联苯二酚系列产品开发及联苯类液晶材料合成研究
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摘要
3,3′,5,5′-四甲基联苯二酚(TMBP)是一种重要的有机中间体,可用作聚酯﹑聚氨酯﹑聚碳酸酯﹑聚砜﹑环氧树脂等诸多产品的改性单体;也可用作橡胶﹑乳剂防老剂和塑料抗氧剂,以及染料中间体或石油制品的稳定剂。本实验提供了一种制备3,3′,5,5′-四甲基联苯二酚的新方法,即以2,6-二甲基苯酚为原料,在水介质中采用双氧水做氧化剂,通过氧化偶合反应和还原反应,两步法合成3,3′,5,5′-四甲基联苯二酚;另外还探讨了氧化剂和催化剂对产物收率的影响,经过反复实验得出最佳工艺条件为:2,6-二甲基苯酚:双氧水:催化剂=1:2:0.00018(摩尔比),氧化偶合反应温度为80℃,氧化反应时间为3h,还原反应温度为80℃,还原反应时间为0.5h,产品产率和纯度分别可达80%和99%以上。此合成方法在工业中具有很好的应用前景。
含联苯结构的环氧树脂是一种具有液晶性的环氧树脂,具有许多优异的性能。本文采用新的方法合成了环氧树脂改性单体-3,3′,5,5′-四甲基联苯-4,4′-二羟乙基醚;用三种方法合成了3,3′,5,5′-四甲基联苯二酚二缩水甘油醚,并对三种方法的反应步骤,原料,反应条件,产率和后处理进行了讨论;此外,还合成了4,4′-双(2-羟基乙基)-3,3′,5,5′-四甲基联苯二缩水甘油醚(BP1)和4,4′-双(4-羟基苯甲氧基)-3,3′,5,5′-四甲基联苯二缩水甘油醚(BP2)两种联苯环氧树脂。
联苯结构的液晶是目前应用最广泛的一种液晶材料,本文以3,3′,5,5′-四甲基联苯二酚为原料设计并合成了八个对称联苯双酯类液晶化合物,它们的介晶性通过差示扫描量热仪(DSC),X-射线衍射仪(XRD)和热台偏光显微镜(POM)进行了研究;并测定了4,4′-3,3′,5,5′-四甲基联苯-二(4-甲基苯甲酸酯)(Ⅲa)的单晶结构,结果显示:晶体属于单斜晶系,P2_1/C空间群,晶胞参数为a=18.525(3)(A|°),b=12.196(2)(A|°),c=12.195(2)(A|°),(A|°)=97.142(2)°,V=2733.7(9)(A|°)~3,Z=4,D_c=1.163 Mg/m~3,R=0.0521, R_W=0.1161。化合物均为热致型互变液晶,并讨论了氧原子、不饱和端基和端基链长对介晶性的影响。
3,3′,5,5′-tetramethyl-diphenol(TMBP) is an important organic intermediate of dye which can be used as modified monomers of polyester, polyurethane, polycarbonate, polysulphone, epoxy resin and so on. Also used for the stabilizer of rubber, emulsion, plastic and some petroleum products. This experiment provided a new synthetic route of TMBP. It was synthesized from 2,6-dimethylphenol by two-step method which are oxidative coupling and reduction reaction, hydrogen peroxide was used as oxidant in the water. The effect of oxidant and catalyst on product was studied, The optimum process was determined and was that 2, 6-dimethylphenol: oxydol: catalyst= 1: 2: 0.00018 (molar ratio), the temperature and time of oxidative coupling are 80℃and 3h, the temperature and time of reduction reaction are 80℃and 0.5h, the yield and purity are above 80% and 99% respectively. The method is very useful from the industrial point of view.
Epoxy resin containing biphenyl structure is a kind of liquid crystal epoxy resin. 3,3′,5,5′-tetramethyl-4,4′-di(2-hydroxyethanyoxy)-biphenyl as a modified monomer of epoxy resin was synthesized by a new synthesis method in this article. Also 3,3′,5,5′-tetramethyl- diphenyldiglycidyl ether was synthesized by three methods. Reaction steps, raw material, reaction conditions, yield and treatment processes of three methods were studied. Then two epoxy resins containing biphenyl structure were synthesized, They are 4,4′-bis(2-hydroxylethyl)-3,3′,5,5′-tetramethylbiphenyl(BP1) and 4, 4′-bis( 4-hydroxybenzoyloxy ) -3,3′,5,5′-tetramethylbiphenyl (BP2).
At present biphenyl liquid crystals are widely used. Eight symmetrical diphenylnate liquid crystals were prepared from 3,3′,5,5′-tetramethyl-diphenol in this article. Their liquid crystal properties were tested by differential scanning calorimetry (DSC), X-ray diffraction (XRD) and hot stage polarizing microscop (POM). The crystal structure ofⅢa was detemfined by single crystal X-ray diffraction techniques,Ⅲa is a monoclinic crystal system, space group P2_1/C with the unit cell parameters: a=18.525(3)(A|°), b=12.196(2)(A|°), c=12.195(2)(A|°),(A|°)=97.142(2)°, V=2733.7(9)(A|°)~3, Z=4, D_c=1.163 Mg/m~3, R=0.0521, R_W=0.1161. The results showed that molecules lead thermotropic liquid crystals properties. The relations among the mesomorphism, oxygen atoms, terminal unsaturated bond, the flexible chain length were investigated.
