TW202214726A - 包含含有磷酸基之聚合物之塗佈膜形成組成物 - Google Patents
包含含有磷酸基之聚合物之塗佈膜形成組成物 Download PDFInfo
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- TW202214726A TW202214726A TW110122370A TW110122370A TW202214726A TW 202214726 A TW202214726 A TW 202214726A TW 110122370 A TW110122370 A TW 110122370A TW 110122370 A TW110122370 A TW 110122370A TW 202214726 A TW202214726 A TW 202214726A
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Abstract
本發明提供可藉簡易製程於基板上成膜且可維持於包含水的溶劑環境下之膜性能的包含含有磷酸基之聚合物之塗佈膜形成組成物、該組成物之硬化物的塗佈膜。
該塗佈膜形成組成物包含:
含有羥基且該羥基僅源自磷酸基之聚合物(P),
包含以下述式(c-1)表示之構造的聚碳二亞胺(C),
Description
本發明有關包含含有磷酸基之聚合物之塗佈膜形成組成物、該組成物之硬化物的塗佈膜。
含有磷酸基之聚合物已使用於各種用途。作為用途之一,係使用作為具有生物適性之塗佈材料。專利文獻1揭示包含含有磷酸基之聚合物的離子複合材料。專利文獻2揭示使用磷酸聚合物之水性金屬塗料組成物。
[先前技術文獻]
[專利文獻]
[專利文獻1] 國際公開第2014/196650號公報
[專利文獻2] 日本特表2010-505969號公報
[發明欲解決之課題]
本發明之目的在於提供可藉簡單製程於基板上等成膜,於包含水之溶劑環境下可維持生物物附著抑制能及表面親水化等之膜性能之包含含有磷酸基之聚合物的塗佈膜形成組成物、該組成物之硬化物的塗佈膜。
[用以解決課題之手段]
本發明包含以下。
[2] 如[1]之塗佈膜形成組成物,其中前述聚合物(P)包含以式(a)或式(a-1)表示之基,
[式(a)中,U
a1及U
a2分別獨立表示氫原子或碳原子數1~5之烷基,U
a1及U
a2之至少一個為氫原子,式(a-1)中,A表示鹼金屬]。
[3] 如[1]或[2]之塗佈膜形成組成物,其中前述聚合物(P)包含以式(1)表示之單位構造,
[式中,R
11表示氫原子或碳原子數1~5之烷基,X
1表示碳原子數1~5之伸烷基,n1表示1~10之整數,T
1表示前述式(a)或式(a-1)之基]。
[4] 如[1]至[3]中任一項之塗佈膜形成組成物,其中前述聚碳二亞胺(C)包含親水性基。
[5] 如[4]之塗佈膜形成組成物,其中前述親水性基係以下述式(I)表示,
(式中,R
1表示碳原子數1~5之烷基,R
2表示氫原子或甲基,但存在複數個R
2時,該R
2可彼此相同亦可不同,m表示1~30之整數)。
[6] 如[1]至[5]中任一項之塗佈膜形成組成物,其係用以形成具有生物物質之附著抑制能之塗佈膜。
[7] 如[6]之塗佈膜形成組成物,其中前述生物物質為生物高分子。
[8] 一種塗佈膜,其係如[1]至[7]中任一項之塗佈膜形成組成物的塗膜之硬化物。
[9] 一種塗佈膜之製造方法,其包含將如[1]至[7]中任一項之塗佈膜形成組成物塗佈於基體之步驟。
[發明效果]
本發明之包含含有磷酸基之聚合物之塗佈膜形成組成物即使包含水作為溶劑,亦具有保存安定性,進而以該組成物之塗佈膜對於包含水之溶劑等之耐久性優異。本發明之組成物的塗佈膜作為硬化膜於水中亦不溶出而具有生物高分子之附著抑制能。尤其具有對於生物高分子之優異附著抑制能。
<塗佈膜形成組成物>
本發明之含有磷酸基之聚合物之特徵係含有羥基且該羥基僅源自磷酸基之聚合物(P)。
包含使含有磷酸基之單體與含有磷酸基以外之羥基之單體共聚合之共聚物的組成物為已知,但本發明之含有磷酸基之聚合物所具有之羥基僅源自磷酸基。源自磷酸基之羥基,藉由經由下文詳述之聚碳二亞胺(C),引起含有磷酸基之聚合物彼此之交聯反應,而成為對含水溶劑等之耐久性(耐水性)優異之塗佈膜。
