraviolet absorptivity to the lens, coloring the lens, or cutting light in a part of the wavelength range of visible light. A polymerizable dye or a polymerizable ultraviolet-absorbing dye can be blended.

  Specific examples of the polymerizable ultraviolet absorber include, for example, 2-hydroxy-4- (meth) acryloyloxybenzophenone, 2-hydroxy-4- (meth) acryloyloxy-5-tert-butylbenzophenone, 2-hydroxy- Benzophenone-based polymerizable ultraviolet absorbers such as 4- (meth) acryloyloxy-2 ′, 4′-dichlorobenzophenone and 2-hydroxy-4- (2′-hydroxy-3 ′-(meth) acryloyloxypropoxy) benzophenone; 2- (2'-hydroxy-5 '-(meth) acryloyloxyethylphenyl) -2H-benzotriazole, 2- (2'-hydroxy-5'-(meth) acryloyloxyethylphenyl) -5-chloro-2H -Benzotriazole, 2- (2'-hydroxy-5 '-(meth) a Benzo such as liloyloxypropylphenyl) -2H-benzotriazole, 2- (2'-hydroxy-5 '-(meth) acryloyloxypropyl-3'-tert-butylphenyl) -5-chloro-2H-benzotriazole Triazole-based polymerizable UV absorbers; salicylic acid derivative-based polymerizable UV absorbers such as phenyl 2-hydroxy-4-methacryloyloxymethylbenzoate; 2-cyano-3-phenyl-3- (3 ′-(meth) acryloyloxy Examples thereof include polymerizable ultraviolet absorbers such as phenyl) propenyl acid methyl ester. These polymerizable ultraviolet absorbers are used alone or in admixture of two or more.

  Specific examples of the polymerizable dye include 1-phenylazo-4- (meth) acryloyloxynaphthalene, 1-phenylazo-2-hydroxy-3- (meth) acryloyloxynaphthalene, 1-naphthylazo-2-hydroxy- Azo polymerizable dyes such as 3- (meth) acryloyloxynaphthalene; 1,5-bis ((meth) acryloylamino) -9,10-anthraquinone, 1- (4′-vinylbenzoylamide) -9,10- Anthraquinone polymerizable dyes such as anthraquinone; nitro polymerizable dyes such as o-nitroanilinomethyl (meth) acrylate; (meth) acryloylated tetraamino copper phthalocyanine, (meth) acryloylated (dodecanoylated tetraamino copper phthalocyanine) Phthalocyanine polymerizable dyes such as And the like. These polymerizable dyes are used alone or in admixture of two or more.

  Specific examples of the polymerizable ultraviolet absorbing dye include 2,4-dihydroxy-3- (p-styrenoazo) benzophenone, 2,4-dihydroxy-5- (p-styrenoazo) benzophenone, and 2,4-dihydroxy. Benzophenone-based polymerizable UV-absorbing dyes such as -3- (p- (meth) acryloyloxymethylphenylazo) benzophenone and benzoic acid-based polymerizable UV rays such as 2-hydroxy-4- (p-styrenoazo) benzoate phenyl Examples include absorptive dyes. These polymerizable ultraviolet absorbing dyes are used alone or in admixture of two or more.

  The blending amount of the polymerizable ultraviolet absorbent, the polymerizable dye and the polymerizable ultraviolet absorbent dye varies depending on the thickness of the lens and cannot be determined unconditionally. However, 3% by weight or less in the total copolymerization component, In particular, it is preferably 0.1 to 2% by weight. If the blending amount is more than 3% by weight, the physical properties of the lens, such as strength, tend to be reduced, and in consideration of the toxicity of the UV absorber and the dye, the contact lens that directly contacts the living tissue or in vivo There is a tendency that it is not suitable as an ophthalmic lens material such as an intraocular lens to be embedded in a lens. In particular, in the case of pigments, if the amount is too large, the color of the lens becomes too dark and the transparency tends to decrease and the lens tends to be difficult to transmit visible light.

