Skip to main content
Top

2018 | OriginalPaper | Chapter

Catalytic Systems for the Production of Poly(lactic acid)

Authors : Jeffery A. Byers, Ashley B. Biernesser, Kayla R. Delle Chiaie, Aman Kaur, Jeffrey A. Kehl

Published in: Synthesis, Structure and Properties of Poly(lactic acid)

Publisher: Springer International Publishing

Activate our intelligent search to find suitable subject content or patents.

search-config
loading …

Abstract

Different ways of synthesizing poly(lactic acid) are reviewed. Emphasis is placed on the development of various catalysts for the ring-opening polymerization of lactide, which has become the most common way to access high molecular weight poly(lactic acid). To complement a survey of the best catalysts for this reaction, we discuss the different mechanisms by which these complexes catalyze the ring-opening polymerization of lactide. The chapter concludes with a description of the methods used for stereoselective polymerization of lactide.

Dont have a licence yet? Then find out more about our products and how to get one now:

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!

Literature
2.
go back to reference Moon SI, Lee CW, Miyamoto M, Kimura Y (2000) Melt polycondensation of l-lactic acid with Sn(II) catalysts activated by various proton acids: a direct manufacturing route to high molecular weight poly(l-lactic acid). J Polym Sci A Polym Chem 38(9):1673–1679. doi:10.1002/(SICI)1099-0518(20000501)38:9 CrossRef Moon SI, Lee CW, Miyamoto M, Kimura Y (2000) Melt polycondensation of l-lactic acid with Sn(II) catalysts activated by various proton acids: a direct manufacturing route to high molecular weight poly(l-lactic acid). J Polym Sci A Polym Chem 38(9):1673–1679. doi:10.​1002/​(SICI)1099-0518(20000501)38:​9 CrossRef
3.
go back to reference Moon SI, Lee CW, Tanaguchi I, Miyamoto M, Kimura Y (2001) Melt/solid polycondensation of l-lactic acid: an alternative route to poly(l-lactic acid) with high molecular weight. Polymer 42:5059–5062. doi:10.1016/S0032-3861(00)00889-2 CrossRef Moon SI, Lee CW, Tanaguchi I, Miyamoto M, Kimura Y (2001) Melt/solid polycondensation of l-lactic acid: an alternative route to poly(l-lactic acid) with high molecular weight. Polymer 42:5059–5062. doi:10.​1016/​S0032-3861(00)00889-2 CrossRef
4.
go back to reference Moon SI, Taniguchi I, Miyamoto M, Kimura Y, Lee CW (2001) Synthesis and properties of high-molecular-weight poly(l-lactic acid) by melt/solid polydcondensation under different reaction conditions. High Perform Polym 13:S189–S196. doi:10.1088/0954-0083/13/2/317 CrossRef Moon SI, Taniguchi I, Miyamoto M, Kimura Y, Lee CW (2001) Synthesis and properties of high-molecular-weight poly(l-lactic acid) by melt/solid polydcondensation under different reaction conditions. High Perform Polym 13:S189–S196. doi:10.​1088/​0954-0083/​13/​2/​317 CrossRef
5.
go back to reference Ajioka M, Enomoto K, Suzuki K, Yamaguchi A (1995) Basic properties of polylactic acid produced by the direct condensation polymerization of lactic acid. Bull Chem Soc Jpn 68(8):2125–2131. doi:10.1246/bcsj.68.2125 CrossRef Ajioka M, Enomoto K, Suzuki K, Yamaguchi A (1995) Basic properties of polylactic acid produced by the direct condensation polymerization of lactic acid. Bull Chem Soc Jpn 68(8):2125–2131. doi:10.​1246/​bcsj.​68.​2125 CrossRef
6.
go back to reference Dove AP (2008) Controlled ring-opening polymerisation of cyclic esters: polymer blocks in self-assembled nanostructures. Chem Commun2008 (48):6446–6470. doi:10.1039/b813059k Dove AP (2008) Controlled ring-opening polymerisation of cyclic esters: polymer blocks in self-assembled nanostructures. Chem Commun2008 (48):6446–6470. doi:10.​1039/​b813059k
7.
8.
go back to reference Kricheldorf HR, Berl M, Scharnagl N (1988) Poly(lactones). 9. Polymerization mechanism of metal alkoxide initiated polymerizations of lactide and various lactones. Macromolecules 21(2):286–293. doi:10.1021/ma00180a002 CrossRef Kricheldorf HR, Berl M, Scharnagl N (1988) Poly(lactones). 9. Polymerization mechanism of metal alkoxide initiated polymerizations of lactide and various lactones. Macromolecules 21(2):286–293. doi:10.​1021/​ma00180a002 CrossRef
9.
go back to reference Dubois P, Jacobs C, Jerome R, Teyssie P (1991) Macromolecular engineering of polylactones and polylactides. 4. Mechanism and kinetics of lactide homopolymerization by aluminum isopropoxide. Macromolecules 24(9):2266–2270. doi:10.1021/ma00009a022 CrossRef Dubois P, Jacobs C, Jerome R, Teyssie P (1991) Macromolecular engineering of polylactones and polylactides. 4. Mechanism and kinetics of lactide homopolymerization by aluminum isopropoxide. Macromolecules 24(9):2266–2270. doi:10.​1021/​ma00009a022 CrossRef
11.
go back to reference Masutani K, Kimura Y (2015) PLA synthesis. From the monomer to the polymer. Poly(lactic acid) science and technology: processing, properties, additives and applications. Royal Society of Chemistry, Cambridge, pp 1–36. doi:10.1039/9781782624806-00001 Masutani K, Kimura Y (2015) PLA synthesis. From the monomer to the polymer. Poly(lactic acid) science and technology: processing, properties, additives and applications. Royal Society of Chemistry, Cambridge, pp 1–36. doi:10.​1039/​9781782624806-00001
14.
go back to reference Bourissou D, Martin-Vaca B, Dumitrescu A, Graullier M, Lacombe F (2005) Controlled cationic polymerization of lactide. Macromolecules 38(24):9993–9998. doi:10.1021/ma051646k CrossRef Bourissou D, Martin-Vaca B, Dumitrescu A, Graullier M, Lacombe F (2005) Controlled cationic polymerization of lactide. Macromolecules 38(24):9993–9998. doi:10.​1021/​ma051646k CrossRef
15.
go back to reference Baśko M, Kubisa P (2010) Cationic polymerization of L,l-lactide. J Polym Sci A Polym Chem 48(12):2650–2658CrossRef Baśko M, Kubisa P (2010) Cationic polymerization of L,l-lactide. J Polym Sci A Polym Chem 48(12):2650–2658CrossRef
16.
go back to reference Baśko M, Kubisa P (2007) Polyester oligodiols by cationic AM copolymerization of L,l-lactide and ε-caprolactone initiated by diols. J Polym Sci A Polym Chem 45(14):3090–3097. doi:10.1002/pola.22065 CrossRef Baśko M, Kubisa P (2007) Polyester oligodiols by cationic AM copolymerization of L,l-lactide and ε-caprolactone initiated by diols. J Polym Sci A Polym Chem 45(14):3090–3097. doi:10.​1002/​pola.​22065 CrossRef
17.
go back to reference Chuma A, Horn HW, Swope WC, Pratt RC, Zhang L, Lohmeijer BGG, Wade CG, Waymouth RM, Hedrick JL, Rice JE (2008) The reaction mechanism for the organocatalytic ring-opening polymerization of l-lactide using guanidine-based catalyst: hydrogen-bonded or covalently bound. J Am Chem Soc 130:6749–6754. doi:10.1021/ja0764411 CrossRef Chuma A, Horn HW, Swope WC, Pratt RC, Zhang L, Lohmeijer BGG, Wade CG, Waymouth RM, Hedrick JL, Rice JE (2008) The reaction mechanism for the organocatalytic ring-opening polymerization of l-lactide using guanidine-based catalyst: hydrogen-bonded or covalently bound. J Am Chem Soc 130:6749–6754. doi:10.​1021/​ja0764411 CrossRef
18.
go back to reference Coulembier O, Lohmeijer BGG, Dove AP, Pratt RC, Mespouille L, Culkin DA, Benight SJ, Dubois P, Waymouth RM, Hedrick JL (2006) Alcohol adducts of N-heterocyclic carbenes: latent catalysts for the thermally-controlled living polymerization of cyclic esters. Macromolecules 39:5617–5628. doi:10.1021/ma0611366 CrossRef Coulembier O, Lohmeijer BGG, Dove AP, Pratt RC, Mespouille L, Culkin DA, Benight SJ, Dubois P, Waymouth RM, Hedrick JL (2006) Alcohol adducts of N-heterocyclic carbenes: latent catalysts for the thermally-controlled living polymerization of cyclic esters. Macromolecules 39:5617–5628. doi:10.​1021/​ma0611366 CrossRef
19.
go back to reference Coulembier O, Dove AP, Pratt RC, Sentman AC, Culkin DA, Mespouille L, Dubois P, Waymouth RM, Hedrick JL (2005) Latent, thermally activated organic catalysts for the on-demand living polymerization of lactide. Angew Chem Int Ed 44:4964–4968. doi:10.1002/anie.200500723 CrossRef Coulembier O, Dove AP, Pratt RC, Sentman AC, Culkin DA, Mespouille L, Dubois P, Waymouth RM, Hedrick JL (2005) Latent, thermally activated organic catalysts for the on-demand living polymerization of lactide. Angew Chem Int Ed 44:4964–4968. doi:10.​1002/​anie.​200500723 CrossRef
20.
go back to reference Penczek S, Szymanski R, Duda A, Baran J (2003) Living polymerization of cyclic esters – a route to (bio)degradable polymers. Influence of chain transfer to polymer on livingness. Macromol Symp 201(201):261–269. doi:10.1002/masy.200351129 CrossRef Penczek S, Szymanski R, Duda A, Baran J (2003) Living polymerization of cyclic esters – a route to (bio)degradable polymers. Influence of chain transfer to polymer on livingness. Macromol Symp 201(201):261–269. doi:10.​1002/​masy.​200351129 CrossRef
21.
go back to reference Yu I, Acosta-Ramirez A, Mehrkhodavandi P (2012) Mechanism of living lactide polymerization by dinuclear indium catalysts and its impact on isoselectivity. J Am Chem Soc 134(30):12758–12773. doi:10.1021/ja3048046 CrossRef Yu I, Acosta-Ramirez A, Mehrkhodavandi P (2012) Mechanism of living lactide polymerization by dinuclear indium catalysts and its impact on isoselectivity. J Am Chem Soc 134(30):12758–12773. doi:10.​1021/​ja3048046 CrossRef
25.
