JP3931089B2 - Method for producing soft contact lens comprising silicone hydrogel having hydrophilic surface and soft contact lens - Google Patents

Method for producing soft contact lens comprising silicone hydrogel having hydrophilic surface and soft contact lens Download PDF

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JP3931089B2
JP3931089B2 JP2002015630A JP2002015630A JP3931089B2 JP 3931089 B2 JP3931089 B2 JP 3931089B2 JP 2002015630 A JP2002015630 A JP 2002015630A JP 2002015630 A JP2002015630 A JP 2002015630A JP 3931089 B2 JP3931089 B2 JP 3931089B2
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contact lens
lens
surface
soft contact
hydrophilic monomer
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元 今福
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Hoyaヘルスケア株式会社
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Description

[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a method for producing a soft contact lens comprising a silicone hydrogel having a hydrophilic surface and a soft contact lens having a hydrophilic surface. More specifically, a method and a surface for producing a soft contact lens comprising forming a surface excellent in water wettability and wear resistance on a hydrous soft contact lens containing silicone as a component and having a moisture content in the range of 15 to 35%. Relates to a soft contact lens in which is made hydrophilic.
[0002]
[Prior art]
Clinical results indicate that when contact lenses are worn, the amount of oxygen supplied from the atmosphere decreases, which may result in corneal epithelial cell division inhibition and corneal thickening. Accordingly, attempts have been made to improve the oxygen permeability of materials in order to supply contact lenses with higher safety.
[0003]
In the case of a hydrous soft contact lens, it is known that the wear feeling is good due to the suppleness of the material, but its oxygen permeability is lower than that of a hard contact lens due to the moisture content of the lens. . For example, in the case of a hydrous soft contact lens, the oxygen permeability coefficient of a material with a moisture content of 80% is about 40 × 10 -11 (cm 2 / sec) · (mLO 2 / mL × mmHg), which is sufficient oxygen for the cornea It cannot be said that the quantity can be supplied. For this reason, contact lenses using siloxane macromers as lens components have been proposed in order to improve oxygen permeability in soft contact lenses. For example, Japanese Patent Application Laid-Open No. 2001-311917 discloses a soft contact lens material excellent in flexibility and oxygen permeability using a macromer having a dimethylsiloxane structure in the side chain. However, in general, when a silicone component is used as a lens material, the water wettability of the lens surface tends to be reduced, and as a result, dirt in the tear fluid component tends to adhere, and in some cases the wearing feeling is deteriorated. Sometimes.
[0004]
[Problems to be solved by the invention]
Under such circumstances, various surface treatment methods have been proposed for contact lenses in order to further improve the surface wettability.
Japanese Examined Patent Publication No. 62-37370 discloses a surface treatment method for a silicone resin contact lens using a low temperature plasma treatment using a hydrophilic monomer. In this method, after the hydrophilic monomer is vaporized, plasma is generated to form a hydrophilic polymer film on the lens surface. However, this method has problems such as requiring a very large apparatus and complicated setting of conditions for forming a film.
[0005]
JP-A-2-278224 discloses a method for hydrophilizing a surface of a hard contact lens. However, the treatment temperature during graft polymerization is low, the adhesion strength of the hydrophilic film after treatment is low, and durability is improved. It has the disadvantage of lacking.
JP-A-4-3116013 discloses a method for adding a cross-linking agent to a solution used for graft polymerization in order to increase the adhesion strength of a hydrophilic film with respect to surface treatment on a hard contact lens. However, this method can also be expected to improve durability by adding a cross-linking agent, and the durability can be expected. However, since the graft polymerization temperature is not so high, the effect of introducing the cross-linking agent is higher than expected. Not expensive.
[0006]
As described above, the conventional surface hydrophilization technique has many problems such as a large apparatus and lack of durability. Furthermore, even when viewed from the material side, most are silicone rubber non-hydrated soft contact lenses and hard contact lenses, and few are hydrogels containing silicone as a lens component.
