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<title>Anionic addition polymerization</title>

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Anionic addition polymerization

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<div class="quotebox-title" style=""><a href="International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">IUPAC</a> definition</div>

anionic polymerization: An ionic polymerization in which the kinetic-chain carriers are anions.

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In <a href="Polymer_chemistry" title="Polymer chemistry">polymer chemistry</a>, anionic addition polymerization is a form of <a href="Chain-growth_polymerization" title="Chain-growth polymerization">chain-growth polymerization</a> or addition polymerization that involves the <a href="Polymerization" title="Polymerization">polymerization</a> of <a href="Monomer" title="Monomer">monomers</a> initiated with <a href="Anion" class="mw-redirect" title="Anion">anions</a>. The type of reaction has many manifestations, but traditionally <a href="Vinyl_group" title="Vinyl group">vinyl</a> monomers are used.<a href="#cite_note-Hsieh-2">[2]</a><a href="#cite_note-Quirk-3">[3]</a> Often anionic polymerization involves <a href="Living_polymerization" title="Living polymerization">living polymerizations</a>, which allows control of structure and composition.<a href="#cite_note-Hsieh-2">[2]</a><a href="#cite_note-Quirk-3">[3]</a>

<div class="mw-heading mw-heading2"><h2 id="History">History</h2></div>

As early as 1936, <a href="Karl_Ziegler" title="Karl Ziegler">Karl Ziegler</a> proposed that anionic polymerization of styrene and butadiene by consecutive addition of monomer to an alkyl lithium initiator occurred without chain transfer or termination. Twenty years later, living polymerization was demonstrated by <a href="Michael_Szwarc" title="Michael Szwarc">Michael Szwarc</a> and coworkers.<a href="#cite_note-5">[5]</a><a href="#cite_note-6">[6]</a> In one of the breakthrough events in the field of <a href="Polymer_science" title="Polymer science">polymer science</a>, Szwarc elucidated that <a href="Electron_transfer" title="Electron transfer">electron transfer</a> occurred from <a href="Radical_anion" title="Radical anion">radical anion</a> <a href="Sodium_naphthalene" title="Sodium naphthalene">sodium naphthalene</a> to <a href="Styrene" title="Styrene">styrene</a>. The results in the formation of an organosodium species, which rapidly added styrene to form a "two – ended living polymer." An important aspect of his work, Szwarc employed the <a href="Aprotic_solvent" class="mw-redirect" title="Aprotic solvent">aprotic solvent</a> <a href="Tetrahydrofuran" title="Tetrahydrofuran">tetrahydrofuran</a>. Being a <a href="Physical_chemist" class="mw-redirect" title="Physical chemist">physical chemist</a>, Szwarc elucidated the <a href="Chemical_kinetics" title="Chemical kinetics">kinetics</a> and the <a href="Thermodynamics" title="Thermodynamics">thermodynamics</a> of the process in considerable detail. At the same time, he explored the structure property relationship of the various <a href="Ion_pair" class="mw-redirect" title="Ion pair">ion pairs</a> and radical ions involved. This work provided the foundations for the synthesis of polymers with improved control over <a href="Molecular_weight" class="mw-redirect" title="Molecular weight">molecular weight</a>, molecular weight distribution, and the architecture.<a href="#cite_note-7">[7]</a>

The use of <a href="Alkali_metals" class="mw-redirect" title="Alkali metals">alkali metals</a> to initiate polymerization of 1,3-<a href="Diene" title="Diene">dienes</a> led to the discovery by <a href="Frederick_W._Stavely" title="Frederick W. Stavely">Stavely</a> and co-workers at Firestone Tire and Rubber company of cis-1,4-<a href="Polyisoprene" title="Polyisoprene">polyisoprene</a>.<a href="#cite_note-Odian-8">[8]</a> This sparked the development of commercial anionic polymerization processes that utilize alkyllithium initiators.<a href="#cite_note-Quirk-3">[3]</a>

<a href="Roderic_Quirk" title="Roderic Quirk">Roderic Quirk</a> won the 2019 <a href="Charles_Goodyear_Medal" title="Charles Goodyear Medal">Charles Goodyear Medal</a> in recognition of his contributions to anionic polymerization technology. He was introduced to the subject while working in a <a href="Phillips_Petroleum" class="mw-redirect" title="Phillips Petroleum">Phillips Petroleum</a> lab with <a href="Henry_Hsieh" title="Henry Hsieh">Henry Hsieh</a>.

