1233881 玖、發明說明： 【發明所屬之技術領域】 本發明係關於一種反庚 法，此種反應型染料化合物， 鏡鏡片。更特別地是，本發明 性隱形眼鏡鏡片之反應型染料 應型染料化合物可用於製作彩 性隱形眼鏡鏡片，即使經過 autoclave sterilization)處理後 且該染料也不會從鏡片中溶解 型染料化合物及其製造方 可用於製造彩色軟性隱形眼 係關於一種可共價鍵結於軟 化合物及其製造方法，此反 色的親水性（Hydrophilic)軟 多重高壓熱滅菌（Multiple ’也不會產生褪色現象，而 釋出。 【先前技術】 目前已有許多不同的製程被用於製造不同功能性之 全彩或彩色目視的鏡片。以隱形眼鏡鏡片為例，全彩隱形 鏡片不但能改變使用者虹膜的表觀顏色，並且因為其具有 色彩，因此在鏡片的貯存、消毒、或清潔容器内的澄清溶 液中’很容易能辨別鏡片所在的位置。 I k彩色1¾形眼鏡鏡片時，需加入色彩染料。通常， 色彩染料可於鏡片形成材料聚合反應（p〇lyrnerized)之前或 之後加到該鏡片中。其中一種習知方法，是在該鏡片形成 之鈾，將無機顏料（Inorganic pigment)或長鏈有機染料 (Organic dye)，溶解或散佈於單體先驅物（M〇n〇mer preCUrs〇r)或高分子基質（Polymer matrix)中。無機顏料或 長鏈有機染料稍後可於鏡片中固著，而顯露出所要的顏 色。然而，此方法並不適用於親水性（Hydrophilic)軟性隱 1233881 形眼鏡鏡片的染色，因為此種鏡片水份含量（Water content；) 很高，常常導致色料（Colorant)遷移或溶解釋出，而造成色 彩偏移。在一般常用於親水性軟性隱形眼鏡鏡片的高壓熱 滅菌（High-pressure thermal sterilization)處理過程中，此 種染料的遷移或溶解釋出現象會更加嚴重。 美國專利第4,252,421號所提出的方法，是在軟性隱 形眼鏡鏡片上，使用一種非水溶性的染料，以減輕前述染 料不良的問題。此種鏡片，係由非水溶性的肽花青 (Phthalocyanine)染料與形成該親水性鏡片的單體，經熱 硬化完成。此種肽花青染料，舉例來說，有銅肽花青（c〇pper phthalocyanine)。此肽花青染料係固著於製備完成的鏡片 中，且於一最大水份含量35.7%的環境中，仍可穩定存在。 不過，若是使用2-羥基曱基丙烯酸乙酯（2_Hydroxyethyl methacrylate, HEMA)作為親水性單體（Hydr〇philic monomer)，並且在一水份含量為40%的環境中，此非水 溶性的肽花青染料仍然會自鏡片中溶解釋出。更糟的是， 該溶解釋出的問題會隨水份含量比例上昇，進一步惡化。 使用銅肽花青顏料[顏色指數（C〇l〇r in(jex)色素藍 15(Pigment Blue 15)]以製備全彩隱形眼鏡鏡片的方法，亦 揭露於美國專利第6,149,842號。該銅肽花青色素首先散 佈於一水溶液中，該水溶液先加入聚乙烯醇（p〇lyvinyl alcoho卜PVA)作為一分散劑（Dispersing agent)，稍後與可 交聯的（Cr〇sslinkable)聚乙烯醇先驅物（pVA 口⑽㈣叫相 混合，爾後在模子内進行光聚合反應（Ph〇t〇p〇lymerized) 以形成鏡片。但此專利中，並未揭露所用染料效能的細節 1233881 資料。如前文所述，在具有大量水份含量的環境下，染料 的溶解釋出，依然是此方法可能發生的潛在問題。 美國專利第5,516,467號也揭露了類似的概念，其中 一種甍染料（Vat dye)，如色素凡藍6(Vat Biue 6)，係先轉 換成一種隱色體（Leuco compound)，並且溶解於該親水性 N，N-二曱基丙烯醯胺（N，N_Dimethyl acrylamide)單體 中，以製備一全彩單體溶液（Tintedm〇n〇mers〇luti〇n)。而 後，該溶液與其它成份在加熱環境了，進彳聚合反應以形 成鏡片。然後該鏡片再於沸水下將該溶解的隱色體轉換變 成不可溶#堯染料。雖然此種甍染料與形成鏡片的材料為 非共價鍵結，但根據報告，其亦具有優良的穩定度，而且 在沸水中歷經200小時亦不褪色。但缺點在於，若位於一 合適的驗性環境中，該固定㈣染料亦可被轉換回溶解的 隱色體’並且’若於一酸性環境中，該£染料之反應並不 均勻（Unevenly reacted)。 其它將色彩塗佈於隱形眼鏡鏡片的方法，是藉由印刷 (Print㈣或轉印（Transfer printing)的方法，塗佈於製備完 成的鏡片_L。基本上’該方法通常藉由—矽膠打印二 (SiliC〇n —μ㈣），轉印彩色溶劑型油墨（C〇loring ink口) 於該鏡片。此種轉印方沐古处# m ^ 将P方法有缺點’因為此方法不能於乾燥 鏡片表面’將色料進行—無瑕疵密排的著色。冑多不同方1233881 发明 Description of the invention: [Technical field to which the invention belongs] The present invention relates to an anti-heptane method, such a reactive dye compound, and a mirror lens. More specifically, the reactive dye-type dye compound of the contact lens of the present invention can be used to make color contact lens. Even after autoclave sterilization, the dye does not dissolve the dye compound from the lens and the dye compound. The manufacturer can be used to make colored soft contact lenses. A soft compound which can be covalently bonded to the soft compound and its manufacturing method. The reversed hydrophilic hydrophilic soft multiple autoclaving (Multiple will not cause discoloration, and [Previous technology] At present, many different processes have been used to make full-color or color vision lenses with different functionalities. Taking contact lens lenses as an example, full-color contact lenses can not only change the appearance of the user's iris Color, and because it has color, it is easy to tell where the lens is in the clear solution in the lens storage, disinfection, or cleaning container. Ik color 1¾-shaped spectacle lenses require color dyes. Generally, Color dyes can be added to the lens-forming material before or after polymerization In lenses, one of the conventional methods is to dissolve or disperse inorganic pigments (Inorganic pigments or organic dyes) in monomers (Monomer preCUrs) of uranium formed in the lenses. r) or polymer matrix. Inorganic pigments or long-chain organic dyes can be fixed in the lens later to reveal the desired color. However, this method is not suitable for hydrophilic softness. The coloration of 1233881-shaped spectacle lenses, because such lenses have high water content (Water content;), often lead to migration or dissolution of the colorant, resulting in color shift. It is commonly used in hydrophilic soft contact lenses During the process of high-pressure thermal sterilization of the lens, the migration or dissolution of this dye will be more serious. The method proposed in US Patent No. 4,252,421 is used on soft contact lens lenses. Water-insoluble dye to alleviate the problem of poor dyes. This lens is dyed with water-insoluble peptide Phthalocyanine The monomer forming the hydrophilic lens is completed by heat curing. Such peptide cyanine dyes, for example, copper peptide cyanocyanine (copper phthalocyanine). This peptide cyanine dye is fixed to the finished In lenses, it can still exist stably in an environment with a maximum moisture content of 35.7%. However, if 2-Hydroxyethyl methacrylate (HEMA) is used as the hydrophilic monomer (Hydrophilic monomer) And in an environment with a water content of 40%, the water-insoluble peptide cyanine dye will still be explained from the lens. To make matters worse, the problem explained by this solution will worsen as the proportion of water content rises. A method for preparing a full-color contact lens using a copper peptide cyanine pigment [Color Index (Pigment Blue 15)] is also disclosed in US