[0007]
Accordingly, an object of the present invention is to provide a hydrous soft contact lens comprising a hydrogel containing silicone as a lens component, and a method for producing a product having a surface excellent in water wettability and wear resistance, and obtained by this method. It is an object of the present invention to provide a hydrous soft contact lens having a surface excellent in water wettability and wear resistance.
[0008]
In view of the prior art, the present inventor relates to a soft contact lens containing silicone as a component, a surface treatment method for forming a surface excellent in water wettability and wear resistance, and a softened surface softened surface. We made extensive studies on contact lenses. As a result, a contact lens-shaped copolymer in which hydroperoxide is formed on the surface by exposure to an oxygen atmosphere after low-temperature plasma treatment using an active gas and / or an inert gas is obtained at a temperature of 100 ° C. or higher as a hydrophilic monomer. It was found that a water-containing soft contact lens satisfying both water wettability and wear resistance can be obtained by dipping in an aqueous solution and subjecting the surface to graft polymerization, and the present invention has been completed. In the present invention, when the hydrophilic monomer aqueous solution immersion treatment is performed at a high temperature of 100 ° C. or higher, the hydroperoxide formed on the lens surface is efficiently decomposed and radicals are generated, thereby strengthening the hydrophilic monomer on the lens surface. It is considered that a hydrous soft contact lens that is graft polymerized and satisfies both water wettability and wear resistance can be obtained.
[0009]
[Means for Solving the Problems ]
In the present invention, a copolymer having a contact lens shape and comprising a hydrogel containing silicone is subjected to low-temperature plasma treatment using an active gas and / or an inert gas, exposed to an oxygen atmosphere, and at least 100 ° C. The present invention relates to a method for producing a soft contact lens having a hydrophilic surface, comprising immersing in an aqueous hydrophilic monomer solution at a temperature .
[0010]
DETAILED DESCRIPTION OF THE INVENTION
In the present invention, an object to be graft-polymerized is “a copolymer having a contact lens shape and comprising a hydrogel containing silicone”. Here, the “hydrogel containing silicone” and the “copolymer having a contact lens shape” may be a conventionally known material and contact lens, respectively. Such a material and a contact lens made of such a material are , for example, a material made of a macromer having a polysiloxane structure in a side chain and a contact lens described in JP-A-2001-311917 .
[0011]
In the production method of the present invention, a contact lens-shaped copolymer (hereinafter sometimes referred to as a contact lens material) is subjected to low-temperature plasma treatment using an active gas and / or an inert gas, and then exposed to an oxygen atmosphere. By this treatment, hydroperoxide is formed on the surface of the contact lens material. The plasma treatment for forming the hydroperoxide can be performed using a known method and apparatus such as low-frequency plasma, high-frequency plasma, and atmospheric pressure plasma. The treatment time is usually preferably 10 seconds to 10 minutes, but more preferably 20 seconds to 5 minutes in consideration of lens deterioration, work efficiency, and the like. The active gas and / or inert gas used in the low-temperature plasma treatment can be at least one selected from oxygen, nitrogen, air, hydrogen, helium and argon, and a mixed gas thereof may be used.
[0012]
Next, the lens material having hydroperoxide formed on the surface is immersed in a hydrophilic monomer solution. The hydrophilic monomer may be any hydrophilic monomer that can be grafted onto the surface of the lens on which the hydroperoxide has been formed. Preferred examples of such a hydrophilic monomer include 2-hydroxyethyl methacrylate, N, N-dimethylacrylamide, N-vinyl-2-pyrrolidone, and polyethylene glycol monomethacrylate. The hydrophilic monomer solution can be prepared by dissolving these hydrophilic monomers in distilled water from which oxygen has been sufficiently removed, physiological saline, or a storage solution for soft contact lenses. The concentration of the hydrophilic monomer is preferably 0.1 to 3% by weight, more preferably 0.2 to 1.5% by weight. If it is less than 0.1% by weight, sufficient water wettability cannot be imparted to the lens surface, and if it exceeds 3% by weight, the hydrophilic film formed on the lens may become too thick, which may be undesirable.
