新型含二氮杂萘酮联苯结构聚苯并咪唑的合成
|
摘要
聚苯并咪唑以其优良的耐热性能和机械性能在高性能高分子材料领域占有重要的地位,具有广泛的应用前景。然而,已商品化聚苯并咪唑的溶解性能和熔融较差,加工困难,限制了其在一些领域的应用。本文将扭曲、非共平面的二氮杂萘酮联苯结构引入到聚苯并咪唑的主链中,合成了一系列含二氮杂萘酮联苯结构的新型聚苯并咪唑高性能聚合物,优化合成条件;对其结构和性能进行研究,以揭示该类聚合物的结构与性能关系。
本文首先从分子设计出发,以自制的4-[4-(4-羧基苯氧基)苯基]-2-(4-羧基苯基)二氮杂萘-1-酮(DHPZ-DA),为二酸单体,与3,3'-二氨基联苯胺(DAB)进行缩聚反应,制备了含二氮杂萘酮联苯结构的聚苯并咪唑均聚物,系统研究了影响聚合反应的各种因素,对聚合反应工艺进行了优化,聚合物的特性粘度达到1.63 dL/g;并以DHPZ-DA和间苯二酸(IPA)为二酸单体,采用不同摩尔配比,与DAB进行共缩聚,制备了一系列具有不同二氮杂萘酮联苯结构含量的聚苯并咪唑共聚物。聚合体系以多聚磷(PPA)为溶剂,采用高温溶液缩聚体系。利用红外光谱(FT-IR)、核磁共振氢谱(~1H NMR)、广角X射线衍射(WAXD)、扫描量热分析(DSC)和热失重分析仪(TGA)等测试手段对所合成的聚合物进行结构表征和性能测试,结果表明,所合成的聚合物结构与设计相一致;大部分聚合物具有无定形结构,所合成的均聚物和大部分共聚物可溶解于N,N-二甲基乙酰胺等极性非质子溶剂中;所合成含二氮杂萘酮联苯结构的聚苯并咪唑具有优异的耐热性能,含二氮杂萘酮联苯结构聚苯并咪唑的玻璃化转变温度(T_g)由398～408℃,5%热失重均在516℃以上。由此可见,PPBI既耐高温又可溶解,综合性能优于传统聚苯并咪唑。
利用二氮杂萘酮联苯结构可以赋予聚合物良好溶解性的特点,将DHPZ-DA分别与自制的3,3',4,4'-四氨基二苯醚(TADE)、1,4-2(3,4-氨基苯氧基)苯(BAPP)和4,4'-2(3,4-氨基苯氧基)联苯(BAPBP)直接共聚,经高温溶液缩聚反应成功合成了带醚键的可溶性的聚苯并咪唑。通过对聚合物进行结构表征和性能测试,结果表明,所合成的聚合物结构与设计相一致;聚合物均为无定形结构,所合成的聚合物均可溶于N-甲基吡咯烷酮等有机非质子溶剂中;此外,聚合物T_(5%)均高于508℃,在450℃之前无明显的热失重,说明这些聚合物的热稳定性很好。
Polybenzimidazole has been noted as a kind of important polymeric material,which presents a combination of outstanding properties,such as high thermal stability,good chemical resistance and excellent mechanical properties.However,the commercial polybenzimidazoles have poor solubility in most organic solvents at room temperature,which resulted in difficulty for processing.In this work,our efforts have been focused on synthesis of polybenzimidazoles with good solubility and high thermal properties by introduction of twisted and non-coplanar phthalazinone moieties into polybenzimidazole backbones.
In this thesis,a novel polybenzimidazole containing twist and non-coplanar phthalazinone moieties was synthesized from 3,3'-diaminobenzidine(DAB) and 4-(4-(4-(4-carboxyphenoxy)phenyl)-1-oxophthalazin-2(1H)-yl)benzoic acid(DHPZ-DA). The synthesis process was optimized.After the optimization of the polymerization,the inherent viscosity of this polymer could reach 1.63 dL/g.A series of co-polybenzimidazoles were synthesized by condensation of 3,3'-diaminobenzidine(DAB) with a mixture of DHPZ-DA and isophthalic acid(IPA) in different ratio in polyphosphoric acid(PPA).The polybenzimidazoles were characterized by different instrumental techniques(FT-IR,~1H NMR, WAXD,DSC and TGA).The polymers have good solubility in polar aprotic solvents,such as N-methyl-2-pyrolidinone(NMP),N,N-dimethylacetamide(DMAc),etc.Most of the polybenzimidazoles exhibited amorphous nature as evident by WAXD.The resultant polybenzimidazoles show high thermal stability with the glass transition temperatures of the copolymers from 398℃to 408℃,and the temperatures for 5%weight loss of the copolymers above 516℃.
Soluble polybenzimidazoles containing ether linkages and twisted and non-coplanar phthalazinone moieties in the the main chains were successfully synthesized by condensation of DHPZ-DA with 3,3',4,4'-tetramino diphenyl ether(TADE), 1,4-bis(3,4-nitrophenoxy)phenyl(BAPP) and 4,4'-bis(3,4-aminophenoxy)biphenyl(BAPBP) in PPA,respectively.The polybenzimidazoles were characterized by different instrumental techniques.The polymers have good solubility in polar aprotic solvents,such as N-methyl-2-pyrolidinone(NMP),etc.All polybenzimidazoles exhibited amorphous nature as evident by WAXD.The 5%weight loss temperatures for the polybenzimidazoles were all higher than 508℃.