Patent No. 6,149,842. The copper peptide The cyanine pigment was first dispersed in an aqueous solution. The aqueous solution was firstly added with polyvinyl alcohol (Pollyvinyl alcoho PVA) as a dispersing agent. Later, it was pioneered with Crosslinkable polyvinyl alcohol. The pVA is mixed in the mouth, and then photopolymerized (Photopolized) in the mold to form a lens. However, this patent does not disclose details of the efficacy of the dye used. 1233881. As described above In an environment with a large amount of water content, the dissolution of the dyes is still a potential problem that may occur with this method. US Patent No. 5,516,467 also discloses a similar concept, one of which is a Vat dye, such as a pigment Vat Biue 6 is first converted into a Leuco compound and dissolved in the hydrophilic N, N-Dimethyl acrylamide monomer to make A full-color monomer solution (Tintedm0mersomers), and then the solution and other ingredients are heated in a heated environment and polymerized to form a lens. The lens is then subjected to boiling water to dissolve the hidden Color body conversion becomes insoluble # Yao dye. Although this vat dye is non-covalently bonded to the lens forming material, it is also reported to have excellent stability and does not fade in boiling water for 200 hours. However, the disadvantage is that if it is located in a suitable test environment, the fixed vat dye can also be converted back to the dissolved leuco 'and' if in an acidic environment, the reaction of the dye is not uniform (Unevenly reacted) . Other methods of applying color to contact lens lenses are by printing (Transfer printing or Transfer printing) method, which is applied to the finished lens_L. Basically, the method is usually printed by silicone Second (SiliC〇n — μ㈣), transfer color solvent ink (Coloring ink port) to the lens. This type of transfer Fang Mugu Chu # m ^ There are disadvantages to the P method 'because this method cannot be used to dry the lens The surface of 'the toner will be - flawless closely spaced colored helmet many different parties.
法被提出以解決該問題，某些建議使用多重轉印（M _fer—ting)㈣’以塗佈雜色點於該鏡片表面某此 使用顏料/皁體懸浮物㈣㈣讓刪咖叫⑽叫塗 佈於編核具，此模具係塵印或印刷特定的形狀或間 1233881 隔，再藉由傳統的旋轉鑄模（Spillcasting)技術，形成全彩 隱形眼鏡鏡片，例如美國專利第4,640,805號所揭露者。 這些改良方法雖然可以減輕疤缺陷（Blemish defect)的現 象’但因為多使用非共價鍵結染料，於高壓熱滅菌期間， 都蒙受色素遷移的潛在風險。因此，為了去除此缺點，反 應型色彩染料即可適合此需要。因其係與該鏡片材料行共 聚合反應（C〇p〇lymerized)形成共價鍵結，在不同使用環境 下，均可避免染料從鏡片中溶解釋出。 舉例而言，美國專利第5,352,245號即揭露一種反應 型色彩染料，其係用於製備轉印油墨（Transfer printing ink)，以便彌補前述之遷移問題（Migrati0I1 shortage)。該專 利使用一種反應型色彩染料，例如：羅慕柔黑B型 (Ramazol Black B)，連同聚乙烯吡咯烷酮（p〇lyvinyl pyr〇lidone，PVP)主劑（Binder)，與一非離子界面活性劑 (Surf actant)共同混合，以製備油墨，之後再將其轉印至親 水性隱形眼鏡，以形成具有所要圖樣的全彩隱形眼鏡鏡 片。在完成後續的驗液浸入程序後，此反應型染料可與鏡 片材料形成共價鍵結。然而該全彩隱形眼鏡鏡片的效能細 郎’卻依然付之闕如並未揭露。除此外，此方法十分繁j貞， 亦具有浸透-固著（Soaking-to-fix)技術所包含的一般缺點。 許多專利，如美國專利第4,559,059號，美國專利第 4,468,229號，美國專利第4，157,892號，美國專利第 4,891，046號，美國專利第4,553,975號，美國專利第 4,929,250號，美國專利第5,292,350號，美國專利第 5,480,927號，皆提出全彩著色於該隱形眼鏡鏡片的方法， 1233881 其係藉由將染料與已成型的鏡片，一同浸透於鹼性溶液 中，以便將染料與鏡片材料形成化學鍵結。此種反應型色 彩染料’可在聚合作用步驟之前先與該鏡片形成材料混合 物（Monomer mixtures)混合，或在鏡片聚合反應 (Polymerization)步驟之後再加入該鹼性溶液中。上述專利 中除了所提出之反應型色彩染料種類與製作程序不同 外’這些專利通常均耗時甚久（Time-consuming)，且需要 多重步驟’例如中和（Neutralization)、萃取（Extraction)、 與清洗（Rrinsing)的步驟，才能著色於該隱形眼鏡鏡片。除 此外，上述專利之製程變數均必須仔細控制，以避免不均 勻刀政（Dispersion)與不均勻染色（Colorization)之發生。 有多篇專利提出更有效的鏡片染色方法，其係先藉由 將該單體或預聚物（Prep〇lymer)與該反應型色彩染料形成 共仏鍵結’稍後將官能化後（Functi〇nalized)的該預聚物， 引入鏡片模具中進行固化（Cure)。此方法可有效減輕前述 浸透-固著（S〇aking-to_fix)方法中所描述的製程問題。下述 專利，如美國專利第4,252,421號，美國專利第5,944,853 唬美國專利第5,938,795號，美國專利第5,871，675號， 美國專利第6，149,692號’美國專利第4,795,794號，與美 :專利第6，162,844號’即使用前述技術在聚合反應步驟 前，將該染料化學固著於鏡片形成材料上。這些專利間的 】主要在於反應型色彩染料與先驅物（Precursor)的種 類不同。雖然這些專利方法有所述優點，但仍存在下列缺 =^例如，繁瑣的純化（Purification)步驟，以及於週期性 门堅熱滅菌處理後產生之過早褪色的問題 1233881 fading) 〇 總結雨述專利中所揭露的方法，通常包含—或多個缺 點。這些缺點，例如’冗長的製程時間，低轉化率(Low degi^e of c〇nversi〇n)，弱鍵結染料的溶解釋出，褪色，鏡 片色調不-致，與繁項的反應或純化過程。因&，製備具 有優良著色穩定性’但卻不具前述所提缺點之彩色隱形眼 鏡鏡片所使用之染料，並以此染料製造彩色隱形眼鏡鏡片 方法’在工業上極有需求性。 【發明内容】 本發明的目的之一是提供一種反應型染·料-單體化合 物（ReacUve dye-m〇n〇mer compound)，其可用於製備彩色 鏡片，該染料-單體化合物包含至少一吸收顏色基團 absorbing moiety)與一不飽合反應型乙烯基（Unsatwated vinyl group)。該化合物具有高反應性（Reactivity)。其可藉 由一聚合反應過程，共價鍵結於該鏡片材料。 本發明的另一目的是提供一種製造反應型染料-單體 化合物的方法，該反應型染料-單體化合物可用於製備彩色 鏡片。藉由此方法，可以製得一新穎的反應型染料-單體化 合物。此製造方法間早’其所製備而得的單一官能性毕料 -單體（Mono-functional dye-monomer)化合物，具有高純度 與高反應性。 本發明的再一個目的是提供一種使用反應型染料_單 體化合物製造彩色隱形眼鏡的方法，使反應型染料著色 (Coloring agent)於一鏡片中。根據此方法，使一反應型染 10 1233881 料-單體化合物與鏡片形成材料混合，使此混合物於鏡片模 具上固化，而製備出全彩軟性隱形眼鏡鏡片。此方法不需 要繁瑣的清洗與顯影（Developing)步驟，便可獲得該染色 均勻之全彩鏡片。 本發明的又一個目的是提供一種利用反應型染料-單 體化合物所製造的彩色隱形眼鏡，此種染色鏡片具有優良 著色L疋丨生，且其於多重鬲壓熱滅菌（Multiple autoclave sterilization)處理後，不會發生溶解釋出及過早褪色的問 題（Premature fading)。