含液晶基元的聚合物的制备
摘要
本文预设计具有较大空间结构的含液晶基元的疏水性单体,并通过ATRP聚合法和巯基链转移支化聚合法获得含液晶基元的聚合物,并对其性能进行了测试。
一、设计并合成了具较大空间结构的咔唑基苯乙烯类可聚合单体CCS、ATRP大分子引发剂MPEG-Br,及高效ATRP配体Me6[14]aneN4,通过ATRP法合成了新型双亲嵌段聚合物MPEG-b-PCCS。对各反应过程及产物进行了红外、核磁、质谱、凝胶色谱法(GPC)等跟踪测试。
二、通过对氯甲基苯乙烯与硫代硫酸钠盐水溶液的Bunte盐反应,设计合成同时含有潜伏性巯基和可聚合双键的苯乙烯类单体SATCS;以SATCS为支化单体、AIBN为引发剂、DMSO为聚合溶剂、考察该单体均聚条件下及与苯乙烯共聚下的聚合机制,从而建立一种新型支化聚合法――巯基链转移支化聚合法。并利用红外、核磁、凝胶色谱法(GPC)/激光光散射法(LS)/示差粘度(DV)三检测技术表征所得聚合物。
三、利用巯基链转移支化聚合法设计、合成了一种咔唑基苯乙烯类可聚合单体CCS的支化聚合物Branched PCCS。通过XRD测试来观察Branched PCCS做规整排列的能力。
In this paper, a large space hydrophobic liquid crystal contained monomer was designed and synthesized, which was used to synthesis liquid crystal pendent containing polymers through ATRP and Mercapto Chain-Transfer Polymerization (MCTP) and the properties of these polymers were detected.
First of all, the carbazole pendent containing styrene monomer (CCS), ATRP macroinitiator MPEG-Br, and the efficient ATRP ligand Me6[14]aneN4 were designed and synthesized, which were used to synthesis of novel amphiphilic block polymer MPEG-b-PCCS by ATRP. The monomer and polymers were characterized by FTIR, 1H-NMR, MS and GPC.
Secondly, the sodium S-alkylthiosulfuric-containing styrene monomer (SATCS) was designed and synthesized through the Bunte salt reaction, we use SATCS as monomer , AIBN as initiator to prepare Branched PSATCS in DMSO solvent and we also use SATCS as branched monomer together with styrene (St) and AIBN to prepare branched polystyrene (BPS) in DMSO solvent. These polymers were characterized by FTIR, 1H-NMR and multiple detectors GPC/LS/DV in THF at 30 oC. And we call this new method Mercapto Chain-Transfer Polymerization (MCTP).
Finally, we use carbazole-unite-containing styrene monomer (CCS) as monomer to prepare a carbazole-unit-containing branched polymer by MCTP which was characterized by XRD.
一、设计并合成了具较大空间结构的咔唑基苯乙烯类可聚合单体CCS、ATRP大分子引发剂MPEG-Br,及高效ATRP配体Me6[14]aneN4,通过ATRP法合成了新型双亲嵌段聚合物MPEG-b-PCCS。对各反应过程及产物进行了红外、核磁、质谱、凝胶色谱法(GPC)等跟踪测试。
二、通过对氯甲基苯乙烯与硫代硫酸钠盐水溶液的Bunte盐反应,设计合成同时含有潜伏性巯基和可聚合双键的苯乙烯类单体SATCS;以SATCS为支化单体、AIBN为引发剂、DMSO为聚合溶剂、考察该单体均聚条件下及与苯乙烯共聚下的聚合机制,从而建立一种新型支化聚合法――巯基链转移支化聚合法。并利用红外、核磁、凝胶色谱法(GPC)/激光光散射法(LS)/示差粘度(DV)三检测技术表征所得聚合物。
三、利用巯基链转移支化聚合法设计、合成了一种咔唑基苯乙烯类可聚合单体CCS的支化聚合物Branched PCCS。通过XRD测试来观察Branched PCCS做规整排列的能力。
In this paper, a large space hydrophobic liquid crystal contained monomer was designed and synthesized, which was used to synthesis liquid crystal pendent containing polymers through ATRP and Mercapto Chain-Transfer Polymerization (MCTP) and the properties of these polymers were detected.
First of all, the carbazole pendent containing styrene monomer (CCS), ATRP macroinitiator MPEG-Br, and the efficient ATRP ligand Me6[14]aneN4 were designed and synthesized, which were used to synthesis of novel amphiphilic block polymer MPEG-b-PCCS by ATRP. The monomer and polymers were characterized by FTIR, 1H-NMR, MS and GPC.
