Separating agent for optical isomer

• US 20120007011A1
• Filed: 04/28/2010
• Published: 01/12/2012
• Est. Priority Date: 04/30/2009
• Status: Active Grant

• Current Assignee: Daicel Chemical Industries Limited (Daicel Corporation), Nagoya University
• Original Assignee: Daicel Chemical Industries Limited (Daicel Corporation), Nagoya University
• Inventors: Yashima, Eiji, Tamura, Kazumi
• Granted Patent: US 9,028,684 B2
• Time in Patent Office: Days
• US Class Current: 252/60
• CPC Class Codes: B01J 20/29 Chiral phases
• CPC Class Codes: B01J 20/3204 Inorganic carriers, supports or substrates
• CPC Class Codes: B01J 20/321 consisting of a polymer obtained by reactions involving only carbon to carbon unsaturated bonds
• CPC Class Codes: B01J 20/3219 involving a particular spacer or linking group, e.g. for attaching an active group
• CPC Class Codes: B01J 20/3274 Proteins, nucleic acids, polysaccharides, antibodies or antigens
• CPC Class Codes: B01J 20/328 Polymers on the carrier being further modified

Abstract

Disclosed is a separating agent for optical isomer which is excellent in optical separation ability. Specifically disclosed is a separating agent for optical isomer comprising: an inclusion complex including a π-conjugated polymer in a polymer compound having a hydroxy group or an amino group; and a carrier, the inclusion complex being carried by the carrier.

Claims

1. A separating agent for optical isomers, comprising:

an inclusion complex including a π

-conjugated polymer in a polymer compound having a hydroxy group or an amino group; and

a carrier, the inclusion complex being carried by the carrier.

2. A separating agent for optical isomers according to claim 1, wherein the polymer compound is an optically active organic polymer compound.

3. A separating agent for optical isomers according to claim 2, wherein the optically active organic polymer compound is a polysaccharide.

4. A separating agent for optical isomers according to claim 3, wherein the polysaccharide is amylose or cellulose.

5. A separating agent for optical isomers according to claim 1, wherein the π

-conjugated polymer is polyphenylenevinylene, polyphenyleneethynylene, polyphenylene, polythiophene, polypyrrole, or polyacetylene.

6. A separating agent for optical isomers according to claim 5, wherein the polymer compound is amylose and the π

-conjugated polymer is polyphenylenevinylene.

7. A separating agent for optical isomers according to claim 6, wherein the inclusion complex is obtained by polymerizing, in a solution in which amylose is dissolved, a monomer that produces a constitutional unit represented by the following formula (I) after the polymerization.

8. A separating agent for optical isomers according to claim 7, wherein the monomer that produces the unit represented by the formula (I) after the polymerization is p-xylylenebis(tetrahydrothiophenium)dichloride.

9. A separating agent for optical isomers according to claim 1, wherein at least part of the hydroxy group or amino group of the polymer compound is modified with a compound having a functional group which acts on an optical isomer.

10. A separating agent for optical isomers according to claim 9, wherein the compound having a functional group which acts on an optical isomer is introduced through a urethane bond, a urea bond, an ester bond, or an ether bond.

11. A separating agent for optical isomers according to claim 10, wherein the compound having a functional group which acts on an optical isomer is a compound that produces an atomic group represented by the following general formula (II) or (III) when introduced into the at least part of the hydroxy group or amino group of the polymer compound:

—

CO—

R′

 

 

(II)

—

CO—

NH—

R′

 

 

(III)

in the formulae (II) and (III), R′

represents an aliphatic or aromatic hydrocarbon group which may contain a heteroatom, and the aliphatic or aromatic hydrocarbon group may be unsubstituted or may be substituted with one or more groups selected from the group consisting of a hydrocarbon group which has 1 to 12 carbon atoms and which may contain a heteroatom, an alkoxy group which has 1 to 12 carbon atoms and which may contain a heteroatom, a cyano group, a halogen group, a hydroxy group, a nitro group, an amino group, and a dialkylamino group containing two alkyl groups each having 1 to 8 carbon atoms.

12. A separating agent for optical isomers according to claim 11, wherein the compound having a functional group which acts on an optical isomer is 3,5-dimethylphenyl isocyanate.