  In the present invention, a reinforcing monomer, a hydrophilic monomer, a monomer imparting oxygen permeability, a polymerizable ultraviolet absorber, a polymerizable dye or a polymerizable ultraviolet absorbing dye is selected from one or more. It may be used as a macromonomer.

  Examples of the method for producing the ophthalmic lens material of the present invention include a compound (A), an alkoxy group-containing acrylate (B), a phenyl acrylate or a phenoxyalkyl acrylate (C), and an amphiphilic component that is optionally added, Examples include a method in which other components are blended, a radical polymerization initiator is added thereto, and polymerization is performed by a normal method.

  The normal method is, for example, a method in which a radical polymerization initiator is blended and then gradually heated in a temperature range of room temperature to about 130 ° C., or a method of irradiating electromagnetic waves such as microwaves, ultraviolet rays, and radiation (γ rays). is there. In the case of heat polymerization, the temperature may be raised stepwise. The polymerization may be performed by a bulk polymerization method, a solvent polymerization method using a solvent or the like, or may be performed by other methods.

  Specific examples of the radical polymerization initiator include, for example, azobisisobutyronitrile, azobisdimethylvaleronitrile, benzoyl peroxide, tert-butyl hydroperoxide, cumene hydroperoxide, and the like. An agent is used individually or in combination of 2 or more types. In addition, when making it superpose | polymerize using a light etc., it is preferable to further add photoinitiators and sensitizers, such as 2-hydroxy-2-methyl-2-phenylpropan-1-one. The blending amount of the polymerization initiator and the sensitizer is appropriately about 0.001 to 2 parts by weight, preferably 0.01 to 1 part by weight with respect to 100 parts by weight of all copolymer components.

  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 commonly used by those skilled in the art is employed. Examples of such a molding method include a cutting method and a mold method. In the cutting method, polymerization is performed in an appropriate mold or container to obtain a rod-shaped, block-shaped, or plate-shaped material (polymer), and then processed into a desired shape by mechanical processing such as cutting or polishing. It is a method to do. In the mold method, a mold corresponding to the shape of the desired ophthalmic lens is prepared, and a copolymerized component is polymerized in this mold to obtain a molded product, which is mechanically finished as necessary. Is the method.

  Since the ophthalmic lens material of the present invention is a soft material at a temperature near room temperature, a molding method by a mold method is generally suitable for molding an ophthalmic lens. Known casting methods include spin casting and static casting.

  Further, when an intraocular lens is obtained, the lens support may be manufactured separately from the lens and attached to the lens later, or may be molded simultaneously (integrally) with the lens.

  Further, for example, a soft material described in Japanese Patent Publication No. 5-11541 is impregnated with a monomer that becomes a hard polymer, polymerized, and hardened, and then machined into a desired shape, and the hard polymer is used as a solvent. The method of removing the product and obtaining a soft molded article can be suitably used when producing the ophthalmic lens material of the present invention.

  In the present invention, various surface treatments and the like may be performed after the ophthalmic lens material is molded into a desired ophthalmic lens shape.

  The ophthalmic lens material of the present invention has specific stress, elongation and Young's modulus in a tensile test at 35 ° C.

  That is, the stress at 35 ° C. of the ophthalmic lens material of the present invention is 0.1 to 10 MPa. Since the stress is high, the strength of the ophthalmic lens can be maintained. If it is less than 0.1 MPa, it tends to break, and if it exceeds 10 MPa, it becomes hard and loses its flexibility. The stress is preferably 0.2 to 5.0 MPa, particularly 0.3 to 2.0 MPa.

  The elongation at 35 ° C. is 10 to 300%. Since the elongation rate is large, it is difficult to shake and break, and the strength can be maintained. If the elongation is less than 10%, it is easy to break, and if it exceeds 300%, it is too soft and the shape stability is poor. The elongation percentage is further preferably 20 to 250%, particularly preferably 30 to 200%.

