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Chemistry · Ch 6 — Polymers

Polyester: Terylene (Dacron)

6.5

Polyester: Terylene (Dacron)

Polyesters are condensation polymers in which the repeating linkage joining the monomer units is an ester group, −CO–O−-\text{CO--O}-, formed by the reaction of a carboxylic acid group with a hydroxyl (alcohol) group, releasing a molecule of water at each linkage -- the same condensation logic used for nylon-6,6's amide linkages, but built from a diol and a diacid instead of a diamine and a diacid.

Terylene (marketed in some countries as Dacron, and known generically as PET, polyethylene terephthalate) is the polyester prescribed by name in this syllabus. It is manufactured by heating ethylene glycol, HO–CH2CH2–OH\text{HO--CH}_2\text{CH}_2\text{--OH} (a diol), with terephthalic acid, p-HOOC–C6H4–COOHp\text{-HOOC--C}_6\text{H}_4\text{--COOH} (a benzene-1,4-dicarboxylic acid, a diacid), in the presence of a catalyst such as zinc acetate/antimony trioxide, at around 420420--460 K460\ \text{K}. At each step one −OH-\text{OH} of the glycol condenses with one −COOH-\text{COOH} of the diacid to form an ester linkage and release water:

n HO–CH2CH2–OH+n p-HOOC–C6H4–COOH→[−O–CH2CH2–O–CO–C6H4–CO–]n+2n H2On\,\text{HO--CH}_2\text{CH}_2\text{--OH} + n\,p\text{-HOOC--C}_6\text{H}_4\text{--COOH} \rightarrow \big[-\text{O--CH}_2\text{CH}_2\text{--O--CO--C}_6\text{H}_4\text{--CO--}\big]_n + 2n\,\text{H}_2\text{O}

giving the repeat unit [−O–CH2CH2–O–CO–C6H4–CO–]n\big[-\text{O--CH}_2\text{CH}_2\text{--O--CO--C}_6\text{H}_4\text{--CO--}\big]_n, in which the rigid, flat benzene ring of the terephthalate unit alternates with the flexible two-carbon glycol bridge along the chain. …