Charge-bearing cyclodextrin polymeric materials and methods of making and using same
AssigneeCycloPure, Inc.
InventorsGokhan Barin, Jason M. Spruell, Moira Brown, Shan Li
Life of this patent
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Abstract
The present disclosure relates to charge-bearing polymeric materials and methods of their use for purifying fluid samples from micropollutants, such as anionic micropollutants.
Claims30
A porous polymeric material comprising a plurality of cyclodextrins crosslinked with a plurality of polyisocyanate crosslinkers, wherein one or more of the plurality of cyclodextrins are bound to a linker of formula (I):
- wherein
- A is an aryl or heteroaryl moiety;
- each R1 is independently selected from the group consisting of H, C1-C6 alkyl, C1-C3 haloalkyl, aryl, heteroaryl, —CF3, —SO3H, —CN, —NO2, —NH2, —NCO, —C(O)2R3, —C(O)N(R3)2, and -halogen;
- each R2 is independently H, —OH, —O-metal cation, alkyl, aryl, heteroaryl, —SH, —S-metal cation, —S-alkyl, —C(O)2H, or —C(O)NH2;
- each R3 is independently —H, —C1-C6 alkyl, —C1-C3 haloalkyl, -aryl, —C(O)N(Ra)(Rb), —C(O)Rc, —CO2Rc, —SO2N(Ra)(Rb), or —SORc, wherein each Ra, Rb, and Rc is independently H, or C1-C6 alkyl;
- each W is independently a bond, an alkylene group, an arylene group, a heteroarylene group, —O-arylene-, —(CH2)a-arylene-, —SO2-arylene-, —NH-arylene-, —S-arylene-, —O— heteroarylene-, —(CH2)a-heteroarylene-, —SO2-heteraoarylene-, —NH-heteroarylene-, —S— heteroarylene-, —(—O—(CH2)a—)x—, —(—NH—(CH2)a—)x—, —(—S—(CH2)a—)x—,
- wherein a is 0-100 and x is 1-100, and each arylene or heteroarylene moiety can be substituted or unsubstituted;
- each Z is an anionic moiety;
- each L is
- A′ is a covalent bond to A;
- Z′ is a covalent bond to Z;
- * is a covalent bond to ;
- is a point of attachment to the plurality of cyclodextrin carbon atoms;
- x is 0-8;
- y1 is 1-4;
- y2 is 1-4;
- and
- y3 is 0-4.
A porous polymeric material comprising a plurality of cyclodextrins crosslinked with a plurality of acid chloride-containing crosslinkers or ester-containing crosslinkers, wherein one or more of the plurality of cyclodextrins are bound to a linker of formula (I):
- wherein
- A is an aryl or heteroaryl moiety;
- each R1 is independently selected from the group consisting of H, C1-C6 alkyl, C1-C3 haloalkyl, aryl, heteroaryl, —CF3, —SO3H, —CN, —NO2, —NH2, —NCO, —C(O)2R3, —C(O)N(R3)2, and -halogen;
- each R2 is independently H, —OH, —O-metal cation, alkyl, aryl, heteroaryl, —SH, —S-metal cation, —S-alkyl, —C(O)2H, or —C(O)NH2;
- each R3 is independently —H, —C1-C6 alkyl, —C1-C3 haloalkyl, -aryl, —C(O)N(Ra)(Rb), —C(O)Rc, —CO2Rc, —SO2N(Ra)(Rb), or —SORc, wherein each Ra, Rb, and Rc is independently H, or C1-C6 alkyl;
- each W is independently a bond, an alkylene group, an arylene group, a heteroarylene group, —O-arylene-, —(CH2)a-arylene-, —SO2-arylene-, —NH-arylene-, —S-arylene-, —O— heteroarylene-, —(CH2)a-heteroarylene-, —SO2-heteraoarylene-, —NH-heteroarylene-, —S— heteroarylene-, —(—O—(CH2)a—)x—, —(—NH—(CH2)a—)x—, —(—S—(CH2)a—)x—,
- wherein a is 0-100 and x is 1-100, and each arylene or heteroarylene moiety can be substituted or unsubstituted;
- each Z is a cationic or anionic moiety;
- each L is
- A′ is a covalent bond to A;
- Z′ is a covalent bond to Z;
- * is a covalent bond to ;
- is a point of attachment to the plurality of cyclodextrin carbon atoms;
- x is 0-8;
- y1 is 1-4;
- y2 is 1-4;
- and
- y3 is 0-4.
Dependencies are inferred from the claim text.