JP2006163008A - Contact lens cleaning agent - Google Patents
Contact lens cleaning agent Download PDFInfo
- Publication number
- JP2006163008A JP2006163008A JP2004354845A JP2004354845A JP2006163008A JP 2006163008 A JP2006163008 A JP 2006163008A JP 2004354845 A JP2004354845 A JP 2004354845A JP 2004354845 A JP2004354845 A JP 2004354845A JP 2006163008 A JP2006163008 A JP 2006163008A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- group
- contact lens
- chain
- component
- 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
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- 239000012459 cleaning agent Substances 0.000 title claims abstract description 32
- 150000001875 compounds Chemical class 0.000 claims abstract description 60
- 150000003839 salts Chemical class 0.000 claims description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 125000002252 acyl group Chemical group 0.000 claims description 12
- 229910019142 PO4 Inorganic materials 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- 125000000524 functional group Chemical group 0.000 claims description 11
- 239000010452 phosphate Substances 0.000 claims description 11
- 125000001165 hydrophobic group Chemical group 0.000 claims description 10
- 125000004122 cyclic group Chemical group 0.000 claims description 8
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 8
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- 238000000034 method Methods 0.000 claims description 6
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- 125000006850 spacer group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
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- 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 5
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 125000000539 amino acid group Chemical group 0.000 claims description 2
- 238000007598 dipping method Methods 0.000 claims description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 2
- 238000004140 cleaning Methods 0.000 abstract description 9
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- 125000003277 amino group Chemical group 0.000 description 13
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Landscapes
- Eyeglasses (AREA)
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Abstract
Description
本発明は、多鎖多親水基型化合物を含有してなるコンタクトレンズ洗浄剤に関する。 The present invention relates to a contact lens cleaner comprising a multi-chain polyhydrophilic group type compound.
従来より、ソフトおよびハードコンタクトレンズの洗浄液は汚れの洗浄性とともに安全性が重視されており、洗浄性を向上させるために、タンパク分解酵素や脂質分解酵素を配合することが試みられている。しかしながら、酵素は水中での安定性に乏しく、また酵素の配合のみでは洗浄力が不十分であり、また酵素を多量に添加するとアレルギー反応等や皮膚等への刺激が起こりやすくなるおそれがある。
例えば、特許文献1には、多価アルコール類を加えることで酵素の液中での安定性を高める技術が開示している。しかしこの技術では、界面活性剤の存在による酵素活性の低下を防ぐことはできず、界面活性剤を洗浄液に配合せず希釈液に配合させて、洗浄直前に洗浄液と希釈液を混合させる方法を採用している。洗浄力を高めるために界面活性剤の配合が必要であるが、アニオン界面活性剤以外を用いた場合には洗浄力が不十分であるとともに、アニオン界面活性剤は皮膚等への刺激性が大きく、かつ酵素の安定性を著しく低下させるという問題がある。
また、特にハードコンタクトレンズの場合、表面の疎水性が高いために装着時の目の乾燥感や異物感が高いという問題点があり、コンタクトレンズ洗浄剤に対しては、洗浄性とともにレンズ表面の親水性を高め乾燥感や異物感を軽減することが求められている。
Conventionally, soft and hard contact lens cleaning liquids have been given importance to safety as well as dirt cleaning properties, and attempts have been made to add proteolytic enzymes and lipolytic enzymes in order to improve the cleaning properties. However, the enzyme has poor stability in water, and the detergency of the enzyme alone is insufficient, and if the enzyme is added in a large amount, an allergic reaction or irritation to the skin may occur easily.
For example, Patent Document 1 discloses a technique for increasing the stability of an enzyme in a liquid by adding a polyhydric alcohol. However, this technique cannot prevent a decrease in enzyme activity due to the presence of a surfactant, and a method in which a surfactant is not mixed with a cleaning solution but mixed with a diluent, and the cleaning solution and the diluted solution are mixed immediately before cleaning. Adopted. In order to enhance the detergency, it is necessary to add a surfactant. However, when other than an anionic surfactant is used, the detergency is insufficient and the anionic surfactant is highly irritating to the skin. And there is a problem that the stability of the enzyme is significantly reduced.
In particular, in the case of hard contact lenses, there is a problem in that the surface is highly hydrophobic and the eyes feel dry and foreign matter is high. There is a demand for increasing hydrophilicity and reducing the feeling of dryness and foreign matter.
本発明は、コンタクトレンズの洗浄性と皮膚等への安全性に優れ、装着時の目の乾燥感や異物感を軽減できるようなコンタクトレンズ洗浄剤の提供を目的とするものである。 An object of the present invention is to provide a contact lens cleaning agent that is excellent in the cleanability of contact lenses and the safety to the skin, etc., and can reduce the feeling of dryness of eyes and the feeling of foreign matters during wearing.
本発明者は、前記課題を解決すべく鋭意検討を重ねた結果、特定の化合物、即ち、分子内に長鎖疎水基と親水基とを2個以上づつ有する化合物、即ち多鎖多親水基型化合物に着目し、これを配合することで、酵素安定性を保持したまま洗浄性に優れ、装着時の目の乾燥感や異物感を軽減できることを見出した。また、多鎖多親水基型化合物は、刺激緩和効果を有することから、これを配合した洗浄剤は皮膚等への刺激も非常に低く安全性に優れたコンタクトレンズ洗浄剤となることを見出し、本発明を完成するに至った。
即ち本発明は、下記の通りである。
1.成分(A):長鎖疎水基と親水基とを分子内に2個以上づつ有する多鎖多親水基型化合物の少なくとも1種を含有することを特徴とするコンタクトレンズ洗浄剤。
2.多鎖多親水基型化合物の少なくとも1種が、その長鎖疎水基が長鎖アシル基であり、親水基がカルボキシル基、スルホン酸基、硫酸エステル基、リン酸エステル基またはそれらの塩であることを特徴とする上記1.に記載のコンタクトレンズ洗浄剤。
3.多鎖多親水基型化合物の少なくとも1種が、分子内にアミノ酸残基を有するものであることを特徴とする上記1.または2.に記載のコンタクトレンズ洗浄剤。
4.多鎖多親水基型化合物の少なくとも1種が、下記一般式(1)で示される化合物であることを特徴とする上記1.〜3.のいずれかに記載のコンタクトレンズ洗浄剤。
5.多鎖多親水基型化合物の少なくとも1種が、一般式(1)に示す化合物であって、一般式(1)中、Xは前記官能基以外の置換基を有していてもよい炭素数1〜40の直鎖または分枝鎖または環状鎖または芳香族炭化水素鎖であるスペーサーであることを特徴とする上記1.〜4.のいずれかに記載のコンタクトレンズ洗浄剤。
6.さらに、成分(B):保湿性成分、成分(C):加水分解酵素、成分(D):ホウ素化合物を含有することを特徴とする上記1.〜5.のいずれかに記載のコンタクトレンズ洗浄剤。
7.成分(A):多鎖多親水基型化合物が0.01〜5質量%、成分(B):保湿性成分が3〜50質量%、成分(C):加水分解酵素が0.0001〜10質量%、成分(D):ホウ素化合物が0.1〜10質量%であることを特徴とする上記1.〜6.のいずれかに記載のコンタクトレンズ洗浄剤。
8.上記1.〜7.のいずれかに記載のコンタクトレンズ洗浄剤を用いて、コンタクトレンズを浸漬処理することを特徴とするコンタクトレンズの処理方法。
As a result of intensive studies to solve the above problems, the present inventor has obtained a specific compound, that is, a compound having two or more long-chain hydrophobic groups and hydrophilic groups in the molecule, that is, a multi-chain multi-hydrophilic group type. By paying attention to the compound and blending it, it was found that it was excellent in cleanability while maintaining enzyme stability, and that it was possible to reduce the dryness of the eyes and the feeling of foreign matter at the time of wearing. In addition, since the multi-chain polyhydrophilic group type compound has an irritation mitigating effect, it has been found that a cleaning agent formulated with the compound is a contact lens cleaning agent with extremely low irritation to the skin and the like, and excellent in safety. The present invention has been completed.
That is, the present invention is as follows.
1. Component (A): A contact lens cleaning agent comprising at least one multi-chain polyhydrophilic group type compound having two or more long-chain hydrophobic groups and hydrophilic groups in the molecule.
2. At least one of the multi-chain poly-hydrophilic group type compound, the long-chain hydrophobic group is a long-chain acyl group, and the hydrophilic group is a carboxyl group, a sulfonic acid group, a sulfate ester group, a phosphate ester group or a salt thereof The above 1. Contact lens cleaning agent according to 1.
3. At least one of the multi-chain polyhydrophilic group type compounds has an amino acid residue in the molecule. Or 2. Contact lens cleaning agent according to 1.
4). At least one of the multi-chain polyhydrophilic group type compounds is a compound represented by the following general formula (1): ~ 3. The contact lens cleaning agent according to any one of the above.
5. At least one of the multi-chain polyhydrophilic group type compound is a compound represented by the general formula (1), and in the general formula (1), X may have a substituent other than the functional group. 1 to 40, which is a spacer which is a straight chain, branched chain, cyclic chain or aromatic hydrocarbon chain. ~ 4. The contact lens cleaning agent according to any one of the above.
6). Furthermore, component (B): a moisturizing component, component (C): a hydrolase, component (D): a boron compound is contained. ~ 5. The contact lens cleaner according to any one of the above.
7). Component (A): 0.01 to 5% by mass of multi-chain polyhydrophilic group type compound, Component (B): 3 to 50% by mass of moisturizing component, Component (C): 0.0001 to 10 of hydrolase 1.% by mass, component (D): 0.1 to 10% by mass of a boron compound. ~ 6. The contact lens cleaner according to any one of the above.
8). Above 1. ~ 7. A contact lens treatment method comprising: dipping a contact lens using the contact lens cleaning agent according to any one of the above.
本発明によるコンタクトレンズ洗浄剤は、洗浄性と皮膚等への安全性に優れ、装着時の目の乾燥感や異物感を軽減できるという顕著な効果を有する。 The contact lens cleaning agent according to the present invention is excellent in cleanability and safety to the skin and the like, and has a remarkable effect that it can reduce the dryness of the eyes and the feeling of foreign matter when worn.