[0013]
In the production method of the present invention, the graft polymerization treatment is performed by immersing the lens material in the hydrophilic monomer solution at a temperature of 100 ° C. or higher. The upper limit of the immersion treatment temperature is a temperature that the lens can withstand, and the immersion treatment temperature is preferably 100 to 130 ° C. If the temperature is lower than 100 ° C., the lens surface and the hydrophilic monomer do not react strongly, so that the water wettability of the lens surface lacks durability. When the temperature exceeds 130 ° C., the lens material may cause deterioration such as hydrolysis. The graft polymerization treatment time may be within a range where the lens surface and the hydrophilic monomer react with each other, and is usually 20 minutes to 3 hours. However, considering the working efficiency, 30 minutes to 2 hours are preferable.
[0014]
In order to further increase the reactivity between the contact lens material and the hydrophilic monomer, a water-soluble peroxide or a water-soluble polymerization initiator can be further added to the hydrophilic monomer solution. Specific examples of the water-soluble peroxide and the water-soluble polymerization initiator include ammonium persulfate, potassium persulfate, sodium persulfate, potassium peroxymonosulfate, sodium peroxymonosulfate, and 2,2-azobis (2-amidinopropane) di. Hydrochloride and the like.
[0015]
Furthermore, in the present invention, in order to increase the graft density of the hydrophilic monomer on the contact lens surface and further improve the durability of the lens surface, a crosslinking monomer such as polyethylene glycol di (meth) acrylate is added to the hydrophilic monomer solution. You can also
[0016]
The soft contact lens obtained by the present invention comprises a soft contact lens substrate made of a hydrogel containing silicone and a hydrophilic graft polymerized layer provided on the surface thereof, and has a moisture content in the range of 15 to 35%. Includes a lens. Soft contact lens base made of a hydrogel comprising silicone is of a known, as described above, for example, described in JP 2001-311917 and the like described above. Further, the hydrophilic graft polymerization layer is formed by the method described in the above production method.
[0017]
The water content of the soft contact lens can be appropriately controlled, for example, by selecting the content of the hydrophilic component contained in the contact lens material, and is preferably in the range of 15 to 35%. If the water content is 15% or more, good flexibility can be obtained, and if it is 35% or less, oxygen permeability can be increased without depending on the water content, which is preferable. The water content of the soft contact lens is preferably in the range of 25 to 35%.
[0018]
【Example】
EXAMPLES Hereinafter, although an Example demonstrates this invention further, this invention is not limited to a following example.
[0019]
1. Example A of making a contact lens as a substrate
Synthesis of Macromer In a three-necked flask, 8.88 g of isophorone diisocyanate, 0.025 g of dibutyltin dilaurate as a catalyst and 45 mL of methylene chloride were placed and stirred under a nitrogen stream. Next, 20 g of α-butyl-ω- [3- (2,2- (dihydroxymethyl) butoxy) propyl] polydimethylsiloxane was precisely weighed and dropped into the flask over about 3 hours to be reacted. After reacting at room temperature for 48 hours, 0.025 g of dibutyltin dilaurate and 23.3 g of polyethylene glycol monomethacrylate (PE-350) were precisely weighed and dropped into the flask over about 30 minutes. The mixture was covered with aluminum foil and stirred until the absorption band (2260 cm −1 ) derived from isocyanate disappeared in IR (infrared absorption spectrum) analysis (reaction for about 48 hours at room temperature). Further methylene chloride was added to this solution, followed by washing with a large amount of water, dehydration and filtration, and then the solvent was distilled off to obtain a macromer having a number average molecular weight of 2,000 (polystyrene equivalent).