本文首先从分子设计出发,以自制的4-[4-(4-羧基苯氧基)苯基]-2-(4-羧基苯基)二氮杂萘-1-酮(DHPZ-DA),为二酸单体,与3,3'-二氨基联苯胺(DAB)进行缩聚反应,制备了含二氮杂萘酮联苯结构的聚苯并咪唑均聚物,系统研究了影响聚合反应的各种因素,对聚合反应工艺进行了优化,聚合物的特性粘度达到1.63 dL/g;并以DHPZ-DA和间苯二酸(IPA)为二酸单体,采用不同摩尔配比,与DAB进行共缩聚,制备了一系列具有不同二氮杂萘酮联苯结构含量的聚苯并咪唑共聚物。聚合体系以多聚磷(PPA)为溶剂,采用高温溶液缩聚体系。利用红外光谱(FT-IR)、核磁共振氢谱(~1H NMR)、广角X射线衍射(WAXD)、扫描量热分析(DSC)和热失重分析仪(TGA)等测试手段对所合成的聚合物进行结构表征和性能测试,结果表明,所合成的聚合物结构与设计相一致;大部分聚合物具有无定形结构,所合成的均聚物和大部分共聚物可溶解于N,N-二甲基乙酰胺等极性非质子溶剂中;所合成含二氮杂萘酮联苯结构的聚苯并咪唑具有优异的耐热性能,含二氮杂萘酮联苯结构聚苯并咪唑的玻璃化转变温度(T_g)由398～408℃,5%热失重均在516℃以上。由此可见,PPBI既耐高温又可溶解,综合性能优于传统聚苯并咪唑。
利用二氮杂萘酮联苯结构可以赋予聚合物良好溶解性的特点,将DHPZ-DA分别与自制的3,3',4,4'-四氨基二苯醚(TADE)、1,4-2(3,4-氨基苯氧基)苯(BAPP)和4,4'-2(3,4-氨基苯氧基)联苯(BAPBP)直接共聚,经高温溶液缩聚反应成功合成了带醚键的可溶性的聚苯并咪唑。通过对聚合物进行结构表征和性能测试,结果表明,所合成的聚合物结构与设计相一致;聚合物均为无定形结构,所合成的聚合物均可溶于N-甲基吡咯烷酮等有机非质子溶剂中;此外,聚合物T_(5%)均高于508℃,在450℃之前无明显的热失重,说明这些聚合物的热稳定性很好。
Polybenzimidazole has been noted as a kind of important polymeric material,which presents a combination of outstanding properties,such as high thermal stability,good chemical resistance and excellent mechanical properties.However,the commercial polybenzimidazoles have poor solubility in most organic solvents at room temperature,which resulted in difficulty for processing.In this work,our efforts have been focused on synthesis of polybenzimidazoles with good solubility and high thermal properties by introduction of twisted and non-coplanar phthalazinone moieties into polybenzimidazole backbones.
In this thesis,a novel polybenzimidazole containing twist and non-coplanar phthalazinone moieties was synthesized from 3,3'-diaminobenzidine(DAB) and 4-(4-(4-(4-carboxyphenoxy)phenyl)-1-oxophthalazin-2(1H)-yl)benzoic acid(DHPZ-DA). The synthesis process was optimized.After the optimization of the polymerization,the inherent viscosity of this polymer could reach 1.63 dL/g.A series of co-polybenzimidazoles were synthesized by condensation of 3,3'-diaminobenzidine(DAB) with a mixture of DHPZ-DA and isophthalic acid(IPA) in different ratio in polyphosphoric acid(PPA).The polybenzimidazoles were characterized by different instrumental techniques(FT-IR,~1H NMR, WAXD,DSC and TGA).The polymers have good solubility in polar aprotic solvents,such as N-methyl-2-pyrolidinone(NMP),N,N-dimethylacetamide(DMAc),etc.Most of the polybenzimidazoles exhibited amorphous nature as evident by WAXD.The resultant polybenzimidazoles show high thermal stability with the glass transition temperatures of the copolymers from 398℃to 408℃,and the temperatures for 5%weight loss of the copolymers above 516℃.
Soluble polybenzimidazoles containing ether linkages and twisted and non-coplanar phthalazinone moieties in the the main chains were successfully synthesized by condensation of DHPZ-DA with 3,3',4,4'-tetramino diphenyl ether(TADE), 1,4-bis(3,4-nitrophenoxy)phenyl(BAPP) and 4,4'-bis(3,4-aminophenoxy)biphenyl(BAPBP) in PPA,respectively.The polybenzimidazoles were characterized by different instrumental techniques.The polymers have good solubility in polar aprotic solvents,such as N-methyl-2-pyrolidinone(NMP),etc.All polybenzimidazoles exhibited amorphous nature as evident by WAXD.The 5%weight loss temperatures for the polybenzimidazoles were all higher than 508℃.
引文
[1]Hofmann k Imidazole and its Derivatives[M].New York:Interscience,1953.
[2]Steck E A,Nachold F C,Ewing G W.Absorption spectra of heterocyclic compounds.Ⅲ.Some Benzimidazole Derivatives[J].Jourmal of the American Chemical Society,1948,70(10):3406-3410.
[3]Anthony B C,Edward C C,Thomas C B,et al.Polymerization and spinning of PBI[J].Journal of Polymer Science Part C:Polymer Symposia,1972,19(1):49-64.
[4]刘志刚,傅秦生,焦平坤,等。CFCs替代工质筛选的热力学原则[C].全国高等学校工程热物理第四届学术会议论文集.杭州:浙江大学出版社,1992,73-76.
[5]Cassidy P E.Thermally stable polymers,synthesis and properties[M].New York:Marcel Dekker,1980.
[6]Meisenheimer J and Wieger B.Mitteilung aus dem Ⅱ.Chemischen Institue der Universitat Budapest Uber N-Vinylbenzimidazole[J].Journal fur Praktische chemie,1921,102(1):45-62.
[7]Overberger C G,Pierre T St,Vorchheimer N,et al.The esterolytic catalysis of Poly-4(5)-vinylimidazole and Poly-5(6)-vinylbenzimidazole[J].Jourmal of the American Chemical Society,1963,85(20):3513-3515.
