JPH03217816A - Production of contact lens - Google Patents
Production of contact lensInfo
- Publication number
- JPH03217816A JPH03217816A JP1411190A JP1411190A JPH03217816A JP H03217816 A JPH03217816 A JP H03217816A JP 1411190 A JP1411190 A JP 1411190A JP 1411190 A JP1411190 A JP 1411190A JP H03217816 A JPH03217816 A JP H03217816A
- Authority
- JP
- Japan
- Prior art keywords
- contact lens
- lens
- formula
- group
- polymerization
- 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.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 238000006116 polymerization reaction Methods 0.000 claims description 18
- 239000000463 material Substances 0.000 claims description 17
- -1 alkyl methacrylate Chemical compound 0.000 claims description 10
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- 238000007599 discharging Methods 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 150000002978 peroxides Chemical class 0.000 description 6
- 208000028659 discharge Diseases 0.000 description 5
- 238000012986 modification Methods 0.000 description 5
- 230000004048 modification Effects 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 239000007983 Tris buffer Substances 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 229920000578 graft copolymer Polymers 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 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
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000004087 cornea Anatomy 0.000 description 1
- 238000003851 corona treatment Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010559 graft polymerization reaction Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000002655 kraft paper Substances 0.000 description 1
- 229940127554 medical product Drugs 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
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001155 polypropylene 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
- 239000000047 product Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Macromonomer-Based Addition Polymer (AREA)
- Eyeglasses (AREA)
Abstract
(57)【要約】本公報は電子出願前の出願データであるた
め要約のデータは記録されません。(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明はコンタクトレンズに関し、特に濡れ性と装用感
に優れるハードコンタクトレンズに関する。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to contact lenses, and particularly to hard contact lenses that have excellent wettability and wear comfort.
[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、いわゆる
装用感を向上させる手段としては、コンタクトレンズ表
面に親水性モノマーをグラフト重合することにより濡れ
性を向上させ、角膜とレンズ表面のなじみを良くする方
法がある。重合に際しては、放電処理によりレンズ表面
に導入した過酸化物の一〇一〇一結合が切断するエネル
ギーを与える温度が必要である。従来、重合温度の設定
に間しては、開始種である過酸化物を分解するに足る温
度を供給しさえすれば良いとされていた。[Prior Art] As a means of reducing the foreign body sensation when wearing contact lenses and improving the so-called wearing comfort, it is possible to improve the wettability by graft polymerizing hydrophilic monomers on the contact lens surface, thereby creating a bond between the cornea and the lens surface. There are ways to improve familiarity. During polymerization, a temperature is required that provides energy to break the 10101 bonds of the peroxide introduced onto the lens surface through discharge treatment. Conventionally, when setting the polymerization temperature, it has been thought that it is sufficient to supply a temperature sufficient to decompose the peroxide, which is the starting species.
[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、重合温度が高すぎるとコ
スト高になるばかりか、レンズ材が変形および変質を起
こし表面改質としてはふさわしくない。また、重合温度
が低いとモノマーが3次元架橋構造を成し、水に不溶な
グラフトボリマーを形成することがある。この架橋クラ
フトボリマは突起物となってレンズ表面を侵し、濡れ性
を大幅に低下させるという欠点を有していた。そこで本
発明はこのような問題点を解決するもので、その目的と
するところは、レンズ表面に導入した過酸化物が分解す
るために必要最低限な温度を供給しながらも、レンズ材
が変形および変質することのないように温度を抑え、し
かもモノマーの3次元架橋を抑制するに足る高温である
ような最適重合温度を設定することにより,グラフト重
合を確実なもの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。[Problems to be Solved by the Invention] However, in the above-mentioned prior art, if the polymerization temperature is too high, not only will the cost increase, but the lens material will be deformed and altered, making it unsuitable for surface modification. Furthermore, if the polymerization temperature is low, the monomers may form a three-dimensional crosslinked structure, forming a graft polymer that is insoluble in water. This cross-linked kraft volima has the disadvantage that it forms protrusions that corrode the lens surface, significantly reducing wettability. The present invention is intended to solve these problems, and its purpose is to supply the minimum temperature necessary for the peroxide introduced to the lens surface to decompose, while also preventing the lens material from deforming. A contact lens manufacturing method that ensures graft polymerization by setting an optimal polymerization temperature that is high enough to suppress three-dimensional crosslinking of monomers and suppress the temperature to prevent deterioration. Our goal is to provide the following.
