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US 8,207,351 B2Granted
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.
Claims25
A composition, comprising:
- a first cyclic carbonyl compound of the general formula (2):
- wherein
- each Y is a divalent radical independently selected from the group consisting of —O —, —S—, —N(H)—, and —N(Q″)-, wherein each Q″ is a monovalent radical independently selected from the group consisting of alkyl groups comprising 1 to 30 carbons, aryl groups comprising 6 to 30 carbons, and the members of the foregoing alkyl and aryl groups substituted with a pentafluorophenyl carbonate group,
- n′ is 0 or an integer from 1 to 10, wherein when n′ is 0, carbons labeled 4 and 6 are linked together by a single bond,
- each Q′ is a monovalent radical independently selected from the group consisting of hydrogen, halides, pentafluorophenyl carbonate group, alkyl groups comprising 1 to 30 carbons, alkene groups comprising 1 to 30 carbons, alkyne groups comprising 1 to 30 carbons, aryl groups comprising 6 to 30 carbons, ester groups comprising 1 to 30 carbons, amide groups comprising 1 to 30 carbons, thioester groups comprising 1 to 30 carbons, urea groups comprising 1 to 30 carbons, carbamate groups comprising 1 to 30 carbons, ether groups comprising 1 to 30 carbons, alkoxy groups comprising 1 to 30 carbons, and the members of the foregoing alkyl, alkene, alkyne, aryl, ester, amide, thioester, urea, carbamate, ether, and alkoxy groups substituted with a pentafluorophenyl carbonate group, and wherein
- one or more Q′ and/or Q″ comprises a pentafluorophenyl carbonate group.
3 more elements
A composition, comprising:
- a first cyclic carbonate compound of the general formula (5):
- wherein
- m and n are each independently 0 or an integer from 1 to 11, wherein m and n cannot together be 0, and m+n is less than or equal to 11,
- R1 is a monovalent radical selected from the group consisting of hydrogen, halides, and alkyl groups comprising 1 to 30 carbons,
- each V′ is monovalent radical independently selected from the group consisting of hydrogen, halides, pentafluorophenyl carbonate group (—OCO2C6F5), alkyl groups comprising 1 to 30 carbons, alkene groups comprising 1 to 30 carbons, alkyne groups comprising 1 to 30 carbons, aryl groups comprising 6 to 30 carbons, ester groups comprising 1 to 30 carbons, amide groups comprising 1 to 30 carbons, thioester groups comprising 1 to 30 carbons, urea groups comprising 1 to 30 carbons, carbamate groups comprising 1 to 30 carbons, ether groups comprising 1 to 30 carbons, alkoxy groups comprising 1 to 30 carbons, and the members of the foregoing alkyl, alkene, alkyne, aryl, ester, amide, thioester, urea, carbamate, ether, and alkoxy groups substituted with a pentafluorophenyl carbonate group, and
- L′ is a single bond or a divalent linking group selected from the group consisting of alkyl groups comprising 1 to 30 carbons, alkene groups comprising 1 to 30 carbons, alkyne groups comprising 1 to 30 carbons, aryl groups comprising 6 to 30 carbons, ester groups comprising 1 to 30 carbons, amide groups comprising 1 to 30 carbons, thioester groups comprising 1 to 30 carbons, urea groups comprising 1 to 30 carbons, carbamate groups comprising 1 to 30 carbons, and ether groups comprising 1 to 30 carbons.
3 more elements
A method, comprising:
- forming a first mixture comprising bis(pentafluorophenyl) carbonate, a catalyst, an optional solvent, and a precursor compound, the precursor compound comprising i) three or more carbons, ii) a first hydroxy group capable of forming a pentafluorophenyl carbonate in a reaction with bis(pentafluorophenyl) carbonate, and iii) two nucleophilic groups independently selected from the group consisting of alcohols, amines, and thiols, the two nucleophilic groups capable of forming a cyclic carbonyl group in a reaction with bis(pentafluorophenyl) carbonate;
- agitating the first mixture, thereby forming a first cyclic carbonyl compound comprising i) a pendant pentafluorophenyl carbonate group and ii) a cyclic carbonyl moiety selected from the group consisting of cyclic carbonates, cyclic ureas, cyclic carbamates, cyclic thiocarbamates, cyclic thiocarbonates, and cyclic dithiocarbonates.
A method, comprising:
- agitating a first mixture comprising i) a precursor compound comprising two or more carbons and three or more hydroxy groups, ii) bis(pentafluorophenyl) carbonate, and iii) a catalyst, thereby forming a first cyclic carbonate compound comprising a pendant pentafluorophenyl carbonate group.
Dependencies are inferred from the claim text.