JPH0940720A - Soft contact lens - Google Patents
Soft contact lensInfo
- Publication number
- JPH0940720A JPH0940720A JP20851295A JP20851295A JPH0940720A JP H0940720 A JPH0940720 A JP H0940720A JP 20851295 A JP20851295 A JP 20851295A JP 20851295 A JP20851295 A JP 20851295A JP H0940720 A JPH0940720 A JP H0940720A
- Authority
- JP
- Japan
- Prior art keywords
- lens
- copolymer
- contact lens
- polyvinyl alcohol
- vinyl acetate
- 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
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Eyeglasses (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、ＰＶＡソフトコン
タクトレンズに関する。更に詳しく述べるなら、含水率
３０〜８０％の架橋ポリビニルアルコ−ルソフトコンタ
クトレンズに関する。TECHNICAL FIELD The present invention relates to a PVA soft contact lens. More specifically, it relates to a crosslinked polyvinyl alcohol soft contact lens having a water content of 30 to 80%.
【０００２】[0002]
【従来の技術】一般にポリビニルアルコ−ルは、ポリ酢
酸ビニルの加水分解によって得ることが出来るが、ポリ
ビニルアルコ−ルを架橋するのは簡単なことではない。
従来、ポリビニルアルコ−ルを架橋する方法は、ポリ酢
酸ビニルの加水分解によって得られたポリビニルアルコ
−ルをアルデヒド等により後から架橋することが行われ
てきた。しかし、この方法では、架橋の程度を精密にコ
ントロ−ルすることは、容易でない。又、ポリビニルア
ルコ−ル自体をレンズ状に成形することも難しく、従っ
て架橋ポリビニルアルコ−ル製の含水ソフトコンタクト
レンズは未だ実用化されていない。この意味から含水率
の高い架橋ポリビニルアルコ−ルソフトコンタクトレン
ズの容易な製造方法の開発の出現が強く望まれている。2. Description of the Related Art Generally, polyvinyl alcohol can be obtained by hydrolysis of polyvinyl acetate, but it is not easy to crosslink polyvinyl alcohol.
Conventionally, the method for crosslinking polyvinyl alcohol has been to cross-link polyvinyl alcohol obtained by hydrolysis of polyvinyl acetate with an aldehyde or the like afterwards. However, with this method, it is not easy to precisely control the degree of crosslinking. It is also difficult to mold the polyvinyl alcohol itself into a lens shape, and therefore, a hydrous soft contact lens made of crosslinked polyvinyl alcohol has not been put into practical use. From this point of view, it is strongly desired to develop a method for easily producing a crosslinked polyvinyl alcohol soft contact lens having a high water content.
【０００３】[0003]
【発明が解決しようとする課題】本発明は、以上の要請
に応え、新規な含水率の高い架橋ポリビニルアルコ−ル
製ソフトコンタクトレンズを提供することを目的とす
る。具体的には、含水率３０〜８０％の架橋ポリビニル
アルコ−ルソフトコンタクトレンズを目的とする。SUMMARY OF THE INVENTION It is an object of the present invention to provide a new soft contact lens made of crosslinked polyvinyl alcohol having a high water content in response to the above demands. Specifically, the object is a crosslinked polyvinyl alcohol soft contact lens having a water content of 30 to 80%.
【０００４】[0004]
【課題を解決するための手段】本発明の架橋ポリビニル
アルコ−ルソフトコンタクトレンズは、酢酸ビニルとジ
アリリデンペンタエリスリットからなる共重合体をレン
ズ状に研削、研磨し、更に加水分解することによって得
られる有用な架橋ポリビニルアルコ−ル製ソフトコンタ
クトレンズである。The cross-linked polyvinyl alcohol soft contact lens of the present invention is obtained by grinding and polishing a copolymer of vinyl acetate and diarylidene pentaerythrite into a lens shape and further hydrolyzing it. It is a useful soft contact lens made of crosslinked polyvinyl alcohol obtained by.
【０００５】本発明の新規なポリビニルアルコ−ル製ソ
フトコンタクトレンズは、特定のモノマ−のラジカル共
重合によって得られる。本発明において用いられるモノ
マ−は、酢酸ビニルと下記化２〔構造式（１）〕で示さ
れるジアリリデンペンタエリスリットであり、この２種
類モノマ−はラジカル共重合性に富む。The novel polyvinyl alcohol soft contact lens of the present invention is obtained by radical copolymerization of a specific monomer. The monomer used in the present invention is vinyl acetate and diarylidene pentaerythritol represented by the following Chemical Formula 2 [Structural Formula (1)], and these two kinds of monomers are excellent in radical copolymerizability.
