含羧基侧基聚芳醚砜酮及环氧化改性研究
详细信息    本馆镜像全文|  推荐本文 |  |   获取CNKI官网全文
摘要
聚芳醚砜酮是分子主链上带有芳香族环和醚键、砜基、酮键的耐高温特种工程塑料。它具有优异的机械物理性能、阻燃、耐化学品腐蚀、耐剥离、耐辐射、耐水解、抗冲击、抗蠕变、绝缘稳定、和易加工等性能,近年来在高技术、民用及航空工业领域得到了广泛的应用和发展。
     本论文主要包括以下部分:
     1.利用自制的4,4'-二苯氧基二苯砜(DPODPS)、二苯醚(DPE)与对苯二甲酰氯(TPC)在无水AICl3和N,N-二甲基甲酰胺(DMF)的存在下,与1,2-二氯乙烷(DCE)一锅法进行低温溶液三元无规共缩聚,制得聚芳醚酮酮/聚芳醚砜醚酮酮(PEKK/PESEKK)树脂,并用1H-NMR, IR、DSC、TGA和耐溶剂性对其进行了表征分析。结果表明:聚合物具有预期的结构;对数比浓黏度(ηinh)均在0.65以上;随着PESEKK结构单元的增加,聚合物的Tg提高,结晶熔融峰在343℃并随着PEKK结构单元的比例的增加而提高:5%热失重在481℃以上,具有较高的耐热性能。聚合物只溶解于二氯乙酸、四氯乙烷等少数几种溶液,不溶解于常见溶剂,表现出较好的耐溶剂性能。
     2.以DPODPS和偏苯三酸酐酰氯(TMAC)为单体,在无水AICl3和N-甲基吡咯烷酮(NMP)的存在下,以1,2-二氯乙烷(DCE)为溶剂进行二元共缩聚,制得含羧基侧基的聚芳醚砜醚酮酮(PESEKK-A)树脂。用1H-NMR, FT-IR, TGA, DSC进行了表征分析。结果表明:聚合物具有预期的结构;且TMAC主要是以对位的链接方式为主;聚合物5%热失重为324.6℃;树脂具有优良的耐溶剂性和耐腐蚀性能。为树脂作为离子交换和吸附剂的基底材料提供了条件。PESEKK-A及其钠盐具有吸附金属离子的作用,是一种结构新颖的弱酸性阳离子交换树脂和吸附剂。
     3.以PESEKK-A的钠盐,环氧氯丙烷为原料,在四氯乙烷为溶剂和催化剂的条件下合成了含环氧侧基的聚芳醚砜醚酮酮(PESEKK-E)树脂,测出其环氧值在0.04-0.12之间,用4,4'-二氨基二苯砜(DDS)做固化剂,在一定温度下进行固化,用FT-IR, TGA, DSC对固化后的环氧树脂进行了表征分析。结果表明:聚合物具有预期的结构,固化后的各个主要峰的特征显示150℃/2h+180℃/2h+200℃/1h进行固化较好。由TG和DSC谱图分析得知,该树脂固化后分解温度在240~250℃范围内,通过环氧固化剂固化,树脂未出现玻璃化转变温度,可能是树脂的热分解温度低于其Tg的缘故。
     4.用自制的1,1'-二(4-羟基苯基)环己烷(环己基双酚)、过量的环氧氯丙烷在一定温度,和催化剂下作用生成表卤醇,再加入适量的氢氧化钠(NaOH)进行环化反应,制得了环己基双酚型环氧树脂,树脂为无色透明。采用FT-IR、1H-NMR对其结构进行了表征,并对其环氧值进行了滴定。用DDS做固化剂,在一定温度下进行固化,用FT-IR, TGA, DSC对固化后的环氧树脂进行了表征分析。结果表明:环氧树脂具有预期的结构。用盐酸-丙酮法滴定不同条件下合成的环氧树脂,环氧值最高为0.463.对合成的环氧树脂进行溶解性实验表明,树脂能溶于丙酮,卤代烃等常见的低沸点有机溶剂中,工艺性能良好。用DDS固化环己基双酚环氧树脂后,5%热失重在315℃以上,在220℃以前未出现玻璃化转变,可能是Tg高于初始热分解温度的缘故,耐热性能优良。
Ether sulfone ketone with the molecular main chain aromatic rings and ether, sulfone, ketone key special high temperature engineering plastics.It has excellent mechanical and physical properties, fire resistance, chemical corrosion resistance, peel resistance, radiation, hydrolysis, impact resistance, creep resistance, insulation and stability, easy processing properties, in recent years in high technology, civil and aviation Industry has been widely applied and developed
     The paper includes the following sections:
     1. Poly ether ketone ketone / poly ether sulfone ether ketone (PEKK/PESEKK) copolymer were synthesized from 4,4'-diphenoxy diphenylsulfone(DPODPS), diphenyl ether (DPE) and terephthaloyl chloride (TPC) in the presence of anhydrous aluminum trichloride(AlCl3), N,N-dimethylformamide(DMF) and 1,2-dichloroethane (DCE) by low temperature polycondensation. Copolymers were characterized by 1H-NMR, FT-IR, DSC and TGA. Their solubilities were also tested. The results showed that copolymers are expected, have high glass transition temperature and thermal stability. The inherent viscosity of the copolymers is more than 0.65 dL/g which conducted by Ubbelodhe viscometer and calculated by the One-Point Method. Copolymers have good chemical resistance only soluble in dichloroacetic acid, tetrachloroethane in room temperature even by heating.