前述聚合物(P)較佳包含以式(a)或式(a-1)表示之基,
[式(a)中,U
a1及U
a2分別獨立表示氫原子或碳原子數1~5之烷基,U
a1及U
a2之至少一個為氫原子,式(a-1)中,A表示鹼金屬]。
較佳對於聚合物主鏈於側鏈具有以式(a)或式(a-1)表示之構造。
以前述式(a)或式(a-1)表示之構造較佳包含於聚合物之重複單位構造。
作為前述碳原子數1~5之烷基,舉例為甲基、乙基、正丙基、異丙基、正丁基、異丁基、第二丁基、第三丁基、正戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、1,1-二甲基丙基、1,2-二甲基丙基、2,2-二甲基丙基或1-乙基丙基。U
a1及U
a2較佳為甲基或乙基。
作為前述鹼金屬,舉例為鋰、鈉、鉀、銣、銫及鍅,較佳為鈉或鉀。
聚合物(P)舉例為以下化合物之聚合物。作為化合物之具體例,舉例為甲基丙烯酸酸性磷氧基乙酯、乙烯基膦酸、丙烯酸酸性磷氧基乙酯、甲基丙烯酸3-氯-2-酸性磷氧基丙酯、甲基丙烯酸酸性磷氧基丙酯、甲基丙烯酸酸性磷氧基甲酯、單甲基丙烯酸酸性磷氧基聚氧乙二醇酯、單甲基丙烯酸酸性磷氧基聚氧丙二醇酯等。亦可以使用市售品。作為市售品舉例為HOSMER M(聯合化學(股)製)、PPM-5P(東邦化學(股)製)等。
前述聚合物(P)較佳包含以式(1)表示之單位構造,
[式中,R
11表示氫原子或碳原子數1~5之烷基,X
1表示碳原子數1~5之伸烷基,n1表示1~10之整數,T
1表示前述式(a)或式(a-1)之基]。
作為前述碳原子數1~5之烷基與上述相同。作為R
11較佳為氫原子或甲基。
作為碳原子數1~5之伸烷基,可舉例為亞甲基、伸乙基、伸丙基、三亞甲基、四亞甲基、1-甲基伸丙基、2-甲基伸丙基、二甲基伸乙基、乙基伸乙基、五亞甲基、1-甲基-四亞甲基、2-甲基-四亞甲基、1,1-二甲基-三亞甲基、1,2-二甲基-三亞甲基、2,2-二甲基-三亞甲基、1-乙基-三亞甲基等。該等中,作為X
1較佳選自伸乙基及伸丙基。
作為n1較佳為1~6之整數。
再者本發明之聚合物(P),在不損及本發明之塗佈膜所需性能的範圍內,亦可共聚合任何單體。又任意單體中,羥基係僅源自磷酸基。作為此等單體之例舉例為以式(2-1)或(3-1)表示之化合物:
[式中,R
12及R
13獨立表示氫原子或碳原子數1~5之烷基,X
2及X
3獨立表示碳原子數1~5之伸烷基,T
2表示以下述式(b)表示之基:
(式中,U
b1、U
b2及U
b3獨立表示氫原子或碳原子數1~5之烷基,An
-表示選自由鹵化物離子、無機酸離子、氫氧化物離子及異氰酸酯離子之所成之群之陰離子),T
3表示碳原子數1~18之烷基、碳原子數3~10之環式烴基、碳原子數6~10之芳基、碳原子數7~14之芳烷基或碳原子數7~14之芳氧基烷基]。
作為上述式(2-1)化合物之具體例舉例為(甲基)丙烯酸二甲胺基乙酯、(甲基)丙烯酸二乙胺基乙酯、(甲基)丙烯酸二甲胺基丙酯、(甲基)丙烯酸2-(第三丁胺基)乙酯、甲基丙烯醯基膽鹼氯化物等。
作為上述(3-1)化合物之具體例,可舉例(甲基)丙烯酸丁酯、(甲基)丙烯酸2-乙基己酯、(甲基)丙烯酸月桂酯、(甲基)丙烯酸硬脂酯等之(甲基)丙烯酸的直鏈或支鏈烷酯類;(甲基)丙烯酸環己酯、(甲基)丙烯酸異冰片酯等之(甲基)丙烯酸環狀烷酯;(甲基)丙烯酸苄酯、(甲基)丙烯酸苯乙酯等之(甲基)丙烯酸之芳烷酯類。
作為其他任意單體之例,可舉例乙二醇二(甲基)丙烯酸酯、三乙二醇二(甲基)丙烯酸酯、丙二醇二(甲基)丙烯酸酯、磷酸雙(甲基丙烯醯氧基甲酯)、磷酸雙[2-(甲基丙烯醯氧基)乙酯]、磷酸雙[2-(甲基丙烯醯氧基)丙酯]、三丙烯酸氧次膦基三(氧基-2,1-乙二酯)等之具有2個以上官能基之(甲基)丙烯酸酯化合物。藉由使該等任意單體共聚合,聚合物(P)之一部分亦可部分形成三維交聯。上述聚合物(P)中之任意單體之比例為0莫耳%至50莫耳%。
本發明之聚合物(P)的重量平均分子量若為數千至數百萬左右即可,較佳為5,000~5,000,000。更佳為10,000~2,000,000。重量平均分子量例如可藉由實施例中記載之凝膠濾滲層析法測定。且,聚合物(P)為共聚物時,該共聚物可為隨機共聚物、嵌段共聚物、接枝共聚物之任一者,用以製造該共聚物之共聚合反應其本身未特別限制,可使用自由基聚合或離子聚合或光聚合、利用巨分子、乳液聚合之聚合等之於習知溶液中合成之方法。本發明之塗佈膜形成組成物,根據目的用途,可單獨包含聚合物(P)之任一者,或混合複數聚合物(P),且其比例係可變。