以下、本発明について具体的に説明する。
本発明のコンタクトレンズ洗浄剤は、構造的には分子内に長鎖疎水基と親水基とを2個以上づつ有する多鎖多親水基型化合物の少なくとも1種を含んでなる組成物である。
本発明のコンタクトレンズ洗浄剤における多鎖多親水基型化合物としては、長鎖疎水基としてはそれぞれ独立に、炭素数8〜20個の飽和または不飽和の直鎖、分枝鎖、環状鎖からなる疎水基を有し、親水基としてはそれぞれ独立に、カルボキシル基、スルホン酸基、硫酸残基、リン酸残基またはそれらの塩等、あるいはオキシアルキレン基、ポリエチレングリコール基等、またはアミノ基、4級アンモニウム基、ピリジニウム基、スルホニウム基またはそれらの塩等を有するものである。
例えば、多鎖多親水基化合物の長鎖疎水基としては、例えば、n−オクチル、n−ノニル、n−デシル、n−ウンデシル、n−ドデシル、n−トリデシル、n−テトラデシル、n−ペンタデシル、n−ヘキサデシル、n−ヘプタデシル、n−オクタデシル、n−ノナデシル、n−エイコシル等の各残基とこれらの分枝鎖異性体、ならびにこれらに対応した、1カ所、2カ所または3カ所に不飽和部分を有する不飽和残基等が挙げられる。
また、多鎖多親水基型化合物の長鎖疎水基としては、炭素数8〜20の飽和または不飽和の脂肪酸から誘導される長鎖アシル基であり、アシル基としては、それぞれ、独立して、すなわち、それぞれ異なっても同一でもよい。
Hereinafter, the present invention will be specifically described.
The contact lens cleaner of the present invention is structurally a composition comprising at least one multi-chain polyhydrophilic group type compound having two or more long-chain hydrophobic groups and hydrophilic groups in the molecule.
As the multi-chain polyhydrophilic group-type compound in the contact lens cleaning agent of the present invention, each long-chain hydrophobic group is independently a saturated or unsaturated linear, branched, or cyclic chain having 8 to 20 carbon atoms. Each of the hydrophilic groups independently includes a carboxyl group, a sulfonic acid group, a sulfuric acid residue, a phosphoric acid residue or a salt thereof, an oxyalkylene group, a polyethylene glycol group, or the like, or an amino group, It has a quaternary ammonium group, a pyridinium group, a sulfonium group or a salt thereof.
For example, as the long-chain hydrophobic group of the multi-chain polyhydrophilic group compound, for example, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, Residues such as n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, etc. and branched isomers thereof, and corresponding one, two or three unsaturated sites And an unsaturated residue having a moiety.
In addition, the long-chain hydrophobic group of the multi-chain polyhydrophilic group type compound is a long-chain acyl group derived from a saturated or unsaturated fatty acid having 8 to 20 carbon atoms. That is, they may be different or the same.
例えば、カプリル酸、ペラルゴン酸、カプリン酸、ウンデカン酸、ラウリン酸、トリデカン酸、ミリスチン酸、ペンタデカン酸、パルミチン酸、マルガリン酸、ステアリン酸、ノナデカン酸、アラキン酸のような直鎖脂肪酸;
2−ブチル−5−メチルペンタン酸、2−イソブチル−5−メチルペンタン酸、ジメチルオクタン酸、ジメチルノナン酸、2−ブチル−5−メチルヘキサン酸、メチルウンデカン酸、ジメチルデカン酸、2−エチル−3−メチルノナン酸、2,2−ジメチル−4−エチルオクタン酸、メチルドコサン酸、2−プロピル−3−メチルノナン酸、メチルトリデカン酸、ジメチルドデカン酸、2−ブチル−3−メチルノナン酸、メチルテトラデカン酸、エチルトリデカン酸、プロピルドデカン酸、ブチルウンデカン酸、ペンチルデカン酸、ヘキシルノナン酸、2−(3−メチルブチル)−3−メチルノナン酸、2−(2−メチルブチル)−3−メチルノナン酸、ブチルエチルノナン酸、メチルペンタデカン酸、エチルテトラデカン酸、プロピルトリデカン酸、ブチルドデカン酸、ペンチルウンデカン酸、ヘキシルデカン酸、ヘプチルノナン酸、ジメチルテトラデカン酸、ブチルペンチルヘプタン酸、トリメチルトリデカン酸、メチルヘキサデカン酸、エチルペンタデカン酸、プロピルテトラデカン酸、ブチルトリデカン酸、ペンチルドデカン酸、ヘキシルウンデカン酸、ヘプチルデカン酸、メチルヘプチルノナン酸、ジペンチルヘプタン酸、メチルヘプタデカン酸、エチルヘキサデカン酸、エチルヘキサデカン酸、プロピルペンタデカン酸、ブチルテトラデカン酸、ペンチルトリデカン酸、ヘキシルドデカン酸、ヘプチルウンデカン酸、オクチルデカン酸、ジメチルヘキサデカン酸、メチルオクチルノナン酸、メチルオクタデカン酸、エチルヘプタデカン酸、ジメチルヘプタデカン酸、メチルオクチルデカン酸、メチルノナデカン酸、メチルノナデカン酸、ジメチルオクタデカン酸、ブチルヘプチルノナン酸のような分岐脂肪酸;
オクテン酸、ノネン酸、デセン酸、カプロレイン酸、ウンデシレン酸、リンデル酸、トウハク酸、ラウロレイン酸、トリデセン酸、ツズ酸、ミリストレイン酸、ペンタデセン酸、ヘキセデセン酸、パルミトレイン酸、ヘプタデセン酸、オクタデセン酸、オレイン酸、ノナデセン酸、ゴンドイン酸のような直鎖モノエン酸;
メチルヘプテン酸、メチルノネン酸、メチルウンデセン酸、ジメチルデセン酸、メチルドデセン酸、メチルトリデセン酸、ジメチルドデセン酸、ジメチルトリデセン酸、メチルオクタデセン酸、ジメチルヘプタデセン酸、エチルオクタデセン酸のような分岐モノエン酸;
リノール酸、リノエライジン酸、エレオステアリン酸、リノレン酸、リノレンエライジン酸、プソイドエレオステアリン酸、パリナリン酸、アラキドン酸のようなジまたはトリエン酸;
オクチン酸、ノニン酸、デシン酸、ウンデシン酸、ドデシン酸、トリデシン酸、テトラデシン酸、ペンタデシン酸、ヘプタデシン酸、オクタデシン酸、ノナデシン酸、ジメチルオクタデシン酸のようなアセチレン酸;
メチレンオクタデセン酸、メチレンオクタデカン酸、アレプロール酸、アレプレスチン酸、アレプリル酸、アレプリン酸、ヒドノカルプン酸、ショールムーグリン酸、ゴルリン酸、α−シクロペンチル酸、α−シクロヘキシル酸、α−シクロペンチルエチル酸のような環状酸;
から誘導されるアシル基が挙げられる。
For example, linear fatty acids such as caprylic acid, pelargonic acid, capric acid, undecanoic acid, lauric acid, tridecanoic acid, myristic acid, pentadecanoic acid, palmitic acid, margaric acid, stearic acid, nonadecanoic acid, arachidic acid;
2-butyl-5-methylpentanoic acid, 2-isobutyl-5-methylpentanoic acid, dimethyloctanoic acid, dimethylnonanoic acid, 2-butyl-5-methylhexanoic acid, methylundecanoic acid, dimethyldecanoic acid, 2-ethyl- 3-methylnonanoic acid, 2,2-dimethyl-4-ethyloctanoic acid, methyldocosanoic acid, 2-propyl-3-methylnonanoic acid, methyltridecanoic acid, dimethyldodecanoic acid, 2-butyl-3-methylnonanoic acid, methyltetradecanoic acid , Ethyltridecanoic acid, propyldodecanoic acid, butylundecanoic acid, pentyldecanoic acid, hexylnonanoic acid, 2- (3-methylbutyl) -3-methylnonanoic acid, 2- (2-methylbutyl) -3-methylnonanoic acid, butylethylnonane Acid, methylpentadecanoic acid, ethyltetradecanoic acid, propyltri Canic acid, butyldodecanoic acid, pentylundecanoic acid, hexyldecanoic acid, heptylnonanoic acid, dimethyltetradecanoic acid, butylpentylheptanoic acid, trimethyltridecanoic acid, methylhexadecanoic acid, ethylpentadecanoic acid, propyltetradecanoic acid, butyltridecanoic acid, pentyldodecane Acid, hexylundecanoic acid, heptyldecanoic acid, methylheptylnonanoic acid, dipentylheptanoic acid, methylheptadecanoic acid, ethylhexadecanoic acid, ethylhexadecanoic acid, propylpentadecanoic acid, butyltetradecanoic acid, pentyltridecanoic acid, hexyldodecanoic acid, heptyl Undecanoic acid, octyldecanoic acid, dimethylhexadecanoic acid, methyloctylnonanoic acid, methyloctadecanoic acid, ethylheptadecanoic acid, dimethylheptadecanoic acid, Octyl decanoic acid, Mechirunonadekan acid, Mechirunonadekan acid, dimethyl octadecanoic acid, branched fatty acids such as butyl heptyl nonanoic acid;
Octenoic acid, nonenoic acid, decenoic acid, caproleic acid, undecylenic acid, Lindellic acid, touric acid, lauroleic acid, tridecenoic acid, tuzuic acid, myristoleic acid, pentadecenoic acid, hexedenoic acid, palmitoleic acid, heptadecenoic acid, octadecenoic acid, Linear monoenoic acids such as oleic acid, nonadecenoic acid, gondoic acid;
Such as methylheptenoic acid, methylnonenoic acid, methylundecenoic acid, dimethyldecenoic acid, methyldodecenoic acid, methyltridecenoic acid, dimethyldodecenoic acid, dimethyltridecenoic acid, methyloctadecenoic acid, dimethylheptadecenoic acid, ethyloctadecenoic acid Branched monoenoic acid;
Di- or trienoic acids such as linoleic acid, linoleic acid, eleostearic acid, linolenic acid, linolenic elaidic acid, pseudoeleostearic acid, parinaric acid, arachidonic acid;
Acetylene acids such as octinoic acid, nonic acid, decinic acid, undecinic acid, dodecinic acid, tridecinic acid, tetradecinic acid, pentadecinic acid, heptadesinic acid, octadecinic acid, nonadesinic acid, dimethyloctadesinic acid;
Of methyleneoctadecenoic acid, methyleneoctadecanoic acid, aleprolic acid, alepresinic acid, allepuric acid, alepuric acid, hydnocarpic acid, shoulmuric acid, gorulic acid, α-cyclopentylic acid, α-cyclohexylic acid, α-cyclopentylethylic acid Cyclic acids such as;
An acyl group derived from is mentioned.
