CN109563229B - 用于聚硫代氨基甲酸酯类光学材料的聚合性组合物 - Google Patents
用于聚硫代氨基甲酸酯类光学材料的聚合性组合物 Download PDFInfo
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- CN109563229B CN109563229B CN201780047593.9A CN201780047593A CN109563229B CN 109563229 B CN109563229 B CN 109563229B CN 201780047593 A CN201780047593 A CN 201780047593A CN 109563229 B CN109563229 B CN 109563229B
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- polythiourethane
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- 239000000203 mixture Substances 0.000 title claims abstract description 54
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- 239000000463 material Substances 0.000 title claims abstract description 47
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- 229920006295 polythiol Polymers 0.000 claims description 50
- -1 isocyanate compound Chemical class 0.000 claims description 44
- 150000001768 cations Chemical class 0.000 claims description 19
- 239000012535 impurity Substances 0.000 claims description 19
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Abstract
本发明一实施方式涉及用于聚硫代氨基甲酸酯类光学材料的聚合性组合物,其中包含特定添加剂的所述聚合性组合物可以适当地调节异氰酸酯的反应性,使得在预定的时间段内保持较低的粘度,因此能够制备高质量聚硫代氨基甲酸酯类光学材料而无需复杂的纯化过程。此外,根据一实施方式的聚硫代氨基甲酸酯类光学材料不仅具有均匀的折射率,而且具有低的黄度指数,因此可以用作各种塑料光学镜片,例如眼镜镜片或相机镜头等。
Description
技术领域
本发明实施方式涉及用于聚硫代氨基甲酸酯类光学材料的聚合性组合物,以及由其制备的聚硫代氨基甲酸酯类光学材料。
背景技术
与由玻璃等无机材料构成的光学材料相比,塑料类光学材料重量轻,具有良好的染色性能,并且不易破碎。因此,各种树脂的塑料材料被广泛用作眼镜镜片、相机镜头等的光学材料。近年来,随着对更高性能和便利性的需求增加,人们对具有高透明度、高折射率、高阿贝数、低比重、高耐热性、高抗冲击性等性能的光学材料的研究仍在继续。
