CN113166311B - 光学材料用组合物和光学材料 - Google Patents
光学材料用组合物和光学材料 Download PDFInfo
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- CN113166311B CN113166311B CN201980082234.6A CN201980082234A CN113166311B CN 113166311 B CN113166311 B CN 113166311B CN 201980082234 A CN201980082234 A CN 201980082234A CN 113166311 B CN113166311 B CN 113166311B
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- 125000000217 alkyl group Chemical group 0.000 claims description 22
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- 125000003545 alkoxy group Chemical group 0.000 claims description 11
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- ZDKYYMRLZONTFK-UHFFFAOYSA-N 3,4-bis(isocyanatomethyl)bicyclo[2.2.1]heptane Chemical compound C1CC2(CN=C=O)C(CN=C=O)CC1C2 ZDKYYMRLZONTFK-UHFFFAOYSA-N 0.000 claims description 6
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- NXYWIOFCVGCOCB-UHFFFAOYSA-N 3-(2-sulfanylethylsulfanyl)-2-[3-sulfanyl-2-(2-sulfanylethylsulfanyl)propyl]sulfanylpropane-1-thiol Chemical compound SCCSCC(CS)SCC(CS)SCCS NXYWIOFCVGCOCB-UHFFFAOYSA-N 0.000 claims description 3
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- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
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- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 1
- XSROQCDVUIHRSI-UHFFFAOYSA-N thietane Chemical compound C1CSC1 XSROQCDVUIHRSI-UHFFFAOYSA-N 0.000 description 1
- 125000002053 thietanyl group Chemical group 0.000 description 1
- UVZICZIVKIMRNE-UHFFFAOYSA-N thiodiacetic acid Chemical compound OC(=O)CSCC(O)=O UVZICZIVKIMRNE-UHFFFAOYSA-N 0.000 description 1
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- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
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- 239000013638 trimer Substances 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- JQPMDTQDAXRDGS-UHFFFAOYSA-N triphenylalumane Chemical compound C1=CC=CC=C1[Al](C=1C=CC=CC=1)C1=CC=CC=C1 JQPMDTQDAXRDGS-UHFFFAOYSA-N 0.000 description 1
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- KCTAHLRCZMOTKM-UHFFFAOYSA-N tripropylphosphane Chemical compound CCCP(CCC)CCC KCTAHLRCZMOTKM-UHFFFAOYSA-N 0.000 description 1
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Abstract
本发明为一种光学材料用组合物以及含有该组合物的光学材料,所述光学材料用组合物的特征在于,含有(A)聚合性单体100质量份、和(B)极大吸收波长为360nm以上且小于380nm的具有特定结构的紫外线吸收剂0.001~0.3质量份。根据本发明,可以提供长期保存稳定性良好的含有紫外线吸收剂的光学材料用组合物及含有其的光学材料,特别是可以提供能够形成对蓝光的阻挡率高的塑料透镜的光学材料用组合物。
Description
技术领域
本发明提供含有长期保存稳定性良好的紫外线吸收剂的光学材料用组合物和含有其的光学材料,特别是提供可形成蓝光的阻挡率高的塑料透镜的光学材料用组合物。
背景技术
一直以来,眼睛暴露于紫外线所带来的不良影响被视为问题。此外,近年来,据说对眼睛健康的蓝色区域(380~500nm)的光线(以下也称为蓝光)的能量也强,因而对视网膜等造成损伤。由蓝光引起的损害被称为“蓝光危害”,为了防止这种损害,据说特别希望阻挡较短波长的380~420nm左右的蓝光。
为了解决这样的问题,例如,专利文献1中提出了具备在塑料部件的凸面上配设的多层膜、该多层膜对400~500nm的波长范围的平均反射率为2~10%的透镜。但是,当对该透镜测定蓝光阻挡率时,为30%左右。
另外,专利文献2、3中记载了含有苯并***系紫外线吸收剂、提高光线阻挡率的透镜用聚合性组合物,但它们只着眼于405nm以下的吸收,没有关于蓝光阻挡率的任何讨论。
另外,专利文献4、5中提出了含有2-(2-羟基-3-叔丁基-5-甲基苯基)-氯苯并***紫外线吸收剂、提高蓝光阻挡率的透镜用聚合性组合物,但该紫外线吸收剂在单体中的溶解度低,因此长期保存稳定性差。
现有技术文献
专利文献
专利文献1:日本特开2012-093689号公报
专利文献2:日本特开2008-056854号公报
专利文献3:日本特开2010-84006号公报
专利文献4:日本专利5620033号公报
专利文献5:日本专利6294386号公报
发明内容
发明要解决的课题
因此,本发明的目的在于,提供长期保存稳定性良好的光学材料用组合物和含有其的光学材料,特别是提供能够形成对蓝光的阻挡率高的塑料透镜的光学材料用组合物。
解决课题的手段