     2 Poly ether sulfone ether ketone ketone with pendent carboxyl groups prepared from DPODPS and trimellitic anhydride chloride (TMAC) in the mixture solvent of N-methyl pyrrolidone (NMP) 1,2-dichloroethane (DCE), for anhydrous aluminum trichloride(AlCl3) as catalyst.'H-NMR and FT-IR characterized the chemical structures. The result carried on TGA show that the 5% weight loss was 324.6℃. Polymer has excellent solvent resistance. resistance for the ion exchange and adsorbent resin as base material of the conditions provided. PESEKK-A and its sodium salt with adsorption of metal ions, is a novel structure of the weak acid cation exchange resins and adsorbents.
     3. Poly ether sulfone ether ketone ketone containing epoxy groups (PESEKK-E) were obtained from PESEKK-A and epichlorohydrin, in the presence of tetrachloroethane and sodium hydroxide as catalyst. The values of epoxy are in the range 0.04 to 0.12 by titration. The heat curing strategy were investigated for 4,4'-diaminodiphenyl sulfone (DDS) as curing agent. The PESEKK-E was characterized by FT-IR, TGA and DSC. The results showed that:the polymer with the desired structure, curing characteristics of each of the major peaks showed 150℃/ 2h + 180℃/ 2h +200℃/ 1h for a better cure. Spectrum from the TG and DSC analysis showed that the decomposition temperature of the resin cured in the range of 240~250℃, through the epoxy curing agent, resin, glass transition temperature does not appear, may be the resin of the thermal decomposition temperature lower than Tg Reasons.
     4. 1,1-bis-(4-hydroxyphenyl)-cyclohexane was synthesized from cyclohexanone and phenol in the presence of HCl and mercaptoacetic acid as mixture catalysts. Then a novel transparent or light yellow epoxy resin was obtained from 1,1-bis-(4-hydroxyphenyl)-cyclohexane and epichlorohydrin for sodium hydroxide (NaOH) as catalyst. The chemical structure of the resulting Epoxy resin was characterized by FT-IR and 1H-NMR. The epoxy value of the titled resin was determined by the method of titration. The epoxy resin was cured by thermal curing, DDS as curing agent. The chemical structure of the cured Epoxy resin was characterized by FT-IR, thermal properties obtained from TGA and DSC. The results showed that epoxy resin was expected. With hydrochloric acid - acetone titration under different conditions, the synthesis of epoxy resin, epoxy value of up to 0.463. The solubility of the resulting polymers was also tested and it show that the epoxy resin can be dissolved in acetone, halogenated hydrocarbons and other common organic solvents. The process performance is good. DDS cured with double-cyclohexyl Phenol epoxy resin, the 5% weight loss at 315℃,220℃not previously appeared in the glass transition, Tg may be higher than the initial thermal decomposition temperature of the reason, over heat resistance.
