TW202118804A - 光可固化(甲基)丙烯酸酯組合物 - Google Patents
光可固化(甲基)丙烯酸酯組合物 Download PDFInfo
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- TW202118804A TW202118804A TW109132233A TW109132233A TW202118804A TW 202118804 A TW202118804 A TW 202118804A TW 109132233 A TW109132233 A TW 109132233A TW 109132233 A TW109132233 A TW 109132233A TW 202118804 A TW202118804 A TW 202118804A
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Abstract
本發明提供一種光可固化(甲基)丙烯酸酯組合物,其用於在膜之表面上且尤其在用於滲透及逆滲透應用(諸如膜過濾器)之膜上形成特徵構件。
Description
本發明係關於包含聚醚丙烯酸胺基甲酸酯及有機填充劑之可固化(甲基)丙烯酸酯組合物及此類組合物之製備方法及使用。更特定而言,本發明係關於光可固化(甲基)丙烯酸酯組合物,其用於在膜之表面上且尤其在用於滲透及逆滲透應用(諸如膜過濾器)之膜上形成特徵構件。
僅舉幾例,可固化組合物已廣泛用於密封、黏合、塗覆及灌注應用。通常參考特定最終使用應用及意欲使用該應用之環境來選擇主結構類型及可固化基團。已使用具有各種程度之不飽和基團的聚合物以及其他官能性交聯基團。
對於逆滲透(RO)膜結合及間隔,常用黏著劑(亦即,可固化組合物)為兩部分室溫下固化聚胺酯或環氧基。必須在膠化時間之前混合及應用兩個部分以形成各部分,其對於一些應用而言係不需要的。已揭示含有(甲基)丙烯酸酯封端之聚丁二烯的光固化丙烯酸酯用於膜摺疊保護,但沒有報導結合至膜。聚丁二烯丙烯酸酯寡聚物通常與許多基板之黏著性低。已知含有聚醚丙烯酸胺基甲酸酯樹脂之光固化丙烯酸酯具有良好的水解穩定性,但在鹼性溶液中結合至RO膜具有挑戰性。
即使初始達成可固化組合物與膜表面之間的充足黏著性,但需要黏著於膜表面之材料(例如間隔物構件)以在固化之後及膜之使用及維護期間維持與膜的良好黏著性。舉例而言,RO膜之使用及維護需要膜表面及黏附至其上之特徵構件/間隔物暴露於水性環境。特定而言,清洗膜通常需要將膜暴露於酸性及鹼性水性溶液。由固化組合物形成之特徵構件可在與水接觸時(特定而言在酸性及鹼性溶液下)面臨降解,使得使用及維護期間之質量、機械強度及與膜之黏著性損失。
需要光可固化(甲基)丙烯酸酯組合物及使用此類組合物以在膜表面上形成水解穩定特徵構件之方法,其使得固化組合物與膜表面具有良好黏著性,以及維護膜之後續使用及維護期間固化組合物之良好黏著性、質量及機械強度。
本發明提供一種光可固化組合物,其包括:a) (甲基)丙烯酸酯官能化聚醚胺基甲酸酯組分;b) (甲基)丙烯酸酯單體;c)有機填充劑;及d)光引發劑,其中當暴露於UV或可見光時,該可固化組合物形成固化反應產物,該固化反應產物表明:1)當在約50℃之溫度下暴露於酸性水性(pH = 1.5)條件下約4週時,質量損失小於2%;及/或2)當在約50℃之溫度下暴露於鹼性水性(pH = 12.5)條件下約4週時,質量損失小於3%。
在本發明之另一態樣中,提供一種複合膜結構,其包括:a)膜,其包含至少一個表面;及b)上文所描述之可固化組合物的固化反應產物,其安置於膜之至少一個表面的至少一部分上。
在本發明之另一態樣中,提供一種產生水解穩定之固化反應產物的方法,其包含以下步驟:a)提供可固化組合物,其包括:i) (甲基)丙烯酸酯官能化聚醚胺基甲酸酯組分;ii) (甲基)丙烯酸酯單體;iii)有機填充劑;及iv)光引發劑;及b)將該可固化組合物暴露於UV或可見光源以形成固化反應產物,其中當該固化反應產物展現出以下質量損失時表明水解穩定性:1)當在約50℃之溫度下暴露於酸性水性(pH = 1.5)條件下約4週時,質量損失小於2%;及/或2)當在約50℃之溫度下暴露於鹼性水性(pH = 12.5)條件下約4週時,質量損失小於3%。
本發明係關於光可固化(甲基)丙烯酸酯組合物,其包括:a) (甲基)丙烯酸酯官能化聚醚胺基甲酸酯組分;b) (甲基)丙烯酸酯單體;c)有機填充劑;及d)光引發劑,其中當暴露於UV或可見光時,可固化組合物形成固化反應產物,該固化反應產物展現出:1)當在約50℃之溫度下暴露於酸性水性(pH = 1.5)條件約4週時,質量損失小於2%,及/或2)當在約50℃之溫度下暴露於鹼性水性(pH = 12.5)條件下約4週時,質量損失小於3%。
如本文中所使用之「水解穩定」意謂固化反應產物在存在水之情況下對化學分解具有抵抗性。此水解穩定性尤其在RO膜應用中係至關重要的,因為在此類複合膜結構之使用及維護期間,固化反應產物(通常連續地)暴露於水性條件。此外,視膜之特定使用而定,固化反應產物可暴露於極高酸性及極高鹼性條件下。舉例而言,RO膜過濾器之清洗或修復包含施加苛性鹼溶液以移除間隔物元件(亦即,由固化反應產物形成之特徵構件)中所捕獲之殘留物及殘渣。因此,固化反應產物之水解穩定性可能對延長此等膜元件之壽命及降低與其頻繁替換相關聯之成本至關重要。
