增亮膜用双端丙烯酸酯类液晶化合物的合成与表征
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摘要
增亮膜用液晶材料是近年涌现出来的研究热点,双端丙烯酸酯类液晶化合物是其中重要的一种原料,它有较好的光电性能,这类液晶化合物在信息存储和混晶材料的配制等方面也具有很大的应用潜力。本文对两个增亮膜用双端丙烯酸酯类液晶材料的合成进行了研究,根据链段的不同,采用了不同的工艺路线,合成出了两种双端丙烯酸酯类液晶化合物,一种含碳三烷氧基链段,一种含碳四烷氧基链段。
第一种方案,合成含碳三烷氧基链段的双端丙烯酸酯类液晶化合物。合成分为以下三步:第一步是对羟基苯甲酸与3-氯丙醇反应生成4-(3-羟基丙氧基)苯甲酸,从而在对羟基苯甲酸上引入了柔性链段;第二步是将产物与丙烯酰氯反应,从而生成含双键的4-(3-丙烯酸酯丙氧基)苯甲酸;第三步是将上一步产物与邻甲基对苯二酚在DCC和DMAP催化下进行酯化反应,从而生成含碳三液晶基元的双端丙烯酸酯类液晶化合物。
第二种方案,合成含碳四烷氧基链段的双端丙烯酸酯类液晶化合物。合成分为以下四步:第一步是四氢呋喃在氯化锌催化下与乙酰氯反应生成4-氯丁基乙酸酯,得到保护的4-氯丁醇;第二步是作为液晶基元的4-(4-羟基丁氧基)苯甲酸的合成,首先,4-乙酸酯丁基氯与对羟基苯甲酸乙酯在DMF中进行醚化,然后将产物在碱性条件下水解,最后用盐酸酸化得所要的4-(4-羟基丁氧基)苯甲酸;第三步是将产物与丙烯酰氯反应,从而生成含双键的4-(4-丙烯酸酯丁氧基)苯甲酸;第四步是将上一步产物与邻甲基对苯二酚在DCC和DMAP催化下进行酯化反应,从而生成含碳四液晶基元的双端丙烯酸酯类液晶化合物。
采用显微熔点测定仪、红外光谱、核磁、DSC等手段对制备的两种双端丙烯酸酯类液晶分子进行了表征和性能测试。结果表明,两种液晶分子都具有非常好的液晶性,两者都为向列相液晶分子,而且它们的液晶性能很稳定。
Liquid crystals used in brightness enhancement film, is a new style function materials in these years. Double-side acrylate liquid crystallines with good photo-electricity performance is one important materials of BEF. It has good application potentiality in the field of information storage and mixed liquid crystals. Two double-side chain liquid crystal acrylates, one with three carbon spacers and the other with four carbon spacers, were prepared in different processes.
In the first process, liquid crystal double-side acrylate with three carbon alkoxy chain was synthesized, which is divided into three steps: firstly, 4-(3-Hydroxypropoxy) benzoic acid was made by p-hydroxybenzoic acid with 3-Chloropropanol, and the flexible spaces were added into p-hydroxybenzoic acid; secondly, 4-(3-Acryloyl oxypropyloxy) benzoic acid was produced by the product with acryloyl chloride; thirdly, it was esterificated with o-hydroquinone in the DCC and DMAP-catalyzed, in order to generate the double-side acrylate liquid crystal with three carbon alkoxy chain mesogenic unit.
In the second process, liquid crystal double-side acrylate with four carbon alkoxy chain was synthesized, which is divided into three steps: firstly, 4-Chlorobutyl acetate was made by Tetrahydrofuran and Acetic chloride with ZnCl2 as a catalyst; sencondly, the synthesis of 4-(4-Hydroxybutoxy) benzoic acid as mesogenic unit, was produced by 4-Chlorobutyl acetate with ethyl p-hydroxybenzoate in DMF, then hydrolysis under alkaline condition, and acidification with hydrochloric acid; secondly, 4-(4-Acryloyl oxybutoxy) benzoic acid was produced by the product with acryloyl chloride; thirdly, it was esterificated with o-hydroquinone in the DCC and DMAP-catalyzed, in order to generate the double-side acrylate liquid crystal with three carbon alkoxy chain mesogenic unit.
