TWI702245B - 黏性環氧漿料之製造方法及由其得到之環氧漿料 - Google Patents
黏性環氧漿料之製造方法及由其得到之環氧漿料 Download PDFInfo
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- TWI702245B TWI702245B TW105115420A TW105115420A TWI702245B TW I702245 B TWI702245 B TW I702245B TW 105115420 A TW105115420 A TW 105115420A TW 105115420 A TW105115420 A TW 105115420A TW I702245 B TWI702245 B TW I702245B
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- epoxy
- viscosity
- slurry
- epoxy slurry
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Abstract
一種由至少一種液態多官能基環氧化物所形成的黏性環氧漿料之製造方法，其包括以下步驟：- 在至少一種液態多官能基環氧化物中加入起始劑，該起始劑係自包含下列之群組中所選出：缺電子的單異氰酸酯、光起始劑與熱起始劑；- 將組成物混合；- 將多官能基環氧化物聚合，使所產生的環氧漿料的黏度為所使用的環氧化物在未轉化狀態下之黏度的至少兩倍高，較佳為至少四倍高，特別是至少十倍高；如此能製造出具壓敏黏著性質之環氧黏著劑。
Description
本發明係關於一種由至少一種液態多官能基環氧化物所形成的黏性環氧漿料之製造方法、一種依照該方法所得到的黏性環氧漿料、一種具此種環氧漿料之黏著劑以及膠帶、及此種環氧漿料、此種黏著劑獲此種膠帶之用途，其中該製造方法係包括以下步驟：在至少一種液態多官能基環氧化物中加入起始劑並將多官能基環氧化物加以聚合，該起始劑係自包含下列之群組中所選出：缺電子的單異氰酸酯、光起始劑與熱起始劑。
具壓敏黏著性質的環氧黏著劑能透過添加基質聚合物來製作。黏著強度經常是隨著環氧化物量增加而升高。大多數環氧化物係使用於液態黏著劑，由於其具相對低的黏度及高環氧基含量，因此不會添加於壓敏黏著性膠帶。為了得到壓敏黏著性膠帶需要高黏度或固態的環氧化物。
典型上環氧氯丙烷系環氧樹脂的黏度係透過環氧氯丙烷的比例及消耗環氧基濃度所產生的分子量提升來調整[“Epoxy Adhesive Formulations”2006,E.M.
Petrie,S.30ff]。一些例子，如(甲酚)酚醛環氧化物，係透過另外的合成途徑製成，並帶有環氧基作為側基，因此分子量的增加不會導致環氧基濃度下降。
然而，除了上述酚醛環氧化物以及以環氧氯丙烷製造的寡聚物以外，沒有其他方法來得到高黏度的環氧化物，特別是除了上述以外的環氧化物。
特定的環氧單體，如環氧環己基衍生物，其不是透過環氧氯丙烷途徑製造，因而大多極具流動性(例如Uvacure 1500)。由於許多用於交聯反應的環氧化物(其每分子含有一個以上環氧基)其不能簡單地以聚合來提升黏度，因為其會立即交聯並形成不溶性的沉澱。因此這些環氧環己基單體被較佳地使用於陽離子性固化黏著劑中，特別是透過對光不穩定的產酸劑來用於UV引發的硬化。
因此需要一種方法用來提升不是透過環氧氯丙烷途徑所得到的環氧化物之黏度。
AU 758128 B2敘述此種具儲藏穩定性的陽離子型固化之多官能基環氧摻合物。為了達到多官能基環氧樹脂的儲藏穩定性，依照此文獻需要避免不期望的過早的聚合。這件事係藉由在聚合多官能基環氧化物單體時添加0.0005至10重量%的有機及/或無機的鹼土金屬或鹼金屬化合物來達成。因此無論如何在期望的交聯前應避免聚合。除了這些黏著劑創新的穩定以外，依照此文獻，陽離子型固化的液態黏著劑特佳為環氧環己基衍生物，其期望能以此單體製造出高黏度環氧化物。
SG 160949 B建議讓二環氧化物與二異氰酸酯反應。由此混合物形成具有Mw<3,000g/mol及低分散性之環狀三聚物(三聚異氰酸酯)及
唑啶酮，其之後可如環氧化物固化。此需要至少使用至少雙官能基的物質，因為不然的話就沒有反應基用於之後的固化了。然而所得到的化合物具有低黏度。
因此，本發明之課題為提供一種方法，其能夠由原本液態的環氧化物製造出具目標黏度之黏著劑。該產物應可溶於溶劑中，並可藉由升溫熔化。
