CN106800626A - 硅水胶组合物及以该组合物制造的硅水胶镜片 - Google Patents
硅水胶组合物及以该组合物制造的硅水胶镜片 Download PDFInfo
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- CN106800626A CN106800626A CN201710070150.3A CN201710070150A CN106800626A CN 106800626 A CN106800626 A CN 106800626A CN 201710070150 A CN201710070150 A CN 201710070150A CN 106800626 A CN106800626 A CN 106800626A
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- XJKVPKYVPCWHFO-UHFFFAOYSA-N silicon;hydrate Chemical compound O.[Si] XJKVPKYVPCWHFO-UHFFFAOYSA-N 0.000 description 1
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/068—Polysiloxanes
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/041—Lenses
- G02B1/043—Contact lenses
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F226/06—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
- C08F226/10—N-Vinyl-pyrrolidone
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
- C08F230/08—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/61—Polysiloxanes
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/81—Unsaturated isocyanates or isothiocyanates
- C08G18/8108—Unsaturated isocyanates or isothiocyanates having only one isocyanate or isothiocyanate group
- C08G18/8116—Unsaturated isocyanates or isothiocyanates having only one isocyanate or isothiocyanate group esters of acrylic or alkylacrylic acid having only one isocyanate or isothiocyanate group
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Abstract
本发明公开了一种硅水胶组合物及以该组合物制造的硅水胶镜片,硅水胶组合物,其组成包含硅高聚合物、含羟基的硅单体、第一亲水性单体及交联剂,其中第一亲水性单体为N‑乙烯基吡咯烷酮,且硅高聚物及含羟基的硅单体与N‑乙烯基吡咯烷酮互溶。在硅水胶组合物中,硅高聚物的含量占组合物总量的重量百分比为5%~50%、含羟基的硅单体的含量占组合物总量的重量百分比为5%~50%、N‑乙烯基吡咯烷酮的含量占组合物总量的重量百分比为30%~60%及交联剂含量占组合物总量的重量百分比小于20%。此外,本发明还提供利用上述的硅水胶组合物制造的硅水胶镜片,其在使用中能持续维持有高透明度、高保湿度及高透氧度的性质。
Description
技术领域
本发明是有关于一种隐形眼镜镜片的材料,特别是有关一种用于隐形眼镜镜片的硅水胶组合物。
背景技术
由于硅水胶(silicone hydrogel)制成的隐形眼镜镜片(contact lens)具有高度透氧性,硅水胶镜片可以让充分的氧气能直接穿过镜片接触角膜,使角膜有足够的含氧量,即使长时间配戴,也较不易因角膜缺氧而造成眼睛不适的症状。因此,硅水胶已成为隐形眼镜镜片较佳的成分之一。