含联苯结构的环氧树脂是一种具有液晶性的环氧树脂,具有许多优异的性能。本文采用新的方法合成了环氧树脂改性单体-3,3′,5,5′-四甲基联苯-4,4′-二羟乙基醚;用三种方法合成了3,3′,5,5′-四甲基联苯二酚二缩水甘油醚,并对三种方法的反应步骤,原料,反应条件,产率和后处理进行了讨论;此外,还合成了4,4′-双(2-羟基乙基)-3,3′,5,5′-四甲基联苯二缩水甘油醚(BP1)和4,4′-双(4-羟基苯甲氧基)-3,3′,5,5′-四甲基联苯二缩水甘油醚(BP2)两种联苯环氧树脂。
联苯结构的液晶是目前应用最广泛的一种液晶材料,本文以3,3′,5,5′-四甲基联苯二酚为原料设计并合成了八个对称联苯双酯类液晶化合物,它们的介晶性通过差示扫描量热仪(DSC),X-射线衍射仪(XRD)和热台偏光显微镜(POM)进行了研究;并测定了4,4′-3,3′,5,5′-四甲基联苯-二(4-甲基苯甲酸酯)(Ⅲa)的单晶结构,结果显示:晶体属于单斜晶系,P2_1/C空间群,晶胞参数为a=18.525(3)(A|°),b=12.196(2)(A|°),c=12.195(2)(A|°),(A|°)=97.142(2)°,V=2733.7(9)(A|°)~3,Z=4,D_c=1.163 Mg/m~3,R=0.0521, R_W=0.1161。化合物均为热致型互变液晶,并讨论了氧原子、不饱和端基和端基链长对介晶性的影响。
3,3′,5,5′-tetramethyl-diphenol(TMBP) is an important organic intermediate of dye which can be used as modified monomers of polyester, polyurethane, polycarbonate, polysulphone, epoxy resin and so on. Also used for the stabilizer of rubber, emulsion, plastic and some petroleum products. This experiment provided a new synthetic route of TMBP. It was synthesized from 2,6-dimethylphenol by two-step method which are oxidative coupling and reduction reaction, hydrogen peroxide was used as oxidant in the water. The effect of oxidant and catalyst on product was studied, The optimum process was determined and was that 2, 6-dimethylphenol: oxydol: catalyst= 1: 2: 0.00018 (molar ratio), the temperature and time of oxidative coupling are 80℃and 3h, the temperature and time of reduction reaction are 80℃and 0.5h, the yield and purity are above 80% and 99% respectively. The method is very useful from the industrial point of view.
Epoxy resin containing biphenyl structure is a kind of liquid crystal epoxy resin. 3,3′,5,5′-tetramethyl-4,4′-di(2-hydroxyethanyoxy)-biphenyl as a modified monomer of epoxy resin was synthesized by a new synthesis method in this article. Also 3,3′,5,5′-tetramethyl- diphenyldiglycidyl ether was synthesized by three methods. Reaction steps, raw material, reaction conditions, yield and treatment processes of three methods were studied. Then two epoxy resins containing biphenyl structure were synthesized, They are 4,4′-bis(2-hydroxylethyl)-3,3′,5,5′-tetramethylbiphenyl(BP1) and 4, 4′-bis( 4-hydroxybenzoyloxy ) -3,3′,5,5′-tetramethylbiphenyl (BP2).
At present biphenyl liquid crystals are widely used. Eight symmetrical diphenylnate liquid crystals were prepared from 3,3′,5,5′-tetramethyl-diphenol in this article. Their liquid crystal properties were tested by differential scanning calorimetry (DSC), X-ray diffraction (XRD) and hot stage polarizing microscop (POM). The crystal structure ofⅢa was detemfined by single crystal X-ray diffraction techniques,Ⅲa is a monoclinic crystal system, space group P2_1/C with the unit cell parameters: a=18.525(3)(A|°), b=12.196(2)(A|°), c=12.195(2)(A|°),(A|°)=97.142(2)°, V=2733.7(9)(A|°)~3, Z=4, D_c=1.163 Mg/m~3, R=0.0521, R_W=0.1161. The results showed that molecules lead thermotropic liquid crystals properties. The relations among the mesomorphism, oxygen atoms, terminal unsaturated bond, the flexible chain length were investigated.
引文
[1]杨山跃,赵美法.化工科技市场, 2005, 12, 33.
[2]王雨来.新技术新产品新工艺, 2001, (4), 24.
[3] .Shigeru Tsuruya, Yasushi Kishikawa, Ryozo Tanaka. Journal of Catalysis, 1977, 49, 254.
[4] .Anna M Schuitema, Peternity G Aubel, Iryna A. Inorganica Chimica Acta, 2003, 355, 374.
[5] .Mieke Huisman, Iryna A Koval, Patrick Gamez, Jan Reedijk. Inorganica Chimica Acta, 2006, 359, 1786.
[6]蒋忠良,汪正发,马东旭.同济大学学报, 2002, 30(7), 904.
[7] Sagar Sharma, Nilotpal Barooah, Jubaraj Baruah. Journal of Molecular Catalysis A Chemical, 2005, 229, 171.
[8] .Bo Xiao, Hongwei Hou, Yaoting. Journal of Organometallic Chemistry, 2007, 692, 2014.
[9]朱杰,孟祥光,臧蓉蓉,陈民助.催化学报, 2005, 26(4), 317.
[10] .Inui Naoki, Kikuchi Taketoshi, Tanaka Shinya. [P] WO9946227, 1999, 09.
[11] .W. L. Carrick, G. L. Karapinka, G. T. Kwinatkowski. The Journal of Organic Chemistry , 1969, (34), 2388.
[12]凌有道,吕满庚,任少平. [P] CN 1706782, 2005, 12.
[13]刘群,申屠宝卿,翁志学.高校化学工程学报, 2008, 22(5), 906.
[14] Christophe Boldron, Guillem Aromi, Ger Challa. Chemical Communications(Cambridge, United Kingdom), 2005, (46), 5808.
[15] .Mohamed Sarakha, Michele Bolte. Journal of Photobiology A:Chemistry, 1996, (97), 87.
[16] .C.E.Sroog. Progr Polym Sci, 1991, 16(4), 561.
[17]程晖,何尚锦,张保龙.热固性树脂, 1999, 1, 16.
[18] .Chun-Fang Li, Dong-Xiang Li, Sheng-Yu Feng. Polym Int, 2005, (54), 1041.
[19]汪多仁. [M]溶剂与专用化学品生产配方和合成工艺,北京:科学技术文献出版社, 2003.
[20]刘凉冰.弹性体, 1999, 9(3), 41.
[21] .Brennan, Michael E. [P] US.4500655, 1985, 2.
[22]周建. [P] 200810010725, 2008, 8.
[23] .Harris Eugene G. [P] US.4533759, 1985.
[24]范存良,杨忠保,单根林,奚军.石油化工, 1999, 28(4), 250.
[25]张少钢,吴石良,林仪智,叶军明.精细化工, 2001, 18(12), 741.
[26]孙冬兵,王树清,高崇.精细石油化工进展, 2008, 9(11), 24.
[27]李斌,席海涛,孙小强.化学试剂, 2003, 25(1), 29.
[28]崔晓静,刘承美,程晓菊.精细石油化工, 2003, (2), 42.