[0020]
Preparation of contact lenses About 5 g of the siloxane macromonomer obtained in Example A, about 9 g of tris (trimethylsiloxy) -γ-methacryloxypropylsilane, about 6 g of N, N-dimethylacrylamide, 1-anilino-4- (4- A monomer mixture was prepared by mixing about 0.0016 g of vinylbenzyl) aminoanthraquinone and about 0.12 g of phenylbis (2,4,6-trimethylbenzoyl) phosphine oxide at room temperature for about 20 hours. Next, the monomer mixture is filled into a contact lens-shaped mold made of polypropylene, and the upper mold and the lower mold are assembled, and then irradiated with ultraviolet rays to visible rays (380 to 450 nm) of about 30 mW / cm 2 for 20 minutes. The polymerization was completed. After completion of the polymerization, the polymer was taken out from the mold and a contact lens was obtained.
[0021]
Example A-1
Graft Polymerization Using N, N-Dimethylacrylamide The contact lens obtained in Example A-1 was placed in a plasma polymerization apparatus, and was 2 at a frequency of 13.56 MHz and a discharge power of 40 W in an air atmosphere with a degree of vacuum of 0.6 torr. Low temperature plasma treatment for minutes. Next, about 0.5 g of N, N-dimethylacrylamide (DMAA) was dissolved in 99.5 g of distilled water and mixed well. The low-temperature plasma-treated lens taken out from the plasma polymerization apparatus into the air was immersed in this solution and sealed, and then treated at 121 ° C. for 60 minutes to graft-polymerize the surface. For graft polymerized soft contact lenses, water wettability (contact angle measurement), surface hydrophilic film durability (scrubbing durability test), lipid contamination, and optical parameter measurement are performed by the following measurement methods. The results are shown in Tables 1 and 2. As shown in Table 1, the graft-polymerized lens of the present invention was excellent in water wettability and durability, and had a very low lipid adhesion amount. Further, as shown in Table 2, no change was observed in the optical parameters before and after graft polymerization, which was satisfactory as a method for producing a surface-treated soft contact lens.
[0022]
(A) Contact angle measurement After wiping off the moisture on the lens surface, the lens was attached to a holding table, and the contact angle was measured by a liquid method using distilled water.
[0023]
(B) Rubbing durability test The lens was placed on the palm, and the front and back surfaces of the lens were scrubbed with a soft contact lens cleaning solution, and then rinsed thoroughly with distilled water. This operation was repeated once and the washing operation was repeated. After the number of washing times 10, 20, 30, 40,..., And 90 times, contact angle measurement was performed by the method shown in the above a) to evaluate the durability of the surface hydrophilic film.
[0024]
(C) Evaluation of lipid contamination 0.012 g of oleic acid, 0.012 g of linoleic acid, 0.012 g of palmitic acid, 0.162 g of tripalmitin, 0.04 g of cetyl alcohol, 0.162 g of cetyl myristate, 0.016 g of cholesterol, 0.016 g of cholesterol palmitate and 0.566 g of egg yolk lecithin are precisely weighed, dissolved by heating and dissolved in a phosphate / borate buffer (0.18 g of sodium chloride, 0.1 g of potassium dihydrogen phosphate, 0.1% of sodium tetraborate). 238 g) 20 mL was added and suspended using an ultrasonic homogenizer. After filtering this liquid using glass fiber filter paper, the suspension was further diluted 10-fold with a phosphate / borate buffer, adjusted to pH 7.0 with 1N hydrochloric acid, and used as artificial eye oil.
[0025]
The lenses were transferred one by one to a glass vial containing 2.0 mL of artificial eye grease, and the vial was held for 5 hours while permeating in a constant temperature shaker set at 37 ° C. After 5 hours, the lens was taken out, rinsed with distilled water, dried, placed in 1 mL of an organic mixed solvent of ethanol: diethyl ether = 3: 1, and kept for 4 hours to obtain an extract. The total amount of lipid adhered to each lens of the obtained extract was calculated using the sulfuric acid / phosphoric acid / vanillin method.
