手性聚酰胺酰亚胺的合成与表征
摘要
手性聚酰胺酰亚胺是一类新型的热稳定性聚合物,可广泛应用于微电子设备、航空航天和汽车制造工业等领域。
本文合成两种类型的手性聚酰胺酰亚胺。首先以冰乙酸作为溶剂,均苯四甲酸二酐(PMDA)分别与L-丙氨酸、L-苯丙氨酸、L-亮氨酸、L-异亮氨酸L-缬氨酸反应合成了五种手性酰亚胺类单体,然后以N-甲基吡咯烷酮(NMP)为溶剂,二甲苯(PX)为共沸剂,用五种合成的手性酰亚胺单体与二苯基甲烷二异氰酸酯(MDI)反应,制备出手性聚酰胺酰亚胺Ⅰ。手性聚酰胺酰亚胺Ⅱ的合成同样采用冰乙酸作为溶剂,均苯四甲酸二酐(PMDA)分别与L-丙氨酸、L-苯丙氨酸、L-亮氨酸、L-异亮氨酸L-缬氨酸反应合成了五种手性酰亚胺类单体,然后制成酰氯,与对氨基苯甲酸反应进行扩链,最后与二苯基二异氰酸酯反应,得到手性聚酰胺酰亚胺Ⅱ。
对制备出的手性酰亚胺单体最佳的反应条件及物料配比进行了探讨,对其反应机理进行了研究。单体通过红外光谱、核磁共振对产物进行了表征。
研究了两类手性聚酰胺酰亚胺的结构与性能。聚合物通过红外光谱、差示量热扫描仪、综合热分析仪对手性聚合物进行了表征。
手性技术是在科学基础上的兴起。虽然取得了一定的成绩,但需进一步的努力。尤其是在合成机理及进一步向生物类物质方向的合成发展,对手性高分子的应用以及手性与结构间的关系等方面的研究还要进一步完善。
Chiral polyamide imides is a new type of thermal stability of the polymer, can be widely used in microelectronics, aerospace and automotive industries and other fields.
Two types of chiral polyamide imide be synthesized in this paper. First to glacial acetic acid as solvent, pyromellitic dianhydride(PMDA), respectively and L-alanine, L-phenylalanine, L-leucine, L-Isoleucine L-Valine Synthesis five chiral imide monomer -s, and then to N-methyl pyrrolidone(NMP) as solvent, xylene(PX) for the azeotropic agent, using five synthetic chiral imide monomer and diphenyl based methane diisocyan -ate(MDI) prepared by the reaction shots of polyamide imideⅠ. Chiral synthesis of polyamide-imideⅡalso used acetic acid as solvent, pyromellitic dianhydri -de(PMDA), respectively and L-alanine, L-phenylalanine, L-leucine, L-differences leucine L-valine was synthesized five chiral imide monomers, and then made into chloride, and the reaction of the amino acid chain extender, and finally with diphenyl diisocyanate reacted chiral poly amide imideⅡ.
On the preparation of chiral imide monomer out the best reaction conditions and ratio of raw materials is discussed and its reaction mechanism was studied. By infrared spectroscopy, nuclear magnetic resonance of the products were characterized.
Two classes of chiral polyamide imide structure and properties will be studyed. By infrared spectroscopy, nuclear magnetic resonance, differential scanning calorimetry instrument, comprehensive thermal analysis of polymers were characterized by opponen -ts.
Chiral Technology is based on the rise in science. Despite some achievements, but further efforts. Particularly in the synthesis mechanism and further direction to the synthesis of substances of biological development, the application of chiral polymers and chiral and structural aspects of the relationship between the research is to further improve.
