Methacrylic Acid → N-(p-aminosulfonylphenyl)methacrylamide

Temperature

70 °C

A 500-mL three-necked flask equipped with a stirrer, a condenser and a dropping funnel was charged with 31.0g(0.36 moles) of methacrylic acid, 39.1 g (0.36 moles) of ethyl chloroformate and 200 mL of acetonitrile, and the mixture was stirred under cooling on an ice water bath. 36.4 g (0.36 moles) of triethylamine was dropped to this mixture over about one hour from the dropping funnel. After completion of dropping, the ice water bath was removed, and the mixture was stirred at room temperature for 30minutes. 51.7g(0.30 moles) of p-aminobenzenesulfonamide was added to the reaction mixture, and the mixture was stirred for one hour while warming on an oil bath at 70 ° C. After completion of the reaction, the reaction mixture was thrown into one liter of water while stirring this water; and the resulting mixture was stirred for 30 minutes. This mixture was filtered to take out a deposit, which was then formed into a slurry upon addition of water. This slurry was filtered, and the thus obtained solid was dried to obtain a white solid of N-(p-aminosulfonylphenyl)methacrylamide (yield: 46.9 g). Next, a 20 -mL three-necked flask equipped with a stirrer, a condenser and a dropping funnel was charged with 4.61 g(0.0192 moles) of N-(p-aminosulfonylphenyl)methaciylamide, 2,94 g (0.0258moles) of ethyl methacrylate, 0.80 g (0.0 15 moles) of acrylonitrile, and 20 g of N,N-dimethylacetarnide, and the mixture was stirred while heating on a warm water bath at 65 °C. 0.15 g of “V-65” (manufactured by Wako Pure Chemical Industries, Ltd.) was added to this mixture, and the mixture was stirred under a nitrogen gas stream for 2 hours while keeping at 65° C. To the reaction mixture, a mixture of 4.61 g of N-(p-amino -sulfonylphenyl)methacrylamide, 2,94 g of ethyl methacrylate, 0.80 g of acrylonitrile, N,N-dimethylacetamide, and 0.15 g of “V-65” was further dropped over 2 hours from the dropping funnel. After completion of dropping, the resulting mixture was further stirred at 65° C. for 2 hours. After completion of the reaction, 40 g of methanol was added to the mixture and cooled. The resulting mixture was thrown into two liters of water while stirring this water, and the mixture was stirred for 30 minutes. A deposit was taken out and dried to obtain 15 g of a white solid. The weight average molecular weight (as reduced into polystyrene) of this specified copolymer was measured by gel penneation chromatography and found to be 53,000.

1. customA 500-mL three-necked flask equipped with a stirrer, a condenser and a dropping funnel
2. temperatureunder cooling on an ice water bath
3. customthe ice water bath was removed
4. stirringthe mixture was stirred at room temperature for 30minutes
5. stirringthe mixture was stirred for one hour
6. customAfter completion of the reaction
7. stirringand the resulting mixture was stirred for 30 minutes
8. filtrationThis mixture was filtered
9. customwas then formed into a slurry upon addition of water
10. filtrationThis slurry was filtered
11. customthe thus obtained solid was dried

ORD record

ord-2e51b0b4ea514975859c7276e6140f92

Source dataset

uspto-grants-2008_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07435021B2