JPH04180013A - Production of contact lens - Google Patents
Production of contact lensInfo
- Publication number
- JPH04180013A JPH04180013A JP30931990A JP30931990A JPH04180013A JP H04180013 A JPH04180013 A JP H04180013A JP 30931990 A JP30931990 A JP 30931990A JP 30931990 A JP30931990 A JP 30931990A JP H04180013 A JPH04180013 A JP H04180013A
- Authority
- JP
- Japan
- Prior art keywords
- base material
- lens base
- methacrylate
- contact lens
- treatment
- Prior art date
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 239000000463 material Substances 0.000 claims abstract description 24
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims abstract description 10
- -1 alkyl methacrylate Chemical compound 0.000 claims abstract description 10
- 239000000178 monomer Substances 0.000 claims abstract description 7
- 238000006116 polymerization reaction Methods 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 2
- 238000007599 discharging Methods 0.000 claims 1
- 238000011282 treatment Methods 0.000 abstract description 15
- 208000028659 discharge Diseases 0.000 abstract description 7
- 229920001577 copolymer Polymers 0.000 abstract description 5
- 230000010355 oscillation Effects 0.000 abstract description 4
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 abstract description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 abstract description 2
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 abstract 1
- 238000007789 sealing Methods 0.000 abstract 1
- 238000010559 graft polymerization reaction Methods 0.000 description 13
- 239000000243 solution Substances 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- IMDPTYFNMLYSLH-UHFFFAOYSA-N 3-silylpropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC[SiH3] IMDPTYFNMLYSLH-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 210000004087 cornea Anatomy 0.000 description 1
- 238000003851 corona treatment Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229940127554 medical product Drugs 0.000 description 1
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
Abstract
Description
【発明の詳細な説明】
[産業上の利用分野]
本発明は表面の濡れ性を恒久的に維持し、装用感に優れ
るハードコンタクトレンズを獲得するための製造方法に
関する。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a manufacturing method for obtaining a hard contact lens that permanently maintains surface wettability and is comfortable to wear.
[従来の技術]
コンタクトレンズ装用時の異物感を減少させて装用感を
向上させるには、角膜とレンズ表面とのなじみを良くす
ることが重要である。具体的な方法としては、コンタク
トレンズ表面に親水性子ツマ−であるアクリルアミドを
グラフト重合することにより、レンズ表面の濡れ性を向
上させることがあげられる。ところで、表面グラフト重
合の処理工程を簡単に説明すると、まず放電処理等を施
したコンタクトレンズ基材を千ツマー溶液中に浸漬する
。次に溶存酸素を除いた後これに加温等を施し重合処理
を行う。従来、この重合時には、重合容器は静止した状
態で処理を行っていた。[Prior Art] In order to reduce the feeling of a foreign body when wearing a contact lens and improve the feeling of wearing it, it is important to improve the compatibility between the cornea and the lens surface. A specific method is to improve the wettability of the lens surface by graft polymerizing acrylamide, which is a hydrophilic child, onto the surface of the contact lens. By the way, to briefly explain the treatment process of surface graft polymerization, first, a contact lens base material that has been subjected to an electric discharge treatment or the like is immersed in a solution of 100% water. Next, after removing dissolved oxygen, this is heated and subjected to polymerization treatment. Conventionally, during this polymerization, the polymerization container was kept stationary.
[発明が解決しようとする課題]
しかし、前述の従来技術では、重合処理中に千ツマー溶
液中の濃度分布が不均一になってしまい、これが原因で
コンタクトレンズ基材表面のグラフト処理状態も均一性
に欠き、また表面の一部に白濁が生じてしまう場合もあ
った。[Problems to be Solved by the Invention] However, in the above-mentioned conventional technology, the concentration distribution in the Senzummer solution becomes non-uniform during the polymerization process, which causes the grafting state on the surface of the contact lens base material to become non-uniform. In some cases, the surface was cloudy.