<溶劑>
本發明之塗佈膜形成組成物所包含之溶劑舉例為水、磷酸緩衝生理食鹽水(PBS)及醇。作為醇舉例為碳原子數2~6之醇,例如乙醇、丙醇、異丙醇、1-丁醇、2-丁醇、異丁醇、第三丁醇、1-戊醇、2-戊醇、3-戊醇、1-庚醇、2-庚醇、2,2-二甲基-1-丙醇(新戊醇)、2-甲基-1-丙醇、2-甲基-1-丁醇、2-甲基-2-丁醇(第三戊醇)、3-甲基-1-丁醇、3-甲基-3-戊醇、環戊醇、1-己醇、2-己醇、3-己醇、2,3-二甲基-2-丁醇、3,3-二甲基-1-丁醇、3,3-二甲基-2-丁醇、2-乙基-1-丁醇、2-甲基-1-戊醇、2-甲基-2-戊醇、2-甲基-3-戊醇、3-甲基-1-戊醇、3-甲基-2-戊醇、3-甲基-3-戊醇、4-甲基-1-戊醇、4-甲基-2-戊醇、4-甲基-3-戊醇及環己醇,可單獨使用或使用該等組合之混合溶劑,但基於含磷酸聚合物之溶解性之觀點,較佳選自水、PBS及乙醇。
為了調節本發明之塗佈膜形成組成物中的離子平衡,亦可包含pH調整劑。例如藉由於含有前述共聚物與溶劑之組成物中添加pH調整劑,使該組成物之pH為3.5~8.5,更佳為4.0~8.0而實施。可使用之pH調整劑的種類及其量,係根據前述共聚物之濃度、或其陰離子與陽離子之存在比例等適當選擇。作為pH調整劑之例,可舉例為氨、二乙醇胺、吡啶、N-甲基-D-葡聚糖胺、三(羥基甲基)胺基甲烷等之有機胺;氫氧化鉀、氫氧化鈉等之鹼金屬氫氧化物;氯化鉀、氯化鈉等之鹼金屬鹵化物;硫酸、磷酸、鹽酸、碳酸等之無機酸或其鹼金屬鹽;膽鹼等之四級銨陽離子或該等之混合物(例如磷酸緩衝生理食鹽水等之緩衝液)。該等中,較佳為硫酸、磷酸、鹽酸、碳酸等之無機酸。
本發明之含磷酸基之聚合物(聚合物(P))與聚碳二亞胺(C)之反應認為係遵循以下進行。認為藉由該反應式,進行含磷酸基之聚合物彼此之交聯反應。
本發明之聚碳二亞胺(C)可為源自具有至少1個一級異氰酸酯基之脂肪族二異氰酸酯化合物的聚碳二亞胺化合物,
前述聚碳二亞胺化合物亦可具有於所有末端以具有與異氰酸酯基反應之官能基之有機化合物封端之構造。
例如,前述具有至少1個一級異氰酸酯基之脂肪族二異氰酸酯化合物,可為選自由下述所成之群之至少1種:伸乙基二異氰酸酯、四亞甲基二異氰酸酯、六亞甲基二異氰酸酯、2,2,4-三甲基六亞甲基二異氰酸酯等之鏈式脂肪族異氰酸酯化合物、異佛爾酮二異氰酸酯、1,3-雙(異氰酸酯基甲基)環己烷、降冰片烷二異氰酸酯等之環式脂肪二異氰酸酯化合物及二甲苯二異氰酸酯等之具有芳香環之脂肪二異氰酸酯化合物。
本發明之聚碳二亞胺(C)例如可藉由伴隨前述具有至少1個一級異氰酸酯基之脂肪族二異氰酸酯化合物的脫二氧化碳之縮合反應而得之於分子內具有至少2個以上述式(c-1)表示之碳二亞胺基的異氰酸酯末端聚碳二亞胺,或者亦可為具有其末端以具有與異氰酸酯基反應之官能基的有機化合物封端之構造的聚碳二亞胺。
前述有機化合物具有之前述官能基可為選自羥基、胺基、異氰酸酯基、環氧基及羧基之至少1種。
作為前述有機化合物之例,可舉例為聚乙二醇單甲醚、聚乙二醇單乙醚、聚丙二醇單甲醚、聚丙二醇單乙醚、三乙二醇單甲醚、三乙二醇單乙醚、四乙二醇單甲醚、四乙二醇單乙醚、二乙二醇單甲醚、二乙二醇單乙醚、乙醇、丙醇、丁醇、戊醇、己醇、辛醇、十二烷醇等之具有羥基之有機化合物;甲胺、乙胺、丙胺、丁胺、戊胺、己胺、辛胺、十二烷胺、二乙胺、二丙胺、二丁胺、環己胺、金剛烷胺、烯丙胺、聚氧乙烯月桂胺、聚氧亞甲基硬脂胺、苯胺、二苯胺、3-胺基丙基三甲氧基矽烷、3-胺基丙基三乙氧基矽烷、N-苯基-3-胺基丙基三甲氧基矽烷、2,2-二氟胺、氟苄基胺、三氟乙胺、[[4-(三氟甲基)環己基]甲基]胺或該等之衍生物等之具有胺基之有機化合物;異氰酸丁酯、異氰酸戊酯、異氰酸己酯、異氰酸辛酯、異氰酸十二烷酯、異氰酸環己酯、異氰酸1-金剛烷酯、3-異氰酸酯基丙基三乙氧基矽烷、丙烯酸2-異氰酸酯基乙酯、異氰酸苄酯、異氰酸2-苯基乙酯或該等之衍生物等之具有異氰酸酯基之有機化合物;1,2-環氧庚烷、1,2-環氧己烷、1,2-環氧癸烷、1,2-環氧-5-己烯、乙基縮水甘油醚、2-乙基己基縮水甘油醚、縮水甘油基月桂醚、烯丙基縮水甘油醚、二乙氧基(3-縮水甘油氧基丙基)甲基矽烷、3-[2-(全氟己基)乙氧基]-1,2-環氧丙烷或該等之衍生物等之具有環氧基之有機化合物;乙酸、乙烷酸、丙酸、丁酸、戊酸、己酸、庚酸、辛酸、壬酸、癸酸、環己烷羧酸、金剛烷酸、苯乙酸、苯甲酸、十一碳烯酸或該等之衍生物等之具有羧基之有機化合物等。
