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US 10,669,378 B2Granted
Poly(thioethers) for metal ion sequestration
AssigneeRutgers, The State University of New Jersey
InventorsAgostino Pietrangelo, Anshuman Mangalum
Life of this patent
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Abstract
The invention provides a polymer comprising two or more residues of formula III or IV or salts thereof: wherein dash line, X, Y, Q, L, M, n, R1, R2, Ra, Rb, Rc and Rd have any of the values defined in the specification, as well as synthetic intermediates and synthetic methods useful for preparing the compounds. The polymer is useful to treat contaminated water by chelating metal.
Claims15
A polymer comprising two or more residues of formula III or a salt thereof:
- wherein:
- each dash line is independently a single bond or a double bond;
- L is (C1-C6)alkylene, (C2-C6)alkenylene, (C2-C6)alkynylene or arylene, wherein one or more carbon atoms in the alkylene, alkenylene and alkynylene is optionally replaced by —O—, —NH— or —S—, and wherein the alkylene, alkenylene, alkynylene and arylene are optionally substituted by one or more groups selected from halo, hydroxy, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkoxy, hydroxy(C1-C6)alkyl, —NO2, —N(R3)2, —CN, —C(O)—N(R3)2, —O—R3, —S—R3, —O—C(O)—R3, —C(O)—R3, —C(O)—OR3, —N(R3)—C(O)—R3 or —N(R3)—C(O)—N(R3)2;
- Q is (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl or aryl and wherein the alkyl, alkenyl, alkynyl and aryl are optionally substituted by one or more groups selected from halo, hydroxy, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkoxy, hydroxy(C1-C6)alkyl, —NO2, —N(R3)2, —CN, —C(O)—N(R3)2, —O—R3, —S—R3, —O—C(O)—R3, —C(O)—R3, —C(O)—OR3, —N(R3)—C(O)—R3 or —N(R3)—C(O)—N(R3)2;
- Ra is selected from the group consisting of hydrogen, halo, hydroxy, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkoxy, hydroxy(C1-C6)alkyl, —NO2, —N(R3)2, —CN, —C(O)—N(R3)2, —O—R3, —S—R3, —O—C(O)—R3, —C(O)—R3, —C(O)—OR3, —N(R3)—C(O)—R3 and —N(R3)—C(O)—N(R3)2;
- Rb is selected from the group consisting of hydrogen, halo, hydroxy, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkoxy, hydroxy(C1-C6)alkyl, —NO2, —N(R3)2, —CN, —C(O)—N(R3)2, —O—R3, —S—R3, —O—C(O)—R3, —C(O)—R3, —C(O)—OR3, —N(R3)—C(O)—R3 and —N(R3)—C(O)—N(R3)2;
- Rc is selected from the group consisting of hydrogen, halo, hydroxy, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkoxy, hydroxy(C1-C6)alkyl, —NO2, —N(R3)2, —CN, —C(O)—N(R3)2, —O—R3, —S—R3, —O—C(O)—R3, —C(O)—R3, —C(O)—OR3, —N(R3)—C(O)—R3 and —N(R3)—C(O)—N(R3)2;
- Rd is selected from the group consisting of hydrogen, halo, hydroxy, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkoxy, hydroxy(C1-C6)alkyl, —NO2, —N(R3)2, —CN, —C(O)—N(R3)2, —O—R3, —S—R3, —O—C(O)—R3, —C(O)—R3, —C(O)—OR3, —N(R3)—C(O)—R3 and —N(R3)—C(O)—N(R3)2;
- each R3 is independently hydrogen or (C1-C6)alkyl;
- and
- n is 1.
8 more elements
A method to prepare a polymer comprising a residue of formula II or a salt thereof, comprising converting a corresponding polymer comprising a residue of formula IIa:
- to provide the polymer comprising a residue of formula II or a salt thereof, wherein:
- X is —S—, —O— or —NH—;
- Y is —S—, —O—, —NH— or —CH2—;
- R1 is selected from the group consisting of hydrogen, halo, hydroxy, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkoxy, hydroxy(C1-C6)alkyl, —NO2, —N(R3)2, —CN, —C(O)—N(R3)2, —O—R3, —S—R3, —O—C(O)—R3, —C(O)—R3, —C(O)—OR3, —N(R3)—C(O)—R3 and —N(R3)—C(O)—N(R3)2;
- R2 is selected from the group consisting of hydrogen, halo, hydroxy, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkoxy, hydroxy(C1-C6)alkyl, —NO2, —N(R3)2, —CN, —C(O)—N(R3)2, —O—R3, —S—R3, —O—C(O)—R3, —C(O)—R3, —C(O)—OR3, —N(R3)—C(O)—R3 and —N(R3)—C(O)—N(R3)2;
- Ra is selected from the group consisting of hydrogen, halo, hydroxy, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkoxy, hydroxy(C1-C6)alkyl, —NO2, —N(R3)2, —CN, —C(O)—N(R3)2, —O—R3, —S—R3, —O—C(O)—R3, —C(O)—R3, —C(O)—OR3, —N(R3)—C(O)—R3 and —N(R3)—C(O)—N(R3)2;
- Rb is selected from the group consisting of hydrogen, halo, hydroxy, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkoxy, hydroxy(C1-C6)alkyl, —NO2, —N(R3)2, —CN, —C(O)—N(R3)2, —O—R3, —S—R3, —O—C(O)—R3, —C(O)—R3, —C(O)—OR3, —N(R3)—C(O)—R3 and —N(R3)—C(O)—N(R3)2;
- Rc is selected from the group consisting of hydrogen, halo, hydroxy, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkoxy, hydroxy(C1-C6)alkyl, —NO2, —N(R3)2, —CN, —C(O)—N(R3)2, —O—R3, —S—R3, —O—C(O)—R3, —C(O)—R3, —C(O)—OR3, —N(R3)—C(O)—R3 and —N(R3)—C(O)—N(R3)2;
- Rd is selected from the group consisting of hydrogen, halo, hydroxy, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkoxy, hydroxy(C1-C6)alkyl, —NO2, —N(R3)2, —CN, —C(O)—N(R3)2, —O—R3, —S—R3, —O—C(O)—R3, —C(O)—R3, —C(O)—OR3, —N(R3)—C(O)—R3 and —N(R3)—C(O)—N(R3)2;
- R3 is independently hydrogen or (C1-C6)alkyl;
- and
- n is 1.
9 more elements
Dependencies are inferred from the claim text.