引文
[1]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
    [2]李玉芳.特种工程塑料聚醚醚酮(PEEK)的开发和应用[J].国外塑料,2004,22(11):38-41
    [3]白杉,周洁.聚醚醚醚酮树脂的发展前景[J].技术与市场,2003,11:4-6
    [4]Huyx N, Hatsuo I. Poly(aryl-ether-ether-ketone) and its advanced composites: Areview[J]. Polymer Composites,1987,8(2):57-73
    [5]Fried JR.I:Mark J. editor.Poly (ether ether ketone).Oxford:Oxford University Press:1999.p466
    [6]孙永周,开展我国聚醚酮酮研究的建议[J].塑料工业.1990,(2):25-27
    [7]Bonner H W. US Pat.3065205 (1962)
    [8]Olah G A, Friedel-Crafts and Related Reactions,John Wiley and Sons L td. London,1964,3:1014-1020
    [9]Plast. Tech,1998,34(13):14-15
    [10]徐昌运.国外工程塑料现状与发展趋势[J].化工新型材料,1999,11:3-11
    [11]张万金,姬相玲,苑晶等.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].高等学校化学学报,1993,14(5):738-740
    [12]曹俊奎,苏文成,栾天罡等.刚性链嵌段共聚物的研究(Ⅳ)-聚醚醚酮)/酚酞基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
    [13]曹俊奎,苏文成,吴忠文等.刚性链嵌段共聚物研究(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
    [14]姬相玲,张万金,吴师等.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
    [15]曹俊奎,黄智华,吴忠文等.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
    [16]张海春,陈天禄.合成带有酞侧基的新型聚醚醚酮[P].中国专利,85108751.1987-06-03
    [17]李滨耀,庄国庆,张延等.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
    [18]刘彦军,赛锡高,刘圣军等.含二氮杂萘酮结构聚醚酮酮的合成及表征[J].高分子学报,1999,1:37-41
    [19]宋才生,蔡明中,周丽云等.低温溶液缩聚合成聚芳醚酮酮的研究[J].高分子学报,1995,17(1):99-103
    [20]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
    [21]蔡明中,宋才生,周丽云等.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,1993,34(10):486-488
    [22]黎苇,蔡明中,宋才生.4,4一二苯氧基二苯砜、4,4'一二苯氧基二苯酮、对苯二甲酞氯三元共聚物的合成[J].应用化学,2002,7:653—656
    [23]王千秋.邻苯二甲酸二辛酯的催化研究进展[J].河北化工,2004,2:11-12
    [24]樊云峰.国内外邻苯二甲酸异辛酯的发展状况[J].精细石油化工,1999,2:4-7
    [25]鲁凤兰.无毒增塑剂的生产与应用[J].精细石油化工进展,2006,7(9):40-45
    [26]Nadia L jungberg, Bengt Wesslen. Tributyl citrate oligomers as plasticizers for poly (lactic acid):thermo-mechanical film properties and aging [J].Polymer, 2003,44 (25):7679-7688
    [27]王化淳,董秀芹.偏苯三酸三辛酯工业技术探讨[J].现代化工,1998,18(2):30-33
    [28]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].天津科技大学学报,2006,21(1):29-32
    [29]林权,王一凡,张万金等.含间苯基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,1996,17:1965
    [30]曹俊奎,苏文成,朴明俊等.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
    [31]王军佐,郑玉斌,张万金等.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
    [32]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
    [33]YueZhong M, Ant i sar RH, Hay AS. J Polym Sc i. A:Polym. Chem.,1999, 37:1781-1788
    [34]Trotta F, Droili E, M oraglio G, et al. J of Applied Polym Sci.,1998,70:477-482
    [35]廖功雄,李荃.含硫醚和二氮杂萘酮结构聚芳醚酮的合成与性能[J].高分子学报,2002,5:641-646
    [36]盛寿日,罗秋燕,霍毅等.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[J].高分子材料科学与工程,2006,22(3):85-87,92,87
    [37]高自宏,范星河等.新型含硅聚芳醚酮的合成与表征[J].高等学校化学学报,2005,26(8):1579-1581
    [38]Hay A S. Polymers derived from phenolphthaleine [P].US Patent, 5254663.1993-10-19
    [39]Jian X G, Cheng L. Synthesis of all-aromatic polyamides containing the 1,2-dihydro-4-phenyl(2H) phtha-lazone moiety[J]. Polym. Sci., Part A:Polym. Chem.,1999,37(11):1565-1567