前述有機化合物除前述官能基以外,亦可進而具有親水性基。
前述聚碳二亞胺(C)較佳包含親水性基。
前述親水性基較佳以下述式(I)表示:
(式中,R
1表示碳原子數1~5之烷基,R
2表示氫原子或甲基,但存在複數個R
2時,R
2可彼此相同亦可不同,m表示1~30之整數)。作為前述碳原子數1~5之烷基如上述。
作為與異氰酸酯基反應之官能基一起具有親水性基,特別是以上述式(I)表示之親水性基之有機化合物,舉例為例如聚乙二醇單甲醚(MPEG)、四乙二醇單甲醚(MTEG)等,該等可單獨使用,亦可組合2種以上使用。藉由利用此等有機化合物封端異氰酸酯基末端聚碳二亞胺之末端,可獲得導入有以上述式(I)表示之親水性基之聚碳二亞胺(C)。
作為前述聚碳二亞胺(C),可使用國際公開第2018/194102號記載之聚碳二亞胺化合物。此外關於本發明之聚碳二亞胺化合物之細節,可根據國際公開第2018/194102號記載之內容。
前述聚碳二亞胺(C)可使用市售品。作為市售品之商品名,可舉例例如「CARBODILITE V-02」、「CARBODILITE V-02-L2」、「CARBODILITE V-04」、「CARBODILITE E-01」、「CARBODILITE E-02」(均為日清紡化學(股)製,商品名)。
<塗佈膜、塗佈膜之製造方法>
為了形成本發明之塗佈膜,將前述塗佈膜形成組成物塗佈於基板等之基體表面的至少一部分。作為塗佈方法未特別限制,可使用通常之旋塗、浸塗、溶劑澆鑄法等之塗佈法。
前述基板之形狀未特別限制,平板狀、曲面狀、凹凸形狀等均可使用。
本發明之塗佈膜的乾燥步驟,係在大氣下或真空下,較佳於溫度-200℃~200℃之範圍內進行。藉由乾燥步驟,去除塗佈膜形成組成物中之溶劑,同時引起交聯反應,成為硬化物而將塗佈膜固黏於基板上。
塗佈膜於例如室溫(10℃~35℃,例如25℃)亦可乾燥形成,但為了更快形成塗佈膜,例如可在40℃~50℃乾燥。且亦可使用藉由冷凍乾燥法之在極低溫~低溫(-200℃~-30℃左右)之乾燥步驟。冷凍乾燥稱為真空冷凍乾燥,通常以冷媒冷卻要乾燥者,係藉由於真空狀態下使溶劑昇華而去除之方法。冷凍乾燥所使用之一般冷媒舉例為乾冰與甲醇之混合媒介(-78℃)、液態氮(-196℃)等。
乾燥溫度未達-200℃時,一般必須使用非一般之冷媒,缺乏廣泛利用性,並且為了使溶劑昇華而乾燥需要長時間效率差。乾燥溫度超過200℃時,塗佈膜表面之離子結合反應未進行,使表面失去親水性,無法發揮生物物質附著抑制能。更佳之乾燥溫度為10℃~180℃,更佳的乾燥溫度為25℃~150℃。藉由該乾燥步驟,本發明之含磷酸基之聚合物彼此以例如上述反應式所示般,經由聚碳二亞胺化合物引起交聯反應,而成為硬化膜而可形成塗佈膜。
本發明之塗佈膜,除了水以外,對前述<溶劑>具有耐久性。尤其由於對水具有耐久性(耐水性),故本發明之塗佈膜於長時間暴露於含水之溶劑的情況下使用,可發揮效果。
前述乾燥後,為了使塗佈膜上無殘存雜質、未反應單體等,進而為了調節膜中聚合物之離子平衡,期望以選自水及包含電解質之水溶液的一種以上之溶劑進行流水洗滌或超音波清洗等之洗淨。例如,前述水及含有電解質之水溶液可於例如40℃~95℃之範圍加溫。含有電解質之水溶液較佳為PBS、生理食鹽水(僅含氯化鈉者)、杜貝克氏磷酸緩衝生理食鹽水、Tris緩衝生理食鹽水、HEPES緩衝生理食鹽水及巴比妥緩衝生理食鹽水,特佳為PBS。固黏後,即使以水、PBS及醇洗淨,塗佈膜亦不溶出仍牢固地固黏於基材上。形成之塗佈膜即使附著生物物質,隨後亦可以水洗等容易地去除,形成有本發明之塗佈膜的基體表面具有生物物質之附著抑制能。
本發明之塗佈膜的膜厚為10~1000Å,較佳為10~500Å,最佳為20~400Å。
