Separating agent for optical isomer

Abstract

Provided is a complex obtained by reacting a polymer compound derivative obtained by modifying part of 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) n R 3-n (where A, X, Y, R, and n are as defined in claim 1 ) ; (II) M(OR 1 ) n R 2 4-n ; (III) Al(OR 1 ) p R 2 3-p ; (IV) Mg(OR 1 ) g R 2 2-q (where M, R 1 , R 2 , n, p, and q are as defined in claim 1 ); and (V) (where R 3 , R 4 , R 5 , and R 6 are as defined in claim 1 ).

1 . A complex obtained by causing a polymer compound derivative obtained by modifying part of hydroxy or amino groups of a polymer compound having the hydroxy or amino groups with a compound represented by the following general formula (I) and one or more kinds of compounds represented by the following general formulae (II) to (V) to react with each other:
   [Chem 1]     A-X—Si(Y) n R 3-n    (I)   where A represents a reactive group that 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 that 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;
   [Chem 2] 
   M(OR 1 ) p R 2   4-n    (II) 
   [Chem 3] 
   Al(OR 1 ) p R 2   3-p    (III) 
   [Chem 4] 
   Mg(OR 1 ) q R 2   2-q    (IV) 
   where M represents silicon (Si), titanium (Ti), zirconium (Zr), or chromium (Cr), 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, n represents an integer of 1 to 4, p represents an integer of 1 to 3, and q represents an integer of 1 or 2;
   [Chem 5] 
   [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 complex according to  claim 1 , wherein the polymer compound is an optically active organic polymer compound. 
     
     
         3 . The complex according to  claim 2 , wherein the optically active organic polymer compound is a polysaccharide. 
     
     
         4 . The complex according to  claim 3 , wherein the polysaccharide is cellulose or amylose. 
     
     
         5 . The complex according to  claim 1 , wherein the compound represented by the general formula (1) is 3-isocyanatepropyltriethoxysilane, 3-isocyanatepropyltrimethoxysilane, 3-isocyanatepropyldiethoxymethylsilane, 2-isocyanateethyltriethoxysilane, 4-isocyanatephenyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, or 3-thiocyanatepropyltriethoxysilane. 
     
     
         6 . The complex according to  claim 1 , wherein a ratio of introduction of the molecules of the compound represented by the general formula (I) into the hydroxy or amino groups of the polymer compound having the hydroxy or amino groups is 1.0 to 35%. 
     
     
         7 . The complex according to  claim 1 , wherein at least part of the hydroxy or amino groups except the hydroxy or amino groups 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 which acts on an optical isomer. 
     
     
         8 . The complex according to  claim 7 , wherein the molecules of the compound having a functional group which acts on an optical isomer are introduced into the at least part of the hydroxy or amino groups except the hydroxy or amino groups 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. 
     
     
         9 . The complex according to  claim 7 , wherein the compound having a functional group which acts on an optical isomer comprises a compound containing an atomic group represented by the following general formula (VI) or (VII):
   [Chem 6]     —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.   
     
     
         10 . The complex according to  claim 9 , wherein the compound having a functional group which acts on an optical isomer is 3,5-dimethylphenyl isocyanate. 
     
     
         11 . The complex according to  claim 1 , wherein a content of the polymer compound derivative is 10 to 90 wt % with respect to a total amount of the complex. 
     
     
         12 . The complex according to  claim 1 , wherein the compounds represented by the general formula (II) comprise one or more compounds selected from the group consisting of tetraethoxysilane, tetramethoxysilane, tetra-n-propoxysilane, tetraisopropoxysilane, tetra-n-butoxysilane, tetraisobutoxysilane, tetra-sec-butoxysilane, tetra-t-butoxysilane, tetrapentyloxysilane, tetrahexyloxysilane, triethoxymethylsilane, and triethoxyphenylsilane. 
     
     
         13 . The complex 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. 
     
     
         14 . The complex according to  claim 1 , wherein the complex is in a bead form. 
     
     
         15 . A method of producing a complex, the method comprising the steps of:
 dissolving a polymer compound derivative obtained by modifying part of hydroxy or amino groups of a polymer compound having the hydroxy or amino groups with a compound represented by the following general formula (I) and one or more kinds of compounds represented by the following general formulae (II) to (V) in an organic solvent to prepare a solution; and   dropping the solution into an aqueous solution of a surfactant or a proton-donating solvent while stirring the aqueous solution or the solvent:
   [Chem 7] 
   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.
   [Chem 8] 
   M(OR 1 ) n R 2   4-n    (II) 
   [Chem 9] 
   Al(OR 1 ) p R 2   3-p    (III) 
   [Chem 10] 
   Mg(OR 1 ) q R 2   2-q    (IV) 
   where M represents silicon (Si), titanium (Ti), zirconium (Zr), or chromium (Cr), 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, n represents an integer of 1 to 4, p represents an integer of 1 to 3, and q represents an integer of 1 or 2;
   [Chem 11] 
   [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.   
     
     
         16 . A separating agent for optical isomers, the separating agent comprising the complex according to  claim 1 .