Skip to main content
Erschienen in: Polymer Bulletin 1/2018

28.04.2017 | Original Paper

Curable precursors derived from chemical recycling of poly(ethylene terephthalate) and polylactic acid and physical properties of their thermosetting (co)polyesters

verfasst von: O. Torpanyacharn, P. Sukpuang, A. Petchsuk, P. Opaprakasit, M. Opaprakasit

Erschienen in: Polymer Bulletin | Ausgabe 1/2018

Einloggen

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

search-config
loading …

Abstract

Curable precursors for production of thermosetting (co)polyesters are developed based on poly(butylene adipate) (PBA), poly(ethylene terephthalate), and poly(lactic acid) (PLA). The precursors are prepared from methacrylation of their hydroxyl-terminated oligomers. These include commercial HO-capped PBA prepolymer (HO-PBA), and bis-2-hydroxyethyl terephthalate (BHET) and glycolized PLA (GPLA), which are obtained from glycolysis reactions of their post-consumer products and original resin. The optimal conditions for methacrylation of each prepolymer, i.e., molar ratios of prepolymer to methacrylic anhydride (MAAH), temperature and time, are examined. The most efficient conditions are 1:4/120 °C/3 h (HO-PBA), 1:2.5/120 °C/2 h (BHET), and 1:4/140 °C/3 h (GPLA), respectively. These conditions are justified, where the highest degree of substitution and double bond content are obtained without self-curing side reaction. The resulting methacrylated precursors from HO-PBA and BHET are isothermally cured faster than those of GPLA. Thermosetting copolyesters developed from binary mixtures of the precursors possess tunable thermal stability, and physical and mechanical properties. The degradable copolyesters can be applied in various applications, especially in packaging and agricultural fields.

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!

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!

