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    Chemistry Form 5 Chapter 4

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    Kong Boon Thong

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    Ww Nit 4 O hat is Polymer? 1. Ethene, which is an alkene, is a small molecule that contains acarbon- aatbon double bond, C=C. 2. Ethene is produced from petroleum fractions. 3 The C=C bond causes ethene to be more reactive during a chemical reaction, 4. When ethene reacts, one of the C=C bond breaks and converts into single bond which joins with another ethene molecul. 5. The ethene molecules are called monomers, = 6 So,monomers are defined as small molecules (basic units) that combine ' to form long chain molecules which are called polymers. Cur cyto Paces ae tan 7. When polyethene, PE also called polythene is made, thousands of which are easy to shape and are ethene molecules join together to form a long chain molecule. Guile strong. ‘8. The process of joining monomers together to form polymers is called polymerisation reaction. 9. Poly means many while mer means unit. Therefore, polymer means ‘many unit. 10. Polymersare defined as long chain molecules made froma combination cof many repeating basic units of monomers that join together through a polymerisation reaction. les? | Monomers Polymer gr 42 Bock mi me he wi Source of Polymer 1. Polymers can be classified according to: (2) sources from which they are obtained, either natural materials or synthetic materials. (b) characteristics of thermoplastics, thermosets or elastomers. guy 49 When ehene molecules (©) polymerisation process iter byaddition or condensation reaction. gin toga to Coc bons brook 2 Polymers can be divided into two groups based on sources: Natural andar convert ints sgie bonds polymers and synthetic polymers Natural Polymers 1. Natural polymers are polymers that exist naturally, normally from living organisms. ‘oe Polymersaton | Figure 4.4 Latex consists of natural rubber molecules Figure 4.5 Structure of a fat molecule 321 Powered by CamScanner CHAPTER 4 Polymer 2, Table 4.1 shows examples of natural polymers and their monomers. Table 4.1 Natural polymers and their monomer Starch Glucose Proteins ‘Amino acids Fats Fatty acids and glycerol Natural rubber Isoprene Nucleic acids Nucleotides Cellulose Glucose Synthetic Polymers 1, Synthetic polymers are man-made polymers produced from polymerisation reactions in the laboratory or industry. 2. Monomers are usually obtained from petroleum fractions. 3. Table 42 shows examples of synthetic polymers, their monomers and their main uses. Table 4.2 Examples of synthetic polymers, their monomer and main uses cpolymer [Monomer [Mainuses Polyethene, PE Ethene Plastic bags, bowls, kitchenware, bottles Polypropene Propene Bottles, moulds, battery cases, ropes Polyvinyl chloride (PVC) | Vinyl chloride Pipes, artificial leather goods, gutters, vinyl records _| Polystyrene (Styrofoam) | Styrene (Phenylethene) | Packaging materials, egg trays, toys, heat insulators Polyamide (Nylon) ‘Amide Strings, ropes, fabrics, ish nets, tents Perspex Methyl methacrylate lank oe Ge dnaicans Polyester (Terylene) | Ester Clothes, ropes, nets ‘Photograph 4.1 Nylon ropes ‘Types of Polymers Thermoplastic Polymers. 1. Plastics actually comes from the Greek word “Plastikos” which means able to be shaped or moulded. 2. Thermoplastic polymers also known as thermosoftening plastics are polymers that become soft and thus mouldable when heated and hard when cooled. 3. This process of softening and hardening can be repeated over and cover again. 4. (a) On heating, the polymer chains drift further apart, causing the plastic to soften. (b) On cooling, the chains move closer together and the plastic hardens because there are no links between the polymer chains. (©) The polymer chains do not chemically bond with each other when heated. 322 Powered by CamScanner Figure 4.6 Structure of thermoplastic ® txamples of thermoplastic polymers are polyethene, polyvinyl chloride (PVC), polypropene, polystyrene and nylon. Thermosetting Polymers 1, Also known as a thermoset, a. thermosetting, polymers is a polymer that once set cannot be soften by heating. The process cannot be reversed conce the polymer has hardened. 