[課題を解決するための千段1
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、(1)少なくとも、アルキルメタクリレー
トとシロキサニルメタクリレート(式中XおよびYはC
1〜C5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Δ
のアルキル基を示す.m.nは0又は正の整数を示す。[1,000 Steps to Solve the Problems In order to solve the above problems, the method for manufacturing a contact lens of the present invention comprises (1) at least an alkyl methacrylate and a siloxanyl methacrylate (wherein X and Y are C
Z represents an alkyl group of the structural formula Δ. m. n represents 0 or a positive integer.
))
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おいて、
その表面を常圧あるいは減圧下で放電処理する工程と、
(2)レンズ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(2)工程の重合温度を60゜C〜90℃、望まし
くは80°C近傍に設定することにより成されることを
特徴とする。)) In contact lens base materials made from polymers of ester compounds of methacrylic acid, which are copolymers with
A process of discharging the surface under normal pressure or reduced pressure,
(2) A contact lens manufacturing method comprising the step of graft polymerizing acrylamide onto the lens surface,
It is characterized in that the polymerization temperature in step (2) is set at 60°C to 90°C, preferably around 80°C.
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。Typical ester compounds of methacrylic acid include the following.
ペンタメチルジシ口〜サニルメチルメタクIルートCH
3 CH3 0 CH311111
CH3−Si−0−Si−CH2−0−C−C=CH2
CH3 CH3
トリス(トリメチルシロキシ)−r−メタクリルオキシ
ブ口ピルシランCH.
CHa−Si−CH3
CH.0 0CH3I
I IllCH3−S
i−0−Si−CH.CH2CH2−0−C−C=CH
.曙
CH.O
CHz−Si−CHi
CHI
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
1ルートIll
CH3 CH. CH.
[イ乍 用1
コンタクトレンズの成形体を処理することにより成形体
の表面にラジカルが発生する。この成形体を酸素雰囲気
中にさらすと一〇−0−H等の過酸化物ができる。更に
これを親水性モノマー瀉液中に浸漬し、温度を上げると
過酸化物が分解して開始種となって重合が始まり、親水
性モノマーがグラフトすることになる。Pentamethylmethac I Route CH
3 CH3 0 CH311111 CH3-Si-0-Si-CH2-0-C-C=CH2
CH3 CH3 Tris(trimethylsiloxy)-r-methacryloxybutyrsilane CH. CHa-Si-CH3 CH. 0 0CH3I
I IllCH3-S
i-0-Si-CH. CH2CH2-0-C-C=CH
.. Akebono CH. O CHz-Si-CHi CHI Isobutylhexamethyltrisiloxanyl methyl methacrylate 1 route Ill CH3 CH. CH. [Use 1] Radicals are generated on the surface of the contact lens molded product by processing it. When this compact is exposed to an oxygen atmosphere, peroxides such as 10-0-H are produced. Furthermore, when this is immersed in a hydrophilic monomer filtrate and the temperature is raised, the peroxide decomposes and becomes an initiating species, starting polymerization and grafting the hydrophilic monomer.
以下、実施例により本発明の詳細を示す。Hereinafter, the details of the present invention will be shown by examples.
[実施例l]
メチルメタクリレート60wt%、トリス(トリメチル
シロキシ)シリルブ口ビルメタクリレト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センチメートル、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出でグロー放電処理をした。[Example 1] Methyl methacrylate 60 wt%, tris(trimethylsiloxy)silylbuvir methacrylate 35 wt%, 2
- A contact lens base material made of a copolymer of 5 wt % of hydroxyethyl methacrylate was prepared. Discharge device (
The lens base material was placed with a distance of 6 cm between the electrodes, an inter-electrode voltage of 270 volts, and a frequency of 60 Hz), and glow discharge treatment was performed in an argon atmosphere of 0.04 Torr.
