TWI751228B - 硬化性組成物、其硬化物及其硬化方法 - Google Patents
硬化性組成物、其硬化物及其硬化方法 Download PDFInfo
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- TWI751228B TWI751228B TW106140875A TW106140875A TWI751228B TW I751228 B TWI751228 B TW I751228B TW 106140875 A TW106140875 A TW 106140875A TW 106140875 A TW106140875 A TW 106140875A TW I751228 B TWI751228 B TW I751228B
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- meth
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- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
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Abstract
Description
本發明係關於硬化性組成物、其硬化物及其硬化方法,詳言之,係關於光微影性及樹脂溶出性優異之硬化性組成物、其硬化物及其硬化方法。
目前,作為藉由照射光而成不溶化之樹脂,已知有各種具有感光性基之聚合物,關於使用此等聚合物之組成物已有各種提案。例如專利文獻1中提案一種紫外線硬化型墨水,其係噴墨方式之墨水受理性優異並且對於聚碳酸酯基材之接著性等優異之紫外線硬化型墨水,其包含水溶性丙烯酸酯單體與作為水溶性聚合物之聚乙烯吡咯啶酮-乙酸乙烯酯共聚物及胺基甲酸酯丙烯酸酯寡聚物,並且含水率相對於全體量為5重量%以下之值。
又,專利文獻2中,提案一種多彩花樣塗料組成物,其係作為耐水性、耐候性等優異之外裝用塗料,包含將包含合成樹脂乳液、凝膠形成物質及著色顏料等之著色水性塗料分散於含有凝膠化劑之水性介質獲得之著色凝膠粒子,合成樹脂乳液係以(甲基)丙烯酸烷酯為主成分之單體群的乳化聚合物,該單體群中之含羧基之單體比例為3重量%以下。再者,專利文獻3中,提案一種樹脂組成物,其作為環烯烴聚合物用接著劑,含有具有二環戊烯基之(甲基)丙烯酸酯、具有羥基之(甲基)丙烯酸酯、具有二烯系骨架或經氫化之二烯系骨架且不具有(甲基)丙烯醯基之寡聚物、矽烷偶合劑、光聚合起始劑、(甲基)丙烯酸。 [先前技術文獻] [專利文獻]
專利文獻1:日本特開2006-321047號公報 專利文獻2:日本專利第5147096號公報 專利文獻3:日本專利第5684714號公報
[發明欲解決之課題]
上述專利文獻1~3所提案之組成物,含有水溶性多官能(甲基)丙烯酸酯及水溶性聚合物。然而,由該等組合物所製作之膜,光微影性及樹脂溶出性等並不充分,而期望高度兼具該等之組成物。
因此,本發明之目的在於提供光微影性及樹脂溶出性優異之硬化性組成物、其硬化物及其硬化方法。 [用以解決課題之手段]
本發明人等為解決上述課題而積極檢討之結果,發現藉由將硬化性組成物之組成設為如下述,可解決上述課題,因而完成本發明。
亦即,本發明之硬化性組成物之特徵係含有由水溶性多官能(甲基)丙烯酸酯及水溶性多官能(甲基)丙烯醯胺所成之群選擇之至少1種(A),及具有感光性基之水溶性聚合物(B)。
本發明之硬化性組成物中,較好前述水溶性多官能(甲基)丙烯酸酯為以下述通式(I)表示之化合物,(式中,R1
為氫原子、甲基或鹵原子,X1
表示碳原子數1~6之可經羥基取代之伸烷基,A為n價有機基,m為1~30之數,n為2~12之數),前述水溶性多官能(甲基)丙烯醯胺為以下述通式(II)表示之化合物,(式中,R11
表示氫原子或碳原子數1~4之烷基,t為2~12之數,R1
及A與上述通式(I)相同)。且,本發明之硬化性組成物中,較好前述具有感光性基之水溶性聚合物(B)係含有以下述通式(III)或(IV)表示之構成單位的水溶性聚合物:(式中,Y表示2價有機基,Q表示感光性基),或含有以下述通式(V)表示之構成單位的水溶性聚合物:(式中,Anq-
表示q價陰離子,q表示1或2,p為將電荷保持為中性之係數)。再者,本發明之硬化性組成物中,較好前述通式(III)及(IV)中,Q為乙烯基、烯丙基、苯乙烯基、桂皮基、桂皮醯基、亞桂皮基、亞桂皮基乙醯基、查耳酮基、香豆素基、異香豆素基、2,5-二甲氧基二苯乙烯基、馬來醯亞胺基、α-苯基馬來醯亞胺基、2-吡喃酮基、疊氮基、胸腺嘧啶基、醌基、馬來醯亞胺基、尿嘧啶基、嘧啶基、苯乙烯基甲基吡啶鎓基(stilbazolium)、苯乙烯基吡啶鎓基、苯乙烯基喹啉鎓基、環氧基、氧雜環丁基、乙烯醚基、烯丙基醚基、乙醯基丙酮構造或β-二酮構造。且再者,本發明之硬化性組成物中,較好前述具有感光性基之水溶性聚合物(B)係於聚乙烯醇中導入有(甲基)丙烯酸酯或(甲基)丙烯醯胺構造之聚乙烯醇衍生物。又,本發明之硬化性組成物中,較好進而含有自由基起始劑。
又,本發明之硬化物的特徵係使本發明之硬化性組成物硬化而成。
再者,本發明之硬化方法的特徵係藉由活性能量線使本發明之硬化性組成物硬化。 [發明效果]