這種特出的耐久性是因為該染料_ 單體化合物能與鏡片形成材料，於固化時形成共價鍵結， 而且此高分子鏈結於高溫下具有優良穩定性$ 本發明所提供的反應型染料-單體化合物可以下列化 學簡式表示，其至少包含一吸收顏色基團（c〇1〇r abs〇rbing moiety)與一不飽合反應型乙烯基：The method was proposed to solve this problem, and some suggested the use of multiple transfer (M_fer-ting) ㈣ to coat mottled dots on the lens surface. Some pigments / soap suspensions were used. Distributing to the knitting device, this mold is used to print or print a specific shape or space between 1233881 and a traditional spin casting technology to form a full-color contact lens, as disclosed in US Patent No. 4,640,805. Although these improved methods can alleviate the phenomenon of Blemish defect ', because of the use of non-covalent bonding dyes, they all suffer from the potential risk of pigment migration during autoclaving. Therefore, in order to remove this disadvantage, a reactive color dye can be adapted to this need. Because it co-polymerizes with the lens material to form a covalent bond, the dye can be prevented from dissolving in the lens under different use environments. For example, U.S. Patent No. 5,352,245 discloses a reactive color dye, which is used to prepare transfer printing inks in order to compensate for the aforementioned migration problem (Migrati0I1 shortage). This patent uses a reactive color dye, such as: Ramazol Black B, together with polyvinyl pyrrolidone (PVP) base agent (Binder), and a non-ionic surfactant (Surf Actant) are mixed together to prepare an ink, which is then transferred to a hydrophilic contact lens to form a full-color contact lens lens having a desired pattern. After completing the subsequent test solution immersion procedure, the reactive dye can form a covalent bond with the lens material. However, the effectiveness of the full-color contact lens is still unresolved. In addition, this method is very complicated and has the general shortcomings of soaking-to-fix technology. Many patents, such as US Patent No. 4,559,059, US Patent No. 4,468,229, US Patent No. 4,157,892, US Patent No. 4,891,046, US Patent No. 4,553,975, US Patent No. 4,929,250, US Patent No. 5,292,350, US Patent No. 5,480,927 proposes a method for coloring the contact lens in full color, 1233881, which is a method of immersing a dye and a formed lens in an alkaline solution so as to form a chemical bond between the dye and the lens material. Such a reactive color dye 'may be mixed with the lens forming material mixture (Monomer mixtures) before the polymerization step, or added to the alkaline solution after the lens polymerization step. In addition to the different types of reactive color dyes and production procedures mentioned above, these patents are usually time-consuming and require multiple steps, such as Neutralization, Extraction, and The step of washing (rinsing) can be colored in the contact lens. In addition, the process variables of the above patents must be carefully controlled to avoid the occurrence of uneven dispersion and colorization. A number of patents have proposed more effective lens dyeing methods by first forming a conjugated bond between the monomer or prepolymer and the reactive color dye. 'Functi The prepolymer is introduced into a lens mold and cured. This method can effectively alleviate the process problems described in the aforementioned Soaking-to_fix method. The following patents, such as U.S. Patent No. 4,252,421, U.S. Patent No. 5,944,853, U.S. Patent No. 5,938,795, U.S. Patent No. 5,871,675, U.S. Patent No. 6,149,692 'U.S. Patent No. 4,795,794, and U.S. Patent No. 6 No. 162,844 'uses the aforementioned technique to chemically fix the dye to the lens forming material before the polymerization step. The main difference between these patents lies in the different types of reactive color dyes and precursors (Precursor). Although these patented methods have the advantages described, they still have the following shortcomings: ^ For example, tedious purification steps and premature discoloration caused by periodic door heat sterilization treatment 1233881 fading) The methods disclosed in patents often include one or more disadvantages. These shortcomings, such as' lengthy process time, low conversion (Low degi ^ e of cone), explanation of the dissolution of weakly-bonded dyes, fading, inconsistent lens shades, reaction with various items or purification process. Because of &, a method for preparing colored contact lens lenses having excellent coloring stability 'but not having the aforementioned disadvantages, and a method of manufacturing colored contact lens lenses with this dye' is extremely industrially desirable. [Summary of the Invention] One of the objectives of the present invention is to provide a reactive dye-monomer compound (ReacUve dye-monomer compound), which can be used to prepare color lenses. The dye-monomer compound contains at least one An absorbing moiety) and an unsatwated vinyl group. This compound is highly reactive. It can be covalently bonded to the lens material through a polymerization process. Another object of the present invention is to provide a method for producing a reactive dye-monomer compound, which can be used for producing a color lens. By this method, a novel reactive dye-monomer compound can be obtained. The monofunctional functional dye-monomer compound prepared by this manufacturing method early has high purity and high reactivity. Another object of the present invention is to provide a method for manufacturing a colored contact lens using a reactive dye-monomer compound, so that the reactive dye is colored in a lens. According to this method, a reactive dye 10 1233881 material-monomer compound is mixed with a