p-Toluenesulfonic acid monohydrate → Chdmdve

Participants

Reaction Steps

PLA Based Polyacetal Containing Diamino Ester/Caprolactone Adduct Polyacetal(PLA/CHDM/CHDMDVE/phenylalanine ester-caprolactone adduct) was produced using the following procedure: Poly-I-lactic acid diol (4 g, Mn=5200/Mw=10800) and diphenylalanine ester/caprolactone (3.0 g) adducts were placed into a 125 ml glass vial. p-Toluene sulfonic acid monohydrate(16 mg) was added to the vial and the contents dried in a vacuum oven (100 C/4 hr). The vial was then stoppered (silicon stopper/aluminium crimp lid) and 30 ml of anhydrous chloroform was added. This was stirred using a magnetic stirrer at room temperature. The PLA diol was polymerised with (cis/trans) cyclohexane dimethanol divinyl ether (CHDMDVE). A CHDMDVE/anhydrous chloroform solution (2 g/10 ml) was prepared and added in small aliquots. The resulting solution was noted to become cloudy. The solution was then filtered, via a syringe fitted with a 0.45 um nylon filter, into a separated sealed Wheaton vial (125 ml) containing CHDM (1.0 g), magnetic stirrer and p-TSA (10 mg). This formed a clear straw yellow solution. 9 ml of a CHDMDVE/chloroform solution (1.23 g/10 ml chloroform) was added over a 2 hr period. The resulting viscous solution was purified by passing the solution through an Al2O3/glasswool column, precipitating into methanol and dried to remove residual solvent. The polymer structure was confirmed using FTIR and NMR. Polymer rods (approx. 6.0 mm diameter) were produced by packing a PTFE block, containing a 6.2 mm hole, with polymer. The resulting mould was heated at 180 for 10 mins until the polymer had become molten. The molten polymer was then compressed and cooled to form a soft rod which crystallised on cooling.

Provenance & Evidence