Liquid purification or separation – With means to add treating material – Chromatography
Reexamination Certificate
2000-02-11
2001-11-27
Therkorn, Ernest G. (Department: 1723)
Liquid purification or separation
With means to add treating material
Chromatography
C210S502100, C210S635000, C210S656000, C502S402000, C521S033000
Reexamination Certificate
active
06322695
ABSTRACT:
FIELD OF THE INVENTION
This invention relates generally to novel porous resins for solid phase extraction and chromatography which contain at least one hydrophobic component, at least one hydrophilic component and at least one ion exchange functional group.
BACKGROUND OF THE INVENTION
Solid phase extraction (SPE) is a chromatographic technique which is widely used, e.g., for preconcentration and cleanup of analytical samples, for purification of various chemicals, and for removal of toxic or valuable substances from aqueous solutions. SPE is usually performed using a column or cartridge containing an appropriate resin. SPE procedures have been developed using sorbents which can interact with analytes by hydrophobic, ion exchange, chelation, sorption, and other mechanisms, to bind and remove the analytes from fluids. Since different SPE applications can require different sorbents, there is a need for sorbents with novel properties which have unique selectivities.
SUMMARY OF THE INVENTION
It is an object of the invention to provide compounds which can be used as porous resins for solid phase extraction and chromatography which exhibit superior wetting characteristics.
It is yet another object of the invention to provide porous resin compounds which have unique selectivities.
It is yet another object of the invention to provide porous resin compounds which can selectively capture analytes of interest and allow interfering analytes to pass through unretained.
It is yet another object of the invention to provide porous resin compounds having an ion exchange functional group, a hydrophobic component and a hydrophilic polar component.
It is yet another object of the invention to utilize the novel porous resins of this invention to isolate or remove a solute from a solution.
Still another object of the invention is to utilize the novel porous resins of this invention to analytically determine the level of a solute in a solution.
In one aspect, the invention features a compound of the formula:
and salts thereof,
wherein the order of A, B and C may be random, block, or a combination of random and block;
wherein
1
100
<
(
p
+
n
)
m
<
100
1
and
1
500
<
p
n
<
100
1
wherein A is selected from the group consisting of
wherein B is selected from the group consisting of
wherein C is A or modified A, wherein modified A is selected from the group consisting of
wherein X is selected from the group consisting of SO
3
H, CH
2
CO
2
H, CH
2
CH(CO
2
H)
2
, CO
2
H, PO
3
H
2
, PO
2
H
2
, CH
2
PO
3
H
2
, CH
2
Cl, CH
2
NH
2
, CH
2
N[(CH
2
)
y
CH
3
]
2
wherein y is any integer from 0 to 18, CH
2
N
+
[(CH
2
)
y
=CH
3
]
3
D
−
wherein y= is any integer from 0 to 18 and D
−
is an anion, SO
2
NHR wherein R is polyethylenimine, and CH
2
NHR wherein R is polyethylenimine.
Another aspect of the invention is a porous resin formed by copolymerizing at least one hydrophobic monomer and at least one hydrophilic monomer so as to form a copolymer, and subjecting the copolymer to a sulfonation reaction so as to form a sulfonated copolymer comprising at least one ion-exchange functional group, at least one hydrophilic component and at least one hydrophobic component.
In preferred embodiments, the hydrophobic monomer is divinylbenzene, the hydrophilic monomer is N-vinylpyrrolidone, and the copolymer is a poly(divinylbenzene-co-N-vinylpyrrolidone). Preferably, the porous resin is a sulfonated poly(divinylbenzene-co-N-vinylpyrrolidone).
Another aspect of the invention is a porous resin for solid phase extraction or chromatography comprising at least one ion-exchange functional group, at least one hydrophilic component and at least one hydrophobic component.
Another aspect of the invention is a method for treating a solution to isolate or remove a solute. A solution having a solute is contacted with a porous resin under conditions so as to allow sorption of the solute to the porous resin. The porous resin comprises at least one ion-exchange functional group, at least one hydrophilic polar component and at least one hydrophobic component. In certain embodiments, the solute is removed from the porous resin. In certain embodiments, the ion-exchange functional group is SO
3
H, CH
2
CO
2
H, CH
2
CH(CO
2
H)
2
, CO
2
H, PO
3
H
2
, PO
2
H
2
, CH
2
PO
3
H
2
, CH
2
Cl, CH
2
NH
2
, CH
2
N[(CH
2
)
y
CH
3
]
2
wherein y is any integer from 0 to 18, CH
2
N
+
[(CH
2
)
y
=CH
3
]
3
D
−
wherein y= is any integer from 0 to 18 and D
−
is an anion, SO
2
NHR wherein R is polyethylenimine, or CH
2
NHR wherein R is polyethylenimine. In certain embodiments, the hydrophilic monomer comprises a heterocyclic group, e.g., a saturated, unsaturated or aromatic heterocyclic group. Examples include nitrogen-containing heterocyclic groups, e.g., a pyridyl group, e.g., 2-vinylpyridine, 3-vinylpyridine or 4-vinylpyridine, or a pyrrolidonyl group, e.g., N-vinylpyrrolidone. In certain embodiments, the hydrophobic monomer comprises an aromatic carbocyclic group, e.g., a phenyl group or a phenylene group, or a straight chain C
2
-C
18
-alkyl group or a branched chain C
2
-C
18
-alkyl group. The hydrophobic monomer can be, e.g., styrene or divinylbenzene. A preferred copolymer is a poly(divinylbenzene-co-N-vinylpyrrolidone). A preferred porous resin is a compound of formula I and salts thereof. Preferably, the porous resin is a sulfonated poly(divinylbenzene-co-N-vinylpyrrolidone).
Another aspect of the invention is a method for analytically determining the level of solute in a solution. A solution having a solute is contacted with a porous resin under conditions so as to allow sorption of the solute to the porous resin. The resin comprises at least one ion-exchange functional group, at least one hydrophilic polar component and at least one hydrophobic component. The porous resin having the sorbed solute is washed with a solvent under conditions so as to desorb the solute from the porous resin. The level of the desorbed solute present in the solvent after the washing is analytically determined. In certain embodiments, the porous resin is a compound of formula I and salts thereof.
Preferably, the Porous Resin is a Sulfonated poly(divinylbenzene-co-N-vinylpyrrolidone).
Another aspect of the invention is a solid phase extraction cartridge comprising a porous resin packed inside an open-ended container. The porous resin comprises at least one ion-exchange functional group, at least one hydrophilic polar component and at least one hydrophobic component. In certain embodiments, the porous resin is a compound of formula I and salts thereof. Preferably, the porous resin is a sulfonated poly(divinylbenzene-co-N-vinylpyrrolidone).
The above and other features, objects and advantages of the present invention will be better understood by a reading of the following specification in conjunction with the drawings.
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patent: 5882521 (1999-03-01), Bouvier
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Lee Peter Jeng Jong
O'Gara John E.
Janiuk Anthony J.
Therkorn Ernest G.
Waters Investments Limited
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