WO1997030349A1 - Element de colonne de chromatographie liquide et procede de production associe - Google Patents

Element de colonne de chromatographie liquide et procede de production associe Download PDF

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Publication number
WO1997030349A1
WO1997030349A1 PCT/JP1997/000339 JP9700339W WO9730349A1 WO 1997030349 A1 WO1997030349 A1 WO 1997030349A1 JP 9700339 W JP9700339 W JP 9700339W WO 9730349 A1 WO9730349 A1 WO 9730349A1
Authority
WO
WIPO (PCT)
Prior art keywords
resin
column
porous
glass support
porous glass
Prior art date
Application number
PCT/JP1997/000339
Other languages
English (en)
Japanese (ja)
Inventor
Kumiko Maekawa
Akira Tamaki
Tomoaki Nakanishi
Original Assignee
Nippon Fusso Co., Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nippon Fusso Co., Ltd. filed Critical Nippon Fusso Co., Ltd.
Publication of WO1997030349A1 publication Critical patent/WO1997030349A1/fr

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Classifications

    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
    • G01N30/02—Column chromatography
    • G01N30/60—Construction of the column
    • G01N30/6047—Construction of the column with supporting means; Holders
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
    • G01N30/02—Column chromatography
    • G01N30/60—Construction of the column
    • G01N30/6052—Construction of the column body

