1.1 Basic Polymer Chemistry. 1.2 Polymer Nomenclature. 1.3 Polymer Synthesis. 1.4 Chain Growth Polymerization. Polymer =
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1 1.1 Basic Polymer hemistry Polymers are the largest class of soft materials: over 100 billion pounds of polymers made in US each year lassification systems 1.2 Polymer Nomenclature Polymer = Monomer = Polymer = Mechanisms of chain growth Typical physical state? ligomer = Typical physical state? Polymerization = 1.3 Polymer Synthesis Two synthetic methods hain growth/addition polymerization 1.4 hain Growth Polymerization Addition polymerization ne molecule adds to another with no net loss of atoms (high atom economy) Individual steps are typically rapid (msec, sec) Discrete steps Step growth polymerization Propagation rate >> termination rate What happens if the reaction runs longer? Do the chains get longer? Do you just get more chains? 1
2 1.5 hain Growth Polymerization Addition polymerization What s in the polymerization mixture? 1.6 Monomers for hain Growth Polymers form by Defining features Useful monomers for chain growth Monomer Polymer n ( ) n n X X ( X X ) n ethylene propylene styrene vinyl chloride vinyl acetate methyl methacrylate butadiene acrylonitrile l N 1.7 hain Growth Polymerization Mechanisms to link monomers together adical ationic Anionic Transition metal catalysis 2.1 adical Polymerization Three steps to radical polymerization Initiation (1) (2) + Propagation Termination 2
3 Initiation 2.2 adical Polymerization Propagation 2 2 styrene Initiation 2 ead attacks the tail of the next monomer What defines the head? Why would attack the tail preferentially? l vinyl chloride l 2 Propagation Propagation continues until l l l polystyrene polyvinylchloride 2.3 adical Polymerization Termination adical oupling Disproportionation ( abstraction) 2.4 adical Polymerization hain transfer 2.5 adical Polymerization Another termination mechanism back-biting This is a prominent type of branch. Why would this be so? 3
4 2.6 adical Polymerization Another termination process (chloroalkanes) 2.7 adical Polymerization Monomers for radical polymerization ( ) n l l 4 ( ) n l 3 + l 3 l F l l F 2 F l 2 2 ethylene F 1,1-dichloroethylene vinylchloride 1,1,2,2-tetrafluoroethylene N styrene methylmethacrylate acrylonitrile 1,3-butadiene 2.8 adical Diene Polymerization eaction: n ( ) n 1,3-butadiene polybutadiene Mechanism: 2.9 adical Polymerization Accounts for about ½ of all commercial polymerization What polymer structure forms when propylene is subjected to a radical process? (1) 2 (2) (3) + + Ethylene forms high molecular weight polymer but only under extreme conditions why? then (3), (3), (3), etc. Product is highly branched (where do the branches come from?) Is it possible to make linear PE? 4
5 3.1 ationic Polymerization Initiating and propagating species are cations Monomer attributes? 3.2 Anionic Polymerization Initiator and propagating species are anions ationic polymerization of isobutene (2-methylpropene) Initiation Propagation Initiation isobutene or isobutylene Propagation Propagation hain termination ti by loss of + What forms? polyisobutylene 2 styrene N 2 acrylonitrile N 2 N 2 N N polystyrene polyacrylonitrile 3.3 Anionic Polymerization Monomer attributes? 3.4 iving Polymerization What s a living polymer? ther example of monomers? hain termination n 2 n + polystyrene 5
6 andom copolymers 4.1 opolymers 4.2 opolymers ABS = acrylonitrile-butadiene-styrene terpolymer + + N SB (styrene-butadiene rubber) n N + > n ontrol the amount of each monomer that ends up in the polymer? Block copolymers 4.3 opolymers 4.4 Block opolymers Mechanism and process Polybutadiene Polystyrene Styrene-butadiene block copolymer S S S S S B B B S S S S S B B Polybutadiene framework held together (cross-linked) by clusters of polystyrene 6
7 Graft copolymers 4.5 opolymers 5.1 Metal atalyzed Polymerization oordination and Insertion M = r,, Zr, f, V, Fe, o, Ni, Pd, u Styrene-butadiene graft copolymer Styrene polymerization off polybutadiene backbone M 2 3 M 2 3 M ould you graft polybutadiene off a polystyrene backbone? 5.2 Ziegler-Natta atalysis hain Growth Polyethylene (Polyethene) 5.3 Ziegler-Natta atalysis hain Growth Polypropylene (Polypropene) l l 3 2 l l 3 2 l l l l 2 3 l l l 3 l l l l l l l l l