Result of performance measurement of the two double-side acrylate liquid crystallines by melting point apparatus、IR and DSC shows that they are of perfect liquid crystal performance, the two are all nematic liquid crystals, and their liquid crystal performance is very stable.
第一种方案,合成含碳三烷氧基链段的双端丙烯酸酯类液晶化合物。合成分为以下三步:第一步是对羟基苯甲酸与3-氯丙醇反应生成4-(3-羟基丙氧基)苯甲酸,从而在对羟基苯甲酸上引入了柔性链段;第二步是将产物与丙烯酰氯反应,从而生成含双键的4-(3-丙烯酸酯丙氧基)苯甲酸;第三步是将上一步产物与邻甲基对苯二酚在DCC和DMAP催化下进行酯化反应,从而生成含碳三液晶基元的双端丙烯酸酯类液晶化合物。
第二种方案,合成含碳四烷氧基链段的双端丙烯酸酯类液晶化合物。合成分为以下四步:第一步是四氢呋喃在氯化锌催化下与乙酰氯反应生成4-氯丁基乙酸酯,得到保护的4-氯丁醇;第二步是作为液晶基元的4-(4-羟基丁氧基)苯甲酸的合成,首先,4-乙酸酯丁基氯与对羟基苯甲酸乙酯在DMF中进行醚化,然后将产物在碱性条件下水解,最后用盐酸酸化得所要的4-(4-羟基丁氧基)苯甲酸;第三步是将产物与丙烯酰氯反应,从而生成含双键的4-(4-丙烯酸酯丁氧基)苯甲酸;第四步是将上一步产物与邻甲基对苯二酚在DCC和DMAP催化下进行酯化反应,从而生成含碳四液晶基元的双端丙烯酸酯类液晶化合物。
采用显微熔点测定仪、红外光谱、核磁、DSC等手段对制备的两种双端丙烯酸酯类液晶分子进行了表征和性能测试。结果表明,两种液晶分子都具有非常好的液晶性,两者都为向列相液晶分子,而且它们的液晶性能很稳定。
Liquid crystals used in brightness enhancement film, is a new style function materials in these years. Double-side acrylate liquid crystallines with good photo-electricity performance is one important materials of BEF. It has good application potentiality in the field of information storage and mixed liquid crystals. Two double-side chain liquid crystal acrylates, one with three carbon spacers and the other with four carbon spacers, were prepared in different processes.
In the first process, liquid crystal double-side acrylate with three carbon alkoxy chain was synthesized, which is divided into three steps: firstly, 4-(3-Hydroxypropoxy) benzoic acid was made by p-hydroxybenzoic acid with 3-Chloropropanol, and the flexible spaces were added into p-hydroxybenzoic acid; secondly, 4-(3-Acryloyl oxypropyloxy) benzoic acid was produced by the product with acryloyl chloride; thirdly, it was esterificated with o-hydroquinone in the DCC and DMAP-catalyzed, in order to generate the double-side acrylate liquid crystal with three carbon alkoxy chain mesogenic unit.
In the second process, liquid crystal double-side acrylate with four carbon alkoxy chain was synthesized, which is divided into three steps: firstly, 4-Chlorobutyl acetate was made by Tetrahydrofuran and Acetic chloride with ZnCl2 as a catalyst; sencondly, the synthesis of 4-(4-Hydroxybutoxy) benzoic acid as mesogenic unit, was produced by 4-Chlorobutyl acetate with ethyl p-hydroxybenzoate in DMF, then hydrolysis under alkaline condition, and acidification with hydrochloric acid; secondly, 4-(4-Acryloyl oxybutoxy) benzoic acid was produced by the product with acryloyl chloride; thirdly, it was esterificated with o-hydroquinone in the DCC and DMAP-catalyzed, in order to generate the double-side acrylate liquid crystal with three carbon alkoxy chain mesogenic unit.
Result of performance measurement of the two double-side acrylate liquid crystallines by melting point apparatus、IR and DSC shows that they are of perfect liquid crystal performance, the two are all nematic liquid crystals, and their liquid crystal performance is very stable.