[29]蒋青,陈益钊,李聚才,李文藻,郁陵庄.化学试剂, 1993, 15(4), 246.
[30]张有明,李攀,张鹏云,刘志铭,魏太保.化工新型材料, 2010, 38(2), 115.
[31]陈平,刘胜平. [M]环氧树脂,北京:化学工业出版社, 1999.
[32]伍敏扬.化工新型材料, 1999, 27(3), 22.
[33]石宁.热固性树脂, 2000, 15(2), 30.
[34]陈立新,蓝立文,王汝敏.材料导报, 2000, 14(9), 41.
[35]左瑞霖,常鹏善,解云川,陈建平.高分子材料科学与工程, 2002, 18(4), 6.
[36]刘国栋,李卿,高俊刚,张留成.高分子材料科学与工程, 2008, 24(10), 12.
[37]李冰.化工技术与开发, 2009, 38(3), 29.
[38]刘伟昌,申胜军,刘德山.高分子通报, 1998, (3), 59.
[39] .Carfagna C, Amendola E, Gramberm M. J Mater Sci Let, 1994, 13, 126.
[40] .Carfagna C, Nicolaiai L, Amendola E. Journal of applied Polymer science, 1992, 44(8), 1465.
[41] .Sue H J, Earla J D , Hefner R E Jr. Journal of materials science, 1997, 32(15),4031.
[42]肖潇.科技资讯, 1998, (19), 11.
[43]吴良义.热固性树脂, 2000, 15(4), 21.
[44] .Roland G, Heinrich H, Hanns P M, DE 3622610(EP252358, USP 4764581), 1986.
[45]杨小王,陆绍荣,虞锦洪,吴兵.高分子材料科学与工程, 2008, 24(2), 39.
[46]刘伟昌,申胜军.清华大学学报(自然科学版), 1998, 38(12), 104.
[47]陈立新,王汝敏,蓝立文.玻璃钢/复合材料, 2000, 2, 28.
[48]液晶环氧树脂研究在国外取得新成果.摘自“中国化工信息网”.
[49] .Vyazo S, Mitite A, Sbirra N. Macromol Rapid Commun, 2003, 18(24), 1060.
[50] .Prakaipetch P, Veronica A, Marta G. Polymer, 2002, 43(3), 839.
[51]谢东.科技潮, 1998, (11) , 46.
[52]李帅,任培兵,仲锡军,段二红,赵地顺.河北化工, 2008, 9(31), 28.
[53] .F. Reinitzer. Montash Chem, 1888, 9, 421.
[54] .G. Friedel, Ann. Physique(Paris), 1922, 18, 273.
[55] .A. J. Bosman, E. E. Havinga. Phys. Rev, 1963, 129(4), 1593.
[56] .E.Bose. Z.Phys, 1909, 10, 230.
[57] .V.Grandjean. Z. Phys, 1911, 12, 1011.
[58]王良御,廖松生. [M]液晶化学,北京:科学出版社, 1988.
[59]汪朝阳.化工时刊, 2002, (11), 25.
[60]吴大诚,谢新光,徐建军. [M]高分子液晶,成都:四川教育出版社, 1988.
[61]郭强. [M]液晶显示应用技术,北京:电子工业出版社, 2000.
[62]杨柏梁.液晶与显示, 2000, 2(15) , 154.
[63]谈漫琪,丁学泉. [M]液晶知识,北京:科学普及出版社, 1984.
[64]张文志.科技信息, 2007, 19, 46.
[65]刘铸晋. [M]液晶的性质和应用,上海:科学技术文献出版社, 1981, 5.
[66]周其凤,王新久. [M]液晶高分子,北京:科学出版社, 1999.
[67]徐晓鹏,底楠.化工新型材料, 2006, 34(11) , 81.
[68]范程士.安徽大学研究生学位论文, 2005.
[69] . [M]国外液晶及应用,上海:科学技术情报研究所出版, 1971.
[70] .Tschierske, C. J. Mater. Chem, 1998, 8, 1485.
[71] .Collyer AA. Mater Sci Technol, 1989, 5, 309.
[72] .Sun T, Lin YG, Winter HH, Porter RS. Polymer, 1989, 30(7), 1257.
[73] .DeMeuse MT, Jaffe M. Polym Adv Technol, 1990, 1, 81.
[74] .Lin YG, Winter HH. Polym Engng Sci, 1992, 37, 773.
[75] .Koltzenbury S, Wolff D, Springer J. Polym. S ci Part A, 1998, 36, 2669.
[76]陆婉芳,张智勇,施耀曾.高等学校化学学报, 1995, 16, 719.
[77] .W. Weissflog, D. Demus. Crysi Res Techmol, 1984, 19, 55.
[78] .Vanmeter J P, Klanderman B H. J. Am. Chem. Soc, 1973, 95, 626.
[79] .Joo, S. H, Yun, Y. K, Jin, J. I. Kim, D. C, Zin, W. C. Macromolecules. 2000, 33, 6704.
[80]荣国斌,马汝建.液晶与显示, 1997, 12(30), 167.
[81]张智勇,莫小曼,陆婉芳,施耀曾.应用化学, 2003, 20(1), 59.
[82]张淑媛,朱鑫,刘萃红,王鹏飞.郑州大学学报(理学版), 2006, 38(1), 79.
[83]沈宁,高嫒嫒.合成化学, 2006 ,10(3), 228.
[84]李辉容,胡平,汪必琴,赵可清.四川师范大学学报(自然科学版), 2007, 30(2), 228.
[85]谢旈章. [M]液晶物理学,北京:科学出版社, 1998.
[86]郑安呐,陈建定,吴叙勤.自然杂志, 1991, 14(7), 512.
[1] .C.E.Sroog. Progr Polym Sci, 1991, 16(4), 561.
[2]程晖,何尚锦,张保龙.热固性树脂, 1999, 1, 16.
[3] .Micco G, Giamberini M, Amendola E, Carfagna C, Astarita G. Ind Eng Chem Re, 1997, 36, 2976.
[4] .Chun-Fang Li, Dong-Xiang Li, Sheng-Yu Feng. Polym Int, 2005, (54), 1041.
[5]杨山跃,赵美法.化工科技市场, 2005, (12), 33.
[6] .Shigeru Tsuruya, Yasushi Kishikawa, Ryozo Tanaka. Journal of Catalysis, 1977, 49(3), 254.
