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US 11,390,721 B2Granted
Regioselective C-H xanthylation as a platform technology for polymer functionalization
AssigneeThe University of North Carolina at Chapel Hill
InventorsErik Alexanian, Frank Albert Leibfarth, Jill Williamson, Will Czaplyski
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Abstract
The subject matter described herein relates to methods for polymer xanthylation and the xanthylated polymers produced by such methods. Subsequent replacement of the xanthylate moiety allows facile entry into functionalized polymers.
Claims28
A method for xanthylating a polymer, comprising:
- contacting a polymer selected from the group consisting of polyolefins, polycarbonates, and polyesters with a compound of Formula I
- wherein,
- R1 is aryl, heteroaryl, —COR4, or —SO2R4,
- wherein said aryl or heteroaryl is optionally substituted, and
- wherein R4 is optionally substituted linear or branched C1-6 alkyl, aryl, heteroaryl, cycloalkyl, or heterocycloalkyl;
- R2 is optionally substituted linear or branched C1-6 alkyl, aryl, heteroaryl, cycloalkyl, or heterocycloalkyl;
- R3 is optionally substituted linear or branched C1-6 alkyl, aryl, or heteroaryl;
- and
- X is a bond, —O—, —S—, or —NR5, wherein R5 is optionally substituted linear or branched C1-6 alkyl;
- to form a xanthylated polymer.
7 more elements
A xanthylated polymer comprising at least one structural unit of Formula II
- wherein,
- y is an integer with a value between 1 and 1,000,000;
- R6 is a bond, or substituted linear or branched C1-15 alkyl;
- R7 is absent or present, and when present is hydrogen or substituted linear or branched C1-15 alkyl;
- X is a bond, —O—, or —S—;
- R3 is optionally substituted linear or branched C1-6 alkyl, aryl, or heteroaryl;
- A is a repeat unit of a polymer covalently bound to the xanthate, selected from the group consisting of
- R8, R9, R10, R11, R12, R13, R14, and R15 in each instance, are absent or present, and when present are independently selected from the group consisting of hydrogen and optionally substituted linear or branched C1-15 alkyl;
- L and L′ are each independently a bond or O;
- J, G, Q, and T are independently selected from the group consisting of carbon, oxygen, (C═O), arene, and cycloalkane;
- d, e, m and p, in each instance, are independently an integer between 0 and 20;
- wherein at least one of d, e, m, and p is other than 0;
- at least one of J, G, Q, and T is a carbon covalently bound to R6;
- and
- wherein the wavy line denotes the point of attachment of R6 to the polymer backbone.
12 more elements
A xanthylated polymer comprising at least one structural unit of Formula II
- wherein,
- y is an integer with a value between 1 and 1,000,000;
- R6 is a bond, or substituted linear or branched C1-15 alkyl;
- R7 is absent or present, and when present is hydrogen or substituted linear or branched C1-15 alkyl;
- X is —NR5, wherein R5 is optionally substituted linear or branched C1-6 alkyl;
- R3 is aryl or heteroaryl;
- A is a repeat unit of a polymer covalently bound to the xanthate, selected from the group consisting of
- R8, R9, R10, R11, R12, R13, R14, and R15 in each instance, are absent or present, and when present are independently selected from the group consisting of hydrogen and optionally substituted linear or branched C1-15 alkyl;
- L and L′ are each independently a bond or O;
- J, G, Q, and T are independently selected from the group consisting of carbon, oxygen, (C═O), arene, and cycloalkane;
- d, e, m and p, in each instance, are independently an integer between 0 and 20;
- wherein at least one of d, e, m, and p is other than 0;
- at least one of J, G, Q, and T is a carbon covalently bound to R6;
- and
- wherein the wavy line denotes the point of attachment of R6 to the polymer backbone.
12 more elements
Dependencies are inferred from the claim text.