依據本發明,可提供光微影性及樹脂溶出性優異之硬化性組成物、其硬化物及其硬化方法。本發明之硬化性組成物由於耐熱性、耐水性及耐濕熱性優異,且樹脂溶出性良好,故液晶污染性優異,於作為有利於平板顯示器之各種性能薄膜用接著劑為有用,尤其作為液晶滴下工法用密封劑等之直接與液晶接觸之接著劑為有用。
針對本發明之硬化性組成物、其硬化物及其硬化方法詳細說明。本發明之硬化性組成物含有由水溶性多官能(甲基)丙烯酸酯及水溶性多官能(甲基)丙烯醯胺所成之群選擇之至少1種(A)(以下亦稱為(A)成分),及具有感光性基之水溶性聚合物(B)(以下亦稱為(B)成分)。以下針對各成分依序說明。
<水溶性多官能(甲基)丙烯酸酯、水溶性多官能(甲基)丙烯醯胺> 本發明之硬化性組成物之(A)成分的水溶性多官能(甲基)丙烯酸酯舉例為於水中溶解之多官能(甲基)丙烯酸酯、水分散而乳化之多官能(甲基)丙烯酸酯、或於鹼性水中溶解之多官能(甲基)丙烯酸酯,作為構造舉例為分子內具有自親水性官能基的環氧乙烷基、環氧丙烷基、羥基及羧基所成之群中選擇之一種以上之基者、或環氧乙烷改質、環氧丙烷改質者。此處,所謂(甲基)丙烯酸酯意指丙烯酸酯及甲基丙烯酸酯。
作為上述水溶性多官能(甲基)丙烯酸酯舉例為例如聚乙二醇二丙烯酸酯、三羥甲基丙烷三丙烯酸酯、乙二醇二(甲基)丙烯酸酯、1,4-環己烷二甲醇(甲基)丙烯酸酯、丙二醇二(甲基)丙烯酸酯及丁二醇二(甲基)丙烯酸酯等之烷二醇二(甲基)丙烯酸酯;二乙二醇二(甲基)丙烯酸酯、二丙二醇二(甲基)丙烯酸酯及二丁二醇二(甲基)丙烯酸酯等之二烷二醇二(甲基)丙烯酸酯;三乙二醇二(甲基)丙烯酸酯、三丙二醇二(甲基)丙烯酸酯及三丁二醇二(甲基)丙烯酸酯等之三烷二醇二(甲基)丙烯酸酯;四乙二醇二(甲基)丙烯酸酯、四丙二醇二(甲基)丙烯酸酯及四丁二醇二(甲基)丙烯酸酯等之四烷二醇二(甲基)丙烯酸酯;聚乙二醇二(甲基)丙烯酸酯、聚丙二醇二(甲基)丙烯酸酯及聚丁二醇二(甲基)丙烯酸酯等之聚烷二醇二(甲基)丙烯酸酯;聚醚三(甲基)丙烯酸酯、1,4-丁二醇縮水甘油醚二(甲基)丙烯酸酯、1,6-己二醇縮水甘油醚二(甲基)丙烯酸酯、二乙二醇縮水甘油醚二(甲基)丙烯酸酯、二丙二醇縮水甘油醚二(甲基)丙烯酸酯、羧基-聚己內酯單(甲基)丙烯酸酯、鄰苯二甲酸單羥基乙基(甲基)丙烯酸酯、2-羥基-3-苯氧基丙基(甲基)丙烯酸酯等。
上述水溶性多官能(甲基)丙烯酸酯中,具有下述通式(I)表示之構造者、或具有下述通式(VI)表示之構造者,由於與水之親和性高,故而較佳。
通式(I)中,作為R1
表示之鹵原子舉例為氯、溴、碘、氟。且X1
表示之碳原子數1~6之可經羥基取代之伸烷基舉例為亞甲基、伸乙基、伸丙基、伸丁基、伸異丁基等。
通式(I)中,作為A表示之n價有機基,於n為2時,亦可表示如下述通式(1)。
此處,通式(1)中,X2
表示單鍵、-CR30
R31
-、-NR32
-、二價之碳原子數1~35之脂肪族烴基、碳原子數6~35之芳香族烴基或碳原子數2~35之雜環基、或下述式(2)~(4)表示之任一者之取代基,脂肪族烴基可經-O-、-S-、-CO-、 -COO-、-OCO-或-NH-、或者以氧原子不相鄰地將該等組合之結合基予以中斷,R30
及R31
表示氫原子、碳原子數1~8之烷基、碳原子數6~20之芳基或碳原子數7~20之芳基烷基,Z1
及Z2
分別獨立表示直接鍵、-O-、-S-、>CO、 -CO-O-、-O-CO-、-SO2
-、-SS-、-SO-或>NR33
,R32
及R33
表示氫原子、可具有取代基之碳原子數1~35之脂肪族烴基、可具有取代基之碳原子數6~35之芳香族烴基或可具有取代基之碳原子數2~35之雜環基。又,*意指以*部分與鄰接之基鍵結。
此處,式(2)中,R21
表示氫原子、可具有取代基之苯基、或碳原子數3~10之環烷基,R22
表示碳原子數1~10之烷基、碳原子數1~10之烷氧基、碳原子數2~10之烯基或鹵原子,該等烷基、環烷基及烯基可具有取代基,a為0~5之整數。
此處,式(4)中,R23
及R24
分別獨立表示可具有取代基之碳原子數1~10之烷基、可具有取代基之碳原子數6~20之芳基、可具有取代基之碳原子數6~20之芳基氧基、可具有取代基之碳原子數6~20之芳基硫基、可具有取代基之碳原子數6~20之芳基烯基、可具有取代基之碳原子數7~20之芳基烷基、可具有取代基之碳原子數2~20之雜環基或鹵原子,烷基及芳基烷基中之亞甲基可經不飽和鍵、-O-或-S-中斷,R23
可與鄰接之R23
彼此形成環,b表示0~4之數,c表示0~8之數,g表示0~4之數,h表示0~4之數,g與h之數合計為2~4。且式(2)~(4)中之*,意指以*部分與鄰接之基鍵結。
通式(I)中,作為A表示之n價有機基,於n為3時,亦可表示為如通式(5)。
此處,通式(5)中,Y11
表示單鍵、三價之碳原子數3~35之脂肪族烴基、碳原子數3~35之脂環族烴基、碳原子數6~35之芳香族烴基或碳原子數2~35之雜環基,Z1
、Z2
及Z3
分別獨立表示直接鍵、-O-、-S-、>CO、-CO-O-、 -O-CO-、-SO2
-、-SS-、-SO-、>NR32
、>PR32
或可具有取代基之碳原子數1~35之脂肪族烴基、可具有取代基之碳原子數6~35之芳香族烴基或可具有取代基之碳原子數2~35之雜環基,R32