[0026]
(D) Optical parameter measurement Lens parameters were measured before and after the graft polymerization treatment, and the presence or absence of changes before and after the treatment was confirmed.
[0027]
Example A-2
Graft polymerization was performed under the same processing conditions as in Example A- 1 , except that the plasma polymerization conditions were set to 4 minutes at a frequency of 13.56 MHz and a discharge power of 40 W in an air atmosphere with a degree of vacuum of 0.6 torr. The lens evaluation results are shown in Tables 1 and 2.
[0028]
Example A-3
The graft polymerization was performed under the same treatment conditions as in Example A-2 except that the graft polymerization conditions were 110 ° C. and 30 minutes. The lens evaluation results are shown in Tables 1 and 2.
[0029]
Example A-4
Graft polymerization was carried out under the same treatment conditions as in Example A-2 except that about 1 g of DMAA was dissolved in 99 g of distilled water and sufficiently mixed with the monomer solution used for graft polymerization. The lens evaluation results are shown in Tables 1 and 2.
[0030]
Example A-5
The graft polymerization was carried out under the same treatment conditions as in Example A-2 except that the monomer solution used for the graft polymerization was changed to the following.
About 0.5 g of DMAA and about 0.1 g of 2,2-azobis (2-amidinopropane) dihydrochloride were dissolved in 99.5 g of distilled water and mixed well. The lens evaluation results are shown in Tables 1 and 2.
[0031]
Example B-1
Graft Polymerization Using Polyethylene Glycol Monomethacrylate The contact lens obtained in Example A-1 was placed in a plasma polymerization apparatus and was cooled for 1 minute at a frequency of 13.56 MHz and a discharge power of 70 W in an oxygen atmosphere with a degree of vacuum of 0.5 torr. Plasma treatment was performed. Next, about 1.25 g of polyethylene glycol monomethacrylate (PE-7) having a polyethylene glycol chain repeating unit of about 7 was dissolved in 98.75 g of distilled water and mixed well. The low-temperature plasma-treated lens taken out from the plasma polymerization apparatus in the air was immersed in this solution, sealed, and then treated at 121 ° C. for 40 minutes to subject the surface to graft polymerization. The graft-polymerized soft contact lenses were measured for water wettability, surface hydrophilic membrane durability and lipid contamination, and parameters by the same measurement method as described above. The results are shown in Tables 1 and 2. As shown in Table 1, the graft-polymerized lens of the present invention was excellent in water wettability and durability, and had a very low lipid adhesion amount. Further, as shown in Table 2, no change was observed in the optical parameters before and after graft polymerization, which was satisfactory as a method for producing a surface-treated soft contact lens.
[0032]
Example B-2
The graft polymerization was performed under the same grafting conditions as in Example B-1, except that the graft polymerization conditions were 110 ° C. and 40 minutes. The lens evaluation results are shown in Tables 1 and 2.
[0033]
Example B-3
Graft polymerization was carried out under the same processing conditions as in Example B-1, except that about 1.5 g of PE-7 was dissolved in 98.5 g of distilled water and sufficiently mixed with the monomer solution used for graft polymerization. Was given. The lens evaluation results are shown in Tables 1 and 2.
[0034]
Example C-1
Graft polymerization using N-vinyl-2-pyrrolidone The contact lens obtained in Example A-1 was put in a plasma polymerization apparatus, and the frequency was 13.56 MHz and the discharge power was 50 W in an air atmosphere with a degree of vacuum of 0.8 torr. Low temperature plasma treatment was performed for 3 minutes. Next, about 0.5 g of N-vinyl-2-pyrrolidone and about 0.1 g of 2,2-azobis (2-amidinopropane) dihydrochloride were dissolved in 99.5 g of distilled water and mixed well. The low-temperature plasma-treated lens taken out from the plasma polymerization apparatus into the air was immersed in this solution and sealed, and then treated at 110 ° C. for 50 minutes to graft-polymerize the surface. The graft-polymerized soft contact lenses were measured for water wettability, surface hydrophilic membrane durability and lipid contamination, and parameters by the same measurement method as described above. The results are shown in Tables 1 and 2. As shown in Table 1, the graft-polymerized lens of the present invention was excellent in water wettability and durability, and had a very low lipid adhesion amount. Further, as shown in Table 2, no change was observed in the optical parameters before and after graft polymerization, which was satisfactory as a method for producing a surface-treated soft contact lens.