go back to reference Chamberlain BM, Jazdzewski BA, Pink M, Hillmyer MA, Tolman WB (2000) Controlled polymerization of dl-lactide and Îμ-caprolactone by structurally well-defined alkoxo-bridged di- and triyttrium(III) complexes. Macromolecules 33(11):3970–3977. doi:10.1021/ma0000834 CrossRef Chamberlain BM, Jazdzewski BA, Pink M, Hillmyer MA, Tolman WB (2000) Controlled polymerization of dl-lactide and Îμ-caprolactone by structurally well-defined alkoxo-bridged di- and triyttrium(III) complexes. Macromolecules 33(11):3970–3977. doi:10.​1021/​ma0000834 CrossRef
26.
go back to reference Wang X, Thevenon A, Brosmer JL, Yu I, Khan SI, Mehrkhodavandi P, Diaconescu PL (2014) Redox control of group 4 metal ring-opening polymerization activity toward l-lactide and epsilon-caprolactone. J Am Chem Soc 136(32):11264–11267. doi:10.1021/ja505883u CrossRef Wang X, Thevenon A, Brosmer JL, Yu I, Khan SI, Mehrkhodavandi P, Diaconescu PL (2014) Redox control of group 4 metal ring-opening polymerization activity toward l-lactide and epsilon-caprolactone. J Am Chem Soc 136(32):11264–11267. doi:10.​1021/​ja505883u CrossRef
27.
go back to reference Cross ED, Allan LEN, Decken A, Shaver MP (2013) Aluminum salen and salan complexes in the ring-opening polymerization of cyclic esters: controlled immortal and copolymerization of rac-β-butyrolactone and rac-lactide. J Polym Sci A Polym Chem 51(5):1137–1146. doi:10.1002/pola.26476 CrossRef Cross ED, Allan LEN, Decken A, Shaver MP (2013) Aluminum salen and salan complexes in the ring-opening polymerization of cyclic esters: controlled immortal and copolymerization of rac-β-butyrolactone and rac-lactide. J Polym Sci A Polym Chem 51(5):1137–1146. doi:10.​1002/​pola.​26476 CrossRef
29.
go back to reference Aida T, Maekawa Y, Asano S, Inoue S (1988) Immortal polymerization – polymerization of epoxide and beta-lactone with aluminum porphyrin in the presence of protic compound. Macromolecules 21(5):1195–1202. doi:10.1021/ma00183a001 CrossRef Aida T, Maekawa Y, Asano S, Inoue S (1988) Immortal polymerization – polymerization of epoxide and beta-lactone with aluminum porphyrin in the presence of protic compound. Macromolecules 21(5):1195–1202. doi:10.​1021/​ma00183a001 CrossRef
30.
go back to reference Ajellal N, Carpentier J-F, Guillaume C, Guillaume SM, Helou M, Poirier V, Sarazin Y, Trifonov A (2010) Metal-catalyzed immortal ring-opening polymerization of lactones, lactides and cyclic carbonates. Dalton Trans 39:8363–8376. doi:10.1039/c001226b CrossRef Ajellal N, Carpentier J-F, Guillaume C, Guillaume SM, Helou M, Poirier V, Sarazin Y, Trifonov A (2010) Metal-catalyzed immortal ring-opening polymerization of lactones, lactides and cyclic carbonates. Dalton Trans 39:8363–8376. doi:10.​1039/​c001226b CrossRef
31.
go back to reference Amgoune A, Thomas CM, Carpentier J-F (2007) Yttrium complexes as catalysts for living and immortal polymerization of lactide to highly heterotactic PLA. Macromol Rapid Commun 28:693–697. doi:10.1002/marc.200600862 CrossRef Amgoune A, Thomas CM, Carpentier J-F (2007) Yttrium complexes as catalysts for living and immortal polymerization of lactide to highly heterotactic PLA. Macromol Rapid Commun 28:693–697. doi:10.​1002/​marc.​200600862 CrossRef
35.
go back to reference Ovitt TM, Coates GW (1999) Stereoselective ring-opening polymerization of meso-lactide: synthesis of syndiotactic poly(lactic acid). J Am Chem Soc 121(16):4072–4073. doi:10.1021/ja990088k CrossRef Ovitt TM, Coates GW (1999) Stereoselective ring-opening polymerization of meso-lactide: synthesis of syndiotactic poly(lactic acid). J Am Chem Soc 121(16):4072–4073. doi:10.​1021/​ja990088k CrossRef
36.
39.
40.
41.
42.
go back to reference Kowalski A, Duda A, Penczek S (1998) Polymerization of l,l-lactide initiated by aluminum isopropoxide trimer or tetramer. Macromolecules 31(7):2114–2122. doi:10.1021/ma971737k CrossRef Kowalski A, Duda A, Penczek S (1998) Polymerization of l,l-lactide initiated by aluminum isopropoxide trimer or tetramer. Macromolecules 31(7):2114–2122. doi:10.​1021/​ma971737k CrossRef
43.
44.
go back to reference Nomura N, Ishii R, Akakura M, Aoi K (2002) Stereoselective ring-opening polymerization of racemic lactide using aluminum-achiral ligand complexes: exploration of a chain-end control mechanism. J Am Chem Soc 124(21):5938–5939. doi:10.1021/ja0175789 CrossRef Nomura N, Ishii R, Akakura M, Aoi K (2002) Stereoselective ring-opening polymerization of racemic lactide using aluminum-achiral ligand complexes: exploration of a chain-end control mechanism. J Am Chem Soc 124(21):5938–5939. doi:10.​1021/​ja0175789 CrossRef
45.
go back to reference Hormnirun P, Marshall EL, Gibson VC, Pugh RI, White AJP (2006) Study of ligand substituent effects on the rate and stereoselectivity of lactide polymerization using aluminum salen-type initiators. Proc Natl Acad Sci 103(42):15343–15348. doi:10.1073/pnas.0602765103 CrossRef Hormnirun P, Marshall EL, Gibson VC, Pugh RI, White AJP (2006) Study of ligand substituent effects on the rate and stereoselectivity of lactide polymerization using aluminum salen-type initiators. Proc Natl Acad Sci 103(42):15343–15348. doi:10.​1073/​pnas.​0602765103 CrossRef
46.
go back to reference Hormnirun P, Marshall EL, Gibson VC, White AJP, Williams DJ (2004) Remarkable stereocontrol in the polymerization of racemic lactide using aluminum initiators supported by tetradentate aminophenoxide ligands. J Am Chem Soc 126(9):2688–2689. doi:10.1021/ja038757o CrossRef Hormnirun P, Marshall EL, Gibson VC, White AJP, Williams DJ (2004) Remarkable stereocontrol in the polymerization of racemic lactide using aluminum initiators supported by tetradentate aminophenoxide ligands. J Am Chem Soc 126(9):2688–2689. doi:10.​1021/​ja038757o CrossRef
47.
go back to reference Kawahara M, Kato-Negishi M (2011) Link between aluminum and the pathogenesis of Alzheimer’s disease: the integration of the aluminum and amyloid cascade hypotheses. Int J Alzheimers Dis 2011:17. doi:10.4061/2011/276393 Kawahara M, Kato-Negishi M (2011) Link between aluminum and the pathogenesis of Alzheimer’s disease: the integration of the aluminum and amyloid cascade hypotheses. Int J Alzheimers Dis 2011:17. doi:10.​4061/​2011/​276393
48.
go back to reference Poirier V, Roisnel T, Carpentier J-F, Sarazin Y (2009) Versatile catalytic systems based on complexes of zinc, magnesium and calcium supported by a bulky bis(morpholinomethyl)phenoxy ligand for the large-scale immortal ring-opening polymerisation of cyclic esters. Dalton Trans 44:9820–9827. doi:10.1039/b917799j CrossRef Poirier V, Roisnel T, Carpentier J-F, Sarazin Y (2009) Versatile catalytic systems based on complexes of zinc, magnesium and calcium supported by a bulky bis(morpholinomethyl)phenoxy ligand for the large-scale immortal ring-opening polymerisation of cyclic esters. Dalton Trans 44:9820–9827. doi:10.​1039/​b917799j CrossRef
49.
go back to reference Chisholm MH, Eilerts NW, Huffman JC, Iyer SS, Pacold M, Phomphrai K (2000) Molecular design of single-site metal alkoxide catalyst precursors for ring-opening polymerization reactions leading to polyoxygenates. 1. Polylactide formation by achiral and chiral magnesium and zinc alkoxides, (eta3-L)MOR, where L = trispyrazolyl- and trisindazolylborate ligands. J Am Chem Soc 122(48):11845–11854. doi:10.1021/ja002160g CrossRef Chisholm MH, Eilerts NW, Huffman JC, Iyer SS, Pacold M, Phomphrai K (2000) Molecular design of single-site metal alkoxide catalyst precursors for ring-opening polymerization reactions leading to polyoxygenates. 1. Polylactide formation by achiral and chiral magnesium and zinc alkoxides, (eta3-L)MOR, where L = trispyrazolyl- and trisindazolylborate ligands. J Am Chem Soc 122(48):11845–11854. doi:10.​1021/​ja002160g CrossRef
50.
go back to reference Cheng M, Attygalle AB, Lobkovsky E, Coates GW (1999) Single-site catalysts for ring-opening polymerization: synthesis of heterotactic poly(lactic acid) from rac-lactide. J Am Chem Soc 121:11583–11584. doi:10.1021/ja992678o CrossRef Cheng M, Attygalle AB, Lobkovsky E, Coates GW (1999) Single-site catalysts for ring-opening polymerization: synthesis of heterotactic poly(lactic acid) from rac-lactide. J Am Chem Soc 121:11583–11584. doi:10.​1021/​ja992678o CrossRef
51.
go back to reference Chamberlain BM, Cheng M, Moore DR, Ovitt TM, Lobkovsky EB, Coates GW (2001) Polymerization of lactide with zinc and magnesium b-diiminate complexes: stereocontrol and mechanism. J Am Chem Soc 123(14):3229–3238. doi:10.1021/ja003851f CrossRef Chamberlain BM, Cheng M, Moore DR, Ovitt TM, Lobkovsky EB, Coates GW (2001) Polymerization of lactide with zinc and magnesium b-diiminate complexes: stereocontrol and mechanism. J Am Chem Soc 123(14):3229–3238. doi:10.​1021/​ja003851f CrossRef
52.
