Polymer Chemistry. Radical Polymerisation

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1 Polymer Chemistry Radical Polymerisation

2 Aims of this part: Monomers for Radical Polymerisation Free Radical Polymerisation PS and PMMA and their applications Controlled Radical Polymerisation Emulsion Polymerisation Anionic + Cationic Polymerisation Polyisoprene Braun, Chedron, Rehann, Ritter, Voit Polymer Synthesis: Theory and Practice, Springer, 5 th Edition, Sections 2.2, 3.1 Lechner, Gehkre, Nordmeier, Makromolekulare Chemie, Springer, 5 th Edition, Sections 3.1, 3.4

3 Overview on the method Chain-growth Polymerisation with Initiation, Propagation, Termination Products are called Polymerisates For each kind of monomers there an optimal way of polymerisation Not all polymerisations work for all polymers! Great variety in functionality (especially radicals tolerate many side units) Not biodegradable (C/H main-chain) Highly used in Industry (35-40% market share, mainly free radical p.) Monomers relatively easily accessible Almost all solvents can be used (Hexane, Acetone, Water, Alcohols, etc.) Robust polymerisation conditions (except for Oxygen)

4 Typical Monomers Vinylic Monomers Acrylates Methacrylates R = H PE R = Me PP R = Cl PVC R = OH PVA R = H PAA R = Me PMA + Many more R = H PMA R = Me PMMA R = EtOH PHEMA + Many esp. ph functional ones Styrenes R = H PS R = p-sulfonate PSS R = p-me PMS Acrylamides R = H PAAm R = ipr Poly- NiPAM Methacrylamides R = H PMAAm No important ones, rarely used Isoprenes No Methyl unit: Polybutadiene 2nd Methyl unit: Polydimethylbutadiene Monomer leads to a statistical mixture of 2 polymers! (catalyst can promote one kind)

5 Free Radical Polymerisation Industrially most important mechanism Fast chain growth in the beginning, Then reach of a plateu Reason: Chain ends die off and new ones grow shorter General Mechanism: Initiation: p u Free radical p. (uncontrolled chain growth) Initiators: AIBN, DBPO, other peroxides Propagation: n n Termination: Reaction with radical extinction

6 Free Radical Polymerisation Molar Mass is governed by Initiator/Monomer ratio Gives broadly distributed polymers + Dispersities around 2 are normal Radical addition is fast range of milliseconds Good for the production of PS, PMMA and LD-PE. LD-PE: Low-Density-Polyethylene the polymer (long branching) + + Long-chain branching prevents dense packing Branches at random position Chain parts can be equally long Short-chain branching: Backbiting through intermediate 6-Ring. Dead end is a defined butyl unit

7 O n O PMMA Poly(methyl)methacrylate (T g C) Methyl unit prevents free rotation in backbone rigid material No conjugated double bonds No vis. light absorption (transparent) Hydrophobic and UV light resistant Long term stability Discovery in early 1930s by 2 independent researchers: 1) Hill & Crawford in England (ICI) Perspex 2) Röhm in Germany Plexiglas (as a pun on plastic glass) 3) Also industrialised by DuPont in the USA Lucite First use was in WWII by both sides: Otto Röhm submarine periscopes and aircraft windshields, canopies, gun turrets,

8 Polystyrene (PS) n Styrene units prevent close packing (atactic) T g of 90 C Benzene rings UV absorbing, but vis transparent Very low flexibility brittle and stiff material Discovered in 1839 by Eduard Simon ( Styroloxyd ) Polystyrene in 1920s Use as foam (packaging material, cups) Plain plastic as rigid (transparent) cups (the ones that break early) Better cups: Acrylnitril-Butadiene- Styrene copolymer (ABS) Styrofoam process: (for Styrofoam or Styropor or similar tradenames) Polymerisation in Pentane to give expandable PS (EPS) pallets Expanding pallets with superheated steam (Removes plasticiser) Pallets expand + Stick together Packaging foam is formed

9 Controlled Radical Polymerisation Aim of all crp Methods: Avoid terminiation and slow down reaction to gain control defined molecular weight and low disperisity Always the principle: Equillibrium between sleeping and active species. p crp (controlled chain growth) Monomer addition cycle goes from range of ms to complete seconds! Reactions are 1000x slower! u Typical methods for crp: Atom Transfer Radical Polymerisation (ATRP) Reversible Addition-Fragmentation Transfer Polymerisation (RAFT) Nitroxide Mediated Radical Polymerisation (NMRP)... Plus a few sub-types of each of them (especially for ATRP)

10 crp: RAFT The growing polymer chains are shuffled between via a transfer agent based on a thiol-thionyl ester and its stable radicals Initiation: Propagation: (can also go via I part!) Advantage: No metal or additive required, less oxygen sensitive than ATRP, better end-group control than ATRP Disadvantage: T > 70 C, Always contains impurity (polymerisation from initiator site), Re-Initiation necessary (but possible) to reach block-copolymer

