TWI783002B - 樹脂組成物、積層體及其製造方法、電極、二次電池及電雙層電容器 - Google Patents
樹脂組成物、積層體及其製造方法、電極、二次電池及電雙層電容器 Download PDFInfo
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- TWI783002B TWI783002B TW107123033A TW107123033A TWI783002B TW I783002 B TWI783002 B TW I783002B TW 107123033 A TW107123033 A TW 107123033A TW 107123033 A TW107123033 A TW 107123033A TW I783002 B TWI783002 B TW I783002B
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Abstract
本發明藉由如下的樹脂組成物來提供一種高強度、高彈性係數,且水溶液的長期穩定性高、填料的分散性、作為黏合劑的黏結性良好的樹脂組成物,所述樹脂組成物包含:(a)樹脂,含有聚醯亞胺、聚醯胺醯亞胺及聚苯并噁唑中的至少一種,於側鏈具有酚性羥基、羧基及磺酸基中的至少一種酸性官能基,該酸性官能基的濃度為3.4 mol/kg以上;以及(b)鹼性化合物。
Description
本發明是有關於一種樹脂組成物、積層體及其製造方法、電極、二次電池及電雙層電容器。
鋰離子電池作為能夠充電的高電容電池,能夠實現電子機器的高功能化或長時間動作。進而,鋰離子電池搭載於汽車等,有力被視為混合動力車、電動汽車的電池。
目前廣泛使用的鋰離子電池具有將包含鈷酸鋰等活性物質與聚偏二氟乙烯(Polyvinylidene difluoride,PVDF)等黏合劑的漿料塗佈於鋁箔上而形成者作為正極。且具有將包含碳系活性物質與PVDF或苯乙烯.丁二烯.橡膠(Styrene butadiene rubber,SBR)等黏合劑的漿料塗佈於銅箔上而形成者作為負極。
為了使鋰離子電池的電容進一步變大,正研究使用矽、鍺或錫作為負極活性物質(例如,參照專利文獻1)。使用矽、鍺、錫等的負極活性物質可大量地接收鋰離子,因此充分地進行充電時與充分地進行放電時的體積的變化大。另一方面,所述PVDF、SBR等黏合劑中無法追隨活性物質的體積變化。
因此,正研究將更高強度、高彈性係數的聚醯亞胺系樹脂作為負極的黏合劑(例如,參照專利文獻2)。但是,聚醯亞胺樹脂
一般僅溶解於N-甲基吡咯啶酮或N,N'-二甲基乙醯胺等有機溶劑中,存在環境負荷高的問題。因此,不斷推進將樹脂混合於水系溶媒中並用作水系黏合劑的研究。
關於聚醯亞胺系樹脂的水溶液,已知有使水溶性有機胺或咪唑系化合物加成於聚醯亞胺前驅物而成者的水溶液(例如,參照專利文獻3~專利文獻4)、或將於側鏈導入羥基、羧基或磺酸基的聚醯亞胺與鹼金屬的氫氧化物等混合的水溶液(例如,參照專利文獻5、非專利文獻1)。
[現有技術文獻]
[非專利文獻]
[非專利文獻1]「大分子研討會(Macromol Symposia)」, 1996, 106, p. 345-351
[專利文獻]
[專利文獻1]日本專利特開2009-199761號公報
[專利文獻2]日本專利特開2009-245773號公報
[專利文獻3]日本專利特開平8-3445號公報
[專利文獻4]日本專利特開2002-226582號公報
[專利文獻5]日本專利特開2011-137063號公報
然而,專利文獻3~專利文獻4中記載的聚醯亞胺前驅物的水溶液中存在聚合物主鏈進行水解而導致水溶液劣化的問題。另外,專利
文獻5及非專利文獻1中記載的聚醯亞胺樹脂的水溶液中樹脂於水中的溶解性低,因此存在製成水溶液時的長期穩定性不充分的問題。進而,經離子化的側鏈與填料的相互作用小,於將該水溶液設為漿料時存在無法獲得充分的填料分散性或作為黏合劑的黏結性的問題。
本發明鑒於所述課題,其目的在於提供一種高強度、高彈性係數且水溶液的長期穩定性高、填料的分散性、作為黏合劑的黏結性良好的樹脂組成物。
本發明為一種樹脂組成物,其包含:(a)樹脂,含有聚醯亞胺、聚醯胺醯亞胺及聚苯并噁唑中的至少一種,於側鏈具有酚性羥基、羧基及磺酸基中的至少一種酸性官能基,該酸性官能基的濃度為3.4莫耳(mol)/kg以上;以及(b)鹼性化合物。
根據本發明,可獲得一種高強度、高彈性係數且水溶液的長期穩定性高、填料的分散性、作為黏合劑的黏結性良好的樹脂組成物。
以下,對本發明的樹脂組成物、積層體及其製造方法、電極、二次電池及電雙層電容器的較佳的實施形態加以詳細說明。再者,本發明並不受該些實施形態限定。
<樹脂組成物>
本發明的實施形態的樹脂組成物為如下的樹脂組成物,其包含:(a)樹脂,含有聚醯亞胺、聚醯胺醯亞胺及聚苯并噁唑中的至少一種,於側鏈具有酚性羥基、羧基及磺酸基中的至少一種酸性官能基,該酸性官能基的濃度為3.4mol/kg以上;以及(b)鹼性化合物。
((a)樹脂)
(a)包含聚醯亞胺、聚醯胺醯亞胺及聚苯并噁唑中的至少一種的樹脂於側鏈具有酚性羥基、羧基及磺酸基中的至少一種酸性官能基。藉由(a)的樹脂於側鏈具有酸性官能基,於水中的溶解性優異。
就進一步提高於水中的溶解性的方面而言,(a)的樹脂較佳為於所有重複單元中包含50莫耳%以上的於側鏈含有酚性羥基、羧基及磺酸基中的至少一種的重複單元結構。(a)的樹脂的所述重複單元結構的含量更佳為70莫耳%以上,進而佳為90莫耳%以上。
聚醯亞胺例如為使二胺與四羧酸或其衍生物進行反應而獲得的聚合物。聚醯亞胺中的二胺殘基較佳為具有酚性羥基、羧基及磺酸基中的至少一種。
聚醯胺醯亞胺例如為使二胺與三羧酸或其衍生物進行反應而獲得的聚合物。聚醯胺醯亞胺中的二胺殘基較佳為具有酚性羥基、羧基及磺酸基中的至少一種。
聚苯并噁唑例如為使具有羥基的二胺與二羧酸或其衍生物
進行反應而獲得的聚合物。聚苯并噁唑中的二羧酸殘基較佳為具有酚性羥基、羧基及磺酸基中的至少一種。
作為二胺的較佳的具體例,可列舉:雙(3-胺基-4-羥基苯基)六氟丙烷、雙(3-胺基-4-羥基苯基)碸、雙(3-胺基-4-羥基苯基)丙烷、雙(3-胺基-4-羥基苯基)亞甲基、雙(3-胺基-4-羥基苯基)醚、雙(3-胺基-4-羥基)聯苯、雙(3-胺基-4-羥基苯基)茀、雙(4-胺基-3-羥基苯基)六氟丙烷、雙(4-胺基-3-羥基苯基)碸、雙(4-胺基-3-羥基苯基)丙烷、雙(4-胺基-3-羥基苯基)亞甲基、雙(4-胺基-3-羥基苯基)醚、雙(4-胺基-3-羥基)聯苯、雙(4-胺基-3-羥基苯基)茀之類的具有羥基的二胺、或3-羧基-4,4'-二胺基二苯基醚、3,5-二胺基苯甲酸、3,4-二胺基苯甲酸、3,3'-二羧基-4,4'-二胺基二苯基甲烷、4,4'-二羧基-3,3'-二胺基二苯基甲烷、雙(3-胺基-4-羧基苯基)碸、2,2-雙(3-胺基-4-羧基苯基)丙烷、2,2-雙(3-胺基-5-羧基苯基)丙烷、2,2-雙(4-胺基-3-羧基苯基)丙烷、2,2-雙(3-胺基-4-羧基苯基)六氟丙烷、2,2-雙(3-胺基-5-羧基苯基)六氟丙烷、2,2-雙(4-胺基-3-羧基苯基)六氟丙烷、雙(3-胺基-4-羧基苯基)醚等含羧基的二胺、3-磺酸-4,4'-二胺基二苯基醚等含磺酸基的二胺及該些的芳香環經氫化的化合物等。
另外,於不損及水溶液的長期穩定性的範圍內,亦可將具有酚性羥基、羧基及磺酸基中的至少一種的二胺以外的二胺(其他二胺)用作共聚成分。作為其他二胺的較佳的具體例,可列舉:3,4'-二胺基二苯基醚、4,4'-二胺基二苯基醚、3,3'-二胺基二苯基醚、3,4'-二胺基二苯基甲烷、4,4'-二胺基二苯基甲烷、3,3'-二胺基二苯基甲烷、
3,4'-二胺基二苯基碸、4,4'-二胺基二苯基碸、3,3'-二胺基二苯基碸、3,4'-二胺基二苯基硫醚、4,4'-二胺基二苯基硫醚、3,3'-二胺基二苯基硫醚、1,4-雙(4-胺基苯氧基)苯、間苯二胺、對苯二胺、1,5-萘二胺、2,6-萘二胺、雙[4-(4-胺基苯氧基)苯基]碸、雙[4-(3-胺基苯氧基)苯基]碸、4,4'-雙(4-胺基苯氧基)聯苯、雙[4-(4-胺基苯氧基)苯基]醚、2,2'-二甲基-4,4'-二胺基聯苯、2,2'-二乙基-4,4'-二胺基聯苯、3,3'-二甲基-4,4'-二胺基聯苯、3,3'-二乙基-4,4'-二胺基聯苯、2,2',3,3'-四甲基-4,4'-二胺基聯苯、3,3',5,5'-四甲基-4,4'-二胺基聯苯、2,2'-二(三氟甲基)-4,4'-二胺基聯苯及該些的芳香環經氫化的化合物等。
於(a)的樹脂為聚苯并噁唑的情況下,可較佳地使用以上示出的具有羥基的二胺。
作為四羧酸或其衍生物的較佳的具體例,可列舉:均苯四甲酸、3,3',4,4'-聯苯四羧酸、2,3,3',4'-聯苯四羧酸、2,2',3,3'-聯苯四羧酸、3,3',4,4'-二苯甲酮四羧酸、2,2',3,3'-二苯甲酮四羧酸、2,2-雙(3,4-二羧基苯基)六氟丙烷、2,2-雙(2,3-二羧基苯基)六氟丙烷、1,1-雙(3,4-二羧基苯基)乙烷、1,1-雙(2,3-二羧基苯基)乙烷、雙(3,4-二羧基苯基)甲烷、雙(2,3-二羧基苯基)甲烷、雙(3,4-二羧基苯基)碸、雙(3,4-二羧基苯基)醚、1,2,5,6-萘四羧酸、2,3,6,7-萘四羧酸、2,3,5,6-吡啶四羧酸、3,4,9,10-苝四羧酸等芳香族四羧酸、或1,2,3,4-環丁烷四羧酸、1,2,3,4-環戊烷四羧酸、環己烷四羧酸、雙環[2.2.1.]庚烷四羧酸、雙環[3.3.1.]四羧酸、雙環[3.1.1.]庚-2-烯-四羧酸、雙環[2.2.2.]辛烷四羧酸、金剛烷四羧酸、雙環[2,2,2]辛-7-烯-2,3,5,6-四羧酸、內
消旋-丁烷-1,2,3,4-四羧酸、1,2,3,4-丁烷四羧酸等脂肪族四羧酸、以及該些四羧酸的二酐、或1,3,3a,4,5,9b-六氫-5(四氫-2,5-二氧代-3-呋喃基)萘并[1,2-c]呋喃-1,3-二酮、3-(羧基甲基)-1,2,4-環戊烷三羧酸1,4:2,3-二酐等。
作為三羧酸或其衍生物的較佳的具體例,可列舉:偏苯三甲酸、均苯三甲酸、二苯基醚三羧酸、聯苯三羧酸、以及該些三羧酸的酐等。
作為二羧酸或其衍生物的較佳的具體例,可列舉:3,5-二羧基苯酚、2,4-二羧基苯酚、2,5-二羧基苯酚之類的具有羥基的二羧酸、3,5-二羧基苯磺酸、2,4-二羧基苯磺酸、2,5-二羧基苯磺酸之類的具有磺酸基的二羧酸等。
另外,於不損及水溶液的長期穩定性的範圍內,亦可將具有酚性羥基、羧基及磺酸基中的至少一種的二羧酸以外的二羧酸(其他二羧酸)用作共聚成分。作為其他二羧酸的較佳的具體例,可列舉:對苯二甲酸、間苯二甲酸、二苯基醚二羧酸、二苯基碸二羧酸、二苯基甲烷二羧酸、聯苯二羧酸、2,2'-雙(羧基苯基)丙烷、2,2'-雙(羧基苯基)六氟丙烷等。
另外,(a)的樹脂亦可與聚醯亞胺、聚醯胺醯亞胺及聚苯并噁唑以外的樹脂(其他樹脂)混合來使用。作為其他樹脂的較佳的具體例,可列舉:丙烯酸樹脂、甲基丙烯酸樹脂、乙烯基樹脂、苯酚樹脂及纖維素樹脂等。作為特佳的例子,可列舉:聚乙烯基醇、聚乙烯基吡咯啶酮及羧基甲基纖維素。
此時,就樹脂組成物的強度及彈性係數的觀點而言,(a)的樹脂較佳為包含樹脂整體的80莫耳%以上,更佳為包含85莫耳%以上,進而佳為包含90莫耳%以上,最佳為包含95莫耳%以上。
(a)的樹脂中的酸性官能基的濃度為3.4mol/kg以上,較佳為3.5mol/kg以上,更佳為4.0mol/kg以上,最佳為4.3mol/kg以上。藉由提高(a)的樹脂中的酸性官能基的濃度,水溶液的長期的穩定性提高。另外,於樹脂組成物包含後述的填料的情況下,樹脂與填料的相互作用提高,樹脂組成物內的填料的分散性或作為黏合劑的黏結性提高。藉此,由樹脂組成物製作的塗膜的厚度均勻性或耐化學品性提高。(a)的樹脂中的酸性官能基的濃度的上限值並無特別限制,但較佳為6.0mol/kg以下。
此處所謂酸性官能基的濃度,是(a)的每1kg樹脂中所含的酸性官能基的莫耳數,如以下般算出。將(a)的樹脂中的重複單元中的酸性官能基的個數設為A(個),將該重複單元的分子量設為B。
關於A、B,例如於下述重複單元的情況下,成為A=2、B=548。
另外,於下述重複單元的情況下,成為A=2、B=851。
官能基濃度是藉由A/B×1000來算出。
另外,於(a)的樹脂為具有多個重複單元的共聚物的情況下,將各重複單元的官能基濃度乘莫耳比而得者的總和設為(a)的樹脂的官能基濃度。例如,於下述結構中n/(n+m)=0.7的情況下,A=2×0.7=1.4、B=548×0.7+382×0.3=498,因此官能基濃度為1.4/498×1000=2.81。
進而,就水溶液的長期穩定性變得更高的觀點,以及樹脂組成物包含後述的填料的情況下,樹脂與填料的相互作用進一步提高、樹脂組成物內的填料的分散性或作為黏合劑的黏結性進一步提高
的觀點而言,(a)的樹脂較佳為包含下述通式(1)所表示的結構作為重複單元。
通式(1)中,R1表示碳數2~50的二價有機基,包含酚性羥基、羧基及磺酸基中的至少一種。R2表示碳數2~50的四價的有機基。
包含通式(1)所表示的結構作為重複單元的樹脂例如是使結構中包含酚性羥基、羧基及磺酸基中的至少一種的二胺與四羧酸或其衍生物進行反應而獲得。
於樹脂組成物包含後述的填料的情況下,就樹脂與填料的相互作用進一步提高、樹脂組成物內的填料的分散性或作為黏合劑的黏結性進一步提高的觀點而言,包含通式(1)所表示的結構作為重複單元的樹脂較佳為包含(a)的樹脂整體的60莫耳%以上,更佳為包含80莫耳%以上,進而佳為包含90莫耳%以上,最佳為包含95莫耳%以上。
