JPS6229773B2 - - Google Patents
Info
- Publication number
- JPS6229773B2 JPS6229773B2 JP54173010A JP17301079A JPS6229773B2 JP S6229773 B2 JPS6229773 B2 JP S6229773B2 JP 54173010 A JP54173010 A JP 54173010A JP 17301079 A JP17301079 A JP 17301079A JP S6229773 B2 JPS6229773 B2 JP S6229773B2
- Authority
- JP
- Japan
- Prior art keywords
- chitosan
- lens
- chitin
- lenses
- derivatives
- 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
Links
- 229920001661 Chitosan Polymers 0.000 claims description 17
- 229920002101 Chitin Polymers 0.000 claims description 8
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 claims description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000463 material Substances 0.000 description 7
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- -1 hydroxybutyl Chemical group 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 239000002504 physiological saline solution Substances 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000006289 hydroxybenzyl group Chemical group 0.000 description 1
- 229940054190 hydroxypropyl chitosan Drugs 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- QUBQYFYWUJJAAK-UHFFFAOYSA-N oxymethurea Chemical compound OCNC(=O)NCO QUBQYFYWUJJAAK-UHFFFAOYSA-N 0.000 description 1
- 229950005308 oxymethurea Drugs 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002522 swelling effect Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Eyeglasses (AREA)
Description
【発明の詳細な説明】
本発明は新規な素材によるコンタクトレンズに
関するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a contact lens made of a novel material.
コンタクトレンズが使用され出してから既に二
十数年が経過しているが今迄使用されてきたもの
はすべて重合体からつくられたものであり、例え
ばポリメチルメタクリレート、ヒドロキシエチル
メタクリレート、シリコーン等である。 More than 20 years have passed since contact lenses were first used, but all the lenses used to date have been made from polymers, such as polymethyl methacrylate, hydroxyethyl methacrylate, and silicone. be.
これらのうち、軟質コンタクトレンズについて
は主としてOH基を有したアクリル系誘導体の単
独重合体又は共重合体が使用されており、レンズ
としての光学的性質、水を吸つて膨潤する膨潤性
が良好であつて装着時苦痛感が少ないこととあい
まつて好まれている。 Among these, soft contact lenses are mainly made of homopolymers or copolymers of acrylic derivatives having OH groups, which have good optical properties as lenses and swelling properties when absorbing water. It is preferred because it is warm and causes less pain when worn.
しかしながら従来の材質による、とりわけ軟質
コンタクトレンズは優れた性質を有する一方材質
がもろく物理的強度が弱いので取扱い中に割れた
り欠けたりする欠点があり、洗浄、消毒途中に割
れたり亀裂が入つて破損することがあつた。 However, while soft contact lenses made of conventional materials have excellent properties, they are brittle and have low physical strength, so they have the disadvantage of cracking or chipping during handling, or breakage or cracking during cleaning or disinfection. I had something to do.
本発明者らはキチン、キトサンもしくはこれら
の誘導体につきその合成法、分子構造、物理特
性、生化学特性に着目して種々検討中のところキ
チン、キトサンもしくはこれらの誘導体が上記し
たような欠点を伴わず極めて優れたコンタクトレ
ンズとなりうることを見出したものである。 The present inventors have been conducting various studies on chitin, chitosan, and their derivatives, focusing on their synthesis methods, molecular structures, physical properties, and biochemical properties, and have found that chitin, chitosan, and their derivatives have the above-mentioned drawbacks. We have discovered that this material can be used as an extremely excellent contact lens.
キチン、キトサンの誘導体としては、例えばア
セチルキチン、ヒドロキシエチルキトサン、ヒド
ロキシプロピルキトサン、ヒドロキシブチルキト
サン、ヒドロキシベンジルキトサン、ヒドロキシ
ヘキシルキトサン、アセチルキトサン等が挙げら
れるがこれらに限定されるものではない。 Examples of derivatives of chitin and chitosan include, but are not limited to, acetyl chitin, hydroxyethyl chitosan, hydroxypropyl chitosan, hydroxybutyl chitosan, hydroxybenzyl chitosan, hydroxyhexyl chitosan, and acetyl chitosan.
コンタクトレンズは上記素材の溶液をガラス、
金属などの型に入れて溶媒を除去することにより
成形される。本発明のコンタクトレンズは素材の
選択及び後での処理によつて硬いものも軟いもの
も適宜製造することが可能であるが、素材の特性
から軟質コンタクトレンズ用に、より優れた適性
を有するものである。 Contact lenses are made of glass, a solution of the above materials,
It is molded by placing it in a metal mold and removing the solvent. Although the contact lenses of the present invention can be made into either hard or soft lenses depending on the selection of materials and subsequent processing, they are more suitable for soft contact lenses due to the characteristics of the materials. It is something.
