多酮基聚芳醚酮及其单体合成与性能研究
|
摘要
随着高新技术的发展,对高性能特种工程塑料的需求与日俱增,对材料的综合性能特别是耐热性提出了更高的要求。在聚芳醚酮类树脂中由于酮基比醚键更具刚性,所以随着聚合物分子主链中酮基比例的增加,其耐热性也将进一步提高。本文从分子设计出发,合成含多酮基结构单元的芳二酰氯,并以此为单体合成系列主链含多酮基的聚芳醚酮聚合物,研究其结构与性能之间的关系,为开发综合性能优良的耐高温热塑性树脂及其工业化生产提供理论基础和实验依据。主要研究内容包括以下三个方面:
1.以甲苯和间苯二甲酰氯(IPC)为原料,经傅-克酰基化反应,制备高纯度的1,3-二(4-甲基苯甲酰基)苯(i-DMBB);以KMnO4/吡啶/水为氧化体系,将1,3-二(4-甲基苯甲酰基)苯(i-DMBB)氧化合成高纯度的1,3-二(4-甲羧基苯甲酰基)苯(i-DMBA);用氯化亚砜将羧基酰化,制得结构新型的芳二酰氯1,3-二(4-氯甲酰基苯甲酰基)苯(i-DMBC)。原料改为甲苯和对苯二甲酰氯(TPC),以同样方法制得1,4-二(4-氯甲酰基苯甲酰基)苯(p-DMBC)。经FT-IR、1H-NMR、元素分析及DSC分析表明:目标产物具有预期的结构和较高的纯度,可作为高性能高分子材料聚芳醚酮(PEK)、聚芳酯(PAR)及聚芳酰胺的单体及改性剂。
2.以合成的芳二酰氯1,3/1,4-二(4-氯甲酰基苯甲酰基)苯(i/p-DMBC)为单体,将其分别与4,4'-二苯氧基二苯砜(DPODPS)、1,3-二(4-苯氧基苯甲酰基)苯(i-DPOPKK)、1,4-二(4-苯氧基苯甲酰基)苯(p-DPOPKK)进行低温溶液共缩聚,合成系列主链含多酮基的新型聚芳醚酮。用FT-IR、1H-NMR、DSC、TGA、WAXD等技术对聚合物进行结构和性能表征,研究聚合物的结构与性能的关系。结果表明:增加聚合物主链中酮基的含量可提高其耐热等级,在合成的聚合物中,玻璃化转变温度Tg最高可达189℃、熔融温度Tm最高可达403℃,同时,间位取代苯基及四面体砜基结构的引入可适当降低Tm、改善溶解性,为开发综合性能优良的耐高温聚芳醚酮类树脂提供了依据;此外,聚合物中酮基比例的增大,使得其聚集态晶体结构也产生相应的变化,较易产生多晶型,在合成的聚合物中基本都存在FormⅠ和FormⅡ两种晶型。
3.用差示扫描量热法(DSC)及广角X-射线衍射(WAXD)技术较详细地研究了主链含多酮基的新型聚芳醚酮PEKKEKK-i-KK经过不同条件处理后树脂的结晶行为,从微观角度探讨聚芳醚酮类树脂结构与性能之间的关系,为聚芳醚酮类树脂的加工成型和性能的关系提供一定的依据。结果表明:多酮基聚芳醚酮聚合物中存在FormⅠ和FormⅡ两种晶型,FormⅡ较为不稳定,在一定条件下可转化为FormⅠ。通过等温诱导结晶、冷牵伸等方法可以改变聚合物中两种晶型的比例及得到较纯的FormⅠ晶型聚合物。
With the development of high-tech, the need for high-performance polymers grows day by day, and higher demand for their integrative property, especially the thermostability have been advanced. As for poly(aryl ether ketone)s(PEKs), the ketonic linkage and the ether linkage are contained, and the rigidity of the ketonic linkage is stronger than the ether linkage's, so the increasing ratio of the ketonic linkage in the macromolecule chain can make the polymers exhibit more excellent thermostability. In this paper, above all, two monomers have been successfully synthesised. Then PEKs based on them have been synthesised and characterized. Last, the relation between the structure and properties of the polymers have been studied. The main idea of this paper is followed.
1. 1,3-Di(4-methyl benzoyl)benzene(i-DMBB) was prepared by Friedel-Crafts electrophilic aromatic substitution reaction from isophthaloyl chloride (IPC) and toluene; i-DMBB was subsequently oxidated into intermediate, 1,3-di(4-carboxyl benzoyl)benzene(i-DMBA) in the presence of KMnO4 in the mixture solvent of pyridine and water; then the reaction of i-DMBA with sulfurous oxychloride yielded polymerization-grade monomer 1,3-di(4-chloro formyl benzoyl)benzene(i-DMBC). 1,4-di(4-chloro formylbenzoyl)benzene(p-DMBC) was obtained on condition that the reaction started with terephthaloyl chloride (TPC) and toluene. The products were characterized by FT-IR, 1H-NMR, elemental analysis and DSC. It was proved that high purified compounds had been obtained, and they can become monomers and remodeling reagents of high-performance polymers, such as poly(aryl ether ketone)(PEK), polyarylates(PAR) and aryl polyamide.
2. Novel poly(aryl ether ketone)s(PEKs) containing multi-ketonic linkage were prepared by low temperature solution polycondensation of i/p-DMBC with 4,4'-diphenoxydiphenylsolfone(DPODPS), 1,3-di(4-phenoxybenzoylbenzene (i-DPOPKK) and 1,4-di(4-phenoxybenzoyl)benzene(p-DPOPKK) in 1,2-dichloro -ethane(DCE) with the presence of AlCl3 and DMAc. The resulting polymers were characterized by various analytical techniques, such as FT-IR, 1H-NMR, DSC, TGA and WAXD. The relation between the structure and properties of the polymers had been studied. The results show that high molecular weight polymers have been readily obtained. With the increasing ratio of ketonic linkage in the macromolecule chain, the polymers exhibit excellent thermostability, such as the highest glass transition temperature(Tg) of the polymers is 189℃, the highest melting temperature(Tm) of the polymers is 403℃. At the same time, the introducing of the tetrahedral sulfonyl(-SO2-) and meta-phenyl substitution can make the Tm of the polymers decrease appropriately, and the solubility of the polymers is also improved. Furthermore, with the increasing ratio of ketonic linkage in the macromolecule chain, the structure of the polymers has changed , polymorphism is easily to be found. We have found two crystal types, FormⅠand FormⅡ, in the polymers via the analysis of WAXD and DSC.
3. The crystallization of poly(aryl ether ketone) containing multi-ketonic linkage, PEKKEKK-i-KK, was studied by differential scanning calorimetry(DSC) and wide-angle X-ray diffraction(WAXD). The relation between the structure and properties of the polymers has been studied in further from the microcosmic angle, and the evidence of processing and properities has been provided. The results show that there are two crystal types, FormⅠand FormⅡ, in the polymers, and the crystal type of FormⅠis more stable than the crystal type of FormⅡ. The ratio of FormⅠand FormⅡcan be changed by way of different treatment, such as induced crystallization of thermal treatment, elongation and so on. Moreover, the polymer, which just contains the crystal type of FormⅠ, can be obtained via elongation.
1.以甲苯和间苯二甲酰氯(IPC)为原料,经傅-克酰基化反应,制备高纯度的1,3-二(4-甲基苯甲酰基)苯(i-DMBB);以KMnO4/吡啶/水为氧化体系,将1,3-二(4-甲基苯甲酰基)苯(i-DMBB)氧化合成高纯度的1,3-二(4-甲羧基苯甲酰基)苯(i-DMBA);用氯化亚砜将羧基酰化,制得结构新型的芳二酰氯1,3-二(4-氯甲酰基苯甲酰基)苯(i-DMBC)。原料改为甲苯和对苯二甲酰氯(TPC),以同样方法制得1,4-二(4-氯甲酰基苯甲酰基)苯(p-DMBC)。经FT-IR、1H-NMR、元素分析及DSC分析表明:目标产物具有预期的结构和较高的纯度,可作为高性能高分子材料聚芳醚酮(PEK)、聚芳酯(PAR)及聚芳酰胺的单体及改性剂。
2.以合成的芳二酰氯1,3/1,4-二(4-氯甲酰基苯甲酰基)苯(i/p-DMBC)为单体,将其分别与4,4'-二苯氧基二苯砜(DPODPS)、1,3-二(4-苯氧基苯甲酰基)苯(i-DPOPKK)、1,4-二(4-苯氧基苯甲酰基)苯(p-DPOPKK)进行低温溶液共缩聚,合成系列主链含多酮基的新型聚芳醚酮。用FT-IR、1H-NMR、DSC、TGA、WAXD等技术对聚合物进行结构和性能表征,研究聚合物的结构与性能的关系。结果表明:增加聚合物主链中酮基的含量可提高其耐热等级,在合成的聚合物中,玻璃化转变温度Tg最高可达189℃、熔融温度Tm最高可达403℃,同时,间位取代苯基及四面体砜基结构的引入可适当降低Tm、改善溶解性,为开发综合性能优良的耐高温聚芳醚酮类树脂提供了依据;此外,聚合物中酮基比例的增大,使得其聚集态晶体结构也产生相应的变化,较易产生多晶型,在合成的聚合物中基本都存在FormⅠ和FormⅡ两种晶型。
3.用差示扫描量热法(DSC)及广角X-射线衍射(WAXD)技术较详细地研究了主链含多酮基的新型聚芳醚酮PEKKEKK-i-KK经过不同条件处理后树脂的结晶行为,从微观角度探讨聚芳醚酮类树脂结构与性能之间的关系,为聚芳醚酮类树脂的加工成型和性能的关系提供一定的依据。结果表明:多酮基聚芳醚酮聚合物中存在FormⅠ和FormⅡ两种晶型,FormⅡ较为不稳定,在一定条件下可转化为FormⅠ。通过等温诱导结晶、冷牵伸等方法可以改变聚合物中两种晶型的比例及得到较纯的FormⅠ晶型聚合物。
With the development of high-tech, the need for high-performance polymers grows day by day, and higher demand for their integrative property, especially the thermostability have been advanced. As for poly(aryl ether ketone)s(PEKs), the ketonic linkage and the ether linkage are contained, and the rigidity of the ketonic linkage is stronger than the ether linkage's, so the increasing ratio of the ketonic linkage in the macromolecule chain can make the polymers exhibit more excellent thermostability. In this paper, above all, two monomers have been successfully synthesised. Then PEKs based on them have been synthesised and characterized. Last, the relation between the structure and properties of the polymers have been studied. The main idea of this paper is followed.
