CN104053657B - 硫代环氧基系光学材料的制造方法及其聚合性合成物 - Google Patents
硫代环氧基系光学材料的制造方法及其聚合性合成物 Download PDFInfo
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- CN104053657B CN104053657B CN201380005670.6A CN201380005670A CN104053657B CN 104053657 B CN104053657 B CN 104053657B CN 201380005670 A CN201380005670 A CN 201380005670A CN 104053657 B CN104053657 B CN 104053657B
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- 125000005068 thioepoxy group Chemical group S(O*)* 0.000 title claims abstract description 46
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- 238000006116 polymerization reaction Methods 0.000 claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims description 53
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- 229910019142 PO4 Inorganic materials 0.000 claims description 30
- 239000010452 phosphate Substances 0.000 claims description 30
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- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 20
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 19
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
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- 238000005987 sulfurization reaction Methods 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 229940096522 trimethylolpropane triacrylate Drugs 0.000 description 1
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- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
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- 238000004383 yellowing Methods 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
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Abstract
本发明涉及硫代环氧基系光学材料制造方法和其聚合性合成物,及用于此的硫代环氧基化合物。本发明提供一种光学材料用硫代环氧基化合物和包括其的聚合性合成物及聚合此的光学材料制造方法,以4~15重量%含2,3‑环氧丙基(2,3‑环氧硫代丙基)硫化物化合物及/或2,3‑环氧丙基(2,3‑环氧硫代丙基)二硫化物化合物。本发明解决硫代环氧基系光学材料的色相不稳定,脱模、聚合不均匀方面的问题。
Description
技术领域
本发明涉及硫代环氧基系光学材料,尤其涉及最大限度解决色相不稳定等问题的清澈透明硫代环氧基系光学材料制造方法和其聚合性合成物,及用于此的硫代环氧基化合物。
背景技术
与现有技术的玻璃镜片相比,塑料镜片重量轻、耐冲击性能强、着色容易,最近大部分眼睛镜片都适用塑料镜片。其中,具有代表性的有二乙烯乙二醇二烯丙基碳酸酯(diethylene glycol bisallyl carbonate)(CR-39)镜片,适用于普通镜片。这种镜片色像差(chromatic aberration)小,给人提供舒适的视野,但屈光率低,很难满足高屈光率要求。韩国专利公告公报1993-0006918号及1992-0005708号等公开一种让聚硫醇化合物与聚异氰酸酯化合物反应得到的硫乌拉坦系镜片。而韩国注册专利10-0681218号公开了一种硫代环氧基系塑料镜片。
现有技术中,硫乌拉坦镜片虽然屈光率高,冲击强度优秀,但存在镜片表面硬度差,中心凹陷等问题,而且存在屈光率变高时阿贝数急剧下降的问题。硫代环氧基系镜片虽然屈光率高,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。为了解决这种问题,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。
但作为主要单体成分含硫代环氧基化合物的硫代环氧基系镜片仍然存在色相不稳定的问题。韩国公开专利10-0681218号查明硫代环氧基化合物制造过程中,环氧基化合物转变为硫代环氧基化合物的过程中的纯度,即转换过程中由于副反应产生的不纯物硫代环氧基化合物的含量是影响镜片色相的原因,公开了一种降低这种不纯物硫代环氧基化合物含量后得到的聚合性合成物及降低所述含量的方法。
发明内容
发明的课题
本发明诣在解决作为主要单体成分含硫代环氧基化合物的硫代环氧基系镜片出现的色相不稳定问题,其目的在于:提供一种无色相、脱模、聚合不均匀等方面问题,清澈透明的高品质硫代环氧基系光学材料制造方法和其聚合性合成物,及用于其的硫代环氧基化合物。
本发明的各发明人偶然发现制造硫代环氧基化合物的过程中,从环氧基转变成硫代环氧基时,未完全转变为硫代环氧基,而是同时具有2,3-环氧丙基及2,3-环氧硫代丙基的中间化合物2,3-环氧丙基(2,3-环氧硫代丙基)硫化物化合物及/或2,3-环氧丙基(2,3-环氧硫代丙基)二硫化物化合物以4~15重量%含量存在于硫代环氧基化合物中时,与含量小于4重量%或超出15重量%的情况相比,硫代环氧基化合物的色相优秀,而以此制造的光学材料不会发生变黄问题,色相好,没有脱模、聚合不均匀方面的问题。本发明是据此完成的。
实施方案
本发明提供了:
一种硫代环氧基系聚合性合成物,其含硫代环氧基化合物(A)和制造所述硫代环氧基化合物(A)的过程中以副产物形式生成的化合物(B),其特征在于:所述以副产物形式生成的化合物(B)为以下式1表示的2,3-环氧丙基(2,3-环氧硫代丙基)硫化物化合物,2,3-环氧丙基(2,3-环氧硫代丙基)二硫化物化合物中的某一种以上,以4~15重量%含于所述聚合性合成物中。本发明的聚合性合成物还可以包括聚异氰酸酯化合物及/或聚硫醇化合物。所述聚合性合成物还可以包括作为反应性树脂改性剂的烯烃化合物。另外,所述聚合性合成物还可以包括内部脱模剂。
【式1】
另外,本发明提供了:
一种硫代环氧基系光学材料的制造方法,其聚合所述聚合性合成物。
另外,本发明提供了:
一种通过聚合所述聚合性合成物得到的硫代环氧基系光学材料和一种由该光学材料构成的镜片。
发明效果
本发明中,从环氧基转变成硫代环氧基时产生的中间化合物——2,3-环氧丙基及2,3-环氧硫代丙基的中间化合物2,3-环氧丙基(2,3-环氧硫代丙基)硫化物化合物及/或2,3-环氧丙基(2,3-环氧硫代丙基)二硫化物化合物以4~15重量%含量残存于所制造的硫代环氧基化合物中,可以解决硫代环氧基系光学材料的色相不稳定、脱模、聚合不均匀方面的问题。本发明可以以很高收率容易获得清澈透明的高品质镜片,通过本发明获得的硫代环氧基系光学材料可以用于矫正用镜片,墨镜镜片、时尚镜片、变色镜片、相机镜片、光学装置镜片等。
具体实施方式
本发明中,用于聚合硫代环氧基系光学材料的硫代环氧基化合物(A)以4~15重量%含制造过程中以副产物形式生成的下式1表示的2,3-环氧丙基(2,3-环氧硫代丙基)硫化物化合物及/或2,3-环氧丙基(2,3-环氧硫代丙基)二硫化物化合物中的某一种以上。2,3-环氧丙基(2,3-环氧硫代丙基)硫化物化合物和2,3-环氧丙基(2,3-环氧硫代丙基)二硫化物化合物是从环氧基转变成硫代环氧基时产生的中间化合物,该中间化合物在包含于聚合性合成物的硫代环氧基化合物中的含量为4~15重量%时,与含量小于4重量%或超出15重量%的情况相比,所聚合出来的光学材料色相好,没有脱模、聚合不均匀方面的问题。
【式1】
所述硫代环氧基化合物比如可以是二(2,3-环硫代丙基硫)硫化物(bis(2,3-epithiopropyl)sulfide)、二(2,3-环硫代丙基硫)二硫化物(bis(2,3-epithiopropyl)disulfide)、2,3-环二硫代丙基硫(2,3-环硫代丙基硫)二硫化物(2,3-epidithiopropyl(2,3-epithiopropyl)disulfide)、2,3-环二硫代丙基硫(2,3-环硫代丙基硫)硫化物(2,3-epidithiopropyl(2,3-epithiopropyl)sulfide)、1,3及1,4-二(β-环硫代丙基硫代)环己烷)(bis(β-epithiopropylthio)cyclohexane)、1,3及1,4-二(β-环硫代丙基硫代甲基)环己烷)(bis(β-epithiopropylthiomethyl)cyclohexane)、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]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)等具有脂肪族骨骼的环硫化物(episulfide)化合物。除此之外,作为硫代环氧基化合物,还可以使用带环硫化(episulfide)基的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)、2,3-环二硫代丙基硫(2,3-环硫代丙基硫)硫化物、2,3-环二硫代丙基硫(2,3-环硫代丙基硫)二硫化物、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。