引文
[1]高鸿锦,董友梅.液晶与平板显示技术[M].北京:北京邮电大学出版社, 2007: 102-105
[2] Oseen CW. The Theory of Liquid Crystals [J]. Transactions of the Faraday Society, 1933, 29: 883-899
[3]周其凤,王新久.液晶高分子[M].北京:科学出版社, 1994: 65-109
[4]谢毓章.液晶物理学.第二版.北京:科学出版社, 1998: 56-59
[5] Friedrich Reinitzer. Beitr?ge zur Kenntniss des Cholesterin [J]. Monatshefte für Chemie, 1888, 9: 421-441
[6] Lehmann OZ. Antisoiling dust-repellent laminated sheet [J]. Physik.Chem., 1889, 4: 462-473
[7] Demus D, Richter L. The Texture of Liquid Crystals [J]. Applied Physics Letters, 1972, 13: 91-100
[8] Baur G, Stieb A, Meirer G. Application of Infrared ATR Spectroscopy to Liquid Crystals [J]. Molecular Crystals and Liquid Crystals, 1973, 22: 261-267
[9] Blinov LM, Electrooptics and Magnetoopitcs of Liquid Crystal [J]. Molecular Crystal and Liquid Crystal, 1978, 43: 212-217
[10] Bose E. Behaviour of Liquid Crystal [J]. Journal of Physics, 1972, 8: 513-518
[11] Tsvekov V. The Order-disorder Phase Transition in Liquid Crystals as a Function of Molecular Structure [J]. Molecular Crystals and Liquid Crystals, 1966, 1: 293-298
[12] Oseen CW. The Theory of Liquid Crystals [J]. Transactions of the Faraday Society,1933,29:883-899
[13] Takizawa K, Fjjii T, Kawakita M, et al. Spatial light modulators for projection displays [J]. Applied Optics, 1997, V36: 5732-5747
[14] Glenn H Brown, Wilfred G Shaw. The Mesomorphic State - Liquid Crystals [J]. Chemical Reviews, 1957, 57 (6): 1049–1157
[15] Kazuo Ohno, Akira Isogai, Fumihiko Onabe. Retention behavior of size and aluminum components in handsheets prepared in rosin soap size-alum systems [J]. The Japan Wood Research Society, 1999, 45: 238-244
[16] Tomasik, Michelle R, Collings, Peter J. Aggregation behavior and chromonic liquid crystal phase of a dye derived from naphthalenecarboxylic acid. Journal of Physical Chemistry B (2008), 112(32), 9883-89
[17] Miller, Wilmer G.; Rai, Juey H.; Wee, Elizabeth L. Liquid crystal-isotropic phase equilibria in stiff chain polymers. Liquid Crystals and Ordered Fluids, 1973, 2: 243-55
[18] Hosemann, R.; Loboda-Cackovic J, Cackovic H. New Type of liquid crystal [J]. Berichte der Bunsen-Gesellschaft, 1973, 77(12): 1044-7
[19] Luckhurst, GR, Ptak M, Sanson A. Molecular organization within the smectic C mesophase of the liquid crystal 4, 4'-diheptyloxyazoxybenzene [J]. Journal of the Chemical Society, Faraday Transactions 2: Molecular and Chemical Physics, 1973, 69(12): 1752-66
[20] Onnagawa, Hiroyoshi, Miyashita. Molecular orientation and wall effect of nematic liquid crystal cells [J]. Oyo Butsuri, 1973, 42 (2): 133-41
[21] Stinson, TW, Litster JD. Correlation range of fluctuations of short-range order in the isotropic phase of a liquid crystal. Physical Review Letters, 1973, 30(15):47-51
[22] Silverman, David N, Dailey, Benjamin P. Chemical-shift anisotropy in liquid crystal solvents [J]. Journal of Chemical Physics, 1969, 51(2): 655-63
[23] Barrall, Edward M, Julian Frank. Specific heats of nematic, smectic, and cholesteric liquid crystals by differential scanning calorimetry. Journal of Physical Chemistry, 1967, 71(4): 895-900
[24] Vainshtein, BK, Chistyakov, IG. Molecular structure and growth of liquid crystals [J]. Rost Kristallov, 1965, 5: 163-72
[25] Carr, Edward F. Influence of electric and magnetic fields on the dielectric constant and loss of the liquid crystal anisaldazine [J]. Journal of Chemical Physics, 1963, 38: 1536-40
[26]曹家恒,等著.新一代多媒体技术与应用.武汉:武汉大学出版社, 2006: 97-102
[27] Choi Jin-Sung, Jung Jin-Mi. Diffusing plate with improved brightness, and backlight assembly and display device including the same [P]. US2006142448, 2006
[28] Schott Cecile, Patrick John, Adlem Kevin. Liquid crystal system and liquid crystal display [P]. WO 2006063662, 2006
[29] Finkdmann H, Kiechel U. Behavior of Liquid Crystalline Side Chain Polymers in an Electric Field [J]. Molecular Crystals and Liquid Crystals, 1983, 94: 343-58.
