CN104024300B - 含硫代环氧基(thioepoxy)化合物的光学材料聚合合成物与光学材料制造方法 - Google Patents
含硫代环氧基(thioepoxy)化合物的光学材料聚合合成物与光学材料制造方法 Download PDFInfo
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- CN104024300B CN104024300B CN201280063547.5A CN201280063547A CN104024300B CN 104024300 B CN104024300 B CN 104024300B CN 201280063547 A CN201280063547 A CN 201280063547A CN 104024300 B CN104024300 B CN 104024300B
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Abstract
本发明涉及一种可避免未硬化或聚合不均匀现象,获得高品质硫代环氧基系光学材料的光学材料用聚合合成物与光学材料的制造方法。发明提供一种硫代环氧基系光学材料制造方法,包括含pH4~8的硫代环氧基化合物的聚合性合成物制造阶段,把所述聚合性合成物注模聚合的阶段。本发明制造的硫代环氧基系光学材料可以代替现有光学材料,广泛应用于多种领域。
Description
技术领域
本发明涉及聚合硫代环氧基化合物的光学材料制造方法,尤其涉及一种可避免未硬化或聚合不均匀现象,获得高品质硫代环氧基系光学材料的光学材料用聚合合成物与光学材料的制造方法。
背景技术
韩国注册专利10-0681218号公开了一种硫代环氧基系塑料镜片。硫代环氧基系镜片屈光率高,并具有高阿贝数,性能优秀,但问题在于镜片容易破碎,不易染色。为了解决这一问题,韩国注册专利10-0417985号,日本公开专利平11-352302等公开了聚合两种不同性质的树脂的方法,即聚合硫代环氧基化合物与聚硫醇化合物及聚异氰酸酯化合物的方法。
硫代环氧基系镜片或共聚硫代环氧基与硫乌拉坦而来的硫代环氧基系镜片,在把聚合性合成物注模聚合时,都很难硬化,导致聚合不均匀问题,引发脉理或白浊、气泡等,经常出现镜片品质低下的问题。这种未硬化和由此引发的聚合不均匀会导致镜片的收率降低,成为增加生产成本的要因。目前,镜片领域的主要关切点之一是降低生产成本,含硫代环氧基化合物的光学材料存在的未硬化及聚合不均匀问题急需改善。
发明内容
发明的课题
本发明的各发明人在通过包括硫代环氧基化合物的聚合性合成物聚合形成镜片的过程中,偶然发现硫代环氧基化合物的pH不同时,硬化程度有很大差别。硫代环氧基化合物的pH比本发明的发明人确认的适当范围低或高的状态下,合成物的硬化不顺利,很难正常获得镜片,或者即便发生硬化,也因聚合不均匀,导致质量下降,很难使用镜片,或者收率大幅下降。但硫代环氧基化合物的pH处于本发明确认的适当范围内时,由于合成物的硬化非常好,可以避免聚合不均匀,可以容易制造高质量光学镜片。
本发明是验证这一点后完成的发明,其目的在于提供一种利用包括含一个以上硫代环氧基的化合物的光学材料用聚合性合成物,避免未硬化或聚合不均匀,以高收率制造高品质硫代环氧基系光学材料的制造方法及用于此的硫代环氧基系光学材料用聚合性合成物。
实施方案
本发明中“硫代环氧基化合物”的定义为具有1个以上硫代环氧基的化合物。
本发明中“硫代环氧基系光学材料”如没有特别限制,则包括聚合硫代环氧基化合物而得的光学材料和共聚硫代环氧基和硫乌拉坦而得的光学材料。
本发明提供一种硫代环氧基系光学材料制造方法,包括含pH4~8的硫代环氧基化合物的聚合性合成物制造阶段,
把所述聚合性合成物注模聚合的阶段。
本发明提供一种
含pH4~8的硫代环氧基化合物的光学材料用聚合性合成物。
另外,本发明提供一种硬化所述聚合性合成物而得的光学材料和由该光学材料形成的光学镜片。所述光学镜片尤其包括眼镜镜片或偏光镜片。
发明效果
本发明把硫代环氧基化合物的pH值控制在特定范围内,可以防止由未硬化或聚合不均匀引发的脉理、白化、气泡,可制造无色透明、无变形的高品质镜片,可以提高收率、降低生产成本。
具体实施方式
本发明提供一种硫代环氧基系光学材料制造方法,包括含pH4~8的硫代环氧基化合物的聚合性合成物制造阶段,把该聚合性合成物注模聚合的阶段。
如硫代环氧基化合物的pH低于4或高于8,则聚合时硬化不顺畅,很难正常获得镜片,即便一部分发生硬化,也因聚合不均匀,引发品质下降,很难使用所得镜片。聚合不均匀引发的问题通常有脉理、白化、边缘发生气泡等,如果超出所述范围,则即便产生一定程度的硬化,也会因脉理、白化或气泡的发生,导致镜片的品质下降,降低收率,增加生产升本。相反,以硫代环氧基化合物的pH为4~8的条件制造聚合性合成物,进行聚合反应时,即便不改变其他条件,也能克服硫代环氧基系光学材料的制造过程中出现的硬化困难问题,可以容易制造光学材料。
所述硫代环氧基化合物比如可以是1种以上选自1,3-及1,4-二(β-环硫代丙基硫代)环己烷)(bis(β-epithiopropylthio)cyclo hexane)、1,3-及1,4-二(β-环硫代丙基硫代甲基)环己烷)(bis(β-epithiopropylthiomethyl)cyclo hexane)、二[4-(β-环硫代丙基硫代)环己基]甲烷(bis[4-(β-epithiopropylthio)cyclo hexyl]methane)、2,2-二[4-(β-环硫代丙基硫代)环己基]丙烷(2,2-bis[4-(β-epithiopropylthio)cyclo hexyl]propane)、二[4-(β-环硫代丙基硫代)环己基]硫化物(bis[4-(β-epithiopropylthio)cyclo hexyl]sulfide)等具有脂环族骨骼的环硫化物化合物;1,3-及1,4-二(β-环硫代丙基硫代甲基)苯bis(β-epithiopropylthiomethyl)benzene)、二[4-(β-环硫代丙基硫代)苯基]甲烷(bis[4-(β-epithiopropylthio)phenyl]methane)、2,2-二[4-(β-环硫代丙基硫代)苯基]丙烷(2,2-bis[4-(β-epithiopropylthio)phenyl]propane)、二[4-(β-环硫代丙基硫代)苯基]硫化物(bis[4-(β-epithiopropylthio)phenyl]sulfide)、二[4-(β-环硫代丙基硫代)苯基]二硫化物(bis[4-(β-epithiopropylthio)phenyl]disulfide)、二[4-(β-环硫代丙基硫代)苯基]硫(bis[4-(β-epithiopropylthio)phenyl]sulfin)、4,4-二(β-环硫代丙基硫代)二苯基(4,4-bis(β-epithiopropylthio)biphenyl)等具有芳香族骨骼的环硫化物化合物;2,5-二(β-环硫代丙基硫代甲基)-1,4-二噻烷(2,5-bis(β-epithiopropylthiomethyl)-1,4-dithiane)、2,5-二(β-环硫代丙基硫代乙基硫代甲基)-1,4-二噻烷(2,5-bis(β-epithiopropylthioethylthiomethyl)-1,4-dithiane)、2,5-二(β-环硫代丙基硫代乙烷基)-1,4-二噻烷(2,5-bis(β-epithiopropylthioethyl)-1,4-dithiane)、2,3,5-三(β-环硫代丙基硫代乙烷基)-1,4-二噻烷(2,3,5-tri(β-epithiopropylthioethyl)-1,4-dithiane)等具有二噻烷(dithiane)链骨骼的环硫化物化合物;2-(2-β-环硫代丙基硫代乙基硫代)-1,3-二(β-环硫代丙基硫代)丙烷(2-(2-β-epithiopropylthioethylthio)-1,3-bis(β-epithiopropylthio)propane)、1,2-二[(2-β-环硫代丙基硫代乙烷基)硫代]-3-(β-环硫代丙基硫代)丙烷(1,2-bis[(2-β-epithiopropylthioethyl)thio]-3-(β-epithiopropylthio)propane)、四(β-环硫代丙基硫代甲基)甲烷)(Tetrakis(β-epithiopropylthiomethyl)methane)、1,1,1-三(β-环硫代丙基硫代甲基)丙烷(1,1,1-tris(β-epithiopropylthiomethyl)propane)、二-(β-环硫代丙基)硫化物(bis-(β-epithiopropyl)sulfide)、二-(β-环硫代丙基)二硫化物(bis-(β-epithiopropyl)disulfide)等具有脂肪族骨骼的环硫化物(episulfide)化合物。