樹脂中的通式(1)所表示的結構單元的含量可利用以下的
方法來估算。其中之一為利用紅外分光法(FT-IR)、核磁共振(NMR)、熱重量測定-質量分析(TG-MS)、飛行時間型二次離子質量分析法(TOF-SIMS)等對樹脂進行分析的方法。另一方法為將樹脂分解為各構成成分後利用氣相層析法(GC)、高效液相層析法(HPLC)、質量分析(MS)、FT-IR、NMR等來進行分析的方法。又一方法為於高溫下將樹脂灰化後利用元素分析等來進行分析的方法。
特別是本發明中,將樹脂分解為各構成成分後將高效液相層析法(HPLC)與質量分析(MS)加以組合來進行分析。
(二胺殘基)
通式(1)中,R1表示於結構中包含酚性羥基、羧基及磺酸基中的至少一種的二胺殘基。提供所述二胺殘基的較佳的二胺的具體例如所述般。
就水溶液的長期穩定性的觀點而言,(a)的樹脂中所含的通式(1)所表示的結構的總數中,R1較佳為包含20莫耳%以上的具有芳香族骨架的結構者。即,(a)的樹脂中的R1的20莫耳%以上較佳為芳香族二胺殘基。更佳為50莫耳%以上,進而佳為70莫耳%以上,最佳為90莫耳%以上。
另外,就水溶液的長期穩定性的觀點而言,R1更佳為下述通式(2)及通式(3)的至少一者。
R15表示鹵素原子或碳數1~8的一價有機基。s表示0~3的整數。t表示1或2的整數。
R16及R17分別獨立地表示鹵素原子或碳數1~8的一價有機基。u及v分別獨立地表示0~3的整數。w及x分別獨立地表示1或2的整數。R18為單鍵、O、S、NH、SO2、CO或碳數1~3的二價有機基。
作為碳數1~3的二價有機基的較佳的具體例,可列舉碳數1~3的飽和烴基等。
於樹脂組成物包含後述的填料的情況下,就樹脂與填料的相互作用進一步提高、樹脂組成物內的填料的分散性或作為黏合劑的黏結性進一步提高的觀點而言,s較佳為0。
於樹脂組成物包含後述的填料的情況下,就樹脂與填料的
相互作用進一步提高、樹脂組成物內的填料的分散性或作為黏合劑的黏結性進一步提高的觀點而言,u及v較佳為0。
作為提供通式(2)或通式(3)所表示的二胺殘基的二胺,可列舉:3,5-二胺基苯甲酸、3,4-二胺基苯甲酸、3,3'-二羧基-4,4'-二胺基二苯基甲烷、4,4'-二羧基-3,3'-二胺基二苯基甲烷、雙(3-胺基-5-羧基苯基)甲烷、雙(3-胺基-4-羧基苯基)碸、2,2-雙(3-胺基-4-羧基苯基)丙烷、2,2-雙(3-胺基-5-羧基苯基)丙烷、2,2-雙(4-胺基-3-羧基苯基)丙烷、2,2-雙(3-胺基-4-羧基苯基)六氟丙烷、2,2-雙(3-胺基-5-羧基苯基)六氟丙烷、2,2-雙(4-胺基-3-羧基苯基)六氟丙烷、雙(3-胺基-4-羧基苯基)醚等。
另外,於不損及水溶液的長期穩定性的範圍內,亦可於所述結構中包含所述其他二胺殘基。其他二胺殘基的較佳的含量為(a)的樹脂中的R1中的40莫耳%以下,更佳為30莫耳%以下,進而佳為25莫耳%以下,最佳為10莫耳%以下。
於組成物包含後述的填料的情況下,就樹脂與填料的相互作用提高,樹脂組成物內的填料的分散性提高,耐化學品性提高的觀點而言,特佳為R1的1莫耳%~25莫耳%為下述通式(4)及通式(5)的至少一者。
R19表示鹵素原子或碳數1~8的一價有機基。k表示0~4的整數。
於樹脂組成物包含後述的填料的情況下,就樹脂與填料的相互作用進一步提高、樹脂組成物內的填料的分散性或作為黏合劑的黏結性進一步提高的觀點而言,k較佳為0。
R20及R21分別獨立地表示鹵素原子或碳數1~8的一價有機基。l及m分別獨立地表示0~4的整數。R22為單鍵、O、S、NH、SO2、CO或碳數1~3的二價有機基。
作為碳數1~3的二價有機基的較佳的具體例,可列舉碳數1~3的飽和烴基等。
於樹脂組成物包含後述的填料的情況下,就樹脂與填料的相互作用進一步提高、樹脂組成物內的填料的分散性或作為黏合劑的
黏結性進一步提高的觀點而言,l及m較佳為0。
作為提供該些二胺殘基的原料,除二胺以外,亦可使用於二胺殘基的結構上代替胺基而鍵結有異氰酸酯基的二異氰酸酯化合物、或二胺的胺基的兩個氫原子取代為三甲基矽烷基而成的四-三甲基矽烷基化二胺。
進而,為了提高與基材的密接性,(a)的樹脂中的R1的1莫耳%~10莫耳%亦可為包含矽氧烷鍵的二胺殘基。作為提供包含矽氧烷鍵的二胺殘基的具體的二胺,可列舉1,3-雙(3-胺基丙基)四甲基二矽氧烷等。
於組成物包含後述的填料的情況下,就樹脂與填料的相互作用提高、樹脂組成物內的填料的分散性提高、由樹脂組成物製作的膜的厚度均勻性提高的觀點而言,R1的0.1莫耳%~10莫耳%較佳為下述通式(6)。
R24表示氫原子或甲基。p及q分別獨立地表示0以上的整數,1<p+q<20。
於樹脂組成物包含後述的填料的情況下,就樹脂與填料的相互
作用進一步提高、樹脂組成物內的填料的分散性或作為黏合劑的黏結性進一步提高的觀點而言,更佳為R24為氫原子且p=0,進一步進而佳為1<q<4。
(酸殘基)
通式(1)中,R2表示四羧酸殘基(以下,稱為「酸殘基」)。提供酸殘基的較佳的四羧酸或其衍生物的例子如所述般。
另外,亦可使用基於上文例示的四羧酸的羧酸殘基的氫原子經羥基、胺基、磺酸基、磺酸醯胺基或磺酸酯基取代1個~4個而成者。
酸殘基較佳為選自下述結構中的至少一個。即,R2較佳為選自下述結構中的至少一個。其中更佳為脂肪族結構者。
R3及R4分別獨立地表示鹵素原子或碳數1~6的有機基。R5~R14分別獨立地表示氫原子、鹵素原子或碳數1~6的有機基。a1為0~2的整數。a2為0~4的整數。a3及a4分別獨立地為0~4的整
數,a3+a4<5。a6為0~6的整數。a5及a7分別獨立地為0~2的整數。
作為R3及R4的較佳的具體例,可列舉:氯原子、氟原子、碳數1~4的飽和烴基、碳數4~6的環狀飽和烴基、三氟甲基等。
作為R5~R14的較佳的具體例,可列舉:氫原子、氯原子、氟原子、碳數1~4的飽和烴基、碳數4~6的環狀飽和烴基、三氟甲基等。於樹脂組成物包含後述的填料的情況下,就樹脂與填料的相互作用進一步提高、樹脂組成物內的填料的分散性或作為黏合劑的黏結性進一步提高的觀點而言,R5~R14更佳為氫原子。
另外,就同樣的觀點而言,a1及a2較佳為0,且較佳為a3+a4<2,a6較佳為0~2,更佳為0,a5及a7較佳為0~1,更佳為0。
藉由使用該些酸殘基,不僅水溶液的長期的穩定性提高,而且於樹脂組成物包含後述的填料的情況下,樹脂與填料的相互作用提高、樹脂組成物內的填料的分散性提高。藉此,由樹脂組成物製作的膜的厚度均勻性或耐化學品性提高。
就獲得所述效果的方面而言,最佳的酸殘基為下述結構。