[0035]
Example C-2
Graft polymerization was performed under the same processing conditions as in Example C-1, except that the plasma polymerization conditions were set to 2 minutes at a frequency of 13.56 MHz and a discharge power of 60 W in an air atmosphere with a degree of vacuum of 0.5 torr. The lens evaluation results are shown in Tables 1 and 2.
[0036]
Comparative Example 1
The contact lens obtained in Example A-1 was placed in a plasma polymerization apparatus and subjected to low-temperature plasma treatment for 2 minutes at a frequency of 13.56 MHz and a discharge power of 40 W in an air atmosphere with a degree of vacuum of 0.6 torr. Next, it was immersed in a 10% by weight aqueous solution containing acrylamide and N, N′-methylenebisacrylamide (molar ratio 9: 1), sufficiently deaerated, then sealed and sealed in a constant temperature water bath at 60 ° C. for 80 minutes. Graft polymerization was performed. Although the obtained lens had initial hydrophilicity, it had poor rubbing durability.
[0037]
Comparative Example 2
The contact lens obtained in Example A-1 was placed in a plasma polymerization apparatus and subjected to low-temperature plasma treatment for 2 minutes at a frequency of 13.56 MHz and a discharge power of 40 W in an air atmosphere with a degree of vacuum of 0.6 torr. Next, it was immersed in a 0.5% by weight aqueous solution containing DMAA, sufficiently deaerated, sealed, and graft-polymerized in a constant temperature water bath at 50 ° C. for 60 minutes. Although the obtained lens had initial hydrophilicity, it had poor rubbing durability.
[0038]
Comparative Example 3
The contact lens obtained in Example A-1 was placed in a plasma polymerization apparatus, and plasma-treated for 4 minutes at a frequency of 13.56 MHz and a discharge power of 50 W in an air atmosphere with a degree of vacuum of 0.6 torr. Next, it was immersed in a 1.25% by weight aqueous solution containing PE-7, sufficiently deaerated, sealed, and graft-polymerized in a constant temperature water bath at 80 ° C. for 60 minutes. Although the obtained lens had initial hydrophilicity, it had poor rubbing durability.
[0039]
Comparative Example 4
The contact lens obtained in Example A-1 was placed in a plasma polymerization apparatus, and plasma-treated for 4 minutes at a frequency of 13.56 MHz and a discharge power of 50 W in an air atmosphere with a degree of vacuum of 0.6 torr. Next, it was immersed in a 0.5 wt% aqueous solution containing NVP, sufficiently deaerated, sealed, and graft-polymerized in a constant temperature water bath at 80 ° C. for 60 minutes. Although the obtained lens had initial hydrophilicity, it had poor rubbing durability.
[0040]
Comparative Example 5 (in the case of hard contact lens material)
20 g (50% by weight) of tris (trimethylsiloxy) -γ-methacryloxypropylsilane (RAVINOL), 20 g (50% by weight) of 2,2,2-trifluoroethyl methacrylate (3FMA), 0.8 g of ethylene glycol dimethacrylate ( 2% by weight with respect to the total amount of RAVINOL and 3FMA) and 0.14 g of azobisisobutyronitrile (AIBN) (0.35% by weight with respect to the total amount of RAVINOL and 3FMA) and stirred well A monomer mixture was prepared. This monomer mixture was placed in a polyethylene pipe and polymerized at 45 ° C. for 120 hours. After the polymerization, a rod-shaped polymer was taken out from the pipe and dried overnight in a dryer at 110 ° C. A hard contact lens was produced from the obtained polymer.