除此之外,还可以使用带环硫化(episulfide)基的化合物的氯取代产物(substitutionproduct)、溴取代产物等卤族取代产物、烷基取代产物(alkyl substitution product)、烷氧基取代产物(alkoxy substitution product)、硝基取代产物(nitro substitutionproduct)或与聚硫醇的预聚物(prepolymer)型变性产物(denaturant)。作为硫代环氧基化合物最好是使用二-(2,3-环硫代丙基)硫化物(bis-(2,3-epithiopropyl)sulfide)、二-(2,3-环硫代丙基)二硫化物(bis-(2,3-epithiopropyl)disulfide)、1,3-及1,4-二(β-环硫代丙基硫代)环己烷)、1,3-及1,4-二(β-环硫代丙基硫代甲基)环己烷)、2,5-二(β-环硫代丙基硫代甲基)-1,4-二噻烷、2,5-二(β-环硫代丙基硫代乙基硫代甲基)-1,4-二噻烷、2-(2-β-环硫代丙基硫代乙基硫代)-1,3-二(β-环硫代丙基硫代)丙烷中的1种以上。
所述聚合性合成物还可以包括聚硫醇化合物。所述聚硫醇化合物没有特别限制,只要是具有1个以上硫醇基的化合物,即可单独使用或混合2种以上使用。比如,可以使用二(2-巯基乙基)硫化物(bis(2-mercapto ethyl)sulfide)、4-巯基甲基-1,8-二巯基-3,6-二硫代辛烷(4-mercapto methyl-1,8-dimercapto-3,6-dithia octane)、2,3-二(2-巯基乙基硫代)丙烷-1-硫醇(2,3-bis(2-mercapto ethyl thio)propane-1-thiol)、1,3-及1,4-苯二甲醇硫醇(benzene di methanol thiol)(1,3-及1,4-亚二甲苯基二硫醇(xylylenedithiol))、2,2-二(巯基甲基)-1,3-丙烷二硫醇(2,2-bis(mercapto methyl)-1,3-propane dithiol)、四(巯基甲基)甲烷(Tetrakis(mercapto methyl)methane);2-(2-巯基乙基硫代)丙烷-1,3-二硫醇(2-(2-mercapto ethyl thio)propane-1,3-dithiol)、2-(2,3-二(2-巯基乙基硫代)丙基硫代)乙烷硫醇(2-(2,3-bis(2-mercapto ethyl thio)propylthio)ethane thiol)、二(2,3-二巯基丙醇)硫化物(bis(2,3-dimercapto propanol)sulfide)、二(2,3-二巯基丙醇)二硫化物(bis(2,3-dimercapto propanol)disulfide)、1,2-二(2-巯基乙基硫代)-3-巯基丙烷(1,2-bis(2-mercapto ethyl thio)-3-mercaptopropane)、1,2-二(2-(2-巯基乙基硫代)-3-巯基丙基硫代)乙烷(1,2-bis(2-(2-mercaptoethyl thio)-3-mercapto propyl thio)ethane)、二(2-(2-巯基乙基硫代)-3-巯基丙基)硫化物(bis(2-(2-mercapto ethyl thio)-3-mercapto propyl)sulfide)、2-(2-巯基乙基硫代)-3-2-巯基-3-[3-巯基-2-(2-巯基乙基硫代)-丙基硫代]丙基硫代-丙烷-1-硫醇(2-(2-mercapto ethyl thio)-3-2-mercapto-3-[3-mercapto-2-(2-mercapto ethyl thio)-propyl thio]propyl thio-propane-1-thiol)、2,2-二-(3-巯基-丙酰氧甲基)-丁酯(2,2-bis-(3-mercapto-propionyl oxymethyl)-butyl ester)、2-(2-巯基乙基硫代)-3-(2-(2-[3-巯基-2-(2-巯基乙基硫代)-丙基硫代]乙基硫代)乙基硫代)丙烷-1-硫醇(2-(2-mercapto ethyl thio)-3-(2-(2-[3-mercapto-2-(2-mercapto ethyl thio)-propylthio]ethyl thio)ethyl thio)propane-1-thiol)、(4R,11S)-4,11-二(巯基甲基)-3,6,9,12-四硫代四癸烷-1,14-二硫醇((4R,11S)-4,11-bis(mercapto methyl)-3,6,9,12-Tetrathia Tetra decane-1,14-dithiol)、(S)-3-((R-2,3-二巯基丙基)硫代)丙烷-1,2-二硫醇((S)-3-((R-2,3-dimercapto propyl)thio)propane-1,2-dithiol)、(4R,14R)-4,14-二(巯基甲基)-3,6,9,12,15-五硫代庚烷-1,17-二硫醇((4R,14R)-4,14-bis(mercaptomethyl)-3,6,9,12,15-Penta thia heptane-1,17-dithiol)、(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((S)-3-((R-3-mercapto-2-((2-mercapto ethyl)thio)propyl)thio)propyl)thio)-2-((2-mercaptoethyl)thio)propane-1-thiol)(译注:此处括号原文如此,下同 )、3,3'-二硫代二(丙烷-1,2-二硫醇)(3,3'-dithio bis(propane-1,2-dithiol))、(7R,11S)-7,11-二(巯基甲基)-3,6,9,12,15-五硫代十七烷一百烷-1,17-二硫醇((7R,11S)-7,11-bis(mercapto methyl)-3,6,9,12,15-Penta thia heptadecane-1,17-dithiol)、(7R,12S)-7,12-二(巯基甲基)-3,6,9,10,13,16-六硫代十八烷-1,18-二硫醇((7R,12S)-7,12-bis(mercapto methyl)-3,6,9,10,13,16-hexa thia octadecane-1,18-dithiol)、5,7-二巯基甲基-1,11-二巯基-3,6,9-三硫代十一烷(5,7-dimercapto methyl-1,11-dimercapto-3,6,9-trithia undecane)、4,7-二巯基甲基-1,11-二巯基-3,6,9-三硫代十一烷(4,7-dimercapto methyl-1,11-dimercapto-3,6,9-trithia undecane)、4,8-二巯基甲基-1,11-二巯基-3,6,9-三硫代十一烷(4,8-dimercapto methyl-1,11-dimercapto-3,6,9-trithia undecane)、季戊四醇四(3-巯基丙酸酯)(Penta erythritolTetrakis(3-mercapto propionate))、三亚甲醇丙烷三(3-巯基丙酸酯)(trimethylolpropane tris(3-mercapto propionate))、季戊四醇四(2-巯基醋酸盐)(PentaerythritolTetrakis(2-mercapto acetate))、二季戊四醇-乙醚-苯丙锡(3-巯基丙酸酯)(bispentaerythritol-ether-hexakis(3-mercapto propionate))、1,1,3,3-四(巯基甲基硫代)丙烷(1,1,3,3-Tetrakis(mercapto methyl thio)propane)、1,1,2,2-四(巯基甲基硫代)乙烷(1,1,2,2-Tetrakis(mercapto methyl thio)ethane)、4,6-二(巯基甲基硫代)-1,3-二噻烷(4,6-bis(mercapto methyl thio)-1,3-dithiane)及2-(2,2-二(巯基二甲基硫代)乙基)-1,3-二噻烷(2-(2,2-bis(mercapto dimethyl thio)ethyl)-1,3-dithiane)等。之外,只要是具有1个以上硫醇基的化合物,即可以使用一种或者混合使用2种以上。另外,也可以使用向聚硫醇化合物添加异氰酸酯或硫代环氧基化合物、硫化环丙烷(Thietane)或以树脂改性剂使用的带不饱和结合的化合物,通过预聚合得到的聚合变性产物。作为聚硫醇化合物最好是向二(2-巯基乙基)硫化物或二(2-巯基乙基)硫化物混合1种以上其他聚硫醇化合物使用。