本文合成两种类型的手性聚酰胺酰亚胺。首先以冰乙酸作为溶剂,均苯四甲酸二酐(PMDA)分别与L-丙氨酸、L-苯丙氨酸、L-亮氨酸、L-异亮氨酸L-缬氨酸反应合成了五种手性酰亚胺类单体,然后以N-甲基吡咯烷酮(NMP)为溶剂,二甲苯(PX)为共沸剂,用五种合成的手性酰亚胺单体与二苯基甲烷二异氰酸酯(MDI)反应,制备出手性聚酰胺酰亚胺Ⅰ。手性聚酰胺酰亚胺Ⅱ的合成同样采用冰乙酸作为溶剂,均苯四甲酸二酐(PMDA)分别与L-丙氨酸、L-苯丙氨酸、L-亮氨酸、L-异亮氨酸L-缬氨酸反应合成了五种手性酰亚胺类单体,然后制成酰氯,与对氨基苯甲酸反应进行扩链,最后与二苯基二异氰酸酯反应,得到手性聚酰胺酰亚胺Ⅱ。
对制备出的手性酰亚胺单体最佳的反应条件及物料配比进行了探讨,对其反应机理进行了研究。单体通过红外光谱、核磁共振对产物进行了表征。
研究了两类手性聚酰胺酰亚胺的结构与性能。聚合物通过红外光谱、差示量热扫描仪、综合热分析仪对手性聚合物进行了表征。
手性技术是在科学基础上的兴起。虽然取得了一定的成绩,但需进一步的努力。尤其是在合成机理及进一步向生物类物质方向的合成发展,对手性高分子的应用以及手性与结构间的关系等方面的研究还要进一步完善。
Chiral polyamide imides is a new type of thermal stability of the polymer, can be widely used in microelectronics, aerospace and automotive industries and other fields.
Two types of chiral polyamide imide be synthesized in this paper. First to glacial acetic acid as solvent, pyromellitic dianhydride(PMDA), respectively and L-alanine, L-phenylalanine, L-leucine, L-Isoleucine L-Valine Synthesis five chiral imide monomer -s, and then to N-methyl pyrrolidone(NMP) as solvent, xylene(PX) for the azeotropic agent, using five synthetic chiral imide monomer and diphenyl based methane diisocyan -ate(MDI) prepared by the reaction shots of polyamide imideⅠ. Chiral synthesis of polyamide-imideⅡalso used acetic acid as solvent, pyromellitic dianhydri -de(PMDA), respectively and L-alanine, L-phenylalanine, L-leucine, L-differences leucine L-valine was synthesized five chiral imide monomers, and then made into chloride, and the reaction of the amino acid chain extender, and finally with diphenyl diisocyanate reacted chiral poly amide imideⅡ.
On the preparation of chiral imide monomer out the best reaction conditions and ratio of raw materials is discussed and its reaction mechanism was studied. By infrared spectroscopy, nuclear magnetic resonance of the products were characterized.
Two classes of chiral polyamide imide structure and properties will be studyed. By infrared spectroscopy, nuclear magnetic resonance, differential scanning calorimetry instrument, comprehensive thermal analysis of polymers were characterized by opponen -ts.
Chiral Technology is based on the rise in science. Despite some achievements, but further efforts. Particularly in the synthesis mechanism and further direction to the synthesis of substances of biological development, the application of chiral polymers and chiral and structural aspects of the relationship between the research is to further improve.
引文
[1] R Buch P, R Reddy AV. Synthesis, characterization and thermal properties of soluble aromatic poly(amide imide)s. [J].Polymer, 2005, 46: 5524-5532
[2] Yang CP, Chen RS, Hung KS.Synthesis and properties of soluble colorless poly(amide-imide)s based on N,N’-bis(3-carboxyphenyl)-4,4-oxydiphthalimide and various aromatic diamines. [J].Polymer 2001; 42: 4569-4577.
[3] Mallakpour SE, Hajipour AR, Khoee S. Polymerization of 4,4'-(Hexafluoroisopropy lidene) N,N'-bis(phthaloyl-L-leucine) diacid chloride with Aromatic Diamines by Microwave-assisted. [J].J Polym Sci Polym Chem(Ed), 2000, 38: 1154-1160.
