JPH0467011A - Production of contact lens - Google Patents

Production of contact lens

Info

Publication number
JPH0467011A
JPH0467011A JP17845090A JP17845090A JPH0467011A JP H0467011 A JPH0467011 A JP H0467011A JP 17845090 A JP17845090 A JP 17845090A JP 17845090 A JP17845090 A JP 17845090A JP H0467011 A JPH0467011 A JP H0467011A
Authority
JP
Japan
Prior art keywords
acrylamide
graft
base material
lens base
contact lens
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
Application number
JP17845090A
Other languages
Japanese (ja)
Inventor
Hiroshi Kiguchi
浩史 木口
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Seiko Epson Corp
Original Assignee
Seiko Epson Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Seiko Epson Corp filed Critical Seiko Epson Corp
Priority to JP17845090A priority Critical patent/JPH0467011A/en
Publication of JPH0467011A publication Critical patent/JPH0467011A/en
Pending legal-status Critical Current

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  • Eyeglasses (AREA)
  • Surface Treatment Of Optical Elements (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Macromonomer-Based Addition Polymer (AREA)

Abstract

PURPOSE:To improve the adhesive strength of the tight contact between a lens base material and a graft polymer by adding a crosslinking agent to an aq. acrylamide monomer soln. in the case of a graft polymn. of acrylamide on the lens surface. CONSTITUTION:This production process has a stage for subjecting the surface of the contact lens base material formed from the polymer of the ester compd. of methacrylic acid which is the copolymer of alkyl methacrylate and siloxanyl methacrylate to an electric discharge treatment under atm. pressure or reduced pressure and a stage for subjecting the length surface to the graft polymn. of the acrylamide. The crosslinking agent is added to the aq. acrylamide monomer soln. in the stage for subjecting the contact lens surface to the graft polymn. of the acrylamide which is a hydrophilic monomer. The polymer subjected to the graft treatment has a crosslinked structure by adding the N, N'-methylene bisacrylamide to the aq. acrylamide monomer soln. which is a polymn. system in such a manner. The strength of the tight contact with the lens base material is intensified and the wear resistance is improved.

Description

【発明の詳細な説明】 C産業上の利用分野コ 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 the Invention The present invention relates to contact lenses, and particularly to hard contact lenses that are excellent in 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モノマー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。従来、アクリルアミドモノ
マーのみをコンタクトレンズ基材と接触させてグラフト
重合を行なっていた。
[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 monomer, onto the surface of the contact lens. Conventionally, graft polymerization has been carried out by bringing only acrylamide monomer into contact with a contact lens base material.

[発明が解決しようとする課M] しかし、前述の従来技術では、グラフトポリマーとレン
ズ基材との密着強度が小さく、指などでこするとグラフ
トポリマーがはげ落ちてしまい、グラフト前の濡れ性に
戻ってしまうという欠点を有していた。そこで本発明は
この問題点を解決するもので、その目的とするところは
、レンズ基材とグラフトポリマーとの密着強度を向上さ
せた、耐摩耗性の高いコンタクトレンズの製造方法を提
供することにある。
[Problem M to be solved by the invention] However, in the above-mentioned conventional technology, the adhesion strength between the graft polymer and the lens base material is low, and the graft polymer peels off when rubbed with fingers, resulting in poor wettability before grafting. It had the disadvantage of returning. Therefore, the present invention is intended to solve this problem, and its purpose is to provide a method for manufacturing contact lenses with high wear resistance that improves the adhesion strength between the lens base material and the graft polymer. be.

[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、 (a)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 をもつ基であり、Aは01〜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 includes: (a) at least alkyl methacrylate and siloxanyl methacrylate in which X and Y are C;
selected from the group consisting of a 1-C5 alkyl group and a Z group, Z is a group having a structural formula, and A represents an 01-C5 alkyl group.

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、 (b)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、 (b)工
程中のアクリルアミドモノマー水溶液に架橋剤を添加す
ることを特徴とする。
m and n are 0. Or indicates a positive integer. (b) Graft polymerization of acrylamide onto the lens surface in a contact lens base material made from a polymer of an ester compound of methacrylic acid, which is a copolymer with A method for manufacturing a contact lens comprising the steps of (b) adding a crosslinking agent to the aqueous acrylamide monomer solution in step (b).

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 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 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 者 CH3−8i−CH3 CH3−8i−CH3 CH3 以下、実施例により本発明の詳細を示す。
Pentamethyldisiloxanyl methyl methacrylate Isobutyl hexamethyltrisiloxanyl methyl methacrylate Tris(trimethylsiloxy)-γ-methacryloxypropylsilane Show details.

