TWI696892B - 在全像光聚合物配製物中作為寫入單體之芳香族二醇醚 - Google Patents
在全像光聚合物配製物中作為寫入單體之芳香族二醇醚 Download PDFInfo
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- TWI696892B TWI696892B TW104112982A TW104112982A TWI696892B TW I696892 B TWI696892 B TW I696892B TW 104112982 A TW104112982 A TW 104112982A TW 104112982 A TW104112982 A TW 104112982A TW I696892 B TWI696892 B TW I696892B
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Abstract
本發明關於一種光聚合物配製物,其包含特定芳香族二醇醚作為寫入單體、基質聚合物(matrix polymers)及光起始劑。本發明進一步提供一種可使用本發明光聚合物配製物獲得之未曝光的全像介質,及一種曝光的全像介質,其可藉由使一全像圖曝光至本發明未曝光的全像介質內而獲得。本發明同樣提供一種包含本發明曝光的全像介質之視覺顯示器(visual display),亦提供本發明曝光的全像介質的用途,以用於晶片卡、身分證件、3D影像、產品保護標籤、標籤、鈔票或全像光學元件之製造,及一種特定芳香族二醇醚。
Description
本發明關於一種光聚合物配製物,其包含寫入單體、基質聚合物及光起始劑。本發明進一步提供一種可使用本發明光聚合物配製物獲得之未曝光的全像介質,及一種可藉使一全像圖曝光至本發明未曝光的全像介質內獲得之曝光的全像介質。本發明同樣提供一種視覺顯示器,其包含本發明曝光的全像介質,係使用本發明曝光的全像介質用於晶片卡、身分證件、3D影像、產品保護標籤、標籤、鈔票或全像光學元件之製造,及一種特定芳香族二醇醚。
對於光聚合物配製物之用途,重要作用由在該光聚合物中藉全像曝光所產生的折射率對比度△n所產生。在全像曝光中,訊號光束與參考光束之干涉場(在最簡單情況中二個平面波之干涉場)藉,例如,在干涉場中高強度的位點(loci)之高折射性丙烯酸酯類之局部光聚合反應而被映圖至一折射率光柵(refractive index grating)內。在該光聚合物(該全像圖)中的折射率光柵含有訊號光束之全部資訊。藉只利用參考光束照明全像圖,該訊號之後可被重建(reconstructed)。由此重建的訊號強度相對於入射參考光的強度在下文中被稱為繞射效率(dirrraction efficiency,DE)。
在最簡單的產生自二個平面波的疊置作用(superposition)之全像圖情況中,該DE為在重建上繞射的光強度對該入射參考光與繞射光的強度總和之比例。該DE越高,相關於欲可視化該具固定亮度之訊號所需的參考光的量之全像圖效率越大。
高折射性丙烯酸酯類在具低折射率的區域與具高折射率的區域之間能夠產生具高振幅(amplitude)之折射率光柵,及因而
在光聚合物配製物中能使全像圖具高DE與高△n。於此應注意到DE取決於△n與光聚合物層厚度d之乘積。於角度範圍的廣度下該全像圖是明顯地(被重建的),例如在單色照明(monochromatic illumination)之下,僅僅取決於層厚度d。
在利用白光之全像圖照明上,例如,能助於該全像圖重建之光譜範圍的廣度同樣僅僅取決於該層厚度d。d越小,各自的接受廣度越大。因此,若目的為欲產生明亮的且容易可見的全像圖時,目標是一高△n及一低厚度d,以使最大化DE。這意指,該△n越大,對於沒有DE損失的明亮的全像圖而言達到組態該層厚度d越自由。因此,在光聚合物配製物的最佳化中△n的最佳化有高重要性(P.Hariharan,Optical Holography,2nd Edition,Cambridge University Press,1996)。
WO 2008/125229揭示光聚合物配製物,其包含高分子量的單-及二官能性寫入單體。製自這些配製物的介質可用以寫入對數據儲存而言是良好適用性的反射全像圖,例如。然而,在該配製物之製造及加工中發生的問題:例如,存在的寫入單體具有一高黏度或高TG值(TG=玻璃轉移溫度)。這意指在該光聚合物配製物及一產生自其的介質中難以達到該寫入單體之均勻分布。再者,當使用已知配製物時,寫入單體黏聚物(agglomerates)可在該聚合物基質中形成,其大大地損害該介質或該曝露其中的全像圖之品質。在此種情況下,該全像材料變得模糊。
特殊形式的全像圖為透射(transmission)全像圖,其特點為,在該全像圖之製造過程中,參考光束(reference beam)及物體光束(object beam)照射來自同側的全像介質。透射全像圖發現各種用途。特別提及應是於此作為繞射性光學元件之光導件(light guide)。此種光學元件可用於需要諸如光譜學或天文學之應用。它們同樣適用於電子顯示器,例如用於3D顯示器。
因為該干涉物體的幾何形狀及訊號光束,在透射全像圖中的晶格間距(lattice spacing)相比於反射全像圖是大的。根據該波長,其可為介於500至1000nm。由於在該光聚合物中全像圖形成機
制為以該寫入單體之擴散為基礎,對遠遠不足擴散的寫入單體有需要具常用於透射全像圖之大晶格間距。然而,這對於能使成為高折射率對比度(△n)而言是必要條件。由該反射全像圖領域已知的光聚合物經常不適用於這目的,或不會產生一足夠高的折射率對比度。
WO 2012/020061敘述含有(甲基)丙烯酸酯基團與以硫醚類為基底的特定寫入單體,還有光聚合物配製物及包含彼等之介質,尤其是對於記錄透射全像圖。然而,用以製備該寫入單體之方法具有缺點:以此方式,在第一步驟中,環氧化物及硫醇在催化下經反應而得到羥基-官能性硫醚,其之後在第二步驟中與異氰酸酯-官能性丙烯酸酯類反應。然而,該硫醇的反應為一相當慢的反應,及難以達到常有高度氣味的反應物之全部轉換。在製造環境中這些材料的操控及反應容器的清潔還意味著一相對高度的成本及不方便性。再者,未轉換的游離硫醇抑制自由基聚合反應,還有將希望是確認所述的可以一不含硫醇的方式製備產物之替代品。
再者,WO 2012/020061及WO 2008/125199的寫入單體缺點為它們具有高黏度及為糊狀材料。由於該成分之效率、快速、均勻的混合是可達到的,這使其難以製造光聚合物配製物。再者,這些高-黏度寫入單體難以篩選及一般不利於操控。再者,還必須使用有機溶劑,其對於職業安全及環境保護是不利因素。再者,在全像介質(尤其是具高的層厚度)之製造中使用溶劑是不利的,因為它們只能(例如)以相當高度複雜方式從薄膜形式的介質中被移除,然而,於其情況下,會再次損害品質,例如以表面缺陷形式。然而,此種缺陷在許多情況下是不能接受的,因為對於它們意欲的高精確性光學功能該介質之後不再能達到。
再者,當該寫入單體在另外成分中具有高溶解度時,在光聚合物配製物的發展上通常是有利的。因此,於這情況下,在該配製物中的成分之定量比例可在相當廣範圍內改變,其相當容易適用於特定應用或實際上使其完全可以適用。
因此本發明之目的係提供一種在最初時特定類型之
光聚合物配製物,其中存在的寫入單體在不添加溶劑下快速且容易溶解。再者,應可以不使用硫醇下製備存在的寫入單體。最後,由該光聚合物配製物,應可以獲得具有低霧度之全像介質,i.e.在一光聚合物層厚度為>6μm下具有一霧度為低於5%,及具高於0.02之高折射率對比度(△n)的透射全像圖可被曝光至其內。
令人驚訝地,已發現,藉助本發明光聚合物配製物,可獲得尤其適用於記錄透射全像圖之全像介質。這些介質具有低霧度及另外地還予以一高折射率對比度(△n)。再者,存在的寫入單體可在不使用硫醇下被製備及可在該配製物中快速溶解且不添加溶劑。
M:鏡子
S:快門
SF:空間濾光器
CL:準直儀透鏡
PBS:偏振敏感性光束分離器
D:檢測器
I:虹膜式光圈
RD:轉盤參考方向
圖1為在λ=532nm(DPSS雷射=二極體泵的固態雷射)下全像介質測試器(HMT)之幾何圖形。
圖2為測得的繞射效率η(為圓圈)對角度失諧(angle detuning)△Ω及配合Kogelnik理論(為實線)繪圖。該圖係顯示實施例4.4。
圖3為測得的繞射效率η(為圓圈)對角度失諧△Ω及配合Kogelnik理論(為實線)繪圖。該圖係顯示實施例4.8。
式(I)之化合物可,例如,以二階段方法製備。在這方法中,在第一步驟,一單-至三官能性芳基縮水甘油醚可先與(甲基)丙烯酸反應。在適合的催化劑(例如膦類、鏻化合物、布忍斯特酸(Brnsted acids)或胺類)存在下,該加成反應較佳在該環氧乙烷(oxirane)的較少空間位阻側上實行,如此使形成比一級醇更多的二級醇。接著,所形成的醇類可被加成至異氰酸基烷基(甲基)丙烯酸酯上,得到主要具R1=(甲基)丙烯酸及R2=羰基胺基烷基(甲基)丙烯酸酯之化合物。下述通式系統再一次顯示合成策略。
同樣可以使用特定催化劑,其影響該(甲基)丙烯酸加成至該環氧化物上的位置選擇性(regioselectivity)。因此,可以使用
鈷(III)錯合物作為催化劑而只製備二級醇類(見A.Bukowska et al.,Journal of Molecular Catalysis A:Chemical 225(2005)7-10及其中引用文獻)。因此還可以獲得位置選擇性純的產物。