[4] Kricheldorf H R, Linzer V. Liquid crystalline polyimides: 18.Thermotropic polyi mides based on biphenyl-3,3′,4,4′-tetracarboxylic anhydride[J].Polymer,1995, 36:1893-1902.
[5] Acevedo M, Harris F W. Polyimides derived from 2-methyl-2-propyl-1, 3-bis (4-aminophenoxy)propane and 2,2-dimethyl-1,3-bis (4-aminophenoxy)propane[J]. Polymer, 1994, 35: 4456-4461.
[6] Yang C P, Hsiao S H, Wu K L. Organosoluble and light-colored fluorinated polyimides derived from 2,3-bis(4-amino-2-trifluoromethylphenoxy)naphthalene and aromatic dianhydrides[J]. Polymer,2003, 44:7067-7078.
[7] Huang W, Yan D, Lu Q, Tao P. Preparation of aromatic polyimides highly soluble in conventional solvents[J]. J Polym Sci, Part A: Polym Chem, 2002, 40: 229
[13]帝人.特公昭. J P , 46215513 , 1977.
[14] Buch P R , Reddy A V R. Polymer , 2005 , 46 : 5524～5532.
[15] Koning C , Teuwen L , Lacave2G offin B , et al . Synthesis and properties of alpha,omega-diaminoalkane based poly(amide-imide)s. Polymer ,2001 , 42 : 7247～7256.
[16] Mehdipour2Ataei S , Hatami M. Synthesis and characterization of novel heat resistant poly(amide imide)s. European Polymer Journal , 2005 , 41 : 2010～2015.
[17] Hsiao S H, Lin K H. Polyimides derived from novel asymmetric ether diamine[J]. J Polym Sci, Part A: Polym Chem, 2005,43: 331-341.
[18] Wu S Q, Li W M, Gao C L, et al. Copolymerization of dichlorodiphenylsulfone with bis(chlorophthalimide) catalyzed by NiBr2/PPh3/Zn [J]. Polymer, 2004, 45: 2533-2538.
[19]杜玉杰,张慧敏,许东卫.聚酰胺酰亚胺耐高温绝缘漆的研究[J].河南化工,2004,(10):18-19.
[20] Barikani M, Ataei S M . Preparation and properties of polyimides and polyamideimides from diisocyanates[J] .Journal of Polymer Science : Part A : Polymer Chemistry,1999, (37) :2245-2250.
[21]吴航,郭虹,刘德辉.聚酰胺-酰亚胺耐高温材料的制备和研究[J].沈阳化工学院学报,1999,13(4):258-263.
[22] Chen L W , Ho K S. Synthesis of polyamide-imide by blocked-methylene diisocyanates[J]. Journal of Polymer Science ,Part A : Polymer Chemistry ,1997, (35) :1711-1717.
[23]刘德辉,吴航,厦建峰.端基封闭法合成聚酰胺酰亚胺[J] .绝缘材料, 2002 , (1) :9-11.
[24]刘德辉,刘学贵,吴航,等.整合法合成聚酰胺酰亚胺及应用研究[J].沈阳化工学院学报,2000,14(4) :244-247.
[25]李春成,宋湛谦.脂松香合成聚酰胺酰亚胺研究进展[J ] .塑料工业,1996, (5):94-96.
[26] Alietto M, Chiellini E,Antone SD, Ruggeri G, Solaro R. Chiral polymer catalysts in preparative organic chemistry: a critical overview[J]. Pure Appl Chem, 1988, 60: 415.
[27] Yuki H, Okamoto Y, Okamoto I. Resolution of racemic compounds by optically active poly(triphenylmethyl methacrylate)[J]. Am Chem Soc, 1980, 102: 6358.
[28] Fontanille M, Guyot M. Dordrecht. Recent advances in mechanistic and synthetic aspects of polymerization[M]. Dordrecht ;Boston :D. Reidel ;Norwell, MA,U.S.A. :Sold and distributed in the U.S.A. and Canada by Kluwer Academic Publishers,1987.
