You are on page 1of 3

Addition polymerisation

• • • Addition polymerisation = reaction where many small molecules (monomers) join together to make a long chain molecule and nothing else. Addition polymers are usually formed by alkenes undergoing addition reactions with themselves. Some common examples include:
H H C H

ethene

C H

H

C6H5 C H

phenylethene

C H

H

CH3 C COOCH3

methyl 2-propenoate

C H

H

CN C COOCH3

methyl 2-cyanopropenoate

C H

chloroethene

tetrafluoroethene

propene

• • •

Catalysts are used for the polymerisation, and the exact mechanism depends on the catalyst and alkene (it is not electrophilic addition – it is usually catalytic addition). Polyalkenes are inert (although can burn) – this is partly due to the absence of any polar bonds. As they are inert, they are non-biodegradable.

© www.CHEMSHEETS.co.uk

15-Jul-12

Chemsheets A2 025

Condensation polymerisation
• • • Condensation polymerisation = reaction where many small molecules (monomers) join together to make a long chain molecule with a small molecule (often water) also formed. Many natural polymers are condensation polymers, e.g. silk, starch and DNA. The two main types are polyesters and polyamides.

Polyesters
• • Esters are formed on reaction between carboxylic acids and alcohols. Polyesters are formed when dicarboxylic acids react with diols.

O HO C

O C OH HO OH HO

O C

O C OH HO OH

ethane-1,2-diol strong acid or specific enzyme

Terylene (PET) is a good example of a polyester, made as shown below:
O n HO C O C OH + n HO CH2 CH2 OH

benzene-1,4-dicarboxylic acid

ethane-1,2-diol strong acid or specific enzyme

Polyesters are hydrolysed (in the presence of strong acid or a specific enzyme) into their constituent acid and alcohol, so they are bio-degradable. The ester linkage (which is polar) is broken.

© www.CHEMSHEETS.co.uk

15-Jul-12

Chemsheets A2 025

Polyamides
• • • Amides are formed on reaction between carboxylic acids and amines. Polyamides are formed when dicarboxylic acids react with diamines. Polyamides are hydrolysed (in the presence of strong acid or a specific enzyme), so they are bio-degradable. The amide linkage (which is polar) is broken. e.g. nylon-6,6 is a good example of a polyamide, made as shown below:
O n HO C (CH2) 4 O C OH + n H2N (CH2) 6 NH2

hexanedioic acid

hexane-1,6-diamine

strong acid or specific enzyme

e.g. Kevlar (used in bullet-proof vests) is a another good example of a polyamide, made as shown below:
O n H2N NH2 n HO C O C OH

benzene-1,4-diamine

benzene-1,4-dicarboxylic acid

• •

Polyamides are also formed when amino acids react with each other. Nylon-6 is made from the polymerisation of the amino acid 6-aminohexanoic acid.
O n NH2 (CH2) 5 C OH
strong acid or specific enzyme

© www.CHEMSHEETS.co.uk

15-Jul-12

Chemsheets A2 025