本发明人等为了达成上述目的进行了深入研究,结果发现,通过使用极大吸收波长为360nm以上且小于380nm的含有特定结构的苯并***化合物的紫外线吸收剂,可达成上述目的,至此完成了本发明。
即,本发明涉及如下内容:
[1]光学材料用组合物,其特征在于,含有(A)聚合性单体100质量份、和(B)极大吸收波长为360nm以上且小于380nm的下述式(1)表示的紫外线吸收剂0.001~0.3质量份。
[化1]
(其中,R1表示氢原子、碳数1~8的烷基、碳数1~8的烷氧基、羟基、碳数1~4的直链或支链的单取代氨基、碳数1~4的直链或支链的二取代氨基、硝基、羧基、烷基的碳数为1~8的烷氧羰基、碳数1~8的羟基烷基、烷基的碳数各自为1~8的烷基羰氧基烷基、烷基的碳数为1~3的羧基烷基、烷基的碳数合计为2~10的烷氧羰基烷基、芳基、酰基、磺基或氰基;
R2表示羟基、碳数1~8的烷氧基、碳数1~8的烷硫基、碳数1~4的直链或支链的单取代氨基、碳数1~4的直链或支链的二取代氨基;
R3表示氢原子、羟基、碳数1~8的烷基或烷氧基、碳数1~4的直链或支链的单取代氨基、碳数1~4的直链或支链的二取代氨基,
也可以是R2和R3交联的环状结构。)
本发明可采用以下实施方式。
[2]上述[1]所述的光学材料用组合物,其中,上述聚合性单体(A)含有:
选自双(异氰酸酯基甲基)双环[2.2.1]庚烷、苯二甲基二异氰酸酯、4,4′-亚甲基二苯基二异氰酸酯、2,4′-亚甲基二苯基二异氰酸酯和甲基-1,3-亚苯基二异氰酸酯中的至少1种多异氰酸酯化合物,以及
选自季戊四醇四(3-巯基丙酸)酯和1,2-双(2-巯基乙硫基)-3-巯基丙烷中的至少1种多硫醇化合物。
[3]上述[1]所述的光学材料用组合物,其中,上述聚合性单体(A)含有:
双(2,3-环硫丙基)二硫醚,以及
以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和4,8-二巯基甲基-1,11-二巯基-3,6,9-三硫杂十一烷为主成分的混合物。
[4]光学材料,其是含有由上述[1]~[3]任一项所述的光学材料用组合物聚合固化而成的固化物的光学材料,其中,波长400nm的光线透射率为5%以下且波长420nm的光线透射率为70%以下,且380~500nm的波长区域的光线阻挡率为35%以上。
[5]塑料透镜,其含有上述[4]所述的光学材料。
予以说明,本发明中,各化合物的极大吸收波长等的测定是在不影响该测定的溶剂中进行的。作为该溶剂,例如可举出氯仿。
发明效果
通过将本发明的光学材料用组合物聚合固化,能够得到蓝光的阻挡率高的光学材料、特别是含有该光学材料的塑料透镜,另外,由于该组合物的保存稳定性良好,因而其利用价值高。
具体实施方式
本发明的光学材料用组合物的特征在于,含有:
(A)聚合性单体100质量份,和
(B)极大吸收波长为360nm以上且小于380nm,且具有特定结构的紫外线吸收剂0.001~0.3质量份。
以下,说明各成分。
<(A)成分:聚合性单体>
本发明中,可使用公知的聚合性单体。
作为可适用于光学材料用组合物的聚合性单体,可使用公知的加聚系单体(以下有时也简称为“(A1)成分”)、阳离子聚合性单体(以下有时也简称为“(A2)成分”)和自由基聚合性单体(以下有时也简称为“(A3)成分”)。
<(A1)加聚系聚合性单体>
本发明的加聚系聚合性单体可不受特别限制地使用公知的单体,例如为:作为用于得到聚氨酯树脂、聚硫氨酯树脂、聚脲树脂、聚氨酯-聚脲树脂、聚硫氨酯-聚脲树脂等树脂的原料的单体。具体地,可分别通过以下组合的形式来使用:多异氰酸酯化合物与多元醇化合物的组合;多异氰酸酯化合物与多硫醇化合物的组合;多异氰酸酯化合物与多胺化合物的组合;多异氰酸酯化合物、多元醇化合物与多胺化合物的组合;多异氰酸酯化合物、多硫醇化合物与多胺化合物的组合,这些单体的组合可单独使用或混合使用。
以下,详细说明加聚系聚合性单体。
<(A1-1)多异氰酸酯化合物>
作为上述多异氰酸酯化合物(以下有时也简称为(A1-1)成分),没有特别限定,作为其具体例,可举出:双(异氰酸酯基甲基)环己烷、双(异氰酸酯基甲基)双环[2.2.1]庚烷、氢化2,6-甲苯二异氰酸酯、氢化间苯二异氰酸酯、氢化对苯二异氰酸酯、氢化2,4-甲苯二异氰酸酯、氢化二苯基甲烷二异氰酸酯、氢化间苯二甲基二异氰酸酯、氢化对苯二甲基二异氰酸酯、异佛尔酮二异氰酸酯等脂环族异氰酸酯化合物;苯二异氰酸酯、甲苯二异氰酸酯、二苯基甲烷二异氰酸酯、苯二甲基二异氰酸酯、四甲基苯二甲基二异氰酸酯、2,6-萘二异氰酸酯、1,5-萘二异氰酸酯等芳族异氰酸酯化合物;六亚甲基二异氰酸酯、八亚甲基二异氰酸酯、2,2,4-三甲基六亚甲基二异氰酸酯、四亚甲基二异氰酸酯、六亚甲基二异氰酸酯的缩二脲反应产物、六亚甲基二异氰酸酯的三聚体、赖氨酸二异氰酸酯、赖氨酸三异氰酸酯、1,6,11-十一烷三异氰酸酯、三苯基甲烷三异氰酸酯等不具有脂环或芳环的异氰酸酯化合物;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′-二甲氧基二苯基二硫醚-4,4′-二异氰酸酯、4,4′-二甲氧基二苯基二硫醚-3,3′-二异氰酸酯、二苯基砜-4,4′-二异氰酸酯、二苯基砜-3,3′-二异氰酸酯、亚苄基砜-4,4′-二异氰酸酯、二苯基甲烷砜-4,4′-二异氰酸酯、4-甲基二苯基甲烷砜-2,4′-二异氰酸酯、4,4′-二甲氧基二苯基砜-3,3′-二异氰酸酯、3,3′-二甲氧基-4,4′-二异氰酸根合二苄基砜、4,4′-二甲基二苯基砜-3,3′-二异氰酸酯、4,4′-二叔丁基二苯基砜-3,3′-二异氰酸酯、4,4′-二甲氧基苯乙烯二砜-3,3′-二异氰酸酯、4,4′-二氯二苯基砜-3,3′-二异氰酸酯、4-甲基-3-异氰酸根合苯磺酰基-4′-异氰酸根合苯酚酯、4-甲氧基-3-异氰酸根合苯磺酰基-4′-异氰酸根合苯酚酯、4-甲基-3-异氰酸根合苯磺酰苯胺-3'-甲基-4′-异氰酸酯、二苯磺酰基-亚乙基二胺-4,4′-二异氰酸酯、4,4′-二甲氧基苯磺酰基-亚乙基二胺-3,3′-二异氰酸酯、4-甲基-3-异氰酸根合苯磺酰苯胺-4-甲基-3′-异氰酸酯、噻吩-2,5-二异氰酸酯、噻吩-2,5-二异氰酸甲酯、1,4-二噻烷-2,5-二异氰酸酯、1,4-二噻烷-2,5-二异氰酸甲酯、1,4-二噻烷-2,3-二异氰酸甲酯、1,4-二噻烷-2-异氰酸根合甲基-5-异氰酸丙酯、1,3-二硫杂环戊烷-4,5-二异氰酸酯、1,3-二硫杂环戊烷-4,5-二异氰酸甲酯、1,3-二硫杂环戊烷-2-甲基-4,5-二异氰酸甲酯、1,3-二硫杂环戊烷-2,2-二异氰酸乙酯、四氢噻吩-2,5-二异氰酸酯、四氢噻吩-2,5-二异氰酸甲酯、四氢噻吩-2,5-二异氰酸乙酯、四氢噻吩-3,4-二异氰酸甲酯等含有硫的异氰酸酯化合物。其中,优选为脂环族异氰酸酯化合物。
<(A1-2)多硫醇化合物>