此課題的解答係藉由開頭所提到的形式之方法，其中組成物先混合，接下來進行多官能基環氧化物之聚合，使所產生的環氧漿料的黏度，為所使用的環氧化物在未轉化狀態下之黏度的至少兩倍高，較佳為至少四倍高，特別是至少十倍高。其中環氧化物係以產生高分子量聚環氧化物(從例如雙環氧單體)而不使其交聯的方式來初步聚合。如此產生的環氧漿料特別適合用來製造具有壓敏黏著性質的環氧黏著劑。其中重要的是，只有在起始劑均勻分散於環氧化物中後才進行起始作用。否則反應中心會太靠近彼此並產生交聯，這是在這個階段所不期望的。為了達成混合，能例如加以攪拌，但也可想到其他可行形式的混合。
只要沒有另外說明，所有在本申請案中所提出的黏度數據係基於在23℃依據DIN 53019-1所做的量測。
其中「環氧漿料」係指黏度達至少1Pa．s(等於1,000mPa．s)之環氧化物。
第1圖顯示經過不同長度的時間區間聚合的Uvacure漿料之分子量分布。
第2圖顯示，即使在80℃幾乎不再進行進一步的聚合，然而沒添加起始劑捕捉劑仍然劇烈地進行聚合。
特佳為本發明之方法係進行至使在所產生的環氧漿料中，還存在至少65%、較佳為至少75%、特別是至少80%的原始環氧基。因此在漿料中大部分的環氧單元還是以單體形態存在。相應地，當在所產生的環氧漿料中含有高分子量未交聯之聚環氧化物時係更佳的。若環氧漿料中大量所使用的多官能基環氧單體仍未反應地以單體存在，並僅孤立地形成高分子量但仍未交聯的聚環氧化物，係特別有助益的。
雙環氧化物特別適合作為多官能基環氧化物。在進行聚合後，其能使用另一個環氧基在之後於環氧黏著樹脂中用來交聯。
作為多官能基環氧化物，已證實特佳其中為雙(環氧基環己基)衍生物(特別是3,4-環氧環己甲酸3,4-環氧環己甲酯)與基於雙酚A、雙酚S或雙酚F之雙環氧化物。以這些環氧化物能製作出黏度很適合把環氧化物進一步加工為壓敏黏著性環氧化物之漿料。
在起始劑係自包含光起始劑與熱起始劑之群組中所選出，且使用的量為最高0.1重量%，較佳為最高0.08重量%，特佳為最高0.05重量%時，本發明之方法能特佳地實施。藉此能以特別容易且易於操作的方式達到尋求的黏度。
除了這些用於陽離子型環氧化物固化的典型起始劑以外，令人意外地特定的異氰酸酯也特別適合作為用於本發明之起始劑。
作為起始劑，係以缺電子的單異氰酸酯特別適合，其係以最高10重量%的量使用，較佳為最高8重量%，特別是最高7重量%。在使用的單異氰酸酯的量在7±0.5重量%時，能特別良好地控制反應。適合的單異氰酸酯係特別自包含以下之群組中選出：異氰酸對甲苯酯、異氰酸鄰甲苯酯與磺醯異氰酸酯，磺醯異氰酸酯特別為異氰酸對甲苯磺醯甲酯、異氰酸鄰甲苯磺醯甲酯、4-氯苯甲基磺醯異氰酸酯、鄰甲苯磺醯異氰酸酯、對甲苯磺醯異氰酸酯與苯甲基磺醯異氰酸酯，其中特佳為對甲苯磺醯異氰酸酯。
作為實施方法的溫度範圍，已證實特佳範圍係介於20與120℃，較佳為介於40與100℃，特別是介於80與90℃。
其中溫度與起始劑量有一相互關係。添加的起始劑越多，要達到相同的反應速度之溫度可以越低。在例如缺電子的異氰酸酯之情形，於室溫下10重量%的起始劑僅達到緩慢的速度，而於85℃以7重量%的起始劑量在數小時內就足以完成反應。
此外，較佳為在達到所期望的黏度時藉由添加起始劑捕捉劑來中止聚合。藉此能使所得到的環氧漿料穩定儲藏。即使在例如80℃之較高的溫度下，所得到的環氧漿料也能穩定儲藏超過數月。作為起始劑捕捉劑，特別適合由水與丙酮所組成之混合液、鹼(土)金屬氫氧化物之溶液、或鹼(土)金屬烷氧化物之溶液。在使用由水與丙酮所組成之混合液的情形，兩種成分的比例特佳為1：1。
起始劑捕捉劑的量較佳應相當於或是實質上等同於起始劑的量。即，在使用7g的起始劑時，較佳也使用7g的起始劑捕捉劑。
此外，本發明之方法特佳為多官能基環氧化物之聚合係進行至使所產生的環氧漿料所具有的多分散性D為至少3，較佳為至少5，特別是至少8。其中多分散性不是藉由像混合不同的聚合物而得，而是基於反應條件形成完全不同大小的聚合物分子。多分散性D為分子量分布的評價方法。多分散性D係定義為所存在的聚合物之重量平均分子量Mw/數量平均分子量Mn。因此多分散性的值大，表示從極短鏈至長鏈的巨分子之寬的分子量分布，即，在聚合物中存在許多不同鏈長度的分子。
對於本發明來說這表示，單、雙或多峰的分子量分布，係以能找到從低分子量組成成分(<2,000g/mol)一直到極高分子量的組成成分(>300,000g/mol)的分子的方式所形成。
此分子量分布的特徵特別有助於本發明產物的高環氧含量(許多低分子量的雙環氧化物)且同時具高黏性特性(極高分子量的環氧化物)之較佳性質。
令人驚訝地發現，本發明之方法會導致在聚合期間黏度的緩慢上升。黏度上升係歸因於極高分子量的聚環氧化物之形成。雖然其為會極快的形成不溶性的高度交聯網絡之多官能基(特別是雙官能基)的環氧化物，但以此方法所製成的環氧黏著樹脂仍保持可溶性。此性質的解釋是，藉由起始劑(如異氰酸對甲苯磺醯甲酯)所形成的起始物種相對少量，因此成長鏈不會相遇，因而在極低的環氧化物轉化率下形成少量極高分子量的聚合物。GPC測量與FT-IR光譜支持此理論。其中重要的是，起始劑係在均勻分散於環氧化物中後才開始起始作用，因此在此階段不會發生交聯。