表示氫原子、可具有取代基之碳原子數1~35之脂肪族烴基、可具有取代基之碳原子數6~35之芳香族烴基或可具有取代基之碳原子數2~35之雜環基,脂肪族烴基可經碳-碳雙鍵、-O-、-CO-、-O-CO-、-CO-O-或-SO2
-中斷。
通式(I)中,作為A表示之n價有機基,於n為4時,亦可表示為如通式(6)。
此處,通式(6)中,Y12
表示單鍵、碳原子或四價之碳原子數1~35之脂肪族烴基、碳原子數6~35之芳香族烴基或碳原子數2~35之雜環基,脂肪族烴基可經-COO-、-O-、 -OCO-、-NHCO-、-NH-或-CONH-中斷,Z1
~Z4
分別獨立表示與上述通式(5)中之Z1
~Z3
表示之基相同範圍之基。
通式(I)中,作為A表示之n價有機基,於n為5時,亦可表示為如通式(7)。
此處,通式(7)中,Y13
表示單鍵、五價之碳原子數2~35之脂肪族烴基、碳原子數6~30之芳香族烴基或碳原子數2~30之雜環基,脂肪族烴基可經-COO-、-O-、-OCO-、-NHCO-、-NH-或-CONH-中斷,Z1
~Z5
分別獨立表示與上述通式(5)中之Z1
~Z3
表示之基相同範圍之基。
通式(I)中,作為A表示之n價有機基,於n為6時,亦可表示為如通式(8)。
此處,通式(8)中,Y14
表示單鍵、六價之碳原子數2~35之脂肪族烴基、碳原子數6~35之芳香族烴基或碳原子數2~35之雜環基,脂肪族烴基可經-COO-、-O-、-OCO-、-NHCO-、-NH-或-CONH-中斷,Z1
~Z6
分別獨立表示與上述通式(5)中之Z1
~Z3
表示之基相同範圍之基。
本發明之硬化性組成物中,通式(I)中,m為5~20,n為3~8時,與水之親和性高故而較佳。
作為水溶性多官能(甲基)丙烯酸酯之較佳者,具體可舉例下述者。
作為水溶性多官能(甲基)丙烯酸酯,亦可使用市售者,舉例為例如A-GLY-9E、A-GLY-20E、A-600、A-1000、A-BPE-30、ATM-35E、A-PG5027E、A-PG5054E、14G、GLY-9E、GLY-20E(新中村化學公司製)、PEG400DA-D、EBECRYL 11(DAICEL ALLNEX製)、9EG-A、14EG-A(共榮社化學)等。
又,本發明之硬化性組成物之(A)成分的水溶性多官能(甲基)丙烯醯胺,舉例為於水中溶解之多官能(甲基)丙烯醯胺、水分散而乳化之多官能(甲基)丙烯醯胺、或於鹼性水中溶解之多官能(甲基)丙烯醯胺。此處,所謂(甲基)丙烯醯胺意指丙烯醯胺及甲基丙烯醯胺。
上述水溶性多官能(甲基)丙烯醯胺中,具有下述通式(II)表示之構造者,與水之親和性較高故而較佳。
作為上述碳數1~4之烷基舉例為甲基、乙基、丙基、異丙基、正丁基、異丁基、第三丁基等。只要未特別記載,則後述之碳數1~4之烷基可較好地使用上述例示之基。
作為水溶性多官能(甲基)丙烯醯胺舉例為例如N,N’-亞甲基丙烯醯胺、N-[三(3-丙烯醯胺丙氧基甲基)甲基](甲基)丙烯醯胺、N,N’-二丙烯醯基-4,7,10-三氧雜-1,13-十三烷二胺、N,N’,N”-三丙烯醯基二伸乙基二胺、N,N’-{[2-丙烯醯胺-2-[(3-醯胺基丙氧基)甲基]丙烷-1,3-二基]雙(氧基)}雙(丙烷-1,3-二基)}二丙烯醯胺、N,N’,N”,N’”-四丙烯醯基三伸乙基四胺等。
本發明之硬化性組成物中,作為水溶性多官能(甲基)丙烯醯胺亦可使用於氮原子上具有羥基烷基等之取代基者。
作為水溶性多官能(甲基)丙烯醯胺之較佳者,具體可舉例為下述者。
作為水溶性多官能(甲基)丙烯醯胺,亦可使用市售者,舉例為例如FFM-2、FFM-3、FFM-4、FFM-5等。
本發明之硬化性組成物中,(A)成分可單獨使用1種,亦可以任意比例組合2種以上。
<具有感光性基之水溶性聚合物> 作為本發明之硬化性組成物之具有感光性基之水溶性聚合物(B)舉例為聚乙烯醇、經矽烷醇基等改質之聚乙烯醇衍生物、於聚乙烯醇中導入(甲基)丙烯酸酯或(甲基)丙烯醯胺構造之聚烯醇衍生物、氧化澱粉、醚化‧酯化‧接枝化改質澱粉、明膠‧酪蛋白‧羧甲基纖維素等之纖維素衍生物、聚乙烯吡咯啶酮、水溶性聚酯樹脂、水溶性聚丙烯酸酯樹脂、水溶性聚碳酸酯樹脂、水溶性聚乙酸乙烯酯樹脂、水溶性苯乙烯丙烯酸酯樹脂、水溶性乙烯基甲苯丙烯酸酯樹脂、水溶性聚胺基甲酸酯樹脂、水溶性聚醯胺樹脂、水溶性脲樹脂、水溶性聚己內酯樹脂、水溶性聚苯乙烯樹脂、水溶性聚氯乙烯樹脂、水溶性聚丙烯酸酯樹脂、水溶性聚丙烯腈樹脂等之水溶性樹脂;於苯乙烯‧丁二烯共聚物、丙烯酸酯共聚物、聚乙酸乙烯酯、乙烯‧乙酸乙烯酯共聚物等之水溶性聚合物中導入乙烯基、烯丙基、苯乙烯基、桂皮基、桂皮醯基、亞桂皮基、亞桂皮基乙醯基、查耳酮基、香豆素基、異香豆素基、2,5-二甲氧基二苯乙烯基、馬來醯亞胺基、α-苯基馬來醯亞胺基、2-吡喃酮基、疊氮基、胸腺嘧啶基、醌基、馬來醯亞胺基、尿嘧啶基、嘧啶基、苯乙烯基甲基吡啶鎓基、苯乙烯基吡啶鎓基、苯乙烯基喹啉鎓基、環氧基、氧雜環丁基、乙烯醚基、烯丙基醚基、乙醯基丙酮構造或β-二酮構造等之感光性基者;對苯乙烯‧丁二烯共聚物、丙烯酸酯共聚物、聚乙酸乙烯酯、乙烯‧乙酸乙烯酯共聚物等之水溶性聚合物接枝具有羥基、羰基、甲醯基等之(甲基)丙烯酸酯或具有羥基之(甲基)丙烯醯胺者。