所述聚合性合成物还可以包括聚异氰酸酯化合物。所述聚异氰酸酯化合物没有特别限制,可以使用至少带1个以上异氰酸及/.或异硫代氰酸基的化合物。比如,可以混合使用1种或2种以上2,2-二甲基戊烷二异氰酸酯(2,2-dimethyl pentane diisocyanate)、2,2,4-三甲基己烷二异氰酸酯(2,2,4-trimethyl hexane diisocyanate)、六亚甲基二异氰酸酯(hexa methylene diisocyanate)、五亚甲基二异氰酸酯(Penta methylenediisocyanate)、丁烯二异氰酸酯(butene diisocyanate)、1,3-丁二烯-1,4-二异氰酸酯(1,3-butadiene-1,4-diisocyanate)、2,4,4-三甲基六亚甲基二异氰酸酯(2,4,4-trimethyl hexa methylene diisocyanate)、1,6,11-十一烷三异氰酸酯(1,6,11-undecane triisocyanate)、1,3,6-六亚甲基三异氰酸酯(1,3,6-hexa methylenetriisocyanate)、1,8-二异氰酸酯-4-异氰酸基甲基辛烷(1,8-diisocyanate-4-isocyanato methyl octane)、二(异氰酸基乙基)碳酸酯(bis(isocyanato ethyl)carbonate)、二(异氰酸基乙基)乙醚(bis(isocyanato ethyl)ether)等脂肪族异氰酸酯化合物(aliphatic isocyanate compounds);异佛尔酮二异氰酸酯(isophoronediisocyanate)、1,2-二(异氰酸基甲基)环己烷(1,2-bis(isocyanato methyl)cyclohexane)、1,3-二(异氰酸基甲基)环己烷(1,3-bis(isocyanato methyl)cyclo hexane)、1,4-二(异氰酸基甲基)环己烷(1,4-bis(isocyanato methyl)cyclo hexane)、二环己基甲烷二异氰酸酯(dicyclo hexyl methane diisocyanate)、环己烷二异氰酸酯(cyclo hexanediisocyanate)、甲基环己烷二异氰酸酯(methyl cyclo hexane diisocyanate)、二环己基二甲基甲烷异氰酸酯(dicyclo hexyl dimethyl methane isocyanate)、2,2-二甲基二环己基甲烷异氰酸酯(2,2-dimethyl dicyclo hexyl methane isocyanate)等脂环族异氰酸酯化合物(Cycloaliphatic isocyanate compounds);亚二甲苯基二异氰酸酯(xylylenediisocyanate(XDI)),二(异氰酸基乙基)苯(bis(isocyanatoethyl)benzene)、二(异氰酸基丙基)苯(bis(isocyanato propyl)benzene)、二(异氰酸基丁基)苯(bis(isocyanatobutyl)benzene)、二(异氰酸基甲基)萘(bis(isocyanato methyl)naphthalene)、二(异氰酸基甲基)二苯基乙醚(bis(isocyanato methyl)diphenyl ether)、亚苯基二异氰酸酯(phenylene diisocyanate)、乙基亚苯基二异氰酸酯(ethyl phenylene diisocyanate)、异丙基亚苯基二异氰酸酯(isopropyl phenylene diisocyanate)、二甲基亚苯基二异氰酸酯(dimethyl phenylene diisocyanate)、二乙基亚苯基二异氰酸酯(diethyl phenylenediisocyanate)、二异丙基亚苯基二异氰酸酯(diisopropyl phenylene diisocyanate)、三甲基苯三异氰酸酯(trimethyl benzene triisocyanate)、苯三异氰酸酯(benzenetriisocyanate)、联苯二异氰酸酯(biphenyl diisocyanate)、甲苯胺二异氰酸酯(toluidine diisocyanate)、4,4-二苯基甲烷二异氰酸酯(4,4-diphenyl methanediisocyanate)、3,3-二甲基二苯基甲烷-4,4-二异氰酸酯(3,3-dimethyl diphenylmethane-4,4-diisocyanate)、联苄-4,4-二异氰酸酯(bibenzyl-4,4-diisocyanate)、二(异氰酸基苯基)乙烯(bis(isocyanato phenyl)ethylene)、3,3-二甲氧基联苯-4,4-二异氰酸酯(3,3-dimethoxy biphenyl-4,4-diisocyanate)、六氢苯二异氰酸酯(hexahydrobenzene diisocyanate)、六氢二苯基甲烷-4,4-二异氰酸酯(hexa hydro diphenylmethane-4,4-diisocyanate)等芳香族异氰酸酯化合物(aromatic isocyanatecompounds);二(异氰酸基乙基)硫化物(bis(isocyanato ethyl)sulphide)、二(异氰酸基丙基)硫化物(bis(isocyanato propyl)sulphide)、二(异氰酸基己基)硫化物(bis(isocyanato hexyl)sulphide)、二(异氰酸基甲基)硫化物(bis(isocyanato methyl)sulfide)、二(异氰酸基甲基)二硫化物(bis(isocyanato methyl)disulphide)、二(异氰酸基丙基)二硫化物(bis(isocyanato propyl)disulphide)、二(异氰酸基甲基硫代)甲烷(bis(isocyanato methyl thio)methane)、二(异氰酸基乙基硫代)甲烷(bis(isocyanatoethyl thio)methane)、二(异氰酸基乙基硫代)乙烷(bis(isocyanato ethyl thio)ethane)、二(异氰酸基甲基硫代)乙烷(bis(isocyanato methyl thio)ethane)、1,5-二异氰酸基-2-异氰酸基甲基-3-硫代戊烷(1,5-diisocyanato-2-isocyanato methyl-3-thiapentane)等含硫脂肪族异氰酸酯化合物(sulfur aliphatic isocyanate compounds);二苯基硫化物-2,4-二异氰酸酯(diphenyl sulphide-2,4-diisocyanate)、二苯基硫化物-4,4-二异氰酸酯(diphenyl sulphide-4,4-diisocyanate)、3,3-二甲氧基-4,4-二异氰酸基二苯甲基硫代乙醚(3,3-dimethoxy-4,4-diisocyanato dibenzyl thio ether)、二(4-异氰酸基甲基苯)硫化物(bis(4-isocyanato methyl benzene)sulphide)、4,4-甲氧基苯硫代乙烯乙二醇-3,3-二异氰酸酯(4,4-methoxy benzene thio ethylene glycol-3,3-diisocyanate)、二苯基二硫化物-4,4-二异氰酸酯(diphenyl disulphide-4,4-diisocyanate)、2,2-二甲基二苯基二硫化物-5,5-二异氰酸酯(2,2-dimethyl