广泛使用的光学材料的一个例子是通过使多硫醇类化合物和异氰酸酯类化合物进行聚合所获得的聚硫代氨基甲酸酯化合物。然而,当通过使多硫醇类化合物和异氰酸酯类化合物反应来制备聚硫代氨基甲酸酯类光学材料时,金属阳离子材料(例如,Ca、Mg、K、Na等阳离子)或含氮化合物(例如,胺等)等来自多硫醇化合物的杂质通常会增加异氰酸酯化合物的反应性,从而引起快速固化,导致制备目标聚硫代氨基甲酸酯光学材料的困难。此外,结果,制得的光学材料可能显示出部分不均匀的折射率。
因此,为了减少多硫醇中的杂质含量或调节多硫醇与异氰酸酯之间的反应性,人们做了各种各样的努力。
例如,韩国专利No.10-1338568公开了一种通过使用钙含量至多为1.0wt%的硫脲来制备多硫醇化合物的方法。然而,处理硫脲是困难的,并且存在多硫醇化合物的质量根据纯化方法而大幅变化的问题。
此外,韩国专利No.10-1205467公开了一种通过调节多硫醇的pH至3.1-7之间来调节多硫醇与异氰酸酯之间反应性的方法。然而,由于多硫醇需要用酸性和碱性水溶液洗涤数次以调节多硫醇的pH,因此存在产生废水、工艺产量降低和多硫醇的光学性能恶化等问题。
此外,韩国专利No.10-1533207公开了一种通过使用多硫醇制造塑料镜片的方法,其中含氮化合物的含量至多为3wt%。然而,含氮化合物的含量即使在制备聚硫醇的方法相同的情况下也会发生变化,从而导致质量控制的困难。
发明内容
技术问题
因此,本发明一实施方式的一个目的是提供一种能够制备高质量聚硫代氨基甲酸酯类光学材料的聚合性组合物而无需复杂的纯化过程。
问题的解决方案
本发明一实施方式提供了一种聚合性组合物,包括:(i)多硫醇化合物;(ii)异氰酸酯化合物;以及(iii)酸组分,所述酸组分包括一价至四价的羧酸、磷酸或其混合。
另一实施方式提供了由所述聚合性组合物得到的一种聚硫代氨基甲酸酯类化合物。
又一实施方式提供了由所述聚硫代氨基甲酸酯类化合物模塑而成的光学材料。
本发明的有益效果
根据一个实施方式,包含特定添加剂的聚合性组合物可以适当地调节异氰酸酯的反应性,使得在预定的时间段内保持较低的粘度,因此,能够制备高质量的聚硫代氨基甲酸酯类光学材料,且没有复杂的纯化过程。而且,聚硫代氨基甲酸酯类光学材料不仅具有均匀的折射率,而且具有低的黄度指数,因此可以用作各种塑料光学镜片,例如眼镜镜片或相机镜头等。
实施本发明的最佳方式
一实施方式提供了一种聚合性组合物,包括:(i)多硫醇化合物;(ii)异氰酸酯化合物;以及(iii)酸组分,所述酸组分包括一价至四价的羧酸、磷酸或其混合。
所述酸组分与多硫醇化合物中的残余杂质—金属阳离子材料和含氮化合物形成盐,从而适当地调节异氰酸酯的反应性,以防止快速固化并诱导聚硫代氨基甲酸酯类化合物的稳定聚合。
所述羧酸可以是选自由单价饱和脂肪酸(例如甲酸、乙酸、丙酸、丁酸、戊酸、己酸、庚酸、辛酸、壬酸、癸酸、十一烷酸、十二烷酸、十三烷酸、十四烷酸、十五烷酸、十六烷酸、十七烷酸、十八烷酸(硬脂酸)、十九烷酸、二十烷酸等)、单价不饱和脂肪酸(例如十一烯酸、棕榈油酸、油酸、亚油酸、花生四烯酸、芥酸等)、二羧酸(例如乙二酸(草酸)、丙二酸、丁二酸、戊二酸、己二酸、庚二酸、辛二酸、壬二酸、癸二酸、十一烷二酸、十二烷二酸、十六烷二酸、马来酸、富马酸、戊烯二酸、愈伤酸、粘康酸、戊炔二酸、柠康酸、中康酸、羟基丁二酸、2-氨基丁二酸、2-氨基戊二酸、2-羟基丙二酸、2,3-二羟基丁二酸、(2R、6S)-2,6-二氨基庚二酸、(2S,3S,4S,5R)-2,3,4,5-四羟基己二酸、氧代丙二酸、氧代丁二酸、3-氧代戊二酸、2,3,4-三羟基戊二酸等)、芳香族二羧酸(例如苯-1,2-二羧酸、苯-1,3-二羧酸、苯-1,4-二羧酸、2-(2-羧基苯基)苯甲酸、2,6-萘二甲酸等)、三羧酸(例如2-羟基丙烷-1,2,3-三羧酸、1-羟基丙烷-1,2,3-三羧酸、丙-1-烯-1,2,3-三羧酸、丙烷-1,2,3-三羧酸、苯-1,3,5-三羧酸等)、巯基乙酸、2-羟基丁酸、硫羟乳酸、3-羟基丁酸、3-巯基丙酸和4-羟基丁酸组成的群中的一种或多种。具体地,所述羧酸可以是选自由油酸、草酸、棕榈油酸、亚油酸、丙二酸和丁二酸组成的群中的一种或多种。