[30] Patrick, Keller. Synthesis of liquid-crystalline side-chain polyacrylates by solid-liquid phase-transfer catalysis without added solvent [J]. Macromolecules,1987, 20: 462-464
[31] Aloir Merlo, Olga M. Chiral Liquid-Crystalline Polyacrylates from (S)-(-)- 2-methyl-1-butanol. Synthesis, Mesomorphic Properties and Light Scattering [J]. Journal of the Brazilian Chemical Society, 2001, 12: 184-191
[32] Fan-Bao Meng, Bao-Yan Zhang, Jing-Yan Liu. Main-chain liquid-crystalline ionomers bearing potassium sulfonate groups [J]. Journal of Applied Polymer Science, 2005, 96: 2021-2026
[33] Charles Sangmam, Jean-Yves Winum, Marc Lucas. A Simple, General and Efficient Method for O and N-Retinoylation. Application to the Synthesis of 2-Retinoyl-Lecithin [J]. Synthetic Communications, 1998, 28 (16) : 2945-2958
[34] Parish HA, Purchll WP. Topical Prodrugs for Treatment of Acne and Skin Diseases [P]. US4677120, 1987
[35] Samokyszyn VM, Gall WE, Zawada G. 4-Hydroxyretinoic Acid, a Novel Substrate for Human Liver Microsomal UDP-glucuronosyltransferase(s) and Recombinant UGT2B7 [J]. Journal of Biological Chemistry, 2000; 275: 6908-6914
[36] Cowling SJ, Hall AW, Goodby. John W. Examination of the interlayer strength of smectic liquid crystals through the study of partially fluorinated and branched fluorinated end-groups [J]. Journal of Materials Chemistry, 2006, 16 (22): 2181-91
[37] Cook James G, Dickson James T, Lowe Arthur R. New highly polymeric linear esters and the production of filaments, fibers, and the like therefrom [P]. GB604985, 1976
[38] Edward C, Taylor GH, Hawks. Thallium in organic synthesis I Alkylation and acylation of beta-dicarbonyl compounds [J]. Journal of the American Chemical Society, 1968, 90(9): 2421-22
[39] Whitcombe MJ, Davis FJ, Gilbert A. The convenient synthesis of a liquid crystalline polyacrylate with a tetramethylene spacer [J]. Polymer Communications, 1991, 32(12): 380-1
[40] Nishikawa Hideyuki, Goto Haruyoshi. Manufacture of benzoic acid group- containing (meth) acrylic acid esters [P]. JP08310996, 1996
[41] Floyd DE, Miller SE. Organic Syntheses, 1963, 4: 141
[42] David MP, Robert L, Cargill. Alkylation of 2-carbethozycyclopentanone in dimethyl sulfoxide [J]. J. Org. Chem., 1967, 32 (12):4064-65
[43] Aloir Merlo, Olga Ritter. Chiral Liquid-Crystalline Polyacrylates from (S)-(-)-2-methyl-1-butanol. Synthesis, Mesomorphic Properties and Light Scattering [J]. Journal of Brazilian Chemical Society, 2001, 12: 184-91
[44] Barmatov EB, Bobrovsky AY, Pebalk DA. Cholesteric mesophase of the hydrogen-bonded blends of liquid crystalline ionogenic copolymers with a low molecular weight chiral dopant [J]. Polymer Chemistry, 1999, 37 (16): 3215-3225
[45] Andruzzi Luisa, D'Apollo Francesca, Galli Giancarlo. Synthesis and Structure Characterization of Liquid Crystalline Polyacrylates with Unconventional Fluoroalkylphenyl Mesogens [J]. Macromolecules, 2001, 34 (22): 7707-7714
[46] Barmatov EB, Filippov AP, Shibaev VP. Side group functionalized liquid crystalline polymers and blends VIII. Nematic and SmAre phase formation in hydrogen-bonded blends of smectic side group LC polymers and a low molar mass dopant [J]. Liquid Crystals, 2001, 28 (4): 511-523
[47] Fitch John W, Payne Wyatt G, Westmoreland Donald. Platinum-catalyzed acylative cleavage of cyclic ethers [J]. Journal of Organic Chemistry, 1983, 48(5): 751-3