硅水胶镜片通常是由一种或二种硅胶单体、高聚物(macromer)或预聚物(prepolymer)所组成。由于这些成分本身为疏水性,使得镜片表面易缺水变干而造成眼睛不舒适。目前让硅水胶镜片表面保持湿润的方法如下,以电浆处理富含硅胶的疏水镜片表面;美国专利第6,367,929号、第6,822,016号、第7,052,131号、第7,649,058号、第7,666,921号、第7,691,916号及第8,168,720号提出在硅胶配方中加入亲水性聚合物,特别是聚-N-乙烯基吡咯烷酮(Polyvinyl pyrrolidone,PVP);另外,美国公开案第2006/0063852号中提出使用具有聚氧乙烯侧链的硅胶预聚物。然而,上述诸方法皆会造成制造过程上的困难,并增加硅水胶镜片的制造成本。
此外,硅胶容易吸收脂肪酸,使得脂肪酸沉积于镜片的表面造成视线模糊。因此,如何以亲水性单体与硅胶聚合制造出具有高透明度、高透氧度及高保湿度的隐形镜片,仍为业界需要面对的主要课题。
发明内容
基于现有技术所面临的问题,本发明的目的在于提供一种新奇的硅水胶组合物,其所制成的硅水胶镜片在使用中仍持续维持有高透明度、高保湿度及高透氧度的性质。
根据本发明的一方面,提供一种硅水胶组合物,其组成包含至少一种硅高聚物、一含羟基的硅单体、第一亲水性单体以及至少一种交联剂,其中第一亲水性单体为N-乙烯基吡咯烷酮,且硅高聚物、含羟基的硅单体或其组合与N-乙烯基吡咯烷酮互溶。
在本发明中,硅高聚物的含量占组合物总量的重量百分比为5%~50%,且其具有化学结构式(1)的化学结构:
其中X为亚氨基(-NH-)或氧,Y为亚氨基(-NH-)或氧,且X与Y至少有一个为亚氨基(-NH-),R1为氢或甲基,R2为C1-C10烷基,m为2~4的整数,n为2~4的整数,p为0~4的整数,q为2~4的整数,以及k是一使硅高聚物的平均分子量在600~3000的范围内的整数。硅与氮的原子数比为20:1~5:1。
含羟基的硅单体,其含量占组合物总量的重量百分比为5%~50%,且其具有化学结构式(2)的化学结构:
其中J为为氢或甲基,r为2~10的整数,K1、K2及K3为甲基或硅氧三甲基(-OSi(CH3)3),且K1、K2及K3至少有一为甲基或硅氧三甲基(-OSi(CH3)3)。
第一亲水性单体是为N-乙烯基吡咯烷酮(NVP),其含量占组合物总量的重量百分比为30%~60%,而交联剂的含量占组合物总量的重量百分比小于20%。
依据本发明一实施例,其中当化学结构式(1)的X为亚氨基(-NH-),Y为亚氨基(-NH-),m为2,p为0,q为3时,硅高聚物具有化学结构式(3)的化学结构:
其中k是使硅高聚物的平均分子量在600~3000的范围内的整数,R2为C1-C10烷基。
依据本发明另一实施例,其中当化学结构式(1)的X为亚氨基(-NH-),Y为氧,m为2,n为2,p为1,q为3时,硅高聚物具有化学结构式(4)的化学结构:
其中k是使硅高聚物的平均分子量在600~3000的范围内的整数,p为0~4的整数,R2为C1-C10烷基。
依据本发明另一实施例,硅高聚物的硅与氮的摩尔比为20:1~5:1。硅高聚物含有氨甲酸乙酯(urethane)、尿素(urea)或其组合。
依据本发明一实施例,其中当化学结构式(2)的J为甲基,r为3,K1为甲基、K2及K3为硅氧三甲基(-OSi(CH3)3),该含羟基的硅单体为(3-甲基丙烯酰氧基-2-羟基丙氧基)丙基双(三甲基硅氧基)甲基硅烷((3-methacryloxy-2-hydroxypropoxy)propylbis(trimethylsiloxy)methylsilane),其具有化学结构式(5)的化学结构:
依据本发明另一实施例,含羟基的硅单体分子量小于500,含羟基的硅单体中的硅与羟基的摩尔比为2:1~4:1。
依据本发明另一实施例,交联剂是选自由下列所组成的群组:乙二醇二甲基丙烯酸酯(ethylene glycol di(meth)acrylate,EGDA)、三甘醇二甲基丙烯酸酯(triethyleneglycol di(meth)acrylate)、伸丁二醇二甲基丙烯酸酯(tetramethylene glycol di(meth)acrylae)、三羟甲基丙烷三甲基丙烯酸酯(trimethylolpropane tri(meth)acrylate,TRIM)、新戊四醇四甲基丙烯酸酯(pentaerythritol tetra(meth)acrylate)、双酚A二甲基丙烯酸酯(bisphenol Adi(meth)acrylate)、亚甲基双甲基丙烯胺(methylenebis(meth)acrylamide)、二乙烯基醚(divinyl ether)、二乙烯基砜(divinylsulfone)、二乙烯基苯(divinyl benzene)、三乙烯基苯(trivinyl benzene)、三聚异氰酸三烯丙酯(triallyl isocyanurate)、邻苯二甲酸三烯丙酯(triallyl phthalate)、邻苯二甲酸二烯丙酯(diallyl phthalate)、甲基丙烯酸烯丙酯(allyl methacrylate)以及上述的组合。