[8]Deborah J.Jones,Jacques Rozi(?)re.Recent advances in the functionalisation of polybenzimidazole and polyetherketone for fuel cell applications[J].Journal of Membrane Science,2001,185(1):41-58.
[9]Price J A,Corm S.Polymerizable compositions comprising 2-vinylbenzimidazole and polymerization products:US,2606175[P].1952,08,05.
[10]Vogel H,Marvel C S.Polybenzimidazoles,new thermally stable polymers[J].Journal of Polymer Science Part A:General Papers,1961,50(154):511-539.
[11]Brinker K C,Robinson I M.Polybenzimidazoles:US,2895948[P].1995,10,28.
[12]Levine H H,Calif L J.Fusible Polybenzimidzaole polymer product and process:US,3533879[P].1970,10,13.
[13]Brinegar W C.Production of semipermeable polubenzimidazole membranes:US,3841492[P].1974,10,15.
[14]Powers E J,Hassinger W P,Heights B,et al.Process for the dyeing of polybenzimidole fibers with anionic dyestuffs:US,3942950[P].1997,03,09.
[15]Tan M,N.J R P.Process for producing high-strength,ultralow dening polybenzimidazole(PBI) filaments:US,4263245[P].1981,04,23.
[16]Stuetz D E,N.J W.Production of activated carbon fibers from acid contacted polybenzimidazole fibrous material:US,4460708.1984,07,17.
[17]Summa G D,MO R.Positive retraction trolley stop for power and free conveyors:US,4898099[P].1990,02,06.
[18]Sansone M J,N.J B H.Process for the production of polybenzimidazole ultrafiltration membranes:US,4693824[P].1987,09,05.
[19]Marikar Y M F,Plains S,Besso M M,et al.Process for preparing electrically conductive shaped articles from polybenzimidazoles:US 4868008[P].1989,09,19.
[20]Wadhwa L,Plainfield N,Bitritto M,et al.Fabrication of high performance polybenzimidazole films:US,4927909[P].1987,09,18.
[21]Sansong M J,Height B,Onorato F J,et al.Acid-modified polybenzimidazole fuel cell elements:US,5599639[P].1995,10,27.
[22]Plummer L.Marvel C S.Polybenzimidazoles Ⅲ[J].Journal of Polymer Science Part A:General Paper 1964,2(6):2559-2569.
[23]Tsur Y,Levine H H,Levy M.Effects of structure on properties of some new aromatic-aliphatic polybenzimidazoles[J].Journal of Polymer Science:Polymer Chemistry Edition,1974,12(7):1515-1529.
[24]Foster R T,Marvel C S.Polybenzimidazoles Ⅳ.Polybenzimidazoles containing aryl ether linkages[J].Journal of Polymer Science Part A:General Papers,1965,3(2):417-421.
[25]Korshak V V,Rusanov A L,Tugushi D S,et al.Tow-stage synthesis of poly(N-phenylbenzimidazoles)[J].Macromolcules,1972,5(6):807-812.
[26]Narayan T V L,Marvel C S.Polybenzimidazoles VI.Polybenzimidazoles containing aryl sulfone linkages[J].Journal of Polymer Science Part A-l:Polymer Chemistry,1967,5(5):1113-1118.
[27]Foster R T,Marvel C S.Polybenzimidazoles IV.Polybenzimidazoles containing aryl ether linkages[J].Journal of Polymer Science Part A:General Papers,1965,3(2):417-421.
[28]Yamaguchi I,Osakada K,Yamamoto T.A novel crowm ether stopping group for side chain polyrotaxane preparation of side chain polybenzimidazole rotaxane containing alkyl side chain ended by crown ether-oNa group[J].Macromolcules,2000,33(7):2315-2319.
[29]Still J K,Arnold F E.Polyquinoxalines.Ⅲ[J].Journal of Polymer Science Part A:Polymer Chemistry,1966,4(3):551-562.
[30]Jerry J H,Marvel CS.Benzimidazole polymers from aldehydes and tetraamines[J].Journal of Polymer Science Part A:Polymer Chemistry,1970,8(1):171-177.
[31]Smith Jr J G,Connell JW,Hergenrother P M.Poly(arylene ether benzoxazole)s[J].Polymer Preprints,1991,32(1):646-647.
[32]Twieg R T,Hedrick J L.Poly(aryl ether benzimidazoles)[J].Macromolecules,1996,29(32):7335-7341.
[33]Hedrick J L,Twieg R T,Matray T.Poly(aryl ether benzimidazoles)[J].American Chemical Society,Polym.Preper,1995,36(1):763-764.
[34]那辉,宛晶,倪宏伟等.含联苯结构聚醚酮酮共聚物和共混物的制备及性能研究[J].高等学校化学学报,1997,18(5):826-828.
[35]陆伟峰,虞鑫海.聚苯并咪唑树脂的合成及其应用[J].绝缘材料通讯,2000,5:5-9.
[36]Wittbecker E L,Morgen P W.Interfacial polycondensation.Ⅰ[J].Journal of Polymer Science Part A:Polymer Chemistry,1959,40(137):289-297.
[37]Neuse E W,Loonat M S.Tow-stage polybenzimidazole synthesis via poly(azonethine)intermediztes[J].Macromolecules,1983,16(1):128-136.
[38]Neuse E W,Loonat M S,Rabilloud G.Carboranylene-bridged poly(benzimidazole).Macromolecules,1986,19(2):481-484.
[39]Iwakura Y,Uno K,Imai Y.Polyphenylenebenzimidazoles[J].Journal of Polymer Science Part A:General papers,1964,2(6):2605-2615.
[40]Kim S H,Pearce E M,Kwei T K.The synthesis of a precursor of polybenzimidazole(PBI)and blends with polyamic acid(PAA)[J].Journal of Polymer Science Part A:Polymer Chemistry,1993,31(13):3167-3180.
[41]Frank W.Harris,Byung H.Ahh,et al.Synthesis of polybenzimidazoles via aromatic nucleophilic substitution reations of self-polymerizable(A-B) monomers[J].Polymer,1993,34(14):3083-3095.
