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    Food Packaging Materials

    LISTS OF ACCEPTABLE POLYMERS FOR USE IN FOOD PACKAGINGAPPLICATIONS

    Tables 1 to 12 list polymers that have been granted noobjection status by the Food Packaging Materials & IncidentalAdditives Section of the Chemical Health Hazard Assessment

    Division (Food Directorate) for use in food packagingapplications. The polymers are coded and categorized asshown in the following table.

    POLYMER CATEGORIES

    Table No. Polymer Type Code

    1 polyethylenes PE

    2 polypropylenes PP

    3 polystyrenes PS

    4 polyvinyl chlorides PVC

    5 ionomers I6 polyethylene terephthalates PET

    7 polyvinyl acetates PVAc

    8 polycarbonates PC

    9 polyamides PA

    10 polyvinyl alcohols PVOH

    11 polyvinylidene chlorides PVDC

    12 Others O

    For polycarbonate at a glance, click here .

    http://www.hc-sc.gc.ca/food-aliment/cs-ipc/chha-edpcs/e_food_packaging.htmlhttp://www.hc-sc.gc.ca/food-aliment/cs-ipc/chha-edpcs/e_food_packaging.html
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    Polycarbonate, or specifically polycarbonate of bisphenol A, is a clear plastic usedto make shatterproof windows, lightweight eyeglass lenses, and such. GeneralElectric makes this stuff and sells it as Lexan.

    Polycarbonate gets its name from the carbonate groups in its backbonechain. We call it polycarbonate of bisphenol A because it is made frombisphenol A and phosgene. This starts out with the reaction of bisphenol Awith sodium hydroxide to get the sodium salt of bisphenol A.

    The sodium salt of bisphenol A is then reacted with phosgene, a right nastycompound which was a favorite chemical weapon in World War I, to producethe polycarbonate.

    What? You want the gritty details of the reaction? Then click here and youwill not be disappointed.

    http://www.psrc.usm.edu/macrog/plastic.htmhttp://www.psrc.usm.edu/macrog/plastic.htmhttp://www.psrc.usm.edu/macrog/pcsyn.htmhttp://www.psrc.usm.edu/macrog/plastic.htmhttp://www.psrc.usm.edu/macrog/pcsyn.htm
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    Another polymer used for unbreakable windows is poly(methylmethacrylate) .

    Seeing Another Polycarbonate More Clearly

    Up until now, we've been talking about only one polycarbonate, polycarbonate of bisphenol A. But there's another polycarbonate out there, that some of us look atall the time. In fact, some of us, like me, never look at anything without the helpof this polycarbonate. This is the polycarbonate that is used to make ultra-lighteyeglass lenses. For people with really bad eyesight, like me, if the lenses weremade out of glass, they would be so thick that they'd be too heavy to wear. Iknow. I used to have glass lenses. My glasses were so heavy that wearing themgave me a headache. But this new polycarbonate changed all that. Not only is it alot lighter than glass, but it has a much higher refractive index . That means itbends light more than glass, so my glasses don't need to be nearly so thick.

    So what is this wonderful new polycarbonate? It's very different frompolycarbonate of bisphenol A. We make it by starting with this monomer:

    You can see that it has two allyl groups on the ends. These allyl groups havecarbon-carbon double bonds in them. This means they can polymerize by free radical vinyl polymerization . Of course, there are two allyl groups on eachmonomer. The two allyl groups will become parts of different polymer chains.In this way, all the chains will become tied together to form a crosslinked material that looks like this:

    http://www.psrc.usm.edu/macrog/pmma.htmhttp://www.psrc.usm.edu/macrog/pmma.htmhttp://www.psrc.usm.edu/macrog/radical.htmhttp://www.psrc.usm.edu/macrog/radical.htmhttp://www.psrc.usm.edu/macrog/radical.htmhttp://www.psrc.usm.edu/macrog/xlink.htmhttp://www.psrc.usm.edu/macrog/pmma.htmhttp://www.psrc.usm.edu/macrog/pmma.htmhttp://www.psrc.usm.edu/macrog/radical.htmhttp://www.psrc.usm.edu/macrog/radical.htmhttp://www.psrc.usm.edu/macrog/xlink.htm
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    As you can see, the carbonate-containing groups (shown in blue) for thecrosslinks between the polymer chains (shown in red). This crosslinking ismakes the material very strong, so it won't break nearly as easily as glass

    will. This is really important for kids' glasses! If only this stuff had beeninvented when I was a kid!

    There is a fundamental difference in the two types of polycarbonatedescribed here that I should point out. Polycarbonate of bisphenol A is athermoplastic . This means it can be molded when it is hot. But thepolycarbonate used in eyeglasses is a thermoset . Thermosets do not melt,and they can't be remolded. They are used to make things that need to bereally strong and heat resistant.

    For polyethylene at a glance, click here !Polyethylene is probably the polymer you see most in daily life. Polyethylene isthe most popular plastic in the world. This is the polymer that makes grocery

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    bags, shampoo bottles, children's toys, and even bullet proof vests. For such aversatile material, it has a very simple structure, the simplest of all commercialpolymers. A molecule of polyethylene is nothing more than a long chain of carbonatoms, with two hydrogen atoms attached to each carbon atom. That's what thepicture at the top of the page shows, but it might be easier to draw it like thepicture below, only with the chain of carbon atoms being many thousands of atoms long:

    Sometimes it's a little more complicated. Sometimes some of the carbons,instead of having hydrogens attached to them, will have long chains of polyethylene attached to them. This is called branched, or low-density

    polyethylene, or LDPE. When there is no branching, it is called linearpolyethylene, or HDPE. Linear polyethylene is much stronger than branchedpolyethylene, but branched polyethylene is cheaper and easier to make.