依据本发明一实施例,还包含至少一种第二亲水性单体,其含量占该组合物总量的重量百分比为小于20%,且第二亲水性单体是选自由下列所组成的群组:甲基丙烯酸-2-羟基乙酯(2-hydroxyethyl methacrylate,HEMA)、甲基丙烯酸甘油酯(glycerolmethacrylate,GMA)、2-羟基丁基甲基丙烯酸酯(2-bydroxy-butyl methacrylate)、丙烯酸(acrylic acid)、甲基丙烯酸(methacrylic acid)、N,N-二甲基丙烯酰胺(N,N-dimethylacrylamide)、N,N-二甲基甲基丙烯酰胺(N,N-dimethyl methacrylamide)、N-乙烯基,N-甲基乙酰胺(N-vinyl,N-methyl acetamide)、2-甲基丙烯酰氧基乙基磷酸胆碱(2-methacryloyloxyethyl phosphorylcholine)以及上述的组合。
依据本发明另一实施例,还包含至少一种有色单体或有色化合物,有色单体例如为蓝色单体。
依据本发明另一实施例,还包含至少一种抗UV单体,抗UV单体例如为苯并三唑型单体。
依据本发明另一实施例,还包含至少一种有机溶剂,且有机溶剂是选自由下列所组成的群组:正丁醇(n-butanol)、叔丁醇(t-butanol)、正戊醇(n-pentyl alcohol)、叔戊醇(t-amyl alcohol)、正己醇(n-hexanol)、正辛醇(n-octanol)、正壬醇(n-nonanol)、正癸醇(n-decanol)、3-甲氧基-1-丁醇(3-methoxy-1-butanol)、甲基卡必醇(methylcabitol)、乙基卡必醇(ethyl carbitol)、丙基卡必醇(propyl carbitol)、丁基卡必醇(butyl carbitol)以及上述的组合。
依据本发明另一实施例,硅高聚物及含羟基的硅单体的含量占组合物总量的重量百分比为40%~70%。
依据本发明另一实施例,硅高聚物的含量占组合物总量的重量百分比为10%~30%、含羟基的硅单体的含量占组合物总量的重量百分比为10%~30%及N-乙烯基吡咯烷酮的含量占组合物总量的重量百分比为30%~50%。
本发明的另一方面在于提供一种硅水胶隐形眼镜镜片,其组成包含镜片主体,且此镜片主体是由上述硅水胶组合物制造而成。
本发明与现有技术相比,用本发明的硅水胶组合物所制成的硅水胶镜片在使用中可持续维持有高透明度、高保湿度及高透氧度的有益效果。
附图说明
图1A是本发明一实施方式的硅水胶镜片进行接触角量测的数字相机影像图。
图1B是放大第1A图的硅水胶镜片进行接触角量测的数字相机影像图。
具体实施方式
为了使本发明内容的叙述更加详尽与完备,下文针对了本发明的实施方式与具体实施例提出了说明性的描述;但这并非实施或运用本发明具体实施例的唯一形式。以下所公开的各实施例,在有益的情形下可相互组合或取代,也可在一实施例中附加其它的实施例,而无须进一步的记载或说明。
硅水胶组合物
硅水胶组合物包含至少一种硅高聚物、含羟基的硅单体、第一亲水性单体以及至少一种交联剂,且第一亲水性单体为N-乙烯基吡咯烷酮。本发明的硅高聚物、含羟基的硅单体或其组合皆可与N-乙烯基吡咯烷酮以任何比例互溶,且由于N-乙烯基吡咯烷酮具有极度亲水性,因此本发明的硅水胶组合物具有极性较高的性质。相比已知的极性较低的硅高聚物及预聚物,本发明所包含的硅高聚物及含羟基的硅单体相对亲水,故再配合与具有极度亲水性的N-乙烯基吡咯烷酮共聚,其所制成的硅水胶镜片能高度保湿,且镜片表面不易失去水分。
本发明所称的硅单体是指可聚合的单一分子量的硅化合物,通常其分子量小于600。硅高聚物是指可聚合的硅高分子混合物其平均分子量大于600,其中每个分子具有一个可聚合的双键以及至少两个连续性的双甲基硅氧烷(diemthylsiloxane)单位。硅预聚物定义与硅高聚物的差异在于它有至少两个可聚合的双键。
硅高聚物的含量占组合物总量的重量百分比为5%~50%,且其具有化学结构式(1)的化学结构:
其中X为亚氨基(-NH-)或氧,Y为亚氨基(-NH-)或氧,且X与Y至少有一个为亚氨基(-NH-),R1为氢或甲基,R2为C1-C10烷基,m为2~4的整数,n为2~4的整数,p为0~4的整数,q为2~4的整数,以及k是使硅高聚物的平均分子量在600~3000的范围内的整数,且硅与氮的原子数比为20:1~5:1。
在一实施例中,其中当化学结构式(1)的X为亚氨基(-NH-),Y为亚氨基(-NH-),m为2,p为0,q为3时,硅高聚物具有化学结构式(3)的化学结构:
其中k是使硅高聚物的平均分子量在600~3000的范围内的整数,R2为C1-C10烷基。
在另一实施例中,其中当化学结构式(1)的X为亚氨基(-NH-),Y为氧,m为2,n为2,p为1,q为3时,硅高聚物具有化学结构式(4)的化学结构:
其中k是使硅高聚物的平均分子量在600-3000的范围内的整数,p为0~4的整数,R2为C1-C10烷基。
在一实施例中,硅高聚物的分子量范围为600-3000,且硅高聚物的硅与氮的摩尔比为20:1~5:1。在另一实施例中,硅高聚物的硅与氮的摩尔比为10:1~5:1。在又一实施例中,硅高聚物含有氨基甲酸乙酯(urethane)、尿素(urea)或其组合。
含羟基的硅单体,其含量占组合物总量的重量百分比为5%~50%,且其具有化学结构式(2)的化学结构:
其中J为为氢或甲基,r为2~10的整数,K1、K2及K3为甲基或硅氧三甲基(-OSi(CH3)3),且K1、K2及K3至少有一个为甲基或硅氧三甲基(-OSi(CH3)3)。
在一实施例中,其中当化学结构式(2)的J为甲基,r为3,K1为甲基、K2及K3为硅氧三甲基(-OSi(CH3)3),含羟基的硅单体为(3-甲基丙烯酰氧基-2-羟基丙氧基)丙基双(三甲基硅氧基)甲基硅烷((3-methacryloxy-2-hydroxypropoxy)propylbis(trimethylsiloxy)methylsilane),其具有化学结构式(5)的化学结构:
在另一实施例中,含羟基的硅单体分子量小于500,且含羟基的硅单体中的硅与羟基的摩尔比为2:1~4:1。
交联剂占组合物总量的重量百分比小于20%。在一实施例中,交联剂是选自由下列所组成的群组:乙二醇二甲基丙烯酸酯(ethylene glycol di(meth)acrylate,EGDA)、三甘醇二甲基丙烯酸酯(triethylene glycol di(meth)acrylate)、伸丁二醇二甲基丙烯酸酯(tetramethylene glycol di(meth)acrylae)、三羟甲基丙烷三甲基丙烯酸酯(trimethylolpropane tri(meth)acrylate,TRIM)、新戊四醇四甲基丙烯酸酯(pentaerythritol tetra(meth)acrylate)、双酚A二甲基丙烯酸酯(bisphenol A di(meth)acrylate)、亚甲基双甲基丙烯胺(methylenebis(meth)acrylamide)、二乙烯基醚(divinyl ether)、二乙烯基砜(divinyl sulfone)、二乙烯基苯(divinyl benzene)、三乙烯基苯(trivinyl benzene)、三聚异氰酸三烯丙酯(triallyl isocyanurate)、邻苯二甲酸三烯丙酯(triallyl phthalate)、邻苯二甲酸二烯丙酯(diallyl phthalate)与甲基丙烯酸烯丙酯(allyl methacrylate)以及上述的组合。
硅水胶组合物还包含至少一种第二亲水性单体,其含量占组合物总量的重量百分比为小于20%。在一实施例中,第二亲水性单体是选自由下列所组成的群组:甲基丙烯酸-2-羟基乙酯(2-hydroxyethyl methacrylate,HEMA)、甲基丙烯酸甘油酯(glycerolmethacrylate,GMA)、2-羟基丁基甲基丙烯酸酯(2-bydroxy-butyl methacrylate)、丙烯酸(acrylic acid)、甲基丙烯酸(methacrylic acid)、N,N-二甲基丙烯酰胺(N,N-dimethylacrylamide)、N,N-二甲基甲基丙烯酰胺(N,N-dimethyl methacrylamide)、N-乙烯基,N-甲基乙酰胺(N-vinyl,N-methyl acetamide)、2-甲基丙烯酰氧基乙基磷酸胆碱(2-methacryloyloxyethyl phosphorylcholine)以及上述的组合。
硅水胶组合物还包含至少一种有色单体或有色化合物;在一实施例中,有色单体为蓝色单体。
硅水胶组合物还包含至少一种抗UV单体;在一实施例中,抗UV单体为苯并三唑型单体。