【０００６】[0006]
【化２】 Embedded image
【０００７】本発明では、この共重合体を９０〜９９．
９５重量％の酢酸ビニルと０．０５〜１０％のジアリリ
デンペンタエリスリットを通常のラジカル重合開始剤を
用いて、塊状重合を行うことにより得られる。本発明に
おいてモノマ−の組成が９０〜９９．９５重量％の酢酸
ビニルと０．０５〜１０重量％のジアリリデンペンタエ
リスリットの範囲で使用される理由は、架橋成分として
のジアリリデンペンタエリスリットが０．０５重量％を
下回ると加水分解後のポリビニルアルコ−ルの架橋が不
十分で、ソフトコンタクトレンズに適した強度のある含
水ゲルにならないためである。又、ジアリリデンペンタ
エリスリットが１０重量％を超えると架橋が高すぎ、充
分柔なんなゲルにならず、また本発明の高い含水率を持
つことが出来ないためである。In the present invention, this copolymer is used in the range of 90-99.
It is obtained by bulk polymerization of 95% by weight of vinyl acetate and 0.05 to 10% of diarylidene pentaerythritol using a usual radical polymerization initiator. In the present invention, the reason why the composition of the monomer is 90 to 99.95% by weight of vinyl acetate and 0.05 to 10% by weight of diarylidene pentaerythritol is used as a crosslinking component. This is because if the Erythrite is less than 0.05% by weight, the polyvinyl alcohol after hydrolysis is insufficiently crosslinked and a hydrogel having strength suitable for a soft contact lens cannot be obtained. On the other hand, if the amount of diarylidene pentaerythrite exceeds 10% by weight, the crosslinking will be too high to form a sufficiently soft gel and the high water content of the present invention cannot be achieved.
【０００８】塊状重合は、本発明では、ポリエチレンや
ポリプロピレン、ポリテトラフロロエチレン等のプラス
チック製の試験管などの容器中に、９０〜９９．９５重
量％の酢酸ビニルと０．０５〜１０％のジアリリデンペ
ンタエリスリットと適量のラジカル重合開始剤の混合物
をいれ、加温下に重合を行う。重合は、ラジカル重合開
始剤の種類によって異なるが、通常室温から１００℃の
間で行われ、透明な成形体が得られる。この様にして得
られた成形体は、研削、研磨されレンズ状に成形される
が、９０〜９９．９５重量％の酢酸ビニルと０．０５〜
１０％のジアリリデンペンタエリスリットの共重合体
は、室温では、柔なんであり、通常これを研削研磨して
レンズ状に成形することは困難である。この為、本発明
ではこの共重合体を冷却下に成形する。一例を示すと通
常、先ず酢酸ビニルとジアリリデンペンタエリスリット
の共重合体を約−２０℃に冷却する。次にこの架橋共重
合体を冷水をかけながら研削、研磨を行いコンタクトレ
ンズ状に成形される。次に、レンズ状に成形された酢酸
ビニルとジアリリデンペンタエリスリットの共重合体は
加水分解され、ビニルアルコ−ル−ジアリリデンペンタ
エリスリット共重合体になる。In the present invention, the bulk polymerization is carried out in a container such as a test tube made of a plastic such as polyethylene, polypropylene or polytetrafluoroethylene by using 90 to 99.95% by weight of vinyl acetate and 0.05 to 10% of vinyl acetate. A mixture of diallylidene pentaerythritol and an appropriate amount of a radical polymerization initiator is added, and polymerization is carried out under heating. Although the polymerization depends on the type of radical polymerization initiator, it is usually carried out at room temperature to 100 ° C. to obtain a transparent molded product. The molded product thus obtained is ground and polished to be molded into a lens shape, and contains 90 to 99.95% by weight of vinyl acetate and 0.05 to 99% by weight.
A 10% copolymer of diarylidene pentaerythritol is soft at room temperature, and it is usually difficult to grind and polish it to form a lens. Therefore, in the present invention, this copolymer is molded under cooling. As an example, usually, a copolymer of vinyl acetate and diarylidene pentaerythritol is first cooled to about -20 ° C. Next, this crosslinked copolymer is ground and polished while being sprayed with cold water to form a contact lens. Next, the lens-shaped copolymer of vinyl acetate and diarylidene pentaerythritol is hydrolyzed into a vinyl alcohol-diallylidene pentaerythritol copolymer.
