Nylon Rope Trick

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The Nylon Rope TrickInterfacial Nylon Polycondensation

Interfacial Polymerization
Interfacial Polymerization
Advantages
Low Reaction Temperature Rapid Reaction Good Heat Dispersion
H2N (CH2)6 NH2
+

Virginia Tech: Polymer Materials and Interfaces Laboratory

Synthetic Scheme
O Cl C (CH2)8 O C Cl

Hexamethylene Diamine in water 2 NaOH _ 2n HCL

Sebacoyl Chloride in Dichloromethane

Disadvantages
Interface creates conditions that preclude the need for precise 1:1 functional group stoichiometry Reaction byproducts (HCl) diffuse away from interface and are easily separated from polymer
Expense of Acid Chloride Large Quantities of Organic Solvents Used
H N (CH2)6

H O N C Nylon - 6,10 (CH2)8

O C
n

Materials
Hexamethylene Diamine Sebacoyl Chloride Dichloromethane Distilled Water Sodium Hydroxide Acetone

Procedure
In a small beaker, dissolve 0.5 g of sodium hydroxide pellets and 1.0 g hexamethylene diamine in 20 ml distilled water. In a 100 ml beaker, prepare a solution of 1 ml sebacoyl chloride in 25 ml dry methylene chloride. Slowly pour the aqueous solution of diamine/base over the organic solution (sebacoyl chloride/CH2CL2). Be careful when pouring to ensure tat the two-phase system forms two distinct layers.

Procedure (continued)
Note the formation of nylon at the interface. Grasp it with tweezers and gently pull upwards. The nylon continuously forms at the interface as the nylon rope is wound up by attaching it to a takeup screw turned by and electric motor. The nylon rope is washed with a 50/50 (v/v) acetone/water solution to remove any organic solvent/sebacoyl chloride. Then it is washed with water for removal of excess base/diamine. The rope is dried at 30-40C in a vacuum oven.

Reference: P. W. Morgan and S. L. Kwolek, J. Polymer Sci. 40, 299 (1959)

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