作为上述多硫醇化合物(以下有时也简称为(A1-2)成分),可举出:甲二硫醇、1,2-乙二硫醇、1,1-丙二硫醇、1,2-丙二硫醇、1,3-丙二硫醇、2,2-丙二硫醇、1,6-己二硫醇、1,2,3-丙三硫醇、四(巯基甲基)甲烷、1,1-环己二硫醇、1,2-环己二硫醇、2,2-二甲基丙烷-1,3-二硫醇、3,4-二甲氧基丁烷-1,2-二硫醇、2-甲基环己烷-2,3-二硫醇、1,1-双(巯基甲基)环己烷、硫代苹果酸双(2-巯基乙酯)、2,3-二巯基琥珀酸(2-巯基乙酯)、2,3-二巯基-1-丙醇(2-巯基乙酸酯)、2,3-二巯基-1-丙醇(3-巯基乙酸酯)、二甘醇双(2-巯基乙酸酯)、二甘醇双(3-巯基丙酸酯)、1,2-二巯基丙基甲基醚、2,3-二巯基丙基甲基醚、2,2-双(巯基甲基)-1,3-丙二硫醇、双(2-巯基乙基)醚、乙二醇双(2-巯基乙酸酯)、乙二醇双(3-巯基丙酸酯)、三羟甲基丙烷三(2-巯基乙酸酯)、三羟甲基丙烷三(3-巯基丙酸酯)、季戊四醇四(2-巯基乙酸)酯、季戊四醇四(3-巯基丙酸)酯、1,2-双(2-巯基乙硫基)-3-巯基丙烷等脂族硫醇;1,2-二巯基苯、1,3-二巯基苯、1,4-二巯基苯、1,2-双(巯基甲基)苯、1,3-双(巯基甲基)苯、1,4-双(巯基甲基)苯、1,3-双(巯基乙基)苯、1,4-双(巯基乙基)苯、1,2-双(巯基甲氧基)苯、1,3-双(巯基甲氧基)苯、1,4-双(巯基甲氧基)苯、1,2-双(巯基乙氧基)苯、1,3-双(巯基乙氧基)苯、1,4-双(巯基乙氧基)苯、1,2,3-三巯基苯、1,2,4-三巯基苯、1,3,5-三巯基苯、1,2,3-三(巯基甲基)苯、1,2,4-三(巯基甲基)苯、1,3,5-三(巯基甲基)苯、1,2,3-三(巯基乙基)苯、1,2,4-三(巯基乙基)苯、1,3,5-三(巯基乙基)苯、1,2,3-三(巯基甲氧基)苯、1,2,4-三(巯基甲氧基)苯、1,3,5-三(巯基甲氧基)苯、1,2,3-三(巯基乙氧基)苯、1,2,4-三(巯基乙氧基)苯、1,3,5-三(巯基乙氧基)苯、1,2,3,4-四巯基苯、1,2,3,5-四巯基苯、1,2,4,5-四巯基苯、1,2,3,4-四(巯基甲基)苯、1,2,3,5-四(巯基甲基)苯、1,2,4,5-四(巯基甲基)苯、1,2,3,4-四(巯基乙基)苯、1,2,3,5-四(巯基乙基)苯、1,2,4,5-四(巯基乙基)苯、1,2,3,4-四(巯基乙基)苯、1,2,3,5-四(巯基甲氧基)苯、1,2,4,5-四(巯基甲氧基)苯、1,2,3,4-四(巯基乙氧基)苯、1,2,3,5-四(巯基乙氧基)苯、1,2,4,5-四(巯基乙氧基)苯、2,2′-二巯基联苯、4,4′-二巯基联苯、4,4′-二巯基联苄、2,5-甲苯二硫醇、3,4-甲苯二硫醇、1,4-萘二硫醇、1,5-萘二硫醇、2,6-萘二硫醇、2,7-萘二硫醇、2,4-二甲基苯-1,3-二硫醇、4,5-二甲基苯-1,3-二硫醇、9,10-蒽二甲烷硫醇、1,3-二(对甲氧基苯基)丙烷-2,2-二硫醇、1,3-二苯基丙烷-2,2-二硫醇、苯基甲烷-1,1-二硫醇、2,4-二(对巯基苯基)戊烷等芳族硫醇;2,5-二氯苯-1,3-二硫醇、1,3-二(对氯苯基)丙烷-2,2-二硫醇、3,4,5-三溴-1,2-二巯基苯、2,3,4,6-四氯-1,5-双(巯基甲基)苯等盐素取代体、溴取代体等卤素取代的芳族硫醇;1,2-双(巯基甲硫基)苯、1,3-双(巯基甲硫基)苯、1,4-双(巯基甲硫基)苯、1,2-双(巯基乙硫基)苯、1,3-双(巯基乙硫基)苯、1,4-双(巯基乙硫基)苯、1,2,3-三(巯基甲硫基)苯、1,2,4-三(巯基甲硫基)苯、1,3,5-三(巯基甲硫基)苯、1,2,3-三(巯基乙硫基)苯、1,2,4-三(巯基乙硫基)苯、1,3,5-三(巯基乙硫基)苯、1,2,3,4-四(巯基甲硫基)苯、1,2,3,5-四(巯基甲硫基)苯、1,2,4,5-四(巯基甲硫基)苯、1,2,3,4-四(巯基乙硫基)苯、1,2,3,5-四(巯基乙硫基)苯、1,2,4,5-四(巯基乙硫基)苯等、以及它们的烷基化物等除了巯基以外还含有硫原子的芳族硫醇;双(巯基甲基)硫醚、双(巯基乙基)硫醚、双(巯基丙基)硫醚、双(巯基甲硫基)甲烷、双(2-巯基乙硫基)甲烷、双(3-巯基丙硫基)甲烷、1,2-双(巯基甲硫基)乙烷、1,2-双(2-巯基乙硫基)乙烷、1,2-双(3-巯基丙硫基)乙烷、1,3-双(巯基甲硫基)丙烷、1,3-双(2-巯基乙硫基)丙烷、1,3-双(3-巯基丙硫基)丙烷、1,2-双(2-巯基乙硫基)-3-巯基丙烷、2-巯基乙硫基-1,3-丙二硫醇、1,2,3-三(巯基甲硫基)丙烷、1,2,3-三(2-巯基乙硫基)丙烷、1,2,3-三(3-巯基丙硫基)丙烷、四(巯基甲硫基甲基)甲烷、四(2-巯基乙硫基甲基)甲烷、四(3-巯基丙硫基甲基)甲烷、双(2,3-二巯基丙基)硫醚、2,5-二巯基-1,4-二噻烷、双(巯基甲基)二硫醚、双(巯基乙基)二硫醚、双(巯基丙基)二硫醚等、以及它们的巯基乙酸酯和巯基丙酸酯、羟甲基硫醚双(2-巯基乙酸酯)、羟甲基硫醚双(3-巯基丙酸酯)、羟乙基硫醚双(2-巯基乙酸酯)、羟乙基硫醚双(3-巯基丙酸酯)、羟丙基硫醚双(2-巯基乙酸酯)、羟丙基硫醚双(3-巯基丙酸酯)、羟甲基二硫醚双(2-巯基乙酸酯)、羟甲基二硫醚双(3-巯基丙酸酯)、羟乙基二硫醚双(2-巯基乙酸酯)、羟乙基二硫醚双(3-巯基丙酸酯)、羟丙基二硫醚双(2-巯基乙酸酯)、羟丙基二硫醚双(3-巯基丙酸酯)、2-巯基乙基醚双(2-巯基乙酸酯)、2-巯基乙基醚双(3-巯基丙酸酯)、1,4-二噻烷-2,5-二醇双(2-巯基乙酸酯)、1,4-二噻烷-2,5-二醇双(3-巯基丙酸酯)、巯基乙酸(2-巯基乙酯)、硫代二丙酸双(2-巯基乙酯)、4,4′-硫代二丁酸双(2-巯基乙酯)、亚二硫基二乙酸双(2-巯基乙酯)、二硫代二丙酸双(2-巯基乙酯)、4,4′-二硫代二丁酸双(2-巯基乙酯)、亚硫基二乙酸双(2,3-二巯基丙酯)、硫代二丙酸双(2,3-二巯基丙酯)、亚二硫基二乙酸双(2,3-二巯基丙酯)、二硫代二丙酸双(2,3-二巯基丙酯)、4-巯基甲基-3,6-二硫杂辛烷-1,8-二硫醇、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、双(1,3-二巯基-2-丙基)硫醚等除了巯基以外还含有硫原子的脂族硫醇;3,4-噻吩二硫醇、2,5-二巯基甲基-四氢噻吩、2,5-二巯基-1,3,4-噻二唑、2,5-二巯基-1,4-二噻烷、2,5-二巯基甲基-1,4-二噻烷等除了巯基以外还含有硫原子的杂环化合物等。
<(A1-3)多元醇化合物>
作为上述多元醇化合物(以下有时也简称为(A1-3)成分),例如可举出:乙二醇、二甘醇、丙二醇、二丙二醇、丁二醇、新戊二醇、甘油、三羟甲基乙烷、三羟甲基丙烷、丁三醇、1,2-甲基葡糖苷、季戊四醇、二季戊四醇、三季戊四醇、三甘醇、聚乙二醇、三(2-羟乙基)异氰尿酸酯、环丁二醇、环戊二醇、环己二醇、环庚二醇、环辛二醇、双环[4.3.0]-壬二醇、二环己二醇、三环[5.3.1.1]十二烷二醇、螺环[3.4]辛二醇、丁基环己二醇等脂族多元醇;二羟基萘、三羟基萘、四羟基萘、二羟基苯、苯三醇、三羟基菲、双酚A、双酚F、苯二甲醇、四溴双酚A等芳族多元醇、以及它们与环氧乙烷或环氧丙烷等环氧烷的加成反应产物;双-[4-(羟基乙氧基)苯基]硫醚、双-[4-(2-羟基丙氧基)苯基]硫醚、双-[4-(2,3-二羟基丙氧基)苯基]硫醚、双-[4-(4-羟基环己氧基)苯基]硫醚、双-[2-甲基-4-(羟基乙氧基)-6-丁基苯基]硫醚、以及在这些化合物上每1个羟基加成平均3分子以下的环氧乙烷和/或环氧丙烷的化合物;双(2-羟乙基)硫醚、1,2-双-(2-羟乙基巯基)乙烷、双(2-羟乙基)二硫醚、1,4-二噻烷-2,5-二醇、双(2,3-二羟丙基)硫醚、四(4-羟基-2-硫杂丁基)甲烷、双(4-羟基苯基)砜(商品名:双酚S)、四溴双酚S、四甲基双酚S、4,4′-硫代双(6-叔丁基-3-甲基苯酚)、1,3-双(2-羟基乙硫基乙基)-环己烷等含有硫原子的多元醇等。
<(A1-4)多胺化合物>
作为上述多胺化合物(以下有时也简称为(A1-4)成分),例如可举出六亚甲基二胺、双(4-氨基环己基)甲烷。
<(A2)阳离子聚合性单体>
