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Condensation polymer

From Wikipedia, the free encyclopedia
(Redirected fromPolycondensation)
Polymer produced via a condensation reaction
Polymer science
Polyacetylene
Polyethylene terephthalate (PET) is a common condensation polymer.

Inpolymer chemistry,condensation polymers are any kind ofpolymers whose process ofpolymerization involves acondensation reaction (i.e. a small molecule, such aswater ormethanol, is produced as a byproduct). Naturalproteins as well as some common plastics such asnylon andPETE are formed in this way. Condensation polymers are formed by polycondensation, when the polymer is formed by condensation reactions between species of alldegrees of polymerization, or by condensativechain polymerization, when the polymer is formed by sequential addition of monomers to anactive site in achain reaction. The main alternative forms of polymerization are chain polymerization andpolyaddition, both of which giveaddition polymers.

IUPAC definition

Polycondensation:a polymerization in which the growth of polymer chains proceeds by condensation reactions between molecules of all degrees of polymerization.Notes:

  1. The growth steps are expressed by:
    Px + Py → Px+y + L (x,y = 1, 2, …)
    wherePx andPy denote chains of degrees of polymerizationx andy, respectively, and L a low-molar-mass by-product.
  2. The earlier term 'polycondensation' was synonymous with 'condensation polymerization'. The current definitions of polycondensation and condensative chain polymerization were both embraced by the earlier term 'polycondensation'.[1]

Condensation polymerization is a form ofstep-growth polymerization. Linear polymers are produced frombifunctional monomers, i.e. compounds with two reactiveend-groups. Common condensation polymers includepolyesters,polyamides such asnylon,polyacetals, andproteins.[2][3]

Polyamides

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One important class of condensation polymers arepolyamides.[4] They arise from the reaction ofcarboxylic acid and an amine. Examples includenylons andproteins. When prepared from amino-carboxylic acids, e.g. amino acids, the stoichiometry of the polymerization includes co-formation of water:

n H2N-X-CO2H → [HN-X-C(O)]n + (n-1) H2O

When prepared fromdiamines anddicarboxylic acids, e.g. the production ofnylon 66, the polymerization produces two molecules of water per repeat unit:

n H2N-X-NH2 + n HO2C-Y-CO2H → [HN-X-NHC(O)-Y-C(O)]n + (2n-1) H2O
General chemical structure of one type of condensation polymer

Polyesters

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Another important class of condensation polymers arepolyesters.[5] They arise from the reaction of acarboxylic acid and an alcohol. An example ispolyethyleneterephthalate, the common plastic PET (recycling #1 in the USA):

n HO-X-OH + n HO2C-Y-CO2H → [O-X-O2C-Y-C(O)]n + (2n-1) H2O
Structure ofpoly-(R)-3-hydroxybutyrate (P3HB), a naturally-occurring polymer.

Safety and environmental considerations

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Condensation polymers tend to be more biodegradable thanaddition polymers. The peptide or ester bonds between monomers can be hydrolysed, especially in the presence of catalysts or bacterialenzymes.[6]

See also

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References

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  1. ^Jenkins, A. D.; Kratochvíl, P.; Stepto, R. F. T.; Suter, U. W. (1996-01-01)."Glossary of basic terms in polymer science (IUPAC Recommendations 1996)".Pure and Applied Chemistry.68 (12):2287–2311.doi:10.1351/pac199668122287.ISSN 0033-4545.S2CID 98774337.
  2. ^Introduction to Polymers 1987 R.J. Young Chapman & HallISBN 0-412-22170-5
  3. ^D. Margerison; G. C. East; J. E. Spice (1967).An Introduction to Polymer Chemistry. Pergamon Press.ISBN 978-0-08-011891-8.
  4. ^B. Herzog; M. I. Kohan; S. A. Mestemacher; R. U. Pagilagan; K. Redmond (2013). "Polyamides".Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH.doi:10.1002/14356007.a21_179.pub3.ISBN 978-3-527-30673-2.S2CID 241272519.
  5. ^Horst Köpnick; Manfred Schmidt; Wilhelm Brügging; Jörn Rüter; Walter Kaminsky (2002). "Polyesters".Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH.doi:10.1002/14356007.a21_227.ISBN 3-527-30673-0.
  6. ^Wei, Ren; Zimmermann, Wolfgang (November 2017)."Microbial enzymes for the recycling of recalcitrant petroleum-based plastics: how far are we?".Microbial Biotechnology.10 (6):1308–1322.doi:10.1111/1751-7915.12710.PMC 5658625.PMID 28371373.

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