そこで、本発明は従来のこのような問題点を解決するた
め、その目的とするところは、グラフト重合時のモノマ
ー溶液の不均一性をなくし、均質な表面グラフト処理を
可能とするコンタクトレンズの製造方法を提供すること
にある。Therefore, in order to solve these conventional problems, the present invention aims to eliminate the non-uniformity of the monomer solution during graft polymerization and manufacture a contact lens that enables homogeneous surface grafting treatment. The purpose is to provide a method.
[課題を解決するための手段]
上記課題を解決するために本発明のコンタクトレンズの
製造方法は、少なくとも、アルキルメタクリレート、シ
ロキサニルメタクリレート(式中XおよびYはC+ −
C6のアルキル基および基からなる群から選ばれ、Zは
構造式
%式%]
をもっ基であり、AはC1〜C5のアルキル基を示す。[Means for Solving the Problems] In order to solve the above problems, the method for manufacturing a contact lens of the present invention comprises at least alkyl methacrylate, siloxanyl methacrylate (wherein X and Y are C + −
It is selected from the group consisting of C6 alkyl groups and groups, Z is a group having the structural formula % Formula %], and A represents a C1 to C5 alkyl group.
k、 1. m、 nはOl又は正の整数を示す
。)との共重合物であるメタクリル酸のエステル化合物
のポリマーを原材料とし六コンタクトレンズ基材に関し
、 (a)その表面を常圧あるいは減圧下で放電処理す
る工程と、 (b)前記基材をアクリルアミドを主成分
とする千ツマー溶液に浸漬する工程と、 (C)前記基
材表面にアクリルアミドをグラフト重合する工程とから
成るコンタクトレンズの製造方法において、前記(C)
工程中の重合処理を揺動を与えながら行うことを特徴と
する。k, 1. m and n represent Ol or a positive integer. 6) Concerning a contact lens base material made from a polymer of an ester compound of methacrylic acid, which is a copolymer with A method for producing a contact lens comprising the steps of: immersing in a solution containing acrylamide as a main component; and (C) graft polymerizing acrylamide onto the surface of the base material.
It is characterized by performing the polymerization treatment during the process while applying shaking.
なお、代表的なメタクリル酸のエステル化合物には以下
のものがあげられる。In addition, the following are listed as typical ester compounds of methacrylic acid.
ペンタメチルジシロキサニルメチルメタクリレート
トリス(トリメチルシロキシ)−γ−メタクリルオキシ
プロピルシラン
CH3
CH3−3i−CH3
CH3−5i−CH3
CH3
イソブチルヘキサメチルトリシロキサニルメチルメタク
リレート
以下、実施例により本発明の詳細を示す。Pentamethyldisiloxanyl methyl methacrylate Tris(trimethylsiloxy)-γ-methacryloxypropylsilane CH3 CH3-3i-CH3 CH3-5i-CH3 CH3 Isobutylhexamethyltrisiloxanyl methyl methacrylate The details of the present invention are described below with reference to Examples. shows.
[実施例1]
架橋剤であるN、N’−メチレンビスアクリルアミド2
.5g、アクリルアミド10gを蒸留水に溶かして10
0m1とし、千ツマー水溶液を調製した。[Example 1] Crosslinking agent N,N'-methylenebisacrylamide 2
.. Dissolve 5g of acrylamide and 10g of acrylamide in distilled water.
0 ml, and an aqueous solution of 1,000 ml was prepared.