作為具有感光性基之水溶性聚合物(B)基於容易取得性之觀點,較好為含有以下述通式(III)或(IV)表示之構成單位的水溶性聚合物。
通式(III)、(IV)中,作為Y所表示之2價有機基舉例為上述通式(I)中A所例示者,但基於取得容易性之觀點,尤其較好為碳原子數1~6之伸烷基或伸苯基。
通式(III)、(IV)中,作為Q所表示之感光性基可使用具有可光二聚化之不飽和鍵之官能基,舉例為例如乙烯基、烯丙基、苯乙烯基、桂皮基、桂皮醯基、亞桂皮基、亞桂皮基乙醯基、查耳酮基、香豆素基、異香豆素基、2,5-二甲氧基二苯乙烯基、馬來醯亞胺基、α-苯基馬來醯亞胺基、2-吡喃酮基、疊氮基、胸腺嘧啶基、醌基、馬來醯亞胺基、尿嘧啶基、嘧啶基、苯乙烯基甲基吡啶鎓基、苯乙烯基吡啶鎓基、苯乙烯基喹啉鎓基、環氧基、氧雜環丁基、乙烯醚基、烯丙基醚基、乙醯基丙酮構造或β-二酮構造等。該等係感光性基因光而引起二聚化反應,形成由碳原子所成之4員環並交聯而於溶劑中不溶化者,或者使乙烯基、烯丙基、(甲基)丙烯醯基等之乙烯性不飽和鍵藉由加成聚合而反應藉此於溶劑中不溶化者。
具有通式(III)或(IV)表示之感光性基之水溶性聚合物(B)中,基於反應性之觀點,較好為具有以下述通式(V)表示之構成單位者。
具有感光性基之水溶性聚合物(B)係聚合度為100~5,000,重量平均分子量為10,000~200,000,皂化度(水解率)為85~100時,由於提高耐水性、提高膜之耐久性故而較佳。
具有通式(III)或(IV)表示之感光性基之水溶性聚合物(B)可藉由使聚乙烯醇與具有感光性基之醛在pH5~7之條件下進行縮醛化反應而獲得。
具有通式(III)或(IV)表示之感光性基之水溶性聚合物(B)中,Q為苯乙烯基吡啶鎓基或乙醯乙酸酯基者,由於耐水性及耐熱性高故而較佳,又更好為以下述通式(VII)表示者。
本發明之硬化性組成物中,作為(B)成分,可使用市售品,可舉例為例如BIOSURFINE-AWP(東洋合成工業公司製)或AQUASOL HS (MURAKAMI公司製)。
本發明之硬化性組成物中,(B)成分可單獨使用1種,亦可以任意比率組合2種以上使用。
本發明之硬化性組成物中,(A)成分及(B)成分以質量比計,較好為5:95~90:10。藉由滿足該範圍,可使耐熱性、耐水性、耐濕熱性、光微影性及樹脂溶出性高度均衡。更好為10:90~80:20,特佳為15:75~60:40。
<其他成分> 本發明之硬化性組成物中,根據需要,亦可添加自由基起始劑、增感劑、偶合劑、交聯劑及溶劑。
作為上述自由基起始劑,可使用過去已知之化合物,除了例如日本特開昭57-197289、日本特開平6-228218、日本特開2009-102455、日本特開2012-007071、日本特表2016-510314、WO2014/050551中記載者以外,亦可使用二苯甲酮、噻噸酮、羧基二苯甲酮與其鹽、二羧基二苯甲酮與其鹽、1-氯-4-丙氧基噻噸酮、異丙基噻噸酮、二乙基噻噸酮、乙基蒽醌等之拉氫型光聚合起始劑;苯基聯苯基酮、1-羥基-1-苯甲醯基環己烷(α-羥基苯烷酮)、苯偶因、苄基二甲基縮醛、1-苄基-1-二甲胺基-1-(4’-嗎啉苯甲醯基)丙烷、2-嗎啉-2-(4’-甲基巰基)苯甲醯基丙烷、4-苯甲醯基-4’-甲基二苯基硫化物、苯偶因丁基醚、2-羥基-2-苯甲醯基丙烷、2-羥基-2-(4’-異丙基)苯甲醯基丙烷、4-丁基苯甲醯基三氯甲烷、4-苯氧基苯甲醯基二氯甲烷、苯甲醯基甲酸乙酯、1-羥基-環己基-苯基酮、2-羥基-2-甲基-1-苯基-丙烷-1-酮、1-[4-(2-羥基乙氧基)-苯基]-2-羥基-2-甲基-1-丙烷-1-酮、1,7-雙(9’-吖啶基)庚烷、9-正丁基-3,6-雙(2’-嗎啉異丁醯基)咔唑、2-甲基-4,6-雙(三氯甲基)-s-三嗪、2-苯基-4,6-雙(三氯甲基)-s-三嗪、2-萘基-4,6-雙(三氯甲基)-s-三嗪、2,2-雙(2-氯苯基)-4,5,4’,5’-四苯基-1-2’-雙咪唑、醯基氧化膦、雙醯基氧化膦、三苯基氧化膦等之光分解型光聚合起始劑,基於反應性之觀點,較好為光分解型光聚合起始劑。
光分解型光聚合起始劑中,IRGACURE 2959、IRGACURE819DW (BASF公司製)、ESACURE ONE、ESACURE 1001M、ESACURE KIP 150、ESACURE DP 250(Lamberti公司)等之水溶性起始劑,由於對水之親和性高故而較好。且亦可使用水溶性起始劑以外之IRGACURE907等。
作為上述水溶性起始劑,下述通式(VIII)及(IX)表示之化合物由於與水之親和性高故而亦較佳。
此處,式中,R31
及R32
分別獨立表示氫原子;可經羥基、羧基、鹵原子、氰基或硝基取代或無取代之碳原子數1~12之烷基;可經碳原子數1~4之烷基、羥基、羧基、鹵原子、氰基或硝基取代或無取代之苯基;可經碳原子數1~4之烷基、羥基、羧基、鹵原子、氰基或硝基取代或無取代之芳基烷基;碳原子數2~12之烯基,R31
與R32
亦可連結形成3~6員雜環。
又,R33
及R34
分別獨立表示氫原子;可經羥基、羧基、鹵原子、氰基或硝基取代或無取代之碳原子數1~12之烷基;可經碳原子數1~4之烷基、羥基、羧基、鹵原子、氰基或硝基取代或無取代之苯基;可經碳原子數1~4之烷基、羥基、羧基、鹵原子、氰基或硝基取代或無取代之芳基烷基;碳原子數2~12之烯基,R33
與R34