また、天然油脂から得られる脂肪酸由来のアシル基でも良く、上記の炭素数8〜20の飽和または不飽和脂肪酸を80%以上含む混合脂肪酸由来のアシル基が好ましい。例えば、ヤシ油脂肪酸、パーム油脂肪酸、アマニ油脂肪酸、ヒマワリ油脂肪酸、大豆油脂肪酸、ゴマ油脂肪酸、ヒマシ油脂肪酸、オリーブ油脂肪酸、ツバキ油脂肪酸、菜種油脂肪酸、パーム核油脂肪酸等から誘導されるアシル基等が挙げられる。これらアシル化合物は2種以上組み合わせて用いても良い。
多鎖多親水基型化合物を塩として用いる場合には、例えば、アルカリ金属塩、アルカリ土類金属塩、アンモニウム塩、有機アミン塩、塩基性アミノ酸塩等が挙げられ、具体的には、ナトリウム、カリウム、リチウム等のアルカリ金属、カルシウム、マグネシウム等のアルカリ土類金属、アルミニウム、亜鉛等の金属、アンモニア、モノエタノールアミン、ジエタノールアミン、トリエタノールアミン、トリイソプロパノールアミン等の有機アミン、アルギニン、リジン等の塩基性アミノ酸等から任意に選ばれる1種または2種以上との塩である。これらの中でも、ナトリウム塩、カリウム塩、有機アミン塩、塩基性アミノ酸塩が特に好ましい。
Moreover, the acyl group derived from the fatty acid obtained from natural fats and oils may be sufficient, and the acyl group derived from the mixed fatty acid containing 80% or more of the above saturated or unsaturated fatty acid having 8 to 20 carbon atoms is preferable. For example, acyl groups derived from coconut oil fatty acid, palm oil fatty acid, linseed oil fatty acid, sunflower oil fatty acid, soybean oil fatty acid, sesame oil fatty acid, castor oil fatty acid, olive oil fatty acid, camellia oil fatty acid, rapeseed oil fatty acid, palm kernel oil fatty acid, etc. Etc. Two or more of these acyl compounds may be used in combination.
When using a multi-chain polyhydrophilic group type compound as a salt, for example, an alkali metal salt, an alkaline earth metal salt, an ammonium salt, an organic amine salt, a basic amino acid salt and the like can be mentioned. Alkaline metals such as potassium and lithium, alkaline earth metals such as calcium and magnesium, metals such as aluminum and zinc, organic amines such as ammonia, monoethanolamine, diethanolamine, triethanolamine and triisopropanolamine, arginine and lysine It is a salt with one or more kinds arbitrarily selected from basic amino acids and the like. Among these, sodium salts, potassium salts, organic amine salts, and basic amino acid salts are particularly preferable.
本発明において、コンタクトレンズ洗浄剤に含有される多鎖多親水基型化合物の少なくとも1種が一般式(1)および(2)で示されるアシル化合物であることが好ましい。
ここでいうアシル化合物とは、構造的には一般式(1)および(2)に示すように分子内に少なくとも1個以上のアシル基と親水基とを有する化合物を適当なスペーサーで連結した構造の化合物である。
一般式(2)中、R1COで示されるアシル基は独立して、すなわち、それぞれ異なっても同一でもよく、上記したように炭素数8〜20の飽和または不飽和の脂肪酸から誘導されるものであれば何でも良く、直鎖、分岐、環状を問わない。
一般式(2)中、R2は水素であるか、またはヒドロキシル基またはカルボキシル基、スルホン酸基、硫酸エステル基、リン酸エステル基またはそれらの塩等が置換していてもよい炭素数1〜3の低級アルキル基を示し、例えば、メチル基、エチル基、プロピル基、イソプロピル基、ヒドロキシメチル基、ヒドロキシエチル基、ヒドロキシ(イソ)プロピル基、ジヒドロキシ(イソ)プロピル基、カルボキシメチル基、カルボキシエチル基、カルボキシプロピル基、スルホエチル基等が挙げられる。
一般式(1)中、Xに結合したn個の置換基Q(式(2)で表される。)は、それぞれ互いに、異なっても同一でもよい。また、式(2)で表される基は、いわゆる酸性アミノ酸がN−アシル化された基を示すものであり、それらは光学異性体、例えば、D−体、L−体、ラセミ体であるかは問わない。
In the present invention, it is preferable that at least one of the multi-chain polyhydrophilic group compounds contained in the contact lens cleaner is an acyl compound represented by the general formulas (1) and (2).
The term “acyl compound” as used herein refers to a structure in which compounds having at least one acyl group and a hydrophilic group in the molecule are linked with an appropriate spacer as shown in the general formulas (1) and (2). It is a compound of this.
In the general formula (2), the acyl groups represented by R 1 CO are independent, that is, they may be different or the same, and are derived from a saturated or unsaturated fatty acid having 8 to 20 carbon atoms as described above. Anything can be used as long as it is linear, branched or cyclic.
In general formula (2), R 2 is hydrogen, or a hydroxyl group or a carboxyl group, a sulfonic acid group, a sulfuric ester group, a phosphoric ester group or a salt thereof, which may be substituted, 3 lower alkyl groups, for example, methyl group, ethyl group, propyl group, isopropyl group, hydroxymethyl group, hydroxyethyl group, hydroxy (iso) propyl group, dihydroxy (iso) propyl group, carboxymethyl group, carboxyethyl Group, carboxypropyl group, sulfoethyl group and the like.
In the general formula (1), n substituents Q (represented by the formula (2)) bonded to X may be different or the same. Further, the group represented by the formula (2) represents a group in which a so-called acidic amino acid is N-acylated, and they are optical isomers, for example, D-form, L-form, and racemate. It doesn't matter.
酸性アミノ酸は、分子中に存在するカルボキシル基とアミノ基の数がそれぞれ2個と1個のモノアミノジカルボン酸であり、アミノ基はN−メチル基またはN−エチル基でもかまわない。また光学異性体、例えば、D−体、L−体、ラセミ体であるかは問わない。酸性アミノ酸としては、例えば、グルタミン酸、アスパラギン酸、ランチオニン、β−メチルランチオニン、シスタチオニン、ジエンコール酸、フェリニン、アミノマロン酸、β−オキシアスパラギン酸、α−アミノ−α−メチルコハク酸、β−オキシグルタミン酸、γ−オキシグルタミン酸、γ−メチルグルタミン酸、γ−メチレングルタミン酸、γ−メチル−γ−オキシグルタミン酸、α−アミノアジピン酸、α−アミノ−γ−オキシアジピン酸、α−アミノピメリン酸、α−アミノ−γ−オキシピメリン酸、β−アミノピメリン酸、α−アミノスベリン酸、α−アミノセバシン酸、パントテン酸等が挙げられる。
Xに結合する付くn個の置換基Q(式(2)で表される。)は、酸性アミノ酸がL−酸性アミノ酸分子である場合が、生分解性に優れることから好ましい。
一般式(2)中、Zは、Xに置換したm個(m≧n、かつ、2〜20の整数)の官能基(ヒドロキシル基、アミノ基、チオール基)に由来する結合部(−O−、−NR3−、−S−)である。ここで、R3は水素、または炭素数1〜10のアルキル基またはアルケニル基またはアリール基またはアルキルアリール基である。
一般式(1)中、Xはヒドロキシル基、アミノ基、チオール基から選ばれる1種または2種以上からなるm個の官能基を有する分子量100万以下の直鎖または分枝鎖または環状鎖または芳香族炭化水素鎖であるスペーサーであり、Xは、前記ヒドロキシル基、アミノ基、チオール基以外の置換基を有していてもよい。
一般式(1)中、Xは好ましくはヒドロキシル基、アミノ基、チオール基から選ばれる1種または2種以上の官能基をm個有する分子量100万以下のm価の化合物の残基であって、ヒドロキシル基、アミノ基、チオール基以外の置換基を有していてもよい化合物残基である。ここで、m価の上記化合物は、m個の官能基に由来する結合を作りうることを意味する。それらは光学異性体、例えば、D−体、L−体、ラセミ体であるかは問わない。
The acidic amino acid is a monoaminodicarboxylic acid having 2 and 1 carboxyl groups and 1 amino group, respectively, in the molecule, and the amino group may be an N-methyl group or an N-ethyl group. It does not matter whether it is an optical isomer, for example, D-form, L-form, or racemate. Examples of acidic amino acids include glutamic acid, aspartic acid, lanthionine, β-methyllanthionine, cystathionine, diencholic acid, ferrinin, aminomalonic acid, β-oxyaspartic acid, α-amino-α-methylsuccinic acid, β-oxy Glutamic acid, γ-oxyglutamic acid, γ-methylglutamic acid, γ-methyleneglutamic acid, γ-methyl-γ-oxyglutamic acid, α-aminoadipic acid, α-amino-γ-oxyadipic acid, α-aminopimelic acid, α-amino -Γ-oxypimelic acid, β-aminopimelic acid, α-aminosuberic acid, α-amino sebacic acid, pantothenic acid and the like.
The n substituents Q attached to X (represented by the formula (2)) are preferable because the acidic amino acid is an L-acidic amino acid molecule because it is excellent in biodegradability.
In the general formula (2), Z is a bonding part (—O) derived from m functional groups (hydroxyl group, amino group, thiol group) substituted with X (m ≧ n and an integer of 2 to 20). -, -NR < 3 >-, -S-). Here, R 3 is hydrogen, an alkyl group having 1 to 10 carbon atoms, an alkenyl group, an aryl group, or an alkylaryl group.