進而,視需要亦可使用1,3-雙(對羧基苯基)-1,1,3,3-四甲基二矽氧烷、1-(對羧基苯基)-3-鄰苯二甲酸-1,1,3,3-四甲基二矽氧烷、1,3-雙鄰苯二甲酸-1,1,3,3-四甲基二矽氧烷等具有矽氧烷鍵的羧基化合物。藉由含有源自具有矽氧烷鍵的羧基化合物的酸殘基,可提高由樹脂組成物製作的膜對基板的接著性。
(封端劑)
就水溶液的穩定性、填料的分散性的觀點而言,包含通式(1)所表示的結構作為重複單元的樹脂的末端骨架較佳為包含選自下述通式(7)、通式(8)及通式(9)所表示的結構中的至少一種。
R25、R26及R27分別獨立地表示碳數4~30的一價有機基,包含酚性羥基、羧基及磺酸基中的至少一種。
該些結構可藉由利用酸酐、單羧酸、及單胺化合物等封端劑將樹脂的末端密封來導入。
通式(7)中,R25表示酸酐的殘基。作為酸酐的具體例,可列舉3-羥基鄰苯二甲酸酐等。
通式(8)中,R26表示單羧酸的殘基。作為單羧酸的具體
例,可列舉:2-羧基苯酚、3-羧基苯酚、4-羧基苯酚、2-羧基苯硫酚、3-羧基苯硫酚、4-羧基苯硫酚、1-羥基-8-羧基萘、1-羥基-7-羧基萘、1-羥基-6-羧基萘、1-羥基-5-羧基萘、1-羥基-4-羧基萘、1-羥基-3-羧基萘、1-羥基-2-羧基萘、1-巰基-8-羧基萘、1-巰基-7-羧基萘、1-巰基-6-羧基萘、1-巰基-5-羧基萘、1-巰基-4-羧基萘、1-巰基-3-羧基萘、1-巰基-2-羧基萘、2-羧基苯磺酸、3-羧基苯磺酸、4-羧基苯磺酸等。
通式(9)中,R27表示單胺的殘基。作為單胺的具體例,可列舉:3-胺基-4,6-二羥基嘧啶、2-胺基苯酚、3-胺基苯酚、4-胺基苯酚、5-胺基-8-羥基喹啉、4-胺基-8-羥基喹啉、1-羥基-8-胺基萘、1-羥基-7-胺基萘、1-羥基-6-胺基萘、1-羥基-5-胺基萘、1-羥基-4-胺基萘、1-羥基-3-胺基萘、1-羥基-2-胺基萘、1-胺基-7-羥基萘、2-羥基-7-胺基萘、2-羥基-6-胺基萘、2-羥基-5-胺基萘、2-羥基-4-胺基萘、2-羥基-3-胺基萘、1-胺基-2-羥基萘、1-羧基-8-胺基萘、1-羧基-7-胺基萘、1-羧基-6-胺基萘、1-羧基-5-胺基萘、1-羧基-4-胺基萘、1-羧基-3-胺基萘、1-羧基-2-胺基萘、1-胺基-7-羧基萘、2-羧基-7-胺基萘、2-羧基-6-胺基萘、2-羧基-5-胺基萘、2-羧基-4-胺基萘、2-羧基-3-胺基萘、1-胺基-2-羧基萘、2-胺基菸鹼酸、4-胺基菸鹼酸、5-胺基菸鹼酸、6-胺基菸鹼酸、4-胺基水楊酸、5-胺基水楊酸、6-胺基水楊酸、3-胺基-鄰甲苯甲酸、三聚氰酸一醯胺(ammelide)、2-胺基苯甲酸、3-胺基苯甲酸、4-胺基苯甲酸、2-胺基苯磺酸、3-胺基苯磺酸、4-胺基苯磺酸等、5-胺基-8-巰基喹啉、4-胺基-8-巰基喹啉、1-巰
基-8-胺基萘、1-巰基-7-胺基萘、1-巰基-6-胺基萘、1-巰基-5-胺基萘、1-巰基-4-胺基萘、1-巰基-3-胺基萘、1-巰基-2-胺基萘、1-胺基-7-巰基萘、2-巰基-7-胺基萘、2-巰基-6-胺基萘、2-巰基-5-胺基萘、2-巰基-4-胺基萘、2-巰基-3-胺基萘、1-胺基-2-巰基萘、3-胺基-4,6-二巰基嘧啶、2-胺基苯硫酚、3-胺基苯硫酚、4-胺基苯硫酚等。
該些酸酐、單羧酸、及單胺化合物等封端劑可單獨使用或組合兩種以上來使用。另外,亦可併用該些以外的封端劑。
(a)的樹脂中的所述封端劑的含量較佳為構成羧酸殘基及胺殘基的成分單體的添加莫耳數的0.1莫耳%~60莫耳%的範圍,更佳為5莫耳%~50莫耳%。藉由設為此種範圍,可獲得塗佈時的溶液的黏性適度,且具有優異的膜物性的樹脂組成物。
與通常的縮聚反應同樣地,二胺與酸的添加比率(莫耳比)越接近1:1,所生成的聚合體的聚合度越大,重量平均分子量越增加。本發明中,(a)的樹脂的重量平均分子量較佳為10,000以上且150,000以下。重量平均分子量是藉由凝膠滲透層析法(GPC)而測定、並以聚苯乙烯換算而求出的值。以下記載GPC的測定條件。
1)機器裝置:沃特斯(Waters)2690
2)管柱:東曹股份有限公司(TOSOH CORPORATION),TSK-GEL(d-4000 & d-2500)
3)溶媒:NMP
4)流速:0.4mL/min
5)試樣濃度:0.05wt%~0.1wt%
6)注入量:50μL
7)溫度:40℃
8)檢測器:沃特斯(Waters)996
再者,用於換算的聚苯乙烯中使用聚合物實驗室(Polymer Laboratories)公司的標準聚苯乙烯。
藉由將(a)的樹脂的重量平均分子量設為10,000以上,可保持作為黏合劑而言充分的黏結性。另一方面,藉由將(a)的樹脂的重量平均分子量設為150,000以下,可維持於溶媒中的高的溶解性。於獲得具有所述重量平均分子量的聚合體時,二胺與酸的添加比率(莫耳比)較佳為100:50~150。
作為所述縮聚反應中所使用的溶媒,只要為溶解有所生成的樹脂者,則並無特別限定,可較佳地使用N-甲基-2-吡咯啶醚、N-甲基己內醯胺、N,N-二甲基乙醯胺、N,N-二甲基甲醯胺、二甲基亞碸、γ-丁內酯、二甲基咪唑啉等非質子性極性溶媒、苯酚、間甲酚、氯苯酚、硝基苯酚等酚系溶媒、多磷酸、於磷酸加入五氧化二磷而成的磷系溶媒等。
一般而言,於該些溶媒中使酸酐或二羧酸二酯體與二胺或二異氰酸酯於150℃以上的溫度下進行反應,藉此獲得聚醯亞胺聚合體。另外,為了促進反應,可添加三乙胺、吡啶等鹼類作為觸媒。之後,投入至水等中而使樹脂析出並進行乾燥,藉此可以固體的形式獲得聚合體。
((b)鹼性化合物)
藉由本發明的實施形態的樹脂組成物包含(b)鹼性化合物,(a)的樹脂中所含的酚性羥基、羧基或磺酸基與(b)鹼性化合物形成鹽,樹脂組成物相對於水的溶解性及分散穩定性得到提高。
作為(b)鹼性化合物,可列舉鹼金屬及鹼土金屬的氫氧化物或碳酸鹽、有機胺類等。特別是就進一步提高由樹脂組成物製作的塗膜的強度及耐化學品性的觀點而言,較佳為包含選自鹼金屬中的至少一元素的化合物。
作為鹼金屬的氫氧化物的例子,可列舉:氫氧化鋰、氫氧化鈉、氫氧化鉀、氫氧化銣及氫氧化銫等。可含有兩種以上的該些化合物。就提高樹脂組成物相對於水的溶解性及分散穩定性的觀點而言,較佳為氫氧化鋰、氫氧化鈉及氫氧化鉀。
作為鹼金屬的碳酸鹽的例子,可列舉:碳酸鋰、碳酸氫鋰、碳酸鈉、碳酸氫鈉、碳酸鉀、碳酸氫鉀、碳酸氫銣、碳酸銫、碳酸氫銫及碳酸鈉鉀等。可含有兩種以上的該些化合物。就樹脂組成物相對於水的溶解性及分散穩定性等觀點而言,較佳為碳酸鈉、碳酸氫鈉、碳酸鉀、碳酸氫鉀及碳酸鈉鉀,更佳為碳酸鈉及碳酸氫鈉。
作為有機胺類,可列舉:三甲胺、三乙胺、三異丙胺、三丁胺、三乙醇胺、N-甲基乙醇胺等脂肪族三級胺、或吡啶、N,N-二甲基胺基吡啶、二甲基吡啶等芳香族胺、四甲基氫氧化銨、四乙基氫氧化銨等四級銨鹽等。可使用兩種以上的該些化合物。
所述中,(b)鹼性化合物特佳為碳酸鈉及氫氧化鈉。