    [40]Liao G X, Jian X G, Guo X Y, et al. Synthesis and Properties of Polyetherketones Containing Sulfide and Phthalazinone[N].Chin. Chem. Lett.,2002,13(7): 607-608
    [41]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
    [42]王国庆,朱秀玲,张守海等.一种杂环磺化聚芳醚睛酮质子交换膜材料的合成及表征[J].高分子学报,2006,2:209-212
    [43]张善举,那辉,郑玉斌等.单酚脱盐法联苯聚醚酮的合成[J].高分子材料科学与工程,1997,13(3):36-40
    [44]孙辉,吴忠文,郑玉斌等.一种新型聚芳醚酮的热致液晶行为[J].高等学校化学学报,1999,20(12):1985-1986
    [45]高晔,赛锡高.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
    [46]李秀华,孟跃中,赛锡高.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):37-39,42
    [47]陈连周,赛锡高.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
    [48]张守海,杨大令,赛锡高.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,2002,23(12):2382-2385
    [49]Ritter H, Thorwirth R, Muller G Comb-like poly(aryl-ether-ketones) containing naphthalene moieties in the main chain[J]. Die Makromolekulare Chemie, 194(5):1469-1481
    [50]王贵宾,陈春海,周宏伟等.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
    [51]刘佰军,陈春海,呼微等.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
    [52]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
    [53]Mohanty D K, Lin T S, Ward T C, et al. Novel Synthesis of Thermoplastic Semicrystalline Poly (Arylene Ether Ketone)[C]. Materials Science for the Future:31st International SAMPE Symposium and Exhibition. USA:California, 1986.945-955
    [54]盛寿日,周丽云,瞿志荣等.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
    [55]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
    [56]赛锡高,陈连周,朱秀玲等.新型杂环氯代聚芳醚酮的合成与性能[J].材料研究学报,2001,15(5):500-504
    [57]Bennett G S, Farris R J, Thompson S A. Amine-terminated poly(aryl ether ketone)-epoxy/amine resin systems as tough high performance materials[J]. Polymer,1991,32(9):1633-1641
    [58]Yonezawa N, Mori S I, Miyata S, etal. Synthesis of aromatic poly (ether ketone)s having adhesion property to steel surface[J]. React. Func. Polym.,2002,53(1): 11-17
    [59]郭庆中,王红华,景凤英等.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
    [60]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].南昌:江西师范大学,2004
    [61]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].南昌:江西师范大学,2004
    [62]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(16):2881-2887
    [63]Kim J P, Lee W Y, Wook K, et al. Fluorinated poly(arylene ether sulfide) for Polymeric optical Waveguide Devices[J]. Macromolecules,2001,34(22): 7817-7821
    [64]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., PartA:Polym. Chem.,1999,37(14):2355-2361
    [65]Tan B, Vasudevan V, Lee Y J, et al. Design and characterization of thermosetting polyimide structural adhesive and composite matrix systems[J]. Polym. Sci., Part A:Polym. Chem.,1997,35(14):2943-2954
    [66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
    [67]吴雪梅,贺高红,顾爽等.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
    [69]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[J]. MaterialsLetters,2006,60(11):1369-1373.