Secondly, the sodium S-alkylthiosulfuric-containing styrene monomer (SATCS) was designed and synthesized through the Bunte salt reaction, we use SATCS as monomer , AIBN as initiator to prepare Branched PSATCS in DMSO solvent and we also use SATCS as branched monomer together with styrene (St) and AIBN to prepare branched polystyrene (BPS) in DMSO solvent. These polymers were characterized by FTIR, 1H-NMR and multiple detectors GPC/LS/DV in THF at 30 oC. And we call this new method Mercapto Chain-Transfer Polymerization (MCTP).
Finally, we use carbazole-unite-containing styrene monomer (CCS) as monomer to prepare a carbazole-unit-containing branched polymer by MCTP which was characterized by XRD.
引文
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[2] Yu K, Eisenberg A. Bilayer Morphologies of Self-Assembled Crew-Cut Aggregates of Amphiphilic PS-b-PEO Diblock Copolymers in Solution [J]. Macromolecules, 1998, 31: 3509-3518
[3] Jenekhe S A, Chen X L. Self-asembly of ordered microporous materials from rod-coil block copolymers [J]. Science, 1999, 283: 372-375
[4] Vriezema D M, Hoogboom J, Velonia K, Takazawa K, Christiane P C M, Maan J C, Rowan A E, Nolte R J M. Vesicles and polymerized vesicles from thiophene-containing rod-coil block copolymers [J]. Angew Chem Int Ed, 2003, 42: 772-776
[5] Raez J, Manners L, Winnik M A. Nanotubes from the self-assembly of asymmetric Crystal-coil poly(ferrocenylsilane-siloxane) block copolymers [J]. J Am Chem Soc, 2002, 124: 10381-10395
[6] Zhou Q. F., Li H. M., Feng X. D.. Synthesis of liquid-crystal polyacrylates with laterally substituted mesogens [J]. Macromolecules, 1987, 20: 233-234
[7] Lee M., Cho B. K., Zin W. C.. Supramolecular Structures from Rod-Coil Block Copolymers [J]. Chem. Rev., 2001, 101(12): 3869-3892
[8] Chen J. T., Thomas E. L., Ober C. K.,Hwang S. S.. Zigzag Morphology of a Poly(styrene-b-hexyl isocyanate) Rod-Coil Block Copolymer [J]. Macromolecules,1995, 28(5): 1688-1697
[9] Yi Y., Fan X. H., Wan X. H., Li L., et al. ABA Type Triblock Copolymer Based on Mesogen-Jacketed Liquid Crystal Polymer: Design, Synthesis, and Potential as Thermoplastic Elastomer [J]. Macromolecules, 2004, 37(20): 7610-7618
[10]赵辉,罗云军,宋海香.超支化聚合物研究进展(II)超支化聚合物的合成[J].热固性树脂. 2004, 19(5):31-34
[11]谭惠民,罗运军.超支化聚合物[J].北京:化学工业出版社, 2004.
[12] C. R. Yates, W. Hayes. Synthesis and applications of hyperbranched polymers [J]. European Polymer Journal, 2004, 40: 1257-1281
[13] Kuo-Chung Chenga, Trong-Ming Donb, Wenjeng Guoa, Tsu-Hwang Chuang. Kinetic model of hyperbranched polymers formed by the polymerization of AB2 monomer with a substitution effect [J].Polymer, 2002,43: 6315-6322
[14] Hawker. C. J, Frechet. J. M. Preparation of hyperbranched and starpolymers by Living, self-condensing free radical polymerization [J]. Am ChemSoc, 1995, 117(43)
[15]赵辉,罗云军,宋海香.超支化聚合物研究进展(II)超支化聚合物的合成[J].热固性树脂. 2004, 19(5):10763-10764
[16]赵辉,罗云军,宋海香.超支化聚合物研究进展(II)超支化聚合物的合成[J].热固性树脂. 2004, 19(5):31-34
[17] Deyue Yan, Axel H. E. Muller, Krzysztof Matyjaszewski. Molecular Parameters of Hyperbranched Polymers Made by Self-Condensing Vinyl Polymerization. 2. Degree of Branching [J]. Macromolecules, 1997, 30(23): 7024-7033
[18] Mourey T H, Turner S R. Unique behavior of dendritic macromolecules: intrinsic viscosity of polyether dendrimers [J]. Macromolecules, 1992, 25: 2401
[19] Tuner S R, Voit B I. All aromatic hyperbranched polyesters with phenol and acetate end groups: synthesis and characterization [J].Macromolecules, 1996, 25: 2401
[20] Seiler M, Kohler D, Arlt W. Hyperbranched polymers: new selective solvents for extractive distillation and solvent extraction [J]. Purif Technol, 2003, 30: 179
[21] Kim Y H, Webster O W. Water soluble hyperbranched polyphenylene:“a unimolecular micelle?”[J]. J Am Chem Soc, 1990, 112: 4592
[22]赵宝辉,巴信武,侯文龙,等.超支化聚(酰胺-酯)/聚氯乙烯共混体系流变性能及其力学性能研究[J].高分子材料科学与工程, 2003, 19(2): 157-160
[23]张晓龙,唐黎明,邱腾,付永柱,刘德山.新型芳香型超支化聚酯的合成与应用研究[J].高等学校化学学报, 2001, 22(10): 1761-1763
[24]寇玉霞,童身毅.超支化聚合物合成及其端基改性[J].上海涂料, 2004, 42(2):703-711.
