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US 8,940,855 B2Granted
Polymers bearing pendant pentafluorophenyl ester groups, and methods of synthesis and functionalization thereof
AssigneeInternational Business Machines Corporation
InventorsJames L. Hedrick, Alshakim Nelson, Daniel P. Sanders
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Abstract
A one pot method of preparing cyclic carbonyl compounds comprising an active pendant pentafluorophenyl ester group is disclosed. The cyclic carbonyl compounds can be polymerized by ring opening methods to form ROP polymers comprising repeat units comprising a side chain pentafluorophenyl ester group. Using a suitable nucleophile, the pendant pentafluorophenyl ester group can be selectively transformed into a variety of other functional groups before or after the ring opening polymerization.
Claims38
A method, comprising:
- forming a first mixture comprising i) a first cyclic carbonyl monomer comprising a pentafluorophenyl ester and a cyclic carbonyl group, the cyclic carbonyl group selected from the group consisting of cyclic carbonate, cyclic urea, cyclic carbamate, cyclic thiocarbonate, cyclic thiocarbamate, and cyclic dithiocarbonate, ii) a nucleophile selected from the group consisting of an alcohol, amine, and thiol, iii) an optional catalyst, and iv) an optional solvent;
- and
- agitating the first mixture at a temperature effective to form a second mixture comprising a second cyclic carbonyl monomer derived from the first cyclic carbonyl monomer without altering the cyclic carbonyl group of the first cyclic carbonyl monomer, wherein the second cyclic carbonyl monomer comprises an amide, an ester and/or a thioester derived from the pentafluorophenyl ester group.
Dependencies are inferred from the claim text.