就可充分地溶解樹脂的方面而言,相對於(a)的樹脂中的酸性官能基100莫耳%,樹脂組成物中的(b)鹼性化合物的含量較佳為20莫耳%以上,更佳為50莫耳%以上。另外,就可防止樹脂的分解或製成塗膜時的裂紋的產生的方面而言,較佳為450莫耳%以下,更佳為400莫耳%以下,進而佳為300莫耳%以下,最佳為250莫耳%以下。
本發明的實施形態的樹脂組成物較佳為以固體成分濃度15質量%溶解於水中時的pH為4~12。
若脫離該範圍,則樹脂組成物含有後述的填料時的填料的分散性惡化,由樹脂組成物製作的塗膜的厚度均勻性、強度及耐化學品性下降。就進一步提高所述特性的觀點而言,樹脂組成物的pH的較佳的範圍為5以上且10以下。
關於pH值,設為如下情況下的值:使包含(a)含有聚醯亞胺、聚醯胺醯亞胺及聚苯并噁唑中的至少一種,且於側鏈具有酚性羥基、羧基及磺酸基中的至少一種酸性官能基,該酸性官能基的濃度為3.4mol/kg以上的樹脂、與(b)鹼性化合物的樹脂組成物以濃度15質量%溶解於水中而得的值;或使自電池的構件完全萃取出的包含(a)含有聚醯亞胺、聚醯胺醯亞胺及聚苯并噁唑中的至少一種,且於側鏈具有酚性羥基、羧基及磺酸基中的至少一種酸性官能基,該酸性官能基的濃度為3.4mol/kg以上的樹脂、與(b)鹼性化合物的樹脂組成物以濃度15質量%溶解於水中而得的值。
((c)水)
本發明的實施形態的樹脂組成物包含(c)水作為溶媒。就水溶液的穩定性的觀點而言,溶媒中的(c)水較佳為佔樹脂組成物中所含的溶媒中的80質量%以上。更佳為90質量%以上,最佳為99質量%以上。
本發明的實施形態的樹脂組成物較佳為相對於(a)的樹脂100質量份而含有50質量份~1,000,000質量份的(c)水。一般而言,就塗佈性的觀點而言,相對於(a)的樹脂100質量份,就可抑制凝膠化的方面而言,(c)水較佳為50質量份以上,更佳為100質量份以上。另外,就可抑制分解的方面而言,相對於(a)的樹脂100質量份,(c)水較佳為100,000質量份以下,更佳為3,000質量份以下。
另外,就作業性的觀點而言,本發明的實施形態的樹脂組成物的黏度較佳為於25℃下為1mPa.s~100mPa.s的範圍內。
本發明的實施形態的樹脂組成物的pH較佳為4~12。若脫離該範圍,則樹脂組成物含有後述的填料時的填料的分散性惡化,由樹脂組成物製作的塗膜的厚度均勻性、強度及耐化學品性下降。就進一步提高所述特性的觀點而言,樹脂組成物的pH的較佳的範圍為5以上且10以下。
本發明的pH為使用pH計(LAQUA F-71,堀場製作所製造)而測定的值。pH的校正是使用JIS Z 8802(2011)「pH測定方法」中所確定中的下述5種標準液(pH為2、4、7、9、12)來進行。
○pH2標準液(草酸鹽)
0.05mol/L四草酸鉀水溶液
○pH4標準液(鄰苯二甲酸鹽)
0.05mol/L鄰苯二甲酸氫鉀水溶液
○pH7標準液(中性磷酸鹽:下述兩種水溶液的混合液)
0.025mol/L磷酸二氫鉀水溶液
0.025mol/L磷酸氫二鈉水溶液
○pH9標準液(硼酸鹽)
0.01mol/L四硼酸鈉(硼砂)水溶液
○pH12標準液
飽和氫氧化鈣水溶液。
就進一步提高塗佈性的觀點而言,本發明的實施形態的樹脂組成物亦可含有界面活性劑等。另外,亦可含有乙醇或異丙醇等低級醇、乙二醇或丙二醇等多元醇等有機溶媒。樹脂組成物中的有機溶媒的含量較佳為樹脂組成物整體的50質量%以下,更佳為10質量%以下。
製成本發明的實施形態的樹脂組成物時的方法並無特別限制,就安全性的觀點而言,較佳為使規定量的鹼性化合物溶解於水中後使樹脂粉末逐次少量溶解。於中和反應慢的情況下,亦可於30℃~110℃左右的水浴或油浴中進行加溫,亦可進行超音波處理。亦可於溶解後進而加入水或加以濃縮而調整為規定的黏度。
((d)填料)
本發明的實施形態的樹脂組成物亦可含有(d)填料。藉由樹脂組成物含有(d)填料,由樹脂組成物製作的膜的機械強度或耐熱性提高。進而藉由使用導電性粒子或高折射填料或者低折射填料作為(d)填料,亦可將樹脂組成物用於電子材料或光學材料中。含有(d)填料的樹脂組成物亦可為漿料狀。
作為(d)填料的較佳的例子,可列舉包含碳、錳、鋁、鋇、鈷、鎳、鐵、矽、鈦、錫、及鍺中的至少一種原子的化合物。該些化合物發揮作為電極活性物質、強度增強材料、導熱物質或高介電物質的作用。因此,本發明的實施形態的樹脂組成物含有填料,並製成漿料狀,藉此可用作電子零件、二次電池、電雙層電容器等功能構件用漿料。
作為二次電池或電雙層電容器的正極用的填料的例子,可列舉:磷酸鐵鋰、鈷酸鋰、鎳酸鋰、錳酸鋰、活性炭及碳奈米管等。
作為二次電池或電雙層電容器的負極用的填料的例子,可列舉:矽、氧化矽、碳化矽、錫、氧化錫、鍺、鈦酸鋰、硬碳、軟碳、活性炭及碳奈米管等。特別是將矽、錫、或鍺用作活性物質的蓄電池於充電時活性物質的體積膨脹大,因此就防止活性物質的微粉化的方面而言,較佳為將(a)的樹脂之類的機械強度高的樹脂用作黏合劑。另外,於填料為鈦酸鋰的情況下,可獲得速率特性優異的二次電池或電雙層電容器。
作為負極用的填料的例子而特佳為包含矽、氧化矽、鈦酸鋰、碳化矽、該些中的兩個以上的混合體、該些中的一個或兩個以上
的混合體與碳的混合體、及該些中的一個或兩個以上的混合體的表面經碳塗佈而成者中的至少一種的填料。該些活性物質中(a)的樹脂的黏結性特別強,可獲得電容維持率高的二次電池或電雙層電容器。
就可提高由樹脂組成物獲得的膜的機械強度或耐熱性的方面而言,相對於(a)的樹脂100質量份,本發明的實施形態的樹脂組成物中的(d)填料的含量較佳為0.01質量份以上,更佳為0.1質量份以上。另外,就可維持樹脂組成物的塗膜強度的方面而言,較佳為100,000質量份以下,更佳為10,000質量份以下。
漿料例如可藉由向使樹脂溶解或分散於水或溶劑中而成者中添加填料與視需要的其他成分,並均勻地混合而獲得。混合可列舉使用行星式混合機、自轉公轉式混合機、三輥機、球磨機、機械攪拌器、薄膜旋回型混合機等的方法。
<積層體>
本發明的實施形態的積層體於基材的至少單面上具有由所述樹脂組成物製膜而成的層。該積層體例如可藉由將樹脂組成物塗佈於基材的單面或兩面並加以乾燥而獲得。
作為基材,可較佳地使用銅箔、鋁箔、不鏽鋼箔等金屬箔或矽基板、玻璃基板、塑膠膜等。作為塗佈方法,可列舉使用輥塗機、縫模塗佈機、棒塗機、缺角輪塗佈機、旋塗機等的方法。就完全去除水的方面而言,乾燥溫度較佳為30℃以上,更佳為50℃以上。另外,就防止電極的裂紋的觀點而言,較佳為500℃以下,更佳為200℃以下。
另外,本發明的實施形態的樹脂組成物於用作電極用漿料的情況下,亦可含有乙炔黑、科琴黑、碳奈米管等導電助劑。藉由含有導電助劑,可提高充放電速率。就兼顧導電性與電容的方面而言,相對於活性物質100質量份,導電助劑的含量較佳為0.1質量份~20質量份。