此外，本發明關於一種依據本發明之方法所製得的黏性環氧漿料。本發明更進一步關於一種黏性環氧漿料，其包含多官能基環氧單體與由其所產生的高分子量未交聯之多官能基聚環氧化物，其中該環氧漿料的黏度係所使用的環氧化物在未轉化之狀態下的黏度的至少兩倍高，較佳為至少四倍高，特別是至少十倍高。
其中較佳為在環氧漿料中所包含的聚環氧化物之分子量分布含括至少2,000g/mol至300,000g/mol之範圍。這表示，在環氧漿料中存在具極不同的分子量(從很低到極高)之環氧化物分子，其中包含從低分子量(<2,000g/mol)一直到高分子量(>300,000g/mol)的所有化合物。其也可包含更低或更高分子量之化合物。
較佳為本發明之環氧漿料於25℃儲存下每日的黏度上升係小於5Pa．s。藉此有充分的儲存穩定性，而能讓環氧漿料在使用前存放更長期間。
特佳的黏性環氧漿料為其中環氧單體為3,4-環氧環己甲酸3,4-環氧環己甲酯，且黏度達至少1Pa．s(1,000mPa．s)，較佳為10Pa．s(10,000mPa．s)，特別是25Pa．s(25,000mPa．s)。
本發明還關於一種水氣阻隔性黏著劑，其含有由至少一種本發明之環氧漿料、至少一種彈性體、任選的溶劑所構成的黏著劑基質，其中該黏著劑基質在反應性樹脂組成物活化後所具有的水氣滲透率係小於100g/m2d，較佳為小於60g/m2d，特別是小於30g/m2d。對於此種水氣阻隔性黏著劑來說，本發明之環氧漿料為特別合適的，因為基於其黏度而能良好的加工，特別是能夠製作具充足的黏度之黏著劑，使所得到的黏著劑能良好的操作並能容易的施用。
此外，本發明還關於一種膠帶，其含有本發明之黏性環氧漿料或是本發明之水氣阻隔性黏著劑。此種膠帶能特別容易地施用。
以其原樣存在的環氧漿料，或是由其所製成的黏著劑，或是由其所製成的膠帶之特別適合的應用領域，係有機電子裝置中的結構之封裝。另外還可想到無數個需要壓敏黏著性的環氧樹脂黏著劑之其他用途。
特佳用於聚合反應的起始劑，如前所述為缺電子的單異氰酸酯，例如：異氰酸對甲苯酯、異氰酸對
甲苯磺醯甲酯、異氰酸鄰甲苯酯或異氰酸鄰甲苯磺醯甲酯。特佳為磺醯異氰酸酯的衍生物(R-SO2-NCO、R-SO2-CH2-NCO)，例如：4-氯苯甲基磺醯異氰酸酯、鄰甲苯磺醯異氰酸酯、對甲苯磺醯異氰酸酯、苯甲基磺醯異氰酸酯。
能據以達到本發明之分子量分布的光起始劑例如但不限於：鋶鹽(參見例如US 4,231,951 A、US 4,256,828 A、US 4,058,401 A、US 4,138,255 A及US 2010/063221 A1)如：六氟砷酸三苯基鋶、六氟硼酸三苯基鋶、三苯基鋶四氟硼酸、肆(五氟苯甲基)硼酸三苯基鋶、四氟硼酸甲基二苯基鋶、肆(五氟苯甲基)硼酸甲基二苯基鋶、六氟磷酸二甲基苯基鋶、六氟磷酸三苯基鋶、六氟銻酸三苯基鋶、六氟砷酸二苯基萘基鋶、六氟磷酸三甲苯基鋶、六氟銻酸甲氧苯基二苯基鋶、四氟硼酸4-丁氧基苯基二苯基鋶、肆(五氟苯甲基)硼酸4-丁氧基苯基二苯基鋶、六氟銻酸4-氯苯基二苯基鋶、六氟磷酸參(4-苯氧基苯基)鋶、六氟砷酸二(4-乙氧基苯基)甲基鋶、四氟硼酸4-乙醯基苯基二苯基鋶、肆(五氟苯甲基)硼酸4-乙醯基苯基二苯基鋶、六氟磷酸參(4-硫甲氧基苯基)鋶、六氟銻酸二(甲氧基磺醯基苯基)甲基鋶、四氟硼酸二(甲氧基萘基)甲基鋶、
肆(五氟苯甲基)硼酸二(甲氧基萘基)甲基鋶、六氟磷酸二(甲氧甲醯基苯基)甲基鋶、肆[3,5-雙(三氟甲基)苯基]硼酸(4-辛氧基苯基)二苯基鋶、肆(五氟苯基)硼酸參[4-(4-乙醯基苯基)硫苯基]鋶、肆[3,5-雙(三氟甲基)苯基]硼酸參(十二烷基苯基)鋶、四氟硼酸4-乙醯胺基苯基二苯基鋶、肆(五氟苯甲基)硼酸4-乙醯胺基苯基二苯基鋶、六氟磷酸二甲基萘基鋶、四氟硼酸三氟甲基二苯基鋶、肆(五氟苯甲基)硼酸三氟甲基二苯基鋶、六氟磷酸苯基甲基苯甲基鋶、六氟磷酸5-甲基噻蒽鎓、六氟磷酸10-苯基-9,9-二甲基硫
鎓、四氟硼酸10-苯基-9-氧硫
鎓、肆(五氟苯甲基)硼酸10-苯基-9-氧硫
鎓、四氟硼酸5-甲基-10-氧噻蒽鎓、肆(五氟苯甲基)硼酸5-甲基-10-氧噻蒽鎓，及六氟磷酸5-甲基-10,10-二氧噻蒽鎓，或對甲苯磺醯異氰酸酯，或錪鹽(參見例如US 3,729,313 A、US 3,741,769 A、US 4,250,053 A、US 4,394,403 A與US 2010/063221 A1)，如：四氟硼酸二苯基錪、四氟硼酸二(4-甲基苯基)錪、四氟硼酸苯基-4-甲基苯基錪、