go back to reference Chen H-Y, Peng Y-L, Huang T-H, Sutar AK, Miller SA, Lin C-C (2011) Comparative study of lactide polymerization by zinc alkoxide complexes with a b-diketiminato ligand bearing different substituents. J Mol Catal A Chem 339:61–71. doi:10.1016/j.molcata.2011.02.013 CrossRef Chen H-Y, Peng Y-L, Huang T-H, Sutar AK, Miller SA, Lin C-C (2011) Comparative study of lactide polymerization by zinc alkoxide complexes with a b-diketiminato ligand bearing different substituents. J Mol Catal A Chem 339:61–71. doi:10.​1016/​j.​molcata.​2011.​02.​013 CrossRef
53.
go back to reference Dove AP, Gibson VC, Marshall EL, White AJP, Williams DJ (2004) Magnesium and zinc complexes of a potentially tridentate b-diketiminate ligand. Dalton Trans 2004:570–578. doi:10.1039/B314760F Dove AP, Gibson VC, Marshall EL, White AJP, Williams DJ (2004) Magnesium and zinc complexes of a potentially tridentate b-diketiminate ligand. Dalton Trans 2004:570–578. doi:10.​1039/​B314760F
54.
go back to reference Williams CK, Brooks NR, Hillmyer MA, Tolman WB (2002) Metalloenzyme inspired dizinc catalyst for the polymerization of lactide. Chem Commun 2002:2132–2133. doi:10.1039/b206437e Williams CK, Brooks NR, Hillmyer MA, Tolman WB (2002) Metalloenzyme inspired dizinc catalyst for the polymerization of lactide. Chem Commun 2002:2132–2133. doi:10.​1039/​b206437e
55.
go back to reference Williams CK, Breyfogle LE, Choi SK, Nam W, Young JVG, Hillmyer MA, Tolman WB (2003) A highly active zinc catalyst for the controlled polymerization of lactide. J Am Chem Soc 125:11350–11359. doi:10.1021/ja0359512 CrossRef Williams CK, Breyfogle LE, Choi SK, Nam W, Young JVG, Hillmyer MA, Tolman WB (2003) A highly active zinc catalyst for the controlled polymerization of lactide. J Am Chem Soc 125:11350–11359. doi:10.​1021/​ja0359512 CrossRef
56.
go back to reference Breyfogle LE, Williams CK, Young JVG, Hillmyer MA, Tolman WB (2006) Comparison of structurally analogous Zn2, Co2, and Mg2 catalysts for the polymerization of cyclic esters. Dalton Trans:928–936. doi:10.1039/b507014g Breyfogle LE, Williams CK, Young JVG, Hillmyer MA, Tolman WB (2006) Comparison of structurally analogous Zn2, Co2, and Mg2 catalysts for the polymerization of cyclic esters. Dalton Trans:928–936. doi:10.​1039/​b507014g
57.
go back to reference Jensen TR, Breyfogle LE, Hillmyer MA, Tolman WB (2004) Stereoelective polymerization of d,l-lactide using N-heterocyclic carbene based compounds. Chem Commun 2004:2504–2505. doi:10.1039/b405362a Jensen TR, Breyfogle LE, Hillmyer MA, Tolman WB (2004) Stereoelective polymerization of d,l-lactide using N-heterocyclic carbene based compounds. Chem Commun 2004:2504–2505. doi:10.​1039/​b405362a
58.
go back to reference Wheaton CA, Hayes PG (2010) Cationic zinc complexes: a new class of catalyst for living lactide polymerization at ambient temperature. Chem Commun 46 (44):8404–8406. doi:10.1039/c0cc03463k Wheaton CA, Hayes PG (2010) Cationic zinc complexes: a new class of catalyst for living lactide polymerization at ambient temperature. Chem Commun 46 (44):8404–8406. doi:10.​1039/​c0cc03463k
60.
go back to reference Collins RA, Unruangsri J, Mountford P (2013) Synthesis and rac-lactide ring-opening polymerisation studies of new alkaline earth tetrahydroborate complexes. Dalton Trans 42(3):759–769. doi:10.1039/c2dt32151c CrossRef Collins RA, Unruangsri J, Mountford P (2013) Synthesis and rac-lactide ring-opening polymerisation studies of new alkaline earth tetrahydroborate complexes. Dalton Trans 42(3):759–769. doi:10.​1039/​c2dt32151c CrossRef
61.
go back to reference Ejfler J, Kobylka M, Jerzykiewicz LB, Sobota P (2005) Highly efficient magnesium initiators for lactide polymerization. Dalton Trans 2005(11):2047–2050. doi:10.1039/b503134f Ejfler J, Kobylka M, Jerzykiewicz LB, Sobota P (2005) Highly efficient magnesium initiators for lactide polymerization. Dalton Trans 2005(11):2047–2050. doi:10.​1039/​b503134f
62.
go back to reference Wang L, Ma H (2010) Highly active magnesium initiators for ring-opening polymerization of rac-lactide. Macromolecules 43(16):6535–6537CrossRef Wang L, Ma H (2010) Highly active magnesium initiators for ring-opening polymerization of rac-lactide. Macromolecules 43(16):6535–6537CrossRef
63.
go back to reference Zhong Z, Dijkstra PJ, Birg C, Westerhausen M, Feijen J (2001) A novel and versatile calcium-based initiator system for the ring-opening polymerization of cyclic esters. Macromolecules 34(12):3863–3868. doi:10.1021/ma0019510 CrossRef Zhong Z, Dijkstra PJ, Birg C, Westerhausen M, Feijen J (2001) A novel and versatile calcium-based initiator system for the ring-opening polymerization of cyclic esters. Macromolecules 34(12):3863–3868. doi:10.​1021/​ma0019510 CrossRef
65.
go back to reference Chen H-Y, Mialon L, Abboud KA, Miller SA (2012) Comparative study of lactide polymerization with lithium, sodium, magnesium, and calcium complexes of BHT. Organometallics 31(15):5252–5261. doi:10.1021/om300121c CrossRef Chen H-Y, Mialon L, Abboud KA, Miller SA (2012) Comparative study of lactide polymerization with lithium, sodium, magnesium, and calcium complexes of BHT. Organometallics 31(15):5252–5261. doi:10.​1021/​om300121c CrossRef
66.
go back to reference Tang Z, Chen X, Liang Q, Bian X, Yang L, Piao L, Jing X (2003) Strontium-based initiator system for ring-opening polymerization of cyclic esters. J Polym Sci A Polym Chem 41(13):1934–1941. doi:10.1002/pola.10740 CrossRef Tang Z, Chen X, Liang Q, Bian X, Yang L, Piao L, Jing X (2003) Strontium-based initiator system for ring-opening polymerization of cyclic esters. J Polym Sci A Polym Chem 41(13):1934–1941. doi:10.​1002/​pola.​10740 CrossRef
67.
go back to reference Liu B, Dorcet V, Maron L, Carpentier J-F, Sarazin Y (2012) β-Diketiminato–alkaline earth cationic complexes: synthesis, structures, lactide polymerization and unusual oxidative reactivity of the ancillary ligand. Eur J Inorg Chem 18:3023–3031. doi:10.1002/ejic.201200183 CrossRef Liu B, Dorcet V, Maron L, Carpentier J-F, Sarazin Y (2012) β-Diketiminato–alkaline earth cationic complexes: synthesis, structures, lactide polymerization and unusual oxidative reactivity of the ancillary ligand. Eur J Inorg Chem 18:3023–3031. doi:10.​1002/​ejic.​201200183 CrossRef
68.
go back to reference Davidson MG, O'Hara CT, Jones MD, Keir CG, Mahon MF, Kociok-Kohn G (2007) Synthesis and structure of a molecular barium aminebis(phenolate) and its application as an initiator for ring-opening polymerization of cyclic esters. Inorg Chem 46(19):7686–7688. doi:10.1021/ic700583e CrossRef Davidson MG, O'Hara CT, Jones MD, Keir CG, Mahon MF, Kociok-Kohn G (2007) Synthesis and structure of a molecular barium aminebis(phenolate) and its application as an initiator for ring-opening polymerization of cyclic esters. Inorg Chem 46(19):7686–7688. doi:10.​1021/​ic700583e CrossRef
69.
go back to reference Liu B, Roisnel T, Sarazin Y (2012) Well-defined, solvent-free cationic barium complexes: synthetic strategies and catalytic activity in the ring-opening polymerization of lactide. Inorg Chim Acta 380:2–13. doi:10.1016/j.ica.2011.09.020 CrossRef Liu B, Roisnel T, Sarazin Y (2012) Well-defined, solvent-free cationic barium complexes: synthetic strategies and catalytic activity in the ring-opening polymerization of lactide. Inorg Chim Acta 380:2–13. doi:10.​1016/​j.​ica.​2011.​09.​020 CrossRef
72.
go back to reference Kim Y, Jnaneshwara GK, Verkade JG (2003) Titanium alkoxides as initiators for the controlled polymerization of lactide. Inorg Chem 42(5):1437–1447. doi:10.1021/ic026139n CrossRef Kim Y, Jnaneshwara GK, Verkade JG (2003) Titanium alkoxides as initiators for the controlled polymerization of lactide. Inorg Chem 42(5):1437–1447. doi:10.​1021/​ic026139n CrossRef
74.
go back to reference Zelikoff AL, Kopilov J, Goldberg I, Coates GW, Kol M (2009) New facets of an old ligand: titanium and zirconium complexes of phenylenediamine bis(phenolate) in lactide polymerisation catalysis. Chem Commun 2009 (44):6804–6806. doi:10.1039/b915211c Zelikoff AL, Kopilov J, Goldberg I, Coates GW, Kol M (2009) New facets of an old ligand: titanium and zirconium complexes of phenylenediamine bis(phenolate) in lactide polymerisation catalysis. Chem Commun 2009 (44):6804–6806. doi:10.​1039/​b915211c
75.
go back to reference Sauer A, Kapelski A, Fliedel C, Dagorne S, Kol M, Okuda J (2012) Structurally well-defined group 4 metal complexes as initiators for the ring-opening polymerization of lactide monomers. Dalton Trans 42(25):9007–9023. doi:10.1039/c3dt00010a CrossRef Sauer A, Kapelski A, Fliedel C, Dagorne S, Kol M, Okuda J (2012) Structurally well-defined group 4 metal complexes as initiators for the ring-opening polymerization of lactide monomers. Dalton Trans 42(25):9007–9023. doi:10.​1039/​c3dt00010a CrossRef
76.
go back to reference Saha TK, Ramkumar V, Chakraborty D (2011) Salen complexes of zirconium and hafnium: synthesis, structural characterization, controlled hydrolysis, and solvent-free ring-opening polymerization of cyclic esters and lactides. Inorg Chem 50(7):2720–2722. doi:10.1021/ic1025262 CrossRef Saha TK, Ramkumar V, Chakraborty D (2011) Salen complexes of zirconium and hafnium: synthesis, structural characterization, controlled hydrolysis, and solvent-free ring-opening polymerization of cyclic esters and lactides. Inorg Chem 50(7):2720–2722. doi:10.​1021/​ic1025262 CrossRef
77.
