Condensation Polymers
In condensation polymerisation, monomers with two functional groups join and release a small molecule (H₂O or HCl). Polyesters: diol + dicarboxylic acid (or diacyl chloride), e.g. PET from benzene-1,4-dicarboxylic acid and ethane-1,2-diol, linked by –COO–. Polyamides: diamine + dicarboxylic acid, e.g. nylon-6,6 (hexane-1,6-diamine + hexanedioic acid) and Kevlar, linked by –CONH–; hydrogen bonds between chains give strength. Proteins are natural polyamides. Unlike poly(alkenes), condensation polymers can be hydrolysed at their polar links (acid or alkali), making some biodegradable (e.g. PLA).
Learning objectives
- Describe formation of polyesters and polyamides.
- Draw repeat units and deduce monomers.
- Explain properties using intermolecular forces.
- Explain why condensation polymers can be hydrolysed.
Why can nylon be broken down by hot acid, but poly(ethene) can't?
Core idea
Nylon stockings and Kevlar vests are both polyamides: the same link, different monomers.
Monomers with two functional groups join and lose a small molecule each time. The polar ester or amide links can be hydrolysed, unlike poly(alkenes).
1. Building a repeat unit
- Hexanedioic acid and hexane-1,6-diamine.
- OH from the acid and H from the amine leave as water.
- Two amide links per repeat unit.
of nylon-6,6 repeat unit, C₁₂H₂₂N₂O₂?
- Goal
- .
- Strategy
- Add atomic masses.
- C and H.
- N and O.
Summary
- Polyesters –COO–, polyamides –CONH–.
- Water or HCl lost.
- Hydrolysable; some biodegradable.
- Condensation polymer
- Polymer formed with loss of a small molecule.
- Polyamide
- Polymer with amide links.
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