JP2005008786A - Water-containing material - Google Patents

Water-containing material Download PDF

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Publication number
JP2005008786A
JP2005008786A JP2003175941A JP2003175941A JP2005008786A JP 2005008786 A JP2005008786 A JP 2005008786A JP 2003175941 A JP2003175941 A JP 2003175941A JP 2003175941 A JP2003175941 A JP 2003175941A JP 2005008786 A JP2005008786 A JP 2005008786A
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Japan
Prior art keywords
water
weight
monomer composition
containing
containing material
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Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
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JP2003175941A
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Japanese (ja)
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JP2005008786A5 (en
Inventor
Takashi Makabe
隆 真壁
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Kuraray Medical Inc
クラレメディカル株式会社
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Priority to JP2003175941A priority Critical patent/JP2005008786A/en
Publication of JP2005008786A publication Critical patent/JP2005008786A/en
Publication of JP2005008786A5 publication Critical patent/JP2005008786A5/ja
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Abstract

An object of the present invention is to provide a water-containing material capable of obtaining a water-containing gel with little shape change due to temperature and little cloudiness.
SOLUTION: 99.0 to 99.9% by weight of 2-hydroxyethyl methacrylate and 0.1 to 1.0% of a monomer having at least two polymerizable groups based on the total weight of the monomer composition. A water-containing material obtained by polymerizing a monomer composition containing a proportion by weight.
[Selection figure] None

Description

[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a hydrous material. In the water-containing material of the present invention, a water-containing gel with less shape change due to temperature and less white turbidity can be obtained by hydrating and swelling the water-containing material. For example, soft contact lenses, intraocular lenses, artificial lenses, etc. Suitable as an ophthalmic lens, particularly suitable as a soft contact lens.
[0002]
[Prior art]
Hydrous materials are widely used as medical materials, in particular, soft contact lens materials, and in particular, polymers mainly composed of 2-hydroxyethyl methacrylate units are widely used (for example, Patent Documents 1 and 2). reference). It is known that the hydrated gel made of such a hydrated material changes its shape depending on the properties of the impregnated water (for example, pH, temperature, ionic strength, etc.). For example, in the case of a soft contact lens made of a water-containing material, the room temperature is at the time of storage, but immediately after wearing the soft contact lens, the temperature of the surface of the eye changes to about 35 ° C., and the influence of the shape of the soft contact lens Will change. As described above, since the shape change of the soft contact lens immediately after wearing causes a foreign body sensation, it has been desired to develop a hydrogel having little shape change due to temperature.
[0003]
In addition, 2-chloroethanol and methacrylic acid are used as starting materials for the synthesis of 2-hydroxyethyl methacrylate. In this synthesis, in addition to 2-hydroxyethyl methacrylate, which is the target product, 2-chloroethanol and methacrylic acid, which are starting materials, ethylene glycol dimethacrylate, alkylene glycol monomethacrylate or dimethacrylate, which are reaction byproducts, are included. It is. Although distillation is generally used as an industrial purification method, the boiling points of 2-hydroxyethyl methacrylate, which is the target product, and reaction by-products such as ethylene glycol dimethacrylate and alkylene glycol monomethacrylate are close to each other. Therefore, it was difficult to obtain 2-hydroxyethyl methacrylate having high purity by the distillation method. However, in recent years, with the improvement of industrial purification methods, the high-purity 2-hydroxyethyl methacrylate is supplied, and accordingly, a water-containing material having a high 2-hydroxyethyl methacrylate content is obtained. Became. However, the water-containing gel made of such a water-containing material has a problem that light scattering occurs and white turbidity is observed in the surface observation with the naked eye or a stereoscopic microscope.
[0004]
In order to solve such problems, a method of copolymerizing a crosslinking agent or a hydrophobic monomer with 2-hydroxyethyl methacrylate (for example, see Patent Document 3), 2-hydroxyethyl methacrylate containing a halogen compound is used. A method of radical polymerization of a monomer mixture containing a main component (see, for example, Patent Document 4) is known. However, in the hydrogel made of the hydrous material obtained from the former method, the elastic modulus is increased due to the copolymerization of the cross-linking agent and the hydrophobic monomer, and the shape recoverability is lowered and the hydrogel is brittle. In the hydrogel made of the hydrous material obtained by the latter method, there is a problem in safety because impurities are added.