作為前述基體之材質,可舉例玻璃、含金屬化合物或含半金屬化合物或樹脂,但基於廣泛利用性之觀點,較佳使用玻璃或樹脂。含金屬化合物或含半金屬化合物舉例為例如基本成分為金屬氧化物,藉由於高溫之熱處理而燒固之燒結體的陶瓷、矽般之半導體、金屬氧化物或半金屬氧化物(矽氧化物、氧化鋁等)、金屬碳化物或半金屬碳化物、金屬氮化物或半金屬氮化物(矽氮化物等)、金屬硼化物或半金屬硼化物等之無機化合物之成形體等之無機固體材料、鋁、鎳鈦、不鏽鋼(SUS304、SUS316、SUS316L等)等。
作為樹脂,可為天然樹脂或其衍生物或合成樹脂之任一種,作為天然樹脂或其衍生物,較佳使用纖維素、三乙酸纖維素(CTA)、硝基纖維素(NC)、固定有糊精硫酸之纖維素等,作為合成樹脂,較佳使用聚丙烯腈(PAN)、聚醯亞胺(PI)、聚酯系聚合物合金(PEPA)、聚苯乙烯(PS)、聚碸(PSF)、聚對苯二甲酸乙二酯(PET)、聚甲基丙烯酸甲酯 (PMMA)、聚乙烯醇(PVA)、聚胺酯(PU)、乙烯乙烯醇(EVAL)、聚乙烯(PE)、聚酯、聚丙烯(PP)、聚偏氟乙烯(PVDF)、聚醚碸(PES)、聚碳酸酯(PC)、環烯烴聚合物(COP)、聚氯乙烯(PVC)、聚四氟乙烯(PTFE)、超高分子量聚乙烯(UHPE)、聚二甲基矽氧烷(PDMS)、丙烯腈-丁二烯-苯乙烯樹脂(ABS)或鐵氟龍(註冊商標)。
本發明之塗佈膜較佳為具有生物物質之附著抑制能之塗佈膜。
<生物物質>
本發明中,作為生物物質,舉例為蛋白質、糖、病毒、核酸及細胞或該等之組合。
作為蛋白質,舉例為纖維蛋白原、牛血清白蛋白(BSA)、人類白蛋白、各種球蛋白、β-脂蛋白、各種抗體(IgG、IgA、IgM)、過氧化物酶、各種輔體、各種凝集素、纖維素、溶酶、溫·偉伯氏因子(von Willebrand factor)(vWF)、血清γ-球蛋白、肽、蛋清白蛋白、胰島素、 組蛋白、核糖核酸酶、膠原蛋白、細胞色素c,
例如,作為糖舉例為葡萄糖、半乳糖、甘露糖、果糖、肝素、透明質酸,
例如,作為核酸舉例為去氧核糖核酸(DNA)、核糖核酸(RNA),
作為前述細胞,舉例為纖維母細胞、骨髓細胞、B淋巴細胞、T淋巴細胞、中性粒細胞、紅血球、血小板、巨噬細胞、單核細胞、骨細胞、周皮細胞、樹枝狀細胞、角蛋白細胞、脂肪細胞、間質細胞、上皮細胞、表皮細胞、內皮細胞、血管內皮細胞、肝實質細胞、軟骨細胞、卵丘細胞、神經系細胞、膠質細胞、神經元、寡核苷酸細胞、微膠質細胞、星狀膠質細胞、心臟細胞、食道細胞、肌肉細胞(如平滑肌細胞或骨骼肌細胞)、胰腺β細胞、黑色素細胞、造血前驅細胞、單核細胞、胚胎幹細胞(ES細胞)、胚胎腫瘤細胞、胚胎生殖幹細胞、人工多能幹細胞(iPS細胞)、神經幹細胞、造血幹細胞、間質幹細胞、肝幹細胞、胰腺幹細胞、肌肉幹細胞、生殖幹細胞、腸道幹細胞、癌症幹細胞、毛囊幹細胞及各種細胞株(例如HCT116、Huh7、HEK293(人類胎兒腎細胞)、HeLa(人類子宮頸癌細胞株)、HepG2(人類肝癌細胞株)、UT7/TPO(人類白血病細胞株)、CHO(中國倉鼠卵巢細胞株)、MDCK、MDBK、BHK、C-33A、HT-29、AE-1、3D9、Ns0/1、Jurkat、NIH3T3、PC12、S2、Sf9、Sf21、High Five、Vero)等。
該等中,本發明之塗佈膜對於稱為所謂生物聚合物之糖、蛋白質及核酸,具有優異的附著抑制能。
本發明中,所謂具有蛋白質附著抑制能係指藉實施例記載之方法進行之QCM-D測定中,與無塗佈膜相比時之每相對單位面積之質量(%)((實施例之每單位面積之質量(ng/cm
2)/(無塗佈膜之每單位面積之質量(ng/cm
2)))為50%以下,較佳為30%以下,更佳為20%以下;
本發明中,所謂具有細胞之附著抑制能係指與藉用國際公開第2016/093293號記載之方法進行之螢光顯微鏡的無塗佈膜相比時之相對吸光度(WST O.D. 450nm)(%)((實施例之吸光度(WST O.D. 450nm)/(比較例之吸光度(WST O.D. 450nm)))為50%以下,較佳為30%以下,更佳為20%以下。
前述生物物質較佳選自蛋白質或核酸。
[實施例]
以下,基於合成例、實施例、試驗例等,更詳細說明本發明,但本發明不限於此。
下述合成例所示之共聚物的重量平均分子量係藉凝膠濾滲層析法(以下簡稱GFC)或凝膠滲透層析法(以下簡稱GPC)之測定結果。測定條件如下。
<GFC測定條件>
