Skip to main content
Fachgebiete
Automobil + Motoren Bauwesen + Immobilien Business IT + Informatik Elektrotechnik + Elektronik Energie + Nachhaltigkeit Finance + Banking Management + Führung Marketing + Vertrieb Maschinenbau + Werkstoffe Versicherung + Risiko
DE
EN
Themenseiten
Organisationspsychologie Projektmanagement Marketing Smart Manufacturing
Bücher
Zeitschriften
Weitere Formate
Podcasts Webinare Technik Webinare Wirtschaft Kongresse Veranstaltungskalender Awards
Jetzt Einzelzugang starten
Zugang für Unternehmen
Referenzkunden
MTZ-Fachkongress

Antriebe und Energiesysteme von morgen


Austausch von Automobil- und Energiewirtschaft

Am 14./15. Mai geht es in Chemnitz um die Mobilitätswende durch Elektro- und Wasserstofffahrzeuge.
Erweiterte Suche
Anmelden
nach oben
Colloid and Polymer Science
Erschienen in: Colloid and Polymer Science 9/2013

01.09.2013 | Original Contribution

Controlled ring-opening polymerization of cyclic esters with phosphoric acid as catalysts

verfasst von: Xi Zhou, Liangzhi Hong

Erschienen in: Colloid and Polymer Science | Ausgabe 9/2013

Einloggen

Aktivieren Sie unsere intelligente Suche, um passende Fachinhalte oder Patente zu finden.

search-config
loading …

Abstract

(R)-(−)-1,1′-Binaphthyl-2,2′-diyl hydrogen phosphate (BPA) has been demonstrated as an efficient organocatalyst for controlled ring-opening homopolymerization of ε-caprolactone (ε-CL) and copolymerization of ε-CL with glycolide and lactide. High molar mass PCL with narrow molar mass distribution has also been synthesized from the bulk ring-opening polymerization (ROP) of ε-CL with BPA as catalysts; the highest molar mass of PCL is 4.35 × 104 g/mol with polydispersity index of 1.20. The successful synthesis of high molar mass PCL is attributed to the bifunctional activation mechanism for the ROP of ε-CL catalyzed by BPA. More interestingly, ppm level of BPA is sufficient to catalyze controlled ROP of ε-CL.
Vorheriger Artikel Microfluidic-directed assembly of uniform fluorescent supraballs from CdTe nanocrystals-loaded acrylosilane microemulsion
Nächster Artikel Anomalous small-angle x-ray scattering from mesoporous noble metal catalysts

Sie haben noch keine Lizenz? Dann Informieren Sie sich jetzt über unsere Produkte:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

  • über 102.000 Bücher
  • über 537 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Finance + Banking
  • Management + Führung
  • Marketing + Vertrieb
  • Maschinenbau + Werkstoffe
  • Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

Jetzt informieren

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

  • über 67.000 Bücher
  • über 390 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Maschinenbau + Werkstoffe




 

Jetzt Wissensvorsprung sichern!