lens forming material, and the mixture is cured on a lens mold to prepare a full-color soft contact lens. This method does not require tedious cleaning and development steps to obtain the uniformly colored full-color lens. Another object of the present invention is to provide a colored contact lens manufactured by using a reactive dye-monomer compound. The dyeing lens has excellent coloring properties and is subjected to multiple autoclave sterilization treatment. After that, the problem of premature fading does not occur. This exceptional durability is because the dye-monomer compound can form a covalent bond with the lens-forming material upon curing, and the polymer chain has excellent stability at high temperatures. The reaction provided by the present invention Dye-monomer compounds can be represented by the following chemical formulas, which contain at least one absorbing color group (c0rr absorbing moiety) and an unsaturated reactive vinyl group:
AB 其中， A代表一不飽合反應型乙烯基；以及 B代表一吸收顏色基團，其可吸收可見光的輻射。 A可來自於親水性含乙稀基（hydrophilic vinyl)單體， 其具有可反應的羥基與不飽合乙烯基（Pendent hydr〇xyl and unsaturated vinyl group)，舉例而言，可來自丙烯酸酯 或甲基丙烯酸醋。更具體的例子可舉出2_羥基曱基丙烯酸 乙酷、丙烯酸羥乙基、甲基丙烯醯胺、丙烯酸、乙烯醇、 乙烯基砒啶、乙烯吡咯酮，或是曱基丙烯酸丙三酯。 B可來自於商業化的反應型染料，該反應型染料可為 11 1233881 水溶性並至少含有一確酸鹽基（sulfonate group)之β_硫酸 鹽基乙基石風（β-sulphatoethyl sulphone)或是其衍生物，其顏AB wherein A represents an unsaturated reactive vinyl group; and B represents a color-absorbing group which can absorb visible light radiation. A can be derived from a hydrophilic hydro vinylic monomer, which has a reactive hydroxyl group and an unsaturated vinyl group. For example, it can be derived from acrylate or methyl ester. Acrylic vinegar. More specific examples include 2-hydroxyfluorenylacrylic acid, ethylene glycol, hydroxyethyl acrylate, methacrylamide, acrylic acid, vinyl alcohol, vinylpyridine, vinylpyrrolidone, or methylglyceryl acrylate. B can be derived from commercial reactive dyes. The reactive dyes can be 11 1233881 water-soluble β-sulphatoethyl sulphone containing at least one sulfonate group or Its derivative, its face
色指數（Color Index)可為 C. I. Reactive Yellow 14 、C. I. Reactive Yellow 15、C· I· Reactive Yellow 17、C. I. Reactive Orange 7、C· I. Reactive Orange 16、C. I· Reactive Orange 72、C· I. Reactive Red 23、C· I· Reactive Red 49、c IThe color index can be CI Reactive Yellow 14, CI Reactive Yellow 15, C · I · Reactive Yellow 17, CI Reactive Orange 7, C.I. Reactive Orange 16, C.I · Reactive Orange 72, C · I . Reactive Red 23, C · I · Reactive Red 49, c I
Reactive Red 180 - C. I. Reactive Blue 19 - C. I. Reactive Blue 20，或C· I· Reactive Blue 21。上述反應型染料除了 可取自已有的商品，也可以藉由有機合成領域的習知技術 製備而得。 上述之反應型染料-單體化合物可應用於軟性隱形眼 鏡鏡片之染色，此種鏡片可為調校型（c〇rrective)與非調校 型（Non-corrective) 〇 本發明所提供的製造反應型染料_單體化合物的方 法，係藉由反應型染料與另一提供乙婦基的反應物反應， 而將-反應型乙烯基（Reactive vinyI以卿），官能化於反 應型染.料的分子結構上。使用於此方法所製造的反應型毕 料-單體化合物僅需經過簡單的純化過程，並不需mm 化（Activati〇n)步驟，即能直接用於彩色隱形眼鏡的製造。 本發明所提供的使用反應型染料_單體化合物製造彩 色隱形眼鏡鏡片的方法，其係利用_反應型染料單體化人 ^與形成鏡 材料的親水性單體進行聚合反應，; 作用將染料固著於單體中，並且不需 干 顯影步驟。同時，此方法不需在鏡 1 #的染色或 液或染料水溶液中浸透顯影上色。’後，再於鹼性溶 12 1233881 本發明所提供的利用反應型染料-單 木丁寸早體化合物所製造 的彩色隱形眼鏡，其於固化時，染料-罩 木才叶早體化合物與鏡片形 成材料形成共價鍵結，因此不會發生染料溶解釋出及過早 褪色的問豸’且此高分子鏈結於高溫下具有優良穩定性。 【實施方式】 本發明主要係以—簡單的程序，合成—反應型染料 早體化合物。為了促進染料中的^硫酸鹽基乙基碾，盥提 供乙浠基…物反應，，親水性含乙烯單體 (Hydrophilic vinyl monomer) t ^ M ^ (Hydroxyl group)^ ’合液中’並且岔封於一充滿氮氣的瓶中。在預定溫度下反 應-段時間，此預定溫度可為室溫至5〇。。，反應時間較 佳者為12至24小時。由HPLC的結果顯示，此方法可得 ^目當高產率的產品。當然’合成反應時所使用的溫度及 才間係取决於製備染料_單體化合物時所使用的反應物。 適合用於上述反應的商業化反應型染料，可列舉出含 有夂溶H h g文鹽基（suIf〇nate gr〇Up)之不同取代型式的卜 應’因此使用-鹼性物質(base)。另外，為了避免在合成 期間’乙烯基(Vinyl groups)呈現非所要的過早反應 (^mature reaction)，因此，也使用聚合反應抑制劑 (P〇iymerization inhibitor)。其合成方式概述如下，先將 反應型染料以一預定量的鹼鹽基，在水溶液中加以活化， 此活化步驟的較佳溫度A 3…，反應時間較佳 者為〇.’5 i 4小時。然後，將預定量的提供乙烯基的反應 物以及聚合反應抑制劑加入已活化之反應型染料反應物 13 1233881 硫酸鹽基乙基颯（β-sulphatoethyl sulphone)，此種反應型 染料之顏色指數可列舉出，但不限於，c. L Reactive Yell〇wReactive Red 180-C. I. Reactive Blue 19-C. I. Reactive Blue 20, or C. I. Reactive Blue 21. In addition to the above-mentioned reactive dyes, they can be obtained from existing commercial products, or they can be prepared by conventional techniques in the field of organic synthesis. The above-mentioned reactive dye-monomer compounds can be used for dyeing soft contact lens lenses. Such lenses can be adjusted and non-corrected. Manufacturing reactions provided by the present invention Dye-monomer compound method, by reacting a reactive dye with another reactant that provides ethynyl, functionalizing a reactive dye (Reactive vinyI) to a reactive dye. Molecular structure. The reactive base-monomer compound produced by this method can be directly used in the manufacture of color contact lenses only after undergoing a simple purification process and without the need for an activation step. The present invention provides a method for producing a color contact lens lens using a reactive dye _ monomer compound, which uses _ reactive dye to singulate a human ^ and polymerize a hydrophilic monomer forming a lens material to perform a polymerization reaction; It is fixed in the monomer and does not require a dry development step. At the same time, this method does not need to be immersed in the dyeing or liquid or dye aqueous solution of the mirror 1 # to develop the color. 