In general formula (1), X is a linear or branched or cyclic chain having a molecular weight of 1 million or less and having m functional groups consisting of one or more selected from a hydroxyl group, an amino group and a thiol group. It is a spacer which is an aromatic hydrocarbon chain, and X may have a substituent other than the hydroxyl group, amino group and thiol group.
In the general formula (1), X is preferably a residue of an m-valent compound having a molecular weight of 1 million or less and having m functional groups of one kind or two or more kinds selected from a hydroxyl group, an amino group and a thiol group. , A compound residue that may have a substituent other than a hydroxyl group, an amino group, or a thiol group. Here, the m-valent compound means that a bond derived from m functional groups can be formed. It does not matter whether they are optical isomers, for example, D-form, L-form, or racemate.
このようなm価の化合物としては、例えば、セリン、トレオニン、システイン、シスチン、シスチンジスルホキシド、シスタチオニン、メチオニン、アルギニン、リジン、チロシン、ヒスチジン、トリプトファン、オキシプロリン等のアミノ酸類;
アミノエタノール、アミノプロパノール、アミノブタノール、アミノペンタノール、アミノヘキサノール、アミノプロパンジオール、アミノエチルエタノールアミン、アミノエチルアミノエタノール、アミノクレゾール、アミノナフトール、アミノナフトールスルホン酸、アミノヒドロキシ安息香酸、アミノヒドロキシブタン酸、アミノフェノール、アミノフェネチルアルコール、グルコサミン等の分子内にアミノ基とヒドロキシル基を有する化合物類;
メルカプトエタノール、メルカプトフェノール、メルカプトプロパンジオール、グルコチオース等の分子内にチオール基とヒドロキシル基を有する化合物類;
アミノチオフェノール、アミノトリアゾールチオール等の分子内にチオール基とアミノ基を有する化合物類;
が挙げられる。また、タンパク質やペプチド等、またはそれらを加水分解したもの等でも良い。
また、一般式(1)中、Xは好ましくはヒドロキシル基以外の置換基を有していてもよい分子量100万以下のm価(m≧n)のポリヒドロキシル化合物残基である。ここで、m価のポリヒドロキシル化合物は、m個のエステル結合を作り得ることを意味する。それらは光学異性体、例えば、D−体、L−体、ラセミ体であるかは問わない。
Examples of such m-valent compounds include amino acids such as serine, threonine, cysteine, cystine, cystine disulfoxide, cystathionine, methionine, arginine, lysine, tyrosine, histidine, tryptophan, and oxyproline;
Aminoethanol, aminopropanol, aminobutanol, aminopentanol, aminohexanol, aminopropanediol, aminoethylethanolamine, aminoethylaminoethanol, aminocresol, aminonaphthol, aminonaphtholsulfonic acid, aminohydroxybenzoic acid, aminohydroxybutanoic acid Compounds having an amino group and a hydroxyl group in the molecule such as aminophenol, aminophenethyl alcohol, glucosamine;
Compounds having a thiol group and a hydroxyl group in the molecule such as mercaptoethanol, mercaptophenol, mercaptopropanediol, glucothiose;
Compounds having a thiol group and an amino group in the molecule such as aminothiophenol and aminotriazole thiol;
Is mentioned. Further, proteins, peptides, etc., or those obtained by hydrolyzing them may be used.
In the general formula (1), X is preferably an m-valent (m ≧ n) polyhydroxyl compound residue having a molecular weight of 1,000,000 or less, which may have a substituent other than a hydroxyl group. Here, the m-valent polyhydroxyl compound means that m ester bonds can be formed. It does not matter whether they are optical isomers, for example, D-form, L-form, or racemate.
このようなm価のポリヒドロキシル化合物としては、例えばエチレングリコール、1,2−プロパンジオール、1,3−プロパンジオール、1,2−ブタンジオール、1,3−ブタンジオール、1,4−ブタンジオール、ペンタンジオール、1,6−ヘキサンジオール、シクロヘキサンジオール、ジメチロールシクロヘキサン、ネオペンチルグリコール、1,8−オクタンジオール、:2,2,4−トリメチル−1,3−ペンタンジオール、イソプレングリコール、3−メチル−1,5−ペンタンジオール、ソルバイト、カテコール、レゾルシン、ヒドロキノン、ビスフェノールA、ビスフェノールF、水添ビスフェノールA、水添ビスフェノールF、ダイマージオール、ジメチロールプロピオン酸、ジメチロールブタン酸、酒石酸、ジヒドロキシ酒石酸、メバロン酸、3,4−ジヒドロキシけい皮酸、3,4−ジヒドロキシヒドロけい皮酸、ヒドロキシ安息香酸、ジヒドロキシステアリン酸、ジヒドロキシフェニルアラニン等およびこれらの各異性体等の2価ヒドロキシル化合物;
グリセリン、トリオキシイソブタン、1,2,3−ブタントリオール、1,2,3−ペンタントリオール、2−メチル−1,2,3−プロパントリオール、2−メチル−2,3,4−ブタントリオール、2−エチル−1,2,3−ブタントリオール、2,3,4−ペンタントリオール、:2,3,4−ヘキサントリオール、4−プロピル−3,4,5−ヘプタントリオール、2,4−ジメチル−2,3,4−ペンタントリオール、1,2,4−ブタントリオール、1,2,4−ペンタントリオール、トリメチロールエタン、トリメチロールプロパン、ジエタノールアミン、トリエタノールアミン、トリヒドロキシステアリン酸等の3価ポリヒドロキシル化合物;
ペンタエリスリトール、エリスリトール、1,2,3,4−ペンタンテトロール、2,3,4,5−ヘキサンテトロール、1,2,4,5−ペンタンテトロール、1,3,4,5−ヘキサンテトロール、ジグリセリン、ソルビタン等の4価ポリヒドロキシル化合物; アドニトール、アラビトール、キシリトール、トリグリセリン等の5価ポリヒドロキシル化合物;
ジペンタエリスリトール、ソルビトール、マンニトール、イジトール、イノシトール、ダルシトール、タロース、アロース等の6価ポリヒドロキシル化合物;
またはこれらの脱水縮合物、ポリグリセリン等が挙げられる。
また糖類、例えば、エリスロース、スレオース、エリスルロース等のテトロース;
リボース、アラビノース、キシロース、リクソース、キシルロース、リブロース等のペントース;アロース、アルトロース、グルコース、マンノース、ギューロース、イドース、ガラクトース、タロース、フラクトース、ソルボース、プシコース、タガトース等のヘキソース等の単糖類;
マルトース、イソマルトース、セロビオース、ゲンチオビオース、メリビオース、ラクトース、ツラノース、トレハロース、サッカロース、マンニトリオース、セロトリオース、ゲンチアノース、ラフィノース、メレチトース、セロテトロース、スタキオース等のオリゴ糖類;が挙げられる。
Examples of such m-valent polyhydroxyl compounds include ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, and 1,4-butanediol. , Pentanediol, 1,6-hexanediol, cyclohexanediol, dimethylolcyclohexane, neopentyl glycol, 1,8-octanediol ,: 2,2,4-trimethyl-1,3-pentanediol, isoprene glycol, 3- Methyl-1,5-pentanediol, sorbite, catechol, resorcin, hydroquinone, bisphenol A, bisphenol F, hydrogenated bisphenol A, hydrogenated bisphenol F, dimer diol, dimethylolpropionic acid, dimethylolbutanoic acid, tartaric acid, dihydride Carboxymethyl tartaric acid, mevalonic acid, 3,4-dihydroxy cinnamic acid, 3,4-dihydroxy-hydro cinnamic acid, hydroxy benzoic acid, dihydroxy stearic acid, dihydroxyphenylalanine, and the like, and divalent hydroxyl compounds such as isomers thereof;
Glycerin, trioxyisobutane, 1,2,3-butanetriol, 1,2,3-pentanetriol, 2-methyl-1,2,3-propanetriol, 2-methyl-2,3,4-butanetriol, 2-ethyl-1,2,3-butanetriol, 2,3,4-pentanetriol: 2,3,4-hexanetriol, 4-propyl-3,4,5-heptanetriol, 2,4-dimethyl Trivalents such as -2,3,4-pentanetriol, 1,2,4-butanetriol, 1,2,4-pentanetriol, trimethylolethane, trimethylolpropane, diethanolamine, triethanolamine, trihydroxystearic acid Polyhydroxyl compounds;
Pentaerythritol, erythritol, 1,2,3,4-pentanetetrol, 2,3,4,5-hexanetetrol, 1,2,4,5-pentanetetrol, 1,3,4,5-hexane Tetravalent polyhydroxyl compounds such as tetrol, diglycerin and sorbitan; pentavalent polyhydroxyl compounds such as adonitol, arabitol, xylitol and triglycerin;
Hexavalent polyhydroxyl compounds such as dipentaerythritol, sorbitol, mannitol, iditol, inositol, dulcitol, talose, allose;
Or these dehydration condensates, polyglycerol, etc. are mentioned.
Sugars such as tetrose such as erythrose, sreose, erythrulose;
Pentose such as ribose, arabinose, xylose, lyxose, xylulose, ribulose; monosaccharides such as hexose such as allose, altrose, glucose, mannose, guylose, idose, galactose, talose, fructose, sorbose, psicose, tagatose;
And oligosaccharides such as maltose, isomaltose, cellobiose, gentiobiose, melibiose, lactose, turranose, trehalose, saccharose, mannitolose, cellotriose, gentianose, raffinose, meretitose, cellotetorose, stachyose and the like.
