Citation: SHEN Shuchang, CAI Junyang, WANG Lihong. Synthesis, Characterization and Chromatographic Performance of Schiff-base Type Silicone Polyurethane Liquid Crystal Polymer[J]. Chinese Journal of Applied Chemistry, ;2016, 33(9): 1085-1092. doi: 10.11944/j.issn.1000-0518.2016.09.150410 shu

Synthesis, Characterization and Chromatographic Performance of Schiff-base Type Silicone Polyurethane Liquid Crystal Polymer

1.
Analytical and Testing Center of Qiqihar University, Qiqihar, Heilongjiang 161006, China

Corresponding author: SHEN Shuchang,
Received Date: 23 November 2015
Available Online: 30 March 2016
Fund Project:

A new kind of small molecule Schiff base liquid crystal unit, p-phenylene(p-styrene acrylic oxo alcohol)imine was synthesized using hydroxybenzaldehyde, 3-chloropropanol, p-phenylenediamine as raw meterials. Schiff base type silicone polyurethane liquid crystal polymer was synthesized by the liquid crystal unit, 1,4-phenylene diisocyanate and 1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane. The construction of liquid crystal unit and the silicone liquid crystalline polymer were characterized by Fourier transform infrared spectrometry. The crystal structures of the liquid crystal unit and the Schiff base type silicone polyurethane liquid crystal polymer liquid crystal were identified by X-ray diffraction. The liquid crystal phase and phase transition temperature of the Schiff base type silicone polyurethane liquid crystal polymer were investigated by differential scanning calorimetry. The phase change process and optical properties of the liquid crystal material were observed by polarizing optical microscope. The chromatography column was made using Schiff base type silicone polyurethane liquid crystal polymer as stationary phase. The relative polarity of stationary liquid and the chromatographic separation performance for substituted benzene isomers were determined. Liquid crystal temperature ranges of the liquid crystal polymer are 103~146℃. It belongs to strongly polar stationary liquid(P_x=79), the separation degree of the chromatographic peaks are 0.96~3.33.
1. [1]
  [1] FU Ruonong.Evolution of Gas Chromatographic Stationary Phases[J].Chem Reag,2006,28(1):11-15(in Chinese).傅若农.气相色谱固定相的演变[J].化学试剂,2006,28(1):11-15.
2. [2]
  [2] Shillcock I M,Gareth J Price.Interactions of Solvents with Low Molar Mass and Side Chain Polymer Liquid Crystals Measured by Inverse Gas Chromatography[J].J Phys Chem B,2004,108(42):16405-16414.
3. [3]
  [3] Kuvshinova S A,Burmistrov V A,Fokina D S.Thermodynamic Properties and Selectivity of Substituted Liquid-Crystal Formylazobenzenes as Stationary Phases for Gas Chromatography[J].J Anal Chem,2009,64(5):505-508.
4. [4]
  [4] Jensen J,Grundy S C,Bretz S L.Synthesis and Characterization of Self-Assembled Liquid Crystals:p-Alkoxybenzoic Aids[J].J Chem Educ,2011,88:1133-1136.
5. [5]
  [5] Ghanem E,Al-Hariri S.Separation of Isomers on Nematic Liquid Crystal Stationary Phases in Gas Chromatography:A Review[J].Chromatographia,2014,77(9):653-662.
6. [6]
  [6] Jana R N,Cho J W.Synthesis and Characterization of Polyurethane-based Side-chain Cholesteric Liquid Crystal Polymers[J].Fibers Polym,2009,10(5):569-575.
7. [7]
  [7] Dahmane M,Athman F,Sebih S.Comparison of Analytical Properties of Two Liquid Crystalline Stationary Phases by Capillary GC[J].Chromatographia,2009,70(3/4):489-495.
8. [8]
  [8] Cook A G,Inkster R T,Martinez-Felipe A.Synthesis and Phase Behaviour of a Homologous Series of Polymethacrylate-based Side-chain Liquid Crystal Polymers[J].Eur Polym J,2012,48(4):821-829.
9. [9]
  [9] TANG Xinde,ZHAO Jun,YANG Tianzhu.Application of Radial Liquid Crystalline Macromolecules as Stationary Phase of Capillary GC[J].Anal Instrum,2001,(3):34-37(in Chinese).唐新德,赵军,杨天祝.星形大分子液晶在毛细管柱气相色谱分析中的应用研究[J].分析仪器,2001,(3):34-37.
10. [10]
  [10] TANG Xinde,ZHANG Qizhen,ZHU Minggang,et al.Preparation and Chromatographic Characteristics of the Stationary Phase for Cholesteric Ester Side Chain Polyslioxane Liquid Crystallnie[J].Chem Anal Meter,2002,11(1):38-39(in Chinese).唐新德,张其震,朱鸣刚,等.胆甾酯侧链聚硅氧烷液晶固定相的制备与色谱性能[J].化学分析计量,2002,11(1):38-39.
11. [11]
  [11] LI Ying,ZHANG Guangcheng,HU Lingfeng,et al.Synthesis and Characterization of Smectic Side-Chain Liquid Crystalline Polysiloxanes[J].J Funct Polym,2011,24(2):211-216(in Chinese).李颖,张广成,胡灵峰,等.近晶型聚硅氧烷侧链液晶的合成与表征[J].功能高分子报,2011,24(2):211-216.
12. [12]
  [12] LIN Weijiang,HUANG Kelin,WANG Zefen,et al.Research and Development of Liquid Crystalline Polyurethanes[J].Technol Dev Chem Ind,2010,39(10):20-26(in Chinese).林卫江,黄科林,王则奋,等.聚氨酯高分子液晶的研究进展[J].化工技术与开发,2010,39(10):20-26.
13. [13]
  [13] HE Shangjin,SONG Moudao,ZHANG Banghua,et al.Synthesis and Characterization of Schiff Base Type Liquid Crystal Polyurethane[J].Ion Exch Adsorpt,1999,15(2):109-114(in Chinese).何尚锦,宋谋道,张邦华.西佛碱型液晶聚氨酯的合成及表征[J].离子交换与吸附,1999,15(2):109-114.
14. [14]
  [14] Mohammed Ali.Gas Chromatographic Separation of Phenol Derivatives by Schiff-Base Liquid Crystalline Stationary Phases[J].Turk J Chem,2003,27(2):259-264.
15. [15]
  [15] YANG Ning,GAO Jianfeng,YANG Lina,et al.Synthesis and Characterization of Star-shaped Schiff Base Liquid CrystalCompounds Cntred at Silicon[J].Chem New Mater,2014,42(4):156-158(in Chinese).杨宁,高建锋,杨丽娜,等.一种以硅为中心的星型席夫碱液晶化合物的合成与表征[J].化工新型材料,2014,42(4):156-158.
16. [16]
  [16] HE Xiangdong,JIA Xudng,DING Xia,et al.Synthesis and Properties of Main Chain Liquid Crystalline Polyurethane Polyurethane[J].Acta Polym Sin,1996,(3):304-309(in Chinese).何向东,贾叙东,丁霞,等.主链型液晶聚硅氧烷聚氨醋的合成及性质[J].高分子学报,1996,(3):304-309.
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沈阳化工大学材料科学与工程学院沈阳 110142