[7] .Mieke Huisman, Iryna A.Koval, Patrick Gamez, Jan Reedijk. Inorganica Chimica Acta, 2006, 359(6), 1786.
[8]任少平,吕满庚,凌有道. [ P]CN1660739, 2005, 08.
[9] .LI Xianming , DING Yunjie , JIAO Guiping , PAN Zhendong , JIANG Dahao, LIN Liwu. Chinese Journal of Catalysis, 2005, 26(4), 265.
[10] .Wariishi Hiroyuki, Kondo Akihiro, Nishihashi Shuji. [P]JP2008081449, 2008, 04.
[11] .Ishiyama Fumihiko, Kondo Akihiro, Tobisawa Takeshi, Murata Hideyuki, Aoki Toru. [P]JP2008081450, 2008, 04.
[12] .Kokai Tokkyo Koho. [P] Jpn.2008081449, 2008, 10.
[13] .Kokai Tokkyo Koho. [P] Jpn.2008081450, 2008, 10.
[14] Sagar Sharma, Nilotpal Barooah, Jubaraj B.Baruah. Journal of Molecular Catalysis A Chemical, 2005, 229, 171.
[15] .Bo Xiao, Hongwei Hou, Yaoting. Journal of Organometallic Chemistry, 2007, 692, 2014.
[16]朱杰,孟祥光,臧蓉蓉,陈民助.催化学报, 2005, 26(4), 317.
[17] .Anna M.Schuitema, Peternity G Aubel, Iryna A. Inorganica Chimica Acta , 2003, 355 (20), 374.
[18]凌有道,吕满庚,任少平. [P] CN 1706782, 2005, 12.
[19] W. L. Carrick, G. L. Karapinka, G. T. Kwinatkowski. The Journal of Organic Chemistry, 1969, (34), 2388.
[20] Christophe Boldron, Guillem Aromi, Ger Challa. Chemical Communications (Cambridge, United Kingdom), 2005, (46), 5808.
[21] .Mohamed Sarakha, Michele Bolte. Journal of Photobiology A: Chemistry, 1996, 97(1), 87.
[22] .Hay A S, Blanchard H S, Endres G F , Eustance J W. J Am Chem Soc, 1959, 81 (23), 6335.
[23]郭卫红,沈学宁,王彬芳,黄发荣.功能高分子学报, 2004, 17(2), 303.
[24]朱金华,申屠宝卿.化工生产与技术, 2007, 14(2), 32.
[1]蔡红莉,那辉.高等学校化学学报, 2006, 27(2), 372.
[2]律微波,李金辉.山东科学, 2007, 20(3), 76.
[3]李莉,张鹏云,李春新,刘云利.热固性树脂, 2006, 21(6), 18.
[4]杨瑞芹,张大洋,赵鸣玉,吕成学.热固性树脂, 1997, (3), 17.
[5]王睦铿.化工新型材料, 1996, (6), 36.
[6]蔡智奇,孙建中,任华,赵骞,周其云,徐军龙.高校化学工程学报, 2009, 23(3), 510.
[7]张毅,王久芬,韩亮.高分子材料科学与工程, 2004, 20(6), 80.
[8] Cai Zhiqi, Sun Jianzhong, Wang Daodeng, Zhou QiYun. J Polym Sci: Part A: Polym Chem, 2007, 45, 3922.
[9] .Hagen E L. Plast Technol, 1978, 24(10), 94.
[10]刘凉冰.弹性体, 1999, 9(3), 41.
[11] .Palmer M. Plast Technol, 1977, 23(11), 93.
[12]魏建国,庞喜刚.聚氨酯工业, 1997, 12(4), 36.
[13]刘少兵,赵彦生,贾林才,郝解玲,孙奉瑞,邹鹏.化工中间体, 2006, (2), 21.
[14]张少钢,吴石良,林仪智,叶军明.精细化工, 2001, 18(12), 741.
[15]陈启明,陈金芳,张良均,陈加玉,尹步云.化学与生物工程, 2005, (11), 20.
[16] .Brennan, Michael E. [P] US.4500655, 1985.
[17]张有明,李攀,张鹏云,刘志铭,魏太保.化工新型材料, 2010, 38(2), 115.
[18]曹文君.浙江化工, 1999, 30(4), 9.
[19]李斌,席海涛,孙小强.化学试剂, 2003, (1), 29.
[20]王建华,邵景景,任国安.化学试剂, 1994, (6), 371.
[21]崔晓静,刘承美,程小菊.精细石油化工, 2003, (2), 42.
[1] .Zhang Chunling, Na Hui. Chemical Research In Chinese Universities, 2004, (25), 1756.
[2] .Sue H J, Earls J D, Hefner Jr R E. Polymer, 1998, 39(20), 4707.
[3] .Zhang Chunling, Na Hui, Liu Chenguang. Thermoseting Resin, 2002, 17(1), 1.
[4]谭怀山,欧雄燕,代堂军,徐伟箭,熊远钦.化工新型材料, 2008, 11(36), 49.
[5]陈平,刘胜平. [M]环氧树脂,北京:化学工业出版社, 1999.
[6] .Yokouchi Hitoshi, Ohashi Hiroyuk. [P]JP09216937, 2006.
[7]吕长利,崔占臣,赵冬雪.高等学校化学学报, 2001, 22(11), 1924.
[8]石宁.热固性树脂, 2000, 15(2), 30.
[9] .Ching Hsuan Lin, Jung Min Huang, Chun-Shan Wang. Polymer, 2002, 43(10), 2959.
[10] .ZHI-QI CAI, JIANZHONG SUN, DAODENG WANG, Qiyun Zhou. Journal of Polymer Science: Part A: Polymer Chemistry, 2007, (45), 3922.
[11] .Jun Yeob Lee, Jyongsik Jang, Seung Sang Hwang, Kwang Ung Kim. Polymer, 1998, 24(39), 6121.
[12]唐正贵,张车文,乐以伦.化学试剂, 1994, 16(2), 107.
[13]黄启谷,张海良,王霞瑜.湘潭大学自然科学学报, 1997, 19(1), 60.
[14]唐正贵,张车文,乐以伦.合成化学, 1993, 1(4), 364.
[15]阳明山,何杰,李林楷,徐文玉.现代塑料加工应用, 2008, 20(4), 53.