11 crp: NMRP Largely developed by Craig Hawker (now UCSB) Relies on a breakable C-O(-N), which is formed reversibly Advantage: No Metal additive needed. Easy Reinitiation Disadvantage: High Temperatures required ( > 130 C) Other Nitroxide compounds are known, but need to be synthesised Not commonly used in modern research, no industrial application reported More details at: Chem. Rev. 2001, 101,

12 crp: ATRP Discovered by Krzysztof Matyjaszewski (Cornell University) Relies on an equilibrium between a Cu(I) and Cu(II) species Derived from Atom Transfer Radical Addition from organic chemistry Problem: Copper must not be oxidised (use SET-LRP or Cu wire) Advantage: Works at C, easy fabrication of block-copolymers

13 crp: Enzyme mediated radical polymerisation Developed by Nico Bruns here at the University of Basel (now at AMI Fribourg) Enzymes like Hemoglobin, Laccase and Horseraddish peroxidase (HRP) catalyse ATRP-like reactions in water. Low Dispersity for macrylates Larger disperisities for acrylates Very large dispersity for acrylamides

14 Block-Copolymers crp methods can be reinitiated: Block-Copolymers are possible ATRP and NMRP have a re-initiable chain end (in theory) Initiator Re-Start Low overall dispersity Chains die off Mulitblocks difficult RAFT always gives impurities of homopolymer! Example from ATRP PMPC PMPC-PDPA Self-Assembly PMPC 25 - PDPA 70 O O N Retention time (min)

15 Emulsion Polymerisation Typical industrial procedure for free radical polymerisation Normal emulsion is in water, reversed emulsion in organic solvent contains: Monomer Droplets Surfactant Initiator Polymerisation starts in solvent phase! Surfactant stabilises polymer + monomer Result: Polymer particles dispersed in solvent phase Latex Polymer Particles are of similar size Hexagonal Packing is preferrred Applied for synthetic rubber, some grades of PVC, PS, PMMA and ABS

16 Polymerisation Induced Self-Assembly (PISA) Special way of emulsion polymerisation RAFT dispersion polymerisation Monomer is (just about) soluble, polymer is not! Starting Block is the stabiliser! Typical monomers are HPMA for water and BzMA for Dodecane dx.doi.org/ /ja502843f, J.Am.Chem.Soc. 2014, 136,

17 Cationic Polymerisation Beta-Elimination as side reaction Controlled Polymerisation Dispersities of around 1.1 possible Initiators: Traces of protic acids, lewis acids and few other cations All Nucleophiles interfere with the reaction (Alcohols, Amines, Water, Acids,...) far less versatile than radical polymerisation! X-Group should be Electron Pushing (e.g. +M or +I Effect) Good for: Proylene, Isobutylene, Vinyl Ethers, Methyl-Vinyl-Keton, N- Vinylpyrrolidone, Allyl Chloride, Styrene Done at low temperatures (-100 C and lower) and in solution Always in solution, but limited choice of solvents (nothing protic!)!highly sensitive to impurities, even in the promille region!

18 Anionic Polymerisation Controlled Polymerisation Dispersities of around 1.1 possible Initiators: Hydroxy-ions, tertiary amines, phosphines, org-met compounds All Electrophiles interfere (Protons, Carbocations, other reactive cations...) far less versatile than radical polymerisation! Y-Group should be Electron Withdrawing group (e.g. -M or -I Effect) Good for: (Meth)acrylates, Vinylchloride, Acrylamide, Styrene Done at ambient temperatures (but lower than 100 C) and in solution Usually done in solution, but limited choice of solvents (nothing protic!)!highly sensitive to protic impurities!

19 Polyisprene Anionic copolymerisation with styrene: Thermoplastic elastomers! Polymerisation can give various possible isomers n Radical Polymersation Metallocen Polymerisation a) n-buli b) AIBN n n Anionic in Bulk (Kautschuk) Low with Radical Polymersation Radical Polymersation Differentiation of isomers possible via NMR or IR n Anionic in solution Radical Polymerisation Synthetic rubber Vulcanisation of Kautschuk with Sulfur Then used for elastics, balloons and similar

20 Block-Copolymers through Carbanionic P.

21 Summary Polyesters and Polyamides can also be made via ROP. Nylon 6 and PCL are important examples. NCA-Polymerisation gives Polypeptides and Polypeptoids. Is a highly controlled polymerisation technique that involves no ions. Oligomers of this kind can be reached very clean in solid phase synthesis. ROP of cyclic ethers gives PEG (besides others). PEG is a highly important biomedical polymer (biostable, biocompatible) Polyoxazolines are quasi-polyamides. (Amide in sidechain) Hydrophobicity can be tuned by length of side chain Metathesis polymerisation yields polyolefins with double bond Catalyst can be made tolerant towards a number of reactive groups Radical Ring-Opening Polymerisation yields a polyester, but can tolerate nucleophilic side groups

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