'Then, it is dissolved in alkaline 12 1233881. The colored contact lens manufactured by using the reactive dye-monocotine early body compound provided by the present invention, when cured, the dye-cover wood leaf early body compound and lens The forming material forms a covalent bond, so there is no problem of dye dissolution and premature discoloration, and the polymer chain has excellent stability at high temperatures. [Embodiment] The present invention mainly uses a simple procedure to synthesize a reactive early dye compound. In order to promote the ^ sulfate ethyl group in dyes, the acetyl group reaction is provided. Hydrophilic vinyl monomer t ^ M ^ (Hydroxyl group) ^ 'in the liquid' and the fork Sealed in a nitrogen filled bottle. The reaction is performed at a predetermined temperature for a period of time, and the predetermined temperature may be from room temperature to 50 °. . The better response time is 12 to 24 hours. The results of HPLC show that this method can obtain high yield products. Of course, the temperature and time used for the 'synthesis reaction depends on the reactants used in the preparation of the dye-monomer compound. Commercially-available reactive dyes suitable for the above-mentioned reactions include, for example, a base containing a different substitution type containing a soluble H h g salt (suIfOnate grOUp). In addition, in order to prevent the 'vinyl groups' from exhibiting an undesired premature reaction during the synthesis, a polymerization inhibitor is also used. The synthesis method is summarized as follows. The reactive dye is first activated in an aqueous solution with a predetermined amount of a base salt. The preferred temperature for this activation step is A 3 ..., and the preferred reaction time is 0.5 '4 hours. . Then, a predetermined amount of a reactant providing a vinyl group and a polymerization inhibitor are added to the activated reactive dye reactant 13 1233881 β-sulphatoethyl sulphone. The color index of this reactive dye can be List, but not limited to, c. L Reactive Yell〇w
14、C. I. Reactive Yellow 15、C· I· Reactive Yellow 17、 C· I· Reactive Orange 7、C· I. Reactive Orange 16、C. I· Reactive Orange 72、C· I· Reactive Red 23、C· I· Reactive Red 49、C· I. Reactive Red 180、C· I· Reactive Blue 19 (RB 19)、C· I. Reactive Blue 20,以及 C· I· Reactive Blue 21 (RB 21)。這些反應型染料可以取自已有的商品，也可以藉由有 機合成領域的習知技術製備而得。 製備本發明反應型染料-早體化合物所使用的提供乙 烯基的反應物之結構中，應包括羥基（或胺基）及一乙稀基 (Vinyl group)，此提供乙烯基的反應物最好為一種親水性 含乙稀基（Hydrophilic vinylic)反應物。適合的提供乙稀基 的反應物為含有乙烯基親水性反應物之共聚合單體 (Comonomers)，其可列舉出，但不限於下列化合物：2_羥 基曱基丙烯酸乙酯（2-Hhydroxyethyl methacrylate， HEMA) ’丙稀酸經乙基酉旨（Hydroxylethyl acrylate)，甲基 丙烯醯胺（Methacrylamide)，丙烯酸（Acrylic acid)，乙烯醇 (Vinyl alcohol)，乙烯基砒啶（vinyl pyridine)，乙烯吡咯酮 (N-Vinylpyrrolidone) ^ 曱基丙烯酸丙三酯（Glocer〇i methacrylate)，與諸如此類的材料。 為了促進反應所使用的鹼性物質可列舉為氨水 (Ammonia)，三乙基胺（Tdethyl amine)，鹼金屬氫氧化物 (Alkaline metal hydroxide)(如氫氧化納（s〇dium hydroxide))，與驗金屬（Alkaline metal)鹽類（如碳酸氫鈉 14 1233881 (Sodium bicarbonate))。其作用係先將反應型染料進行活化 反應，使β-硫酸鹽基乙基砜轉換成具有反應性的乙烯砜 (Vinylsulf〇ne)。鹼性物質添加的莫耳當量，最好大於該反 應型染料反應物加入的莫耳當量，以便增進該反應的效率 與產率。通常，該驗性物質對該反應型染料的莫耳比例， 最好介於1:1到5 :1間。但是所使用鹼性物質的實際量， 將與該鹼性物質的強度有十分密切的關係。 於前述反應中’一分子的反應型染料係與一分子的含 乙烯單體（Vinylic m〇nomer)(提供乙烯基的反應物）鍵結， 該鍵結係藉由反應型染料上經轉換之反應性乙烯礙基與 含乙烯單體上的羥基（Hydroxyl group)反應。因此，該反應 型染料對含乙烯單體的莫耳比例，最好介於1:1到1:5間， 以便增進該反應的效率與反應率。 上述反應中’聚合反應抑制劑（P〇lymerizati〇n inhibitor)的添加，是為了避免在合成期間，乙烯基（vinyl groups)呈現非所要的過早反應（prernature reaction)。該聚 合反應抑制劑可選自下列化合物中至少其中之一，對苯二 酚（Hydroquinone)，甲基對苯二酚（Methyl hydroquinone) ’ 甲基對苯二酚醚（Hydroquinone monomethyl ether)，兒茶酚（Catechol).，以及五倍子酚 (Pyrogallol)。聚合反應抑制劑的加入量，以含不飽和乙烯 基之反應物（Unsaturated vinylic reactant)的重量為計算基 準，為其百分之0.02%到6%之間。 於此合成反應中，其反應條件將依據所選定之反應型 染料與提供乙烯基的反應物而決定，雖然許多染料輔助化 15 1233881 學藥品，例如，分散劑（Dispersant)，鹽類（Salt)，濕潤劑 (Wetting agent)，固著劑（Fixing agent)等等，常用於漂染 製程，但是於本發明之反應型染料-單體（Dye_m〇n〇ma)化 合物製程中，並不需要添加這些漂染輔助品。 一但完成上述的合成反應，其中不需要的副產物、未 反應的反應物，以及水份，可藉由習知方法，輕易地與染 料-單體化合物產物分離。此處所指的習知方法可為晶析， 萃取，離心，過濾等等方法。依據此方法製備的反應型染 料-單體化合物，並且依照上述分離方法反覆操作後，再經 南效能液相層析法（HPLC)的分析，至少具有85%的純度。 右此反應型染料-單體化合物之純度大於8〇咯以上，即可使 用於製造染色隱形眼鏡鏡片，不需更進一步的純化。 在上述反應中，需注意的是，所選的反應型染料與提 供乙烯基的反應物（例如，親水性乙烯（Hydr〇phiHc vinyl) 反應物），應在水溶液中充份溶解。於該反應前後，兩種反 應物均應形成一均質水溶液。 此外，本發明所提供的使用染料—單體化合物製造彩色 隱形眼鏡鏡片的方法，其係在鏡片形成材料進行聚合反應 m ’將依妝上述方法所製備而得的反應型染料-單體化合 物，注入於鏡片形成材料中，然後聚合而成。該反應型染 料-單體化合物上提供可供反應接枝的乙烯基（vinylic groups)，其可與鏡片形成材料上的乙烯基（vinyHc groups)，進行光起始自由基聚合反應（ph〇t(Mnitiated radical polymerization)。其中，該鏡片形成材料可為輕 基曱基丙烯酸乙酯（HEMA>。 16 1233881 於此反應中，染料-單體化合物之加入量，係依據該鏡 片的配方所要求的色調與顏色，以該鏡片形成材料重量計 算，最好為其0.01%到0.25%之間。重要的是，於固化前 或固化後，該染料-單體化合物應完全均勻地溶於鏡片形成 材料中，以避免鏡片缺陷（Lens defects)，例如：鏡片色調不 均勻，或不同批號鏡片色調不一致之缺點。 依據本發明所形成的彩色隱形目艮鏡鏡片，於高壓熱;咸 菌處理的反覆測試後，具有優良的穩定性。 以下以具體實施例更進一步說明本發明，以下實施例 係用以闡明本發明，而非用以限制本發明之範圍。任何爛 熟有機合成技術者，均可在不脫離本創作的精神及觀點 下，進行部分修改及變更，凡依本創作申請專利範圍所做 之均等變化及修飾，皆屬本發明申請專利之涵蓋範圍。 以反應性染料RB 19合成反應型染料-單體化 合物1 人將25g的RB 19、2g氫氧化鈉，以及5〇〇g蒸餾水的 混合物，在一 i公升的圓底燒瓶中，均勻攪拌1〇分鐘。 此合均勻後，將溫度升高至40°C維持1小時。接著，將 8g HEMA以及〇.〇2g的對苯二酚加入前述溶液中並均勻攪 拌。將此溶液在3〇。(：的油浴中反應24小時。之後，冷卻 至室^，將產物進行真空乾燥，再進行純化步驟。此純化 y驟疋以95%的酒精進行萃取，經過濾以及真空乾燥，並 重複貫知別述純化步驟以得到所需的純度。經此合成反應 所產生之產物為約llg的暗色粉末。HpLc的分析結果指 17 1233881 出經純化後產物的純度接近87%。 