また、その他の糖類、例えば、ヘプトース、デオキシ糖、アミノ糖、チオ糖、セレノ糖、アルドン糖、ウロン酸、糖酸、ケトアルドン酸、アンヒドロ糖、不飽和糖、糖エステル、糖エーテル、グリコシド等の残基でもよく、デンプン、グリコーゲン、セルロース、キチン、キトサン等の多糖類またはそれらを加水分解したものでもよい。
また、一般式(1)中、Xは好ましくはアミノ基以外の置換基を有していてもよい分子量100万以下のm価のポリアミノ化合物残基である。ここで、m価のポリアミノ化合物は、m個の酸アミド結合を作り得ることを意味する。それらは光学異性体、例えば、D−体、L−体、ラセミ体であるかは問わない。
このようなm価のポリアミノ化合物としては、例えば、N,N’−ジメチルヒドラジン、エチレンジアミン、N,N’−ジメチルエチレンジアミン、ジアミノプロパン、ジアミノブタン、ジアミノペンタン、ジアミノヘキサン、ジアミノヘプタン、ジアミノオクタン、ジアミノノナン、ジアミノデカン、ジアミノドデカン、ジアミノアジピン酸、ジアミノプロパン酸、ジアミノブタン酸およびこれらの各異性体等の脂肪族ジアミン類;
ジエチレントリアミン、トリアミノヘキサン、トリアミノドデカン、1,8−ジアミノ−4−アミノメチル−オクタン、2,6−ジアミノカプリン酸−2−アミノエチルエステル、1,3,6−トリアミノヘキサン、1,6,11−トリアミノウンデカン、ジ(アミノエチル)アミンおよびこれらの各異性体等の脂肪族トリアミン類;
ジアミノシクロブタン、ジアミノシクロヘキサン、3−アミノメチル−3,5,5−トリメチルシクロヘキシルアミン、トリアミノシクロヘキサン等の脂環族ポリアミン類;
ジアミノベンゼン、ジアミノトルエン、ジアミノ安息香酸、ジアミノアントラキノン、ジアミノベンゼンスルホン酸、ジアミノ安息香酸、およびこれらの各異性体等の芳香族ポリアミン類;
ジアミノキシレン、ジ(アミノメチル)ベンゼン、ジ(アミノメチル)ピリジン、ジ(アミノメチル)ナフタレン、およびこれらの各異性体等の芳香脂肪族ポリアミン類;
ジアミノヒドロキシプロパンおよびこれらの各異性体等のヒドロキシル基が置換したポリアミン類;等が挙げられる。
In addition, other saccharides such as heptose, deoxy sugar, amino sugar, thio sugar, seleno sugar, aldone sugar, uronic acid, sugar acid, ketoaldonic acid, anhydro sugar, unsaturated sugar, sugar ester, sugar ether, glycoside, etc. It may be a residue, and may be a polysaccharide such as starch, glycogen, cellulose, chitin, or chitosan, or a hydrolyzed product thereof.
In general formula (1), X is preferably an m-valent polyamino compound residue having a molecular weight of 1,000,000 or less, which may have a substituent other than an amino group. Here, an m-valent polyamino compound means that m acid amide bonds can be formed. It does not matter whether they are optical isomers, for example, D-form, L-form, or racemate.
Examples of such m-valent polyamino compounds include N, N′-dimethylhydrazine, ethylenediamine, N, N′-dimethylethylenediamine, diaminopropane, diaminobutane, diaminopentane, diaminohexane, diaminoheptane, diaminooctane, and diaminononane. , Aliphatic diamines such as diaminodecane, diaminododecane, diaminoadipic acid, diaminopropanoic acid, diaminobutanoic acid and isomers thereof;
Diethylenetriamine, triaminohexane, triaminododecane, 1,8-diamino-4-aminomethyl-octane, 2,6-diaminocapric acid-2-aminoethyl ester, 1,3,6-triaminohexane, 1,6 , 11-triaminoundecane, aliphatic triamines such as di (aminoethyl) amine and isomers thereof;
Alicyclic polyamines such as diaminocyclobutane, diaminocyclohexane, 3-aminomethyl-3,5,5-trimethylcyclohexylamine, triaminocyclohexane;
Aromatic polyamines such as diaminobenzene, diaminotoluene, diaminobenzoic acid, diaminoanthraquinone, diaminobenzenesulfonic acid, diaminobenzoic acid, and their respective isomers;
Araliphatic polyamines such as diaminoxylene, di (aminomethyl) benzene, di (aminomethyl) pyridine, di (aminomethyl) naphthalene, and their isomers;
And polyamines substituted with hydroxyl groups such as diaminohydroxypropane and isomers thereof.
また、一般式(1)中、Xは好ましくはチオール基以外の置換基を有していてもよい分子量100万以下のm価のポリチオール化合物残基である。ここで、m価のポリチオール化合物は、m個のチオエステル結合を作り得ることを意味する。それらは光学異性体、例えば、D−体、L−体、ラセミ体であるかは問わない。
このようなm価のポリチオール化合物としては、例えば、ジチオエチレングリコール、ジチオエリトリトール、ジチオトレイトール等のジチオール化合物類等が挙げられる。
Xは上に挙げた化合物の残基の中でも、炭素数1〜40の場合が好ましく、さらに好ましくはXは炭素数1〜20の場合である。また、Xは天然に存在する型である場合の方が、生分解性に優れるという点で好ましい。
一般式(2)中、Yで示されるカルボキシル基、スルホン酸基、硫酸エステル基、リン酸エステル基およびX中に含まれ得るカルボキシル基、スルホン酸基、硫酸エステル基、リン酸エステル基等は、種々の塩基性物質との間に塩を形成し得る。
かかる塩としては、例えば、アルカリ金属塩、アルカリ土類金属塩、アンモニウム塩、有機アミン塩、塩基性アミノ酸塩、多価金属塩等が挙げられ、具体的には、ナトリウム、カリウム、リチウム等のアルカリ金属、カルシウム、マグネシウム等のアルカリ土類金属、アルミニウム、亜鉛、鉄、コバルト、チタン、ジルコニウム等の金属、アンモニア、モノエタノールアミン、ジエタノールアミン、トリエタノールアミン、トリイソプロパノールアミン等の有機アミン、アルギニン、リジン等の塩基性アミノ酸等から任意に選ばれる1種または2種以上との塩である。
In the general formula (1), X is preferably an m-valent polythiol compound residue having a molecular weight of 1,000,000 or less, which may have a substituent other than a thiol group. Here, an m-valent polythiol compound means that m thioester bonds can be formed. It does not matter whether they are optical isomers, for example, D-form, L-form, or racemate.
Examples of such m-valent polythiol compounds include dithiol compounds such as dithioethylene glycol, dithioerythritol, and dithiothreitol.
X is preferably a group having 1 to 40 carbon atoms among the residues of the compounds listed above, and more preferably X is a case having 1 to 20 carbon atoms. X is preferably a naturally occurring type from the viewpoint of excellent biodegradability.
In general formula (2), a carboxyl group, a sulfonic acid group, a sulfate ester group, a phosphate ester group represented by Y and a carboxyl group, a sulfonic acid group, a sulfate ester group, a phosphate ester group, etc. that can be contained in X are: Salts can be formed with various basic substances.
Examples of such salts include alkali metal salts, alkaline earth metal salts, ammonium salts, organic amine salts, basic amino acid salts, polyvalent metal salts, and the like. Specific examples include sodium, potassium, lithium, and the like. Alkaline metals, alkaline earth metals such as calcium and magnesium, metals such as aluminum, zinc, iron, cobalt, titanium and zirconium, organic amines such as ammonia, monoethanolamine, diethanolamine, triethanolamine and triisopropanolamine, arginine, It is a salt with one or more kinds arbitrarily selected from basic amino acids such as lysine.
このような一般式(1)で示されるアシル化合物の製造方法としては、下記一般式(3)で示されるN−アシル酸性アミノ酸無水物と分子内にヒドロキシル基、アミノ基、チオール基から選ばれる1種または2種以上のm個の官能基を有する化合物とを、水および/または水と有機溶媒との混合溶媒中で反応させることによって、またはテトラヒドロフラン、ベンゼン、トルエン、キシレン、四塩化炭素、クロロホルム、アセトン等の不活性溶媒を使用して、あるいは無溶媒で−5℃〜200℃でいずれかの融点以上の温度で混合して反応することで得ることができる。
または一般式(1)で示されるアシル化合物は、N−アシル酸性アミノ酸モノ低級エステル(例えば、メチルエステル、エチルエステル)とポリヒドロキシル化合物またはポリアミノ化合物またはポリチオール化合物、または分子内にヒドロキシル基、アミノ基、チオール基のうちいずれか2種または3種を有する化合物とをジメチルホルムアミド等の適当な溶媒中に溶解し、炭酸カリウム等の触媒を加え、減圧下に−5℃〜250℃で加熱反応させた後、反応溶媒を除去することで得ることができる。あるいは、無溶媒で加熱溶融し、水酸化ナトリウム等の触媒を加えて室温〜250℃でエステル交換反応させてアシル化合物を得ることができる。
The method for producing the acyl compound represented by the general formula (1) is selected from an N-acyl acidic amino acid anhydride represented by the following general formula (3) and a hydroxyl group, an amino group, and a thiol group in the molecule. By reacting a compound having one or more kinds of m functional groups with water and / or a mixed solvent of water and an organic solvent, or tetrahydrofuran, benzene, toluene, xylene, carbon tetrachloride, It can be obtained by reacting using an inert solvent such as chloroform or acetone, or by mixing at -5 ° C to 200 ° C at a temperature equal to or higher than any melting point without solvent.
Alternatively, the acyl compound represented by the general formula (1) includes an N-acyl acidic amino acid mono-lower ester (for example, methyl ester, ethyl ester) and a polyhydroxyl compound, a polyamino compound, or a polythiol compound, or a hydroxyl group or an amino group in the molecule. , A compound having any two or three of the thiol groups is dissolved in a suitable solvent such as dimethylformamide, a catalyst such as potassium carbonate is added, and the reaction is performed at −5 ° C. to 250 ° C. under reduced pressure. Then, it can be obtained by removing the reaction solvent. Alternatively, the acyl compound can be obtained by melting with heating without a solvent, adding a catalyst such as sodium hydroxide, and performing a transesterification reaction at room temperature to 250 ° C.