[42]Richard W T,Collins G R,Sekin T,et al.Synthesis of 2,2-bis[4-(3,4-diaminophenoxy)phenyl]propane and its polymerization[J].Macromolecules,1992,25(4):1207-1213.
[43]Dippel T,Kreuer K D,Lasseques J C,et al.Proton conductivity in fused phosphoric acid;a 1H/31P PFG-NMR and QNS study[J].Solid State Ionics,1993,61(17):41-46.
[44]Onorato F J,Sansone M J,French S M,et al.Proceess for producing polybenzimidazole pastes and gels for use in fuel cells:WO,9904445[P].1999,02,08.
[45]宋才生,蔡明中,周丽云.低温溶液缩聚合成聚芳醚酮酮的研究[J].高分子学报,1995,1:99-103.
[46]Dale L B,Goldberg J,Ducray D,et al.Higher order iminodiacetic acid libraries for probing protein-protein interactions[J].Bioorganic & Medicinal Chemistry,1998,6(8):1347-1378.
[47]Wainright J S,Wang J T,Weng D,et al.Rutherford backscattering studies of polypyrrole films[J].Journal of The Electrochemical Society,1995,142(2):379-383.
[48]Fontanella J J,Wintersgill M C,Wainright J S,et al.High pressure electrical conductivity studies of acid doped polybenzimidazole[J].Electrochimica Acta,1998,43(10):1289-1394.
[49]Savadogo O.Surface chemistry and electrocatalytic of the HER on nickel modified with heteropolyacids[J].Journal of Electrochemical Society,1992,139(4):1082-1087.
[50]Kawahara M,Rikukawa M,Sanui K.Relationship between absorbed water and proton conductibity in sulfopropylated poly(benzimidazole)[J].Polymers for Advanced Technologies,2000,11(8):544-547.
[51]Glipa X,Bonnet B,Mula B,et al.Investigation of the conduction properties of phosphoric and sulfuric acid doped polybenzimidazole[J].Journal of Materials Chemistry,1999,9:3045-3049.
[52]Kawahara M,Morita J,Rikuawa M,Sanui B,et al.Synthesis an proton conductivity of thermally stable polymer electrolyte:poly(benzimidazole) complexes with strong acid molecules[J].Electrochimica Acta,2000,45(8):1395-1398.
[53]Pu H,Meyer W.H,Wegner G,Proton transport in polybenzimidazole blended with H3P04 or H2S04[J].Journal of Polymer Science Part B:Polymer Physics,2002,40(7):663-669.
[54]AkitaH,Ichikawa M,Nosaki K,et al.Solid polymer electrolytes:US,6124060[P],2000,09,26.
[55]Glipa X,Bonner B,Jones J,et al.On the doping of sulfonated polybenzimidazole with strong bases[J].Solid state Ionics,2001,145(1-4):61-68.
[56]Bouchet R,Siebert E.Proton conduction in acid doped polybenzimidazole[J].Solid state Ionics,1999,118(3-4):287-299.
[57]Radnaeva L D,Mognonov D M,Batotsayrenova A L,et al.Synthesis and investigation of poly(benzimidazole imides)[J].Acta Polyerica,1988,39(8):437-440.
[58]Banihashemi A,Fariborz A.Synthesis and characterization of new thermally stable polybenzimidazoles and poly(amide-benzimidazole)s[J].European Polymer Journal,2002,38(10):2119-2124.
[59]Berreda M,Anbaous Z,Lajrhed N,et al.Synthesis,characterization and studies fo heat-resistant poly(ether benzimidazole)senzimidazole)s[J].Chemistry of Mateials,1997,9(9):1983-1993.
[60]Berrda M,Carriere F,Abboud Y,et al.Peparation and characterization of new soluble enzimidazole-imide copolymers[J].Journal of Materials Chemistry,2002,12:3551-3559.
[61]Scariah K J,Krishnumarth V N,Rao K V C,et al.Synthesis and properties of new polybenzimidzaoles and N-phenyl polybenzimidazoles with flexibilizing spacers on the polymer backbone[J].Journal of Polymer Science Part A:Polymer Chemistry,1987,25(10):2675-2687.
[62]Izyneev A A,Varga I,Novak I S,et al.Synthesis and investigation of polyheteroarylenes with benzimidazole cycles[J].Acta Polyerica,1988,39(8):429-431.
[63]Korshak V V,Rusanov A L,Tugushi D S,et al.Two-stage synthesis of poly(N-phenybenzimidazoles)[J].Macromolecules.1972,5(6):807-812.
[64]Swith J G,Connell J W,Hergenrother P M.Synthesis and properties of polytarylene ether(N-arylene benzimidazole)s]s[J].Journal of Polymer Science Part A:Polymer Chemistry,1993,31(12):3099-3108.
[65]卿胜波,黄卫,颜德岳.耐高温磺化聚苯并咪唑的合成与表征[J].高等学校化学学报,2005,26(11):2145-2148.
[66]Mikroyannidis J A.Synthesis and characterization of soluble,Photoluminescent polyamides,Polyesters and polyethers containing 9,10-Di(4-biphenylyl)anthracene segments in the main chain[J].Polymer,2000,41(23):8193-8204.
[67]Lin J,Sherrington D C.Recent developments in the synthesis,Thermostability and Liquid crystal properties of aromatic polyamides[J].Advance Polymer Science,1994,111:177-219.
[68]Hongjie Xu,Kangcheng Chen,iiaoxia Guo,et al.Synthesis of hyperbranched polybenzimidazoles and their membrane formation[J].Journal of Membrane Science,2007,288(2):255-260.
[69]Cheng L,XiGao J,Mao S Z.Aromatic polyamides derived from unsymmetrial diamines containing the phthalazinone moiety[J].Polymer,2002,40(23):3489-3496.