1麵例2以反應性染料RB 21合成反應型染料-單體化 合物 將25g的RB 21、2g氫氧化納，以及5〇〇g蒸顧水的 混合物，在一 1公升的圓底燒瓶中，均勻攪拌1〇分鐘。 混合均勻後’將溫度升南至4 0。C維持1小時。接著，將 8g的HEMA以及〇.〇2g的對苯二酚加入前述溶液中並均 勻攪拌，將此溶液在30°C的油浴中反應24小時。之後， 冷卻至室溫，將產物進行真空乾燥，再進行純化步驟。此 純化步驟是依照實施例1中的純化步驟，進行萃取、過遽， 以及真空乾燥，並重複實施以得到所需的純度。經此合成 反應所產生之產物為約10g的暗色粉末。HPLC的分析結 果指出經純化後產物的純度接近9〇%。 t施例3以C· L Reactive Yellow 15合成反應型染料_ 單體化合物 將 25g 反應性染料 c· I· Reactive Yellow 15、5g 碳酸 鈉，以及500g蒸餾水的混合物，在一 i公升的圓底燒瓶 中，均勻攪拌10分鐘。混合均勻後，將溫度升高至4〇c>C 維持1小時。接著，將8gHEMA以及〇 〇2g的對苯二酚加 入前述溶液中並均勻攪拌。將此溶液在3〇cc的油浴中反 應24小時。之後，冷卻至室溫，將產物進行真空乾燥， 再進行純化步驟。此純化步驟是依照實施例i中的純化步 18 1233881 驟，進行萃取、過濾，以及真空乾燥，並重複實施以得到 所需的純度。經此合成反應所產生之產物為約8g的黃色 粉末。HPLC的分析結果指出經純化後產物的純度接近 92% 〇 宽施例4以C· I. Reactive Red 180合成反應型染料-單 體化合物 將 25g C. I. Reactive Redl80、5g 碳酸鈉，以及 500g 蒸餾水的混合物，在一 1公升的圓底燒瓶中，均勻攪拌1〇 分鐘。混合均勻後，將溫度升高至40°C維持1小時。接 著，將8g HEMA以及0.02g的對苯二酚加入前述溶液中並 均勻攪拌。將此溶液在30°C的油浴中反應24小時。之後， 冷卻至室溫’將產物進行真空乾燥，再進行純化步驟。此 純化步驟是依照實施例1中的純化步驟，進行萃取、過濾， 以及真空乾燥’並重複實施以得到所需的純度。經此合成 反應所產生之產物為約7g的黃色粉末。HPLC的分析結 果指出經純化後產物的純度接近9 3 %。 實遮羞5彩色軟性隱形眼鏡鏡片的製備 以下列舉製備彩色軟性隱形眼鏡鏡片的基本配方如 後：55%的水份含量，100份的2-羥基甲基丙烯酸乙酯 (HEMA)，15 伤的乙稀 η比嘻 _ (N-Vinyi pyrr〇iid〇ne)，〇·2 份 2-氣塞吨酮（2-Chl〇r〇thioxanthone，光起始劑（Photo initiator) )，1·2 份曱基壓克力酸（Methacrylic acid)， 份的乙一醇一甲基丙稀酸酯（Ethylene glycol 19 1233881 dimethacrylate)交聯劑（Cirosslinker)，0.04 份的染料-單 體化合物（如實施例14所製備者），與100份的丙三醇 (Glycerin) ° 上述配方於超音波槽中，經充份混合以及過濾後，分 別置於聚笨乙稀（P〇lyStyreiie)的鏡片模具中，在攝氏60度 下’由一 250瓦特（Watt)的紫外光燈（UV lamp)，以波長為 300〜410奈米（nm)的紫外光，照射15分鐘進行固化，該總 累積光能量為1900毫焦耳/平方公分（mJ/cm2)。固化後， 從板具中取出鏡片，在8〇〇C的熱水中清洗2〇分鐘，以移 去不反應的稀釋液丙三醇與未反應的殘餘組成成份。接著 於25°C浸入標準食鹽水溶液水合（Hydrate)24小時。 經上述方法所合成之鏡片，於高壓熱滅菌處理前後，14.CI Reactive Yellow 15, C.I.Reactive Yellow 17, C.I.Reactive Orange 7, C.I. Reactive Orange 16, C.I.Reactive Orange 72, C.I.Reactive Red 23, C.I. Reactive Red 49, C. I. Reactive Red 180, C. I. Reactive Blue 19 (RB 19), C. I. Reactive Blue 20, and C. I. Reactive Blue 21 (RB 21). These reactive dyes can be obtained from existing commercial products or can be prepared by conventional techniques in the field of organic synthesis. The structure of the vinyl-providing reactant used to prepare the reactive dye-early compound of the present invention should include a hydroxyl group (or an amine group) and a vinyl group (Vinyl group). It is a hydrophilic Hydrophilic vinylic reactant. Suitable reactants for providing ethylene groups are comonomers containing vinyl hydrophilic reactants, which can be exemplified, but not limited to the following compounds: 2-Hhydroxyethyl methacrylate , HEMA) 'Acrylic acid via Hydroxylethyl acrylate, Methacrylamide, Acrylic acid, Vinyl alcohol, Vinyl pyridine, Vinyl pyrrole N-Vinylpyrrolidone ^ Gloceroi methacrylate, and the like. The alkaline substances used to promote the reaction can be exemplified by ammonia (Ammonia), triethylamine (Tdethyl amine), alkali metal hydroxide (Alkaline metal hydroxide) (such as sodium hydroxide), and Alkaline metal salts (such as sodium bicarbonate 14 1233881 (Sodium bicarbonate)). Its role is to first activate the reactive dye to convert β-sulfate ethyl sulfone into reactive vinyl sulfone (Vinylsulfone). The molar equivalent added by the basic substance is preferably larger than the molar equivalent added by the reactive dye reactant in order to improve the efficiency and yield of the reaction. Generally, the molar ratio of the test substance to the reactive dye is preferably between 1: 1 and 5: 1. However, the actual amount of alkaline substance used will be very closely related to the strength of the alkaline substance. In the aforementioned reaction, one molecule of the reactive dye system is bonded to one molecule of a vinyl monomer (a vinyl reactant), and the bond system is converted by a reactive dye The reactive ethylene hindering group reacts with a hydroxyl group on a vinyl-containing monomer. Therefore, the molar ratio of the reactive dye to the ethylene-containing monomer is preferably between 1: 1 and 1: 5 in order to improve the efficiency and reaction rate of the reaction. The addition of a 'Polymerization inhibitor' in the above reaction is to prevent vinyl groups from exhibiting an unwanted premature reaction during synthesis. The polymerization inhibitor may be selected from at least one of the following compounds: hydroquinone, methyl hydroquinone 'methyl hydroquinone monomethyl ether, catechin Catechol., And Pyrogallol. The polymerization inhibitor is added in an amount based on the weight of the unsaturated vinylic reactant, which is between 0.02% and 6%. In this synthetic reaction, the reaction conditions will be determined according to the selected reactive dyes and reactants that provide vinyl groups, although many dyes assist the chemical 15 1233881 medicines, such as dispersants, salts , Wetting agent, fixing agent, etc., are often used in the bleaching process, but in the reactive dye-monomer (Dye_monam) compound process of the present invention, these do not need to be added Dyeing aids. Once the above synthesis reaction is completed, unwanted by-products, unreacted reactants, and moisture can be easily separated from the dye-monomer compound product by conventional methods. The conventional methods referred to