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Monolith separation medium for chromatography and process for producing the same

a technology of chromatography and monoliths, applied in other chemical processes, instruments, transportation and packaging, etc., can solve the problems of low uniformity of structure, particle aggregation type, and low performance of monoliths based on silica gel, and achieve high performan

Inactive Publication Date: 2010-08-26
SHIMADZU CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0007]As a result of extensive studies to solve such problems, it was found by the present inventors that a porous material having an extremely uniform skeletal structure can be obtained by dissolving an epoxy compound having a specific molecular structure in a porogen; adding an amine compound of bi- or higher functionality thereto and heating them to polymerize, thereby causing the resulting polymer and the porogen to undergo spinodal decomposition; crosslinking the materials stably before they transit to a particle-aggregation structure due to the growth of phase separation, thereby freezing a non-particle-aggregation-type co-continuous structure; and subsequently removing the porogen. It was also found that the resulting porous material can serve as a separation medium which develops an extremely high theoretical plate number due to the uniformity of the skeleton thereof. As a result, the present invention has been accomplished.
[0024]The monolith separation medium of the present invention is useful as a stationary phase for liquid chromatograpy which demonstrates unprecedentedly high performance because the skeletal phase thereof has an average diameter of submicron to micrometer size, and has a non-particle-aggregation-type co-continuous structure, and is constituted of an addition polymer from an epoxy compound of bi- or higher functionality and an amine compound of bi- or higher functionality, and is enriched in an organic matter, and does not contain any carbon atoms derived from aromatic series. Moreover, it can be used for columns of general-purpose size as well as for capillary columns.
[0026]When a monolith separation medium is formed using optically active substances as both the epoxy compound and the amine compound, it becomes possible to separate the S-isomer and the R-isomer of optical antipodes with this separation medium.

Problems solved by technology

Therefore, although a through pore is formed, the structure is of low uniformity and becomes particle aggregation type.
As a result, high performance like that of monoliths based on silica gel has not been realized yet.
In such a solution system, the van der Waals force between polymer chains is basically greater than the steric hindrance of growing polymer chains, resulting in flocculation of polymer chains.
Thus, this causes generation of nuclei due to polymer chain entanglement, growth of microgel particles due to polymer chain flocculation, and rapid increase in surface energy of the system.
Therefore, such a system composed of a monomer and a poor solvent is characterized in that gel grows in the form of particle aggregation, and phase separation occurs extremely early in competition with gelation and a monolith form where macroporous pores have a small specific surface area is fixed, resulting in a particle aggregation type monolith.
Therefore, conventional monoliths have no skeletal structure and inherently have some problems, such as large maze factors of a through pore, increase in back pressure at high flow rate, and morphological change due to monolith compressibility.

Method used

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  • Monolith separation medium for chromatography and process for producing the same
  • Monolith separation medium for chromatography and process for producing the same
  • Monolith separation medium for chromatography and process for producing the same

Examples

Experimental program
Comparison scheme
Effect test

example 1

Reagents and Solvent

[0033]Used were 2,2,2-tri-(2,3-epoxypropyl)-isocyanurate (TEPIC-S), which is an optically active SSS-isomer, as epoxy compound, bis(4-aminocyclohexyl)methane (BALM) as an amine compound, and polyethylene glycol having a molecular weight of 200 (PEG200, a commercial name of Nacalai Tesque, Inc.) as a porogen.

[0034]The chemical structure formulas of TEPIC and BACM are shown below.

[Production of Polymer Monolith]

[0035]Following addition of 0.37 g of BACM and 7.00 g of PEG200 to 1.6 g of TEPIC-S, they were heated and stirred with a hot stirrer into a state where they are dissolved. Thereafter, they were filled into a fused quartz capillary tube and heated for 20 hours in a drier at 80° C. to be polymerized.

[0036]Then, the resultant was washed with water and methanol, and then dried in vacuo.

Production Conditions

[0037]

TEPIC-S1.6gBACM0.37gPEG2007.00gTemperature80°C.

[0038]A scanning electron micrograph of the organic polymer monolith capillary column produced by the abo...

example 2

[0043]By using optically active substances as both an epoxy compound and an amine compound, a chiral organic polymer monolith capillary column was produced.

[0044]An optically active SSS-isomer of 2,2,2-tri-(2,3-epoxypropyl)-isocyanurate (TEPIC-S) in an amount of 0.40 g as an epoxy compound, 0.63 g of an optically active isomer, (1S,2S)-(+)-1,2-cyclohexanediamine, and 10 g of polyethylene glycol having a molecular weight 300 (PEG300) were mixed, heated and stirred into a state where they were dissolved. Thereafter, they were filled into a fused quartz capillary tube, and heated for 4 hours in an oven at 120° C. to be polymerized.

[0045]Then, the resultant was washed with water and methanol, and then dried in vacuo.

Production Conditions

[0046]

TEPIC-S0.40g(1S,2S)-(+)-1,2-cyclohexanediamine0.63gPEG30012.64gTemperature120°C.

[0047]The organic polymer monolith of Example 2 produced by the above-mentioned polymerization was also a skeletal phase similar to that of the example 1.

[0048]A separa...

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Abstract

To obtain a non-particle-aggregation-type organic polymer monolith separation medium, there is provided a monolith separation medium comprising a skeletal phase and pores being continuous in the form of three-dimensional network, which skeletal phase on its surface has a functional group permitting introduction of a new functional group. The skeletal phase has a non-particle-aggregation-type co-continuous structure having an average diameter of submicron to micrometer size, and is constituted of an addition polymer from an epoxy compound of bi- or higher functionality and an amine compound of bi- or higher functionality. Further, the skeletal phase is enriched in organic matter and does not contain any carbon atoms derived from aromatic series.

Description

TECHNICAL FIELD[0001]The present invention relates to a monolith separation medium for chromatography having a co-continuous structure comprising a skeletal phase enriched in an organic matter and a pore being continuous in the form of three-dimensional network, and to a process for producing the same.BACKGROUND ART[0002]It is reported about porous materials called monoliths in which through flow channels and a skeleton are integrated, that advantages which have not been recognized with conventional particle-filled type columns are developed, that is, when they are used as a separation medium for high-performance liquid chromatography, high column performance is obtained due to the wide flow channels and the thin skeleton, and deterioration of the performance is inhibited even under a high flow rate due to a low pressure loss (see N. Ishizuka, H. Kobayashi, H. Minakuchi, K. Nakanishi, K. Hirao, K. Hosoya, T. Ikegami and N. Tanaka, J. Chromatogr. A, 960, 85 (2002)).[0003]Monoliths ma...

Claims

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Application Information

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IPC IPC(8): C09K3/00
CPCB01J20/26B01J20/265B01J20/28042B01J20/285B01J20/291G01N2030/528B01J20/3242B01J20/3244B01J2220/82B01J2220/84B01J20/305Y10T428/249995Y10T428/249953Y10T428/249994
Inventor HOSOYA, KEN
Owner SHIMADZU CORP
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