・裝置:Prominence(島津製作所(股)製)
・GFC管柱:TSKgel GMPWXL(7.8mm I.D×30cm)×2~3根
・流速:1.0mL/min
・溶離液:含離子性物質之水溶液或EtOH之混合溶液
・管柱溫度:40℃
・檢測器:RI
・注入濃度:聚合物固形分0.05~0.5質量%
・注入量:100μL
・校正線:三次近似曲線
・標準試料:聚環氧乙烷(Agilent公司製)×10種
<原料組成之測定方法>
含有含磷化合物之原料之各含磷化合物之濃度(質量%)測定係以
31P-NMR進行。使用下述標準物質計算原料中所含之各含磷化合物之絕對濃度(絕對質量%)。
(測定條件)
・模式:逆閘去耦模式(定量模式)
・裝置:varian 400MHz
・溶劑:CD
3OD(氘化甲醇)(30重量%)
・旋轉數:0Hz
・數據點:64000
・翻轉角:90°
・等待時間:70秒
・累積次數:16次,n=4
・標準物質:三甲基磷酸+D
2O(調製75%TMP溶液)
<合成例1>
甲基丙烯酸酸性磷氧基乙酯(製品名:HOSMERM,聯合化學(股)製,乾固法100℃・1小時之不揮發分:91.8%,甲基丙烯酸酸性磷氧基乙酯(44.2質量%),磷酸雙[2-(甲基丙烯醯氧基)乙酯](28.6質量%),其他物質(27.2質量%)之混合物)10g以水冷攪拌,邊滴加5mol/L氫氧化鈉水溶液(5N)(關東化學(股)製)11.49g並維持於35℃以下進行中和。於其中投入純水18.72g,添加2,2’-偶氮雙(N-(2-羧乙基)-2-甲基丙脒)n-水合物(製品名:VA-057,富士軟片和光純藥(股)製)0.05g,於35℃以下充分溶解。進而添加乙醇10.79g充分攪拌而成為均一之上述全部混入之混合液,導入介隔滴加泵之三頸燒瓶中。另一方面,另外將純水68.86g添加於附冷卻管之3頸燒瓶中吹入氮氣,邊攪拌邊升溫至回流溫度。保持該狀態的同時,前述混合液以介隔鐵氟龍管之滴加泵,歷時0.5小時將混合液滴加至純水的沸騰液內。滴加後,在保持上述環境4小時的狀態下加熱攪拌。4小時後冷卻,獲得固形分約9.26質量%之含聚合物(P-1)的清漆119.91g。所得液體之GFC的重量平均分子量約為290,000。
<合成例2>
酸性磷氧基聚丙二醇單甲基丙烯酸酯(環氧丙烷之平均加成莫耳數5)(製品名:PPM-5P,東邦化學工業(股)製,絕對質量%(純度)97.3質量%)6.02g、甲基丙烯醯基膽鹼氯化物約80%水溶液(東京化成工業(股)製)2.54g、甲基丙烯酸丁酯(東京化成工業(股)製)4.15g、乙醇(純正化學(股)製)48.7g及1,1’-偶氮雙(1-環己烷羧酸)二甲酯(製品名:VE-073,富士軟片和光純藥(股)製)32.3mg添加於附冷卻管之4頸燒瓶中,均一攪拌調製混合液。燒瓶內經氮氣置換,邊攪拌邊升溫至回流溫度。以維持上述環境的狀態下加熱攪拌24小時,獲得固形分約19.9質量%之含聚合物(P-2)之清漆。所得液體之GFC的重量平均分子量約為150,000。
<實施例1>
於上述合成例1所得之含聚合物(P-1)的清漆4g中,添加1mol/L鹽酸(1N)(關東化學(股)製)0.38g及純水13.9g充分攪拌。於其中,添加CARBODILITE V-02(日清紡化學(股)製,固形份約40質量%)0.18g並攪拌至均勻。隨後添加乙醇17.81g充分攪拌,調製塗佈膜形成組成物。pH值為7.5。所得塗佈膜形成組成物,以1500rpm以60秒旋轉塗佈於半導體評價用之市售矽晶圓上,以烘箱於70℃乾燥24小時。然後,以PBS及純水進行充分洗淨,獲得形成有塗佈膜之矽晶圓。以光學干涉膜厚度計確認矽晶圓之塗佈膜膜厚為171Å。
<實施例2>
於上述合成例2所得之含聚合物(P-2)的清漆2g中,添加乙醇11.58g、純水21.35g、1N氨水(關東化學(股)製) 5.26g充分攪拌。於其中,添加將CARBODILITE V-02(日清紡化學(股)製,固形份約40質量%)以純水稀釋10倍之溶液1.50g,而調製塗佈膜形成組成物。pH值為9.9。所得塗佈膜形成組成物,以1500rpm/60秒旋轉塗佈於經HMDS處理過之矽晶圓上,於50℃乾燥3小時。然後,以PBS及純水進行充分洗淨後於70℃乾燥1小時,於經HMDS處理過之矽晶圓上獲得塗佈膜。以分光橢圓儀確認經HMDS處理過之矽晶圓上之塗佈膜膜厚為227Å。