六氟磷酸二(4-氯苯基)錪、四氟硼酸二萘基錪、四氟硼酸二(4-三氟甲基苯基)錪、六氟磷酸二苯基錪、六氟磷酸二(4-甲基苯基)錪、六氟砷酸二苯基錪、四氟硼酸二(4-苯氧基苯基)錪、六氟磷酸苯基-2-噻吩基錪、六氟磷酸3,5-二甲基吡唑基-4-苯基錪、六氟銻酸二苯基錪、四氟硼酸2,2'-二苯基錪、六氟磷酸二(2,4-二氯苯基)錪、六氟磷酸二(4-溴苯基)錪、六氟磷酸二(4-甲氧基苯基)錪、六氟磷酸二(3-羧基苯基)錪、六氟磷酸二(3-甲氧基羰基苯基)錪、六氟磷酸二(3-甲氧基磺醯基苯基)錪、六氟磷酸二(4-乙醯胺基苯基)錪、六氟磷酸二(2-苯并噻吩基)錪，參(三氟甲基磺醯基)甲基二芳基錪，如：六氟銻酸二苯基錪，肆(五氟苯基)硼酸二芳基錪，如：肆(五氟苯基)硼酸二苯基錪、六氟銻酸(4-正癸氧基苯基)苯基錪、六氟銻酸[4-(2-羥基正十四烷氧基)苯基]苯基錪、三氟磺酸[4-(2-羥基正十四烷氧基)苯基]苯基錪、六氟磷酸[4-(2-羥基正十四烷氧基)苯基]苯基錪、
肆(五氟苯基)硼酸[4-(2-羥基正十四烷氧基)苯基]苯基錪、六氟銻酸雙(4-三級丁基苯基)錪、六氟磷酸雙(4-三級丁基苯基)錪、三氟磺酸雙(4-三級丁基苯基)錪、四氟硼酸雙(4-三級丁基苯基)錪、六氟銻酸雙(十二烷基苯基)錪、四氟硼酸雙(十二烷基苯基)錪、六氟磷酸雙(十二烷基苯基)錪、三氟甲磺酸雙(十二烷基苯基)錪、六氟銻酸二(十二烷基苯基)錪、三氟甲磺酸二(十二烷基苯基)錪、硫酸氫二苯基錪、硫酸氫4,4'-二氯二苯基錪、硫酸氫4,4'-二溴二苯基錪、硫酸氫3,3'-二硝基二苯基錪、硫酸氫4,4'-二甲基二苯基錪、硫酸氫4,4'-雙琥珀醯亞胺基二苯基錪、硫酸氫3-硝基二苯基錪、硫酸氫4,4'-二甲氧基二苯基錪、肆(五氟苯基)硼酸雙(十二烷基苯基)錪、肆[3,5-雙(三氟甲基)苯基]硼酸(4-辛氧基苯基)苯基錪，及肆(五氟苯基)硼酸(甲苯基異丙苯基)錪，或二茂鐵鹽(參見例如EP 542 716 B1)如：η5-(2,4-環戊二烯-1-基)-[(1,2,3,4,5,6,9)-(1-甲基乙基)苯]鐵。
商品化的光起始劑的範例有：Union Carbide公司的Cyracure UVI-6990、Cyracure UVI-6992、Cyracure UVI-6974及Cyracure UVI-6976；Adeka公司的Optomer SP-55、Optomer SP-150、Optomer SP-151、Optomer SP-170及Optomer SP-172；Sanshin Chemical公司的San-Aid SI-45L、San-Aid SI-60L、San-Aid SI-80L、San-Aid SI-100L、San-Aid SI-110L、San-Aid SI-150L及San-Aid SI-180L；Sartomer公司的SarCat CD-1010、SarCat CD-1011及SarCat CD-1012；Degussa公司的Degacure K185；Rhodia公司的Rhodorsil Photoinitiator 2074；Nippon Soda公司的CI-2481、CI-2624、CI-2639、CI-2064、CI-2734、CI-2855、CI-2823及CI-2758；IGM Resins公司的Omnicat 320、Omnicat 430、Omnicat 432、Omnicat 440、Omnicat 445、Omnicat 550、Omnicat 550 BL及Omnicat 650；Daicel公司的Daicat II；Daicel-Cytec公司的UVAC 1591；3M公司的FFC 509；Midori Kagaku公司的BBI-102、BBI-103、BBI-105、BBI-106、BBI-109、BBI-110、BBI-201、BBI、301、BI-105、DPI-105、DPI-106、DPI-109、DPI-201、DTS-102、DTS-103、DTS-105、NDS-103、NDS-105、NDS-155、NDS-159、NDS-165、TPS-102、TPS-103、TPS-105、TPS-106、TPS-109、TPS-1000、MDS-103、MDS-105、MDS-109、MDS-205、MPI-103、、MPI-105、MPI-106、MPI-109、DS-100、DS-101、MBZ-101、MBZ-201、MBZ-301、NAI-100、NAI-101、NAI-105、NAI-106、NAI-109、NAI-1002、NAI-1003、NAI-1004、NB-101、NB-201、NDI-101、