Definitions

  • a mobile phase in which a plurality of solutes is dissolved is passed through a mobile phase in which a plurality of solutes are dissolved in a column packed with a stationary phase.
  • Liquid chromatography used for liquid chromatography that separates and analyzes solutes by physical or chemical interaction between the phase and the stationary phase It relates to the roughing column elements and the method of manufacturing them.
  • LCs Liquid chromatographs
  • HPLC high-speed liquid chromatography
  • SUS stainless steel
  • PEEK terketone
  • a carrier consisting of a silica gel powder or a porous glass powder and a polymer [N] having a chemical bond to the carrier are used.
  • the heat of the tetrafluoroethylene copolymer (PFA) is added to the rod-shaped support formed from the material and the tetrafluoroethylene resin. Put the shrink tubing over it and heat shrink it to form the outer skin, and then apply water pressure from the surrounding area. Wear is not the mosquito ram for HPLC is that has been known (JP-open Akira 6 3 - 2 0 0 0 6 0 Patent Gazette).
  • HPLC columns are not damaged even under a pressure of (l) 200 kgf / cm 2 , and do not break down and leak the analyte solution.
  • the analyte solution is contaminated with dissolved ions or foreign substances, because a gap is generated between the carrier and the outer membrane and the analyte solution does not short-pass.
  • the method of filling the porous glass powder into the pipe is not stable because the gap between the particles of the powder is not stable, and depending on the shape of the particles and the way of filling.
  • powder may move, and stable resolution cannot be obtained.Filling work is extremely difficult, and expensive filling is also difficult.
  • the problem is that the cost is high due to the necessity of equipment.
  • the method of forming a skin using a heat-shrinkable tube in the method is as follows.
  • the analyte is subjected to high pressure (200 kgf). / cm 2 ), the particles do not move, uniform holes can be used stably, and the resolution can be improved (the target theoretical plate number is 600,000 steps). ) It has been improved in that it can be done.
  • the outer membrane and the support are not used. May cause a leak due to the formation of a gap between the sample and the residual catalyst of the tube and the residual unreacted monomer in the analyte. There are issues that need to be resolved, such as where there is a risk of elution.
  • the method of forming the outer membrane of the porous material is not limited to the method described above, and the surface of the porous material is formed on the surface of the porous material.
  • a method of coating and impregnating the above resin composition to form an outer skin layer is also a well-known method.
  • This resin impregnation method is originally used for protecting the outer surface or strengthening the inside of the porous material, and the state of the inner surface of the resin coating layer is changed. Applying to a column support for HPLC, which is more important than the external surface condition, makes it difficult to control the impregnation uniformly. This was considered to be difficult because the point and the surface condition of the resin layer formed in the porous part could not be predicted.
  • the present invention relates to a porous porous glass support having a columnar shape, and a polyether ether kettle formed on a side surface of the porous porous glass support.
  • Resin (PEEK) resin layer and the resin layer is formed on the inner surface of the side surface of the porous resin support.
  • the resin impregnation and the porous resin support are carried out. It consists of an outer skin layer formed on the outer side of the body, and is characterized by a continuous resin-impregnated layer and outer skin layer.
  • the thickness of the resin layer is preferably 100 to 500 m, and the thickness of the resin-impregnated layer is 10 to 50 m. Is preferred.
  • the present invention also relates to a liquid chromatograph column having a sheath layer provided around the above-mentioned column element.
  • the present invention further provides a method of immersing a columnar porous porous glass support in a PEEK resinous liquid composition, and allowing the resinous liquid composition to be immersed in the PEEK resinous liquid composition.
  • the present invention relates to a method for producing the above-mentioned column element, which is characterized by being impregnated on a side surface of a body and then baked.
  • the resulting liquid composition can be used.
  • This resinous liquid composition is composed of PEEK (A) and grease.
  • the weight ratio of the call type organic liquid (B) is ⁇ ⁇ ⁇ ⁇ ⁇ /, and the solid film strength stimulant for the combined measurement of ( ⁇ ) and ( ⁇ ). It is preferable that the added amount of (C) is 0.1 to 30% by weight.
  • the average particle diameter of the solid component (PEEK and the solid film strengthening agent) in the resin liquid composition is in any case the pore diameter of the porous glass support. It is preferred that they are larger.
  • solid film strengthening agent examples include potassium titanate whisker or tetrafluoroethylenino. ⁇
  • PFA powdery vinyl alcohol vinyl copolymer
  • FIG. 1 is a schematic vertical sectional view of one embodiment of the column element of the present invention.
  • FIG. 2 is a schematic cross-sectional view of one embodiment of a column element of the present invention.
  • FIG. 3 is a scanning electron micrograph (1200 magnifications) of a portion of the column element prepared in Example 1 of the present invention, and is indicated by D in FIG. Equivalent to a minute.
  • BEST MODE FOR CARRYING OUT THE INVENTION The column element of the present invention is formed on a columnar porous glass support and on the side of the porous glass support. It is based on the resin layer of PEEK.
  • the porous glass support is produced by a zolgel method from a hydrolyzate of a metal anorecoxide such as tetraethoxysilane.
  • a metal anorecoxide such as tetraethoxysilane.
  • the porous glass support has a columnar shape, a spherical shape, a plate shape, or the like, but in the present invention, the one formed into a cylindrical shape is used. .
  • the porous glass support is a material having excellent heat resistance, thermal shock resistance, mechanical strength, acid resistance, organic solvent resistance, and microbial contamination resistance. Two 0 ⁇ ⁇ !
  • the diameter of the pores can be freely designed within a wide range of ⁇ 20 // m.The control can be done, and the distribution of the pore diameters is extremely sharp. It is a thing.
  • the porosity can also be controlled arbitrarily, but usually a porosity of 20-65% is used as a column element for LC or HPLC. Is appropriate.
  • the cylindrical porous glass support used in the present invention has a diameter of about 2 mm x a length of about 50 111 111 to a diameter of about 20 111 111 and a length of about 300 mm
  • the average pore diameter is in the range of about 2 m or less.
  • the column element of the present invention is composed of a PEEK resin layer 2 on the side surface of the cylindrical porous porous glass support 1.
  • the resin layer 2 has a resin-impregnated layer 3 and a porous layer formed on the inner surface of the side surface of the porous porous glass support 1. It consists of a skin layer 4 formed on the outside of the side surface of the glass support 1, and these impregnated layers and the skin layer are continuous. is there .
  • the relationship between the resin layer and the porous glass support is described by a longitudinal sectional view (D in FIG. 1) of the column element of the present invention produced in Example 1 described later. Can be observed with a scanning electron micrograph (Fig. 3. 120,000 times) of Fig. 3.
  • 1 is a multi-hole.
  • This is a glass support
  • -2 is a resin layer of PEEK.
  • the resin layer 2 is partially impregnated into the inner part of the porous glass support 1 to form the impregnated layer 3
  • the outer skin layer is formed on the outer part of the support 1. 4 is formed.
  • the impregnated layer 3 and the outer skin layer 4 form a continuous phase.
  • PEEK which forms this resin layer, has excellent heat resistance, mechanical toughness, and chemical resistance, and can be obtained with high purity. It has traditionally been used in the fields of analytical chemistry and biochemistry. However, in the field of LC and HPLC columns, as described above, the column material is a pipe material equivalent to a container for filling the column with the powder. It was only used for this purpose, and in its usage form, it had the above-mentioned problem.
  • the thickness of the PPEK resin layer should be selected within the range of 100 to 500 ⁇ m, preferably within the range of 200 to 400 // m. As the thickness increases, the diameter of the column element increases, and the diameter of the column element is reduced to reduce the diameter of the column to be loaded into the spigot device. If it is too thin, it will not be able to withstand the pressure (up to approximately 200 kgf / cm 2 ) applied during the analysis, and the column may break. There is.
  • the thickness of the impregnated layer is preferably from 10 to 50 / m, particularly preferably from 20 to 40 im.
  • the effective area of the glass layer (solid phase) is reduced, and the analysis efficiency is reduced.
  • the resin layer is too thin, the resin outer layer is connected to the porous glass support. Insufficient integration may result in liquid leakage.
  • the column element of the present invention is inserted into a protective PFA tube and fixed with a stainless steel base. By doing so, you can create an LC or HPLC system.
  • the solid phase is not composed of particles, the particles can be moved even when the analyte is passed at high pressure. It is possible to stably use a uniform hole without any heat, and to improve the resolving power and the resolving power.
  • the PEK resin having high purity and high chemical resistance is in contact with the analyte solution as an impregnation layer, the analyte solution is not contaminated.
  • the impregnated layer is continuous with the outer skin layer, there is no gap between the outer skin layer and the stationary phase, and a leak of the analyte solution is generated. There is no
  • the column element of the present invention has a structure in which a columnar porous porous glass support is immersed in a resinous liquid composition of PEEK, and the resinous liquid composition is converted into a porous liquid composition. It can be manufactured by impregnating and adhering to the side surface of the glass support and then sintering.
  • the PEEK resin liquid composition that can be suitably used in the present invention includes:
  • A Polyetheretherketone (PEEK)
  • B Glycol-based organic liquid
  • PEEK has mechanical strength, heat resistance, and shochu.
  • the solid film strengthening agent is combined to improve the mechanical strength of PEEK and to alleviate the shrinkage force generated during cooling after calcination.
  • fluorocarbon resins such as potassium titanate whiskers, PFA, graphite, carbohydrated gaymen, aluminum, aluminum, and america
  • powders such as silica and oxidized titanium, discs or fibers, various kinds of ceramic fibers, etc., are exposed.
  • Titanic acid has the advantage that it has good dispersibility in resin and has a high aspect ratio, so that a small amount of addition can increase the mechanical strength. Carriage whiskers are good.
  • PFA which has high chemical resistance and is heat resistant even at the melting point of PEEK, is preferred in terms of relaxation of stress.
  • PFA various kinds of materials can be used, for example, DFA's PFA340 (Melt flow rate: 2 to 10 g). No. 10 minutes) is suitable.
  • commercially available PFA powder coatings such as MP-10 manufactured by Mitsui Dupont Chemical Co., Ltd.
  • enamels water-based
  • What is contained in the paint for example, 500 CL manufactured by Mitsui DuPont Fluorochemicals Canole Co., Ltd.
  • 500 CL manufactured by Mitsui DuPont Fluorochemicals Canole Co., Ltd.
  • the solid component (PEEK, solid film strengthening agent) in the composition is not reduced from the point that the solid phase area is not reduced. It is desirable that the particle size is substantially larger than the pore size of the porous glass support.
  • the pore size of the porous porous glass support may be larger than the solid component particle size, but may be acceptable for practical use. .
  • the particle size of the solid component is about 2 im or more, preferably about 3 m or more.
  • the upper limit is about 50; tim, and preferably about 30 um, from the viewpoint of film formability.
  • solid components include columnar and irregular shapes in addition to spherical ones, and the particle size according to the present invention is defined by the pore electrical resistance method described later. The value obtained by measuring with a degree distribution measuring instrument (for example, a Nikko Co., Ltd. Coalter Counter Multisizer 1-pi type). .
  • the particle diameter of the solid component is larger than about 2 m, especially 3 / m or more. It is preferred that
  • the particle size distribution of the solid component is narrow, since a pinhole does not occur and a dense film is formed.
  • the particle size distribution 99.9% of the particles fall within the range of 2; zm or more and 50 m or less, especially 3 im or more and 30 zm or less, as viewed from the volume distribution. I like it.
  • the PEEK resin liquid composition used in the present invention contains the above-mentioned PEEK (A) and the solid film strengthening agent (C), and a glycol-based organic liquid.
  • This glycol-based organic liquid serves not only as a dispersion medium for solid components, but also as a solvent for PEEK and the solid until the PEEK is melted during the firing of the coating film. It has the function of retaining the agent.
  • Glycol-based organic liquids are oxidatively decomposed at the calcination temperature (usually 380 to 420 ° C), and no residue remains.
  • glycol-based organic liquid examples include propylene glycol, dipropylene glycol, and ethylene glycol.
  • Monoethyl ether, polyethylene glycol monoethyl ether, 2—butoxy ethanol, 2— (2—butoki (E.g.) Ethanol, polyethylene glycol, ethylene glycol monoester, etc. are available. Of these, no residue from oxidation decomposition remains and the boiling point is high. Preferable callers are preferred.
  • the mixing ratio of each component is such that the weight ratio of the PEEK (A) Z glycol-based organic liquid (B) is 1/99 to 50/50, In particular, 20 Z80 to 25/75 is preferred.
  • A Z glycol-based organic liquid
  • the amount of the component (B) is too large, the film thickness is thin, but the film thickness is too small, and pinholes are easily generated.
  • A If the amount of the component is large, the thickness of the film varies, and cracks are easily generated after the calcination.
  • the solid film strengthening agent of the solid component is 1 to 30% by weight, preferably 1 to 5% by weight, based on the total weight of (A) and (B). This is preferred because of the uniform variance. (C) If the amount of the component is too small, the reinforcing effect becomes small, and if the component is too large, the film itself becomes a porous material.
  • Additives such as (A :), (B), and (C) components, defoamers, extenders, and the like may be added to the resinous liquid composition to impair the effects of the present invention. It can be added in a range that is unknown.
  • the power ram element of the present invention is obtained by impregnating and adhering such a resinous liquid composition to the side surface of a porous glass support by immersion and sintering. Manufactured.
  • a coating method there are generally a dip coating method, a spray coating method, an electrostatic coating method, a spin coating method, a low-temperature spray coating method, and the like.
  • a coating method there are generally a dip coating method, a spray coating method, an electrostatic coating method, a spin coating method, a low-temperature spray coating method, and the like.
  • the impregnation by the immersion method is not used, a favorable result that the film thickness becomes uniform cannot be obtained.
  • the impregnation and impregnation of the PEEK resin onto the porous glass support by the immersion method of the present invention is preferably carried out by, for example, the sputum method. It is better.
  • the upper end is open in the depressurization chamber, which is configured so that the porous support can move up and down in an airtight state, and the upper end is open.
  • a coating tank in which the liquid composition is stored is arranged, and the inside of the decompression chamber is depressurized to release air from the porous glass support.
  • the body is immersed in the liquid composition in the coating tank, the inside of the depressurizing chamber is returned to the atmospheric pressure, and then removed from the depressurizing chamber through the coating tank and removed.
  • the porous resin support impregnated with the resin is calcined.
  • Immersion ⁇ of the decompression is usually 7 5 ⁇ 7 0 0 mm H g, good or to rather than the 4 5 0 ⁇ 5 5 0 mm H not good if Re to hold to g.
  • the time for infiltrating the porous glass support into the resinous liquid composition is usually 1 to 60 seconds, preferably 5 to 10 seconds. If too short, the impregnation may be insufficient, and if too long, the resin will penetrate deeply into the porous glass support.
  • the support impregnated with the resin removed from the decompression chamber is dried, if necessary, and then fired.
  • the calcination is usually above the melting point of PEEK (334 ° C), preferably between 38 and 420 minutes and longer than 30 minutes, preferably between 30 and 60 minutes. Do it by keeping it.
  • PG propylene glycol
  • Fig. 3 shows a scanning electron micrograph (magnification: 1200 times) of the side surface of column element No. 2 (the magnification of Fig. 3 has been described above). ).
  • the column element No.:! ⁇ 3 is inserted into a PFA heat-shrinkable tube with an inner diameter of 7 mm, heat-contracted by hot air, and the column element is densely packed. After being attached, the end was fixed with a stainless steel connection base to make a column for HPLC.
  • Example 1 The PEEK, propylene glycol (PG), potassium titanate whisker and porous glass support used in Example 1 were used. ,? Let £ 5 1 ⁇ /? 0 be 22-78, and the amount of potassium titanate whisker added to PEEK is 0% by weight, 1% by weight, and 2% by weight. % And 5% by weight, a PEEK resin liquid composition was prepared in the same manner as in Example 1, and the composition was applied to a porous glass support. In the same manner as in Example 1, the elements were impregnated and adhered by the immersion method, and calcined to produce column elements (Nos. 4 to 7).
  • PFA paint (Dupont PFA340 dispersed in water; 500 CL manufactured by Mitsui Dupont Chemical Co., Ltd.) was mixed with the same PEEK used in Example 1, and the propylene glycol was added as an organic liquid to the PEEK organic liquid (weight ratio).
  • a PEEK resin liquor composition was prepared in the form of an enamel paint in which PFA was triple i% of PEEK, which was blended so as to be 22-78.
  • Example 1 Using this composition, a column element was produced in the same manner as in Example 1, and observed with a scanning electron microscope in the same manner as in Example 1.
  • the surface state of the resin layer of Example 1 was free of pinhole cracks, the thickness of the resin layer was uniform at 320 im, and the thickness of the impregnated layer was 31 It was ⁇ ⁇ .
  • the column element of the present invention under the pressure of 200 kgf / 'cm required for a liquid chromatography column. There is no damage, no leakage of the analytical solution and no generation of interstices, and no leakage.
  • the analytical solution is not contaminated with dissolved ions or foreign substances.
  • the column of the present invention is distinguished by the use of the stable and uniform pores of a porous glass support (non-powder) support.
  • the resolution target number of theoretical plates: 600,000

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  • Physics & Mathematics (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Analytical Chemistry (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Immunology (AREA)
  • Pathology (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)
  • Treatment Of Liquids With Adsorbents In General (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

Cet élément de colonne, destiné à une colonne de chromatographie liquide, comprend un support cylindrique en verre poreux sur lequel on a formé une couche de résine à base de polyéther éther cétone, cette couche se composant d'une couche imprégnée de résine, formée sur le côté intérieur du support et d'une couche extérieure de placage, formée sur le côté extérieur du support, la couche imprégnée étant formée en continu avec la couche extérieure de placage. On décrit également une colonne dans laquelle on utilise cet élément que l'on produit en plongeant le support cylindrique en verre poreux dans la composition de résine à base de polyéther éther cétone, de manière à ce que la surface latérale dudit support soit imprégnée de cette composition de résine, puis en cuisant ledit support. Cette colonne ne présente pas de trajectoire courte, de fuite ni de fuite d'impuretés lorsqu'on l'utilise pour une chromatographie en phase liquide sous haute pression et elle permet d'effectuer une haute résolution.
PCT/JP1997/000339 1996-02-15 1997-02-07 Element de colonne de chromatographie liquide et procede de production associe WO1997030349A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP8/27547 1996-02-15
JP8027547A JP2000002697A (ja) 1996-02-15 1996-02-15 液体クロマトグラフィ用カラムとその製造方法

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6385689B1 (en) 1998-02-06 2002-05-07 Analog Devices, Inc. Memory and a data processor including a memory
WO2003005019A1 (fr) * 2001-07-06 2003-01-16 Api Corporation Procede permettant de determiner un sel metallique pyrithione
JP2005531011A (ja) * 2002-06-26 2005-10-13 テレダイン・イスコ・インコーポレーテッド 分離システム、分離システム構成要素及びそれらの製造方法
JP2007199041A (ja) * 2005-05-24 2007-08-09 Hellermann Tyton Co Ltd カートリッジカラム

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1318595B1 (it) * 2000-06-23 2003-08-27 Ausimont Spa Microsfere di copolimeri termoprocessabili del tetrafluoroetilene.
JP2008102077A (ja) * 2006-10-20 2008-05-01 Hellermann Tyton Co Ltd カートリッジカラムおよびカラムモジュール
FR2993666B1 (fr) 2012-07-19 2015-03-27 Commissariat Energie Atomique Procede de fabrication d'une colonne d'enrichissement de chromatographie
FR2993665B1 (fr) * 2012-07-19 2015-10-16 Commissariat Energie Atomique Procede de fabrication d'une colonne d'analyse de chromatographie

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS549691A (en) * 1977-06-22 1979-01-24 Pilot Precision Column for chromatography
JPH02291963A (ja) * 1989-05-02 1990-12-03 Matsunami Glass Kogyo Kk 多孔質ガラスを封入したガラス筒及びその封入方法

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS549691A (en) * 1977-06-22 1979-01-24 Pilot Precision Column for chromatography
JPH02291963A (ja) * 1989-05-02 1990-12-03 Matsunami Glass Kogyo Kk 多孔質ガラスを封入したガラス筒及びその封入方法

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6385689B1 (en) 1998-02-06 2002-05-07 Analog Devices, Inc. Memory and a data processor including a memory
WO2003005019A1 (fr) * 2001-07-06 2003-01-16 Api Corporation Procede permettant de determiner un sel metallique pyrithione
JP2005531011A (ja) * 2002-06-26 2005-10-13 テレダイン・イスコ・インコーポレーテッド 分離システム、分離システム構成要素及びそれらの製造方法
JP4721702B2 (ja) * 2002-06-26 2011-07-13 ダイオネックス・コーポレーション 分離システム、分離システム構成要素及びそれらの製造方法
JP2007199041A (ja) * 2005-05-24 2007-08-09 Hellermann Tyton Co Ltd カートリッジカラム

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