go back to reference Chmura AJ, Davidson MG, Frankis CJ, Jones MD, Lunn MD (2008) Highly active and stereoselective zirconium and hafnium alkoxide initiators for solvent-free ring-opening polymerization of rac-lactide. Chem Commun 2008 11:1293–1295. doi:10.1039/b718678a Chmura AJ, Davidson MG, Frankis CJ, Jones MD, Lunn MD (2008) Highly active and stereoselective zirconium and hafnium alkoxide initiators for solvent-free ring-opening polymerization of rac-lactide. Chem Commun 2008 11:1293–1295. doi:10.​1039/​b718678a
78.
go back to reference Romain C, Heinrich B, Laponnaz SB, Dagorne S (2012) A robust zirconium N-heterocyclic carbene complex for the living and highly stereoselective ring-opening polymerization of rac-lactide. Chem Commun 48(16):2213–2215. doi:10.1039/c2cc16819g CrossRef Romain C, Heinrich B, Laponnaz SB, Dagorne S (2012) A robust zirconium N-heterocyclic carbene complex for the living and highly stereoselective ring-opening polymerization of rac-lactide. Chem Commun 48(16):2213–2215. doi:10.​1039/​c2cc16819g CrossRef
79.
go back to reference El-Zoghbi I, Whitehorne TJJ, Schaper F (2013) Exceptionally high lactide polymerization activity of zirconium complexes with bridged diketiminate ligands. Dalton Trans 42(25):9376–9387. doi:10.1039/c2dt31761c CrossRef El-Zoghbi I, Whitehorne TJJ, Schaper F (2013) Exceptionally high lactide polymerization activity of zirconium complexes with bridged diketiminate ligands. Dalton Trans 42(25):9376–9387. doi:10.​1039/​c2dt31761c CrossRef
80.
go back to reference Sergeeva E, Kopilov J, Goldberg I, Kol M (2010) Dithiodiolate ligands: group 4 complexes and application in lactide polymerization. Inorg Chem 49(9):3977–3979. doi:10.1021/ic100390x CrossRef Sergeeva E, Kopilov J, Goldberg I, Kol M (2010) Dithiodiolate ligands: group 4 complexes and application in lactide polymerization. Inorg Chem 49(9):3977–3979. doi:10.​1021/​ic100390x CrossRef
81.
go back to reference Horeglad P, Szczepaniak G, Dranka M, Zachara J (2012) The first facile stereoselectivity switch in the polymerization of rac-lactide-from heteroselective to isoselective dialkylgallium alkoxides with the help of N-heterocyclic carbenes. Chem Commun 48(8):1171–1173. doi:10.1039/c2cc16072b CrossRef Horeglad P, Szczepaniak G, Dranka M, Zachara J (2012) The first facile stereoselectivity switch in the polymerization of rac-lactide-from heteroselective to isoselective dialkylgallium alkoxides with the help of N-heterocyclic carbenes. Chem Commun 48(8):1171–1173. doi:10.​1039/​c2cc16072b CrossRef
82.
go back to reference Bakewell C, White AJP, Long NJ, Williams CK (2013) 8-Quinolinolato gallium complexes: iso-selective initiators for rac-lactide polymerization. Inorg Chem 52(21):12561–12567. doi:10.1021/ic4016756 CrossRef Bakewell C, White AJP, Long NJ, Williams CK (2013) 8-Quinolinolato gallium complexes: iso-selective initiators for rac-lactide polymerization. Inorg Chem 52(21):12561–12567. doi:10.​1021/​ic4016756 CrossRef
84.
go back to reference Pietrangelo A, Knight SC, Gupta AK, Yao LJ, Hillmyer MA, Tolman WB (2010) Mechanistic study of the stereoselective polymerization of d,l-lactide using indium(III) halides. J Am Chem Soc 132(33):11649–11657. doi:10.1021/ja103841h CrossRef Pietrangelo A, Knight SC, Gupta AK, Yao LJ, Hillmyer MA, Tolman WB (2010) Mechanistic study of the stereoselective polymerization of d,l-lactide using indium(III) halides. J Am Chem Soc 132(33):11649–11657. doi:10.​1021/​ja103841h CrossRef
85.
go back to reference Kowalski A, Duda A, Penczek S (2000) Kinetics and mechanism of cyclic esters polymerization initiated with tin(II) octanoate. 3. Polymerizaiton of L,l-dilactide. Macromolecules 33:7359–7370. doi:10.1021/ma000125o CrossRef Kowalski A, Duda A, Penczek S (2000) Kinetics and mechanism of cyclic esters polymerization initiated with tin(II) octanoate. 3. Polymerizaiton of L,l-dilactide. Macromolecules 33:7359–7370. doi:10.​1021/​ma000125o CrossRef
86.
go back to reference Kowalski A, Duda A, Penczek S (2000) Mechanism of cyclic ester polymerization initiated with tin(II) octoate 2. Macromolecules fitted with tin(II) alkoxide species observed directly in MALDI-TOF spectra. Macromolecules 33:689–695. doi:10.1021/ma9906940 CrossRef Kowalski A, Duda A, Penczek S (2000) Mechanism of cyclic ester polymerization initiated with tin(II) octoate 2. Macromolecules fitted with tin(II) alkoxide species observed directly in MALDI-TOF spectra. Macromolecules 33:689–695. doi:10.​1021/​ma9906940 CrossRef
88.
go back to reference Dove AP, Gibson VC, Marshall EL, Rzepa HS, White AJP, Williams DJ (2006) Synthetic, structural, mechanistic, and computational studies on single-site b-diketiminate tin(II) initiators for the polymerization of rac-lactide. J Am Chem Soc 128(30):9834–9843. doi:10.1021/ja061400a CrossRef Dove AP, Gibson VC, Marshall EL, Rzepa HS, White AJP, Williams DJ (2006) Synthetic, structural, mechanistic, and computational studies on single-site b-diketiminate tin(II) initiators for the polymerization of rac-lactide. J Am Chem Soc 128(30):9834–9843. doi:10.​1021/​ja061400a CrossRef
89.
go back to reference Nimitsiriwat N, Marshall EL, Gibson VC, Elsegood MRJ, Dale SH (2004) Unprecedented reversible migration of amide to Schiff base ligands attached to tin: latent single-site initiators for lactide polymerization. J Am Chem Soc 126(42):13598–13599. doi:10.1021/ja0470315 CrossRef Nimitsiriwat N, Marshall EL, Gibson VC, Elsegood MRJ, Dale SH (2004) Unprecedented reversible migration of amide to Schiff base ligands attached to tin: latent single-site initiators for lactide polymerization. J Am Chem Soc 126(42):13598–13599. doi:10.​1021/​ja0470315 CrossRef
90.
91.
go back to reference Poirier V, Roisnel T, Sinbandhit S, Bochmann M, Carpentier J-F, Sarazin Y (2012) Synthetic and mechanistic aspects of the immortal ring-opening polymerization of lactide and trimethylene carbonate with new homo- and heteroleptic tin(II)-phenolate catalysts. Chem Eur J 18(10):2998–3013. doi:10.1002/chem.201102261 CrossRef Poirier V, Roisnel T, Sinbandhit S, Bochmann M, Carpentier J-F, Sarazin Y (2012) Synthetic and mechanistic aspects of the immortal ring-opening polymerization of lactide and trimethylene carbonate with new homo- and heteroleptic tin(II)-phenolate catalysts. Chem Eur J 18(10):2998–3013. doi:10.​1002/​chem.​201102261 CrossRef
92.
93.
go back to reference Chmura AJ, Chuck CJ, Davidson MG, Jones MD, Lunn MD, Bull SD, Mahon MF (2007) A germanium alkoxide supported by a C3-symmetric ligand for the stereoselective synthesis of highly heterotactic polylactide under solvent-free conditions. Angew Chem 119(13):2330–2333. doi:10.1002/ange.200603944 CrossRef Chmura AJ, Chuck CJ, Davidson MG, Jones MD, Lunn MD, Bull SD, Mahon MF (2007) A germanium alkoxide supported by a C3-symmetric ligand for the stereoselective synthesis of highly heterotactic polylactide under solvent-free conditions. Angew Chem 119(13):2330–2333. doi:10.​1002/​ange.​200603944 CrossRef
94.
go back to reference Guo J, Haquette P, Martin J, Salim K, Thomas CM (2013) Replacing tin in lactide polymerization: design of highly active germanium-based catalysts. Angew Chem Int Ed 52(51):13584–13587. doi:10.1002/anie.201306623 CrossRef Guo J, Haquette P, Martin J, Salim K, Thomas CM (2013) Replacing tin in lactide polymerization: design of highly active germanium-based catalysts. Angew Chem Int Ed 52(51):13584–13587. doi:10.​1002/​anie.​201306623 CrossRef
95.
go back to reference Hoppe JO, Agnew Marcelli MG, Tainter ML (1955) A review of the toxicity of iron compounds. Am J Med Sci 230(5):558–571CrossRef Hoppe JO, Agnew Marcelli MG, Tainter ML (1955) A review of the toxicity of iron compounds. Am J Med Sci 230(5):558–571CrossRef
96.
go back to reference Stolt M, Sodergard A (1999) Use of monocarboxylic iron derivatives in the ring-opening polymerization of l-lactide. Macromolecules 32(20):6412–6417. doi:10.1021/ma9902753 CrossRef Stolt M, Sodergard A (1999) Use of monocarboxylic iron derivatives in the ring-opening polymerization of l-lactide. Macromolecules 32(20):6412–6417. doi:10.​1021/​ma9902753 CrossRef
98.
101.
go back to reference O'Keefe BJ, Monnier SM, Hillmyer MA, Tolman WB (2000) Rapid and controlled polymerization of lactide by structurally characterized ferric alkoxides. J Am Chem Soc 123(2):339–340. doi:10.1021/ja003537l CrossRef O'Keefe BJ, Monnier SM, Hillmyer MA, Tolman WB (2000) Rapid and controlled polymerization of lactide by structurally characterized ferric alkoxides. J Am Chem Soc 123(2):339–340. doi:10.​1021/​ja003537l CrossRef
102.
