TW201544503A - 二酸酐與聚醯亞胺 - Google Patents
二酸酐與聚醯亞胺 Download PDFInfo
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- 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
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- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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- 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
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Abstract
本發明提供之二酸酐,其結構為:□,其中Ar係含芴基之基團。上述二酸酐可與二胺聚合形成聚醯亞胺,其重複單元為□,其中Ar係含芴基之基團,且n係介於1至5之間的正整數。上述聚醯亞胺可兼具良好的熱穩定性與熱加工性並適用於多種產業。
Description
本發明係關於聚醯亞胺,更特別關於其二酸酐單體。
一般的聚醯亞胺(polyimide,PI)具有優異的耐熱性、耐化學藥品、良好的機械強度、和電氣絕緣性等性能。PI為高性能高分子材料,已廣泛應用於航空與微機電子等高科技領域。PI通常不溶常見溶劑,因為其芳香環和亞胺基等非極性基團的存在,導致PI分子鏈之間的作用力較強,使PI分子鏈堆積較緊密而難以加工,限制其於某些領域的應用。因此而發展熱可塑性聚醯亞胺(thermoplastic polyimide,TPI)。為了使PI可溶或可熔加工,其單體結構決定PI的性能。TPI常導入柔軟的基團,但後續PI加工常需進行於高溫下,可能導致其結構和熱性能發生變化,從而降低高分子耐熱性並影響其使用性。
綜上所述,目前亟需新的PI單體以同時達到熱可塑性與耐熱性的產品需求。
本發明一實施例提供之二酸酐,其結構為:
,其中Ar係含芴基之基團。
本發明一實施例提供之聚醯亞胺,其重複單元為:,其中Ar係含芴基之基團,且n係介於1至5之間的正整數。
本發明一實施例提供之二酸酐,其結構為式1。
在式1中,Ar係含芴基之基團。舉例來說,Ar之結構可為式2、式3、式4、或其他含芴基之基團。
上述二酸酐可用以與二胺反應形成PI,但不限於
此。舉例來說,二酸酐亦可與二醇反應形成聚酯。若是與二胺反應形成PI,二胺可具有軟性基團(如苯醚基),其結構可為式5。
在式5中,n為介於1至5之間的正整數。在本發明一實施例中,n為1或2。若n的數目過小(比如0),則可能降低PI之分子鏈的可撓性,並降低PI產物的可加工性。若n的數目過大,則可能會降低PI之耐熱性質。
上述二酸酐與二胺之反應如式6所示。在式6中,m為重複數目。在本發明一實施例中,反應中二酸酐與二胺於溶劑中的起始固含量介於15wt%至30wt%之間。若固含量過低,則降低分子碰撞頻率,反應不易進行,聚合度過低。若固含量過高,則溶液黏度過高,不易均勻攪拌。形成PI的反應主要分為兩段,前段開環反應溫度介於0~25℃(室溫)之間,而後段閉環反應溫度介於180~210℃之間。式6之產物即PI,其重均分子量為20000~80000。若PI之重均分子量過高,則對於溶劑溶解度下降,不利用後段成膜製程的應用。若PI之重均分子量過過低,則不易成膜,膜特性質不佳。
在本發明一實施例中,可先將PI熔融製備成厚膜後,再進行MD及TD方向的延伸以得薄膜。藉由調控延伸溫度/倍率/速率,及熱定型溫度/時間的調控,薄膜耐熱性310℃,且熱膨脹係數(CTE,ppm/℃)於MD/TD兩種方向的比值20/10。由此可知,上述PI兼具耐熱性(高熱分解溫度與高玻璃轉換溫度)與良好的熱加工性質。
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
在下述實施例中,PI之重均分子量量測採用凝膠滲透層析儀(Gel Permeation Chromatography)。PI之分子量分佈分析採用折射率偵測器(RI Detector,儀器型號Jasco PU2089),其溶劑系統為二氯甲烷,且標準品為聚苯乙烯(購自力行科技有限公司之Viscotek PolyCAL標準品)。
實施例1(苯基芴單體合成)
將1,2,4-偏苯三酸酐醯氯(120毫莫耳)溶解在60毫升無水THF中。將雙酚芴(60毫莫耳)和吡啶(14.5毫升)溶解在100毫升無水THF中,隨後慢慢滴加至氮氣下的1,2,4-偏苯三酸酐醯氯溶液裡,並於40℃下反應12小時。接著過濾反應結果以去除鹽類,再濃縮濾液以得固體。以正己烷洗滌固體,並用醋酸酐再結晶二次後,可得白色固體產物(產率75%),其氫譜如下:1H NMR(CDCl3,400MHz,ppm):8.77(s,2H),8.69(d,2H),8.14(d,2H),7.82(d,2H),7.43(m,4H)。上述反應如式7所示。
實施例2(萘基芴單體合成)
合成化合物I:將芴(0.54莫耳)、2-萘酚(1.2莫耳)、3-硫醇丙酸(0.0377莫耳)、和300毫升甲苯加入1升反應瓶後,再將10克硫酸慢慢滴入反應瓶中,之後加熱至80℃並於80℃反應10小時。接著將反應結果加入100克的甲苯和30克的水,再以10%氫氧化鈉水溶液將pH調節至7左右,過濾後取濾餅。水洗5次濾餅後,乾燥濾餅後再以石油醚再結晶二次,即可得白色固體化合物I(產率78%)。白色固體化合物I之氫譜如下:1H NMR(CDCl3,400MHz,ppm):7.94(d,2H),7.62(m,8H),7.37(m,6H),7.10(m,4H)。上述反應如式8所示。