herein may be crystallization, extraction, centrifugation, filtration, and the like. The reactive dye-monomer compound prepared according to this method, after repeated operations in accordance with the above separation method, and then analyzed by Southern Performance Liquid Chromatography (HPLC), has a purity of at least 85%. Right, the purity of this reactive dye-monomer compound is more than 800, which can be used to make tinted contact lens lenses without further purification. In the above reaction, it should be noted that the reactive dye selected and the reactant providing the vinyl group (for example, HydrophiHc vinyl reactant) should be sufficiently dissolved in the aqueous solution. Before and after the reaction, both reactants should form a homogeneous aqueous solution. In addition, the method for manufacturing a color contact lens using a dye-monomer compound provided in the present invention is a reactive dye-monomer compound prepared by polymerizing the lens forming material m ′ according to the method described above, It is injected into a lens forming material and polymerized. Vinyl groups available for reactive grafting are provided on the reactive dye-monomer compound, which can perform photo-initiated radical polymerization with the vinyl groups on the lens forming material (phOt (Mnitiated radical polymerization). Among them, the lens-forming material may be light-based fluorenyl ethyl acrylate (HEMA). 16 1233881 In this reaction, the amount of dye-monomer compound added is based on the requirements of the lens formula The hue and color are preferably 0.01% to 0.25% based on the weight of the lens forming material. It is important that the dye-monomer compound is completely and uniformly dissolved in the lens forming material before or after curing. In order to avoid lens defects, for example, the disadvantages of uneven lens hue or inconsistent hue of different batches of lenses. The color invisible eyepiece lens formed according to the present invention is subjected to high pressure heat; repeated tests of salt bacteria treatment After that, it has excellent stability. The following examples further illustrate the present invention. The following examples are intended to illustrate the present invention, but not to limit it. The scope of the invention. Anyone skilled in organic synthesis technology can make some modifications and changes without departing from the spirit and perspective of this creation. Any equivalent changes and modifications made in accordance with the scope of the patent application for this creation belong to this The scope of patent application for invention. Synthesis of reactive dye-monomer compound from reactive dye RB 19 1 A mixture of 25 g of RB 19, 2 g of sodium hydroxide, and 500 g of distilled water was used in a 1-liter round bottom. In the flask, stir uniformly for 10 minutes. After the mixture was uniform, the temperature was raised to 40 ° C and maintained for 1 hour. Next, 8 g of HEMA and 0.02 g of hydroquinone were added to the aforementioned solution and stirred uniformly. This solution was reacted in an oil bath for 30 hours. After that, it was cooled to room ^, and the product was dried under vacuum, followed by a purification step. This purification step was extracted with 95% alcohol, filtered and Dry under vacuum, and repeat the purification steps described above to obtain the desired purity. The product produced by this synthesis reaction is about llg of dark powder. The analysis result of HpLc refers to 17 1233881 The degree is close to 87%. Example 2 Synthesis of a reactive dye-monomer compound using reactive dye RB 21 A mixture of 25 g of RB 21, 2 g of sodium hydroxide, and 500 g of distilled water was added in a 1 liter of In a round-bottomed flask, stir uniformly for 10 minutes. After mixing well, the temperature was raised to 40 ° C. for 1 hour. Then, 8 g of HEMA and 0.02 g of hydroquinone were added to the solution and homogenized. After stirring, the solution was reacted in an oil bath at 30 ° C. for 24 hours. After that, it was cooled to room temperature, the product was dried under vacuum, and then the purification step was performed. This purification step is performed in accordance with the purification step in Example 1, extraction, percolation, and vacuum drying are performed repeatedly to obtain the desired purity. The product produced by this synthesis reaction was about 10 g of dark powder. HPLC analysis indicated that the purity of the product after purification was close to 90%. t Example 3 Synthesis of Reactive Dyes with C · L Reactive Yellow 15_ Monomer Compound A mixture of 25 g of reactive dye c · I · Reactive Yellow 15, 5 g of sodium carbonate, and 500 g of distilled water was placed in a 1-liter round-bottomed flask. Medium, stir evenly for 10 minutes. After mixing well, the temperature was raised to 40 ° C for 1 hour. Next, 8 g of HEMA and 0.02 g of hydroquinone were added to the aforementioned solution and stirred uniformly. This solution was reacted in a 30 cc oil bath for 24 hours. After that, it was cooled to room temperature, the product