本発明のコンタクトレンズ洗浄剤の配合量は、特に制限はないが、成分(A)の多鎖多親水基型化合物含量が0.01〜5質量%とするのが好ましく、目的に応じて調節することができる。より好ましくは、組成物中において0.05〜3質量%である。多鎖多親水基型化合物含量が上記範囲より少ないと、洗浄性や装着時の目の乾燥感の防止が十分でない場合がある。また、上記範囲より多い場合には、べたつき等の感触が起こる場合がある。
本発明の好ましい態様において配合される成分(B)の保湿成分としては、分子内に2個以上の水酸基を有する前記のようなポリヒドロキシル化合物、ヒアルロン酸(ナトリウム)、コンドロイチン硫酸(ナトリウム)、デルマタン硫酸等のムコ多糖類(塩)、(水溶性)コラーゲン、エラスチン、ピロリドンカルボン酸、トリメチルグリシン、乳酸塩類、セラミド類、アロエ、アルニカ、イラクサ、イリス、ウスベニアオイ、オトギリソウ、カミツレ、サルビア、シラカバ、スギナ、セイヨウサンザシ、セイヨウノコギリソウ、タイム、ニンジン、ハマメリス、パンジー、ヒナゲシ、ラベンダー、ローズマリー、レモン、ユーカリ、ダイズ等の植物抽出エキス、ビフィズス菌等の発酵エキス等が挙げられる。これらの保湿成分は、2種以上混合して用いても良く、配合量は総量で3〜50質量%とするのが好ましい。3質量%以下では酵素の安定性効果が十分でない場合があり、50質量%以上では液の粘度が高くなりすぎる場合がある。これらの保湿性のなかでも、グリセリン、プロピレングリコール、ソルビトール、トリメチルグリシン、ピロリドンカルボン酸またはその塩が好ましい。
The blending amount of the contact lens cleaning agent of the present invention is not particularly limited, but the content of the multi-chain polyhydrophilic group compound (A) is preferably 0.01 to 5% by mass, and is adjusted according to the purpose. can do. More preferably, it is 0.05-3 mass% in a composition. If the content of the multi-chain polyhydrophilic group-type compound is less than the above range, there are cases where the washability and the prevention of dryness of the eyes at the time of wearing are not sufficient. Further, when the amount is larger than the above range, stickiness or the like may occur.
Examples of the moisturizing component (B) blended in a preferred embodiment of the present invention include polyhydroxyl compounds having two or more hydroxyl groups in the molecule, hyaluronic acid (sodium), chondroitin sulfate (sodium), dermatan Mucopolysaccharides (salts) such as sulfuric acid, (water-soluble) collagen, elastin, pyrrolidone carboxylic acid, trimethylglycine, lactates, ceramides, aloe, arnica, nettle, iris, euglena, hypericum, chamomile, salvia, birch, horsetail , Plant extracts such as hawthorn, yarrow, thyme, carrot, hamamelis, pansy, dairy, lavender, rosemary, lemon, eucalyptus and soybean, and fermented extracts such as bifidobacteria. These moisturizing components may be used in combination of two or more, and the blending amount is preferably 3 to 50% by mass in total. If it is 3% by mass or less, the stability effect of the enzyme may not be sufficient, and if it is 50% by mass or more, the viscosity of the liquid may be too high. Among these moisturizing properties, glycerin, propylene glycol, sorbitol, trimethylglycine, pyrrolidone carboxylic acid or a salt thereof is preferable.
本発明の好ましい態様において配合される成分(C)の加水分解酵素としては、タンパク質分解酵素、脂質分解酵素、糖鎖分解酵素などを用いることができる。
タンパク質分解酵素としては、タンパク質分解酵素として通常用いられるものであれば如何なるものであっても良いが、例えば、微生物由来のサブチリシンを用いたもの(ナガセケムテックス社製:登録商標「ビオプラーゼ」等)やアスペルギルス、ストレプトマイセス、バシラス等、動植物由来のトリプシン、キモトリプシン、エラスターゼ、パパイン等が好ましい。また脂質分解酵素としては、脂質分解酵素として通常用いられるものであれば如何なるものであっても良いが、例えば、リパーゼ、ホスホリパーゼ、コレステロールエステラーゼ等が好ましい。また糖鎖分解酵素としては、糖鎖分解酵素として通常用いられるものであれば如何なるものであっても良いが、例えば、α−アミラーゼ、エンドグリコシダーゼD、エンド−β−ガラクトシダーゼ、β−ガラクトシダーゼ、セルラーゼ、デキストラナーゼ等が好ましい。また、プロテアーゼ活性、アミラーゼ活性、リパーゼ活性を有するパンクレアチンのような複合酵素も用いることができる。
また、本発明の好ましい態様においては、成分(C)加水分解酵素のうち1種以上を単独でまたは混合して用いることができ、配合量は総量で0.0001〜10質量%が好ましく、さらに好ましくは0.001〜2質量%である。0.0001質量%未満では洗浄能が十分でない場合があり、10質量%より多いと目や皮膚への刺激やアレルギーを起こす場合があるなど、安全上好ましくない。
As a hydrolase of component (C) to be blended in a preferred embodiment of the present invention, a proteolytic enzyme, a lipolytic enzyme, a sugar chain degrading enzyme and the like can be used.
The proteolytic enzyme may be any one as long as it is usually used as a proteolytic enzyme. For example, a proteolytic enzyme using a subtilisin derived from a microorganism (manufactured by Nagase ChemteX Corp .: registered trademark “Bioplase”, etc.) And trypsin derived from animals and plants such as Aspergillus, Streptomyces, Bacillus, etc., chymotrypsin, elastase, papain and the like are preferable. The lipolytic enzyme may be any as long as it is usually used as a lipolytic enzyme. For example, lipase, phospholipase, cholesterol esterase and the like are preferable. The sugar chain degrading enzyme may be any sugar chain decomposing enzyme as long as it is usually used. For example, α-amylase, endoglycosidase D, endo-β-galactosidase, β-galactosidase, cellulase. Dextranase and the like are preferable. A complex enzyme such as pancreatin having protease activity, amylase activity, and lipase activity can also be used.
In a preferred embodiment of the present invention, one or more of the component (C) hydrolase can be used alone or in combination, and the blending amount is preferably 0.0001 to 10% by mass, Preferably it is 0.001-2 mass%. If it is less than 0.0001% by mass, the detergency may not be sufficient, and if it exceeds 10% by mass, it may cause irritation to the eyes and skin or may cause allergies.
本発明の好ましい態様において配合される成分(D)のホウ素化合物としては、水中における加水分解酵素の安定化効果のあるものであれば如何なるものでもよく、例えば、ホウ素、ホウ酸、ホウ砂、フェニルホウ素等が用いられる。なかでもホウ酸またはホウ素等の無機のホウ素化合物が好ましい。本発明のコンタクトレンズ洗浄剤においては、成分(D)ホウ素化合物のうち1種以上を単独でまたは混合して用いることができ、配合量は総量で0.1〜10質量%が好ましく、より好ましくは0.1〜2質量%である。0.1質量%未満では酵素の安定化効果が不十分の場合があり、また10質量%より多くてもそれ以上の効果は期待されず、沈殿等液の安定性に問題を生じる場合がある。
本発明のコンタクトレンズ洗浄剤は、塩基性物質による中和率を調整することにより好ましくはpH3〜12の広範囲のpH域で使用することができ、より好ましくは該組成物のpH5〜11の範囲で使用できる。さらに好ましくは、pH6〜8の範囲で使用できる。
本発明のコンタクトレンズ洗浄剤は通常の攪拌機、混合機、分散機等を備えた装置を用いる方法によって製造することができる。
また本発明のコンタクトレンズ洗浄剤においては、本発明の目的が損なわれない限り、用途、目的に応じ各種の基材と併用することができる。
The boron compound of component (D) to be blended in a preferred embodiment of the present invention may be any compound as long as it has a hydrolase stabilizing effect in water. For example, boron, boric acid, borax, phenyl Boron or the like is used. Among these, inorganic boron compounds such as boric acid or boron are preferable. In the contact lens cleaning agent of the present invention, one or more of the component (D) boron compounds can be used alone or in combination, and the blending amount is preferably 0.1 to 10% by mass, more preferably Is 0.1 to 2% by mass. If the amount is less than 0.1% by mass, the enzyme stabilizing effect may be insufficient, and if it exceeds 10% by mass, no further effect is expected, which may cause problems in the stability of the liquid such as precipitation. .
The contact lens cleaning agent of the present invention can be used in a wide pH range of preferably 3 to 12, more preferably in the range of pH 5 to 11 of the composition by adjusting the neutralization rate with a basic substance. Can be used in More preferably, it can be used in the range of pH 6-8.
The contact lens cleaning agent of the present invention can be produced by a method using an apparatus equipped with an ordinary stirrer, mixer, disperser and the like.
Moreover, in the contact lens cleaning agent of this invention, unless the objective of this invention is impaired, it can be used together with various base materials according to a use and the objective.