亦可連結形成3~6員環。
再者,R35
、R36
、R37
及R38
分別獨立表示氫原子、鹵原子、氰基、硝基、羥基;可經鹵原子取代或無取代之碳原子數1~8之烷基。
且再者,R39
分別獨立表示氫原子、羥基、羧基、鹵原子或碳原子數1~4之烷基,n為2以上時可為相同或不同。
又,R40
表示氫原子;可經羥基、羧基、鹵原子、氰基或硝基取代或無取代之碳原子數1~12之烷基;可經碳原子數1~4之烷基、羥基、羧基、鹵原子、氰基或硝基取代或無取代之苯基;可經碳原子數1~4之烷基、羥基、羧基、鹵原子、氰基或硝基取代或無取代之芳基烷基。
再者,上述烷基及芳基烷基中之亞甲基鏈可經-O-或-S-取代,s表示1~12之數。
此處,式(IX)中,R41
及R42
分別獨立表示氫原子;可經羥基、羧基、鹵原子、氰基或硝基取代或無取代之碳原子數1~12之烷基;可經碳原子數1~4之烷基、羥基、羧基、鹵原子、氰基或硝基取代或無取代之苯基;可經碳原子數1~4之烷基、羥基、羧基、鹵原子、氰基或硝基取代或無取代之碳原子數7~30之芳基烷基;碳數2~12之烯基或鹼金屬原子,R41
與R42
亦可連結形成3~6員雜環。
又,R43
及R44
表示氫原子;可經羥基、羧基、鹵原子、氰基或硝基取代或無取代之碳原子數1~12之烷基;可經碳原子數1~4之烷基、羥基、羧基、鹵原子、氰基或硝基取代或無取代之苯基;可經碳原子數1~4之烷基、羥基、碳原子數1~4之烷氧基、胺基、碳原子數1~4之烷硫基、羧基、鹵原子、氰基或硝基取代或無取代之碳原子數7~30之芳基烷基;碳數2~12之烯基,R43
與R44
亦可連結形成3~6員環狀烷。
再者,R45
、R46
、R47
、R48
、R49
、R50
、R52
及R53
分別獨立表示氫原子、鹵原子、氰基、硝基、羧基、羥基;可經鹵原子取代或無取代之碳原子數1~8之烷基;可經碳原子數1~4之烷基、羥基、羧基、鹵原子、氰基或硝基取代或無取代之碳原子數7~30之芳基烷基。
且再者,R51
表示氫原子、鹵原子、氰基、硝基、羧基、羥基;可經鹵原子取代或無取代之碳原子數1~8之烷基;可經碳原子數1~4之烷基、羥基、羧基、鹵原子、氰基或硝基取代或無取代之碳原子數7~30之芳基烷基、-O-
M+
,M表示鹼金屬。
本發明之硬化性組成物中,自由基起始劑之添加量,相對於(A)成分及(B)成分之合計100質量份,較好為0.1~10質量份,更好為0.5~5質量份。
作為上述增感劑,於藉由光照射而硬化時,為可放大光之可適應波長範圍之化合物,舉例為例如二苯甲酮、3-羥基二苯甲酮、4-羥基二苯甲酮、4,4-二羥基二苯甲酮、2-甲基二苯甲酮、3-甲基二苯甲酮、4-甲基二苯甲酮、2,5-二甲基二苯甲酮、3,4-二甲基二苯甲酮、4-甲氧基二苯甲酮、4,4-二甲氧基二苯甲酮、3,3-二甲基-4-甲氧基二苯甲酮、4-苯基二苯甲酮等之二苯甲酮類,苯乙酮、4-甲氧基苯乙酮、2,4-二甲氧基苯乙酮、2,5-二甲氧基苯乙酮、2,6-二甲氧基苯乙酮、4,4-二甲氧基苯乙酮、4-乙氧基苯乙酮、二乙氧基苯乙酮、2,2-二乙氧基苯乙酮、2-乙氧基-2-苯基苯乙酮、4-苯基苯乙酮等之苯乙酮類,蒽醌、羥基蒽醌、1-硝基蒽醌、胺基蒽醌、2-氯蒽醌、2-甲基蒽醌、2-乙基蒽醌、蒽醌磺酸、1,2-苯并蒽醌、1,4-羥基蒽醌(醌茜(quinizarin))等之蒽醌類,蒽、1,2-苯并蒽、9-氰基蒽、9,10-二氰基蒽、2-乙基-9,10-二甲氧基蒽、9,10-雙(苯基乙基)蒽等之蒽類,2,3-二氯-6-二氰基-對-苯醌、2,3-二甲氧基-5-甲基-1,4-苯醌、甲氧基苯醌、2,5-二氯-對-苯醌、2,6-二甲基-1,4-苯醌、9,10-菲醌、樟腦醌、2,3-二氯-1,4-萘醌、氧蒽酮等之醌類,噻噸酮、2-甲基噻噸酮、2,4-二甲基噻噸酮、異丙基噻噸酮、2,4-二乙基噻噸酮、2,4-異丙基噻噸酮等之噻噸酮類,二苯并環庚烯酮(dibenzosuberenone)、二苯并環庚烯、二苯并環庚烯醇、二苯并環庚烷等之環庚烷類,2-甲氧基萘、苯偶因異丙醚、4-苯甲醯基二苯基、鄰-苯甲醯基苯甲酸、鄰-苯甲醯基苯甲酸甲酯、4-苯甲醯基-4-甲基-二苯基硫化物、聯苯醯、苯偶因甲醚等之芳香族化合物,及色素系增感性物質的香豆素系、噻嗪系、嗪系、吖啶系、氧雜蒽系化合物等。
作為上述偶合劑可使用二甲基二甲氧基矽烷、二甲基二乙氧基矽烷、甲基乙基二甲氧基矽烷、甲基乙基二乙氧基矽烷、甲基三甲氧基矽烷、甲基三乙氧基矽烷、乙基三甲氧基矽烷、乙基三甲氧基矽烷等之烷基官能性烷氧基矽烷,乙烯基三氯矽烷、乙烯基三甲氧基矽烷、乙烯基三乙氧基矽烷、烯丙基三甲氧基矽烷等之烯基官能性烷氧基矽烷,3-甲基丙烯醯氧基丙基三乙氧基矽烷、3-甲基丙烯醯氧基丙基三甲氧基矽烷、3-甲基丙烯醯氧基丙基甲基二乙氧基矽烷、3-甲基丙烯醯氧基丙基甲基二甲氧基矽烷、2-甲基丙烯醯氧基丙基三甲氧基矽烷、γ-縮水甘油氧基丙基三甲氧基矽烷、γ-縮水甘油氧基丙基甲基二乙氧基矽烷、β-(3,4-環氧基環己基)乙基三甲氧基矽烷等之環氧官能性烷氧基矽烷,N-β(胺基乙基)-γ-胺基丙基三甲氧基矽烷、γ-胺基丙基三乙氧基矽烷、N-苯基-γ-胺基丙基三甲氧基矽烷等之胺基官能性烷氧基矽烷,γ-巰基丙基三甲氧基矽烷等之巰基官能性烷氧基矽烷、四異丙氧化鈦、四正丁氧化鈦等之烷氧化鈦類,鈦二辛氧基雙(辛二醇)、鈦二異丙氧基雙(乙基乙醯乙酸酯)等之鈦螯合物類,鋯四乙醯乙酸酯、鋯三丁氧基單乙醯乙酸酯等之鋯螯合物類,鋯四丁氧基單硬脂酸酯等之鋯醯化物類,甲基三異氰酸酯矽烷等之異氰酸酯矽烷類等。