[70]Mikroyannidis J A,Solube and fusible polyamides and polyimides containing pyrazoline moieties and their crosslinking to heat-resistant resins.Journal of Polymer Science Part A:Polymer Chemistry,1997,35(8):1353-1361.
[71]Imai Y,Maldar N N,Kakimoto M.Synthesis and characterization of souble polyamides from 2,5-bis(4-aminophenyl)-3,4-diphenylthiophene and aromatic tetracarboxylic dianhydrides[J].Journal of Polymer Science:Polymer Chemistry Edition,1984,22(9):2189-2196.
[72]Liou G S,Maruyama M,Kakimoto M,Imai Y.Preparation and properties of new soluble aromatic polyamides from 2,2'-bis(4-aminophenyl)biphenyl and aromatic dicarboxylic acids[J].Journal of Polymer Science Part A:Polymer Chemistry,1998,36(12):2029-2035.
[73]蹇锡高,孟跃忠,郑海滨等.含二氮杂萘酮结构的聚醚砜及制备法:中国,931091802[P].1993,07,26.
[74]尚蕾,蹇锡高,兰建武,等.含二氮杂萘酮结构耐热胶粘剂的研究[J].粘接,2002,23(3):1-3.
[75]兰建武,蹇锡高,王国庆,等.聚芳醚砜酮纤维的热性能[J].合成纤维工业,2003,26(2):24-26.
[76]王桂梅,蹇锡高,廖功雄,等.玻纤增强PPESK复合材料及其性能研究[J].中国塑料,2004,18(2):40-43.
[77]Gao Y,Robertson G P,Guiver M D et al.Synthesis and characterization of sulfonated poly(phthalazinone ether ketone) for proton exchange membrane materials[J].Journal of Polymer Science Part A:Polymer Chemistry,2003,41(4):497-507.
[78]Jian X G,Dai Y,Zeng L,et al.Application of poly(phthalazinone ether sulfone ketone)s to gas membrane separation[J].Journal of Applied Polymer Science,1999,71(14):2385-2390.
[79]蹇锡高,王瑞玲,朱秀玲,等.新型可溶性聚芳酰胺及其共聚物的合成与性能研究[J].高分子学报,2001,5:576-579.
[80]朱秀玲,蹇锡高,王瑞玲,等.苯取代杂萘联苯型聚芳酰胺的合成与表征及性能[J].高分子学报,2002,1:83-87.
[81]朱秀玲,蹇锡高,卢冶,等.含3-甲基苯基-2,3-二氮杂萘-1-酮结构聚醚酰胺的合成、表征与性能[J].高等学校化学学报,2003,24(2):355-358.
[82]Zhu X L,Jian X G.Soluble aromatic poly(ether amide)s containing aryl-,alkyl-,and chloro-substituted phthalazinone segments.Journal of Polymer Science Part A:Polymer Chemistry,2004,42(9):2026-2030.
[83]朱秀玲,卢冶,李建丰等.含杂萘类三联苯结构聚芳酰胺酰亚胺合成与性能[J].大连理工大学学报,2002,42(7):424-427.
[84]王锦艳,肖树德,蹇锡高等.含3,5-二甲基二氮杂萘酮联苯结构聚醚酰亚胺的合成与性能[J].高等学校化学学报,2003,24(3):555-558.
[85]Wang J Y,Liao G X,Liu C et al.Poly(ether imide)s derived from phthalazinone-containing dianhydrides[J].Journal of Polymer Science Part A:Polymer Chemistry,2004,42(24):6089-6097.
[86]高红昌,方晓雯,张涛等.1,2-二氢-4-(4-羟基苯基)(2H)二氮杂萘-1-酮的NMR谱研究[J].波谱学杂志,2001,18(4):343-349.
[87]蹇锡高,朱秀玲,陈连周.二氮杂萘酮联苯型聚芳醚聚合机理的探讨[J].大连理工大学学报,1999,39(50):629-634.
[88]Y F Wang,M Paventi,K P Chan,et al.Synthesis,characterization and ring-opening polymerization of novel high Tg macrocyclic oligomers based on 1,2-dihydro-4-(4-hydroxyphenyl)-(2H)-phthalazin-l-one[J].Journal of Polymer Science Part A:Polymer Chemistry,1996,34(12):2135-2148.
[89]S Yoshida,A S Hay.Synthesis of all-aromatic phthalazinone-containing polymers by a novel C-N coupling reaction[J].Macromolecules,1997,30(8):2254-2261.
[90]Hedberg F L,Marvel C S.A new single-step process for polybenzimidazole synthesis[J].Journal of Polymer Science Part A:Polymer Chemistry Ediition,1974,12(8):1823-1828.
[91]何继敏,薛平,何亚东.超高分子量聚乙烯性能及应用[J].工程塑料应用,1996,24(5):55-56.
[92]杨炳超,肖长发,安树林,贾广霞,聚丙烯酯/醋酸纤维素共混纤维亲水性研究[J].合成纤维,2007,5:23-26..
[93]邹新禧.超强吸水剂[M].北京:化工工业出版社,2002.
[94]孙克时,李志强,张淑玲等.水溶液共聚法合成耐盐性高吸水性树脂[J].化学与粘合,2000,3:1005-1007.
[2]Steck E A,Nachold F C,Ewing G W.Absorption spectra of heterocyclic compounds.Ⅲ.Some Benzimidazole Derivatives[J].Jourmal of the American Chemical Society,1948,70(10):3406-3410.
[3]Anthony B C,Edward C C,Thomas C B,et al.Polymerization and spinning of PBI[J].Journal of Polymer Science Part C:Polymer Symposia,1972,19(1):49-64.
[4]刘志刚,傅秦生,焦平坤,等。CFCs替代工质筛选的热力学原则[C].全国高等学校工程热物理第四届学术会议论文集.杭州:浙江大学出版社,1992,73-76.