[29] Mallakpour SE, Hajipour AR, Vahabi RJ. Synthesis and Characterization of Novel Poly(Amide-Imide)s Based on Bis(p-amidobenzoic acid)-N-Trimellitylimido- L- leucine [J].J Appl Polym Sci, 2002, 84: 35.
[30] Hajipour AR, Zahmatkesh S, Zarei A, Khazdooz L, Ruoho AE. Synthesis and characterization of novel optically active poly(amide-imide)s via direct amidation[J]. European Polymer Journal, 2005, 41: 229.
[31] Mallakpour S, Rafiemanzelat F. Diisocyanate route as a convenient method for the preparation of novel optically active poly(amide–imide)s based on N- trimellitylimido–S–valine [J].European Polymer Journa, 2005, 41: 2945-2955.
[32] Abdol R, Hajipour,Saeed Zahmatkesh, Arnold E. Ruoho.Synthesis and characterization of new optically active and photolable poly (amide-imide)s from N,N′-(3,3′,4,4′-benzophenonetetracarboxylic)-3,3′,4,4′-diimido-di-L-methionine and different diamines [J]. Polymer Bulletin, 2006, 57: 1-10.
[33] S. Mallakpour, F. Rafiemanzelat. Diisocyanate route as a convenient method for the preparation of novel optically active poly(amide–imide)s based on N-trimellitylimido-S-valine[J]. European Polymer Journal, 2005, 41, 2945–2955.
[34] Nieto JL, de La Campa JG, de Adajo. Aliphatic-aromatic polyamide-imides from diisocyanates, 1. 1H and 13C NMR study of polymer structure[J]. Makromol Chem, 1982, 183: 557.
[35] De La Campa JG, de Abajo J, Nieto JL. Aliphatic-aromatic polyamide- imides from diisocyanates[J]. Makromol Chem, 1982, 183: 571.
[36] Chin-Ping Yang, Yu-Yang Su, Mei-Yuan Hsu. Syntheses and properties of fluorinated polyamides and poly(amide imide)s based on 9,9-bis[4-(4-amino-2-trif luromethylphenoxy) phenyl]fluroene, aromatic dicarboxylic acids, and various monotrimellitimides and bistrimellitimides[J]. Colloid Polym Sci , 2006, 284: 990-1000
[37] Khalil Faghihi. New Optically Active Poly(amide-imide)s Based on N,N'-(Pyrome llitoyl)-bis-L-amino Acid and 1,3-Bis(4-aminophenoxy) Propane: Synthesis and Characterization[J]. Journal of Applied Polymer Science, 2007, 109, 74-81.
[38] Shadpour Mallakpour, Elaheh Kowsari. Synthesis and Properties of Novel Soluble and Thermally Stable Optically Active Poly(amide-imide)s from N,N'- (4,4'- Oxydiphthaloyl)-bis-L- phenylalanine Diacid Chloride and Aromatic Diamines.[J]. Polymer Bulletin, 2005, 54, 147-155
[39] Shadpour Mallakpour, Elaheh Kowsari. Thermally Stable and Optically Active Poly(amide-imide)s Derived from 4,4'-(hexafluoroisopropylidene) -N,N'-bis- (phthaloyl -L-methionine) Diacid Chloride and Various Aromatic Diamines: Synthesis and Characterization [J].Polymer Bulletin, 2006, 57: 169-178.
[40] Bradshaw J. S., Aggarwal S. K., Rouse C. A, et al. Polysiloxanes containing thermally stable chiral amide side-chains for capillary gas and supercritical fluid chromatography[J] Chromatogr., 1987, 405: 169-177.