    Linear polyethylene is normally produced with molecular weights in therange of 200,000 to 500,000, but it can be made even higher. Polyethylenewith molecular weights of three to six million is referred to as ultra-highmolecular weight polyethylene, or UHMWPE. UHMWPE can be used to makefibers which are so strong they replaced Kevlar for use in bullet proof vests.Large sheets of it can be used instead of ice for skating rinks.

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    Polyethylene is vinyl polymer , made from the monomer ethylene. Here's amodel of the ethylene monomer. It looks like some sort of art nouveau teddybear if you ask me.

    Branched polyethylene is often made by free radical vinyl polymerization. Linear polyethylene is made by a more complicated procedure called Ziegler-Natta polymerization. UHMWPE is made using metallocene catalysispolymerization.

    But Ziegler-Natta polymerization can be used to make LDPE, too. Bycopolymerizing ethylene monomer with a alkyl-branched comonomer such asone gets a copolymer which has short hydrocarbon branches. Copolymerslike this are called linear low-density polyethylene , or LLDPE. BP producesLLDPE using a comonomer with the catchy name 4-methyl-1-pentene, andsells it under the trade name Innovex . LLDPE is often used to make thingslike plastic films.

    http://www.psrc.usm.edu/macrog/vinyl.htmhttp://www.psrc.usm.edu/macrog/radical.htmhttp://www.psrc.usm.edu/macrog/radical.htmhttp://www.psrc.usm.edu/macrog/ziegler.htmhttp://www.psrc.usm.edu/macrog/ziegler.htmhttp://www.psrc.usm.edu/macrog/mcene.htmhttp://www.psrc.usm.edu/macrog/mcene.htmhttp://www.psrc.usm.edu/macrog/copoly.htmhttp://www.psrc.usm.edu/macrog/copoly.htmhttp://www.psrc.usm.edu/macrog/vinyl.htmhttp://www.psrc.usm.edu/macrog/radical.htmhttp://www.psrc.usm.edu/macrog/ziegler.htmhttp://www.psrc.usm.edu/macrog/ziegler.htmhttp://www.psrc.usm.edu/macrog/mcene.htmhttp://www.psrc.usm.edu/macrog/mcene.htmhttp://www.psrc.usm.edu/macrog/copoly.htmhttp://www.psrc.usm.edu/macrog/copoly.htm
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    For polypropylene at a glance, click here !Polypropylene is one of those rather versatile polymers out there. It servesdouble duty, both as a plastic and as a fiber . As a plastic it is used to make thingslike dishwasher-safe food containers. It can do this because it doesn't meltbelow 160 o C, or 320 o F. Polyethylene , a more common plastic, will anneal ataround 100 o C, which means that polyethylene dishes will warp in thedishwasher. As a fiber , polypropylene is used to make indoor-outdoor carpeting,the kind that you always find around swimming pools and miniature golf courses.It works well for outdoor carpet because it is easy to make coloredpolypropylene, and because polypropylene doesn't absorb water, like nylon does.

    Structurally, it is a vinyl polymer , and is similar to polyethylene , only that onevery other carbon atom in the backbone chain has a methyl group attachedto it. Polypropylene can be made from the monomer propylene by Ziegler-Natta polymerization and by metallocene catalysis polymerization .

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    This is what the monomerpropylene really looks like:

    Wanna know more?

    Research is being conducted on using metallocene catalysis polymerizationto synthesize polypropylene. Metallocene catalysis polymerization can dosome pretty amazing things for polypropylene. Polypropylene can be madewith different tacticities . Most polypropylene we use is isotactic . This meansthat all the methyl groups are on the same side of the chain, like this:

    But sometimes we use atactic polypropylene. Atactic means that the methylgroups are placed randomly on both sides of the chain like this:

    However, using special metallocene catalysts it is believed that we can makepolymers which contain blocks of isotactic polypropylene and blocks of atacticpolypropylene in the same polymer chain, as is shown in the picture:

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    This polymer is rubbery, and makes a good elastomer . This is because theisotactic blocks will form crystals by themselves. But because the isotacticblocks are joined to the atactic blocks, each little hard clump of crystallineisotactic polypropylene will be tied together by soft rubbery tethers of atacticpolypropylene, as you can see in the picture on the right.

    To be honest, atactic polypropylene would be rubbery without help from theisotactic blocks, but it wouldn't be very strong. The hard isotactic blocks holdthe rubbery isotactic material together, to give the material more strength.Most kinds of rubber have to be crosslinked to give them strength, but notpolypropylene elastomers.

    Elastomeric polypropylene, as this copolymer is called, is a kind of thermoplastic elastomer . However, until the research is completed, this typeof polypropylene will not be commercially available.

    The polypropylene which you can buy off the shelf at the store today hasabout 50 - 60% crystallinity, but this is too much for it to behave as anelastomer.

