JP2881808B2 - contact lens - Google Patents
contact lensInfo
- Publication number
- JP2881808B2 JP2881808B2 JP10067289A JP10067289A JP2881808B2 JP 2881808 B2 JP2881808 B2 JP 2881808B2 JP 10067289 A JP10067289 A JP 10067289A JP 10067289 A JP10067289 A JP 10067289A JP 2881808 B2 JP2881808 B2 JP 2881808B2
- Authority
- JP
- Japan
- Prior art keywords
- contact lens
- monomer
- lens according
- methacrylate
- ester compound
- 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.)
- Expired - Fee Related
Links
- 239000000178 monomer Substances 0.000 claims description 18
- 238000009832 plasma treatment Methods 0.000 claims description 8
- -1 ester compound Chemical class 0.000 claims description 7
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 5
- 239000012298 atmosphere Substances 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 4
- 239000002202 Polyethylene glycol Substances 0.000 claims description 4
- 230000001588 bifunctional effect Effects 0.000 claims description 4
- 229920001223 polyethylene glycol Polymers 0.000 claims description 4
- 229920000642 polymer Polymers 0.000 claims description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 3
- 229920001577 copolymer Polymers 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 239000000758 substrate Substances 0.000 claims description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 2
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical group C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 claims description 2
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 claims description 2
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 claims description 2
- 229920002689 polyvinyl acetate Polymers 0.000 claims description 2
- 239000011118 polyvinyl acetate Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 1
- TURITJIWSQEMDB-UHFFFAOYSA-N 2-methyl-n-[(2-methylprop-2-enoylamino)methyl]prop-2-enamide Chemical compound CC(=C)C(=O)NCNC(=O)C(C)=C TURITJIWSQEMDB-UHFFFAOYSA-N 0.000 claims 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims 1
- 238000011282 treatment Methods 0.000 description 4
- 208000028659 discharge Diseases 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 2
- BESKSSIEODQWBP-UHFFFAOYSA-N 3-tris(trimethylsilyloxy)silylpropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC[Si](O[Si](C)(C)C)(O[Si](C)(C)C)O[Si](C)(C)C BESKSSIEODQWBP-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 238000003851 corona treatment Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229920001477 hydrophilic polymer Polymers 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Landscapes
- Eyeglasses (AREA)
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。Description: TECHNICAL FIELD The present invention relates to a contact lens, and more particularly to a hard contact lens excellent in wettability and wearing feeling.
プラズマ処理によるソフトコンタクトレンズの濡れ性
の改良は特許公報63−40293号等に述べられている。Improvement of wettability of soft contact lenses by plasma treatment is described in Japanese Patent Publication No. 63-40293.
また、ハードコンタクトレンズの表面をプラズマ処理
し表面に親水基をつくりだして濡れ性をもたせる方法も
提案されている。Also, a method has been proposed in which the surface of a hard contact lens is subjected to plasma treatment to create a hydrophilic group on the surface to impart wettability.
しかし、従来のプラズマ処理はシリコンラバー系のソ
フトコンタクトレンズを処理し表面の濡れ性を改良する
ものが多く、ハードコンタクトレンズを処理したものは
少ない。However, many conventional plasma treatments treat silicon rubber-based soft contact lenses to improve the wettability of the surface, and few treat hard contact lenses.
ハードコンタクトレンズを処理した例としては、表面
を単にプラズマ処理だけし、親水性をもたせたものがあ
る。しかし、この場合、親水性の基がすぐに樹脂中に隠
れてしまい親水性がなくなってしまう欠点があった。ま
た、親水性は改良されるものの、装用感の改良まではい
たらず、装用性の面でソフトコンタクトレンズにかなわ
ない欠点があった。As an example of treating a hard contact lens, there is one in which the surface is simply subjected to a plasma treatment to impart hydrophilicity. However, in this case, there is a disadvantage that the hydrophilic group is immediately hidden in the resin and the hydrophilicity is lost. Further, although the hydrophilicity is improved, the wearing feeling is not improved, and there is a drawback that the wearing property is inferior to that of the soft contact lens.