例えば、ポリビニルアルコール、ポリビニルピロリドン、カルボキシビニルポリマー等の通常知られるビニル系モノマーの(共)重合により得られるビニル系高分子が挙げられ、ここでビニル系モノマーとしては、例えば、スチレン系モノマー、ビニルエーテル系モノマー、アルキルメタアクリレート系モノマー、水酸基含有(メタ)アクリレート系モノマー、ホスホリルコリン基含有(メタ)アクリレート系モノマー、ポリアルキレングリコール(メタ)アクリレート系モノマー、含窒素モノマー、(ハロゲン置換)炭化水素系モノマー等を挙げることができる。
また、ヒドロキシプロピルセルロース、メチルセルロース、エチルセルロース、ヒドロキシプロピルメチルセルロース、カルボキシメチルセルロース、ヒドロキシエチルメチルセルロース、結晶セルロース等のセルロース系高分子、:ヒアルロン酸ナトリウム、コンドロイチン硫酸ナトリウム等の多糖類等、:ポリエチレングリコール、等の水溶性高分子;
エチレンジアミン四酢酸およびその塩類、ヒドロキシエチレンジアミン3酢酸およびその塩類、リン酸、アスコルビン酸、コハク酸、グルコン酸、ポリリン酸塩類、メタリン酸塩、ヒノキチール類などの金属イオン封鎖剤;
塩化ナトリウム、塩化カリウム、塩化マグネシウム等の無機塩化物;
アルキルトリエタノールアミン、パラベン、塩化ポリドロニウム、クロロブタノール、パラオキシ安息香酸エステル類、安息香酸およびその塩類、フェノキシエタノール、ヒノキチール、塩化ベンザルコニウム、チメロザール、グルコン酸クロルヘキシジン、ソルビン酸、ポリヘキサメチレンビグアニド等の防腐剤;
クエン酸、リンゴ酸、アジピン酸、グルタミン酸、アスパラギン酸、塩酸、酢酸、水酸化ナトリウム、リン酸塩、クエン酸塩、トリス(ヒドロキシメチル)アミノメタン等のpH調整剤;
疎水基部の炭素数8〜20の高級脂肪酸の塩である高級脂肪酸塩(石鹸);
構成アシル基としては、炭素数8〜20のもので前記したようなものが挙げられ、構成アミノ酸としては、グルタミン酸やアスパラギン酸等の前記した酸性アミノ酸類、またはグリシン、アラニン、バリン、ロイシン、イソロイシン、プロリン、メチオニン、システイン、トリプトファン、チロシン、フェニルアラニン、アスパラギン、グルタミン、セリン、トレオニン、オキシプロリン、β−アミノプロピオン酸、γ−アミノ酪酸、アントラニル酸、m−アミノ安息香酸、p−アミノ安息香酸、等のアミノ酸等が挙げられるN−アシルアミノ酸型アニオン界面活性剤;
アルキルエーテルカルボン酸塩、アミドエーテルカルボン酸塩等、アルキル硫酸エステル塩(AS)、ポリオキシエチレンアルキルエーテル硫酸エステル塩(AES)、アルキルエーテル硫酸塩、高級脂肪酸エステルの硫酸塩、高級脂肪酸アルキロールアミドの硫酸塩、硫酸化油脂、ポリオキシエチレンスチレン化フェニルエーテル硫酸塩、アルファ−オレフィンスルホン酸塩(AOS)、アルキルベンゼンスルホン酸塩、アルキルナフタレンスルホン酸塩、アルキルスルホン酸塩(SAS)、ジアルキルスルホコハク酸塩、アルファースルホン化脂肪酸塩、アルカンスルホン酸塩、高級脂肪酸エステルのスルホン酸塩、アルファースルホン化脂肪酸塩、高級脂肪酸アミドのスルホン酸塩、N−アシル−N−アルキルタウリン塩、N−アシル−N−メチルタウリン塩、アルキルリン酸塩、アルキルエーテルリン酸塩、ポリオキシエチレンアルキルエーテルリン酸塩、ポリオキシエチレンアルキルフェニルエーテルリン酸塩、ナフタリンスルフォン酸塩ホルマリン縮合物などのアニオン性界面活性剤;
アルキルベタイン類、アルキルアミドベタイン類、アルキルスルホベタイン類、イミダゾリニウムベタイン類、レシチン類などの両性界面活性剤;
ポリオキシエチレンアルキルエーテル(AE)、ポリオキシエチレンアルキルフェニルエーテル、ポリオキシエチレンポリスチリルフェニルエーテル、ポリオキシエチレンポリオキシプロピレングリコール、ポリオキシエチレンポリオキシプロピレンアルキルエーテル、ポリオキシアルキレン脂肪酸エステル、ポリオキシアルキレンソルビタン脂肪酸エステル、ポリオキシアルキレン脂肪酸アルカノールアミド、ポリオキシアルキレンアルキルグルコシド、ポリオキシアルキレン硬化ひまし油、ポリオキシアルキレンアルキルアミン、ポリオキシアルキレンアルキルフェニルエーテル、等の酸化エチレン縮合型、:多価アルコール脂肪酸部分エステル、ポリオキシエチレン多価アルコール脂肪酸部分エステル、ポリオキシエチレン脂肪酸エステル、(ポリ)グリセリン脂肪酸エステル、ポリオキシエチレン硬化ひまし油、ポリオキシエチレンアルキルアミン、トリエタノールアミン脂肪酸部分エステル、アルキルポリグルコシド、プロピレングリコール脂肪酸エステル、ソルビタン脂肪酸エステル、ショ等脂肪酸エステル等の多価アルコールエステル、:脂肪酸アルカノールアミド、糖アミンアシル化物、トリエタノールアミン脂肪酸部分エステル、脂肪酸アルキロールアミド、アルキルアミンオキサイド、等のノニオン性界面活性剤;
第1〜第3級脂肪アミン塩、塩化アルキルアンモニウム塩、テトラアルキルアンモニウム塩、トリアルキルベンジルアンモニウム塩、アルキルピリジニウム塩、アルキルヒドロキシエチルイミダゾリニウム塩、ジアルキルモルフォリニウム塩、アルキルイソキノリウム塩、ベンゼトニウム塩、ベンザルコニウム塩などのカチオン性界面活性剤;
アルギン酸ナトリウム、デンプン誘導体、トラガントゴムなどの高分子界面活性剤;
リン脂質、レシチン、ラノリン、コレステロール、サポニンなどの天然界面活性剤;等の界面活性剤が挙げられる。
Examples thereof include vinyl polymers obtained by (co) polymerization of commonly known vinyl monomers such as polyvinyl alcohol, polyvinyl pyrrolidone, and carboxyvinyl polymer. Here, examples of vinyl monomers include styrene monomers and vinyl ethers. Monomers, alkyl methacrylate monomers, hydroxyl group-containing (meth) acrylate monomers, phosphorylcholine group-containing (meth) acrylate monomers, polyalkylene glycol (meth) acrylate monomers, nitrogen-containing monomers, (halogen-substituted) hydrocarbon monomers Etc.
Cellulose polymers such as hydroxypropylcellulose, methylcellulose, ethylcellulose, hydroxypropylmethylcellulose, carboxymethylcellulose, hydroxyethylmethylcellulose, crystalline cellulose, etc .: polysaccharides such as sodium hyaluronate, sodium chondroitin sulfate, etc .: polyethylene glycol, etc. Water-soluble polymer;
Sequestering agents such as ethylenediaminetetraacetic acid and its salts, hydroxyethylenediaminetriacetic acid and its salts, phosphoric acid, ascorbic acid, succinic acid, gluconic acid, polyphosphates, metaphosphates, hinokitiles;
Inorganic chlorides such as sodium chloride, potassium chloride, magnesium chloride;
Preservation of alkyltriethanolamine, parabens, polydronium chloride, chlorobutanol, paraoxybenzoates, benzoic acid and its salts, phenoxyethanol, hinokitile, benzalkonium chloride, thimerosal, chlorhexidine gluconate, sorbic acid, polyhexamethylene biguanide, etc. Agent;
PH adjusters such as citric acid, malic acid, adipic acid, glutamic acid, aspartic acid, hydrochloric acid, acetic acid, sodium hydroxide, phosphate, citrate, tris (hydroxymethyl) aminomethane;
A higher fatty acid salt (soap) which is a salt of a higher fatty acid having 8 to 20 carbon atoms in the hydrophobic group;
Examples of the constituent acyl group include those having 8 to 20 carbon atoms as described above, and examples of the constituent amino acid include acidic amino acids such as glutamic acid and aspartic acid, or glycine, alanine, valine, leucine, and isoleucine. , Proline, methionine, cysteine, tryptophan, tyrosine, phenylalanine, asparagine, glutamine, serine, threonine, oxyproline, β-aminopropionic acid, γ-aminobutyric acid, anthranilic acid, m-aminobenzoic acid, p-aminobenzoic acid, N-acyl amino acid type anionic surfactants including amino acids such as
Alkyl ether carboxylates, amide ether carboxylates, etc., alkyl sulfate esters (AS), polyoxyethylene alkyl ether sulfate esters (AES), alkyl ether sulfates, higher fatty acid ester sulfates, higher fatty acid alkylolamides Sulfate, sulfated oil, polyoxyethylene styrenated phenyl ether sulfate, alpha-olefin sulfonate (AOS), alkylbenzene sulfonate, alkylnaphthalene sulfonate, alkyl sulfonate (SAS), dialkylsulfosuccinic acid Salts, alpha-sulfonated fatty acid salts, alkane sulfonates, sulfonates of higher fatty acid esters, alpha-sulfonated fatty acid salts, sulfonates of higher fatty acid amides, N-acyl-N-alkyltaurine salts, N-acyl Anionic surfactants such as N-methyl taurate, alkyl phosphate, alkyl ether phosphate, polyoxyethylene alkyl ether phosphate, polyoxyethylene alkyl phenyl ether phosphate, naphthalene sulfonate formalin condensate ;
Amphoteric surfactants such as alkylbetaines, alkylamidobetaines, alkylsulfobetaines, imidazolinium betaines, lecithins;
Polyoxyethylene alkyl ether (AE), polyoxyethylene alkyl phenyl ether, polyoxyethylene polystyryl phenyl ether, polyoxyethylene polyoxypropylene glycol, polyoxyethylene polyoxypropylene alkyl ether, polyoxyalkylene fatty acid ester, polyoxyalkylene Sorbitan fatty acid esters, polyoxyalkylene fatty acid alkanolamides, polyoxyalkylene alkyl glucosides, polyoxyalkylene hydrogenated castor oil, polyoxyalkylene alkyl amines, polyoxyalkylene alkyl phenyl ethers, and other ethylene oxide condensation types: polyhydric alcohol fatty acid partial esters , Polyoxyethylene polyhydric alcohol fatty acid partial ester, polyoxyethylene fatty acid ester (Poly) glycerin fatty acid ester, polyoxyethylene hydrogenated castor oil, polyoxyethylene alkylamine, triethanolamine fatty acid partial ester, alkylpolyglucoside, propylene glycol fatty acid ester, sorbitan fatty acid ester, fatty acid ester such as sho, etc. Esters, nonionic surfactants such as fatty acid alkanolamides, sugar amine acylates, triethanolamine fatty acid partial esters, fatty acid alkylolamides, alkylamine oxides;
Primary to tertiary fatty amine salts, alkylammonium chloride salts, tetraalkylammonium salts, trialkylbenzylammonium salts, alkylpyridinium salts, alkylhydroxyethylimidazolinium salts, dialkylmorpholinium salts, alkylisoquinolium salts, Cationic surfactants such as benzethonium salts and benzalkonium salts;
Polymeric surfactants such as sodium alginate, starch derivatives, tragacanth gum;
And surfactants such as phospholipids, lecithin, lanolin, cholesterol, saponins, and other natural surfactants.