[5]Cassidy P E.Thermally stable polymers,synthesis and properties[M].New York:Marcel Dekker,1980.
[6]Meisenheimer J and Wieger B.Mitteilung aus dem Ⅱ.Chemischen Institue der Universitat Budapest Uber N-Vinylbenzimidazole[J].Journal fur Praktische chemie,1921,102(1):45-62.
[7]Overberger C G,Pierre T St,Vorchheimer N,et al.The esterolytic catalysis of Poly-4(5)-vinylimidazole and Poly-5(6)-vinylbenzimidazole[J].Jourmal of the American Chemical Society,1963,85(20):3513-3515.
[8]Deborah J.Jones,Jacques Rozi(?)re.Recent advances in the functionalisation of polybenzimidazole and polyetherketone for fuel cell applications[J].Journal of Membrane Science,2001,185(1):41-58.
[9]Price J A,Corm S.Polymerizable compositions comprising 2-vinylbenzimidazole and polymerization products:US,2606175[P].1952,08,05.
[10]Vogel H,Marvel C S.Polybenzimidazoles,new thermally stable polymers[J].Journal of Polymer Science Part A:General Papers,1961,50(154):511-539.
[11]Brinker K C,Robinson I M.Polybenzimidazoles:US,2895948[P].1995,10,28.
[12]Levine H H,Calif L J.Fusible Polybenzimidzaole polymer product and process:US,3533879[P].1970,10,13.
[13]Brinegar W C.Production of semipermeable polubenzimidazole membranes:US,3841492[P].1974,10,15.
[14]Powers E J,Hassinger W P,Heights B,et al.Process for the dyeing of polybenzimidole fibers with anionic dyestuffs:US,3942950[P].1997,03,09.
[15]Tan M,N.J R P.Process for producing high-strength,ultralow dening polybenzimidazole(PBI) filaments:US,4263245[P].1981,04,23.
[16]Stuetz D E,N.J W.Production of activated carbon fibers from acid contacted polybenzimidazole fibrous material:US,4460708.1984,07,17.
[17]Summa G D,MO R.Positive retraction trolley stop for power and free conveyors:US,4898099[P].1990,02,06.
[18]Sansone M J,N.J B H.Process for the production of polybenzimidazole ultrafiltration membranes:US,4693824[P].1987,09,05.
[19]Marikar Y M F,Plains S,Besso M M,et al.Process for preparing electrically conductive shaped articles from polybenzimidazoles:US 4868008[P].1989,09,19.
[20]Wadhwa L,Plainfield N,Bitritto M,et al.Fabrication of high performance polybenzimidazole films:US,4927909[P].1987,09,18.
[21]Sansong M J,Height B,Onorato F J,et al.Acid-modified polybenzimidazole fuel cell elements:US,5599639[P].1995,10,27.
[22]Plummer L.Marvel C S.Polybenzimidazoles Ⅲ[J].Journal of Polymer Science Part A:General Paper 1964,2(6):2559-2569.
[23]Tsur Y,Levine H H,Levy M.Effects of structure on properties of some new aromatic-aliphatic polybenzimidazoles[J].Journal of Polymer Science:Polymer Chemistry Edition,1974,12(7):1515-1529.
[24]Foster R T,Marvel C S.Polybenzimidazoles Ⅳ.Polybenzimidazoles containing aryl ether linkages[J].Journal of Polymer Science Part A:General Papers,1965,3(2):417-421.
[25]Korshak V V,Rusanov A L,Tugushi D S,et al.Tow-stage synthesis of poly(N-phenylbenzimidazoles)[J].Macromolcules,1972,5(6):807-812.
[26]Narayan T V L,Marvel C S.Polybenzimidazoles VI.Polybenzimidazoles containing aryl sulfone linkages[J].Journal of Polymer Science Part A-l:Polymer Chemistry,1967,5(5):1113-1118.
[27]Foster R T,Marvel C S.Polybenzimidazoles IV.Polybenzimidazoles containing aryl ether linkages[J].Journal of Polymer Science Part A:General Papers,1965,3(2):417-421.
[28]Yamaguchi I,Osakada K,Yamamoto T.A novel crowm ether stopping group for side chain polyrotaxane preparation of side chain polybenzimidazole rotaxane containing alkyl side chain ended by crown ether-oNa group[J].Macromolcules,2000,33(7):2315-2319.
[29]Still J K,Arnold F E.Polyquinoxalines.Ⅲ[J].Journal of Polymer Science Part A:Polymer Chemistry,1966,4(3):551-562.
[30]Jerry J H,Marvel CS.Benzimidazole polymers from aldehydes and tetraamines[J].Journal of Polymer Science Part A:Polymer Chemistry,1970,8(1):171-177.
[31]Smith Jr J G,Connell JW,Hergenrother P M.Poly(arylene ether benzoxazole)s[J].Polymer Preprints,1991,32(1):646-647.
[32]Twieg R T,Hedrick J L.Poly(aryl ether benzimidazoles)[J].Macromolecules,1996,29(32):7335-7341.
[33]Hedrick J L,Twieg R T,Matray T.Poly(aryl ether benzimidazoles)[J].American Chemical Society,Polym.Preper,1995,36(1):763-764.
[34]那辉,宛晶,倪宏伟等.含联苯结构聚醚酮酮共聚物和共混物的制备及性能研究[J].高等学校化学学报,1997,18(5):826-828.
[35]陆伟峰,虞鑫海.聚苯并咪唑树脂的合成及其应用[J].绝缘材料通讯,2000,5:5-9.
[36]Wittbecker E L,Morgen P W.Interfacial polycondensation.Ⅰ[J].Journal of Polymer Science Part A:Polymer Chemistry,1959,40(137):289-297.
[37]Neuse E W,Loonat M S.Tow-stage polybenzimidazole synthesis via poly(azonethine)intermediztes[J].Macromolecules,1983,16(1):128-136.