グラフト重合は次のようにして行なった。メチルメタク
ワレート60wt%、 トリス(トリメチルシロキシ)
シリルプロピルメタクリレート35wt%、2−ヒドロ
キシエチルメタクリレート5wt%の共重合物よりなる
コンタクトレンズ基材を用意した。放電装置(電極間6
センチメードル、電極間電圧270ボルト、周波数60
ヘルツ)にレンズ基材を設置して、0.04トールのア
ルゴン雰囲気中で5秒間グロー放電処理をした。放電処
理したレンズ基材を空気中にさらした後、これを試験管
に入れ、前記モノマー水溶液をレンズ基材が十分浸かる
量加えた。これを真空系に接続し、管内を脱気し、その
まま真空封管を行った。この状態で試験管を往復様どう
機(E’P−1、大洋サービスセンター株式会社製)に
挿入し揺動を与えながら80°Cの恒温下で60分間基
材表面へのグラフト重合処理を行った。重合駐了後、処
理表面の白濁の有無を光学顕微鏡にて評価した。尚、往
復様とう機の揺動条件(揺動周期、振幅)を第1表の如
く設定し、6試料(試料1〜6)について検討した。Graft polymerization was carried out as follows. Methyl methacquarate 60wt%, Tris (trimethylsiloxy)
A contact lens base material made of a copolymer of 35 wt% silylpropyl methacrylate and 5 wt% 2-hydroxyethyl methacrylate was prepared. Discharge device (between electrodes 6
Centimeters, voltage between electrodes 270 volts, frequency 60
The lens base material was placed in a 0.04 Torr argon atmosphere and subjected to glow discharge treatment for 5 seconds. After the discharge-treated lens base material was exposed to the air, it was placed in a test tube, and the monomer aqueous solution was added in an amount sufficient to submerge the lens base material. This was connected to a vacuum system, the inside of the tube was degassed, and the tube was then vacuum sealed. In this state, the test tube was inserted into a reciprocating machine (E'P-1, manufactured by Taiyo Service Center Co., Ltd.) and subjected to graft polymerization treatment on the substrate surface for 60 minutes at a constant temperature of 80°C while shaking. went. After completion of polymerization, the presence or absence of cloudiness on the treated surface was evaluated using an optical microscope. The swinging conditions (oscillation period, amplitude) of the reciprocating machine were set as shown in Table 1, and six samples (samples 1 to 6) were studied.
一方比較のkめ従来通り揺動を与えずに表面グラフト重
合処理を行ったものについても検討した(比較例1〜6
)。On the other hand, for comparison, we also investigated the surface graft polymerization treatment without shaking as before (Comparative Examples 1 to 6).
).
第1表より明らかなように、グラフト重合吟に揺動を与
えたもの(試料1〜6)については全て表面状態は良好
で白濁等は皆無であた。これに対し、重合時に揺動を与
えなかったもの(比較例1〜6)は、光学顕微鏡下の観
察の結果、その表面の一部もしくは全面にわたって白濁
部のあることが判明した。As is clear from Table 1, all of the samples in which the graft polymerization was shaken (Samples 1 to 6) had good surface conditions, with no clouding or the like. On the other hand, as a result of observation under an optical microscope, those that were not subjected to shaking during polymerization (Comparative Examples 1 to 6) were found to have cloudy parts over part or the entire surface.
以上の結果から、グラフト重合時に揺動を与えることに
より千ツマー溶液の濃度均一性が確保され、これが表面
グラフト状態を良好なものにする上で非常に効果の大き
いことが明かとなった。From the above results, it has become clear that the uniformity of the concentration of the Senzummer solution can be ensured by applying agitation during graft polymerization, and that this is very effective in improving the surface grafting state.
第1表
O表面状態良好(白濁無し)
X 表面状態不良(白濁有り)
[実施例2]
架橋剤であるN、N’−メチレンビスアクリルアミド2
゜5g、アクリルアミド10gを蒸留水に溶かして10
0m1とし、モノマー水溶液を調製した。Table 1 O: Good surface condition (no cloudiness)
Dissolve 5g of acrylamide and 10g of acrylamide in distilled water.
0 ml, and a monomer aqueous solution was prepared.