在本發明之一態樣中,當暴露於水性條件(諸如水性溶液)時固化反應產物展現出最少質量損失時表明固化反應產物之水解穩定性。如本文中所使用,「最少質量損失」意謂當在高溫下長時間暴露於水性條件下時質量損失小於5%、小於4%、小於3%、小於2.5%、小於2%、小於1.5%、小於1%或小於0.5%。如本文中所使用,「長時間」意謂約0.5週、約1週、約2週、約3週、約4週、約5週或約6週。如本文中所使用,「高溫」意謂約30℃或更高、約35℃或更高、約40℃或更高、約45℃或更高、約50℃或更高、約55℃或更高、約60℃或更高或約70℃或更高。
在本發明之態樣中,水性條件可包括酸性水性條件、鹼性水性條件及中性水性條件。如本文中所使用,「酸性水性條件」意謂pH為約3或更低、約2.5或更低、約2或更低、約1.5或更低或約1或更低之水性條件。如本文中所使用,「鹼性水性條件」意謂pH為約11或更高、約11.5或更高、約12或更高、約12.5或更高或約13或更高之水性條件。如本文中所使用,「中性水性條件」意謂pH在約6與約8之間或pH為約7之水性條件。
在本發明之一態樣中,當固化反應產物展現出以下質量損失時表明固化反應產物之水解穩定性:1)當在約50℃之溫度下暴露於酸性水性(pH = 1.5)條件下約4週時,質量損失小於2%;及/或2)當在約50℃之溫度下暴露於鹼性水性(pH = 12.5)條件下約4週時,質量損失小於3%。
在本發明之一態樣中,固化反應產物之肖氏D硬度(Shore D hardness)為約20或更高,較佳為約20至約70或約40至約60。
在本發明之一態樣中,可固化組合物之黏度為約10,000至約100,000或約20,000至約80,000厘泊(在25℃,10 s-1
下)。
在本發明之一態樣中,可固化組合物具有最佳化流變性,其有效地平衡以使得具有足夠觸變性以使得易於沈積,且在沈積之後及固化之前仍維持其物理結構。如本文中所使用,「觸變性」意謂當施加應力(例如混合或振盪)時物質變得不太黏稠,及當不含此類應力(例如,在靜態條件下)時物質更黏稠。
在本發明之另一態樣中,可固化組合物之觸變指數為約1.5至約6或約1.5至約5。如本文中所使用,「觸變指數」意謂1 s-1
之速度下的可固化組合物之黏度(以厘泊為單位)與10 s-1
之速度下的可固化組合物之黏度(以厘泊為單位)的比率(1 s-1
下之黏度/10 s-1
下之黏度)。可使用已知方法(例如,椎板流變儀、平行板流變儀或旋轉黏度計(諸如布氏黏度計(Brookfield viscometer))來測定黏度。
在本發明之一態樣中,(甲基)丙烯酸酯官能化聚醚胺基甲酸酯組分為聚醚丙烯酸胺基甲酸酯寡聚物。適合之聚醚丙烯酸胺基甲酸酯寡聚物包括(但不限於)脂族丙烯酸胺基甲酸酯。適合之聚醚丙烯酸胺基甲酸酯寡聚物之實例包括:Ebecryl 264、265、270、1258、4100、4200、4220、4265、8807、8810及8800-20R (全部來自Allnex);BR-14B、BR-302、BR-344、BR-345、BR-372、BR-543、BR-571、BR-582、BR 582E8、BR-930D、BR-3042及BR-3471 (全部來自Dymax);Genomer 4230、4217 (全部來自Rahn);CN 9004、9005、959、989、996及980 (全部來自Sartomer)。亦可使用來自丙烯酸胺基甲酸酯製造商(諸如IGM、Evonik及Kowa)之一些其他聚醚丙烯酸胺基甲酸酯。
在本發明之一態樣中,丙烯酸胺基甲酸酯寡聚物為聚乙二醇二丙烯酸酯(吾等不瞭解聚醚丙烯酸胺基甲酸酯之確切結構)或其組合。
在本發明之另一態樣中, (甲基)丙烯酸酯官能化聚醚胺基甲酸酯組分係以按可固化組合物之總重量計約20重量%至約60重量%或約30重量%至約50重量%之量存在。
適合之(甲基)丙烯酸酯單體包括(甲基)丙烯酸、(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸正丙酯、(甲基)丙烯酸異丙酯、(甲基)丙烯酸正丁酯、(甲基)丙烯酸異丁酯、(甲基)丙烯酸第三丁酯、(甲基)丙烯酸正戊酯、(甲基)丙烯酸正己酯、(甲基)丙烯酸環己酯、(甲基)丙烯酸正庚酯、(甲基)丙烯酸正辛酯、(甲基)丙烯酸2-乙基己酯、(甲基)丙烯酸壬酯、(甲基)丙烯酸癸酯、(甲基)丙烯酸十二烷酯、(甲基)丙烯酸苯酯、(甲基)丙烯酸甲苯酯、(甲基)丙烯酸苯甲酯、(甲基)丙烯酸2-甲氧基乙酯、(甲基)丙烯酸3-甲氧基丁酯、(甲基)丙烯酸2-羥乙酯、(甲基)丙烯酸2-羥丙酯、(甲基)丙烯酸十八烷醯酯、(甲基)丙烯酸縮水甘油酯、(甲基)丙烯酸2-胺基乙酯、γ-(甲基丙烯醯氧基丙基)三甲氧基矽烷、(甲基)丙烯酸-環氧乙烷加合物、(甲基)丙烯酸三氟甲基甲酯、(甲基)丙烯酸2-三氟甲基乙酯、(甲基)丙烯酸2-全氟乙基乙酯、(甲基)丙烯酸2-全氟乙基-2-全氟丁基乙酯、(甲基)丙烯酸2-全氟乙酯、(甲基)丙烯酸全氟甲酯、(甲基)丙烯酸二全氟甲基甲酯、(甲基)丙烯酸2-全氟甲基-2-全氟乙基甲酯、(甲基)丙烯酸2-全氟己基乙酯、(甲基)丙烯酸2-全氟癸基乙酯及(甲基)丙烯酸2-全氟十六烷基乙酯。在本發明之一態樣中,(甲基)丙烯酸酯單體為聚乙二醇二丙烯酸酯,諸如SR 259 (來自Sartomer之聚乙二醇(200)二丙烯酸酯)。適合之多官能(甲基)丙烯酸酯包括聚乙二醇二(甲基)丙烯酸酯、期望之三乙二醇二(甲基)丙烯酸酯、(甲基)丙烯酸羥丙酯、雙酚A二(甲基)丙烯酸酯(諸如乙氧基化雙酚A (甲基)丙烯酸酯(「EBIPA」或「EBIPMA」))及四氫呋喃(甲基)丙烯酸酯及二(甲基)丙烯酸酯、丙烯酸香茅酯及甲基丙烯酸香茅酯、己二醇二(甲基)丙烯酸酯(「HDDA」或「HDDMA」)、三羥甲基丙烷三(甲基)丙烯酸酯、(甲基)丙烯酸四氫二環戊二烯酯、乙氧基化三羥甲基丙烷三丙烯酸酯(「ETTA」)、三乙二醇二丙烯酸酯及三乙二醇二甲基丙烯酸酯(「TRIEGMA」)。在本發明之一態樣中,(甲基)丙烯酸酯單體為單官能或雙官能丙烯酸酯或其組合。