diphenyldisulphide-5,5-diisocyanate)、3,3-二甲基二苯基二硫化物-5,5-二异氰酸酯(3,3-dimethyl diphenyl disulphide-5,5-diisocyanate)、3,3-二甲基二苯基二硫化物-6,6-二异氰酸酯(3,3-dimethyl diphenyl disulphide-6,6-diisocyanate)、4,4-二甲基二苯基二硫化物-5,5-二异氰酸酯(4,4-dimethyl diphenyl disulphide-5,5-diisocyanate)、3,3-二甲氧基二苯基二硫化物-4,4-二异氰酸酯(3,3-dimethoxy diphenyl disulphide-4,4-diisocyanate)、4,4-二甲氧基二苯基二硫化物-3,3-二异氰酸酯(4,4-dimethoxydiphenyl disulphide-3,3-diisocyanate)等含硫芳香族异氰酸酯化合物(sulfuraromatic isocyanate compounds);2,5-二异氰酸基噻吩(2,5-diisocyanatothiophene)、2,5-二(异氰酸基甲基)噻吩(2,5-bis(isocyanato methyl)thiophene)、2,5-二异氰酸基四氢噻吩(2,5-diisocyanato Tetra hydrothiophene),2,5-二(异氰酸基甲基)四氢噻吩(2,5-bis(isocyanato methyl)Tetra hydrothiophene)、3,4-二(异氰酸基甲基)四氢噻吩(3,4-bis(isocyanato methyl)Tetra hydrothiophene)、2,5-二异氰酸基-1,4-二噻烷(2,5-diisocyanato-1,4-dithiane)、2,5-二(异氰酸基甲基)-1,4-二噻烷(2,5-bis(isocyanato methyl)-1,4-dithiane)、4,5-二异氰酸基-1,3-二噻茂烷(4,5-diisocyanato-1,3-dithiolane)、4,5-二(异氰酸基甲基)-1,3-二噻茂烷(4,5-bis(isocyanato methyl)-1,3-dithiolane)、4,5-二(异氰酸基甲基)-2-甲基-1,3-二噻茂烷(4,5-bis(isocyanato methyl)-2-methyl-1,3-dithiolane)等含硫杂环异氰酸酯化合物(sulfur heterocyclic isocyanate compounds)。还可以使用这些化合物的氯取代产物(substitution product)、溴取代产物等卤族取代产物、烷基取代产物(alkylsubstitution product)、烷氧基取代产物(alkoxy substitution product)、硝基取代产物(nitro substitution product)或与多价醇或硫醇的预聚物(prepolymer)型变性产物(denaturant)、碳化二亚胺(carbodiimide)变性产物、尿素(urea)变性产物、缩二脲(biuret)变性产物或二聚物(dimer)化或三聚物(trimer)化反应生成物等。作为聚异氰酸酯化合物最好是使用选自异佛尔酮二异氰酸酯、六亚甲基二异氰酸酯、环己烷二异氰酸酯的1种以上。
所述聚合合成物为了提高光学材料的光学物性,以调节耐冲击性能、比重及单体(monomer)粘度等为目的,作为树脂改性剂可以额外添加烯烃化合物。可作为反应性树脂改性剂添加的烯烃(olefin)化合物,比如有丙烯酸苄基酯(benzylacrylate)、苄基甲基丙烯酸脂(benzylmethacrylate)、丁氧基乙烷基丙烯酸脂(butoxy ethylacrylate)、丁氧基甲基甲基丙烯酸脂(butoxy methyl methacrylate)、环己基丙烯酸脂(cyclo hexylacrylate)、环己基甲基丙烯酸脂(cyclo hexyl methacrylate)、2-羟基乙烷基丙烯酸脂(2-hydroxyl ethylacrylate)、2-羟甲基甲基丙烯酸脂(2-hydroxyl methylmethacrylate)、环氧丙基丙烯酸脂(glycidyl acrylate)、环氧丙基甲基丙烯酸脂(glycidyl methacrylate)、苯氧基乙烷基丙烯酸脂(phenoxy ethylacrylate)、苯氧基乙烷基甲基丙烯酸脂(phenoxy ethylmethacrylate)、苯基甲基丙烯酸脂(phenylmethacrylate)、乙烯乙二醇二丙烯酸脂(ethylene glycol diacrylate)、乙烯乙二醇二甲基丙烯酸脂(ethylene glycol dimethacrylate)、二乙烯乙二醇二丙烯酸脂(diethylene glycol diacrylate)、二乙烯乙二醇二甲基丙烯酸脂(diethylene glycoldimethacrylate)、三乙烯乙二醇二丙烯酸脂(triethylene glycol diacrylate),三乙烯乙二醇二甲基丙烯酸脂(triethylene glycol dimethacrylate)、四乙烯乙二醇二丙烯酸脂(tetra ethylene glycol diacrylate)、四乙烯乙二醇二甲基丙烯酸脂(tetraethylene glycol dimethacrylate)、聚乙烯乙二醇二丙烯酸脂(polyethylene glycoldiacrylate)、聚乙烯乙二醇二甲基丙烯酸脂(polyethylene glycol dimethacrylate)、新戊基乙二醇二丙烯酸脂(neopentyl glycol diacrylate)、新戊基乙二醇二甲基丙烯酸脂(neopentyl glycol dimethacrylate)、乙烯乙二醇二环氧丙基丙烯酸脂(ethyleneglycol bisglycidyl acrylate)、乙烯乙二醇二环氧丙基甲基丙烯酸脂(ethylene glycolbisglycidyl methacrylate)、二苯酚A二丙烯酸脂(bisphenol A diacrylate)、二苯酚A二甲基丙烯酸脂(bisphenol A dimethacrylate)、2,2-二(4-烯丙氧乙氧基苯基)丙烷(2,2-bis(4-acryloxy ethoxy phenyl)propane)、2,2-二(4-甲基烯丙氧乙氧基苯基)丙烷(2,2-bis(4-methacryloxy ethoxy phenyl)propane)、2,2-二(4-烯丙氧二乙氧基苯基)丙烷(2,2-bis(4-acryloxy diethoxy phenyl)propane)、2,2-二(4-甲基乙氧基二乙氧基苯基)丙烷(2,2-bis(4-methacryloxydiethoxy phenyl)propane)、二苯酚F二丙烯酸脂(bisphenolF diacrylate)、二苯酚F二甲基丙烯酸脂(bisphenol F dimethacrylate)、1,1-二(4-烯丙氧乙氧基苯基)甲烷(1,1-bis(4-acryloxy ethoxy phenyl)methane)、1,1-二(4-甲基烯丙氧乙氧基苯基)甲烷(1,1-bis(4-methacryloxy ethoxy phenyl)methane)、1,1-二(4-烯丙氧二乙氧基苯基)甲烷(1,1-bis(4-acryloxy diethoxy phenyl)methane)、1,1-二(4-甲基乙氧基二乙氧基苯基)甲烷(1,1-bis(4-methacryloxydiethoxy phenyl)methane)、二羟甲基三三环癸烷二丙烯酸脂(dimethylol tricyclo decane diacrylate)、三羟甲基丙烷三丙烯酸脂(trimethylol propane triacrylate)、三羟甲基丙烷三甲基丙烯酸脂(trimethylol propane trimethacrylate)、丙三醇二丙烯酸脂(glycerol diacrylate)、丙三醇二甲基丙烯酸脂(glycerol dimethacrylate)、五赤藓糖醇三丙烯酸脂(Pentaerythritol triacrylate)、五赤藓糖醇四丙烯酸脂(Penta erythritol tetraacrylate)、五赤藓糖醇四甲基丙烯酸脂(Penta