Polymer Chemistry 2011
Nylon (6,6) by condensation polymerization
A solution of 1 mL of adipoyl chloride in 25 mL of carbon tetrachloride (toxic) is placed in a
50 mL glass beaker. 0.55 g (5.2 mmol) of 1,6-hexanediamine and 0.75 g of NaOH are
dissolved in 13 mL of water in a separate 50 mL glass beaker. The solution of diamine is then
carefully run on the top of the adipoyl chloride solution, using a pipette. A polyamide film is
immediately formed at the interface and can be pulled out from the center with tweezers or
clamps and laid over some glass rods; it can now be pulled out continuously in the form of a
hollow thread (see Figure):
Diamine layer
Acyl chloride layer
The polycondensation comes rapidly to a standstill if pulling out is stopped, but immediately
recommences when pulling out is restarted.
The drown-off polyamide thread is thoroughly washed in 50% ethanol or in acetone, and
dried in vacuum at 30 ºC.
All chemical waste should be disposed in separate dedicated waste containers.
Analysis of the polymer.
Determine the yield of the obtained nylon (6,6), record FTIR of the sample, and run a
differential scanning calorimetry to determine Tg and Tm.
Questions/tasks:
1) Make a risk assessment.
2) Wright polymerization reaction scheme, identify the repeating unit.
3) What is the small by-product of the condensation reaction to produce Nylon 6,6?
4) Explain what is happening molecularly at the interface in the following diagram: