Phosgene → HCID 178439294, compound

Participants

Reaction Steps

A 500 mL Morton flask was charged with BPA (11.4 g, 50 mmol), methylene chloride (125 mL), distilled water (90 mL) and MTBAC (0.5 g of a 75 wt % solution in water). The pH was adjusted to 7 with 25 wt % NaOH. Phosgene (7.63 g, 76 mmol, 50 mol % excess) was added at 0.5 g/min maintaining the pH at 7 by the addition of the NaOH solution. The pH was raised to 11.5-12 and eugenol siloxane bisphenol (p=19) (1.6 g, 0.9 mmol) was added and the reaction was stirred for 10 min. BPA (11.4 g, 50 mmol) and p-cumylphenol (1.06 g, 5.0 mmol, 5.0 mol %) were then added and the reaction stirred until chloroformates were no longer detected. Triethylamine (200 uL) was added along with eugenol siloxane bisphenol (p=19) (1.6 g, 0.9 mmol) followed by phosgene (6.11 g, 61 mmol) at pH 10.5. The polymer solution was separated from the brine and washed once with 1N HCl and twice with distilled water. The polymer solution was precipitated into boiling water (750 mL) in a blender, washed with water (500 mL) and dried overnight at 110° C. under vacuum. The product copolycarbonate was analyzed by 1H-NMR and shown to have both blocky and random substructures, the relative amounts of the blocky and random substructures being about 50 percent. 1H-NMR established complete incorporation of the eugenol siloxane bisphenol (9.8 wt %). The Tg of the product copolycarbonate was 136° C. and the weight average molecular weight, Mw, was 35,900.

Provenance & Evidence