1. 1,3-Di(4-methyl benzoyl)benzene(i-DMBB) was prepared by Friedel-Crafts electrophilic aromatic substitution reaction from isophthaloyl chloride (IPC) and toluene; i-DMBB was subsequently oxidated into intermediate, 1,3-di(4-carboxyl benzoyl)benzene(i-DMBA) in the presence of KMnO4 in the mixture solvent of pyridine and water; then the reaction of i-DMBA with sulfurous oxychloride yielded polymerization-grade monomer 1,3-di(4-chloro formyl benzoyl)benzene(i-DMBC). 1,4-di(4-chloro formylbenzoyl)benzene(p-DMBC) was obtained on condition that the reaction started with terephthaloyl chloride (TPC) and toluene. The products were characterized by FT-IR, 1H-NMR, elemental analysis and DSC. It was proved that high purified compounds had been obtained, and they can become monomers and remodeling reagents of high-performance polymers, such as poly(aryl ether ketone)(PEK), polyarylates(PAR) and aryl polyamide.
2. Novel poly(aryl ether ketone)s(PEKs) containing multi-ketonic linkage were prepared by low temperature solution polycondensation of i/p-DMBC with 4,4'-diphenoxydiphenylsolfone(DPODPS), 1,3-di(4-phenoxybenzoylbenzene (i-DPOPKK) and 1,4-di(4-phenoxybenzoyl)benzene(p-DPOPKK) in 1,2-dichloro -ethane(DCE) with the presence of AlCl3 and DMAc. The resulting polymers were characterized by various analytical techniques, such as FT-IR, 1H-NMR, DSC, TGA and WAXD. The relation between the structure and properties of the polymers had been studied. The results show that high molecular weight polymers have been readily obtained. With the increasing ratio of ketonic linkage in the macromolecule chain, the polymers exhibit excellent thermostability, such as the highest glass transition temperature(Tg) of the polymers is 189℃, the highest melting temperature(Tm) of the polymers is 403℃. At the same time, the introducing of the tetrahedral sulfonyl(-SO2-) and meta-phenyl substitution can make the Tm of the polymers decrease appropriately, and the solubility of the polymers is also improved. Furthermore, with the increasing ratio of ketonic linkage in the macromolecule chain, the structure of the polymers has changed , polymorphism is easily to be found. We have found two crystal types, FormⅠand FormⅡ, in the polymers via the analysis of WAXD and DSC.
3. The crystallization of poly(aryl ether ketone) containing multi-ketonic linkage, PEKKEKK-i-KK, was studied by differential scanning calorimetry(DSC) and wide-angle X-ray diffraction(WAXD). The relation between the structure and properties of the polymers has been studied in further from the microcosmic angle, and the evidence of processing and properities has been provided. The results show that there are two crystal types, FormⅠand FormⅡ, in the polymers, and the crystal type of FormⅠis more stable than the crystal type of FormⅡ. The ratio of FormⅠand FormⅡcan be changed by way of different treatment, such as induced crystallization of thermal treatment, elongation and so on. Moreover, the polymer, which just contains the crystal type of FormⅠ, can be obtained via elongation.
引文
[1]Bonner H W. USP, 3065205. 1962
[2]Olah G A, et al. Friedel-Crafts and Related Reactions. John Wiley and Sons Ltd London, 1964, 3: 1014-1020
[3]Charles E B. USP, 3516966. 1970
[4]Chang Ike Y. SAMPE Quarterly, 1988, 19(4): 29-34
[5]曹俊奎,苏文成,吴忠文.刚性链嵌段共聚物的研究(Ⅱ) -含双酚S的聚醚醚酮共聚物合成与性能[J].高分子学报, 1994, 4: 477-481
[6]曹俊奎等.聚醚醚酮/聚醚砜嵌段共聚物的动态力学行为[J].高等学校化学学报, 1994, 14(5): 738-740
[7]曹俊奎,黄智华,吴忠文.聚醚醚酮分子结构对流动性和热性能的影响[J].高分子学报, 1994, 1: 27-29
[8]曹俊奎等.刚性链嵌段共聚物的研究(Ⅲ) -PEEK/HTA有规嵌段共聚物的合成与性能[J].高等学校化学学报, 1994, 15(1): 145-149
[9]曹俊奎等.刚性链嵌段共聚物的研究(Ⅳ)-聚醚醚酮/苯酞圈型聚芳醚砜有规嵌段共聚物的合成与部分性能[J].高等学校化学学报, 1994, 15(2): 303-307
[10]张万金,吴忠文等.高性能聚芳醚酮的合成与性能(Ⅰ) -对苯二酚、联苯二酚、4,4'-二氟二苯酮三元共聚体系[J].高等学校化学学, 1993, 14(5): 738-740
[11]郭纯孝,张万金,牛力,蒋大振,黄东律.含二联苯结构聚醚醚酮的微结构及磺化改性的性质研究[J].高等学校化学学报, 1994, 15(2): 240-243
[12]张万金,吴忠文等.一种含联苯的聚醚醚酮酮的合成与表征[J].应用化学, 1993, 10(6): 106-108
[13]王军佐.聚芳醚酮类高聚物的合成与热性能研究[J].高等学校化学学报, 1993, 14(9): 1308-1311
[14]苑晶,张万金,那辉等.联苯聚醚醚酮酮的合成与性能研究[J].高等学校化学学报, 1994, 15(5): 763-766
[15]张海春,陈天禄.一步法合成带有酞侧基的聚芳醚砜[P].中国专利, 85108751. 1985
[16]李滨耀,庄国庆.酞侧基聚芳醚砜和聚芳醚酮共混物的高温流变行为[J].高分子学报, 1994, 3: 289-291
[17]蹇锡高, Hay AS,郑海滨.含二氮杂萘酮结构的聚醚砜及制备法[P].中国专利, CN93109180.2. 1993-07-26
[18]孟跃中,蹇锡高,郑海滨等.杂环取代联苯型聚醚酮的合成与表征[J].高分子材料科学与工程, 1994, 10(2): 22-25
[19]孟跃中,蹇锡高等.杂环联苯型聚芳醚酮热稳定性研究[J].高分子材料科学与工程, 1994, 10(6): 85-88
[20]宋才生等.亲电聚合路线合成聚芳醚酮砜的研究[J].高分子材料, 1993, 3: 2-5
[21]蔡明中等.亲电聚合路线合成聚醚醚酮酮砜的研究[J].精细石油化工, 1993, 950: 15-18
[22]蔡明中,宋才生,周丽云.亲电聚合路线合成含氯取代基的聚芳醚酮酮的研究[J].化学世界, 1993, 10: 486-488
[23]宋才生等.低温溶液缩聚合成聚芳醚酮酮的研究[J].高分子学报, 1995, 1: 99-102
[24]盛寿日,蔡明中,宋才生.含间苯基聚醚酮醚酮酮的合成和性能研究[J].高分子学报, 1999, 4: 490-493
[25]黎苇,蔡明中,宋才生. 4,4'-二苯氧基二苯砜、4,4'-二苯氧基二苯酮、对苯二甲酰氯三元共聚物的合成[J].应用化学, 2002, 7: 653-656
[26]谌烈.含双邻位甲基聚芳醚砜和聚芳醚酮的合成与性能研究[D]: [硕士学位论文].江西:江西师范大学化学化工学院, 2004
[27]童永芬.聚芳醚砜以及聚芳醚酮的合成与性能研究[D]: [硕士学位论文].江西:江西师范大学化学化工学院, 2004
[28]钟鸣.聚芳醚酮和聚芳醚砜的合成与改性研究[D]: [硕士学位论文].江西:江西师范大学化学化工学院, 2006
[29]吴方娟.聚芳醚砜亚胺酮的合成与表征[D]: [硕士学位论文].江西:江西师范大学化学化工学院, 2007
[30]戴润英.聚芳醚酮嵌段共聚合成及其结构与性能研究[D]: [硕士学位论文].江西:江西师范大学化学化工学院, 2008
[31]黄红.新型耐高温聚芳醚酮及其单体的合成与性能研究[D]: [硕士学位论文].江西:江西师范大学化学化工学院, 2008
[32]Hoffmann U, Klapper M, Mül K. Phase-transfer catalyzed synthesis of poly(etherketone)s. Polymer Bulletin, 2004, 30(5): 481-488
[33]刘彦军,蹇锡高,刘圣军.含二氮杂萘酮结构聚醚酮的合成与表征[J].高分子学报, 1999, 1: 37-41
[34]高燕,蹇锡高.含二氮杂萘酮和萘结构聚芳醚酮的研究[J].高分子材料科学与工程, 2001, 17(3): 160-162
[35]李秀华,孟跃中,蹇锡高.含二氮杂萘酮结构的新型共聚醚酮的合成及性能[J].高分子材料科学与工程, 1998, 14(4): 37-39
[36]陈连周,蹇锡高.氯代二氮杂萘联苯型聚醚酮的合成及性能[J].应用化学, 1999, 16(3): 106-108
[37]张守海,杨大令,蹇锡高.含磺酸钠基的杂萘联苯聚芳醚砜酮的合成与表征[J].高等学校化学学报, 2002, 12: 2382-2385
[38]蹇锡高,陈连周.新型杂环氯代聚芳醚酮的合成与性能[J].材料研究学报, 2001, 5: 500-504
[39]Takeuchi H, Kakimoto M, Imai Y. New synthetic method for aromatic polyketones from bis(arylsilane)s and aromatic dicarboxylic acid chloride. J. Polym. Sci., Part A: Polym. Chem, 2002, 40(16): 2729-2735
