通过三步反应合成了一种新型具有高度扭曲构型的芳香二胺单体1,2-双(4-(4-氨基-2-三氟甲基苯氧基)苯基)-菲并[9,10-d]咪唑(PIPOTFA),将它与四种商业化二酐4,4'-六氟异丙基邻苯二甲酸酐(6FDA)、3,3',4,4'-二苯醚四甲酸二酐(ODPA)、3,3',4,4'-联苯四甲酸二酐(BPDA)和3,3',4,4'-二苯甲酮四甲酸二酐(BTDA)通过高温一步法聚合制得了四种聚酰亚胺均聚物。这些聚酰亚胺在N-甲基吡咯烷酮(NMP)、N,N-二甲基乙酰胺(DMAc)和N,N-二甲基甲酰胺(DMF)等非质子极性溶剂中均具有良好的溶解性。热分析测试结果表明,这些聚酰亚胺具有优异的热稳定性,其玻璃化转变温度在265~290℃之间,氮气气氛下5%和10%热失重温度分别为517~561℃和547~587℃,700℃时的残炭率为60%~70%。这些聚酰亚胺薄膜呈淡黄色,在450nm处的透过率为11%~68%,截止波长为375~383nm。
A highly twisted aromatic diamine monomer,1,2-bis(4-(4-amino)-2-trifluoromethylphenoxy) phenyl)-phenanthro[9,10-d] imidazole (PIPOTFA),was synthesized through three-step reactions.Novel polyimide(PI) was synthesized by condensation polymerization of the PIPOTFA with four commercial dianhydride monomers,4,4'-(hexafluoroisopropylidene)diphthalic anhydride (6FDA),4,4'-oxydiphthalic anhydride (ODPA),3,3',4,4'-biphenyltetracarboxylic dianhydride (BPDA) and 3,3',4,4'-benzophenonetetracarboxylic dianhydride (BTDA) through one-step high-temperature condensation polymerization method.The resulting PI was well soluble in common aprotic polar solvent such as N-methylpyrrolidone (NMP),N,N-dimethylacetamide (DMAc),and N,N-dimethylformamide (DMF).Thermal analysis test results revealed that the PI had excellent thermal stability.The glass transition temperatures (Tg) of the PI were around 265~290℃,and the 5% and 10% thermal weight loss temperatures in nitrogen were in the range 517~561℃ and 547~587℃,respectively.Moreover,the char yields were as high as 60%~70% at 700℃ in nitrogen.These PI films appeared pale yellowish color and the transmittance values at 450nm were in the range 11%~68%,while the cut-off wavelength (λ0) values were around 375~383nm.
[1] Min K I,Lee T H,Park C P,et al.Monolithic and flexible polyimide film microreactors for organic microchemical applications fabricated by laser ablation[J].Angewandte Chemie-International Edition,2010,49(39):7063-7067.
[2] SekitaniI T,Zschieschang U,Klauk H,et al.Flexible organic transistors and circuits with extreme bending stability[J].Nature Materials,2010,9(12):1015-1022.
[3] Liaw D J,Wang K L,Huang Y C,et al.Advanced polyimide materials:syntheses,physical properties and applications[J].Progress in Polymer Science,2012,37(7):907-974.
[4] Lim H,Cho W J,Ha C S,et al.Flexible organic electroluminescent devices based on fluorine-containing colorless polyimide substrates[J].Advanced Materials,2002,14(18):1275-1279.
[5] Liaw D J,Liaw B Y,Yu C W.Synthesis and characterization of new organosoluble polyimides based on flexible diamine[J].Polymer,2001,42(12):5175-5179.
[6] Fang X Z,Wang Z,Yang Z H,et al.Novel polyimides derived from 2,3,3',4'-benzophenonetetracarboxylic dianhydride[J].Polymer,2003,44(9):2641-2646.
[7] Lin S H,Li F,Cheng S Z D,et al.Organo-soluble polyimides:synthesis and polymerization of 2,2'-bis(trifluoromethyl)-4,4',5,5'-biphenyltetracarboxylic dianhydride[J].Macromolecules,1998,31(7):2080-2086.
[8] Kim S D,Lee S,Heo J,et al.Soluble polyimides with trifluoromethyl pendent groups[J].Polymer,2013,54(21):5648-5654.