放電処理したレンズ基材を空気中にだしたのち、レンズ
基材を試験管に入れそこへ10wt%アクリルアミド水
溶液を加え窒素ガス置換後、減圧封管した。試験管を6
0゜Cにて20分間恒諷槽中に置き、レンズ基材表面に
アクリルアミドをグラフト重合した。重合後,レンズを
70゜Cの熱純水中に浸漬し、一晩中純水を撹拌するこ
とによって副生ホモポリマーを除去した。重合温度を変
えて同様な操作を行い合計13個のサンプルを作製した
(第1表)。併せてレンズ表面の水に対する接触角を液
滴法にて測定した。これらの結果を第1表に掲げる。After the discharge-treated lens base material was exposed to the air, the lens base material was placed in a test tube, a 10 wt % acrylamide aqueous solution was added thereto, the tube was replaced with nitrogen gas, and the tube was sealed under reduced pressure. 6 test tubes
The lens was placed in a thermostatic bath at 0°C for 20 minutes to graft-polymerize acrylamide onto the surface of the lens base material. After polymerization, the lens was immersed in hot pure water at 70°C, and the by-product homopolymer was removed by stirring the pure water overnight. A total of 13 samples were prepared by performing the same operation while changing the polymerization temperature (Table 1). In addition, the contact angle of the lens surface with water was measured using a droplet method. These results are listed in Table 1.
レンズ基材変形
(実施例21
メチルメタクリレート60wt%、トリス(トノメチル
シロキシ)シリルブロビルメタクリレト35wt%、2
−ヒドロキシエチルメタクリレート5 w t%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14 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。面、片面
ずつ、両面に処理をした。次にこの放電処理したレンズ
基材を試験管に入れ、そこへ10wt%アクリルアミド
水溶液を加え窒素ガス置換後、減圧封管した。試験管を
60℃の恒温槽中に20分間置き、レンズ基材表面にア
クリルアミドをグラフト重合した。Lens base material modification (Example 21 60 wt% methyl methacrylate, 35 wt% tris(tonomethylsiloxy)silylbrobyl methacrylate, 2
A contact lens base material made of a copolymer of 5 wt% -hydroxyethyl methacrylate was prepared. This lens base material was placed in a space created by a 14.5 mm thick spacer between the electrodes of a corona discharge treatment device with an interelectrode distance of 3.5 cm, an interelectrode voltage of 15 kilovolts, and a frequency of 60 Hz, and the discharge treatment was performed. Ta. I treated both sides, one side at a time. Next, this discharge-treated lens base material was placed in a test tube, a 10 wt % acrylamide aqueous solution was added thereto, the tube was replaced with nitrogen gas, and the tube was sealed under reduced pressure. The test tube was placed in a constant temperature bath at 60° C. for 20 minutes to graft-polymerize acrylamide onto the surface of the lens base material.
重合後、レンズを70゜Cの熱純水中に浸漬し、一晩中
純水を撹拌することによって副生ホモボリマーを除去し
た。重合温度を変えて同様な操作を行い合計13個のサ
ンプルを作製した(第2表)。併せてレンズ表面の水に
対する接触角を液滴法にて測定した。これらの結果を第
2表に掲げる。After polymerization, the lens was immersed in hot pure water at 70°C, and the by-product homopolymer was removed by stirring the pure water overnight. A total of 13 samples were prepared by performing the same operation while changing the polymerization temperature (Table 2). In addition, the contact angle of the lens surface with water was measured using a droplet method. These results are listed in Table 2.