[40]Takeuchi H, Kakimoto M, Imai Y. New regioselective synthesis of metalinked aromatic polyketones from metasubstituted bis(arylsilane)s and aromatic dicarboxylic acid chlorides. J. Polym. Sci., Part A: Polym. Chem., 2003, 41(10): 1428-1434
[41]Baek J B, Tan L S. Improved synthesis of poly(oxy-1,3-phenylenecarbonyl-1,4- phenylene) and related poly(ether-ketone) using polyphosphoric acid/P2O5 as polymerization medium. Polymer, 2003, 44(15): 4135-4147
[42]Baek J B, Tan L S. Surface functionaliazation of vapor-grown carbon nanotube and in-situ polymerization of 3-phenoxybenzoic acid with vapor-grown carbon nanotube. Polym. Prepr., 2002, 43(1): 533-540
[43]Baek J B, Park S Y, Price G E, et al. Unusual thermal relaxation of viscosity-and-shear-induced strain in poly(ether-ketones) synthesized in highly viscous polyphosphoric acid/P2O5 medium. Polymer, 2005, 46(5): 1543-1552
[44]Matsumura S, Kihara N, Takata T. Properties of a few aromatic poly(thioether ketones) as sulfur-containing high-performance polymers. J. Appl. Poly. Sci., 2004, 92(3): 1869-1874
[45]Clendinning R A, Kelsey D R, Botkin J H, Winslow P A, Youssefi M, Cotter R J, Matzner M, Kwiatkowski G T. Poly(aryl ether ketone) block and chain-extended copolymers. 1. Preparation and characterization of a new class of functional poly(aryl ether ketone) oligomers. Macromolecules, 1993, 26(9): 2361-2365
[46]Carlier V, Pavanx J. About the synthesis of a high-temperature, crystalline poly [aryl ether(ketone-co-sulfone)]. 1. Synthetic reactions study. Polymer, 1994,35(2): 415-422
[47]Mazznnti J B. EP, 298770. 1989
[48]Tokai M. JP, 01121236
[49]Dahl K J. WO, 8602368. 1986
[50]Ritter H, Thonvirth R. Comb-like poly(aryl-ether-ketones) cotaining naphthalene moieties in the main chain. Makromol. Chem., 1993, 194(5): 1469-1481
[51]Ohno M, Takata T, Endo T. Synthesis of a novel naphthalene-based poly(arylene ether ketone) with high solubility and thermal stability. Macromolecules, 1994, 27(12): 3447-3448
[52]Niume K, Toda F, Uno K, et al. Syntheses of polyketones containing tricyclic fused rings and conversion to the polyamides in polyphosphor. J. polym. Sci. Polym. chem. Ed., 1982, 20: 1965-1970
[53]宣英男,黄勇,蹇锡高.环氧端基聚芳醚酮/环氧树脂复合体系的研究[J].高分子材料科学与工程, 2002, 18(2): 134-137
[54]盛寿日,罗秋燕,霍毅.几种甲基取代的新型可溶性聚芳醚酮醚砜醚酮的合成与表征.高分子材料科学与工程[J], 2006, 22(3): 85-87, 92
[55]高自宏,范星河.新型含硅聚芳醚酮的合成与表征[J].高等学校化学学报, 2005, 8: 1579-1581
[56]Hay A S. Polymers derived from phenolphthaleins. USP, 5254663. 1993- 10-19
[57]Jian X G, Cheng L. Synthesis of all-aromatic polyamides containing the1,2- dihydro-4-phenyl(2H)phtha-lazone moiety. J. Polym. Sci. Part A, Polym. Chem., 1999, 3: 1565-1567
[58]Liao G X, Jian X G, Guo X Y, et a1. Synthesis and properties of polyetherketones containing sulfide and phthalazinone. Chin. Chem. Lett., 2002, 13(7): 607-608
[59]童身毅,张潇.耐高温杂环聚芳醚酮的合成与表征[J].塑料工业, 2002, 30(3): 24-26
[60]王国庆,朱秀玲,张守海.一种杂环磺化聚芳醚腈酮质子交换膜材料的合成及表征[J].高分子学报, 2006, 2: 209-212
[61]王贵宾,陈春海,周宏伟.含氟侧基聚芳醚酮的合成与表征[J].高等学校化学学报, 2000, 21(8): 1325-1327
[62]刘伯军,陈春海,呼微.新型含氟聚芳醚酮的合成与表征[J].高等学校化学学报, 2002, 23(2): 321-323
[63]刘佰军,佰春海,金宇辉.新型可溶性聚芳醚酮的合成与表征[J].高等学校化学学报, 2002, 23(2): 324-326
[64]Lee J, Marvel C S. Polyaromatic ether-ketone sulfonamides prepared from polydiphenyl ether-ketones by chlorosulfonation and treatment with secondary amines. J. Polym. Sci. Polym. Chem. Ed., 1984, 22(2): 295-301
[65]Wang F, Roovers J. Functionalization of poly(aryl ether ether ketone) (PEEK): synthesis and properties of aldehyde and carboxylic acid substituted PEEK. Macromolecules, 1993, 26: 5295~5320
[66]Mohanty D K, Lin T S, Ward T C, et al. Novel synthesis of thermoplastic semicrystalline poly (arylene ether ketone). Materials Science for the Future: 31st International SAMPE Symposium and Exhibition. USA: California, 1986, 945-955
[67]盛寿日,周丽云,瞿志荣.含氯取代基的聚芳醚酮酮的合成与表征[J].石油化工, 1999, 28(5): 304-306
[68]盛寿日,康宜强,罗秋燕等.新型多氯取代聚芳醚酮的合成与表征[J].应用化学, 22(4): 387-390
[69]Bennett G S, Farris R J, Thompson S A. Amine-terminated poly(aryl ether ketone)-epoxy/amine resin systems as tough high performance materials. Polymer, 1991, 32(9): 1633-1641
[70]Yonezawa N, Mori S I, Miyata S, et al. Synthesis of aromatic poly(ether ketone)s having adhesion property to steel surface. React. Func. Polym., 2002, 53(1): 11-17
[71]郭庆中,王红华,景凤英. 13C NMR方法研究酚酞聚芳醚酮砜共聚物的序列结构[J].高分子学报, 2003, 2: 283-287
[72]张云鹤,王冬,朱亚明.新型含萘含氟聚芳醚酮的合成与表征[J].高等学校化学学报, 2005, 26(7): 1378-1380
[73]王洋,牟建新,祝存生.新型低介电常数聚芳醚酮的合成及性能研究[J].高等学校化学学报, 2005, 26(3): 586-588
[74]周宏伟,高自宏,刘新才.含硫醚可溶性聚芳醚酮的合成及电子束辐照的研究[J].高等学校化学学报, 2005, 26(6): 1180-1182
[75]James H C, James E D. Trifluoromethylated poly(ether ether ketone)s. Polymer, 1994, 35(23): 5124-5129
[76]Mercer F W, Fone M M, Reddy U N. Synthesis and characterizati0n of fluorinated polyetherketones prepared from decafluorobenzephenone. Polymer, 1997, 38(8): 1989-1995
[77]王贵宾,王东,姜振华.含氟聚芳醚酮的合成与性能研究[J].高等学校化学学报, 2001, 22(7): 1053-1056
[78]吴忠文等.特种工程塑料聚醚砜、聚醚醚酮树脂国内外研究、开发、生产现状[J].化工新型材料, 2002, 30(6): 15-18
[79]Zhang Y H, Sun X B, Xu R, et al. Synthesis and characterization of novel fluorine-containing poly(aryl ether ketone)s containing 1,4-naphthylene units. Mater. Chem. Phys., 2006, 2: 3465-3469
[80]Jikei M, Kakimoto M. Hyperbranched polymers:a promising new class of materials. Prog. Polym. Sci., 2001, 26(8): 1233-1285
[81]Gao C, Yan D. Hyperbranched polymers: from synthesis to applications. Prog. Polym. Sci., 2004, 29(3): 183-275
[82]Hawker C J, Chu F K. Hyperbranched Poly (ether ketones): Manipulation of structure and physical properties. Macromolecules, 1996, 29(12): 4370-4380
[83]Shu C F, Leu C. Hyperbranched poly (ether ketone) with carboxylic acid terminal groups: synthesis, characterization, and derivatization. Macromolecules, 1999, 32(1): 100-105