NDI-105、NDI-106、NDI-109、PAI-01、PAI-101、PAI-106、PAI-1001、PI-105、PI-106、PI-109、PYR-100、SI-101、SI-105、SI-106及SI-109；Nippon Kayaku公司的Kayacure PCI-204、Kayacure PCI-205、Kayacure PCI-615、Kayacure PCI-625、Kayarad 220及Kayarad 620、PCI-061T、PCI-062T、PCI-020T、PCI-022T；Sanwa Chemical公司的TS-01及TS-91；Deuteron公司的Deuteron UV 1240；Evonik公司的Tego Photocompound 1465N；GE Bayer Silicones公司的UV 9380 C-D1；Cytec公司的FX 512；Bluestar Silicones公司的Silicolease UV Cata 211；及BASF公司的Irgacure 250、Irgacure 261、Irgacure 270、Irgacure PAG 103、Irgacure PAG 121、Irgacure PAG 203、Irgacure PAG 290、Irgacure CGI 725、Irgacure CGI 1380、Irgacure CGI 1907及Irgacure GSID 26-1。
熟習本技藝者還熟知其他同樣能依據本發明使用之系統。光起始劑係以不組合的形式或以兩種以上光起始劑之組合來使用。
較佳為光起始劑在小於350nm與較佳在大於250nm處具有吸收。在超過350nm吸收的起始劑也能使用於例如紫光範圍。特佳為使用鋶系光起始劑，因為其具有較佳的UV吸收特性。
熱起始劑，所謂的熱酸化劑(「熱產酸劑」TAG)，為例如US 5,242,715 A中所述的帶有例如PF6 -、AsF6 -、或SBF6 -陰離子之苯甲硫醇鎓鹽，「Study of
Polymerization Mechanism and Kinetics of DGEBA with BF3-amine Complexes Using FT-IR and Dynamic DSC」(Ghaemy et al.，Iranian Polymer Journal，Vol.6，No.1,1997)中所述的BF3-胺錯合物，「Study of Lanthanide Triflates as New Curing Initiators for Cycloaliphatic Epoxy Resins」(C.Mas et al.，Macromolecular Chemistry and Physics，2001，202，No.12)中所述的鑭系三氟甲磺酸鹽，或受阻的超強酸，例如：三氟甲磺酸銨；全氟丁磺酸(PFBuS)銨；Ad-TFBS[4-金剛烷羧基-1,1,2,2-四氟丁磺酸]銨；AdOH-TFBS[3-羥基-4-金剛烷羧基-1,1,2,2-四氟丁磺酸]銨；Ad-DFMS[金剛烷基甲氧基羰基)二氟甲磺酸]銨；AdOH-DFMS[3-羥基金剛烷基甲氧基羰基)二氟甲磺酸]銨；DHC-TFBSS[4-脫氫膽酸-1,1,2,2-四氟丁磺酸]銨；與ODOT-DFMS[六氫-4,7-環氧異苯并呋喃-1(3H)-酮,6-(2,2'-二氟-2-磺酸根乙酸酯)]銨。
此種系統可購自例如King Industries的品名TAG-2678、TAG-2713或TAG-2172。此受阻的酸在升溫下釋放出例如三氟甲磺酸、對甲苯磺酸或十二烷基苯磺酸，其起始環氧化物之陽離子固化。
測試方法
黏度量測：
動態黏度為流體塗布材料之流動性的度量方法。動態黏度能依照DIN 53019測定。流體係指黏度小於108Pa．s。黏度係於具標準幾何之圓筒型旋轉黏度計
中，依據DIN 53019-1在23℃的量測溫度與1s-1的剪切速度下測定。
分子量分布：
數量平均分子量Mn與重量平均分子量Mw之分子量測定係以凝膠滲透層析法(GPC)測定。作為溶析液係使用含0.1體積%三氟乙酸的THF(四氫呋喃)。量測係在25℃進行。作為保護管柱，使用PSS-SDV，10μ，ID 8.0mm x 50mm。用來分離係使用管柱PSS-SDV，10μ ID 8.0mm x 300mm。樣本濃度達1.5g/l，流量為每分鐘0.5ml。量測係相對於聚(甲基丙烯酸甲酯)標準品進行。
本說明書中數量平均分子量Mn、重量平均分子量Mw與多分散性的數據係依據凝膠滲透層析法(GPC)之測定或類似方法的評價。
使用材料：
實施例1：以缺電子的單異氰酸酯起始：
於2L玻璃反應器中在氮氣環境下將1kg的Uvacure 1500加熱至85℃。Uvacure 1500的黏度達到0.25Pa．s。在氮氣逆流中加入起始劑並緩慢攪拌溶液。
於反應期間在不同的反應時間後採取樣本並以GPC與黏度計分析來測定黏度。
其中顯示，隨著反應時間增加，多分散性也增加。對於在實施例中所使用的物質來說，在TSI量為7重量%時有反應速度最大值。此時使用更多的起始劑量不會導致更高的反應速度。