[48] Pri-Bar I, Stille J K. Acylative cleavage of ethers catalyzed by triorganotin halides and palladium (II) complexes [J]. Journal of Organic Chemistry, 1982, 47(7): 1215-20
[49] Commercon A, Normant JF, Villieras J. Substitution of 1-halo-alkynes by organometallic copper derivatives. Route to a new class of synthons: application to the synthesis of bombykol [J]. Tetrahedron, 1980, 36(9): 1215-21
[50] Broer, DJ, Vriens L. Laser-induced optical recording in thin films: Modeling of the hole opening and experiments with organic sublayers [J]. Applied Physics A: Solids and Surfaces, 1983, 32 (3): 107-23
[51] Broer DJ, Mol GN. Oriented polymers obtained by UV-polymerization of oriented low molecular weight species [J]. Polymeric Materials Science and Engineering, 1986, 55: 540-4
[52] Broer DJ, Gossink RG, Hikmet R. Oriented polymer networks obtained by photo polymerization of liquid-crystalline monomers [J]. Angewandte Makromolekulare Chemie , 1990, 183: 45-66
[53] Broer DJ, Heynderickx I. Three-dimensionally ordered polymer networks with a helicoidal structure. Macromolecules , 1990, 23(9): 2474-7
[54] Broer DJ, Mol GN, Challa G. Temperature effects on the kinetics of photoinitiated polymerization of dimethacrylates [J]. Polymer, 1991, 32(4): 690-5
[55] Hikmet R, Broer DJ. Dynamic mechanical properties of anisotropic networks formed by liquid-crystalline acrylates [J]. Polymer , 1991, 32(9): 1627-32
[56] Heynderickx I, Broer DJ. The use of cholesterically polymer networks in practical applications [J]. Molecular Crystals and Liquid Crystals, 1991, 203: 113-26
[57] Hikmet R, Zwerver B, Broer D. Anisotropic polymerization shrinkage behavior of liquid-crystalline diacrylates [J]. Polymer, 1992), V33(1): 89-95
[58] Broer DJ, Lub J, Mol GN. Synthesis and photopolymerization of a liquid-crystalline diepoxide [J]. Macromolecules, 1993, 26(6): 1244-7
[59] Heynderickx I, Broer DJ, Tervoort-Engelen Y. Visualization of the cholesteric texture near a Grandjean line [J]. Liquid Crystals, 1993, 15 (5): 745-8
[60] Lub J., Broer DJ, Hikmet R. Synthesis and photopolymerization of cholesteric liquid crystalline diacrylates [J]. Liquid Crystals, 1995, 18 (2): 319-26
[61] Broer DJ, Lub J, Mol GN. Wide-band reflective polarizers from cholesteric polymer networks with a pitch gradient [J]. Nature (London), 1995, 378 (6556): 467-9
[62] Lub J, Broer DJ, Antonio ME, Martinez. The formation of a liquid crystalline main chain polymer by means of photopolymerization [J]. Liquid Crystals, 1998, 24 (3): 375-79
[63] Bhar Sanjay, Ranu Brindaban C. Zinc-Promoted Selective Cleavage of Ethers in Presence of Acyl Chloride. Journal of Organic Chemistry, 1995, 60 (3): 745-7
[64] Chen H, Philip, Katsis, Chen H. Deterministic Synthesis and Optical Properties of Glassy Chiral-Nematic Liquid Crystals [J]. Chemistry of Materials, 2003, 15 (13): 2534-2542
[2] Oseen CW. The Theory of Liquid Crystals [J]. Transactions of the Faraday Society, 1933, 29: 883-899
[3]周其凤,王新久.液晶高分子[M].北京:科学出版社, 1994: 65-109
[4]谢毓章.液晶物理学.第二版.北京:科学出版社, 1998: 56-59
[5] Friedrich Reinitzer. Beitr?ge zur Kenntniss des Cholesterin [J]. Monatshefte für Chemie, 1888, 9: 421-441
[6] Lehmann OZ. Antisoiling dust-repellent laminated sheet [J]. Physik.Chem., 1889, 4: 462-473
[7] Demus D, Richter L. The Texture of Liquid Crystals [J]. Applied Physics Letters, 1972, 13: 91-100
[8] Baur G, Stieb A, Meirer G. Application of Infrared ATR Spectroscopy to Liquid Crystals [J]. Molecular Crystals and Liquid Crystals, 1973, 22: 261-267
[9] Blinov LM, Electrooptics and Magnetoopitcs of Liquid Crystal [J]. Molecular Crystal and Liquid Crystal, 1978, 43: 212-217
[10] Bose E. Behaviour of Liquid Crystal [J]. Journal of Physics, 1972, 8: 513-518
[11] Tsvekov V. The Order-disorder Phase Transition in Liquid Crystals as a Function of Molecular Structure [J]. Molecular Crystals and Liquid Crystals, 1966, 1: 293-298
[12] Oseen CW. The Theory of Liquid Crystals [J]. Transactions of the Faraday Society,1933,29:883-899
[13] Takizawa K, Fjjii T, Kawakita M, et al. Spatial light modulators for projection displays [J]. Applied Optics, 1997, V36: 5732-5747
[14] Glenn H Brown, Wilfred G Shaw. The Mesomorphic State - Liquid Crystals [J]. Chemical Reviews, 1957, 57 (6): 1049–1157
[15] Kazuo Ohno, Akira Isogai, Fumihiko Onabe. Retention behavior of size and aluminum components in handsheets prepared in rosin soap size-alum systems [J]. The Japan Wood Research Society, 1999, 45: 238-244
[16] Tomasik, Michelle R, Collings, Peter J. Aggregation behavior and chromonic liquid crystal phase of a dye derived from naphthalenecarboxylic acid. Journal of Physical Chemistry B (2008), 112(32), 9883-89
[17] Miller, Wilmer G.; Rai, Juey H.; Wee, Elizabeth L. Liquid crystal-isotropic phase equilibria in stiff chain polymers. Liquid Crystals and Ordered Fluids, 1973, 2: 243-55
[18] Hosemann, R.; Loboda-Cackovic J, Cackovic H. New Type of liquid crystal [J]. Berichte der Bunsen-Gesellschaft, 1973, 77(12): 1044-7
[19] Luckhurst, GR, Ptak M, Sanson A. Molecular organization within the smectic C mesophase of the liquid crystal 4, 4'-diheptyloxyazoxybenzene [J]. Journal of the Chemical Society, Faraday Transactions 2: Molecular and Chemical Physics, 1973, 69(12): 1752-66
[20] Onnagawa, Hiroyoshi, Miyashita. Molecular orientation and wall effect of nematic liquid crystal cells [J]. Oyo Butsuri, 1973, 42 (2): 133-41
[21] Stinson, TW, Litster JD. Correlation range of fluctuations of short-range order in the isotropic phase of a liquid crystal. Physical Review Letters, 1973, 30(15):47-51
[22] Silverman, David N, Dailey, Benjamin P. Chemical-shift anisotropy in liquid crystal solvents [J]. Journal of Chemical Physics, 1969, 51(2): 655-63
[23] Barrall, Edward M, Julian Frank. Specific heats of nematic, smectic, and cholesteric liquid crystals by differential scanning calorimetry. Journal of Physical Chemistry, 1967, 71(4): 895-900
[24] Vainshtein, BK, Chistyakov, IG. Molecular structure and growth of liquid crystals [J]. Rost Kristallov, 1965, 5: 163-72
[25] Carr, Edward F. Influence of electric and magnetic fields on the dielectric constant and loss of the liquid crystal anisaldazine [J]. Journal of Chemical Physics, 1963, 38: 1536-40
[26]曹家恒,等著.新一代多媒体技术与应用.武汉:武汉大学出版社, 2006: 97-102
[27] Choi Jin-Sung, Jung Jin-Mi. Diffusing plate with improved brightness, and backlight assembly and display device including the same [P]. US2006142448, 2006
[28] Schott Cecile, Patrick John, Adlem Kevin. Liquid crystal system and liquid crystal display [P]. WO 2006063662, 2006
[29] Finkdmann H, Kiechel U. Behavior of Liquid Crystalline Side Chain Polymers in an Electric Field [J]. Molecular Crystals and Liquid Crystals, 1983, 94: 343-58.