另外,為了調整黏度,本發明的實施形態的樹脂組成物亦可含有羧基甲基纖維素的鈉鹽。就於二次電池或電雙層電容器中具有高的電容維持率的觀點而言,相對於活性物質100質量份,其含量較佳為50質量份以下。
藉由將樹脂組成物或含有填料的樹脂組成物塗佈於基材的至少單面上及加以乾燥並製膜,從而製成積層體。作為基材,可列舉絕緣性基材、導電性基材等,於用作電子元件的情況下,較佳為導電性基材或具有導電性配線的絕緣基材。特別是二次電池或電雙層電容器的電極可藉由將含有電極活性物質作為填料的樹脂組成物塗佈於銅箔、鋁箔、不鏽鋼箔等集電體的單面或兩面並加以乾燥而獲得。關於以所述方式獲得的正極及負極,將經由間隔件積層多個而成者與電解液一起放入金屬殼體等外裝材料中,並進行密封,藉此可獲得二次電池或電雙層電容器等蓄電元件。
作為間隔件的例子,可列舉聚乙烯、聚丙烯等聚烯烴、纖維素、聚苯硫醚、芳族聚醯胺、或聚醯亞胺等原材料形成的微多孔膜或不織布等。
作為電解液的溶劑,可使用丙二醇碳酸酯、乙二醇碳酸
酯、碳酸二甲酯、碳酸乙基甲酯、碳酸乙烯酯等碳酸酯系化合物、或乙腈、環丁碸、γ-丁內酯等。可使用兩種以上的該些化合物。
作為電解質的例子,可列舉:六氟磷酸鋰、氟硼酸鋰、過氯酸鋰等鋰鹽、四乙基銨四氟硼酸鹽、三乙基甲基銨四氟硼酸鹽等銨鹽等。
[實施例]
以下列舉實施例以更詳細地說明本發明,但本發明不受該些實施例的任何限制。各實施例及比較例中的樹脂的官能基濃度計算、重量平均分子量測定、水溶液的pH測定、水溶液穩定性、由使用該些的漿料製作的膜的特性評價、以及電池特性評價是利用以下的方法進行。
<官能基濃度計算方法>
依據所述「實施方式」欄中說明的算出方法,求出(a)的樹脂的重複單元中的酸性官能基的個數A及該重複單元的分子量B,以A/B×1000的形式算出官能基濃度(mol/kg)。
<樹脂的重量平均分子量測定>
樹脂A~樹脂N的分子量是利用凝膠滲透層析法(GPC)進行測定,並藉由聚苯乙烯換算來計算重量平均分子量(Mw)。以下記載GPC測定條件。
1)機器裝置:沃特斯(Waters)2690
2)管柱:東曹股份有限公司(TOSOH CORPORATION),TSK-GEL(d-4000 & d-2500)
3)溶媒:NMP
4)流速:0.4mL/min
5)試樣濃度:0.05wt%~0.1wt%
6)注入量:50μL
7)溫度:40℃
8)檢測器:沃特斯(Waters)996
再者,用於換算的聚苯乙烯中使用聚合物實驗室(Polymer Laboratories)公司的標準聚苯乙烯。
<水溶液的pH測定>
採集少量的水溶液1~水溶液21,利用pH計(LAQUA F-71,堀場製作所製造)來測定水溶液的pH。pH的校正是使用JIS Z 8802(2011)「pH測定方法」中所確定中的下述5種標準液(pH為2、4、7、9、12)來進行。
○pH2標準液(草酸鹽)
0.05mol/L四草酸鉀水溶液
○pH4標準液(鄰苯二甲酸鹽)
0.05mol/L鄰苯二甲酸氫鉀水溶液
○pH7標準液(中性磷酸鹽:下述兩種水溶液的混合液)
0.025mol/L磷酸二氫鉀水溶液
0.025mol/L磷酸氫二鈉水溶液
○pH9標準液(硼酸鹽)
0.01mol/L四硼酸鈉(硼砂)水溶液
○pH12標準液
飽和氫氧化鈣水溶液。
<水溶液的穩定性評價>
將水溶液1~水溶液21分別於室溫下放置1個月及3個月、以及於冷藏下放置1週及1個月後,目視觀察來確認水溶液的穩定性。將均未看到析出、凝膠化者記載為良,對存在任一變化者記載所產生的變化。將於室溫下放置一個月而佳者設為合格,將於室溫下放置一個月而存在任一變化者設為不合格。
<膜的特性評價(分散性、黏結性的評價)>
為了觀察填料的分散性、作為黏合劑的黏結性,進行具有填料的樹脂組成物的膜特性評價。若填料的分散性、作為黏合劑的黏結性差,則產生由填料的凝聚導致的膜厚的均勻性的惡化,或於膜產生裂紋。
將合成例19中獲得的鋰離子電池用負極活性物質80質量份、水溶液1~水溶液21(固體成分濃度15質量%)100質量份、作為導電助劑的乙炔黑5質量份、水15質量份混合分散,獲得固體成分50質量%的漿料。
對該漿料於鋁箔上利用棒塗機,以熱處理後的膜厚的平均值成為25μm的方式調整厚度,並以寬度10cm進行塗佈。於塗佈後在50℃下乾燥30分鐘,之後花費30分鐘昇溫至150℃,於150℃下進行1小時熱處理後,冷卻至50℃以下。冷卻後藉由目視觀察膜,並確認裂紋的有無。將無裂紋者設為「良」,將可確認到裂紋者
設為「不良」。
另外,於塗佈寬度中自兩端向內側5mm的區域,在寬度方向等間隔地選擇10點,利用測微計來測定熱處理後的膜厚。測定值的最大值、最小值中與平均值(25μm)的差大的值設為T1時,以
T2=(T1-25)/25*100(%)
來算出膜厚的偏差T2,並定義為±T2%。將偏差處於-30%至+30%的範圍內者(其中,正好為±30%的情況除外)設為合格,將處於所述範圍外者設為不合格。
進而,將該膜以直徑16mm的圓形切取5片,浸漬於將碳酸二乙酯與乙二醇碳酸酯以重量比計各混合50%而成的溶液中,於40℃下放置24h、一週。放置後自溶液中取出膜並進行水洗,於50℃下乾燥1小時後,藉由目視進行觀察,確認膜的溶解的有無、裂紋的有無。將看到膜的溶解者設為「溶解」,將產生裂紋者設為「不良」,將無膜的溶解及裂紋者設為「良」。
進而,亦製作利用與所述相同的方法以熱處理後的膜厚的平均值成為50μm的方式調整厚度而成者,以直徑16mm的圓形切取5片,浸漬於將碳酸二乙酯與乙二醇碳酸酯以重量比計各混合50%而成的溶液中,於40℃下放置一週。放置後自溶液中取出膜並進行水洗,於50℃下乾燥1小時後,藉由目視進行觀察,確認膜的溶解的有無、裂紋的有無。將看到膜的溶解者設為「溶解」,將產生裂紋者設為「不良」,將無膜的溶解及裂紋者設為「良」。
<電池特性評價>
(1)負極的製作
使用<膜的特性評價(分散性、黏結性的評價)>中製作的固體成分50%的漿料,於電解銅箔上使用棒塗機,以150℃下的熱處理後的膜厚成為25μm的方式調整厚度,並進行塗佈,於塗佈後在110℃下乾燥30分鐘。於乾燥後將塗佈部衝壓為直徑16mm的圓形,於150℃下進行24小時的真空乾燥,從而製成負極。
(2)電池特性評價
於測定充放電特性後使用HS單元(寶泉(股)製造),於氮氣環境下進行鋰離子電池的組裝。間隔件是使用以直徑24mm對聚乙烯多孔質膜(寶泉(股)製造)進行衝壓而成者。正極是使用以直徑16mm對在鋁箔上將鈷酸鋰製的活性物質煆燒而成者(寶泉(股)製造)進行衝壓而成者。依序重疊負極、間隔件及正極,並注入1mL的作為電解液的MIRET1(三井化學(股)製造)後封入,從而獲得鋰離子電池。