    For poly(ethylene terepthalate) at a glance, click here !Polyesters are the polymers, in the form of fibers , that were used back in theseventies to make all that wonderful disco clothing, the kind you see beingmodeled on the right. But since then, the nations of the world have striven to

    develop more tasteful uses for polyesters, like those nifty shatterproof plasticbottles that hold your favorite refreshing beverages, like the blue bottle in thepicture below. So you see, polyesters can be both plastics and fibers . Another

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    place you find polyester is in balloons. Not the cheap ones that you use for waterballoons, those are made of natural rubber . I'm talking about the fancy ones youget when you're in the hospital. These are made of a polyester film made byDuPont called Mylar. The balloons are made of a sandwich, composed of Mylarand aluminum foil. Materials like this, made of two kinds of material, are calledcomposites .

    A special family of polyesters are polycarbonates .

    Polyesters have hydrocarbon backbones which contain esterlinkages, hence the name.

    The structure in the picture is called poly(ethylene terephthalate), or PET forshort, because it is made up of ethylene groups and terephthalate groups(duh!). I realize that terephthalate is not the kind of word most English-speaking mouths are used to saying, but with practice you should be able tosay it with only a slight feeling of awkwardness when it rolls off your tongue.

    The ester groups in the polyester chain are polar, with the carbonyl oxygenatom having a somewhat negative charge and the carbonyl carbon atomhaving a somewhat positive charge. The positive and negative charges of different ester groups are attracted to each other. This allows the estergroups of nearby chains to line up with each other in crystal form, which iswhy they can form strong fibers .

    The inventor who first discovered how to make bottles from PET wasNathaniel Wyeth. He's the brother of Andrew Wyeth the famous painter. Butothers had tried before. Go read this story of someone who may have beenthe first person to try to make a shatterproof bottle .

    Now I'm sure everyone out there is just dying to have two questionsanswered. The first one is:

    Why can't you return plastic soft drink bottles to get a cool nickel per bottle like you could with the old glassbottles?

    And the second one which I'm positive everyone is wondering about is:

    http://www.psrc.usm.edu/macrog/isoprene.htmhttp://www.psrc.usm.edu/macrog/composit.htmhttp://www.psrc.usm.edu/macrog/pc.htmhttp://www.psrc.usm.edu/macrog/fiber.htmhttp://www.psrc.usm.edu/macrog/tiberius.htmhttp://www.psrc.usm.edu/macrog/isoprene.htmhttp://www.psrc.usm.edu/macrog/composit.htmhttp://www.psrc.usm.edu/macrog/pc.htmhttp://www.psrc.usm.edu/macrog/fiber.htmhttp://www.psrc.usm.edu/macrog/tiberius.htm
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    How come peanut butter comes in neato shatterproof jars but jelly doesn't?

    These two riveting questions, as it turns out, have the same answer. The answeris that PET has too low a glass transition temperature , that is the temperature atwhich the PET becomes soft. Now reusing a soft drink bottle requires that thebottle be sterilized before it is used again. This means washing it at really hightemperatures, temperatures too high for PET. Filling a jar with jelly is alsocarried out at high temperatures. Down at your local jelly factory, the stuff isshot into the jars hot, at temperatures which would cause PET to become soft. SoPET is no good for jelly jars.

    PEN Saves the Day!

    There is a new kind of polyester that is just the thing needed for jelly jars andreturnable bottles. It is poly(ethylene naphthalate), or PEN.

    PEN has a higher glass transition temperature than PET. That's thetemperature at which a polymer gets soft. The glass transition temperatureof PEN is high enough so that it can withstand the heat of both sterilizingbottle washing and hot strawberry jelly. PEN is so good at standing the heatthat you don't even have to make the bottle entirely out of it. Just mixingsome PEN in with the old PET gives a bottle that can take the heat a lotbetter than plain old PET.

    In the big plants where they make polyester, its normal to start off with acompound called dimethyl terephthalate. This is reacted with ethylene glycolis a reaction called transesterification . The result is bis-(2-hydroxyethyl)terephthalate and methanol. But if we heat the reaction toaround 210 o C the methanol will boil away and we don't have to worry aboutit anymore.

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    Then the bis-(2-hydroxyethyl)terephthalate is heated up to a balmy 270 o C, andit reacts to give the poly(ethylene terephtalate) and, oddly, ethylene glycol as aby product. Funny, we started off with ethylene glycol.

    If you want to know how all these reactions go down, click here .

    But in the laboratory, PET is made by other reactions. Terephthalic acid andethylene glycol can polymerize to make PET when you heat them with anacid catalyst. It's possible to make PET from terephthoyl chloride andethylene glycol. This reaction is easier, but terephthoyl chloride is moreexpensive than terephthalic acid, and it's a lot more dangerous.

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    There are two more polyesters on the market that are related to PET. There ispoly(butylene terephthalate) (PBT) and poly(trimethylene terephthalate). Theyare usually used for the same type of things as PET, but in some cases theseperform better.

    For polystyrene at a glance, click here !Polystyrene is an inexpensive and hard plastic , and probably only polyethylene ismore common in your everyday life . The outside housing of the computer you are

    using now is probably made of polystyrene. Model cars and airplanes are madefrom polystyrene, and it also is made in the form of foam packaging andinsulation (Styrofoam TM is one brand of polystyrene foam). Clear plastic drinking

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    cups are made of polystyrene. So are a lot of the molded parts on the inside of your car, like the radio knobs. Polystyrene is also used in toys, and the housingsof things like hairdryers, computers, and kitchen appliances.

    Polystyrene is a vinyl polymer . Structurally, it is a long hydrocarbon chain,with a phenyl group attached to every other carbon atom. Polystyrene isproduced by free radical vinyl polymerization , from the monomer styrene.

    This is a better picture of what the monomer styrene looks like:

    Go ahead, play with it!