103.
go back to reference McGuinness DS, Marshall EL, Gibson VC, Steed JW (2003) Anionic iron(II) alkoxides as initiators for the controlled ring-opening polymerization of lactide. J Polym Sci A Polym Chem 41(23):3798–3803. doi:10.1002/pola.10946 CrossRef McGuinness DS, Marshall EL, Gibson VC, Steed JW (2003) Anionic iron(II) alkoxides as initiators for the controlled ring-opening polymerization of lactide. J Polym Sci A Polym Chem 41(23):3798–3803. doi:10.​1002/​pola.​10946 CrossRef
104.
go back to reference Gibson VC, Marshall EL, Navarro-Llobet D, White AJP, Williams DJ (2002) A well-defined iron(ii) alkoxide initiator for the controlled polymerisation of lactide. J Chem Soc Dalton Trans 2002 (23):4321–4322. doi:10.1039/b209703f Gibson VC, Marshall EL, Navarro-Llobet D, White AJP, Williams DJ (2002) A well-defined iron(ii) alkoxide initiator for the controlled polymerisation of lactide. J Chem Soc Dalton Trans 2002 (23):4321–4322. doi:10.​1039/​b209703f
105.
go back to reference Biernesser AB, Li B, Byers JA (2013) Redox-controlled polymerization of lactide catalyzed by bis(imino)pyridine iron bis(alkoxide) complexes. J Am Chem Soc 135(44):16553–16560. doi:10.1021/ja407920d CrossRef Biernesser AB, Li B, Byers JA (2013) Redox-controlled polymerization of lactide catalyzed by bis(imino)pyridine iron bis(alkoxide) complexes. J Am Chem Soc 135(44):16553–16560. doi:10.​1021/​ja407920d CrossRef
106.
107.
go back to reference Sun J, Shi W, Chen D, Liang C (2002) The ring-opening polymerization of d,l-lactide catalyzed by new complexes of Cu, Zn, Co, and Ni Schiff base derived from salicylidene and l-aspartic acid. J Appl Polym Sci 86(13):3312–3315. doi:10.1002/app.11234 CrossRef Sun J, Shi W, Chen D, Liang C (2002) The ring-opening polymerization of d,l-lactide catalyzed by new complexes of Cu, Zn, Co, and Ni Schiff base derived from salicylidene and l-aspartic acid. J Appl Polym Sci 86(13):3312–3315. doi:10.​1002/​app.​11234 CrossRef
109.
go back to reference Chen l-L, Ding l-Q, Zeng C, Long Y, Lü X-Q, Song J-R, Fan D-D, Jin W-J (2011) Bulk solvent-free melt ring-opening polymerization of l-lactide catalyzed by Cu(II) and Cu(II)–Nd(III) complexes of the salen-type Schiff-base ligand. Appl Organomet Chem 25(4):310–316. doi:10.1002/aoc.1760 CrossRef Chen l-L, Ding l-Q, Zeng C, Long Y, Lü X-Q, Song J-R, Fan D-D, Jin W-J (2011) Bulk solvent-free melt ring-opening polymerization of l-lactide catalyzed by Cu(II) and Cu(II)–Nd(III) complexes of the salen-type Schiff-base ligand. Appl Organomet Chem 25(4):310–316. doi:10.​1002/​aoc.​1760 CrossRef
110.
go back to reference John A, Katiyar V, Pang K, Shaikh MM, Nanavati H, Ghosh P (2007) Ni(II) and Cu(II) complexes of phenoxy-ketimine ligands: synthesis, structures and their utility in bulk ring-opening polymerization (ROP) of l-lactide. Polyhedron 26(15):4033–4044. doi:10.1016/j.poly.2007.04.039 CrossRef John A, Katiyar V, Pang K, Shaikh MM, Nanavati H, Ghosh P (2007) Ni(II) and Cu(II) complexes of phenoxy-ketimine ligands: synthesis, structures and their utility in bulk ring-opening polymerization (ROP) of l-lactide. Polyhedron 26(15):4033–4044. doi:10.​1016/​j.​poly.​2007.​04.​039 CrossRef
111.
go back to reference Whitehorne TJJ, Schaper F (2012) Nacnac BnCuOiPr: a strained geometry resulting in very high lactide polymerization activity. Chem Commun 48(83):10334–10336. doi:10.1039/c2cc34247b CrossRef Whitehorne TJJ, Schaper F (2012) Nacnac BnCuOiPr: a strained geometry resulting in very high lactide polymerization activity. Chem Commun 48(83):10334–10336. doi:10.​1039/​c2cc34247b CrossRef
112.
115.
go back to reference Daneshmand P, Schaper F (2015) Exploring the reactivity of manganese(iii) complexes with diphenolate-diamino ligands in rac-lactide polymerization. Dalton Trans 44(47):20449–20458. doi:10.1039/c5dt03756e CrossRef Daneshmand P, Schaper F (2015) Exploring the reactivity of manganese(iii) complexes with diphenolate-diamino ligands in rac-lactide polymerization. Dalton Trans 44(47):20449–20458. doi:10.​1039/​c5dt03756e CrossRef
116.
go back to reference Ding L, Jin W, Chu Z, Chen L, Lü X, Yuan G, Song J, Fan D, Bao F (2011) Bulk solvent-free melt ring-opening polymerization (ROP) of l-lactide catalyzed by Ni(II) and Ni(II)-Ln(III) complexes based on the acyclic salen-type Schiff-base ligand. Inorg Chem Commun 14(8):1274–1278. doi:10.1016/j.inoche.2011.04.040 CrossRef Ding L, Jin W, Chu Z, Chen L, Lü X, Yuan G, Song J, Fan D, Bao F (2011) Bulk solvent-free melt ring-opening polymerization (ROP) of l-lactide catalyzed by Ni(II) and Ni(II)-Ln(III) complexes based on the acyclic salen-type Schiff-base ligand. Inorg Chem Commun 14(8):1274–1278. doi:10.​1016/​j.​inoche.​2011.​04.​040 CrossRef
117.
go back to reference Balasanthiran V, Chatterjee C, Chisholm MH, Harrold ND, Rajan Babu TV, Warren GA (2015) Coupling of propylene oxide and lactide at a porphyrin chromium(III) center. J Am Chem Soc 137(5):1786–1789. doi:10.1021/ja512554t CrossRef Balasanthiran V, Chatterjee C, Chisholm MH, Harrold ND, Rajan Babu TV, Warren GA (2015) Coupling of propylene oxide and lactide at a porphyrin chromium(III) center. J Am Chem Soc 137(5):1786–1789. doi:10.​1021/​ja512554t CrossRef
118.
go back to reference Kim Y, Kapoor PN, Verkade JG (2002) (RO)2Ta[tris(2-oxy-3,5-dimethylbenzyl)amine]: structure and lactide polymerization activities. Inorg Chem 41(18):4834–4838. doi:10.1021/ic0257571 CrossRef Kim Y, Kapoor PN, Verkade JG (2002) (RO)2Ta[tris(2-oxy-3,5-dimethylbenzyl)amine]: structure and lactide polymerization activities. Inorg Chem 41(18):4834–4838. doi:10.​1021/​ic0257571 CrossRef
123.
go back to reference Guillaume SM, Kirillov E, Sarazin Y, Carpentier J-F (2015) Beyond stereoselectivity, switchable catalysis: some of the last frontier challenges in ring-opening polymerization of cyclic esters. Chem Eur J 21(22):7988–8003. doi:10.1002/chem.201500613 CrossRef Guillaume SM, Kirillov E, Sarazin Y, Carpentier J-F (2015) Beyond stereoselectivity, switchable catalysis: some of the last frontier challenges in ring-opening polymerization of cyclic esters. Chem Eur J 21(22):7988–8003. doi:10.​1002/​chem.​201500613 CrossRef
125.
go back to reference Gregson CKA, Gibson VC, Long NJ, Marshall EL, Oxford PJ, White AJP (2006) Redox control within single-site polymerization catalysts. J Am Chem Soc 128(23):7410–7411. doi:10.1021/ja061398n CrossRef Gregson CKA, Gibson VC, Long NJ, Marshall EL, Oxford PJ, White AJP (2006) Redox control within single-site polymerization catalysts. J Am Chem Soc 128(23):7410–7411. doi:10.​1021/​ja061398n CrossRef
126.
go back to reference Brown LA, Rhinehart JL, Long BK (2015) Effects of ferrocenyl proximity and monomer presence during oxidation for the redox-switchable polymerization of l-lactide. ACS Catal 5(10):6057–6060. doi:10.1021/acscatal.5b01434 CrossRef Brown LA, Rhinehart JL, Long BK (2015) Effects of ferrocenyl proximity and monomer presence during oxidation for the redox-switchable polymerization of l-lactide. ACS Catal 5(10):6057–6060. doi:10.​1021/​acscatal.​5b01434 CrossRef
127.
go back to reference Broderick EM, Guo N, Vogel CS, Xu C, Sutter J, Miller JT, Meyer K, Mehrkhodovandi P, Diaconescu PL (2011) Redox control of a ring-opening polymerization catalyst. J Am Chem Soc 133:9278–9281. doi:10.1021/ja2036089 CrossRef Broderick EM, Guo N, Vogel CS, Xu C, Sutter J, Miller JT, Meyer K, Mehrkhodovandi P, Diaconescu PL (2011) Redox control of a ring-opening polymerization catalyst. J Am Chem Soc 133:9278–9281. doi:10.​1021/​ja2036089 CrossRef
128.
go back to reference Broderick EM, Guo N, Wu T, Vogel CS, Xu C, Sutter J, Miller JT, Meyer K, Cantat T, Diaconescu PL (2011) Redox control of a polymerization catalyst by changing the oxidation state of the metal center. Chem Commun 47:9897–9899. doi:10.1039/c1cc13117f CrossRef Broderick EM, Guo N, Wu T, Vogel CS, Xu C, Sutter J, Miller JT, Meyer K, Cantat T, Diaconescu PL (2011) Redox control of a polymerization catalyst by changing the oxidation state of the metal center. Chem Commun 47:9897–9899. doi:10.​1039/​c1cc13117f CrossRef
129.
go back to reference Sauer A, Buffet J-C, Spaniol TP, Nagae H, Mashima K, Okuda J (2013) Switching the lactide polymerization activity of a cerium complex by redox reactions. ChemCatChem 5:1088–1091. doi:10.1002/cctc.201200705 CrossRef Sauer A, Buffet J-C, Spaniol TP, Nagae H, Mashima K, Okuda J (2013) Switching the lactide polymerization activity of a cerium complex by redox reactions. ChemCatChem 5:1088–1091. doi:10.​1002/​cctc.​201200705 CrossRef
130.