對如所述般製作的鋰離子電池進行充放電。充放電是以6mA的定電流充電至電池電壓為4.2V為止,進而於4.2V的定電壓下自充電開始充電至達到共計2小時30分鐘為止後,休止30分鐘,並以6mA的定電流進行放電至電池電壓為2.7V,將所述設為一循環。之後,於同樣的條件下重複進行49次充放電,對共計50循環測定各循環的充電電容及放電電容。而且,依據以下的式子來算出電容維持率。
電容維持率(%)=(第50循環的放電電容/第1循環的放電電容)×100
合成例1:樹脂A的合成
於充分乾燥的四口燒瓶中,一面於氮氣環境下攪拌,一面於室溫下使29.84g(100mmol)的3,3'-二羧基-4,4'-亞甲基雙(環己基胺)(東京化成工業(股)製造,以下為CMCHA)溶解於131.79g的NMP中。之後,添加31.02g(100mmol)的3,3',4,4'-二苯基醚四羧酸二酐(東京化成工業(股)製造,以下為ODPA)、15.00g的NMP,於40℃下進行1小時聚合反應,繼而一面將反應中產生的水餾去,一面於200℃下進行6小時聚合反應。於反應結束後降溫至室溫,將該溶液投入至3L的水中,並過濾分離所獲得的沈澱,利用1.5L的水清洗3次。使清洗後的固體於50℃的通風烘箱中乾燥3天,從而獲得樹脂A的固體。樹脂A的重量平均分子量為30000。
合成例2:樹脂B的合成
代替29.84g(100mmol)的CMCHA,使用20.89g(70mmol)的CMCHA及8.59g(30mmol)的3,3'-二羧基-4,4'-二胺基二苯基甲烷(和歌山精化工業(股)製造,商品名「MBAA」),除此以外與合成例1同樣地進行而獲得樹脂B的固體。樹脂B的重量平均分子量為32000。
合成例3:樹脂C的合成
代替29.84g(100mmol)的CMCHA,使用28.63g(100mmol)的MBAA,除此以外與合成例1同樣地進行而獲得樹脂C的固體。樹脂C的重量平均分子量為35000。
合成例4:樹脂D的合成
於充分乾燥的四口燒瓶中,一面於氮氣環境下攪拌,一面於室溫下使28.63g(100mmol)的MBAA溶解於131.79g的NMP中。之後,添加30.00g(100mmol)的1,3,3a,4,5,9b-六氫-5(四氫-2,5-二氧代-3-呋喃基)萘并[1,2-c]呋喃-1,3-二酮(新日本理化(股)製造,商品名「理家德(Rikacid)TDA-100」)、15.00g的NMP,於40℃下進行1小時聚合反應,繼而一面將反應中產生的水餾去,一面於200℃下進行6小時聚合反應。於反應結束後降溫至室溫,將該溶液投入至3L的水中,並過濾分離所獲得的沈澱,利用1.5L的水清洗3次。使清洗後的固體於50℃的通風烘箱中乾燥3天,從而獲得樹脂D的固體。樹脂D的重量平均分子量為18000。
合成例5:樹脂E的合成
代替30.00g(100mmol)的TDA-100,使用24.82g(100mmol)的雙環[2,2,2]辛-7-烯-2,3,5,6-四羧酸二酐(東京化成工業(股)製造,以下為BOE),除此以外與合成例4同樣地進行而獲得樹脂E的固體。樹脂E的重量平均分子量為15000。
合成例6:樹脂F的合成
代替30.00g(100mmol)的TDA-100,使用22.42g(100mmol)的3-(羧基甲基)-1,2,4-環戊烷三羧酸1,4:2,3-二酐(東京化
成工業(股)製造,以下為JPDA),除此以外與合成例4同樣地進行而獲得樹脂F的固體。樹脂F的重量平均分子量為20000。
合成例7:樹脂G的合成
代替30.00g(100mmol)的TDA-100,使用21.81g(100mmol)的均苯四甲酸二酐(大賽璐工業(股)製造,商品名「PMDA」),除此以外與合成例4同樣地進行而獲得樹脂G的固體。樹脂G的重量平均分子量為28000。
合成例8:樹脂H的合成
代替30.00g(100mmol)的TDA-100,使用21.01g(100mmol)的1,2,3,4-環戊烷四羧酸二酐(東京化成工業(股)製造,以下為CPDA),除此以外與合成例4同樣地進行而獲得樹脂H的固體。樹脂H的重量平均分子量為16000。
合成例9:樹脂I的合成
代替30.00g(100mmol)的TDA-100,使用19.61g(100mmol)的1,2,3,4-環丁烷四羧酸二酐(東京化成工業(股)製造,以下為CBDA),除此以外與合成例4同樣地進行而獲得樹脂I的固體。樹脂I的重量平均分子量為25000。
合成例10:樹脂J的合成
代替30.00g(100mmol)的TDA-100,使用19.81g(100mmol)的1,2,3,4-丁烷四羧酸二酐(和光化學(Wako Chemical)(股)製造,以下為BTA),除此以外與合成例4同樣地進行而獲得樹脂J的固體。樹脂J的重量平均分子量為35000。
合成例11:樹脂K的合成
於充分乾燥的四口燒瓶中,一面於氮氣環境下攪拌,一面於室溫下使26.63g(93mmol)的MBAA、0.75g(3mmol)的APDS溶解於131.79g的NMP中。之後,添加19.81g(100mmol)的BTA、15.00g的NMP,於40℃下進行1h反應,繼而添加1.10g(8mmol)的4-胺基苯甲酸(東京化成工業(股)製造,以下為4ABA),進而於40℃下反應1h。繼而一面將反應中產生的水餾去,一面於200℃下進行6h聚合反應。反應結束後降溫至室溫,將該溶液投入至3L的水中,並過濾分離所獲得的沈澱,利用1.5L的水清洗3次。使清洗後的固體於50℃的通風烘箱中乾燥3天,從而獲得樹脂K的固體。樹脂K的重量平均分子量為30000。
合成例12:樹脂L的合成
代替30.00g(100mmol)的TDA-100,使用44.42g(100mmol)的2,2-雙(3,4-二羧基苯基)六氟丙烷二酐(東京化成工業(股)製造,以下為6FDA),除此以外與合成例4同樣地進行而獲得樹脂L的固體。樹脂L的重量平均分子量為65000。
合成例13:樹脂M的合成
於充分乾燥的四口燒瓶中,一面於氮氣環境下攪拌,一面於室溫下使14.44g(95mmol)的3,5-二胺基苯甲酸(東京化成工業(股)製造,以下為DAB)、1.24g(5mmol)的1,3-雙-3-胺基丙基四甲基二矽氧烷(東麗道康寧矽酮(股)製造,商品名「APDS」)溶解於131.79g的NMP中。之後添加31.02g(100mmol)的
ODPA、15.00g的NMP,於40℃下進行1h聚合反應,繼而一面將反應中產生的水餾去,一面於200℃下進行6h聚合反應。反應結束後降溫至室溫,將該溶液投入至3L的水中,並過濾分離所獲得的沈澱,利用1.5L的水清洗3次。使清洗後的固體於50℃的通風烘箱中乾燥3天,從而獲得樹脂M的固體。樹脂M的重量平均分子量為48000。
合成例14:樹脂N的合成