2. Cross-links between the polymer chains prevent the polymer chains from moving apart when heated. 3. Thermosetting polymers include _bakelite, vulcanised rubber and melamine. 4 When heated strongly, the polymer decomposes. eogog fo foct Govtiong Figure 4.7 Structure of bakelite, a copolymer between methanol and phenol Photograph 4.4 Bakelite product 323 CHAPTER 4 Polymer Photograph 4.5 Melamine resin product Elastomer Polymers 1. An elastomer is a polymer that can be stretched when a force is applied to it. 2. Ie returns to its original shape or length when the force is released. 3. Inother words, elastomer polymers have elasticity properties. 4, A few crosslinks are present between the polymer chains, Otherwise the chains will slide over one another and the polymer will not return to its original state. 5. However, if there are too many cross-links, the polymer will become like a thermosetting polymer. 6. Examples of elastomer polymers are polyurethane and styrene-butadiene rubber (SBR). ‘Thermoplastic polymers te BR ‘Thermosetting polymers Elastomer polymers Figure 4.9 Comparison between the structures of thermoplastic, thermosetting and elastomer polymers Powered by (3 CamScanner CHAPTER 4 Polymer Polymerisation Reaction ‘Addition Polymerisation 1. Addition polymerisation occurs when monomers or their derivatives that have double covalent bonds between two carbon atoms, C=C react with one another. 2. Addition polymerisation produces polymers that consist of only one type of monomer. The polymers are called homopolymers. 4, Some examples of addition polymers are polyethene, polypropene, polychloroethene and perspex. & ANSE Nee INSU Ne ~t aS + ome + C=C + yon + fax * x ‘e H HH HH HH HH HH H Ethene molecules = =-9—= =-9-r =-9-: Polyethene i tet ! i ech eet 8 | A Ht fp Figure 4.10 Addition polymerisation in the production of polyethene Summary, n I-O—zr Condensation Polymerisation 1. Some polymers such as nylons (polyamides) and terylenes (polyesters) are formed by condensation polymerisation. 2. During condensation polymerisation, other products are formed and eliminated, such as water, H,O or hydrogen chloride, HCl. 3. Condensation polymerisation produces polymers from different monomers, usually two different monomers with two different functional groups. The polymer formed is called a copolymer. 4. Nylon is a synthetic polymer known as polyamide. It is produced from two different monomers which are a Photograph 4.6 Nylon and terylene fabrics carboxylic acid and an amine. +nHCl In Hydrochloric acid Figure 4.11 Condensation polymerisation reaction to produce nylon 324 Powered by CamScanner CHAPTER 4 Polymer 5, Terylene, a type of polyester is produced from condensation polymerisation as shown in Figure 412 +nH,0 12-ethanedio! Terephthalicacid Terylene pM) Figure 4.12 Condensation polymerisation reaction to produce terylene Synthesis of nylon Aim | To synthesis nylon and study the properties of nylon | produced Materials Cyclohexane, CzHy4, decanedioyl dichloride, CigHy [CO-(CH)4-CONH-(CH)-NH] + nHCl] Solution B: 1,6-diaminohexane in sodium | 3. Properties of nylon-6,10: hydroxide powder (@) _Nylon-6,10 has lower moisture absorption than 1. 50 cm’ of distilled water is poured into a beaker. nylon 6 oF nylon-6,12. 2. 1.gof sodium hydroxide powder is added and sired () itis stronger than nylon 11, nylon 12 and until it dissolves. nylon-6,12. 3. 3 cm! of 1,6diaminohexane is added and stirred (© Nylon-6,10 retains its room temperature until it dissolves. toughness at low temperatures better than 4. 20cm! of solution A is poured into another beaker. nylon 6 or nylon-6,6. ‘An equal volume of solution B is added carefully. Two (@ Nylon-6,10 has good resistance to most solvents separate layers will form since solution A contains an ‘and to dilute mineral acids. ganic solvent while solution Bis aqueous. 5. The nylon (a white solid) that begins to form at | Conclusion ‘the interface of these two solutions is grasped with | Nylon can be produced through the reaction between fo pair of tweezers. It 1s pulled out of the beaker | 1,6dlaminohexane and decanedioyl dichloride. The slowly and coll it around the glass rod as shown | nylon produced has better properties than other types in Figure 4.13. of nylon, Polymers and the Environment 1. Synthetic polymers are non-biodegradable. They cannot be decomposed by bacteria or other decomposers. 