在一有利實施例中,在該式(I)之化合物中,在該芳香族系統中,該芳基基包含5至21個,較佳地5至18個,再較佳地6至16個與更佳地6至12個及最佳地6至10個碳原子及/或雜原子。
在該式(I)之化合物中,同樣有利的是當該芳基基由1至5個及較佳地1至3個相同或不同選自下述組群之取代基所取代的:正烷基,分支的烷基,烷氧基,苯基,苄基,苯基烷基,萘基,甲基硫基(methylthiyl),乙基硫基,烷基硫基,烷基硫基烷基,苯氧基,苯基硫基,萘基硫基,氟,氯,溴及/或碘,及較佳地由1至3個相同或不同選自甲基、乙基、硫基甲基、甲氧基、苯基之組群的取代基所取代的。
在該式(I)之化合物中,最適宜是當該芳基基為選自苯基、甲基苯基、乙基苯基、硫基甲基苯基、甲氧基苯基、聯苯基及萘基之組群。
還有利的是當R3為一基,選自-CH2-、-CH2CH2-、-CH(CH3)CH2-、-CH2CH(CH3)-、-CH2CH2CH2-、-CH2CH2CH2CH2-、-CH2CHOCH2CH2-、-CH2CH2OCH2CH2OCH2CH2-之組群及較佳地為一基選自-CH2CH2-、-CH(CH3)CH2-、-CH2CH(CH3)-、-CH2CH2CH2CH2-之組群,及最佳地-CH2CH2-。
在一另外實施例中,該R1基為一式(II)之基及該R2基為一式(III)之基,式中該R3基尤其是可為一-CH2CH2-基。或者是,該R1基可為一式(III)之基及該R2基為一式(II)之基,式中該R3基尤其是可為一-CH2CH2-基。
所用的基質聚合物B)可為非晶形熱塑性塑膠,例如聚丙烯酸酯類、聚甲基丙烯酸甲基酯類或甲基丙烯酸甲基酯的共聚物、甲基丙烯酸或其它丙烯酸烷基酯類及甲基丙烯酸烷基酯類,還有丙烯酸,例如聚丙烯酸丁基酯,還有聚乙酸乙烯酯及聚丁酸乙烯酯,其部分水解的衍生物,諸如聚乙烯醇類,及與乙烯化合物及/或另外(甲
基)丙烯酸酯類的共聚物,明膠類,纖維素酯類及纖維素醚類諸如甲基纖維素、乙醯丁酸纖維素酯,矽酮類,例如聚二甲基矽酮,聚胺基甲酸酯類,聚丁二烯類及聚異戊二烯類,還有聚氧化乙烯類,環氧樹脂,尤其是脂族環氧樹脂,聚醯胺類,聚碳酸酯類及在US 4994347A及之中所引用的系統。
然而,特別適宜是當該基質聚合物為聚胺基甲酸酯類。
特別適宜是當該基質聚合物已經交聯的。尤佳地當該基質聚合物已經三維上交聯的。環氧樹脂可為經陽離子性互交聯的。此外,還可以使用酸/酸酐、胺類、羥烷基醯胺及硫醇類作為交聯劑。
矽酮類可按一成分系統在水存在下(及選擇地在布忍斯特酸催化之下)經過縮合反應或按二成分系統藉矽質酯類(silicic esters)或有機錫化合物之加成反應而被交聯的。同樣可行是在乙烯基矽烷系統中氫矽烷化反應(hydrosilylation)。
不飽和化合物,例如丙烯醯基-官能性聚合物或不飽和酯類,可與胺類或硫醇類交聯。陽離子乙烯基醚聚合反應亦是可行的。
最適宜是當該基質聚合物經交聯的及尤其是三維上交聯的聚胺基甲酸酯類。
該聚胺基甲酸酯尤其是可藉至少一種多異氰酸酯成分a)與至少一種異氰酸酯-反應性成分b)之反應獲得。
該多異氰酸酯成分a)包含至少一種具有至少二個NCO基團之有機化合物。這些有機化合物尤其是可為單體的二-及三異氰酸酯類、多異氰酸酯類及/或NCO-官能性預聚物。該多異氰酸酯成分a)還可含有或由單體的二-及三異氰酸酯類、多異氰酸酯類及/或NCO-官能性預聚物之混合物構成。
所用的單體的二-及三異氰酸酯類可為本身對此項技術領域熟悉者為熟知的任何化合物,或其混合物。這些化合物可具有芳香族、芳脂族、脂族或環脂族結構。該單體的二-及三異氰酸酯
類還可包含少量的單異氰酸酯類,i.e.具有一個NCO基團之有機化合物。
適合的單體二-及三異氰酸酯類實例為丁烷1,4-二異氰酸酯、戊烷1,5-二異氰酸酯、己烷1,6-二異氰酸酯(六亞甲基二異氰酸酯,HDI)、2,2,4-三甲基六亞甲基二異氰酸酯及/或2,4,4-三甲基六亞甲基二異氰酸酯(TMDI)、異佛爾酮二異氰酸酯(IPDI)、1,8-二異氰酸基-4-(異氰酸基甲基)辛烷、雙(4,4’-異氰酸基環己基)甲烷及/或雙(2’,4-異氰酸基環己基)甲烷及/或其具有任何異構物含量之混合物、環己烷1,4-二異氰酸酯、該異構性雙(異氰酸基甲基)環己烷類、2,4-及/或2,6-二異氰酸基-1-甲基環己烷(伸六氫甲苯基2,4-及/或2,6-二異氰酸酯,H6-TDI)、伸苯基1,4-二異氰酸酯、伸甲苯基2,4-及/或2,6-二異氰酸酯(TDI)、伸萘基1,5-二異氰酸酯(NDI)、二苯基甲烷2,4’-及/或4,4’-二異氰酸酯(MDI)、1,3-雙(異氰酸基甲基)苯(XDI)及/或同系的1,4-異構物或前述化合物之任何所需的混合物。
適合的多異氰酸酯類為化合物其具有胺基甲酸酯、脲、碳二醯亞胺(carbodiimide)、醯脲、醯胺、異氰脲酸酯、脲甲酸酯(allophanate)、縮二脲、氧雜二嗪三酮(oxadiazinetrione)、脲二酮及/或亞胺氧雜二嗪二酮(iminooxadiazinedione)結構及為可獲自前述二-或三異氰酸酯類。
更佳地,該多異氰酸酯類為寡聚化的脂族及/或環脂族二-或三異氰酸酯類,其可以使用尤其是上述脂族及/或環脂族二-或三異氰酸酯類。
非常特別適宜是予以具有異氰脲酸酯、脲二酮及/或亞胺氧雜二嗪二酮結構之多異氰酸酯類,及以HDI為基底的縮二脲或其混合物。
適合的預聚物含有胺基甲酸酯及/或脲基團,及選擇地另外經過如上特定的NCO基團之改質形成的結構。這類預聚物可,例如,藉前述單體的二-及三異氰酸酯類及/或多異氰酸酯類a1)與異氰酸酯-反應性化合物b1)之反應獲得。
所用的異氰酸酯-反應性化合物b1)可為醇類、胺基
或巰基化合物,較佳地醇類。這些尤其是可為多元醇類。最佳地,所用的異氰酸酯-反應性化合物b1)可為聚酯多元醇類、聚醚醇類、聚碳酸酯多元醇類、聚(甲基)丙烯酸酯多元醇類及/或聚胺基甲酸酯多元醇類。
適合的聚酯多元醇類為,例如,線性聚酯二醇類或分支的聚酯多元醇類,其可以已知方式藉脂族、環脂族或芳香族二-或多羧酸或其酸酐與OH官能度2之多元醇類之反應獲得。適合的二-或多羧酸實例為多元羧酸諸如丁二酸、己二酸、辛二酸、癸二酸、癸烷二羧酸、鄰苯二甲酸、對苯二甲酸、間苯二甲酸、四氫鄰苯二甲酸或偏苯三酸(trimellitic acid),及酸酐諸如鄰苯二甲酸酐、偏苯三酸酐或丁二酸酐,或其任何所需的混合物。該聚酯多元醇類還可為以天然原料諸如蓖麻油為基底。同樣可行是該聚酯多元醇類為以內酯類之均-或共聚物為基底,其較佳地可藉內酯類或內酯混合物(諸如丁內酯、ε-己內酯及/或甲基-ε-己內酯)加成至羥基-官能性化合物(諸如OH官能度2之多元醇類,例如前述類型)上而獲得。
適合的醇類實例為全部的多元醇類,例如C2-C12二醇類、異構性環己烷二醇類、丙三醇或其任何所需的混合物。
適合的聚碳酸酯多元醇類可以本身已知方式藉有機碳酸酯類或光氣與二醇類或二醇混合物之反應獲得。
適合的有機碳酸酯類為二甲基、二乙基及二苯基碳酸酯。
適合的聚醚醇類為聚加成產物,選擇性嵌段式結構的產物,環狀醚類加成至OH-或NH-官能性起動劑分子上的產物。
適合的環狀醚類為,例如,氧化苯乙烯類、環氧乙烷、環氧丙烷、四氫呋喃、環氧丁烷、環氧氯丙烷,及其任何所需的混合物。
較佳的聚醚醇類為彼等前述只以環氧丙烷為基底的類型,或以環氧丙烷與另外1-環氧烷類為基底的無規或嵌段共聚物。特別適宜是予以環氧丙烷均聚物及含有氧伸乙基、氧伸丙基及/或氧伸丁基單元之無規或嵌段共聚物,此處該氧伸丙基單元的比例以全部氧伸乙基、氧伸丙基與氧伸丁基單元用量的總量為基準為至少20重量%,較佳地至少45重量%。氧伸丙基及氧伸丁基在此涵蓋全部各個線性及分支的C3及C4異構物。
另外適合作為該多元醇成分b1)之組分,作為多官能性、異氰酸酯-反應性化合物,亦為低分子量(i.e.具分子量500g/mol)、短鏈(i.e.含有2至20個碳原子)、脂族、芳脂族或環脂族二-、三-或多官能性醇類。
除了上述化合物外,這些可(例如)為新戊二醇、2-乙基-2-丁基丙烷二醇、三甲基戊烷二醇、位置上異構性二乙基辛烷二醇類、環己烷二醇、1,4-環己烷二甲醇、1,6-己烷二醇、1,2-及1,4-環己烷二醇、氫化的雙酚A、2,2-雙(4-羥基環己基)丙烷或2,2-二甲基-3-羥基丙酸、2,2-二甲基-3-羥基丙酸酯。適合的三醇類實例為三羥甲基乙烷、三羥甲基丙烷或丙三醇。適合的更高-官能度醇類為二(三羥甲基丙烷)、季戊四醇、二季戊四醇或山梨醇。
尤其適宜是當該多元醇成分為一二官能性聚醚、聚酯、或一聚醚-聚酯嵌段共聚酯或一具有一級OH官能之聚醚-聚酯嵌段共聚物。
同樣可以使用胺類作為異氰酸酯-反應性化合物b1)。適合的胺類實例為乙二胺、丙二胺、二胺基環己烷、4,4'-二環己基甲烷二胺、異佛爾酮二胺(IPDA)、二官能性多胺類,例如該Jeffamines®、胺-終端的聚合物,尤其是具有數目-平均莫耳質量10 000g/mol。同樣可使用前述胺類之混合物。
同樣可以使用胺醇類作為異氰酸酯-反應性化合物b1)。適合的胺醇類實例為該異構性胺基乙醇類、該異構性胺基丙醇
類、該異構性胺基丁醇類及該異構性胺基己醇類,或其任何所需的混合物。
全部前述異氰酸酯-反應性化合物b1)可如所需的彼此混合。
還適宜是當該異氰酸酯-反應性化合物b1)具有一數目-平均莫耳質量為200與10 000g/mol,再較佳地500與8000g/mol及最佳地800與5000g/mol。該多元醇類的OH官能度較佳為1.5至6.0,更佳地1.8至4.0。