    Polystyrene is also a component of a type of hard rubber called poly(styrene-butadiene-styrene) , or SBS rubber. SBS rubber is a thermoplastic elastomer .

    The Polystyrene of the Future

    There's a new kind of polystyrene out there, called syndiotactic polystyrene.It's different because the phenyl groups on the polymer chain are attached toalternating sides of the polymer backbone chain. "Normal" or atactic polystyrene has no order with regard to the side of the chain on which thephenyl groups are attached.

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    You can see the new syndiotactic polystyrene alongside the old atacticpolystyrene in 3-D by clicking here . The new syndiotactic polystyrene iscrystalline , and melts at 270 o C.

    But it's a lot more expensive!

    Syndiotactic polystyrene is made by metallocene catalysis polymerization .

    What would happen if we were to take some styrene monomer, andpolymerize it free radically, but let's say we put some polybutadiene rubberin the mix. Take a look at polybutadiene, and you'll see that it has doublebonds in it that can polymerize. We end up with the polybutadienecopolymerizing with the styrene monomer, to get a type of copolymer calleda graft copolymer . This is a polymer with polymer chains growing out of it,and which are a different kind of polymer than the backbone chain. In thiscase, it's a polystyrene chain with chains of polybutadiene growing out of it.

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    These rubbery chains hanging off of the backbone chain do some good thingsfor polystyrene. Polybutadiene and polystyrene homopolymers don't mix,mind you. So the polybutadiene branches try as best they can to phaseseparate, and form little globs, like you see in the picture below. But theselittle globs are always going to be tied to the polystyrene phase. So theyhave an effect on that polystyrene. They act to absorb energy when thepolymer gets hit with something. They give the polymer a resilience thatnormal polystyrene doesn't have. This makes it stronger, not as brittle, andcapable of taking harder impacts without breaking than regular polystyrene.This material is called high-impact polystyrene , or HIPS for short.

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    I'll let you in on a little secret. Not all the chains in HIPS are branched likethis. There are a lot chains of plain polystyrene and plain polybutadienemixed in there, too. This makes HIPS something we call and immiscible blend of polystyrene and polybutadiene. But it is the grafted polystyrene-polybutadiene molecules that make the whole system work by binding thetwo phases (the polystyrene phase and the polybutadiene phase) together.

    For poly(vinyl chloride) at a glance, click here !Poly(vinyl chloride) is the plastic known at the hardware store as PVC. This is thePVC from which pipes are made, and PVC pipe is everywhere. The plumbing inyour house is probably PVC pipe, unless it's an older house. PVC pipe is whatrural high schools with small budgets use to make goal posts for their footballfields. But there's more to PVC than just pipe. The "vinyl" siding used on housesis made of poly(vinyl chloride). Inside the house, PVC is used to make linoleumfor the floor. In the seventies, PVC was often used to make vinyl car tops.

    PVC is useful because it resists two things that hate each other: fire andwater. Because of its water resistance it is used to make raincoats andshower curtains, and of course, water pipes. It has flame resistance, too,because it contains chlorine. When you try to burn PVC, chlorine atoms arereleased, and chlorine atoms inhibit combustion.

    Structurally, PVC is a vinyl polymer . (well, duh!) It is similar to polyethylene ,but on every other carbon in the backbone chain, one of the hydrogen atomsis replaced with a chlorine atom. It is produced by the free radicalpolymerization of vinyl chloride.

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    And here, my friends, is that monomer, vinyl chloride:

    PVC was one of those odd discoveries that actually had to be made twice. Itseems around a hundred years ago, a few German entrepreneurs decidedthey were going to make loads of cash lighting people's homes with lampsfueled by acetylene gas. Wouldn't you know it, right about the time they hadproduced tons of acetylene to sell to everyone who was going to buy theirlamps, new efficient electric generators were developed which made theprice of electric lighting drop so low that the acetylene lamp business wasfinished. That left a lot of acetylene laying around.

    So in 1912 one German chemist, Fritz Klatte decided to try to do somethingwith it, and reacted some acetylene with hydrochloric acid (HCl). Now thisreaction will produce vinyl chloride, but at that time no one knew what to dowith it, so he put it on the shelf, where it polymerized over time. Notknowing what to do with the PVC he had just invented, he told his bosses athis company, Greisheim Electron, who had the material patented in Germany.They never figured out a use for PVC, and in 1925 their patent expired.

    Wouldn't you know it, in 1926 the very next year, and American chemist,Waldo Semon was working at B.F. Goodrich when he independently invented

    PVC. But unlike the earlier chemists, it dawned on him that this new materialwould make a perfect shower curtain. He and his bosses at B.F. Goodrichpatented PVC in the United States (Klatte's bosses apparently never filed fora patent outside Germany). Tons of new uses for this wonderful waterproof material followed, and PVC was a smash hit the second time around.

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    For Nylon 6,6 at a glance, click here !For Nylon 6 at a glance, click here !

    Nylons are one of the most common polymers used as a fiber . Nylon is found inclothing all the time, but also in other places, in the form of a thermoplastic .Nylon's first real success came with its use in women's stockings, in about 1940.They were a big hit, but they became hard to get, because the next year theUnited States entered World War II, and nylon was needed to make warmaterials, like parachutes and ropes. But before stockings or parachutes, thevery first nylon product was a toothbrush with nylon bristles.