[84]Song Y C, Chang Y, Kim J S, et al. Hyperbranched poly(ether ketone) analogues with heterocyclic triazine moiety: synthesis and peripheral functionalization. Macromol. Chem. Phys., 2001, 202: 263-269
[85]牟建新,陈杰,张春玲等. B3型单体及超支化聚醚醚酮的合成与表征[J].吉林大学学报(理学版), 2005, 43(5): 662-665
[86]Baek J B, Tan L S. Hyperbranched poly(phenylquinoxaline-ether-ketone) synthesis in poly (phosphoric acid)/P2O5 Medium: optimization and some interesting observations. Macromolecules, 2006, 39(8): 2794-2803
[87]Wang D H, Baek J B, Tan L S. Grafting of vapor-grown carbon nanofibers (VGCNF) with a hyperbranched poly(ether-ketone). Mate. Sci. Eng., 2006, 132(12): 103-107
[88]Lee H J, Lee E M, Lee M H, et al. Crosslinkable fluorinated poly(arylene ethers) bearing phenyl ethynyl moiety for low-loss polymer optical waveguide devices. J. Polym. Sci., Part A: Polym. Chem., 1998, 36: 2881-2887
[89]Kim J P, Lee W Y, Wook K, et al. Fluorinated poly (arylene ether sulfide) for polymeric optical waveguide devices. Macromolecules, 2001, 34(22): 7817-7821
[90]Lee H J, Lee M H, Oh M C, et al. Crosslinkable polymers for optical waveguide devices. II. Fluorinated ether ketone oligomers bearing ethynyl group at the chain end. J. Polym. Sci., Part A: Polym. Chem., 1999, 37: 2355-2361
[91]Tan B, Vasudevan V, Lee Y J, et al. Design and characterization of thermosetting polyimide structural adhesive and composite matrix systems. J. Polym. Sci., PartA: Polym. Chem., 1997, 35: 2943-2945
[92]秦明,益小苏.可控交联聚芳醚酮改性电子束固化环氧树脂结构与性能研究[J].材料工程, 2003, 11: 28-31
[93]吴雪梅,贺高红,顾爽.胺交联的磺化聚芳醚砜酮荷电膜的制备及微观结构[J].功能材料, 2006, 37(8): 1341-1344.
[94]Ma X Y, Liu B J, Wang D, et al. Synthesis and characterization of fluorinated poly(aryl ether ether ketone)s terminated with a phenylethynyl group. Materials Letters, 2006, 60(11): 1369-1373
[95]刘佰军,呼微,马晓野等.可交联含氟聚醚醚酮的合成[J].高等学校化学学报. 2003, 24(7): 1329-1331
[96]Hunter R A, Turner P D, Rimmer S. Suspension cross-linking of poly(aryl ether ketone)s containing carboxylic acid functionality. J. Mater. Chem., 2001, 11: 736-740
[97]Yingnan X, Yan G, Yong H, et al. Synthesis and characterization of a novel phthala-zinone poly (aryl ether sulfone ketone) with carboxyl group. J. Appl. Polym. Sci., 2003, 88: 1111-1114
[98]Zhang Y H, Sun X B, Xu R, et al. Synthesis and characterization of novel fluorine-containing poly(aryl ether ketone)s containing 1,4-naphthylene units. Mater. Chem. Phys., 2006, 2: 3465-3469
[99]Harris J E, Winslow P A, Bottin J H. Poly(aryl ether ketone) (PAEK) block and chain-extended copolymers.2.Preparation and characterization of chain-extended PAEK copolymers and poly(ether ketone ketone)/poly(ether ether ketone) block copolymers. Macromolecules, 1993, 26(9): 2366-2371
[100]Botkin J H, Cotter R J, Matzner M, et al. Poly(aryl ether ketone) block and chain-extended copolymers.3. Preparation and characterization of poly(ether ketone ketone)/poly(ether sulfone) block copolymers. Macromolecules, 1993, 26(9): 2372-2376
[101]Harris J E, Robeson L M. USP, 4609714(to Union Carbide Corp.). 1986
[102]Harris J E, Robeson L M. Miscible blends of poly(aryl ether ketone)s and polyetherimides. J. Appl. Polym. Sci., 1988, 35: 1877-1891
[103]何伟,廖功雄,曲敏杰. PPESK/PTFE共混物摩擦行为研究[J].中国塑料, 2006, 20(2): 34-37
[104]Stuart B H, Briscoe B J. Scratch hardness studies of PEEK. Polymer, 1996, 37(17): 3819-3824
[105]Hanchi J, Eiss N S. Synergistic friction and wear of ternary blends of PEEK,PEI and a TLCP at elevated temperatures. Tribology Trans, 1997, 40(1): 102-110
[106]Malik T M. Thermal and mechanical characterization of partially miscible blends of poly(ether ether ketone) and polyethersulfone. J. Appl. polym. Sci., Part B: Polym. phys., 1992, 46: 303-110
[107]来育梅,程茹,黄培. PEEK/PEI共混物的相容性和结晶行为研究[J].塑料工业. 2006, 34(6): 40-45
[108]麦堪成,许家瑞,梅震等.结晶/结晶共混体系聚苯硫酸/聚醚醚酮中聚醚醚酮组分的结晶熔融行为─熔融温度的影响[J].高分子学报, 1994, 5: 631-635
[109]Chen D H, Chen Y P, Arnold C A, Hedrick J C, Graybeal J D, McGrath J E. SAMPE Int. symp., 1989, 34: 1247
[110]Musto P, Karasz F E, Macknight W J. Hydrogen bondin in polybenzi-midazole /polyimide systems: a fourier-transform infra-redinvestigation using low-molecular-weight monofunctional probes. Polymer, 1989, 30(6): 1012-1021
[111]Guerra G, Choe S, Williams D J, Karaze F E, Macknight W J. Fourier transform infrared spectroscopy of some miscible polybenzimidazole/polyimide blends. Macromolecules, 1988, 21: 231-234
[112]白杉,周洁.聚醚醚酮树脂应用现状[J].化工科技市场, 2004, 27(8): 21-23, 13
[113]Kuo M C, Huang J C, Chen M. Non-isothermal crystallization kinetic behavior of alumina nanoparticle filled poly (ether ether ketone). Mater. Chem. Phys., 2006, 99(2-3): 258-268
[114]He W, Liao G X, Jian X G, et al. Dynamic mechanical thermal behaviour of novel poly(phthalazinone ether sulfone ketone)and poly(tetraflu-oroethylene) blends. J. Polym. Eng., 2006, 26(6): 617-631
[115]那辉,苑晶,倪宏伟.含联苯结构聚醚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
[116]盛寿日,蔡明中,宋才生.聚醚酮酮/含萘环聚醚砜醚酮酮无规共聚物的合成与性能[J].高分子学报, 1998, 5: 616-619
[117]孟跃中,张世振,张宏书.嵌段半结晶聚芳醚酮及其合成方法[D].中国专利, 01107474. 2001-07-25
[118]Francis B, Rao V L, Jose S, et al. Poly(ether ether ketone) with pendent methyl groups as a toughening agent for amine cured DGEBA epoxy resin. J. Mater. Sci., 2006, 41(17): 5467-5479
[119]Francis B,Thomas S, Jose J, et al. Hydroxyl terminated poly (ether ether ketone) with pendent methyl group toughened epoxy resin: miscibility, morphology andmechanical properties. Polymer, 2005, 46(26): 12372-12385
[120]Francis B, Ramaswamy R, Rao V L, et al. Toughening of diglycidyl ether of bisphenol-a epoxy resin using poly (ether ether ketone) with pendent ditert- butyl groups. International Journal of Polymeric Materials, 2006, 55(9): 681-702
