Porous polymeric resins
Assignee3M Innovative Properties Company
InventorsPeter D. Wickert, Simon K. Shannon, Kannan Seshadri, Jerald K. Rasmussen, James I. Hembre, Robert T. Fitzsimons, Jr.
Life of this patent
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Abstract
Porous polymeric resins, reaction mixtures and methods that can be used to prepare the porous polymeric resins, and uses of the porous polymeric resin are described. More specifically, the polymeric resins typically have a hierarchical porous structure plus reactive groups that can be used to interact with or react with a variety of different target compounds. The reactive groups can be selected from an acidic group or a salt thereof, an amino group or salt thereof, a hydroxyl group, an azlactone group, a glycidyl group, or a combination thereof.
Claims18
A reaction mixture comprising:
- an aqueous phase composition comprising
- a) a monomer mixture comprising
- 1) a crosslinking monomer of Formula (I)
- wherein
- R1 is hydrogen or methyl;
- Q is oxy or —NH—;
- and
- Y is an alkylene or heteroalkylene, wherein the alkylene or heteroalkylene is unsubstituted or substituted with a hydroxyl group;
- and
- 2) a functional monomer having (a) an ethylenically unsaturated group and (b) a functional group selected from (1) an acidic group or a salt thereof, (2) an amino group or a salt thereof, (3) a hydroxyl group, (4) an azlactone group, (5) a glycidyl group, or (6) a combination thereof;
- b) dispersed organic aggregates in the size range of 0.05 to 5 micrometers, wherein the organic aggregate comprises
- 1) a compound having a hydrocarbon hydrophobic group and a poly(alkylene oxide) hydrophilic group;
- or
- 2) a wax stabilized with a surfactant;
- or
- 3) a hydrophobic polymer stabilized with a surfactant;
- and
- c) an aqueous phase solvent comprising water and an optional polar organic solvent that is miscible with water;
- wherein the organic aggregates are not soluble in the aqueous phase solvent and wherein the aqueous phase composition contains 0.5 to 10 weight percent dispersed organic aggregates based on the total weight of the aqueous phase composition.
A method of preparing a porous polymeric resin, the method comprising:
- forming an aqueous phase composition comprising:
- a) a monomer mixture comprising
- 1) a crosslinking monomer of Formula (I)
- wherein
- R1 is hydrogen or methyl;
- Q is oxy or —NH—;
- and
- Y is an alkylene or heteroalkylene, wherein the alkylene or heteroalkylene is unsubstituted or substituted with a hydroxyl group;
- and
- 2) a functional monomer having (a) an ethylenically unsaturated group and (b) a functional group selected from (1) an acidic group or a salt thereof, (2) an amino group or a salt thereof, (3) a hydroxyl group, (4) an azlactone group, (5) a glycidyl group, or (6) a combination thereof;
- b) dispersed organic aggregates in the size range of 0.05 to 5 micrometers, wherein the organic aggregate comprises
- 1) a compound having a hydrocarbon hydrophobic group and a poly(alkylene oxide) hydrophilic group;
- or
- 2) a wax stabilized with a surfactant;
- or
- 3) a hydrophobic polymer stabilized with a surfactant;
- and
- c) an aqueous phase solvent comprising water and an optional polar organic solvent that is miscible with water;
- wherein the organic aggregates are not soluble in the aqueous phase solvent and wherein the aqueous phase composition contains 0.5 to 10 weight percent organic dispersed aggregates based on the total weight of the aqueous phase composition;
- polymerizing the monomer mixture to form polymeric material that contains the organic aggregates;
- and
- removing at least a portion of the organic aggregates from the polymeric material to form the porous polymeric resin.
A method for purifying or separating a target compound, the method comprising:
- forming a porous polymeric resin, the forming comprising:
- preparing an aqueous phase composition comprising
- a) a monomer mixture comprising
- 1) a crosslinking monomer of Formula (I)
- wherein
- R1 is hydrogen or methyl;
- Q is oxy or —NH—;
- and
- Y is an alkylene or heteroalkylene, wherein the alkylene or heteroalkylene is unsubstituted or substituted with a hydroxyl group;
- and
- 2) a functional monomer having (a) an ethylenically unsaturated group and (b) a functional group selected from (1) an acidic group or a salt thereof, (2) an amino group or a salt thereof, (3) a hydroxyl group, (4) an azlactone group, (5) a glycidyl group, or (6) a combination thereof;
- b) dispersed organic aggregates in the size range of 0.05 to 5 micrometers, wherein the organic aggregate comprises
- 1) a compound having a hydrocarbon hydrophobic group and a poly(alkylene oxide) hydrophilic group;
- or
- 2) a wax stabilized with a surfactant;
- or
- 3) a hydrophobic polymer stabilized with a surfactant;
- and
- c) an aqueous phase solvent comprising water and an optional polar organic solvent that is miscible with water;
- wherein the organic aggregates are not soluble in the aqueous phase solvent and wherein the aqueous phase composition contains 0.5 to 10 weight percent dispersed organic aggregates based on the total weight of the aqueous phase composition;
- polymerizing the monomer mixture to form polymeric material that contains the organic aggregates;
- and
- removing at least a portion of the organic aggregates from the polymeric material to form the porous polymeric resin;
- and
- contacting the porous polymeric resin with a sample containing a target compound, wherein the target compound interacts with or reacts with at least one functional group of the porous polymeric resin.
A method for purifying or separating a target compound, the method comprising:
- forming a porous polymeric resin, the forming comprising:
- preparing an aqueous phase composition comprising
- a) a monomer mixture comprising
- 1) a crosslinking monomer of Formula (I)
- wherein
- R1 is hydrogen or methyl;
- Q is oxy or —NH—;
- and
- Y is an alkylene or heteroalkylene, wherein Y can be optionally substituted with a hydroxyl group;
- and
- 2) a functional monomer having (a) an ethylenically unsaturated group and (b) a first functional group selected from (1) an acidic group or a salt thereof, (2) an amino group or a salt thereof, (3) a hydroxyl group, (4) an azlactone group, (5) a glycidyl group, or (6) a combination thereof;
- b) dispersed or suspended organic aggregates in the size range of 0.05 to 5 micrometers, wherein the organic aggregate comprises
- 1) a compound having a hydrocarbon hydrophobic group and a poly(alkylene oxide) hydrophilic group;
- or
- 2) a wax stabilized with a surfactant;
- or
- 3) a hydrophobic polymer stabilized with a surfactant;
- and
- c) an aqueous phase solvent comprising water and an optional polar organic solvent that is miscible with water;
- wherein the organic aggregates are not soluble in the aqueous phase solvent and wherein the aqueous phase composition contains 0.5 to 10 weight percent dispersed organic aggregates based on the total weight of the aqueous phase composition;
- suspending the aqueous phase composition in organic phase that is not miscible with water, the organic phase comprising a non-polar organic solvent;
- polymerizing the monomer mixture to form polymeric material that contain the organic aggregates;
- and
- removing at least a portion of the organic aggregates from the polymeric material to form the porous polymeric resin;
- preparing modified porous polymeric resin comprising treating the porous polymeric resin with a modifying agent and converting the first functional group to a second functional group;
- and
- contacting the modified porous polymeric resin with a sample containing a target compound, wherein the target compound interacts with or reacts with the second functional group of the modified porous polymeric resin.
Dependencies are inferred from the claim text.