Separating agent for optical isomer

1. A method of producing a complex, the method comprising the steps of:

dissolving the following (A) and (B) in an organic solvent to prepare a solution,

wherein (A) is a polysaccharide derivative obtained by modifying part of hydroxy or amino groups of a polysaccharide having a number average degree of polymerization of at least 5 with a compound represented by the following general formula (I),

wherein (B) is one or more kinds of compounds selected from tetraethoxysilane, tetramethoxysilane, tetra-n-propoxysilane, tetraisopropoxysilane, tetra-n-butoxysilane, tetraisobutoxysilane, tetra-sec-butoxysilane, tetra-t-butoxysilane, tetrapentyloxysilane, tetrahexyloxysilane, triethoxymethylsilane, triethoxyphenylsilane, compounds represented by the following general formula (III), compounds represented by the following general formula (IV), and compounds represented by the following general formula (V); and

dropping the solution into an aqueous solution of a surfactant or a proton-donating solvent while stirring the aqueous solution or the solvent:

A-X—Si(Y) n R 3-n   (I)

where A represents a reactive group which reacts with a hydroxy or amino group, X represents an alkylene group which has 1 to 18 carbon atoms and which may have a branch, or an arylene group which may have a substituent, Y represents a reactive group which reacts with a silanol group to form a siloxane bond, R represents an alkyl group which has 1 to 18 carbon atoms and which may have a branch, or an aryl group which may have a substituent, and n represents an integer of 1 to 3;

Al(OR 1 ) p R 2 3-p   (III)

Mg(OR 1 ) q R 2 2-q   (IV)

where Al represents aluminum, Mg represents magnesium, R 1 represents hydrogen or an alkyl group having 1 to 12 carbon atoms, R 2 represents an alkyl group which has 1 to 18 carbon atoms and which may have a branch or an aryl group which may have a substituent, p represents an integer of 1 to 3, and q represents an integer of 1 or 2;

[Si(OR 3 ) n R 4 3-n ]—(X)—[Si(OR 5 ) n R 6 3-n]   (V)

where R 3 , R 4 , R 5 , and R 6 each independently represent an alkyl group which has 1 to 18 carbon atoms and which may have a branch or an aryl group which may have a substituent, and X represents an alkylene group which has 1 to 18 carbon atoms and which may have a branch or an arylene group which may have a substituent.

2. The method according to claim 1 , wherein the polysaccharide is cellulose or amylose.

3. The method according to claim 1 , wherein the compound represented by the general formula (I) is

3-isocyanatepropyltriethoxysilane,

3-isocyanatepropyltrimethoxysilane,

3-isocyanatepropyldiethoxymethylsilane,

2-isocyanateethyltriethoxysilane,

4-isocyanatephenyltriethoxysilane,

3-glycidoxypropyltrimethoxysilane,

3-glycidoxypropyltriethoxysilane, or

3-thiocyanatepropyltriethoxysilane.

4. The method according to claim 1 , wherein a numerical value obtained by multiplying a ratio of the sum of the numbers of hydroxy groups and amino groups modified with the molecules of the compound represented by the general formula (I) to the sum of the total number of the hydroxy and the total number of the amino groups by 100% is 1.0 to 35%.

5. The method according to claim 1 , wherein at least part of the hydroxy or amino groups of the polysaccharide, except the hydroxy or amino groups of the polysaccharide modified with the molecules of the compound represented by the general formula (I), are further modified with molecules of a compound having a functional group selected from a group containing an aromatic group, which optionally may have a substituent, and an aliphatic group having a cyclic structure.

6. The method according to claim 5 , wherein the molecules of the compound having a functional group are introduced into the at least part of the hydroxy or amino groups of the polysaccharide, except the hydroxy or amino groups of the polysaccharide modified with the molecules of the compound represented by the general formula (I), through a urethane bond, a urea bond, an ester bond, or an ether bond.

7. The method according to claim 5 , wherein the compound having a functional group comprises a compound containing an atomic group represented by the following general formula (VI) or (VII):

—CO—R′  (VI)

—CO—NH—R′  (VII)

where 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, a cyano group, a halogen, a hydroxy group, a nitro group, an amino group, and a dialkylamino group containing two alkyl groups each having 1 to 8 carbon atoms.

8. The method according to claim 7 , wherein the compound having a functional group is 3,5-dimethylphenyl isocyanate.

9. The method according to claim 1 , wherein a content of the polysaccharide derivative is 10 to 90 wt % with respect to a total amount of the complex.

10. The method according to claim 1 , wherein the compounds represented by the general formula (V) comprise one or more compounds selected from the group consisting of bis(trimethoxysilyl)methane, bis(triethoxysilyl)methane, 1,1-bis(trimethoxysilyl)ethane, 1,1-bis(triethoxysilyl)ethane, 1,2-bis(trimethoxysilyl)ethane, 1,3-bis(trimethoxysilyl)propane, 1,3-bis(triethoxysilyl)propane, 2,2-bis(trimethoxysilyl)propane, 2,2-bis(triethoxysilyl)propane, 1,4-bis(trimethoxysilyl)benzene, 1,4-bis(triethoxysilyl)benzene, and 1,2-bistriethoxysilylethane.

11. The method according to claim 1 , wherein the complex is in a bead form.