本発明に使用するキチン、キトサンもしくはこ
れらの誘導体は膜とか不織布に賦型して透析膜と
か創傷カバー材料としての使用が近年注目されて
いるものであるがコンタクトレンズへの使用例は
報告されていない。 Chitin, chitosan, or their derivatives used in the present invention have recently attracted attention for use as dialysis membranes or wound covering materials by forming them into membranes or nonwoven fabrics, but no examples of their use in contact lenses have been reported. do not have.
キチンは蟹の甲羅などに含まれる天然高分子物
質であつて広く自然界から容易に入手しうるもの
であり、キトサンはそれを脱アセチル化したもの
であつて、いずれも市販品から容易に入手するこ
とが出来る原料である。 Chitin is a natural polymer substance found in crab shells, etc., and is widely available in nature. Chitosan is deacetylated chitosan, and both are easily obtained from commercial products. It is a raw material that can be
キトサンは酢酸、ギ酸、プロピオン酸等に溶解
してレンズに成形後水酸化ナトリウム処理するこ
とにより、又キチンはトリクロル酢酸とジクロル
メタンの混合系の他に塩化リチウムや塩化カルシ
ウムを含むジメチルアセトアミド、メチルセロソ
ルブ、N−メチルピロリドン等の極性有機溶媒に
溶解させてレンズに成型する。 Chitosan can be produced by dissolving it in acetic acid, formic acid, propionic acid, etc., molding it into a lens, and then treating it with sodium hydroxide.Chitin can also be produced by dissolving it in acetic acid, formic acid, propionic acid, etc. and treating it with sodium hydroxide after forming it into a lens. , N-methylpyrrolidone or other polar organic solvent and molded into a lens.
ヒドロキシエチルキトサン等の誘導体は溶媒中
で架橋剤、例えばジメチロール尿素、トリレンジ
イソシアネート、エピクロルヒドリン、ホルムア
ルデヒド、アセトアルデヒド、メチロールアクリ
ルアミド、グルタルアルデヒド、クロム酸等と接
触させてから加熱することにより架橋が行なわれ
て水に不溶で強度の向上したものとすることも可
能である。 Derivatives such as hydroxyethyl chitosan are crosslinked by contacting them with a crosslinking agent such as dimethylol urea, tolylene diisocyanate, epichlorohydrin, formaldehyde, acetaldehyde, methylol acrylamide, glutaraldehyde, chromic acid, etc. in a solvent and then heating. It is also possible to make it insoluble in water and have improved strength.
あるいはガンマ線、紫外線等の照射を行なうこ
とによつても架橋を行なうことが出来る。 Alternatively, crosslinking can also be effected by irradiation with gamma rays, ultraviolet rays, or the like.
次に本発明を実施例により説明する。 Next, the present invention will be explained by examples.
実施例 1
市販のキトサンを水洗浄後エタノール、エーテ
ルで洗浄してから乾燥し、1.5%酢酸水溶液に1
%の割合で溶解し、グルタルアルデヒドを0.1%
の割合で添加した。これをガラス製の下側レンズ
型に入れて均一に拡げ、次に減圧下で一昼夜脱気
して上側レンズ型の凸部をキトサンを収容した下
側型に押しつけ、型金体を加熱オーブンに移し、
70℃で10時間加熱して架橋した。こうして形成し
たキトサンレンズを稀水酸化ナトリウム水溶液
(PH8)で中和し、生理食塩水に移して放置後と
り出して凍結させてレンズの周囲を円形のカツタ
ーで切断した。仕上つたレンズは生理食塩水中に
保存した。このレンズは光学的に透明であり、柔
軟性に富み、コンタクトレンズとして優れた特性
を示した。Example 1 Commercially available chitosan was washed with water, then washed with ethanol and ether, dried, and diluted with 1.5% acetic acid aqueous solution.
Dissolve glutaraldehyde at a rate of 0.1%
It was added at a ratio of This was placed in a lower glass lens mold and spread uniformly, then degassed under reduced pressure overnight, the convex part of the upper lens mold was pressed against the lower mold containing chitosan, and the mold body was placed in a heating oven. Transfer,
Crosslinking was achieved by heating at 70°C for 10 hours. The chitosan lens thus formed was neutralized with a dilute aqueous sodium hydroxide solution (PH8), transferred to physiological saline, left to stand, taken out, frozen, and cut around the lens with a circular cutter. The finished lenses were stored in physiological saline. This lens was optically transparent and highly flexible, and exhibited excellent properties as a contact lens.