そこで本発明では、ハードコンタクトレンズ、特にメ
タクリル酸のエステル化合物の重合体を含有する基材よ
りなるコンタクトレンズをプラズマ処理した後、酸素雰
囲気にさらし、１官能性のモノマーと２官能性のモノマ
ーを含有する親水性モノマー溶液中で処理し、グラフト
化させることにより、コンタクトレンズに親水性をもた
せ、装用感を改良することを目的とするものである。Therefore, in the present invention, a hard contact lens, particularly a contact lens made of a base material containing a polymer of an ester compound of methacrylic acid, is subjected to plasma treatment, and then exposed to an oxygen atmosphere, and a monofunctional monomer and a bifunctional monomer are treated. An object of the present invention is to provide a contact lens with hydrophilicity and to improve a feeling of wearing by treating in a contained hydrophilic monomer solution and grafting.
本発明のコンタクトレンズは次の工程により表面処理
されることを特徴とする。The contact lens of the present invention is characterized by being subjected to a surface treatment by the following steps.
1.コンタクトレンズ成形体の表面をプラズマ処理する。1. Plasma treatment of the surface of the contact lens molded body.
2.プラズマ処理した成形体を酸素雰囲気にさらす。（空
気中でプラズマ処理した場合は、酸素雰囲気にさらさな
くてもよい場合がある） 3.処理した成形体を１官能性モノマーと２官能性モノマ
ーを含有する親水性モノマー溶液中に浸漬し、重合させ
る。2. Exposing the plasma-treated molded body to an oxygen atmosphere. (If plasma treatment is performed in air, it may not be necessary to expose to an oxygen atmosphere.) 3. Dip the treated molded body in a hydrophilic monomer solution containing a monofunctional monomer and a bifunctional monomer, Polymerize.
4.不要な重合物や、未反応物を洗い落とす。4. Wash off unnecessary polymer and unreacted material.
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
気にさらすと−Ｏ−Ｏ−Ｈ等の過酸化物ができる。By treating the molded body of the contact lens, radicals are generated on the surface of the molded body. When this molded body is exposed to an oxygen atmosphere, a peroxide such as —O—O—H is formed.
この成形体を親水性モノマー溶液中に浸漬し、温度を
あげることにより、過酸化物が分解し、開始剤となり、
重合が始まり、親水性のモノマーがグラフトすることに
なる。By immersing this molded body in a hydrophilic monomer solution and raising the temperature, the peroxide is decomposed and becomes an initiator,
Polymerization starts, and the hydrophilic monomer is grafted.
以下、実施例により本発明の詳細を示す。 Hereinafter, the present invention will be described in detail with reference to examples.
（実施例１） メチルメタクリレート 60重量パーセント、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
35重量パセント、２−ヒドロキシエチルメタクリレー
ト ５重量パーセントの共重合物よりなるコンタクトレ
ンズ成形体と接触角測定用の平板サンプルを電極間距離
3.5mm、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1mmのガラス２枚と、
厚み1.5mmのスペーサでつくった空間に設置し、放電処
理をおこなった。Example 1 60% by weight of methyl methacrylate, tris (trimethylsiloxy) silylpropyl methacrylate
35% by weight, 2-hydroxyethyl methacrylate 5% by weight of a copolymer made of a copolymer and a flat plate sample for measuring a contact angle between the electrodes
3.5mm, voltage between electrodes 15 kilovolts, frequency of 60 Hz Corona discharge treatment device with two 1mm thick glass between electrodes,
It was placed in a space made of spacers with a thickness of 1.5 mm and was subjected to discharge treatment.