所述酸组分可以是选自由油酸、草酸、棕榈油酸、亚油酸、丙二酸、丁二酸和磷酸组成的群中的一种或多种。
相对于100重量份的所述多硫醇化合物和异氰酸酯化合物的总和,所述聚合性组合物可包含0.1-1重量份的酸组分。具体地,相对于100重量份的所述多硫醇化合物和异氰酸酯化合物的总和,所述聚合性组合物可包含0.2-0.85重量份或0.3-0.7重量份的酸组分。
所述多硫醇化合物可以是合成聚硫代氨基甲酸酯中使用的一种典型的多硫醇化合物。具体地,所述多硫醇化合物可以包括选自由双(2-(2-巯基乙硫基)-3-巯基丙基)硫醚、4-巯基甲基-1,8-二巯基-3,6-二硫杂辛烷、2,3-双(2-巯基乙硫基)丙烷-1-硫醇、2,2-双(巯基甲基)-1,3-丙二硫醇、双(2-巯基乙基)硫醚、四(巯基甲基)甲烷、2-(2-巯基乙硫基)丙烷-1,3-二硫醇、2-(2,3-双(2-巯基乙硫基)丙硫基)乙硫醇、双(2,3-二巯基丙烷基)硫醚、双(2,3-二巯基丙烷基)二硫醚、1,2-双(2-巯基乙硫基)-3-巯基丙烷、1,2-双(2-(2-巯基乙硫基)-3-巯基丙硫基)乙烷、2-(2-巯基乙硫基)-3-2-巯基-3-[3-巯基-2-(2-巯基乙硫基)丙硫基]丙硫基-丙烷-1-硫醇、2,2-双-(3-巯基-丙酰氧基甲基)-丁酯、2-(2-巯基乙硫基)-3-(2-(2-[3-巯基-2-(2-巯基乙硫基)丙硫基]乙硫基)乙硫基)丙烷-1-硫醇、(4R,11S)-4,11-双(巯基甲基)-3,6,9,12-硫杂十四烷-1,14-二硫醇、(S)-3-((R-2,3-二巯基丙基)硫代)丙烷-1,2-二硫醇、(4R,14R)-4,14-二(巯基甲基)-3,6,9,12,15-五硫杂庚烷-1,17-二硫醇、(S)-3-((R-3-巯基-2-((2-巯基乙基)硫代)丙基)硫代)丙基)硫代)-2-((2-巯基乙基)硫代)丙烷-1-硫醇、3,3'-二硫代双(丙烷-1,2-二硫醇)、(7R,11S)-7,11-双(巯基甲基)-3,6,9,12,15-五硫杂十七烷-1,17-二硫醇、(7R,12S)-7,12-双(巯基甲基)-3,6,9,10,13,16-六硫杂十八烷-1,18-二硫醇、5,7-二巯基甲基-1,11-二巯基-3,6,9-三硫杂十一烷、4,7-二巯基甲基-1,11-二巯基-3,6,9-三硫杂十一烷、4,8-二巯基甲基-1,11-二巯基-3,6,9-三硫杂十一烷、季戊四醇四(3-巯基丙酸酯)、三羟甲基丙烷三(3-巯基丙酸酯)、季戊四醇四(2-巯基乙酸酯)、双季戊四醇六(3-巯基丙酸酯)、1,1,3,3-四(巯基甲硫基)丙烷、1,1,2,2-四(巯基甲硫基)乙烷、4,6-双(巯基甲硫基)-1,3-二噻烷和2-(2,2-双(巯基二甲硫基)乙基)-1,3-二硫杂乙烷组成的群中的一种或多种。
所述多硫醇化合物可以包括金属阳离子杂质、含氮杂质或其混合。
所述多硫醇化合物可以包括100-6000ppm的金属阳离子杂质。具体地,所述多硫醇化合物可以包括500-5000ppm的金属阳离子杂质。此外,所述金属阳离子杂质可以是选自由Ca阳离子、Mg阳离子、K阳离子和Na阳离子组成的群中的一种或多种。
