TWI492967B - 聚亞醯胺 - Google Patents

聚亞醯胺 Download PDF

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TWI492967B
TWI492967B TW100149775A TW100149775A TWI492967B TW I492967 B TWI492967 B TW I492967B TW 100149775 A TW100149775 A TW 100149775A TW 100149775 A TW100149775 A TW 100149775A TW I492967 B TWI492967 B TW I492967B
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formula
moles
bisamine
added
solution
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TW201326256A (zh
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Hsueh Yi Liao
Chyi Ming Leu
Tzong Ming Lee
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Ind Tech Res Inst
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1003—Preparatory processes
    • C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1042—Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1046—Polyimides containing oxygen in the form of ether bonds in the main chain
    • C08G73/105—Polyimides containing oxygen in the form of ether bonds in the main chain with oxygen only in the diamino moiety
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
    • C08G73/1071—Wholly aromatic polyimides containing oxygen in the form of ether bonds in the main chain

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

Description

聚亞醯胺
本發明係關於聚亞醯胺，更特別關於形成聚亞醯胺內特定比例的單體結構。
聚亞醯胺屬於耐熱材料，具有極佳的熱性質、機械性質、及電性質，並可應用於多種領域中。為了使聚亞醯胺具有較佳的耐熱性，較佳採用芳香性單體。由於大部份的芳香性的聚亞醯胺之溶解度不佳，或是難以維持穩定的黏度而存放不易。
綜上所述，目前極需新的聚亞醯胺組成以達成高溶解度與存放性的要求。
本發明一實施例提供一種聚亞醯胺，係由a莫耳份之第一雙胺、b莫耳份之第二雙胺、與100莫耳份之第一雙酸酐共聚而成，其中第一雙胺之結構如下：；第二雙胺之結構如下：；第一雙酸酐之結構如下：；a+b=100，50a80，且20b50。
本發明一實施例提供一種聚亞醯胺，係由a莫耳份之第一雙胺、b莫耳份之第二雙胺、c莫耳份之第一雙酸酐、及d莫耳份之第二雙酸酐共聚而成，其中第一雙胺之結構如下：；第二雙胺之結構如下：；第一雙酸酐之結構如下：；第二雙酸酐之結構如下：；a+b=c+d=100，50a80，20b50，60c<100，且0<d40。
本發明一實施例提供一種聚亞醯胺，係由a莫耳份之第一雙胺、b莫耳份之第二雙胺、與100莫耳份之第一雙酸酐共聚而成。a+b=100，50a80，且20b50。若第一雙胺之用量過低，則合成過程中因為溶解度關係造成產生之聚亞醯胺聚合物析出，無法溶解。第一雙胺之結構如式1所示，第二雙胺之結構如式2所示，而第一雙酸酐之結構如式3所示。
上述雙胺與雙酸酐共聚後形成式4所示之聚亞醯胺，其分子量與相對黏度相關，當相對黏度越高，其分子量亦越高。舉例來說，聚亞醯胺之相對黏度約介於1000~5000cps(25℃)之間。製備後之聚亞醯胺可溶於溶劑如甲苯、間甲酚、N-甲基咯烷酮、或上述之組合。聚亞醯胺溶液在塗佈於基材上後，可以薄膜烘烤製程約50℃~200℃，150~200分鐘來去除溶劑，即形成聚亞醯胺薄膜。
式4所示之聚亞醯胺，其中對應重複數目b之重複單元與對應重複數目a之重複單元組成無規(random)共聚物或嵌段(block)共聚物。
本發明一實施例提供之聚亞醯胺，係由a莫耳份之第一雙胺、b莫耳份之第二雙胺、c莫耳份之第一雙酸酐、及d莫耳份之第二雙酸酐共聚而成。a+b=c+d=100，50a80，20b50，60c<100，且0<d40。第一雙胺之結構如式1所示，第二雙胺之結構如式2所示，第一雙酸酐之結構如式3所示，而第二雙酸酐之結構如式5所示。
上述雙胺與雙酸酐共聚後形成式6所示之聚亞醯胺，其中a1+a2=a，b1+b2=b，a1+b1=c，且a2+b2=d。式6所示之聚亞醯胺，其中對應重複數目a1、a2、b1與b2之重複單元組成無規(random)共聚物或嵌段(block)共聚物。
上述聚亞醯胺之分子量與相對黏度相關，當相對黏度越高，其分子量亦越高。舉例來說，聚亞醯胺之相對黏度介於2000~30000cps(25℃)之間。製備後之聚亞醯胺可溶於溶劑如甲苯、間甲酚、N-甲基咯烷酮、或上述之組合。