[0005]
[Patent Document 1]
Japanese Patent Publication No.41-12629 [Patent Document 2]
Japanese Patent Publication No. 47-3735 [Patent Document 3]
JP-A-4-335007 [Patent Document 4]
JP-A-9-124715 [0006]
[Problems to be solved by the invention]
Therefore, an object of the present invention is to provide a water-containing material from which a water-containing gel with little change in shape due to temperature and little cloudiness can be obtained.
[0007]
[Means for Solving the Problems]
The present inventors paid attention to the content of 2-hydroxyethyl methacrylate and a monomer having at least two polymerizable groups in the monomer composition for obtaining a water-containing material, and converted 2-hydroxyethyl methacrylate to 99. From a water-containing material obtained by polymerizing a monomer composition containing 0.0 to 99.9% by weight and a monomer having at least two polymerizable groups in a proportion of 0.1 to 1.0% by weight It was found that the water-containing gel has less shape change due to temperature and less turbidity. In particular, a monomer composition containing 99.0 to 99.9% by weight of 2-hydroxyethyl methacrylate and 0.1 to 1.0% by weight of a monomer having at least two polymerizable groups. The present inventors have found that a water-containing material obtained by polymerization under a specific polymerization initiator and polymerization conditions has little white turbidity when formed into a water-containing gel and is suitable as an ophthalmic lens material such as a soft contact lens. It was.
[0008]
That is, the present invention provides 99.0 to 99.9% by weight of 2-hydroxyethyl methacrylate and 0.1 to 1 monomer having at least two polymerizable groups based on the total weight of the monomer composition. This is a water-containing material obtained by polymerizing a monomer composition containing 0.0% by weight.
[0009]
And in the said monomer composition, content of methacrylic acid with respect to the total weight is 0 to 0.4 weight%, and the water-containing material whose content of alkylene glycol monomethacrylate is 0 to 0.4 weight% It is.
[0010]
Furthermore, in any one of the above hydrous materials, the hydrous material is obtained by polymerizing using a polymerization initiator having a 10-hour half-life of 20 to 70 ° C.
[0011]
Furthermore, in any one of the above water-containing materials, the water-containing material is obtained by polymerization at a temperature of 40 to 150 ° C.
[0012]
Further, it is a soft contact lens made of any one of the above water-containing materials.
[0013]
DETAILED DESCRIPTION OF THE INVENTION
The present invention is described in detail below.
The hydrous material of the present invention contains 99.0 to 99.9% by weight of 2-hydroxyethyl methacrylate and 0.1% of a monomer having at least two polymerizable groups with respect to the total weight of the monomer composition. It is obtained by polymerizing a monomer composition containing at a ratio of ˜1.0% by weight. If the amount of 2-hydroxyethyl methacrylate contained in the monomer composition is less than 99.0% by weight, the hydrated gel made of the hydrated material becomes cloudy or changes in shape due to temperature. On the other hand, if it exceeds 99.9% by weight, the shape change due to the temperature of the water-containing gel made of the water-containing material becomes large. Therefore, the content of 2-hydroxyethyl methacrylate contained in the monomer composition is preferably 99.2 to 99.9% by weight from the viewpoint of shape change due to temperature of the hydrous gel and white turbidity, and 99.4%. More preferably, it is ˜99.9% by weight.
[0014]
As a method for obtaining 2-hydroxyethyl methacrylate having such a high purity, 2-hydroxyethyl methacrylate synthesized by an ordinary method may be purified by a known method, and the purification method is not particularly limited. Specific examples of the purification method include a distillation method, column chromatography, liquid high-speed chromatography, and the like. Of these, only one type may be used, or two or more types may be used in combination.
[0015]
In a hydrogel made of a hydrous material obtained by polymerizing a monomer composition having a high 2-hydroxyethyl methacrylate content, hydrogen bonds between hydroxyl groups partially contained in 2-hydroxyethyl methacrylate are formed. Therefore, microscopically, the water content tends to be non-uniform, and the transparency tends to be lowered. The present inventor has a monomer having 99.0 to 99.9% by weight of 2-hydroxyethyl methacrylate and at least two polymerizable groups in a range of 0.1 to 1.0.1% based on the total weight of the monomer composition. It has been found that in a water-containing material obtained by polymerizing a monomer composition containing 0% by weight, the water-containing gel is less turbid. When the content of the monomer having at least two polymerizable groups contained in the monomer composition is less than 0.1% by weight, the shape change due to the temperature of the water-containing gel made of the water-containing material becomes large. End up. On the other hand, if it exceeds 1.0% by weight, the hydrated gel made of the hydrated material becomes cloudy. Therefore, the content of the monomer having at least two polymerizable groups contained in the monomer composition is 0.1 to 0 from the viewpoint of shape change due to temperature and white turbidity of the hydrogel made of the hydrous material. 0.8 wt% is preferable, and 0.1 to 0.6 wt% is more preferable.