從表2也能清楚看出，以較高的起始劑量反應進行的明顯較快，且黏度上升達成的快上許多。
第1圖顯示經過不同長度的時間區間聚合的Uvacure漿料之分子量分布。引人注目的是極寬的分布，其包含許多小於1,000g/mol的分子，還有部分超過106g/mol的長鏈，這些長鏈造成高黏度。
終止反應
在達到期望的黏度後終止反應，此時加入相當於起始劑量之量的水/丙酮混合液(比例1：1)作為起始劑捕捉劑。第2圖顯示，即使在80℃幾乎不再進行進一步的聚合，然而沒添加起始劑捕捉劑仍然劇烈地進行聚合。
實施例2：以高度稀釋的光起始劑起始
於2L玻璃反應器中對1kg的Epon Resin 828在黑暗中且在23℃的氮氣環境下，於攪拌下(50U/Min)加入光起始劑(六氟銻酸三芳基鋶)。反應的起始係藉由以放射狀地設置在聚合反應器周圍的4盞中壓汞燈照射2分鐘來進行。
於反應期間在不同的反應時間後採取樣本並以GPC與黏度計分析來測定黏度。
從中可以看出，需要的起始劑量明顯更少，且黏度在相同的反應時間下也隨著起始劑量的增加而上升。
實施例3：以高度稀釋的熱起始劑起始
對由Uvacure 1500在甲苯中形成的30%溶液加入0.02% TAG-2678，並在回流下加熱。在期望的反應時間後冷卻去活化，並去除溶劑。如在其他實施例中得到完全透明的無色環氧漿料。在1h的反應時間後量測出的黏度就已經是起始物的兩倍大了。
實施例3顯示，用熱起始劑也能在溶液中且無保護氣體下產生黏性環氧漿料。
Claims (27)
- 一種由至少一種液態多官能基環氧化物來製造黏性環氧漿料之方法，其包括以下步驟：- 在至少一種液態多官能基環氧化物中加入起始劑，該起始劑係自包含下列之群組中所選出：缺電子的單異氰酸酯、光起始劑與熱起始劑；- 將組成物混合；及- 將多官能基環氧化物聚合，使所產生的環氧漿料的黏度為所使用的環氧化物在未轉化狀態下之黏度的至少兩倍高；其中所產生的環氧漿料包含未交聯之聚環氧化物。
- 如請求項1之方法，其中所產生的環氧漿料具有重量平均莫耳質量Mw至少5,100g/mol。
- 如請求項2之方法，其中所產生的環氧漿料具有重量平均莫耳質量Mw最高78,400g/mol。
- 如請求項1至3中任一項之方法，其中該未交聯之聚環氧化物具有2,000g/mol至300,000g/mol範圍內的分子量。
- 如請求項1至3中任一項之方法，其中在所產生的環氧漿料中至少65%的原始環氧基還存在。
- 如請求項1至3中任一項之方法，其中該至少一種液態多官能基環氧化物為雙環氧化物。
- 如請求項1至3中任一項之方法，其中該至少一種液態多官能基環氧化物為雙(環氧基環己基)衍生物，或基於雙酚A、雙酚S或雙酚F之雙環氧化物。
- 如請求項1至3中任一項之方法，其中該至少一種液態多官能基環氧化物為3,4-環氧環己甲酸3,4-環氧環己甲酯。
- 如請求項1至3中任一項之方法，其中該起始劑係自包含光起始劑與熱起始劑之群組中所選出，且使用的量為最高0.1重量%。
- 如請求項1至3中任一項之方法，其中該起始劑為缺電子的單異氰酸酯，且使用的量最高為10重量%。
- 如請求項10之方法，其中該起始劑係自包含下列之群組中所選出：異氰酸對甲苯酯、異氰酸鄰甲苯酯與磺醯異氰酸酯。
- 如請求項10之方法，其係在介於20與120℃之溫度下進行。
- 如請求項1至3中任一項之方法，其中在達到所期望的黏度後，藉由添加起始劑捕捉劑來停止聚合。
- 如請求項13之方法，其中作為該起始劑捕捉劑係使用水與丙酮之混合液、鹼(土)金屬氫氧化物之溶液或鹼(土)金屬烷氧化物之溶液。
- 如請求項1至3中任一項之方法，其中該至少一種液態多官能基環氧化物之聚合係進行至使所產生的環氧漿料具有至少3之多分散性D。
- 一種黏性環氧漿料，其係依據如請求項1至15中任一項之方法製得。
- 如請求項16之黏性環氧漿料，其中在25℃存放下每日的黏度上升係低於5Pa．s。
- 一種黏性環氧漿料，其係包含多官能環氧單體與由此單體所產生的未交聯的多官能聚環氧化物，其特徵在於：該環氧漿料的黏度為所使用的環氧化物在未轉化狀態下之黏度的至少兩倍高。
- 如請求項18之黏性環氧漿料，其具有重量平均莫耳質量Mw至少5,100g/mol。
- 如請求項19之黏性環氧漿料，其具有重量平均莫耳質量Mw最高78,400g/mol。
- 如請求項18至20中任一項之黏性環氧漿料，其中在該環氧漿料中所含的聚環氧化物之分子量分布的範圍至少包括2,000g/mol至300,000g/mol。
- 如請求項18之黏性環氧漿料，其中該環氧單體為3,4-環氧環己甲酸3,4-環氧環己甲酯，且黏度至少達1Pa．s(1,000mPa．s)。
