O.S([O-])([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]C)(=O)=O.[Na+].[CH2:20]=[C:21]1[CH2:26][CH2:25][O:24][C:22]1=[O:23].C=CC1C=CC=CC=1.C(O)(=[O:38])C=C.S(OOS([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+].[OH-].[Na+]>>[CH2:20]=[C:21]1[CH2:26][CH2:25][O:24][C:22]1=[O:23].[CH:9]([CH:8]=[CH:7][C:6]([OH:5])=[O:38])=[CH:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1To a 100 mL round bottom flask equipped with a magnetic stir bar was added 8.825 g (0.490 mol) water and 0.117 g (4.06×10−4 mol) sodium dodecyl sulfate (20% aqueous solution). The mixture was heated under flowing nitrogen to 73° C., at which time a monomer mixture consisting of 3.079 g (3.14×10−2 mol) α-methylene-γ-butyrolactone, 1.082 g styrene (1.04×10−2 mol) and 0.220 g (3.66×10−3 mol) acrylic acid was added via syringe pump over 130 minutes. After 10 minutes of monomer mixture addition, an aqueous mixture consisting of 16.694 g (0.927 mol) water, 0.269 g (9.33×10−4 mol) sodium dodecyl sulfate (20% aqueous solution), 0.033 g (1.39×10−4 mol) sodium persulfate, and 0.041 g of a 20% aqueous sodium hydroxide solution was added via syringe pump over 130 minutes. After both the monomer and aqueous mixtures were added completely, the emulsion was allowed to stir for an additional 60 minutes, after which the reaction was cooled to room temperature and dried under vacuum under vacuum at 90° C. overnight. Size exclusion chromatography yielded a monomodal peak with a weight average molecular weight of 104 kDa and a polydispersity of 1.96, relative to polystyrene standards. Differential scanning calorimetry showed a single first order transition at approximately 167° C.
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