本发明的聚合性合成物所含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,使用1种以上2,2-二甲基戊烷二异氰酸酯(2,2-dimethyl pentanediisocyanate)、六亚甲基二异氰酸酯(hexa methylene diisocyanate)、2,2,4-三甲基己烷二异氰酸酯(2,2,4-trimethyl hexane diisocyanate)、丁烯二异氰酸酯(butenediisocyanate)、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 methylene triisocyanate)、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(isophorone diisocyanate)、1,2-二(异氰酸基甲基)环己烷(1,2-bis(isocyanatomethyl)cyclo hexane)、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)cyclohexane)、二环己基甲烷二异氰酸酯(dicyclo hexyl methane diisocyanate)、环己烷二异氰酸酯(cyclo hexane diisocyanate)、甲基环己烷二异氰酸酯(methyl cyclohexane diisocyanate)、二环己基二甲基甲烷异氰酸酯(dicyclo hexyl dimethylmethane isocyanate)、2,2-二甲基二环己基甲烷异氰酸酯(2,2-dimethyl dicyclo hexylmethane isocyanate)等脂环族异氰酸酯化合物(Cycloaliphatic isocyanatecompounds);亚二甲苯基二异氰酸酯(xylylene diisocyanate(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(isocyanato butyl)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(isocyanatomethyl)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(isopropylphenylene diisocyanate)、二甲基亚苯基二异氰酸酯(dimethyl phenylenediisocyanate)、二乙基亚苯基二异氰酸酯(diethyl phenylene diisocyanate)、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(benzene triisocyanate)、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 methane diisocyanate)、3,3-二甲基二苯基甲烷-4,4-二异氰酸酯(3,3-dimethyl diphenyl methane-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(hexa hydrobenzene diisocyanate)、六氢二苯基甲烷-4,4-二异氰酸酯(hexa hydro diphenyl methane-4,4-diisocyanate)等芳香族异氰酸酯化合物(aromatic isocyanate compounds);二(异氰酸基乙基)硫化物(bis(isocyanatoethyl)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)磺(bis(isocyanato methyl)sulfone)、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(isocyanato ethyl 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 methylthio)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-thia pentane)等含硫脂肪族异氰酸酯化合物(sulfur aliphaticisocyanate 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-isocyanatomethyl 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 diphenyl disulphide-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 diphenyldisulphide-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-dimethoxy diphenyl disulphide-3,3-diisocyanate)等含硫芳香族异氰酸酯化合物(sulfur aromatic isocyanate compounds);2,5-二异氰酸基噻吩(2,5-diisocyanato thiophene)、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)。之外,只要是具有至少1个以上异氰酸及/或异硫代氰酸基化合物,可以使用1种或2种以上,还可以使用这些异氰酸酯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(IPDI)、六亚甲基二异氰酸酯(HDI)、环己烷二异氰酸酯(H12MDI)、亚二甲苯基二异氰酸酯、3,8-二(异氰酸甲基)三环[5,2,1,02,6]癸烷(3,8-bis(isocyanatemethyl)tricyclo[5,2,1,02,6]decane)、3,9-二(异氰酸甲基)三环[5,2,1,02,6]癸烷(3,9-bis(isocyanatemethyl)tri cyclo[5,2,1,02,6]decane)、4,8-二(异氰酸甲基)三环[5,2,1,02,6]癸烷(4,8-bis(isocyanatemethyl)tricyclo[5,2,1,02,6]decane)、2,5-二(异氰酸甲基)二环[2,2,1]庚烷(2,5-bis(isocyanatemethyl)bicyclo[2,2,1]heptane)、2,6-二(异氰酸甲基)二环[2,2,1]庚烷(2,6-bis(isocyanatemethyl)bicyclo[2,2,1]heptane)中的1种以上。
