Separating agent for optical isomer

Patent metadata

Field	Value
Publication number	US-10836834-B2
Application number	US-201615217519-A
Country	US
Kind code	B2
Filing date	Jul 22, 2016
Priority date	May 7, 2007
Publication date	Nov 17, 2020
Grant date	Nov 17, 2020

Abstract

Provided is a complex obtained by reacting a polymer compound derivative obtained by modifying part of the hydroxy groups or amino groups of a polymer compound having the hydroxy groups or amino groups with a compound represented by the following general formula (I) with one or more kinds of compounds represented by the following general formulae (II) to (V): (I) A-X—Si(Y)nR3-n; (II) M(OR1)nR24-n; (III) Al(OR1)pR23-p; (IV) Mg(OR1)qR22-q; and (V) [Si(OR3)nR43-n]—(X)—[Si(OR5)nR63-n].

First claim

What is claimed is:

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.

Assignees

• Daicel Corp

Inventors

• Okamoto Yoshio
• Yamamoto Chiyo
• Ikai Tomoyuki
• Kamigaito Masami

Classifications

• C08B3/14 Primary

  in which the organic acid residue contains substituents, e.g. NH2, Cl · CPC title

• C08B33/02

  Esters · CPC title

• G01N30/88

  Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86 · CPC title

• C08B15/05

  Derivatives containing elements other than carbon, hydrogen, oxygen, halogens or sulfur (esters or phosphorous acids C08B5/00) · CPC title

• B01J20/265 Primary

  modified or post-treated polymers (polymer carriers or substrates subjected to further impregnating or coating B01J20/3208) · CPC title