<div class="mw-heading mw-heading2"><h2 id="Monomer_characteristics">Monomer characteristics</h2></div>

Two broad classes of monomers are susceptible to anionic polymerization.<a href="#cite_note-Quirk-3">[3]</a>

Vinyl monomers have the formula CH2=CHR, the most important are styrene (R = C6H5), butadiene (R = CH=CH2), and isoprene (R = C(Me)=CH2). A second major class of monomers are acrylate esters, such as <a href="Acrylonitrile" title="Acrylonitrile">acrylonitrile</a>, <a href="Methacrylate" title="Methacrylate">methacrylate</a>, <a href="Cyanoacrylate" title="Cyanoacrylate">cyanoacrylate</a>, and <a href="Acrolein" title="Acrolein">acrolein</a>. Other vinyl monomers include <a href="Vinylpyridine" title="Vinylpyridine">vinylpyridine</a>, vinyl <a href="Sulfone" title="Sulfone">sulfone</a>, vinyl <a href="Sulfoxide" title="Sulfoxide">sulfoxide</a>, <a href="Vinyl_silane" class="mw-redirect" title="Vinyl silane">vinyl silanes</a>.<a href="#cite_note-Quirk-3">[3]</a>

<div class="mw-heading mw-heading3"><h3 id="Cyclic_monomers">Cyclic monomers</h3></div>

Many cyclic compounds are susceptible to <a href="Ring-opening_polymerization" title="Ring-opening polymerization">ring-opening polymerization</a>. <a href="Epoxide" title="Epoxide">Epoxides</a>, cyclic tri<a href="Siloxane" title="Siloxane">siloxanes</a>, some lactones, <a href="Lactide" title="Lactide">lactides</a>, <a href="Cyclic_carbonate" class="mw-redirect" title="Cyclic carbonate">cyclic carbonates</a>, and <a href="Amino_acid_N-carboxyanhydride" title="Amino acid N-carboxyanhydride">amino acid N-carboxyanhydrides</a>.

In order for polymerization to occur with <a href="Vinyl_group" title="Vinyl group">vinyl</a> <a href="Monomer" title="Monomer">monomers</a>, the <a href="Substituent" title="Substituent">substituents</a> on the <a href="Double_bond" title="Double bond">double bond</a> must be able to stabilize a <a href="Negative_charge" class="mw-redirect" title="Negative charge">negative charge</a>. Stabilization occurs through <a href="Delocalization" class="mw-redirect" title="Delocalization">delocalization</a> of the negative charge. Because of the nature of the <a href="Carbanion" title="Carbanion">carbanion</a> propagating center, substituents that react with bases or nucleophiles either must not be present or be protected.<a href="#cite_note-Quirk-3">[3]</a>

<div class="mw-heading mw-heading2"><h2 id="Initiation">Initiation</h2></div>

Initiators are selected based on the reactivity of the monomers. Highly electrophilic monomers such as cyanoacrylates require only weakly nucleophilic initiators, such as amines, phosphines, or even halides. Less reactive monomers such as styrene require powerful nucleophiles such as <a href="Butyl_lithium" class="mw-redirect" title="Butyl lithium">butyl lithium</a>. Reactions of intermediate strength are used for monomers of intermediate reactivity such as <a href="Vinylpyridine" title="Vinylpyridine">vinylpyridine</a>.<a href="#cite_note-Quirk-3">[3]</a>