以下で、本発明を実施例等を用いてさらに具体的に説明するが、本発明はこれら実施例等により何ら限定させるものではない。
本発明の実施例等で用いる評価手段などは以下の通りである。
(皮膚刺激性試験)
健常男子5人のパネラーの前腕屈曲部皮膚に、洗浄剤試料0.1gを3日間開放塗布後、皮膚刺激性の有無を評価した。判定結果は、下記の評価点の平均点が、0点以上1点未満の場合:○、1点以上2点未満の場合:△、2点以上の場合:×で示す。
判定基準と評価点数
紅斑、浮腫、水疱 (4点)
紅斑、浮腫 (3点)
紅斑 (2点)
軽微な紅斑 (1点)
無紅斑、無浮腫 (0点)
(洗浄性試験)
アルブミン0.6質量部、グロブリン0.3質量部、リゾチーム0.2質量部、ムチン0.1質量部を含む生理食塩水中で、ハードコンタクトレンズ(旭化成アイミー製;商標:アイミーEXプレミアム)を65℃で2時間浸漬処理し、レンズを汚染させた後、10分間乾燥し汚染レンズを得た。この汚染レンズを洗浄剤に入れ、室温で1時間浸漬した後、水道水で洗浄し、汚れ落ちを下記の基準で評価した。
判定結果は、下記のとおりに表した。
○ : 汚れむらまたは汚れがない場合
△ : やや汚れむらまたは汚れが残存している
× : 汚れむらまたは汚れが残存している
(装着感評価)
日常コンタクトレンズを装着している被験者について、各洗浄液にコンタクトレンズを1時間浸漬後、軽く水洗し、装着感(異物感および乾燥感)を下記評価基準に基づいて評価した。
3 : 洗浄剤を使用しない場合と比べてが非常に改善
2 : 洗浄剤を使用しない場合と比べてやや改善
1 : 洗浄剤を使用しない場合と比べて変わらないかより不快に感じられる
上記3段階評価での平均値が2.5以上のものについては○とし、1.5以上2.5未満のものについては△とし、1.5未満のものについては×として使用感を評価した。
Hereinafter, the present invention will be described more specifically using examples and the like, but the present invention is not limited to these examples and the like.
The evaluation means used in the examples of the present invention are as follows.
(Skin irritation test)
After applying 0.1 g of a detergent sample to the skin of the flexion of the forearm of 5 healthy male panelists for 3 days, the presence or absence of skin irritation was evaluated. The determination result is indicated by a case where the average score of the following evaluation points is 0 point or more and less than 1 point: ◯, when 1 point or more and less than 2 points: Δ, when 2 points or more: ×.
Judgment criteria and score Erythema, edema, blisters (4 points)
Erythema, edema (3 points)
Erythema (2 points)
Minor erythema (1 point)
No erythema, no edema (0 points)
(Detergency test)
65 hard contact lenses (manufactured by Asahi Kasei Aimee; trademark: Aimee EX Premium) in physiological saline containing 0.6 parts by mass of albumin, 0.3 parts by mass of globulin, 0.2 parts by mass of lysozyme, and 0.1 parts by mass of mucin The lens was soaked at 2 ° C. for 2 hours to contaminate the lens and then dried for 10 minutes to obtain a contaminated lens. This contaminated lens was put in a cleaning agent, immersed for 1 hour at room temperature, then washed with tap water, and the removal of dirt was evaluated according to the following criteria.
The determination result was expressed as follows.
○: Uneven dirt or no dirt △: Uneven dirt or dirt remains slightly ×: Uneven dirt or dirt remains (Evaluation of wearing feeling)
About the test subject who wears a daily contact lens, the contact lens was immersed in each cleaning solution for 1 hour and then lightly washed, and the wearing feeling (foreign material feeling and dry feeling) was evaluated based on the following evaluation criteria.
3: Very improved compared to the case where no cleaning agent is used 2: Slightly improved compared to the case where no cleaning agent is used 1: The above three steps are not changed or felt more uncomfortable than the case where no cleaning agent is used Usability was evaluated as ◯ for those having an average value of 2.5 or more in evaluation, △ for those having an average value of 1.5 or more and less than 2.5, and × for those having an average value of less than 1.5.
〔アシル化合物の製造例1〕
L−リジン塩酸塩9.1g(0.05mol)を水57gと混合した。この液を25%水酸化ナトリウム水溶液でpH範囲を10〜11に調整しながら、また反応温度を5℃に維持しながら、攪拌下にN−ラウロイル−L−グルタミン酸無水物31.1g(0.1mol)を2時間を要して添加し、反応を実施した。さらに2時間攪拌を続けた後、ターシャリーブタノールを液中濃度20質量%となるように添加した後、75%硫酸を滴下して液のpH値を2に、また液の温度を65℃に調整した。滴下終了後、攪拌を停止し、20分間65℃で静置すると有機層と水層とに分層し、これから有機層を分離した。分離した有機層にターシャリーブタノールおよび水を添加して、温度を65℃にして20分攪拌した。攪拌停止後、静置すると有機層と水層とに分層した。得られた有機層に対して、同じ水洗操作をくり返した後、得られた有機層から溶媒を除去し、水酸化ナトリウムで固形分30質量%、pH6.7(25℃)の水溶液に中和調製した後、これを乾燥して次の式(4)に示すアシル化合物を含有する組成物を得た。
〔アシル化合物の製造例2〕
製造例1において、N−ラウロイル−L−グルタミン酸無水物31.1gをN−ココイル−L−グルタミン酸無水物(0.1mol)とし、それ以外は、製造例1の方法と同じ条件で実施し、アシル化合物を含有する組成物を得た。
[Production Example 1 of acyl compound]
9.1 g (0.05 mol) of L-lysine hydrochloride was mixed with 57 g of water. While this solution was adjusted to a pH range of 10 to 11 with a 25% aqueous sodium hydroxide solution and the reaction temperature was maintained at 5 ° C., 31.1 g of N-lauroyl-L-glutamic anhydride (0. 1 mol) was added over 2 hours to carry out the reaction. After further stirring for 2 hours, tertiary butanol was added to a concentration of 20% by mass in the liquid, 75% sulfuric acid was added dropwise to bring the pH value of the liquid to 2, and the liquid temperature to 65 ° C. It was adjusted. After completion of the dropwise addition, stirring was stopped and the mixture was allowed to stand at 65 ° C. for 20 minutes, so that the organic layer and the aqueous layer were separated, and the organic layer was separated therefrom. Tertiary butanol and water were added to the separated organic layer, the temperature was raised to 65 ° C., and the mixture was stirred for 20 minutes. After the stirring was stopped, the mixture was allowed to stand to separate into an organic layer and an aqueous layer. After repeating the same washing operation with respect to the obtained organic layer, the solvent was removed from the obtained organic layer and neutralized with sodium hydroxide to an aqueous solution having a solid content of 30% by mass and a pH of 6.7 (25 ° C.). After the preparation, this was dried to obtain a composition containing an acyl compound represented by the following formula (4).
[Production Example 2 of acyl compound]
In Production Example 1, 31.1 g of N-lauroyl-L-glutamic anhydride was changed to N-cocoyl-L-glutamic anhydride (0.1 mol), and the other conditions were carried out under the same conditions as in Production Example 1. A composition containing an acyl compound was obtained.
[実施例1〜5、比較例1〜2]
表1に示す各成分を、表1に示す配合量で使用し、洗浄剤を作成した。各洗浄剤について評価した結果を表1に示す。
Each component shown in Table 1 was used in the blending amount shown in Table 1 to prepare a cleaning agent. The results of evaluation for each cleaning agent are shown in Table 1.
本発明は、コンタクトレンズの洗浄性と皮膚等への安全性に優れ、装着時の目の乾燥感や異物感を軽減できるようなコンタクトレンズ洗浄剤として好適に利用できる。 INDUSTRIAL APPLICABILITY The present invention can be suitably used as a contact lens cleaning agent that is excellent in contact lens cleaning properties and safety to the skin, and can reduce the dryness of the eyes and the feeling of foreign matter during wearing.
Claims (8)
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JP2004354845A JP2006163008A (en) | 2004-12-08 | 2004-12-08 | Contact lens cleaning agent |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2010286513A (en) * | 2009-06-09 | 2010-12-24 | Menicon Co Ltd | Eye-lens care supply and method for hydrophilizing resin base material |
EP2604298A1 (en) * | 2011-12-15 | 2013-06-19 | DEMO SA Pharmaceutical Industry | Multipurpose solutions for contact lens care comprising chamomile |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
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JPS60196722A (en) * | 1984-03-19 | 1985-10-05 | Lion Corp | Cleaner for contact lens |
JPH0451015A (en) * | 1990-06-18 | 1992-02-19 | Tome Sangyo Kk | Liquid detergent composition for contact lens and method for washing or keeping contact lens with same |
JP2001081496A (en) * | 1999-09-10 | 2001-03-27 | Nof Corp | Denatured protein remover |
WO2004020394A1 (en) * | 2002-08-27 | 2004-03-11 | Asahi Kasei Chemicals Corporation | Novel composition containing acyl group |
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Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
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JPS60196722A (en) * | 1984-03-19 | 1985-10-05 | Lion Corp | Cleaner for contact lens |
JPH0451015A (en) * | 1990-06-18 | 1992-02-19 | Tome Sangyo Kk | Liquid detergent composition for contact lens and method for washing or keeping contact lens with same |
JP2001081496A (en) * | 1999-09-10 | 2001-03-27 | Nof Corp | Denatured protein remover |
WO2004020394A1 (en) * | 2002-08-27 | 2004-03-11 | Asahi Kasei Chemicals Corporation | Novel composition containing acyl group |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2010286513A (en) * | 2009-06-09 | 2010-12-24 | Menicon Co Ltd | Eye-lens care supply and method for hydrophilizing resin base material |
EP2604298A1 (en) * | 2011-12-15 | 2013-06-19 | DEMO SA Pharmaceutical Industry | Multipurpose solutions for contact lens care comprising chamomile |
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