[16]任少平,吕满庚,凌有道,郑一泉. [P]CN1733745A, 2006, 02.
[17]牛古丹,李东颖,吴宝华.韶关学院学报·自然科学, 2006, 27(12), 66.
[18]王春颖,孙皓,陈晓婷,唐旭东.天津科技大学学报, 2007, 22(2), 29.
[19]蔡智奇,孙建中,任华,赵骞,周其云,徐军龙.高校化学工程学报, 2009, 23(3), 510.
[20]黄启谷,贺小华,王霞瑜.化工新型材料, 1997, (4), 34.
[21]李莉,张鹏云,李春新,刘云利.热固性树脂, 2006, 21(6), 18.
[22]张春玲,那辉,刘晨光,葛振宇.热固性树脂, 2002, 17(1), 1.
[23]棘云飞,李永强.中国环氧树脂应用技术学会“第十三次全国环氧树脂应用技术学术交流会”论文集, 2009, 10, 149.
[24]袁慧五,饶秋华.热固性树脂, 2007, 22(5), 1.
[25] .D J Broer, J Lub, G N Mol. Macromolecules, 1993, 26, 1244.
[26]张晓娜,高俊刚,刘晓丹,赵洪池.化学研究与应用, 2008, 20(9), 1133.
[27]周博,刘国栋,高俊刚.塑料工业, 2008, 36(7), 16.
[28]陈梦雪,胡国贞.化工新型材料, 2007, 20(9), 20.
[1]王雨来.福建轻纺, 2001, 4, 24.
[2] .Koltzenbury S, Wolff D, Springer J. Polym. Sci , Part A, 1998, 36, 2669.
[3]陆婉芳,张智勇,施耀曾.高等学校化学学报, 1995, 16, 719.
[4] .Gray, G. W. Mol. Cryst. Liq, 1973, 21, 161.
[5] .Yoshida. A. [P]JP 6100291, 1986.
[6] .Miyaji Y, Takeshita A Y, Kiyonaga B. [P]JP 6121186, 1986.
[7]赵慧敏,房威,王良御.清华大学学报, 1987, 27(6), 57.
[8]赵敏,蒯乃功.华东理工大学学报(自然科学版), 1996, 22(2), 217.
[9] .Hoshino N, Matsuoka Y, Okamoto K, Yamagishi A. J. Am. Chem. Soc, 2003, 125, 1718.
[10] .Choi E, Ahn J, Chien L. Macromolecules, 2004, 37, 71.
[11] .Lehmann M, Gearba R I, Kochmichel H J. Chem Mater, 2004, 16, 374.
[12] .Bahadu B. Liq Cryst, 1984, 109, 30.
[13]李洋,聂王焰,应加银,周艺峰.合成化学, 2008, 5(16), 574.
[14] .Jun Yeob Lee, Jyongsik Jang, Seung Sang Hwang, Soon Man Hong, Kwang Ung Kim. Polymer, 1998, 39(24), 6121.
[15]郑敏燕,安忠维.应用化学, 2007, 24(4), 396.
[16]王良御,廖松生. [M]液晶化学,北京:科学出版社, 1988.
[17]汪必琴,余文浩,赵可清,胡平.化学研究与应用, 2007, 11(19), 1215.
[18]李辉容,胡平,汪必琴,赵可清.四川师范大学学报(自然科学版), 2007,30(2), 223.
[19] .Demus J D. [M]Texture of Liquid Crystals. V. C. Weinheim, New York, 1978.
[20]沈金平,章于川,范程士,张彩云,李国喜.液晶与显示, 2006, 21(1), 11.
[21]刘秀英,王玉阳.化学研究与应用, 2010, 22(3), 347.
[22]董德文,韩平,倪玉山,丁孟贤,韩伟.应用化学, 1996, 13(2), 79.
[23]袁柱良,于宗强,夏安英,谭松庭.液晶与显示, 2006, 21(4), 303.
[24]连彦青,杨京伟,高彦芳,申胜军,周其庠,刘德山.清华大学学报(自然科学版), 1997, 37(12), 37.
[25]王华芹,和亚宁,连彦青,王晓工.高分子学报, 2008, (3), 237.
[26]刘鲁梅,张宝砚,刘作军,张璐.高分子学报, 2001, 16(3), 198.
[27]吴兵,范程士,章于川.液晶与显示, 2007, 22(1), 21.
[28]唐斯甫,王志玲,徐晓辉,李自法,朱卫国,侯红卫,张淑媛.郑州大学学报:理学版, 2003, 35(4), 77.
[29]魏爱卿,郑世军.郑州大学学报:理学版, 2005, 37(3), 88.
[30]何可可,张晓静,李自法,张淑媛,郑世军,杨振华,郭凯,周其凤.高等学校化学学报, 2002, (10), 2000.
[31]刘铸晋. [M]液晶的性质和应用,上海:上海科学技术文献出版社, 1981.
[2]王雨来.新技术新产品新工艺, 2001, (4), 24.
[3] .Shigeru Tsuruya, Yasushi Kishikawa, Ryozo Tanaka. Journal of Catalysis, 1977, 49, 254.
[4] .Anna M Schuitema, Peternity G Aubel, Iryna A. Inorganica Chimica Acta, 2003, 355, 374.
[5] .Mieke Huisman, Iryna A Koval, Patrick Gamez, Jan Reedijk. Inorganica Chimica Acta, 2006, 359, 1786.
[6]蒋忠良,汪正发,马东旭.同济大学学报, 2002, 30(7), 904.
[7] Sagar Sharma, Nilotpal Barooah, Jubaraj Baruah. Journal of Molecular Catalysis A Chemical, 2005, 229, 171.
[8] .Bo Xiao, Hongwei Hou, Yaoting. Journal of Organometallic Chemistry, 2007, 692, 2014.
[9]朱杰,孟祥光,臧蓉蓉,陈民助.催化学报, 2005, 26(4), 317.
[10] .Inui Naoki, Kikuchi Taketoshi, Tanaka Shinya. [P] WO9946227, 1999, 09.
[11] .W. L. Carrick, G. L. Karapinka, G. T. Kwinatkowski. The Journal of Organic Chemistry , 1969, (34), 2388.
[12]凌有道,吕满庚,任少平. [P] CN 1706782, 2005, 12.
[13]刘群,申屠宝卿,翁志学.高校化学工程学报, 2008, 22(5), 906.