2. The improper disposal of polymers into rivers and seas will cause: (a) clogged drainage systems and flash floods during heavy rain. (b) water pollution. (©) the death of by aquatic organisms which eat them by mistake. 325 Powered by CamScanner CHAPTER 4 Polymer 3. Bottles and polymer containers collect rain water and become breeding places for mosquitoes which cause diseases like dengue. 4. Burning of polymers also releases toxic chemicals such as carbon monoxide gas, CO, hydrogen chloride gas, HCI and hydrogen cyanide gas, HCN into the atmosphere causing acid rain and air pollution. 5. Several ways to overcome the problems are to: (a)_ produce biodegradable synthetic polymers that can be decomposed by bacteria or water. (b) reduce, reuse and recycle the polymers. (©) prevent open burning. ian me —) 1. What are polymers? Give one example of a polymer. 2. Alkenes can form polymers, What type of polymerisation occurs when alkenes form polymers? 3 What are the characteristics of thermoplastic polymers compared to elastomer polymers? 4 Synthetic polyamides are condensation polymers. Synthetic polyamides are made when carboxylic acids react with ‘amines. Name the other substance that is produced in this reaction. 7. The isoprene molecules undergo addition polymerisation to produce polyisoprene. mae Gay nCH,=C-CH=CH, — -FCH,~C=CH-CH,. 1. Rubber is described as materials which show I — I } elastic properties. CHs CH nt 2. Rubber trees or Hevea brasiliensis was introduced Figure 4.15 Formation of polyisoprene from a large ‘number, n of isoprene monomers widely used in our country as it is a vital agricultural product or commodity which is used in the manufacture of a wide range | Characteristics of Natural Rubber of products. Tn ' 4 Ned oe eee | 1. ie ee of natural rubber are shown in so ea Table 4.3 Characteristics of natural rubber 5. Natural rubber is an elastomer as it is elastic (lengthens or changes shape when a force is when the force is removed). . iled rubber molecul 6 bs monocnaliSEa Grete omadifour ork eee diene in IUPAC nomenclature. less ability to return to its original length or shape. Easily ‘The carbon-carbon double oxidised bonds in natural rubber are oxidised easily in the air in the presence of ultraviolet rays. Soft Exist as a soft white solid at 3 room temperature Electrical Good electrical insulator insulator Reactive to. | Can easily reacts with acids, chemicals alkalis and organic solvents ‘Waterproof | Natural rubber is Figure 4.14 Structural formula of isoprene impermeable to water 326 Powered by CamScanner | 2. The elasticity of natural rubber enables it to be used in tyres, | engineering components, balloons, medical tubes and elastic thread. 3. Rubber is an excellent material to make surgical gloves because rratural rubber is a natural polymer which is a covalent compound. 4, Covalent compounds do not dissolve in water. Hence, body fluids and blood cannot penetrate the glove and infect the user. Coagulation of Latex 1. Latex is a white colloidal solution like milk containing rubber particles covered with negatively-charged protein membranes. 2. The negative charges on the surface of the rubber particles repel fone another and thus prevent the particles from combining and coagulating, That is why latex remains in liquid state. 3. By adding acids, such as methanoic acid (formic acid) or ethanoic acid (acetic acid), latex can be coagulated. 4, Whereas by adding alkalis, such as ammonia solution, latex remains asa liquid. 5. Therefore, the acids are known as coagulants and the alkalis are known as anticoagulant for latex. Coagulation Process of Latex 1. When an acid is added to latex, hydrogen ions, H* from the acid eutralise the negative charges on the protein membranes of the rubber particles. Figure 4.18 Bacteria produce acid which coagultes the latex 2. The rubber particles no longer repel each other and can collide with ‘one another. 3. As a result, the rubber particles coagulate or we can say the latex coagulates. 