本发明聚合性合成物所含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-dithiaoctane)、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)、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)propyl thio)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-mercapto propane)、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-mercapto ethyl 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 ethylthio)-3-mercapto propyl)sulfide)、二(2-(2-巯基乙基硫代)-3-巯基丙基)二硫化物(bis(2-(2-mercapto ethyl thio)-3-mercapto propyl)disulfide)、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 thi)-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(mercaptomethy)-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)thi)propane-1-thiol)、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 thiaheptadecane-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 thiaoctadecane-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 erythritol Tetrakis(3-mercapto propionate))、三亚甲醇丙烷三(3-巯基丙酸酯)(trimethylol propane tris(3-mercapto propionate))、季戊四醇四(2-巯基醋酸盐)(Pentaerythritol Tetrakis(2-mercapto acetate))、二季戊四醇-乙醚-苯丙锡(3-巯基丙酸酯)(bispenta erythritol-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。
本发明的聚合性合成物可以包括内部脱模剂,内部脱模剂最好是包括酸性磷酸酯化合物。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。本发明合成物作为内部脱模剂,最好是使用从4-PENPP[聚氧化乙烯壬基苯酚醚磷酸酯(poly oxy ethylene nonyl phenol ether phosphate)(5重量%的5摩尔环氧乙烷加合物,80重量%的4摩尔加合物,10重量%的3摩尔加合物,5重量%的1摩尔加合物)],8-PENPP[聚氧化乙烯壬基苯酚醚磷酸酯(3重量%的9摩尔环氧乙烷加合物,80重量%的8摩尔加合物,5重量%的9摩尔加合物,6重量%的7摩尔加合物,6重量%的6摩尔加合物)],12-PENPP[聚氧化乙烯壬基苯酚醚磷酸酯(3重量%的13摩尔环氧乙烷加合物,80重量%的12摩尔加合物,8重量%的11摩尔加合物,3重量%的9摩尔加合物,6重量%的4摩尔加合物)],16-PENPP[聚氧化乙烯壬基苯酚醚磷酸酯(3重量%的17摩尔环氧乙烷加合物,79重量%的16摩尔加合物,10重量%的15摩尔加合物,4重量%的14摩尔加合物,4重量%的13摩尔加合物)],20-PENPP[聚氧化乙烯壬基苯酚醚磷酸酯(5重量%的21摩尔环氧乙烷加合物,76重量%的20摩尔加合物,7重量%的19摩尔加合物,6重量%的18摩尔加合物,4重量%的17摩尔加合物)],4-PPNPP[聚氧化丙烯壬基苯酚醚磷酸酯(poly oxypropylene nonyl phenol ether phosphate)(5重量%的5摩尔环氧丙烷加合物,80重量%的4摩尔加合物,10重量%的3摩尔加合物,5重量%的1摩尔加合物)],8-PPNPP[聚氧化丙烯壬基苯酚醚磷酸酯(3重量%的9摩尔环氧丙烷加合物,80重量%的8摩尔加合物,5重量%的9摩尔加合物,6重量%的7摩尔加合物,6重量%的6摩尔加合物)],12-PPNPP[聚氧化丙烯壬基苯酚醚磷酸酯(3重量%的13摩尔环氧丙烷加合物,80重量%的12摩尔加合物,8重量%的11摩尔加合物,3重量%的9摩尔加合物,6重量%的4摩尔加合物)],16-PPNPP[聚氧化丙烯壬基苯酚醚磷酸酯(3重量%的17摩尔环氧丙烷加合物,79重量%的16摩尔加合物,10重量%的15摩尔加合物,4重量%的14摩尔加合物,4重量%的13摩尔加合物)],20-PPNPP[聚氧化丙烯壬基苯酚醚磷酸酯(5重量%的21摩尔环氧丙烷加合物,76重量%的20摩尔加合物,7重量%的19摩尔加合物,6重量%的18摩尔加合物,4重量%的17摩尔加合物)],ZelecUNTM中选择的一种以上磷酸酯化合物。在同等目的下,也可以使用这种磷酸酯化合物的卤族取代物及各种其他取代物。