[14] Christophe Boldron, Guillem Aromi, Ger Challa. Chemical Communications(Cambridge, United Kingdom), 2005, (46), 5808.
[15] .Mohamed Sarakha, Michele Bolte. Journal of Photobiology A:Chemistry, 1996, (97), 87.
[16] .C.E.Sroog. Progr Polym Sci, 1991, 16(4), 561.
[17]程晖,何尚锦,张保龙.热固性树脂, 1999, 1, 16.
[18] .Chun-Fang Li, Dong-Xiang Li, Sheng-Yu Feng. Polym Int, 2005, (54), 1041.
[19]汪多仁. [M]溶剂与专用化学品生产配方和合成工艺,北京:科学技术文献出版社, 2003.
[20]刘凉冰.弹性体, 1999, 9(3), 41.
[21] .Brennan, Michael E. [P] US.4500655, 1985, 2.
[22]周建. [P] 200810010725, 2008, 8.
[23] .Harris Eugene G. [P] US.4533759, 1985.
[24]范存良,杨忠保,单根林,奚军.石油化工, 1999, 28(4), 250.
[25]张少钢,吴石良,林仪智,叶军明.精细化工, 2001, 18(12), 741.
[26]孙冬兵,王树清,高崇.精细石油化工进展, 2008, 9(11), 24.
[27]李斌,席海涛,孙小强.化学试剂, 2003, 25(1), 29.
[28]崔晓静,刘承美,程晓菊.精细石油化工, 2003, (2), 42.
[29]蒋青,陈益钊,李聚才,李文藻,郁陵庄.化学试剂, 1993, 15(4), 246.
[30]张有明,李攀,张鹏云,刘志铭,魏太保.化工新型材料, 2010, 38(2), 115.
[31]陈平,刘胜平. [M]环氧树脂,北京:化学工业出版社, 1999.
[32]伍敏扬.化工新型材料, 1999, 27(3), 22.
[33]石宁.热固性树脂, 2000, 15(2), 30.
[34]陈立新,蓝立文,王汝敏.材料导报, 2000, 14(9), 41.
[35]左瑞霖,常鹏善,解云川,陈建平.高分子材料科学与工程, 2002, 18(4), 6.
[36]刘国栋,李卿,高俊刚,张留成.高分子材料科学与工程, 2008, 24(10), 12.
[37]李冰.化工技术与开发, 2009, 38(3), 29.
[38]刘伟昌,申胜军,刘德山.高分子通报, 1998, (3), 59.
[39] .Carfagna C, Amendola E, Gramberm M. J Mater Sci Let, 1994, 13, 126.
[40] .Carfagna C, Nicolaiai L, Amendola E. Journal of applied Polymer science, 1992, 44(8), 1465.
[41] .Sue H J, Earla J D , Hefner R E Jr. Journal of materials science, 1997, 32(15),4031.
[42]肖潇.科技资讯, 1998, (19), 11.
[43]吴良义.热固性树脂, 2000, 15(4), 21.
[44] .Roland G, Heinrich H, Hanns P M, DE 3622610(EP252358, USP 4764581), 1986.
[45]杨小王,陆绍荣,虞锦洪,吴兵.高分子材料科学与工程, 2008, 24(2), 39.
[46]刘伟昌,申胜军.清华大学学报(自然科学版), 1998, 38(12), 104.
[47]陈立新,王汝敏,蓝立文.玻璃钢/复合材料, 2000, 2, 28.
[48]液晶环氧树脂研究在国外取得新成果.摘自“中国化工信息网”.
[49] .Vyazo S, Mitite A, Sbirra N. Macromol Rapid Commun, 2003, 18(24), 1060.
[50] .Prakaipetch P, Veronica A, Marta G. Polymer, 2002, 43(3), 839.
[51]谢东.科技潮, 1998, (11) , 46.
[52]李帅,任培兵,仲锡军,段二红,赵地顺.河北化工, 2008, 9(31), 28.
[53] .F. Reinitzer. Montash Chem, 1888, 9, 421.
[54] .G. Friedel, Ann. Physique(Paris), 1922, 18, 273.
[55] .A. J. Bosman, E. E. Havinga. Phys. Rev, 1963, 129(4), 1593.
[56] .E.Bose. Z.Phys, 1909, 10, 230.
[57] .V.Grandjean. Z. Phys, 1911, 12, 1011.
[58]王良御,廖松生. [M]液晶化学,北京:科学出版社, 1988.
[59]汪朝阳.化工时刊, 2002, (11), 25.
[60]吴大诚,谢新光,徐建军. [M]高分子液晶,成都:四川教育出版社, 1988.
[61]郭强. [M]液晶显示应用技术,北京:电子工业出版社, 2000.
[62]杨柏梁.液晶与显示, 2000, 2(15) , 154.
[63]谈漫琪,丁学泉. [M]液晶知识,北京:科学普及出版社, 1984.
[64]张文志.科技信息, 2007, 19, 46.
[65]刘铸晋. [M]液晶的性质和应用,上海:科学技术文献出版社, 1981, 5.
[66]周其凤,王新久. [M]液晶高分子,北京:科学出版社, 1999.
[67]徐晓鹏,底楠.化工新型材料, 2006, 34(11) , 81.
[68]范程士.安徽大学研究生学位论文, 2005.
[69] . [M]国外液晶及应用,上海:科学技术情报研究所出版, 1971.
[70] .Tschierske, C. J. Mater. Chem, 1998, 8, 1485.
[71] .Collyer AA. Mater Sci Technol, 1989, 5, 309.
[72] .Sun T, Lin YG, Winter HH, Porter RS. Polymer, 1989, 30(7), 1257.
[73] .DeMeuse MT, Jaffe M. Polym Adv Technol, 1990, 1, 81.
[74] .Lin YG, Winter HH. Polym Engng Sci, 1992, 37, 773.
[75] .Koltzenbury S, Wolff D, Springer J. Polym. S ci Part A, 1998, 36, 2669.
[76]陆婉芳,张智勇,施耀曾.高等学校化学学报, 1995, 16, 719.
[77] .W. Weissflog, D. Demus. Crysi Res Techmol, 1984, 19, 55.
[78] .Vanmeter J P, Klanderman B H. J. Am. Chem. Soc, 1973, 95, 626.