在本發明之一態樣中, (甲基)丙烯酸酯單體係以按可固化組合物之總重量計約10重量%至約60重量%或約20重量%至約40重量%之量存在。
在本發明之另一態樣中,(甲基)丙烯酸酯單體之黏度小於約1,000 cps或小於約500 cps。
在本發明之態樣中,有機填充劑包括基於疏水性聚烯烴之有機增稠劑,熱塑性聚合物,諸如聚乙酸乙烯酯、聚烯烴、耐綸纖維及其組合。適合之有機填充劑包括聚氯乙烯粉末、聚丙烯粉末或其組合。
在本發明之一態樣中,有機填充劑係以按可固化組合物之總重量計約5重量%至約50重量%或約15%至約40%之量存在。
在本發明之態樣中,可固化組合物為光可固化組合物(photocurable/light curable composition),亦即使用諸如可見光或紫外光(UV)之光可固化。在本發明之態樣中,可使用光源(諸如產生可見或UV光之燈泡或LED)固化可固化組合物。
在本發明之一額外態樣中,光引發劑可為UV引發劑、可見光引發劑或UV引發劑及可見光引發劑之組合。在本發明之一個態樣中,光引發劑為附著至少一個發色團之聚合結構,該發色團藉由UV光或可見光範圍內之輻射激發。
可採用各種UV引發劑。UV引發劑通常在200至400 nm範圍內有效,且特定而言接界於不可見光與剛超出此範圍之可見部分的光譜部分(例如>200 nm至約390 nm)中有效。
將回應於UV輻射以引發及誘發(甲基)丙烯基官能化可固化組分之固化的引發劑(其適用於本發明)包括(但不限於)二苯甲酮及經取代之二苯甲酮、苯乙酮及經取代之苯乙酮、安息香及其烷基酯、氧蔥酮(xanthone)及經取代之氧蔥酮、氧化膦、二乙氧基-苯乙酮、安息香甲醚、安息香乙醚、安息香異丙醚、二乙氧基氧蔥酮、氯-硫-氧蔥酮、N-甲基二乙醇-胺-二苯甲酮、2-羥基-2-甲基-1-苯基-丙-1-酮、2-苯甲基-2-(二甲胺基)-1-[4-(4-嗎啉基)苯基]-1-丁酮及其混合物。
此類UV引發劑之實例包括商購自IGM Resins之以下商標名的引發劑:「OMNIRAD」 (先前為「IRGACURE」)及「DAROCUR」,特定而言「OMNIRAD」 184 (1-羥基環己基苯基酮)、907 (2-甲基-1-[4-(甲硫基)苯基]-2-(N-嗎啉基)-丙-1-酮)、369 (2-苯甲基-2-N,N-二甲胺基-1-(4-(N-嗎啉基)苯基)-1-丁酮)、500 (1-羥基環己基苯基酮及二苯甲酮之組合)、651 (2,2-二甲氧基-2-苯基苯乙酮)、1700 (雙(2,6-二甲氧基苯甲醯基-2,4,4-三甲基戊基)磷氧化物及2-羥基-2-甲基-1-苯基-丙-1-酮之組合)及819 [雙(2,4,6-三甲基苯甲醯基)苯基磷氧化物],及「DAROCUR」 1173 (2-羥基-2-甲基-1-苯基-1-丙烷)及4265 (2,4,6-三甲基苯甲醯基二苯基-磷氧化物及2-羥基-2-甲基-1-苯基-丙-1-酮之組合)及2,4,6-三甲基苯甲醯基二苯膦氧化物(作為LUCIRIN TPO商購自BASF Corp.)。當然,在本文中亦可採用此等材料之組合。當然,應理解,本文中歸類為UV光引發劑之一些此等光引發劑具有進入可見範圍內之拖尾吸收,且因此跨越UV光與可見光固化引發劑之間的線,但仍然作為本發明之部分包括於本文中。
適用於本發明之將回應於可見光以引發且誘發固化之引發劑包括(但不限於):樟腦醌過氧化酯引發劑、9-茀羧酸過氧化酯、可見光[藍色]光引發劑、d1-樟腦醌、「IRGACURE」 784DC (基於經取代之二茂鈦的光引發劑)及其組合。
其他適合之光引發劑系統包括以下專利或公開案中之每一者中所揭示之彼等光引發劑系統,該等專利或公開案中之每一者以全文引用之方式併入本文中。
Tamoto等人之美國專利第4,505,793號(其以引用之方式併入本文中)揭示包括經3-酮-取代之香豆素化合物及活性鹵代化合物之組合的光聚合引發劑。揭示大量例示性化合物。此類光聚合引發劑藉由暴露於波長介於約180 nm與600 nm之間的光而固化。
Nagashima等人之美國專利第4,258,123號(其以引用之方式併入本文中)揭示包括用光化光輻照後產生自由基之引發劑組分的感光性樹脂組合物。此等組分包括各種三𠯤化合物,如本文中更充分地描述。
額外適用之組分揭示於以下文件中,其以引用之方式併入本文中。歐洲專利公開案第EP 0 369 645 A1號揭示包括三鹵甲基取代-s-三𠯤 (一種能夠吸收在約300至1000 nm範圍內之輻射的致敏化合物)及電子供體之三部分光引發劑系統。揭示例示性致敏化合物,其包括:酮類;香豆素染料;二苯并哌喃染料、3H-二苯并哌喃-3-酮染料;吖啶染料;噻唑染料;噻𠯤染料;㗁 𠯤染料;吖𠯤染料;胺基酮染料;甲烷及聚甲川染料;卟啉;芳族多環烴類;對位取代之胺基苯乙烯基酮化合物;胺基苯乙烯基甲烷;部花青素(merocyanine);芳酸菁(squarylium)染料;及吡啶染料。亦揭示例示性供體,其包括:胺;醯胺;醚;脲;二茂鐵;亞磺酸及其鹽;亞鐵氰化物之鹽;抗壞血酸及其鹽;二硫基胺基甲酸及其鹽;黃原酸鹽;乙二胺四乙酸鹽;及四苯基酸鹽。此類引發劑對UV光及可見光兩者敏感。