[25]夏敏,罗运军,李国平,张文栓.超支化环氧化合物的合成与应用[J].工程塑料应用, 2006, 34(5): 69-72
[26]寿崇琪,张志良,邢希学,康杰分.超支化聚酯涂层毛细管电泳柱的制备及评价[J],化学通报, 2006, (1): 230-233
[27]寿崇琪,张志良,周长利,赵春宾,李关宾,陈立仁.超支化聚合物化学键合毛细管电泳柱的制备及其对蛋白质的分离行为[J],色谱, 2004, 22(3): 273-276
[28]寿崇琪,张志良,邢希学,康杰分,欧庆瑜.超支化聚合物化学键合毛细管电泳柱的制备及碱性蛋白质的分离[J],分析化学研究简报, 2006, 34(9): 1287-1290
[29]孙宁,董磊,程兰兰,任碧野,童真.超支化聚合物在功能材料中的应用[J].化工时刊, 2006, 20(8): 61-64
[30] Van Hest J C M, Delnoye D A P, Baars M W P L, etc. Polystyrene-poly(propylene imine) dendrime: Synthesis,characterization, and association behavior of a new class of amphiphiles [J]. Chem Eur J, 1996, 2: 1616-1626
[31] Yan D Y, Zhou Y E, Hou J. Supramolecular self-assembly of macroscopic tubes [J]. Science, 2004, 303: 65-67
[32]万涛,王跃川.超支化大分子的最新应用进展[J].弹性体, 2004, 14(4): 59-61
[33] Liu. H, Jiang. A, Guo. J, Uhrich. K. E. Synthesis and characterization of Amphiphilic polymer systems [J]. Journal of Polymer Science, Part A: PolymerChemistry, 1999, 37(6): 15-19
[34] Bronstein L, Krarner E, Antonietti M, etc. Successive use of amphiphilie block copolymers as nanoreactions and templates: Preparation of porous silica with metal nanoparticles [J]. Chem. Mater, 1999, 11(6): 1402-1405
[35] Moffitt M, Eisenberg A. Size Control of Nanoparticles in Semiconductor-Polymer Composites. 1. Control via Multiplet Aggregation Numbers in Styrene-Based Random Ionomers [J]. Chem Mater, 1995, 7(6): 1178-1185
[36] Kataoka K. Harada A. Nagasaki Y. Block copolymer micelles for drug delivery: Design,characterization and biological significanae [J]. Advanced Drug Delivery Reviews, 2001, 47(1): 113-131
[37] Henselwood F. Liu G. Water-soluble nanospheres of poly(2-cinnamoylethyl methacrylate)-block-polly(acrylic acid) [J]. Macromolecules, 1997, 30(3): 488-493
[38] Chen X L, Jenekhe S A. Supramolecular Self-Assembly of Three-Dimensional Nanostructures and Microstructures: Microcapsules from Electroactive and Photoactive Rod-Coil-Rod Triblock Copolymers [J]. Macromolecules, 2000, 33(13): 4610-4612
[39] Fréchet J M J, Henmi M, Gitsov I, Aoshima S, Leduc M, Grubbs R B. Self-Condensing Vinyl Polymerization: An Approach to Dendritic Materials [J]. Science, 1995, 269: 1080-1083
[40] Satyananda Barik, Suresh Valiyaveettil. Synthesis and Self-Assembly of Copolymers with Pendant Electroactive Units [J]. Macromolecules, 2008, 41: 6376-6386
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