基于所述多硫醇化合物的总重量,所述多硫醇化合物可以包括3-10wt%的含氮杂质。具体地,所述基于多硫醇化合物的总重量,所述多硫醇化合物可以包括5-8wt%的含氮杂质。此外,所述含氮杂质可以是选自三聚氰胺、脲、三嗪、酰胺、酰亚胺或亚胺中的一种或多种。
所述异氰酸酯化合物可以是通常用于合成聚硫代氨基甲酸酯的化合物。具体地,所述异氰酸酯化合物可以包括选自由脂肪族异氰酸酯化合物(例如异佛尔酮二异氰酸酯、二环己基甲烷-4,4-二异氰酸酯、六亚甲基二异氰酸酯、2,2-二甲基戊二异氰酸酯、2,2,4-三甲基己二异氰酸酯、丁烯二异氰酸酯、1,3-丁二烯-1,4-二异氰酸酯、2,4,4-三甲基六亚甲基二异氰酸酯、1,6,11-十一烷三异氰酸酯、1,3,6-六亚甲基三异氰酸酯、1,8-二异氰氧基-4-异氰氧基甲基辛烷、双(异氰氧基乙基)碳酸酯、双(异氰氧基乙基)醚等)、脂环族异氰酸酯化合物(例如异佛尔酮二异氰酸酯、1,2-双(异氰氧基甲基)环己烷、1,3-双(异氰氧基甲基)环己烷、1,4-双(异氰氧基甲基)环己烷、二环己基甲烷二异氰酸酯、环己烷二异氰酸酯、甲基环己烷二异氰酸酯、二环己基二甲基甲烷异氰酸酯、2,2-二甲基二环己基甲烷异氰酸酯等)、芳香族异氰酸酯化合物(例如双(异氰氧基乙基)苯、双(异氰氧基丙基)苯、双(异氰氧基丁基)苯、双(异氰氧基甲基)萘、双(异氰氧基甲基)二苯基醚、苯叉基二异氰酸酯、乙基苯叉基二异氰酸酯、异丙基苯叉基二异氰酸酯、二甲基苯叉基二异氰酸酯、二乙基苯叉基二异氰酸酯、二异丙基苯叉基二异氰酸酯、三甲基苯三异氰酸酯、苯三异硫氰酸酯、联苯二异氰酸酯、甲苯胺二异氰酸酯、4,4-二苯基甲烷二异氰酸酯、3,3-二甲基二苯基甲烷-4,4-二异氰酸酯、二苄基-4,4-二异氰酸酯、双(异氰氧基苯基)乙烯、3,3-二甲氧基联苯基-4,4-二异氰酸酯、六氢苯二异氰酸酯、六氢二苯甲烷-4,4-二异氰酸酯、邻二甲苯二异氰酸酯、间二甲苯二异氰酸酯、对二甲苯二异氰酸酯等)、含硫的脂肪族多异氰酸酯化合物(例如双(异氰氧基乙基)硫醚、双(异氰氧基丙基)硫醚、双(异氰氧基己基)硫醚、双(异氰氧基甲基)砜、双(异氰氧基甲基)二硫醚、双(异氰氧基丙基)二硫醚、双(异氰氧基甲硫基)甲烷、双(异氰氧基乙硫基)甲烷、双(异氰氧基乙硫基)乙烷、双(异氰氧基甲硫基)乙烷、1,5-二异氰氧基-2-异氰氧基甲基-3-硫杂戊烷等)、含硫的芳香族多异氰酸酯化合物(例如二苯基硫醚-2,4-二异氰酸酯、二苯基硫醚-4,4-二异氰酸酯、3,3-二甲氧基-4,4-二异氰氧基二苄基硫醚、双(4-异氰氧基甲基苯基)硫醚、4,4-甲氧基苯硫代乙二醇-3,3-二异氰酸酯、二苯基二硫醚-4,4-二异氰酸酯、2,2-二甲基二苯基二硫醚-5,5-二异氰酸酯、3,3-二甲基二苯基二硫醚-5,5-二异氰酸酯、3,3-二甲基二苯基二硫醚-6,6-二异氰酸酯、4,4-二甲基二苯基二硫醚-5,5-二异氰酸酯、3,3-二甲基二苯基二硫醚-4,4-二异氰酸酯等)、含硫的杂环异氰酸酯化合物(例如2,5-二异氰氧基噻吩、2,5-双(异氰氧基甲基)噻吩、2,5-二异氰氧基四氢噻吩、2,5-双(异氰氧基甲基)四氢噻吩、3,4-双(异氰氧基甲基)四氢噻吩、2,5-二异氰氧基-1,4-二噻烷、2,5-双(异氰氧基甲基)-1,4-二噻烷、4,5-二异氰氧基-1,3-二硫戊环、4,5-双(异氰氧基甲基)-1,3-二硫戊环、4,5-双(异氰氧基甲基)-2-甲基-1,3-二硫戊环等)组成的群中的一种或多种。
所述聚合性组合物可以包括当量比为0.5-1.5:1的多硫醇化合物和异氰酸酯化合物。具体地,所述聚合性组合物可以包括当量比为0.8-1.2:1的多硫醇化合物和异氰酸酯化合物。
根据需要,所述酸组分可以与所述多硫醇化合物或异氰酸酯化合物预混合。