[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を水に溶かして100m
1とし、モノマー水溶液を調製した。
[Example 1] Crosslinking agent N,N'-methylenebisacrylamide 2
.. Dissolve 5g and 10g of acrylamide in water for 100m
1, and an aqueous monomer 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。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、0.041−−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、試験管に入れ
、架橋剤添加アクリルアミドモノマー水溶液を加え窒素
ガス置換後、減圧封管した。試験管を80°Cの恒温槽
中に60分置き、レンズ基材表面にアクリルアミドをグ
ラフト重合した(試料N011〜6)。また、従来法と
の比較のため、架橋剤未添加の10wt%アクリルアミ
ドモノマー水溶液を用いた試料を作製した。 (比較例
1〜6)この時の重合条件は、架橋剤添加の試料と全く
同様な操作を施した。併せて、処理後のレンズを、洗剤
をまぶした掌で1000往復こすり洗いをし、耐摩耗性
試験を行なった。グラフトポリマーの剥離評価は、こす
り前とこすり後のレンズ表面の接触角の変化で検討した
。接触角の測定は液適法にて行い、溶媒は水を使用した
。これらの結果を第1表に掲げる。
Graft polymerization was carried out as follows. A contact lens base material made of a copolymer of 60 wt% methyl methacrylate, 35 wt% tris(trimethylsiloxy)silylpropyl methacrylate, and 5 wt% 2-hydroxyethyl methacrylate was prepared. The lens base material was placed in a discharge device (electrode spacing 6 cm, interelectrode voltage 270 volts, frequency 60 hertz), and glow discharge treatment was performed for 5 seconds in an argon atmosphere of 0.041 mm. After exposing the discharge-treated lens base material to the air, it was placed in a test tube, a crosslinking agent-added acrylamide monomer aqueous solution was added, 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 80° C. for 60 minutes, and acrylamide was graft-polymerized on the surface of the lens base material (Samples Nos. 011 to 6). In addition, for comparison with the conventional method, a sample was prepared using a 10 wt % acrylamide monomer aqueous solution to which no crosslinking agent was added. (Comparative Examples 1 to 6) The polymerization conditions at this time were exactly the same as those for the samples with the addition of a crosslinking agent. In addition, the treated lenses were rubbed 1,000 times with the palm of the hand sprinkled with detergent to perform an abrasion resistance test. Graft polymer peeling was evaluated by examining the change in contact angle between the lens surface before and after rubbing. The contact angle was measured by the dripping method, and water was used as the solvent. These results are listed in Table 1.

第1表 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ワレート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。電極間路
93. 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40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、そこへ実施例1に用
いたものと同様の架橋剤添加アクリルアミドモノマー水
溶液を加え窒素ガス置換後、減圧封管した。試験管を8
0°Cの恒温槽中に60分置き、レンズ基材表面にアク
リルアミドをグラフト重合した(試料NO,1〜6)。
Table 1 Methyl methacrylate 60 wt%, tris(trimethylsiloxy)silylpropyl methacrylate 35 wt%,
A contact lens base material made of a copolymer of 5 wt% 2-hydroxyethyl methacryate was prepared. Interelectrode path 93. This lens base material was placed in a space created by a 1.5 mm thick spacer between the electrodes of a corona discharge treatment device with a diameter of 5 cm, an interelectrode voltage of 15 kilovolts, and a frequency of 60 Hz, and discharge treatment was performed. Incidentally, discharge treatment was applied to one side and both sides for 40 seconds each. Next, this discharge-treated lens base material was placed in a test tube, and the same crosslinking agent-added acrylamide monomer aqueous solution as used in Example 1 was added thereto, and the tube was sealed under reduced pressure after purging with nitrogen gas. 8 test tubes
The lenses were placed in a constant temperature bath at 0° C. for 60 minutes to graft-polymerize acrylamide onto the surface of the lens base material (Samples Nos. 1 to 6).

また、従来法との比較のため、架橋剤未添加の10wt
%アクリルアミド水溶液を用いた試料を作製した。
In addition, for comparison with the conventional method, 10 wt without crosslinking agent was added.
% acrylamide aqueous solution was prepared.

(比較例1〜6)この時の重合条件は架橋剤添加の試料
と全く同様な操作を施した。併せて、処理後のレンズを
、洗剤をまぶした掌で1000往復こすり洗いをし、耐
摩耗性試験を行なった。グラフトポリマーの剥離評価は
、こすり前とこすり後のレンズ表面の接触角の変化で検
討した。接触角の測定は液適法にて行い、溶媒は水を使
用した。
(Comparative Examples 1 to 6) The polymerization conditions at this time were exactly the same as those for the samples in which a crosslinking agent was added. In addition, the treated lenses were rubbed 1,000 times with the palm of the hand sprinkled with detergent to perform an abrasion resistance test. Graft polymer peeling was evaluated by examining the change in contact angle between the lens surface before and after rubbing. The contact angle was measured by the dripping method, and water was used as the solvent.