該多異氰酸酯成分a)之預聚物尤其是可具有一游離單體的二-及三異氰酸酯類之殘餘量為<1重量%,更佳地<0.5重量%及最佳地<0.3重量%。
選擇地還可行是該多異氰酸酯成分a)含有,全部地或部分地,它的NCO基團已與由塗布技術已知的嵌段劑完全地或部分地反應之有機化合物。嵌段劑的實例為醇類、內醯胺類、肟類、丙二酸酯類、吡唑類、及胺類,例如丁酮肟、二異丙基胺、丙二酸二乙基酯、乙醯乙酸乙基酯、3,5-二甲基吡唑、ε-己內醯胺,或其混合物。
尤其適宜是當該多異氰酸酯成分a)包含具有脂族性鍵結的NCO基團之化合物,脂族性鍵結的NCO基團據了解意指彼等鍵結至一級碳原子之基團。該異氰酸酯-反應性成分b)較佳地包含至少一種具有平均為至少1.5個及較佳地2至3個異氰酸酯-反應性基團之有機化合物。在本發明內文中,異氰酸酯-反應性基團認為較佳是羥基、胺基或巰基基團。
該異氰酸酯-反應性成分尤其可包含具有一數目平均為至少1.5個及較佳地2至3個異氰酸酯-反應性基團之化合物。
成分b)之適合的多官能性異氰酸酯-反應性化合物為例如上述的化合物b1)。
又最適宜是當該聚胺基甲酸酯類為以聚酯C4聚醚醇類為基底。
成分C)之光起始劑為典型地藉由光化輻射的方式可活化的化合物,其可觸發該寫入單體之聚合反應。在該光起始劑之情
況下,在單分子(類型I)與雙分子(類型II)起始劑之間作出區分。此外,它們由作為用於自由基、陰離子性、陽離子性或混合型的聚合反應之光起始劑之化學本質來區分。
用於自由基光聚合反應之類型I光起始劑(Norrish類型I)在照射下經過單分子鍵斷裂(bond scission)而形成自由基。類型I光起始劑的實例為三嗪類、肟類、安息香醚類、二苯甲醯縮酮類(benzil ketals)、雙咪唑類、芳醯膦氧化物、鋶鹽類及錪鹽類。
用於自由基聚合反應之類型II光起始劑(Norrish類型II)由一作為敏化劑之染料與一共起始劑構成,及在符合該染料的光照射下經歷一雙分子反應。首先,該染料吸收一光子及轉移來自激發態的能量至該共起始劑。後者經過電子或質子轉移或直接氫抽取而釋放該聚合反應-觸發自由基。
在本發明內文中,適宜予以使用類型II光起始劑。
這類的光起始劑系統原則上敘述於EP 0 223 587 A及較佳由一或多種染料與烷芳基硼酸銨鹽(類)之混合物構成。
其(與一烷芳基硼酸銨鹽一起)形成一類型II光起始劑之適合的染料為敘述於WO 2012062655中的陽離子性染料,組合有同樣敘述於之中的陰離子化合物。
陽離子性染料據了解較佳意指選自下述類別:吖啶染料,呫噸(xanthene)染料,硫基呫噸染料,吩嗪(phenazine)染料,吩噁嗪(phenoxazine)染料,吩噻嗪(phenothiazine)染料,三(雜)芳基甲烷染料-尤其是二胺基-及三胺基(雜)芳基甲烷染料,單-、二-、三-及五次甲基花青(pentamethinecyanine)染料,半花青(hemicyanine)染料,外部陽離子性部花青染料,外部陽離子性中性花青(neutrocyanine)染料,零次甲基(zeromethine)染料-尤其是萘並內醯胺染料,鏈黴花青(streptocyanine)染料。這類染料被敘述,例如,於H.Berneth in Ullmann’s Encyclopedia of Industrial Chemistry,Azine Dyes,Wiley-VCH Verlag,2008,H.Berneth in Ullmann’s Encyclopedia of Industrial Chemistry,Methine Dyes and Pigments,Wiley-VCH Verlag,2008,T.Gessner,U.Mayer in Ullmann’s Encyclopedia of Industrial
Chemistry,Triarylmethane and Diarylmethane Dyes,Wiley-VCH Verlag,2000。
特別適宜是予以吩嗪染料,吩噁嗪染料,吩噻嗪染料,三(雜)芳基甲烷染料-尤其是二胺基-及三胺基(雜)芳基甲烷染料,單-、二-、三-及五次甲基花青染料,半花青染料,零次甲基染料-尤其是萘並內醯胺染料,鏈黴花青染料。
陽離子性染料的實例為Astrazon Orange G、Basic Blue 3、Basic Orange 22、Basic Red 13、Basic Violet 7、Methylene Blue、New Methylene Blue、Azure A、2,4-二苯基-6-(4-甲氧基苯基)吡喃鎓(pyrylium)、Safranin O、Astraphloxin、Brilliant Green、結晶紫、乙基紫及硫堇。
較佳的陰離子化合物尤其是C8-至C25-烷基磺酸鹽,較佳地C13-至C25-烷基磺酸鹽,C3-至C18-全氟烷基磺酸鹽,在烷基鏈中帶有至少3個氫原子之C4-至C18-全氟烷基磺酸鹽,C9-至C25-烷酸酯,C9-至C25-烯酸酯,C8-至C25-烷基硫酸鹽,較佳地C13-至C25-烷基硫酸鹽,C8-至C25-烯基硫酸鹽,較佳地C13-至C25-烯基硫酸鹽,C3-至C18-全氟烷基硫酸鹽,在烷基鏈中帶有至少3個氫原子之C4-至C18-全氟烷基硫酸鹽,以至少4個當量的環氧乙烷及/或4個當量的環氧丙烷為基底的聚醚硫酸鹽,雙(C4-至C25-烷基,C5-至C7-環烷基,C3-至C8-烯基或C7-至C11-芳烷基)磺基琥珀酸酯,由至少8個氟原子取代的雙-C2-至C10-烷基磺基琥珀酸酯,C8-至C25-烷基磺基乙酸酯類,由選自鹵素、C4-至C25-烷基、全氟-C1-至C8-烷基及/或C1-至C12-烷氧羰基之組群的至少一個基取代的苯磺酸鹽,選擇性由硝基、氰基、羥基、C1-至C25-烷基、C1-至C12-烷氧基、胺基、C1-至C12-烷氧羰基或氯取代的萘-或聯苯基磺酸鹽,選擇性由硝基、氰基、羥基、C1-至C25-烷基、C1-至C12-烷氧基、C1-至C12-烷氧羰基或氯取代的苯-、萘-或聯苯基二磺酸鹽,由二硝基、C6-至C25-烷基、C4-至C12-烷氧羰基、苄醯基、氯苄醯基或甲苯基取代的苯甲酸酯,萘二羧酸之陰離子,二苯基醚二磺酸鹽,脂族C1至C8醇類或丙三醇之磺酸化的或硫酸化的、選擇性至少單不飽和的C8至C25脂肪酸酯類,雙(磺基-C2-至C6-烷基)C3-至C12-烷二羧酸酯類,雙(磺基
-C2-至C6-烷基)伊康酸酯類,(磺基-C2-至C6-烷基)C6-至C18-烷羧酸酯類,(磺基-C2-至C6-烷基)丙烯酸酯類或甲基丙烯酸酯類,選擇性由至多12個鹵素基取代的參兒茶酚磷酸鹽(triscatechol phosphate),選自四苯基硼酸鹽、氰基三苯基硼酸鹽、四苯氧基硼酸鹽、C4-至C12-烷基三苯基硼酸鹽之組群的陰離子,其中該苯基或苯氧基基可由鹵素、C1-至C4-烷基及/或C1-至C4-烷氧基所取代的,C4-至C12-烷基三萘基硼酸鹽,四-C1-至C20-烷氧基硼酸鹽,7,8-或7,9-二碳代-巢-十一硼酸鹽(1-)或(2-),其選擇性在硼及/或碳原子上由一或二個C1-至C12-烷基或苯基基團所取代的,十二氫二碳代十二硼酸鹽(2-)或B-C1-至C12-烷基-C-苯基十二氫二碳代十二硼酸鹽(1-),此處,在多價陰離子化合物諸如萘二磺酸鹽之情況下,A-代表一當量的這陰離子,及此處該烷及烷基基團可為分支的及/或可為由鹵素、氰基、甲氧基、乙氧基、甲氧基羰基或乙氧基羰基所取代的。
還適宜是當該染料之陰離子A-具有AClogP於1至30之範圍時,更佳地於1至12之範圍及尤佳地於1至6.5之範圍。計算AClogP係根據J.Comput.Aid.Mol.Des.2005,19,453;Virtual Computational Chemistry Laboratory,http://www.vcclab.org。
適合的烷芳基硼酸銨鹽為,例如(Cunningham et al.,RadTech'98 North America UV/EB Conference Proceedings,Chicago,Apr.19-22,1998):三苯基己基硼酸四丁基銨鹽,三苯基丁基硼酸四丁基銨鹽,三萘基己基硼酸四丁基銨鹽,參(4-第三-丁基)苯基丁基硼酸四丁基銨鹽,參(3-氟苯基)己基硼酸四丁基銨鹽([191726-69-9],CGI 7460,product from BASF SE,Basle,Switzerland),二戊基二苯基硼酸1-甲基-3-辛基咪唑及參(3-氯-4-甲基苯基)己基硼酸四丁基銨鹽([1147315-11-4],CGI 909,產品得自BASF SE,Basle,Switzerland)。
可有利的是使用這些光起始劑之混合物。根據所用的輻射源,光起始劑的類型及濃度必須以此項技術領域熟悉者已知的方式被調整。進一步詳細內容被敘述,例如,於P.K.T.Oldring(Ed.),Chemistry & Technology of UV & EB Formulations For Coatings,Inks & Paints,vol.3,1991,SITA Technology,London,p.61-328。
最適宜是當該光起始劑包含一吸收光譜至少部分涵蓋400至800nm之光譜範圍之染料,與至少一種搭配該染料之共起始劑,之組合物時。
還適宜是當至少一種適用於一選自藍色、綠色及紅色之雷射光顏色之光起始劑存在於該光聚合物配製物中。
還進一步適宜是當該光聚合物配製物含有一種適用於各自選自藍色、綠色及紅色之至少二種雷射光顏色之光起始劑時。