[0016]
As the monomer having at least two polymerizable groups, any monomer can be used as long as it has two or more polymerizable groups copolymerizable with 2-hydroxyethyl methacrylate. The polymerizable group is preferably at least one group selected from a (meth) acryloyloxy group, a vinyl group and an allyl group, and more preferably a (meth) acryloyloxy group. Examples of the monomer having at least two polymerizable groups include ethylene glycol di (meth) acrylate, 1,4-butanediol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, 1 , 9-nonanediol di (meth) acrylate, 1,10-decanediol di (meth) acrylate, alkylene glycol di (meth) acrylates such as neopentyl glycol di (meth) acrylate; diethylene glycol di (meth) acrylate, tri Polyalkylene glycol di (meth) acrylates such as ethylene glycol di (meth) acrylate, tetradecaethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, and polypropylene glycol di (meth) acrylate Allyl (meth) acrylate, trimethylolpropane tri (meth) acrylate, 2,2-bis [p- (γ-methacryloyloxy-β-hydroxypropoxy) phenyl] propane, methylenebis (meth) acrylamide, allyl (meth) Examples thereof include acrylate, vinyl (meth) acrylate, triallyl cyanurate, and the like. Only one type of these monomers having at least two polymerizable groups may be used, or two or more types may be used in combination. Among these, from the viewpoint of copolymerization with 2-hydroxyethyl methacrylate, monomers having at least two polymerizable groups include ethylene glycol dimethacrylate, 1,4-butanediol di (meth) acrylate, 1, It is preferable to use 6-hexanediol di (meth) acrylate, 1,9-nonanediol di (meth) acrylate, 1,10-decanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, ethylene glycol Dimethacrylate and 1,4-butanediol di (meth) acrylate are more preferred. When ethylene glycol dimethacrylate is contained as a reaction by-product in 2-hydroxyethyl methacrylate, which is the main component, in consideration of its content, at least a polymerizable group contained in the monomer composition is present. What is necessary is just to add this monomer so that the total content of the monomer which has two may be 0.1-1.0 weight%.
[0017]
Furthermore, when methacrylic acid which is an unreacted raw material in the process of synthesizing 2-hydroxyethyl methacrylate is contained in the monomer composition containing 2-hydroxyethyl methacrylate as the main component, The amount of protein (especially lysozyme) adheres to the water-containing gel made of the water-containing material and the shape change due to the temperature of the water-containing gel increases. It is preferably 0.4% by weight, and more preferably 0 to 0.1% by weight.
[0018]
Furthermore, in the case where alkylene glycol monomethacrylate is contained as a reaction by-product in the monomer composition mainly composed of 2-hydroxyethyl methacrylate, the water content of the water-containing material increases as the content increases. Since the shape change due to the temperature of the gel becomes large, the content of alkylene glycol monomethacrylate in the monomer composition is preferably 0 to 0.4% by weight, and preferably 0 to 0.3% by weight. It is more preferable.
[0019]
From the viewpoint of reducing the white turbidity of the water-containing gel made of the water-containing material, 99.0 to 99.9% by weight of 2-hydroxyethyl methacrylate and a polymerizable group in the molecule with respect to the total weight of the monomer composition. In the polymerization of a monomer composition containing 0.1 to 1.0% by weight of a monomer having at least two monomers, polymerization is performed using a polymerization initiator having a 10-hour half-life temperature of 20 to 70 ° C. It is preferable to do. As the polymerization initiator used in the present invention, any polymerization initiator having a 10-hour half-life temperature of 20 to 70 ° C. can be used. Specific examples thereof include 2,2′-azobis. Examples include azo polymerization initiators such as isobutyronitrile, 2,2′-azobisisobutyramide, dimethyl 2,2′-azobisisobutyrate, and peroxide polymerization initiators such as lauroyl peroxide and diisopropyl peroxydicarbonate. 1 type, or 2 or more types of these polymerization initiators can be used. From the viewpoint of the transparency of the water-containing gel obtained from the water-containing material, it is preferable to use a polymerization initiator having a 10-hour half-life of 25 to 69 ° C, and more preferably a polymerization initiator having a 25 to 68 ° C. . Moreover, the compounding quantity of a polymerization initiator is although it does not specifically limit, It is about 0.001-1.0 weight part with respect to 100 weight part of all the monomer compositions normally used for superposition | polymerization.