- 一種水氣阻隔性黏著劑，其係包含：一種由以下所構成之黏著劑基質：- 至少一種如請求項16至22中任一項之黏性環氧漿料；- 至少一種彈性體；及- 任選的一種溶劑；其中，該黏著劑基質在反應性樹脂成分活化後具有低於100g/m2．d之水氣通透率。
- 一種膠帶，其係包含如請求項16至22中任一項之黏性環氧漿料或是如請求項23之水氣阻隔性黏著劑。
- 一種如請求項16至22中任一項之黏性環氧漿料之用途，其係用於有機電子裝置中的結構之封裝。
- 一種如請求項23之水氣阻隔性黏著劑之用途，其係用於有機電子裝置中的結構之封裝。
- 一種如請求項24之膠帶之用途，其係用於有機電子裝置中的結構之封裝。
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| DE102015210346.3A DE102015210346A1 (de) | 2015-06-04 | 2015-06-04 | Verfahren zur Herstellung viskoser Epoxidsirupe und danach erhältliche Epoxidsirupe |
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| DE102022117183A1 (de) | 2022-07-11 | 2024-01-11 | Tesa Se | Unvernetztes Polyepoxid und Klebemasse umfassend dieses Polyepoxid |
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| US3729313A (en) | 1971-12-06 | 1973-04-24 | Minnesota Mining & Mfg | Novel photosensitive systems comprising diaryliodonium compounds and their use |
| US3741769A (en) | 1972-10-24 | 1973-06-26 | Minnesota Mining & Mfg | Novel photosensitive polymerizable systems and their use |
| AU497960B2 (en) | 1974-04-11 | 1979-01-25 | Minnesota Mining And Manufacturing Company | Photopolymerizable compositions |
| US4058401A (en) | 1974-05-02 | 1977-11-15 | General Electric Company | Photocurable compositions containing group via aromatic onium salts |
| US4256828A (en) | 1975-09-02 | 1981-03-17 | Minnesota Mining And Manufacturing Company | Photocopolymerizable compositions based on epoxy and hydroxyl-containing organic materials |
| US4138255A (en) | 1977-06-27 | 1979-02-06 | General Electric Company | Photo-curing method for epoxy resin using group VIa onium salt |
| US4231951A (en) | 1978-02-08 | 1980-11-04 | Minnesota Mining And Manufacturing Company | Complex salt photoinitiator |
| US4250053A (en) | 1979-05-21 | 1981-02-10 | Minnesota Mining And Manufacturing Company | Sensitized aromatic iodonium or aromatic sulfonium salt photoinitiator systems |
| US5089536A (en) | 1982-11-22 | 1992-02-18 | Minnesota Mining And Manufacturing Company | Energy polmerizable compositions containing organometallic initiators |