本发明的阳离子聚合性单体可不受特别限制地使用公知的单体,例如是作为用于得到环氧树脂或聚硫化物树脂等树脂的作为原料的单体。具体地可举出:作为开环聚合的单体的多环氧化合物、多环硫化合物、多硫杂环丁烷化合物、以及通过多环硫化合物与多硫醇化合物反应而得到的单体,作为单体,可不受特别限制地使用公知的多环氧化合物(以下有时也简称为(A2-1)成分)、多环硫化合物(以下有时也简称为(A2-2)成分)或多硫杂环丁烷化合物(以下有时也简称为(A2-3)成分)。另外,关于多硫醇化合物,可举出上述(A1-2)中例示的那些。
以下,详细说明阳离子聚合性单体。
<(A2-1)多环氧化合物>
作为上述多环氧化合物,可大致分为脂族环氧化合物、脂环族环氧化合物和芳族环氧化合物,作为其具体例,可举出以下的化合物。
作为脂族环氧化合物,可举出:环氧乙烷、2-乙基环氧乙烷、丁基缩水甘油基醚、苯基缩水甘油基醚、2,2′-亚甲基双环氧乙烷、1,6-己二醇二缩水甘油基醚、乙二醇二缩水甘油基醚、二甘醇二缩水甘油基醚、三甘醇二缩水甘油基醚、四甘醇二缩水甘油基醚、九甘醇二缩水甘油基醚、丙二醇二缩水甘油基醚、二丙二醇二缩水甘油基醚、三丙二醇二缩水甘油基醚、四丙二醇二缩水甘油基醚、九丙二醇二缩水甘油基醚、新戊二醇二缩水甘油基醚、三羟甲基丙烷三缩水甘油基醚、甘油三缩水甘油基醚、二甘油四缩水甘油基醚、季戊四醇四缩水甘油基醚、三(2-羟乙基)异氰尿酸酯的二缩水甘油基醚、三(2-羟乙基)异氰尿酸酯的三缩水甘油基醚。
作为脂环族环氧化合物,可举出:异佛尔酮二醇二缩水甘油基醚、双-2,2-羟基环己基丙烷二缩水甘油基醚。
作为芳族环氧化合物,可举出:间苯二酚二缩水甘油基醚、双酚A二缩水甘油基醚、双酚F二缩水甘油基醚、双酚S二缩水甘油基醚、邻苯二甲酸二缩水甘油基酯、酚醛多缩水甘油基醚、甲酚醛多缩水甘油基醚。
<(A2-2)多环硫化合物>
作为上述多环硫化合物的具体例,可举出:双(1,2-环硫乙基)硫醚、双(1,2-环硫乙基)二硫醚、双(环硫乙硫基)甲烷、双(环硫乙硫基)苯、双[4-(环硫乙硫基)苯基]硫醚、双[4-(环硫乙硫基)苯基]甲烷等环硫乙硫基化合物;双(2,3-环硫丙基)硫醚、双(2,3-环硫丙基)二硫醚、双(2,3-环硫丙硫基)甲烷、1,2-双(2,3-环硫丙硫基)乙烷、1,2-双(2,3-环硫丙硫基)丙烷、1,3-双(2,3-环硫丙硫基)丙烷、1,3-双(2,3-环硫丙硫基)-2-甲基丙烷、1,4-双(2,3-环硫丙硫基)丁烷、1,4-双(2,3-环硫丙硫基)-2-甲基丁烷、1,3-双(2,3-环硫丙硫基)丁烷、1,5-双(2,3-环硫丙硫基)戊烷、1,5-双(2,3-环硫丙硫基)-2-甲基戊烷、1,5-双(2,3-环硫丙硫基)-3-硫杂戊烷、1,6-双(2,3-环硫丙硫基)己烷、1,6-双(2,3-环硫丙硫基)-2-甲基己烷、1,8-双(2,3-环硫丙硫基)-3,6-二硫杂辛烷、1,2,3-三(2,3-环硫丙硫基)丙烷、2,2-双(2,3-环硫丙硫基)-1,3-双(2,3-环硫丙硫基甲基)丙烷、2,2-双(2,3-环硫丙硫基甲基)-1-(2,3-环硫丙硫基)丁烷、1,5-双(2,3-环硫丙硫基)-2-(2,3-环硫丙硫基甲基)-3-硫杂戊烷、1,5-双(2,3-环硫丙硫基)-2,4-双(2,3-环硫丙硫基甲基)-3-硫杂戊烷、1-(2,3-环硫丙硫基)-2,2-双(2,3-环硫丙硫基甲基)-4-硫杂己烷、1,5,6-三(2,3-环硫丙硫基)-4-(2,3-环硫丙硫基甲基)-3-硫杂己烷、1,8-双(2,3-环硫丙硫基)-4-(2,3-环硫丙硫基甲基)-3,6-二硫杂辛烷、1,8-双(2,3-环硫丙硫基)-4,5-双(2,3-环硫丙硫基甲基)-3,6-二硫杂辛烷、1,8-双(2,3-环硫丙硫基)-4,4-双(2,3-环硫丙硫基甲基)-3,6-二硫杂辛烷、1,8-双(2,3-环硫丙硫基)-2,5-双(2,3-环硫丙硫基甲基)-3,6-二硫杂辛烷、1,8-双(2,3-环硫丙硫基)-2,4,5-三(2,3-环硫丙硫基甲基)-3,6-二硫杂辛烷、1,1,1-三[[2-(2,3-环硫丙硫基)乙基]硫代甲基]-2-(2,3-环硫丙硫基)乙烷、1,1,2,2-四[[2-(2,3-环硫丙硫基)乙基]硫代甲基]乙烷、1,11-双(2,3-环硫丙硫基)-4,8-双(2,3-环硫丙硫基甲基)-3,6,9-三硫杂十一烷、1,11-双(2,3-环硫丙硫基)-4,7-双(2,3-环硫丙硫基甲基)-3,6,9-三硫杂十一烷、1,11-双(2,3-环硫丙硫基)-5,7-双(2,3-环硫丙硫基甲基)-3,6,9-三硫杂十一烷等链状脂族的2,3-环硫丙硫基化合物;1,3-双(2,3-环硫丙硫基)环己烷、1,4-双(2,3-环硫丙硫基)环己烷、1,3-双(2,3-环硫丙硫基甲基)环己烷、1,4-双(2,3-环硫丙硫基甲基)环己烷、2,5-双(2,3-环硫丙硫基甲基)-1,4-二噻烷、2,5-双[[2-(2,3-环硫丙硫基)乙基]硫代甲基]-1,4-二噻烷、2,5-双(2,3-环硫丙硫基甲基)-2,5-二甲基-1,4-二噻烷等环状脂族的2,3-环硫丙硫基化合物;1,2-双(2,3-环硫丙硫基)苯、1,3-双(2,3-环硫丙硫基)苯、1,4-双(2,3-环硫丙硫基)苯、1,2-双(2,3-环硫丙硫基甲基)苯、1,3-双(2,3-环硫丙硫基甲基)苯、1,4-双(2,3-环硫丙硫基甲基)苯、双[4-(2,3-环硫丙硫基)苯基]甲烷、2,2-双[4-(2,3-环硫丙硫基)苯基]丙烷、双[4-(2,3-环硫丙硫基)苯基]硫醚、双[4-(2,3-环硫丙硫基)苯基]砜、4,4′-双(2,3-环硫丙硫基)联苯等芳族的2,3-环硫丙硫基化合物;双(2,3-环硫丙基)醚、双(2,3-环硫丙氧基)甲烷、1,2-双(2,3-环硫丙氧基)乙烷、1,2-双(2,3-环硫丙氧基)丙烷、1,3-双(2,3-环硫丙氧基)丙烷、1,3-双(2,3-环硫丙氧基)-2-甲基丙烷、1,4-双(2,3-环硫丙氧基)丁烷、1,4-双(2,3-环硫丙氧基)-2-甲基丁烷、1,3-双(2,3-环硫丙氧基)丁烷、1,5-双(2,3-环硫丙氧基)戊烷、1,5-双(2,3-环硫丙氧基)-2-甲基戊烷、1,5-双(2,3-环硫丙氧基)-3-硫杂戊烷、1,6-双(2,3-环硫丙氧基)己烷、1,6-双(2,3-环硫丙氧基)-2-甲基己烷、1,8-双(2,3-环硫丙氧基)-3,6-二硫杂辛烷、1,2,3-三(2,3-环硫丙氧基)丙烷、2,2-双(2,3-环硫丙氧基)-1,3-双(2,3-环硫丙氧基甲基)丙烷、2,2-双(2,3-环硫丙氧基甲基)-1-(2,3-环硫丙氧基)丁烷、1,5-双(2,3-环硫丙氧基)-2-(2,3-环硫丙氧基甲基)-3-硫杂戊烷、1,5-双(2,3-环硫丙氧基)-2,4-双(2,3-环硫丙氧基甲基)-3-硫杂戊烷、1-(2,3-环硫丙氧基)-2,2-双(2,3-环硫丙氧基甲基)-4-硫杂己烷、1,5,6-三(2,3-环硫丙氧基)-4-(2,3-环硫丙氧基甲基)-3-硫杂己烷、1,8-双(2,3-环硫丙氧基)-4-(2,3-环硫丙氧基甲基)-3,6-二硫杂辛烷、1,8-双(2,3-环硫丙氧基)-4,5-双(2,3-环硫丙氧基甲基)-3,6-二硫杂辛烷、1,8-双(2,3-环硫丙氧基)-4,4-双(2,3-环硫丙氧基甲基)-3,6-二硫杂辛烷、1,8-双(2,3-环硫丙氧基)-2,5-双(2,3-环硫丙氧基甲基)-3,6-二硫杂辛烷、1,8-双(2,3-环硫丙氧基)-2,4,5-三(2,3-环硫丙氧基甲基)-3,6-二硫杂辛烷、1,1,1-三[[2-(2,3-环硫丙氧基)乙基]硫代甲基]-2-(2,3-环硫丙氧基)乙烷、1,1,2,2-四[[2-(2,3-环硫丙氧基)乙基]硫代甲基]乙烷、1,11-双(2,3-环硫丙氧基)-4,8-双(2,3-环硫丙氧基甲基)-3,6,9-三硫杂十一烷、