go back to reference Biernesser AB, Delle Chiaie KR, Curley JB, Byers JA (2016) Block copolymerization of lactide and an epoxide facilitated by a redox switchable iron-based catalyst. Angew Chem Int Ed 55:5251–5254. doi:10.1002/anie.201511793 CrossRef Biernesser AB, Delle Chiaie KR, Curley JB, Byers JA (2016) Block copolymerization of lactide and an epoxide facilitated by a redox switchable iron-based catalyst. Angew Chem Int Ed 55:5251–5254. doi:10.​1002/​anie.​201511793 CrossRef
131.
go back to reference Delle Chiaie KR, Yablon LM, Biernesser AB, Michalowski GR, Sudyn AW, Byers JA (2016) Redox-triggered crosslinking of a degradable polymer. Polym Chem 7:4675–4681. doi:10.1039/c6py00975a Delle Chiaie KR, Yablon LM, Biernesser AB, Michalowski GR, Sudyn AW, Byers JA (2016) Redox-triggered crosslinking of a degradable polymer. Polym Chem 7:4675–4681. doi:10.​1039/​c6py00975a
133.
go back to reference Lohmeijer BGG, Pratt RC, Leibfarth FA, Logan JW, Long DA, Dove AP, Nederberg F, Choi J, Wade CG, Waymouth RM, Hedrick JL (2006) Guanidine and amidine organocatalysts for ring-opening polymerization of cyclic esters. Macromolecules 39(25):8574–8583. S0024-9297(06)01938-3CrossRef Lohmeijer BGG, Pratt RC, Leibfarth FA, Logan JW, Long DA, Dove AP, Nederberg F, Choi J, Wade CG, Waymouth RM, Hedrick JL (2006) Guanidine and amidine organocatalysts for ring-opening polymerization of cyclic esters. Macromolecules 39(25):8574–8583. S0024-9297(06)01938-3CrossRef
134.
go back to reference 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(14):4556–4557. S0002-7863(06)00662-7CrossRef 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(14):4556–4557. S0002-7863(06)00662-7CrossRef
135.
go back to reference Li H, Zhang S, Jiao J, Jiao Z, Kong L, Xu J, Li J, Zuo J, Zhao X (2009) Controlled synthesis of polylactides using biogenic creatinine carboxylate initiators. Biomacromolecules 10(5):1311–1314. doi:10.1021/bm801479p CrossRef Li H, Zhang S, Jiao J, Jiao Z, Kong L, Xu J, Li J, Zuo J, Zhao X (2009) Controlled synthesis of polylactides using biogenic creatinine carboxylate initiators. Biomacromolecules 10(5):1311–1314. doi:10.​1021/​bm801479p CrossRef
137.
go back to reference Vreese RD, D’hooghe M (2012) N-heterocyclic carbene/Brønsted acid cooperative catalysis as a powerful tool in organic synthesis. Beilstein J Org Chem 8(1):398–402. doi:10.3762/bjoc.8.43 CrossRef Vreese RD, D’hooghe M (2012) N-heterocyclic carbene/Brønsted acid cooperative catalysis as a powerful tool in organic synthesis. Beilstein J Org Chem 8(1):398–402. doi:10.​3762/​bjoc.​8.​43 CrossRef
139.
go back to reference Connor EF, Nyce GW, Myers M, Möck 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(6):914–915. S0002-7863(01)07332-2CrossRef Connor EF, Nyce GW, Myers M, Möck 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(6):914–915. S0002-7863(01)07332-2CrossRef
140.
go back to reference Culkin DA, Jeong W, Csihony S, Gomez ED, Balsara NP, Hedrick JL, Waymouth RM (2007) Zwitterionic polymerization of lactide to cyclic poly(lactide) by using N-heterocyclic carbene organocatalysts. Angew Chem Int Ed 46(15):2627–2630. doi:10.1002/anie.200604740 CrossRef Culkin DA, Jeong W, Csihony S, Gomez ED, Balsara NP, Hedrick JL, Waymouth RM (2007) Zwitterionic polymerization of lactide to cyclic poly(lactide) by using N-heterocyclic carbene organocatalysts. Angew Chem Int Ed 46(15):2627–2630. doi:10.​1002/​anie.​200604740 CrossRef
141.
go back to reference Jeong W, Shin EJ, Culkin DA, Hedrick JL, Waymouth RM (2009) Zwitterionic polymerization: a kinetic strategy for the controlled synthesis of cyclic polylactide. J Am Chem Soc 131(13):4884–4891. doi:10.1021/ja809617v CrossRef Jeong W, Shin EJ, Culkin DA, Hedrick JL, Waymouth RM (2009) Zwitterionic polymerization: a kinetic strategy for the controlled synthesis of cyclic polylactide. J Am Chem Soc 131(13):4884–4891. doi:10.​1021/​ja809617v CrossRef
142.
go back to reference Zhang L, Nederberg F, Pratt RC, Waymouth RM, Hedrick JL, Wade CG (2007) Phosphazene bases: a new category of organocatalysts for the living ring-opening polymerization of cyclic esters. Macromolecules 40(12):4154–4158. doi:10.1021/ma070316s CrossRef Zhang L, Nederberg F, Pratt RC, Waymouth RM, Hedrick JL, Wade CG (2007) Phosphazene bases: a new category of organocatalysts for the living ring-opening polymerization of cyclic esters. Macromolecules 40(12):4154–4158. doi:10.​1021/​ma070316s CrossRef
143.
go back to reference Zhang L, Nederberg F, Messman JM, Pratt RC, Hedrick JL, Wade CG (2007) Organocatalytic stereoselective ring-opening polymerization of lactide with dimeric phosphazene bases. J Am Chem Soc 129:12610–12611. S0002-7863(07)04131-5CrossRef Zhang L, Nederberg F, Messman JM, Pratt RC, Hedrick JL, Wade CG (2007) Organocatalytic stereoselective ring-opening polymerization of lactide with dimeric phosphazene bases. J Am Chem Soc 129:12610–12611. S0002-7863(07)04131-5CrossRef
144.
go back to reference Thomas C, Peruch F, Deffieux A, Milet A, Desvergne J-P, Bibal B (2011) Phenols and tertiary amines: an amazingly simple hydrogen bonding organocatalytic system promoting ring opening polymerization. Adv Synth Catal 353:1049–1054. doi:10.1002/adsc.201100013 CrossRef Thomas C, Peruch F, Deffieux A, Milet A, Desvergne J-P, Bibal B (2011) Phenols and tertiary amines: an amazingly simple hydrogen bonding organocatalytic system promoting ring opening polymerization. Adv Synth Catal 353:1049–1054. doi:10.​1002/​adsc.​201100013 CrossRef
145.
go back to reference Alba A, Schopp A, Delgado A-PDS, Cherif-Cheikh R, Martin-Vaca B, Bourissou D (2010) Controlled ring-opening polymerization of lactide by bis-sulfonamide/amine associations: cooperative hydrogen-bonding catalysis. J Polym Sci A Polym Chem 48:959–965. doi:10.1002/pola.23852 CrossRef Alba A, Schopp A, Delgado A-PDS, Cherif-Cheikh R, Martin-Vaca B, Bourissou D (2010) Controlled ring-opening polymerization of lactide by bis-sulfonamide/amine associations: cooperative hydrogen-bonding catalysis. J Polym Sci A Polym Chem 48:959–965. doi:10.​1002/​pola.​23852 CrossRef
146.
go back to reference Coulembier O, Sanders DP, Nelson A, Hollenbeck AN, Horn HW, Rice JE, Fujiwara M, Dubois P, Hedrick JL (2009) Hydrogen-bonding catalysts based on fluorinated alcohol derivatives for living polymerization. Angew Chem Int Ed 48:5170–5173. doi:10.1002/anie.200901006 CrossRef Coulembier O, Sanders DP, Nelson A, Hollenbeck AN, Horn HW, Rice JE, Fujiwara M, Dubois P, Hedrick JL (2009) Hydrogen-bonding catalysts based on fluorinated alcohol derivatives for living polymerization. Angew Chem Int Ed 48:5170–5173. doi:10.​1002/​anie.​200901006 CrossRef
147.
go back to reference Koeller S, Kadota J, Deffieux A, Peruch F, Massip S, Leger J-M, Desvergne J-P, Bibal B (2009) Ring opening polymerization of l-lactide efficiently triggered by an amido-indole. X-ray structure of a complex between l-lactide and the hydrogen-bonding organocatalyst. J Am Chem Soc 131:15088–15089. doi:10.1021/ja906119t CrossRef Koeller S, Kadota J, Deffieux A, Peruch F, Massip S, Leger J-M, Desvergne J-P, Bibal B (2009) Ring opening polymerization of l-lactide efficiently triggered by an amido-indole. X-ray structure of a complex between l-lactide and the hydrogen-bonding organocatalyst. J Am Chem Soc 131:15088–15089. doi:10.​1021/​ja906119t CrossRef
148.
go back to reference Pratt RC, Lohmeijer BGG, Long DA, Lundberg PNP, Dove AP, Li H, Wade CG, Waymouth RM, Hedrick JL (2006) Exploration, optimization, and application of supramolecular thiourea-amine catalysts for the synthesis of lactide (co)polymers. Macromolecules 39:7863–7871. doi:10.1021/ma061607o CrossRef Pratt RC, Lohmeijer BGG, Long DA, Lundberg PNP, Dove AP, Li H, Wade CG, Waymouth RM, Hedrick JL (2006) Exploration, optimization, and application of supramolecular thiourea-amine catalysts for the synthesis of lactide (co)polymers. Macromolecules 39:7863–7871. doi:10.​1021/​ma061607o CrossRef
149.
go back to reference Liu J, Chen C, Li Z, Wu W, Zhi X, Zhang Q, Wu H, Wang X, Cui S, Guo K (2015) A squaramide and tertiary amine: an excellent hydrogen-bonding pair organocatalyst for living polymerization. Polym Chem 6(20):3754–3757. doi:10.1039/C5PY00508F CrossRef Liu J, Chen C, Li Z, Wu W, Zhi X, Zhang Q, Wu H, Wang X, Cui S, Guo K (2015) A squaramide and tertiary amine: an excellent hydrogen-bonding pair organocatalyst for living polymerization. Polym Chem 6(20):3754–3757. doi:10.​1039/​C5PY00508F CrossRef
150.
go back to reference Zhi X, Liu J, Li Z, Wang H, Wang X, Cui S, Chen C, Zhao C, Li X, Guo K (2016) Ionic hydrogen bond donor organocatalyst for fast living ring-opening polymerization. Polym Chem 7(2):339–349. doi:10.1039/C5PY01315A CrossRef Zhi X, Liu J, Li Z, Wang H, Wang X, Cui S, Chen C, Zhao C, Li X, Guo K (2016) Ionic hydrogen bond donor organocatalyst for fast living ring-opening polymerization. Polym Chem 7(2):339–349. doi:10.​1039/​C5PY01315A CrossRef
151.