[30] Patrick, Keller. Synthesis of liquid-crystalline side-chain polyacrylates by solid-liquid phase-transfer catalysis without added solvent [J]. Macromolecules,1987, 20: 462-464
[31] Aloir Merlo, Olga M. Chiral Liquid-Crystalline Polyacrylates from (S)-(-)- 2-methyl-1-butanol. Synthesis, Mesomorphic Properties and Light Scattering [J]. Journal of the Brazilian Chemical Society, 2001, 12: 184-191
[32] Fan-Bao Meng, Bao-Yan Zhang, Jing-Yan Liu. Main-chain liquid-crystalline ionomers bearing potassium sulfonate groups [J]. Journal of Applied Polymer Science, 2005, 96: 2021-2026
[33] Charles Sangmam, Jean-Yves Winum, Marc Lucas. A Simple, General and Efficient Method for O and N-Retinoylation. Application to the Synthesis of 2-Retinoyl-Lecithin [J]. Synthetic Communications, 1998, 28 (16) : 2945-2958
[34] Parish HA, Purchll WP. Topical Prodrugs for Treatment of Acne and Skin Diseases [P]. US4677120, 1987
[35] Samokyszyn VM, Gall WE, Zawada G. 4-Hydroxyretinoic Acid, a Novel Substrate for Human Liver Microsomal UDP-glucuronosyltransferase(s) and Recombinant UGT2B7 [J]. Journal of Biological Chemistry, 2000; 275: 6908-6914
[36] Cowling SJ, Hall AW, Goodby. John W. Examination of the interlayer strength of smectic liquid crystals through the study of partially fluorinated and branched fluorinated end-groups [J]. Journal of Materials Chemistry, 2006, 16 (22): 2181-91
[37] Cook James G, Dickson James T, Lowe Arthur R. New highly polymeric linear esters and the production of filaments, fibers, and the like therefrom [P]. GB604985, 1976
[38] Edward C, Taylor GH, Hawks. Thallium in organic synthesis I Alkylation and acylation of beta-dicarbonyl compounds [J]. Journal of the American Chemical Society, 1968, 90(9): 2421-22
[39] Whitcombe MJ, Davis FJ, Gilbert A. The convenient synthesis of a liquid crystalline polyacrylate with a tetramethylene spacer [J]. Polymer Communications, 1991, 32(12): 380-1
[40] Nishikawa Hideyuki, Goto Haruyoshi. Manufacture of benzoic acid group- containing (meth) acrylic acid esters [P]. JP08310996, 1996
[41] Floyd DE, Miller SE. Organic Syntheses, 1963, 4: 141
[42] David MP, Robert L, Cargill. Alkylation of 2-carbethozycyclopentanone in dimethyl sulfoxide [J]. J. Org. Chem., 1967, 32 (12):4064-65
[43] Aloir Merlo, Olga Ritter. Chiral Liquid-Crystalline Polyacrylates from (S)-(-)-2-methyl-1-butanol. Synthesis, Mesomorphic Properties and Light Scattering [J]. Journal of Brazilian Chemical Society, 2001, 12: 184-91
[44] Barmatov EB, Bobrovsky AY, Pebalk DA. Cholesteric mesophase of the hydrogen-bonded blends of liquid crystalline ionogenic copolymers with a low molecular weight chiral dopant [J]. Polymer Chemistry, 1999, 37 (16): 3215-3225
[45] Andruzzi Luisa, D'Apollo Francesca, Galli Giancarlo. Synthesis and Structure Characterization of Liquid Crystalline Polyacrylates with Unconventional Fluoroalkylphenyl Mesogens [J]. Macromolecules, 2001, 34 (22): 7707-7714
[46] Barmatov EB, Filippov AP, Shibaev VP. Side group functionalized liquid crystalline polymers and blends VIII. Nematic and SmAre phase formation in hydrogen-bonded blends of smectic side group LC polymers and a low molar mass dopant [J]. Liquid Crystals, 2001, 28 (4): 511-523