1,11-双(2,3-环硫丙氧基)-4,7-双(2,3-环硫丙氧基甲基)-3,6,9-三硫杂十一烷、1,11-双(2,3-环硫丙氧基)-5,7-双(2,3-环硫丙氧基甲基)-3,6,9-三硫杂十一烷等链状脂族的2,3-环硫丙氧基化合物;1,3-双(2,3-环硫丙氧基)环己烷、1,4-双(2,3-环硫丙氧基)环己烷、1,3-双(2,3-环硫丙氧基甲基)环己烷、1,4-双(2,3-环硫丙氧基甲基)环己烷、2,5-双(2,3-环硫丙氧基甲基)-1,4-二噻烷、2,5-双[[2-(2,3-环硫丙氧基)乙基]硫代甲基]-1,4-二噻烷、2,5-双(2,3-环硫丙氧基甲基)-2,5-二甲基-1,4-二噻烷等环状脂族的2,3-环硫丙氧基化合物;1,2-双(2,3-环硫丙氧基)苯、1,3-双(2,3-环硫丙氧基)苯、1,4-双(2,3-环硫丙氧基)苯、1,2-双(2,3-环硫丙氧基甲基)苯、1,3-双(2,3-环硫丙氧基甲基)苯、1,4-双(2,3-环硫丙氧基甲基)苯、双[4-(2,3-环硫丙氧基)苯基]甲烷、2,2-双[4-(2,3-环硫丙氧基)苯基]丙烷、双[4-(2,3-环硫丙氧基)苯基]硫醚、双[4-(2,3-环硫丙氧基)苯基]砜、4,4′-双(2,3-环硫丙氧基)联苯等芳族的2,3-环硫丙氧基化合物等。
<(A2-3)多硫杂环丁烷化合物>
作为多硫杂环丁烷化合物,可使用含有金属的硫杂环丁烷化合物或非金属的硫杂环丁烷化合物。这些多硫杂环丁烷化合物如WO2005/095490和日本特开2003-327583号公报中公开的那样在分子内含有1个以上的硫杂环丁烷基。优选为合计含有2个以上硫杂环丁烷基的化合物。例如可举出:双硫杂环丁烷基硫化物、双(3-硫杂环丁烷基硫基)二硫化物、双(3-硫杂环丁烷基硫基)甲烷、3-(((3′-硫杂环丁烷基硫基)甲硫基)甲硫基)硫杂环丁烷等硫化物系硫杂环丁烷化合物;双(3-硫杂环丁烷基)二硫化物、双(3-硫杂环丁烷基)三硫化物、双(3-硫杂环丁烷基)四硫化物、双(3-硫杂环丁烷基)五硫化物等多硫化物系硫杂环丁烷化合物等。
<(A3)自由基聚合性单体>
本发明的自由基聚合性单体可不受特别限制地使用公知的单体,例如可单独或混合使用(甲基)丙烯酸酯化合物(以下有时也简称为(A3-1)成分)、不具有(甲基)丙烯酸酯基但具有碳-碳不饱和键的自由基聚合性单体(以下有时也简称为烯属化合物或(A3-2)成分)。
<(A3-1)(甲基)丙烯酸酯化合物>
作为(甲基)丙烯酸酯化合物,可不受特别限制地使用分子中具有至少1个(甲基)丙烯酸酯基的公知化合物,若例示具体的(甲基)丙烯酸酯化合物,可举出:缩水甘油基(甲基)丙烯酸酯、三羟甲基丙烷三(甲基)丙烯酸酯、四羟甲基甲烷三(甲基)丙烯酸酯、三羟甲基丙烷三甘醇三(甲基)丙烯酸酯、季戊四醇四(甲基)丙烯酸酯、二季戊四醇六(甲基)丙烯酸酯、氨基甲酸酯低聚物四(甲基)丙烯酸酯、氨基甲酸酯低聚物六(甲基)丙烯酸酯、聚酯低聚物六(甲基)丙烯酸酯、乙二醇二(甲基)丙烯酸酯、二甘醇二(甲基)丙烯酸酯、三甘醇二(甲基)丙烯酸酯、聚乙二醇二(甲基)丙烯酸酯(特别是平均分子量为308、330、508、736)、三丙二醇二(甲基)丙烯酸酯、双酚A-二(甲基)丙烯酸酯、2,2-双[4-((甲基)丙烯酰氧基聚乙氧基)苯基]丙烷(特别是平均分子量为478、776、804)、甲氧基聚乙二醇(甲基)丙烯酸酯、甲氧基聚乙二醇(甲基)丙烯酸酯(特别是平均分子量为468)、(甲基)丙烯酸甲酯等。
<(A3-2)烯属化合物>
若例示具体的烯属化合物,可举出:甲基乙烯基酮、乙基乙烯基酮、乙基乙烯基醚、苯乙烯、乙烯基环己烷、丁二烯、1,4-戊二烯、二乙烯基硫醚、二乙烯基砜、1,2-二乙烯基苯、1,3-二乙烯基-1,1,3,3-四甲基丙烷二硅氧烷、二甘醇二乙烯基醚、己二酸二乙烯酯、癸二酸二乙烯酯、乙二醇二乙烯基醚、二乙烯基亚砜、二乙烯基过硫化物、二甲基二乙烯基硅烷、1,2,4-三乙烯基环己烷、甲基三乙烯基硅烷、α-甲基苯乙烯和α-甲基苯乙烯二聚体等。
另外,可举出:二甘醇双烯丙基碳酸酯、甲氧基聚乙二醇烯丙基醚(特别是平均分子量为550)、甲氧基聚乙二醇烯丙基醚(特别是平均分子量为350)、甲氧基聚乙二醇烯丙基醚(特别是平均分子量为1500)、聚乙二醇烯丙基醚(特别是平均分子量为450)、甲氧基聚乙二醇-聚丙二醇烯丙基醚(特别是平均分子量为750)、丁氧基聚乙二醇-聚丙二醇烯丙基醚(特别是平均分子量为1600)、甲基丙烯酰氧基聚乙二醇-聚丙二醇烯丙基醚(特别是平均分子量为560)、苯氧基聚乙二醇烯丙基醚(特别是平均分子量为600)、甲基丙烯酰氧基聚乙二醇烯丙基醚(特别是平均分子量为430)、丙烯酰氧基聚乙二醇烯丙基醚(特别是平均分子量为420)、乙烯氧基聚乙二醇烯丙基醚(特别是平均分子量为560)、苯乙烯氧基聚乙二醇烯丙基醚(特别是平均分子量为650)、甲氧基聚乙烯硫代甘醇烯丙基硫基醚(特别是平均分子量为730)等。
作为聚合性单体(A),优选为以下的组合:多异氰酸酯化合物与多硫醇化合物的组合、多异氰酸酯化合物与多元醇化合物的组合、多环硫化合物和/或多硫杂环丁烷化合物、多环硫化合物与多硫醇化合物的组合。
另外,上述中,聚合性单体(A)更优选为:多异氰酸酯化合物与多硫醇化合物的组合、或多环硫化合物与多硫醇化合物的组合。
聚合性单体(A)为多异氰酸酯化合物和多硫醇化合物的组合时,特别地,聚合性单体(A)优选含有:选自双(异氰酸酯基甲基)双环[2.2.1]庚烷、苯二甲基二异氰酸酯、二苯基甲烷二异氰酸酯、和甲苯二异氰酸酯中的至少1种多异氰酸酯化合物,以及,选自季戊四醇四(3-巯基丙酸)酯和1,2-双(2-巯基乙硫基)-3-巯基丙烷中的至少1种多硫醇化合物。
当聚合性单体(A)为环硫化合物与多硫醇化合物的组合时,聚合性单体(A)特别优选含有:双(2,3-环硫丙基)二硫醚、以及,以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和4,8-二巯基甲基-1,11-二巯基-3,6,9-三硫杂十一烷为主成分的混合物。
<(B)极大吸收波长为360nm以上且小于380nm的苯并***系紫外线吸收剂>
本发明中,为了向光学材料赋予阻挡紫外线和蓝光的能力,含有极大吸收波长为360nm以上且小于380nm的(B)苯并***系紫外线吸收剂(以下有时也简称为(B)成分)。
本发明的苯并***系紫外线吸收剂由下述式(1)表示。
本发明中,极大吸收波长是指在吸收光谱中出现的极大吸收的顶点(凸形光谱的顶点)的波长。另外,有时会观察到多个极大吸收波长,在这种情况下,只要确认至少1个极大吸收波长在本发明特定的波长范围内即可。例如,上述的极大吸收波长为360nm以上且小于380nm的苯并***系紫外线吸收剂是指:极大吸收波长中的至少一个存在于360nm以上且小于380nm的苯并***系紫外线吸收剂。
[化2]
(其中,R1表示氢原子、碳数1~8的烷基、碳数1~8的烷氧基、羟基、碳数1~4的直链或支链的单取代氨基、碳数1~4的直链或支链的二取代氨基、硝基、羧基、烷基的碳数为1~8的烷氧羰基、碳数1~8的羟基烷基、烷基的碳数各自为1~8的烷基羰氧基烷基、烷基的碳数为1~3的羧基烷基、烷基的碳数合计为2~10的烷氧羰基烷基、芳基、酰基、磺基或氰基;R2表示羟基、碳数1~8的烷氧基、碳数1~8的烷硫基、碳数1~4的直链或支链的单取代氨基、碳数1~4的直链或支链的二取代氨基;R3表示氢原子、羟基、碳数1~8的烷基或烷氧基、碳数1~4的直链或支链的单取代氨基、碳数1~4的直链或支链的二取代氨基,也可以是R2和R3交联的环状结构。)