  The Young's modulus at 35 ° C is 0.4 to 3.0 MPa. As described above, when the Young's modulus is within a specific range, moderate flexibility and elasticity can be obtained, and the shape is stable and is moderately flexible. If the Young's modulus is less than 0.4 MPa, it is too soft and the shape stability is poor, and if it exceeds 3.0 MPa, it becomes hard. The Young's modulus is preferably 0.5 to 2.5 MPa, particularly preferably 0.6 to 2.0 MPa.

  The ophthalmic lens material of the present invention has low adhesiveness, is not adsorbed on the cornea during wearing, is safe, and is excellent in ease of operation. In addition, as described above, having an appropriate balance of strength, flexibility, and elasticity, while maintaining strength, has shape stability and is moderately flexible, and therefore has the effect of good stability during wearing. Can bring a good balance.

Examples 1-8 and Comparative Examples 1-6
An ophthalmic lens component obtained by mixing 0.2 parts by weight of 2-hydroxy-2-methyl-1-phenylpropan-1-one as a polymerizable initiator with respect to 100 parts by weight of the copolymerizable component shown in Table 1. And injected into a mold having a contact lens shape (made of polypropylene, corresponding to a contact lens having a diameter of about 14 mm and a center thickness of 0.1 mm). Next, the mold was irradiated with UV light for 10 minutes for photopolymerization to obtain a contact lens-shaped polymer. All these had a water content of less than 10%. In Examples 1 to 4, an amphiphilic component was blended in order to improve the compatibility of the blended components. The following evaluation was performed about the obtained polymer. The results are shown in Table 1.

In addition, the abbreviation in Table 1 shows the following compounds.
MAUS:

MTGA: methoxytriethylene glycol acrylate 2-MTA: 2-methoxyethyl acrylate 2-ETA: 2-ethoxyethyl acrylate POEA: 2-phenoxyethyl acrylate PHGA: phenylhexaethylene glycol acrylate MNGA: methoxynonyl ethylene glycol acrylate 2-EHA: 2-ethylhexyl acrylate DMAA: dimethylacrylamide LA: lauryl acrylate

(transparency)
If it was transparent when observed visually, it was rated as ○, and if it was cloudy, it was marked as ×.

(Adhesive)
In order to reproduce the slightly dry state of the wearing environment, the contact lens was sufficiently wetted with water, and then the water was absorbed with paper (semi-dry state). About the contact lens of the semi-dry state, adhesiveness was evaluated by the touch with fingers. If there was no stickiness on the surface, it was marked as ◯, and if there was stickiness on the surface, it was marked as x.

(Tensile test)
A tensile test was performed using an Instron universal material testing machine Model 4301, and the stress and elongation at break and Young's modulus were measured. Young's modulus was calculated from a stress-elongation curve. The sample was produced from the obtained polymer into a dumbbell shape having a total length of 12 mm and a distance between gauge points of 6 mm using a punching blade. The measurement environment was performed in physiological saline adjusted to a temperature of 35 ° C. at a tensile speed of 100 mm / min. In addition, about the comparative example 1, it was weak in intensity | strength and the sample for a tensile test could not be produced. Further, Comparative Examples 2, 5 and 6 were cloudy at the time of polymerization and were not transparent, so a tensile test was not performed.

  In Examples 1 to 8 where all of the compound (A), alkoxy group-containing acrylate (B), phenylalkyl acrylate or phenoxyalkyl acrylate (C) were copolymerized, the balance of transparency, strength, flexibility or elasticity was excellent. It was.

  In contrast, Comparative Example 1 in which the compound (A) was homopolymerized, and Comparative Example 3 in which the compound (A) and lauryl acrylate, which is not a regular component in the present invention, were copolymerized had high tackiness. Further, in Comparative Example 2 in which only the compound (A) and the alkoxy group-containing acrylate (B) were copolymerized, the mixture became cloudy, and in Comparative Example 4, the elongation was too small and the Young's modulus was large, so it was hard and damaged. It was easy. Further, in Comparative Examples 5 and 6 in which only the compound (A) and the phenylalkyl acrylate or the phenoxyalkyl acrylate (C) were copolymerized, the liquid became cloudy.