作為上述交聯劑,舉例為聚胺類、聚醇類、二氰基二醯胺衍生物、醯肼化合物、聚醯肼化合物(二醯肼、三醯肼)、醛類、羥甲基化合物、活性化乙烯化合物、聚噁唑啉化合物、碳二醯亞胺化合物、環氧化合物、聚異氰酸酯系化合物、酚系化合物、碳酸伸烷酯化合物、多價金屬鹽、矽烷耦合劑、鋯化合物、鈦化合物等。
作為上述溶劑,只要可溶解或分散前述水溶性聚合物等者,則未特別限制,舉例為例如甲基乙基酮、甲基戊基酮、二乙基酮、丙酮、甲基異丙基酮、甲基異丁基酮、環戊酮、環己酮、異佛酮等之酮類;乙醚、二噁烷、四氫呋喃、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷、二丙二醇二甲醚等之醚系溶劑;乙酸甲酯、乙酸乙酯、乙酸正丙酯、乙酸異丙酯、乙酸正丁酯等之酯系溶劑;乙二醇單甲醚、乙二醇單乙醚、丙二醇單甲醚乙酸酯、乙酸溶纖素等之溶纖素溶劑;甲醇、乙醇、異-或正-丙醇、異-或正-丁醇、戊醇、丙酮醇等之醇系溶劑;乙二醇單甲基乙酸酯、乙二醇單乙基乙酸酯、丙二醇甲基乙酸酯等之醚酯系溶劑;苯、甲苯、二甲苯等之BTX系溶劑;己烷、庚烷、辛烷、環己烷等之脂肪族烴系溶劑;萜品油、D-檸檬烯、蒎烯等之萜烯系烴油;礦油精、SWAZOLE #310(COSMO松山石油(股))、SOLVESSO #100(EXXON化學(股))等之鏈烷系溶劑;四氯化碳、氯仿、三氯乙烯、二氯甲烷;1,2-二氯乙烷等之鹵化脂肪族烴系溶劑;氯苯等之鹵化芳香族烴系溶劑;N,N-二甲基甲醯胺、N-甲基吡咯啶酮、二甲基亞碸等之非質子性極性溶劑;卡必醇系溶劑、苯胺、三乙胺、吡啶、乙酸、乙腈、二硫化碳、水等,該等溶劑可使用1種或作為2種以上之混合溶劑使用。
再者,本發明之硬化性組成物中,可根據需要使用界面活性劑。作為上述界面活性劑可使用全氟烷基磷酸酯、全氟烷基碳酸鹽等之氟系界面活性劑、高級脂肪酸鹼鹽、烷基磺酸鹽、烷基硫酸鹽等之陰離子系界面活性劑、高級胺鹵酸鹽、四級銨鹽等之陽離子系界面活性劑、聚乙二醇烷基醚、聚乙二醇脂肪酸酯、山梨糖醇酐脂肪酸酯、脂肪酸單甘油酯等之非離子界面活性劑、兩性界面活性劑、聚矽氧系界面活性劑等之界面活性劑,該等亦可組合使用。
且再者,只要不損及本發明效果,則可根據需要添加熱聚合起始劑、光鹼起始劑、無機填充劑、有機填充劑、顏料、染料等之著色劑、消泡劑、增黏劑、調平劑、有機金屬偶合劑、觸變劑、碳化合物、金屬微粒子、金屬氧化物、難燃劑、可塑劑、光安定劑、熱安定劑、抗老化劑、彈性體粒子、鏈轉移劑、聚合抑制劑、紫外線吸收劑、抗氧化劑、抗靜電劑、脫模劑、流動調整劑、密著促進劑等之各種樹脂添加物等。
本發明之硬化性組成物可藉由旋轉塗佈器、棒塗佈器、輥塗佈器、簾流塗佈器、各種印刷、浸漬等之習知手段,應用於金屬、紙、塑膠等之支撐基體上。且,暫時實施於薄膜等之支撐基體上之後,亦可轉印於其他支撐基體上,其應用方法並未限制。
作為本發明之硬化性組成物之具體用途,可舉例為以眼鏡、攝像用透鏡所代表之光學材料、塗料、塗覆劑、襯底劑、墨水、阻劑、液狀阻劑、接著劑、液晶滴下法用密封劑、印刷版、絕緣清漆、絕緣薄片、層合板、印刷基盤、半導體裝置用‧LED封裝用‧液晶注入口用‧有機EL用‧光元件用‧電絕緣用‧電子零件用‧分離膜用等之密封劑、成形材料、油灰、玻璃纖維含浸劑、填縫劑、半導體用‧太陽電池用等之鈍化膜、層間絕緣膜、保護膜、液晶顯示裝置之背光單元中使用之稜鏡透鏡薄片、投影電視等之螢幕所使用之菲涅耳透鏡薄片、柱狀透鏡薄片等之透鏡薄片之透鏡部,或使用此等薄片之背光單元等、液晶彩色濾光片之保護膜或間隔物、DNA分離晶片、生物感測器、微反應器、奈米生物裝置、硬碟用記錄材料、固體攝性元件、太陽電池面板、發光二極體、有機發光裝置、發光薄膜、螢光薄膜、MEMS元件、致動器、全像術、電漿子裝置、偏光板、偏光薄膜、微透鏡等之光學透鏡、光學元件、光連接器、光波導、光學造型用注模劑等,作為例如於作為塗覆劑可應用之基材,可舉例金屬、木材、橡膠、塑膠、玻璃、陶瓷製品等。
本發明之硬化性組成物作為接著劑使用時,舉例為將於本發明之硬化性組成物中添加適當其他任意成分者予以均一混合,藉由擠出機、輥等混練後,藉由軋光機、輥、T模嘴擠出、吹塑等之製膜法製膜為薄片狀,將成形為薄片狀之接著劑貼附於透明支撐體後,以上述條件自透明支撐體側照射紫外線等之光,隨後貼附於另一被接著體之方法。且,亦可接著於被接著體後照射光。
又,將本發明之硬化性組成物與上述添加劑均一溶解於對於保護薄膜或液晶單元表面基板不造成任何影響之溶劑中,使用網版印刷、凹版印刷、軟版印刷等之印刷法或輥塗佈器塗裝、流動塗佈器塗裝、刮刀塗佈器塗裝等之塗裝方法,均勻塗佈於透明支撐體表面,暫時壓著後,進行光照射而可接著硬化。且於比較狹窄之面接著時,亦有藉接著劑之表面張力滲入所組合之材料間隙之方法。
光照射除光罩以外,可使用灰階遮罩‧半色調遮罩等之多灰階遮罩、稱為網線之高精細遮罩等進行。