[0020]
The “10-hour half-life temperature” in the present invention refers to a temperature at which the polymerization initiator is reduced to the original half after 10 hours. That is, at the same polymerization temperature, a polymerization initiator having a higher 10-hour half-life temperature has a slower decomposition rate and a slower polymerization initiation reaction rate.
[0021]
Furthermore, the polymerization temperature of the monomer composition is preferably 40 to 150 ° C., more preferably 45 to 150 ° C., from the viewpoint of transparency of the hydrogel obtained from the hydrous material. In the polymerization, it is preferable to use a thermostatic bath, a hot-air circulation type heating device, etc. that can easily adjust the temperature.
[0022]
Moreover, the hydrogel which consists of a hydrous material of this invention may be colored. The method for obtaining a colored water-containing gel is not particularly limited, but a method in which a dye is mixed with a monomer composition and obtained from a pre-colored water-containing material, or a water-containing gel is obtained from a transparent (colorless) water-containing material. And then dyeing with a staining solution.
[0023]
When the water-containing material is used as an ophthalmic lens material, the turbidity of the water-containing gel obtained from the water-containing material is 10 mm in thickness in order to satisfy the optically required performance (low white turbidity and high transparency). Is preferably 10% or less, more preferably 9% or less. The turbidity of the water-containing gel obtained from the water-containing material means that the higher the numerical value, the more white the water-containing gel, and the smaller the value, the less the white turbid water-containing gel. Further, immediately after wearing the soft contact lens, the temperature of the water impregnated in the lens changes from room temperature to around 35 ° C., so that the shape of the soft contact lens changes. As described above, the shape change of the soft contact lens immediately after wearing causes a foreign body sensation. Therefore, when the water-containing material of the present invention is used as a soft contact lens, the shape change due to the temperature of the water-containing gel obtained from the water-containing material. Less is preferred. Specifically, in a soft contact lens having a diameter of 14.0 mm, a power of -3.00 diopter, and a center thickness of 0.10 mm, the shape change rate due to temperature is preferably 0.30% or less, and preferably 0.25% or less. It is more preferable that
[0024]
In the production of the soft contact lens comprising the water-containing material of the present invention, a method conventionally used for the production of a plastic contact lens, for example, (1) polymerization and molding of a monomer composition, and molding obtained (2) Fill the monomer composition into a mold having a mold cavity corresponding to the contact lens, and polymerize and mold in the mold. (3) A monomer composition is dropped onto a mold surface that rotates at high speed around a rotation axis, and the monomer composition is cast and diffused radially on the mold surface.・ Spin casting method for manufacturing contact lenses by molding, (4) Filling the mold with a monomer composition into a mold having a mold cavity capable of molding one side of the contact lens Polymerizing and molding, cutting the other side, none of the polished blank mold method of manufacturing a contact lens can adopt, not particularly limited.
[0025]
【Example】
Hereinafter, the present invention will be specifically described with reference to examples and the like, but the present invention is not limited thereto. In the following examples, the turbidity of a water-containing gel made of a water-containing material, the shape change rate depending on the temperature of a soft contact lens made of a water-containing material, and protein adhesion were measured or evaluated as follows.
[0026]
Turbidity of hydrogel:
(1) The water-containing gel made of the water-containing material obtained in the following Examples and Comparative Examples is cut to have a diameter of 15 mm and a thickness of 10 mm, and then the surface is polished to give a mirror finish. It is swollen to saturation in distilled water and used as a sample. With the sample immersed in distilled water at 25 ° C., using a haze meter (“MODEL TC-HIII type” manufactured by Tokyo Denshoku Co., Ltd.) and using a halogen lamp as the light source, the amount of incident light from the halogen lamp (T 1 ), the amount of light transmitted through the soft contact lens and distilled water (T 2 ), the amount of light diffused by distilled water (T 3 ), and the amount of light diffused by the soft contact lens and distilled water (T 4 ) The turbidity was determined from the formula (1) shown below.