erythritol tetra methacrylate)、甲基硫代丙烯酸脂(methyl thio acrylate)、甲基硫代甲基丙烯酸脂(methyl thiomethacrylate)、苯基硫代丙烯酸脂(phenylthio acrylate)、苄基硫代甲基丙烯酸脂(benzylthio methacrylate)、苯二甲基二硫醇二丙烯酸脂(xylylene dithioldiacrylate)、苯二甲基二硫醇二甲基丙烯酸脂(xylylene dithiol dimethacrylate)、巯基乙烷基硫化物二丙烯酸脂(mercapto ethylsulfide diacrylate)、巯基乙烷基硫化物二甲基丙烯酸脂(mercapto ethylsulfide dimethacrylate)等(甲基)丙烯酸脂((meth)acrylate)化合物及、烯丙基环氧丙基醚(allyl glycidyl ether)、二烯丙基邻苯二甲酸酯(diallyl phthalate)、二烯丙基对苯二酸酯(diallyl terephthalate)、二烯丙基间苯二酸酯(diallyl isophthalate)、二烯丙基碳酸酯(diallyl carbonate)、二乙烯乙二醇二烯丙基碳酸酯(diethylene glycol bisallyl carbonate)等烯丙基(allyl)化合物、苯乙烯(styrene)、氯苯乙烯(chlorostyrene)、甲基苯乙烯(methyl styrene)、溴代苯乙烯(bromostyrene)、二溴代苯乙烯(dibromostyrene)、二乙烯基苯(divinyl benzene)、3,9-二乙烯基螺二(甲基-二环氧乙烷)(3,9-divinyl Spiro bi(meth-dioxane))等乙烯基(vinyl)化合物,但可使用的化合物不局限于上面示例的化合物。这些烯烃(olefin)化合物可以单独或混合2种以上使用。
除此之外,本发明的聚合合成物按公知的成型方法,可以包括各种添加剂,比如扩链剂(chain extender)、交联剂(cross linking agent)、聚合引发剂(polymerizationinitiator)、内部脱模剂、光稳定剂、热稳定剂、防氧化剂、紫外线吸收剂、着色防止剂、有机颜料、无机颜料、填充剂、粘合性增强剂等各种添加剂。
作为内部脱模剂可以单独或混合2种以上使用磷酸酯化合物、硅胶系列界面活性剂、氟系列界面活性剂,内部脱模剂最好是相对于聚合合成物的重量,含0.001~10重量%。作为内部脱模剂最好是使用磷酸酯化合物。磷酸酯化合物通过向五氧化二磷(P2O5)添加2~3摩尔的醇化合物制造。这里,按使用的醇种类,可以获得多种形式磷酸酯化合物。代表性的有向脂肪族醇添加环氧乙烷或环氧丙烷,或者向壬基苯酚(nonylphenol)基等添加环氧乙烷或环氧丙烷的种类。本发明的聚合性合成物作为内部脱模剂使用添加环氧乙烷或环氧丙烷的磷酸酯化合物时,可以得到脱模性好、品质优秀的光学材料。作为内部脱模剂使用的磷酸酯化合物最好是从聚氧化乙烯壬基苯酚醚磷酸酯(poly oxy ethylene nonyl phenolether phosphate)(添加环氧乙烷5摩尔的5重量%,添加4摩尔的80重量%,添加3摩尔的10重量%,添加1摩尔的5重量%),聚氧化乙烯壬基苯酚醚磷酸酯(添加环氧乙烷9摩尔的3重量%,添加8摩尔的80重量%,添加9摩尔的5重量%,添加7摩尔的6重量%,添加6摩尔的6重量%),聚氧化乙烯壬基苯酚醚磷酸酯(添加环氧乙烷13摩尔的3重量%,添加12摩尔的80重量%,添加11摩尔的8重量%,添加9摩尔的3重量%,添加4摩尔的6重量%),聚氧化乙烯壬基苯酚醚磷酸酯(添加环氧乙烷17摩尔的3重量%,添加16摩尔的79重量%,添加15摩尔的10重量%,添加14摩尔的4重量%,添加13摩尔的4重量%),聚氧化乙烯壬基苯酚醚磷酸酯(添加环氧乙烷21摩尔的5重量%,添加20摩尔的76重量%,添加19摩尔的7重量%,添加18摩尔的6重量%,添加17摩尔的4重量%)等添加有环氧乙烷或环氧丙烷的磷酸酯化合物中选择1种或2种以上使用。
紫外线吸收剂相对于整个单体重量,添加0.005~6重量%(50~60,000ppm),最好是添加0.01~3重量%(100~30,000ppm)。紫外线吸收剂的添加量不足0.005重量%时,很难得到有效的紫外线吸收性能,镜片暴露紫外线时,变黄问题非常严重。另外,含量为6重量%以上时,很难溶解于合成物,而且在硬化过程中会引发很多聚合不良。作为紫外线吸收剂,可以无限制使用可在眼镜镜片使用的公知的紫外线吸收剂。比如,可单独或混合2种以上使用2-(2'-羟基-5-甲基苯基)-2H-苯并三唑(2-(2'-hydroxyl-5-methyl phenyl)-2H-Benzotriazol);2-(2'-羟基-3',5'-二-t-丁基苯基)-5-氯-2H-苯并三唑(2-(2'-hydroxyl-3',5'-di-t-butyl phenyl)-5-chloro-2H-Benzotriazol);2-(2'-羟基-3'-t-丁基-5'-甲基苯基)-5-氯-2H-苯并三唑(2-(2'-hydroxyl-3'-t-butyl-5'-methylphenyl)-5-chloro-2H-Benzotriazol);2-(2'-羟基-3',5'-二-t-戊基苯基)-2H-苯并三唑(2-(2'-hydroxyl-3',5'-di-t-amyl phenyl)-2H-Benzotriazol);2-(2'-羟基-3',5'-二-t-丁基苯基)-2H-苯并三唑(2-(2'-hydroxyl-3',5'-di-t-butyl phenyl)-2H-Benzotriazol);2-(2'-羟基-5'-t-丁基苯基)-2H-苯并三唑(2-(2'-hydroxyl-5'-t-butylphenyl)-2H-Benzotriazol);2-(2'-羟基-5'-t-辛基苯基)-2H-苯并三唑(2-(2'-hydroxyl-5'-t-octyl phenyl)-2H-Benzotriazol);2,4-二羟基苯甲酮(2,4-dihydroxylbenzophenone);2-羟基-4-甲氧苯甲酮(2-hydroxyl-4-methoxy benzophenone);2-羟基-4-辛氧苯甲酮(2-hydroxyl-4-octyl oxybenzophenone);4-十二氧-2-羟基苯甲酮(4-dodecyl oxy-2-hydroxyl benzophenone);4-苯并氧-2-羟基苯甲酮(4-benzo oxy-2-hydroxyl benzophenone);2,2',4,4'-四羟基苯甲酮(2,2',4,4'-tetra hydroxylbenzophenone);2,2'-二羟基-4,4'-二甲氧苯甲酮(2,2'-dihydroxyl-4,4'-dimethoxybenzophenone)。最好是使用在400nm以下波长领域具有良好紫外线吸收能力,与本发明的合成物呈现良好溶解性能的2-(2'-羟基-5'-t-辛基苯基)-2H-苯并三唑或2,2'-二羟基-4,4'-二甲氧苯甲酮等。
作为有机颜料可以使用公知的有机颜料。本发明的一实施例使用了京仁洋行(株)公司的1-羟基-4-(p-甲苯胺)蒽醌[1-hydroxy-4-(p-toludine)anthraquinone],芘酮染料(perinone dye)等。这种有机颜料按每1kg单体添加0.5~10,000ppm,最好是5~1000ppm,可以通过紫外线吸收剂防止光学镜片变黄。
聚合引发剂(催化剂)对硬化起重要的作用。催化剂的种类通常使用环氧硬化剂,但强胺类会让异氰酸酯剧烈反应,使用时应多加注意。本发明主要使用胺的酸盐类、鏻盐(phosphonium salt)类、磷化氢(phosphine)类及带吸电子基(electron withdrawinggroup)的三级胺类、路易斯酸(Lewis acid)类、自由基引发剂(radical initiators)等,催化剂的种类和使用量,可由一般技术人员适当选择。使用量最好是相对于整个单体重量,使用0.001~5重量%。