作為上述透明支撐體之材料舉例為例如玻璃等之無機材料;二乙醯基纖維素、三乙醯基纖維素(TAC)、丙醯基纖維素、丁醯基纖維素、乙醯基丙醯基纖維素、硝基纖維素等之纖維素酯;聚醯胺;聚碳酸酯;聚對苯二甲酸乙二酯、聚萘二甲酸乙二酯、聚萘二甲酸丁二酯、聚對苯二甲酸1,4-環己烷二亞甲酯、聚乙烯-1,2-二苯氧基乙烷-4,4’-二羧酸酯、聚對苯二甲酸丁二酯等之聚酯;聚苯乙烯;聚乙烯、聚丙烯、聚甲基戊烯等之聚烯烴;聚甲基丙烯酸甲酯等之丙烯酸系樹脂;聚碳酸酯;聚碸;聚醚碸;聚醚酮;聚醚醯亞胺;聚氧乙烯、將冰片烯樹脂等之高分子材料。透明支撐體之透過率較好為80%以上,更好為86%以上。濁度較好為2%以下,更好為1%以下。折射率較好為1.45~1.70。
光照射時所照射之光的波長、強度及照射時間等之照射條件,係根據光聚合起始劑之活性、所使用之光聚合性樹脂之活性等適當調整,但作為波長,通常為了使光充分進入到內部,較好係波長波峰為350~400nm者,更好係波長波峰為360~380nm者。且,作為光強度較好為10~300mW/cm2
,更好為25~100mW/cm2
,照射時間較好為5~500秒,更好為10~300秒。
本發明之硬化性組成物中,為了減少黏度或提高塗佈性,可使用作為反應稀釋劑之液體光聚合性丙烯酸單體、液體光聚合性單乙烯基單體或水溶性單官能(甲基)丙烯醯胺。液體光聚合性丙烯酸單體為市售,或可藉由習知方法製造。作為液體光聚合性單乙烯基單體,舉例為例如乙酸乙烯酯等之乙烯酯;丙烯酸烷酯、甲基丙烯酸烷酯、甲基丙烯酸羥基烷酯、丙烯酸異冰片酯、甲基丙烯酸異冰片酯、丙烯酸二環戊烯酯、甲基丙烯酸二環戊烯酯、(甲基)丙烯酸羥基乙酯等之單丙烯酸酯;丙烯酸或甲基丙烯酸與多元醇之酯;甘油、1,1,1-三羥甲基丙烷、異氰脲酸三羥基乙酯、赤藓醇、季戊四醇等之多元醇等。作為水溶性單官能(甲基)丙烯醯胺,舉例為羥乙基(甲基)丙烯醯胺、(甲基)丙烯醯基嗎啉、二乙基(甲基)丙烯醯胺、二甲胺基丙基(甲基)丙烯醯胺等。
於接著劑層中使用本發明之硬化性組成物之光學薄膜,關於形狀並未特別限制,但通常舉例為於透明支撐體上根據需要設有底塗層、抗反射層、硬塗層、潤滑層、保護層、液晶層等之各層者。作為於光學薄膜設置接著劑層之方法,舉例為(1)塗佈於透明支撐體之方法,(2)將透明支撐體及自任意各層選擇之任意相鄰兩者間設置接著劑層之方法。 [實施例]
以下,針對本發明之硬化性組成物,使用實施例及比較例詳細說明。
[實施例1~14及比較例1~6] 藉由[表1]~[表3]之調配混合各成分,於室溫攪拌1小時後,以1μm過濾器過濾,獲得各實施例及比較例之硬化性組成物。又,實施例及比較例中之份意指質量份。且,[表1]~[表3]中之PV-1~PV-4及PV’-1~PV’-3之調配量,係溶劑除外之成分的比率(質量%)。再者,PV’-1~PV’-3係藉以下順序調整。
製造例:水溶性聚合物水溶液PV’-1~PV’-3之調製 首先,離子交換水90.0g於室溫攪拌,緩慢添加下述比較水溶性聚合物(B’-1、B’-2、B’-3)10.0g。於室溫攪拌1小時後,加熱直至內溫自85℃變為90℃,於該溫度持續攪拌2小時。確認溶解後,冷卻至室溫。調製之水溶液以1μm過濾器過濾。 B’-1:日本合成化學工業製GOHSENOL NL-05 B’-2:日本合成化學工業製G-Polymer OKS-1083 B’-3:日本合成化學工業製GOHSENEX Z-200
針對實施例1~14及比較例1~6所得之硬化性組成物,依據下述順序進行溶液相溶性、塗佈性、光微影性及VHR之評價。結果一併記於[表1]~[表3]。
(溶液相溶性) 將實施例1~14及比較例1~6所得之硬化性組成物之水溶液狀態放入透明樣品瓶中,以目視進行確認。判定基準如下述。 ○:透明均一 △:稍微白濁 ×:白濁、分離或確認到析出物 該評價為○、△者,保存安定性高,可較好地作為硬化性組成物使用,評價為○者特別好。評價為×者,保存安定性低,作為硬化性組成物欠佳。
(塗佈性) 將實施例1~14及比較例1~6所得之硬化性組成物使用旋轉塗佈器塗佈於玻璃基板上之後,以90℃之加熱板進行預烘烤5分鐘。確認此時之膜狀態。又,以膜厚藉觸針法成為5.0~5.5μm之方式調整旋轉塗佈條件。判定基準如下述。 ○:透明均一 △:稍微白濁 ×:白濁、分離或確認到析出物 該評價為○、△者,可較好地作為光學材料所用之硬化性組成物使用,評價為○者特別好。評價為×者,作為光學材料所用之硬化性組成物欠佳。
(光微影性) a)曝光 對於進行預烘烤之基板,透過光罩(線/間隔=100μm/ 100μm),使用高壓水銀燈,對各塗膜以1000mJ/cm2
照射包含365nm之波長的光。
b)顯像、乾燥 將於a)進行曝光之膜於23℃之離子交換水中浸漬1分鐘後,以空氣槍去除附著的水,基板於120℃烘箱內乾燥10分鐘。以雷射顯微鏡確認顯影、乾燥後之圖型,作為光微影性評價。判定基準如下述。 ○:圖型為100±5μm以內者 △:圖型為100±10μm以內者 ×:超過100±10μm或圖型消失者 該評價為○、△者,可較好地作為光微影性為必要之硬化性組成物使用,評價為○者特別好。評價為×者,作為光微影性為必要之硬化性組成物欠佳。