    Nylons are also called polyamides, because of the characteristic amidegroups in the backbone chain. Proteins , such as the silk nylon was made toreplace, are also polyamides. These amide groups are very polar, and canhydrogen bond with each other. Because of this, and because the nylonbackbone is so regular and symmetrical, nylons are often crystalline , andmake very good fibers .

    The nylon in the pictures on this page is called nylon 6,6, because each

    repeat unit of the polymer chain has two stretches of carbon atoms, eachbeing six carbon atoms long. Other nylons can have different numbers of carbon atoms in these stretches.

    Nylons can be made from diacid chlorides and diamines. Nylon 6,6 is madefrom the monomers adipoyl chloride and hexamethylene diamine.

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    This is one way of making nylon 6,6 in the laboratory. But in a nylon plant,it's usually made by reacting adipic acid with hexamethylene diamine:

    If you want to know how this works, click here .

    Another kind of nylon is nylon 6. It's a lot like nylon 6,6 except that it onlyhas one kind of carbon chain, which is six atoms long.

    It's made by a ring opening polymerization form the monomer caprolactam. Click

    here to find out more about this polymerization. Nylon 6 doesn't behave muchdifferently from nylon 6,6. The only reason both are made is because DuPont

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    patented nylon 6,6, so other companies had to invent nylon 6 in order to get inon the nylon business.

    For Poly(methyl methacrylate) at a glance, click here !Poly(methyl methacrylate), which lazy scientists call PMMA, is a clear plastic ,used as a shatterproof replacement for glass. The barrier at the ice rink whichkeeps hockey pucks from flying in the faces of fans is made of PMMA. Thechemical company Rohm and Haas makes windows out of it and calls it Plexiglas.Ineos Acrylics also makes it and calls it Lucite. Lucite is used to make thesurfaces of hot tubs, sinks, and the ever popular one piece bathtub and showerunits, among other things.

    When it comes to making windows, PMMA has another advantage over glass.PMMA is more transparent than glass. When glass windows are made toothick, they become difficult to see through. But PMMA windows can be madeas much as 13 inches (33 cm) thick, and they're still perfectly transparent.This makes PMMA a wonderful material for making large aquariums, whosewindows must be thick in order to contain the high pressure millions of gallons of water. In fact, the largest single window in the world, anobservation window at California's Monterrey Bay Aquarium, is made of onebig piece of PMMA which is 54 feet long, 18 feet high, and 13 inches thick(16.6 m long, 5.5 m high, and 33 cm thick).

    PMMA is also found in paint. The painting onyour right, Acrylic Elf was painted by PeteHalverson with acrylic paints. Acrylic "latex"paints often contain PMMA suspended in water.PMMA doesn't dissolve in water, so dispersingPMMA in water requires we use another polymerto make water and PMMA compatible with eachother. To see how we do this, go visit thepoly(vinyl acetate) page.

    But PMMA is more than just plastic and paint.Often lubricating oils and hydraulic fluids tend to get really viscous and evengummy when they get really cold. This is a real pain when you're trying tooperate heavy equipment in really cold weather. But when a little bit PMMAis dissolved in these oils and fluids, they don't get viscous in the cold, andmachines can be operated down to -100 o C (-150 o F), that is, presuming therest of the machine can take that kind of cold!

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    PMMA is a vinyl polymer , made by free radical vinyl polymerization from themonomer methyl methacrylate.

    Aramids are a family of nylons , including Nomex and Kevlar . Kevlar is used to

    make things like bulletproof vests and puncture resistant bicycle tires. I supposeone could even make bulletproof bicycle tires from Kevlar if one felt the need.

    Blends of Nomex and Kevlar are used to make fireproof clothing. Nomex iswhat keeps the monster truck and tractor drivers from burning to deathshould their fire-breathing rigs breathe a little too much fire. Thanks toNomex , an important part of American culture can be practiced safely.(Polymers play another part in the monster truck show in the form of elastomers from which those giant tires are made.) Nomex -Kevlar blendsalso protect fire fighters.

    Kevlar is a polyamide, in which all the amide groups are separated by para -

    phenylene groups, that is, the amide groups attach to the phenyl ringsopposite to each other, at carbons 1 and 4. Kevlar is shown in the big pictureat the top of the page.

    http://www.psrc.usm.edu/macrog/vinyl.htmhttp://www.psrc.usm.edu/macrog/radical.htmhttp://www.psrc.usm.edu/macrog/nylon.htmhttp://www.psrc.usm.edu/macrog/elas.htmhttp://www.psrc.usm.edu/macrog/vinyl.htmhttp://www.psrc.usm.edu/macrog/radical.htmhttp://www.psrc.usm.edu/macrog/nylon.htmhttp://www.psrc.usm.edu/macrog/elas.htm
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    Nomex , on the other hand, has meta- phenylene groups, that is, the amidegroups are attached to the phenyl ring at the 1 an 3 positions.

    Kevlar is a very crystalline polymer. It took a long time to figure out how tomake anything useful out of Kevlar because it wouldn't dissolve in anything.So processing it as a solution was out. It wouldn't melt below a right toasty500 o C, so melting it down was out, too. Then a scientist named Stephanie

    Kwolek came up with a brilliant plan. Click here to find out what it was.

    Aramids are used in the form of fibers . They form into even better fibers thannon-aromatic polyamides, like nylon 6,6 .

    Why? Why?

    Ok, since it seems everyone just has to know, I'll tell you. It has to do with alittle quirky thing that amides do. They have the ability to adopt two differentshapes, or conformations . You can see this in the picture of a low molecularweight amide. The two pictures are the same compound, in two differentconformations. The one on the left is called the trans conformation, and theone on the right is the cis - conformation.