処理したサンプルを、アクリルアミド/N,N′−メチレ
ンビスアクリルアミド（9/1 モル比）を含有する10重
量パーセントの水溶液に浸漬し、十分脱気した後、密閉
し、80分、60℃の恒温水槽に放置した。The treated sample is immersed in a 10% by weight aqueous solution containing acrylamide / N, N'-methylenebisacrylamide (9/1 molar ratio), sufficiently degassed, sealed, and kept at 60 ° C for 80 minutes. Left in the aquarium.
放置後、開封し、サンプルを取り出し、十分洗浄し
た。After standing, the container was opened, and the sample was taken out and washed sufficiently.
このようにして得られたサンプルの接触角は、処理前
の91度から23度へ改良された。The contact angle of the sample thus obtained was improved from 91 degrees before treatment to 23 degrees.
実際に装用したところ、従来のハードコンタクトレン
ズに比べ格段に優れたソフトレンズ並の装用感を有すコ
ンタクトレンズであった。When actually worn, it was a contact lens having a wearing sensation comparable to a soft lens, which is much better than a conventional hard contact lens.
（実施例２） 電極間６センチメートル、電極間電圧270ボルト、周
波数60ヘルツの放電処理装置にサンプルを設置し、0.04
トールのアルゴン雰囲気中で放電処理したあと、空気中
にだしてから実施例１と同様に処理した。(Example 2) A sample was placed in a discharge treatment apparatus having a distance of 6 cm between electrodes, a voltage of 270 volts between electrodes, and a frequency of 60 Hz.
After a discharge treatment in a torr argon atmosphere, the mixture was discharged into air and treated in the same manner as in Example 1.
その結果、接触角は91度から25度に改良された。 As a result, the contact angle was improved from 91 degrees to 25 degrees.
以上実施例を述べたが、この効果は実施例に限定され
るものでなく、コンタクトレンズ材料のモノマーの種類
や、その組成割合を代えても実施例と同様接触角を改良
することは可能である。Although the embodiment has been described above, this effect is not limited to the embodiment, and it is possible to improve the contact angle similarly to the embodiment by changing the type of the monomer of the contact lens material and the composition ratio thereof. is there.
また、アクリルアミド以外の親水性モノマーを用いて
も同様に改良することができる。In addition, similar improvements can be obtained by using a hydrophilic monomer other than acrylamide.
アクリルアミド以外の親水性モノマーとしてはN,N−
ジメチルアクリルアミド、２−ヒドロキシエチルメタク
リレート、２−ヒドロキシエチルアクリレート、アクリ
ル酸、Ｎ−ビニルヒロリドン、ポリエチレングリコール
モノメタクリレート、ポリエチレングリコールモノアク
リレート等が考えられる。この他に酢酸ビニル（親水性
モノマーではないが、適当な有機溶媒を使用する事によ
りグラフト化でき、最初ポリ酢酸ビニルとなりケン化す
る事によりポリビニルアルコールとなる。このためコン
タクトレンズの表面が濡れ易くなり初期の目的を達成す
る。）を使用することもできる。As hydrophilic monomers other than acrylamide, N, N-
Dimethyl acrylamide, 2-hydroxyethyl methacrylate, 2-hydroxyethyl acrylate, acrylic acid, N-vinyl hololidone, polyethylene glycol monomethacrylate, polyethylene glycol monoacrylate, and the like can be considered. In addition, vinyl acetate (not a hydrophilic monomer, but can be grafted by using a suitable organic solvent, becomes polyvinyl acetate first and becomes polyvinyl alcohol by saponification. Therefore, the surface of the contact lens is easily wetted. To achieve the initial purpose).
以上述べたように本発明によれば、濡れ性と装用感に
優れ、かつこの効果が長期にわたり持続するハードコン
タクトレンズが得られるという効果を有する。As described above, according to the present invention, it is possible to obtain a hard contact lens which is excellent in wettability and feeling of wearing, and in which this effect is maintained for a long time.