最後,最適宜是當該光聚合物配製物含有一種適用於各個雷射光顏色藍色、綠色及紅色之光起始劑時。
當該光聚合物配製物包含,如另外寫入單體A),以及式(I)之寫入單體(較佳地一丙烯酸酯-或甲基丙烯酸酯-官能性寫入單體)時,可達到特別高的折射率對比度。特別適宜是予以單官能性寫入單體及尤其是予以彼等敘述於US 2010/0036013 A1之單官能性胺基甲酸酯(甲基)丙烯酸酯類。
適合的丙烯酸酯寫入單體尤其是通式(IV)之化合物
其中n1且n4及R5為一未取代的或者選擇性由雜原子取代的線性、分支的、環狀的或雜環狀有機基及/或R6為氫或一未取代的或者選擇性由雜原子取代的線性、分支的、環狀的或雜環狀的有機基。更佳地,R6為氫或甲基及/或R5為一未取代的或者選擇性由雜原子取代的線性、分支的、環狀的或雜環狀的有機基。
丙烯酸酯類及甲基丙烯酸酯類分別係指丙烯酸及甲基丙烯酸之酯類。較佳可用的丙烯酸酯類及甲基丙烯酸酯類的實例為丙烯酸苯基酯、甲基丙烯酸苯基酯、丙烯酸苯氧基乙基酯、甲基丙烯酸苯氧基乙基酯、丙烯酸苯氧基乙氧基乙基酯、甲基丙烯酸苯氧基乙氧基乙基酯、丙烯酸苯基硫基乙基酯、甲基丙烯酸苯基硫基乙基酯、
丙烯酸2-萘基酯、甲基丙烯酸2-萘基酯、丙烯酸1,4-雙(2-硫基萘基)-2-丁基酯、甲基丙烯酸1,4-雙(2-硫基萘基)-2-丁基酯、雙酚A二丙烯酸酯、雙酚A二甲基丙烯酸酯,及其乙氧化的類似化合物,N-咔唑基丙烯酸酯類。
胺基甲酸酯丙烯酸酯類據了解意指具有至少一個丙烯酸酯基團及至少一個胺基甲酸酯鍵之化合物。這類化合物可,例如,藉使一羥基-官能性丙烯酸酯或甲基丙烯酸酯與一異氰酸酯-官能性化合物之反應而獲得。
可用於這目的之異氰酸酯-官能性化合物實例為單異氰酸酯類,及依a)提及之單體的二異氰酸酯類、三異氰酸酯類及/或多異氰酸酯類。適合的單異氰酸酯類實例為苯基異氰酸酯、該異構性甲基硫基苯基異氰酸酯類。以上已提及二-、三-或多異氰酸酯類,還有三苯基甲烷4,4‘,4“-三異氰酸酯及參(p-異氰酸基苯基)硫基磷酸鹽或其與胺基甲酸酯、脲、碳二醯亞胺、醯脲、異氰脲酸酯、脲甲酸酯、縮二脲、氧雜二嗪三酮、脲二酮、亞胺氧雜二嗪二酮結構之衍生物及其混合物。適宜予以芳香族二-、三-或多異氰酸酯類。
適用於胺基甲酸酯丙烯酸酯類製備的羥基-官能性丙烯酸酯類或甲基丙烯酸酯類包括,例如,化合物諸如(甲基)丙烯酸2-羥基乙基酯、聚氧化伸乙基單(甲基)丙烯酸酯類、聚氧化伸丙基單(甲基)丙烯酸酯類、聚氧化伸烷基單(甲基)丙烯酸酯類、聚(ε-己內酯)單(甲基)丙烯酸酯類,例如Tone®M100(Dow,Schwalbach,DE),(甲基)丙烯酸2-羥基丙基酯、(甲基)丙烯酸4-羥基丁基酯、(甲基)丙烯酸3-羥基-2,2-二甲基丙基酯、(甲基)丙烯酸羥基丙基酯、丙烯酸2-羥基-3-苯氧基丙基酯,多元醇類諸如三羥甲基丙烷、丙三醇、季戊四醇、二季戊四醇、乙氧化的、丙氧化的或烷氧化的三羥甲基丙烷、丙三醇、季戊四醇、二季戊四醇或其技術性混合物之羥基-官能性單-、二-或四丙烯酸酯類。適宜予以丙烯酸2-羥基乙基酯、丙烯酸羥基丙基酯、丙烯酸4-羥基丁基酯及聚(ε-己內酯)單(甲基)丙烯酸酯。
同樣可以使用基本上已知的具有OH含量為20至300mg KOH/g之含有羥基的環氧基(甲基)丙烯酸酯類或具有OH含量為20
至300mg KOH/g之含有羥基的聚胺基甲酸酯(甲基)丙烯酸酯類或具有OH含量為20至300mg KOH/g之丙烯酸酯化的聚丙烯酸酯類及其混合物,及與含有羥基的不飽和的聚酯之混合物及與聚酯(甲基)丙烯酸酯類之混合物或含有羥基的不飽和的聚酯與聚酯(甲基)丙烯酸酯類之混合物。
尤其適宜是予以胺基甲酸酯丙烯酸酯類,其可獲自參(p-異氰酸基苯基)硫基磷酸鹽及/或m-甲基硫基苯基異氰酸酯與醇-官能性丙烯酸酯類(諸如(甲基)丙烯酸羥基乙基酯、(甲基)丙烯酸羥基丙基酯及/或(甲基)丙烯酸羥基丁基酯)之反應。
同樣可行是該寫入單體包含或由另外不飽和化合物構成,諸如α,β-不飽和羧酸衍生物,例如馬來酸酯類、富馬酸酯類、馬來醯亞胺類、丙烯醯胺,還有乙烯基醚類、丙烯基醚類、烯丙基醚類及含有二環戊二烯基單元之化合物,還有烯烴性不飽和化合物,例如苯乙烯、α-甲基苯乙烯、乙烯基甲苯及/或烯烴類。
在一另較佳的實施例中,該光聚合物配製物另外包含單體的氟胺基甲酸酯類。
特別適宜是當該氟胺基甲酸酯類包含或由至少一種式(V)之化合物構成
其中m1且m8及R7、R8、R9各自獨立地為氫或未取代的或者是選擇性由雜原子取代的線性、分支的、環狀的或雜環狀的有機基,此處較佳地該R7、R8、R9基之至少一者由至少一個氟原子取代的及,更佳地,R7為一具有至少一個氟原子之有機基。
在本發明之另外較佳的實施例中,該光聚合物配製物包含10%至89.999重量%(較佳地20%至70重量%)的基質聚合物,3%至60重量%(較佳地10%至50重量%)的寫入單體,0.001%至5重量%(較
佳地0.5%至3重量%)的光起始劑及選擇性0%至4重量%(較佳地0至2重量%)的催化劑、0%至5重量%(較佳地0.001%至1重量%)的穩定劑、0%至40重量%(較佳地10%至30重量%)的單體的氟胺基甲酸酯類及0%至5重量%(較佳地0.1%至5重量%)的另外添加劑,此處全部組分之總和為100重量%。
所用的催化劑可為胺基甲酸酯化(urethanization)催化劑,例如鉍、錫、鋅或鐵之有機或無機衍生物(亦見於2012/062658中所特定的化合物)。特佳的催化劑為丁基錫參(2-乙基己酸酯)、鐵(III)參乙醯丙酮酸酯、鉍(III)參(2-乙基己酸酯)及錫(II)雙(2-乙基己酸酯)。此外,還可以使用空間位阻的胺類作為催化劑。
所用的穩定劑可為a)自由基抑制劑,例如酚類諸如對-甲氧基酚,2,6-二-第三-丁基-4-甲基酚(紫羅蘭醇(ionol)),及寡聚的紫羅蘭醇類(e.g.十八基3-(3,5-二-第三-丁基-4-羥基苯基)丙酸酯),還有所謂的HALS胺類(e.g.N,N’-雙甲醯基-N,N’-雙-(2,2,6,6-四甲基-4-哌啶基)六亞甲基二胺)、N-烷基-HALS、N-烷氧基-HALS及N-烷氧基乙基-HALS化合物,還有吩噻嗪;b)抗氧化劑,例如二膦酸酯類、二硫化物及硫醚類;及/或c)UV吸收劑,諸如氰基丙烯酸酯類(e.g.2-氰基-3,3-二苯基丙烯酸乙基酯)、苯並三唑類(e.g.2-(2H-苯並三唑-2-基)-4,6-雙(1-甲基-1-苯基乙基)酚)、二苯甲酮類(e.g.2-羥基-4-辛基氧基二苯甲酮)、苯並三唑類(e.g.2-(2-羥基苯基)苯並三唑)及草醯替苯胺類(oxanilides)。
所用的另外添加劑可為
a)整平助劑(levelling aids)(濕潤助劑),例如聚丙烯酸酯類、矽酮類、混成聚合物(e.g.矽化的丙烯酸酯類),其顯著的是用於調整表面張力,及/或
b)抗靜電劑
c)觸變劑
d)增稠劑及/或
e)殺生物劑。
特別適宜是予以使用光聚合物配製物,其包含20%至70重量%的基質聚合物,20%至50重量%的寫入單體,0.001%至5重量%的光起始劑,0%至2重量%的催化劑,0.001%至1重量%的自由基穩定劑,選擇性10%至30重量%的氟胺基甲酸酯類及選擇性0.1%至5重量%的另外添加劑。
本發明還提供一種特別以薄膜形式之全像介質,其包含一本發明之光聚合物配製物或可藉使用一本發明之光聚合物配製物獲得。本發明又再提供一種本發明之光聚合物配製物於全像介質製造之用途。
在一根據本發明全像介質之較佳實施例中,至少一種全像圖已曝光至該全像介質內。
更特別地,該全像圖可為一反射、透射、同軸(in-line)、離軸(off-axiss)、全孔轉移(full-aperture transfer)、白光透射、Denisyuk、離軸反射或邊緣光(edge-lit)全像圖,或者是一全像立體圖,及較佳地一反射、透射或邊緣光全像圖。
該全像圖之可行的光學功能符合光元件諸如透鏡、鏡子、偏向鏡、濾光鏡、散光鏡片、導向擴散元件、繞射元件、光導件、波導件、投影鏡片及/或光罩之光學功能。此外,多種此光學功能可以諸如全像圖而被組合,例如如此使該光以不同方向根據光之入射而偏轉。例如,可以利用此設置建立自動立體的或全像電子顯示器,其在沒有進一步幫助(例如偏光鏡(polarizer)或快門鏡片(shutter glasses))下容許一欲經歷的用於汽車平視顯示器或頭戴顯示器之立體視覺印象。
這些光學元件,根據該全像圖如何已被曝光及該全像圖的尺寸,經常具有一特定的頻率選擇性。尤其是當使用單色光源諸如LED或雷射光時這是重要的。例如,按照補色(RGB)需要一個全像圖,為了依一頻率選擇方式偏轉光且同時為了能使全色顯示。因此,特別是顯示器設置,數個全像圖在該介質中依一重疊方式必須被曝光。
此外,藉由本發明介質之方式,還可以產生全像影像或表徵(representations),一般例如對於個人肖像、於安全文件中的生物識別表徵,或對於廣告、安全標籤、品牌保護、品牌、標籤、設計元件、裝飾品、圖表、收藏卡、影像及類似物之影像或影像結構,還有可表示數位數據之影像,包括與以上詳述的產品之組合。全像影像可具有三維的影像之印象,而根據由其之角度及含其之光源(包括移動光源)等等它們還可表示影像連續鏡頭、短片或多種不同物體,它們係經照射的。因為這可行設計之多變性,對於上述應用之全像圖(尤其是體積全像圖)構成一引人注目的技術解決方案。使用廣泛多變的不同曝光方法(位移、空間或角度多工法),對於數位數據之儲存還可以使用此全像圖。
本發明還提供一種藉使用本發明之光聚合物配製物製造全像介質之方法。