    In Latin, trans means "on the other side". So when the hydrocarbon groupsof the amide are on opposite sides of the amide bond , the bond between thecarbonyl oxygen and the amide nitrogen, it's called a trans - amide. Likewise,cis in Latin means "on the same side", and when both hydrocarbon groupsare on the same side of the amide bond, we call it a cis - amide.

    http://www.psrc.usm.edu/macrog/crystal.htmhttp://www.psrc.usm.edu/macrog/arasyn.htmhttp://www.psrc.usm.edu/macrog/fiber.htmhttp://www.psrc.usm.edu/macrog/nylon.htmhttp://www.psrc.usm.edu/macrog/crystal.htmhttp://www.psrc.usm.edu/macrog/arasyn.htmhttp://www.psrc.usm.edu/macrog/fiber.htmhttp://www.psrc.usm.edu/macrog/nylon.htm
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    The same amide molecule can twist back and forth between the cis - andtrans - conformations, given a little bit of energy.

    The same cis - and trans - conformations exist in polyamides, too. When allthe amide groups in a polyamide, like nylon 6,6 for example, are in the transconformation, the polymer is fully stretched out in a straight line. this isexactly what we want for fibers , because long straight, fully extended chainspack more perfectly into the crystalline form that makes up the fiber. Butsadly, there's always at least some amide linkages in the cis - conformation.So nylon 6,6 chains never become fully extended.

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    But Kevlar is different. When it tries to twist into the cis - conformation, thehydrogens on the big aromatic groups get in the way! The cis conformationputs the hydrogens just a little closer to each other than they want to be. SoKevlar stays nearly fully in the trans - conformation. So Kevlar can fullyextend to form beautiful fibers.

    Now it may help to look at a close-up picture of this. Look at the picturebelow and you can see that when Kevlar tries to form the cis - conformation,there's not enough room for the phenyl hydrogens. So only the trans -conformation is usually found.

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    But there's another polymer that stretches out even better called ultra-highmolecular weight polyethylene . It even replaced Kevlar for making bullet-proof vests!

    For polyacrylonitrile at a glance, click here !Polyacrylonitrile is used for very few products an average consumer would befamiliar with, except to make another polymer, carbon fiber . Homopolymers of polyacrylonitrile have been uses as fibers in hot gas filtration systems, outdoorawnings, sails for yachts, and even fiber reinforced concrete. But mostly

    copolymers containing polyacrylonitrile are used as fibers to make knittedclothing, like socks and sweaters, as well as outdoor products like tents and

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    such. If the label of some piece of clothing says "acrylic", then it's made out of some copolymer of polyacrylonitrile. Usually they're copolymers of acrylonitrileand methyl acrylate, or acrylonitrile and methyl methacrylate :

    Also, sometimes we make copolymers of acrylonitrile and vinyl chloride .These copolymers are flame-retardant, and the fibers made from them arecalled modacrylic fibers.

    But the slew of copolymers of acrylonitrile doesn't stop there. Poly(styrene-co -acrylonitrile) (SAN) and poly(acrylonitrile- co -butadiene- co- -styrene)(ABS), are used as plastics .

    SAN is a simple random copolymer of styrene and acrylonitrile. But ABS is morecomplicated. It's made by polymerizing styrene and acrylonitrile in the presenceof polybutadiene. Polybutadiene has carbon-carbon double bonds in it, which can

    polymerize, too. So we end up with a polybutadiene chain with SAN chainsgrafted onto it, like you see below.

    http://www.psrc.usm.edu/macrog/pmma.htmhttp://www.psrc.usm.edu/macrog/pvc.htmhttp://www.psrc.usm.edu/macrog/plastic.htmhttp://www.psrc.usm.edu/macrog/pmma.htmhttp://www.psrc.usm.edu/macrog/pvc.htmhttp://www.psrc.usm.edu/macrog/plastic.htm
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    ABS is very strong and lightweight. It is strong enough to be usedto make automobile body parts, but it is so light that Wassana canlift this front bumper fascia over her head with only hand! Usingplastics like ABS makes automobiles lighter, so they use less fuel,and therefore they pollute less.

    ABS is a stronger plastic than polystyrene because of the nitrilegroups of its acrylonitrile units. The nitrile groups are very polar, so they areattracted to each other. This allows opposite charges on the nitrile groups tostabilize each other like you see in the picture on the left. This strong

    attraction holds ABS chains together tightly, making the material stronger.Also the rubbery polybutadiene makes ABS tougher than polystyrene.

    Polyacrylonitrile is a vinyl polymer , and a derivative of the acrylate family of polymers. It is made from the monomer acrylonitrile by free radical vinylpolymerization .

    http://www.psrc.usm.edu/macrog/styrene.htmhttp://www.psrc.usm.edu/macrog/vinyl.htmhttp://www.psrc.usm.edu/macrog/acrylate.htmhttp://www.psrc.usm.edu/macrog/radical.htmhttp://www.psrc.usm.edu/macrog/radical.htmhttp://www.psrc.usm.edu/macrog/styrene.htmhttp://www.psrc.usm.edu/macrog/vinyl.htmhttp://www.psrc.usm.edu/macrog/acrylate.htmhttp://www.psrc.usm.edu/macrog/radical.htmhttp://www.psrc.usm.edu/macrog/radical.htm
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    For cellulose at a glance, click here !Cellulose is one of many polymers found in nature. Wood, paper, and cotton allcontain cellulose. Cellulose is an excellent fiber . Wood, cotton, and hemp ropeare all made of fibrous cellulose. Cellulose is made of repeat units of themonomer glucose. This is the same glucose which your body metabolizes in orderto live, but you can't digest it in the form of cellulose. Because cellulose is built

    out of a sugar monomer, it is called a polysaccharide.