因本发明使用的含羟基的硅单体及硅高聚物可与亲水性单体N-乙烯基吡咯烷酮完全互溶,因此不需要添加溶剂到此硅水胶组合物,以便聚合形成透明的镜片。然而,此特点也让此类硅水胶组成在做镜片的制造过程上具较多的弹性,例如在干片脱模的过程。上述的特性为现所知的绝大部分硅水胶所没有的。
如有需要,本发明的硅水胶组合物也可进一步包含至少一种有机溶剂。在一实施例中,有机溶剂是选自由下列所组成的群组:正丁醇(n-butanol)、叔丁醇(t-butanol)、正戊醇(n-pentyl alcohol)、叔戊醇(t-amyl alcohol)、正己醇(n-hexanol)、正辛醇(n-octanol)、正壬醇(n-nonanol)、正癸醇(n-decanol)、3-甲氧基-1-丁醇(3-methoxy-1-butanol)、甲基卡必醇(methyl cabitol)、乙基卡必醇(ethyl carbitol)、丙基卡必醇(propyl carbitol)、丁基卡必醇(butyl carbitol)以及上述的组合。
在另一实施例中,硅高聚物的含量占组合物总量的重量百分比为10%~30%、含羟基的硅单体的含量占组合物总量的重量百分比为10%~30%、及N-乙烯基吡咯烷酮的含量占组合物总量的重量百分比为30%~50%。
上述硅水胶组合物可应用于生物医学领域中,特别可用以作为硅水胶镜片中的主要成分,但不限于此。
硅水胶镜片
硅水胶镜片的组成包含镜片主体,且此镜片主体是由上述硅水胶组合物制造而成。
制造上述硅水胶镜片的方法如下,首先,将硅水胶组合物注入制造镜片的模具内,并对模具内的硅水胶组合物聚合进行固化处理,以形成该聚合镜片主体,接着对镜片主体进行镜片脱模,然后将镜片主体浸泡水中,以水化聚合镜片主体,并将镜片主体密封于包含包装溶液的包装中,再对经密封包装实施灭菌。
制造隐形眼镜镜片的模具是由热塑性聚合物所形成,例如聚丙烯;其构造是由凹模构件及凸模构件组成,凹模构件用以填充足以形成镜片主体的量的硅水胶组合物,凸模构件是耦合至凹模构件,以形成具有镜片形空腔的模具,而形成镜片主体的材料是位于镜片型空腔之间。
镜片模具内的硅水胶组合物是使用任一种适当固化方法来聚合,例如:紫线光(UV)固化或热固化(thermal curing)。UV固化的方法如下,首先将定量约为65微升的硅水胶组合物(包含硅高聚物、含羟基的硅单体、N-乙烯基吡咯烷酮、蓝色单体、光起始剂及有机溶剂)注入到凹模构件中,再将凸模构件置于凹模构件的上方,然后将组合好的镜片模具置于UV光下固化约10~15分钟,以形成聚合镜片主体。上述的光起始剂例如为安息香甲基醚、1-羟基环己基苯基酮、Darocur-1173或Irgacur-819。
热固化的方法如下,将装有硅水胶组合物的的模具置于烘箱中,并将其密封,接着抽出烘箱中的空气约30分钟,然后用氮气填充,直到微正压,然后将进行第一阶段增温至55℃,停留约60分钟,进行第二阶段增温至70℃,然后停留约30分钟,进行第三阶段增温至90℃,停留约30分钟,再进行第四阶段增温至110℃,并维持约30分钟。上述的硅水胶组合物包含热起始剂,热起始剂为2,2-偶氮双(2,4-二甲基戊腈)、2,2-偶氮双(2-甲基丙腈)及1,1-偶氮双(氰基环己烷)。
固化处理后,移除凸模构件,接着进行镜片脱模,镜片脱模的方式例如为湿式脱膜或干式脱模。在一实施例中,以异丙醇萃取聚合镜片主体,时间约为四小时,然后放入异丙醇/水(50/50v/v)中浸泡约一小时,再浸泡于去离子水中,其后即做镜片的外观检测。
通过检测的聚合镜片主体置于包含包装溶液的包装中,接着,将包装密封后,高压灭菌30分钟。上述的包装溶液为pH值为7.0~7.4之间的缓冲液,例如为硼酸盐缓冲盐水或磷酸盐缓冲盐水。灭菌后的硅水胶镜片是为眼科所用的隐形眼镜。此时即可进行各项主要参数检测,包含平衡水含量、拉伸模数、摩擦系数、透氧性及接触角。
实施例
以下的实施例是用以详述本发明的特定态样,并使本发明所属技术领域中本领域技术人员得以实施本发明。以下的实施例不应用以限制本发明。
制造化学结构式(3)的硅高聚物