グラフト重合は次のようにして行なった。メチルメタク
リレート60wt%、 トリス(トリメチルシロキシ)
シリルプロピルメタクリレート35wt%、2−ヒドロ
キシエチルメタクリレート5wt%の共重合物よりなる
コンタクトレンズ基材を用意した。電極間距離3.5セ
ンチメートル、電極間電圧15キロボルト、周波数60
ヘルツのコロナ放電処理装置の電極間に厚み1.5ミリ
メートルのスペーサで作った空間にこのレンズ基材を設
置し、放電処理をおこなった。尚、片面ずつ、両面に4
0秒ずつ放電処理をした。次にこの放電処理したレンズ
基材を試験管に入れ、前記モノマー水溶液をレンズ基材
が十分浸かる量加えた。これを真空系に接続し、管内を
脱気し、そのまま真空封管を行った。この状態で試験管
を往復様どう機(EP−1、大洋サービスセンター株式
会社製)に挿入し揺動を与えながら80°Cの恒温下で
60分間基材表面へのグラフト重合処理を行った。重合
絆了イ釈 処理表面の白濁の有無を光学顕微鏡にて評価
した。尚、往復振どう機の揺動条件(揺動周期、振幅)
を第2表の如く設定し、6試料(試料1〜6)について
検討した。Graft polymerization was carried out as follows. Methyl methacrylate 60wt%, Tris (trimethylsiloxy)
A contact lens base material made of a copolymer of 35 wt% silylpropyl methacrylate and 5 wt% 2-hydroxyethyl methacrylate was prepared. Interelectrode distance 3.5 cm, interelectrode voltage 15 kilovolts, frequency 60
This lens base material was placed in a space created by a 1.5 mm thick spacer between the electrodes of a Hertz corona discharge treatment device, and discharge treatment was performed. In addition, 4 on each side, 4 on both sides.
Discharge treatment was performed for 0 seconds each. Next, this discharge-treated lens base material was placed in a test tube, and the monomer aqueous solution was added in an amount sufficient to soak the lens base material. This was connected to a vacuum system, the inside of the tube was degassed, and the tube was then vacuum sealed. In this state, the test tube was inserted into a reciprocating machine (EP-1, manufactured by Taiyo Service Center Co., Ltd.), and graft polymerization was performed on the substrate surface for 60 minutes at a constant temperature of 80°C while shaking. . The presence or absence of cloudiness on the treated surface was evaluated using an optical microscope. In addition, the swinging conditions of the reciprocating shaker (oscillation period, amplitude)
were set as shown in Table 2, and six samples (samples 1 to 6) were examined.
一方比較のため従来通り揺動を与えずに表面グラフト重
合処理を行ったものについても検討した(比較例1〜6
)。On the other hand, for comparison, we also investigated the surface graft polymerization treatment without shaking as usual (Comparative Examples 1 to 6).
).
第2表より明らかなように、グラフト重合時に揺動を与
えたもの(試料1〜6)については全て表面状態は良好
で白濁等は皆無であた。これに対し、重合時に揺動を与
えなかったもの(比較例1〜6)は、光学顕微鏡下の観
察の結果、その表面の一部もしくは全面にわたって白濁
部のあることが判明した。As is clear from Table 2, all of the samples subjected to shaking during graft polymerization (Samples 1 to 6) had good surface conditions, with no clouding or the like. On the other hand, as a result of observation under an optical microscope, those that were not subjected to shaking during polymerization (Comparative Examples 1 to 6) were found to have cloudy parts over part or the entire surface.
以上の結果から、グラフト重合時に揺動を与えることに
より千ツマー溶液の濃度均一性が確保され、これが表面
グラフト状態を良好なものにする上で非常に効果の大き
いことが明かとなった。From the above results, it has become clear that the uniformity of the concentration of the Senzummer solution can be ensured by applying agitation during graft polymerization, and that this is very effective in improving the surface grafting state.