[79] .Joo, S. H, Yun, Y. K, Jin, J. I. Kim, D. C, Zin, W. C. Macromolecules. 2000, 33, 6704.
[80]荣国斌,马汝建.液晶与显示, 1997, 12(30), 167.
[81]张智勇,莫小曼,陆婉芳,施耀曾.应用化学, 2003, 20(1), 59.
[82]张淑媛,朱鑫,刘萃红,王鹏飞.郑州大学学报(理学版), 2006, 38(1), 79.
[83]沈宁,高嫒嫒.合成化学, 2006 ,10(3), 228.
[84]李辉容,胡平,汪必琴,赵可清.四川师范大学学报(自然科学版), 2007, 30(2), 228.
[85]谢旈章. [M]液晶物理学,北京:科学出版社, 1998.
[86]郑安呐,陈建定,吴叙勤.自然杂志, 1991, 14(7), 512.
[1] .C.E.Sroog. Progr Polym Sci, 1991, 16(4), 561.
[2]程晖,何尚锦,张保龙.热固性树脂, 1999, 1, 16.
[3] .Micco G, Giamberini M, Amendola E, Carfagna C, Astarita G. Ind Eng Chem Re, 1997, 36, 2976.
[4] .Chun-Fang Li, Dong-Xiang Li, Sheng-Yu Feng. Polym Int, 2005, (54), 1041.
[5]杨山跃,赵美法.化工科技市场, 2005, (12), 33.
[6] .Shigeru Tsuruya, Yasushi Kishikawa, Ryozo Tanaka. Journal of Catalysis, 1977, 49(3), 254.
[7] .Mieke Huisman, Iryna A.Koval, Patrick Gamez, Jan Reedijk. Inorganica Chimica Acta, 2006, 359(6), 1786.
[8]任少平,吕满庚,凌有道. [ P]CN1660739, 2005, 08.
[9] .LI Xianming , DING Yunjie , JIAO Guiping , PAN Zhendong , JIANG Dahao, LIN Liwu. Chinese Journal of Catalysis, 2005, 26(4), 265.
[10] .Wariishi Hiroyuki, Kondo Akihiro, Nishihashi Shuji. [P]JP2008081449, 2008, 04.
[11] .Ishiyama Fumihiko, Kondo Akihiro, Tobisawa Takeshi, Murata Hideyuki, Aoki Toru. [P]JP2008081450, 2008, 04.
[12] .Kokai Tokkyo Koho. [P] Jpn.2008081449, 2008, 10.
[13] .Kokai Tokkyo Koho. [P] Jpn.2008081450, 2008, 10.
[14] Sagar Sharma, Nilotpal Barooah, Jubaraj B.Baruah. Journal of Molecular Catalysis A Chemical, 2005, 229, 171.
[15] .Bo Xiao, Hongwei Hou, Yaoting. Journal of Organometallic Chemistry, 2007, 692, 2014.
[16]朱杰,孟祥光,臧蓉蓉,陈民助.催化学报, 2005, 26(4), 317.
[17] .Anna M.Schuitema, Peternity G Aubel, Iryna A. Inorganica Chimica Acta , 2003, 355 (20), 374.
[18]凌有道,吕满庚,任少平. [P] CN 1706782, 2005, 12.
[19] W. L. Carrick, G. L. Karapinka, G. T. Kwinatkowski. The Journal of Organic Chemistry, 1969, (34), 2388.
[20] Christophe Boldron, Guillem Aromi, Ger Challa. Chemical Communications (Cambridge, United Kingdom), 2005, (46), 5808.
[21] .Mohamed Sarakha, Michele Bolte. Journal of Photobiology A: Chemistry, 1996, 97(1), 87.
[22] .Hay A S, Blanchard H S, Endres G F , Eustance J W. J Am Chem Soc, 1959, 81 (23), 6335.
[23]郭卫红,沈学宁,王彬芳,黄发荣.功能高分子学报, 2004, 17(2), 303.
[24]朱金华,申屠宝卿.化工生产与技术, 2007, 14(2), 32.
[1]蔡红莉,那辉.高等学校化学学报, 2006, 27(2), 372.
[2]律微波,李金辉.山东科学, 2007, 20(3), 76.
[3]李莉,张鹏云,李春新,刘云利.热固性树脂, 2006, 21(6), 18.
[4]杨瑞芹,张大洋,赵鸣玉,吕成学.热固性树脂, 1997, (3), 17.
[5]王睦铿.化工新型材料, 1996, (6), 36.
[6]蔡智奇,孙建中,任华,赵骞,周其云,徐军龙.高校化学工程学报, 2009, 23(3), 510.
[7]张毅,王久芬,韩亮.高分子材料科学与工程, 2004, 20(6), 80.
[8] Cai Zhiqi, Sun Jianzhong, Wang Daodeng, Zhou QiYun. J Polym Sci: Part A: Polym Chem, 2007, 45, 3922.
[9] .Hagen E L. Plast Technol, 1978, 24(10), 94.
[10]刘凉冰.弹性体, 1999, 9(3), 41.
[11] .Palmer M. Plast Technol, 1977, 23(11), 93.
[12]魏建国,庞喜刚.聚氨酯工业, 1997, 12(4), 36.
[13]刘少兵,赵彦生,贾林才,郝解玲,孙奉瑞,邹鹏.化工中间体, 2006, (2), 21.
[14]张少钢,吴石良,林仪智,叶军明.精细化工, 2001, 18(12), 741.
[15]陈启明,陈金芳,张良均,陈加玉,尹步云.化学与生物工程, 2005, (11), 20.
[16] .Brennan, Michael E. [P] US.4500655, 1985.
[17]张有明,李攀,张鹏云,刘志铭,魏太保.化工新型材料, 2010, 38(2), 115.
[18]曹文君.浙江化工, 1999, 30(4), 9.
[19]李斌,席海涛,孙小强.化学试剂, 2003, (1), 29.
[20]王建华,邵景景,任国安.化学试剂, 1994, (6), 371.
[21]崔晓静,刘承美,程小菊.精细石油化工, 2003, (2), 42.
[1] .Zhang Chunling, Na Hui. Chemical Research In Chinese Universities, 2004, (25), 1756.
[2] .Sue H J, Earls J D, Hefner Jr R E. Polymer, 1998, 39(20), 4707.
[3] .Zhang Chunling, Na Hui, Liu Chenguang. Thermoseting Resin, 2002, 17(1), 1.