額外適用之組分揭示於以下文件中,其以引用之方式併入本文中。歐洲專利公開案第EP 0 563 925 A1號揭示包括能夠吸收約250至1000 nm範圍內之輻射的致敏化合物及2-芳基-4,6-雙(三氯甲基)-1,3,5-三𠯤之光聚合引發劑。所揭示之例示性致敏化合物包括:花青染料、部花青素染料、香豆素染料、酮香豆素染料、(硫基)二苯并哌喃染料、吖啶染料、噻唑染料、噻𠯤染料、㗁𠯤染料、吖𠯤染料、胺基酮染料、芳酸菁染料、吡啶染料、(硫雜)哌喃鹽染料、卟啉染料、三芳基甲烷染料、(聚)甲烷染料、胺基苯乙烯基化合物及芳族多環烴。此等光聚合引發劑對UV光及可見光敏感。
Neckers等人之美國專利第5,395,862號(其以引用之方式併入本文中)揭示對可見光敏感之螢光酮光引發劑。此類螢光酮引發劑系統亦包括共引發劑,其能夠接受來自經激發之螢光酮物種的電子。揭示例示性共引發劑,其包括:鎓鹽、硝基鹵代甲烷及重氮碸。Neckers等人之美國專利第5,451,343號(以引用之方式併入本文中)揭示螢光酮及派洛甯-Y衍生物作為吸收波長大於350 nm之光的引發劑。Palazzotto等人之美國專利第5,545,676號(其以引用之方式併入本文中)揭示在UV或可見光下固化之三部分光引發劑系統。三部分系統包括芳基碘鎓鹽、致敏化合物及電子供體。例示性碘鎓鹽包括二苯基碘鎓鹽。亦揭示用於三部分系統之例示性致敏劑及電子供體。另外,致敏劑能夠吸收約300至1000 nm範圍內之光。
在本發明之另一態樣中,光引發劑係以按可固化組合物之總重量計約0.2重量%至約5重量%或約1重量%至約3重量%之量存在。
在本發明之一額外態樣中,可固化組合物可進一步包括在酸性及鹼性溶液中保持穩定之無機填充劑。無機填充劑包括煙霧狀二氧化矽。經矽烷處理之煙霧狀二氧化矽、矽酸鹽、矽酸鋁、矽酸鋯、長石、鐵磁體、飛灰、玻璃纖維、黃麻纖維、雲母、石英、二氧化鈦及其組合。
在本發明之一態樣中,無機填充劑係以按可固化組合物之總重量計約0.1重量%至約40重量%或約1重量%至約10重量%之量存在。
視情況選用之添加劑(諸如共引發劑、穩定劑、流變改質劑、消泡劑、抑制劑、去氧劑、染料、顏色、顏料、助黏劑、塑化劑、韌化劑、增強劑、螢光劑、潤濕劑、抗氧化劑及其組合)亦可包括於本發明之組合物中。
本發明亦係關於複合膜結構,其包括:a)膜,其包含至少一個表面;及b)上文所描述之可固化組合物的固化反應產物,其安置於膜之至少一個表面的至少一部分上。
本發明進一步係關於產生水解穩定之固化反應產物的方法,其包括以下步驟:a)提供可固化組合物,其包括:i) (甲基)丙烯酸酯官能化聚醚胺基甲酸酯組分;ii) (甲基)丙烯酸酯單體;iii)有機填充劑;及iv)光引發劑;及b)將可固化組合物暴露於UV或可見光源以形成固化反應產物,其中當該固化反應產物展現出以下質量損失時表明水解穩定性:1)當在約50℃之溫度下暴露於酸性水性(pH = 1.5)條件下約4週時,質量損失小於2%;或2)當在約50℃之溫度下暴露於鹼性水性(pH = 12.5)條件下約4週時,質量損失小於3%。
在本發明之複合膜結構之另一態樣中,固化反應產物黏附性地接合至膜之至少一個表面的至少一部分。
在本發明之複合膜結構之另一態樣中,固化反應產物以預定圖案安置於膜之至少一個表面的至少一部分上。在本發明之複合膜結構之實施例中,預定圖案係選自由以下組成之群:條形、波形、圓形、橢圓形、弧形、正方形、矩形、菱形、五邊形、六邊形、星形、人字形、隨機圖案及其組合。
在本發明之一態樣中,圖案藉由已知方法(諸如在膜表面上印刷或沈積可固化組合物,隨後固化該可固化組合物)形成於膜表面上。藉由本發明之方法形成於膜表面上之圖案通常由許多由固化反應產物形成之特徵構件組成。通常,此等特徵構件具有使其適用於在膜之上覆層之間提供間隔之物理特性。舉例而言,特徵構件可在螺旋逆滲透過濾膜之各層之間提供足夠的間隔,以使採用具有此等特徵構件之膜的逆滲透膜元件之操作、清洗及壽命最佳化。在本發明之一態樣中,特徵構件之圖案可具有足以維持足夠的膜間隔及暴露足夠的膜表面以確保膜之有效操作的大小及形狀。
可固化組合物沈積於其上之表面可包括適用於塗覆可固化組合物之任何膜之表面。在本發明之一態樣中,可固化組合物沈積於其上之表面為膜表面。如本文中所使用,「膜」意謂允許一些物質通過而阻止其他物質通過之選擇性障壁。在本發明之一態樣中,膜為過濾膜,亦即用於自液體載劑(諸如水)過濾出物質之膜。過濾膜包括逆滲透膜、正向滲透膜、微過濾膜、超過濾膜及奈米過濾膜。由固化組合物組成之特徵構件可沈積於膜之活性表面上或膜之非活性表面上,或兩者上。
大體而言,出於例示性及說明性之目的,提供前述描述;本發明並非必需限於此。確切而言,熟習此項技術者將瞭解:額外修改以及對特定環境之調適將屬於如本文中所展示及描述之本發明及本文隨附申請專利範圍之範疇內。實例 材料
在下表1中所描述之實例中採用以下成分:表 1
成分名稱 | 類別 | 供應商 |
聚酯丙烯酸胺基甲酸酯A (專有) | 聚酯丙烯酸胺基甲酸酯 | Henkel |
CN9024 | 聚酯丙烯酸胺基甲酸酯 | Sartomer |
CN991 | 聚酯丙烯酸胺基甲酸酯 | Sartomer |
CN9167US | 聚醚丙烯酸胺基甲酸酯 | Sartomer |
CN996 | 聚醚丙烯酸胺基甲酸酯 | Sartomer |
Ebecryl 8807 | 聚醚丙烯酸胺基甲酸酯 | Allnex |
BR582E8 | 聚醚丙烯酸胺基甲酸酯 | Dymax |
Genomer 4230 | 聚醚丙烯酸胺基甲酸酯 | Rhan |
丙烯酸異冰片酯(IBOA) | 丙烯酸酯單體 | Sartomer |
Genomer 1122 | 丙烯酸酯單體 | Rahn |
丙烯酸異癸酯 | 丙烯酸酯單體 | Sartomer |
聚氯乙烯(PVC)粉末 | 有機填充劑 | Formosa Plastics Corporation |
聚氯乙烯粉末 | 有機填充劑 | BYK |
