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21.17:

Types of Step-Growth Polymers: Polyesters

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Organic Chemistry
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JoVE Core Organic Chemistry
Types of Step-Growth Polymers: Polyesters

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Polymers in which the monomers are joined together by an ester bond are called polyesters. Typically, dicarboxylic acids and diols undergo stepwise condensation to yield polyesters. For instance, terephthalic acid and ethylene glycol undergo Fischer esterification and lose water to form poly(ethylene terephthalate), or PET. PET can also be prepared from dimethyl terephthalate and ethylene glycol via a transesterification process with the loss of methanol. Crude PET can be blow-molded to make soft-drink bottles, spun into Dacron fiber, or cast into Mylar film. Dacron fiber is widely used in the textile industry because of its light weight, high strength, and moisture resistance properties. Mylar film is used to manufacture magnetic recording tapes, as it is strong, flexible, and resistant to ultraviolet degradation. Kodel is another polyester prepared by transesterification of dimethyl terephthalate and 1,4-di(hydroxymethyl)cyclohexane. It is generally used by blending it with wool or cotton to reduce stiffness.

21.17:

Types of Step-Growth Polymers: Polyesters

The introduction of polyesters has brought major development to the textile industry. The wrinkle-free behavior of polyester blends has eliminated the need for starching and ironing clothes.

Polyesters are commonly prepared from terephthalic acid and ethylene glycol; the crude product is known as poly(ethylene terephthalate) or PET. However, polyesters are synthesized industrially by transesterification of dimethyl terephthalate with ethylene glycol at 150 °C. The two reactants and the polymer PET are not volatile at this temperature, but the by-product methanol vaporizes from the reaction, thereby driving the reaction to completion.

For PET synthesis, ethylene glycol is obtained by the air-oxidation of ethylene to ethylene oxide, which upon hydrolysis, gives glycol. Terephthalic acid is prepared by the oxidation of p-xylene.

Figure1

The crude PET can be spun into a Dacron fiber, most commonly used in the textile industry as a clothing material. It can also be fabricated into a film called Mylar. These films are used to prepare magnetic recording tape. Thicker Mylar films are used in compact discs. Poly(ethylene terephthalate) is also blow-molded to make plastic bottles used for soft drinks.

Some polyesters are unstable because they get hydrolyzed in the aqueous medium. Such polyesters find applications where slow degradation is required. For example, the copolymer of glycolic acid and lactic acid is used by surgeons in dissolvable sutures. The copolymer gets hydrolyzed within weeks into starting materials, which get metabolized inside the body.

Figure2