[9] Yang C P,Su Y Y,Wen S J,et al.Highly optically transparent/low color polyimide films prepared from hydroquinone- or resorcinol-based bis(ether anhydride) and trifluoromethyl-containing bis(ether amine)s[J].Polymer,2006,47(20):7021-7033.
[10] Zhuang Y,Seong J G,Do Y S,et al.Effect of isomerism on molecular packing and gas transport properties of poly(benzoxazole-co-imide)s[J].Macromolecules,2014,47(22):7947.
[11] Lu Y H,Hu Z Z,Wang Y F,et al.Synthesis and properties of organosoluble and transparent fluorinated aromatic polyimides[J].Advanced Materials Research,2011,391-392:888-893.
[12] Wang C Y,Li G,Jiang J M.Synthesis and properties of fluorinated poly(ether ketone imide)s based on a new unsymmetrical and concoplanar diamine:3,5-dimethyl-4-(4-amino-2-trifluoromethylphenoxy)-4'-aminobenzophenone[J].Polymer,2009,50(7):1709-1716.
[13] Liaw D J,Chang F C,Leung M K,et al.High thermal stability and rigid rod of novel organosoluble polyimides and polyamides based on bulky and noncoplanar naphthalene-biphenyldiamine[J].Macromolecules,2005,38(9):4024-4029.
[14] Guo X,Fang J,Kazuhiro T,et al.Synthesis and properties of novel sulfonated polyimides from 2,2'-bis(4-aminophenoxy)biphenyl-5,5'-disulfonic acid[J].Journal of Polymer Science Part A Polymer Chemistry,2004,42(6):1432-1440.
[15] Yang C P,Su Y Y.Properties of organosoluble aromatic polyimides from 3'-trifluoromethyl-3,4'-oxydianiline[J].Polymer,2003,44(20):6311-6322.
[16] Mushtaq N,Chen G,Sidra L R,et al.Organosoluble and high Tg polyimides from asymmetric diamines containing N-amino and N-aminophenyl naphthalimide moieties[J].Rsc Advances,2016,6(30):25302-25310.
[17] Zeng K,Zhou S,Fan H,et al.Synthesis and characterization of highly organosoluble polyimides based on a new asymmetric dianhydride[J].Designed Monomers & Polymers,2012,15(1):53-62.
[18] Wen C C,Ju Y H,Yeh H K,et al.Novel organosoluble aromatic polyimides bearing pendant methoxy-substituted triphenylamine moieties:synthesis,electrochromic,and gas separation properties[J].Journal of Polymer Science Part A Polymer Chemistry,2008,46(24):7937-7949.
[19] Wu Q,Ma X,Zheng F,et al.Synthesis of highly transparent and heat-resistant polyimides containing bulky pendant moieties[J].Polymer International,2019,68(6):1186-1193.
[20] Wang C,Zhao X,Li G,et al.High solubility and optical transparency of novel polyimides containing 3,3',5,5'-tetramethyl pendant groups and 4-tert-butyltoluene moiety[J].Polymer Degradation and Stability,2009,94(9):1526-1532.
[21] Ghaemy M,Berenjestanaki F R,Bazzar M.Organosoluble,thermally stable and low dielectric constant fluorinated polyimides containing 2,4,5-triphenylimidazole moiety in the main chains[J].Designed Monomers & Polymers,2014,17(2):101-110.
[22] Ghaemy M,Hassanzadeh M,Taghavi M,et al.Synthesis and characterization of trifluoromethylated poly(ether-imidazole-imide)s based on unsymmetrical diamine bearing carbazole and imidazole chromophores in ionic liquids:study of electrochemical properties by using nanocomposite electrode[J].Journal of Fluorine Chemistry,2012,142:29-40.
[23] Lindner.Imidazolium-based polymers via the poly-radziszewski reaction[J].Macromolecules,2016,49(6):2046-2053.
[24] Debus S H.Ueber die einwirkung des ammoniaks auf glyoxal[J].European Journal of Organic Chemistry,2010,107(2):199-208.
[25] Kumar D,Gupta A D.Aromatic cyclolinear phosphazene polyimides based on a novel bis-spiro-substituted cyclotriphosphazene diamine[J].Macromolecules,1995,28(18):6323-6329.
基金资助
国家“973”计划项目(2014CB643600);National Research Foundation of Korea(韩国研究财团)funded by the Ministry of Science and ICT,Korea(韩国,科学技术情报通信部)(NRF-2017R1A2B3012961;Brain Korea 21Four Program)