在配备有回流冷凝器和氮气层的1公升三颈圆底烧瓶中添加300克的单胺基丙基封端的聚二甲基硅氧烷(monoaminopropyl-terminated polydimethylsiloxane)(数量平均分子量(Mn)为900)、250毫升的二氯甲烷(dichloromethane)及1.2毫克的二月桂酸二丁基锡(dibutyltin dilaurate);然后,将111.71克丙烯基氧乙基异氰酸酯(methacryloyloxyethyl isocyanate)(相对于聚二甲基硅氧烷至少1.5倍)缓慢地加入溶液中,此步骤反应时间是需超过30分钟,再于室温下将混合物搅拌4小时;接着,将28.8克甲醇缓慢地加入混合物中,此步骤反应时间是需超过20分钟,再另外搅拌2小时;接着,在减压下移除二氯甲烷,然后进一步将粗产物进行纯化并干燥,可310克的硅高聚物,其产量为85%,其数量平均分子量(Mn)为1223,分散度(polydispersity)为1.23(使用尺寸筛除层析法测其分散度,以聚苯乙烯为标准品)。最后以核磁共振频谱(NMR)确认其结构。
制造化学结构式(4)的硅高聚物
化学结构式(4)的硅高聚物的制造方法如同上述化学结构式(3)的硅高聚物的制造方法,唯其不同处在于以甲醇封端的聚二甲基硅氧烷(carbinol-terminatedpolydimethylsiloxane)(Mn 950)取代胺丙基封端的聚二甲基硅氧烷(monoaminopropyl-terminated polydimethylsiloxane)。可得硅高聚物的310克,其产量为89%,数量平均分子量(Mn)为1277,分散度(polydispersity)为1.21,并以核磁共振频谱(NMR)确认其结构。
实施例A1~A4:溶解度分析
将硅高聚物、含羟基的硅单体或其组合与N-乙烯基吡咯烷酮(NVP)混合于容器中,摇晃均匀后观察其透明度,N-乙烯基吡咯烷酮与硅高聚合物的相互溶解度越高,混合溶液越透明。其中,比较例A为混合NVP及不含氮基的硅高聚物,此不含氮基的硅高聚物其平均分子量与化学结构式(3)及(4)的硅高聚物相近,约为1100。实施例A1为混合NVP及化学结构式(3)的硅高聚物,实施例A2为混合NVP及化学结构式(4)的硅高聚物,实施例A3为混合NVP、化学结构式(3)的硅高聚物及化学结构式(5)的含羟基的硅单体,其中化学结构式(5)的含羟基的硅单体与化学结构式(3)的硅高聚物的比例为3:1,实施例A4为混合NVP、化学结构式(3)的硅高聚物及化学结构式(5)的含羟基的硅单体,其中化学结构式(5)的含羟基的硅单体与化学结构式(3)的硅高聚物的比例为1:3。溶解度分析结果如下列表一:
表一
当N-乙烯基吡咯烷酮与不含氮基的硅高聚物混合的比值高于0.7时,其混合溶液呈混浊状态,这是因为N-乙烯基吡咯烷酮极性极高,而不含氮基的硅高聚物完全没极性,故当N-乙烯基吡咯烷酮与不含氮基的硅高聚物混合的比例高于0.7时无法互溶。而本发明的硅高聚物因含有高极性的氨基甲酸乙酯(urethane)及尿素(urea),当硅高聚物的官能基(以氮的数目计)与非极性的硅烷量(以硅的数目计)比例高于一定值,N-乙烯基吡咯烷酮与此含氮基的硅高聚物可以任何比例皆可互溶,使混合溶液完全澄清透明。
此外,当N-乙烯基吡咯烷酮与化学结构式(5)的含羟基的硅单体的比值为0.12-10时,其混合溶液均呈澄清状态。由于羟基极性高且具有高度亲水性,因此,当此类单体的羟基与硅的比例高于一定值时,N-乙烯基吡咯烷酮能与含羟基的硅单体以任何比例互溶。
相关参数分析
实施例B1~B6及实施例C1~C6:平衡水含量(EWC)、氧透量及拉伸模数分析
依照上述任一实施例,并参照表二所列出不同配方的硅水胶组合物制造硅水胶镜片,然后分析其相关参数:平衡水含量(EWC)、氧透量及拉伸模数,如在以下段落中详细说明。
平衡水含量的量测方法为去除镜片表面的水并称量,以获得水合重量,接着在烘箱中对镜片进行干燥并称量,水合重量减去干燥镜片的重量可得重量差。镜片的平衡水含量(wt%)=(重量差/水合重量)x100。
透氧量的量测可使用任何习知方法,例如:ISO 9913-1中的极谱分析法,并使用Model 201T透氧率测试仪。其中所有待测样品进行测量前需先浸泡于纯水中,待其达到平衡至少24小时,再浸泡于PBS中,待其达到平衡至少12小时,然后使用Model 201T透氧率测试仪(购自Rheder Development Company)于35℃进行测量,所得透氧量的单位为Barrers。
拉伸模数是由拉伸试验机测量,例如型号为Zwick Z0.5的拉伸试验机。其中待测样品需切成宽度2mm,并以测微计测量待测样品的厚度。测试前需先固定待测样品伸缩的移动速度、待测样品的长度及夹钳口的间距。测试过程中,所有测量对象浸泡于测定在缓冲盐水中。拉伸模数的单位为MPa。
下列表二为实施例B1~B6及C1~C6的配方,其主要成份至少含一种硅高聚物、(3-甲基丙烯酰氧基-2-羟基丙氧基)丙基双(三甲基硅氧基)甲基硅烷、N-乙烯基吡咯烷酮(NVP)以及乙二醇二甲基丙烯酸酯(EGDMA);此外,表二中也列出以上述实施例制造的镜片的相关参数测量结果,包含平衡水含量、氧透量及拉伸模数。