4. The activity of bacteria in the air produces an organic acid called lactic acid. Hence, hydrogen ions, H’ from lactic acid neutralise the negative charges on the protein membranes of the rubber particles. S. Asa result, coagulation of latex still occurs when latex is lft for a few days. Latex Coagulation Prevention 1. When an alkali is added to latex, hydroxide ions, OH” from the alkali neutralise the hydrogen ions, H’ in the acid produced by bacteria. 2. Asa result, the negative charges remain on the surface of the protein membranes and the rubber particles keep on repelling each other. 3. Thus, the coagulation of latex can be prevented by adding an alkali. 327 CCHAPTER4 Polymer Figure 4.16 Latex from rubber trees ‘and uses of natural rubber Figure 4.19 Rubber particles coagulate ‘when acid is added to latex 2g EL Powered by CamScanner CHAPTER 4 Polymer Experiment 4a Coagulation of latex Aim To study the coagulation process in latex and how to prevent coagulation Problem statement Does acid coagulate latex while alkali prevents the coagulation of latex? Hypothesis ‘An acid coagulates latex while an alkali prevents the | ‘coagulation of latex, ‘Variables | (@ Manipulated: Ethanoic acid and ammonia | @) Responding : Coagulation of latex (© Fued Volume of latex: ‘Materials Latex, 1.0 mol dm” ethanoic acid, CHsCOOH, 1.0moldm? ‘ammonia solution, NH Apparatus Beaker. glass rod. dropper, measuring cylinder Procedure 1, Three beakers are labelled as A, B and C. 2. 20 em’ of latex is poured into each beaker. 3. 2. of dijute ethanoic acid, CH{COOH are added into the latex in beaker B, | 8 rats The mixture is stited continuously with a glass tod ‘and the observation is recorded. 2.em? of ammonia solution, NH is added into beaker Cand the observation is recorded. The three beakers are left overnight. The changes that occur are recorded, Results Table 4.4 Tatex coagulates A Latex only slowly. 5 Tatex + due Tatex coagulates cethanole acia rapidly. a Tatex + aqueous | Latex does not ammonio coagulate. Discussion Anacid such as ethanoic acid, CHyCOOH coagulates the latex, 2. An alkali such as aqueous ammonia. NHy does not ‘coagulate latex. An allcali prevents the coagulation of latex, 1 3. Coagulation of latex can occur by itself siowly. Conclusion 1. The hypothesis is accepted. Addition of an acid will coagulate latex while addition of an aikoli will prevent latex from coagulating, |. An organic acid produced by the activity of bactetia iso coagulates latex after the latex is left for a few days. Q) caution eee A es ee IS Ot te oxpertnene yt ar Ze Producing a product from latex Aim To produce a product from latex Materials Latex, ethanoic acid, CH;COOH, water Apparatus Beaker, measuring cylinder, glass rod Procedure 1. About 200 cm? of latex Is measured and poured into «a beaker. $ cm of ethanolc acid is added slowly into the latex. ‘The mixture is stirred with a glass rod. The glass rod is left in the latex for a while to allow @ layer of latex to form on the glass rod. ‘The glass rod is take out from the latex and it 1s allowed to dry. ‘The glass rod Is dipped in the latex again to allow a thicker layer of latex to form. 328 7. ‘Steps 5 to 6 are repeated until the desired thickness 1s obtained. 8, The glass rod is removed from the latex and it is dried for a few days. The layer of dry latex Is stripped from the glass rod to get a rubber tube. Results A soft elastic rubber tube is produced. Discussion 1. The rubber tube needs to be washed. This is to remove the ethanoic acid, CHyCOOH from the glove. If the rubber tube 1s kept for some time, it will tum yellow and become hard and inelastic. This 4s because the rubber will be slowly oxidised by oxygen in the alt. Conclusion X rubber tube can be made @ latex solution, 2. by dipping a glass rod nto Powered by CamScanner vulcanisation of Rubber 1, Natural rubber is soft ad easily oxidised when exposed to the ar for along time. 2. Vuleanisation is a process to improve thr characteristic of natural rubber of cross-links between polymers chains. through the produc 3. Natural rubber can be hardened by: (a) heating it with sulphur, (b) adding metal oxides or peroxides, (©) immersing it in disulphur dichloride solution, 5,Cl, in methylbenzene, C;Hy or (@ irradiation with gamma-ray. CHAPTER 4 Polymer ef Eilat ‘Chars Goodyear (1800 ~ 1860) was an Amofian chemist who ‘dscovered and patented the ‘wlcarisation process in 1844. 