Kevlar: stiff chains in line

Section 4 of 5

Kevlar is a fibre so strong that layers of its cloth stop bullets. Like nylon, it is a polyamide, its monomers joined by amide links, and its strength comes from the form of its chains.

Kevlar is made from benzene-1,4-diamine, a benzene ring with an -⁠NH₂ group on two opposite corners, and benzene-1,4-dicarboxylic acid, the same acid that makes PET. Each amine group joins an acid group through an amide link, so the chain is benzene rings and amide links taking turns. Factories use a faster-reacting form of the acid, with each -⁠OH swapped for a chlorine atom, so each new link gives off hydrogen chloride, HCl.

p-Phenylenediamine (benzene-1,4-diamine), C₆H₈N₂One of the two monomers of Kevlar. A benzene ring carrying an -NH₂ group on two opposite corners.NH2NH2
Benzene-1,4-diamine: an -⁠NH₂ group on opposite corners of a benzene ring.
Terephthalic acid (benzene-1,4-dicarboxylic acid), C₈H₆O₄The other monomer of PET. A benzene ring carrying a -COOH group on two opposite corners.OHOHOO
Benzene-1,4-dicarboxylic acid: a -⁠COOH group on opposite corners of a benzene ring.

Straight, stiff rods

Every part of Kevlar's chain is flat and stiff. A benzene ring is flat, the atoms of an amide link lie flat in one plane, and each ring joins the chain at opposite corners, so the chain runs straight, like a rod. Nylon's chains have runs of CH₂ groups that twist about their single bonds, so they bend and fold.

Stiff rods line up almost perfectly. Side by side, Kevlar's chains make flat sheets, with each N–⁠H on one chain hydrogen-bonded to a C=O on the next, and the sheets stack on top of each other. The polymer is spun from a solution in concentrated sulfuric acid, and the rods line up as they flow through the spinneret, so the fibre comes out with its chains already in line.

Kevlar's flat chains held side by side by hydrogen bonds Three Kevlar chains lie one above another, each running straight across the drawing. Along each chain, benzene rings drawn as hexagons take turns with amide links: a carbon atom double-bonded to an oxygen atom, joined to a nitrogen atom that carries a hydrogen atom. Each ring joins the chain at opposite corners. The C=O and N-H groups point up and down, toward the neighbouring chains, and dashed hydrogen bonds join each N-H hydrogen to a C=O oxygen on the next chain. NHCOCONHNHCONHCOCONHNHCONHCOCONHNH
Part of a sheet of Kevlar chains. Benzene rings and amide links take turns along each chain, and every N–⁠H hydrogen faces a C=O oxygen on the next chain, joined by a hydrogen bond (dashed).

Strong and heat-proof

To break a Kevlar fibre, a pull has to overcome a great many hydrogen bonds at once, along chains that all point the same way. DuPont, which makes it, puts Kevlar at about five times as strong as steel, weight for weight. It has no melting point: heated, it starts to break down at about 450 °C. Layers of woven Kevlar in body armour catch a bullet and spread its energy over many fibres, and Kevlar also goes into cut-resistant gloves, bicycle tyres, sails and firefighters' clothing.

Quick check

Kevlar and nylon-6,6 both join their monomers with amide links. Why is a Kevlar fibre so much stronger?