表二
经由表二分析结果得知,本发明的任一实施例所制造的硅水胶镜片,无论是平衡水含量(EWC)、氧透量或拉伸模数皆于正常数值范围。亲水性单体(HEMA)的加入并未影响其产物的性质,表示本发明的硅水胶镜片其材料本身极具亲水性,因此不需额外加入亲水性单体来提升其平衡含水量。
实施例C4及比较例B1~B4:接触角及摩擦系数分析
比较例B1~B4为主要市场销售的隐形眼镜,其中比较例B1的主要成分为Senofilcon A,其平衡含水量为38wt%;比较例B2的主要成分为Comfilcon A,其平衡含水量为48wt%;比较例B3的主要成分为Lotrafilcon B,其平衡含水量为33wt%;比较例B4的主要成分为Balafilcon A,其平衡含水量为36wt%。然后进行摩擦系数及接触角的分析,如在以下段落中详细说明。
接触角可使用熟悉本领域技术人员已知的常规方法来测定,例如捕泡法。捕泡法为将聚硅氧水凝胶镜片夹于两个硬质塑料间,使镜片中心部分较为平坦,然后将镜片浸入填充硼酸盐缓冲盐水溶液中的ㄧ凹槽。接着,将气泡注射于镜片表面,并停留在表面上,然后拍照并计算镜片的左与右的接触角,再取其平均数。举例来说,图1A是本发明的硅水胶镜片进行接触角量测的数字相机影像图,而图1B是放大图1A的硅水胶镜片进行接触角量测的数字相机影像图。如图1B所示,左接触角量测θ1为11°,右接触角量测θ2为12°。
测量摩擦系数的方法:测量前,镜片浸泡于硼酸盐缓冲盐水溶液中,然后使用摩擦测试计测量摩擦系数,并使用人工泪液100μL作为润滑液。上述摩擦测试计的测量条件如下,镜片载重为3毫牛/米(mN/m),滑动速度为30毫米/分钟,基板材料为聚对苯二甲酸乙烯酯。每个待测样品重复测量数次并取其平均值。
下列表三为实施例C3及比较例B1~B4的平均接触角及摩擦系数的测量结果。
表三
经由表三分析结果得知,本发明的硅水胶镜片测得平均接触角于11度~15度的范围内;而其它市场销售的隐形眼镜作为比较例,所测得结果均大于25度。通过量测镜片表面接触角,以判断镜片的可湿性,故可知本发明的硅水胶镜片具有高度的可湿性。
另外,隐形眼镜镜片表面的润滑性直接影响其配戴于眼睛上的舒适性,可通过量测镜片表面的摩擦系数,以判断镜片的配戴舒适度。当摩擦系数越低,表示镜片表面的润滑性越高,眼睛配戴时越为舒适。经由表三分析结果得知,其它市场销售的隐形眼镜作为实施例,所测得的摩擦系数于0.003~0.4的范围,而本发明的硅水胶镜片测得的摩擦系数为约0.006,故可知本发明的硅水胶镜片配戴于眼睛上具有良好的舒适度。
应说明的是:以上实施例仅用以说明本发明而非限制,本发明也并不仅限于上述举例,一切不脱离本发明的精神和范围的技术方案及其改进,其均应涵盖在本发明的权利要求范围中。
Claims (19)
1.一种硅水胶组合物,其特征在于,包含:
至少一种硅高聚物,其含量占所述组合物总量的重量百分比为5%~50%,所述硅高聚物具有化学结构式(1)的化学结构:
其中,X为亚氨基(-NH-),Y为亚氨基(-NH-),R1为氢或甲基,R2为C1-C10烷基,m为2~4的整数,n为2~4的整数,p为0~4的整数,q为2~4的整数,以及k是使所述硅高聚物的平均分子量在600-3000的范围内的整数;
含羟基的硅单体,其含量占所述组合物总量的重量百分比为5%~50%,且所述含羟基的硅单体的硅与羟基比为4:1~2:1;
N-乙烯基吡咯烷酮,其含量占所述组合物总量的重量百分比为30%~60%,其中,所述硅高聚物、所述含羟基的硅单体或其组合与N-乙烯基吡咯烷酮互溶;以及
至少一种交联剂,其含量占所述组合物总量的重量百分比小于20%,其中所述硅水胶组合物不包含2-甲基丙烯酰氧基乙基磷酸胆碱。
2.一种硅水胶组合物,其特征在于,包含:
至少一种硅高聚物,其含量占所述组合物总量的重量百分比为5%~50%,所述硅高聚物具有化学结构式(1)的化学结构:
其中,X为亚氨基(-NH-),Y为亚氨基(-NH-),R1为氢或甲基,R2为C1-C10烷基,m为2~4的整数,n为2~4的整数,p为0~4的整数,q为2~4的整数,以及k是使所述硅高聚物的平均分子量在600-3000的范围内的整数;
含羟基的硅单体,其含量占所述组合物总量的重量百分比为5%~50%,所述含羟基的硅单体具有化学结构式(2)的化学结构:
其中,J为氢或甲基,r为2~10的整数,K1、K2及K3为甲基或硅氧三甲基(-OSi(CH3)3),且K1、K2及K3至少有一个为甲基及硅氧三甲基(-OSi(CH3)3);