4 In the process, sulphur atoms react with the double bonds in natural rubber molecules to form cross-links between the long polymer chains, ~C-S-S~ ls “CHy—O=CH— CH, CH -C=CH— OH, ~ $$ gS Site ] * mai is $6 [CGR OH tHe OH OCHO Nb cobb Ot = Sulphur CHs be oH Figure 4.21 Sulphur cross-links between polymer chains in vulcanised rubber 5. Ifa rubber strip is stretched, the sulphur cross-links will prevent the rubber molecules from sliding over each other. 6. Asa result, vulcanised rubber is more elastic than natural rubber, Aim To produce vulcanised rubber Materials Latex, ethanoic acid, CH;COOH, disulphur dichloride ‘solution, $;Cly in methylbenzene solution, C;Hs Apparatus Glass rod, white tle, beaker, knife, dropper, retort stand, measuring cylinder, lip Procedure 1. 25 cm of latex Is poured into a beaker. 2. 3 to S drops of ethanoic acid, CH,COOH is added ‘using a dropper into the latex and it is stirred using a glass rod. 3. The latex is poured onto a white tile and even out quickly by using the glass rod to get a layer of latex. 4. The latex is left to coagulate and dry fora few days. isso Wt ti uber shot Figure 4.22 A thin layer of latex ‘5S. The rubber sheet formed is cut into two strips of the same size by using a knife. a D Tz, 3 | Vulcanisation of rubber QQ caution sree Disdptur dichloride fs fammabie and has @ pungent sel. Do the experiment in a fume chamber. —— 6. One of the strips is dipped into disulphur dichloride solution, S,Clz in methylbenzene solution, CH for 2 minutes to form a strip of vulcanised rubber. 7. The strip of vulcanised rubber is removed from the solution and dried by hanging them on the retort stand. Results The rubber strip that has been dipped into the solution of disulphur dichloride solution, §,C1, in methylbenzene solution, CyHfy fs tougher, Discussion 1. The natural rubber strip becomes. vulcanised rubber after being dipped into disulphur dichloride, solution, $;Clz in methylbenzene solution, CyHy. 2, The vuleanisation process occurs and vulcanised rubber Is formed. 3. In the vuleanisation process, sulphur atoms from disulphur dichloride cross.iink rubber molecules with strong covalent bonds, This reduces the ability of the chains to slide over one another. 4, Disulphurdichloridesolution, Cla in methylbenzene solution, C)Hy provides sulphur atoms for the ‘vulcanisation proces. Conclusion Vuleanised rubber forms when the natural rubber strip Is dipped into disulphur dichloride solution, $2C12 in ethylbenzene solution, CyH. 329 Powered by CamScanner CHAPTER 4 Polymer Properties of Vulcanised Rubber Comparison between Vulcanised Rubber and Unvulcanised Rubber 1. The presence of the sulphur cross-links affect the properties of vulcanised rubber as shown in Figure 425, ( ) Properties ) Unvulcanised rubber) More j= Number of double bonds Higher l= Melting point c Lower More elastic lox Elasticity t= Less elastic Strong and hard lo Strength and hardness mp Weak and soft ‘More heat resistant lo Resistance to heat — Non-heat resistant ‘More resistant to oxidation |qumm Resistance to oxidation j—_ Not resistant to oxiaion Figure 4.23 Comparison between vulcanised rubber and unvuleanised rubber 2. Too much vulcanisation would make the rubber hard and brittle. 3. Vulcanised rubber is used mainly to make tyres, footwear, mattresses, gloves, elastic bands, tubings, toys and belts. ok Figure 4.24 Uses of vulcanised rubber in daily life Experiment Investigating the elasticity of vulcanised rubber im Vartables To investigate the elasticty of vuloanised rubber and | (a) Manipulated: Vulcanised and unvulcanisad rubber \unvulcanised rubber strips (©) Responding : The elongation of rubber strips when Problem statement the weight is removed 15 vuloanized rubber mote elastic than unvuleanised | (@) Fixed + Mass of weight, size of rubbor stip ie Materials Hypothesis Vuloanised rubber strip. unvulcanised rubber stip. Vuloanised rubber is more elastic than unvulcanised | thread rubber 330 b Powered by ( CamScanner CHAPTER 4 Polymer suiéog cp tetot stand, metre ruler, 60 g weight Bion cp Bee Velie adit proce | aber sp neem 1. Two sips of vuloanised rubber and unvuloanised rubber are hung by using bulldog clips on the