第2表
重合時間20分
ー・レンズ基材変形
第1表および第2表より明かな如く、試料1、2、すな
わち重合温度45゜C以下のものは、過酸化物分解が起
きなかったために接触角は下がらなかった。試料3、4
、すなわち重合温度50℃および55゜Cのものは、3
次元架橋グラフトポリマ一が生成するため接触角は高か
った。60゜C以上のとき(試料5〜11)接触角は著
しく低下し、特に80゜C以上のもの(試料9〜11)
については最小値をとった。しかし、重合温度90℃を
越えるとレンズ材が変形したため、表面改質としてはふ
さわしくない。Table 2 Polymerization time 20 minutes - Lens base material deformation As is clear from Tables 1 and 2, samples 1 and 2, that is, polymerization temperatures of 45°C or lower, did not undergo peroxide decomposition. The contact angle did not decrease. Samples 3 and 4
, that is, for polymerization temperatures of 50°C and 55°C, 3
The contact angle was high due to the formation of a dimensional cross-linked graft polymer. At temperatures above 60°C (samples 5 to 11), the contact angle decreases significantly, especially at temperatures above 80°C (samples 9 to 11).
The minimum value was taken for . However, when the polymerization temperature exceeds 90° C., the lens material is deformed, making it unsuitable for surface modification.
以上実施例1および実施例2に示した通り、重合温度を
60゜C〜90゜C、望ましくは8 0 ’C近傍に設
定するのが適当であるといえる。As shown in Examples 1 and 2 above, it can be said that it is appropriate to set the polymerization temperature at 60°C to 90°C, preferably around 80°C.
本発明の実施例をSi系PMMA製コンタクトレンズと
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、ボリブロビレン、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、ポリカーポネート、
その他様々なプラスチックフィルムの表百処理に対して
も同様な結果が得られた。更に、上にあげた樹脂を使用
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。Although the embodiments of the present invention have been described using Si-based PMMA contact lenses, the present invention is not limited thereto, and is not limited to polyethylene film, polypropylene, polyvinyl chloride,
Polyvinylidene chloride, acetate, polyester, polyvinyl alcohol, polystyrene, polycarbonate,
Similar results were obtained for various other types of plastic films treated with Table 100. Furthermore, the above-mentioned resins 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、重合温度を60℃〜
90℃、望ましくは80゜C近傍に設定することによっ
て、その後の表面改質の効果を恒常的に高めることが可
能となった。これにより、表面改質状態の不良や、ばら
つきが皆無となり、従って大量処理化や、大幅なコスト
ダウンが可能であるなど、そのもたらされる効果は多大
である。[Effects of the Invention] As described above, according to the present invention, the polymerization temperature is set at 60°C to
By setting the temperature to 90°C, preferably around 80°C, it became possible to permanently enhance the effect of subsequent surface modification. As a result, there are no defects or variations in the surface modification state, and the effects are great, such as mass processing and significant cost reductions.
以上that's all
Claims (1)
ニルメタクリレート( ▲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。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おいて、
その表面を常圧あるいは減圧下で放電処理する工程と、
(2)レンズ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(2)工程の重合温度を60℃〜90℃、望ましく
は80℃近傍に設定することにより成されることを特徴
とするコンタクトレンズの製造方法。(1) At least alkyl methacrylate and siloxanyl methacrylate (▲Mathematical formula, chemical formula, table, etc.▼ (In the formula, X and Y are selected from the group consisting of C_1 to C_5 alkyl groups and Z group, and Z is the structural formula▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ A is a group with C_1 to C_5 alkyl groups. m and n are 0 or positive integers.)) In contact lens base materials made from polymers of ester compounds,
A process of discharging the surface under normal pressure or reduced pressure,
(2) A contact lens manufacturing method comprising the step of graft polymerizing acrylamide onto the lens surface,
A method for manufacturing a contact lens, characterized in that the polymerization temperature in step (2) is set at 60°C to 90°C, preferably around 80°C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1411190A JPH03217816A (en) | 1990-01-24 | 1990-01-24 | Production of contact lens |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1411190A JPH03217816A (en) | 1990-01-24 | 1990-01-24 | Production of contact lens |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH03217816A true JPH03217816A (en) | 1991-09-25 |
Family
ID=11852007
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1411190A Pending JPH03217816A (en) | 1990-01-24 | 1990-01-24 | Production of contact lens |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH03217816A (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
- 1990-01-24 JP JP1411190A patent/JPH03217816A/en active Pending
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 |
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