8 l l l 5.4 Ziegler-Natta atalysis l 2 hain Termination with ydrogen 2 Polymer 2 2 l l 2 Polymer Polymer 5.5 Metal omplex atalysis For polypropylene, the metal center can direct the chain growth MAGAEIA If one orientation is preferred. then one polymer structure t is preferred (isotactic) ti isotactic: atactic: l l 2 2 l l syndiotactic: Polyethylene (PE) Types Density (g/cc) DPE igh Density PE 5.7 Ziegler-Natta atalysis Used to make a variety of polymers DPE = high density polyethylene Formed by DPE Properties inear ow Density PE DPE ow Density PE 2 2 n 3 8
9 5.8 Ziegler-Natta atalysis DPE = linear low density polyethylene ow are branches introduced? 5.9 Ziegler-Natta atalysis DPE = linear low density polyethylene mechanism 2 ow is the branch length changed? ow are the number and location of branches controlled? l l 3 2 l l 2 3 l l n 3 l l l l MP atalysis 6.1 Step Growth Polymerization Metathesis M M 2 2 M + ften referred to as condensation polymerization No free radical or ions are necessary eactive functional groups ing pening Metathesis Polymerization M M M Polymer grows in multiple directions 1:1 stoichiometry of functional groups A A + B B A A-B B-A A-B B M M M New bonds formed during step growth polymerization 9
10 6.2 Step Growth Polymerization ften referred to as condensation polymerization Atom efficient? eactions between functional groups Amide (acid and amine) Ester (acid and alcohol) arbonate (alcohol and acid dichloride) Urethane (alcohol and isocyanate) N N 6.3 Step Growth Polymerization Polymerization mixture contains wide distribution of slowly growing oligomers -2 n ( ) 4 + n N ( ) 6 N adipic acid hexamethylenediamine (MDA) Polyamide diacid + diamine ( ) 4 N ( ) 6 N n nylon 6,6 n + n - 22 terephthalic acid ethylene glycol n poly(ethylene terephthalate) Polyester diacid + dialcohol 6.4 Polyamides First synthetic polyamide was poly(hexamethyleneadipamide), now called nylon 6,6 eactants? Mechanism? - n ( ) 4 + N ( ) 6 N 2 n adipic i acid ( 6 ) hexamethylenediamine i ( 6 ) 6.5 Nylon Nomenclature Double-numbered: 6,6 or 6,10 First number = Second number = Single-numbered: 4 or 6 or 12 Number = ( ) 4 N ( ) 6 N n nylon 6,6 molecular weight = 10,000-25,000 n =
11 6.6 Two outes to Polyesters n + n - 2 high terephthalic h acid ethylene glycol l 6.7 Esterification Mechanism Polyester mechanism + + n 2-2 n 3 3 dimethyl terephthalate (DMT) + 2n -2n 3 low n - + ehatlier s Principle 6.8 Dendrimer 6.9 Polycarbonates Polycarbonates are strong, clear plastics arbonate = diester of carbonic acid ptical market (DVD, D s) n 3 + n l -l l dialcohol + dichloride 3 bisphenol A phosgene 3 ( )n 3 11
12 7.1 Thermoset Polymers inear polymers are typically thermoplastic Soften or melt when heated an dissolve (although sometimes with difficulty) in solvents hemistry to form the polymer takes place in the polymerization reactor an be melted and shaped (molded) into finished articles without further chemistry Thermoplastics are a collection of individual chains 7.2 Thermoset Polymers Thermoset polymers are cross-linked hemistry to form the polymer takes place during formation (molding) of the final article The polymer sets-up or hardens within the mold 7.3 Polyurethane eaction of an isocyanate and an alcohol yields a urethane 7.4 Polyurethane Poly(propylene glycol) is formed by base catalyzed ring opening of propylene oxide with propylene glycol (diol) eaction of a diisocyanate and a diol (like polypropylene glycol) gives polyurethane 12
13 7.5 Polyurethane eaction of polypropylene glycol (diol) and toluenediisocyanate gives linear polyurethane 7.6 Polyurethane eaction of a triol and toluenediisocyanate yields a rigid cross-linked polyurethane N N N N 3 trimethylolpropane TDI N N N 3 N Urethane linkage + 3n 3 K glycerol propylene oxide 2 ( 3 3 ) n 3 3 ( ) n 3 3 ( ) n 7.7 Phenol-Formaldehyde Polymers eo Baekeland discovered the polymerization of formaldehyde and phenol to give phenolic resins Primarily used as a wood adhesive 7.8 Two omponent Epoxy esins 1. ow molecular weight polymer with epoxy end groups 2. uring agent Ethylenediamine reacts with epoxy end groups on low molecular l weight polymer N 2 N 2 + X bakelite N X N N X N X X N N 13
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