<比較例1>
於上述合成例1所得之含聚合物(P)的清漆4g中,添加1mol/L鹽酸(1N)(關東化學(股)製)0.38g及純水14.57g充分攪拌。隨後添加乙醇17.81g充分攪拌,調製塗佈膜形成組成物。pH值為7.5。所得塗佈膜形成組成物,以1500rpm以60秒旋轉塗佈於半導體評價用之市售矽晶圓上,以烘箱於70℃乾燥24小時。然後,以PBS及純水進行充分洗淨,獲得形成有塗佈膜之矽晶圓。以光學干涉膜厚度計確認矽晶圓之塗佈膜膜厚為26Å。
<比較例2>
將市售之矽氧塗佈劑的siliconized L-25(富士系統(股)製)1g添加於純水50g中充分攪拌。所得塗佈膜形成組成物於1500rpm以60秒旋轉塗佈於半導體評價用之市售矽晶圓上,以烘箱於150°C乾燥0.5小時。隨後,以PBS及純水進行充分洗淨,獲得形成有塗佈膜之矽晶圓。
[試驗例1]
<QCM感測器(PS)之製作>
使用UV/臭氧清洗裝置(UV253E,FILGEN(股)製)洗淨經Au蒸鍍之石英振盪器(Q-Sense,QSX304,Biolin Scientific公司製)3分鐘,然後立即於將2-氨基乙烷硫醇(東京化成工業(股)製)0.0772g溶解於乙醇1000mL之溶液中浸漬24小時。以乙醇洗淨感測器表面後,自然乾燥,將聚苯乙烯(Aldrich公司製)1.00g溶解於甲苯99.00g之清漆以3500rpm/30秒以旋轉塗佈機旋轉塗佈於膜感測器側,以120℃/1分鐘乾燥作成QCM感測器(PS)。
<表面處理QCM感測器之製作>
將實施例1、2及比較例1之塗佈膜形成組成物分別以3500rpm/30秒旋轉塗佈於QCM感測器(PS)上,於70℃烘箱中乾燥24小時作為乾燥步驟。然後,以PBS及超純水洗淨過剩而未硬化之塗佈膜形成組成物各2次作為洗淨步驟,進而將各感測器浸漬於PBS中以超音波洗淨5分鐘,獲得以實施例1、2及比較例1之塗佈膜形成組成物進行表面處理過之QCM感測器。比較例2之塗佈膜形成組成物,除了乾燥步驟中為150°C/烘烤30分鐘外,以同樣方式獲得經表面處理過之QCM感測器。
<蛋白質附著試驗:QCM-D測定>
以實施例1以及比較例1及2之塗佈膜形成組成物表面處理過之各QCM感測器,安裝於逸散型石英振盪器微天平QCM-D(E4,Q-Sense,Biolin Scientific公司製),流入PBS直至確立頻率變化於1小時成為1Hz以下之穩定基準線。然後,將穩定之基準線的頻率設為0Hz流動PBS約10分鐘。接著,將γ-球蛋白人類血液來源(Aldrich公司製)以PBS稀釋100μg/mL之溶液流動約30分鐘,隨後再次使PBS流動約20分鐘後讀取9次泛音(overtone)之吸附感應頻率之偏移(Δf)。作為對照,對於無塗佈膜之PS感測器亦進行同樣試驗。為了分析,使用Q-Tools(Q-Sense,Biolin Scientific公司製),吸附感應頻率之偏移(Δf)係將以Sauerbrey式說明之吸附感應頻率之偏移(Δf)換算為每單位面積之質量(ng/cm
2),作為蛋白質之附著量示於表1,將每單位面積質量之時間依存性的圖表示於圖1。經本發明之塗佈膜形成組成物表面處理過之QCM感測器(實施例1)與經比較例之塗佈膜形成組成物表面處理過之QCM感測器(比較例1及2)及無塗佈膜之PS感測器相比,顯示顯著低的蛋白質附著量。
[試驗例2]
<DNA附著試驗:QCM-D測定>
以與試驗例1同樣製作之經實施例1及比較例1及2之塗佈膜形成組成物表面處理過之各QCM感測器,安裝於逸散型石英振盪器微天平QCM-D(E4,Q-Sense,Biolin Scientific公司製),流入PBS直至確立頻率變化於1小時成為1Hz以下之穩定基準線。然後,將穩定之基準線的頻率設為0Hz流動PBS約10分鐘。接著,將去氧核糖核酸鈉鹽人類胎盤來源(Aldrich公司製)以PBS稀釋100μg/mL之溶液流動約30分鐘,隨後再次使PBS流動約20分鐘後讀取9次泛音之吸附感應頻率之偏移(Δf)。作為對照,對於無塗佈膜之PS感測器亦進行同樣試驗。為了分析,使用Q-Tools (Q-Sense,Biolin Scientific公司製),吸附感應頻率之偏移(Δf)係將以Sauerbrey式說明之吸附感應頻率之偏移(Δf)換算為每單位面積之質量(ng/cm