本发明的聚合性合成物为了提高共聚物光学树脂(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 hexyl acrylate)、环己基甲基丙烯酸脂(cyclo hexylmethacrylate)、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 methyl methacrylate)、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(phenoxyethylacrylate)、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(m-二环氧乙烷)(3,9-divinyl Spiro bi(m-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。
本发明的光学材料通过注模聚合获。即,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。这里,根据塑料镜片的要求物性,可按需要进行减压脱泡或加压、减压等过滤处理。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。
通过硬化得到的硫代环氧基化合物和异氰酸酯化合物及硫醇化合物共聚体,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℃。
本发明的合成物最好是添加磷酸酯化合物注模聚合。磷酸酯化合物的说明同上。除此之外,本发明的聚合性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。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 withdrawing group)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以有所不同。
本发明的共聚物树脂,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,适合于应用在眼镜镜片、相机镜片、发光二极管等光学材料,光学元件。
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。
【实施例】
本发明的实施例只是为了具体说明本发明而提出的,本发明的权利要求不受限于这些实施例。
试验及评价方法
色相:YI值利用SHIMADZU公司Model UV-2450上安装IRS-2200集光装置的色分析装置检测,检测方法为把空气作为基准,固定在固定镜片的装置,检测了色相YI值。色相评价中YI的值意味着黄色指数,是可以通过色彩色差计检测的值,YI值越低色相越良好。对实施例1中得到的树脂检测YI值后,如果与之相比存在+1以上的差异,则记录为“X”,不足时记录为“O”。
屈光率,阿贝数:使用了Atago公司的IT及DR-M4型号阿贝屈光计,在20℃下检测。
【合成例1】二(3-氯-2-羟丙基)硫化物(bis(3-chloro-2-hydroxylpropyl)sulfide)(BCPS)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。如果存在3-氯-2-羟基-丙基-1-硫醇,则以含量计算GC相对积分比,添加表氯醇,合成了二(3-氯-2-羟丙基)硫化物(BCPS)。
【合成例2】二(3-氯-2-羟丙基)二硫化物(bis(3-chloro-2-hydroxylpropyl)disulfide)(BCPDS)的合成
向10升反应器添加表氯醇(epichlorohydrin)(5563g,60.12mol)及甲醇(5000g)后,把反应温度调节为5℃,当反应温度到达5℃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3-氯-2-羟基-丙基-1-硫醇。通过GC确认最终生成物,当表氯醇完全消失,生成3-氯-2-羟基-丙基-1-硫醇化合物时,结束了反应。3-氯-2-羟基-丙基-1-硫醇通过减压蒸馏获得了6550g。把3-氯-2-羟基-丙基-1-硫醇(1500g,11.85mol)及甲醇1500g放入反应器中,把温度降到10℃,慢慢滴加35%过氧化氢(575.61g,5.92mol),合成了二(3-氯-2-羟丙基)二硫化物(BCPDS)。
【合成例3】二(2,3环硫代丙基)硫化物的合成(BEPS-1)
向10升反应容器添加二(3-氯-2-羟丙基)硫化物(1072.48g,8.47mol)、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,出发物质几乎消失,2,3-环氧基丙基(2,3环硫代丙基)硫化物化合物在GC分析中的含量为6%时结束反应,停止搅拌,以水清洗3次通过层分离获得的有机层,去除有机溶剂,获得二-(2,3-环硫代丙基)硫化物。测得屈光率(nD,20℃)为1.618。