在一實施例中，聚亞醯胺在室溫約20~30℃(例如約25℃)之下，於約1~180天之中，相對黏度的變化量約小於10%或小於5%，在一些實施例中，相對黏度的變化量甚至約小於1%。
為了讓本發明之上述和其他目的、特徵、和優點能更明顯易懂，下文特舉數實施例配合所附圖示，作詳細說明如下：
【實施例】
實施例1
取50莫耳份式2所示的雙胺(37.47g)及50莫耳份式1所示的雙胺(63.53g)溶於913.65ml之間甲酚中。接著將60莫耳份式3所示之雙酸酐(88.64g)與40莫耳份式5所示之雙酸酐(40.0g)加至上述間甲酚溶液中，再加入0.23g之異喹啉作為催化劑。先在室溫下攪拌5分鐘後，升溫至220℃反應4小時。上述反應在降至室溫後加入127.57g之甲苯及255.15g的間甲酚作為稀釋劑。25℃下具有15%固含量之上述溶液的相對黏度為9125cps。將上述溶液置於室溫下(約20℃至30℃之間)觀察其黏度變化，其黏度與放置時間如第1表所示。由第1表可知，本發明之可溶聚亞醯胺的溶液在長期放置後的相對黏度不會大幅改變。
上述可溶聚亞醯胺之Tg為310℃，Td為498.53℃，可以薄膜烘烤製程50℃逐漸升溫至200℃共180分鐘來去除溶劑，即形成聚亞醯胺薄膜，測得破壞電壓為5.2kV。
實施例2
取40莫耳份式2所示的雙胺(35.99g)及60莫耳份式1所示的雙胺(61.01g)溶於913.65ml之間甲酚中。接著將60莫耳份式3所示之雙酸酐(88.64g)與40莫耳份式5所示之雙酸酐(40.0g)加至上述間甲酚溶液中，再加入0.23g之異喹啉作為催化劑。先在室溫下攪拌5分鐘後，升溫至220℃反應4小時。上述反應在降至室溫後加入91.47g之甲苯及284.58g的間甲酚作為稀釋劑。25℃下具有15%固含量之上述溶液的相對黏度為15600cps。上述可溶聚亞醯胺之Tg為300℃，Td為498.53℃，可以薄膜烘烤製程50℃逐漸升溫至200℃共180分鐘來去除溶劑，即形成聚亞醯胺薄膜，測得破壞電壓為5.2kV。
實施例3
取20莫耳份式2所示的雙胺(17.99g)及80莫耳份式1所示的雙胺(81.35g)溶於563.77ml之N-甲基咯烷酮中。接著將80莫耳份式3所示之雙酸酐(118.18g)與20莫耳份式5所示之雙酸酐(20.0g)加至上述N-甲基咯烷酮溶液中，再加入4.75g之異喹啉作為催化劑。先在室溫下攪拌5分鐘後，升溫至220℃反應4小時。上述反應在降至室溫後加入395.87g的N-甲基咯烷酮作為稀釋劑，攪拌後得固含量為30%之可溶聚亞醯胺溶液。25℃下具有15%固含量之上述溶液的相對黏度為2760cps。上述可溶聚亞醯胺之Tg為320℃，且Td為506.08℃。
實施例4
取20莫耳份式2所示的雙胺(6.09g)及80莫耳份式1所示的雙胺(27.53g)溶於192.12ml之N-甲基咯烷酮中。接著將100莫耳份式3所示之雙酸酐(50.0g)加至上述N-甲基咯烷酮溶液中，再加入4.75g之異喹啉作為催化劑。先在室溫下攪拌5分鐘後，升溫至220℃反應4小時。上述反應在降至室溫後加入134.5g的N-甲基咯烷酮作為稀釋劑，攪拌後得固含量為30%之可溶聚亞醯胺溶液。25℃下具有15%固含量之上述溶液的相對黏度為1500cps，且上述溶液具有可流動性，有利於成膜。將上述溶液置於室溫下(約20℃至30℃之間)觀察其黏度變化，其黏度與放置時間如第2表所示。由第2表可知，本發明之可溶聚亞醯胺的溶液在長期放置後的相對黏度不會大幅改變。
比較例1
取30莫耳份式2所示的雙胺(5.4g)及70莫耳份式1所示的雙胺(12.24g)溶於105.50ml之N-甲基咯烷酮中。接著將50莫耳份式3所示之雙酸酐(14.77g)與50莫耳份式5所示之雙酸酐(10.0g)加至上述N-甲基咯烷酮溶液中，再加入0.44g之異喹啉作為催化劑。先在室溫下攪拌5分鐘後，升溫至220℃反應4小時。上述反應在降至室溫後整鍋為膠狀，即使加入大量溶劑仍不溶。
比較例2
取60莫耳份式2所示的雙胺(14.05g)及40莫耳份式1所示的雙胺(34.42g)溶於196.98ml之N-甲基咯烷酮中。接著將100莫耳份式3所示之雙酸酐(50g)加至上述N-甲基咯烷酮溶液中，再加入1.69g之異喹啉作為催化劑。先在室溫下攪拌5分鐘後，升溫至220℃反應4小時。上述反應在降至室溫後整鍋為膠狀，即使加入大量溶劑仍不溶。
比較例3
取60莫耳份式2所示的雙胺(14.05g)及40莫耳份式1所示的雙胺(10.09g)溶於132.3ml之N-甲基咯烷酮中。接著將60莫耳份式3所示之雙酸酐(22.16g)與40莫耳份式5所示之雙酸酐(10.0g)加至上述N-甲基咯烷酮溶液中，再加入0.57g之異喹啉作為催化劑。先在室溫下攪拌5分鐘後，升溫至220℃反應4小時。上述反應在降至室溫後溶液中含有部份膠狀物，無法順利塗佈於基板上。
雖然本發明已以數個較佳實施例揭露如上，然其並非用以限定本發明，任何熟習此技藝者，在不脫離本發明之精神和範圍內，當可作任意之更動與潤飾，因此本發明之保護範圍當視後附之申請專利範圍所界定者為準。

Claims (3)

  1. 一種聚亞醯胺，係由a莫耳份之第一雙胺、b莫耳份之第二雙胺、c莫耳份之第一雙酸酐、及d莫耳份之第二雙酸酐共聚而成，其中該第一雙胺之結構如下： 該第二雙胺之結構如下： 該第一雙酸酐之結構如下： 該第二雙酸酐之結構如下： a+b=c+d=100，50a80，20b50，60c<100，且0<d40。
  2. 如申請專利範圍第1項所述之聚亞醯胺，其相對黏度介於2000~30000cps。
  3. 如申請專利範圍第1項所述之聚亞醯胺，在20~30℃之間置放約1~180天後的相對黏度變化量小於10%。
TW100149775A 2011-12-30 2011-12-30 聚亞醯胺 TWI492967B (zh)

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