因此,該光聚合物配製物尤其是可用於薄膜形式的全像介質之製造。在這情況下,對在可見光譜範圍(在400至780nm之波長範圍內透射率大於85%)內對光透明的一材料或材料複合物之層片(ply)作為載體基材被塗布在一或兩面上,及一覆蓋層係選擇性施用至該光聚合物一層片或積層片上。
對於該載體基材之較佳材料或材料複合物為以聚碳酸酯(PC)、聚對苯二甲酸乙二酯(PET)、聚對苯二甲酸丁二酯、聚乙烯、聚丙烯、纖維素乙酸酯、纖維素水合物、纖維素硝酸鹽、環烯烴聚合物、聚苯乙烯、聚環氧化物、聚碸、纖維素三乙酸酯(CTA)、聚醯胺(PA)、聚甲基丙烯酸甲基酯(PMMA)、聚氯乙烯、聚乙烯丁醛或聚二環戊二烯或其混合物為基底。它們更佳為以PC、PET、PA、PMMA及CTA為基底。材料複合物可為薄膜層壓體或共擠壓體。較佳的材料複合物為根據系統A/B、A/B/A或A/B/C之一者形成的雙層及三層膜。特別適宜是予以PC/PET、PET/PC/PET及PC/TPU(TPU=熱塑性聚胺基甲酸酯)。
該載體基材之材料或材料複合物可予以在一或兩面上防黏、抗靜電、疏水化或親水化加工(finish)。所提及的改質作用,
在面向該光聚合物層的面上,目的係提供使該光聚合物層片在沒有破壞下可從該載體基材分開。從該光聚合物層片之載體基材之相反面的改質作用提供確保本發明介質滿足現有的特定的機械需求,例如,在輥層壓機上加工之情況下,尤其是在輥-對-輥程序上。
本發明同樣提供一種包含本發明全像介質之光學顯示器。
此光學顯示器的實例為以液晶為基底的成像顯示器,有機發光二極體(OLEDs),LED顯示器面板,以繞射光選擇性為基礎的微電機系統(MEMS),電潤濕顯示器(E-ink)及電漿顯示器螢幕。這類光學顯示器可為自動立體的及/或全像顯示器、透射性與反射性投影螢幕、具可切換的限制發光特性的顯示器(對於隱密濾光鏡而言)與雙向多用戶螢幕、虛擬顯示器、平視顯示器、頭戴顯示器、照明標誌、警示燈、訊號燈、泛光燈及顯示器面板。
此外,本發明還提供一種本發明全像介質用於晶片卡、身分證件、3D影像、產品保護標籤、標籤、鈔票或全像光學元件之製造之用途,尤其是對於視覺顯示器。
還適宜是當芳基基為由1至5個及較佳地1至3個相同或不同取代基所取代的,該取代基選自正烷基、分支的烷基、烷氧基、苯基、苄基、苯基烷基、萘基、甲基硫基、乙基硫基、烷基硫基、烷基硫基烷基、苯氧基、苯基硫基、萘基硫基、氟、氯、溴及/或碘之組群,及較佳地由選自甲基、乙基、硫基甲基、甲氧基、苯基之組群的1至3個相同或不同取代基所取代的。
實施例
本發明在下文中藉實施例詳細說明。
圖式顯示:圖1為在λ=532nm(DPSS雷射=二極體泵的固態雷射)下全像介質測試器(HMT)之幾何圖形,及圖2為測得的繞射效率η(為圓圈)為對角度失諧(angle detuning)△Ω及配合Kogelnik理論(為實線)繪圖。該圖係顯示實施例4.4。
圖3為測得的繞射效率η(為圓圈)為對角度失諧△Ω及配合Kogelnik理論(為實線)繪圖。該圖係顯示實施例4.8。
試驗方法:
黏度測定:
黏度,利用一Physica MCR 51(得自Anton Paar)黏度
劑測定。對於這目的,平衡化該樣品及懸掛一球體(對低黏度η<10 000mPas:23℃,球直徑25mm(CP-25)及對高黏度η>10 000mPas:50℃,球直徑60mm(CP-60))。將約0.5至1g的產品放置在板上,及讓該球體降下,如此致該球體全部潤濕有產物。將多餘的產物拭去。藉該儀器自動設定剪切速率(在較低黏度下約500 l/s及在較高黏度下約100 l/s)。各案例作20次測量及測定該平均值。
折射率測定:
對於高-黏度及固體產物,該折射率於589nm波長下測定,使藉由該透射與反射光譜作為樣品的波長函數而獲得該折射率n。對於這目的,由一於乙酸乙酯的五重量百分比溶液將厚度約100至300mm的樣品薄膜旋塗至石英載玻片(quartz glass slides)上。這層組件之透射與反射光譜利用得自STEAG ETA-Optik之CD-Measurement System ETA-RT光譜儀測量,及之後該層厚度及該n的光譜輪廓與該測得的透射與反射光譜配合。這係利用光譜儀的內部軟體完成的及另外需要該石英玻璃基材的n數據,其事先在一空白測量中測定的。
對於液體產物,一Abbe折射儀用以於589nm下測定折射率。這係藉將3滴的產物施用至該儀器之經清潔的測量稜鏡上而完成的,摺下該照明稜鏡及之後在2分鐘內平衡化至20℃。接著,在觀察範圍中,將該亮/暗邊界精確地定位至該折射儀的十字準線上。一旦在所設數值上不再有任何變動時,在該儀器上讀出該折射率至小數點四位數。進行兩次測定。可允許至多0.0002刻度(scale division)之差值。
霧度測量
霧度依ASTM D 1003測量。該霧度為從所發射的光束平均偏離大於2.5°之透射的光之百分率。欲測量該霧度,在測量前該全像試樣在外面先被清洗,為了避免在玻璃表面上由指紋及灰塵產生畸變結果。之後將該試樣插入用於分析之Byk-Gardner Haze-Gard-Plus儀器內。該試樣的層厚度,按照以下在"藉由在透射配置中的雙光束干涉之方式測量全像性質DE及全像介質的△n"段落中所述,根據Kogelnik依理論Bragg曲線之模擬,測量。
對寫入單體的溶解時間之測量
將1.47g的多元醇成分引入一平板形管(tablet tube)內,附有攪拌棒及該平板形管被定位在一磁攪拌器上。接著,添加1.00g的欲測試的寫入單體同時攪拌及測定欲形成一視覺上清晰、均勻溶液所花費時間。
異氰酸酯含量
記錄的NCO值(異氰酸酯含量),依DIN EN ISO 11909測定。
在一反應混合物中,藉IR光譜偵測到NCO基團之全部轉換率(i.e.其不存在)。因此,完全轉換率係被假設當在該反應混合物之IR光譜中沒有看到任何NCO鍵(2261cm-1)時。
固體含量
一未塗漆的錫罐蓋子及一迴紋針用以確定空種(tare weight)。之後秤取約1g的欲分析的樣品及接著利用適當彎曲的迴紋針均勻地分布於該錫罐蓋子。該迴紋針留在該用於測量之樣品中。測定起始重量,之後在實驗室烘箱中於125℃下加熱該組件1小時,及接著測定最後重量。該固體含量藉下述方程式測定:最後重量[g]* 100/起始重量[g]=固體之重量%。
藉由在透射配置中的雙光束干涉之方式測量全像性質DE及該全像介質之△n
所製得的介質,藉由根據如下述圖1之測量設置方式測試它們的全像性質:圖1顯示全像試驗設置,利用其測量該介質之繞射效率(DE),具下述標示:M=鏡子,S=快門,SF=空間濾光器,CL=準直儀透鏡,λ/2=λ/2板,PBS=偏振敏感性光束分離器,D=檢測器,I=虹膜式光圈,α0=-22.3°,β0=22.3°為在該樣品外面(該介質外面)所測得的連貫光束(coherent beams)之入射角度。RD=轉盤的參考方向。
一DPSS雷射之光束(發射波長532nm)藉空間濾光器(SF)及連同視準透鏡(CL)之幫助被轉換成一平行均勻光束。該訊號與
參考光束之最後截面藉該虹膜式光圈(I)校準。該虹膜式光圈開口之直徑為0.4cm。該偏振相關的光束分離器(PBS)將該雷射光束分裂成二個相同偏振之連貫光束。藉由該λ/2板之方式,該參考光束之功率設至2.0mW及該訊號光束之功率設至2.0mW。該等功率係使用半導體檢測器(D)隨著移除樣品而被測定。該參考光束之入射角(α0)為-22.3°;該訊號光束之入射角(β0)為22.3°。該等角度係從正交於該光束方向之樣品持續進行測量。根據圖1,因此,α0具有一負號及β0具有一正號。在該樣品(介質)之位置,該二種重疊光束(overlapping beams)之干涉場產生一平行於在該樣品(透射全像圖)上入射的二種光束之角度等分線(bisectors)之亮與暗帶之圖案。該帶間距Λ,亦稱為光柵週期(grating period),在該介質中為~700nm(該介質之折射率假設為~1.504)。
全像圖依下述方式被記錄於該介質中:
●對於曝光時間t兩個快門(S)為打開的
●其後,隨著快門(S)關閉,該介質被容許迄此尚未聚合的寫入單體擴散5分鐘。
所記錄的全像圖之後依下述方式被重建。該訊號光束之快門仍是關著的。該參考光束之快門為開著的。該參考光束之虹膜式光圈為接近一直徑<1mm。這確保該光束對於該介質之全部旋轉角度(Ω)而言一直完全在該先前記錄的全像圖內。該轉盤,在電腦控制下,掃過自Ωmin至Ωmax之具一角度步距寬度(step width)為0.05°之整個角度範圍。Ω由正交於該轉盤之參考方向的樣品被測得。該轉盤之參考方向(Ω=0)係在當參考光束之入射角及該訊號光束之入射角在全像圖記錄上具有相同絕對值時獲得的,i.e.α0=-22.3°及β0=22.3°。通常,下述是在一對稱性透射全像圖之寫入(記錄)的過程中該干涉場的真值(α0=-β0):α0=θ0 θ0為在實驗室系統中的介質外面的半角度。因此,在這情況下,θ0=-22.3°。在各個旋轉角度Ω之設定下,在第零階透射的光束之功率藉由對應檢測器D之方式測得,及在第一階繞射的光束之功率藉由檢測器
D之方式測得。該繞射效率在各個角度Ω之設定下按照下式計算商值:
P D 為在該檢測器中對於繞射光束之功率及P T 為在該檢測器中對於透射的光束之功率。
藉由上述方法之方式,該Bragg曲線,其說明該繞射效率η為一旋轉角度Ω對記錄的全像圖之函數,被測得及儲存在電腦上。此外,透射至第零階內的強度還針對旋轉角度Ω被記錄及儲存在電腦上。