[0041]
This hard contact lens was put in a plasma polymerization apparatus, and was plasma-treated for 2 minutes at a frequency of 13.56 MHz and a discharge power of 50 W in an air atmosphere with a vacuum degree of 0.6 torr. Next, it was immersed in a 0.5% by weight aqueous solution containing DMAA, sufficiently deaerated, then sealed and graft polymerized at 80 ° C. for 60 minutes. The base curve of the obtained lens was deformed and could not be used as a contact lens.
[0042]
[Table 1]
[0043]
[Table 2]
[0044]
As shown in Table 1, the lenses whose surfaces were graft-polymerized at a relatively low temperature as in Comparative Examples 1 to 4 were poor in scrubbing durability, although they had initial hydrophilicity. . Further, when the surface treatment was performed by the method of the present invention using a hard contact lens material as in Comparative Example 5, the treated lens was deformed and could not be used as a contact lens.
[0045]
On the other hand, the lenses exemplified in the examples all have hydrophilic membranes with excellent durability and are difficult to adhere lipid stains. This is because the surface treatment in the production method of the present invention is a treatment at a high temperature of 100 ° C. or higher, and the hydroperoxide formed on the lens surface is efficiently decomposed to generate radicals, whereby hydrophilic monomers are formed on the lens surface. It can be said that this is a strong graft polymerization effect.
[0046]
【The invention's effect】
ADVANTAGE OF THE INVENTION According to this invention, the soft contact lens which has the surface excellent in water wettability and abrasion resistance, especially the soft contact lens which consists of hydrogel which contains silicone as a lens component can be provided.

Claims (4)

  1. Has a contact lens shape, and a copolymer comprising a hydrogel comprising silicone and low-temperature plasma treatment using an inert gas and / or inert gas, by subsequent曝Succoth in an oxygen atmosphere, the copolymer surface To form a hydroxy peroxide,
    Soft contact having a hydrophilic surface, comprising hydrophilizing the copolymer surface by immersing the copolymer in a hydrophilic monomer-containing aqueous solution and graft polymerizing the hydroxy peroxide and the hydrophilic monomer. A method of manufacturing a lens,
    The copolymer consists of a macromer having a polysiloxane structure in the side chain,
    The said graft polymerization is a manufacturing method of the soft contact lens which has a hydrophilized surface performed by the energy obtained by making the said hydrophilic monomer containing aqueous solution the temperature of 100 degreeC or more .
  2. The production method according to claim 1, wherein the active gas and / or the inert gas is at least one selected from oxygen, nitrogen, air, hydrogen, helium, and argon.
  3. The production method according to claim 1 or 2, wherein the hydrophilic monomer is 2-hydroxyethyl methacrylate, N, N-dimethylacrylamide, N-vinyl-2-pyrrolidone, or polyethylene glycol monomethacrylate.
  4. The manufacturing method of any one of Claims 1-3 in which hydrophilic monomer containing aqueous solution further contains a water-soluble peroxide, a water-soluble polymerization initiator, and / or a crosslinkable monomer.
JP2002015630A 2002-01-24 2002-01-24 Method for producing soft contact lens comprising silicone hydrogel having hydrophilic surface and soft contact lens Active JP3931089B2 (en)

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US7426993B2 (en) * 2005-08-09 2008-09-23 Coopervision International Holding Company, Lp Contact lens package
US7625598B2 (en) * 2006-12-15 2009-12-01 Bausch & Lomb Incorporated Silicone contact lenses with wrinkled surface
JP5253851B2 (en) * 2008-03-18 2013-07-31 株式会社シード Ophthalmic lens and method for manufacturing ophthalmic lens
JP5927014B2 (en) 2012-04-18 2016-05-25 Hoya株式会社 Silicone hydrogel soft contact lens with wettable surface
JP2013235034A (en) * 2012-05-02 2013-11-21 Menicon Co Ltd Manufacturing method of surface treatment resin molding, and surface treatment resin molding

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