go back to reference Thomas C, Milet A, Peruch F, Bibal B (2013) Activation of carbonyl bonds by quaternary ammoniums and a (Na+:crown-ether) complex: investigation of the ring-opening polymerization of cyclic esters. Polym Chem 4(12):3491–3498. doi:10.1039/C3PY00304C CrossRef Thomas C, Milet A, Peruch F, Bibal B (2013) Activation of carbonyl bonds by quaternary ammoniums and a (Na+:crown-ether) complex: investigation of the ring-opening polymerization of cyclic esters. Polym Chem 4(12):3491–3498. doi:10.​1039/​C3PY00304C CrossRef
152.
go back to reference Koeller S, Thomas C, Peruch F, Deffieux A, Massip S, Léger J-M, Desvergne J-P, Milet A, Bibal B (2014) α-Halogenoacetanilides as hydrogen-bonding organocatalysts that activate carbonyl bonds: fluorine versus chlorine and bromine. Chem 20(10):2849–2859. doi:10.1002/chem.201303662 CrossRef Koeller S, Thomas C, Peruch F, Deffieux A, Massip S, Léger J-M, Desvergne J-P, Milet A, Bibal B (2014) α-Halogenoacetanilides as hydrogen-bonding organocatalysts that activate carbonyl bonds: fluorine versus chlorine and bromine. Chem 20(10):2849–2859. doi:10.​1002/​chem.​201303662 CrossRef
153.
go back to reference Zhang D, Jardel D, Peruch F, Calin N, Dufaud V, Dutasta J-P, Martinez A, Bibal B (2016) Azaphosphatranes as hydrogen-bonding organocatalysts for the activation of carbonyl groups: investigation of lactide ring-opening polymerization. Eur J Org Chem 2016(8):1619–1624. doi:10.1002/ejoc.201600080 CrossRef Zhang D, Jardel D, Peruch F, Calin N, Dufaud V, Dutasta J-P, Martinez A, Bibal B (2016) Azaphosphatranes as hydrogen-bonding organocatalysts for the activation of carbonyl groups: investigation of lactide ring-opening polymerization. Eur J Org Chem 2016(8):1619–1624. doi:10.​1002/​ejoc.​201600080 CrossRef
154.
go back to reference Makiguchi K, Kikuchi S, Yanai K, Ogasawara Y, S-i S, Satoh T, Kakuchi T (2014) Diphenyl phosphate/4-dimethylaminopyridine as an efficient binary organocatalyst system for controlled/living ring-opening polymerization of l-lactide leading to diblock and end-functionalized poly(l-lactide)s. J Polym Sci A Polym Chem 52(7):1047–1054. doi:10.1002/pola.27089 CrossRef Makiguchi K, Kikuchi S, Yanai K, Ogasawara Y, S-i S, Satoh T, Kakuchi T (2014) Diphenyl phosphate/4-dimethylaminopyridine as an efficient binary organocatalyst system for controlled/living ring-opening polymerization of l-lactide leading to diblock and end-functionalized poly(l-lactide)s. J Polym Sci A Polym Chem 52(7):1047–1054. doi:10.​1002/​pola.​27089 CrossRef
155.
go back to reference 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(40):13798–13799. S0002-7863(05)04334-9CrossRef 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(40):13798–13799. S0002-7863(05)04334-9CrossRef
156.
go back to reference Miyake GM, Chen EY-X (2011) Cinchona alkaloids as stereoselective organocatalysts for the partial kinetic resolution polymerization of rac-lactide. Macromolecules 44(11):4116–4124. doi:10.1021/ma2007199 CrossRef Miyake GM, Chen EY-X (2011) Cinchona alkaloids as stereoselective organocatalysts for the partial kinetic resolution polymerization of rac-lactide. Macromolecules 44(11):4116–4124. doi:10.​1021/​ma2007199 CrossRef
157.
go back to reference Patel D, Liddle ST, Mungur SA, Rodden M, Blake AJ, Arnold PL (2006) Bifunctional yttrium(III) and titanium(IV) NHC catalysts for lactide polymerisation. Chem Commun 2006(10):1124–1126. doi:10.1039/B514406J Patel D, Liddle ST, Mungur SA, Rodden M, Blake AJ, Arnold PL (2006) Bifunctional yttrium(III) and titanium(IV) NHC catalysts for lactide polymerisation. Chem Commun 2006(10):1124–1126. doi:10.​1039/​B514406J
158.
go back to reference Thakur KAM, Kean RT, Hall ES, Kolstad JJ, Lindgren TA (1997) High-resolution 13C and 1H solution NMR study of poly(lactide). Macromolecules 30:2422–2428CrossRef Thakur KAM, Kean RT, Hall ES, Kolstad JJ, Lindgren TA (1997) High-resolution 13C and 1H solution NMR study of poly(lactide). Macromolecules 30:2422–2428CrossRef
159.
go back to reference Zell MT, Padden BE, Paterick AJ, Thakur KAM, Kean RT, Hillmyer MA, Munson EJ (2002) Unambiguous determination of the 13C and 1H NMR stereosequence assignments of polylactide using high-resolution solution NMR spectroscopy. Macromolecules 35(20):7700–7707. doi:10.1021/ma0204148 CrossRef Zell MT, Padden BE, Paterick AJ, Thakur KAM, Kean RT, Hillmyer MA, Munson EJ (2002) Unambiguous determination of the 13C and 1H NMR stereosequence assignments of polylactide using high-resolution solution NMR spectroscopy. Macromolecules 35(20):7700–7707. doi:10.​1021/​ma0204148 CrossRef
160.
161.
go back to reference Dieter A, Schluter CH, Sakamoto J (2012) Synthesis of polymers: new structures and methods. Wiley, Weinheim Dieter A, Schluter CH, Sakamoto J (2012) Synthesis of polymers: new structures and methods. Wiley, Weinheim
162.
go back to reference Chisholm MH, Patmore NJ, Zhou Z (2004) Concerning the relative importance of enantiomorphic site vs. chain end control in the stereoselective polymerization of lactides: reactions of (R,R-salen)- and (S,S-salen)-aluminium alkoxides LAlOCH2R complexes (R = CH3 and S-CHMeCl). Chem Commun:127–129. doi:10.1039/B413266A Chisholm MH, Patmore NJ, Zhou Z (2004) Concerning the relative importance of enantiomorphic site vs. chain end control in the stereoselective polymerization of lactides: reactions of (R,R-salen)- and (S,S-salen)-aluminium alkoxides LAlOCH2R complexes (R = CH3 and S-CHMeCl). Chem Commun:127–129. doi:10.​1039/​B413266A
163.
go back to reference Pilone A, Press K, Goldberg I, Kol M, Mazzeo M, Lamberti M (2014) Gradient isotactic multiblock polylactides from aluminum complexes of chiral salalen ligands. J Am Chem Soc 136(8):2940–2943. doi:10.1021/ja412798x CrossRef Pilone A, Press K, Goldberg I, Kol M, Mazzeo M, Lamberti M (2014) Gradient isotactic multiblock polylactides from aluminum complexes of chiral salalen ligands. J Am Chem Soc 136(8):2940–2943. doi:10.​1021/​ja412798x CrossRef
164.
go back to reference Ewen JA (1984) Mechanisms of stereochemical control in propylene polymerizations with soluble group 4B metallocene/methylalumoxane catalysts. J Am Chem Soc 106:6355–6364CrossRef Ewen JA (1984) Mechanisms of stereochemical control in propylene polymerizations with soluble group 4B metallocene/methylalumoxane catalysts. J Am Chem Soc 106:6355–6364CrossRef
165.
go back to reference Chisholm MH, Iyer SS, McCollum DG, Pagel M, Werner-Zwanziger U (1999) Microstructure of poly(lactide). Phase-sensitive HETCOR spectra of poly(meso-lactide), poly(rac-lactide), and atactic poly(lactide). Macromolecules 32(4):963–973. doi:10.1021/ma9806864 CrossRef Chisholm MH, Iyer SS, McCollum DG, Pagel M, Werner-Zwanziger U (1999) Microstructure of poly(lactide). Phase-sensitive HETCOR spectra of poly(meso-lactide), poly(rac-lactide), and atactic poly(lactide). Macromolecules 32(4):963–973. doi:10.​1021/​ma9806864 CrossRef
166.
go back to reference Ovitt TM, Coates GW (2002) Stereochemistry of lactide polymerization with chiral catalysts: new opportunities for stereocontrol using polymer exchange mechanisms. J Am Chem Soc 124(7):1316–1326. doi:10.1021/ja012052+ CrossRef Ovitt TM, Coates GW (2002) Stereochemistry of lactide polymerization with chiral catalysts: new opportunities for stereocontrol using polymer exchange mechanisms. J Am Chem Soc 124(7):1316–1326. doi:10.​1021/​ja012052+ CrossRef
168.
169.
go back to reference Spassky N, Wisniewski M, Pluta C, Le Borgne A (1996) Highly stereoelective polymerization of rac-(d,l)-lactide with a chiral schiff’s base/aluminium alkoxide initiator. Macromol Chem Phys 197(9):2627–2637. doi:10.1002/macp.1996.021970902 CrossRef Spassky N, Wisniewski M, Pluta C, Le Borgne A (1996) Highly stereoelective polymerization of rac-(d,l)-lactide with a chiral schiff’s base/aluminium alkoxide initiator. Macromol Chem Phys 197(9):2627–2637. doi:10.​1002/​macp.​1996.​021970902 CrossRef
170.
go back to reference Du H, Velders AH, Dijkstra PJ, Sun J, Zhong Z, Chen X, Feijen J (2009) Chiral salan aluminium ethyl complexes and their application in lactide polymerization. Chem 15(38):9836–9845. doi:10.1002/chem.200900799 CrossRef Du H, Velders AH, Dijkstra PJ, Sun J, Zhong Z, Chen X, Feijen J (2009) Chiral salan aluminium ethyl complexes and their application in lactide polymerization. Chem 15(38):9836–9845. doi:10.​1002/​chem.​200900799 CrossRef
171.
go back to reference Jones MD, Hancock SL, McKeown P, Schafer PM, Buchard A, Thomas LH, Mahon MF, Lowe JP (2014) Zirconium complexes of bipyrrolidine derived salan ligands for the isoselective polymerisation of rac-lactide. Chem Commun 50(100):15967–15970. doi:10.1039/c4cc07871c CrossRef Jones MD, Hancock SL, McKeown P, Schafer PM, Buchard A, Thomas LH, Mahon MF, Lowe JP (2014) Zirconium complexes of bipyrrolidine derived salan ligands for the isoselective polymerisation of rac-lactide. Chem Commun 50(100):15967–15970. doi:10.​1039/​c4cc07871c CrossRef
172.