2),作為DNA之附著量示於表2,將每單位面積質量之時間依存性的圖表示於圖2。經本發明之塗佈膜形成組成物表面處理過之QCM感測器(實施例1)與經比較例之塗佈膜形成組成物表面處理過之QCM感測器(比較例1及2)及無塗佈膜之PS感測器相比,顯示顯著低的DNA附著量。
[試驗例3]
<DNA吸附抑制試驗;螢光強度測定>
將實施例1之塗佈膜形成組成物及比較例1之塗佈膜形成組成物以150μL/管放入聚丙烯(PP)製1.5mL試管(Thermo Fisher Scientific製),於50℃完全乾燥。然後,以純水進行充分洗淨,獲得形成有塗佈膜之PP製1.5mL試管。接著使用添加有0.1M NaCl之10mM Tris-EDTA緩衝液(pH7.4) (富士軟片和光純藥(股))將Human Genomic DNA (TAKARA BIO INC.)調製為2ng/μL,並將100μL放入形成有塗佈膜之PP製1.5mL試管中。作為對照係於未形成塗佈膜之PP製1.5mL試管(非塗佈管)中同樣放入Human Genomic DNA。各試管於40℃保存7天。保存後,回收Human Genomic DNA溶液,於聚苯乙烯製黑色微孔板(康寧公司製)上於DNA溶液5μL中添加QuantiFluor(註冊商標)ONE dsDNA System(Promega公司製)95μL。使用Enspire多模式板閱讀器(Perkin Elmer公司製)測定Ex. 504nm、Em. 531nm算出DNA濃度。
作為本試驗之結果,於各管保存後未附著於試管而殘存之Human Genomic DNA示於表3。
[試驗例4]
<蛋白質附著試驗;QCM-D測定>
以與試驗例1同樣的方法製作之經實施例2之塗佈膜形成組成物表面處理過之QCM感測器,安裝於逸散型石英振盪器微天平QCM-D(E4,Q-Sense,Biolin Scientific公司製),流入PBS 100小時。然後,將穩定之基準線的頻率設為0Hz流動PBS約10分鐘。接著,將,γ-球蛋白人類血液來源(Aldrich公司製)以PBS稀釋100μg/mL之溶液流動約30分鐘,隨後再次使PBS流動約20分鐘後讀取9次泛音之吸附感應頻率之偏移(Δf)。作為對照,對於無塗佈膜之PS感測器亦進行同樣試驗。為了分析,使用Q-Tools(Q-Sense,Biolin Scientific公司製),吸附感應頻率之偏移(Δf)係將以Sauerbrey式說明之吸附感應頻率之偏移(Δf)換算為每單位面積之質量(ng/cm
2),作為蛋白質之附著量示於表4,將每單位面積質量之時間依存性的圖表示於圖3。經本發明之塗佈膜形成組成物表面處理過之QCM感測器(實施例2)與無塗佈膜之PS感測器相比,顯示顯著低的蛋白質附著量。
根據本發明,藉由本發明之包含含有磷酸基之聚合物的塗佈膜形成組成物,可提供對於包含水之溶劑等具有優異耐久性之塗佈膜、具有生物物質之附著抑制能之塗佈膜、對蛋白質及核酸具有優異之附著抑制能之塗佈膜。
[圖1]係以每單位面積之質量的時間依存性的圖表顯示試驗例1中評價之對於以實施例1及比較例1及2之塗佈膜形成組成物進行過表面處理之QCM感測器之蛋白質附著試驗(QCM-D測定)的結果。
[圖2]係以每單位面積之質量的時間依存性的圖表顯示試驗例2中評價之對於以實施例1及比較例1及2之塗佈膜形成組成物進行過表面處理之QCM感測器之DNA附著試驗(QCM-D測定)的結果。
[圖3]係以每單位面積之質量的時間依存性的圖表顯示試驗例4中評價之對於以實施例2之塗佈膜形成組成物進行過表面處理之QCM感測器之蛋白質附著試驗(QCM-D測定)的結果。
Claims (9)
- 如請求項1至3中任一項之塗佈膜形成組成物,其中前述聚碳二亞胺(C)包含親水性基。
- 如請求項1至5中任一項之塗佈膜形成組成物,其係用以形成具有生物物質之附著抑制能之塗佈膜。
- 如請求項6之塗佈膜形成組成物,其中前述生物物質為生物高分子。
- 一種塗佈膜,其係如請求項1至7中任一項之塗佈膜形成組成物的塗膜之硬化物。
- 一種塗佈膜之製造方法,其包含將如請求項1至7中任一項之塗佈膜形成組成物塗佈於基體之步驟。
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