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Polyester

From Academic Kids

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Polyester_Shirt,_close-up.jpg
Close-up of a polyester shirt
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SEMexample.jpg
SEM picture of a bend in a high surface area polyester fiber with a seven-lobed cross section

Polyester is a category of polymers, or, more specifically condensation polymers, which contain the ester functional group in their main chain. Although polyesters do exist in nature, polyester generally refers to the large family of synthetic polyesters (plastics) which includes polycarbonate and above all polyethylene terephthalate (PET). PET is one of the most important thermoplastic polyesters.

The first synthetic polyester, glycerine phthalate, was used in the First World War for waterproofing. Natural polyesters have been known since around 1830.

Contents

Applications

Liquid crystalline polyesters are among the first industrially used liquid crystalline polymers. In general they have extremely good mechanical properties and are extremely heat resistant. For that reason, they can be used as an abradable seal in jet engines.

Thermosetting polyester resins are commonly used as casting materials, fiberglass laminating resins, and non-metallic auto-body fillers. In such applications, polymerization and cross-linking are initiated through an exothermic reaction involving an organic peroxide, such as methyl ethyl ketone peroxide or benzoyl peroxide.

Abbreviations

Synthesis

Synthesis of polyesters is generally achieved by a polycondensation reaction.

Azeotrope esterification

In this classical method an alcohol and a carboxylic acid react to form a carboxylic ester. To assemble a polymer, the water formed by the reaction must be continually removed by azeotrope distillation.

Alcoholic transesterification

See main article on transesterification.

Below is a generic methanol transesterification, partway through the polymerization reaction. For the initial stage of the reaction, the "oligomer"s are actually monomers, such as dimethyl terephthalate (doubly ester-terminated) and ethylene glycol (doubly alcohol-terminated). Multifunctional monomers (i.e., glycerol) result in cross-linking, and monomers with other than methyl esters will produce other alcohols as a reaction product. Methanol is evaporated to drive this reaction forward.

          O
          \\
           C - OCH3  +  OH[Oligomer2]
          /
[Oligomer1]
<math>\leftrightarrow<math>
          O
          \\
           C - O[Oligomer2]  + CH3OH
          /
[Oligomer1]
(ester-terminated oligomer + alcohol-terminated oligomer)   (larger oligomer + methanol)

Acylation (HCl method)

The acid begins as an acid chloride, and thus the polycondensation proceeds with emission of hydrochloric acid (HCl) instead of water. This method can be carried out in solution or as an enamel.

Silyl method
In this variant of the HCl method, the carboxylic acid chloride is converted with the trimethyl silyl ether of the alcohol component; trimethyl silyl chloride is produced.

Acetate method (esterification)

Silyl acetate method

Ring-opening polymerization

Aliphatic polyesters can be assembled from lactones under very mild conditions, catalyzed anionically, cationically or metallorganically.de:Polyester nl:Polyester ja:ポリエステル pl:Poliester sv:Polyester

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