作为胺(amine)系有三乙烷基胺(triethylamine)、三丙基胺(tripropyl amine)、二丙基乙烷基胺(dipropyl ethylamine)、三丁基胺(tributyl amine)、三己基胺(trihexyl amine)、二甲基环己基胺(dimethyl cyclo hexyl amine)、二环己基乙烷基胺(dicyclo hexyl ethylamine)、三环己基胺(tricyclo hexyl amine)、二乙烷基环己基胺(diethylcyclo hexyl amine)、二环己基乙烷基胺(dicyclo hexyl ethylamine)、二丙基环己基胺(dipropyl cyclo hexyl amine)、二环己基丙基胺(dicyclo hexyl propylamine)、二丁基环己基胺(dibutyl cyclo hexyl amine)、二环己基丁炔胺(dicyclo hexylbutyne amine)、N,N-二甲基苄基胺(N,N-dimethyl benzylamine)、N,N-二乙烷基苄基胺(N,N-diethylbenzylamine)、N,N-二丙基苄基胺(N,N-dipropyl benzylamine)、N,N-二丁基苄基胺(N,N-dibutyl benzylamine)、N-甲基苄基胺(N-methyl benzylamine)、2-二甲基氨基甲基苯酚(2-dimethyl amino methyl phenol)、2,4,6-三(N,N-二甲基氨基甲基)苯酚(2,4,6-tris(N,N-dimethyl amino methyl phenol)、三乙烯二胺(triethylenediamine)、四甲基乙烯二胺(tetra methyl ethylene diamine)、四乙烷基乙烯二胺(tetraethylethylene diamine)、N,N-二甲基环己基胺(N,N-dimethyl cyclo hexyl amine)、N,N-二环己基甲基胺(N,N-dicyclo hexyl methyl amine)、四丙基乙烯二胺(tetra propylethylene diamine)、四丁基乙烯二胺(tetra butyl ethylene diamine)、五甲基二乙烯三胺(Penta methyl diethylene triamine)、五乙烷基二乙烯三胺(Penta ethyldiethylenetriamine)、五丙基二乙烯三胺(Penta propyl diethylene triamine)、五丁基二乙烯三胺(Penta butyl diethylene triamine)、N-甲基哌啶(N-methyl piperidine)、N-乙烷基哌啶(N-ethylpiperidine)、N-丙基哌啶(N-propyl piperidine)、N-丁基哌啶(N-butylpiperidine)、N,N-二甲基哌嗪(N,N-dimethyl piperazine)、N,N-二乙烷基哌嗪(N,N-diethylpiperazine)、N,N-二丙基哌嗪(N,N-dipropyll piperazine)、N,N-二丁基哌嗪(N,N-dibutyl piperazine)、六亚甲基四胺(hexa methylene tetramine)、二甲基氨基乙烷基醋酸酯(dimethyl amino ethylacetate)、二乙烷基氨基乙烷基醋酸酯(diethylaminoethylacetate)、二甲基氨基丙腈(dimethyl amino propionitrile)、二乙烷基氨基丙腈(diethylamino propionitrile)、N-甲基吗琳(N-methyl morpholine)、N-乙烷基吗琳(N-ethylmorpholine)、N-丙基吗琳(N-propyl morpholine)、N-丁基吗琳(N-butylmorpholine)、N-环己基吗琳(N-cyclo hexyl morpholine)、N-甲基哌啶酮(N-methylpiperidone)、N-乙烷基哌啶酮(N-ethylpiperidone)、N-丙基哌啶酮(N-propylpiperidone)、N-丁基哌啶酮(N-butyl piperidone)、N-甲基吡咯烷(N-methylpyrrolidine)、N-乙烷基吡咯烷(N-ethylpyrrolidine)、N-丙基吡咯烷(N-propylpyrrolidine)、N-丁基吡咯烷(N-butyl pyrrolidine)、N-甲基吡咯烷酮(N-methylpyrrolidone)、N-乙烷基吡咯烷酮(N-ethylpyrrolidone)、N-丙基吡咯烷酮(N-propylpyrrolidone)及N-丁基吡咯烷酮(N-butyl pyrrolidone)等。作为芳香族三级胺(tertiaryamine),有N,N-二甲基苯胺(N,N-dimethyl aniline)、N,N-二乙烷基苯胺(N,N-diethylaniline)、N,N-二丙基苯胺(N,N-dipropyl aniline)、N,N-二丁基苯胺(N,N-dibutyl aniline)、N,N-环己基甲基苯胺(N,N-cyclo hexyl methyl aniline)、N,N-二环己基苯胺(N,N-dicyclo hexyl aniline)、二苯基甲基胺(diphenylmethyl amine)、二苯基乙烷基胺(diphenylethylamine)、三苯基胺(triphenylamine)、N,N-二甲基甲苯胺(N,N-dimethyl toluidine)、N,N-二乙烷基甲苯胺(N,N-diethyltoluidine)、N-环己基-N-甲基甲苯胺(N-cyclo hexyl-N-methyl toluidine)、N,N-二环己基甲苯胺(N,N-dicyclo hexyltoluidine)、N,N-二甲基萘基胺(N,N-dimethyl naphthyl amine)、N,N-二乙烷基萘基胺(N,N-diethyl naphthyl amine)、N,N-二甲基茴香胺(N,N-dimethyl anisidine)、N,N-二乙烷基茴香胺(N,N-diethylanisidine)及N,N,N`,N`-四甲基亚苯基二胺(N,N,N`,N`-tetra methyl phenylenediamine)等。可以使用吡啶(pyridine)、甲基吡啶(picoline)、二甲基吡啶(dimethyl pyridine)、2,2'-二吡啶(2,2'-bipyridine)、4,4'-二吡啶(4,4'-bipyridine)、吡啶(pyrazole)、N-甲基吡唑(N-methyl pyrazole)、N-乙烷基吡唑(N-ethylpyrazole)、N-丙基吡唑(N-propyl pyrazole)、N-丁基吡唑(N-butyl pyrazole)、N-环己基吡唑(N-cyclohexyl pyrazole)、哒嗪(pyridazine)、嘧啶(pyrimidine)、吡咯啉(pyrroline)、恶唑(oxazole)、噻唑(thiazole)、1-甲基咪唑(1-methyl imidazole)、1-苄基咪唑(1-benzylimidazole)、1-甲基-2-甲基咪唑(1-methyl-2-methyl imidazole)、1-苄基-2-甲基咪唑(1-benzyl-2-methyl imidazole)、1-乙烷基-4-甲基咪唑(1-ethyl-4-methyl imidazole)、1-乙烷基-2-乙烷基-4-亚甲醇(1-ethyl-2-ethyl-4-methylol)、N-甲基吡咯(N-methyl pyrrol)、N-乙烷基吡咯(N-ethylpyrrol)、N-丁基吡咯(N-butylpyrrol)、N-甲基吡咯啉(N-methyl pyrroline)、N-乙烷基吡咯啉(N-ethylpyrroline)、N-丁基吡咯啉(N-butyl pyrroline)、嘧啶(pyrimidine)、嘌呤(purine)、喹啉(quinoline)、异喹啉(isoquinoline)、N-甲基咔唑(N-methyl carbazole)、N-乙烷基咔唑(N-ethylcarbazole)及N-丁基咔唑(N-butyl carbazole)等。另外,作为锡系化合物,单独使用或同时使用2种以上丁基锡二十二酸酯(butyltin dilaurate);二丁基锡二氯化物(dibutyltin dichloride);二丁基锡二醋酸酯(dibutyltin diacetate);辛基酸(octylacid)第1锡(tin);二十二烷酸二丁基锡(dilauric acid dibutyltin);四氟代锡(tetra fluoro tin);四氯锡(tetra chlorotin);四溴代锡(tetra bromotin);四碘代锡(tetra iodide tin);甲基锡三氯化物(methyl tin trichloride);丁基锡三氯化物(butyl tin trichloride);二甲基锡二氯化物(dimethyl tin dichloride);二丁基锡二氯化物(dibutyl tin dichloride);三甲基锡氯化物(trimethyl tin chloride);三丁基锡氯化物(tributyl tin chloride);三苯基锡氯化物(triphenyltin chloride);二丁基锡硫化物(dibutyl tin sulfide);二(2-乙烷基己基)锡氧化物(di(2-ethylhexyltinoxide)。