於充分乾燥的四口燒瓶中,一面於氮氣環境下攪拌,一面於室溫下使28.63g(100mmol)的MBAA溶解於131.79g的NMP中。之後一面將溶液的溫度保持為10℃以下,一面添加20.30g(100mmol)的間苯二甲醯氯(東京化成工業(股)製造,以下為IPC)、15.00g的NMP,於10℃以下進行1小時聚合反應,繼而於23℃下進行6小時聚合反應。反應結束後將該溶液投入至3L的水中,並過濾分離所獲得的沈澱,利用1.5L的水清洗3次。使清洗後的固體於50℃的通風烘箱中乾燥3天,從而獲得樹脂N的固體。樹脂N的重量平均分子量為30000。
將合成例1~合成例14的樹脂的組成、分子量、官能基濃度示於表1中。
合成例15:樹脂O的合成
於充分乾燥的四口燒瓶中,一面於氮氣環境下攪拌,一面於室溫下使27.20g(95mmol)的MBAA、0.54g(5mmol)的對苯二胺(東京化成工業(股)製造,以下為PDA)溶解於131.79g的
NMP中。之後添加19.81g(100mmol)的BTA、15.00g的NMP,於40℃下反應2h。繼而一面將反應中產生的水餾去,一面於200℃下進行6h聚合反應。反應結束後降溫至室溫,將該溶液投入至3L的水中,並過濾分離所獲得的沈澱,利用1.5L的水清洗3次。使清洗後的固體於50℃的通風烘箱中乾燥3天,從而獲得樹脂O的固體。樹脂O的重量平均分子量為35000。
合成例16:樹脂P的合成
於充分乾燥的四口燒瓶中,一面於氮氣環境下攪拌,一面於室溫下使27.20g(95mmol)的MBAA、0.43g(4mmol)的PDA、0.10g(1mmol)的2,2'-氧基雙(乙基胺)(東京化成工業(股)製造,以下為OBEA)溶解於131.79g的NMP中。之後添加19.81g(100mmol)的BTA、15.00g的NMP,於40℃下反應2h。繼而一面將反應中產生的水餾去,一面於200℃下進行6h聚合反應。反應結束後降溫至室溫,將該溶液投入至3L的水中,並過濾分離所獲得的沈澱,利用1.5L的水清洗3次。使清洗後的固體於50℃的通風烘箱中乾燥3天,從而獲得樹脂P的固體。樹脂P的重量平均分子量為35000。
合成例17:樹脂Q的合成
於充分乾燥的四口燒瓶中,一面於氮氣環境下攪拌,一面於室溫下使27.20g(95mmol)的MBAA、0.32g(3mmol)的PDA、0.10g(1mmol)的OBEA溶解於131.79g的NMP中。之後添加19.81g(100mmol)的BTA、15.00g的NMP,於40℃下反應
1h,進而添加0.28g(2mmol)的4ABA,進而於40℃下反應1小時。繼而一面將反應中產生的水餾去,一面於200℃下進行6h聚合反應。反應結束後降溫至室溫,將該溶液投入至3L的水中,並過濾分離所獲得的沈澱,利用1.5L的水清洗3次。使清洗後的固體於50℃的通風烘箱中乾燥3天,從而獲得樹脂Q的固體。樹脂Q的重量平均分子量為30000。
合成例18:樹脂R的合成
代替30.00g(100mmol)的TDA-100,使用26.42g(100mmol)的5-(2,5-二氧代四氫糠基)-3-甲基-3-環己烯-1,2-二羧酸酐(迪愛生(DIC)(股)製造,商品名「艾比克隆(EPICLON)B-4400」),除此以外與合成例4同樣地進行而獲得樹脂R的固體。樹脂R的重量平均分子量為20000。
合成例19:鋰離子電池用負極活性物質的合成
將50g的粒徑約10μm的天然石墨(富士石墨(股)製造,CBF1)、60g的奈米矽粉末(奧德里奇(Aldrich)公司製造)、10g的碳黑(三菱化學(股)製造,3050)混合,於球磨機中以600轉充分分散12小時,之後於80℃下真空乾燥12小時,從而獲得矽-碳的混合負極活性物質。
水溶液1~水溶液21
如表1記載般,將樹脂、鹼性化合物及水混合,製備固體成分濃度為15質量%的水溶液。將水溶液1~水溶液21的各組成及水溶液的pH值示於表2中。
實施例1~實施例17、比較例1~比較例4
評價表2中記載的水溶液的穩定性,以及評價使用由該些水溶液製作的漿料而獲得的膜的膜特性。將評價結果示於表3中。
實施例18~實施例26、比較例5~比較例7
評價使用由表2中記載的水溶液製作的漿料而獲得的膜的電池特性。將評價結果示於表4中。
比較例8
將80質量份的合成例15中獲得的鋰離子電池用負極活性物質、15質量份的聚偏二氟乙烯(岸田化學(Kishida chemical)製造,以下為PVdF)、5質量份的作為導電助劑的乙炔黑、以及100質量份的NMP混合分散,從而獲得固體成分50質量%的漿料。將使用該漿料進行的電池特性評價結果示於表4中。
Claims (21)
- 一種樹脂組成物,其包含:(a)含有聚醯亞胺的樹脂,於側鏈具有酚性羥基、羧基及磺酸基中的至少一種酸性官能基,所述酸性官能基的濃度為4.3mol/kg以上;以及(b)鹼性化合物。
- 如申請專利範圍第1項所述的樹脂組成物,其以固體成分濃度15質量%溶解於水中時的pH為4~12。
- 如申請專利範圍第1項或第2項所述的樹脂組成物,其進而包含(c)水,且所述樹脂組成物的pH為4~12。
- 如申請專利範圍第4項所述的樹脂組成物,其中所述(a)含有聚醯亞胺的樹脂中所含的通式(1)表示的結構的總數中,R1包含20莫耳%以上的具有芳香族骨架的結構。
- 如申請專利範圍第1項或第2項所述的樹脂組成物,其 中相對於所述(a)含有聚醯亞胺的樹脂的所述酸性官能基100莫耳%,所述(b)鹼性化合物的含量為20莫耳%~450莫耳%。
- 如申請專利範圍第1項或第2項所述的樹脂組成物,其中所述(b)鹼性化合物包含選自鹼金屬中的至少一種元素。
- 如申請專利範圍第3項所述的樹脂組成物,其中所述(c)水佔樹脂組成物中所含的溶媒中的80質量%以上。
- 如申請專利範圍第1項或第2項所述的樹脂組成物,其進而含有(d)填料。
- 如申請專利範圍第14項所述的樹脂組成物,其中所述(d)填料包含碳、錳、鋁、鋇、鈷、鎳、鐵、矽、鈦、錫、及鍺中的至少一種原子。
- 如申請專利範圍第14項所述的樹脂組成物,其中所述(d)填料包含矽、氧化矽、鈦酸鋰、碳化矽、該些中的兩個以上的混合體、該些中的一個或兩個以上的混合體與碳的混合體、及該些中的一個或兩個以上的混合體的表面經碳塗佈而成者中的至少一種。
- 一種積層體,其於基材的至少單面具有由如申請專利範圍第1項或第2項所述的樹脂組成物製膜而成的層。
- 一種積層體的製造方法,其包括:將如申請專利範圍第1項或第2項所述的樹脂組成物塗佈於基材的單面或兩面而形成塗佈膜的步驟;以及將所述塗佈膜乾燥的步驟。
- 一種電極,其包含如申請專利範圍第17項所述的積層體。
- 一種二次電池,其包含如申請專利範圍第19項所述的電極。
- 一種電雙層電容器,其包含如申請專利範圍第19項所述的電極。
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