[47] Fitch John W, Payne Wyatt G, Westmoreland Donald. Platinum-catalyzed acylative cleavage of cyclic ethers [J]. Journal of Organic Chemistry, 1983, 48(5): 751-3
[48] Pri-Bar I, Stille J K. Acylative cleavage of ethers catalyzed by triorganotin halides and palladium (II) complexes [J]. Journal of Organic Chemistry, 1982, 47(7): 1215-20
[49] Commercon A, Normant JF, Villieras J. Substitution of 1-halo-alkynes by organometallic copper derivatives. Route to a new class of synthons: application to the synthesis of bombykol [J]. Tetrahedron, 1980, 36(9): 1215-21
[50] Broer, DJ, Vriens L. Laser-induced optical recording in thin films: Modeling of the hole opening and experiments with organic sublayers [J]. Applied Physics A: Solids and Surfaces, 1983, 32 (3): 107-23
[51] Broer DJ, Mol GN. Oriented polymers obtained by UV-polymerization of oriented low molecular weight species [J]. Polymeric Materials Science and Engineering, 1986, 55: 540-4
[52] Broer DJ, Gossink RG, Hikmet R. Oriented polymer networks obtained by photo polymerization of liquid-crystalline monomers [J]. Angewandte Makromolekulare Chemie , 1990, 183: 45-66
[53] Broer DJ, Heynderickx I. Three-dimensionally ordered polymer networks with a helicoidal structure. Macromolecules , 1990, 23(9): 2474-7
[54] Broer DJ, Mol GN, Challa G. Temperature effects on the kinetics of photoinitiated polymerization of dimethacrylates [J]. Polymer, 1991, 32(4): 690-5
[55] Hikmet R, Broer DJ. Dynamic mechanical properties of anisotropic networks formed by liquid-crystalline acrylates [J]. Polymer , 1991, 32(9): 1627-32
[56] Heynderickx I, Broer DJ. The use of cholesterically polymer networks in practical applications [J]. Molecular Crystals and Liquid Crystals, 1991, 203: 113-26
[57] Hikmet R, Zwerver B, Broer D. Anisotropic polymerization shrinkage behavior of liquid-crystalline diacrylates [J]. Polymer, 1992), V33(1): 89-95
[58] Broer DJ, Lub J, Mol GN. Synthesis and photopolymerization of a liquid-crystalline diepoxide [J]. Macromolecules, 1993, 26(6): 1244-7
[59] Heynderickx I, Broer DJ, Tervoort-Engelen Y. Visualization of the cholesteric texture near a Grandjean line [J]. Liquid Crystals, 1993, 15 (5): 745-8
[60] Lub J., Broer DJ, Hikmet R. Synthesis and photopolymerization of cholesteric liquid crystalline diacrylates [J]. Liquid Crystals, 1995, 18 (2): 319-26
[61] Broer DJ, Lub J, Mol GN. Wide-band reflective polarizers from cholesteric polymer networks with a pitch gradient [J]. Nature (London), 1995, 378 (6556): 467-9
[62] Lub J, Broer DJ, Antonio ME, Martinez. The formation of a liquid crystalline main chain polymer by means of photopolymerization [J]. Liquid Crystals, 1998, 24 (3): 375-79
[63] Bhar Sanjay, Ranu Brindaban C. Zinc-Promoted Selective Cleavage of Ethers in Presence of Acyl Chloride. Journal of Organic Chemistry, 1995, 60 (3): 745-7
[64] Chen H, Philip, Katsis, Chen H. Deterministic Synthesis and Optical Properties of Glassy Chiral-Nematic Liquid Crystals [J]. Chemistry of Materials, 2003, 15 (13): 2534-2542