Claims (6)

Compound (A) having an ethylenically unsaturated group and a group containing a polydimethylsiloxane structure via a urethane bond, general formula (1):

(Wherein R ¹ is a methyl group or an ethyl group, and n is an integer of 1 to 6), or the general formula (2):

(Wherein R ¹ is a methyl group or an ethyl group, and n is an integer of 1 to 6) and the alkoxy group-containing acrylate (B) and the general formula (3):

Wherein R ² is an aromatic ring in which a hydrogen atom may be substituted with a substituent, X is an oxygen atom or a direct bond, and m is an integer of 1 to 5. Comprising a copolymer component comprising phenylalkyl acrylate or phenoxyalkyl acrylate (C),
An ophthalmic lens material having a stress in a tensile test at 35 ° C. of 0.1 to 10 MPa, an elongation of 10 to 300%, and a Young's modulus of 0.4 to 3.0 MPa. The ophthalmic lens material according to claim 1, wherein the copolymerization ratio of the compound (A) and the alkoxy group-containing acrylate (B) is 95: 5 to 30:70. The ophthalmic lens material according to claim 1 or 2, wherein the content of the phenylalkyl acrylate or phenoxyalkyl acrylate (C) in the copolymer component is 3 to 30% by weight. Compound (A) is represented by the general formula (4):
A ¹ -U ¹ -(-S ¹ -U ^2- ) _p -S ² -U ³ -A ² (4)
[In the formula, A ¹ represents the general formula (4-I):
^{Y 21 -Z 21 -R 31 - (} 4-I)
Wherein Y ²¹ is a (meth) acryloyl group, vinyl group or allyl group, Z ²¹ is an oxygen atom or a direct bond, R ³¹ is a direct bond or a linear, branched or aromatic ring having 1 to 12 carbon atoms. An alkylene group having
A ² represents the general formula (4-II):
-R ³⁴ -Z ²² -Y ²² (4-II)
(Wherein Y ²² is a (meth) acryloyl group, vinyl group or allyl group, Z ²² is an oxygen atom or a direct bond, R ³⁴ is a direct bond, or a linear, branched or aromatic ring having 1 to 12 carbon atoms. A group represented by an alkylene group) (Y ²¹ in the general formula (4-I) and Y ²² in the general formula (4-II) may be the same or different. ) And
U ¹ represents the general formula (4-III):
-X ²¹ -E ²¹ -X ²⁵ -R ^32- (4-III)
(Wherein, X ²¹ and X ²⁵ are each independently a direct bond, selected from oxygen atom and an alkylene glycol group, E ²¹ is -NHCO- group (however, in this case, X ²¹ is a direct bond, X ²⁵ Is an oxygen atom or an alkylene glycol group, E ²¹ forms a urethane bond with X ²⁵ , —CONH— group (where X ²¹ is an oxygen atom or an alkylene glycol group, and X ²⁵ is a direct bond, a divalent group E ²¹ is X ²¹ and forms a urethane bond) or a saturated or unsaturated aliphatic, from diisocyanate selected from the group consisting of alicyclic and aromatic (However, in this case, X ²¹ and X ²⁵ are each independently selected from the oxygen atom and an alkylene glycol group, E ²¹ forms two urethane bonds between X ²¹ and X ²⁵⁾ R ³² is a group represented by an alkylene group having a linear or branched chain having 1 to 6 carbon atoms),
S ¹ and S ² are each independently general formula (4-IV):