    Now take a look at glucose in 3-D!

    Cellulose has an important place in the story of polymers because it wasused to make some of the first synthetic polymers, like cellulose nitrate ,cellulose acetate , and rayon . Click here to find out more.

    Clean hair

    Another cellulose derivative is hydroxyethylcellulose. It differs from plain ol'

    regular cellulose in that some or all of the hydroxyl groups (shown in red) of the

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    glucose repeat unit have been replaced with hydroxyethyl ether groups (shownin blue).

    These hydroxyethyl groups get in the way when the polymer tries tocrystallize . Because it can't crystallize, hydroxyethylcellulose is soluble inwater. In addition to being a great laxative, it's used to thicken shampoos aswell. It also make the soap in the shampoo less foamy, and it helps theshampoo clean better by forming colloids around dirt particles.

    Normally, particles of dirt are insoluble in water. But a chain of hydroxyethylcellulose (shown in blue) can wrap itself around a dirt particle(shown in red). This mass can be thought of as a snack cake, with thepolymer chain as the cake and the dirt as the creamy filling. This snack cakeis soluble in water, so by wrapping around the dirt like this, the

    hydroxyethylcellulose tricks the water into accepting the dirt. In this way,the dirt gets washed away instead of being deposited back onto your hair.

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    Starch is important because we eat it! Starch is found in potatoes,and in grains such as corn and wheat. Starch is made up of glucose repeat units.

    Click on the glucose to see it in 3-D.

    In your body, special proteins called enzymes (which are also polymers, bythe way) break starch down into glucose, so your body can burn it forenergy. If you're eating a healthy diet, you get most of your energy fromstarch in this way.

    Because it is made of sugar molecules it is called a polysaccharide. It is verysimilar to cellulose . To see just how the two are different, click here .

    Starch has a few other uses other than food. It's used inpressing clothes to keep them from wrinkling. It's also used

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    to make a foam packing. Starch is biodegradable, so starch foam packing isan environmentally-friendly alternative to styrofoam packing. But be careful!Entropy, the black labrador retriever on the right, likes to eat starch packing,so don't turn your back on her if you've got a box of it around!

    Polyurethanes are the most well known polymers used to make foams. If you're sitting on a padded chair right now, the cushion is more than likelymade of a polyurethane foam. Polyurethanes are more than foam.

    Much more than foam!

    Polyurethanes are the single most versatile family of polymers there is.

    Polyurethanes can be elastomers , and they can be paints. They can be fibers ,and they can be adhesives. They just pop up everywhere. A wonderfullybizarre polyurethane is spandex .

    Of course, polyurethanes are called polyurethanes because in theirbackbones they have a urethane linkage.

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    The picture shows the a simple polyurethane, but a polyurethane can be anypolymer containing the urethane linkage in its backbone chain. Moresophisticated polyurethanes are possible, for example:

    Polyurethanes are made by reacting diisocyanates with di-alcohols. To findout how, click here .

    Sometimes, the dialcohol is replaced with a diamine, and the polymer we getis a polyurea, because it contains a urea linkage, rather than a urethane

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    linkage. But these are usually called polyurethanes, because they probablywouldn't sell well with a name like polyurea.

    Polyurethanes can hydrogen bond very well, and thus can be very crystalline.For this reason they are often used to make block copolymers with softrubbery polymers. These block copolymers have properties of thermoplasticelastomers .

    Spandex

    One unusual polyurethane thermoplastic elastomer is spandex, which DuPont sellsunder the trade name Lycra. It has both urea and urethane linkages in its backbone.What gives spandex its special properties is the fact that it has hard and soft blocksin its repeat structure. The short polymeric chain of a polyglycol, usually about fortyor so repeats units long, is soft and rubbery. The rest of the repeat unit, you know,the stretch with the urethane linkages, the urea linkages, and the aromatic groups,is extremely rigid. This section is stiff enough that the rigid sections from differentchains clump together and align to form fibers . Of course, they are unusual fibers,as the fibrous domains formed by the stiff blocks are linked together by the rubbery

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    soft sections. The result is a fiber that acts like an elastomer ! This allows us tomake fabric that stretches for exercise clothing and the like.

    Codes Descriptions Properties PackagingApplications

    RecycledProducts

    PolyethyleneTerephthalate(PET, PETE).PET is clear,tough, and has

    good gas andmoisturebarrier properties.Commonlyused in softdrink bottlesand manyinjectionmoldedconsumer productcontainers.

    Other applicationsincludestrapping andboth food andnon-foodcontainers.Cleaned,recycled PETflakes andpellets are ingreat demandfor spinning

    fiber for carpetyarns,producingfiberfill andgeo-textiles.Nickname:Polyester.

    Clarity, strength,toughness,barrier to gas andmoisture,resistance to heat

    Plastic soft drink,water, sports drink,beer, mouthwash,catsup and saladdressing bottles.

    Peanut butter,pickle, jelly and jam jars. Ovenable filmand ovenableprepared food trays.

    Fiber, tote bags,clothing, film and sheet,food and beveragecontainers, carpet,strapping, fleece wear,

    luggage and bottles.

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    High DensityPolyethylene(HDPE). HDPEis used tomake bottlesfor milk, juice,

    water andlaundryproducts.Unpigmentedbottles aretranslucent,have goodbarrier properties andstiffness, andare well suitedto packagingproducts with ashort shelf lifesuch as milk.BecauseHDPE hasgood chemicalresistance, it isused for packagingmanyhousehold andindustrialchemicalssuch asdetergents andbleach.PigmentedHDPE bottleshave better stress crackresistance thanunpigmentedHDPE bottles.

    Stiffness,strength,toughness,resistance tochemicals andmoisture,

    permeability togas, ease of processing, andease of forming.

    Milk, water, juice,cosmetic, shampoo,dish and laundrydetergent bottles;yogurt andmargarine tubs;

    cereal box liners;grocery, trash andretail bags.

    Liquid laundrydetergent, shampoo,conditioner andmotor oil bottles;pipe, buckets,crates, flower pots,garden edging, filmand sheet, recyclingbins, benches, doghouses, plasticlumber, floor tiles,picnic tables,fencing.

    Vinyl (PolyvinylChloride or PVC): Inaddition to itsstable physicalproperties,PVC hasexcellentchemicalresistance,goodweatherability,flowcharacteristicsand stableelectrical

    properties. Thediverse slate of vinyl products

    Versatility, clarity,ease of blending,strength,toughness,resistance togrease, oil andchemicals.

    Clear food and non-food packaging,medical tubing, wireand cable insulation,film and sheet,constructionproducts such aspipes, fittings, siding,floor tiles, carpetbacking and windowframes..

    Packaging, loose-leaf binders, decking,paneling, gutters, mudflaps, film and sheet,floor tiles and mats,resilient flooring,cassette trays, electricalboxes, cables, trafficcones, garden hose,mobile home skirting.

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    can be broadlydivided intorigid andflexiblematerials.Bottles and

    packagingsheet aremajor rigidmarkets, but itis also widelyused in theconstructionmarket for suchapplications aspipes andfittings, siding,carpet backingand windows.Flexible vinyl isused in wireand cableinsulation, filmand sheet,floor coveringssyntheticleather products,coatings, bloodbags, medicaltubing andmany other applications.Low DensityPolyethylene(LDPE).Usedpredominately infilm applications dueto its toughness,flexibility andrelativetransparency,making it popular for use in applicationswhere heat sealingis necessary. LDPEis also used tomanufacture someflexible lids andbottles and it is usedin wire and cableapplications

    Ease of processing,strength,toughness,flexibility, ease of sealing, barrier tomoisture.

    Dry cleaning, breadand frozen foodbags, squeezablebottles, e.g. honey,mustard.

    Shipping envelopes,garbage can liners, floor tile, furniture, film andsheet, compost bins,paneling, trash cans,landscape timber,lumber

    Polypropylene (PP).Polypropylene hasgood chemicalresistance, is

    strong, and has ahigh melting point

    Strength,toughness,resistance toheat, chemicals,

    grease and oil,versatile, barrier

    Catsup bottles,yogurt containersand margarine tubs,medicine bottles

    Automobile batterycases, signal lights,battery cables, brooms,brushes, ice scrapers,

    oil funnels, bicycleracks, rakes, bins,

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    making it good for hot-fill liquids. PP isfound in flexible andrigid packaging tofibers and largemolded parts for

    automotive andconsumer products.

    to moisture. pallets, sheeting, trays.

    Polystyrene (PS).Polystyrene is aversatile plastic thatcan be rigid or foamed. Generalpurpose polystyreneis clear, hard andbrittle. It has arelatively lowmelting point.Typical applicationsinclude protectivepackaging,containers, lids,cups, bottles andtrays.

    Versatility,insulation, clarity,easily formed

    Compact disc jackets, food serviceapplications, grocerystore meat trays,egg cartons, aspirinbottles, cups, plates,cutlery.

    Thermometers, lightswitch plates, thermalinsulation, egg cartons,vents, desk trays, rulers,license plate frames,foam packing, foamplates, cups, utensils

    Other. Use of thiscode indicates thatthe package inquestion is madewith a resin other than the six listedabove, or is made of

    more than one resinlisted above, andused in a multi-layer combination.

    Dependent onresin or combination of resins

    Three and fivegallon reusablewater bottles, somecitrus juice andcatsup bottles.

    Bottles, plastic lumber applications.

    DISCLAIMER

    APC MAKES NO WARRANTY, EXPRESS OR IMPLIED, RESPECTING THE ACCURACYOR COMPLETENESS OF THE INFORMATION PROVIDED HEREIN INCLUDING BUT NOTLIMITED TO IMPLIED WARRANTIES OF MERCHANTABILITY OR FITNESS FOR APARTICULAR USE OR PURPOSE. APC SHALL NOT BE RESPONSIBLE FOR ANYDIRECT, INDIRECT, INCIDENTAL OR CONSEQUENTIAL DAMAGES, DAMAGES FROMLOSS OF USE OR PROFITS, OR COST OF PROCUREMENT OF SUBSTITUTE GOODSOR SERVICES, IN CONTRACT, TORT OR OTHERWISE ARISING OUT OF GOODS OR INCONNECTION WITH THE INFORMATION CONTAINED HEREIN. RECYCLING OFPLASTICS MAY NOT BE AVAILABLE EVERYWHERE. CHECK TO SEE IF PLASTICSRECYCLING IS AVAILABLE IN YOUR COMMUNITY.