# US 8,465,669 B2 · Monolith separation medium for chromatography and process for producing the same > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 8,465,669 B2 - Document ID: US8465669B2 - Status: Granted - Kind: B2 - Application number: 13/197,747 - Filed: 2011-08-03 - Published: 2011-11-24 - Granted: 2013-06-18 - Earliest claimed: 2011-08-03 - Assignees: Shimadzu Corporation - Applicants: Ken Hosoya - Inventors: Ken Hosoya - Web page: https://patentgrep.com/patent/US8465669B2 ## CPC - B01J 20/285: based on polymers - B01J 20/26: Synthetic macromolecular compounds - B01J 20/265: {modified or post-treated polymers (polymer carriers or substrates subjected to further impregnating or coating B01J20/3208)} - B01J 20/28042: {Shaped bodies; Monolithic structures} - B01J 20/291: Gel sorbents - B01J 20/305: {Addition of material, later completely removed, e.g. as result of heat treatment, leaching or washing, e.g. for forming pores} - B01J 20/3242: {Layers with a functional group, e.g. an affinity material, a ligand, a reactant or a complexing group} - B01J 20/3244: {Non-macromolecular compounds} - B01J 2220/82: Shaped bodies, e.g. monoliths, plugs, tubes, continuous beds - B01J 2220/84: Capillaries - G01N 2030/528: {Monolithic sorbent material} - Y10T 428/249953: Composite having voids in a component [e.g., porous, cellular, etc.] - Y10T 428/249994: Composite having a component wherein a constituent is liquid or is contained within preformed walls [e.g., impregnant-filled, previously void containing component, etc.] - Y10T 428/249995: Constituent is in liquid form - B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS - G01N: INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES (measuring or testing apparatus or processes other than immunoassay, involving enzymes or microorganisms C12M, C12Q) - Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION ## 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. ## Claims ### Claim 1 A monolith separation column for chromatography comprising: a capillary tube; a skeletal phase of an organic macromolecular gel-like monolith formed in the capillary tube; 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 2,2,2-tri-(2,3-epoxypropyl)-isocyanurate as an epoxy compound and an amine compound having two or more amino groups in a molecule, and does not contain any carbon atom constituting an aromatic compound, and wherein the monolith separation column is obtained by: (A) filling the epoxy compound, the amino compound and a porogen into a capillary tube; (B) heating the epoxy compound and the amine compound within a range of from 60 to 200° C. in the porogen to polymerize them to obtain a gel-like material in the capillary tube, and (C) then washing the gel-like material with a solvent to remove the porogen to leave the skeletal phase in the capillary tube. ### Claim 2 (depends on 1) The monolith separation column according to claim 1, wherein the separation medium has a theoretical plate number of 50000 or more theoretical plates per meter of column length. ### Claim 3 (depends on 1) The monolith separation column 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. ### Claim 4 (depends on 1) A process for producing the monolith separation medium according to claim 1, comprising the steps of: (A) a step of heating an epoxy compound and an amine compound 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, wherein the epoxy compound is 2,2,2-tri-(2, 3-epoxypropyl)-isocyanurate, wherein the amine compound has two or more amino groups in a molecule, and wherein the skeletal phase does not contain any carbon atom constituting an aromatic compound. ### Claim 5 (depends on 4) The process for producing a monolith separation medium according claim 4, wherein optically active substances are used as both the epoxy and amine compounds. ### Claim 6 (depends on 4) The process for producing a monolith separation medium according to claim 4, 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. ### Claim 7 (depends on 6) The process for producing a monolith separation medium according to claim 6, wherein the porogen is polyethylene glycol. ### Claim 8 (depends on 1) The monolith separation column according to claim 1, wherein the amine compound is bis(4-aminocyclohexyl)methane. ### Claim 9 (depends on 3) The monolith separation column according to claim 3, wherein the amine compound is (1S,2S)-(+)-1,2-cyclohexanediamine. ### Claim 10 (depends on 4) The process for producing a monolith separation medium according to claim 4, wherein the amine compound is bis(4-aminocyclohexyl)methane. ### Claim 11 (depends on 5) The process for producing a monolith separation medium according to claim 5, wherein the amine compound is (1S,2S)-(+)-1,2-cyclohexanediamine.