該全像圖之中心繞射效率(DE=η0)於Ω=0測定。
該折射率對比度△n及該光聚合物層之厚度目前配合藉由耦合波理論之方式測得的Bragg曲線(見:H.Kogelnik,The Bell System Technical Journal,Volume 48,November 1969,Number 9 page 2909-page 2947)。評估方法敘述於下文:對於一透射全像圖之Bragg曲線η(Ω),根據Kogelnik:
與:
在該Bragg條件下,該"移相(dephasing)" DP=0。及它對應上遵循:α0=θ0
sin(α0)=n.sin(α)ν為光柵厚度及ξ為已記錄的折射率光柵之失諧參數(detuning parameter)。n為該光聚合物之平均折射率及被設定至1.504。λ為在真空中雷射光之波長。
所測得的繞射效率之數據及該理論Bragg曲線對旋轉角度Ω繪圖,如圖2及圖3所示。
由於DE為已知的,該理論Bragg曲線之形狀,根據Kogelnik,僅由該光聚合物層的厚度d所測定的。△n係經由一給定厚度d之DE校正如此使對於DE之測量及理論總是一致的。因而調整d直到該第一次要最小的角度位置及該對應第一次要最小的角度位置之理論Bragg曲線之第一次要最大的高度及該測得的Bragg曲線之第一次要最大的高度。
圖2及圖3顯示藉耦合波理論(亦稱為Kogelnik理論)配合該實驗數據理論上計算的Bragg曲線η(為實線),及顯示,用於比較,該實驗上測定的繞射效率(以圓形符號)對旋轉角度Ω繪圖。
對於一配製物,重複這程序,可能是數次,對於在不同介質上不同曝光時間t,為了在△n到達飽和值之全像圖記錄過程中找到入射的雷射光束之平均能量劑量。該平均能量劑量E如下述由指定為該角度α0及β0的二種成分光束之功率計算得(參考光束此處Pr=2.00mW,及訊號光束此處Ps=2.00mW),該曝光時間t及該虹膜式光圈之直徑(0.4cm):
化學試劑:
在各案例中,該CAS號碼,若是已知的,以方括號表述。
m-甲酚 [108-39-4]-ABCR GmbH & Co KG,Karlsruhe,Germany
3-乙基酚 [620-17-7]-Fluka/Sigma-Aldrich Chemie GmbH,Steinheim,Germany
3-(甲基硫基)酚 [1073-29-6]-ABCR GmbH & Co KG,Karlsruhe,Germany
4-(甲基硫基)酚 [1073-72-9]-Sigma-Aldrich Chemie GmbH,Steinheim,Germany
碳酸鉀 Sigma-Aldrich Chemie GmbH,Steinheim,Germany
環氧溴丙烷(Epibromohydrin) [3132-64-7]-Sigma-Aldrich Chemie GmbH,Steinheim,Germany
苯基縮水甘油醚 Denacol EX141;Nagase ChemteX Corporation,Osaka,Japan
三苯基膦 [603-35-0]ABCR GmbH & Co KG,Karlsruhe,Germany
丙烯酸 [79-10-7]Acros Organics,Geel,Belgium
甲基丙烯酸 [79-41-4]Acros Organics,Geel,Belgium
紫羅蘭醇(Ionol) [128-37-0]Merck KGaA,Darmstadt,Ger-many
2-[(聯苯基-2-基氧基)甲基]環氧乙烷 Denacol EX142;Nagase ChemteX Corporation,Osaka,Japan
2-[(2-甲基苯氧基)甲基]環氧乙烷 [2210-79-9]Sigma-Aldrich Chemie GmbH,Steinheim,Germany
丙烯酸2-異氰酸基乙基酯 [13641-96-8]-Karenz® AOI,SHOWA DENKO K.K.,Fine Chemicals Group,Specialty Chemicals Department,Chemicals Division,Japan
甲基丙烯酸2-異氰酸基乙基酯 [30674-80-7]-Karenz® MOI,SHOWA DENKO K.K.,Fine Chemicals Group,Specialty Chemicals Department,Chemicals Division,Japan
1,2-環己胺基-N,N’-雙(3,5-二-t-丁基亞柳基)鈷(III)p-甲苯磺酸鹽單水合物 [672306-06-8]ABCR GmbH & Co KG,Karlsruhe,Germany
1-異氰酸基-3-(甲基硫烷基)苯 [28479-19-8]-Sigma-Aldrich Chemie GmbH,Steinheim,Germany
硫基磷酸參(p-異氰酸基苯基)鹽 Desmodur® RFE,產品得自Bayer MaterialScience AG,Leverkusen,Germany
二月桂酸二丁基錫鹽 [77-58-7]-胺基甲酸酯化催化劑Desmorapid Z,Bayer MaterialScience AG,Leverkusen,Germany
Fomrez® UL 28 胺基甲酸酯化催化劑,商品得自Momentive Performance Chemicals,Wilton,CT,USA.
Addocat® SO 一錫系催化劑,得自RheinChemie,Mannheim,Germany
Desmodur® N 3900 產品得自Bayer MaterialScience AG,Leverkusen,DE,己烷二異氰酸酯-系多異氰酸酯,亞胺氧雜二嗪二酮的比例為至少30%,NCO含量:23.5%。
CGI-909 參(3-氯-4-甲基苯基)(己基)硼酸四丁基銨鹽[1147315-11-4]為一產品得自BASF SE(formerly Ciba Inc.)。
三甲基六亞甲基二異氰酸酯 [28679-16-5]-ABCR GmbH & Co KG,Karlsruhe,Germany
1H,1H-7H-全氟庚-1-醇 [335-99-9]-ABCR GmbH & Co KG,Karlsruhe,Germany
結晶紫 [548-62-9]Sigma-Aldrich Chemie GmbH,Steinheim,Germany
Irgacure® 250 [344562-80-7],錪,(4-甲基苯基)[4-(2-甲基丙基)苯基]-,六氟磷酸鹽(1-),產品得自BASF SE
本發明寫入單體:
用於製備環氧乙烷之一般方法(實施例1.5至1.7;其它使用的環氧乙烷為商業上可取得的)
將1當量的酚與2.4當量的碳酸鉀初始裝入2-丁酮中。然後於室溫下慢慢添加3當量的環氧溴丙烷。2-丁酮用量相當於總用量的50重量百分比。初步檢查該酚是否充分溶解於2-丁酮中。該碳酸鉀懸浮液之後在迴流下沸騰。
一旦已達到全部轉換,藉1H NMR光譜檢查(見以下時間論述),將該碳酸鉀濾出及在一旋轉蒸發器上濃縮該混合物。在沒有進一步的處理下,此得到液態、澄清的產物,某些產物為有色的。以所用的酚為基準定量產率。
實施例1.5 2-[(3-甲基苯氧基)甲基]環氧乙烷
反應物:11.9g m-甲酚
45.2g 環氧溴丙烷
36.4g 碳酸鉀
93.4g 2-丁酮
條件:於86℃下16.5小時及於70℃下49.5小時
1H NMR(CDCl3,400MHz):δ(1H)=7.18(t,1H),6.77(d,1H),6.68-6.75(m,2H),4.18(dd,1H),3.95(dd,1H),3.24(m,1H),2.89(dd,1H),2.73(dd,1H),2.32(s,3H)。
實施例1.6 2-[(3-乙基苯氧基)甲基]環氧乙烷
反應物:12.2g 3-乙基酚
41.1g 環氧溴丙烷
33.1g 碳酸鉀
86.4g 2-丁酮
條件:於86℃下19.3小時及於70℃下50小時
1H NMR(CDCl3,400MHz):δ(1H)=7.40(t,1H),6.80(dd,1H),6.77(m,2H),6.70(dd,1H),4.40(dd,1H),3.95(dd,1H),3.35(m,1H),2.85(dd,1H),2.75(dd,1H),2.65(q,2H),1.25(t,3H)。
實施例1.7 2-{[4-(甲基硫烷基)苯氧基]甲基}環氧乙烷
反應物:15.4g 4-(甲基硫基)酚
45.2g 環氧溴丙烷
36.4g 碳酸鉀
97.1g 2-丁酮
條件:於86℃下16.3小時及於70℃下50.2小時
1H NMR(CDCl3,400MHz):δ(1H)=7.25(AA’BB’,2H),6.88(AA’BB’,2H),4.20(dd,1H),3.90(dd,1H),3.40(m,1H),2.85(dd,1H),2.73(dd,1H),2.40(s,3H)。
用於製備(甲基)丙烯酸-環氧乙烷加合物之一般方法(實施例2.1-2.11)
該環氧乙烷、該催化劑、穩定劑及該(甲基)丙烯酸初始裝入一配備有精密玻璃攪拌器與攪拌器馬達、還有一乾燥管之三頸燒瓶中。將該混合物加熱至90℃,及於這溫度下連續攪拌直到,在
該1H NMR光譜中,顯見該環氧乙烷基團之轉換率為>95%或不再檢測到任何環氧乙烷基團。(MC=主成分(main components),SC=次要成分(secondary component))