The solvents used in anionic addition polymerizations are determined by the reactivity of both the initiator and nature of the propagating chain end. Anionic species with low reactivity, such as <a href="Heterocyclic" class="mw-redirect" title="Heterocyclic">heterocyclic</a> monomers, can use a wide range of solvents.<a href="#cite_note-Quirk-3">[3]</a>

<div class="mw-heading mw-heading3"><h3 id="Initiation_by_electron_transfer">Initiation by electron transfer</h3></div>

Initiation of styrene polymerization with <a href="Sodium_naphthalene" title="Sodium naphthalene">sodium naphthalene</a> proceeds by <a href="Electron_transfer" title="Electron transfer">electron transfer</a> from the <a href="Naphthalene" title="Naphthalene">naphthalene</a> <a href="Radical_anion" title="Radical anion">radical anion</a> to the monomer. The resulting radical dimerizes to give a disodium compound, which then functions as the initiator. Polar solvents are necessary for this type of initiation both for stability of the anion-radical and to solvate the cation species formed.<a href="#cite_note-Odian-8">[8]</a> The anion-radical can then transfer an electron to the monomer.

Initiation can also involve the transfer of an electron from the alkali metal to the monomer to form an anion-radical. Initiation occurs on the surface of the metal, with the reversible transfer of an electron to the adsorbed monomer.<a href="#cite_note-Quirk-3">[3]</a>

<div class="mw-heading mw-heading3"><h3 id="Initiation_by_strong_anions">Initiation by strong anions</h3></div>

Nucleophilic initiators include covalent or ionic metal <a href="Amide" title="Amide">amides</a>, <a href="Alkoxide" title="Alkoxide">alkoxides</a>, <a href="Hydroxide" title="Hydroxide">hydroxides</a>, <a href="Cyanide" title="Cyanide">cyanides</a>, <a href="Phosphine" title="Phosphine">phosphines</a>, <a href="Amine" title="Amine">amines</a> and organometallic compounds (alkyllithium compounds and <a href="Grignard_reagents" class="mw-redirect" title="Grignard reagents">Grignard reagents</a>). The initiation process involves the addition of a neutral (B:) or negative (:B−) <a href="Nucleophile" title="Nucleophile">nucleophile</a> to the monomer.<a href="#cite_note-Odian-8">[8]</a>

The most commercially useful of these initiators has been the <a href="Alkyllithium" class="mw-redirect" title="Alkyllithium">alkyllithium</a> initiators. They are primarily used for the polymerization of styrenes and dienes.<a href="#cite_note-Quirk-3">[3]</a>

Monomers activated by strong electronegative groups may be initiated even by weak anionic or neutral nucleophiles (i.e. amines, phosphines). Most prominent example is the curing of cyanoacrylate, which constitutes the basis for <a href="Superglue" class="mw-redirect" title="Superglue">superglue</a>. Here, only traces of basic impurities are sufficient to induce an anionic addition polymerization or zwitterionic addition polymerization, respectively.<a href="#cite_note-9">[9]</a>

<div class="mw-heading mw-heading2"><h2 id="Propagation">Propagation</h2></div>

Propagation in anionic addition polymerization results in the complete consumption of monomer. This stage is often fast, even at low temperatures.<a href="#cite_note-Hsieh-2">[2]</a>

<div class="mw-heading mw-heading2"><h2 id="Living_anionic_polymerization">Living anionic polymerization</h2></div>

Living anionic polymerization is a <a href="Living_polymerization" title="Living polymerization">living polymerization</a> technique involving an <a href="Anionic" class="mw-redirect" title="Anionic">anionic</a> propagating species.

Living anionic polymerization was demonstrated by Szwarc and co workers in 1956. Their initial work was based on the polymerization of styrene and dienes.

One of the remarkable features of living anionic polymerization is that the mechanism involves no formal termination step. In the absence of impurities, the carbanion would still be active and capable of adding another monomer. The chains will remain active indefinitely unless there is inadvertent or deliberate termination or chain transfer. This gave rise to two important consequences:

<ol><li>The <a href="Number_average_molecular_weight" class="mw-redirect" title="Number average molecular weight">number average molecular weight</a>, Mn, of the polymer resulting from such a system could be calculated by the amount of consumed monomer and the initiator used for the polymerization, as the degree of polymerization would be the ratio of the moles of the monomer consumed to the moles of the initiator added.

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<annotation encoding="application/x-tex">{\displaystyle M_{n}=M_{o}{\frac {[{\mbox{M}}]_{o}}{[{\mbox{I}}]}}}</annotation>

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</math><img src="./86220a1bcee2334650c55dd7e3525f348836042b.svg" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -2.671ex; width:15.145ex; height:6.509ex;" alt="{\displaystyle M_{n}=M_{o}{\frac {[{\mbox{M}}]_{o}}{[{\mbox{I}}]}}}" loading="lazy">, where Mo = formula weight of the repeating unit, [M]o = initial concentration of the monomer, and [I] = concentration of the initiator.</dd></dl></li>

<li>All the chains are initiated at roughly the same time. The final result is that the polymer synthesis can be done in a much more controlled manner in terms of the molecular weight and molecular weight distribution (<a href="Poisson_distribution" title="Poisson distribution">Poisson distribution</a>).</li></ol>

The following experimental criteria have been proposed as a tool for identifying a system as living polymerization system.

<ul><li>Polymerization until the monomer is completely consumed and until further monomer is added.</li>

<li>Constant number of active centers or propagating species.</li>

<li><a href="Poisson_distribution" title="Poisson distribution">Poisson distribution</a> of molecular weight</li>

<li>Chain end functionalization can be carried out quantitatively.</li></ul>

However, in practice, even in the absence of terminating agents, the concentration of the living anions will reduce with time due to a decay mechanism termed as spontaneous termination.<a href="#cite_note-Odian-8">[8]</a>

<div class="mw-heading mw-heading2"><h2 id="Consequences_of_living_polymerization">Consequences of living polymerization</h2></div>

<div class="mw-heading mw-heading3"><h3 id="Block_copolymers">Block copolymers</h3></div>

Synthesis of block copolymers is one of the most important applications of living polymerization as it offers the best control over structure. The <a href="Nucleophilicity" class="mw-redirect" title="Nucleophilicity">nucleophilicity</a> of the resulting carbanion will govern the order of monomer addition, as the monomer forming the less nucleophilic propagating species may inhibit the addition of the more nucleophilic monomer onto the chain. An extension of the above concept is the formation of triblock copolymers where each step of such a sequence aims to prepare a block segment with predictable, known molecular weight and narrow molecular weight distribution without chain termination or transfer.<a href="#cite_note-10">[10]</a>

Sequential monomer addition is the dominant method, also this simple approach suffers some limitations.

Moreover, this strategy, enables synthesis of linear block copolymer structures that are not accessible via sequential monomer addition. For common A-b-B structures, sequential block copolymerization gives access to well defined

block copolymers only if the crossover reaction rate constant is significantly higher than the rate constant of the homopolymerization

of the second monomer, i.e., kAA >> kBB.<a href="#cite_note-11">[11]</a>

<div class="mw-heading mw-heading3"><h3 id="End-group_functionalization/termination">End-group functionalization/termination</h3></div>

One of the remarkable features of living anionic polymerization is the absence of a formal termination step. In the absence of impurities, the carbanion would remain active, awaiting the addition of new monomer. Termination can occur through unintentional quenching by impurities, often present in trace amounts. Typical impurities include <a href="Oxygen" title="Oxygen">oxygen</a>, <a href="Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a>, or <a href="Water" title="Water">water</a>. Termination intentionally allows the introduction of tailored end groups.

Living anionic polymerization allow the incorporation of functional <a href="End-group" class="mw-redirect" title="End-group">end-groups</a>, usually added to quench polymerization. End-groups that have been used in the functionalization of α-haloalkanes include <a href="Hydroxide" title="Hydroxide">hydroxide</a>, -NH2, -OH, -SH, -CHO,-COCH3, -COOH, and epoxides.