[41] Schuring V. Enantiomer separation by electroch romatography in open tubular co lumns coated with chirasil dex[J]. Liq Chromatogr, 1995, (16): 9551
[42] Liu J F, Huang J X. Chiral Stationary Phases in High-performance Liqiud Chromatography[J]. Acta Chimica Sinica, 1990, (59): 170-175
[43] Xu X R, Shi M Y. Chiral Stationary Phases in Liqiud Chromato- graphy[J]. Chinese Journal of Chromatography, 1988, 7(3): 154-160
[44] Yoshida M, Hatate Y, et al. Metal-imprinted microsphere prepared by surface template polymerization and its application to chromatogra- phy[J]. Polym.Sci.Poly. Chem., 2002, 38:689-691
[45] Takekira H,Hosoya K, et al. Uniform-Sized Molecularly Imprinted Polymer for (S)-Naproxen Selectively Modified with Hydro- philic External Layer[J]. J.Chromatogr.A, 1999, 849(1):334-339.
[46] Uchiyama K, et al. Enantioseparation of D,L-phenylalanine by Mlecular Iprinted polymer Prticlefilled Cpillary Eectrochromatography[J]. Liq Chromatogr Revl Techno1, 1992, 20(12): 1482-1506
[47] Tsutomu Oishi, Synthesis and polymerization of N-substituted maleimides based on L-alanine ester[J]. Haruo Nagata and Hiromori Tsutsumi Polymer, 1998, 39(17):4121-4130
[48] Nicholson G J.,Bayer E. Rapid gas chromatographic separation of amino acid enantiomers with a novel chiral stationary phase [J]. Chromatogr. Sci., 1977,(52): 172-176
[49] Ohtani S, et al. Novel chiral selectors anchored on polydimethylsiloxane as stationary phases for separation of derivatized amino acid enantiomers by capillary gas chromatography[J]. Separation Science, 2007, 29(2): 318-324
[50] Andrea B, Giuseppe G, Renata R. Passerini reaction-Amine Deprotection– Acyl Migration (PADAM):A convenient strategy for the solid-phase preparation of peptidomimetic Compounds[J]. Molecular Diversity, 2001(6): 220-231
[2] Yang CP, Chen RS, Hung KS.Synthesis and properties of soluble colorless poly(amide-imide)s based on N,N’-bis(3-carboxyphenyl)-4,4-oxydiphthalimide and various aromatic diamines. [J].Polymer 2001; 42: 4569-4577.
[3] Mallakpour SE, Hajipour AR, Khoee S. Polymerization of 4,4'-(Hexafluoroisopropy lidene) N,N'-bis(phthaloyl-L-leucine) diacid chloride with Aromatic Diamines by Microwave-assisted. [J].J Polym Sci Polym Chem(Ed), 2000, 38: 1154-1160.
[4] Kricheldorf H R, Linzer V. Liquid crystalline polyimides: 18.Thermotropic polyi mides based on biphenyl-3,3′,4,4′-tetracarboxylic anhydride[J].Polymer,1995, 36:1893-1902.
[5] Acevedo M, Harris F W. Polyimides derived from 2-methyl-2-propyl-1, 3-bis (4-aminophenoxy)propane and 2,2-dimethyl-1,3-bis (4-aminophenoxy)propane[J]. Polymer, 1994, 35: 4456-4461.
[6] Yang C P, Hsiao S H, Wu K L. Organosoluble and light-colored fluorinated polyimides derived from 2,3-bis(4-amino-2-trifluoromethylphenoxy)naphthalene and aromatic dianhydrides[J]. Polymer,2003, 44:7067-7078.
[7] Huang W, Yan D, Lu Q, Tao P. Preparation of aromatic polyimides highly soluble in conventional solvents[J]. J Polym Sci, Part A: Polym Chem, 2002, 40: 229
[13]帝人.特公昭. J P , 46215513 , 1977.
[14] Buch P R , Reddy A V R. Polymer , 2005 , 46 : 5524～5532.
[15] Koning C , Teuwen L , Lacave2G offin B , et al . Synthesis and properties of alpha,omega-diaminoalkane based poly(amide-imide)s. Polymer ,2001 , 42 : 7247～7256.
[16] Mehdipour2Ataei S , Hatami M. Synthesis and characterization of novel heat resistant poly(amide imide)s. European Polymer Journal , 2005 , 41 : 2010～2015.