路易斯酸比如有氯化锌(zinc chloride)、乙酰丙酮锌(zinc acetylacetone)及二丁基氨基甲酸锌(zinc dibuty dicarbamic)等锌系列化合物;氯化铁及乙酰丙酮铁等铁系列化合物;铝、氟化铝、氯化铝及三苯基(triphenyl)铝等铝系列化合物。
以上述方法制造聚合性合成物后,通过注模聚合获得光学材料。把聚合合成物注入由密封件或胶带封好的模具之间,进行聚合反应。聚合条件按聚合性合成物、催化剂的种类和用量,模具的形状呈现很大差别,因此没有限定,但在约-50~150℃温度下,经1~50小时进行。有时根据情况,在10~150℃温度范围下维持或逐渐升温,经1~48小时进行硬化为宜。通过硬化得到的光学材料,根据需要可以进行退火等处理。处理温度通常为50~150℃,最好是90~140℃。
本发明的光学材料,通过更换注模聚合时的模具,可以获得多种形状的成型体,可作为眼镜镜片、相机镜片、发光二极管(LED)等各种光学材料使用。尤其适合作为眼镜镜片、相机镜片、发光二极管等的光学材料、光学元件使用。
通过本发明获得的光学镜片,可根据需要在两面形成涂层。作为涂层有底漆(primer)层、硬皮层、防反射层、防雾层、防污染层、防水层。这些涂层可以分别单独形成,或多层形成多个涂层。在两面实施涂层时,两面分别形成不同的涂层或相同的涂层。本发明的光学镜片可以利用分散颜料或光变颜料进行着色处理后使用。
【实施例】
为使本发明实施例的目的、技术方案和优点更加清楚,下面将结合本发明实施例中的附图,对本发明实施例中的技术方案进行清楚、完整的描述,显然,所描述的实施例是本发明一部分实施例,而不是全部的实施例。基于本发明中的实施例,本领域普通技术人员在没有作出创造性劳动前提下所获得的所有其他实施例,都属于本发明保护的范围。
物性实验方法
以如下实验方法对实施例制造的光学镜片检测物性,结果如下表1所示。
1)屈光率及阿贝数:使用了Atago Co.,公司的DR-M4型号阿贝屈光计。
2)聚合不均匀:用肉眼观察通过工序获得的镜片100只,如发生3个以上脉理、白化、边缘气泡,则记录“X”,如没有发生则记录“0”。
3)硬化状态:没有硬化或出现激烈反应、导致硬化不正常时记录“X”,如硬化良好、生成无色固态树脂,则记录“0”。
4)玻璃转换温度(Tg:glass transition temperature):以TMAQ400(TAInstruments)的穿透法(0.8N重荷、针尖0.5mmΦ、升温温度5℃/min),在高纯度氮中检测了TMA。
合成例1:二(3-氯-2-羟丙基)硫化物(bis(3-chloro-2-hydroxylpropyl)
sulfide)的合成
向10升反应器添加表氯醇(epichlorohydrin)(5563g,60.12mol)及甲醇(2500g)后,把反应温度调节为6℃,当反应温度到达6℃时添加苛性钠(caustic soda)(50%aq,5g)。向另一10升反应器中加入NaSH.xH2O(70%NaSH,3660g,45.75mol)、甲醇(1000g)及水(500g),通过搅拌完全融化后,慢慢滴加盐酸,把生成的硫化氢添加到表氯醇溶液,获得了二(3-氯-2-羟丙基)硫化物。反应的结束点为通过GC确认最终生成物,表氯醇和3-氯-2-羟基-丙基-1-硫醇化合物完全消失,二(3-氯-2-羟丙基)硫化物生成的时间点。如存在3-氯-2-羟基-丙基-1-硫醇,则通过GC计算相对含量,通过添加表氯醇,进行反应,获得二(3-氯-2-羟丙基)硫化物。生成物几乎得到了99%以上收率,纯度为95%。
合成例2:二-(2,3-环硫代丙基)硫化物的合成(pH2.5)
向10升反应容器添加二(3-氯-2-羟丙基)硫化物(1072.48g,4.89mol)、甲苯(toluene)1300g、甲醇800g,进行搅拌,把反应温度调到30℃。到达25℃时,滴加NaOH(50%aq.,783.08g,9.78mol),滴加时的反应温度进行在35~37℃,维持温度、进行反应。滴加进行在1小时以内,之后在37℃条件下放置约30分钟发酵,发酵结束后,添加甲苯2000g,约搅拌10分钟,进行分层,以水对上清液有机物进行2次清洗,最大限度去除水分,向有几层有机溶液再次添加甲醇400g、进行搅拌,在反应温度8℃下添加硫脲素(thiourea)(1117.65g,14.30mol)及无水醋酸(70g),把反应温度调高到18℃,反应18小时。反应结束点通过HPLC确认,出发物质小时,生成物没有进一步变化为准。反应结束后,停止搅拌,以水清洗3次通过层分离获得的有几层,向所获有几层添加10%硫酸,去除有机溶剂,获得pH为2.5的二-(2,3-环硫代丙基)硫化物。测得屈光率(nD,20℃)为1.614。
合成例3:二-(2,3-环硫代丙基)硫化物的合成(pH3.5)
向10升反应容器添加二(3-氯-2-羟丙基)硫化物(1072.48g,4.89mol)、甲苯(toluene)1300g、甲醇800g,进行搅拌,把反应温度调到25℃。到达25℃时,滴加NaOH(50%aq.,783.08g,9.78mol),滴加时的反应温度进行在35~37℃,维持温度、进行反应。滴加进行在1小时以内,之后在37℃条件下放置约30分钟发酵,发酵结束后,添加甲苯2000g,约搅拌10分钟,进行分层,以水对上清液有机物进行2次清洗,最大限度去除水分,向有几层有机溶液再次添加甲醇400g、进行搅拌,在反应温度8℃下添加硫脲素(thiourea)(1117.65g,14.30mol)及无水醋酸(70g),把反应温度调高到18℃,反应18小时。反应结束点通过HPLC确认,出发物质小时,生成物没有进一步变化为准。反应结束后,停止搅拌,以水清洗3次通过层分离获得的有几层,向所获有几层添加5%硫酸,去除有机溶剂,获得pH为3.5的二-(2,3-环硫代丙基)硫化物。测得屈光率(nD,20℃)为1.614。
合成例4:二-(2,3-环硫代丙基)硫化物的合成(pH5.0)
向10升反应容器添加二(3-氯-2-羟丙基)硫化物(1072.48g)、甲苯(toluene)1300g、甲醇800g,进行搅拌,把反应温度调到25℃。到达25℃时,滴加NaOH(50%aq.,783.08g),滴加时的反应温度维持在37℃,进行反应。滴加进行在1小时以内,之后在37℃条件下放置约30分钟发酵,发酵结束后,添加甲苯2000g,约搅拌30分钟,进行分层,以1g盐酸溶液中和上清液有机溶液,最大限度去除水分,向有几层有机溶液再次添加甲醇400g、进行搅拌,在反应温度8℃下添加硫脲素(thiourea)(1117.65g)及无水醋酸(70g),把反应温度调高到16.5℃,反应24小时。反应结束点通过HPLC确认,出发物质小时,生成物没有进一步变化为准。反应结束后,停止搅拌,以水清洗3次通过层分离获得的有几层,向所获有几层添加0.1%硫酸,进行清洗,去除有机溶剂,获得pH为5.0的二-(2,3-环硫代丙基)硫化物。测得屈光率(nD,20℃)为1.614。
合成例5:二-(2,3-环硫代丙基)硫化物的合成(pH7.0)