Wherein R ²³ , R ²⁴ , R ²⁵ , R ²⁶ , R ²⁷ and R ²⁸ are each independently an alkyl group having 1 to 6 carbon atoms, a fluorine-substituted alkyl group or a phenyl group, and K is 10 to 100 L is an integer of 0 or 1 to 90, and K + L is an integer of 10 to 100),
U ² represents the general formula (4-V):
^{-R 37 -X 27 -E 24 -X 28} -R 38 - (4-V)
(Wherein the alkylene group having a linear or branched R ³⁷ and R ³⁸ having 1 to 6 carbon atoms independently; each X ²⁷ and X ²⁸ is independently oxygen atom or an alkylene glycol group; E ²⁴ Is a divalent group derived from a diisocyanate selected from the group consisting of saturated or unsaturated aliphatic, alicyclic and aromatic groups (wherein E ²⁴ is two between X ²⁷ and X ²⁸ Which forms a urethane bond).
U ³ represents the general formula (4-VI):
^{-R 33 -X 26 -E 22 -X 22} - (4-VI)
(Wherein, R ³³ is selected from linear or branched chain alkylene group having, X ²² and X ²⁶ are each independently a direct bond, an oxygen atom and an alkylene glycol group having 1 to 6 carbon atoms, E ²² is —NHCO— group (wherein X ²² is an oxygen atom or an alkylene glycol group, X ²⁶ is a direct bond, E ²² forms a urethane bond with X ²² ), —CONH— group ( However, in this case, X ²² is a direct bond, X ²⁶ is an oxygen atom or an alkylene glycol group, and E ²² forms a urethane bond with X ²⁶ ), or a saturated or unsaturated aliphatic system, ring system and a divalent radical of a diisocyanate from selected from the group consisting of aromatic (However, in this case, X ²² and X ²⁶ are each independently selected from oxygen atom and an alkylene glycol group E ²² is a group represented by form two urethane bonds are) between X ²² and X ^26,
p represents 0 or an integer of 1 to 10. Or a polysiloxane macromonomer represented by the general formula (5):
A ¹ −U ¹ −T ¹ −U ⁴ − (− S ¹ −U ² −) _p −S ² −U ⁵ −T ² −U ³ −A ² (5)
[Wherein, A ¹ , A ² , U ¹ , U ² , U ³ , S ¹ , S ² , and p are the same as those in the general formula (4), and U ⁴ and U ⁵ represent U ¹ , U ³ and is the same. However, Y ²¹ and Y ²² in A ¹ and A ² are a (meth) acryloyl group, a vinyl group or an allyl group. T ¹ and T ² are represented by the general formula (5-I):
_{-Q- (CH 2 CHD-Q-)} q - (5-I)
(In the formula, D is a hydrogen atom, a methyl group or a hydroxyl group, Q is a direct bond or an oxygen atom, and q is an integer of 5 to 10,000), or General Formula (5-II):
-(M) _r- (5-II)
(In the formula, M is 1-methyl-3-methylene-2-pyrrolidone, N-vinyl-2-pyrrolidone, (meth) acrylic acid, (meth) acrylate, N, N-dimethyl (meth) acrylamide, Indicates a hydrophilic monomer unit selected from N, N-diethyl (meth) acrylamide, 2-hydroxyethyl (meth) acrylate, tetrahydrofuran, oxetane, oxazoline and 2-methacryloyloxyethyl phosphorylcholine, and is composed of hydrophilic monomer units The polymerization chain of the polymer may be linear or branched, and may be bonded in a random or block form, where r is an integer of 5 to 10,000) or a hydrophilic polymer-containing segment or hydrophilic It is a functional oligomer-containing segment. The ophthalmic lens material according to claim 1, 2 or 3. 5. The ophthalmic lens material according to claim 1, wherein the alkoxy group-containing acrylate (B) is (B1) methoxyethyl acrylate, (B2) ethoxyethyl acrylate, or (B3) methoxytriethylene glycol acrylate. The ophthalmic lens material according to claim 1, 2, 3, 4, or 5, wherein the phenylalkyl acrylate or phenoxyalkyl acrylate (C) is phenoxyethyl acrylate.