これらの結果を第2表に掲げる。These results are listed in Table 2.

第2表 第1fiEよひ第2坂より明かなように、こすり後の接
触角の上昇は、架橋剤を添加することにより大幅に抑制
され、レンズ表面の水濡れ性は保持された。すなわち、
アクリルアミドポリマーはN、N−メチレンビスアクリ
ルアミド架橋することにより、レンズ基材とグラフトポ
リマーの密着強度が大きくなり、グラフトレンズ表面の
耐摩耗性を向上させることができた。
As is clear from the second slope of Table 2, the increase in the contact angle after rubbing was significantly suppressed by adding the crosslinking agent, and the water wettability of the lens surface was maintained. That is,
By crosslinking the acrylamide polymer with N,N-methylenebisacrylamide, the adhesion strength between the lens base material and the graft polymer was increased, and the abrasion resistance of the graft lens surface was able to be improved.

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、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、
その他種々なプラスチックフィルムの表面処理に対して
も同様な結果が得られた。更に、上にあげた樹朋を使用
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 explained using Si-based PMMA contact lenses, the present invention is not limited thereto, and is not limited to polyethylene films, polypropylene, polyvinyl chloride,
Polyvinylidene chloride, acetate, polyester, polyvinyl alcohol, polystyrene, polycarbonate,
Similar results were obtained for surface treatments of various other plastic films. Furthermore, the above-mentioned trees can be used in various packaging materials, agricultural water retaining materials, and medical products such as artificial organs.

また、架橋剤としてグリセリンジアクリレート、トリメ
チロールプロパントリアクリレートなどのアクリレート
系、およびエチレングリコールジメタクリレート、ジエ
チレングイコールジメタクリレート、 トリエチレング
リコールジメタクリレート、1.3−ブタンジオールジ
メタクリレートなどのメタクリレート系を用いても同様
な結果が得られた。
In addition, as a crosslinking agent, acrylates such as glycerin diacrylate and trimethylolpropane triacrylate, and methacrylates such as ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, and 1,3-butanediol dimethacrylate are used. Similar results were obtained using

[発明の効果コ 以上述べたように、発明によれば、重合系たるアクリル
アミドモノマー水溶液にN、N’−メチレンビスアクリ
ルアミドを添加することにより、グラフト処理したポリ
マーは架橋構造をとり、レンズ基材との密着強度が強ま
って耐摩耗性が飛躍的に向上した。これは、コンタクト
レンズの水濡れ性を長期にわたって保持できるという効
果を有する。
[Effects of the Invention] As described above, according to the invention, by adding N,N'-methylenebisacrylamide to the acrylamide monomer aqueous solution that is the polymerization system, the grafted polymer takes on a crosslinked structure and forms a lens base material. The adhesion strength has been strengthened and wear resistance has been dramatically improved. This has the effect that the water wettability of the contact lens can be maintained for a long period of time.

従って、本発明は装用感に優れるコンタクトレンズの製
造に関し、たいへん有効な方法であるといえる。
Therefore, the present invention can be said to be a very effective method for producing contact lenses that are comfortable to wear.

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)

【特許請求の範囲】 (a)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( ▲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、(b)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、(b)工程中
のアクリルアミドモノマー水溶液に架橋剤を添加するこ
とを特徴とするコンタクトレンズの製造方法。
[Claims] (a) At least alkyl methacrylate and 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. m and n represent 0 or a positive integer. (b) Graft polymerization of acrylamide onto the lens surface in a contact lens base material made from a polymer of a methacrylic acid ester compound, which is a copolymer with A method for producing a contact lens comprising the step of (b) adding a crosslinking agent to the aqueous acrylamide monomer solution in step (b).
JP17845090A 1990-07-05 1990-07-05 Production of contact lens Pending JPH0467011A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP17845090A JPH0467011A (en) 1990-07-05 1990-07-05 Production of contact lens

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP17845090A JPH0467011A (en) 1990-07-05 1990-07-05 Production of contact lens

Publications (1)

Publication Number Publication Date
JPH0467011A true JPH0467011A (en) 1992-03-03

Family

ID=16048734

Family Applications (1)

Application Number Title Priority Date Filing Date
JP17845090A Pending JPH0467011A (en) 1990-07-05 1990-07-05 Production of contact lens

Country Status (1)

Country Link
JP (1) JPH0467011A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
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

Cited By (1)

* Cited by examiner, † Cited by third party
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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