第１図は、本発明のコンタクトレンズの表面の概念を表
す図である。 １……コンタクトレンズ基材 ２……親水性ポリマーFIG. 1 is a view showing the concept of the surface of the contact lens of the present invention. 1 ... contact lens substrate 2 ... hydrophilic polymer
Claims (6)
ンタクトレンズ基材を水溶性モノマー溶液中で処理して
なるコンタクトレンズにおいて前記水溶性モノマーが１
官能性モノマーと２官能性モノマーの混合物であること
を特徴とするコンタクトレンズ。1. A contact lens obtained by treating a contact lens substrate exposed to an oxygen atmosphere after a plasma treatment in a water-soluble monomer solution, wherein the water-soluble monomer is 1%.
A contact lens, which is a mixture of a functional monomer and a bifunctional monomer.
−ジメチルアクリルアミド、２−ヒドロキシエチルメタ
クリレート、２−ヒドロキシエチルアクリレート、アク
リル酸、Ｎ−ビニルピロリドン、ポリエチレングリコー
ルモノメタクリレート、ポリエチレングリコールモノア
クリレート、酢酸ビニル（ポリ酢酸ビニルに変換され、
次でポリビニルアルコールに変換される）の一種以上よ
りなることを特徴とする請求項１記載のコンタクトレン
ズ。2. The monofunctional monomer is acrylamide, N, N
-Dimethylacrylamide, 2-hydroxyethyl methacrylate, 2-hydroxyethyl acrylate, acrylic acid, N-vinylpyrrolidone, polyethylene glycol monomethacrylate, polyethylene glycol monoacrylate, vinyl acetate (converted to polyvinyl acetate,
2. The contact lens according to claim 1, wherein the contact lens comprises at least one of the following:
アクリルアミドまたは、Ｎ′Ｎメチレンビスメタクリル
アミドであることを特徴とする請求項１記載のコンタク
トレンズ。3. The contact lens according to claim 1, wherein the bifunctional monomer is N, N'-methylenebisacrylamide or N'N methylenebismethacrylamide.
ル酸のエステル化合物のポリマーよりなることを特徴と
する請求項１記載のコンタクトレンズ。4. The contact lens according to claim 1, wherein the main component of the contact lens substrate is a polymer of an ester compound of methacrylic acid.
メタクリレート :Rはアルキル基を示す。） であることを特徴とする請求項４記載のコンタクトレン
ズ。5. The methacrylic acid ester compound is an alkyl methacrylate. : R represents an alkyl group. The contact lens according to claim 4, wherein
が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C1〜C5のアルキル基およびＺ基から
なる群より選ばれＺは構造式 をもつ基でありＡはC1〜C5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ことを特徴とする請求項４記載のコ
ンタクトレンズ。6. The polymer of an ester compound of methacrylic acid is an alkyl methacrylate and a siloxanyl methacrylate. (Wherein X and Y are selected from the group consisting of C 1 -C 5 alkyl groups and Z groups, and Z is a structural formula A group with A represents an alkyl group of C 1 -C 5. m, n
Represents 0 or a positive integer. The contact lens according to claim 4, wherein the contact lens is a copolymer of the following.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10067289A JP2881808B2 (en) | 1989-04-20 | 1989-04-20 | contact lens |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10067289A JP2881808B2 (en) | 1989-04-20 | 1989-04-20 | contact lens |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02278224A JPH02278224A (en) | 1990-11-14 |
| JP2881808B2 true JP2881808B2 (en) | 1999-04-12 |
Family
ID=14280256
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10067289A Expired - Fee Related JP2881808B2 (en) | 1989-04-20 | 1989-04-20 | contact lens |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2881808B2 (en) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5142553A (en) * | 1974-10-08 | 1976-04-10 | Hoya Lens Co Ltd | SHINSUISEISHIRIKOONKONTAKUTORENZUNO SEIZOHOHO |
| JPS6210616A (en) * | 1985-07-09 | 1987-01-19 | Seiko Epson Corp | contact lens |
-
1989
- 1989-04-20 JP JP10067289A patent/JP2881808B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH02278224A (en) | 1990-11-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |