Monolith separation medium for chromatography and process for producing the same

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.

1 . An organic macromolecular gel-like monolith separation medium for chromatography comprising:
 a skeletal phase;   a pore formed by the skeletal phase and being continuous in the form of three-dimensional network; and   a functional group present on the surface of the skeletal phase and permitting introduction of a new functional group,   wherein the skeletal phase has an average diameter of submicron to micrometer size, has a non-particle-aggregation-type co-continuous structure, is constituted of an addition polymer from an epoxy compound of bi- or higher functionality and an amine compound of bi- or higher functionality, is enriched in an organic matter, and does not contain any carbon atom derived from aromatic series.   
     
     
         2 . The monolith separation medium according to  claim 1 , wherein the epoxy compound is 2,2,2-tri-(2,3-epoxypropyl)-isocyanurate. 
     
     
         3 . The monolith separation medium according to  claim 1 , wherein a separation column for high-performance liquid chromatography comprising the separation medium has 50000 or more theoretical plates per meter of column length. 
     
     
         4 . The monolith separation medium according to  claim 1 , wherein both the epoxy and amine compounds are optically active substances, and the separation medium has a separation ability for optical antipodes. 
     
     
         5 . A process for producing the monolith separation medium according to  claim 1 , comprising the steps of:
 (A) a step of heating an epoxy compound of bi- or higher functionality and an amine compound of bi- or higher functionality within a range of from 60 to 200° C. in a porogen to polymerize them to obtain a gel-like material,   (B) then a step of washing the gel-like material with a solvent to remove the porogen to leave the skeletal phase, and   (C) then a step of drying.   
     
     
         6 . The process for producing a monolith separation medium according to  claim 5 , wherein the epoxy compound is 2,2,2-tri-(2,3-epoxypropyl)-isocyanurate. 
     
     
         7 . The process for producing a monolith separation medium according to  claim 5 , wherein
 the amine compound is an aliphatic amine such as ethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, iminobispropylamine, bis(hexamethylene)triamine, 1,3,6-trisaminomethylhexane, polymethylenediamine, trimethylhexamethylenediamine and polyether diamine, or an alicyclic polyamine such as isophoronediamine, menthanediamine, N-aminoethylpiperazine, 3,9-bis(3-aminopropyl)2,4,8,10-tetraoxaspiron, bis(4-aminocyclohexyl)methane, cyclohexanediamine and a modified product thereof, or an aliphatic polyamidoamines composed of a polyamine and a dimmer acid.   
     
     
         8 . The process for producing a monolith separation medium according to  claim 5 , wherein optically active substances are used as both the epoxy and amine compounds. 
     
     
         9 . The process for producing a monolith separation medium according to  claim 5 , wherein the porogen is a cellosolve such as methyl cellosolve and ethylcellosolve, an ester such as ethylene glycol monomethyl ether acetate and propylene glycol monomethyl ether acetate, or a glycol such as polyethylene glycol and polypropylene glycol. 
     
     
         10 . The process for producing a monolith separation medium according to  claim 9 , wherein the porogen is polyethylene glycol. 
     
     
         11 . The monolith separation medium according to  claim 1 , wherein the epoxy compound is 2,2,2-tri-(2,3-epoxypropyl)-isocyanurate, and the amine compound is bis(4-aminocyclohexyl)methane. 
     
     
         12 . The monolith separation medium according to  claim 4 , wherein the epoxy compound is 2,2,2-tri-(2,3-epoxypropyl)-isocyanurate, and the amine compound is (1S,2S)-(+)-1,2-cyclohexanediamine. 
     
     
         13 . The process for producing a monolith separation medium according to  claim 5 , wherein the epoxy compound is 2,2,2-tri-(2,3-epoxypropyl)-isocyanurate, and the amine compound is bis(4-aminocyclohexyl)methane. 
     
     
         14 . The process for producing a monolith separation medium according to  claim 8 , wherein the epoxy compound is 2,2,2-tri-(2,3-epoxypropyl)-isocyanurate, and the amine compound is (1S,2S)-(+)-1,2-cyclohexanediamine.