Jetzt informieren
Literatur
1.
Hayashi T (1994) Biodegradable polymers for biomedical uses. Prog Polym Sci 19:663–702CrossRef
2.
Albertsson AC, Varma IK (2003) Recent developments in ring opening polymerization of lactones for biomedical applications. Biomacromolecules 4:1466–1486CrossRef
3.
Woodruff MA, Hutmacher DW (2010) The return of a forgotten polymer-Polycaprolactone in the 21st century. Prog Polym Sci 35:1217–1256CrossRef
4.
Zhao W, Wang Y, Liu X, Chen X, Cui D, Chen EYX (2012) Protic compound mediated living cross-chain-transfer polymerization of rac-lactide: synthesis of isotactic (crystalline)-heterotactic (amorphous) stereomultiblock polylactide. Chem Commun 48:6375–6377CrossRef
5.
Mecerreyes D, Jerome R, Dubois P (1999) Novel macromolecular architectures based on aliphatic polyesters: relevance of the "coordination-insertion" ring-opening polymerization. Adv Polym Sci 147:1–59CrossRef
6.
Majerska K, Duda A, Penczek S (2000) Kinetics and mechanism of cyclic esters polymerisation initiated with tin(II) octoate, 4—Influence of proton trapping agents on the kinetics of epsilon-caprolactone and L, L-dilactide polymerisation. Macromol Rapid Commun 21:1327–1332CrossRef
7.
Labet M, Thielemans W (2009) Synthesis of polycaprolactone: a review. Chem Soc Rev 38:3484–3504CrossRef
8.
Wang Y, Zhang LF, Wang P, Shen LJ (2010) Ring-opening polymerization of l-lactide with rare earth aryloxides substituted by various alkyl groups. Chin J Polym Sci 28:509–515CrossRef
9.
Sun JQ, Pan ZD, Yang SL (1998) Ring-opening polymerization of epsilon-caprolactone by lanthanocene catalysis. Chin J Polym Sci 16:297–303
10.
Save M, Soum A (2002) Controlled ring-opening polymerization of Lactones and lactide initiated by lanthanum isopropoxide, 2—mechanistic studies. Macromol Chem Phys 203:2591–2603CrossRef
11.
Jerome C, Lecomte P (2008) Recent advances in the synthesis of aliphatic polyesters by ring-opening polymerization. Adv Drug Deliv Rev 60:1056–1076CrossRef
12.
Kiesewetter MK, Shin EJ, Hedrick JL, Waymouth RM (2010) Organocatalysis: opportunities and challenges for polymer synthesis. Macromolecules 43:2093–2107CrossRef
13.
Kamber NE, Jeong W, Waymouth RM, Pratt RC, Lohmeijer BGG, Hedrick JL (2007) Organocatalytic ring-opening polymerization. Chem Rev 107:5813–5840CrossRef
14.
Nederberg F, Connor EF, Moller M, Glauser T, Hedrick JL (2001) New paradigms for organic catalysts: The first organocatalytic living polymerization. Angew Chem Int Ed 40:2712–2715CrossRef
15.
Connor EF, Nyce GW, Myers M, Mock A, Hedrick JL (2002) First example of N-heterocyclic carbenes as catalysts for living polymerization: organocatalytic ring-opening polymerization of cyclic esters. J Am Chem Soc 124:914–915CrossRef
16.
Myers M, Connor EF, Glauser T, Mock A, Nyce G, Hedrick JL (2002) Phosphines: nucleophilic organic catalysts for the controlled ring-opening polymerization of lactides. J Polym Sci Part A: Polym Chem 40:844–851CrossRef
17.
Dove AP, Pratt RC, Lohmeijer BGG, Waymouth RM, Hedrick JL (2005) Thiourea-based bifunctional organocatalysis: supramolecular recognition for living polymerization. J Am Chem Soc 127:13798–13799CrossRef
18.
Gazeau-Bureau S, Delcroix D, Martin-Vaca B, Bonrissou D, Navarro C, Magnet S (2008) Organo-catalyzed ROP of epsilon-caprolactone: methanesulfonic acid competes with trifluoromethanesulfonic acid. Macromolecules 41:3782–3784CrossRef
19.
Shibasaki Y, Sanada H, Yokoi M, Sanda F, Endo T (2000) Activated monomer cationic polymerization of lactones and the application to well-defined block copolymer synthesis with seven-membered cyclic carbonate. Macromolecules 33:4316–4320CrossRef
20.
Persson PV, Schroder J, Wickholm K, Hedenstrom E, Iversen T (2004) Selective organocatalytic ring-opening polymerization: a versatile route to carbohydrate-functionalized poly(is an element of-caprolactones). Macromolecules 37:5889–5893CrossRef
21.
Casas J, Persson PV, Iversen T, Cordova A (2004) Direct organocatalytic ring-opening polymerizations of lactones. Adv Synth Catal 346:1087–1089CrossRef
22.
Kakuchi R, Tsuji Y, Chiba K, Fuchise K, Sakai R, Satoh T, Kakuchi T (2010) Controlled/living ring-opening polymerization of delta-valerolactone using triflylimide as an efficient cationic organocatalyst. Macromolecules 43:7090–7094CrossRef
23.
Sanda F, Sanada H, Shibasaki Y, Endo T (2002) Star polymer synthesis from epsilon-caprolactone utilizing polyol/protonic acid initiator. Macromolecules 35:680–683CrossRef
24.
Lou XD, Detrembleur C, Jerome R (2002) Living cationic polymerization of delta-valerolactone and synthesis of high molecular weight homopolymer and asymmetric telechelic and block copolymer. Macromolecules 35:1190–1195CrossRef
25.