向10升反应容器添加二(3-氯-2-羟丙基)硫化物(1072.48g)、甲苯(toluene)1300g、甲醇800g,进行搅拌,把反应温度调到25℃。到达25℃时,滴加NaOH(50%aq.,783.08g),滴加时的反应温度维持在37℃,进行反应。滴加进行在1小时以内,之后在37℃条件下放置约30分钟发酵,发酵结束后,添加甲苯2000g,约搅拌30分钟,进行分层,以1g盐酸溶液中和上清液有机溶液,最大限度去除水分,向有几层有机溶液再次添加甲醇400g、进行搅拌,在反应温度8℃下添加硫脲素(thiourea)(1117.65g)及无水醋酸(70g),把反应温度调高到16.5℃,反应24小时。反应结束点通过HPLC确认,出发物质小时,生成物没有进一步变化为准。反应结束后,停止搅拌,以水清洗多次通过层分离获得的有几层,去除有机溶剂,获得pH为7.0的二-(2,3-环硫代丙基)硫化物。测得屈光率(nD,20℃)为1.614。
合成例6:二-(2,3-环硫代丙基)硫化物的合成(pH8.0)
向10升反应容器添加二(3-氯-2-羟丙基)硫化物(1072.48g)、甲苯(toluene)1300g、甲醇800g,进行搅拌,把反应温度调到25℃。到达25℃时,滴加NaOH(50%aq.,783.08g),滴加时的反应温度维持在37℃,进行反应。滴加进行在1小时以内,之后在37℃条件下放置约30分钟发酵,发酵结束后,添加甲苯2000g,约搅拌30分钟,进行分层,以1g盐酸溶液中和上清液有机溶液,最大限度去除水分,向有几层有机溶液再次添加甲醇400g、进行搅拌,在反应温度8℃下添加硫脲素(thiourea)(1117.65g)及无水醋酸(70g),把反应温度调高到16.5℃,反应24小时。反应结束点通过HPLC确认,出发物质小时,生成物没有进一步变化为准。反应结束后,停止搅拌,以水清洗3次通过层分离获得的有几层,向获得的有几层添加0.1%氨水,进行清洗,去除有机溶剂,获得pH为8.0的二-(2,3-环硫代丙基)硫化物。测得屈光率(nD,20℃)为1.614。
合成例7:二-(2,3-环硫代丙基)硫化物的合成(pH10.0)
向10升反应容器添加二(3-氯-2-羟丙基)硫化物(1072.48g)、甲苯(toluene)1300g、甲醇800g,进行搅拌,把反应温度调到25℃。到达25℃时,滴加NaOH(50%aq.,783.08g),滴加时的反应温度维持在37℃,进行反应。滴加进行在1小时以内,之后在37℃条件下放置约30分钟发酵,发酵结束后,添加甲苯2000g,约搅拌30分钟,进行分层,以1g盐酸溶液中和上清液有机溶液,最大限度去除水分,向有几层有机溶液再次添加甲醇400g、进行搅拌,在反应温度8℃下添加硫脲素(thiourea)(1117.65g)及无水醋酸(70g),把反应温度调高到16.5℃,反应24小时。反应结束点通过HPLC确认,出发物质小时,生成物没有进一步变化为准。反应结束后,停止搅拌,以水清洗3次通过层分离获得的有几层,向获得的有几层添加0.1%氨水,去除有机溶剂,获得pH为10.0的二-(2,3-环硫代丙基)硫化物。测得屈光率(nD,20℃)为1.614。
实施例1
向合成例5获得的pH为7.0的二-(2,3-环硫代丙基)硫化物100g,添加内部脱模剂8-PENPP0.01g、紫外线吸收剂HOPBT1.0g、聚合引发剂TBPB0.4g、有机颜料HTAQ(20ppm)及PRD(10ppm),在20℃进行搅拌混合,获得了均匀溶液。对该混合溶液,以400Pa条件,进行1小时脱泡。之后,通过1μm PTFE制过滤器进行过滤,注入到由玻璃模板和胶带构成的模具中。把该模具放入聚合烤箱中,在30℃条件下8小时,以30~100℃温度,经15小时慢慢升温,进行聚合。聚合结束后,从烤箱取出模具。模具的脱模性呈现良好。对获得的树脂在110℃下进行2小时退火处理。获得的物性为屈光率(nE)1.702,阿贝数34.5,耐热性(Tg)95℃。对注入模具的溶液状态通过肉眼做了观察,脱模后确认了异物、未发现异常,未出现白化及脉理。
实施例2~3
以与实施例1相同的方法,按表1记载的各种配比分别制造各合成物及晶片后,把其评价结果记录在表1。
比较例1
向合成例2获得的pH为2.5的二-(2,3-环硫代丙基)硫化物100g,添加内部脱模剂8-PENPP0.01g、紫外线吸收剂HOPBT1.0g、聚合引发剂TBPB0.4g、有机颜料HTAQ(20ppm)及PRD(10ppm),在20℃进行搅拌混合,获得了均匀溶液。对该混合溶液,以400Pa条件,进行1小时脱泡。之后,通过1μm PTFE制过滤器进行过滤,注入到由玻璃模板和胶带构成的模具中。把该模具放入聚合烤箱中,在30℃条件下8小时,以30~100℃温度,经15小时慢慢升温,进行聚合。但树脂合成物未发生硬化,而是颜色变黄。
比较例2~3
以与比较例1相同的方法,硬化树脂合成物,把获得的资料记录在表1。
[略称]
EPS:二(2,3-环硫代丙基)硫化物(bis(2,3-epithiopropyl)sulfide)
8-PENPP:聚氧化乙烯壬基苯酚醚磷酸酯(polyoxyethylenenonylphenoletherphosphate)
HOPBT:2-(2'-羟基-5'-t-辛基苯基)-2H-苯并三唑(2-(2'-hydroxy-5'-t-octylphenyl)-2H-benzotriazole)
TBPB:四丁基溴化磷(tetrabutylphosphonium bromide)
HTQA:1-羟基-4-(p-甲苯胺)-蒽醌(1-hydroxy-4-(p-toluidine)anthraquinone
PRD:芘酮染料(perinone dye)
产业利用可行性
本发明可以避免未硬化和聚合不均匀,容易制造品质优良的硫代环氧基系光学材料。本发明制造的硫代环氧基系光学材料可以代替现有光学材料,广泛应用于各种领域。具体地,可用于塑料眼镜镜片,眼镜镜片上安装偏光膜制造的3D偏光镜片,相机镜片等,除此之外还可以利用于三棱镜、光纤维、光盘等记录媒介基板或着色过滤器和紫外线吸收过滤器等多种光学产品。
Claims (7)
1.一种硫代环氧基系光学材料制造方法,其特征在于:包括
合成反应结束后,对含硫代环氧基化合物的有机层进行层分离,进行清洗后,添加硫酸或氨水、去除有机溶剂,获得pH值4~8的硫代环氧基化合物的阶段;
制造含所述pH值4~8的硫代环氧基化合物的聚合性合成物的阶段;
对所述聚合性合成物进行注模聚合的阶段。
2.根据权利要求1所述的硫代环氧基系光学材料制造方法,其特征在于:
所述硫代环氧基化合物是选自二-(2,3-环硫代丙基)硫化物(bis-(2,3-epithiopropyl)sulfide)、二-(2,3-环硫代丙基)二硫化物(bis-(2,3-epithiopropyl)disulfide)、1,3-及1,4-二(β-环硫代丙基硫代)环己烷)、1,3-及1,4-二(β-环硫代丙基硫代甲基)环己烷)、2,5-二(β-环硫代丙基硫代甲基)-1,4-二噻烷、2,5-二(β-环硫代丙基硫代乙基硫代甲基)-1,4-二噻烷、2-(2-β-环硫代丙基硫代乙基硫代)-1,3-二(β-环硫代丙基硫代)丙烷的1种或2种以上化合物。
3.根据权利要求1所述的硫代环氧基系光学材料制造方法,其特征在于:
所述聚合性合成物还包括聚硫醇化合物。
4.根据权利要求3所述的硫代环氧基系光学材料制造方法,其特征在于:
所述聚合性合成物还包括聚异氰酸酯化合物。
5.根据权利要求1至4中的某一项所述的硫代环氧基系光学材料制造方法,其特征在于:
所述聚合性合成物作为反应性树脂改性剂还包括烯烃化合物。
6.根据权利要求1至4中的某一项所述的硫代环氧基系光学材料制造方法,其特征在于:
所述聚合性合成物作为内部脱模剂还包括磷酸酯化合物。
7.根据权利要求6所述的硫代环氧基系光学材料制造方法,其特征在于:
所述磷酸酯化合物是选自:聚氧化乙烯壬基苯酚醚磷酸酯,其中添加环氧乙烷5摩尔的5重量%、添加4摩尔的80重量%、添加3摩尔的10重量%、添加1摩尔的5重量%;聚氧化乙烯壬基苯酚醚磷酸酯,其中添加环氧乙烷9摩尔的3重量%、添加8摩尔的80重量%、添加9摩尔的5重量%、添加7摩尔的6重量%、添加6摩尔的6重量%;聚氧化乙烯壬基苯酚醚磷酸酯,其中添加环氧乙烷13摩尔的3重量%、添加12摩尔的80重量%、添加11摩尔的8重量%、添加9摩尔的3重量%、添加4摩尔的6重量%;聚氧化乙烯壬基苯酚醚磷酸酯,其中添加环氧乙烷17摩尔的3重量%、添加16摩尔的79重量%、添加15摩尔的10重量%、添加14摩尔的4重量%、添加13摩尔的4重量%;聚氧化乙烯壬基苯酚醚磷酸酯,其中添加环氧乙烷21摩尔的5重量%、添加20摩尔的76重量%、添加19摩尔的7重量%、添加18摩尔的6重量%、添加17摩尔的4重量%;及Zelec UNTM的1种或2种以上化合物。
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