矽酸鋯粉末 | 有機填充劑 | Continental Mineral Processing |
矽酸鋁粉末 | 有機填充劑 | Continental Mineral Processing |
Aerosil R202 | 經矽烷改質之煙霧狀二氧化矽(無機填充劑) | Evonik |
Omnirad 184 | UV/可見光引發劑(PI) | IGM |
Omnirad TPO | UV/可見光引發劑(PI) | IGM |
Omnirad 1173 | UV/可見光引發劑(PI) | IGM |
聚酯丙烯酸胺基甲酸酯A為來自飽和聚酯二醇與脂族二異氰酸酯反應之可撓性聚酯丙烯酸胺基甲酸酯,其隨後使用羥基丙烯酸酯封端。測試方法
在下文所描述之實例中採用以下測試方法。黏度及觸變指數
使用錐板流變儀(Anton Paar)以1 s-1
及10 s-1
之剪切速率來量測黏度。觸變指數經計算為1 s-1
及10 s-1
下之黏度比率。耐化學性 - 重量百分比變化
將光可固化組合物置放於具有1公釐厚間隔的兩個塑膠薄片之間,且在具有100 mw/cm2
之UV光強度的UV腔室中光固化30秒。將經固化之薄片切割成20公釐長及10公釐寬的矩形樣本。隨後將樣本在50℃或80℃下於pH 1.5鹽酸溶液或pH 12.5氫氧化鈉溶液中浸沒2至4週。
在浸沒之後,用蒸餾水沖洗樣本,且在50℃下乾燥4小時。重量變化百分比經計算為浸沒前後樣本之重量差百分比。肖氏 D 硬度
根據ASTM D2240來量測肖氏D硬度。將測試材料置放於兩個PE薄膜之間且用兩個玻璃板覆蓋以形成1 mm厚之薄片,且隨後使用具有1.5 W/cm2
之強度的LED燈在玻璃板之兩側上固化。隨後將經固化之薄片切割成4片,且接著堆疊以藉由肖氏硬度計來量測。實例 1- 具有各種聚醚及聚酯胺基甲酸酯寡聚物之光可固化組合物
如下表2中所展示,調配具有各種聚醚及聚酯胺基甲酸酯寡聚物之光可固化調配物。表 2
成分 | 類別 | 組合物 /Amt (wt%) | ||||
1-1 | 1-2 | 1-3 | 1-4 | 1-5 | ||
CN 991 | 聚酯胺基甲酸酯寡聚物 | 56.4 | ||||
CN 9024 | 56.4 | |||||
聚酯丙烯酸胺基甲酸酯A | 47 | |||||
Genomer 4230 | 聚醚胺基甲酸酯寡聚物 | 47 | ||||
Ebecryl 8807 | 47 | |||||
IBOA | 丙烯酸酯單體 | 26.32 | 18.8 | 45.12 | 21.62 | 23.5 |
Genomer 1122 | 23.5 | |||||
丙烯酸異癸酯 | 9.4 | 16.92 | 21.62 | |||
Omnirad 184 | 光引發劑 | 0.94 | 0.94 | 0.94 | 0.94 | 0.94 |
Omnirad TPO | 0.94 | 0.94 | 0.94 | 0.94 | 0.94 | |
Aerosil R202 | 無機填充劑 | 6 | 6 | 6 | 6 | 6 |
總計 | 100 | 100 | 100 | 100 | 100 |
固化此等調配物且測試流變性、肖氏硬度及重量百分比變化。結果展示於下表3中。表 3
測試參數 | 組合物 | ||||
1-1 | 1-2 | 1-3 | 1-4 | 1-5 | |
1 s-1 下之黏度(mPa●s) | 127,200 | 50,030 | 45,780 | 160,700 | 88,870 |
10 s-1 下之黏度(mPa●s) | 16,980 | 8,417 | 9,304 | 33,080 | 13,950 |
觸變指數 | 7.49 | 5.94 | 4.92 | 4.86 | 6.37 |
肖氏D硬度 | 68 | 58 | 37 | 55 | 50 |
pH 1.5下浸沒2週之重量百分比變化 | -1.02 | -2.58 | -0.63 | -9.55 | -0.37 |
pH 1.5下浸沒4週之重量百分比變化 | -1.12 | -3.61 | -0.67 | -23.68 | -0.52 |
pH 12.5下浸沒2週之重量百分比變化 | -5.92 | -2.26 | -1.47 | -5.960 | -0.83 |
pH 12.5下浸沒4週之重量百分比變化 | -28.37 | -3.84 | -1.50 | -8.67 | -1.12 |
此等結果表明:應用聚醚丙烯酸胺基甲酸酯之光可固化組合物比應用聚酯丙烯酸胺基甲酸酯具有更佳的水解穩定性(耐化學性),尤其當浸沒於pH 12.5鹼性溶液中時。實例 2- 具有各種胺基甲酸酯寡聚物及填充劑之光可固化組合物
如下文表4中所展示,調配具有各種胺基甲酸酯寡聚物及填充劑之光可固化調配物。針對每一丙烯酸胺基甲酸酯寡聚物,將一種有機填充劑與兩種無機填充劑進行比較。表 4
成分 | 組合物 /Amt (wt%) | ||||||||
2-1 | 2-2 | 2-3 | 2-4 | 2-5 | 2-6 | 2-7 | 2-8 | 2-9 | |
聚酯丙烯酸胺基甲酸酯A (聚酯UA) | 32.5 | 32.5 | 32.5 | ||||||
CN 9024 (聚酯UA) | 39 | 39 | 39 | ||||||
BR582 E8 (聚醚UA) | 32.5 | 32.5 | 32.5 | ||||||
丙烯酸異冰片酯 (單體) | 14.95 | 13 | 14.95 | 14.95 | 13 | 14.95 | 14.95 | 13 | 14.95 |