[38]Neuse E W,Loonat M S,Rabilloud G.Carboranylene-bridged poly(benzimidazole).Macromolecules,1986,19(2):481-484.
[39]Iwakura Y,Uno K,Imai Y.Polyphenylenebenzimidazoles[J].Journal of Polymer Science Part A:General papers,1964,2(6):2605-2615.
[40]Kim S H,Pearce E M,Kwei T K.The synthesis of a precursor of polybenzimidazole(PBI)and blends with polyamic acid(PAA)[J].Journal of Polymer Science Part A:Polymer Chemistry,1993,31(13):3167-3180.
[41]Frank W.Harris,Byung H.Ahh,et al.Synthesis of polybenzimidazoles via aromatic nucleophilic substitution reations of self-polymerizable(A-B) monomers[J].Polymer,1993,34(14):3083-3095.
[42]Richard W T,Collins G R,Sekin T,et al.Synthesis of 2,2-bis[4-(3,4-diaminophenoxy)phenyl]propane and its polymerization[J].Macromolecules,1992,25(4):1207-1213.
[43]Dippel T,Kreuer K D,Lasseques J C,et al.Proton conductivity in fused phosphoric acid;a 1H/31P PFG-NMR and QNS study[J].Solid State Ionics,1993,61(17):41-46.
[44]Onorato F J,Sansone M J,French S M,et al.Proceess for producing polybenzimidazole pastes and gels for use in fuel cells:WO,9904445[P].1999,02,08.
[45]宋才生,蔡明中,周丽云.低温溶液缩聚合成聚芳醚酮酮的研究[J].高分子学报,1995,1:99-103.
[46]Dale L B,Goldberg J,Ducray D,et al.Higher order iminodiacetic acid libraries for probing protein-protein interactions[J].Bioorganic & Medicinal Chemistry,1998,6(8):1347-1378.
[47]Wainright J S,Wang J T,Weng D,et al.Rutherford backscattering studies of polypyrrole films[J].Journal of The Electrochemical Society,1995,142(2):379-383.
[48]Fontanella J J,Wintersgill M C,Wainright J S,et al.High pressure electrical conductivity studies of acid doped polybenzimidazole[J].Electrochimica Acta,1998,43(10):1289-1394.
[49]Savadogo O.Surface chemistry and electrocatalytic of the HER on nickel modified with heteropolyacids[J].Journal of Electrochemical Society,1992,139(4):1082-1087.
[50]Kawahara M,Rikukawa M,Sanui K.Relationship between absorbed water and proton conductibity in sulfopropylated poly(benzimidazole)[J].Polymers for Advanced Technologies,2000,11(8):544-547.
[51]Glipa X,Bonnet B,Mula B,et al.Investigation of the conduction properties of phosphoric and sulfuric acid doped polybenzimidazole[J].Journal of Materials Chemistry,1999,9:3045-3049.
[52]Kawahara M,Morita J,Rikuawa M,Sanui B,et al.Synthesis an proton conductivity of thermally stable polymer electrolyte:poly(benzimidazole) complexes with strong acid molecules[J].Electrochimica Acta,2000,45(8):1395-1398.
[53]Pu H,Meyer W.H,Wegner G,Proton transport in polybenzimidazole blended with H3P04 or H2S04[J].Journal of Polymer Science Part B:Polymer Physics,2002,40(7):663-669.
[54]AkitaH,Ichikawa M,Nosaki K,et al.Solid polymer electrolytes:US,6124060[P],2000,09,26.
[55]Glipa X,Bonner B,Jones J,et al.On the doping of sulfonated polybenzimidazole with strong bases[J].Solid state Ionics,2001,145(1-4):61-68.
[56]Bouchet R,Siebert E.Proton conduction in acid doped polybenzimidazole[J].Solid state Ionics,1999,118(3-4):287-299.
[57]Radnaeva L D,Mognonov D M,Batotsayrenova A L,et al.Synthesis and investigation of poly(benzimidazole imides)[J].Acta Polyerica,1988,39(8):437-440.
[58]Banihashemi A,Fariborz A.Synthesis and characterization of new thermally stable polybenzimidazoles and poly(amide-benzimidazole)s[J].European Polymer Journal,2002,38(10):2119-2124.
[59]Berreda M,Anbaous Z,Lajrhed N,et al.Synthesis,characterization and studies fo heat-resistant poly(ether benzimidazole)senzimidazole)s[J].Chemistry of Mateials,1997,9(9):1983-1993.
[60]Berrda M,Carriere F,Abboud Y,et al.Peparation and characterization of new soluble enzimidazole-imide copolymers[J].Journal of Materials Chemistry,2002,12:3551-3559.
[61]Scariah K J,Krishnumarth V N,Rao K V C,et al.Synthesis and properties of new polybenzimidzaoles and N-phenyl polybenzimidazoles with flexibilizing spacers on the polymer backbone[J].Journal of Polymer Science Part A:Polymer Chemistry,1987,25(10):2675-2687.
[62]Izyneev A A,Varga I,Novak I S,et al.Synthesis and investigation of polyheteroarylenes with benzimidazole cycles[J].Acta Polyerica,1988,39(8):429-431.
[63]Korshak V V,Rusanov A L,Tugushi D S,et al.Two-stage synthesis of poly(N-phenybenzimidazoles)[J].Macromolecules.1972,5(6):807-812.
[64]Swith J G,Connell J W,Hergenrother P M.Synthesis and properties of polytarylene ether(N-arylene benzimidazole)s]s[J].Journal of Polymer Science Part A:Polymer Chemistry,1993,31(12):3099-3108.
[65]卿胜波,黄卫,颜德岳.耐高温磺化聚苯并咪唑的合成与表征[J].高等学校化学学报,2005,26(11):2145-2148.
[66]Mikroyannidis J A.Synthesis and characterization of soluble,Photoluminescent polyamides,Polyesters and polyethers containing 9,10-Di(4-biphenylyl)anthracene segments in the main chain[J].Polymer,2000,41(23):8193-8204.