Literatur
1.
Zurück zum Zitat Sukpuang P, Petchsuk A, Opaprakasit P, Opaprakasit M (2009) Synthesis and characterizations of poly(lactic acid-co-ethylene terephthalate) from glycolysed products. In: Pure and applied chemistry international conference (PACCON), Phitsanulok, Thailand, pp 582–585 Sukpuang P, Petchsuk A, Opaprakasit P, Opaprakasit M (2009) Synthesis and characterizations of poly(lactic acid-co-ethylene terephthalate) from glycolysed products. In: Pure and applied chemistry international conference (PACCON), Phitsanulok, Thailand, pp 582–585
2.
Zurück zum Zitat Tounthai J, Petchsuk A, Opaprakasit P, Opaprakasit M (2013) Curable polyester precursors from polylactic acid glycolyzed products. Polym Bull 70:2223–2238CrossRef Tounthai J, Petchsuk A, Opaprakasit P, Opaprakasit M (2013) Curable polyester precursors from polylactic acid glycolyzed products. Polym Bull 70:2223–2238CrossRef
3.
Zurück zum Zitat Sukpuang P, Petchsuk A, Opaprakasit P, Opaprakasit M (2014) Toughness enhancement of polylactic acid by employing glycolyzed polylactic acid-cured epoxidized natural rubber. Adv Mater Res 1025–1026:580–584CrossRef Sukpuang P, Petchsuk A, Opaprakasit P, Opaprakasit M (2014) Toughness enhancement of polylactic acid by employing glycolyzed polylactic acid-cured epoxidized natural rubber. Adv Mater Res 1025–1026:580–584CrossRef
4.
Zurück zum Zitat Sukpuang P, Opaprakasit M, Petchsuk A, Tangboriboonrat P, Sojikul P, Opaprakasit P (2016) Polylactic acid glycolysate as a cross-linker for epoxidized natural rubber: effect of cross-linker molecular weight. J Elastom Plast 48(2):105–121CrossRef Sukpuang P, Opaprakasit M, Petchsuk A, Tangboriboonrat P, Sojikul P, Opaprakasit P (2016) Polylactic acid glycolysate as a cross-linker for epoxidized natural rubber: effect of cross-linker molecular weight. J Elastom Plast 48(2):105–121CrossRef
5.
Zurück zum Zitat Chen C, Lo Y, Mao C, Liao W (2001) Studies of glycolysis of poly(ethylene terephthalate) recycled from postconsumer soft-drink bottles. I. Influences of glycolysis conditions. J Appl Polym Sci 80:943–948CrossRef Chen C, Lo Y, Mao C, Liao W (2001) Studies of glycolysis of poly(ethylene terephthalate) recycled from postconsumer soft-drink bottles. I. Influences of glycolysis conditions. J Appl Polym Sci 80:943–948CrossRef
6.
Zurück zum Zitat Chen CH, Chen CY, Lo YW, Mao CF, Liao WT (2001) Studies of glycolysis of poly(ethylene terephthalate) recycled from postconsumer soft-drink bottles. II. Factorial experimental design. J Appl Polym Sci 80(7):956–962CrossRef Chen CH, Chen CY, Lo YW, Mao CF, Liao WT (2001) Studies of glycolysis of poly(ethylene terephthalate) recycled from postconsumer soft-drink bottles. II. Factorial experimental design. J Appl Polym Sci 80(7):956–962CrossRef
7.
Zurück zum Zitat Xi G, Lu M, Sun C (2005) Study on depolymerization of waste polyethylene terephthalate into monomer of bis(2-hydroxyethyl terephthalate). Polym Degrad Stab 87(1):117–120CrossRef Xi G, Lu M, Sun C (2005) Study on depolymerization of waste polyethylene terephthalate into monomer of bis(2-hydroxyethyl terephthalate). Polym Degrad Stab 87(1):117–120CrossRef
8.
Zurück zum Zitat Helminen AO, Korhonen H, Seppala JV (2003) Crosslinked poly(ester anhydride)s based on poly(ε-caprolactone) and polylactide oligomers. J Polym Sci A Polym Chem 41(23):3788–3797CrossRef Helminen AO, Korhonen H, Seppala JV (2003) Crosslinked poly(ester anhydride)s based on poly(ε-caprolactone) and polylactide oligomers. J Polym Sci A Polym Chem 41(23):3788–3797CrossRef
9.
Zurück zum Zitat Ho SM, Young AM (2006) Synthesis, polymerisation and degradation of poly(lactide-co-propylene glycol) dimethacrylate adhesives. Eur Polym J 42(8):1775–1785CrossRef Ho SM, Young AM (2006) Synthesis, polymerisation and degradation of poly(lactide-co-propylene glycol) dimethacrylate adhesives. Eur Polym J 42(8):1775–1785CrossRef
10.
Zurück zum Zitat Helminen A, Korhonen H, Seppala JV (2001) Biodegradable crosslinked polymers based on triethoxysilane terminated polylactide oligomers. Polymer 42(8):3345–3353CrossRef Helminen A, Korhonen H, Seppala JV (2001) Biodegradable crosslinked polymers based on triethoxysilane terminated polylactide oligomers. Polymer 42(8):3345–3353CrossRef
11.