實施例2.1+2.2 丙烯酸2-羥基-3-苯氧基丙基酯與丙烯酸1-羥基-3-苯氧基丙烷-2-基(propan-2-yl)酯(約85:15)之混合物
反應物:75.3g苯基縮水甘油醚(Denacol EX141)
328mg 三苯基膦
36.0g 丙烯酸
1.1mg 紫羅蘭醇
條件:反應時間37小時
獲得一澄清、無色、黏性液體。
1H NMR(CDCl3,400MHz):δ(1H)=7.23-7.32(m,2H),6.92-7.00(m,1H),6.84-6.92(m,2H),6.46(d,1H),6.16(dd,1H),5.97(d,1H),5.28(p,1H來自SC),3.9-4.45(m,5H),2.72(t,1H來自SC,OH),2.60(s,寬廣,1H,OH)。
實施例2.3 甲基丙烯酸2-羥基-3-苯氧基丙基酯與甲基丙烯酸1-羥基-3-苯氧基丙烷-2-基酯(約85:15)之混合物
反應物:37.7g苯基縮水甘油醚(Denacol EX141)
164mg 三苯基膦
21.5g 甲基丙烯酸
0.6mg 紫羅蘭醇
條件:反應時間34.5小時
獲得一澄清、無色、黏性液體。
1H NMR(CDCl3,400MHz):δ(1H)=7.25-7.32(m,2H),6.96(t,1H),6.91(d,2H),6.14(s,1H),5.60(s,1H),5.28(p,1H來自SC),3.35(m,2H來自MC),4.29(p,1H來自MC),4.20(d,2H來自SC),4.0-4.1(m,2H來自MC),3.94(m,2H來自SC),2.69(s,寬廣,1H,OH),1.95(s,3H)。
實施例2.4 丙烯酸2-羥基-3-(2-甲基苯氧基)丙
基酯與丙烯酸1-羥基-3-(2-甲基苯氧基)丙烷-2-基酯(約85:15)之混合物
反應物:16.4g 2-[(2-甲基苯氧基)甲基]環氧乙烷
66mg 三苯基膦
7.2g 丙烯酸
11.8mg 紫羅蘭醇
條件:反應時間17小時
獲得一澄清、無色、黏性液體。
1H NMR(CDCl3,400MHz):δ(1H)=7.1-7.2(m,2H),6.88(t,1H),6.80(d,1H),6.44(d,1H),6.18(dd,1H),5.88(d,1H),5.32(p,1H來自SC),4.35-4.45(m,2H來自MC),4.29(p,1H來自MC),4.19(d,2H來自SC),4.0-4.1(m,2H來自MC),3.96(m,2H來自SC),2.93(s,寬廣,1H,OH),2.22(s,3H來自MC),2.20(s,3H,來自SC)。
實施例2.5 丙烯酸2-羥基-3-(3-甲基苯氧基)丙基酯與丙烯酸1-羥基-3-(3-甲基苯氧基)丙烷-2-基酯(約85:15)之混合物
反應物:16.5g 實施例1.5
66mg 三苯基膦
7.3g 丙烯酸
11.9mg 紫羅蘭醇
條件:反應時間17小時
獲得一澄清、無色、黏性液體。
1H NMR(CDCl3,400MHz):δ(1H)=7.13-7.20(t,1H),6.78(d,1H),6.68-6.75(m,2H),6.45(d,1H),6.18(dd,1H),5.87(d,1H),5.28(p,1H來自SC),4.3-4.4(m,2H來自MC),4.28(p,1H來自MC),4.15-4.25(m,2H來自SC),3.98-4.08(m,2H來自MC),3.94(m,2H來自SC),2.90(s,寬廣,1H,OH),2.30(s,3H)。
實施例2.6 丙烯酸2-羥基-3-(3-乙基苯氧基)丙基酯與丙烯酸1-羥基-3-(3-乙基苯氧基)丙烷-2-基酯(約85:15)之混合物
反應物:15.3g 實施例1.6
56mg 三苯基膦
6.2g 丙烯酸
10.8mg 紫羅蘭醇
條件:反應時間17小時
獲得一澄清、無色、黏性液體。
1H NMR(CDCl3,400MHz):δ(1H)=7.13-7.20(m,1H),6.80(d,1H),6.75(s,1H),6.71(dd,1H),6.45(d,1H),6.18(dd,1H),5.85(d,1H),5.28(p,1H來自SC),4.3-4.4(m,2H來自MC),4.25(p,1H來自MC),4.19(d,2H來自SC),3.99-4.07(m,2H來自MC),3.93(d,2H來自SC),3.35(s,寬廣,1H,OH),2.60(q,2H),1.21(t,3H)。
實施例2.7 丙烯酸2-羥基-3-[4-(甲基硫烷基)苯氧基]丙基酯與丙烯酸1-羥基-3-[4-(甲基硫烷基)苯氧基]丙烷-2-基酯(約85:15)之混合物
反應物:35.7g 實施例1.7
119mg 三苯基膦
13.1g 丙烯酸
24.4mg 紫羅蘭醇
條件:於70℃下反應時間39小時
GC-MS(EI)滯留時間(得自乙腈溶液,在提及的GC中,相對於主成分,顯見只全部次要成分>10%):
1. 100%:17.59分鐘(MS-EI:m/e=55,125,129,140,268):異構性主產物(M=268)
2. 17.8%:3.03分鐘(MS-EI:m/e=27,45,55,72):丙烯酸(M=72)
3. 11.2%:21.30分鐘(MS-EI:m/e=55,57,115,129,353,382):丙烯酸3-({4-[3-(丙烯醯基氧基)-2-羥基丙氧基]苯基}硫烷基)-2-羥基丙基酯(M=382)
實施例2.8 丙烯酸3-(聯苯基-2-基氧基)-2-羥基丙基酯與丙烯酸1-(聯苯基-2-基氧基)-3-羥基丙烷-2-基酯(約85:15)
之混合物
反應物:191.2g 2-[(聯苯基-2-基氧基)甲基]環氧乙烷(Denacol EX 142)
0.525g 三苯基膦
57.6g 丙烯酸
2.5mg 紫羅蘭醇
條件:於90℃下反應時間24.5小時
獲得一澄清、無色、黏性液體。
1H NMR(CDCl3,400MHz):δ(1H)=7.45(d,2H),7.38(t,2H),7.2-7.35(m,3H),7.15(t,2H),6.96(d,2H),6.37(dd,1H),6.13(dd,1H),5.81(d,1H),5.28(p,1H來自SC),4.37(t,1H來自SC,OH),4.28-4.35(m,2H),4.15(m,2H來自MC),4.13(p,1H),3.95-4.06(m,2H),3.75(m,2H來自SC),2.74(s,寬廣,1H,OH)。
GC-MS 1.1%丙烯酸,7.8% 2-[(聯苯基-2-基氧基)甲基]環氧乙烷(反應物),1.5%反應物+HCl,2.7%反應物+H2O,73.2%產物(異構物),2.2%產物+丙烯酸,2.7%反應物+聯苯基酚,3.3%產物+反應物
實施例2.9 丙烯酸2-羥基-3-(1-萘基氧基)丙基酯與丙烯酸1-羥基-3-(1-萘基氧基)丙烷-2-基酯(約85:15)之混合物
反應物:46.0g 2-[(1-萘基氧基)甲基]環氧乙烷
0.151g 三苯基膦
16.6g 丙烯酸
0.6mg 紫羅蘭醇
條件:反應時間22.7小時
獲得一澄清、無色、黏性液體。
1H NMR(CDCl3,400MHz):δ(1H)=8.18-8.25(m,1H),7.73-7.80(m,1H),7.38-7.49(m,3H),7.29-7.35(2x t,1H),6.76(d,1H),6.44(2x d,1H),6.15(2x dd,1H),5.82(d,1H),5.43(p,1H來自SC),4.35-4.50(m,3H來自MC),4.30(d,2H來自SC),4.13-4.18(m,2H
來自MC),3.98(d,2H來自SC),3.32(s,寬廣,1H,OH),2.70(t,1H來自SC,OH)。
實施例2.10 丙烯酸2-羥基-3-(2-甲氧基苯氧基)丙基酯與丙烯酸1-羥基-3-(2-甲氧基苯氧基)丙烷-2-基酯(約85:15)之混合物
反應物:10.8g 1,2-環氧基-3-(2-甲氧基苯氧基)丙烷
0.039g 三苯基膦
4.3g 丙烯酸
7.6mg 紫羅蘭醇
條件:反應時間29.3小時
獲得一澄清、無色、黏性液體。
1H NMR(CDCl3,400MHz):δ(1H)=6.82-7.01(m,4H),6.44(2x d,1H),6.15(2x dd,1H),5.82(d,1H),5.28(p,1H來自SC),4.30-4.42(m,2H來自MC),4.27(m,1H來自MC),4.12(dd,1H來自MC,ABX),4.04(dd,1H來自MC,ABX),3.98(d,2H來自SC),3.78-3.85(m,3H,O-Me來自MC與來自SC+2H來自SC),3.21(s,寬廣,1H,OH)。
實施例2.11 丙烯酸2-羥基-3-苯氧基丙基酯
反應物:8.3g 苯基縮水甘油醚
0.030g 1,2-環己胺基-N,N’-雙(3,5-二-t-丁基亞柳基)鈷(III)p-甲苯磺酸鹽單水合物
3.9g 丙烯酸
0.1mg 紫羅蘭醇
條件:於室溫下反應時間40小時
處理:5g的粗產物以25g的乙酸丁酯與甲苯之混合物稀釋及接著藉由重力管柱之方式釋出該鈷催化劑及,添加0.005mg的紫羅蘭醇,於一旋轉蒸發器中釋出該溶劑混合物。
1H NMR(CDCl3,400MHz):δ(1H)=7.28(m,2H),6.98(tt,1H),6.92(dd,2H),6.46(dd,1H),6.17(dd,1H),5.87(dd,
1H),4.32-4.42(m,2H),4.28(m,1H),4.00-4.09(m,2H),2.65(d,1H,OH)。由NMR之純度>92%.