(VHR) 於上述塗佈性試驗中所得之塗膜上,接觸由下述液晶化合物No.1~ No.11所成之液晶組成物,於60℃歷時24小時後,取出液晶組成物而進行樹脂溶出性試驗。針對取出之液晶組成物,比較樹脂溶出性試驗前後之VHR(電壓保持率),求出VHR之降低率,藉由下述基準進行評價。評價係將液晶組成物注入液晶評價用TN單元(單元厚5μm,電極面積8mm×8mm配向膜JALS2096),使用VHR-1A(東陽技術製)測定VHR。(測定條件:脈衝電壓幅度60μs,框週期1.0s,波高±5V,測定溫度25℃)。 ○:VHR之降低率超過99% △:VHR之降低率為97~99% ×:VHR之降低率未達97% 該評價為○、△者,由於樹脂對液晶之溶出低,故可較好地作為樹脂溶出性優異之硬化性組成物使用,評價為○者特別好。評價為×者,由於樹脂對液晶之溶出高故欠佳。
A-1:新中村化學工業公司製NK ESTER A-600(水溶性多官能丙烯酸酯) A-2:新中村化學工業公司製NK ESTER A-GLY-20E(水溶性多官能丙烯酸酯) A-3:新中村化學工業公司製NK ECONOMER A-PG5054E(水溶性多官能丙烯酸酯) A-4:新中村化學工業公司製NK ESTER A-BPE-30(水溶性多官能丙烯酸酯) A-5:富士軟片公司製FFM-2(水溶性多官能丙烯醯胺) A-6:新中村化學工業公司製NK ESTER ATM-35E(水溶性多官能丙烯酸酯) A’-1:新中村化學工業公司製NK ESTER A-400(非水溶性多官能丙烯酸酯) A’-2:新中村化學工業公司製NK ESTER A-BPE-4(非水溶性多官能丙烯酸酯) A’-3:KJ CHEMICALS公司製 羥乙基丙烯醯胺(HEAA)(水溶性單官能丙烯醯胺) PV-1:對GOHSENOL GL-05作用N-羥甲基丙烯醯胺,將固體成分調整為10質量%之水溶液 PV-2:對G-Polymer OKS-1083作用N-羥甲基丙烯醯胺,將固體成分調整為10質量%之水溶液 PV-3:對G-Polymer OKS-1083作用甲醯基苯乙烯基吡啶鎓,將固體成分調整為10質量%之水溶液 PV-4:對GOHSENOL GL-05作用甲醯基苯乙烯基吡啶鎓,將固體成分調整為10質量%之水溶液 C-1:C-2:C-3:C-4:C-5:BASF公司製 IRGACURE907 C-6:BASF公司製 IRGACURE2959 C-7:C-8:C-9:
由[表1]~[表3],可知本發明之硬化性組成物之塗佈性、樹脂溶出性等優異。因此,本發明之硬化性組成物可較好地使用於接著劑。
Claims (8)
- 如請求項2之硬化性組成物,其中前述通式(III)及(IV)中,Q為乙烯基、烯丙基、苯乙烯基、桂皮基、桂皮醯基、亞桂皮基、亞桂皮基乙醯基、查耳酮基、香豆素基、異香豆素基、2,5-二甲氧基二苯乙烯基、馬來醯亞胺基、α-苯基馬來醯亞胺基、2-吡喃酮基、疊氮基、胸腺嘧啶基、醌基、馬來醯亞胺基、尿嘧啶基、嘧啶基、苯乙烯基甲基吡啶鎓基(stilbazolium)、苯乙烯基吡啶鎓基、苯乙烯基喹啉鎓基、環氧基、氧雜環丁基、乙烯醚基、烯丙基醚基、乙醯基丙酮構造或β-二酮構造。
- 如請求項1或2之硬化性組成物,其中前述具有感光性基之水溶性聚合物(B)係於聚乙烯醇中導入有(甲基)丙烯酸 酯或(甲基)丙烯醯胺構造之聚乙烯醇衍生物。
- 如請求項1或2之硬化性組成物,其進而含有自由基起始劑。
- 一種硬化物,其特徵係使如請求項1~6中任一項之硬化性組成物硬化而成。
- 一種硬化方法,其特徵係藉由活性能量線使如請求項1~6中任一項之硬化性組成物硬化。
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- 2017-11-21 CN CN201780067225.0A patent/CN109952329A/zh active Pending
- 2017-11-21 WO PCT/JP2017/041910 patent/WO2018097147A1/ja unknown
- 2017-11-24 TW TW106140875A patent/TWI751228B/zh active
Patent Citations (1)
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TWI238924B (en) * | 1998-03-12 | 2005-09-01 | Goo Chemical Co Ltd | Photosensitive resin composition and photoresist ink for manufacturing printed wiring boards |
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WO2018097147A1 (ja) | 2018-05-31 |
EP3546492A1 (en) | 2019-10-02 |
US20200073239A1 (en) | 2020-03-05 |
JPWO2018097147A1 (ja) | 2019-10-17 |
EP3546492A4 (en) | 2020-07-29 |
JP7057757B2 (ja) | 2022-04-20 |
US11036135B2 (en) | 2021-06-15 |
CN109952329A (zh) | 2019-06-28 |
TW201833157A (zh) | 2018-09-16 |
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