Zurück zum Zitat Helminen AO, Korhonen H, Seppala JV (2002) Structure modification and crosslinking of methacrylated polylactide oligomers. J Appl Polym Sci 86(14):3616–3624CrossRef Helminen AO, Korhonen H, Seppala JV (2002) Structure modification and crosslinking of methacrylated polylactide oligomers. J Appl Polym Sci 86(14):3616–3624CrossRef
12.
Zurück zum Zitat Helminen AO, Korhonen H, Seppala JV (2002) Cross-linked poly(ε-caprolactone/d,l-lactide) copolymers with elastic properties. Macromol Chem Phys 203(18):2630–2639CrossRef Helminen AO, Korhonen H, Seppala JV (2002) Cross-linked poly(ε-caprolactone/d,l-lactide) copolymers with elastic properties. Macromol Chem Phys 203(18):2630–2639CrossRef
13.
Zurück zum Zitat Storey RF, Warren SC, Allison CJ, Puckett AD (1997) Methacrylate-endcapped poly(d,l-lactide-co-trimethylene carbonate) oligomers. Network formation by thermal free-radical curing. Polymer 38(26):6295–6301CrossRef Storey RF, Warren SC, Allison CJ, Puckett AD (1997) Methacrylate-endcapped poly(d,l-lactide-co-trimethylene carbonate) oligomers. Network formation by thermal free-radical curing. Polymer 38(26):6295–6301CrossRef
14.
Zurück zum Zitat Bencherif SA, Srinivasan A, Horkay F, Hollinger JO, Matyjaszewski K, Washburn NR (2008) Influence of the degree of methacrylation on hyaluronic acid hydrogels properties. Biomaterials 29(12):1739–1749CrossRef Bencherif SA, Srinivasan A, Horkay F, Hollinger JO, Matyjaszewski K, Washburn NR (2008) Influence of the degree of methacrylation on hyaluronic acid hydrogels properties. Biomaterials 29(12):1739–1749CrossRef
15.
Zurück zum Zitat Hoch E, Schuh C, Hirth T, Tovar G, Borchers K (2012) Stiff gelatin hydrogels can be photo-chemically synthesized from low viscous gelatin solutions using molecularly functionalized gelatin with a high degree of methacrylation. J Mater Sci Mater Med 23(11):2607–2617CrossRef Hoch E, Schuh C, Hirth T, Tovar G, Borchers K (2012) Stiff gelatin hydrogels can be photo-chemically synthesized from low viscous gelatin solutions using molecularly functionalized gelatin with a high degree of methacrylation. J Mater Sci Mater Med 23(11):2607–2617CrossRef
16.
Zurück zum Zitat Ikladious NE, Asaad JN, Rozik NN (2009) Modification and methacrylation of some new aliphatic hyperbranched polyester polyols based on 1,3,5-Tris(2-hydroxyethyl) cyanuric acid (THECA) as a core. Des Monomers Polym 12:469–481CrossRef Ikladious NE, Asaad JN, Rozik NN (2009) Modification and methacrylation of some new aliphatic hyperbranched polyester polyols based on 1,3,5-Tris(2-hydroxyethyl) cyanuric acid (THECA) as a core. Des Monomers Polym 12:469–481CrossRef
17.
Zurück zum Zitat Dollendorf C, Kreth SK, Choi SW, Ritter H (2013) Polymerization of novel methacrylated anthraquinone dyes. Beilstein J Org Chem 9:453–459CrossRef Dollendorf C, Kreth SK, Choi SW, Ritter H (2013) Polymerization of novel methacrylated anthraquinone dyes. Beilstein J Org Chem 9:453–459CrossRef
18.
Zurück zum Zitat Sriromreun P, Petchsuk A, Opaprakasit M, Opaprakasit P (2013) Standard methods for characterizations of structure and hydrolytic degradation of aliphatic/aromatic copolyesters. Polym Degrad Stab 98(1):169–176CrossRef Sriromreun P, Petchsuk A, Opaprakasit M, Opaprakasit P (2013) Standard methods for characterizations of structure and hydrolytic degradation of aliphatic/aromatic copolyesters. Polym Degrad Stab 98(1):169–176CrossRef
19.
Zurück zum Zitat Dholakiya B (2012) Unsaturated polyester resin for specialty applications. In: Saleh HE-D (ed) Polyester. InTech, p 177 Dholakiya B (2012) Unsaturated polyester resin for specialty applications. In: Saleh HE-D (ed) Polyester. InTech, p 177
Metadaten
Titel
Curable precursors derived from chemical recycling of poly(ethylene terephthalate) and polylactic acid and physical properties of their thermosetting (co)polyesters
verfasst von
O. Torpanyacharn
P. Sukpuang
A. Petchsuk
P. Opaprakasit
M. Opaprakasit
Publikationsdatum
28.04.2017
Verlag
Springer Berlin Heidelberg
Erschienen in
Polymer Bulletin / Ausgabe 1/2018
Print ISSN: 0170-0839
Elektronische ISSN: 1436-2449
DOI
https://doi.org/10.1007/s00289-017-2039-6

Weitere Artikel der Ausgabe 1/2018

Polymer Bulletin 1/2018 Zur Ausgabe

    Marktübersichten

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