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A2 CHEMISTRY NOTES - POLYMERS Addition Polymerisation This type of polymerization involves a small _________ with a carbon to carbon _______ bond which opens to form a ______ chain polymer. The conditions under which the polymer is formed can affect the ____________ of the product. Monomer Repeat Unit Name Use Film for packaging H H and bags, toys, Poly(ethene) bottles, coatings C C H H H CH3 C C H H H C6 H5 C C H H H CONH2 C C H H Poly(propene) Poly(styrene) H Cl C C H H n Poly(chloroethene) Polyvinyl chloride PVC poly(propenamide) H OH C C H H Poly(ethenol) n Milk cartons, rope, outdoor carpeting Transparent containers, plastic glasses, styrofoam Pipe and tubing, raincoats, curtains, phonograph records, luggage, floor tiles Thickener and a filler in facial surgery. Is used to make soft contact lenses Makes water soluble laundry bags and liquid detergent capsules. Addition polymers are ___-___________ as the strong C-C bonds are chemically ______. 1 A2 CHEMISTRY NOTES - POLYMERS Condensation Polymerisation A condensation polymer usually involves two __________ monomers with different functional groups. The monomers join elimination a small molecule, such as ______. Monomer A + Monomer B Condensation Polymer + Water Dicarboxylic Acid + Diols O O O n HO-C-R-C-OH n HO-R-OH O Repeat Unit: Repeat Unit: n HO-C-R-C- O-R-OH + n HOH O - C-R- C - O-R-O- Dicarboxylic acids + diamines O O n HO-C-R-C-OH O n H2N-R-NH2 O O O n HO-C-R-C- NH-R- NH2 + n HOH O - C-R- C - HN-R-NH- Amino Acids O O n HO-C-R-OH n HO-C-R-OH O O n HO-C-R- O- C-R-OH + n HOH 2 A2 CHEMISTRY NOTES - POLYMERS Give the reaction and the repeating unit of the condensation polymer formed from: 1, 2-ethanediol and 1, 4 –butanedioic acid 1, 5-diaminopentane (called cadaverine) and 1, 3-methylpropanedioic acid 6 aminohexanoic acid 3 A2 CHEMISTRY NOTES - POLYMERS Nylon-6,6 In nylon, the repeating units contain chains of carbon atoms. There are various different types of nylon depending on the nature of those chains. Nylon-6,6 is made from two monomers each of which contain ___ carbon atoms . One of the monomers is a 6 carbon acid with a -COOH group at each end, __________ acid. The other monomer is a 6 carbon chain with an amino group, NH2, at each end. This is _________________. When these two compounds polymerise, the amine and acid groups combine, each time with the loss of a molecule of ________. Repeat unit . Making nylon-6,6 in the lab In the lab, it is easy to make nylon-6,6 at room temperature using 1,6-diaminohexane and __________________ instead of hexanedioic acid. The only difference is that molecules of _____ are lost rather than molecules of water. Properties and uses of Nylon Properties: Resists wear, tough, strong. It is used in textiles for _________ and __________, a lot of nylon is used to make tyre cords. The fibres are also used in ______, and nylon can be cast into solid shapes for cogs and bearings in machines. Biodegradability The amide links are susceptible to _________ reactions. This is a slow reaction with acids and gives the diol and diacids . The reaction with strong bases to give the diols and ________ of the diacids is much quicker. 4 A2 CHEMISTRY NOTES - POLYMERS Kevlar Kevlar is similar in structure to nylon-6,6 except that instead of the amide links joining chains of carbon atoms together, they join benzene rings. The two monomers are benzene-1,4-dicarboxylic acid and 1,4-diaminobenzene. If you line these up and remove ________ between the -COOH and -NH2 groups in the same way as we did with nylon-6,6, you get the structure of Kevlar: Repeat unit Properties and Uses Kevlar Properties: Resists high temperatures, low thermal conductivity, high tensile _________ and is flame, chemical and cut resistant. Kevlar is a very _______ material - about five times as strong as steel, weight for weight. It is used in bulletproof vests, in composites for boat construction, in lightweight mountaineering ropes, and for lightweight skis and racquets - amongst many other things. Biodegradability The amide links are susceptible to _________ reactions. This is a slow reaction with acids and gives the diol and diacids . The reaction with strong bases to give the diols and ______ of the diacids is much quicker. 5 A2 CHEMISTRY NOTES - POLYMERS Poly(ethylene terephthalate) also called terylene What is a polyester? A polyester is a polymer (a chain of repeating units) where the individual units are held together by ________ linkages. Making polyesters as an example of condensation polymerisation A polyester is made by a reaction involving an acid with two -COOH groups, and an alcohol with two -OH groups. In the common polyester drawn above: The acid is ______________________. The alcohol is _______________. The monomers lose a molecule of water every time an ester linkage is made. Repeat unit Properties of Terylene Polyester fibers like terylene are ________, they are very ________, absorb very little _______ or moisture, do not __________ easily, withstand wear and tear. Thus clothes made from polyester are long lasting. Uses of terylene Terylene, a polyester is used extensively in textile industry to make ________. Biodegradability The ester linkages are susceptible to __________ reactions. This is a slow reaction with acids and gives the ____ and __________ . The reaction with strong bases to give the diols and _______ of the diacids is much quicker. 6