[17] Hsiao S H, Lin K H. Polyimides derived from novel asymmetric ether diamine[J]. J Polym Sci, Part A: Polym Chem, 2005,43: 331-341.
[18] Wu S Q, Li W M, Gao C L, et al. Copolymerization of dichlorodiphenylsulfone with bis(chlorophthalimide) catalyzed by NiBr2/PPh3/Zn [J]. Polymer, 2004, 45: 2533-2538.
[19]杜玉杰,张慧敏,许东卫.聚酰胺酰亚胺耐高温绝缘漆的研究[J].河南化工,2004,(10):18-19.
[20] Barikani M, Ataei S M . Preparation and properties of polyimides and polyamideimides from diisocyanates[J] .Journal of Polymer Science : Part A : Polymer Chemistry,1999, (37) :2245-2250.
[21]吴航,郭虹,刘德辉.聚酰胺-酰亚胺耐高温材料的制备和研究[J].沈阳化工学院学报,1999,13(4):258-263.
[22] Chen L W , Ho K S. Synthesis of polyamide-imide by blocked-methylene diisocyanates[J]. Journal of Polymer Science ,Part A : Polymer Chemistry ,1997, (35) :1711-1717.
[23]刘德辉,吴航,厦建峰.端基封闭法合成聚酰胺酰亚胺[J] .绝缘材料, 2002 , (1) :9-11.
[24]刘德辉,刘学贵,吴航,等.整合法合成聚酰胺酰亚胺及应用研究[J].沈阳化工学院学报,2000,14(4) :244-247.
[25]李春成,宋湛谦.脂松香合成聚酰胺酰亚胺研究进展[J ] .塑料工业,1996, (5):94-96.
[26] Alietto M, Chiellini E,Antone SD, Ruggeri G, Solaro R. Chiral polymer catalysts in preparative organic chemistry: a critical overview[J]. Pure Appl Chem, 1988, 60: 415.
[27] Yuki H, Okamoto Y, Okamoto I. Resolution of racemic compounds by optically active poly(triphenylmethyl methacrylate)[J]. Am Chem Soc, 1980, 102: 6358.
[28] Fontanille M, Guyot M. Dordrecht. Recent advances in mechanistic and synthetic aspects of polymerization[M]. Dordrecht ;Boston :D. Reidel ;Norwell, MA,U.S.A. :Sold and distributed in the U.S.A. and Canada by Kluwer Academic Publishers,1987.
[29] Mallakpour SE, Hajipour AR, Vahabi RJ. Synthesis and Characterization of Novel Poly(Amide-Imide)s Based on Bis(p-amidobenzoic acid)-N-Trimellitylimido- L- leucine [J].J Appl Polym Sci, 2002, 84: 35.
[30] Hajipour AR, Zahmatkesh S, Zarei A, Khazdooz L, Ruoho AE. Synthesis and characterization of novel optically active poly(amide-imide)s via direct amidation[J]. European Polymer Journal, 2005, 41: 229.
[31] Mallakpour S, Rafiemanzelat F. Diisocyanate route as a convenient method for the preparation of novel optically active poly(amide–imide)s based on N- trimellitylimido–S–valine [J].European Polymer Journa, 2005, 41: 2945-2955.
[32] Abdol R, Hajipour,Saeed Zahmatkesh, Arnold E. Ruoho.Synthesis and characterization of new optically active and photolable poly (amide-imide)s from N,N′-(3,3′,4,4′-benzophenonetetracarboxylic)-3,3′,4,4′-diimido-di-L-methionine and different diamines [J]. Polymer Bulletin, 2006, 57: 1-10.
[33] S. Mallakpour, F. Rafiemanzelat. Diisocyanate route as a convenient method for the preparation of novel optically active poly(amide–imide)s based on N-trimellitylimido-S-valine[J]. European Polymer Journal, 2005, 41, 2945–2955.
