In 1928, no one had ever made a synthetic compound with a molecular weight higher than 4,021
atomic mass units. To test this scheme, Carothers challenged his team to use step-growth
polymerization
to break this record and make a molecule with a molecular weight of 6,000.
In 1930 Julian Hill, a member of the Carothers
team did just that. He reacted propylene glycol with hexadecamethylene
dicarboxylic acid.
The product was called polyester 3-16, because propylene glycol has three carbon atoms, and
hexadecamethylene dicarboxylic acid has sixteen carbon atoms. This new material shattered the
old molecular weight record. Its weight was 12,000!
By now DuPont's management was interested in turning research into real profitable products.
One idea they were interested in was synthetic silk. It was hoped that polyester 3-16 would
become synthetic silk. The material could be made into fibers, but it couldn't be made into
clothing. It melted at mildly high temperatures, which meant it couldn't be ironed. It also
dissolved easily in dry cleaning solvents.
Carothers thought about how to make material with a higher melting point that
wouldn't dissolve so easily. The answer he came up with became what
we now call nylon.
The members of Carothers team studied many different polyesters, but strangely they never tried
to make a polyester from terephthalic acid and ethylene glycol while searching for a good
synthetic fiber. The polyester that would have
resulted has a high melting point and doesn't dissolve easily, and it makes excellent fibers.
Poly(ethylene terephthalate, or PET, would be made in the Carothers
lab, sure enough, by Edgar W. Spanagel
in October 1934. But this was only because he was trying to make small
cyclic molecules. He was working on a project that led to the creation
of the first synthetic musk scents.
By this time, DuPont was putting so much effort into developing a good polyamide fiber that
there was no time to investigate this new
polymer
further. It would have to be re-invented several years later by chemists at the Calico Printers Association in the
United Kingdom, a forerunner of Imperial Chemical Industries (ICI). It was named
Terylene¨ and it would become the polyester we're all
familiar with as clothing and soft drink bottles. Ironically, though none of the polyesters
studied by Carothers and his team became useful products, DuPont ended up making PET under
license, which they called Dacron¨.
2. Hounshell, David and Smith, John Kenly, Science & Corporate Strategy, DuPont R&D
1902-1980. Cambridge: Cambridge University Press, 1988.
3. Spanagel, Edgar W. Oral history by John K. Smith, 9 May 1997. Philadelphia: Chemical
Heritage Foundation.
Trying to prove Hermann Staudinger's macromolecular
theory, Wallace Carothers devised a scheme called step-growth
polymerization. He theorized that he could use conventional chemical
reactions to make molecules with extremely high molecular
weights.
References
1. Hermes, Matthew. Enough for One Lifetime: Wallace Carothers, Inventor of Nylon.
Washington, D.C.: American Chemical Society; Philadelphia: Chemical Heritage Foundation, 1996.