【０００９】加水分解方法は特に、限定は無いが、アル
カリ性の水溶液に共重合体をいれることにより行われ
る。例えば、酢酸ビニルとジアリリデンペンタエリスリ
ットの共重合体を予めメタノ−ルやエタノ−ル等の有機
溶媒で膨潤させておき、これを苛性ソーダ水溶液とメタ
ノ−ルやエタノ−ル等の有機溶媒との混合溶液中にい
れ、加温下に加水分解を行う。この際、鹸化の程度は、
特に、限定はないが本発明では、通常８０から１００％
の鹸化度のものがコンタクトレンズとして用いられる。
本発明では、この様に加水分解された架橋されたビニル
アルコ−ル−ジアリリデンペンタエリスリット共重合体
は多量の水で洗浄されコンタクトレンズとして供され
る。The hydrolysis method is not particularly limited, but it is carried out by putting the copolymer in an alkaline aqueous solution. For example, a copolymer of vinyl acetate and diarylidene pentaerythritol is swollen in advance with an organic solvent such as methanol or ethanol, and this is swelled with an aqueous solution of caustic soda and an organic solvent such as methanol or ethanol. It is put in a mixed solution with and hydrolyzed under heating. At this time, the degree of saponification is
In the present invention, although not particularly limited, it is usually 80 to 100%.
A contact lens having a saponification degree of is used as a contact lens.
In the present invention, the thus hydrolyzed and crosslinked vinyl alcohol-dialylidene pentaerythritol copolymer is washed with a large amount of water and used as a contact lens.
【００１０】通常、鹸化後の共重合体レンズの度数と鹸
化前の共重合体レンズの度数は異なる場合が多いので、
予めこの事を考慮して、鹸化前の酢酸ビニルとジアリリ
デンペンタエリスリットの共重合体の研削、研磨成形を
行う必要があることは、当然である。この様にして得ら
れた本発明になる架橋ポリビニルアルコ−ルコンタクト
レンズは、ポリビニルアルコ−ルと言う極めて単純な構
造を有しており、安全で含水率が３０〜８０％と含水ソ
フトコンタクトレンズとして適当であり、柔なんで、且
つ長期に亘っての安定性に優れた有用なソフトコンタク
トレンズを提供するものである。Usually, the power of the copolymer lens after saponification and the power of the copolymer lens before saponification are often different,
Considering this in advance, it is natural that it is necessary to grind and polish the copolymer of vinyl acetate and diarylidene pentaerythritol before saponification. The crosslinked polyvinyl alcohol contact lens of the present invention thus obtained has a very simple structure called polyvinyl alcohol, is safe, and has a water content of 30 to 80%, and a soft water contact lens. The present invention provides a useful soft contact lens which is suitable as, is soft, and has excellent stability over a long period of time.
【００１１】[0011]
実施例 （１） 蒸留、精製された酢酸ビニル ９８．５ 重量部 ジアリリデンペンタエリスリット １．５ 重量部 を混合し、これにラウリルパ−オキサイド０．５重量部
を添加混合してモノマ−溶液とした。これを直径１０ｍ
ｍのポリプロピレン製試験管にいれ、系内を窒素置換し
て上部を密閉した。これを４５℃のオ−ブン中にいれ、
１６時間保持した後、８０℃まで徐々に昇温することに
より重合を完結させた。この共重合体を−２０℃に冷却
した後、２℃の冷水を掛けながら研削、研磨を行いレン
ズ状に成形した。このレンズ状に成形された共重合体を
室温でメタノ−ル中にいれ膨潤させた。更に５ｇ／ｌ
（リットル）の濃度にＮａＯＨを溶解させたメタノ−ル
溶液中にいれ、５０℃で６時間加水分解を行った。レン
ズ成形体を取り出し、多量の水でよく水洗し、架橋ポリ
ビニルアルコ−ルコンタクトレンズを得た。このゲルは
透明でありかつ柔なんで二つに折曲げても破砕しない丈
夫なゲルであった。赤外分光より、酢酸ビニルのビニル
アルコ−ルへの鹸化は、約１００％進行していることを
確認した。この架橋ポリビニルアルコ−ルゲルの含水率
は、約３５％であった。含水率は、次式より求めた。 ここで Ｗh は水を飽和したゲルの重量 Ｗd は乾燥時のゲルの重量Example (1) Distilled and purified vinyl acetate 98.5 parts by weight Diarylidene pentaerythritol 1.5 parts by weight was mixed, and 0.5 parts by weight of lauryl peroxide was added and mixed therein to obtain a monomer solution. And This is 10m in diameter
It was put in a polypropylene test tube of m, the system was replaced with nitrogen, and the upper part was sealed. Place this in an oven at 45 ° C,
After holding for 16 hours, the temperature was gradually raised to 80 ° C. to complete the polymerization. This copolymer was cooled to −20 ° C., and then ground and polished while being chilled with 2 ° C. cold water to form a lens. The lens-shaped copolymer was allowed to swell in methanol at room temperature. 5g / l
It was placed in a methanol solution in which NaOH was dissolved at a concentration of (liter) and hydrolyzed at 50 ° C. for 6 hours. The lens molded body was taken out and washed thoroughly with a large amount of water to obtain a crosslinked polyvinyl alcohol contact lens. Since this gel was transparent and soft, it was a tough gel that would not break even when folded in two. From infrared spectroscopy, it was confirmed that the saponification of vinyl acetate into vinyl alcohol proceeded to about 100%. The water content of this crosslinked polyvinyl alcohol gel was about 35%. The water content was calculated from the following formula. Where W h is the weight of the gel saturated with water W d is the weight of the gel when dried
【００１２】実施例（２） 蒸留、精製された酢酸ビニル ９９．８ 重量部 ジアリリデンペンタエリスリット ０．２ 重量部 を混合し、これにラウリルパ−オキサイド０．５重量部
を添加混合してモノマ−溶液とした。実施例（１）と同
じ方法で重合を行い、更に、研削研磨してレンズ状成形
物をえた。更に、実施例（１）と同じ方法で加水分解を
行い架橋ポリビニルアルコ−ルゲルを得た。このゲルは
透明でありかつ柔なんで二つに折曲げても破砕しない丈
夫なゲルであった。赤外分光より、酢酸ビニルのビニル
アルコ−ルへの鹸化は、約１００％進行していることを
確認した。この架橋ポリビニルアルコ−ルゲルの含水率
は、約７２％であった。Example (2) Distilled and purified vinyl acetate 99.8 parts by weight Diarylidene pentaerythritol 0.2 parts by weight was mixed, and 0.5 parts by weight of lauryl peroxide was added and mixed. It was a monomer solution. Polymerization was carried out in the same manner as in Example (1), and then ground and polished to obtain a lens-shaped molded product. Further, hydrolysis was carried out in the same manner as in Example (1) to obtain a crosslinked polyvinyl alcohol gel. Since this gel was transparent and soft, it was a tough gel that would not break even when folded in two. From infrared spectroscopy, it was confirmed that the saponification of vinyl acetate into vinyl alcohol proceeded to about 100%. The water content of this crosslinked polyvinyl alcohol gel was about 72%.
【００１３】[0013]
【発明の効果】本発明のコンタクトレンズは、新規なポ
リビニルアルコ−ル製コンタクトレンズであって、含水
率が３０〜８０％に架橋され、柔なんで、且つ長期に亘
っての安定性に優れた有用なソフトコンタクトレンズを
提供するものである。Industrial Applicability The contact lens of the present invention is a novel polyvinyl alcohol contact lens having a water content of 30 to 80% crosslinked, is soft, and is excellent in stability over a long period of time. It is intended to provide a useful soft contact lens.
Claims (1)
０．０５〜１０重量％の下記化１〔構造式（１）〕で示
されるジアリリデンペンタエリスリットからなる共重合
体を冷却下、レンズ状に研削、研磨し、更に加水分解す
ることにより得られることを特徴とする含水率３０〜８
０％の架橋ポリビニルアルコ−ルソフトコンタクトレン
ズ。 【化１】 1. A copolymer comprising 90 to 99.95% by weight of vinyl acetate and 0.05 to 10% by weight of diarylidene pentaerythritol represented by the following chemical formula 1 [structural formula (1)]. A water content of 30 to 8, which is obtained by grinding, polishing, and further hydrolyzing under the shape of a lens.
0% cross-linked polyvinyl alcohol soft contact lens. Embedded image
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20851295A JP2990492B2 (en) | 1995-07-25 | 1995-07-25 | Soft contact lens |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20851295A JP2990492B2 (en) | 1995-07-25 | 1995-07-25 | Soft contact lens |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0940720A true JPH0940720A (en) | 1997-02-10 |
| JP2990492B2 JP2990492B2 (en) | 1999-12-13 |
Family
ID=16557398
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP20851295A Expired - Fee Related JP2990492B2 (en) | 1995-07-25 | 1995-07-25 | Soft contact lens |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2990492B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999006199A1 (en) * | 1997-07-31 | 1999-02-11 | Seed Co., Ltd. | Process for preparing polyvinyl alcohol contact lenses |
-
1995
- 1995-07-25 JP JP20851295A patent/JP2990492B2/en not_active Expired - Fee Related
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999006199A1 (en) * | 1997-07-31 | 1999-02-11 | Seed Co., Ltd. | Process for preparing polyvinyl alcohol contact lenses |
| AU739519B2 (en) * | 1997-07-31 | 2001-10-11 | Seed Co. Ltd | Process for preparing polyvinyl alcohol contact lenses |
| US6402995B1 (en) | 1997-07-31 | 2002-06-11 | Seed Co., Ltd. | Process for preparing polyvinyl alcohol contact lenses |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2990492B2 (en) | 1999-12-13 |
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