[34] Nieto JL, de La Campa JG, de Adajo. Aliphatic-aromatic polyamide-imides from diisocyanates, 1. 1H and 13C NMR study of polymer structure[J]. Makromol Chem, 1982, 183: 557.
[35] De La Campa JG, de Abajo J, Nieto JL. Aliphatic-aromatic polyamide- imides from diisocyanates[J]. Makromol Chem, 1982, 183: 571.
[36] Chin-Ping Yang, Yu-Yang Su, Mei-Yuan Hsu. Syntheses and properties of fluorinated polyamides and poly(amide imide)s based on 9,9-bis[4-(4-amino-2-trif luromethylphenoxy) phenyl]fluroene, aromatic dicarboxylic acids, and various monotrimellitimides and bistrimellitimides[J]. Colloid Polym Sci , 2006, 284: 990-1000
[37] Khalil Faghihi. New Optically Active Poly(amide-imide)s Based on N,N'-(Pyrome llitoyl)-bis-L-amino Acid and 1,3-Bis(4-aminophenoxy) Propane: Synthesis and Characterization[J]. Journal of Applied Polymer Science, 2007, 109, 74-81.
[38] Shadpour Mallakpour, Elaheh Kowsari. Synthesis and Properties of Novel Soluble and Thermally Stable Optically Active Poly(amide-imide)s from N,N'- (4,4'- Oxydiphthaloyl)-bis-L- phenylalanine Diacid Chloride and Aromatic Diamines.[J]. Polymer Bulletin, 2005, 54, 147-155
[39] Shadpour Mallakpour, Elaheh Kowsari. Thermally Stable and Optically Active Poly(amide-imide)s Derived from 4,4'-(hexafluoroisopropylidene) -N,N'-bis- (phthaloyl -L-methionine) Diacid Chloride and Various Aromatic Diamines: Synthesis and Characterization [J].Polymer Bulletin, 2006, 57: 169-178.
[40] Bradshaw J. S., Aggarwal S. K., Rouse C. A, et al. Polysiloxanes containing thermally stable chiral amide side-chains for capillary gas and supercritical fluid chromatography[J] Chromatogr., 1987, 405: 169-177.
[41] Schuring V. Enantiomer separation by electroch romatography in open tubular co lumns coated with chirasil dex[J]. Liq Chromatogr, 1995, (16): 9551
[42] Liu J F, Huang J X. Chiral Stationary Phases in High-performance Liqiud Chromatography[J]. Acta Chimica Sinica, 1990, (59): 170-175
[43] Xu X R, Shi M Y. Chiral Stationary Phases in Liqiud Chromato- graphy[J]. Chinese Journal of Chromatography, 1988, 7(3): 154-160
[44] Yoshida M, Hatate Y, et al. Metal-imprinted microsphere prepared by surface template polymerization and its application to chromatogra- phy[J]. Polym.Sci.Poly. Chem., 2002, 38:689-691
[45] Takekira H,Hosoya K, et al. Uniform-Sized Molecularly Imprinted Polymer for (S)-Naproxen Selectively Modified with Hydro- philic External Layer[J]. J.Chromatogr.A, 1999, 849(1):334-339.
[46] Uchiyama K, et al. Enantioseparation of D,L-phenylalanine by Mlecular Iprinted polymer Prticlefilled Cpillary Eectrochromatography[J]. Liq Chromatogr Revl Techno1, 1992, 20(12): 1482-1506
[47] Tsutomu Oishi, Synthesis and polymerization of N-substituted maleimides based on L-alanine ester[J]. Haruo Nagata and Hiromori Tsutsumi Polymer, 1998, 39(17):4121-4130
[48] Nicholson G J.,Bayer E. Rapid gas chromatographic separation of amino acid enantiomers with a novel chiral stationary phase [J]. Chromatogr. Sci., 1977,(52): 172-176
[49] Ohtani S, et al. Novel chiral selectors anchored on polydimethylsiloxane as stationary phases for separation of derivatized amino acid enantiomers by capillary gas chromatography[J]. Separation Science, 2007, 29(2): 318-324
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