    [70]Hunter R A, Turner P D, Rimmer S. Suspension cross-linking of poly(aryl ether ketone)s containing carboxylic acid funictionality[J]. Mater. Chem.,2001, 11:736-740
    [71]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.,2002,88(5):1111-1114
    [72]Jikei M, Kakimoto M. Hyperbranced polymers:a promising new class of materials [J]. Prog. Polym. Sci.,2001,26(8):1233-1285
    [73]Gao C, Yan D. Hyperbranched polymers:from synthesis to applications [J]. Prog. Polym. Sci.,2004,29(3):183-275
    [74]Hawker C J, Chu F K. Hyperbranched poly(ether ketones):Manipulation of Structure and Physical Properties [J]. Macromolecules,1996,29(12):4370-4380
    [75]Shu C F, Leu C M. Hyperbranched Poly(ether ketone) with Carboxylic Acid Terminal Groups:Synthesis, Characterization, and Derivatization[J].Macromolecules,1999,32(1):100-105
    [76]Song Y C, Chang Y, Kim J S, et al. Hyperbranched Poly(ether ketone)Analogues with Heterocyclic Triazine Moiety:Synthesis and Peripheral Functionalization[J]. Macromol. Chem. Phys.,2001,202 (2):263-269
    [77]牟建新,陈杰,张春玲等.B3型单体及超支化聚醚醚酮的合成及表征[J].吉林大学学报(理学版),2005,43(5):662-665
    [78]Baek J B, Tan L S. Hyperbranched Poly(phenylquinoxaline-ether-ketone) Synthesis in Poly(phosphoric acid)/P2O5 Medium:Optimization and Somelnteresting Observations [J]. Macromolecules,2006,39(8):2794-2803
    [79]Wang D H, Baek J B, Tan L S. Grafting of vapor-grown carbon nanofibers(VGCNF) with a hyperbranched poly(ether-ketone)[J]. Mate. Sci. Eng.,2006,132(1-2):103-107
    [80]张云鹤,王冬,朱业明等.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
    [81]Frank W M, Matilda M F, Martin T M. Synthesis and characterization of fluorinated poly(aryl ether ketone)s containing 1,4-naphthalene moieties[J]. Polym. Sci., PartA:Polym. Chem.,1997,35(3):521-526
    [82]James H C, James E D. Trifluoromethylated poly(ether ether ketone)s[J].Polymer, 1994,35(23):5124-5129
    [83]Mercer F W, Fone M M, Reddy U N. Synthesis and characterization of fluorinated poly ether ketones prepared from decafluorobenze phenone[J]. Polymer,1997,38(8):1989-1995
    [84]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
    [85]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[J].Mater. Chem. Phys.,2006,99(2-3):465-469
    [86]Malik T M. Thermal and mechanical characterization of partially miscible blends of poly(ether ether ketone) and polyethersulfone[J]. Appl. polym. Sci., 1992,46(2):303-310
    [87]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
    [88]Musto P, Karasz F E, Macknight W J. Hydrogen bonding in polybenzimidazole/polyimide systems:a Fourier-transform infra-red investigation using low-molecular-weight monofunctional probes [J]. Polymer, 1989,30(6):1012-1021
    [89]Harris, J E, Robeson, L M. Blends of poly (aryl ketones)[P]. US Patent,4609714. 1986-09-02
