WO2020056795A1 - Purification method for liquid crystal material having fluoroalkoxy as end group - Google Patents

Purification method for liquid crystal material having fluoroalkoxy as end group Download PDF

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WO2020056795A1
WO2020056795A1 PCT/CN2018/108921 CN2018108921W WO2020056795A1 WO 2020056795 A1 WO2020056795 A1 WO 2020056795A1 CN 2018108921 W CN2018108921 W CN 2018108921W WO 2020056795 A1 WO2020056795 A1 WO 2020056795A1
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liquid crystal
crystal material
fluoroalkoxy
adsorbent
electric field
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黄晓
康庄
胡娟
刘钰
黄曦
陈法兵
姜志炜
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江苏和成新材料有限公司
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
    • C09K2019/301—Cy-Cy-Ph

Definitions

  • the applied electric field is an alternating electric field.
  • the liquid crystal material mixed with silica gel is put into an ion membrane purifier, and an oxide thin film electrode is used with a pole pitch of 20 mm and an electric field strength of 3 kV / cm.
  • the liquid crystal material is collected for 60 minutes and collected. The purity was 99.5% by HPLC analysis.
  • the liquid crystal material mixed with activated alumina was put into an ion membrane purifier, and an oxide thin film electrode was used with a pole spacing of 20 mm and an electric field strength of 3 kV / cm.
  • the liquid crystal material was collected for 60 minutes and collected. The purity was 99.9% by HPLC analysis.

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  • Chemical & Material Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Electrostatic Separation (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)
  • Separation Using Semi-Permeable Membranes (AREA)
  • Treatment Of Liquids With Adsorbents In General (AREA)

Abstract

The present invention provides a purification method for a liquid crystal material having fluoroalkoxy as an end group, comprising the following steps: (1) adding an adsorbent to a liquid crystal material to be purified, and mixing same uniformly; and (2) feeding the liquid crystal material mixed with the adsorbent into an ion-exchange membrane purifier, applying an external electric field, performing adsorbing for 0.5 h to 3 h, and collecting the purified liquid crystal material. The intensity of the electric field is 1 kV/cm to 10 kV/cm, and the electrode spacing is 20 mm to 50 mm. The purification method for a liquid crystal material having fluoroalkoxy as the end group according to the present invention achieves high purity, is convenient to operate, and can perform purification without using other solvents, saving costs, and being safer and more environmentally-friendly.

Description

一种端基为氟代烷氧基的液晶材料的提纯方法Purification method of liquid crystal material with fluoroalkoxy terminal group 技术领域Technical field
本发明涉及一种提纯方法，尤其是一种高沸点端烯类液晶材料的提纯方法。The invention relates to a purification method, in particular to a purification method of a high-boiling terminal olefinic liquid crystal material.
背景技术Background technique
随着显示面板对液晶材料纯度的要求越来越高，现有的提纯工艺已无法满足液晶材料超高纯度的要求。由于液晶材料的高技术壁垒，导致高纯度的中高端液晶材料市场多年来一直处于垄断状态。开发出高品质液晶单体的提纯方式势在必行。As display panels have higher and higher requirements for the purity of liquid crystal materials, the existing purification process has been unable to meet the ultra-high purity requirements of liquid crystal materials. Due to the high technological barriers of liquid crystal materials, the high-purity mid-to-high-end liquid crystal material market has been in a monopoly state for many years. It is imperative to develop a purification method for high-quality liquid crystal monomers.
液晶材料粗品除含有主要产品外，还含有微量无机杂质和大量极性有机杂质，而这些杂质主要是在液晶化合物合成过程中从原材料或仪器设备或生产环境引入，或由反应产生的副产物以及未反应的物料造成。目前有关液晶化合物的提纯方法主要有吸附法、分子蒸馏或精馏法、外加电场法、柱层析法等，这些方法虽能获得高精度的液晶产品，但是过程繁琐，提纯过程中使用的有机溶剂多数带有毒性且易燃易爆，有害健康且不利于环保，提纯后还会产生废液处理等问题，给企业带来了新的压力。In addition to the main products, the crude liquid crystal materials also contain trace inorganic impurities and a large amount of polar organic impurities, and these impurities are mainly introduced from raw materials or instruments and equipment or the production environment during the synthesis of liquid crystal compounds, or by-products produced by the reaction, and Caused by unreacted materials. At present, the purification methods of liquid crystal compounds mainly include adsorption method, molecular distillation or rectification method, external electric field method, column chromatography method, etc. Although these methods can obtain high-precision liquid crystal products, the process is cumbersome and the organic used in the purification process is complicated. Most of the solvents are toxic, flammable and explosive, harmful to health and not environmentally friendly. After purification, there will be problems such as waste liquid treatment, which brings new pressure to the enterprise.
发明内容Summary of the Invention
本发明提供了一种端基为氟代烷氧基的液晶材料的提纯方法。The invention provides a method for purifying a liquid crystal material having a fluoroalkoxy terminal group.
本发明的技术方案如下：The technical solution of the present invention is as follows:
一种端基为氟代烷氧基的液晶材料的提纯方法，包括如下步骤：A method for purifying a liquid crystal material having a fluoroalkoxy terminal group includes the following steps:
(1)向待提纯的液晶材料中添加吸附剂，混合均匀；(1) Add an adsorbent to the liquid crystal material to be purified and mix well;
(2)将混有吸附剂的液晶材料投入离子膜提纯器中，施加外加电场，吸附0.5～3h，收集提纯后的液晶材料；(2) Put the liquid crystal material mixed with the adsorbent into an ion membrane purifier, apply an external electric field, adsorb for 0.5 to 3 hours, and collect the purified liquid crystal material;
所述吸附剂选自活性氧化铝、活性炭、硅胶、沸石中的一种或多种。The adsorbent is selected from one or more of activated alumina, activated carbon, silica gel, and zeolite.
所述外加电场是交流电场。The applied electric field is an alternating electric field.
所述吸附剂的孔径为1～10nm，吸附剂的比表面积为500～1000m 2/g。 The pore diameter of the adsorbent is 1 to 10 nm, and the specific surface area of the adsorbent is 500 to 1000 m 2 / g.
所述吸附剂与液晶材料的质量比1:5～1:20。The mass ratio of the adsorbent to the liquid crystal material is 1: 5 to 1:20.
所述液晶材料在外加电场下的吸附时间为1～1.5h。The adsorption time of the liquid crystal material under an applied electric field is 1 to 1.5 h.
所述离子膜提纯器选自单一离子膜提纯器、双槽离子膜提纯器、三槽离子膜提纯器中的一种。The ion membrane purifier is selected from the group consisting of a single ion membrane purifier, a two-slot ion membrane purifier, and a three-slot ion membrane purifier.
所述提纯器的离子膜为均相阴、阳离子交换膜，电极为网式贵金属氧化物涂层电极。The ionic membrane of the purifier is a homogeneous anion and cation exchange membrane, and the electrode is a mesh-type noble metal oxide coating electrode.
所述电场强度为1kV/cm～10kV/cm，电极间距为20～50mm。The electric field strength is 1 kV / cm to 10 kV / cm, and the electrode spacing is 20 to 50 mm.
有益效果：本发明的端基为氟代烷氧基的液晶材料的提纯方法，提纯精度高，操作方便，无需使用其他溶剂即可进行，节约成本，更加安全环保。Beneficial effects: The method for purifying a liquid crystal material whose end group is a fluoroalkoxy group has high purification precision, convenient operation, can be performed without using other solvents, saves costs, and is more safe and environmentally friendly.
具体实施方式detailed description
实施例1Example 1
1.取3g含有
Figure PCTCN2018108921-appb-000001
的待提纯液晶材料，0.6g孔径和比表面积分别为4nm和600m 2/g的硅胶，混合均匀； 1. Take 3g containing
Figure PCTCN2018108921-appb-000001
Of the liquid crystal material to be purified, 0.6 g of silica gel having a pore diameter and a specific surface area of 4 nm and 600 m 2 / g, respectively, and mixed uniformly;
2.将混有硅胶的液晶材料投入到离子膜提纯器中，采用氧化物薄膜电极，极间距为20mm，电场强度为3kV/cm，保持60min，收集提纯后的液晶材料。经HPLC分析纯度为99.8％。2. The liquid crystal material mixed with silica gel is put into an ion membrane purifier, and an oxide thin film electrode is used, with a pole pitch of 20 mm, an electric field strength of 3 kV / cm, and maintained for 60 minutes. The purity was 99.8% by HPLC analysis.
实施例2Example 2
1.取3g含有
Figure PCTCN2018108921-appb-000002
的待提纯液晶材料，0.6g孔径和比表面积分别为4nm和600m 2/g的硅胶，混合均匀； 1. Take 3g containing
Figure PCTCN2018108921-appb-000002
Of the liquid crystal material to be purified, 0.6 g of silica gel having a pore diameter and a specific surface area of 4 nm and 600 m 2 / g, respectively, and mixed uniformly;
2.将混有硅胶的液晶材料投入到离子膜提纯器中，采用氧化物薄膜电极，极间距为20mm，电场强度为3kV/cm，保持60min，收集提纯后的液晶材料。经HPLC分析纯度为99.5％。2. The liquid crystal material mixed with silica gel is put into an ion membrane purifier, and an oxide thin film electrode is used with a pole pitch of 20 mm and an electric field strength of 3 kV / cm. The liquid crystal material is collected for 60 minutes and collected. The purity was 99.5% by HPLC analysis.
实施例3Example 3
1.取3g含有
Figure PCTCN2018108921-appb-000003
的待提纯液晶材料，0.6g孔径和比表面积分别为4nm和600m 2/g的活性氧化铝，混合均匀； 1. Take 3g containing
Figure PCTCN2018108921-appb-000003
Of the liquid crystal material to be purified, 0.6 g of activated alumina having a pore diameter and a specific surface area of 4 nm and 600 m 2 / g, respectively, and mixed uniformly;
2.将混有活性氧化铝的液晶材料投入到离子膜提纯器中，采用氧化物薄膜电极，极间距为20mm，电场强度为3kV/cm，保持60min，收集提纯后的液晶材料。经HPLC分析纯度为99.9％。2. The liquid crystal material mixed with activated alumina was put into an ion membrane purifier, and an oxide thin film electrode was used with a pole spacing of 20 mm and an electric field strength of 3 kV / cm. The liquid crystal material was collected for 60 minutes and collected. The purity was 99.9% by HPLC analysis.
实施例4Example 4
1.取3g含有
Figure PCTCN2018108921-appb-000004
的待提纯液晶材料，0.3g孔径和比表面积分别为4nm和600m 2/g的活性氧化铝，混合均匀； 1. Take 3g containing
Figure PCTCN2018108921-appb-000004
Of the liquid crystal material to be purified, 0.3 g of activated alumina having a pore diameter and a specific surface area of 4 nm and 600 m 2 / g, respectively, and mixed uniformly;
2.将混有活性氧化铝的液晶材料投入到离子膜提纯器中，采用氧化物薄膜电极，极间距为35mm，电场强度为5kV/cm，保持75min，收集提纯后的液晶材料。经HPLC分析纯度为99.7％。2. The liquid crystal material mixed with activated alumina was put into an ion membrane purifier, and an oxide thin film electrode was used. The electrode pitch was 35 mm, the electric field strength was 5 kV / cm, and the liquid crystal material was collected for 75 min. The purity was 99.7% by HPLC analysis.
实施例5Example 5
1.取3g含有
Figure PCTCN2018108921-appb-000005
的待提纯液晶材料，0.3g孔径和比表面积分别为4nm和600m 2/g的硅胶，混合均匀； 1. Take 3g containing
Figure PCTCN2018108921-appb-000005
Of the liquid crystal material to be purified, 0.3g of silica gel having a pore diameter and a specific surface area of 4nm and 600m 2 / g, respectively, and mixed well;
2.将混有硅胶的液晶材料投入到离子膜提纯器中，采用氧化物薄膜电极，极间距为35mm，电场强度为5kV/cm，保持75min，收集提纯后的液晶材料。经HPLC分析纯度为99.6％。2. The liquid crystal material mixed with silica gel is put into an ion membrane purifier, and an oxide thin film electrode is used. The electrode pitch is 35 mm, the electric field strength is 5 kV / cm, and the liquid crystal material is collected for 75 min. The purity by HPLC analysis was 99.6%.

Claims (8)

  1. 一种端基为氟代烷氧基的液晶材料的提纯方法，其特征在于，包括以下步骤：A method for purifying a liquid crystal material having a fluoroalkoxy terminal group, which comprises the following steps:
    (1)向待提纯的液晶材料中添加吸附剂，混合均匀；(1) Add an adsorbent to the liquid crystal material to be purified and mix well;
    (2)将混有吸附剂的液晶材料投入离子膜提纯器中，施加外加电场，吸附0.5～3h，收集提纯后的液晶材料；(2) Put the liquid crystal material mixed with the adsorbent into an ion membrane purifier, apply an external electric field, adsorb for 0.5 to 3 hours, and collect the purified liquid crystal material;
    所述吸附剂选自活性氧化铝、活性炭、硅胶、沸石中的一种或多种。The adsorbent is selected from one or more of activated alumina, activated carbon, silica gel, and zeolite.
  2. 根据权利要求1所述的端基为氟代烷氧基的液晶材料的提纯方法，其特征在于，所述外加电场是交流电场。The method for purifying a liquid crystal material whose terminal group is a fluoroalkoxy group according to claim 1, wherein the applied electric field is an AC electric field.
  3. 根据权利要求1所述的端基为氟代烷氧基的液晶材料的提纯方法，其特征在于，所述吸附剂的孔径为1～10nm，吸附剂的比表面积为500～1000m 2/g。 The method for purifying a liquid crystal material having a fluoroalkoxy terminal group according to claim 1, wherein a pore diameter of the adsorbent is 1 to 10 nm, and a specific surface area of the adsorbent is 500 to 1000 m 2 / g.
  4. 根据权利要求1所述的端基为氟代烷氧基的液晶材料的提纯方法，其特征在于，所述的吸附剂与液晶材料的质量比1:5～1:20。The method according to claim 1, wherein the mass ratio of the adsorbent to the liquid crystal material is 1: 5 to 1:20.
  5. 根据权利要求1所述的端基为氟代烷氧基的液晶材料的提纯方法，其特征在于，所述液晶材料在外加电场下的吸附时间为1～1.5h。The method for purifying a liquid crystal material having a fluoroalkoxy terminal group according to claim 1, wherein an adsorption time of the liquid crystal material under an applied electric field is 1 to 1.5 h.
  6. 根据权利要求2所述的端基为氟代烷氧基的液晶材料的提纯方法，其特征在于，所述提纯器选自单一离子膜提纯器、双槽离子膜提纯器、三槽离子膜提纯器中的一种。The method for purifying a liquid crystal material having a fluoroalkoxy terminal group according to claim 2, characterized in that the purifier is selected from the group consisting of a single ion membrane purifier, a two-slot ion membrane purifier, and a three-slot ion membrane purifier. Device.
  7. 根据权利要求2所述的端基为氟代烷氧基的液晶材料的提纯方法，其特征在于，所述提纯器的离子膜为均相阴、阳离子交换膜，电极为网式贵金属氧化物涂层电极。The method for purifying a liquid crystal material having a fluoroalkoxy terminal group according to claim 2, wherein the ionic membrane of the purifier is a homogeneous anion and cation exchange membrane, and the electrode is a net-type precious metal oxide coating. Layer electrode.
  8. 根据权利要求1或2所述的端基为氟代烷氧基的液晶材料的提纯方法，其特征在于，所述电场强度为1kV/cm～10kV/cm，电极间距为20～50mm。The method for purifying a liquid crystal material having a fluoroalkoxy terminal group according to claim 1 or 2, wherein the electric field strength is 1 kV / cm to 10 kV / cm, and the electrode pitch is 20 to 50 mm.
PCT/CN2018/108921 2018-09-20 2018-09-30 Purification method for liquid crystal material having fluoroalkoxy as end group WO2020056795A1 (en)

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