【合成例4】二(2,3环硫代丙基)硫化物的合成(BEPS-2)
向10升反应容器添加二(3-氯-2-羟丙基)硫化物(1072.48g,8.47mol)、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,出发物质几乎消失,2,3-环氧基丙基(2,3环硫代丙基)硫化物化合物在GC分析中的含量为9%时结束反应,停止搅拌,以水清洗3次通过层分离获得的有机层,去除有机溶剂,获得二-(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(BEPS-3)
向10升反应容器添加二(3-氯-2-羟丙基)硫化物(1072.48g,8.47mol)、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,出发物质几乎消失,2,3-环氧基丙基(2,3环硫代丙基)硫化物化合物在GC分析中的含量为14%时结束反应,停止搅拌,以水清洗3次通过层分离获得的有机层,去除有机溶剂,获得二-(2,3-环硫代丙基)硫化物。测得屈光率(nD,20℃)为1.611。
【合成例6】二(2,3环硫代丙基)二硫化物的合成(BEPDS)
向10升反应容器添加二(3-氯-2-羟丙基)二硫化物(1229.34g,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,出发物质几乎消失,2,3-环氧基丙基(2,3环硫代丙基)二硫化物化合物在GC分析中的含量为10%时结束反应,停止搅拌,以水清洗3次通过层分离获得的有机层,去除有机溶剂,获得二-(2,3-环硫代丙基)二硫化物(BEPDS)。测得屈光率(nD,20℃)为1.631。
【合成比较例1】二(2,3环硫代丙基)硫化物的合成(BEPS-4)
向10升反应容器添加二(3-氯-2-羟丙基)硫化物(1072.48g,8.47mol)、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,出发物质几乎消失,2,3-环氧基丙基(2,3环硫代丙基)硫化物化合物在GC分析中的含量为3.5%时结束反应,停止搅拌,以水清洗3次通过层分离获得的有机层,去除有机溶剂,获得二-(2,3-环硫代丙基)硫化物。测得屈光率(nD,20℃)为1.623。
【合成比较例2】二(2,3环硫代丙基)硫化物的合成(BEPS-5)
向10升反应容器添加二(3-氯-2-羟丙基)硫化物(1072.48g,8.47mol)、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,出发物质几乎消失,2,3-环氧基丙基(2,3环硫代丙基)硫化物化合物在GC分析中的含量为16%时结束反应,停止搅拌,以水清洗3次通过层分离获得的有机层,去除有机溶剂,获得二-(2,3-环硫代丙基)硫化物。测得屈光率(nD,20℃)为1.607。
【实施例1】
硫代环氧基化合物使用了合成例3合成的二(2,3环硫代丙基)硫化物(BEPS-1)89g,异氰酸酯化合物使用了异佛尔酮二异氰酸酯5g,硫醇化合物使用了二(2-巯基乙基)硫化物6g,内部脱模剂使用了磷酸酯8-PENPP[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%)]0.15g,四丁基溴化鏻(Tetrabutyl phosphonium Bromide)0.2g,三苯基膦(Triphenylphosphine)0.1g,有机染料HTAQ(20ppm)及PRD(10ppm),紫外线吸收剂HOPBT1.5,在20℃条件下混合溶解,得到了均匀溶液。对该混合溶液,在400Pa条件下,脱泡1小时。之后以1μm PTFE过滤器进行过滤,注入了由玻璃和胶带构成的模具中。把模具投放到聚合烤箱中,从25℃~130℃止,经21小时慢慢升温。聚合结束后从烤箱取出模具。模具的脱模性良好。在130℃条件下,对获得的树脂进行了4小时退火处理。获得的树脂物性为屈光率(nE)1.699,阿贝数为35。注入模具前,肉眼观察了溶解后的状态,脱模后确认表面不良,结果没有异常,看不见白化,YI值为1.61,获得了质量稳定的树脂。
【实施例2~4】
除了适用表1记载的配方,以与实施例1相同的方法分别制造了各合成物及光学镜片,做了评价。结果如下表1所示。
【比较例2~4】
除了适用表1记载的配方,以与实施例1相同的方法分别制造了各合成物及光学镜片,做了评价。结果如下表1所示。
【表1】
[略称]
单体
BEPS:二(2,3-环硫代丙基)硫化物(bis(2,3-epithiopropyl)sulfide)
BEPDS:二(2,3-环硫代丙基)二硫化物(bis(2,3-epithiopropyl)sulfide)
BMES:二-(2,3-环硫代丙基)硫化物(bis-(2,3-epithiopropyl)sulfide)
IPDI:异佛尔酮二异氰酸酯(isophorondiisocyanate)
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:四丁基溴化鏻(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)
Claims (15)
1.一种硫代环氧基系聚合性合成物,其含硫代环氧基化合物(A)和制造所述硫代环氧基化合物(A)的过程中以副产物形式生成的化合物(B),其特征在于:
所述硫代环氧基化合物(A)是选自二-(2,3-环硫代丙基)硫化物、二-(2,3-环硫代丙基)二硫化物、1,3-二(β-环硫代丙基硫代)环己烷、1,4-二(β-环硫代丙基硫代)环己烷、1,3-二(β-环硫代丙基硫代甲基)环己烷、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种以上物质;
所述以副产物形式生成的化合物(B)为以下式1表示的2,3-环氧丙基(2,3-环氧硫代丙基)硫化物化合物,2,3-环氧丙基(2,3-环氧硫代丙基)二硫化物化合物中的一种以上,以4~15重量%含于所述聚合性合成物中,
【式1】
式1中,X为S或S-S。
2.根据权利要求1所述的硫代环氧基系聚合性合成物,其特征在于:
还包含作为聚合性催化剂的鏻盐类。
3.根据权利要求1所述的硫代环氧基系聚合性合成物,其特征在于:
还包括聚异氰酸酯化合物。
4.根据权利要求1所述的硫代环氧基系聚合性合成物,其特征在于:
还包括聚硫醇化合物。
5.根据权利要求1所述的硫代环氧基系聚合性合成物,其特征在于:
还包括聚异氰酸酯化合物、聚硫醇化合物及作为聚合性催化剂的鏻盐类。
6.根据权利要求3或5所述的硫代环氧基系聚合性合成物,其特征在于:
所述聚异氰酸酯化合物是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、亚二甲苯基二异氰酸酯、3,8-二(异氰酸甲基)三环[5,2,1,02,6]癸烷、3,9-二(异氰酸甲基)三环[5,2,1,02,6]癸烷、4,8-二(异氰酸甲基)三环[5,2,1,02,6]癸烷、2,5-二(异氰酸甲基)二环[2,2,1]庚烷、2,6-二(异氰酸甲基)二环[2,2,1]庚烷的1种以上物质。
7.根据权利要求4或5所述的硫代环氧基系聚合性合成物,其特征在于:
所述聚硫醇化合物是二(2-巯基乙基)硫化物。
8.根据权利要求1或5所述的硫代环氧基系聚合性合成物,其特征在于:
还包括作为反应性树脂改性剂的烯烃化合物。
9.根据权利要求1至5中任一项所述的硫代环氧基系聚合性合成物,其特征在于:
还包括作为内部脱模剂的选自:4-PENPP,即聚氧化乙烯壬基苯酚醚磷酸酯,其由5重量%的5摩尔环氧乙烷加合物,80重量%的4摩尔加合物,10重量%的3摩尔加合物,5重量%的1摩尔加合物构成;12-PENPP,即聚氧化乙烯壬基苯酚醚磷酸酯,其由3重量%的13摩尔环氧乙烷加合物,80重量%的12摩尔加合物,8重量%的11摩尔加合物,3重量%的9摩尔加合物,6重量%的4摩尔加合物构成;16-PENPP,即聚氧化乙烯壬基苯酚醚磷酸酯,其由3重量%的17摩尔环氧乙烷加合物,79重量%的16摩尔加合物,10重量%的15摩尔加合物,4重量%的14摩尔加合物,4重量%的13摩尔加合物构成;4-PPNPP,即聚氧化丙烯壬基苯酚醚磷酸酯,其由5重量%的5摩尔环氧丙烷加合物,80重量%的4摩尔加合物,10重量%的3摩尔加合物,5重量%的1摩尔加合物构成;12-PPNPP,即聚氧化丙烯壬基苯酚醚磷酸酯,其由3重量%的13摩尔环氧丙烷加合物,80重量%的12摩尔加合物,8重量%的11摩尔加合物,3重量%的9摩尔加合物,6重量%的4摩尔加合物构成;16-PPNPP,即聚氧化丙烯壬基苯酚醚磷酸酯,其由3重量%的17摩尔环氧丙烷加合物,79重量%的16摩尔加合物,10重量%的15摩尔加合物,4重量%的14摩尔加合物,4重量%的13摩尔加合物构成;和Zelec UNTM的1种以上磷酸酯化合物。
10.一种硫代环氧基系光学材料制造方法,其特征在于:
聚合权利要求1至5中任一项的聚合性合成物。
11.根据权利要求10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含作为聚合性催化剂的鏻盐类。
12.根据权利要求10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含作为聚硫醇化合物的二(2-巯基乙基)硫化物。
13.根据权利要求10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作为内部脱模剂的选自:4-PENPP,即聚氧化乙烯壬基苯酚醚磷酸酯,其由5重量%的5摩尔环氧乙烷加合物,80重量%的4摩尔加合物,10重量%的3摩尔加合物,5重量%的1摩尔加合物构成;12-PENPP,即聚氧化乙烯壬基苯酚醚磷酸酯,其由3重量%的13摩尔环氧乙烷加合物,80重量%的12摩尔加合物,8重量%的11摩尔加合物,3重量%的9摩尔加合物,6重量%的4摩尔加合物构成;16-PENPP,即聚氧化乙烯壬基苯酚醚磷酸酯,其由3重量%的17摩尔环氧乙烷加合物,79重量%的16摩尔加合物,10重量%的15摩尔加合物,4重量%的14摩尔加合物,4重量%的13摩尔加合物构成;4-PPNPP,即聚氧化丙烯壬基苯酚醚磷酸酯,其由5重量%的5摩尔环氧丙烷加合物,80重量%的4摩尔加合物,10重量%的3摩尔加合物,5重量%的1摩尔加合物构成;12-PPNPP,即聚氧化丙烯壬基苯酚醚磷酸酯,其由3重量%的13摩尔环氧丙烷加合物,80重量%的12摩尔加合物,8重量%的11摩尔加合物,3重量%的9摩尔加合物,6重量%的4摩尔加合物构成;16-PPNPP,即聚氧化丙烯壬基苯酚醚磷酸酯,其由3重量%的17摩尔环氧丙烷加合物,79重量%的16摩尔加合物,10重量%的15摩尔加合物,4重量%的14摩尔加合物,4重量%的13摩尔加合物构成;和ZelecUNTM的1种以上磷酸酯化合物。
14.一种硫代环氧基系光学材料,其特征在于:
聚合权利要求1至5中任一项的聚合性合成物得到。
15.一种光学镜片,其特征在于:
由权利要求14的光学材料构成。
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