An alternative approach for functionalizing end-groups is to begin polymerization with a functional anionic initiator.<a href="#cite_note-HongK-12">[12]</a> In this case, the functional groups are protected since the ends of the anionic polymer chain is a strong base. This method leads to polymers with controlled molecular weights and narrow molecular weight distributions.<a href="#cite_note-13">[13]</a>

<div class="mw-heading mw-heading2"><h2 id="Additional_reading">Additional reading</h2></div>

<ul><li>Cowie, J.; Arrighi, V. Polymers: Chemistry and Physics of Modern Materials; CRC Press: Boca Raton, FL, 2008.</li>

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</style><cite id="CITEREFHadjichristidis,_N.Iatrou,_H.Pitsikalis,_P.Mays,_J.2006" class="citation journal cs1">Hadjichristidis, N.; Iatrou, H.; Pitsikalis, P.; Mays, J. (2006). "Macromolecular architectures by living and controlled/living polymerizations". Prog. Polym. Sci. 31 (12): 1068–1132. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.progpolymsci.2006.07.002">10.1016/j.progpolymsci.2006.07.002</a>.</cite></li>

<li><cite id="CITEREFEfstratiadis,_V.Tselikas,_Y.Hadjichristidis,_N.Li,_J.1994" class="citation journal cs1">Efstratiadis, V.; Tselikas, Y.; Hadjichristidis, N.; Li, J.; Yunan, W.; Mays, J. (1994). "Synthesis and characterization of poly(methyl methacrylate) star polymers". Polym Int. 4 (2): 171–179. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fpi.1994.210330208">10.1002/pi.1994.210330208</a>.</cite></li>

<li><cite id="CITEREFRempp,_P.Franta,_E.Herz,_J.1998" class="citation book cs1">Rempp, P.; Franta, E.; Herz, J. (1998). "Macromolecular Engineering by Anionic Methods". Polysiloxane Copolymers/Anionic Polymerization. Advances in Polymer Science. Vol. 4. pp. 145–173. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2FBFb0025276">10.1007/BFb0025276</a>. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>978-3-540-18506-2</bdi>. <a href="S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:92176703">92176703</a>.</cite></li>

<li><cite id="CITEREFBellasRehahn2007" class="citation journal cs1">Bellas, Vasilios; Rehahn, Matthias (2 July 2007). "Universal Methodology for Block Copolymer Synthesis". Macromolecular Rapid Communications. 28 (13): 1415–1421. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fmarc.200700127">10.1002/marc.200700127</a>. <a href="S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:96556942">96556942</a>.</cite></li>

<li><cite id="CITEREFNikos_HadjichristidisAkira_Hirao2015" class="citation book cs1">Nikos Hadjichristidis; Akira Hirao, eds. (2015). Anionic Polymerization Principles, Practice, Strength, Consequences and Applications. Springer. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>978-4-431-54186-8</bdi>.</cite></li></ul>

<div class="mw-heading mw-heading2"><h2 id="References">References</h2></div>

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<li id="cite_note-Gold_Book_"anionic_polymerization"-1"><a href="#cite_ref-Gold_Book_"anionic_polymerization"_1-0">^</a> <cite id="Gold_Book_A00361" class="citation web cs1"><a rel="nofollow" class="external text" href="https://goldbook.iupac.org/terms/view/A00361">"anionic polymerization"</a>. Gold Book. IUPAC. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1351%2Fgoldbook.A00361">10.1351/goldbook.A00361</a>. Retrieved 1 April 2024.</cite>

</li>

<li id="cite_note-Hsieh-2">^ <a href="#cite_ref-Hsieh_2-0">a</a> <a href="#cite_ref-Hsieh_2-1">b</a> <a href="#cite_ref-Hsieh_2-2">c</a> Hsieh, H.;Quirk, R. Anionic Polymerization: Principles and practical applications; Marcel Dekker, Inc.: New York, 1996.

</li>

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