[0027]
Turbidity (%) = {(T 1 / T 2 ) − (T 3 / T 4 )} × 100 (1)
[0028]
Soft contact lens shape change rate with temperature:
(1) The water-containing materials obtained in the following Examples and Comparative Examples were cut so as to have a diameter of 15 mm and a thickness of 10 mm, and this was cut and polished by a conventional method, and then a base curve of 8.7 mm, power − A soft contact lens having a diameter of 3.00 diopters, a diameter of 14.0 mm, and a center thickness of 0.10 mm was produced.
(2) The soft contact lens produced in the above (1) was immersed in physiological saline at 25 ° C. for one day and then the diameter of the lens was measured (D 1 ). Next, after the lens was immersed in 35 ° C. physiological saline, the change in diameter was measured over time, and the time until the shape was stabilized and the diameter (D 2 ) at that time were measured. The shape change rate due to temperature was calculated from the following equation (2). In addition, an enlargement projector (magnification ratio 10 times) was used for measuring the diameter.
[0029]
Shape change rate with temperature (%) = {(D 1 −D 2 ) / D 1 } × 100 (2)
[0030]
Protein adhesion:
(1) The water-containing materials obtained in the following Examples and Comparative Examples were cut so as to have a diameter of 15 mm and a thickness of 10 mm, and this was cut and polished by a conventional method, and then a base curve of 8.7 mm and a power of 0 A soft contact lens having a diopter, a diameter of 14.0 mm, and a center thickness of 0.20 mm was produced.
(2) The soft contact lens produced in the above (1) was worn on a white rabbit continuously for 2 days. After wearing, project the lens with a magnifying projector (magnification factor 10 times), observe the projected image, good if no dirt is found (○), good if a little dirt is seen (.DELTA.), The case where dirt was clearly recognized was evaluated as defective (x).
[0031]
Table 1 shows the contents of the abbreviations of the monomers and polymerization initiators used in the examples and comparative examples.
[0032]
[Table 1]
[0033]
[Examples 1 to 21]
(1) After adding the polymerization initiator shown in Table 2 to 10.0 g of the monomer composition shown in Table 2, it was put into a polypropylene test tube (capacity 20 ml) and sealed after nitrogen substitution. This was immersed in a constant temperature water bath at the temperature shown in Table 2 for 24 hours for polymerization, then transferred to a 100 ° C. hot-air circulating heating device and held for 2 hours to complete the polymerization. After cooling, the water-containing material was taken out from the test tube. In addition, the composition of the monomer composition shown in Table 2 shows a value obtained by analyzing the monomer composition by gas chromatography.
(2) Using the water-containing material obtained in (1) above, a hydrogel and a soft contact lens are prepared, and the turbidity of the hydrogel, the shape change rate depending on the temperature of the soft contact lens, and the protein adhesion are as described above. Measured or evaluated according to The results are shown in Table 3 below.
[0034]
[Comparative Example 1]
(1) After adding the polymerization initiator shown in Table 2 to 10.0 g of a general-purpose contact lens raw material (USAN registered product “Polymacon”) having the monomer composition shown in Table 2, a test tube made of polypropylene (capacity 20 ml) And sealed after nitrogen replacement. This was immersed in a constant temperature water bath at the temperature shown in Table 2 for 24 hours for polymerization, then transferred to a 100 ° C. hot-air circulating heating device and held for 2 hours to complete the polymerization. After cooling, the water-containing material was taken out from the test tube.
(2) Using the water-containing material obtained in (1) above, a hydrogel and a soft contact lens are prepared, and the turbidity of the hydrogel, the shape change rate depending on the temperature of the soft contact lens, and the protein adhesion are as described above. Measured or evaluated according to The results are shown in Table 3.
[0035]
[Comparative Examples 2 to 7]
Comparative Example 1 for the hydrogel and soft contact lens obtained by adding the polymerization initiator shown in Table 2 to 10.0 g of the monomer composition shown in Table 2 and performing the same treatment as in Comparative Example 1 above The same items were measured or evaluated. The results are shown in Table 3.
[0036]
[Table 2]
[0037]
[Table 3]
[0038]
From the results of Table 2 and Table 3 above, the monomer having 99.0 to 99.9% by weight of 2-hydroxyethyl methacrylate and at least two polymerizable groups based on the total weight of the monomer composition was determined. In Examples 1-21, which are monomer compositions contained at a ratio of 0.1 to 1.0% by weight, the turbidity of the hydrogel obtained from the hydrous material was also 10.0% or less. Moreover, the shape change rate with temperature was 0.30% or less, and protein adhesion was not recognized.