[4]谭怀山,欧雄燕,代堂军,徐伟箭,熊远钦.化工新型材料, 2008, 11(36), 49.
[5]陈平,刘胜平. [M]环氧树脂,北京:化学工业出版社, 1999.
[6] .Yokouchi Hitoshi, Ohashi Hiroyuk. [P]JP09216937, 2006.
[7]吕长利,崔占臣,赵冬雪.高等学校化学学报, 2001, 22(11), 1924.
[8]石宁.热固性树脂, 2000, 15(2), 30.
[9] .Ching Hsuan Lin, Jung Min Huang, Chun-Shan Wang. Polymer, 2002, 43(10), 2959.
[10] .ZHI-QI CAI, JIANZHONG SUN, DAODENG WANG, Qiyun Zhou. Journal of Polymer Science: Part A: Polymer Chemistry, 2007, (45), 3922.
[11] .Jun Yeob Lee, Jyongsik Jang, Seung Sang Hwang, Kwang Ung Kim. Polymer, 1998, 24(39), 6121.
[12]唐正贵,张车文,乐以伦.化学试剂, 1994, 16(2), 107.
[13]黄启谷,张海良,王霞瑜.湘潭大学自然科学学报, 1997, 19(1), 60.
[14]唐正贵,张车文,乐以伦.合成化学, 1993, 1(4), 364.
[15]阳明山,何杰,李林楷,徐文玉.现代塑料加工应用, 2008, 20(4), 53.
[16]任少平,吕满庚,凌有道,郑一泉. [P]CN1733745A, 2006, 02.
[17]牛古丹,李东颖,吴宝华.韶关学院学报·自然科学, 2006, 27(12), 66.
[18]王春颖,孙皓,陈晓婷,唐旭东.天津科技大学学报, 2007, 22(2), 29.
[19]蔡智奇,孙建中,任华,赵骞,周其云,徐军龙.高校化学工程学报, 2009, 23(3), 510.
[20]黄启谷,贺小华,王霞瑜.化工新型材料, 1997, (4), 34.
[21]李莉,张鹏云,李春新,刘云利.热固性树脂, 2006, 21(6), 18.
[22]张春玲,那辉,刘晨光,葛振宇.热固性树脂, 2002, 17(1), 1.
[23]棘云飞,李永强.中国环氧树脂应用技术学会“第十三次全国环氧树脂应用技术学术交流会”论文集, 2009, 10, 149.
[24]袁慧五,饶秋华.热固性树脂, 2007, 22(5), 1.
[25] .D J Broer, J Lub, G N Mol. Macromolecules, 1993, 26, 1244.
[26]张晓娜,高俊刚,刘晓丹,赵洪池.化学研究与应用, 2008, 20(9), 1133.
[27]周博,刘国栋,高俊刚.塑料工业, 2008, 36(7), 16.
[28]陈梦雪,胡国贞.化工新型材料, 2007, 20(9), 20.
[1]王雨来.福建轻纺, 2001, 4, 24.
[2] .Koltzenbury S, Wolff D, Springer J. Polym. Sci , Part A, 1998, 36, 2669.
[3]陆婉芳,张智勇,施耀曾.高等学校化学学报, 1995, 16, 719.
[4] .Gray, G. W. Mol. Cryst. Liq, 1973, 21, 161.
[5] .Yoshida. A. [P]JP 6100291, 1986.
[6] .Miyaji Y, Takeshita A Y, Kiyonaga B. [P]JP 6121186, 1986.
[7]赵慧敏,房威,王良御.清华大学学报, 1987, 27(6), 57.
[8]赵敏,蒯乃功.华东理工大学学报(自然科学版), 1996, 22(2), 217.
[9] .Hoshino N, Matsuoka Y, Okamoto K, Yamagishi A. J. Am. Chem. Soc, 2003, 125, 1718.
[10] .Choi E, Ahn J, Chien L. Macromolecules, 2004, 37, 71.
[11] .Lehmann M, Gearba R I, Kochmichel H J. Chem Mater, 2004, 16, 374.
[12] .Bahadu B. Liq Cryst, 1984, 109, 30.
[13]李洋,聂王焰,应加银,周艺峰.合成化学, 2008, 5(16), 574.
[14] .Jun Yeob Lee, Jyongsik Jang, Seung Sang Hwang, Soon Man Hong, Kwang Ung Kim. Polymer, 1998, 39(24), 6121.
[15]郑敏燕,安忠维.应用化学, 2007, 24(4), 396.
[16]王良御,廖松生. [M]液晶化学,北京:科学出版社, 1988.
[17]汪必琴,余文浩,赵可清,胡平.化学研究与应用, 2007, 11(19), 1215.
[18]李辉容,胡平,汪必琴,赵可清.四川师范大学学报(自然科学版), 2007,30(2), 223.
[19] .Demus J D. [M]Texture of Liquid Crystals. V. C. Weinheim, New York, 1978.
[20]沈金平,章于川,范程士,张彩云,李国喜.液晶与显示, 2006, 21(1), 11.
[21]刘秀英,王玉阳.化学研究与应用, 2010, 22(3), 347.
[22]董德文,韩平,倪玉山,丁孟贤,韩伟.应用化学, 1996, 13(2), 79.
[23]袁柱良,于宗强,夏安英,谭松庭.液晶与显示, 2006, 21(4), 303.
[24]连彦青,杨京伟,高彦芳,申胜军,周其庠,刘德山.清华大学学报(自然科学版), 1997, 37(12), 37.
[25]王华芹,和亚宁,连彦青,王晓工.高分子学报, 2008, (3), 237.
[26]刘鲁梅,张宝砚,刘作军,张璐.高分子学报, 2001, 16(3), 198.
[27]吴兵,范程士,章于川.液晶与显示, 2007, 22(1), 21.
[28]唐斯甫,王志玲,徐晓辉,李自法,朱卫国,侯红卫,张淑媛.郑州大学学报:理学版, 2003, 35(4), 77.
[29]魏爱卿,郑世军.郑州大学学报:理学版, 2005, 37(3), 88.
[30]何可可,张晓静,李自法,张淑媛,郑世军,杨振华,郭凯,周其凤.高等学校化学学报, 2002, (10), 2000.
[31]刘铸晋. [M]液晶的性质和应用,上海:上海科学技术文献出版社, 1981.