[121]Francis B, Rao V L, Poel G V, et al. Cure kinetics,morphological and dynamic mechanical analysis of diglycidyl ether of bisphenol-A epoxy resin modified with hydroxyl terminated poly(ether ether ketone) containing pendent tertiary butylgroups. Polymer, 2006, 47(15): 5411-5419
[122]Francis B, Thomas S, Asari G V, et al. Synthesis of hydroxyl-terminated poly (ether ether ketone) with pendent tert-butyl groups and its use as a toughener for epoxy resins. J. Polym. Sci., Part B: Polym. Phys., 2006, 44: 541-556
[123]周其凤,范星河,谢晓峰.耐高温聚合物及其复合材料—合成、应用与进展[M].北京:化学工业出版社, 2004. 113-138
[124]Lakshmana, Rao V J. Macromol. Sci. Rev. Macromol. Chem. Phys., 1995, 35(4): 661-712
[125]Kh G, Thomas S, Yang Z G, et al. Failure behavior and performance analysis of hybrid-fiber reinforced PAEK composites at high temperature. Composites Science and Technology, 1997, 58(9): 1509-1518
[126]Gan D J, Lu S Q, Song C S, et al. Physical properties of poly(aryl ether ketone)/mica composites: effect of filler content. Materials Letters, 2001, 48(5): 299-302
[127]Gan D J, Lu S Q, Song C S, et al. Mechanical properties and frictional behavior of a mica-filled poly(aryl ether ketone) composite. Polymer, 2001, 37(7): 1359-1365
[128]齐颖华,陈天禄,刘盛洲等.聚硫醚醚酮(砜)芳香环状低聚物的合成与自由基开环聚合[J].高等学校化学学报, 2000, 21: 480-483
[129]谌烈,宋才生,童永芬,温红丽,刘晓玲. 2,2',6,6'-四甲基-4,4'-二苯氧基二苯砜的合成与表征[J].江西师范大学学报(自然科学版), 2003, 28(1): 83-85
[130]Zolotukhin M G, Rueda D R, Balta Calleja F J, Cagiao M E, Bruix M, Sedova E A, Gileva N G. Aromatic polymers obtained by precipitation polyconden-sation: 4*. Synthesis of poly(ether ketone ketone). Polymer, 1997, 38: 1471-1476
[131]戴润英,宋才生,钟鸣,徐玲,黄红. 1,4-二(4-苯氧基苯甲酰基)苯的合成与表征[J].江西师范大学学报(自然科学版), 2007, 31(5): 518-522
[132]唐旭东,王艳,贺征华等.特种工程塑料聚芳醚酮的研究进展[J].天津科技44大学学报, 2006, 21(1): 29-32
[133]钟鸣,宋才生,童永芬等.含间苯基及甲基侧基聚芳醚砜醚酮酮的合成与表征[J].江西师范大学学报(自然科学版), 2005, 29(3): 193-195
[134]付长清,宋才生,刘勇军等.聚芳醚酮酮、聚芳醚醚酮酮无规共聚物的合成与性能研究[J].江西师范大学学报(自然科学版), 2005, 29(5): 377-380
[135]WEN Hong-li, SONG Cai-sheng, TONG Yong-fen, et al. Synthesis and properties of poly(aryl ether sulfene ether ketone ketone)(PESEKK). Journal of Applied Polymer Science, 2005, 96: 489-493
[136]Kelkar A J, Paul D R. Water vapor transport in a series of polyarylate. Journal of Membrane Science, 2001, 181: 199-212
[137]徐玲,宋才生,黄红等.高摩尔质量双酚A型聚芳酯的合成工艺研究[J].塑料工业, 2008, 36(4): 13-16
[138]汪薇,郭晓晖,林保平.双酚A型聚芳酯的相转移催化合成[J].化工时刊, 2004, 18(5): 35-41
[139]Harry R A, Frederick W L, Janes E M. Contemporary polymer chemistry.北京:化学工业出版社, 2006. 25-27
[140]王祖明,袁宝庆.芳香族聚酰胺纤维生产技术与应用[J].化工新型材料, 2004, 32(11): 1-5
[141]何伟,李振中,张文燕.聚酰胺复合材料增强增韧研究进展[J].中国塑料, 2006, 20(3): 1-6
[142]金国珍.工程塑料[M].北京:化学工业出版社, 2001. 420-425
[143]崔永丽,应鹏晨,王晓红.特种工程塑料聚芳醚酮[J].塑料工业, 2006, 34: 295-298
[144]谌烈,宋才生,童永芬,温红丽,刘晓玲.双邻位甲基取代的聚芳醚酮合成与表征[J].高分子学报, 2005, 1: 119-123
[145]莫志深,张宏放.晶态聚合物结构和X射线衍射[M].北京:科学出版社, 2003. 58-67
[146]Daniel R R, Mikhail G Z. Cold crystallization and polymorphismin an oligo(aryl ether ketone). Macromol. Chem. Phy., 1997, 198: 3517-3528
[147]Benjamin S H, Kenncorwin H, et al. Crystallization of poly(aryl ether ketone ketone) copolymers containing terephthalate/isophthalate moieties. Journal of Polymer Science, 1994, 32: 2585-2594
[148]Tianxi Liu, Zhishen Mo, Shanger Wang, Hongfang Zhang, Hui Na, Zhongwen Wu. Macromol. Rapid Commun, 1997, 18: 23-30
[149]柯扬船,吴忠文,郑玉斌.含间位取代苯基聚醚酮酮的结晶与晶体结构研究[J].高分子学报, 1997, 2: 177-182
[150]柯扬船,朱志宁,牟忠诚,吴忠文.聚醚酮酮及其低聚物晶体的多晶型结构[J].材料研究学报, 1997, 11(5): 491-495
[151]柯扬船,郑玉斌,王军佐,吴忠文.聚醚酮酮第Ⅱ晶型结构的WAXD研究[J].高分子材料科学与工程, 1997, 13(5): 85-90
[152]邱兆斌,莫志深,张宏放,盛寿日,宋才生.含间位聚醚酮醚酮酮的合成与结晶[J].应用化学, 1999, 16(5): 109-110
[153]苏爱华,汪爱莲.全对位聚芳醚酮酮的结晶行为[J].上饶师专学报, 1999, 19(3): 49-53
[154]Blundel D J, Newton A B. Variations in the crystal lattice of PEEK and related para-substituted aromatic polymers.Ⅱeffect of sequence and proportion of ether and ketone links. Polymer, 1991, 32: 308-313
[155]Gardner K H, Hsiao B S, Matheson R R. Structure, crystallization and morphology of poly(aryl ether ketone ketone). Polymer, 1992, 33: 2484-2495
[156]Ho Rongming, Cheng Stephen Z D, Hsiao B S. Crystal morphology and phase identifications in poly(aryl ether ketone)s and their copolymers. 1. Polymorphism in PEKK. Macromolecules, 1994, 27(8): 2136-2140
[157]Ho Rongming, Cheng Stephen Z D, Fisher H P. Crystal morphology and phase identifications in poly(aryl ether ketone)s and their copolymers. 2. Poly(oxy-1,4-phenylenecarbonyl-1,3-phenylenecarbonyl-1,4-phenylenene). Macromolecules, 1994, 27(20): 5787-5793
[158]Gadner K H, Hsiao B S, Faron Katherine L. Polymorphism in poly(aryl ether ketone)s. Polymer, 1994, 35: 2290-2295
[2]Olah G A, et al. Friedel-Crafts and Related Reactions. John Wiley and Sons Ltd London, 1964, 3: 1014-1020
[3]Charles E B. USP, 3516966. 1970
[4]Chang Ike Y. SAMPE Quarterly, 1988, 19(4): 29-34
[5]曹俊奎,苏文成,吴忠文.刚性链嵌段共聚物的研究(Ⅱ) -含双酚S的聚醚醚酮共聚物合成与性能[J].高分子学报, 1994, 4: 477-481
[6]曹俊奎等.聚醚醚酮/聚醚砜嵌段共聚物的动态力学行为[J].高等学校化学学报, 1994, 14(5): 738-740
[7]曹俊奎,黄智华,吴忠文.聚醚醚酮分子结构对流动性和热性能的影响[J].高分子学报, 1994, 1: 27-29
[8]曹俊奎等.刚性链嵌段共聚物的研究(Ⅲ) -PEEK/HTA有规嵌段共聚物的合成与性能[J].高等学校化学学报, 1994, 15(1): 145-149
[9]曹俊奎等.刚性链嵌段共聚物的研究(Ⅳ)-聚醚醚酮/苯酞圈型聚芳醚砜有规嵌段共聚物的合成与部分性能[J].高等学校化学学报, 1994, 15(2): 303-307
[10]张万金,吴忠文等.高性能聚芳醚酮的合成与性能(Ⅰ) -对苯二酚、联苯二酚、4,4'-二氟二苯酮三元共聚体系[J].高等学校化学学, 1993, 14(5): 738-740
[11]郭纯孝,张万金,牛力,蒋大振,黄东律.含二联苯结构聚醚醚酮的微结构及磺化改性的性质研究[J].高等学校化学学报, 1994, 15(2): 240-243
[12]张万金,吴忠文等.一种含联苯的聚醚醚酮酮的合成与表征[J].应用化学, 1993, 10(6): 106-108
[13]王军佐.聚芳醚酮类高聚物的合成与热性能研究[J].高等学校化学学报, 1993, 14(9): 1308-1311
[14]苑晶,张万金,那辉等.联苯聚醚醚酮酮的合成与性能研究[J].高等学校化学学报, 1994, 15(5): 763-766
[15]张海春,陈天禄.一步法合成带有酞侧基的聚芳醚砜[P].中国专利, 85108751. 1985
[16]李滨耀,庄国庆.酞侧基聚芳醚砜和聚芳醚酮共混物的高温流变行为[J].高分子学报, 1994, 3: 289-291
[17]蹇锡高, Hay AS,郑海滨.含二氮杂萘酮结构的聚醚砜及制备法[P].中国专利, CN93109180.2. 1993-07-26
[18]孟跃中,蹇锡高,郑海滨等.杂环取代联苯型聚醚酮的合成与表征[J].高分子材料科学与工程, 1994, 10(2): 22-25
[19]孟跃中,蹇锡高等.杂环联苯型聚芳醚酮热稳定性研究[J].高分子材料科学与工程, 1994, 10(6): 85-88
[20]宋才生等.亲电聚合路线合成聚芳醚酮砜的研究[J].高分子材料, 1993, 3: 2-5
[21]蔡明中等.亲电聚合路线合成聚醚醚酮酮砜的研究[J].精细石油化工, 1993, 950: 15-18