go back to reference Honrado M, Otero A, Fernandez-Baeza J, Sanchez-Barba LF, Garces A, Lara-Sanchez A, Rodriguez AM (2014) Stereoselective ROP of rac-lactide mediated by enantiopure NNO-scorpionate zinc initiators. Organometallics 33(7):1859–1866. doi:10.1021/om500207x CrossRef Honrado M, Otero A, Fernandez-Baeza J, Sanchez-Barba LF, Garces A, Lara-Sanchez A, Rodriguez AM (2014) Stereoselective ROP of rac-lactide mediated by enantiopure NNO-scorpionate zinc initiators. Organometallics 33(7):1859–1866. doi:10.​1021/​om500207x CrossRef
173.
go back to reference Aluthge DC, Patrick BO, Mehrkhodavandi P (2013) A highly active and site selective indium catalyst for lactide polymerization. Chem Commun 49(39):4295–4297. doi:10.1039/c2cc33519k CrossRef Aluthge DC, Patrick BO, Mehrkhodavandi P (2013) A highly active and site selective indium catalyst for lactide polymerization. Chem Commun 49(39):4295–4297. doi:10.​1039/​c2cc33519k CrossRef
174.
go back to reference Ma H, Spaniol TP, Okuda J (2006) Highly heteroselective ring-opening polymerization of rac-lactide initiated by bis(phenolato)scandium complexes. Angew Chem Int Ed 45(46):7818–7821CrossRef Ma H, Spaniol TP, Okuda J (2006) Highly heteroselective ring-opening polymerization of rac-lactide initiated by bis(phenolato)scandium complexes. Angew Chem Int Ed 45(46):7818–7821CrossRef
175.
go back to reference Manna CM, Kaur A, Yablon LM, Haeffner F, Li B, Byers JA (2015) Stereoselective catalysis achieved through in situ desymmetrization of an achiral iron catalyst precursor. J Am Chem Soc 137(45):14232–14235. doi:10.1021/jacs.5b09966 CrossRef Manna CM, Kaur A, Yablon LM, Haeffner F, Li B, Byers JA (2015) Stereoselective catalysis achieved through in situ desymmetrization of an achiral iron catalyst precursor. J Am Chem Soc 137(45):14232–14235. doi:10.​1021/​jacs.​5b09966 CrossRef
176.
go back to reference Nomura N, Hasegawa J, Ishii R (2009) A direct function relationship between isotacticity and melting temperature of multiblock stereocopolymer poly(rac-lactide). Macromolecules 42(13):4907–4909. doi:10.1021/ma900760z CrossRef Nomura N, Hasegawa J, Ishii R (2009) A direct function relationship between isotacticity and melting temperature of multiblock stereocopolymer poly(rac-lactide). Macromolecules 42(13):4907–4909. doi:10.​1021/​ma900760z CrossRef
177.
go back to reference Pilone A, Maio ND, Press K, Venditto V, Pappalardo D, Mazzeo M, Pellecchia C, Kol M, Lamberti M (2015) Ring-opening homo- and co-polymerization of lactides and ε-caprolactone by salalen aluminum complexes. Dalton Trans 44(5):2157–2165. doi:10.1039/C4DT02616K Pilone A, Maio ND, Press K, Venditto V, Pappalardo D, Mazzeo M, Pellecchia C, Kol M, Lamberti M (2015) Ring-opening homo- and co-polymerization of lactides and ε-caprolactone by salalen aluminum complexes. Dalton Trans 44(5):2157–2165. doi:10.​1039/​C4DT02616K
178.
go back to reference Vieira IS, Whitelaw EL, Jones MD, Herres-Pawlis S (2013) Synergistic empirical and theoretical study on the stereoselective mechanism for the aluminum salalen complex mediated polymerization of rac-lactide. Chem 19(15):4712–4716. doi:10.1002/chem.201203973 CrossRef Vieira IS, Whitelaw EL, Jones MD, Herres-Pawlis S (2013) Synergistic empirical and theoretical study on the stereoselective mechanism for the aluminum salalen complex mediated polymerization of rac-lactide. Chem 19(15):4712–4716. doi:10.​1002/​chem.​201203973 CrossRef
179.
go back to reference Dove AP, Gibson VC, Marshall EL, Rzepa HS, White AJP, Williams DJ (2006) Synthetic, structural, mechanistic, and computational studies on single-site β-diketiminate Tin(II) initiators for the polymerization of rac-lactide. J Am Chem Soc 128(30):9834–9843. S0002-7863(06)01400-4CrossRef Dove AP, Gibson VC, Marshall EL, Rzepa HS, White AJP, Williams DJ (2006) Synthetic, structural, mechanistic, and computational studies on single-site β-diketiminate Tin(II) initiators for the polymerization of rac-lactide. J Am Chem Soc 128(30):9834–9843. S0002-7863(06)01400-4CrossRef
180.
go back to reference Mou Z, Liu B, Wang M, Xie H, Li P, Li L, Li S, Cui D (2014) Isoselective ring-opening polymerization of rac-lactide initiated by achiral heteroscorpionate zwitterionic zinc complexes. Chem Commun 50:11411–11414. doi:10.1039/C4CC05033A CrossRef Mou Z, Liu B, Wang M, Xie H, Li P, Li L, Li S, Cui D (2014) Isoselective ring-opening polymerization of rac-lactide initiated by achiral heteroscorpionate zwitterionic zinc complexes. Chem Commun 50:11411–11414. doi:10.​1039/​C4CC05033A CrossRef
184.
186.
go back to reference Gruber PR, Kolstad JJ, Hall ES, Conn RSE, Ryan CM (1994) Melt-stable lactide polymer composition and process for manufacture thereof. Patent US5981694 A Gruber PR, Kolstad JJ, Hall ES, Conn RSE, Ryan CM (1994) Melt-stable lactide polymer composition and process for manufacture thereof. Patent US5981694 A
187.
go back to reference De Vos SC (2009) Method for manufacturing stable polylactide. Patent US20090247710 A1 De Vos SC (2009) Method for manufacturing stable polylactide. Patent US20090247710 A1
188.
go back to reference Gruber PR, Hall ES, Kolstad JJ, Iwen ML, Benson RD, Borchardt RL (1993) Continuous process for the manufacture of lactide and lactide polymers. Patent WO1993015127 Gruber PR, Hall ES, Kolstad JJ, Iwen ML, Benson RD, Borchardt RL (1993) Continuous process for the manufacture of lactide and lactide polymers. Patent WO1993015127
189.
go back to reference Shinoda H, Ohtaguro M, Iimuro S (1993) Modified polyester composition and preparation process and use thereof. Patent EP0608921 A2 Shinoda H, Ohtaguro M, Iimuro S (1993) Modified polyester composition and preparation process and use thereof. Patent EP0608921 A2
190.
go back to reference Spinu M (1994) Manufacture of polylactide stereocomplexes. Patent US07989048 Spinu M (1994) Manufacture of polylactide stereocomplexes. Patent US07989048
191.
go back to reference Fedushkin IL, Chudakova VA, Cherkasov VK (2010) Catalyst and method for polymerization and copolymerization of lactide. Patent WO2008128548 A2 Fedushkin IL, Chudakova VA, Cherkasov VK (2010) Catalyst and method for polymerization and copolymerization of lactide. Patent WO2008128548 A2
192.
go back to reference Chang WC, Sun WH (2002) Method of polymerization of lactide and polylactide homopolymer thereof. Patent US6376643 B1 Chang WC, Sun WH (2002) Method of polymerization of lactide and polylactide homopolymer thereof. Patent US6376643 B1
193.
go back to reference Fridman ID, Kwok J, Downey RJ, Nemphos SP (1994) Lactide polymerization. Patent US5357034 A Fridman ID, Kwok J, Downey RJ, Nemphos SP (1994) Lactide polymerization. Patent US5357034 A
194.
go back to reference Ohara HCOSC, Sawa SCOSC, Kawamoto TCOSC (1995) Method for producing polylactic acid. Patent US5508378 A Ohara HCOSC, Sawa SCOSC, Kawamoto TCOSC (1995) Method for producing polylactic acid. Patent US5508378 A
195.
go back to reference Williams CK, Romain C, Kember M (2014) Method and catalyst system for preparing polymers and block copolymers. Patent US20160108181 A1 Williams CK, Romain C, Kember M (2014) Method and catalyst system for preparing polymers and block copolymers. Patent US20160108181 A1
196.
go back to reference Gobius DSG, Davidson MG, Chuck CJ (2014) Method to manufacture PLA using a new polymerization catalyst. Patent US20160075821 A1 Gobius DSG, Davidson MG, Chuck CJ (2014) Method to manufacture PLA using a new polymerization catalyst. Patent US20160075821 A1
197.
go back to reference Drysdale NE, Ford TM, Mclain SJ (1993) Polymerization of lactide with rare-earth metal catalysts. Patent WO1993018080 A1 Drysdale NE, Ford TM, Mclain SJ (1993) Polymerization of lactide with rare-earth metal catalysts. Patent WO1993018080 A1
198.
go back to reference Coady DJ, Fukushima K, Hedrick JL, Horn HW, Rice JE (2014) Methods of ring opening polymerization and catalysts therefor. Patent US8846851 B2 Coady DJ, Fukushima K, Hedrick JL, Horn HW, Rice JE (2014) Methods of ring opening polymerization and catalysts therefor. Patent US8846851 B2
199.
go back to reference Dong H, Esser-Kahn AP, Thakre PR, Patrick JF, Sottos NR, White SR, Moore JS (2012) Chemical treatment of poly(lactic acid) fibers to enhance the rate of thermal depolymerization. ACS Appl Mater Interfaces 4:503–509. doi:10.1021/am2010042 CrossRef Dong H, Esser-Kahn AP, Thakre PR, Patrick JF, Sottos NR, White SR, Moore JS (2012) Chemical treatment of poly(lactic acid) fibers to enhance the rate of thermal depolymerization. ACS Appl Mater Interfaces 4:503–509. doi:10.​1021/​am2010042 CrossRef
Metadata
Title
Catalytic Systems for the Production of Poly(lactic acid)
Authors
Jeffery A. Byers
Ashley B. Biernesser
Kayla R. Delle Chiaie
Aman Kaur
Jeffrey A. Kehl
Copyright Year
2018
DOI
https://doi.org/10.1007/12_2017_20

Premium Partners