Genomer 1122 (單體) | 16.25 | 11.7 | 16.25 | 16.25 | 11.7 | 16.25 | 16.25 | 11.7 | 16.25 |
Irgacure 1171 (PI) | 0.65 | 0.65 | 0.65 | 0.65 | 0.65 | 0.65 | 0.65 | 0.65 | 0.65 |
Irgacure TPO (PI) | 0.65 | 0.65 | 0.65 | 0.65 | 0.65 | 0.65 | 0.65 | 0.65 | 0.65 |
Aerosil R202 (無機填充劑) | 8 | 5 | 8 | 8 | 5 | 8 | 8 | 5 | 8 |
PVC 粉末 (有機填充劑) | 30 | 30 | 30 | ||||||
矽酸鋯粉末 (無機填充劑) | 30 | 30 | 30 | ||||||
矽酸鋁粉末 (無機填充劑) | 30 | 30 | 30 | ||||||
總計 | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 100 |
固化此等調配物且測試流變性、肖氏硬度及重量百分比變化。結果展示於下表5中。表 5
測試參數 | 組合物 | ||||||||
2-1 | 2-2 | 2-3 | 2-4 | 2-5 | 2-6 | 2-7 | 2-8 | 2-9 | |
1 s-1 下之黏度(mPa●s) | 3,278 | 1,354 | 3,965 | 4,054 | 696 | 2,027 | 2,931 | 1,014 | 1,756 |
10 s-1 下之黏度(mPa●s) | 134 | 197 | 946 | 132 | 88 | 271 | 192 | 121 | 237 |
觸變指數 | 24.46 | 6.87 | 4.19 | 30.71 | 7.91 | 7.48 | 15.27 | 8.38 | 7.41 |
肖氏D硬度 | 60 | 70 | 45 | 63 | 75 | 50 | 75 | 52 | |
pH 1.5下浸沒4週之重量百分比變化 | -7.03 | -1.45 | -0.18 | -2.37 | -2.46 | -1.26 | -2.87 | -2 | -1.31 |
pH 12.5下浸沒4週之重量百分比變化 | -2.38 | -2.25 | -1.2 | -7.98 | -14.19 | -4.48 | -5.23 | -5.00 | -2.90 |
在浸沒於pH 1.5溶液中之後及浸沒於pH 12.5溶液中之後,含有聚醚丙烯酸胺基甲酸酯(BR582 E8)之調配物(組合物2-3、2-6及2-9)與含有聚酯丙烯酸胺基甲酸酯A之調配物(組合物2-1、2-4及2-7)及含有聚酯丙烯酸胺基甲酸酯(CN 9024)之調配物(組合物2-2、2-5及2-8)相比重量損失均更少。結果與實例1中之結論符合。在pH 12.5溶液中,含有有機填充劑(聚氯乙烯粉末)之調配物(組合物2-1、2-2及2-3)與含有矽酸鋯及矽酸鋁之調配物(分別為組合物2-4、2-5及2-6以及2-7、2-8及2-9)相比重量損失更少。實例 3- 具有各種聚醚胺基甲酸酯寡聚物及有機填充劑之光可固化組合物
如下文表6中所展示,調配具有各種聚醚胺基甲酸酯寡聚物及有機填充劑之光可固化調配物。表 6
成分 | 類別 | 組合物 /Amt (wt%) | |||
3-1 | 3-2 | 3-3 | 3-4 | ||
CN 9167US | 聚醚胺基甲酸酯寡聚物 | 33 | |||
CN 996 | 39.6 | ||||
Genomer 4230 | 32.5 | 32.5 | |||
IBOA | 丙烯酸酯單體 | 18.48 | 15.18 | 31.2 | 31.2 |
丙烯酸異癸酯 | 13.2 | 9.9 | |||
Omnirad 184 | 光引發劑 | 0.66 | 0.66 | 0.65 | 0.65 |
Omnirad TPO | 0.66 | 0.66 | 0.65 | 0.65 | |
Aerosil R202 | 無機填充劑 | 4 | 4 | 5 | 5 |
聚氯乙烯粉末 | 有機填充劑 | 30 | 30 | 30 | |
聚丙烯粉末 | 30 | ||||
總計 | 100 | 100 | 100 | 100 |
固化此等調配物且測試流變性、肖氏硬度及重量百分比變化。結果展示於下表7中。表 7
測試參數 | 組合物 | |||
3-1 | 3-2 | 3-3 | 3-4 | |
1 s-1 下之黏度(mPa●s) | 158,200 | 200,000 | 253,200 | 256,000 |
10 s-1 下之黏度(mPa●s) | 29,370 | 46,790 | 35,720 | 34,460 |
觸變指數 | 5.39 | 4.26 | 7.09 | 7.43 |
肖氏D硬度 | 78 | 65 | 45 | 45 |
pH 1.5下浸沒2週之重量百分比變化 | -0.30 | -0.42 | -0.31 | -0.33 |
pH 1.5下浸沒4週之重量百分比變化 | -0.32 | -0.47 | -0.47 | -0.44 |
pH 12.5下浸沒2週之重量百分比變化 | -0.48 | -0.96 | -1.16 | -0.62 |
pH 12.5下浸沒4週之重量百分比變化 | -0.79 | -1.32 | -1.33 | -0.64 |