用於製備本發明芳香族二醇醚寫入單體之一般方法(實施例3.1-3.11)
將前驅物(實施例2.1-2.11)、二月桂酸二丁基錫鹽與2,6-二-第三丁基-4-甲基酚初始裝入一配備有精密玻璃攪拌器與攪拌器馬達、氣體入口及乾燥管之三頸燒瓶中。接著,將該混合物加熱至60℃,緩慢地通過空氣,及在約半小時內逐滴添加(甲基)丙烯酸2-異氰酸基乙基酯同時攪拌。連續攪拌直到在該IR光譜中不再可以觀察到任何NCO鍵(2261cm-1)。表1顯示本發明寫入單體之反應條件及特徵之詳細內容:
實施例3.1
實施例3.2
實施例3.3
實施例3.4
實施例3.5
實施例3.6
實施例3.7
實施例3.8
實施例3.9
實施例3.10
實施例3.11
比較例C1:磷硫醯基(phosphorothioyl)參(氧基苯-4,1-二基胺甲醯基氧基乙烷-2,1-二基)參丙烯酸酯[1072455-04-9]
一500mL圓底燒瓶初始裝有0.1g的2,6-二-第三-丁基-4-甲基酚、0.05g的二月桂酸二丁基錫鹽與213.07g的參(p-異氰酸基苯基)硫基磷酸鹽於乙酸乙酯之27%溶液,將其加熱至60℃。接著,逐滴添加42.37g的丙烯酸2-羥基乙基酯及使該混合物仍維持於60℃直到該異氰酸酯含量已下降至低於0.1%。此接著使冷卻及在減壓下完全移除乙酸乙酯。獲得呈一半晶質固體之產物。所獲得的產物具有一nD 20=1.5430(589nm)。
比較例C2:苯-1,3-二基雙[氧基-3-(聯苯基-4-基氧基)丙烷-1,2-二基]雙丙烯酸酯
比較例2在第一階段中由一二硫醇與一環氧乙烷製備(亦參照WO 2012/020061 A1中之實施例4a+b)。
將該環氧乙烷及該催化劑初始裝入一配備有精密玻璃攪拌器與攪拌器馬達、還有一乾燥管之三頸燒瓶中。將該混合物加熱至60至80℃及之後逐滴添加二硫醇。接著,於該指定溫度下連續攪拌直到,在該1H NMR光譜中,顯見該環氧乙烷基團之轉換率為>95%
或不再檢測到任何環氧乙烷基團。
階段1 3,3'-(丁烷-2,3-二基二硫烷二基)雙[1-(聯苯基-2-基氧基)丙烷-2-醇]
反應物:14.3g 2-[(聯苯基-2-基氧基)甲基]環氧乙烷(Denacol EX 142)
36mg 溴化1-丁基-3-甲基咪唑
3.7g 2,3-丁烷二硫醇
條件:在逐滴添加之反應溫度60℃、80℃下,反應時間48.5小時
獲得一澄清、無色、黏性液體。
1H NMR(CDCl3,400MHz):δ(1H)=7.45(d,2H),7.38(t,2H),7.32(m,3H),7.16(t,1H),6.97(d,1H),4.05(d,2H),3.95(m,1H),2.65(dd,1H),2.58(dd,1H),2.4-2.55(m,2H),1.5-1.65(m,2H)
階段2:6,13-雙[(聯苯基-2-基氧基)甲基]-9,10-二甲基-4,15,20-三氧代(trioxo)-5,14,19-三氧雜(trioxa)-8,11-二噻(dithia)-3,16-二氮雜二十二碳-21-烯-1-基丙烯酸酯
階段1,將二月桂酸二丁基錫鹽與2,6-二-第三-丁基-4-甲基酚初始裝入一配備有精密玻璃攪拌器與攪拌器馬達、氣體入口及乾燥管之三頸燒瓶中。接著,將該混合物加熱至60℃,緩慢地通過空氣,及於約半小時內逐滴添加丙烯酸2-異氰酸基乙基酯。連續攪拌直到在該IR光譜中不再可以觀察到任何NCO鍵(2261cm-1)。
反應物:18.0g 產物來自階段1
8.5g 丙烯酸2-異氰酸基乙基酯
13mg 二月桂酸二丁基錫鹽
3mg 2,6-二-第三-丁基-4-甲基酚
條件:於60℃下以35分鐘逐滴添加(放熱式!),之後於60℃下反應時間為16小時
獲得一高黏度的澄清、幾乎無色產物。
n20;D 1.5840(589nm)
比較例C3-C5:
類似於WO 2012/020061A1之比較例3,製造比較例4-6,及測量其黏度。該結果示於表2。
多元醇成分:
一1升燒瓶初始裝有0.18g的Addocat® SO、374.8g的ε-己內酯與374.8g的二官能性聚四氫呋喃聚醚醇(當量重650g/mol OH),將其加熱至120℃及維持於這溫度直到該固體含量(非揮發性組分之比例)為99.5重量%或更高。接著,冷卻該混合物及獲得一呈蠟狀固體之產物。
胺基甲酸酯丙烯酸酯1:2-({[3-(甲基硫烷基)苯基]胺甲醯基}氧基)乙基丙-2-烯酸酯
一100ml圓底燒瓶初始裝有0.02g的2,6-二-第三-丁基-4-甲基酚、0.01g的Desmorapid® Z、11.7g的3-(甲基硫基)苯基異氰酸酯,及將該混合物加熱至60℃。接著,逐滴添加8.2g的丙烯酸2-羥基乙基酯及將該混合物仍維持於60℃直到該異氰酸酯含量已
下降至低於0.1%。此接著冷卻。獲得一呈無色液體之產物。
氟化的胺基甲酸酯:雙(2,2,3,3,4,4,5,5,6,6,7,7-十二氟庚基)-(2,2,4-三甲基己烷-1,6-二基)雙胺甲酸酯
一6升圓底燒瓶初始裝有0.50g的Desmorapid Z與1200g的三甲基六亞甲基二異氰酸酯,及將該混合物加熱至80℃。接著,逐滴添加3798g的1H,1H,7H-全氟庚-1-醇及將該混合物仍維持於80℃直到該異氰酸酯含量已下降至低於0.1%。此接著冷卻。獲得一呈無色油物之產物。
本發明及非本發明介質(試樣)之製造(實施例4.1-4.11及比較例C4.1-C4.5)
將2.940g的上述多元醇成分與2.000g的各個寫入單體(實施例3.1-3.11與比較例C4.1-C4.5)、2.000g的上述胺基甲酸酯丙烯酸酯1、2.000g的上述氟化的胺基甲酸酯、0.15g的CGI 909、15mg的結晶紫、15mg的Irgacure 250、15mg的大小9.18μm之玻璃珠及0.517g的N-乙基吡咯啶酮混合,以使獲得一澄清(在某些情況下稍微霧狀)溶液。此接著冷卻至30℃,摻合545mg的Desmodur® N 3900及重新混合。最後此接著摻合6mg的Fomrez UL 28及重新短暫混合。該產生的液體混合物之後被施用至一載玻片上(得自Corning,NY 14831,USA,Micro載玻片平面:厚度0.96至1.06mm,75mm x 50mm,類型:2947-75x50)及以第二載玻片覆蓋其上。將這試驗樣品於室溫下儲存12小時及在這程序中被固化。接著,利用阻隔光線將該介質包裝。
本發明及非本發明介質之物理數據測定
全像性質DE及△n之測量係藉以上在該「試驗方法」段落中所述方法進行。
霧度之測量同樣係藉以上在該「試驗方法」段落中所述方法進行,除了該測量係藉初始於室溫下周圍環境光線(ambient light)中使各個介質脫色(bleaching)約15至30分鐘直到該顏色不再視覺上可察覺到之外。
該測量結果示於表3。
由表3顯見,由包含式(1)之寫入單體之本發明配製物構成的全像介質對於△n>0.02的透射全像圖而言展現了顯著的或較好的全像性能。再者,本發明實施例適用於製造低霧度全像介質及於層厚度大於6μm,展現一低於5%之霧度。在本發明實施例4.1-4.11中,在沒有添加溶劑下,該寫入單體在遠低於5分鐘之內快速且容易溶解,反觀比較例C1-C5之寫入單體則花費更長時間來完全溶解。因此,在比較例中該光聚合物配製物之製造會花費更多時間。
M:鏡子
S:快門
SF:空間濾光器
CL:準直儀透鏡
PBS:偏振敏感性光束分離器
D:檢測器
I:虹膜式光圈
RD:轉盤參考方向
Claims (31)
- 根據申請專利範圍第1項之光聚合物配製物,其特徵在於在芳香族系統中該芳基基包含5至21個碳原子及/或雜原子。
- 根據申請專利範圍第1項之光聚合物配製物,其特徵在於在芳香族系統中該芳基基包含5至18個碳原子及/或雜原子。
- 根據申請專利範圍第1項之光聚合物配製物,其特徵在於在芳香族系統中該芳基基包含6至16個碳原子及/或雜原子。
- 根據申請專利範圍第1項之光聚合物配製物,其特徵在於在芳香 族系統中該芳基基包含6至12個碳原子及/或雜原子。
- 根據申請專利範圍第1項之光聚合物配製物,其特徵在於在芳香族系統中該芳基基包含6至10個碳原子及/或雜原子。
- 根據申請專利範圍第1及2項中任一項之光聚合物配製物,其特徵在於該芳基基經選自下述組群之1至5個相同或不同取代基所取代:正烷基、分支的烷基、烷氧基、苯基、苄基、苯基烷基、萘基、甲基硫基(methylthiyl)、乙基硫基(ethylthiyl)、烷基硫基(alkylthiyl)、烷基硫基烷基、苯氧基、苯基硫基(phenylthiyl)、萘基硫基(napthylthiyl)、氟、氯、溴及/或碘。
- 根據申請專利範圍第1及2項中任一項之光聚合物配製物,其特徵在於該芳基基經選自下述組群之1至3個相同或不同取代基所取代:正烷基、分支的烷基、烷氧基、苯基、苄基、苯基烷基、萘基、甲基硫基(methylthiyl)、乙基硫基(ethylthiyl)、烷基硫基(alkylthiyl)、烷基硫基烷基、苯氧基、苯基硫基(phenylthiyl)、萘基硫基(napthylthiyl)、氟、氯、溴及/或碘。
- 根據申請專利範圍第1及2項中任一項之光聚合物配製物,其特徵在於該芳基基經選自下述組群之1至3個相同或不同取代基所取代:甲基、乙基、硫基甲基、甲氧基、苯基。
- 根據申請專利範圍第1項之光聚合物配製物,其特徵在於該芳基基為選自苯基、甲基苯基、乙基苯基、硫基甲基苯基、甲氧基苯基、聯苯基及萘基之組群。
- 根據申請專利範圍第1及2項中任一項之光聚合物配製物,其特徵在於R3為一基,選自-CH2-、-CH2CH2-、-CH(CH3)CH2-、-CH2CH(CH3)-、-CH2CH2CH2-、-CH2CH2CH2CH2-、-CH2CHOCH2CH2-、-CH2CH2OCH2CH2OCH2CH2-之組群。
- 根據申請專利範圍第1及2項中任一項之光聚合物配製物,其特徵在於R3為一基,選自-CH2CH2-、-CH(CH3)CH2-、-CH2CH(CH3)-、-CH2CH2CH2CH2-之組群。
- 根據申請專利範圍第1及2項中任一項之光聚合物配製物,其特徵在於R3為-CH2CH2-。
- 根據申請專利範圍第1及2項中任一項之光聚合物配製物,其特徵在於該R1基為一式(II)之基及該R2基為一式(III)之基,式中R3基為-CH2CH2-基。
- 根據申請專利範圍第1及2項中任一項之光聚合物配製物,其特徵在於該R1基為一式(III)之基及該R2基為一式(II)之基,式中R3基為-CH2CH2-基。
- 根據申請專利範圍第1及2項中任一項之光聚合物配製物,其特徵在於該基質聚合物B)係經交聯。
- 根據申請專利範圍第1及2項中任一項之光聚合物配製物,其特徵在於該基質聚合物為聚胺基甲酸酯類。
- 根據申請專利範圍第17項之光聚合物配製物,其特徵在於該基質聚合物為以聚酯C4聚醚多元醇類為基底的聚胺基甲酸酯類。
- 根據申請專利範圍第1及2項中任一項之光聚合物配製物,其特徵在於另外包含單體的氟胺基甲酸酯類。
- 一種全像介質,包含根據申請專利範圍第1至22項中任一項之光聚合物配製物,或可使用根據申請專利範圍第1至22項中任一項之光聚合物配製物獲得。
- 根據申請專利範圍第23項之全像介質,一全像圖已曝光至其內。
- 根據申請專利範圍第24項之全像介質,其特徵在於該全像圖為一反射、透射、同軸、離軸、全孔轉移、白光透射、Denisyuk、離軸反射或邊緣光全像圖,或者是一全像立體圖。
- 根據申請專利範圍第25項之全像介質,其特徵在於該全像圖為一反射、透射或邊緣光全像圖。
- 一種視覺顯示器,包含一根據申請專利範圍第24至26項中任一項之全像介質。
- 一種申請專利範圍第24至26項中任一項之全像介質之用途,用於晶片卡、身分證件、3D影像、產品保護標籤、標籤、鈔票、全像光學元件之製造。
- 如申請專利範圍第28項之全像介質之用途,係用於視覺顯示器之 全像光學元件之製造。
- 根據申請專利範圍第30項之芳香族二醇醚,其特徵在於芳基為一基選自甲基苯基、乙基苯基、硫基甲基苯基、甲氧基苯基、聯苯基及萘基之組群,及/或在各情況下該R1及R2基之一者為一式(II)之基及在各情況下該R1及R2基之一者為一式(III)之基,式中R3為-CH2CH2-基。
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