| KR100189642B1 (ko) | 1991-02-18 | 1999-06-01 | 디어터 크리스트 | 전자 부품 및 조립체를 피복시키거나 접착시키는 방법 |
| US5721289A (en) * | 1994-11-04 | 1998-02-24 | Minnesota Mining And Manufacturing Company | Stable, low cure-temperature semi-structural pressure sensitive adhesive |
| JP3973266B2 (ja) * | 1997-07-01 | 2007-09-12 | 横浜ゴム株式会社 | 湿気硬化型１液エポキシ樹脂接着剤組成物 |
| DE19753461A1 (de) | 1997-12-02 | 1999-06-10 | Espe Dental Ag | Lagerstabile kationisch polymerisierende Zubereitungen mit verbessertem Härtungsverhalten |
| US6100007A (en) * | 1998-04-06 | 2000-08-08 | Ciba Specialty Chemicals Corp. | Liquid radiation-curable composition especially for producing cured articles by stereolithography having high heat deflection temperatures |
| PL1954748T3 (pl) * | 2005-11-30 | 2019-02-28 | Ashland Licensing And Intellectual Property Llc | Prepregi i wytworzone z nich utwardzane w miejscu trwałe powierzchnie |
| DE102005062441B4 (de) * | 2005-12-27 | 2012-05-24 | Lohmann Gmbh & Co. Kg | Polymer und ein auf diesem Polymer basierender Strukturklebstoff, sowie Verfahren zur Herstellung dieses Strukturklebstoffs, und dessen Verwendung |
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| DE102012202377A1 (de) | 2011-10-21 | 2013-04-25 | Tesa Se | Klebemasse insbesondere zur Kapselung einer elektronischen Anordnung |
| DE102012206273A1 (de) * | 2012-04-17 | 2013-10-17 | Tesa Se | Vernetzbare Klebmasse mit Hart- und Weichblöcken als Permeantenbarriere |
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| CN106244067A (zh) | 2016-12-21 |
| CA2931499A1 (en) | 2016-12-04 |
| KR102228595B1 (ko) | 2021-03-15 |
| US20210238342A1 (en) | 2021-08-05 |
| JP2017002288A (ja) | 2017-01-05 |
| MX2016006899A (es) | 2016-12-05 |
| US10711087B2 (en) | 2020-07-14 |
| TW201700554A (zh) | 2017-01-01 |
| EP3101047A1 (de) | 2016-12-07 |
| EP3101047B1 (de) | 2020-12-30 |
| KR20160143534A (ko) | 2016-12-14 |
| DE102015210346A1 (de) | 2016-12-08 |
| US20160355634A1 (en) | 2016-12-08 |
| CN106244067B (zh) | 2021-06-01 |
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