在25℃下放置8小时后,所述聚合性组合物可以表现出1000cPs(厘泊)以下的粘度(25℃)。具体地,在25℃下放置8小时后,所述聚合性组合物可以表现出700cPs以下的粘度(25℃),或200-700cPs的粘度(25℃)。
根据另一个实施方式的所述聚合性组合物可以进一步包括添加剂,例如内部脱模剂、反应催化剂、热稳定剂、紫外吸收剂或上蓝剂等,这取决于其目的。
可以使用二苯甲酮、苯并三唑、水杨酸酯、氰基丙烯酸酯、草酰苯胺类化合物等,作为紫外吸收剂。此外,所述内部脱模剂可以选自:具有全氟烷基、羟烷基或磷酸酯基的氟类非离子表面活性剂;具有二甲基聚硅氧烷基、羟烷基或磷酸酯基的有机硅类非离子表面活性剂;烷基季铵盐,例如三甲基鲸蜡基铵盐、三甲基硬脂基铵盐、二甲基乙基鲸蜡基铵盐、三乙基十二烷基铵盐、三辛基甲基铵盐,或二乙基环己基十二烷基铵盐等;以及酸性磷酸酯。它们可以单独使用,或者以两种以上的组合使用。
所述反应催化剂可以是已知的能用于制备聚硫代氨基甲酸酯类化合物的反应催化剂。具体地,二烷基卤化锡,例如二丁基二氯化锡、二甲基二氯化锡等;二羧酸二烷基锡,例如,二乙酸二甲基锡、二辛酸二丁基锡、二月桂酸二丁基锡等;二烷氧基二烷基锡烷,例如二丁氧基二丁基锡烷、二丁氧基二辛基锡烷等;二硫代烷氧基二烷基锡烷,例如二硫代丁氧基二丁基锡烷等;二烷基氧化锡,例如二(2-乙基己基)氧化锡、二辛基氧化锡、双(丁氧基二丁基锡)氧化物等;以及二烷基硫化锡,例如二丁基硫化锡等,可以用作反应催化剂。更具体地,诸如二丁基二氯化锡、二甲基二氯化锡等的二烷基卤化锡,可以用作反应催化剂。
所述上蓝剂在可见光区域具有从橙色到黄色的波长范围内的吸收带,并且具有调节由树脂制构成的光学材料的颜色的功能。具体地,所述上蓝剂可以包括呈蓝色至紫色的材料,但并不特别限于此。此外,所述上蓝剂可以为染料、荧光增白剂、荧光颜料和无机颜料等,且可根据最终光学产品所需的物理性能或树脂颜色来适当地选择它。每种上蓝剂可以单独使用,或者以两种以上的组合使用。考虑到在所述聚合性组合物中的溶解性和光学材料的透明度,上蓝剂理想地为染料。从吸收波长的角度看,该染料可以具有520-600nm的最大吸收波长;更具体地,可以具有540-580nm的最大吸收波长。另外,就化合物的结构而言,该染料理想地为蒽醌类染料。添加上蓝剂的方法没有特别限制,可以预先将上蓝剂添加到单体体系中。具体地,可以使用各种方法来添加上蓝剂;例如,将上蓝剂溶解在单体中的方法,或者制备含有高浓度上蓝剂的母液,然后用单体或其他添加剂稀释该母溶液的方法。
另一个实施方式提供了由如上所述的这种聚合性组合物获得的聚硫代氨基甲酸酯类化合物。
聚硫代氨基甲酸酯类化合物是通过将聚硫醇化合物和异氰酸酯化合物进行聚合(及固化)来制备。如上所述,在聚合期间,添加到所述聚合性组合物中的酸组分与多硫醇化合物中存在的杂质形成盐,以适当地调节异氰酸酯化合物的反应性,从而促进聚硫代氨基甲酸酯类化合物的有效合成。
在聚合反应中,SH基团/NCO基团的反应摩尔比可以为0.5至3.0,特别地可以为0.8至1.3。
此外,为了调节反应速率,可以加入通常用于制备聚硫代氨基甲酸酯的反应催化剂。可以使用锡类催化剂作为反应催化剂,并且,例如,可以使用二丁基二氯化锡、二月桂酸二丁基锡、二甲基二氯化锡等。
另一个实施方式提供了由如上所述的这种聚硫代氨基甲酸酯类化合物模塑而成的光学材料。
也就是说,光学材料可以通过聚合和模塑聚合性组合物(包含多硫醇化合物、异氰酸酯化合物和酸组分)来制备。
首先,在将所述聚合性组合物在减压下脱气后,将其注入到模具中以模塑光学材料。这种脱气和注塑可以在20-40℃的温度范围下进行。在注入到模具后,通常通过从低温到高温的逐渐加热来进行聚合。