    [90]Harris, J E, Robeson, L M. Miscible blends of poly (aryl ether ketone)s and polyetherimides[J]. App. Polym. Sci.,1988,35(7):1877-1891
    [91]何伟,廖功雄,曲敏杰等.PPESK/PTFE共混物摩擦行为研究[J].中国塑料,2006,20(2):34-37
    [92]Stuart B H, Briscoe B J. Scratch Hardness Studies of poly (ether ether ketone)[J].Polymer,1996,37(17):3819-3824
    [93]Hanchi J, Eiss N S. Synergistic Friction and Wear of Ternary Blends of PEEK, PEI and a TLCP at Elevated Temperatures[J]. Tribology Trans.,1997,40(1): 102-110
    [94]宣英男,黄勇,赛锡高等.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
    [95]Kuo M C, Huang J C, Chen M. Non-isothermal crystallization kinetic behavior of alumina nanoparticle filled poly (ether ether ketone)[J]. Mater. Chem. Phys., 2006,99(2-3):258-268
    [96]He W, Liao G X, Jian X G et al. Dynamic mechanical thermal behavior of novel Poly (phthalazinone ether sulfone ketone) and poly(tetrafluoroethylene) blends[J].Polym. Eng.,2006,26(6):617-631
    [97]那辉,苑晶,倪宏伟等.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
    [98]盛寿日,蔡明中,宋才生等.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
    [99]孟跃中,张世振,张宏书等.嵌段半结晶聚芳醚酮及其合成方法[P].中国专利,01107474.2001-07-25
    [100]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
    [101]Francis B, Thomas S, Jose J, et al. Hydroxyl terminated poly(ether ether ketone)with pendent methyl group toughened epoxy resin:miscibility, morphology and mechanical properties [J]. Polymer,2005,46(26):12372-12385
    [102]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 [J]. International Journal of Polymeric Materials,2006, 55(9):681-702
    [103]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 butyl groups [J]. Polymer,2006,47(15):5411-5419
    [104]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(3):541-556
    [105]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
    [106]曲敏杰,赛锡高.钛酸钾晶须填充新型聚芳醚酮的性能[J].中国塑料,200216(6):27-30
    [107]Davim J P, Reis P, Lapa V Machinability study on poly ether ether ketone(PEEK) unreinforced and reinforced(GF30) for applications in structural components[J]. Comp. Struc.,2003,62(1):67-73
    [108]Gan D, Cao W, Song C, et al. Mechanical properties and morphologies of poly(ether ketone ketone)/glass fibers/mica ternary composites[J]. Mater. Lett., 2001,51 (2):120-124
    [109]Sung I M, Monson L L, Extrand C W Insert-molded poly(ether imide)/carbon fiber poly(ether ether ketone) bimaterial composites:Fracture and interfacial analysis[J]. Appl. Polym. Sci.,2006,102(3):2362-2371
    [110]Ezquerra T A, Zolotukhin M, Privalko V P, et al. Relaxation behavior in model compounds of poly (aryl-ether-ketone-ketone) as revealed by dielectricspectroscopy [J]. Chem. Phys.,1999,110(20):10134-10140
    [111]Goyal R K, TiwariA N, Mulik U P, et al. Anisotropic linear thermal expansivity of poly(ether-ether-ketone)[J]. Europ. Polym. J.,2006,42(10):2888-2893