retort ae Woot stand. | 2, The initial Jength of the vulcanised rubber stip and unvulcanised rubber are measured and recorded. Figure 4.25 3, AS0g weight s hung on each of the stip. 5. Tho wolghs xe removed and the tal length of 4. The each reading is recorded. each rubber strip is measured again, resus Table 45 Final length after . Stretched length | Increase in length Initiat wolght s removed al Yength (em) | sth weight (em) (em ‘Seam Tavaleenised nibber 75 105 30) 35) ‘ulead nibber 75 35 206) 75 G0 iscuson 1. The increase in length of the vulcanised rubber strip (stretched length) is less thon the increase in length of the unvuloanised rubber strip (that is, B; < Bj). This shows that vuloanised rubber is harder and stronger than ‘unvuloanised nubber. 2. Vuloanised rubber has a greater ability to return to its original length after the weight is taken olf (that i. By < B). ‘Tis shows that the vulconised rubber is more elastic than unvuleanised rubber. Conctusion, 1. The hypothesis is aocepted. 2. Vuloonised rubber is more elostic than unvulcanised rubber, 1 Name the monomer of natural rubber according to IUPAC nomenclature. 2. Write a balanced chemical equation for polymerisation of natural rubber. 3 Explain why vulcanised rubber is more elastic than unvuleanised rubber. (2 4 What causes latex to coagulate under natural conditions? Suggest a method to prevent this phenomenon. (IE Synthetic Rubber 1. Synthetic rubber is a synthetic polymer that is elastic in nature or elastomer polymer. 2. Created in 1909 by Fritz Hofmann, it has a similar structure to natural rubber and is cheaper than natural rubber. 3. Solid synthetic rubber is flexible, durable, hardens when cooled and ms can be moulded when heated. It is also resistant to heat, light an Used as an electrical insulator. ‘4. Depending on the chemicals added and the properties associated ‘with it, synthetic rubber can be as hard asa bowling ball, or as elastic photograph 4.7 Fabric made from as a rubber band or as soft asa sponge. nscerenes «Ge of Pe eee 331 Powered by CamScanner CHAPTER 4 Polymer 5. There are many types of synthetic rubber. Approximately 70% of all rubbers used today are synthetic rubber. Uses of Synthetic Rubber 1. There are about twenty different types of chemicals used for making different synthetic rubbers. 2 Some of the popular synthetic rubbers are polychloroprene, chloroprene rubber (CR)/ neoprene, silicone rubber (SiR), styrene-butadiene rubber (SBR), isoprene rubber (IR), butadiene rubber (BR) and many more. 3. Different types of synthetic rubber have their own characteristics and uses. Neoprene 1. Invented in 1931 by Dupont, neoprene is produced by the polymerisation of chloroprene or 2-chlorobuta-1,3-diene in IUPAC nomenclature. The term diene means that this molecule contains two double bonds. 2. The molecular formula is C,HsCL. Che ae Figure 4.26 1¢ polymer is named polychloroprene or neoprene. 4. Liquid neoprene is colourless, less dense than water, has a pungent smell, is slightly soluble in water and soluble in organic solvents like alcohol and diethyl ether. Photograph 4.8 Neoprene is used to make fvel lines (hoses) for petrol 5. Neoprene is a highly resistant material and is used for a variety of outdoor and marine applications. 332 6. Neoprene is more resistant than natural rubber to water, oils, solvents and heat. 7. Itis flexible over a wide range of temperatures, 8. Cross-links by vulcanisation improve neoprene, The number of sulphur cross-links determines the strength and hardness of neoprene. 9. Neoprene is used to make hoses for petrol, containers for corrosive liquids, sports and medical equipment, laptop covers and sleeves, safety gloves, and gaskets. 10. When heated, neoprene decomposes and emits a toxic gas which is hydrogen chloride. |_ Styrene-butadiene Rubber (SBR) 1. In 1929, a German chemist developed a series of synthetic elastomers by copolymerisation of two monomers (styrene and butadiene) in the presence ofa catalyst. The formula for butadiene is CH;=CH-CH=CH, and the formula for styrene is CH=CH-CH,, 3. The polymer produced is called styrene-butadiene rubber or SBR. SBR consists of 75% butadiene and 25% styrene. * CH=CH, + CH,

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