该聚合反应的温度可以是30-150℃,更具体地,可以是40-130℃。此外,为了调节反应速率,可以加入通常用于制备聚硫代氨基甲酸酯的反应催化剂,其例子如上所述。
然后,将聚硫代氨基甲酸酯类光学材料从模具中取出。
通过改变待使用的模具,可以制备各种形状的光学材料。具体地,所述光学材料可以是眼镜镜片、相机镜头或发光二极管(LED)等形式。
当测量光学材料的色坐标时,光学材料可具有6以下的黄度指数。黄度指数越低,光学材料的颜色越好,黄度指数越高,颜色越差。黄度指数值是通过测量平均厚度为9mm且平均直径为75mm的圆形光学材料获得,并且它可以是将通过采用Minolta CM-5色差计测量的色度坐标x和y应用到下面的数学公式1而计算出的值。
[数学公式1]
黄度指数=(234x+106y+106)/y
所述光学材料可以理想地是光学镜片,特别是塑料光学镜片。
因此,根据一个实施方式,包含特定添加剂的聚合性组合物,可以适当地调节异氰酸酯的反应性,使得在预定的时间段内保持较低的粘度,因此,能够制备高质量的聚硫代氨基甲酸酯类光学材料,甚至不需要复杂的纯化过程。而且,根据另一实施方式的聚硫代氨基甲酸酯类光学材料不仅具有均匀的折射率,而且具有低的黄度指数,因此可以用作各种塑料光学镜片,例如眼镜镜片或相机镜头等。
本发明的方式
以下,通过实施例详细说明本发明。以下实施例旨在进一步说明本发明实施方式而不限制其范围。
实施例1
将50.7重量份的间二甲苯二异氰酸酯、0.01重量份的作为固化催化剂的二丁基二氯化锡、0.1重量份的内部脱模剂(制造商:Stepan,产品名称:UN,酸性烷基磷酸酯脱模剂)、0.05重量份的紫外吸收剂(2-(2'-羟基-5'-叔辛基苯基)-2H-苯并三唑,制造商:Cytec,产品名称:UV-5411)和0.5重量份的磷酸在25℃下混合得到混合物,向该混合物中加入49.3重量份的多硫醇B,然后再次均匀混合,制得聚合性组合物。
多硫醇B是由下式1表示的双(2-(2-巯基乙硫基)-3-巯基丙基)硫醚,并且在以下测量条件下的HPLC测量出显示出高含量的含氮化合物,且含氮化合物(B)的峰面积/多硫醇化合物(A)的峰面积为7.8%。
此外,多硫醇B的电感耦合等离子体(ICP)分析结果表明,多硫醇B包含1.4ppm的Ca、1.6ppm的Mg、1.9ppm的K和2.1ppm的Na。
[式1]
<HPLC测量条件>
柱子:YMC-Pack ODS-A A-312(S5,直径6mm×高150mm)
流动相:乙腈/0.01mol的磷酸二氢钾水溶液=60/40(v/v)
流速:1.0mL/min
检测器:紫外检测器,波长230nm
测量溶液的制备:将160mg的样品溶解并混合于10mL的乙腈中
测量溶液的注入量:2μL。
实施例2-4及比较例1-3
除了使用如下表1中所示的组分和含量(重量份)之外,采用与实施例1相同的方法制备聚合性组合物。
[表1]
多硫醇A是由上式1表示的双(2-(2-巯基乙硫基)-3-巯基丙基)硫醚,并且在与实施例1相同的条件下的HPLC测量显示B/A百分比为1.9%。此外,ICP分析显示,多硫醇A包含1.0ppm的Ca、1.1ppm的Mg、1.2ppm的K和1.7ppm的Na。
多硫醇C是由上式1表示的双(2-(2-巯基乙硫基)-3-巯基丙基)硫醚,并且在与实施例1相同的测量条件下的HPLC测量显示B/A百分比为2.8%。此外,ICP分析显示,多硫醇C包含1.3ppm的Ca、1.7ppm的Mg、1.8ppm的K和621ppm的Na、高Na阳离子含量。
实验例:物理性能的测量
如下所示,测量实施例1-4和比较例1-3中制备的聚合性组合物的物理性能,测量结果示于下表2中。
