NZ794050B2 - Charge-bearing cyclodextrin polymeric materials and methods of making and using same - Google Patents
Charge-bearing cyclodextrin polymeric materials and methods of making and using sameInfo
- Publication number
- NZ794050B2 NZ794050B2 NZ794050A NZ79405020A NZ794050B2 NZ 794050 B2 NZ794050 B2 NZ 794050B2 NZ 794050 A NZ794050 A NZ 794050A NZ 79405020 A NZ79405020 A NZ 79405020A NZ 794050 B2 NZ794050 B2 NZ 794050B2
- Authority
- NZ
- New Zealand
- Prior art keywords
- polymeric material
- porous polymeric
- cyclodextrin
- moiety
- fluid sample
- Prior art date
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Abstract
The present disclosure relates to charge-bearing polymeric materials and methods of their use for purifying fluid samples from micropollulants, such as anionic micropollutants.
Claims (30)
1. 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, al 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), or Ra)(Rb), wherein each Ra and Rb is independently H, or C1-C6 alkyl; each W is independently a bond, an alkylene group, an arylene group, a heteroarylene group, -O-arylene-, a-arylene-, -SO2-arylene-, -NH-arylene-, lene-, -O- heteroarylene-, -(CH2)a-heteroarylene-, -SO2-heteroarylene-, -NH-heteroarylene-, -S- heteroarylene-, –(–O–(CH2)a–)x–, (CH2)a–)x–, –(–S–(CH2)a–)x–, , or , 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 nt 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.
2. The porous polymeric material of claim 1, wherein each Z is , , , , , , or .
3. The porous polymeric material of claim 1, wherein each cyclodextrin is selected from the group consisting of a-cyclodextrin, ß-cyclodextrin, ?-cyclodextrin, and ations thereof.
4. The porous polymeric al of claim 1, wherein x and y3 are each 0.
5. The porous polymeric material of claim 1, wherein the aryl moiety is , , , , , , , , , , , , , , , , , , , or , wherein represents any of the substituents attached to A in formula (I).
6. The porous ric material of claim 5, wherein the polyisocyanate crosslinker is 4,4’- methylene diphenyl diisocyanate, the aryl moiety is and x and y3 are each 0.
7. The porous polymeric material of claim 6, wherein each cyclodextrin is a ß-cyclodextrin.
8. The porous ric material of claim 5, wherein the polyisocyanate crosslinker is toluene 2,4-diisocyanate, the aryl moiety is and x and y3 are each 0.
9. The porous polymeric material of claim 8, wherein each cyclodextrin is a ß-cyclodextrin.
10. The porous polymeric material of claim 1, wherein the polymer has a surface area from about 10 m2/g to about 2,000 m2/g.
11. A porous ric material comprising a plurality of cyclodextrins crosslinked with a ity 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): 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, (Ra)(Rb), or Ra)(Rb), wherein each Ra and Rb is independently H, or C1-C6 alkyl; each W is independently a bond, an alkylene group, an arylene group, a arylene group, -O-arylene-, -(CH2)a-arylene-, -SO2-arylene-, -NH-arylene-, -S-arylene-, -O- heteroarylene-, -(CH2)a-heteroarylene-, -SO2-heteroarylene-, -NH-heteroarylene-, -S- heteroarylene-, –(–O–(CH2)a–)x–, –(–NH–(CH2)a–)x–, –(–S–(CH2)a–)x–, , or , 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 or ; 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.
12. The porous ric al of claim 11, wherein each Z is an anionic moiety and the c moiety is , , , , , , or .
13. The porous polymeric material of claim 11, wherein each Z is a ic moiety and the cationic moiety is –N(R3)3+, –P(R3)3+, –S(R3)2+, or -Heteroaryl+.
14. The porous polymeric material of claim 13, wherein each cationic moiety is –N(R3)3+.
15. The porous polymeric material of claim 13, wherein each cationic moiety is –N(Me)3+.
16. The porous ric material of claim 11, wherein each cyclodextrin is selected from the group consisting of a-cyclodextrin, ß-cyclodextrin, ?-cyclodextrin, and combinations thereof.
17. The porous polymeric al of claim 11, wherein x and y3 are each 0.
18. The porous polymeric material of claim 11, wherein the aryl moiety is , , , , , or , wherein represents any of the substituents attached to A in a (I).
19. The porous polymeric material of claim 18, wherein the aryl moiety is or , and x and y3 are each 0.
20. The porous polymeric material of claim 19, wherein each cyclodextrin is a ß- cyclodextrin.
21. The porous polymeric material of claim 18, wherein the aryl moiety is and x and y3 are each 0.
22. The porous polymeric material of claim 21, wherein each cyclodextrin is a ßcyclodextrin.
23. The porous polymeric material of claim 18, wherein the aryl moiety is and x and y3 are each 0.
24. The porous ric al of claim 23, wherein each cyclodextrin is a ß- cyclodextrin.
25. The porous polymeric material of claim 11, wherein the polymer has a surface area from about 10 m2/g to about 2,000 m2/g.
26. A method of purifying a fluid sample comprising one or more pollutants, the method comprising contacting the fluid sample with the porous polymeric material of claim 1, whereby at least 50 wt. % of the total amount of the one or more pollutants in the fluid sample is ed by the porous polymeric material.
27. A method of purifying a fluid sample comprising one or more pollutants, the method comprising ting the fluid sample with the porous ric material of claim 7, whereby at least 50 wt. % of the total amount of the one or more pollutants in the fluid sample is adsorbed by the porous polymeric material.
28. A method of purifying a fluid sample comprising one or more pollutants, the method comprising contacting the fluid sample with the porous polymeric material of claim 11, whereby at least 50 wt. % of the total amount of the one or more pollutants in the fluid sample is adsorbed by the porous polymeric material.
29. A method of purifying a fluid sample sing one or more pollutants, the method comprising contacting the fluid sample with the porous polymeric material of claim 22, whereby at least 50 wt. % of the total amount of the one or more pollutants in the fluid sample is adsorbed by the porous polymeric material.
30. A method of purifying a fluid sample comprising one or more pollutants, the method comprising contacting the fluid sample with the porous polymeric material of claim 24, y at least 50 wt. % of the total amount of the one or more pollutants in the fluid sample is adsorbed by the porous polymeric material. ?x;a? ?x? '1‘ - ‘~ :3}:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NZ817580A NZ817580B2 (en) | 2020-02-13 | Charge-bearing cyclodextrin polymeric materials and methods of making and using same |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201962805505P | 2019-02-14 | 2019-02-14 | |
| NZ778750A NZ778750B2 (en) | 2020-02-13 | Charge-bearing cyclodextrin polymeric materials and methods of making and using same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NZ794050A NZ794050A (en) | 2025-08-29 |
| NZ794050B2 true NZ794050B2 (en) | 2025-12-02 |
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