在通式(1)中,作为R1的具体例,可举出:氢原子;甲基、乙基、丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正己基、正辛基、2-乙基己基等可取代的碳数1~8的直链或支链的烷基;甲氧基、乙氧基、丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、正己氧基、正辛氧基、2-乙基己氧基等可取代的碳数1~8的直链或支链的烷氧基;羟基;氨基、单甲氨基、二甲氨基、单乙氨基、二乙氨基、单正丙氨基、二正丙氨基、单异丙氨基、二异丙氨基等可取代的碳数1~4的直链或支链的氨基;硝基;羧基;甲氧羰基、乙氧羰基、异丙氧羰基、正丁氧羰基、异丁氧羰基、仲丁氧羰基、叔丁氧羰基、正己氧羰基、正辛氧羰基、2-乙基己氧羰基等可取代的烷基的碳数为1~8的直链或支链的烷氧羰基;羟甲基、羟乙基、羟丙基、羟丁基、羟己基、羟辛基等可取代的碳数1~8的直链或支链的羟基烷基;甲基羰氧基甲基、乙基羰氧基甲基、丙基羰氧基甲基、丁基羰氧基甲基、己基羰氧基甲基、庚基羰氧基甲基、辛基羰氧基甲基、甲基羰氧基乙基、乙基羰氧基乙基、丙基羰氧基乙基、丁基羰氧基乙基、己基羰氧基乙基、庚基羰氧基乙基、辛基羰氧基乙基等可取代的烷基的碳数各自为1~8的直链或支链的烷基羰氧基烷基等;羧甲基、羧乙基、羧丙基等羧基烷基;甲氧羰基甲基、乙氧羰基乙基、丙氧羰基乙基等烷基的碳数各自为1~8的直链或支链的烷氧羰基烷基;苯基、苄基、甲苯基、二甲苯基等芳基;甲酰基、乙酰基、丙酰基、丁酰基、苯甲酰基等酰基;磺基;氰基等。另外,作为R2的具体例,可举出:羟基;甲氧基、乙氧基、丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、正己氧基、正辛氧基、2-乙基己氧基等可取代的碳数1~8的直链或支链的烷氧基;甲硫基、乙硫基、丙硫基、异丙硫基、正丁硫基、异丁硫基、仲丁硫基、叔丁硫基、正己硫基、正辛硫基、2-乙基己硫基等可取代的碳数1~8的直链或支链的烷硫基;单甲氨基、二甲氨基、单乙氨基、二乙氨基、单正丙氨基、二正丙氨基、单异丙氨基、二异丙氨基等可取代的碳数1~4的直链或支链的氨基等。作为R3的具体例,可举出:氢原子;羟基;甲基、乙基、丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正己基、正辛基、2-乙基己基等可取代的碳数1~8的直链或支链的烷基;甲氧基、乙氧基、丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、正己氧基、正辛氧基、2-乙基己氧基等可取代的碳数1~8的直链或支链的烷氧基;单甲氨基、二甲氨基、单乙氨基、二乙氨基、单正丙氨基、二正丙氨基、单异丙氨基、二异丙氨基等可取代的碳数1~4的直链或支链的氨基等。另外,在为R2和R3交联的环结构时,可举出亚甲基二氧基、亚乙基二氧基等。
在上述通式(1)表示的苯并***衍生物化合物中,特别优选的是:作为R1,为氢原子、甲基、甲氧基、正辛氧基、羟基、羧基、甲氧羰基、乙氧羰基、异丙氧羰基、正丁氧羰基、异丁氧羰基、仲丁氧羰基、叔丁氧羰基、正己氧羰基、正辛氧羰基、羟乙基、甲基羰氧基乙基、庚基羰氧基乙基,作为R2,为甲氧基、乙氧基、正辛氧基、二甲氨基、二乙氨基,作为R3,为氢原子、甲基、乙基、甲氧基、乙氧基、正辛氧基、二甲氨基,当为R2和R3交联的环结构时,为亚甲基二氧基。
在此,从极大吸收波长的观点考虑,优选R2或R2和R3选择供电子性取代基,和/或R1选择吸电子性取代基。
作为供电子性取代基,可举出:羟基、碳数1~8的烷氧基、碳数1~8的烷硫基、碳数1~4的直链或支链的单取代氨基、碳数1~4的直链或支链的二取代氨基。如上所述,当R2与R3交联且形成亚甲基二氧基时,R2和R3为供电子性取代基。另外,作为吸电子性取代基,可举出:硝基、羧基、烷氧羰基、酰基、磺基、氰基。
作为本发明的通式(1)表示的苯并***衍生物化合物,例如可举出:2-(2-羟基-4-二甲氨基苯基)-5-甲氧羰基-2H-苯并***、2-(2-羟基-4-二甲氨基苯基)-5-乙氧羰基-2H-苯并***、2-(2-羟基-4-二甲氨基苯基)-5-丁氧羰基-2H-苯并***、2-(2-羟基-4-二甲氨基苯基)-5-辛氧羰基-2H-苯并***、2-(2-羟基-4-二甲氨基苯基)-5-甲基-2H-苯并***、2-(2-羟基-4-二乙氨基苯基)-5-丁氧羰基-2H-苯并***、2-(2-羟基-4-二甲氨基-5-甲基苯基)-5-甲氧羰基-2H-苯并***、2-(2-羟基-4-二甲氨基-5-甲基苯基)-5-丁氧羰基-2H-苯并***、2-(2-羟基-4-二甲氨基-5-甲基苯基)-5-辛氧羰基-2H-苯并***、2-(2-羟基-4-二甲氨基-5-甲基苯基)-5-甲基-2H-苯并***、2-(2-羟基-4,5-二甲氧基苯基)-5-甲氧羰基-2H-苯并***、2-(2-羟基-4,5-二甲氧基苯基)-5-丁氧羰基-2H-苯并***、2-(2-羟基-4,5-二甲氧基苯基)-5-辛氧羰基-2H-苯并***、2-(2-羟基-4,5-二甲氧基苯基)-5-甲基-2H-苯并***、6-(5-庚基羰氧基乙基-2H-苯并***-2-基)苯并[1,3]间二氧杂环戊烯-5-醇、6-(5-异庚基羰氧基乙基-2H-苯并***-2-基)苯并[1,3]间二氧杂环戊烯-5-醇、6-(5-辛氧基-2H-苯并***-2-基)苯并[1,3]间二氧杂环戊烯-5-醇、6-(5-甲基羰氧基乙基-2H-苯并***-2-基)苯并[1,3]间二氧杂环戊烯-5-醇、7-(5-甲氧羰基-2H-苯并***-2-基)苯并[1,4]二英-6-醇、7-(5-丁氧羰基-2H-苯并***-2-基)苯并[1,4]二英-6-醇、7-(5-辛氧羰基-2H-苯并***-2-基)苯并[1,4]二英-6-醇、7-(5-甲基-2H-苯并***-2-基)苯并[1,4]二英-6-醇等。
上述式(1)中,(B)成分优选为R2与R3交联且形成了亚甲基二氧基的化合物。具体地,作为(B)成分,优选为6-(5-庚基羰氧基乙基-2H-苯并***-2-基)苯并[1,3]间二氧杂环戊烯-5-醇、6-(5-异庚基羰氧基乙基-2H-苯并***-2-基)苯并[1,3]间二氧杂环戊烯-5-醇、6-(5-辛氧基-2H-苯并***-2-基)苯并[1,3]间二氧杂环戊烯-5-醇、6-(5-甲基羰氧基乙基-2H-苯并***-2-基)苯并[1,3]间二氧杂环戊烯-5-醇等,其中更优选为6-(5-庚基羰氧基乙基-2H-苯并***-2-基)苯并[1,3]间二氧杂环戊烯-5-醇。
为了使操作性良好且有效地发挥效果,上述(B)成分的吸光系数优选为10~200(L/(g·cm))的范围。通过满足该范围,能够在不降低聚合固化光学材料用组合物而得到的光学材料的强度的情况下得到对紫外线和蓝光的阻挡性能优异的效果。
另外,通过使上述(B)成分的配合量相对于上述(A)成分100质量份,为0.005~0.3质量份,具有阻挡紫外线和蓝光的能力优异的效果,而且能够在不降低得到的光学材料的强度的情况下进行聚合固化。为了进一步提高该效果,上述(B)化合物的配合量更优选为0.01~0.2质量份。
含有上述(A)成分和(B)成分的本发明的光学材料用组合物的紫外线吸收剂不易析出,长期保存稳定性优异。
<添加剂>
为了聚合固化,在本发明的光学材料用组合物中可以根据需要添加聚合催化剂或聚合引发剂。另外,在不损害效果的范围内,作为其他任意成分,本发明的光学材料用组合物可以含有公知的各种配合剂,例如,抗静电剂、内部离型剂、抗氧化剂、抗着色剂、荧光染料、染料、颜料、香料、溶剂、流平剂、树脂改性剂、光稳定剂、红外线吸收剂、可见光吸收剂等。进而,除了上述紫外线吸收剂以外,也可以含有极大吸收波长在360nm以上且小于380nm的范围以外的公知的紫外线吸收剂。