(1)粘度
在将聚合性组合物在25℃下放置8小时后,使用旋转粘度计在25℃下测量粘度。
(2)黄度指数和耐光性(ΔYI)
将实施例1-4和比较例1-3中制备的聚合性组合物在600Pa下脱气1小时,然后在3μm特氟龙过滤器中过滤。将过滤后的聚合性组合物注入到由胶带组装的玻璃模具中。以5℃/分钟的速率将模具的温度从25℃升至120℃,并在120℃下进行聚合18小时。将在玻璃模具中固化的树脂在130℃下进一步固化4小时,然后从模具中取出模塑制品。
该模塑制品是厚度为9mm、直径为75mm的圆形镜片(光学材料),将通过采用Minolta CM-5色差计测量的色度坐标x和y应用到下面的数学公式1而计算得到光学材料的黄度指数(YI)。
[数学公式1]
黄度指数=(234x+106y+106)/y
在将光学材料暴露于Q-Panel Lab Products公司的型号为QUV/Spray(5w)的设备200小时后,使用与上述相同的方法测量其黄度指数。然后,将曝光前后的黄度指数值的差异以耐光性(ΔYI)显示。
[表2]
如表2所示,当将实施例1-4的聚合性组合物与比较例1-3的聚合性组合物进行比较时,实施例1-4的聚合性组合物的粘度在相对长的时间内保持较低,且由这些聚合性组合物模塑成的镜片显示出低的黄度指数和优异的耐光性(ΔYI),因此可以看出实施例1-4的聚合性组合物更适合作为光学材料。特别地,可以在使用相同多硫醇(相同杂质含量)的聚合性组合物之间进行直接比较,即在实施例1和比较例1之间,实施例2和比较例2之间,以及实施例3和比较例3之间。
Claims (12)
1.一种聚合性组合物,包括:
(i)多硫醇化合物;
(ii)异氰酸酯化合物;以及
(iii)酸组分,所述酸组分包括一价至四价的羧酸、磷酸或其混合,所述羧酸是选自由油酸、草酸、棕榈油酸、亚油酸、丙二酸和丁二酸组成的群中的一种或多种;
(iv)锡基催化剂;
其中,相对于100重量份的所述多硫醇化合物和所述异氰酸酯化合物的总和,所述聚合性组合物包括量为0.1-1重量份的所述酸组分。
2.如权利要求1所述的聚合性组合物,其特征在于,相对于100重量份的多硫醇化合物和异氰酸酯化合物的总和,所述聚合性组合物包括量为0.1-1重量份的油酸、草酸或磷酸。
3.如权利要求1所述的聚合性组合物,其特征在于,在25℃下放置8小时后,所述聚合性组合物显示出1000cPs以下的粘度。
4.如权利要求1所述的聚合性组合物,其特征在于,所述多硫醇化合物包括金属阳离子杂质、含氮杂质或其混合。
5.如权利要求4所述的聚合性组合物,其特征在于,所述多硫醇化合物包括100至6000ppm的所述金属阳离子杂质。
6.如权利要求4所述的聚合性组合物,其特征在于,所述金属阳离子杂质是选自由Ca阳离子、Mg阳离子、K阳离子和Na阳离子组成的群中的一种或多种。
7.如权利要求4所述的聚合性组合物,其特征在于,基于所述多硫醇化合物的总重量,所述多硫醇化合物包括3-10wt%的含氮杂质。
8.如权利要求4所述的聚合性组合物,其特征在于,所述含氮杂质是选自由三聚氰胺、脲、三嗪、酰胺、酰亚胺和亚胺组成的群中的一种或多种。
9.由权利要求1-8中任一项所述的聚合性组合物得到的聚硫代氨基甲酸酯类化合物。
10.由权利要求9所述的聚硫代氨基甲酸酯类化合物模塑而成的光学材料。
11.如权利要求10所述的光学材料,其特征在于,所述光学材料为塑料光学镜片。
12.如权利要求10所述的光学材料,其特征在于,当测量色度坐标时,所述光学材料的黄度指数为6以下。
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