第1図は本発明のコンタクトレンズの実施例を
示す正面図、第2図はその断面図である。
FIG. 1 is a front view showing an embodiment of the contact lens of the present invention, and FIG. 2 is a sectional view thereof.
Claims (1)
ら成るコンタクトレンズ。 2 ホルムアルデヒド、グルタルアルデヒドもし
くはエピクロルヒドリンで処理して架橋させた特
許請求の範囲第1項記載のコンタクトレンズ。[Claims] 1. A contact lens made of chitin, chitosan, or a derivative thereof. 2. The contact lens according to claim 1, which is crosslinked by treatment with formaldehyde, glutaraldehyde, or epichlorohydrin.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP17301079A JPS5694322A (en) | 1979-12-27 | 1979-12-27 | Contact lens |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP17301079A JPS5694322A (en) | 1979-12-27 | 1979-12-27 | Contact lens |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5694322A JPS5694322A (en) | 1981-07-30 |
JPS6229773B2 true JPS6229773B2 (en) | 1987-06-29 |
Family
ID=15952516
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP17301079A Granted JPS5694322A (en) | 1979-12-27 | 1979-12-27 | Contact lens |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS5694322A (en) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4532267A (en) * | 1984-02-15 | 1985-07-30 | Board Of Regents, University Of Washington | Vision correction lens made from an aminopolysaccharide compound or an ether or ester thereof |
JP2564520B2 (en) * | 1986-08-21 | 1996-12-18 | ユニチカ株式会社 | Contact lens manufacturing method |
JP2615038B2 (en) * | 1987-03-05 | 1997-05-28 | ユニチカ株式会社 | Method for producing chitin molded article |
KR960702624A (en) * | 1994-03-14 | 1996-04-27 | 야마타니 와타루 | Material to be worn on the eyeball |
US5789462A (en) * | 1995-09-13 | 1998-08-04 | Seikagaku Kogyo Kabushiki Kaisha (Seikagaku Corporation) | Photocured crosslinked-hyaluronic acid contact lens |
JP3947391B2 (en) | 2001-11-28 | 2007-07-18 | 独立行政法人 日本原子力研究開発機構 | Method for producing chitin derivative and / or chitosan derivative having bridge structure |
-
1979
- 1979-12-27 JP JP17301079A patent/JPS5694322A/en active Granted
Non-Patent Citations (1)
Title |
---|
RICCARDO A.A.MUZZARERLLI.CHITIN=1977 * |
Also Published As
Publication number | Publication date |
---|---|
JPS5694322A (en) | 1981-07-30 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CA1158463A (en) | Collagen contact lens | |
JPH03196116A (en) | Lens from arcrylic acid and methacrylic acid | |
US7307157B2 (en) | Process for producing chitin derivatives and/or chitosan derivatives having a crosslinked structure | |
CN109369948B (en) | Bacterial cellulose/polyvinyl alcohol antibacterial hydrogel and preparation method and application thereof | |
JPH0730124B2 (en) | Cross-linked hyaluronic acid moldings | |
US4532267A (en) | Vision correction lens made from an aminopolysaccharide compound or an ether or ester thereof | |
KR102347902B1 (en) | A human insert type dilator using dual-network structured hydrogel | |
JPS6229773B2 (en) | ||
CN113980185B (en) | Amorphous silver-containing long-acting antibacterial hydrogel dressing with photocrosslinking curing function and preparation method thereof | |
JPS5823410B2 (en) | Hydrogel Youkizai | |
JPS5825764B2 (en) | Polyvinyl alcohol | |
CN109851846B (en) | Antibacterial sodium alginate cross-linked sponge and preparation method and application thereof | |
JPH02109570A (en) | Silkfibroin-containing molding | |
JPS63220111A (en) | Contact or internal eye lens made of polymer or copolymer slightly crosslinked by 2-hydroxyethylmethacrylate and manufacture thereof | |
GB1602339A (en) | Collagen skin dressings | |
KR102046263B1 (en) | Process Of Producing Regenerated Protain Fiber Having Excellent Water-fastness | |
US5322648A (en) | Process for forming shaped collagen devices | |
WO2001068746A1 (en) | Molding made of polyvinyl alcohol and process for producing the same | |
JP2000157625A (en) | Polyvinyl alcohol-made medical hydrogel and manufacture therefor | |
JP2564520B2 (en) | Contact lens manufacturing method | |
JPH0613586B2 (en) | High absorbent material | |
CN107854721B (en) | Antibacterial hydrogel and preparation method thereof | |
JPH09165404A (en) | Chitosan molding with its surface being n-thiocarbamoylated and its production | |
JP2615038B2 (en) | Method for producing chitin molded article | |
JPS5919122B2 (en) | Water-soluble partially deacetylated chitin and its production method |