此等結果表明:應用聚醚丙烯酸胺基甲酸酯及有機填充劑之光可固化組合物在50℃下浸沒於pH 1.5溶液之後及在50℃下浸沒於pH 12.5溶液中之後均具有良好的水解穩定性(耐化學性)。實例 4- 具有各種聚醚胺基甲酸酯寡聚物與丙烯酸酯單體比率之光可固化組合物
如下表8中所展示,調配具有各種聚醚胺基甲酸酯寡聚物與丙烯酸酯單體比率之光可固化調配物。表 8
成分 | 類別 | 組合物 /Amt (wt%) | ||
4-1 | 4-2 | 4-3 | ||
Genomer 4230 | 聚醚胺基甲酸酯寡聚物 | 55 | 20 | 37.5 |
IBOA | 丙烯酸酯單體 | 20 | 55 | 37.5 |
Omnirad 184 | 光引發劑 | 0.5 | 0.5 | 0.5 |
Omnirad TPO | 0.5 | 0.5 | 0.5 | |
Aerosil R202 | 無機填充劑 | 4 | 4 | 4 |
聚丙烯粉末 | 有機填充劑 | 20 | 20 | 20 |
總計 | 100 | 100 | 100 |
固化此等調配物且測試流變性、肖氏硬度及重量百分比變化。結果展示於下表9中。表 9
測試參數 | 組合物 | ||
4-1 | 4-2 | 4-3 | |
1 s-1 下之黏度(mPa●s) | 107,200 | 22,820 | 52,880 |
10 s-1 下之黏度(mPa●s) | 30,290 | 3,672 | 9,546 |
觸變指數 | 3.54 | 6.21 | 5.54 |
肖氏D硬度 | 24 | 70 | 49 |
pH 1.5下浸沒2週之重量百分比變化 | -0.49 | -0.11 | -0.32 |
pH 1.5下浸沒4週之重量百分比變化 | -0.45 | -0.12 | -0.30 |
pH 12.5下浸沒2週之重量百分比變化 | -0.56 | -0.19 | -0.25 |
pH 12.5下浸沒4週之重量百分比變化 | -0.43 | -0.16 | -0.19 |
此等結果表明:具有各種聚醚胺基甲酸酯寡聚物與丙烯酸酯單體比率之光可固化組合物在50℃下浸沒於pH 1.5溶液中之後及在50℃下浸沒於pH 12.5溶液中之後均全部具有良好的水解穩定性(耐化學性)。實例 5- 具有聚醚胺基甲酸酯寡聚物及各種有機填充劑之光可固化組合物
如下文表10中所展示,調配具有聚醚胺基甲酸酯寡聚物及各種有機填充劑之光可固化調配物。表 10
成分 | 組合物 /Amt (wt%) | |||||||
樹脂 | 5-1 | 5-2 | 5-3 | 5-4 | 5-5 | 5-6 | 5-7 | |
Genomer 4230 (聚醚UA) | 50 | 47 | 26 | 33 | 40 | 26 | 33 | 40 |
丙烯酸異冰片酯 (單體) | 48 | 45.12 | 24.96 | 31.68 | 38.4 | 24.96 | 31.68 | 38.4 |
Omnirad 184 (PI) | 1 | 0.94 | 0.52 | 0.66 | 0.8 | 0.52 | 0.66 | 0.8 |
Omnirad (PI) | 1 | 0.94 | 0.52 | 0.66 | 0.8 | 0.52 | 0.66 | 0.8 |
Aerosil R202 (無機填充劑) | 6 | 3 | 4 | 5 | 3 | 4 | 5 | |
聚丙烯粉末 (有機填充劑) | 45 | 30 | 15 | |||||
PVC粉末 (有機填充劑) | 45 | 30 | 15 | |||||
總計 | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 100 |
固化此等調配物且測試流變性、肖氏硬度及重量百分比變化。結果展示於下表11中。表 11
測試參數 | 組合物 | |||||||
樹脂 | 5-1 | 5-2 | 5-3 | 5-4 | 5-5 | 5-6 | 5-7 | |
1 s-1 下之黏度(mPa●s) | 729 | 45,200 | 1,133,000 | 92,710 | 49,600 | 433,400 | 125,200 | 52,750 |
10 s-1 下之黏度(mPa●s) | 695 | 8,331 | 246,600 | 15,600 | 9,237 | 46,010 | 19,370 | 9,579 |
觸變指數 | 1.05 | 5.43 | 4.56 | 5.94 | 5.37 | 9.42 | 6.46 | 5.51 |
肖氏D硬度 | 25 | 38 | 51 | 48 | 41 | 50 | 45 | 40 |
pH 1.5下浸沒2週之重量百分比變化 | -0.66 | -0.46 | -0.18 | -0.32 | -0.4 | 1.24 | 0.61 | -0.08 |
pH 1.5下浸沒4週之重量百分比變化 | -0.62 | -0.46 | -0.21 | -0.32 | -0.39 | 1.25 | 0.60 | -0.09 |
pH 12.5下浸沒2週之重量百分比變化 | -0.91 | -0.72 | -0.20 | -0.37 | -0.47 | 1.08 | 0.37 | -0.36 |
pH 12.5下浸沒4週之重量百分比變化 | -0.86 | -0.72 | -0.22 | -0.34 | -0.42 | 1.05 | 0.26 | -0.48 |
此等結果表明:不具有填充劑或具有不同範圍之各種有機填充劑之光可固化組合物在50℃下浸沒於pH 1.5溶液中之後及在50℃下浸沒於pH 12.5溶液中之後均全部具有良好的水解穩定性(耐化學性)。然而,調配物中之有機填充劑量會影響黏度。在實例5-6中,重量變化為正,此係因為填充劑會吸收水且在特定測試方法中並未完全移除水。