第一亲水性单体,其含量占所述组合物总量的重量百分比为30%~60%,其中所述第一亲水性单体为N-乙烯基吡咯烷酮,且所述硅高聚物、所述含羟基的硅单体或其组合与N-乙烯基吡咯烷酮互溶;以及
至少一种交联剂,其含量占所述组合物总量的重量百分比小于20%,其中所述硅水胶组合物不包含2-甲基丙烯酰氧基乙基磷酸胆碱。
3.如权利要求2所述的硅水胶组合物,其特征在于,m为2,p为0,q为3,所述硅高聚物具有化学结构式(3)的化学结构:
4.如权利要求2所述的硅水胶组合物,其特征在于,所述硅高聚物的硅与氮的摩尔比为20:1~5:1。
5.如权利要求2所述的硅水胶组合物,其特征在于,所述硅高聚物的硅与氮的摩尔比为10:1~5:1。
6.如权利要求2所述的硅水胶组合物,其特征在于,所述硅高聚物含有氨基甲酸乙酯、尿素或其组合。
7.如权利要求2所述的硅水胶组合物,其特征在于,所述含羟基的硅单体分子量小于500。
8.如权利要求2所述的硅水胶组合物,其特征在于,所述含羟基的硅单体中的硅与羟基的摩尔比为2:1~4:1。
9.如权利要求2所述的硅水胶组合物,其特征在于,当化学结构式(2)的J为甲基,r为3,K1为甲基、K2及K3为硅氧三甲基(-OSi(CH3)3),所述含羟基的硅单体为(3-甲基丙烯酰氧基-2-羟基丙氧基)丙基双(三甲基硅氧基)甲基硅烷,其具有化学结构式(5)的化学结构:
10.如权利要求2所述的硅水胶组合物,其特征在于,所述交联剂是选自由下列所组成的群组:乙二醇二甲基丙烯酸酯、三甘醇二甲基丙烯酸酯、伸丁二醇二甲基丙烯酸酯、三羟甲基丙烷三甲基丙烯酸酯、新戊四醇四甲基丙烯酸酯、双酚A二甲基丙烯酸酯、亚甲基双甲基丙烯胺、二乙烯基醚、二乙烯基砜、二乙烯基苯、三乙烯基苯、三聚异氰酸三烯丙酯、邻苯二甲酸三烯丙酯、邻苯二甲酸二烯丙酯与甲基丙烯酸烯丙酯以及上述的组合。
11.如权利要求2所述的硅水胶组合物,其特征在于,还包含至少一种第二亲水性单体,其含量占所述组合物总量的重量百分比小于20%,且所述第二亲水性单体是选自由下列所组成的群组:甲基丙烯酸-2-羟基乙酯、甲基丙烯酸甘油酯、2-羟基丁基甲基丙烯酸酯、丙烯酸、甲基丙烯酸、N,N-二甲基丙烯酰胺、N,N-二甲基甲基丙烯酰胺、N-乙烯基,N-甲基乙酰胺以及上述的组合。
12.如权利要求2所述的硅水胶组合物,其特征在于,还包含至少一种有色单体或有色化合物。
13.如权利要求12所述的硅水胶组合物,其特征在于,所述有色单体为蓝色单体。
14.如权利要求2所述的硅水胶组合物,其特征在于,还包含至少一种抗UV单体。
15.如权利要求14所述的硅水胶组合物,其特征在于,所述抗UV单体为苯并三唑型单体。
16.如权利要求2所述的硅水胶组合物,其特征在于,还包含至少一种有机溶剂,且所述有机溶剂是选自由下列所组成的群组:正丁醇、叔丁醇、正戊醇、叔戊醇、正己醇、正辛醇、正壬醇、正癸醇、3-甲氧基-1-丁醇、甲基卡必醇、乙基卡必醇、丙基卡必醇、丁基卡必醇以及上述的组合。
17.如权利要求2所述的硅水胶组合物,其特征在于,所述硅高聚物及所述含羟基的硅单体含量占所述组合物总量的重量百分比为40%~70%。
18.如权利要求2所述的硅水胶组合物,其特征在于,所述硅高聚物含量占所述组合物总量的重量百分比为10%~30%、所述含羟基的硅单体的含量占所述组合物总量的重量百分比为10%~30%及N-乙烯基吡咯烷酮的含量占所述组合物总量重量百分比为30%~50%。
19.一种硅水胶镜片,其特征在于,包含:
镜片主体,其是由权利要求1至18中的任一项的硅水胶组合物制造而成。
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CN102576158A (zh) * | 2009-10-01 | 2012-07-11 | 库柏维景国际控股公司 | 硅酮水凝胶隐形眼镜和制造硅酮水凝胶隐形眼镜的方法 |
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US9046641B2 (en) | 2015-06-02 |
TWI496838B (zh) | 2015-08-21 |
TW201420678A (zh) | 2014-06-01 |
JP6165450B2 (ja) | 2017-07-19 |
JP2014109028A (ja) | 2014-06-12 |
EP2738221A1 (en) | 2014-06-04 |
US20140155515A1 (en) | 2014-06-05 |
CN103848946A (zh) | 2014-06-11 |
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