Polymer for filler for preprocessing column
View Patent ↗The present invention provides a polymer of the compound represented by formula [1]: and the compound represented by formula [2]: to a glycidyl group of which an anion exchanging group is introduced; a filler for measuring an acidic group binding to a perfluoro compound at a terminal, which comprises the polymer; a column filled with the filler; a method for measuring said perfluoro compound having an acidic group at a terminal by using the column; a filler or a column filled with the filler comprising the polymer for measuring a drug; and a method for measuring a drug by using the column.
1. A method of measuring a perfluoro compound having an acidic group at a terminal, comprising steps of:
contacting the perfluoro compound with a polymer,
wherein the polymer includes a prepolymer having an anion exchange group attached to a gycidyl group of the prepolymer,
the prepolymer is a polymerization product of a compound of formula [1]:
wherein each of R 1 and R 2 independently represents a hydrogen atom, a linear alkyl group having from 1 to 3 carbon atoms or a halogen atom, and Bz represents benzene ring, and
a compound of formula [2]:
wherein R 9 represents a hydrogen atom, a linear alkyl group having from 1 to 3 carbon atoms or a halogen atom, R 10 represents a linear alkylene group having from 1 to 3 carbon atoms, and each of R 11 and R 12 independently represents a hydrogen atom or a linear alkyl group having from 1 to 6 carbon atoms, and
a molar ratio of the compound of the formula [1]/ the compound of the formula [2]is in a range from 60/40 to 90/10; and
measuring the perfluoro compound.
2. The method of claim 1 , further comprising eluting at least a portion of the perfluoro compound with an eluting solution having a pH in arrange from 8 to 14.
3. The method of claim 2 , further comprising subjecting an eluted portion of the perfluoro compound to mass spectrometry.
4. The method of claim 2 , further comprising, prior to the eluting step, contacting at least a portion the perfluoro compound with a washing solution having a pH of 8 or less.
5. The method of claim 1 , wherein the prepolymer is formed by mixing the compound of the formula [1]with the compound of the formula [2]in a non-aqueous, organic solution so as to form an organic mixture.
6. The method of claim 5 , further comprising thereafter adding the organic mixture to an aqueous solution so as to form a suspension polymerization mixture.
7. The method of claim 6 , further comprising subjecting the suspension polymerization mixture to an elevated temperature in a range from 60 to 90 degrees Celsius.
8. The method of claim 7 , wherein the suspension polymerization mixture is subjected to the elevated temperature for a period in a range from 4 to 20 hours.
9. The method of claim 1 , wherein the polymer is formed by attaching to the prepolymer at least one amino group selected from the group consisting of a secondary amino group, a tertiary amino group and a quaternary amino group as the anion exchanging group.
10. The method of claim 1 , wherein the polymer is formed by attaching to the prepolymer a tertiary amino group as the anion exchanging group.
11. The method of claim 1 , wherein the polymer is formed by attaching to the prepolymer a morpholino group or a diethylamino group as the anion exchanging group.
12. The method of claim 1 , wherein the perfluoro compound is has as the acidic group at the terminal, a sulfo group, a carboxyl group, or a hydroxyl group.
13. The method of claim 1 , wherein the polymer has an average particle size in a range from 10 to 100 microns.
14. The method of claim 1 , wherein the polymer is used as a filler in a preprocessing column that measures the perfluoro compound.
15. The method of claim 1 , wherein the anion exchanging group has an ammonium group represented by formula [3]:
wherein each of R 3 represents independently a linear alkyl group having from 1 to 3 carbon atoms, and R 4 represents a linear alkyl group having from 1 to 6 carbon atoms.
16. A method of measuring drugs, comprising steps of:
contacting at least one drug with a polymer,
wherein the polymer includes a prepolymer having an anion exchange group attached to a gycidyl group of the prepolymer,
the prepolymer is a polymerization product of a compound of formula [1]:
wherein each of R 1 and R 2 independently represents a hydrogen atom, a linear alkyl group having from 1 to 3 carbon atoms or a halogen atom, and Bz represents benzene ring,
a compound of formula [2]:
wherein R 9 represents a hydrogen atom, a linear alkyl group having from 1 to 3 carbon atoms or a halogen atom, R 10 represents a linear alkylene group having from 1 to 3 carbon atoms, and each of R 11 and R 12 independently represents a hydrogen atom or a linear alkyl group having from 1 to 6 carbon atoms, and further
a compound of formula [4]:
wherein each of three R 15 represents independently a linear alkylene group having from 1 to 3 carbon atoms, each of three R 16 independently represents a hydrogen atom, and a linear alkyl group having from 1 to 3 carbon atoms or a halogen atom, and
the anion exchanging group has an ammonium group represented by formula [3]:
wherein each of R 3 represents independently a linear alkyl group having from 1 to 3 carbon atoms, and R 4 represents a linear alkyl group having from 1 to 6 carbon atoms; and
measuring the at least one drug.
17. The method of claim 16 ,
wherein a molar ratio of the compound of the formula [1], the compound of the formula [2], and the compound of the formula [4]is in ranges from 60 to 85 : from 14 to 30: from 1 to 10, respectively.
18. A method of measuring a perfluoro compound having an acidic group at terminal, comprising steps of:
contacting the perfluoro compound with a polymer,
wherein the polymer consists of a prepolymer having an anion exchange group attached to a gycidyl group of the prepolymer,
the prepolymer is a polymerization product of a compound of formula [1]:
wherein each of R 1 and R 2 independently represents a hydrogen atom, a linear alkyl group having from 1 to 3 carbon atoms, or a halogen atom, and Bz represents benzene ring, and
a compound of formula [2]:
wherein R 9 represents a hydrogen atom, a linear alkyl group having from 1 to 3 carbon atoms or a halogen atom, R 10 represents a linear alkylene group having from 1 to 3 carbon atoms, and each of R 11 and R 12 independently represents a hydrogen atom or a linear alkyl group having from 1 to 6 carbon atoms, and
a molar ratio of the compound of the formula [1]/ the compound of the formula [2]is in a range from 60/40 to 90/10 ;
contacting at least a portion the perfluoro compound with a washing solution having a pH of 8 or less;
eluting at least a portion of the perfluoro compound with an eluting solution having a pH in a range from 8 to 14;
subjecting an eluted portion of the perfluoro compound to mass spectrometry; and
measuring the perfluoro compound.
19. The method of claim 18 , wherein the prepolymer is formed by steps comprising:
a) mixing the compound of the formula [1]with the compound of the formula [2]in a non-aqueous, organic solution so as to form an organic mixture;
b) adding the organic mixture to an aqueous solution so as to form a suspension polymerization mixture; and
c) subjecting the suspension polymerization mixture to an elevated temperature in a range from 60 to 90 degrees Celsius for a period in a range from 4 to 20 hours.