此等結果表明:具有各種量之有機填充劑之光可固化組合物在50℃下浸沒於pH 1.5溶液中之後及在50℃下浸沒於pH 12.5溶液中之後均全部具有良好的水解穩定性(耐化學性)。
Claims (28)
- 一種光可固化組合物,其包含: a)(甲基)丙烯酸酯官能化聚醚胺基甲酸酯組分; b)(甲基)丙烯酸酯單體; c)有機填充劑;及 d)光引發劑, 其中當暴露於UV或可見光時,該光可固化組合物形成固化反應產物,該固化反應產物表明:1)當在約50℃之溫度下暴露於酸性水性(pH = 1.5)條件下約4週時,質量損失小於2%;及/或2)當在約50℃之溫度下暴露於鹼性水性(pH = 12.5)條件下約4週時,質量損失小於3%。
- 如請求項1之光可固化組合物,其中該固化反應產物之肖氏D硬度(Shore D hardness)為約20或更高。
- 如請求項1之光可固化組合物,其中該光可固化組合物之黏度為約10,000至約100,000 cps。
- 如請求項1之光可固化組合物,其中該光可固化組合物之觸變指數為約1.5至約6。
- 如請求項1之光可固化組合物,其中該(甲基)丙烯酸酯官能化聚醚胺基甲酸酯組分係以按該光可固化組合物之總重量計約20重量%至約60重量%之量存在。
- 如請求項1之光可固化組合物,其中該(甲基)丙烯酸酯官能化聚醚胺基甲酸酯組分為聚醚丙烯酸胺基甲酸酯寡聚物。
- 如請求項1之光可固化組合物,其中該(甲基)丙烯酸酯單體係以按該光可固化組合物之總重量計約10重量%至約60重量%之量存在。
- 如請求項1之光可固化組合物,其中該(甲基)丙烯酸酯單體為聚乙二醇二丙烯酸酯。
- 如請求項1之光可固化組合物,其中該有機填充劑係以按該光可固化組合物之總重量計約0.1重量%至約40重量%之量存在。
- 如請求項1之光可固化組合物,其中該有機填充劑為基於疏水性聚烯烴之有機增稠劑。
- 如請求項1之光可固化組合物,其中該有機填充劑係選自由以下組成之群:聚氯乙烯粉末、聚丙烯粉末及其組合。
- 如請求項1之光可固化組合物,其中該光引發劑係以按該光可固化組合物之總重量計約0.2重量%至約5重量%之量存在。
- 如請求項1之光可固化組合物,其中該光引發劑為附著至少一個發色團之聚合結構,該發色團藉由UV光或可見光範圍內之輻射激發。
- 一種複合膜結構,其包含: a)膜,其包含至少一個表面;及 b)如請求項1之光可固化組合物之該固化反應產物,其安置於該膜之該至少一個表面的至少一部分上。
- 如請求項14之複合膜結構,其中該固化反應產物黏附性地接合至該膜之該至少一個表面的至少一部分。
- 如請求項14之複合膜結構,其中該固化反應產物以預定圖案安置於該膜之該至少一個表面的至少一部分上。
- 如請求項16之複合膜結構,其中該預定圖案係選自由以下組成之群:條形、波形、圓形、橢圓形、弧形、正方形、矩形、菱形、五邊形、六邊形、星形、人字形、隨機圖案及其組合。
- 一種產生水解穩定之固化反應產物之方法,其包含以下步驟: a)提供可固化組合物,其包含: i)(甲基)丙烯酸酯官能化聚醚胺基甲酸酯組分; ii)(甲基)丙烯酸酯單體; iii)有機填充劑;及 iv)光引發劑,及 b)將該可固化組合物暴露於UV或可見光源以形成固化反應產物, 其中當該固化反應產物展現出以下質量損失時表明水解穩定性:1)當在約50℃之溫度下暴露於酸性水性(pH = 1.5)條件下約4週時,質量損失小於2%;或2)當在約50℃之溫度下暴露於鹼性水性(pH = 12.5)條件下約4週時,質量損失小於3%。
- 如請求項18之方法,其中該固化反應產物之肖氏D硬度為約20或更高。
- 如請求項18之方法,其中該(甲基)丙烯酸酯官能化聚醚胺基甲酸酯組分係以按該可固化組合物之總重量計約20重量%至約60重量%之量存在。
- 如請求項18之方法,其中該(甲基)丙烯酸酯官能化聚醚胺基甲酸酯組分為聚醚丙烯酸胺基甲酸酯寡聚物。
- 如請求項18之方法,其中該(甲基)丙烯酸酯單體係以按該可固化組合物之總重量計約10重量%至約60重量%之量存在。
- 如請求項18之方法,其中該(甲基)丙烯酸酯單體為聚乙二醇二丙烯酸酯。
- 如請求項18之方法,其中該有機填充劑係以按該可固化組合物之總重量計約0.1重量%至約40重量%之量存在。
- 如請求項18之方法,其中該有機填充劑為基於疏水性聚烯烴之有機增稠劑。
- 如請求項21之方法,其中該有機填充劑係選自由以下組成之群:聚氯乙烯粉末、聚丙烯粉末及其組合。
- 如請求項18之方法,其中該光引發劑係以按該可固化組合物之總重量計約0.2重量%至約5重量%之量存在。
- 如請求項18之方法,其中該光引發劑為附著至少一個發色團之聚合結構,該發色團藉由UV光或可見光範圍內之輻射激發。
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KR20220065777A (ko) | 2022-05-20 |
US20220204809A1 (en) | 2022-06-30 |
EP4031595A1 (en) | 2022-07-27 |
CN114391026A (zh) | 2022-04-22 |
BR112022004052A2 (pt) | 2022-05-31 |
WO2021055862A1 (en) | 2021-03-25 |
EP4031595A4 (en) | 2023-09-27 |
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