[67]Lin J,Sherrington D C.Recent developments in the synthesis,Thermostability and Liquid crystal properties of aromatic polyamides[J].Advance Polymer Science,1994,111:177-219.
[68]Hongjie Xu,Kangcheng Chen,iiaoxia Guo,et al.Synthesis of hyperbranched polybenzimidazoles and their membrane formation[J].Journal of Membrane Science,2007,288(2):255-260.
[69]Cheng L,XiGao J,Mao S Z.Aromatic polyamides derived from unsymmetrial diamines containing the phthalazinone moiety[J].Polymer,2002,40(23):3489-3496.
[70]Mikroyannidis J A,Solube and fusible polyamides and polyimides containing pyrazoline moieties and their crosslinking to heat-resistant resins.Journal of Polymer Science Part A:Polymer Chemistry,1997,35(8):1353-1361.
[71]Imai Y,Maldar N N,Kakimoto M.Synthesis and characterization of souble polyamides from 2,5-bis(4-aminophenyl)-3,4-diphenylthiophene and aromatic tetracarboxylic dianhydrides[J].Journal of Polymer Science:Polymer Chemistry Edition,1984,22(9):2189-2196.
[72]Liou G S,Maruyama M,Kakimoto M,Imai Y.Preparation and properties of new soluble aromatic polyamides from 2,2'-bis(4-aminophenyl)biphenyl and aromatic dicarboxylic acids[J].Journal of Polymer Science Part A:Polymer Chemistry,1998,36(12):2029-2035.
[73]蹇锡高,孟跃忠,郑海滨等.含二氮杂萘酮结构的聚醚砜及制备法:中国,931091802[P].1993,07,26.
[74]尚蕾,蹇锡高,兰建武,等.含二氮杂萘酮结构耐热胶粘剂的研究[J].粘接,2002,23(3):1-3.
[75]兰建武,蹇锡高,王国庆,等.聚芳醚砜酮纤维的热性能[J].合成纤维工业,2003,26(2):24-26.
[76]王桂梅,蹇锡高,廖功雄,等.玻纤增强PPESK复合材料及其性能研究[J].中国塑料,2004,18(2):40-43.
[77]Gao Y,Robertson G P,Guiver M D et al.Synthesis and characterization of sulfonated poly(phthalazinone ether ketone) for proton exchange membrane materials[J].Journal of Polymer Science Part A:Polymer Chemistry,2003,41(4):497-507.
[78]Jian X G,Dai Y,Zeng L,et al.Application of poly(phthalazinone ether sulfone ketone)s to gas membrane separation[J].Journal of Applied Polymer Science,1999,71(14):2385-2390.
[79]蹇锡高,王瑞玲,朱秀玲,等.新型可溶性聚芳酰胺及其共聚物的合成与性能研究[J].高分子学报,2001,5:576-579.
[80]朱秀玲,蹇锡高,王瑞玲,等.苯取代杂萘联苯型聚芳酰胺的合成与表征及性能[J].高分子学报,2002,1:83-87.
[81]朱秀玲,蹇锡高,卢冶,等.含3-甲基苯基-2,3-二氮杂萘-1-酮结构聚醚酰胺的合成、表征与性能[J].高等学校化学学报,2003,24(2):355-358.
[82]Zhu X L,Jian X G.Soluble aromatic poly(ether amide)s containing aryl-,alkyl-,and chloro-substituted phthalazinone segments.Journal of Polymer Science Part A:Polymer Chemistry,2004,42(9):2026-2030.
[83]朱秀玲,卢冶,李建丰等.含杂萘类三联苯结构聚芳酰胺酰亚胺合成与性能[J].大连理工大学学报,2002,42(7):424-427.
[84]王锦艳,肖树德,蹇锡高等.含3,5-二甲基二氮杂萘酮联苯结构聚醚酰亚胺的合成与性能[J].高等学校化学学报,2003,24(3):555-558.
[85]Wang J Y,Liao G X,Liu C et al.Poly(ether imide)s derived from phthalazinone-containing dianhydrides[J].Journal of Polymer Science Part A:Polymer Chemistry,2004,42(24):6089-6097.
[86]高红昌,方晓雯,张涛等.1,2-二氢-4-(4-羟基苯基)(2H)二氮杂萘-1-酮的NMR谱研究[J].波谱学杂志,2001,18(4):343-349.
[87]蹇锡高,朱秀玲,陈连周.二氮杂萘酮联苯型聚芳醚聚合机理的探讨[J].大连理工大学学报,1999,39(50):629-634.
[88]Y F Wang,M Paventi,K P Chan,et al.Synthesis,characterization and ring-opening polymerization of novel high Tg macrocyclic oligomers based on 1,2-dihydro-4-(4-hydroxyphenyl)-(2H)-phthalazin-l-one[J].Journal of Polymer Science Part A:Polymer Chemistry,1996,34(12):2135-2148.
[89]S Yoshida,A S Hay.Synthesis of all-aromatic phthalazinone-containing polymers by a novel C-N coupling reaction[J].Macromolecules,1997,30(8):2254-2261.
[90]Hedberg F L,Marvel C S.A new single-step process for polybenzimidazole synthesis[J].Journal of Polymer Science Part A:Polymer Chemistry Ediition,1974,12(8):1823-1828.
[91]何继敏,薛平,何亚东.超高分子量聚乙烯性能及应用[J].工程塑料应用,1996,24(5):55-56.
[92]杨炳超,肖长发,安树林,贾广霞,聚丙烯酯/醋酸纤维素共混纤维亲水性研究[J].合成纤维,2007,5:23-26..
[93]邹新禧.超强吸水剂[M].北京:化工工业出版社,2002.
[94]孙克时,李志强,张淑玲等.水溶液共聚法合成耐盐性高吸水性树脂[J].化学与粘合,2000,3:1005-1007.