was dried under vacuum, and then the purification step was performed. This purification step is performed in accordance with the purification step 18 1233881 in Example i, extraction, filtration, and vacuum drying are performed, and repeatedly performed to obtain the desired purity. The product produced by this synthesis reaction was about 8 g of a yellow powder. The HPLC analysis indicated that the purity of the purified product was close to 92%. Example 4 A reactive dye-monomer compound was synthesized with C. I. Reactive Red 180. A mixture of 25 g of CI Reactive Red 180, 5 g of sodium carbonate, and 500 g of distilled water was used. In a 1-liter round bottom flask, stir uniformly for 10 minutes. After mixing well, raise the temperature to 40 ° C for 1 hour. Next, 8 g of HEMA and 0.02 g of hydroquinone were added to the aforementioned solution and stirred uniformly. This solution was reacted in an oil bath at 30 ° C for 24 hours. After that, the product was cooled to room temperature ', the product was dried under vacuum, and then the purification step was performed. This purification step is performed in accordance with the purification step in Example 1, followed by extraction, filtration, and vacuum drying 'and repeated implementation to obtain the desired purity. The product produced by this synthesis reaction was about 7 g of a yellow powder. HPLC analysis indicated that the purity of the purified product was close to 93%. The preparation of 5 color soft contact lens lenses is listed below. The basic formula for making color soft contact lens lenses is as follows: 55% water content, 100 parts of 2-hydroxyethyl methacrylate (HEMA), 15 wounds. Dilute η (N-Vinyi pyrroiidione), 0.2 parts 2-Chlorothioxanthone (Photo initiator), 1.2 parts 曱Methacrylic acid, parts of Ethylene glycol 19 1233881 dimethacrylate crosslinker (Cirosslinker), 0.04 parts of dye-monomer compound (as prepared in Example 14 (1), with 100 parts of glycerin ° The above formula is in an ultrasonic tank, after being fully mixed and filtered, placed in a lens mold of PolyStyreiie, at 60 ° C At a temperature of '250 Watt (UV), a UV lamp with a wavelength of 300 to 410 nanometers (nm) is irradiated for 15 minutes to cure, and the total accumulated light energy is 1900 millijoules / Square centimeter (mJ / cm2). After curing, the lens was removed from the board and washed in hot water at 800 ° C for 20 minutes to remove the unreacted diluent glycerol and unreacted residual constituents. It was then immersed in a standard saline solution for 25 hours at 25 ° C. Before and after autoclaving the lenses synthesized by the above method,
乂伯金艾碼 UV-VIS 8453 光譜儀（perkin-Elmer UV-VIS 8453 Spectrophotometer)分析其 uv/vis 光譜。該鏡片的 群斤广光譜係以1奈米的解析度，從190掃描㈣1100奈 只斤得月;I述所得之鏡片，經過高壓熱滅菌處理，此處理 係於2大氣壓，12rc下㈣’一個高塵熱滅菌處理循環 耗時約30分鐘。此彩色軟式隱形眼鏡鏡片的顏色堅牢产 高壓熱滅菌處理循環後，進行評估，該測： L鏡片的抗張強度（Tensile st㈣gth)，係以 ㈣叫拉力試驗機量測，其應變率（strain崎）為50員 /每分釦（mm/min )。具有 ‘”、 “ 而小狀與尺寸大小的拉力試片 20 1233881 係自固化完成的鏡片平軋(Die_cut)出’並量測該樣品的橫 截面積，測試所得該抗張強度與該變形率（strain)，結果表 列於表1。 at 表 本發明製得之彩色軟式隱形眼鏡鏡片的性質 選用之染料-單體 化合物 含水量 (%) 鏡片直徑 (mm)# 抗張強度 (Kg/cm2)* 拉伸率 (%) 著色穩定性+ 實施例1 ——----- 實施例2 55·1 (〇·9)$ 54.6 (0.8) 14.1 14.0 2.1 2.2 120±12 118±10 穩定 ' --- —一· 一 穩定 實施例3 54.8 (0.7) 14.0 2.1 121+13 穩定 實施例4 54.3 (0.9) 14.1 2.1 122+12 穩定 控制組(不添加染 料單體化合物） $ / \.说汾 v 55.2 (0.7) 14.1 2.2 126±11 mm ° :鏡片直徑的99%的信賴區間小於±0.2 +抗張強度的標準差小於0.2 Kg/cm2。 +穩定··在高壓熱滅菌處理循環之後，所著染料無顯著褪色 或移出。 21 1233881Perkin-Elmer UV-VIS 8453 Spectrophotometer analyzes its UV / VIS spectrum. The wide-spectrum spectrum of the lens is scanned with a resolution of 1 nanometer from 190 to 1100 nanograms; the lens obtained in paragraph I is subjected to autoclaving, which is performed at 2 atmospheres and 12 rc. The high dust heat sterilization cycle takes about 30 minutes. The color of this colored soft contact lens is evaluated after the autoclave sterilization cycle. The test: The tensile strength of the L lens (Tensile st㈣gth) is measured with a howling tensile tester, and its strain rate (strain ) Is 50 deductions per minute (mm / min). There are "", "and small and sized tensile test pieces 20 1233881 are self-curing completed lens (Die_cut) and the cross-sectional area of the sample is measured. The tensile strength and the deformation rate obtained by the test (Strain), the results are listed in Table 1. at Table shows the properties of the colored soft contact lenses produced by the present invention. The dye-monomer compound moisture content (%) selected. Lens diameter (mm) # Tensile strength (Kg / cm2) * Elongation (%) Coloring stability + Example 1 ------------ Example 2 55 · 1 (0 · 9) $ 54.6 (0.8) 14.1 14.0 2.1 2.2 120 ± 12 118 ± 10 Stable '--- --- Stable Example 3 54.8 (0.7) 14.0 2.1 121 + 13 Stability example 4 54.3 (0.9) 14.1 2.1 122 + 12 Stability control group (without dye monomer compound added) $ / \. Saifen v 55.2 (0.7) 14.1 2.2 126 ± 11 mm °: 99% confidence interval of lens diameter is less than ± 0.2 + standard deviation of tensile strength is less than 0.2 Kg / cm2. + Stable ... No significant discoloration or removal of the dye after the autoclaving cycle. 21 1233881