[22]蔡明中,宋才生,周丽云.亲电聚合路线合成含氯取代基的聚芳醚酮酮的研究[J].化学世界, 1993, 10: 486-488
[23]宋才生等.低温溶液缩聚合成聚芳醚酮酮的研究[J].高分子学报, 1995, 1: 99-102
[24]盛寿日,蔡明中,宋才生.含间苯基聚醚酮醚酮酮的合成和性能研究[J].高分子学报, 1999, 4: 490-493
[25]黎苇,蔡明中,宋才生. 4,4'-二苯氧基二苯砜、4,4'-二苯氧基二苯酮、对苯二甲酰氯三元共聚物的合成[J].应用化学, 2002, 7: 653-656
[26]谌烈.含双邻位甲基聚芳醚砜和聚芳醚酮的合成与性能研究[D]: [硕士学位论文].江西:江西师范大学化学化工学院, 2004
[27]童永芬.聚芳醚砜以及聚芳醚酮的合成与性能研究[D]: [硕士学位论文].江西:江西师范大学化学化工学院, 2004
[28]钟鸣.聚芳醚酮和聚芳醚砜的合成与改性研究[D]: [硕士学位论文].江西:江西师范大学化学化工学院, 2006
[29]吴方娟.聚芳醚砜亚胺酮的合成与表征[D]: [硕士学位论文].江西:江西师范大学化学化工学院, 2007
[30]戴润英.聚芳醚酮嵌段共聚合成及其结构与性能研究[D]: [硕士学位论文].江西:江西师范大学化学化工学院, 2008
[31]黄红.新型耐高温聚芳醚酮及其单体的合成与性能研究[D]: [硕士学位论文].江西:江西师范大学化学化工学院, 2008
[32]Hoffmann U, Klapper M, Mül K. Phase-transfer catalyzed synthesis of poly(etherketone)s. Polymer Bulletin, 2004, 30(5): 481-488
[33]刘彦军,蹇锡高,刘圣军.含二氮杂萘酮结构聚醚酮的合成与表征[J].高分子学报, 1999, 1: 37-41
[34]高燕,蹇锡高.含二氮杂萘酮和萘结构聚芳醚酮的研究[J].高分子材料科学与工程, 2001, 17(3): 160-162
[35]李秀华,孟跃中,蹇锡高.含二氮杂萘酮结构的新型共聚醚酮的合成及性能[J].高分子材料科学与工程, 1998, 14(4): 37-39
[36]陈连周,蹇锡高.氯代二氮杂萘联苯型聚醚酮的合成及性能[J].应用化学, 1999, 16(3): 106-108
[37]张守海,杨大令,蹇锡高.含磺酸钠基的杂萘联苯聚芳醚砜酮的合成与表征[J].高等学校化学学报, 2002, 12: 2382-2385
[38]蹇锡高,陈连周.新型杂环氯代聚芳醚酮的合成与性能[J].材料研究学报, 2001, 5: 500-504
[39]Takeuchi H, Kakimoto M, Imai Y. New synthetic method for aromatic polyketones from bis(arylsilane)s and aromatic dicarboxylic acid chloride. J. Polym. Sci., Part A: Polym. Chem, 2002, 40(16): 2729-2735
[40]Takeuchi H, Kakimoto M, Imai Y. New regioselective synthesis of metalinked aromatic polyketones from metasubstituted bis(arylsilane)s and aromatic dicarboxylic acid chlorides. J. Polym. Sci., Part A: Polym. Chem., 2003, 41(10): 1428-1434
[41]Baek J B, Tan L S. Improved synthesis of poly(oxy-1,3-phenylenecarbonyl-1,4- phenylene) and related poly(ether-ketone) using polyphosphoric acid/P2O5 as polymerization medium. Polymer, 2003, 44(15): 4135-4147
[42]Baek J B, Tan L S. Surface functionaliazation of vapor-grown carbon nanotube and in-situ polymerization of 3-phenoxybenzoic acid with vapor-grown carbon nanotube. Polym. Prepr., 2002, 43(1): 533-540
[43]Baek J B, Park S Y, Price G E, et al. Unusual thermal relaxation of viscosity-and-shear-induced strain in poly(ether-ketones) synthesized in highly viscous polyphosphoric acid/P2O5 medium. Polymer, 2005, 46(5): 1543-1552
[44]Matsumura S, Kihara N, Takata T. Properties of a few aromatic poly(thioether ketones) as sulfur-containing high-performance polymers. J. Appl. Poly. Sci., 2004, 92(3): 1869-1874
[45]Clendinning R A, Kelsey D R, Botkin J H, Winslow P A, Youssefi M, Cotter R J, Matzner M, Kwiatkowski G T. Poly(aryl ether ketone) block and chain-extended copolymers. 1. Preparation and characterization of a new class of functional poly(aryl ether ketone) oligomers. Macromolecules, 1993, 26(9): 2361-2365
[46]Carlier V, Pavanx J. About the synthesis of a high-temperature, crystalline poly [aryl ether(ketone-co-sulfone)]. 1. Synthetic reactions study. Polymer, 1994,35(2): 415-422
[47]Mazznnti J B. EP, 298770. 1989
[48]Tokai M. JP, 01121236
[49]Dahl K J. WO, 8602368. 1986
[50]Ritter H, Thonvirth R. Comb-like poly(aryl-ether-ketones) cotaining naphthalene moieties in the main chain. Makromol. Chem., 1993, 194(5): 1469-1481
[51]Ohno M, Takata T, Endo T. Synthesis of a novel naphthalene-based poly(arylene ether ketone) with high solubility and thermal stability. Macromolecules, 1994, 27(12): 3447-3448
[52]Niume K, Toda F, Uno K, et al. Syntheses of polyketones containing tricyclic fused rings and conversion to the polyamides in polyphosphor. J. polym. Sci. Polym. chem. Ed., 1982, 20: 1965-1970
[53]宣英男,黄勇,蹇锡高.环氧端基聚芳醚酮/环氧树脂复合体系的研究[J].高分子材料科学与工程, 2002, 18(2): 134-137
[54]盛寿日,罗秋燕,霍毅.几种甲基取代的新型可溶性聚芳醚酮醚砜醚酮的合成与表征.高分子材料科学与工程[J], 2006, 22(3): 85-87, 92
[55]高自宏,范星河.新型含硅聚芳醚酮的合成与表征[J].高等学校化学学报, 2005, 8: 1579-1581
[56]Hay A S. Polymers derived from phenolphthaleins. USP, 5254663. 1993- 10-19
[57]Jian X G, Cheng L. Synthesis of all-aromatic polyamides containing the1,2- dihydro-4-phenyl(2H)phtha-lazone moiety. J. Polym. Sci. Part A, Polym. Chem., 1999, 3: 1565-1567
[58]Liao G X, Jian X G, Guo X Y, et a1. Synthesis and properties of polyetherketones containing sulfide and phthalazinone. Chin. Chem. Lett., 2002, 13(7): 607-608
[59]童身毅,张潇.耐高温杂环聚芳醚酮的合成与表征[J].塑料工业, 2002, 30(3): 24-26
[60]王国庆,朱秀玲,张守海.一种杂环磺化聚芳醚腈酮质子交换膜材料的合成及表征[J].高分子学报, 2006, 2: 209-212
[61]王贵宾,陈春海,周宏伟.含氟侧基聚芳醚酮的合成与表征[J].高等学校化学学报, 2000, 21(8): 1325-1327
[62]刘伯军,陈春海,呼微.新型含氟聚芳醚酮的合成与表征[J].高等学校化学学报, 2002, 23(2): 321-323
[63]刘佰军,佰春海,金宇辉.新型可溶性聚芳醚酮的合成与表征[J].高等学校化学学报, 2002, 23(2): 324-326
[64]Lee J, Marvel C S. Polyaromatic ether-ketone sulfonamides prepared from polydiphenyl ether-ketones by chlorosulfonation and treatment with secondary amines. J. Polym. Sci. Polym. Chem. Ed., 1984, 22(2): 295-301
[65]Wang F, Roovers J. Functionalization of poly(aryl ether ether ketone) (PEEK): synthesis and properties of aldehyde and carboxylic acid substituted PEEK. Macromolecules, 1993, 26: 5295~5320
[66]Mohanty D K, Lin T S, Ward T C, et al. Novel synthesis of thermoplastic semicrystalline poly (arylene ether ketone). Materials Science for the Future: 31st International SAMPE Symposium and Exhibition. USA: California, 1986, 945-955
[67]盛寿日,周丽云,瞿志荣.含氯取代基的聚芳醚酮酮的合成与表征[J].石油化工, 1999, 28(5): 304-306
[68]盛寿日,康宜强,罗秋燕等.新型多氯取代聚芳醚酮的合成与表征[J].应用化学, 22(4): 387-390
[69]Bennett G S, Farris R J, Thompson S A. Amine-terminated poly(aryl ether ketone)-epoxy/amine resin systems as tough high performance materials. Polymer, 1991, 32(9): 1633-1641
[70]Yonezawa N, Mori S I, Miyata S, et al. Synthesis of aromatic poly(ether ketone)s having adhesion property to steel surface. React. Func. Polym., 2002, 53(1): 11-17
[71]郭庆中,王红华,景凤英. 13C NMR方法研究酚酞聚芳醚酮砜共聚物的序列结构[J].高分子学报, 2003, 2: 283-287
[72]张云鹤,王冬,朱亚明.新型含萘含氟聚芳醚酮的合成与表征[J].高等学校化学学报, 2005, 26(7): 1378-1380
