Cyclic carbonyl compounds with pendant carbonate groups, preparations thereof, and polymers therefrom
AssigneesInternational Business Machines Corporation, Central Glass Company, Limited
InventorsMasaki Fujiwara, James Lupton Hedrick, Daniel Paul Sanders, Manabu Yasumoto
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Abstract
A one pot method of preparing cyclic carbonyl compounds comprising an active pendant pentafluorophenyl carbonate 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 carbonate group. Using a suitable nucleophile, the pendant pentafluorophenyl carbonate group can be selectively transformed into a variety of other functional groups before or after the ring opening polymerization.
Claims26
A method, comprising:
- forming a mixture comprising i) a first cyclic carbonyl compound comprising a cyclic carbonyl moiety selected from the group consisting of cyclic carbonates, cyclic ureas, cyclic carbamates, cyclic thiocarbamates, cyclic thiocarbonates, and cyclic dithiocarbonates, and a pendant pentafluorophenyl carbonate group, ii) a nucleophile selected from the group consisting of alcohols, amines, and thiols, iii) an optional catalyst, and iv) an optional solvent;
- agitating the mixture, thereby forming a second cyclic carbonyl compound and pentafluorophenol byproduct, wherein the second cyclic carbonyl compound comprises a second functional group formed by a reaction of the pendant pentafluorophenyl carbonate group with the nucleophile, the second functional group selected from the group consisting of carbonates other than pentafluorophenyl carbonate, carbamates, and thiocarbonates.
A method, comprising:
- agitating a first mixture comprising a catalyst, an initiator, an optional accelerator, an optional solvent, and a first cyclic carbonyl compound comprising a pentafluorophenyl carbonate group, thereby forming a ROP polymer by ring opening polymerization of the first cyclic carbonyl compound, the ROP polymer comprising a chain fragment derived from the initiator, and a first polymer chain;
- wherein i) the chain fragment comprises a first backbone heteroatom, the first backbone heteroatom linked to a first end unit of the first polymer chain, the first backbone heteroatom selected from the group consisting of oxygen, nitrogen, and sulfur, ii) the first polymer chain comprises a second end unit comprising a nucleophilic group selected from the group consisting of hydroxy group, primary amine groups, secondary amine groups, and thiol group, and iii) the first polymer chain comprises a first repeat unit, the first repeat unit comprising a) a backbone functional group selected from the group consisting of carbonate, ureas, carbamates, thiocarbamates, thiocarbonate, and dithiocarbonate, and b) a tetrahedral backbone carbon, the tetrahedral backbone carbon being linked to a first side chain comprising a pentafluorophenyl carbonate group.
Dependencies are inferred from the claim text.