第2表
O表面状態良好(白濁無し)
X 表面状態不良(白濁有り)
本発明の実施例をSi系PMMA製コンタクトレンズを
用いて説明してきたが、これに限られることなくポリエ
チレンフィルム、ポリプロピレン、ポリ塩化ビニル、ポ
リ塩化ビニリデン、アセテート、ポリエステル、ポリビ
ニルアルコール、ポリスチレン、ポリカーボネート、そ
の他様々な高分子材料の表面処理に対しても同様な結果
が得られた。更に、上にあげた材料を使用した各種包装
材、農業用保水材、または人工臓器などの医療用製品に
も応用が可能である。Table 2 O Good surface condition (no clouding) Similar results were obtained for surface treatments of polyvinyl chloride, polyvinylidene chloride, acetate, polyester, polyvinyl alcohol, polystyrene, polycarbonate, and various other polymeric materials. Furthermore, the above-mentioned materials can be applied to various packaging materials, agricultural water retaining materials, and medical products such as artificial organs.
[発明の効果]
以上述べたように、本発明によれば、グラフト重合時に
揺動を与えることにより千ツマー溶液の濃度均一性が確
保されるので、表面グラフト状態を良好なものにする上
で非常に効果の大きいことが明かとなった。[Effects of the Invention] As described above, according to the present invention, the uniformity of the concentration of the Senzummer solution is ensured by applying shaking during graft polymerization, which is effective in improving the surface grafting state. It turned out to be very effective.
以 上 出願人 セイコーエプソン株式会社that's all Applicant: Seiko Epson Corporation
Claims (1)
タクリレート( ▲数式、化学式、表等があります▼ 式中XおよびYはC_1〜C_5のアルキル基およびZ
基からなる群から選ばれ、Zは構造式 ▲数式、化学式、表等があります▼ をもつ基であり、AはC_1〜C_5のアルキル基を示
す。k、l、m、nは0、又は正の整数を示す。)との
共重合物であるメタクリル酸のエステル化合物のポリマ
ーを原材料としたコンタクトレンズ基材に関し、(a)
その表面を常圧あるいは減圧下で放電処理する工程と、
(b)前記基材をアクリルアミドを主成分とするモノマ
ー溶液に浸漬する工程と、(c)前記基材表面にアクリ
ルアミドをグラフト重合する工程とから成るコンタクト
レンズの製造方法において、前記(c)工程中の重合処
理を揺動を与えながら行うことを特徴とするコンタクト
レンズの製造方法。[Claims] At least alkyl methacrylate, siloxanyl methacrylate (▲There are mathematical formulas, chemical formulas, tables, etc.▼ In the formula, X and Y are C_1 to C_5 alkyl groups and Z
is selected from the group consisting of groups, Z is a group having the structural formula ▲ Numerical formula, chemical formula, table, etc. ▼, and A represents an alkyl group of C_1 to C_5. k, l, m, and n represent 0 or a positive integer. (a)
A process of discharging the surface under normal pressure or reduced pressure,
(b) immersing the base material in a monomer solution containing acrylamide as a main component; and (c) graft polymerizing acrylamide onto the surface of the base material. A method for manufacturing a contact lens, characterized in that the polymerization process inside the contact lens is performed while shaking the lens.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2309319A JP3013435B2 (en) | 1990-11-15 | 1990-11-15 | Method of manufacturing contact lenses |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2309319A JP3013435B2 (en) | 1990-11-15 | 1990-11-15 | Method of manufacturing contact lenses |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH04180013A true JPH04180013A (en) | 1992-06-26 |
JP3013435B2 JP3013435B2 (en) | 2000-02-28 |
Family
ID=17991587
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2309319A Expired - Lifetime JP3013435B2 (en) | 1990-11-15 | 1990-11-15 | Method of manufacturing contact lenses |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP3013435B2 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5391589A (en) * | 1991-12-10 | 1995-02-21 | Seiko Epson Corporation | Contact lens and method of producing a contact lens |
-
1990
- 1990-11-15 JP JP2309319A patent/JP3013435B2/en not_active Expired - Lifetime
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5391589A (en) * | 1991-12-10 | 1995-02-21 | Seiko Epson Corporation | Contact lens and method of producing a contact lens |
Also Published As
Publication number | Publication date |
---|---|
JP3013435B2 (en) | 2000-02-28 |
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