[73]王洋,牟建新,祝存生.新型低介电常数聚芳醚酮的合成及性能研究[J].高等学校化学学报, 2005, 26(3): 586-588
[74]周宏伟,高自宏,刘新才.含硫醚可溶性聚芳醚酮的合成及电子束辐照的研究[J].高等学校化学学报, 2005, 26(6): 1180-1182
[75]James H C, James E D. Trifluoromethylated poly(ether ether ketone)s. Polymer, 1994, 35(23): 5124-5129
[76]Mercer F W, Fone M M, Reddy U N. Synthesis and characterizati0n of fluorinated polyetherketones prepared from decafluorobenzephenone. Polymer, 1997, 38(8): 1989-1995
[77]王贵宾,王东,姜振华.含氟聚芳醚酮的合成与性能研究[J].高等学校化学学报, 2001, 22(7): 1053-1056
[78]吴忠文等.特种工程塑料聚醚砜、聚醚醚酮树脂国内外研究、开发、生产现状[J].化工新型材料, 2002, 30(6): 15-18
[79]Zhang Y H, Sun X B, Xu R, et al. Synthesis and characterization of novel fluorine-containing poly(aryl ether ketone)s containing 1,4-naphthylene units. Mater. Chem. Phys., 2006, 2: 3465-3469
[80]Jikei M, Kakimoto M. Hyperbranched polymers:a promising new class of materials. Prog. Polym. Sci., 2001, 26(8): 1233-1285
[81]Gao C, Yan D. Hyperbranched polymers: from synthesis to applications. Prog. Polym. Sci., 2004, 29(3): 183-275
[82]Hawker C J, Chu F K. Hyperbranched Poly (ether ketones): Manipulation of structure and physical properties. Macromolecules, 1996, 29(12): 4370-4380
[83]Shu C F, Leu C. Hyperbranched poly (ether ketone) with carboxylic acid terminal groups: synthesis, characterization, and derivatization. Macromolecules, 1999, 32(1): 100-105
[84]Song Y C, Chang Y, Kim J S, et al. Hyperbranched poly(ether ketone) analogues with heterocyclic triazine moiety: synthesis and peripheral functionalization. Macromol. Chem. Phys., 2001, 202: 263-269
[85]牟建新,陈杰,张春玲等. B3型单体及超支化聚醚醚酮的合成与表征[J].吉林大学学报(理学版), 2005, 43(5): 662-665
[86]Baek J B, Tan L S. Hyperbranched poly(phenylquinoxaline-ether-ketone) synthesis in poly (phosphoric acid)/P2O5 Medium: optimization and some interesting observations. Macromolecules, 2006, 39(8): 2794-2803
[87]Wang D H, Baek J B, Tan L S. Grafting of vapor-grown carbon nanofibers (VGCNF) with a hyperbranched poly(ether-ketone). Mate. Sci. Eng., 2006, 132(12): 103-107
[88]Lee H J, Lee E M, Lee M H, et al. Crosslinkable fluorinated poly(arylene ethers) bearing phenyl ethynyl moiety for low-loss polymer optical waveguide devices. J. Polym. Sci., Part A: Polym. Chem., 1998, 36: 2881-2887
[89]Kim J P, Lee W Y, Wook K, et al. Fluorinated poly (arylene ether sulfide) for polymeric optical waveguide devices. Macromolecules, 2001, 34(22): 7817-7821
[90]Lee H J, Lee M H, Oh M C, et al. Crosslinkable polymers for optical waveguide devices. II. Fluorinated ether ketone oligomers bearing ethynyl group at the chain end. J. Polym. Sci., Part A: Polym. Chem., 1999, 37: 2355-2361
[91]Tan B, Vasudevan V, Lee Y J, et al. Design and characterization of thermosetting polyimide structural adhesive and composite matrix systems. J. Polym. Sci., PartA: Polym. Chem., 1997, 35: 2943-2945
[92]秦明,益小苏.可控交联聚芳醚酮改性电子束固化环氧树脂结构与性能研究[J].材料工程, 2003, 11: 28-31
[93]吴雪梅,贺高红,顾爽.胺交联的磺化聚芳醚砜酮荷电膜的制备及微观结构[J].功能材料, 2006, 37(8): 1341-1344.
[94]Ma X Y, Liu B J, Wang D, et al. Synthesis and characterization of fluorinated poly(aryl ether ether ketone)s terminated with a phenylethynyl group. Materials Letters, 2006, 60(11): 1369-1373
[95]刘佰军,呼微,马晓野等.可交联含氟聚醚醚酮的合成[J].高等学校化学学报. 2003, 24(7): 1329-1331
[96]Hunter R A, Turner P D, Rimmer S. Suspension cross-linking of poly(aryl ether ketone)s containing carboxylic acid functionality. J. Mater. Chem., 2001, 11: 736-740
[97]Yingnan X, Yan G, Yong H, et al. Synthesis and characterization of a novel phthala-zinone poly (aryl ether sulfone ketone) with carboxyl group. J. Appl. Polym. Sci., 2003, 88: 1111-1114
[98]Zhang Y H, Sun X B, Xu R, et al. Synthesis and characterization of novel fluorine-containing poly(aryl ether ketone)s containing 1,4-naphthylene units. Mater. Chem. Phys., 2006, 2: 3465-3469
[99]Harris J E, Winslow P A, Bottin J H. Poly(aryl ether ketone) (PAEK) block and chain-extended copolymers.2.Preparation and characterization of chain-extended PAEK copolymers and poly(ether ketone ketone)/poly(ether ether ketone) block copolymers. Macromolecules, 1993, 26(9): 2366-2371
[100]Botkin J H, Cotter R J, Matzner M, et al. Poly(aryl ether ketone) block and chain-extended copolymers.3. Preparation and characterization of poly(ether ketone ketone)/poly(ether sulfone) block copolymers. Macromolecules, 1993, 26(9): 2372-2376
[101]Harris J E, Robeson L M. USP, 4609714(to Union Carbide Corp.). 1986
[102]Harris J E, Robeson L M. Miscible blends of poly(aryl ether ketone)s and polyetherimides. J. Appl. Polym. Sci., 1988, 35: 1877-1891
[103]何伟,廖功雄,曲敏杰. PPESK/PTFE共混物摩擦行为研究[J].中国塑料, 2006, 20(2): 34-37
[104]Stuart B H, Briscoe B J. Scratch hardness studies of PEEK. Polymer, 1996, 37(17): 3819-3824
[105]Hanchi J, Eiss N S. Synergistic friction and wear of ternary blends of PEEK,PEI and a TLCP at elevated temperatures. Tribology Trans, 1997, 40(1): 102-110
[106]Malik T M. Thermal and mechanical characterization of partially miscible blends of poly(ether ether ketone) and polyethersulfone. J. Appl. polym. Sci., Part B: Polym. phys., 1992, 46: 303-110
[107]来育梅,程茹,黄培. PEEK/PEI共混物的相容性和结晶行为研究[J].塑料工业. 2006, 34(6): 40-45
[108]麦堪成,许家瑞,梅震等.结晶/结晶共混体系聚苯硫酸/聚醚醚酮中聚醚醚酮组分的结晶熔融行为─熔融温度的影响[J].高分子学报, 1994, 5: 631-635
[109]Chen D H, Chen Y P, Arnold C A, Hedrick J C, Graybeal J D, McGrath J E. SAMPE Int. symp., 1989, 34: 1247
[110]Musto P, Karasz F E, Macknight W J. Hydrogen bondin in polybenzi-midazole /polyimide systems: a fourier-transform infra-redinvestigation using low-molecular-weight monofunctional probes. Polymer, 1989, 30(6): 1012-1021
[111]Guerra G, Choe S, Williams D J, Karaze F E, Macknight W J. Fourier transform infrared spectroscopy of some miscible polybenzimidazole/polyimide blends. Macromolecules, 1988, 21: 231-234
[112]白杉,周洁.聚醚醚酮树脂应用现状[J].化工科技市场, 2004, 27(8): 21-23, 13