·聚合催化剂
若例示具体的反应催化剂,可举出以下物质。
叔胺;三乙胺、三丙胺、二丙基乙胺、三丁胺、二甲基环己胺、三亚乙基二胺、四甲基亚乙基二胺、N,N-二环己基甲胺、N,N-二异丙基乙胺、N-异丙基-N-甲基丁胺、N-甲基哌啶、N-乙基哌啶、N,N-二甲基哌嗪、N,N-二乙基哌嗪、六亚甲基四胺、N-甲基吗啉、N-乙基吗啉、N-甲基哌啶酮、N-甲基吡咯烷、N-乙基吡咯烷、N-甲基吡咯烷酮、N,N-二甲基苄胺、N,N-二甲基苯胺、N-甲基二苄胺、吡啶、N-甲基吡唑、1-甲基咪唑、1,2-二甲基咪唑、苄基甲基咪唑、N-甲基吡咯、二苯基甲胺。
膦类:三甲基膦、三乙基膦、三正丙基膦、三异丙基膦、三正丁基膦、三苯基膦、三苄基膦、1,2-双(二苯基膦)乙烷、1,2-双(二甲基膦)乙烷。
季铵盐类:四甲基溴化铵、四丁基氯化铵、四丁基溴化铵、三乙基苄基氯化铵、十六烷基二甲基苄基氯化铵、1-正十二烷基氯化吡啶。
路易斯酸:三苯基铝、二甲基二氯化锡、双(巯基乙酸异辛酯)二甲基锡、二丁基二氯化锡、二月桂酸二丁基锡、马来酸二丁基锡、马来酸二丁基锡聚合物、二蓖麻油酸二丁基锡、双(十二烷硫醇)二丁基锡、双(巯基乙酸异辛酯)二丁基锡、二辛基二氯化锡、马来酸二辛基锡、马来酸二辛基锡聚合物、双(马来酸丁酯)二辛基锡、二月桂酸二辛基锡、二蓖麻油酸二辛基锡、二油酸二辛基锡、二(6-羟基)己酸二辛基锡、双(巯基乙酸异辛酯)二辛基锡、二蓖麻油酸二(十二烷基)锡;其他各种金属盐,例如,油酸铜、乙酰丙酮酸铜、乙酰丙酮酸铁、环烷酸铁、乳酸铁、柠檬酸铁、葡糖酸铁、辛酸钾、钛酸2-乙基己酯。
有机磺酸:甲磺酸、苯磺酸、对甲苯磺酸。
以(A)成分的合计量为100质量份,聚合催化剂的添加量适宜为0.001~1质量份,优选为0.002~0.5质量份,更优选为0.005~0.4质量份。
·聚合引发剂
作为聚合引发剂,可不受特别限制地使用公知的热聚合引发剂、光聚合引发剂等。若例示代表性的聚合引发剂,可举出以下的聚合引发剂。
热聚合引发剂:过氧化苯甲酰、过氧化对氯苯甲酰、过氧化癸酰、过氧化月桂酰、过氧化乙酰等过氧化二酰;过氧化2-乙基己酸叔丁酯、过氧化新癸酸叔丁酯、过氧化新癸酸异丙苯酯、过氧化苯甲酸叔丁酯等过氧酯;过氧化二碳酸二异丙酯、过氧化二碳酸二仲丁酯等过氧化碳酸酯;偶氮双异丁腈等偶氮化合物等。
光聚合引发剂:二苯甲酮;2,2-二甲氧基-1,2-二苯基乙烷-1-酮、1-羟基环己基苯基酮、2-羟基-2-甲基-1-苯基丙烷-1-酮、1-[4-(2-羟基乙氧基)-苯基]-2-羟基-2-甲基-1-丙烷-1-酮、2-甲基-1-[4-(甲硫基)苯基]-2-吗啉代丙烷-1-酮、2-苄基-2-二甲氨基-1-(4-吗啉代苯基)-丁酮-1,1-(4-异丙基苯基)-2-羟基-2-甲基丙烷-1-酮等苯乙酮系化合物;1,2-二苯基乙烷二酮、甲基苯基乙醛酸酯等α-二羰基系化合物;2,6-二甲基苯甲酰基二苯基氧化膦、双(2,4,6-三甲基苯甲酰基)-苯基氧化膦、双(2,6-二甲氧基苯甲酰基)-2,4,4-三甲基-戊基氧化膦、2,4,6-三甲基苯甲酰基二苯基氧化膦、2,4,6-三甲基苯甲酰基二苯基膦酸甲酯、2,6-二氯苯甲酰基二苯基氧化膦、2,6-二甲氧基苯甲酰基二苯基氧化膦等酰基氧化膦系化合物;1,2-辛烷二酮-1-[4-(苯硫基)-2-(O-苯甲酰肟)]等。
聚合引发剂的添加量以(A)成分的合计量为100质量份,优选为0.01~0.5质量份,更优选为0.05~0.4质量份。
·内部离型剂
作为内部离型剂,可举出:氟系非离子表面活性剂、硅系非离子表面活性剂、烷基季铵盐、磷酸酯、酸性磷酸酯、氧基亚烷基型酸性磷酸酯、酸性磷酸酯的碱金属盐、氧基亚烷基型酸性磷酸酯的碱金属盐、高级脂肪酸的金属盐、高级脂肪酸酯、石蜡、蜡、高级脂族酰胺、高级脂族醇、聚硅氧烷类、脂族胺环氧乙烷加成物等。例如,作为酸性磷酸酯,可使用:STEPAN公司制的ZelecUN、三井化学株式会社制的MR用内部离型剂、城北化学工业株式会社制的JP系列、东邦化学工业株式会社制的Phosphanol系列、大八化学工业株式会社制的AP、DP系列等。
·树脂改性剂
为了调节树脂的光学物性、耐冲击性、比重等各种物性以及调节光学材料用组合物的粘度和适用期,可以在不损害本实施方式的效果的范围内,在本发明的光学材料用组合物中添加树脂改性剂。例如可使用:环硫化物化合物、醇化合物、胺化合物、环氧化合物、有机酸及其酸酐、含有(甲基)丙烯酸酯化合物的烯烃化合物等。
·可见光吸收剂
作为可见光吸收剂,只要是极大吸收波长为400nm~750nm的范围的化合物,就可以没有特别制限地使用。例如可使用:苝系化合物、卟啉化合物、类胡萝卜素系化合物、菁系化合物、酞菁系化合物、蒽醌系化合物、靛蓝系化合物、钕化合物、四氮杂卟啉化合物等。
<光学材料>
本发明的光学材料含有将上述光学材料用组合物聚合固化而成的固化物。该光学材料优选:波长400nm的光线透射率为5%以下且波长420nm的光线透射率为70%以下,且对380~500nm的波长区域的光线阻挡率(也称为蓝光阻挡率)为35%以上。
光学材料的波长400nm的光线透射率更优选为3%以下,进一步优选为1%以下。
光学材料的波长420nm的光线透射率更优选为65%以下,进一步优选为60%以下。
380~500nm的波长区域的光线阻挡率更优选为38%以上、进一步优选为40%以上。
予以说明,关于380~500nm的波长区域的光线阻挡率,在380nm至500nm的波长区域,每隔10nm求透射率,由这些每隔10nm的透射率的平均值(也称为380~500nm的透射率(T)的平均值)来计算,通过下式求出。
蓝光阻挡率=100-(380~500nm的透射率(T)的平均值)
聚合固化本发明的光学材料用组合物而得到的光学材料的使用用途没有特别限制,可适用于通常的眼镜透镜、护目镜、视力矫正用眼镜透镜、摄像设备用透镜、液晶投影仪用菲涅耳透镜、双凸透镜、接触透镜等各种塑料透镜。
作为光学材料的制造方法,可举出如下方法:将选自上述式(1)中的1种以上的苯并***系紫外线吸收剂与聚合性单体混合而成为光学材料用组合物,然后使用公知的制造方法进行聚合固化和成型。
使用光学材料用组合物的上述塑料透镜的制造方法没有特殊限定,通常可采用浇铸聚合。例如,在光学材料用组合物中根据需要混合聚合引发剂,向透镜成型用铸模中注入该混合液,通常在-20℃~150℃之间加热,由此得到塑料透镜。
<光学材料的二次加工:涂层的层叠>
聚合固化本发明的光学材料用组合物而得到的光学材料、特别是含有上述光学材料的塑料透镜可以根据需要在单面或两面上施加涂层来使用。
作为涂层,具体地可举出:底漆层、硬涂层、防反射层、防雾涂层、防污层、疏水层等。这些涂层既可以分别单独使用,也可以将多个涂层形成多层来使用。当在两面上施加涂层时,在各面上既可以施加相同的涂层,也可以施加不同的涂层。
这些涂层分别可以并用公知的紫外线吸收剂、用于保护眼睛免受红外线伤害的红外线吸收剂、用于提高透镜耐候性的光稳定剂或抗氧化剂、用于提高透镜的时尚性的染料或颜料、以及光致变色染料或光致变色颜料、抗静电剂,除此以外,还可以并用用于提高透镜性能的公知的添加剂。关于通过涂布施加涂料的层,可以使用用于改善涂布性的各种流平剂。
在设置硬涂层时,通过涂布含有有机硅化合物、氧化锡、氧化硅、氧化锆、氧化钛等微粒状无机物等的涂布液并使之固化而得到。另外,为了提高耐冲击性或提高与硬涂层之间的密合性,可以在塑料透镜的表面上设置以聚氨酯为主成分的底漆层。进而,为了赋予防反射性能,也可以在硬涂层上使用氧化硅、二氧化钛、氧化锆、氧化钽等来施加防反射层。进而,为了提高疏水性,可以在该防反射层上使用具有氟原子的有机硅化合物来施加疏水膜。