接著以類似實施例1之反應步驟,取化合物I與1,2,4-偏苯三酸酐醯氯反應以得白色固體(產率82%),其氫譜如下:1H NMR(CDCl3,400MHz,ppm):8.82(s,2H),8.69(m,4H),7.96(d,2H),7.65(m,8H),7.40(m,6H),7.15(m,4H)。上述反應如式9所示。
實施例3(螺環基芴單體合成)
合成化合物II:混合9-芴酮(60毫莫耳)、1,3-苯二醇(240毫莫耳)、和氯化鋅(27.01毫莫耳),加熱至140℃後於140℃下維持於3小時,在熔融狀態下慢慢加入150毫升濃鹽酸後迴流2小時。隨後倒入1升冰水中再沉澱。過濾後取濾餅,以正己烷沖洗濾餅後以石油醚再結晶二次,即可得白色固體化合物II(產率70%),其氫譜如下:1H NMR(CDCl3,400MHz,ppm):7.90(d,2H),7.42(dd,2H),7.23(dd,2H),7.08(d,2H),6.68(d,2H),6.31(d,2H),6.13(d,2H)。上述反應如式10所示。
接著以類似實施例1之反應步驟,取化合物II與1,2,4-偏苯三酸酐醯氯反應以得白色固體(產率82%),其氫譜如下:1H NMR(CDCl3,400MHz,ppm):8.80(s,2H),8.65(m,4H),7.90(d,2H),7.45(dd,2H),7.26(dd,2H),7.18(d,2H),6.67(d,2H),6.33(d,2H),6.15(d,2H)。上述反應如式11所示。
實施例4(TPI高分子合成)
將實施例1合成之苯芴單體(10毫莫耳)溶解於NMP中,隨後加入4,4'-二胺基二苯醚(10毫莫耳),並調整上述液體之固含量為30%。接著在氮氣及室溫下反應24小時後,再加入適量甲苯並加熱至200℃並於200℃下反應12小時。上述反應搭配Dean-Stark trap裝置,以於反應中逐漸移除甲苯和水。反應後降至室溫,再將反應結果倒入甲醇以沉澱析出固體。過濾後乾燥濾餅,再將濾餅溶於少量NMP中,再加入甲醇以再沉澱固體。過濾後保留濾餅。乾燥後即可得淡黃色固體(產率95%),其氫譜如下:1H NMR(CDCl3,400MHz,ppm):8.72(s,2H),8.60(d,2H),8.08(d,2H),7.81(d,2H),7.53-7.31(m,14H),7.25-7.10(m,8H)。上述反應如式12所示,m為重複數目。上述產物即PI,其重均分子量為73260,分子量分佈為88172~59603。上述PI之熱分解溫度為471℃,屬於耐熱材料。上述PI之Tg為296℃。在雙軸延伸PI後(延伸倍率:3倍,延伸溫度:300℃),其Tg為308℃。由上述可知,上述PI兼具耐熱性與良好的熱加工性質。
實施例5
與實施例4類似,差別在於將實施例1之苯芴單體置換為苯萘單體。至於其他反應物與製程參數均與實施例4類似。實施例5之反應如式13所示,m為重複數目。上述產物即PI,其重均分子量為64110,分子量分佈為78311~51023。上述PI之熱分解溫度為485℃,屬於耐熱材料。上述PI之Tg為302℃。在雙軸延伸PI後(延伸倍率:3倍,延伸溫度:305℃),其Tg為315℃。由上述可知,上述PI兼具耐熱性與良好的熱加工性質。
實施例6
與實施例4類似,差別在於將實施例1之苯芴單體置換為苯萘單體。至於其他反應物與製程參數均與實施例4類似。實施例6之反應如式14所示,m為重複數目。上述產物即PI,其重均分子量為43840,分子量分佈為55631~32008。上述PI之熱分解溫度為481℃,屬於耐熱材料。上述PI之Tg為311℃。在雙軸延伸PI後(延伸倍率:3倍,延伸溫度:315℃),其Tg為319℃。由上述可知,上述PI兼具耐熱性與良好的熱加工性質。
雖然本發明已以數個實施例揭露如上,然其並非用以限定本發明,任何本技術領域中具有通常知識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 (10)
- 一種二酸酐,其結構為:
- 如申請專利範圍第1項所述之二酸酐,其中Ar之結構為:
- 如申請專利範圍第1項所述之二酸酐,其中Ar之結構為:
- 如申請專利範圍第1項所述之二酸酐,其中Ar之結構為:
- 一種聚醯亞胺,其重複單元為: ,其中Ar係含芴基之基團,且n係介於1至5之間的正整數。
- 如申請專利範圍第5項所述之聚醯亞胺,其中Ar之結構為:
- 如申請專利範圍第5項所述之聚醯亞胺,其中Ar之結構為:
- 如申請專利範圍第5項所述之聚醯亞胺,其中Ar之結構為:
- 如申請專利範圍第5項所述之聚醯亞胺,其中n為1或2。
- 如申請專利範圍第5項所述之聚醯亞胺,其重均分子量介於20000~80000之間。
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2015
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- 2015-05-28 CN CN201510281738.4A patent/CN105218813B/zh active Active
- 2015-05-28 TW TW104117124A patent/TWI548634B/zh active
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TWI548634B (zh) | 2016-09-11 |
CN105218813B (zh) | 2017-10-27 |
US20150344626A1 (en) | 2015-12-03 |
CN105218813A (zh) | 2016-01-06 |
US9416229B2 (en) | 2016-08-16 |
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