    [112]Ohmori M, Kimura K, Yamashita Y et al. Consideration of Solvent Effect on Precipitation Polymerization of Poly(ether-ketone)s via Friedel-Craft Acylation[J].Fiber,2006,62(7):141-149
    [113]Zhao H X, Robert K Y L. Fracture behaviour of poly (ether ether ketone) films with different thicknesses[J]. Mech. Mater.,2006,38 (1-2):100-110
    [114]Chen J, Liu X C, Yang D C. Rheological properties in blends of poly(aryl ether ether ketone) and liquid crystalline poly(aryl ether ketone)[J]. Appl. Polym. Sci., 2006,102(4):4040-4044
    [115]Abu Bakar M S, Cheang P, Khor K A. Tensile properties and microst ructural analysis of spheroidized hydroxyapatite-poly (ether ether ketone) biocomposites[J].Materials Science and Engineering A,2003,345:55263
    [116]Abu Bakar M S, M H W Cheng, S M Tang, et al.Tensile properties, tension-tension fatigue and biological response of olyetherather ketone-hydroxyapatite composites for load-bearing ort hopedic implants[J].Biomaterials,2003,24 (13):2245-2250
    [117]Kuo M C, Tsai C M,Huang J C,Chen M. PEEK composites re-inforced by nano-sized SiO2 and Al2O3 particulates[J].Materi-als Chemistry and Physics, 2005,90:185-195
    [118]Goyal R K, Tiwari A N, Mulik U P,Negi Y S. Effect of alumi-num nit ride on thermomechanical properties of high performance PEEK Composites:Part A [J].Applied Science and Manufacturing,2007,38 (2):516-524
    [119]陈祥宝.化学工业出版社[M].1999.《高性能树脂基体》:213-214
    [120]阮汝祥,姜振华,王贵宾等.聚醚醚酮/聚醚醚酮酮共混体系的熔融和等温结晶行为[J].高等学校化学学报,2000,21(7):1130-1133
    [121]Kh G, Thomas S, Yang Z G et al. Failure behavior and performance analysis of hybrid-fiber reinforced PAEK composites at high temperature [J]. Composites Sci. Tech.,1997,58(9):1509-1518
    [122]Gan D J, Lu S Q, Song C S, et al. Physical properties of poly(ether ketone ketone)/mica composities:effect of filler content[J]. Mater. Lett.,2001, 48(5):299-302
    [123]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,2000,48(3):480-483
    [124]Abderrazak B H, Howard M C, Philip H, et al. Synthesis of a Catechol-Based Poly(ether ether ketone) ("o-PEEK") by Classical Step-Growth Polymerization and by Entropically Driven Ring-Opening Polymerization of Macrocyclic Oligomers[J].Macromolecules,2006,39(19):6467-6472
    [125]孙勤良,日本环氧树脂最新发展概况[J].热固性树脂,10(4),54-56,1995
    [126]姚康德,刘静,高性能环氧树脂的进展[J].热固性树脂,7(3),52-57.1992
    [127]陈平,刘胜平.环氧树脂[M].北京:化学工业出版社,1999.198-201
    [128]金林生,许红,环氧树脂的高性能化[J],热固性树脂,13(4),37-41,1998
    [129]Kuntman A, Kuntman A H. Study on dielectric properties of a new polyimide film suitable forniterlayer dielectric material in microelectronics applications[J]. Microelectronics Journal,2000,31:629-638
    [130]宋谦.环氧灌注材料在电子器件上的应用及发展动向[J].电子工艺技术,2001,22(3):47-50
    [131]梁国正,顾媛娟.合成树脂与塑料工业[M].北京:化学工业出版社,1999.248
    [132]丁孟贤,何白天.聚酰亚胺新型材料[M].北京:科学出版社,1998.351
    [133]Xu J M. Plastic electronics and future trends in microelectronics [M]. New York:Synthetic metals,2000.115