Basko M, Kubisa P (2006) Cationic copolymerization of epsilon-caprolactone and L, L-lactide by an activated monomer mechanism. J Polym Sci A Polym Chem 44:7071–7081CrossRef
26.
Kim MS, Seo KS, Khang G, Lee HB (2005) Ring-opening polymerization of epsilon-caprolactone by poly(ethylene glycol) by an activated monomer mechanism. Macromol Rapid Commun 26:643–648CrossRef
27.
Basko M, Kubisa P (2007) Polyester oligodiols by cationic AM copolymerization of L, L-lactide and epsilon-caprolactone initiated by diols. J Polym Sci A Polym Chem 45:3090–3097CrossRef
28.
Athanasiou KA, Niederauer GG, Agrawal CM (1996) Sterilization, toxicity, biocompatibility, and clinical applications of polylactic acid/polyglycolic acid copolymers. Biomaterials 17:93–102CrossRef
29.
Gupta B, Revagade N, Hilborn J (2007) Poly(lactic acid) fiber: an overview. Prog Polym Sci 32:455–482CrossRef
30.
Jain RA (2000) The manufacturing techniques of various drug loaded biodegradable poly(lactide-co-glycolide) (PLGA) devices. Biomaterials 21:2475–2490CrossRef
31.
Ratner BD, Hoffman AS, Schoen FJ, Lemons JE (2004) Biomaterials science: an introduction to materials in medicine, 2nd edn. Elsevier Academic Press, Singapore
32.
Dechy-Cabaret O, Martin-Vaca B, Bourissou D (2004) Controlled ring-opening polymerization of lactide and glycolide. Chem Rev 104:6147–6176CrossRef
33.
Bourissou D, Martin-Vaca B, Dumitrescu A, Graullier M, Lacombe F (2005) Controlled cationic polymerization of lactide. Macromolecules 38:9993–9998CrossRef
34.
Basko M, Kubisa P (2008) Mechanism of propagation in the cationic polymerization of L, L-Lactide. J Polym Sci A Polym Chem 46:7919–7923CrossRef
35.
Basko M, Kubisa P (2010) Cationic polymerization of L, L-Lactide. J Polym Sci A Polym Chem 48:2650–2658CrossRef
36.
Dechy-Cabaret O, Martin-Vaca B, Bourissou D (2004) Controlled ring-opening polymerization of lactide and glycolide. Chem Rev 104:6147–6176CrossRef
37.
Makiguchi K, Satoh T, Kakuchi T (2011) Diphenyl phosphate as an efficient cationic organocatalyst for controlled/living ring-opening polymerization of delta-valerolactone and epsilon-caprolactone. Macromolecules 44:1999–2005CrossRef
38.
Delcroix D, Couffin A, Susperregui N, Navarro C, Maron L, Martin-Vaca B, Bourissou D (2011) Phosphoric and phosphoramidic acids as bifunctional catalysts for the ring-opening polymerization of epsilon-caprolactone: a combined experimental and theoretical study. Polym Chem 2:2249–2256CrossRef
39.
Chen C, Xu R, Li B (2012) Controlled/living ring-opening polymerization of epsiv-caprolactone catalyzed by phosphoric acid. Sci China Chem 55:1257CrossRef
40.
Pratt RC, Lohmeijer BGG, Long DA, Waymouth RM, Hedrick JL (2006) Triazabicyclodecene: a simple bifunctional organocatalyst for acyl transfer and ring-opening polymerization of cyclic esters. J Am Chem Soc 128:4556–4557CrossRef
41.
Zhou SB, Xu JG, Yang H, Deng XM (2004) Synthesis and characterization of biodegradable poly(epsilon-caprolactone)-polyglycolide-poly(ethylene glycol) monomethyl ether random copolymer. Macromol Mater Eng 289:576–580CrossRef
42.
Yang H, Xu J, Pispas S, Zhang G (2012) Hybrid copolymerization of epsilon-caprolactone and methyl methacrylate. Macromolecules 45:3312–3317CrossRef
Metadaten
Titel
Controlled ring-opening polymerization of cyclic esters with phosphoric acid as catalysts
verfasst von
Xi Zhou
Liangzhi Hong
Publikationsdatum
01.09.2013
Verlag
Springer Berlin Heidelberg
Erschienen in
Colloid and Polymer Science / Ausgabe 9/2013
Print ISSN: 0303-402X
Elektronische ISSN: 1435-1536
DOI
https://doi.org/10.1007/s00396-013-2950-9

Weitere Artikel der Ausgabe 9/2013

Colloid and Polymer Science 9/2013 Zur Ausgabe

Original Contribution

Factors affecting the TMPTA radical polymerization photoinitiated by phenyltrialkylborates paired with tri-cationic hemicyanine dye. Kinetic studies

Short Communication

Synthesis of a main-chain liquid crystalline azo-polymer via “click” chemistry

Original Contribution

Influence of the third monomer on lauryl methacrylate–methyl methacrylate emulsion terpolymerization

Original Contribution

Alternating copolymerization of carbon dioxide and cyclohexene oxide catalyzed by salen CoIII(acetate) complexes

Original Contribution

Electrochemical property of graphene oxide/polyaniline composite prepared by in situ interfacial polymerization

Original Contribution

Sulfonated graphene oxide: the new and effective material for synthesis of polystyrene-based nanocomposites

Premium Partner

    Marktübersichten

    Die im Laufe eines Jahres in der „adhäsion“ veröffentlichten Marktübersichten helfen Anwendern verschiedenster Branchen, sich einen gezielten Überblick über Lieferantenangebote zu verschaffen. 

    Zur Marktübersicht
    Bildnachweise