[0039]
On the other hand, the content of the monomer having at least two polymerizable groups and the content of alkylene glycol monomethacrylate with respect to the total weight of the monomer composition and the content of alkylene glycol monomethacrylate deviated from the scope of the present invention. The turbidity of the water-containing gel was 2.0% or less, and no protein adhesion was observed, but the shape change rate with temperature was 0.30% or more.
[0040]
On the other hand, Comparative Examples 2, 3 in which the content of 2-hydroxyethyl methacrylate in the monomer composition is out of the scope of the present invention and the content of methacrylic acid and / or alkylene glycol monomethacrylate is out of the scope of the present invention. Then, although the turbidity of the obtained water-containing gel was 2.0% or less, the shape change rate with temperature was 0.30% or more, and protein adhesion was clearly recognized.
[0041]
Further, in Comparative Examples 4 and 5 in which the content of the monomer having at least two polymerizable groups with respect to the total weight of the monomer composition is less than the range of the present invention, the shape change rate due to temperature is 0.30. % Or more.
[0042]
Further, in Comparative Examples 6 and 7 in which the content of the monomer having at least two polymerizable groups with respect to the total weight of the monomer composition is larger than the range of the present invention, the turbidity of the obtained hydrous gel is It was 10.0% or more.
[0043]
【The invention's effect】
According to the present invention, the monomer having 99.0 to 99.9% by weight of 2-hydroxyethyl methacrylate and at least two polymerizable groups is 0.1 to 1 with respect to the total weight of the monomer composition. Provided is a water-containing material obtained by polymerizing a monomer composition containing 0.0% by weight with little change in shape due to temperature of the water-containing gel obtained from the water-containing material and less cloudiness. .
And, 9 to 99.9% by weight of 2-hydroxyethyl methacrylate and 0.1 to 1.0% by weight of a monomer having at least two polymerizable groups based on the total weight of the monomer composition. In a water-containing material obtained by polymerizing a monomer composition containing at a ratio of 10% by using a polymerization initiator having a 10-hour half-life of 20 to 70 ° C, and polymerizing at a temperature of 40 to 150 ° C, From the water-containing material, a water-containing gel suitable for an ophthalmic lens material with little change in shape due to temperature and particularly low white turbidity is provided.

Claims (5)

  1. A ratio of 99.0 to 99.9% by weight of 2-hydroxyethyl methacrylate and 0.1 to 1.0% by weight of a monomer having at least two polymerizable groups based on the total weight of the monomer composition A hydrous material obtained by polymerizing a monomer composition contained in
  2. In the monomer composition, the content of methacrylic acid is 0 to 0.4% by weight with respect to the total weight of the monomer composition, and the content of alkylene glycol monomethacrylate is 0 to 0.4% by weight. The hydrous material according to claim 1, which is%.
  3. The water-containing material according to claim 1 or 2, which is obtained by polymerization using a polymerization initiator having a 10-hour half-life of 20 to 70 ° C.
  4. The water-containing material according to any one of claims 1 to 3, obtained by polymerization at a temperature of 40 to 150 ° C.
  5. The soft contact lens which consists of a hydrous material as described in any one of Claims 1-4.
JP2003175941A 2003-06-20 2003-06-20 Water-containing material Withdrawn JP2005008786A (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4891262B2 (en) * 2005-12-05 2012-03-07 株式会社メニコン Soft contact lens
WO2014002966A1 (en) * 2012-06-27 2014-01-03 株式会社メニコンネクト Colored contact lens and process for producing same

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4891262B2 (en) * 2005-12-05 2012-03-07 株式会社メニコン Soft contact lens
WO2014002966A1 (en) * 2012-06-27 2014-01-03 株式会社メニコンネクト Colored contact lens and process for producing same
JP5621118B2 (en) * 2012-06-27 2014-11-05 株式会社メニコンネクト Colored contact lens and manufacturing method thereof
KR20150011390A (en) * 2012-06-27 2015-01-30 가부시키가이샤 메니콘네쿠토 Colored contact lens and process for producing same
KR101645486B1 (en) 2012-06-27 2016-08-04 가부시키가이샤 메니콘네쿠토 Colored contact lens and process for producing same

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