[113]Kuo M C, Huang J C, Chen M. Non-isothermal crystallization kinetic behavior of alumina nanoparticle filled poly (ether ether ketone). Mater. Chem. Phys., 2006, 99(2-3): 258-268
[114]He W, Liao G X, Jian X G, et al. Dynamic mechanical thermal behaviour of novel poly(phthalazinone ether sulfone ketone)and poly(tetraflu-oroethylene) blends. J. Polym. Eng., 2006, 26(6): 617-631
[115]那辉,苑晶,倪宏伟.含联苯结构聚醚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
[116]盛寿日,蔡明中,宋才生.聚醚酮酮/含萘环聚醚砜醚酮酮无规共聚物的合成与性能[J].高分子学报, 1998, 5: 616-619
[117]孟跃中,张世振,张宏书.嵌段半结晶聚芳醚酮及其合成方法[D].中国专利, 01107474. 2001-07-25
[118]Francis B, Rao V L, Jose S, et al. Poly(ether ether ketone) with pendent methyl groups as a toughening agent for amine cured DGEBA epoxy resin. J. Mater. Sci., 2006, 41(17): 5467-5479
[119]Francis B,Thomas S, Jose J, et al. Hydroxyl terminated poly (ether ether ketone) with pendent methyl group toughened epoxy resin: miscibility, morphology andmechanical properties. Polymer, 2005, 46(26): 12372-12385
[120]Francis B, Ramaswamy R, Rao V L, et al. Toughening of diglycidyl ether of bisphenol-a epoxy resin using poly (ether ether ketone) with pendent ditert- butyl groups. International Journal of Polymeric Materials, 2006, 55(9): 681-702
[121]Francis B, Rao V L, Poel G V, et al. Cure kinetics,morphological and dynamic mechanical analysis of diglycidyl ether of bisphenol-A epoxy resin modified with hydroxyl terminated poly(ether ether ketone) containing pendent tertiary butylgroups. Polymer, 2006, 47(15): 5411-5419
[122]Francis B, Thomas S, Asari G V, et al. Synthesis of hydroxyl-terminated poly (ether ether ketone) with pendent tert-butyl groups and its use as a toughener for epoxy resins. J. Polym. Sci., Part B: Polym. Phys., 2006, 44: 541-556
[123]周其凤,范星河,谢晓峰.耐高温聚合物及其复合材料—合成、应用与进展[M].北京:化学工业出版社, 2004. 113-138
[124]Lakshmana, Rao V J. Macromol. Sci. Rev. Macromol. Chem. Phys., 1995, 35(4): 661-712
[125]Kh G, Thomas S, Yang Z G, et al. Failure behavior and performance analysis of hybrid-fiber reinforced PAEK composites at high temperature. Composites Science and Technology, 1997, 58(9): 1509-1518
[126]Gan D J, Lu S Q, Song C S, et al. Physical properties of poly(aryl ether ketone)/mica composites: effect of filler content. Materials Letters, 2001, 48(5): 299-302
[127]Gan D J, Lu S Q, Song C S, et al. Mechanical properties and frictional behavior of a mica-filled poly(aryl ether ketone) composite. Polymer, 2001, 37(7): 1359-1365
[128]齐颖华,陈天禄,刘盛洲等.聚硫醚醚酮(砜)芳香环状低聚物的合成与自由基开环聚合[J].高等学校化学学报, 2000, 21: 480-483
[129]谌烈,宋才生,童永芬,温红丽,刘晓玲. 2,2',6,6'-四甲基-4,4'-二苯氧基二苯砜的合成与表征[J].江西师范大学学报(自然科学版), 2003, 28(1): 83-85
[130]Zolotukhin M G, Rueda D R, Balta Calleja F J, Cagiao M E, Bruix M, Sedova E A, Gileva N G. Aromatic polymers obtained by precipitation polyconden-sation: 4*. Synthesis of poly(ether ketone ketone). Polymer, 1997, 38: 1471-1476
[131]戴润英,宋才生,钟鸣,徐玲,黄红. 1,4-二(4-苯氧基苯甲酰基)苯的合成与表征[J].江西师范大学学报(自然科学版), 2007, 31(5): 518-522
[132]唐旭东,王艳,贺征华等.特种工程塑料聚芳醚酮的研究进展[J].天津科技44大学学报, 2006, 21(1): 29-32
[133]钟鸣,宋才生,童永芬等.含间苯基及甲基侧基聚芳醚砜醚酮酮的合成与表征[J].江西师范大学学报(自然科学版), 2005, 29(3): 193-195
[134]付长清,宋才生,刘勇军等.聚芳醚酮酮、聚芳醚醚酮酮无规共聚物的合成与性能研究[J].江西师范大学学报(自然科学版), 2005, 29(5): 377-380
[135]WEN Hong-li, SONG Cai-sheng, TONG Yong-fen, et al. Synthesis and properties of poly(aryl ether sulfene ether ketone ketone)(PESEKK). Journal of Applied Polymer Science, 2005, 96: 489-493
[136]Kelkar A J, Paul D R. Water vapor transport in a series of polyarylate. Journal of Membrane Science, 2001, 181: 199-212
[137]徐玲,宋才生,黄红等.高摩尔质量双酚A型聚芳酯的合成工艺研究[J].塑料工业, 2008, 36(4): 13-16
[138]汪薇,郭晓晖,林保平.双酚A型聚芳酯的相转移催化合成[J].化工时刊, 2004, 18(5): 35-41
[139]Harry R A, Frederick W L, Janes E M. Contemporary polymer chemistry.北京:化学工业出版社, 2006. 25-27
[140]王祖明,袁宝庆.芳香族聚酰胺纤维生产技术与应用[J].化工新型材料, 2004, 32(11): 1-5
[141]何伟,李振中,张文燕.聚酰胺复合材料增强增韧研究进展[J].中国塑料, 2006, 20(3): 1-6
[142]金国珍.工程塑料[M].北京:化学工业出版社, 2001. 420-425
[143]崔永丽,应鹏晨,王晓红.特种工程塑料聚芳醚酮[J].塑料工业, 2006, 34: 295-298
[144]谌烈,宋才生,童永芬,温红丽,刘晓玲.双邻位甲基取代的聚芳醚酮合成与表征[J].高分子学报, 2005, 1: 119-123
[145]莫志深,张宏放.晶态聚合物结构和X射线衍射[M].北京:科学出版社, 2003. 58-67
[146]Daniel R R, Mikhail G Z. Cold crystallization and polymorphismin an oligo(aryl ether ketone). Macromol. Chem. Phy., 1997, 198: 3517-3528
[147]Benjamin S H, Kenncorwin H, et al. Crystallization of poly(aryl ether ketone ketone) copolymers containing terephthalate/isophthalate moieties. Journal of Polymer Science, 1994, 32: 2585-2594
[148]Tianxi Liu, Zhishen Mo, Shanger Wang, Hongfang Zhang, Hui Na, Zhongwen Wu. Macromol. Rapid Commun, 1997, 18: 23-30
[149]柯扬船,吴忠文,郑玉斌.含间位取代苯基聚醚酮酮的结晶与晶体结构研究[J].高分子学报, 1997, 2: 177-182
[150]柯扬船,朱志宁,牟忠诚,吴忠文.聚醚酮酮及其低聚物晶体的多晶型结构[J].材料研究学报, 1997, 11(5): 491-495
[151]柯扬船,郑玉斌,王军佐,吴忠文.聚醚酮酮第Ⅱ晶型结构的WAXD研究[J].高分子材料科学与工程, 1997, 13(5): 85-90
[152]邱兆斌,莫志深,张宏放,盛寿日,宋才生.含间位聚醚酮醚酮酮的合成与结晶[J].应用化学, 1999, 16(5): 109-110
[153]苏爱华,汪爱莲.全对位聚芳醚酮酮的结晶行为[J].上饶师专学报, 1999, 19(3): 49-53
[154]Blundel D J, Newton A B. Variations in the crystal lattice of PEEK and related para-substituted aromatic polymers.Ⅱeffect of sequence and proportion of ether and ketone links. Polymer, 1991, 32: 308-313
[155]Gardner K H, Hsiao B S, Matheson R R. Structure, crystallization and morphology of poly(aryl ether ketone ketone). Polymer, 1992, 33: 2484-2495
[156]Ho Rongming, Cheng Stephen Z D, Hsiao B S. Crystal morphology and phase identifications in poly(aryl ether ketone)s and their copolymers. 1. Polymorphism in PEKK. Macromolecules, 1994, 27(8): 2136-2140
[157]Ho Rongming, Cheng Stephen Z D, Fisher H P. Crystal morphology and phase identifications in poly(aryl ether ketone)s and their copolymers. 2. Poly(oxy-1,4-phenylenecarbonyl-1,3-phenylenecarbonyl-1,4-phenylenene). Macromolecules, 1994, 27(20): 5787-5793
[158]Gadner K H, Hsiao B S, Faron Katherine L. Polymorphism in poly(aryl ether ketone)s. Polymer, 1994, 35: 2290-2295