实施例
以下,举出实施例以具体说明本发明,但本发明不限定于这些实施例。
聚合固化光学材料用组合物而得到的塑料透镜的物性通过如下方法求出。
(1)400nm、420nm的光线透射率的测定
使用分光光度计(UV-2550,岛津制作所株式会社制)测定波长380~800nm的透射率,求出上述波长的光线透射率和视觉透射率。
(2)蓝色区域(380nm~500nm的波长区域)的光线阻挡率的测定
使用分光光度计(UV-2550,岛津制作所株式会社制)测定波长380~500nm的透射率,由每隔10nm的透射率(T(%)),通过下式计算蓝光阻挡率。
蓝光阻挡率(%)=100-(380~500nm的透射率(T)的平均值)
紫外线吸收剂的极大吸收波长通过如下方法求出。
作为测定仪器,使用株式会社岛津制作所制的岛津分光光度计UV-2550。测定通过如下方式进行:制备将测定对象物溶解在溶剂(氯仿)中的溶液(浓度1.0×10-4mol/L),使用光路长10mm的石英池来测定。
实施例1
向双(异氰酸酯基甲基)双环[2.2.1]庚烷50.28质量份中添加作为催化剂的二甲基二氯化锡0.06质量份、作为离型剂的酸性磷酸酯JP-506H(城北化学工业株式会社制)0.15质量份、作为紫外线吸收剂的6-(5-庚基羰氧基乙基-2H-苯并***-2-基)苯并[1,3]间二氧杂环戊烯-5-醇(极大吸收波长:367nm)0.04质量份,搅拌混合后,进一步添加季戊四醇四(3-巯基丙酸)酯25.50质量份、1,2-双(2-巯基乙硫基)-3-巯基丙烷24.22质量份,在10mmHg的减压下搅拌混合30分钟,制备光学材料用组合物。接着,将该光学材料用组合物注入预先准备的包括玻璃制模具和树脂垫的透镜成型用铸模(中心厚度2.0mm)中,在电炉中在20℃~120℃放置24小时进行聚合。聚合结束后,取出垫和模具,然后在120℃热处理2小时,得到塑料透镜。得到的透镜的评价结果示于表1。
实施例2
向苯二甲基二异氰酸酯52.02质量份中添加作为催化剂的二甲基二氯化锡0.04质量份、作为离型剂的酸性磷酸酯JP-506H(城北化学工业株式会社制)0.15质量份、作为紫外线吸收剂的6-(5-庚基羰氧基乙基-2H-苯并***-2-基)苯并[1,3]间二氧杂环戊烯-5-醇(极大吸收波长:367nm)0.04质量份,搅拌混合后,进一步添加1,2-双(2-巯基乙硫基)-3-巯基丙烷47.98质量份,在10mmHg的减压下搅拌混合30分钟,制备光学材料用组合物。将该光学材料用组合物注入预先准备的包括玻璃制模具和树脂垫的透镜成型用铸模(中心厚度2.0mm)中,在电炉中在20℃~120℃放置24小时进行聚合。聚合结束后,取出垫和模具,然后在120℃热处理2小时,得到塑料透镜。得到的透镜的评价结果示于表1。
实施例3
向充分干燥的烧瓶中装入6-(5-庚基羰氧基乙基-2H-苯并***-2-基)苯并[1,3]间二氧杂环戊烯-5-醇(极大吸收波长:367nm)0.04质量份、双(2,3-环硫丙基)二硫醚90.9质量份,在20℃下搅拌1小时,制备溶液。向该溶液中加入将N,N-二甲基环己胺0.019质量份、N,N-二环己基甲胺0.09质量份溶解在以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和4,8-二巯基甲基-1,11-二巯基-3,6,9-三硫杂十一烷为主成分的混合物9.1质量份中而得到的溶液,在20℃下搅拌30分钟,制备光学材料用组合物。将该光学材料用组合物在600Pa下脱泡1小时,通过1μmPTFE过滤器进行过滤后,将该光学材料用组合物注入预先准备的包括玻璃制模具和树脂垫的透镜成型用铸模(中心厚度2.0mm)中。将该玻璃模具在30℃~80℃放置21小时进行聚合。聚合结束后,取出垫和模具,然后在120℃热处理3小时,得到塑料透镜。得到的透镜的评价结果示于表1。
实施例4
将甲基丙烯酸甲酯90.00质量份、乙二醇二甲基丙烯酸酯10.00质量份、作为紫外线吸收剂的6-(5-庚基羰氧基乙基-2H-苯并***-2-基)苯并[1,3]间二氧杂环戊烯-5-醇(极大吸收波长:367nm)0.04质量份、和作为热聚合引发剂的偶氮双异丁腈0.10质量份混合,在室温下充分搅拌后,减压至50mmHg,脱气10分钟,得到光学材料用组合物。接着,将该光学材料用组合物注入预先准备的包括玻璃制模具和树脂垫的透镜成型用铸模(中心厚度2.0mm)中,在电炉中在40℃~85℃放置24小时进行聚合。聚合结束后,取出垫和模具,然后在100℃热处理2小时,得到塑料透镜。得到的透镜的评价结果示于表1。
实施例5~8
在实施例1~4中,将紫外线吸收剂的添加量变更为如表1所示,除此以外,与实施例1~4同样操作,得到塑料透镜。得到的透镜的评价结果示于表1。
上述实施例1~8制作的光学材料用组合物确认在室温(25℃)下在24小时以内没有紫外线吸收剂的析出,长期保存稳定性优异。
比较例1、2
在实施例1、5中,将紫外线吸收剂变更为2-(3-叔丁基-2-羟基-5-甲基苯基)-5-氯-2H-苯并***(极大吸收波长:352nm),除此以外,以同样方式得到塑料透镜。得到的透镜的评价结果示于表1。
[表1]
表中示出的聚合性单体(A)、紫外线吸收剂(B)如下所示。
(聚合性单体)
A1:双(异氰酸酯基甲基)双环[2.2.1]庚烷
A2:季戊四醇四(3-巯基丙酸)酯
A3:1,2-双(2-巯基乙硫基)-3-巯基丙烷
A4:苯二甲基二异氰酸酯
A5:双(2,3-环硫丙基)二硫醚
A6:以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、和4,8-二巯基甲基-1,11-二巯基-3,6,9-三硫杂十一烷为主成分的混合物
A7:甲基丙烯酸甲酯
A8:乙二醇二甲基丙烯酸酯
(紫外线吸收剂)
B1:6-(5-庚基羰氧基乙基-2H-苯并***-2-基)苯并[1,3]间二氧杂环戊烯-5-醇
B2:2-(3-叔丁基-2-羟基-5-甲基苯基)-5-氯-2H-苯并***
由以上的实施例、比较例的结果,可知以下结论。
实施例1~8均能够阻挡对眼睛有害的紫外线和蓝光,有效地抑制蓝光危害。与此相比,比较例1、2的波长420nm的光线透射率高、且蓝光阻挡率低,由此可知,当使用本发明范围以外的紫外线吸收剂时,蓝光阻挡性能不充分。
Claims (5)
2.权利要求1所述的光学材料用组合物,其中,上述聚合性单体(A)含有:
选自双(异氰酸酯基甲基)双环[2.2.1]庚烷、苯二甲基二异氰酸酯、二苯基甲烷二异氰酸酯、和甲苯二异氰酸酯中的至少1种多异氰酸酯化合物,以及
选自季戊四醇四(3-巯基丙酸)酯和1,2-双(2-巯基乙硫基)-3-巯基丙烷中的至少1种多硫醇化合物。
3.权利要求1所述的光学材料用组合物,其中,上述聚合性单体(A)含有:
双(2,3-环硫丙基)二硫醚,以及
以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和4,8-二巯基甲基-1,11-二巯基-3,6,9-三硫杂十一烷为主成分的混合物。
4.光学材料,其是含有由将权利要求1~3任一项所述的光学材料用组合物聚合固化而成的固化物的光学材料,其中,波长400nm的光线透射率为5%以下,且波长420nm的光线透射率为70%以下,且380~500nm的波长区域的光线阻挡率为35%以上。
5.塑料透镜,其含有权利要求4所述的光学材料。
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