    [134]Rimdusit S, Ishida H. Development of new class of electronic packaging materials based on ternary systems of benzoxazine, epoxy, and phenolic resins[J]. Polymer,2000,41:7941-7949
    [135]韦春,谭松庭,王霞瑜.热致性液晶增韧环氧树脂的研究进展[J].材料工程,2002,2:3-5
    [136]孙勤良.环氧树脂在封装材料中的应用概况[J].热固性树脂,2000,15(1):47-51
    [137]胡幼华,高辉,叶士标,何宁德.环氧树脂材料的研究概况[J].绍兴文理学院学报,2000,20(6):56-61
    [138]夏青.国内外环氧树脂生产及市场[J].化工科技,2001,9(6):67-70
    [139]吕程,牟其伍.含环氧键的液晶高分子改性环氧树脂的研究[J].材料导报网刊,2008,3(2):20-21
    [140]华幼卿,王惠琼.聚醚砜改性环氧树脂的研究:(II)力学性能和热性能[J].北京化工学院学报,1992,19(1)23-29
    [141]杨立平.聚砜增韧环氧树脂固化反应动力学的研究[D][硕士论文].北京:北京化工大学材料物理与化学,2007
    [142]吴忠文.特种工程塑料聚芳醚酮[J].化工新型材料,1999,11:18-20
    [143]Buchnal C B, Gibert A H. Toughening tetrafunctional epoxy resins using polyethrimde. Polymer,1989.30:213-217
    [144]Hedrick J H, Yilgor I.Bonding properties of epoxy resin containing mesogenic group.Polym Bull,1985,13:201-204
    [145]Hedrick J L, LEWIS D.Novel rapid cure adhesive for low temperature using thiirane compound. Polym Prep Am Chem Soc Div Polym Chem,1988,29: 363-367
    [146]周丽云,盛寿日,蔡明中,宋才生,二苯醚-对苯二甲酰氯-4,4’-二苯氧基二苯砜三元共聚物的合成与性能[J].应用化学,1998.10(5),6-9
    [147]占玉林.聚芳醚砜醚酮酮树脂的合成工艺研究[D]:[硕士学位论文].江西:江西师范大学化学化工学院,2009
    [149]Robeson L M, Tibbitt J M. History of polyarylates, High performance polymers: their origin and developments[M]. Seymour, R. B. Krishenbaum, G S. Eds. Elsvier:Amsterdam,1986,95-103
    [150]Urich H H, Rafler G Sulfonated poly (aryl ether ketone)s[J]. Die Angewandte Makromolekulare Chemie,1998,263:71-78
    [151]Li Xiangfeng, Liu Changpeng, Lu Hui, et al. Preparation and characterization of sulfonated poly(ether ether ketone ketone) proton exchange membranes for fuel cell application[J]. Journal of Membrane Science,2005,255(1-2):149-155
    [152]Peixiang X, Gilles P R, Michael D q et al. Synthesis and characterization of sulfonated poly (ether ether keone) for proton exchange membranes [J]. Journal of Membrane Science,2004,229(1-2):95-106
    [153]Udea M, Toyota H, Onchi T. Synthesis and characterization of aromatic poly(ether sulfone)s containing pendent sodium sulfonate groups[J]. Polym. Sci., PartA:Polym. Chem.,1993,31(4):853-858
    [154]Wang F, Roovers J, Toporowski PM. Synthesis and molecular characterization of narrow molecular weight distribution fractions of methyl-substituted poly(aryl ether ether ketone)[J]. Macromolecules,1993,26(15):3826-3832
    [155]Mikehail G Z, Howard M C, Lionel G S One-pot synthesis and characterization of soluble poly (aryl ether-ketone)s having pendant carboxyl groups[J].Macromolecules,2003,36(13):4766-4771
    [156]程彩霞,刘晓玲,宋才生.制备含羧基侧基聚芳醚酮酮树脂的初步探索(I)[J].江西师范大学学报,自然科学版,2002,26(1):60-63
    [157]谢光亮,廖贵红,吴方娟等.羧侧基聚芳醚飒醚酮酮的合成及其吸附性能[J].应用化学,2008,25(3):295-299
    [158]区美鸿,邢春明,李永先.塑料手册[M].兵器工业出版社,1991,407-413

© 2004-2018 中国地质图书馆版权所有 京ICP备05064691号 京公网安备11010802017129号

地址:北京市海淀区学院路29号 邮编:100083

电话:办公室:(+86 10)66554848;文献借阅、咨询服务、科技查新:66554700